Surface wettable silicone hydrogels

• US 5,358,995 A
• Filed: 05/15/1992
• Issued: 10/25/1994
• Est. Priority Date: 05/15/1992
• Status: Expired due to Term

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Lai, Yu-Chin, Valint, Paul L. Jr., Ruscio, Dominic V.
• Primary Examiner(s): Lipman, Bernard
• Application Number:
  US07/883,449
• Time in Patent Office: 893 Days
• Field of Search: 524/547, 525/100, 526/279
• US Class Current: 524/542
• CPC Class Codes: A61L 27/16 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/52 Hydrogels or hydrocolloids
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: C08L 51/08 grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: Y10T 428/31855 Of addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31909 Next to second addition polymer from unsaturated monomers

Abstract

A novel silicone-containing, hydrogel material is disclosed comprising an acrylic-capped polysiloxane prepolymer, polymerized with a bulky polysiloxanylalkyl (meth)acrylate monomer and at least one hydrophilic monomer.

Claims

1. A silicone-containing, hydrogel material formed from the polymerization product of a monomer mix comprising:

a) an acrylic-capped polysiloxane prepolymer represented by the formula;

##STR4## wherein;

A and A'"'"' are independently an ester or amide of an acrylic or a methacrylic acid;

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

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

a and b are independently 1 to 10;

b) a bulky polysiloxanylalkyl (meth)acrylate monomer represented by the formula;

##STR5## wherein;

X is O or N--R;

R is H or CH₃ ;

R₁₁ -R₁₉ are independently an alkyl, fluoroalkyl, alcohol, ether or fluoroether group having 1-10 carbons, or an aromatic group having 6-18 carbons; and

a is 1, or 3 to 10; and

c) at least one hydrophilic monomer.

2. The hydrogen of claim 1 wherein said acrylic-capped polysiloxane prepolymer is comprised of a repeating number of between from about 25 to about 200 dimethylsiloxy units.

3. The hydrogel of claim 1 wherein said acrylic-capped polysiloxane prepolymer is an α

,ω

-Bis(methacryloxy alkyl)dialkylsilylpolysiloxane.

4. The hydrogel of claim 1 wherein said acrylic-capped polysiloxane prepolymer is α

,ω

-Bis(methacryloxybutyl)dimethylsilylpolysiloxane.

5. The hydrogel of claim 1 wherein said bulky polysiloxanylalkyl (meth)acrylate monomer is selected from the group consisting of pentamethyldisiloxanylmethyl methacrylate, tris(trimethylsiloxy)methacryloxy propylsilane, phenyltetramethyldisiloxanylethyl acrylate, and methyldi(trimethylsiloxy)methacryloxymethylsilane.

6. The hydrogel of claim 1 wherein said bulky polysiloxanylalkyl (meth)acrylate monomer is methacryloxypropyl tris(trimethylsiloxy)silane.

7. The hydrogel of claim 1 wherein said hydrophilic monomer is a vinyl-containing hydrophilic monomer.

8. The hydrogel of claim 7 wherein said vinyl-containing hydrophilic monomer is selected from the group consisting of, N-vinyl-N-methyl acetamide, N-vinyl-acetamide, N-vinyl-N-methyl formamide, and N-vinyl formamide.

9. The hydrogel of claim 7 wherein said vinyl-containing hydrophilic monomer is an N-vinyl lactam.

10. The hydrogel of claim 7 wherein said vinyl-containing hydrophilic monomer is N-vinyl pyrrolidone.

11. The hydrogel of claim 1 wherein said hydrophilic monomer is an acrylic-containing monomer.

12. The hydrogel of claim 11 wherein said acrylic-type hydrophilic monomer is selected from the group consisting of N,N-dimethyl acrylamide, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxymethylacrylamide, methacrylic acid and acrylic acid.

13. The hydrogel of claim 1 wherein said hydrogel comprises both a vinyl-containing hydrophilic monomer and an acrylic-containing hydrophilic monomer.

14. The hydrogel of claim 1 wherein said hydrogel comprises at least one crosslinking agent.

15. The hydrogel of claim 1 wherein said hydrogel comprises α

,ω

-Bis(methacryloxyalkyl)polysiloxane polymerized with methacryloxypropyl tris(trimethylsiloxy) silane and N,N-dimethyl acrylamide.

16. The hydrogen of claim 1 wherein said hydrogel comprises α

,ω

-Bis(methacryloxyalkyl)polysiloxane polymerized with methacryloxypropyl tris(trimethylsiloxy)silane, N,N-dimethyl acrylamide, N-vinyl pyrrolidone and at least one crosslinking agent.

17. The hydrogel of claim 1 wherein the polysiloxane prepolymer and bulky polysiloxyanylalkyl (meth)acrylate monomer are present in the monomer mix in relative amounts represented by the ratio range of from about 11:

1 to about 1;

11.

18. The hydrogel of claim 1 wherein the polysiloxane prepolymer and bulky polysiloxyanylalkyl (meth)acrylate monomer are present in the monomer mix in relative amounts represented by the ratio range of from about 2:

1 to about 1;

8.

19. The hydrogel of claim 1 wherein the polysiloxane prepolymer and bulky polysiloxyanylalkyl (meth)acrylate monomer are present in the monomer mix in relative amounts represented by the ratio range of from about 1:

1 to about 1;

4.

20. The hydrogel of claim 1 wherein the monomer mix comprises a hydrophilic monomer in the amount of about 40 weight percent.

21. A silicone-containing, hydrogel material formed from the polymerization product of a monomer mix comprising:

a) an acrylic-capped polysiloxane prepolymer represented by the formula;

##STR6## wherein;

A and A'"'"' are independently an ester or amide of an acrylic or a methacrylic acid;

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

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

a and b are independently 1 to 10;

b) a bulky polysiloxanylalkyl (meth)acrylate monomer represented by the formula;

##STR7## wherein;

X is O or N--R;

R is H or CH₃ ;

R₁₁ -R₁₉ are independently an alkyl, fluoroalkyl, alcohol, ether or fluoroether group having 1-10 carbons, or an aromatic group having 6-18 carbons; and

a is 1, or 3 to 10; and

c) at least one hydrophilic monomer representing at least 30 to 60 weight percent of the monomer mix.