US2674619A - Polyoxyalkylene compounds - Google Patents
Polyoxyalkylene compounds Download PDFInfo
- Publication number
- US2674619A US2674619A US386945A US38694553A US2674619A US 2674619 A US2674619 A US 2674619A US 386945 A US386945 A US 386945A US 38694553 A US38694553 A US 38694553A US 2674619 A US2674619 A US 2674619A
- Authority
- US
- United States
- Prior art keywords
- polyoxypropylene
- compounds
- groups
- molecular weight
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
- B01D19/0413—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance compounds containing N-atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/42—Amino alcohols or amino ethers
- C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/06—Protein or carboxylic compound containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/07—Organic amine, amide, or n-base containing
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Polyethers (AREA)
Description
April 6, 1954 Filed 001.- 19. 1953 CARBON SOIL REMOVAL a1 I40F, ZOF STANDARD '6 8 (D O POLYOXYALKYLENE COMPOUNDS FiG. l
| s. LUNDSTED 2,674,619
3 Sheets-Sheet 1 ZOIO Lester G. Lundstod INVENTOR.
April 6,
Filed Oct.
CARBON SOIL REMOVAL of 90 E,% OF STANDARD L. G. LUNDSTED POLYOXYALKYLENE COMPOUNDS 3 Sheets-Sheet 2 FIG. 2
Loner G. Lands-n6 INVENTOR.
omey
A nl 6, 1954 L. e. LUNDSTED 2,674,619
POLYOXYALKYLENE COMPOUNDS Filed Oct. 19, 1955 3 Sheets-Sheet 3 FIG. 3
23l0 POLYOXYPROPYLENE POLYMER BASE I270 H'LYOXYPROPYLENE POLYMER BASE DARD cARBou son. REMOVAL m I40F, 10F STAN i OXYETHYLENE WENT Lane 6. Lundugg Patented Apr. 6, 1954 POLYOXYALKYLENE COMPOUNDS Lester G. Lundsted, Grosse Ile, Mich, assignor to Wyandotte Chemicals Corporation, Wyandotte, Mich., a corporation of Michigan Application October 19, 1953, Serial No. 386,945
18 Claims. 1
This invention relates to a group of novel polyoxyalkylene compounds which have outstandin detergent and surface active properties, and in which the hydrophobic element is a polyoxypropylene polymer having a molecular weight of at least 900. This application is a continuationin-part of my copending application, Serial No. 316,984, filed October 27, 1952, which is a continuation-in-part of my earlier filed application Serial No. 153,946, filed April 4, 1950, both applications now abandoned.
The art of producing surface active agents is old and well-developed, and it is a, well-recognized principle that all such compounds are relatively large molecules which contain both hydrophobic and hydrophilic elements. The essential hydrophobic element in the prior art surface active agents has always been a hydrocarbon radical, such as found in the long chain fatty acids and alcohols, or in the alkylaryl group of the popular alkylarylsulfonate type detergents. The hydrophllic element has frequently been a polyoxyethylene chain, such as found in nonylphenolethylene oxide condensation products.
A serious limitation of the prior art surface active agents is that the structure of any particular surface active agent is relatively fixed and it is diflicult to modify it, either as to molecular weight or the relative proportion by weight of the hydrophilic to the hydrophobic element. To prepare fatty alcohol based surface active agents having varying hydrophobic element chain lengths, it is necessary to use as many different starting materials as there are variations desired. Amon the difficulties inherent in using several starting materials are the storage and handling of many types of complex organic compounds, supply problems as to rare homologues, the different reaction conditions required in preparing the surface active agents, etc., so that it is not feasible to prepare surface active agents which differ from one another in small, uniform increments of hydrophobic element chain length. Similar difflculties are encountered in preparing petroleum based surface active agents which differ from each other only in small, finite increments of hydrophobic element chain length.
A further shortcoming of prior art nonionic surface active agents is that all the highly active compounds are liquids or pastes. While the physical form of a surface active agent does not effect its surface active properties, convenience in packaging, distribution and use makes a solid form highly desirable.
Several United States Patents, e. g. 2,213,447;
2,454,434 and 2,454,542-545, teach the use of poly oxyalkylene chains in surface active agents, but in all such patents the polyoxyalkylene chain constitutes the hydrophilic element of the surface active compound. U. S. Patent No. 2,425,845 discloses heteric or mixed polyoxyalkylene glycols, such as those which are formed when a mixture of ethylene and propylene oxides is condensed with a monoalkylene glycol, but these compounds do not possess detergent properties. It has also been previously known to react a higher aliphatic, water-insoluble monohydric alcohol sequentially with propylene oxide and ethylene oxide (U. S. Patent No. 2,174,761). The molecular weight of the polyoxypropylene chain in such a compound, even at its maximum theoretical value, is well below the minimum polyoxypropylene polymer molecular weight which has been found necessary in order to achiev the excellent detergent properties which characterize the compounds of the present invention.
It is an object of this invention to prepare novel polyoxyalkylene compounds having outstanding detergent and surface active properties and in which the hydrophobic element is a polyoxypropylene polymer.
Another object of this invention is to provide novel polyoxyalkylene compounds having excellent detergent and surface active properties and in which the molecular weight of both the hydrophobic and the hydrophilic element can b simultaneously varied within wide limits.
A further object of this invention is to provide nonionic detergents of high activity in a solid form.
Other objects and advantages of this invention will become apparent from the following detailed description thereof when read in conjunction with the accompanying drawings, in which:
Fig. 1 is a graph showing the effect of the polyoxypropylene polymer molecular weight upon detergent properties in 140 F. water,
Fig. 2 is a graph showing the efiect of the polyoxypnopylene polymer molecular weight upon detergent properties in 90 F. water, and
Fig. 3 is a. graph showing the effect of variation of polyoxyethylene content on detergent properties in 140 F. water.
NATURE OF INVENTION A new class of polyoxyalkylene compounds has been discovered which have outstanding detergent and surface active properties and in which the hydrophobic element is a polyoxypropylene polymer of at least 900 molecular weight. The
Y is the residue of an organic compound containing therein r active hydrogen atoms,
n is an integer,
a: is an integer greater than 1,
The values of n and a: are such that the molecular weight of the compound, exclusive of E, is at least 900, as determined by hydroxyl number,
E is a polyoxyalkylene chain wherein th oxygen/ carbon atom ratio is at least 0.5, and E constitutes 20-90%, by weight, of the compound.
The significance of each element of the above generic formula will be set forth in the subsequent sections of this patent.
STRUCTURE OF THE NOVEL POLYOXYAL- KYLENE COMPOUNDS The polyoxypropylene polymer, which is an intermediate in the preparation of the compounds of this invention, has the following structure;
-O(CIHQO LE! 2):
wherein n is'defined as in FormulaA.
The preferred compounds of this invention are prepared by condensing ethylene oxide, in an amount constituting 20 90% of the resultant compound, with the poiyoxypropylene polymer. Thus, these compounds have the following formula:
(C) Y[ (CaHsO) (021140) mH]:
where 'Y, n and a: are deflnedasin Formula A and rm-has a value such that'the oxyethylene groups constitute 20-90%, by weight, of the compound. When ethyleneoxide is condensed with a polyoxypropylene glycol of at least 900 molecular weight, the resulting compounds have the following structure:
where m and n are definedas previously set forth. When ethylene oxide is condensed with a D 5- oxypropylene polymer that is derived by the condensation oi" propylene oxide with adipic acid,
the resulting compounds have the following structure:
with m and n being defined as previously described.
The hydrophilic portion of the novel polyoxyalkylene compounds may be supplied by other polyoxyalkylene chains in lieu of the polyoxyethylene chain set forth in Formula C. Any polyoxyalkylene chain may be used provided that the oxygen/carbon atom ratio contained therein is at least 0.5. For example, such hydrophllic polyoxyalkylene chain may be derived from butadiene dioxide, glycidol, etc. By letting the symbol E represent generically any such polyoxyalkylene chain, Formula C may be rewritten as Formula A by simply substituting E for (CzHrOM. Formula A represents the broad generic class of compounds to which the present invention relates.
PREPARATION OF THE NOVEL POLYOXY- ALKYLENE COMPOUNDS The preparation of the surface active agents of this invention involves two steps:
1. The condensation of propylene oxide with a base compound containing a plurality of reactive hydrogen atoms to prepare a polyoxypropylene polymer of at least 900 molecular weight, and
2. The condensation of ethylene oxide, or its equivalent, with the polyoxypropylene polymer.
In the first step propylene oxide is condensed with the base compound containing the plurality of reactive hydrogen atoms to prepare the polyoxypropylene polymer, viz:
Hereinafter the base compound containing a plurality of reactive hydrogen atoms will be referred to simply as the reactive hydrogen compound. Alternatively, if desired, the polyoxypropylene polymer may be prepared by reacting a polyoxypropylene glycol with the reactive hydrogen compound, by esterification, etherification, etc. de pending upon the nature of the reactive hydrogen compound, viz:
In the second step of the preparation, the hydrophilic polyoxyalkylene chain is introduced into the molecule by condensing ethylene oxide, or its equivalent, with the polyoxypropylene polymer, viz:
As an alternative procedure the hydrophilic polyoxyalkylene chain may be introduced by etherifying the polyoxypropylene polymer with a polyoxyethylene glycol, or its equivalent.
In preparing the polyoxypropylene polymer, the condensation of propylene oxide with the reactive hydrogen compound is normally carried out at elevated temperatures and pressures in the presence of an alkaline catalyst such as sodium alkoxide, a quaternary ammonium base, or preferably sodium hydroxide. Similarly, the condensation reaction may be carried out in the presence of acid catalysts as set forth in U. 8. Patent No. 2,510,540.
Although the reaction may be carried out by simply heating a mixture of the reactants under pressure at a sufficiently high temperature, this procedure is not ordinarily used as the temperatures and pressures required are excessive and control of the reaction is diflicult. For each mol of propylene oxide reacting, an estimated 25 kilogram-calories of heat is liberated which, in the presence of a large quantity of propylene oxide, may increase the temperature and reaction rate to such an extent that the reaction assumes an explosive nature.
The preferred method of carrying out the reaction is to add the propylene oxide to a stirred, heated mixture of the de sired reactive hydrogen compound and alkaline catalyst in a sealed reaction vessel. By adding the propylene oxide to the reaction vessel at such a rate that it reacts as rapidly as added, an excess of propylene oxide is avoided and control of the reaction is simplifled.
The temperature at which the reaction is run will depend upon the particular system in qucs tion and especially upon the catalyst concentration used. Generally, at higher catalyst concer1- trations the reaction can be run at lower temperatures and correspondingly lower pressures. The temperatures and pressures required for any given reaction will vary with the reactive hydrogen compound. and the typ and concentration of catalyst used.
The condensation of ethylene oxide with the polyoxypropylene polymer is carried out in an analogous manner.
The preparation of the novel polyoxyalkylene compounds of the invention is illustrated by Example 1 below:
EXAMPLE 1.PAxr A In a one-liter 3-neck round bottom flask equipped with a mechanical stirrer, reflux condenser, thermometer and propylene oxide feed inlet, there were placed 5'7 grams (0.75 mol) of propylene glycol and 7.5 grams of anhydrous sodium hydroxide. The flask was purged with nitrogen to remove air and heated to 120 C. with stirring, and until the sodium hydroxide was dissolved. Then sufficient propylene oxide was introduced into the mixture as fast as it would react until the product possessed a calculated molecular weight of 2380. The product was cooled under nitrogen, the NaOIil catalyst neutralized with sulfuric acid and the product filtered. The final product was a water-insoluble polyoxypropylene glycol having an average molecular weight of 1620 as determined by hydroxyl number or acetylation analytical test procedure.
EXAMYLE 1.-PART B five grams of ethylene oxide was added at an average temperature of 120 C., using the same technique as employed in Part A. The amount of added ethylene oxide corresponded to 17.4 of the total weight of the polyoxypropylene glycol base plus the weight ofadded ethylene oxide.
of the composition It will be noted in Part A of the above example that the molecular weight, as determined by bydroxyl number, was appreciably lower than the calculated molecular weight. Throughout this application, unless otherwise specified, it will be understood that the molecular weight of the polyoxypropylene polymer was determined by hydroxyl number using the method of Ogg et al., Industrial and Engineering Chemistry, Analytical Ed., vol. 17, p. 395, 1945.
EVALUATION TEST FOR SURFACE ACTIVITY The following test procedure was used to evaluate the surface active properties of the products of this invention:
Carbon soil removal test procedure A standard soiled cotton fabric is first prepared as follows:
Bleached, unfinished Indian Head muslin (58 x 47, 4.7 oz. per sq. yd., manufactured by Textron, Inc.) is used without pretreatment after conditioning to equilibrium at R. H. and F. A continuous 10 inch wide strip of the muslin is soiled by passing through an emulsion of colloidal carbon black and water-soluble mineral oil. After thorough impregnation of the standard muslin in the carbon black and oil emulsion, the cloth is passed through a powerrlriven household -type wringer to squeeze out any residual aqueous dispersion, the wringer pressure being so adjusted as to leave in the cloth an amount of standard soil dispersion equal to j:5% of the dry weight of the cloth. The
soiled muslin is then passed through a brush arrangement which by means of its mechanical action on the cloth controls the removability characteristics of the soil. The soiled muslin or test cloth is then dried, first in festoon under atmospheric conditions and then in an electrically heated, forced draft oven. After drying, the cloth is aged for 4 to 6 days by hanging in an atmosphere of 65% R. H. at 70 F. after which it is cut into test swatches measuring 2.5 inches-:
' inch by 3.5 1110118513 1 inch using a power driven guillotine paper cutter. Before actual use of the so-prepared standard soiled cloth, it is checked for conformance with acceptability limits by the following described carbon soil removal test in standard detergent solutions. The swatches are stored at 65% R. H. and 70 F. prior to use.
To evaluate the soil removal characteristics of synthetic detergent compositions, 0.25% by weight solutions or other desired concentrations to be tested are prepared in water and 100 ml. portions of such solution are added to each of 10 one-pint jars of a Launder- Ometer (type l2Q-EF-SPA, manufactured by Atlas Electric Devices Company) standard laundry test machine.
Fifteen A" diameter stainless steel balls are placed in each jar, after which two pieces of the previously prepared standard soiled cloth are added to each of nine jars. In the tenth jar are placed two pieces of unsoiled but pretreated cloth and this latter jar serves as a blank for deter" mining the turbidity of the detergent solution. The so-prepared jars, heated to a temperature of :2 F. in a constant temperature bath are then placed in the Launder-Ometer" and run for 10 minutes at a speed of 4212 R. P. M. The jars are then removed from the test machines and replaced in the constant temperature bath. The contents of each jar to which the standard 7 soiled cloth has been added? acoarse screen to separate the standard soiled cloth fro the soil suspension which is collected in a large beaker. The composite suspension thus attained is mixed thoroughly and a sample placed in a mm. light absorption cell. The light absorption of this composite solution. as well as the light absorption oi the solution in the tenth or blank jar containing the unsoiled cloth test pieces is then measured (by Lumetron Colorimeter). By means of a calibration curve for the "Lumetron Colorimeter, such curve being constructed by obtaining light transmission readings of known quantities of carbon black dispersion added to distilled Water, the carbon soil removal value sought (in mg. of carbon per liter of solution) is obtained by taking the diiference between the converted values of the light transmission of the composite solution or suspension from the nine jars and of the light transmisison of the suspension in the blank jar.
The carbon soil removal values are then reported as a percentage of that of a standard detergent solution used as a reference or control material; viz. by dividing the mg. of carbon removal value of the test material composition by the mg. of carbon removal value for the standard or control detergent solution which is determined concurrently in the same same standard soiled test by 100.
The standard detergent solution used throughout the tests reported herein was a 0.25% soluare poured" through the steel balls and cloth, and multiplying tion of sodium kerylbenzene-sulfonate in distilled water. was prepared The sodium kerylbenzenesulfonate by effecting a Friedel-Crafts condensation of a chlorinated petroleum hydrocarbon distillate (derived from a hydrocarbon distillate having 9-16 carbon atoms and boiling in the range of 150-300 C.) with benzene and thereafter sulfonating the kerylbenzene compound to form the kerylbenzenesulfonic acid, which was subsequently neutralized with caustic soda to form the water-soluble sodium kierylbenzenesulfonate. After the neutralization of the sulfonic acid, suificient sodium sulfate was added so that the final product contained 40% sodium kerylbenzenesulfonate and 60% sodium sulfate.
EFFECT OF POLYOXYPROPYLENE POLY- MER MOLECULAR WEIGHT ON SURFACE ACTIVE PROPERTIES A fundamental feature of this invention resides in the discovery that a polyoxypropylene polymer is sufllciently hydrophobic at a critical minimum molecular weight to serve as the hydrophobic element of surface active agents. The effect and criticalness of the polyoxypropylene polymer molecular weight upon surface active properties is illustrated by Example 2.
EXAMPLE 2 Eight polyoxypropylene polymers were prepared by condensing propylene oxide with propylene glycol following the procedure of Example 1, Part A. The molecular weights of the polyoxypropylene polymers were varied over a wide range and an approximately standard or uniform quantity (viz: 44-48% of the total weight of the product), of ethylene'oxide was added thereto. The procedure of adding the ethylene oxide was the same as that employed in Example 1, Part B. Each of the compounds was then evaluated for carbon soil removal value at 140 F. by the protest run and on the The results are'set TABLE I Molecular Polyoxy- Detergeucy Weight ethylene Carbon Run It Polyoxy- Content, emoval pro ylene Percent of 0.25% at 140 Po ymer Compound F.
The data of the above table are plotted in the attached Fig. 1. It is seen that at polyoxypropylene polymer molecular weights of below 900 the detergency oi the compounds is low, but that at approximately 900 molecular weight there is an inflection in the curve and the carbon soil removal value reaches 100% of standard. Above 900 molecular weight the curve climbs very rapidly to the approximately 225% of standard value at approximately 1100 molecular weight and then levels off, but stays at these high values.
As noted in the above example, all polyoxyalkylene compounds in which the polyoxypropylone polymer has a molecular weight of at least 900 have good detergency at 140 R, which is a conventional temperature used in laundry operations. The products of this invention in which the polyoxypropylene polymer portion has a. molecular weight in excess of 2000 are a preferred embodiment of the invention in that they have exceptionally high detergency in cold water, viz. F. The effect of polyoxy'propylene polymer molecular weight on cold water detergency is illustrated in the following example.
EXAMPLE 3 Five polyoxypropylene polymers of varying molecular weights were prepared by condensing propylene oxide with propylene glycol following the procedure of Example 1, Part A. Ethylene oxide was added to each of the polyxypropylene polymers to prepare compounds having an approximately equivalent quantity of oxyethylene groups (viz: 44-51% of the total weight of the product). Each of the compounds was then evaluated for carbonsoil removal value at the low temperature of 90 F. The results are set forth in Table II below:
TABLE II Molecular Polyoxy- Detergency' Weight ethylene Carbon Soil Run i Polyoxy- Content, Removal propylene Percent of 0.25% at 90 Po ymer Oompoundi F.
l, 48 101 l, 270 44 112 1, 620 51 121 2, s20 44 210 2, 600 47 197 The attached Fig. 2 is based upon the data of the above table. It isseen that at below molecular weights of approximately 2000 the cold water detergency lies within the range of approximately IOU-% of standard. but thatat approximately 2000 molecular weight there is an inflection in the curve and that at all values in excess there of the very high cold water detergency of 200% of standard or more isobtained. These results are particularlly significant inthatthey exceed the values that are obtained with the highest quality soap in much hotter water. of course, the advantages of obtaining high detergency in cold water are obvious.
EFFECT OF POLYOXYETHYLENE CONTENT ON SURFACE ACTIVE PROPERTIES The polyoxyethylene groups must constitute approximately 20-90% of the novel polyoxyalkylene compounds if good detergent values are to be obtained. The criticalness of this range is established by the following example:
EXAMPLE 4 Varying quantities of ethylene oxide were added to 2 polyoxypropylene glycols of 1270 and 2310 molecular weight following the procedure of Example 1, Part B, to prepare compounds having widely varying oxyethylene contents. The resulting compounds were subjected to the carbon soil removal test previously set forth and the results are shown in the following table:
TABLE III Molecular Polyoxy- Detergeney, Weight ethylene Carbon Soil Run Polyoxy- Content, Removal propylene Percent of 0.25% at 140 Polymer Compound F.
l, 270 T 68 1,270 2B 91 1,27) 33 146 1,270 44 202 1, 270 52 225 1, 270 68 20B 1, 270 1 80 141 2,320 as 115 2, 320 37 216 2, 320 44 232 2, 320 52 214 2,320 67 208 2, 320 80 175 When the above data are plotted shaped" curves are obtained which define area of good detergency. It will be seen that the limits of 20-90% encompass the area of good detergency, and wherein the curves rather abruptly change slope from the bordering low detergency values at below 20%, oxyethylene content. The limits of approximately 40-70% oxyethylene content pin point the area or maximum detergency. Essentially the same limits apply when other hydrophilic polyoxyalkylene chains, such as those derived from butadiene dioxide, glycidol, etc. and other alkylene oxides wherein the oxygen/carbon atom ratio is at least 0.5, are contained in the novel polyoxyalkylene compounds.
EFFECT OF Y ON SURFACE ACTIVE. PROPER'ITES As noted heretobefore, the polyoxypropylene is prepared by condensing propylene oxide with a base compound containing a plurality of reactive hydrogen atoms. The function of the base compound is to furnish reactive hydrogen atoms which initiate the polymerization of the propylene oxide and, since the base compound constitutes only a small proportion of the high molecular weight polyoxyalkylene compounds, it ordinarily does not have an influence on the properties thereof. In other words, the particular base compound employed in preparing the novel polyoxyalkylene compounds is not critical so long as it furnishes at least 2 reactive hydrogen atoms, and operable polyoxyalkylene compounds are obtained regardless of the particular base compound employed in the preparation of the polyoxypropylene polymer. Ordinarily it is in Fig. 3, bell the and above 90%,
i. It is sufficiently labile to open the epoxide ring of 1,2 propylene oxide, and
2. It reacts with methyl magnesium iodide to liberate methane in the classical Zerewitinofl reaction (see Niederl and Niederl, Micromethods of Quantitative Organic Analysis, p. 263, John Wiley and Sons, New York city, 1946).
lhe reactive hydrogen atoms which will fulfill the above two conditions are normally activated by being a member of a functional group containin an oxygen atom, e. g. a hydroxyl group, a phenol group, a carboxylic acid group; a. basic nitrogen atom, e. g. an amine group, a hydrazine group, an imine group, an amide group, a guanidine group, a sulionamide group, a urea group, a thiourea group; or a sulfur atom, e. g, a, mercaptan, a, thiophenol, a thiocarboxylic acid, hydrogen sulfide. Alternatively, certain hydrogen atoms may be activated by proximity to carbonyl groups such as those found in cyanoaoetic esters, acetoacetic esters, malonic esters, as is well known in the art. Specific examples or base compounds which may be used in preparing the polyoxypropyleno polymers include ethylene glycol, 1,3 butylene glycol, oxalic acid, glycolic acid, mono-, di-, and triethanolamine. butylamine, aniline, resorcinol, diethylmalonate, etc.
The equivalency of all such base compounds in initiating the condensation of propylene oxide to form the polyoxypropylene polymer is illustrated by the following example.
EXAMPLE 5 Propylene oxide was condensed with, respectively, acetamide, 1,5 pentanediol, glycerine, ethylene diamine, benzene sulfonamide and sucrose to form polyoxypropylene polymers having molecular weights in excess of 900. The general procedure employed was that of Example 1, Part A except for certain minor changes in technique which will be obvious to those skilled in the art. Ethylene oxide was then condensed with the resulting polyoxypropylene polymers to prepare detergent compounds which were evaluated by the method previously set forth. The structure of the resulting compounds and the detergent values thereof are set forth in the following table:
TABLE IV Molecular Polyoxy- Detergency, Weight ethylene Carbon Soil Base Compound (Y) Polyoxy- Content, Removal propylene Percent of 0.25% at P0 ymer Compound F.
While any reactive hydrogen compound containing 2 or more reactive hydrogen atoms may be used in preparing the polyoxypropylene com-- pounds herein disclosed and claimed, the polyoxyalkylene compounds derived from certain specific base compounds have unusual and unsteam and at least one reactive hydrogen atom attached to a nitrogen atom, e. g. ethylene diamine, have exceptionally good cold water detergency and lime soap dispersing powers. Such compounds are more specifically disclosed and claimed in my copending application, Serial No. 349,283, filed April 16, 1953.
CHARACTERISTICS AND APPLICATIONS OF THE NOVEL POLYOXYALKYLENE COM- POUNDS -The compounds of this invention, in addition to the previously described outstanding ability to remove soil from a textile fabric (i. e. detergency is measured by carbon soil removal values) also possess remarkable ability to retain the soil suspended in solution once it is removed. This latter ability is measured by the whiteness retention test, described as follows:
Whiteness retention test procedure Bleached, unfinished, clean Indian Head muslin, county 58 x 7, weight 4.7 oz./sq. yd. (Nashua Manufacturing Company), is cut into swatches measuring 2 x 3 The light reflectance of each side of everyswatch is measured by means of a Hunter Multipurpose Refiectometer equipped with a green flltenusing a standard white backing with a reflectance of 68.8% behind the cloth swatch. The average of such values of each side of each test piece is calculated and recorded. A standard soil suspension is prepared bydiluting 28.55 grams of an aqueous carbon dispersion containing 35% carbon (Aqua Blak B, Binney and Smith 00.) to 1 liter in a volumetric flask of distilled water.
A 0.25% distilled water solution of the detergent compound to be tested is then made up by adding 2.5 grams of the compound to a small amount of distilled water in a 1 liter volumetric flask. The previously prepared'soil suspension is shaken vigorously and 50 ml. then pipetted into the flask containing the detergent. Sui'ltit cient distilled water is then added to this flask to make up to the one-liter mark.
The resultant mixture of detergent and carbon soil suspension is pipetted in 100 ml. portions into each of5 Launder-Ometer jars, each jar containing fifteen 54," stainless steel balls. The jars and contents are brought to a temperature of 140:2 F. in a constant water bath, then placed in the Launder-Ometer and rotated for 5 minutes at 42:2 R. P. M. The Launder-Ometer" is thereafter stopped and without removing the jars from the machine, the lids are opened and two standard cloth swatches, prepared as previously described, are placed in each jar after soaking for exactly 1 minute in distilled water without subsequent draining. The lids are replaced on the jars and the latter are rotated for an additional 30 minutes in the "Launder- Ometer. V'I'he swatches are then removed and .immediatelyrinsedby flowingB liters of distilled.
water continuously through a rinsing flask while shaking, and for a periodtoifi minutes. rimmediately after rinsin the swatches a ieiremov'ed from the rinsing flask and placed on flat clean paper towels. The swatches are pressed on 5 a laundry press set at a temperature of 3283 338 F. After pressing, the reflectance of both sides of each swatch is again measured. by the Hunter Reflectometer andthe average reflectance of all swatches calculated and recorded. The whiteness retention value is then calculatd as follows:
Per cent whiteness retention (W. R.)=
a e. reflectance after soilinglilj!) ave. reflectance before soiling The whiteness retention values are reported herein as a percentage of that determined in the standard detergent solution described under the "Carbon soil removal test procedureyyiz. by dividing the. percent whiteness retention determined in the test material by the percent whiteness retention determined in the standard control detergent solution which is determined concurrently in the same test run and on the same standard test cloth, and multiplying by 100.
The numerical values obtained with several representative compounds of this invention are set forth in the table below:
TABLE V Molecular Weight Polyoxypropylene Polymer I Run Compound Condensation product of propylene oxide and propylene glycol.
Illustrative of the surface tension lowering by the compounds of this invention are the following results:
TABLE VII Molecular Polyoxy- Surface Weight ethylene Tension Run I Polyoxy- Content, 0.1% at propylene Percent of 25 0..
l l, 270 44 35 2 l, 620 81 37 2, 320 37 34 600 47 35 I Condensation product of propylene oxide and propylene glycol.
A desirable characteristic of the polyoxyalkylene compounds of this invention is that both the hydrophobic and the hydrophilic elements thereof can be varied over an extremely wide range of molecular weights. By merely changing the quantity of propylene oxide added to the reactive hydrogen compound it is possible to prepare a wide range of hydrophobic elements that differ from one another in small, finite increments of polyoxypropylene polymer molecular weight. Similarly, varying quantities of ethylene oxide can be added to any of the above-described hydrophobic elements to prepare surface active agents, which differ from each other only in small, finite increments of polyoxyethylene content. By proper selection of reaction conditions, it is possible to vary over a wide range: (1) the hydrophobic polyoxypropylene polymer molecular weight, (2) the hydrophiiic poiyoxyethylene content and (3) the hydrophobic polyoxypropylene polymer molecular weight/hydrophilic polyo-xyethylene content ratio. The facility with which the structure of the surface active agents can be varied is highly advantageous in that surface active agents can be "tailor made to perform specific functions.
In addition to their surface active properties, the polyoxyalkylene compounds of this invention have many other diverse applications in the industrial arts. For example, these compounds have an excellent plasticizing action on a wide range of thermoplastic and thermosetting resins. In this regard, attention is directed to the copending applications of Lester G. Lundsted and J. P. McMahon, Serial No. 231,650, filed June 14, 1951, and Serial No. 259,476, filed December 1. 1951.
In the appended claims, the term cogeneric mixture is used. This is a term that has been coined to designate a series of closely related, touching homologues that are obtained by condensing a plurality of alkylene oxide units with a reactive hydrogen compound (see United States Patent 2,549,438, particularly the section beginning at column 12, line 40).
Also in certain of the claims, organic compounds containing a plurality of reactive hydrogen atoms are defined as having a detergency factor of less than 100. The detergency factor is the measure of the phobic character of any organic compound containing one or more reactive hydrogens and is determined as follows:
Varying quantities of ethylene oxide are added to the reactive hydrogen compound to prepare oxyethylene adducts containing 20:57,], 30:5%. 40:5%, 50:5% and 60-15% oxyethylene content. Distilled water solutions of 0.25% concentration are prepared with each of the adducts. The carbon soil removal value of each adduct is determined at 140 F. following the procedure described by Vaughn and Suter, The Journal of the American Oil Chemists Society, vol. XXVII, No. '7, pp. 249-257. As a control, the carbon soil removal value of an 0.25% distilled water solution of a standard sodium allcvlarylsulfonate detergent is determined concurrently at 140 F. and on the same batch of soiled cloth. The standard detergent is sodium kerylbenzenesulfonate which is prepared by effecting a Friedel-Crafts condensation of a chlorinated petroleum hydrocarbon distillate (derived from a hydrocarbon distillate having 9-16 carbon atoms and boiling in the range of l50-300 C.) with benzene and thereafter sulfonating the kerylbenzene comdetergent-forming, hydro- 14 pound to form the kerylbenzene sulfonic acid, which is subsequently neutralized with caustic soda to fo-rm the water-soluble sodium kerylbenzenesulfonate. After the neutralization of the suli'onic acid, sufficient sodium sulfate is added so that the final product contains 40% sodium kerylbenzenesulfonate and 60% sodium sulfate.
The carbon soil removal values of the oxyethylene adducts are reported on a comparative basis with the standard sodium alkylarylsulfonate detergent being assigned an arbitrary value of 100. The highest carbon soil removal value obtained with the five oxyethylene adducts is then taken as the detergency factor of the reactive hydrogen compound.
What is claimed is:
1. A cogeneric mixture of conjugated polyoxypropylene-polyoxyethylene compounds containing in their structure oxypropylene groups, oxyethylene groups and an organic radical derived from an organic compound containing a plurality of reactive hydrogen atoms; the compounds being characterized in that all of the oxypropylene groups are present in polyoxypropylene chains that are attached to the organic radical at the site of a reactive hydrogen atom thereby constituting a polyoxypropylene polymer; the oxyethylene groups being attached to the polyoxypropylene polymer in polyoxyethylene chains; the average molecular weight of the polyoxyp-ropylene polymers in the mixture being at least 900, as determined by hydroxyl number, and the oxyethylene groups present constituting 20-90%, by weight, of the mixture.
2. A cogeneric mixture of conjugated polyoxypropylene-polyoxyethylene compounds containing in their structure oxypropylene groups, oxyethylene groups and an organic radical derived from an organic compound containing a plurality of reactive hydrogen atoms; the compounds being characterized in that all of the oxypropylene groups are present in polyoxypropylene chains that are attached to the organic radical at the site of a reactive hydrogen atom thereby constituting a polyoxypropylene polymer; the oxyethylene groups being attached to the polyoxypropylene polymer in polyoxyethylene chains; the average molecular weight of the poiyoxypropylene polymers in the mixture being at least 900, as determined by hydroxyl number, and the oxyethylene groups present constituting 40-70 by weight, of the mixture.
3. A cogeneric mixture of conjugated polyoxypropylene-polyoxyethylene compounds containing in their structure oxypropylene groups, oxyethylene groups and an organic radical derived from an organic compound containing a plurality of reactive hydrogen atoms; the compounds being characterized in that all of the oxypropylene groups are present in polyoxypropylene chains that are attached to the organic radical at the site of a reactive hydrogen atom thereby constituting a polyoxypropylene polymer; the oxyethylene groups being attached to the polyoxypropylene polymer in polyoxyethylene chains; the average molecular weight of the polyoxypropylene polymers in the mixture being at least 2000, as determined by hydroxy number, and the oxyethylene groups present constituting 20-90%, by weight, of the mixture.
4. A cogeneric mixture of conjugated polyoxypropylene-polyoxyethylene compounds containing in their structure oxypropylene groups, oxyethylene groups and an organic radical derived from an organic compound containing a plurality constituting a oxypropylene the average propylene polymers in the mixture being at least 2000,'as determined by hydroxyl number, and the oxyethylene by weight, of the mixture.
of at least 0.5 and an the oxypropylpresent in 'polyoxypropylene at the site of a reactive hydrogen atom thereby polyoxypropylene polymer; the oxyethylene groups being attached to the polypolymer in polyoxyethylene chains; molecular weight of the polyoxygroups present constituting 40-70%,
5. A cogeneric mixture of conjugated polyoxyalkylene compounds containing in their structure oxypropylene groups. hydrophilic oxyalkylene groups having an oxygen/carbon atom ratio organic radical derived from an organic compound containing a plurality of reactive hydrogen atoms; the compounds being characterized in that all of the oxypropylene groups are present in polyoxypropylene chains that are attached to the organic radical at the site of a reactive hydrogen atom thereby constituting a polyoxypropylene polymer; the hydrophilic oxyalkylene groups being attached to the polyoxypropylene polymer in polyoxyalkylene chains; the average molecular weight of the polyoxypropylene polymers in the mixture being at least 900, as determined by hydroxyl number, and the hydrophillc oxyalkylene groups present constituting 20-90%, by weight, of the mixture.
6. A cogeneric mixture of conjugated polyoxyalkylene compoundscontaining in their structure oxypropylene groups. hydrophilic oxyalkylene groups having an oxygen/carbon atom ratio of at least 0.5 and an organic radical derived from an organic compound containing a plurality of reactive hydrogen atoms; the compounds being mixture.
7. A cogenerio mixture of conjugated polyoxyalkylene compounds containing in their structure oxypropylene groups, hydrophilic-oxyalkylene groups havingan oxygen/ carbon atom ratio of at least 0.5 and an organicradical derived from an organic compound containing a plurality of reactive hydrogen atoms; the compounds being characterized in that all of the oxypropylene groups are present in polyoxypropylene chains that are attached to the organic radical at the site of a reactive hydrogen atom thereby constituting a polyoxypropylene polymer; the hydrophilic oxyalkylene groups being attached to the polyoxypropylene polymer in polyoxyailwlene chains; the average molecular weight of the polyoxypropylene polymers in the'mixture being at least 2000, as determined by hydroxyl number, and the hydrophilic oxyalkylene groups present constituting 20-90%, by weight, of the mixture.
8. A cogeneric mixture of conjugated polyoxyalkylene compounds containing in their structure oxypropylene groups, hydrophilic oxyalkylene groups having an oxygen/carbon atom ratio of at ieast 0.5 I and an organic radieaiiderived irom reactive hydrogen atoms;
. philicoxyalkylene groups being attached to the t at least 2000, as determined polyoxypropylene polymer in vpolyoxyaikylene chains: the average molecular. weightaofithe polyoxypropylene polymersin thezmixture being by. hydroxyl number, and the hydrophilic oxyalkylenegroups present constituting 40-70%, by weight, ofithe mixture.
9. A cogeneric' mixture of conjugatedcpolyoxypropylene-polyoxyethylene compounds containing in their structure oxypropylene groups, oxyethylene groupsand an organic radicai derived from. an organic compound containing aplurality oi reactive hydrogen atoms and having a detergency factor of less than 100; the compounds being characterized in that all of the oxypropylene groups are present in poiyoxypropylene chains that are attachedtothe organic radical at the site of a reactive hydrogen atom chains; the average molecular weight of the polyoxypropylene polymers in the mixture beingat least 900, as determined by hydroxyl number. and the oxyethylene groups present constituting 20-90%, by weight, of the mixture; said compounds having a carbon soil removal value or at least 100.
10. A cogeneric mixture. of conjugated polyoxyprop-ylene-polyoxyethylene compounds containing in their structure oxypropylene groups,
an organic radicalderived from an organic compound containing a plurality of reactive hydrogen atoms and having a detergency factor of less than 100; the compounds being characterized in that all 01 the oxypropylene groups are present in polyoxypropyl-ene chains that areattached to the organic radical at the site of a reactive hydrogen atom thereby constituting a poiyoxypropylene polymer; theoxyethylene groups being attached'to V the polyoxypro-pylene polymer in polyoxyethyli and the oxyethylene groups present constituting 40-70%, by-weight, of the mixture; said compounds having a carbon soil removal value of at least 100.
11. A cogeneric mixture of oxypropylene-polyoxyethylene compounds containing in their structure oxypropylene groups, oxyethylene groups and an organic radical derived from an organic compound containing a. plurality of reactive hydrogen atoms and having a'detergency factor. of less than 100; the compounds being characterized in that all of the oxypropylen'e groups are present in polyoxypropylene chains that are attached to the organic radical at the'site of a reactive hydrogen atom thereby constituting a polyoxypropylene polymer; the oxyethylene groups being attached to the polyoxypropylene polymer in *poiyoxyethylene chains; the'average molecular weight of the polyoxypropylene polymers in the mixture being at least 2000, as determined by hydroxylnumber, and-the conjugated polyoxyethylene groups present constituting 20-90%, by weight, of the mixture; said compounds havng a carbon soil removal value of at least 100.
12. A cogeneric mixture of conjugated polyoxypropylene-polyoxyethylene compounds containing in their structure oxypropylene groups, oxyethylene groups and an organic radical derived from an organic compound containing a plurality of reactive hydrogen atoms and having a detergency factor of less than 100; the compounds being characterized in that all of the oxypropylene groups are present in polyoxypropylene chains that are attached to the organic radical at the site of a reactive hydrogen atom thereby constituting a polyoxypropylene polymer; the oxyethylene groups being attached to the polyoxypropylene polymer in polyoxyethylene chains; the average molecular weight of the polyoxypropylene polymers in the mixture being at least 2000, as determined by hydroxyl number, and the oxyethylene groups present constituting 40-70%, by weight, of the mixture; said compounds having a carbon soil removal value of at least 100.
13. A cogeneric mixture of conjugated polyoxypropylene-polyoxyethylene compounds containing in their structure oxypropylene groups. oxyethylene groups and an organic radical derived from an organic compound containing a plurality of reactive hydrogen atoms, said compound having a molecular weight of less than 200, the reactive hydrogen atoms of said organic compound being members of functional groups containing an element selected from the group consisting of oxygen, sulfur and nitrogen; the compounds being characterized in that all of the oxypropylene groups are present in polyoxypropylene chains that are attached to the organic radical at the site of a reactive hydrogen atom thereby constituting a polyoxypropylene polymer; the oxyethylene groups being attached to the polyoxypropylene polymer in polyoxyethylene chains; the average molecular weight of the polyoxypropylene polymers in the mixture being at least 900, as determined by hydroxyl number, and. the oxyethylene groups present constituting 20-90%, by weight, of the mixture: said. compounds having a carbon soil removal value of at least 100.
14. A cogeneric mixture of conjugated polyoxypropylene-polyoxyethylene compounds containing in their structure oxypropylene groups. oxyethylene groups and an organic radical derived from a polyhydric alcohol having a molecular weight of less than 200; the com pounds being characterized in that all of the oxypropylene groups are present in polyoxypropylene chains that are attached to the organic radical at the site of a reactive hydrogen atom thereby constituting a polyoxypropylene polymer; the oxyethylene groups being attached to the polyoxypropylene polymer in polyoxyethylene chains; the average molecular weight of the polyoxypropylene polymers in the mixture being at least 900, as determined by hydroxyl number. and the oxyethylene groups present constituting 20-90%, by weight, of the mixture.
15. A cogeneric mixture of conjugated poly- 18 oxypropylene-polyoxyethylene compounds containing in their structure oxvpropylene groups, oxyethylene groups and an organic radical derived from a carboxylic acid amide having a molecular weight of less than 200; the compounds being characterized ln that all of the oxyp-ropylene groups are present in polyoxypropylene chains that are attached to the organic radical at the site of a reactive hydrogen atom. thereby constituting a polyoxypropylene polymer; the oxyethylene groups being attached to the polyoxypropylene polymer in polyoxyethylene chains; the average molecular weight of the polyoxypropylene polymers in the mixture being at least 900, as determined by hydroxyl number, and the oxyethylene groups present constituting 29-90%, by weight, of the mixture.
16. A cogeneric mixture of conjugated polyoxypropylene-polyoxyethylene compounds containing in their structure oxypropylene groups, oxyethylene groups and an organic radical derived from an arylsulfonamide having a plurality of reactive hydrogen atoms and a molecular weight of less than 200; the compounds being characterized in that all of the oxypropylene groups are present in polyoxypropylene chains that are attached to the organic radical at the site of a reactive hydrogen atom thereby constituting a polyoxypropylene polymer; the oxyethylene groups being attached to the polyoxypropylene polymer in polyoxyethylene chains; the average molecular weight of the polyoxypropylene polymers in the mixture being at least 900, as determined by hydroxyl number, and the oxyethylene groups present constituting 20-90%, by weight, of the mixture.
17. A cogeneric mixture of conjugated polyoxypropylene-polyoxyethylene compounds containing in their structure oxypropylene groups, oxyethylene groups and an organic radical derived from a polybasic carboxylic acid having a molecular weight of less than 200; the compounds being characterized in that all of the oxypropylene groups are present in polyoxypropylene chains that are attached to the organic radical at the site of a reactive hydrogen atom thereby constituting a polyoxypropylene polymer; the oxyethylene groups being attached to the polyoxypropylene polymer in polyoxyethylene chains; the average molecular weight of the polyoxypropylene polymers in the mixture being at least 900, as determined by hydroxyl number, and the oxyethylene groups present constituting 20-90%, by weight, of the mixture.
