Patent DE-19709008-A1 (DE)
Title: Perylene tetra:carbimide dyes and fluorescent dyes and pigments forming metal complexes
Inventor: LANGHALS HEINZ PROF DR
IPC: C09B5/62
Filed: 1997-03-05
Abstract: Perylene-3,4:9,10-tetracarbimides (I; n = 2-10) and dyes (II), (IV), (V), (VI) and (VII) of formula (A) and dyes of formula (III) are new; in which (I) Q<1> = R<1> and Q<2> = a group of formula (B); (II) Q<1> = R<1> and Q<2> = a group of formula (C); (IV) Q<1> = R<1> and Q<2> = 8-hydroxyquinolin-5-yl; (V) Q<1> = R<1> and Q<2> = 1,10-phenanthrolin-5-yl; (VI) Q<1>, Q<2> = a (B) group; (VII) Q<1> = a group of formula (D) and Q<2> = a (C) group; R<1>-R<9> = H or 1-9 groups, e.g. isocyclic aromatic groups, preferably mono- to tetracyclic, especially mono- or bicyclic groups (e.g. phenyl, diphenyl or naphthyl); or R<1>-R<9> = H and 1-4 groups T; or R<1> or R<9> = a heterocyclic aromatic group, which preferably is mono- to tri-cyclic and may be purely heterocyclic or have condensed benzene ring(s) (e.g. pyr(im)idyl, pyrazinyl, triazinyl, furyl, pyrrolyl, thiophenyl, (iso)quinolyl, coumarinyl, (benz)imidazolyl, (benz)oxazolyl, (di)benzofuranyl, (di)benzothiophenyl, indolyl, carbazolyl, pyr azolyl, (benz)isox azolyl, (benzo)thiazolyl, indazolyl, pyridazinyl, cinnolyl, quinazolyl, quinoxalyl, phthalazinyl, phthalazindionyl, phthalimidyl, chromonyl, naphtholactamyl, benzopyridonyl, ortho-sulphobenzimidyl, maleimidyl, naphtharidinyl, benzimidazolonyl, benzoxazolonyl, benzothiazolonyl, benzothiazolinyl, quinazolonyl, quinoxalonyl, phthalazonyl, dioxapyrinidinyl, pyridonyl, isoquinolonyl, (benz)isothiazolyl, indazolonyl, acridinyl, acridonyl, quinazolindionyl, benzoxazin(di)onyl and phthalimidyl); the isocyclic and heterocyclic aromatic groups may have usual non-water-solubilising substituents, e.g. T; T = (a) halogen, e.g. Cl, Br, I or F; (b) 1-18, preferably 1-12, especially 1-8, more especially 1-4C alkyl; (c) -OR<13>; (e) CN; (f) -N(R<14>)(R<15>); (g) -COR<16>; (h) -N(R<17>)COR<18>; (i) -N(R<19>)COOR<20>; (j) -N(R<21>)CON(R<22>)(R<23>); (k) -NHSO2R<24>; (l) -SO2R<25> or -SOR<25>; (m) -SO2R<26>; (n) -CON(R<27>)(R<28>); (o) -SO2N(R<29>)(R<30>); (p) -N=N-R<31>; (q) -OCOR<32>; or (r) -CONHR<33>; (b) optionally have non-water-solubilising substituents, e.g. F, OH, CN, -OCOR<10>, -OR<10>, -OCOOR<10>, CON(R<11>)(R<12>), -OCONHR<11>, mono- or dialkylamino, aryl (e.g. naphthyl or especially phenyl, optionally substituted by halogen, alkyl or -O-alkyl) or heteroaryl (e.g. 2-thienyl, 2-benzoxazolyl, 2-benzothiazolyl, 2-benzimidazolyl, 6-benzimidazolonyl, 2-, 3- or 4-pyridinyl, 2-, 4- or 6-quinolyl or 1-, 3-, 4-, 6- or 8-isoquinolyl); R<10> = alkyl, aryl, e.g. naphthyl or benzyl, optionally substituted by halogen, alkyl or -O-alkyl, or heterocyclyl; R<11>, R<12> = H, alkyl, optionally substituted by CN or OH, 3-24 C, especially 5-, 6-, 12-, 15-, 16-, 20- or 24-C cycloalkyl or (hetero)aryl, especially phenyl, optionally substituted by halogen, alkyl or -O-alkyl; or R<10>, R<11> and one of R<1>-R<9> = a group completing a 5-6-membered (hetero)ring; any alkyl substituents have 1-18, preferably 1-12, especially 1-8, more especially 1-4 C; R<13> = H, alkyl, aryl (e.g. naphthyl or especially unsubstituted phenyl), 3-24, e.g. 5-, 6-, 12-, 15-, 16-, 20- or 24-C cycloalkyl or (hetero)aryl, especially phenyl, optionally substituted by halogen, alkyl or O-alkyl (optionally with substituents as in (b)); R<14>, R<15>, R<17>, R<18>, R<24>-R<30>, R<32> = as in (b); R<19>-R<23> = as in (b) or (c); R<16>, R<33> = as in (a); R<31> = the residue of a coupling component or phenyl, optionally substituted by halogen, alkyl or -O-alkyl. Numerous examples of suitable substituents are cited.