Preparation method of orange oil based unsaturated resin monomer

A resin monomer, unsaturated technology, applied in the field of preparation of unsaturated resin monomer, can solve the problems of poor weather resistance, high content of toxic components, poor toughness, etc., to improve comprehensive performance, good product stability, and improve poor toughness. Effect

Inactive Publication Date: 2013-11-13
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] In order to improve the shortcomings of poor toughness, poor weather resistance and high content of toxic components in traditional unsaturated resins, the invention provides a method for synthesizing a novel orange oil-based unsaturated resin monomer, using orange essential oil as a raw material, first through Unsaturated carboxylic acid or acid anhydride undergoes D-A reaction and then converted into sodium salt, then reacts with chloropropene to obtain orange oil-based unsaturated resin monomer

Method used

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  • Preparation method of orange oil based unsaturated resin monomer

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Experimental program
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Effect test

Embodiment 1

[0032] Add a certain mass of maleic anhydride into the reactor, raise the temperature to 45°C to dissolve it completely, add orange essential oil dropwise in a ratio of 1:1 to the molar ratio of maleic anhydride, and add Titanium tetrachloride with a mass of 0.25% catalyst was heated to 70°C, reacted for 6 hours, and unreacted orange essential oil, maleic anhydride and a small amount of by-products were removed by vacuum distillation to obtain an intermediate product orange oil-based maleic anhydride. Dissolve the obtained orange oil-based maleic anhydride in water, and then add dropwise an aqueous solution of sodium hydroxide (the amount of sodium hydroxide is equal to the number of moles of carboxyl groups), and continue the reaction for 3 hours after the dropwise addition. After the reaction was completed, the solvent water was distilled off, and vacuum-dried to obtain the sodium salt of orange oil maleic anhydride. The sodium salt of orange oil base maleic anhydride and ch...

Embodiment 2

[0035] Add a certain amount of fumaric anhydride into the reactor, raise the temperature to 60°C to dissolve it completely, add orange essential oil dropwise at a ratio of 1.2:1 to the molar ratio of fumaric anhydride, and add Titanium tetrachloride with a mass of 0.25% catalyst was heated to 150°C, reacted for 4 hours, and unreacted orange essential oil, fumaric anhydride and a small amount of by-products were removed by vacuum distillation to obtain an intermediate product orange oil-based fumaric anhydride. Dissolve the obtained orange oil-based fumaric anhydride in water, and then add dropwise an aqueous solution of sodium hydroxide (the amount of sodium hydroxide is equal to the number of moles of carboxyl groups), and continue the reaction for 1 hour after the dropwise addition. After the reaction was completed, the solvent water was distilled off and vacuum-dried to obtain the sodium salt of orange oil fumaric anhydride. The sodium salt of orange oil-based fumaric anhyd...

Embodiment 3

[0038]Add a certain mass of crotonic acid into the reactor, raise the temperature to 55°C to dissolve it completely, add orange essential oil dropwise in a ratio of 1.1:1 to the molar ratio of crotonic acid, and add 0.5% of the total mass of the reactants Catalyst butadiene amine, heat up to 90°C, react for 5 hours, and distill off unreacted orange essential oil, crotonic acid and a small amount of by-products under reduced pressure to obtain the intermediate product orange oleyl crotonic acid. Dissolve the obtained orange oleyl crotonic acid in water, and then add dropwise an aqueous solution of sodium hydroxide (the amount of sodium hydroxide is equal to the number of moles of carboxyl groups), and continue the reaction for 2 hours after the dropwise addition. After the reaction was completed, the solvent ethanol was distilled off, and vacuum-dried to obtain the sodium salt of orange oil crotonic acid. The sodium salt of orange oleyl crotonate and chloropropene are dissolved...

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Abstract

The invention discloses a preparation method of orange oil based unsaturated resin monomer. The preparation method comprises the following steps of: reacting a certain amount of orange essential oil with unsaturated carboxylic acid or acid anhydride to prepare orange oil based unsaturated carboxylic acid or acid anhydride; and converting the prepared orange oil based unsaturated carboxylic acid or acid anhydride into salt, and reacting the salt with chloropropene to synthesize the orange oil based unsaturated resin monomer. The orange oil based unsaturated resin monomer which is prepared from the preparation method disclosed by the invention is applied to the unsaturated resin field, and can be used for preparing the corresponding products and materials by ultraviolet curing and heating curing after being mixed with other unsaturated resin monomers in a certain proportion. The unsaturated resin monomer which is prepared by using the orange essential oil as the base body material has low viscosity (500mPa.s-1000mPa.s), a high iodine value (200-270) and the potential of replacing normal non-environment-friendly diluent styrene, and therefore, the product is expected to improve the defect that the conventional unsaturated resin has poor toughness and weather resistance. Meanwhile, the comprehensive performances of the unsaturated resin copolymerized material are improved.

Description

[0001] technical field [0002] The present invention relates to a kind of preparation method of unsaturated resin monomer, mainly relates to prepare orange oil base unsaturated carboxylic acid (anhydride) by D-A reaction, then utilize sodium hydroxide and gained orange oil base unsaturated carboxylic acid (anhydride) ) reaction to prepare orange oil-based unsaturated carboxylic acid sodium salt, and finally react with allyl chloride to prepare orange oil-based unsaturated resin monomer method. [0003] Background technique [0004] Unsaturated resins generally refer to a class of resins containing unsaturated double bonds in their molecular structure, such as unsaturated polyester resins, vinyl ester resins, etc. are common unsaturated resins. The raw materials for synthesizing unsaturated resins generally include unsaturated dibasic acids, diols, bisphenol A, and vinyl monomers containing carbonyl groups. The synthesis methods of its monomers generally include addition, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C11C3/00
Inventor 夏建陵杨雪娟李守海黄坤李梅唐小东杨小华张燕
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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