Preparation method of macromole polymerization inhibitor containing phenolic group and azoxy group

A technology of macromolecules and polymerization inhibitors, applied in the field of preparation of macromolecular polymerization inhibitors, can solve the problems such as the preparation method of macromolecular polymerization inhibitors, poor polymerization inhibition effect, short polymerization inhibition time, etc. Application prospect, easy operation, effect of reducing dosage

Active Publication Date: 2012-05-02
JIANGSU LITIAN TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Preparation method of macromole polymerization inhibitor containing phenolic group and azoxy group
  • Preparation method of macromole polymerization inhibitor containing phenolic group and azoxy group
  • Preparation method of macromole polymerization inhibitor containing phenolic group and azoxy group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] 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%.

[0020] 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 1...

Embodiment 2

[0024] 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 MMIn 2 with a yield of 85%.

[0025] 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

[0029] 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 Example 1 of the present invention containing phenolic groups and nitrogen oxygen 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, the obtained product Be TMPTA product 1; Reduce the consumption of small molecular polymerization inhibitor to 1 / 2 in the original process, keep other production conditions unchanged, 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.

[0030] Table 1

[0031] ...

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Abstract

The invention discloses a method for preparing a macromolecular polymerization inhibitor containing phenolic groups and nitroxide groups, which is characterized by dissolving polymethyl acrylate, phenolic compound and nitroxide free radical compound in a solvent according to a mol ratio of 1:x:y, adding 0.5-3.0 wt% of catalyst based on the total mass of reaction mixture, reacting 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, settling the reaction mixture in water, after the settling is dried, and obtaining the macromolecular polymerization inhibitor in which the polyacrylate main chain is connected with the phenolic groups and the nitroxide free radical groups through ester linkage. 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) method of preparation. 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 polymeriz...

Claims

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Application Information

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Patent Type & Authority Patents(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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