UV curable crosslinking agents useful in copolymerization

• US 5,512,205 A
• Filed: 05/09/1994
• Issued: 04/30/1996
• Est. Priority Date: 11/05/1991
• Status: Expired due to Term

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Lai, Yu-Chin
• Primary Examiner(s): Cain, Edward J.
• Application Number:
  US08/242,652
• Time in Patent Office: 722 Days
• Field of Search: 252/182.14, 252/182.15, 252/182.17, 252/182.18, 252/182.23, 252/182.28
• US Class Current: 252/182.14
• CPC Class Codes: C07C 233/20 having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
• CPC Class Codes: C07C 271/12 to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
• CPC Class Codes: C07C 271/44 to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
• CPC Class Codes: C07C 275/50 Y being a hydrogen or an acyclic carbon atom
• CPC Class Codes: C07C 327/30 having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
• CPC Class Codes: C07C 69/96 Esters of carbonic or haloformic acids
• CPC Class Codes: C07F 7/0803 Compounds with Si-C or Si-Si linkages
• 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: C08F 246/00 Copolymers in which the nature of only the monomers in minority is defined
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A novel class of compounds are disclosed which may be used as novel crosslinking agents for acrylic-containing, vinyl-containing and/or styrene-containing hydrophilic monomers to prepare novel UV-curable hydrophilic copolymers suitable for use as biomedical articles, especially contact lenses.

Claims

1. A composition having at least two different types of ethylenically polymerizable groups and having the schematic representation:

##STR15## wherein V denotes a vinyl-containing group having the formula;

##STR16## A'"'"' denotes an acrylic-containing group having the formula;

##STR17## S denotes a styrene-containing group having the formula;

##STR18## wherein R_1'"'"' is an alkyl radical, polyalkylene oxide, poly(perfluoro) alkylene oxide, dialkyl-capped polydimethylsiloxane, dialkyl-capped polydimethylsiloxane modified with fluoroalkyl or fluoroether groups;

R_2'"'"' -R_10'"'"' are independently H, or alkyl of 1 to 5 carbon atoms;

Q is an organic group containing aromatic moieties having 6-30 carbon atoms;

X, Y, and Z are independently O, NH or S;

v'"'"' is 1, or higher; and

a'"'"', s'"'"' are independently greater than or equal to 0, and a'"'"'+s'"'"' is greater than or equal to 1.

2. The composition of claim 1 wherein R_1'"'"' is an alkyl radical.

3. The composition of claim 2 wherein R_1'"'"' is an ethyl group.

4. The composition of claim 1 wherein the composition comprises at least one acrylic-containing group and at least one vinyl-containing group.

5. The composition of claim 4 wherein the acrylic-containing group is selected from the group consisting of an alkyl (meth)acrylate, alkyl (meth)acrylamide, fluoroalkyl(meth)acrylate, and fluoroalkyl(meth)acrylamide.

6. The composition of claim 5 wherein the alkyl (meth)acrylate or alkyl (meth)acrylamide group is selected from the group consisting of derivatives of 2-hydroxyethyl methacrylate, glycerol methacrylate, hydroxyethyl methacrylamide, N,N-dimethylacrylamide, and 2-methacrylamido ethanol.

7. The composition of claim 1 wherein at least one polysiloxane-containing group is linked to at least one polyalkylene ether-containing group through ester, carbonate, carbamate, urea or urethane linkages.

8. The composition of claim 4 wherein the vinyl-containing group is selected from the group consisting of vinyl carbonates, vinyl carbamates and vinyl ureas.

9. The composition of claim 8 wherein the vinyl-containing group is a vinyl carbonate.

10. The composition of claim 8 wherein the vinyl-containing group is a vinyl carbamate.

11. The composition of claim 8 wherein the vinyl-containing group is a vinyl urea.

12. The compound methacryloxyethyl vinyl carbonate.

13. The compound methacryloxyethyl vinyl carbamate.

14. The compound methacryloxyethyl vinyl urea.