High water content ophthalmic devices

Patent metadata

Field	Value
Publication number	US-10816698-B2
Application number	US-201816100693-A
Country	US
Kind code	B2
Filing date	Aug 10, 2018
Priority date	Aug 10, 2018
Publication date	Oct 27, 2020
Grant date	Oct 27, 2020

Abstract

An ophthalmic device is disclosed which is a polymerization product of a monomeric mixture comprising: (a) a major amount of one or more first non-silicone-containing hydrophilic monomers; (b) one or more hydrophobic monomers; and (c) a crosslinking agent mixture comprising (i) one or more di-, tri- or tetra(meth)acrylate-containing crosslinking agents and (ii) one or more di-, tri- or tetracarbamate-containing crosslinking agents, wherein the ophthalmic device has an equilibrium water content of at least about 65 weight percent.

First claim

What is claimed is:

1. An ophthalmic device which is a polymerization product of a monomeric mixture comprising:
(a) a major amount of cyclic lactam;
(b) a minor amount of one or more second non-silicone-containing hydrophilic monomers, wherein at least one of the one or more second non-silicone-containing hydrophilic monomers is a non-silicone-containing amide hydrophilic monomer;
(c) one or more hydrophobic monomers; and
(d) a crosslinking agent mixture comprising (i) one or more di-, tri- or tetra(meth)acrylate-containing crosslinking agents and (ii) one or more di-, tri- or tetracarbamate-containing crosslinking agents;
wherein the ophthalmic device has an equilibrium water content of at least about 65 weight percent.

2. The ophthalmic device of claim 1 , wherein the major amount of the cyclic lactam present in the monomeric mixture is an amount greater than about 80 weight percent, based on the total weight of the monomeric mixture.

3. The ophthalmic device of claim 1 , wherein the cyclic lactam is selected from the group consisting of N-vinyl-2-pyrrolidone, N-vinyl caprolactam, N-vinyl-2-piperidone and mixtures thereof.

4. The ophthalmic device of claim 1 , wherein the non-silicone-containing amide hydrophilic monomer is selected from the group consisting of an N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, N-(2-hydroxyethyl)methacrylamide and mixtures thereof.

5. The ophthalmic device of claim 1 , wherein the minor amount of the one or more second non-silicone-containing hydrophilic monomers present in the monomeric mixture is an amount of about 0.25 to about 10 weight percent, based on the total weight of the monomeric mixture.

6. The ophthalmic device of claim 1 , wherein the one or more second non-silicone-containing hydrophilic monomers further include 2-hydroxyethyl methacrylate, glyceryl methacrylate, N-methacryloyl glycine, (2-hydroxy-3-methacryloylpropyl)-4-methoxy phenylether or mixtures thereof.

7. The ophthalmic device of claim 1 , wherein the one or more hydrophobic monomers are represented by the structure of Formula I:

wherein R 1 is methyl or hydrogen; R 2 is —O— or —NH—; R 3 and R 4 are independently a divalent radical selected from the group consisting of —CH 2 —, —CHOH— and —CHR 6 —; R 5 and R 6 are independently a branched C 3 -C 8 alkyl group; R 7 is hydrogen or —OH; n is an integer of at least 1, and m and p are independently 0 or an integer of at least 1, provided that the sum of m, p and n is 2, 3, 4 or 5.

8. The ophthalmic device of claim 1 , wherein the one or more hydrophobic monomers are present in the monomeric mixture in an amount of about 0.5 to about 25 weight percent, based on the total weight of the monomeric mixture.

9. The ophthalmic device of claim 1 , wherein the one or more di-, tri- or tetra(meth)acrylate-containing crosslinking agents are one or more alkanepolyol di-, tri- or tetra(meth)acrylate-containing crosslinking agents.

10. The ophthalmic device of claim 1 , wherein the one or more di-, tri- or tetra(meth)acrylate-containing crosslinking agents are selected from the group consisting of an ethylene glycol di(meth)acrylate crosslinking agent having up to about 10 ethylene glycol repeating units, butanediol di(meth)acrylate crosslinking agent, trimethylol propane trimethacrylate crosslinking agent, pentaerythritol tetramethacrylate crosslinking agent and mixtures thereof.

