DE1569742A1 - Aminodiphenyl-indolyl-methanfarbstoffe - Google Patents
Aminodiphenyl-indolyl-methanfarbstoffeInfo
- Publication number
- DE1569742A1 DE1569742A1 DE19661569742 DE1569742A DE1569742A1 DE 1569742 A1 DE1569742 A1 DE 1569742A1 DE 19661569742 DE19661569742 DE 19661569742 DE 1569742 A DE1569742 A DE 1569742A DE 1569742 A1 DE1569742 A1 DE 1569742A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- blue
- hydrogen
- methyl
- green
- 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.)
- Withdrawn
Links
- 239000000975 dye Substances 0.000 title claims description 42
- RSUXRBCOQDOFKV-UHFFFAOYSA-N 1h-indol-2-yl(diphenyl)methanamine Chemical compound C=1C2=CC=CC=C2NC=1C(N)(C=1C=CC=CC=1)C1=CC=CC=C1 RSUXRBCOQDOFKV-UHFFFAOYSA-N 0.000 title claims description 4
- -1 aralkyl radical Chemical class 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 150000002431 hydrogen Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 150000002475 indoles Chemical class 0.000 claims description 11
- 150000005840 aryl radicals Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 238000004043 dyeing Methods 0.000 claims description 9
- 239000000835 fiber Substances 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims description 6
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 claims description 6
- 125000005521 carbonamide group Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical class 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 125000002252 acyl group Chemical class 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical class 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000010985 leather Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- RLGAYEJPGHIHIB-UHFFFAOYSA-N 1h-indol-2-yl(phenyl)methanone Chemical class C=1C2=CC=CC=C2NC=1C(=O)C1=CC=CC=C1 RLGAYEJPGHIHIB-UHFFFAOYSA-N 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- MGQNMYSRDBFUIR-UHFFFAOYSA-N nitro cyanoformate Chemical compound [O-][N+](=O)OC(=O)C#N MGQNMYSRDBFUIR-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 229920005610 lignin Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229940090012 bentyl Drugs 0.000 claims 2
- 150000001733 carboxylic acid esters Chemical group 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- 230000004048 modification Effects 0.000 claims 2
- 238000012986 modification Methods 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- KYPOHTVBFVELTG-UHFFFAOYSA-N but-2-enedinitrile Chemical group N#CC=CC#N KYPOHTVBFVELTG-UHFFFAOYSA-N 0.000 claims 1
- 125000005518 carboxamido group Chemical class 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- BJMUOUXGBFNLSN-UHFFFAOYSA-N 1,2-dimethylindole Chemical compound C1=CC=C2N(C)C(C)=CC2=C1 BJMUOUXGBFNLSN-UHFFFAOYSA-N 0.000 description 41
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 36
- SFWZZSXCWQTORH-UHFFFAOYSA-N 1-methyl-2-phenylindole Chemical compound C=1C2=CC=CC=C2N(C)C=1C1=CC=CC=C1 SFWZZSXCWQTORH-UHFFFAOYSA-N 0.000 description 28
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 22
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 18
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 18
- 229920002239 polyacrylonitrile Polymers 0.000 description 17
- 244000172533 Viola sororia Species 0.000 description 15
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 14
- 229940024874 benzophenone Drugs 0.000 description 13
- 239000012965 benzophenone Substances 0.000 description 13
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 12
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 11
- IDLJKTNBZKSHIY-UHFFFAOYSA-N [4-(diethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CC=C1 IDLJKTNBZKSHIY-UHFFFAOYSA-N 0.000 description 11
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 235000021384 green leafy vegetables Nutrition 0.000 description 8
- 235000005074 zinc chloride Nutrition 0.000 description 7
- 239000011592 zinc chloride Substances 0.000 description 7
- RAKSXVONTIQCGY-UHFFFAOYSA-N 1-ethyl-2-phenylindole Chemical compound C=1C2=CC=CC=C2N(CC)C=1C1=CC=CC=C1 RAKSXVONTIQCGY-UHFFFAOYSA-N 0.000 description 6
