Aminosiloxane ester copolymer and methods for the preparation and use of the copolymer
An aminosiloxane ester copolymer, an emulsion containing the copolymer, and processes for making the copolymer and the emulsion are provided. The copolymer and the emulsion may be formulated into hair care compositions, such as conditioners and styling products.
1 . An aminosiloxane ester copolymer comprises formula:
where each R 1 is an independently selected monovalent hydrocarbon group of 1 to 12 carbon atoms, each R E is independently selected from the group consisting of hydroxyl and an amino-functional group of formula H 2 N—R A —, each R A is an independently selected divalent hydrocarbon group of 1 to 12 carbon atoms, each R 2 is independently selected from the group consisting of hydrogen and methyl, each R D is an independently selected divalent hydrocarbon group of 2 to 20 carbon atoms, each subscript a independently has a value such that 0≤a<220, and subscript b has a value such that 1≤b≤100.
2 . The copolymer of claim 1 , where one or more of conditions i) to vii) are satisfied, where condition i) is that subscript a is 2 to 200; condition ii) is that subscript b is 2 to 20; condition iii) is that each R D has 3 to 12 carbon atoms; condition iv) is that each R 2 is hydrogen; condition v) is that each R 1 is an alkyl group of 1 to 6 carbon atoms; condition vi) is that each R A is an alkyl group of 1 to 6 carbon atoms; and condition vii) is that the copolymer has a number average molecular weight of >1,000 g/mole to 250,000 g/mol measured by gel permeation chromatography.
3 . The copolymer of claim 1 , where subscript a has value of 16 to 84.
4 . An emulsion comprising:
(I) a liquid continuous phase comprising water, and
(II) a discontinuous phase dispersed in the liquid continuous phase, where the discontinuous phase comprises the aminosiloxane ester copolymer of claim 1 .
5 . The emulsion of claim 4 , where the emulsion further comprises an additional starting material selected from the group consisting of (H) a surfactant, (I) an acid compound, (J) an acid anhydride, (K) a thickener, (L) a stabilizer, and a combination of two or more of (H), (I), (J), (K), and (L).
6 . A process for preparing the copolymer of claim 1 , where each R E is the amino-functional group, and where the process comprises:
1) Combining starting materials comprising
(A) a terminal primary amino-functional polyorganosiloxane of formula
where each R 1 is an independently selected monovalent hydrocarbon group of 1 to 12 carbon atoms, each R A is an independently divalent hydrocarbon group of 1 to 12 carbon atoms, subscript a has a value such that 0≤a<220; and
(B) a bis-acryloyloxy-alkane of formula
where R D is a divalent hydrocarbon group of 2 to 20 carbon atoms;
where starting material (A) and starting material (B) are present in amounts such that a molar ratio of (A):(B) ranges from 2:1 to 1:1.1.
7 . The process of claim 6 , where (B) the bis-acryloyloxy-alkane is selected from the group consisting of 1,3-butanediol diacrylate; 1,4-butanediol diacrylate; 1,6-hexanediol diacrylate; 1,9-nonanediol diacrylate; 1,10-decanediol diacrylate; and a combination of two or more of 1,3-butanediol diacrylate; 1,4-butanediol diacrylate; 1,6-hexanediol diacrylate; 1,9-nonanediol diacrylate; and 1,10-decanediol diacrylate.
8 . The process of claim 6 , further comprising adding, during step 1), an additional starting material selected from the group consisting of: (C) a catalyst, (D) a solvent, (E) an acrylate polymerization inhibitor, and a combination of two or more of (C), (D), and (E).
9 . The process of claim 6 , where one or both of conditions (a) and (b) is satisfied, where condition (a) is that combining in step 1) comprises mixing and heating the starting materials at a temperature of 0° C. to 180° C.; and condition (b) is that combining in step 1) is performed for 1 to 48 hours.
10 . The process of claim 6 , further comprising: 2) recovering the copolymer during and/or after step 1).
11 . A process for preparing the copolymer of claim 1 , wherein the process comprises:
1) Combining starting materials comprising:
(B) a bis-acryloyloxy-alkane of formula
where R D is a divalent hydrocarbon group of 2 to 20 carbon atoms;
(F) a bis-silanol-terminated polydiorganosiloxane of formula:
where R 1 is an independently selected monovalent hydrocarbon group of 1 to 12 carbon atoms, and subscript a independently has a value such that 0≤a<220;
(G) a cyclic siloxazane of formula
where subscript c is 0 or 1, each R 8 is an independently selected monovalent hydrocarbon group of 1 to 18 carbon atoms, each R 9 is independently selected from the group consisting of hydrogen and an alkyl group of 1 to 15 carbon atoms.
12 . The process of claim 11 , where less than 2 molar equivalents of (G) the cyclic siloxazane, per mole of (F) the bis-silanol-terminated polydiorganosiloxane are used in the process.
13 . The process of claim 11 , where 2 or more molar equivalents of (G) the cyclic siloxazane, per mole of (F) the bis-silanol-terminated polydiorganosiloxane are used in the process.
14 . The process of claim 11 , where (B) the bis-acryloyloxy-alkane is selected from the group consisting of 1,3-butanediol diacrylate; 1,4-butanediol diacrylate; 1,6-hexanediol diacrylate; 1,9-nonanediol diacrylate; 1,10-decanediol diacrylate; and a combination of two or more of 1,3-butanediol diacrylate; 1,4-butanediol diacrylate; 1,6-hexanediol diacrylate; 1,9-nonanediol diacrylate; and 1,10-decanediol diacrylate.
15 . The process of claim 11 , further comprising adding, during step 1), an additional starting material selected from the group consisting of: (C) a catalyst, (D) a solvent, (E) an acrylate polymerization inhibitor, and a combination of two or more of (C), (D), and (E).
16 . The process of claim 11 , where one or both of conditions (a) and (b) is satisfied, where condition (a) is that combining in step 1) comprises mixing and heating the starting materials at a temperature of 0° C. to 180° C.; and condition (b) is that combining in step 1) is performed for 1 to 48 hours.
17 . The process of claim 11 , further comprising: 2) recovering the copolymer during and/or after step 1).
18 . A method for preparing an emulsion, the method comprising: mixing under shear starting materials comprising the copolymer of claim 1 , water, and optionally one or more starting material selected from the group consisting of (H) a surfactant, (I) an acid compound, (J) an acid anhydride, (K) a thickener, and (L) a stabilizer.
19 . A method comprising: applying a hair care composition to hair, wherein the hair care composition comprises the copolymer of claim 1 .
20 . The method of claim 19 , where the hair care composition is a conditioner or a styling product.