| PATENT NUMBER | This data is not available for free |
| PATENT GRANT DATE | November 13, 2001 |
| PATENT TITLE |
Urethane surfactants and their use in personal care formulations |
| PATENT ABSTRACT | The present invention is directed to monomeric and polymeric compositions based upon polymeric urethane surfactants which are derived from linear, branched, or aromatic compounds of synthetic or natural origin, preferably from tertiary amines and diisocyanate compounds. The urethane polymers of the present invention may be in the form of betaines, quaternium salts, tertiary amine salts or N-oxides. The compounds of the present invention may be incorporated into personal care formulations such as cosmetics, dental care products and toiletries to improve at least one and preferably two or more characteristics of such formulations |
| PATENT INVENTORS | This data is not available for free |
| PATENT ASSIGNEE | This data is not available for free |
| PATENT FILE DATE | March 24, 1999 |
| PATENT CLAIMS |
What is claimed is: 1. A compound according to the structure: ##STR15## where R' is a C.sub.6 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric, a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; R" is selected from a C.sub.1 through C.sub.36 linear, branch-chained or cyclic saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric, a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl, substituted alkylphenyl or alkylbenzyl group, ##STR16## R'" is selected from a C.sub.1 through C.sub.36 linear or branch-chained, cyclic, saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric or a phenyl group, benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl, substituted alkylphenyl or alkylbenzyl group; and R.sub.1 is selected from a C.sub.1 through C.sub.36 linear or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group, including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; R.sub.2 is a free electron pair, O, a hydrogen or a quaternium group, or a mixture of hydrogen and quaternium groups, with the proviso that when R.sub.2 is H and/or a quaternium group, the nitrogen to which said hydrogen or quaternium group is bonded is positively charged and forms a salt with a negatively charged counterion T; R.sub.3 is a C.sub.1 through C.sub.36 linear or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; each of X and Y is independently a C.sub.1 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, a phenyl or benzyl group or a substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; W is H; and n is an integer from 1 to 1000. 2. The compound according to claim 1 wherein R' is an isophorone group. 3. The compound according to claim 1 where R.sub.2 is a quaternium group and R.sub.3 is a C.sub.2 to C.sub.22 hydrocarbon group. 4. The compound according to claim 3 wherein R' is an isophorone group. 5. The compound according to claim 1 wherein R.sub.2 is a quaternium group. 6. The compound according to claim 1 wherein R.sub.3 is a C.sub.2 to C.sub.22 hydrocarbon group. 7. A method of enhancing or modifying at least one of the characteristics of a personal care product selected from the group consisting of skin and hair adherence, viscosity, substantivity, conditioning, irritation and wetting comprising adding to said personal care product an effective amount of at least one compound according to the structure: ##STR17## where R' is a C.sub.6 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric, a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; R" is selected from a C.sub.1 through C.sub.36 linear, branch-chained or cyclic saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric, a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl, substituted alkylphenyl or alkylbenzyl group, ##STR18## R'" is selected from a C.sub.1 through C.sub.36 linear or branch-chained, cyclic, saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric or a phenyl group, benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl, substituted alkylphenyl or alkylbenzyl group; and R.sub.1 is selected from a C.sub.1 through C.sub.36 linear or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group, including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; R.sub.2 is a free electron pair, O, a hydrogen or a quaternium group, or a mixture of hydrogen and quaternium groups, with the proviso that when R.sub.2 is H and/or a quaternium group, the nitrogen to which said hydrogen or quaternium group is bonded is positively charged and forms a salt with a negatively charged counterion T; R.sub.3 is a C.sub.1 through C.sub.36 linear or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; each of X and Y is independently a C.sub.1 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, a phenyl or benzyl group or a substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; W is H; and n is an integer from 1 to 1000. 