DE217627C - - Google Patents
Info
- Publication number
- DE217627C DE217627C DENDAT217627D DE217627DA DE217627C DE 217627 C DE217627 C DE 217627C DE NDAT217627 D DENDAT217627 D DE NDAT217627D DE 217627D A DE217627D A DE 217627DA DE 217627 C DE217627 C DE 217627C
- Authority
- DE
- Germany
- Prior art keywords
- ether
- aminophenyl
- amino
- disulfonic acid
- blue
- 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 9
- GOJFAKBEASOYNM-UHFFFAOYSA-N 2-(2-aminophenoxy)aniline Chemical class NC1=CC=CC=C1OC1=CC=CC=C1N GOJFAKBEASOYNM-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000008049 diazo compounds Chemical class 0.000 claims description 5
- 210000002268 Wool Anatomy 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- -1 o-aminophenyl-p-tolyl- ether Chemical compound 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 230000002378 acidificating Effects 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4,4'-Oxydianiline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims 3
- JMGOORYWTOXUQE-XOBOFAKPSA-N (6Z)-4-amino-3-[(4-nitrophenyl)diazenyl]-5-oxo-6-(phenylhydrazinylidene)naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=2C=C(S(O)(=O)=O)\C(=N/NC=3C=CC=CC=3)C(=O)C=2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 JMGOORYWTOXUQE-XOBOFAKPSA-N 0.000 claims 2
- JHZUBBUDGWYCTG-UHFFFAOYSA-N 2-(2-amino-4-chlorophenoxy)-5-chloroaniline Chemical compound NC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1N JHZUBBUDGWYCTG-UHFFFAOYSA-N 0.000 claims 2
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 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
- 238000004090 dissolution Methods 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/08—Disazo dyes in which the coupling component is a hydroxy-amino compound
- C09B33/10—Disazo dyes in which the coupling component is a hydroxy-amino compound in which the coupling component is an amino naphthol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE'22 α. GRUPPECLASS'22 α. GROUP
, Zusatz zum Patente 214496 vom 30. Mai 1908.*), Addition to patent 214496 of May 30, 1908. *)
Patentiert im Deutschen Reiche vom 24. Oktober 1908 ab. Patented in the German Empire on October 24, 1908 .
4 . ■ 4th ■
Gegenstand des Hauptpatents 214496 ist ein Verfahren zur Darstellung von sauren Wollfarbstoffen, welches darin besteht, daß man peri-Aminonaphtolsulfosäuren in beliebiger Reihenfolge mit ι Molekül der Diazoverbindungen von Aminophenyläthern oder ihrer Homologen und ι Molekül einer beliebigen anderen Diazoverbindung kuppelt.The subject of the main patent 214496 is a process for the preparation of acidic wool dyes, which consists in using peri-aminonaphthol sulfonic acids in any order with ι molecule of the diazo compounds of aminophenyl ethers or their homologues and ι molecule of any other diazo compound couples.
Es wurde nun gefunden, daß man zu Farbstoffen gelangt, welche dieselben wertvollen Färbeeigenschaften besitzen, wenn man die peri-Aminonaphtolsulfosäureri mit' 2 Molekülen der Diazoverbindung desselben oder verschiedener Aminophenyläther oder ihrer Homologen oder Substitutionsprodukte kuppelt.It has now been found that dyes are obtained which are valuable Have coloring properties if you use the peri-Aminonaphtolsulfosäureri with '2 molecules the diazo compound of the same or different aminophenyl ethers or their homologues or substitution products.
Es war nicht vorauszusehen, daß diese Farbstoffe noch genügend Löslichkeit besitzen würden, um in derselben Weise wie diejenigen des Hauptpatents zur Verwendung gelangen zu können. Man mußte vielmehr befürchten, daß man nach diesem Verfahren nur unlösliche bzw. sehr schwer lösliche Produkte erhalten würde.It was not foreseeable that these dyes would still have sufficient solubility in order to be able to use them in the same way as those of the main patent. Rather, one had to fear that only insoluble or very sparingly soluble products are obtained by this process would.
11,1 kg p-Aminophenylätherchlorhydrat werden in 12 kg roher Salzsäure und 120 1 Wasser fein verteilt und mit 3,5 kg Nitrit bei etwa 10 bis 20° diazotiert. Die Diazolösung wird zu einer kalten wäßrigen Auflösung von 15,9 kg ι · 8 · 4 · 6-Aminonaphtoldisulfosäure gegeben und etwa 10 Stunden bei gewöhnlicher Temperatur durchgerührt. Dann werden nochmals n,ι kg diazotiertes p-Aminophenylätherchlorhydrat zugegeben und unter Zusatz von Eis allmählich mit Soda alkalisch gemacht. Der ausgeschiedene Farbstoff wird abfiltriert, mit etwas sodahaltigem Wasser gewaschen und getrocknet. Er färbt Wolle in saurem Bade blauschwarz.11.1 kg of p-aminophenyl ether chlorohydrate will be finely divided in 12 kg of raw hydrochloric acid and 120 l of water and with 3.5 kg of nitrite at about 10 to 20 ° diazotized. The diazo solution becomes a cold aqueous dissolution of 15.9 kg ι · 8 · 4 · 6-aminonaphthol disulfonic acid given and stirred for about 10 hours at ordinary temperature. Then be again n, ι kg of diazotized p-aminophenyl ether chlorohydrate added and gradually made alkaline with soda with the addition of ice. The precipitated dye is filtered off, with washed a little soda water and dried. He dyes wool in an acid bath blue black.
Ersetzt man in dem obigen Beispiel beide Male oder bei der ersten oder zweiten Kupplung den ρ - Aminodiphenyläther durch beliebige andere Aminophenyläther oder ihre Homologe oder Substitutionsprodukte, so erhält man Farbstoffe von ähnlichen Eigenschaften.Replace both times in the above example or on the first or second coupling the ρ - aminodiphenyl ether by any other aminophenyl ethers or their homologues or substitution products, dyes with similar properties are obtained.
In der umstehenden Tabelle sind die Nuancen einiger der neuen Farbstoffe angegeben.The table below shows the nuances of some of the new dyes.
Claims (1)
verbindung von-and the diazo
connection of
Färbt Wolle I.
Dyes wool
äthero-amino-p-chlorophenyl-
ether
äthero-aminophenyl-p-tolyl-
ether
3 ■ 6-disulfosäurei-amino-8-naphthol-
3 ■ 6-disulfonic acid
äthero-amino-p-chlorophenyl-;
ether
äthero-amino-p-chlorophenyl-
ether
3 · 6-disulfosäureι-amino-8-naphtol-
3 x 6-disulfonic acid
4 · 6-disulfosäureι - Amino-8-naphtol-
4 x 6-disulfonic acid
4 · 6-disulfosäureι -amino-8-naphtol-
4 x 6-disulfonic acid
4 · 6-disulfosäurei-amino-8-naphthol-
4 x 6-disulfonic acid
phenyläthero-aminophenyl-o, -chlor-
phenyl ether
4 · 6-disulfosäureι -amino- 8-naphtol-
4 x 6-disulfonic acid
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE217627C true DE217627C (en) |
Family
ID=478919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT217627D Active DE217627C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE217627C (en) |
-
0
- DE DENDAT217627D patent/DE217627C/de active Active
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