Cross-linked aminosiloxane polymer and method of forming

Patent metadata

Field	Value
Publication number	US-9890253-B2
Application number	US-201515311664-A
Country	US
Kind code	B2
Filing date	May 20, 2015
Priority date	May 21, 2014
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

A cross-linked aminosiloxane polymer includes a first siloxane backbone, a second siloxane backbone, and at least one intramolecular structure cross-linking a silicon atom of the first siloxane backbone and a silicon atom of the second siloxane backbone. The intramolecular structure has the chemical structure: (I) In Formula (I), X is chosen from the following groups; (II); (III); or (IV). In groups (II), (III), and (IV), each R is independently a C 1 -C 10 hydrocarbon group. Each R 1 is independently a C 1 -C 10 hydrocarbon group. Each R 2 is independently a hydrogen atom, OH, a C 1 -C 12 hydrocarbon group, a phenyl group, R′(OR″) m , or R′OH. Each of R′ and R″ is independently an alkyl group and “m” is 1 to 3. Moreover, “a” is 0 or 1. The cross-linked aminosiloxane polymer can be formed by the method of this disclosure.

First claim

What is claimed is:

1. A cross-linked aminosiloxane polymer comprising a first siloxane backbone, a second siloxane backbone, and at least one intramolecular structure cross-linking a silicon atom of said first siloxane backbone and a silicon atom of said second siloxane backbone, wherein said intramolecular structure has the chemical structure:

wherein X is chosen from the following groups;

wherein each R is independently a C 1 -C 10 hydrocarbon group; each R 1 is independently a C 1 -C 10 hydrocarbon group; each R 2 is independently a hydrogen atom, OH, a C 1 -C 12 hydrocarbon group, a phenyl group, R′(OR″) m , or R′OH, where each of R′ and R″ is independently an alkyl group and “m” is 1 to 3; and “a” is 0 or 1.

2. The cross-linked aminosiloxane polymer of claim 1 , having the chemical structure:

wherein X′ is chosen from the following groups;

wherein each of R, R 1 , R 2 and “a” is as defined above; each of R 5 -R 22 is independently a hydrogen atom, a C 1 -C 12 hydrocarbon group, a C 2 -C 30 alkenyl group, a C 6 -C 12 aromatic group, R′(OR″) m , or a polyalkyleneoxy group, where each of R′, R″, and “m” is as defined above; each of “b” and “d” is independently from 1 to 100; and each of “c” and “e” is independently from 1 to 3,000.

3. The cross-linked aminosiloxane polymer of claim 1 , wherein said first siloxane backbone has the chemical structure:

wherein each of R 5 -R 13 is independently a hydrogen atom, a C 1 -C 12 hydrocarbon group, a C 2 -C 30 alkenyl group, a C 6 -C 12 aromatic group, R′(OR″) m , or a polyalkyleneoxy group, where each of R′ and R″ is independently an alkyl group and “m” is 1 to 3; “b” is from 1 to 100; “c” is from 1 to 3,000; and “L” is said intramolecular structure.

4. The cross-linked aminosiloxane polymer of claim 1 , wherein said second siloxane backbone has the chemical structure:

wherein each of R 14 -R 22 is independently a hydrogen atom, a C 1 -C 12 hydrocarbon group, a C 2 -C 30 alkenyl group, a C 6 -C 12 aromatic group, R′(OR″) m , or a polyalkyleneoxy group, where each of R′ and R″ is independently an alkyl group and “m” is 1 to 3; “d” is from 1 to 100; “e” is from 1 to 3,000; and “L” is said intramolecular structure.

5. The cross-linked aminosiloxane polymer of claim 1 , comprising the reaction product of:
a polyorganosiloxane having an amino group; and
a polyorganosiloxane that has an α,β-unsaturated carboxy acid amide group.

6. The cross-linked aminosiloxane polymer of claim 5 , wherein said polyorganosiloxane having an amino group has the chemical formula:

wherein each of R, R 1 , R 2 and “a” is as defined above; each of R 5 -R 13 is independently a hydrogen atom, a C 1 -C 12 hydrocarbon group, a C 2 -C 30 alkenyl group, a C 6 -C 12 aromatic group, R′(OR″) m , or a polyalkyleneoxy group, where each of R′, R″, and “m” is as defined above; “b” is from 1 to 100; and “c” is from 1 to 3,000.

