DE58160C - Process for the preparation of disazo dyes of azoxyaniline and its homologues - Google Patents
Process for the preparation of disazo dyes of azoxyaniline and its homologuesInfo
- Publication number
- DE58160C DE58160C DENDAT58160D DE58160DA DE58160C DE 58160 C DE58160 C DE 58160C DE NDAT58160 D DENDAT58160 D DE NDAT58160D DE 58160D A DE58160D A DE 58160DA DE 58160 C DE58160 C DE 58160C
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- toluidine
- bodies
- preparation
- azoxyaniline
- 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 - Lifetime
Links
- 239000000975 dye Substances 0.000 title claims description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title description 2
- DJGYNCWNFYWANE-UHFFFAOYSA-N (3-aminophenyl)-(3-aminophenyl)imino-oxidoazanium Chemical compound NC1=CC=CC(N=[N+]([O-])C=2C=C(N)C=CC=2)=C1 DJGYNCWNFYWANE-UHFFFAOYSA-N 0.000 title 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- 210000002268 Wool Anatomy 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-Nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 claims description 3
- GDIIPKWHAQGCJF-UHFFFAOYSA-N 4-Amino-2-nitrotoluene Chemical compound CC1=CC=C(N)C=C1[N+]([O-])=O GDIIPKWHAQGCJF-UHFFFAOYSA-N 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- HFCFJYRLBAANKN-UHFFFAOYSA-N 2-methyl-3-nitroaniline Chemical compound CC1=C(N)C=CC=C1[N+]([O-])=O HFCFJYRLBAANKN-UHFFFAOYSA-N 0.000 claims description 2
- -1 nitroazo Chemical group 0.000 claims 2
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 claims 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 230000023298 conjugation with cellular fusion Effects 0.000 claims 1
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- 238000004043 dyeing Methods 0.000 claims 1
- 230000013011 mating Effects 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims 1
- 230000021037 unidirectional conjugation Effects 0.000 claims 1
- 239000001043 yellow dye Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229910000423 chromium oxide Inorganic materials 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
- POCJOGNVFHPZNS-UWVGGRQHSA-N Nitramine Natural products O[C@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-UWVGGRQHSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N Indigo Blue Chemical compound N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-N sodium;2-hydroxybenzoic acid Chemical compound [Na+].OC(=O)C1=CC=CC=C1O ABBQHOQBGMUPJH-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
- C09B43/08—Preparation of azo dyes from other azo compounds by reduction
- C09B43/10—Preparation of azo dyes from other azo compounds by reduction with formation of a new azo or an azoxy bridge
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
, ϋ , ϋ
Den Gegenstand des vorliegenden Zusatz-Patentes ' bildet die Darstellung von gelben, mit Chromoxyd gebeizte Wolle licht- und seifenecht färbenden Farbstoffen durch Anwendung der im Haupt-Patente No. 56456 beschriebenen Reductionsmethode auf Azofarbstoffe, welche durch Paarung von diazotirten .Nitraminen mit Salicylsäure oder Kresotinsäuren entstehen.The subject of the present additional patent 'forms the representation of yellow, with Chromium oxide stained wool to dye light and soap fast by application in the main patent no. 56456 described reduction method on azo dyes, which by pairing diazotized nitramines with salicylic acid or cresotinic acids.
Beispiel I. Darstellung eines Azoxyfarbstoffes aus m-Nitranilin: .Example I. Preparation of an azoxy dye from m-nitroaniline:.
