Surface wettable silicone hydrogels

• US 5,387,632 A
• Filed: 08/03/1994
• Issued: 02/07/1995
• 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:
  US08/285,473
• Time in Patent Office: 188 Days
• Field of Search: 428/500, 526/279, 524/547
• US Class Current: 526/279
• 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 contact lens made from 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 with m+n+p being from 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 contact lens of claim 1 wherein said acrylic ester-capped polysiloxane prepolymer is comprised of a repeating number of between from about 2 to about 200 dimethylsiloxy units.

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

,ω

-Bis(methacryloxyalkyl)dialkylsilyl polysiloxane.

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

,ω

-Bis(methacryloxybutyl)dimethylsilylpolysiloxane.

5. The contact lens 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 contact lens of claim 1 wherein said bulky polysiloxanylalkyl (meth)acrylate monomer is methacryloxypropyl tris(trimethylsiloxy)silane.

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

8. The contact lens 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 contact lens of claim 7 wherein said vinyl-containing hydrophilic monomer is an N-vinyl lactam.

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

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

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

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

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

,ω

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

16. The contact lens of claim 1 wherein said hydrogel comprises α

,ω

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

17. A method of making a silicone-containing, hydrogel material comprising:

a) polymerizing a monomer mix comprising;

(1) 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 with m+n+p being from 23 to 200; and

a and b are independently 1 to 10;

(2) 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

(3)at least one hydrophilic monomer; and

(b) hydrating the resulting polymerization product.

18. The method of claim 17 wherein said acrylic-capped polysiloxane prepolymer is comprised of a repeating number of between from about 25 to about 200 dimethylsiloxy units.

19. The method of claim 17 wherein said acrylic-capped polysiloxane prepolymer is an α

,ω

-Bis(methacryloxy alkyl)dialkylsilylpolysiloxane.

20. The method of claim 17 wherein said bulky polysiloxanylalkyl (meth)acrylate monomer is selected form the group consisting of pentamethyldisiloxanylmethyl methacrylate, tris(trimethylsiloxy)methacryloxy propylsilane, phenyltetramethyldisiloxanylethYl acrylate, and methyldi(trimethylsiloxy)methacryloxymethylsilane.

21. The method of claim 17 wherein said bulky polysiloxanylalkyl (meth)acrylate monomer is methacryloxypropyl tris(trimethylsiloxy)silane.

22. The method of claim 17 wherein said 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.

23. The method of claim 17 wherein said hydrophilic monomer is N-vinyl pyrrolidone.

24. The method of claim 17 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.

25. The method of claim 17 wherein said hydrogel comprises both a vinyl-containing hydrophilic monomer and an acrylic-containing hydrophilic monomer.

26. The method of claim 17 wherein said hydrogel comprises at least one crosslinking agent.

27. The method of claim 17 wherein said hydrogel comprises α

,ω

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

28. The method of claim 17 wherein said hydrogel comprises α

,ω

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