US3312623A - Antiseptic detergent compositions - Google Patents
Antiseptic detergent compositions Download PDFInfo
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- US3312623A US3312623A US332882A US33288263A US3312623A US 3312623 A US3312623 A US 3312623A US 332882 A US332882 A US 332882A US 33288263 A US33288263 A US 33288263A US 3312623 A US3312623 A US 3312623A
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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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
Definitions
- bacteriostatic agents are not effective in preventing or arresting the growth or action of micro-organisms such as the Staphylococci, i.e., Staphyloccocus aureus, either by inhibiting their activity or by destroying them.
- bacteriostatic agents must be incorporated into the detergent composition to fulfill this function.
- none of the known bacteriostatic agents which are effective in the presence of detergent compositions aid in the cleansing action and, in fact, some are deleterious to such action.
- a bacteriostatic agent which also exhibits surface active properties and thereby aids the detergent in the cleansing action would represent an advancement in this art.
- dialkyl esters of long-chain alkyl phosphonates having the formula fi/O R1 R1' P wherein R is a member selected from the group consisting of alkyl, hydroxy-alkyl and halo-alkyl containing from about 8 to 18 carbon atoms and preferably from 10 to 14 carbon atoms and R and R are lower alkyl groups (1 to carbons) and preferably containing from 1 to 2 carbon atoms, unexpectedly exhibit bacteriostatic properties as well as surface active properties as will be more fully discussed hereinafter.
- dialkyl esters of long-chain alkyl phosphonates of the present invention can be prepared by many various methods which include reacting a long-chain n-
- Example 1 I Example 2 In the same manner as indicated in Example 1, about 249 parts of trimethylphosphite and about 500 parts of tetradecyl bromide were reacted to yield about 356 parts of dimethyl tetradecyl phosphonate (B.P. 155 C./ .3 mm.).
- Example 3 In the same manner as indicated in Example 1, about 348 parts of triethylphosphite and about 442.4 parts of dodecyl bromide were reacted to yield diethyl dodecyl phosphonate (B.P. 159 C./1.1 mm.).
- detergent includes soap, i.e., an alkali metal or amine salt of a fatty acid and/or fatty acid mixtures, and synthetic detergents, particularly of the anionic, nonionic and amphoteric classes, including mixtures of these.
- antiseptic detergent composition refers to those detergent compositions which are satisfactory detergents and which are effective againts Staphylococcus.
- dialkyl esters of long-chain alkyl phosphonates of the present invention have been found to not only exhibit surface-tension-reducing properties in aqueous systems but also to exhibit effective bacteriostatic properties in such systems in the presence of detergent compositions.
- these bacteriostatic agents neither impart an unpleasant odor nor discolor the finished detergent composition.
- the new antiseptic detergent compositions are not irritating to the skin. It is, of course, a
- bacteriostatic agents of the present invention that they additionally aid the detergent composition in its cleansing action by exhibiting surface active properties in aqueous systems.
- dialkyl esters of long-chain alkyl phosphonates which are suitable for use in detergent compositions can vary depending upon the end use application of the detergent composition, such as soap bars, hair shampoo and the like and, in general, any amount which is antiseptically effective, i.e., effective against Staphylococcus, can be used with amounts below about 50% by weight of the detergent being usually acceptable and amounts from about .05 to 10% being preferred. Under some circumstances, some bacteriostatic activity can be found as low as .001 by weight of the detergent.
- the invention is not to be limited to any particular method of preparing the detergent composition containing the bacteriostatic agent.
- the bacteriostatic agent can be mechanically mixed in, crutched in the detergent in the form of a slurry, or dissolved in a solution of the detergent.
- the bacteriostatic agent can be admixed with the detergent in any of the forms in which the detergent is manufactured in, as well as being added simultaneously or separately to an aqueous solution.
- the bacteriostatic agent is intended to be used amides or amines.
- the resulting antiseptic detergent composition that is, the detergent and the bacteriostatic agent, of the present invention is generally effective when used in aqueous systems in conventional amounts such as is normally used with detergent compositions and which is generally about .2% concentration or below.
