DE82233C - - Google Patents
Info
- Publication number
- DE82233C DE82233C DENDAT82233D DE82233DA DE82233C DE 82233 C DE82233 C DE 82233C DE NDAT82233 D DENDAT82233 D DE NDAT82233D DE 82233D A DE82233D A DE 82233DA DE 82233 C DE82233 C DE 82233C
- Authority
- DE
- Germany
- Prior art keywords
- amidocresol
- dye
- hydrochloric acid
- liters
- soda
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- LGDPTPLJZGPOJL-UHFFFAOYSA-N N,N-dimethyl-2-nitrosoaniline Chemical compound CN(C)C1=CC=CC=C1N=O LGDPTPLJZGPOJL-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- -1 naphthoquinone dichlorimide Chemical compound 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- SNZJKSOQFORKLF-UHFFFAOYSA-N 4-methylcyclohexa-1,5-diene-1,4-diamine;hydrochloride Chemical compound Cl.CC1(N)CC=C(N)C=C1 SNZJKSOQFORKLF-UHFFFAOYSA-N 0.000 description 1
- FOUKKZFWDLRHDK-UHFFFAOYSA-N Cl.N(=O)C1=C(N(CC)CC)C=CC=C1 Chemical compound Cl.N(=O)C1=C(N(CC)CC)C=CC=C1 FOUKKZFWDLRHDK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- NPZDNLCYFLDJFA-UHFFFAOYSA-N N,N-dimethyl-2-nitroaniline Chemical compound CN(C)C1=CC=CC=C1[N+]([O-])=O NPZDNLCYFLDJFA-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-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
- C09B19/00—Oxazine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Im weiteren Verlauf der Untersuchungen über die Bildung von Oxazinen aus Derivaten des m-Amidophenols hat sich herausgestellt, dafs auch das unsubstituirte m-Amidokresol (CiZ3 : NH.2 : OH= 1:2:4) zum Unterschied von seinem niederen Homologen (vgl. Patentschrift Nr. 55059) in sehr werthvolle grün- bis rothblaue Farbstoffe übergeführt werden kann.In the course of studies on the formation of oxazines from derivatives of m-amidophenol has turned out, that also the unsubstituirte m-Amidokresol (ClZ 3: NH 2. OH = 1: 2: 4) to distinguish it from its lower homologues ( see patent specification no. 55059) can be converted into very valuable green to red-blue dyes.
Die totale Verschiedenheit der vorliegenden Amidokresolfarbstoffe von den entsprechenden Amidophenolderivaten zeigt sich durch nachstehende Vergleichung des Farbstoffs aus Nitrodimethylanilin mit dem entsprechenden Farbstoff der Patentschrift Nr. 55059.The total difference between the present amidocresol dyes and the corresponding ones Amidophenol derivatives are shown by the following comparison of the dye from nitrodimethylaniline with the corresponding dye of patent specification No. 55059.
Farbstoff ausDye off
AussehenAppearance
löst" sich in concentrirter Schwefelsäure dissolves in concentrated sulfuric acid
beim Verdünnen mit Wasser aus der
wässerigenwhen diluting with water from the
water
Lösung
fällt Laugesolution
falls lye
Fällungprecipitation
in
Aetherin
Ether
FärbtColors
tannirtetannied
Baumwollecotton
Nitrosodimethylanilin
+ m - AmidophenolNitrosodimethylaniline
+ m - amidophenol
schwarzesblack
amorphesamorphous
Pulverpowder
schwarzbraun black-brown
röthlichschwarze Lösung schwärzlichen
Niederschlagreddish black solution blackish
Precipitation
kaum löslichhardly soluble
grauGray
Nitrosodimethylanilin
+ m-AmidokresolNitrosodimethylaniline
+ m-amidocresol
grün-green-
länzendesshining
rystallini-rystallini-
sches Pulvernice powder
grüngreen
blaue Lösung rothbraunen
Niederschlagblue solution reddish brown
Precipitation
gelbrothyellow-red
löslich mitsoluble with
gelblichermore yellowish
FluorescenzFluorescence
schön
grünblau.Nice
green Blue.
Die Ueberführung geschieht nach den im Haupt-Patent und seinen Zusätzen geschilderten Methoden, also zunächst durch Einwirkung von ρ - Nitrosoderivaten aromatischer Amine oder von Dichlorimiden, ferner durch Zusammenoxydiren mit aromatischen p-Diaminen, oder endlich durch Erhitzen mit Azofarbstoffen, welche bei der Reduction p-Diamine liefern.The transfer takes place according to the described in the main patent and its additions Methods, i.e. initially through the action of ρ - nitroso derivatives of aromatic amines or of dichlorimides, also by oxidizing together with aromatic p-diamines, or, finally, by heating with azo dyes, which in the reduction are p-diamines deliver.
