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Preparation method of diaza-naphthalenone-biphenyl-polybenzoxazole, monomer and polymer

A technology of phthalazinone biphenyl polybenzoxazole and xinaphthinone biphenyl polybenzoxazole, which is applied in the field of high-performance polymer materials, can solve the problems of time and energy consumption, complex synthesis process, trichloro Benzene toxicity and other issues

Inactive Publication Date: 2012-07-18
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In addition, the 4,6-diaminoresorcinol salt monomer (DAR.HCl) used in commercial PBO is generally prepared from trichlorobenzene through multi-step reactions. Trichlorobenzene is highly toxic and the synthesis process is complicated ,High cost
In addition, DAR is easily oxidized in the air and is often stored in the form of hydrochloride. It takes a lot of time for degassing during polymerization, which is time-consuming and energy-consuming.

Method used

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  • Preparation method of diaza-naphthalenone-biphenyl-polybenzoxazole, monomer and polymer
  • Preparation method of diaza-naphthalenone-biphenyl-polybenzoxazole, monomer and polymer
  • Preparation method of diaza-naphthalenone-biphenyl-polybenzoxazole, monomer and polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] In a reactor equipped with mechanical stirring, under the protection of nitrogen, add 3.5kg of 80% polyphosphoric acid, 2-(3-hydroxyl-4-aminophenyl)-4-[4-(3-amino-4- hydroxyphenoxy)]-2,3-naphthyridine-1-one (a, R 1 =R 2 =R 3 =R 4 =H) 0.500mol, terephthalic acid 0.500mol, add phosphorus pentoxide 0.12 kg, start stirring. The temperature was raised to carry out the polymerization reaction, and the reaction was carried out at 80°C for 2 hours, at 120°C for 8 hours, at 150°C for 10 hours, and at 185°C for 10 hours to obtain a viscous liquid. After the reaction is over, cool down to about 80°C, add deionized water to wash fully, filter, wash repeatedly with deionized water and dilute sodium bicarbonate solution until neutral, and vacuum dry at 100°C.

[0083] The chemical structure of the polymer was confirmed by infrared spectroscopy, the molecular weight was confirmed by high-performance gel chromatography (GPC) analysis, and the thermal stability was confirmed by ther...

Embodiment 2

[0085] The method is basically the same as in Example 1, wherein the raw material adopts four-functionality monomer b, c or d to replace 2-(3-hydroxyl-4-aminophenyl)-4-[4-(3-amino-4- hydroxyphenoxy)]-2,3-naphthyridine-1-one (a, R 1 =R 2 =R 3 =R 4 = H); other aromatic diacids or diacid chlorides other than terephthalic acid instead of terephthalic acid; 2-(3-hydroxy-4-aminophenyl)-4-(3-amino-4-hydroxyphenyl )-naphthyridine-1-one (a) and terephthalic acid in a molar ratio of 0.98-1.3:1 instead of 1:1; the solvent uses p-toluenesulfonic acid or concentrated sulfuric acid instead of polyphosphoric acid to make the solution mass concentration is 5-30%; the amount of phosphorus pentoxide shrinking agent is to make the solvent mass concentration 60-120%; the sedimentation agent is methanol, ethanol, alkali aqueous solution or a mixture of the above two, and the alkali aqueous solution is NaOH, KOH, Na 2 CO 3 , NaHCO 3 or K 2 CO 3 aqueous solution to replace deionized water; ...

Embodiment 3

[0088] In a reactor equipped with mechanical stirring, under the protection of nitrogen, add 1.5kg of 85% polyphosphoric acid, 2-methyl-4-(3-amino-4-hydroxyphenyl)-6-amino-7-hydroxy -2,3-naphthyridine-1-one (b, R 1 =R 2 =R 3 =R 4 =H) 0.250 mol, terephthalic acid 0.500 mol, 4,6-diaminoresorcinol hydrochloride 0.250 mol, 0.12 kg phosphorus pentoxide, start stirring, and heat up for polymerization. React at 100°C for 5 hours, 120°C for 10 hours, 150°C for 10 hours, and 185°C for 6 hours to obtain a viscous liquid. After the reaction is over, cool down to about 80°C, add deionized water to wash fully, filter, wash repeatedly with deionized water and dilute sodium bicarbonate solution until neutral, and vacuum dry at 100°C.

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Abstract

The invention belongs to the field of high performance macromolecule materials. Diaza-naphthalenone-biphenyl-polybenzoxazole utilizes a monomer with a diaza-naphthalenone-biphenyl structure. The diaza-naphthalenone-biphenyl-polybenzoxazole or a polymer of the diaza-naphthalenone-biphenyl-polybenzoxazole is obtained by adding the monomer and various diacid or acid halide of the diacid into polyphosphoric acid, adding or not adding other salt of diamido-diphenol and conducting high temperature solution polycondensation reaction on the mixture. The monomer with the diaza-naphthalenone-biphenyl structure is stable in performance, does not need to be salified, can save a degassing step in polymerization, and greatly shortens polymerization time. The polymer has excellent heat resistance, good mechanical performance, abrasion resistance, radiation resistance, optical-electrical characteristics and improves dissolubility and can be widely used in fields such as high heat resistant fiber, resin, composite materials, films and coatings of the fiber, biological materials, adhesives and high performance optical-electrical materials.

Description

technical field [0001] The invention belongs to the field of high-performance polymer materials, and relates to phthalazinone biphenyl polybenzoxazole, a copolymer and a preparation method thereof. Background technique [0002] Poly (p-phenylene-2,6-benzobisoxazole) PBO (Poly (p-phenylene-2,6-benzobisoxazole)) is a rigid rod-shaped ladder polymer composed of benzene rings and aromatic heterocycles, with high heat resistance, specific strength and specific modulus Higher than carbon fiber with excellent performance, it is the synthetic fiber with the highest strength and modulus. The decomposition temperature of PBO fiber in air is 650°C, and it can be used for a long time at 300°C. However, PBO has low compressive strength (200-400MPa) compared with high-performance carbon fibers. In addition, PBO is only dissolved in strong acid medium such as polyphosphoric acid and concentrated sulfuric acid, and the melting temperature is very high (higher than the decomposition temper...

Claims

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Application Information

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IPC IPC(8): C08G73/22C07D237/32
Inventor 朱秀玲罗亚军
Owner DALIAN UNIV OF TECH
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