DD142047A5 - Verfahren zur herstellung einer waessrigen aufschlaemmung einer azoverbindung - Google Patents
Verfahren zur herstellung einer waessrigen aufschlaemmung einer azoverbindung Download PDFInfo
- Publication number
- DD142047A5 DD142047A5 DD79211009A DD21100979A DD142047A5 DD 142047 A5 DD142047 A5 DD 142047A5 DD 79211009 A DD79211009 A DD 79211009A DD 21100979 A DD21100979 A DD 21100979A DD 142047 A5 DD142047 A5 DD 142047A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- coupling
- water
- feed stream
- sulfuric acid
- berlin
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000005859 coupling reaction Methods 0.000 claims description 67
- 238000010168 coupling process Methods 0.000 claims description 60
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 59
- 230000008878 coupling Effects 0.000 claims description 58
- -1 azo compound Chemical class 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 39
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 31
- 239000002002 slurry Substances 0.000 claims description 30
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 26
- 239000012528 membrane Substances 0.000 claims description 26
- 238000002156 mixing Methods 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 150000001989 diazonium salts Chemical class 0.000 claims description 21
- 239000004094 surface-active agent Substances 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 238000006193 diazotization reaction Methods 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000010790 dilution Methods 0.000 claims description 4
- 239000012895 dilution Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 3
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- 125000000217 alkyl group Chemical group 0.000 description 25
- 239000000126 substance Substances 0.000 description 24
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- 239000000376 reactant Substances 0.000 description 14
- 239000012954 diazonium Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- 125000003545 alkoxy group Chemical group 0.000 description 8
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- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000006386 neutralization reaction Methods 0.000 description 7
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- 239000002270 dispersing agent Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- 230000008901 benefit Effects 0.000 description 4
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- 238000011282 treatment Methods 0.000 description 4
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- TWAMXXLZDQNMCF-UHFFFAOYSA-N methyl 3-anilinopropanoate Chemical compound COC(=O)CCNC1=CC=CC=C1 TWAMXXLZDQNMCF-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
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- NDELSWXIAJLWOU-UHFFFAOYSA-N 2,5-dimethyl-4h-pyrazol-3-one Chemical compound CN1N=C(C)CC1=O NDELSWXIAJLWOU-UHFFFAOYSA-N 0.000 description 1
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- YJTBHWXNEMGNDC-UHFFFAOYSA-N 2-amino-1,3-thiazole-5-carbonitrile Chemical compound NC1=NC=C(C#N)S1 YJTBHWXNEMGNDC-UHFFFAOYSA-N 0.000 description 1
- RIYSFSQPHCAGLS-UHFFFAOYSA-N 2-amino-3,5-dinitrobenzonitrile Chemical compound NC1=C(C#N)C=C([N+]([O-])=O)C=C1[N+]([O-])=O RIYSFSQPHCAGLS-UHFFFAOYSA-N 0.000 description 1
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- XVYNBLCPQVDRCH-UHFFFAOYSA-N 2-amino-3-chloro-5-nitrobenzonitrile Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1C#N XVYNBLCPQVDRCH-UHFFFAOYSA-N 0.000 description 1
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- CFKZMYPOJOKAAD-UHFFFAOYSA-N 2-amino-5-nitrothiophene-3-carbonitrile Chemical compound NC=1SC([N+]([O-])=O)=CC=1C#N CFKZMYPOJOKAAD-UHFFFAOYSA-N 0.000 description 1
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- SVNCRRZKBNSMIV-UHFFFAOYSA-N 3-Aminoquinoline Chemical compound C1=CC=CC2=CC(N)=CN=C21 SVNCRRZKBNSMIV-UHFFFAOYSA-N 0.000 description 1
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- GJVMTMXQJDQJSS-UHFFFAOYSA-N 3-methyl-5-nitroimidazol-4-amine Chemical compound CN1C=NC([N+]([O-])=O)=C1N GJVMTMXQJDQJSS-UHFFFAOYSA-N 0.000 description 1
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- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
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- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000003854 isothiazoles Chemical class 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- XUBDTGBUGMAAHD-UHFFFAOYSA-N methyl 3-(5-acetamido-2-methoxy-n-(3-methoxy-3-oxopropyl)anilino)propanoate Chemical compound COC(=O)CCN(CCC(=O)OC)C1=CC(NC(C)=O)=CC=C1OC XUBDTGBUGMAAHD-UHFFFAOYSA-N 0.000 description 1
- VFPXZBJPIRXBGE-UHFFFAOYSA-N methyl 3-(n-(3-methoxy-3-oxopropyl)-3-methylanilino)propanoate Chemical compound COC(=O)CCN(CCC(=O)OC)C1=CC=CC(C)=C1 VFPXZBJPIRXBGE-UHFFFAOYSA-N 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- VIACAIAQHPLINF-UHFFFAOYSA-N n-benzyl-n-ethyl-3-methylaniline Chemical compound C=1C=CC(C)=CC=1N(CC)CC1=CC=CC=C1 VIACAIAQHPLINF-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical compound OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/006—Special methods of performing the coupling reaction characterised by process features
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
- C09B41/005—Special methods of performing the coupling reaction characterised by the coupling medium containing low molecular weight dispersing agents; containing surface active polythylene gylcols
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S534/00—Organic compounds -- part of the class 532-570 series
- Y10S534/07—Automatic and/or continuous temperature control in the preparation of azo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB581878 | 1978-02-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
DD142047A5 true DD142047A5 (de) | 1980-06-04 |
Family
ID=9803181
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD79211009A DD142047A5 (de) | 1978-02-14 | 1979-02-13 | Verfahren zur herstellung einer waessrigen aufschlaemmung einer azoverbindung |
Country Status (11)
Country | Link |
---|---|
US (1) | US4252718A (en, 2012) |
JP (1) | JPS54120636A (en, 2012) |
BE (1) | BE874077A (en, 2012) |
CH (1) | CH637982A5 (en, 2012) |
DD (1) | DD142047A5 (en, 2012) |
DE (1) | DE2903717A1 (en, 2012) |
ES (1) | ES477705A1 (en, 2012) |
FR (1) | FR2416924A1 (en, 2012) |
GB (1) | GB2021132B (en, 2012) |
IT (1) | IT1110291B (en, 2012) |
PL (1) | PL213342A1 (en, 2012) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2129434B (en) * | 1982-10-08 | 1986-04-16 | Ciba Geigy Ag | Production of azo compounds |
CH655125A5 (de) * | 1983-09-21 | 1986-03-27 | Ciba Geigy Ag | Verfahren zur herstellung von azofarbstoffpraeparaten. |
CH660494B (en, 2012) * | 1984-12-12 | 1987-04-30 | ||
TW233304B (en, 2012) * | 1992-04-02 | 1994-11-01 | Hoechst Mitsubishi Kasei | |
DE4447593C2 (de) | 1994-10-05 | 2000-12-07 | Clariant Gmbh | Toner für elektrophotographische Entwickler, enthaltend ein Azogelbpigment |
DE69910539T2 (de) * | 1998-01-29 | 2004-06-24 | Cabot Corp., Boston | Verfahren zur reinigung einer dispersion und herstellung von inkjet tinten |
US6346361B1 (en) * | 1999-10-06 | 2002-02-12 | Clariant Finance (Bvi) Limited | Method for synthesizing polymeric AZO dyes |
DE102004019560A1 (de) * | 2004-04-22 | 2005-11-10 | Clariant Gmbh | Hochreine Naphthol AS-Pigmente |
DE102004019561A1 (de) * | 2004-04-22 | 2005-11-10 | Clariant Gmbh | Verfahren zur Herstellung hochreiner Azofarbmittel |
GB0416256D0 (en) * | 2004-07-20 | 2004-08-25 | Avecia Ltd | Manufacturing process |
CN101054473B (zh) * | 2006-04-10 | 2010-10-20 | 浙江龙盛集团股份有限公司 | 一种耦合生产设备及生产工艺 |
CN104830089B (zh) * | 2015-04-29 | 2017-04-19 | 绍兴文理学院 | 一种染料连续偶合及减少能耗的方法 |
CN113634216B (zh) * | 2021-08-26 | 2022-05-31 | 大连理工大学 | 一种在管路式反应器中连续重氮化连续偶合生产水溶性偶氮染料的方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD77985A (en, 2012) * | ||||
CA572950A (en) * | 1959-03-24 | General Aniline And Film Corporation | Production of azoic pigments | |
US2478767A (en) * | 1945-10-04 | 1949-08-09 | Du Pont | Manufacture of azo compounds |
DE1231251B (de) * | 1963-11-28 | 1966-12-29 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Diazoverbindungen |
DE1934388B2 (de) * | 1969-07-07 | 1975-01-16 | Vyzkumny Ustav Organickych Syntez, Pardubice-Rybitvi (Tschechoslowakei) | Verfahren zur wiederholten Chargenherstellung von Azofarbstoffen |
US3793305A (en) * | 1970-09-14 | 1974-02-19 | Du Pont | One-step process of preparing azo dyes by simultaneous diazotization |
US4018751A (en) * | 1975-04-09 | 1977-04-19 | American Cyanamid Company | Continuous process for aminoazobenzene |
US4159264A (en) * | 1975-08-09 | 1979-06-26 | Ciba-Geigy Corporation | Automatic control of azo coupling processes in the manufacture of azo pigments |
-
1979
- 1979-01-31 DE DE19792903717 patent/DE2903717A1/de not_active Withdrawn
- 1979-01-31 GB GB7903441A patent/GB2021132B/en not_active Expired
- 1979-02-05 IT IT19904/79A patent/IT1110291B/it active
- 1979-02-09 BE BE0/193387A patent/BE874077A/xx not_active IP Right Cessation
- 1979-02-09 US US06/011,049 patent/US4252718A/en not_active Expired - Lifetime
- 1979-02-10 PL PL21334279A patent/PL213342A1/xx unknown
- 1979-02-13 FR FR7903607A patent/FR2416924A1/fr active Granted
- 1979-02-13 DD DD79211009A patent/DD142047A5/de unknown
- 1979-02-13 CH CH136479A patent/CH637982A5/de not_active IP Right Cessation
- 1979-02-14 ES ES477705A patent/ES477705A1/es not_active Expired
- 1979-02-14 JP JP1512779A patent/JPS54120636A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
CH637982A5 (de) | 1983-08-31 |
ES477705A1 (es) | 1979-10-16 |
US4252718A (en) | 1981-02-24 |
GB2021132B (en) | 1982-07-21 |
BE874077A (fr) | 1979-08-09 |
GB2021132A (en) | 1979-11-28 |
FR2416924B1 (en, 2012) | 1983-07-22 |
DE2903717A1 (de) | 1979-08-16 |
PL213342A1 (pl) | 1979-10-22 |
IT7919904A0 (it) | 1979-02-05 |
JPS54120636A (en) | 1979-09-19 |
FR2416924A1 (fr) | 1979-09-07 |
IT1110291B (it) | 1985-12-23 |
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