Contact lenses

• US 7,279,507 B2
• Filed: 08/02/2004
• Issued: 10/09/2007
• Est. Priority Date: 07/08/1998
• Status: Expired due to Term

• Current Assignee: Coopervision International Limited (The Cooper Cos., Inc.)
• Original Assignee: Coopervision International Holding Company LP (The Cooper Cos., Inc.)
• Inventors: Nguyen, Tung, Briggs, Charles R., Hu, Hopin, Tran, Hue, Rossberg, Filene
• Primary Examiner(s): Szekely; Peter
• Application Number:
  US10/937,868
• Publication Number:
  US 20050148682A1
• Time in Patent Office: 1,163 Days
• Field of Search: 523106-108, 351/160.H
• US Class Current: 523/108
• CPC Class Codes: C08F 265/04 on to polymers of esters
• CPC Class Codes: C08F 271/02 on to polymers of monomers containing heterocyclic nitrogen
• CPC Class Codes: C08F 283/00 Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
• CPC Class Codes: C08F 283/12 on to polysiloxanes
• CPC Class Codes: C08F 291/18 on to irradiated or oxidised macromolecules epoxidised C08F291/10
• CPC Class Codes: C08L 51/00 Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds for ABS polymers C08L55/02; Compositions of derivatives of such polymers
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

An interpenetrating polymer network (IPN) composition and a process for the manufacture of hydrogel contact lens using the invention material. The polymeric materials are formed by polymerization of: (1) an unsaturated alkyl(meth)acrylate or its derivatives such as 2-hydroxyethyl methacrylate as the principle monomer; (2) optionally vinyl containing comonomer(s) to enhance the resulting hydrogel water absorbing capability; (3) polymerizable multi-functional crosslinking agent(s); (4) an irradiation initiator and/or thermal initiator; (5) optionally other additives to impart the resulting hydrogel specific properties such as ultra-violet blocking ability and handling colors; in the presence of a soluble, hydrophilic IPN agent such as polyvinylpyrrolidone (PVP) or poly-2-ethyl-2-oxazoline (PEOX) with a specific molecular weight range. The novel hydrophilic hydrogel material in the present invention can be used to produce a spherical contact lens, a toric contact lens, a multifocal contact lens, a toric-multifocal contact lens, and other medical devices. The inventive hydrogel material shows a low degree of surface friction, a low dehydration rate, and a high degree of biodeposit resistance.

Claims

1. A contact lens comprising:

a molded lens body comprising a hydrogel interpenetrating polymer network composition comprising

a first hydrophilic polymer component formed from a polymerization of one or more monomers and a crosslinker that crosslinks said one or more monomers, and said polymerization taking place in the presence of a pre-formed second hydrophilic polymer component; and

said pre-formed second hydrophilic polymer component interpenetrating the first hydrophilic polymer component, the second polymer component being water soluble,

the molded lens body having an increased water retention relative to an identical lens body without the second polymer component, wherein said second hydrophilic polymer component is present in an amount of from 5% to 10% based on the weight of said hydrogel composition.

2. The contact lens of claim 1, wherein the first hydrophilic polymer component includes units from a silicon-containing monomer.

3. The contact lens of claim 1, wherein the second polymer component is selected from the group consisting of

(A) at least one polymer comprising one or more monomeric units comprising at least one ═

N—

C(═

O)—

group;

(B) at least one polymer comprising one or more monomeric units comprising at least one N-oxide group;

(C) at least one polymer comprising both ═

N—

C(═

O)— and

N-oxide groups of(A) and (B); and

(D) mixtures thereof.

4. The contact lens of claim 1, wherein the first polymeric component comprises a methacrylate polymer and the second polymeric component comprises a pyrrolidone polymer.

5. The contact lens of claim 4, wherein the first polymeric component comprises 2-hydroxyethyl methacrylate and the second polymeric component comprises polyvinylpyrrolidone.

6. The contact lens of claim 1, wherein the first polymer component includes units from a monomer provided in an amount from 5% (w/w) to about 95% (w/w).

7. The contact lens of claim 1, wherein the first polymer component includes units from a monomer provided in an amount from 20% (w/w) to about 85% (w/w).

8. The contact lens of claim 1, further comprising a hydrophilic comonomer effective in forming a hydrogel composition having a water content greater than 40%.

9. The contact lens of claim 8, wherein the hydrophilic comonomer is acrylic acid, methacrylic acid, sulfoxide containing (meth)acrylate, N-vinylpyrrolidone, 2-acrylamido-2-methylpropanesulfonic acid and its salts, vinyl sulfonic acid and its salts, styrenesulfonic acid and its salts, 3-methacryloyloxy propyl sulfonic acid and its salts, allylsulfonic acid, 2-methacryloyloxyethyltrimethylammonium salts, N,N,N-trimethylammonium salts, diallyl-dimethylammonium salts, polyethylene glycol (400) monomethyl ether monomethacrylate, or glycerol monomethacrylate, or mixtures thereof.

10. The contact lens of claim 1, wherein the hydrogel composition further comprises a crosslinker selected from ethyleneglycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, tetraethyleneglycol di(meth)acrylate, trimethylopropane tri(meth)acrylate, bisphenol A di(meth)acrylate, ethoxylate bisphenol A di(meth)acrylate, pentaerythritol tri-, and tetra(meth)acrylate, tetramethylene di(meth)acrylate, methylenebisacrylamide, methacryloxyethyl vinyl carbonate, triallylcyanurate, methacryloxyethyl vinyl urea, divinyl benzene, diallyl itaconate, allyl methacrylate, diallyl phthalate, polysiloxanylbisalkyl (meth)acrylate, or polyethyleneglycol di(meth)acrylate, or mixtures thereof.

11. The contact lens of claim 1, wherein the second polymer component comprises a polymer having a weight average molecular weight from about 10,000 to 1,000,000.

12. The contact lens of claim 1, wherein the lens body has a water retention of at least 96%.

13. The contact lens of claim 1, wherein the first hydrophilic polymer component is dimethyl diphenyl methylvinyl siloxane;

X-(dimethylvinylsilyl)-w-[(dimethylvinylsilyl)oxy]-dimethyl diphenyl methylvinyl siloxane;

vinyl [3-[3,3,3-trimethyl- 1,1-bis(trimethylsiloxy-)disiloxany]propyl] carbonate;

or 4,4′

-(tetrapentacontmethyl-hepta-cosasiloxanylene)di-1-butanol), or combinations thereof.

14. The contact lens of claim 1, wherein the second hydrophilic polymer component is polyvinylpyrrolidone.

15. The contact lens of claim 14, wherein the polyvinylpyrrolidone has a weight average molecular weight greater than 10,000.

16. The contact lens of claim 14, wherein the polyvinylpyrrolidone has a weight average molecular weight less than 1,000,000.

17. The contact lens of claim 14, wherein the polyvinylpyrrolidone has a weight average molecular weight from 10,000 to 100,000.

18. The contact lens of claim 14, wherein the polyvinylpyrrolidone has a weight average molecular weight from 30,000 to 80,000.

19. The contact lens of claim 1, wherein the polymerization takes place in the presence of an ultraviolet absorbing agent, polymerization initiator, colorant, or antiseptic agent, or any combination thereof.

20. The contact lens of claim 1, wherein said crosslinker is polyethylene glycol dimethacrylate, or ethylene glycol dimethacrylate, or any combination thereof.

21. The contact lens of claim 1, wherein the crosslinker is present in an amount from approximately 0.1 wt % to approximately 8 wt %.

22. The contact lens of claim 1, wherein said contact lens is a spherical contact lens, aspherical contact lens, or toric contact lens.

23. The contact lens of claim 1, wherein said crosslinker is ethyleneglycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, tetraethyleneglycol di(meth)acrylate, trimethylopropane tri(meth)acrylate, bisphenol A di(meth)acrylate, ethoxylate bisphenol A di(meth)acrylate, pentaerythritol tri-, and tetra(meth)acrylate, tetramethylene di(meth)acrylate, methylenebisacrylamide, methacryloxyethyl vinyl carbonate, triallylcyanurate, methacryloxyethyl vinyl urea, divinyl benzene, diallyl itaconate, allyl methacrylate, diallyl phthalate, polysiloxanylbisalkyl (meth)acrylate, or polyethyleneglycol di(meth)acrylate, or mixtures thereof.

53. The contact lens of claim 1, wherein said molded lens body has:

a water loss of less than approximately 5 weight percent after 5 minutes at approximately 75% humidity and approximately 24°

C.

24. A molded contact lens comprising a polymerized reaction product of at least one polymerizable monomer and a crosslinker, wherein said polymerized reaction product is formed in the presence of a polyvinylpyrrolidone having a weight average molecular weight of at least 10,000, the polyvinylpyrrolidone being present in the composition in an amount from approximately 1% to 14%.

25. The molded contact lens of claim 24, wherein the polyvinylpyrrolidone has a weight average molecular weight less than 1,000,000.

26. The molded contact lens of claim 24, wherein the polyvinylpyrrolidone has a weight average molecular weight from 10,000 to 100,000.

27. The molded contact lens of claim 26, wherein the polyvinylpyrrolidone has a weight average molecular weight from 30,000 to 80,000.

28. The molded contact lens of claim 24, wherein the polyvinylpyrrolidone is present in an amount from 5 wt % to approximately 10 wt %.

29. The molded contact lens of claim 24, wherein said reaction product includes in the reaction an ultraviolet absorbing agent, a polymerization initiator, a colorant, or an antiseptic agent, or combinations thereof.

30. The molded contact lens of claim 24, wherein the reaction product is a radiated product that has been exposed to radiation.

31. The molded contact lens of claim 30, wherein the radiation is selected from the group consisting of E-beam radiation, ultraviolet radiation, thermal radiation, microwave radiation, and combinations thereof.

32. The molded contact lens of claim 30, wherein the reaction product is a thermal polymerized product, photochemical polymerized product, or a combination thereof.

33. The molded contact lens of claim 24, wherein said contact lens has a water retention of at least 96%.

34. The molded contact lens of claim 24, wherein said contact lens has a water content greater than 40% to about 60%.

35. The molded contact lens of claim 24 which is a contact lens selected from the group consisting of spherical contact lenses, aspherical contact lenses, and toric contact lenses.

36. The molded contact lens of claim 24 which has a reduced surface friction relative to a contact lens comprising the reaction product of an identical polymerizable composition without the polyvinylpyrollidone.

57. The molded contact lens of claim 24, wherein said molded contact lens has a water loss of less than approximately 5 weight percent after 5 minutes at approximately 75% humidity and approximately 24°

C.

37. A contact lens comprising:

a molded lens body comprising a hydrogel interpenetrating polymer network composition comprising

a first polymer component formed from a polymerization of one or more monomers and a crosslinker that crosslinks said one or more monomers, and said polymerization taking place in the presence of a second hydrophilic polymer component; and

said second hydrophilic polymer component interpenetrating the first polymer component, the second hydrophilic polymer component being selected from the group consisting of polyvinylpyrrolidone, poly-2-ethyl-2-oxazoline, poly(4- vinylpyridine N-oxide) and combinations thereof,

wherein approximately 1 wt % to 14 wt % of the second hydrophilic polymer component is present.

38. The contact lens of claim 37, wherein the first polymeric component comprises a methacrylate polymer and the second polymeric component comprises a polyvinylpyrrolidone.

39. The contact lens of claim 38, wherein the first polymeric component comprises 2-hydroxyethyl methacrylate and the second polymeric component comprises polyvinylpyrrolidone.

40. The contact lens of claim 37, wherein the first polymer component includes units from a monomer provided in an amount from 5% (w/w) to about 95% (w/w).

41. The contact lens of claim 37, wherein the first polymer component includes units from a monomer provided in an amount from 20% (w/w) to about 85% (w/w).

42. The contact lens of claim 37, further comprising a hydrophilic comonomer effective in forming a hydrogel composition having a water content greater than 40% to about 60%.

