US2950253A - Methods of washing textile fabrics - Google Patents
Methods of washing textile fabrics Download PDFInfo
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- US2950253A US2950253A US446146A US44614654A US2950253A US 2950253 A US2950253 A US 2950253A US 446146 A US446146 A US 446146A US 44614654 A US44614654 A US 44614654A US 2950253 A US2950253 A US 2950253A
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- 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
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- 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
- C11D1/02—Anionic compounds
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- 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
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
- D06L1/12—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using aqueous solvents
- D06L1/16—Multi-step processes
Definitions
- This invention relates to a method of laundering textile fabrics and to a composition of matter for laundering such fabrics more efficiently.
- Cation-active compounds which, when present in sufficient concentration, are suitable for use in connection with our invention are cation-active onium compounds, such as, for example, ammonium, sulfonium, phosphoniurn and like compounds. While, in general, any cation-active onium compound is a suitable additive for the purpose of charging the fiber and soil with a positive charge, those onium compounds comprising at least one high-molecular hydrocarbon radical with at least 6 and no more than 20 carbon atoms in its molecule are preferred.
- the hydrocarbon radical may also contain heteroatoms, heteroatom groups or substituents.
- onium compounds are the following, which are derived from ammonia or organic nitrogen compounds:
- Trimethyl-hexyl-ammonium chloride Trimethyl-dodecylammonium chloride Trimethyl-octadecylammonium methosulfate Dimethyl-dodecyl-benzyl-ammonium chloride Hexylpyridinium-bisulfate Octadecylpyridinium chloride Hexylquinolinium chloride
- suitable onium compounds are the following in which one or more of the alkyl radicals contain heteroatoms or heteroatom groups:
- Octadecoxy-carbomethyl-trimethyl-ammonium chloride Dodecoxy-carbomethyl-pyridinium-methosulfate Naphthenoxy-carbomethyl-quinolinium chloride Abietyloxy-carbomethyl-quinolinium bromide Di(dodecoxy-carbomethyl)-dimethyl-ammonium methosulfate Octadecyl-amino-carbomethyl-trimethyl-ammonium chloride Octadecyl-anilino-carbomethyl-pyridinium-bisulfate Dodecoxymethyl-trimethyl-ammonium chloride Octadecylthiomethyl-triethyl-ammonium bisulfate Octadecyl-carbaminomethyl-pyridinium chloride Octadecyloxy-carbaminomethyl-pyridinium-methosulfate and the like, as well as the corresponding compounds containing a quaternary phosphorus atom or
- the effect of placing a positive electrical charge upon the fiber and the soil can be enhanced by the additional and simultaneous use of other types of cation-active compounds such as, for example, acid salts or acids, which adjust the pH of the washing solution to acid reaction, or of easily absorbable multivalent cationic compounds such as, for example, salts of aluminum and the like.
- cation-active compounds such as, for example, acid salts or acids, which adjust the pH of the washing solution to acid reaction, or of easily absorbable multivalent cationic compounds such as, for example, salts of aluminum and the like.
- Compounds suitable for use in accordance with our invention to augment the effect of low-concentration solutions of onium compounds by changing the pH of such solutions to acid reaction include inorganic and organic acids such as, for example, hydrochloric acid, sulfuric acid, phosphoric acid, boric acid, formic acid, acetic acid, lactic acid and adipic acid, as well as acid salts such as, for example, bisulfates, monophosphates, monocitrates and the like.
- Multivalent cation c. compounds which are suitable to augment the electrical charging effect of low-concentration solutions of onium compounds,includeinorganicand organic salts of aluminum, such as, for example, aluminum sulfate, lactate and aluminum formate, as .well as salts of other polyvalent metals or also, salts ofpolyvalent organic bases.
- H I 1 The amounts ofadditives which will produce the desired effect of charging the fiber and the soil with'a positive electrical charge. dependlargely upon the type of fiber, upon the nature and reaction of the, soil, upon the volume of washing solution and, last-but by no means least, also upon the co position of the cationic additives, particularly the cationic washing agent.
- the proper amount ofcation-active additive can'be most easily determined by the laundering results, but it may also be determined at anytirneduringthe laundering process by flocculation tests or by electrorkinetic test.
- the washing solution is provided with cation-active agents such as the onium compounds described above and, if necessary, the above-described agents which augment the positive electrical charging effect of the cation-active agents on the fiber and the soil.
- this Washing solution is provided with an additive comprising cationic colloids whereby the positive electrical charging eflt'ect is still further augmented.
- l i T Cationic colloids which are suitable for this purpose accordance with ouriinvention include high-molecular, oxygen-containing compounds such as polyalcohols, polyetheralcohols or polyethers and their derivatives.
- Such'colloids are'alkylcelluloses, such as oxyethylcellulose, as well as corresponding starch derivatives, chitoseamines, polyalkyleneoxides, such as polyalkyleneoxide waxes,'and the like.
- i s v These cationic colloids are added to the washingsolution in amounts ranging from 0.01 to 0.5 gm/liter, depending upon the composition of the washing solution and the operating conditions. 7 a
- the number and sequence ofthe anion-active and cation-active washing solutions can'be varied between wide limits, depending upon the amountand nature of the soil and the types of fibers the'batch of laundry to be washed. u rk
- This multiple-bath washing method is applicable to all types of textile fabrics including cotton, artificial wool, linen, natural wool, rayon, natural silk, as well as all types of synthetic fibers. It is particularly well-adapted for washing fabrics made of synthetic fibers the cleansing of which has been found to present much greater difiiculties than originally anticipated.
