DE2040653C3 - Methine dyes, processes for their production and their use for dyeing certain polymers, copolymers, leather, tannin cotton, printing pastes and fibers containing lignin - Google Patents
Methine dyes, processes for their production and their use for dyeing certain polymers, copolymers, leather, tannin cotton, printing pastes and fibers containing ligninInfo
- Publication number
- DE2040653C3 DE2040653C3 DE19702040653 DE2040653A DE2040653C3 DE 2040653 C3 DE2040653 C3 DE 2040653C3 DE 19702040653 DE19702040653 DE 19702040653 DE 2040653 A DE2040653 A DE 2040653A DE 2040653 C3 DE2040653 C3 DE 2040653C3
- Authority
- DE
- Germany
- Prior art keywords
- aldehyde
- yellow
- methylene
- dihydroindole
- trimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 53
- 238000004043 dyeing Methods 0.000 title claims description 15
- 239000000835 fiber Substances 0.000 title claims description 15
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- 229920001577 copolymer Polymers 0.000 title claims description 4
- 229920000742 Cotton Polymers 0.000 title claims description 3
- 239000010985 leather Substances 0.000 title claims description 3
- 229920005610 lignin Polymers 0.000 title claims description 3
- 229920000642 polymer Polymers 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- VXMKYRQZQXVKGB-CWWHNZPOSA-N Tannin Chemical compound O([C@H]1[C@H]([C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]([C@H]2O)O1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 VXMKYRQZQXVKGB-CWWHNZPOSA-N 0.000 title description 2
- 229920001864 tannin Polymers 0.000 title description 2
- 239000001648 tannin Substances 0.000 title description 2
- 235000018553 tannin Nutrition 0.000 title description 2
- -1 methoxy, carbomethoxy Chemical group 0.000 claims description 59
- 239000000460 chlorine Substances 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 150000001450 anions Chemical class 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000002560 nitrile group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000005425 toluyl group Chemical group 0.000 claims description 2
- FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 150000001299 aldehydes Chemical class 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 229920002239 polyacrylonitrile Polymers 0.000 description 12
- QRWRJDVVXAXGBT-UHFFFAOYSA-N 2-methyl-2,3-dihydro-1H-indole Chemical compound C1=CC=C2NC(C)CC2=C1 QRWRJDVVXAXGBT-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 229960000583 Acetic Acid Drugs 0.000 description 9
- 125000004432 carbon atoms Chemical group C* 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- FFRBMBIXVSCUFS-UHFFFAOYSA-N Martius yellow Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 8
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 8
- YMQSXQDLKTVJPD-UHFFFAOYSA-N 2,5-dichloro-5-[(1,4-dichlorocyclohexa-2,4-dien-1-yl)methoxymethyl]cyclohexa-1,3-diene Chemical compound C1=CC(Cl)=CCC1(Cl)COCC1(Cl)C=CC(Cl)=CC1 YMQSXQDLKTVJPD-UHFFFAOYSA-N 0.000 description 7
- BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- IGPFOKFDBICQMC-UHFFFAOYSA-N 3-phenylmethoxyaniline Chemical compound NC1=CC=CC(OCC=2C=CC=CC=2)=C1 IGPFOKFDBICQMC-UHFFFAOYSA-N 0.000 description 5
- FIIDVVUUWRJXLF-UHFFFAOYSA-N 4-phenylmethoxyaniline Chemical compound C1=CC(N)=CC=C1OCC1=CC=CC=C1 FIIDVVUUWRJXLF-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 230000002378 acidificating Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
- BMIPMKQAAJKBKP-UHFFFAOYSA-N 2,4,5-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C=C1C BMIPMKQAAJKBKP-UHFFFAOYSA-N 0.000 description 4
- PLPVLSBYYOWFKM-UHFFFAOYSA-N 2-phenylmethoxyaniline Chemical compound NC1=CC=CC=C1OCC1=CC=CC=C1 PLPVLSBYYOWFKM-UHFFFAOYSA-N 0.000 description 4
- QIKYZXDTTPVVAC-UHFFFAOYSA-N 4-aminobenzamide Chemical compound NC(=O)C1=CC=C(N)C=C1 QIKYZXDTTPVVAC-UHFFFAOYSA-N 0.000 description 4
- RRCAJFYQXKPXOJ-UHFFFAOYSA-N 4-aminobenzene-1,2-dicarbonitrile Chemical compound NC1=CC=C(C#N)C(C#N)=C1 RRCAJFYQXKPXOJ-UHFFFAOYSA-N 0.000 description 4
- XGQWHHCZIMXNHG-UHFFFAOYSA-N 4-aminonaphthalene-2,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 XGQWHHCZIMXNHG-UHFFFAOYSA-N 0.000 description 4
- GCWYXRHXGLFVFE-UHFFFAOYSA-N 4-hydroxy-2,6-dimethylaniline Chemical compound CC1=CC(O)=CC(C)=C1N GCWYXRHXGLFVFE-UHFFFAOYSA-N 0.000 description 4
- CYTYCFOTNPOANT-UHFFFAOYSA-N Ethylene tetrachloride Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 4
- 229940093915 Gynecological Organic acids Drugs 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- CDGNLUSBENXDGG-UHFFFAOYSA-N meta-Cresidine Chemical compound COC1=CC=C(N)C(C)=C1 CDGNLUSBENXDGG-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000011528 polyamide (building material) Substances 0.000 description 4
- 229950011008 tetrachloroethylene Drugs 0.000 description 4
- LPAGFVYQRIESJQ-UHFFFAOYSA-N 2,3-dihydro-1H-indole Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 3
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 2-ethoxyaniline Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 3
- LGDHZCLREKIGKJ-UHFFFAOYSA-N 3,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C=C1OC LGDHZCLREKIGKJ-UHFFFAOYSA-N 0.000 description 3
- XQVCBOLNTSUFGD-UHFFFAOYSA-N 3-chloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1Cl XQVCBOLNTSUFGD-UHFFFAOYSA-N 0.000 description 3
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-Chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 3
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 3
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 3
- ZMVYKWOITGSLDV-UHFFFAOYSA-N N-(4-amino-2-methoxyphenyl)acetamide Chemical compound COC1=CC(N)=CC=C1NC(C)=O ZMVYKWOITGSLDV-UHFFFAOYSA-N 0.000 description 3
- VMPITZXILSNTON-UHFFFAOYSA-N O-Anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- YTCAUTNHOOXEDG-UHFFFAOYSA-N 1,4-dimethoxycyclohexa-2,4-dien-1-amine Chemical compound COC1=CCC(N)(OC)C=C1 YTCAUTNHOOXEDG-UHFFFAOYSA-N 0.000 description 2
- FFDVTEHMPLVFMS-UHFFFAOYSA-N 2,3,5-trimethylaniline Chemical compound CC1=CC(C)=C(C)C(N)=C1 FFDVTEHMPLVFMS-UHFFFAOYSA-N 0.000 description 2
- GEQNZVKIDIPGCO-UHFFFAOYSA-N 2,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C(OC)=C1 GEQNZVKIDIPGCO-UHFFFAOYSA-N 0.000 description 2
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- DNWYJDQZZLREEU-UHFFFAOYSA-N 2-[[(2-amino-5-methylphenyl)-phenylmethoxy]-phenylmethyl]-4-methylaniline Chemical compound CC1=CC=C(N)C(C(OC(C=2C=CC=CC=2)C=2C(=CC=C(C)C=2)N)C=2C=CC=CC=2)=C1 DNWYJDQZZLREEU-UHFFFAOYSA-N 0.000 description 2
- LPCWHAUEVHHGOB-UHFFFAOYSA-N 2-[[(2-aminophenyl)-(4-chlorophenyl)methoxy]-(4-chlorophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1C(C=1C=CC(Cl)=CC=1)OC(C=1C(=CC=CC=1)N)C1=CC=C(Cl)C=C1 LPCWHAUEVHHGOB-UHFFFAOYSA-N 0.000 description 2
- WRUHXNVBIUSVFK-UHFFFAOYSA-N 2-[[(2-aminophenyl)-(4-methylphenyl)methoxy]-(4-methylphenyl)methyl]aniline Chemical compound C1=CC(C)=CC=C1C(C=1C(=CC=CC=1)N)OC(C=1C(=CC=CC=1)N)C1=CC=C(C)C=C1 WRUHXNVBIUSVFK-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- FDVITFMRUUGIBF-UHFFFAOYSA-N 2-methylidene-1,3-dihydroindole Chemical class C1=CC=C2NC(=C)CC2=C1 FDVITFMRUUGIBF-UHFFFAOYSA-N 0.000 description 2
- NMFFUUFPJJOWHK-UHFFFAOYSA-N 2-phenoxyaniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1 NMFFUUFPJJOWHK-UHFFFAOYSA-N 0.000 description 2
- FDQAQRLIKJFXOC-UHFFFAOYSA-N 3-[[(3-aminophenyl)-(4-methylphenyl)methoxy]-(4-methylphenyl)methyl]aniline Chemical compound C1=CC(C)=CC=C1C(C=1C=C(N)C=CC=1)OC(C=1C=C(N)C=CC=1)C1=CC=C(C)C=C1 FDQAQRLIKJFXOC-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- COOTUHZXYCEPGE-UHFFFAOYSA-N 4-(3-chlorophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(Cl)=C1 COOTUHZXYCEPGE-UHFFFAOYSA-N 0.000 description 2
- YTISFYMPVILQRL-UHFFFAOYSA-N 4-(4-chlorophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(Cl)C=C1 YTISFYMPVILQRL-UHFFFAOYSA-N 0.000 description 2
- VPCGOYHSWIYEMO-UHFFFAOYSA-N 4-(4-methylphenoxy)aniline Chemical compound C1=CC(C)=CC=C1OC1=CC=C(N)C=C1 VPCGOYHSWIYEMO-UHFFFAOYSA-N 0.000 description 2
- KHSKTRGLHASYOT-UHFFFAOYSA-N 4-[[(4-amino-2-methylphenyl)-(4-methylphenyl)methoxy]-(4-methylphenyl)methyl]-3-methylaniline Chemical compound C1=CC(C)=CC=C1C(C=1C(=CC(N)=CC=1)C)OC(C=1C(=CC(N)=CC=1)C)C1=CC=C(C)C=C1 KHSKTRGLHASYOT-UHFFFAOYSA-N 0.000 description 2
- DZNFZQRNNCRSAP-UHFFFAOYSA-N 4-[[(4-amino-3-methoxyphenyl)-phenylmethoxy]-phenylmethyl]-2-methoxyaniline Chemical compound C1=C(N)C(OC)=CC(C(OC(C=2C=CC=CC=2)C=2C=C(OC)C(N)=CC=2)C=2C=CC=CC=2)=C1 DZNFZQRNNCRSAP-UHFFFAOYSA-N 0.000 description 2
- OGWDLAWNVHIZHN-UHFFFAOYSA-N 4-[[(4-amino-3-methylphenyl)-phenylmethoxy]-phenylmethyl]-2-methylaniline Chemical compound C1=C(N)C(C)=CC(C(OC(C=2C=CC=CC=2)C=2C=C(C)C(N)=CC=2)C=2C=CC=CC=2)=C1 OGWDLAWNVHIZHN-UHFFFAOYSA-N 0.000 description 2
- VNMTUVJWEHOJGI-UHFFFAOYSA-N 4-[[(4-aminophenyl)-(2-chlorophenyl)methoxy]-(2-chlorophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1C(C=1C(=CC=CC=1)Cl)OC(C=1C(=CC=CC=1)Cl)C1=CC=C(N)C=C1 VNMTUVJWEHOJGI-UHFFFAOYSA-N 0.000 description 2
- FPNSJAZJCRPNFO-UHFFFAOYSA-N 4-[[(4-aminophenyl)-(4-chlorophenyl)methoxy]-(4-chlorophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1C(C=1C=CC(Cl)=CC=1)OC(C=1C=CC(Cl)=CC=1)C1=CC=C(N)C=C1 FPNSJAZJCRPNFO-UHFFFAOYSA-N 0.000 description 2
- CQMZKMDAYHQARW-UHFFFAOYSA-N 4-[[(4-aminophenyl)-(4-methylphenyl)methoxy]-(4-methylphenyl)methyl]aniline Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(N)=CC=1)OC(C=1C=CC(N)=CC=1)C1=CC=C(C)C=C1 CQMZKMDAYHQARW-UHFFFAOYSA-N 0.000 description 2
- DNXOZWOJLRRMAD-UHFFFAOYSA-N 4-amino-2,5-diethoxy-N-phenylbenzamide Chemical compound C1=C(N)C(OCC)=CC(C(=O)NC=2C=CC=CC=2)=C1OCC DNXOZWOJLRRMAD-UHFFFAOYSA-N 0.000 description 2
- JLNMBIKJQAKQBH-UHFFFAOYSA-N 4-cyclohexylaniline Chemical compound C1=CC(N)=CC=C1C1CCCCC1 JLNMBIKJQAKQBH-UHFFFAOYSA-N 0.000 description 2
- VXMYUOSDIMLATO-UHFFFAOYSA-N 4-dodecoxyaniline Chemical compound CCCCCCCCCCCCOC1=CC=C(N)C=C1 VXMYUOSDIMLATO-UHFFFAOYSA-N 0.000 description 2
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N Benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 240000007170 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N Diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N Glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N Linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- NCBZRJODKRCREW-UHFFFAOYSA-N M-Anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- GTTFJYUWPUKXJH-UHFFFAOYSA-N N-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=CC=C1 GTTFJYUWPUKXJH-UHFFFAOYSA-N 0.000 description 2
- RIYJCEHBINYMAW-UHFFFAOYSA-N N-methyl-4-[[[4-(methylamino)phenyl]-phenylmethoxy]-phenylmethyl]aniline Chemical compound C1=CC(NC)=CC=C1C(C=1C=CC=CC=1)OC(C=1C=CC(NC)=CC=1)C1=CC=CC=C1 RIYJCEHBINYMAW-UHFFFAOYSA-N 0.000 description 2
- SMUWTEASJQPLHK-UHFFFAOYSA-N NC1=C(C(=C(COCC2=C(C(=C(C=C2)N)Cl)C2=CC=CC=C2)C=C1)C1=CC=CC=C1)Cl Chemical compound NC1=C(C(=C(COCC2=C(C(=C(C=C2)N)Cl)C2=CC=CC=C2)C=C1)C1=CC=CC=C1)Cl SMUWTEASJQPLHK-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N Oleyl alcohol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M Perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N Pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N Suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N Zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N γ-lactone 4-hydroxy-butyric acid Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- CQYBNXGHMBNGCG-FXQIFTODSA-N (2S,3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-indol-1-ium-2-carboxylate Chemical compound C1CCC[C@@H]2[NH2+][C@H](C(=O)[O-])C[C@@H]21 CQYBNXGHMBNGCG-FXQIFTODSA-N 0.000 description 1
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-Dichloroethene Chemical compound ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- JVLMSZABUAXYSR-UHFFFAOYSA-N 1,3,3-trimethyl-2-methylidene-5-phenylmethoxyindole Chemical compound C=1C=C2N(C)C(=C)C(C)(C)C2=CC=1OCC1=CC=CC=C1 JVLMSZABUAXYSR-UHFFFAOYSA-N 0.000 description 1
- LRBNGGRKZWMAIY-UHFFFAOYSA-N 1,3,3-trimethyl-2-methylidene-7-(3-methylphenoxy)indole Chemical compound C=12N(C)C(=C)C(C)(C)C2=CC=CC=1OC1=CC=CC(C)=C1 LRBNGGRKZWMAIY-UHFFFAOYSA-N 0.000 description 1
- ZTUKGBOUHWYFGC-UHFFFAOYSA-N 1,3,3-trimethyl-2-methylideneindole Chemical compound C1=CC=C2N(C)C(=C)C(C)(C)C2=C1 ZTUKGBOUHWYFGC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RNGRRIYLRPECGA-UHFFFAOYSA-N 2,4-diethoxyaniline Chemical compound CCOC1=CC=C(N)C(OCC)=C1 RNGRRIYLRPECGA-UHFFFAOYSA-N 0.000 description 1
- WVWVZMNKVHNYDM-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;2-nonylphenol Chemical compound OCCOCCO.CCCCCCCCCC1=CC=CC=C1O WVWVZMNKVHNYDM-UHFFFAOYSA-N 0.000 description 1
- NISAHDHKGPWBEM-UHFFFAOYSA-N 2-(4-nonylphenoxy)acetic acid Chemical compound CCCCCCCCCC1=CC=C(OCC(O)=O)C=C1 NISAHDHKGPWBEM-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 2-Nitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-Vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- WPMWEFXCIYCJSA-UHFFFAOYSA-N 2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCO WPMWEFXCIYCJSA-UHFFFAOYSA-N 0.000 description 1
- VEHYCCADZJMWPR-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethanol;2-nonylphenol Chemical compound OCCOCCOCCOCCO.CCCCCCCCCC1=CC=CC=C1O VEHYCCADZJMWPR-UHFFFAOYSA-N 0.000 description 1
- HAWBYFATMVYBTD-UHFFFAOYSA-N 2-[[(2-amino-5-methylphenyl)-(4-chlorophenyl)methoxy]-(4-chlorophenyl)methyl]-4-methylaniline Chemical compound CC1=CC=C(N)C(C(OC(C=2C=CC(Cl)=CC=2)C=2C(=CC=C(C)C=2)N)C=2C=CC(Cl)=CC=2)=C1 HAWBYFATMVYBTD-UHFFFAOYSA-N 0.000 description 1
- MLMGJTAJUDSUKA-UHFFFAOYSA-N 2-ethenyl-1H-imidazole Chemical compound C=CC1=NC=CN1 MLMGJTAJUDSUKA-UHFFFAOYSA-N 0.000 description 1
- RAADBCJYJHQQBI-UHFFFAOYSA-N 2-sulfoterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(S(O)(=O)=O)=C1 RAADBCJYJHQQBI-UHFFFAOYSA-N 0.000 description 1
- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 description 1
- IEZYPBGGEATAMI-UHFFFAOYSA-N 3,4-di(propan-2-yloxy)aniline Chemical compound CC(C)OC1=CC=C(N)C=C1OC(C)C IEZYPBGGEATAMI-UHFFFAOYSA-N 0.000 description 1
- BOBOYOHBLRBMPK-UHFFFAOYSA-N 3,4-dimethoxyaniline;4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1.COC1=CC=C(N)C=C1OC BOBOYOHBLRBMPK-UHFFFAOYSA-N 0.000 description 1
