BE529478A

BE529478A -

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Publication number: BE529478A
Authority: BE; Belgium
Prior art keywords: dyes; parts; dye; acid; compound
Prior art date

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English (en)

French (fr)

Publication of BE529478A publication Critical patent/BE529478A/fr

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239000000975 dye Substances 0.000 claims description 113
239000002253 acid Substances 0.000 claims description 33
-1 polyazo Polymers 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 21
RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 15
229910052802 copper Inorganic materials 0.000 claims description 15
239000010949 copper Substances 0.000 claims description 15
230000000875 corresponding Effects 0.000 claims description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
229920002678 cellulose Polymers 0.000 claims description 10
239000001913 cellulose Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 9
229910001385 heavy metal Inorganic materials 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 7
150000004696 coordination complex Chemical class 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
150000008049 diazo compounds Chemical class 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 5
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 5
150000002790 naphthalenes Chemical class 0.000 claims description 5
230000001264 neutralization Effects 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 3
125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 2
SGBQUMZTGSQNAO-UHFFFAOYSA-N 2-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(O)=CC=C21 SGBQUMZTGSQNAO-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
230000004048 modification Effects 0.000 claims description 2
238000006011 modification reaction Methods 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 32
230000001808 coupling Effects 0.000 description 18
238000010168 coupling process Methods 0.000 description 18
238000005859 coupling reaction Methods 0.000 description 18
239000000243 solution Substances 0.000 description 17
239000001187 sodium carbonate Substances 0.000 description 16
229910000029 sodium carbonate Inorganic materials 0.000 description 16
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 15
229920000742 Cotton Polymers 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
230000037303 wrinkles Effects 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000000463 material Substances 0.000 description 9
XQAFHGXXHIZSGZ-UHFFFAOYSA-N 8-hydroxynaphthalene-1,6-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 XQAFHGXXHIZSGZ-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000000835 fiber Substances 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 6
JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 5
ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 5
150000001879 copper Chemical class 0.000 description 5
150000001880 copper compounds Chemical class 0.000 description 5
238000006193 diazotization reaction Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000005406 washing Methods 0.000 description 5
RWZYAGGXGHYGMB-UHFFFAOYSA-N Anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
239000005749 Copper compound Substances 0.000 description 4
210000002268 Wool Anatomy 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000002585 base Substances 0.000 description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
229910052803 cobalt Inorganic materials 0.000 description 4
239000010941 cobalt Substances 0.000 description 4
PBTUTICKCLVZAB-ZJVSAGCXSA-H copper;tetrasodium;7-[[4-(2-hydroxyethylamino)-6-[[(6E)-6-[(2-oxido-5-sulfonatophenyl)hydrazinylidene]-5-oxo-7-sulfonatonaphthalen-2-yl]amino]-1,3,5-triazin-2-yl]amino]-3-[(4-methoxy-2-sulfonatophenyl)diazenyl]-4-oxidonaphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].[O-]S(=O)(=O)C1=CC(OC)=CC=C1N=NC(C(=CC1=C2)S([O-])(=O)=O)=C([O-])C1=CC=C2NC1=NC(NCCO)=NC(NC=2C=C3C=C(C(=N/NC=4C(=CC=C(C=4)S([O-])(=O)=O)[O-])/C(=O)C3=CC=2)S([O-])(=O)=O)=N1 PBTUTICKCLVZAB-ZJVSAGCXSA-H 0.000 description 4
238000004043 dyeing Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
AVQFHKYAVVQYQO-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonamide Chemical compound NC1=CC(S(N)(=O)=O)=CC=C1O AVQFHKYAVVQYQO-UHFFFAOYSA-N 0.000 description 3
ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical class NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating Effects 0.000 description 3
239000000987 azo dye Substances 0.000 description 3
150000001555 benzenes Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000004305 biphenyl Substances 0.000 description 3
125000006267 biphenyl group Chemical group 0.000 description 3
239000003086 colorant Substances 0.000 description 3
229910000365 copper sulfate Inorganic materials 0.000 description 3
230000002349 favourable Effects 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
CLBQHDAKOPHNQI-UHFFFAOYSA-N 3-amino-2-hydroxynaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(O)(=O)=O)=C(O)C(N)=CC2=C1 CLBQHDAKOPHNQI-UHFFFAOYSA-N 0.000 description 2
TZBROGJRQUABOK-UHFFFAOYSA-N 4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 TZBROGJRQUABOK-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
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 2
HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
MGNCLNQXLYJVJD-UHFFFAOYSA-N Cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
WASQWSOJHCZDFK-UHFFFAOYSA-N Diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 2
