The method of obtaining the oligomeric dyes

 

(57) Abstract:

Purpose: the oligomeric dyes, soluble in polymers intended for coloring thermoplastic materials such as polyolefins, polyvinyl chloride. The inventive method of obtaining oligomeric dyes is that epoxyether based on epoxygenase resin with a molecular mass of 1000-4500 g/mol and a monobasic carboxylic acid is subjected to interaction with the metal complex azo dye composition 1:2 containing at least two phenylsulfinyl groups. The obtained dye are resistant to migration. table 2.

The invention relates to the field of organic dyes, in particular to a method of obtaining polimerisation dyes containing in the molecule fragments of the polymer, i.e., the method of production of oligomeric dyes.

A method of obtaining oligomeric dyes by reacting the epoxy compounds with dyes containing reactive groups [1]

The lack of oligomeric dyes obtained by the method described in the prototype, is that for some thermoplastics, there is increased migration oligomeric dyes from GCI polyvinyl chloride.

The invention increases the resistance of the oligomeric dyes migration of the colored polymers.

The study of the properties of the oligomeric dyes showed that the migration stability of these dyes are in particular polymers (PVC and polypropylene) depends on the functionality of the original organic dyes. The most resistant to migration are oligomeric dyes derived from organic dyes with two (or more) of carboxy - and/or sulfa groups.

Such bifunctional compounds can be obtained for almost all the major classes of organic dyes (antrahinonovye, azo dyes, microcrystal and others).

Examples 1-4 of table 1 confirm their high migration resistance. A certain difficulty of obtaining the original polyfunctional Monomeric dyes is that you need an individual solution for each specific dye. In addition, the introduction of two such reactive groups as phenylalanine complicated by the presence of monosubstituted dye that increases the probability of migration.

We have shown that the best way to obtain oligomeric dyes avlyasota 1:2 and the structure I, II, III, obtained by the same type of scheme that allows to obtain more affordable way non-migrating oligomeric dyes full color.

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where A NO2, SO2NHPh, H; B NO2, Cl, SO2NHPh, H; C D SO2NHPh, H; M is Cr, Co; Y NH3R1, NH2R1R2, NR1R2R3, NR1R2R3R4; R1R2R3R4CnH2n+1where n for R1R24-18, for R34-8, for R41, 2.

In such symmetric dyes always contains at least two groups (phenylalanine), which can be "set" epoxy fragments.

A necessary condition for the successful use of such dyes in the synthesis of oligomeric dyes is the introduction in their molecule fatty amines as counterions (Y). In this embodiment, the metal complex soluble in the original epoxyamine that ensures the completeness of the "binder".

Obtained on the basis of metal complexes of azo dyes of the oligomeric dyes have very high resistance to migration not only in polyethylene and polypropylene, but in the soft TOLC, which is a great indicator for organic pigments.< the colors) and to ensure a sufficiently high light-fastness (5-7 points on 8-point scale).

Below are examples of original synthesis of metal complexes of azo dyes and model synthesis of the oligomeric dyes based on them.

Example 1. The complex of azo dye-based 5-nitro-2-aminophenol and 1-phenyl-(3'-sulfanilyl)-3-methyl-5-pyrazolone.

1. The diazotization of 5-nitro-2-aminophenol.

Into a flask of 1 l equipped with a stirrer, thermometer, addition funnel is placed a 16.8 g (0.1 mol) of 5-nitro-2-aminophenol, 400 ml of water and 17 ml of 36.5% (0.2 mol) of hydrochloric acid. The reaction mass was stirred for 30 min at room temperature until complete dissolution of 5-nitro-2-aminophenol. Cooled to 0-5oC and diasterous 19 ml of 29.9% solution of sodium nitrite. Excess nitrous acid is removed with a 10% solution of sulfamic acid.

2. Getting monoisocyanates.

In a glass 0.5 l load ratio of 36.9 g (0.11 mol) of 1-phenyl-(3'-sulphonamide)-3-methyl-5-pyrazolone (FMP), 300 ml of water and heated to 40-50oC. At this temperature, poured to 15.4 ml (0.22 mol) of 40% NaOH solution and stirred until complete dissolution of the FMP. Cooled to room temperature and slowly poured it to the solution of diazocompounds, checking the presence of azo - and vasoactivity. Temperature combination 20-25oC, pH 4-5. On obladaut, the precipitate is filtered and washed with water until a colorless filtrate.

3. The complex compounds monoisocyanates.

Into a flask of 1 l equipped with a stirrer and a thermometer download paste monoisocyanates, of 11.45 g (0.05 mol) of chromium acetate, 9,25 g (0.05 mol) of tributylamine and 300 ml of ethylene glycol. The reaction mixture is heated to 110-120oC and incubated with stirring 2-2,5 hours of the End of the reaction is determined by the disappearance of monoisocyanates in the reaction mass by TLC on plate "Silufol" (eluent benzene:acetone 4:1). The reaction mass was diluted 2-fold with water, the precipitation is filtered off, washed with water and dried. The output 46 g (80%).

4. Getting oligomeric dye.

In a flask with stirrer, thermometer and a tube for supplying nitrogen load 1 wt. including aromatic epoxy resin brand e-44 (epoxy number 5,7), heated to melt and contribute with stirring to 0.20 wt. including rosin. Increase the temperature to 180oC and stirred until a residual acid number 1-3 mgKOH/g Determined epoxy number of the formed epoxyether (2,5-3,0).

To the molten mass add powdered dye in the amount of 0.06 wt. hours and triethanolamine in quality the EC reaction is determined by the extinction of the original dye in the reaction mass by TLC on plate "Silufol" (eluent benzene:acetone 10:1).

Characteristics of the synthesized oligomeric based dyes metal complex azo dyes are shown in table 2.

The method of obtaining the oligomeric dyes by reacting epoxysilane with dye containing reactive groups, characterized in that as epoxysilane use epoxyether based on epoxygenase resin with a molecular weight of 1000 to 4500 g/mol and a monobasic carboxylic acid, and dyes metal complex azo dyes of structure 1 2 containing at least two phenylsulfinyl groups.

 

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