CH238464A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH238464A CH238464A CH238464DA CH238464A CH 238464 A CH238464 A CH 238464A CH 238464D A CH238464D A CH 238464DA CH 238464 A CH238464 A CH 238464A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- production
- parts
- yellow
- pyrazolone
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 229920000297 Rayon Polymers 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- -1 maleic acid ester Chemical class 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical group CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008096 xylene 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paper (AREA)
Description
Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, dass man einen neuen Azofarbstoff erhält, wenn man 1 Mol diazo- tiertes 1-Aminobenzol-4-ss-ogyäthyl-sulfon., 1 Mol 1-(2'-Chlor)-phenyl-3-methyl-5-pyrazo- lon und 1 Mol Maleinsäureanhydrid derart aufeinander einwirken lässt,
dass die Diazo- verbindung in 4-Stellung des Pyrazolonkernes eingreift und dass die Ogygruppe des Ogy- äthylsulfonrestes zu einem sauren Malein- säureester verestert wird.
Der neue Farbstoff ist ein gelboranges Pulver, das sich in Wasser klar mit gelber Farbe löst und Acetatkunstseide aus neutra ler wässeriger Lösung unter Zusatz von Na triumsulfat in reinen gelben Tönen von vor züglichen Echtheitseigenschaften färbt.
Beispiel: 20,1 Teile 1-Aminobenzol-4-ss-ogyäthyl- sulfon werden mit 25 Teilen 30%iger Salz säure in 50 Teilen Wasser gelöst und bei 5 bis 10 mit 25 Teilen 4-n-Natriumnitritlösung diazotiert. Die klare, gelborange Diazolösung lässt man bei 5-10 zu einer Lösung von 21 Teilen 1-(2'-Chlor)-phenyl-3-methyl-5-pyr- azolon, 15 Teilen 30%iger Natronlauge und 25 Teilen Natriumcarbonat in 200 Teilen Wasser fliessen.
Man rührt bis zur Beendi gung der Farbstoffbildung bei 10-15 , saugt dann den unlöslichen Farbstoff ab, wäscht mit 200 Teilen Wasser und trocknet bei 50 bis 60 .
42 Teile des so erhaltenen Farbstoffes werden bei 60-70 in 200 Teilen T'oluol ge löst und in eine Lösung 12 Teile Maleinsäure- anhydrid eingetragen. Man erwärmt einige Zeit auf 100-110 , destilliert dann den grössten Teil des Lösungsmittels im Vakuum ab, lässt erkalten, presst ab und wäscht den Rückstand mit wenig Alkohol. Den Filter rückstand löst man mit der nötigen Menge Natriumcarbonat in 400 Teilen Wasser von 20-30 . Aus der klaren Lösung wird das Natriumsalz des Farbstoffes durch Zugabe von 50 Teilen Natriumchlorid gefällt.
Man saugt ab, wäscht mit 10%iger Natriumchlo- ridlösung und trocknet im Vakuum bei 50 bis 55 . Als Lösungsmittel für die Vereste- rung können ausser Toluol auch andere ge eignete Lösungsmittel, wie Benzol, Xylol usw. oder Eisessig verwendet werden.
Process for the production of a new azo dye. It has been found that a new azo dye is obtained if 1 mole of diazotized 1-aminobenzene-4-ss-ogyäthyl-sulfon., 1 mole of 1- (2'-chloro) -phenyl-3-methyl-5- pyrazolone and 1 mole of maleic anhydride can act on one another in such a way that
that the diazo compound intervenes in the 4-position of the pyrazolone nucleus and that the ogy group of the ogy ethylsulfone residue is esterified to an acidic maleic acid ester.
The new dye is a yellow-orange powder that dissolves in water with a clear yellow color and dyes acetate rayon from neutral aqueous solution with the addition of sodium sulfate in pure yellow shades with excellent fastness properties.
Example: 20.1 parts of 1-aminobenzene-4-ss-ogyäthylsulfon are dissolved with 25 parts of 30% hydrochloric acid in 50 parts of water and diazotized at 5 to 10 with 25 parts of 4-n-sodium nitrite solution. The clear, yellow-orange diazo solution is added at 5-10 to a solution of 21 parts of 1- (2'-chloro) -phenyl-3-methyl-5-pyrazolone, 15 parts of 30% strength sodium hydroxide solution and 25 parts of sodium carbonate in 200 Share water flow.
The mixture is stirred until the formation of the dye is at 10-15, then the insoluble dye is filtered off with suction, washed with 200 parts of water and dried at 50 to 60.
42 parts of the dye thus obtained are dissolved at 60-70 in 200 parts of toluene and 12 parts of maleic anhydride are introduced into a solution. The mixture is heated to 100-110 for some time, then most of the solvent is distilled off in vacuo, left to cool, pressed off and the residue is washed with a little alcohol. The filter residue is dissolved with the necessary amount of sodium carbonate in 400 parts of 20-30 water. The sodium salt of the dye is precipitated from the clear solution by adding 50 parts of sodium chloride.
It is suctioned off, washed with 10% sodium chloride solution and dried in vacuo at 50 to 55. In addition to toluene, other suitable solvents such as benzene, xylene, etc. or glacial acetic acid can also be used as solvents for the esterification.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH236764T | 1943-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH238464A true CH238464A (en) | 1945-07-15 |
Family
ID=4459600
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH238463D CH238463A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
| CH238462D CH238462A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
| CH238460D CH238460A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
| CH238461D CH238461A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
| CH238465D CH238465A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
| CH238464D CH238464A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
| CH236764D CH236764A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
| CH238466D CH238466A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
Family Applications Before (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH238463D CH238463A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
| CH238462D CH238462A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
| CH238460D CH238460A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
| CH238461D CH238461A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
| CH238465D CH238465A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH236764D CH236764A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
| CH238466D CH238466A (en) | 1943-09-02 | 1943-09-02 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (8) | CH238463A (en) |
-
1943
- 1943-09-02 CH CH238463D patent/CH238463A/en unknown
- 1943-09-02 CH CH238462D patent/CH238462A/en unknown
- 1943-09-02 CH CH238460D patent/CH238460A/en unknown
- 1943-09-02 CH CH238461D patent/CH238461A/en unknown
- 1943-09-02 CH CH238465D patent/CH238465A/en unknown
- 1943-09-02 CH CH238464D patent/CH238464A/en unknown
- 1943-09-02 CH CH236764D patent/CH236764A/en unknown
- 1943-09-02 CH CH238466D patent/CH238466A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH238465A (en) | 1945-07-15 |
| CH238460A (en) | 1945-07-15 |
| CH238461A (en) | 1945-07-15 |
| CH236764A (en) | 1945-03-15 |
| CH238463A (en) | 1945-07-15 |
| CH238462A (en) | 1945-07-15 |
| CH238466A (en) | 1945-07-15 |
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