Compositions with high refractive index and abbe number

Patent metadata

Field	Value
Publication number	US-2026028439-A1
Application number	US-202519351233-A
Country	US
Kind code	A1
Filing date	Oct 6, 2025
Priority date	May 3, 2019
Publication date	Jan 29, 2026
Grant date	—

Abstract

Disclosed are co-polymers which are produced from reactive monomer mixtures and which have both high refractive index and a high Abbe number. These materials are well suited for use as implantable ophthalmic devices and have a refractive index which may be edited through application of energy. When used for an intraocular lens, the high refractive index allows for a thin lens which compresses to allow a small incision size.

First claim

We claim:

1 . An ophthalmic device comprising a composition made by free radical polymerization of a reactive monomer mixture, the reactive monomer mixture comprising:
a. at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring; b. at least one monomer selected from hydrophilic monomers and hydroxyalkyl (meth)acrylate monomers, and any combination thereof; and c. at least one cross-linking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39; and wherein the ophthalmic device comprises an intraocular lens, contact lens, corneal inlay, corneal outlay, or corneal insert.

2 . The ophthalmic device of claim 1 , wherein the at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring comprises two or more separate monocyclic cycloaliphatic rings, or a single bicyclic, tricyclic, bridged, fused, and/or spirocyclic cycloaliphatic ring system.

3 . The ophthalmic device of claim 1 , wherein the at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring is ethylene glycol dicyclopentenyl ether acrylate.

4 . The ophthalmic device of claim 1 , wherein the at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring is 2-(((3aR,4R,5S,7R,7aR)-octahydro-1H-4,7-methanoinden-5-yl)oxy) ethyl acrylate.

5 . The ophthalmic device of claim 1 , wherein the reactive monomer mixture comprises at least one hydrophilic monomer that is a poly(ethylene glycol)-containing monomer selected from poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate.

6 . The ophthalmic device of claim 1 , wherein the reactive monomer mixture comprises at least one hydroxyalkyl (meth)acrylate monomer selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, dimethylhydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof.

7 . The ophthalmic device of claim 6 , wherein the hydroxyalkyl (meth)acrylate monomer is 4-hydroxybutyl acrylate.

8 . The ophthalmic device of claim 1 , wherein the reactive monomer mixture comprises a mixture of a hydrophilic monomer and a hydroxyalkyl (meth)acrylate monomer, wherein the hydrophilic monomer is selected from poly(ethylene glycol) methacrylate and poly(ethylene glycol) methyl ether methacrylate, and wherein the hydroxyalkyl (meth)acrylate monomer is 2-hydroxyethyl acrylate.

9 . The ophthalmic device of claim 1 , wherein the reactive monomer mixture further comprises at least one cycloaliphatic (meth)acrylate containing one cycloaliphatic ring.

10 . The ophthalmic device of claim 9 , wherein the cycloaliphatic (meth)acrylate containing one cycloaliphatic ring is selected from cyclohexyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexylmethyl (meth)acrylate, 2-cyclohexylethyl (meth)acrylate, 3-cyclohexylpropyl (meth)acrylate, and any combination thereof.

11 . The ophthalmic device of claim 1 , wherein the reactive monomer mixture further comprises at least one aromatic (meth)acrylate selected from 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis(phenylthio)-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof.

12 . The ophthalmic device of claim 1 , wherein the reactive monomer mixture further comprises a hydroxyalkyl (meth)acrylate selected from 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, dimethylhydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof.

13 . The composition of claim 1 , wherein the cross-linking agent is a cycloaliphatic cross-linking agent comprising a cycloaliphatic group having between one and four cycloaliphatic rings.

14 . The composition of claim 13 , wherein the cycloaliphatic cross-linking agent is tricyclo[5.2.1.0 2,6 ]decanedimethanol di(meth)acrylate.

15 . The ophthalmic device of claim 1 , further comprising at least one UV/HEV absorbing compound in the reactive monomer mixture, wherein the UV/HEV absorbing compound is selected from 2-(2′-hydroxy-5-methacryloyloxyethylphenyl)-2H-benzotriazole, 2-(2-cyano-2-(9H-thioxanthen-9-ylidene) acetamido) ethyl methacrylate, 2-(2-cyano-2-(9H-xanthen-9-ylidene) acetamido) ethyl methacrylate, 2-(2-cyano-2-(10-methylacridin-9 (10H)-ylidene) acetamido) ethyl methacrylate, 3-(3-(tert-butyl)-5-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenyl)propyl methacrylate, and a compound of formula (II):

wherein:
m and n are independently 0, 1, 2, 3, or 4;
T is a bond, O, or NR;
X is O, S, NR, SO, or SO 2 ;
Y is a linking group;
P g is a polymerizable group;
R at each occurrence is independently H, C 1 -C 6 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or Y—P g ;
R 1 and R 2 , when present, are independently at each occurrence C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 thioalkyl, C 3 -C 7 cycloalkyl, aryl, halo, hydroxy, amino, NR 3 R 4 , or benzyl, wherein R 3 and R 4 are independently H or C 1 -C 6 alkyl, or two adjacent R 1 or R 2 groups, together with the carbon atoms to which they are attached, combine to form a cycloalkyl or aryl ring; and

EWG is an electron withdrawing group;
and any combination thereof.

16 . The ophthalmic device of claim 1 , further comprising at least one diluent in the reactive monomer mixture.

17 . The ophthalmic device claim 1 , having a water content of between about 0 weight percent and about 15 weight percent.

18 . The ophthalmic device of claim 1 , wherein the composition has a refractive index of at least 1.45 and an Abbe number of at least 45.

19 . The ophthalmic device of claim 1 , wherein the free radical polymerization is a photopolymerization using a bisacylphosphine oxide initiator.

20 . A method for making the ophthalmic device of claim 1 , the method comprising:
(a) providing a composition made by free radical polymerization of a reactive monomer mixture of claim 1 ; and (b) forming an ophthalmic device.

21 . The method of claim 20 , further comprising a step of extracting the ophthalmic device with a solvent.

22 . The method of claim 21 , further comprising a step of hydrating the extracted ophthalmic device with at least one aqueous solution.

23 . A method for making the ophthalmic device of claim 1 , the method comprising:
a. preparing a blank from a composition made by free radical polymerization of the composition of claim 1 ; b. machining an ophthalmic device from the blank.

24 . The method of claim 23 , further comprising the step of extracting the ophthalmic device with a solvent.

25 . The method of claim 24 , further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

26 . A method for making the ophthalmic device of claim 1 , the method comprising molding the device from a composition comprising:
a. at least one cycloaliphatic (meth)acrylate monomer containing more than one cycloaliphatic ring; b. at least

Assignees

• Johnson & Johnson Surgical Vision Inc

Inventors

• Alli Azaam
• Johnson Bart A
• Joslin Scott L
• Maharvi Ghulam

Classifications

• G02B1/041

  Lenses · CPC title

• C08F220/40 Primary

  Esters of unsaturated alcohols {, e.g. allyl (meth)acrylate} · CPC title

• C08L33/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C08L33/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08F220/20

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title