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Macromole polymerization inhibitor containing phenolic group and azoxynaphthalene and preparation thereof

A macromolecule and nitrogen-oxyl technology, which is applied in the field of macromolecular polymerization inhibitors containing phenolic groups and nitrogen-oxyl groups and its preparation, can solve the problem of the preparation method of macromolecular polymerization inhibitors that have not yet been seen, poor polymerization inhibition effect, inhibition Short polymerization time and other problems, to achieve a wide range of industrial application prospects, easy to operate, reduce the effect of dosage

Active Publication Date: 2009-08-05
JIANGSU LITIAN TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Regarding small molecular polymerization inhibitors, U.S. Patent No. 3,666,794 proposes to use hydroquinone-phenol-oxygen system for polymerization inhibition of acrylate monomers, but oxygen must be blown in addition, otherwise the polymerization inhibition effect is relatively poor, and the inhibition Polymerization time is short, application is more difficult
Have not yet seen the report of relevant macromolecule inhibitor and preparation method thereof

Method used

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  • Macromole polymerization inhibitor containing phenolic group and azoxynaphthalene and preparation thereof
  • Macromole polymerization inhibitor containing phenolic group and azoxynaphthalene and preparation thereof
  • Macromole polymerization inhibitor containing phenolic group and azoxynaphthalene and preparation thereof

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Experimental program
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Effect test

Embodiment 1

[0029] In a three-neck flask reactor equipped with a stirring device, add 200 g of polymethyl methacrylate with a molecular weight of 2000, 62 g of p-hydroxybenzyl alcohol, 2,2,6,6-tetramethyl-4-hydroxyl-piperidine nitrogen Oxygen radical 17.3g, catalyst Na 2 CO 3 5.6g (2wt%) and solvent N,N-dimethyl-formamide 800mL, stirred and dissolved, heated to 40°C, kept a vacuum of 0.09MPa, reacted until p-hydroxybenzyl alcohol and 2,2 were detected by gas chromatography, The concentration of 6,6-tetramethyl-4-hydroxy-piperidine nitroxide does not change. After the reaction mixture is cooled, it is poured into 2L of water to settle, and the product is collected by filtration and vacuum-dried to obtain a white solid product, named For MMIn 1, its yield was 88%.

[0030] In the infrared spectrum of the resulting product, 1167, 1245cm -1 The stretching vibration absorption peak of the N-O coordination bond is at 2882cm -1 The stretching vibration absorption peak of the C-N bond is at ...

Embodiment 2

[0034] In a three-neck flask reactor equipped with a stirring device, add 200 g of polymethyl methacrylate with a molecular weight of 8000, 62 g of p-hydroxybenzyl alcohol, and 2,2,6,6-tetramethyl-4-hydroxyl-piperidine nitrogen Oxygen radicals 86.5g, catalyst NaOH 5.2g (1.5wt%) and solvent N,N-dimethyl-acetamide 1000mL, stirred and dissolved, heated to 50°C, kept vacuum at 0.08MPa, reacted until detected by gas chromatography The concentration of p-hydroxybenzyl alcohol and 2,2,6,6-tetramethyl-4-hydroxyl-piperidine nitroxide radical does not change any more, after the reaction mixture is cooled, it is poured into 2L of water to settle, and the product is collected by filtration. Drying in vacuo gave a white solid product named MMIn2 with a yield of 85%.

[0035] In the infrared spectrum of the resulting product, 1167, 1245cm -1 The stretching vibration absorption peak of the N-O coordination bond is at 2882cm -1 The stretching vibration absorption peak of the C-N bond is at ...

Embodiment 3

[0039] In the existing trimethylolpropane triacrylate (TMPTA) production process, the SO 4 2- / TiO 2 / La 3+ The solid superacid catalyst is fixed in a fixed-bed reactor, and under the condition of 100±10°C, trimethylolpropane and acrylic acid are directly esterified to obtain TMPTA (original product). Then the macromolecular polymerization inhibitor MMIn1 prepared in the above-mentioned embodiment 1 of the present invention comprising phenolic groups and nitrogen-oxyl groups is loaded and fixed on the same area of ​​the catalyst, keeping other conditions of the original process unchanged, and carrying out continuous production of TMPTA, and the resulting product is TMPTA product 1; reduce the consumption of small molecule polymerization inhibitor to 1 / 2 of the original process, keep other production conditions unchanged, and the resulting product is TMPTA product 2. A comparison of some of their physical properties with the original product is listed in Table 1 below.

[0...

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Abstract

The invention discloses a macromolecular polymerization inhibitor containing phenolic groups and nitroxide groups, and a preparation method thereof. The polymethyl acrylate with polymerization degree of p, the phenolic compound and the nitroxide free radical type compound are dissolved in the solvent according to the mol ratio of 1:x:y, the catalyst with mass being 0.5-3.0wt percent of the total mass of the reaction mixture is added in to react at the temperature of 20-80 DEG C and under the 0.05-0.09MPa until the concentration of the phenolic compound and the nitroxide free radical type compound is not changed, the reaction mixture subsides in water, and the polyacrylate main chain is obtained after the sediment is dried and is connected with the macromolecular polymerization inhibitor containing the phenolic groups and the nitroxide free radical groups through ester linkage; and the method has the advantages that the raw material is easily obtained, the operation is simple and the method is convenient for the industrial production. The prepared product can effectively prevent the acrylate from being polymerized in the production process, reduce the content of the low polymer in the product, reduce the consumption of the total polymerization inhibitor and improve the product quality and has the broad industrial application prospect.

Description

technical field [0001] The invention belongs to the technical field of polymerization inhibitors in polymerization reactions, in particular to macromolecular polymerization inhibitors containing phenolic groups and nitrogen-oxyl groups used to prevent polymerization in the production process of acrylates and methacrylates (hereinafter collectively referred to as acrylates) and its preparation method. Background technique [0002] During the production process of acrylate, due to the carbon-carbon unsaturated double bonds in the structure of acrylic acid and its esters, polymerization reactions are prone to occur, and even gelation and explosion polymerization may occur, resulting in production accidents. Among them, acrylates are more prone to polymerization than acrylic acid, so how to prevent the polymerization of acrylic acid and its esters during the production process is very critical. [0003] Adding a polymerization inhibitor is an effective means to prevent the poly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F120/10C08F8/30C08F8/00
Inventor 缪慧张丽丽刘建华王正美施文芳
Owner JIANGSU LITIAN TECH
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