DE1094897B - Process for producing a pigment - Google Patents
Process for producing a pigmentInfo
- Publication number
- DE1094897B DE1094897B DEB54251A DEB0054251A DE1094897B DE 1094897 B DE1094897 B DE 1094897B DE B54251 A DEB54251 A DE B54251A DE B0054251 A DEB0054251 A DE B0054251A DE 1094897 B DE1094897 B DE 1094897B
- Authority
- DE
- Germany
- Prior art keywords
- pigment
- dimethylaniline
- parts
- dye
- 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
- 239000000049 pigment Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 claims description 8
- 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
- 239000002253 acid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000010186 staining Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 4
- 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
- 239000000203 mixture Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 3
- -1 polyethylene Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- MZZSDCJQCLYLLL-UHFFFAOYSA-N Secalonsaeure A Natural products COC(=O)C12OC3C(CC1=C(O)CC(C)C2O)C(=CC=C3c4ccc(O)c5C(=O)C6=C(O)CC(C)C(O)C6(Oc45)C(=O)OC)O MZZSDCJQCLYLLL-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Verfahren zur Herstellung eines Pigmentfarbstoffs Aus dem Schrifttum, z. B. der deutschen Patentschrift 386 057 oder den USA.-Patentschriften 2 715127 und 2 543 747, ist es bekannt, daß man durch Umsetzung von Perylen-3,4,9,10-tetracarbonsäure und ihren Derivaten mit Ammoniak oder primären aliphatischen oder aromatischen Aminen rote bis bordorote Küpenfarbstoffe erhält, die pflanzliche Fasern, wie Baumwolle, Zellwolle oder Viscosekunstseide, aus der Küpe in roten Tönen färben.Process for the production of a pigment dye From the literature, z. B. German patent 386 057 or USA patents 2,715,127 and 2,543,747, it is known that by reacting perylene-3,4,9,10-tetracarboxylic acid and their derivatives with ammonia or primary aliphatic or aromatic amines contains red to bordeaux red vat dyes that contain vegetable fibers such as cotton, Spun rayon or viscose silk from the vat can be dyed in red tones.
Diese Farbstoffe sind jedoch in der Regel für andere Verwendungszwecke, z. B. als Pigment zum Färben von Lacken, von Weichmacher enthaltendem Polyvinylchlorid, von Polyäthylen, von Polystyrol, zum Färben in der Spinnmasse oder in Einbrennlacken, ungeeignet, da sie die hierfür erforderlichen Eigenschaften (insbesondere Lösungsmittel-, Weichmacher- und Überspritzechtheit, hohe thermische Beständigkeit, hohe Ausgiebigkeit und hohe Lichtechtheit) meist nur in unzureichendem Maß oder überhaupt nicht aufweisen. Ferner ist der Farbton dieser Farbstoffe meist sehr gedeckt und liegt zwischen Rot und Bordo.However, these dyes are usually for other uses, z. B. as a pigment for coloring paints, plasticizer-containing polyvinyl chloride, of polyethylene, of polystyrene, for dyeing in the spinning pulp or in stoving enamels, unsuitable because they have the properties required for this (especially solvent, Plasticizer and overspray fastness, high thermal resistance, high yield and high lightfastness) usually only inadequate or not at all. Furthermore, the hue of these dyes is usually very muted and lies between red and Bordo.
Es wurde nun gefunden, daß man einen hervorragend als Pigment geeigneten Farbstoff erhält, der sich zudem durch einen in dieser Verbindungsklasse ungewöhnlich klaren und leuchtenden rotorangen Farbton von hoher Lichtechtheit auszeichnet, wenn man Perylen-3,4,9, 10-tetracarbonsäure bzw. deren Säurederivate mit 2,5-Dimethylanilin kondensiert. Als Säurederivate der Perylen-3,4,9,10-tetracarbonsäure seien beispielsweise das Anhydrid und das Imid erwähnt.It has now been found that one is outstandingly suitable as a pigment A dye that is also unusual in this class of compounds clear and luminous red-orange shade of high lightfastness, if one perylene-3,4,9,10-tetracarboxylic acid or its acid derivatives with 2,5-dimethylaniline condensed. Examples of acid derivatives of perylene-3,4,9,10-tetracarboxylic acid are the anhydride and the imide mentioned.