- JSFAOCOPRGMGLZ-UHFFFAOYSA-N 3-(11-methyldodecoxy)propanoic acid Chemical compound CC(C)CCCCCCCCCCOCCC(O)=O JSFAOCOPRGMGLZ-UHFFFAOYSA-N 0.000 description 1
- DNDGRBKIVCOIJF-UHFFFAOYSA-N 3-[[(3-aminophenyl)-(2-chlorophenyl)methoxy]-(2-chlorophenyl)methyl]aniline Chemical compound NC1=CC=CC(C(OC(C=2C=C(N)C=CC=2)C=2C(=CC=CC=2)Cl)C=2C(=CC=CC=2)Cl)=C1 DNDGRBKIVCOIJF-UHFFFAOYSA-N 0.000 description 1
- ZEUFWHXTGJKXMY-UHFFFAOYSA-N 3-[[(5-amino-2-methylphenyl)-phenylmethoxy]-phenylmethyl]-4-methylaniline Chemical compound CC1=CC=C(N)C=C1C(C=1C=CC=CC=1)OC(C=1C(=CC=C(N)C=1)C)C1=CC=CC=C1 ZEUFWHXTGJKXMY-UHFFFAOYSA-N 0.000 description 1
- DMMXHSZRDIWDPZ-UHFFFAOYSA-N 3-ethyl-1,3-dimethyl-2-methylideneindole Chemical compound C1=CC=C2C(CC)(C)C(=C)N(C)C2=C1 DMMXHSZRDIWDPZ-UHFFFAOYSA-N 0.000 description 1
- KJZOZTHPUPMZKB-UHFFFAOYSA-N 3-nonoxypropanoic acid Chemical compound CCCCCCCCCOCCC(O)=O KJZOZTHPUPMZKB-UHFFFAOYSA-N 0.000 description 1
- JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 1
- GKVDUWJVFNUYAR-UHFFFAOYSA-N 4-(2-chlorophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1Cl GKVDUWJVFNUYAR-UHFFFAOYSA-N 0.000 description 1
- ASAOLTVUTGZJST-UHFFFAOYSA-N 4-(4-nitrophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 ASAOLTVUTGZJST-UHFFFAOYSA-N 0.000 description 1
- OCQVWZOMGURODT-UHFFFAOYSA-N 4-[[(4-amino-2-methoxyphenyl)-(4-methylphenyl)methoxy]-(4-methylphenyl)methyl]-3-methoxyaniline Chemical compound COC1=CC(N)=CC=C1C(C=1C=CC(C)=CC=1)OC(C=1C(=CC(N)=CC=1)OC)C1=CC=C(C)C=C1 OCQVWZOMGURODT-UHFFFAOYSA-N 0.000 description 1
- CYUFXRKITRBJIN-UHFFFAOYSA-N 4-[[(4-amino-2-methoxyphenyl)-phenylmethoxy]-phenylmethyl]-3-methoxyaniline Chemical compound COC1=CC(N)=CC=C1C(C=1C=CC=CC=1)OC(C=1C(=CC(N)=CC=1)OC)C1=CC=CC=C1 CYUFXRKITRBJIN-UHFFFAOYSA-N 0.000 description 1
- HWEGROYRPRFUFR-UHFFFAOYSA-N 4-[[(4-amino-2-methylphenyl)-phenylmethoxy]-phenylmethyl]-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C(C=1C=CC=CC=1)OC(C=1C(=CC(N)=CC=1)C)C1=CC=CC=C1 HWEGROYRPRFUFR-UHFFFAOYSA-N 0.000 description 1
- AUUYHBAPEQZDBU-UHFFFAOYSA-N 4-amino-5-methoxy-2-methyl-N-phenylbenzamide Chemical compound C1=C(N)C(OC)=CC(C(=O)NC=2C=CC=CC=2)=C1C AUUYHBAPEQZDBU-UHFFFAOYSA-N 0.000 description 1
- WDTRNCFZFQIWLM-UHFFFAOYSA-N 4-benzylaniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1 WDTRNCFZFQIWLM-UHFFFAOYSA-N 0.000 description 1
- RJWBTWIBUIGANW-UHFFFAOYSA-M 4-chlorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-M 0.000 description 1
- XWGJQNKDSHYJID-UHFFFAOYSA-N 4-decoxyaniline Chemical compound CCCCCCCCCCOC1=CC=C(N)C=C1 XWGJQNKDSHYJID-UHFFFAOYSA-N 0.000 description 1
- JFXDIXYFXDOZIT-UHFFFAOYSA-N 4-methoxy-N-methylaniline Chemical compound CNC1=CC=C(OC)C=C1 JFXDIXYFXDOZIT-UHFFFAOYSA-N 0.000 description 1
- TZWRMTAIHRIAFC-UHFFFAOYSA-N 4-methyl-3-phenylmethoxyaniline Chemical compound CC1=CC=C(N)C=C1OCC1=CC=CC=C1 TZWRMTAIHRIAFC-UHFFFAOYSA-N 0.000 description 1
- SODWJACROGQSMM-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-1-amine Chemical compound C1CCCC2=C1C=CC=C2N SODWJACROGQSMM-UHFFFAOYSA-N 0.000 description 1
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N Abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- RSWGJHLUYNHPMX-HNBVOPMISA-N Abietic acid Natural products C([C@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-HNBVOPMISA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 240000005337 Agave sisalana Species 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N Benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- RFZFFYQQRZAHIW-UHFFFAOYSA-N C=1C=C2N(C)C(=C)C(C)(C)C2=CC=1OCC1=CC=CC=C1Cl Chemical compound C=1C=C2N(C)C(=C)C(C)(C)C2=CC=1OCC1=CC=CC=C1Cl RFZFFYQQRZAHIW-UHFFFAOYSA-N 0.000 description 1
- WAMSGBMDBAERAH-UHFFFAOYSA-N CC1NC2=CC=CC=C2C1.COC1=CC=C(C=C1)N Chemical compound CC1NC2=CC=CC=C2C1.COC1=CC=C(C=C1)N WAMSGBMDBAERAH-UHFFFAOYSA-N 0.000 description 1
- RLYKFIHXSBDLEX-UHFFFAOYSA-N CC=1C(=C(C(=C2CC(NC=12)=C)C)S(=O)(=O)C)C Chemical compound CC=1C(=C(C(=C2CC(NC=12)=C)C)S(=O)(=O)C)C RLYKFIHXSBDLEX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229940089960 Chloroacetate Drugs 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N Cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- FYGDTMLNYKFZSV-MRCIVHHJSA-N Dextrin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1O[C@@H]1[C@@H](CO)OC(O[C@@H]2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-MRCIVHHJSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N Isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N Itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- AKUBZUGGSGGUEF-UHFFFAOYSA-N N,N-diethoxyaniline Chemical compound CCON(OCC)C1=CC=CC=C1 AKUBZUGGSGGUEF-UHFFFAOYSA-N 0.000 description 1
- FGOFNVXHDGQVBG-UHFFFAOYSA-N N-(2-methoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1NC(C)=O FGOFNVXHDGQVBG-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- WWBDKVZJCOGNCI-UHFFFAOYSA-N N-ethyl-4-[[[4-(ethylamino)phenyl]-phenylmethoxy]-phenylmethyl]aniline Chemical compound C1=CC(NCC)=CC=C1C(C=1C=CC=CC=1)OC(C=1C=CC(NCC)=CC=1)C1=CC=CC=C1 WWBDKVZJCOGNCI-UHFFFAOYSA-N 0.000 description 1
- HUJLUBGNPMWTSM-UHFFFAOYSA-N NC1=CC(C(COCC2C(C=C(C=C2)N)(Cl)C2=CC=CC=C2)C=C1)(C1=CC=CC=C1)Cl Chemical compound NC1=CC(C(COCC2C(C=C(C=C2)N)(Cl)C2=CC=CC=C2)C=C1)(C1=CC=CC=C1)Cl HUJLUBGNPMWTSM-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- BOWVQLFMWHZBEF-KTKRTIGZSA-N Oleoylethanolamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCCO BOWVQLFMWHZBEF-KTKRTIGZSA-N 0.000 description 1
- 229940023488 Pill Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N Pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 210000004243 Sweat Anatomy 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J Tin(IV) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N Undecylenic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N Vinyl fluoride Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- OMCMUCGWGRLCMF-UHFFFAOYSA-N [amino(diphenyl)methoxy]-diphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)OC(N)(C=1C=CC=CC=1)C1=CC=CC=C1 OMCMUCGWGRLCMF-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzyl-dodecyl-dimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-M crotonate Chemical compound C\C=C\C([O-])=O LDHQCZJRKDOVOX-NSCUHMNNSA-M 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Substances OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatoms Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M methanoate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002751 molybdenum Chemical class 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical class [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- FODHIQQNHOPUKH-UHFFFAOYSA-N tetrapropylene-Benzenesulfonic acid Chemical compound CC1CC11C2=C3S(=O)(=O)OC(C)CC3=C3C(C)CC3=C2C1C FODHIQQNHOPUKH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Description
Gegenstand der Erfindung sind neue Methinfarbstoffe der FormelThe invention relates to new methine dyes of the formula
worin R1 und R4 Tür Halogen, C1-C5-AIiCyI, Cyclohexyl, gegebenenfalls im Phenylkern durch Chlor-, Brom-, Fluor-Atome oder Äthyl-, Methyl-, Methoxy-. Carbomethoxy-, Nitro- oder Nitrilgruppen substituiertes Benzyl, ^-Phenyläthyl, Phenylpropyl(2,2), C1-C12-AJkOXy, Nitro, Cyan, Amino, Trifiuormethyl, C1 -Q-AIkoxycarbonyl, Acetyl, Propionyl,Toluyl, Benzoyl, Formylamino, Acetylamino, Propionylamino. gegebenenfalls durch Chlor oder Methyl substituiertes Benzoylamino, Carbamoyl, N-Q-Cs-Alkylcarbamoyl, N,N - Di - C1 - C5 - alkylcarbamoyl, N - C1 - C5 - Alkyl-N-phenyl- oder -naphthylcarbamoyl, das im aromatischen Ring durch Chlor-, Brom-, Fluor-Atome oder Äthyl-, Methyl-, Methoxy-, Carbomethoxy-, Nitro- oder Nitrilgruppen substituiert sein kann. Sulfamoyl N - C, - C2 - Alkylsulfamoyl. N,N - Di - C1 - C5 - alkylsulfamoyl, Q-Gi-Alkylsulfonyl. gegebenenfalls durch Chlor-, Brom-, Fluor-Atome oder Äthyl-, Methyl-, Methoxy-, Carbomethoxy-, Nitro- oder Nitrilgruppen substituiertes Phenylsulfonyl stehen und wobei mindestens einer der Substituenten R1 und R4 für Phenoxy, Naphthoxy, Benzyloxy, Phenyläthyloxy, Phenylpropyl(2,2)-oxy, Benzyloxycarbonyl, a-Phenyläthoxycarbonyl, /7-Phenyläthoxycarbonyl, -/-Phenyl-n-propoxycarbonyl, Phenoxycarbonyl oder Phenoxymethyl, die im aromatischen Ring durch Chlor-, Brom-, Fluor-Atome oder niedere Alkyl-, niedere Alkoxy-! Carbomethoxy-, Nitro-, Nitril-, Acetylamino- oder Hydroxygruppen substituiert sein können, stehen, R2 für Wasserstoff, C1 -C5-AIk)-I, Cyclohexyl, gegebenenfalls im Phenylring durch Chlor-, Brom-, Fluor-Atome oder Äthyl-, Methyl-, Methoxy-, Carbomethoxy-, Nitro- oder Nitrilgruppen substituiertes Benzyl, p-Phenyläthyl, Phenylpropyl(2,2), Phenyl oder Naphthyl, R3 Tür Wasserstoff oder C1-C5-A^yI, das zur benachbarten Stellung des Ringes B einen 5- oder 6gliedrigen N-haltigen gesättigten Ring schließen kann, der methylsubstituiert oder mit einem weiteren Cyclohexanring kondensiert sein kann, R5 und R6 Tür C1-C5-A^yI, gegebenenfalls im Phenylkern durchwherein R 1 and R 4 door halogen, C 1 -C 5 -AliCyI, cyclohexyl, optionally in the phenyl nucleus by chlorine, bromine, fluorine atoms or ethyl, methyl, methoxy. Carbomethoxy, nitro or nitrile groups substituted benzyl, ^ -phenylethyl, phenylpropyl (2.2), C 1 -C 12 -AJkOXy, nitro, cyano, amino, trifluoromethyl, C 1 -Q-alkoxycarbonyl, acetyl, propionyl, toluyl, Benzoyl, formylamino, acetylamino, propionylamino. benzoylamino, carbamoyl, NQ-Cs-alkylcarbamoyl, N, N - di - C 1 - C 5 - alkylcarbamoyl, N - C 1 - C 5 - alkyl-N-phenyl- or -naphthylcarbamoyl, which is optionally substituted by chlorine or methyl aromatic ring can be substituted by chlorine, bromine, fluorine atoms or ethyl, methyl, methoxy, carbomethoxy, nitro or nitrile groups. Sulfamoyl N - C 1 - C 2 alkylsulfamoyl. N, N - di - C 1 - C 5 - alkylsulfamoyl, Q-Gi-alkylsulfonyl. Phenylsulfonyl optionally substituted by chlorine, bromine, fluorine atoms or ethyl, methyl, methoxy, carbomethoxy, nitro or nitrile groups and where at least one of the substituents R 1 and R 4 is phenoxy, naphthoxy, benzyloxy, phenylethyloxy , Phenylpropyl (2,2) -oxy, benzyloxycarbonyl, a-phenylethoxycarbonyl, / 7-phenylethoxycarbonyl, - / - phenyl-n-propoxycarbonyl, phenoxycarbonyl or phenoxymethyl, which are in the aromatic ring by chlorine, bromine, fluorine atoms or lower Alkyl, lower alkoxy! Carbomethoxy, nitro, nitrile, acetylamino or hydroxyl groups can be substituted, R 2 stands for hydrogen, C 1 -C 5 -alk) -I, cyclohexyl, optionally in the phenyl ring by chlorine, bromine or fluorine atoms or ethyl, methyl, methoxy, carbomethoxy, nitro or nitrile groups substituted benzyl, p-phenylethyl, phenylpropyl (2,2), phenyl or naphthyl, R 3 door hydrogen or C 1 -C 5 -A ^ yI, which can close a 5- or 6-membered N-containing saturated ring to the adjacent position of ring B, which can be methyl-substituted or fused with another cyclohexane ring, R 5 and R 6 door C 1 -C 5 -A ^ yI, optionally in the phenyl nucleus through
Chlor-, Brom-, Fluor-Atome oder Äthyl-, Methyl-, Methoxy-, Carbomethoxy-, Nitro- oder Nitrilgruppen substituiertes Benzyl, ^-Phenyläthyl oder Phenylpropyl(2,2) oder Cyclohexyl, α für die Zahlen 0, 1, 2 oder 3, b für die Zahlen 0, 1, 2 oder 3 und A" für ein Anion steht, und wobei der Ring D mit einem Benzolring kondensiert sein kann.Chlorine, bromine, fluorine atoms or ethyl, methyl, methoxy, carbomethoxy, nitro or nitrile groups substituted benzyl, ^ -phenylethyl or phenylpropyl (2,2) or cyclohexyl, α for the numbers 0, 1, 2 or 3, b stands for the numbers 0, 1, 2 or 3 and A ″ stands for an anion, and ring D can be fused with a benzene ring.
Die Erfindung betrifft auch Verfahren zur Herstellung der Farbstoffe und ihre Verwendung zum Färben und Bedrucken.The invention also relates to processes for the preparation of the dyes and their use for Dyeing and printing.
Als anionische Reste A" kommen die für basische ; Farbstoffe üblichen organischen und anorganischen Anionen in Betracht, beispielsweise sind zu nennen: Chlorid, Bromid, Jodid, Carbonat, Bicarbonat, CH3SO4 , C2H5SO4", p-Toluolsulfonat, HSO4;, SO; ",Suitable anionic radicals A "for basic come; colorants customary organic and inorganic anions into consideration, for example, are: chloride, bromide, iodide, carbonate, bicarbonate, CH 3 SO 4, C 2 H 5 SO 4", p-toluenesulfonate , HSO 4 ;, SO; ",
Disulfa^Aminosulfonat.Methansulfona^Benzolsulfonat, p-Chlorbenzolsulfonat, Dihydrogenphosphat, Phosphat, Phosphormolybdat, Phosphorwolframmolybdat, Acetat, Chloracetat, Formiat, Propionat," Lactat, Crotonat, Benzoat, NO3", Perchlorat, ZnCl3",Disulfa Aminosulfonat.Methansulfona ^ ^ benzenesulfonate, p-chlorobenzenesulfonate, dihydrogen, phosphate, phosphomolybdate Phosphorwolframmolybdat, acetate, chloroacetate, formate, propionate, "lactate, crotonate, benzoate, NO 3", perchlorate, ZnCl 3 ",
die Anionen gesättigter oder ungesättigter aliphatischer Dicarbonsäuren, wie die Malonsäure, Maleinsäure, Zitronensäure, Weinsäure, Oxalsäure, Itaconsäure, Bernsteinsäure, Glutarsäure, Adipinsäure, Pimelinsäure und Suberinsäure sowie die Anionen weiterer organischer einbasischer Säuren mit 4- 30 Kohlenstoffatomen. Bevorzugt sind farblose Anionen; für das Färben aus wäßrigem Medium sind solche Anionen bevorzugt, die die Wasserlöslichkeit des Farbstoffs nicht zu stark beeinträchtigen. Für dasthe anions of saturated or unsaturated aliphatic dicarboxylic acids, such as malonic acid, maleic acid, Citric acid, tartaric acid, oxalic acid, itaconic acid, succinic acid, glutaric acid, adipic acid, pimelic acid and suberic acid and the anions of other organic monobasic acids with 4-30 carbon atoms. Colorless anions are preferred; for dyeing from an aqueous medium are those Preferred anions that do not affect the water solubility of the dye too much. For the
Färben aus organischen Lösungsmitteln sind vielfach auch solche Anionen bevorzugt, die die Löslichkeit des Farbstoffs in organischen Lösungsmitteln fördern oder zumindest nicht negativ beeinflussen.When dyeing from organic solvents, preference is also given in many cases to those anions that increase solubility promote the dye in organic solvents or at least not negatively influence it.
