The method of obtaining the oligomeric dyes


(57) Abstract:

The invention relates to the production of organic dyes, in particular to methods for oligomeric primarystring dyes. The invention consists in that in the method of obtaining the oligomeric dyes by reacting the epoxy compounds with dyes in the interaction of the introduced aromatic epoxy resin with a molecular weight of 600 to 4500 g/mol. monobasic carboxylic acids as modifiers and colorants containing carboxyl and/or sulfa group at mass ratios of 1:0,06 - 0,20 : 0,08 - and 0.37, respectively. table 1.

The invention relates to the field of organic dyes, in particular to polymerisation dyes containing in the molecule fragments of the polymer, i.e. oligomeric dyes, and the way they are received.

It is known [1] obtaining structural-painted polymer in which the dye is covalently bonded to the polymer by copolymerization or condensation) monomers with dyes containing groups such as vinyl, hydroxy-, amino -, and others, with the formation of the polymer (oligomer) circuits. The main disadvantages of this method of producing painted the amount of the chromophore part dramatically changes the properties of the polymers and, importantly, requires the creation of special dyes for each type of polymers.

We have found that dyes containing oligomeric fragments of a certain structure and chain length, which are capable of dyeing various polymers at the stage of their processing. The main advantage of such oligomeric dyes is that they paint a polymeric material dissolved in a painted substrate, i.e., homogeneous. So when you use them, unlike pigments, eliminating the need for thorough dispersion, the maximum coloring power and conserved physico-mechanical strength of the colored polymers.

Closest to the proposed method according to the essential features is the way in which condensation of biphenol and epichlorohydrin in the presence of 0.1 to 5 wt. to epichlorohydrin 1-(2,3-epoxypropyl)aminoanthraquinone or 1,4-bis(2,3-epoxypropyl) aminoanthraquinone at 40 65oC followed by the addition of aqueous sodium hydroxide solution, heated to 70 to 75oC and further necessary processing (separation, washing, drying) [2]

This method has some significant drawbacks, such as megastud the NGOs disposal or liquidation of wastewater, use as a source of dyes scarce aminoanthraquinones, as not produced in the industry of their N-substituted, containing epoxypropyl group, the introduction of which, firstly, as a rule, reduces the resistance to light and, secondly, leads to the ambiguity of reactions in the primary process, since the interaction occurs not only epoxypropan, but also on the nitrogen atom of the secondary amino group. Last sharply negative impact on the coloristic properties of the dyes and hinders the achievement of the permanency of their color characteristics, which in principle makes it inappropriate to use for this purpose dyes, in which functionally substituted amino group is directly in the chromophore system. And finally, as contrasted with the method aims at obtaining a structurally dyed polymer material in the process of its receipt, and not polimerisation dyes suitable for the dyeing of various polymers.

The objective of the invention is a method of obtaining oligomeric dyes capable of being dissolved, to paint a wide range of industrial polymeric materials (polyolefins, polyvinyl chloride, polystyrene, polyacrylates, and other), Dawa/P> The problem is solved by the fact that epoxysilane face interaction with dyes and colorless compounds modifier containing functional groups, unambiguously and quantitatively reacting with epoxypropane.

As epoxy compounds using industrial epoxy resins of various molecular weights.

As the dyes are dyes of different chemical groups containing carboxyl and/or sulfa group, and a carboxyl group is introduced, as a rule, during the synthesis of the chromophore with the original intermediate products and sulfa group can be entered and ready dyes known methods [2] which considerably broadens the base of suitable dyes and is an additional advantage of this method.

As a modifier can be used compounds containing functional groups which are able to quantitatively react with epoxy compounds, including sulfonamides. It is most convenient to use monocarboxylic acids, aliphatic, aromatic or heterocyclic series.

These components epoxy resin, modifier and dye are injected into the reaction when the mass crmoly.

< / BR>
where: Kpthe residue of an organic dye;

X SO2NY-, -COO-;

Y H, alkyl-, cycloalkyl, aryl-;

M alkyl-, alkenyl-, aryl-, hetaryl-orp;

n 2 12;

m 1 4.

The process proceeds quantitatively, without releasing any by-products.

Example 1. Getting oligomeric dye.

In a flask with stirrer, thermometer, reflux condenser and a tube for supplying nitrogen load 1 wt.h. aromatic epoxy resin brand e-44 (epoxy number 5,7), heated to melt and contribute with stirring to 0.20 wt. including modifier (table, example 1). Raise the temperature to 180oC and stirred until a residual value acid number 1 to 3 mg/g KOH. Is determined by the epoxide number of the formed epoxyether (2,5 3,0).

To the molten mass add powdered dye No. 1 (table) in an amount of 0.21 wt.h. The reaction mass is heated to a temperature of 185oC and stirred under a stream of nitrogen. The end of the reaction is determined by the disappearance of the original dye in the reaction mass by TLC on plate "Silufol" (eluent a mixture of benzene, acetone 10:1).

Characteristics of the synthesized oligomeric dyes are listed in the table is literal, polyacrylate, polyethylene, polyvinyl chloride, fiberglass epoxy resins, rubber, etc.,

The method of obtaining the oligomeric dyes by reacting the epoxy compounds with dyes containing reactive groups, characterized in that during the interaction of the introduced aromatic epoxy resin (mol. m 1000 4500 g/mol, monobasic carboxylic acids as modifiers, and colorants containing carboxyl and/or sulfa group at mass ratios of 1 0,06 0,20 0,08 0,37 respectively.


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