Contact lens material

• US 6,762,264 B2
• Filed: 11/12/2002
• Issued: 07/13/2004
• Est. Priority Date: 07/27/1999
• Status: Expired due to Term

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Künzler, Jay F., Martin, Arthur W.
• Primary Examiner(s): Moore, Margaret G.
• Application Number:
  US10/293,056
• Publication Number:
  US 20030109637A1
• Time in Patent Office: 609 Days
• Field of Search: 526/279, 528/32, 351/160.H, 623/656, 623/659
• US Class Current: 526/279
• CPC Class Codes: C08F 283/12 on to polysiloxanes
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08G 77/06 Preparatory processes C08G77/045 takes precedence
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A method for reducing the modulus of polymer silicone hydrogel compositions by employing monomeric polysiloxanes endcapped with trimethylsilyl to reduce the crosslinking density of the hydrogel. The synthesis consists of a single vessel acid catalyzed ring opening polymerization and may be employed to produce copolymers useful as hydrogel contact lens materials.

Claims

1. A hydrogel formed from the polymerization product of a monomer mixture comprising:

(a) a mixture of polysiloxane prepolymers represented by formulae (I) and (II);

 

wherein;

each A and A′

is an activated unsaturated radical;

A″

is an alkyl group;

each R₁-R₁₀ is independently an alkyl, fluoroalkyl, alcohol, ether, or fluoroether group having 1-10 carbons, or an aromatic group having 6-18 carbons;

each m, n, and p are independently 0 to 200, m+n+p being from about 23 to 200;

each a is 1 to 10; and

each b is 0to 10; and

(b) a hydrophilic monomer,

wherein the monomer mixture further comprises a monofunctional, ethylenically unsaturated silicone-containing monomer represented by the formula;

 

wherein;

X denotes —

COO—

, —

CONR⁴—

, —

OCOO—

, or —

OCONR⁴—

where each R⁴ is independently H or lower alkyl;

R³ denotes hydrogen or methyl;

h is 1 to 10; and

each R² independently denotes a lower alkyl radical, a phenyl radical or a radical of the formula

2. The hydrogel of claim 1, said monofunctional, ethylenically unsaturated silicone-containing monomer includes methacryloxypropyl tris(trimethylsiloxy)silane.

3. The hydrogel of claim 1, wherein the hydrophilic monomer includes an acrylic-containing monomer.

4. The hydrogel of claim 3, wherein the hydrophilic monomer includes N,N-dimethyl acrylamide.

5. The hydrogel of claim 1, wherein the hydrophilic monomer includes a vinyl-containing monomer.

6. The hydrogel of claim 5, wherein said hydrophilic monomer includes N-vinyl pyrrolidone.

7. The hydrogel of claim 1, wherein the hydrophilic monomer includes at least one member selected from the group consisting of N,N-dimethylarcylamide and N-vinyl pyrrolidone.

8. The hydrogel of claim 1, wherein in Formulae (I) and (II), each A and A′

is a readical represented by the formula;

wherein X is hydrogen or methyl, and Y is —

O—

or —

NH—

.

9. The hydrogel of claim 8, wherein A″

is methyl.

10. The hydrogel of claim 8, wherein in Formulae (I) and (II), each R₁-R₁₀ is an alkyl or a fluoroalkyl group.

11. The hydrogel of claim 10, wherein in Formulae (I) and (II), each R₁-R¹⁰ is methyl.

12. The hydrogel of claim 10, wherein in Formulae (I) and (II), each m+n+p is within the range of 25 to 50.

13. The hydrogel of claim 10, wherein the prepolymer of Formula (ii) is present at 1 to 70 mole % based on total mole % of the Formulae (I) and (II) prepolymers.

14. The hydrogel of claim 13, wherein the prepolymer of Formula (II) is present at 25 to 50 mole % based on total mole % of the Formulae (I) and (II) prepolymers.

15. The hydrogel of claim 14, wherein the prepolymer of Formula (II) is present at 40 to 50 mole % based on total mole % of the Formulae (I) and (II) prepolymers.

16. A contact lens comprising the hydrogel of claim 1.

17. An intraocular lens comprising the hydrogel of claim 1.

18. A method of making a hydrogel, comprising:

(a) reacting a a cyclic siloxane and a dimethacrylate disiloxane in the presence of a catalyst and a disiloxane having the formula;

 

wherein R₁₁-R¹⁶ are independently an alkyl group having 1-5 carbons, to form a mixture of polysiloxane prepolymers represented by formulae (I) and (II);

 

wherein;

each A and A′

is an acitvated unsaturated radical;

A″

is an alkyl group;

each R₁-R₁₀ is independently an alkyl, fluoroalkyl, alcohol, ether, or fluoroether group having 1-10 carbons, or an aromatic group having 6-18 carbons;

each m, n, and p are independently 0 to 200, m+n+p being from about 23 to 200;

each a is 1 to 10; and

each b is 0 to 10; and

(b) polymerizing a hydrophilic monomer with said mixture of polysiloxane prepolymers represented by formulae (I) and (II).