Ophthalmic lens comprising an oxazolone

Patent metadata

Field	Value
Publication number	US-12282138-B2
Application number	US-201917312469-A
Country	US
Kind code	B2
Filing date	Dec 11, 2019
Priority date	Dec 13, 2018
Publication date	Apr 22, 2025
Grant date	Apr 22, 2025

Abstract

The present invention relates to ophthalmic lenses comprising an oxazolone, a preparation method thereof and the use of an oxazolone in an ophthalmic lens to absorb blue light.

First claim

The invention claimed is:

1. An ophthalmic lens comprising:
a plastic base; and
an oxazolone,

wherein the oxazolone is represented by formula (I):

wherein
A is a 5-membered ring selected from one of the following:

each R 1 is independently selected from the group consisting of halogen, (C 1-6 )alkyl, (C 1-6 )haloalkyl, —OH, —OR, —NH 2 , —NH((C 1-6 )alkyl), —N((C 1-6 )alkyl) 2 , —NO 2 , —CN, —NH—C(O)—(C 1-6 )alkyl and —O—C(O—(C 1-6 )alkyl;
each R 2 is independently selected from the group consisting of halogen, (C 1-6 )alkyl, (C 1-6 )haloalkyl, —OH, —OR, —NH 2 , —NH((C 1-6 )alkyl), —N((C 1-6 )alkyl) 2 , —NO 2 , —CN, —NH—C(O)—(C 1-6 )alkyl and —O—C(O—(C 1-6 )alkyl;
R is (C 1-6 )alkyl or (C 1-6 )haloalkyl;
n is 0, 1, 2, 3, 4 or 5; and
m is 0, 1, 2, 3, 4 or 5.

2. The ophthalmic lens of claim 1 , wherein each R 1 is independently selected from the group consisting of Cl, Br, F, —CF 3 , —OH, —OCH 3 , —NH 2 , —N(CH 3 ) 2 , —CH 3 , —C 2 H 5 , —NO 2 , —CN, and —O—C(O)—CH 3 .

3. The ophthalmic lens of claim 1 , wherein each R 2 is independently selected from the group consisting of Cl, Br, F, —CF 3 , —OH, —OCH 3 , —NH 2 , —N(CH 3 ) 2 , —CH 3 , —C 2 H 5 , —NO 2 , —CN, and —O—C(O)—CH 3 .

4. The ophthalmic lens of claim 1 , wherein the oxazolone is represented by formula (II) or (III):

wherein R 1 , R 2 , n and m are as defined in claim 1 .

5. The ophthalmic lens of claim 1 , wherein:
each R 2 is independently selected from the group consisting of Cl, F, —CF 3 , NO 2 ,—OH and —OCH 3 ;
n is 0; and
m is 0, 1 or 2.

6. The ophthalmic lens of claim 5 , wherein each R 2 is independently selected from the group consisting of Cl, F and CF 3 .

7. The ophthalmic lens of claim 1 , wherein the oxazolone is represented by one of the following formula (IVa)-(IVk):

8. The ophthalmic lens of claim 1 , wherein the stereochemistry of the carbon-carbon double bond in the oxazolone is (Z).

9. The ophthalmic lens of claim 1 , wherein the oxazolone has a maximum absorption wavelength (λmax) lower than 400 nm, as measured on a 10 ppm solution of oxazolone in ethanol.

10. The ophthalmic lens of claim 1 , wherein the oxazolone is included in the plastic base or is included in a separate layer coated on a surface of the plastic base.

11. The ophthalmic lens of claim 1 , wherein the oxazolone is encapsulated within nanoparticles.

12. The ophthalmic lens of claim 1 , wherein the amount of oxazolone is 0.001 to 5% by weight based on the weight of the plastic base when the oxazolone is included in the plastic base or on the weight of a separate layer when the oxazolone is included in a separate layer coated on a surface of the plastic base.

13. The ophthalmic lens of claim 1 , wherein the ophthalmic lens further comprises a benzotriazole UV-absorber or a mixture thereof.

14. The ophthalmic lens of claim 13 , wherein the benzotriazole UV-absorber is selected from the group consisting of 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole, and mixtures thereof.

15. The ophthalmic lens of claim 13 , wherein the total amount of benzotriazole UV-absorber is 0.001 to 2% by weight based on the weight of the plastic base.

16. The ophthalmic lens of claim 1 , wherein a light cut of the ophthalmic lens is higher than 402 nm.

17. The ophthalmic lens of claim 1 , wherein a Yellow Index of light transmitted through said ophthalmic lens is lower than 10.

18. The ophthalmic lens of claim 1 , wherein an average transmittance of the ophthalmic lens over the range 420-450 nm is less than 85%, wherein the average transmittance is measured on a bare lens.

19. A process for preparing the ophthalmic lens of claim 1 , comprising the steps of:
a) providing monomers or oligomers from which the plastic base can be prepared;
b) mixing the monomers or oligomers, the oxazolone and a catalyst suitable for the polymerization of the monomers and oligomers to form a polymerizable liquid composition;
c) curing the polymerizable liquid composition.

20. A method of absorbing blue light comprising:
a) obtaining an ophthalmic lens comprising an oxazolone as defined in claim 1 ;
b) positioning the lens in a position where it absorbs blue light.

Assignees

• Essilor Int

Inventors

• Iamsaard Supitchaya
• Fromentin Pierre

Classifications

• G02C7/10

  Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses · CPC title

• G02B3/0012

  characterised by the manufacturing method · CPC title

• C08K2201/011

  Nanostructured additives · CPC title

• C08K9/10

  Encapsulated ingredients · CPC title

• C08K5/353 Primary

  Five-membered rings · CPC title