Fumarate derivative, method for producing the same

A technology of fumarate and derivatives, which is applied in the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, and can solve the problems of no cross-linking points and low surface hardness of cured products

Inactive Publication Date: 2002-12-18
RESONAC HOLDINGS CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, these polymerizable compounds only have two polymerizable groups at the end and one polymerizable group in the chain, and still do not have enough cross-linking points
[0015] The object of the present invention is to provide novel fumaric acid ester derivatives, which can overcome the problems in conventional radically polymerizable compounds, such as curing inhibition by oxygen or low surface hardness of cured products during curing, and which have sufficient multiple cross-links

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0240] In a 1-liter volumetric flask equipped with a distillation device, 312 grams of bis(2-allyloxyethyl) maleate, 135 grams of ethylene oxide 2-mole adduct of bisphenol A, 0.4 gram of dibutyltin oxide, and 0.12 gram of tetrakis[methylene-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate] methane (trade name "IRGANOX 1010", manufactured by Chiba Specialty Chemicals). While gradually reducing the pressure in the reaction system, the mixture was heated at 160° C., and ethylene glycol monoallyl ether produced as a by-product was distilled off. Finally, the pressure was reduced to about 400 Pa and almost the theoretical amount of ethylene glycol monoallyl ether was distilled off.

[0241] After cooling the reaction solution to room temperature, 385 g of product were obtained. measure the product 1 H-NMR ( 1 H-NMR) and IR (infrared spectroscopy), it was determined that this product was the condensation product of bis(2-allyloxyethyl) maleate and the ethylene oxide 2-mole adduc...

Embodiment 3

[0268] In the glass flask that stirring device, thermometer, condenser and the distillation acceptor with piston are equipped with in 500 milliliters of volumes, the single-2-allyloxyethyl fumarate of 154 grams embodiment 2 is charged into, 21.8 gram of pentaerythritol, 200 milliliters of benzene and 0.25 grams of p-toluenesulfonic acid. The mixture was heated with stirring in an oil bath, the reaction temperature was raised to 80°C, and water produced as a by-product as the reaction proceeded was distilled off while the reaction was continued. When the distilled-off amount of water reached the theoretical value, the reaction was terminated, and the reaction liquid was cooled. Transfer the reaction solution to a separatory funnel, add 300 ml of benzene, and separate with 10% aqueous sodium carbonate solution and water. Thereafter, the resulting solution was concentrated under reduced pressure to obtain 120 g of product.

[0269] 1 H-NMR, FT-IR, GC and GPC, determine that th...

Embodiment 4

[0273] In the glass flask that stirring device, thermometer, condenser and the distillation acceptor with piston are equipped with in 500 milliliters of volumes, the mono-2-allyloxyethyl fumarate of 152 grams embodiment 2 is charged into, 21.5 gram of trimethylolpropane, 200 ml of benzene and 0.25 gram of p-toluenesulfonic acid. The mixture was heated with stirring in an oil bath, the reaction temperature was raised to 80°C, and water produced as a by-product as the reaction proceeded was distilled off while the reaction was continued. When the distilled-off amount of water reached the theoretical value, the reaction was terminated, and the reaction liquid was cooled. Transfer the reaction solution to a separatory funnel, add 300 ml of benzene, and separate with 10% aqueous sodium carbonate solution and water. Thereafter, the resulting solution was concentrated under reduced pressure to obtain 118 g of product.

[0274] Measurement 1H-NMR, FT-IR, GC and GPC, confirm that th...

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Abstract

The present invention provides a polymerizable composition having excellent curing properties and surface hardness, and a cured product made therefrom. Also provided are novel fumarate derivatives containing not less than two fumarate groups in the molecule and capable of ensuring a high degree of copolymerization with terminal alkenyloxy groups, as well as the production method of the derivatives and the derivatives containing the derivatives. polymerizable compositions of materials, and cured products made therefrom.

Description

[0001] see application [0002] This application is an application pursuant to 35 U.S.C § 111(a) having the benefit of provisional application 60 / 246,58935, filed November 8, 2000, under 35 U.S.C. § 111(b). field of invention [0003] The present invention relates to novel fumarate derivatives with excellent free radical polymerization, which can be made into polymers by light or heating, and can be used as cross-linking agents for various polymers, especially for In the field of curing, such as paints, coatings, adhesive and sealing materials, it also relates to the production process of this derivative, the polymerizable composition containing this derivative, and the cured product made from it. Background of the invention [0004] Hitherto, polyfunctional compounds containing double bonds have been used in many applications such as raw materials for polymerizable compositions and the like. [0005] These polymerizable compositions are mainly cured by free radical polymer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/60C08G63/52C08G63/547C08G63/553
CPCC07C69/60C08G63/52C08G63/547C08G63/553
Inventor 甲斐和史太田启介门脇靖内田博
Owner RESONAC HOLDINGS CORPORATION
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