43. The contact lens of claim 42, wherein the hydrophilic comonomer is acrylic acid, methacrylic acid, sulfoxide containing (meth)acrylate, N-vinylpyrrolidone, 2-acrylamido-2-methylpropanesulfonic acid and its salts, vinyl sulfonic acid and its salts, styrenesulfonic acid and its salts, 3-methacryloyloxy propyl sulfonic acid and its salts, allylsulfonic acid, 2-methacryloyloxyethyltrimethylammonium salts, N,N,N-trimethylammonium salts, diallyl-dimethylammonium salts, polyethylene glycol (400) monomethyl ether monomethacrylate, or glycerol monomethacrylate, or mixtures thereof.

44. The contact lens of claim 37, wherein the crosslinker is ethyleneglycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, tetraethyleneglycol di(meth)acrylate, trimethylopropane tri(meth)acrylate, bisphenol A di(meth)acrylate, ethoxylate bisphenol A di(meth)acrylate, pentaerythritol tri-, and tetra(meth)acrylate, tetramethylene di(meth)acrylate, methylenebisacrylamide, methacryloxyethyl vinyl carbonate, triallylcyanurate, methacryloxyethyl vinyl urea, divinyl benzene, diallyl itaconate, allyl methacrylate, diallyl phthalate, polysiloxanylbisalkyl (meth)acrylate, or polyethyleneglycol di(meth)acrylate, or mixtures thereof.

45. The contact lens of claim 37, wherein the second polymer component comprises a polymer having a weight average molecular weight from about 10,000 to 1,000,000.

46. The contact lens of claim 37, wherein the second polymer component is provided in an amount greater than 5% to 10% by weight.

47. The contact lens of claim 37, wherein the second polymer component is polyvinylpyrrolidone provided in an amount greater than 5% to 10% by weight.

48. The contact lens of claim 37, wherein the lens body has a water retention of at least 96%.

49. A hydrogel contact lens comprising:

a molded lens body comprising a hydrogel interpenetrating polymer network composition comprising;

(i) a first polymer component formed from a polymerization of one or more monomers and a crosslinker that crosslinks said one or more monomers, and said polymerization taking place in the presence of a polyvinylpyrrolidone; and

(ii) said polyvinylpyrrolidone interpenetrating the first polymer component,

wherein approximately 1 wt % to 14 wt % of the polyvinylpyrrolidone component is present.

50. The contact lens of claim 49, wherein the first polymer component includes units from a monomer provided in an amount from 5% (w/w) to about 95% (w/w).

51. The contact lens of claim 49, further comprising a hydrophilic comonomer effective in forming a hydrogel composition having a water content greater than 40% to about 60%.

52. The contact lens of claim 49, wherein the polyvinylpyrrolidone component is provided in an amount greater than 5% to 10% by weight.

54. A contact lens, comprising:

a molded lens body obtained from a contact lens mold assembly including a female lens mold and a male lens mold, the molded lens body comprising a polymerized reaction product of at least one polymerizable monomer and a crosslinker, and taking place in the presence of a preformed polyvinylpyrrolidone polymer having a weight average molecular weight of at least 10,000; and

wherein the polyvinylpyrrolidone polymer is present in the composition in an amount from approximately 1 wt % to 14 wt %.

55. A contact lens, comprising:

a molded lens body obtained from a contact lens mold assembly including a female lens mold and a male lens mold, the molded lens body comprising a polymerized reaction product of at least one polymerizable monomer and a crosslinker, wherein said reaction product is formed in the presence of a preformed polyvinylpyrrolidone polymer having a weight average molecular weight of at least 10,000; and

wherein the polyvinylpyrrolidone polymer is present in the composition in an amount from approximately 1 wt % to 14 wt %.

56. A contact lens, comprising:

a molded lens body obtained from a contact lens mold assembly including a female lens mold and a male lens mold, the molded lens body comprising a polymerized reaction product of at least one polymerizable monomer and a crosslinker and taking place in the presence of a preformed polyvinylpyrrolidone polymer, wherein said polyvinylpyrrolidone polymer interpenetrates said polymerized reaction product and said preformed polyvinylpyrrolidone polymer having a weight average molecular weight of at least 10,000; and

wherein the polyvinylpyrrolidone polymer is present in the composition in an amount from approximately 1 wt % to 14 wt %.