Siloxane hard-coating resin composition

Abstract

The present application relates to a hard-coating resin composition including a siloxane resin, a preparing method of a siloxane cured hard-coating article using same and an optical film including the siloxane cured hard-coating article.

We claim: 
     
         1 . A hard-coating resin composition comprising a siloxane resin including an alicyclic epoxy group,
 wherein the siloxane resin has a weight-average molecular weight in the range of from 1,000 to 4,000 and a molecular weight distribution of PDI ranging from 1.05 to 1.4.   
     
     
         2 . The hard-coating resin composition of  claim 1 , wherein an epoxy equivalent of the siloxane resin is in the range of from 0.35 to 0.6 mol/100 g. 
     
     
         3 . The hard-coating resin composition of  claim 1 , wherein the siloxane resin is prepared by hydrolysis and condensation of (i) an alkoxysilane alone represented by the following Chemical Formula 1 including an alicyclic epoxy group and an alkoxy group, or (ii) an alkoxysilane represented by the following Chemical Formula 1 including an alicyclic epoxy group and an alkoxy group, and an alkoxysilane compound represented by the following Chemical Formula 2, in the presence of water and a catalyst:
   R 1   n Si(OR 2 ) 4-n [  Chemical Formula 1]
     R 3   m Si(OR 4 ) 4-m [  Chemical Formula 2]
   wherein in the formulas,   R 1  is a straight or branched C 1  to C 6  alkyl group including an alicyclic epoxy group,   the alicyclic epoxy group is a C 3  to C 6  cycloalkyl group having an epoxy group,   R 2  is a straight or branched C 1  to C 7  alkyl group,   R 3  is selected from the group consisting of a C 1  to C 20  alkyl group, a C 3  to C 8  cycloalkyl group, a C 2  to C 20  alkenyl group, a C 2  to C 20  alkynyl group, a C 6  to C 20  aryl group, an acryl group, a methacryl group, a halogen group, an amino group, a mercapto group, an ether group, an ester group, a carbonyl group, a carboxyl group, a vinyl group, a nitro group, a sulfone group, and an alkyd group,   R 4  is a straight or branched C 1  to C 7  alkyl group,   n is an integer of from 1 to 3, and   m is an integer of from 0 to 3.   
     
     
         4 . The hard-coating resin composition of  claim 3 , wherein the alkoxysilane represented by Chemical Formula 1 includes 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, or 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane. 
     
     
         5 . The hard-coating resin composition of  claim 3 , wherein the alkoxysilane represented by Chemical Formula 2 includes one or more selected from the group consisting of tetramethoxysilane, tetraethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, triphenylmethoxysilane, triphenylethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltripropoxysilane, N-(3-acryloxy-2-hydroxypropyl)-3-aminopropyltrimethoxysilane, N-(3-acryloxy-2-hydroxypropyl)-3-aminopropyltriethoxysilane, N-(3-acryloxy-2-hydroxypropyl)-3-aminopropyltripropoxysilane, 3-acryloxypropyltriethoxysilane, 3-acryloxypropyltripropoxysilane, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, 3-(meth)acryloxypropyltripropoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, chloropropyltrimethoxysilane, chloropropyltriethoxysilane, and heptadecafluorodecyltrimethoxysilane. 
     
     
         6 . The hard-coating resin composition of  claim 1 , further comprising an acid anhydride monomer containing at least one acid anhydride group capable of reacting with the alicyclic epoxy group of the siloxane resin to thereby form crosslinking. 
     
     
         7 . The hard-coating resin composition of  claim 6 , wherein the acid anhydride monomer includes one or more selected from the group consisting of phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, nadic methyl anhydride, chlorendic anhydride, and pyromellitic dianhydride. 
     
     
         8 . The hard-coating resin composition of  claim 1 , further comprising a monomer having an oxetane group in an amount of from 1 to 40 parts by weight with respect to the siloxane resin of 100 parts by weight. 
     
     
         9 . The hard-coating resin composition of  claim 8 , wherein the monomer having the oxetane group includes one or more selected from the group consisting of 3-methyloxetane, 2-methyloxetane, 3-oxetanol, 2-methyleneoxetane, 3,3-oxetanedimethanethiol, 4-(3-methyloxetane-3-yl)benzonitrile, N-(2,2-dimethylpropyl)-3-methyl-3-oxetanemethanamine, N-(1,2-dimethylbutyl)-3-methyl-3-oxetanemethanamine, (3-ethyloxetane-3-yl)methyl methacrylate, 4-[(3-ethyloxetane-3-yl)methoxy]butan-1-ol, 3-ethyl-3-hydroxymethyloxetane, 2-ethylhexyloxetane, xylylene bisoxetane, and 3-ethyl-3[{(3-ethyloxetane-3-yl)methoxy}methyl]oxetane. 
     
     
         10 . The hard-coating resin composition of  claim 3 , wherein the catalyst is one selected from the group consisting of an acidic catalyst, a basic catalyst, an ion exchange resin and combinations thereof. 
     
     
         11 . The hard-coating resin composition of  claim 3 , wherein the catalyst is one selected from the group consisting of hydrochloric acid, acetic acid, hydrogen fluoride, nitric acid, sulfuric acid, chlorosulfonic acid, iodic acid, pyrophosphoric acid, ammonia, potassium hydroxide, sodium hydroxide, barium hydroxide or imidazole; an ion exchange resin; and combinations thereof. 
     
     
         12 . The hard-coating resin composition of  claim 1 , further comprising a polymerization initiator selected from the group consisting of an onium salt, an organometallic salt, an amine, and an imidazole in an amount of from 0.1 to 10 parts by weight with respect to the siloxane resin of 100 parts by weight. 
     
     
         13 . The hard-coating resin composition of  claim 1 , further comprising one or more additives selected from the group consisting of an organic solvent, an antioxidant, a leveling agent, and a flow control agent. 
     
     
         14 . A preparing method of a cured hard-coating article, comprising a polymerization of the hard-coating resin composition of  claim 1 . 
     
     
         15 . The preparing method of a cured hard-coating article of  claim 14 , wherein the polymerization includes irradiating light or heating. 
     
     
         16 . An optical film or sheet comprising a cured hard-coating article which is prepared by the preparing method as  claim 14 .