IP Library Granted Patent US 8,772,367
Granted Patent B2
US 8,772,367 · App. 13/052,306 · Granted Jul 8, 2014

Siloxane monomers containing hydrolysis resistance carbosiloxane linkage, process for their preparation and thin films containing the same for contact lens application

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Quick Facts
Patent No.
US 8,772,367
App. No.
13/052,306
Granted
Jul 8, 2014
Kind
B2
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 (20)

1. A silicone monomer comprising of at least one carbosiloxane linkage having the general formulae (I):

(R 1 R 2 R 3 )—Si—Y 1 —[Si(R 4 R 5 )Y 2 )] a —Si(R 6 R 7 )—Z  (I)

wherein a is 0 to about 100;

Y 1 is a substituted or unsubstituted divalent alkyl linking group of 1 to about 10 carbon atoms;

Y 2 is a substituted or unsubstituted divalent alkyl linking group of 1 to about 10 carbon atoms or a hetero atom;

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 is independently selected from the group consisting of monovalent aliphatic, cycloaliphatic or aromatic or halogenated hydrocarbon groups of 1 to about 10 carbons, —Y 2 Si(R 8 R 9 R 10 ) and A, wherein R 8 R 9 R 10 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)

R 11 —B—X  (II)

wherein R 11 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.

2. The silicone monomer of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 5 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 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.

3. 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.

4. The silicone monomer of claim 1 , wherein B is one of the following divalent moieties

—O—(C 2 H 4 O) p —(C 3 H 6 P) g —(C 4 H 8 O) 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,

5. The silicone monomer of claim 1 wherein X is acrylamide or a polymerizable moiety having the general formula (III)

wherein R 12 , R 13 , and R 14 is hydrogen or a substituted or unsubstituted saturated monovalent hydrocarbon or halogenated hydrocarbon group of 1 to about 20 carbons.

6. The silicone monomer of claim 1 , wherein the monomer is of the formula (IV):

wherein p is greater than 5.

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

Assignments (24)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
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FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
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From: KOOKMIN BANK NEW YORK
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Reel/Frame 063197/0373 →
SECURITY INTEREST Recorded Mar 30, 2023
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RELEASE OF SECURITY INTEREST Recorded May 15, 2019
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