CH637672A5 - Azo. - Google Patents
Azo. Download PDFInfo
- Publication number
- CH637672A5 CH637672A5 CH94379A CH94379A CH637672A5 CH 637672 A5 CH637672 A5 CH 637672A5 CH 94379 A CH94379 A CH 94379A CH 94379 A CH94379 A CH 94379A CH 637672 A5 CH637672 A5 CH 637672A5
- Authority
- CH
- Switzerland
- Prior art keywords
- yellow
- hydrogen
- parts
- formula
- optionally substituted
- Prior art date
Links
- 239000001257 hydrogen Substances 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 20
- 239000000975 dye Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- -1 nitro, methyl Chemical group 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000460 chlorine Chemical group 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000003609 aryl vinyl group Chemical group 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 150000003459 sulfonic acid esters Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- 229910006074 SO2NH2 Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 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
- C09B29/0003—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)
-
- 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)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Pyridine Compounds (AREA)
Description
637 672 637 672
2 2nd
PATENTANSPRÜCHE 1. Azofarbstoffe der allgemeinen Formel z I, PATENT CLAIMS 1. Azo dyes of the general formula z I,
0 0
III III
io kuppelt. io couples.
Die Erfindung betrifft Verbindungen der allgemeinen 15 Formel I The invention relates to compounds of general formula I
in der in the
X Wasserstoff, Chlor, Brom, Nitro, Methyl, Äthyl, Methoxy, Äthoxy, Trifluormethyl, Sulfonsäureester oder gegebenenfalls substituiertes Sulfamoyl, X is hydrogen, chlorine, bromine, nitro, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, sulfonic acid ester or optionally substituted sulfamoyl,
Y Wasserstoff, Chlor oder Brom, Y is hydrogen, chlorine or bromine,
Z Wasserstoff, Acetyl, Cyan oder gegebenenfalls substituiertes Carbamoyl, Z is hydrogen, acetyl, cyan or optionally substituted carbamoyl,
R1 Wasserstoff, sauerstoffhaltiges und gegebenenfalls durch Aryl substituiertes Ci- bis Cio-Alkyl, Phenyl-Ci- bis Cs-alkyl, Arylvinyl oder einen Rest der Formel (CH2)mCOOR4, R2 Wasserstoff, Ci- bis C3-Alkyl, Hydroxy oder Amino, R3 Wasserstoff, gegebenenfalls durch Ci- bis C4-Alkoxy oder Phenyl-substituiertes Ci- bis Cs-Alkyl m die Zahlen 0 bis 5 und R1 hydrogen, oxygen-containing and optionally substituted by aryl Ci to Cio alkyl, phenyl Ci to Cs alkyl, aryl vinyl or a radical of the formula (CH2) mCOOR4, R2 hydrogen, Ci to C3 alkyl, hydroxy or amino, R3 is hydrogen, optionally substituted by Ci to C4 alkoxy or phenyl-substituted Ci to Cs alkyl, m the numbers 0 to 5 and
R4 Wasserstoff, gegebenenfalls substituiertes Ci- bis C8-Alkyl, Aralkyl, Cycloalkyl öder Aryl bedeuten. 2. Farbstoffe gemäss Anspruch 1 der Formel Ia R4 is hydrogen, optionally substituted C 1 -C 8 -alkyl, aralkyl, cycloalkyl or aryl. 2. Dyes according to claim 1 of formula Ia
0-N 0-N
Ia, Yes,
25 25th
I, I,
H' H'
R3 R3
in der in the
X1 Wasserstoff, Trifluormethyl, Chlor oder Brom, B1 Alkoxyalkyl mit bis zu 10 C-Atomen, Aryloxyalkyl mit bis zu 10 C-Atomen oder Arylvinyl mit 8 bis 10 C-Atomen und B2 Wasserstoff, Methyl oder Äthyl bedeuten. X1 is hydrogen, trifluoromethyl, chlorine or bromine, B1 is alkoxyalkyl having up to 10 C atoms, aryloxyalkyl having up to 10 C atoms or arylvinyl having 8 to 10 C atoms and B2 is hydrogen, methyl or ethyl.
