This fluorine-containing ether compound is represented by Formula (1).

R.sup.1—R.sup.2—CH.sub.2—R.sup.3—CH.sub.2—R.sup.4—R.sup.5  (1) (in Formula (1), R.sup.1 is an aryl group or an aralkyl group, R.sup.2 is a divalent linking group having 0 or 1 polar group, R.sup.3 is a perfluoropolyether chain, R.sup.4 is a divalent linking group having 2 or 3 polar groups, and R.sup.5 is an aryl group or an aralkyl group.)

This fluorine-containing ether compound is represented by Formula (1).

R.sup.1—R.sup.2—CH.sub.2—R.sup.3—CH.sub.2—R.sup.4—R.sup.5  (1) (in Formula (1), R.sup.1 is an aryl group or an aralkyl group, R.sup.2 is a divalent linking group having 0 or 1 polar group, R.sup.3 is a perfluoropolyether chain, R.sup.4 is a divalent linking group having 2 or 3 polar groups, and R.sup.5 is an aryl group or an aralkyl group.)

A multi-epoxidized biphenyl compound has the formula (I) below ##STR00001##
wherein R, R.sub.1, R.sub.2 and R.sub.3 are as defined in the description, as well as mixtures of at least two of the compounds. These multi-epoxidized biphenyl compounds are fully suitable as main constituents of thermosetting epoxy resins, i.e. as polyepoxides precursors. They are beneficial substitutes for bisphenol A diglycidyl ether.

A multi-epoxidized biphenyl compound has the formula (I) below ##STR00001##
wherein R, R.sub.1, R.sub.2 and R.sub.3 are as defined in the description, as well as mixtures of at least two of the compounds. These multi-epoxidized biphenyl compounds are fully suitable as main constituents of thermosetting epoxy resins, i.e. as polyepoxides precursors. They are beneficial substitutes for bisphenol A diglycidyl ether.

A fluorine-containing ether compound represented by a formula (1) shown below.

R.sup.1—(O(CH.sub.2).sub.a).sub.b-[A]-[B]—O—CH.sub.2—R.sup.2—CH.sub.2—R.sup.3  (1)

(In the formula (1), R.sup.1 is an alkyl group which may have a substituent, or an organic group having at least one double bond or triple bond. Further, a represents an integer of 2 to 4, and b is 0 or 1. [A] is represented by a formula (2): —(OCH.sub.2CH(OH)CH.sub.2).sub.c— (wherein c is 1 or 2). [B] is represented by a formula (3): —(O(CH.sub.2).sub.eCH(OH)CH.sub.2).sub.d— (wherein d is 0 or 1, and e represents an integer of 2 to 4). However, the sum of c in the formula (2) and d in the formula (3) is 2. R.sup.2 is a perfluoropolyether chain. R.sup.3 is represented by a formula (4): —(OCH.sub.2CH(OH)CH.sub.2).sub.2—O—CH.sub.2(CH.sub.2).sub.fOH (wherein f represents an integer of 2 to 5).

A fluorine-containing ether compound represented by a formula (1) shown below.

R.sup.1—(O(CH.sub.2).sub.a).sub.b-[A]-[B]—O—CH.sub.2—R.sup.2—CH.sub.2—R.sup.3  (1)

(In the formula (1), R.sup.1 is an alkyl group which may have a substituent, or an organic group having at least one double bond or triple bond. Further, a represents an integer of 2 to 4, and b is 0 or 1. [A] is represented by a formula (2): —(OCH.sub.2CH(OH)CH.sub.2).sub.c— (wherein c is 1 or 2). [B] is represented by a formula (3): —(O(CH.sub.2).sub.eCH(OH)CH.sub.2).sub.d— (wherein d is 0 or 1, and e represents an integer of 2 to 4). However, the sum of c in the formula (2) and d in the formula (3) is 2. R.sup.2 is a perfluoropolyether chain. R.sup.3 is represented by a formula (4): —(OCH.sub.2CH(OH)CH.sub.2).sub.2—O—CH.sub.2(CH.sub.2).sub.fOH (wherein f represents an integer of 2 to 5).

A polyvalent glycidyl compound is produced from a compound having one or more 2-alkenyl ether groups and two or more 2-alkenyl groups using a hydrogen peroxide aqueous solution as an oxidizing agent to oxidize the 2-alkenyl ether groups and the 2-alkenyl groups. A 2-alkenyl ether compound having two or more (un)substituted 2-alkenyl groups and one or more (un)substituted 2-alkenyl ether groups is oxidized using a hydrogen peroxide aqueous solution as an oxidizing agent in the presence of a tungsten compound and a quaternary ammonium salt as catalysts and of phosphoric acid as a co-catalyst, while controlling the pH of the reaction solution to 1.0-4.0 using an acid other than phosphoric acid. During the oxidation, the step of adding the hydrogen peroxide aqueous solution to the reaction solution and the step of adding the acid other than phosphoric acid thereto are alternately repeated at intervals two or more times.

The present invention relates to a process for preparing a compound having the formula (I), said process comprising the following steps: a) the addition of an oxygen source into a solution of a compound of formula (II), in a water-miscible solvent, b) the addition of a laccase in the solution obtained after step a); and c) the possible recovering of the compound of formula (I) thus obtained.

##STR00001##

Provided are an electrophotographic photosensitive member which satisfies wear resistance and electrical characteristics, and in which image deletion is satisfactorily suppressed, and a process cartridge and an electrophotographic apparatus each including the electrophotographic photosensitive member. The electrophotographic photosensitive member comprises a surface layer which includes a polymerized product of a hole transporting substance having a reactive functional group, in which a structure other than the reactive functional group of the hole transporting substance is one of: a structure consisting of a carbon atom and a hydrogen atom; and a structure consisting of a carbon atom, a hydrogen atom and an oxygen atom, and the structure other than the reactive functional group of the hole transporting substance comprises a specific conjugate structure.

Provided are an electrophotographic photosensitive member which satisfies wear resistance and electrical characteristics, and in which image deletion is satisfactorily suppressed, and a process cartridge and an electrophotographic apparatus each including the electrophotographic photosensitive member. The electrophotographic photosensitive member comprises a surface layer which includes a polymerized product of a hole transporting substance having a reactive functional group, in which a structure other than the reactive functional group of the hole transporting substance is one of: a structure consisting of a carbon atom and a hydrogen atom; and a structure consisting of a carbon atom, a hydrogen atom and an oxygen atom, and the structure other than the reactive functional group of the hole transporting substance comprises a specific conjugate structure.