AU594760B2 - Process for making azo pigments - Google Patents
Process for making azo pigments Download PDFInfo
- Publication number
- AU594760B2 AU594760B2 AU72407/87A AU7240787A AU594760B2 AU 594760 B2 AU594760 B2 AU 594760B2 AU 72407/87 A AU72407/87 A AU 72407/87A AU 7240787 A AU7240787 A AU 7240787A AU 594760 B2 AU594760 B2 AU 594760B2
- Authority
- AU
- Australia
- Prior art keywords
- acid
- reaction
- coupling component
- coupling
- reaction step
- 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.)
- Ceased
Links
- 239000000049 pigment Substances 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 13
- 230000008878 coupling Effects 0.000 claims description 41
- 238000010168 coupling process Methods 0.000 claims description 41
- 238000005859 coupling reaction Methods 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 239000000243 solution Substances 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 16
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 238000006149 azo coupling reaction Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000006172 buffering agent Substances 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 3
- 229940031826 phenolate Drugs 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 239000003643 water by type Substances 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 150000001989 diazonium salts Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 3
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000008395 clarifying agent Substances 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000005457 ice water Substances 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
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent 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)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Paints Or Removers (AREA)
- Photoreceptors In Electrophotography (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3615100 | 1986-05-03 | ||
| DE3615100 | 1986-05-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7240787A AU7240787A (en) | 1987-11-05 |
| AU594760B2 true AU594760B2 (en) | 1990-03-15 |
Family
ID=6300159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU72407/87A Ceased AU594760B2 (en) | 1986-05-03 | 1987-05-01 | Process for making azo pigments |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0244687B1 (enrdf_load_stackoverflow) |
| JP (1) | JPH0784566B2 (enrdf_load_stackoverflow) |
| KR (1) | KR960008248B1 (enrdf_load_stackoverflow) |
| AU (1) | AU594760B2 (enrdf_load_stackoverflow) |
| DE (1) | DE3782966D1 (enrdf_load_stackoverflow) |
| DK (1) | DK168394B1 (enrdf_load_stackoverflow) |
| ES (1) | ES2037023T3 (enrdf_load_stackoverflow) |
| IN (1) | IN169308B (enrdf_load_stackoverflow) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN169307B (enrdf_load_stackoverflow) * | 1986-05-03 | 1991-09-28 | Hoechst Ag | |
| DE3932829C1 (enrdf_load_stackoverflow) * | 1989-09-30 | 1991-05-02 | Ciba-Geigy Ag, Basel, Ch | |
| DE4447593C2 (de) | 1994-10-05 | 2000-12-07 | Clariant Gmbh | Toner für elektrophotographische Entwickler, enthaltend ein Azogelbpigment |
| US6099635A (en) * | 1999-04-09 | 2000-08-08 | Lonza Ag | Acetoacetylated suspensions in pigment applications |
| JP2006028341A (ja) * | 2004-07-16 | 2006-02-02 | Toyo Ink Mfg Co Ltd | ジスアゾ顔料の製造方法及びジスアゾ顔料 |
| GB0416256D0 (en) * | 2004-07-20 | 2004-08-25 | Avecia Ltd | Manufacturing process |
| JP4533303B2 (ja) * | 2004-12-03 | 2010-09-01 | キヤノン株式会社 | アゾ顔料分散体の製造方法 |
| DE602005025919D1 (de) * | 2004-12-03 | 2011-02-24 | Canon Kk | Herstellungsverfahren für azopigmentdispersion |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7240687A (en) * | 1986-05-03 | 1987-11-05 | Hoechst Aktiengesellschaft | Process for making azo pigments |
Family Cites Families (5)
| 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 |
| DE1085278B (de) * | 1958-03-08 | 1960-07-14 | Hoechst Ag | Verfahren zur kontinuierlichen Herstellung von Azopigmenten |
| DE2629076B2 (de) * | 1976-06-29 | 1978-04-27 | Basf Farben + Fasern Ag, 2000 Hamburg | Verfahren zur Herstellung eines Disazopigmentes mit verbesserten anwendungstechnischen Eigenschaften |
| 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 |
-
1987
- 1987-03-26 IN IN220/MAS/87A patent/IN169308B/en unknown
- 1987-04-18 EP EP87105766A patent/EP0244687B1/de not_active Expired - Lifetime
- 1987-04-18 ES ES198787105766T patent/ES2037023T3/es not_active Expired - Lifetime
- 1987-04-18 DE DE8787105766T patent/DE3782966D1/de not_active Expired - Lifetime
- 1987-05-01 DK DK223487A patent/DK168394B1/da not_active IP Right Cessation
- 1987-05-01 AU AU72407/87A patent/AU594760B2/en not_active Ceased
- 1987-05-01 KR KR1019870004280A patent/KR960008248B1/ko not_active Expired - Fee Related
- 1987-05-06 JP JP62109069A patent/JPH0784566B2/ja not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7240687A (en) * | 1986-05-03 | 1987-11-05 | Hoechst Aktiengesellschaft | Process for making azo pigments |
Also Published As
| Publication number | Publication date |
|---|---|
| DK223487D0 (da) | 1987-05-01 |
| JPH0784566B2 (ja) | 1995-09-13 |
| ES2037023T3 (es) | 1993-06-16 |
| EP0244687B1 (de) | 1992-12-09 |
| EP0244687A2 (de) | 1987-11-11 |
| AU7240787A (en) | 1987-11-05 |
| KR960008248B1 (ko) | 1996-06-21 |
| IN169308B (enrdf_load_stackoverflow) | 1991-09-28 |
| KR870011207A (ko) | 1987-12-21 |
| DK223487A (da) | 1987-11-04 |
| EP0244687A3 (en) | 1990-11-14 |
| JPS62263261A (ja) | 1987-11-16 |
| DE3782966D1 (de) | 1993-01-21 |
| DK168394B1 (da) | 1994-03-21 |
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