Polyether siloxane copolymer network compositions

• US 6,531,540 B1
• Filed: 05/16/2001
• Issued: 03/11/2003
• Est. Priority Date: 05/16/2001
• Status: Expired due to Term

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: OʼBrien, Michael J.
• Primary Examiner(s): Moore, Margaret G.
• Assistant Examiner(s): Zimmer, Marc S
• Application Number:
  US09/858,424
• Time in Patent Office: 664 Days
• Field of Search: 528/27, 528/31, 528/403, 524/379, 524/386, 524/387, 524/806
• US Class Current: 524/806
• CPC Class Codes: A61K 8/894 modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
• CPC Class Codes: A61K 8/895 containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• CPC Class Codes: A61Q 1/06 Lipsticks
• CPC Class Codes: A61Q 15/00 Anti-perspirants or body deodorants deodorisation of air A61L9/00
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/001 Preparations for care of the lips
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: A61Q 5/12 Preparations containing hair conditioners
• CPC Class Codes: C08G 77/14 containing silicon bound to oxygen-containing groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/38 Polysiloxanes modified by chemical after-treatment C08G77/045 takes precedence
• CPC Class Codes: C08L 83/06 containing silicon bound to oxygen-containing groups C08L83/12 takes precedence

Abstract

A composition comprising the reaction products of

M_aM^H_bM^E_cD_dD^H_eD^E_fT_gT^H_hT^E_iQ_j

where

M=R¹R²R³SiO_1/2;

M^H=R⁴R⁵HSiO_1/2;

M^E=R⁶R⁷R^ESiO_1/2;

D=R⁸R⁹SiO_2/2;

D^H=R¹⁰HSiO_2/2;

D^E=R¹¹R^ESiO_2/2;

T=R¹²SiO_3/2;

T^H=HSiO_3/2;

T^E=R^ESiO_3/2; and

Q=SiO_4/2;

where R¹, R², R³, R⁸, R⁹ and R¹² are independently monovalent hydrocarbon radicals having from one to sixty carbon atoms; R⁴, R⁵ and R¹⁰ are independently monovalent hydrocarbon radicals having from one to sixty carbon atoms or hydrogen; R⁶, R⁷, R¹¹ are independently monovalent hydrocarbon radicals having from one to sixty carbon atoms or R^E; each R^E is independently a monovalent hydrocarbon radical containing one or more oxirane moieties having from one to sixty carbon atoms; the stoichiometric subscripts a, b, c, d, e, f, g, h, i, and j are either zero or positive subject to the following limitations: a+b+c>1; b+e+h>1; c+f+i>1; b+e+h>c+f+i; and when d+e+f+g+h+i+j=0, a+b+c=2. In a preferred embodiment the reaction product of the present invention is a polyether siloxane copolymer network. In another preferred embodiment embodiment the reaction product of the present invention is a polyether siloxane copolymer network swollen with a volatile low molecular weight silicon containing compound. These compositions are useful for a variety of personal care compositions.

Claims

1. A composition comprising the reaction product of:

2. The composition of claim 1 where R^E has the formula:

where R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are each independently selected from the group of hydrogen and monovalent hydrocarbon radicals having from one to sixty carbon atoms, Q_m is a di- or trivalent hydrocarbon radical having from one to sixty carbon atoms, Q_n is a divalent hydrocarbon radical having from one to sixty carbon atoms with the subscripts m and n independently zero or one subject to the limitation that when Qm is trivalent R¹⁴ is absent and Q_m forms a bond with the carbon bearing R¹³.

3. The composition of claim 1 where R^E is obtained by hydrosilylation of a compound selected from the group consisting of 4vinyl cyclohexene oxide, allyl glycidyl ether, limonene oxide, 1,2-epoxy-5hexene, 1,2epoxy-7-octene, norbornadiene monoepoxide and 1,2-epoxy-9-decene.

4. The composition of claim 2 where R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are hydrogen and m and n are zero.

5. The composition of claim 3 where R^E is 4-vinyl cyclohexene oxide.

6. The composition of claim 1 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl, C30+ and 3,3,3-fluoropropyl.

7. The composition of claim 2 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

8. The composition of claim 3 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

9. The composition of claim 4 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

10. The composition of claim 5 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

11. An aqueous emulsion where the discontinuous phase comprises water and the continuous phase comprises a composition comprising the reaction product of:

12. The composition of claim 11 where R^E has the formula:

where R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are each independently selected from the group of hydrogen and monovalent hydrocarbon radicals having from one to sixty carbon atoms, Q_m is a di- or trivalent hydrocarbon radical having from one to sixty carbon atoms, Q_n is a divalent hydrocarbon radical having from one to sixty carbon atoms with the subscripts m and n independently zero or one subject to the limitation that when Qm is trivalent R¹⁴ is absent and Q_m forms a bond with the carbon bearing R¹³.

