Compositions with high refractive index and abbe number

Patent metadata

Field	Value
Publication number	US-11958923-B2
Application number	US-202318190018-A
Country	US
Kind code	B2
Filing date	Mar 24, 2023
Priority date	May 3, 2019
Publication date	Apr 16, 2024
Grant date	Apr 16, 2024

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. A composition made by free radical polymerization of a reactive monomer mixture comprising:
(a) at least one hydrophobic monomer;
(b) at least one hydrophilic monomer that is a poly(ethylene glycol) methyl ether methacrylate; and
(c) a tricyclo[5.2.1.0 2,6 ]decanedimethanol di(meth)acrylate cross-linking agent;

wherein the composition exhibits a refractive index of at least 1.45 and an Abbe number of at least 39.

2. The composition of claim 1 , wherein the hydrophobic monomer is a hydrophobic (meth)acrylate monomer selected from an aliphatic (meth)acrylate, an aromatic (meth)acrylate, a cycloaliphatic (meth)acrylate, and any combination thereof.

3. The composition of claim 2 , wherein the hydrophobic (meth)acrylate is a cycloaliphatic (meth)acrylate selected from cyclohexyl acrylate, cyclohexylmethyl acrylate, cyclohexylmethyl methacrylate, 2-cyclohexylethyl acrylate, 2-cyclohexylethyl methacrylate, ethylene glycol dicyclopentenyl ether acrylate, and any combination thereof.

4. The composition of claim 2 , wherein the hydrophobic (meth)acrylate is an aliphatic (meth)acrylate selected from C 1 -C 18 alkyl (meth)acrylates.

5. The composition of claim 2 , wherein the hydrophobic (meth)acrylate is an aromatic (meth)acrylate selected from the group consisting of 2-phenylethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 4-chlorophenoxyethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 3-phenoxypropyl (meth)acrylate, 1,3-bis-phenylthiol-2-propyl (meth)acrylate, poly(ethylene glycol) phenyl ether (meth)acrylate, and any combination thereof.

6. The composition 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, 1,1-dimethyl-2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and any combination thereof.

7. The composition of claim 1 , wherein the reactive monomer mixture comprises a mixture of the hydrophilic monomer and a hydroxyalkyl (meth)acrylate monomer, wherein the hydroxyalkyl (meth)acrylate monomer is 2-hydroxyethyl acrylate.

8. The composition of claim 1 , wherein the tricyclo[5.2.1.0 2,6 ]decanedimethanol di(meth)acrylate cross-linking agent is tricyclo[5.2.1.0 2,6 ]decanedimethanol diacrylate.

9. The composition 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-methacrylyloxyethylphenyl)-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 composition of claim 1 , further comprising at least one diluent in the reactive monomer mixture.

11. The composition of claim 1 , having a water content of between about 0 weight percent and about 15 weight percent.

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

13. The composition of claim 1 , wherein the free radical polymerization is a photopolymerization using a bisacylphosphine oxide initiator.

14. An ophthalmic device comprising the composition of claim 1 .

15. The ophthalmic device of claim 14 wherein the ophthalmic device comprises an intraocular lens, contact lens, corneal inlay, corneal outlay, or corneal insert.

16. A method for making an ophthalmic device, 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.

17. The composition of claim 3 , wherein the cycloaliphatic (meth)acrylate is ethylene glycol dicyclopentenyl ether acrylate.

18. The composition of claim 6 , wherein the hydroxyalkyl (meth)acrylate monomer is 4-hydroxybutyl acrylate.

19. The composition of claim 4 , wherein the aliphatic (meth)acrylate comprises a C 4 -C 8 linear alkyl group.

20. The composition of claim 2 , wherein the reactive monomer mixture comprises the at least one cycloaliphatic (meth)acrylate in an amount between 50 and 80 weight percent.

21. The composition of claim 1 , wherein the reactive monomer mixture comprises the tricyclo[5.2.1.0 2,6 ]decanedimethanol di(meth)acrylate cross-linking agent in an amount between 1 and 20 weight percent.

22. The composition of claim 11 , having a water content of between about 1 weight percent and about 10 weight percent.

23. The composition of claim 11 , having a water content of between about 1 weight percent and about 8 weight percent.

24. The composition of claim 12 , wherein the composition has a refractive index of at least 1.48 and an Abbe number of at least 50.

25. The composition of claim 12 , wherein the composition has a refractive index of at least 1.50 and an Abbe number of at least 50.

Assignees

• Johnson & Johnson Surgical Vision Inc

Inventors

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

Classifications

• 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

• C08F220/54

  Amides {, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide} · CPC title

• C08F220/30

  containing aromatic rings in the alcohol moiety · CPC title