18. Compounds having improved detergent properties, according to the formula:
where 3 equals at least 15; and (C2H4O)a:+.1:' equals 20-90%, of the total weight of the compound.
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,549,439 De Groote et a1 Apr. 17, 1951 2,552,529 De Groote May 15, 1951
Claims (1)
17. A COGENERIC MIXTURE OF CONJUGATED POLUOXYPROPYLENE-POLYOXYETHYLENE COMPOUND CONTAINING IN THEIR STRUCTURE OXYPROPYLENE GROUPS, OXYETHYLENE GROUPS AND AN ORGANIC RADICAL DERIVED FROM A POLYBASIC CARBOXYLIC ACID HAVING A MOLECULAR WEIGHT OF LESS THAN 200; THE COMPOUNDS BEING CHARACTERIZED IN THAT ALL OF THE OXYPROPULENE GROUPS ARE PRESENT IN POLYOXYPROPYLENE CHAINS THAT ARE ATTACHED TO THE ORGANIC RADICAL AT THE SITE OF A REACTIVE HYDROGEN ATOM THEREBY CONSTITUTING A POLYOXYPROPYLENE POLYMER; THE
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US386945A US2674619A (en) | 1953-10-19 | 1953-10-19 | Polyoxyalkylene compounds |
US705730A US2979528A (en) | 1953-10-19 | 1957-12-30 | Nitrogen-containing polyoxyalkylene detergent compositions |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US386945A US2674619A (en) | 1953-10-19 | 1953-10-19 | Polyoxyalkylene compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
US2674619A true US2674619A (en) | 1954-04-06 |
Family
ID=23527760
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US386945A Expired - Lifetime US2674619A (en) | 1953-10-19 | 1953-10-19 | Polyoxyalkylene compounds |
Country Status (1)
Country | Link |
---|---|
US (1) | US2674619A (en) |
Cited By (374)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2727867A (en) * | 1951-10-24 | 1955-12-20 | Dearborn Chemicals Co | Method of inhibiting foam formation in steam generating systems |
US2759867A (en) * | 1953-11-27 | 1956-08-21 | Dow Chemical Co | Cyclohexyl-phenol-alkylene-oxide repellent and method |
US2771450A (en) * | 1955-04-04 | 1956-11-20 | Petrolite Corp | Process for breaking emulsions |
US2786080A (en) * | 1953-11-25 | 1957-03-19 | Wyandotte Chemicals Corp | Stabilized polyoxyalkylene compositions |
US2786796A (en) * | 1953-11-27 | 1957-03-26 | Dow Chemical Co | Method of repelling flies with dibutylphenyl monoether polyglycols |
US2802024A (en) * | 1953-12-17 | 1957-08-06 | Exxon Research Engineering Co | Diesters of oxo glycols |
US2802736A (en) * | 1954-10-29 | 1957-08-13 | Dow Chemical Co | Poultry feed |
US2805169A (en) * | 1955-07-18 | 1957-09-03 | Rayonier Inc | High-alpha cellulose |
US2805949A (en) * | 1954-10-29 | 1957-09-10 | Dow Chemical Co | Poultry feed |
US2814613A (en) * | 1952-12-31 | 1957-11-26 | British Petroleum Co | Production and/or separation of nonionic surface active agents |
US2828345A (en) * | 1955-04-27 | 1958-03-25 | Dow Chemical Co | Hydroxypolyoxyethylene diethers of polyoxybutylene glycols |
US2831034A (en) * | 1953-12-07 | 1958-04-15 | Dow Chemical Co | Polyoxyalkylene glycol ethers of glycerine |
US2839476A (en) * | 1955-02-07 | 1958-06-17 | Petrolite Corp | Certain non-ionic surfactants and method of making same |
US2839477A (en) * | 1958-06-17 | Table ii | ||
US2847384A (en) * | 1954-10-19 | 1958-08-12 | Wyandotte Chemicals Corp | Descalant composition and use |
US2861887A (en) * | 1954-10-29 | 1958-11-25 | Dow Chemical Co | Poultry feed |
US2870019A (en) * | 1954-09-16 | 1959-01-20 | Upjohn Co | Therapeutic composition |
US2875128A (en) * | 1953-12-07 | 1959-02-24 | Visco Products Co | Pesticide emulsions containing an oxyethylated oxypropylated glycerine |
US2876263A (en) * | 1952-12-31 | 1959-03-03 | Universal Oil Prod Co | Polyoxyalkylene cyclic hydrocarbon substituted amines and their ammonium salt derivatives |
US2882171A (en) * | 1956-11-14 | 1959-04-14 | Dearborn Chemicals Co | Corrosion inhibiting composition and method |
US2897163A (en) * | 1956-07-09 | 1959-07-28 | Union Carbide Corp | Production of polymeric materials from polyoxyalkylene polyols and butadiene diepoxide |
US2898334A (en) * | 1955-07-26 | 1959-08-04 | Rayonier Inc | Cellulose slurry-steeping |
US2917468A (en) * | 1956-01-18 | 1959-12-15 | Bayer Ag | Surface active polymeric trimethylene oxide derivatives with polyether sidechains, and process for producing same |
US2921920A (en) * | 1956-07-03 | 1960-01-19 | Union Carbide Corp | Polyethylene telomer-polyalkylene oxide block copolymer and method of preparing same |
US2923686A (en) * | 1955-05-23 | 1960-02-02 | Dow Chemical Co | Glycol antifreeze mixtures |
US2923690A (en) * | 1957-03-28 | 1960-02-02 | Jefferson Chem Co Inc | Preparation of high molecular weight polyethylene glycols |
US2932670A (en) * | 1957-09-16 | 1960-04-12 | Monsanto Chemicals | Derivatives of glycerol 1, 3-dialkyl ethers and their preparation |
US2941892A (en) * | 1955-01-31 | 1960-06-21 | Atlas Powder Co | Spinning of viscose |
US2948757A (en) * | 1953-12-07 | 1960-08-09 | Dow Chemical Co | Trihydroxy polyoxyalkylene ethers of glycerol |
US2950272A (en) * | 1957-03-25 | 1960-08-23 | Visco Products Co | Polyoxyalkylene esters of tall oil rosin acids |
US2977283A (en) * | 1956-04-30 | 1961-03-28 | Upjohn Co | Therapeutic intravenous fat compositions |
US2979528A (en) * | 1953-10-19 | 1961-04-11 | Wyandotte Chemicals Corp | Nitrogen-containing polyoxyalkylene detergent compositions |
US2983684A (en) * | 1956-11-28 | 1961-05-09 | Wyandotte Chemicals Corp | Soap composition containing lime soap dispersant |
US2990396A (en) * | 1955-10-14 | 1961-06-27 | Union Carbide Corp | Production of polymeric materials from polyoxyalkylene polyols and organic polyepoxy compounds |
US2999045A (en) * | 1953-07-22 | 1961-09-05 | Rayonier Inc | Deresination of wood pulp |
US3014073A (en) * | 1956-04-23 | 1961-12-19 | John A Gallaghan | 1, 3-bis(nitroguanidino)-2-nitroxypropane, 1, 3-bis(guanidinium)-2-hydroxy propane and the preparation thereof |
US3014810A (en) * | 1958-09-08 | 1961-12-26 | Armour & Company Of Delaware | Pigment composition and method of manufacture |
US3016305A (en) * | 1956-05-10 | 1962-01-09 | Kunstzijdespinnerij Nyma Nv | Manufacture of thick-skinned or allskin shaped articles from viscose |
US3020176A (en) * | 1958-03-13 | 1962-02-06 | Mead Corp | Cast coated paper and method of making the same |
US3022335A (en) * | 1955-03-30 | 1962-02-20 | Wyandotte Chemicals Corp | Surface active polyoxyalkylene compounds having a plurality of heteric polyoxypropylene-polyoxyethylene chains |
DE1126140B (en) * | 1959-07-31 | 1962-03-22 | Boehme Fettchemie Gmbh | Process for the production of alkylene oxide addition products with low foaming capacity |
US3029183A (en) * | 1959-05-18 | 1962-04-10 | West Laboratories Inc | Germicidal iodine compositions |
US3029216A (en) * | 1958-08-11 | 1962-04-10 | Union Carbide Corp | Block copolymer of dissimilar 1, 2-alkylene oxides and process for preparing the same |
US3030197A (en) * | 1960-11-22 | 1962-04-17 | Petrolite Corp | Thermally stable distillate fuels |
DE1128147B (en) * | 1959-08-01 | 1962-04-19 | Hoechst Ag | Process for the oxaethylation of compounds containing carboxyl groups |
US3031510A (en) * | 1957-10-01 | 1962-04-24 | Economics Lab | Nonionic surface active agent |
US3031320A (en) * | 1955-08-22 | 1962-04-24 | Atlas Chem Ind | Spinning of viscose |
US3036118A (en) * | 1957-09-11 | 1962-05-22 | Wyandotte Chemicals Corp | Mixtures of novel conjugated polyoxyethylene-polyoxypropylene compounds |
US3077375A (en) * | 1955-08-22 | 1963-02-12 | Atlas Chem Ind | Spinning of viscose |
DE1149907B (en) * | 1959-02-25 | 1963-06-06 | Basf Ag | Process for the production of higher molecular weight alcohols which contain the grouping -CH-CH-O- |
US3101374A (en) * | 1958-08-19 | 1963-08-20 | Wyandotte Chemicals Corp | Polyoxyalkylene surface active agents having heteric polyoxyethylene solubilizing chains |
US3110737A (en) * | 1958-09-15 | 1963-11-12 | Petrolite Corp | Certain oxyalkylated polyols |
US3110736A (en) * | 1958-09-15 | 1963-11-12 | Petrolite Corp | Certain oxyalkylated polyols |
US3112281A (en) * | 1957-09-17 | 1963-11-26 | Wyandotte Chemicals Corp | Polyurethane foams and process for preparing same |
US3118000A (en) * | 1959-08-10 | 1964-01-14 | Rohm & Haas | Polyoxyalkylene surface-active agents |
US3117998A (en) * | 1959-04-14 | 1964-01-14 | Allied Chem | Propylene oxide polyethers |
US3117999A (en) * | 1959-08-10 | 1964-01-14 | Rohm & Haas | Tert-carbinamine polyoxyalkylene surface-active agents |
DE1161683B (en) * | 1958-08-15 | 1964-01-23 | Ici Ltd | Process for the production of polyurethane foams |
US3121750A (en) * | 1954-06-10 | 1964-02-18 | Petrolite Corp | Oxyalkylated tris(hydroxymethyl)-aminomethanes |
US3121749A (en) * | 1954-06-10 | 1964-02-18 | Petrolite Corp | Oxyalkylated tris(hydroxymethyl)-aminomethanes |
DE1164670B (en) * | 1957-02-22 | 1964-03-05 | Council Scient Ind Res | Process for the preparation of surface-active compounds from compounds containing active hydrogen atoms and alkylene oxides |
US3128314A (en) * | 1958-05-08 | 1964-04-07 | Petrolite Corp | Oxyalkylated condensates |
US3133905A (en) * | 1960-05-23 | 1964-05-19 | Goodyear Tire & Rubber | Polyhydroxyl terminated polyethers |
DE1176358B (en) * | 1959-08-12 | 1964-08-20 | Pittsburgh Plate Glass Co | Process for the production of optionally foamed polyurethanes |
US3146272A (en) * | 1959-04-02 | 1964-08-25 | Dow Chemical Co | Antioxidants for glycol derivatives |
US3154498A (en) * | 1960-12-06 | 1964-10-27 | Calgon Corp | Water treating composition |
US3156574A (en) * | 1959-09-09 | 1964-11-10 | Ici Ltd | Process of incorporating aqueous pigment composition in viscose |
US3161682A (en) * | 1960-04-28 | 1964-12-15 | Jefferson Chem Co Inc | Method for preparing polyoxyalkylene primary amines |
US3162601A (en) * | 1962-01-10 | 1964-12-22 | Pan American Petroleum Corp | Paraffin removal and prevention |
US3167517A (en) * | 1960-08-11 | 1965-01-26 | American Cyanamid Co | Dyeing assistant and leveling compositions |
US3168576A (en) * | 1959-12-10 | 1965-02-02 | Sun Oil Co | Purification of alkyl phenol oxidation inhibitors |
US3189653A (en) * | 1962-08-20 | 1965-06-15 | Grace W R & Co | Mono hydrazinium hydroxypolyalkoxy-alkylalkylene-diamines |
US3207791A (en) * | 1962-09-19 | 1965-09-21 | Atlantic Refining Co | Polyalkoxyhydroxyamines |
US3222300A (en) * | 1957-11-09 | 1965-12-07 | Bayer Ag | Polyurethane plastics from a polyalkylene ether bearing solely terminal hydroxyl groups |
DE1206877B (en) * | 1963-03-12 | 1965-12-16 | Richard Huttenlocher Dr Ing | Process for the production of surface-active, biodegradable ethers of sugars or polyhydric aliphatic alcohols |
US3231619A (en) * | 1959-12-18 | 1966-01-25 | Jefferson Chem Co Inc | Basic primary amino polyether compositions |
US3232779A (en) * | 1955-01-20 | 1966-02-01 | Mo Och Domsjoe Ab | Methods of producing regenerated cellulose |
US3250719A (en) * | 1963-09-30 | 1966-05-10 | Wyandotte Chemicals Corp | Foaming detergent compositions |
US3256211A (en) * | 1963-06-05 | 1966-06-14 | Union Carbide Corp | Interpolymer of ethylene oxide and at least one different 1, 2-alkylene oxide |
US3262809A (en) * | 1962-06-29 | 1966-07-26 | Owens Corning Fiberglass Corp | Size composition for glass, and treated glass structures and method for manufacturing same |
US3272899A (en) * | 1960-12-06 | 1966-09-13 | Hagan Chemicals & Controls Inc | Process for producing a solid rinse block |
US3294540A (en) * | 1963-12-17 | 1966-12-27 | Eastman Kodak Co | Lith-type emulsions with block co-polymers |
US3314891A (en) * | 1964-05-27 | 1967-04-18 | Wyandotte Chemicals Corp | Low foaming detergent |
US3337463A (en) * | 1963-10-18 | 1967-08-22 | Wyandotte Chemicals Corp | Foaming detergent compositions |
US3341456A (en) * | 1964-06-11 | 1967-09-12 | Olin Mathieson | Water-based hydraulic fluid |
US3377130A (en) * | 1960-08-11 | 1968-04-09 | American Cyanamid Co | Dyed nitrogenous fibers and anionic dye composition therefor |
US3380925A (en) * | 1962-05-17 | 1968-04-30 | Henkel & Cie Gmbh | Polyglycol ethers suitable for detergent preparations |
US3383326A (en) * | 1964-03-06 | 1968-05-14 | Nalco Chemical Co | Compositions and processes for breaking petroleum emulsions |
US3406236A (en) * | 1964-01-15 | 1968-10-15 | Bayer Ag | Method of molding articles utilizing mold coated with release agent comprising polysiloxane-polyoxyalkylene mixture |
US3406208A (en) * | 1962-05-17 | 1968-10-15 | Henkel & Compagnie G M B H | Polyglycol ethers suitable for detergent preparations, and process for preparing the same |
US3418218A (en) * | 1966-03-11 | 1968-12-24 | Chrysler Corp | Sealing of aluminum surfaces |
US3438907A (en) * | 1965-07-26 | 1969-04-15 | Wyandotte Chemicals Corp | Iodine-containing nonionic surfactant compositions |
US3450502A (en) * | 1967-09-25 | 1969-06-17 | Wyandotte Chemicals Corp | Method of operating heart-lung apparatus |
US3536497A (en) * | 1967-12-21 | 1970-10-27 | Wyandotte Chemicals Corp | Method for retarding staling of baked goods |
US3624208A (en) * | 1967-01-20 | 1971-11-30 | Wyandotte Chemicals Corp | Floating bath oil composition |
US3669911A (en) * | 1969-09-26 | 1972-06-13 | Dow Chemical Co | Process and compositions for making porous low density thermoset resins from water-in-resin emulsions |
US3681456A (en) * | 1969-05-26 | 1972-08-01 | Jefferson Chem Co Inc | Thiourea compound |
US3864315A (en) * | 1970-03-23 | 1975-02-04 | Kuraray Co | Fiber-forming polyester composition including a polyalkylene ether |
US3867533A (en) * | 1968-12-20 | 1975-02-18 | Basf Wyandotte Corp | Preparation of aqueous gel compositions containing a water-insoluble organic ingredient |
US3866800A (en) * | 1969-02-12 | 1975-02-18 | Alberto Culver Co | Non-pressurized package containing self-heating products |
US3900518A (en) * | 1967-10-20 | 1975-08-19 | Gen Tire & Rubber Co | Hydroxyl or thiol terminated telomeric ethers |
US3925241A (en) * | 1966-09-19 | 1975-12-09 | Basf Wyandotte Corp | Amphoteric surfactant gels |
US3931336A (en) * | 1972-08-22 | 1976-01-06 | Badische Anilin- & Soda-Fabrik Aktiengesellschaft | Production of oxyalkylated α-hydroxy acetylenic compounds |
US3932355A (en) * | 1974-06-19 | 1976-01-13 | E. I. Du Pont De Nemours And Company | Preparation of sol chloroprene polymers |
US3939094A (en) * | 1973-11-30 | 1976-02-17 | New England Nuclear Corporation | Compositions and process for liquid scintillation counting |
US4025456A (en) * | 1974-09-20 | 1977-05-24 | Union Carbide Corporation | Polysiloxane-polyoxyalkylene block copolymers |
US4039576A (en) * | 1972-03-28 | 1977-08-02 | Ciba-Geigy Corporation | Process for the manufacture of alkoxylated N-methylol ureas |
US4043752A (en) * | 1975-12-17 | 1977-08-23 | E. I. Du Pont De Nemours And Company | Phenylazoaminophenylpyrazole acid dye solutions containing two nonionic surfactants |
US4076497A (en) * | 1975-02-01 | 1978-02-28 | Basf Aktiengesellschaft | Continuous dyeing of polyester fibers and cellulose fibers |
US4082703A (en) * | 1975-04-07 | 1978-04-04 | Union Carbide Corporation | Polyurethane prepolymers, rebonded polyurethane foam and methods of forming the same |
US4102795A (en) * | 1976-04-30 | 1978-07-25 | Kao Soap Co., Ltd. | Softener composition for fabrics or hair |
US4110227A (en) * | 1977-09-19 | 1978-08-29 | Basf Wyandotte Corporation | Oxidation stable polyoxyalkylene fiber lubricants |
US4111865A (en) * | 1974-11-13 | 1978-09-05 | Union Carbide Corporation | Polymer/polyols and polyurethane forms and elastomers therefrom |
US4117031A (en) * | 1974-09-26 | 1978-09-26 | Hoechst Aktiengesellschaft | Crude oil demulsifiers |
US4119502A (en) * | 1977-08-17 | 1978-10-10 | M&T Chemicals Inc. | Acid zinc electroplating process and composition |
US4130477A (en) * | 1976-12-27 | 1978-12-19 | The Dow Chemical Company | Froth flotation process |
US4151269A (en) * | 1977-04-11 | 1979-04-24 | Shiseido Co., Ltd. | Hairdressing preparation |
US4172173A (en) * | 1976-06-30 | 1979-10-23 | Celanese Corporation | Ethylene-vinyl acetate polymer binders for non-woven fabrics |
US4183903A (en) * | 1978-08-02 | 1980-01-15 | Exxon Research & Engineering Co. | Method of removing carbon dioxide from gases utilizing an alkaline absorption solution containing a cyclic urea anti-foaming agent |
US4208385A (en) * | 1978-08-04 | 1980-06-17 | Exxon Research & Engineering Co. | Process for defoaming acid gas scrubbing solutions and defoaming solutions |
US4248935A (en) * | 1978-08-21 | 1981-02-03 | Ppg Industries, Inc. | Storage stable polyolefin compatible non-crosslinking size for fiber glass strands |
US4252540A (en) * | 1978-10-12 | 1981-02-24 | Kao Soap Co., Ltd. | Stabilizer for mixture fuels |
US4252969A (en) * | 1979-09-27 | 1981-02-24 | National Distillers And Chemical Corp. | Process for regulating particle size of finely divided thermoplastic resins |
US4265774A (en) * | 1976-10-29 | 1981-05-05 | Basf Wyandotte Corporation | Oxyalkylated polyglycerols and water-based lubricants prepared therefrom |
US4276054A (en) * | 1979-12-19 | 1981-06-30 | Basf Wyandotte Corporation | Coal-oil slurries containing a surfactant |
US4288639A (en) * | 1979-10-22 | 1981-09-08 | Basf Wyandotte Corporation | Alpha-olefin oxide-modified liquid polyether thickeners |
US4288232A (en) * | 1979-12-19 | 1981-09-08 | Basf Wyandotte Corporation | Ester containing fuel composition |
US4293428A (en) * | 1978-01-18 | 1981-10-06 | Exxon Production Research Company | Propoxylated ethoxylated surfactants and method of recovering oil therewith |
US4310436A (en) * | 1979-10-22 | 1982-01-12 | Basf Wyandotte | Polyether-based thickeners with additives for increased efficiency in aqueous systems |
US4312973A (en) * | 1978-08-10 | 1982-01-26 | Union Carbide Corporation | Polyurethane elastomers prepared from polyol or polymer/polyol-chain extender mixtures |
US4312775A (en) * | 1979-10-22 | 1982-01-26 | Basf Wyandotte Corporation | Polyether thickeners for aqueous systems containing additives for increased thickening efficiency |
US4317940A (en) * | 1980-12-23 | 1982-03-02 | Olin Corporation | Biodegradable surfactants |
US4323467A (en) * | 1980-11-24 | 1982-04-06 | Syntex (U.S.A.) Inc. | Contact lens cleaning, storing and wetting solutions |
EP0051878A1 (en) * | 1980-11-12 | 1982-05-19 | Union Carbide Corporation | Low-foaming nonionic surfactants |
