Organopolysiloxane polymers

• US 10,414,873 B2
• Filed: 01/26/2015
• Issued: 09/17/2019
• Est. Priority Date: 07/29/2013
• Status: Active Grant

• Current Assignee: The Procter & Gamble Company
• Original Assignee: The Procter & Gamble Company
• Inventors: Smith, Steven Daryl, McChain, Robert Joseph, Gizaw, Yonas, Panandiker, Rajan Keshav, Barrera, Carola
• Primary Examiner(s): Zimmer, Marc S
• Application Number:
  US14/604,776
• Publication Number:
  US 20150148511A1
• Time in Patent Office: 1,695 Days
• Field of Search: None
• CPC Class Codes: A61K 2800/10 General cosmetic use
• CPC Class Codes: A61K 2800/5426 cationic
• CPC Class Codes: A61K 8/898 containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• 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 77/385 containing halogens
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C08L 83/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
• CPC Class Codes: C11D 3/3742 Nitrogen containing silicones

Abstract

Inventive organopolysiloxanes and consumer product compositions comprising such organopolysiloxanes. Such compositions can deposit effectively onto target substrates to deliver consumer-desired benefits such as conditioning, anti-wrinkle, softness, and anti-static.

Claims

1. A cationic organopolysiloxane having the formula:

M_wD_xT_yQ_z

wherein;

M=[SiR₁R₂R₃O_1/2], [SiR₁R₂G₁O_1/2], [SiR₁G₁G₂O_1/2], [SiG₁G₂G₃O_1/2], or combinations thereof;

D=[SiR₁R₂O_2/2], [SiR₁G₁O_2/2], [SiG₁G₂O_2/2] or combinations thereof;

T=[SiR₁O_3/2], [SiG₁O_3/2] or combinations thereof;

Q=[SiO_4/2];

w=is an integer from 1 to (2+y+2z);

x=is an integer from 5 to 15,000;

y=is an integer from 0 to 98;

z=is an integer from 0 to 98;

R₁, R₂, and R₃ are each independently selected from the group consisting of H, OH, C₁-C₃₂ alkyl, C₁-C₃₂ substituted alkyl, C₅-C₃₂ aryl, C₅-C₃₂ substituted aryl, C₆-C₃₂ alkylaryl, C₆-C₃₂ substituted alkylaryl, C₁-C₃₂ alkoxy, C₁-C₃₂ substituted alkoxy, C₁-C₃₂ alkylamino, and C₁-C₃₂ substituted alkylamino;

at least one of M, D, or T incorporates at least one moiety G₁, G₂, or G₃; and

G₁, G₂, and G₃ are each independently selected from the formula;

2. The organopolysiloxane according to claim 1 wherein w is an integer from 2 to 50.

3. The organopolysiloxane according to claim 1, wherein each E is independently selected from the group consisting of C₁-C₃₂ alkylene, C₁-C₃₂ substituted alkylene, C₅-C₃₂ arylene, C₅-C₃₂ substituted arylene, C₆-C₃₂ arylalkylene, C₆-C₃₂ substituted arylalkylene, C₁-C₃₂ alkyleneamino, and C₁-C₃₂ substituted alkyleneamino.

4. The organopolysiloxane according to claim 1 having a charge density of from 0.04 meq/g to 4 meq/g.

5. The organopolysiloxane according to claim 1, wherein w is equal to 2.

6. The organopolysiloxane according to claim 1, wherein x is an integer from 10 to 4,000.

7. The organopolysiloxane according to claim 1, wherein x is an integer from 40 to 2,000.

8. The organopolysiloxane according to claim 1, wherein w is equal to 2, x is an integer from 20 to 1,000, and y and z are 0.

9. The organopolysiloxane according to claim 1, wherein each X is a divalent radical independently selected from the group consisting of C₁-C₃₂ alkylene, C₁-C₃₂ substituted alkylene, C₅-C₃₂ arylene, C₅-C₃₂ substituted arylene, C₆-C₃₂ arylalkylene, C₆-C₃₂ substituted arylalkylene, C₁-C₃₂ alkyleneamino, and C₁-C₃₂ substituted alkyleneamino.

10. The organopolysiloxane according to claim 1, wherein each X is a divalent radical independently selected from the group consisting of C₁-C₃₂ alkylene, C₁-C₃₂ substituted alkylene, C₅-C₃₂ arylene, C₅-C₃₂ substituted arylene, C₆-C₃₂ arylalkylene, and C₆-C₃₂ substituted arylalkylene.

