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US 4,401,797 AGranted
Copolymers and hydrogels: process and articles made thereof
AssigneeSyntex (U.S.A.) Inc.
InventorPaul M. Gallop
Life of this patent
Estimating the term…
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.
Claims14
A polymer formed by a free radical bulk polymerization of:
- (a) a first monomer of the formula:
- ##STR29## wherein:
- R.sub.1 is hydrogen or methyl;
- m is an integer from 1 to 4;
- and
- n is an integer from 0 to 1;
- 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:
- (i) >B--R.sub.3
- 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;
- and
- (ii) >S.dbd.O
- (b) a second substantially water insoluble monomer of the formula:
- ##STR30## 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
- (c) optionally, a third substantially water insoluble monomer of the formula:
- ##STR31## wherein:
- R.sub.9 is hydrogen or methyl;
- and
- p is an integer from 1 to 6;
- or ##STR32## wherein:
- R.sub.10 and R.sub.11 are independently hydrogen or methyl, and
- q is an integer from 1 to 6;
- the concentration of said third monomer when present being between about 0 and 30 percent by weight of the first monomer;
- said protection group(s) being subsequently removable by chemical means after said bulk polymerization;
- wherein said polymer can be handled, machined, and shaped over a wide humidity range as compared to a hydrogel polymer and can be polished and machined using water based and water-compatible oils, abrasives and polishes.
33 more elements
A polymer formed by a free radical bulk polymerization of:
- (a) a first monomer of the formula:
- ##STR33## wherein:
- R.sub.1 is hydrogen or methyl;
- R.sub.3 is lower alkyl containing 1 to 6 carbon atoms or cycloalkyl having from 3 to 6 carbon atoms and aryl selected from the group consisting of phenyl, tolyl and naphthyl;
- and
- m is an integer from 1 to 4;
- n is an integer from 0 to 1;
- (b) a second substantially water insoluble monomer of the formula:
- ##STR34## 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
- (c) optionally a third substantially water insoluble monomer of the formula:
- ##STR35## wherein:
- R.sub.9 is hydrogen or methyl;
- and
- p is an integer from 1 to 6;
- the concentration of said third monomer when present being between about 0.1 and 30 percent by weight of the first monomer;
- wherein said polymer can be handled, machined, and shaped over a wide humidity range as compared to a hydrogel polymer and can be polished and machined using water-based and water compatible oils, abrasives and polishes.
18 more elements
A polymer formed by a free radical bulk polymerization of:
- (a) a first monomer of the formula:
- ##STR36## wherein:
- R.sub.1 is hydrogen or methyl;
- R.sub.2 is lower alkyl containing 1 to 6 carbon atoms;
- and
- m is an integer from 1 to 4;
- n is an integer from 0 to 1;
- (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
- (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;
- the concentration of said third monomer being between about 0.001 and 30 percent by weight of the first monomer;
- said boron protecting group being subsequently removable by chemical means after said bulk polymerization.
18 more elements
A process for preparing a polymer which comprises:
- (a) treating a monomer of the formula:
- ##STR39## wherein:
- R.sub.1 is hydrogen or methyl;
- and
- m is an integer from 0 to 6 or cycloalkyl containing from 3 to 6 carbon atoms;
- n is an integer from 0 to 1;
- with a boronic acid of the formula:
- R.sub.3 B(OH).sub.2
- wherein:
- R.sub.3 is lower alkyl containing 1 to 6 carbon atoms or aryl selected from the group consisting of phenyl tolyl and naphthyl to form an adduct of the formula:
- ##STR40## wherein B, R.sub.1, R.sub.2, m and n are defined above and ##STR41## corresponds to a boron-containing protecting group;
- (b) purifying said adduct using non-aqueous, non-hydroxylic organic solvents;
- (c) mixing said purified adduct with a second monomer of the formula:
- ##STR42## (d) optionally mixing said purified adduct and second monomer with a third monomer of the formula:
- ##STR43## wherein:
- R.sub.9 is hydrogen or methyl;
- and
- r is an integer from 1 to 6;
- or a third monomer of the formula:
- ##STR44## wherein:
- R.sub.10 and R.sub.11 are independently hydrogen or methyl;
- and
- q is an integer from 1 to 6;
- (e) polymerizing by a free radical bulk polymerization process said mixture of said purified adduct and said monomer(s).
21 more elements
Dependencies are inferred from the claim text.