3. Verfahren zur Herstellung von Farbstoffen gemäss Anspruch 1, dadurch gekennzeichnet, dass man eine Diazo-verbindung von Aminen der Formel II 3. A process for the preparation of dyes according to claim 1, characterized in that a diazo compound of amines of the formula II
in der in the
30 X Wasserstoff, Chlor, Brom, Nitro, Methyl, Äthyl, Methoxy, Äthoxy, Trifluormethyl, Sulfonsäureester oder gegebenenfalls substituiertes Sulfamoyl, 30 X hydrogen, chlorine, bromine, nitro, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, sulfonic acid ester or optionally substituted sulfamoyl,
Y Wasserstoff, Chlor oder Brom, Y is hydrogen, chlorine or bromine,
Z Wasserstoff, Acetyl, Cyan oder gegebenenfalls substitu-35 iertes Carbamoyl, Z is hydrogen, acetyl, cyan or optionally substituted carbamoyl,
R1 Wasserstoff, sauerstoffhaltiges und gegebenenfalls durch Aryl substituiertes Ci- bis Cio-Alkyl, Phenyl-Ci- bis C4-alkyl, Arylvinyl oder einen Rest der Formel (CH2)mCOOR4, R2 Wasserstoff, Ci- bis C3-Alkyl, Hydroxy oder Amino, 40 R3 Wasserstoff, gegebenenfalls durch Ci- bis C4-Alkoxy oder Phenyl substituiertes Ci - bis Cs-Alkyl, R1 hydrogen, oxygen-containing and optionally substituted by aryl Ci to Cio alkyl, phenyl Ci to C4 alkyl, aryl vinyl or a radical of the formula (CH2) mCOOR4, R2 hydrogen, Ci to C3 alkyl, hydroxy or amino, 40 R3 hydrogen, optionally substituted by Ci to C4 alkoxy or phenyl Ci to Cs alkyl,
m die Zahlen 0 bis 5 und m the numbers 0 to 5 and
R4 Wasserstoff, gegebenenfalls substituiertes Ci- bis Cs-Alkyl, Aralkyl, Cycloalkyl oder Aryl bedeuten. 45 Sulfonsäureester- und Sulfamoylgruppen für X sind beispielsweise: R4 is hydrogen, optionally substituted Ci to Cs alkyl, aralkyl, cycloalkyl or aryl. 45 sulfonic ester and sulfamoyl groups for X are, for example:
SGhOCéHs, SO2OC6H4CH3, SO2OC6H4CÌ, SOzOCs&CCftiX SO2OC6H4OCH3, SO2NH2, SO2NHCH3, SO2NHC2H5, SGhOCéHs, SO2OC6H4CH3, SO2OC6H4CÌ, SOzOCs & CCftiX SO2OC6H4OCH3, SO2NH2, SO2NHCH3, SO2NHC2H5,
50 50
SO2NHC3H7, SO2NHC4H9, SO2NHCH2CH SO2NHC3H7, SO2NHC4H9, SO2NHCH2CH
2H5 c4H9' 2H5 c4H9 '
55 S02N(CH3)2, S02N(C2H5)2, S02N(C3H7)2, S02N(C4HS)2, S02NHC6H5, S02NHC6H4C1, S02NHC6H4CH3, S02NHC6H40CH3, 55 S02N (CH3) 2, S02N (C2H5) 2, S02N (C3H7) 2, S02N (C4HS) 2, S02NHC6H5, S02NHC6H4C1, S02NHC6H4CH3, S02NHC6H40CH3,
SOoN SOoN
60 d. 60 d.
II II
O ' S02V) ' O 'S02V)'
PA N 0 PA N 0
" 2 V_/ "2 V_ /
oder SOgNH— or SOgNH—
65 65
mit einer Verbindung der Formel III with a compound of formula III
Carbamoylreste Z sind z.B. neben CONH2: CONHCH3, CONHC2H5, CONHC3H7, CONHC4H9, CONHC2H4OCH3 oder CON(CH3)2. Carbamoyl Z are e.g. next to CONH2: CONHCH3, CONHC2H5, CONHC3H7, CONHC4H9, CONHC2H4OCH3 or CON (CH3) 2.
