CH217487A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH217487A CH217487A CH217487DA CH217487A CH 217487 A CH217487 A CH 217487A CH 217487D A CH217487D A CH 217487DA CH 217487 A CH217487 A CH 217487A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- amine
- mixture
- preparation
- dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 2
- 239000013535 sea water Substances 0.000 claims description 2
- 210000004243 sweat Anatomy 0.000 claims description 2
- 238000009963 fulling Methods 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- -1 sweat Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Nonoazofarbstoffes. Es wurde gefunden, daB man wertvolle Monoazofarbstoffe, die Wolle aus saurem oder neutralem Bade in rotstickigen Farb tönen mit guten Echtheitseigenschaften fär ben, erhält, wenn man Diazoverbindungen von Aminen der allgemeinen Formel:
EMI0001.0006
worin X und Y gleiche oder verschiedene aliphatische, hydroaromatische oder aroma tische Reste bedeuten und der die Amino- gruppe tragende Benzolkern noch weitere Substituenten enthalten kann, mit N-Acyl- peri-aminoogynaphthalin-disuHonsäuren ver einigt.
Vorliegendes Patent bezieht sich nun auf ein Verfahren zur Herstellung eines Mono- azofarbstoffes, dadurch gekennzeichnet, daB man die Diazoverbindung eines Gemisches von Aminoverbindungen, das durch Reduk tion des Kondensationsproduktes von 1-Ni- trobenzol-4-carbonsäurechlorid mit einem Ge misch eines primären Amins der Formel:
EMI0001.0022
eines Amins der Formel:
EMI0001.0024
und eines Amins der Formel:
EMI0002.0001
erhalten wird, mit 1-(2',5'-Dichlorbenzoyl- amino),- 8 -ozynaphthalin - 4,6 - disulfonsäure vereinigt.
Der so erhaltene Farbstoff ist getrocknet ein wasserlösliches rotes Pulver und färbt Wolle in lebhaften gelbstichigen Rottönen von sehr guter Echtheit, insbesondere gegen Wäsche, Talke, Schweiss, Seewasser und Licht.
<I>Beispiel:</I> 34,6 Teile eines Gemisches von Amino- verbindungen, das durch Reduktion des Kon densationsproduktes von 1-Nitrobenzol-4-car- bonsäurechlorid mit einem Gemisch eines pri mären Amins der Formel:
EMI0002.0012
eines Amins der Formel:
EMI0002.0013
und eines Amins der Formel:
EMI0002.0014
erhalten wird, werden diazotiert. Die Diazo- verbindung gibt man zu einer Lösung von 50 Teilen 1-(2',5'-Dichlorbenzovlamino)-8- oxynaphthalin - 4,6 - disulfonsäure in Gegen wart eines Überschusses von Natriumkarbo nat. Der erhaltene Farbstoff wird abgeschie den und getrocknet.
Das oben erwähnte Gemisch von primären Aminen kann beispielsweise dadurch erhal ten werden, dass man ein Gemisch von Fett säuren mit 6 bis 8 gohlenstoffatomen, wie es technisch bei der Paraffinoxydation erhal ten wird, ketonisiert und auf das so erhaltene Ketongemisch Ammoniak und Wasserstoff oder Ammoniumformiat bezw. Formamid nach bekannter Arbeitsweise einwirken lässt.
Process for the preparation of a nonoazo dye. It has been found that valuable monoazo dyes, which dye wool from acidic or neutral baths in red-embroidered shades with good fastness properties, are obtained if diazo compounds of amines of the general formula:
EMI0001.0006
where X and Y are identical or different aliphatic, hydroaromatic or aromatic radicals and the benzene nucleus carrying the amino group may contain further substituents, united with N-acylperi-aminoogynaphthalene-disulfonic acids.
The present patent relates to a process for the preparation of a monoazo dye, characterized in that the diazo compound of a mixture of amino compounds obtained by reducing the condensation product of 1-nitrobenzene-4-carboxylic acid chloride with a mixture of a primary amine the formula:
EMI0001.0022
of an amine of the formula:
EMI0001.0024
and an amine of the formula:
EMI0002.0001
is obtained, combined with 1- (2 ', 5'-dichlorobenzoylamino), - 8 -ozynaphthalene - 4,6 - disulfonic acid.
The dyestuff obtained in this way is a water-soluble red powder when dried and dyes wool in vivid yellow-tinged red shades of very good fastness, in particular to laundry, talc, sweat, seawater and light.
<I> Example: </I> 34.6 parts of a mixture of amino compounds obtained by reducing the condensation product of 1-nitrobenzene-4-carboxylic acid chloride with a mixture of a primary amine of the formula:
EMI0002.0012
of an amine of the formula:
EMI0002.0013
and an amine of the formula:
EMI0002.0014
is obtained are diazotized. The diazo compound is added to a solution of 50 parts of 1- (2 ', 5'-dichlorobenzovlamino) -8-oxynaphthalene-4,6-disulfonic acid in the presence of an excess of sodium carbonate. The dye obtained is deposited and dried.
The above-mentioned mixture of primary amines can be obtained, for example, by ketonizing a mixture of fatty acids with 6 to 8 carbon atoms, as is technically obtained in paraffin oxidation, and adding ammonia and hydrogen or ammonium formate to the resulting ketone mixture . Let formamide take effect according to a known working method.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE217487X | 1938-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH217487A true CH217487A (en) | 1941-10-31 |
Family
ID=5830773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH217487D CH217487A (en) | 1938-12-23 | 1939-12-18 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH217487A (en) |
-
1939
- 1939-12-18 CH CH217487D patent/CH217487A/en unknown
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