US4332692A (en) * | 1979-02-28 | 1982-06-01 | The Procter & Gamble Company | Laundering with a nonionic detergent system at a temperature between the cloud point and the phase coalescence temperatures |
US4333488A (en) * | 1980-09-08 | 1982-06-08 | Conoco Inc. | Method of transporting viscous hydrocarbons |
DE3144371A1 (en) * | 1980-11-13 | 1982-06-09 | Basf Ag, 6700 Ludwigshafen | Low-foam and biodegradable alkoxylation products whose end groups are blocked by glycerol ether radicals, a process for their preparation and their use as surfactants in detergents and cleaning agents |
US4340766A (en) * | 1980-02-14 | 1982-07-20 | Basf Aktiengesellschaft | Dishwashing agents and cleaning agents containing oxybutylated higher alcohol/ethylene oxide adducts as low-foaming surfactants |
US4340382A (en) * | 1980-12-16 | 1982-07-20 | Union Carbide Corporation | Method for treating and processing textile materials |
US4343716A (en) * | 1978-08-02 | 1982-08-10 | Exxon Research & Engineering Co. | 1-Secondary or 1-tertiary alkyl or cycloalkyl-hexahydro-2-pyrimidinones and 1-secondary or 1-tertiary alkyl or 1-cycloalkyl-2-imidazolidinones and their use as antifoaming agents |
US4351753A (en) * | 1980-10-24 | 1982-09-28 | Basf Wyandotte Corporation | Liquified normally solid polyoxyalkylene block copolymers |
US4358501A (en) * | 1978-08-14 | 1982-11-09 | Ppg Industries, Inc. | Storage stable polyolefin compatible size for fiber glass strands |
US4358293A (en) * | 1981-01-29 | 1982-11-09 | Gulf & Western Manufacturing Co. | Coal-aqueous mixtures |
US4395351A (en) * | 1979-10-22 | 1983-07-26 | Camp Ronald L | Polyether-based thickeners with additives for increased efficiency in aqueous systems |
US4406798A (en) * | 1981-08-24 | 1983-09-27 | Pfizer Inc. | Surfactant enhanced injectivity of xanthan mobility control solutions for tertiary oil recovery |
US4411810A (en) * | 1981-11-06 | 1983-10-25 | Basf Wyandotte Corporation | Low-foaming nonionic surfactant for machine dishwashing detergent |
US4413085A (en) * | 1978-08-21 | 1983-11-01 | Ppg Industries, Inc. | Storage stable polyolefin compatible non-crosslinking size for fiber glass strands |
JPS58223430A (en) * | 1983-04-13 | 1983-12-26 | Kao Corp | Aqueous dispersion stabilizer of fine coal powder |
US4428860A (en) | 1979-10-22 | 1984-01-31 | Basf Wyandotte Corporation | Polyether thickeners for aqueous systems containing additives for increased thickening efficiency |
US4464193A (en) * | 1980-02-19 | 1984-08-07 | Basf Wyandotte Corporation | Anionic biocide emulsions in aqueous solutions of strongly ionizable salts |
US4469606A (en) * | 1982-07-26 | 1984-09-04 | Ciba-Geigy Corporation | Stabilization systems for fiber finishes |
US4483741A (en) * | 1982-08-10 | 1984-11-20 | Economics Laboratory, Inc. | Low-foaming, pH sensitive, alkylamine polyether surface active agents and methods for using |
US4506018A (en) * | 1982-12-30 | 1985-03-19 | Becton, Dickinson And Company | Blood diluent |
US4534959A (en) * | 1983-08-22 | 1985-08-13 | Basf Wyandotte Corporation | Aerosol gel |
US4534958A (en) * | 1983-07-13 | 1985-08-13 | Basf Wyandotte Corporation | Aerosol gel |
US4594366A (en) * | 1983-06-29 | 1986-06-10 | Union Carbide Corporation | Connected branched polyols and polyurethanes based thereon |
US4601836A (en) * | 1981-10-13 | 1986-07-22 | Jones L W | Phosphate ester/alcohol micellar solutions in well acidizing |
US4605773A (en) * | 1982-08-10 | 1986-08-12 | Diamond Shamrock Chemicals Company | Low-foaming, pH sensitive, alkylamine polyether surface active agents and methods for using |
US4606918A (en) * | 1983-08-22 | 1986-08-19 | Syntex (U.S.A.) Inc. | Polyoxypropylene-polyoxyethylene block polymer based adjuvants |
US4618442A (en) * | 1985-10-07 | 1986-10-21 | Geary Robert J | Plant cryoprotection |
US4661275A (en) * | 1985-07-29 | 1987-04-28 | The Lubrizol Corporation | Water-based functional fluid thickening combinations of surfactants and hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products |
US4664834A (en) * | 1985-07-29 | 1987-05-12 | The Lubrizol Corporation | Hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products, and aqueous systems containing same |
US4665239A (en) * | 1979-10-22 | 1987-05-12 | Basf Corporation | Polyethers modified with alpha olefin oxides |
US4676916A (en) * | 1985-12-02 | 1987-06-30 | Basf Corporation | Acidizing concentrates for oil well acidizing systems |
US4726909A (en) * | 1985-12-23 | 1988-02-23 | Basf Corporation | Low odor surfactant |
WO1988001272A2 (en) | 1986-08-14 | 1988-02-25 | The Lubrizol Corporation | Borated amine salts of monothiophosphoric acids |
WO1988001873A1 (en) * | 1986-09-22 | 1988-03-24 | Emory University | Vaccine and method of preparation |
EP0268920A1 (en) * | 1986-11-21 | 1988-06-01 | BASF Corporation | Process for preparing capped polyoxyalkylene block polyethers |
US4836951A (en) * | 1986-02-19 | 1989-06-06 | Union Carbide Corporation | Random polyether foam control agents |
US4859358A (en) * | 1988-06-09 | 1989-08-22 | The Procter & Gamble Company | Liquid automatic dishwashing compositions containing metal salts of hydroxy fatty acids providing silver protection |
JPH01503458A (en) * | 1987-02-20 | 1989-11-22 | エモリ ユニバーシティ | anti-infective compounds |
US4886609A (en) * | 1987-10-09 | 1989-12-12 | Gaf Corporation | Method for stimulation of oil and gas wells |
US4933179A (en) * | 1983-08-22 | 1990-06-12 | Syntex (U.S.A.) Inc. | Feline leukemia virus antigen vaccines |
US4937070A (en) * | 1986-05-15 | 1990-06-26 | Emory University | Methods and compositions for treatment of pathological hydrophobic interactions in biological fluids |
US4965019A (en) * | 1988-01-11 | 1990-10-23 | Henkel Kommanditgesellschaft Auf Aktien | Use of selected end-group closed fatty alcohol ethoxylates for low-foam, cold-sprayable cleaning agents |
US4988452A (en) * | 1988-06-09 | 1991-01-29 | The Procter & Gamble Company | Liquid automatic dishwashing detergent compositions containing bleach-stable nonionic surfactant |
US4997644A (en) * | 1986-05-15 | 1991-03-05 | Emory University | Method of treating adult respiratory distress syndrome |
US5017370A (en) * | 1986-05-15 | 1991-05-21 | Emory University | Improved method of performing angioplasty procedures |
US5026734A (en) * | 1989-01-12 | 1991-06-25 | Browning Henry A | Method of controlling fungus, mites, worms, termites, nematodes and other insects |
US5028599A (en) * | 1986-05-15 | 1991-07-02 | Emory University | Method of treating mycardial damage |
US5028353A (en) * | 1988-10-07 | 1991-07-02 | Colgate-Palmolive Company | Process of preparing a combination detergent and soap bar with enhanced mildness |
US5030448A (en) * | 1986-05-15 | 1991-07-09 | Emory University | Method of delivering drugs to damaged or diseased tissue |
US5032394A (en) * | 1986-05-15 | 1991-07-16 | Emory University | Method of treating burns |
EP0439755A2 (en) | 1990-01-29 | 1991-08-07 | BASF Corporation | Process for preparing graft polyols and the polyols prepared thereby |
US5039520A (en) * | 1986-05-15 | 1991-08-13 | Emory University | Plasma extender |
US5041288A (en) * | 1986-05-15 | 1991-08-20 | Emory University | Method of treating tissue damaged by reperfusion injury |
US5047236A (en) * | 1986-05-15 | 1991-09-10 | Emory University | Method of treating stroke |
US5064583A (en) * | 1989-08-01 | 1991-11-12 | Zycon Corporation | Method for applying mold release coating to separator plates for molding printed circuit boards |
US5071649A (en) * | 1986-05-15 | 1991-12-10 | Emory University | Method of preventing blockage in catheters |
US5078995A (en) * | 1986-05-15 | 1992-01-07 | Emory University | Fibrionolytic composition |
US5080894A (en) * | 1986-05-15 | 1992-01-14 | Emory University | Method and composition for reducing tissue damage |
US5089260A (en) * | 1986-05-15 | 1992-02-18 | Emory University | Method of treating ischemic tissue |
US5103062A (en) * | 1987-04-10 | 1992-04-07 | Texaco Inc. | Modified normally liquid, water-soluble polyoxyalkylene polyamines |
US5124389A (en) * | 1986-03-17 | 1992-06-23 | Mente Donald C | Thickening aqueous systems |
US5126068A (en) * | 1989-05-05 | 1992-06-30 | Burke John J | Hard surface cleaning composition containing polyacrylate copolymers as performance boosters |
US5130043A (en) * | 1988-06-09 | 1992-07-14 | The Procter & Gamble Company | Liquid automatic dishwashing compositions having enhanced stability |
US5135751A (en) * | 1988-11-16 | 1992-08-04 | Mediventures Incorporated | Composition for reducing postsurgical adhesions |
US5151093A (en) * | 1990-10-29 | 1992-09-29 | Alza Corporation | Osmotically driven syringe with programmable agent delivery |
US5152979A (en) * | 1986-05-15 | 1992-10-06 | Emory University | Method for treating vascular obstructions caused by abnormal cells |
US5182106A (en) * | 1986-05-15 | 1993-01-26 | Emory University | Method for treating hypothermia |
US5187191A (en) * | 1990-03-05 | 1993-02-16 | Basf Corp. | Liquid analogs of certain polyoxyalkylene compounds having a plurality of heteric polyoxypropylene/polyoxyethylene chains as dispersants for pesticidal formulations |
US5240701A (en) * | 1986-05-15 | 1993-08-31 | Emory University | Method of performing angioplasty procedures |
US5250294A (en) * | 1986-05-15 | 1993-10-05 | Emory University | Improved perfusion medium for transplantation of organs |
EP0574050A1 (en) | 1992-05-19 | 1993-12-15 | Gist-Brocades N.V. | Large scale separation and purification of fermentation product |
US5286300A (en) * | 1991-02-13 | 1994-02-15 | Man-Gill Chemical Company | Rinse aid and lubricant |
US5298260A (en) * | 1990-05-01 | 1994-03-29 | Mediventures, Inc. | Topical drug delivery with polyoxyalkylene polymer thermoreversible gels adjustable for pH and osmolality |
US5346703A (en) * | 1990-08-07 | 1994-09-13 | Mediventures, Inc. | Body cavity drug delivery with thermo-irreversible polyoxyalkylene and ionic polysaccharide gels |
US5366735A (en) * | 1988-11-16 | 1994-11-22 | Mediventures, Inc. | Method and composition for post-surgical adhesion reduction |
US5470568A (en) * | 1992-02-13 | 1995-11-28 | Arch Development Corporation | Methods and compositions of a polymer (poloxamer) for cell repair |
WO1996003480A1 (en) * | 1994-07-28 | 1996-02-08 | Exxon Research And Engineering Company | Lubricant composition |
US5494660A (en) * | 1985-06-18 | 1996-02-27 | Emory University | Method for inhibiting microbial binding to surfaces |
US5505878A (en) * | 1993-08-16 | 1996-04-09 | Exxon Chemical Patents Inc. | Method of demulsifying water-in-oil emulsions |
EP0707041A1 (en) | 1994-10-11 | 1996-04-17 | Basf Corporation | Improved latex composition employing specifically defined ethylene oxide-propylene oxide block copolymer surfactant and hydrophobic defoaming agent |
US5516452A (en) * | 1994-06-14 | 1996-05-14 | Basf Corporation | Aqueous rinse - aid composition comprising a two - component blend of alkoxylated nonionic surfactants |
US5518648A (en) * | 1994-06-14 | 1996-05-21 | Basf Corporation | Solid dishwashing composition comprising a two-component blend of alkoxylated nonionic surfactants |
US5523492A (en) * | 1991-03-19 | 1996-06-04 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
US5536427A (en) * | 1991-10-23 | 1996-07-16 | Sodick Co., Ltd. | Non-flammable electric discharge machining fluid including a block copolymer |
US5540665A (en) * | 1994-01-31 | 1996-07-30 | Alza Corporation | Gas driven dispensing device and gas generating engine therefor |
US5543068A (en) * | 1988-04-08 | 1996-08-06 | Japan Energy Corporation | Lubricating oils for flon compressors, compositions adapted for flon compressors and composed of mixtures of said lubricating oils and flon, and process for lubricating flon compressor by using said lubricating oils |
US5554372A (en) * | 1986-09-22 | 1996-09-10 | Emory University | Methods and vaccines comprising surface-active copolymers |
US5576470A (en) * | 1994-08-29 | 1996-11-19 | Henkel Corporation | Polyol esters of ether carboxylic acids and fiber finishing methods |
US5605687A (en) * | 1992-05-15 | 1997-02-25 | Arch Development Corporation | Methods and compositions of a polymer (poloxamer) for repair of electrical injury |
WO1997006809A1 (en) * | 1995-08-21 | 1997-02-27 | Cytrx Corporation | Compositions and methods for growth promotion |
US5622649A (en) * | 1991-06-27 | 1997-04-22 | Emory University | Multiple emulsions and methods of preparation |
EP0778339A2 (en) | 1995-12-06 | 1997-06-11 | Basf Corporation | Improved non-phosphate machine dishwashing compositions containing polycarboxylate polymers and nonionic graft copolymers of vinyl acetate and polyalkylene oxide |
EP0778340A2 (en) | 1995-12-06 | 1997-06-11 | Basf Corporation | Improved non-phosphate machine dishwashing compositions containing copolymers of alkylene oxide adducts of allyl alcohol and acrylic acid |
EP0781791A1 (en) | 1995-12-29 | 1997-07-02 | Basf Corporation | Low unsaturation polyoxyalkylene polyether polyols |
US5648071A (en) * | 1986-05-15 | 1997-07-15 | Emory University | Method of treating tumors |
US5674911A (en) * | 1987-02-20 | 1997-10-07 | Cytrx Corporation | Antiinfective polyoxypropylene/polyoxyethylene copolymers and methods of use |
US5696298A (en) * | 1991-03-19 | 1997-12-09 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
US5780417A (en) * | 1997-07-31 | 1998-07-14 | Colgate-Palmolive Company | Light duty liquid cleaning compositions |
US5800711A (en) * | 1996-10-18 | 1998-09-01 | Mdv Technologies, Inc. | Process for the fractionation of polyoxyalkylene block copolymers |
US5811088A (en) * | 1987-02-20 | 1998-09-22 | Emory University | Antiinfective compounds and methods of use |
US5843470A (en) * | 1995-10-06 | 1998-12-01 | Mdv Technologies, Inc. | Method and composition for inhibiting post-surgical adhesions |
US5858529A (en) * | 1995-03-02 | 1999-01-12 | Akzo Nobel Nv | Polyester staple fibers of filaments with high resistance to pilling |
US5858117A (en) * | 1994-08-31 | 1999-01-12 | Ecolab Inc. | Proteolytic enzyme cleaner |
US5861366A (en) * | 1994-08-31 | 1999-01-19 | Ecolab Inc. | Proteolytic enzyme cleaner |
US5867937A (en) * | 1993-03-24 | 1999-02-09 | Smithers-Oasis Company | Method for decreasing hydrophobicity of peat, bark and rockwool in soilless mixes used for plant growth, promoting easier, faster and more even watering of such mixes without plant injury and providing activity for future watering |
US5981624A (en) * | 1996-05-04 | 1999-11-09 | Thetford; Dean | Composition and use |
US6051627A (en) * | 1995-11-30 | 2000-04-18 | Zeneca Limited | Phosphate esters of polyalkylene ether block copolymers and their use as dispersants |
US6086899A (en) * | 1994-08-09 | 2000-07-11 | Cytrx Corporation | Vaccine adjuvant and vaccine |
US6103850A (en) * | 1995-12-29 | 2000-08-15 | Basf Corporation | Sealants made using low unsaturation polyoxyalkylene polyether polyols |
US6280745B1 (en) | 1997-12-23 | 2001-08-28 | Alliance Pharmaceutical Corp. | Methods and compositions for the delivery of pharmaceutical agents and/or the prevention of adhesions |
US6436425B1 (en) | 1988-11-16 | 2002-08-20 | Mdv Technologies, Inc. | Method and non-gelling composition for inhibiting post-surgical adhesions |
US6562770B2 (en) | 2001-03-27 | 2003-05-13 | Colgate-Palmolive Co. | Fragrance-containing gel for delivering fragrance from structured liquid detergent compositions |
US20030153787A1 (en) * | 1997-02-27 | 2003-08-14 | Imperial Chemical Industries Plc | Surfactants |
US20030175322A1 (en) * | 2001-12-21 | 2003-09-18 | Kay John F. | End-capped polymers and compositions containing such compounds |
US20040076677A1 (en) * | 2001-12-21 | 2004-04-22 | Kay John F. | End-capped polymers and compositions containing such compounds |
US20040121932A1 (en) * | 2002-12-19 | 2004-06-24 | Griese Greg G. | Rheology modifier concentrate |
USRE38558E1 (en) | 1991-03-19 | 2004-07-20 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
US20040182425A1 (en) * | 2003-03-21 | 2004-09-23 | Ecolab Inc. | Low temperature cleaning |
US20040248833A1 (en) * | 1991-03-19 | 2004-12-09 | Emanuele R Martin | Therapeutic delivery compositions and methods of use thereof |
US20050062203A1 (en) * | 2003-09-18 | 2005-03-24 | Peter Haas | Release agents, plastics moldings and processes for their production |
US6900167B2 (en) | 2002-10-09 | 2005-05-31 | Ecolab, Inc. | Solid composition with rheology modifier |
US6933286B2 (en) | 1991-03-19 | 2005-08-23 | R. Martin Emanuele | Therapeutic delivery compositions and methods of use thereof |
WO2005095495A1 (en) * | 2004-03-31 | 2005-10-13 | Basf Aktiengesellschaft | Aqueous dispersions with improved ion compatibility and use thereof in paper coating masses |
US20050288380A1 (en) * | 2004-06-29 | 2005-12-29 | Ian Macpherson | Emulsifier/demulsifier system |
US20060257789A1 (en) * | 2005-05-10 | 2006-11-16 | Agfa-Gevaert | Method for processing lithographic printing plates |
US7202225B1 (en) | 1993-10-15 | 2007-04-10 | Emanuele R Martin | Therapeutic delivery compositions and methods of use thereof |
US20070092526A1 (en) * | 2000-06-23 | 2007-04-26 | Evans Robert K | Polynucleotide vaccine adjuvants and formulations containing cationic surfactants, and methods of use |
US20080138310A1 (en) * | 2006-12-11 | 2008-06-12 | Alcon Manufacturing, Ltd. | Use of PEO-PBO block copolymers in ophthalmic compositions |
US20080176083A1 (en) * | 2007-01-18 | 2008-07-24 | Noveon, Inc. | High Moisture Vapor Transmissive Polyurethanes |
US20090007936A1 (en) * | 2005-11-09 | 2009-01-08 | Stephan Uhl | Composition with Surface Modifying Properties |
US20090163616A1 (en) * | 2006-06-12 | 2009-06-25 | Shiseido Company Ltd. | Gel Composition |
US20090202828A1 (en) * | 2004-06-28 | 2009-08-13 | Andrea Pelizzoni | Cable With Environmental Stress Cracking Resistance |
WO2010107635A1 (en) | 2009-03-16 | 2010-09-23 | The Procter & Gamble Company | Method of industrial or institutional laundry for a polyester load |
WO2010107640A1 (en) | 2009-03-16 | 2010-09-23 | The Procter & Gamble Company | Cleaning method |
US20110008276A1 (en) * | 2009-07-07 | 2011-01-13 | Alcon Research, Ltd. | Ethyleneoxide butyleneoxide block copolymer compositions |
US20110039741A1 (en) * | 2008-04-28 | 2011-02-17 | Thoen Johan A | Polyalkylene glycol lubricant composition |
