CH202163A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH202163A CH202163A CH202163DA CH202163A CH 202163 A CH202163 A CH 202163A CH 202163D A CH202163D A CH 202163DA CH 202163 A CH202163 A CH 202163A
- Authority
- CH
- Switzerland
- Prior art keywords
- disazo dye
- acid
- blue
- preparation
- disazo
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 claims description 3
- 210000004209 hair Anatomy 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- -1 toluenesulfonic acid ester Chemical class 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- FUXZRRZSHWQAAA-UHFFFAOYSA-N 5,5-dioxodibenzothiophene-3,7-diamine Chemical compound C1=C(N)C=C2S(=O)(=O)C3=CC(N)=CC=C3C2=C1 FUXZRRZSHWQAAA-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 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
- C09B35/34—Disazo dyes characterised by the tetrazo component the tetrazo component being heterocyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 194456. Gegenstand dieses Patentes ist ein Ver fahren zur Herstellung eines Disazofarbstoffes, welches dadurch gekennzeichnet ist, dass man die Tetrazoverbindung der Benzidinsulfon- disulfonsäure (Beilstein, IV. Aufl., Bd. XVHI, S.
636) mit 2 Molekülen des Toluolsulfon- säureesters der 2-Atnino-8-oxytraphtalitt-6- sulfonsäure kuppelt und aus dem erhaltenen Disazofarbstoff die Toluolsulfonsäurereste ab spaltet.
Der Disazofarbatoff kristallisiert in feinen, blauen Nädelchen, löst sich in Wasser mit reinblauer, in konzentrierter Schwefelsäure mit violettroter Farbe und ist identisch mit dem nach Zusatzpatent Nr. 199655 dargestell ten Produkt.
Beispiel; 40,6 g Benzidinsulfondisulfonsäure werden mit<B>13,8</B> g Natriumnitrit und 60 g konz. Salz säure in bekannter Weise tetrazotiert und die erhaltene Tetrazoverbindung wird bei Gegenwart von Natriumacetat mit 78,6 g des Toluolsulfonsäureesters der 2-Amirto-8-oxy- ttaphtalitt-6-sulfonsäure gekuppelt.
Der so er- haltene violette Disazofarbatoff wird abfil- triert, getrocknet und in die zehnfache Menge konz. Schwefelsäure eingerührt. Durch vor sichtigen Zusatz von Wasser steigert man dann die Temperatur auf 75-80 , wobei der Farbstoff unter Abspaltung der Toluolsulfon- säurereste in Lösung geht. Nach beendeter Verseifung giesst man die schwefelsaure Lö sung in eine Mischung von Wasser und Eis und isoliert den ausgeschiedenen Disazofarb- atoff.
Der Disazofarbstoff kristallisiert in feinen blauen Nädelchen, löst sich in Wasser mit reinblauer, in konzentrierter Schwefelsäure mit violettroter Farbe und färbt auf Wolle und Haar ein sehr gut säurewalkechtes und lichtechtes Blau.
Additional patent to the main patent No. 194456. The subject of this patent is a process for the production of a disazo dye, which is characterized in that the tetrazo compound of benzidinesulfon-disulfonic acid (Beilstein, IV. Edition., Vol. XVHI, p.
636) couples with 2 molecules of the toluenesulfonic acid ester of 2-atnino-8-oxytraphthalite-6-sulfonic acid and cleaves the toluenesulfonic acid residues from the disazo dye obtained.
The disazo carbate crystallizes in fine, blue needles, dissolves in water with a pure blue, in concentrated sulfuric acid with a violet-red color and is identical to the product shown according to additional patent no. 199655.
Example; 40.6 g of benzidinesulfone disulfonic acid are mixed with 13.8 g of sodium nitrite and 60 g of conc. Hydrochloric acid tetrazotized in a known manner and the tetrazo compound obtained is coupled in the presence of sodium acetate with 78.6 g of the toluenesulfonic acid ester of 2-amirto-8-oxy-ttaphthalite-6-sulfonic acid.
The violet disazo carbate thus obtained is filtered off, dried and concentrated in ten times the amount. Stir in sulfuric acid. The temperature is then increased to 75-80 by careful addition of water, the dye dissolving with elimination of the toluenesulfonic acid residues. When the saponification is complete, the sulfuric acid solution is poured into a mixture of water and ice and the disazo dye which has separated out is isolated.
The disazo dye crystallizes in fine blue needles, dissolves in water with a pure blue color, in concentrated sulfuric acid with a purple-red color and dyes wool and hair a very good acid-walnut and lightfast blue.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH194456T | 1937-03-08 | ||
| CH202163T | 1937-03-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH202163A true CH202163A (en) | 1938-12-31 |
Family
ID=25722684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH202163D CH202163A (en) | 1937-03-08 | 1937-03-08 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH202163A (en) |
-
1937
- 1937-03-08 CH CH202163D patent/CH202163A/en unknown
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