Process for manufacturing light absorbing polymer matrix

Patent metadata

Field	Value
Publication number	US-11725136-B2
Application number	US-201816958440-A
Country	US
Kind code	B2
Filing date	Dec 19, 2018
Priority date	Dec 29, 2017
Publication date	Aug 15, 2023
Grant date	Aug 15, 2023

Abstract

An ophthalmic lens comprising a transparent polymer matrix and core shell nanoparticles which are dispersed in the transparent polymer matrix, wherein the core of core shell nanoparticles results from polymerization of a composition comprising nanoparticle core precursors and at least one photochromic compound, and the shell of core shell nanoparticles comprises a mineral compound.

First claim

The invention claimed is:

1. An ophthalmic lens comprising a transparent polymer matrix and core-shell nanoparticles which are dispersed in the transparent polymer matrix, wherein:
the core of the core-shell nanoparticles results from polymerization of a composition comprising nanoparticle core precursors and at least one photochromic compound; and
the shell of the core-shell nanoparticles comprises a mineral compound;
wherein the core of the core-shell nanoparticles comprises the at least one photochromic compound embedded within the core, wherein the amount of the at least one photochromic compound in the core-shell nanoparticles is from 0.0001 to 90 wt % based on the total weight of the core-shell nanoparticles;
wherein the nanoparticle core precursors comprise an alkylalkoxysilane monomer further defined as tetraethyloxysilane (TEOS), tetramethyloxysilane (TMOS), methyltriethoxysilane (MTES), dimethyldiethoxysilane (DMDES), or a mixture thereof and/or an organically modified alkoxysilane monomer further defined as epoxysilane, epoxydialkoxysilanes, epoxytrialkoxysilanes, aminosilanes, or a mixture thereof; and
wherein the amount of the core-shell nanoparticles in the transparent polymer matrix is from 0.001 to 2 wt % based on the weight of the transparent polymer matrix.

2. The ophthalmic lens according to claim 1 , wherein a molar absorption coefficient of the at least one photochromic compound in a colored form is higher than 5000 L mol −1 cm −1 .

3. The ophthalmic lens according to claim 2 , wherein the molar absorption coefficient of the at least one photochromic compound in a colored form is 20000 L mol −1 cm −1 .

4. The ophthalmic lens according to claim 1 , wherein the amount of the at least one photochromic compound in the core-shell nanoparticles is from 0.01 to 50% wt % based on the total weight of the core-shell nanoparticles.

5. The ophthalmic lens according to claim 1 , wherein the transparent polymer matrix is any one of the following thermoplastic resins: polyamide, polyimide, polysulfone, polycarbonate, polyester, polyethylene terephthalate, poly(meth)acrylate, poly(methyl(meth)acrylate) (PMMA), polycyclic olefin copolymer, thermoplastic elastomers, thermoplastic urethanes, polycellulose triacetate or copolymers thereof, or wherein the transparent polymer matrix is any one of the following thermosetting resins: a homopolymer or copolymer of diallyl esters, a homopolymer or copolymer of diallyl carbonates of linear or branched aliphatic or aromatic polyols, a homopolymer or copolymer of (meth)acrylates, 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 sulfide, a homopolymer or copolymer of disulfide, a homopolymer or copolymer of episulfide, a homopolymer or copolymer of polythiol and polyisocyanate, and combinations thereof.

6. The ophthalmic lens according to claim 1 , wherein the shell of the core-shell nanoparticles comprises a mineral oxide further defined as SiO 2 , TiO 2 , ZrO 2 , Al 2 O 3 , ZnO, MgO or mixtures thereof.

7. The ophthalmic lens according to claim 1 , wherein the refractive index of the core-shell nanoparticles ranges from 1.47 to 1.74.

8. The ophthalmic lens according to claim 7 , wherein the refractive index of the core-shell nanoparticles is identical to the refractive index of the transparent polymer matrix.

9. The ophthalmic lens according to claim 1 , wherein the surface of the shell of the core-shell nanoparticles is functionalized with (meth)acrylic, vinylic, allylic, amine, glycidol, or thiol/mercapto groups.

