Hydrogel from polysiloxane-containing urethane prepolymer, tris (trimethylsiloxy) silylpropyl methacrylate, and a hydrophilic comonomer

• US 6,596,294 B2
• Filed: 09/19/2001
• Issued: 07/22/2003
• 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: Baccei, Louis J., Lai, Yu-Chin
• Primary Examiner(s): Naff, David M.
• Assistant Examiner(s): Ware, Deborah K.
• Application Number:
  US09/956,415
• Publication Number:
  US 20020037271A1
• Time in Patent Office: 671 Days
• Field of Search: 435/41, 435/283.1, 424/422, 424/427, 424/423, 424/443, 424/486
• 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 polyurethane based prepolymer is provided and useful in biomedical devices which provides high oxygen permeability and superior physical properties. A hydrogel is produced from a comonomer mixture containing a polysiloxane-containing urethane prepolymer, tris(trimethylsiloxy)-silylpropyl methacrylate and a hydrophilic comonomer. The hydrogel is especially useful for biomedical materials such as contact lenses and implants.

Claims

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

(a) a polysiloxane-containing urethane prepolymer;

(b) tris(trimethylsiloxy)silylpropyl methacrylate; and

(c) a hydrophilic comonomer.

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 comonomer includes dimethylacrylamide.

4. The hydrogel material of claim 1, wherein the hydrophilic comonomer is selected from the group consisting of 2-hydroxyethyl methacrylate, N-vinyl-2-pyrrolidinone, methacrylic acid, dimethylacrylamide, and glycerol methacrylate.

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

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

.

7. The hydrogel material of claim 6, 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.

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

.

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

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

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

radicals are formed from 2-hydroxyethylmethyacrylate.

12. The hydrogel material of claim 8, 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 comonomer.