Silicone modified fatty acids, method of preparation and usage thereof
View Patent ↗The present invention relates to silicone modified fatty carboxylic acid compounds. More specifically, the present invention relates to low molecular weight, i.e., short chain, silicone modified fatty carboxylic acids, their use and method of making same. The present invention provides silicone compounds partially derived from natural products for use in cosmetic formulations.
1. A modified silicone compound comprising the reaction product of:
a) at least one cyclic ether silicone having the formula:
M a M A b D c D B d T e T C f Q g
wherein;
M=R 1 R 2 R 3 Si0 1/2
M A =R 4 R 5 R 6 SiO 1/2
D=R 7 R 8 SiO 1/2
D B =R 9 R 10 SiO 2/2
T=R 11 SiO 3/2
T C =R 12 SiO 3/2 ;
Q=SiO 4/2 ;
R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having from 1 to 6 carbon atoms; R 4 , R 9 , and R 12 are each independently a monovalent hydrocarbon radical containing from 3 to 25 carbon atoms and possessing at least one epoxy or oxetane group; wherein subscripts a, b, c, d, e, f, and g are zero or positive and their sum is not greater than 25, with the proviso that at least one of subscripts b, d, and f is positive and c+d is from 1 to 5; and,
b) at least one substantially pure saturated fatty carboxylic acid.
2. The silicone compound of claim 1 wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having from 1 to 3 carbon atoms.
3. The silicone compound of claim 1 wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having 1 carbon atom.
4. The silicone compound of claim 1 wherein the sum of subscripts a, b, c, d, e, f, and g is not greater than 20.
5. The silicone compound of claim 4 wherein subscript b is zero, subscript a is 1 to 3, subscripts c, e, and g are zero or less than 3, and at least one of subscript d and f is positive.
6. The silicone compound of claim 4 wherein subscript b is zero, subscript a is 2, subscripts c, e, f, and g are zero and d is 1.
7. The silicone compound of claim 1 wherein the cyclic ether silicone is at least one selected from the group consisting of 3,4-epoxycyclohexyl-1-ethyl-heptamethyltrisiloxane; 1,1,1,3,5,5,5-heptamethyl-3-[2-(7-oxa-bicyclo[4.1.0]hept-3-yl)-ethyl]-tri-siloxane; 1,1,3,3,5,5,5-heptamethyl-1-[2-(7-oxa-bicyclo[4.1.0]hept-3-yl)-e-thyl]-trisiloxane; bisethylcyclohexyloxidepolysiloxane; 1,1,1,3,5,5,5-heptamethyl-3-[2-(1-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-p-ropyl]-trisiloxane; and 1,1,1,3,5,5,5-heptamethyl-3-oxiranylmethoxy-propyl-trisiloxane.
8. The silicone compound of claim 1 wherein the fatty carboxylic acid is at least one selected from the group of naturally derived fatty carboxylic acids and synthetic fatty carboxylic acid.
9. The silicone compound of claim 1 wherein the fatty carboxylic acid is a hydrocarbon radical containing at least one carboxylic acid group and having from 2 to 34 carbon atoms.
10. The silicone compound of claim 1 wherein the fatty carboxylic acids is at least one selected from the group consisting of palmitic acid, myristic acid, stearic acid, behenic acid and caprylic acid.
11. The silicone compound of claim 1 wherein the amount of cyclic ether silicone compound used in the reaction is from about the stoichiometric equivalent, where there is not more than 1 epoxy or oxetane group per 1 carboxylic acid group.
12. The silicone compound of claim 1 wherein the amount of cyclic ether silicone compound used in the reaction is from about 1:1 to 1:10 cyclic ether silicone/fatty acid stoichiometric ratio.
13. A product comprising the modified silicone compound of claim 1 and at least one product ingredient.
14. The product of claim 13 wherein the product ingredient is at least one selected from the group consisting of ester waxes, oils and fats of animal or vegetable origin, fatty alcohols, fatty acids, alkyl esters of fatty acids, hydrocarbon oils and waxes, water, organic solvents, surfactants, oil-soluble vitamins, water-soluble vitamins, oil-soluble drugs, water-soluble drugs, actives, pharmaceutical acceptable carriers and pharmaceutical compounds.
