Compositions with high refractive index and Abbe number

Patent metadata

Field	Value
Publication number	US-12460032-B2
Application number	US-202418603133-A
Country	US
Kind code	B2
Filing date	Mar 12, 2024
Priority date	May 3, 2019
Publication date	Nov 4, 2025
Grant date	Nov 4, 2025

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; (b) at least one aliphatic (meth)acrylate comprising a linear or branched unsubstituted alkyl group; and (c) tricyclo[5.2.1.0 2,6 ]decanedimethanol di(meth)acrylate as a cycloaliphatic 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 cycloaliphatic (meth)acrylate comprises a cycloaliphatic group having between one and four cycloaliphatic rings.

3 . The ophthalmic device of claim 1 , wherein the cycloaliphatic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexylmethyl acrylate, 2-cyclohexylethylacrylate, 3-cyclohexylpropylacrylate, ethylene glycol dicyclopentenyl ether acrylate, and any combination thereof.

4 . The ophthalmic device of claim 1 , wherein the aliphatic (meth)acrylate comprises a linear or branched unsubstituted alkyl group containing between 1 and 25 carbon atoms.

5 . The ophthalmic device of claim 1 , further comprising a non-cycloaliphatic cross-linking agent selected from ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol tri(meth)acrylate, triallyl cyanurate, methylene bis(meth)acrylamide, poly(ethylene glycol) di(meth)acrylate, bis(2-hydropropyl (meth)acrylate) terminated polydimethylsiloxanes, and any combination thereof.

6 . The ophthalmic device of claim 1 , further comprising an aromatic (meth)acrylate or a hydroxyalkyl (meth)acrylate.

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

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

9 . 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, 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.

10 . 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.

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

12 . 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.

13 . The method of claim 12 , further comprising the step of extracting the ophthalmic device with a solvent.

14 . The method of claim 13 , further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

15 . 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.

16 . 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; b) at least one aliphatic (meth)acrylate comprising a linear or branched unsubstituted alkyl group; and c) tricyclo[5.2.1.0 2,6 ]decanedimethanol di(meth)acrylate as a cycloaliphatic cross-linking agent; wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39.

17 . The method of claim 16 , further comprising the step of extracting the ophthalmic device with a solvent.

18 . The method of claim 17 , further comprising the step of hydrating the extracted ophthalmic device with at least one aqueous solution.

19 . The ophthalmic device of claim 1 , wherein:
(a) the cycloaliphatic (meth)acrylate is selected from cyclohexyl acrylate, cyclohexylmethyl acrylate, 2-cyclohexylethylacrylate, 3-cyclohexylpropylacrylate, and ethylene glycol dicyclopentenyl ether acrylate; and (b) the aliphatic (meth)acrylate comprises a linear or branched unsubstituted alkyl group containing between 4 and 8 carbon atoms.

20 . The ophthalmic device of claim 19 , wherein the cycloaliphatic (meth)acrylate is cyclohexyl acrylate.

Assignees

• Johnson & Johnson Surgical Vision Inc

Inventors

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

Classifications

• G02B1/041

  Lenses · CPC title

• A61L2430/16

  for reconstruction of eye parts, e.g. intraocular lens, cornea · CPC title

• A61F2/16

  Intraocular lenses · CPC title

• A61L27/26

  Mixtures of macromolecular compounds · CPC title

• C08F222/102

  of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate · CPC title