NO123135B - - Google Patents
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- NO123135B NO123135B NO169261A NO16926167A NO123135B NO 123135 B NO123135 B NO 123135B NO 169261 A NO169261 A NO 169261A NO 16926167 A NO16926167 A NO 16926167A NO 123135 B NO123135 B NO 123135B
- Authority
- NO
- Norway
- Prior art keywords
- parts
- methyl
- phenyl
- weight
- dyes
- Prior art date
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- 239000000975 dye Substances 0.000 claims abstract 42
- -1 aralkyl radical Chemical class 0.000 claims abstract 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 16
- 239000001257 hydrogen Substances 0.000 claims abstract 16
- 125000003118 aryl group Chemical group 0.000 claims abstract 11
- 238000004043 dyeing Methods 0.000 claims abstract 11
- 239000002253 acid Substances 0.000 claims abstract 10
- 125000003545 alkoxy group Chemical class 0.000 claims abstract 10
- 150000002431 hydrogen Chemical class 0.000 claims abstract 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 7
- 239000000460 chlorine Substances 0.000 claims abstract 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000000129 anionic group Chemical group 0.000 claims abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract 6
- 125000005521 carbonamide group Chemical class 0.000 claims abstract 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 6
- 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 claims abstract 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract 5
- 239000000463 material Substances 0.000 claims abstract 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 4
- 239000010985 leather Substances 0.000 claims abstract 4
- 229920000728 polyester Polymers 0.000 claims abstract 4
- 229920000642 polymer Polymers 0.000 claims abstract 4
- 125000001424 substituent group Chemical group 0.000 claims abstract 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract 3
- 229920000742 Cotton Polymers 0.000 claims abstract 3
- 229920001971 elastomer Polymers 0.000 claims abstract 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims abstract 3
- 239000012530 fluid Substances 0.000 claims abstract 3
- 229920005610 lignin Polymers 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 3
- FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002252 acyl group Chemical class 0.000 claims abstract 2
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- 125000004390 alkyl sulfonyl group Chemical class 0.000 claims abstract 2
- 125000004391 aryl sulfonyl group Chemical class 0.000 claims abstract 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims abstract 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims abstract 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims abstract 2
- MGQNMYSRDBFUIR-UHFFFAOYSA-N nitro cyanoformate Chemical compound [O-][N+](=O)OC(=O)C#N MGQNMYSRDBFUIR-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims abstract 2
- 125000003944 tolyl group Chemical group 0.000 claims abstract 2
- 150000003673 urethanes Chemical class 0.000 claims abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 1
- 239000000976 ink Substances 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 17
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 14
- 239000000835 fiber Substances 0.000 abstract 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 12
- 239000000243 solution Substances 0.000 abstract 12