Eine bevorzugte Gruppe innerhalb der erfindungs-A preferred group within the invention
gemäßen Farbstoffe sind solche der allgemeinen Formel appropriate dyes are those of the general formula
CH = CH-NHCH = CH-NH
R-,R-,
(ID(ID
worin R7 für Methyl, Äthyl oder Benzyl, R8 für hexyl-, Methoxy-, Äthoxy-, Dodecyloxy-, Acetyl-wherein R 7 for methyl, ethyl or benzyl, R 8 for hexyl, methoxy, ethoxy, dodecyloxy, acetyl
gleiche oder verschiedene Methyl-, Äthyl-, tertiär- 65 amino-, Nitro-, Carbomethoxy-, Carboäthoxy-, Carb-identical or different methyl, ethyl, tertiary 65 amino, nitro, carbomethoxy, carboethoxy, carb
Butyl-, Cyclohexyl-, Hydroxy-, Methoxy-, Äthoxy-, amoyl, N-Methyl-N-phenyl-carbamoyl, N-Äthyl-Butyl, cyclohexyl, hydroxy, methoxy, ethoxy, amoyl, N-methyl-N-phenyl-carbamoyl, N-ethyl
\cetylamino-, Nitrogruppen oder Chloratome, R9 für N - phenyl - carbamoyl, Sulfamoyl-, Methylsulfonyl-,\ cetylamino, nitro or chlorine atoms, R 9 for N - phenyl - carbamoyl, sulfamoyl, methylsulfonyl,
deiche oder verschiedene Methyl-, Äthyl-, Cyclo- Phenylsulfonyl-, Cyan-, Trifluormethylgruppen,dike or various methyl, ethyl, cyclo, phenylsulfonyl, cyano, trifluoromethyl groups,
ς itpre bevorzugte Gruppe innerhalb derς itpre preferred group within the
r· A\r Zahlen Eine W "sften Farbstoffe hat die allgemeiner · A \ r numbers A W "sften dyes has the general
Chlor-, Brom- und/oder Fluoratome ,nte du^ findungsgemaßenChlorine, bromine and / or fluorine atoms , according to our finding
0,1,2 oder 3, π Tür die Zahlen 0,1,2 oder J un Formel 0,1,2 or 3, π door the numbers 0,1,2 or J in a formula
ein Anion steht.is an anion.
CH3 CH 3
/V-I-CH3 / VI-CH 3
, CH = CH-R7 , CH = CH-R 7
Eine weitere bevorzugteAnother preferred one
CH=CH-NHCH = CH-NH
worin R7, R8, R9, m, " und A" ζ^ Weiterhin bevorzugt sind Farbstoff derwherein R 7 , R 8 , R 9 , m, "and A" ζ ^ are also preferred dyes
w(i η ηw (i η η
7 87 8
Chlorsubstituenten, R11 Wasserstoff, Methyl, Äthyl, Methoxy, Athoxy oder Chlor und u dieZahlen 0,1,2 oder 3 bedeutet. ' ■Chlorine substituents, R 11 is hydrogen, methyl, ethyl, methoxy, ethoxy or chlorine and u is the numbers 0, 1, 2 or 3. '■
Von besonderer Bedeutung sind erfindungsgemäße Farbstoffe der allgemeinen FormelDyes of the general formula according to the invention are of particular importance
CH,CH,
,^^-ch^o^ >—1-™3, ^^ - ch ^ o ^> —1- ™ 3
CH=CH-NCH = CH-N
worin R7, R10, R11, u und A die oben angeführte Bedeutung haben.wherein R 7 , R 10 , R 11 , u and A are as defined above.
Eine weitere, besonders bevorzugte Gruppe innerhalb der erfindungsgemäßen Farbstoffe sind solche der allgemeinen FormelA further, particularly preferred group within the dyes according to the invention are those of the general formula
.(Ri. (Ri
CH=CH-NHCH = CH-NH
worin R7, R9, R10, R11, m, u und A die oben angeführte Bedeutung haben.wherein R 7 , R 9 , R 10 , R 11 , m, u and A have the meaning given above.
Bevorzugte erfindungsgemäße Methinfarbstoffe sind auch solche der allgemeinen FormelPreferred methine dyes according to the invention are also those of the general formula
CH = CH-NH-\ J>CH = CH-NH- \ J>
worin m, R9 und A " die obengenannte Bedeutung haben, R12 Methyl oder Äthyl, R13 Wasserstoff oder Methyl und
w die Zahlen 1, 2 oder 3 bedeutet.
Schließlich sind auch Farbstoffe der allgemeinen Formelwhere m, R 9 and A ″ have the abovementioned meaning, R 12 denotes methyl or ethyl, R 13 denotes hydrogen or methyl and w denotes the numbers 1, 2 or 3.
Finally, there are also dyes of the general formula
CH,CH,
CHJ —OOC-CHJ —OOC-
CH=CH-NCH = CH-N
■12■ 12
Pill)Pill)
worin R12, R13, A und w die genannten Bedeutung haben, bevorzugt.in which R 12 , R 13 , A and w have the meanings given, are preferred.
Besondere Bedeutung haben die erfindungsgemäßen Farbstoffe für die Färberei aus Chlorkohlenwasserstoffen, wenn das Anioo A" in den Formeln II bis XII das Anion einer einbasischen organischen Säure mil 4—30 Kohlenstoffatomen istThe dyes according to the invention are of particular importance for dyeing from chlorinated hydrocarbons, when the anion A "in formulas II to XII is the anion of a monobasic organic acid mil Is 4-30 carbon atoms
Die Farbstoffe der allgemeinen Formel (I) weiden hergestellt, indem man in an sich bekannter Weise Amine der Formel haben, mit Aldehyden der FormelThe dyes of the general formula (I) are prepared by in a manner known per se Have amines of the formula with aldehydes of the formula
R5 R 5
(XlV)(XlV)
CH- CHOCH- CHO
(XIlI)(XIlI)
6565
worin h. B, R, und Fi4 die obengenannte Bedeutung worin a, D, R1, R2, R5 und R6 die oben angegebene Bedeutung haben, oder deren funktionellen Derivaten kondensiert.where h. B, R, and Fi 4 have the abovementioned meanings in which a, D, R 1 , R 2 , R 5 and R 6 have the meanings given above, or their functional derivatives are condensed.
Die Kondensation kann derart durchgeführt werden, daß man die Lösung oder Aufschlämmung äquimolarer Mengen der Verbindungen (XIII) und Q(IV) in einer organischen oder anorganischen Säure oder deren Mischung mit Wasser bei 10—1201X, vorzugsweise bei 20 -600C verrührt. Geeignet sind beispicis-The condensation can be carried out in such a way that the solution or slurry of equimolar amounts of the compounds (XIII) and Q (IV) in an organic or inorganic acid or its mixture with water at 1 X 10-120, preferably at 20 -60 0 C. stirred. Suitable examples are
709 620/129709 620/129
20 40^5320 40 ^ 53
weise verdünnte wäßrige Mineralsäuren wie Schwefelsäure, Phosphorsäure oder Salzsäure. Weiter geeignet sind niedere Fettsäuren wie Ameisensäure, Essigsäure, Propionsäure, Buttersäure, Milchsäure und deren Mischungen mit Wasiser. 5wise dilute aqueous mineral acids such as sulfuric acid, phosphoric acid or hydrochloric acid. Further suitable are lower fatty acids such as formic acid, acetic acid, propionic acid, butyric acid, lactic acid and their Mixtures with wasiser. 5
Die Kondensation kann auch in einem Lösungsmittel wie etwa Benzol, Toluol, Chlorbenzol, Methanol und Äthanol in Gegenwart saurer Kondensationsfnittel, wie etwa Phosphoroxychlorid, Phosphorpentoxid, Zinkchlorid, Aluminiumchlorid, Zinnchlorid, ι ο Schwefelsäure, Phosphorsäure. Polyphosphorsäure oder Salzsäure oder deren Mischungen durchgeführt werden.The condensation can also take place in a solvent such as benzene, toluene, chlorobenzene, methanol and ethanol in the presence of acidic condensation agents such as phosphorus oxychloride, phosphorus pentoxide, Zinc chloride, aluminum chloride, tin chloride, ι ο sulfuric acid, phosphoric acid. Polyphosphoric acid or hydrochloric acid or mixtures thereof are carried out.
Als Aminkomponenten der FormelXlII seien z.B. genannt: 15The amine components of the formula XII include, for example: 15
4-A.minodiphenyläther, 4-Amino-4'-methyldiphenyläther. 4-A.minodiphenyl ether, 4-amino-4'-methyldiphenyl ether.
4-Amino-4'-ä'thyJdiphenyläther, 4-Amino-4'-tertiär-butyldi phenyläther, 204-Amino-4'-ethyJdiphenylether, 4-Amino-4'-tertiary-butyldi phenyl ether, 20
^Amino^'-cyclohexyldiphenyläther, 4-Amino-2'-methyldiphenyläther,
4-Amino-3'-methyldiphenyläther, 4-Amino-4'-inethoxy-diphenyläther,
^ Amino ^ '- cyclohexyldiphenyl ether, 4-amino-2'-methyldiphenyl ether,
4-amino-3'-methyldiphenyl ether, 4-amino-4'-inethoxy-diphenyl ether,
4-Amino-3'-metfaoxy-diphenyläther, 4-Amino- 25
4'-äthoxy-diphenyläther,
4-Amino-4'-4'-acetylamino-diphenyläther,
4-Amino-4'-hydroxydiphenyläther, 4-Amino-4'-mtrodiphenyläther, 4-Amino-4'-chlordiphenyIäther,
304-amino-3'-metfaoxy-diphenyl ether, 4-amino-25 4'-ethoxy-diphenyl ether,
4-Amino-4'-4'-acetylamino-diphenyl ether, 4-amino-4'-hydroxydiphenyl ether, 4-amino-4'-mtrodiphenyl ether, 4-amino-4'-chlorodiphenyl ether, 30
^Amino-^'-chlordiphenyläther, 4-Amino-3 '-chlordiphenyläther,^ Amino - ^ '- chlorodiphenyl ether, 4-amino-3 '-chlorodiphenyl ether,
4-Amino-phenyl-a-naphthyläther, 4-AminophenyI-/?-naphthyläther, 4-Amino-phenyl-a-naphthyl ether, 4-aminophenyl - /? - naphthyl ether,
4-Amino-2 ',3 ',5 '-trimethyldiphenyläther, 354-Amino-2 ', 3', 5 '-trimethyldiphenyl ether, 35
4-Aminophenylbenzyläther,
3-Aminophenylbenzyläther, 2-Amino-phenylbenzyläther,
2-Aminodiphenyläther, 4-Aminophenyl-p-methylbenzyläther, 4-Aminophenyl-p-chlorbenzyläther,
404-aminophenylbenzyl ether,
3-aminophenylbenzyl ether, 2-aminophenylbenzyl ether, 2-aminodiphenyl ether, 4-aminophenyl-p-methylbenzyl ether, 4-aminophenyl-p-chlorobenzyl ether, 40
4-Aminophenyl-o-chlorbenzyIäther, 4-Aminophenyl-m, p-dichlorbenzyläther, 4-Aminobenzyl-2',4',5'-trichlorbenzyläther, 3-Aminophenyl-p-methylbenzyläther, S-Aminophenyl-p-chlorbenzyläther, 454-aminophenyl-o-chlorobenzyl ether, 4-aminophenyl-m, p-dichlorobenzyl ether, 4-aminobenzyl-2 ', 4', 5'-trichlorobenzyl ether, 3-aminophenyl-p-methylbenzyl ether, S-aminophenyl-p-chlorobenzyl ether, 45
3-Aininopb.enyI-Q-chlorbenzyläther, 3-A minophenyl-m, p-dichlorbenzyläther, 3-Aminophenyl-2',4\5'-trichIorbenzyIäther, 2-Aminophenyl-p-methylbenzyläther, 2-Aminophenyl-p-chIorbenzyläther. 503-Aininopb.enyI-Q-chlorobenzyl ether, 3-A minophenyl-m, p-dichlorobenzyl ether, 3-aminophenyl-2 ', 4 \ 5'-trichlorobenzyl ether, 2-aminophenyl-p-methylbenzyl ether, 2-aminophenyl-p-chlorobenzyl ether. 50
2-Aminophenyl-m, p-dichlorbenzyläther, 2-Amino-2',4\5'-trichlorbenzyläther, 4-Amino-2-methyl-phenyl-benzyläther. 5-Amino-2-methyl-phenyl-benzyläther. 2-Amino-5-methyl-phenyl-benzyläther, 552-aminophenyl-m, p-dichlorobenzyl ether, 2-Amino-2 ', 4 \ 5'-trichlorobenzyl ether, 4-amino-2-methyl-phenyl-benzyl ether. 5-Amino-2-methyl-phenyl-benzyl ether. 2-Amino-5-methyl-phenyl-benzyl ether, 55
4-Amino-2-methoxy-phenyl-benzyläthcΓ, 4-Amino-3-methoxy-phenyl-benzyläther, 4-Amino-3-methyl-phenyl-benzyläther, 4-Amino-3-chIor-phenyl-benzyläther, ^Amino^-chlor-phenyl-benzyläther. 604-Amino-2-methoxy-phenyl-benzyläthcΓ, 4-amino-3-methoxy-phenyl-benzyl ether, 4-amino-3-methyl-phenyl-benzyl ether, 4-Amino-3-chloro-phenyl-benzyl ether, ^ amino ^ -chloro-phenyl-benzyl ether. 60
4-Arnino-2-methyl-phenyl-p-methylbenzyläther, 5-Amino-2-methyl-phenyl-m, p-dichlorbenzyläther, 4-amino-2-methyl-phenyl-p-methylbenzyl ether, 5-amino-2-methyl-phenyl-m, p-dichlorobenzyl ether,
2-Amino-5-methyl-phenyl-p-chlorbenzyläther, 4-Amin o-2-methoxy-phenyl-p-methylbenzyl- 652-amino-5-methyl-phenyl-p-chlorobenzyl ether, 4-amine o-2-methoxyphenyl-p-methylbenzyl-65
äther,ether,
4-Amino-3-methyl-phenyl-2',4',5'-trichlorbenzyläther, 4-Amino-3-methyl-phenyl-2 ', 4', 5'-trichlorobenzyl ether,
Anilin, p-Toluidin, m-Toluidin, o-Anisidin, ; νAniline, p-toluidine, m-toluidine, o-anisidine,; ν
m-Anisidin, p-Anisidin, ·■'.' m-anisidine, p-anisidine, · ■ '.'
o-Phenetidin, p-Phenetidin, 4-Dodecyloxyanilin;.; 4-Aminoacetanilid, N-Benzoyl-p-phenylendiamin, 2,4-Dimethoxyanilin, o-phenetidine, p-phenetidine, 4-dodecyloxyaniline;.; 4-aminoacetanilide, N-benzoyl-p-phenylenediamine, 2,4-dimethoxyaniline,
2,5-Dimethoxyanilin, 3,4-Dimethoxyanilin, 2-Chlor-4-aminoanisol, 2,4,5-Trimethylanilin, 2,3,5-Trimethylanilin, 5-Amino-2-acetylaminoanisol, 6-Amino-3-methoxy-toluol, 3,4-Dicyananilin, p-Sulfanilsäureamid, 4-Aminobenzamid, 4-Chloranilin, 4-Fluoranilin, l,2,3,4-Tetrahydro-5-amino-naphthalin, 4-Amino-2,5-diäthoxy-benzoesäureanilid, 4-Amino-2-methyl-5-methoxybenzanilid, 4-Cyclohexylanilin, 2,4-Diäthoxyanilin, 2-Aminonaphthalin, 2-Metnyl-2,3-dihydroindol,2,5-dimethoxyaniline, 3,4-dimethoxyaniline, 2-chloro-4-aminoanisole, 2,4,5-trimethylaniline, 2,3,5-trimethylaniline, 5-amino-2-acetylaminoanisole, 6-amino-3-methoxy-toluene, 3,4-dicyananiline, p-sulfanilic acid amide, 4-aminobenzamide, 4-chloroaniline, 4-fluoroaniline, l, 2,3,4-tetrahydro-5-amino-naphthalene, 4-amino-2,5-diethoxy-benzoic anilide, 4-amino-2-methyl-5-methoxybenzanilide, 4-cyclohexylaniline, 2,4-diethoxyaniline, 2-aminonaphthalene, 2-methyl-2,3-dihydroindole,
Hexahydrocarbazol, 1,2,3,4-Tetrahydrochinolin, 1,2,3,4-Tetrahydro-6-methoxychinolin, 4-Methylamino-phenylbenzyläther, 4-Äthyl-Hexahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydro-6-methoxyquinoline, 4-methylamino-phenylbenzyl ether, 4-ethyl
amino-phenylbenzyläther.amino-phenylbenzyl ether.
Als Aldehyde der FormelXIV kommen z.B. in Betracht:Aldehydes of the formula XIV include, for example Consideration:
U^-Trimethyl^-methylen^-dihydroindol-U ^ -trimethyl ^ -methylene ^ -dihydroindole-
o)-aldehyd.o) aldehyde.
