DE1067952B - Process for the preparation of a dye - Google Patents
Process for the preparation of a dyeInfo
- Publication number
- DE1067952B DE1067952B DENDAT1067952D DE1067952DA DE1067952B DE 1067952 B DE1067952 B DE 1067952B DE NDAT1067952 D DENDAT1067952 D DE NDAT1067952D DE 1067952D A DE1067952D A DE 1067952DA DE 1067952 B DE1067952 B DE 1067952B
- Authority
- DE
- Germany
- Prior art keywords
- dye
- dichloroaniline
- polyvinyl chloride
- parts
- perylene
- 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
- 238000002360 preparation method Methods 0.000 title description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 7
- 239000004800 polyvinyl chloride Substances 0.000 claims description 7
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 238000004043 dyeing Methods 0.000 claims description 3
- 239000000976 ink Substances 0.000 claims description 3
- 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 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims 1
- 238000010186 staining Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 206010018987 Haemorrhage Diseases 0.000 description 2
- 230000000740 bleeding Effects 0.000 description 2
- 231100000319 bleeding Toxicity 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical compound NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 1
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-Chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- JLNMBIKJQAKQBH-UHFFFAOYSA-N 4-cyclohexylaniline Chemical compound C1=CC(N)=CC=C1C1CCCCC1 JLNMBIKJQAKQBH-UHFFFAOYSA-N 0.000 description 1
- 210000003298 Dental Enamel Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 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
Description
Verfahren zur Herstellung eines Farbstoffes Gegenstand der Patentanmeldung F 19790 IV b/22 e 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-Cyclohexyl-anilin kondensiert.Process for the preparation of a dye the subject of the patent application F 19790 IV b / 22 e is a process for the production of a dye, which advantageously for dyeing plasticized polyvinyl chloride as well suitable for lacquers and printing inks with very good fastness properties, which in it consists that perylene-3,4,9,10-tetracarboxylic acid or its anhydride with p-cyclohexyl-aniline condensed.
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 3,4-Dichloranilin umsetzt.As an extension of this subject matter of the invention it has now been found that a dye with similarly excellent properties is obtained by using perylene-3,4,9,10-tetracarboxylic acid or its anhydride is reacted with 3,4-dichloroaniline.
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 printing inks and lacquer industry, for the real coloring of plasticized polyvinyl chloride, furthermore in so-called stoving enamels or for dyeing in the spinning mass.
Gegenüber den Farbstoffen, die durch Umsetzen der Perylentetracarbonsäure oder ihres Anhydrids mit 2,5-Dichloranilin oder 3,5-Dichloranilin erhalten werden, zeichnet sich der erfindungsgemäße Farbstoff durch eine bessere Lichtechtheit aus. Ferner ist der neue Farbstoff den Farbstoffen aus der Perylentetracarbonsäure und 2,3-Dichloranilin, 2,4-Dichloranilin sowie 2,6-Dichloranilin in der Ausblutechtheit in Polyvinylchlorid und dem aus der schweizerischen Patentschrift 101757 bekannten Farbstoff aus der Perylentetracarbonsäure und 4-Chloranilin in der Hitzebeständigkeit der Polyvinylchloridfärbungen wesentlich überlegen.Compared to the dyes obtained by reacting the perylenetetracarboxylic acid or its anhydride with 2,5-dichloroaniline or 3,5-dichloroaniline, the dye according to the invention is distinguished by better lightfastness. Furthermore, the new dye is the dyes from the perylenetetracarboxylic acid and 2,3-dichloroaniline, 2,4-dichloroaniline and 2,6-dichloroaniline in the bleeding resistance in polyvinyl chloride and from the Swiss patent 101757 known from the dye from the perylenetetracarboxylic acid and 4-chloroaniline in significantly superior to the heat resistance of polyvinyl chloride dyeings.
Beispiel 1 In 400 Volumteile Chinolin werden nacheinander unter Rühren 20 Gewichtsteile Perylen-3,4,9,10-tetracarbonsäuredianhydrid, 48 Gewichtsteile 3,4-Dichloranilin und 10 Volumteile konzentrierte Salzsäure eingetragen. Das Gemisch wird 15 Stunden auf 200° C erhitzt unter kontinuierlichem Abdestilheren des Wassers. Das Produkt wird kalt abgesaugt, einige Male mit Methanol gewaschen, mit verdünnter Natronlauge ausgekocht, mit heißem Wasser neutral gewaschen und getrocknet.Example 1 In 400 parts by volume of quinoline are added successively with stirring 20 parts by weight of perylene-3,4,9,10-tetracarboxylic acid dianhydride, 48 parts by weight of 3,4-dichloroaniline and 10 parts by volume of concentrated hydrochloric acid entered. The mixture is 15 hours heated to 200 ° C with continuous distillation of the water. The product is filtered off with suction while cold, washed a few times with methanol, with dilute sodium hydroxide solution boiled, washed neutral with hot water and dried.
Der in den üblichen organischen Lösungsmitteln schwerlösliche rote Farbstoff schmilzt nicht bis 300° C und löst sich in konzentrierter Schwefelsäure mit violetter Farbe ohne Fluoreszenz. Er zeichnet sich durch besondere Klarheit und hervorragende Echtheitseigenschaften sowohl in Lacken als auch in Polyvinylchloridmischungen aus und besitzt eine sehr gute Ölechtheit, Überspritzechtheit, Lösungsmittelechtheit, Ausblutechtheit und Lichtechtheit. Lacke und Polyvinylchlorid werden in blaustichigroten Tönen gefärbt.The red one, which is sparingly soluble in the usual organic solvents Dye does not melt up to 300 ° C and dissolves in concentrated sulfuric acid with purple color without fluorescence. It is characterized by particular clarity and excellent fastness properties both in lacquers and in polyvinyl chloride blends and has a very good oil quality, overspray fastness, solvent fastness, Fastness to bleeding and fastness to light. Lacquers and polyvinyl chloride turn blue-tinged red Tones colored.
Beispiel 2 In einen Rührautoklav werden in 320 Gewichtsteile Wasser nacheinander 20 Gewichtsteile Perylen-3,4,9,10-tetracarbonsäure-dianhydrid, 50 Gewichtsteile 3,4-Dichloranilin und 10 Volumteile konzentrierte Salzsäure eingetragen. Das Gemisch wird bei 210 bis 220° C und 40 Atmosphären Druck 12 Stunden gerührt. 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.Example 2 In a stirred autoclave in 320 parts by weight of water successively 20 parts by weight of perylene-3,4,9,10-tetracarboxylic acid dianhydride, 50 parts by weight 3,4-dichloroaniline and 10 parts by volume of concentrated hydrochloric acid entered. The mixture is stirred at 210 to 220 ° C and 40 atmospheric pressure for 12 hours. Then that will Product is filtered off with suction while cold and worked up as described in Example 1. The received The dye is identical to the product obtained in Example 1.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1067952B true DE1067952B (en) | 1959-10-29 |
Family
ID=593372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1067952D Pending DE1067952B (en) | Process for the preparation of a dye |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1067952B (en) |
Cited By (2)
| 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 |
| WO2009074504A3 (en) * | 2007-12-10 | 2009-12-30 | Basf Se | Synthesis of dyes in mixing units |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH101757A (en) * | 1923-01-03 | 1923-10-16 | Kalle & Co Ag | Process for the preparation of a vat dye. |
| US2543747A (en) * | 1948-08-27 | 1951-03-06 | Gen Aniline & Film Corp | Preparation of n.n'-diaryl derivatives of perylene diimid |
-
0
- DE DENDAT1067952D patent/DE1067952B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH101757A (en) * | 1923-01-03 | 1923-10-16 | Kalle & Co Ag | Process for the preparation of a vat dye. |
| US2543747A (en) * | 1948-08-27 | 1951-03-06 | Gen Aniline & Film Corp | Preparation of n.n'-diaryl derivatives of perylene diimid |
Cited By (3)
| 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 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1067157B (en) | Process for the preparation of a dye | |
| DE1105085B (en) | Process for the preparation of a dye | |
| DE1067952B (en) | Process for the preparation of a dye | |
| DE1094897B (en) | Process for producing a pigment | |
| DE1067953B (en) | Process for the preparation of a dye | |
| CH469789A (en) | Process for the preparation of naphth- (2,3-b-) indolizine-6,11-dione-12-carboxylic acid phenylamide pigments | |
| DE1067951B (en) | Process for the preparation of a dye | |
| DE1113773B (en) | Process for the preparation of a dye | |
| DE1067548B (en) | Process for the preparation of a dye | |
| DE1069797B (en) | Process for the preparation of a dye | |
| DE2361433C2 (en) | Poorly soluble disazo compounds, their preparation and use | |
| DE1130099B (en) | Process for the production of fluorescent dyes | |
| DE1070317B (en) | Process for the preparation of a dye | |
| DE1055156B (en) | Process for the preparation of a dye | |
| CH351059A (en) | Process for the production of dyes | |
| DE2063714B2 (en) | ||
| CH351058A (en) | Process for the production of dyes | |
| DE1105084B (en) | Process for the preparation of a dye | |
| CH351056A (en) | Process for the production of dyes | |
| DE2116048C3 (en) | Dye of the perylenetetracarboxylic diimide series | |
| CH351061A (en) | Process for the preparation of a dye | |
| DE1132272B (en) | Process for producing a pigment | |
| CH351055A (en) | Process for the production of dyes | |
| CH351057A (en) | Process for the production of dyes | |
| DE614838C (en) | Process for the preparation of water-insoluble disazo dyes |