Patent DE-102007063051-A1 (DE)
Title: New perylene bisimide compounds useful as pigments for glue-, aquarel- and water- colors, for mass coloring of polymers, preferably e.g. polyvinyl chloride, polyacrylic acid and/or their copolymers and in display elements of sign boards
Inventor: LANGHALS HEINZ
IPC: C07D471/06
Filed: 2007-12-28
Abstract: Perylene bisimide compounds (Q) are new. Perylene bisimide compounds (Q) of formula (I) or (II) are new. R 5>-R 5>H or 37C-alkyl residue, where 1-10 CH 2-units are optionally substituted by carbonyl groups, O, S, Se, Te, cis or trans-CH=CH-groups, where one CH unit is optionally substituted by N, C?=C, 1,2-, 1,3 - or 1,4-substituted phenyl residues, 2,3, 2,4, 2,5, 2,6, 3,4 - or 3,5-disubstituted pyridine residues, 2,3, 2,4, 2,5 or 3,4-disubstituted thiophene residues, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8, 2,3, 2,6 or 2,7-disubstituted naphthalene residues, where one or two groups of CH 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 residues, where one or two CH groups are optionally substituted by N, up to 12 H atoms of CH 2-groups are optionally substituted on the same carbon atoms by halogens, CN or up to 18C-alkyl, where 1-6 CH 2-units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, where one CH-unit is optionally substituted by N, C?=C, 1,2, 1,3 or 1,4-substituted phenyl residues, 2,3, 2,4, 2,5, 2,6, 3,4- or 3,5-disubstituted pyridine residues, 2,3, 2,4, 2,5- or 3,4-disubstituted thiophene residues, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8, 2,3, 2,6- or 2,7-disubstituted naphthalene residues, where 1-2C 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 residues, where 1-2C are optionally substituted by N, up to 12 H of the CH 2of the alkyl residues are optionally substituted on the same carbon atoms by halogen, CN or up to 18C-alkyl, where 1-6 CH 2-units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, where one CH-unit is optionally substituted by N, C?=C groups, 1,2, 1,3- or 1,4-substituted phenyl residues, 2,3, 2,4, 2, 5, 2,6, 3,4- or 3,5-disubstituted pyridine residues, 2,3, 2,4, 2,5- or 3,4-disubstituted thiophene residues, 1,2, 1,3, 1,4, 1,5, 1,6, 1,7, 1,8-2,3, 2,6- or 2,7-disubstituted naphthalene residues, where 1-2C 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 residues, where 1-2C are optionally substituted by N, up to 12 single hydrogen atoms of the CH 2groups are replaced by F, Cl, Br or I, CN or up to 18C-alkyl, in which 1-6 CH 2units are replaced by carbonyl, O, S, Se, Te, cis or trans -CH = CH-groups, with which one CH unit is optionally replaced also by N, C?=C-groups, 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 replaced 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 N, where up to 12 single H of CH 2-group of the alkyl is substituted by F, Cl, Br or I or CN or linear up to 18C-alkyl, with which 1-6 CH 2-units are replaced by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, with which a CH unit optionally substituted by N, acetylenic C?=C-groups 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 C atoms are replaced 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 C are replaced by N; and X : a spacer group. Provided that: instead of the substituents, the free valences of the methyne groups and/or the quaternary carbon-atoms are linked in pairs, to form a ring, e.g. cyclohexane ring, and the R 1>-R 5>residues further contain F, Cl, Br or I. [Image].