IP Library Granted Patent US 9,890,253
Granted Patent B2
US 9,890,253 · App. 15/311,664 · Granted Feb 13, 2018

Cross-linked aminosiloxane polymer and method of forming

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,890,253
App. No.
15/311,664
Granted
Feb 13, 2018
Kind
B2
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.

Claims (45)

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.

17. The cross-linked aminosiloxane polymer of claim 6 , 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.

18. The cross-linked aminosiloxane polymer of claim 17 , 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.

19. The cross-linked aminosiloxane polymer of claim 18 , 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.

20. The method of claim 13 , 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.

Assignments (2)
CHANGE OF NAME Recorded Feb 27, 2018
From: DOW CORNING CORPORATION
To: DOW SILICONES CORPORATION
Reel/Frame 045460/0278 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 21, 2016
From: FENG, QIAN JANE; FRYFOGLE, PATRICK J.; JOHNSON, BETHANY K.; LI, ZHI; NGUYEN, KIMMAI THI; THOMAS, RYAN CHRISTOPHER
To: DOW CORNING CORPORATION
Reel/Frame 040393/0450 →