3 3rd
637672 637672
Reste R1 und R4 sind neben Wasserstoff beispielsweise: In addition to hydrogen, residues R1 and R4 are, for example:
(CH2)nOCH3, (CH2)nOC2H5, (CI^nOCaHv, (CH2)nOC4H9, (CH2)nOC6Hi3, (CH2)nOCsHi7, (CH2)nOC8Hi7, (CH2) nOCH3, (CH2) nOC2H5, (CI ^ nOCaHv, (CH2) nOC4H9, (CH2) nOC6Hi3, (CH2) nOCsHi7, (CH2) nOC8Hi7,
R R
(CH2)nOCH2CH: (CH2) nOCH2CH:
^H, ^ H,
ÒC ÒC
III III
-C4H9 -C4H9
HO HO
N N
' 3 R '3 rows
(CH2)nOC6Hu, (CH2)nOC6H5, (CH2)nOC6H4CH3, (CH2)„0C6H4C1, (CH2)nOC6H3(CH3)2, (CH2)nOCH2C6H>, (CH2)nOCH2C6H4CH3,(CH2)nOC2H4C6H5, (CH2)n0C2H40C6H5, (CH2)„0C2H40C6H4CH3, (CH2)n0C2H40C6H4Cl, (CH2)n0C2H40C6H3(CH3)2, CH2C6H5, C2H4C6H5, (CH2) nOC6Hu, (CH2) nOC6H5, (CH2) nOC6H4CH3, (CH2) „0C6H4C1, (CH2) nOC6H3 (CH3) 2, (CH2) nOCH2C6H>, (CH2) nOCH2C6H4CH3, (CH2) nOC0H4C5H4C , (CH2) "0C2H40C6H4CH3, (CH2) n0C2H40C6H4Cl, (CH2) n0C2H40C6H3 (CH3) 2, CH2C6H5, C2H4C6H5,
CHz-CH-CeHs, .CHOCH2QH5, CHz-CH-CeHs, .CHOCH2QH5,
I I I I
CH3 CH3 CH3 CH3
CH2-0-CH2CH< CH2-0-CH2CH <
X4H9 X4H9
-C2H5 -C2H5
10 in an sich bekannter Weise umsetzen. Einzelheiten der Reaktionen können den Beispielen entnommen werden, in denen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht beziehen. 10 implement in a conventional manner. Details of the reactions can be found in the examples, in which parts and percentages, unless stated otherwise, relate to the weight.
Die Verbindungen der Formel I eignen sich zum Färben 15 und Bedrucken von synthetischen Fasern, insbesondere Poly-estern. Man erhält vorwiegend gelbe Färbungen mit ausgezeichneten Echtheiten, von denen die Licht- und thermischen Echtheiten hervorzuheben sind. Ferner ist die hohe Farbstärke einiger Verbindungen zu erwähnen. 20 Von besonderer Bedeutung sind Verbindungen der Formel Ia The compounds of formula I are suitable for dyeing and printing synthetic fibers, in particular polyesters. Mainly yellow dyeings are obtained with excellent fastness properties, of which the light and thermal fastness properties are to be emphasized. The high color strength of some compounds should also be mentioned. Compounds of the formula Ia are of particular importance
-CH=CH-C6Hs, -CH=CH-C6H4CH3, -CH=CH-C6H4C1, -CH=CH-CeH40CH3 oder -CH = CH-C6Hs, -CH = CH-C6H4CH3, -CH = CH-C6H4C1, -CH = CH-CeH40CH3 or
-CH=C<^ , n ist dabei 1 oder 2? -CH = C <^, where n is 1 or 2?
^CeHs ^ CeHs
Für R4 sind darüber hinaus zusammen: CHj, ans, C3H7, C4H9, CsHn, CeHn, C7H15, CsHn, For R4 are also together: CHj, ans, C3H7, C4H9, CsHn, CeHn, C7H15, CsHn,
25 25th
I a, I a,
CH2CH< CH2CH <
-C2H5 -C2H5
-C4H9 -C4H9
(CH2)„C6H5, CôHs oder C6H4CH3. (CH2) "C6H5, CôHs or C6H4CH3.
Reste R3 sind neben Wasserstoff z.B.: In addition to hydrogen, residues R3 include:
CH3, C2H5, C3H7, C4H9, CöHi3, CsHn, CH3, C2H5, C3H7, C4H9, CöHi3, CsHn,
CH2CH<" CH2CH2OCH3, CH2CH <"CH2CH2OCH3,
\C4H9 \ C4H9
' 2 '2
Bd Vol
35 in der 35 in
X1 Wasserstoff, Trifluormethyl, Chlor oder Brom, B1 Alkoxyalkyl mit bis zu 10 C-Atomen, Aryloxyalkyl mit bis zu 10 C-Atomen oder Arylvinyl mit 8 bis 10 C-Atomen und B2 Wasserstoff, Methyl oder Äthyl bedeuten. X1 is hydrogen, trifluoromethyl, chlorine or bromine, B1 is alkoxyalkyl having up to 10 C atoms, aryloxyalkyl having up to 10 C atoms or arylvinyl having 8 to 10 C atoms and B2 is hydrogen, methyl or ethyl.
