Composition for the manufacture of an ophthalmic lens comprising an encapsulated light-absorbing additive

Patent metadata

Field	Value
Publication number	US-11635547-B2
Application number	US-201816770466-A
Country	US
Kind code	B2
Filing date	Nov 15, 2018
Priority date	Dec 8, 2017
Publication date	Apr 25, 2023
Grant date	Apr 25, 2023

Abstract

The present invention relates to an ophthalmic lens which efficiently absorbs light rays without degradation of the light-absorbing additive, said ophthalmic lens comprising a composite matrix, a catalyst, a UV absorber and at least one light-absorbing additive contained in nanoparticles which are dispersed in said allyl monomer or allyl oligomer.

First claim

The invention claimed is:

1. An ophthalmic lens comprising a composite substrate comprising:
a) a matrix obtained by polymerization of at least one allyl or non-allyl monomer or oligomer in presence of a catalyst for initiating the polymerization of said monomer or oligomer;
b) at least one light-absorbing additive contained in nanoparticles which are dispersed in said matrix; and
c) at least one UV absorber,

wherein the optical transmittance through a 2 mm thick ophthalmic lens is lower than 1% for each light wavelength ranging from 280 to 400 nm, and higher than 65% for light having a wavelength of 430 nm.

2. The ophthalmic lens according to claim 1 , wherein the matrix is a thermoplastic resin or is a thermosetting resin.

3. The ophthalmic lens according to claim 1 , wherein the light-absorbing additive is a colorant, a colorless light-absorbing additive or mixtures thereof.

4. The ophthalmic lens according to claim 1 , wherein the nanoparticles comprise a polymer selected from the group consisting of an acrylic polymer, a vinylic polymer, an allylic polymer, and mixtures thereof.

5. The ophthalmic lens according to claim 1 , wherein nanoparticles comprise a mineral oxide.

6. The ophthalmic lens according to claim 1 , wherein the nanoparticles have a size of from 1 nm to 10 μm, as measured according to the Dynamic Light Scattering method.

7. The ophthalmic lens according to claim 1 , wherein the amount of light-absorbing additive in the nanoparticles is from 0.01 to 50% wt %, based on the weight of the nanoparticles.

8. The ophthalmic lens according to claim 1 , wherein the amount of nanoparticles in the composition is from 0.001 wt % to lwt %, based on the weight of the composition.

9. The ophthalmic lens according to claim 1 , wherein the at least one UV absorber is a:
a) Benzophenone derivative; or
b) Benzotriazole derivative; or
c) Chlorobenzotriazole compound having at least one ester group,

with the proviso that the chlorobenzotriazole compound does not comprise any polymerizable group selected from allylic, acrylic and methacrylic moieties; or
d) 2-(2-hydroxy-5-R 1 -phenyl)benzotriazole, in which R 1 is a resonant group selected from the groups amino, hydroxyl, alkoxy, aryloxy, alkylamino, arylamino, dialkylamino, diarylamino, (aryl)(alkyl)amino, formamido, alkylamido, arylamido, formyloxy, alkylcarboxy, arylcarboxy, alkylimino, and arylimino; or
e) Triazine derivative; or
f) Oxalanilide derivative; or
g) Mixtures thereof.

10. A process for preparing the ophthalmic lens according to claim 1 , comprising the steps of:
a) providing monomers or oligomers from which the matrix can be prepared;
b) preparing a light-absorbing additive contained in nanoparticles in the form of a powder which is dispersible within the monomers or oligomers or in the form of a dispersion of nanoparticles in a liquid which is dispersible within the monomers or oligomers;
c) providing a catalyst for initiating the polymerization of said monomers or oligomers;
d) providing a UV absorber;
e) mixing the monomers or oligomers, the nanoparticles the catalyst and UV absorber so as to obtain a polymerizable liquid composition in which nanoparticles are dispersed;
f) optionally depositing the polymerizable liquid composition on a substrate; and
g) curing the polymerizable liquid composition.

11. The ophthalmic lens according to claim 2 , wherein the thermoplastic resin is a polyamide, polyimide, polysulfone, polycarbonate, polyethylene terephthalate, poly(methyl(meth)acrylate), cellulose triacetate or copolymers thereof.

12. The ophthalmic lens according to claim 2 , wherein the thermosetting resin is a cyclic olefin copolymer, a homopolymer or copolymer of allyl esters, a homopolymer or copolymer of allyl carbonates of linear or branched aliphatic or aromatic polyols, a homopolymer or copolymer of (meth)acrylic acid and esters thereof, a homopolymer or copolymer of thio(meth)acrylic acid and esters thereof, a homopolymer or copolymer of urethane and thiourethane, a homopolymer or copolymer of epoxy, a homopolymer or copolymer of sulphide, a homopolymer or copolymer of disulphide, a homopolymer or copolymer of episulfide, a homopolymer or copolymer of thiol and isocyanate, or a combination thereof.

13. The ophthalmic lens according to claim 3 , wherein the colorant is a dye or a pigment.

14. The ophthalmic lens according to claim 5 , wherein the nanoparticles comprise a mineral oxide comprising SiO 2 , TiO 2 , ZrO 2 , Al 2 O 3 , or a mixture thereof.

15. The ophthalmic lens according to claim 6 , wherein the nanoparticles have a size of from 10 nm to 5 μm, as measured according to the Dynamic Light Scattering method.

16. The ophthalmic lens according to claim 7 , wherein the amount of light-absorbing additive in the nanoparticles is from 0.1 to 10 wt % based on the weight of the nanoparticles.

17. The ophthalmic lens according to claim 9 , wherein the benzophenone derivatives are 2,2′-dihydroxy-4,4′-dimethoxybenzophenone, 2,2′-dihydroxy-4-methoxybenzophenone and 2,2′,4,4′-tetrahydroxybenzophenone.

18. The ophthalmic lens according to claim 9 , wherein the benzotriazole derivatives are 2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-5-chloro-2H-benzotriazole and 2-(2H-benzotriazole-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1,3,3- tetramethylbutyl)phenol.

19. The ophthalmic lens according to claim 9 , wherein the chlorobenzotriazole compound is a compound of formula (IV):

in which A is a divalent group, R 1 is a chloro group, the R 2 groups are identical or different monovalent groups, n is a integer ranging from 1 to 3, and R 3 is a linear or branched, substituted or unsubstituted alkyl or aryl group.

20. The ophthalmic lens according to claim 9 , wherein the 2-(2-hydroxy-5-R 1 -phenyl)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.

Assignees

• Essilor Int

Inventors

• Fromentin Pierre
• Lertwattanaseri Tipparat

Classifications

• C08K3/22

  of metals · CPC title

• B82Y40/00

  Manufacture or treatment of nanostructures · CPC title

• G02B1/041 Primary

  Lenses · CPC title

• C08F222/1025

  of aromatic dialcohols · CPC title

• C08L2205/22

  Mixtures comprising a continuous polymer matrix in which are dispersed crosslinked particles of another polymer · CPC title