CH301805A

CH301805A - Process for the preparation of the disodium salt of the 2,4-dimethoxybenzoyl derivative of 5,5'-dichloro-4,4'-diaminostilbene-2,2'-disulphonic acid.

Info

Publication number: CH301805A
Authority: CH
Inventors: Company American Cyanamid
Original assignee: American Cyanamid Co
Priority date: 1951-07-17
Filing date: 1952-07-16
Publication date: 1954-09-30

Description

Procede de preparation du sel disodique du derive 2,4-dimethoxybenzoylique de 1'acide 5,5'- dichloro-4,4'-diaminostilbene-2,2'-disulfonique. La presente Invention se rapporte ä la pre- para.tion du sel disodique du derive 2,4-di- methoxybenzoylique de 1'acide 5,5'-dichloro- 4,4'-diaminostilbene-2,2'-disulfonique de for- mule Process for the preparation of the disodium salt of the 2,4-dimethoxybenzoyl derivative of 5,5'-dichloro-4,4'-diaminostilbene-2,2'-disulphonic acid. The present invention relates to the preparation of the disodium salt of the 2,4-dimethoxybenzoyl derivative of 5,5'-dichloro-4,4'-diaminostilbene-2,2'-disulphonic acid of form - mule

Suivant 1'invention, an prepare ce com- pose en faisant reagir un halogenure de 2,4- dim6thoxybenzoyle avec de 1'acide 5,5'-di- chloro-4,4'-diaminostilbene-2,2'-disulfonique et en traita.nt 1e produit de la reaction avec un sel de sodium pour Former 1e sel disodique du derive 2,4-dimethoxybenzoylique dudit acide. Le compose obtenu constitue un Corps solide jaune qui se decompose, sans Fusion, ä des temperatures elevees, et qui est faiblement soluble dans 1'eau et un peu plus soluble dans de 1'aleool aqueux et de la. pyridine aqueuse. According to the invention, this compound is prepared by reacting a 2,4-dim6thoxybenzoyl halide with 5,5'-dichloro-4,4'-diaminostilbene-2,2'-disulphonic acid and treating the first reaction product with a sodium salt to form the first disodium salt of the 2,4-dimethoxybenzoyl derivative of said acid. The compound obtained constitutes a yellow solid body which decomposes, without melting, at elevated temperatures, and which is slightly soluble in water and slightly more soluble in aqueous alcohol and salt. aqueous pyridine.

Ce compose se laisse facilement transfor- mer en 1'acide libre par addition d'un acide et peut, en outre, eire transforme en sel d'am- monium ou en d'autres sels alcalins. This compound is easily converted into the free acid by addition of an acid and can further be converted into the ammonium salt or other alkaline salts.

Le produit en cause constitue un agent eclaireissant fluoreseent qui possede ä un tres haut de-r6 les proprietes desirees pour un produit de ce genre et qui sont: pouvoir fluorescent, affinite, resistance ä 1'hypochlo- rite et 1a, propriete de ne pas modifier.la Cou leur soit des detergents, soit des tissus. Dans la preparation d'agents eclaircissants, an ne pouvait en general obtenir certaines de ces proprietes qu'au detriment des autres. Cela etait particulierement 1e cas pour la resistance au blanchiment ä 1'hypochlorite et 1'action mo- difiante Sur les detergents, qui constituaient 1e point Faible des agents d'eclaircissement ordinaires du type de 1'acide diaminostilbAne- sulfonique. The product in question constitutes a fluorescing illuminating agent which has, at a very high de-r6, the properties desired for a product of this type and which are: fluorescent power, affinity, resistance to hypochlorite and the property of not change.the color either of the detergents or of the fabrics. In the preparation of lightening agents, one could generally obtain some of these properties only at the expense of others. This was particularly the case for the resistance to hypochlorite bleaching and the modifying action on detergents, which constituted the weak point of the ordinary bleaching agents of the diaminostilbanesulfonic acid type.

Le produit obtenu suivant la presente In- vention, par contre, est exempt de Ces desavan- tages. Il possede non seulement une affinite et un pouvoir fluorescent eleves, mais est aussi exempt ä un degre surprenant de la tendance ä modifier la Couleur des detergents ou des tissus. En outre, il presente une excellente resistance ä 1'action d'hypochlorites, de Sorte qu'il peut etre applique sans aucune diffi- culte avant ou pendant 1'operation de blan- chiment. The product obtained according to the present invention, on the other hand, is free from these disadvantages. It not only possesses high affinity and fluorescent power, but is also surprisingly free from the tendency to alter the color of detergents or fabrics. Furthermore, it presents an excellent resistance to the action of hypochlorites, so that it can be applied without any difficulty before or during the bleaching operation.

L'acide libre ainsi que 1e sel d'ammonium et d'autres sels alcalins peuvent egalement etre utilises comme agents eelaircissants et possedent des proprietes analogues ä celles du sel disodique. The free acid as well as the ammonium salt and other alkaline salts can also be used as bleaching agents and have similar properties to the disodium salt.

L'utilisation du produit obtenu suivant 1'invention n'est pas limitee au traitement dune fibre particuliere; au contraire, il con- vient au traitement de fibres animales aussi bien que de fibres vegetales et de fibres syn- thetiques, telles que par exemple de fibres de soie artificielle, de nylon, etc. L'utilisation de ce produit n'est, en outre, pas limitee au trai- tement de matieres textiles. Il peiit egalement etre utilise avec avantage dans la fabrication du Papier et de produits feutres, de feuilles ou pellicules de celliilose transparentes ou translucides et de cuirs blancs ou colores en teintes claires, etc. Le nouveau compose est egalement utilisable pour des vernis, des revete- ments plastiques et des objets plastiques colo- res. Il presente une affinite pour et une com- patibilit6 particulierement bonnes avee les resines aminoplastes. The use of the product obtained according to the invention is not limited to the treatment of a particular fiber; on the contrary, it is suitable for processing animal fibers as well as vegetable fibers and synthetic fibers, such as, for example, fibers of artificial silk, nylon, etc. The use of this product is furthermore not limited to the treatment of textile materials. It can also be used with advantage in the manufacture of paper and felt products, transparent or translucent sheets or films of cellulose and white or colored leathers in light shades, etc. The new compound can also be used for varnishes, plastic coatings and colored plastic objects. It has a particularly good affinity for and compatibility with aminoplast resins.

L'exemple suivant montre comment an peut realiser 1'invention. Les Parties sont in- diquees en poids. The following example shows how an can carry out the invention. Parts are given by weight.

Exemple: Du Chlorure de 2,4-dimethoxybenzoyle, obtenu en laissant reagir un melange de 10,9 Parties d'acide 2,4-dimethoxybenzoiqiie et de 9 Parties de Chlorure de thionyle ä la tempe- rature ambiante, 1'exces de Chlorure de thio- nyle etant ensuite chasse, est ajoute ä une Suspension de 4,4 Parties d'acide 5,5'-dichloro- 4,4'-diaminostilbene-2,2'-disiilfonique dans 147 Parties de pyridine. Le melange est ehauffe sous reflux jusqu'ä ce que 1'acylation soit ter- minee. 0n verse 1e melange reactionnel dans environ 700 Parties d'eau et an ajoute du ear- bonate de sodium en quantite suffisante pour obtenir une reaction faiblement basique. 0n ajoute 20 Parties de sel, puis ön soumet la solution ä une distillation par entrainement ä la vapeur d'eau afin de chasser la pyridine. Le residu boueux est filtre ä la temperature ambiante, lave avec une solution de sel ä 2 % et seche ä 100 C. Ön obtient un rendement eleve en un produit constituant un solide jaune qui se decompose, sans fusion, ä des temperatilres elevees, et qui est faiblement soluble dans 1'eäu et quelque peu plus soluble dans de l'alcool aqueux et dans de la pyridine aqueuse. Example: 2,4-Dimethoxybenzoyl chloride, obtained by reacting a mixture of 10.9 parts of 2,4-dimethoxybenzoyl acid and 9 parts of thionyl chloride at room temperature, excess chloride of thionyl being then driven off, is added to a suspension of 4.4 parts of 5,5'-dichloro-4,4'-diaminostilbene-2,2'-disilfonic acid in 147 parts of pyridine. The mixture is heated under reflux until the acylation is complete. The reaction mixture is poured into about 700 parts of water and sodium carbonate is added in sufficient quantity to obtain a weakly basic reaction. 20 Parts of salt are added, then the solution is subjected to steam distillation to remove the pyridine. The sludge residue is filtered at room temperature, washed with a 2% salt solution and dried at 100 C. A high yield is obtained of a product constituting a yellow solid which decomposes, without melting, at high temperatures, and which is sparingly soluble in water and somewhat more soluble in aqueous alcohol and in aqueous pyridine.

Ce produit constitue un agent Aclaircis- sant possedant d'excellentes proprietes. Son pouvoir eclaircissant eleve est encore augmente par 1e degre inhabituel de son affinite. Ainsi, par exemple, ä des concentrations de 0,25 %, son pouvoir eelaircissant est superieixr d'envi- ron 50 RTI ID="0002.0275" WI="4" HE="4" LX="1262" LY="807"> % ä celui du deriv e 2,4-dimethoxy- benzoylique de 1'acide 4,4'-diaminostilbene- 2,2'-disulfonique. En outre, il presente une resistance remarquable au blanehiment et ne perl que 18 0/a de son pouvoir eclaircissant dann un bain d'hypoehlorite sous des condi- tions provoquant la destruction de 60 0/a du pouvoir eelaircissant du derive de Pacide diaminostilbene-disulfonique mentionne ci- dessus. This product is a lightening agent with excellent properties. Its high lightening power is further enhanced by the unusual degree of its affinity. Thus, for example, at concentrations of 0.25%, its lightening power is about 50% higher RTI ID="0002.0275" WI="4" HE="4" LX="1262" LY="807 ">% to that of the 2,4-dimethoxy-benzoyl derivative of 4,4'-diaminostilbene-2,2'-disulphonic acid. In addition, it exhibits remarkable resistance to bleaching and only loses 18% of its lightening power in a hypochlorite bath under conditions causing the destruction of 60% of the whitening power of the diaminostilbene-acid derivative. disulfonic mentioned above.

Claims

RE VE, NDIC ATION: Process for the preparation of the disodium salt of the 2,4-dimethoxybenzoyl derivative of 5,5'-dichloro-4,4'-diaminostilbene-2,2'-disulphonic acid, characterized in that 2,4-dimethoxybenzoyl halide is reacted with 5,5'-dichloro-4,4'-diaminostilbene-2,2'-disulfonic acid and the reaction product is treated with a salt sodium to form the disodium salt of the 2,4-dimethoxybenzoyl derivative of said acid. The compound obtained is a yellow solid which decomposes, without fusion, at elevated temperatures and which is slightly soluble in water and slightly more soluble in aqueous alcohol and. aqueous pyridine. SUB-CLAIM: Process according to the claim, characterized in that the reaction is carried out in an inert solvent.