40 Bevorzugte Reste B1 sind z.B.: 40 Preferred residues B1 include:
CH2CH2OCH3, CH2CH2OC2H5, CH2CH2OC3H7, CH2CH2OC4H9, CH2CH20C6Hl3, CH2CH2OC8H17, CH2CH2OCH3, CH2CH2OC2H5, CH2CH2OC3H7, CH2CH2OC4H9, CH2CH20C6Hl3, CH2CH2OC8H17,
45 45
CH2CH2OCH2C» CH2CH2OCH2C »
2H5 C4H9' 2H5 C4H9 '
CH2CH2OCH2C6H5, CH2CH2OCH2CH2C6H5, so CH2CH2OCH2C6H4CH3 oder CH2OCH2C6H5. CH2CH2OCH2C6H5, CH2CH2OCH2CH2C6H5, so CH2CH2OCH2C6H4CH3 or CH2OCH2C6H5.
CH2CH2OC2HS, CH2CH2OC4H9, (CH2)3OCH3, (CH2)3OC2H5, CH2C6H5 oder CH2CH2C6H5. CH2CH2OC2HS, CH2CH2OC4H9, (CH2) 3OCH3, (CH2) 3OC2H5, CH2C6H5 or CH2CH2C6H5.
Zur Herstellung der Verbindungen der Formel I kann man eine Diazoverbindung von Aminen der Formel II To prepare the compounds of the formula I, a diazo compound of amines of the formula II
0 — N N 0 - N N
jL R1 jL R1
NH, NH,
mit einer Verbindung der Formel III with a compound of formula III
II II
Für B2 ist Methyl besonders bevorzugt. Methyl is particularly preferred for B2.
Die zu den Beispielen gehörenden Formeln sind auf den Zeichenblättern zusammengestellt. Beispiel- und Formel-55 nummern stimmen dabei überein. The formulas belonging to the examples are shown on the drawing sheets. Example and formula 55 numbers match.
Beispiel 1 example 1
11,8 Teile der Verbindung der Formel siehe Zeichenblatt Nr. 1, Beispiel 1 a werden unter Erwärmen in 110 Teilen so Eisessig gelöst. Dazu gibt man nach Abkühlen auf Raumtemperatur 12 Raumteile einer 33%igen wässrigen Salzsäurelösung und danach kühlt man durch Zusetzen von Eise auf 0 bis 5°C ab. Nach Versetzen mit 14 Raumteilen einer 23%igen wässrigen Natriumnitritlösung wird 2 Stunden bei 0 bis 5°C «s gerührt und nach beendeter Diazotierung überschüssige salpetrige Säure mit Amidosulfonsäure zerstört. Nun wird der pH-Wert der Diazoniumsalzlösung mit Natriumacetat auf 4,1 bis 4,3 gestellt, danach lässt man eine Lösung von 6,5 11.8 parts of the compound of the formula see drawing sheet No. 1, Example 1 a are dissolved with heating in 110 parts of glacial acetic acid. After cooling to room temperature, 12 parts of a 33% aqueous hydrochloric acid solution are added and then the mixture is cooled to 0 to 5 ° C. by adding ice. After 14 parts of a 23% aqueous sodium nitrite solution have been added, the mixture is stirred at 0 to 5 ° C. for 2 hours and, after the diazotization has ended, excess nitrous acid is destroyed with amidosulfonic acid. Now the pH of the diazonium salt solution is adjusted to 4.1 to 4.3 with sodium acetate, after which a solution of 6.5 is left
637 672 637 672
Teilen l,4-Dimethyl-2-hydroxy-3-cyan-pyridon-6 in einem Gemisch aus 300 Raumteilen Wasser, 4 Teilen 50%iger Natronlauge und 100 Teilen Eis zulaufen. Die Kupplung wird mit Natronlauge auf einen pH-Wert von 4,5 eingestellt und ist dann rasch beendet. Parts of 1,4-dimethyl-2-hydroxy-3-cyanopyridone-6 run in a mixture of 300 parts by volume of water, 4 parts of 50% sodium hydroxide solution and 100 parts of ice. The coupling is adjusted to a pH of 4.5 with sodium hydroxide solution and is then quickly ended.