- Anion-active washing agents suitable to be added to the washing solution to impart a negative electrical charge to the fiber and the soil in the multiple-bath method include all of the well-known washing agents, such as soaps, alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, and the like.
- Cation-active washing agents suitable to be added to the washing solution to impart a positive electrical charge to the fiber and the soil in our multiple-bath method include all of the onium compounds disclosed above in connection with the single-bath methods.
- the positive electrical charging elfect upon fiber and soil may be augmented by the addition of organic and inorganic acids and acid salts, polyvalent metal salts and cationic colloids. 1
- the washing solution employed in the washing process in accordance withour invention may at the same time contain any of the well-known non-ionic, surface-active compounds. They include, for example, alkyleneoxide addition products of higher molecular alcohols, amines,
- Example I clohexyl-dimethylammonium chloride and '1 gm./liter acetic acid at 40 C. and at a pH of about 3, then rinsed, spin-dried and finally air-dried. The undergarments were clean and pure white. 7
- Example III fMens white shirts made of terephthalic acid ethyleneglycol polyester fibers (Dacron) were soaked for half an hour at 40? C. in an aqueous bath which contained 0.5 gm./ liter hexade coxy carbomethyl trimethyl ammonium chloride, 0.5 gm./liter aluminum formate and 0.5 gm./liter formic acid.
- the pH of the bath was about 3.
- the shirts were then washed in this solution with moderate rubbing, and when necessary the highly soiled edges of the collar and the cuffs were treated with a concentrated solution of the cation-active washing agent.
- the s s we efin n fid n s riedi ihe sualmanner.
- Example 1V Mens colored socks made of polyacrylic nitrile fibers (Orlon) were vigorously washed in an aqueous bath which contained 0.4 gm./1iter octadecyl-trimethyl-ammoniumbisulfate, 0.2 gm./liter of a condensation product of 1 mol octylphenol and about 9 mols ethyleneoxide, and 0.5 gm./liter acetic acid, the bath being at a temperature of about 30 C. and its pH being about 4. Soil and perspiration, as well as soil and color stains originating from the shoes, which are common with synthetic fibers, were completely removed from the socks.
- Example V Women white blouses made of polyamide fibers (nylon) were washed in an aqueous bath at 4050 C.
- the bath contained 0.4 gm./ liter octadecoxy-carbomethyl-trimethyb ammonium chloride, 1 gm./ liter acetic acid and 0.03 gin/liter methyl-cellulose.
- the blouses were absolutely clean when removed from the bath and they did not turn
- Example VI Colored patterned sweaters made of wool were washed at 30 C.
- Example VII Twelve colored nightgowns made of polyamide fibers (Perlon) were washed at 25 C. in an aqueous solution which contained 0.3 gm./liter tetradecoXy-carbomethyltrimethyl-ammonium chloride, 0.2 gm./ liter of condensation products of 1 mol. dodecylalcohol and about 10 mols ethyleneoxide, 0.5 gm./liter acetic acid and 0.05 gm./ liter oxyethylenecellulose.
- the nightgowns were absolutely clean, the weave showed up very clearly, the material was soft to the touch, and the colors were clear and bright.
- Example 1X Mens white shirts made of polyamide fibers (nylon) which had been worn for a long time without washing were Washed for minutes at increasing temperatures from to 60 C. in a drum-type washing machine, holding a washing solution containing 1.2 gm./liter sodiumdodecyl benzene sulfonate and 0.5 gm./liter sodium tripolyphosphate. The solution was then drained oi, the goods were rinsed, and subsequently subjected to a second washing run at 50 C. for 15 minutes in a solution containing 0.5 gm./liter heXadecyltrimethyl-ammonium chloride and 1 grn./liter acetic acid. The goods were found to be clean without spot-cleaning.
- the method of cleansing a soiled synthetic textile fabric which comprises washing said fabric in a cationactive aqueous solution consisting essentially of water and from about 0.85 to about 1.5 gm./ liter of a cationactive washing composition
- a cationactive washing composition comprising (1) from about 23% to about 44% of an organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, (2) from
- the method of cleansing a soiled synthetic textile fabric which comprises washing said fabric at least once in a cation-active aqueous solution consisting essentially of Water and from about 0.85 to about 1.5 gm./liter of a cation-active washing composition
- a cation-active washing composition comprising (1) from about 23 to about 44% of an organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radica s having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20
- the method of cleansing a soiled synthetic textile fabric which comprises washing said fabric in a cationactive aqueous solution consisting of water, from about 0.3 to about 0.5 gm./liter of a cation-active organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached alkanoic acid.
- the method of cleansing a soiled synthetic textile fabric 'which'comprises washing said fabric in a cationactive aqueous Solution consisting of water, from about 0.3 to about 0.5 gm./liter of a cation-active organic oniumtcompound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected horn the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having
- the method of cleansing a soiled synthetic textile fabric which comprises washing said fabric in a cationactive aqueous solution consisting of water, from about 0.3 to about 0.5 gm./liter of a cation-active organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom analiphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, from about 0.5 to about 1.0 gm./liter of a lower alkanoic acid and from 0.01 to
- a composition of matter for cleansing soilecl synthetic textile fabrics consisting essentially of water and from about 0.85 to about 1.5 gm./liter of a cation-active washing composition
- a cation-active washing composition comprising (1) from about 23% to about 44% of an organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having'attached to the nitrogen atom analiphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, (2) from about 33% to about 77% of a lower alkan
- a composition of matter for cleansing soiled synthetic textile fabrics consisting essentially of water, from about 0.3 to about 0.5 gm./ liter of a cation-active organic onium compound'selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen-atom analiphatic radical containing a hydrocarbon chainhaving from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to Q carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, and from about 0.5 to about 1.0 gm./liter of a lower alkanoic acid.
