Amphiphilic siloxane-containing (meth)acrylamides and uses thereof

• US 9,097,840 B2
• Filed: 12/13/2013
• Issued: 08/04/2015
• Est. Priority Date: 12/14/2012
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Chang, Frank, Zhou, Jian S.
• Primary Examiner(s): Peng, Kuo-Liang
• Application Number:
  US14/105,334
• Publication Number:
  US 20140171539A1
• Time in Patent Office: 599 Days
• Field of Search: 526/279
• US Class Current: 1/1
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C08F 220/58 containing oxygen in addition to the carbonamido oxygen , e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
• CPC Class Codes: C08F 220/585 and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]
• CPC Class Codes: C08F 220/606 and containing other heteroatoms
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 33/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The invention provides an amphiphilic siloxane-containing (meth)acrylamide which comprises one sole (meth)acrylamido group, one sole tris(trimethylsiloxy)silyl group, and one polyethylene glycol segment which is either dangling polymer chain or a hydrophilic linker between the (meth)acrylamido group and the tris(trimethylsiloxy)silyl group. The present invention is also related to a polymer, an actinically-crosslinkable silicone-containing prepolymer, a silicone hydrogel polymeric material, or a silicone hydrogel contact lens, which comprises monomeric units derived from an amphiphilic siloxane-containing (meth)acrylamido group, one tris(trimethylsiloxy)silyl group of the invention. In addition, the invention provides a method for making silicone hydrogel contact lenses using a water-based lens-forming formulation comprising an amphiphilic siloxane-containing (meth)acrylamido group, one tris(trimethylsiloxy)silyl group of the invention and/or an actinically-crosslinkable silicone-containing prepolymer of the invention.

Claims

1. An amphiphilic siloxane-containing (meth)acrylamide, being represented by formula (1) or (2)

2. The amphiphilic siloxane-containing (meth)acrylamide of claim 1, being represented by formula (1) as defined in claim 1.

3. The amphiphilic siloxane-containing (meth)acrylamide of claim 2, wherein R′

is hydrogen;

R₁₀ is hydrogen or methyl;

R₁₁ is a linear or branched C₂-C₆ alkylene divalent radical;

R₁₂ is C₁-C₆ alkoxy;

Z₁ and Z₂ are a direct bond;

Z₃ is C₂-C₄ alkylene divalent radical;

X₁ is —

O—

CO—

NH—

or —

O—

CO—

NH—

R₁₃—

NH—

CO—

O—

in which R₁₃ is a linear or branched C₂-C₁₂ alkylene divalent radical or a C₅-C₄₅ cycloaliphatic or aliphatic-cycloaliphatic divalent radical;

q1 is an integer from 2 to 50.

4. The amphiphilic siloxane-containing (meth)acrylamide of claim 1, being represented by formula (2) as defined in claim 1.

5. The amphiphilic siloxane-containing (meth)acrylamide of claim 4, being represented by any one of formula (2a) to (2d)

6. The amphiphilic siloxane-containing (meth)acrylamide of claim 1, wherein the amphiphilic siloxane-containing (meth)acrylamide has a water solubility or dispersibility of at least about 5% by weight in water.

7. A polymer comprising monomeric units derived from an amphiphilic siloxane-containing (meth)acrylamide of claim 1.

8. The polymer of claim 7, wherein the polymer is an actinically-crosslinkable silicone-containing prepolymer which further comprises:

(1) crosslinking units derived from at least one polysiloxane-containing crosslinker and/or at least one non-silicone crosslinker;

(2) hydrophilic units derived from at least one hydrophilic vinylic monomer;

(3) polymerizable units derived from a chain transfer agent having a first reactive functional group other than thiol group and/or a vinylic monomer having a second reactive functional group other than ethylenically-unsaturated group, wherein the polymerizable units each comprise an ethylenically unsaturated group covalently attached to one polymerizable unit through the first or second reactive functional group; and

(4) optionally UV-absorbing units derived from a UV-absorbing vinylic monomer, wherein the prepolymer is capable of being actinically crosslinked, in the absence of one or more vinylic monomers, to form a silicone hydrogel contact lens having a water content of from about 20% to about 75% by weight when fully hydrated, and an oxygen permeability (Dk) of at least about 40 barrers.

9. The polymer of claim 8, wherein the prepolymer has a high water solubility or dispersibility of at least about 5% by weight in water, wherein the crosslinking units are derived from at least one hydrophilized polysiloxane-containing crosslinker and/or at least one non-silicone hydrophilic crosslinker.

10. A soft contact lens comprising a silicone hydrogel material comprising monomeric units derived from a hydrophilic vinylic monomer and monomeric units derived from an amphiphilic siloxane-containing (meth)acrylamide of claim 1, wherein the contact lens has a water content of from about 20% to about 75% by weight when fully hydrated, an oxygen permeability (Dk) of at least about 40 barrers, and an elastic modulus of from about 0.1 MPa to about 2.0 MPa.

11. A soft contact lens comprising a silicone hydrogel material obtained by curing a lens-forming material in a mold, wherein the lens-forming formulation comprises at least one hydrophilic vinylic monomer and at least one amphiphilic siloxane-containing (meth)acrylamide of claim 1, wherein the contact lens has a water content of from about 20% to about 75% by weight when fully hydrated, an oxygen permeability (Dk) of at least about 40 barrers, and an elastic modulus of from about 0.1 MPa to about 2.0 MPa.

12. The soft contact lens of claim 11, wherein the lens-forming formulation further comprises one or more components selected from the group consisting of a polysiloxane-containing crosslinker, a non-silicone crosslinker, a photoinitiator, a thermal initiator, a UV-absorbing vinylic monomer, a visibility tinting agent, antimicrobial agents, a bioactive agent, leachable lubricants, leachable tear-stabilizing agents, and mixtures thereof.

13. A soft contact lens comprising a silicone hydrogel material obtained by curing a lens-forming material in a mold, wherein the lens-forming formulation comprises at least one actinically-crosslinkable silicone-containing prepolymer of claim 8, wherein the contact lens has a water content of from about 20% to about 75% by weight when fully hydrated, an oxygen permeability (Dk) of at least about 40 barrers, and an elastic modulus of from about 0.1 MPa to about 2.0 MPa.

14. The soft contact lens of claim 13, wherein the lens-forming formulation further comprises one or more components selected from the group consisting of a polysiloxane-containing crosslinker, a non-silicone crosslinker, a photoinitiator, a thermal initiator, a UV-absorbing vinylic monomer, a visibility tinting agent, antimicrobial agents, a bioactive agent, leachable lubricants, leachable tear-stabilizing agents, and mixtures thereof.