Vinyl carbonate and vinyl carbamate contact lens material monomers

• US 5,610,252 A
• Filed: 05/25/1995
• Issued: 03/11/1997
• Est. Priority Date: 05/02/1989
• Status: Expired due to Term

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Seelye, David E., Bambury, Ronald E.
• Primary Examiner(s): Glass, Margaret W.
• Application Number:
  US08/450,510
• Time in Patent Office: 656 Days
• Field of Search: 526/279, 526/245, 526/286, 526/301, 526/314
• US Class Current: 526/279
• CPC Class Codes: C07C 2603/74 Adamantanes
• CPC Class Codes: C07C 271/14 to carbon atoms of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
• CPC Class Codes: C07C 271/16 to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 271/18 to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
• CPC Class Codes: C07C 271/20 to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
• CPC Class Codes: C07C 271/24 with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
• CPC Class Codes: C07C 271/28 to a carbon atom of a non-condensed six-membered aromatic ring
• CPC Class Codes: C07C 69/96 Esters of carbonic or haloformic acids
• CPC Class Codes: C07D 207/27 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 207/404 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
• CPC Class Codes: C07F 7/081 comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• 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: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C07F 7/1896 Compounds having one or more Si-O-acyl linkages
• CPC Class Codes: C08F 18/24 Esters of carbonic or haloformic acids
• CPC Class Codes: C08F 218/24 Esters of carbonic or haloformic acids, e.g. allyl carbonate
• CPC Class Codes: C08F 30/08 containing silicon
• CPC Class Codes: C08L 31/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid of hydrolysed polymers C08L29/00; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Novel monomers of the general formula ##STR1## where b is 0 or 1, a is 1, 2, 3 or 4, R² is a monovalent alkyl radical and R is an organic radical. The novel monomers may be employed to produce novel copolymers useful as hydrogel, soft non-hydrogel and/or rigid gas permeable contact lens materials.

Claims

1. A contact lens formed of a copolymer prepared by polymerizing a prepolymer mixture comprising:

(a) a monomer of the general formula (I);

##STR62## wherein;

a is 1, 2, 3 or 4;

b is 0 or 1;

X is --O--, --S--, or --NR³ --;

R is an organic radical;

R² is H or CH_3;

and

R³ is H or a monovalent alkyl radical; and

(b) a crosslinking agent.

2. A contact lens of claim 1, wherein monomer (a) is a compound of the general formula (I) wherein a is 1.

3. A contact lens of claim 2, wherein the crosslinking agent is a monomer of the general formula (II):

##STR63## wherein;

X is --O--, --S-- or --NR³ --;

R¹ is a multivalent organic radical;

R² is independently --H or --CH₃ ;

R³ is independently --H or a monovalent alkyl radical;

a is 2, 3 or 4; and

b is 0 or 1.

4. A contact lens of claim 1, wherein monomer (a) is a compound of the general formula (I) wherein b is 0.

5. A contact lens of claim 4, wherein monomer (a) is a compound of the general formula (I) wherein b is 0, a is 1 and R is a monofunctional organic radical.

6. A contact lens of claim 4, wherein monomer (a) is a compound of the general formula (I) wherein R is an organosilicon radical.

7. A contact lens of claim 4, wherein monomer (a) is 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate.

8. A contact lens of claim 4, wherein monomer (a) is 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate.

9. A contact lens of claim 4, wherein monomer (a) is 3-(vinyloxycarbonylthio)propyl[tris(trimethylsiloxy)silane].

10. A contact lens of claim 4, wherein monomer (a) is 3-(trimethylsilyl)propyl vinyl carbonate.

11. A contact lens of claim 4, wherein monomer (a) is trimethylsilylmethyl vinyl carbonate.

12. A contact lens of claim 4, wherein monomer (a) is trimethylsilylethyl vinyl carbonate.

13. A contact lens of claim 4, wherein monomer (a) is 4-t-butylphenyl vinyl carbonate.

14. A contact lens of claim 4, wherein monomer (a) is t-butyldimethylsiloxyethyl vinyl carbonate.

15. A contact lens of claim 4, wherein monomer (a) is 4-t-butylphenyl vinyl carbamate.

16. A contact lens of claim 4, wherein monomer (a) is 2,2,2-trifluoroethyl vinyl carbonate.

17. A contact lens of claim 4, wherein monomer (a) is 2,2,2-trifluoroethyl vinyl carbamate.

18. A contact lens of claim 4, wherein monomer (a) is 1,1,1,3,3,3-hexafluoro-2-propyl vinyl carbonate.

19. A contact lens of claim 4, wherein monomer (a) is 2,2,2-trifluoro-1-phenylethyl vinyl carbonate.

20. A contact lens of claim 4, wherein monomer (a) is 2-hydroxyethyl vinyl carbonate.

21. A contact lens of claim 4, wherein monomer (a) is 2-hydroxyethyl vinyl carbamate.

22. A contact lens of claim 5, wherein the crosslinking agent is of the formula:

##STR64## where x is on average 26.

23. A contact lens of claim 3, wherein the crosslinking agent is a compound described by the general formula (II) where a equals 2, and R¹ is of the formula:

##STR65## where x and z are 1 to 6, y is on average between 2 and 200, and R" is an alkyl radical or a fluorinated alkyl radical.

24. A contact lens of claim 4, wherein monomer (a) is selected from the group consisting of 4-(t-butyl)cyclohexyl vinyl carbonate, 1-adamantane vinyl carbonate, 1-adamantane methyl vinyl carbonate, 1-adamantane ethyl vinyl carbonate, 1-adamantane vinyl carbamate, and 2,2,2-trifluoro-1-phenylethyl vinyl carbonate.

25. A contact lens of claim 1, wherein the crosslinking agent is selected from the group consisting of propargyl vinyl carbamate, 1,2-bis-(vinyloxycarbonyloxy)ethane, α

-ω

-bis-(vinyloxycarbonyl)triethylene glycol, α

-ω

-bis(vinyloxycarbonyl)polyethylene glycol, α

-ω

-bis (vinyloxycarbonyl)polypropylene glycol, 2,2-dimethyl-1,3-bis-(vinyloxycarbonyloxy)propane, N,O-bis-(vinyloxycarbonyl)-ethanolamine, 2,2-dimethyl-N,N-bis-(vinyloxycarbonyl)-1,3-propanediamine, and 1,5-bis-(vinyloxycarbonyloxy)-2,2,3,3,4,4-hexafluoropentane.

26. A contact lens of claim 1, wherein the monomer and crosslinking agent are copolymerizable by free-radical polymerization and the crosslinking agent contains ethylenic unsaturation.