CH179958A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH179958A CH179958A CH179958DA CH179958A CH 179958 A CH179958 A CH 179958A CH 179958D A CH179958D A CH 179958DA CH 179958 A CH179958 A CH 179958A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- aminobenzene
- azo dye
- production
- new
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 229920002955 Art silk Polymers 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- RIYSFSQPHCAGLS-UHFFFAOYSA-N 2-amino-3,5-dinitrobenzonitrile Chemical compound NC1=C(C#N)C=C([N+]([O-])=O)C=C1[N+]([O-])=O RIYSFSQPHCAGLS-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000003381 stabilizer 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paper (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 177266. Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, dass man einen neuen Azofarbstoff erhält, wenn man diazotiertes 6-Cyan-2 . 4-dinitro-l-aminobenzol mit 2-Me thoxy-5-methyl-l-N-(oxäthyl-methoxyäthyl)- aminobenzol vereinigt. Der neue Farbstoff bildet, eventuell aus Alkohol umkristallisiert, in getrocknetem Zustande ein dunkles Pul ver, das sich in organischen Lösungsmitteln, wie zum Beispiel Essigester, Aceton, Alko hol, Äther mit blauer Farbe löst.
Durch ge eignete Zusätze in feine Verteilung gebracht, färbt der Farbstoff Acetatkunstseide in kräf tigen, blauen Tönen. <I>Beispiel:</I> 20,8 Teile 6-Cyan-2. 4-dinitro-l-amino- benzol werden unter intensivem Rühren in 100 Teile Schwefelsäure eingetragen, unter Vermeidung einer zu starken Temperatur erhöhung. Man rührt bis zur völligen Lösung. Die erhaltene Lösung wird auf etwa 0 ge kühlt und mit einer aus 7 Teilen Natrium nitrit und etwa 70 Teilen Schwefelsäure in bekannter Weise hergestellten Lösung von Nitrosylschwefelsäure vereinigt.
Die erhal tene Mischung, die man falls nötig zur voll ständigen Lösung und Durchdiazotierung der Base gegebenenfalls unter Zusatz von Stabi lisatoren einige Zeit auf etwa 40 erwärmt hat, wird darauf unter kräftigem Rühren in eine mit viel gemahlenem Eis versetzte Lö sung von 23,9 Teilen 2-Methoxy-5-methyl-l- N - (oxäthyl - methoxyäthyl) - aminobenzol in der nötigen Menge verdünnter Mineralsäure bei 0 eingetragen. Die Farbstoffbildung, die man noch durch Zusatz von Natrium acetat beschleunigen kann, ist in kurzer Zeit beendet.
Der Farbstoff wird filtriert und neutral gewaschen.
Additional patent to main patent No. 177266. Process for the production of a new azo dye. It has been found that a new azo dye is obtained if diazotized 6-cyano-2. 4-dinitro-1-aminobenzene combined with 2-methoxy-5-methyl-1-N- (oxethyl-methoxyethyl) - aminobenzene. The new dye, possibly recrystallized from alcohol, forms a dark powder when dry, which dissolves in organic solvents such as ethyl acetate, acetone, alcohol, ether with a blue color.
Finely dispersed with suitable additives, the dye acetate artificial silk dyes in strong, blue tones. <I> Example: </I> 20.8 parts 6-cyan-2. 4-dinitro-1-aminobenzene are introduced into 100 parts of sulfuric acid with vigorous stirring, avoiding an excessive increase in temperature. The mixture is stirred until it is completely dissolved. The resulting solution is cooled to about 0 ge and combined with a solution of nitrosylsulfuric acid prepared in a known manner from 7 parts of sodium nitrite and about 70 parts of sulfuric acid.
The obtained mixture, which has been warmed to about 40 for some time if necessary for complete solution and thorough diazotization of the base, optionally with the addition of stabilizers, is then mixed with a lot of ground ice in a solution of 23.9 parts with vigorous stirring 2-Methoxy-5-methyl-1- N - (oxäthyl - methoxyethyl) - aminobenzene entered in the necessary amount of dilute mineral acid at 0. The dye formation, which can be accelerated by adding sodium acetate, is over in a short time.
The dye is filtered and washed neutral.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH179958T | 1934-02-23 | ||
| CH177266T | 1935-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH179958A true CH179958A (en) | 1935-09-30 |
Family
ID=25719941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH179958D CH179958A (en) | 1934-02-23 | 1934-02-23 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH179958A (en) |
-
1934
- 1934-02-23 CH CH179958D patent/CH179958A/en unknown
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