WO2011028993A1 (en) | 2009-09-04 | 2011-03-10 | E. I. Du Pont De Nemours And Company | N-(cyanophenyl)pyrazolecarboxamide aqueous formulation |
WO2011028996A2 (en) | 2009-09-04 | 2011-03-10 | E. I. Du Pont De Nemours And Company | Anthranilic diamide compositions for propagule coating |
US20110079246A1 (en) * | 2009-10-06 | 2011-04-07 | Ecolab Inc. | Daily cleaner with slip-resistant and gloss-enhancing properties |
US20110112004A1 (en) * | 2009-11-12 | 2011-05-12 | Ecolab, Inc. | Composition and methods for removal of polymerized non-trans fats |
WO2011060109A1 (en) | 2009-11-11 | 2011-05-19 | The Procter & Gamble Company | Cleaning method |
WO2011113792A1 (en) | 2010-03-17 | 2011-09-22 | Bayer Materialscience Ag | Process for the production of polyether polyols with a high ethylene oxide content |
WO2011133305A1 (en) | 2010-04-19 | 2011-10-27 | The Procter & Gamble Company | Process for making a liquid detergent composition |
WO2011133378A1 (en) | 2010-04-19 | 2011-10-27 | The Procter & Gamble Company | Process for making a detergent base composition |
US20110306581A1 (en) * | 2008-12-08 | 2011-12-15 | University Of Utah Research Foundation | Stable perfluorocarbon emulsion for use as an artificial oxygen carrier |
WO2012129056A1 (en) | 2011-03-23 | 2012-09-27 | Dow Global Technologies Llc | Polyalkylene glycol based heat transfer fluids and monofluid engine oils |
WO2012160498A2 (en) | 2011-05-20 | 2012-11-29 | Ecolab Usa Inc. | Acid formulations for use in a system for warewashing |
US20130029146A1 (en) * | 2010-04-20 | 2013-01-31 | Nitto Denko Corporation | Water-dispersible acrylic pressure-sensitive adhesive composition and pressure-sensitive adhesive sheet |
WO2013040417A1 (en) | 2011-09-16 | 2013-03-21 | The Charlotte-Mecklenburg Hospital Authority D/B/A Carolinas Medical Center | Amphiphilic cationic polymers for the delivery of therapeutic agents |
WO2013055863A1 (en) | 2011-10-12 | 2013-04-18 | Ecolab Usa Inc. | Moderately alkaline cleaning compositions for proteinaceous and fatty soil removal at low temperatures |
WO2013085914A1 (en) | 2011-12-05 | 2013-06-13 | Ecolab Usa Inc. | Low foaming solid sink detergent |
US8585829B2 (en) | 2010-12-13 | 2013-11-19 | Ecolab Usa Inc. | Soil resistant floor cleaner |
WO2014003839A1 (en) | 2012-06-29 | 2014-01-03 | Ecolab Usa Inc. | Glycerin ether ethoxylate solfactants |
US8637629B2 (en) | 2007-01-18 | 2014-01-28 | Lubrizol Advanced Materials, Inc. | High moisture vapor transmissive polyurethanes |
WO2014084885A1 (en) | 2012-11-28 | 2014-06-05 | Ecolab Usa Inc. | Foam stabilization with polyethyleneimine ethoxylates |
WO2014158761A1 (en) | 2013-03-12 | 2014-10-02 | Ecolab Usa Inc. | Aromatic carboxylic acids in combination with aromatic hydroxyamides for inactivating non-enveloped viruses |
EP2792737A1 (en) | 2011-05-20 | 2014-10-22 | Ecolab USA Inc. | Non-phosphate detergents and non-phosphoric acids in an alternating alkali/acid system for warewashing |
WO2014172280A1 (en) | 2013-04-15 | 2014-10-23 | Ecolab Usa Inc. | Peroxycarboxylic acid based sanitizing rinse additives for use in ware washing |
WO2015030836A1 (en) | 2013-08-27 | 2015-03-05 | Ecolab Usa Inc. | Solid rinse aid composition and method of making same |
US8999312B2 (en) | 2010-06-02 | 2015-04-07 | Alcon Research, Ltd. | Use of PBO-PEO-PBO block copolymers in ophthalmic compositions |
WO2015070117A1 (en) | 2013-11-11 | 2015-05-14 | Ecolab Usa Inc. | High alkaline warewash detergent with enhanced scale control and soil dispersion |
WO2015070119A1 (en) | 2013-11-11 | 2015-05-14 | Ecolab Usa Inc. | Multiuse, enzymatic detergent and methods of stabilizing a use solution |
WO2015073207A1 (en) | 2013-11-14 | 2015-05-21 | Dow Global Technologies Llc | Epoxyamine alkoxylate motor oil dispersants |
WO2015077635A2 (en) | 2013-11-22 | 2015-05-28 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same |
WO2016025206A1 (en) | 2014-08-14 | 2016-02-18 | Ecolab Usa Inc. | Polymers for industrial laundry detergents |
WO2016033563A1 (en) | 2014-08-29 | 2016-03-03 | Ecolab Usa Inc. | Solid rinse aid composition comprising polyacrylic acid |
WO2016187293A1 (en) | 2015-05-19 | 2016-11-24 | Ecolab Usa Inc. | Efficient surfactant system on plastic and all types of ware |
WO2017011158A1 (en) | 2015-07-14 | 2017-01-19 | Ecolab Usa Inc. | Controlled rate of foam breakage in hard surface cleaners |
EP3159394A1 (en) | 2015-10-20 | 2017-04-26 | The Procter and Gamble Company | Method of removing stains by treating fabrics with starch and amylase |
WO2017075384A1 (en) | 2015-10-28 | 2017-05-04 | Ecolab Usa Inc. | Method of using a soil release polymer |
US9670433B1 (en) | 2015-12-28 | 2017-06-06 | Ecolab Usa Inc. | Hard surface cleaning compositions |
WO2017100267A1 (en) | 2015-12-08 | 2017-06-15 | Ecolab Usa Inc. | Pressed manual dish detergent |
WO2017100595A1 (en) | 2015-12-10 | 2017-06-15 | Ecolab Usa Inc. | Abrasion-masking composition for use with reusable containers and the method of using the same |
WO2017201404A1 (en) | 2016-05-19 | 2017-11-23 | Ecolab Usa Inc. | Cleaning compositions for use with calcite-based stone |
WO2018013881A1 (en) | 2016-07-15 | 2018-01-18 | Ecolab Usa Inc. | Aluminum safe degreasing and pre-soak technology for bakery and deli wares and use thereof |
EP3282004A1 (en) | 2011-12-13 | 2018-02-14 | Ecolab USA Inc. | Warewashing method |
WO2018039603A1 (en) | 2016-08-25 | 2018-03-01 | Ecolab Usa Inc. | Cleaning compositions comprising amino acid and methods of use |
WO2018049036A1 (en) | 2016-09-07 | 2018-03-15 | Ecolab Usa Inc. | Detergent compositions containing a stabilized enzyme by phosphonates |
WO2018049029A1 (en) | 2016-09-07 | 2018-03-15 | Ecolab Usa Inc. | Solid detergent compositions and methods of adjusting the dispense rate of solid detergents using solid anionic surfactants |
US9920281B2 (en) | 2009-11-12 | 2018-03-20 | Ecolab Usa Inc. | Soil resistant surface treatment |
WO2018104222A1 (en) | 2016-12-05 | 2018-06-14 | Covestro Deutschland Ag | Use of acrylic acid esters and amides for reducing emissions of a polyurethane foam |
WO2018104221A1 (en) | 2016-12-05 | 2018-06-14 | Covestro Deutschland Ag | Method for producing tdi-based flexible polyurethane foams containing organic acid anhydrides and/or organic acid chlorides |
EP3336115A1 (en) | 2016-12-19 | 2018-06-20 | Covestro Deutschland AG | Process for the reduction of emissions in polyurethane foams |
WO2018160879A2 (en) | 2017-03-01 | 2018-09-07 | Polnox Corporation | Macromolecular corrosion (mcin) inhibitors: structures, methods of making and using the same |
WO2018160818A1 (en) | 2017-03-01 | 2018-09-07 | Ecolab Usa Inc. | Reduced inhalation hazard sanitizers and disinfectants via high molecular weight polymers |
WO2018160809A1 (en) | 2017-03-01 | 2018-09-07 | Ecolab Usa Inc. | Mechanism of urea/solid acid interaction under storage conditions and storage stable solid compositions comprising urea and acid |
WO2018208558A1 (en) | 2017-05-11 | 2018-11-15 | Ecolab Usa Inc. | Compositions and method for floor cleaning or restoration |
EP3456809A1 (en) | 2012-10-04 | 2019-03-20 | Ecolab USA, Inc. | Pre-soak technology for laundry and other hard surface cleaning |
WO2019067608A1 (en) | 2017-09-27 | 2019-04-04 | Ecolab Usa Inc. | Use of eo/po block copolymer surfactant for controlling viscoelasticity in highly concentrated liquid formulations |
WO2019094418A1 (en) | 2017-11-07 | 2019-05-16 | Ecolab Usa Inc. | Alkaline cleaning composition and methods for removing lipstick |
EP3492503A1 (en) | 2017-11-29 | 2019-06-05 | Covestro Deutschland AG | Polyester containing imide |
WO2019108990A1 (en) | 2017-12-01 | 2019-06-06 | Ecolab Usa Inc. | Cleaning compositions and methods for removing baked on grease from fryers and other hot surfaces |
WO2019112744A1 (en) | 2017-12-07 | 2019-06-13 | Ecolab Usa Inc. | Compositions and methods for removing lipstick using branched polyamines |
WO2019148076A1 (en) | 2018-01-26 | 2019-08-01 | Ecolab Usa Inc. | Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a binder and optional carrier |
WO2019148071A1 (en) | 2018-01-26 | 2019-08-01 | Ecolab Usa Inc. | Solidifying liquid anionic surfactants |
WO2019148082A1 (en) | 2018-01-26 | 2019-08-01 | Ecolab Usa Inc | Solid cleaning composition |
WO2019148090A1 (en) | 2018-01-26 | 2019-08-01 | Ecolab Usa Inc. | Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a carrier |
WO2019173688A1 (en) | 2018-03-08 | 2019-09-12 | Ecolab Usa Inc. | Solid enzymatic detergent compositions and methods of use and manufacture |
WO2020006346A1 (en) | 2018-06-29 | 2020-01-02 | Ecolab Usa Inc. | Formula design for a solid laundry fabric softener |
WO2020023693A1 (en) | 2018-07-25 | 2020-01-30 | Ecolab Usa Inc. | Rinse aid formulation for cleaning automotive parts |
WO2020086929A1 (en) | 2018-10-26 | 2020-04-30 | Ecolab Usa Inc. | Synergistic surfactant package for cleaning of food and oily soils |
WO2020113218A2 (en) | 2018-11-30 | 2020-06-04 | Ecolab Usa Inc. | Surfactant compositions and use thereof |
WO2020160429A1 (en) | 2019-01-31 | 2020-08-06 | Ecolab Usa Inc. | Controller for a rinse water reuse system and methods of use |
WO2020159955A1 (en) | 2019-01-29 | 2020-08-06 | Ecolab Usa Inc. | Use of cationic sugar-based compounds as corrosion inhibitors in a water system |
WO2020160425A1 (en) | 2019-01-31 | 2020-08-06 | Ecolab Usa Inc. | Controlling water levels and detergent concentration in a wash cycle |
WO2020160390A1 (en) | 2019-01-31 | 2020-08-06 | Ecolab Usa Inc. | Laundry machine kit to enable control of water levels, recirculation, and spray of chemistry |
WO2020160396A1 (en) | 2019-01-31 | 2020-08-06 | Ecolab Usa Inc. | Rinse water reuse system and methods of use |
WO2020181159A1 (en) | 2019-03-06 | 2020-09-10 | Ecolab Usa Inc. | Concentrated solid hard surface cleaner |
WO2020236873A1 (en) | 2019-05-20 | 2020-11-26 | Ecolab Usa Inc. | Surfactant package for high foaming detergents with low level of medium to long chain linear alcohols |
WO2020257749A1 (en) | 2019-06-21 | 2020-12-24 | Ecolab Usa Inc. | Solid nonionic surfactant compositions |
EP3757200A1 (en) | 2015-08-21 | 2020-12-30 | Ecolab USA Inc. | Pyrithione preservative system in solid rinse aid products |
WO2020264236A1 (en) | 2019-06-28 | 2020-12-30 | Ecolab Usa Inc. | Concentrated solid laundry softener composition |
WO2021022045A1 (en) | 2019-07-31 | 2021-02-04 | Ecolab Usa Inc. | Personal protective equipment free delimer compositions |
WO2021046285A1 (en) | 2019-09-06 | 2021-03-11 | Ecolab Usa Inc. | Concentrated surfactant systems for rinse aid and other applications |
WO2021067407A1 (en) | 2019-09-30 | 2021-04-08 | Ecolab Usa Inc. | Stabilized enzymatic detergent compositions |
WO2021163407A1 (en) | 2020-02-12 | 2021-08-19 | Ecolab Usa Inc. | Use of urea or a urea / chelator combination to chemically stabilize peroxycarboxylic acid and peroxide formulations |
US11103118B2 (en) | 2014-08-01 | 2021-08-31 | Ecolab Usa Inc. | Method of manual surface cleaning using cleaning textiles and of washing said cleaning textiles |
WO2021183990A2 (en) | 2020-03-13 | 2021-09-16 | Harpe Bioherbicide Solutions, Inc. | Herbicidal mentha plant extract compositions and methods of using same |
WO2021195015A1 (en) | 2020-03-23 | 2021-09-30 | Ecolab Usa Inc. | Novel 2-in-1 sanitizing and rinse aid compositions employing amine based surfactants in machine warewashing |
WO2021222675A1 (en) | 2020-04-30 | 2021-11-04 | Ecolab Usa Inc. | Quaternary ammonium sanitizing composition |
WO2021222510A1 (en) | 2020-04-30 | 2021-11-04 | Ecolab Usa Inc. | Low foam cleaning compositions |
WO2021247814A1 (en) | 2020-06-03 | 2021-12-09 | Ecolab Usa Inc. | Non-caustic cleaning methods and uses |
US20220002468A1 (en) * | 2018-11-15 | 2022-01-06 | Ingevity Uk Ltd. | Polyurethane or polyurethane-urea compositions with reduced cold hardening |
WO2022140505A1 (en) | 2020-12-23 | 2022-06-30 | Ecolab Usa Inc. | Soil removal on cotton via treatment in the rinse step for enhanced cleaning in the subsequent wash |
WO2022140522A1 (en) | 2020-12-23 | 2022-06-30 | Ecolab Usa Inc. | Laundry sour softener with extra stability and additional benefits of laundry fire mitigation and sunscreen removal |
WO2022140518A1 (en) | 2020-12-23 | 2022-06-30 | Ecolab Usa Inc. | Non-cationic softeners and methods of use |
EP4047110A1 (en) | 2014-06-20 | 2022-08-24 | Ecolab USA Inc. | Cip method for cleaning using a non-staining high alkaline cleaner |
WO2022221670A2 (en) | 2021-04-15 | 2022-10-20 | Ecolab Usa Inc. | Enzymatic floor cleaning composition |
EP4116397A1 (en) | 2021-07-06 | 2023-01-11 | The Procter & Gamble Company | Whitening additive |
EP4119641A1 (en) | 2015-07-27 | 2023-01-18 | Ecolab USA Inc. | Dry lubricator for plastic and stainless steel surfaces |
WO2023076669A1 (en) | 2021-10-29 | 2023-05-04 | Ecolab Usa Inc. | No rinse quaternary ammonium disinfectant composition for food contact surfaces |
WO2023087195A1 (en) | 2021-11-18 | 2023-05-25 | Ecolab Usa Inc. | Fast drying multi-purpose cleaning and disinfecting compositions and methods of their use |
WO2023087194A1 (en) | 2021-11-18 | 2023-05-25 | Ecolab Usa Inc. | Manual detergent for pot and pan with destaining function |
WO2023122196A1 (en) | 2021-12-22 | 2023-06-29 | Ecolab Usa Inc. | Compositions comprising multiple charged cationic compounds for soil release |
WO2023141490A1 (en) | 2022-01-19 | 2023-07-27 | Ecolab Usa Inc. | Non-fluorocarbon laundry treatment providing enhanced fluid repellency |
EP4230714A1 (en) | 2015-11-12 | 2023-08-23 | Ecolab USA Inc. | Low-foaming warewash detergent containing mixed cationic/nonionic surfactant system for enhanced oily soil removal |
WO2023201319A1 (en) | 2022-04-15 | 2023-10-19 | Ecolab Usa Inc. | Ppe-free tablet degreaser and multipurpose cleaner |
WO2023197233A1 (en) | 2022-04-14 | 2023-10-19 | Ecolab Usa Inc. | Chemo-mechanical solution for cleaning fluidic tanks and piping |
WO2023225624A1 (en) | 2022-05-20 | 2023-11-23 | Ecolab Usa Inc. | Neutral solid and liquid enzymatic rinse aid |
WO2024000340A1 (en) | 2022-06-30 | 2024-01-04 | Ecolab Usa Inc. | Non-silicated metal protectant pressed alkaline detergent and rinse additive |
WO2024031514A1 (en) | 2022-08-11 | 2024-02-15 | Ecolab Usa Inc. | A multipurpose liquid rinse aid |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2549439A (en) * | 1949-09-28 | 1951-04-17 | Petrolite Corp | Processes for breaking petroleum emulsions |
US2552529A (en) * | 1949-07-14 | 1951-05-15 | Petrolite Corp | Process for breaking petroleum emulsions |
-
1953
- 1953-10-19 US US386945A patent/US2674619A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2552529A (en) * | 1949-07-14 | 1951-05-15 | Petrolite Corp | Process for breaking petroleum emulsions |
US2549439A (en) * | 1949-09-28 | 1951-04-17 | Petrolite Corp | Processes for breaking petroleum emulsions |
Cited By (432)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2839477A (en) * | 1958-06-17 | Table ii | ||
US2727867A (en) * | 1951-10-24 | 1955-12-20 | Dearborn Chemicals Co | Method of inhibiting foam formation in steam generating systems |
US2814613A (en) * | 1952-12-31 | 1957-11-26 | British Petroleum Co | Production and/or separation of nonionic surface active agents |
US2876263A (en) * | 1952-12-31 | 1959-03-03 | Universal Oil Prod Co | Polyoxyalkylene cyclic hydrocarbon substituted amines and their ammonium salt derivatives |
US2999045A (en) * | 1953-07-22 | 1961-09-05 | Rayonier Inc | Deresination of wood pulp |
US2979528A (en) * | 1953-10-19 | 1961-04-11 | Wyandotte Chemicals Corp | Nitrogen-containing polyoxyalkylene detergent compositions |
US2786080A (en) * | 1953-11-25 | 1957-03-19 | Wyandotte Chemicals Corp | Stabilized polyoxyalkylene compositions |
US2786796A (en) * | 1953-11-27 | 1957-03-26 | Dow Chemical Co | Method of repelling flies with dibutylphenyl monoether polyglycols |
US2759867A (en) * | 1953-11-27 | 1956-08-21 | Dow Chemical Co | Cyclohexyl-phenol-alkylene-oxide repellent and method |
US2948757A (en) * | 1953-12-07 | 1960-08-09 | Dow Chemical Co | Trihydroxy polyoxyalkylene ethers of glycerol |
US2875128A (en) * | 1953-12-07 | 1959-02-24 | Visco Products Co | Pesticide emulsions containing an oxyethylated oxypropylated glycerine |
US2831034A (en) * | 1953-12-07 | 1958-04-15 | Dow Chemical Co | Polyoxyalkylene glycol ethers of glycerine |
US2802024A (en) * | 1953-12-17 | 1957-08-06 | Exxon Research Engineering Co | Diesters of oxo glycols |
US3121750A (en) * | 1954-06-10 | 1964-02-18 | Petrolite Corp | Oxyalkylated tris(hydroxymethyl)-aminomethanes |
US3121749A (en) * | 1954-06-10 | 1964-02-18 | Petrolite Corp | Oxyalkylated tris(hydroxymethyl)-aminomethanes |
US2870019A (en) * | 1954-09-16 | 1959-01-20 | Upjohn Co | Therapeutic composition |
US2847384A (en) * | 1954-10-19 | 1958-08-12 | Wyandotte Chemicals Corp | Descalant composition and use |
US2805949A (en) * | 1954-10-29 | 1957-09-10 | Dow Chemical Co | Poultry feed |
US2861887A (en) * | 1954-10-29 | 1958-11-25 | Dow Chemical Co | Poultry feed |
US2802736A (en) * | 1954-10-29 | 1957-08-13 | Dow Chemical Co | Poultry feed |
US3232779A (en) * | 1955-01-20 | 1966-02-01 | Mo Och Domsjoe Ab | Methods of producing regenerated cellulose |
US2941892A (en) * | 1955-01-31 | 1960-06-21 | Atlas Powder Co | Spinning of viscose |
US2839476A (en) * | 1955-02-07 | 1958-06-17 | Petrolite Corp | Certain non-ionic surfactants and method of making same |
US3022335A (en) * | 1955-03-30 | 1962-02-20 | Wyandotte Chemicals Corp | Surface active polyoxyalkylene compounds having a plurality of heteric polyoxypropylene-polyoxyethylene chains |
US2771450A (en) * | 1955-04-04 | 1956-11-20 | Petrolite Corp | Process for breaking emulsions |
US2828345A (en) * | 1955-04-27 | 1958-03-25 | Dow Chemical Co | Hydroxypolyoxyethylene diethers of polyoxybutylene glycols |
US2923686A (en) * | 1955-05-23 | 1960-02-02 | Dow Chemical Co | Glycol antifreeze mixtures |
US2805169A (en) * | 1955-07-18 | 1957-09-03 | Rayonier Inc | High-alpha cellulose |
US2898334A (en) * | 1955-07-26 | 1959-08-04 | Rayonier Inc | Cellulose slurry-steeping |
US3077375A (en) * | 1955-08-22 | 1963-02-12 | Atlas Chem Ind | Spinning of viscose |
US3031320A (en) * | 1955-08-22 | 1962-04-24 | Atlas Chem Ind | Spinning of viscose |
US2990396A (en) * | 1955-10-14 | 1961-06-27 | Union Carbide Corp | Production of polymeric materials from polyoxyalkylene polyols and organic polyepoxy compounds |
