DE61053C - Process for the preparation of disazo dyes from diamidodiphenoxyacetic acid - Google Patents
Process for the preparation of disazo dyes from diamidodiphenoxyacetic acidInfo
- Publication number
- DE61053C DE61053C DENDAT61053D DE61053DA DE61053C DE 61053 C DE61053 C DE 61053C DE NDAT61053 D DENDAT61053 D DE NDAT61053D DE 61053D A DE61053D A DE 61053DA DE 61053 C DE61053 C DE 61053C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- diamidodiphenoxyacetic
- preparation
- disazo dyes
- 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.)
- 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
- 239000002253 acid Substances 0.000 title description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241000874887 Pseudophilotes bavius Species 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000980 acid dye Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000000725 suspension 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
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
Die nach den Angaben der Patentschrift No. 55506 in Form ihrer Alkalisalze dargestellte Diamidodiphenoxylessigsäure besitzt die Eigenschaft, durch Diazotiren und Combiniren mit Aminen, Phenolen und deren Sulfo- und Carbonsäuren substantive Disazofarbstoffe zu liefern, welche dem seither noch unbekannten Typus:According to the information in patent no. 55506 in the form of their alkali salts Diamidodiphenoxyacetic acid has the property of being diazotized and combined with amines, phenols and their sulfo and carboxylic acids substantive disazo dyes deliver which of the since then still unknown type:
ch/°~ch / ° ~
N=N-X .N=N-XN = N-X. N = N-X
. H. H
0-CHn 0-CH n
CO2HCO 2 H
entsprechen und somit in ihrer Zusammensetzung einerseits an Dianisidin-, andererseits an Diamidodiphensäurefarbstoffe erinnern.and thus in their composition on the one hand to dianisidine, on the other hand remind of diamidodiphenic acid dyes.
Unter diesen Combinationen sind manche durch die Schönheit und Klarheit ihrer Ausfärbungen ausgezeichnet, und es können damit z. B. blaue Farbentöne von bisher nicht erreichter schoner grüner Nuance erzielt werden. Aufserdem besitzen die Färbungen zum Theil die merkwürdige Eigenschaft, unter Einwirkung von Kupfersalzen etc. nicht nur an Licht- und Waschechtheit erheblich zu gewinnen, sondern auch in ganz andersartige Farbentöne überzugehen, z. B. Blau in Grün, Roth in Blau.Among these combinations are some for the beauty and clarity of their coloring excellent, and it can be used, for. B. blue hues of previously unachievable beautiful green shade can be achieved. In addition, some of the colorations have the strange property, under the action of copper salts etc. not only in light and To significantly improve washfastness, but also to transition into completely different shades of color, z. B. blue in green, red in blue.
Als besonders werthvoll haben sich bis jetzt die Combinationen mit folgenden Componenten erwiesen:So far, the combinations with the following components have proven to be particularly valuable proven:
Farbecolour
durch
Kupfervitriolby
Blue vitriol
Mit 2 MolecUlen 1 · 5-Naphtolsulfosäure With 2 molecules of 1 · 5-naphthol sulfonic acid
2 - ι · 8-Benzoylamidonaphtolsulfosäure2 - ι · 8-Benzoylamidonaphtholsulfonic acid
2 - ι · 8-Dioxynaphtalin 2 - ι · 8-Dioxynaphthalene
- 2 - 2 · 6-Dioxynaphtalin - 2-2 x 6-dioxynaphthalene
- 2 - ß-Naphtylamin-β-sulfosäure (Brön- 2 - ß-naphthylamine-β-sulfonic acid (Brön
ner) ner)
- 2 - ß-Naphtylamin - 2 - ß-naphthylamine
ι Molecül Salicylsäure undι Molecül salicylic acid and
ι - Chrysoidin ι - chrysoidine
violettblauviolet blue
grünblaugreen Blue
violettblauviolet blue
blaublue
bläuliches Roth
bläuliches Rothbluish red
bluish red
gelbbraunyellow-brown
grüngreen
grüngreen
mifsfarben
graugrünmifs
gray-green
blau
blaublue
blue
tiefdunkelbraundeep dark brown
Die Darstellung dieser Farbstoffe vollzieht sich unter ganz ähnlichen Bedingungen wie diejenige der Dianisidin- oder Diamidodiphensäurefarbstoffe. The representation of these dyes takes place under very similar conditions as that of the dianisidine or diamidodiphenic acid dyes.
