DE653026C - Process for the preparation of monoazo dyes - Google Patents
Process for the preparation of monoazo dyesInfo
- Publication number
- DE653026C DE653026C DEG91413D DEG0091413D DE653026C DE 653026 C DE653026 C DE 653026C DE G91413 D DEG91413 D DE G91413D DE G0091413 D DEG0091413 D DE G0091413D DE 653026 C DE653026 C DE 653026C
- Authority
- DE
- Germany
- Prior art keywords
- oxybenzene
- dyes
- monoazo dyes
- preparation
- monoazo
- 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.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 21
- 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 10
- 238000000034 method Methods 0.000 title claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000004382 potting Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von Monoazofarbstoffen Es wurde gefunden, daß man auf der Faser nach allen üblichen Arbeitsweisen chromierbare Monoazofarbstoffe von ausgezeichneten Echtheitseigenschaften erhält, wenn man die Diazoverbindung aus 4-Nitro-2-amino-i-.oxybenzol-6-sulfonsä,ure mit Phenolen kuppelt, die in 4-Stellung,durch eine Alkylgruppe mit mindestens 3 und höchstens 5 Kohlenstoffatomen substituiert sind. Die neuen Farbstoffe sind dunkle Pulver. Sie färben Wolle aus saurem Bade in gelbbraunen Tönen, die durch Chromieren in wertvolle, satte und gedeckte Brauntöne von vorzüglichen Echtheitseigenschaften übergehen.Process for the production of monoazo dyes It has been found that chromable monoazo dyes are used on the fiber by all customary procedures of excellent fastness properties when using the diazo compound from 4-nitro-2-amino-i-.oxybenzene-6-sulfonic acid with phenols that couple in the 4-position through an alkyl group having at least 3 and at most 5 carbon atoms is substituted are. The new dyes are dark powders. They dye wool from an acid bath in yellow-brown tones, which by chroming in valuable, rich and muted brown tones go over from excellent fastness properties.
In 4-Stellung höher alkylierte Phenole wurden bis jetzt nicht zur Herstellung von o-Oxyazofarbstoffen verwendet. Es wurde gefunden, daß sie, obwohl sie schlechter kuppeln als z. B. 4-Methyl-i-@oxybenzol, dennoch in zufriedenstellender Ausbeute mit diazotlerter 4-Nitro-2-amino-i--oxybenzol-6-sulfonsä#ure sich zu wertvollen, chromierbären Monioazofarbstoffen vereinigen lassen. Es ließ sich überhaupt nicht voraussagen, ob die in 4-Stellung durch höhere Alkylgruppen substituierten Phenole, wie beispielsweise das heute technisch zugängliche 4-tertiäre Amyl-i-oxybenzol, noch mit diazotierten Nitnoaminophenolen kuppeln würden. Eher mußte das Gegenteil erwartet werden, da bis heute keine o-Oxyazofarbstoffe mit diesen Alkylphenolhomponenten bekanntgeworden sind.Phenols higher alkylated in the 4-position have not been used until now Used in the manufacture of o-oxyazo dyes. It was found that she did, though they couple worse than z. B. 4-methyl-i- @ oxybenzene, but in a more satisfactory manner Yield with diazotized 4-nitro-2-amino-i-oxybenzene-6-sulfonic acid turns into valuable, Let chromable monioazo dyes combine. It didn't work at all predict whether the phenols substituted in the 4-position by higher alkyl groups, such as the 4-tertiary amyl-i-oxybenzene, which is technically available today, would still couple with diazotized nitnoaminophenols. It had to be the opposite are expected, since to date no o-oxyazo dyes with these alkylphenol components have become known.