US2917468A (en) * | 1956-01-18 | 1959-12-15 | Bayer Ag | Surface active polymeric trimethylene oxide derivatives with polyether sidechains, and process for producing same |
US3014073A (en) * | 1956-04-23 | 1961-12-19 | John A Gallaghan | 1, 3-bis(nitroguanidino)-2-nitroxypropane, 1, 3-bis(guanidinium)-2-hydroxy propane and the preparation thereof |
US2977283A (en) * | 1956-04-30 | 1961-03-28 | Upjohn Co | Therapeutic intravenous fat compositions |
US3016305A (en) * | 1956-05-10 | 1962-01-09 | Kunstzijdespinnerij Nyma Nv | Manufacture of thick-skinned or allskin shaped articles from viscose |
US2921920A (en) * | 1956-07-03 | 1960-01-19 | Union Carbide Corp | Polyethylene telomer-polyalkylene oxide block copolymer and method of preparing same |
US2897163A (en) * | 1956-07-09 | 1959-07-28 | Union Carbide Corp | Production of polymeric materials from polyoxyalkylene polyols and butadiene diepoxide |
US2882171A (en) * | 1956-11-14 | 1959-04-14 | Dearborn Chemicals Co | Corrosion inhibiting composition and method |
US2983684A (en) * | 1956-11-28 | 1961-05-09 | Wyandotte Chemicals Corp | Soap composition containing lime soap dispersant |
DE1164670B (en) * | 1957-02-22 | 1964-03-05 | Council Scient Ind Res | Process for the preparation of surface-active compounds from compounds containing active hydrogen atoms and alkylene oxides |
US2950272A (en) * | 1957-03-25 | 1960-08-23 | Visco Products Co | Polyoxyalkylene esters of tall oil rosin acids |
US2923690A (en) * | 1957-03-28 | 1960-02-02 | Jefferson Chem Co Inc | Preparation of high molecular weight polyethylene glycols |
US3036118A (en) * | 1957-09-11 | 1962-05-22 | Wyandotte Chemicals Corp | Mixtures of novel conjugated polyoxyethylene-polyoxypropylene compounds |
US2932670A (en) * | 1957-09-16 | 1960-04-12 | Monsanto Chemicals | Derivatives of glycerol 1, 3-dialkyl ethers and their preparation |
US3112281A (en) * | 1957-09-17 | 1963-11-26 | Wyandotte Chemicals Corp | Polyurethane foams and process for preparing same |
US3031510A (en) * | 1957-10-01 | 1962-04-24 | Economics Lab | Nonionic surface active agent |
US3222300A (en) * | 1957-11-09 | 1965-12-07 | Bayer Ag | Polyurethane plastics from a polyalkylene ether bearing solely terminal hydroxyl groups |
US3020176A (en) * | 1958-03-13 | 1962-02-06 | Mead Corp | Cast coated paper and method of making the same |
US3128314A (en) * | 1958-05-08 | 1964-04-07 | Petrolite Corp | Oxyalkylated condensates |
US3029216A (en) * | 1958-08-11 | 1962-04-10 | Union Carbide Corp | Block copolymer of dissimilar 1, 2-alkylene oxides and process for preparing the same |
DE1161683B (en) * | 1958-08-15 | 1964-01-23 | Ici Ltd | Process for the production of polyurethane foams |
US3101374A (en) * | 1958-08-19 | 1963-08-20 | Wyandotte Chemicals Corp | Polyoxyalkylene surface active agents having heteric polyoxyethylene solubilizing chains |
US3014810A (en) * | 1958-09-08 | 1961-12-26 | Armour & Company Of Delaware | Pigment composition and method of manufacture |
US3110736A (en) * | 1958-09-15 | 1963-11-12 | Petrolite Corp | Certain oxyalkylated polyols |
US3110737A (en) * | 1958-09-15 | 1963-11-12 | Petrolite Corp | Certain oxyalkylated polyols |
DE1149907B (en) * | 1959-02-25 | 1963-06-06 | Basf Ag | Process for the production of higher molecular weight alcohols which contain the grouping -CH-CH-O- |
US3146272A (en) * | 1959-04-02 | 1964-08-25 | Dow Chemical Co | Antioxidants for glycol derivatives |
US3117998A (en) * | 1959-04-14 | 1964-01-14 | Allied Chem | Propylene oxide polyethers |
US3029183A (en) * | 1959-05-18 | 1962-04-10 | West Laboratories Inc | Germicidal iodine compositions |
DE1126140B (en) * | 1959-07-31 | 1962-03-22 | Boehme Fettchemie Gmbh | Process for the production of alkylene oxide addition products with low foaming capacity |
DE1128147B (en) * | 1959-08-01 | 1962-04-19 | Hoechst Ag | Process for the oxaethylation of compounds containing carboxyl groups |
US3117999A (en) * | 1959-08-10 | 1964-01-14 | Rohm & Haas | Tert-carbinamine polyoxyalkylene surface-active agents |
US3118000A (en) * | 1959-08-10 | 1964-01-14 | Rohm & Haas | Polyoxyalkylene surface-active agents |
DE1176358B (en) * | 1959-08-12 | 1964-08-20 | Pittsburgh Plate Glass Co | Process for the production of optionally foamed polyurethanes |
US3156574A (en) * | 1959-09-09 | 1964-11-10 | Ici Ltd | Process of incorporating aqueous pigment composition in viscose |
US3168576A (en) * | 1959-12-10 | 1965-02-02 | Sun Oil Co | Purification of alkyl phenol oxidation inhibitors |
US3231619A (en) * | 1959-12-18 | 1966-01-25 | Jefferson Chem Co Inc | Basic primary amino polyether compositions |
US3161682A (en) * | 1960-04-28 | 1964-12-15 | Jefferson Chem Co Inc | Method for preparing polyoxyalkylene primary amines |
US3133905A (en) * | 1960-05-23 | 1964-05-19 | Goodyear Tire & Rubber | Polyhydroxyl terminated polyethers |
US3167517A (en) * | 1960-08-11 | 1965-01-26 | American Cyanamid Co | Dyeing assistant and leveling compositions |
US3377130A (en) * | 1960-08-11 | 1968-04-09 | American Cyanamid Co | Dyed nitrogenous fibers and anionic dye composition therefor |
US3030197A (en) * | 1960-11-22 | 1962-04-17 | Petrolite Corp | Thermally stable distillate fuels |
US3154498A (en) * | 1960-12-06 | 1964-10-27 | Calgon Corp | Water treating composition |
US3272899A (en) * | 1960-12-06 | 1966-09-13 | Hagan Chemicals & Controls Inc | Process for producing a solid rinse block |
US3162601A (en) * | 1962-01-10 | 1964-12-22 | Pan American Petroleum Corp | Paraffin removal and prevention |
US3380925A (en) * | 1962-05-17 | 1968-04-30 | Henkel & Cie Gmbh | Polyglycol ethers suitable for detergent preparations |
US3406208A (en) * | 1962-05-17 | 1968-10-15 | Henkel & Compagnie G M B H | Polyglycol ethers suitable for detergent preparations, and process for preparing the same |
US3262809A (en) * | 1962-06-29 | 1966-07-26 | Owens Corning Fiberglass Corp | Size composition for glass, and treated glass structures and method for manufacturing same |
US3189653A (en) * | 1962-08-20 | 1965-06-15 | Grace W R & Co | Mono hydrazinium hydroxypolyalkoxy-alkylalkylene-diamines |
US3207791A (en) * | 1962-09-19 | 1965-09-21 | Atlantic Refining Co | Polyalkoxyhydroxyamines |
DE1206877B (en) * | 1963-03-12 | 1965-12-16 | Richard Huttenlocher Dr Ing | Process for the production of surface-active, biodegradable ethers of sugars or polyhydric aliphatic alcohols |
US3256211A (en) * | 1963-06-05 | 1966-06-14 | Union Carbide Corp | Interpolymer of ethylene oxide and at least one different 1, 2-alkylene oxide |
US3250719A (en) * | 1963-09-30 | 1966-05-10 | Wyandotte Chemicals Corp | Foaming detergent compositions |
US3337463A (en) * | 1963-10-18 | 1967-08-22 | Wyandotte Chemicals Corp | Foaming detergent compositions |
US3294540A (en) * | 1963-12-17 | 1966-12-27 | Eastman Kodak Co | Lith-type emulsions with block co-polymers |
US3406236A (en) * | 1964-01-15 | 1968-10-15 | Bayer Ag | Method of molding articles utilizing mold coated with release agent comprising polysiloxane-polyoxyalkylene mixture |
US3383326A (en) * | 1964-03-06 | 1968-05-14 | Nalco Chemical Co | Compositions and processes for breaking petroleum emulsions |
US3314891A (en) * | 1964-05-27 | 1967-04-18 | Wyandotte Chemicals Corp | Low foaming detergent |
US3341456A (en) * | 1964-06-11 | 1967-09-12 | Olin Mathieson | Water-based hydraulic fluid |
US3438907A (en) * | 1965-07-26 | 1969-04-15 | Wyandotte Chemicals Corp | Iodine-containing nonionic surfactant compositions |
US3418218A (en) * | 1966-03-11 | 1968-12-24 | Chrysler Corp | Sealing of aluminum surfaces |
US3925241A (en) * | 1966-09-19 | 1975-12-09 | Basf Wyandotte Corp | Amphoteric surfactant gels |
US3624208A (en) * | 1967-01-20 | 1971-11-30 | Wyandotte Chemicals Corp | Floating bath oil composition |
US3450502A (en) * | 1967-09-25 | 1969-06-17 | Wyandotte Chemicals Corp | Method of operating heart-lung apparatus |
US3900518A (en) * | 1967-10-20 | 1975-08-19 | Gen Tire & Rubber Co | Hydroxyl or thiol terminated telomeric ethers |
US3536497A (en) * | 1967-12-21 | 1970-10-27 | Wyandotte Chemicals Corp | Method for retarding staling of baked goods |
US3867533A (en) * | 1968-12-20 | 1975-02-18 | Basf Wyandotte Corp | Preparation of aqueous gel compositions containing a water-insoluble organic ingredient |
US3866800A (en) * | 1969-02-12 | 1975-02-18 | Alberto Culver Co | Non-pressurized package containing self-heating products |
US3681456A (en) * | 1969-05-26 | 1972-08-01 | Jefferson Chem Co Inc | Thiourea compound |
US3669911A (en) * | 1969-09-26 | 1972-06-13 | Dow Chemical Co | Process and compositions for making porous low density thermoset resins from water-in-resin emulsions |
US3864315A (en) * | 1970-03-23 | 1975-02-04 | Kuraray Co | Fiber-forming polyester composition including a polyalkylene ether |
US4039576A (en) * | 1972-03-28 | 1977-08-02 | Ciba-Geigy Corporation | Process for the manufacture of alkoxylated N-methylol ureas |
US3931336A (en) * | 1972-08-22 | 1976-01-06 | Badische Anilin- & Soda-Fabrik Aktiengesellschaft | Production of oxyalkylated α-hydroxy acetylenic compounds |
US4124527A (en) * | 1973-11-30 | 1978-11-07 | New England Nuclear Corporation | Compositions and process for liquid scintillation counting |
US3939094A (en) * | 1973-11-30 | 1976-02-17 | New England Nuclear Corporation | Compositions and process for liquid scintillation counting |
US3932355A (en) * | 1974-06-19 | 1976-01-13 | E. I. Du Pont De Nemours And Company | Preparation of sol chloroprene polymers |
US4025456A (en) * | 1974-09-20 | 1977-05-24 | Union Carbide Corporation | Polysiloxane-polyoxyalkylene block copolymers |
US4117031A (en) * | 1974-09-26 | 1978-09-26 | Hoechst Aktiengesellschaft | Crude oil demulsifiers |
US4111865A (en) * | 1974-11-13 | 1978-09-05 | Union Carbide Corporation | Polymer/polyols and polyurethane forms and elastomers therefrom |
US4076497A (en) * | 1975-02-01 | 1978-02-28 | Basf Aktiengesellschaft | Continuous dyeing of polyester fibers and cellulose fibers |
US4082703A (en) * | 1975-04-07 | 1978-04-04 | Union Carbide Corporation | Polyurethane prepolymers, rebonded polyurethane foam and methods of forming the same |
US4043752A (en) * | 1975-12-17 | 1977-08-23 | E. I. Du Pont De Nemours And Company | Phenylazoaminophenylpyrazole acid dye solutions containing two nonionic surfactants |
US4102795A (en) * | 1976-04-30 | 1978-07-25 | Kao Soap Co., Ltd. | Softener composition for fabrics or hair |
US4172173A (en) * | 1976-06-30 | 1979-10-23 | Celanese Corporation | Ethylene-vinyl acetate polymer binders for non-woven fabrics |
US4265774A (en) * | 1976-10-29 | 1981-05-05 | Basf Wyandotte Corporation | Oxyalkylated polyglycerols and water-based lubricants prepared therefrom |
US4130477A (en) * | 1976-12-27 | 1978-12-19 | The Dow Chemical Company | Froth flotation process |
US4151269A (en) * | 1977-04-11 | 1979-04-24 | Shiseido Co., Ltd. | Hairdressing preparation |
US4119502A (en) * | 1977-08-17 | 1978-10-10 | M&T Chemicals Inc. | Acid zinc electroplating process and composition |
US4110227A (en) * | 1977-09-19 | 1978-08-29 | Basf Wyandotte Corporation | Oxidation stable polyoxyalkylene fiber lubricants |
US4293428A (en) * | 1978-01-18 | 1981-10-06 | Exxon Production Research Company | Propoxylated ethoxylated surfactants and method of recovering oil therewith |
US4183903A (en) * | 1978-08-02 | 1980-01-15 | Exxon Research & Engineering Co. | Method of removing carbon dioxide from gases utilizing an alkaline absorption solution containing a cyclic urea anti-foaming agent |
US4343716A (en) * | 1978-08-02 | 1982-08-10 | Exxon Research & Engineering Co. | 1-Secondary or 1-tertiary alkyl or cycloalkyl-hexahydro-2-pyrimidinones and 1-secondary or 1-tertiary alkyl or 1-cycloalkyl-2-imidazolidinones and their use as antifoaming agents |
US4208385A (en) * | 1978-08-04 | 1980-06-17 | Exxon Research & Engineering Co. | Process for defoaming acid gas scrubbing solutions and defoaming solutions |
US4312973A (en) * | 1978-08-10 | 1982-01-26 | Union Carbide Corporation | Polyurethane elastomers prepared from polyol or polymer/polyol-chain extender mixtures |
US4358501A (en) * | 1978-08-14 | 1982-11-09 | Ppg Industries, Inc. | Storage stable polyolefin compatible size for fiber glass strands |
US4413085A (en) * | 1978-08-21 | 1983-11-01 | Ppg Industries, Inc. | Storage stable polyolefin compatible non-crosslinking size for fiber glass strands |
US4248935A (en) * | 1978-08-21 | 1981-02-03 | Ppg Industries, Inc. | Storage stable polyolefin compatible non-crosslinking size for fiber glass strands |
US4252540A (en) * | 1978-10-12 | 1981-02-24 | Kao Soap Co., Ltd. | Stabilizer for mixture fuels |
US4332692A (en) * | 1979-02-28 | 1982-06-01 | The Procter & Gamble Company | Laundering with a nonionic detergent system at a temperature between the cloud point and the phase coalescence temperatures |
US4252969A (en) * | 1979-09-27 | 1981-02-24 | National Distillers And Chemical Corp. | Process for regulating particle size of finely divided thermoplastic resins |
US4288639A (en) * | 1979-10-22 | 1981-09-08 | Basf Wyandotte Corporation | Alpha-olefin oxide-modified liquid polyether thickeners |
US4395351A (en) * | 1979-10-22 | 1983-07-26 | Camp Ronald L | Polyether-based thickeners with additives for increased efficiency in aqueous systems |
US4428860A (en) | 1979-10-22 | 1984-01-31 | Basf Wyandotte Corporation | Polyether thickeners for aqueous systems containing additives for increased thickening efficiency |
US4665239A (en) * | 1979-10-22 | 1987-05-12 | Basf Corporation | Polyethers modified with alpha olefin oxides |
US4312775A (en) * | 1979-10-22 | 1982-01-26 | Basf Wyandotte Corporation | Polyether thickeners for aqueous systems containing additives for increased thickening efficiency |
US4310436A (en) * | 1979-10-22 | 1982-01-12 | Basf Wyandotte | Polyether-based thickeners with additives for increased efficiency in aqueous systems |
US4288232A (en) * | 1979-12-19 | 1981-09-08 | Basf Wyandotte Corporation | Ester containing fuel composition |
US4276054A (en) * | 1979-12-19 | 1981-06-30 | Basf Wyandotte Corporation | Coal-oil slurries containing a surfactant |
US4340766A (en) * | 1980-02-14 | 1982-07-20 | Basf Aktiengesellschaft | Dishwashing agents and cleaning agents containing oxybutylated higher alcohol/ethylene oxide adducts as low-foaming surfactants |
US4464193A (en) * | 1980-02-19 | 1984-08-07 | Basf Wyandotte Corporation | Anionic biocide emulsions in aqueous solutions of strongly ionizable salts |
US4333488A (en) * | 1980-09-08 | 1982-06-08 | Conoco Inc. | Method of transporting viscous hydrocarbons |
US4351753A (en) * | 1980-10-24 | 1982-09-28 | Basf Wyandotte Corporation | Liquified normally solid polyoxyalkylene block copolymers |
US4434078A (en) | 1980-10-24 | 1984-02-28 | Basf Wyandotte Corporation | Liquefied normally solid polyoxyalkylene copolymers |
US4434077A (en) | 1980-10-24 | 1984-02-28 | Basf Wyandotte Corporation | Liquefied normally solid polyoxyalkylene copolymers |
EP0051878A1 (en) * | 1980-11-12 | 1982-05-19 | Union Carbide Corporation | Low-foaming nonionic surfactants |
DE3144371A1 (en) * | 1980-11-13 | 1982-06-09 | Basf Ag, 6700 Ludwigshafen | Low-foam and biodegradable alkoxylation products whose end groups are blocked by glycerol ether radicals, a process for their preparation and their use as surfactants in detergents and cleaning agents |
US4323467A (en) * | 1980-11-24 | 1982-04-06 | Syntex (U.S.A.) Inc. | Contact lens cleaning, storing and wetting solutions |
US4340382A (en) * | 1980-12-16 | 1982-07-20 | Union Carbide Corporation | Method for treating and processing textile materials |
US4317940A (en) * | 1980-12-23 | 1982-03-02 | Olin Corporation | Biodegradable surfactants |
US4358293A (en) * | 1981-01-29 | 1982-11-09 | Gulf & Western Manufacturing Co. | Coal-aqueous mixtures |
US4406798A (en) * | 1981-08-24 | 1983-09-27 | Pfizer Inc. | Surfactant enhanced injectivity of xanthan mobility control solutions for tertiary oil recovery |
US4601836A (en) * | 1981-10-13 | 1986-07-22 | Jones L W | Phosphate ester/alcohol micellar solutions in well acidizing |
US4411810A (en) * | 1981-11-06 | 1983-10-25 | Basf Wyandotte Corporation | Low-foaming nonionic surfactant for machine dishwashing detergent |
US4469606A (en) * | 1982-07-26 | 1984-09-04 | Ciba-Geigy Corporation | Stabilization systems for fiber finishes |
US4483741A (en) * | 1982-08-10 | 1984-11-20 | Economics Laboratory, Inc. | Low-foaming, pH sensitive, alkylamine polyether surface active agents and methods for using |
US4605773A (en) * | 1982-08-10 | 1986-08-12 | Diamond Shamrock Chemicals Company | Low-foaming, pH sensitive, alkylamine polyether surface active agents and methods for using |
US4506018A (en) * | 1982-12-30 | 1985-03-19 | Becton, Dickinson And Company | Blood diluent |
JPS6319558B2 (en) * | 1983-04-13 | 1988-04-22 | Kao Corp | |
JPS58223430A (en) * | 1983-04-13 | 1983-12-26 | Kao Corp | Aqueous dispersion stabilizer of fine coal powder |
US4594366A (en) * | 1983-06-29 | 1986-06-10 | Union Carbide Corporation | Connected branched polyols and polyurethanes based thereon |
US4534958A (en) * | 1983-07-13 | 1985-08-13 | Basf Wyandotte Corporation | Aerosol gel |
US4606918A (en) * | 1983-08-22 | 1986-08-19 | Syntex (U.S.A.) Inc. | Polyoxypropylene-polyoxyethylene block polymer based adjuvants |
US4933179A (en) * | 1983-08-22 | 1990-06-12 | Syntex (U.S.A.) Inc. | Feline leukemia virus antigen vaccines |
US4534959A (en) * | 1983-08-22 | 1985-08-13 | Basf Wyandotte Corporation | Aerosol gel |
US5494660A (en) * | 1985-06-18 | 1996-02-27 | Emory University | Method for inhibiting microbial binding to surfaces |
US4661275A (en) * | 1985-07-29 | 1987-04-28 | The Lubrizol Corporation | Water-based functional fluid thickening combinations of surfactants and hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products |
US4664834A (en) * | 1985-07-29 | 1987-05-12 | The Lubrizol Corporation | Hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products, and aqueous systems containing same |
US4618442A (en) * | 1985-10-07 | 1986-10-21 | Geary Robert J | Plant cryoprotection |
US4676916A (en) * | 1985-12-02 | 1987-06-30 | Basf Corporation | Acidizing concentrates for oil well acidizing systems |