13. The composition of claim 11 where R^E is obtained by hydrosilylation of a compound selected from the group consisting of 4-vinyl cyclohexene oxide, allyl glycidyl ether, limonene oxide, 1,2-epoxy-5-hexene, 1,2-epoxy-7-octene, norbornadiene monoepoxide and 1,2-epoxy-9-decene.

14. The composition of claim 12 where R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are hydrogen and m and n are zero.

15. The composition of claim 13 where R^E is 4-vinyl cyclohexene oxide.

16. The composition of claim 11 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl, C30+ and 3,3,3-fluoropropyl.

17. The composition of claim 12 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

18. The composition of claim 13 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

19. The composition of claim 14 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

20. The composition of claim 15 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

21. An aqueous emulsion where the continuous phase comprises water :

and the discontinuous phase comprises a composition comprising the reaction product of;

22. The composition of claim 21 where R^E has the formula:

where R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are each independently selected from the group of hydrogen and monovalent hydrocarbon radicals having from one to sixty carbon atoms, Q_m is a di- or trivalent hydrocarbon radical having from one to sixty carbon atoms, Q_n is a divalent hydrocarbon radical having from one to sixty carbon atoms with the subscripts m and n independently zero or one subject to the limitation that when Qm is trivalent R¹⁴ is absent and Q_m forms a bond with the carbon bearing R¹³.

23. The composition of claim 21 where R^E is obtained by hydrosilylation of a compound selected from the group.consisting of 4-vinyl cyclohexene oxide, allyl glycidyl ether, limonene oxide, 1,2-epoxy-5-hexene, 1,2-epoxy-7-octene, norbornadiene monoepoxide and 1,2-epoxy-9-decene.

24. The composition of claim 22 where R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are hydrogen and m and n are zero.

25. The composition of claim 23 where R^E is 4-vinyl cyclohexene oxide.

26. The composition of claim 21 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl, C30+ and 3,3,3-fluoropropyl.

27. The composition of claim 22 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

28. The composition of claim 23 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

29. The composition of claim 24 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

30. The composition of claim 25 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

31. A non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic solvent and the continuous phase comprises a composition comprising the reaction product of:

32. The composition of claim 31 where R^E has the formula:

where R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are each independently selected from the group of hydrogen and monovalent hydrocarbon radicals having from one to sixty carbon atoms, Q_m is a di- or trivalent hydrocarbon radical having from one to sixty carbon atoms, Q_n is a divalent hydrocarbon radical having from one to sixty carbon atoms with the subscripts m and n independently zero or one subject to the limitation that when Qm is trivalent R¹⁴ is absent and Q_m forms a bond with the carbon bearing R¹³.

33. The composition of claim 31 where R^E is obtained by hydrosilylation of a compound selected from the group consisting of 4vinyl cyclohexene oxide, allyl glycidyl ether, limonene oxide, 1,2-epoxy-5-hexene, 1,2-epoxy-7-octene, norbornadiene monoepoxide and 1,2-epoxy-9-decene.

34. The composition of claim 32 where R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are hydrogen and m and n are zero.

35. The composition of claim 33 where R^E is 4-vinyl cyclohexene oxide.

36. The composition of claim 31 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl, C30+ and 3,3,3-fluoropropyl.

37. The composition of claim 32 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

38. The composition of claim 33 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

39. The composition of claim 34 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

40. The composition of claim 35 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

41. A non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic solvent and the discontinuous phase comprises a composition comprising the reaction product of:

42. The composition of claim 41 where R^E has the formula:

where R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are each independently selected from the group of hydrogen and monovalent hydrocarbon radicals having from one to sixty carbon atoms, Q_m is a di- or trivalent hydrocarbon radical having from one to sixty carbon atoms, Q_n is a divalent hydrocarbon radical having from one to sixty carbon atoms with the subscripts m and n independently zero or one subject to the limitation that when Qm is trivalent R¹⁴ is absent and Q_m forms a bonds with the carbon bearing R¹³.

43. The composition of claim 41 where R^E is obtained by hydrosilylation of a compound selected from the group consisting of 4-vinyl cyclohexene oxide, allyl glycidyl ether, limonene oxide, 1,2-epoxy-5-hexene, 1,2-epoxy-7-octene, norbornadiene monoepoxide and 1,2-epoxy-9-decene.

44. The composition of claim 42 where R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are hydrogen and m and n are zero.

45. The composition of claim 43 where R^E is 4-vinyl cyclohexene oxide.

46. The composition of claim 41 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl, C30+ and 3,3,3-fluoropropyl.

47. The composition of claim 42 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

48. The composition of claim 43 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

49. The composition of claim 44 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.

50. The composition of claim 45 where R¹, R², R³, R⁸, R⁹ and R¹² are independently selected from the group consisting of methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, ethenyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecanyl, carboxymethyl, chloromethyl and 3,3,3-fluoropropyl.