CA1058222A - Procede pour la fabrication au canada de pigments a base de benzidine et de derives de l'hydrazobenzene - Google Patents

Procede pour la fabrication au canada de pigments a base de benzidine et de derives de l'hydrazobenzene

Info

Publication number: CA1058222A
Authority: CA; Canada
Prior art keywords: parts; hydrazobenzene; solution; percent; filtered
Prior art date: 1975-10-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA236,973A

Other languages

English (en)

Other versions

CA236973S (en

Inventor

Harald Gleinig

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Colour Chem Ltd

Original Assignee

Colour Chem Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-10-03

Filing date

1975-10-03

Publication date

1979-07-10

1975-10-03 Application filed by Colour Chem Ltd filed Critical Colour Chem Ltd

1975-10-03 Priority to CA236,973A priority Critical patent/CA1058222A/fr

1979-07-10 Application granted granted Critical

1979-07-10 Publication of CA1058222A publication Critical patent/CA1058222A/fr

Status Expired legal-status Critical Current

Links

239000000049 pigment Substances 0.000 title claims abstract description 41
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 title claims abstract description 15
238000000034 method Methods 0.000 title claims abstract description 12
230000008569 process Effects 0.000 title claims abstract description 10
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical class NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 title claims description 22
238000004519 manufacturing process Methods 0.000 title abstract description 4
239000000243 solution Substances 0.000 claims description 44
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 claims description 34
230000008878 coupling Effects 0.000 claims description 23
238000010168 coupling process Methods 0.000 claims description 23
238000005859 coupling reaction Methods 0.000 claims description 23
239000007864 aqueous solution Substances 0.000 claims description 16
-1 methoxy, ethoxy Chemical group 0.000 claims description 13
GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 claims description 11
230000008707 rearrangement Effects 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
238000006193 diazotization reaction Methods 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
238000000746 purification Methods 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
238000003756 stirring Methods 0.000 abstract description 4
239000011541 reaction mixture Substances 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000007788 liquid Substances 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
238000001035 drying Methods 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
235000011121 sodium hydroxide Nutrition 0.000 description 10
IWKMQNKKYZERHI-UHFFFAOYSA-N 1,2-bis(2-chlorophenyl)hydrazine Chemical compound ClC1=CC=CC=C1NNC1=CC=CC=C1Cl IWKMQNKKYZERHI-UHFFFAOYSA-N 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
230000009467 reduction Effects 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 8
239000000843 powder Substances 0.000 description 8
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 8
235000019345 sodium thiosulphate Nutrition 0.000 description 8
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
239000003610 charcoal Substances 0.000 description 7
239000005457 ice water Substances 0.000 description 7
239000001632 sodium acetate Substances 0.000 description 7
235000017281 sodium acetate Nutrition 0.000 description 7
235000010288 sodium nitrite Nutrition 0.000 description 7
HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
238000007792 addition Methods 0.000 description 6
230000000875 corresponding effect Effects 0.000 description 6
230000007935 neutral effect Effects 0.000 description 6
239000007858 starting material Substances 0.000 description 6
NKUNBLUACJUHOA-UHFFFAOYSA-N (2-chlorophenyl)-(2-chlorophenyl)imino-oxidoazanium Chemical compound C=1C=CC=C(Cl)C=1[N+]([O-])=NC1=CC=CC=C1Cl NKUNBLUACJUHOA-UHFFFAOYSA-N 0.000 description 5
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 5
229960001760 dimethyl sulfoxide Drugs 0.000 description 5
HGVIAKXYAZRSEG-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1C HGVIAKXYAZRSEG-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
KVJYJSHGAOIUAH-UHFFFAOYSA-N (2-methoxyphenyl)-(2-methoxyphenyl)imino-oxidoazanium Chemical compound COC1=CC=CC=C1N=[N+]([O-])C1=CC=CC=C1OC KVJYJSHGAOIUAH-UHFFFAOYSA-N 0.000 description 4
OVZJNFMCLJEZQV-UHFFFAOYSA-N 1,2-bis(2-methoxyphenyl)hydrazine Chemical compound COC1=CC=CC=C1NNC1=CC=CC=C1OC OVZJNFMCLJEZQV-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
DNZMYLLBWKOXQJ-UHFFFAOYSA-N 1,2-bis(2,5-dichlorophenyl)hydrazine Chemical compound ClC1=CC=C(Cl)C(NNC=2C(=CC=C(Cl)C=2)Cl)=C1 DNZMYLLBWKOXQJ-UHFFFAOYSA-N 0.000 description 3
150000003931 anilides Chemical class 0.000 description 3
239000000975 dye Substances 0.000 description 3
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 3