Monoazofarbstoffe aus diazotierten,o-Aminophenolen und p-alkylsubstituierten Phenolen sind schon in einigen Fällen bekanntgewor= den (vgl. die Patentschriften 21o964, 291q.99, 344322, 351 001, 541 195 und 541 196). Vor diesen bekannten Farbstoffen zeichnen sich die nach vorliegendem Verfahren erhältlichen Farbstoffe durch folgende bessere Echtheitseigenschaften aus: der Monoamfarbstoff aus diazotierter 4 - Nitro - 2 - amino - i - @oxybenzol-6-sulfonsäure und 4-tertiärem Amyl-i-oxybenzol ist pottingechter und etwas besser lichtecht als der entsprechende MonoazofarbstOff mit 4-Methyl-i-oxybenzol als Azokomponente (Patentschrift 541 195). "Gegenüber dem Monoazofarbstoff aus der gleichen Diazokomponente und 2, 4-Dimethyl-i-oxybenzol (as./m-Xylenol, Patentschrift 541 195) ist der obenerwähnte neue Monoazofarbstoff potting-und lichtechter. Monoazofarbstoffe, die als Azokompionente 4-Oxydiphenylmethan (Patentschrift 541 195) enthalten, sind teils weniger lichtecht, teils egalisieren sie .bedeutend schlechter und eignen sich weniger gut zum Färben im Einbadchromverfahren mit Chromat oder Bichromat.Monoazo dyes from diazotized, o-aminophenols and p-alkyl-substituted Phenols are already known in some cases (cf. the patents 21o964, 291q.99, 344322, 351 001, 541 195 and 541 196). Before these known dyes the dyes obtainable by the present process are distinguished by the following better fastness properties from: the monoam dye from diazotized 4-nitro - 2 - amino - i - @ oxybenzene-6-sulfonic acid and 4-tertiary amyl-i-oxybenzene More potting and slightly better lightfast than the corresponding monoazo dye with 4-methyl-i-oxybenzene as the azo component (patent 541 195). "Compared to the Monoazo dye from the same diazo component and 2,4-dimethyl-i-oxybenzene (as./m-Xylenol, patent 541 195) is the new monoazo dye mentioned above potting and lightfast. Monoazo dyes used as azo component 4-oxydiphenylmethane (Patent specification 541 195) are sometimes less lightfast, in some cases they equalize. Significantly worse and are less suitable for dyeing in the single bath chrome process with chromate or bichromate.
Beispiel i 23,4 kg 4-Nitro-2-amino-i,oxybenzol-6-sul-' fonsäure werden in bekannter Weise diazotiert. Die überschüssige Mineralsäure wird mit Bicarbonat abgestumpft, und die DiazoniumIösung wird unter Rühren einer Lösungvon 16,5 kg 4-tertiärem Amyl-i-oxybenzolund 6 kg festem Kaliumhydroxyd in 5o 1 Wasser zugesetzt. Nach beendeter Kupplung wird der Monoazofarbstoff ausgesalzen, abfrltriert und getrocknet. Die Farbstoffbildung verläuft etwas schneller in Gegenwart von Pyridin.Example i 23.4 kg of 4-nitro-2-amino-i, oxybenzene-6-sulphonic acid become diazotized in a known manner. The excess mineral acid is made with bicarbonate blunted, and the diazonium solution is stirred with a solution of 16.5 kg of 4-tertiary Amyl-i-oxybenzene and 6 kg of solid potassium hydroxide in 50 l of water were added. After finished Coupling, the monoazo dye is salted out, filtered off and dried. the Dye formation is somewhat faster in the presence of pyridine.
Der Farbstoff bildet ein braunes Pulver, das sich in Wasser und konzentrierter Schwefelsäure mit gelbbrauner Farbe löst. Beispiel 2 Verwendet man statt der in Beispiel i angegebenen Menge an 4-tertiärem Amyl-r-oxy-@enzo@ zur Kupplung mit der gleichen Diazof»mlösung 13,5 kg 4-Isopropyl-i-oxybenzol öder 15 kg 4-Butyl-i-oxybenzol, so erhält man in gleicher Weise braune Chrommonoavofarbstoffe von ähnlichen ausgezeichneten Echtheitseigenschaften.The dye forms a brown powder that is concentrated in water and Sulfuric acid dissolves with a yellow-brown color. Example 2 If instead of the in Example i specified amount of 4-tertiary amyl-r-oxy- @ enzo @ for coupling with the the same diazo solution 13.5 kg 4-isopropyl-i-oxybenzene or 15 kg 4-butyl-i-oxybenzene, thus brown chromium monoavo dyes of similar excellent ones are likewise obtained Authenticity properties.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH653026X | 1934-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE653026C true DE653026C (en) | 1937-11-12 |
Family
ID=4526268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG91413D Expired DE653026C (en) | 1934-11-05 | 1935-10-26 | Process for the preparation of monoazo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE653026C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE762567C (en) * | 1942-05-05 | 1953-03-30 | Geigy Ag J R | Process for the preparation of o-oxyazo dyes |
-
1935
- 1935-10-26 DE DEG91413D patent/DE653026C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE762567C (en) * | 1942-05-05 | 1953-03-30 | Geigy Ag J R | Process for the preparation of o-oxyazo dyes |
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