DE134163C - - Google Patents
Info
- Publication number
- DE134163C DE134163C DENDAT134163D DE134163DA DE134163C DE 134163 C DE134163 C DE 134163C DE NDAT134163 D DENDAT134163 D DE NDAT134163D DE 134163D A DE134163D A DE 134163DA DE 134163 C DE134163 C DE 134163C
- Authority
- DE
- Germany
- Prior art keywords
- yellow
- brown
- brownish
- red
- cresol
- 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
- 239000002253 acid Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 210000002268 Wool Anatomy 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N P-Cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N O-Cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims 5
- 235000019233 fast yellow AB Nutrition 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 240000002799 Prunus avium Species 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- 235000019693 cherries Nutrition 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- YARIFRHBFXEJNY-UHFFFAOYSA-N 3-hydroxy-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1O YARIFRHBFXEJNY-UHFFFAOYSA-N 0.000 description 1
- 230000036826 Excretion Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical class [N-]=[N+]=[*] 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000983 mordant dye Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
-JV* 134163 KLASSE 22 a. -JV * 134163 CLASS 22 a.
In der Patentschrift 134162 ist eine Reihe von Beizenfarbstoffen beschrieben, welche durch Vereinigung von diaz. o-Amidophenol und dessen Substitutionsproducten bezw. 2 · 3 Amidonaphtol-6-sulfosäure mit 1 -Phenyl-5-Pyrazoloh und seinen Derivaten entstehen. Es hat sich nun weiter ergeben, dafs gewisse Substitutionsproducte des o-Amidophenols nach dem Verfahren des Haupt-Patentes cömbinirt Farbstoffe liefern, welche gegenüber den im Haupt-Patent angeführten Ausführungsformen durch die Schönheit der blaueren Nuance einen erheblichen technischen Fortschritt darstellen. Diese Substitutionsproducte sind die 3-Amido-2-kresol-5-sulfosäure, 3-Amido-4-kresol-5-sulfosäure, 3-Amido-4-kresol-6-sulfosäure. 'In patent specification 134162 there is a series of mordant dyes described, which by association of diaz. o-amidophenol and its substitution products respectively. 2 x 3 amidonaphthol-6-sulfonic acid with 1-phenyl-5-pyrazolo and its derivatives. It It has now also been found that certain substitution products of the o-amidophenol are after the process of the main patent combines dyes which, compared with the im Main patent cited embodiments through the beauty of the bluer shade one represent considerable technical progress. These substitution products are 3-amido-2-cresol-5-sulfonic acid, 3-amido-4-cresol-5-sulfonic acid, 3-amido-4-cresol-6-sulfonic acid. '
Die 3-Amido-2-kresol-5-sulfosäure wird aus der 2-Kresol-5-sulfosäure (Ber.XX, 3210) durch Nitrirung und Reduction der Mononitroverbindung erhalten.The 3-amido-2-cresol-5-sulfonic acid is derived from the 2-cresol-5-sulfonic acid (Ber.XX, 3210) Nitration and reduction of the mononitro compound obtained.
Die 3-Amido-4-kresol-5-sulfosäure entsteht in analoger Weise aus der 4-Kresol-5(3)-sulfosäure (Zeitschrift für Chemie 1869, 619; Ann. 173, 203) und die .The 3-amido-4-cresol-5-sulfonic acid is produced in an analogous manner from the 4-cresol-5 (3) -sulfonic acid (Journal of Chemistry 1869, 619; Ann. 173, 203) and the.
3-Amido-4-kresol-6-sulfosäure ebenso aus der 4-Kresol-6(2)-sulfosHure (Ann, 172, 237).3-Amido-4-cresol-6-sulfonic acid also from 4-cresol-6 (2) -sulfosHure (Ann, 172, 237).
Alle drei Aminosäuren sind ungefärbte Substanzen ; die freien Säuren sind ziemlich schwer löslich in kaltem Wasser und lassen sich aus heifsem Wasser umkrystallisiren. Ihre Diazoverbindungen sind gelb gefärbt; die der ersten und zweiten Säure sind leichter löslich als die der dritten. All three amino acids are uncolored substances ; the free acids are rather sparingly soluble in cold water and can be left out recrystallize hot water. Their diazo compounds are colored yellow; that of the first and second acids are more soluble than those of the third.
