US 6,025,026 AGranted

Process for producing an adherent polymeric layer on polymeric substrates and articles produced thereby

AssigneeTransitions Optical, Inc.

InventorsRobert A. Smith, Robert W. Walters, Kevin J. Stewart, Michael S. Misura

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Abstract

Described is a process for producing adherent layer(s) on organic polymeric substrates following the steps of (a) treating the surface of the polymeric substrate to provide reactive groups; (b) applying to the surface a polymerizable composition of organic anhydrides, isocyanates and/or a mixture thereof that is substantially free of organosiloxanes; and (c) curing the polymerizable coating. Further steps include applying an additional layer which is substantially free of organosiloxanes and that may or may not contain the polymerizable composition of the present invention. Also described are products produced by the process that may be transparent, tinted, tinted and polarized or photochromic.

Claims32

Dependent claims

A process for producing an adherent polymeric layer on an organic polymeric substrate, which comprises the steps of:

a. treating the surface of said polymeric substrate to provide reactive groups at said surface;
b applying to the surface of the treated substrate a polymerizable composition consisting essentially of a composition selected from the group consisting of:
(i) organic anhydride(s) having at least one polymerizable ethylenic linkage;
(ii) isocyanate(s) selected from the group consisting of:
(a) isocyanate represented by the following general formula:
CH.sub.2 .dbd.C(Y)--C(O)OR'--N.dbd.--C.dbd.O
wherein Y is selected from the group consisting of hydrogen and C.sub.1 -C.sub.5 alkyl;
and R' is a C.sub.1 -C.sub.20 alkylene or phenylene;
(b) m-isopropenyl-.alpha., .alpha.-dimethyl benzyl isocyanate;
(c) product of the reaction of acrylic functional monomer(s) containing a vinyl ether group and isocyanic acid;
(d) product of the reaction of unsaturated monomer(s) having a functional group selected from the group consisting of amino, hydroxy, thio and a combination of said functional groups and isocyanate(s) having at least two functional isocyanate groups;
and
(e) mixtures of these isocyanates;
and
(iii) combination(s) of (i) and (ii);
and
c. curing the applied polymerizable composition.

14 more elements

A process for producing an adherent polymeric layer on an organic polymeric substrate, which comprises the steps of:

a. treating the surface of said polymeric substrate to provide reactive groups at said surfacer
b. applying to the surface of the treated substrate a polymerizable composition consisting essentially of from 0.01 to 10 weight percent, based on the total weight of the composition, of catalyst and an adhesion improving amount of a composition selected from the group consisting of:
(i) organic anhydride(s) having at least one polymerizable ethylenic linkage;
(ii) isocyanate(s) selected from the group consisting of:
(a) isocyanate represented by the following general formula:
CH.sub.2 .dbd.C(Y)--C(O)OR'--N.dbd.C.dbd.O
wherein Y is selected from the group consisting of hydrogen and C.sub.1 -C.sub.5 alkyl;
and R' is a C.sub.1 -C.sub.20 alkylene or phenylene;
(b) m-isopropenyl-.alpha., .alpha.-dimethyl benzyl isocyanate;
(c) product of the reaction of acrylic functional monomer(s) containing a vinyl ether group and isocyanic acid;
(d) product of the reaction of unsaturated monomer(s) having a functional group selected from the group consisting of amino, hydroxy, thio and a combination of said functional groups and isocyanate(s) having at least two functional isocyanate groups;
and
(e) mixtures of these isocyanates;
and
(iii) combination(s) of (i) and (ii);
and
c. curing the applied polymerizable composition.

14 more elements

A process for producing an adherent polymeric layer on an organic polymeric substrate, which comprises the steps of:

a. treating the surface of said polymeric substrate to provide reactive groups at said surface;
b. applying to the surface of the treated substrate a polymerizable composition consisting essentially of at least 5 weight percent, based on the total weight of said composition, of non-functional unsaturated monomer(s), from 0.1 to 40 weight percent, based on the total weight of the composition, of photochromic compound(s), from 0.01 to 10 weight percent, based on the total weight of the composition, of catalyst and an adhesion improving amount of the isocyanate(s) selected from the group consisting of:
(i) isocyanate represented by the following general formula:
CH.sub.2 .dbd.C(Y)--C(O)OR'--N.dbd.C.dbd.O
wherein Y is selected from the group consisting of hydrogen and C.sub.1 -C.sub.5 alkyl;
and R' is a C.sub.1 -C.sub.20 alekylene or phenylene;
(ii) m-isopropenyl-.alpha., .alpha.-dimethyl benzyl isocyanate;
(iii) product of the reaction of acrylic functional monomer(s) containing a vinyl ether group and isocyanic acid;
(iv) product of the reaction of unsaturated monomer(s) having a functional group selected from the group consisting of amino, hydroxy, thio and a combination of said functional groups and isocyanate(s) having at least two functional isocyanate groups;
and
(v) mixtures of these isocyanates;
and
c. curing the applied polymerizable composition.

10 more elements

Dependencies are inferred from the claim text.