Polymeric compositions useful in oxygen permeable contact lenses

• US 5,032,658 A
• Filed: 10/17/1989
• Issued: 07/16/1991
• Est. Priority Date: 10/17/1989
• Status: Expired due to Term

• Current Assignee: B&L International Holdings Corp.
• Original Assignee: Polymer Technology Group, Inc. (DSM-Firmenich AG)
• Inventors: Rothenberger, Scott D., Baron, Richard C.
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): Sarofin, N.
• Application Number:
  US07/422,612
• Time in Patent Office: 637 Days
• Field of Search: 526/321, 526/279, 526/318, 526/325, 526/328.5, 526/245, 526/247, 526/242, 350/409
• US Class Current: 526/321
• CPC Class Codes: C08L 33/06 of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
• CPC Class Codes: C08L 35/00 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 a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Carboxylic acid esters devoid of beta hydrogens are homopolymerized or copolymerized with contact lens organic materials to form desirable contact lens materials and contact lenses. These materials have good contact lens properties, including desirable DK values, hardness, machineability and a desirable refractive index of at least 1.

Claims

1. A contact lens material formed from the free radical polymerization of a contact lens organic material and a carboxylic acid ester derived from at least one alcohol which is devoid of beta hydrogens in an amount predetermined to provide both a desired hardness value and oxygen permeability to said contact lens material, wherein said ester has the following formula:

##STR14## wherein A is selected from the group consisting of mesaconic acid, itaconic acid, citraconic acid, methylene malonate, maleic acid, fumaric acid, ethylene tricarboxylic acid, acrylic acid, and methacrylic acid,

n=1, 2 or 3,

R₁, R₂ and R₃ are the same or different and each are alkyl, cycloalkyl or aryl groups having from 1 to 10 carbon atoms or ether groups having from 2 to 10 carbon atoms,

where when A is derived from a dibasic or tribasic acid, the ester can be a full ester, half ester, partial ester or can be a mixed ester, said ester being derived from at least one alcohol which is devoid of beta hydrogens,

said material having a Shore D hardness of at least 70 and a DK of at least 10.

2. A contact lens material in accordance with claim 1, where said contact lens organic material is selected from the group consisting of:

(a) an ethylenically unsaturated organosilicone having the following formula;

##EQU2## Wherein;

"X" the ethylenically unsaturated group is chosen from among;

vinyl

acryloxy

methacryloxy

vinyloxy

carbovinyloxy

"Y" the divalent radical is either no group or

methylene

ethylene

propylene

propenylene

butylene

cyclohexylene

phenylene

--CH₂ CH(OH)CH₂ OCH₂ CH₂ CH₂ --

--CH₂ CH₂ OCH₂ CH(OH)CH₂ CH₂ CH₂

"a" is an integer from 1 to 4

"n" is an integer from 4 to 20

"b" is an integer from 0 to 3 and may be the same or different for each "i" group

"R" may be the same or different within each "i" moiety and is selected from among;

vinyl

methyl

ethyl

propyl

butyl

cyclohexyl

phenyl

2-acetoxyethyl

3-acetoxypropyl

2-(carbomethoxy) ethyl

3-(carbomethoxy) propyl

3 - hydroxypropyl

4 - hydroxybutyl

3,3,3,-trifluoropropyl

3-(heptafluoroisopropoxy) propyl

pentafluorophenyl

(b) fluorosilicone acrylates;

(c) fluoroacrylates;

(d) fluoropolyethers;

(e) hema type materials;

(f) styrene polymers; and

(g) mixtures thereof.

3. A contact lens material in accordance with claim 2 wherein said carboxylic acid ester is an ester which has a desired hardness and a DK of at least 10 when homopolymerized by free radical polymerization in a polymer having a number average molecular weight of at least 50,000.

4. A contact lens material in accordance with claim 3, wherein said ester is a monocarboxylic acid ester selected from the group consisting of acrylates, methacrylates and mixtures thereof.

