CH203870A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH203870A CH203870A CH203870DA CH203870A CH 203870 A CH203870 A CH 203870A CH 203870D A CH203870D A CH 203870DA CH 203870 A CH203870 A CH 203870A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- disazo dye
- preparation
- diazotized
- sulfonic acid
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 15
- 239000012670 alkaline solution Substances 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. <B>199787.</B> Verfahren zur Darstellung ein'es Disazofarbstoffes. Es wurde gefunden"dass man einen neuen, wertvollen Disazofarbstoff der Formel
EMI0001.0007
erhäJt, wenn man den durch Kuppeln von diazotierter 4-Nitro-l-aminobenzol-2-sulfon- säure mit 2,-Amino-8-n-aphthol-6-sulfonsäure in saurer Lösung erhältlichen Monoazofarb- stoff reduziert,
diazotiert, alkalisch mit Phenol vereinigt und den Disa-zofarbstoff in alkalischer Lösung mit p-Toluolsulfons5,ure- chlorid in der phenolisehen Hydroxylgruppe verestert.
Der neue Farbstoff, ein dunkles Pulver, löst sich in Wasser violett, in co-ne. Schwefel- sjä,ure blau und färbt Wülle und Seide in liellkchten violetten Tönen.
<I>Beispiel:</I> <B>21,8</B> Teile 4-Nitro-I#-aminobenizol-2;-sul- fons,ä,ure werdendiazotiert und mit 24 Teilen 2-Ami,n,o.8-na,phthol--6-sulfonsä,ure in saurer Lösung bei<B>0 1 C</B> gekuppelt. Nao,11 vollendeter Kombination erwähnt man auf 45-50'<B>C</B> und reduziert die Nitrogruppe mit<B>19,1</B> Teilen Nalriumsulfid während<B>3</B> Stunden, versetzt <B>mit</B> Salzsäure bis zur stark kongosauren Reaktion und filtriert.
Der gebildete Moneazofarbstoff wird mit Hilfe von Soda neutral #gelöst, filtriert, mit SalZSäUre versezt, mmt Nitrit weiter diazotiert und-. mit ein-er alkalischen Lösung von 9,4 Teil-en Plienol gekuppelt. Alsdann erwärmt man auf GO <B>' C,</B> versetzt mit Koehsal#z bis zur voll6tä.n#dig-en. Ausscheidung und filtriert.
Den so erhalteibeen, alikaliunechten Disazofarb- stoff unterwirft man in sodaalkalischer Lö sung bei 7-5 <B>' C</B> der Verersterung mit 40-50 Teilen p-Toluolsulion#säurechlerid bis zu er zielter Alkalieehtheit. Der ausgesalzene Farb stoff wird filtriert und getroeknet.
2D Er bildet ein dunkles Pulver, das sich in Wasser mit violetter, in cone. Schwefelsäure mit blau-er Farbe lbst und Wolle und Seide in lielltechten violetten Tönen anfärbt.
Additional patent to main patent no. <B> 199787. </B> Process for the preparation of a disazo dye. It has been found "that you have a new, valuable disazo dye of the formula
EMI0001.0007
obtained when the monoazo dye obtainable in acidic solution by coupling diazotized 4-nitro-1-aminobenzene-2-sulfonic acid with 2, -amino-8-n-aphthol-6-sulfonic acid is reduced,
diazotized, alkaline combined with phenol and the disazo dye esterified in alkaline solution with p-toluenesulfone5, acid chloride in the phenol hydroxyl group.
The new dye, a dark powder, dissolves violet in water, in co-ne. Sulfur sjä, ure blue, and dyes bulge and silk in light purple tones.
<I> Example: </I> <B> 21.8 </B> parts of 4-nitro-I # -aminobenizol-2; -sulfons, ä, ure are diazotized and with 24 parts of 2-ami, n, o.8-na, phthol - 6-sulfonic acid coupled in acidic solution at <B> 0 1 C </B>. Nao, 11 of the perfect combination is mentioned to 45-50 '<B> C </B> and reduces the nitro group with <B> 19.1 </B> parts of sodium sulfide for <B> 3 </B> hours, added < B> with </B> hydrochloric acid until a strong Congo acidic reaction and filtered.
The moneazo dye formed is dissolved neutrally with the help of soda, filtered, mixed with hydrochloric acid, and nitrite is further diazotized. coupled with an alkaline solution of 9.4 parts of plienol. Then warm up to GO <B> 'C, </B> mixed with Koehsal # z until completely dig-en. Excretion and filtered.
The alikaliunfast disazo dye obtained in this way is subjected to esterification with 40-50 parts of p-toluenesulionic acid chloride in a soda-alkaline solution at 7-5 C until alkalinity is achieved. The salted out dye is filtered and dried.
2D It forms a dark powder that turns violet in water, in cone. Sulfuric acid with a bluish color dyes itself and wool and silk in light purple tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH203870T | 1937-05-19 | ||
| CH199787T | 1938-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH203870A true CH203870A (en) | 1939-03-31 |
Family
ID=25723361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH203870D CH203870A (en) | 1937-05-19 | 1937-05-19 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH203870A (en) |
-
1937
- 1937-05-19 CH CH203870D patent/CH203870A/en unknown
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