DE1067157B - Process for the preparation of a dye - Google Patents
Process for the preparation of a dyeInfo
- Publication number
- DE1067157B DE1067157B DE1956F0019858 DEF0019858A DE1067157B DE 1067157 B DE1067157 B DE 1067157B DE 1956F0019858 DE1956F0019858 DE 1956F0019858 DE F0019858 A DEF0019858 A DE F0019858A DE 1067157 B DE1067157 B DE 1067157B
- Authority
- DE
- Germany
- Prior art keywords
- dye
- amino
- perylene
- dimethylbenzene
- tetracarboxylic acid
- 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
- 238000000034 method Methods 0.000 title claims description 4
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 claims description 6
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 4
- 239000004800 polyvinyl chloride Substances 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 239000000976 ink Substances 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 2
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 2
- 230000000740 bleeding effect Effects 0.000 description 2
- JLNMBIKJQAKQBH-UHFFFAOYSA-N 4-cyclohexylaniline Chemical compound C1=CC(N)=CC=C1C1CCCCC1 JLNMBIKJQAKQBH-UHFFFAOYSA-N 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- AIOLRLMFOWGSPL-UHFFFAOYSA-N chembl1337820 Chemical compound C1=CC=C2C(N=NC3=C4C=CC(=CC4=CC(=C3O)S(O)(=O)=O)S(O)(=O)=O)=CC=CC2=C1 AIOLRLMFOWGSPL-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
DEUTSCHESGERMAN
Gegenstand der Patentanmeldung F 19790 IVb/22e ist ein Verfahren zur Herstellung eines Farbstoffes, der sich in vorteilhafter Weise zum Färben von weichmacherhaltigem Polyvinylchlorid sowie für Lacke und Druckfarben in sehr guten Echtheitseigenschaften eignet, welches darin besteht, daß man Perylen-3,4,9,10-tetracarbonsäure oder ihr Anhydrid mit p-Cyclohexylanilin kondensiert.The subject of patent application F 19790 IVb / 22e is a process for the production of a dye, which is advantageous for dyeing plasticized polyvinyl chloride and for paints and Printing inks with very good fastness properties are suitable, which consists in using perylene-3,4,9,10-tetracarboxylic acid or their anhydride condensed with p-cyclohexylaniline.
In Erweiterung dieses Erfindungsgegenstandes wurde nun gefunden, daß man einen Farbstoff von ähnlich ausgezeichneten Eigenschaften erhält, wenn man Perylen-3,4,9,10-tetracarbonsäure oder ihr Anhydrid mit l-Amino-3,5-dimethylbenzol umsetzt. Diese Tatsache ist um so überraschender, als die Kondensationsprodukte von Perylen-tetracarbonsäure mit dem isomeren l-Amino-2,6-dimethylbenzol oder mit dem t-Amino-2,4-dimethylbenzol schlechte Echtheitseigenschaften besitzen.As an extension of this subject matter of the invention, it has now been found that a dye of similarly excellent properties are obtained when perylene-3,4,9,10-tetracarboxylic acid or its anhydride is used reacted with l-amino-3,5-dimethylbenzene. This fact is all the more surprising as the condensation products of perylene tetracarboxylic acid with the isomeric l-amino-2,6-dimethylbenzene or with the t-amino-2,4-dimethylbenzene have poor fastness properties.
Der neue Farbstoff eignet sich sehr gut als Pigment in der Druckfarben- und Lackindustrie, zum Echtfärben von weichmacherhaltigem Polyvinylchlorid, ferner in sogenannten Einbrennlacken oder zum'Färben in der Spinnmasse.The new dye is very suitable as a pigment in the printing inks and coatings industry, for Fast dyeing of plasticized polyvinyl chloride, also in so-called stoving enamels or for dyeing in the spinning mass.
Dem aus der schweizerischen Patentschrift 105 852 bekannten Farbstoff aus der Perylen-tetracarbonsäure u id l-Amino-2-methylbenzol ist der neue Farbstoff ir der Hitzebeständigkeit der Polyvinylchloridfärbungen und in der Ausblutechtheit in Polyvinylchlorid wesentlich überlegen.The perylene tetracarboxylic acid dye known from Swiss patent specification 105 852 u id l-amino-2-methylbenzene is the new dye ir the heat resistance of the polyvinyl chloride dyeings and the resistance to bleeding in polyvinyl chloride substantially superior.