OVXBYJMCICSXFP-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)hydrazine Chemical compound CC1=CC=CC=C1NNC1=CC=CC=C1C OVXBYJMCICSXFP-UHFFFAOYSA-N 0.000 description 2
AYJYYEJYADNRGM-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-2-(3-chlorophenyl)-1-methoxyhydrazine Chemical compound C=1C(Cl)=CC=C(OC)C=1N(OC)NC1=CC=CC(Cl)=C1 AYJYYEJYADNRGM-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000004133 Sodium thiosulphate Substances 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
238000013375 chromatographic separation Methods 0.000 description 2
QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 2
229940093476 ethylene glycol Drugs 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 2
MOUVJGIRLPZEES-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(NC(=O)CC(C)=O)=C(OC)C=C1Cl MOUVJGIRLPZEES-UHFFFAOYSA-N 0.000 description 2
ODFRAIZRJMUPCP-UHFFFAOYSA-N n-(4-chloro-2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1C ODFRAIZRJMUPCP-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
239000001052 yellow pigment Substances 0.000 description 2
DOEXABLGMSKMAO-UHFFFAOYSA-N (2,5-dichlorophenyl)-(2,5-dichlorophenyl)imino-oxidoazanium Chemical compound C=1C(Cl)=CC=C(Cl)C=1[N+]([O-])=NC1=CC(Cl)=CC=C1Cl DOEXABLGMSKMAO-UHFFFAOYSA-N 0.000 description 1
MBUVKGDWMUDLBP-UHFFFAOYSA-N (2-carboxyphenyl)-(2-carboxyphenyl)imino-oxidoazanium Chemical compound OC(=O)C1=CC=CC=C1N=[N+]([O-])C1=CC=CC=C1C(O)=O MBUVKGDWMUDLBP-UHFFFAOYSA-N 0.000 description 1
DRYVOVXFWWVZFW-UHFFFAOYSA-N (2-chloro-5-methoxyphenyl)-(2-chloro-5-methoxyphenyl)imino-oxidoazanium Chemical compound COC1=CC=C(Cl)C(N=[N+]([O-])C=2C(=CC=C(OC)C=2)Cl)=C1 DRYVOVXFWWVZFW-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
KLBVIRPOVIVOLL-UHFFFAOYSA-N 3-hydroxy-4-[[4-[4-[[2-hydroxy-3-[(2-methoxyphenyl)carbamoyl]naphthalen-1-yl]diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-N-(2-methoxyphenyl)naphthalene-2-carboxamide Chemical compound COc1ccccc1NC(=O)c1cc2ccccc2c(N=Nc2ccc(cc2OC)-c2ccc(N=Nc3c(O)c(cc4ccccc34)C(=O)Nc3ccccc3OC)c(OC)c2)c1O KLBVIRPOVIVOLL-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
XCRGXKMBFXAAQN-UHFFFAOYSA-N 4-(1-chlorocyclohexa-2,4-dien-1-yl)-5-methylpyrazol-3-one Chemical compound O=C1N=NC(C)=C1C1(Cl)C=CC=CC1 XCRGXKMBFXAAQN-UHFFFAOYSA-N 0.000 description 1
LPDSNGAFAJYVKH-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3-dichloroaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C(Cl)=C1Cl LPDSNGAFAJYVKH-UHFFFAOYSA-N 0.000 description 1
FWTBRYBHCBCJEQ-UHFFFAOYSA-N 4-[(4-phenyldiazenylnaphthalen-1-yl)diazenyl]phenol Chemical compound C1=CC(O)=CC=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC=C1 FWTBRYBHCBCJEQ-UHFFFAOYSA-N 0.000 description 1
YAVQZXBVUORYNQ-UHFFFAOYSA-N 5-methyl-2-(4-methylphenyl)-1h-pyrazol-3-one Chemical compound N1C(C)=CC(=O)N1C1=CC=C(C)C=C1 YAVQZXBVUORYNQ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
OORGGNYDIUQRDG-UHFFFAOYSA-N [3-[4-[(5-methyl-4-oxothieno[2,3-d][1,3]oxazin-2-yl)methyl]benzoyl]phenyl]-[3-[4-[(5-methyl-4-oxothieno[2,3-d][1,3]oxazin-2-yl)methyl]benzoyl]phenyl]imino-oxidoazanium Chemical compound O1C(=O)C=2C(C)=CSC=2N=C1CC(C=C1)=CC=C1C(=O)C(C=1)=CC=CC=1N=[N+]([O-])C(C=1)=CC=CC=1C(=O)C(C=C1)=CC=C1CC(OC1=O)=NC2=C1C(C)=CS2 OORGGNYDIUQRDG-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
DCCIFKZACWAKSD-UHFFFAOYSA-N ethyl 3-oxo-2-phenyl-1h-pyrazole-5-carboxylate Chemical compound N1C(C(=O)OCC)=CC(=O)N1C1=CC=CC=C1 DCCIFKZACWAKSD-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
IQWUCASGTZCNKK-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=C(NC(=O)CC(C)=O)C(OC)=C1 IQWUCASGTZCNKK-UHFFFAOYSA-N 0.000 description 1
PJFIAKRRJLGWMD-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=C(OC)C(NC(=O)CC(C)=O)=C1 PJFIAKRRJLGWMD-UHFFFAOYSA-N 0.000 description 1
KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 1
MJGLMEMIYDUEHA-UHFFFAOYSA-N n-(4-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1 MJGLMEMIYDUEHA-UHFFFAOYSA-N 0.000 description 1
AJDFNQRIAVDGQT-UHFFFAOYSA-N n-chloro-4-[4-(chloroamino)phenyl]aniline Chemical class C1=CC(NCl)=CC=C1C1=CC=C(NCl)C=C1 AJDFNQRIAVDGQT-UHFFFAOYSA-N 0.000 description 1
RUDCBGCNXOSCTI-UHFFFAOYSA-N n-methoxy-4-[4-(methoxyamino)phenyl]aniline Chemical compound C1=CC(NOC)=CC=C1C1=CC=C(NOC)C=C1 RUDCBGCNXOSCTI-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
JURVLDVTOYNZSG-UHFFFAOYSA-N oxido-(3-sulfophenyl)-(3-sulfophenyl)iminoazanium Chemical compound OS(=O)(=O)C1=CC=CC(N=[N+]([O-])C=2C=C(C=CC=2)S(O)(=O)=O)=C1 JURVLDVTOYNZSG-UHFFFAOYSA-N 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000004557 technical material Substances 0.000 description 1
238000004148 unit process Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA236,973A 1975-10-03 1975-10-03 Procede pour la fabrication au canada de pigments a base de benzidine et de derives de l'hydrazobenzene Expired CA1058222A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA236,973A CA1058222A (fr)	1975-10-03	1975-10-03	Procede pour la fabrication au canada de pigments a base de benzidine et de derives de l'hydrazobenzene

