DE1544394A1 - Water-insoluble azo dyes - Google Patents
Water-insoluble azo dyesInfo
- Publication number
- DE1544394A1 DE1544394A1 DE19661544394 DE1544394A DE1544394A1 DE 1544394 A1 DE1544394 A1 DE 1544394A1 DE 19661544394 DE19661544394 DE 19661544394 DE 1544394 A DE1544394 A DE 1544394A DE 1544394 A1 DE1544394 A1 DE 1544394A1
- Authority
- DE
- Germany
- Prior art keywords
- water
- parts
- group
- formula
- dyes
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B31/00—Diffusion or doping processes for single crystals or homogeneous polycrystalline material with defined structure; Apparatus therefor
- C30B31/06—Diffusion or doping processes for single crystals or homogeneous polycrystalline material with defined structure; Apparatus therefor by contacting with diffusion material in the gaseous state
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
Wasserunlösliche AzofarbstoffeWater-insoluble azo dyes
Diese Erfiidun- uetrifft ueue wasserunlösliche Azofarbstoffe der all/je-.ieiueii Formel .This invention applies to new water-insoluble azo dyes of the all / je-.ieiueii formula.
HO-OHO-O
N=IJ-KN = IJ-K
In- der Z uen liest -N=C(OIl)- .bzw.. -NH-CO- oder -IiII-, A zusarn- :,;eii riit der Gruppe -C=C- des heterocyclischen Rinkes einen aus ein ois drei ilinien bestehenden Rest, der noch substituiert sein kann/von wasserlöallohinaehenden Gruppen jedoch frei lot, K einen der ilesteUEN domestic the Z reads -N = C (Oil) - .bzw .. -NH-CO- or -IiII-, A zusarn-:; With the group -C = C- of the heterocyclic ring, a radical consisting of one or three lines, which can still be substituted / but free of water-soluble groups, K is one of the radicals
undand
C-HC-H
I A HO IA HO
und li ein■-Wasserstoffatom,, eine Hydroxy-, Amino- oder Meroaptogruppe oder einen Arylrest bedeuten.and li is a hydrogen atom, a hydroxy, amino or meroapto group or mean an aryl radical.
4/6.64 / 6.6
/2/ 2
109810/1701109810/1701
BADBATH
P 15 44P 15 44
-2--2-
O. Z. 24 092O. Z. 24 092
Die neuen Farbstoffe werden in an sich bekannter V/eise durch Kondensation oder Azokupplung erhalten, vorzugsweise durch Kupplung der Diazoverbindungen von Aminen der FormelThe new dyes are obtained in a manner known per se by condensation or azo coupling, preferably by Coupling of the diazo compounds of amines of the formula
-OH-OH
IIII
mit Kupplungskomponenten der Formel HK, wobei A, Z und K die obengenannte Bedeutung haben.with coupling components of the formula HK, where A, Z and K have the abovementioned meanings.
Der Rest A im Molekülteil der Diazokomponenten bildet aus am -The radical A in the molecular part of the diazo components forms from am -
t tt t
men mit der Gruppe -C=C- des heterocyclischen Ringes z.B. einen Benzol-, Naphthalin-, Anthraoen- oder Anthrachinonrest, bevorzugt jedoch Φη Benzolrest. Die Reste A können noch Substituenten, ausgenommen jedoch wasserlöslichmachende Gruppen, enthalten, z.B. Halogenatome, Alkylreste mit 1 bis 5 Kohlenstoffatomen Alkoxygruppen, wie Methoxygruppen, Nitrogruppen, Arylgruppen oder Aryloxygruppen.men with the group -C = C- of the heterocyclic ring e.g. a benzene, naphthalene, anthraquinone or anthraquinone residue, however, Φη benzene radical is preferred. The radicals A can also have substituents but with the exception of water-solubilizing groups, e.g. halogen atoms, alkyl radicals with 1 to 5 carbon atoms Alkoxy groups, such as methoxy groups, nitro groups, Aryl groups or aryloxy groups.
