CS269945B1 - Method of naphthoylenbezimidazole's cis-isomer's pigment form preparation - Google Patents

Abstract

The pigment form is prepared by hydrolysis KOC.rl. or NaOC.H, adduct in water * 2 5 2 5 or in water containing polyethylene oxide wax or chlorobenzene polyethylene oxide solution voi «KOC2 ^ íj or NaOC2H ^ addukt» · prepared by heating in ethanol β KOH or NaOH in the presence of a small amount of water.

Description

The present invention provides a process for the preparation of the pigment form of the isomer of naphthylenebenzimidazole, characterized by a brightness and a bright yellow shade of red.

Condensation of 1,4,5 (6-naphthalentetracarbonate with 1,2-diaminobenzene produces a mixed naphthylenebenzylimidazole dye which is used as a vat dye or is divided into a trans cis cis isomer and these isomers are also used as vat dyes or pigmented pigments. In particular, due to their high temperature stability, pigments are especially used in the recent use in the dyeing of polypropylene fibers, and the differential solubility of their KOH adducts prepared by heating the mixed dye in a water, ethanol, and aqueous medium is mostly used to separate the trans and cis isomers. KOH The solid KOH adduct of the trans isomer is separated from the soluble KOH adduct of the cis isomer and processed to give a color or pigment The red pigment forms of the cis isomer are obtained by literature by treating the purified aqueous alcoholic alkaline mother liquor after separation of the KOH adduct trans The isomer and, after distilling off the ethanol, is hydrolysed by p-toluenesulfonic acid, and the pigment is also obtained by treating the alpha modification of cis naphthylenebenzimidazole with a mixture of water, an organic solvent, an alkali metal hydroxide and a surfactant at a temperature between about 25 ° C or more energy-saving. temperature up to 8 ° C, where the alpha modification is also treated with a mixture of water and an organic solvent (dimethylformamide, dlmethylsulfoxide, monoethylene glycol monoethylether, ethanol, acetone, trlchlorobenzene) or 1 alkali metal hydroxide and surfactant and solvent it is either distilled off or the reaction mixture is diluted with water or an aqueous solution of mineral or organic acid. Beta modification of the cis isomer is formed. Beta modification is also obtained by long-grinding alpha modification with NaCl, KCl, CaCl 2, Na 2 SO 4, K 2 SO 4, Na 2 CO 2, K 2 CO 4 or NaOAc and hydrocarbons, halogenated hydrocarbons or ketones. Another method of preparing the pigment form of the beta modification is to hydrolyze the slightly yellowish precipitate of NaOH of cis naphthylenebenzimidazole adduct in water containing a chlorobenzene solution of polyethylene oxide wax (solidification point 9o to 94 ° C, density at 20 ° C, 91 to 0.92).

Thus, in all the examples, the pigment is prepared either by treating the alpha modification, either by grinding in hydrocarbons or ketones in the absence of water, or by other treatments in the presence of water, and / or by pigment hydrolysis of the KOH or NaOH adduct formed in an environment containing predominantly or more water.

The known processes produce alpha or beta modifications of cis naphthoylenebenzimidazole, which form lacquered red paints with a blue tint, staining I polypropylene fiber in the same shade.

It has now been found that a cis-naphthoylenebenzimidazole pigment with a higher yield, a brilliant yellow shade of red, coloring polypropylene fiber, is formed when polyethylene oxide wax or a chlorobenzene solution of polyethylene oxide wax (with a pour point of 38-2 ° C) is present in water or water. densities at 20 ° C of 1.15 to 1.17, commercial name, for example, RV or Apretar P), hydrotreated with KOCl 2 Hg or NaOCl 2 H 2 cis naphtholenebenzimidazole adduct, crystalline orange substance and a yellowish tint resulting from heating cis isomerunaphtoylenebenzimidazole and ethanol containing at most 7% water, preferably by heating with 96% ethanol and solid KOH or NaOH to 65 max. Hydrolysis in water or water containing polyethylene oxide wax or chlorobenzene solution of polyethylene oxide wax is carried out at 2 ° C to 75 ° C.

In contrast to the process in which the NaOH adduct of the cis isomer formed from the aqueous medium from which most of the ethanol was previously distilled is hydrolyzed, the hydrolyzed KOClHg (or NaOClHg) additive compound cis naphtenylene benzimidazole. Preparation of the cis naphthylenebenzimidazole pigment form by KOClHl hydrolysis (or NaOClH 2) additive cis naphthoylenebenzimidazole in water or water containing polyethylene oxide wax or chlorobenzene polyethylene oxide wax solution.

The preparation procedure is further illustrated by examples.

Claims (1)

Example 1: 1 g of dried alpha modification of naphthoylenebenzimidazole, 89 ml of 96% ethanol and 19 g of solid KOH was heated to 65 to 7 ° C with stirring, and stirred at this temperature. After cooling, an orange precipitate was filtered off and sucked off sharply, which was taken up in 2,000 ml of water at 5 ° C, warm. 0.5 g of polyethylene oxide wax trade name RV aptener dissolved in 2 ml of chlorobenzene After stirring the mixture for 3 hours at 7 to 75 ° C, the cooled mixture was filtered, the filter cake washed with ethanol and water. Drying at 8 to 9 ° C yielded 8 g of a pigment staining polypropylene silk with a bright red color with a yellow tint. Example 2, 1 g of the dried cis isomer of naphthoylenebenzimidazole, 90 ml of 96% ethanol and 1 g of solid NaOH was heated to 65-70 ° C with stirring for 6 minutes. After cooling, the slurry was filtered, a sharply aspirated cake of orange-yellow adduct precipitate was partially transferred to a 1-ml of ice-cooled water containing 0.5 g of polyethylene oxide wax trade grade Aperture P dissolved in 2 ml of chlorobenzene, stirred for 15 minutes under cooling and then at normal temperature for 8 hours . After filtration, washing with ethanol and water and drying at 6 to 9 ° C, 8 g of a very bright red pigment with a yellow tint was obtained. Example 3. The KOCl 3 adduct was prepared as in Example 1, and the adduct cake was added in ice-cooled water to 5 ° C in portions containing 0.4 g polyethylene oxide wax. The mixture was stirred at normal temperature for 5 hours, the pigment was filtered off, washed with water and dried at 8 ° C. Example 4. The NaOClHg adduct was prepared as in Example 2. and the adduct cake was added in portions of water. The mixture was stirred at normal temperature for 3 hours. The pigment was filtered off and dried at 80 ° C. OBJECT OF THE INVENTION A process for preparing the cis form of the naphthoylenebenzimidazole cis isomer by preparing KOCgHg or NaOClHg additive cis naphthoylenebenzimidazole compound by heating with ethanol containing at most 7% water, preferably by heating with 96% ethanol and solid KOH or NaOH to 65-7o ° C, which is hydrolysed in water or water containing polyethylene oxide wax or chlorobenzene polyethylene oxide wax solution at 2o to