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Benzoxazine monomer containing ethynyl groups and norbornene and preparation method and application of benzoxazine monomer

A technology of norbornene and benzoxazine, which is applied in the field of benzoxazine monomer and its preparation, can solve the problems of excessively high processing temperature, increase of preparation cost, high thermal curing temperature of norbornene, and reduce the processing temperature , improve thermodynamic properties, simple preparation process

Active Publication Date: 2019-02-01
镇江利德尔复合材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Then, according to previous research reports, the thermal curing temperature of norbornene is as high as about 350°C (Macromolecules 1997, 30, 515-519; Macromolecules, 2017, 50, 6081-6087), which brings certain difficulties to the processing of polymers. difficulty
In addition, too high processing temperature also significantly increases the preparation cost, thus limiting the wide application of norbornene series polymers

Method used

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  • Benzoxazine monomer containing ethynyl groups and norbornene and preparation method and application of benzoxazine monomer
  • Benzoxazine monomer containing ethynyl groups and norbornene and preparation method and application of benzoxazine monomer
  • Benzoxazine monomer containing ethynyl groups and norbornene and preparation method and application of benzoxazine monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The specific steps are:

[0037] (1) Norbornene dioic anhydride 1g, o-aminophenol 0.665g, 40mL glacial acetic acid (AcOH) are respectively added in the reaction vessel equipped with stirring magnet and condenser, the reaction unit is moved to the oil bath, 120 ℃ of reaction for 6 hours, after the reaction, the reaction solution was poured into 150 mL of deionized water to obtain a large amount of precipitation, after suction filtration, washed three times with a large amount of deionized water, and put into a 60 ℃ vacuum drying box to obtain the product ortho-norbornene Functionalized phenol 1.435 g, yield 92%. The reaction equation is as follows:

[0038]

[0039] (2) Weigh 1 g of ortho-norbornene functionalized phenol and 0.459 g of 4-ethynylaniline, 0.254 g of paraformaldehyde, and 40 mL of xylene prepared in step (1), respectively, and add them to a stirring magnet and a condenser. In the reaction vessel of the tube, the reaction was carried out at 120 ° C for ...

Embodiment 2

[0047] The reactant 4-ethynylaniline in the second step in Example 1 was replaced with 3-ethynylaniline, and other operation steps were the same as those in Example 1 to obtain 1.256 g of the product with a yield of 82%.

[0048] The specific chemical structure of the obtained main chain polybenzoxazine is:

[0049]

[0050] The temperature of the benzoxazole resin obtained in this example is 428° C. when the thermal weight loss is 5%, the carbon residue rate at 800° C. is 63%, and the dielectric constant of the benzoxazole resin at room temperature and 1 MHz is 2.7.

Embodiment 3

[0052] The reactant 4-ethynylaniline in the second step in Example 1 was replaced with 2-ethynylaniline, and other operation steps were the same as those in Example 1 to obtain 1.364 g of the product with a yield of 88%.

[0053] The specific chemical structure of the obtained main chain polybenzoxazine is:

[0054]

[0055] The benzoxazole resin obtained in this example has a temperature of 443° C. at a thermal weight loss of 5%, a carbon residue rate of 68% at 800° C., and a dielectric constant of 2.6 at room temperature and 1 MHz of the benzoxazole resin.

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PUM

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Abstract

The invention belongs to the technical field of thermosetting resin, and discloses benzoxazine monomer containing ethynyl groups and norbornene and a preparation method and application of the benzoxazine monomer. According to the preparation method, ortho-norbornene-functionalized phenol is firstly synthesized by using norbornene dianhydride and o-aminophenol, and then the benzoxazine monomer containing ethynyl groups and norbornene is prepared by using the ortho-norbornene-functionalized phenol, ethynyl-containing aniline and paraformaldehyde in a low-polarity solvent. In addition to curablecross-linking of oxazine rings, curing cross-linking can also be performed on carbon-carbon double bonds and ethynyl groups in norbornene groups; the curing temperature of the norbornene groups is reduced significantly through introduction of the ethynyl groups, and is reduced from 350 DEG C to 220 DEG C, so that the processability of the resin is improved; not only can a new variety be added to benzoxazine compounds, but also the thermodynamic properties of the resin material can be improved significantly by a multiple-crosslinked network system formed through curing of the resin; and the preparation method has the advantages of simpleness, high operability, high yield, low production cost and easy industrial production.

Description

technical field [0001] The invention relates to a benzoxazine thermosetting resin and a preparation method thereof, in particular to a benzoxazine monomer containing an ethynyl group and norbornene and a preparation method thereof. Background technique [0002] Benzoxazine monomer is a heterocyclic structure composed of oxygen and nitrogen atoms, and the chemical structural formula is as follows: [0003] [0004] As a raw material for the preparation of a new type of thermosetting resin, benzoxazine monomer can undergo ring-opening polymerization under certain conditions to generate cross-linking to form a structure similar to phenolic resin. The characteristics of this resin are that it has good heat resistance, flame retardancy, low curing shrinkage and no release of small molecules, high glass transition temperature, and so on. Moreover, the molecular structure of benzoxazine is flexible and changeable, and has high controllability. By introducing monomers of phenol ...

Claims

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Application Information

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IPC IPC(8): C07D413/04C08G14/073
CPCC07D413/04C08G14/06
Inventor 张侃喻馨叶刘宇奇王雨亭韩梦超
Owner 镇江利德尔复合材料有限公司
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