U^S-Tetramethyl^-melhylen^-dihydroindol-U ^ S-Tetramethyl ^ -melhylen ^ -dihydroindole-
ω-aldehyd,ω-aldehyde,
l,3,3-Trimethyl-5-chlor-2-methylen-2,3-dihydro-1,3-trimethyl-5-chloro-2-methylene-2,3-dihydro
indol-«»-aldehyd,indole - «» - aldehyde,
l,3,3-TrimethyI-5-methoxy-2-methylen-1,3-trimethyl-5-methoxy-2-methylene
2,3-dihydroindol-fo-aldehyd,2,3-dihydroindol-fo-aldehyde,
l,3,3-Trimethyl-5-carbomethoxy-2-methylen-1,3-trimethyl-5-carbomethoxy-2-methylene
2,3-dihydroindol-r,j-aldehyd,2,3-dihydroindole-r, j-aldehyde,
l^S-Trimethyl-S-carbäthoxy^-methylen-l ^ S-trimethyl-S-carbäthoxy ^ -methylene-
2,3-dihydroindol-(.i-aldehyd,'2,3-dihydroindole - (. I-aldehyde, '
l,3,3-Trimethyl-5-cyclohexyl-2-methylen-1,3-trimethyl-5-cyclohexyl-2-methylene
2,3-dihydroindol-o)-aldehyd,2,3-dihydroindole-o) -aldehyde,
l,3,3-Trimethyl-5-benzyl-2-methylen-1,3-trimethyl-5-benzyl-2-methylene
2,3-dihydroindol-m-aldehyd,2,3-dihydroindole-m-aldehyde,
l,3,3-Trimethyl-5-nitro-2-methylen-1,3-trimethyl-5-nitro-2-methylene
2.3-dihydroindoI-<-)-aldehyd,2.3-dihydroindol - <-) - aldehyde,
1.3,3-Trimethyl-7-methyl-2-methylen-1,3,3-trimethyl-7-methyl-2-methylene
2,3-dihydroindol-oh-aldehyd,2,3-dihydroindole-oh-aldehyde,
l,3.3-Trimethyl-5-trifluormethyl-2-methylen-l, 3.3-trimethyl-5-trifluoromethyl-2-methylene
2,3-dihydroindoI-m-aldehyd,2,3-dihydroindol-m-aldehyde,
l,3.3-Trimethyl-7-methoxy-2-methylen-l, 3.3-trimethyl-7-methoxy-2-methylene
2,3-dihydroindol-ro-aldehyd.2,3-dihydroindole-ro-aldehyde.
l-ÄthyI-3,3-dimethyl-2-methylen-l-EthyI-3,3-dimethyl-2-methylene
2.3-di h ydroind ol-<»-aIdehyd,2.3-dihydroindol - <»- aldehyde,
l-Äthyl-S^i.S-trimethyl^-methylen-l-ethyl-S ^ i.S-trimethyl ^ -methylene-
2.3-dihydroindol-«)-aldehyd,2,3-dihydroindole - «) - aldehyde,
l-Äthyl-3,3-dimethyl-5-chlor-2-methylen-l-ethyl-3,3-dimethyl-5-chloro-2-methylene
2,3-dihydroindoI-f.j-aldehyd,2,3-dihydroindol-f.j-aldehyde,
l-Alhyl^^-dimethyl-S-methoxy^-mcthylcn-l-Alhyl ^^ - dimethyl-S-methoxy ^ -methylcn-
2,3-dihydroindol-M-aldehyd,2,3-dihydroindole-M-aldehyde,
l-Äthyl^S-dimethyl-S-carbometlioxy-l-ethyl ^ S-dimethyl-S-carbometlioxy-
2-methylen-2,3-dihydroindol-o)-aIdehyd,2-methylene-2,3-dihydroindole-o) -aldehyde,
l-Äthyl-S^-dimethyl-S-carbäthoxy^-methylen-l-Ethyl-S ^ -dimethyl-S-carbäthoxy ^ -methylene-
2.3-dihydroindol-f.h-aldehyd, l-Äthyl-3,3,7-trimethyl-5-cyclohexyI-2-methylen-2,3-dihydroindole-f.h-aldehyde, l-ethyl-3,3,7-trimethyl-5-cyclohexyl-2-methylene
Z3-dihydroindol-f>-aIdehyd,Z3-dihydroindole-f> -aldehyde,
l-Äthyl-3,3-dimethyl-5-ben7yl-2-mcthylcn-1-ethyl-3,3-dimethyl-5-ben7yl-2-methylcn-
2.3-dihydroindol-f.i-aldehyd,2,3-dihydroindole-f.i-aldehyde,
l-Äthyl-3,3-dlmethyl-5-nitro-2-methylcn-1-ethyl-3,3-dlmethyl-5-nitro-2-methylcn-
Z3-dihydroindol-ffl-aldehyd,Z3-dihydroindole-f fl -aldehyde,
1212th
l-Benzyl-3,3-dimethyl-2-methylen-2,3-dihydroindol-m-aldehyd, I-PhenyW^-dimethyW-methylen-2,3-dihydroindol-oj-aldehyd, !,S^-Trimethyl-S-benzyloxy^-methylen-2,3-dihydroindol-oj-aIdehyd, l-AthyW^-dimethyl-S-benzyloxy-l-methylen-2,3-dihydroindol-(u-aldehyd, l-benzyl-3,3-dimethyl-2-methylene-2,3-dihydroindole-m-aldehyde, I-PhenyW ^ -dimethyW-methylene-2,3-dihydroindol-oj-aldehyde, !, S ^ -trimethyl-S-benzyloxy ^ -methylene-2,3-dihydroindole-oj-aldehyde, l-AthyW ^ -dimethyl-S-benzyloxy-l-methylene-2,3-dihydroindole- (u-aldehyde,
2,3-dihydroindol-r.i-aldehyd.2,3-dihydroindole-r.i-aldehyde.
lAS-Trimethyl-S-carbo-y-phenylpropoxy-2-Inethylen-2,3-dihydroindoI-f«-aldehyd, IAS-trimethyl-S-carbo-y-phenylpropoxy-2-ynethylene-2,3-dihydroindoI-f «-aldehyde,
l^.B-Trimethyl-oj-benzo^-methylen-2,3-dihydroindol-a>-aldehyd, l,3,3-Trimethyl-6,7-benzo-2-methy!en-2,3,3 ',4',5 ',o'-hexahydroindol-w-aldehyd,l ^ .B-trimethyl-oj-benzo ^ -methylene-2,3-dihydroindole-a> -aldehyde, 1,3,3-trimethyl-6,7-benzo-2-methy! en-2,3,3 ', 4', 5 ', o'-hexahydroindole-w-aldehyde,
l,3,3-Trimethyl-5-fluor-2-methy]en- -1,3,3-trimethyl-5-fluoro-2-methy] en-
2,3-dihydroindol-w-aldehyd,2,3-dihydroindole-w-aldehyde,
1,3,3 -frimeth yl-S-äthoxy^-methylen-2,3-dihydroindol-oj-aldehyd, 1,3,3 -frimeth yl-S-ethoxy ^ -methylene-2,3-dihydroindol-oj-aldehyde,
2,3-dihydroindo]-fi-aldehyd, l^^-Trimethyl-o-benzyloxy^-methylen-2,3-dihydroindol-(/)-aldehyd, !^,S-Trimethyl^-benzyloxy^-methylen-2,3-dihydroindoI-cj-aldehyd, l,3,3-Trimethyl-7-chlor-2-methylen-2,3-dihydroindol-di-aldehyd, l,3,3-Trimethyl-5-(4'-methylbenzyloxy)-2-methyIen-2,3-dihydroindol-«)-aldehyd, l,3,3-Trimethyl-5-(2'-chlorbenzyloxy)-2-methyten-2,3-dihydroindoI- <>i-aldehyd, l,3,3-Trimethyl-7-(4'-chlorbenzyloxy)-2-methylen-2.3-dihydroindol-tJ)-aldehyd, 2,3-dihydroindo] -fi-aldehyde, l ^^ - trimethyl-o-benzyloxy ^ -methylene-2,3-dihydroindole - (/) - aldehyde, ! ^, S-trimethyl ^ -benzyloxy ^ -methylene-2,3-dihydroindoI-cj-aldehyde, 1,3-trimethyl-7-chloro-2-methylene-2,3-dihydroindole-di-aldehyde, 1,3-trimethyl-5- (4'-methylbenzyloxy) -2-methylene-2,3-dihydroindole - «) - aldehyde, 1,3,3-Trimethyl-5- (2'-chlorobenzyloxy) -2-methylene-2,3-dihydroindol- <> i-aldehyde, 1,3,3-trimethyl-7- (4'-chlorobenzyloxy) -2-methylene-2,3-dihydroindole-tJ) -aldehyde,
2,3-dihydroindol-c;-aldehyd,2,3-dihydroindole-c; -aldehyde,
2,3-dihydroindol-i/j-aIdehyd,2,3-dihydroindole-i / j-aldehyde,
2,3-dihydroindol-(u-aldehyd, 1,3,3-1 rimethyl-5-methylsuIfonyl-2-methylen-2,3-dihydroindol-«j-aldehyd, 2,3-dihydroindole- (u-aldehyde, 1,3,3-1 trimethyl-5-methylsulfonyl-2-methylene-2,3-dihydroindole- «j-aldehyde,
y
2-methyIen-2,3-dihydroindol-o)-aldehyd,y
2-methylene-2,3-dihydroindole-o) -aldehyde,
2-methyIen-2,3-dihydroindol-o)-aldehyd, !,S^-Trimethyl-o-methoxy-S-benzyloxy-2-methylen-2,3-dihydroindol-o)-a]dehyd, 2-methylene-2,3-dihydroindole-o) -aldehyde, !, S ^ -trimethyl-o-methoxy-S-benzyloxy-2-methylene-2,3-dihydroindole-o) -a] dehyd,
2-methylen-2,3-dihydroindol-ci)-aldehyd, l^-Trimethyl-S-roethyl-o-benzyloxy-2-methylen-2,3-dihydroindol-o)-aldehyd, l,3.3-Trimethyl-7-(4'-methylbenzyloxy)-2-methyicn-2,3-dihydroindol-f/i-aldehyd, I r3r3-Trimethyl-7-(2 -chlorbenzyloxy )-2-methylen-2,3-dihydroindol-i-)-aldehyd, l^-Trimethyl-S-benzyloxy^-methyl-2-methyIen-2,3-dihydroindol-(-)-aldehyd, l,3,3-TrimethyI-5-methy]-7-(4'-methylbenzyloxy)-2-methyIen-2,3-dihydroindo1-(-)-aldehyd, 1.3,3-Tnmethyl-5-phenoxy-2-methylen-2,3-dihydroindol-f-)-aldehyd, l,3,3-Trimethyl-7-phenoxy-2-melhylen-2,3-dihydroindol-(»-aldehyd. l,3.3-Trimethy]-5-(4'-methylphenoxy)-2-methyIen-2,3-dihydroindol-(fi-aldehyd, l,J,3-Trimethyl-5-(4'-methoxyphenoxy)-2-methylen-2,3-dihydroindol-i/)-aldehyd. l,33-Trimethyl-7-(4'-methoxyphenoxy)-2-tnethyIen-2,3-dihydroindol-fu-a1dehyd, l,3,3-Trimethyl-5-(4'-chIorphenoxy)-2-methylen-2,3-dihydroindoI-f)-aldehyd, l,3.3-TrimethyI-7-(3'-methyIphenoxy)-2-methylen-2,3-dihydroindol-f»-aIdehyd. l,3,3-Trimethyl-5-(3'-mclhoxyphenoxy)-2-methylen-2,3-dihydromdol-fu-aldehyd, l^-Trimethyl-S-n-naphthyloxy^-methylen-2,3-dihydroindol-iM-aldehyd, l,33-Tnmelhyl-5-(4'-äthyIphenoxy)-2-methyIen-2^-dihydroindol-«)-aIdehyd, l,3-3-TrimethyI-5-carbobenzoxy-2-mcthylen-2,3-dihydroindol-m-aldehyd, l,3,3-Trimethyl-5-carbo-/i-pheny]äthoxy-2-methylen-2.3-dihydroindol-M-aldehyi l^^-Trimethyl-S-carbo-fz-phenyl-alhoxy-2-methyIen-2,3-dihydroindol-f/j-a]dehyd, 2-methylene-2,3-dihydroindole-ci) -aldehyde, 1,3-trimethyl-S-roethyl-o-benzyloxy-2-methylene-2,3-dihydroindole-o) -aldehyde, 1,3,3-trimethyl-7 - (4'-methylbenzyloxy) -2-methylene-2,3-dihydroindole-f / i-aldehyde, I r 3 r 3-trimethyl-7- (2-chlorobenzyloxy) -2-methylene-2,3-dihydroindole- i -) - aldehyde, l ^ -trimethyl-S-benzyloxy ^ -methyl-2-methylene-2,3-dihydroindole - (-) - aldehyde, 1,3,3-trimethyl-5-methy] -7- ( 4'-methylbenzyloxy) -2-methylene-2,3-dihydroindo1 - (-) - aldehyde, 1,3,3-methyl-5-phenoxy-2-methylene-2,3-dihydroindole-f -) - aldehyde, 3,3-trimethyl-7-phenoxy-2-methylene-2,3-dihydroindole - (»- aldehyde. 1,3,3-trimethy] -5- (4'-methylphenoxy) -2-methylene-2,3-dihydroindole - (fi-aldehyde, l, J, 3-trimethyl-5- (4'-methoxyphenoxy) -2-methylene-2,3-dihydroindol-i /) - aldehyde. 1,33-trimethyl-7- (4 ' -methoxyphenoxy) -2-methylene-2,3-dihydroindole-fu-aldehyde, 1,3,3-trimethyl-5- (4'-chlorophenoxy) -2-methylene-2,3-dihydroindole-f) -aldehyde, 1,3,3-Trimethyl-7- (3'-methylphenoxy) -2-methylene-2,3-dihydroindole-f »-aldehyde. 1,3,3-Trimethyl-5- (3'-mclhoxyphenoxy) -2-methylene-2,3-dihydromdol-fu-aldehyde, 1,4-trimethyl-Sn-naphthyloxy-3-methylene-2,3-dihydroindole-iM -aldehyde, 1,33-tri-methyl-5- (4'-ethyIphenoxy) -2-methyIen-2 ^ -dihydroindole - «) - aldehyde, l, 3-3-trimethyl-5-carbobenzoxy-2-methylene-2, 3-dihydroindole-m-aldehyde, l, 3,3-trimethyl-5-carbo- / i-pheny] ethoxy-2-methylene-2,3-dihydroindole-M-aldehyde l ^^ - trimethyl-S-carbo-fz- phenyl-alhoxy-2-methylene-2,3-dihydroindole-f / ja] dehyd,
2,3-dihydroindol-oj-aldehyd, l,3-Dimethyl-3-äthyl-2-methylen-2,3-dihydroindol-«j-aldehyd, l,3,3-Trimethy]-5-sulfonamido-2-methylen-2,3-dihydroindo]-(D-aldehyd, !,S^-Trimethyl-S-carbonamido^-methylen-2,3-dihydroindol-tu-aldehyd, !,S^-Tnmethyl-S-carbonsäure-N-äthylanilid-2-methylen-2,3-dihydroindol-c»-aldehyd. 2,3-dihydroindole-oj-aldehyde, 1,3-Dimethyl-3-ethyl-2-methylene-2,3-dihydroindole- «j-aldehyde, 1,3,3-Trimethy] -5-sulfonamido-2-methylene-2,3-dihydroindo] - (D-aldehyde, !, S ^ -trimethyl-S-carbonamido ^ -methylene-2,3-dihydroindol-tu-aldehyde, !, S ^ -Tnmethyl-S-carboxylic acid-N-ethylanilide-2-methylene-2,3-dihydroindole-C »-aldehyde.
l,3,3-Trimethyl-7-äthyl-2-methylen-2,3-dihydroindol-o)-aldehyd, 1,3,3-1 Γimethyl-5-chlor-7-methoxy-2-Iπethylen-2,3-dihydroindol-(»-aldehyd, l,3,3-TΓimethyl-4-chlor-7-methoxy-2-methylen-2,3-dihydroindol-iu-aldehyd, l^J-Trimethyl^o-dicarbomethoxy^-methylen-2,3-dihydro'.ndol-o)-aldehyd, 1.3,3-Trimethyl-4.5-dichlor-7-inethoxy-2-methylen-2,3-dihydroindol-m-aIdehyd, 1,3-trimethyl-7-ethyl-2-methylene-2,3-dihydroindole-o) -aldehyde, 1,3,3-1 Γimethyl-5-chloro-7-methoxy-2-ethylene-2,3-dihydroindole - (»- aldehyde, l, 3,3-TΓimethyl-4-chloro-7-methoxy-2-methylene-2,3-dihydroindol-iu-aldehyde, l ^ J-trimethyl ^ o-dicarbomethoxy ^ -methylene-2,3-dihydro'.ndol-o) -aldehyde, 1,3,3-trimethyl-4,5-dichloro-7-ynethoxy-2-methylene-2,3-dihydroindole-m-aldehyde,
2-methylen-2.3-dihydroindoI-oj-aldehyd,2-methylene-2,3-dihydroindol-oj-aldehyde,
2,3-dihydroindol-oj-aldehyd, l,3,3,4.6,7-Hexamethyl-2-methyIen-2,3-dihydroindol-iD-aldehyd. 2,3-dihydroindole-oj-aldehyde, 1,3,4,6,7-hexamethyl-2-methylene-2,3-dihydroindole-iD-aldehyde.
Eine andere Methode zur Darstellung der Methinfarbstoffe der Formel I beruht auf der Kondensation von N-Formylverbindungen der FormelAnother method of representing the methine dyes of the formula I is based on the condensation of N-formyl compounds of the formula
OHC-NOHC-N
worin fo, B, R3 und R4 die oben angegebene Bedeutung haben mit Dihydroindolen der Formelin which fo, B, R 3 and R 4 have the meaning given above with dihydroindoles of the formula
(XVI)(XVI)
worin o, D, Rj, R2, R5 und R6 die oben angegebene Bedeutung besitzen.wherein o, D, Rj, R 2 , R 5 and R 6 have the meanings given above.
Man arbeitet beispielsweise so, daß ein Amin der oben angeführten Formel XIII und Ameisensäure in einem inerten Lösungsmittel, etwa ChlorbenzolOne works, for example, that an amine of the above formula XIII and formic acid in an inert solvent such as chlorobenzene
erwärmt wird,' bis das gebildete Wasser azeotrop ■abgetrennt ist. Dabei arbeitet man bei der Destilla-■tionstempefatür des inerten Lösungsmittels, beispiels-■ weise bei 100—1400C.is heated until the water formed is separated azeotropically. Here, in the distillation ■ you work tionstempefatür the inert solvent, ■ beispiels-, at 100-140 0 C.