- a composition of matter for cleansing soiled synthetic textile fabrics consisting essentially of water, from about 0.3 to about 0.5 gm./liter of a cation-active organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to 'the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom' an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, from about 0.5 to about 1.0 gm./liter of a lower alkanoic acid, and about 0.5 g
- a composition of matter for cleansing soiled synthetic textile fabrics consisting essentially of water, from about 0.3 to about 0.5 gm./ liter of a cation-active organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, from about 0.5 to about -1.0 gm./liter of a lower alkanoic acid, and from about 0.01 to 0.5 gm./liter of an additive
- the method of cleansing a soiled polyamide fiber fabric which comprises washing said fabric in a cationactive aqueous solution consisting essentially of water and from about 0.85 to about 1.5 gm./liter of a cationactive washing composition
- a cationactive washing composition comprising (1) from about 23% to about 44% of an organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain havingfrom 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl, and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain havingfrom 6 to 20 carbon atoms, (2)
Description
METHODS OF WASHING TEXTILE FABRIECS Walter Kling and Hermann Lange, Dusseldorf, Germany, assignors to Bohrne Fettchemie 'G.m.b.H., Dusseldorf, Germany, a corporation of Germany No Drawing. Filed July 27, 1%54, Ser. No. 446,146
Claims priority, application Germany July 29, 1953 Claims. (Cl. 252-152) This invention relates to a method of laundering textile fabrics and to a composition of matter for laundering such fabrics more efficiently.
It is well known that heavily soiled fabrics of all types are diflicult to launder to absolute cleanliness with ordinary Washing agents such as laundry soaps and detergents, particularly if the soiling substance is of a fatty nature or contains dyes. Practical experience has also shown that this is also true of soiled synthetic fabrics such as nylon, Perlon, Orlon, Dacron and others, despite the fact that the opinion has often been expressed in the literature that such synthetic fibers are particularly easy to cleanse. Moreover, synthetic fabrics have a tendency to undergo a gray or brownish discoloration after only a few times of laundering with the Washing agents now generally in use. This discoloration becomes more accentuated in varying degrees in places upon the fabric which are subjected to heavy wear and perspiration, such as, for example, the armpits, cuffs and the collars of shirts, blouses, jackets and the like.
It is an object of the present invention to provide a method of laundering soiled fabrics of all types which will completely remove the soiling substance from the fabric.
It is another object of this invention to provide a composition of matter for laundering fabrics which, when added to the washing solution, will aid in completely ridding soiled fabrics of all types of soil without any special manipulation of the fabric in the washing solution.
We have found that good laundering results can be obtained if both the fiber and the soil are charged with a positive electrical charge during the washing operation by adding a sufficient amount of a cation-active substance to the washing solution.
It is well known in the art that in ordinary laundering processes with the usual anion-active substances the fiber and the soil have a negative charge imparted thereto. It is generally believed in the art that the electrostatic repulsion created thereby between the fiber and the soil contributes considerably to the removal of the soil. It is further known that cation-active substances added to the washing solution in insufficient quantities have a negative cleansing eifect; i.e., they effect an increased attraction between the fiber and the soiling substance.
We have surprisingly discovered that in laundering fabrics composed entirely of synthetic fibers, such as, for example, polyester fibers, polyamide fibers, polyisocyanate fibers, fibers made from vinylpolymerisates such as polyvinylchloride, polyvinylacetate and the like, fibers made from polymerisates of acrylic acid derivatives such as 2,959,253 Patented Aug. 23, 1960 "ice acrylic acid esters, acrylic acid nitriles and the like, it is possible to remove all types of soil and obtain a perfectly clean fabric if the washing solution contains a sufficient amount, per unit volume of solution, of at least one cation-active substance to impart a positive charge to the soil and the fabric.
Cation-active compounds which, when present in sufficient concentration, are suitable for use in connection with our invention are cation-active onium compounds, such as, for example, ammonium, sulfonium, phosphoniurn and like compounds. While, in general, any cation-active onium compound is a suitable additive for the purpose of charging the fiber and soil with a positive charge, those onium compounds comprising at least one high-molecular hydrocarbon radical with at least 6 and no more than 20 carbon atoms in its molecule are preferred. The hydrocarbon radical may also contain heteroatoms, heteroatom groups or substituents.
Specific examples of suitable onium compounds are the following, which are derived from ammonia or organic nitrogen compounds:
Trimethyl-hexyl-ammonium chloride Trimethyl-dodecylammonium chloride Trimethyl-octadecylammonium methosulfate Dimethyl-dodecyl-benzyl-ammonium chloride Hexylpyridinium-bisulfate Octadecylpyridinium chloride Hexylquinolinium chloride Other examples of suitable onium compounds are the following in which one or more of the alkyl radicals contain heteroatoms or heteroatom groups:
Octadecoxy-carbomethyl-trimethyl-ammonium chloride Dodecoxy-carbomethyl-pyridinium-methosulfate Naphthenoxy-carbomethyl-quinolinium chloride Abietyloxy-carbomethyl-quinolinium bromide Di(dodecoxy-carbomethyl)-dimethyl-ammonium methosulfate Octadecyl-amino-carbomethyl-trimethyl-ammonium chloride Octadecyl-anilino-carbomethyl-pyridinium-bisulfate Dodecoxymethyl-trimethyl-ammonium chloride Octadecylthiomethyl-triethyl-ammonium bisulfate Octadecyl-carbaminomethyl-pyridinium chloride Octadecyloxy-carbaminomethyl-pyridinium-methosulfate and the like, as well as the corresponding compounds containing a quaternary phosphorus atom or arsenic atom, or a tertiary sulfur atom, such as, for example dimethyl dioctyl phosphonium chloride, trimethyl dodecyl phosphonium sufiate, triethyl octadecyl phosphoniurn chloride ad the like as well as the corresponding alkyl arsonium or alkyl stibonium salts respectively, dimethyl dodecyl sulfonium chloride, dimethyl octadecyl sulfonium methosulfate and the like.
