Process for producing contact lenses with durable lubricious coatings thereon

Abstract

The invention is related to a method for producing soft contact lenses comprises a silicone hydrogel lens body and a composite coating thereon. The composite coating comprises: a plasma base coating which is chemically-attached directly onto the surface of the silicone hydrogel contact lens and functions as a fail-proof measure for ensuring the hydrophobic silicone hydrogel lens material to be shielded from any exposure to ocular environments even after at least 30 days of daily uses including daily waring and daily cleaning/disinfecting; and a relatively-durable lubricious hydrogel top coating for ensuring wearing comfort. A method of the invention comprises forming a plasma-reactive hydrophilic polymer hybrid base coating having reactive functional groups on a silicone hydrogel contact lens and heating the silicone hydrogel contact lens with the hybrid base coating in an aqueous solution of a water-soluble and thermally crosslinkable hydrophilic polymeric material to form a stable lubricious hydrogel coating thereon. This method has a minimized adverse impact on the mechanical properties of silicone hydrogel lens body.

1 - 11 . (canceled) 
     
     
         12 . A soft contact lens, comprising: a silicone hydrogel lens body which is essentially made of a silicone hydrogel material; and a composite coating thereon, wherein the composite coating comprises a plasma base coating substantially free of cracks, an anchor layer of poly(alkylacrylic acid) on top of the plasma base coating, and a hydrogel layer which is covalently attached onto the anchor layer, wherein the plasma base coating has a thickness of from about 0.5 nm to about 40 nm, wherein the poly(alkylacrylic acid)polymer is a homopolymer or copolymer of methacrylic acid, ethyl acrylic acid or 2-(meth)acrylamidoglycolic acid, wherein the soft contact lens in a fully-hydrated state has a friction rating of about 2 or lower after 7 cycles of manual rubbing test and an oxygen permeability of at least about 40 barrers. 
     
     
         13 . The soft contact lens of  claim 12 , wherein the silicone hydrogel material comprises: (i) repeating units of at least one polysiloxane vinylic monomer and/or at least one polysiloxane vinylic crosslinker and (ii) at least one hydrophilic monomer selected from the group consisting of at least one hydrophilic N-vinyl amide monomer, at least one hydroxyl-containing acrylic monomer, at least one alkyl (meth)acrylamide, at least one methylene-containing (═CH 2 ) pyrrolidone monomer, at least one vinyl ether monomer, at least one allyl ether monomer, at least one C 1 -C 4  alkoxyethoxy-containing monomer, at least one phosphorylcholine-containing vinylic monomer. 
     
     
         14 . The soft contact lens of  claim 13 , wherein the silicone hydrogel material comprises: (i) repeating units of at least one non-silicone vinylic crosslinker selected from the group consisting of ethyleneglycol di-(meth)acrylate, diethyleneglycol di-(meth)acrylate, triethyleneglycol di-(meth)acrylate, tetraethyleneglycol di-(meth)acrylate, glycerol di-(meth)acrylate, 1,3-propanediol di-(meth)acrylate, 1,3-butanediol di-(meth)acrylate, 1,4-butanediol di-(meth)acrylate, glycerol 1,3-diglycerolate di-(meth)acrylate, ethylenebis[oxy(2-hydroxypropane-1,3-diyl)] di-(meth)acrylate, bis[2-(meth)acryloxyethyl] phosphate, trimethylolpropane di-(meth)acrylate, and 3,4-bis[(meth)acryloyl]tetrahydrofuan, diacrylamide, dimethacrylamide, N,N-di(meth)acryloyl-N-methylamine, N,N-di(meth)acryloyl-N-ethylamine, N,N′-methylene bis(meth)acrylamide, N,N′-ethylene bis(meth)acrylamide, N,N′-dihydroxyethylene bis(meth)acrylamide, N,N′-propylene bis(meth)acrylamide, N,N′-2-hydroxypropylene bis(meth)acrylamide, N,N′-2,3-dihydroxybutylene bis(meth)acrylamide, 1,3-bis(meth)acrylamidepropane-2-yl dihydrogen phosphate, piperazine diacrylamide, tetraethyleneglycol divinyl ether, triethyleneglycol divinyl ether, diethyleneglycol divinyl ether, ethyleneglycol divinyl ether, triallyl isocyanurate, triallyl cyanurate, trimethylopropane trimethacrylate, pentaerythritol tetramethacrylate, bisphenol A dimethacrylate, allylmethacrylate, allylacrylate, N-allyl-methacrylamide, N-allyl-acrylamide, and combinations thereof. 
     
     
         15 . The soft contact lens of  claim 14 , wherein the hydrogel layer is derived from a water-soluble polymeric material comprising reactive functional groups selected from the group consisting of azetidinium groups, carboxyl groups, primary amino groups, secondary amino groups, thiol groups, and combinations thereof. 
     
     
         16 . The soft contact lens of  claim 15 , wherein the water-soluble polymeric material comprises
 (i) from about 20% to about 95% by weight of first polymer chains derived from a polyamidoamine-epichlorohydrin or a poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin,   (ii) from about 5% to about 80% by weight of hydrophilic moieties and/or second polymer chains,
 wherein each of the hydrophilic moieties is derived from at least one first hydrophilicity-enhancing agent having at least one reactive functional group selected from the group consisting of primary amino group, secondary amino group, carboxyl group, thiol group, and combination thereof, wherein the hydrophilic moieties are covalently attached to the first polymer chains through one or more covalent linkages each formed between one azetitdinium group of the polyamidoamine-epichlorohydrin and one primary or secondary amino, carboxyl or thiol group of the first hydrophilicity-enhancing agent, 
 wherein each of the second polymer chains is derived from at least one second hydrophilicity-enhancing agent having at least one reactive functional group selected from the group consisting of primary amino group, secondary amino group, carboxyl group, thiol group, and combination thereof, wherein the second polymer chains are covalently attached to the first polymer chains through one or more covalent linkages each formed between one azetitdinium group of the polyamidoamine-epichlorohydrin and one primary or secondary amino, carboxyl or thiol group of the second hydrophilicity-enhancing agent, and 
   (iii) azetidinium groups which are parts of the first polymer chains or pendant or terminal groups covalently attached to the first polymer chains.   
     
     
         17 . The soft contact lens of  claim 14 , wherein the second hydrophilicity-enhancing agent is: a polyethylene glycol having one sole primary or secondary amino, carboxyl or thiol group; a polyethylene glycol with two terminal primary or secondary amino, carboxyl and/or thiol groups; a multi-arm polyethylene glycol with one or more primary or secondary amino, carboxyl and/or thiol groups; a polyethylene glycol dendrimer with one or more primary or secondary amino, carboxyl and/or thiol groups; or a copolymer which is a polymerization product of a composition comprising (1) about 60% or less by weight of one or more reactive vinylic monomers and (2) one or more non-reactive hydrophilic vinylic monomers, wherein said one or more reactive vinylic monomers are vinylic monomers having a carboxyl group, a primary amino group, or a secondary amino group, wherein said one or more non-reactive vinylic monomers are selected from the group consisting of a phosphorylcholine-containing vinylic monomer, (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N-vinylpyrrolidone (NVP), N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, N,N-dimethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylamide, glycerol (meth)acrylate, N-2-hydroxylethyl (meth)acrylamide, N,N-bis(hydroxyethyl) (meth)acrylamide, N-3-hydroxypropyl (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide, N-2,3-dihydroxypropyl (meth)acrylamide, N-tris(hydroxymethyl)methyl (meth)acrylamide, N-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, C 1 -C 4 -alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of up to 1500 Daltons, allyl alcohol, vinyl alcohol, and combinations thereof. 
     
     
         18 . The soft contact lens of  claim 17 , wherein the soft contact lens in a fully-hydrated state further has: a WBUT of at least about 10 seconds; a water contact angle of about 80 degrees or less; an elastic modulus of about 1.5 MPa or less; a water content of from about 15% to about 70% when fully hydrated; or combinations thereof. 
     
     
         19 . The soft contact lens of  claim 18 , wherein the plasma base coating has a thickness of from about 3 nm to about 25 nm. 
     
     
         20 . The soft contact lens of  claim 19 , wherein the soft contact lens in a fully-hydrated state has a friction rating of about 1.0 or lower after 7 cycles of manual rubbing test.