Interpenetrating polymer network hydrophilic hydrogels for contact lens

• US 20050148682A1
• Filed: 08/02/2004
• Published: 07/07/2005
• Est. Priority Date: 07/08/1998
• Status: Active Grant

• 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
• Granted Patent: US 7,279,507 B2
• Time in Patent Office: Days
• US Class Current: 523/106
• 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

1-16. -16. (canceled)

17. A contact lens comprising:

a lens body comprising a hydrogel composition comprising

(i) a first hydrophilic polymer component; and

(ii) a different, second hydrophilic polymer component interpenetrating the first polymer component, the second polymer component being water soluble, the lens body having an increased water retention relative to an identical lens body without the second polymer component.

18. The contact lens of claim 17, wherein the first hydrophilic polymer component includes units from a silicon-containing monomer.

19. The contact lens of claim 17, 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.

20. The contact lens of claim 17, wherein the first polymeric component comprises a methacrylate polymer and the second polymeric component comprises a pyrollidone polymer.

21. The contact lens of claim 20, wherein the first polymeric component comprises 2-hydroxyethyl methacrylate and the second polymeric component comprises polyvinylpyrrolidone.

22. The contact lens of claim 17, wherein the first polymer component includes units from a monomer provided in an amount from 5% (w/w) to about 95% (w/w).

23. The contact lens of claim 17, wherein the first polymer component includes units from a monomer provided in an amount from 20% (w/w) to about 85% (w/w).

24. The contact lens of claim 17, further comprising a hydrophilic comonomer effective in forming a hydrogel composition having a water content greater than 40%.

25. The contact lens of claim 24, wherein the hydrophilic comonomer is selected from the group consisting of 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, glycerol monomethacrylate, and mixtures thereof.

26. The contact lens of claim 17, wherein the hydrogel composition further comprises a crosslinker selected from the group consisting of 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, polyethyleneglycol di(meth)acrylate, and mixtures thereof.

27. The contact lens of claim 17, wherein the second polymer component comprises a polymer having a molecular weight from about 10,000 to 1,000,000.

28. The contact lens of claim 17, wherein the second polymer component is provided in an amount from about 1% to 14%.

29. The contact lens of claim 17, wherein the second polymer component is provided in an amount greater than 5%.

30. The contact lens of claim 17, wherein the lens body has a water retention of at least about 96%.

31. A contact lens comprising:

a lens body comprising a hydrogel composition comprising;

(i) a first hydrophilic polymer component; and

(ii) a different second hydrophilic polymer component interpenetrating the first polymer component,

wherein the first polymer component is formed from at least one monomer in a composition containing the second polymer component completely soluble in the composition;

the lens body having increased water retention relative to an identical lens body without the second polymer component.

32. The contact lens of claim 31, wherein the first hydrophilic polymer component includes units from a silicon-containing monomer.

33. The contact lens of claim 31, 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.

34. The contact lens of claim 31, wherein the first polymer component includes units from a monomer provided in an amount from 5% (w/w) to about 95% (w/w).

35. The contact lens of claim 31, further comprising a hydrophilic comonomer effective in forming a hydrogel composition having a water content greater than 40%.

36. The contact lens of claim 31, wherein the second polymer component is provided in an amount greater than 5%.