If, for economic reasons, it is necessary to carry out our method of laundering with low concentrations of cation-active substances in the washing solution, the effect of placing a positive electrical charge upon the fiber and the soil can be enhanced by the additional and simultaneous use of other types of cation-active compounds such as, for example, acid salts or acids, which adjust the pH of the washing solution to acid reaction, or of easily absorbable multivalent cationic compounds such as, for example, salts of aluminum and the like.
Compounds suitable for use in accordance with our invention to augment the effect of low-concentration solutions of onium compounds by changing the pH of such solutions to acid reaction include inorganic and organic acids such as, for example, hydrochloric acid, sulfuric acid, phosphoric acid, boric acid, formic acid, acetic acid, lactic acid and adipic acid, as well as acid salts such as, for example, bisulfates, monophosphates, monocitrates and the like.
. Multivalent cation c. compounds. which are suitable to augment the electrical charging effect of low-concentration solutions of onium compounds,includeinorganicand organic salts of aluminum, such as, for example, aluminum sulfate, lactate and aluminum formate, as .well as salts of other polyvalent metals or also, salts ofpolyvalent organic bases. H I 1 The amounts ofadditives which will produce the desired effect of charging the fiber and the soil with'a positive electrical charge. dependlargely upon the type of fiber, upon the nature and reaction of the, soil, upon the volume of washing solution and, last-but by no means least, also upon the co position of the cationic additives, particularly the cationic washing agent.
The proper amount ofcation-active additive can'be most easily determined by the laundering results, but it may also be determined at anytirneduringthe laundering process by flocculation tests or by electrorkinetic test.
While we have thus far described a method of laundering synethic fabrics, the general concept of our invention, namely to provide the fiberand thesoil with a positive electrical charge during at least a portion of the washing operation, can be applied to textile fibers in general regardless of the type of fiber of which such fabrics are composed.
Thus, for example, if a batch of soiled laundry con taius fabrics made of both synthetic and natural fibers, the washing solution is provided with cation-active agents such as the onium compounds described above and, if necessary, the above-described agents which augment the positive electrical charging effect of the cation-active agents on the fiber and the soil. In addition, this Washing solution is provided with an additive comprising cationic colloids whereby the positive electrical charging eflt'ect is still further augmented. l i T Cationic colloids which are suitable for this purpose accordance with ouriinvention include high-molecular, oxygen-containing compounds such as polyalcohols, polyetheralcohols or polyethers and their derivatives. Examples of such'colloids are'alkylcelluloses, such as oxyethylcellulose, as well as corresponding starch derivatives, chitoseamines, polyalkyleneoxides, such as polyalkyleneoxide waxes,'and the like. i s v These cationic colloids are added to the washingsolution in amounts ranging from 0.01 to 0.5 gm/liter, depending upon the composition of the washing solution and the operating conditions. 7 a
If the fabrics to be laundered'are veryheavily soiled, it is advantageous to employ a multiple-bath washing process wherein the individual washing solutionshave approximately the same composition *asintheabovedescribed single-bath process. a
We have found that improved laundering results are obtained if the heavily soiled fabrics are subjected to a multiple-bath washing process in which at least one solution charges the fiber and the soil negatively and at least one solution charges .the fiber and the soil positively. in other words, the fabrics to be laundered are washedpart of the time in an anion-active washing solution and part of the time in a cation-active washing solution. I
The number and sequence ofthe anion-active and cation-active washing solutions can'be varied between wide limits, depending upon the amountand nature of the soil and the types of fibers the'batch of laundry to be washed. u rk This multiple-bath washing method is applicable to all types of textile fabrics including cotton, artificial wool, linen, natural wool, rayon, natural silk, as well as all types of synthetic fibers. It is particularly well-adapted for washing fabrics made of synthetic fibers the cleansing of which has been found to present much greater difiiculties than originally anticipated.
Anion-active washing agents suitable to be added to the washing solution to impart a negative electrical charge to the fiber and the soil in the multiple-bath method include all of the well-known washing agents, such as soaps, alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, and the like. a
Cation-active washing agents suitable to be added to the washing solution to impart a positive electrical charge to the fiber and the soil in our multiple-bath method include all of the onium compounds disclosed above in connection with the single-bath methods. As in the singlebath methods, the positive electrical charging elfect upon fiber and soil may be augmented by the addition of organic and inorganic acids and acid salts, polyvalent metal salts and cationic colloids. 1
The washing solution employed in the washing process in accordance withour invention may at the same time contain any of the well-known non-ionic, surface-active compounds. They include, for example, alkyleneoxide addition products of higher molecular alcohols, amines,
mercaptans, carboxylic acids, sulfonic acids or their amides, particularly the addition products of ethyleneoxide; also the esterification products of higher molecular carboxylic acids or the etherification products of higher molecular alcohols withpolyethyleneoxide condensates, and the esterification products of higher molecular carboxylic acids or the etherification products of higher molecular alcohols with polyalcohols or polyetheralcohols, such as, for example,,polyglycerines, pentaerythritol, sorbitol, sugars and the like. The use of such compounds in conjunction with the cation-active compounds disclosed above further improves the washing results obtained, particularly if the soil is of a fatty nature; v
'The following examples will enable persons skilled in the art to understand our invention more completely. However, it is understood that our invention is not limited to the conditions, quantities and specific compounds disclosed in these examples.
