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Norbornene group capping benzoxazine oligomer and preparation method thereof

An alkenyl-terminated, benzoxazine technology, applied in the direction of organic chemistry, to achieve the effect of simple preparation process, low equipment requirements, and improved processability

Active Publication Date: 2017-05-24
成都科宜高分子科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, so far there is no report on the synthesis and properties of benzoxazine oligomers containing norbornene-terminated groups.

Method used

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  • Norbornene group capping benzoxazine oligomer and preparation method thereof
  • Norbornene group capping benzoxazine oligomer and preparation method thereof
  • Norbornene group capping benzoxazine oligomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] A preparation method of a norbornene-terminated benzoxazine oligomer, the specific steps are:

[0039] (1) 10.9g (0.1mol) of 2-aminophenol and 16.4g (0.1mol) of norbornene dianhydride are added to the reaction flask, and 30ml of glacial acetic acid is added to the flask, and the reaction system is heated from room temperature to 120 ℃, stirred with a magnetic stirrer for 6 hours, poured the reacted mixture into deionized ice water for precipitation, collected the precipitate and dried it in a vacuum electric furnace for 10-12 hours to obtain 23.4 g of white product o-norbornene phenol, yield 92%. The reaction equation is as follows:

[0040]

[0041](2) Weigh 25.5g (0.1mol) of ortho-norbornene functionalized phenol obtained in the previous step, 30.0g (0.15mol) of 4,4-dihydroxydiphenylmethane, 4,4-diaminodiphenyl Methane (DDM) 39.6g (0.2mol), paraformaldehyde 24g (0.8mol) join in the reaction flask that stirrer, thermometer and condensing tube are housed, in reacti...

Embodiment 2

[0048] The 4,4-diaminodiphenylmethane in Example 1 was replaced with 4,4-diaminodiphenyl ether, and the other steps were the same as those in Example 1.

[0049] Wherein the specific chemical structure of 4,4-diaminodiphenyl ether is:

[0050] In the second step reaction, the amount of reactant was changed to: Weigh 25.5g (0.1mol) of ortho-norbornene functionalized phenol obtained in the previous step reaction, 30.0g (0.15mol) of 4,4-dihydroxydiphenylmethane mol), diaminodiphenyl ether 40.0g (0.2mol) and paraformaldehyde 24g (0.8mol).

[0051] The structural formula of gained benzoxazine oligomer is:

[0052]

[0053] After ring-opening and solidification of the benzoxazine oligomer obtained in this example, its glass transition temperature was measured to be 402° C., its 5% thermal weight loss temperature was 533° C., and its carbon residue rate at 800° C. was 75%.

Embodiment 3

[0055] Using bisphenol A and DDM as reactants

[0056] The 4,4-dihydroxydiphenylmethane in Example 1 was replaced with bisphenol A, and other steps were the same as those in Example 1.

[0057] Wherein the specific chemical structure of bisphenol A is:

[0058] In the second step reaction, the amount of reactants was changed to: Weigh 25.5g (0.1mol) of ortho-norbornene functionalized phenol obtained in the previous step reaction, 34.2g (0.15mol) of bisphenol A, 4,4- Diaminodiphenylmethane (DDM) 39.6 g (0.2 mol) and paraformaldehyde 24 g (0.8 mol).

[0059] The structural formula of gained benzoxazine oligomer is:

[0060]

[0061] After ring-opening and solidification of the benzoxazine oligomer obtained in this example, its glass transition temperature was measured to be 385° C., its 5% thermal weight loss temperature was 517° C., and its carbon residue rate at 800° C. was 71%.

[0062] The advantage of the present invention is to introduce cross-linkable and high tem...

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Abstract

The invention belongs to the technical field of heat convertible resins and preparation thereof, and discloses a norbornene group capping benzoxazine oligomer and a preparation method thereof. The preparation method comprises the concrete steps of carrying out condensation reaction on 2-aminophenol and carbic anhydride to prepare norbornene functionalized phenol containing a carbon-carbon double bond, and utilizing the norbornene functionalized phenol containing the carbon-carbon double bond as a capping group of the benzoxazine oligomer; utilizing the norbornene functionalized phenol containing the carbon-carbon double bond, bisphenol, diphenacylamine and paraformaldehyde to be subjected to Mannich condensation reaction in an organic solvent; preparing high-performance thermosetting resin through the benzoxazine oligomer. Compared with the prior art, the norbornene group capping benzoxazine oligomer and the preparation method thereof provided by the invention has the advantage that the cross-linkable capping group is introduced through ortho-position benzoxazine chemical so as to prepare the benzoxazine oligomer. The ortho-position benzoxazine chemical is utilized to enable a benzoxazine synthesis process to be simplified, the introduced cross-linkable capping group fills a performance gap of the benzoxazine oligomer caused by low molecular weight, and the machinability of abenzoxazine resin is improved.

Description

technical field [0001] The invention belongs to the technical field of thermosetting resin and its preparation, in particular to a method for preparing a benzoxazine oligomer by chemically introducing a crosslinkable norbornene group as an end-capping group through ortho-benzoxazine . Background technique [0002] Benzoxazines are a class of six-membered heterocyclic compounds synthesized by polycondensation reactions of phenolic compounds, amine compounds and formaldehyde. They were initially discovered in the Mannich reaction, and undergo ring-opening polymerization under the action of heating or catalysts to form nitrogen-containing and similar Network structure of phenolic resin. In 1944, Holly and Cope first discovered benzoxazine compounds when they synthesized Mannich reaction using o-hydroxyphenol, methylamine, and formaldehyde as raw materials; after 1949, Burke et al. conducted a systematic study on the synthesis of benzoxazines. , synthesized a series of compoun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14C08G73/06
CPCC07D413/14C08G73/06
Inventor 张侃仇嘉明韩璐申小娟陈星伟黎焜铨
Owner 成都科宜高分子科技有限公司
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