8. A method of enhancing or modifying at least one of the characteristics of a personal care product selected from the group consisting of skin and hair adherence, viscosity, substantivity, conditioning, irritation and wetting comprising adding to said personal care product an effective amount of at least one compound according to the structure: ##STR19## where R' is a C.sub.6 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric, a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; R" is selected from a C.sub.1 through C.sub.36 linear, branch-chained or cyclic saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric, a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl, substituted alkylphenyl or alkylbenzyl group, ##STR20## R'" is selected from a C.sub.1 through C.sub.36 linear or branch-chained, cyclic, saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric or a phenyl group, benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl, substituted alkylphenyl or alkylbenzyl group; and R.sub.1 is selected from a C.sub.1 through C.sub.36 linear or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group, including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; R.sub.2 is a free electron pair, O, a hydrogen or a quaternium group, or a mixture of hydrogen and quaternium groups, with the proviso that when R.sub.2 is H and/or a quaternium group, the nitrogen to which said hydrogen or quaternium group is bonded is positively charged and forms a salt with a negatively charged counterion T; R.sub.3 is a C.sub.1 through C.sub.36 linear or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; each of X and Y is independently a C.sub.1 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, a phenyl or benzyl group or a substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; W is H, a sulfosuccinate group or a C.sub.4 -C.sub.10 alkyl sulfonate group, a phosphate group ##STR21## group where V is a C.sub.1 through C.sub.10 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group and R.sub.5 is a C.sub.1 to C.sub.6 alkyl group or a metal cation selected from the group consisting of Na+, K+, Ca++ and Mg++; and n is an integer from 1 to 1000. 9. The method according to claim 7 where R.sub.2 is a quaternium group, R.sub.3 is a C.sub.2 to C.sub.22 hydrocarbon group and W is H. 10. The method according to claim 7 wherein R.sub.2 is a quaternium group. 11. The method according to claim 7 wherein R.sub.3 is a C.sub.2 to C.sub.22 hydrocarbon group. 12. The method according to claim 7 wherein n is 2 to 150. 13. The method according to claim 8 wherein n is 2 to 150. 14. A personal care product composition to be used in contact with the skin, hair or nails said personal care product comprising a mixture of effective amounts of components selected from the group consisting of water, solvents, emollients, humectants, emulsifiers, surfactants, thickeners, coloring agents, preservatives and fragrances, said composition further comprising an effective amount of at least one compound according to the structure: ##STR22## where R' is a C.sub.6 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric, a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; R" is selected from a C.sub.1 through C.sub.36 linear, branch-chained or cyclic saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric, a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl, substituted alkylphenyl or alkylbenzyl group, ##STR23## R'" is selected from a C.sub.1 through C.sub.36 linear or branch-chained, cyclic, saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric or a phenyl group, benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl, substituted alkylphenyl or alkylbenzyl group; and R.sub.1 is selected from a C.sub.1 through C.sub.36 linear or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group, including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; R.sub.2 is a free electron pair, O, a hydrogen or a quaternium group, or a mixture of hydrogen and quaternium groups, with the proviso that when R.sub.2 is H and/or a quaternium group, the nitrogen to which said hydrogen or quaternium group is bonded is positively charged and forms a salt with a negatively charged counterion T; R.sub.3 is a C.sub.1 through C.sub.36 linear or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; each of X and Y is independently a C.sub.1 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, a phenyl or benzyl group or a substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; W is H; and n is an integer from 1 to 1000. 