Methods for preparing optical articles and optical articles prepared therefrom

Patent metadata

Field	Value
Publication number	US-10012773-B2
Application number	US-201715429330-A
Country	US
Kind code	B2
Filing date	Feb 10, 2017
Priority date	Dec 13, 2012
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

Provided is a method of preparing a transparent, non-elastomeric optical article including (1) combining to form a reaction mixture free of urethanation catalysts (a) a polyisocyanate component; and (b) an active hydrogen component of polyol and/or polythiol, and at least one compound containing both amine and hydroxyl functional groups; (2) allowing the polyisocyanate component to react with amine functional groups in the active hydrogen component to form an intermediate product including a polyurea prepolymer having hydroxyl functional groups in admixture with the polyol and/or polythiol and, optionally, the compound containing both amine and hydroxyl functional groups; (3) mixing the intermediate product with additional polyisocyanates and optionally a urethanation catalyst to form a second reaction mixture; (4) introducing the second reaction mixture to a mold to form a thermoset polymerizate; and (5) releasing the polymerizate from the mold. Optical films and articles prepared by the method also are provided.

First claim

The invention claimed is:

1. A method of preparing a transparent, non-elastomeric optical article comprising:
(1) combining to form a reaction mixture that is free of urethanation catalysts:
(a) a polyisocyanate component comprising one or more different polyisocyanates; and
(b) an active hydrogen component comprising:
(b)(i) at least one polyol and/or polythiol, and
(b)(ii) at least one compound containing both an amine functional group and a hydroxyl functional group and having the structure H 2 N-L-OH, wherein L is a linear or branched alkyl, aryl, aralkyl, or alkaryl chain which, optionally, contains hetero atoms;

(2) allowing the polyisocyanate component (a) to react with amine functional groups in the active hydrogen component (b) at a temperature and for a time sufficient to form an intermediate product comprising a polyurea prepolymer having hydroxyl functional groups in admixture with the polyol and/or polythiol (b)(i), and, optionally, the compound (b)(ii) which contains both an amine functional group and a hydroxyl functional group;
(3) mixing the intermediate product formed in step (2) with additional polyisocyanates and, optionally, a urethanation catalyst to form a second reaction mixture;
(4) introducing the second reaction mixture formed in step (3) 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.

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

3. The method of claim 1 , wherein the equivalent ratio of amine functional groups to isocyanate functional groups in the reaction mixture formed in step (1) is at least 1.

4. The method of claim 1 , wherein the compound (b)(ii) which contains both an amine functional group and a hydroxyl functional group has a number average molecular weight of 60 to 450.

5. The method of claim 1 , wherein the compound (b)(ii) which contains both an amine functional group and a hydroxyl functional group 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.

6. The method of claim 1 , wherein the compound (b)(ii) which contains both an amine functional group and a hydroxyl functional group comprises ethanolamine, amino-2-propanol, 2-amino-1-methyl-1-propanol, 2-amino-1-butanol and/or diethylene glycolamine.

7. The method of claim 6 , wherein the compound (b)(ii) which contains both an amine functional group and a hydroxyl functional group is present in the active hydrogen component (b) in an amount of 5 to 70 percent by weight, based on the total weight of resin solids in component (b).

8. The method of claim 1 , wherein the catalyst added in step (3) comprises phosphines, stannous octoate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin mercaptide, dibutyl tin dimaleate, dimethyl tin diacetate, dimethyl tin oxide, dibutyltin dichloride, 1,4-diazabicyclo[2.2.2]octane, zinc octoate, bismuth, ferric acetylacetonate, triethylamine, triisopropylamine, dimethyl cyclohexylamine, N,N-dimethylbenzylamine or mixtures thereof.

9. The method of claim 1 , wherein (b)(i) comprises at least two different polyols and/or polythiols, and (b)(ii) comprises at least one compound containing both an amine functional group and a hydroxyl functional group, wherein the amine and hydroxyl functional groups on the compound (b)(ii) are not directly bonded to aromatic rings.

10. The method of claim 9 , wherein at least one of the polyols is an aromatic ring-containing polyol wherein hydroxyl groups in the polyol are not directly bonded to the aromatic ring.

11. The method of claim 1 , wherein the transparent optical article demonstrates a refractive index of at least 1.52.

12. The method of claim 1 , wherein the reaction mixture is free of polyamines and free of compounds containing both amino and aromatic groups where the amino groups are attached directly to the aromatic ring.

13. A method of preparing a transparent, non-elastomeric optical article comprising:
(1) combining to form a reaction mixture that is free of urethanation catalysts:
(a) a polyisocyanate component comprising one or more different polyisocyanates; and
(b) an active hydrogen component comprising:
(b)(i) at least one polyol and/or polythiol, and
(b)(ii) at least one compound containing both an amine functional group and a hydroxyl functional group, said compound having the structure H 2 N-L-OH, wherein L is a linear or branched alkyl, aryl, aralkyl, or alkaryl chain which, optionally, contains hetero atoms, wherein said compound is present in stoichiometric excess with respect to amine groups relative to isocyanate functional groups;

(2) allowing the polyisocyanate component (a) to react with at least a portion of the amine functional groups in the active hydrogen component (b) at a temperature and for a time sufficient to consume essentially all of the isocyanate functional groups and form an intermediate product comprising a polyurea prepolymer having hydroxyl functional groups in admixture with the polyol and/or polythiol (b)(i), and the compound (b)(ii) which contains both an amine functional group and a hydroxyl functional group;
(3) mixing the intermediate product formed in step (2) with additional polyisocyanates and a urethanation catalyst to form a second reaction mixture;
(4) introducing the second reaction mixture formed in step (3) 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.

14. A transparent, non-elastomeric optical article prepared by the method of claim 1 .

15. The optical article of claim 14 , 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 14 , wherein the article is a polarizing optical element.

17. A method for preparing a cured, non-elastomeric polyurethane-containing film comprising:
(1) combining to form a reaction mixture that is free of urethanation catalysts:
(a) a polyisocyanate component comprising one or more different polyisocyanates; and
(b) an active hydrogen component comprising:
(b)(i) at least one polyol and/or polythiol, and
(b)(ii) at least one compound containing both an amine functional group and a hydroxyl functional group and having the structure H 2 N-L-OH, wherein L is a linear or branched alkyl, aryl, aralkyl, or alkaryl chain which, optionally, contains hetero atoms;

(2) allowing the polyisocyanate component (a) to react with amine functional groups in the active hydrogen component (b) at a temperature and for a time sufficient to form an intermediate product comprising a polyurea prepolymer having hydroxyl functional groups in admixture with the polyol and/or polythiol (b)(i) and, optionally, the compound (b)(ii) which contains both an amine functional group and a hydroxyl functional group;
(3) mixing the intermediate product formed in step (2) with additional polyisocyanates and, optionally, a urethanation catalyst to form a second reaction mixture;
(4) dispensing the se

Assignees

• Ppg Ind Ohio Inc

Inventors

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

Classifications

• C08G18/758

  containing two or more cycloaliphatic rings · CPC title

• C08G18/6688

  with compounds of group C08G18/3271 · CPC title

• B29K2995/0026

  Transparent · CPC title

• C08L81/00

  Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers · CPC title

• B29K2995/0031

  Refractive · CPC title