r Example I Ladies brown stockings made of polyamide fibers (Perlon) were washed at 35 C. in an aqueous bath which contained 1.2 gmJliter tetradecyl-pyridiniumbromide. The weight ratio of washable goods to aqueous bath was 1:50, and the pH of the bath was about 7. The stockings were very satisfactorily cleansed.
Example I] clohexyl-dimethylammonium chloride and '1 gm./liter acetic acid at 40 C. and at a pH of about 3, then rinsed, spin-dried and finally air-dried. The undergarments were clean and pure white. 7
' Example III fMens white shirts made of terephthalic acid ethyleneglycol polyester fibers (Dacron) were soaked for half an hour at 40? C. in an aqueous bath which contained 0.5 gm./ liter hexade coxy carbomethyl trimethyl ammonium chloride, 0.5 gm./liter aluminum formate and 0.5 gm./liter formic acid. The pH of the bathwas about 3. The shirts were then washed in this solution with moderate rubbing, and when necessary the highly soiled edges of the collar and the cuffs were treated with a concentrated solution of the cation-active washing agent. The s s we efin n fid n s riedi ihe sualmanner.
The soil was completely removed and the material did not turn gray.
Example 1V Mens colored socks made of polyacrylic nitrile fibers (Orlon) were vigorously washed in an aqueous bath which contained 0.4 gm./1iter octadecyl-trimethyl-ammoniumbisulfate, 0.2 gm./liter of a condensation product of 1 mol octylphenol and about 9 mols ethyleneoxide, and 0.5 gm./liter acetic acid, the bath being at a temperature of about 30 C. and its pH being about 4. Soil and perspiration, as well as soil and color stains originating from the shoes, which are common with synthetic fibers, were completely removed from the socks.
Example V Ladies white blouses made of polyamide fibers (nylon) were washed in an aqueous bath at 4050 C. The bath contained 0.4 gm./ liter octadecoxy-carbomethyl-trimethyb ammonium chloride, 1 gm./ liter acetic acid and 0.03 gin/liter methyl-cellulose. The blouses were absolutely clean when removed from the bath and they did not turn Example VI Colored patterned sweaters made of wool were washed at 30 C. in an aqueous bath which contained 1.5 gm./ liter tetradecylpyridinium bisulfate and 0.1 gm./ liter chitoseamine (produced by alkaline degradation of chitin and subsequent neutralization with acetic acid). The sweaters were very clean, the colors Were bright and the patterns were clear.
Example VII Ladies colored nightgowns made of polyamide fibers (Perlon) were washed at 25 C. in an aqueous solution which contained 0.3 gm./liter tetradecoXy-carbomethyltrimethyl-ammonium chloride, 0.2 gm./ liter of condensation products of 1 mol. dodecylalcohol and about 10 mols ethyleneoxide, 0.5 gm./liter acetic acid and 0.05 gm./ liter oxyethylenecellulose. The nightgowns were absolutely clean, the weave showed up very clearly, the material was soft to the touch, and the colors were clear and bright.
Example VIII Woolen goods, highly soiled with dust, soot and mineral oil, were washed for half an hour at 40 C. in a paddletype washing machine with a washing solution containing 0.6 gm./ liter octadecoxy carbomethyl cyclohexyl dimethyl-ammonium chloride, 1 gm./liter acetic acid and 0.03 gm./ liter methylcellulose. The washing solution was then drained off and the goods were rinsed. Subsequently, the goods were washed for about one hour at the same temperature in another bath containing 1 gm./liter sodium lauryl sulfate and 1 grn./liter sodium carbonate. The washed goods were clean, odorless and the fiber efiects were clear.
Example 1X Mens white shirts made of polyamide fibers (nylon) which had been worn for a long time without washing were Washed for minutes at increasing temperatures from to 60 C. in a drum-type washing machine, holding a washing solution containing 1.2 gm./liter sodiumdodecyl benzene sulfonate and 0.5 gm./liter sodium tripolyphosphate. The solution was then drained oi, the goods were rinsed, and subsequently subjected to a second washing run at 50 C. for 15 minutes in a solution containing 0.5 gm./liter heXadecyltrimethyl-ammonium chloride and 1 grn./liter acetic acid. The goods were found to be clean without spot-cleaning.
While we have given specific examples for practicing our invention, we wish it to be understood that various modifications and changes can be made in the method of practicing our invention, and the quantities and conditions 6 disclosed herein, without departing from the spirit of our invention and the scope of the following claims.
We claim:
1. The method of cleansing a soiled synthetic textile fabric, which comprises washing said fabric in a cationactive aqueous solution consisting essentially of water and from about 0.85 to about 1.5 gm./ liter of a cationactive washing composition comprising (1) from about 23% to about 44% of an organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, (2) from about 33% to about 77% of a lower alkanoic acid and (3) from about 0% to about 33% of an additive stable in said cationic active aqueous solution selected from the group consisting of aluminum salts of lower alkanoic acids, lower alkoxy celluloses, chitoseamine and polyalkylene oxide waxes, whereby both the fabric and the soil are imparted with a positive electrostatic charge and the soil is separated from the fabric by electrostatic repulsion and dispersed throughout the washing solution.