Die Darstellung der Farbstoffe erfolgt ganz nach dem Verfahren des Haupt-Patentes.The representation of the dyes follows the procedure of the main patent.
112,5 Th. 3-Amido-4-kresol-5-sulfosaures Natron werden in 1000 Th. Wasser gelöst und bei ca. io° C. 500 Th. verdünnte kalte Salzsäure, welche 135 Th. Salzsäure von 190B. enthält, eingegossen. Hierbei scheidet sich die freie Amidokresolsulfosäure aus. Durch Zusatz von 35 Th. Nitrit geht die Ausscheidung in Form der gelben Diazoverbindung in Lösung. Diese Diazolösung läfst man einfliefsen in eine Auflösung von 91 Th. i-Phenyl-3-methyl-5-pyrazolon nebst 22 Th. Aetznatron und 55 Th. Soda in 2000 Th. Wasser. Die Kuppelung ist nach mehrstündigem Rühren bei gewöhnlicher Temperatur beendet; der Farbstoff ist bei dieser Temperatur nicht gelöst. Er stellt ein orangefarbenes Pulver dar und färbt Wolle gelb. Durch Chromirung geht die gelbe Färbung in Roth über, welchem vortreffliche Echtheitseigenschaften zukommen. 112.5 Th. 3-amido-4-cresol-5-sulfosaures soda are dissolved in 1000 Th. And water at about 500 ° C io Th. Dilute cold hydrochloric acid which 135 Th. Hydrochloric acid of 19 0 B. contains , poured. The free amidocresol sulfonic acid is precipitated here. By adding 35 parts of nitrite, the excretion goes into solution in the form of the yellow diazo compound. This diazo solution is run into a solution of 91 parts of i-phenyl-3-methyl-5-pyrazolone together with 22 parts of caustic soda and 55 parts of soda in 2000 parts of water. The coupling is completed after several hours of stirring at ordinary temperature; the dye is not dissolved at this temperature. It is an orange powder and dyes wool yellow. Chromation turns the yellow coloration into red, which has excellent fastness properties.
Claims (1)
4-kresol-
5-sulfo-
säure
(diaz.)
+ 3-amido
4-cresol
5-sulfo-
acid
(diaz.)
+
2-kresol-
5-sulfo-
säure
(diaz.)
+ 3-amido
2-cresol
5-sulfo-
acid
(diaz.)
+
4-kresol-
6-sulfo-
säure
(diaz.)
+ 3-amido
4-cresol
6-sulfo-
acid
(diaz.)
+
4-kresol-
5-sulfo-
säure
(diaz.)
+ 3-amido
4-cresol
5-sulfo-
acid
(diaz.)
+
2-kresol-
6-sulfo-
säure
(diaz.)
+ 3-amido
2-cresol
6-sulfo-
acid
(diaz.)
+
4-kresol-
6-sulfo-
säure
(diaz.)
+ 3-amido
4-cresol
6-sulfo-
acid
(diaz.)
+
orangeBrown
orange
4-kresol-
5-sulfo-
säure
(diaz.)
+ 3-amido
4-cresol
5-sulfo-
acid
(diaz.)
+
2-kresol-
5-sulfo-
säure
(diaz.)
+ 3-amido
2-cresol
5-sulfo-
acid
(diaz.)
+
4-kresol-
6-sulfo-
säure
(diaz.)
+ 3-amido
4-cresol
6-sulfo-
acid
(diaz.)
+
orangeBrown
orange
4-kresol-
5-sulfo-
säure
(diaz.)
+ 3-amido
4-cresol
5-sulfo-
acid
(diaz.)
+
2-kresol-
5-sulfo-
. säure
(diaz.)
+ 3-amido
2-cresol
5-sulfo-
. acid
(diaz.)
+
4-kresol-
6-sulfo-
säure
(diaz.)
+ 3-amido
4-cresol
6-sulfo-
acid
(diaz.)