Für die Kondensation verwendet man zweckmäßig auf je 1 Mol Perylentetracarbonsäure bzw. deren Anhydrid 25 bis 30 Mol Dimethylanilin. Ein größerer Überschuß an Dimethylanilin ist jedoch nicht schädlich. Dabei kann man in Anwesenheit oder in Abwesenheit von Lösungs- und/oder Verdünnungsmitteln, beispielsweise von Chinolin, arbeiten. Vorteilhaft verwendet man das Amin zugleich als Lösungsmittel. Die Umsetzung erfolgt zwischen 180 und 218°C, vorteilhaft zwischen 200 und 205°C, und ist in der Regel nach 7 bis 8 Stunden beendet. Zweckmäßig arbeitet man in Gegenwart von Kondensationsmitteln, z. B. von Chlorwasserstoffsäure, konzentrierter Essigsäure, Phosphorsäure oder wasserfreiem Zinkchlorid.For the condensation, it is expedient to use 1 mole of perylenetetracarboxylic acid or their anhydride 25 to 30 moles of dimethylaniline. A larger excess of dimethylaniline however, it is not harmful. You can do this in the presence or absence of Solvents and / or diluents, for example quinoline, work. Advantageous the amine is used as a solvent at the same time. The implementation takes place between 180 and 218 ° C, advantageously between 200 and 205 ° C, and is usually after 7 to Finished 8 hours. It is advisable to work in the presence of condensing agents, z. B. of hydrochloric acid, concentrated acetic acid, phosphoric acid or anhydrous Zinc chloride.
Der orangefarbene Ton und die gute Lösungsmittel-und Überspritzechtheit des neuen Pigments ist um so überraschender, als der isomere Farbstoff, der aus Perylentetracarbonsäureanhydrid und 2,6-Dimethylanilin erhältlich ist, eine schlechte Lösungsmittelechtheit aufweist. Das neue Pigment ist zum Färben von synthetischen makromolekularen Produkten, insbesondere von weichmacherhaltigen Polyvinylchlorid, von Polystyrol und für Lacke, z. B. Nitrolacke, und Druckfarben von besonderem technischem Interesse. Der nach der Erfindung erhältliche Pigmentfarbstoff ist dem aus der schweizerischen Patentschrift 101759 bekannten Farbstoff aus Perylen-3,4,9,10-tetracarbonsäure und 2,4-Dimethylanilin und dem bereits erwähnten, durch Umsetzung von Perylentetracarbonsäureanhydrid und 2,6-Dimethylanilin erhältlichen Farbstoff durch die größere Brillanz der Leinölfirnisaufstriche und der Polyvinylchlorideinfärbungen in Vollton, Weißverschnitt und Transparenz überlegen.The orange-colored shade and the good fastness to solvents and overspray of the new pigment is all the more surprising since the isomeric dye, which is obtainable from perylenetetracarboxylic anhydride and 2,6-dimethylaniline, has poor fastness to solvents. The new pigment is used for coloring synthetic macromolecular products, especially plasticized polyvinyl chloride, polystyrene and paints, e.g. B. nitro lacquers, and printing inks of particular technical interest. The pigment dye obtainable according to the invention is the dye known from Swiss patent specification 101759 of perylene-3,4,9,10-tetracarboxylic acid and 2,4-dimethylaniline and the dye already mentioned, obtainable by reacting perylenetetracarboxylic anhydride and 2,6-dimethylaniline Superior due to the greater brilliance of the linseed oil varnish spreads and the polyvinyl chloride coloring in full tone, white waste and transparency.