15. A product containing the silicone compound of claim 1 chosen from pharmaceutical compositions, medicinal and therapeutic compositions for pharmaceutical purposes and delivery systems for oil and water soluble substances.
16. A pharmaceutical composition comprising a modified silicone compound of claim 1 and at least one pharmaceutical acceptable carrier.
17. The compound of claim 1 wherein e, f and g are equal to zero, c+d are equal to 1, and a+b are equal to 2, with the proviso that at b+d is at least 1.
18. The compound of claim 1 wherein subscript d is equal to at least 1.
19. The compound of claim 1 wherein R 4 , R 9 , and R 12 are each independently a monovalent hydrocarbon radical containing from 3 to 25 carbon atoms and possessing at least one oxetane group.
20. A method for producing a modified silicone compound comprising:
i) reacting at least one cyclic ether silicone having the formula:
M a M A b D c D B d T e T C f Q g
wherein;
M=R 1 R 2 R 3 Si0 1/2
M A =R 4 R 5 R 6 SiO 1/2
D=R 7 R 8 SiO 1/2
D B =R 9 R 10 SiO 2/2
T=R 11 SiO 3/2
T C =R 12 SiO 3/2 ;
Q=SiO 4/2 ;
R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having from 1 to 6 carbon atoms; R 4 , R 9 , and R 12 are each independently a monovalent hydrocarbon radical containing from 3 to 25 carbon atoms and possessing at least one epoxy or oxetane group; wherein subscripts a, b, c, d, e, f, and g are zero or positive and their sum is not greater than 25, with the proviso that at least one of subscripts b, d, and f is positive and c+d is from 1 to 5; with at least one substantially pure fatty carboxylic acid, in the presence of at least one catalyst.
21. The method of claim 20 wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having from 1 to 3 carbon atoms.
22. The method of claim 20 wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having 1 carbon atom.
23. The method of claim 20 wherein the sum of subscripts a, b, c, d, e, f, and g is not greater than 20.
24. The method of claim 23 wherein subscript b is zero, subscript a is 1 to 3, subscripts c, e, and g are zero or less than 3, and at least one of subscript d and f is positive.
25. The method of claim 23 wherein subscript b is zero, subscript a is 2, subscripts c, e, f, and g are zero and d is 1.
26. The method of claim 20 wherein the cyclic ether silicone is at least one selected from the group consisting of 3,4-epoxycyclohexyl-1-ethyl-heptamethyltrisiloxane; 1,1,1,3,5,5,5-heptamethyl-3-[2-(7-oxa-bicyclo[4.1.0]hept-3-yl)-ethyl]-tri-siloxane; 1,1,3,3,5,5,5-heptamethyl-1-[2-(7-oxa-bicyclo[4.1.0]hept-3-yl)-ethyl]-trisiloxane; bisethylcyclohexyloxidepolysiloxane; 1,1,1,3,5,5,5-heptamethyl-3-[2-(1-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-p-ropyl]-trisiloxane; and 1,1,1,3,5,5,5-heptamethyl-3-oxiranylmethoxy-propyl-trisiloxane.
27. The method of claim 20 wherein the fatty carboxylic acid is at least one selected from the group of naturally derived fatty carboxylic acids and synthetic fatty carboxylic acids.
28. The method of claim 20 wherein the fatty carboxylic acid is a hydrocarbon radical containing at least one carboxylic acid group and having from 2 to 34 carbon atoms.
29. The method of claim 20 wherein the fatty carboxylic acids is at least one selected from the group consisting of oleicacid, linoleic acid, linolenic acid, palmitic acid, palmitoleic acid, myristic acid, stearic acid, chaulmoogric acid, hydnocarpic acid, gorlic acid, gollic acid, ricinoleic acid, behenic acid, malvalic acid, sterculic acid, 2-hydroxy-sterculic acid and caprylic acid.
