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Amido bond phenylboronic acid ester-containing polyether sulphone polymer and preparation method thereof

A technology of bond phenyl boronate and polyaryl ether sulfone is applied in the field of amide bond-containing phenyl boronate polyaryl ether sulfone polymer and its preparation, which can solve the problem that the position and content of boron-containing polymer cannot be introduced, and achieves The method is simple and easy to implement, the grafting rate is high, and the effect of excellent high temperature ablation resistance

Inactive Publication Date: 2015-02-04
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Tae Soo Jo et al. published an article in J.AM.CHEM.SOC. in 2009 using an Ir catalyst to catalyze the reaction of biboronic acid pinacol ester with polyether ether sulfone to obtain a polyarylether sulfone material containing borate in the main chain , but the boron-introduced position and content of the boron-containing polymer obtained by this method cannot be introduced into the polyarylethersulfone polymer according to the molecular design method

Method used

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  • Amido bond phenylboronic acid ester-containing polyether sulphone polymer and preparation method thereof
  • Amido bond phenylboronic acid ester-containing polyether sulphone polymer and preparation method thereof
  • Amido bond phenylboronic acid ester-containing polyether sulphone polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Preparation of polyarylethersulfone containing p-aminophenyl side groups (1)

[0047] 5.4597g (0.027mol) 4,4`-dihydroxydiphenyl ether, 0.6037g (0.003mol) 2-(4`-aminophenyl)-1,4-hydroquinone monomer, 7.6275g (0.03 mol) 4,4`-difluorodiphenylsulfone monomer and 4.5603g of anhydrous potassium carbonate, 57mL of sulfolane, 20mL of toluene, put into a three-necked flask equipped with a nitrogen hole, mechanical stirring and a water device, and nitrogen , start stirring, heat up to the reflux of the azeotropic dehydrating agent, react for 2 hours, remove the azeotropic dehydrating agent, heat up to 170°C and continue the reaction for 8 hours; then the obtained polymer solution is precipitated in deionized water, pulverized, washed , and dried to obtain 12 g off-white polyarylethersulfone polymer powder containing p-aminophenyl side groups.

[0048] The molecular formula is as follows,

[0049]

[0050] where n is 14.

Embodiment 2

[0051] Example 2: Amidation reaction of polyarylethersulfone containing p-aminobenzene side groups and p-carboxyphenylboronic acid pinacol ester to prepare polyarylethersulfone material containing amide bond phenylboronic acid ester (1)

[0052] Put 4.16g of polyaryl ether sulfone containing p-aminophenyl side groups and 0.27g of p-carboxyphenylboronic acid pinacol ester (1.1 times the molar weight of amino groups in polyaryl ether sulfone containing aminophenyl side groups) into a stirring Add 0.31g of N,N-dicyclohexyldiimine (DCC) (1.5 times the molar amount of amino groups in polyarylethersulfone containing aminophenyl side groups), 0.18g of 4-dimethylaminopyridine (DMAP) (0.15 times the molar weight of amino groups in polyarylethersulfone containing aminobenzene side groups), then vacuumize and release high-purity nitrogen, then vacuumize and release high-purity nitrogen, repeat 4 times, and finally inject 100mL tetrahydrofuran to dissolve, and then Seal, start and stir, a...

Embodiment 3

[0053] Example 3: Preparation of polyarylethersulfone containing p-aminobenzene side groups (2)

[0054] 4.2464g (0.009mol) 4,4`-dihydroxydiphenyl ether, 1.8110g (0.021mol) 2-(4`-aminophenyl)-1,4-hydroquinone monomer, 7.6275g (0.03 mol) 4,4`-difluorodiphenyl sulfone monomer and 4.5603g of anhydrous potassium carbonate, 55ml of sulfolane, and 12mL of toluene were placed in a three-necked flask equipped with a nitrogen through hole, mechanical stirring and a water device, and nitrogen was passed. Start stirring, heat up to the reflux of the azeotropic dehydrating agent, react for 2 hours, get rid of the azeotropic dehydrating agent, heat up to 170°C and continue the reaction for 8 hours; then the obtained polymer solution is precipitated in deionized water, pulverized, washed, After drying, 13 g of off-white polyarylethersulfone polymer powder with p-aminophenyl side groups was obtained.

[0055] The molecular formula is as follows:

[0056]

[0057] where n=13.

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Abstract

The invention relates to an amido bond phenylboronic acid ester-containing polyether sulphone polymer and a preparation method thereof, belonging to the technical field of macromolecular materials. The amido bond-containing phenylboronic acid ester polyether sulphone polymer is of a polymer with a polyether sulphone main chain and an amido bond phenylboronic acid ester-containing side chain. The preparation method comprises the steps of: firstly, synthesizing amino-benzene side group-containing polyether sulphone, then performing an amidation reaction on the amino-benzene side group-containing polyether sulphone and carboxyl phenylboronic acid pinacol ester, and carrying out acetone treatment to obtain the amido bond phenylboronic acid ester-containing polyether sulphone material. The phenylboronic acid ester can be quantitatively introduced into the polyether sulphone main chain by adopting an amidation method, thus having potential applications to aspects of catalysis, inorganic material blend polymer composites, flame retardance and the like; in addition, the phenylboronic acid ester is an important reaction intermediate in organic synthesis, and therefore, the amido bond phenylboronic acid ester-containing polyether sulphone is an important reaction intermediate in functionalized polymer synthesis, thus having potential applications on the aspects of preparing luminescent materials, sensing materials and the like.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to an amide bond-containing phenyl borate polyaryl ether sulfone polymer and a preparation method thereof. Background technique [0002] Due to its excellent thermal and chemical stability, aromatic backbone polyarylethersulfone is still an important special engineering plastic. Introducing functional groups into the main chain of aromatic polymers can lead to special functions, enhanced performance and wider potential applications. In recent years, functionalized polyarylethersulfone has been made into a variety of membrane materials, such as ion permeation membranes, gas separation membranes, proton exchange membranes for fuel cells, and so on. [0003] Akira Suzuki, Richard Heck, and Hideo Negishi jointly won the 2010 Nobel Prize in Chemistry for their significant contributions to the Suzuki-Miyaura reaction. The Suzuki-Miyaura reaction has strong substrate...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G75/23C07C317/22C07C315/04C07F5/02
Inventor 姜振华王永鹏张海博刘韬崔曾多商赢双
Owner JILIN UNIV
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