US 2014/0155572 A1 · EPOXIDE AND THIOEPOXIDE FUNCTIONAL, POLYMERIZABLE COMPOSITIONS AND METHODS OF PREPARING OPTICAL ARTICLES THEREFROM

Abstract

Provided is a thioepoxide functional polymerizable composition comprising a reaction product of thiourea and an epoxide functional, polymerizable composition. The epoxide functional, polymerizable composition comprises a reaction product prepared from a reaction mixture comprising: (a) a monomer comprising at least one ethylenically unsaturated ester functional monomer having an epoxide functional group; and (b) a compound having two or more thiol groups. The reactants (a) and (b) are reacted via a Michael addition reaction in the presence of a base to form an epoxide functional reaction product. Also provided are methods of preparing an optical article using the polymerizable compositions.

Claims17

Dependent claims

A thioepoxide functional, polymerizable composition comprising a reaction product of:

(a) thiourea;
and
(b) an epoxide functional, polymerizable composition comprising a reaction product prepared from a reaction mixture comprising:
(i) a monomer comprising at least one ethylenically unsaturated ester functional monomer having an epoxide functional group;
and
(ii) a compound having two or more thiol groups;
wherein the reactants (i) and (ii) are reacted via a Michael addition reaction in the presence of a base to form an epoxide functional reaction product.

4 more elements

A method of preparing an optical article comprising:

(1) reacting together:
(a) a monomer comprising at least one ethylenically unsaturated ester functional monomer having an epoxide functional group;
and
(b) a compound having two or more thiol groups;
wherein the reactants (a) and (b) are reacted via a Michael addition reaction in the presence of a base to form an epoxide functional reaction product;
(2) reacting the epoxide functional reaction product formed in step (1) with thiourea to form a thioepoxide functional, polymerizable composition;
(3) mixing the thioepoxide functional, polymerizable composition formed in step (2) with:
(a) a polymerizable composition comprising at least one ethylenically unsaturated (meth)acrylate functional monomer having a thioepoxide functional group;
(b) an addition polymerization initiator;
and
(c) a catalyst to form a reaction mixture;
(4) introducing the reaction mixture formed in step (3) to a mold of a desired shape at a temperature and for a time sufficient to form a polymerizate;
and
(5) releasing the polymerizate from the mold to yield an optical article.

11 more elements

A method of preparing an optical article comprising:

(1) reacting together reactants:
(a) a monomer comprising at least one ethylenically unsaturated ester functional monomer having an epoxide functional group;
and
(b) a compound having two or more thiol groups;
wherein the monomer (a) is present in stoichiometric excess and the reactants (a) and (b) are reacted via a Michael addition reaction in the presence of a base to form a product mixture comprising an epoxide functional reaction product and excess monomer (a);
(2) reacting the product mixture formed in step (1) with thiourea to form a thioepoxide functional, polymerizable composition;
(3) preparing a prepolymer reactant mixture by:
(i) mixing the thioepoxide functional, polymerizable composition formed in step (2) with:
(a) a first polymerizable composition comprising at least one ethylenically unsaturated monomer;
and
(b) an azo addition polymerization initiator to form a reaction mixture;
and
(ii) allowing ethylenically unsaturated groups in the reaction mixture formed in (i) to polymerize to form a prepolymer having a threshold viscosity of 50 to 500 centipoise measured at 25° C., wherein the azo addition polymerization initiator is present in an amount sufficient only to achieve the threshold viscosity;
(4) mixing the prepolymer reactant mixture formed in step (3) with:
(a) an initiator package that is essentially free of azo initiators;
and
(b) a second polymerizable composition comprising at least one ethylenically unsaturated monomer having two or more ethylenically unsaturated groups to form a moldable composition;
(5) introducing the moldable composition formed in step (4) to a mold of a desired shape at a temperature and for a time sufficient to form a polymerizate;
(6) releasing the polymerizate from the mold to yield an optical article.

16 more elements

Dependencies are inferred from the claim text.

Facts

Application

13/961,443Filed 7 Aug 2013

Priority

5 Dec 2012

Published

5 Jun 2014

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

C08F 220/382
Esters containing sulfur: and containing oxygen, e.g. 2-sulfoethyl acrylate
C07D 331/02
Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom: three-membered rings
C08G 75/045
From mercapto compounds or metallic derivatives thereof: from mercapto compounds and unsaturated compounds
G02B 1/04
Optical elements characterised by the material of which they are made; Optical coatings for optical elements: made of organic materials, e.g. plastics

Epoxide and thioepoxide functional, polymerizable compositions and methods of preparing optical articles therefrom

Life of this patent

Epoxide and thioepoxide functional, polymerizable compositions and methods of preparing optical articles therefrom

Life of this patent

Abstract

Claims17