CH313493A - Process for the preparation of a new diazo-amino derivative - Google Patents
Process for the preparation of a new diazo-amino derivativeInfo
- Publication number
- CH313493A CH313493A CH313493DA CH313493A CH 313493 A CH313493 A CH 313493A CH 313493D A CH313493D A CH 313493DA CH 313493 A CH313493 A CH 313493A
- Authority
- CH
- Switzerland
- Prior art keywords
- diazo
- hydroxy
- arylides
- carboxylic
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 diazo-amino Chemical class 0.000 title claims 2
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical class N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- DHBHUGJZAZYELM-UHFFFAOYSA-N 2-(butylamino)benzoic acid Chemical compound CCCCNC1=CC=CC=C1C(O)=O DHBHUGJZAZYELM-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- HQOBDLCAOWRBOU-UHFFFAOYSA-N 2-hydroxy-9h-carbazole-1-carboxylic acid Chemical compound C12=CC=CC=C2NC2=C1C=CC(O)=C2C(=O)O HQOBDLCAOWRBOU-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 150000001261 hydroxy acids Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- PSAGPCOTGOTBQB-UHFFFAOYSA-N 4-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(O)C2=C1 PSAGPCOTGOTBQB-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- CZIRZNRQHFVCDZ-UHFFFAOYSA-L titan yellow Chemical compound [Na+].[Na+].C1=C(C)C(S([O-])(=O)=O)=C2SC(C3=CC=C(C=C3)/N=N/NC3=CC=C(C=C3)C3=NC4=CC=C(C(=C4S3)S([O-])(=O)=O)C)=NC2=C1 CZIRZNRQHFVCDZ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Coloring (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Paper (AREA)
Description
Procédé de préparation d'un nouveau dérivé diazo-aminé Le présent brevet a pour objet un procédé de préparation d'un nouveau dérivé diazo- aminé, procédé caractérisé en ce que l'on condense un composé diazoïque dérivé de l'amino-1-méthoxy-2-nitro-4-benzène, en mi lieu non acide, avec l'acide N-butyl-anthrani- lique.
Dans l'exemple qui est donné ci-dessous, les parties en poids et les parties en volume sont entre elles dans le même rapport que les kilogrammes et les litres. <I>Exemple</I> <B>16,8</B> parties en poids d'amino-1-méthoxy- 2-nitro-4-benzène sont empâtées dans<B>30</B> par ties en volume d'acide chlorhydrique<B>à</B> 20o Bé et<B>50</B> parties d'eau pendant quelques heures. On refroidit<B>à 00 C</B> et ajoute<B>50</B> parties en poids de glace. On diazote avec 14 parties en volume d'une solution de nitrite de sodium<B>à</B> <B>50</B> % en volume. On brasse pendant une heure.
On prépare par ailleurs une solution de 24 parties en poids d'acide N-butyl-anthrani- lique dans<B>300</B> parties d'eau et la quantité suf fisante de carbonate de sodium pour amener <B>à</B> dissolution, puis on ajoute encore<B>30</B> par ties en poids de carbonate de sodium. La so- lution diazoïque précédente est coulée sous liquide dans la solution du stabilisateur. L'ab sorption du composé diazoïque est très rapide.
Dès la fin de la coulée, on alcalinise avec une solution de soude caustique jusqà'à très nette réaction sur papier au jaune thiazol. Le dérivé diazo-aminé est précipité par addition de<B>100</B> parties en poids de sel ordinaire. D'abord<B>pâ-</B> teux, le produit cristallise peu<B>à</B> peu. Le ren dement dépasse<B>80</B> %.
Le dérivé diazo-aminé obtenu se présente sous la forme de cristaux de couleur orangé brunâtre.<B>Il</B> est stable<B>à</B> l'état sec et soluble dans l'eau. Il peut être utilisé en mélange avec des copulants divers. Les pâtes d'impression, préparées avec ces mélanges suivant la ma nière habituelle en présence d'un léger excès de soude, imprimées sur tissu de coton par exemple et vaporisées en milieu neutre ou acide, permettent d'obtenir une grande variété de nuances.
On obtient ainsi avec les aryhdes de l'acide fl-hydroxy-naphthoïque des nuances rouge bleuté<B>à</B> bordeaux, avec les aryhdes des acides hydroxy-carbazole-carboxylique ou hy- droxy <B>-</B> diphénylèneoxyde <B>-</B> carboxylique, des nuances brunes, avec les arylides de l'acide hydroxy <B>-</B> benzocarbazole <B>-</B> carboxylique, des nuances noires.
Process for the preparation of a new diazo-amine derivative The present patent relates to a process for the preparation of a new diazo-amine derivative, process characterized in that a diazo compound derived from amino-1- is condensed. methoxy-2-nitro-4-benzene, in a non-acidic place, with N-butyl-anthranilic acid.
In the example given below, the parts by weight and the parts by volume are in the same ratio as the kilograms and the liters. <I> Example </I> <B> 16.8 </B> parts by weight of amino-1-methoxy-2-nitro-4-benzene are paste in <B> 30 </B> parts in volume of hydrochloric acid <B> at </B> 20o Bé and <B> 50 </B> parts of water for a few hours. Cool to <B> 00 C </B> and add <B> 50 </B> parts by weight of ice. Diazotized with 14 parts by volume of a <B> </B> <B> 50 </B>% by volume sodium nitrite solution. We brew for an hour.
A solution of 24 parts by weight of N-butyl-anthranilic acid in <B> 300 </B> parts of water and the sufficient quantity of sodium carbonate is also prepared to bring <B> to < / B> dissolution, then a further <B> 30 </B> parts by weight of sodium carbonate are added. The above diazo solution is poured under liquid into the stabilizer solution. The absorption of the diazo compound is very rapid.
From the end of the casting, basification is carried out with a caustic soda solution until a very clear reaction on thiazol yellow paper. The diazo-amine derivative is precipitated by adding <B> 100 </B> parts by weight of common salt. First <B> pale </B>, the product crystallizes little <B> to </B> little. The yield exceeds <B> 80 </B>%.
The diazo-amine derivative obtained is in the form of crystals of brownish orange color. <B> It </B> is stable <B> in </B> dry state and soluble in water. It can be used as a mixture with various couplers. Printing pastes, prepared with these mixtures in the usual way in the presence of a slight excess of sodium hydroxide, printed on cotton fabric for example and sprayed in a neutral or acidic medium, make it possible to obtain a wide variety of shades.
We thus obtain with the aryhds of fl-hydroxy-naphthoic acid bluish red shades <B> to </B> burgundy, with the aryhds of hydroxy-carbazole-carboxylic or hydroxy acids <B> - </ B > diphenyleneoxide <B> - </B> carboxylic, brown undertones, with arylides of hydroxy <B> - </B> benzocarbazole <B> - </B> carboxylic acid, black undertones.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR313493X | 1952-07-17 | ||
| FR60253X | 1953-02-06 | ||
| CH310501T | 1953-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH313493A true CH313493A (en) | 1956-04-15 |
Family
ID=27178332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH313493D CH313493A (en) | 1952-07-17 | 1953-06-30 | Process for the preparation of a new diazo-amino derivative |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH313493A (en) |
-
1953
- 1953-06-30 CH CH313493D patent/CH313493A/en unknown
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