11. The organopolysiloxane according to claim 1, wherein A⁻

t is selected from the group consisting of Cl⁻

, Br⁻

, I⁻

, methylsulfate, toluene sulfonate, carboxylate, phosphate, hydroxide, acetate, formate, carbonate, nitrate, and combinations thereof.

12. The organopolysiloxane according to claim 1, wherein A⁻

t is selected from the group consisting of Cl⁻

, Br⁻

, I⁻

, methylsulfate, toluene sulfonate, carboxylate, phosphate and combinations thereof.

13. The organopolysiloxane according to claim 1, wherein each E is a divalent radical independently selected from the group consisting of C₁-C₃₂ alkylene, C₁-C₃₂ substituted alkylene, C₅-C₃₂ arylene, C₅-C₃₂ substituted arylene, C₆-C₃₂ arylalkylene, C₆-C₃₂ substituted arylalkylene C₁-C₃₂ alkyleneamino, and C₁-C₃₂ substituted alkyleneamino.

14. The organopolysiloxane according to claim 1, wherein each E is a divalent radical independently selected from the group consisting of C₁-C₃₂ alkylene, C₁-C₃₂ substituted alkylene, C₅-C₃₂ arylene, C₅-C₃₂ substituted arylene, C₆-C₃₂ arylalkylene, and C₆-C₃₂ substituted arylalkylene.

15. The organopolysiloxane according to claim 1, wherein each E comprises more than 3 carbon atoms.

16. The organopolysiloxane according to claim 1, wherein at least one E is selected from the group consisting of:

17. The organopolysiloxane according to claim 1, wherein at least one E radical is an ethylene radical.

18. The organopolysiloxane according to claim 1, wherein each R₄ is independently selected from the group consisting of H and CH₃.

19. The organopolysiloxane according to claim 1, wherein at least one R₄ is a methyl radical.

20. The organopolysiloxane according to claim 1, wherein for at least one G₁, G₂, or G₃, m is an integer independently selected from 2 to 50.

21. The organopolysiloxane according to claim 1, wherein for at least one G₁, G₂, or G₃, m is an integer independently selected from 2 to 25.

22. The organopolysiloxane according to claim 1, wherein for at least one G₁, G₂, or G₃, m is an integer independently selected from 2 to 10.

23. The organopolysiloxane according to claim 1, wherein for at least one G₁, G₂, or G₃, k is an integer independently selected from 0 to 101.

24. The organopolysiloxane according to claim 1, wherein for at least one G₁, G₂, or G₃, k is an integer independently selected from 2 to 50.

25. The organopolysiloxane according to claim 1, wherein y=z=0.

26. The organopolysiloxane according to claim 1, having a charge density of from 1 meq/g to 12 meq/g.

27. A cationic organopolysiloxane having the formula:

M_wD_xT_yQ_z

wherein;

M=[SiR₁R₂R₃O_1/2], [SiR₁R₂G₁O_1/2], [SiR₁G₁G₂O_1/2], [SiG₁G₂G₃O_1/2], or combinations thereof;

D=[SiR₁R₂O_2/2], [SiR₁G₁O_2/2], [SiG₁G₂O_2/2] or combinations thereof;

T=[SiR₁O_3/2], [SiG₁O_3/2] or combinations thereof;

Q=[SiO_4/2];

w=is an integer from 1 to (2+y+2z);

x=is an integer from 5 to 15,000;

y=is an integer from 0 to 98;

z=is an integer from 0 to 98;

R₁, R₂, and R₃ are each independently selected from the group consisting of H, OH, C₁-C₃₂ alkyl, C₁-C₃₂ substituted alkyl, C₅-C₃₂ aryl, C₅-C₃₂ substituted aryl, C₆-C₃₂ alkylaryl, C₆-C₃₂ substituted alkylaryl, C₁-C₃₂ alkoxy, C₁-C₃₂ substituted alkoxy, C₁-C₃₂ alkylamino, and C₁-C₃₂ substituted alkylamino;

at least one of M, D, or T incorporates at least one moiety G₁, G₂, or G₃; and

G₁, G₂, and G₃ are each independently selected from the formula;

28. The organopolysiloxane according to claim 27 wherein w is an integer from 2 to 50.

29. The organopolysiloxane according to claim 27, wherein each E is independently selected from the group consisting of C₄-C₃₂ alkylene, C₄-C₃₂ substituted, alkylene, C₅-C₃₂ arylene, C₅-C₃₂ substituted arylene, C₆-C₃₂ arylalkylene, C₆-C₃₂ substituted arylalkylene, C₄-C₃₂ alkyleneamino, and C₄-C₃₂ substituted alkyleneamino, ring-opened epoxide, and ring-opened glycidyl.

