Compounds derived from polyanhydride resins with film-forming, UV-absorbing, and photostabilizing properties, compositions containing same, and methods of using the same
View Patent ↗Polymers containing one or more fluorene moieties attached to the polymer backbone, sunscreen compositions including a mixture of a photoactive compound and a polymer containing one or more fluorene moieties attached to the polymer backbone are described herein. Also disclosed are methods for stabilizing a sunscreen composition and methods of filtering out ultra-violet light from a substrate by the addition of one or more of the foregoing polymers, and methods of waterproofing and forming a film with one or more of the foregoing polymer are described herein.
1. A polymer comprising monomers selected from the group consisting of a monomer for formula (VII), a monomer of formula (VIII), and combinations thereof:
wherein R 15 and R 19 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; R 16 and R 20 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 17 , R 18 , R 21 and R 22 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; m, l, o and p are each in the range of 0 to 4; k and n are each in the range of 0 to 200, and the sum of k and n is at least 1.
2. The polymer of claim 1 , further comprising a monomer of formula (III), a monomer of formula (IV), a monomer of formula (V), a monomer of formula (VI), and combinations thereof:
wherein R 9 , R 11 , R 13 and R 14 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; R 10 and R 12 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; and g, h, i and j are each in the range of 0 to 200.
3. The polymer of claim 2 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 10 -C 35 alkyl groups.
4. The polymer of claim 3 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 16 , C 18 , and C 22 alkyl groups.
5. The polymer of claim 2 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 3 -C 30 polyether groups.
6. The polymer of claim 5 , wherein R 10 and R 12 are the same and are 2-butoxy-1-ethoxyethane.
7. The polymer of claim 1 , wherein R 16 and R 20 are the same or different and are selected from the group consisting of C 2 -C 15 alkyl groups.
8. The polymer of claim 7 , wherein R 16 and R 20 are the same and are 2,2-dimethylpropane.
9. The polymer of claim 2 , wherein the sum of g and h is at least 1.
10. The polymer of claim 2 , wherein R 9 , R 11 , R 13 , R 14 , R 15 and R 19 are the same or different and are selected from the group consisting of C 5 -C 25 alkyl groups.
11. The polymer of claim 10 , wherein R 9 , R 11 , R 13 , R 14 , R 15 and R 19 are the same and are C 16 straight chain alkyl groups.
12. The polymer of claim 1 , wherein the Weight-Average Molecular Weight of said polymer is in the range of about 30,000 to about 110,000.
13. A sunscreen composition, comprising a mixture of a photoactive compound, and a polymer comprising monomers selected from the group consisting of a monomer for formula (VII), a monomer of formula (VIII), and combinations thereof:
wherein R 15 and R 19 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; R 16 and R 20 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 17 , R 18 , R 21 and R 22 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; m, l, o and p are each in the range of 0 to 4; k and n are each in the range of 0 to 200, and the sum of k and n is at least 1.
14. The composition of claim 13 , wherein said polymer further comprises monomers selected from the group consisting of a monomer of formula (III), a monomer of formula (IV), a monomer of formula (V), a monomer of formula (VI), and combinations thereof:
wherein R 9 , R 11 , R 13 and R 14 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; R 10 and R 12 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; and g, h, i and j are each in the range of 0 to 200.
15. The composition of claim 14 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 10 -C 35 alkyl groups.
16. The composition of claim 15 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 16 , C 18 , and C 22 alkyl groups.
17. The composition of claim 14 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 3 -C 30 polyether groups.
18. The composition of claim 17 , wherein R 10 and R 12 are the same and are 2-butoxy-1-ethoxyethane.
19. The composition of claim 13 , wherein R 16 and R 20 are the same or different and are selected from the group consisting of C 2 -C 15 alkyl groups.
20. The composition of claim 19 , wherein R 16 and R 20 are the same and are 2,2-dimethylpropane.
21. The composition of claim 13 , wherein said polymer is present said composition in an amount in the range of about 0.01% to about 30% by weight of the total weight of the composition.
22. The composition of claim 21 , wherein said polymer is present said composition in an amount in the range of about 0.01% to about 10% by weight of the total weight of the composition.
23. The composition of claim 13 , further comprising a diester or polyester of naphthalene dicarboxylic acid selected from the group consisting of compounds of formulae (XXX) and (XXXI), and combinations thereof:
wherein R 93 and R 94 are the same or different and selected from the group consisting of C 1 -C 22 alkyl groups, diols having the structure HO—R 91 —OH and polyglycols having the structure HO—R 90 —(—O—R 91 —) γ —OH; wherein each R 90 and R 91 is the same or different and selected from the group consisting of C 1 -C 6 straight or branched chain alkyl groups; and wherein α and γ are each in a range of 1 to 100 and β is in a range of 0 to 100.
24. A method of protecting human skin from ultraviolet radiation comprising topically applying to said skin, in a cosmetically acceptable carrier, the composition of claim 13 .
25. A method of protecting a surface from ultraviolet radiation, comprising topically applying to said surface, in a cosmetically acceptable carrier, a polymer comprising monomers selected from the group consisting of a monomer for formula (VII), a monomer of formula (VIII), and combinations thereof:
wherein R 15 and R 19 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; R 16 and R 20 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 17 , R 18 , R 21 and R 22 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; m, l, o and p are each in the range of 0 to 4; k and n are each in the range of 0 to 200, and the sum of k and n is at least 1.