- the following table presents the surface tensions in dynes per centimeter of solutions at the indicated concentrations of agents and distilled water at 25 C. as determined by the Du Nuoy principle using the Fisher tensiomat.
- the surface tension of water is about 72.8 dynes/cm. at this temperature.
- a reduction of'the surface tension of water to about 30 dynes in 0.1% solution is considered excellent and if this reduction is maintained practically unchanged to a dilution as low as .001%, the material is considered an extremely active surface-tension-reducing agent.
- the bacteriostatic agents of the present invention are effective in controlling bacterial growth in the presence of detergents such as an Ivory brand neutral high grade toilet soap which is a mixture of alkali metal salts of fatty acids analyzing about 46 weight percent oleic and linoleic acid, about 14 weight percent stearic acid, about 30 weight percent palmitic acid and about weight percent of lower fatty acids (myristic, lauric, etc.), and when incorporated in such a soap in a weight ratio of one part to 50 parts soap are effective in low concentrations (less than about 100 p.p.m.) against an inoculum of a standard culture of Micracoccus pyogenes var.
- detergents such as an Ivory brand neutral high grade toilet soap which is a mixture of alkali metal salts of fatty acids analyzing about 46 weight percent oleic and linoleic acid, about 14 weight percent stearic acid, about 30 weight percent palmitic acid and about weight percent of lower fatty acids (my
- Comparable eifectiveness can 'also be obtained when using other soaps such as Lux brand solid neutral white toilet soap (a mixture of alkali metal salts of fatty acids whose fatty acid content analyzes about 45% oleic and linoleic, about 30% palmitic acid, about 10% stearic acid and about 15% lower fatty acids) as well as anionic, nonionic and amphoteric synthetic detergents.
- Anionic surface active compounds can be broadly described as compounds which contain hydrophilic and. lyophilic groups in their molecular structure and which ionize in an aqueous medium to give anions containing the lyophilic group.
- These compounds are usually the alkali metal salts of organic sulfonates or sulfates, particularly the sodium salts, such as alkyl aryl sulfonates (e.g. sodium dodecyl tbenzene sulfonate), sulfate of straight chain primary alcohols (e.g., sodium lauryl sulfate) and the like.
- alkyl aryl sulfonates e.g. sodium dodecyl tbenzene sulfonate
- sulfate of straight chain primary alcohols e.g., sodium lauryl sulfate
- Nonionic surface active compounds can be broadly described as compounds which do not ionize but acquire hydrophilic characteristics from an oxygenated side chain, usually polyoxyethylene, while the lyophilic part of the molecule may come from fatty acids, phenols, alcohols,
- the polyethylene oxide condensates of alkyl phenols e.g., condensation product formed from 1 mole nonyl phenol and 10 moles ethylene oxide
- the condensation products of aliphatic alcohols and ethylene oxide e.g., condensation product formed from 1 mole tridecanol and 12 moles ethylene oxide
- Amphoteric surface active compounds can be broadly described as compounds which have both anionic and cationic groups in the same molecule. Examples of such compounds include sodium N-methyl taurate and sodium N-coco beta amino propinate.
- a detergent composition of the present invention need contain only a detergent and the diethyl esters of long-chain phosphonates, it will be appreciated that the incorporation in the mixture of additional ingredients commonly used with cleansing agents, such as perfume, builders (e.g. sodium tripolyphosphate), anti-redeposition agents (e.g., carboxymethylcellulose), brightening agents (e.g., fluorescent dyes) and the like, is contemplated as being within the invention.
- cleansing agents such as perfume, builders (e.g. sodium tripolyphosphate), anti-redeposition agents (e.g., carboxymethylcellulose), brightening agents (e.g., fluorescent dyes) and the like, is contemplated as being within the invention.
- Example 4 A detergent composition is formulated as follows:
- the above composition is prepared by melting the soap in 'a suitable vessel at about 60 to 70 C. and adding the phosphonate to the soap with agitation. The admixture is then'tpoured into a suitable mold and allowed to solidify by cooling to room temperature (about 25 C.).
