# US 10,870,731 B2 · Method for end-capping a polysiloxane prepolymer

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

- Number: US 10,870,731 B2
- Document ID: US10870731B2
- Status: Granted
- Kind: B2
- Application number: 16/246,715
- Filed: 2019-01-14
- Published: 2019-08-01
- Granted: 2020-12-22
- Earliest claimed: 2018-01-26
- Assignees: Bausch & Lomb Incorporated
- Applicants: Bausch & Lomb Incorporated
- Inventors: Ivan M. Nuñez; Katie L. Poetz; Andrew J. Hoteling; Joseph W. Hoff; Lynn Coullard; Analuz Mark; Keyla M. Cubi; Joseph A. McGee
- Web page: https://patentgrep.com/patent/US10870731B2

## CPC

- C08G 77/38: Polysiloxanes modified by chemical after-treatment
- A61L 27/18: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C08G 77/20: containing silicon bound to unsaturated aliphatic groups
- C08G 77/26: nitrogen-containing groups
- C08G 77/388: containing nitrogen
- C08L 83/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- G02B 1/043: {Contact lenses}
- A61F 2/16: Intraocular lenses
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- A61F: FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS (dental prosthetics A61C)

## Abstract

A method is disclosed which involves the steps of (a) reacting a polysiloxane prepolymer having reactive functional end groups with a non-free radical polymerizable reactive end-capping agent; and (b) reacting the reaction product of step (a) with a free radical polymerizable reactive end-capping agent.

## Claims

### Claim 1

A method comprising the steps of:
(a) reacting a polysiloxane prepolymer having reactive functional end groups with a non-free radical polymerizable reactive end-capping agent, wherein the non-free radical polymerizable reactive end-capping agent is one of a carbonyl-containing non-free radical polymerizable reactive end-capping agent of the general formula:
wherein R8 is a non-reactive moiety and C(O)X is a non-free radical polymerizable reactive group, or a chloroformate of the general formula:
wherein R8 has the aforestated meaning; and
(b) reacting the reaction product of step (a) with a free-radical polymerizable reactive end-capping agent.

### Claim 2 (depends on 1)

The method of claim 1, wherein the polysiloxane prepolymer is of formula I:
wherein each R is an independently reactive functional end group, R1 to R6 are independently straight or branched, substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C4-C30 cycloalkylalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C7-C30 arylalkyl group, and L is independently a linking group.

### Claim 3 (depends on 2)

The method of claim 2, wherein the reactive functional end group includes the same or different reactive functional end group selected from the group consisting of a hydroxyl-containing reactive functional end group and an amine-containing reactive functional end group.

### Claim 4 (depends on 1)

The method of claim 1, wherein the reactive functional end group is —OH.

### Claim 5 (depends on 1)

The method of claim 1, wherein the reactive functional end group is an amine-containing reactive functional end group of the general formula —NHR7 wherein R7 is independently hydrogen, an alkyl group, an aryl group, and a cycloalkyl group.

### Claim 6 (depends on 1)

The method of claim 1, wherein the L linking group is independently a straight or branched alkyl group, cycloalkyl group, an aryl group, an ether or polyether group, and an ester group.

### Claim 7 (depends on 1)

The method of Claim 1, wherein R8 is selected from the group consisting of C1 to C18 alkyl groups, C3 to C18 cycloalkyl groups and C6 to C18 aryl groups and X is selected from the group consisting of —OH, halogen and —OR9 wherein R9 is a substituted or unsubstituted heteroaryl or —C(O)R8 wherein le has the aforestated meanings.

### Claim 8 (depends on 1)

The method of claim 1, wherein the non-free radical polymerizable reactive end-capping agent is reacted with the polysiloxane prepolymer in an amount ranging from about 3 to about 15 mole % of non-free radical polymerizable reactive end-capping agent per mole of end groups in the polymer.

### Claim 9 (depends on 1)

The method of claim 1, wherein the non-free radical polymerizable reactive end-capping agent is reacted with the polysiloxane prepolymer in an amount ranging from about 1 to about 30 mole % of non-free radical polymerizable reactive end-capping agent per mole of end groups in the polymer.

### Claim 10 (depends on 1)

The method of claim 1, wherein the non-free radical polymerizable reactive end-capping agent is reacted with the polysiloxane prepolymer at a temperature ranging from about 0° C. to about 40° C.

### Claim 11 (depends on 1)

The method of claim 1, wherein the free radical polymerizable reactive end-capping agent is a free radical polymerizable reactive end-capping agent having at least one ethylenically unsaturated reactive end group.

### Claim 12 (depends on 1)

The method of claim 1, wherein the free radical polymerizable reactive end-capping agent is selected from the group consisting of a (meth)acrylate-containing free radical polymerizable reactive end-capping agent, a vinyl-containing free radical polymerizable reactive end-capping agent, an unsaturated acidic-containing free radical polymerizable reactive end-capping agent and a styryl-containing free radical polymerizable reactive end-capping agent.

### Claim 13 (depends on 12)

The method of claim 12, wherein the free radical polymerizable reactive end-capping agent is a (meth)acrylate-containing free radical polymerizable reactive end-capping agent selected from the group consisting of a symmetrical (meth)acrylate-containing acid anhydride free radical polymerizable reactive end-capping agent, a (meth)acrylate-containing acid chloride free radical polymerizable reactive end-capping agent, a (meth)acrylate-containing carboxylic acid free radical polymerizable reactive end-capping agent, a (meth)acrylate-containing carbonyl-containing free radical polymerizable reactive end-capping agent, and a (meth)acrylate-containing isocyanate- containing free radical polymerizable reactive end-capping agent.

### Claim 14 (depends on 12)

The method of claim 12, wherein the free radical polymerizable reactive end-capping agent is a vinyl-containing free radical polymerizable reactive end-capping agent selected from the group consisting of a vinyl isocyanate free radical polymerizable reactive end-capping agent, and a vinyl chloroformate free radical polymerizable reactive end-capping agent.

### Claim 15 (depends on 12)

The method of claim 12, wherein the free radical polymerizable reactive end-capping agent is an unsaturated acidic-containing free radical polymerizable reactive end-capping agent which is maleic anhydride.

### Claim 16 (depends on 1)

The method of claim 1, wherein the free radical polymerizable reactive end-capping agent is reacted with the product of step (a) in an excess amount.

### Claim 17 (depends on 1)

The method of claim 1, wherein the free radical polymerizable reactive end- capping agent is reacted with the product of step (a) at a temperature ranging from about 0° C. to about 40° C.

### Claim 18 (depends on 1)

The method of claim 1, wherein the product of step (b) is further reacted with one or more biomedical-device forming monomers to obtain a biomedical device.

### Claim 19 (depends on 18)

The method of claim 18, wherein the biomedical device is an ophthalmic lens.

### Claim 20 (depends on 18)

The method of claim 18, wherein the biomedical device is a contact lens.

### Claim 21 (depends on 18)

The method of claim 18, wherein the biomedical device is an intraocular lens.

### Claim 22 (depends on 1)

The method of claim 1, wherein the carbonyl-containing non-free radical polymerizable reactive end-capping agent is represented by a structure of the general formula:
wherein R8 has the aforestated meaning.

### Claim 23 (depends on 1)

The method of claim 1, wherein the reaction of the non-free radical polymerizable reactive end-capping agent with the polysiloxane prepolymer is carried out in the presence of a solvent.