Man heizt das Farbstoffgemisch auf 70°C auf, saugt ausgefallenen Farbstoff ab, wäscht mit Wasser und trocknet. Man_ erhält 18 Teile eines gelben Pulvers der Formel siehe Zeichenblatt Nr. 1, Beispiel 1 b. The dye mixture is heated to 70 ° C., the precipitated dye is filtered off with suction, washed with water and dried. You get 18 parts of a yellow powder of the formula see drawing sheet No. 1, example 1 b.
Der sehr ergiebige Farbstoff zieht aussergewöhnlich sub-stantiv (vollständige Baderschöpfung) auf Polyäthylente-rephthalatgewebe nach HT- und Druck-Färbeverfahren auf. Man erhält licht- und thermofixierechte gelbe Färbungen. The very productive dye draws exceptionally sub-stantive (complete bath exhaustion) on polyethylene terephthalate fabric using HT and pressure dyeing processes. Light and heat-fixable yellow dyeings are obtained.
Beispiel 2 Example 2
13,2 Teile des Amins der Formel siehe Zeichenblatt Nr. 2, Beispiel 2 a werden analog zu der in Beispiel 1 beschriebenen Arbeitsweise diazotiert. Nach Zerstören überschüssiger salpetriger Säure lässt man die Diazoniumsalzlösung zu einer auf 0°C abgekühlten Lösung von 7,1 Teilen l-Äthyl-2-hydroxy-3-cyan-4-methyl-pyridon-6 in 500 Raumteilen Wasser und 4 Teilen 50°/oiger Natronlauge laufen. Dabei wird durch Zugabe von verdünnter Natronlauge zum Kupplungsgemisch ein pH-Wert von 4,1 aufrecht erhalten. Nach Isolieren und Waschen wie üblich erhält man den Farbstoff der Formel siehe Zeichenblatt Nr. 1, Beispiel 2 b. Ausbeute: 19,8 Teile. 13.2 parts of the amine of the formula see drawing sheet No. 2, Example 2 a are diazotized analogously to the procedure described in Example 1. After excess nitrous acid has been destroyed, the diazonium salt solution is allowed to cool to a solution of 7.1 parts of l-ethyl-2-hydroxy-3-cyano-4-methyl-pyridone-6 cooled to 0 ° C. in 500 parts by volume of water and 4 parts of 50 ° / oiger caustic soda run. A pH of 4.1 is maintained by adding dilute sodium hydroxide solution to the coupling mixture. After isolation and washing as usual, the dye of the formula is obtained see drawing sheet No. 1, example 2 b. Yield: 19.8 parts.
Der Farbstoff färbt Polyäthylenterephthalatgewebe in lichtechten gelben Tönen von hoher Thermofixierechtheit. The dye dyes polyethylene terephthalate fabric in lightfast yellow tones of high heat-fastness.
Besonders bemerkenswert sind die hohe Baderschöpfung und Ausgiebigkeit des Farbstoffes. Particularly noteworthy are the high levels of bath exhaustion and the abundance of the dye.
Beispiel 3 Example 3
11,6 Teile der Diazokomponente der Formel siehe Zeichenblatt Nr. 2, Beispiel 3 a werden analog zu der in Beispiel 1 beschriebenen Arbeitsweise diazotiert und mit 7,1 Teilen l-Äthyl-2-hydroxy-3-cyan-4-methyöpyridon, die analog zu der in Beispiel 1 beschriebenen Arbeitsweise gelöst wurden, gekuppelt. 11.6 parts of the diazo component of the formula see drawing no. 2, Example 3 a are diazotized analogously to the procedure described in Example 1 and with 7.1 parts of l-ethyl-2-hydroxy-3-cyano-4-methyopyridone, which were solved analogously to the procedure described in Example 1, coupled.
Man erhält nach Absaugen, Waschen und Trocknen 18,5 Teile des Farbstoffs der Formel siehe Zeichenblatt Nr. 2, Beispiel 3 b. After suction, washing and drying, 18.5 parts of the dye of the formula are obtained, see drawing no. 2, example 3 b.
Der Farbstoff färbt Polyäthylenterephthalatgewebe in farbstarken, licht- und thermofixierechten gelben Tönen. The dye dyes polyethylene terephthalate fabric in strong yellow, lightfast and heat-fixable shades.
