Water extractable ophthalmic devices

Patent metadata

Field	Value
Publication number	US-11897985-B2
Application number	US-202217729181-A
Country	US
Kind code	B2
Filing date	Apr 26, 2022
Priority date	May 15, 2018
Publication date	Feb 13, 2024
Grant date	Feb 13, 2024

Abstract

A water extractable ophthalmic device is disclosed which is a polymerization product of a monomeric mixture comprising: (a) one or more cyclic lactams; (b) one or more non-bulky organosilicon-containing monomers; (c) one or more bulky siloxane monomers; and (d) a crosslinking agent mixture comprising (i) one or more first crosslinking agents containing at least two ethylenically unsaturated reactive end groups, wherein the at least two ethylenically unsaturated reactive end groups are (meth)acrylate-containing reactive end groups and (ii) one or more second crosslinking agents containing at least two ethylenically unsaturated reactive end groups wherein at least one of the ethylenically unsaturated reactive end groups is a non-(meth)acrylate reactive end group. The water extractable ophthalmic device has an equilibrium water content of at least about 50 wt. %, a contact angle of less than about 50°, and an oxygen permeability of at least about 60 Barrers.

First claim

What is claimed is:

1. A method of preparing a water extractable ophthalmic device, the method comprising:
(a) curing a monomeric mixture in a mold, the monomeric mixture comprising (i) one or more cyclic lactams; (ii) one or more non-bulky organosilicon-containing monomers; (ii) one or more bulky siloxane monomers; and (iv) a crosslinking agent mixture comprising (1) one or more first crosslinking agents containing at least two ethylenically unsaturated reactive end groups, wherein the at least two ethylenically unsaturated reactive end groups are (meth)acrylate-containing reactive end groups and (2) one or more second crosslinking agents containing at least two ethylenically unsaturated reactive end groups wherein at least one of the ethylenically unsaturated reactive end groups is a non-(meth)acrylate reactive end group; and
(b) dry releasing the ophthalmic device from the mold to provide a water extractable ophthalmic device having an equilibrium water content of at least about 50 wt. %, a contact angle of less than about 50°, and an oxygen permeability of at least about 60 Barrers;
wherein the one or more second crosslinking agents are represented by the following structure:

wherein R is hydrogen or methyl; X is O; Y is O or NH; Z is NH; W is O and n is from 2 to 6.

2. The method of claim 1 , wherein the water extractable ophthalmic device further has a water extractable content of less than about 15 wt. %.

3. The method of claim 1 , wherein the one or more cyclic lactams are selected from the group consisting of N-vinyl-2-pyrrolidone, N-vinyl caprolactam, N-vinyl-2-piperidone and mixtures thereof.

4. The method of claim 1 , wherein the one or more non-bulky organosilicon- containing monomers comprise a compound represented by the following structure:

wherein L is ethylenically unsaturated polymerizable group, V is a linker group or a bond; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently hydrogen, alkyl, haloalkyl, cycloalkyl, heterocycloalkyl, alkenyl, haloalkenyl, and aromatic; R 10 and R 11 are independently hydrogen or an alkyl group wherein at least one of R 10 and R 11 is hydrogen; y is 2 to 7 and n is 1 to 100, or a compound represented by the following structure:

wherein R 12 is H or methyl; X is O or NR 16 ; wherein R 16 is hydrogen or C 1 to C 4 alkyl, which may be further substituted with one or more hydroxyl groups; R 13 is a divalent alkyl group, which may further be functionalized with a group selected from the group consisting of an ether group, a hydroxyl group, a carbamate group and combinations thereof; each R 14 is independently a phenyl or a C 1 to C 4 alkyl group which may be substituted with fluorine, hydroxyl or ether; R 15 is a C 1 to C 4 alkyl; and a is 2 to 50.

5. The method of claim 1 , wherein the one or more bulky siloxane monomers are selected from the group consisting of methacryloxypropyl tris(trimethylsiloxy)silane, pentamethyldisiloxanyl methylmethacrylate, tris(trimethylsiloxy)methacryloxy propylsilane, phenyltretramethyl-disloxanylethyl acrylate, methyldi(trimethylsiloxy)methacryloxymethyl silane, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate, 3-[tris(trimethylsiloxy)silyl]propyol allyl carbamate, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate and mixtures thereof.

