DE133714C - - Google Patents
Info
- Publication number
- DE133714C DE133714C DENDAT133714D DE133714DA DE133714C DE 133714 C DE133714 C DE 133714C DE NDAT133714 D DENDAT133714 D DE NDAT133714D DE 133714D A DE133714D A DE 133714DA DE 133714 C DE133714 C DE 133714C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- green
- blue
- dyes
- solution
- 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.)
- Active
Links
- 239000000975 dye Substances 0.000 claims description 13
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 10
- 150000008049 diazo compounds Chemical class 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 229960004889 salicylic acid Drugs 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- -1 polyazo Polymers 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000001808 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- FBMPKWAJWSPYLS-UHFFFAOYSA-N (4-nitrophenyl)sulfamic acid Chemical compound OS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1 FBMPKWAJWSPYLS-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical class NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000010186 staining Methods 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
- C09B35/463—D being derived from diaminodiphenyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHES 7i IMPERIAL 7i
PATENTAMT.PATENT OFFICE.
Die Diazoverbindungen der p-Nitranilin-osulfosäüre bezw. -o-carbonsäure sind bisher zur Darstellung von Azofarbstoffen technisch nicht verwendet worden. Im Verfolg der Untersuchungen über diese beiden leicht zugänglichen Diazoverbindungen ist die Erfinderin zur Darstellung weiterer höchst werthvoller Polyazofarbstoffe gelangt. Läfst man nämlich auf den aus diesen Diazoverbindungen mit der Amidonaphtoldisulfosäure K dargestellten o-Amidoazofarbstoff moleculare Mengen Tetrazodiphenyl einwirken und combinirt das entstandene Zwischenproduct mit Phenolen oder dessen Carbonsäuren, so erhält man Farbstoffe,, die Baumwolle ohne Beize in kochsalzhalligein alkalischen Bade grün bis blaugrün färben. Gegenüber den analog zusammengesetzten Farbstoffen aus dem nicht substituirten p-Nitranilin (vcrgl. engl. Patent 515/94) sind die nach dem gekennzeichneten Verfahren dargestellten durch gröfsere Löslichkeit ausgezeichnet. Während die Farbstoße des englischen Patentes in dem Färbebade ausfallen und unegale Färbungen erzeugen, erhält man mit den neuen Farbstoffen sehr schöne egale Nuancen, die zudem noch gegenüber dem Farbstoff Diamingrün des Handels (D. R. P. 66351) durch bessere Licht- und Alkaliechtheit ausgezeichnet sind.The diazo compounds of p-nitroaniline-sulfonic acid respectively -o-carboxylic acids have not yet been used technically for the preparation of azo dyes been used. In pursuit of the research on these two easily accessible Diazo compounds is the inventor for the preparation of other highly valuable ones Polyazo dyes. If you run on the diazo compounds from these of the amidonaphthol disulfonic acid K represented o-amidoazo dye molecular amounts of tetrazodiphenyl act and combine the resulting intermediate product with phenols or their carboxylic acids, one obtains dyes, dye the cotton green to blue-green in an alkaline bath without staining. Compared to the similarly composed dyes from the unsubstituted p-nitroaniline (cf. English Patent 515/94) are those according to characterized by greater solubility. While the dyes of the English patent fail in the dye bath and uneven dyeings produce, you get very nice level nuances with the new dyes, which also compared to the commercial diamine green dye (D. R. P. 66351) due to better light and alkali fastness are excellent.
i. 24 kg ρ nitranilinsulfosaures Natron werden in 500 1 heifsen Wassers gelöst, nach dem Kühlen mit Eis mit 6,9 kg Nitrit vermischt und in 30 kg mit Eiswasser verdünnter Salzsäure einlaufen gelassen. Die Diazotirung findet momentan statt, wobei sich die Diazoverbindung theilweise in krystallinischer Form ausscheidet. Hierzu läfst man nun eine Lösung von 34,1 kg des sauren Natriumsalzes der K-Säure und 5,5 kg Soda in 800 1 Wasser laufen und rührt mehrere Stunden, bis die Kupplung beendigt ist. Man fügt nun eine Lösung von 100 kg krystallisirtem Natriumacetat hinzu, worauf man eine aus 18,4 kg Benzidin in der üblichen Weise hergestellte Tetrazolösung einlaufen läfst. Die Bildung des Zwischenproductes ist nach einigem Rühren beendigt. Man lafst nun in eine Lösung von 15 kg Salicylsäure in 50 kg Natronlauge und 1500 I Wasser, der aufserdem noch 50 kg Soda zugesetzt wurden, einlaufen, nach mehreren Stunden wärmt man an und fällt den Farbstoff mit Salz, filtrirt, prefst und trocknet.i. 24 kg ρ nitranilinsulfosaures soda become dissolved in 500 liters of hot water, mixed with 6.9 kg of nitrite after cooling with ice and allowed to run into 30 kg of hydrochloric acid diluted with ice water. The diazotization takes place momentarily taking place, the diazo compound partly precipitating out in crystalline form. For this purpose, a solution of 34.1 kg of the acidic sodium salt of the K-acid is now allowed Run 5.5 kg of soda in 800 l of water and stir for several hours until the coupling has ended is. A solution of 100 kg of crystallized sodium acetate is then added, whereupon a tetrazo solution prepared in the usual way from 18.4 kg of benzidine runs in. The formation of the intermediate product is complete after some stirring. Now let in a solution of 15 kg of salicylic acid in 50 kg of sodium hydroxide solution and 1500 l of water, which also 50 kg of soda were added, run in, after several hours warm up and the dye is precipitated with salt, filtered, prefilled, and dried.