7. The cross-linked aminosiloxane polymer of claim 5 , wherein said polyorganosiloxane that has an α,β-unsaturated carboxy acid amide group has one of the following chemical formulas:

wherein each of R, R 1 , R 2 , “a”, R 5 -R 13 , “b”, and “c” is as defined above.

8. The cross-linked aminosiloxane polymer of claim 7 , wherein said polyorganosiloxane that has an α,β-unsaturated carboxy acid amide group is the reaction product of:
a second polyorganosiloxane having an amino group; and
maleic anhydride and/or itaconic anhydride.

9. The cross-linked aminosiloxane polymer of claim 8 , wherein said maleic anhydride and/or said itaconic anhydride reacts in an amount of from about 0.01 to about 0.33 moles per 1 mole of said amino group of said second organopolysiloxane.

10. The cross-linked aminosiloxane polymer of claim 1 , wherein:
i) R is independently a C 1 -C 6 hydrocarbon group;
ii) “a” is 1; or
iii) both i) and ii).

11. A composition comprising the cross-linked aminosiloxane polymer as set forth in claim 1 , said composition chosen from cosmetic compositions, fabric treating compositions, fiber treating compositions, hair care compositions, fiber care compositions, and combinations thereof.

12. A method of forming a cross-linked aminosiloxane polymer, said method comprising the steps of:
providing a polyorganosiloxane having an amino group;
providing maleic anhydride and/or itaconic anhydride; and
combining the maleic anhydride and/or itaconic anhydride and the polyorganosiloxane having an amino group to form the cross-linked aminosiloxane polymer;
wherein the cross-linked aminosiloxane polymer comprises a first siloxane backbone, a second siloxane backbone, and at least one intramolecular structure cross-linking a silicon atom of the first siloxane backbone and a silicon atom of the second siloxane backbone, wherein the intramolecular structure has the chemical structure:

wherein X is chosen from the following groups;

wherein each R is independently a C 1 -C 10 hydrocarbon group; each R 1 is independently a C 1 -C 10 hydrocarbon group; each R 2 is independently a hydrogen atom, OH, a C 1 -C 12 hydrocarbon group, a phenyl group, R′(OR″) m , or R′OH, where each of R′ and R″ is independently an alkyl group and “m” is 1 to 3; and “a” is 0 or 1.

13. The method of claim 12 , further comprising the step of heating the polyorganosiloxane having an amino group and the maleic anhydride and/or itaconic anhydride to a temperature of from about −20° C. to about 100° C.

14. The method of claim 12 , wherein the step of providing the maleic anhydride and/or itaconic anhydride is further defined as providing about 0.01 to about 0.33 moles of the maleic anhydride and/or itaconic anhydride per 1 mole of the amino group of the polyorganosiloxane.

15. The method of claim 12 , wherein the maleic anhydride and/or itaconic anhydride reacts with the polyorganosiloxane having an amino group to form a polyorganosiloxane having an α,β-unsaturated carboxy acid amide group.

16. The cross-linked aminosiloxane polymer of claim 3 , wherein said second siloxane backbone has the chemical structure:

wherein each of R 14 -R 22 is independently a hydrogen atom, a C 1 -C 12 hydrocarbon group, a C 2 -C 30 alkenyl group, a C 6 -C 12 aromatic group, R′(OR″) m , or a polyalkyleneoxy group, where each of R′ and R″ is independently an alkyl group and “m” is 1 to 3; “d” is from 1 to 100; “e” is from 1 to 3,000; and “L” is said intramolecular structure.

Assignees

• Dow Corning

Inventors

• Feng Qian
• Fryfogle Patrick J
• Johnson Bethany K
• Li Zhi
• Nguyen Kimmai Thi
• Thomas Ryan Christopher

Classifications

• A61K8/06

  Emulsions · CPC title

• C08L2203/02

  for biomedical use · CPC title

• C08K5/1539

  Cyclic anhydrides · CPC title

• C08L2205/02

  containing two or more polymers of the same C08L -group · CPC title

• C08L83/08 Primary

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen · CPC title