US 4,634,722 AGranted

Copolymers and hydrogels: process and articles made thereof

AssigneeSyntex (U.S.A.) Inc.

InventorPaul M. Gallop

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Abstract

Copolymers having improved machining and water resistant properties are produced using a monomer containing an adduct protecting group, particularly an alkyl boronic acid adduct, of glyceryl acrylate or glyceryl methacrylate, in combination with an alkyl acrylate or methacrylate, and optionally a glycidyl acrylate or methacrylate. After machining and shaping, the adduct is removed to provide a hydrogel useful as a contact lens material.

Claims16

Dependent claims

A process for making a hydrogel contact lens, comprising the steps of:

(A) forming a button from a polymer material, said polymer material being a free radical bulk polymerization product of:
(a) a first monomer of the formula:
##STR32## wherein:
R.sub.1 is hydrogen or methyl;
m is an integer from 1 to 4;
n is an integer from 0 to 1;
and
X and Y are protecting groups and are independently selected from the group consisting of:
(1) --C(O)OR.sub.2
wherein R.sub.2 is an alkyl group containing from 1 to 8 carbon atoms;
(2) hexahydropyranyl;
and
(3) where X and Y together form one protecting group, selected from the group consisting of:
##STR33## wherein R.sub.3 is a lower alkyl group containing 1 to 6 carbon atoms, cycloalkyl group containing 3 to 6 carbon atoms;
and aryl selected from the group consisting of phenyl, tolyl and naphthyl;
##STR34## wherein R.sub.4 and R.sub.5 are independently hydrogen and lower alkyl groups containing from 1 to 6 carbon atoms and together may form a cyclic ring containing from 2 to 6 carbon atoms;
##STR35## wherein R.sub.6 is a lower alkyl group containing from 1 to 6 carbon atoms;
and ##STR36## (b) a second, substantially water insoluble monomer of the formula:
##STR37## wherein:
R.sub.7 is hydrogen or methyl;
and
R.sub.8 is lower alkyl having 1 to 6 carbon atoms or cycloalkyl having from 3 to 6 carbon atoms;
the molar ratio of said first monomer to said second monomer being between about 1:30 and 20:1;
and, optionally,
(c) a third, substantially water insoluble monomer of the formula:
##STR38## wherein:
R.sub.9 is hydrogen or methyl;
and
p is an integer from 1 to 6;
or of the formula:
##STR39## wherein:
R.sub.10 and R.sub.11 are independently hydrogen or methyl, and
q is an integer from 0 to 5;
the concentration of said third monomer, when present, being between about 0 and 30 percent by weight of the first monomer;
(B) machining, shaping and polishing said button into the shape of a contact lens, using water compatible oils, abrasives and polishes;
and
(C) removing said protecting group(s) from said polymer button, as formed into the shape of a contact lens, by chemical means and replacing said protecting group(s) with hydroxyl groups.

34 more elements

A process for making a hydrogel contact lens, comprising the steps of:

(A) forming a button from a polymer material, said polymer material being a free radical bulk polymerization product of:
(a) a first monomer of the formula:
##STR40## wherein:
R.sub.1 is hydrogen or methyl;
m is an integer from 1 to 4;
n is an integer from 0 to 1;
and
X and Y are protecting groups and are independently selected from the group consisting of:
(1) --C(O)OR.sub.2
wherein R.sub.2 is alkyl group containing from 1 to 8 carbon atoms;
(2) hexahydropyranyl;
and
(3) where X and Y together form one protecting group, selected from the group consisting of:
##STR41## wherein R.sub.3 is a lower alkyl group containing 1 to 6 carbon atoms, cycloalkyl group containing 3 to 6 carbon atoms;
and aryl selected from the group consisting of phenyl, tolyl and naphthyl;
##STR42## wherein R.sub.4 and R.sub.5 are independently hydrogen and lower alkyl groups containing from 1 to 6 carbon atoms and together may form a cyclic ring containing from 2 to 6 carbon atoms;
##STR43## wherein R.sub.6 is a lower alkyl group containing from 1 to 6 carbon atoms;
and ##STR44## (b) a second, substantially water insoluble monomer of the formula:
##STR45## wherein:
R.sub.7 is hydrogen or methyl;
and
R.sub.8 is lower alkyl having 1 to 6 carbon atoms or cycloalkyl having from 3 to 6 carbon atoms;
the molar ratio of said first monomer to said second monomer being between about 1:30 and 20:1;
and, optionally,
(c) a third, substantially water insoluble monomer of the formula:
##STR46## wherein:
R.sub.9 is hydrogen or methyl;
and
p is an integer from 1 to 6;
or of the formula:
##STR47## wherein:
R.sub.10 and R.sub.11 are independently hydrogen or methyl, and
q is an integer from 0 to 5;
the concentration of said third monomer, when present, being between about 0 and 30 percent by weight of the first monomer;
and
(B) machining, shaping and polishing said button into the shape of a contact lens, using water compatible oils, abrasives and polishes.

33 more elements

Dependencies are inferred from the claim text.

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Abstract

A process for making a hydrogel contact lens, comprising the steps of:

(A) forming a button from a polymer material, said polymer material being a free radical bulk polymerization product of:
(a) a first monomer of the formula:
##STR32## wherein:
R.sub.1 is hydrogen or methyl;
m is an integer from 1 to 4;
n is an integer from 0 to 1;
and
X and Y are protecting groups and are independently selected from the group consisting of:
(1) --C(O)OR.sub.2
wherein R.sub.2 is an alkyl group containing from 1 to 8 carbon atoms;
(2) hexahydropyranyl;
and
(3) where X and Y together form one protecting group, selected from the group consisting of:
##STR33## wherein R.sub.3 is a lower alkyl group containing 1 to 6 carbon atoms, cycloalkyl group containing 3 to 6 carbon atoms;
and aryl selected from the group consisting of phenyl, tolyl and naphthyl;
##STR34## wherein R.sub.4 and R.sub.5 are independently hydrogen and lower alkyl groups containing from 1 to 6 carbon atoms and together may form a cyclic ring containing from 2 to 6 carbon atoms;
##STR35## wherein R.sub.6 is a lower alkyl group containing from 1 to 6 carbon atoms;
and ##STR36## (b) a second, substantially water insoluble monomer of the formula:
##STR37## wherein:
R.sub.7 is hydrogen or methyl;
and
R.sub.8 is lower alkyl having 1 to 6 carbon atoms or cycloalkyl having from 3 to 6 carbon atoms;
the molar ratio of said first monomer to said second monomer being between about 1:30 and 20:1;
and, optionally,
(c) a third, substantially water insoluble monomer of the formula:
##STR38## wherein:
R.sub.9 is hydrogen or methyl;
and
p is an integer from 1 to 6;
or of the formula:
##STR39## wherein:
R.sub.10 and R.sub.11 are independently hydrogen or methyl, and
q is an integer from 0 to 5;
the concentration of said third monomer, when present, being between about 0 and 30 percent by weight of the first monomer;
(B) machining, shaping and polishing said button into the shape of a contact lens, using water compatible oils, abrasives and polishes;
and
(C) removing said protecting group(s) from said polymer button, as formed into the shape of a contact lens, by chemical means and replacing said protecting group(s) with hydroxyl groups.

34 more elements