11. The ophthalmic device of claim 1 , wherein the one or more di-, tri- or tetracarbamate-containing crosslinking agents are selected from the group consisting of a di(N-vinylcarbamate)-containing crosslinking agent, a di(N-allylcarbamate)-containing crosslinking agent, a di(O-vinylcarbamate)-containing crosslinking agent, a di(O-allylcarbamate)-containing crosslinking agent, a tri(N-vinylcarbamate)-containing crosslinking agent, a tri(N-allylcarbamate)-containing crosslinking agent, a tri(O-vinylcarbamate)-containing crosslinking agent, a tri(O-allylcarbamate)-containing crosslinking agent, a tetra(N-vinylcarbamate)-containing crosslinking agent, a tetra (N-allylcarbamate)-containing crosslinking agent, a tetra(O-vinylcarbamate)-containing crosslinking agent, a tetra(O-allylcarbamate)-containing crosslinking agent, and mixtures thereof.

12. The ophthalmic device of claim 1 , wherein the one or more di-carbamate-containing crosslinking agents are selected from the group consisting of diethylene glycol bis(N-vinylcarbamate), diethylene glycol bis(N-allylcarbamate), diethyl ene glycol bis(O-vinylcarbamate), diethylene glycol bis(O-allylcarbamate), and mixtures thereof.

13. The ophthalmic device of claim 1 , wherein the one or more di-, tri- or tetra(meth)acrylate-containing crosslinking agents are present in the monomeric mixture in an amount of about 0.1 to about 10.0 weight percent, based on the total weight of the monomeric mixture, and the one or more di-, tri- or tetracarbamate-containing crosslinking agents are present in the monomeric mixture in an amount of about 0.1 to about 5.0 weight percent, based on the total weight of the monomeric mixture.

14. The ophthalmic device of claim 1 , wherein the monomeric mixture further comprises one or more polymerizable surfactants selected from the group consisting of a poloxamer di(meth)acrylate, a reverse poloxamer di(meth)acrylate, a poloxamine di(meth)acrylate, a reverse poloxamine di(meth)acrylate and mixtures thereof.

15. The ophthalmic device of claim 1 , wherein the monomeric mixture further comprises an ultraviolet (UV) blocker.

16. The ophthalmic device of claim 15 , wherein the UV blocker is a compound of the formula

17. The ophthalmic device of claim 1 , wherein the ophthalmic device is a contact lens.

18. The ophthalmic device of claim 1 , wherein the ophthalmic device is a hydrogel.

19. The ophthalmic device of claim 1 , wherein the monomeric mixture contains no silicone-containing monomer.

20. A method of making an ophthalmic device comprising
(a) providing a monomeric mixture comprising:
(i) a major amount of one or more first non silicone containing hydrophilic monomers a cyclic lactam;
(ii) a minor amount of one or more second non-silicone-containing hydrophilic monomers, wherein at least one of the one or more second non-silicone-containing hydrophilic monomers is a non-silicone-containing amide hydrophilic monomer;
(iii) one or more hydrophobic monomers; and
(iv) a crosslinking agent mixture comprising (1) one or more di-, tri- or tetra(meth)acrylate-containing crosslinking agents and (2) one or more di-, tri- or tetracarbamate-containing crosslinking agents;

(b) subjecting the monomeric mixture to polymerizing conditions to provide a polymerized device, and
(c) extracting the polymerized device;
wherein the ophthalmic device has an equilibrium water content of at least about 65 weight percent.

21. The method of claim 20 , wherein the minor amount of the one or more second non-silicone-containing hydrophilic monomers present in the monomeric mixture is an amount of about 0.25 to about 10 weight percent, based on the total weight of the monomeric mixture.

22. The method of claim 20 , wherein the cyclic lactam is selected from the group consisting of N-vinyl-2-pyrrolidone, N-vinyl caprolactam, N-vinyl-2-piperidone and mixtures thereof, and the non-silicone-containing am

Assignees

• Bausch & Lomb

Inventors

• Nuñez Ivan M
• Poetz Katie L
• Hoff Joseph W
• Morgan Judith Chapman

Classifications

• C08F220/18

  with acrylic or methacrylic acids · CPC title

• G02B1/043 Primary

  Contact lenses · CPC title

• G02C7/04

  Contact lenses for the eyes (disinfection or sterilisation of contact lenses A61L12/00) · CPC title

• C08F26/10

  N-Vinyl-pyrrolidone · CPC title

• C07C269/00

  Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups [IMAGE cpc-sch-C07C-0964.gif], the nitrogen atom not being part of nitro or nitroso groups · CPC title