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Benzoxazole resin and method for preparing same

A technology of benzoxazole and benzoxazine, which is applied in the field of thermosetting resin and its preparation, can solve the problems of easy ring-opening decomposition of benzoxazole ring and incomplete removal of phosphoric acid solvent, etc. Effects in simple steps

Active Publication Date: 2017-07-28
成都科宜高分子科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In these patents, although benzoxazole and its derivatives were successfully prepared, further analysis of such synthesis schemes found that the phosphoric acid solvent could not be completely removed during the reaction process, resulting in the benzoxazole and benzoxazole derivatives in the long-term use of the product under high humidity and high temperature conditions. Defects of easy ring-opening and decomposition of oxazole ring
In addition, so far there is no report on the synthesis and properties of fluorine-containing benzoxazole resins based on fluorine-containing amidobenzoxazines.

Method used

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  • Benzoxazole resin and method for preparing same
  • Benzoxazole resin and method for preparing same
  • Benzoxazole resin and method for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The specific steps are:

[0043] (1) First add 21.82g of 2-aminophenol to 100mL of tetrahydrofuran solvent system, fully mix and dissolve in an ice bath, add 21.00g of trifluoroacetic anhydride dropwise after 15 minutes, and continue to react in an ice bath after adding 1.5 hours. After the reaction was finished, the solvent was removed by suspension evaporation, and the product was dissolved in ethyl acetate, washed three times with 5% sodium bicarbonate solution and deionized aqueous solution, and then the solvent was removed to obtain 17.64 g of the product o-trifluoroacetamide phenol. 82%. The reaction equation is as follows:

[0044]

[0045] (2) Weigh 10.26 g of o-trifluoroacetamide phenol, 4.96 g of diphenylmethanediamine, and 3.20 g of paraformaldehyde prepared in step (1) and mix them in 100 mL of xylene solvent, then heat up to 120° C., and the reaction time is 6 h. After stopping the reaction, wash with lye and evaporate the solvent to obtain a solid, a...

Embodiment 2

[0053] The reactant diphenylmethanediamine in the second step in Example 1 is replaced by 4,4'-diaminodiphenyl ether, the amount of reactant is changed accordingly, and other operating steps are the same as those in Example 1 .

[0054]In the second step reaction, the amount of the reactant was changed to: 10.26 g of o-trifluoroacetamide phenol obtained from the previous step reaction, 3.20 g of paraformaldehyde, and 5.01 g of 4,4'-diaminodiphenyl ether, to obtain Product 13.66g, yield 83%.

[0055] The specific chemical structure of the main chain type polybenzoxazine obtained is:

[0056]

[0057] Wherein the specific chemical structure of polybenzoxazole obtained is:

[0058]

[0059] The temperature of the benzoxazole resin obtained in this embodiment is 486° C. when the thermal weight loss is 5%, and the carbon residue rate at 800° C. is 69%. The dielectric constant of the benzoxazole resin is 2.3 at room temperature and 1 MHz.

Embodiment 3

[0061] The reactant diphenylmethanediamine in the second step in the embodiment 1 is replaced by 4,4'-diaminobenzophenone, and the amount of the reactant is changed accordingly, and other operation steps are the same as those in the embodiment 1 step.

[0062] In the second step reaction, the amount of the reactant was changed to: 10.26g of o-trifluoroacetamide phenol obtained from the previous step reaction, 3.20g of paraformaldehyde, 5.31g of 4,4'-diaminobenzophenone, 13.59 g of the product was obtained with a yield of 81%.

[0063] The specific chemical structure of the main chain type polybenzoxazine obtained is:

[0064]

[0065] Wherein the specific chemical structure of polybenzoxazole obtained is:

[0066]

[0067] The polybenzoxazole obtained in this example has a temperature of 501° C. when the thermal weight loss is 5%, and a carbon residue rate of 72% at 800° C., and the dielectric constant of the benzoxazole resin is 2.5 at room temperature and 1 MHz.

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Abstract

The invention provides high-performance fluorine-containing benzoxazole resin and a method for preparing the same. The high-performance fluorine-containing benzoxazole resin is prepared from flutolanil-containing benzoxazine intermediates. An integral procedure for preparing the high-performance fluorine-containing benzoxazole resin includes three steps of firstly, carrying out reaction on 2-amine phenol and trifluoroacetic anhydride to obtain ortho-trifluoroacetamide phenol; secondly, carrying out reaction on the ortho-trifluoroacetamide phenol, diamine compounds and formaldehyde to synthesize ortho-position flutolanil-containing benzoxazine monomers; thirdly, preparing solution with certain concentration from the ortho-position flutolanil-containing benzoxazine monomers prepared at the previous step, carrying out thermosetting on benzoxazine and carrying out thermal cyclization on benzoxazole so as to obtain high-performance benzoxazole thermoset resin materials. The high-performance fluorine-containing benzoxazole resin and the method have the advantages that the method for preparing the benzoxazole resin includes the simple steps and is environmentally friendly, and raw materials for the benzoxazole resin are easily available; the benzoxazole resin prepared by the aid of the method is high in thermal stability and low in dielectric constant and production cost, and accordingly the benzoxazole resin and the method are suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of thermosetting resin and its preparation, and in particular relates to an ortho-fluorine-containing benzoxazine (intermediate), a high-performance fluorine-containing benzoxazole resin and a preparation method thereof. [0002] technical background [0003] With the development of aerospace technology, especially the improvement of the flight speed of spacecraft and the ratio of payload to structure mass, high-temperature-resistant advanced composite materials are becoming the most important new aerospace structural materials, especially high-temperature-resistant composite materials. Must have very good high temperature properties. Benzoxazole resin has excellent mechanical properties and electrical properties, and is one of the ideal matrix resins for high temperature resistant composite materials. [0004] Among the relevant patents reported so far, there are several methods for synthesizing polybenzoxa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/22C08L79/04
CPCC08G73/22C08L79/04
Inventor 张侃喻馨叶孙林
Owner 成都科宜高分子科技有限公司
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