Die erhaltene Lösung der Verbindung der Formel XV versetzt man mit der äquivalenten Menge der Methylenbäse XVl. Dann setzt man bei Raumtemperatur ein saures Rondensationsmittel zu und führt die Kondensation bei Temperaturen von 20 bis 70T aus. Geeignete Kondensationsmittel sind z.B. Phosphoroxychlorid, Phosphorpentoxid. Polyphosphorsäure. Schwefelsäure. Für diese Reaktion geeignete Amine sind beispielsweise die oben angeführten Beispiele zu FormelXlIl. Hierzu geeignete 2.3-Dihydro-2-methylenindole der Formel XVl wurden bereits oben in Form ihrer (»-Aldehyde der Formel XlV aufgezählt.The resulting solution of the compound of the formula XV is mixed with the equivalent amount the methylene base XVl. An acidic condensation agent is then added at room temperature and carries out the condensation at temperatures from 20 to 70T. Suitable condensing agents are e.g. Phosphorus oxychloride, phosphorus pentoxide. Polyphosphoric acid. Sulfuric acid. Suitable for this reaction Amines are, for example, the examples given above for Formula XIII. Suitable 2,3-dihydro-2-methylene indoles for this purpose of the formula XVl have already been mentioned above in the form of their (»-aldehydes of the formula XlV enumerated.
Die neuen Produkte sind wertvolle Farbstoffe, die zum Färben und Bedrucken von Materialien aus Leder, tannierter Baumwolle, Cellulose, synthetischen Superpolyamiden und Superpolyurethanen sowie zum Färben ligninhaltiger Fasern wie Kokos, Jute und Sisal verwendet werden können. Sie sind weiter geeignet zur Herstellung von Schreibflüssigkeiten, Stempelfarben. Kugelschreiberpasten und lassen sich auch im Gummidruck verwenden.The new products are valuable dyes that for dyeing and printing materials made of leather, tanned cotton, cellulose, synthetic Super polyamides and super polyurethanes as well as for dyeing lignin-containing fibers such as coconut, jute and Sisal can be used. They are also suitable for the production of writing fluids, Stamp inks. Ballpoint pen pastes and can also be used in rubber printing.
Zum Färben mit den basischen Farbstoffen der obigen allgemeinen Formel eignen sich insbesondere Flocken, Fasern, Fäden. Bänder, Gewebe oder Gewirke aus Polyacrylnitril oder aus Mischpolymerisaten des Acrylnitrils mit anderen Vinylverbindungen wie Vinylchlorid. Vinylidenchlorid. Vinylfluorid, Vinylacetat. Vinylpyridin, Vinylimidazol, Vinylalkohol, Acryl- und Methacrylsäurecslern und -amiden, as. Dicyanäthylen. oder Flocken, Fasern. Fäden, Bänder. Gewebe oder Gewirke aus sauer modifizierten aromatischen Polyestern, sowie sauer modifizierten Polyamidfasern. Sauer modifizierte aromatische Polyester sind beispielsweise Polykondensationsprodukte aus Sulfoterephthalsäure und Äthylenglykol. d. h. sulfonsäuregruppenhaltigen Polyäthylenglykolterephthalaten (Typ DACRON 64 der E. I. DuPont de Nemours and Company), wie sie in der belgischen Patentschrift 5 49 179 und der USA.-Patentschrift 28 93 816 beschrieben sind.The basic dyes of the above general formula are particularly suitable for dyeing Flakes, fibers, threads. Tapes, woven or knitted fabrics made from polyacrylonitrile or from copolymers of acrylonitrile with other vinyl compounds such as vinyl chloride. Vinylidene chloride. Vinyl fluoride, Vinyl acetate. Vinyl pyridine, vinyl imidazole, vinyl alcohol, acrylic and methacrylic acid acids and amides, as. Dicyanethylene. or flakes, fibers. Threads, ribbons. Acid modified woven or knitted fabrics aromatic polyesters and acid-modified polyamide fibers. Acid modified aromatic polyesters are, for example, polycondensation products from sulfoterephthalic acid and ethylene glycol. d. H. Polyethylene glycol terephthalates containing sulfonic acid groups (type DACRON 64 from E. I. DuPont de Nemours and Company) as described in Belgian patent 5 49 179 and USA patent 28 93 816 are described.
Das Färben kann aus schwach saurer Flotte erfolgen, wobei man in das Färbebad zweckmäßigerweise bei 4& -600C eingeht und dann bei Kochtemperatur färbt. Man kann auch unter Dmck bei Temperaturen über 100" C färben. Des weiteren lassen sich die Farbstoffe Spinnlösungen zur Herstellung polyacrylnitrilhaltiger Fasern zusetzen oder auch auf die unverstreckte Faser aufbringen. Die Färbungen auf Polyacrylnitril, sauer modifizierten Polyestern und sauer modifiziertem Polyamid zeichnen sich durch sehr gute Licht-, Naß-, Reib- und Sublimierechtheit und durch eine hohe Affinität zur Faser aus. Die Farbstoffe bilden mit anionischen Fällungsmitteln wie Tonerde. Tannin, Phosphorwolfram-(molybdän)-säuren lichtechte Pigmente, die vorteilhaft im Papierdruck eingesetzt werden können.The dyeing may be carried out slightly acidic liquor, wherein it is advantageous to enter into the dyeing bath at 4 0 -60 C, and dyeing is then at boiling temperature. One can also dye under pressure at temperatures above 100 ° C. Furthermore, the dyes can be added to spinning solutions for the production of polyacrylonitrile-containing fibers or applied to the undrawn fibers. The dyeings on polyacrylonitrile, acid-modified polyesters and acid-modified polyamide are very good Light, wet, rubbing and sublimation fastness and a high affinity to the fiber. The dyes form lightfast pigments with anionic precipitants such as alumina, tannin, phosphotungstic (molybdenum) acids, which can be used advantageously in paper printing.
Methinfarbstoffe, deren Ringe B und D der Farbstoffe der Formel I durch Alkoxy- oder Alkoxycarbonyl-Gruppcn substituiert sind, sind bereits aus der DT-AS 1045 360. der DT-OS 19 34152 und der US-PS 31 13 825 bekannt. Gegenüber nächslvcrglcichbaren Farbstoffen dieser Literatur zeichnen sich die Farbstoffe durch eine überraschend gute Schweißechtheit aus. Beispielsweise ist in dem nach DIN 54 020 durchgeführten Schweißechtheitstest der 4. Farbstoff der Spalten 5/6 der genannten Auslegeschrifl dem neuen Farbstoff mit einer Benzylesleranstelle der Methylester-Gruppe unterlegen, und der letzte Farbstoff von Seite 4 der genannten Offenlegungsschrift und der Farbstoff von Beispiel 1 der genannten Patentschrift dem neuen Farbstoff mit einer p-Phenoxy-Gruppe anstelle der Methoxy-Gruppe(n)Methine dyes, their rings B and D of the dyes of formula I by alkoxy or alkoxycarbonyl groups are substituted, are already from the DT-AS 1045 360th the DT-OS 19 34152 and the US-PS 31 13 825 known. Compared to the next comparable The dyes in this literature are surprisingly good Perspiration fastness. For example, in the sweat fastness test carried out in accordance with DIN 54 020, the 4. Dye in columns 5/6 of the above-mentioned Auslegeschrifl the new dye with a benzyl chloride instead inferior to the methyl ester group, and the last dye from page 4 of the aforementioned Offenlegungsschrift and the dye of Example 1 of said patent, the new dye with a p-phenoxy group instead of methoxy group (s)
ίο unterlegen.ίο inferior.
Die Farbstoffe können einzeln oder in Mischungen angewendet werden.The dyes can be used individually or in mixtures be applied.
Die erfindungsgemäßen Farbstoffe sind gut zum Färben von Formkörpern aus Polymerisaten oder Mischpolymerisaten des Acrylnitrils, asymmetrischen Dicyanäthylens. sauer modifizierter aromatischer Polyester oder sauer modifizierter synthetischer Super polyamide in Chlorkohlenwasserstoffen als Färbebad geeignet, wenn sie die Löslichkeit in Chlorkohlen-Wasserstoffen fördernde Substituenten, wie z. B. die tertiär-Butylgruppe oder langkettige Alkoxygruppen wie z. B. die Dodecylgruppe tragen, oder wenn das Anion A" in den Formeln I bis XlI das Anion einer einbasischen organischen Säure mit 4— 30 Kohlenstoffatomen ist. Derartige organische Säuren sind beispielsweise: 2-Äthylcapronsäure, Laurinsäure, ölsäure. Linolsäure, ein Gemisch aliphatischer Carbonsäure mit 15—19 Kohlenstoffatomen (Versatic-Säure 1519 der Firma Shell), ein Gemisch aliphatischer Carbonsäuren mit 9—11 Kohlenstoffatomen (Versaticsäuren 911 der Firma Shell), Kokosfettsäurevorlauf, Tetradecansäure. Undecylensäure, Dimethylpropansäure, Dimethylessigsäure, Carbonsäuren, deren Kohlenstoffkette durch Heteroatome unterbrochen ist.The dyes according to the invention are good for dyeing moldings made from polymers or Copolymers of acrylonitrile, asymmetric dicyanethylene. acidic modified aromatic Polyester or acid modified synthetic super polyamides in chlorinated hydrocarbons as a dye bath suitable if they promote the solubility in chlorinated hydrocarbons substituents such. B. the tertiary butyl group or long-chain alkoxy groups such as. B. carry the dodecyl group, or if that Anion A "in formulas I to XlI is the anion of a monobasic organic acid with 4-30 carbon atoms is. Such organic acids are for example: 2-ethylcaproic acid, lauric acid, oleic acid. Linoleic acid, a mixture of aliphatic carboxylic acids with 15-19 carbon atoms (Versatic acid 1519 from Shell), a mixture of aliphatic carboxylic acids with 9-11 carbon atoms (Versatic acids 911 from Shell), coconut fatty acid forerun, tetradecanoic acid. Undecylenic acid, dimethylpropanoic acid, Dimethyl acetic acid, carboxylic acids whose carbon chain is interrupted by heteroatoms.
wie Nonylphenoltetraäthylenglykolätherpropionsäure, Nonylphenoldiäthylenglykolätherpropionsäure, Dodecyltetraäthylengiykolätherpropionsäure, 3-(Nonyloxy) - propionsäure, 3 - (Isotridecyloxy) - propionsäure, 3 - (Isotridecyloxy) - diäthylenglykolätherpro-such as nonylphenol tetraethylene glycol ether propionic acid, nonylphenol diethylene glycol ether propionic acid, Dodecyl tetraethylene glycol ether propionic acid, 3- (nonyloxy) - propionic acid, 3 - (isotridecyloxy) - propionic acid, 3 - (isotridecyloxy) - diethylene glycol ether prop-
pionsäure. Ätherpropionsäure des Alkoholgemisches mit 6—10 Kohlenstoffatomen, Nonylphenoxyessigsäure, aromatische Carbonsäuren wie tert.-Butylbenzoesäure, cycloaliphatische Carbonsäuren, wie HexahydrobenzoesäureCyclohexencarbonsäureAbietinsäure und Sulfonsäuren, wie Tetrapropylenbenzolsulfonsäure. pionic acid. Ether propionic acid of the alcohol mixture with 6-10 carbon atoms, nonylphenoxyacetic acid, aromatic carboxylic acids such as tert-butylbenzoic acid, cycloaliphatic carboxylic acids such as Hexahydrobenzoic acid cyclohexenecarboxylic acid abietic acid and sulfonic acids such as tetrapropylene benzene sulfonic acid.
Stabile konzentrierte Lösungen dieser Farbstoffe in Chlorkohlenwasserstoffen lassen sich insbesondere dann herstellen, gegebenenfalls unter Zusatz von polaren organischen Lösungsmitteln, die mit Chlorkohlenwasserstoffen vollständig mischbar sind, wie Butyrolacton, Dimethylformamid, Methanol, Dioxan, Acetonitril. Methyläthylketon, Nitrobenzol, Dimethylsulfoxid. Benzonitril und 2-Nitrochlorbenzol, wenn die erfindungsgemäßen Farbstoffe als Salze der genannten einbasischen organischen Säuren mit 4 bis 30 Kohlenstoffatomen vorliegen.Stable concentrated solutions of these dyes in chlorinated hydrocarbons can be used in particular then produce, optionally with the addition of polar organic solvents with chlorinated hydrocarbons are completely miscible, such as butyrolactone, dimethylformamide, methanol, dioxane, Acetonitrile. Methyl ethyl ketone, nitrobenzene, dimethyl sulfoxide. Benzonitrile and 2-nitrochlorobenzene if the dyes according to the invention as salts of the monobasic organic acids mentioned with 4 to 30 carbon atoms are present.
Zur Herstellung derartiger Lösungen verrührt man die erfindungsgemäßen Methinfarbstoffe (in Form der freien Basen oder als Salze von organischen Säuren mit 4—30 Kohlenstoffatomen) mit Chlorkohlenwasserstoffen und einbasischen organischen Säuren mit 4—30 Kohlenstoffatomen, gegebenenfalls unter Zusatz von polaren organischen Lösungsmitteln, die mit Chlorkohlenwasserstoffen vollständig mischbar sind, gegebenenfalls bei erhöhter Temperatur.To prepare such solutions, the methine dyes according to the invention (in the form of free bases or as salts of organic acids with 4-30 carbon atoms) with chlorinated hydrocarbons and monobasic organic acids having 4-30 carbon atoms, optionally with the addition of polar organic solvents that are completely miscible with chlorinated hydrocarbons are, optionally at elevated temperature.
In den Beispielen verhalten sich Gewichts- und Volumteile zueinander wie Gramm zu Milliliter.In the examples, parts by weight and parts by volume are related to one another as grams to milliliters.
1515th
29,3 Gewichtsteile 1,3,3 - Trimethyl - 7 - phenoxy-Z - methylen - 2,3 - dihydroindol - m - aldehyd und 13,3 Gewichtsteile 2-Methyl-2,3-dihydroindol werden mit 60 VoI am teilen Eisessig und 15 Volumteilen Wasser 4 Stunden bei Raumtemperatur verrührt, dann mit29.3 parts by weight of 1,3,3-trimethyl-7-phenoxy-Z-methylene-2,3-dihydroindole- m -aldehyde and 13.3 parts by weight of 2-methyl-2,3-dihydroindole are 60 parts by volume of glacial acetic acid and 15 parts by volume of water for 4 hours at room temperature, then stirred with
Er hat die Formel 1000 Volumteilen Wasser verdünnt. Der erhaltene Farbstoff wird mit 50 Gewichtsteilen Siedeiialz ausgesalzen, von der Lösung abgetrennt, aus 1500 Volumteilen Wasser umgelöst, wieder mit Siedeiialz ausgesalzen, abgetrennt und getrocknet.He diluted the formula 1000 parts by volume of water. The dye obtained is salted out with 50 parts by weight of Siedeiialz, separated from the solution, from 1500 parts by volume Redissolved water, salted out again with Siedeiialz, separated and dried.
CH3 // χ CH 3 // χ
CH = CH-NCH = CH-N
Cl"Cl "
und färbt Materialien aus Polyacrylnitril, sauer modi- In analoger Wehe werden bei Verwendung derand colors materials made of polyacrylonitrile, acidic modi- In analogous woes are used when using the
fizierten Polyestern und sauer modifiziertem Poly- folgenden Aldehyde und Amine ähnliche, wertvolleFied polyesters and acid modified poly- following aldehydes and amines are valuable
amid in grünstichiggelben Tönen von sehr guten 25 Farbstoffe erhalten, die Materialien aus Polyacryl-amide in greenish yellow tones obtained from very good 25 dyes, the materials made of polyacrylic
Licht- und Naßechtheiten. nitril in den angegebenen Farbtönen färben.Light and wet fastness. Color nitrile in the specified shades.