15. The compound according to claim 3 wherein R' is a C.sub.6 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group; R" is a C.sub.1 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group; R'" is a C.sub.1 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group; R.sub.1 is a C.sub.2 through C.sub.22 linear or branch-chained saturated or unsaturated unsubstituted hydrocarbon group; R.sub.2 is a hydrogen or a quaternium group; R.sub.3 is a C.sub.2 through C.sub.22 linear or branch-chained saturated or unsaturated unsubstituted hydrocarbon group; and n is an integer from 2 to 150. 16. The method according to claim 8 wherein R' is a C.sub.6 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group; R" is a C.sub.1 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group; R'" is a C.sub.1 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group; R.sub.1 is a C.sub.2 through C.sub.22 linear or branch-chained saturated or unsaturated unsubstituted hydrocarbon group; R.sub.2 is a hydrogen or a quaternium group; R.sub.3 is a C.sub.2 through C.sub.22 linear or branch-chained saturated or unsaturated unsubstituted hydrocarbon group; and n is an integer from 2 to 150. 17. The method according to claim 8 wherein R' is an isophorone group. 18. The composition according to claim 14 wherein R' is a C.sub.6 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group; R" is a C.sub.1 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group; R'" is a C.sub.1 through C.sub.36 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group; R.sub.1 is a C.sub.2 through C.sub.22 linear or branch-chained saturated or unsaturated unsubstituted hydrocarbon group; R.sub.2 is a hydrogen or a quaternium group; R.sub.3 is a C.sub.2 through C.sub.22 linear or branch-chained saturated or unsaturated unsubstituted hydrocarbon group; and n is an integer from 2 to 150. 19. The composition according to claim 14 wherein R.sub.2 is a quaternium group and R.sub.3 is a C.sub.2 to C.sub.22 hydrocarbon group. 20. The composition according to claim 14 wherein R.sub.2 is a quaternium group. 21. The composition according to claim 14 wherein R.sub.3 is a C.sub.2 to C.sub.22 hydrocarbon group. 22. The composition according to claim 14 wherein n is 2 to 150. 23. The composition according to claim 14 wherein R' is an isophorone group. 24. The method according to claim 8 wherein the inclusion of said compound enhances or modifies at least two characteristics of said personal care product. 25. The method according to claim 7 wherein R' is an isophorone group. 26. The method according to claim 8 wherein R' is an isophorone group. 27. The composition according to claim 14 wherein R' is an isophorone group. 28. The compound according to claim 1 wherein R' is an isophorone group. -------------------------------------------------------------------------------- |
| PATENT DESCRIPTION |
FIELD OF THE INVENTION The present invention is directed to monomeric and polymeric compositions based upon urethane surfactants which are generally derived from linear, branched, or aromatic compounds of synthetic or natural origin, preferably from tertiary amines and diisocyanate compounds. The urethane betaines of the present invention may be incorporated into personal care formulations such as cosmetics, dental care products and toiletries to improve or modify at least two of the characteristics of such formulations. BACKGROUND OF THE INVENTION Surfactants, such as Betaines, amine oxides and quaternaries (from C.sub.6 -C.sub.22) have been used on a commercial basis in the cosmetic, toiletry and personal care industry for the past 40 years primarily as surfactants for their mildness and lack of irritation on a commercial basis. The aforementioned surfactants have been prepared from natural oils, such as coconut oil, palm kernal oil, soybean oil, safflower seed oil, corn oil, etc. The oils are reacted with amine derivatives such as dimethylaminopropylamine, diethylaminopropyl amine, etc. via transamidation with caustic catalysts to yield the linear C.sub.6 through C.sub.22 dimethylaminopropyl amine derivatives. Similarly, linear fatty acids ranging from C.sub.6 through C.sub.22 have been reacted to form the linear tertiary amine salts which upon application of heat drove off water to form the corresponding C.sub.6 through C.sub.22 linear dimethylaminopropylamine derivative. Aromatic acids such as benzoic acid as well as branched acids similarly have been reacted to form the resultant aromatic dimethylamidopropyl amine or iso-dimethylamido propylamine which could serve as a building block for the betaine. However, aromatic backboned surfactants have not found wide commercial use. Over the years, betaines, amine oxides and quaternaries have become commodity products used in a wide array of applications ranging from shampoos, nonirritating baby shampoos, liquid soaps, dish detergents (to preclude introduction of phosphate builders), body scrubs, shaving creams, etc. When the pH of a cosmetic or toiletry product incorporating betaines is dropped to a pH slightly below about 7.0, the betaine becomes mildly cationic and improved feel and combability of hair results. When coupled with amine oxides, the combination yields a high degree of hair detangling characteristics in shampoos. The inclusion of betaines and amine oxides into liquid soaps in combination with alpha olefin sulfonates and amides ranging in size from C.sub.12 -C.sub.18 at a pH under 7.0, effectively functions as a thickening agent in a liquid soap which leaves the hands soft and silky. Betaines with a preponderance of C.sub.12 through C.sub.14 groups have been shown to be effective foaming agents when used in combination with sodium lauryl sulfate, sodium lauryl ether sulfates and alpha olefin sulfonates. Betaines as well as amine oxides with chain lengths ranging from C.sub.16 through C.sub.22 exhibit special effectiveness as thickening and conditioning agents. The introduction of a betaine of dimethyl oleyl betaine into a shampoo or body lotion does little to promote foam; however, viscosity of a resultant formulation with up to 2.0 percent of higher molecular weight chains such as oleyl, erucyl, arachidyl give significant thickening. Betaines, amine oxides and quaternaries have been found to be extremely effective as tartar-removing agents in toothpaste formulations. A great deal of work had been done in this research arena in the early '70s. When betaines were introduced into toothpaste formulations, teeth were found to be "squeaky clean". However, a major drawback in using these compositions was the taste which was very difficult to mask with flavors. Consequently, as a result of this foul taste, no major brands of toothpaste were introduced to the marketplace. Numerous betaine derivatives were made but were never commercialized. Betaines have also demonstrated properties of corrosion inhibition and have been incorporated into industrial formulations. The lower molecular weight betaines ranging from C.sub.6 through C.sub.18 have found wide use in industrial applications. Another area in which betaines and amine oxides have been used in large volume with considerable success is in the oil and oil-field-related industry. As surfactants in the oil industry, betaines and amine oxides are used as emulsifiers, wetting agents, antifoulants, cleaners and detergents. With respect to paraffinic chemicals, betaines are used as surfactants for breaking up emulsions and as defoamers, for cleaning tanks, dispersing paraffins and as wetting agents for paraffinies. Betaines are also used in aqueous-isopropanol solutions to improve water injectivity in water flooding, as corrosion preventatives in floods, as a surfactant for clarification in water containing H.sub.2 S, to assist in the control of fouling due to microbial action, to enhance scale inhibition and also as an emulsifier and coupler in oil well formulations. With the fairly recent concern with nitrosoamines which may be present as minor contaminants in widely used diethanolamide amines (derived from fatty acids as well as methyl esters), betaines and amine oxides have become used in extremely large quantities in consumer products such as shampoos, body baths, liquid soaps, etc. OBJECTS OF THE INVENTION It is an object of the present invention to provide novel betaine, amine oxide and quaternary compositions which can be used to improve or modify the characteristics of personal care products. Methods for improving or modifying the personal care products are another object of the present invention. Secondary objects of the invention, depending upon the specific embodiment, may include one or more of the following: A. To provide urethane polymers for use as conditioners, antistats, detanglers, facilitators