ι. 2,5 kg salzsaures Nitrosodiäthylanilin werden mit ι kg m-Amidokresol und 5 1 Spiritus vorsichtig und unter Vermeidung einer zu heftigen Reaction unter Rückflufs erwärmt. Nach Beendigung der Farbstoffbildung wird mit 50 1 heilsem Wasser verdünnt; Verunreinigungen werden durch Zusatz von etwa 0,4 kg Soda entfernt und der Farbstoff aus demι. 2.5 kg of hydrochloric acid nitrosodiethylaniline will be with ι kg m-amidocresol and 5 1 alcohol carefully and avoiding a to violent reaction heated under reflux. After the dye formation is complete diluted with 50 liters of healthy water; Impurities are removed by adding about 0.4 kg Soda removed and the dye out of the
Filtrat durch Kochsalz und Chlorzink und etwas Salzsäure gefällt.The filtrate is precipitated with table salt and zinc chloride and a little hydrochloric acid.
2. 8 kg Naphtochinondichlorimid werden mit 4 kg m-Amidokresol und 50 1 Methylalkohol unter Rückflufs bis zur völligen Lösung und Aufhören der Reaction erwärmt. Man verdünnt mit heifsem Wasser, reinigt mit Natriumacetat und fällt den Farbstoff zweckmäfsig als Chlorzinkdoppelsalz.2. 8 kg of naphthoquinone dichlorimide are mixed with 4 kg of m-amidocresol and 50 l of methyl alcohol heated under reflux until complete dissolution and cessation of the reaction. Man diluted with hot water, cleaned with sodium acetate, and expediently precipitated the dye as chlorine zinc double salt.
3. 6 kg m-Amidokresol werden mit 20 kg salzsaurem Benzolazodimethylanilin, 301 Spiritus und 5 1 Salzsäure (3oproc.) unter Rückflufs längere Zeit erwärmt, bis die ursprünglich rothe Lösung blau geworden und der Azokörper verschwunden ist. Man verdünnt mit heifsem Wasser, reinigt mit etwa 5 kg Soda und fällt aus dem Filtrat den Farbstoff aus.3. 6 kg of m-amidocresol are mixed with 20 kg of hydrochloric acid benzolazodimethylaniline, 301 alcohol and 5 1 hydrochloric acid (3oproc.) heated under reflux for a long time until the originally The red solution has turned blue and the azo body has disappeared. Dilute with hot water and clean with about 5 kg of soda and the dye precipitates from the filtrate.
4. 6 kg m-Amidokresol, 10 kg salzsaures p-Toluylendiamin und 20 kg essigsaures Natron werden in 500 1 Wasser heifs gelöst und durch allmählichen Zusatz von ungefähr 140 1 Eisenchloridlösung von 15 pCt. oxydirt. Nach dem Erkalten wird filtrirt und der Farbstoff aus dem Filtrat als Chlorzinkdoppelsalz gefällt.4. 6 kg of m-amidocresol, 10 kg of hydrochloric acid p-toluenediamine and 20 kg of acetic acid soda are dissolved in 500 liters of hot water and by gradually adding about 140 liters of ferric chloride solution from 15 pCt. oxidized. After cooling, it is filtered and the dye is removed the filtrate is precipitated as zinc chloride double salt.
5. 3,6 kg m-Amidokresol werden mit 10 kg5. 3.6 kg of m-amidocresol are used with 10 kg
salzsaurem Amidoazotoluol (aus o-Toluidin), 5 1 Salzsäure (30 proc.) und 7,5 1 Glycerin bei 120 bis 1400 C. gelinde bis zur Beendigung der Reaction und ruhigem FfWsen ileTScnTnelze erhitzt. Man verdünnt hierauf mit 150 1 Wasser, reinigt mit 1,5 kg Soda, filtrirt, kocht den Filterrückstand nochmals aus und fällt die vereinigten Filtrate mit Kochsalz und Chlorzink. Der so erhaltene Farbstoff ist identisch -mit dem nach Beispiel 4. erhaltenen. ^(proc. 30) Amidoazotoluol hydrochloric acid (from o-toluidine), 5 1 7.5 1 hydrochloric acid and glycerol at 120 to 140 0 C. gently heated until completion of the reaction, and calm FfWsen ileTScnTnelze. It is then diluted with 150 liters of water, purified with 1.5 kg of soda, filtered, the filter residue is boiled again and the combined filtrates are precipitated with common salt and zinc chloride. The dye obtained in this way is identical to that obtained in Example 4. ^
Claims (3)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE82233C true DE82233C (en) |
Family
ID=354651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT82233D Active DE82233C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE82233C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0047429A1 (en) * | 1980-09-05 | 1982-03-17 | BASF Aktiengesellschaft | Basic oxazine dyestuffs |
-
0
- DE DENDAT82233D patent/DE82233C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0047429A1 (en) * | 1980-09-05 | 1982-03-17 | BASF Aktiengesellschaft | Basic oxazine dyestuffs |
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