US4726909A (en) * | 1985-12-23 | 1988-02-23 | Basf Corporation | Low odor surfactant |
US4836951A (en) * | 1986-02-19 | 1989-06-06 | Union Carbide Corporation | Random polyether foam control agents |
US5124389A (en) * | 1986-03-17 | 1992-06-23 | Mente Donald C | Thickening aqueous systems |
US4937070A (en) * | 1986-05-15 | 1990-06-26 | Emory University | Methods and compositions for treatment of pathological hydrophobic interactions in biological fluids |
US5250294A (en) * | 1986-05-15 | 1993-10-05 | Emory University | Improved perfusion medium for transplantation of organs |
US5648071A (en) * | 1986-05-15 | 1997-07-15 | Emory University | Method of treating tumors |
US5240701A (en) * | 1986-05-15 | 1993-08-31 | Emory University | Method of performing angioplasty procedures |
US5182106A (en) * | 1986-05-15 | 1993-01-26 | Emory University | Method for treating hypothermia |
US5152979A (en) * | 1986-05-15 | 1992-10-06 | Emory University | Method for treating vascular obstructions caused by abnormal cells |
US5089260A (en) * | 1986-05-15 | 1992-02-18 | Emory University | Method of treating ischemic tissue |
US5080894A (en) * | 1986-05-15 | 1992-01-14 | Emory University | Method and composition for reducing tissue damage |
US4997644A (en) * | 1986-05-15 | 1991-03-05 | Emory University | Method of treating adult respiratory distress syndrome |
US5017370A (en) * | 1986-05-15 | 1991-05-21 | Emory University | Improved method of performing angioplasty procedures |
US5078995A (en) * | 1986-05-15 | 1992-01-07 | Emory University | Fibrionolytic composition |
US5028599A (en) * | 1986-05-15 | 1991-07-02 | Emory University | Method of treating mycardial damage |
US5071649A (en) * | 1986-05-15 | 1991-12-10 | Emory University | Method of preventing blockage in catheters |
US5030448A (en) * | 1986-05-15 | 1991-07-09 | Emory University | Method of delivering drugs to damaged or diseased tissue |
US5032394A (en) * | 1986-05-15 | 1991-07-16 | Emory University | Method of treating burns |
US5047236A (en) * | 1986-05-15 | 1991-09-10 | Emory University | Method of treating stroke |
US5039520A (en) * | 1986-05-15 | 1991-08-13 | Emory University | Plasma extender |
US5041288A (en) * | 1986-05-15 | 1991-08-20 | Emory University | Method of treating tissue damaged by reperfusion injury |
WO1988001272A2 (en) | 1986-08-14 | 1988-02-25 | The Lubrizol Corporation | Borated amine salts of monothiophosphoric acids |
WO1988001873A1 (en) * | 1986-09-22 | 1988-03-24 | Emory University | Vaccine and method of preparation |
US5554372A (en) * | 1986-09-22 | 1996-09-10 | Emory University | Methods and vaccines comprising surface-active copolymers |
EP0268920A1 (en) * | 1986-11-21 | 1988-06-01 | BASF Corporation | Process for preparing capped polyoxyalkylene block polyethers |
US4902834A (en) * | 1986-11-21 | 1990-02-20 | Basf Corporation | Process for preparing capped polyoxyalkylene block polyethers |
US5811088A (en) * | 1987-02-20 | 1998-09-22 | Emory University | Antiinfective compounds and methods of use |
US5674911A (en) * | 1987-02-20 | 1997-10-07 | Cytrx Corporation | Antiinfective polyoxypropylene/polyoxyethylene copolymers and methods of use |
JPH01503458A (en) * | 1987-02-20 | 1989-11-22 | エモリ ユニバーシティ | anti-infective compounds |
US5103062A (en) * | 1987-04-10 | 1992-04-07 | Texaco Inc. | Modified normally liquid, water-soluble polyoxyalkylene polyamines |
US4886609A (en) * | 1987-10-09 | 1989-12-12 | Gaf Corporation | Method for stimulation of oil and gas wells |
US4965019A (en) * | 1988-01-11 | 1990-10-23 | Henkel Kommanditgesellschaft Auf Aktien | Use of selected end-group closed fatty alcohol ethoxylates for low-foam, cold-sprayable cleaning agents |
US5543068A (en) * | 1988-04-08 | 1996-08-06 | Japan Energy Corporation | Lubricating oils for flon compressors, compositions adapted for flon compressors and composed of mixtures of said lubricating oils and flon, and process for lubricating flon compressor by using said lubricating oils |
US4859358A (en) * | 1988-06-09 | 1989-08-22 | The Procter & Gamble Company | Liquid automatic dishwashing compositions containing metal salts of hydroxy fatty acids providing silver protection |
US5130043A (en) * | 1988-06-09 | 1992-07-14 | The Procter & Gamble Company | Liquid automatic dishwashing compositions having enhanced stability |
US4988452A (en) * | 1988-06-09 | 1991-01-29 | The Procter & Gamble Company | Liquid automatic dishwashing detergent compositions containing bleach-stable nonionic surfactant |
US5028353A (en) * | 1988-10-07 | 1991-07-02 | Colgate-Palmolive Company | Process of preparing a combination detergent and soap bar with enhanced mildness |
US5135751A (en) * | 1988-11-16 | 1992-08-04 | Mediventures Incorporated | Composition for reducing postsurgical adhesions |
US6436425B1 (en) | 1988-11-16 | 2002-08-20 | Mdv Technologies, Inc. | Method and non-gelling composition for inhibiting post-surgical adhesions |
US5366735A (en) * | 1988-11-16 | 1994-11-22 | Mediventures, Inc. | Method and composition for post-surgical adhesion reduction |
US5026734A (en) * | 1989-01-12 | 1991-06-25 | Browning Henry A | Method of controlling fungus, mites, worms, termites, nematodes and other insects |
US5126068A (en) * | 1989-05-05 | 1992-06-30 | Burke John J | Hard surface cleaning composition containing polyacrylate copolymers as performance boosters |
US5064583A (en) * | 1989-08-01 | 1991-11-12 | Zycon Corporation | Method for applying mold release coating to separator plates for molding printed circuit boards |
EP0439755A2 (en) | 1990-01-29 | 1991-08-07 | BASF Corporation | Process for preparing graft polyols and the polyols prepared thereby |
US5187191A (en) * | 1990-03-05 | 1993-02-16 | Basf Corp. | Liquid analogs of certain polyoxyalkylene compounds having a plurality of heteric polyoxypropylene/polyoxyethylene chains as dispersants for pesticidal formulations |
US5298260A (en) * | 1990-05-01 | 1994-03-29 | Mediventures, Inc. | Topical drug delivery with polyoxyalkylene polymer thermoreversible gels adjustable for pH and osmolality |
US5346703A (en) * | 1990-08-07 | 1994-09-13 | Mediventures, Inc. | Body cavity drug delivery with thermo-irreversible polyoxyalkylene and ionic polysaccharide gels |
US6346272B1 (en) | 1990-08-07 | 2002-02-12 | Mdv Technologies, Inc. | Body cavity drug delivery with thermo-irreversible polyoxyalkylene and ionic polysaccharide gels |
US5312389A (en) * | 1990-10-29 | 1994-05-17 | Felix Theeuwes | Osmotically driven syringe with programmable agent delivery |
US5151093A (en) * | 1990-10-29 | 1992-09-29 | Alza Corporation | Osmotically driven syringe with programmable agent delivery |
US5286300A (en) * | 1991-02-13 | 1994-02-15 | Man-Gill Chemical Company | Rinse aid and lubricant |
US6933286B2 (en) | 1991-03-19 | 2005-08-23 | R. Martin Emanuele | Therapeutic delivery compositions and methods of use thereof |
USRE37285E1 (en) | 1991-03-19 | 2001-07-17 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolmers with improved biological activity |
US5523492A (en) * | 1991-03-19 | 1996-06-04 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
US6747064B2 (en) | 1991-03-19 | 2004-06-08 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
USRE38558E1 (en) | 1991-03-19 | 2004-07-20 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
US6359014B1 (en) | 1991-03-19 | 2002-03-19 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
US5990241A (en) * | 1991-03-19 | 1999-11-23 | Cytrx, Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
US20040248833A1 (en) * | 1991-03-19 | 2004-12-09 | Emanuele R Martin | Therapeutic delivery compositions and methods of use thereof |
US5696298A (en) * | 1991-03-19 | 1997-12-09 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
US5691387A (en) * | 1991-03-19 | 1997-11-25 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolmers with improved biological activity |
USRE36665E (en) * | 1991-03-19 | 2000-04-18 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
US5622649A (en) * | 1991-06-27 | 1997-04-22 | Emory University | Multiple emulsions and methods of preparation |
US5536427A (en) * | 1991-10-23 | 1996-07-16 | Sodick Co., Ltd. | Non-flammable electric discharge machining fluid including a block copolymer |
US5470568A (en) * | 1992-02-13 | 1995-11-28 | Arch Development Corporation | Methods and compositions of a polymer (poloxamer) for cell repair |
US5605687A (en) * | 1992-05-15 | 1997-02-25 | Arch Development Corporation | Methods and compositions of a polymer (poloxamer) for repair of electrical injury |
EP0574050A1 (en) | 1992-05-19 | 1993-12-15 | Gist-Brocades N.V. | Large scale separation and purification of fermentation product |
US6079153A (en) * | 1993-03-24 | 2000-06-27 | Smithers-Oasis Company | Method for decreasing hydrophobicity of peat, bark and rock-wool, soilless mixes used for plant growth, promoting easier, faster and more even watering of such mixes without plant injury and providing residual activity for future watering |
US5867937A (en) * | 1993-03-24 | 1999-02-09 | Smithers-Oasis Company | Method for decreasing hydrophobicity of peat, bark and rockwool in soilless mixes used for plant growth, promoting easier, faster and more even watering of such mixes without plant injury and providing activity for future watering |
US5505878A (en) * | 1993-08-16 | 1996-04-09 | Exxon Chemical Patents Inc. | Method of demulsifying water-in-oil emulsions |
US7202225B1 (en) | 1993-10-15 | 2007-04-10 | Emanuele R Martin | Therapeutic delivery compositions and methods of use thereof |
US5540665A (en) * | 1994-01-31 | 1996-07-30 | Alza Corporation | Gas driven dispensing device and gas generating engine therefor |
US5516452A (en) * | 1994-06-14 | 1996-05-14 | Basf Corporation | Aqueous rinse - aid composition comprising a two - component blend of alkoxylated nonionic surfactants |
US5518648A (en) * | 1994-06-14 | 1996-05-21 | Basf Corporation | Solid dishwashing composition comprising a two-component blend of alkoxylated nonionic surfactants |
WO1996003480A1 (en) * | 1994-07-28 | 1996-02-08 | Exxon Research And Engineering Company | Lubricant composition |
US20050070670A1 (en) * | 1994-08-09 | 2005-03-31 | Mannarsamy Balasubramanian | Novel adjuvants and copolymer compositions |
US6086899A (en) * | 1994-08-09 | 2000-07-11 | Cytrx Corporation | Vaccine adjuvant and vaccine |
US6844001B2 (en) | 1994-08-09 | 2005-01-18 | Cyt Rx Corporation | Adjuvants and copolymer compositions |
US6416947B1 (en) | 1994-08-09 | 2002-07-09 | Cytrx Corporation | Vaccine adjuvant and vaccine method |
US6149922A (en) * | 1994-08-09 | 2000-11-21 | Cytrx Corporation | Vaccine adjuvant and vaccine |
US7045576B2 (en) | 1994-08-09 | 2006-05-16 | Cytrx Corporation | Adjuvants and copolymer compositions |
US5576470A (en) * | 1994-08-29 | 1996-11-19 | Henkel Corporation | Polyol esters of ether carboxylic acids and fiber finishing methods |
US5861366A (en) * | 1994-08-31 | 1999-01-19 | Ecolab Inc. | Proteolytic enzyme cleaner |
US6197739B1 (en) | 1994-08-31 | 2001-03-06 | Ecolab Inc. | Proteolytic enzyme cleaner |
US5858117A (en) * | 1994-08-31 | 1999-01-12 | Ecolab Inc. | Proteolytic enzyme cleaner |
EP0707041A1 (en) | 1994-10-11 | 1996-04-17 | Basf Corporation | Improved latex composition employing specifically defined ethylene oxide-propylene oxide block copolymer surfactant and hydrophobic defoaming agent |
US5858529A (en) * | 1995-03-02 | 1999-01-12 | Akzo Nobel Nv | Polyester staple fibers of filaments with high resistance to pilling |
WO1997006809A1 (en) * | 1995-08-21 | 1997-02-27 | Cytrx Corporation | Compositions and methods for growth promotion |
US5824322A (en) * | 1995-08-21 | 1998-10-20 | Cytrx Corporation | Compositions and methods for growth promotion |
US6034088A (en) * | 1995-10-06 | 2000-03-07 | Mdv Technologies, Inc. | Method and composition for inhibiting post-surgical adhesions |
US5843470A (en) * | 1995-10-06 | 1998-12-01 | Mdv Technologies, Inc. | Method and composition for inhibiting post-surgical adhesions |
US6051627A (en) * | 1995-11-30 | 2000-04-18 | Zeneca Limited | Phosphate esters of polyalkylene ether block copolymers and their use as dispersants |
EP0778339A2 (en) | 1995-12-06 | 1997-06-11 | Basf Corporation | Improved non-phosphate machine dishwashing compositions containing polycarboxylate polymers and nonionic graft copolymers of vinyl acetate and polyalkylene oxide |
EP0778340A2 (en) | 1995-12-06 | 1997-06-11 | Basf Corporation | Improved non-phosphate machine dishwashing compositions containing copolymers of alkylene oxide adducts of allyl alcohol and acrylic acid |
EP0781791A1 (en) | 1995-12-29 | 1997-07-02 | Basf Corporation | Low unsaturation polyoxyalkylene polyether polyols |
US6103850A (en) * | 1995-12-29 | 2000-08-15 | Basf Corporation | Sealants made using low unsaturation polyoxyalkylene polyether polyols |
US20030108610A1 (en) * | 1996-02-09 | 2003-06-12 | Flore Stephen G. | Methods and compositions for the delivery of pharmaceutical agents and/or the prevention of adhesions |
US5981624A (en) * | 1996-05-04 | 1999-11-09 | Thetford; Dean | Composition and use |
US6069210A (en) * | 1996-05-04 | 2000-05-30 | Zeneca Limited | Phosphate esters of polyoxyalkylene ether block copolymers and their dispersants |
US5800711A (en) * | 1996-10-18 | 1998-09-01 | Mdv Technologies, Inc. | Process for the fractionation of polyoxyalkylene block copolymers |
US20030153787A1 (en) * | 1997-02-27 | 2003-08-14 | Imperial Chemical Industries Plc | Surfactants |
US5780417A (en) * | 1997-07-31 | 1998-07-14 | Colgate-Palmolive Company | Light duty liquid cleaning compositions |
US6280745B1 (en) | 1997-12-23 | 2001-08-28 | Alliance Pharmaceutical Corp. | Methods and compositions for the delivery of pharmaceutical agents and/or the prevention of adhesions |
US20070092526A1 (en) * | 2000-06-23 | 2007-04-26 | Evans Robert K | Polynucleotide vaccine adjuvants and formulations containing cationic surfactants, and methods of use |
US6562770B2 (en) | 2001-03-27 | 2003-05-13 | Colgate-Palmolive Co. | Fragrance-containing gel for delivering fragrance from structured liquid detergent compositions |
US7205337B2 (en) | 2001-12-21 | 2007-04-17 | Isotis Orthobiologics, Inc. | End-capped polymers and compositions containing such compounds |
US20040076677A1 (en) * | 2001-12-21 | 2004-04-22 | Kay John F. | End-capped polymers and compositions containing such compounds |
US7241813B2 (en) | 2001-12-21 | 2007-07-10 | Isotis Orthobiologics, Inc. | End-capped polymers and compositions containing such compounds |
US20030175322A1 (en) * | 2001-12-21 | 2003-09-18 | Kay John F. | End-capped polymers and compositions containing such compounds |
US6900167B2 (en) | 2002-10-09 | 2005-05-31 | Ecolab, Inc. | Solid composition with rheology modifier |
US6903062B2 (en) | 2002-12-19 | 2005-06-07 | Ecolab, Inc. | Rheology modifier concentrate |
US20040121932A1 (en) * | 2002-12-19 | 2004-06-24 | Griese Greg G. | Rheology modifier concentrate |
US6953507B2 (en) | 2003-03-21 | 2005-10-11 | Ecolab Inc. | Low temperature cleaning |
US20040182425A1 (en) * | 2003-03-21 | 2004-09-23 | Ecolab Inc. | Low temperature cleaning |
US20050062203A1 (en) * | 2003-09-18 | 2005-03-24 | Peter Haas | Release agents, plastics moldings and processes for their production |
WO2005095495A1 (en) * | 2004-03-31 | 2005-10-13 | Basf Aktiengesellschaft | Aqueous dispersions with improved ion compatibility and use thereof in paper coating masses |
US8475920B2 (en) | 2004-06-28 | 2013-07-02 | Prysmian Cavi E Sistemi Energia Srl | Cable with environmental stress cracking resistance |
US20090202828A1 (en) * | 2004-06-28 | 2009-08-13 | Andrea Pelizzoni | Cable With Environmental Stress Cracking Resistance |
US20050288380A1 (en) * | 2004-06-29 | 2005-12-29 | Ian Macpherson | Emulsifier/demulsifier system |
US20060257789A1 (en) * | 2005-05-10 | 2006-11-16 | Agfa-Gevaert | Method for processing lithographic printing plates |
US20090007936A1 (en) * | 2005-11-09 | 2009-01-08 | Stephan Uhl | Composition with Surface Modifying Properties |
US8969278B2 (en) | 2005-11-09 | 2015-03-03 | Ecolab Usa Inc. | Composition with surface modifying properties |
US8093195B2 (en) | 2005-11-09 | 2012-01-10 | Ecolab Usa Inc. | Composition with surface modifying properties |
US20090163616A1 (en) * | 2006-06-12 | 2009-06-25 | Shiseido Company Ltd. | Gel Composition |
US7973085B2 (en) * | 2006-06-12 | 2011-07-05 | Shiseido Company Ltd. | Gel composition |
US9574160B2 (en) | 2006-12-11 | 2017-02-21 | Alcon Research, Ltd. | Use of PEO-PBO block copolymers in ophthalmic compositions |
US20110059039A1 (en) * | 2006-12-11 | 2011-03-10 | Alcon Research, Ltd. | Use of peo-pbo block copolymers in ophthalmic compositions |
US8318144B2 (en) | 2006-12-11 | 2012-11-27 | Alcon Research, Ltd. | Use of PEO-PBO block copolymers in ophthalmic compositions |
US20080138310A1 (en) * | 2006-12-11 | 2008-06-12 | Alcon Manufacturing, Ltd. | Use of PEO-PBO block copolymers in ophthalmic compositions |
US20080176083A1 (en) * | 2007-01-18 | 2008-07-24 | Noveon, Inc. | High Moisture Vapor Transmissive Polyurethanes |
US8637629B2 (en) | 2007-01-18 | 2014-01-28 | Lubrizol Advanced Materials, Inc. | High moisture vapor transmissive polyurethanes |
US20110039741A1 (en) * | 2008-04-28 | 2011-02-17 | Thoen Johan A | Polyalkylene glycol lubricant composition |
US8592357B2 (en) | 2008-04-28 | 2013-11-26 | Dow Global Technologies Llc | Polyalkylene glycol lubricant composition |
US8357644B2 (en) | 2008-04-28 | 2013-01-22 | Dow Global Technologies Llc | Polyalkylene glycol lubricant composition |
US20110306581A1 (en) * | 2008-12-08 | 2011-12-15 | University Of Utah Research Foundation | Stable perfluorocarbon emulsion for use as an artificial oxygen carrier |
US8673984B2 (en) * | 2008-12-08 | 2014-03-18 | University Of Utah Research Foundation | Stable perfluorocarbon emulsion for use as an artificial oxygen carrier |
WO2010107640A1 (en) | 2009-03-16 | 2010-09-23 | The Procter & Gamble Company | Cleaning method |
WO2010107635A1 (en) | 2009-03-16 | 2010-09-23 | The Procter & Gamble Company | Method of industrial or institutional laundry for a polyester load |
US20110008276A1 (en) * | 2009-07-07 | 2011-01-13 | Alcon Research, Ltd. | Ethyleneoxide butyleneoxide block copolymer compositions |
US9175249B2 (en) | 2009-07-07 | 2015-11-03 | Alcon Research, Ltd. | Ethyleneoxide butyleneoxide block copolymer compositions |
