JP2518843B2 - アゾ染料の製法 - Google Patents
アゾ染料の製法Info
- Publication number
- JP2518843B2 JP2518843B2 JP62106489A JP10648987A JP2518843B2 JP 2518843 B2 JP2518843 B2 JP 2518843B2 JP 62106489 A JP62106489 A JP 62106489A JP 10648987 A JP10648987 A JP 10648987A JP 2518843 B2 JP2518843 B2 JP 2518843B2
- Authority
- JP
- Japan
- Prior art keywords
- coupling
- component
- azo dye
- coupling component
- azo
- Prior art date
- 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 - Lifetime
Links
- 239000000987 azo dye Substances 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title description 5
- 230000008878 coupling Effects 0.000 claims description 39
- 238000010168 coupling process Methods 0.000 claims description 39
- 238000005859 coupling reaction Methods 0.000 claims description 39
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 238000006149 azo coupling reaction Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 239000012928 buffer substance Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 239000012954 diazonium Substances 0.000 description 11
- 150000001989 diazonium salts Chemical class 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 2
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 2
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 2
- -1 allylacetidoacetates Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000008395 clarifying agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000003801 milling Methods 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
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3615099.1 | 1986-05-03 | ||
| DE3615099 | 1986-05-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62263260A JPS62263260A (ja) | 1987-11-16 |
| JP2518843B2 true JP2518843B2 (ja) | 1996-07-31 |
Family
ID=6300157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62106489A Expired - Lifetime JP2518843B2 (ja) | 1986-05-03 | 1987-05-01 | アゾ染料の製法 |
Country Status (9)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN169308B (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) * | 1986-05-03 | 1991-09-28 | Hoechst Ag | |
| GB2235694B (en) * | 1989-08-10 | 1992-06-24 | Ciba Geigy Ag | Process for the preparation of bisazo pigment mixtures |
| US5191070A (en) * | 1989-08-10 | 1993-03-02 | Ciba-Geigy Corporation | Continuous process for the preparation of bisazo pigment mixtures |
| WO1997031067A1 (fr) * | 1996-02-26 | 1997-08-28 | Toyo Ink Manufacturing Co., Ltd. | Procede de preparation de pigments disazoiques et pigments disazoiques produits par ce procede |
| ES2208549T3 (es) * | 2000-02-09 | 2004-06-16 | Clariant Finance (Bvi) Limited | Procedimiento para la produccion de agentes colorantes azoicos en microrreactores. |
| US7135266B2 (en) | 2000-02-09 | 2006-11-14 | Clariant Finance (Bvi) Limited | Preparation of azo colorants in microreactors and their use in electrophotographic toners and developers, powder coatings, ink jet inks and electronic medias |
| IL154536A0 (en) * | 2000-08-29 | 2003-09-17 | Nobex Corp | Immunoregulatory compounds and derivatives and methods of treating diseases therewith |
| DE10049200A1 (de) | 2000-10-05 | 2002-04-11 | Clariant Gmbh | Verfahren zur Herstellung von Azofarbmitteln |
| US8048924B2 (en) * | 2001-08-29 | 2011-11-01 | Biocon Limited | Methods and compositions employing 4-aminophenylacetic acid compounds |
| ES2565848T3 (es) | 2004-07-07 | 2016-04-07 | Biocon Limited | Síntesis de compuestos inmunorreguladores unidos por grupos azoicos |
| GB0416256D0 (en) * | 2004-07-20 | 2004-08-25 | Avecia Ltd | Manufacturing process |
| US20080108736A1 (en) * | 2004-12-03 | 2008-05-08 | Canon Kabushiki Kaisha | Preparation Process Of Azo Pigment Dispersion |
| 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 |
| CN116283650B (zh) * | 2022-12-29 | 2025-08-01 | 利安隆（中卫）新材料有限公司 | 一种苯并三氮唑类光稳定剂中间体的连续制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2174954A (en) * | 1937-03-22 | 1939-10-03 | Harmon Color Works Inc | Azo pigment and method of preparing |
| GB599608A (en) * | 1942-12-22 | 1948-03-17 | Gen Printing Ink Corp | Improvements in or relating to the production of monazo and disazo pigments |
| DE1085278B (de) * | 1958-03-08 | 1960-07-14 | Hoechst Ag | Verfahren zur kontinuierlichen Herstellung von Azopigmenten |
| GB1143727A (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) * | 1966-09-09 | 1900-01-01 | ||
| DE2844634A1 (de) * | 1978-10-13 | 1980-04-24 | Hoechst Ag | Verfahren zur kontinuierlichen herstellung von azopigmenten |
| US4395264A (en) * | 1981-11-06 | 1983-07-26 | Basf Wyandotte Corporation | Azo coupling process |
| GB2129434B (en) * | 1982-10-08 | 1986-04-16 | Ciba Geigy Ag | Production of azo compounds |
| IN169308B (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) * | 1986-05-03 | 1991-09-28 | Hoechst Ag |
-
1987
- 1987-03-26 IN IN219/MAS/87A patent/IN169307B/en unknown
- 1987-04-18 EP EP87105765A patent/EP0244686B1/de not_active Expired - Lifetime
- 1987-04-18 DE DE8787105765T patent/DE3783646D1/de not_active Expired - Lifetime
- 1987-04-18 ES ES87105765T patent/ES2044859T3/es not_active Expired - Lifetime
- 1987-05-01 JP JP62106489A patent/JP2518843B2/ja not_active Expired - Lifetime
- 1987-05-01 AU AU72406/87A patent/AU595601B2/en not_active Ceased
- 1987-05-01 DK DK223587A patent/DK167224B1/da not_active IP Right Cessation
- 1987-05-01 KR KR1019870004279A patent/KR950009539B1/ko not_active Expired - Fee Related
-
1989
- 1989-03-29 US US07/329,953 patent/US4920206A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4920206A (en) | 1990-04-24 |
| KR880009100A (ko) | 1988-09-14 |
| KR950009539B1 (ko) | 1995-08-24 |
| AU595601B2 (en) | 1990-04-05 |
| EP0244686A2 (de) | 1987-11-11 |
| DK223587D0 (da) | 1987-05-01 |
| DK167224B1 (da) | 1993-09-20 |
| JPS62263260A (ja) | 1987-11-16 |
| EP0244686A3 (en) | 1990-11-14 |
| ES2044859T3 (es) | 1994-01-16 |
| IN169307B (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | 1991-09-28 |
| AU7240687A (en) | 1987-11-05 |
| DK223587A (da) | 1987-11-04 |
| DE3783646D1 (de) | 1993-03-04 |
| EP0244686B1 (de) | 1993-01-20 |
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