Methods for preparing optical articles and optical articles prepared therefrom

• US 10,012,773 B2
• Filed: 02/10/2017
• Issued: 07/03/2018
• Est. Priority Date: 12/13/2012
• Status: Active Grant

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Bojkova, Nina Vassileva, Graham, Marvin Jerome, Kryger, Matthew J., Menta, Federico
• Primary Examiner(s): Sergent, Rabon
• Application Number:
  US15/429,330
• Publication Number:
  US 20170153359A1
• Time in Patent Office: 508 Days
• CPC Class Codes: B29C 45/0001 characterised by the choice of material
• CPC Class Codes: B29C 45/72 Heating or cooling
• CPC Class Codes: B29D 11/00009 Production of simple or compound lenses
• CPC Class Codes: B29K 2995/0026 Transparent
• CPC Class Codes: B29K 2995/0031 Refractive
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/3203 Polyhydroxy compounds
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08G 18/3212 containing cycloaliphatic groups
• CPC Class Codes: C08G 18/3215 containing aromatic groups or benzoquinone groups
• CPC Class Codes: C08G 18/3271 Hydroxyamines
• CPC Class Codes: C08G 18/3275 containing two hydroxy groups
• CPC Class Codes: C08G 18/34 Carboxylic acids; Esters thereof with monohydroxyl compounds
• CPC Class Codes: C08G 18/3876 containing mercapto groups
• CPC Class Codes: C08G 18/4825 Polyethers containing two hydroxy groups C08G18/4833 - C08G18/5096 take precedence
• CPC Class Codes: C08G 18/6685 with compounds of group C08G18/3225 or polyamines of C08G18/38
• CPC Class Codes: C08G 18/6688 with compounds of group C08G18/3271
• CPC Class Codes: C08G 18/721 Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
• CPC Class Codes: C08G 18/722 Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
• CPC Class Codes: C08G 18/724 : Combination of aromatic polyisocyanates with (cyclo)aliphatic polyisocyanates
• CPC Class Codes: C08G 18/73 : acyclic
• CPC Class Codes: C08G 18/755 : and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/758 : containing two or more cycloaliphatic rings
• CPC Class Codes: C08G 2120/00 : Compositions for reaction injection moulding processes
• CPC Class Codes: C08L 75/02 : Polyureas
• CPC Class Codes: C08L 75/04 : Polyurethanes
• CPC Class Codes: C08L 81/00 : 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 Class Codes: G02B 1/04 : made of organic materials, e.g. plastics G02B1/08 takes precedence
• CPC Class Codes: G02B 1/041 : Lenses
• CPC Class Codes: G02B 1/08 : made of polarising materials
• CPC Class Codes: G02B 1/14 : Protective coatings, e.g. hard coatings

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.

Claims

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 H₂N-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:

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.

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.

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 H₂N-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.

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 H₂N-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 second reaction mixture onto a support substrate to form a film thereon; and

(5) heating the film on the support substrate to a temperature and for a time sufficient to form a cured, non-elastomeric polyurethane-containing film having a uniform thickness.

18. A cured, non-elastomeric polyurethane-containing film prepared by the method of claim 17.

19. A polarizing optical element comprising the cured, non-elastomeric polyurethane-containing film of claim 18.