for ease of wet/dry combing, to assist in the minimization of split ends (in hair products), as emulsifiers and for the maximization of color in colored hair products (dyes). B. To introduce into hair and skin contacting formulations polymeric urethane surfactants that will maintain stability and become mildly cationic when used at a pH of less than about 7.0. C. To increase the "adhesion" of the entire molecule to the hair and skin through the structure of the urethane linkages. D. To provide a basis for "thickening" or increasing viscosity in given hair and skin contacting formulations as a result of the polymeric urethane structure of the surfactant molecule used. E. To provide polymeric urethane surfactants for use as a cosmetic raw material in skin and hair contacting formulations to yield mildness and at the same time have low LD.sub.50 values. F. To introduce novel and unique polymeric betaines, amine oxides and quaternaries that are derived from, but not necessarily limited to, renewable vegetable sources making it possible to avoid bovine derived raw materials. These and other objects of the present invention may be readily gleaned from the description of the invention which follows. SUMMARY OF THE INVENTION The present invention relates to polymeric urethane compounds, preferably derived from components obtained from naturally occurring sources. The present invention relates to compounds of the formula: ##STR1## where R' is a C.sub.2 through C.sub.36 (preferably, C.sub.6 through C.sub.22) linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric, an aromatic group, including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; R" is selected from a C.sub.1 through C.sub.36 (preferably, C.sub.6 through C.sub.22) linear, branch-chained or cyclic saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric, a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl, substituted alkylphenyl or alkylbenzyl group, an alkylene oxide group (R.sub.4 --O).sub.m where R.sub.4 is a C.sub.2 to C.sub.8 alkylene group, preferably a C.sub.2 to C.sub.6 alkylene group, preferably a C.sub.2 to C.sub.4 unbranched alkylene group, more preferably a C.sub.2 to C.sub.3 alkylene or a mixture of C.sub.2 and C.sub.3 alkylene groups (preferably as polyethylene-co-polypropylene oxide blocks) and m is 2 to 150; ##STR2## R'" is selected from a C.sub.1 through C.sub.36 (preferably, C.sub.6 through C.sub.22) linear or branch-chained, cyclic, saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, monomeric or dimeric or an aromatic group, including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl, substituted alkylphenyl or alkylbenzyl group; and R.sub.1 is selected from a C.sub.1 through C.sub.36, preferably a C.sub.2 through C.sub.22 linear or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group, including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl, substituted alkylphenyl or alkylbenzyl group; R.sub.2 is a free electron pair (i.e., R.sub.2 is not substituted, especially where R" is a ##STR3## group), O (to form N-oxide), a hydrogen or a quaternium group, or a mixture of hydrogen and quaternium groups, with the proviso that when R.sub.2 is H and/or a quaternium group, the nitrogen to which said hydrogen or quaternium group is bonded is positively charged and forms a salt with a negatively charged counterion T; R.sub.3 is selected from a C.sub.1 through C.sub.36, preferably a C.sub.2 through C.sub.22, more preferably a C.sub.10 to C.sub.22 linear or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group or an alkylene oxide group (R.sub.4 --O).sub.m where R.sub.4 is a C.sub.2 to C.sub.8 hydrocarbon (alkylene) group, preferably a C.sub.2 to C.sub.6 hydrocarbon (alkylene) group, preferably a C.sub.2 to C.sub.4 unbranched hydrocarbon (alkylene) group, more preferably a C.sub.2 to C.sub.3 or a mixture of C.sub.2 and C.sub.3 (preferably as polyethylene-co-polypropylene oxide blocks) and m is an integer from 2 to 150; each of X and Y is independently selected from a C.sub.1 through C.sub.36, preferably C.sub.1 through C.sub.22, even more preferably C.sub.1 through C.sub.10 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; n is an integer from 1 to 1000, preferably 2 to about 150, even more preferably about 2 to 20, even more preferably about 2-10; and even more preferably about 2 to 4; W is H, a sulfosuccinate group or a C.sub.4 -C.sub.10 alkyl sulfonate group, a phosphate group ##STR4## group where V is a C.sub.1 through C.sub.10 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group