DE1544399B - Process for the production of anthraquinonazo dyes and anthrachmonazo dyes - Google Patents
Process for the production of anthraquinonazo dyes and anthrachmonazo dyesInfo
- Publication number
- DE1544399B DE1544399B DE1544399B DE 1544399 B DE1544399 B DE 1544399B DE 1544399 B DE1544399 B DE 1544399B
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- formula
- radical
- group
- 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
- 239000000975 dye Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 anthraquinone radical Chemical class 0.000 claims description 16
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 239000000987 azo dye Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- AWACQBFBMROGQC-UHFFFAOYSA-N 1-amino-4-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2N AWACQBFBMROGQC-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KJNHYKBXQOSFJR-UHFFFAOYSA-N 2,7-diaminoanthracene-9,10-dione Chemical compound C1=C(N)C=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 KJNHYKBXQOSFJR-UHFFFAOYSA-N 0.000 description 2
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
- QIHMGEKACAOTPE-UHFFFAOYSA-N 1-amino-5-chloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2N QIHMGEKACAOTPE-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- QFNFXYPFSYJCDF-UHFFFAOYSA-N 1-hydroxy-2h-isoquinolin-3-one Chemical compound C1=CC=CC2=C(O)NC(=O)C=C21 QFNFXYPFSYJCDF-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Description
Die Erfindung betrifft ein Verfahren zur Herstellung von Anthrachinonazofarbstoffen, bei dem man Amine der FormelThe invention relates to a process for the preparation of anthraquinone azo dyes in which one amines of the formula
A -fNH2)n A -fNH 2 ) n
mit Kupplungskomponenten der Formel HK, wobei A einen Anthrachinonrest, der noch Halogenatome enthalten kann, η 1 oder 2, K einen der Restewith coupling components of the formula HK, where A is an anthraquinone radical which may also contain halogen atoms, η 1 or 2, K one of the radicals
OHOH
Die Erfindung betrifft ferner die Anthrachinonazofarbstoffe der FormelThe invention also relates to the anthraquinone azo dyes of the formula
-HC-HC
O HO H
X ein Sauerstoffatom oder die HN-Gruppe und R einen Alkylrest mit 1 bis 4 Kohlenstoffatomen, einen Aralkylrest oder einen Arylrest, der noch Substituenten enthalten kann, bedeutet, unter Bildung von Farbstoffen der FormelX is an oxygen atom or the HN group and R is an alkyl radical having 1 to 4 carbon atoms Aralkyl radical or an aryl radical which may also contain substituents means, with the formation of Dyes of the formula
= N — K)n I= N - K) n I
in der A, K und η die obengenannte Bedeutung haben, kuppelt.in which A, K and η have the meaning given above, coupling.
Amine der Formel A -(-NH2), sind z. B. folgende Verbindungen: 1 - Aminoanthrachinon, 1 - Amino-4-chloranthrachinon, 1 -Amino-S-chloranthrachinon, 2,7 - Diaminoanthrachinon oder 1,4 - Diaminoanthrachinon. Amines of the formula A - (- NH 2 ) are, for. B. the following compounds: 1 - aminoanthraquinone, 1 - amino-4-chloranthraquinone, 1-amino-S-chloranthraquinone, 2,7 - diaminoanthraquinone or 1,4 - diaminoanthraquinone.
In den Kupplungskomponenten der FormelIn the coupling components of the formula
A-fN = N — K')„A-fN = N - K ') "
in der A und η die obengenannte Bedeutung haben, K' einen der Restein which A and η have the abovementioned meaning, K 'is one of the radicals
OHOH
H, CH, C
IIII
IlIl
/C-N
C—N/ CN
C-N
Il IIl I
O HO H
steht R für einen Alkylrest mit 1 bis 4 Kohlenstoffatomen, wie einen Methyl- oder Äthylrest, für einen Aralkylrest, wie einen Benzylrest oder einen Phenyläthylrest oder für einen Arylrest, wie einen Phenyl- oder Naphthylrest, der noch Substituenten, wie Halogenatome, Nitro-, Amino-, Alkylamino-, Acylamino-, Alkoxy- oder Alkylreste mit 1 bis 4 Kohlenstoffatomen enthalten kann.R represents an alkyl radical having 1 to 4 carbon atoms, such as a methyl or ethyl radical, for one Aralkyl radical, such as a benzyl radical or a phenylethyl radical or for an aryl radical, such as a phenyl or naphthyl radical, which still has substituents such as halogen atoms, nitro, amino, alkylamino, acylamino, May contain alkoxy or alkyl radicals having 1 to 4 carbon atoms.
OHOH
OHOH
oderor
-HC-HC
/C-N/ C-N
NC—N N C-N
Il IIl I
O HO H
R'R '
X ein Sauerstoffatom oder die HN-Gruppe und R' einen Alkylrest mit 1 bis 4 Kohlenstoffatomen, einen Benzyl- oder Phenyläthylrest oder einen Phenyl-, p-Chlorphenyl-. oder Naphthylrest bedeutet.X is an oxygen atom or the HN group and R 'is an alkyl radical with 1 to 4 carbon atoms, a benzyl or phenylethyl radical or a phenyl, p-chlorophenyl-. or naphthyl radical.