In 200 Gewichtsteile l-Amino-3,5-dimethylbenzol werden nacheinander unter Rühren 20 Gewichtsteile Perylen-S^^.lO-tetracarbonsäure-dianhydrid und 10 Volumteile konzentrierte Salzsäure eingetragen. Das Gemisch wird 12 Stunden auf 210 bis 220° C erhitzt unter kontinuierlichem Abdestillieren des Wassers. Das Produkt wird kalt abgesaugt, ein bis zweimal mir Methanol gewaschen, mehrere Male mit verdünnter Natronlauge ausgekocht, mit heißem Wasser neutral gewaschen und getrocknet.In 200 parts by weight of 1-amino-3,5-dimethylbenzene, 20 parts by weight are successively added with stirring Perylene-S ^^. LO-tetracarboxylic acid dianhydride and 10 Parts by volume of concentrated hydrochloric acid entered. The mixture is heated to 210-220 ° C. for 12 hours with continuous distilling off of the water. The product is filtered off with cold suction, once or twice Washed with methanol, boiled several times with dilute sodium hydroxide solution, with hot water washed neutral and dried.
Der aus Chinolin in kurzen Prismen kristallisielende
rote Farbstoff schmilzt nicht bis 300° C, ist in den üblichen organischen Lösungsmitteln schwer
löslich und löst sich in konzentrierter Schwefelsäure mit violett- bis bordoroter Farbe ohne Fluoreszenz.
Er zeichnet sich durch eine außergewöhnliche Klarheit und hervorragende Echtheitseigenschaften sowohl
Verfahren zur Herstellung
eines FarbstoffesThe red dye, which crystallizes from quinoline in short prisms, does not melt up to 300 ° C, is sparingly soluble in the usual organic solvents and dissolves in concentrated sulfuric acid with a violet to Bordeaux red color without fluorescence. It is characterized by an exceptional clarity and excellent fastness properties both method of manufacture
of a dye
Anmelder:Applicant:
Farbwerke Hoechst AktiengesellschaftFarbwerke Hoechst Aktiengesellschaft
vormals Meister Lucius & Brüning,formerly Master Lucius & Brüning,
Frankfurt/M., Brüningstr. 45Frankfurt / M., Brüningstr. 45
Dr. Wilhelm Eckert, Frankfurt/M. -Unterliederbach,Dr. Wilhelm Eckert, Frankfurt / M. -Unterliederbach,
und Dr. Hermann Remy, Neu Isenburg,and Dr. Hermann Remy, Neu Isenburg,
sind als Erfinder genannt wordenhave been named as inventors
in Lacken als auch in Polyvinylchloridmischungen aus und besitzt eine sehr gute ölechtheit, Überspritzechtheit, Lösungsmittelechtheit, Ausblutechtheit und Lichtechtheit. in lacquers as well as in polyvinyl chloride mixtures and has a very good oiliness, overspray fastness, Fastness to solvents, fastness to bleeding and fastness to light.
In 400 Volumteile Chinolin werden nacheinander unter Rühren 20 Gewichtsteile Perylen-3,4,9,10-tetracarbonsäure-dianhydrid, 35 Gewichtsteile 1-Amino-3,5-dimethylbenzol und 10 Volumteile konzentrierte Salzsäure eingetragen. Das Gemisch wird 14 Stunden auf 200 bis 210° C erhitzt unter kontinuierlichem Abdestülieren des Wassers. Dann wird das Produkt kalt abgesaugt und nach den Angaben des Beispiels 1 aufgearbeitet. Der erhaltene Farbstoff ist identisch mit dem nach Beispiel 1 erhaltenen Produkt.In 400 parts by volume of quinoline, 20 parts by weight of perylene-3,4,9,10-tetracarboxylic acid dianhydride, 35 parts by weight of 1-amino-3,5-dimethylbenzene and 10 parts by volume of concentrated hydrochloric acid entered. The mixture is 14 hours heated to 200 to 210 ° C while continuously distilling off the water. Then the product Sucked off cold with suction and worked up according to the information in Example 1. The dye obtained is identical with the product obtained according to Example 1.
eines Farbstoffes, von weichmacherhaltigemof a dye, of plasticized
HerstellungManufacturing
Claims (1)
Schweizerische Patentschrift Nr. 105 852.Considered publications:
Swiss patent specification No. 105 852.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1956F0019858 DE1067157B (en) | 1956-03-22 | 1956-03-22 | Process for the preparation of a dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1956F0019858 DE1067157B (en) | 1956-03-22 | 1956-03-22 | Process for the preparation of a dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1067157B true DE1067157B (en) | 1959-10-15 |
Family
ID=593098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1956F0019858 Pending DE1067157B (en) | 1956-03-22 | 1956-03-22 | Process for the preparation of a dye |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1067157B (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1257096B (en) * | 1962-08-16 | 1967-12-28 | Basf Ag | Use of two new modifications of perylene-3, 4, 9, 10-tetracarboxylic acid-bis- (4-phenylazo) -phenylimide as pigments |
| EP0023191A1 (en) * | 1979-07-04 | 1981-01-28 | Ciba-Geigy Ag | Modification of perylene-tetracarboxylic acid bis (3,5-dimethylphenyl) imide, its preparation and use in pigmentation |
| EP0042819A1 (en) * | 1980-06-23 | 1981-12-30 | Ciba-Geigy Ag | Process for the preparation of opaque perylene-tetracarboxylic-bis-(3,5-dimethylphenyl imide) |
| EP0176902A3 (en) * | 1984-10-03 | 1989-10-25 | Hoechst Aktiengesellschaft | Mixed crystals of pigments on the basis of diimides of perylene tetracarboxylic acid, their manufacturing process and their use |
| EP0176899A3 (en) * | 1984-10-03 | 1989-10-25 | Hoechst Aktiengesellschaft | Mixed crystals of pigments on the basis of diimides of perylene tetracarboxylic acid, their manufacturing process and their use |
| EP0176900A3 (en) * | 1984-10-03 | 1989-10-25 | Hoechst Aktiengesellschaft | Process for the manufacture of mixed crystals of pigments on the basis of diimides of perylene tetracarboxylic acid, and their use |
| US5264034A (en) * | 1989-08-11 | 1993-11-23 | Hoechst Aktiengesellschaft | Pigment preparations based on perylene compounds |
| US5626662A (en) * | 1994-04-21 | 1997-05-06 | Hoechst Aktiengesellschaft | Fine division in the preparation of organic pigments |
| US5958129A (en) * | 1997-03-10 | 1999-09-28 | Clariant Gmbh | Pigment formulations and processes for their preparation |
| US7056378B2 (en) | 2002-04-16 | 2006-06-06 | Clariant Gmbh | Method for producing vattable organic pigments |
| WO2009074504A3 (en) * | 2007-12-10 | 2009-12-30 | Basf Se | Synthesis of dyes in mixing units |
-
1956
- 1956-03-22 DE DE1956F0019858 patent/DE1067157B/en active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1257096B (en) * | 1962-08-16 | 1967-12-28 | Basf Ag | Use of two new modifications of perylene-3, 4, 9, 10-tetracarboxylic acid-bis- (4-phenylazo) -phenylimide as pigments |
| EP0023191A1 (en) * | 1979-07-04 | 1981-01-28 | Ciba-Geigy Ag | Modification of perylene-tetracarboxylic acid bis (3,5-dimethylphenyl) imide, its preparation and use in pigmentation |
| US4404385A (en) | 1979-07-04 | 1983-09-13 | Ciba-Geigy Corporation | Novel modification of perylenetetracarboxylic acid-bis-(3,5-dimethylphenyl)imide |
| EP0042819A1 (en) * | 1980-06-23 | 1981-12-30 | Ciba-Geigy Ag | Process for the preparation of opaque perylene-tetracarboxylic-bis-(3,5-dimethylphenyl imide) |
| EP0176900A3 (en) * | 1984-10-03 | 1989-10-25 | Hoechst Aktiengesellschaft | Process for the manufacture of mixed crystals of pigments on the basis of diimides of perylene tetracarboxylic acid, and their use |
| EP0176899A3 (en) * | 1984-10-03 | 1989-10-25 | Hoechst Aktiengesellschaft | Mixed crystals of pigments on the basis of diimides of perylene tetracarboxylic acid, their manufacturing process and their use |
| EP0176902A3 (en) * | 1984-10-03 | 1989-10-25 | Hoechst Aktiengesellschaft | Mixed crystals of pigments on the basis of diimides of perylene tetracarboxylic acid, their manufacturing process and their use |
| US5264034A (en) * | 1989-08-11 | 1993-11-23 | Hoechst Aktiengesellschaft | Pigment preparations based on perylene compounds |
| US5626662A (en) * | 1994-04-21 | 1997-05-06 | Hoechst Aktiengesellschaft | Fine division in the preparation of organic pigments |
| US5958129A (en) * | 1997-03-10 | 1999-09-28 | Clariant Gmbh | Pigment formulations and processes for their preparation |
| US7056378B2 (en) | 2002-04-16 | 2006-06-06 | Clariant Gmbh | Method for producing vattable organic pigments |
| WO2009074504A3 (en) * | 2007-12-10 | 2009-12-30 | Basf Se | Synthesis of dyes in mixing units |
| US8551237B2 (en) | 2007-12-10 | 2013-10-08 | Basf Se | Synthesis of colorants in mixing apparatus |
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