Amine der Formel II sind z.B. die VerbindungenAmines of Formula II are, for example, the compounds
OH, H1 OH, H 1
undand
1098107170110981071701
ρ 15 44 594.4 —3- ■ O.Z. 24 092ρ 15 44 594.4 -3- ■ O.Z. 24 092
Diese Amine sind aus den heterocyclischen Grundkörpern z.B. durch Nitrierung und Reduktion der Nitrogruppen erhältlich.These amines are derived from the heterocyclic basic structures e.g. obtainable by nitration and reduction of the nitro groups.
Als Kupplungskomponenten der Formel HK kommen die VerbindungenThe compounds are used as coupling components of the formula HK
OH1 OHOH 1 OH
oder Verbindungen der allgemeinen Formelor compounds of the general formula
II .-■■■■ - - - -II .- ■■■■ - - - -
0HH 0H H
in Betracht. Dabei ist R ein Wasserstoffatom, eine Hydroxy-, Amino- oder Mercaptogruppe oder ein Arylrest, wie ein Phenylrest, der noch Substituenten, wie Halogenätome, Nitro-, Amino-, Alkylamino-, Acylamino- oder Alkylreste mit 1 bis 5 Kohlenstoffatomen tragen kann, wobei die Alkylreste noch Alkoxy-, Aryloxy- oder Hydroxylgruppen enthalten können.into consideration. R is a hydrogen atom, a hydroxy, Amino or mercapto group or an aryl radical, such as a phenyl radical, which still have substituents such as halogen atoms, nitro, amino, alkylamino, acylamino or alkyl radicals with 1 to 5 carbon atoms can carry, it being possible for the alkyl radicals to contain alkoxy, aryloxy or hydroxyl groups.
Die erfindungsgemäß erhältlichen Farbstoffe eignsn sich vorzüglich als Pigmentfarbstoffe. Sie zeichnen sich aus durch eine gute Lösungsmittelechtheit, hohe Farbstärke, klaren Färb-The dyes obtainable according to the invention are eminently suitable as pigment dyes. They are characterized by good solvent fastness, high color strength, clear color
109810/1701109810/1701
ton und eine gute Lientechtheit. Man kann sie für alle Zwecke der Pigmenttechnik verwenden, insbesondere fi"1 die Herstellung gefärbter Lacke oder Druckfarben.tone and good light fastness. They can be used for all purposes of the pigment technology, particularly fi "1, the production of colored paints or inks.
Die in den Beispielen angegebenen Teile sind Gewichtsteile.The parts given in the examples are parts by weight.
17,7 Teile 6-Amino-2,3-dihydro:xychinoxalin werden in 200 Teilen Wasser und 25 Teilen conz. Salzsäure mit 6,9 Teilen Natriumnitrit wie üblich diazotiert. Die Suspension des schwerlöslichen Diazoniumsalzes wird auf eine Lösung gegeben., die' aus 16,5 Teilen 1,5-Dihydroxyisochinolin, 16 Teilen 50'$iger Natronlauge, I5 Teilen Natriumacetat und 500 Teilen Wasser besteht. Nach Rühren über Nacht wird der Rückstand abgesaugt, gewaschen und getrocknet. Man erhält 33 Teile des Farbstoffs der Formel17.7 parts of 6-amino-2,3-dihydro: xychinoxalin are concentrated in 200 parts of water and 25 parts. Hydrochloric acid is diazotized as usual with 6.9 parts of sodium nitrite. The suspension of the sparingly soluble diazonium salt is poured into a solution consisting of 16.5 parts of 1,5-dihydroxyisoquinoline, 16 parts of 50% sodium hydroxide solution, 15 parts of sodium acetate and 500 parts of water. After stirring overnight, the residue is filtered off with suction, washed and dried. 33 parts of the dye of the formula are obtained
als orgBgerotes Pulver.as an organic red powder.
Verwendet man entsprechende Teile der in der folgenden Tabelle angegebenen Diazo- und Kupplungskomponenten,, so erhält man auf analoge V/eise ähnliche Farbstoffe mit den in der Tabelle angegebenen Farbtönen.If corresponding parts of the diazo and coupling components given in the table below are used, this is obtained analogous dyes with the color shades given in the table are used.
