Curable resin composition, cured product thereof, and various articles derived from those

Abstract

A curable resin composition which is easily cured by heating or ultraviolet irradiation and capable of forming a thick cured film due to low shrinkage. This curable resin composition enables to obtain a cured product satisfying various characteristics such as heat resistance, chemical resistance, high surface hardness and high refractive index. Also disclosed is a cured product obtained from such a composition. Specifically disclosed is a curable resin composition containing at least one substance selected from the group consisting of condensates (A) obtained by hydrolyzing and condensing a thiol group-containing alkoxysilane (a1) represented by the following general formula (1): R1Si(OR2)3 (1) (wherein, R1 represents a hydrocarbon group having at least one thiol group and 1-8 carbon atoms or an aromatic hydrocarbon group having at least one thiol group, and R2 represents a hydrogen atom, a hydrocarbon group having 1-8 carbon atoms or an aromatic hydrocarbon group), compounds (B) having an epoxy group, compounds (C) having an isocyanate group and compounds (D) having a carbon-carbon double bond.

1 . A curable resin composition comprising:
 a condensate (A) obtained by hydrolysis and condensation of a thiol-containing alkoxysilanes (a1) of the general formula (1):
   R 1 Si(OR 2 ) 3   (1) 
 (wherein R 1  represents a hydrocarbon group of carbon number 1 to 8 having at least one thiol group, or an aromatic hydrocarbon group having at least one thiol group; and R 2  represents a hydrogen atom, hydrocarbon group of carbon number 1 to 8 or aromatic hydrocarbon group); and 
   at least one kind selected from a group of a compound having an epoxy group (B), a compound having an isocyanate group (C) and a compound having a carbon-carbon double bond (D).   
     
     
         2 . The curable resin composition of  claim 1 , wherein the condensate (A) is prepared by hydrolysis of alkoxysilanes (a1) in the presence of formic acid, followed by condensation reaction of the hydrolysate in the presence of a solvent. 
     
     
         3 . The curable resin composition of  claim 1 , wherein the condensate (A) further comprises metal alkoxides (a2) having no thiol group as the constituent. 
     
     
         4 . The curable resin composition which is prepared by hydrolysis of the thiol-containing alkoxysilanes (a1) of the general formula (1):
   R 1 Si(OR 2 ) 3   (1)   (wherein R 1  represents a hydrocarbon group of carbon number 1 to 8 having at least one thiol group, or an aromatic hydrocarbon group having at least one thiol group; and R 2  represents a hydrogen atom, hydrocarbon group of carbon number 1 to 8 or aromatic hydrocarbon group) in the presence of formic acid, followed by condensation reaction of the hydrolysate in the presence of a solvent and a compound (D) having a carbon-carbon double bond.   
     
     
         5 . The curable resin composition of  claim 1 , wherein the alkoxysilanes (a1) is 3-mercaptopropyltrimethoxysilane. 
     
     
         6 . The curable resin composition of  claim 1 , wherein the compound (B) is at least one kind of compound selected from a group of a bisphenol A-type epoxy resin, bisphenol F-type epoxy resin, hydrogenated bisphenol A-type epoxy resin and alicyclic epoxy resin. 
     
     
         7 . The curable resin composition of  claim 1 , wherein the compound (B) has at least two epoxy groups in a molecule. 
     
     
         8 . The curable resin composition of  claim 1 , wherein the compound (C) is isophorone diisocyanate. 
     
     
         9 . The curable resin composition of  claim 1 , wherein the compound (D) is an allyl group-containing compound. 
     
     
         10 . The curable resin composition of  claim 1 , further comprising alkoxysilanes (a1) and/or the hydrolysate (excluding condensate thereof) (E). 
     
     
         11 . The curable resin composition of  claim 10 , wherein the component (E) is 3-mercaptopropyltrimethoxysilane and/or the hydrolysate (excluding condensate thereof). 
     
     
         12 . The curable resin composition of  claim 1 , further comprising metal alkoxides (a2) and/or the hydrolysate (excluding condensate thereof) (F). 
     
     
         13 . The curable resin composition of  claim 12 , wherein the component (F) is at least one kind selected from a group of alkoxysilanes, alkoxytitaniums and alkoxyzirconiums. 
     
     
         14 . The curable resin composition of  claim 1 , wherein a content of the nonvolatile components accounts for at least 90% by weight. 
     
     
         15 . The curable resin composition of  claim 1 , further comprising a compound capable of suppressing the ene-thiol reaction. 
     
     
         16 . (canceled) 
     
     
         17 . A coated article which has a coating layer on a substrate, wherein the coating layer is prepared by curing the curable resin composition of  claim 1 . 
     
     
         18 . The coated article of  claim 17 , wherein the refractive index of the coating layer is higher than that of the substrate. 
     
     
         19 . (canceled) 
     
     
         20 . (canceled) 
     
     
         21 . (canceled) 
     
     
         22 . A transparent substrate, which is prepared by impregnating the curable resin composition of  claim 1  in glass cloth, and curing the curable resin composition. 
     
     
         23 . The transparent substrate of  claim 22  for an optical waveguide, polarizing plate, liquid crystal panel, EL panel, PDP panel, color filter, optical disk substrate and plastic substrate for liquid crystal cell. 
     
     
         24 . (canceled) 
     
     
         25 . (canceled) 
     
     
         26 . The curable resin composition of  claim 1 , wherein
 the alkoxysilanes (a1) is 3-mercaptopropyltrimethoxysilane;   the compound (B) is at least one kind of compound selected from a group of a bisphenol A-type epoxy resin, bisphenol F-type epoxy resin, hydrogenated bisphenol A-type epoxy resin and alicyclic epoxy resin;   the compound (C) is isophorone diisocyanate;   the compound (D) is an allyl group-containing compound; and   the curable resin composition further comprises alkoxysilanes (a1) and/or the hydrolysate (excluding condensate thereof) (E).   
     
     
         27 . The curable resin composition of  claim 26 , further comprising metal alkoxides (a2) and/or the hydrolysate (excluding condensate thereof) (F). 
     
     
         28 . The curable resin composition of  claim 4 , wherein
 the alkoxysilanes (a1) is 3-mercaptopropyltrimethoxysilane;   the compound (D) is an allyl group-containing compound; and   the curable resin composition further comprising:
 alkoxysilanes (a1) and/or the hydrolysate (excluding condensate thereof) (E); and 
 metal alkoxides (a2) and/or the hydrolysate (excluding condensate thereof) (F).