30. The organopolysiloxane according to claim 27 having a charge density of from 0.04 meq/g to 12 meq/g.

31. The organopolysiloxane according to claim 27 having a charge density of from 0.04 meq/g to 4 meq/g.

32. The organopolysiloxane according to claim 27 having a charge density of from 1 meq/g to 12 meq/g.

33. The organopolysiloxane according to claim 27, wherein w is equal to 2.

34. The organopolysiloxane according to claim 27, wherein x is an integer from 10 to 4,000.

35. The organopolysiloxane according to claim 27, wherein x is an integer from 40 to 2,000.

36. The organopolysiloxane according to claim 27, wherein w is equal to 2, x is an integer from 20 to 1,000, and y and z are 0.

37. The organopolysiloxane according to claim 27, wherein each X is a divalent radical independently selected from the group consisting of C₁-C₃₂ alkylene, C₁-C₃₂ substituted alkylene, C₅-C₃₂ arylene, C₅-C₃₂ substituted arylene, C₆-C₃₂ arylalkylene, C₆-C₃₂ substituted arylalkylene, C₁-C₃₂ alkyleneamino, and C₁-C₃₂ substituted alkyleneamino.

38. The organopolysiloxane according to claim 27, wherein each X is a divalent radical independently selected from the group consisting of C₁-C₃₂ alkylene, C₁-C₃₂ substituted alkylene, C₅-C₃₂ arylene, C₅-C₃₂ substituted arylene, C₆-C₃₂ arylalkylene, and C₆-C₃₂ substituted arylalkylene.

39. The organopolysiloxane according to claim 27, wherein A⁻

t is selected from the group consisting of Cl⁻

, Br⁻

, I⁻

, methylsulfate, toluene sulfonate, carboxylate, phosphate, hydroxide, acetate, formate, carbonate, nitrate, and combinations thereof.

40. The organopolysiloxane according to claim 27, wherein A⁻

t is selected from the group consisting of Cl⁻

, Br, I⁻

, methylsulfate, toluene sulfonate, carboxylate, phosphate and combinations thereof.

41. The organopolysiloxane according to claim 27, wherein each E is a independently selected from the group consisting of C₄-C₃₂ alkylene, C₄-C₃₂ substituted, alkylene, C₅-C₃₂ arylene, C₅-C₃₂ substituted arylene, C₆-C₃₂ arylalkylene, C₆-C₃₂ substituted arylalkylene, C₄-C₃₂ alkyleneamino, and C₄-C₃₂ substituted alkyleneamino.

42. The organopolysiloxane according to claim 27, wherein each E is a independently selected from the group consisting of C₄-C₃₂ alkylene, C₄-C₃₂ substituted, alkylene, C₅-C₃₂ arylene, C₅-C₃₂ substituted arylene, C₆-C₃₂ arylalkylene, and C₆-C₃₂ substituted arylalkylene.

43. The organopolysiloxane according to claim 27, wherein at least one E is selected from the group consisting of:

44. The organopolysiloxane according to claim 27, wherein each R₄ is independently selected from the group consisting of H and CH₃.

45. The organopolysiloxane according to claim 27, wherein at least one R₄ is a methyl radical.

46. The organopolysiloxane according to claim 27, wherein for at least one G₁, G₂, or G₃, m is an integer independently selected from 2 to 50.

47. The organopolysiloxane according to claim 27, wherein for at least one G₁, G₂, or G₃, m is an integer independently selected from 2 to 25.

48. The organopolysiloxane according to claim 27, wherein for at least one G₁, G₂, or G₃, m is an integer independently selected from 2 to 10.

49. The organopolysiloxane according to claim 27, wherein for at least one G₁, G₂, or G₃, k is an integer independently selected from 0 to 101.

50. The organopolysiloxane according to claim 27, wherein for at least one G₁, G₂, or G₃, k is an integer independently selected from 2 to 50.

51. The organopolysiloxane according to claim 27, wherein y=z=0.