DE126801C - - Google Patents
Info
- Publication number
- DE126801C DE126801C DENDAT126801D DE126801DA DE126801C DE 126801 C DE126801 C DE 126801C DE NDAT126801 D DENDAT126801 D DE NDAT126801D DE 126801D A DE126801D A DE 126801DA DE 126801 C DE126801 C DE 126801C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- moles
- mol
- dye
- cotton
- 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
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000000987 azo dye Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000001808 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000000975 dye Substances 0.000 description 11
- 229920000742 Cotton Polymers 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- NULAJYZBOLVQPQ-UHFFFAOYSA-N N-(1-Naphthyl)ethylenediamine Chemical compound C1=CC=C2C(NCCN)=CC=CC2=C1 NULAJYZBOLVQPQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-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
- 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)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
te 126801 KLASSE 22 a. te 126801 CLASS 22 a.
Wie in den Patentschriften 122904 und 126133 gezeigt worden ist, werden bisher unbekannte, ungeheizte Baumwolle direct färbende Azofarbstoffe durch Einwirkung von Diazoverbindungen auf freie Hydroxylgruppen enthaltende Harnstoffe bezw. Thioharnstoffe der Naphtalinreihe erhalten.As has been shown in patents 122904 and 126133, previously unknown, unheated cotton direct coloring azo dyes through the action of diazo compounds on ureas containing free hydroxyl groups respectively. Obtain thioureas of the naphthalene series.
Es hat sich nun weiter ergeben, dafs man zu Azofarbstoffen von ganz ähnlichen Eigenschaften gelangt, wenn man an Stelle der genannten Harnstoffe bezw. Thioharnstoffe die ähnlich constituirte Dioxydinaphtyläthylendiamindisulfosäure, die durch Einwirkung von Aethylenhaloiden auf die 2-Amido-5-naphtol-7-sulfosäure entsteht, mit Diazoverbindungen zu Farbstoffen vereinigt. Die hieraus gebildeten Farbstoffe besitzen die werthvolle Eigenschaft, ungeheizte Baumwolle direct anzufärben, in hohem Mafse ; sie zeichnen sich ebenfalls durch relativ grofse Säureechtheit und schöne, klare Nuance aus.It has now been found that azo dyes with quite similar properties can be obtained if you replace the ureas mentioned BEZW. Thioureas die similarly constituted dioxydinaphthylethylenediamine disulfonic acid, which is produced by the action of Ethylene haloids on the 2-amido-5-naphthol-7-sulfonic acid is formed, with diazo compounds combined to form dyes. The dyes formed from this have the valuable property to dye unheated cotton directly, to a large extent; they are also characterized by relatively high acid fastness and a beautiful, clear shade.
Bei der Herstellung der Farbstoffe verfährt man in der Weise, dafs man 2 Mol. von Diazoverbindungen mit der Dioxydinaphtyläthylendiamindisulfosäure vereinigt; an Stelle der 2 Mol. einer Monodiazoverbindung kann selbstverständlich auch 1 Mol. einer Tetrazoverbindung Verwendung finden.In the preparation of the dyes one proceeds in such a way that 2 moles of Diazo compounds combined with dioxydinaphthylethylenediaminedisulfonic acid; instead of of the 2 moles of a monodiazo compound can of course also 1 mole of a tetrazo compound Find use.
In eine sodaalkalische Lösung von 50,4 kg Dioxydinaphtyläthylendiamindisulfosäure läfst man unter gutem Rühren eine in üblicher Weise aus 21,4 kg p-Toluidin hergestellte Diazolösung zufliefsen. Nach mehrstündigem Rühren ist die Farbstoffbildung beendet. Es wird nun angewärmt, ausgesalzen, geprefst und getrocknet. Der Farbstoff färbt ungeheizte Baumwolle in schwach alkalischem Bade scharlachroth. In a soda-alkaline solution of 50.4 kg Dioxydinaphtyläthylendiamindisulfonic acid runs one prepared in the usual way from 21.4 kg of p-toluidine with thorough stirring Flow in diazo solution. After several hours of stirring, the formation of the dye has ended. It is now warmed up, salted out, pressed and dried. The dye stains unheated Cotton scarlet in a weakly alkaline bath.