13,8 kg m-Nitranilin und 35,5 kg gewöhnliche Salzsäure werden mit 1 500 1 Wasser in Lösung gebracht und in die kalte Flüssigkeit 22,5 1 Natriumnitrit von 33 pCt. Reingehalt zugegossen. Nach erfolgter Reaction wird die Lösung des Diazokörpers mit 1000 1 salicylsaurem Natron, welche 13,8 kg reine Säure enthalten, gemischt und die Mischung sich selbst überlassen. Nach einigen Stunden werden 284 1 Natronlauge von 400B. und 16 kg Traubenzucker von 80 pCt. Reingehalt zugegeben. Nun wird die Flüssigkeit auf 40 bis 6o° C. erwärmt und so lange auf dieser Temperatur erhalten, bis eine herausgenommene Probe ungeheizte Wolle in saurem Bade nicht mehr anfärbt. Dieser Punkt wird in 4 bis 8 Stunden erreicht. Durch Ansäuren der Mischung mit Schwefel- oder Salzsäure wird der Farbstoff in unlöslicher Form gefällt. Er wird auf Filtern gesammelt, gewaschen, geprefst und mit 28 1 Natronlauge von 40° B. in wasserlösliches Natronsalz übergeführt, welches am besten in Form von Paste verbraucht wird.13.8 kg of m-nitroaniline and 35.5 kg of common hydrochloric acid are dissolved in 1,500 liters of water and 22.5 liters of 33 pCt sodium nitrite are added to the cold liquid. Poured in purity. After the reaction has taken place, the solution of the diazo body is mixed with 1000 liters of sodium salicylic acid, which contains 13.8 kg of pure acid, and the mixture is left to itself. After several hours, 284 1 of sodium hydroxide solution 40 0 B. and 16 kg of glucose by 80 are cent. Purity added. The liquid is now heated to 40 to 60 ° C. and kept at this temperature until a sample that has been removed no longer stains unheated wool in an acidic bath. This point is reached in 4 to 8 hours. Acidifying the mixture with sulfuric or hydrochloric acid precipitates the dye in insoluble form. It is collected on filters, washed, pressed and converted into water-soluble sodium salt with 28 l of 40 ° B. sodium hydroxide solution, which is best consumed in the form of paste.
Beispiel II. In Beispiel I wird das m-Nitranilin durch 15,2 kg m-Nitro-o-toluidin (Schmelzpunkt 107°) oder m-Nitro-p-toluidin (Schmelzpunkt 78°) oder durch die Mischung derselben ersetzt. Die Reduction wird so lange fortgesetzt, bis eine herausgenommene Probe nach Ausfärben auf mit Chromoxyd gebeizter Wolle die Abwesenheit des Nitrokörpers zu erkennen giebt.Example II. In Example I, the m-nitro-niline is replaced by 15.2 kg of m-nitro-o-toluidine (Melting point 107 °) or m-nitro-p-toluidine (Melting point 78 °) or replaced by the mixture thereof. The reduction will be like this continued for a long time until a sample was taken out after staining with chromium oxide stained wool reveals the absence of the nitro body.
Beispiel III. In Beispiel I und II wird die Salicylsäure durch 15,2 kg einer der Kresotinsäuren ersetzt und im übrigen wie in Beispiel I und II verfahren. Das Ende der Reduction wird durch Probefärben erkannt.Example III. In Examples I and II, the salicylic acid becomes one of the cresotinic acids with 15.2 kg replaced and otherwise proceed as in Examples I and II. The end of the reduction is recognized by test staining.
Der Azoxyfarbstoff theilt im allgemeinen der gebeizten Wolle eine grünlichere Nuance mit als der entsprechende nitrirte Azokörper.The azoxy dye generally gives the stained wool a greener shade than the corresponding nitrided azo body.
Alle diese Farbstoffe, die von einander wenig verschieden sind, besitzen die Eigenschaft, mit Chromoxyd gebeizte Wolle licht- und seifenecht gelb zu färben. Die Echtheit dieser Farben steht weder dem Indigoblau, noch dem Alizarinroth nach.All of these dyes, which are little different from one another, have the property of having To dye chromium oxide stained wool yellow, lightfast and soapfast. The authenticity of these colors is neither inferior to the indigo blue nor the alizarin red.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE58160C true DE58160C (en) |
Family
ID=332485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT58160D Expired - Lifetime DE58160C (en) | Process for the preparation of disazo dyes of azoxyaniline and its homologues |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE58160C (en) |
-
0
- DE DENDAT58160D patent/DE58160C/en not_active Expired - Lifetime
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