and R.sub.5 is a C.sub.1 to C.sub.6 alkyl group or a metal cation selected from the groups consisting of Na+, K+, Ca++ and Mg++ (preferably Na+ or K+). In the compositions described above, R.sub.1 is preferably an unsubstituted saturated or unsaturated branched or unbranched alkyl group, R.sub.2 is preferably O to form an N-oxide with the adjacent nitrogen atom or a hydrogen or quaternium group, R" is preferably a ##STR5## X is preferably a C.sub.1 to C.sub.4 hydrocarbon group and Y is preferably a C.sub.6 to C.sub.22 linear or branch-chained chained saturated or unsaturated hydrocarbon which is even more preferably obtained from a naturally occurring fatty acid most preferably obtained from a plant source which contains a pendant hydroxyl group; R'" is preferably a C.sub.6 to C.sub.22 linear or branch-chained saturated or unsaturated hydrocarbon which is even more preferably obtained from a narturally occurring fatty acid most preferably obtained from a plant source which contains a pendant hydroxyl group; R' is preferably a saturated hydrocarbon containing pendant methyl groups, for example a substituted cyclohexyl group such as an isophorone group and W is most preferably H or a sulfosuccinate group or a related group containing an unsaturated double bond and optionally, an acid moiety (such as maleic acid which can be used to form a sulfosuccinate group) which may be modified to contain a sulfonate group. In the present compositions, the quaternium group R.sub.2 is a carbon containing group (generally, in order to form a quaternium group the nitrogen bonds to a carbon within the quaternium group) preferably selected from C.sub.1 to C.sub.10 alkyl groups, more preferably methyl and ethyl groups, benzyl and alkyl benzyl groups, among numerous others including substituted and unsubstituted saturated and unsaturated hydrocarbon groups including acetate groups (from chloroacetic acid), a propylene glycol group (from epichlorohydrin), ether groups and related groups, among numerous others. Although the counterion T group may be any group which is anionic and is compatible with the chemistry of the present invention, when R.sub.2 is H (the nitrogen to which the H is bonded forms a tertiary ammonium group), preferred T counterion groups include, for example, carboxylates (derived from carboxylic and polycarboxylic acids, preferably dicarboxylic acids, most preferably dicarboxylic acids such as dilinoleic acid, among others), anionic chloride, bromide and iodide, sulfates (mono-, di- and tri-anionic sulfate, preferably tri-anionic sulfate) and phosphates (mono-, di- and tri-anionic, preferably tri-anionic phosphate), among numerous others, with carboxylates and dicarboxylates being particularly preferred. In the case where R.sub.2 is a quaternium group as described generally hereinabove, counterion T is preferably anionic chloride, bromide, iodide, fluoride, sulfate (preferably mono- or di-anionic, preferably alkyl substituted mono-anion such as methyl or ethyl sulfate, more preferably ethyl sulfate, especially where R.sub.3 is an ethyl group) anionic chloride and sulfate (alkyl substituted mono-anionic sulfate) being the preferred counterion T. Monoanionic T groups may be represented by T.sup.-, and dianionic T groups are represented by T.sup.=. Compositions which are representative of ammonium salts or quaternium salts (i.e., where R.sub.2 is H or a quarternium group) according to the present invention described above may be further represented by the structure: ##STR6## Where each of R.sub.1, R.sub.2, R.sub.3, R', R", R'", T, V, W, X, Y and n is the same as described above. Preferred embodiments of ammonium where T is derived from a dicarboxylic acid such as dilinoleic acid and which provide two carboxylate groups or moieties per molecule T, may be represented by the structure: ##STR7## Where T is a dimer dilinoleate dianion. Preferably, each of R.sub.1, R.sub.2, R" and R'" are linear or branched-chain saturated or unsaturated alkyl or alkylene groups which are derived or obtained from fatty acids or fatty amines of natural original, most preferably, fatty amines obtained from plant sources. Preferred hydroxyl containing acids for use in the present invention include ricinleic acid and dimethylolpropionic acid (which allows one to produce a dihydroxyl-substituted fatty amide fatty nd/or fatty amines for use in the present invention include, for example, soyamine, Substituents ("substituted") which may be used in the present compositions may include for example, halogens such as fluorine, chlorine