WO2011028996A2 (en) | 2009-09-04 | 2011-03-10 | E. I. Du Pont De Nemours And Company | Anthranilic diamide compositions for propagule coating |
WO2011028993A1 (en) | 2009-09-04 | 2011-03-10 | E. I. Du Pont De Nemours And Company | N-(cyanophenyl)pyrazolecarboxamide aqueous formulation |
US8206511B2 (en) | 2009-10-06 | 2012-06-26 | Ecolab Usa Inc. | Daily cleaner with slip-resistant and gloss-enhancing properties |
US20110079246A1 (en) * | 2009-10-06 | 2011-04-07 | Ecolab Inc. | Daily cleaner with slip-resistant and gloss-enhancing properties |
WO2011060109A1 (en) | 2009-11-11 | 2011-05-19 | The Procter & Gamble Company | Cleaning method |
US9920281B2 (en) | 2009-11-12 | 2018-03-20 | Ecolab Usa Inc. | Soil resistant surface treatment |
US20110112004A1 (en) * | 2009-11-12 | 2011-05-12 | Ecolab, Inc. | Composition and methods for removal of polymerized non-trans fats |
US8222196B2 (en) | 2009-11-12 | 2012-07-17 | Ecolab Usa Inc. | Composition and methods for removal of polymerized non-trans fats |
US9376651B2 (en) | 2009-11-12 | 2016-06-28 | Ecolab Usa Inc. | Soil resistant floor treatment |
WO2011113792A1 (en) | 2010-03-17 | 2011-09-22 | Bayer Materialscience Ag | Process for the production of polyether polyols with a high ethylene oxide content |
WO2011133305A1 (en) | 2010-04-19 | 2011-10-27 | The Procter & Gamble Company | Process for making a liquid detergent composition |
WO2011133378A1 (en) | 2010-04-19 | 2011-10-27 | The Procter & Gamble Company | Process for making a detergent base composition |
US20130029146A1 (en) * | 2010-04-20 | 2013-01-31 | Nitto Denko Corporation | Water-dispersible acrylic pressure-sensitive adhesive composition and pressure-sensitive adhesive sheet |
US9521842B2 (en) | 2010-06-02 | 2016-12-20 | Alcon Research, Ltd. | Use of PBO-PEO-PBO block copolymers in ophthalmic compositions |
US8999312B2 (en) | 2010-06-02 | 2015-04-07 | Alcon Research, Ltd. | Use of PBO-PEO-PBO block copolymers in ophthalmic compositions |
US8585829B2 (en) | 2010-12-13 | 2013-11-19 | Ecolab Usa Inc. | Soil resistant floor cleaner |
WO2012129056A1 (en) | 2011-03-23 | 2012-09-27 | Dow Global Technologies Llc | Polyalkylene glycol based heat transfer fluids and monofluid engine oils |
EP2902471A1 (en) | 2011-05-20 | 2015-08-05 | Ecolab USA Inc. | Non-phosphate detergents and non-phosphoric acids in an alternating alkali/acid system for warewashing |
WO2012160498A2 (en) | 2011-05-20 | 2012-11-29 | Ecolab Usa Inc. | Acid formulations for use in a system for warewashing |
EP2792737A1 (en) | 2011-05-20 | 2014-10-22 | Ecolab USA Inc. | Non-phosphate detergents and non-phosphoric acids in an alternating alkali/acid system for warewashing |
WO2013040417A1 (en) | 2011-09-16 | 2013-03-21 | The Charlotte-Mecklenburg Hospital Authority D/B/A Carolinas Medical Center | Amphiphilic cationic polymers for the delivery of therapeutic agents |
WO2013055863A1 (en) | 2011-10-12 | 2013-04-18 | Ecolab Usa Inc. | Moderately alkaline cleaning compositions for proteinaceous and fatty soil removal at low temperatures |
WO2013085914A1 (en) | 2011-12-05 | 2013-06-13 | Ecolab Usa Inc. | Low foaming solid sink detergent |
EP3282004A1 (en) | 2011-12-13 | 2018-02-14 | Ecolab USA Inc. | Warewashing method |
WO2014003839A1 (en) | 2012-06-29 | 2014-01-03 | Ecolab Usa Inc. | Glycerin ether ethoxylate solfactants |
EP3456809A1 (en) | 2012-10-04 | 2019-03-20 | Ecolab USA, Inc. | Pre-soak technology for laundry and other hard surface cleaning |
WO2014084885A1 (en) | 2012-11-28 | 2014-06-05 | Ecolab Usa Inc. | Foam stabilization with polyethyleneimine ethoxylates |
WO2014158761A1 (en) | 2013-03-12 | 2014-10-02 | Ecolab Usa Inc. | Aromatic carboxylic acids in combination with aromatic hydroxyamides for inactivating non-enveloped viruses |
WO2014172280A1 (en) | 2013-04-15 | 2014-10-23 | Ecolab Usa Inc. | Peroxycarboxylic acid based sanitizing rinse additives for use in ware washing |
EP3461882A1 (en) | 2013-04-15 | 2019-04-03 | Ecolab USA Inc. | Peroxycarboxylic acid based sanitizing rinse additives for use in ware washing |
WO2015030836A1 (en) | 2013-08-27 | 2015-03-05 | Ecolab Usa Inc. | Solid rinse aid composition and method of making same |
WO2015070119A1 (en) | 2013-11-11 | 2015-05-14 | Ecolab Usa Inc. | Multiuse, enzymatic detergent and methods of stabilizing a use solution |
WO2015070117A1 (en) | 2013-11-11 | 2015-05-14 | Ecolab Usa Inc. | High alkaline warewash detergent with enhanced scale control and soil dispersion |
WO2015073207A1 (en) | 2013-11-14 | 2015-05-21 | Dow Global Technologies Llc | Epoxyamine alkoxylate motor oil dispersants |
WO2015077635A2 (en) | 2013-11-22 | 2015-05-28 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same |
EP4047110A1 (en) | 2014-06-20 | 2022-08-24 | Ecolab USA Inc. | Cip method for cleaning using a non-staining high alkaline cleaner |
US11103118B2 (en) | 2014-08-01 | 2021-08-31 | Ecolab Usa Inc. | Method of manual surface cleaning using cleaning textiles and of washing said cleaning textiles |
WO2016025206A1 (en) | 2014-08-14 | 2016-02-18 | Ecolab Usa Inc. | Polymers for industrial laundry detergents |
WO2016033563A1 (en) | 2014-08-29 | 2016-03-03 | Ecolab Usa Inc. | Solid rinse aid composition comprising polyacrylic acid |
WO2016187307A1 (en) | 2015-05-19 | 2016-11-24 | Ecolab Usa Inc. | Efficient surfactant system on plastic and all types of ware |
WO2016187293A1 (en) | 2015-05-19 | 2016-11-24 | Ecolab Usa Inc. | Efficient surfactant system on plastic and all types of ware |
WO2017011158A1 (en) | 2015-07-14 | 2017-01-19 | Ecolab Usa Inc. | Controlled rate of foam breakage in hard surface cleaners |
EP4219671A2 (en) | 2015-07-14 | 2023-08-02 | Ecolab USA Inc. | Controlled rate of foam breakage in hard surface cleaners |
EP4119641A1 (en) | 2015-07-27 | 2023-01-18 | Ecolab USA Inc. | Dry lubricator for plastic and stainless steel surfaces |
EP3757200A1 (en) | 2015-08-21 | 2020-12-30 | Ecolab USA Inc. | Pyrithione preservative system in solid rinse aid products |
EP3159394A1 (en) | 2015-10-20 | 2017-04-26 | The Procter and Gamble Company | Method of removing stains by treating fabrics with starch and amylase |
EP4219672A2 (en) | 2015-10-28 | 2023-08-02 | Ecolab USA Inc. | Method of using a soil release polymer |
WO2017075384A1 (en) | 2015-10-28 | 2017-05-04 | Ecolab Usa Inc. | Method of using a soil release polymer |
EP4230714A1 (en) | 2015-11-12 | 2023-08-23 | Ecolab USA Inc. | Low-foaming warewash detergent containing mixed cationic/nonionic surfactant system for enhanced oily soil removal |
WO2017100267A1 (en) | 2015-12-08 | 2017-06-15 | Ecolab Usa Inc. | Pressed manual dish detergent |
EP3444327A1 (en) | 2015-12-08 | 2019-02-20 | Ecolab USA Inc. | Pressed manual dish detergent |
US10717106B2 (en) | 2015-12-10 | 2020-07-21 | Ecolab Usa Inc. | Abrasion-masking composition for use with reusable containers and the method of using the same |
WO2017100595A1 (en) | 2015-12-10 | 2017-06-15 | Ecolab Usa Inc. | Abrasion-masking composition for use with reusable containers and the method of using the same |
US9670433B1 (en) | 2015-12-28 | 2017-06-06 | Ecolab Usa Inc. | Hard surface cleaning compositions |
US11254897B2 (en) | 2015-12-28 | 2022-02-22 | Ecolab Usa Inc. | Hard surface cleaning compositions |
US10781400B2 (en) | 2015-12-28 | 2020-09-22 | Ecolab Usa Inc. | Hard surface cleaning compositions |
US10041021B2 (en) | 2015-12-28 | 2018-08-07 | Ecolab Usa Inc. | Hard surface cleaning compositions |
WO2017201404A1 (en) | 2016-05-19 | 2017-11-23 | Ecolab Usa Inc. | Cleaning compositions for use with calcite-based stone |
WO2018013881A1 (en) | 2016-07-15 | 2018-01-18 | Ecolab Usa Inc. | Aluminum safe degreasing and pre-soak technology for bakery and deli wares and use thereof |
WO2018039603A1 (en) | 2016-08-25 | 2018-03-01 | Ecolab Usa Inc. | Cleaning compositions comprising amino acid and methods of use |
WO2018049036A1 (en) | 2016-09-07 | 2018-03-15 | Ecolab Usa Inc. | Detergent compositions containing a stabilized enzyme by phosphonates |
WO2018049029A1 (en) | 2016-09-07 | 2018-03-15 | Ecolab Usa Inc. | Solid detergent compositions and methods of adjusting the dispense rate of solid detergents using solid anionic surfactants |
EP4332208A2 (en) | 2016-09-07 | 2024-03-06 | Ecolab USA Inc. | Detergent compositions containing a stabilized enzyme by phosphonates |
WO2018104221A1 (en) | 2016-12-05 | 2018-06-14 | Covestro Deutschland Ag | Method for producing tdi-based flexible polyurethane foams containing organic acid anhydrides and/or organic acid chlorides |
WO2018104222A1 (en) | 2016-12-05 | 2018-06-14 | Covestro Deutschland Ag | Use of acrylic acid esters and amides for reducing emissions of a polyurethane foam |
EP3336115A1 (en) | 2016-12-19 | 2018-06-20 | Covestro Deutschland AG | Process for the reduction of emissions in polyurethane foams |
WO2018114820A1 (en) | 2016-12-19 | 2018-06-28 | Covestro Deutschland Ag | Method for lowering emissions of a polyurethane foam |
WO2018160879A2 (en) | 2017-03-01 | 2018-09-07 | Polnox Corporation | Macromolecular corrosion (mcin) inhibitors: structures, methods of making and using the same |
WO2018160818A1 (en) | 2017-03-01 | 2018-09-07 | Ecolab Usa Inc. | Reduced inhalation hazard sanitizers and disinfectants via high molecular weight polymers |
EP4043541A1 (en) | 2017-03-01 | 2022-08-17 | Ecolab USA Inc. | Mechanism of urea/solid acid interaction under storage conditions and storage stable solid compositions comprising urea and acid |
WO2018160809A1 (en) | 2017-03-01 | 2018-09-07 | Ecolab Usa Inc. | Mechanism of urea/solid acid interaction under storage conditions and storage stable solid compositions comprising urea and acid |
WO2018208558A1 (en) | 2017-05-11 | 2018-11-15 | Ecolab Usa Inc. | Compositions and method for floor cleaning or restoration |
WO2019067608A1 (en) | 2017-09-27 | 2019-04-04 | Ecolab Usa Inc. | Use of eo/po block copolymer surfactant for controlling viscoelasticity in highly concentrated liquid formulations |
WO2019094418A1 (en) | 2017-11-07 | 2019-05-16 | Ecolab Usa Inc. | Alkaline cleaning composition and methods for removing lipstick |
EP3492503A1 (en) | 2017-11-29 | 2019-06-05 | Covestro Deutschland AG | Polyester containing imide |
WO2019105935A1 (en) | 2017-11-29 | 2019-06-06 | Covestro Deutschland Ag | Imide-containing polyester |
WO2019108990A1 (en) | 2017-12-01 | 2019-06-06 | Ecolab Usa Inc. | Cleaning compositions and methods for removing baked on grease from fryers and other hot surfaces |
WO2019112744A1 (en) | 2017-12-07 | 2019-06-13 | Ecolab Usa Inc. | Compositions and methods for removing lipstick using branched polyamines |
WO2019148076A1 (en) | 2018-01-26 | 2019-08-01 | Ecolab Usa Inc. | Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a binder and optional carrier |
WO2019148090A1 (en) | 2018-01-26 | 2019-08-01 | Ecolab Usa Inc. | Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a carrier |
WO2019148082A1 (en) | 2018-01-26 | 2019-08-01 | Ecolab Usa Inc | Solid cleaning composition |
WO2019148071A1 (en) | 2018-01-26 | 2019-08-01 | Ecolab Usa Inc. | Solidifying liquid anionic surfactants |
WO2019173688A1 (en) | 2018-03-08 | 2019-09-12 | Ecolab Usa Inc. | Solid enzymatic detergent compositions and methods of use and manufacture |
WO2020006346A1 (en) | 2018-06-29 | 2020-01-02 | Ecolab Usa Inc. | Formula design for a solid laundry fabric softener |
WO2020023693A1 (en) | 2018-07-25 | 2020-01-30 | Ecolab Usa Inc. | Rinse aid formulation for cleaning automotive parts |
WO2020086929A1 (en) | 2018-10-26 | 2020-04-30 | Ecolab Usa Inc. | Synergistic surfactant package for cleaning of food and oily soils |
US20220002468A1 (en) * | 2018-11-15 | 2022-01-06 | Ingevity Uk Ltd. | Polyurethane or polyurethane-urea compositions with reduced cold hardening |
WO2020113218A2 (en) | 2018-11-30 | 2020-06-04 | Ecolab Usa Inc. | Surfactant compositions and use thereof |
WO2020159955A1 (en) | 2019-01-29 | 2020-08-06 | Ecolab Usa Inc. | Use of cationic sugar-based compounds as corrosion inhibitors in a water system |
WO2020160429A1 (en) | 2019-01-31 | 2020-08-06 | Ecolab Usa Inc. | Controller for a rinse water reuse system and methods of use |
WO2020160396A1 (en) | 2019-01-31 | 2020-08-06 | Ecolab Usa Inc. | Rinse water reuse system and methods of use |
WO2020160390A1 (en) | 2019-01-31 | 2020-08-06 | Ecolab Usa Inc. | Laundry machine kit to enable control of water levels, recirculation, and spray of chemistry |
WO2020160425A1 (en) | 2019-01-31 | 2020-08-06 | Ecolab Usa Inc. | Controlling water levels and detergent concentration in a wash cycle |
WO2020181159A1 (en) | 2019-03-06 | 2020-09-10 | Ecolab Usa Inc. | Concentrated solid hard surface cleaner |
WO2020236873A1 (en) | 2019-05-20 | 2020-11-26 | Ecolab Usa Inc. | Surfactant package for high foaming detergents with low level of medium to long chain linear alcohols |
WO2020257749A1 (en) | 2019-06-21 | 2020-12-24 | Ecolab Usa Inc. | Solid nonionic surfactant compositions |
WO2020264236A1 (en) | 2019-06-28 | 2020-12-30 | Ecolab Usa Inc. | Concentrated solid laundry softener composition |
WO2021022045A1 (en) | 2019-07-31 | 2021-02-04 | Ecolab Usa Inc. | Personal protective equipment free delimer compositions |
WO2021046285A1 (en) | 2019-09-06 | 2021-03-11 | Ecolab Usa Inc. | Concentrated surfactant systems for rinse aid and other applications |
WO2021067407A1 (en) | 2019-09-30 | 2021-04-08 | Ecolab Usa Inc. | Stabilized enzymatic detergent compositions |
WO2021163407A1 (en) | 2020-02-12 | 2021-08-19 | Ecolab Usa Inc. | Use of urea or a urea / chelator combination to chemically stabilize peroxycarboxylic acid and peroxide formulations |
WO2021183990A2 (en) | 2020-03-13 | 2021-09-16 | Harpe Bioherbicide Solutions, Inc. | Herbicidal mentha plant extract compositions and methods of using same |
WO2021195015A1 (en) | 2020-03-23 | 2021-09-30 | Ecolab Usa Inc. | Novel 2-in-1 sanitizing and rinse aid compositions employing amine based surfactants in machine warewashing |
WO2021222510A1 (en) | 2020-04-30 | 2021-11-04 | Ecolab Usa Inc. | Low foam cleaning compositions |
WO2021222675A1 (en) | 2020-04-30 | 2021-11-04 | Ecolab Usa Inc. | Quaternary ammonium sanitizing composition |
WO2021247814A1 (en) | 2020-06-03 | 2021-12-09 | Ecolab Usa Inc. | Non-caustic cleaning methods and uses |
WO2022140518A1 (en) | 2020-12-23 | 2022-06-30 | Ecolab Usa Inc. | Non-cationic softeners and methods of use |
WO2022140505A1 (en) | 2020-12-23 | 2022-06-30 | Ecolab Usa Inc. | Soil removal on cotton via treatment in the rinse step for enhanced cleaning in the subsequent wash |
WO2022140522A1 (en) | 2020-12-23 | 2022-06-30 | Ecolab Usa Inc. | Laundry sour softener with extra stability and additional benefits of laundry fire mitigation and sunscreen removal |
WO2022221670A2 (en) | 2021-04-15 | 2022-10-20 | Ecolab Usa Inc. | Enzymatic floor cleaning composition |
EP4116397A1 (en) | 2021-07-06 | 2023-01-11 | The Procter & Gamble Company | Whitening additive |
WO2023283208A1 (en) | 2021-07-06 | 2023-01-12 | The Procter & Gamble Company | Whitening additive |
WO2023076669A1 (en) | 2021-10-29 | 2023-05-04 | Ecolab Usa Inc. | No rinse quaternary ammonium disinfectant composition for food contact surfaces |
WO2023087194A1 (en) | 2021-11-18 | 2023-05-25 | Ecolab Usa Inc. | Manual detergent for pot and pan with destaining function |
WO2023087195A1 (en) | 2021-11-18 | 2023-05-25 | Ecolab Usa Inc. | Fast drying multi-purpose cleaning and disinfecting compositions and methods of their use |
WO2023122196A1 (en) | 2021-12-22 | 2023-06-29 | Ecolab Usa Inc. | Compositions comprising multiple charged cationic compounds for soil release |
WO2023141490A1 (en) | 2022-01-19 | 2023-07-27 | Ecolab Usa Inc. | Non-fluorocarbon laundry treatment providing enhanced fluid repellency |
WO2023197233A1 (en) | 2022-04-14 | 2023-10-19 | Ecolab Usa Inc. | Chemo-mechanical solution for cleaning fluidic tanks and piping |
WO2023201319A1 (en) | 2022-04-15 | 2023-10-19 | Ecolab Usa Inc. | Ppe-free tablet degreaser and multipurpose cleaner |
WO2023225624A1 (en) | 2022-05-20 | 2023-11-23 | Ecolab Usa Inc. | Neutral solid and liquid enzymatic rinse aid |
WO2024000340A1 (en) | 2022-06-30 | 2024-01-04 | Ecolab Usa Inc. | Non-silicated metal protectant pressed alkaline detergent and rinse additive |
WO2024031514A1 (en) | 2022-08-11 | 2024-02-15 | Ecolab Usa Inc. | A multipurpose liquid rinse aid |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2674619A (en) | Polyoxyalkylene compounds | |
US2677700A (en) | Polyoxyalkylene surface active agents | |
US3101374A (en) | Polyoxyalkylene surface active agents having heteric polyoxyethylene solubilizing chains | |
US3022335A (en) | Surface active polyoxyalkylene compounds having a plurality of heteric polyoxypropylene-polyoxyethylene chains | |
US2213477A (en) | Glycol and polyglycol ethers of isocyclic hydroxyl compounds | |
US2454541A (en) | Polymeric detergents | |
US3829506A (en) | Biodegradable surface active agents having good foam properties and foam stabilizing characteristics | |
US3928213A (en) | Fabric softener and soil-release composition and method | |
EP0656048B1 (en) | Liquid softener composition | |
US3899387A (en) | Process of making paper using mono-isocyanate capped poly (oxyalkylene) diols as a re-wetting and defoaming agent | |
CA2077349C (en) | Castable fluid tenside concentrate | |
CH626395A5 (en) | ||
GB1601652A (en) | Liquid detergents comprising nonionic surfactants | |
US2355823A (en) | Polyglycol ethers of higher second | |
US3457203A (en) | Hydrophilic polyurethane foams and a process for preparing them | |
US4215026A (en) | Aqueous dispersion of a branched polyester | |
US4038296A (en) | Alkylene oxide derivatives based on polytetrahydrofuran copolymers | |
US2224293A (en) | Method of treating fabrics and other materials | |
US3203955A (en) | Surface active mixtures of polyoxyalkylene compounds having a single heteric polyoxypropylene-polyoxyethylene chain | |
CA1227715A (en) | Foam control | |
CN115216961B (en) | Biological-based all-in-one textile scouring agent and preparation method and application thereof | |
US4268410A (en) | Polyether polyester surfactants, their production and uses | |
US3959229A (en) | Textile treatments | |
US4339236A (en) | Low foam scouring agents | |
US3354089A (en) | Windshield wipers |