# US 10,246,558 B2 · Compositions comprising siloxane compounds and methods for using the same

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- Number: US 10,246,558 B2
- Document ID: US10246558B2
- Status: Granted
- Kind: B2
- Application number: 15/596,681
- Filed: 2017-05-16
- Published: 2017-11-23
- Granted: 2019-04-02
- Earliest claimed: 2016-05-20
- Assignees: Milliken & Company
- Applicants: Milliken & Company
- Inventors: Sudhanshu Srivastava; Sasha Stankovich; Michael E. Wilson; Robbie W. J. Hanssen; Eduardo Torres; Cliferson Thivierge; Russell A. Stapleton; Eric B. Monroe
- Web page: https://patentgrep.com/patent/US10246558B2

## CPC

- C08G 77/06: Preparatory processes
- C08G 77/04: Polysiloxanes
- C08G 77/08: characterised by the catalysts used
- C08K 5/098: Metal salts of carboxylic acids
- C08K 5/19: Quaternary ammonium compounds
- C08L 83/00: 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
- C08L 83/04: Polysiloxanes
- C08G 77/045: {containing less than 25 silicon atoms}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## 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.

## Claims

### Claim 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; R2, R3, R4, R5, R6, R7, R8, R11, R12, R13, R14, R15, R16, R17, R18, and R19 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 R7 and R8 is different from each of R2, R3, R4, R5, and R6, and at least one of R16 and R17 is different from each of R13, R14, R15, R18, and R19; 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.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 3)

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.

### Claim 5 (depends on 4)

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

### Claim 6 (depends on 5)

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.

### Claim 7 (depends on 1)

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.

### Claim 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; R2, R3, R4, R5, R6, R7, R8, R11, R12, R13, R14, R15, R16, R17, R18, and R19 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 R7 and R8 is different from each of R2, R3, R4, R5, and R6, and at least one of R16 and R17 is different from each of R13, R14, R15, R18, and R19;
(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.

### Claim 9 (depends on 8)

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.

### Claim 10 (depends on 8)

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.

### Claim 11 (depends on 10)

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.

### Claim 12 (depends on 11)

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

### Claim 13 (depends on 12)

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.

### Claim 14 (depends on 8)

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.

### Claim 15 (depends on 1)

The composition of claim 1, wherein R2, R3, R4, R5, R6, R13, R14, R15, R18, and R19 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.

### Claim 16 (depends on 15)

The composition of claim 15, wherein R2, R3, R4, R5, R6, R13, R14, R15, R18, and R19 are independently selected from the group consisting of alkyl groups.

### Claim 17 (depends on 16)

The composition of claim 16, wherein R2, R3, R4, R5, R6, R13, R14, R15, R18, and R19 are each methyl.

### Claim 18 (depends on 1)

The composition of claim 1, wherein R7, R8, R11, R12, R16, and R17 are independently selected from the group consisting of haloalkyl groups, aralkyl groups, aryl groups, substituted aryl groups, heteroaryl groups, and substituted heteroaryl groups.

### Claim 19 (depends on 17)

The composition of claim 17, wherein R7, R8, R11, R12, R16, and R17 are independently selected from the group consisting of aryl groups.

### Claim 20 (depends on 18)

The composition of claim 18, wherein R7, R6, R11, R12, R16, and R17 are each phenyl.

### Claim 21 (depends on 8)

The method of claim 8, wherein R2, R3, R4, R5, R6, R13, R14, R15, R18, and R19 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.

### Claim 22 (depends on 20)

The method of claim 20, wherein R2, R3, R4, R5, R6, R13, R14, R15, R18, and R19 are independently selected from the group consisting of alkyl groups.

### Claim 23 (depends on 21)

The method of claim 21, wherein R2, R3, R4, R5, R6, R13, R14, R15, R18, and R19 are each methyl.

### Claim 24 (depends on 8)

The method of claim 8, wherein R7, R8, R11, R12, R16, and R17 are independently selected from the group consisting of haloalkyl groups, aralkyl groups, aryl groups, substituted aryl groups, heteroaryl groups, and substituted heteroaryl groups.

### Claim 25 (depends on 23)

The method of claim 23, wherein R7, R8, R11, R12, R16, and R17 are independently selected from the group consisting of aryl groups.

### Claim 26 (depends on 24)

The method of claim 24, wherein R7, R8, R11, R12, R16, and R17 are each phenyl.