30. The method of claim 20 wherein the catalyst is at least one selected from the group consisting of tertiary amines, quaternary ammonium hydroxides, alkali hydroxides and Lewis acids.
31. The method of claim 20 wherein the catalyst is at least one selected from the group consisting of aluminum trichloride and tetraisopropyl titanate.
32. The method of claim 20 wherein amount of catalyst is from 0.001 to 0.1 weight percent of the total reactant components.
33. The method of claim 20 wherein the catalyst is from 0.001 to 0.01 weight percent of the total reactant components.
34. The method of claim 20 wherein the amount of cyclic ether silicone compound used in the reaction is from about the stoichiometric equivalent, where there is not more than 1 epoxy or oxetane group per 1 carboxylic acid group.
35. The method of claim 20 wherein the amount of cyclic ether silicone compound used in the reaction is from about 1:1 to 1:10 cyclic ether silicone/fatty acid stoichiometric ratio.
36. A product comprising the silicone compound prepared by the method of claim 20 and at least one product ingredient.
37. The product of claim 36 wherein the product ingredient is at least one selected from the group consisting of ester waxes, oils and fats of animal or vegetable origin, fatty alcohols, fatty acids, alkyl esters of fatty acids; hydrocarbon oils and waxes; water, organic solvents, surfactants, oil-soluble vitamins, water-soluble vitamins, oil-soluble drugs, water-soluble drugs, actives and pharmaceutical compounds.
38. The product of claim 36 wherein said at least one substantially pure fatty carboxylic acid used to prepare said modified silicone compound prepared by the method of claim 16 is derived from sapucainha oil.
39. A product containing the silicone compound prepared by the method of claim 20 chosen from pharmaceutical composition, medicinal and therapeutic compositions for pharmaceutical purposes and delivery systems for oil and water soluble substances.
40. A pharmaceutical composition comprising a modified silicone compound prepared according to the method of claim 20 wherein said at least one substantially pure fatty carboxylic acid is derived from sapucainha oil and at least one pharmaceutical acceptable carrier.
41. The method for producing a modified silicone compound of claim 20 wherein said substantially pure fatty carboxylic acid is derived from sapucainha oil.
42. A product comprising a modified silicone compound and at least one product ingredient, wherein the modified silicone compound is the reaction product of:
a) at least one cyclic ether silicone having the formula:
M a M A b D c D B d T e T C f Q g
wherein;
M=R 1 R 2 R 3 Si0 1/2
M A =R 4 R 5 R 6 SiO 1/2
D=R 7 R 8 SiO 1/2
D B =R 9 R 10 SiO 2/2
T=R 11 SiO 3/2
T C =R 12 SiO 3/2 ;
Q=SiO 4/2 ;
R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having from 1 to 6 carbon atoms; R 4 , R 9 , and R 12 are each independently a monovalent hydrocarbon radical containing from 3 to 25 carbon atoms and possessing at least one epoxy or oxetane group; wherein subscripts a, b, c, d, e, f, and g are zero or positive and their sum is not greater than 25, with the proviso that at least one of subscripts b, d, and f is positive; and, c+d is from 1 to 5; and
b) at least one substantially pure fatty carboxylic acid derived from sapucainha oil.
43. A modified silicone compound comprising the reaction product of:
a) at least one cyclic ether silicone having the formula:
M a M A b D c D B d T e T C f Q g
wherein;
M=R 1 R 2 R 3 Si0 1/2
M A =R 4 R 5 R 6 SiO 1/2
D=R 7 R 8 SiO 1/2
D B =R 9 R 10 SiO 2/2
T=R 11 SiO 3/2
T C =R 12 SiO 3/2 ;
Q=SiO 4/2 ;
R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having from 1 to 6 carbon atoms; R 4 , R 9 , and R 12 are each independently a monovalent hydrocarbon radical containing from 3 to 25 carbon atoms and possessing at least one epoxy or oxetane group; wherein subscripts a, b, c, d, e, f, and g are zero or positive and their sum is not greater than 25, with the proviso that at least one of subscripts b, d, and f is positive; and, c+d is from 1 to 5; and
b) at least one substantially pure fatty carboxylic acid derived from sapucainha oil.
