RU2667910C1 - Method for preparation of 4-allyl-2-methoxyphenoxyphenylcyclophosphazenes - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: invention relates to a process for the preparation of compounds containing elements of the V or XV group of the periodic system of Mendeleev, namely 4-allyl-2-methoxyphenoxyfluorocyclophosphazenes, which can be used to modify polymer compositions. 4-allyl-2-methoxyphenoxyfluorocyclophosphazenes are prepared by reacting hexafluorocyclotriphosphazene (HFP) [NPF₂]₃ (or mixtures thereof with higher fluorocyclophosphazenes [NPF₂]_n=4-15) with the sodium salt of eugenol in an acetone medium or eugenol in an acetone medium in the presence of potassium carbonate. In this case, half of the fluorine atoms in the HFP or its mixtures with higher fluorophosphazenes are replaced by 4-allyl-2-methoxyphenoxy radicals, containing multiple bonds, capable of copolymerization with vinyl monomers, which prevents the elution of fluorocyclophosphazenes from the resulting materials and imparts antiseptic properties without reducing the mechanical characteristics.

EFFECT: method for the preparation of 4-allyl-2-methoxyphenoxyfluorocyclophosphazenes is proposed.

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Description

The invention relates to a method for producing compounds containing elements of the V or XV group of the periodic table, namely 4-allyl-2-methoxyphenoxy fluorocyclophosphazenes, which can be used to modify polymer compositions. Fluorine-containing compounds are substances that exhibit antibacterial and antifungal activity. However, many of them are not able to chemically bind to the polymer matrix, as a result of which they can be washed out from it under the influence of solvents or impair its mechanical characteristics. For example, alkoxy- and phenoxy-pentafluorocyclotriphosphazenes are known, described in US patents US 3917826 A, US 9406972 B2 and China CN 104558045 A, CN 102702268 A, CN 106518928 A (prototype) in which one fluorine atom in hexafluorocyclotrifosphazene is replaced by an organic radical not containing polymerization groups, respectively, during polymerization together with vinyl monomers, they cannot chemically bind to each other.

The technical task of the invention is to develop a method for producing derivatives of fluorocyclophosphazenes, which contain organic radicals containing polymerization groups, allowing these derivatives to integrate into the polymer matrix during polymerization with vinyl monomers, which simultaneously prevents the fluorocyclophosphazenes from being washed out of the resulting materials and imparts antiseptic properties without reducing mechanical characteristics.

The solution to this problem is achieved by the interaction of hexafluorocyclotrifosphazene (HFP) [NPF ₂ ] ₃ (or its mixtures with higher fluorocyclophosphazenes [NPF ₂ ] _{n = 4-15} ) with the eugenol sodium salt in acetone (a) or eugenol in acetone in the presence of potassium carbonate (b) (Scheme 1). In this case, half of the fluorine atoms in HFP or its mixtures with higher fluorophosphazenes are replaced by 4-allyl-2-methoxyphenoxy radicals (controlled by the corresponding stoichiometric ratio of the reagents used) containing multiple bonds capable of copolymerization. The use of a mixture of fluorocyclophosphazenes greatly simplifies the process by eliminating the time-consuming stage of the separation of HFF and its purification.

The invention is illustrated by the following examples.

Example 1. 0.722 g (0.0029 mol) of HFF dissolved in 10 ml of acetone are loaded into a polypropylene container equipped with a stirrer, and 1.41 g (0.0086 mol) of the eugenol sodium salt is added. The reaction is carried out at room temperature for 50 hours. After completion of the reaction, the product is filtered off and the filtrate is dried to constant weight. The product is a dark brown mass. The yield is 90%.

Example 2. 0.722 g (0.0029 mol) of HFF dissolved in 10 ml of acetone are loaded into a polypropylene container equipped with a stirrer and 1.38 g (0.0084 mol) of eugenol is added in the presence of 1.16 g (0.0084 mol) potassium carbonate. The reaction is carried out at room temperature for 50 hours. After completion of the reaction, the product is filtered off and the filtrate is dried to constant weight. The product is a dark brown mass. The yield is 92%.

Example 3. In the conditions of example 1, but using HFP in a mixture of higher fluorocyclophosphazenes [NPF ₂ ] _{n = 4-15} . The yield is 85%.

Example 4. In the conditions of example 2, but using HFP in a mixture of higher fluorocyclophosphazenes [NPF ₂ ] _{n = 4-15} . The yield is 87%.

Claims (1)

The method of producing 4-allyl-2-methoxyphenoxyfluorocyclophosphazenes by the interaction of hexafluorocyclotriphosphazene (HFP) [NPF ₂ ] ₃ (or its mixtures with higher fluorocyclophosphazenes [NPF ₂ ] _{n = 4-15} ) with the eugenol sodium salt in acetone or eugenol in acetone in the presence of potassium carbonate at room temperature for 50 hours.