AT55689B - Process for the preparation of disazo dyes. - Google Patents
Process for the preparation of disazo dyes.Info
- Publication number
- AT55689B AT55689B AT55689DA AT55689B AT 55689 B AT55689 B AT 55689B AT 55689D A AT55689D A AT 55689DA AT 55689 B AT55689 B AT 55689B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- parts
- disazo dyes
- dyes
- acid
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 10
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- -1 aminoazo Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Description
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Verfahren zur Darstellung von Disazofarbstoffen.
EMI1.1
EMI1.2
EMI1.3
Säuren vereinigt, die Produkte nach erfolgter Diazotierung mit 1.3-Naphtolsulfosäure kuppelt und aus den auf diese Weise erhältlichen Farbstoffen die Azidylgruppe abspaltet.
Man erl) ält so blaue Banmwollfarbstoffe, die sich auf der Faser diazotieren und entwickeln lassen. Durch Entwickeln mit #-Napthol gewinnt man klare grünblaue Nuancen von vorzüglicher Waschechtheit und guter Lichtechtheit, die sich dadurch auszeichnen, dass sie sich mit Hydrosulfit vorzüglich weiss ätzen lassen. Die neuen Produkte unterscheiden sich von den analogen Farbstoffen, die die 2-Naphtol-6-sulfosäure in Endstellung enthalten, dtirf'h ihre wertvolleren grünstichigen Nuancen, die man mit diesen Farbstoffen nicht erzielen kann und durch bessere Wasser- und Bügelechtheit.
Beispiel.
215Teile5-Amino-4-chor-2-azetylamino-1-anisol
EMI1.4
werden mit 7000 Teilen Wasser angerührt, mit 2f) 0 Teilen Salzsäure (190 Bé) versetzt und bei 10 mit 69 Teilen natriumnitrit diazotiert. Die erhaltene Diazoverbindung lässt man darauf in eine Lösung von 245 Teilen 1-naphtylamin-6-sulfosaurem natrium einfliessen, die mit 250 Teilen Natriumazetat von 1000/0 versetzt ist. Die Kuppelung ist nach wenigen Minuten beendet. Die Mischung wird darauf mit Salzsäure mineralsauer gemacht und der Aminoazofarbstoff bei 10 mit 69 Teilen Natriumnitrit abermals diazotiert.
Nach etwa 1 Stunde ist dio Diazotierung beendet. Man lässt darauf die Diazoazoverbindung in eine auf 0 gekühlte Lüsung von 246 Teilen 1-naphtol-3-sulfosaurem Natrium in Wasser
EMI1.5
in 7000 Teilf'n heissem Wasser gelöst und der Farbstoff durch 1stündiges Kochen mit 1400 Teilem 30 . iger Natronlauge verseift wird. Die heisse Lösung wird sofort mit kaltem Wasser gekühlt, die überschüssige Natronlauge abgestumpft und der Farbstoff abfiltriert.
Er färbt Baumwollp direkt in blauen Tönen an ; die Färbung geht durch Diazotieren und Entwickeln mit #-Naphtol in ein klares grünstichiges Blau von vorzüglicher Wasch- t'chtheit über.
In derselben Weise verfährt man hei Verwendung des entsprechenden Phenetols oder der 1. 7-Naphtylainsulfosäure.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
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Process for the preparation of disazo dyes.
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EMI1.2
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Acids are combined, the products are coupled with 1,3-naphthol sulfonic acid after diazotization has taken place and the azidyl group is split off from the dyes obtainable in this way.
You can get blue banm wool dyes that can be diazotized and developed on the fiber. Developing with # -napthol gives clear green-blue nuances of excellent washfastness and good lightfastness, which are distinguished by the fact that they can be etched with hydrosulfite to an excellent white. The new products differ from the analogous dyes, which contain 2-naphthol-6-sulfonic acid in the end position, because of their more valuable greenish nuances, which cannot be achieved with these dyes, and because of their better water and ironing resistance.
Example.
215Parts 5-Amino-4-chloro-2-acetylamino-1-anisole
EMI1.4
are stirred with 7000 parts of water, treated with 2f) 0 parts of hydrochloric acid (190 Be) and diazotized at 10 with 69 parts of sodium nitrite. The diazo compound obtained is then allowed to flow into a solution of 245 parts of 1-naphthylamine-6-sulphonic acid sodium to which 250 parts of 1000/0 sodium acetate are added. The coupling is completed after a few minutes. The mixture is then made mineral acid with hydrochloric acid and the aminoazo dye is diazotized again at 10 with 69 parts of sodium nitrite.
The diazotization has ended after about 1 hour. The diazoazo compound is then added to a solution, cooled to 0, of 246 parts of 1-naphthol-3-sulphonic acid sodium in water
EMI1.5
dissolved in 7000 parts of hot water and the dye by boiling for 1 hour with 1400 parts 30. iger caustic soda is saponified. The hot solution is immediately cooled with cold water, the excess sodium hydroxide solution is truncated and the dye is filtered off.
He stains cotton directly in blue tones; the color changes to a clear greenish blue of excellent washfastness as a result of diazotization and development with # -naphtol.
The same procedure is used when using the corresponding phenetol or 1. 7-naphtylainsulfonic acid.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE55689X | 1910-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT55689B true AT55689B (en) | 1912-10-10 |
Family
ID=5628493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT55689D AT55689B (en) | 1910-06-15 | 1911-05-15 | Process for the preparation of disazo dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT55689B (en) |
-
1911
- 1911-05-15 AT AT55689D patent/AT55689B/en active
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