Die in den Beispielen angegebenen Teile und Prozentzahlen sind, soweit nicht anders angegeben, Gewichtseinheiten. Die Volumteile verhalten sich zu den Gewichtsteilen wie unter Normalbedingungen das Liter zum Kilogramm.The parts and percentages given in the examples are so far not otherwise specified, weight units. The volume parts relate to the Parts by weight like the liter to the kilogram under normal conditions.
Beispiel 1 In ein kurz auf 150 bis 155°C erhitztes Gemisch von 300 Teilen 2,5-Dimethylanilin und 43 Teilen feingemahlenem Perylen-3,4,9,10-tetracarbonsäureanhydrid trägt man 4 Teile feingepulvertes, wasserfreies Zinkchlorid ein, erhitzt die Mischung innerhalb von einer Stunde auf ungefähr 200°C, und hält darauf diese Temperatur 10 bis 12 Stunden lang ein. Danach läßt man das Umsetzungsgemisch erkalten, verdünnt es mit Methanol, saugt das abgeschiedene Umsetzungsgut ab und wäscht es mit Methanol. Das Filtergut wird nun, um nicht umgesetztes Perylentetracarbonsäureanhydrid zu entfernen, mehrfach mit 1 °/oiger wäßriger Natriumhydroxydlösung ausgekocht. Man erhält so in guter Ausbeute einen Farbstoff in Form von leuchtend orangeroten Blättchen, der in den üblichen organischen Lösungsmitteln nur wenig löslich ist und sich in konzentrierter Schwefelsäure mit violetter Farbe löst. Der Farbstoff zeichnet sich durch einen hervorragend klaren rotorangen Farbton aus und färbt Nitrolacke, Polyvinylchlorid und Polystyrol in klaren rotorangen Tönen von sehr guten Echtheitseigenschaften.Example 1 In a mixture of 300 °, heated briefly to 150 to 155 ° C Parts of 2,5-dimethylaniline and 43 parts of finely ground perylene-3,4,9,10-tetracarboxylic anhydride if 4 parts of finely powdered, anhydrous zinc chloride are introduced, the mixture is heated within one hour to about 200 ° C, and then maintains this temperature For 10 to 12 hours. The reaction mixture is then allowed to cool and diluted it with methanol, sucks off the deposited reaction material and washes it with methanol. The filter material is now to unreacted perylenetetracarboxylic anhydride remove, boiled several times with 1% aqueous sodium hydroxide solution. Man thus receives a dye in the form of bright orange-red leaflets in good yield, which is only sparingly soluble in the usual organic solvents and is in concentrated sulfuric acid with a purple color. The dye stands out with an outstandingly clear red-orange hue from and colors Nitro lacquers, polyvinyl chloride and polystyrene in clear red-orange tones of very good fastness properties.
Beispiel 2 In eine Mischung von 300 Teilen Chinolin und 15 Teilen Perylen-3,4,9,10-tetracarbonsäureanhydrid rührt man 36 Teile 2,5-Dimethylanilin ein. Sodann gibt man zu diesem Gemisch in kleinen Anteilen 10 Volumteile konzentrierte wäBrige Chlorwasserstoffsäure hinzu. Nun erhitzt man das Umsetzungsgemisch rasch auf 215 bis 220'C und hält es 12 Stunden lang bei dieser Temperatur. Dabei sorgt man dafür, daB das bei der Umsetzung entweichende Wasser aus dem Reaktionsraum entfernt wird. Nach dem Erkalten saugt man das Umsetzungsgut ab, wäscht es mit Methanol und kocht es mehrfach mit 1 °/oiger wäBriger Natriumhydroxydlösung aus. Man erhält den im Beispiel l beschriebenen Farbstoff in guter Ausbeute.Example 2 36 parts of 2,5-dimethylaniline are stirred into a mixture of 300 parts of quinoline and 15 parts of perylene-3,4,9,10-tetracarboxylic anhydride. 10 parts by volume of concentrated aqueous hydrochloric acid are then added to this mixture in small portions. The reaction mixture is now heated rapidly to 215 to 220 ° C. and kept at this temperature for 12 hours. Care is taken to ensure that the water which escapes during the reaction is removed from the reaction space. After cooling, the reaction material is filtered off with suction, washed with methanol and boiled several times with 1% aqueous sodium hydroxide solution. The dye described in Example 1 is obtained in good yield.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB54251A DE1094897B (en) | 1959-07-31 | 1959-07-31 | Process for producing a pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB54251A DE1094897B (en) | 1959-07-31 | 1959-07-31 | Process for producing a pigment |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1094897B true DE1094897B (en) | 1960-12-15 |
Family
ID=6970540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB54251A Pending DE1094897B (en) | 1959-07-31 | 1959-07-31 | Process for producing a pigment |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1094897B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1230946B (en) * | 1962-11-09 | 1966-12-22 | Basf Ag | Process for the preparation of dyes of the perylenetetracarboximide series |
| FR2327288A1 (en) * | 1975-10-11 | 1977-05-06 | Basf Ag | PIGMENTARY DIIMIDES OF PERYLENE-3,4,9,10-TETRACARBOXYLIC ACID, THEIR PREPARATION AND USES |
| EP0042819A1 (en) * | 1980-06-23 | 1981-12-30 | Ciba-Geigy Ag | Process for the preparation of opaque perylene-tetracarboxylic-bis-(3,5-dimethylphenyl imide) |
| US4446324A (en) * | 1980-12-27 | 1984-05-01 | Basf Aktiengesellschaft | Perylenetetracarboxylic acid diimides and their use |
| US4742170A (en) * | 1984-10-03 | 1988-05-03 | Hoechst Aktiengesellschaft | Mix-crystal pigments based on perylenetetracarbimides, process for their preparation, and their use |
| US4769460A (en) * | 1984-10-03 | 1988-09-06 | Hoechst Aktiengesellschaft | Mix-crystal pigments based on perylenetetracarbimides, process for preparing 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH101759A (en) * | 1923-01-03 | 1923-10-16 | Kalle & Co Ag | Process for the preparation of a vat dye. |
-
1959
- 1959-07-31 DE DEB54251A patent/DE1094897B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH101759A (en) * | 1923-01-03 | 1923-10-16 | Kalle & Co Ag | Process for the preparation of a vat dye. |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1230946B (en) * | 1962-11-09 | 1966-12-22 | Basf Ag | Process for the preparation of dyes of the perylenetetracarboximide series |
| FR2327288A1 (en) * | 1975-10-11 | 1977-05-06 | Basf Ag | PIGMENTARY DIIMIDES OF PERYLENE-3,4,9,10-TETRACARBOXYLIC ACID, THEIR PREPARATION AND USES |
| EP0042819A1 (en) * | 1980-06-23 | 1981-12-30 | Ciba-Geigy Ag | Process for the preparation of opaque perylene-tetracarboxylic-bis-(3,5-dimethylphenyl imide) |
| US4404386A (en) * | 1980-06-23 | 1983-09-13 | Ciba-Geigy Corporation | Process for the preparation of opaque perylenetetracarboxylic acid bis-(3,5-dimethylphenylimide) |
| US4446324A (en) * | 1980-12-27 | 1984-05-01 | Basf Aktiengesellschaft | Perylenetetracarboxylic acid diimides and their use |
| US4742170A (en) * | 1984-10-03 | 1988-05-03 | Hoechst Aktiengesellschaft | Mix-crystal pigments based on perylenetetracarbimides, process for their preparation, and their use |
| US4769460A (en) * | 1984-10-03 | 1988-09-06 | Hoechst Aktiengesellschaft | Mix-crystal pigments based on perylenetetracarbimides, process for preparing 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 |
| US5154770A (en) * | 1984-10-03 | 1992-10-13 | Hoechst Aktiengesellschaft | Mix-crystal pigments based on perylenetetracarbimides, process for their preparation and their use |
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