CH351056A - Process for the production of dyes - Google Patents
Process for the production of dyesInfo
- Publication number
- CH351056A CH351056A CH351056DA CH351056A CH 351056 A CH351056 A CH 351056A CH 351056D A CH351056D A CH 351056DA CH 351056 A CH351056 A CH 351056A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- dyes
- parts
- perylene
- fastness
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 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 5
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 239000000976 ink Substances 0.000 claims description 2
- -1 polyethylene Polymers 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims 1
- 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
- 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
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- JLNMBIKJQAKQBH-UHFFFAOYSA-N 4-cyclohexylaniline Chemical compound C1=CC(N)=CC=C1C1CCCCC1 JLNMBIKJQAKQBH-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 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
- 239000004014 plasticizer 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)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
Verfahren zur Herstellung von Farbstoffen Gegenstand des Hauptpatents ist ein Verfahren zur Herstellung von Farbstoffen, die sich in vorteil hafter Weise zum Färben von Kunststoffen, wie weichmacherhaltigem Polyvinylchlorid oder Polyäthy len, oder Lacken und zur Herstellung von Druck farben mit sehr guten Echtheitseigenschaften eignen, welches dadurch gekennzeichnet ist, dass man Pery- len-3,4,9,10-tetracarbonsäure oder ihr Anhydrid mit p-Cyclohexyl-anilin kondensiert.
Es wurde nun gefunden, dass man einen Farbstoff mit ähnlich ausgezeichneten Eigenschaften erhält, wenn man Perylen-3,4,9,10-tetracarbonsäure oder ihr Anhydrid mit p-Isopropylanilin umsetzt.
Der neue Farbstoff eignet sich sehr gut als Pig ment in der Druckfarben- und Lackindustrie, zum Echtfärben von Kunststoffen, wie weichmacherhalti- gem Polyvinylchlorid oder Polyäthylen, ferner in so genannten Einbrennlacken oder zum Färben in der Spinnmasse.
<I>Beispiel 1</I> In 200 Volumteile p-Isopropyl-anilin werden nacheinander unter Rühren 30 Gewichtsteile Pery- len-3,4,9,10-tetracarbonsäure-dianhydrid und 20 Vo- lumteile konzentrierte Salzsäure eingetragen. Das Gemisch wird 12 Stunden auf 210-220 C erhitzt unter kontinuierlichem Abdestillieren des Wassers. Das Produkt wird kalt abgesaugt, einige Male mit Methanol gewaschen, mehrere Male mit verdünnter Natronlauge ausgekocht, mit heissem Wasser neutral gewaschen und getrocknet.
Der aus Chinolin in feinen Nadeln kristallisie rende rote Farbstoff schmilzt nicht bis 300 C, ist in den üblichen organischen Lösungsmitteln schwer lös lich und löst sich in konzentrierter Schwefelsäure mit violetter Farbe ohne Fluoreszenz. Er zeichnet sich durch eine auffallende Klarheit und hervorragende Echtheitseigenschaften sowohl. in Lacken als auch in Kunststoffen, wie z. B. Polyvinylchlorid-Mischungen, aus und besitzt eine sehr gute ölechtheit, Überspritz- echtheit, Lösungsmittelechtheit, Ausblutechtheit und Lichtechtheit.
<I>Beispiel 2</I> In 210 Volumteile Chinolin werden nacheinander unter Rühren 30 Gewichtsteile Perylen-3,4,9,10-tetra- carbonsäure-dianhydrid, 23 Gewichtsteile p-Isopro- pyl-anilin und 15 Volumteile konzentrierte Salzsäure eingetragen. Das Gemisch wird 15 Stunden auf 200 bis 210 C erhitzt unter kontinuierlichem Abdestillie- ren des Wassers. Dann wird das Produkt kalt abge saugt und nach den Angaben des Beispiels 1 auf gearbeitet.
Der erhaltene Farbstoff ist identisch mit dem nach Beispiel 1 erhaltenen Produkt.
Process for the production of dyes The main patent relates to a process for the production of dyes which are advantageously used for dyeing plastics such as plasticized polyvinyl chloride or Polyäthy len, or paints and for the production of printing colors with very good fastness properties, which thereby is characterized in that perylene-3,4,9,10-tetracarboxylic acid or its anhydride is condensed with p-cyclohexyl-aniline.
It has now been found that a dye with similarly excellent properties is obtained if perylene-3,4,9,10-tetracarboxylic acid or its anhydride is reacted with p-isopropylaniline.
The new dye is very suitable as a pigment in the printing inks and coatings industry, for real coloring of plastics, such as plasticizer-containing polyvinyl chloride or polyethylene, also in so-called stoving enamels or for dyeing in the spinning mass.
<I> Example 1 </I> 30 parts by weight of perylene-3,4,9,10-tetracarboxylic acid dianhydride and 20 parts by volume of concentrated hydrochloric acid are added successively to 200 parts by volume of p-isopropyl aniline with stirring. The mixture is heated to 210-220 ° C. for 12 hours while the water is continuously distilled off. The product is filtered off with suction while cold, washed several times with methanol, boiled several times with dilute sodium hydroxide solution, washed neutral with hot water and dried.
The red dye, which crystallizes from quinoline in fine needles, does not melt up to 300 C, is sparingly soluble in common organic solvents and dissolves in concentrated sulfuric acid with a violet color without fluorescence. It is characterized by a striking clarity and excellent fastness properties both. in paints as well as in plastics, such as B. polyvinyl chloride mixtures, and has very good oilfastness, overspray fastness, solvent fastness, bleeding fastness and light fastness.
<I> Example 2 </I> 30 parts by weight of perylene-3,4,9,10-tetracarboxylic acid dianhydride, 23 parts by weight of p-isopropyl aniline and 15 parts by volume of concentrated hydrochloric acid are added one after the other to 210 parts by volume of quinoline . The mixture is heated to 200 to 210 ° C. for 15 hours while the water is continuously distilled off. Then the product is sucked off cold and worked up according to the information in Example 1.
The dye obtained is identical to the product obtained according to Example 1.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE351056X | 1956-03-31 | ||
| CH349727T | 1960-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH351056A true CH351056A (en) | 1960-12-31 |
Family
ID=25737062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH351056D CH351056A (en) | 1956-03-31 | 1957-03-28 | Process for the production of dyes |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH351056A (en) |
-
1957
- 1957-03-28 CH CH351056D patent/CH351056A/en unknown
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