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

• US 4,454,295 A
• Filed: 07/25/1983
• Issued: 06/12/1984
• 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: Wittmann, Joseph W., Evans, John M.
• Primary Examiner(s): Kight, III, John
• Assistant Examiner(s): Nutter, Nathan M.
• Application Number:
  US06/517,166
• Time in Patent Office: 323 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
• US Class Current: 527/311
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 230/08 containing silicon
• 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 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 composition of claim 1 which contains about 1 to about 35% by weight of said silicone ester.

3. The composition of claim 1 which contains about 5 to about 15% by weight of said silicone ester.

4. The composition of claim 1 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 allyl group, and mixtures thereof.

5. The composition of claim 1 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.

6. The composition of claim 1 wherein said silicone ester is represented by the formula:

##STR28## 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^III 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.

7. The composition of claim 1 wherein said silicone ester is represented by the formula:

##STR29## 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.

8. The composition of claim 1 wherein said silicone ester is represented by the formula:

##EQU2## 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.

9. The composition of claim 1 wherein said silane monomer is represented by the formula:

##STR30## wherein R⁷ is vinyl or allyl;

each R⁸ individually is a monovalent saturated

alipahtic 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.

10. The composition of claim 1 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.

11. The composition of claim 1 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.

12. A process for obtaining a cured transparent cellulose ester composition which comprises subjecting the composition of claim 1 to ultraviolet light in the range of about 200 to 800 nm, or fluorescent radiation in the range of about 200 to 800 nm, or to γ

-irradiation for a time sufficient to cause curing of said composition.