Organic compounds

• US 7,956,135 B2
• Filed: 01/21/2009
• Issued: 06/07/2011
• Est. Priority Date: 03/14/2000
• Status: Expired due to Fees

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Schremmer, Jacalyn Marie, Hirt, Thomas, Lohmann, Dieter, Holland, Troy Vernon
• Primary Examiner(s): PENG, KUO LIANG
• Application Number:
  US12/321,442
• Publication Number:
  US 20090137737A1
• Time in Patent Office: 867 Days
• Field of Search: 525/474, 568/615, 523/107
• US Class Current: 525/474
• CPC Class Codes: C08G 77/42 Block-or graft-polymers containing polysiloxane sequences polymerising aliphatic unsaturated monomers on to a polysiloxane C08F283/12

Abstract

The invention relates to novel crosslinkable copolymers of formula

wherein the variables are as defined in the claims. The copolymers of the invention are especially useful for the manufacture of biomedical moldings, for example ophthalmic moldings such as in particular contact lenses.

Claims

1. A process for the manufacture of a molding, which comprises crosslinking an amphiphilic block copolymer of formula (1) in a mold

2. A process according to claim 1 wherein the molding is an ophthalmic molding and wherein the block copolymer is photo-crosslinked in an ophthalmic mold using actinic radiation.

3. A molding obtained by the process according to claim 1.

4. A molding according to claim 3, which is an ophthalmic molding, intraocular lens, or artificial cornea.

5. A molding according to claim 3, which is a contact lens.

6. The process of claim 1, wherein t is the number 2, p and q is the number zero, wherein the amphiphilic block copolymer is defined by formula (1a)

7. The process of claim 1, wherein t is the number zero, wherein the amphiphilic block copolymer is defined by formula (1b)

(B-L₂)_q-A-(L₁-Q)_p 

 

(1b),

wherein A, B, L₁, L₂ and Q are each as defined in claim 1, and p and q are each independently of the other an integer from 2 to 20.

8. The process of claim 1, wherein A is a polysiloxane segment of formula

9. The process of claim 1, wherein L₁, L₂ and L₃ are each independently of the other a bivalent linking group of formula

—

X₁—

C(O)—

NH—

R₁₀—

NH—

C(O)—

X₂—

 

 

(4a),

—

X₁—

C(O)—

R₁₀—

C(O)—

X₂—

 

 

(4b),

—

X₁—

C(O)—

 

 

(4c),

—

C(O)—

X₂—

 

 

(4d), or

—

X₁—

C(O)—

X₂—

 

 

(4e),

wherein X₁ and X₂ are each independently of the other a group —

O—

, —

S—

or —

NR₀—

, R₀ is hydrogen or C₁-C₄-alkyl, and R₁₀ is linear or branched C₁-C₁₈-alkylene or unsubstituted or C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₆-C₁₀-arylene, C₇-C₁₈-aralkylene, C₆-C₁₀-arylene-C₁-C₂-alkylene-C₆-C₁₀-arylene, C₃-C₈-cycloalkylene, C₃-C₈-cycloalkylene-C₁-C₆-alkylene, C₃-C₈-cycloalkylene-C₁-C₂-alkylene-C₃-C_o-cycloalkylene or C₁-C₆-alkylene-C₃-C₈-cycloalkylene-C₁-C₆-alkylene.

10. The process of claim 1, wherein L₁ is a linking group of formula (4a), (4c) or (4e), L₂ is a linking group of formula (4a), and L₃ is a linking group of formula (4b) or (4c).

11. The process of claim 1, wherein B is a non-ionic segment selected from the group consisting of polysaccharide, polypeptide, poly(vinylpyrrolidone), polyhydroxyalkylacrylate, polyhydroxyalkylmethacrylate, polyacyl alkylene imine, polyacryl amide, polyvinyl alcohol, polyvinyl ether and a polyol.

12. The process of claim 1, wherein Q is a radical Q₁ of formula

13. The process of claim 1, wherein Q is a polyoxyalkylene, poly(vinylpyrrolidone), poly(hydroxyethylacrylate), poly(hydroxyethylmethacrylate), polyacrylamide, poly(N,N-dimethylacrylamide), polyacrylic acid, polymethacrylic acid, polyacyl alkylene imine or a copolymeric mixture of two or more of the above-mentioned polymers which in each case comprises one or more ethylenically unsaturated bond and has a weight average molecular weight of ≧

100.

14. The process of claim 13, wherein Q is a hydrophilic segment of formula

15. The process of claim 6, wherein A is a polysiloxane segment of formula

16. The process of claim 7, wherein

p and q are each independently of the other an integer 2 to 15,

A is a polysiloxane segment of formula