Hydrophilic surface modification of contact lenses

• US 20080076851A1
• Filed: 08/28/2007
• Published: 03/27/2008
• Est. Priority Date: 08/28/2006
• Status: Abandoned Application

• Current Assignee: Amin Elachchabi, Daniel Urbaniak, Eugene Goldberg, Khalid Mentak
• Original Assignee: Amin Elachchabi, Daniel Urbaniak, Eugene Goldberg, Khalid Mentak
• Inventors: Goldberg, Eugene, Urbaniak, Daniel, Mentak, Khalid, Elachchabi, Amin
• Application Number:
  US11/892,965
• Publication Number:
  US 20080076851A1
• Time in Patent Office: Days
• US Class Current: 523/106
• CPC Class Codes: C08J 7/18 using wave energy or particle radiation
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

An improved method for modifying the surface of an article, the surface adapted for contact with living tissue of a human or non-human animal, by the gamma- or electron beam-irradiation induced polymerized, chemically grafted coating thereon of a hydrophilic monomer to form a hydrophilic graft polymer coating of the polymerized monomer or mixture of monomers, the improvement comprising conducting the gamma- or electron beam-irradiation induced graft polymerization in an aqueous solution containing a hydrophilic polymer under conditions whereby the hydrophilic polymer is at least partially entrapped in the graft polymerized coating.

Claims

1. In a method for modifying the surface of an article, said surface adapted for contact with living tissue of a human or non-human animal, by the gamma- or electron beam-irradiation induced polymerized, chemically grafted coating thereon of a hydrophilic monomer to form a hydrophilic graft polymer coating of the polymerized monomer or mixture of monomers, the improvement comprising conducting the gamma- or electron beam-irradiation induced graft polymerization in an aqueous solution containing a hydrophilic polymer under conditions whereby said hydrophilic polymer is at least partially entrapped in the graft polymerized coating.

2. The method of claim 1 wherein said hydrophilic polymer is a homo-, co-, terpolymer or polymer comprising a polymer backbone that comprises polar heteroatoms (i.e., wherein the polar heteroatoms present within the polymer backbone of the hydrophilic polymers include, but are not limited to, oxygen, nitrogen, sulfur, or phosphorous), selected from the group consisting of polyalkylene oxides, particularly polyethylene glycol, polyethylene oxide, and poly(ethylene oxide)-poly(propylene oxide) copolymers, including block and random copolymers;

polyols such as glycerol, polyglycerol (particularly highly branched polyglycerol), propylene glycol and trimethylene glycol substituted with one or more polyalkylene oxides, e.g., mono-, di- and tri-polyoxyethylated glycerol, mono- and di-polyoxyethylated propylene glycol, and mono- and di-polyoxyethylated trimethylene glycol;

polyoxyethylated sorbitol, polyoxyethylated glucose;

acrylic acid polymers and analogs and copolymers thereof, such as polyacrylic acid per se, polymethacrylic acid, poly(hydroxyethylmethacrylate), poly(hydroxyethylacrylate), poly(methylalkylsulfoxide methacrylate), poly(methylalkylsulfoxide acrylate) and copolymers of any of the foregoing with additional acrylate species such as aminoethyl acrylate and mono-2-(acryloxy)-ethyl succinate;

polymaleic acid;

poly(acrylamides) such as polyacrylamide per se, poly(methacrylamide), poly(dimethylacrylamide), polydimethylaminoethyl methacrylate, polydimethylaminopropyl methacrylamide, poly(acrylamide/dimethylaminoethyl methacrylate), poly(methacrylic acid/dimethylaminoethyl methacrylate), poly(acrylamide/dimethylaminopropyl methacrylamide), poly(2-acrylamido-2-methyl propane sulfonic acid/dimethylaminoethyl methacrylate), poly (acrylic acid/dimethylaminopropyl methacrylamide), poly(methacrylic acid/dimethylaminopropyl methacrylamide);

poly(N-isopropyl-acrylamide);

poly(olefinic alcohol)s such as poly(vinyl alcohol);

poly(N-vinyl lactams) such as poly(vinyl pyrrolidone), poly(N-vinyl caprolactam), and copolymers thereof;

polyoxazolines, including poly(methyloxazoline) and poly(ethyloxazoline);

polyvinylamines;

polyethylene glycol, polypropylene glycol, branched polyethylene imine, polyvinyl pyrrolidone, polylactide, poly(lactide-co-glycolide), polysorbate, polyethylene oxide, poly(ethylene oxide-co-propylene oxide), poly(oxyethylated) glycerol, poly(oxyethylated) sorbitol, poly(oxyethylated glucose), polymethyloxazoline, polyethyloxazoline, polyhydroxyethyloxazoline, polyhydroxypropyloxazoline, polyvinyl alcohol, poly(hydroxyalkylcarboxylic acid), polyhydroxyethyl acrylic acid, polyhydroxypropyl methacrylic acid, polyhydroxyvalerate, polyhydroxybutyrate, polyoxazolidine, polyaspartamide, polysialic acid, polyalkylene oxide, polyalkyleneimine, polyalkylene amine, polyalkene sulfide, polyalkylene sulfonate, polyalkylene sulfone, poly(alkylenesulfonylalkyleneimine);

celluloses;

polyamides;

polyetheramines;

polyethyleneimines;

polyhydroxyetheramines;

polylysines;

polysulfones;

gums;

starches;

cationic starches (formed by reacting a starch, such as corn, maize, waxy maize, potato, tapioca, and the like, with the reaction product of epichlorohydrin and trialkylamine) and derivatives, mixtures and copolymers thereof.

3. The method of claim 1 wherein said hydrophilic monomer is selected from the group consisting of ethylenically unsaturated C₃-C₆ carboxylic acids, such as acrylic acid, alkyl acrylic acids (particularly methacrylic acid), itaconic acid, maleic acid, fumaric acid, acrylamidomethyl-propanesulfonic acid, vinyl sulfonic acid, vinyl phosphonic acid, vinyllactic acid, and styrene sulfonic acid;

allylamine and allylamine salts formed with an inorganic acid, e.g., hydrochloric acid;

di-C₁-C₃-alkylamino-C₂-C₆-alkyl acrylates and methacrylates such dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, diethylaminoethyl acrylate, diethylaminoethyl methacrylate, dimethylaminopropyl acrylate, dimethylaminobutyl acrylate, dimethylaminoneopentyl acrylate and dimethylaminoneopentyl methacrylate;

olefinically unsaturated nitriles, such as acrylonitrile;

diolefinically unsaturated monomers, particularly diallylammonium compounds such as dimethyldiallylammonium chloride, dimethyldiallylammonium bromide, diethyldiallylammonium chloride, methyl-t-butyldiallylammonium methosulfate, methyl-n-propyldiallylammonium chloride, dimethyldiallylammonium hydrogensulfate, dimethyldiallylammonium dihydrogenphosphate, di-n-butyldiallylammonium bromide, diallylpiperidinium bromide, diallylpyrrolidinium chloride and diallylmorpholinium bromide;

N-vinylpyrrolidone;

N-vinylformamide;

acrylamide and substituted acrylamides, such as N-methylolacrylamide and C₁-C₃ alkyl acrylamides, particularly methacrylamide;

N-vinylimidazole and N-vinylimidazoline; and

other monomers, typically ethylenically unsaturated monomers, preferably vinyl monomers, substituted with at least one hydrophilic functionality such as a carboxylate, a thiocarboxylate, an amide, an imide, a hydrazine, a sulfonate, a sulfoxide, a sulfone, a sulfite, a phosphate, a phosphonate, a phosphonium, an alcohol, a thiol, a nitrate, an amine, an ammonium, or an alkyl ammonium group —

[NHR¹R²]⁺, wherein R¹ and R² are alkyl substituents and the group is associated with a negatively charged anion, e.g., a halogen ion, nitrate, etc;

carboxymethyl cellulose (CMC), hyaluronic Acid (HA) and mixtures thereof.

4. The method of claim 1 wherein said hydrophilic monomer is part of a mixture thereof with up to about 50 wt. %, based on the total monomer weight, of an ionic monomer, salt of an ionic monomer or a mixture thereof.

5. The article produced by the method of claim 1.

6. The article of claim 4 comprising a contact lens.

7. The contact lens of claim 5 comprising a silicone copolymers, a hydrogel, a RGP, a Disposable Hydrogel Contact Lens or an Extended Wear Contact Lens.

8. An article of manufacture comprising packaging material and an article having a surface adapted for contact with living tissue of a human or non-human animal contained within said packaging material, wherein said surface of said article has been modified to enhance contact with said living tissue, and wherein said packaging material comprises a label which indicates that said article is especially adapted for said contact.

9. The article of manufacture of claim 8 wherein said article having a surface adapted for contact with living tissue of a human or non-human animal is a contact lens.