CH219931A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH219931A CH219931A CH219931DA CH219931A CH 219931 A CH219931 A CH 219931A CH 219931D A CH219931D A CH 219931DA CH 219931 A CH219931 A CH 219931A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- acid
- dye
- preparation
- amino
- 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 description 2
- 239000000975 dye Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 238000004043 dyeing Methods 0.000 claims description 4
- 210000002268 wool Anatomy 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- 239000000987 azo dye Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000001989 diazonium salts Chemical group 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 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 Darstellung eines ifonoazofarbstoffes. Monoazofarbstoffe der allgemeinen Formel
EMI0001.0003
EMI0001.0004
worin <SEP> X <SEP> eine <SEP> S02-, <SEP> S02NH- <SEP> oder <SEP> S02-N-Gruppe
<tb> I
<tb> alkyl bedeutet, mit unsubstituierten oder substituier ten Benzolkernen, sind in grosser Zahl be kannt geworden.
Es wurde nun gefunden, dass durch Ein führung einer Sulfonsäuregruppe in 3'-Stel- lung der Diazoniumverbindung Monoazofarb- stoffe der allgemeinen Formel
EMI0001.0013
erhalten werden, in welcher Formel X die oben angegebene Bedeutung besitzt und die beiden Benzolkerne auch weiter substituiert sein können, welche technisch sehr wertvoll sind.
Sie werden dargestellt durch Kuppeln von dianotierter 2 -Äminodiphenylsulfon- 3'- sulfonsäure und deren Substitutionsprodukten oder von dianotierter 2-Aminobenzol-l-sulfon- säure- N-phenylamid-3'- sulfonsäure bezw. 2 Aminobenzol-l-sulfonsäure-N-alkyl-N-phenyl- amid-3'-sulfonsäure mit 2-Amino-8-ogynaph- thalin-6-sulfonsäure in saurem Medium und gegebenenfalls Verseifung der
allenfalls vor handenen Acylaminogruppen in den erhal tenen Farbstoffen.
Durch die Einführung einer zweiten Sul- fonsäuregruppe ins Farbstoffmolekül, in 3' Stellung der Diazokomponente, erhält man überraschenderweise neue Farbstoffe von her vorragender Löslichkeit, die sich gegenüber den bekannten analogen monosulfonierten Farbstoffen vorteilhaft auszeichnen. Nicht nur zeigen die sauren Wollfärbungen kaum verändertes Egalisieren, sie sind zudem im allgemeinen etwas blauer und reiner und in der Lichtechtheit deutlich überlegen.
Ein der- artiger Einflur einer externen Sulfonsäure- gruppe ist neu und überraschend und war nicht vorauszusehen.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines No- noazofarbstoffes, welches dadurch gekenn zeichnet ist, dar diazotierte 2 - Amino - 5 - acetylaminobenzol-1- sulfonsäure- N -äthyl- N - phenylamid-3'-sulfonsä.ure in saurem 3Iedium mit 2-Amino - 8 - oxynaphthalin-6 -sulfonsäure gekuppelt wird.
Der neue Farbstoff, ein dunkelrotes Pul ver, liefert auf Wolle aus saurem Bade gleich mässige, blaustichigrote Färbungen, die sich durch sehr gute Lichtechtheit auszeichnen. <I>Beispiel:</I> 41,3 Teile 2-Amino-5-acetylaminobenzol- 1-sulfonsäure - N - äthyl- N -phenylamid- 3'-sul- fonsäure werden nach bekannten Methoden indirekt diazotiert. Die Diazoniumverbindung gibt man zu einer kongosauren Suspension von 24 Teilen 2-Aniilio-8-oxynaphtlialin-6- sulfonsäure und stumpft darauf die
Mineral säure in üblicher Weise bis zur schwach kongosauren Reaktion ab. Die Kupplung ist in kurzer Zeit beendet. Man erhält einen blauroten Farbstoff, der nach dem Filtrieren und Trocknen ein dunkelrotes Pulver bildet und auf Wolle aus saurem Bade gleichmässige, blaustichigrote Färbungen liefert, die sich durch sehr gute Lichtechtheit auszeichnen.
Process for the preparation of an ifonoazo dye. Monoazo dyes of the general formula
EMI0001.0003
EMI0001.0004
where <SEP> X <SEP> is a <SEP> S02-, <SEP> S02NH- <SEP> or <SEP> S02-N group
<tb> I.
<tb> alkyl means, with unsubstituted or substituted benzene nuclei, have become known in large numbers.
It has now been found that by introducing a sulfonic acid group in the 3'-position of the diazonium compound, monoazo dyes of the general formula
EMI0001.0013
are obtained in which formula X has the meaning given above and the two benzene nuclei can also be further substituted, which are technically very valuable.
They are produced by coupling dianotated 2-aminodiphenylsulphone-3'-sulphonic acid and its substitution products or of dianotated 2-aminobenzene-1-sulphonic acid-N-phenylamide-3'-sulphonic acid or. 2 aminobenzene-1-sulfonic acid-N-alkyl-N-phenyl-amide-3'-sulfonic acid with 2-amino-8-ogynaphthalene-6-sulfonic acid in an acidic medium and optionally saponification of the
at most any acylamino groups present in the dyes obtained.
By introducing a second sulfonic acid group into the dye molecule, in the 3 'position of the diazo component, surprisingly new dyes are obtained which have excellent solubility and which are advantageous over the known analogous monosulfonated dyes. Not only do the acidic wool dyeings show hardly any change in leveling, they are also generally somewhat bluer and purer and clearly superior in terms of lightfastness.
Such an input from an external sulfonic acid group is new and surprising and could not have been foreseen.
The subject of the present patent is a process for the production of a noazo dye, which is characterized in that diazotized 2-amino-5-acetylaminobenzene-1-sulfonic acid-N-ethyl-N-phenylamide-3'-sulfonic acid in acidic 3Iedium is coupled with 2-amino-8-oxynaphthalene-6-sulfonic acid.
The new dye, a dark red powder, supplies even, bluish-tinged red dyeings on wool from an acid bath, which are characterized by very good lightfastness. <I> Example: </I> 41.3 parts of 2-amino-5-acetylaminobenzene-1-sulfonic acid-N-ethyl-N-phenylamide-3'-sulfonic acid are indirectly diazotized by known methods. The diazonium compound is added to a Congo acid suspension of 24 parts of 2-Aniilio-8-oxynaphtlialin-6-sulfonic acid and then blunted
Mineral acid in the usual way up to the weak Congo acid reaction. The coupling is completed in a short time. A blue-red dye is obtained which, after filtering and drying, forms a dark red powder and, on wool from an acid bath, gives uniform, bluish-red dyeings which are distinguished by very good lightfastness.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH219931T | 1940-04-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH219931A true CH219931A (en) | 1942-03-15 |
Family
ID=4451405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH219931D CH219931A (en) | 1940-04-26 | 1940-04-26 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH219931A (en) |
-
1940
- 1940-04-26 CH CH219931D patent/CH219931A/en unknown
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