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Low-viscosity turpentine-based monoterpene vinyl ester resin monomer and preparation method and application thereof

A technology of vinyl ester resin and monoterpene-based carboxylic acid, which is applied in the field of preparation of bio-based low-viscosity turpentine-based monoterpene vinyl ester resin, can solve the problem of limiting wide application, environmental pollution, yellowing and chalking of cured products and other problems, to achieve the effect of ensuring strength and durability, saving conventional energy, and easing reaction conditions

Inactive Publication Date: 2012-12-19
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the conventional unsaturated polyester resin diluent monomer styrene in the market contains a large number of rigid benzene ring structures, and its cured product is very brittle. The cured product generally has the disadvantages of poor toughness and low impact resistance. It is easy to break due to uniform or external force; in addition, the conventional diluent monomer styrene contains a large number of benzene ring structures, which is not resistant to ultraviolet rays and has poor outdoor weather resistance. Under the photooxidation of outdoor light and atmosphere, unsaturated polyester resin cured products are prone to yellowing and chalking
At present, almost all other conventional light-curing coating monomers use petrochemical resources such as petroleum and coal as raw materials. The problem of environmental pollution is serious, which will seriously hinder the development of environmental protection.
In order to solve the weather resistance, raw materials containing alicyclic structure in the molecule can be used in industrial applications to prepare diluent monomers or unsaturated polyester resins. The alicyclic structure can endow the material with excellent water resistance, corrosion resistance and mechanical properties, but this Resin-like price is relatively expensive, which limits its wide application

Method used

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  • Low-viscosity turpentine-based monoterpene vinyl ester resin monomer and preparation method and application thereof
  • Low-viscosity turpentine-based monoterpene vinyl ester resin monomer and preparation method and application thereof
  • Low-viscosity turpentine-based monoterpene vinyl ester resin monomer and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Under a nitrogen atmosphere, put a certain amount of acrylic acid in a reaction flask, stir and heat to control the temperature to 45°C, then add α-phellandrene monomer dropwise at a molar ratio of 1.2:1 to acrylic acid, and then add the total mass 0.25% of the catalyst diaryl prolinol silicon ether, heated to 60 ° C, reacted for 2 hours, and used a rotary evaporator to remove excess unreacted α-phellandrene monomer to obtain monoterpene-based carboxylic acid; under nitrogen atmosphere, Add the solvent benzene with a mass ratio of 1.5:1 to the prepared monoterpene-based carboxylic acid, stir and heat to control the temperature to 60°C, add dropwise methacrylic acid shrinkage at a molar ratio of 1.0:1 to the monoterpene-based carboxylic acid Glycerides; then add 0.10% of total mass of hydroquinone, add 0.50% of total mass of benzyltrimethylammonium chloride, then raise the temperature to 80°C, and reflux for 2 h to obtain the intermediate product monoterpene unsaturated ...

Embodiment 2

[0049] Under a nitrogen atmosphere, put a certain amount of maleic anhydride in a reaction flask, stir and heat to control the temperature to 60°C, and then add α-pine oil dropwise at a molar ratio of 1.2:1 to maleic anhydride Then add 2.5% catalyst triethylamine of the total mass, raise the temperature to 150°C, react for 6h, use rotary evaporator to remove excess unreacted α-phellandrene monomer to obtain monoterpene-based carboxylic anhydride; Under the atmosphere, add the solvent carbon tetrachloride with a mass ratio of 2.5:1 to the prepared monoterpene-based carboxylic anhydride, stir and heat to control the temperature to 80°C, and the molar ratio to the monoterpene-based carboxylic anhydride is 2.2:1 Add glycidyl methacrylate dropwise; then add 0.25% of the total mass inhibitor 2,5-di-tert-butylhydroquinone, add 2.5% of the total mass catalyst N,N-dimethylbenzylamine, Then raise the temperature to 120°C and reflux for 4 hours to obtain the intermediate product monoterp...

Embodiment 3

[0051] Under a nitrogen atmosphere, put a certain amount of cinnamic acid in a reaction flask, stir and heat to control the temperature to 50°C, then add β-phellandrene monomer dropwise at a molar ratio of 1.05:1 to cinnamic acid, and then add The catalyst titanium tetrachloride with a total mass of 0.5% was heated up to 75° C., reacted for 2 hours, and the excess unreacted β-phellandrene monomer was removed by a rotary evaporator to obtain a monoterpene-based carboxylic acid; under a nitrogen atmosphere, the prepared Add solvent dichloromethane with a mass ratio of 2:1 to the obtained monoterpene-based carboxylic acid, stir, heat and control the temperature to 70°C, and add methyl Glycidyl acrylate; Then add 0.15% of total mass inhibitor 2-tert-butylhydroquinone, add 0.75% of total mass catalyst triethylbenzyl ammonium chloride, then be warming up to 100°C, backflow for 3 h, the intermediate product monoterpene-based unsaturated diglyceride was obtained; under a nitrogen atmo...

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Abstract

The invention discloses a low-viscosity turpentine-based monoterpene vinyl ester resin monomer and a preparation method and application thereof. The preparation method comprises the following steps of: under an oxygen-free environment, enabling turpentine monoterpene monomers to react with unsaturated carboxylic acid or anhydride to obtain monoterpene carboxylic acid or anhydride, then enabling the obtained monoterpene carboxylic acid or anhydride to react with unsaturated carboxylic acid glycidyl ester to obtain monoterpene unsaturated diglyceride, adding modifier for modification, and decolorizing by using activated carbon to obtain the turpentine-based monoterpene vinyl ester resin monomer, wherein the viscosity of the turpentine-based monoterpene vinyl ester resin monomer is 90-130mPa.s, the iodine value is 120-180 and the chromaticity through an iron-cobalt colorimetric method is 4-8. The turpentine-based monoterpene vinyl ester resin monomer prepared by adopting the preparation method has the advantages of low viscosity, low volatility, no toxicity, environmental friendliness and the like, and can be used as thinner of conventional unsaturated polyester resin; and cured resin has the advantages of good toughness, corrosion resistance, weather resistance and high product stability.

Description

[0001] technical field [0002] The invention belongs to the field of unsaturated resins, in particular to a preparation method of bio-based low-viscosity turpentine-based monoterpene vinyl ester resin. Background technique [0003] Unsaturated polyester resin is generally a linear polymer compound with ester bonds and unsaturated double bonds formed by polycondensation of unsaturated dibasic acid diols or saturated dibasic acid diols. Usually after the polyesterification polycondensation reaction, a certain amount of vinyl monomer is added as a diluent to form a viscous liquid. Such a polymer solution is called an unsaturated polyester resin. Unsaturated polyester resin has been widely used in petrochemical, metallurgy, papermaking, electroplating, chlor-alkali, medicine, food, construction and other industries. [0004] At present, the conventional unsaturated polyester resin diluent monomer styrene in the market contains a large number of rigid benzene ring structures, a...

Claims

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Application Information

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IPC IPC(8): C07C67/26C07C69/608C07C69/618C07C69/587C08F283/01
Inventor 夏建陵李守海李梅黄坤汪梅杨小华张燕
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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