Silicone prepolymer solutions

• US 7,897,654 B2
• Filed: 04/01/2008
• Issued: 03/01/2011
• Est. Priority Date: 12/27/2007
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson), Toray Industries Incorporated
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson), Toray Industries Incorporated
• Inventors: Yokota, Mitsuru, Nakamura, Masataka, Fujisawa, Kazuhiko
• Primary Examiner(s): Zimmer; Marc S
• Application Number:
  US12/060,536
• Publication Number:
  US 20090171026A1
• Time in Patent Office: 1,064 Days
• Field of Search: None
• US Class Current: 523/107
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08K 5/06 Ethers; Acetals; Ketals; Ortho-esters
• CPC Class Codes: C08L 39/06 Homopolymers or copolymers of N-vinyl-pyrrolidones
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

In one aspect, the invention relates to silicone prepolymer compositions comprising a silicone prepolymer and a solvent. A soluble silicone prepolymer can be provided having increased average silicon content, thereby attaining a desired oxygen permeability. A solvent can be provided with a desired balance between hydrophilicity and hydrophobicity by selection and modification of the solvent molecular structure, resulting in molded polymer films and articles that exhibit minimal or nonexistent eye irritation and exhibit highly transparent products. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Claims

1. A composition comprising:

a) from about 20% to about 95% content by weight of the composition of a silicone prepolymer having an average silicon content of from about 10% to about 30% by weight of the prepolymer, and

b) from about 5% to about 80% content by weight of the composition of a solvent having a structure represented by formula (1s);

R¹¹—

O-G-R¹³, 

 

(1s)

wherein R¹¹ and R¹³ independently represent hydrogen or an organic radical comprising from 1 to 20 carbon atoms; and

wherein G comprises;

(1) at least one group having a structure represented by formula (1s1);

2. The composition of claim 1, further comprising an initiator.

3. The composition of claim 1, wherein R¹¹ and R¹³ independently represent hydrogen, a C₁-C₂₀ alkyl residue, or a C₁-C₂₀ aryl residue.

4. The composition of claim 1, wherein R¹² represents a C₃-C₂₀ alkylene residue or a C₃-C₂₀ arylene residue.

5. The composition of claim 1, wherein (the number of oxygen atom)/(the number of carbon atom) in the formula (1s) is not more than 0.37.

6. The composition of claim 1, wherein R¹² has a structure represented by formula (1s2-1):

7. The composition of claim 1, wherein the number average molecular weight of the solvent is not more than 450.

8. The composition of claim 1, wherein one of R¹¹ and R¹³ represents hydrogen and the other of R¹¹ and R¹³ represents a C₁-C₁₀ alkyl residue or a C₁-C₁₀ aryl residue.

9. The composition of claim 1, wherein m/(m+n) is from about 0.2 to about 0.8.

10. The composition of claim 1, wherein ethylene oxide residue(s) and —

R¹²—

O—

group(s) in the solvent represented by the formula (s) are randomly copolymerized.

11. The composition of claim 1, wherein the silicone prepolymer comprises:

a) at least one silicone-containing residue having a structure represented by the formula (a);

12. The composition of claim 11, wherein the silicone prepolymer further comprises at least one hydrophilic residue having a structure represented by the following formula (b):

13. A method for producing a polymer comprising the step of polymerizing prepolymer from the composition of claim 1, thereby providing the polymer.

14. The polymer produced by the process of claim 13.

15. An ophthalmic lens comprising the polymer of claim 14.

16. A contact lens comprising the polymer of claim 14.

17. A composition comprising:

a) from about 20% to about 95% content by weight of the composition of a silicone prepolymer having an average silicon content of from about 10% to about 30% by weight of the prepolymer, and

b) from about 5% to about 80% content by weight of the composition of a solvent having a structure represented by formula (2s);

18. The composition of claim 17, further comprising an initiator.

19. The composition of claim 17, wherein R²¹ to R²⁴ independently represent hydrogen, a C₁-C₂₀ alkyl residue, or a C₁-C₂₀ aryl residue or wherein two or more of R²¹ to R²⁴ together form a ring structure.

20. The composition of claim 17, wherein R²⁵ and R²⁶ independently represent hydrogen or a C₁-C₂₀ alkyl residue or a C₁-C₂₀ aryl residue.

21. The composition of claim 17, wherein all of R²¹ to R²⁴ represent hydrogen.

22. The composition of claim 17, wherein one of R²⁵ and R²⁶ represents hydrogen, and the other of R²⁵ and R²⁶ represents a C₃ or higher alkyl residue or C₃ or higher aromatic residue.

23. The composition of claim 17, wherein (n+1)/(2n+r) is not more than 0.40.

24. The composition of claim 17, wherein the number average molecular weight of the solvent is not more than 450.

25. The composition of claim 17, wherein the silicone prepolymer comprises:

a) at least one silicone-containing residue having a structure represented by the formula (a);

26. The composition of claim 25, wherein the silicone prepolymer further comprises at least one hydrophilic residue having a structure represented by the following formula (b):

27. A method for producing a polymer comprising the step of polymerizing prepolymer from the composition of claim 17, thereby providing the polymer.

28. The polymer produced by the process of claim 27.

29. An ophthalmic lens comprising the polymer of claim 28.

30. A contact lens comprising the polymer of claim 28.