CH191741A - Process for the preparation of a new polyazo dye. - Google Patents
Process for the preparation of a new polyazo dye.Info
- Publication number
- CH191741A CH191741A CH191741DA CH191741A CH 191741 A CH191741 A CH 191741A CH 191741D A CH191741D A CH 191741DA CH 191741 A CH191741 A CH 191741A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- molecule
- brown
- new
- acid
- Prior art date
Links
- -1 polyazo Polymers 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 150000008049 diazo compounds Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 4
- PXUQTDZNOHRWLI-QOPOCTTISA-O Primulin Natural products O(C)c1c(O)c(OC)cc(-c2c(O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O3)cc3c(O)cc(O)cc3[o+]2)c1 PXUQTDZNOHRWLI-QOPOCTTISA-O 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 3
- YDIKCZBMBPOGFT-PWUSVEHZSA-N Malvidin 3-galactoside Chemical compound [Cl-].COC1=C(O)C(OC)=CC(C=2C(=CC=3C(O)=CC(O)=CC=3[O+]=2)O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)=C1 YDIKCZBMBPOGFT-PWUSVEHZSA-N 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 238000006396 nitration reaction Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 9
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/50—Tetrazo dyes
- C09B35/58—Tetrazo dyes of the type
-
- 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
- C09B35/50—Tetrazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 189139. Verfahren zur Herstellung eines neuen Polyazofarbstoffes. Es wurde gefunden, dass man einen neuen Azofarbstoff erhält, wenn mann Resorcin, @di- azotiertes Primulin und den,diazotierten Dis- azofarbstoff,
der selbst entsteht durch Ver einigen von 1 Mal. tetrazotiertem 3,3'-Dime- thyl-4,4'-ddaminodliphenyl mit 1 Mol @Salicyl- säure und 1 Mol des technischen Gemisches der 1-Naphthylamin-,6- bezw. 7-:
sulfonsäure, erhalten durch Reduktion des Nitrierungspro- duktes der ss-Naphthalinsulfonsäure, aufein- and-er einwirken lässt, und zwar derart, dass man zuerst ein Molekül Resorcin mit einem Molekül einer der beiden Diazov erbindungen kuppelt, worauf man das :so erhaltene Kupp lungsprodukt mit einem Molekül,der zweiten Diazoverbindung vereinigt.
Der neue Farb stoff stellt ein schwarzbraunes Pulver dar, das sich in Wasser auf Sodazusatz ,mit brauner, in konzentrierter Schwefelsäure mit violetter Farbe löst. Er erzeugt auf Baum wolle braune Töne.
<I>Beispiel:</I> 21,2 Teile 3,3'-Dimethyl-4,4'-:diaminädi- phenyl werden in üblicher Weise tetrazotiert und mit 15 Teilen Salicylsäure in soloalka- lischer Lösung .gekuppelt.
Nach beendä@gter Kupplung wird eine Lösung eines Gemisches von 214,5 Teilen der Na-!Salze der 1-Amino- niaphthalin-6- bezw. 7-sulfons@äure zugegeben. Nach beendigter Kupplung wird der gebil- dete Farbstoff filtriert, mit Wasser ange rührt,
weiter mit Nitrit und Salzsäure diazo- tiert und mit dem Zwischenfarbstoff aus 5:-8,6 Teilen Primulin und 11 Teilen Resorcin, in soda.a@lkalischer Lösung vereinigt. Dieser Zwischenfarbstoff entsteht, wenn man 58;
6 Tale Primulin (sulfierte Primulinbase) di- azzotiert, die so erhaltene Diazolösung zu einer wässerigen Lösung von 11 Teilen Resorcin zugibt und die mit @d-er berech neten Menge Soda abstumpft;
sobald,die Di- azoverbindung verschwunden ist, wird der Farbstoff mit Kochsalz .gefällt, filtriert und mit Wasser wieder angerührt. Nach vollende ter Kupplung des Tetrakisazofarbstoffes wird der Farbstoff bei 60 bis<B>70'</B> Hausgesalzen, fil triert und getrocknet. Er stellt eindunkles Pulver dar, :das sieh in Wasser mit brauner Farbe, in konzentrierter Schwefelsäure und violetter Farbe löst. Die Färbung auf Baum wolle ist braun.
Additional patent to main patent No. 189139. Process for the production of a new polyazo dye. It has been found that a new azo dye is obtained when resorcinol, @ diazotized primulin and the diazotized disazo dye,
which itself is created by combining 1 time. tetrazotized 3,3'-dimethyl-4,4'-ddaminodliphenyl with 1 mol @ salicylic acid and 1 mol of the technical mixture of 1-naphthylamine, 6- and respectively. 7-:
Sulphonic acid, obtained by reducing the nitration product of β-naphthalenesulphonic acid, is allowed to act on one another, namely in such a way that first a molecule of resorcinol is coupled with a molecule of one of the two diazo compounds, whereupon the coupling product thus obtained is coupled combined with one molecule, the second diazo compound.
The new dye is a black-brown powder that dissolves in water with the addition of soda, with brown, in concentrated sulfuric acid with a purple color. It produces brown tones on cotton.
<I> Example: </I> 21.2 parts of 3,3'-dimethyl-4,4 '-: diaminadiphenyl are tetrazotized in the usual way and coupled with 15 parts of salicylic acid in a solo alkaline solution.
After the coupling has ended, a solution of a mixture of 214.5 parts of the sodium salts of 1-amino-niaphthalene-6- or. 7-sulfonic acid added. After the coupling is complete, the dyestuff formed is filtered off, stirred with water,
further diazotized with nitrite and hydrochloric acid and combined with the intermediate dye of 5: -8.6 parts of primulin and 11 parts of resorcinol in a soda-alkaline solution. This intermediate dye arises when one 58;
6 Tale primulin (sulfated primulin base) is diazo-doped, the diazo solution thus obtained is added to an aqueous solution of 11 parts of resorcinol and the amount of soda calculated with @ d-er is blunted;
as soon as the diazo compound has disappeared, the dye is precipitated with common salt, filtered and stirred up again with water. After coupling of the tetrakisazo dye is complete, the dye is filtered at 60 to 70 'house salts, and dried. It represents a dark powder: it dissolves in water with a brown color, in concentrated sulfuric acid and purple in color. The color on cotton is brown.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH469646X | 1936-01-09 | ||
| CH191741T | 1936-01-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH191741A true CH191741A (en) | 1937-06-30 |
Family
ID=25722169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH191741D CH191741A (en) | 1936-01-09 | 1936-01-09 | Process for the preparation of a new polyazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH191741A (en) |
-
1936
- 1936-01-09 CH CH191741D patent/CH191741A/en unknown
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