The present invention relates to fluorine compounds (I), (II) and (III), to processes for the preparation thereof, and to the use thereof.

It is an issue to provide an epoxy resin that has excellent fluidity and curability, that provides a cured product with favorable moisture resistance and mechanical strength, and that is suitable for use in a semiconductor sealing material, a circuit board, and the like, to provide a method for producing the epoxy resin, and to provide an epoxy resin composition containing the epoxy resin and a cured product of the epoxy resin composition. Specifically, an epoxy resin that is epoxy resin (A) primarily containing epoxidized dihydroxybenzene in which an alkyl group having a carbon number of 1 to 8 may be included as a substituent on an aromatic ring, wherein the area ratio of the maximum peak in GPC measurement is 90% or more, a method for producing the epoxy resin, an epoxy resin composition containing the epoxy resin, and a cured product of the epoxy resin composition are provided.

A method of producing functionalized graphene oxide includes mixing graphene oxide with a reactive monomer containing at least one epoxy functional group and a secondary functional group that is selected from vinyl, acrylate, methacrylate, and epoxy to form a mixture, adding an activation agent, heating and stirring the mixture, cooling the mixture, separating the particles from the mixture, and drying the particles to produce functionalized graphene oxide. A method of manufacturing a cured polymer resin using functionalized graphene oxide includes mixing functionalized graphene oxide with a resin precursor to produce a functionalized graphene mixture, wherein the particles contain functional groups nearly identical to, or identical to, a polymer precursor material, adding a curing initiator to the functionalized graphene mixture and mixing to produce a formulation, depositing the formulation into a desired shape, and curing the formulation to form a polymer having functionalized graphene oxide groups in a base polymer material.

A method of producing functionalized graphene oxide includes mixing graphene oxide with a reactive monomer containing at least one epoxy functional group and a secondary functional group that is selected from vinyl, acrylate, methacrylate, and epoxy to form a mixture, adding an activation agent, heating and stirring the mixture, cooling the mixture, separating the particles from the mixture, and drying the particles to produce functionalized graphene oxide. A method of manufacturing a cured polymer resin using functionalized graphene oxide includes mixing functionalized graphene oxide with a resin precursor to produce a functionalized graphene mixture, wherein the particles contain functional groups nearly identical to, or identical to, a polymer precursor material, adding a curing initiator to the functionalized graphene mixture and mixing to produce a formulation, depositing the formulation into a desired shape, and curing the formulation to form a polymer having functionalized graphene oxide groups in a base polymer material.

A polyphenylene ether oligomer and a polyphenylene ether oligomer are provided. The polyphenylene ether oligomer has a structure represented by Formula (I): ##STR00001## wherein each R.sup.1 can be independently hydrogen, C.sub.1-6 alkyl group, or phenyl group; each R.sup.2 can be independently hydrogen, C.sub.1-6 alkyl group, or phenyl group; a:(a+b) is from 0.05:1 to 1:1; n:(a+b) is from 0.05:1 to 5:1; Q can be ##STR00002##
m can be 0 or an integer from 1 to 4; Ra can be C.sub.1-6 alkylene group; Rb can be C.sub.1-6 alkylene group; each X is independently hydrogen, acryloyl group, allyl group, vinylbenzyl group, epoxypropyl group, methacryloyl group, propargyl group, or cyanol group; and wherein the polyphenylene ether oligomer can have a number average molecular weight from 400 to 2,000.

A polyphenylene ether oligomer and a polyphenylene ether oligomer are provided. The polyphenylene ether oligomer has a structure represented by Formula (I): ##STR00001## wherein each R.sup.1 can be independently hydrogen, C.sub.1-6 alkyl group, or phenyl group; each R.sup.2 can be independently hydrogen, C.sub.1-6 alkyl group, or phenyl group; a:(a+b) is from 0.05:1 to 1:1; n:(a+b) is from 0.05:1 to 5:1; Q can be ##STR00002##
m can be 0 or an integer from 1 to 4; Ra can be C.sub.1-6 alkylene group; Rb can be C.sub.1-6 alkylene group; each X is independently hydrogen, acryloyl group, allyl group, vinylbenzyl group, epoxypropyl group, methacryloyl group, propargyl group, or cyanol group; and wherein the polyphenylene ether oligomer can have a number average molecular weight from 400 to 2,000.

A method of manufacturing a cured polymer resin using functionalized graphene oxide, includes mixing functionalized graphene oxide with a resin precursor and an optional solvent to produce a functionalized graphene solution wherein the particles contain functional groups nearly identical to, or identical to, a polymer precursor material, adding a curing initiator to the resin solution and mixing to produce a resin solution, depositing the formulation into a desired shape, and curing the formulation to form a polymer having functionalized graphene oxide groups in a base polymer material. A method of producing functionalized graphene oxide includes dispersing graphene oxide into a solvent to produce dispersed graphene oxide, mixing the dispersed graphene oxide with a reactive molecule containing at least one epoxy functional group and a secondary functional group that is selected from vinyl, acrylate, methacrylate and epoxy to form a solution, adding an activation agent, heating and stirring the solution, cooling the solution, separating the particles from solution, and drying the particles to produce functionalized graphene oxide. A composition of matter includes exfoliated, functionalized graphene oxide particles, a curing initiator, a polymer precursor material, wherein the particles contain functional groups nearly identical to, or identical to, a polymer precursor material.

A method of manufacturing a cured polymer resin using functionalized graphene oxide, includes mixing functionalized graphene oxide with a resin precursor and an optional solvent to produce a functionalized graphene solution wherein the particles contain functional groups nearly identical to, or identical to, a polymer precursor material, adding a curing initiator to the resin solution and mixing to produce a resin solution, depositing the formulation into a desired shape, and curing the formulation to form a polymer having functionalized graphene oxide groups in a base polymer material. A method of producing functionalized graphene oxide includes dispersing graphene oxide into a solvent to produce dispersed graphene oxide, mixing the dispersed graphene oxide with a reactive molecule containing at least one epoxy functional group and a secondary functional group that is selected from vinyl, acrylate, methacrylate and epoxy to form a solution, adding an activation agent, heating and stirring the solution, cooling the solution, separating the particles from solution, and drying the particles to produce functionalized graphene oxide. A composition of matter includes exfoliated, functionalized graphene oxide particles, a curing initiator, a polymer precursor material, wherein the particles contain functional groups nearly identical to, or identical to, a polymer precursor material.

Enantiomers of butanediol diglycidyl ether (BDDE) are present in an enantiomerically enriched enantioenriched mixture of BDDE stereisomers or in an enantiomerically pure BDDE. Enantiomerically enriched or pure BDDE is useful as a cross-linking agent, such as in the preparation of a cross-linked hyaluronic acid product.

Enantiomers of butanediol diglycidyl ether (BDDE) are present in an enantiomerically enriched enantioenriched mixture of BDDE stereisomers or in an enantiomerically pure BDDE. Enantiomerically enriched or pure BDDE is useful as a cross-linking agent, such as in the preparation of a cross-linked hyaluronic acid product.