Optical material with improved colour

Patent metadata

Field	Value
Publication number	US-11480713-B2
Application number	US-201816498041-A
Country	US
Kind code	B2
Filing date	Mar 27, 2018
Priority date	Mar 27, 2017
Publication date	Oct 25, 2022
Grant date	Oct 25, 2022

Abstract

Disclosed are polymerizable compositions for ophthalmic lenses. The compositions employ peroxide-based polymerization initiators with decreased capacity for dye degradation. The compositions enable the inclusion of color-balancing dyes, resulting in lenses with improved clarity and color balance.

First claim

The invention claimed is:

1. A polymerizable composition comprising:
a) at least one allyl monomer or oligomer;
b) at least one catalyst suitable for initiating the polymerization of said allyl monomer or oligomer;
c) at least one UV absorber; and
d) at least one dye;

wherein the at least one catalyst has the following formula:
R 1 —O—O—C(═O)—O—R 2 or R 1 —O—O—C(═O)—R 2

wherein R 1 is an alkyl chain having from 1 to 12 carbon atoms and R 2 is a multivalent polyether bound to a plurality of alkylperoxy carbonate groups; or wherein R 2 is an alkyl chain having from 1 to 12 carbon atoms and R 1 is a multivalent polyether bound to a plurality of alkylperoxy carbonate groups.

2. The polymerizable composition of claim 1 , wherein the allyl monomer or oligomer is ethylene glycol bis(allyl carbonate) or diethylene glycol bis(allyl carbonate), or an oligomer thereof, or a mixture thereof.

3. The polymerizable composition of claim 1 , wherein the at least one allyl monomer or oligomer is present in an amount ranging from 20 to 99.5% by weight, based on a total weight of the composition.

4. The polymerizable composition of claim 1 , wherein the catalyst R 1 and R 2 groups are saturated.

5. The polymerizable composition of claim 1 , wherein the catalyst alkyl chain comprises 3 to 8 carbon atoms.

6. The polymerizable composition of claim 1 , wherein the UV absorber is a benzophenone having the following structure:

wherein R 3 and R 4 are each independently H or an alkyl chain having from 1 to 12 carbon atoms.

7. The polymerizable composition of claim 6 , wherein R 3 and R 4 are methyl.

8. The polymerizable composition of claim 6 , wherein R 3 and R 4 are H.

9. The polymerizable composition of claim 1 , wherein R 1 or R 2 is bound to 2, 3 or 4 alkylperoxy carbonate groups.

10. A process for the manufacture of an ophthalmic lens, comprising polymerizing the polymerizable composition of claim 1 to form an ophthalmic lens.

11. An ophthalmic lens obtained by polymerizing a polymerizable composition comprising:
a) at least one allyl monomer or oligomer;
b) at least one catalyst suitable for initiating the polymerization of said allyl monomer or oligomer;
c) at least one UV absorber; and
d) at least one dye;

wherein the at least one catalyst has the following formula:
R 1 —O—O—C(═O)—O—R 2 of R 1 —O—O—C(═)—R 2

wherein R 1 is an alkyl chain having from 1 to 12 carbon atoms and R 2 is a multivalent polyether bound to a plurality of alkylperoxy carbonate groups; or wherein R 2 is an alkyl chain having from 1 to 12 carbon atoms and R 1 is a multivalent polyether bound to a plurality of alkylperoxy carbonate groups.

12. The ophthalmic lens of claim 11 , wherein the lens has a yellow index of less than 5.

13. The ophthalmic lens of claim 11 , wherein the lens has a haze value of less than 0.5%.

14. The ophthalmic lens of claim 11 , wherein the lens has a light-cut value of less than 410 nm.

15. The ophthalmic lens of claim 11 , wherein R 1 or R 2 is bound to 2, 3 or 4 alkylperoxy carbonate groups.

16. The polymerizable composition of claim 1 , wherein said polyether has from 5 to 30 carbon atoms.

17. The polymerizable composition of claim 1 , wherein the at least one allyl monomer or oligomer is present in an amount ranging from 50 to 99.5% by weight, based on a total weight of the composition.

18. The polymerizable composition of claim 1 , wherein the at least one allyl monomer or oligomer is present in an amount ranging from 80 to 99.5% by weight, based on a total weight of the composition.

Assignees

• Essilor Int

Inventors

• Lertwattanaseri Tipparat
• Fromentin Pierre

Classifications

• G02B1/041 Primary

  Lenses · CPC title

• G02C7/022

  Ophthalmic lenses having special refractive features achieved by special materials or material structures (G02C7/049 takes precedence) · CPC title

• G02C7/108

  Colouring materials · CPC title

• C08F18/24

  Esters of carbonic or haloformic acids · CPC title