- YZKUEVLTJBFTCA-UHFFFAOYSA-N 2-methyl-1H-indole 2-phenyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1.N1C2=CC=CC=C2C=C1C1=CC=CC=C1 YZKUEVLTJBFTCA-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 4
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical class C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 4
- WLJCLOGXBKKEFF-UHFFFAOYSA-N 1,2-dimethylindole 1-methyl-2-phenylindole Chemical compound C1=CC=C2N(C)C(C)=CC2=C1.C=1C2=CC=CC=C2N(C)C=1C1=CC=CC=C1 WLJCLOGXBKKEFF-UHFFFAOYSA-N 0.000 description 4
- MVQFXOFXNFCNAY-UHFFFAOYSA-N C1(=CC=CC=C1)CNC1=CC=C(C(=O)C2=C(C=CC=C2)Cl)C=C1 Chemical compound C1(=CC=CC=C1)CNC1=CC=C(C(=O)C2=C(C=CC=C2)Cl)C=C1 MVQFXOFXNFCNAY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- GRDGBWVSVMLKBV-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl GRDGBWVSVMLKBV-UHFFFAOYSA-N 0.000 description 3
- YPLXJJYRZRAVSY-UHFFFAOYSA-N (2-chlorophenyl)-[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CC=C1Cl YPLXJJYRZRAVSY-UHFFFAOYSA-N 0.000 description 3
- XGBZHVPAEOVEJN-UHFFFAOYSA-N (3-chlorophenyl)-[4-(dimethylamino)phenyl]methanone Chemical compound CN(C1=CC=C(C(=O)C2=CC(=CC=C2)Cl)C=C1)C XGBZHVPAEOVEJN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- JQDXUKCZXPSGBI-UHFFFAOYSA-N CCC(C=C1)=CC=C1C(C(C=CC=C1)=C1NCC(C=CC=C1)=C1Cl)=O Chemical compound CCC(C=C1)=CC=C1C(C(C=CC=C1)=C1NCC(C=CC=C1)=C1Cl)=O JQDXUKCZXPSGBI-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000005811 Viola adunca Nutrition 0.000 description 3
- 240000009038 Viola odorata Species 0.000 description 3
- 235000013487 Viola odorata Nutrition 0.000 description 3
- 235000002254 Viola papilionacea Nutrition 0.000 description 3
- QMGGUKZPEJFOKK-UHFFFAOYSA-N [2-chloro-4-(diethylamino)phenyl]-phenylmethanone Chemical compound ClC1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CC=C1 QMGGUKZPEJFOKK-UHFFFAOYSA-N 0.000 description 3
- WSLMBINPHIIBQL-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-(4-methylphenyl)methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(C)C=C1 WSLMBINPHIIBQL-UHFFFAOYSA-N 0.000 description 3
- BEUGBYXJXMVRFO-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1 BEUGBYXJXMVRFO-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000010979 ruby Substances 0.000 description 3
- 229910001750 ruby Inorganic materials 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- ABEVIHIQUUXDMS-UHFFFAOYSA-N (2-bromophenyl)-phenylmethanone Chemical compound BrC1=CC=CC=C1C(=O)C1=CC=CC=C1 ABEVIHIQUUXDMS-UHFFFAOYSA-N 0.000 description 2
- OJFZCPMENWLPRI-UHFFFAOYSA-N (2-ethylphenyl)-phenylmethanone Chemical compound CCC1=CC=CC=C1C(=O)C1=CC=CC=C1 OJFZCPMENWLPRI-UHFFFAOYSA-N 0.000 description 2
- UJHSIDUUJPTLDY-UHFFFAOYSA-N (2-nitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 UJHSIDUUJPTLDY-UHFFFAOYSA-N 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- PXWZXOKQTJPFDT-UHFFFAOYSA-N C(C)N(C1=CC=C(C(=O)C2=CC(=CC=C2)Cl)C=C1)CC Chemical compound C(C)N(C1=CC=C(C(=O)C2=CC(=CC=C2)Cl)C=C1)CC PXWZXOKQTJPFDT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920001864 tannin Polymers 0.000 description 2
- 235000018553 tannin Nutrition 0.000 description 2
- 239000001648 tannin Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NZSOIVBULOMONL-UHFFFAOYSA-N (1-ethyl-2-phenylindol-3-yl)-phenylmethanone Chemical compound C(C)N1C(=C(C2=CC=CC=C12)C(C1=CC=CC=C1)=O)C1=CC=CC=C1 NZSOIVBULOMONL-UHFFFAOYSA-N 0.000 description 1
- RLUFBDIRFJGKLY-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Cl RLUFBDIRFJGKLY-UHFFFAOYSA-N 0.000 description 1
- PKSVTEMCGNQIMD-UHFFFAOYSA-N (2-aminophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1Cl PKSVTEMCGNQIMD-UHFFFAOYSA-N 0.000 description 1
- COMTXRHVBLIIOW-UHFFFAOYSA-N (2-aminophenyl)-(3-chlorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC(Cl)=C1 COMTXRHVBLIIOW-UHFFFAOYSA-N 0.000 description 1
- ODIZFLBVAACVBX-UHFFFAOYSA-N (2-chlorophenyl)-(1,2-dimethylindol-3-yl)methanone Chemical compound CN1C(=C(C2=CC=CC=C12)C(C1=C(C=CC=C1)Cl)=O)C ODIZFLBVAACVBX-UHFFFAOYSA-N 0.000 description 1
- UEDUMQUYPBSPCR-UHFFFAOYSA-N (3-amino-2-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Cl UEDUMQUYPBSPCR-UHFFFAOYSA-N 0.000 description 1