Aldehydaldehyde
indol-cu-aklehydindole-cu-aklehyd
l,3,3-Trimethyl-5-methyI-2-methylen-2,3-dihydroindol-io-aldehyd I,3,3-Trimethyl-5-methoxy-2-methylen-2,3-dihydroindol-oj-aldehyd 1,3,3-Trimethyl-5-methyl-2-methylene-2,3-dihydroindole-io-aldehyde 1,3-trimethyl-5-methoxy-2-methylene-2,3-dihydroindole-oj-aldehyde
2-methyleri-2,3-dihydroindol-cu-aldehyd l,3,3-TrimcthyI-5-carbäthoxy-2-methylen 2,3-dihydroindol-cu-aldehyd ,S^yyy 2,3-dihydroindol-to-aldehyd l,3<3-Trimethyl-5-benzyI-2-methylen-2,3-dihydroindol-aj-aldehyd l,3,3-Trimethyl-5-nitro-2-methylen-2,3 dihydroindol-oj-aldehyd l,3,3-Trimethyl-7-methyl-2-methylen-2,3-dihydroindol-f/)-aldehyd 2-methyleri-2,3-dihydroindole-cu-aldehyde 1,3-trimethyl-5-carbethoxy-2-methylene 2,3-dihydroindole-cu-aldehyde , S ^ yyy 2,3-dihydroindol-to-aldehyde 1.3 <3-trimethyl-5-benzyI-2-methylene-2,3-dihydroindole-aj-aldehyde 1,3,3-Trimethyl-5-nitro-2-methylene-2,3-dihydroindole-oj-aldehyde 1,3,3-Trimethyl-7-methyl-2-methylene-2,3-dihydroindole-f /) aldehyde
yy 2-methylen-2,3-dihydroindol-o)-aldehydyy 2-methylene-2,3-dihydroindole-o) -aldehyde
2,3-dihydroindol-o)-aldehyd l,3.3-Trirnethyl-7-chlor-2-methylen-2,3-dihydroindol-w-aldehyd 2,3-dihydroindole-o) -aldehyde 1,3,3-trimethyl-7-chloro-2-methylene-2,3-dihydroindole-w-aldehyde
2,3-dihydroindol-ω-a!dehyd l-Äthyl-3,3-dimethyl-2-methylen-2,3-dihydroindol-o)-aldehyd l-Äthyl-3,3-dimethyl-5-methyl-2-methylen 2,3-dihydroindol-oj-aldehyd2,3-dihydroindole-ω-α-dehyd 1-ethyl-3,3-dimethyl-2-methylene-2,3-dihydroindole-o) -aldehyde 1-ethyl-3,3-dimethyl-5-methyl-2-methylene 2,3-dihydroindole-oj-aldehyde
2,3-dihydroindol-iii-aldehyd 1 -Äthyl^S-dimelhyl-S-methoxy-2-methylein-2,3-dihydroindol-i')-aldehyd 2,3-dihydroindole-iii-aldehyde 1-Ethyl ^ S-dimethyl-S-methoxy-2-methylen-2,3-dihydroindole-i ') aldehyde
1717th /ο/ ο
1818th
Fortsetzungcontinuation
Aldehydaldehyde
1 -Äthyl-S^-dimethyl-S-carbathoxy-2-methyIen-2,3-dihydroindoJ-iu-aldehyd l-Äthyl-S^-dimethyl-S-cyclohexyl-2-methylen-2,3-dihydroindol-(o-aldehyd l-Äthyl-3,3-dimetb.yl-5-benzyl-2-methylen-2,3-dihydroindol-cu-aldehyd l-Äthyl-3,3-dimethyl-5-nitro-2-methylen-2,3-dihydroindol-o)-aldehyd 1,3,3 -Trimethyl^-benzyW-methy len-2,3-dihydroindol-cu-aldehyd Gemisch von:1-Ethyl-S ^ -dimethyl-S-carbathoxy-2-methylene-2,3-dihydroindoJ-iu-aldehyde 1-ethyl-S ^ -dimethyl-S-cyclohexyl-2-methylene-2,3-dihydroindole- (o-aldehyde 1-ethyl-3,3-dimetb.yl-5-benzyl-2-methylene-2,3-dihydroindole-cu-aldehyde 1-ethyl-3,3-dimethyl-5-nitro-2-methylene-2,3-dihydroindole-o) -aldehyde 1,3,3 -Trimethyl ^ -benzyW-methylene-2,3-dihydroindole-cu-aldehyde Mixture of:
l,3,3-Trimet:hyl-4-methyl-2-methylen-2,3-dihydroindoJ-/u-aJdehyd 1,3,3-Trimet: hyl-4-methyl-2-methylene-2,3-dihydroindo / u-aldehyde
l,3,3-Trimethyl-6-methyl-2-methylen-2,3-dihydroindol-tD-aldehyd l^^-Trimethyl-oJ-benzo^-methylen-2,3,3 ',4',5 \6'-hexahydroindol-a>-aldehyd 1,3,3-Trimethyl· 5-fluor-2-methylen-2,3-dihydroindol-w-aldehyd 1,3,3-Trimethyl-6-methyl-2-methylene-2,3-dihydroindole-tD-aldehyde l ^^ - trimethyl-oJ-benzo ^ -methylene-2,3,3 ', 4', 5 \ 6'-hexahydroindole-a> -aldehyde 1,3,3-trimethyl.5-fluoro-2-methylene-2,3-dihydroindole-w-aldehyde
2,3-dihydroindoI-cü-aldehyd l,3,3-Trimethyl-7-äthoxy-2-raethylen-2,3-dihydroindol- <o-aldehyd l,3,3-Trimethyl-5-cyan-2-methyIen-2,3-dihydroindol-tu-aldehyd U.S-Trimethyl-S-acetylamino^-methylen-2,3-dihydroindol-fu-aldehyd l^J-Trimethyl-S-methylsulfonyl-2-methylen-2,3-dihydΓoindol-ω-aldehyd 2,3-dihydroindol-cu-aldehyde 1,3,3-Trimethyl-7-ethoxy-2-raethylene-2,3-dihydroindole- <o-aldehyde 1,3,3-Trimethyl-5-cyano-2-methylene-2,3-dihydroindole-tu-aldehyde U.S-Trimethyl-S-acetylamino ^ -methylene-2,3-dihydroindole-fu-aldehyde l ^ J-Trimethyl-S-methylsulfonyl-2-methylene-2,3-dihydΓoindole-ω-aldehyde
ypy 2-methy!en-2,3-dihydroindol-(u-aldehydypy 2-methylene-2,3-dihydroindole- (u-aldehyde
2,3-dihydroindcl-w-aldehyd U^-Trimethyl-oJ-benzo^i-methylen-2,3-dihydroindol-iu-aldehyd lJJ-Trimethyl-S-sulfbnamido^-methylen-2,3-dihydroindol-cu-aldehyd l,3.3-Trimethyl-5-caΓbonamido-2-metl^ylen-2,3-dihydroindol-<«-aldehyd U^-Trimethyl-S-carbonsäureäthylanilid-2-methylen-2,3-dihydroindol-(u-aldehyd l,3,3,-Trimethyl-7-äthyl-2-methylen-2,3-dihydroindol-ü)-aldehyd 1 ^,S-Trimethyl-S-chlor-T-methoxy-2-methylen-2,3-dihydroindol-oj-aldehyd 1,3,3-7 rimethyl^-chlor-T-methoxy-2-methylen-2,3-dihydroindol-ri)-aldehyd 2,3-dihydroindol-w-aldehyde U ^ -trimethyl-oJ-benzo ^ i-methylene-2,3-dihydroindol-iu-aldehyde lJJ-Trimethyl-S-sulfbnamido ^ -methylene-2,3-dihydroindole-cu-aldehyde 1,3,3-Trimethyl-5-caΓbonamido-2-methylene-2,3-dihydroindole - <«- aldehyde U ^ -trimethyl-S-carboxylic acid ethylanilide-2-methylene-2,3-dihydroindole- (u-aldehyde l, 3,3, -trimethyl-7-ethyl-2-methylene-2,3-dihydroindole-ü) -aldehyde 1 ^, S-trimethyl-S-chloro-T-methoxy-2-methylene-2,3- dihydroindole-oj-aldehyde 1,3,3-7 rimethyl ^ -chloro-T-methoxy-2-methylene-2,3-dihydroindole-ri) -aldehyde
2-methylen-2,3-dihydroindol-w-aldehyd !^,S-Trimethyl-S-chloMJ-dimethoxy-2-methylen-2,3-dihydroindol-o)-aldehyd 2-methylene-2,3-dihydroindole-w-aldehyde! ^, S-trimethyl-S-chloMJ-dimethoxy-2-methylene-2,3-dihydroindole-o) -aldehyde
y^y 2-methylen-2,3-dihydΓoindol-ω-aldehyd 1,3,3,4,5,7-Hexamethyl-2-methylen-2,3-dihydroindol-cu-aldehyd l,3,3,4.,6,7-Hexamethyl-2-mcthylen-2,3-dihydroindol-ω-aldehyd Amin 4-Amino-phcnyl-benzyläther desgl. desgl. desgl. desgl.y ^ y 2-methylene-2,3-dihydΓoindole-ω-aldehyde 1,3,3,4,5,7-hexamethyl-2-methylene-2,3-dihydroindole-cu-aldehyde l, 3,3,4., 6,7-hexamethyl-2-methylene-2,3-dihydroindole-ω-aldehyde Amine 4-amino-phenyl-benzyl ether like. like. like. like.
desgl.the same
desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl.like. like. like. like. like. like. like. like. like. like. like. like. like. like. like. like. like. like. like.
Farbtonhue
grünsticliiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
rotstichiggelbreddish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
rotstichiggelbreddish yellow
grünstichiggelbgreenish yellow
gelbyellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
gelbyellow
grünstichiggelbgreenish yellow
gelbyellow
grünstichiggelbgreenish yellow
gelbyellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünslichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
Z7 Z 7
1919th
2020th
Fortsetzungcontinuation
Aldehydaldehyde
Farbtonhue
1 ,3,3-Ti imethyl-2-methylen-2>,3-dihydroindol-ei>-aldehyd desgl. desgl. desgl. desgl. desgl.1,3,3-Ti imethyl-2-methylene-2 > , 3-dihydroindole-ei> -aldehyde like. Like. Like. Like.
desgl. desgl. desgl.like. like. like.
desgl.the same
desgl. desgl. desgl.like. like. like.
desgl. desgl. dessl. desgl. desgl. desgl. desgl. desgl. desgl.desgl. desgl. like. like. like. like. like. like.
desgl. desgl. desgl.like. like. like.
desgl.the same
desgl.the same
l^-Trimethyl-S-carbomethoxy-2-methylen-2,3-dihydroindol-cu-aldehyd desgl.1-4-Trimethyl-S-carbomethoxy-2-methylene-2,3-dihydroindole-cu-aldehyde the same
1.3,3-Trimethyl-5-chlor-2-me1;hylen-2,3-dihydroindol-cu-aldehyd desgl.1,3,3-Trimethyl-5-chloro-2-me1; ethylene-2,3-dihydroindole-cu-aldehyde the same
1 ,S^-y 2,3-dihydroindol-ω-aldehyd U^-Trimethyl-S-methyW-rnethylen-2,3-dihydroindol-fu-aldehyd ^^y 2,3-dihydroindol-a^aldehyd ^,yy 2-methylen-2,3-dihydroindol·■ω-aldehyd 1 ,S.S-Triniethyl-T-methyl -2-methylen-2,3-dihydroindol-w-aldehyd ^y 2,3-dihydroindol-cu-aldehyd ; i.^-Trimethyl-S-fluor-l-methylen-■ 2.3-dihvdroindol-öj-aldehyd 3-Amino-phenyl-benzyläther1, S ^ -y 2,3-dihydroindole-ω-aldehyde U ^ -trimethyl-S-methyW-methylene-2,3-dihydroindole-fu-aldehyde ^^ y 2,3-dihydroindole-a ^ aldehyde ^, yy 2-methylene-2,3-dihydroindole · ■ ω-aldehyde 1, S.S-triniethyl-T-methyl -2-methylene-2,3-dihydroindole-w-aldehyde ^ y 2,3-dihydroindole-cu-aldehyde ; i. ^ - Trimethyl-S-fluoro-1-methylene ■ 2.3-dihvdroindol-öj-aldehyde 3-Amino-phenyl-benzyl ether
2-Amino-phenyl-benzyläther 4-Aminophenyl-p-methylbenzyläther 4-Aminophenyl-p-chlorbenzyläther 4-Aminophenyl-o-chlor-benzyläther 4-Aminophenyl-m, p-dichlor-benzyläther 2-aminophenyl benzyl ether 4-aminophenyl-p-methylbenzyl ether 4-aminophenyl-p-chlorobenzyl ether 4-aminophenyl-o-chlorobenzyl ether 4-aminophenyl-m, p-dichloro-benzyl ether
5-Aminophenyl-p-methyl-benzyläther S-Aminophenyl-p-chlor-benzyläther 3-Aminophenyl-o-chlor-benzyläther 3-Aminophenyl-m, p-dichlor-benzyläther 5-aminophenyl-p-methyl-benzyl ether S-aminophenyl-p-chlorobenzyl ether 3-aminophenyl-o-chlorobenzyl ether 3-aminophenyl-m, p-dichloro-benzyl ether
2-Aminophenyl-p-methyl-benzyläther 2-Aminophenyl-p-chlor-benzyläther 2-Aminophenyl-m, p-dichlor-benzyl-2-aminophenyl-p-methyl-benzyl ether 2-aminophenyl-p-chloro-benzyl ether 2-aminophenyl-m, p-dichloro-benzyl-
4-Amino-2-methylphenyl-oenzyläther 5-Amino-2-methylphenyl-benzyläther 2-Amino-5-methylphenyl-benzyläther 4-Amino-2-methoxy-phenyl-benzyläther 4-Amino-3-methoxy-phenyl-benzyläther 4-Amino-3-methylphenyl-benzyläther 4-Amino-3-chlor-phenyl-benzyläther 4-Amino-2-chlor-phenyl-benzyläther 4-Amino-2-methyl-phenyl-p-methylbenzyläther 4-Amino-2-methylphenyl-oenzyl ether 5-Amino-2-methylphenyl benzyl ether 2-Amino-5-methylphenyl-benzyl ether. 4-Amino-2-methoxy-phenyl-benzyl ether 4-Amino-3-methoxy-phenyl-benzyl-ether. 4-Amino-3-methyl-phenyl-benzyl-ether 4-Amino-3-chloro-phenyl-benzyl ether 4-Amino-2-chloro-phenyl-benzyl ether 4-Amino-2-methyl-phenyl-p-methylbenzyl ether
5-Amino-2-methyl-phenyl-m, p-dichlorbenzyläther5-amino-2-methyl-phenyl-m, p-dichlorobenzyl ether
4-Amino-2-methoxy-phenylp-methylbenzyläther 4-Amino-2-methoxy-phenyl-p-methylbenzyl ether
2-AInino-5-methyl-phenyl-p-chlorbenzyläther 2-Alino-5-methyl-phenyl-p-chlorobenzyl ether
4-Methylamino-phenylbenzyläther 4-Äthylamino-phenylbenzyläther 3-Aminophenylbenzyläther4-methylamino-phenylbenzyl ether 4-ethylamino-phenylbenzyl ether, 3-aminophenylbenzyl ether
2-Aminophenylbenzyläther
2-Aminophenylbenzyläther2-aminophenylbenzyl ether
2-aminophenylbenzyl ether
3-Aminophenylbenzyläther
4-Aminodiphenyläther3-aminophenylbenzyl ether
4-aminodiphenyl ether
desgl.
desgl.
desgl.
desgl.
desgl.
desgl.the same
the same
the same
the same
the same
the same
grünstichiggelbgreenish yellow
gelbyellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelb grünstichiggelb grünstichiggelb grünstichiggelbgreenish yellow greenish yellow greenish yellow greenish yellow
gelb gelb gelbyellow yellow yellow
gelbyellow
gelbyellow
gelbyellow
rotstichiggelbreddish yellow
gelbyellow
gelbyellow
gelbyellow
gelbyellow
gelbyellow
gelbyellow
rotstichiggelbreddish yellow
gelbyellow
gelb gelb grünstichiggelbyellow yellow greenish yellow
gelb gelbyellow yellow
grünstichiggelb > grünstichiggelb ;greenish yellow > greenish yellow;
grünstichiggelb gelbgreenish yellow yellow
grünstichiggelb grünstichiggelbgreenish yellow greenish yellow
grünstichiggelb :greenish yellow:
grünstichiggelb '*■ greenish yellow '* ■
2121
Fortsetzungcontinuation
Aldehydaldehyde
l,3,3-Trimethyl-7-äthoxy-2-methylen-2,3-dihydroindol-cu-aldehyd l,3,3-Trimethyl-5-benzyl-2-methylen-2,3-dihydroindol-cu-aldehyd l-Äthyl-SJ-dirnethyl^-methylen-23-dihydroindoi-co-aldehyd L3,3,4,6,7-Hexamethyl-2-methylen-2,3-dihydroindol-o»-aldehyd 1 JJ-Trimethyl^-methylen-2,3-dihydroindol-to-aldehyd 1,3,3-Trimethyl-7-ethoxy-2-methylene-2,3-dihydroindole-cu-aldehyde 1,3,3-Trimethyl-5-benzyl-2-methylene-2,3-dihydroindole-cu-aldehyde 1-ethyl-SJ-dirnethyl ^ -methylene-23-dihydroindoi-co-aldehyde L3,3,4,6,7-hexamethyl-2-methylene-2,3-dihydroindole-o »-aldehyde 1 JJ-Trimethyl ^ -methylene-2,3-dihydroindol-to-aldehyde
2222nd
y 2,3-dihydroindol-o>-aldehyd l^^-Trimethyl-S-carbomethoxy-2-methylen-2,3-dihydroindol-co-aldehyd 1,3,3-Trimethyl-2-methylen-2,3-dihydroindoI-cu-aldehyd desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl.y 2,3-dihydroindole-o> -aldehyde l ^^ - trimethyl-S-carbomethoxy-2-methylene-2,3-dihydroindole-co-aldehyde 1,3,3-trimethyl-2-methylene-2,3-dihydroindol-cu-aldehyde like. like. like. like. like. like. like. like. like. like. like. like. like. like.
2,3-dihydroindol-oj-aldehyd desgl. desgl. desgl.2,3-dihydroindole-oj-aldehyde like. like. like.
1 J.^-Trimethyl-S-carbomethoxy-2-methylen-2,3-dihydroindol-oj-aldehyd desgl.1 J. ^ - Trimethyl-S-carbomethoxy-2-methylene-2,3-dihydroindole-oj-aldehyde the same
desgl.the same
l-.^-Trimethyl-V-phenoxy-I-methylen-2,3-dihydroindol-w-aldehyd desgl.l -. ^ - Trimethyl-V-phenoxy-I-methylene-2,3-dihydroindole-w-aldehyde the same
desgl.the same
desgl.the same
desgl.the same
desgl.the same
desgl.the same
desgl.the same
desgl.the same
HpcolHpcol
AminAmine
4-Aminodiphenyläther4-aminodiphenyl ether
desgl. desgl.the same.
desgl. 2-Aminodiphenylätherlikewise. 2-aminodiphenyl ether
desgl.the same
desgl.
