Patent DE-102008036495-A1 (DE)
Title: New naphthalene, perylene, benzoperylene, terrylene, quaterrylene bisimide and trisimide anions, as salts, e.g. tetrabutylammonium- or potassium-salts, useful e.g. to prepare dyes, preferably vats dye, to color cotton, paper and nylon
Inventor: LANGHALS HEINZ
IPC: C07D471/06
Filed: 2008-08-04
Abstract: Naphthalene bisimide radical anions (XVI), naphthalene bisimide anions (XVII), perylene bisimide radical anions (XVIII), perylene bisimide anions (XIX), benzoperylene trisimide radical anions (XX), benzoperylene trisimide anions (XXI), terrylene bisimide radical anions (XXII), terrylene bisimide anions (XXIII), quaterrylene bisimide radical anions (XXIV), and quaterrylene bisimide anions (XXV), as salts e.g. tetrabutylammonium salt, or as salts with other cation, as counter ion e.g. lithium salt, or mono-, di- and trialkylammonium salt, are new. Naphthalene bisimide radical anions of formula (XVI), naphthalene bisimide bisanions of formula (XVII), perylene bisimide radical anions of formula (XVIII), perylene bisimide anions of formula (XIX), benzoperylene trisimide radical anions of formula (XX), benzoperylene trisimide anions of formula (XXI), terrylene bisimide radical anions of formula (XXII), terrylene bisimide anions of formula (XXIII), quaterrylene bisimide radical anions of formula (XXIV), and quaterrylene bisimide anions of formula (XXV), as salts, preferably as tetrabutylammonium salt, or as salts with other cation, as counter ion, such as lithium, sodium, potassium, rubidium, cesium salt or ammonium salt, mono-, di- and trialkylammonium salt or H +>, H 3O +>or other hydrated proton or protonated forms, are new. R 1>-R 1>4>H or linear alkyl with at least 1-37C ((in which 1-10 CH 2-units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups (in which one CH unit is optionally substituted by N)), -C?=C-, 1,2-, 1,3- or 1,4-substituted phenyl residue, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-disubstituted pyridine residue, 2,3-, 2,4-, 2,5- or 3,4-disubstituted thiophene residue, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-disubstituted napthalene residue (in which one or two CH groups 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 residue (in which one or two CH groups are optionally substituted by N), where 2-12 single hydrogen atoms of the CH 2group in the alkyl residue are optionally substituted by halo, preferably F, Cl, Br or I or CN), or linear 2-18C-alkyl (in which 1-6 CH 2units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups (in which one 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 (in 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 (in which one or two carbon atoms are optionally substituted by N), where 2-12 single hydrogen atoms of the CH 2-group of the alkyl residue are optionally substituted by halo, preferably F, Cl, Br or I, or CN), or linear 2-18C-alkyl (in which 1-6 CH 2-units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups (in which one 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 (in 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 (in which one or two carbon atoms are optionally substituted by N), where: instead carrying substituents, the free valent methine group and/or quaternary carbon atom are connected in pair-wise to form rings, e.g. cyclohexane ring, and the residue R 1>-R 6>contains halo, preferably F, Cl, Br or I). Independent claims are included for: (1) a dye comprising (XIV)-(XXV), in which quaternary ammonium salt is used as counter cation, which is four times alkylated ammonium salt, preferably strong ammonium salt with four alkyl group, optionally branched iso-propyl group, benzyl group or branched n-alkyl group, tetra-n-butyl ammonium; and (2) the preparations of (XIV)-(XXV). [Image] [Image] [Image] [Image].