Ophthalmic devices containing localized grafted networks and processes for their preparation and use

Patent metadata

Field	Value
Publication number	US-11034789-B2
Application number	US-201916239603-A
Country	US
Kind code	B2
Filing date	Jan 4, 2019
Priority date	Jan 30, 2018
Publication date	Jun 15, 2021
Grant date	Jun 15, 2021

Abstract

Provided are polymer compositions made by a process comprising: (a) providing a first reactive composition containing: (i) a polymerization initiator that is capable, upon a first activation, of forming two or more free radical groups, at least one of which is further activatable by subsequent activation; (ii) one or more ethylenically unsaturated compounds; and (iii) a crosslinker; (b) subjecting the first reactive composition to a first activation step such that the first reactive composition polymerizes therein to form a crosslinked substrate network containing a covalently bound activatable free radical initiator; (c) contacting the crosslinked substrate network with a grafting composition containing one or more ethylenically unsaturated compounds, wherein the contacting is conducted under conditions such that the grafting composition penetrates into the crosslinked substrate network; and (d) activating the covalently bound activatable free radical initiator at one or more selective regions of the crosslinked substrate network such that the grafting composition polymerizes with the crosslinked substrate network at the selective regions.

First claim

We claim:

1. An ophthalmic device formed by a process comprising:
(a) providing a first reactive composition containing: (i) a bisacylphosphine oxide polymerization initiator; (ii) one or more ethylenically unsaturated compounds; and (iii) a crosslinker;
(b) subjecting the first reactive composition to a first activation step such that the first reactive composition polymerizes therein to form a crosslinked substrate network containing a covalently bound activatable monoacylphosphine oxide free radical initiator;
(c) contacting the crosslinked substrate network with a grafting composition containing one or more ethylenically unsaturated compounds, wherein the contacting is conducted under conditions such that the grafting composition penetrates into the crosslinked substrate network; and
(d) activating the covalently bound monoacylphosphine oxide free radical initiator at one or more selective regions of the crosslinked substrate network such that the grafting composition polymerizes with the crosslinked substrate network at the selective regions.

2. The ophthalmic device of claim 1 wherein the grafting composition of step (c) contains a crosslinker.

3. The ophthalmic device of claim 1 wherein the grafting composition of step (c) is free of a crosslinker.

4. The ophthalmic device of claim 1 wherein the one or more ethylenically unsaturated compounds of step (a) comprise one or more polymerizable groups independently selected from: (meth)acrylate, (meth)acrylamide, styryl, vinyl, N-vinyl lactam, N-vinylamide, O-vinylether, O-vinylcarbonate, O-vinylcarbamate, C 2-12 alkenyl, C 2-12 alkenylphenyl, C 2-12 alkenylnaphthyl, and C 2-6 alkenylphenyl-C 1-6 alkyl.

5. The ophthalmic device of claim 1 wherein the one or more ethylenically unsaturated compounds of step (c) comprise one or more polymerizable groups independently selected from: (meth)acrylate, (meth)acrylamide, styryl, vinyl, N-vinyl lactam, N-vinylamide, O-vinylether, O-vinylcarbonate, O-vinylcarbamate, C 2-12 alkenyl, C 2-12 alkenylphenyl, C 2-12 alkenylnaphthyl, and C 2-6 alkenylphenyl-C 1-6 alkyl.

6. The ophthalmic device of claim 1 that is in the form of a hydrogel and wherein the first reactive composition contains one or more silicone-containing components and the grafting composition contains one or more hydrophilic reactive components.

7. The ophthalmic device of claim 1 that is in the form of a hydrogel and wherein the first reactive composition contains one or more hydrophilic reactive components and the grafting composition contains one or more silicone-containing components.

8. The ophthalmic device of claim 1 wherein the first reactive composition, the grafting composition, or both the first reactive composition and the grafting composition contain one or more additives selected from UV absorbers, photochromic compounds, pharmaceutical compounds, nutraceutical compounds, antimicrobial compounds, reactive tints, pigments, copolymerizable dyes, non-polymerizable dyes, release agents, wetting agents, and release agents.

9. The ophthalmic device of claim 1 selected from the group consisting of a contact lens, an intraocular lens, a punctal plug and an ocular insert.

10. The ophthalmic device of claim 1 wherein the process further comprises: following step (d), contacting the crosslinked substrate network with a second grafting composition containing one or more ethylenically unsaturated compounds and activating residual covalently bound activatable free radical initiator in the crosslinked substrate network such that the second grafting composition polymerizes therein with the crosslinked substrate network.

11. A process for making an ophthalmic device, the process comprising:
(a) providing a first reactive composition containing: (i) a bisacylphosphine oxide polymerization initiator (ii) one or more ethylenically unsaturated compounds; and (iii) a crosslinker;
(b) subjecting the first reactive composition to a first activation step such that the first reactive composition polymerizes therein to form a crosslinked substrate network containing a covalently bound activatable monoacylphosphine oxide free radical initiator;
(c) contacting the crosslinked substrate network with a grafting composition containing one or more ethylenically unsaturated compounds, wherein the contacting is conducted under conditions such that the grafting composition penetrates into the crosslinked substrate network; and
(d) activating the covalently bound activatable monoacylphosphine oxide free radical initiator of the crosslinked substrate network such that the grafting composition polymerizes therein with the crosslinked substrate network.

12. The process of claim 11 wherein the grafting composition of step (c) contains a crosslinker.

13. The process of claim 11 wherein the grafting composition of step (c) is free of a crosslinker.

14. The process of claim 11 wherein the one or more ethylenically unsaturated compounds of step (a) comprise one or more polymerizable groups independently selected from: (meth)acrylate, (meth)acrylamide, styryl, vinyl, N-vinyl lactam, N-vinylamide, O-vinylether, O-vinylcarbonate, O-vinylcarbamate, C 2-12 alkenyl, C 2-12 alkenylphenyl, C 2-12 alkenylnaphthyl, and C 2-6 alkenylphenyl-C 1-6 alkyl.

15. The process of claim 11 wherein the one or more ethylenically unsaturated compounds of step (c) comprise one or more polymerizable groups independently selected from: (meth)acrylate, (meth)acrylamide, styryl, vinyl, N-vinyl lactam, N-vinylamide, O-vinylether, O-vinylcarbonate, O-vinylcarbamate, C 2-12 alkenyl, C 2-12 alkenylphenyl, C 2-12 alkenylnaphthyl, and C 2-6 alkenylphenyl-C 1-6 alkyl.

16. The process of claim 11 that is in the form of a hydrogel and wherein the first reactive composition contains one or more silicone-containing components and the grafting composition contains one or more hydrophilic reactive components.

17. The process of claim 11 that is in the form of a hydrogel and wherein the first reactive composition contains one or more hydrophilic reactive components and the grafting composition contains one or more silicone-containing components.

18. The process of claim 11 wherein the first reactive composition, the grafting composition, or both the first reactive composition and the grafting composition contain one or more additives selected from UV absorbers, photochromic compounds, pharmaceutical compounds, nutraceutical compounds, antimicrobial compounds, reactive tints, pigments, copolymerizable dyes, non-polymerizable dyes, release agents, wetting agents, and release agents.

Assignees

• Johnson & Johnson Vision Care

Inventors

• Aitken Brian
• Scales Charles W
• Wood Joe M
• Widman Michael F

Classifications

• G02B1/043

  Contact lenses · CPC title

• G02C7/04

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

• C08L51/085

  on to polysiloxanes · CPC title

• C08F290/068 Primary

  Polysiloxanes · CPC title

• C08F222/102

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