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AB type poly(p-phenyl) benzdioxan monomer and its preparation and use

A technology of benzobisoxazole and benzoxazole, which is applied to the application field in the preparation of PBO resin, can solve the problems of high price, difficulty in solving DAR, and high operation cost of PBO preparation, and achieves easy operation, cost reduction and operation. handy effect

Inactive Publication Date: 2005-07-27
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to solve this problem, although there is a process of forming TPA salt and then polycondensation using the patents of Toyobo Corporation (US20010014756, US5919890, EP1108709), DAR is still used as raw material, which does not solve the difficulty of DAR preparation in essence, and is extremely easy to oxidize and decompose. The current situation of high price and extremely high PBO preparation operation cost has begun to hinder the application of high-performance PBO materials

Method used

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  • AB type poly(p-phenyl) benzdioxan monomer and its preparation and use
  • AB type poly(p-phenyl) benzdioxan monomer and its preparation and use
  • AB type poly(p-phenyl) benzdioxan monomer and its preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Preparation of 5-nitro-6-hydroxyl-2-(p-methoxycarbonylphenyl)benzoxazole (NHAB)

[0037] Take 15.18g 4-amino-6 nitroresorcinol hydrochloride (ANR HCl, 0.073mol) plus 13.57g p-methoxycarbonylbenzoyl chloride (MBC, 0.068mol) and add 120ml of solvent diethylene glycol dimethyl In ether, heat up to dissolve, react at 122-128°C for 2 hours, add 47.5g of polyphosphoric acid and then heat up to 156-160°C for about 3 hours, then add water for water analysis, filter, wash the filter cake with water, and dry to obtain the crude product of NHAB 20.85 g, HPLC purity 89.61%, crude product yield 90.33%; 14-dioxane with 10 times the crude product quality was selected for reflux decolorization and recrystallization to obtain 14.05g of NHAB fine product with a purity of 98.62%, a refined yield of 54.96%, and a melting point of : 234.8-235.5°C. IR (KBr, cm -1 ): 3320~3110(b, m), 3106.8(m), 1724.0(s), 1545.7(s), 1440.6(s), 1332.6(s), 1283.4(s), 708.7(s). 1 H NMR (500MHz CDCl...

Embodiment 2～8

[0042] Embodiment 2~8: the preparation of NHAB

[0043] For the synthesis of NHAB, according to the difference between the prepared ANR and ANR·HCl, the two monomers were used to test respectively. Adopt the same operation of embodiment 1, get different parameters to test by the parameter scope of the present invention, the results are shown in Table 1:

[0044] implement

[0045] The results show that: the NHAB synthesized by ANR as the raw material has a refined product yield of 47.10% and a refined purity of 95.22%; while the NHAB synthesized by ANR·HCl as a raw material has a purity of 85.44%, a yield of 87.32%, and a refined purity of 96.98%. Yield 52.71%; Visible synthetic NHAB is still better to adopt ANR HCl as raw material, it has higher yield than ANR raw material likewise, but the yield of NHAB especially when excessive MBC proportioning and lower PPA consumption Decrease faster; and the purity of NHAB obtained is not high, generally all about 90%, so the...

Embodiment 9～13

[0046] Embodiment 9~13: the refinement of NHAB

[0047] Adopt the same operation of embodiment 1 to refine and purify the NHAB crude product, get the following two methods of different parameters (two kinds of solvents and proportioning) by the parameter scope of the present invention to carry out purification effect test, simultaneously to adopting the DMF outside the present invention The refining invalidity result of solvent is carried out comparative test, and the results are shown in Table 2:

[0048] implement

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Abstract

A 5- amino-6-hydroxy-2-MAB and its production are disclosed. The production is carried out by: (1) R1-R2, green synthesizing 4-amino-6-ANR.HCL by resorcinol; (2) R3: preparing AB monomer precursor 5-nitro-6-hydroxy-2-NHAB, and refining purifying; (3) R4: catalyst hydrogenating reducing NHBA nitro group, and obtaining high-purity AB PBO monomer. It achieves simple process, short polymeric time and normal polymeric apparatus.

Description

(1) Technical field [0001] The invention relates to a new AB-type poly-p-phenylenebenzobisoxazole (PBO) monomer: 5-amino-6-hydroxyl-2-(p-methoxycarbonylphenyl)benzoxazole, and a preparation method thereof And its application in the preparation of PBO resin. (2) Background technology [0002] PBO is the abbreviation of cis-poly(p-phenylene-2,6-benzobisoxazole), which is the most organic and inorganic fiber by polymer liquid crystal spinning technology. High-performance fiber - Zylon, in addition to excellent spinning technology, the degree of polymerization and molecular weight of PBO is the key to directly affect the mechanical properties of the fiber. [0003] Research so far, Japan Toyobo (Toyobo) company patent (patent open 2000-38371) under high shear conditions through (1) formula by 4,6-diaminoresorcinol hydrochloride (DAR) and hydroquinone Formic acid (TPA) polycondensation reaction obtains the intrinsic viscosity of PBO resin up to 38dl / g, and the obtained ZylonHM ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/54C08G73/22
Inventor 金宁人胡建民王学杰张燕峰
Owner ZHEJIANG UNIV OF TECH
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