Macrocyclic aryl thioether ether sulfone oligomer and preparation method thereof

A technology of oligomer and polysulfoxide, which is applied in the field of synthesis and preparation of aromatic cyclic polysulfoxide oligomer, can solve the problem of high cost and achieve the effects of low cost, wide sources and mild reaction conditions

Inactive Publication Date: 2009-09-02
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method for preparing cyclic sulfoxide oligomers has the disadvantages of high cost, using expensive fluorine-containing monomer as the starting reactant, and the reaction is carried out at high temperature.

Method used

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  • Macrocyclic aryl thioether ether sulfone oligomer and preparation method thereof
  • Macrocyclic aryl thioether ether sulfone oligomer and preparation method thereof
  • Macrocyclic aryl thioether ether sulfone oligomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 Preparation of polyether ketone ether sulfoxide cyclic oligomer

[0044] Place 6.68g (0.05mol) of anhydrous aluminum trichloride and 500mL of carbon disulfide in a 1000mL three-neck flask with a nitrogen inlet, a spherical condenser connected to a calcium chloride drying tube and a gas absorption device at the top. 2.3821 g (0.02 mol) of thionyl chloride and 7.3258 g (0.02 mol) of 4,4'-phenoxybenzophenone were dissolved in 80 mL of carbon disulfide. Dry nitrogen gas was introduced, and the solution was slowly and uniformly dropped into the three-necked flask within 8 hours under room temperature and vigorous stirring. After the dropwise addition was completed, the stirring was continued for 3 hours, and 150 mL of 0.1M dilute hydrochloric acid was added to terminate the reaction. After the organic phase was obtained by liquid separation, it was washed three times with 100 mL of distilled water to remove the catalyst. Under the protection of nitrogen, it was co...

Embodiment 2

[0045] Example 2 Preparation of Polyetherethersulfoxide Cyclic Oligomer

[0046] The reaction monomer 5.2442g (0.02mol) triphenyl ether was substituted for 4,4'-phenoxybenzophenone, and other monomer feed ratios, reaction conditions and processing steps were the same as in Example 1 to obtain light yellow powder with a yield of was 76%. The main signal peaks of the laser mass spectrogram of the product are located at: m / z=617.2, 925.3, 1233.8, 1541.8, 1850.0, 2158.3, respectively corresponding to the protonated molecular ions of the dimer to the heptamer of the cyclic oligomer peaks, indicating that the product is composed of a series of cyclic oligomers with different degrees of polymerization.

Embodiment 3

[0047] Example 3 Preparation of methyl polyether ketone ether sulfoxide cyclic oligomer

[0048] The reaction monomer 7.8820g (0.02mol) 4,4'-(3-methyl)phenoxy-benzophenone is replaced by 4,4'-phenoxybenzophenone, other monomer feed ratios and reaction conditions are the same as The processing steps were the same as in Example 1 to obtain a cyclic oligomer with a yield of 90%. The main signal peaks of the laser mass spectrogram of the product are located at: m / z=881.4, 1321.6, 1761.8, 2201.8, 2641.9, 3082.4, 3522.3, respectively corresponding to the protonation of the dimer to the octamer of the cyclic oligomer Molecular ion peaks, indicating that the product is composed of a series of cyclic oligomers with different degrees of polymerization.

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Abstract

The invention relates to a macrocyclic aryl thioether ether sulfone oligomer and preparation method thereof. Under 'pseudo-high dilution' condition, Friedel-Crafts-Karrer reaction is utilized to open up a new route of taking thionyl chloride and substituted aromatic hydrocarbon monomers as basic raw materials to synthesize a macrocylic oligomer of high-performance resin, namely the macrocyclic aryl thioether ether sulfone oligomer with high yield. Under the action of tetrabutylammonium iodide and oxalyl chloride, sulfoxide groups of the macrocyclic aryl thioether ether sulfone oligomer can be reduced into thioether bonds to generate a cyclic polythioether oligomer. The cyclic polythioether oligomer can be melted and subjected to ring opening polymerization under the initiation of a free radical initiator to obtain a high-performance linear arylene sulfide by using a cyclic structure and low melt viscosity peculiar to the aromatic ring-shaped oligomer. Products subjected to ring opening polymerization do not contain ions and can be widely applied in the fields of micro-electronics, high temperature resisting viscose agents, and the like requiring excellent electrical insulating property.

Description

Technical field: [0001] The invention belongs to the synthesis and preparation method of aromatic ring polysulfoxide oligomer. Background technique: [0002] The synthesis of aromatic cyclic oligomers is a research field developed in the late 1980s in response to the demand for advanced composite materials in high-tech fields such as modern aerospace, aviation, microelectronics, and machinery. The unique ring structure and low melt viscosity of aromatic ring oligomers, under the triggering of initiators, can quickly carry out controllable ring-opening polymerization and no small molecule by-products are generated during the polymerization process, which determines its preparation. High-performance composite materials, high temperature resistant adhesives and other fields have important application value. [0003] At present, among the high-performance polymers that have been commercialized, linear aromatic polyethers and polysulfides occupy an important position, especially...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D327/00C08G75/06
Inventor 郭庆中吴江渝鄢国平李亮喻湘华程志毓杜飞鹏
Owner WUHAN INSTITUTE OF TECHNOLOGY
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