- 238000000034 method Methods 0.000 abstract 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 11
- 150000002475 indoles Chemical class 0.000 abstract 8
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 7
- 235000005074 zinc chloride Nutrition 0.000 abstract 7
- 239000011592 zinc chloride Substances 0.000 abstract 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 6
- 229960000583 acetic acid Drugs 0.000 abstract 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 6
- 239000003795 chemical substances by application Substances 0.000 abstract 6
- 238000002360 preparation method Methods 0.000 abstract 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 6
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical class C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 abstract 5
- 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 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- 230000002378 acidificating effect Effects 0.000 abstract 4
- 229940054051 antipsychotic indole derivative Drugs 0.000 abstract 4
- 150000004982 aromatic amines Chemical class 0.000 abstract 4
- 150000005840 aryl radicals Chemical class 0.000 abstract 4
- 238000009835 boiling Methods 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 229920000151 polyglycol Polymers 0.000 abstract 4
- 239000010695 polyglycol Substances 0.000 abstract 4
- 239000001632 sodium acetate Substances 0.000 abstract 4
- 235000017281 sodium acetate Nutrition 0.000 abstract 4
- BJMUOUXGBFNLSN-UHFFFAOYSA-N 1,2-dimethylindole Chemical compound C1=CC=C2N(C)C(C)=CC2=C1 BJMUOUXGBFNLSN-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 239000012943 hotmelt Substances 0.000 abstract 3
- 238000003756 stirring Methods 0.000 abstract 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 3
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 abstract 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 2
- 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 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 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 abstract 2
- 238000001556 precipitation Methods 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 235000002639 sodium chloride Nutrition 0.000 abstract 2
- 239000011780 sodium chloride Substances 0.000 abstract 2
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 2
- 235000011152 sodium sulphate Nutrition 0.000 abstract 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 abstract 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 abstract 2
- IMHIUKAZHVRWLI-UHFFFAOYSA-N (1,2-dimethylindol-3-yl)-(4-methylphenyl)methanone Chemical compound CN1C(=C(C2=CC=CC=C12)C(C1=CC=C(C=C1)C)=O)C IMHIUKAZHVRWLI-UHFFFAOYSA-N 0.000 abstract 1
- YNRUHEWLGHUHIT-UHFFFAOYSA-N (1,5-dimethyl-2-phenylindol-3-yl)-phenylmethanone Chemical compound CN1C(=C(C2=CC(=CC=C12)C)C(C1=CC=CC=C1)=O)C1=CC=CC=C1 YNRUHEWLGHUHIT-UHFFFAOYSA-N 0.000 abstract 1
- HHPFBQIRSYDWAT-UHFFFAOYSA-N (1-benzyl-2-methylindol-3-yl)-phenylmethanone Chemical compound C(C1=CC=CC=C1)N1C(=C(C2=CC=CC=C12)C(C1=CC=CC=C1)=O)C HHPFBQIRSYDWAT-UHFFFAOYSA-N 0.000 abstract 1