230000027326 copulation Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
150000002736 metal compounds Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
238000007747 plating Methods 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000002194 synthesizing Effects 0.000 description 2
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-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
JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-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
SFLMBHYNCSYPOO-UHFFFAOYSA-N 2-amino-4-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=C(O)C(N)=C1 SFLMBHYNCSYPOO-UHFFFAOYSA-N 0.000 description 1
QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
BLGJHQMNSBYLEZ-UHFFFAOYSA-N 2-hydroxyethanesulfonamide Chemical compound NS(=O)(=O)CCO BLGJHQMNSBYLEZ-UHFFFAOYSA-N 0.000 description 1
ZWTZHHHSRDUVRT-UHFFFAOYSA-N 2-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=CC=C1O ZWTZHHHSRDUVRT-UHFFFAOYSA-N 0.000 description 1
QGTXBWMKRGHPDD-UHFFFAOYSA-N 3-amino-5-chloro-4-hydroxybenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(Cl)=C1O QGTXBWMKRGHPDD-UHFFFAOYSA-N 0.000 description 1
OXPHXVVDAJRNTR-UHFFFAOYSA-N 3-hydroxy-7-(3-oxobutanoylamino)naphthalene-1-sulfonic acid Chemical compound C1=C(O)C=C(S(O)(=O)=O)C2=CC(NC(=O)CC(=O)C)=CC=C21 OXPHXVVDAJRNTR-UHFFFAOYSA-N 0.000 description 1
RZMZJYAMZGWBLB-UHFFFAOYSA-N 3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=CC(O)=CC(S(O)(=O)=O)=C21 RZMZJYAMZGWBLB-UHFFFAOYSA-N 0.000 description 1
USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 description 1
LCYKXQBQVQHIIQ-UHFFFAOYSA-N 4-hydroxy-5-(3-oxobutanoylamino)naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(NC(=O)CC(=O)C)=CC(S(O)(=O)=O)=CC2=C1 LCYKXQBQVQHIIQ-UHFFFAOYSA-N 0.000 description 1
XZDYYPDENBXOCV-UHFFFAOYSA-N 4-hydroxy-6-(3-oxobutanoylamino)naphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(NC(=O)CC(=O)C)=CC=C21 XZDYYPDENBXOCV-UHFFFAOYSA-N 0.000 description 1
URWOXJLZMALVGZ-UHFFFAOYSA-N 4-hydroxy-7-(3-oxobutanoylamino)naphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC(=O)CC(=O)C)=CC=C21 URWOXJLZMALVGZ-UHFFFAOYSA-N 0.000 description 1
XIQKALDENTUXBY-UHFFFAOYSA-N 4-hydroxynaphthalene-1,5-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 XIQKALDENTUXBY-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
VLDABBRVDVXQPV-UHFFFAOYSA-N 5-amino-6-hydroxynaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=C(O)C=CC2=C1 VLDABBRVDVXQPV-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
YKVBYISUDGOVDM-UHFFFAOYSA-N 6-acetamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(NC(=O)C)=CC=C21 YKVBYISUDGOVDM-UHFFFAOYSA-N 0.000 description 1
QDQYVGHTDXWLCN-UHFFFAOYSA-N 6-nitronaphthalen-2-ol Chemical compound C1=C([N+]([O-])=O)C=CC2=CC(O)=CC=C21 QDQYVGHTDXWLCN-UHFFFAOYSA-N 0.000 description 1
KKAMNIDZQVXDJV-UHFFFAOYSA-N 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC(=O)C)=CC=C21 KKAMNIDZQVXDJV-UHFFFAOYSA-N 0.000 description 1
NWYPJANFHLUNFH-UHFFFAOYSA-N 7-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=C(O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 NWYPJANFHLUNFH-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
DOBIZWYVJFIYOV-UHFFFAOYSA-N 7-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(O)=CC=C21 DOBIZWYVJFIYOV-UHFFFAOYSA-N 0.000 description 1
GGZZISOUXJHYOY-UHFFFAOYSA-N 8-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1O GGZZISOUXJHYOY-UHFFFAOYSA-N 0.000 description 1
KVHHMYZBFBSVDI-UHFFFAOYSA-N 8-aminonaphthalen-2-ol Chemical class C1=C(O)C=C2C(N)=CC=CC2=C1 KVHHMYZBFBSVDI-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
229920003043 Cellulose fiber Polymers 0.000 description 1
HLVXFWDLRHCZEI-UHFFFAOYSA-N Chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 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
JJSXFCXOBHVXDG-UHFFFAOYSA-N NC=1CC(C=CC1)(S(=O)(=O)O)O Chemical compound NC=1CC(C=CC1)(S(=O)(=O)O)O JJSXFCXOBHVXDG-UHFFFAOYSA-N 0.000 description 1
229940099990 Ogen Drugs 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
JYSYDMOTQQTCKC-UHFFFAOYSA-N S(=O)(=O)(O)C=1C=C(C=CC1)C1=C(C2=CC(=CC(=C2C=C1)O)S(=O)(=O)O)N Chemical compound S(=O)(=O)(O)C=1C=C(C=CC1)C1=C(C2=CC(=CC(=C2C=C1)O)S(=O)(=O)O)N JYSYDMOTQQTCKC-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
FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
YDQUCWMQMWNPLR-UHFFFAOYSA-N [ethyl(sulfamoyl)amino]ethane Chemical compound CCN(CC)S(N)(=O)=O YDQUCWMQMWNPLR-UHFFFAOYSA-N 0.000 description 1
QMHAHUAQAJVBIW-UHFFFAOYSA-N [methyl(sulfamoyl)amino]methane Chemical compound CN(C)S(N)(=O)=O QMHAHUAQAJVBIW-UHFFFAOYSA-N 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000004429 atoms Chemical group 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229940011182 cobalt acetate Drugs 0.000 description 1
150000001869 cobalt compounds Chemical class 0.000 description 1
238000004040 coloring Methods 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000001465 metallisation Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000011707 mineral 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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000001433 sodium tartrate Substances 0.000 description 1
235000011004 sodium tartrates Nutrition 0.000 description 1
229960001663 sulfanilamide Drugs 0.000 description 1
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150000003456 sulfonamides Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 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
125000005270 trialkylamine group Chemical group 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1