Polymer compositions containing grafted polymeric networks and processes for their preparation and use

Patent metadata

Field	Value
Publication number	US-11021558-B2
Application number	US-201715656033-A
Country	US
Kind code	B2
Filing date	Jul 21, 2017
Priority date	Aug 5, 2016
Publication date	Jun 1, 2021
Grant date	Jun 1, 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) combining the crosslinked substrate network with a second reactive composition containing one or more ethylenically unsaturated compounds; and (d) activating the covalently bound activatable free radical initiator of the crosslinked substrate network such that the second reactive composition polymerizes therein with the crosslinked substrate network to form a grafted polymeric network and a byproduct polymer. Also provided are precursors to the polymer compositions, processes for preparation of the polymer compositions, and methods of using the polymer compositions, for instance in medical devices.

First claim

We claim:

1. A polymer composition 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 monacylphosphine oxide free radical initiator, wherein the first activation step is conducted by irradiating the bisacylphosphine oxide with light consisting essentially of wavelengths of at least 420 nm;
(c) combining the crosslinked substrate network with a second reactive composition containing one or more ethylenically unsaturated compounds; and
(d) activating the covalently bound monacylphosphine oxide of the crosslinked substrate network such that the second reactive composition polymerizes therein with the crosslinked substrate network to form a grafted polymeric network and a byproduct polymer.

2. The polymer composition of claim 1 wherein step (d) is conducted in the presence of a crosslinker such that the byproduct polymer is covalently bound with the grafted polymeric network.

3. The polymer composition of claim 1 wherein step (d) is conducted in the substantial absence of a crosslinker such that at least a portion of the byproduct polymer is not covalently bound to the grafted polymeric network.

4. The polymer composition of claim 1 wherein the one or more ethylenically unsaturated compounds of step (a) comprise one or more reactive 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 polymer composition of claim 1 wherein the one or more ethylenically unsaturated compounds of step (c) comprise one or more reactive 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 polymer composition of claim 1 that is in the form of a hydrogel and wherein the first reactive composition contains silicone reactive components and the second reactive composition contains hydrophilic reactive components.

7. The polymer composition of claim 1 that is in the form of a hydrogel and wherein the first reactive composition contains hydrophilic reactive components and the second reactive composition contains silicone reactive components.

8. The polymer composition of claim 1 wherein the first reactive composition further comprises one or more of a polyamide, a UV-VIS absorber, a dye, a tint, a pigment, an antimicrobial, a pharmaceutical, and a nutraceutical.

9. The polymer composition of claim 1 wherein the second reactive composition further comprises one or more of a polyamide, a UV-VIS absorber, a dye, a tint, a pigment, an antimicrobial, a pharmaceutical, and a nutraceutical.

10. A medical device comprising the polymer composition of claim 1 .

11. An ophthalmic device comprising the polymer composition of claim 1 .

12. The ophthalmic device of claim 11 selected from the group consisting of a contact lens, an intraocular lens, a punctal plug and an ocular insert.

13. A contact lens comprising a polymer composition, wherein the polymer composition is formed by the process of claim 1 .

14. The contact lens of claim 13 wherein the first reactive composition, the second reactive composition, or both the first reactive composition and the second reactive 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
• Joslin Scott
• Zhang Yong
• Sinha Dola
• Mahadevan Shivkumar
• Martin Patricia
• Lu Fang
• Duis Donnie
• Arnold Stephen C

Classifications

• C08F290/068 Primary

  Polysiloxanes · CPC title

• C08F283/124 Primary

  on to polysiloxanes having carbon-to-carbon double bonds · CPC title

• C08J7/16

  with polymerisable compounds · CPC title

• G02C7/04

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

• C08F283/12

  on to polysiloxanes · CPC title