+
braunreddish
Brown
orangereddish
orange
des festen FarbstoffesAppearance
of the solid dye
gelbbrownish
yellow
carbonsäurei-phenyl-5-pyrazolone-3-
carboxylic acid
p-sulfosäurei-phenyl-5-pyrazolone-
p-sulfonic acid
gelbbrownish
yellow
3-carbonsäurei-PhenyI-5-pyrazolone-p-sulfo-
3-carboxylic acid
gelbbrownish
yellow
in WasserColor of the solution
in water
gelbbrownish
yellow
gelbbrownish
yellow
braunreddish
Brown
braunreddish
Brown
Zusatz von AmmoniakColor of the solution
Addition of ammonia
orangered
orange
gelbbrownish
yellow
gelbgreenish
yellow
gelbbrownish
yellow
i gelbbrownish
i yellow
braunreddish
Brown
in cone. SchwefelsäureColor of the solution
in cone. sulfuric acid
verändertU.N
changes
farbiger
flockiger
Nieder
schlagorange
more colored
flaky
Low
blow
braundirty
Brown
Lösungyellow
solution
farbige
Lösungorange
colored
solution
Lösungyellow
solution
Lösungyellow
solution
braundirty
Brown
Lösungyellow
solution
gelbe
Lösungbrownish
yellow
solution
gelbbrownish
yellow
gelbgreenish
yellow
gelbreddish
yellow
gelbreddish
yellow
gelbgreenish
yellow
gelbreddish
yellow
rothbrownish
red
gelbgreenish
yellow
gelbreddish '
yellow
auf WolleDirect coloring
on wool
gelber
flockiger
Nieder
schlagorange
yellower
flaky
Low
blow
braunreddish
Brown
rother
Nieder
schlagbrick-
rother
Low
blow
rothbrownish
red
Lösungyellow
solution
rothbrownish
red
gelbe
Lösungbrownish
yellow
solution
rothbrownish
red
auf WolleChromed color
on wool
gelbbrownish
yellow
rothbluish
red
rothbluish
red
rothbluish
red
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE134163C true DE134163C (en) |
Family
ID=402310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT134163D Active DE134163C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE134163C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE749256C (en) * | 1942-05-16 | 1945-01-03 | Process for the preparation of o-oxyazo dyes | |
| US5194841A (en) * | 1990-12-19 | 1993-03-16 | Abb Power T&D Company, Inc. | Support structure for wound transformer core |
-
0
- DE DENDAT134163D patent/DE134163C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE749256C (en) * | 1942-05-16 | 1945-01-03 | Process for the preparation of o-oxyazo dyes | |
| US5194841A (en) * | 1990-12-19 | 1993-03-16 | Abb Power T&D Company, Inc. | Support structure for wound transformer core |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE134163C (en) | ||
| DE1769398B2 (en) | Water-soluble phthalocyanine azo dyes and processes for their preparation and their use | |
| DE163645C (en) | ||
| DE169579C (en) | ||
| DE1644175A1 (en) | Azo dyes | |
| DE134164C (en) | ||
| US242707A (en) | James h | |
| DE165743C (en) | ||
| US1821290A (en) | Manufacture of disazo dyes | |
| DE187150C (en) | ||
| DE189936C (en) | ||
| DE56992C (en) | Process for the preparation of dyes by the action of primary amines on the condensation product of nitrosodialkylaniline with /? - naphthol sulfonic acid | |
| DE74775C (en) | Process for the preparation of simple and mixed disazo dyes of the congo group, which contain naphthylglycine as a component | |
| DE72343C (en) | Process for the preparation of rosindone sulfonic acids | |
| DE908132C (en) | Use of phthalocyanines as Kuepen dyes | |
| DE445403C (en) | Process for the preparation of azo dyes | |
| DE97714C (en) | ||
| DE124790C (en) | ||
| DE110711C (en) | ||
| DE169683C (en) | ||
| DE591628C (en) | Process for the production of azo dyes of the stilbene series | |
| DE175827C (en) | ||
| DE86450C (en) | ||
| DE213278C (en) | ||
| DE168123C (en) |