10. The ophthalmic lens according to claim 9 , wherein the surface of the shell of the core-shell nanoparticles is functionalized by 3-acryloxypropyltrimethoxysilane, 3-acryloxypropyltriethoxysilane, 3-acryloxypropylmethyldimethoxysilane, 3-acryloxypropylmethyldiethoxysilane 3-acryloxypropyldimethylmethoxysilane, 3-acryloxypropyldimethylethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, allylmethyldimethoxysilane, allyldimethylethoxysilane, allyldimethylmethoxysilane, allyldimethylethoxysilane, 3-allyloxypropyltrimethoxysilane, 3-allyloxypropyltriethoxysilane, γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, 3-(glycidyloxypropyl)trimethoxysilane, 3-(glycidyloxypropyl)triethoxysilane, 3-mercaptopropyltrimethoxysilane or 3-mercaptopropyltriethoxysilane.

11. The ophthalmic lens according to claim 1 , wherein the size of the core-shell nanoparticles is from 1 nm to 10 μm, as measured according to the Dynamic Light Scattering method.

12. The ophthalmic lens according to claim 11 , wherein the size of the core-shell nanoparticles is from 10 nm to 5 μm, as measured according to the Dynamic Light Scattering method.

13. The ophthalmic lens according to claim 1 , wherein the amount of the core-shell nanoparticles in the transparent polymer matrix is from 0.0025 to 1 wt % based on the weight of the transparent polymer matrix.

14. The ophthalmic lens according to claim 1 , wherein the transparent polymer matrix is an optical substrate or a coating deposited on an optical substrate.

15. A process of preparation of an ophthalmic lens, comprising the steps of:
a) providing nanoparticle core precursors comprising an alkylalkoxysilane monomer further defined as tetraethyloxysilane (TEOS), tetramethyloxysilane (TMOS), methyltriethoxysilane (MTES), dimethyldiethoxysilane (DMDES), or a mixture thereof and/or an organically modified alkoxysilane monomer further defined as epoxysilane, epoxydialkoxysilanes, epoxytrialkoxysilanes, aminosilanes, or a mixture thereof mixed with a photochromic compound, wherein an amount of the at least one photochromic compound in the core-shell nanoparticles is from 0.0001 to 90 wt % based on the total weight of the core-shell nanoparticles;
b) polymerizing the nanoparticles core precursors so as to obtain nanoparticle cores encapsulating said photochromic compound;
c) forming a mineral shell on the nanoparticle cores encapsulating said photochromic compound so as to obtain core-shell nanoparticles encapsulating said photochromic compound;
d) providing a polymerizable transparent polymer matrix precursor;
e) mixing the transparent polymer matrix precursor and the core-shell nanoparticles;
f) curing the mixture obtained at step e) so as to obtain transparent polymer matrix in which are dispersed core-shell nanoparticles encapsulating said photochromic compound, wherein an amount of the core-shell nanoparticles in the transparent polymer matrix is from 0.001 to 2 wt % based on the weight of the transparent polymer matrix.

16. The process according to claim 15 , further comprising a step e1 between step e and step f, wherein step e1 consists in:
e1) depositing the mixture obtained at step e) on a substrate.

17. The process according to claim 15 , wherein the core-shell nanoparticles of step c are provided either in the form of a powder which is dispersible within the transparent polymer matrix precursor, or in the form of a dispersion of core-shell nanoparticles in a liquid which is dispersible within the transparent polymer precursor.

Assignees

• Essilor Int

Inventors

• Biteau John
• Berzon Ronald
• Fromentin Pierre

Classifications

• C09K9/02 Primary

  Organic tenebrescent materials · CPC title

• B01J13/18

  In situ polymerisation with all reactants being present in the same phase · CPC title

• B01J13/22

  Coating · CPC title

• C08L31/06

  Homopolymers or copolymers of esters of polycarboxylic acids · CPC title

• G02B1/041

  Lenses · CPC title