109810/1701 BAB ORIGINAL /5109810/1701 BAB ORIGINAL / 5
HOHO
HOHO
SIISII
■or-ange■ or-ange
HO, HO'HO, HO '
HOHO
NH2 NH 2
NH.NH.
IIII
ΓηΓη
HOHO
HOHO
gelbyellow
gelbyellow
gelbyellow
/6/ 6
1098107170110981071701
-6--6-
Beispiel AminExample amine
Kuppl.
KomponenteClutch
component
Farbecolour
H2:H 2 :
OHOH
OHOH
OHOH
orangeorange
■ ■ «a»■ ■ «a»
Λ γ"Η γ,, Λ γ "Η γ ,,
γΝ Viγ Ν Vi
0Η HO 0Η HO
iHiH
HO OHO O
H,H,
OH HOOHH O
orangeorange
gelbyellow
H2NH 2 N
■Na■ Well
OHOH
K gelbK yellow
OH H0' HOH H0 'H
/7/ 7
109810/1701109810/1701
-7-Ο.Ζ. 24 -7- Ο.Ζ. 24
Beispiel AminExample amine
Kuppl.
KomponenteClutch
component
Farbecolour
OHOH
OHOH
orageorage
|[ V OH| [V OH
OHOH
gelbyellow
1414th
>-0H> -0H
HOHO
N H orangeN H orange
H2NH 2 N
HOHO
1616
HO gelbHO yellow
/8/8th
1098 10/17011098 10/1701
15U39415U394
O.ζ. 24 092O.ζ. 24 092
Beispiel Amin Kuppl.
KomponenteExample amine coupling.
component
Farbecolour
17 H,17 H,
HOHO
gelbyellow
18 H,18 H,
OHOH
OHOH
HO gelbHO yellow
109810/1701109810/1701
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0085642 | 1966-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1544394A1 true DE1544394A1 (en) | 1971-03-04 |
Family
ID=6983010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661544394 Pending DE1544394A1 (en) | 1966-02-03 | 1966-02-03 | Water-insoluble azo dyes |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH469062A (en) |
| DE (1) | DE1544394A1 (en) |
| FR (1) | FR1510398A (en) |
| GB (1) | GB1136673A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0761764A1 (en) * | 1995-08-09 | 1997-03-12 | Hoechst Aktiengesellschaft | Water-insoluble azo colouring agents derived from aminoquinazolinediones |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4028322A (en) * | 1972-07-13 | 1977-06-07 | Ciba-Geigy Corporation | 6-Methylbenzimidazolonylazobarbituric acid pigment |
| US4171301A (en) * | 1972-07-13 | 1979-10-16 | Ciba-Geigy Corporation | Monoazo pigments containing barbituric acid derivatives |
| CH566371A5 (en) * | 1972-07-13 | 1975-09-15 | Ciba Geigy Ag | |
| DE2533529A1 (en) * | 1975-07-26 | 1977-02-10 | Basf Ag | AZOPIGMENTS |
-
1966
- 1966-02-03 DE DE19661544394 patent/DE1544394A1/en active Pending
-
1967
- 1967-01-11 CH CH34367A patent/CH469062A/en unknown
- 1967-02-02 GB GB510167A patent/GB1136673A/en not_active Expired
- 1967-02-03 FR FR93657A patent/FR1510398A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0761764A1 (en) * | 1995-08-09 | 1997-03-12 | Hoechst Aktiengesellschaft | Water-insoluble azo colouring agents derived from aminoquinazolinediones |
| US5747566A (en) * | 1995-08-09 | 1998-05-05 | Hoechst Aktiengesellschaft | Water-insoluble azo colorants based on aminoquinazolinediones |
Also Published As
| Publication number | Publication date |
|---|---|
| CH469062A (en) | 1969-02-28 |
| FR1510398A (en) | 1968-01-19 |
| GB1136673A (en) | 1968-12-11 |
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