26. The method of claim 25 , wherein said polymer further comprises monomers selected from the group consisting of a monomer of formula (III), a monomer of formula (IV), a monomer of formula (V), a monomer of formula (VI), and combinations thereof:
wherein R 9 , R 11 , R 13 , and R 14 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; R 10 and R 12 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; and g, h, i and j are each in the range of 0 to 200.
27. The method of claim 26 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 10 -C 35 alkyl groups.
28. The method of claim 27 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 16 , C 18 , and C 22 alkyl groups.
29. The method of claim 26 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 3 -C 30 polyether groups.
30. The method of claim 29 , wherein R 10 and R 12 are the same and are 2-butoxy-1-ethoxyethane.
31. The method of claim 25 , wherein R 16 and R 20 are the same or different and are selected from the group consisting of C 2 -C 15 alkyl groups.
32. The method of claim 31 , wherein R 16 and R 20 are the same and are 2,2-dimethylpropane.
33. The method of claim 26 , wherein the sum of g and h is at least 1.
34. The method of claim 25 , wherein said surface comprises human skin.
35. A method of waterproofing a surface, comprising applying a polymer comprising monomers selected from the group consisting of a monomer for formula (VII), a monomer of formula (VIII), and combinations thereof to a selected area of said surface:
wherein R 15 and R 19 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; R 16 and R 20 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 17 , R 18 , R 21 and R 22 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; m, l, o and p are each in the range of 0 to 4; k and n are each in the range of 0 to 200, and the sum of k and n is at least 1.
36. The method of claim 35 , wherein said polymer further comprises monomers selected from the group consisting of a monomer of formula (III), a monomer of formula (IV), a monomer of formula (V), a monomer of formula (VI), and combinations thereof:
wherein R 9 , R 11 , R 13 and R 14 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; R 10 and R 12 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; and g, h, i and j are each in the range of 0 to 200.
37. The method of claim 36 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 10 -C 35 alkyl groups.
38. The method of claim 37 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 16 , C 18 , and C 22 alkyl groups.
39. The method of claim 36 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 3 -C 30 polyether groups.
40. The method of claim 39 , wherein R 10 and R 12 are the same and are 2-butoxy-1-ethoxyethane.
41. The method of claim 35 , wherein R 16 and R 20 are the same or different and are selected from the group consisting of C 2 -C 15 alkyl groups.
42. The method of claim 41 , wherein R 16 and R 20 are the same and are 2,2-dimethylpropane.
43. The method of claim 36 , wherein the sum of g and h is at least 1.
44. A method for forming a film over at least part of a surface, comprising spreading a polymer comprising monomers selected from the group consisting of a monomer for formula (VII), a monomer of formula (VIII), and combinations thereof on said part of said surface:
wherein R 15 and R 19 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; R 16 and R 20 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 17 , R 18 , R 21 and R 22 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; m, l, o and p are each in the range of 0 to 4; k and n are each in the range of 0 to 200, and the sum of k and n is at least 1.
45. The method of claim 44 , wherein said polymer further comprises monomers selected from the group consisting of a monomer of formula (III), a monomer of formula (IV), a monomer of formula (V), a monomer of formula (VI), and combinations thereof:
wherein R 9 , R 11 , R 13 and R 14 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; R 10 and R 12 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; and g, h, i and j are each in the range of 0 to 200.
46. The method of claim 45 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 10 -C 35 alkyl groups.
47. The method of claim 46 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 16 , C 18 , and C 22 alkyl groups.
48. The method of claim 45 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 3 -C 30 polyether groups.
49. The method of claim 48 , wherein R 10 and R 12 are the same and are 2-butoxy-1-ethoxyethane.
50. The method of claim 44 , wherein R 16 and R 20 are the same or different and are selected from the group consisting of C 2 -C 15 alkyl groups.
51. The method of claim 50 , wherein R 16 and R 20 are the same and are 2,2-dimethylpropane.
52. The method of claim 45 , wherein the sum of g and h is at least 1.
53. A method of photostabilizing a dibenzoylmethane derivative, said method comprising the step of, adding to said dibenzoylmethane derivative a photostabilizing amount of a polymer comprising monomers selected from the group consisting of a monomer for formula (VII), a monomer of formula (VIII), and combinations thereof:
wherein R 15 and R 19 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; R 16 and R 20 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 17 , R 18 , R 21 and R 22 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; m, l, o and p are each in the range of 0 to 4; k and n are each in the range of 0 to 200, and the sum of k and n is at least 1.
54. The method of claim 53 , wherein said polymer further comprises monomers selected from the group consisting of a monomer of formula (III), a monomer of formula (IV), a monomer of formula (V), a monomer of formula (VI), and combinations thereof:
wherein R 9 , R 11 , R 13 and R 14 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; R 10 and R 12 are the same or different and are selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 50 polyether, C 1 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkyne; and g, h, i and j are each in the range of 0 to 200.
55. The method of claim 54 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 10 -C 35 alkyl groups.
56. The method of claim 55 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 16 , C 18 , and C 22 alkyl groups.
57. The method of claim 54 , wherein R 10 and R 12 are the same or different and are selected from the group consisting of C 3 -C 30 polyether groups.
58. The method of claim 57 , wherein R 10 and R 12 are the same and are 2-butoxy-1-ethoxyethane.
59. The method of claim 53 , wherein R 16 and R 20 are the same or different and are selected from the group consisting of C 2 -C 15 alkyl groups.
60. The method of claim 59 , wherein R 16 and R 20 are the same and are 2,2-dimethylpropane.
61. The method of claim 54 , wherein the sum of g and h is at least 1.