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 insolubilityInfo
- 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
- Authority
- 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- Withdrawn
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 11
- 229920003023 plastic Polymers 0.000 title claims 2
- 239000004033 plastic Substances 0.000 title claims 2
- 239000004922 lacquer Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
- 239000000460 chlorine Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- -1 chicr Substances 0.000 claims 1
- 239000000976 ink Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 3
- 230000005012 migration Effects 0.000 abstract description 2
- 238000013508 migration Methods 0.000 abstract description 2
- 238000010422 painting Methods 0.000 abstract 1
- 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
- 239000000975 dye Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- 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)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
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
Claims (3)
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)
| Publication Number | Publication Date |
|---|---|
| DE2819570A1 true DE2819570A1 (en) | 1979-11-08 |
Family
ID=6038635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782819570 Withdrawn DE2819570A1 (en) | 1978-05-05 | 1978-05-05 | Mono:azo quinazolone pigments for plastics, lacquers etc. - with increased colour strength and insolubility |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2819570A1 (en) |
Cited By (1)
| 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 |
-
1978
- 1978-05-05 DE DE19782819570 patent/DE2819570A1/en not_active Withdrawn
Cited By (1)
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |