BE626052A - - Google Patents

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Publication number

BE626052A

BE626052A BE626052DA BE626052A BE 626052 A BE626052 A BE 626052A BE 626052D A BE626052D A BE 626052DA BE 626052 A BE626052 A BE 626052A

Authority

BE

Belgium

Prior art keywords

acid

carbon atoms

parts

formula

dye

Prior art date

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• 239000000975 dye Substances 0.000 claims description 35
• 239000002253 acid Substances 0.000 claims description 34
• 238000005859 coupling reaction Methods 0.000 claims description 17
• 230000008878 coupling Effects 0.000 claims description 16
• 238000010168 coupling process Methods 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• PWKULOLAYWPTES-UHFFFAOYSA-N Nc1cccc(c1Oc1ccccc1)S(O)(=O)=O Chemical compound Nc1cccc(c1Oc1ccccc1)S(O)(=O)=O PWKULOLAYWPTES-UHFFFAOYSA-N 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• 239000002657 fibrous material Substances 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 3
• 239000003795 chemical substances by application Substances 0.000 claims description 2
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
• 230000001747 exhibiting effect Effects 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• 239000000243 solution Substances 0.000 description 11
• 210000002268 wool Anatomy 0.000 description 8
• -1 bromine or Chemical class 0.000 description 7
• 150000002430 hydrocarbons Chemical group 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• 239000011780 sodium chloride Substances 0.000 description 6
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
• 159000000000 sodium salts Chemical class 0.000 description 6
• 239000000203 mixture Substances 0.000 description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
• 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 4
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
• 229920002647 polyamide Polymers 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• 239000001632 sodium acetate Substances 0.000 description 4
• 235000017281 sodium acetate Nutrition 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 230000027326 copulation Effects 0.000 description 3
• 238000006193 diazotization reaction Methods 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• 235000010288 sodium nitrite Nutrition 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
• 125000003118 aryl group Chemical group 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
• 235000014113 dietary fatty acids Nutrition 0.000 description 2
• 239000000194 fatty acid Substances 0.000 description 2
• 229930195729 fatty acid Natural products 0.000 description 2
• 150000004665 fatty acids Chemical class 0.000 description 2
• 230000007935 neutral effect Effects 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• 239000013535 sea water Substances 0.000 description 2
• MYPXYQMABPTFFN-UHFFFAOYSA-N 4-phenoxybenzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1OC1=CC=CC=C1 MYPXYQMABPTFFN-UHFFFAOYSA-N 0.000 description 1
• OWJIQELXSVMLJG-UHFFFAOYSA-N 5-(benzylamino)-6-(2-chloroacetyl)-4-hydroxynaphthalene-2-sulfonic acid Chemical compound ClCC(=O)C1=C(C2=C(C=C(C=C2C=C1)S(=O)(=O)O)O)NCC1=CC=CC=C1 OWJIQELXSVMLJG-UHFFFAOYSA-N 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
• SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• 101100009427 Mus musculus Dexi gene Proteins 0.000 description 1
• 239000004677 Nylon Substances 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 239000004952 Polyamide Substances 0.000 description 1
• 229920000388 Polyphosphate Polymers 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 150000001447 alkali salts Chemical class 0.000 description 1
• 125000002947 alkylene group Chemical group 0.000 description 1
• 229940024606 amino acid Drugs 0.000 description 1
• 125000005228 aryl sulfonate group Chemical group 0.000 description 1
• POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 125000000753 cycloalkyl group Chemical group 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000002704 decyl 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])* 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
• 238000010410 dusting Methods 0.000 description 1
• 238000004043 dyeing Methods 0.000 description 1
• WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000000835 fiber Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 229910052736 halogen Inorganic materials 0.000 description 1
• 150000002367 halogens Chemical class 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
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 239000010985 leather Substances 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
• 125000001421 myristyl 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])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 229920001778 nylon Polymers 0.000 description 1
• 125000002347 octyl 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])[H] 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• 235000021317 phosphate Nutrition 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 235000021178 picnic Nutrition 0.000 description 1
• 238000006068 polycondensation reaction Methods 0.000 description 1
• 239000001205 polyphosphate Substances 0.000 description 1
• 235000011176 polyphosphates Nutrition 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 239000012266 salt solution Substances 0.000 description 1
• RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
• 229960005369 scarlet red Drugs 0.000 description 1
• FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
• 125000003944 tolyl group Chemical group 0.000 description 1
• 230000001256 tonic effect Effects 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1