Dibenzoxazine containing oxazole ring and preparation method thereof

A technology of benzoxazine and fenoxazole rings, which is applied in the field of bisbenzoxazine and its preparation, can solve the problems of high curing temperature, inconvenient processing, and unsatisfactory conditions, and achieve low equipment requirements, simple preparation process, thermal good stability effect

Inactive Publication Date: 2011-11-23
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The double-terminated phthalonitrile-benzoxazine resin mentioned in Chinese patent ZL200610021851.X has a 5% weight loss temperature of 498°C, but its curing temperature is as high as 280°C, which brings inconvenience to the processing.
[0007] These patents improve the heat resistance of the polymer by improving the monomer structure of benzoxazine, but it is not ideal enough
Moreover, the dielectric constant of the polymer is not mentioned in this kind of invention patent. It is well known that a lower dielectric constant is very important for the application of polymers in dielectric functional materials.
In addition, so far there is no report related to the synthesis and properties of bisbenzoxazine with fenoxazole ring structure

Method used

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  • Dibenzoxazine containing oxazole ring and preparation method thereof
  • Dibenzoxazine containing oxazole ring and preparation method thereof
  • Dibenzoxazine containing oxazole ring and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] A kind of preparation method of the dibenzoxazine containing oxazole ring, concrete steps are,

[0042] (1) 5.00g of 4,6-diaminoresorcinol dihydrochloride (abbreviated as DAR), 75gPPA and 6.48g p-hydroxybenzoic acid are added to the reaction flask equipped with stirrer, thermometer and condenser tube , and heated to 60°C for stirring. Subsequently, the reaction device was evacuated with a vacuum pump, and then filled with nitrogen, and this was repeated three times. Then, under the condition of feeding nitrogen for protection, the temperature of the system was raised to 90°C at a rate of 10°C / hour, the nitrogen flow was stopped, and the foam in the reaction bottle was removed by vacuuming, and repeated several times until the foam was stable, and then respectively React at 90°C for 6 hours, 100°C for 6 hours, 130°C for 8 hours, 150°C for 8 hours, and 180°C for 8 hours. Cool to below 80°C, add 300mL of distilled water into it, stir, boil for 10 minutes, then cool natur...

Embodiment 2

[0051] The DAR in Example 1 is replaced by 6CDAR, the amount of reactants is changed accordingly, and other operating steps are the same as those in Example 1.

[0052] The specific chemical structure of 6CDAR is:

[0053]

[0054] In the first step reaction, the amount of reactant is changed to: 6CDAR is 5.00g, PPA is 75gPPA, p-hydroxybenzoic acid 4.16g.

[0055] In the second step reaction, the amount of the reactant was changed to: 1.00 g of diphenol obtained from the previous step reaction, 0.26 g of paraformaldehyde, and 0.40 g of aniline.

[0056] The structural formula of gained oxazine monomer is:

[0057]

[0058] After ring-opening polymerization of the oxazine monomer obtained in this example, the dielectric constant of the polymer is 2.0, the 5% weight loss temperature of the polymer is 483° C., and the residual carbon rate at 800° C. is 57%.

Embodiment 3

[0060] In Example 1, DAR in Example 1 is replaced by 6FDAR, aniline is replaced by m-aminophenylacetylene, and the amount of reactants is changed accordingly. Other operating steps are the same as those in Example 1.

[0061] The specific chemical structure of 6FDAR is:

[0062]

[0063] In the first step reaction, the amount of reactant is changed to: 6FDAR is 5.00g, PPA is 75gPPA, p-hydroxybenzoic acid 3.14g.

[0064] In the second step reaction, the amount of the reactant was changed to: 1.00 g of diphenol obtained from the previous step reaction, 0.21 g of paraformaldehyde, and 0.41 g of m-aminophenylacetylene.

[0065] The structural formula of the obtained oxazine monomer is:

[0066]

[0067] After ring-opening polymerization of the oxazine monomer obtained in this example, the dielectric constant of the polymer is 1.7, the 5% weight loss temperature of the polymer is 550° C., and the residual carbon rate at 800° C. is 61%.

[0068] The advantage of the present ...

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Abstract

The invention relates to a dibenzoxazine containing an oxazole ring and a preparation method thereof. The preparation method comprises the following two steps of: 1: mixing ortho-aminophenol hydrochloride and para-hydroxybenzoic acid, adding polyphosphoric acid as a solvent, reacting at 60-180 DEG C for 24-60 hours, and washing by using deionized water, filtering and drying to obtain diphenol containing an oxazole ring structure; and 2: mixing the diphenol containing the oxazole ring structure, phenylamine and paraformaldehyde, reacting at 80-110 DEG C for 40-80 minutes, then filtering and precipitating, washing 4-8 times by using alkali liquor, and then washing, filtering and drying to obtain the product. The dibenzoxazine disclosed by the invention has the advantages of very good mechanical property because the high temperature resistant oxazole ring structure is introduced to a benzoxazine molecule structure, dielectric constant of only 1.6-2.3, simple process, lower equipment requirement and suitability for large-scale production.

Description

【Technical field】 [0001] The invention relates to the technical field of thermosetting resins, in particular to a bisbenzoxazine containing an oxazole ring and a preparation method thereof. 【Background technique】 [0002] Phenolic resin is widely used due to its good heat resistance, flame retardancy, mechanical strength, corrosion resistance and electrical insulation, but due to the need for high temperature or strong acid catalyzed curing, small molecule volatiles are emitted during curing, etc. Disadvantages, often its use is limited. Benzoxazine is a six-membered heterocyclic ring system composed of oxygen atoms and nitrogen atoms. It can be ring-opened and polymerized under heating and / or catalysis to form a polybenzoxazine resin with a structure similar to polyphenolic formaldehyde. In addition to the advantages of heat resistance, flame retardancy, mechanical strength, corrosion resistance and electrical insulation equivalent to ordinary phenolic resins, benzoxazine ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/04C07D413/14C09K19/34C08G73/06
Inventor 刘小云张侃杜秀明杨光庄启昕韩哲文
Owner EAST CHINA UNIV OF SCI & TECH
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