44. A pharmaceutical composition including a modified silicone compound comprising the reaction product of:
a) at least one cyclic ether silicone having the formula:
M a M A b D c D B d T e T C f Q g
wherein;
M=R 1 R 2 R 3 Si0 1/2
M A =R 4 R 5 R 6 SiO 1/2
D=R 7 R 8 SiO 1/2
D B =R 9 R 10 SiO 2/2
T=R 11 SiO 3/2
T C =R 12 SiO 3/2 ;
Q=SiO 4/2 ;
R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having from 1 to 6 carbon atoms; R 4 , R 9 , and R 12 are each independently a monovalent hydrocarbon radical containing from 3 to 25 carbon atoms and possessing at least one epoxy or oxetane group; wherein subscripts a, b, c, d, e, f, and g are zero or positive and their sum is not greater than 25, with the proviso that at least one of subscripts b, d, and f is positive; and,
b) at least one substantially pure fatty carboxylic acid derived from sapucainha oil and at least one pharmaceutically acceptable carrier.
45. A modified silicone compound comprising the reaction product of:
a) at least one cyclic ether silicone having the formula:
M a M A b D c D B d T e T C f Q g
wherein;
M=R 1 R 2 R 3 Si0 1/2
M A =R 4 R 5 R 6 SiO 1/2
D=R 7 R 8 SiO 1/2
D B =R 9 R 10 SiO 2/2
T=R 11 SiO 3/2
T C =R 12 SiO 3/2 ;
Q=SiO 4/2 ;
R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having from 1 to 6 carbon atoms; R 4 , R 9 , and R 12 are each independently a monovalent hydrocarbon radical containing from 3 to 25 carbon atoms and possessing at least one epoxy or oxetane group; wherein subscripts a, b, c, d, e, f, and g are zero or positive and their sum is not greater than 25, with the proviso that at least one of subscripts b, d, and f is positive; and,
b) at least one substantially pure fatty carboxylic acid derived from sapucainha oil.
46. A pharmaceutical composition including a modified silicone compound prepared according to the method comprising:
i) reacting at least one cyclic ether silicone having the formula:
M a M A b D c D B d T e T C f Q g
wherein;
M=R 1 R 2 R 3 Si0 1/2
M A =R 4 R 5 R 6 SiO 1/2
D=R 7 R 8 SiO 1/2
D B =R 9 R 10 SiO 2/2
T=R 11 SiO 3/2
T C =R 12 SiO 3/2 ;
Q=SiO 4/2 ;
R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having from 1 to 6 carbon atoms; R 4 , R 9 , and R 12 are each independently a monovalent hydrocarbon radical containing from 3 to 25 carbon atoms and possessing at least one epoxy or oxetane group; wherein subscripts a, b, c, d, e, f, and g are zero or positive and their sum is not greater than 25, with the proviso that at least one of subscripts b, d, and f is positive; with at least one substantially pure fatty carboxylic acid derived from sapucainha oil and at least one pharmaceutically acceptable carrier, in the presence of at least one catalyst.
47. A method for producing a modified silicone compound comprising:
i) reacting at least one cyclic ether silicone having the formula:
M a M A b D c D B d T e T C f Q g
wherein;
M=R 1 R 2 R 3 Si0 1/2
M A =R 4 R 5 R 6 SiO 1/2
D=R 7 R 8 SiO 1/2
D B =R 9 R 10 SiO 2/2
T=R 11 SiO 3/2
T C =R 12 SiO 3/2 ;
Q=SiO 4/2 ;
R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently a monovalent hydrocarbon radical having from 1 to 6 carbon atoms; R 4 , R 9 , and R 12 are each independently a monovalent hydrocarbon radical containing from 3 to 25 carbon atoms and possessing at least one epoxy or oxetane group; wherein subscripts a, b, c, d, e, f, and g are zero or positive and their sum is not greater than 25, with the proviso that at least one of subscripts b, d, and f is positive; with at least one substantially pure fatty carboxylic acid derived from sapucainha oil, in the presence of at least one catalyst.