DE1794300A1 - Anthraquinone derivatives for pigmenting high molecular weight organic products - Google Patents
Anthraquinone derivatives for pigmenting high molecular weight organic productsInfo
- Publication number
- DE1794300A1 DE1794300A1 DE19631794300 DE1794300A DE1794300A1 DE 1794300 A1 DE1794300 A1 DE 1794300A1 DE 19631794300 DE19631794300 DE 19631794300 DE 1794300 A DE1794300 A DE 1794300A DE 1794300 A1 DE1794300 A1 DE 1794300A1
- Authority
- DE
- Germany
- Prior art keywords
- molecular weight
- high molecular
- organic products
- weight organic
- anthraquinone
- 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
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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Anthrachinonderivate zum Pigmentieren von hochmolekularen organischen Erzeugnissen.Anthraquinone derivatives for pigmenting high-molecular organic Products.
Es wurde gefunden, dass sich Anthrachinonfarbstoffe der Formel hervorragend zum Pigmentieren von hochmolekularen organischen Erzeugnissen eignen.It has been found that anthraquinone dyes of the formula excellent for pigmenting high molecular weight organic products.
Die erfindungsgemäss zu verwendenden Farbstoffe erhält man, wenn man l,5-Diaminoanthrachinon mit einem 2,4-Dihalogenbenzoylhalogenid im Molverhältnis 1:2 kondensiert.The dyes to be used according to the invention receives if you l, 5-diaminoanthraquinone with a 2,4-dihalobenzoyl halide im 1: 2 molar ratio condensed.
Als Carbonsäurehalogenid verwendet man beispielsweise 2,4-Dibrombenzoyl chlorid, 2-Brom-4-chlorbenzoylchlorid, 4-Brom-2-chlorbenzoylchlorid, 2,4-Difluorbenzoylchlorid, 2-Fluor-4-benzoylchlorid, 2-Chlor-4-fluorbenzoylchlorid und insbesondere 2,4-Dichlorbenzoylchlorid Die Umsetzung erfolgt zweckmässig in einem inerten organischen Lösungsmittel, beispielsweise Nitrobenzol, Chlorbenzol oder o-Dichlorbenzol bei erhöhter Temperatur. Anstatt vom fertigen 2,4-Dihalogenbenzoylchlorid auszugehen, führt man zweckmässig die Herstellung des Säurechlorides durch Umsetzen der 2,4-Dihalogenbenzoesäure mit Thionylchlorid und die nachfolgende Kondensation des Säurechlorides mit dem Diaminoanthrachinon im gleichen Gefäss, d.h. ohne Isolierung des Säurechlorides durch. 2,4-Dibromobenzoyl, for example, is used as the carboxylic acid halide chloride, 2-bromo-4-chlorobenzoyl chloride, 4-bromo-2-chlorobenzoyl chloride, 2,4-difluorobenzoyl chloride, 2-fluoro-4-benzoyl chloride, 2-chloro-4-fluorobenzoyl chloride and especially 2,4-dichlorobenzoyl chloride The reaction is conveniently carried out in an inert organic solvent, for example Nitrobenzene, chlorobenzene or o-dichlorobenzene at an elevated temperature. Instead of the To start out finished 2,4-dihalobenzoyl chloride, one expediently carries out the preparation of the acid chloride by reacting the 2,4-dihalobenzoic acid with thionyl chloride and the subsequent condensation of the acid chloride with the diaminoanthraquinone in the same vessel, i.e. without isolating the acid chloride.
Als hochmolekulare organische Erzeugnisse seien genannt: Viscose oder Celluloseäther und -ester, beispielsweise Nitrocellulose, Acetylcellulose, Superpolyamide bzw. High molecular weight organic products are: Viscose or cellulose ethers and esters, for example nitrocellulose, acetylcellulose, Super polyamides or
Superpolyurethane oder Polyester, natürliche Harze oder Kunstharze, wie Polymerisationsharze oder Kondensationsharze, z.B. Aminoplaste, Alkydharze, Phenoplaste, Polyolfine, wie Polystyrol, Polyvinylchlorid, Polyäthylen, Polypropylen> Polyacrylnitril, Gummi, Casein, Silikon und Silikonharze.Super polyurethanes or polyesters, natural resins or synthetic resins, such as polymerization resins or condensation resins, e.g. aminoplasts, alkyd resins, Phenoplasts, polyolines, such as Polystyrene, polyvinyl chloride, polyethylene, Polypropylene> polyacrylonitrile, rubber, casein, silicone and silicone resins.
