CH402234A - Process for the production of a red wool dye - Google Patents
Process for the production of a red wool dyeInfo
- Publication number
- CH402234A CH402234A CH718362A CH718362A CH402234A CH 402234 A CH402234 A CH 402234A CH 718362 A CH718362 A CH 718362A CH 718362 A CH718362 A CH 718362A CH 402234 A CH402234 A CH 402234A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- production
- red
- wool
- good
- Prior art date
Links
- 210000002268 wool Anatomy 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 7
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000975 dye Substances 0.000 description 18
- 238000004043 dyeing Methods 0.000 description 5
- 239000000835 fiber Substances 0.000 description 4
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical group C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BBDNZMUIQBRBJH-UHFFFAOYSA-N sulfurochloridic acid;toluene Chemical compound OS(Cl)(=O)=O.CC1=CC=CC=C1 BBDNZMUIQBRBJH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/24—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with formation of —O—SO2—R or —O—SO3H radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines roten Wollfarbstoffes Es ist bekannt, dass man rotfärbende Wollfarb- stoffe dadurch herstellen kann, indem man z.
B. den Disazofarbstoff aus tetrazotiertem 4,4'-Diamino-3,3'- dimethyldiphenyl(o-tolidin), 2 Naphtholdisulfonsäure- 6,8 und Phenol mit Benzol- bzw. Toluolsulfochlorid verestert. Solche rotfärbenden Wollfarbstoffe zeichnen sich in der Regel durch gute Echtheiten aus, wobei besonders die Nassechtheiten zu erwähnen sind. Die Nuance ist klar und von guter Lichtechtheit.
Solche Farbstoffe färben in der Regel aus sauren bzw. schwachsauren Bädern animalische Fasern, insbeson dere Wolle an. Für den Einsatz zum Färben von Wolle, Baumwolle, Mischgeweben und. Gespinsten sind sie nicht immer geeignet, da ihr neutrales Ziehvermögen für diesen Verwendungszweck oft unzureichend ist.
Es wurde nun gefunden, dass man einen rotfär benden Wollfarbstoff erhält, der sehr gut. aus neutralen Bädern auf animalische Fasern, insbesondere Wolle, zieht, wenn :man den Disazofarbstoff folgender Kon stitution
EMI0001.0040
mit p-Chlorbenzolsulfonsäurecblorid verestert. Der resultierende Farbstoff,- der folgende Konstitution be sitzt:
EMI0001.0045
färbt animalische Fasern, insbesondere Wolle, in einer brillanten, roten Nuance.
Sein Ziehvermögen aus neu traler Flotte ist sehr gut und bekannten ähnlichen Farbstoffen überlegen. Es ist besonders zum Färben von Halbwollfarbstoffsteilungen geeignet.
Hervorzuhe ben von den im allgemeinen guten Echtheiten sind. besonders die guten Nassechtheiten. Der Einbau eines zusätzlichen Chloratoms in das anfangs aufgezeich nete Farbstoffmolekül erbrachte eine Steigerung des Ziehvermögens aus neutralem Bade, wie es nicht vor ausgesehen werden konnte. <I>Beispiel</I> 63,2 Teile des Disazofarbstoffes,
wie er durch Kuppeln von tetrazotiertem o-Tolidin erst mit 2 Naph- tholdisulfonsäure-6,8 und anschliessend mit Phenol erhalten wird, werden in Wasser eingetragen und auf etwa<B>65-70'</B> C erwärmt. Anschliessend trägt man rasch etwa 25 Teile p-Chlorbenzolsulfochlorid ein und tropft Sodalösung in der Weise zu, dass immer ein pH-Wert von 7,5-8 resultiert. Man lässt so lange reagieren, bis eine verdünnte Probe mit Essigsäure keinen Farbumschlag mehr zeigt.
Dann erhitzt man kurz auf 90 C und salzt mit etwa 15 % NaCl aus. Bei 90 C filtriert man den kristallin. ausgefallenen Farbstoff ab. Er stellt getrocknet ein dunkelrotes Pul ver dar, das animalische Fasern, insbesondere Wolle, bereits aus neutraler Flotte in guten Echtheiten färbt.
Auf Grund des sehr guten neutralen Ziehvermögens und der guten Echtheitseigenschaften ist dieser Farb stoff besonders zum Einstellen von roten Halbwoll- farbstoffen geeignet.
Process for the production of a red wool dye It is known that red-dyeing wool dyes can be produced by z.
B. esterified the disazo dye from tetrazotized 4,4'-diamino-3,3'-dimethyldiphenyl (o-tolidine), 2 naphthol disulfonic acid 6,8 and phenol with benzene or toluenesulfochloride. Such red-dyeing wool dyes are generally distinguished by good fastness properties, the wet fastness properties being particularly worthy of mention. The shade is clear and has good lightfastness.
Such dyes usually dye animal fibers, in particular wool, from acidic or weakly acidic baths. For use in dyeing wool, cotton, blended fabrics and. They are not always suitable for webs, since their neutral drawability is often insufficient for this purpose.
It has now been found that a red dyeing wool dye is obtained which is very good. from neutral baths on animal fibers, especially wool, pulls if: one stitution disazo dye of the following constitution
EMI0001.0040
Esterified with p-chlorobenzenesulfonic acid chloride. The resulting dye - has the following constitution:
EMI0001.0045
dyes animal fibers, especially wool, in a brilliant red shade.
Its drawability from neutral liquor is very good and superior to known similar dyes. It is particularly suitable for dyeing semi-wool dye divisions.
The generally good fastness properties should be emphasized. especially the good wet fastness properties. The incorporation of an additional chlorine atom into the dye molecule initially recorded resulted in an increase in the drawability from a neutral bath that could not have been anticipated before. <I> Example </I> 63.2 parts of the disazo dye,
as obtained by coupling tetrazotized o-tolidine first with 2-naphthol-6,8 and then with phenol, are added to water and heated to about 65-70 ° C. Then about 25 parts of p-chlorobenzenesulfonyl chloride are quickly introduced and soda solution is added dropwise in such a way that a pH of 7.5-8 is always obtained. The reaction is allowed to take place until a diluted sample with acetic acid no longer changes color.
Then it is heated briefly to 90 ° C. and salted out with about 15% NaCl. The crystalline is filtered off at 90 ° C. precipitated dye. When dried, it is a dark red powder that dyes animal fibers, especially wool, with good fastness properties even from a neutral liquor.
Due to the very good neutral drawability and the good fastness properties, this dye is particularly suitable for setting red semi-wool dyes.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD7812662 | 1962-02-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH402234A true CH402234A (en) | 1965-11-15 |
Family
ID=5477710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH718362A CH402234A (en) | 1962-02-08 | 1962-06-13 | Process for the production of a red wool dye |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH402234A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2214685A1 (en) * | 1973-01-18 | 1974-08-19 | Ugine Kuhlmann | |
| WO1994004613A1 (en) * | 1992-08-14 | 1994-03-03 | Zeneca Limited | Watersoluble disazodyes for dyeing leather |
-
1962
- 1962-06-13 CH CH718362A patent/CH402234A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2214685A1 (en) * | 1973-01-18 | 1974-08-19 | Ugine Kuhlmann | |
| WO1994004613A1 (en) * | 1992-08-14 | 1994-03-03 | Zeneca Limited | Watersoluble disazodyes for dyeing leather |
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