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA236,973A CA1058222A (fr)	1975-10-03	1975-10-03	Procede pour la fabrication au canada de pigments a base de benzidine et de derives de l'hydrazobenzene

Publications (1)

Publication Number	Publication Date
CA1058222A true CA1058222A (fr)	1979-07-10

Family

ID=4104195

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA236,973A Expired CA1058222A (fr)	1975-10-03	1975-10-03	Procede pour la fabrication au canada de pigments a base de benzidine et de derives de l'hydrazobenzene

Country Status (1)

Country	Link
CA (1)	CA1058222A (fr)

1975
- 1975-10-03 CA CA236,973A patent/CA1058222A/fr not_active Expired

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US2933489A (en)	1960-04-19	Heavy metal-containing dyestuffs
US2045090A (en)	1936-06-23	Cupriferous polyazo dyes and their production
JPH0549710B2 (fr)	1993-07-27
US4269769A (en)	1981-05-26	Diazo compounds obtained by coupling acetoacetanilides with tetrazotized diaminobenzanilides
US2155001A (en)	1939-04-18	Azo dyestuffs
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CA1058222A (fr)	1979-07-10	Procede pour la fabrication au canada de pigments a base de benzidine et de derives de l'hydrazobenzene
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US726667A (en)	1903-04-28	Blue basic dye and process of making same.
US658507A (en)	1900-09-25	Brown azo dye and process of making same.
US1766949A (en)	1930-06-24	x xxcho