Farbstoffe ;Ausserdem lassen sich die vorteilhaft bei der Herstellung von Lacken, Farbsti£ten, kosmetischen Präparaten oder Laminierplatten verwenden. Dyes; They can also be beneficial in manufacturing on varnishes, paints, cosmetic preparations or laminating boards.
Das 1,5-Bis-(2',4'-dichoorbenzoylamino)-anthrachinin stellt zwar eine bekannte Verbindung dar (siehe deutsche Patentschrift 857 966), deren Verwendung als Pigment ist Jedoch neu und die damit erzielten hervorragenden Ergebnisse sind überraschend, Es ist nämlich bekannt, dass das 1,5-Bis-(o-chlorbenzoylamino)-anthrachinon als Pigment ungenügend migrationsecht ist (siehe schweizerische Patentschrift 402 805). Gegenüber dem in der deutschen Patentschrift 744 305 beschriebenen 1,5-Bis-(p-chlorbenzoylamino)-anthrachinon und gegenüber dem in der US-Patentschrift 2 420 453 beschriebenen isomeren 1,5-Bis-(3',4'-dichoorbenzoylamino)-anthrachinon zeigen die erfindungsgemäss zu verwendenden Farbstoffe den Vorzug einer besseren Lichtechtheit. The 1,5-bis- (2 ', 4'-dichoorbenzoylamino) -anthraquinine is indeed a known compound (see German patent specification 857 966), the use of which However, as a pigment is new and the excellent results achieved with it are Surprisingly, it is known that the 1,5-bis- (o-chlorobenzoylamino) -anthraquinone as a pigment is insufficiently resistant to migration (see Swiss patent 402 805). Compared to the 1,5-bis (p-chlorobenzoylamino) anthraquinone described in German patent specification 744 305 and to the isomeric 1,5-bis- (3 ', 4'-dichoorbenzoylamino) anthraquinone described in US Pat. No. 2,420,453 show the dyes to be used according to the invention the preference of a better one Lightfastness.
In den nachfolgenden Beispielen bedeuten die Teile, sofern nichts anderes angegeben wird, Gewichtsteile, die Prozente Gewichtsprozente, und die Temperaturen sind in Celsiusgraden angegeben. In the examples below, the parts unless they mean nothing otherwise stated, parts by weight, percentages percentages by weight, and temperatures are given in degrees Celsius.
Beispiel 1. Example 1.
65 Teile Polyvinylchlorid, 35 Teile Dioctylphthalat und 0,2 Teile 1,5-Bis-(2',4'-dichoorbenzoylamino)-anthrachinon werden miteinander verrührt und dann auf einem Zweiwalzenkalander während 7 Minuten bei 1400 eine und hergewalzt. Man erhält eine rotstichig gelb gefärbte Folie von sehr guter Licht-, Migrations-und Wetterechtheit. Selbst nach 1000-stündiger Belichtung im Fadeometer ist noch keine Farbänderung erkennbar. 65 parts of polyvinyl chloride, 35 parts of dioctyl phthalate and 0.2 part 1,5-bis- (2 ', 4'-dichoorbenzoylamino) -anthraquinone are stirred together and then rolled in on a two-roll calender for 7 minutes at 1400. A reddish-tinged yellow film with very good light, migration and light properties is obtained Weather resistance. Even after 1000 hours of exposure in the fadeometer, there is still none Color change recognizable.
Das 1,5-Bis-(2',4'-dichlorbenzolyamino)-anthrachinon ist eine bekannte Verbindung und kann durch Kondensation von l'5-Diaminoanthrachinon mit 2,4-Dichlorbenzoylchlorid im Molverhältnis 1:2 erhalten werden. 1,5-bis- (2 ', 4'-dichlorobenzolyamino) -anthraquinone is a well-known one Compound and can be obtained by condensation of l'5-diaminoanthraquinone with 2,4-dichlorobenzoyl chloride can be obtained in a molar ratio of 1: 2.
In der nachfolgenden Tabelle sind in Kolonne 1 eine Reihe weiterer
1,5-Bis- (2'4-dihalogenbenzoylamino) anthrachinone aufgeführt, die Polyvinylchlorid
in der in Kolonne 2 angegebenen Nuance färben.
Die 2-Chlor-4-fluorbenzoesäure kann erhalten werden durch Oxydation mit Kaliumpermanganat von 2-Chlor- 4- fluortoluol. Letzteres erhält man durch Umsetzen des Diazoniumchlorids von 4-Amino-2-chlortoluol mit Borfluorwasserstoffw säure und thermischer Zersetzung des gebildeten Diazoniumtetrafluoroborates. The 2-chloro-4-fluorobenzoic acid can be obtained by oxidation with potassium permanganate of 2-chloro-4-fluorotoluene. The latter is obtained by repositioning of the diazonium chloride of 4-amino-2-chlorotoluene with borofluoric acid and thermal decomposition of the diazonium tetrafluoroborate formed.
Beispiel 2. Example 2.
0,25 Teile des Farbstoffes gemäss Beispiel 1 werden mit 40 Teilen eines Alkyd-Melamin-Einbrennlackes, welcher 50% Feststoff enthält, und 4,76 Teilen Titandioxyd 24 Stunden in einer Stangenmühle gemahien. Der erhaltene Lack. wird auf eine Aluminiumfolie in dünner Schicht ausgestrichen und eine Stunde bei 1200 eingebrannt. Man erhält einen gelben Lackanstrich mit sehr guter Lichtechtheit. 0.25 parts of the dye according to Example 1 are mixed with 40 parts of an alkyd melamine stoving enamel containing 50% solids and 4.76 parts Titanium dioxide ground in a rod mill for 24 hours. The varnish obtained. will Spread a thin layer on an aluminum foil and set it for one hour at 1200 burned in. A yellow lacquer coating with very good lightfastness is obtained.
Claims (2)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1143162A CH420439A (en) | 1962-09-28 | 1962-09-28 | Process for the production of new anthraquinone dyes |
CH1061563 | 1963-08-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1794300A1 true DE1794300A1 (en) | 1971-07-08 |
Family
ID=25706991
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19631794300 Pending DE1794300A1 (en) | 1962-09-28 | 1963-09-27 | Anthraquinone derivatives for pigmenting high molecular weight organic products |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE1794300A1 (en) |
ES (1) | ES292035A1 (en) |
GB (1) | GB984110A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1129619B (en) * | 1960-12-13 | 1962-05-17 | Trilux Lenze Gmbh & Co Kg | Bracket for choke coils in lights |
DE1212633B (en) * | 1961-12-05 | 1966-03-17 | Edward Bostonian | Arrangement for screwless attachment of a ballast for fluorescent lamps |
EP0423068A1 (en) * | 1989-10-10 | 1991-04-17 | Ciba-Geigy Ag | New anthraquinone compounds |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5238984A (en) * | 1989-10-10 | 1993-08-24 | Ciba-Geigy Corporation | Dianthraquinonyl compounds |
-
1963
- 1963-09-27 ES ES292035A patent/ES292035A1/en not_active Expired
- 1963-09-27 GB GB3823863A patent/GB984110A/en not_active Expired
- 1963-09-27 DE DE19631794300 patent/DE1794300A1/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1129619B (en) * | 1960-12-13 | 1962-05-17 | Trilux Lenze Gmbh & Co Kg | Bracket for choke coils in lights |
DE1212633B (en) * | 1961-12-05 | 1966-03-17 | Edward Bostonian | Arrangement for screwless attachment of a ballast for fluorescent lamps |
EP0423068A1 (en) * | 1989-10-10 | 1991-04-17 | Ciba-Geigy Ag | New anthraquinone compounds |
Also Published As
Publication number | Publication date |
---|---|
ES292035A1 (en) | 1964-03-01 |
GB984110A (en) | 1965-02-24 |
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