6. A contact lens material in accordance with claim 3, wherein said ester is a tribasic acid ester.

14. A contact lens in accordance with claim 1, wherein said ester is dineopentyl maleate.

15. A contact lens in accordance with claim 1, wherein said ester is dineopentyl methylenemalonate.

16. A contact lens in accordance with claim 1, wherein said ester is dineopentyl.

17. A contact lens in with claim 1, wherein said ester is dineopentyl mesaconate.

5. A contact lens material in accordance with C-aim 3, wherein said ester is a dicarboxylic ester selected from the group consisting of mesaconates, itaconates, citraconates, maleates, methylene malonates and fumarates.

7. A contact lens formed substantially of an ester of the free radical polymerization product of a polymerizable carboxylic acid ester having the following formula:

##STR15## Wherein;

A is selected from the group consisting of mesaconic acid, itaconic acid, citraconic acid, methylene malonate, maleic acid, fumaric acid, ethylene tricarboxylic acid, acrylic acid, and methacrylic acid,

n=1, 2, or 3

R₁, R₂ and R₃ are the same or different and each are alkyl, cycloalkyl or aryl groups having from 1 to 10 carbon atoms or ether groups having from 2 to 10 carbon atoms,

where when A is derived from a dibasic or tribasic acid, the ester can be a full ester, half ester, partial ester or can be a mixed ester, said ester being derived from at least one alcohol which is devoid of beta hydrogens,

said lens having a Shore D hardness of at least 70 and a DK of at least 10 with a number average molecular weight of at least 50,000.

8. A contact lens in accordance with claim 7, and further comprising at least one modifier selected from the group consisting of wetting agents, crosslinking agents, permeability enhancers, physical property modifiers, and combinations thereof.

9. A contact lens in accordance with claim 7, having a DK of at least 15.

10. A contact lens in accordance with claim 7, wherein said ester is dineopentyl itaconate.

11. A contact lens in accordance with claim 7, wherein said ester is dineopentyl fumarate.

12. A contact lens in accordance with claim 7, wherein said ester is neopentyl methacrylate.

13. A contact lens in accordance with claim 7, wherein said ester is neopentyl acrylate.

18. A polymerized contact lens material formed by free radical polymerization of a wetting agent in an amount of from 1 to 10% by weight, a silicone methacrylate in an amount of from 0 to 60%, a crosslinking agent in an amount of 0 to 30% and dineopentyl itaconate in an amount of 10 to 80%.

19. A polymerized contact lens material formed by free radical polymerization of methacrylic acid, n-vinyl pyrrolidone, methacryloyloxypropyl tris (trimethylsilyl) siloxane, tetraethylene glycol dimethacrylate, and dineopentyl itaconate.

20. A polymerized contact lens material formed by free radical polymerization of a wetting agent 0-10% by weight, a crosslinking agent 0-30% by weight, a fluorinated itaconate 0-60% by weight, a fluorinated methacrylate 0-60% by weight, a silicone methacrylate 0-60% by weight, and dineopentyl itaconate 10-80% by weight.

21. A polymerized contact lens material formed by free radical polymerization of methacrylic acid, n-vinyl pyrrolidone, neopentyl glycol dimethacrylate, methacryloyloxypropyl tris (trimethylsilyl) siloxane, bis-hexafluoro isopropyl itaconate, hexafluoroisopropylmethacrylate and dineopentyl itaconate.

22. A polymerized contact lens material formed by free radical polymerization of a wetting agent 0-10% by weight, dineopentyl itaconate 10-80% by weight, a fluoroalkyl methacrylate 0-60% by weight, a fluoroalkyl itaconate 0-60% by weight, and a crosslinking agent 0-30% by weight.

23. A polymerized contact lens material formed by free radical polymerization of n-vinyl pyrrolidone, dineopentyl itaconate, hexafluoro isopropyl methacrylate, bis-hexa fluoro isopropyl itaconate and neopentyl glycol dimethacrylate.