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

• US 8,772,367 B2
• Filed: 03/21/2011
• Issued: 07/08/2014
• Est. Priority Date: 03/21/2011
• Status: Active Grant

• Current Assignee: Momentive Performance Materials Incorporated (Momentive Performance Materials Holdings LLC)
• Original Assignee: Momentive Performance Materials Incorporated (Momentive Performance Materials Holdings LLC)
• Inventors: Saxena, Anubhav, Senthilkumar, Umapathy, Lewis, Kenrick M.
• Primary Examiner(s): PEPITONE, MICHAEL F
• Application Number:
  US13/052,306
• Publication Number:
  US 20120245249A1
• Time in Patent Office: 1,205 Days
• Field of Search: 523/107, 556/400, 556/431, 556/434, 556/436, 556/437, 556/438, 556/439, 556/465, 556/482
• US Class Current: 523/107
• CPC Class Codes: 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
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon

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

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.

2. 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.

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—

(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,

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

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

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