Abstract: A batch process for preparing a molded optical article includes introducing (i) a dithiol component or (ii) a polyisocyanate component into a reaction vessel; adding a first catalyst of organotin halide to form a first reaction mixture; heating the first reaction mixture; introducing a second catalyst of tertiary amine to the first reaction mixture; mixing a polyisocyanate (ii) into the reaction vessel containing the first reaction mixture if dithiol (i) was first added, or mixing a dithiol (i) into the first reaction mixture if the polyisocyanate (ii) was first added, to form a second reaction mixture; filling a mold with the second reaction mixture to provide a filled mold to form a molded optical article. The molar ratio of elemental tin present in the first catalyst to tertiary amine compound present in the second catalyst ranges from 0.04:1 to 0.29:1.

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.

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.

Abstract: Provided is a polymerizable composition including (meth)acrylate monomers having at least two sulfide (—S—) linkages in the monomer. The polymerizable compositions include a first (meth)acrylate monomer represented by the following Formula (I), where L1 is selected from a multivalent optionally substituted hydrocarbyl group optionally interrupted with at least one of —C(O)—, —S—, —O— and combinations thereof, and a divalent linking group represented by the following Formula (A). In Formula (A), Y is O or S. Also in Formula (I), L2 is independently for each n a divalent optionally substituted hydrocarbyl group optionally interrupted with at least one of —O— and —S—, R1 is independently selected for each n from hydrogen and methyl, and n is from 2 to 6. The polymerizable compositions also may include a polymerization moderator. Also provided are polymerizates including photochromic articles and optical elements prepared from such polymerizable compositions.

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.

Abstract: Provided is a polymerizable composition of (a) a monomer composition including ethylenically unsaturated monomer having a ?-epithiopropyl functional group; (b) optionally, a compound having two or more ?-epithiopropyl functional groups but no polymerizable ethylenically unsaturated groups; (c) an isourea functional polymerization initiator; and (d) a catalyst for reaction between the ?-epithiopropyl functional groups. Also provided is a method of reducing the yellowness index of a sulfur-containing polymerizate prepared by addition polymerization, the method including reacting in the presence of an isourea functional polymerization initiator and a catalyst for reaction between ?-epithiopropyl functional groups, a polymerizable composition of: (a) a monomer composition including ethylenically unsaturated monomer having a ?-epithiopropyl functional group; and, optionally, (b) a compound having two or more ?-epithiopropyl functional groups but no polymerizable ethylenically unsaturated groups.

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.

Abstract: Provided is a polymerizable composition of (a) a monomer composition including ethylenically unsaturated monomer having a ?-epithiopropyl functional group; (b) optionally, a compound having two or more ?-epithiopropyl functional groups but no polymerizable ethylenically unsaturated groups; (c) an isourea functional polymerization initiator; and (d) a catalyst for reaction between the ?-epithiopropyl functional groups. Also provided is a method of reducing the yellowness index of a sulfur-containing polymerizate prepared by addition polymerization, the method including reacting in the presence of an isourea functional polymerization initiator and a catalyst for reaction between ?-epithiopropyl functional groups, a polymerizable composition of: (a) a monomer composition including ethylenically unsaturated monomer having a ?-epithiopropyl functional group; and, optionally, (b) a compound having two or more ?-epithiopropyl functional groups but no polymerizable ethylenically unsaturated groups.

Abstract: Provided is a polymerizable composition including (meth)acrylate monomers having at least two sulfide (—S—) linkages in the monomer. The polymerizable compositions include a first (meth)acrylate monomer represented by the following Formula (I), where L1 is selected from a multivalent optionally substituted hydrocarbyl group optionally interrupted with at least one of —C(O)—, —S—, —O— and combinations thereof, and a divalent linking group represented by the following Formula (A). In Formula (A), Y is O or S. Also in Formula (I), L2 is independently for each n a divalent optionally substituted hydrocarbyl group optionally interrupted with at least one of —O— and —S—, R1 is independently selected for each n from hydrogen and methyl, and n is from 2 to 6. The polymerizable compositions also may include a polymerization moderator. Also provided are polymerizates including photochromic articles and optical elements prepared from such polymerizable compositions.

Abstract: Provided is a process for preparing a molded optical article that is essentially free of optical defects. The process comprises: a) introducing each of two separate reactive components A and B from separate supply vessels into a mixing chamber having a volume of 200 ml to 2000 ml; b) mixing the components together in the mixing chamber for a period of 50 to 200 seconds to form a reaction mixture; c) injecting the reaction mixture at a temperature of up to 130° C. into a mold; d) holding the reaction mixture in the mold at a temperature and for a time sufficient to essentially cure the reaction mixture and form a molded optical article; and e) releasing the article from the mold. The process is particularly suitable for preparing polythiourethane lenses with high yield, high transparency, very low haze, low flow lines and low inclusions.

