Amphiphilic networks, process for producing same, and products made therefrom

• US 7,642,332 B2
• Filed: 08/14/2007
• Issued: 01/05/2010
• Est. Priority Date: 08/14/2006
• Status: Active Grant

• Current Assignee: University of Akron
• Original Assignee: University of Akron
• Inventors: Karunakaran, Radhakrishnan, Kennedy, Joseph P.
• Primary Examiner(s): Gulakowski; Randy
• Assistant Examiner(s): LOEWE, ROBERT S
• Application Number:
  US11/891,899
• Publication Number:
  US 20080045661A1
• Time in Patent Office: 875 Days
• Field of Search: 528/25, 528/31
• US Class Current: 528/31
• CPC Class Codes: C08F 283/00 Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
• CPC Class Codes: C08F 283/06 on to polyethers, polyoxymethylenes or polyacetals C08F283/004 takes precedence
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G

Abstract

The present invention relates to the production of amphiphilic copolymer networks, or co-networks, and to methods for preparing amphiphilic co-networks. Furthermore, the present invention relates to products and/or films made from the amphiphilic co-networks produced in accordance with the synthesis methods of the present invention. Additionally, the present invention relates to crosslinked amphiphilic co-networks comprising at least one hydrophilic segment and at least one hydrophobic segment. In one embodiment, the hydrophilic segments include at least one polyalkyl glycol (e.g., polyethylene glycol (PEG)) and the hydrophobic segments include at least one di-alkenyl and/or di-alkynyl terminated polysiloxane (e.g., polydimethylsiloxane (PDMS)). In another embodiment, the amphiphilic co-networks of the present invention are optically clear and highly oxophilic.

Claims

1. A multicomponent network comprising the reaction product of at least one hydrophilic polymer, at least one hydrophobic polymer and at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition according to the following formula:

2. The multicomponent network of claim 1, wherein the at least one hydrophilic polymer is selected from one or more polyalkyl glycol polymers, one or more di-alkenyl or di-alkynyl terminated poly N-vinyl pyrrolidinone polymers, one or more di-alkenyl or di-alkynyl terminated poly-dimethylacrylamide polymers, one or more di-alkenyl or di-alkynyl terminated poly-oxazoline polymers, or combinations of two or more different hydrophilic polymers thereof.

3. The multicomponent network of claim 2, wherein the number of repeating units in the one or more hydrophilic polymers is in the range of about 5 to about 5,000.

4. The multicomponent network of claim 2, wherein the number of repeating units in the one or more hydrophilic polymers is in the range of about 40 to about 500.

5. The multicomponent network of claim 1, wherein the at least one hydrophobic polymer is selected from at least one di-alkenyl or di-alkynyl terminated siloxane polymer.

6. The multicomponent network of claim 5, wherein the number of repeating siloxane repeating units in the at least one di-alkenyl or di-alkynyl terminated siloxane polymer is in the range of about 5 to about 5,000.

7. The multicomponent network of claim 5, wherein the number of repeating siloxane repeating units in the at least one di-alkenyl or di-alkynyl terminated siloxane polymer is in the range of about 40 to about 500.

8. The multicomponent network of claim 1, wherein the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition is selected from one or more of D₅H.TRIS, D₅H.OFPE, and/or D₅H.DEG.

9. The multicomponent network of claim 1, wherein the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition is D₅H.TRIS having a chemical formula as shown below:

10. The multicomponent network of claim 1, wherein the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition is D₅H.OFPE having a chemical formula as shown below:

11. The multicomponent network of claim 1, wherein the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition is D₅H.DEG having a chemical formula as shown below:

12. The multicomponent network of claim 1, wherein the multicomponent network is used to produce a film.

13. The multicomponent network of claim 1, wherein the multicomponent network is used to produce a contact lens.

14. A multicomponent network comprising the reaction product of at least one hydrophilic polymer, at least one polydimethylsiloxane polymer and at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition according to the following formula:

15. The multicomponent network of claim 14, wherein the at least one hydrophilic polymer is selected from one or more polyalkyl glycol polymer, one or more di-alkenyl or di-alkynyl terminated poly N-vinyl pyrrolidinone polymers, one or more di-alkenyl or di-alkynyl terminated poly-dimethylacrylamide polymers, one or more di-alkenyl or di-alkynyl terminated poly-oxazoline polymers, or combinations of two or more different hydrophilic polymers thereof.

16. The multicomponent network of claim 15, wherein the number of repeating units in the one or more hydrophilic polymers is in the range of about 40 to about 500.

17. The multicomponent network of claim 14, wherein the at least one hydrophilic polymer is selected from one or more polyalkyl glycol polymers.

18. The multicomponent network of claim 14, wherein the number of repeating siloxane repeating units in the at least one polydimethylsiloxane polymer is in the range of about 40 to about 500.

19. The multicomponent network of claim 14, wherein the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition is selected from one or more of D₅H.TRIS, D₅H.OFPE, and/or D₅H.DEG.

