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Degradable monomer based on cyclic acetal structure as well as synthesis method and application of degradable monomer

A cyclic acetal and synthesis method technology, applied in recycling technology, organic chemistry, plastic recycling, etc., can solve the problems of large resin shrinkage rate and high curing temperature, and achieve good controllability, simple synthesis process, and excellent mechanical properties Effect

Active Publication Date: 2021-06-08
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, during the curing process of these materials, small molecules of water will be removed, and solvents with high boiling points need to be used, which has the problems of large resin shrinkage and high curing temperature.

Method used

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  • Degradable monomer based on cyclic acetal structure as well as synthesis method and application of degradable monomer
  • Degradable monomer based on cyclic acetal structure as well as synthesis method and application of degradable monomer
  • Degradable monomer based on cyclic acetal structure as well as synthesis method and application of degradable monomer

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[0033] Another aspect of the embodiments of the present invention provides a method for synthesizing a degradable monomer based on a cyclic acetal structure, which includes: making a substance containing hydroxybenzaldehyde, The mixed system of glycerol is reacted at 10-180°C to obtain a degradable monomer based on a cyclic acetal structure.

[0034] In some embodiments, the hydroxybenzaldehydes have a structure represented by the following formula:

[0035]

[0036] R 1 , R 2 , R 3 , R 4 , R 5 At least one of them is hydroxyl, at least the other is independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy or hydroxyl, and the rest are selected from H, substituted or unsubstituted alkyl, substituted or Unsubstituted alkoxy or hydroxy.

[0037] In some embodiments, the molar ratio of glycerol to hydroxybenzaldehydes is 1:1-10.

[0038] In some embodiments, the catalyst includes any one or a combination of p-toluenesulfonic aci...

Embodiment 1

[0069] (1) Take 15.2g of vanillin, 10g of glycerol and 0.15g of phosphoric acid and mix them without adding any solvent, and react at 110°C for 6h until the solid precipitation reaction ends. Wash with a small amount of water and acetone, filter with suction, and dry to obtain the final product. The structural formula is shown in the following formula I-1, and the yield is 90%. 1 H-NMR such as figure 1 As shown, there is a one-to-one correspondence between each peak on the figure and the hydrogen above the structure of formula I-1.

[0070]

[0071] (2) Take 10 g of the compound represented by formula I-1, 0.1 g of tetrabutylammonium bromide, and 25 g of 50 wt % potassium hydroxide aqueous solution, and react at 60° C. for 2 h. Then the temperature was lowered to below 10°C, and 50 g of epichlorohydrin was added dropwise through a constant pressure separating funnel, and the drop was completed within 0.5 h. After the dropwise addition was completed, the reaction was carr...

Embodiment 2

[0074] (1) Mix 15.2g of 2,4-dihydroxy-3-methylbenzaldehyde, 10g of glycerin and 0.15g of citric acid, add 30ml of N,N-dimethylformamide and 40ml of petroleum ether, and react at 100°C for 12h , until there is no more water in the water separator, the reaction is over. Then remove the upper layer of petroleum ether, wash with a small amount of water and acetone, filter with suction, and dry to obtain the final product. H NMR 1 H-NMR and infrared characterization confirmed that the structural formula of the final product was shown in the following formula I-2, and the yield was 80%.

[0075]

[0076] (2) Take 10 g of the compound represented by formula I-2, 10 g of tetrabutylammonium bromide, and 500 g of 50 wt % potassium hydroxide aqueous solution, and react at 10° C. for 2 h. Then the temperature was lowered to -5°C, and 500 g of epichlorohydrin was added dropwise through a constant pressure separating funnel, and the drop was completed within 5 hours. After the dropwis...

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Abstract

The invention discloses a degradable monomer based on an acetal structure and a synthesis method of the degradable monomer. The degradable monomer has a structure as shown in a formula I which is described in the specification. In the formula I, at least one of R<1>, R<2>, R<3>, R<4> and R<5> is a hydroxyl group, at least another one of R<1>, R<2>, R<3>, R<4> and R<5> is independently selected from substituted or unsubstituted alkyl group and a substituted or unsubstituted alkoxy or hydroxyl group, and the rest are selected from H, the substituted or unsubstituted alkyl group and the substituted or unsubstituted alkoxy or hydroxyl group. The invention also discloses a method for synthesizing epoxy resin by using the degradable monomer and the epoxy resin obtained by using the method. When the degradable monomer provided by the invention is used for synthesizing various materials such as the epoxy resin, the materials can be endowed with good degradability, excellent mechanical properties, excellent heat resistance and relatively high glass transition temperature; and the synthesis method is simple in process, easy and convenient to operate, good in controllability, easy to implement and suitable for large-scale industrial production; and wide application prospects are obtained in the fields of coatings, fiber composite materials, aerospace and the like.

Description

technical field [0001] The invention relates to a compound that can be used to prepare epoxy resin, in particular to a degradable monomer based on a cyclic acetal structure, its synthesis method and its application in epoxy resin, belonging to the technical field of polymer materials . Background technique [0002] Plastic plays a vital role in contemporary society. Due to its excellent performance, plastics have been widely used in furniture, daily necessities, medical care, agriculture, fishery, transportation, construction industry, chemical industry, aerospace and many other fields, driving the development of society and the progress of human civilization. However, the difficult problem of subsequent processing makes traditional plastics face severe challenges. The traditional incineration and landfill methods of waste plastics have serious defects, such as the greenhouse gas or toxic substances produced by the former and the waste and pollution of land resources by th...

Claims

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Application Information

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IPC IPC(8): C07D319/06C07D407/14C08G59/04
CPCC07D319/06C07D407/14C08G59/04Y02W30/62
Inventor 马松琪王滨搏朱锦
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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