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Method for synthesizing allyl alcohol polyethenoxy ether metacrylic acid ester

A technology of allyl alcohol polyoxyethylene ether methacrylate and allyl alcohol polyoxyethylene ether, which is applied in the field of synthesis of ester compounds in organic chemistry, to achieve the effects of shortened reaction time, mild conditions, and safe and easy operation

Inactive Publication Date: 2009-08-05
ZHEJIANG HUANGMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Allyl alcohol polyoxyethylene ether methacrylate is a bifunctional monomer containing two polymerizable double bonds, and the polymerization performance of the α-position double bond is much better than that of allyl, regardless of free radical polymerization or anionic polymerization. At the same time, it not only has lipophilic groups (alkyl groups) and hydrophilic groups (polyoxyethylene groups), but also the molecular polarity increases or decreases with the number of ethylene oxide groups in the molecule, and the HLB value can be adjusted as needed , so it has a wide range of uses, suitable for silicone oil modification, and optical lenses, reinforced plastics, adhesives, coatings, rubber, ink crosslinking agents and other fields. At present, allyl alcohol polyoxyethylene ether methacrylate Synthetic process rarely reported

Method used

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  • Method for synthesizing allyl alcohol polyethenoxy ether metacrylic acid ester

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Embodiment 1

[0016] Embodiment 1: Add allyl alcohol polyoxyethylene ether 174.2g (polymerization degree is 5), methacrylic acid 72.6g, gac solid 13.5g of phosphotungstic acid, 0.25g of hydroquinone as a polymerization inhibitor, 201g of water-carrying agent (volume ratio of toluene:cyclohexane=35:65), the temperature is raised to 100-105°C under stirring, and nitrogen gas is introduced. React for 5.5 hours, when the water-carrying agent does not react and produce water, it is the end of the reaction. Turn off the nitrogen, cool down to 60-70°C, filter and remove the catalyst phosphotungstic acid (recovered for reuse), and then add 0.49g of diatomaceous earth to the filtrate , stirred for about 30 minutes, filtered, and the solvent was distilled off under reduced pressure to obtain allyl alcohol polyoxyethylene ether methacrylate, the acid value was less than 0.5mgKOH / g, and the esterification rate was 98.5%.

Embodiment 2

[0017] Embodiment 2: Add allyl alcohol polyoxyethylene ether 177.6g (polymerization degree is 9), methacrylic acid 48.2g, gac solid 18.0g of phosphotungstic acid, 0.18g of polymerization inhibitor phenothiazine, 225.8g of water-carrying agent (volume ratio of toluene: cyclohexane = 45:55), the temperature is raised to 110-115°C under stirring, and nitrogen gas is introduced. React for 6.0 hours, when the water-carrying agent does not react and generate water, it is the end of the reaction. Turn off the nitrogen, lower the temperature to 60-70°C, filter and remove the catalyst phosphotungstic acid (recovered for reuse), and then add 0.68g of diatomaceous earth to the filtrate , stirred for about 30 minutes, filtered, and the solvent was distilled off under reduced pressure to obtain allyl alcohol polyoxyethylene ether methacrylate, the acid value was less than 0.5mgKOH / g, and the esterification rate was 98.0%.

[0018] In the above-mentioned embodiment, reaction equation is:

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Abstract

The invention provides a method for synthesizing an allyl alcohol polyethenoxy ether metacrylic acid ester, and belongs to the technical field of synthesizing ester compounds in the organic chemistry. The method comprises that: an allyl alcohol polyethenoxy ether and a methacrylic acid are used as raw materials, a phosphotungstic acid immobilized on active carbon is used as a catalyst, phenothiazine or hydroquinone or a mixture of the phenothiazine and the hydroquinone is used as a polymerization inhibitor, and in the presence of a water-carrying agent and under the condition of continuously filling with nitrogen, the esterification reaction is carried out, after the reaction, the obtained products are refined to obtain the allyl alcohol polyethenoxy ether metacrylic acid ester; and the degree of polymerization of a chain segment of the allyl alcohol polyethenoxy ether is between 1 and 10, and a mol ratio of the allyl alcohol polyethenoxy ether to the methacrylic acid is 1.0:1.0-1.5. According to test comparisons, the method has the advantages of reasonable use of the phosphotungstic acid immobilized on active carbon with good catalytic activity and stability as the catalyst, more advanced and reasonable process, mild reaction conditions and safe and easy operation, and solves the problem of the equipment corrosion.

Description

technical field [0001] The invention relates to a synthesis method of allyl alcohol polyoxyethylene ether methacrylate, which belongs to the technical field of synthesis of ester compounds in organic chemistry. Background technique [0002] Allyl alcohol polyoxyethylene ether methacrylate is a bifunctional monomer containing two polymerizable double bonds, and the polymerization performance of the α-position double bond is much better than that of allyl, regardless of free radical polymerization or anionic polymerization. At the same time, it not only has lipophilic groups (alkyl groups) and hydrophilic groups (polyoxyethylene groups), but also the molecular polarity increases or decreases with the number of ethylene oxide groups in the molecule, and the HLB value can be adjusted as needed , so it has a wide range of uses, suitable for silicone oil modification, and optical lenses, reinforced plastics, adhesives, coatings, rubber, ink crosslinking agents and other fields. At...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C07C67/08B01J27/19
Inventor 王伟松王新荣孟照平王胜利朱红军
Owner ZHEJIANG HUANGMA TECH
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