Patent DE-102005060074-A1 (DE)
Title: New perylene dye compounds useful, e.g. as a pigment for adhesive dye, vats and corrosion dye for coloring natural materials, an initial material for super conductive organic material, and in coating materials and lacquers
Inventor: LANGHALS HEINZ
IPC: C09B5/62
Filed: 2005-12-15
Abstract: Perylene dye compounds (A), are new. Perylene dye compounds (A) of formulae (I) and (II), are new. R1>-R12>, X : H or at least and at most 37C-alkyl, with which 1-10 CH2 is substituted by carbonyl, O, S, Se, Te, cis or trans CH=CH, in which the CH unit is optionally substituted by N, C?=C, 1,2-, 1,3- or 1,4- substituted phenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5- disubstituted pyridine, 2,3-, 2,4-, 2,5- or 3,4- disubstituted thiophene, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7- disubstituted naphthalene, with which one or two CH is optionally substituted by N, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10-disubstituted anthracene, with which one or two CH groups are optionally substituted N, up to 12 H atoms of the CH2 is optionally substituted by halo, CN or a linear up to 18C-alkyl, in which 1-6 CH2 is optionally substituted by carbonyl, O, S, Se, Te, cis or trans CH=CH-, with which CH is optionally substituted by N, C?=C, 1,2-, 1,3- or 1,4-substituted phenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-disubstituted pyridine, 2,3-, 2,4-, 2,5- or 3,4-disubstituted thiophene, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7- disubstituted naphthalene, in which one or two carbon atoms are optionally substituted by N or 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10-disubstituted anthracene with which one or two carbon atoms are optionally substituted by N, up to 12 H of the CH2- of the alkyl is optionally substituted by halo, CN or up to 18C-linear alkyl, with which 1-6 CH2 is optionally substituted by carbonyl, O, S, Se, Te, cis or trans CH=CH-, with which a CH is optionally substituted by N, C?=C, 1,2-, 1,3- or 1,4-substituted phenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-disubstituted pyridine, 2,3-, 2, 4-, 2,5- or 3,4-disubstituted thiophene, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, 2,7 disubstituted naphthalene, with which one or two carbon atoms are optionally substituted by N, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10 -disubstituted anthracene, with which one or two carbon atoms are optionally substituted by N. Where, instead of the substitutents the free valency of methine group and/or quaternary carbon atoms is bonded in pairs to obtain a ring such as cyclohexane ring. Independent claims are included for: (1) a method for the preparation of an amine compound (14) of formula (CH2=CH2-X-C(R1>)(R2>)-CH2-NH2) comprising reducing a nitrile compound (15) of formula (CH2-CH2-X-C(R1>)(R2>)-C?=N) using a reducing agent such as complex hydrides e.g. lithium aluminum hydride, sodium aluminum bis-(2-methoxyethoxo)dihydride or H, and catalyst such as noble metal catalysts e.g. platinum, palladium, rhodium and its compound, or copper chromite, or by electro-chemical reduction; and (2) a method for the preparation of nitrile compound (15) comprising alkylating the unsaturated nitrile using strong base such as lithium bistrimethylsilyl amide, sodium amide, potassium amide, sodium hydride, potassium hydride or potassium-tert-butylate also in combination with strong non-ionic bases such as 1,8-diazabicyclo-[5.4.0]-undec-7-ene or 1,5-diazabicyclo[4.3.0]non-5-ene, where the alkylating agent is an alkylhalo ester of sulfuric acid, toluol sulfuric acid or ester of phosphoric acid. [Image] [Image].