Diaryl amines are selectively alkylated by reaction with branched olefins, which olefins are capable of forming tertiary carbonium ions and can be conveniently prepared from readily available branched alcohols. The diaryl amine products are effective antioxidants and often comprise a high amount of di-alkylated diaryl amines and a low amount of tri- and tetra-alkylated diaryl amines.

Diaryl amines are selectively alkylated by reaction with branched olefins, which olefins are capable of forming tertiary carbonium ions and can be conveniently prepared from readily available branched alcohols. The diaryl amine products are effective antioxidants and often comprise a high amount of di-alkylated diaryl amines and a low amount of tri- and tetra-alkylated diaryl amines.

The invention relates to a method for producing diamines and polyamines of the diphenylmethane series, by condensing aniline and formaldehyde followed by an acid-catalysed rearrangement at different production capacities with alteration of the isomer composition in the resulting diamines of the diphenylmethane series (altering the 2,4-MDA content). Adapting the molar ratios of the total used aniline to the total used formaldehyde and of the total used acid catalyst to the total used aniline, and adapting the reaction temperature, allows the rearrangement reaction to be fully completed despite the change in dwell time inevitably associated with a change in production capacity, and allows the formation of undesired by-products to be avoided as far as possible; the intended modification to binuclear content is likewise achieved.

The invention relates to a method for producing diamines and polyamines of the diphenylmethane series, by condensing aniline and formaldehyde followed by an acid-catalysed rearrangement at different production capacities with alteration of the isomer composition in the resulting diamines of the diphenylmethane series (altering the 2,4-MDA content). Adapting the molar ratios of the total used aniline to the total used formaldehyde and of the total used acid catalyst to the total used aniline, and adapting the reaction temperature, allows the rearrangement reaction to be fully completed despite the change in dwell time inevitably associated with a change in production capacity, and allows the formation of undesired by-products to be avoided as far as possible; the intended modification to binuclear content is likewise achieved.

Provided are a donor-acceptor type compound having a novel structure and its use.

An enamine compound represented by general formula (1)

##STR00001##

(in the formula: R.sup.1 represents an electron-withdrawing group; A represents a divalent aromatic hydrocarbon group which may contain a substituent, a divalent aromatic heterocyclic group which may contain a substituent or a divalent unsaturated aliphatic hydrocarbon group which may contain a substituent; R.sup.2 represents a hydrogen atom or a hydrocarbon group which may contain a substituent; R.sup.3 and R.sup.4 are the same or different from each other and represent an aromatic hydrocarbon group which may contain a substituent or an aromatic heterocyclic group which may contain a substituent, or R.sup.3 and R.sup.4 together form an optionally substituted bicyclic aromatic heterocyclic group containing two or more nitrogen atoms or a nitrogen atom and an oxygen atom or a sulfur atom, or a tricyclic aromatic heterocyclic group which may contain a substituent; and R.sup.2 and A, or R.sup.2 and R.sup.3 may together form a cyclic structure).

Provided are a donor-acceptor type compound having a novel structure and its use.

An enamine compound represented by general formula (1)

##STR00001##

(in the formula: R.sup.1 represents an electron-withdrawing group; A represents a divalent aromatic hydrocarbon group which may contain a substituent, a divalent aromatic heterocyclic group which may contain a substituent or a divalent unsaturated aliphatic hydrocarbon group which may contain a substituent; R.sup.2 represents a hydrogen atom or a hydrocarbon group which may contain a substituent; R.sup.3 and R.sup.4 are the same or different from each other and represent an aromatic hydrocarbon group which may contain a substituent or an aromatic heterocyclic group which may contain a substituent, or R.sup.3 and R.sup.4 together form an optionally substituted bicyclic aromatic heterocyclic group containing two or more nitrogen atoms or a nitrogen atom and an oxygen atom or a sulfur atom, or a tricyclic aromatic heterocyclic group which may contain a substituent; and R.sup.2 and A, or R.sup.2 and R.sup.3 may together form a cyclic structure).

Diaryl amines are selectively alkylated by reaction with branched olefins, which olefins are capable of forming tertiary carbonium ions and can be conveniently prepared from readily available branched alcohols. The diaryl amine products are effective antioxidants and often comprise a high amount of di-alkylated diaryl amines and a low amount of tri- and tetra-alkylated diaryl amines.

Diaryl amines are selectively alkylated by reaction with branched olefins, which olefins are capable of forming tertiary carbonium ions and can be conveniently prepared from readily available branched alcohols. The diaryl amine products are effective antioxidants and often comprise a high amount of di-alkylated diaryl amines and a low amount of tri- and tetra-alkylated diaryl amines.

A highly heat-resistant organic compound with favorable hole-transport properties is provided. The organic compound is represented by General Formula (G1). In General Formula (G1), X represents a sulfur atom or an oxygen atom, and R.sup.21 to R.sup.25 and R.sup.27 to R.sup.30 each independently represent any one of hydrogen, halogen, a nitrile group, an alkenyl group, a vinyl group, an alkynyl group, an ethynyl group, a straight-chain alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylsilyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 2 to 30 carbon atoms. Ar.sup.1 represents an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms. Ar.sup.2 is represented by General Formula (G1-1).

##STR00001##

A highly heat-resistant organic compound with favorable hole-transport properties is provided. The organic compound is represented by General Formula (G1). In General Formula (G1), X represents a sulfur atom or an oxygen atom, and R.sup.21 to R.sup.25 and R.sup.27 to R.sup.30 each independently represent any one of hydrogen, halogen, a nitrile group, an alkenyl group, a vinyl group, an alkynyl group, an ethynyl group, a straight-chain alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylsilyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 2 to 30 carbon atoms. Ar.sup.1 represents an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms. Ar.sup.2 is represented by General Formula (G1-1).

##STR00001##