Described herein are articles and methods of making articles, including a transparent composite film having a fiber filler embedded in a polymer network. The polymer network of the transparent composite film is a cured, cross-linked matrix including a first and second structure segment. The structure segments may contribute or impart improved properties in the transparent composite film. The select structure segments can provide increased modulus and reduced glass transition temperature thereby allowing for a desirable balance of flexibility and rigidity in the transparent composite film. The improved transparent composite film is suitable for many applications including use in display devices.

Compounds of formula (I) are photoinitiators or photosensitizers in a photopolymerizable composition:

##STR00001##

R.sub.1 represents a monovalent, linear, branched or cyclic, aliphatic hydrocarbon group having 1 to 20 carbon atoms, optionally substituted with substituent(s) selected from Cl, Br, OH, O, NHCO OR.sub.2, NHCOR.sub.2 or free-radically or ionically polymerizable groups. Each R.sub.2 is independently H or C.sub.1-6 alkyl; n is 1. If n=1, Z and Y are absent and X represents OR.sub.3; if n is >1, Z represents OR.sub.4, Y represents ORs and X represents H or OH. R.sub.3 represents H or R.sub.1; and R.sub.4 and R.sub.5 each independently represent a bivalent hydrocarbon group. The polymerizable moieties as optional substituents of R.sub.1 are polymerizable double or triple bonds, lactam, lactone and epoxide moieties, which are subjectable to ring-opening polymerization; and two of R.sub.1 to R.sub.5 may be linked to one another to form a ring or a dimer.

Compounds of formula (I) are photoinitiators or photosensitizers in a photopolymerizable composition:

##STR00001##

R.sub.1 represents a monovalent, linear, branched or cyclic, aliphatic hydrocarbon group having 1 to 20 carbon atoms, optionally substituted with substituent(s) selected from Cl, Br, OH, O, NHCO OR.sub.2, NHCOR.sub.2 or free-radically or ionically polymerizable groups. Each R.sub.2 is independently H or C.sub.1-6 alkyl; n is 1. If n=1, Z and Y are absent and X represents OR.sub.3; if n is >1, Z represents OR.sub.4, Y represents ORs and X represents H or OH. R.sub.3 represents H or R.sub.1; and R.sub.4 and R.sub.5 each independently represent a bivalent hydrocarbon group. The polymerizable moieties as optional substituents of R.sub.1 are polymerizable double or triple bonds, lactam, lactone and epoxide moieties, which are subjectable to ring-opening polymerization; and two of R.sub.1 to R.sub.5 may be linked to one another to form a ring or a dimer.

According to the present invention, as a monomer which is unlikely to be crystallized in a curable composition for manufacturing an optical member and which enables manufacture of a cured product having a high level of moisture-heat resistance, a compound represented by General Formula (A) is provided.

##STR00001##

In the formula, Ar.sup.11 and Ar.sup.12 each independently represent an aryl group or a heteroaryl group; X.sup.1, Y.sup.1, X.sup.2, Y.sup.2, Z.sup.1, and Z.sup.2 each independently represent a nitrogen atom or a carbon atom, or the like; Ar.sup.13 and Ar.sup.14 each independently represent an arylene group or a heteroarylene group, where at least one of Ar.sup.13 or Ar.sup.14 is a group other than a phenylene group; R.sup.3 to R.sup.6 each independently represent a substituent, q and r each independently are an integer of 0 to 4, and v and w each independently are an integer of 0 or more; L.sup.1 and L.sup.2 each independently represent a single bond, an oxygen atom, an ester bond, or the like; R.sup.11 and R.sup.12 each independently represent a divalent linking group containing a branched alkylene group; and R.sup.21 and R.sup.22 each independently represent a hydrogen atom or a methyl group.

According to the present invention, as a monomer which is unlikely to be crystallized in a curable composition for manufacturing an optical member and which enables manufacture of a cured product having a high level of moisture-heat resistance, a compound represented by General Formula (A) is provided.

##STR00001##

In the formula, Ar.sup.11 and Ar.sup.12 each independently represent an aryl group or a heteroaryl group; X.sup.1, Y.sup.1, X.sup.2, Y.sup.2, Z.sup.1, and Z.sup.2 each independently represent a nitrogen atom or a carbon atom, or the like; Ar.sup.13 and Ar.sup.14 each independently represent an arylene group or a heteroarylene group, where at least one of Ar.sup.13 or Ar.sup.14 is a group other than a phenylene group; R.sup.3 to R.sup.6 each independently represent a substituent, q and r each independently are an integer of 0 to 4, and v and w each independently are an integer of 0 or more; L.sup.1 and L.sup.2 each independently represent a single bond, an oxygen atom, an ester bond, or the like; R.sup.11 and R.sup.12 each independently represent a divalent linking group containing a branched alkylene group; and R.sup.21 and R.sup.22 each independently represent a hydrogen atom or a methyl group.

A preparation method of vinyl ester resin for optimizing heat-release during curing includes: (A) providing a vinyl ester, a solvent and a phase change material to perform mixture; (B) performing a heating process to remove the solvent, so as to obtain a vinyl ester resin containing the phase change material. Thereby, the organic PCM material with high heat absorption and good resin affinity can be used as the temperature control agent of the vinyl ester resin during the curing process for avoiding the defects such as bubbles and cracks being generated in the vinyl ester resin.

A hybrid photosensitive resin having a structure represented by general formula (I) and contains an oxetanyl functional group and a (meth)acryloxy functional group. The functional groups are coordinated with each other and the functionality is adjustable and controllable. The hybrid photosensitive resin is highly suitable for radical-cation photocuring systems, there is no problem of polymerization inhibition by oxygen, and its cured film has high hardness, good flexibility, excellent adherence, and excellent heat resistance.

A hybrid photosensitive resin having a structure represented by general formula (I) and contains an oxetanyl functional group and a (meth)acryloxy functional group. The functional groups are coordinated with each other and the functionality is adjustable and controllable. The hybrid photosensitive resin is highly suitable for radical-cation photocuring systems, there is no problem of polymerization inhibition by oxygen, and its cured film has high hardness, good flexibility, excellent adherence, and excellent heat resistance.

Provided is a method of efficiently producing a solution composition containing a monoetherified product (III) using a hydroquinone compound (I) and a hydroxyl group-containing etherifying agent (II). The method of producing a solution composition includes: a step (1) of reacting a hydroquinone compound (I) and a hydroxyl group-containing etherifying agent (II) in a two-phase system including an alkaline aqueous solution and a hydrophobic ether solvent, and in the absence of a phase transfer catalyst and a hydrophilic organic solvent; and a step (2) of separating and removing an aqueous phase of a two-phase reaction liquid by liquid separation, and washing an organic phase using an aqueous solution containing a neutral inorganic salt and a hydroxide of an alkali metal, or the like.

Provided is a method of efficiently producing a solution composition containing a monoetherified product (III) using a hydroquinone compound (I) and a hydroxyl group-containing etherifying agent (II). The method of producing a solution composition includes: a step (1) of reacting a hydroquinone compound (I) and a hydroxyl group-containing etherifying agent (II) in a two-phase system including an alkaline aqueous solution and a hydrophobic ether solvent, and in the absence of a phase transfer catalyst and a hydrophilic organic solvent; and a step (2) of separating and removing an aqueous phase of a two-phase reaction liquid by liquid separation, and washing an organic phase using an aqueous solution containing a neutral inorganic salt and a hydroxide of an alkali metal, or the like.