Optical articles and methods for preparation of same

Patent metadata

Field	Value
Publication number	US-9891349-B2
Application number	US-201715429352-A
Country	US
Kind code	B2
Filing date	Feb 10, 2017
Priority date	Dec 13, 2012
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

Provided is a transparent, non-elastomeric optical article prepared by (1) combining to form a reaction mixture (a) a polyisocyanate component; and (b) an active hydrogen component including (b1) a first component free of amino groups including at least one first polyol; and (b2) a second component containing (i) a second polyol and/or a polythiol and (ii) a compound containing both amine and hydroxyl functional groups; (2) introducing the reaction mixture to a mold at a temperature and for a time sufficient to form a thermoset polymerizate; and (3) releasing the polymerizate from the mold to yield a transparent, non-elastomeric optical article. Also provided is a method for preparing a transparent optical film. Optical films and articles prepared by the methods also are provided.

First claim

The invention claimed is:

1. A transparent, non-elastomeric optical article prepared by the method comprising:
(1) combining to form a reaction mixture:
(a) a polyisocyanate component comprising one or more different polyisocyanates; and
(b) an active hydrogen component comprising:
(b1) a first component that is free of amino groups comprising at least one first polyol; and
(b2) a second component comprising (i) at least one second polyol and/or at least one polythiol and (ii) at least one compound containing both amine and hydroxyl functional groups which has the structure H 2 N-L-OH, wherein L is a linear or branched alkyl, aryl, aralkyl, or alkaryl chain optionally containing hetero atoms, wherein the at least one second polyol has a number average molecular weight of 60 to 450;
(2) introducing the reaction mixture to a mold at a temperature and for a time sufficient to form a thermoset polymerizate; and
(3) releasing the polymerizate from the mold to yield a transparent, non-elastomeric optical article.

2. The optical article of claim 1 , wherein less than 40 percent by weight of the first polyols based on total weight of first polyols in the first component (b1) have a number average molecular weight greater than 450.

3. The optical article of claim 2 , wherein less than 35 percent by weight of the first polyols based on total weight of first polyols in the first component (b1) have a number average molecular weight greater than 450.

4. The optical article of claim 3 , wherein less than 30 percent by weight of the first polyols based on total weight of first polyols in the first component (b1) have a number average molecular weight greater than 450.

5. The optical article of claim 1 , wherein the polyisocyanate component comprises isophorone diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, diphenylmethane-4,4′-diisocyanate, (1,3-bis(1-isocyanato-1-methylethyl)-benzene), and/or meta-xylylene diisocyanate.

6. The optical article of claim 1 , wherein the compound containing both amine and hydroxyl functional groups has a number average molecular weight of 60 to 450.

7. The optical article of claim 1 , wherein the compound containing both amine and hydroxyl functional groups has the structure:

wherein R is H or a C 1 to C 4 alkyl group and n is an integer from 1 to 10.

8. The optical article of claim 1 , wherein the compound containing both amine and hydroxyl functional groups comprises ethanolamine, amino-2-propanol, 2-amino-1-methyl-1-propanol, 2-amino-1-butanol, and/or diethylene glycolamine.

9. The optical article of claim 1 , wherein the reaction mixture is free of polyamines.

10. The optical article of claim 1 , wherein the reaction mixture is free of compounds containing both amino and aromatic functional groups.

11. The optical article of claim 1 , wherein the reaction mixture is free of polyols containing hydroxyl groups directly attached to aromatic rings.

12. The optical article of claim 1 , wherein (b2) of the active hydrogen component (b) comprises at least one polythiol.

13. The optical article of claim 1 , which demonstrates a refractive index of at least 1.52.

14. A transparent, non-elastomeric optical article prepared by the method comprising:
(1) combining to form a reaction mixture:
(a) a polyisocyanate component comprising one or more different polyisocyanates; and
(b) at least one first polyol, wherein the polyisocyanate component is present in stoichiometric excess relative to hydroxyl functional groups;
(2) allowing the components to react at a temperature and for a time sufficient to consume all of the hydroxyl functional groups and form an intermediate product comprising a polyurethane prepolymer having isocyanate functional groups in admixture with excess polyisocyanate;
(3) mixing the intermediate product formed in step (2) with
at least one compound containing both amine and hydroxyl functional groups wherein the compound containing both amine and hydroxyl functional groups has the structure H 2 N-L-OH, wherein L is a linear or branched alkyl, aryl, aralkyl, or alkaryl chain optionally containing hetero atoms to form a second reaction mixture, and
optionally an active hydrogen component comprising at least one second polyol and/or at least one polythiol;
(4) introducing the second reaction mixture formed in step (3) via injection to a mold at a temperature and for a time sufficient to form a thermoset polymerizate; and
(5) releasing the polymerizate from the mold to yield a transparent optical article.

15. The optical article of claim 1 , which is selected from the group consisting of camera lenses, ophthalmic articles, ocular devices, sun lenses, fashion lenses, sport masks, face shields, goggles, glazings, and transparencies.

16. The optical article of claim 1 , which is a polarizing optical element.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Bojkova Nina Vassileva
• Graham Marvin Jerome
• Kryger Matthew J
• Menta Federico

Classifications

• G02B1/04 Primary

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• C08L75/02

  Polyureas · CPC title

• B29C45/72

  Heating or cooling · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C08G18/3215

  containing aromatic groups or benzoquinone groups · CPC title