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Bio-based bisphenol monomer containing fluorene ring structure, bio-based epoxy resin monomer, bio-based epoxy resin material and preparation methods thereof

An epoxy-based, bio-based technology, applied in the field of bio-based epoxy resin materials and their preparation, can solve the problems of non-specific immune function decline, hidden dangers of bisphenol A human health, and the reduction of the number of immune cells, so as to reduce the potential Effects of toxicity, dependence reduction, low estrogenic activity

Pending Publication Date: 2021-05-04
长春长光宇航复合材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the study of bisphenol A on the non-specific immune defense system of the host, it was found that the number of immune cells in the spleen of male mice injected with bisphenol A was significantly reduced, and the non-specific immune function was severely reduced.
A large number of animal experiments have proved that the intake of bisphenol A has a major hidden danger to human health

Method used

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  • Bio-based bisphenol monomer containing fluorene ring structure, bio-based epoxy resin monomer, bio-based epoxy resin material and preparation methods thereof
  • Bio-based bisphenol monomer containing fluorene ring structure, bio-based epoxy resin monomer, bio-based epoxy resin material and preparation methods thereof
  • Bio-based bisphenol monomer containing fluorene ring structure, bio-based epoxy resin monomer, bio-based epoxy resin material and preparation methods thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0056] The preparation method of bio-based epoxy resin monomer of the present invention comprises the following steps:

[0057] Step 1. Mix the bio-based bisphenol monomer containing the fluorene ring structure, epichlorohydrin (ECH) and tetrabutylammonium bromide uniformly, stir and react at 90°C for 6 hours to obtain the mixture;

[0058] Step 2. Distill the mixture obtained in Step 1 to remove excess epichlorohydrin, add toluene and sodium hydroxide aqueous solution, heat to 90°C and stir for 3 hours, cool down to room temperature, wash, remove toluene by vacuum distillation, and put After drying in an oven at 60°C for 12 hours, a golden yellow solid resin was obtained;

[0059] Step 3, after the golden yellow solid resin is recrystallized with ethanol, white needle-shaped resin crystals are obtained, that is, bio-based epoxy resin monomer;

[0060] The reaction equation is:

[0061]

[0062] In the above technical scheme, the ratio of bio-based bisphenol monomer conta...

Embodiment 1

[0074] In a four-neck flask equipped with a mechanical stirrer, a thermometer, a dropping funnel, and a reflux condensing device, add 0.04 mol of fluorenone, 0.08 mol of guaiacol, and 0.1 mL of 3-mercaptopropionic acid; Stir under low pressure until the fluorenone is fully dissolved in guaiacol; add 1.5mL concentrated sulfuric acid dropwise to the reaction system for 30 minutes; after the concentrated sulfuric acid is added dropwise, raise the temperature of the reaction system to 80°C and continue the reaction for 5h , when the reactant changed from liquid to solid, stop heating, after cooling, add deionized water to wash several times, obtain a golden yellow crude product after suction filtration, recrystallize the golden yellow crude product with toluene and cool to room temperature to obtain White needle-like crystals, which are bio-based bisphenol monomers containing fluorene ring structure (9,9'-bis(3-methoxy-4-hydroxyphenyl)fluorene).

Embodiment 2

[0076] Add 41.04 g of 9,9'-bis(3-methoxy-4-hydroxyphenyl)fluorene prepared in Example 1, 160 mL of epichlorohydrin and four 1g of butyl ammonium bromide, mixed evenly, heated to 90°C and reacted for 6 hours. After the reaction, the excess epichlorohydrin in the system was removed by vacuum distillation. After the epichlorohydrin was completely removed, the reaction system Add 160mL of toluene and 28.8g of aqueous sodium hydroxide solution (wt=50%) to the mixture, and continue to react at 90°C for 3h. Dry at 60°C for 12 hours to obtain a golden yellow solid resin. After recrystallization of the golden yellow solid resin with ethanol, a white needle-like resin crystal is obtained, that is, a bio-based epoxy resin monomer (9,9'-bis(3-methanol) Oxy-4-glycidyl ether phenyl) fluorene).

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Abstract

The invention relates to a bio-based bisphenol monomer containing a fluorene ring structure, a bio-based epoxy resin monomer, a bio-based epoxy resin material and preparation methods thereof, and belongs to the technical field of high molecular material. The technical problems that an epoxy resin material in the prior art depends on petrochemical engineering resources and has potential toxicity are solved. The structural formula of the bio-based bisphenol monomer containing the fluorene ring structure is shown in the specification. The bio-based bisphenol monomer containing the fluorene ring structure takes a natural product guaiacol as a raw material and has relatively low estrogen activity. The bio-based epoxy resin monomer prepared from the raw material of the low-estrogen- activity bio-based bisphenol monomer containing the fluorene ring structure through a one-step method can effectively reduce the dependence of the epoxy resin material on petrochemical engineering, and reduce the potential toxicity of the epoxy resin material, so that the prepared bio-based epoxy resin material can meet the performance requirements of the existing epoxy resin material.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a bio-based bisphenol monomer containing a fluorene ring structure, a bio-based epoxy resin monomer, a bio-based epoxy resin material and a preparation method thereof. Background technique [0002] Epoxy resins are widely used in electronic packaging materials, coatings, electronic devices, adhesives, and composite materials because of their excellent comprehensive properties. In a variety of thermosetting resin materials, it occupies a large proportion of applications. But at present, there are two main factors restricting the development of epoxy resin materials. [0003] First, the raw materials for the preparation of epoxy resin are bisphenol monomer and epichlorohydrin. Almost all of them come from petrochemical industry, and as a non-renewable resource, the storage of fossil fuel is extremely limited. According to reports, based on the global annual...

Claims

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Application Information

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IPC IPC(8): C07C43/23C07C41/30C07D303/28C07D301/28C08G59/24C08G59/42C08L63/00
CPCC07C43/23C07C41/30C07D303/28C07D301/28C08G59/245C08G59/4215C08L63/00C07C2603/18
Inventor 姜昊林再文商伟辉邹志伟卜凡哲
Owner 长春长光宇航复合材料有限公司
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