POLYSILOXANE COPOLYMERS WITH TERMINAL HYDROPHILIC POLYMER CHAINS

• US 20100120938A1
• Filed: 11/11/2009
• Published: 05/13/2010
• Est. Priority Date: 11/13/2008
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Phelan, John Christopher, Winterton, Lynn Cook, Qiu, Yongxing, Scott, Robert
• Granted Patent: US 8,048,968 B2
• Time in Patent Office: Days
• US Class Current: 523/107
• CPC Class Codes: C08F 293/00 Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule on to polymers modified by introduction of unsaturated end groups C08F290/02
• CPC Class Codes: C08F 299/08 from polysiloxanes
• CPC Class Codes: C08G 77/442 containing vinyl polymer sequences
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The invention provides an actinically-crosslinkable linear polysiloxane copolymer. The actinically-crosslinkable polysiloxane copolymer can be used to prepare a silicone hydrogel contact lens having a hydrophilic surface without post-curing surface treatment. The invention is also related to a silicone hydrogel contact lens obtained from a lens-forming material including an actinically-crosslinkable polysiloxane copolymer of the invention and to a method for making an actinically-crosslinkable polysiloxane copolymer of the invention. In addition, the invention provides a non-crosslinkable linear polysiloxane copolymer capable of being used as a internal wetting agent which can render the surface of a silicone hydrogel contact lens hydrophilic.

Claims

1. An actinically-crosslinkable linear polysiloxane copolymer, comprising at least one linear polysiloxane segment end-capped at least at one of the two ends of the polysiloxane segment with one hydrophilic polymer chain through a linkage and at least one ethylenically unsaturated group covalently linked to the linkage, wherein the hydrophilic chains is composed of one or more monomer units selected from the group consisting of units of N-vinyl-2-pyrrolidone (NVP), N,N-dimethylacrylamide (DMA), dimethylaminoethyl methacrylate, dimethylaminoethyl acrylate, vinyl alcohol, dimethylaminoethylmethacrylamide, a C₁-C₄-alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of from 200 to 1500, N-vinyl-N-methyl isopropylamide, N-vinyl-N-methyl acetamide, and mixtures thereof.

2. The polysiloxane copolymer of claim 1, being defined by formula (I)

3. The polysiloxane copolymer of claim 2, wherein Q is an ethylenically unsaturated group of formula (VI)

4. The polysiloxane copolymer of claim 3, wherein T is a monovalent hydrophilic polymer chain comprising units of N-vinyl-2-pyrrolidone (NVP).

5. The polysiloxane copolymer of claim 3, wherein T is a monovalent hydrophilic polymer chain comprising units of N,N-dimethylacrylamide (DMA), dimethylaminoethyl methacrylate, dimethylaminoethyl acrylate, and/or dimethylaminoethylmethacrylamide.

6. The polysiloxane copolymer of claim 3, wherein T is a monovalent hydrophilic polymer chain comprising units of a C₁-C₄-alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of from 200 to 1500.

7. The polysiloxane copolymer of claim 3, wherein T is a monovalent hydrophilic polymer chain comprising units of N-vinyl-N-methyl isopropylamide, N-vinyl-N-methyl acetamide.

8. The polysiloxane copolymer of claim 3, wherein T is a monovalent hydrophilic polymer chain comprising units of vinyl alcohol.

9. A silicone hydrogel contact lens, comprising:

a silicone hydrogel material and dangling hydrophilic polymer chains which are covalently anchored to the polymer matrix of the silicone hydrogel material, wherein the silicone hydrogel material is obtained by polymerizing a lens-forming material including an actinically-crosslinkable linear polysiloxane copolymer, wherein the actinically-crosslinkable linear polysiloxane copolymer comprises at least one linear polysiloxane segment end-capped at least at one of the two ends of the polysiloxane segment with a hydrophilic polymer chain through a linkage and at least one ethylenically unsaturated group covalently linked to the linkage, wherein the dangling hydrophilic polymer chains are derived from the actinically-crosslinkable polysiloxane copolymer, wherein the dangling hydrophilic polymer chains in the silicone hydrogel material is capable of imparting the silicone hydrogel contact lens a hydrophilic surface without post-curing surface treatment.

10. The silicone hydrogel contact lens of claim 9, wherein the actinically-crosslinkable linear polysiloxane copolymer is defined by formula (I)

11. The silicone hydrogel contact lens of claim 10, wherein Q is an ethylenically unsaturated group of formula (VI)

12. The silicone hydrogel contact lens of claim 11, wherein the silicone hydrogel lens-forming material further comprises at least one component selected from the group consisting of a silicone-containing vinylic monomer, a silicone-containing macromer, a silicone-containing prepolymer, a hydrophilic vinylic monomer, a hydrophobic vinylic monomer, a hydrophilic prepolymer, a cross-linking agents, an antimicrobial agent, a chain transfer agent, radical initiator, UV-absorbers, inhibitors, fillers, visibility tinting agents, a bioactive agent, a leachable lubricant, and combination thereof.

13. The silicone hydrogel contact lens of claim 12, wherein the contact lens has at least one property selected from the group consisting of an oxygen permeability of at least about 35 barrers, an Ionoflux Diffusion Coefficient, D, of at least about 1.5×

10<sup>−

6</sup> mm²/min, an elastic modulus of from about 0.3 MPa to about 1.5 MPa, a water content of preferably from about 15% to about 60%, an averaged water contact angle of about 70 degrees or less, and a combination thereof.

14. The silicone hydrogel contact lens of claim 12, wherein T is a monovalent hydrophilic polymer chain comprising units of N-vinyl-2-pyrrolidone (NVP).

15. The silicone hydrogel contact lens of claim 12, wherein T is a monovalent hydrophilic polymer chain comprising units of N,N-dimethylacrylamide (DMA), dimethylaminoethyl methacrylate, dimethylaminoethyl acrylate, and/or dimethylaminoethylmethacrylamide.

16. The silicone hydrogel contact lens of claim 12, wherein T is a monovalent hydrophilic polymer chain comprising units of a C₁-C₄-alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of from 200 to 1500.

17. The silicone hydrogel contact lens of claim 12, wherein T is a monovalent hydrophilic polymer chain comprising units of N-vinyl-N-methyl isopropylamide, N-vinyl-N-methyl acetamide.

18. The silicone hydrogel contact lens of claim 12, wherein T is a monovalent hydrophilic polymer chain comprising units of vinyl alcohol.

19. A non-crosslinkable polysiloxane copolymer, comprising a polysiloxane segment end-capped at both ends each with one hydrophilic polymer chain, wherein the non-crosslinkable polysiloxane copolymer is free of ethylenically unsaturated group and defined by formula (VIII)