- NHTALIXIQROOBT-UHFFFAOYSA-N (3-amino-2-methylphenyl)-phenylmethanone Chemical compound CC1=C(N)C=CC=C1C(=O)C1=CC=CC=C1 NHTALIXIQROOBT-UHFFFAOYSA-N 0.000 description 1
- FVXMNNUNMZQSFG-UHFFFAOYSA-N (3-chlorophenyl)-(1-methyl-2-phenylindol-3-yl)methanone Chemical compound CN1C(=C(C2=CC=CC=C12)C(C1=CC(=CC=C1)Cl)=O)C1=CC=CC=C1 FVXMNNUNMZQSFG-UHFFFAOYSA-N 0.000 description 1
- BMDLVWKJJZQIBY-UHFFFAOYSA-N (5-chloro-1,2-dimethylindol-3-yl)-phenylmethanone Chemical compound CN1C(=C(C2=CC(=CC=C12)Cl)C(C1=CC=CC=C1)=O)C BMDLVWKJJZQIBY-UHFFFAOYSA-N 0.000 description 1
- AEMGLFFJJFUNEV-UHFFFAOYSA-N (5-chloro-1h-indol-3-yl)-phenylmethanone Chemical compound C12=CC(Cl)=CC=C2NC=C1C(=O)C1=CC=CC=C1 AEMGLFFJJFUNEV-UHFFFAOYSA-N 0.000 description 1
- QEOSOLXDPRSDKG-UHFFFAOYSA-N 1,2,5-trimethylindole Chemical compound CC1=CC=C2N(C)C(C)=CC2=C1 QEOSOLXDPRSDKG-UHFFFAOYSA-N 0.000 description 1
- DDDWOOPXAXNEHE-UHFFFAOYSA-N 1,4,7-trimethyl-2-phenylindole Chemical compound CN1C(=CC2=C(C=CC(=C12)C)C)C1=CC=CC=C1 DDDWOOPXAXNEHE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HULGQFJADCYBQY-UHFFFAOYSA-N 1,7-dimethyl-2-phenylindole Chemical compound CN1C=2C(C)=CC=CC=2C=C1C1=CC=CC=C1 HULGQFJADCYBQY-UHFFFAOYSA-N 0.000 description 1
- DPNOTFHCABPNQH-UHFFFAOYSA-N 1-benzyl-2-methylindole Chemical compound CC1=CC2=CC=CC=C2N1CC1=CC=CC=C1 DPNOTFHCABPNQH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/62—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an ethylenimino or N—acylated ethylenimino group or a —CO—NH—CH2—CH2—X group, wherein X is a halogen atom, a quaternary ammonium group or O—acyl and acyl is derived from an organic or inorganic acid, or a beta—substituted ethylamine group
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coloring (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0049866 | 1966-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1569742A1 true DE1569742A1 (de) | 1970-07-30 |
Family
ID=7103338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661569742 Withdrawn DE1569742A1 (de) | 1966-08-03 | 1966-08-03 | Aminodiphenyl-indolyl-methanfarbstoffe |
Country Status (11)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7211117B2 (en) | 2002-12-30 | 2007-05-01 | L'oreal S.A. | Composition for dyeing keratin fibers comprising at least one dye chosen from monoheteroyldiarylmethane direct dyes and the leuco precursors thereof and dyeing method using it |
| US7217297B2 (en) | 2002-12-30 | 2007-05-15 | L'oreal S.A. | Composition for dyeing keratin fibers comprising a defined diheteroylarylmethane direct dye or a leuco precursor of this dye and dyeing method using it |
| US7211118B2 (en) | 2002-12-30 | 2007-05-01 | L'oreal S.A. | Composition for dyeing keratin fibers comprising a defined triheteroylmethane direct dye or leuco precursor of this dye and dyeing method using it |
-
1966
- 1966-08-03 DE DE19661569742 patent/DE1569742A1/de not_active Withdrawn
-
1967
- 1967-07-10 CH CH978467A patent/CH522021A/de not_active IP Right Cessation
- 1967-07-11 IL IL2829667A patent/IL28296A/xx unknown
- 1967-07-31 NL NL6710576A patent/NL6710576A/xx unknown
- 1967-07-31 AT AT62268A patent/AT267713B/de active
- 1967-07-31 AT AT709067A patent/AT267712B/de active
- 1967-08-01 GB GB3532367A patent/GB1139407A/en not_active Expired
- 1967-08-02 SE SE1106267A patent/SE336032B/xx unknown
- 1967-08-03 NO NO169261A patent/NO123135B/no unknown
- 1967-08-03 FR FR116822A patent/FR1533624A/fr not_active Expired
- 1967-08-03 BE BE702240D patent/BE702240A/xx unknown
- 1967-11-10 ES ES346983A patent/ES346983A1/es not_active Expired
- 1967-11-10 ES ES346984A patent/ES346984A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES346984A1 (es) | 1969-01-16 |
| ES346983A1 (es) | 1969-01-16 |
| BE702240A (enrdf_load_stackoverflow) | 1968-02-05 |
| NL6710576A (enrdf_load_stackoverflow) | 1968-02-05 |
| AT267713B (de) | 1969-01-10 |
| FR1533624A (fr) | 1968-07-19 |
| GB1139407A (en) | 1969-01-08 |
| IL28296A (en) | 1971-01-28 |
| AT267712B (de) | 1969-01-10 |
| CH522021A (de) | 1972-04-30 |
| SE336032B (enrdf_load_stackoverflow) | 1971-06-21 |
| NO123135B (enrdf_load_stackoverflow) | 1971-10-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |