BE545435A

BE545435A -

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Publication number: BE545435A
Authority: BE; Belgium
Prior art keywords: sep; group; hydroxybenzene; methyl; parts
Prior art date

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English (en)

French (fr)

Publication of BE545435A publication Critical patent/BE545435A/fr

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239000000975 dye Substances 0.000 claims description 47
239000011651 chromium Substances 0.000 claims description 18
-1 metal complex compounds Chemical class 0.000 claims description 14
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 13
229910001385 heavy metal Inorganic materials 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 8
229910052804 chromium Inorganic materials 0.000 claims description 8
230000001808 coupling Effects 0.000 claims description 8
238000010168 coupling process Methods 0.000 claims description 8
238000005859 coupling reaction Methods 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 6
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 6
239000000835 fiber Substances 0.000 claims description 6
125000004442 acylamino group Chemical group 0.000 claims description 5
IWDCLRJOBJJRNH-UHFFFAOYSA-N P-Cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 4
CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical compound N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 claims description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
229910052803 cobalt Inorganic materials 0.000 claims description 4
239000010941 cobalt Substances 0.000 claims description 4
229920001184 polypeptide Polymers 0.000 claims description 4
238000006193 diazotization reaction Methods 0.000 claims description 3
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
239000000987 azo dye Substances 0.000 claims 1
239000000463 material Substances 0.000 claims 1
150000002736 metal compounds Chemical class 0.000 claims 1
238000000034 method Methods 0.000 claims 1
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 104
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 13
210000002268 Wool Anatomy 0.000 description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000001914 filtration Methods 0.000 description 7
239000000203 mixture Substances 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
230000002378 acidificating Effects 0.000 description 6
238000001465 metallisation Methods 0.000 description 6
229960003742 phenol Drugs 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
238000004043 dyeing Methods 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
238000004532 chromating Methods 0.000 description 4
230000001264 neutralization Effects 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
230000000875 corresponding Effects 0.000 description 3
238000005755 formation reaction Methods 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000001187 sodium carbonate Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
GDLBFKVLRPITMI-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound ClC1=CC=C2NC(C)=NS(=O)(=O)C2=C1 GDLBFKVLRPITMI-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000007792 addition Methods 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
125000004429 atoms Chemical group 0.000 description 2
238000006149 azo coupling reaction Methods 0.000 description 2
229960004042 diazoxide Drugs 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
238000010992 reflux Methods 0.000 description 2
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-Xylidine Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 1
DUIOVGPUAJSYCD-UHFFFAOYSA-N 2,4-dimethyl-5-nitroaniline Chemical compound CC1=CC(C)=C([N+]([O-])=O)C=C1N DUIOVGPUAJSYCD-UHFFFAOYSA-N 0.000 description 1
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
AKNUHUCEWALCOI-UHFFFAOYSA-N 2-[ethyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
JEASLLCHQHBBGM-UHFFFAOYSA-N 2-amino-4,5-dimethylphenol Chemical compound CC1=CC(N)=C(O)C=C1C JEASLLCHQHBBGM-UHFFFAOYSA-N 0.000 description 1
WASQBNCGNUTVNI-UHFFFAOYSA-N 2-amino-4,6-dichlorophenol Chemical compound NC1=CC(Cl)=CC(Cl)=C1O WASQBNCGNUTVNI-UHFFFAOYSA-N 0.000 description 1
ZARYBZGMUVAJMK-UHFFFAOYSA-N 2-amino-4-chloro-5-nitrophenol Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1O ZARYBZGMUVAJMK-UHFFFAOYSA-N 0.000 description 1
MHAFRUMLQZZSIN-UHFFFAOYSA-N 2-amino-4-chloro-6-nitrophenol Chemical compound NC1=CC(Cl)=CC([N+]([O-])=O)=C1O MHAFRUMLQZZSIN-UHFFFAOYSA-N 0.000 description 1
SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 1
WZSBYBXNPKFJTA-UHFFFAOYSA-N 2-amino-4-methyl-5-nitrophenol Chemical compound CC1=CC(N)=C(O)C=C1[N+]([O-])=O WZSBYBXNPKFJTA-UHFFFAOYSA-N 0.000 description 1
AJWIWEGQLDDWQC-UHFFFAOYSA-N 2-amino-4-methyl-6-nitrophenol Chemical compound CC1=CC(N)=C(O)C([N+]([O-])=O)=C1 AJWIWEGQLDDWQC-UHFFFAOYSA-N 0.000 description 1
ZDMBLPBTZZZSIW-UHFFFAOYSA-N 2-amino-6-methyl-4-nitrophenol Chemical compound CC1=CC([N+]([O-])=O)=CC(N)=C1O ZDMBLPBTZZZSIW-UHFFFAOYSA-N 0.000 description 1
NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-UHFFFAOYSA-N 0.000 description 1
YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-Xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
RHPXYZMDLOJTFF-UHFFFAOYSA-N 3-Amino-4-hydroxy-5-nitrobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC([N+]([O-])=O)=C1O RHPXYZMDLOJTFF-UHFFFAOYSA-N 0.000 description 1
DQIVFTJHYKDOMZ-UHFFFAOYSA-N 96-67-3 Chemical compound NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O DQIVFTJHYKDOMZ-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
KYFWKVPNFRBWMW-UHFFFAOYSA-N CC(=O)NC1=CC(O)=C(C)C=C1C Chemical compound CC(=O)NC1=CC(O)=C(C)C=C1C KYFWKVPNFRBWMW-UHFFFAOYSA-N 0.000 description 1
FMUDEDGROOYXOL-UHFFFAOYSA-N CS(=O)(=O)C1=CC(N)=C(O)C(Cl)=C1 Chemical compound CS(=O)(=O)C1=CC(N)=C(O)C(Cl)=C1 FMUDEDGROOYXOL-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
WRLJFWNMYGBFOC-UHFFFAOYSA-Q Chrome complex Chemical compound [H+].[H+].[Cr].CCCCC(CC)COCCCN.CCCCC(CC)COCCCN.O=C1[C-](N=NC=2C(=C(C=C(C=2)[N+]([O-])=O)S(O)(=O)=O)O)C(C)=NN1C1=CC=CC=C1.O=C1[C-](N=NC=2C(=C(C=C(C=2)[N+]([O-])=O)S(O)(=O)=O)O)C(C)=NN1C1=CC=CC=C1.C=12C=CC(N(CC)CC)=CC2=[O+]C2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O WRLJFWNMYGBFOC-UHFFFAOYSA-Q 0.000 description 1
QAHREYKOYSIQPH-UHFFFAOYSA-L Cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium Ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
210000004080 Milk Anatomy 0.000 description 1
DWXIXAXNKTUUPM-UHFFFAOYSA-N N-(2-hydroxy-4,5-dimethylphenyl)acetamide Chemical compound CC(=O)NC1=CC(C)=C(C)C=C1O DWXIXAXNKTUUPM-UHFFFAOYSA-N 0.000 description 1
KJFMBFZCATUALV-UHFFFAOYSA-N Phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
XMXNVYPJWBTAHN-UHFFFAOYSA-N Potassium chromate Chemical compound [K+].[K+].[O-][Cr]([O-])(=O)=O XMXNVYPJWBTAHN-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 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
150000003863 ammonium salts Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
150000001844 chromium Chemical class 0.000 description 1
150000001868 cobalt Chemical class 0.000 description 1
229940011182 cobalt acetate Drugs 0.000 description 1
PJQDFOMVKDFESH-UHFFFAOYSA-N cobalt(2+);N-(9H-fluoren-2-yl)-N-oxidoacetamide Chemical class [Co+2].C1=CC=C2C3=CC=C(N([O-])C(=O)C)C=C3CC2=C1.C1=CC=C2C3=CC=C(N([O-])C(=O)C)C=C3CC2=C1 PJQDFOMVKDFESH-UHFFFAOYSA-N 0.000 description 1
NERQXUOKJAXUHN-UHFFFAOYSA-L cobalt(3+);2-[3-[3-[(2-oxidophenyl)methylideneamino]propylazanidyl]propyliminomethyl]phenolate Chemical compound [Co+3].[O-]C1=CC=CC=C1C=NCCC[N-]CCCN=CC1=CC=CC=C1[O-] NERQXUOKJAXUHN-UHFFFAOYSA-L 0.000 description 1
230000027326 copulation Effects 0.000 description 1
150000004665 fatty acids Chemical group 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001131 transforming Effects 0.000 description 1