2. 21 kg nitranilincarboiisaures Natron -werden in 500 1 heifsen Wassers gelöst, mit Eis gekühlt und nach dem Vermischen mit 7 kg Nitrit in 42 kg mit Eiswasser verdünnter Salzsäure einlaufen gelassen. Nachdem die Nitritreaction verschwunden und die Diazotirung event, noch durch Zusatz kleiner Nitritmengen zu Ende geführt ist, läfst man eine Lösung von 34,1 kg des sauren Natriumsalzes der K-Säure und 5,5 kg Soda in 800 1 Wasser einlaufen und rührt, bis die Kupplung beendigt ist. Man versetzt das so erhaltene Zwischenproduct sodann mit 100 kg Natriumacetat und läfst die aus 18,4 kg Benzidin in der üblichen Weise erhaltene Tetrazolösung einlaufen. Sobald kein Tetrazodiphenyl mehr nachzuweisen ist, fügt man eine kalte Lösung von 15 kg Salicylsäure in 50 kg Natronlauge und 500 1 Wasser hinzu. Nach einigem Rühren ist die2. 21 kg of nitraniline carbonate of soda become dissolved in 500 l of hot water, cooled with ice and after mixing with 7 kg Nitrite poured into 42 kg of hydrochloric acid diluted with ice water. After the nitrite reaction disappeared and the diazotization event, still through the addition of small amounts of nitrite is completed, a solution of 34.1 kg of the acidic sodium salt of the Run K-acid and 5.5 kg of soda in 800 l of water and stir until the coupling has ended is. The intermediate product thus obtained is then mixed with 100 kg of sodium acetate and The tetrazo solution obtained from 18.4 kg of benzidine runs in the usual way. As soon as no more tetrazodiphenyl can be detected a cold solution of 15 kg of salicylic acid in 50 kg of sodium hydroxide solution and 500 l Add water. After some stirring it is
Farbstoff bildung beendigt. Der neue Trisazofarbstoff ist ganz gelöst und wird durch Anwärmen und Aussalzen gewonnen. WennDye formation ended. The new trisazo dye is completely dissolved and is made by heating and salting out. if
nöthig, so kann er durch Auswaschen mit Salzwasser oder durch Auflösen in heifsem Wasser und abermaliges Aussalzen gereinigt werden.if necessary, it can be washed out with salt water or by dissolving in hot water and again salting out be cleaned.
sehenthe end
see
in
Wassersolution
in
water
Zusatz
von
Salzsäureon
additive
from
hydrochloric acid
Zusatz
von
Natron
laugeon
additive
from
Baking soda
lye
in
Schwefel
säuresolution
in
sulfur
acid
Zusatz
von
Wasseron
additive
from
water
auf
Baum
wollecoloring
on
tree
wool
Benzidin<f sulfosäure
.xPhenolK-acid-p-nitroaniline-
Benzidine <f sulfonic acid
. x phenol
bronziges
PulverBrown-
bronzy
powder
' Nieder
schlagbluer
'Down
blow
Fällungblack
precipitation
blauviolet
blue
Nieder
schlagbluer
Low
blow
Benzidin^ sulfosäure
SalicylsäureK-acid-p-nitroaniline-
Benzidine ^ sulfonic acid
Salicylic acid
desgl.the same
the same
grüne
■ Fällungtheihveise
green
■ precipitation
schwarzviolet
black
violett-blue
violet-
schwarzer
Nieder
schlag
blnu-
schwiirzcr
■Nieder-,
schlaggreen
black
Low
blow
blnu-
blacker
■ low,
blow
Benzidin^ sullnslturc
p-Oxy-o-toluylsllureK-Sllure-p-Nitninilin-
Benzidine ^ sullnslturc
p-Oxy-o-toluic acid
schwnrzer
Nieder
schlugblue-
blacker
Low
hit
Nieder
schlagpurple
Low
blow
Benzidin/ carbonsiiure
^Phenol"K-acid-p-nitroaniline-
Benzidine / carboxylic acid
^ Phenol "
schwarzer
Nieder
schlagviolet-
black
Low
blow
schwarzer
Nieder
schlaggreen
black
Low
blow
Benzidin<f . carbonsäure
Salicylsäure· ■ K-Acid-p-NitraniKn-
Benzidine <f. carboxylic acid
Salicylic acid
schwarzer
Nieder
schlaggreen
black
Low
blow
blauviolet
blue
schwarzer
Nieder
schlagblue
black
Low
blow
Benzidin^ carbonsäure
p-Oxy-o-toluylsäureK-acid-p-nitroaniline-
Benzidine ^ carboxylic acid
p-oxy-o-toluic acid
schwarzer
Nieder
schlagblue
black
Low
blow
Claims (1)
Publications (1)
Publication Number | Publication Date |
---|---|
DE133714C true DE133714C (en) |
Family
ID=401894
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT133714D Active DE133714C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE133714C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4685469A (en) * | 1984-03-09 | 1987-08-11 | Keller Hans W | Piezoresistive pressure measuring cell |
-
0
- DE DENDAT133714D patent/DE133714C/de active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4685469A (en) * | 1984-03-09 | 1987-08-11 | Keller Hans W | Piezoresistive pressure measuring cell |
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