- Example 5 A liquid detergent emulsion com-position is formulated as follows:
- Nonionic organic active nonyl phenol-ethylene oxide condensate
- Maleic anhydride-ethylene copolymer 1.0 Tetrapotassi um pyrophosphate 20.0 Potassium hydroxide (45% by weight) 6.7 Sodium silicate (Na O:SiO of 1:2) (44.0% by weight) 10.0 Diethyl dodecyl phosphonate 1.0
- the above composition is prepared by heating the water to about 60 C. :and thereafter adding the above additives to the water in a mixer in their above listed order,
- each additive being added and mixed under high shear agitation over a period of about 1 to about 7 minutes while ensuring that the temperature of the mix does not exceed about C.
- Example 6 An antiseptic shampoo composition is formulated as follows:
- R is a member selected from the group consisting of alkyl and halo-alkyl containing from about 8 to 18 carbon atoms and R and R are lower alkyl groups containing from 1 to 5 carbon atoms.
- R contains from 10 to 14 carbon atoms and R and R contain from 1 to 2 carbon atoms.
- dialkyl ester of a long chain alkyl phosphonate is diethyl dodecyl phosphonate.
Description
United States Patent 3,312,623 ANTISEPTIC DETERGENT COMPOSITIONS Steven J. Fitch, Creve Coeur, and Riyad R. Irani, Olivette, Mo., assignors to Monsanto Company, a corporation of Delaware No Drawing. Filed Dec. 23, 1963, Ser. No. 332,882 7 Claims. (Cl. 252-106) This invention relates to new and novel detergent compositions and more particularly to detergent compositions containing a bacteriostatic agent.
Detergents of themselves are not effective in preventing or arresting the growth or action of micro-organisms such as the Staphylococci, i.e., Staphyloccocus aureus, either by inhibiting their activity or by destroying them. Thus, when such action is desired bacteriostatic agents must be incorporated into the detergent composition to fulfill this function. However, none of the known bacteriostatic agents which are effective in the presence of detergent compositions aid in the cleansing action and, in fact, some are deleterious to such action. As can be appreciated, therefore, a bacteriostatic agent which also exhibits surface active properties and thereby aids the detergent in the cleansing action would represent an advancement in this art.
It is, therefore, an object of this invention to provide improved antiseptic detergent compositions.
It is a further object of this invention to provide detergent compositions having incorporated therein a bacteriostatic agent which exhibits surface active properties.
Other objects will become apparent from a reading of the following detailed description and the claims appended hereto.
It has been found that dialkyl esters of long-chain alkyl phosphonates having the formula fi/O R1 R1' P wherein R is a member selected from the group consisting of alkyl, hydroxy-alkyl and halo-alkyl containing from about 8 to 18 carbon atoms and preferably from 10 to 14 carbon atoms and R and R are lower alkyl groups (1 to carbons) and preferably containing from 1 to 2 carbon atoms, unexpectedly exhibit bacteriostatic properties as well as surface active properties as will be more fully discussed hereinafter.
Compounds of the present invention which are suitable for use according to the teachings contained herein inelude:
(l) dimethyl octylphosphonate (2) dibutyl dodecylphosphonate (3) dipropyl decylphosphonate (4) diethyl dodecylphosphonate (5) dimethyl octadecyl-phosphonate (6) diethyl hexadecylphosphonate (7) dipropyl tetradecylphosphonate (8) dibutyl tetradecylphosphonate (9) dimethyl decylphosphonate (10) diethyl decylphosphonate (ll) diethyl l-hydroxydodecylphosphonate (12) diethyl l-hydroxydecylphosphonate (13) dimethyl l-chlorododecylphosphonate (l4) diethyl 3-bromodecylphosphonate The dialkyl esters of long-chain alkyl phosphonates of the present invention can be prepared by many various methods which include reacting a long-chain n-alkyl halide (chloride or bromide) with a tri-lower alkyl phosphite under conditions of elevated temperatures, i.e, about 120-170 C., for a period of a few hours. The following is the reaction in equation form:
The following examples are presented to illustrate the invention, with parts by weight being used in the examples unless otherwise indicated.
Example 1 I Example 2 In the same manner as indicated in Example 1, about 249 parts of trimethylphosphite and about 500 parts of tetradecyl bromide were reacted to yield about 356 parts of dimethyl tetradecyl phosphonate (B.P. 155 C./ .3 mm.).
Example 3 In the same manner as indicated in Example 1, about 348 parts of triethylphosphite and about 442.4 parts of dodecyl bromide were reacted to yield diethyl dodecyl phosphonate (B.P. 159 C./1.1 mm.).
The term detergent includes soap, i.e., an alkali metal or amine salt of a fatty acid and/or fatty acid mixtures, and synthetic detergents, particularly of the anionic, nonionic and amphoteric classes, including mixtures of these. The term antiseptic detergent composition refers to those detergent compositions which are satisfactory detergents and which are effective againts Staphylococcus.
The dialkyl esters of long-chain alkyl phosphonates of the present invention have been found to not only exhibit surface-tension-reducing properties in aqueous systems but also to exhibit effective bacteriostatic properties in such systems in the presence of detergent compositions. In addition, these bacteriostatic agents neither impart an unpleasant odor nor discolor the finished detergent composition. Furthermore, the new antiseptic detergent compositions are not irritating to the skin. It is, of course, a
distinct advantage of the bacteriostatic agents of the present invention that they additionally aid the detergent composition in its cleansing action by exhibiting surface active properties in aqueous systems.
The amounts of the dialkyl esters of long-chain alkyl phosphonates which are suitable for use in detergent compositions can vary depending upon the end use application of the detergent composition, such as soap bars, hair shampoo and the like and, in general, any amount which is antiseptically effective, i.e., effective against Staphylococcus, can be used with amounts below about 50% by weight of the detergent being usually acceptable and amounts from about .05 to 10% being preferred. Under some circumstances, some bacteriostatic activity can be found as low as .001 by weight of the detergent.
The invention is not to be limited to any particular method of preparing the detergent composition containing the bacteriostatic agent. The bacteriostatic agent can be mechanically mixed in, crutched in the detergent in the form of a slurry, or dissolved in a solution of the detergent. In addition, the bacteriostatic agent can be admixed with the detergent in any of the forms in which the detergent is manufactured in, as well as being added simultaneously or separately to an aqueous solution. In any event, the bacteriostatic agent is intended to be used amides or amines.
3 with the detergent at the time of application as a cleansing agent.
The resulting antiseptic detergent composition, that is, the detergent and the bacteriostatic agent, of the present invention is generally effective when used in aqueous systems in conventional amounts such as is normally used with detergent compositions and which is generally about .2% concentration or below.
In order to illustrate the surface active properties of the bacteriostatic agent of the instant invention, the following table presents the surface tensions in dynes per centimeter of solutions at the indicated concentrations of agents and distilled water at 25 C. as determined by the Du Nuoy principle using the Fisher tensiomat. The surface tension of water is about 72.8 dynes/cm. at this temperature. A reduction of'the surface tension of water to about 30 dynes in 0.1% solution is considered excellent and if this reduction is maintained practically unchanged to a dilution as low as .001%, the material is considered an extremely active surface-tension-reducing agent.
As previously mentioned, the bacteriostatic agents of the present invention are effective in controlling bacterial growth in the presence of detergents such as an Ivory brand neutral high grade toilet soap which is a mixture of alkali metal salts of fatty acids analyzing about 46 weight percent oleic and linoleic acid, about 14 weight percent stearic acid, about 30 weight percent palmitic acid and about weight percent of lower fatty acids (myristic, lauric, etc.), and when incorporated in such a soap in a weight ratio of one part to 50 parts soap are effective in low concentrations (less than about 100 p.p.m.) against an inoculum of a standard culture of Micracoccus pyogenes var. aureus (Staphylococcus aureus) of standard resistance in 'a Sabourards dextrose agar medium. Diethyl dodecyl phosphonate appears to exhibit the greatest effectiveness, i.e., effective at concentrations as low as about 1 to 20 p.p.m., and is therefore preferred.
Comparable eifectiveness can 'also be obtained when using other soaps such as Lux brand solid neutral white toilet soap (a mixture of alkali metal salts of fatty acids whose fatty acid content analyzes about 45% oleic and linoleic, about 30% palmitic acid, about 10% stearic acid and about 15% lower fatty acids) as well as anionic, nonionic and amphoteric synthetic detergents. Anionic surface active compounds can be broadly described as compounds which contain hydrophilic and. lyophilic groups in their molecular structure and which ionize in an aqueous medium to give anions containing the lyophilic group. These compounds are usually the alkali metal salts of organic sulfonates or sulfates, particularly the sodium salts, such as alkyl aryl sulfonates (e.g. sodium dodecyl tbenzene sulfonate), sulfate of straight chain primary alcohols (e.g., sodium lauryl sulfate) and the like. Nonionic surface active compounds can be broadly described as compounds which do not ionize but acquire hydrophilic characteristics from an oxygenated side chain, usually polyoxyethylene, while the lyophilic part of the molecule may come from fatty acids, phenols, alcohols,
For example purposes only, the polyethylene oxide condensates of alkyl phenols (e.g., condensation product formed from 1 mole nonyl phenol and 10 moles ethylene oxide), the condensation products of aliphatic alcohols and ethylene oxide (e.g., condensation product formed from 1 mole tridecanol and 12 moles ethylene oxide) are suitable nonionic surface active compounds in practicing the invention. Amphoteric surface active compounds can be broadly described as compounds which have both anionic and cationic groups in the same molecule. Examples of such compounds include sodium N-methyl taurate and sodium N-coco beta amino propinate.
While a detergent composition of the present invention need contain only a detergent and the diethyl esters of long-chain phosphonates, it will be appreciated that the incorporation in the mixture of additional ingredients commonly used with cleansing agents, such as perfume, builders (e.g. sodium tripolyphosphate), anti-redeposition agents (e.g., carboxymethylcellulose), brightening agents (e.g., fluorescent dyes) and the like, is contemplated as being within the invention.
A further understanding of the detergent compositions described herein and processes for preparing the compositions will be obtained from the following specific examples which are intended to illustrate this invention, but
- not to limit the scope thereof, parts and percentages being by weight unless otherwise indicated.
Example 4 A detergent composition is formulated as follows:
The above composition is prepared by melting the soap in 'a suitable vessel at about 60 to 70 C. and adding the phosphonate to the soap with agitation. The admixture is then'tpoured into a suitable mold and allowed to solidify by cooling to room temperature (about 25 C.).
Example 5 A liquid detergent emulsion com-position is formulated as follows:
Additive: Parts Water 46.1 Sodium carboxymethylcellulose (95% by weight) .5 Fluorescent dye .025 Dis-odium acid pyrophosphate 5.0
Nonionic organic active (nonyl phenol-ethylene oxide condensate) 10.0 Maleic anhydride-ethylene copolymer 1.0 Tetrapotassi um pyrophosphate 20.0 Potassium hydroxide (45% by weight) 6.7 Sodium silicate (Na O:SiO of 1:2) (44.0% by weight) 10.0 Diethyl dodecyl phosphonate 1.0
The above composition is prepared by heating the water to about 60 C. :and thereafter adding the above additives to the water in a mixer in their above listed order,
each additive being added and mixed under high shear agitation over a period of about 1 to about 7 minutes while ensuring that the temperature of the mix does not exceed about C.
Example 6 An antiseptic shampoo composition is formulated as follows:
Additive: Parts Triethanol lauryl sulfate 60 Methyl cellulose 2 Parts Propylene glycol 4 Potassium stearate 6 Water 130 Diethyldodecyl phosphonate 2 The above composition is prepared by melting the potassium stearate at about 60 to 70 C. and adding thereto the triethanol lauryl sulfate, methyl cellulose,
propylene glycol and diethyl dodecyl phosphonate until wherein R is a member selected from the group consisting of alkyl and halo-alkyl containing from about 8 to 18 carbon atoms and R and R are lower alkyl groups containing from 1 to 5 carbon atoms.
2. The antiseptic detergent composition of claim 1,
wherein R contains from 10 to 14 carbon atoms and R and R contain from 1 to 2 carbon atoms.