Abstract: The present invention provides polythiol oligomer formed by the reaction of at least two or more different dienes and at least one or more dithiol wherein stoichiometric ratio of the sum of the number of equivalents of all polythiols to the sum of the number of equivalents of all dienes used to form the polythiol oligomer is greater than 1.0:1.0; and wherein the two or more different dienes comprise (a) at least one non-cyclic diene and at least one cyclic diene; or (b) at least one aromatic ring-containing diene and at least one non-aromatic cyclic diene; or (c) at least one non-aromatic monocyclic diene and at least one non-aromatic polycyclic diene; Sulfur-containing polyurethane of the present invention can be prepared by combining polyisocyanate, polyisothiocyanate, or mixture thereof; the polythiol oligomer described above; and active hydrogen-containing material.

Abstract: Sealant and potting formulations comprising a thioether-functional, oligomeric polythiol prepared by reacting together: (a) a compound having at least two thiol functional groups; and (b) a compound having triple bond functionality are disclosed.

Abstract: Provided is a composition including a reaction product of: (A) a reactive compound that includes a material having functional groups that are reactive with active hydrogens; (B) a thioether-functional, oligomeric polythiol prepared by reacting together: (1) a compound having at least two thiol functional groups; (2) a compound having triple bond functionality; and optionally (3) a compound having at least two double bonds; and, optionally, (C) a compound different from (B) containing active hydrogens. Coating compositions, articles of manufacture and related processes also are provided.

Abstract: Provided is a thioether-functional, oligomeric polythiol having pendant hydroxyl functional groups, prepared by reacting together: (a) a compound having at least two thiol functional groups; and (b) a hydroxyl functional compound having triple bond functionality. Also provided are optical articles prepared from the reaction product of: (A) a reactive compound having functional groups that are reactive with active hydrogens; (B) a thioether-functional, oligomeric polythiol; and, optionally, (C) a compound different from (B) containing active hydrogens.

Abstract: The present invention relates to a sulfur-containing polyureaurethane and a method of preparing the polyureaurethane. The sulfur-containing polyureaurethane has a refractive index of at least 1.57, an Abbe number of at least 32 and a density of less than 1.3 grams/cm3 when cured. The sulfur-containing polyureaurethane is prepared by the reaction of: (a) a sulfur-containing, isocyanate functional polyurethane prepolymer derived from: (i) a polyisocyanate; and (ii) a polythiol oligomer produced by the reaction of at least two or more different dienes with one or more dithiols and in certain embodiments at least one trifunctional or higher-functional polythiol; and (b) an amine-containing curing agent.

Abstract: Provided is a thioether-functional, oligomeric polythiol having pendant hydroxyl functional groups, prepared by reacting together: (a) a compound having at least two thiol functional groups; (b) a hydroxyl functional compound having triple bond functionality; and (c) a compound having at least two double bonds. Further provided is a thioether-functional, oligomeric polythiol having pendant hydroxyl functional groups, prepared by reacting together: (a) a compound having at least two thiol functional groups, prepared by reacting together: (1) a dithiol, and (2) a compound having at least two double bonds; (b) a hydroxyl functional compound having triple bond functionality; and optionally (c) an additional compound having at least two double bonds, which may be the same as or different from the compound (2). Optical articles prepared from the thioether-functional, oligomeric polythiols are also provided.

Abstract: The present invention relates to sulfide-containing polythiols and their methods of preparation. Sulfide-containing polythiols can have a variety of uses and applications. The sulfide-containing polythiols of the present invention can be especially useful in polyurethane compositions for the manufacture of ophthalmic lenses.

Abstract: Provided is a thioether-functional, oligomeric polythiol having pendant hydroxyl functional groups, prepared by reacting together: (a) a compound having at least two thiol functional groups; (b) a hydroxyl functional compound having triple bond functionality; and (c) a compound having at least two double bonds. Further provided is a thioether-functional, oligomeric polythiol having pendant hydroxyl functional groups, prepared by reacting together: (a) a compound having at least two thiol functional groups, prepared by reacting together: (1) a dithiol, and (2) a compound having at least two double bonds; (b) a hydroxyl functional compound having triple bond functionality; and optionally (c) an additional compound having at least two double bonds, which may be the same as or different from the compound (2). Optical articles prepared from the thioether-functional, oligomeric polythiols are also provided.

Abstract: Provided is a thioether-functional, oligomeric polythiol having pendant hydroxyl functional groups, prepared by reacting together: (a) a compound having at least two thiol functional groups; and (b) a hydroxyl functional compound having triple bond functionality. Also provided are optical articles prepared from the reaction product of: (A) a reactive compound having functional groups that are reactive with active hydrogens; (B) a thioether-functional, oligomeric polythiol; and, optionally, (C) a compound different from (B) containing active hydrogens.

Abstract: The present invention relates to a sulfur-containing polyureaurethane and a method of preparing said polyureaurethane. In an embodiment, the sulfur-containing polyureaurethane when at least partially cured can have a refractive index of at least 1.57, an Abbe number of at least 35 and a density of less than 1.3 grams/cm3. Further, the sulfur-containing polyureaurethane can be prepared by reacting a polyureaurethane prepolymer comprising a polycyanate and at least one hydrogen-containing material, at least one episulfide-containing material; and an amine-containing curing agent.