Patent EP-0752494-A1 (EP)
Inventor: GIERA HENRY DR
IPC: C07D277/20
Filed: 1996-06-20
Abstract: Cationic dyes of formula (I), (IV), (VI), (VIII) and anhydro bases e.g. of formula (XII) are new: R<1>, R<3> = -(CH2)n-N(1-4C alkyl)2, hydroxy-, acetoxy-, cyano- or amidocarbonyl-(2-6C)-alkyl, -(CH2)n-O-(CH2)m-OH or -(CH2)n-O-(CH2)m-OCOCH3; R<2> = 1-6C alkyl, benzyl, phenylethyl or R<3> R<4> = H or 1-6C alkyl R<5> = 1-6C alkyl, hydroxy- or acetoxy-(2-6C)-alkyl, -(CH2)n-O-(CH2)m-OH or -(CH2)n-O-(CH2)m-OCOCH3 R<6> = 1-6 C alkyl, benzyl, phenethyl or R<7> R<7> = -(CH2)n-N(1-4C alkyl)2, hydroxy- or amidocarbonyl-(2-6C)-alkyl or -(CH2)n-O-(CH2)m-OH R<8>, R<18> = H or 1-6C alkyl R<9>, R<11> = H, halogen, 1-6C alkyl or 1-6C alkoxy R<10> = 1-6C alkyl, opt. substd. by halogen, CN, OH, 1-4C alkoxy or phenyl R<12>, R<13>, R<14> = 1-6C alkyl, 4-7C cycloalkyl or phenyl gp., opt. substd. by halogen, CN, OH, 1-4C alkoxy or phenyl and R<13>, R<14> may also = H or NR<13>R<14> = pyrrolidino , piperidino or morpholino R<15>, R<16>, R<16>', R<17> = H, halogen, 1-6C alkyl, 1-6C alkoxy, phenoxy, 1-6C alkanoylamino, benzoylamino, 1-6C alkanesulphonylamino, benzenesulphonylamino, CN or NO2 R<19> = H, Me or OMe Z = a bridge of the formula -(CH2)m'-, O, NH, SO2, NHCO, NHCONH, NHSO2NH, NHCOCONH or 1,3,4-oxadiazol-2,5-diyl R<20>, R<21>, R<24>, R<25> = 1-6 C alkyl (opt. substd. by OH, CN or OMe), benzyl, phenyl (opt. substd. by Me, OMe or CN) or tetramethylenesulphonyl and R<20>, R<24> may also = H or NR<20>R<21> and NR<24>R<25> = pyrrolidino, piperidino or morpholino R<22>, R<23> = 1-6C alkyl A = a structure e.g. of formula (XIV) R<26>, R<27> = 1-4C alkyl, opt. substd. by OH, CN or CONH2 R<28> = 1-4 C alkyl (opt. substd. by CN, OH, amido or 1-4C alkoxycarbonyl), benzyl, phenethyl or pyridylethyl R<29>, R<30> = H, 1-4C alkyl, 7-9C aralkyl or 4-7 C cycloalkyl R<31>, R<32> = H, 1-4 C alkyl, 6-10 C aryl, 7-9 C aralkyl or 4-7 C cycloalkyl or CR<31>R<32> = a ring with 5, 6 or more members R<33> = one or more 1-4 C alkyl, 1-4C alkoxy, 7-9C aralkyl, 4-7 C cycloalkyl, halogen, 1-4C alkylcarbonylamino or 1-4C alkylsulphonylamino gps. R<36> = 1-4C alkyl R<34>, R<35> = 1-4C alkyl or 6-10C aryl R<37> = one or more 1-4C alkyl, Cl, Br, 1-4C alkoxy(carbonyl) or 1-4C acylamino gps. R<38>, R<39> = H, 1-6C alkyl, 1-4 C perfluoroalkyl, halogen, NO2, CN, 1-4 C alkoxy(carbonyl), 6-10C aryloxy, 1-4 C alkylcarbonyl(amino), 1-4C dialkylamino, CONH2, 1-4C alkylsulphonyl or 6-10C arylsulphonyl R<40>, R<41> = 1-6C alkyl, opt. substd. by CN, OH, CONH2, 1-4C mono- or dialkylaminocarbonyl, 1-4C alkoxycarbonyl or carboxyl but R<40> and R<41> not both = unsubstd. 1-6C alkyl R<42>, R<43> = H, 1-6C alkyl(carbonyl), 1-4C perfluoroalkyl, halogen, NO2, CN, 1-4C alkoxy(carbonyl) or 6-10C aryloxy R<44>, R<45> = 1-6C alkyl (opt. substd. by CN, OH, CONH2, 1-4C mono- or dialkylaminocarbonyl, 1-4C alkoxycarbonyl, carboxyl or 1-4C alkylsulphonyl) or 6-10C aryl (opt. substd. by 1-6C alkyl, 1-4C perfluoroalkyl, halogen, NO2, CN, 1-4C alkoxy(carbonyl), 6-10C aryloxy, 1-4C alkylcarbonyl, 1-4C dialkylamino, CONH2, ,1-4C alkylsulphonyl or 6-10C arylsulphonyl B = a gp. e.g. of formula (XVI) R<46> = 1-4C alkyl substd. by CN, OH, amido or 1-4C alkoxycarbonyl or 3-sulpholanyl or, if B = a (XIV) gp. and R<52> and/or R<53> = 1-4 C alkyl substd. by OH, CN or CONH2, R<46> may also = 1-4 C alkyl R<47>, R<51> = H, 1-4 C alkyl, 1-4 C alkoxy or halogen R<48>, R<49>, R<50> = H or 1-4C alkyl R<52>, R<53> = H, 1-4C alkyl (opt. substd. by OH, CN or CONH2), 1-4C alkoxy or halogen R<54> = 1-3C alkyl substd. by CN or CONH2, allyl or 3-sulpholanyl or, if R<56> = 1-4C alkyl substd. by OH, CN or CONH2, R<54> may also = 1-4C alkyl, opt. substd. by OH, CN or CONH2 R<55> = H, 1-4C alkyl, 1-4C alkoxy or halogen R<56> = H, 1-4C alkyl (opt. substd. by CN, OH or amido) or 1-4C alkoxy R<57>, R<58> = 1-4C alkyl (opt. substd. by OH, CN or CONH2), benzyl or phenethyl R<59>, R<60> = H, 1-4C alkyl (opt. substd. by CN, OH, amido or 1-4C alkoxycarbonyl), benzyl, phenethyl or phenyl (opt. substd. by Me, OMe, acetylamino or Cl) or NR<59>R<60> = pyrrolidino, piperidino or morpholino R<61> = H, 1-4C alkyl, 1-4C alkoxy, 6C aryl, 5-7C cycloalkyl, halogen, 1-4C alkylcarbonylamino or 1-4C alkylsulphonylamino R<62> = H or cyanoethyl R<63> = 1-4 C alkyl n, m = 2, 3 or 4 m' = 1, 2 or 3 p = 1 or 2 and X<-> = an anion. Also claimed is a method of reducing the toxicity of residual liquors from dyeing with cationic dye(s) by using cationic dyes having a calculated electrostatic screening energy (idealised hydration energy) of at least 50 kcal/mol.