CH268762A - Process for the preparation of a new disazo dye. - Google Patents
Process for the preparation of a new disazo dye.Info
- Publication number
- CH268762A CH268762A CH268762DA CH268762A CH 268762 A CH268762 A CH 268762A CH 268762D A CH268762D A CH 268762DA CH 268762 A CH268762 A CH 268762A
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- sulfuric acid
- preparation
- new
- converted
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- -1 amino-azo compound Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 3
- 235000005811 Viola adunca Nutrition 0.000 claims description 2
- 240000009038 Viola odorata Species 0.000 claims description 2
- 235000013487 Viola odorata Nutrition 0.000 claims description 2
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 230000001180 sulfating effect Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005001 aminoaryl group Chemical group 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/78—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with other reactive groups
- C09B62/82—Azo dyes
- C09B62/83—Disazo or polyazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 263980. Verfahren zur Herstellung eines neuen Disazofarbstoffes. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen Disazofarbstoffes, welches dadurch gekenn zeichnet ist, dass man p-Aminophenyl fl-oxy- äthyl-ätlier, ein Sulfatierungsmittel., ein Diazo- tierungsmittel, p-Xylidin und o-Oxydiphenyl derart zusammen umsetzt,
dass die Oxyalkyl- gruppe in die entsprechende Schwefelsäure ester-Gruppe übergeführt, die Aminoaryl- oxyalkviätlier-Vei-biiiduiig dianotiert und in der p-Stellung zur Aminogruppe des p-Xyli- dins gekuppelt wird, und die auf diese Weise gebildete Aininoazoverbindung weiter diano tiert:
und in der p-Stellung zur Hydroxyl- gruppe des o-Oxycliplienyls gekuppelt wird.
Der neue Farbstoff ist: ein grauviolettes Pulver, (las sich in Wasser unter Bildung einer oran -en Lösung und in konz. Schwefel säure unter Bildung einer blauvioletten Lö sung löst.
Als Sitlfatierungsmittel kann man Schwe felsäure und als Diazotierungsniittel. salpetrige Säure verwenden.
Die Oxyalky-lgruppe kann vor oder nach den Kupplungsreaktionen oder zwischen den beiden Kupplungsreaktionen mit Schwefel- si-e in die entsprechende Scliwefelsäureester- Uruppe übergeführt werden.
<I>Beispiel,:</I> plan diazoniert 23,3 Teile p-Aminopheny l- /3-oxyätliyliitlier-scliwefelsäureester, kuppelt die Diazoverbindung mit 12,1 Teilen p-Xyii- din und dianotiert die erhaltene Aminomono- azo-Verbindung nach den An aaben von Bei- spiel 3 des brit. Patentes Nr.
455643. Man suspendiert die Diazomonoazo-Verbindung in Wasser, kühlt die Suspension auf 5-7.00 C ab und trägt sie in eine in ähnlicher Weise ge kühlte und kräftig gerührte Lösung von 17 Teilen o-Oxydiphenyl., 4 Teilen Natrium- hy droxy d -und 10 Teilen wasserfreiem Na- triumcarbonat in 200 Teilen Wasser ein. Nach beendeter Kupplung wird der neue Farbstoff durch Zugabe von 10 /o gewöhnlichem Salz (Gew. pro Volumen) gefällt, abfiltriert und schliesslich getrocknet.
<B> Additional patent </B> to main patent no. 263980. Process for the production of a new disazo dye. The subject of the present patent is a process for the preparation of a new disazo dye, which is characterized in that p-aminophenyl fl-oxy-ethyl-ätlier, a sulfating agent., A diazotizing agent, p-xylidine and o-oxydiphenyl together in this way implements,
that the oxyalkyl group is converted into the corresponding sulfuric acid ester group, the aminoaryl oxyalkviätlier-Vei-biiiduiig dianotated and coupled in the p-position to the amino group of the p-xylidine, and the aminoazo compound formed in this way is further dianoated :
and is coupled in the p-position to the hydroxyl group of the o-oxycliplienyl.
The new dye is: a gray-violet powder (can be dissolved in water to form an orange solution and in concentrated sulfuric acid to form a blue-violet solution.
Sulfur acid can be used as the surfactant and the diazotization agent. use nitrous acid.
The oxyalkyl group can be converted into the corresponding sulfuric acid ester group before or after the coupling reactions or between the two coupling reactions with sulfuric acid.
<I> Example: </I> plan diazonized 23.3 parts of p-aminophenyl- / 3-oxyätliyliitlier-sulfuric acid ester, couples the diazo compound with 12.1 parts of p-xyiidine and dianotates the resulting aminomono- azo compound according to the details of example 3 of British patent no.
455643. The diazomonoazo compound is suspended in water, the suspension is cooled to 5-7.00 C and it is added to a similarly cooled and vigorously stirred solution of 17 parts of o-oxydiphenyl., 4 parts of sodium hydroxide - and 10 parts of anhydrous sodium carbonate in 200 parts of water. After the coupling has ended, the new dye is precipitated by adding 10 / o common salt (weight per volume), filtered off and finally dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB268762X | 1946-03-11 | ||
| CH263980T | 1947-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH268762A true CH268762A (en) | 1950-05-31 |
Family
ID=25730703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH268762D CH268762A (en) | 1946-03-11 | 1947-03-10 | Process for the preparation of a new disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH268762A (en) |
-
1947
- 1947-03-10 CH CH268762D patent/CH268762A/en unknown
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