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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 oil is low, it is different from The ring-opening esterification reaction of acrylic acid is difficult to carry out completely, and the general industrial purification method is difficult to remove the residual acrylic acid, so a certain amount of acrylic acid will remain in the commercialized AESO, which has great harm to human skin, mucous membranes and eyes. harm
[0006] Second, the long aliphatic chain of AESO has low polarity and is too flexible. As a base resin, the coating strength is low, the scratch resistance is poor, and the protection ability to the substrate is weak.

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
Comparison scheme
Effect test

Embodiment 1

[0032] 100 parts by mass of epoxidized soybean oil, 55 parts by mass of monoethyl itaconate, 4 parts by mass of tetrabutylammonium bromide and 0.5 parts by mass of hydroquinone were uniformly mixed, heated and stirred, and reacted at 110° C. for 2 hours. Treat that reaction is finished, with dichloromethane the crude reaction product is dissolved and washed with water, after decompression distillation removes solvent and moisture, obtains final product, the product 1 The peak at 5.8-6.3ppm in the HNMR spectrogram corresponds to the H on the double bond in the itaconic acid structure, and other peaks are consistent with the H proton displacement in the epoxy soybean oil itaconate structure, proving that the obtained product is Epoxy soybean oil itaconate, the structural formula is as follows:

[0033]

Embodiment 2

[0035] Mix 100 parts by mass of epoxidized soybean oil, 70 parts by mass of monomethyl itaconate, 5 parts by mass of cetyltrimethylammonium chloride and 0.5 parts by mass of 2,5-di-tert-butylhydroquinone Afterwards, heat and stir, and react at 150° C. for 0.5 h. Treat that reaction is finished, with dichloromethane with reaction crude product is dissolved and washed with water, after decompression distillation removes solvent and moisture, obtain final product, the product 1 The peak at 5.8-6.3ppm in the HNMR spectrogram corresponds to the H on the double bond in the itaconic acid structure, and other peaks are consistent with the H proton displacement in the epoxy soybean oil itaconate structure, proving that the obtained product is Epoxy soybean oil itaconate, the structural formula is as follows:

[0036]

Embodiment 3

[0038] 100 parts by mass of epoxidized soybean oil, 10 parts by mass of itaconic acid, 40 parts by mass of monobutyl itaconate, 8 parts by mass of triphenylphosphine and 0.1 parts by mass of p-hydroxyanisole, 0.1 parts by mass of 2-tert-butyl After mixing the base hydroquinone evenly, heat and stir, and react at 30°C for 5h. After the reaction is finished, the crude reaction product is dissolved with dichloromethane and washed with water, and the solvent and moisture are removed by distillation under reduced pressure to obtain the final product. The peak at 5.8-6.3 ppm in the 1HNMR spectrogram of this product corresponds to the structure of itaconic acid The H on the double bond, plus other peaks are consistent with the H proton displacement in the epoxy soybean oil itaconate structure, which proves that the obtained product is epoxy soybean oil itaconate, and 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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