BE552400A

BE552400A -

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Publication number: BE552400A
Authority: BE; Belgium
Prior art keywords: group; residue; azo; dyes; acid
Prior art date

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English (en)

French (fr)

Publication of BE552400A publication Critical patent/BE552400A/fr

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239000000975 dye Substances 0.000 claims description 51
239000002253 acid Substances 0.000 claims description 44
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 29
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
229910052751 metal Inorganic materials 0.000 claims description 16
239000002184 metal Substances 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
238000000034 method Methods 0.000 claims description 10
-1 polyazo Polymers 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 9
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000001624 naphthyl group Chemical group 0.000 claims description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
150000002739 metals Chemical class 0.000 claims description 6
230000001034 aminogenic effect Effects 0.000 claims description 5
229910052802 copper Inorganic materials 0.000 claims description 5
239000010949 copper Substances 0.000 claims description 5
229910052759 nickel Inorganic materials 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
150000001555 benzenes Chemical group 0.000 claims description 3
238000006193 diazotization reaction Methods 0.000 claims description 3
238000004043 dyeing Methods 0.000 claims description 3
239000000047 product Substances 0.000 claims description 3
230000007017 scission Effects 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims 2
125000006267 biphenyl group Chemical group 0.000 claims 2
GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 claims 1
150000004982 aromatic amines Chemical class 0.000 claims 1
238000010504 bond cleavage reaction Methods 0.000 claims 1
239000000470 constituent Substances 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
239000000243 solution Substances 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
150000008049 diazo compounds Chemical class 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
230000008878 coupling Effects 0.000 description 8
238000010168 coupling process Methods 0.000 description 8
238000005859 coupling reaction Methods 0.000 description 8
229920000742 Cotton Polymers 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
150000004699 copper complex Chemical class 0.000 description 5
238000001914 filtration Methods 0.000 description 5
235000010288 sodium nitrite Nutrition 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
239000000203 mixture Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
235000017281 sodium acetate Nutrition 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
238000001816 cooling Methods 0.000 description 3
230000027326 copulation Effects 0.000 description 3
239000002609 medium Substances 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
230000009466 transformation Effects 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
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 2
240000007817 Olea europaea Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
229910000365 copper sulfate Inorganic materials 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
239000001046 green dye Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000001465 metallisation Methods 0.000 description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
LHMILTWCGKFWAI-UHFFFAOYSA-N 2-amino-4-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C(N)=C1 LHMILTWCGKFWAI-UHFFFAOYSA-N 0.000 description 1
OXQJOAGKNHVOAI-UHFFFAOYSA-N 5-amino-6-methoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(N)C(OC)=CC=C21 OXQJOAGKNHVOAI-UHFFFAOYSA-N 0.000 description 1
GDAIYFAMMVNXNI-UHFFFAOYSA-N 5-ethoxy-2-methoxyaniline Chemical compound CCOC1=CC=C(OC)C(N)=C1 GDAIYFAMMVNXNI-UHFFFAOYSA-N 0.000 description 1
RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 description 1
ZLHGMJOGMLVDFS-UHFFFAOYSA-N 7-benzamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC(=O)C1=CC=CC=C1 ZLHGMJOGMLVDFS-UHFFFAOYSA-N 0.000 description 1
241000039077 Copula Species 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000005224 alkoxybenzenes Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000002500 ions Chemical class 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
239000011707 mineral Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
239000002964 rayon Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000003760 tallow Substances 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
230000037303 wrinkles Effects 0.000 description 1