Cured cellulose ester, method of curing same, and use thereof

• US 4,395,496 A
• Filed: 11/16/1981
• Issued: 07/26/1983
• Est. Priority Date: 11/16/1981
• Status: Expired due to Fees

• Current Assignee: The Cooper Companies Incorporated
• Original Assignee: CooperVision Incorporated (The Cooper Cos., Inc.)
• Inventors: Evans, John M., Wittmann, Joseph W.
• Primary Examiner(s): Kight, III, John
• Assistant Examiner(s): Nutter, Nathan M.
• Application Number:
  US06/321,506
• Time in Patent Office: 617 Days
• Field of Search: 523/106, 523/107, 525/54.21, 525/54.23, 525/937, 527/311, 527/313, 527/314, 528/32, 528/33, 528/43, 351/160 R, 351/160 H
• US Class Current: 523/107
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 230/085 the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
• CPC Class Codes: C08F 251/02 on to cellulose or derivatives thereof
• CPC Class Codes: C08L 1/00 Compositions of cellulose, modified cellulose or cellulose derivatives
• CPC Class Codes: C08L 51/00 Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds for ABS polymers C08L55/02; Compositions of derivatives of such polymers
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: Y10S 525/937 Utility as body contact e.g. implant, contact lens or I.U.D.

Abstract

Cellulose esters are cured by exposure to radiation preferably followed by exposure to elevated temperatures of at least about 100° C. In addition, polymers obtained from reacting certain cellulose esters with certain polymerizable silicon esters are provided. The cured cellulose esters are suitable for producing transparent parts such as contact lenses.

Claims

1. A shaped transparent contact lens of concavo-convex shape with the concave surface substantially conforming to the cornea of the eye, said lens being formed of a composition from the polymerization of a composition comprising an organic cellulose ester selected from the group of cellulose acetate, cellulose acetate butyrate, cellulose acetate propionate or mixtures thereof;

and a polymerizable ethylenically unsaturated silicone ester.

2. The contact lens of claim 1 wherein said composition contains up to about 35% by weight of said silicone ester.

3. The contact lens of claim 1 or 2 wherein said composition can contain up to about 10% by weight of a crosslinking agent, up to about 10% by weight of a photoinitiator, up to about 2% by weight of an antioxidant, and up to about 30% by weight of an auxiliary plasticizer.

4. The contact lens of claim 3 wherein said composition contains about 0.1 to about 5% by weight of a crosslinking agent.

5. The contact lens of claim 3 wherein said composition contains about 0.1 to about 10% by weight of a photoinitiator.

6. The contact lens of claim 3 wherein said composition contains about 0.1 to about 5% by weight of a photoinitiator.

7. The contact lens of claim 3 wherein said composition contains about 5 to about 15% by weight of an auxiliary plasticizer.

8. The contact lens of claim 3 wherein said composition contains about 0.1 to about 1% by weight of an antioxidant.

9. The contact lens of claim 1 or 2 wherein said cellulose ester is cellulose acetate butyrate.

10. The contact lens of claim 1 wherein said composition contains up to about 35% by weight of said silicone ester.

11. The contact lens of claim 1 wherein said composition contains about 1 to about 35% by weight of said silicone ester.

12. The contact lens of claim 1 wherein said composition contains about 5 to about 15% by weight of said silicone ester.

13. The contact lens of claim 2 wherein said silicone ester is selected from the group of silicone esters of ethylenically unsaturated carboxylic acids, silane monomers containing vinyl group, silane monomers containing alkyl group, and mixtures thereof.

14. The contact lens of claim 2 wherein said silicone ester is monoethylenically unsaturated.

15. The contact lens of claim 2 wherein said silicone ester is a silicone ester of an ethylenically unsaturated carboxylic ester, and wherein said carboxylic acid is an aliphatic monocarboxylic and monoethylenic acid.

16. The contact lens of claim 2 wherein said silicone ester is a silicone ester of an ethylenically unsaturated carboxylic acid selected from the group of acrylic acid, methacrylic acid, crotonic acid, and mixtures thereof.