and bromine, nitro groups, amine groups, substituted amine groups, hydroxyl groups, alkoxy groups, unsubstituted and substituted alkoxy groups, alkyl groups or substituted alkyl groups, among numerous others. Preferably, the substitutents in the present compositions are limited to halogen groups, most preferably fluorine and chlorine. One of ordinary skill in the art will be able to recognize modifications which readily may be made to the present compositions to instill desirable characteristics in the present compositions and to avoid undesirable reactions during polymerization such as chain termination, crosslinking and other reactions which may occur with reactive substituents such as hydroxyl groups and amines or amine-containing groups. The groups R.sub.1 and R.sub.3 are preferably derived from such hydroxyl containing natural oils such as castor oil, or from tertiary amines containing alkoxide or alkylene oxide groups, the alkoxide groups preferably being linear and having chain lengths ranging from C.sub.6 through C.sub.22, and the alkylene oxide groups (R.sub.4 --O).sub.m, where R.sub.4 is a C.sub.2 to C.sub.8 alkylene group and m ranges from 2 to 150 wherein a terminal hydroxyl group would be consumed in the reaction with diisocyanate to product a urethane. The tertiary amines could then be reacted to form betaines, amine oxides or salts, with the salts ranging in chain length from C.sub.6 through C.sub.50 carbon atoms. The present invention also relates to compounds of the structure: ##STR8## Where R"" is a ##STR9## group; R.sub.6 is is selected from a C.sub.1 through C.sub.36, preferably a C.sub.2 through C.sub.22, evenmore preferably a C.sub.2 to C.sub.10 linear or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group or an alkylene oxide group (R.sub.4 --O).sub.m where R.sub.4 is a C.sub.2 to C.sub.8 hydrocarbon (alkylene) group, preferably a C.sub.2 to C.sub.6 hydrocarbon (alkylene) group, preferably a C.sub.2 to C.sub.4 unbranched hydrocarbon (alkylene) group, more preferably a C.sub.2 to C.sub.3 or a mixture of C.sub.2 and C.sub.3 (preferably as polyethylene-co-polypropylene oxide blocks) and m is an integer from 2 to 150; Z is H or a C.sub.1 through C.sub.10 linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; and each of R.sub.1, R.sub.2, R.sub.3, R', R", R'", T, V, X, Y and n is the same as described above. Compounds of the present invention where R.sub.2 is H and T is a dianionic species such as dilinoleic acid are clearly contemplated here. Compounds according to the present invention exhibit primary utility as surfactants, wetting agents, anti-irritants, conditioners, viscosity builders in shampoos and liquid hand soaps. In addition, they assist in mending split ends of hair, have low levels of skin, eye and ingestion toxicity and can be used to disperse hair dyes and promote the hair dye function. By selecting the diisocyanate, using the appropriate chain length, taking the degree of unsaturation in the backbone and by adjusting the degree of alkoxylation (judicious use of either ethylene or propylene oxide), it is possible to introduce water solubility/insolubility or emulsification characteristics to the polymer. By building a polymeric surfactant based on urethane technology, it is possible to offer a product that has substantiality to both the skin and hair based on the urethane bonds. Furthermore, adhesion and substantiality of the molecule may be enhanced by the cationic structure of the composition which, in certain embodiments which employs an amine which is converted to the ammonium salt, becomes more cationic with decreasing pH. Additionally, these polymeric urethanes are compatible with a wide array of surfactants that are commonly used in the cosmetic and toiletry industry such as amides, amine oxides, sulfosuccinates, sulfonates, sulfated castor oil, etc., since they share similar backbones. Other properties and characteristics of the compounds of the present invention which make them highly desirable to the cosmetic and toiletry industry are as follows: A. Extremely low order of toxicity and irritation B. Low color C. Low odor D. Excellent compatibility in cosmetic formulations E. Solubility with amides, sulfonates sulfosuccinates, and sulfobetaines F. Nonrancidification G. Coupling characteristics H. Solubility in water, glycols and lower molecular weight alcohols I. Ability to be synthesized to become insoluble in water, glycols and lower molecular alcohols (propoxylated versions) |
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