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Polyaryletherketone resin with carbazole ring in main chain and preparation method thereof

A polyaryletherketone and carbazole ring technology is applied in the field of polyaryletherketone resin and its preparation, which can solve problems such as limiting the scope of application, and achieve the effects of simple process, low cost and good mechanical properties

Inactive Publication Date: 2013-02-13
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In this patent, although the large Cardo side group in the phenolphthalein bisphenol monomer endows the polymer molecular chain with a certain rigidity and good dissolution processability, the glass transition temperature of the polymer is 228°C, but with the development of science and technology, people There is an urgent need for polymers with higher heat resistance, and the glass transition temperature of this polyaryletherketone limits its application range to some extent

Method used

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  • Polyaryletherketone resin with carbazole ring in main chain and preparation method thereof
  • Polyaryletherketone resin with carbazole ring in main chain and preparation method thereof
  • Polyaryletherketone resin with carbazole ring in main chain and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] combine Figure 1-3 Illustrative Example 1

[0083] The preparation method of the polyaryletherketone resin containing N-ethylcarbazole ring structure in the main chain:

[0084] (1) Preparation of 3.6-bis(4-fluorobenzoyl)-N-ethylcarbazole monomer

[0085] N-ethylcarbazole 19.52g (0.10mol) and CHCl 3 Solvent 150mL is added in the flask that magneton is housed, under ice-water bath condition, add anhydrous aluminum trichloride 33.35g (0.25mol) in batches, add p-fluorobenzoyl chloride 26.00mL ( 0.22mol), after the dropwise addition, remove the ice-water bathroom temperature reaction (24 ℃) for 12h, then quench it with aqueous hydrochloric acid, extract the organic phase with ethyl acetate, dry it with anhydrous sodium sulfate, concentrate it by rotary evaporation and wash it with ethyl acetate Recrystallization to obtain 3.6-bis(4-fluorobenzoyl)-N-ethylcarbazole monomer;

[0086] (2) In a nitrogen atmosphere, 3.1833 grams (0.01mol) of phenolphthalein, 4.3945 grams (0....

Embodiment 2

[0094]The preparation method of the polyaryletherketone resin containing N-methylcarbazole ring structure in the main chain:

[0095] (1) Preparation of 3.6-bis(4-fluorobenzoyl)-N-methylcarbazole monomer

[0096] Add 10 g (0.061 mol) of carbazole and 80 mL of nitrobenzene solvent into a flask equipped with a magnet, add 17.54 g (0.13 mol) of anhydrous aluminum trichloride in batches under ice-water bath conditions, and then add to the reaction Add 15.36mL (0.13mol) of p-fluorobenzoyl chloride dropwise into the bottle. After the dropwise addition, remove the ice-water bathroom temperature reaction (24°C) for 15h, and then quench it with aqueous hydrochloric acid. The crude solid product obtained after filtration is heated Dissolve completely in the tetrahydrofuran solvent under reflux conditions, then add silica gel powder to the above tetrahydrofuran solution and reflux for 4 hours, then filter the silica gel powder while hot, and obtain 3,6-bis(p-fluorobenzoyl)- N(H)carbazol...

Embodiment 3

[0102] The preparation method of the polyaryletherketone resin containing N-hexylcarbazole ring structure in the main chain:

[0103] (1) Preparation of 3.6-bis(4-fluorobenzoyl)-N-hexylcarbazole monomer

[0104] N-hexylcarbazole 25.12g (0.10mol) and CHCl 3 Solvent 150mL is added in the flask that magneton is housed, under ice-water bath condition, add anhydrous aluminum trichloride 33.35g (0.25mol) in batches, add p-fluorobenzoyl chloride 26.00mL ( 0.22mol), after the dropwise addition, remove the ice-water bathroom temperature reaction (24 ℃) for 12h, then quench it with aqueous hydrochloric acid, extract the organic phase with ethyl acetate, dry it with anhydrous sodium sulfate, concentrate it by rotary evaporation and wash it with ethyl acetate Recrystallization to obtain 3.6-bis(4-fluorobenzoyl)-N-hexylcarbazole monomer;

[0105] (2) In a nitrogen atmosphere, 100.0000 grams (0.31mol) of phenolphthalein, 153.7476 grams (0.031mol) of 3.6-bis(4-fluorobenzoyl)-N-hexylcarbazo...

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Abstract

The invention discloses a polyaryletherketone resin with a carbazole ring in a main chain and a preparation method thereof and solves the problem that the application of the conventional polyaryletherketone resin is limited because of limited heat resistance. The repeating structural unit of the polyaryletherketone resin disclosed by the invention is shown in the description. The weight-average molecular weight of the unit is 20,000 to 75,000. In the formula of the unit, R may be methyl, ethyl, n-butyl, isobutyl, n-hexyl, trifluoromethyl, epoxypropyl, propenyl, propinyl, phenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 4-vinylphenyl, 4-alkynylphenyl or 4-cyanophenyl; R1, R2, R3 and R4 are H, Br, I, C1-C6 branched alkyl or C1-C6 linear alkyl; and Ar is a residue obtained by removing dihydroxy from bisphenol monomer. The glass transition temperature of the polyaryletherketone resin with the carbazole ring in the main chain, which is prepared by the method, may be up to 293 DEG C, and the intrinsic viscosity of the resin is proper, the solubility and processability, as well as toughness and mechanical properties of the resin are high. Thus, the resin has a wide application range.

Description

technical field [0001] The invention relates to a polyaryletherketone resin with a main chain containing a carbazole ring structure and a preparation method thereof, belonging to the field of polymer materials. Background technique [0002] As a thermoplastic engineering plastic with special structure, polyaryletherketone has excellent mechanical properties, solvent resistance, chemical corrosion resistance, radiation resistance and flame retardancy. Since the commercialization of PEEK resin was launched by ICI in the 1970s, in order to further expand the application field of polyaryletherketone resin, researchers have tried to modify it from many aspects. Among them, polyaryletherketone resin's High temperature resistance and solubility are one of the fields that have been studied more. [0003] Chinese patent CN85108751 discloses amorphous polyaryletherketone (PEK-C) prepared by polycondensation of phenolphthalein bisphenol monomer and 4,4'-dihalobenzophenone monomer, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/40
Inventor 周光远王菲菲王红华王志鹏
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI