Polymers Containing Silicone Copolyol Macromers and Personal Care Compositions Containing Same

Abstract

Dimethicone copolyol polymers are synthesized from dimethicone copolyol macromers. Polymers containing the macromer repeating units are useful in a variety of applications including personal care, textile and industrial formulations to deliver softness, lubricity, fixative, humidity resistance, water repellency, gloss, surface modification, and surfactant properties.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a photograph of a Caucasian hair mannequin head in which one half of the head is styled with a hair fixative composition containing a polymer of the invention and the other half of the head is styled with a control fixative composition. The photograph is taken before humidity chamber exposure.

FIG. 1A is a photograph of an Asian hair mannequin head in which one half of the head is styled with a hair fixative composition containing a polymer of the invention and the other half of the head is styled with a commercial fixative composition. The photograph is taken before humidity chamber exposure.

FIG. 2 is a photograph of the Caucasian hair mannequin head illustrated in FIG. 1 taken after 1 hour in a humidity chamber set at 35° C. and 90% relative humidity.

FIG. 2A is a photograph of the Asian hair mannequin head illustrated in FIG. 1A taken after 1 hour in a humidity chamber set at 35° C. and 90% relative humidity.

FIG. 3 is a photograph of the Caucasian hair mannequin head illustrated in FIG. 1 taken after 2 hours in a humidity chamber set at 35° C. and 90% relative humidity.

FIG. 3A is a photograph of the Asian hair mannequin head illustrated in FIG. 1A taken after 2 hours in a humidity chamber set at 35° C. and 90% relative humidity.

FIG. 4 is a photograph of the Caucasian hair mannequin head illustrated in FIG. 1 taken after 3 hours in a humidity chamber set at 35° C. and 90% relative humidity.

FIG. 4A is a photograph of the Asian hair mannequin head illustrated in FIG. 1A taken after 3 hours in a humidity chamber set at 35° C. and 90% relative humidity.

FIG. 5 is a photograph of the measuring apparatus utilized in the High Humidity Stiffness Curl Retention Test (HHSR) showing the hair swatch mounting stand with graduated measurement scale in the background.

Claims

1. A composition comprising: A) A polymer polymerized from a monomer composition comprising at least one dimethicone copolyol macromer selected from formulae III and IV:

2. A composition of claim 1 wherein said monomer composition further comprises at least one monomer selected from: a) at least one non-ionic vinyl monomer;b) at least one acidic vinyl monomer;c) at least one cationic vinyl monomer;d) at least one associative vinyl monomer;e) at least one semihydrophobic vinyl monomer;f at least one crosslinking monomer; and mixtures thereof.

3. A composition of claim 2 wherein said non-ionic vinyl monomer is selected from at least one monomer represented by the formulae: CH2═C(X)Z;CH2═CH—OC(O)R7 wherein, X is H or methyl; and Z is —C(O)OR8, —C(O)NH2, —C(O)NHR8, —C(O)N(R8)2, —C6H4R8, —C6H4OR8, —C6H4Cl, —C6H11, —C6H7(R8)(R8)(R8), —CN, —NHC(O)CH3, —NHC(O)H, N-(2-pyrrolidonyl), N-caprolactamyl, —C(O)NHC(CH3)3, —C(O)NHCH2CH2—N-ethyleneurea, —Si(R7)3, —C(O)O(CH2)xSi(R7)3, —C(O)NH(CH2)xSi(R7)3, or —(CH2)xSi(R7)3; x is an integer ranging from about 1 to about 6; R7 independently represents linear and branched C1 to C18 alkyl; R8 independently represents linear and branched C1 to C30 alkyl, hydroxy substituted C2 to C30 alkyl, and halogen substituted C1 to C30 alkyl.

4. A composition of claim 2 wherein said acidic vinyl monomer contains at least one acidic group selected from a carboxylic acid group and salts thereof, a sulfonic acid group and salts thereof, and a phosphonic acid group and salts thereof.

5. A composition of claim 4 wherein said acidic vinyl monomer is selected from acrylic acid, methacrylic acid, itaconic acid, citraconic acid, maleic acid, fumaric acid, crotonic acid, aconitic acid, C1 to C18 alkyl monoesters of maleic, fumaric, itaconic, or aconitic acid, anhydrides of dicarboxylic acids, vinyl sulfonic acid, 2-sulfoethyl methacrylate, styrene sulfonic acid, 2-acrylamido-2-methylpropane sulfonic acid, allyloxybenzene sulfonic acid, vinyl phosphonic acid, allyl phosphonic acid, 3-acrylamidopropyl phosphonic acid; and salts thereof; and mixtures thereof.

6. A composition of claim 1 wherein said cationic vinyl monomer is selected from mono-(C1 to C4)alkylamino(C1 to C8)alkyl (meth)acrylate, a di-(C1 to C4)alkylamino(C1 to C8)alkyl (meth)acrylate, a mono-(C1 to C4)alkylamino(C1 to C8)alkyl (meth)acrylamide, a di-(C1 to C4)alkylamino(C1 to C8)alkyl (meth)acrylamide, a nitrogen-containing heterocyclic (meth)acrylamide, a nitrogen-containing heterocyclic (meth)acrylate; and salts thereof; and mixtures thereof.

7. A composition of claim 6 wherein said cationic vinyl monomer is selected from 2-(N,N-dimethylamino)ethyl (meth)acrylate, 3-(N,N-dimethylamino)propyl (meth)acrylate, 4-(N,N-dimethylamino)butyl (meth)acrylate, (N,N-dimethylamino)-t-butyl(meth)acrylate, 2-tert-butylamino)ethyl methacrylate, 2-(N,N-diethylamino)ethyl (meth)acrylate, 3-(N,N-diethylamino)propyl(meth)acrylate, 2-N,N-dimethylamino)neopentyl acrylate, 4-N,N-diethylamino)butyl(meth)acrylate, 2-(N,N-dipropylamino)ethyl (meth)acrylate, 3-N,N-dipropylamino)propyl (meth)acrylate, 4-N,N-dipropylamino)butyl (meth)acrylate, 3-(N,N-dimethylamino)propyl (meth)acrylate, 2-(4-morpholinyl)ethyl methacrylate, 2-(4-morpholinyl)ethyl acrylate, N′-(2-N,N-dimethylamino)ethyl methacrylamide, 2-N,N-dimethylamino)propyl methacrylamide, N′-3-N,N-dimethylamino)propyl (meth)acrylamide, N-(2-pyridyl)acrylamide, N-2-imidazoyl)(meth)acrylamide, N-(4-morpholinyl) (meth)acrylamide, N-4-morpholinyl)acrylamide, 2-vinyl pyridine, 4-vinyl pyridine, N-vinyl-2-methylimidazole, N-vinylimidazole, N-vinyl-4-methylimidazole, and N-vinyloxazolidone; and salts thereof; and mixtures thereof.

8. A composition of claim 5 wherein said cationic vinyl monomer is selected from 3-trimethylammonium propyl methacrylamide chloride, 3-trimethylammonium propyl acrylamide chloride, quaternized N,N-dimethylaminoethyl methacrylate with C1 to C30 alkyl sulphate, quaternized N,N-dimethylaminoethyl methacrylate with methylchloride, quaternized vinyl imidazole, methacryloyl ethyl betaine, and methacryloyl N-oxide.

9. A composition of claim 1 wherein said associative vinyl monomer is selected from at least one monomer represented by the formula:

10. A composition of claim 9 wherein said associative vinyl monomer is selected from cetyl polyethoxylated methacrylate, cetearyl polyethoxylated methacrylate, stearyl polyethoxylated (meth)acrylate, arachidyl polyethoxylated (meth)acrylate, behenyl polyethoxylated methacrylate, lauryl polyethoxylated methacrylate, cerotyl polyethoxylated (meth)acrylate, montanyl polyethoxylated (meth)acrylate, melissyl polyethoxylated (meth)acrylate, lacceryl polyethoxylated (meth)acrylate, tristyryl phenolpolyethoxylated methacrylate, hydrogenated castor oil polyethoxylated methacrylate, canola polyethoxylated (meth)acrylate, and cholesterol polyethoxylated methacrylate, wherein the polyethoxylated portion of the monomer contains from about 5 to about 100 ethylene oxide repeating units.

11. A composition of claim 1 wherein said semihydrophobic vinyl monomer is selected from at least one monomer represented by the formula:

12. A composition of claim 11 wherein said semihydrophobic vinyl monomer is represented by at least one monomer of the formulae: CH2═CH—O(CH2)aO(C3H6O)b(C2H4O)cHCH2═CH—CH2O(C3H6O)d(C2H4O)eHwherein a is an integer of 2, 3, or 4; b is an integer in the range of 1 to about 10; c is an integer in the range of about 5 to about 50; d is an integer in the range of 1 to about 10; and e is an integer in the range of about 5 to about 50.

13. A composition of claim 1 wherein said monomer composition comprises 0 to 5 weight percent (based on the weight of the total monomers of a crosslinking monomer.

14. A composition of claim 1 wherein said monomer composition comprises at least 0.01 percent by weight based on the total monomer weight of a chain transfer agent.

15. A composition of claim 1 wherein said composition comprises an ingredient selected from a structurant(s), a humectant(s), an emollient(s), a fixative(s), a surfactant(s), a rheology modifier(s), a neutralizer(s), a conditioner, and combinations thereof.

16. The composition of claim 15 wherein said composition further comprises an ingredient selected form an auxiliary solvent, a propellant, and combinations thereof.

17. The composition of claim 16 wherein said composition is in the form of a cream, pomade, gel, paste, ointment, spray, lotion, spritz, and mousse.

18. A hair care composition comprising: A) A polymer polymerized from a monomer composition comprising:(i) at least one dimethicone copolyol macromer selected from formulae III and IV:

19. A hair care composition of claim 18 wherein said structurant is selected from at least one wax, at least one fatty alcohol and esters thereof, at least one fatty acid and esters thereof, petrolatum, and combinations thereof.

20. A hair care composition of claim 18 wherein said composition is in the form of a cream, gel, pomade, paste, mousse, spray, or spritz.

21. A hair care composition of claim 18 wherein said acidic vinyl monomer is selected from acrylic acid, methacrylic acid, itaconic acid, citraconic acid, maleic acid, fumaric acid, crotonic acid, aconitic acid, C1 to C18 alkyl monoesters of maleic, fumaric, itaconic, or aconitic acid, anhydrides of dicarboxylic acids, vinyl sulfonic acid, 2-sulfoethyl methacrylate, styrene sulfonic acid, 2-acrylamido-2-methylpropane sulfonic acid, allyloxybenzene sulfonic acid, vinyl phosphonic acid, allyl phosphonic acid, 3-acrylamidopropyl phosphonic acid; and salts thereof; and mixtures thereof.

22. A hair care composition of claim 18 wherein said nonionic vinyl monomer is selected from C1 to C30 alkyl (meth)acrylates, cyclohexyl(meth)acrylates, 3,3,5-trimethylcyclohexyl(meth)acrylates, C1 to C30 alkyl (meth)acrylamides, styrene, vinyl toluene butyl styrene, isopropyl styrene, p-chloro styrene, vinyl acetate, vinyl butyrate, vinyl caprolate, vinyl pivalate, vinyl neodecanoate, methacrylonitrile, acrylonitrile, trimethylvinylsilane, dimethylethylvinylsilane, allyldimethylphenylsilane, allyltrimethylsilane, 3-acrylamidopropyltrimethylsilane, 3-trimethylsilylpropyl methacrylate, 2-hydroxyethyl methacrylate (HEMA), 2-hydroxyethyl acrylate (2-HEA), 3-hydroxypropyl acrylate, glycerol mono(meth)acrylate; tris(hydroxymethyl)ethane mono(meth)acrylate, pentaerythritol mono(meth)acrylate, N-hydroxymethyl (meth)acrylamide, 2-hydroxyethyl (meth)acrylamide, 3-hydroxypropyl (meth)acrylamide, (meth)acrylamide, t-octyl(meth)acrylamide, N-(2,3-dihydroxypropyl) acrylamide, t-butyl(meth)acrylamide, N-vinyl caprolactam, N-vinyl pyrrolidone, methacrylamidoethyl-N-ethyleneurea, methoxyethyl (meth)acrylate, 2-(2-ethoxyethoxy)ethyl (meth)acrylate; and mixtures thereof.

23. A hair care composition of claim 18 wherein said associative vinyl monomer is selected from at least one monomer represented by the formula:

24. A composition of claim 23 wherein said associative vinyl monomer is selected from cetyl polyethoxylated methacrylate, cetearyl polyethoxylated methacrylate, stearyl polyethoxylated (meth)acrylate, arachidyl polyethoxylated (meth)acrylate, behenyl polyethoxylated methacrylate, lauryl polyethoxylated methacrylate, cerotyl polyethoxylated (meth)acrylate, montanyl polyethoxylated (meth)acrylate, melissyl polyethoxylated (meth)acrylate, lacceryl polyethoxylated (meth)acrylate, tristyryl phenolpolyethoxylated methacrylate, hydrogenated castor oil polyethoxylated methacrylate, canola polyethoxylated (meth)acrylate, and cholesterol polyethoxylated methacrylate, wherein the polyethoxylated portion of the monomer contains from about 5 to about 100 ethylene oxide repeating units.