Die neuen Farbstoffe sind, gegebenenfalls nach üblichen Finishmethoden, Pigmentfarbstoffe mit guten Lösungsmittelechtheiten, großer Farbstärke, klarem Farbton und hoher Lichtechtheit. Sie eignen sich für alle Zwecke der Pigmenttechnik, insbesondere für die Herstellung gefärbter Lacke oder Druckfarben. Der aus der britischen Patentschrift 925 859 bekannte, aus 1-Aminoanthrachinon und 2,4-Dihydroxychinolin erhältliche A.zofarbstoff wird durch den nach Beispiel 1 erhältlichen erfindungsgemäßen Farbstoff durch eine höhere Licht- und Wetterechtheit übertroffen. The new dyes are pigment dyes with good properties, if appropriate using customary finishing methods Solvent fastness, great color strength, clear shade and high lightfastness. You are suitable for all purposes of pigment technology, especially for the production of colored lacquers or printing inks. The one known from British patent specification 925 859, from 1-aminoanthraquinone and 2,4-dihydroxyquinoline obtainable A.zo dye is obtained by the dye according to the invention according to Example 1 surpassed by a higher light and weather fastness.
Die in den Beispielen genannten Teile und Prozente beziehen sich auf Gewichtseinheiten.The parts and percentages mentioned in the examples relate to units by weight.
22,5 Teile 1-Aminoanthrachinon werden in 250 Teilen 96%iger Schwefelsäure gelöst. Dann gießt man die Lösung auf eine Mischung aus 1000 Teilen Eiswasser und 7 Teilen Natriumnitrit, rührt 1 Stunde unter Eiskühlung nach, zerstört dann in üblicher Weise den Nitritüberschuß und saugt das Diazoniumsalz ab.22.5 parts of 1-aminoanthraquinone are in 250 parts 96% sulfuric acid dissolved. The solution is then poured onto a mixture of 1000 parts of ice water and 7 parts of sodium nitrite, stirred for 1 hour while cooling with ice, then destroyed in the usual way Dispose of the excess nitrite and sucks off the diazonium salt.
Man suspendiert das Diazoniumsalz in 1000 Teilen Wasser und gibt die Suspension anteilmäßig zu einer Lösung von 17 Teilen 1,3-Dihydroxyisochinolin, 1000 Teilen Wasser und 8 Teilen Natriumhydroxid, wobei man während der Kupplung mit verdünnter Natronlauge einen pH-Wert von 8 einhält. Es wird noch 5 Stunden nachgerührt, dann abgesaugt und mit Wasser gewaschen. Man erhält 35 Teile einesThe diazonium salt is suspended in 1000 parts of water and the suspension is proportionally added to a Solution of 17 parts of 1,3-dihydroxyisoquinoline, 1000 parts of water and 8 parts of sodium hydroxide, a pH of 8 is maintained with dilute sodium hydroxide solution during the coupling. It will Stirred for a further 5 hours, then filtered off with suction and washed with water. You get 35 parts of one
3 43 4
gelben, in organischen Lösungsmittel praktisch unlöslichen Farbstoffes der Formelyellow dye of the formula which is practically insoluble in organic solvents
O N = NO N = N
OHOH
HOHO
In analoger Weise werden unter Verwendung der in der folgenden Tabelle genannten Ausgangsstoffe die entsprechenden Farbstoffe hergestellt.In an analogous manner, using the starting materials specified in the table below the corresponding dyes produced.
DiazokomponenteDiazo component
KupplungskomponenteCoupling component
Farbecolor
1 -Aminoanthrachinon1-aminoanthraquinone
1 -Aminoanthrachinon1-aminoanthraquinone
1 -Aminoanthrachinon1-aminoanthraquinone
l-Amino-^chloranthrachinonl-amino- ^ chloroanthraquinone
1 -Amino-4-chloranthrachinon1-amino-4-chloroanthraquinone
1 -Amino-4-chloranthrachinon1-amino-4-chloroanthraquinone
OHOH
OHOH
-NH -N-NH -N
OHOH
J-NHJ-NH
N
NH2 N
NH 2
OHOH
OHOH
OHOH
RotRed
Gelbyellow
Gelbyellow
RotRed
Gelbyellow
Gelbyellow
FortsetzunsContinue us
Diazokomponente KupplungskomponenteDiazo component coupling component
Farbecolor
1 -Amino^-chloranthrachinon1-amino ^ -chloranthraquinone
1 -Amino-S-chloranthrachinon1-Amino-S-chloroanthraquinone
1 -Amino-5-chloranthrachinon1-amino-5-chloroanthraquinone
2,7-Diaminoanthrachinon (tetrazotiert)2,7-diaminoanthraquinone (tetrazotized)
1 -Aminoanthrachinon1-aminoanthraquinone
1 -Aminoanthrachinon1-aminoanthraquinone
1 -Aminoanthrachinon1-aminoanthraquinone
OHOH
-NH-NH
-N N=-N N =
-NH-NH
-NH-NH
C4H9 C 4 H 9
Gelbyellow
Gelbyellow
Gelbyellow
RotRed
RotstichiggelbReddish yellow
RotstichiggelbReddish yellow
RotstichiggelbReddish yellow
Claims (1)
HC/
HC
2. Farbstoffe der Formelin which A, K and η have the meaning given above, coupling.
2. Dyes of the formula
O H X C-N
OH
3. Der Farbstoff der FormelX denotes an oxygen atom or the HN group and R 'denotes an alkyl group with 1 to 4 carbon atoms, a benzyl or phenylethyl group or a phenyl, p-chlorophenyl or naphthyl group.
3. The dye of the formula
Family
ID=
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