Amphiphilic siloxane-containing vinylic monomers and uses thereof

• US 9,103,965 B2
• Filed: 12/13/2013
• Issued: 08/11/2015
• Est. Priority Date: 12/14/2012
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Chang, Frank
• Primary Examiner(s): Yoon, Tae H
• Application Number:
  US14/105,275
• Publication Number:
  US 20140171542A1
• Time in Patent Office: 606 Days
• Field of Search: 523/107, 556/420, 556/437
• US Class Current: 1/1
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• 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: C07F 7/089 Treatments not covered by a preceding group
• CPC Class Codes: C08F 30/08 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 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The invention provides an amphiphilic siloxane-containing vinylic monomer which comprises one sole ethylenically unsaturated group and a siloxane-containing group covalently linked to the ethylenically-unsaturated group through a hydrophilic linker. 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 vinylic monomer 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 vinylic monomer of the invention and/or an actinically-crosslinkable silicone-containing prepolymer of the invention.

Claims

1. An amphiphilic siloxane-containing vinylic monomer, comprising:

one sole ethylenically unsaturated group (Q), one sole bulky siloxane-containing group BSi, and one hydrophilic linkage (hL) between Q and BSi, wherein the amphiphilic siloxane-containing vinylic monomer is represented by formula (I)

Q-X₁-hL-X₂—

BSi 

 

(I)

In which;

Q is an ethylenically unsaturated group of formula (II)

2. The amphiphilic siloxane-containing vinylic monomer of claim 1, wherein Q is

3. The amphiphilic siloxane-containing vinylic monomer of claim 2, wherein BSi is a monovalent radical of formula (1A) in which A1, A2 and A3 is a radical of formula (2).

4. The amphiphilic siloxane-containing vinylic monomer of claim 2, wherein BSi is a monovalent radical of formula (1B) in which B₁ and B₂ independent of each other are C₁-C₆ alkyl.

5. The amphiphilic siloxane-containing vinylic monomer of claim 2, wherein hL in formula (I) is an oligomeric polyoxazoline segment.

6. The amphiphilic siloxane-containing vinylic monomer of claim 2, wherein hL in formula (I) is an oligomeric polypeptide segment composed of at least one amino acid selected from the group consisting of asparagine, glutamine, alanine, glycine, and combinations thereof.

7. The amphiphilic siloxane-containing vinylic monomer of claim 2, wherein hL in formula (I) is a hydrophilic polymer segment composed of monomeric units derived from at least one hydrophilic vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl(meth)acrylamide, dimethylaminoethyl(meth)acrylate, dimethylaminoethyl(meth)acrylamide, N-vinyl-2-pyrrolidone, N-vinyl-N-methyl isopropylamide, N-vinyl-N-methyl acetamide, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, N-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 1-n-propyl-3-methylene-2-pyrrolidone, 1-n-propyl-5-methylene-2-pyrrolidone, 1-isopropyl-3-methylene-2-pyrrolidone, 1-isopropyl-5-methylene-2-pyrrolidone, 1-n-butyl-3-methylene-2-pyrrolidone, 1-tert-butyl-3-methylene-2-pyrrolidone, and mixtures thereof.

8. The amphiphilic siloxane-containing vinylic monomer of claim 7, wherein hL in formula (I) is a hydrophilic polymer segment composed of monomeric units derived from at least one hydrophilic vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl(meth)acrylamide, dimethylaminoethyl(meth)acrylate, dimethylaminoethyl(meth)acrylamide, N-vinyl-2-pyrrolidone, N-vinyl-N-methyl acetamide, N-vinyl acetamide, N-methyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, and mixtures thereof.

9. The amphiphilic siloxane-containing vinylic monomer of claim 2, wherein the amphiphilic siloxane-containing vinylic monomer has a water solubility or dispersibility of at least about 5% by weight in water.