Analog erhält man auch die in den Tabellen siehe Zeichenblätter Nr. 3 bis 13, Beispiele 3 abis 113 durch Angabe der Substituenten charakterisierten Farbstoffe. The dyes characterized in the tables see drawing sheets No. 3 to 13, examples 3 to 113 by giving the substituents, are obtained analogously.
Beispiel Farbton Beispiel Farbton Example hue Example hue
3a gelb 3a yellow
7 7
gelb yellow
4 4th
gelb yellow
8 8th
gelb yellow
5 5
gelb yellow
9 9
gelb yellow
6 6
gelb yellow
10 10th
gelb yellow
Beispiel Farbton Beispiel Farbton Example hue Example hue
11 11
gelb yellow
63 63
gelb yellow
12 12
gelb yellow
64 64
gelb yellow
13 13
gelb yellow
65 65
gelb yellow
14 14
gelb yellow
66 66
gelb yellow
15 15
gelb yellow
67 67
gelb yellow
16 16
gelb yellow
68 68
gelb yellow
17 17th
gelb yellow
69 69
gelb yellow
18 18th
gelb yellow
70 70
gelb yellow
19 19th
gelb yellow
71 71
gelb yellow
20 20th
gelb yellow
72 72
gelb yellow
21 21st
gelb yellow
73 73
gelb yellow
22 22
gelb yellow
74 74
gelb yellow
23 23
gelb yellow
75 75
gelb yellow
24 24th
gelb yellow
76 76
gelb yellow
25 25th
gelb yellow
77 77
gelb yellow
26 26
gelb yellow
78 78
gelb yellow
27 27th
gelb yellow
79 79
gelb yellow
28 28
gelb yellow
80 80
gelb yellow
29 29
gelb yellow
81 81
gelb yellow
30 30th
gelb yellow
82 82
gelb yellow
31 31
gelb yellow
83 83
gelb yellow
32 32
gelb yellow
84 84
gelb yellow
33 33
gelb yellow
85 85
gelb yellow
34 34
gelb yellow
86 86
gelb yellow
35 35
gelb yellow
87 87
gelb yellow
36 36
gelb yellow
88 88
gelb yellow
37 37
gelb yellow
89 89
gelb yellow
38 38
gelb yellow
90 90
gelb yellow
39 39
gelb yellow
91 91
gelb yellow
40 40
gelb yellow
92 92
gelb yellow
41 41
gelb yellow
93 93
gelb yellow
42 42
gelb yellow
94 94
gelb yellow
43 43
gelb yellow
95 95
gelb yellow
44 44
gelb yellow
96 96
gelb yellow
45 45
gelb yellow
97 97
gelb yellow
46 46
gelb yellow
98 98
gelb yellow
47 47
gelb yellow
99 99
gelb yellow
48 48
gelb yellow
100 100
gelb yellow
49 49
gelb yellow
101 101
gelb yellow
50 50
gelb yellow
102 102
gelb yellow
51 51
gelb yellow
103 103
gelb yellow
52 52
gelb yellow
104 104
gelb yellow
53 53
gelb yellow
105 105
gelb yellow
54 54
gelb yellow
106 106
gelb yellow
55 55
gelb yellow
107 107
gelb yellow
56 56
gelb yellow
108 108
gelb yellow
57 57
gelb yellow
109 109
gelb yellow
58 58
gelb yellow
110 110
gelb yellow
59 59
gelb yellow
111 111
gelb yellow
60 60
gelb yellow
112 112
gelb yellow
61 61
gelb yellow
113 113
gelb yellow
62 62
gelb yellow
4 4th
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
ß ß
13 Blatt Zeichnungen 13 sheets of drawings
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2804599A DE2804599C2 (en) | 1978-02-03 | 1978-02-03 | Azo dyes, process for their preparation and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH637672A5 true CH637672A5 (en) | 1983-08-15 |
Family
ID=6031069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH94379A CH637672A5 (en) | 1978-02-03 | 1979-01-31 | Azo. |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS54132628A (en) |
| CH (1) | CH637672A5 (en) |
| DE (1) | DE2804599C2 (en) |
| FR (1) | FR2424303B1 (en) |
| GB (1) | GB2016501B (en) |
| IT (1) | IT1109777B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2910861A1 (en) * | 1979-03-20 | 1980-10-02 | Basf Ag | REACTIVE DYES |
| DE3244960A1 (en) * | 1982-12-04 | 1984-06-07 | Basf Ag, 6700 Ludwigshafen | PYRIDONE DYES |
