Personal care compositions with acid functional silicone based structuring agents
View Patent ↗The invention is directed to personal care compositions comprising an acid functionality bearing silicone neutralized in situ with at least one aminosilane or a partially hydrolyzed aminosilane. The invention provides better stability to formulation in addition to improved delivery of hydrophilic actives from the formulation.
1. A personal care composition comprising:
(a) at least one condensation effective aminosilane or hydrolysate thereof;
(b) at least one polyorganosiloxane represented by the formula (I):
M 1 a M 2 b D 1 c D 2 d T 1 e T 2 f Q g (I)
wherein:
M 1 =R 1 R 2 R 3 SiO 1/2
M 2 =R 4 R 5 R 6 SiO 1/2
D 1 =R 7 R 8 SiO 2/2
D 2 =R 9 R 10 SiO 2/2
T 1 =R 11 SiO 3/2
T 2 =R 12 SiO 3/2
Q=SiO 4/2
wherein
R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 and R 11 are independently aliphatic, aromatic or fluoro containing monovalent hydrocarbon groups containing from 1 to about 60 carbon atoms;
R 4 , R 9 and R 12 are independently a monovalent group bearing an acid functional group selected from the group consisting of -A-COOH, -A-PO 3 H, -A-OPO 3 H and -A-SO 3 H,
wherein A is selected from the group consisting of a divalent hydrocarbon group having from about 1 to about 60 carbon atoms and a divalent arylalkylene group having the general formula —(CHR′) k C 6 H 4 (CH 2 ) h —, —CH 2 CH(R′)(CH 2 ) k C 6 H 4 —, and —CH 2 CH(R′)(CH 2 ) h C 6 H 3 R″—, wherein when A is the divalent hydrocarbon group, it is optionally substituted with heteroatoms;
wherein R′ is selected from the group consisting of hydrogen, an aliphatic having from 1 to about 60 carbon atoms, an aromatic containing monovalent hydrocarbon group having from 1 to about 60 carbon atoms and a fluoro containing monovalent hydrocarbon group having from 1 to about 60 carbon atoms, h has a value of 0 to 20, k has a value of 0 to 10;
wherein R″ is a monovalent group having from about 1 to about 20 carbon atoms, sulfur atoms, nitrogen atoms, oxygen atoms or a group containing combinations of the above atoms;
wherein the subscripts a, b, c, d, e, f and g are zero or positive and subject to the following limitations: 2≤a+b+c+d+e+f+g≤6000, and 0<b+d+f;
(c) a non-aqueous phase;
(d) an aqueous phase; and
(e) optionally, one or more surfactants, active ingredients, and pigments.
2. The personal care composition of claim 1 wherein the monovalent hydrocarbon groups R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , R 11 and R′ are independently selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert-pentyl, hexyl, heptyl, octyl, isooctyl, 2,2,4-trimethylpentyl, nonyl, decyl, cycloalkyl groups and aryl groups.
3. The personal care composition of claim 2 wherein the cycloalkyl groups are independently selected from the group consisting of cyclopentyl, cyclohexyl, cycloheptyl and methylcyclohexyl groups.
4. The personal care composition of claim 2 wherein the aryl groups are independently selected from the group consisting of phenyl, naphthyl, o-tolyl, m-tolyl, p-tolyl, xylyl, ethylphenyl and benzyl.
5. The personal care composition of claim 1 wherein at least one of R 4 , R 9 and R 12 is a monovalent group bearing an acid functional group selected from the group consisting of -A-COOH, -A-PO 3 H, -A-OPO 3 H and -A-SO 3 H.
6. The personal care composition of claim 1 wherein the at least one condensation effective aminosilane is represented by the formula (II):
wherein R 13 is a monovalent substituted hydrocarbon group of 1 to 13 carbon atoms or unsubstituted hydrocarbon group of 1 to 13 carbon atoms; R 15 is a divalent alkyl group of 1 to 20 carbon atoms or aryl group of 1 to 20 carbon atoms; R 16 is selected from hydrogen, ethyl, propyl and aminoethyl groups; R 14 is an aliphatic organic group selected from alkyl groups of 1 to 8 carbon atoms, alkylether groups of 1 to 8 carbon atoms, alkylester groups of 1 to 8 carbon atoms, alkylketone groups of 1 to 8 carbon atoms, an alkylcyano group of 7 to 15 carbon atoms or an aralkyl group of 7 to 15 carbon atoms, subscript m has a value of 0 or 1.
