Compositions comprising siloxane compounds and methods for using the same

Patent metadata

Field	Value
Publication number	US-10246558-B2
Application number	US-201715596681-A
Country	US
Kind code	B2
Filing date	May 16, 2017
Priority date	May 20, 2016
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

Abstract

A composition comprises a first siloxane compound comprising at least one cyclic siloxane moiety and a first salt, the first salt comprising a conjugate base of a volatile organic acid. A method for producing a cross-linked siloxane network comprises the steps of providing a first siloxane compound comprising at least one cyclic siloxane moiety, providing a first salt comprising a conjugate base of a volatile organic acid, combining the first siloxane compound and the first salt to produce a reaction mixture, heating the reaction mixture to a temperature sufficient for the first salt to open the ring of the cyclic siloxane moiety, and maintaining the reaction mixture at an elevated temperature so that at least a portion of the opened cyclic siloxane moieties react with each other to produce a cross-linked siloxane network.

First claim

What is claimed is:

1. A composition comprising:
(a) a first siloxane compound of Formula (X)

wherein the variable n is selected from the group consisting of integers equal to or greater than 1; R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 are independently selected from the group consisting of alkyl groups, substituted alkyl groups, cycloalkyl groups, substituted cycloalkyl groups, alkenyl groups, substituted alkenyl groups, cycloalkenyl groups, substituted cycloalkenyl groups, heterocyclyl groups, substituted heterocyclyl groups, aryl groups, substituted aryl groups, heteroaryl groups, substituted heteroaryl groups, and siloxy groups; at least one of R 7 and R 8 is different from each of R 2 , R 3 , R 4 , R 5 , and R 6 , and at least one of R 16 and R 17 is different from each of R 13 , R 14 , R 15 , R 18 , and R 19 ; and
(b) a first salt, the first salt comprising a conjugate base of a volatile organic acid, wherein the first salt is selected from the group consisting of tetramethylammonium formate, tetramethylammonium acetate, tetramethylammonium malonate, tetramethylammonium succinate, tetrabutylammonium formate, tetrabutylammonium acetate, tetrabutylammonium malonate, tetrabutylammonium succinate, tetrabutylphosphonium formate, tetrabutylphosphonium acetate, tetrabutylphosphonium malonate, tetrabutylphosphonium succinate, tetrabutylphosphonium bicarbonate, and mixtures thereof.

2. The composition of claim 1 , wherein the first salt is selected from the group consisting of tetrabutylphosphonium formate, tetrabutylphosphonium acetate, tetrabutylphosphonium malonate, tetrabutylphosphonium succinate, tetrabutylphosphonium bicarbonate, and mixtures thereof.

3. The composition of claim 1 , wherein the composition further comprises a second salt, and the second salt is a hydroxide salt.

4. The composition of claim 3 , wherein the second salt is selected from the group consisting of lithium hydroxide, sodium hydroxide, potassium hydroxide, ammonium hydroxides, phosphonium hydroxides, and mixtures thereof.

5. The composition of claim 4 , wherein the second salt is selected from the group consisting of ammonium hydroxides, phosphonium hydroxides, and mixtures thereof.

6. The composition of claim 5 , wherein the second salt is selected from the group consisting of tetramethylammonium hydroxide, tetrabutylammonium hydroxide, tetrabutylphosphonium hydroxide, and mixtures thereof.

7. The composition of claim 1 , wherein the composition further comprises a second siloxane compound, the second siloxane compound comprising at least one cyclic siloxane moiety.

8. A method for producing a cross-linked siloxane network, the method comprising the steps of:
(a) providing a first siloxane compound of Formula (X)

wherein the variable n is selected from the group consisting of integers equal to or greater than 1; R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 are independently selected from the group consisting of alkyl groups, substituted alkyl groups, cycloalkyl groups, substituted cycloalkyl groups, alkenyl groups, substituted alkenyl groups, cycloalkenyl groups, substituted cycloalkenyl groups, heterocyclyl groups, substituted heterocyclyl groups, aryl groups, substituted aryl groups, heteroaryl groups, substituted heteroaryl groups, and siloxy groups; at least one of R 7 and R 8 is different from each of R 2 , R 3 , R 4 , R 5 , and R 6 , and at least one of R 16 and R 17 is different from each of R 13 , R 14 , R 15 , R 18 , and R 19 ;
(b) providing a first salt, the first salt comprising a conjugate base of a volatile organic acid, wherein the first salt is selected from the group consisting of tetramethylammonium formate, tetramethylammonium acetate, tetramethylammonium malonate, tetramethylammonium succinate, tetrabutylammonium formate, tetrabutylammonium acetate, tetrabutylammonium malonate, tetrabutylammonium succinate, tetrabutylphosphonium formate, tetrabutylphosphonium acetate, tetrabutylphosphonium malonate, tetrabutylphosphonium succinate, tetrabutylphosphonium bicarbonate, and mixtures thereof;
(c) combining the first siloxane compound and the first salt to produce a reaction mixture;
(d) heating the reaction mixture to a temperature sufficient for the first salt to open the ring of the cyclic siloxane moiety; and
(e) maintaining the reaction mixture at an elevated temperature so that at least a portion of the opened cyclic siloxane moieties react with each other to produce a cross-linked siloxane network.

9. The method of claim 8 , wherein the first salt is selected from the group consisting of tetrabutylphosphonium formate, tetrabutylphosphonium acetate, tetrabutylphosphonium malonate, tetrabutylphosphonium succinate, tetrabutylphosphonium bicarbonate, and mixtures thereof.

10. The method of claim 8 , wherein the method further comprises the step of providing a second salt, the second salt is a hydroxide salt, and the second salt is combined with the first siloxane compound and the first salt to produce the reaction medium.

11. The method of claim 10 , wherein the second salt is selected from the group consisting of lithium hydroxide, sodium hydroxide, potassium hydroxide, ammonium hydroxides, phosphonium hydroxides, and mixtures thereof.

12. The method of claim 11 , wherein the second salt is selected from the group consisting of ammonium hydroxides, phosphonium hydroxides, and mixtures thereof.

13. The method of claim 12 , wherein the second salt is selected from the group consisting of tetramethylammonium hydroxide, tetrabutylammonium hydroxide, tetrabutylphosphonium hydroxide, and mixtures thereof.

14. The method of claim 8 , wherein the method further comprises the step of providing a second siloxane compound, the second siloxane compound comprising at least one cyclic siloxane moiety, and wherein the second siloxane compound is combined with the first siloxane compound and the first salt to produce the reaction mixture.

15. The composition of claim 1 , wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 13 , R 14 , R 15 , R 18 , and R 19 are independently selected from the group consisting of alkyl groups, substituted alkyl groups, cycloalkyl groups, substituted cycloalkyl groups, alkenyl groups, substituted alkenyl groups, cycloalkenyl groups, substituted cycloalkenyl groups, heterocyclyl groups, substituted heterocyclyl groups, and siloxy groups.

16. The composition of claim 15 , wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 13 , R 14 , R 15 , R 18 , and R 19 are independently selected from the group consisting of alkyl groups.

17. The composition of claim 16 , wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 13 , R 14 , R 15 , R 18 , and R 19 are each methyl.

18. The composition of claim 1 , wherein R 7 , R 8 , R 11 , R 12 , R 16 , and R 17 are independently selected from the group consisting of haloalkyl groups, aralkyl groups, aryl groups, substituted aryl groups, heteroaryl groups, and substituted heteroaryl groups.

19. The composition of claim 17 , wherein R 7 , R 8 , R 11 , R 12 , R 16 , and R 17 are independently selected from the group consisting of aryl groups.

20. The composition of claim 18 , wherein R 7 , R 6 , R 11 , R 12 , R 16 , and R 17 are each phenyl.

21.

Assignees

• Milliken & Co

Inventors

• Srivastava Sudhanshu
• Stankovich Sasha
• Wilson Michael E
• Hanssen Robbie W J
• Torres Eduardo
• Thivierge Cliferson
• Stapleton Russell A
• Monroe Eric B

Classifications

• C08G77/08 Primary

  characterised by the catalysts used · CPC title

• C08L83/04

  Polysiloxanes · CPC title

• C08G77/04

  Polysiloxanes · CPC title

• C08L83/00

  Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers · CPC title

• C08K5/098

  Metal salts of carboxylic acids · CPC title