6. The method of claim 1 , wherein the one or more first crosslinking agents are selected from the group consisting of an alkylene glycol-containing di(meth)acrylate crosslinking agent, an alkylene glycol-containing tri(meth)acrylate crosslinking agent, an alkylene glycol-containing tetra(meth)acrylate crosslinking agent and mixtures thereof.

7. The method of claim 1 , wherein the monomeric mixture comprises:
(i) about 42 wt. % to about 55 wt. %, based on the total weight of the monomeric mixture, of the one or more cyclic lactams;
(ii) about 5 to about 25 wt. %, based on the total weight of the monomeric mixture, of the one or more non-bulky organosilicon-containing monomers;
(iii) about 10 to about 45 wt. %, based on the total weight of the monomeric mixture, of the one or more bulky siloxane monomers; and
(iv) a crosslinking agent mixture comprising (i) about 0.05 to about 2 wt. %, based on the total weight of the monomeric mixture, of the one or more first crosslinking agents and (ii) about 0.05 to about 3 wt. %, based on the total weight of the monomeric mixture, of the one or more second crosslinking agents.

8. The method of claim 1 , wherein the monomeric mixture further comprises a minor amount of 2-hydroxyethyl methacrylate (HEMA).

9. The method of claim 1 , wherein the monomeric mixture further comprises an ultraviolet (UV) blocker.

10. The method of claim 1 , wherein the water extractable ophthalmic device is one of a contact lens and a hydrogel.

11. The method of claim 1 , wherein the step of curing comprises one of thermal curing or infrared curing.

12. The method of claim 1 , wherein the water extractable ophthalmic device has an equilibrium water content of from about 50 wt. % to about 70 wt. %, a contact angle of from about 30° to about 50° , and an oxygen permeability of at least about 70 Barrers.

13. A method of preparing a water extractable ophthalmic device, the method comprising:
(a) curing a monomeric mixture in a mold, the monomeric mixture comprising (i) one or more cyclic lactams; (ii) one or more non-bulky organosilicon-containing monomers; (ii) one or more bulky siloxane monomers; and (iv) a crosslinking agent mixture comprising (1) one or more first crosslinking agents containing at least two ethylenically unsaturated reactive end groups, wherein the at least two ethylenically unsaturated reactive end groups are (meth)acrylate-containing reactive end groups and (2) about 0.01 to about 3 wt. %, based on the total weight of the monomeric mixture, of one or more second crosslinking agents containing at least two ethylenically unsaturated reactive end groups, wherein at least one of the ethylenically unsaturated reactive end groups is a non-(meth)acrylate reactive end group; and wherein at least one of the one or more second crosslinking agents are represented by the following structure:

wherein x is from 2 to 10; and
(b) dry releasing the ophthalmic device from the mold to provide the water extractable ophthalmic device.

14. The method of claim 13 , wherein the one or more cyclic lactams are selected from the group consisting of N-vinyl-2-pyrrolidone, N-vinyl caprolactam, N-vinyl-2-piperidone and mixtures thereof.

15. The method of claim 13 , wherein the one or more non-bulky organosilicon-containing monomers comprise a compound represented by the following structure:

wherein L is ethylenically unsaturated polymerizable group, V is a linker group or a bond; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently hydrogen, alkyl, haloalkyl, cycloalkyl, heterocycloalkyl, alkenyl, haloalkenyl, and aromatic; R 10 and R 11 are independently hydrogen or an alkyl group wherein at least one of R 10 and R 11 is hydrogen; y is 2 to 7 and n is 1 to 100, or a compound represent

Assignees

• Bausch & Lomb

Inventors

• Nuñez Ivan M
• Coullard Lynn
• Mark Analuz
• Hoteling Andrew J
• Hoff Joseph W

Classifications

• C08F226/10 Primary

  N-Vinyl-pyrrolidone · CPC title

• B29D11/00134

  Curing of the contact lens material · CPC title

• C08J3/075

  Macromolecular gels · CPC title

• C08J3/24

  Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K) · CPC title

• G02B1/043 Primary

  Contact lenses · CPC title