Epoxidized soybean oil itaconate as well as preparation method and application thereof

A technology of oil itaconate and epoxidized soybeans, which is applied in the direction of carboxylic acid ester preparation, fatty acid esterification, chemical instruments and methods, etc., can solve the problem of low activity of epoxide groups in epoxidized soybean oil, which is difficult to remove Eliminate problems such as acrylic acid and corrosion, and achieve the effects of avoiding the use of petrochemical products, easy implementation and control, and simple preparation process

Active Publication Date: 2016-07-27
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] First, AESO is obtained by the reaction of epoxidized soybean oil and acrylic acid. The acrylic acid used as a raw material is highly irritating and corrosive, which can cause burns to the human body. Its steam and air can form an explosive mixture, which can cause combustion and explosion when exposed to open flames and high heat. Heat, light, moisture, peroxides and iron are easy to self-polymerize and cause explosions, which have high requirements for storage, transportation and use conditions and environments; and because the epoxy group activity of epoxy soybean oi

Method used

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  • Epoxidized soybean oil itaconate as well as preparation method and application thereof
  • Epoxidized soybean oil itaconate as well as preparation method and application thereof
  • Epoxidized soybean oil itaconate as well as preparation method and application thereof

Examples

Experimental program
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Example Embodiment

[0031] Example 1

[0032] 100 parts by mass of epoxy soybean oil, 55 parts by mass of monoethyl itaconate, 4 parts by mass of tetrabutylammonium bromide and 0.5 parts by mass of hydroquinone are mixed uniformly, heated and stirred, and reacted at 110° C. for 2 h. After the reaction is over, the crude reaction product is dissolved with dichloromethane and washed with water. After the solvent and water are removed by vacuum distillation, the final product is obtained. 1 The peak at 5.8-6.3ppm in the HNMR spectrum corresponds to the H on the double bond of the itaconic acid structure, and other peaks are consistent with the H proton shift in the epoxy soybean oil itaconate structure, which proves that the product obtained is Epoxidized soybean oil itaconate, the structural formula is as follows:

[0033]

Example Embodiment

[0034] Example 2

[0035] Mix 100 parts by mass of epoxy soybean oil, 70 parts by mass of itaconic acid monomethyl ester, 5 parts by mass of cetyltrimethyl ammonium chloride and 0.5 parts by mass of 2,5-di-tert-butyl hydroquinone. Then, it was heated and stirred, and reacted at 150°C for 0.5h. After the reaction is over, the crude reaction product is dissolved with dichloromethane and washed with water. After the solvent and water are removed by vacuum distillation, the final product is obtained. 1 The peak at 5.8-6.3ppm in the HNMR spectrum corresponds to the H on the double bond of the itaconic acid structure, and other peaks are consistent with the H proton shift in the epoxy soybean oil itaconate structure, which proves that the product obtained is Epoxidized soybean oil itaconate, the structural formula is as follows:

[0036]

Example Embodiment

[0037] Example 3

[0038] 100 parts by mass of epoxy soybean oil, 10 parts by mass of itaconic acid, 40 parts by mass of monobutyl itaconate, 8 parts by mass of triphenylphosphine, 0.1 parts by mass of p-hydroxyanisole, 0.1 parts by mass of 2-tert-butyl After the hydroquinone is evenly mixed, it is heated and stirred, and reacted at 30°C for 5 hours. After the reaction is over, the crude reaction product is dissolved in dichloromethane and washed with water. After the solvent and water are removed by vacuum distillation, the final product is obtained. The 1HNMR spectrum of the product shows a peak at 5.8-6.3ppm corresponding to the structure of itaconic acid The H on the double bond and other peaks are consistent with the H proton shift in the structure of epoxy soybean oil itaconate, which proves that the obtained product is epoxy soybean oil itaconate, the structural formula is as follows:

[0039]

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Abstract

The invention discloses epoxidized soybean oil itaconate with the structural formula I shown in the specification and also discloses a preparation method of the epoxidized soybean oil itaconate and an application of the epoxidized soybean oil itaconate in a coating, further in an ultraviolet curing coating. Itaconic acid which has rich biological sources and is cheap and environment-friendly replaces acrylic acid, photocuring active double bonds are introduced into an epoxidized soybean oil molecule structure, and the toxicity problem caused by AESO residual acrylic acid is solved; besides, more polar carboxyl and ester bonds are introduced, the interaction of soybean oil based oligomers with other components in the coating and base materials can be increased, and the overall performance of the coating is improved. In the formula I shown in the specification, R1, R2, R3 and R4 are independently selected from a formula II shown in the specification, and n represents 0, 1, 2, 3 or 4.

Description

technical field [0001] The invention relates to the field of bio-based polymer materials, in particular to an epoxy soybean oil itaconate and its preparation method and application. Background technique [0002] UV-curable coatings have many advantages such as fast curing speed (in seconds), environmental protection and energy saving, excellent coating performance, no need for high temperature, and can be used for heat-sensitive substrates such as plastics, paper and wood, so they are developing rapidly. Combining bio-renewable raw materials with UV-curable coating technology is a "green+green" solution to solve the environmental problems currently faced by the coatings industry. [0003] At present, the bio-based raw materials combined with UV-curable coating technology are mainly limited to vegetable oil-based oligomers. Among them, soybean oil is abundant in sources all over the world, cheap, non-toxic and environmentally friendly, and has good low-temperature flexibility...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/675C11C3/08C09D4/00
CPCC07C67/08C07C69/675C09D4/00C11C3/08C08F212/08C08F222/1006
Inventor 江艳华马松琪李鹏刘小青朱锦
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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