7. The personal care composition of claim 1 wherein the at least one condensation effective aminosilane is an alkoxysilane comprising one or more primary and/or secondary amine functional groups.
8. The personal care composition of claim 1 wherein the at least one condensation effective aminosilane is chosen from γ-aminopropyl triethoxysilane, γ-aminopropyl trimethoxysilane, γ-aminop(Currently Amended) ropylmethyl diethoxysilane, aminopropylmethyl dimethoxysilane, N-(β-aminoethyl)-γ-aminopropyl trimethoxysilane, triamino organosilanes, Bis[γ-(triethoxysilyl)propyl]amine, Bis-[γ-(trimethoxysilyl)propyl]amine, N-phenyl-γ-aminopropyl trimethoxysilane, N-ethyl-γ-aminoisobutyl trimethoxysilane and combinations thereof.
9. The personal care composition of claim 1 wherein the at least one condensation effective aminosilane is selected from the group consisting of 3-aminopropyltriethoxysilane, 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(2-aminoethylamino)propylmethyldiethoxysilane and combinations thereof.
10. The personal care composition of claim 1 wherein the at least one condensation effective aminosilane is present in the composition in an amount ranging from 0.01% to 25% by weight of the personal care composition.
11. The personal care composition of claim 1 wherein the at least one polyorganosiloxane is present in the composition in an amount ranging from 0.01% to 50% by weight of the personal care composition.
12. The personal care composition of claim 1 wherein the personal care composition further comprises solvents selected from the group consisting of ethylene glycol, ethanol, propyl alcohol, iso-propyl alcohol, propylene glycol, dipropylene glycol, tripropylene glycol, butylene glycol, iso-butylene glycol, methyl propane diol, glycerin, sorbitol, polyethylene glycol, polypropylene glycol mono alkyl ethers, polyoxyalkylene copolymers and mixtures thereof.
13. The personal care composition of claim 1 wherein the aqueous phase comprises water or an aqueous solution containing personal care ingredients.
14. The personal care composition of claim 1 wherein the personal care composition is an oil-in-water, a water-in-oil or a multiple emulsion.
15. The personal care composition of claim 1 wherein the surfactants are ionic, nonionic, polymeric or mixtures thereof.
16. The personal care composition of claim 1 wherein the active ingredients include bioactives, anti-acne agents, anti-ageing agents, anti-caries agents, anti-fungal agents, anti-microbial agents, anti-oxidants, anti-cancer, anti-viral, anti-inflammatory, anti-coagulants, hemostatic agents, exfoliants, hormones, hormone analogs, enzymes, proteins and peptides, medicinal compounds, biocides, external analgesics, oral care agents, oral care drugs, oxidizing agents, reducing agents, skin protectants, essential oils, insect repellents, UV light absorbing agents, solar filters, pigments, hydrating agents, vitamins and combinations thereof.
17. A personal care application comprising the personal care composition of claim 1 wherein the personal care application is selected from the group consisting of a skin care application, a cosmetic application, a hair care application and a keratin-shaping application.