3. The antiseptic detergent composition of claim 2, wherein said dialkyl ester of a long chain phosphonate is present in amounts below about by weight of said composition. 7
4. The antiseptic detergent composition of claim 3, wherein said detergent is soap.
5. The antiseptic detergent composition of claim 3, wherein said detergent is a synthetic detergent selected from the class consisting of non-soap anionic, nonionic and amphoteric surfactants.
6. The antiseptic detergent composition of claim 2, wherein said dialkyl ester of a long chain alkyl phosphonate is diethyl dodecyl phosphonate.
7. The antiseptic detergent composition of claim 6, wherein said diethyl dodecyl phosphonate is present in amounts from about .05% to 10% by weight of said detergent composition.
References Cited by the Examiner UNITED STATES PATENTS 2,251,934 8/1941 Hartung 252-107 2,43 6,141 2/ 1948 Goebel 260-461 2,579,810 12/1951 Gields 167-22 2,681,920 6/1954 Van Winkle et :al. 167-22 2,904,468 9/1959 Davis et a1 252-106 X 3,118,842 1/1964 Besser 252-106 LEON D. ROSDOL, Primary Examiner.
JULIUS GREENWALD, W. SCHULZ,
Assistant Examiners.
Claims (1)
1. AN ANTISEPTIC DETERGENT COMPOSITION CONSISTING ESSENTIALLY OF A DETERGENT SELECTED FROM THE CLASS CONSISTING OF SOAP AND ORGANIC SYNTHETIC DETERGENT SELECTED FROM THE CLASS CONSISTING OF NON-SOAP ANIONIC, NONIONIC AND A AMPHOTERIC SURFACTANTS AND, AS A BACTERIOSTATIC AGENT, IN AT LEAST AN ANTISEPTICALLY EFFECTIVE AMOUNT, A DIALKYL ESTER OF A LONG CHAIN ALKYL PHOSPHATE HAVING THE FOLLOWING FORMULA
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US332882A US3312623A (en) | 1963-12-23 | 1963-12-23 | Antiseptic detergent compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US332882A US3312623A (en) | 1963-12-23 | 1963-12-23 | Antiseptic detergent compositions |
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| US3312623A true US3312623A (en) | 1967-04-04 |
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Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3764676A (en) * | 1970-10-28 | 1973-10-09 | Gates Rubber Co | Diethyl cyanomethyl phosphonate as an antimicrobial agent |
| US3764677A (en) * | 1971-06-25 | 1973-10-09 | Gates Rubber Co | Diethyl betaaminoethylphosphonate as an antimicrobial agent |
| US3783160A (en) * | 1970-10-28 | 1974-01-01 | Gates Rubber Co | Diethyl allyl phosphonate as an anti-microbial agent |
| US4235733A (en) * | 1978-07-13 | 1980-11-25 | Kao Soap Co., Ltd. | Antibacterial soap containing trichlorohydroxy diphenyl ether bactericide and an organic phosphoric ester as a stabilizer therefor |
| US4273768A (en) * | 1980-05-19 | 1981-06-16 | The United States Of America As Represented By The Secretary Of Agriculture | Control of nematodes and other helminths |
| DE3240688A1 (en) * | 1982-11-04 | 1984-05-30 | Henkel KGaA, 4000 Düsseldorf | USE OF ALKYLMONOPHOSPHONIC ACIDS AS A KILLING SUBSTANCE |
| US4753749A (en) * | 1984-03-08 | 1988-06-28 | Interface Research Corporation | Microbiocidal cleaning agent and preparation thereof |
| US4908209A (en) * | 1983-08-16 | 1990-03-13 | Interface, Inc. | Biocidal delivery system of phosphate ester and method of preparation thereof |
| US4935232A (en) * | 1983-08-16 | 1990-06-19 | Interface Research Corporation | Microbiocidal composition and method of preparation thereof |
| US4957948A (en) * | 1988-05-05 | 1990-09-18 | Interface, Inc. | Biocidal protective coating for heat exchanger coils |
| US5024840A (en) * | 1984-03-08 | 1991-06-18 | Interface, Inc. | Antimicrobial carpet and carpet tile |
| US5032310A (en) * | 1983-08-16 | 1991-07-16 | Interface, Inc. | Microbiocidal cleansing and disinfecting formulations and preparation thereof |
