Optically transparent hydrogels and processes for their production

• US RE39,635 E1
• Filed: 02/28/2002
• Issued: 05/15/2007
• Est. Priority Date: 09/30/1998
• Status: Expired due to Term

• Current Assignee: Douglas G. Vanderlaan, Frank Molock, Giancarlo Fruzzetti
• Original Assignee: Douglas G. Vanderlaan, Frank Molock, Giancarlo Fruzzetti
• Inventors: Molock, Frank, Vanderlaan, Douglas G., Fruzzetti, Giancarlo
• Primary Examiner(s): Moore; Margaret G.
• Application Number:
  US10/085,261
• Time in Patent Office: 1,902 Days
• Field of Search: 526/279, 522/99, 525/383
• US Class Current: 526/279
• CPC Class Codes: C08F 230/08 containing silicon

Abstract

The invention provides hydrogels for use in the production of biomedical devices. In particular, the invention provides hydrogels formed from siloxane prepolymers and a hydrophilic monomer, which hydrogels are optically transparent.

Claims

1. A process for producing a hydrogel comprising:

a.) polymerizing a hydrophobic siloxane prepoplymer and a silylated hydrophilic monomer; and

b.) hydrolyzing the resulting polymer wherein the step a.) polymerizing is carried out by using one of heat polymerization, ultraviolet light polymerization, radiation polymerization, or a combination thereof.

2. The process of claim 1 wherein the hydrophobic siloxane prepolyer and the silylated hydrophilic monomer are polymerized with a hydrophobic siloxane monomer.

3. The process of claim 2 wherein the hydrophobic siloxane monomer is of the formula:

wherein R¹⁹ and R²⁰ are each independently hydrogen or methyl, R²¹, R²², and R²³ are each independently a monovalent alkyl of 1 to 5 carbon atoms or aryl, j=1 to 10 and k=0 to 3.

4. The process of claim 3, wherein the hydrophobic siloxane monomer is 3-methacryloxypropyltris (trimethylsiloxy)silane or 3-methacryloxypropylbis (trimethylsiloxy)methylsilane.

5. The process of claim 1 or 3 wherein the hydrophobic siloxane prepolymer is of the formula:

wherein R¹ is hydrogen or an alkyl of 1 to 5 carbon atoms, R² is an alkyl of 1 to 5 carbon atoms, n=1 to 12, and z=1 to 500 and the silylated hydrophilic monomer is of the formula;

wherein R²⁴ is hydrogen or methyl, R²⁵ is hydrogen or methyl, and R²⁶ is a monoalkyl.

6. The process of claim 5 wherein the hydrophobic siloxane prepolymer is a α

,ω

-bismethacryloxypropyl macromer and the silylated hydrophilic monomer is a polyalkylsilyl ether of a hydroxyalkyl(meth)acrylamide.

7. The process of claim 6 wherein the hydrophobic siloxane prepolymer is α

,ω

-bismethacryloxypropyl polydimethylsiloxane and the silylated hydrophilic monomer is 2-hydroxymethacrylamide trimethylsilyl ether.

17. The process of claim 1, wherein the polymerizing step a.) is carried out using ultraviolet light.

18. The process of claim 5, wherein the polymerizing step a.) is carried out using ultraviolet light.

19. The process of claim 6, wherein the polymerizing step a.) is carried out using ultraviolet light.

8. A hydrogel comprising a hydrophobic siloxane prepolymer and a silylated hydrophilic monomer.

9. The hydrogel of claim 8 further comprising a hydrophobic siloxane monomer.

10. The hydrogel of claim 9 wherein the hydrophobic siloxane monomer is of the formula:

wherein R¹⁹ and R²⁰ are each independently hydrogen or methyl, R²¹, R²², and R²³ are each independently a monovalent alkyl of 1 to 5 carbon atoms or aryl, j=1 to 10 and k=0 to 3.

11. The hydrogel of claim 10, wherein the hydrophobic siloxane monomer is 3-methacryloxypropyltris (methylsiloxy)silane or 3-methacryloxypropylbis (trimethylsiloxy)methylsilane.

12. The hydrogel of claim 8 or 10 wherein the hydrophobic siloxane prepolymer is of the formula:

wherein R¹ is hydrogen or an alkyl of 1 to 5 carbon atoms, R² is an alkyl of 1 to 5 carbon atoms, n=1 to 12, and z=1 to 500 and the silylated hydrophilic monomer is of the formula;

wherein R²⁴ is hydrogen or methyl, R²⁵ is hydrogen or methyl, and R²⁶ is a monoalkyl.

13. The hydrogel of claim 12 wherein the hydrophobic siloxane prepolymer is a α

,ω

-bismethacryloxypropyl macromer and the silylated hydrophilic monomer is a polyalkylsilyl ether of a hydroxyalkyl(meth)acrylamide.

14. The hydrogel of claim 13 wherein the hydrophobic siloxane prepolymer is α

,ω

-bismethacryloxypropyl polydimethylsiloxane and the silylated hydrophilic monomer is 2-hydroxymethacrylamide trimethylsilyl ether.

15. The hydrogel of claim 8 wherein the hydrophobic siloxane prepolymer is present in an amount of about 5 to about 70 weight percent and the amount of silylated hydrophilic monomer is present in an amount of about 2 to about 60 weight percent.

16. The hydrogel of claim 9 wherein the amount of siloxane prepolymer used is about 5 to about 70 weight percent, the amount of siloxane monomer used is from about 0 to about 70 weight percent, and the amount of silylated monomer used is from about 2 to about 60 weight percent.

20. The hydrogel of claim 13 wherein the amount of siloxane prepolymer used is about 5 to about 70 weight percent, the amount of siloxane monomer used is from about 0 to about 70 weight percent, and the amount of silylated monomer used is from about 2 to about 60 weight percent.

21. The hydrogel of claim 14 wherein the amount of siloxane prepolymer used is about 5 to about 70 weight percent, the amount of siloxane monomer used is from about 0 to about 70 percent, and the amount of silylated monomer used is from about 2 to about 60 weight percent.