Optical material comprising a red-shifted benzotriazole UV absorber

Patent metadata

Field	Value
Publication number	US-10838111-B2
Application number	US-201716095556-A
Country	US
Kind code	B2
Filing date	Apr 21, 2017
Priority date	Apr 21, 2016
Publication date	Nov 17, 2020
Grant date	Nov 17, 2020

Abstract

The present invention relates to an eyeglass lens comprising a substrate made of an optical material comprising a polymer matrix and at least one 2-(2-hydroxy-5-R 1 -phenyl)benzotriazole, in which R 1 is a resonant group, the optical transmittance through a 2 mm thick layer of said optical material being lower than 1% for each light wavelength ranging from 280 to 405 nm. This eyeglass lens protects from phototoxic blue light and UV light.

First claim

The invention claimed is:

1. An eyeglass lens comprising a substrate made of an optical material comprising a polymer matrix and at least one 2-(2-hydroxy-5-R 1 -phenyl)benzotriazole, in which F 1 is a resonant group, wherein optical transmittance through a 2 mm thick layer of said optical material is lower than 1% for each light wavelength ranging from 280 to 405 nm.

2. The eyeglass lens of claim 1 , wherein said at least one 2-(2-hydroxy-5-R 1 -phenyl)benzotriazole does not comprise any polymerizable group selected from allylic, acrylic and methacrylic moieties.

3. The eyeglass lens of claim 1 , wherein said benzotriazole is a compound of formula (I):

in which R 1 is a resonant group, the R 2 groups are identical or different monovalent groups, n is an integer equal to 0 or 1, the R 3 groups are identical or different monovalent groups, m is an integer ranging from 0 to 2.

4. The eyeglass lens of claim 3 , wherein m=0.

5. The eyeglass lens of claim 1 , wherein R 1 is selected from the groups amino, hydroxyl, alkoxy, aryloxy, alkylamino, arylamino, dialkylamino, diarylamino, (aryl)(alkyl)amino, formamido, alkylamido, arylamido, formyloxy, alkylcarboxy, arylcarboxy, alkylimino, and arylimino.

6. The eyeglass lens of claim 5 , wherein R 1 is selected from the groups amino, hydroxyl, alkoxy, aryloxy, alkylamino, arylamino, dialkylamino, diarylamino, and (aryl)(alkyl)amino.

7. The eyeglass lens of claim 1 , wherein the R 1 and R 3 groups are independently selected from a hydrogen atom and linear or branched, substituted or unsubstituted hydrocarbon groups comprising from 1 to 6 carbon atoms.

8. The eyeglass lens of claim 1 , wherein 2-(2-hydroxy-5-R 1 -phenyl)benzotriazole, in which R 1 is a resonant group, are present in an amount ranging from 0.05 to 3.0% by weight relative to the total weight of the substrate.

9. The eyeglass lens of claim 1 , wherein the polymer matrix comprises at least one of a polyurethane, polythiourethane, polyepisulfide, polymer obtained from a polyol allyl carbonate, polycarbonate, or poly(meth)acrylate.

10. The eyeglass lens of claim 9 , wherein the polymer matrix comprises at least one polymer obtained from diethylene glycol bis(allyl carbonate) or ethylene glycol bis(allyl carbonate).

11. The eyeglass lens of claim 9 , wherein the polymer matrix comprises at least one polymer obtained from copolymerization of at least one polyisocyanate and at least one polythiol or from copolymerization of at least one polyepisulfide and at least one polythiol.

12. The eyeglass lens of claim 1 , wherein the optical transmittance through a 2 mm thick layer of said optical material is lower than 1% for each light wavelength ranging from 280 to 410 nm.

13. A method for preparing an eyeglass lens of claim 1 , comprising:
obtaining a polymerizable composition comprising at least one 2-(2-hydroxy-5-R 1 -phenyl)benzotriazole, in which R 1 is a resonant group, and at least one polymerizable compound; and
curing said polymerizable composition so as to form a substrate made of an optical material comprising a polymer matrix and said at least one 2-(2-hydroxy-5-R 1 -phenyl)benzotriazole;

wherein the optical transmittance through a 2 mm thick layer of said optical material is lower than 1% for each light wavelength ranging from 280 to 405 nm.

14. The method of claim 13 , wherein said at least one polymerizable compound is selected from polyol allyl carbonates, polythiols, episulfides, polyisocyanates, polyisothiocyanates and (meth)acrylates.

15. The method of claim 14 , wherein the polymer matrix comprises at least one polymer obtained from diethylene glycol bis(allyl carbonate), ethylene glycol bis(allyl carbonate), from at least one polyisocyanate and at least one polythiol or from at least one polyepisulfide and at least one polythiol.

Assignees

• Essilor Int

Inventors

• Fromentin Pierre

Classifications

• C07D249/20

  with aryl radicals directly attached in position 2 · CPC title

• C08L69/00

  Compositions of polycarbonates; Compositions of derivatives of polycarbonates · CPC title

• C08G18/52

  Polythioethers · CPC title

• C08G18/72

  Polyisocyanates or polyisothiocyanates · CPC title

• G02B1/041 Primary

  Lenses · CPC title