# US 8,772,367 B2 · Siloxane monomers containing hydrolysis resistance carbosiloxane linkage, process for their preparation and thin films containing the same for contact lens application

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 8,772,367 B2
- Document ID: US8772367B2
- Status: Granted
- Kind: B2
- Application number: 13/052,306
- Filed: 2011-03-21
- Published: 2012-09-27
- Granted: 2014-07-08
- Earliest claimed: 2011-03-21
- Assignees: Momentive Performance Materials Inc.
- Applicants: Anubhav Saxena; Umapathy Senthilkumar; Kenrick M. Lewis
- Inventors: Anubhav Saxena; Umapathy Senthilkumar; Kenrick M. Lewis
- Web page: https://patentgrep.com/patent/US8772367B2

## CPC

- C08L 43/04: Homopolymers or copolymers of monomers containing silicon
- C07F 7/0838: {Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21)}
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

There is provided new mono-(meth)acrylate functionalized silicone monomers containing carbosiloxane linkage for improved hydrolysis resistance, useful in making water absorbing silicone-hydrogel films for contact lens applications. This invention also provides homo-polymers and copolymers made from the mono-(meth)acrylate functionalized hydrophilic silicone monomers described herein. Also provided is a process for producing the monomers and polymers described herein and contact lenses produced from the same.

## Claims

### Claim 1

A silicone monomer comprising of at least one carbosiloxane linkage having the general formulae (I):
(R1R2R3)—Si—Y1—[Si(R4R5)Y2)]a—Si(R6R7)—Z (I)
wherein a is 0 to about 100;
Y1 is a substituted or unsubstituted divalent alkyl linking group of 1 to about 10 carbon atoms;
Y2 is a substituted or unsubstituted divalent alkyl linking group of 1 to about 10 carbon atoms or a hetero atom;
R1, R2, R3, R4, R5, R6, and R7 is independently selected from the group consisting of monovalent aliphatic, cycloaliphatic or aromatic or halogenated hydrocarbon groups of 1 to about 10 carbons, —Y2Si(R8R9R10) and A, wherein R8R9R10 is independently selected from the group consisting of monovalent aliphatic, cycloaliphatic and aromatic hydrocarbon groups of 1 to about 10 carbons; A is a monovalent hydrophilic or hydrophobic moiety selected from the group consisting of substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons and substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons containing hetero atoms;
Z has the following general formulae (II)
R11—B—X (II)
wherein R11 is a linear or branched, divalent alkyl linking group having 0 to about 20 carbon atoms, B is a divalent hydrophilic or hydrophobic moiety selected from the group consisting of substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons and substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons containing hetero atoms, wherein B comprises a functionality chosen from an alcohol chosen from a hydroxycyclohexanyl, an ether, an ester, an amide, an amine, an acid and its salts, a cyano, a thio, a urethane, a urea, a carbonate, a carbamate, a sulfonate, a sulphonomide, a phosphate, or combinations thereof, and X is acrylamide or a polymerizable group selected from the group consisting of substituted or unsubstituted unsaturated aliphatic hydrocarbons, substituted or unsubstituted aromatic hydrocarbons, acrylates, and methacrylates.

### Claim 2 (depends on 1)

The silicone monomer of claim 1, wherein R1, R2, R3, R4, R5, R6, R7, R5, R9, R10, R11, R12, R13 and R14 independently comprises a saturated monovalent hydrocarbon group of 1 to about 9 carbon atoms, a fluorinated hydrocarbon, a aralkyl or arylalkyl group, or a siloxanyl group.

### Claim 3 (depends on 1)

The silicone monomer of claim 1, wherein A and B comprise at least one functional group consisting of alkyl, alcohol, ether, ester, amide, amine, acid and its salts, cyano, thio, urethane, urea, carbonate, carbamate, sulfonate, sulphonamide, and phosphate.

### Claim 4 (depends on 1)

The silicone monomer of claim 1, wherein B is one of the following divalent moieties
—O—(C2H4O)p—(C3H6P)g—(C4H8O)r—
Polyether
wherein p and q are independently 0 to about 100; r is 0 to about 50 and (p+q+r) is greater than 0,

### Claim 5 (depends on 1)

The silicone monomer of claim 1 wherein X is acrylamide or a polymerizable moiety having the general formula (III)
wherein R12, R13, and R14 is hydrogen or a substituted or unsubstituted saturated monovalent hydrocarbon or halogenated hydrocarbon group of 1 to about 20 carbons.

### Claim 6 (depends on 1)

The silicone monomer of claim 1, wherein the monomer is of the formula (IV):
wherein p is greater than 5.

### Claim 7 (depends on 1)

The silicone monomer of claim 1, wherein the monomer is of the formula (V):