17. The contact lens of claim 2 wherein said silicone ester is represented by the formula:

##STR24## wherein R is hydrogen or methyl;

each R^I individually is methyl, phenyl or O--SiR₃^II ;

each R^II individually is methyl or phenyl;

R^IIII is SiR^II and R^IV is OSiR₃^II ;

or

R^III and R^IV together form a single bond to form a cyclic ring;

each a, b, and c individually is an integer of 0-3;

p is an integer of 2-4;

q is an integer of 0-20;

n is an integer of 1-3; and

r is an integer of 0-1.

18. The contact lens of claim 2 wherein said silicone ester is represented by the formula:

##STR25## wherein R is H or methyl;

each R² individually is CH₃, phenyl or O--Si(CH₃)₃ ;

each R³ individually is CH₃ or phenyl;

each a, b, and c individually is an integer of 0-3;

p is an integer of 2-4;

q is an integer of 0-20;

n is an integer of 1-3; and

r is an integer of 0-1.

19. The contact lens of claim 2 wherein said silicone ester is represented by the formula:

##STR26## wherein R is H or methyl;

R⁴ is a divalent hydrocarbon radical having 1-10 carbon atoms, or a divalent hydrocarbon bridge having 1-10 carbon atoms and being broken by oxygen linkage;

each R⁵ is CH₃ ;

R⁶ is CH₃ O₀.5 or (CH₃)₃ SiO₀.5 ;

each d is an integer of 0-2;

e is an integer of 1-3 and f is an integer of 0-100, and provided that when f is 0, d is at least 1.

20. The contact lens of claim 19 wherein R⁴ is an alkylene bridge.

21. The contact lens of claim 2 wherein said silane monomer is represented by the formula:

##STR27## wherein R⁷ is vinyl or alkyl;

each R⁸ individually is a monovalent saturated aliphatic hydrocarbon radical or a monovalent aromatic hydrocarbon radical;

each R⁹ is an alkyl radical;

g is an integer of 0-2;

h is an integer of 1-3; and

the sum of g and h is 3.

22. The contact lens of claim 21 wherein R⁸ is an alkyl radical of from 1 to 6 carbon atoms or an aryl radical containing 6-10 carbon atoms, and R⁹ is an alkyl radical containing 1-6 carbon atoms.

23. The contact lens of claim 2 wherein said silane monomer is selected from the group of vinyl triethoxy silane, vinyl trimethoxy silane, vinyl phenol dimethoxy silane, vinyl tributoxy silane, and mixtures thereof.

24. The contact lens of claim 2 wherein said silicone ester is selected from the group of γ

-pentamethyldisiloxanylpropyl methacrylate, tris (trimethylsiloxy)-α

-methacryloxypropyl silane, heptamethylcyclotetrasiloxyanyl methylmethacrylate, methyl-di (trimethylsiloxy) sylyl propyl glycerol methacrylate, pentamethyldisiloxanyl (propyl glycerol) monomethacrylate, pentamethyldisiloxanyl (propyl glycerol) ethylene glycol monomethacrylate, and mixtures thereof.

25. A blank from which a transparent contact lens of concavo-convex shape can be lathed wherein said blank or button is formed of a composition from the polymerization of a composition comprising an organic cellulose ester selected from the group of cellulose acetate, cellulose acetate butyrate, cellulose acetate propionate, or mixtures thereof;

and a polymerizable ethylenically unsaturated silicone ester.

26. The blank of claim 25 wherein said composition contains about 1 to about 35% by weight of said silicone ester.

27. A rod from which blanks or buttons can be cut and from which a shaped transparent contact lens of concavo-convex shape can be lathed, wherein said rod is formed of a composition from the polymerization of a composition comprising an organic cellulose ester selected from the group of cellulose acetate, cellulose acetate butyrate, cellulose acetate propionate, or mixtures thereof;

and a polymerizable ethylenically unsaturated silicone ester.

28. The rod of claim 27 wherein said composition contains about 1 to about 35% by weight of said silicone ester.