41680-76-6

The invention relates to the field of synthesis of organic pigments and discloses a preparation method for quinacridone and derivatives of the quinacridone. The preparation method comprises the steps that dimethyl succinate generates sodium dimethyl succinylsuccinate (DMSS) through cyclic condensation under an effect of sodium methoxide, and then being acidized into DMSS; condensation reaction occurs between the DMSS and aniline or substituted aniline, an intermediate product generated during condensation is directly oxidized and dehydrogenated by sodium 3-nitrobenzene sulfonate to obtain an oxidative product; and finally coarse products of the quinacridone or the derivatives of the quinacridone are prepared from the oxidative product in a ring-closing mode under an effect of polyphosphoric acid, and finally finished products of the quinacridone or the derivatives of the quinacridone are obtained through pigmentation treatment.

The invention relates to a method for preparing 2,5-di(substituted) arylamino terephthalic acid by oxidizing 2,5-di(substituted) arylamino-3,6-dihydro-terephthalic acid ester. Hydrogen peroxide is adopted as an oxidizing agent in the method; the hydrogen peroxide is capable of completely oxidizing matter to be oxidized (the reactant conversion rate is high), and has better selectivity (the purity and the yield of a target object are both higher); furthermore, the hydrogen peroxide is converted into water after being oxidized, and a reaction system has no byproducts formed by over oxidation. Therefore, the method for preparing the 2,5-di(substituted) arylamino terephthalic acid, provided by the invention, is economic, friendly to environment and easy to control in reaction.

2,5-di(p-methoxyanilino)terephthalic acid crystal types I and Il are made by controlling the pH during the recovery of the oxidized product of the condensation of dimethylsuccinyl succinate with p-methoxyaniline. The resulting 2,5-di(p- methoxyanilino)-terephthalic acid can be converted into 2,9-dimethoxyquinacridone or a solid solution thereof having controlled characteristics.

The present invention relates to a novel quinacridone pigment compositions, a process using a mixed amine synthesis for the ultimate production of the compositions and to their use as colorants for pigmenting high molecular weight organic materials.

Disclosed are new quinacridone dye derivatives having characteristic fluorescence lifetimes. Also disclosed are methods for labelling target biological materials employing the quinacridone dyes and use of the labelled materials in biological assays. The quinacridone derivatives have the structure (I), in which Z1 and Z2 independently represent the atoms necessary to complete one ring, two fused ring, or three fused ring aromatic or heteroaromatic systems, each ring having five or six atoms selected from carbon atoms and optionally no more than two atoms selected from oxygen, nitrogen and sulphur; R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, halogen, amide, hydroxyl, cyano, nitro, mono- or di-nitro-substituted benzyl, amino, mono- or di-C1-C4 alkyl-substituted amino, sulphydryl, carbonyl, carboxyl, C1-C6 alkoxy, acrylate, vinyl, styryl, aryl, heteroaryl, C1-C20 alkyl, aralkyl, sulphonate, sulphonic acid, quaternary ammonium, the group —E—F and the group —(CH2—)nY; R1 and R2 are independently selected from hydrogen, mono- or di-nitro-substituted benzyl, C1-C20 alkyl, aralkyl, the group —E—F and the group —(CH2—)nY; E is a spacer group, F is a target bonding group; Y is selected from sulphonate, sulphate, phosphonate, phosphate, quaternary ammonium and carboxyl; and n is an integer from 1 to 6. The invention also relates to a set of different fluorescent quinacridone dye derivatives, each dye having a different fluorescence lifetime, the set of dyes being particularly useful for multiparameter analysis. 1

A process for producing 2,5-di(arylamino)-3,6-dihydroterephthalic acid dialkyl ester having a high purity from 1,4-cyclohexanedione-2,5-di(carboxylic acid alkyl ester) at high yields for a short period of time; a process for producing quinacridone of which the byproduct content is small, from the above 2,5-di(arylamino)-3,6-dihydroterephthalic acid dialkyl ester; and a process for producing quinacridone of which the particle diameter is adjusted as desired, from the above 2,5-di(arylamino)-3,6-dihydroterephthalic acid dialkyl ester without adding a step of forming a pigment.

A process for the preparation of 2,5-diarylaminoterephthalic acids by oxidation of 2,5-diarylamino-3,6-dihydroterephthalic acid esters using oxygen or oxygen-containing gases, preferably air, in alcoholic-alkaline or alcoholic-aqueous-alkaline solution or suspension in the presence of an oxygen-transferring agent and working up to give the 2,5-diarylaminoterephthalic acids, characterized in that the oxidation is carried out in the presence of quaternary ammonium compound.