CH278470A - Process for preparing a metallized azo dye. - Google Patents
Process for preparing a metallized azo dye.Info
- Publication number
- CH278470A CH278470A CH278470DA CH278470A CH 278470 A CH278470 A CH 278470A CH 278470D A CH278470D A CH 278470DA CH 278470 A CH278470 A CH 278470A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- chromium
- preparing
- sub
- metallized azo
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000000975 dye Substances 0.000 claims description 6
- 150000001845 chromium compounds Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000006172 buffering agent Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FQHYQCXMFZHLAE-UHFFFAOYSA-N 25405-85-0 Chemical compound CC1(C)C2(OC(=O)C=3C=CC=CC=3)C1C1C=C(CO)CC(C(C(C)=C3)=O)(O)C3C1(O)C(C)C2OC(=O)C1=CC=CC=C1 FQHYQCXMFZHLAE-UHFFFAOYSA-N 0.000 description 1
- ROCAGPQIOKKIOE-UHFFFAOYSA-N 3-(2-ethoxyphenyl)-3-oxopropanenitrile Chemical compound CCOC1=CC=CC=C1C(=O)CC#N ROCAGPQIOKKIOE-UHFFFAOYSA-N 0.000 description 1
- RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229960000359 chromic chloride Drugs 0.000 description 1
- -1 chromium naphthalene disulfonate Chemical compound 0.000 description 1
- ABXXWVKOBZHNNF-UHFFFAOYSA-N chromium(3+);dioxido(dioxo)chromium Chemical compound [Cr+3].[Cr+3].[O-][Cr]([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Cr]([O-])(=O)=O ABXXWVKOBZHNNF-UHFFFAOYSA-N 0.000 description 1
- 235000007831 chromium(III) chloride Nutrition 0.000 description 1
- 239000011636 chromium(III) chloride Substances 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- 235000015217 chromium(III) sulphate Nutrition 0.000 description 1
- 239000011696 chromium(III) sulphate Substances 0.000 description 1
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 1
- 238000004040 coloring 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
- 238000004043 dyeing Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- QAYQKAPOTVSWLS-UHFFFAOYSA-N methyl 2-ethoxybenzoate Chemical compound CCOC1=CC=CC=C1C(=O)OC QAYQKAPOTVSWLS-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Coloring (AREA)
- Optical Filters (AREA)
Description
<B>Procédé de préparation d'un colorant azoïque métallisé.</B> Le présent brevet a pour objet un procédé de préparation d'un nouveau colorant azoïque métallisé d'une valeur particulière pour la teinture de la laine.
Selon l'invention, ce colorant azoïque mé tallisé est préparé en faisant réagir un com posé de chrome avec une matière colorante azoïque ayant la formule
EMI0001.0002
Il résulte de cette réaction un composé complexe du chrome et (le la matière colorante azoïque.
Le composé de chrome préféré est. l'acétate basique de chrome. Cependant, on peut em ployer d'autres composés de chrome, comme l'hydroxyde chromique, l'acétate chromique, les formiate, fluorure, chlorure chromiques, la chlorure basique de chrome, le sulfate chro- mique, le sulfate basique de chrome, le hen- zène-sulfonate de chrome, les naphtalène-di- sulfonates de chrome et le chromate ehro- mique.
1)e préférence, la réaction est effectuée par traitement d'une solution aqueuse des corps réagissants au reflux jusqu'à ce que le colorant azoïque métallisé se soit précipité. Divers agents tampons, tels que acides, bases, etc., peuvent être présents, si on le désire, pour contrôler le p$.
L'invention sera décrite avec plus de dé tails dans l'exemple suivant. Les parties s'en tendent en poids. , <I>Exemple:</I> Le colorant azoïque correspondant â, la formule suivante
EMI0001.0017
peut être obtenu par copulation du composé diazoïque de l'acide 1-amino-2-hydroxy-4- naphtalène-sulfonique avec le 2-éthoxy-benzoyl- acétonitrile en solution alcaline. Le colorant est métallisé comme suit Un mélange de 4?5 parties d'eau et de 46,1 parties \du colorant est. traité avec 207 parties en volume d'une solution d'acétate basique de chrome contenant 7,8 g de chrome.
Après traitement. de la, solution au reflux pen dant peu de temps, environ 140 parties d'acide sulfurique 5 N sont. ajoutées. On continue de traiter au reflux jusqu'à ce que la métallisa tion soit complète. Le produit. est alors re froidi et filtré. Le produit. est lavé et séché à 50-55 C. On obtient. un rendement excel- lent. Le nouveau colorant teint la laine en bain acide en un bordeaux brillant ayant une excellente résistance à la lumière, au lavage et au foulage.
Le '->-éthoxy-benzoylacétonitrile employé peut être préparé comme suit: Un mélange de<B>18,0</B> parties de 2-éthoxy- benzoate de méthyle, 5,1 parties d'acétonitrile et 5,7 parties de méth@-1ate de sodium à 9511/o est agité vigoureusement à une température de 80 et graduellement. chauffé à. l00 C. Le mélange de réaction est. d'abord épais, puis devient fluide et finalement donne une pâte épaisse. On continue de chauffer à.1.00-1.05 C pendant deux autres Heures.
Le mélange de réaction est refroidi et traité avec 100 parties d'eau. La solution résultante est filtrée et aci difiée pour précipiter le produit qui est filtré et lavé avec une solution de bicarbonate. Il peut être recristallisé d'une solution alcooli que. Le point de fusion de la substance pure est de 1210C environ.
<B> Process for the preparation of a metallic azo dye. </B> The present patent relates to a process for the preparation of a new metallic azo dye of particular value for dyeing wool.
According to the invention, this metallized azo dye is prepared by reacting a chromium compound with an azo dye having the formula
EMI0001.0002
This reaction results in a complex compound of chromium and (the azo coloring matter.
The preferred chromium compound is. basic chromium acetate. However, other chromium compounds can be used, such as chromic hydroxide, chromic acetate, formate, fluoride, chromic chloride, basic chromium chloride, chromium sulphate, basic chromium sulphate, chromium henzene sulfonate, chromium naphthalene disulfonate and chromium chromate.
1) Preferably, the reaction is carried out by treating an aqueous solution of the reactants under reflux until the metallized azo dye has precipitated out. Various buffering agents, such as acids, bases, etc., can be present, if desired, to control the p $.
The invention will be described in more detail in the following example. The parties get along in weight. , <I> Example: </I> The azo dye corresponding to â, the following formula
EMI0001.0017
can be obtained by coupling the diazo compound of 1-amino-2-hydroxy-4-naphthalenesulfonic acid with 2-ethoxy-benzoyl-acetonitrile in alkaline solution. The dye is metallized as follows A mixture of 4-5 parts of water and 46.1 parts of the dye is. treated with 207 parts by volume of a solution of basic chromium acetate containing 7.8 g of chromium.
After treatment. of the solution under reflux for a short time, about 140 parts of 5N sulfuric acid are. added. The reflux treatment is continued until the metallization is complete. The product. is then re-cooled and filtered. The product. is washed and dried at 50-55 C. We obtain. excellent performance. The new dye dyes the wool in an acid bath to a shiny burgundy with excellent resistance to light, washing and crushing.
The '-> - ethoxy-benzoylacetonitrile employed can be prepared as follows: A mixture of <B> 18.0 </B> parts of methyl 2-ethoxy-benzoate, 5.1 parts of acetonitrile and 5.7 parts of 9511% sodium meth @ -1ate is stirred vigorously at a temperature of 80 and gradually. heated to. 100 C. The reaction mixture is. first thick, then becomes fluid and finally gives a thick paste. We continue to heat at 1.00-1.05 C for two more hours.
The reaction mixture is cooled and treated with 100 parts of water. The resulting solution is filtered and acidified to precipitate the product which is filtered and washed with a bicarbonate solution. It can be recrystallized from an alcoholic solution. The melting point of the pure substance is about 1210C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US278470XA | 1942-09-16 | 1942-09-16 | |
| CH274239T | 1947-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH278470A true CH278470A (en) | 1951-10-15 |
Family
ID=25731527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH278470D CH278470A (en) | 1942-09-16 | 1947-09-15 | Process for preparing a metallized azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH278470A (en) |
-
1947
- 1947-09-15 CH CH278470D patent/CH278470A/en unknown
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