30 kg p-Amidoacetanilid werden in üblicher Weise diazotirt und in eine mit überschüssiger Soda versetzte Lösung von 50,4 kg Dioxydinaphtyläthylendiamindisulfosäure einfliefsen gelassen. Die Farbstoffbildung beginnt sofort und ist nach mehrstündigem Rühren beendet. Es wird angewärmt, der Farbstoff ausgesalzen, geprefst und getrocknet. Er färbt ungeheizte Baumwolle in klaren, blaustichig-rothen Tönen an.30 kg of p-amidoacetanilide are diazotized in the usual way and in one with excess Soda-added solution of 50.4 kg of dioxydinaphthylethylenediaminedisulphonic acid flow in calmly. The formation of the dye begins immediately and ends after stirring for several hours. It is warmed up, the dye is salted out, pressed and dried. He dyes unheated ones Cotton in clear, bluish-red tones.
Eine in üblicher Weise aus 18,4 kg Benzidin hergestellte Tetrazodiphenylchloridlösung wird zu einer. mit überschüssiger Soda versetzten Lösung von 50,4 kg Dioxydinaphtylä'thylendiamindisulfosäure allmählich zugegeben. Nach mehrstündigem Rühren wird angewärmt, der gebildete Farbstoff ausgesalzen, geprefst und getrocknet. Er liefert auf ungeheizter Baumwolle ein klares Violett.One in the usual way from 18.4 kg of benzidine produced tetrazodiphenyl chloride solution becomes one. add excess soda Solution of 50.4 kg of dioxydinaphthylenediaminedisulfonic acid gradually admitted. After several hours of stirring, the mixture is warmed up, the dye formed is salted out and pressed and dried. On unheated cotton it produces a clear violet.
In analoger Weise verfährt man bei Benutzung anderer Diazoverbindungen bezw. Tetrazoverbindungen; an Stelle von 2 Mol. Monodiazoverbindung kann man auch 2 Mol.The procedure is analogous when using other diazo compounds BEZW. Tetrazo compounds; instead of 2 mol. Monodiazo compound, 2 mol.
einer Diazoazoverbindung oder eines Zwischenproductes aus einer Tetrazoverbindung und einem Amin, Phenol oder dergl. verwenden.a diazoazo compound or an intermediate of a tetrazo compound and an amine, phenol or the like. Use.
In folgender Tabelle sind die Nuancen einer Anzahl typischer Vertreter des vorliegenden Verfahrens angegeben.In the table below are the nuances of a number of typical representatives of the present one Procedure specified.
Farbstoff aus:Dye from:
2 Mol. p-Toluidin 2 moles of p-toluidine
2 Mol. p-Amidoacetanilid 2 moles of p-amidoacetanilide
2 Mol. a-Naphtylamin 2 moles of a-naphthylamine
2 Mol. ß-Naphtylamin ...: 2 mol. Ss-naphthylamine ...:
t Mol. Benzidin t moles of benzidine
2 Mol. des Zwischenproducts aus Benzidin und2 mol. Of the intermediate product from benzidine and
Salicylsäure Salicylic acid
2 Mol. des Zwischenproducts aus Benzin und2 moles of the intermediate product from gasoline and
i, 4-Naphtionsäure i, 4-naphthoic acid
2 Mol. Amidoazobenzol 2 moles of amidoazobenzene
färbt Baumwolle:colors cotton:
ι Mol. Dioxydi-ι Mol. Dioxydi-
naphtyläthylendiamindi-naphthylethylenediamine
sulfosäuresulfonic acid
scharlachroth blaustichig roth violettroth
blaustichig roth violettscarlet bluish red violet-red
bluish red violet
bordeauxbordeaux
bordeaux
blauroth.bordeaux
bluish red.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE126801C true DE126801C (en) |
Family
ID=395434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT126801D Active DE126801C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE126801C (en) |
-
0
- DE DENDAT126801D patent/DE126801C/de active Active
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