BE491044A - - Google Patents

Info

Publication number

BE491044A

BE491044A BE491044DA BE491044A BE 491044 A BE491044 A BE 491044A BE 491044D A BE491044D A BE 491044DA BE 491044 A BE491044 A BE 491044A

Authority

BE

Belgium

Prior art keywords

dyes

benzophenone

indolyl

radical

hydrogen

Prior art date

Links

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• 239000000975 dye Substances 0.000 description 25
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Substances 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• 239000007859 condensation product Substances 0.000 description 6
• RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 125000001424 substituent group Chemical group 0.000 description 6
• 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 5
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
• 239000012965 benzophenone Substances 0.000 description 5
• 150000001875 compounds Chemical class 0.000 description 5
• 230000007935 neutral effect Effects 0.000 description 5
• IRBQXLPYJHWQTM-UHFFFAOYSA-N 2-benzhydryl-1h-indole Chemical class N1C2=CC=CC=C2C=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 IRBQXLPYJHWQTM-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 239000000835 fiber Substances 0.000 description 4
• 229910052739 hydrogen Inorganic materials 0.000 description 4
• 239000001257 hydrogen Substances 0.000 description 4
• 238000002844 melting Methods 0.000 description 4
• 230000008018 melting Effects 0.000 description 4
• 238000000034 method Methods 0.000 description 4
• BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 4
• 210000002268 wool Anatomy 0.000 description 4
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
• KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 239000004215 Carbon black (E152) Substances 0.000 description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
• 125000000217 alkyl group Chemical group 0.000 description 3
• 238000009833 condensation Methods 0.000 description 3
• 230000005494 condensation Effects 0.000 description 3
• 229930195733 hydrocarbon Natural products 0.000 description 3
• 239000013067 intermediate product Substances 0.000 description 3
• 238000001556 precipitation Methods 0.000 description 3
• 238000002360 preparation method Methods 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 239000007787 solid Substances 0.000 description 3
• IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
• YKINVWJZGOCCRS-UHFFFAOYSA-N ClC1=CC=C(C(=O)C2=CC=C(C=C2)Cl)C=C1.[Na] Chemical compound ClC1=CC=C(C(=O)C2=CC=C(C=C2)Cl)C=C1.[Na] YKINVWJZGOCCRS-UHFFFAOYSA-N 0.000 description 2
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 125000001931 aliphatic group Chemical group 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 150000004982 aromatic amines Chemical class 0.000 description 2
• -1 aromatic amino compound Chemical class 0.000 description 2
• 238000004090 dissolution Methods 0.000 description 2
• 229910052736 halogen Inorganic materials 0.000 description 2
• 150000002367 halogens Chemical class 0.000 description 2
• 150000002430 hydrocarbons Chemical class 0.000 description 2
• 229910052757 nitrogen Inorganic materials 0.000 description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 description 2
• RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
• 235000002639 sodium chloride Nutrition 0.000 description 2
• 210000004243 sweat Anatomy 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• 239000011592 zinc chloride Substances 0.000 description 2
• 235000005074 zinc chloride Nutrition 0.000 description 2
• GBUFJJGRMRCARE-UHFFFAOYSA-N 1-butoxycyclohexa-2,4-dien-1-amine Chemical compound C(CCC)OC1(N)CC=CC=C1 GBUFJJGRMRCARE-UHFFFAOYSA-N 0.000 description 1
• NSVNOSODIIDWKL-UHFFFAOYSA-N 1-cyclohexyl-2-methylindole Chemical compound C1(CCCCC1)N1C(=CC2=CC=CC=C12)C NSVNOSODIIDWKL-UHFFFAOYSA-N 0.000 description 1
• MXALRLXMXCYNGF-UHFFFAOYSA-N 1h-indole-2-sulfonic acid Chemical class C1=CC=C2NC(S(=O)(=O)O)=CC2=C1 MXALRLXMXCYNGF-UHFFFAOYSA-N 0.000 description 1
• CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
• CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
• LNEVUNYUJNORRV-UHFFFAOYSA-N 2-chloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C(Cl)=C1 LNEVUNYUJNORRV-UHFFFAOYSA-N 0.000 description 1
• WEZAHYDFZNTGKE-UHFFFAOYSA-N 3-ethoxyaniline Chemical compound CCOC1=CC=CC(N)=C1 WEZAHYDFZNTGKE-UHFFFAOYSA-N 0.000 description 1
• QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
• WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 1
• 101100289061 Drosophila melanogaster lili gene Proteins 0.000 description 1
• AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
• 229960000583 acetic acid Drugs 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
• 150000008366 benzophenones Chemical class 0.000 description 1
• 239000001045 blue dye Substances 0.000 description 1
• 125000004432 carbon atom Chemical group C* 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 230000004927 fusion Effects 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 150000002431 hydrogen Chemical class 0.000 description 1
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
• 150000002790 naphthalenes Chemical class 0.000 description 1
• 229960001173 oxybenzone Drugs 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• 150000003142 primary aromatic amines Chemical group 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
• 239000013535 sea water Substances 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
• 238000006277 sulfonation reaction Methods 0.000 description 1
• 150000004992 toluidines Chemical class 0.000 description 1