DE2011018A1 - Azo dye - Google Patents
Azo dyeInfo
- Publication number
- DE2011018A1 DE2011018A1 DE19702011018 DE2011018A DE2011018A1 DE 2011018 A1 DE2011018 A1 DE 2011018A1 DE 19702011018 DE19702011018 DE 19702011018 DE 2011018 A DE2011018 A DE 2011018A DE 2011018 A1 DE2011018 A1 DE 2011018A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- pigment
- azo dye
- dye
- red
- 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.)
- Pending
Links
- 239000000987 azo dye Substances 0.000 title claims description 5
- 239000000049 pigment Substances 0.000 claims description 9
- 239000000975 dye Substances 0.000 claims description 7
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- GHQCIALFYKYZGS-UHFFFAOYSA-N dibenzofuran-3-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3OC2=C1 GHQCIALFYKYZGS-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- QCHIESZMDORMPC-UHFFFAOYSA-N dibutyltin;hexyl 2-hydroxyethanedithioate Chemical compound CCCC[Sn]CCCC.CCCCCCSC(=S)CO QCHIESZMDORMPC-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000007644 letterpress printing Methods 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 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
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002966 varnish 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/3634—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized heterocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
Badische Anilin- & Soda-Fabrik AG ~ ' .Badische Anilin- & Soda-Fabrik AG ~ ' .
Unsere Zeichen: O..Z. 26 660 Hee/Fe 6700 Ludwigshafen, den. 6.3.197OOur symbols: O..Z. 26 660 Hee / Fe 6700 Ludwigshafen, the. 6.3.197O
AiZ ο färbst off
Diese Erfindung "betrifft den neuen Azofarbstoff der Formel AiZ ο stains off
This invention "relates to the new azo dye of the formula
seine Herstellung und Verwendung als Pigmentfarbstoff. M its manufacture and use as a pigment. M.
Der neue Farbstoff wird auf an sich übliche Weise durch Di-.azotieren von 3-Aminodibenzofuran und Kuppeln der Diazoniumverbindung auf 2,6-Dihydroxy-3-oyan-4-methylpyridin hergestellt. Es ist ein brillanter, gelbstichig röter Pigmentfärbst off, der eine sehr gute Lichtechtheit aufweist und überraschend ausgiebige Färbungen ergibt. Beispielsweise ist seine Farbstärke etwa doppelt so hoch wie entsprechende Färbungen, die man unter Verwendung des handelsüblichen, aber schlechter lichtechten Pigmentfarbstoffea· Lake Red 0 (C. I. Pigment Red. 53, Colour Index No/ 15 585) erhält.The new dye is disazotized in a conventional manner of 3-aminodibenzofuran and coupling of the diazonium compound on 2,6-dihydroxy-3-oyan-4-methylpyridine. It is a brilliant, yellowish red pigment color off, which has very good lightfastness and surprisingly extensive coloration. For example, his Color strength about twice as high as corresponding colorations, the one using the commercial, but worse lightfast pigment dyes a Lake Red 0 (C. I. Pigment Red. 53, Color Index No / 15 585).
Aufgrund dieser vorteilhaften Eigenschaften ist der neue rote s| Azofarbstoff insbesondere als Pigmentfarbstoff geeignet. So läßt er sicji für alle Bereiche der Pigmenttechnik verwenden, beispielsweise für die Herstellung von Druckfarben oder Lackfarben» für die Massefärbung von Kunststoffen sowie für die Spinnfärbung«Because of these beneficial properties, the new red s | Azo dye particularly suitable as a pigment dye. So he lets sicji be used for all areas of pigment technology, for example for the production of printing inks or lacquer colors »for the mass coloring of plastics as well as for the Spin dyeing "
Die in den Beispielen genannten Teile sind Gewichtsteile. verhalten sich zu Gewichtsteilen wie das Liter zumThe parts mentioned in the examples are parts by weight. relate to parts by weight like the liter to
Kilogramm.Kilogram.
706/69 109839/H4Q 706/69 109839 / H4Q
-2- O.ζ. 26 660-2- O.ζ. 26 660
Beispiel 1 Herstellung:example 1 Manufacturing:
18,3 Teile 3-Aminodibenzofuran werden mit 100 Raumteilen 3-normaler Salzsäure und 200 Teilen Eis in Lösung gebracht. Man tropft 55 Raumteile einer 2-normalen Lösung von Natriumnitrit in Wasser ein und rührt 2 Stunden. Die dabei erhaltene Lösung wird in eine Suspension von 15 Teilen 2,6-Dihydroxy-3-cyan-4-methylpyridin in 300 Raumteilen Wasser eingetropft. Schließlich wird durch Zutropfen einer wässrigen Natriumacetatlösung ein pH-Wert von 5 bis 6 eingestellt und 6 Stunden gerührt. Der Farbstoff wird abgesaugt, mit Wasser gründlich gewaschen und getrocknet. Man erhält 32 Teile eines leuchtend roten Pigmentpulvers.18.3 parts of 3-aminodibenzofuran are brought into solution with 100 parts by volume of 3 normal hydrochloric acid and 200 parts of ice. 55 parts by volume of a 2 normal solution of sodium nitrite in water are added dropwise and the mixture is stirred for 2 hours. The received Solution is in a suspension of 15 parts of 2,6-dihydroxy-3-cyano-4-methylpyridine dripped into 300 parts by volume of water. Finally, an aqueous sodium acetate solution is added dropwise adjusted to a pH of 5 to 6 and stirred for 6 hours. The dye is suctioned off, rinsed with water thoroughly washed and dried. 32 parts of a bright red pigment powder are obtained.
Beispiel 2 Verwendung:Example 2 Use:
a) In Druckfarben: 1 Teil des nach Beispiel 1 hergestellten Pigmentfärbstoffes wird mit 20 Teilen Leinölfirnis auf dem Dreiwalzenstuhl verrieben. Die so hergestellte Druckfarbe gibt bei Verwendung im Buchdruck sehr farbtiefe, brillante gelbstichig-rote Färbungen, die sehr gute Lichtechtheit aufweisen.a) In printing inks: 1 part of the pigment dye prepared according to Example 1 is rubbed with 20 parts of linseed oil varnish on a three-roller mill. When used in letterpress printing, the printing ink produced in this way gives very deep, brilliant yellow-tinged red colorations which have very good lightfastness.
b) Im Lack: 2 Teile des nach Beispiel 1 hergestellten Pigmentes werden mit 98 Teilen Nitrostammlack im Atritor dispergiert. Der Nitrostammlack wurde durch Mischen von 19 Teilen Nitrocellulose butanolfeucht, 4 Teilen eines durch alkalische Kondensation von 85 Teilen Methylcyclohexanon und 15 Teilen Cyclohexanon erhältlichen Harzes, 4,7 Teilen Phthalsäuredibutylester, 4 Teilen Phthalsäurebutylbenzylphthalat, 30 Teilen Butylacetat, 10 Teilen Essigester und 29,3 Teilen Toluol hergestellt. Der gefärbte Nitrolack wird auf Bleche gespritzt und luftgetrocknet. Man erhält eine brillante gelbstichigrote Lackierung von sehr guter Liohtechtheit. b) In the paint: 2 parts of the pigment prepared according to Example 1 are dispersed with 98 parts of nitrous base paint in the atritor. The nitrostammlack was wet by mixing 19 parts of nitrocellulose butanol, 4 parts of a resin obtainable by alkaline condensation of 85 parts of methylcyclohexanone and 15 parts of cyclohexanone, 4.7 parts of dibutyl phthalate, 4 parts of butylbenzyl phthalate, 30 parts of butyl acetate, 10 parts of ethyl acetate and 29.3 parts Toluene produced. The colored nitro lacquer is sprayed onto metal sheets and air-dried. A brilliant yellow-tinged red paintwork of very good lightfastness is obtained.
c) In Kunststoffen: 1 Teil eines nach Beispiel 1 hergestellten Pigmentes wird in 500 Teile Polyvinylchloridpulver und 10 Teilen eines Stabilisators, der aus 7,5 Teilen Dibutylzinnbis-thioglykolsäurehexylester und 2,5 Teilen Dioctylphthalatc) In plastics: 1 part of a pigment prepared according to Example 1 is dissolved in 500 parts of polyvinyl chloride powder and 10 parts of a stabilizer composed of 7.5 parts of dibutyltin bis-thioglycolic acid hexyl ester and 2.5 parts of dioctyl phthalate
109839/U40 ' -3-109839 / U40 '-3-
-3- O,Z. 26 660-3- O, Z. 26 660
besteht, auf einem heizbaren Mischwalzwerk eingearbeitet.. Man erhält ein in leuchtend rotem Farbton gefärbtes Hart-Polyvinylchlorid, das sehr gute Lichtechtheit aufweist.consists, incorporated on a heatable mixing mill. A hard polyvinyl chloride colored in a bright red shade is obtained, which has very good lightfastness.
109839/U AO ~4~109839 / U AO ~ 4 ~
Claims (3)
1. Der Azofarbstoff der Formel Claims
1. The azo dye of the formula
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702011018 DE2011018A1 (en) | 1970-03-09 | 1970-03-09 | Azo dye |
| CH209671A CH548442A (en) | 1970-03-09 | 1971-02-12 | METHOD OF MANUFACTURING AN AZO DYE. |
| FR7107685A FR2081785B3 (en) | 1970-03-09 | 1971-03-05 | |
| GB2336271A GB1306190A (en) | 1970-03-09 | 1971-04-19 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702011018 DE2011018A1 (en) | 1970-03-09 | 1970-03-09 | Azo dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2011018A1 true DE2011018A1 (en) | 1971-09-23 |
Family
ID=5764528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702011018 Pending DE2011018A1 (en) | 1970-03-09 | 1970-03-09 | Azo dye |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH548442A (en) |
| DE (1) | DE2011018A1 (en) |
| FR (1) | FR2081785B3 (en) |
| GB (1) | GB1306190A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3936437A (en) * | 1972-12-22 | 1976-02-03 | Imperial Chemical Industries Limited | Monoazo compounds derived from 2-hydroxymethyl-amino benzoic acids and 2,6-dihydroxypyridines |
-
1970
- 1970-03-09 DE DE19702011018 patent/DE2011018A1/en active Pending
-
1971
- 1971-02-12 CH CH209671A patent/CH548442A/en not_active IP Right Cessation
- 1971-03-05 FR FR7107685A patent/FR2081785B3/fr not_active Expired
- 1971-04-19 GB GB2336271A patent/GB1306190A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3936437A (en) * | 1972-12-22 | 1976-02-03 | Imperial Chemical Industries Limited | Monoazo compounds derived from 2-hydroxymethyl-amino benzoic acids and 2,6-dihydroxypyridines |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2081785A7 (en) | 1971-12-10 |
| CH548442A (en) | 1974-04-30 |
| GB1306190A (en) | 1973-02-07 |
| FR2081785B3 (en) | 1973-12-28 |
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