Prepolymers useful in biomedical devices

• US 6,312,706 B1
• Filed: 01/26/2000
• Issued: 11/06/2001
• Est. Priority Date: 06/07/1989
• Status: Expired due to Fees

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Lai, Yu-Chi, Baccei, Louis J.
• Primary Examiner(s): Page, Thurman K.
• Assistant Examiner(s): WARE, TODD
• Application Number:
  US09/491,983
• Time in Patent Office: 650 Days
• Field of Search: 424/422, 424/427, 424/429, 514/912, 351/160.H, 351/160.R
• US Class Current: 424/422
• CPC Class Codes: A61F 2/14 Eye parts, e.g. lenses, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08F 299/06 from polyurethanes
• CPC Class Codes: C08G 18/28 characterised by the compounds used containing active hydrogen
• CPC Class Codes: C08G 18/48 Polyethers
• CPC Class Codes: C08G 18/50 having heteroatoms other than oxygen
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/6674 with compounds of group C08G18/3203
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 77/458 containing polyurethane sequences
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: G02C 7/04 Contact lenses for the eyes disinfection or sterilisation of contact lenses A61L12/00

Abstract

A novel polyurethane based prepolymer useful in biomedical devices which provides high oxygen permeability and superior physical properties.

Claims

1. A hydrogel material that is the polymerization product of a comonomer mixture comprising:

(a) a polysiloxane-containing urethane prepolymer endcapped with polymerizable ethylenically unsaturated organic radicals, wherein the polymerizable unsaturated organic radicals comprise radicals represented by the general chemical formula;

 

wherein

R¹ denotes a divalent alkylene radical with 1 to 10 carbon atoms;

R² denotes a —

H or —

CH₃ radical;

R³ denotes a —

H radical or an alkyl radical with 1 to 6 carbon atoms or a —

COY—

R⁴ radical where Y is —

O—

, —

S—

or —

NH— and

R⁴ denotes an alkyl radical with 1 to 12 carbon atoms;

Z is —

O—

or —

NH—

;

X denotes —

CO—

or —

OCO—

;

Ar denotes an aromatic radical with 6 to 30 carbon atoms;

w is 0 to 6;

x is 0 or 1;

y is 0 or 1; and

z is 0 or 1;

(b) tris(trimethylsiloxy)silylpropyl methacrylate in an amount effective to improve percent elongation of the hydrogel material; and

(c) a hydrophilic comonomer selected from the group consisting of N-vinyl-2-pyrrolidinone, N,N-dimethylacrylamide, and mixtures thereof,

said hydrogel material having oxygen permeability and mechanical properties suitable for hydrogel contact lens applications, and a water content of at least about 20 weight percent.

2. The hydrogel material of claim 1, wherein the comonomer mixture comprises:

(a) 30 to 90 weight percent of the polysiloxane-containing urethane prepolymer;

(b) 1 to 30 weight percent of tris(trimethylsiloxy)silylpropyl methacrylate; and

(c) 20-40 weight percent of the hydrophilic monomer.

3. The hydrogel material of claim 2, wherein the hydrophilic monomer includes dimethylacrylamide.

4. The hydrogel material of claim 1, wherein the polysiloxane-containing urethane prepolymer is described by the general chemical formulae

5. The hydrogel material of claim 4, wherein said prepolymer has the formula E(*D*A*D*G)_a*D*A*D*E′

.

6. The hydrogel material of claim 5, wherein the G radical is formed from neopentyl glycol, the D radical is formed from isophorone diisocyanate, and the E and E′

radicals are each formed from 2-hydroxyethylmethyacrylate.

7. The hydrogel material of claim 4, wherein said prepolymer has the formula E(*D*G*D*A)_a*D*G*D*E′

.

8. The hydrogel material of claim 7, wherein the D radical is formed from isophorone diisocyanate.

9. The hydrogel material of claim 8, wherein the G radical is formed from neopentyl glycol, diethylene glycol or 1,4-butanediol.

10. The hydrogel material of claim 9, wherein the E and E′

radicals are formed from 2-hydroxyethylmethyacrylate.

11. The hydrogel material of claim 7, wherein the comonomer mixture comprises:

(a) 30 to 90 weight percent of the polysiloxane-containing urethaneprepolymer;

(b) 1 to 30 weight percent of tris(trimethylsiloxy)silylpropyl methacrylate; and

(c) 20-40 weight percent of the hydrophilic monomer.

12. The hydrogel material of claim 1, which has a water content of at least 22.4 weight percent.