| DE4227590A1 (en) * | 1992-08-20 | 1994-02-24 | Basf Ag | Azo dyes with a coupling component from the series of the N- (hydroxysulfonylphenylalkyl) pyridones |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2233871A1 (en) * | 1972-07-10 | 1974-02-14 | Basf Ag | AZO DYES WITH AN OXDIAZOLYL RESIDUE |
| DE2457687C3 (en) * | 1974-12-06 | 1979-01-04 | Basf Ag, 6700 Ludwigshafen | Azo dyes, their production and use for coloring lacquers, printing inks or plastics |
| DE2417217C3 (en) * | 1974-04-09 | 1980-07-03 | Basf Ag, 6700 Ludwigshafen | Pigment dyes with oxidazolyl residues, process for their preparation and their use |
| DE2432838A1 (en) * | 1974-07-09 | 1976-01-29 | Basf Ag | Azo pigments contg. an oxadiazolyl gp. - for use in paints, printing inks and plastics |
| DE2709660A1 (en) * | 1977-03-05 | 1978-09-07 | Basf Ag | SULPHONIC ACID GROUP-CONTAINING AZO DYES WITH OXDIAZOLYL RESIDUES |
-
1978
- 1978-02-03 DE DE2804599A patent/DE2804599C2/en not_active Expired
-
1979
- 1979-01-17 FR FR7901063A patent/FR2424303B1/en not_active Expired
- 1979-01-26 IT IT19655/79A patent/IT1109777B/en active
- 1979-01-31 CH CH94379A patent/CH637672A5/en not_active IP Right Cessation
- 1979-02-02 JP JP1052679A patent/JPS54132628A/en active Pending
- 1979-02-02 GB GB7903678A patent/GB2016501B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1109777B (en) | 1985-12-23 |
| FR2424303B1 (en) | 1985-06-14 |
| JPS54132628A (en) | 1979-10-15 |
| GB2016501B (en) | 1982-10-13 |
| IT7919655A0 (en) | 1979-01-26 |
| GB2016501A (en) | 1979-09-26 |
| FR2424303A1 (en) | 1979-11-23 |
| DE2804599A1 (en) | 1979-08-09 |
| DE2804599C2 (en) | 1983-03-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2304203C2 (en) | Disperse monoazo dyes, process for their preparation and their use for dyeing textile materials | |
| EP0244740B1 (en) | Diaminopyridine azo dyes with acyloxy groups | |
| DE2727383A1 (en) | AZO DYES OF THE PYRIDONE SERIES | |
| DE1644328A1 (en) | Process for the preparation of monoazo dyes | |
| CH616695A5 (en) | Process for the preparation of azo dyestuffs | |
| CH639119A5 (en) | AZOPIGMENTS. | |
| CH637672A5 (en) | Azo. | |
| DE2531445C3 (en) | Water-soluble azo dyes free of sulfo groups and their use for dyeing and / or printing synthetic textile fibers | |
| DE2333828A1 (en) | AZO DYES | |
| EP0197471B1 (en) | Azo dyes with thiophene diazo components | |
| DE2329133A1 (en) | DISPERSE MONOAZO DYES | |
| DE2612792A1 (en) | DISPERSE MONOAZO DYES | |
| DE2116315C3 (en) | Monoazo dyes, process for their preparation and use | |
| DE2743097C2 (en) | ||
| CH623601A5 (en) | ||
| DE2824710A1 (en) | HYDRO-INSOLUBLE MONOAZO DYES | |
| DE2544568C3 (en) | Azo dyes free of sulfonic acid groups, process for their production and their use as pigments in paints, printing inks or plastics | |
| CH637673A5 (en) | AZO DYES WITH THIAZOL RESIDUES. | |
| DE2910806A1 (en) | THIAZOL SERIES DYES | |
| DE2453209A1 (en) | DISAZO DYES | |
| DE1644074B2 (en) | Monoazo dyes containing sulfonic acid groups, processes for their production and dye preparations | |
| CH639404A5 (en) | Azo. | |
| DE1769503C (en) | Process for the production of water-insoluble aminoazo dyes | |
| DE2234348C3 (en) | Dyes of the pyrazole series, process for their preparation and their use for dyeing acid-modified polyamides, polyesters and acrylonitrile polymers | |
| DE2633909A1 (en) | DISPERSE MONOAZO DYES |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |