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Bio-based benzoxazine precursor based on soya bean derivative, and preparation method and application of same

A technology of soybean derivatives and precursors, applied in the direction of organic chemistry, can solve the problems of low relative molecular weight, low elongation at break, and limited application range of polymers, and achieve simple and efficient preparation methods, high cross-linking density, The effect of saving oil resources

Active Publication Date: 2018-08-24
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, bio-based benzoxazine resins also have many disadvantages like traditional benzoxazine resins: monofunctional benzoxazines have chain transfer reactions during ring-opening polymerization, and the relative molecular weight of the resulting polymers Due to the characteristics of the molecular structure of bifunctional benzoxazines, their polymers also have disadvantages such as low crosslinking density, low elongation at break, and poor toughness.

Method used

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  • Bio-based benzoxazine precursor based on soya bean derivative, and preparation method and application of same
  • Bio-based benzoxazine precursor based on soya bean derivative, and preparation method and application of same
  • Bio-based benzoxazine precursor based on soya bean derivative, and preparation method and application of same

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Dissolve 1 mol of soybean isoflavone, 2 mol of furfurylamine, and 6 mol of paraformaldehyde in 500 mL of a mixed solution of dioxane and toluene (weight ratio 3:1), react at 90°C for 32 hours, and remove by rotary evaporation under reduced pressure. Mixed solvents, washed with water and dried to obtain soybean isoflavone furfurylamine benzoxazine precursor, the yield is 91.5%, H NMR spectrum 1 H-NMR such as figure 1 As shown, each peak on the figure is in one-to-one correspondence with the hydrogen atoms on the structure of soybean isoflavone furfurylamine benzoxazine compound.

[0034] The soybean isoflavone furfurylamine benzoxazine precursor is heated in a blast oven, and finally cured at 260° C. to obtain the soybean isoflavone furfurylamine polybenzoxazine resin. The glass transition of the resulting cured product is 410 °C, T d10 The temperature is 467°C, the storage modulus is 3500MPa, and the salt spray resistance test time is 400h.

Embodiment 2

[0036] Dissolve 1 mol of soybean isoflavone, 2 mol of aniline, and 7.5 mol of paraformaldehyde in a mixed solution of 650 mL of dioxane and toluene (weight ratio 2:1), react at 100°C for 52 hours, and remove by rotary evaporation under reduced pressure. After mixing solvents, washing with water and drying, soybean isoflavone aniline benzoxazine precursor is obtained, and the yield is 90.8%. H NMR spectrum 1 H-NMR such as figure 2 As shown, each peak on the figure is in one-to-one correspondence with the hydrogen atoms on the structure of soybean isoflavone aniline benzoxazine compound.

[0037]The soy isoflavone aniline benzoxazine precursor is heated in a forced air oven and finally cured at 260° C. to obtain a soy isoflavone aniline polybenzoxazine resin. The glass transition of the resulting cured product is 390 °C, T d10 The temperature is 471°C, the storage modulus is 3700MPa, and the salt spray resistance test time is 290h.

Embodiment 3

[0039] Dissolve 1mol soybean isoflavone, 2mol ethylamine, and 6.1mol paraformaldehyde in a mixed solution of 550mL dioxane and toluene (weight ratio 3:2), react at 120°C for 24 hours, and rotate under reduced pressure The mixed solvent was removed by evaporation, washed with water and dried to obtain a precursor of soybean isoflavone benzoxazine with a yield of 95.5%.

[0040] The soybean isoflavone ethylamine benzoxazine precursor is heated to 260° C. and finally solidified in a blast oven to obtain the soybean isoflavone ethylamine polybenzoxazine resin. The glass transition of the resulting cured product is 370 °C, T d10 The temperature is 441°C, the storage modulus is 3450MPa, and the salt spray resistance test time is 250h.

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Abstract

The invention provides a bio-based benzoxazine precursor based on a soya bean derivative, which has the structure as the formula (I). A preparation method includes the following steps: blending soy isoflavone, monoamine and paraformaldehyde and carrying out a cyclization reaction under heating for preparing the bio-based benzoxazine precursor. The preparation method is simple in preparation and operation, has good controllability, is easy to carry out and is suitable for large scale industrial production. Thermosetting polybenzoxazine resin prepared through ring-opening polymerization of the bio-based benzoxazine precursor has excellent anti-corrosion, mechanical and thermal performances and has possibility of replacing a petroleum-base product in the prior art, and has wide application range.

Description

technical field [0001] The invention belongs to bio-based thermosetting resins, in particular to a bio-based benzoxazine precursor based on soybean derivatives and its preparation method and application. Background technique [0002] Benzoxazine resin is a new type of phenolic resin. Because of its excellent comprehensive properties, it is widely used in anti-corrosion coatings, adhesives, microelectronics, aerospace and other fields. It is a very important class of thermosetting materials. However, most of the benzoxazine resins at this stage are derived from petroleum resources, and petroleum resources are an unsustainable resource. With the decrease of its reserves, the cost of polymer materials derived from petroleum resources will inevitably increase. raised. Recently, under the dual pressure of protecting the environment and saving petroleum resources, bio-based polymer materials using sustainable resources as raw materials have entered people's field of vision, and r...

Claims

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Application Information

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IPC IPC(8): C07D498/04C08G73/02
CPCC07D498/04C08G73/02
Inventor 代金月刘小青腾娜彭云燕朱锦
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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