| US5133933A (en) * | 1983-08-16 | 1992-07-28 | Interface Research Corporation | Microbiocidal preservative |
| US5474739A (en) * | 1978-02-04 | 1995-12-12 | Interface, Inc. | Microbiocidal composition |
| US5635192A (en) * | 1988-05-05 | 1997-06-03 | Interface, Inc. | Biocidal polymeric coating for heat exchanger coils |
| US5682593A (en) * | 1994-10-26 | 1997-10-28 | Bayer Aktiengesellschaft | Extraction of acids and metal salts from aqueous solutions with diethyl dodecylphosphonate |
| US20080108537A1 (en) * | 2006-11-03 | 2008-05-08 | Rees Wayne M | Corrosion inhibitor system for mildly acidic to ph neutral halogen bleach-containing cleaning compositions |
| US7537789B1 (en) * | 2005-07-15 | 2009-05-26 | Envirovest Llc | System controlling soluble phosphorus and nitrates and other nutrients, and a method of using the system |
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| US2579810A (en) * | 1949-08-18 | 1951-12-25 | Research Corp | Process of preparing substituted hydroxymethylphosphonic esters |
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| US2251934A (en) * | 1936-09-21 | 1941-08-12 | Sharp & Dohme Inc | Germicidal soap |
| US2436141A (en) * | 1946-03-07 | 1948-02-17 | Du Pont | Dialkyl esters of long-chain alkylphosphonates |
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| US2681920A (en) * | 1951-01-16 | 1954-06-22 | Shell Dev | Preparation of phosphonates |
| US2904468A (en) * | 1954-04-13 | 1959-09-15 | Carlen Corp | Skin disinfectant containing polyoxyethylene alkyl phenol, calcium chelating agent and either an organic sulfate or sulfonate salt |
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Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3783160A (en) * | 1970-10-28 | 1974-01-01 | Gates Rubber Co | Diethyl allyl phosphonate as an anti-microbial agent |
| US3764676A (en) * | 1970-10-28 | 1973-10-09 | Gates Rubber Co | Diethyl cyanomethyl phosphonate as an antimicrobial agent |
| US3764677A (en) * | 1971-06-25 | 1973-10-09 | Gates Rubber Co | Diethyl betaaminoethylphosphonate as an antimicrobial agent |
| US5474739A (en) * | 1978-02-04 | 1995-12-12 | Interface, Inc. | Microbiocidal composition |
| US4235733A (en) * | 1978-07-13 | 1980-11-25 | Kao Soap Co., Ltd. | Antibacterial soap containing trichlorohydroxy diphenyl ether bactericide and an organic phosphoric ester as a stabilizer therefor |
| US4273768A (en) * | 1980-05-19 | 1981-06-16 | The United States Of America As Represented By The Secretary Of Agriculture | Control of nematodes and other helminths |
| US4528110A (en) * | 1982-11-04 | 1985-07-09 | Henkel Kommanditgesellschaft Auf Aktien | Method of using alkyl monophosphoric acids as germicidal agents |
| DE3240688A1 (en) * | 1982-11-04 | 1984-05-30 | Henkel KGaA, 4000 Düsseldorf | USE OF ALKYLMONOPHOSPHONIC ACIDS AS A KILLING SUBSTANCE |
| US4908209A (en) * | 1983-08-16 | 1990-03-13 | Interface, Inc. | Biocidal delivery system of phosphate ester and method of preparation thereof |
| US4935232A (en) * | 1983-08-16 | 1990-06-19 | Interface Research Corporation | Microbiocidal composition and method of preparation thereof |
| US5032310A (en) * | 1983-08-16 | 1991-07-16 | Interface, Inc. | Microbiocidal cleansing and disinfecting formulations and preparation thereof |
| US5133933A (en) * | 1983-08-16 | 1992-07-28 | Interface Research Corporation | Microbiocidal preservative |
| US4753749A (en) * | 1984-03-08 | 1988-06-28 | Interface Research Corporation | Microbiocidal cleaning agent and preparation thereof |
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| US4957948A (en) * | 1988-05-05 | 1990-09-18 | Interface, Inc. | Biocidal protective coating for heat exchanger coils |
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