BE532338A

BE532338A -

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Publication number: BE532338A
Authority: BE; Belgium
Prior art keywords: denotes; residue; amino; formula; dyes
Prior art date

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English (en)

French (fr)

Publication of BE532338A publication Critical patent/BE532338A/fr

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239000000975 dye Substances 0.000 claims description 46
-1 aminomonoazo Chemical group 0.000 claims description 15
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 14
230000000875 corresponding Effects 0.000 claims description 9
125000005647 linker group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
239000000463 material Substances 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 3
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 2
125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 2
238000000034 method Methods 0.000 claims description 2
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims 1
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
XRMLOZSMCSUBTL-UHFFFAOYSA-N phenylazanide Chemical group [NH-]C1=CC=CC=C1 XRMLOZSMCSUBTL-UHFFFAOYSA-N 0.000 claims 1
239000002253 acid Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
239000007859 condensation product Substances 0.000 description 8
150000001879 copper Chemical class 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
230000001808 coupling Effects 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
238000005406 washing Methods 0.000 description 6
229920000742 Cotton Polymers 0.000 description 5
150000001412 amines Chemical group 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
229920002678 cellulose Polymers 0.000 description 5
239000001913 cellulose Substances 0.000 description 5
IQGMRVWUTCYCST-UHFFFAOYSA-N 3-Aminosalicylic acid Chemical class NC1=CC=CC(C(O)=O)=C1O IQGMRVWUTCYCST-UHFFFAOYSA-N 0.000 description 4
MGNCLNQXLYJVJD-UHFFFAOYSA-N Cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000243 solution Substances 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 3
KBOPZPXVLCULAV-UHFFFAOYSA-N Mesalazine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 3
YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
XFXPMWWXUTWYJX-UHFFFAOYSA-N cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
239000001187 sodium carbonate Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
YUDGWDNZKSVTHL-UHFFFAOYSA-N 2-(1-aminonaphthalen-2-yl)oxyacetic acid Chemical compound C1=CC=C2C(N)=C(OCC(O)=O)C=CC2=C1 YUDGWDNZKSVTHL-UHFFFAOYSA-N 0.000 description 2
ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
229920003043 Cellulose fiber Polymers 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical compound N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 2
230000027326 copulation Effects 0.000 description 2
239000000835 fiber Substances 0.000 description 2
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 2
239000000203 mixture Substances 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000004627 regenerated cellulose Substances 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
HKWPUUYEGGDLJF-UHFFFAOYSA-N 4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HKWPUUYEGGDLJF-UHFFFAOYSA-N 0.000 description 1
PYZAJVNHGMYHFW-UHFFFAOYSA-N 5-amino-2-hydroxy-3-methylbenzoic acid Chemical compound CC1=CC(N)=CC(C(O)=O)=C1O PYZAJVNHGMYHFW-UHFFFAOYSA-N 0.000 description 1
SGAMDQAWRICYND-UHFFFAOYSA-N 5-amino-3-chloro-2-hydroxybenzoic acid Chemical compound NC1=CC(Cl)=C(O)C(C(O)=O)=C1 SGAMDQAWRICYND-UHFFFAOYSA-N 0.000 description 1
KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
HUYJTJXLNBOVFO-UHFFFAOYSA-N 7-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(O)=CC=C21 HUYJTJXLNBOVFO-UHFFFAOYSA-N 0.000 description 1
SYMAOPXKWWZQIR-UHFFFAOYSA-N 8-hydroxynaphthalene-2-sulfonic acid Chemical class C1=C(S(O)(=O)=O)C=C2C(O)=CC=CC2=C1 SYMAOPXKWWZQIR-UHFFFAOYSA-N 0.000 description 1
241000974482 Aricia saepiolus Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
239000005749 Copper compound Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
LHXKXHDREJPGFY-UHFFFAOYSA-N NC1=CC=C(C(=O)C=2C=C(C(=C(C(=O)O)C2)O)N)C=C1 Chemical compound NC1=CC=C(C(=O)C=2C=C(C(=C(C(=O)O)C2)O)N)C=C1 LHXKXHDREJPGFY-UHFFFAOYSA-N 0.000 description 1
HOAYMSXUKFNSIC-UHFFFAOYSA-N NC1=CC=CC=C1.NC1=CC=CC(C(O)=O)=C1 Chemical compound NC1=CC=CC=C1.NC1=CC=CC(C(O)=O)=C1 HOAYMSXUKFNSIC-UHFFFAOYSA-N 0.000 description 1
XARHSLOUYFGEDH-UHFFFAOYSA-N NCOC1=C(C=CC2=CC(=CC=C12)S(=O)(=O)O)C(=O)O Chemical compound NCOC1=C(C=CC2=CC(=CC=C12)S(=O)(=O)O)C(=O)O XARHSLOUYFGEDH-UHFFFAOYSA-N 0.000 description 1
UEVHGNXDRLEBEW-UHFFFAOYSA-N NCOC1=C(C=CC2=CC=CC=C12)C(=O)O Chemical compound NCOC1=C(C=CC2=CC=CC=C12)C(=O)O UEVHGNXDRLEBEW-UHFFFAOYSA-N 0.000 description 1
HELHAJAZNSDZJO-UHFFFAOYSA-L Sodium tartrate Chemical compound [Na+].[Na+].[O-]C(=O)C(O)C(O)C([O-])=O HELHAJAZNSDZJO-UHFFFAOYSA-L 0.000 description 1
229960002167 Sodium tartrate Drugs 0.000 description 1
210000002268 Wool Anatomy 0.000 description 1
239000000980 acid dye Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
150000001880 copper compounds Chemical class 0.000 description 1
RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
239000000982 direct dye Substances 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
230000001264 neutralization Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000007747 plating Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001433 sodium tartrate Substances 0.000 description 1
235000011004 sodium tartrates Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 1