20. The multicomponent network of claim 14, wherein the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition is D₅H.TRIS having a chemical formula as shown below:

21. The multicomponent network of claim 14, wherein the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition is D₅H.OFPE having a chemical formula as shown below:

22. The multicomponent network of claim 14, wherein the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition is D₅H.DEG having a chemical formula as shown below:

23. The multicomponent network of claim 14, wherein the multicomponent network is an amphiphilic co-network.

24. The multicomponent network of claim 14, wherein the multicomponent network is used to produce a film.

25. The multicomponent network of claim 14, wherein the multicomponent network is used to produce a contact lens.

26. A multicomponent network comprising the reaction product of at least one hydrophilic polymer, at least one di-alkenyl or di-alkynyl terminated polysiloxane polymer and at least one mono-, di-, tri- or tetra-modified cyclopentasiloxane crosslinking composition as shown in the formula below:

27. The multicomponent network of claim 26, wherein the at least one hydrophilic polymer is selected from one or more polyalkyl glycol polymer, one or more di-alkenyl or di-alkynyl terminated poly N-vinyl pyrrolidinone polymers, one or more di-alkenyl or di-alkynyl terminated poly-dimethylacrylamide polymers, one or more di-alkenyl or di-alkynyl terminated poly-oxazoline polymers, or combinations of two or more different hydrophilic polymers thereof.

28. The multicomponent network of claim 27, wherein the at least one hydrophilic polymer is selected from one or more polyalkyl glycol polymers.

29. The multicomponent network of claim 26, wherein the at least one di-alkenyl or di-alkynyl terminated polydimethylsiloxane polymer is selected from any polymer according to the general formula shown below:

30. The multicomponent network of claim 29, wherein R₁ and R₂ are identical substituent groups.

31. The multicomponent network of claim 29, wherein R₃ and R₄ are identical substituent groups.

32. The multicomponent network of claim 26, wherein the crosslinking composition is a di-modified cyclopentasiloxane crosslinking composition.

33. The multicomponent network of claim 26, wherein the crosslinking composition is a tri-modified cyclopentasiloxane crosslinking composition.

34. A crosslinking composition comprising at least one mono-modified alkyl-substituted cyclopentasiloxane according to the following formula:

35. A crosslinking composition comprising at least one mono-modified alkyl-substituted cyclopentasiloxane according to the following formula:

36. A crosslinking composition comprising at least one mono-modified alkyl-substituted cyclopentasiloxane according to the following formula:

37. A crosslinking composition comprising at least one mono-modified alkyl-substituted cyclopentasiloxane according to the following formula:

38. A method for forming an amphiphilic network or co-network comprising the steps of:

(A) combining at least one hydrophilic polymer and at least one hydrophobic polymer to form a polymer mixture;

(B) adding at least one mono-, di-, tri- or tetra-modified cyclopentasiloxane composition to the polymer mixture of Step (A) to form a polymer-crosslinker mixture, the at least one mono-, di-, tri- or tetra-modified cyclopentasiloxane composition having a chemical formula as shown below;

39. The method of claim 38, wherein the at least one hydrophilic polymer is selected from one or more polyalkyl glycol polymer, one or more di-alkenyl or di-alkynyl terminated poly N-vinyl pyrrolidinone polymers, one or more di-alkenyl or di-alkynyl terminated poly-dimethylacrylamide polymers, one or more di-alkenyl or di-alkynyl terminated poly-oxazoline polymers, or combinations of two or more different hydrophilic polymers thereof.

40. The method of claim 38, wherein the at least one hydrophobic polymer is selected from at least one di-alkenyl or di-alkynyl terminated siloxane polymer.

41. A polymer film produced by the method of claim 38.

42. A contact lens produced by the method of claim 38.

43. An amphiphilic co-network produced by the method of claim 38.

44. A method for forming an amphiphilic network or co-network comprising the steps of:

(i) combining at least one hydrophilic polymer and at least one hydrophobic polymer to form a polymer mixture;

(ii) adding at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition to the polymer mixture of Step (i) to form a polymer-crosslinker mixture, the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition having a chemical formula as shown below;

45. The method of claim 44, wherein the at least one hydrophilic polymer is selected from one or more polyalkyl glycol polymer, one or more di-alkenyl or di-alkynyl terminated poly N-vinyl pyrrolidinone polymers, one or more di-alkenyl or di-alkynyl terminated poly-dimethylacrylamide polymers, one or more di-alkenyl or di-alkynyl terminated poly-oxazoline polymers, or combinations of two or more different hydrophilic polymers thereof.

46. The method of claim 44, wherein the at least one hydrophobic polymer is selected from at least one di-alkenyl or di-alkynyl terminated siloxane polymer.

47. The method of claim 44, wherein the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition is selected from one or more of D₅H.TRIS, D₅H.OFPE, and/or D₅H.DEG.

48. The method of claim 44, wherein the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition is D₅H.TRIS having a chemical formula as shown below:

49. The method of claim 44, wherein the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition is D₅H.OFPE having a chemical formula as shown below:

50. The method of claim 44, wherein the at least one mono-modified alkyl-substituted cyclopentasiloxane crosslinking composition is D₅H.DEG having a chemical formula as shown below:

51. An amphiphilic co-network produced by the method of claim 44.

52. A polymer film produced by the method of claim 44.

53. A contact lens produced by the method of claim 44.