DE2819570A1 - Mono:azo quinazolone pigments for plastics, lacquers etc. - with increased colour strength and insolubility - Google Patents

Mono:azo quinazolone pigments for plastics, lacquers etc. - with increased colour strength and insolubility

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Publication number
DE2819570A1
DE2819570A1 DE19782819570 DE2819570A DE2819570A1 DE 2819570 A1 DE2819570 A1 DE 2819570A1 DE 19782819570 DE19782819570 DE 19782819570 DE 2819570 A DE2819570 A DE 2819570A DE 2819570 A1 DE2819570 A1 DE 2819570A1
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DE
Germany
Prior art keywords
pigments
quinazolone
insolubility
plastics
azo
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.)
Withdrawn
Application number
DE19782819570
Other languages
German (de)
Inventor
Hartmut Dipl Chem Dr Kanter
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DE19782819570 priority Critical patent/DE2819570A1/en
Publication of DE2819570A1 publication Critical patent/DE2819570A1/en
Withdrawn legal-status Critical Current

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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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C09B29/0011—Monoazo dyes prepared by diazotising and coupling from diazotized anilines from diazotized anilines directly substituted by a heterocyclic ring (not condensed)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

New quinazolone azo pigments are of formula (II) (in which B is H or methyl; Y is Cl or Br; Z is H, Cl or Br; R1 is as Z or NO2; R2 and R3 are H or Cl; X is CN or carbamoyl). (II) have very good fastness to all solvents, and to migration, over-painting and light, giving very brilliant yellow to orange shades, some of them giving very high colour yield and strength, or unusually high covering power. Insolubility and strength are further increased above the similar pigments claimed in DT2219169.

Description

Chinazolon-AzopigmenteQuinazolone azo pigments

Zusatz zum Patent 2 219 169 und Zusatz zum Zusatzpatent (Patentanmeldung 26 55 522.6) Das Hauptpatent betrifft Farbstoffe der Formel I in der R1 Wasserstoff, Chlor, Brom oder Nitro, R2 und R3 Wasserstoff oder Chlor R4 Wasserstoff, Chlor oder Methyl und X Cyan oder Carbamoyl bedeuten.Addendum to patent 2,219,169 and addendum to additional patent (patent application 26 55 522.6) The main patent relates to dyes of the formula I in which R1 is hydrogen, chlorine, bromine or nitro, R2 and R3 are hydrogen or chlorine, R4 is hydrogen, chlorine or methyl and X is cyano or carbamoyl.

Das Zusatzpatent betrifft Farbstoffe der Formel 1> I, beidenen die Methylgruppe des Pyridinringes durch Wasserstoff ersetzt ist.The additional patent relates to dyes of the formula 1> I, both the methyl group of the pyridine ring is replaced by hydrogen.

Es wurde nun gefunden, daß Verbindungen der Formel II der B Wasserstoff oder Methyl, Y Chlor oder Brom und Z Wasserstoff, Chlor oder Brom bedeuten und Rl, R2, R3 und X die angegebenen Bedeutungen haben, ebenfalls vorziigliche Eigenschaften aufweisen.It has now been found that compounds of the formula II where B is hydrogen or methyl, Y is chlorine or bromine and Z is hydrogen, chlorine or bromine and Rl, R2, R3 and X have the meanings given, also have excellent properties.

Die neuen Farbstoffe haben Pigmentcharakter und zeichnen sich in ihren Anwendungen durch sehr gute Lösungsmittelechtheiten in allen Lösungsmitteln, Migrationsechtheit, Uberlackier- und Uberspritzechtheit und gute Lichtechtheit aus. Man erhält damit sehr brillante gelbe bis orangefarbene Färbungen.The new dyes are pigmentary and stand out in their Applications due to very good solvent fastness in all solvents, migration fastness, Fastness to overcoat and overmold and good fastness to light. One obtains with it very brilliant yellow to orange colors.

Einzelne Pigmente der Formel II sind durch außerordentlich hohe Ausgiebigkeit und Farbstärke gekennzeichnet oder sie zeigen in geeigneter physikalischer Form ein ungewöhnlich hohes Deckvermögen.Individual pigments of the formula II are extremely voluminous and color strength or they show in a suitable physical form an unusually high hiding power.

Gegenüber den Verbindungen des Hauptpatentes zeichnen sich die neuen Verbindungen durch weiter gesteigerte Unlöslichkeit und Farbstärke aus.Compared to the connections of the main patent, the new ones stand out Compounds by further increased insolubility and color strength.

Zur Herstellung der Verbindungen der Formel II kann man ein Diazoniumsalz von.Aminen der Formel III mit einer Kupplungskomponente der Formel 'umsetzen. Hinsichtlich der Verxsendung und weiterer Einzelheiten gelten die Angaben des Haupt- und Zusatzpatentes.To prepare the compounds of the formula II, a diazonium salt of amines of the formula III with a coupling component of the formula 'realize. With regard to the shipment and further details, the details of the main and additional patent apply.

In den nachfolgenden Beispielen beziehen sich Teile und Prozente auf das Gewicht. Temperaturen sind in Celsiusgraden angegeben.In the following examples, parts and percentages relate to the weight. Temperatures are given in degrees Celsius.

Beispiel 1 15>3 Teile 2-(3',5'-Dichlor-4'-aminophenyl)-chinazolon-4 werden in einer Mischung aus 250 Teilen Eisessig, 50 Teilen Propionsäure und 30 Teilen konzentrierter Salzsäure bei 500 gelöst, auf Oo gekühlt und durch Zugabe von 3,5 Teilen Natriumnitrit diazotiert. Nach einer Stunde wird überschüssiges Nitrit mit Amidosulfonsäure zerstört. Dann läßt 0 man bei 5 eine Lösung von 7,5 Teilen 2,6-Dihydroxy-3-cyan-4-methyl-pyridin in 100 Teilen Äthanol und 3 Teilen Natriumhydroxid zulaufen, rührt 2 Stunden bei Raumtemperatur, filtriert und wäscht mit Wasser. Das wasserfeuchte Rohpigment wird in 200 Teilen N-Methylpyrrolidon langsam auf 1300 erhitzt, wobei Wasser abdestilliert, 2 Stunden gerührt, heiß filtriert, mit Methanol gewaschen und getrocknet. Man erhält 21 Teile eines orangefarbenen Pulvers der Formel Auf analoge Weise erhält man die durch Angabe der Diazo- und Kupplungskomponente gekennzeichneten Pigmente: Beispiel Teile Amin Teile Teile Farbton' Kupplungs- Pigment komponente 12,60 6 CH3 16 2 i½%ir H½H orange 2 20 0 7,5 CH3 25 r BrJH2 93 cN ta NH2 HO ß OH orange Br 20 0 6,8 25 rc 1 orange 4 r CN 2 H OH Br 15,4 6,8 20 Cl 5 1 < orange- HO NH2 HO ffi H rot Cl 15>4 21 6 1, 1 NH ß CONE 21 2 NH2 HO OH orange Cl 15,47,5 22 7 jTCONa! gg orange - 17 7>5 CH3 23 cl NH2 H t gelbstichig 8 1C}2 H1H orange Beispiel Teile Amin Teile Teile Farbton Kupplungs- Pigment komponente 21,6 0 7,5 CH3 26 orange 49 NH2 H orange Br EXAMPLE 1 15> 3 parts of 2- (3 ', 5'-dichloro-4'-aminophenyl) -quinazolone-4 are dissolved in a mixture of 250 parts of glacial acetic acid, 50 parts of propionic acid and 30 parts of concentrated hydrochloric acid at 500 ° C and cooled to 0 ° and diazotized by adding 3.5 parts of sodium nitrite. After one hour, excess nitrite is destroyed with sulfamic acid. A solution of 7.5 parts of 2,6-dihydroxy-3-cyano-4-methyl-pyridine in 100 parts of ethanol and 3 parts of sodium hydroxide is then run in at 5, stirred for 2 hours at room temperature, filtered and washed with water. The water-moist crude pigment is slowly heated to 1300 in 200 parts of N-methylpyrrolidone, with water being distilled off, stirred for 2 hours, filtered hot, washed with methanol and dried. 21 parts of an orange powder of the formula are obtained The pigments identified by specifying the diazo and coupling components are obtained in an analogous manner: Example parts amine parts parts hue 'coupling pigment component 12.60 6 CH3 16 2 i½% ir H½H orange 2 20 0 7.5 CH3 25 r BrJH2 93 cN ta NH2 HO ß OH orange Br 20 0 6.8 25 rc 1 orange 4 r CN 2 H OH Br 15.4 6.8 20 Cl 5 1 <orange- HO NH2 HO ffi H red Cl 15> 4 21 6 1, 1 NH ß CONE 21 2 NH2 HO OH orange Cl 15.47.5 22 7 jTCONa! gg orange - 17 7> 5 CH3 23 cl NH2 H t yellowish 8 1C} 2 H1H orange Example parts amine parts parts hue coupling pigment component 21.6 0 7.5 CH3 26 orange 49 NH2 H orange Br

Claims (3)

Patentansprüche 1. Chinazolon-Azopigmente der allgemeinen Formel in der 5 Wasserstoff oder Methyl, R1 Wasserstoff, Chicr, Brom oder Nitro, R und R3 IJasserstoff oder Chlor, X Cyan oder Carbamoyl, Y Chlor oder Brom und Z Wasserstoff, Chlor oder Brom bedeuten.Claims 1. Quinazolone azo pigments of the general formula in which 5 is hydrogen or methyl, R1 is hydrogen, chicr, bromine or nitro, R and R3 is hydrogen or chlorine, X is cyano or carbamoyl, Y is chlorine or bromine and Z is hydrogen, chlorine or bromine. 2. Verfahren zur Herstellung von Verbindungen gemäß Anspruch 1, dadurch gekennzeichnet, daß man ein Diazoniumsalz von Aminen der Formel III mit einer Kupplungskomponente der Formel umsetzt.2. Process for the preparation of compounds according to Claim 1, characterized in that a diazonium salt of amines of the formula III with a coupling component of the formula implements. 3. Verwendung der Verbindungen gemäß Anspruch 1 als Pigmente, insbesoncere in DruckfarDen, acken oder zunststoffen.3. Use of the compounds according to claim 1 as pigments, in particular in printing inks, sticks or plastics.
DE19782819570 1978-05-05 1978-05-05 Mono:azo quinazolone pigments for plastics, lacquers etc. - with increased colour strength and insolubility Withdrawn DE2819570A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19782819570 DE2819570A1 (en) 1978-05-05 1978-05-05 Mono:azo quinazolone pigments for plastics, lacquers etc. - with increased colour strength and insolubility

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19782819570 DE2819570A1 (en) 1978-05-05 1978-05-05 Mono:azo quinazolone pigments for plastics, lacquers etc. - with increased colour strength and insolubility

Publications (1)

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DE2819570A1 true DE2819570A1 (en) 1979-11-08

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4412949A (en) * 1980-07-02 1983-11-01 Basf Aktiengesellschaft Pigments comprising cyanomethylquinazolones coupled to diazo compounds prepared from 1-aminoanthroquinones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4412949A (en) * 1980-07-02 1983-11-01 Basf Aktiengesellschaft Pigments comprising cyanomethylquinazolones coupled to diazo compounds prepared from 1-aminoanthroquinones

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