SU1694573A1 - N,nъ-bis(3,5-ditretbutyl-4-oxybenzyl)maleindiamide as polypropylene stabilizer - Google Patents

Abstract

This invention relates to amides of unsaturated carboxylic acids, in particular, N.N1-bis-3,5-di-tert-butyl-4-hydroxybenzyl-maleindiamide, which can be used as a polypropylene stabilizer. The goal is to create a new, more effective stabilizer of the specified class. Synthesis is carried out by the reaction of 2,6-di-tert-butyl-4-dimethylaminomethylphenol maleic acid in the presence of p-toluenesulfonic acid in benzene at boiling. Yield 98.6%; m.p. 171.0-171.2 ° C; Gross F la Sz4N5O№Ol. The new compound is 5 times more effective in NS, 5-di-tert-butyl-4-hydroxybenzyl acrylamide. 1 tab.

Description

cl

with

The invention relates to a novel chemical compound, namely, N.N1-bis (3,5-di-tert-butyl-4-hydroxybenzyl) methyl indiamide, which can be used as a stabilizer for polymeric materials, in particular polypropylene.

The purpose of the invention is to search in the range of amides of unsaturated carboxylic acids with di-tert-butyloxybenzyl substituents of a new compound, which is a more effective stabilizer of polypropylene.

Example 1. In a reactor equipped with a stirrer, a thermometer, a Dean-Stark nozzle, a reflux condenser, a heating bath, 26.2 g (0.2 mol) of 2.6-di-tert-butyl-4-dimethylaminomethylphenol are charged. 34.8 g (0.3 mol) of maleic acid, 180 ml of benzene and 1.3 g of p-toluenesulfonic acid. The contents of the reactor are heated to boiling and stirred for 2-2.5 hours, the theoretical amount of reaction water (3.5 ml) is collected in a Dean-Stark trap. At the end of the reaction, the mass is neutralized with ammonia, washed with water and the organic layer is separated from the aqueous. White crystals of N, bis (3,5-di-tert-butyl-4-hydroxybenzyl) maleidiamide precipitate out of the organic layer. Dry weight 53.2 g (98.6% otteor.), So pl. 171.0-171.2 ° C.

Found,%: C 74.6; 9.0; N 4.9. M 550 (mass spectroscopic)

C34H50N204

Calculated. %: C, 74.18; H 9.09; N 5.09; M 550

IR spectrum (1% solution in CCU), cm-1: 3600 (OH-free). 1700 () 840 (). 3300 (-NH).

UV spectrum (in alcohol), Z max nm: 275,280.

oh che

СП JV VI CJ

EXAMPLE 2: The stability of polypropylene protected by a new stabilizer was evaluated by the induction period g oxidation under standard test conditions (oxygen pressure 250 mm Hg, temperature 114 ° C, initiator — cumyl peroxide, concentration stabilizer 1 , 4-U3 mol / kg polypropylene). For comparison, the stability of polypropylene protected by M- (3,5-di-tert-butyl-4-hydroxybenzyl) acrylamide and a known stabilizer of the class Bisphenols NG-2246 was determined.

The results are shown in the table.

The proposed stabilizer is more than twice as effective as (3,5-di-tert-butyl-4-hydroxybenzyl) acrylamide and is not inferior to the most effective stabilizer of the bisphenol class NG-2246. 5F o rumlula and z o bre tem

M, S - Bis (3,5-di-tert-butyl-4-hydroxybenzyl) maleindiamide of formula

onon

10 (CHjbC ClCHjJj (CHjbC G C (CH3) 3

SN RSHOO SNSNK g

15

as a polypropylene stabilizer.

Claims (1)

5 FORMULA AND PORTRAIT Ν, Ν '-Bis (3,5-di-tert-butyl-4-hydroxybenzyl) maleindiamide of the formula he he C (CH ₃ ) s (CH ₃ ) ₃ C Ϊ C (CH ₃ ) ₃ W CH jNHCOCH ^ CHCONHCH _g 15 as a stabilizer for polypropylene. Stabilizer The induction period, g, min Without stabilizer 20 The compound of example 1 230 M- (3,5-Ditret-butyl-4-hydroxybenzyl) acryl- MFA 100-105 NG-2246 200