# US 4,395,496 A · Cured cellulose ester, method of curing same, and use thereof

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- Number: US 4,395,496 A
- Document ID: US4395496A
- Status: Granted
- Kind: A
- Application number: 06/321,506
- Filed: 1981-11-16
- Granted: 1983-07-26
- Earliest claimed: 1981-11-16
- Assignees: UCO Optics, Inc.
- Inventors: Joseph W. Wittmann; John M. Evans
- Web page: https://patentgrep.com/patent/US4395496A

## CPC

- G02B 1/043: {Contact lenses}
- C08F 251/02: on to cellulose or derivatives thereof
- Y10S 525/937: Utility as body contact e.g. implant, contact lens or I.U.D.
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Cellulose esters are cured by exposure to radiation preferably followed by exposure to elevated temperatures of at least about 100.degree. 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

### Claim 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.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1, 2)

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.

### Claim 4 (depends on 3)

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

### Claim 5 (depends on 3)

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

### Claim 6 (depends on 3)

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

### Claim 7 (depends on 3)

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

### Claim 8 (depends on 3)

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

### Claim 9 (depends on 1, 2)

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

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 1)

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

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 2)

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.

### Claim 14 (depends on 2)

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

### Claim 15 (depends on 2)

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.

### Claim 16 (depends on 2)

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.

### Claim 17 (depends on 2)

The contact lens of claim 2 wherein said silicone ester is represented by the formula: ##STR24## wherein R is hydrogen or methyl;
each R.sup.I individually is methyl, phenyl or O--SiR.sub.3.sup.II ;
each R.sup.II individually is methyl or phenyl;
R.sup.IIII is SiR.sup.II and R.sup.IV is OSiR.sub.3.sup.II ; or
R.sup.III and R.sup.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.

### Claim 18 (depends on 2)

The contact lens of claim 2 wherein said silicone ester is represented by the formula: ##STR25## wherein R is H or methyl;
each R.sup.2 individually is CH.sub.3, phenyl or O--Si(CH.sub.3).sub.3 ;
each R.sup.3 individually is CH.sub.3 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.

### Claim 19 (depends on 2)

The contact lens of claim 2 wherein said silicone ester is represented by the formula: ##STR26## wherein R is H or methyl;
R.sup.4 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 R.sup.5 is CH.sub.3 ; R.sup.6 is CH.sub.3 O.sub.0.5 or (CH.sub.3).sub.3 SiO.sub.0.5 ;
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.

### Claim 20 (depends on 19)

The contact lens of claim 19 wherein R.sup.4 is an alkylene bridge.

### Claim 21 (depends on 2)

The contact lens of claim 2 wherein said silane monomer is represented by the formula: ##STR27## wherein R.sup.7 is vinyl or alkyl;
each R.sup.8 individually is a monovalent saturated aliphatic hydrocarbon radical or a monovalent aromatic hydrocarbon radical;
each R.sup.9 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.

### Claim 22 (depends on 21)

The contact lens of claim 21 wherein R.sup.8 is an alkyl radical of from 1 to 6 carbon atoms or an aryl radical containing 6-10 carbon atoms, and R.sup.9 is an alkyl radical containing 1-6 carbon atoms.

### Claim 23 (depends on 2)

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.

### Claim 24 (depends on 2)

The contact lens of claim 2 wherein said silicone ester is selected from the group of .gamma.-pentamethyldisiloxanylpropyl methacrylate, tris (trimethylsiloxy)-.alpha.-methacryloxypropyl silane, heptamethylcyclotetrasiloxyanyl methylmethacrylate, methyl-di (trimethylsiloxy) sylyl propyl glycerol methacrylate, pentamethyldisiloxanyl (propyl glycerol) monomethacrylate, pentamethyldisiloxanyl (propyl glycerol) ethylene glycol monomethacrylate, and mixtures thereof.

### Claim 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.

### Claim 26 (depends on 25)

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

### Claim 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.

### Claim 28 (depends on 27)

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