4-Amino-4'-methyl-diphenylätherthe same
4-amino-4'-methyl-diphenyl ether
4-Amino-4/-äthyl-diphenyläther4-amino-4 / ethyl diphenyl ether
4-Amino^'-tertiär-butyl-diphenylather4-Amino ^ '- tertiary butyl diphenyl ether
4-Amino-4'-cyciohexyl-diphenylather4-amino-4'-cyclohexyl diphenyl ether
4-Amino-2'-methyl-diphenyläther4-amino-2'-methyl-diphenyl ether
4-Amino-3'-methyl-diphenyIäther4-Amino-3'-methyl-diphenyl ether
4-Amino-4'-methoxy-diphenyläther4-amino-4'-methoxy-diphenyl ether
4-Amino-3'-methoxy-diphenyläther4-amino-3'-methoxy-diphenyl ether
4-Amino-4'-äthoxy-diphenyläther4-amino-4'-ethoxy-diphenyl ether
4-Amino-4'-acetylamino-diphenyläther4-amino-4'-acetylamino-diphenyl ether
4-Amino-4'-hydroxy-diphenyläther4-amino-4'-hydroxy-diphenyl ether
4-Amino-4'-nitro-diphenyläther4-amino-4'-nitro-diphenyl ether
4-Amino4'-chlor-diphenyläther4-amino4'-chloro-diphenyl ether
4-Amino-2'-chlor-diphenyläther4-amino-2'-chloro-diphenyl ether
4-Amino-3 '-chlor-diphenyläther4-amino-3'-chloro-diphenyl ether
4-Aminophenyl-a-naphthyläther4-aminophenyl-a-naphthyl ether
4-Aminophenyl-^-naphthyläther4-aminophenyl - ^ - naphthyl ether
4-Amino-2',3',5'-trimethyldiphenyläther4-amino-2 ', 3', 5'-trimethyldiphenyl ether
4-Amino-4'-äthyl-dipheny lather4-Amino-4'-ethyl-diphenyl ether
4-Amino-4'-tert.-butyl-diphenyläther4-amino-4'-tert-butyl diphenyl ether
4-Amino-4'-methoxy-diphenyläther4-amino-4'-methoxy-diphenyl ether
4-Aminophenyl-a-naphthyläther4-aminophenyl-a-naphthyl ether
^-Amino-phenyl^'-methyldiphenyl-^ -Amino-phenyl ^ '- methyldiphenyl-
4-Amino-phenyl-4'-methox Y-4-Amino-phenyl-4'-methox Y-
diphenylätherdiphenyl ether
4-Amino-phenyl-a-naphthyläther4-Amino-phenyl-a-naphthyl ether
4-Aminodiphenylmethan4-aminodiphenylmethane
4-Amino-diphenyläther4-amino-diphenyl ether
4-Aniinophenylbenzyläther4-Aniinophenylbenzyläther
3-Aminophenylbenzyläther3-aminophenylbenzyl ether
Anilinaniline
p-Toluidinp-toluidine
m-Toluidinm-toluidine
o-Anisidino-anisidine
m-Anisidinm-anisidine
n-Anisidinn-anisidine
Farbtonhue
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
gelbyellow
gelbyellow
gelbyellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
gelbyellow
gelbyellow
gelbyellow
grünstichiggelbgreenish yellow
gelbyellow
gelbyellow
gelbyellow
gelbyellow
rotstichiggelbreddish yellow
grünstichiggelbgreenish yellow
gelbyellow
gelbyellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
gelbyellow
grünstichiggelbgreenish yellow
grünstichiggelb grünstichiggelb grünstichiggelb grünstichiggelbgreenish yellow greenish yellow greenish yellow greenish yellow
grünstichiggelbgreenish yellow
grünstichiggelb gelbgreenish yellow yellow
gelbyellow
gelbyellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
gelbyellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
2424
Fortsetzung AldehydContinuation of aldehyde
Ij. I Ij. I.
AminAmine
FarblanColor lan
Fortsetzung AldehydContinuation of aldehyde
1,3,3-Trimethyl-7-benzyloxy-2-methylen-2,3-dihydroindol-iu-aldehyd desgl.1,3,3-Trimethyl-7-benzyloxy-2-methylene-2,3-dihydroindol-iu-aldehyde the same
desgl.the same
Gemisch aus 1 ^-TrimethyM-benzyloxy-2-inethyIen-2,3-dihydroindo)-f/)-aldehyd Mixture of 1 ^ -trimethyM-benzyloxy-2-inethylene-2,3-dihydroindo) -f /) - aldehyde
1,3.3-Trimethyl-6-benzyloxy-2-methylen-2,3-dihydroindol-o>-aldehyd desgl. (Gemisch) U'J-Trimethyl-S-benzyloxy-I-methylen-2,3-dihydroindol-öj-aldehyd desgl.1,3,3-Trimethyl-6-benzyloxy-2-methylene-2,3-dihydroindole-o> -aldehyde the same. (mixture) U'J-Trimethyl-S-benzyloxy-I-methylene-2,3-dihydroindole-öj-aldehyde the same
i!3-.3-Trimethyl-7-benzyl-2-methylen-2,>dihydroindol-ro-aldehyd !l,3,3-Trimethyl-5-(p-methylbenzyloxy)-2-methylen-2,3-dihydroindol-cu-aldehyd l,:l,3-Trimethyl-5-benzy!oxy-2-methylen-2,3-dihydroindol-(u-aldehyd desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. dtisgl. desgl. desgl. desgl.i! 3-.3-Trimethyl-7-benzyl-2-methylene-2,> dihydroindol-ro-aldehyde ! 1,3-trimethyl-5- (p-methylbenzyloxy) -2-methylene-2,3-dihydroindol-cu-aldehyde 1,3-trimethyl-5-benzyoxy-2-methylene-2, 3-dihydroindole- (u-aldehyde like. Like. Like. Like. Like. Like.
l.?,3-Trimclhyl-5-(o-chlorbenzyloxy)-2-methylen-2,3-dihydroindol-a>-aldehyd ■|,3,3-Trimetffyl-7-(p-chlorbenzyloxy)-2-methylen-2,3-dihydroindol-f/j-aldehyd I, J^-Trimethyl-S-methyl-^-benzyloxy-2-methylen-2,3-dihydroindol-fu-aldehyd Gemisch aus:l.?,3- Trimethyl-5-(o-chlorbenzyloxy)-2-methylene-2,3-dihydroindole-a> -aldehyde 3,3-trimethyl-7- (p-chlorobenzyloxy) -2-methylene-2,3-dihydroindole-f / j-aldehyde I, J ^ -trimethyl-S-methyl- ^ - benzyloxy-2-methylene-2,3-dihydroindole-fu-aldehyde Mixture of:
!,S^Trimeyyyy 2-methylen-2,3-dihydroindol-m-aldehyd und l.S.S-Trimethyl-o-melhoxyö-benzyloxy-2-methylen-2,3-dihydroindol-«)-aldehyd Gemisch a js:!, S ^ Trimeyyyy 2-methylene-2,3-dihydroindole-m-aldehyde and 1.S.S-trimethyl-o-melhoxyö -benzyloxy-2-methylene-2,3-dihydroindole- «) aldehyde Mixture a js:
1, :l,3-Trimethyl-5-methyl-6-benzyloxy-1,: l, 3-trimethyl-5-methyl-6-benzyloxy-
2-methylen-2,3-dihydroindol-f»-aldehyd und l,3.3-Trime!hyl-5-methyl-4-benzyIoxy-2-methylene-2,3-dihydroindole-f »-aldehyde and 1,3.3-trimethyl-5-methyl-4-benzyIoxy-
2-methylen-2,3-dihydroindol-f/)-aldehyd J,3,3-Trimethyl-7-(p-methylbenzyloxy)-2-methylene-2,3-dihydroindole-f /) - aldehyde J, 3,3-trimethyl-7- (p-methylbenzyloxy) -
2-methylen-2,3-dihydroindol-fi)-aldehyd l,3,3-Trimethyl-7-(o-chlorbenzyloxy)-melhylen-2,3-dihydroindol-f/)-aldehyd 2-methylene-2,3-dihydroindole-fi) aldehyde 1,3,3-Trimethyl-7- (o-chlorobenzyloxy) -melhylen-2,3-dihydroindole-f /) aldehyde
2-Methyl-2,3-dihydroindol2-methyl-2,3-dihydroindole
p-Anisidin 3,4-Dimethoxyanilinp-anisidine 3,4-dimethoxyaniline
2-Methyl-2,3-dihydroindol2-methyl-2,3-dihydroindole
p-Anisidin 2-Methyl-2.3-dihydroindolp-anisidine 2-methyl-2,3-dihydroindole
p-Anisidin 4-Aminophenylbenzylätherp-anisidine 4-aminophenylbenzyl ether
2-Methyl-2,3-dihydroindol 4-Amino-1,3-dimethoxybenzoI2-methyl-2,3-dihydroindole 4-amino-1,3-dimethoxybenzoI
4-Amino-1,4-dimethoxybenzol4-amino-1,4-dimethoxybenzene
3,4-Dimethoxyanilin3,4-dimethoxyaniline
p-Chloranilinp-chloroaniline
p-Fluoranilirp-fluoroanilir
2,4,5-Trimethylanilin2,4,5-trimethylaniline
6-Amino-3-methoxytoluol6-amino-3-methoxytoluene
5-Amino-2-acetylaminoanisol5-amino-2-acetylaminoanisole
o-Phenetidino-phenetidine
3,4-Dicyananilin3,4-dicyananiline
SulfanilsäureamidSulfanilic acid amide
4-Aminobenzamid4-aminobenzamide
p-Phenetidinp-phenetidine
4-Aminoacetanilid4-aminoacetanilide
p-Toluidinp-toluidine
N-Methyl-p-anisidinN-methyl-p-anisidine
2-Methyl-2.3-dihydroindol2-methyl-2,3-dihydroindole
desgl. desgl.the same.
desgl. desgl. desgl.like. like. like.
desgl desgl. desgl.the same the same the same
grünstichiggelb rotstichiggelbgreenish yellow reddish yellow
grünstichiggelbgreenish yellow
grünstichiggelb grünstichiggelbgreenish yellow greenish yellow
grünstichiggelb grünstichiggelbgreenish yellow greenish yellow
grünstichiggelb goldgelbgreenish yellow golden yellow
goldgelb goldgelb gelb grünstichiggelb gelb gelb rotstichiggelb gelb goldgelb gelb gelb gelb gelb grünstichiggelb grünstichiggelb gelbgolden yellow golden yellow yellow greenish yellow yellow yellow reddish yellow yellow golden yellow yellow yellow yellow yellow greenish yellow greenish yellow yellow
grünstichiggelb gelbgreenish yellow yellow
gelbyellow
gelbyellow
grünstichiggelbgreenish yellow
gelbyellow
2:72: 7
Fortsetzungcontinuation
Aldehydaldehyde
2-methylen-2,3-dihydroindol-w-aldehyd l,3,3-Tt"imethyl-5-methyl-7-(p-methylbenzyloxy)-2-methylen-2,3-dihydroiiidoi-fj-aldehyd l,3,3-Trimethyl-5-(4'-methylphenoxy)-2-methylen-2,3-dihydroindol-io-aldehyd l,3,3-Trimethyl-5-(4'-methoxyphenoxy)-2-methylen-2,3-dihydroindol-o)-aldehyd I,3,3-Trimethyl-7-(4'-melhoxyphenoxy)-2-methylen-2,3-dihydroindol-o)-aldehyd 1,3,3-Trimethyl-5-(4 -chlorphenoxy)-2-methylen-2,3-dihydroindo!-fu-aldehyd l,3,3-Trimethyl-7-(3'-methylphenoxy)-2-melhylen-2,3-dihydroindol-»j-aldehyd l,3-3-Trimethyl-5-(3'-methoxyphenoxy)-2-methylen-2,3-dihydroindol-tu-aldehyd l,^,3-Trimethyl-5-(i-naphlhyloxy-2-methylen-2,3-dihydrointi <il-fu-aldehyd 1,3,3-Trimethyl-5-(4'-äthy lphenoxy )-2-methylen-2,3-dihydroindol-(u-aldehyd l,3,3-Trimethyl-5-(p-methylbenzyloxy)-2-methylen-2,3-dihydroindol-f.)-aldehyd l,3.3-Trimethyl-5-(o-chlorbenzyloxy)-2-methylen-2,3-dihydroindol-f/j-aldehyd l,3,3-Trimethyl-7-(p-chlorbenzyloxy)-2-methylen-2,3-dihydroiridol-(u-aldehyd l,3,3-Trimethy]-5-methyl-7-be:nzyloxy-2-methylen-2,3-dihydΓoindol-ω-aldehyd Gemisch aus:2-methylene-2,3-dihydroindole-w-aldehyde 1,3,3-Tt "imethyl-5-methyl-7- (p-methylbenzyloxy) -2-methylene-2,3-dihydroiiidoi-fj-aldehyde 1,3,3-Trimethyl-5- (4'-methylphenoxy) -2-methylene-2,3-dihydroindole-io-aldehyde 1,3,3-Trimethyl-5- (4'-methoxyphenoxy) -2-methylene-2,3-dihydroindole-o) -aldehyde 1,3,3-Trimethyl-7- (4'-melhoxyphenoxy) -2-methylene-2,3-dihydroindole-o) -aldehyde 1,3,3-trimethyl-5- (4-chlorophenoxy) -2-methylene-2,3-dihydroindo! -Fu-aldehyde 1,3,3-Trimethyl-7- (3'-methylphenoxy) -2-methylene-2,3-dihydroindole- »j-aldehyde 1,33-trimethyl-5- (3'-methoxyphenoxy) -2-methylene-2,3-dihydroindol-tu-aldehyde l, ^, 3-trimethyl-5- (i-naphlhyloxy-2-methylene-2,3-dihydrointi <il-fu-aldehyde 1,3,3-trimethyl-5- (4'-ethy lphenoxy) -2-methylene-2,3-dihydroindole- (u-aldehyde 1,3,3-Trimethyl-5- (p-methylbenzyloxy) -2-methylene-2,3-dihydroindole-f.) aldehyde 1,3,3-Trimethyl-5- (o-chlorobenzyloxy) -2-methylene-2,3-dihydroindole-f / j-aldehyde 1,3,3-Trimethyl-7- (p-chlorobenzyloxy) -2-methylene-2,3-dihydroiridol- (u-aldehyde 1,3,3-trimethyl] -5-methyl-7-be: nzyloxy-2-methylene-2,3-dihydΓoindole-ω-aldehyde Mixture of:
lJ^-TrirnethyM-melhoxy-S-benzyloxy-2-melhylen-2,3-dihydroindol-fj)-aldehyd lJ ^ -TrirnethyM-melhoxy-S-benzyloxy-2-melhylen-2,3-dihydroindole-fj) -aldehyde
l,3-3-Trimethyl-6-metho>iy-5-benzyloxy-2-methylen-2,3-dihydroindol-ro-aldehyd Gemisch aus:1,33-trimethyl-6-metho> iy-5-benzyloxy-2-methylene-2,3-dihydroindole-ro-aldehyde Mixture of:
U^^-Trimethyl-S-methyl-o-benzyloxy-2-methylen-2,3-dihydroindol-fü-aldehyd undU ^^ - Trimethyl-S-methyl-o-benzyloxy-2-methylene-2,3-dihydroindole-pu-aldehyde and
2-methylen-2,3-dihydroindol-m-aldehyd l,3.3-Trimelhyl-7-(p-methylbenzyloxy)-2-methylen-2,3-dihydroindol-(o-aldehyd l,3,3-Trimethyl-7-(o-chlorbenzyloxy)-2-melhylen-2,3-dihydroindol-fi)-aIdehyd l,3.3-Trimethyl-5-benzyloxy-7-methyl-2-methylen-2,3-dihydroindol-oj-aldehyd l,3,3-Trimethyl-5-methyl-7-(p-methylbenzyloxyj-2-methylen-2,3-dihydroindcl-«> -aldehyd l,3,3-Trimethyl-5-(4'-mcthylphenoxy)-2-methylen-2,3-dihydroindol-f»-aldehyd l,3,3-Trimethyl-5-(4'-methoxyphenoxy)-2-methylen-2,3-dihydromdol-fu-aldehyd l,3,3-Trimethyl-7-(4'-methoxyphenoxy)-2-methylen-2,3-dihydroindol-f«-aldehyd l,3,3-Trimethyl-5-(4'-chlorphenoxy)-2-methylen-2,3-dihydroindol-(i)-aldehyd l,3,3-Trimethyl-7-(3'-methylphenoxy)-2-methvlen-2,3-dihydroindol-fjj-aldehyd 2-Methyl-2,3-dihydroindol desgl.2-methylene-2,3-dihydroindole-m-aldehyde 1,3,3-trimelhyl-7- (p-methylbenzyloxy) -2-methylene-2,3-dihydroindole- (o-aldehyde 1,3,3-Trimethyl-7- (o-chlorobenzyloxy) -2-methylene-2,3-dihydroindole-fi) aldehyde 1,3,3-Trimethyl-5-benzyloxy-7-methyl-2-methylene-2,3-dihydroindole-oj-aldehyde 1,3,3-Trimethyl-5-methyl-7- (p-methylbenzyloxy-2-methylene-2,3-dihydroindcl - «> -aldehyde 1,3,3-trimethyl-5- (4'-methylphenoxy) -2-methylene-2,3-dihydroindole-f »-aldehyde 1,3,3-trimethyl-5- (4'-methoxyphenoxy) -2-methylene-2,3-dihydromdol-fu-aldehyde 1,3,3-Trimethyl-7- (4'-methoxyphenoxy) -2-methylene-2,3-dihydroindole-f «-aldehyde 1,3,3-Trimethyl-5- (4'-chlorophenoxy) -2-methylene-2,3-dihydroindole- (i) -aldehyde 1,3,3-Trimethyl-7- (3'-methylphenoxy) -2-methylene-2,3-dihydroindole-fjj-aldehyde 2-methyl-2,3-dihydroindole like.
desgl.the same
desgl.the same
desgl.the same
desgl.the same
desgl.the same
desgl.the same
desgl.the same
desgl.the same
p-Anisidin desgl.p-anisidine the like.
desgl.the same
desgl.the same
desgl. desgl. desgl.like. like. like.
desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl. desgl.like. like. like. like. like. like. like. like. like.
2828
Farbtonhue
giünstichiggelbfavorable yellow
grünstichiggelb >greenish yellow>
grünslichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
gelbyellow
gelbyellow
gelbyellow
gelb ryellow r
gelbyellow
gelbyellow
gelb gelb gelb gelb gelb gelb gelb gelb gelb gelbyellow yellow yellow yellow yellow yellow yellow yellow yellow yellow
2,3-dihydroindol-fj)-aldehyd2,3-dihydroindole-fj) -aldehyde
Man erwärmt eine Mischung von 13,3 Gewichtsteilen 2-Methyl-2,3-dihydroindol, 10 Volumteilen Ameisensäure und 120 Volumteilen Chlorbenzoi langsam unter Rühren auf zuletzt 140', destilliert dabei ca. 65 Volumteile Flüssigkeit ab und kühlt dann den Destillationsrückstand auf 30° ab.A mixture of 13.3 parts by weight of 2-methyl-2,3-dihydroindole and 10 parts by volume is heated Formic acid and 120 parts by volume of chlorobenzene slowly while stirring to 140 'at last, about 65 parts by volume of liquid distilled off and then cooled Distillation residue to 30 °.
Dann werden 16 Gewichtsteile Phosphoroxychlorid eingerührt und anschließend 27,9 Gewichidteile 1,3,3 - Trimethyl - 5 - benzyloxy - 2 - methylen - 2,3 - dihydroindol unter Rühren eingetropft. Man rührt 15 Minuten ohne Heizung, dann 3 Stunden bei 60r.16 parts by weight of phosphorus oxychloride are then stirred in and then 27.9 parts by weight of 1,3,3-trimethyl-5-benzyloxy-2-methylene-2,3-dihydroindole are added dropwise with stirring. The mixture is stirred for 15 minutes without heating, then for 3 hours at 60.degree .
-CH,-O Der Farbstoff wird vom Lösungsmittel abgetrennt, aus 1000 Volumteilen Wasser umgelöst und mit Siedesalz ausgefällt. Er färbt Materialien aus Polyacrylnitril, sauer modifizierten Polyestern und sauei modifiziertem Polyamid in klaren grünstichiggelben Tönen von sehr guten Licht- und Naßechtheiten Der Farbstoff ist identisch mit dem in der Tabelle zu Beispiel 1 erwähnten Farbstoff aus 1,3,3-Trimethyl· 5 - benzyloxy - 2 - methylen - 2,3 - dihydroindol - <■> - aide hyd und 2-Methyl-2,3-dihydroindol und hat die For mel:-CH, -O The dye is separated from the solvent, redissolved from 1000 parts by volume of water and precipitated with evaporated salt. It dyes materials made of polyacrylonitrile, acid-modified polyesters and acid-modified polyamide in clear greenish-yellow shades of very good light and wet fastness properties. The dye is identical to the 1,3,3-trimethyl.5-benzyloxy dye mentioned in the table for Example 1 - 2 - methylene - 2,3 - dihydroindole - <■> - aide hyd and 2-methyl-2,3-dihydroindole and has the formula:
CH = CH-NCH = CH-N
CH,CH,
ClCl
Einen wertvollen gelben Farbstoff erhält man auch, wenn man statt 1,3,3 - Trimethyl - 5 - benzyloxy-2-methylin-2,3-dihydroindol die äquivalente Menge 2,3.3-Trimethyl-5-benzyloxyindolenin einsetzt.A valuable yellow dye is also obtained if, instead of 1,3,3 - trimethyl - 5 - benzyloxy-2-methylin-2,3-dihydroindole, one uses the equivalent amount of 2,3,3-trimethyl-5-benzyloxyindolenine is used.
Ein Gewebe aus Polyacrylnitril wird mit einer Druckpaste bedruckt, die in folgender Weise hergestellt wurde:A polyacrylonitrile fabric is printed with a printing paste, which is produced in the following manner would:
30 Gewichtsteile des in Beispiel 2 beschriebenen Farbstoffs, 50 Gewichtsteile Thiodiät'liylenglykol. 6s 30 Gewichtsteile Cyclohexanol und 30 Gewichtsteile 30%igcr Essigsäure werden mit 330 Gcwichtsleilen heißem Wasser übergössen und die erhaltene Lösung zu 500 Gewichtsteilen Kristallgummi (Gummi arab cum als Verdickungsmittel) gegeben. Schließlich we den noch 30 Gewichtsteile Zinknitratlösung zugesets Der erhaltene Druck wird getrocknet, 30Minutf gedämpft und anschließend gespült. Man erhä einen gelben Druck von sehr guten Echtheitseigei schäften.30 parts by weight of the dye described in Example 2, 50 parts by weight of Thiodiät'liylenglykol. 6s 30 parts by weight of cyclohexanol and 30 parts by weight of 30% acetic acid are mixed with 330 parts by weight Poured over hot water and add 500 parts by weight of crystal gum (gum arabic) to the resulting solution cum as a thickener). Finally, 30 parts by weight of zinc nitrate solution are added The pressure obtained is dried, steamed for 30 minutes and then rinsed. You get a yellow print with very good authenticity properties.
Sauer modifizierte Polyglykoltcrephthalatrase werden bei 20" C im Flottenverhältnis 1 :40 in wäßrig Bad eingebracht, das pro Liter 3 bis 10 e Natriul sulfat, 0,1 bis 1 g Olcylpolyglykoläther (50"Mol Ätli lenoxid), 0—15 g Dimcthyl-benzyldodecylammoniui chlorid und 0,15 g des in Beispiel 1 formelmätAcid modified polyglycol crephthalatase become aqueous at 20 ° C. in a liquor ratio of 1:40 Bath introduced, the per liter 3 to 10 e Natriul sulfate, 0.1 to 1 g olcyl polyglycol ether (50 "mol Ätli lenoxide), 0-15 g of dimethyl-benzyldodecylammonium chloride and 0.15 g of the formula in Example 1
ή Irή Ir
beschriebenen Farbstoffs enthält und mit Essigsäure pH 4 bis 5 eingestellt wurde. Man erhitzt innerhalb 30 Minuten auf 1000C und hält das Bad 60 MinutenContains the dye described and was adjusted to pH 4 to 5 with acetic acid. The mixture is heated to 100 ° C. within 30 minutes and the bath is kept for 60 minutes
bei dieser Temperatur. Anschließend werden die Fasern gespült und getrocknet. Man erhält eine gelbe Färbung von sehr guten Echtheitseigenschaften.at this temperature. The fibers are then rinsed and dried. A yellow one is obtained Coloring with very good fastness properties.
Polyacrylnitrilfasern werden bei 40° C im Flottenverhältnis 1:40 in ein wäßriges Bad eingebracht, das pro Liier 0,75 g 30%ige Essigsäure, 0,38 g Natriumacetat und 0,15 g des in Beispiel 2 beschriebenen ι ο guten Echtheitseigenschaften. Farbstoffs enthält. Man erhitzt innerhalb von 20 bisPolyacrylonitrile fibers are at 40 ° C in the liquor ratio 1:40 placed in an aqueous bath containing 0.75 g of 30% acetic acid, 0.38 g of sodium acetate per Liier and 0.15 g of the ι ο good fastness properties described in Example 2. Contains dye. It is heated within 20 to
30 Minuten zum Sieden und hält das Bad 30—60 Minuten bei dieser Temperatur. Nach dem Spülen und Trocknen erhält man eine gelbe Färbung mit sehr30 minutes to simmer and lasts 30-60 minutes in the bath at this temperature. After rinsing and drying, a yellow color with very is obtained
Aus 15 Gewichtsteilen des in Beispiel 2 genannten Farbstoffs, 15 Gewichtsteilen Polyacrylnitril und 70 Gewichtsteilen Dimethylformamid wird eine Stammlösung hergestellt, die zu einer üblichen Spinnlösung von Polyacrylnitril zugesetzt und in bekannter Weise versponnen wird. Man erhält eine grünstichiggelbe Färbung von sehr guten Echtheitseigenschaften.From 15 parts by weight of that mentioned in Example 2 Dye, 15 parts by weight of polyacrylonitrile and 70 parts by weight of dimethylformamide is one Stock solution prepared, which is added to a conventional spinning solution of polyacrylonitrile and known in Way is spun. A greenish yellow coloration with very good fastness properties is obtained.
Sauer modifizierte synthetische Polyamidfasern werden bei 40° im Floltenverhältnis 1:40 in ein wäßriges Bad eingebracht, das pro Liter 10 g Natriumacetat, und 0,3 g des in der Tabelle zu Beispiel 1 erwähnten aus 1,3,3 - Trimethyl - 5 - (p - methoxyphenoxy) - 2 - methylen-2,3-dihydro .ndol-tu-aldehyd und 2-Methyl-Acid modified synthetic polyamide fibers are converted into an aqueous one at 40 ° in a flute ratio of 1:40 Introduced bath containing 10 g of sodium acetate per liter, and 0.3 g of that mentioned in the table for Example 1 from 1,3,3 - trimethyl - 5 - (p - methoxyphenoxy) - 2 - methylene-2,3-dihydro .ndol-tu-aldehyde and 2-methyl-
1 bis 5 g Oleylpolyglykoläther {50 Mol Äthylenoxid) 25 2,3-dihydroindol dargestellten Farbstoffs der Formel1 to 5 g of oleyl polyglycol ether (50 mol of ethylene oxide) 25 2,3-dihydroindole represented dye of the formula
H3CO-H 3 CO-
CH=CHCH = CH
ClCl
enthält und mit Essigsäure auf pH 4—5 eingestellt wurde. Man erhitzt innerhalb von 30 Minuten auf 98° und hält das Bad 60 Minuten bei dieser Temperatur. Anschließend wurden die Fasern gespült und getrocknet. Man erhält eine grünstichiggelbe Färbung von guten Echtheitseigenschaften.and adjusted to pH 4-5 with acetic acid would. The mixture is heated to 98 ° over the course of 30 minutes and the bath is kept at this temperature for 60 minutes. The fibers were then rinsed and dried. A greenish yellow color is obtained of good fastness properties.
Polyacrylnitrilfasern wurden im Flottenverhältnis des in der Tabelle zu Beispiel \ erwähnten ausPolyacrylonitrile were mentioned the liquor ratio in the Table of Example \ from
1 :10 in ein Perchloräthylenbad eingebracht, welches 1,3,3 - Trimethyl - 2 - methylen - 2,3 - dihydroindol-1:10 placed in a perchlorethylene bath containing 1,3,3 - trimethyl - 2 - methylene - 2,3 - dihydroindole
pro Liter 1 g ölsäureäthanolamid, 1 g des Umset- m-aldehyd und 4-Amino-4'-tertiärbutyl-diphenyl-per liter 1 g of oleic acid ethanolamide, 1 g of the converted m-aldehyde and 4-amino-4'-tert-butyl-diphenyl
zungsproduktes von 1 Mol Oleylalkohol mit 20 Mol 45 äther dargestellten Farbstoffs der Formel Äthylenoxid, 8 g Wasser und 1 g Eisessig sowie 1 gtion product of 1 mole of oleyl alcohol with 20 moles of 45 ether represented dye of the formula Ethylene oxide, 8 g of water and 1 g of glacial acetic acid and 1 g
CH3 CH 3
0ctCHl 0ct CHl
\An\On
ClCl
gespült und getrocknet. Man erhält eine grünstichiggelbe Färbung von sehr guten Echtheitseigenschaften.rinsed and dried. A greenish yellow coloration with very good fastness properties is obtained.
CH,CH,
enthält. Man erhitzt das Färbebad unter lebhafter Bewegung der Flotte im geschlossenen Färbeapparat 60 Minuten auf 100°. Anschließend werden die Faserncontains. The dyebath is heated in the closed dyeing apparatus with vigorous movement of the liquor 60 minutes at 100 °. Then the fibers
Der in der Tabelle zu Beispiel 1 erwähnte Farbstoff aus 1,3,3 - Trimethyl - 7 - benzyloxy - 2 - methylen-2,3-dihydroindolaldehyd und p-Anisidin wird in üblicher Weise in die Farbbase übergeführt. 25 Teile dieser Farbbase werden in 150 Teilen Perchloräthylen suspendiert und 65 Teile Butyrolacton und hierauf 15 Gewichtsteile 2-Älhylcapronsäure zugesetzt. Der Farbstoff löst sich mit gelbem Farbton. Man läßt die Lösung noch eine Stunde bei 50° C rühren und saugt sie., nachdem sie wieder auf Raumtemperatur abgekülhlt worden ist, ab. Man erhält eine stabile Lösung, die hervorragend zum Färben von Polyacrylnitrilmaterialien aus Chlorkohlenwasserstofflösungen geeignet ist.The dye of 1,3,3 - trimethyl - 7 - benzyloxy - 2 - methylene-2,3-dihydroindolaldehyde mentioned in the table for Example 1 and p-anisidine is converted into the color base in the usual way. 25 parts of this color base are perchlorethylene in 150 parts suspended and 65 parts of butyrolactone and then 15 parts by weight of 2-ethylcaproic acid added. the Dye dissolves with a yellow tint. The solution is allowed to stir for a further hour at 50 ° C. and suction them. after being cooled back to room temperature has been from. A stable solution is obtained which is excellent for coloring polyacrylonitrile materials from chlorinated hydrocarbon solutions is suitable.
\χ/ «τ in 983 Teilen Perchloräthylen besteht. Das\ χ / «τ consists of 983 parts of perchlorethylene. The
50 Teile Fasergarn aus anionisch modifiziertem ^assei , ]ebhafter Flottenzirkulation innerhalb50 parts of fiber yarn made from anionically modified ^ assei, ] ebha f te r liquor circulation within
Polyacrylnitril werden bei 22° in ein Färbebad ge- Bau wira * ^ ^0 gebracht und eme Stunde bracht, das aus einer Mischuni von 4 Teilen der im s von JU Mi mr gehalten. Nach dieser ZeitPolyacrylonitrile are placed in a dyebath at 22 ° and brought an hour which is kept from a mixture of 4 parts of the im s of JU Mi mr . After this time
Beispiel 9 beschriebenen Perchloräthylenfarbstoff- bei α«»<L. tt getrennt und das Garn im LuftstromPerchlorethylene dye described in Example 9 at α «» <L. tt separated and the yarn in the air stream
... F ,^-. >-«_-_-. wi ι.,™;,} ΛΤριΊρπ des Wird die Motte dUo^ ·„„, t,or™t Mon ^rV1BIt... F , ^ -. > - «_-_-. wi ι., ™ ;,} ΛΤριΊρπ des Will the moth dU o ^ · "", t, o r ™ t Mon ^ rV 1 BIt
lösung, 4 Teilen ülsäureäthanolamid, 4 Teilen des wrdd'^i°„ dem° Lösungsmittel befreit .Man erhält
Umsetzungsprodulctes von 1 Mol Oleylakohol mit von a^nae
iftMni sthvlenoxid. 1 Teil Eisessig und 8Teilen einegrunsticmggsolution, 4 parts ülsäureäthanolamid, 4 parts of the wrdd '^ i ° "° the solvent removed .MAN receives Umsetzungsprodulctes of 1 mole of oleyl alcohol with from a ^ nae
iftMni steel oxide. 1 part glacial acetic acid and 8 parts a grunsticmgg
UmsetzungsprouImplementation Prou
20 Mol Äthylenoxid, 1 Teil Eisessig20 moles of ethylene oxide, 1 part of glacial acetic acid
Claims (5)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702040653 DE2040653C3 (en) | 1970-08-17 | Methine dyes, processes for their production and their use for dyeing certain polymers, copolymers, leather, tannin cotton, printing pastes and fibers containing lignin | |
| NL7111141A NL7111141A (en) | 1970-08-17 | 1971-08-12 | |
| CH1192971D CH1192971A4 (en) | 1970-08-17 | 1971-08-13 | |
| CA120,510A CA989397A (en) | 1970-08-17 | 1971-08-13 | Methine dyestuffs |
| AT233072A AT323700B (en) | 1970-08-17 | 1971-08-13 | PROCESS FOR COLORING AND PRINTING MOLDED BODIES |
| CH938575A CH572511A5 (en) | 1970-08-17 | 1971-08-13 | |
| CH1192971A CH573011B5 (en) | 1970-08-17 | 1971-08-13 | |
| AT710571A AT305460B (en) | 1970-08-17 | 1971-08-13 | Process for the production of new methine dyes |
| JP46061693A JPS5115536B1 (en) | 1970-08-17 | 1971-08-16 | |
| US00172585A US3786047A (en) | 1970-08-17 | 1971-08-17 | Methine dyestuffs |
| BE771401A BE771401A (en) | 1970-08-17 | 1971-08-17 | METHINIC COLORANTS AND THEIR PROCESS FOR OBTAINING |
| GB3849471A GB1319177A (en) | 1970-08-17 | 1971-08-17 | Methine dyestuffs |
| FR7130009A FR2104448A5 (en) | 1970-08-17 | 1971-08-17 | |
| JP50138811A JPS5192369A (en) | 1970-08-17 | 1975-11-20 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702040653 DE2040653C3 (en) | 1970-08-17 | Methine dyes, processes for their production and their use for dyeing certain polymers, copolymers, leather, tannin cotton, printing pastes and fibers containing lignin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2040653A1 DE2040653A1 (en) | 1972-02-24 |
| DE2040653B2 DE2040653B2 (en) | 1976-10-07 |
| DE2040653C3 true DE2040653C3 (en) | 1977-05-18 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2040872C3 (en) | Hydrazone dyes | |
| EP0029136B1 (en) | Quaternary and basic azomethine compounds, process for their preparation and their use as dyestuffs | |
| DE2926183A1 (en) | CATIONIC DYES | |
| DE2520816C3 (en) | Methine dyes | |
| DE2040652C3 (en) | Methine dyes | |
| DE2929285C2 (en) | Cationic oxazine dyes | |
| DE1569748C3 (en) | Aminodiphenyl-indolyl-methane dyes free of sulfonic acid and carboxylic acid groups, their preparation and use | |
| DE2040653C3 (en) | Methine dyes, processes for their production and their use for dyeing certain polymers, copolymers, leather, tannin cotton, printing pastes and fibers containing lignin | |
| US3786047A (en) | Methine dyestuffs | |
| DE2031202C3 (en) | Hydrazone dyes, processes for their production and their use for dyeing and printing polyacrylonitrile, vinylidenecyanide, acid-modified polyester and polyamide fibers, leather, taiuiierter cotton, fibers containing lignin, writing fluids and printing pastes | |
| DE2044619C3 (en) | Basic azolindoline dyes, processes for their production and their use for dyeing and printing organic fiber materials | |
| DE2234468C3 (en) | Basic azo dyes, their production and their use for dyeing preferably acid-modified synthetic fibers | |
| DE2013791A1 (en) | Yellow basic hydrazone dyes for polyacry-lonitrile etc | |
| DE2039492A1 (en) | Cationic dyes | |
| DE2341289A1 (en) | BASIC COLORS, METHOD FOR MANUFACTURING AND USING them | |
| DE2503098A1 (en) | Cationic methine dyes - comprising 2-(substd. anilino-vinyl)-1-substd-indoleninium salts | |
| DE2408044A1 (en) | Basic dyes of naphthoylene arylimidazole series - for mordanted cellulose, silk, leather, acetate or acid-modified synthetic fibres | |
| DE2211958A1 (en) | BASIC COLORS | |
| DE2064882C3 (en) | Basic dyes, processes for their production and their use for dyeing and printing polyacrylonitriles, polyesters, polyamides, leather and tannin cotton and for producing writing fluids and printing pastes | |
| DE2064881C3 (en) | Indolenine dyes, processes for their production and their use for dyeing and printing polymers and copolymers, leather, tannin cotton and for producing writing fluids and printing pastes | |
| DE1903058C (en) | Process for the production of basic azo dyes and their use for colors and printing | |
| DE3503705A1 (en) | Cationic methine compounds | |
| AT244284B (en) | Process for improving the white appearance of polymeric material | |
| CH625822A5 (en) | Process for preparing hydrazone dyes | |
| DE1103485B (en) | Process for the preparation of basic styryl dyes |