Organic compounds

• US 7,521,519 B1
• Filed: 03/14/2000
• Issued: 04/21/2009
• Est. Priority Date: 03/14/2000
• Status: Expired due to Fees

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Schremmer, Jacalyn Marie, Holland, Troy Vernon, Hirt, Thomas, Lohmann, Dieter
• Primary Examiner(s): Dawson; Robert
• Assistant Examiner(s): PENG, KUO LIANG
• Application Number:
  US09/525,158
• Time in Patent Office: 3,325 Days
• Field of Search: 523/107, 528/33, 528/26, 528/29, 528/25, 528/32, 568/615
• US Class Current: 528/33
• 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 molding, for example ophthalmic moldings such as in particular contact lenses.

Claims

1. An amphiphilic block copolymer of formula

2. An amphiphilic block copolymer according to claim 1 of formula

3. An amphiphilic block copolymer according to claim 1 of formula

(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.

4. An amphiphilic block copolymer according to claim 1, wherein A is a polysiloxane segment of formula

5. An amphiphilic block copolymer according to 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-C₈-cycloalkylene or C₁-C₆-alkylene-C₃-C₈-cycloalkylene-C₁-C₆-alkylene.

6. An amphiphilic block copolymer according to claim 5, 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).

7. An amphiphilic block copolymer according to claim 1, wherein B is a non-ionic segment selected from the group consisting of a polyoxyalkylene, polysaccharide, polypeptide, poly(vinylpyrrolidone), polyalkylacrylate, polymethacrylate, polyhydroxyalkylacrylate, polyhydroxymethacrylate, polyacryl alkylene imine, polyacryl amide, polyvinyl alcohol, polyvinyl ether and a polyol, or B is a polyionic segment selected from the group consisting of a polyallylammonium, polyethyleneimine, polyvinylbenzyltrimethylammonium, polyaniline, sulfonated polyaniline, polypyrrole, polypyridinium segment, polyacrylic acid, polymethacrylic acid, a polythiophene-acetic acid, a polystyrenesulfonic acid and a zwitterionic segment, or a salt thereof.

8. An amphiphilic block copolymer according to claim 1, wherein Q is a radical Q₁ of formula

9. An amphiphilic block copolymer according to claim 1, wherein Q is a polyoxyalkylene, poly(vinylpyrrolidone), poly(hydroxyethylacrylate), poly(hydroxyethylmeth-acrylate), 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.

10. An amphiphilic block copolymer according to claim 9, wherein Q is a hydrophilic segment of formula

—

((alk″

)—

O)_c—

[(CH₂—

CH₂—

O)_a—

(CHR₆—

CHR₇—

O)_b]—

(alk″

)—

L₁′

—

Q₂  

 

(5a)

11. An amphiphilic block copolymer according to claim 2 of formula (1a), wherein A is a polysiloxane segment of formula

12. An amphiphillic block copolymer according to claim 3 of formula (1b), wehrein A,B, L₁, L₂ and Q are defined in claim 11, and p and q are each independently of the other an integer of 2 to 15.