2-aminoimidazole-functional silicone compositions and methods of making the same

Patent metadata

Field	Value
Publication number	US-9422404-B2
Application number	US-201414773762-A
Country	US
Kind code	B2
Filing date	Mar 13, 2014
Priority date	Mar 13, 2013
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

A method of making a 2-aminoimidazole-functional silicone elastomer includes forming a mixture by combining a silicone elastomer base material having vinyl functionality, a 2-aminoimidazole-functional monomer or a 2-aminoimidazole-functional oligomer, and a free-radical initiator. Optionally, one or more cross-linkers, pigments, vinyl polymer, non-functional silicone fluid, or any combination thereof may also be included in the mixture.

First claim

The invention claimed is:

1. A method of making a 2-aminoimidazole-functional silicone elastomer comprising forming a mixture by combining:
(A) a silicone elastomer base material having vinyl functionality;
(B) a 2-aminoimidazole-functional monomer or a 2-aminoimidazole-functional oligomer;
(C) a free-radical initiator; and
(D) optionally, one or more cross-linkers, pigments, vinyl polymer, non-functional silicone fluid, or any combination thereof.

2. The method of claim 1 , wherein the 2-aminoimidazole-functional monomer is

or any combination thereof.

3. The method of claim 1 , wherein the free-radical initiator is 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, dicumyl peroxide, 1,3-di(tertbutylperoxyisopropyl)-benzene, 1,4-di(tertbutylperoxyisopropyl)-benzene, 2,5-demethyl-2,5-di-tertbutylperoxy-3-hexyne, or combinations thereof.

4. The method of claim 3 , wherein the free-radical initiator is 2,5-dimethyl-2,5-di(t-butylperoxy)hexane.

5. The method of claim 1 , wherein the 2-aminoimidazole-functional monomer is 4-(dec-9-ynyl)-1H-imidazole-2-amine hydrochloride.

6. The method of claim 4 , wherein the mixture includes from 0.1 wt % to 20 wt % 2,5-dimethyl-2,5-di(t-butylperoxy)hexane.

7. The method of claim 1 , wherein the silicone elastomer base comprises dimethyl siloxane, dimethylvinylsiloxy-terminated, amorphous silica, hexamethyldisilazane, water, and dimethyl siloxane, hydroxy-terminated.

8. The method of claim 1 , wherein the mixture is heated at a temperature of from 90° C. to 200° C. for about 0.5 minutes to 210 minutes.

9. The method of claim 1 , wherein the mixture comprises about 80 wt % to about 99.5 wt % silicone elastomer base material.

10. A 2-aminoimidazole-functional silicone elastomer composition comprising:
(A) a silicone elastomer base material having vinyl functionality;
(B) a 2-aminoimidazole-functional monomer or a 2-aminoimidazole-functional oligomer; and
(C) optionally, one or more cross-linkers, pigments, vinyl polymer, non-functional silicone fluid, or any combination thereof.

11. The composition of claim 10 , wherein the composition further comprises a free-radical initiator.

12. The composition of claim 10 , wherein the 2-aminoimidazole-functional monomer is

or any combination thereof.

13. The composition of claim 11 , wherein the free-radical initiator is 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, dicumyl peroxide, 1,3-di(tertbutylperoxyisopropyl)-benzene, 1,4-di(tertbutylperoxyisopropyl)-benzene, 2,5-demethyl-2,5-di-tertbutylperoxy-3-hexyne, or combinations thereof.

14. The composition of claim 13 , wherein the free-radical initiator is 2,5-dimethyl-2,5-di(t-butylperoxy)hexane.

15. The composition of claim 14 , wherein the 2-aminoimidazole-functional monomer is 4-(dec-9-ynyl)-1H-imidazole-2-amine hydrochloride.

16. The method of claim 1 , wherein (B) is

wherein n is 2, 3, or 4, saturated or unsaturated; and R 6 is H, alkyl, alkenyl, or alkynyl; or a pharmaceutically acceptable salt or prodrug thereof.

17. The composition of claim 10 , wherein (B) is

wherein n is 2, 3, or 4, saturated or unsaturated; and R 6 is H, alkyl, alkenyl, or alkynyl; or a pharmaceutically acceptable salt or prodrug thereof.

18. The composition of claim 10 , wherein (A) comprises dimethyl siloxane, dimethylvinylsiloxy-terminated, amorphous silica, hexamethyldisilazane, water, and dimethyl siloxane, hydroxy-terminated.

19. The composition of claim 11 , wherein (A) comprises dimethyl siloxane, dimethylvinylsiloxy-terminated, amorphous silica, hexamethyldisilazane, water, and dimethyl siloxane, hydroxy-terminated.

20. The composition of claim 17 , wherein (A) comprises dimethyl siloxane, dimethylvinylsiloxy-terminated, amorphous silica, hexamethyldisilazane, water, and dimethyl siloxane, hydroxy-terminated.

Assignees

• Dow Corning

Inventors

• Curtis James
• Schulz William J

Classifications

• C09D5/1675 Primary

  Polyorganosiloxane-containing compositions · CPC title

• C08K5/0025

  Crosslinking or vulcanising agents; including accelerators · CPC title

• C09D183/04

  Polysiloxanes · CPC title

• C08K5/3445

  Five-membered rings · CPC title

• C08G77/26 Primary

  nitrogen-containing groups · CPC title