18. A process of preparing a personal care composition comprising:
(a) at least one condensation effective aminosilane or hydrolysate thereof;
(b) at least one polyorganosiloxane represented by the formula (I):
M 1 a M 2 b D 1 c D 2 d T 1 e T 2 f Q g (I)
wherein:
M 1 =R 1 R 2 R 3 SiO 1/2
M 2 =R 4 R 5 R 6 SiO 1/2
D 1 =R 7 R 8 SiO 2/2
D 2 =R 9 R 10 SiO 2/2
T 1 =R 11 SiO 3/2
T 2 =R 12 SiO 3/2
Q=SiO 4/2
wherein
R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 and R 11 are independently aliphatic, aromatic or fluoro containing monovalent hydrocarbon groups containing from 1 to about 60 carbon atoms;
R 4 , R 9 and R 12 are independently a monovalent group bearing an acid functional group selected from the group consisting of -A-COOH, -A-PO 3 H, -A-OPO 3 H, or -A-SO 3 H,
wherein A is selected from the group consisting of a divalent hydrocarbon group having from about 1 to about 60 carbon atoms and a divalent arylalkylene group having the general formula —(CHR′) k C 6 H 4 (CH 2 ) h —, —CH 2 CH(R′)(CH 2 ) k C 6 H 4 —, and —CH 2 CH(R′)(CH 2 ) h C 6 H 3 R″—, wherein when A is the divalent hydrocarbon group, it is optionally substituted with heteroatoms;
wherein R′ is selected from the group consisting of hydrogen, an aliphatic having from 1 to about 60 carbon atoms, an aromatic containing monovalent hydrocarbon group having from 1 to about 60 carbon atoms and a fluoro containing monovalent hydrocarbon group having from 1 to about 60 carbon atoms, h has a value of 0 to 20, k has a value of 0 to 10;
wherein R″ is a monovalent group having from about 1 to about 20 carbon atoms, sulfur atoms, nitrogen atoms, oxygen atoms or a group containing combinations of the above atoms;
wherein the subscripts a, b, c, d, e, f and g are zero or positive and subject to the following limitations: 2≤a+b+c+d+e+f+g≤6000, and 0<b+d+f;
(c) a non-aqueous phase;
(d) an aqueous phase; and
(e) optionally, one or more surfactants, active ingredients, and pigments;
wherein the personal care composition is prepared by mixing the at least one polyorganosiloxane (b), the non-aqueous phase (c), the aqueous phase (d), and optionally a surfactant (e), to form an primary emulsion, followed by the addition of the at least one condensation effective aminosilane (a).
19. A process of preparing a personal care composition comprising
(a) at least one condensation effective aminosilane or hydrolysate thereof;
(b) at least one polyorganosiloxane represented by the formula (I):
M 1 a M 2 b D 1 c D 2 d T 1 e T 2 f Q g (I)
wherein:
M 1 =R 1 R 2 R 3 SiO 1/2
M 2 =R 4 R 5 R 6 SiO 1/2
D 1 =R 7 R 8 SiO 2/2
D 2 =R 9 R 10 SiO 2/2
T 1 =R 11 SiO 3/2
T 2 =R 12 SiO 3/2
Q=SiO 4/2
wherein
R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 and R 11 are independently aliphatic, aromatic or fluoro containing monovalent hydrocarbon groups containing from 1 to about 60 carbon atoms;
R 4 , R 9 and R 12 are independently a monovalent group bearing an acid functional group selected from the group consisting of -A-COOH, -A-PO 3 H, -A-OPO 3 H, or -A-SO 3 H,
wherein A is selected from the group consisting of a divalent hydrocarbon group having from about 1 to about 60 carbon atoms and a divalent arylalkylene group having the general formula —(CHR′) k C 6 H 4 (CH 2 ) h —, —CH 2 CH(R′)(CH 2 ) k C 6 H 4 —, and —CH 2 CH(R′)(CH 2 ) h C 6 H 3 R″—, wherein when A is the divalent hydrocarbon group, it is optionally substituted with heteroatoms;
wherein R′ is selected from the group consisting of hydrogen, an aliphatic having from 1 to about 60 carbon atoms, an aromatic containing monovalent hydrocarbon group having from 1 to about 60 carbon atoms and a fluoro containing monovalent hydrocarbon group having from 1 to about 60 carbon atoms, h has a value of 0 to 20, k has a value of 0 to 10;
wherein R″ is a monovalent group having from about 1 to about 20 carbon atoms, sulfur atoms, nitrogen atoms, oxygen atoms or a group containing combinations of the above atoms;
wherein the subscripts a, b, c, d, e, f and g are zero or positive and subject to the following limitations: 2≤a+b+c+d+e+f+g≤6000, and 0<b+d+f;
(c) a non-aqueous phase;
(d) an aqueous phase; and
(e) optionally, one or more surfactants, active ingredients, and pigments,
wherein the personal care composition is prepared by mixing the at least one condensation effective aminosilane (a), the aqueous phase (d), and optionally a surfactant (e), followed by the addition of the at least one polyorganosiloxane (b) and the non-aqueous phase (c).