Beispiel. Darstellung des Farbstoffes aus Diamidodiphenoxylessigsäure und 1 · 8-Dioxynaphtalin. Example. Representation of the dye from diamidodiphenoxyacetic acid and 1 · 8-dioxynaphthalene.
17,8 kg Natronsalz der Diamidodiphenoxylessigsäure werden in 300 1 Wasser unter Zusatz von 150 kg Eis und 30 1 concentrirter Salzsäure von 1,19 spec. Gew. gelöst. Man diazotirt in üblicher Weise durch Eingiefsen einer Lösung von 7 kg Natriumnitrit in 20 1 Wasser. Nach kurzem Stehen giefst man die17.8 kg of the sodium salt of diamidodiphenoxyacetic acid are dissolved in 300 liters of water with the addition of 150 kg of ice and 30 liters of concentrated hydrochloric acid of 1.19 spec. Weight dissolved. Man diazotized in the usual way by pouring a solution of 7 kg of sodium nitrite in 20 liters Water. After standing for a short time you pour it
erhaltene klare gelbliche Lösung der Tetrazoverbindung in eine Suspension von 18 kg ι · 8-Dioxynaphtalin, welche bereitet worden ist durch Auflösen desselben in 4000 1 Wasser unter Zusatz von 10 1 Natronlauge, 1000 kg Eis und 70 kg krystallisirtem Natriumacetat und darauf folgendes Versetzen mit Essigsäure bis zur schwach sauren Reaction. Nach 24 stündigem Rühren bezw. nach vollendeter Farbstoffbildung macht man die Flüssigkeit mit Soda alkalisch, kocht auf, salzt aus, preist und trocknet.obtained clear yellowish solution of the tetrazo compound in a suspension of 18 kg ι · 8-Dioxynaphthalene, which has been prepared by dissolving it in 4000 l of water with the addition of 10 l of sodium hydroxide solution, 1000 kg of ice and 70 kg of crystallized sodium acetate and then adding acetic acid until the reaction is weakly acidic. To 24 hours of stirring respectively. after the dye formation is complete, the liquid is made alkaline with soda, boil, salt out, praise and dry.
Zur Darstellung der entsprechenden Farbstoffcombinationen mit den anderen Farbstoffcomponenten gelten die gleichen Combinationsbedingungen, wie bei der Vereinigung mit anderen Tetrazoverbindungen; es werden also die Combinationen mit Aminen und Amido-, säuren in neutraler oder schwach essigsaurer, diejenigen mit Phenolen etc. in alkalischer Lösung vorgenommen.To show the corresponding dye combinations the same combination conditions apply to the other dye components, as with the union with other tetrazo compounds; so it will be the combinations with amines and amido acids in neutral or weakly acetic acid, those with phenols etc. made in alkaline solution.
Claims (4)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE61053C true DE61053C (en) |
Family
ID=335142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT61053D Expired - Lifetime DE61053C (en) | Process for the preparation of disazo dyes from diamidodiphenoxyacetic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE61053C (en) |
-
0
- DE DENDAT61053D patent/DE61053C/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE61053C (en) | Process for the preparation of disazo dyes from diamidodiphenoxyacetic acid | |
| DE80421C (en) | ||
| DE47301C (en) | Process for the preparation of tetrazo dyes from the ethylene ether of p-amidophenol | |
| DE86970C (en) | ||
| DE84991C (en) | ||
| DE89285C (en) | ||
| DE251479C (en) | ||
| DE143897C (en) | ||
| DE106721C (en) | ||
| DE167468C (en) | ||
| DE82572C (en) | ||
| DE281448C (en) | ||
| DE196924C (en) | ||
| DE155572C (en) | ||
| DE723845C (en) | Process for the preparation of a water-soluble monoazo dye | |
| DE229525C (en) | ||
| DE591549C (en) | Process for the production of water-insoluble azo dyes | |
| DE110711C (en) | ||
| DE101274C (en) | ||
| DE241678C (en) | ||
| DE171904C (en) | ||
| DE139287C (en) | ||
| DE497000C (en) | Process for the preparation of water-insoluble azo dyes | |
| DE150124C (en) | ||
| DE670432C (en) | Process for the preparation of disazo dyes |