Patent DE-102012008287-A1 (DE)
Title: New imidazoloterrylene bisimide compounds, useful as e.g. pigments and colorants for dyeing purposes, and in lacquers, preferably synthetic resin lacquers such as acrylic or vinyl resins, polyester lacquers and novolak resins
Inventor: LANGHALS HEINZ
IPC: C09B5/62
Filed: 2012-04-16
Abstract: Imidazoloterrylene bisimide compounds are new. Imidazoloterrylene bisimide compounds of formula (I) are new. R1-R18 : H or linear alkyl having at least one carbon atom or less than 37 carbon atom, in which up to 1-10 CH 2-units are optionally replaced by carbonyl, O, S, Se, Te, cis- or trans-CH=CH-groups, where CH-unit is optionally replaced by Q, 12 single H of the CH 2-groups are replaced by F, Cl, Br or I or CN, or linear 18C-alkyl, 1-6 CH 2-units are optionally replaced by T, 12 single H of the CH 2 groups of the alkyl are optionally replaced by F, Cl, Br or I or CN or linear 18C-alkyl, and 1-6 CH 2-units are independently replaced by T; Q : N, acetylenic-CC-, 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 or 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 CH-groups are optionally 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 CH-groups are optionally replaced by N; T : carbonyl, O, S, Se, Te, cis- or trans-CH=CH-groups, and CH-unit is optionally replaced by N, acetylenic -CC-, 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 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 carbon atoms are optionally replaced by N), where substituents carrying the free valency of methine group and quaternary C atoms are pair-wise coupled to form a ring e.g. cyclohexane ring; R1-R9 : halo including F, Cl, Br or I; and X : linear alkyl having at least one carbon atom or less than 37 carbon atom, where up to 1-10 CH 2-units are optionally replaced by carbonyl, O, S, Se, Te, cis-or trans-CH=CH group and the CH-unit is replaced by Q, 12 single H of the CH 2-groups are optionally replaced by F, Cl, Br or I or CN, or linear 18C-alkyl, 1-6 CH 2-units are optionally replaced by T, 12 single H of the CH 2 groups of the alkyl radical are optionally replaced by F, Cl, Br or I or CN or linear 18C-alkyl, and 1-6 CH 2-units are optionally replaced by T. Independent claims are included for: (1) preparation of (I); and (2) temperature measurement using temperature dependence of UV/visible-absorptions-, fluorescence and fluorescence excitation spectra, preferably fluorescence spectra of imidazole terrylene compound of formula (II) and of perylene bisimides compound of formula (III), where the spectra show a maximum displacement of the fluorescence. [Image] [Image].