- DEZXVNYMIKCZQE-UHFFFAOYSA-N (1-ethyl-2-methylindol-3-yl)-phenylmethanone Chemical compound C(C)N1C(=C(C2=CC=CC=C12)C(C1=CC=CC=C1)=O)C DEZXVNYMIKCZQE-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- QZJDCNMYGQGWNP-UHFFFAOYSA-N (1-methyl-2-phenylindol-3-yl)-phenylmethanone Chemical compound C12=CC=CC=C2N(C)C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC=C1 QZJDCNMYGQGWNP-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- GMGOAAYOUBDRGR-UHFFFAOYSA-N (2-chlorophenyl)-(1-ethyl-2-phenylindol-3-yl)methanone Chemical compound C(C)N1C(=C(C2=CC=CC=C12)C(C1=C(C=CC=C1)Cl)=O)C1=CC=CC=C1 GMGOAAYOUBDRGR-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- XIKKSSZCWXLPHW-UHFFFAOYSA-N (4-methylphenyl)-(1-methyl-2-phenylindol-3-yl)methanone Chemical compound CN1C(=C(C2=CC=CC=C12)C(C1=CC=C(C=C1)C)=O)C1=CC=CC=C1 XIKKSSZCWXLPHW-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- QEOSOLXDPRSDKG-UHFFFAOYSA-N 1,2,5-trimethylindole Chemical compound CC1=CC=C2N(C)C(C)=CC2=C1 QEOSOLXDPRSDKG-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- YSGYUYIEJJVBOV-UHFFFAOYSA-N 1,5-dimethyl-2-phenylindole Chemical compound C=1C2=CC(C)=CC=C2N(C)C=1C1=CC=CC=C1 YSGYUYIEJJVBOV-UHFFFAOYSA-N 0.000 abstract 1
- DPNOTFHCABPNQH-UHFFFAOYSA-N 1-benzyl-2-methylindole Chemical compound CC1=CC2=CC=CC=C2N1CC1=CC=CC=C1 DPNOTFHCABPNQH-UHFFFAOYSA-N 0.000 abstract 1
- ZJCWHQUDJBYRBY-UHFFFAOYSA-N 1-ethyl-2,5-dimethylindole Chemical compound CC1=CC=C2N(CC)C(C)=CC2=C1 ZJCWHQUDJBYRBY-UHFFFAOYSA-N 0.000 abstract 1
- XMOWAIVXKJWQBJ-UHFFFAOYSA-N 1-ethyl-2-methylindole Chemical compound C1=CC=C2N(CC)C(C)=CC2=C1 XMOWAIVXKJWQBJ-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- JPPRLJRKQCFSJF-UHFFFAOYSA-N 1-ethyl-5-methyl-2-phenylindole Chemical compound C=1C2=CC(C)=CC=C2N(CC)C=1C1=CC=CC=C1 JPPRLJRKQCFSJF-UHFFFAOYSA-N 0.000 abstract 1
- ZFLFWZRPMDXJCW-UHFFFAOYSA-N 2,5-dimethyl-1h-indole Chemical compound CC1=CC=C2NC(C)=CC2=C1 ZFLFWZRPMDXJCW-UHFFFAOYSA-N 0.000 abstract 1
- VQMXBVLBBNJCCF-UHFFFAOYSA-N 2,6-dichloro-n-phenylbenzamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC1=CC=CC=C1 VQMXBVLBBNJCCF-UHFFFAOYSA-N 0.000 abstract 1
- UCVKTHKIFMYJKD-UHFFFAOYSA-N 2-(2-methyl-1h-indol-3-yl)propanenitrile Chemical compound C1=CC=C2C(C(C#N)C)=C(C)NC2=C1 UCVKTHKIFMYJKD-UHFFFAOYSA-N 0.000 abstract 1
- WQWUNEXIEANIEA-UHFFFAOYSA-N 2-(2-phenyl-1h-indol-3-yl)propanenitrile Chemical compound N1C2=CC=CC=C2C(C(C#N)C)=C1C1=CC=CC=C1 WQWUNEXIEANIEA-UHFFFAOYSA-N 0.000 abstract 1
- UMEJEJTXMPATDO-UHFFFAOYSA-N 2-(3-benzoyl-2-methyl-1H-indol-4-yl)propanenitrile Chemical compound C(#N)C(C)C1=C2C(=C(NC2=CC=C1)C)C(C1=CC=CC=C1)=O UMEJEJTXMPATDO-UHFFFAOYSA-N 0.000 abstract 1
- PHOKVSZAUQPQRB-UHFFFAOYSA-N 2-(3-benzoyl-2-phenyl-1H-indol-4-yl)propanenitrile Chemical compound C(#N)C(C)C1=C2C(=C(NC2=CC=C1)C1=CC=CC=C1)C(C1=CC=CC=C1)=O PHOKVSZAUQPQRB-UHFFFAOYSA-N 0.000 abstract 1
- IRBQXLPYJHWQTM-UHFFFAOYSA-N 2-benzhydryl-1h-indole Chemical compound N1C2=CC=CC=C2C=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 IRBQXLPYJHWQTM-UHFFFAOYSA-N 0.000 abstract 1
- AXQVIWHAEYLGLO-UHFFFAOYSA-N 2-chloro-n-phenylbenzamide Chemical compound ClC1=CC=CC=C1C(=O)NC1=CC=CC=C1 AXQVIWHAEYLGLO-UHFFFAOYSA-N 0.000 abstract 1
- RZGWIZIPFZROQZ-UHFFFAOYSA-N 2-methoxy-n-phenylbenzamide Chemical compound COC1=CC=CC=C1C(=O)NC1=CC=CC=C1 RZGWIZIPFZROQZ-UHFFFAOYSA-N 0.000 abstract 1
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 abstract 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- OMYONBGWFUJAOW-UHFFFAOYSA-N 3-(n-phenylanilino)propanenitrile Chemical compound C=1C=CC=CC=1N(CCC#N)C1=CC=CC=C1 OMYONBGWFUJAOW-UHFFFAOYSA-N 0.000 abstract 1
- QDIUKUHOHYCIRM-UHFFFAOYSA-N 3-chloro-n-phenylbenzamide Chemical compound ClC1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1 QDIUKUHOHYCIRM-UHFFFAOYSA-N 0.000 abstract 1
- DUSYVXRZSXLXRH-UHFFFAOYSA-N 3-methyl-n-phenylbenzamide Chemical compound CC1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1 DUSYVXRZSXLXRH-UHFFFAOYSA-N 0.000 abstract 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 abstract 1
- GXTYWFWNCDJBDP-UHFFFAOYSA-N 4-ethoxy-n-methyl-n-phenylaniline Chemical compound C1=CC(OCC)=CC=C1N(C)C1=CC=CC=C1 GXTYWFWNCDJBDP-UHFFFAOYSA-N 0.000 abstract 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 abstract 1
- PQEOPHYIUYAVDQ-UHFFFAOYSA-N 4-methyl-n-phenylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC1=CC=CC=C1 PQEOPHYIUYAVDQ-UHFFFAOYSA-N 0.000 abstract 1
- CBJYDLXZVJGACV-UHFFFAOYSA-N 5-chloro-1,2-dimethylindole Chemical compound ClC1=CC=C2N(C)C(C)=CC2=C1 CBJYDLXZVJGACV-UHFFFAOYSA-N 0.000 abstract 1
- OSXFEOOBOWLYGP-UHFFFAOYSA-N 5-chloro-1-ethyl-2-methylindole Chemical compound ClC1=CC=C2N(CC)C(C)=CC2=C1 OSXFEOOBOWLYGP-UHFFFAOYSA-N 0.000 abstract 1
- DLBCVNORGVKPOS-UHFFFAOYSA-N 5-chloro-1-ethyl-2-phenylindole Chemical compound C=1C2=CC(Cl)=CC=C2N(CC)C=1C1=CC=CC=C1 DLBCVNORGVKPOS-UHFFFAOYSA-N 0.000 abstract 1
- YYNCJGFWLZBPNN-UHFFFAOYSA-N 5-chloro-1-methyl-2-phenylindole Chemical compound C=1C2=CC(Cl)=CC=C2N(C)C=1C1=CC=CC=C1 YYNCJGFWLZBPNN-UHFFFAOYSA-N 0.000 abstract 1
- WUVWAXJXPRYUME-UHFFFAOYSA-N 5-chloro-2-methyl-1h-indole Chemical compound ClC1=CC=C2NC(C)=CC2=C1 WUVWAXJXPRYUME-UHFFFAOYSA-N 0.000 abstract 1
- GQGZSWYJDNGSBE-UHFFFAOYSA-N 5-chloro-2-phenyl-1h-indole Chemical compound C=1C2=CC(Cl)=CC=C2NC=1C1=CC=CC=C1 GQGZSWYJDNGSBE-UHFFFAOYSA-N 0.000 abstract 1
- JPFTUUXPCFNLIX-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-indole Chemical compound C=1C2=CC(C)=CC=C2NC=1C1=CC=CC=C1 JPFTUUXPCFNLIX-UHFFFAOYSA-N 0.000 abstract 1
- WHOVJSPCXWJPBL-UHFFFAOYSA-N 6-methyl-2-phenyl-1h-indole Chemical compound N1C2=CC(C)=CC=C2C=C1C1=CC=CC=C1 WHOVJSPCXWJPBL-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 244000198134 Agave sisalana Species 0.000 abstract 1
- QWDGHSGOMHBPCX-UHFFFAOYSA-N CN1C(=C(C2=CC=CC=C12)C(C1=CC(=CC=C1)Cl)=O)C Chemical compound CN1C(=C(C2=CC=CC=C12)C(C1=CC(=CC=C1)Cl)=O)C QWDGHSGOMHBPCX-UHFFFAOYSA-N 0.000 abstract 1
- KCNIPOKANRMODZ-UHFFFAOYSA-N CN1C(=C(C2=CC=CC=C12)C(C1=CC=CC=C1)=O)C1=C(C=CC=C1)Cl Chemical compound CN1C(=C(C2=CC=CC=C12)C(C1=CC=CC=C1)=O)C1=C(C=CC=C1)Cl KCNIPOKANRMODZ-UHFFFAOYSA-N 0.000 abstract 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 abstract 1
- 244000060011 Cocos nucifera Species 0.000 abstract 1
- 235000013162 Cocos nucifera Nutrition 0.000 abstract 1
- 240000000491 Corchorus aestuans Species 0.000 abstract 1
- 235000011777 Corchorus aestuans Nutrition 0.000 abstract 1
- 235000010862 Corchorus capsularis Nutrition 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 abstract 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 abstract 1
- MZNCVTCEYXDDIS-UHFFFAOYSA-N Mebenil Chemical compound CC1=CC=CC=C1C(=O)NC1=CC=CC=C1 MZNCVTCEYXDDIS-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- PBEXYSJQJJCLEE-UHFFFAOYSA-N [2-(n-methylanilino)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1N(C)C1=CC=CC=C1 PBEXYSJQJJCLEE-UHFFFAOYSA-N 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 230000002411 adverse Effects 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 229940077388 benzenesulfonate Drugs 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 abstract 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 239000012267 brine Substances 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 235000019646 color tone Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 abstract 1
- YMMOMVVOOHRPOM-UHFFFAOYSA-N n,n-dichloro-2-ethylaniline Chemical compound CCC1=CC=CC=C1N(Cl)Cl YMMOMVVOOHRPOM-UHFFFAOYSA-N 0.000 abstract 1
- FUNVESSXWQPDQU-UHFFFAOYSA-N n-(2,5-dichlorophenyl)benzamide Chemical compound ClC1=CC=C(Cl)C(NC(=O)C=2C=CC=CC=2)=C1 FUNVESSXWQPDQU-UHFFFAOYSA-N 0.000 abstract 1
- KYTLVUBCXILIQO-UHFFFAOYSA-N n-(2-chloroethyl)-n-methylaniline Chemical compound ClCCN(C)C1=CC=CC=C1 KYTLVUBCXILIQO-UHFFFAOYSA-N 0.000 abstract 1
- HSZCJVZRHXPCIA-UHFFFAOYSA-N n-benzyl-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 abstract 1
- LXZGVFCKZRHKMU-UHFFFAOYSA-N n-benzyl-n-methylaniline Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC=C1 LXZGVFCKZRHKMU-UHFFFAOYSA-N 0.000 abstract 1
- ITMSSZATZARZCA-UHFFFAOYSA-N n-ethyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CC)C1=CC=CC=C1 ITMSSZATZARZCA-UHFFFAOYSA-N 0.000 abstract 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 1
- BFRAIKXHUTZOOQ-UHFFFAOYSA-N phenyl-(1,2,5-trimethylindol-3-yl)methanone Chemical compound CN1C(=C(C2=CC(=CC=C12)C)C(C1=CC=CC=C1)=O)C BFRAIKXHUTZOOQ-UHFFFAOYSA-N 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000002689 soil Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000010186 staining Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000000859 sublimation Methods 0.000 abstract 1
- 230000008022 sublimation Effects 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 229920001864 tannin Polymers 0.000 abstract 1
- 235000018553 tannin Nutrition 0.000 abstract 1
- 239000001648 tannin Substances 0.000 abstract 1
- 229940095064 tartrate Drugs 0.000 abstract 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Indole Compounds (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0049866 | 1966-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123135B true NO123135B (enrdf_load_stackoverflow) | 1971-10-04 |
Family
ID=7103338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO169261A NO123135B (enrdf_load_stackoverflow) | 1966-08-03 | 1967-08-03 |
Country Status (11)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 AT AT709067A patent/AT267712B/de active
- 1967-07-31 AT AT62268A patent/AT267713B/de active
- 1967-07-31 NL NL6710576A patent/NL6710576A/xx unknown
- 1967-08-01 GB GB3532367A patent/GB1139407A/en not_active Expired
- 1967-08-02 SE SE1106267A patent/SE336032B/xx unknown
- 1967-08-03 BE BE702240D patent/BE702240A/xx unknown
- 1967-08-03 FR FR116822A patent/FR1533624A/fr not_active Expired
- 1967-08-03 NO NO169261A patent/NO123135B/no unknown
- 1967-11-10 ES ES346984A patent/ES346984A1/es not_active Expired
- 1967-11-10 ES ES346983A patent/ES346983A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1569742A1 (de) | 1970-07-30 |
| NL6710576A (enrdf_load_stackoverflow) | 1968-02-05 |
| FR1533624A (fr) | 1968-07-19 |
| GB1139407A (en) | 1969-01-08 |
| SE336032B (enrdf_load_stackoverflow) | 1971-06-21 |
| CH522021A (de) | 1972-04-30 |
| IL28296A (en) | 1971-01-28 |
| AT267713B (de) | 1969-01-10 |
| ES346983A1 (es) | 1969-01-16 |
| AT267712B (de) | 1969-01-10 |
| ES346984A1 (es) | 1969-01-16 |
| BE702240A (enrdf_load_stackoverflow) | 1968-02-05 |
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