BE560839A

BE560839A -

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Publication number: BE560839A
Authority: BE; Belgium
Prior art keywords: sulfonic acid; group; hydrogen atom; carboxylic acid; formula
Prior art date

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English (en)

French (fr)

Publication of BE560839A publication Critical patent/BE560839A/fr

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239000000975 dye Substances 0.000 claims description 43
239000002253 acid Substances 0.000 claims description 18
238000000034 method Methods 0.000 claims description 15
125000000542 sulfonic acid group Chemical group 0.000 claims description 14
-1 aminoazo compound Chemical class 0.000 claims description 13
125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 12
125000002843 carboxylic acid group Chemical group 0.000 claims description 10
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 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atoms Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
150000004982 aromatic amines Chemical class 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims 1
SQOYRTHDGYBUSX-UHFFFAOYSA-N 3-amino-5-chloro-4-methoxybenzenesulfonic acid Chemical compound COC1=C(N)C=C(S(O)(=O)=O)C=C1Cl SQOYRTHDGYBUSX-UHFFFAOYSA-N 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
230000001808 coupling Effects 0.000 description 14
238000010168 coupling process Methods 0.000 description 13
238000005859 coupling reaction Methods 0.000 description 13
239000011780 sodium chloride Substances 0.000 description 11
150000003839 salts Chemical class 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 9
MGNCLNQXLYJVJD-UHFFFAOYSA-N Cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 8
239000000470 constituent Substances 0.000 description 8
239000000463 material Substances 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
239000007787 solid Substances 0.000 description 8
229920000297 Rayon Polymers 0.000 description 7
239000004753 textile Substances 0.000 description 7
229920000742 Cotton Polymers 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
GNSKLFRGEWLPPA-UHFFFAOYSA-M Monopotassium phosphate Chemical class [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical class [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 5
150000003142 primary aromatic amines Chemical class 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
150000008049 diazo compounds Chemical class 0.000 description 4
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
QXNVGIXVLWOKEQ-UHFFFAOYSA-N disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
239000001187 sodium carbonate Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
LWIHDJKSTIGBAC-UHFFFAOYSA-K Tripotassium phosphate Chemical class [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 3
210000002268 Wool Anatomy 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000000987 azo dye Substances 0.000 description 3
239000006172 buffering agent Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
239000004744 fabric Substances 0.000 description 3
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
239000002516 radical scavenger Substances 0.000 description 3
SXQCTESRRZBPHJ-UHFFFAOYSA-M sodium;4-[3-(diethylamino)-6-diethylazaniumylidenexanthen-9-yl]benzene-1,3-disulfonate Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 3
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-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
LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 2
HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000004442 acylamino group Chemical group 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000004043 dyeing Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
235000019796 monopotassium phosphate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
HFBYLYCMISIEMM-FFHNEAJVSA-N (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid Chemical compound OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC HFBYLYCMISIEMM-FFHNEAJVSA-N 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
FJHGMUDVUAXUEK-UHFFFAOYSA-N 2-amino-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(N)=C1 FJHGMUDVUAXUEK-UHFFFAOYSA-N 0.000 description 1
VYZCFAPUHSSYCC-UHFFFAOYSA-N 2-amino-5-chloro-4-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=C(S(O)(=O)=O)C=C1Cl VYZCFAPUHSSYCC-UHFFFAOYSA-N 0.000 description 1
DTNODBHGOLWROS-UHFFFAOYSA-N 3-amino-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1N DTNODBHGOLWROS-UHFFFAOYSA-N 0.000 description 1
JCYZYPAQHCTHGO-UHFFFAOYSA-N 3-amino-5-chloro-2-methoxybenzenesulfonic acid Chemical compound COC1=C(N)C=C(Cl)C=C1S(O)(=O)=O JCYZYPAQHCTHGO-UHFFFAOYSA-N 0.000 description 1
QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
240000003598 Fraxinus ornus Species 0.000 description 1
240000006669 Helianthus annuus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
125000003047 N-acetyl group Chemical group 0.000 description 1
NRZRRZAVMCAKEP-UHFFFAOYSA-N Naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
210000004940 Nucleus Anatomy 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical class COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229910006069 SO3H Inorganic materials 0.000 description 1
229940005550 Sodium alginate Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
230000002378 acidificating Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000000875 corresponding Effects 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000004994 m-toluidines Chemical class 0.000 description 1
239000010446 mirabilite Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000001264 neutralization Effects 0.000 description 1
150000004993 o-toluidines Chemical class 0.000 description 1
150000004995 p-toluidines Chemical class 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
VLYFRFHWUBBLRR-UHFFFAOYSA-L potassium;sodium;carbonate Chemical compound [Na+].[K+].[O-]C([O-])=O VLYFRFHWUBBLRR-UHFFFAOYSA-L 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000001044 red dye Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000008149 soap solution Substances 0.000 description 1
MSXHSNHNTORCAW-UHFFFAOYSA-M sodium 3,4,5,6-tetrahydroxyoxane-2-carboxylate Chemical compound [Na+].OC1OC(C([O-])=O)C(O)C(O)C1O MSXHSNHNTORCAW-UHFFFAOYSA-M 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical class [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
IGQFKZCLTLAWLO-HYNBPGMHSA-M sodium;4-[(2E)-2-(2-oxonaphthalen-1-ylidene)hydrazinyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N\N=C\1C2=CC=CC=C2C=CC/1=O IGQFKZCLTLAWLO-HYNBPGMHSA-M 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
BSUNTQCMCCQSQH-UHFFFAOYSA-N triazine Chemical compound C1=CN=NN=C1.C1=CN=NN=C1 BSUNTQCMCCQSQH-UHFFFAOYSA-N 0.000 description 1
235000019798 tripotassium phosphate Nutrition 0.000 description 1
SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1