2. The method of cleansing a soiled synthetic textile fabric, which comprises washing said fabric at least once in a cation-active aqueous solution consisting essentially of Water and from about 0.85 to about 1.5 gm./liter of a cation-active washing composition comprising (1) from about 23 to about 44% of an organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radica s having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, (2) from about 33% to about 77% of a lower alkanoic acid and, (3) from about 0% to about 33% of an additive stable in said cationic active aqueous solution selected from the group consisting of aluminum salts of lower alkanoic acids, lower alkoxy celluloses, chitoseamine and polyalkylene oxide waxes, whereby both the fabric and the soil are imparted with a positive electrostatic charge and the soil is separated from the fabric by electrostatic repulsion and dispersed throughout the washing solution, and at least once in an anion-active aqueous solution capable of imparting a negative electrostatic charge to the fabric and the soil.
3. The method of cleansing a soiled synthetic textile fabric, which comprises washing said fabric in a cationactive aqueous solution consisting of water, from about 0.3 to about 0.5 gm./liter of a cation-active organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached alkanoic acid. 7
to thenitrogen atoman aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, and from about 0.5 to about 1.0 gm./liter of a lower 4. The method of cleansing a soiled synthetic textile fabric, 'which'comprises washing said fabric in a cationactive aqueous Solution consisting of water, from about 0.3 to about 0.5 gm./liter of a cation-active organic oniumtcompound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected horn the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, from about 0.5 to about 1.0 gm./liter of a lower alkanoic acid, and about 0.5 gm./liter of an aluminum salt of a lower alkanoic acid.
5. The method of cleansing a soiled synthetic textile fabric, which comprises washing said fabric in a cationactive aqueous solution consisting of water, from about 0.3 to about 0.5 gm./liter of a cation-active organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom analiphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, from about 0.5 to about 1.0 gm./liter of a lower alkanoic acid and from 0.01 to 0.5 gm./liter of an additive stable in said'cationic active aqueous solution selected from the group consisting of aluminum salts of lower alkanoic acids, lower alkoxy celluloses, chitoseamine and polyalkylene oxide waxes. H
6. A composition of matter for cleansing soilecl synthetic textile fabrics consisting essentially of water and from about 0.85 to about 1.5 gm./liter of a cation-active washing composition comprising (1) from about 23% to about 44% of an organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having'attached to the nitrogen atom analiphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, (2) from about 33% to about 77% of a lower alkanoic acid and, (3) from about to about 33% of an additive stable in said cationic active aqueous solution selected from the group consistingof aluminum salts of lower alkanoic acids, lower alkoxy celluloses, chitoseamine and polyalkylene oxide waxes.
7. A composition of matter for cleansing soiled synthetic textile fabrics consisting essentially of water, from about 0.3 to about 0.5 gm./ liter of a cation-active organic onium compound'selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen-atom analiphatic radical containing a hydrocarbon chainhaving from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to Q carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, and from about 0.5 to about 1.0 gm./liter of a lower alkanoic acid. V .7 v v a 8. A composition of matter for cleansing soiled synthetic textile fabrics consisting essentially of water, from about 0.3 to about 0.5 gm./liter of a cation-active organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to 'the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom' an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, from about 0.5 to about 1.0 gm./liter of a lower alkanoic acid, and about 0.5 gm./liter of an aluminum salt of a lower alkanoic acid. a
9. A composition of matter for cleansing soiled synthetic textile fabrics consisting essentially of water, from about 0.3 to about 0.5 gm./ liter of a cation-active organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms, from about 0.5 to about -1.0 gm./liter of a lower alkanoic acid, and from about 0.01 to 0.5 gm./liter of an additive stable in said cationic active aqueous solution selected from the group consisting of aluminum salts of lower alkanoic acids, lower alkoxy celluloses, chitoseamine and polyalkylene oxide waxes.
10. The method of cleansing a soiled polyamide fiber fabric, which comprises washing said fabric in a cationactive aqueous solution consisting essentially of water and from about 0.85 to about 1.5 gm./liter of a cationactive washing composition comprising (1) from about 23% to about 44% of an organic onium compound selected from the group consisting of aliphatic ammonium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain havingfrom 6 to 20 carbon atoms, at least two alkyl radicals having from 1 to 2 carbon atoms and a radical selected from the group consisting of ethyl, methyl, benzyl, and cyclohexyl, pyridinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain having from 6 to 20 carbon atoms and quinolinium compounds having attached to the nitrogen atom an aliphatic radical containing a hydrocarbon chain havingfrom 6 to 20 carbon atoms, (2) from about 33% to about 77% of a lower alkanoic acid and (3) from about 0% to about 33% of an additive stable in said cationic active aqueous solutionsselected from the group consisting of aluminum salts of lower alkanoic acids, loweralkoxy celluloses, chitoseamine. and polyalkyleneoxide waxes, whereby both the fabric and the soil are imparted with a positive'electrostatic charge and 10 the soil is separated from the fabric by electrostatic re- FOREIGN PATENTS pulsion and dispersed throughout the Washing solution. 443,795 Great Britain Man 1936 Reeeeeeeee Cieee in we file ef the eeeeee 132%; 33322 1131113331111: 123? i? 13?;
UNITED STATES PATENTS 2,129,264 Downing et a1. Sept. 6, 11938 OTHER REFERENCES 2,165,356 Dunbar J ly 1939 Applied Colloid Chemistry (General Theory), 2nd ed. 2,374,213 Katzman Apr. 2 1945 Rev. by Bancroft, pp. 287, 291 (1926), pub. by McGraw 2,459,062 Cook Ian. 11, 1949 10 Hill, N w York, 2,577,773 Lambert 1951 Quaternary Ammonium Germicides, Lawrence, Aca- 2,587,597 Cook et a1 Mar. 4, 1952 demic Press Inc., New York (1950), pp. 185-192.
2,702,179 Funderburk et a1. Feb. (15, 1955
Claims (1)
1. THE METHOD OF CLEANING A SOILED SYNTHETIC TEXTILE FABRIC, WHICH COMPRISES WASHING SAID FABRIC IN A CATIONACTIVE AQUEOUS SOLUTION CONSISTING ESSENTIALLY OF WATER AND FROM ABOUT 0.85 TO ABOUT 1.5 GM./LITER OF A CATIONACTIVE WASHING COMPOSITION COMPRISING (1) FROM ABOUT 23% TO ABOUT 44% OF AN ORGANIC ONIUM COMPOUND SELECTED FROM THE GROUP CONSISTING OF ALIPHATIC AMMONIUM COMPOUNDS HAVING ATTACHED TO THE NITROGEN ATOM AN ALIPHATIC RADICAL CONTAINING A HYDROCARBON CHAIN HAVING FROM 6 TO 20 CARBON ATOMS, AT LEAST TWO ALKYL RADICALS HAVING FROM 1 TO 2 CARBON ATOMS, AND A RADICAL SELECTED FROM THE GROUP CONSISTING OF ETHYL, METHYL, BENZYL AND CYCLOHEXYL, PYRIDINIUM COMPOUNDS HAVING ATTACHED TO THE NITROGEN ATOM AN ALIPHATIC RADICAL CONTAINING A HYDROCARBON CHAIN HAVING FROM 6 TO 20 CARBON ATMS AND QUINOLINIUM COMPOUNDS HAVING ATTACHED TO THE NITROGEN ATOM AN ALIPHATIC RADICAL CONTAINING A HYDROCARBON CHAIN HAVING FROM 6 TO 20 CARBON ATOMS, (2) FROM ABOUT 33% TO ABOUT 77* OF A LOWER ALKANOIC ACID AND (3) ROM ABOUT 0% TO ABOUT 33% OF AN ADDITIVE STABLE IN SAID CATIONIC ACTIVE AQUEOUS SOLUTION SELECTED FROM THE GROUP CONSISTING OF ALUMINUM SALTS OF LOWER ALKANOIC ACIDS, LOWER ALKOY CELLULOSES, CHITOSEAMINE AND POLYALKYLENE OXIDE WAXES, WHEREBY BOTH THE FABRIC AND THE SOIL ARE IMPARTED WITH A POSITIVE ELECTROSTATIC CHARGE AND THE SOIL IS SEPARATED FROM THE FABRIC BY ELECTROSTATIC REPULSION AND DISPERSED THROUGHOUT THE WASHING SOLUTION.
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Cited By (23)
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US3154489A (en) * | 1960-07-18 | 1964-10-27 | Armour & Co | Surface active compositions |
US3174905A (en) * | 1962-03-12 | 1965-03-23 | American Cyanamid Co | Methods and compositions for rendering textile materials soft, germ resistant and antistatic |
US3223643A (en) * | 1964-11-12 | 1965-12-14 | Rohm & Haas | Liquid acid-detergent-sanitizer composition |
US3223644A (en) * | 1964-11-12 | 1965-12-14 | Rohm & Haas | Liquid detergent-sanitizer |
US3347812A (en) * | 1965-06-25 | 1967-10-17 | Marco Carlo G De | Novel water- and oil-resistant fibrous structures, processes and compositions therefor |
US4199464A (en) * | 1977-12-23 | 1980-04-22 | The Procter & Gamble Company | Laundry detergent substrate articles |
US4199465A (en) * | 1977-12-23 | 1980-04-22 | The Procter & Gamble Company | Laundry detergent substrate articles |
US4222905A (en) * | 1978-06-26 | 1980-09-16 | The Procter & Gamble Company | Laundry detergent compositions having enhanced particulate soil removal performance |
US4228042A (en) * | 1978-06-26 | 1980-10-14 | The Procter & Gamble Company | Biodegradable cationic surface-active agents containing ester or amide and polyalkoxy group |
US4228044A (en) * | 1978-06-26 | 1980-10-14 | The Procter & Gamble Company | Laundry detergent compositions having enhanced particulate soil removal and antiredeposition performance |
US4259217A (en) * | 1978-03-07 | 1981-03-31 | The Procter & Gamble Company | Laundry detergent compositions having enhanced greasy and oily soil removal performance |
US4294576A (en) * | 1979-06-23 | 1981-10-13 | Basf Aktiengesellschaft | Removal of oligomer deposits from textile materials |
WO1982002041A1 (en) * | 1980-12-11 | 1982-06-24 | Mason Res Center Virginia | Method for providing long-lasting local anesthesia and compounds and compositions therefore |
US4493773A (en) * | 1982-05-10 | 1985-01-15 | The Procter & Gamble Company | Low phosphate, softening laundry detergent containing ethoxylated nonionic, alkylpolysaccharide and cationic surfactants |
US5614548A (en) * | 1988-10-25 | 1997-03-25 | Wake Forest University | Quaternary amine containing ether or ester lipid derivatives and therapeutic compositions |
US5770584A (en) * | 1993-06-10 | 1998-06-23 | Wake Forest University | Method of treating hepatitis virus infections |
US5962437A (en) * | 1994-08-29 | 1999-10-05 | Wake Forest University | Lipid analogs for treating viral infections |
US20020082242A1 (en) * | 2000-10-19 | 2002-06-27 | Kucera Louis S. | Compositions and methods of double-targeting virus infections and cancer cells |
US20040149809A1 (en) * | 2001-05-29 | 2004-08-05 | Weekamp Johannus Wilhelmus | Metal-ceramic bond |
US20040233811A1 (en) * | 2001-08-31 | 2004-11-25 | Duffield David Jay | Sequence counter for an audio visual stream |
US20040259845A1 (en) * | 1995-08-07 | 2004-12-23 | Wake Forest University | Lipid analogs for treating viral infections |
US20050187191A1 (en) * | 2004-02-20 | 2005-08-25 | Kucera Louis S. | Methods and compositions for the treatment of respiratory syncytial virus |
US7309696B2 (en) | 2000-10-19 | 2007-12-18 | Wake Forest University | Compositions and methods for targeting cancer cells |
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DE2437173C3 (en) * | 1974-06-01 | 1981-10-29 | Heinlein, Karl Hans, Dipl.-Chem. Dr., 6490 Schlüchtern | Method for washing textile material |
GB1473873A (en) * | 1974-06-26 | 1977-05-18 | Ciba Geigy Ag | Photographic silver halide bleach-fix baths |
WO2012022034A1 (en) | 2010-08-18 | 2012-02-23 | Unilever Plc | Improvements relating to fabric treatment compositions comprising targeted benefit agents |
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US3154489A (en) * | 1960-07-18 | 1964-10-27 | Armour & Co | Surface active compositions |
US3174905A (en) * | 1962-03-12 | 1965-03-23 | American Cyanamid Co | Methods and compositions for rendering textile materials soft, germ resistant and antistatic |
US3223643A (en) * | 1964-11-12 | 1965-12-14 | Rohm & Haas | Liquid acid-detergent-sanitizer composition |
US3223644A (en) * | 1964-11-12 | 1965-12-14 | Rohm & Haas | Liquid detergent-sanitizer |
US3347812A (en) * | 1965-06-25 | 1967-10-17 | Marco Carlo G De | Novel water- and oil-resistant fibrous structures, processes and compositions therefor |
US4199464A (en) * | 1977-12-23 | 1980-04-22 | The Procter & Gamble Company | Laundry detergent substrate articles |
US4199465A (en) * | 1977-12-23 | 1980-04-22 | The Procter & Gamble Company | Laundry detergent substrate articles |
US4259217A (en) * | 1978-03-07 | 1981-03-31 | The Procter & Gamble Company | Laundry detergent compositions having enhanced greasy and oily soil removal performance |
US4228042A (en) * | 1978-06-26 | 1980-10-14 | The Procter & Gamble Company | Biodegradable cationic surface-active agents containing ester or amide and polyalkoxy group |
US4228044A (en) * | 1978-06-26 | 1980-10-14 | The Procter & Gamble Company | Laundry detergent compositions having enhanced particulate soil removal and antiredeposition performance |
US4222905A (en) * | 1978-06-26 | 1980-09-16 | The Procter & Gamble Company | Laundry detergent compositions having enhanced particulate soil removal performance |
US4294576A (en) * | 1979-06-23 | 1981-10-13 | Basf Aktiengesellschaft | Removal of oligomer deposits from textile materials |
WO1982002041A1 (en) * | 1980-12-11 | 1982-06-24 | Mason Res Center Virginia | Method for providing long-lasting local anesthesia and compounds and compositions therefore |
US4493773A (en) * | 1982-05-10 | 1985-01-15 | The Procter & Gamble Company | Low phosphate, softening laundry detergent containing ethoxylated nonionic, alkylpolysaccharide and cationic surfactants |
US5614548A (en) * | 1988-10-25 | 1997-03-25 | Wake Forest University | Quaternary amine containing ether or ester lipid derivatives and therapeutic compositions |
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US20020082242A1 (en) * | 2000-10-19 | 2002-06-27 | Kucera Louis S. | Compositions and methods of double-targeting virus infections and cancer cells |
US7309696B2 (en) | 2000-10-19 | 2007-12-18 | Wake Forest University | Compositions and methods for targeting cancer cells |
US20040149809A1 (en) * | 2001-05-29 | 2004-08-05 | Weekamp Johannus Wilhelmus | Metal-ceramic bond |
US20040233811A1 (en) * | 2001-08-31 | 2004-11-25 | Duffield David Jay | Sequence counter for an audio visual stream |
US7551837B2 (en) | 2001-08-31 | 2009-06-23 | Thomson Licensing | Sequence counter for an audio visual stream |
US20050187191A1 (en) * | 2004-02-20 | 2005-08-25 | Kucera Louis S. | Methods and compositions for the treatment of respiratory syncytial virus |
Also Published As
Publication number | Publication date |
---|---|
GB765811A (en) | 1957-01-16 |
FR1105801A (en) | 1955-12-08 |
CH337172A (en) | 1959-03-31 |
GB764007A (en) | 1956-12-19 |
NL189533C (en) | |
DE1050298B (en) | 1959-02-12 |
FR1106094A (en) | 1955-12-12 |
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