BE431811A

BE431811A -

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Publication number: BE431811A
Authority: BE; Belgium
Prior art keywords: amino; acid; naphthol; dye; brown
Prior art date

Application number

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English (en)

French (fr)

Publication of BE431811A publication Critical patent/BE431811A/fr

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239000000975 dye Substances 0.000 claims description 77
239000000835 fiber Substances 0.000 claims description 37
230000001808 coupling Effects 0.000 claims description 34
238000010168 coupling process Methods 0.000 claims description 34
238000005859 coupling reaction Methods 0.000 claims description 34
239000000987 azo dye Substances 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
239000007787 solid Substances 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
230000002378 acidificating Effects 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
230000001264 neutralization Effects 0.000 claims description 4
230000001034 aminogenic Effects 0.000 claims description 3
239000004753 textile Substances 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 2
239000002253 acid Substances 0.000 description 102
210000002268 Wool Anatomy 0.000 description 24
238000006193 diazotization reaction Methods 0.000 description 21
239000000463 material Substances 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
229920000297 Rayon Polymers 0.000 description 14
239000003086 colorant Substances 0.000 description 12
230000000875 corresponding Effects 0.000 description 11
239000003513 alkali Substances 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000004043 dyeing Methods 0.000 description 8
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 7
150000001875 compounds Chemical class 0.000 description 7
239000002223 garnet Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
229910052802 copper Inorganic materials 0.000 description 6
239000010949 copper Substances 0.000 description 6
239000004744 fabric Substances 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
150000002828 nitro derivatives Chemical class 0.000 description 5
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 4
229920000742 Cotton Polymers 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
-1 benzene compound Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
HXXMONHYPKNZHE-UHFFFAOYSA-N 4-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 HXXMONHYPKNZHE-UHFFFAOYSA-N 0.000 description 3
QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000001049 brown dye Substances 0.000 description 3
239000000982 direct dye Substances 0.000 description 3
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000000203 mixture Substances 0.000 description 3
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 3
239000002964 rayon Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 2
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-Nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 2
FUXMQFBGQSNVBM-UHFFFAOYSA-N 4-methoxy-3-nitrobenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1[N+]([O-])=O FUXMQFBGQSNVBM-UHFFFAOYSA-N 0.000 description 2
ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 description 2
239000005751 Copper oxide Substances 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
WXWCDTXEKCVRRO-UHFFFAOYSA-N Para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
240000000358 Viola adunca Species 0.000 description 2
235000005811 Viola adunca Nutrition 0.000 description 2
235000013487 Viola odorata Nutrition 0.000 description 2
235000002254 Viola papilionacea Nutrition 0.000 description 2
229910052921 ammonium sulfate Inorganic materials 0.000 description 2
235000011130 ammonium sulphate Nutrition 0.000 description 2
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
QPLDLSVMHZLSFG-UHFFFAOYSA-N copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
229910000431 copper oxide Inorganic materials 0.000 description 2
230000027326 copulation Effects 0.000 description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000001187 sodium carbonate Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
230000003381 solubilizing Effects 0.000 description 2
230000001131 transforming Effects 0.000 description 2
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
CHLICZRVGGXEOD-UHFFFAOYSA-N 1-methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 1
POKNWSWQFXJOBG-UHFFFAOYSA-N 2-(3-aminophenyl)-5-methyl-1H-pyrazol-3-one Chemical compound N1C(C)=CC(=O)N1C1=CC=CC(N)=C1 POKNWSWQFXJOBG-UHFFFAOYSA-N 0.000 description 1
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
OZFUEQNYOBIXTB-VJOYVCHSSA-N 2-[(2E,5E)-5-[[4-[4-(2,2-diphenylethenyl)phenyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]indol-7-yl]methylidene]-2-(3-ethyl-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)-4-oxo-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC)C(=S)S\C1=C(\S\1)N(CC(O)=O)C(=O)C/1=C\C1=CC=C(N(C2C3CCC2)C=2C=CC(C=C(C=4C=CC=CC=4)C=4C=CC=CC=4)=CC=2)C3=C1 OZFUEQNYOBIXTB-VJOYVCHSSA-N 0.000 description 1
QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 1
NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
GICMHQJTKXNMGB-UHFFFAOYSA-N 4-(5-methoxy-1-benzofuran-2-yl)aniline Chemical compound C=1C2=CC(OC)=CC=C2OC=1C1=CC=C(N)C=C1 GICMHQJTKXNMGB-UHFFFAOYSA-N 0.000 description 1
JBORNNNGTJSTLC-UHFFFAOYSA-N 4-methoxy-1-methyl-2-nitrobenzene Chemical compound COC1=CC=C(C)C([N+]([O-])=O)=C1 JBORNNNGTJSTLC-UHFFFAOYSA-N 0.000 description 1
SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 1
FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-Anilinonaphthalene-1-sulfonic acid Chemical compound C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 description 1
HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N Ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
CHMBIJAOCISYEW-UHFFFAOYSA-N N-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
AWQLJVFEYFHNIC-UHFFFAOYSA-N NC1(CC=CC2=CC=CC=C12)N Chemical compound NC1(CC=CC2=CC=CC=C12)N AWQLJVFEYFHNIC-UHFFFAOYSA-N 0.000 description 1
HRDZLACUVIFYLS-UHFFFAOYSA-N NCC=1C(N=NC=1C1=CC=CC=C1)=O Chemical compound NCC=1C(N=NC=1C1=CC=CC=C1)=O HRDZLACUVIFYLS-UHFFFAOYSA-N 0.000 description 1
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
VEQOALNAAJBPNY-UHFFFAOYSA-N Phenazone Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000001166 ammonium sulphate 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
229950011260 betanaphthol Drugs 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
235000012709 brilliant black BN Nutrition 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
238000004040 coloring Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000000694 effects Effects 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
XKUUMWKWUZRRPD-UHFFFAOYSA-N heptan-2-amine;sulfuric acid Chemical compound [O-]S([O-])(=O)=O.CCCCCC(C)[NH3+].CCCCCC(C)[NH3+] XKUUMWKWUZRRPD-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
150000002736 metal compounds Chemical class 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
150000004780 naphthols Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000001184 potassium carbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000001047 purple dye Substances 0.000 description 1
239000001044 red dye Substances 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
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 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
230000001256 tonic Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1