Sulfamide polymer and preparation method thereof

A technology for sulfonamides and polymers, applied in the field of sulfonamide polymers and their preparation, can solve the problems of low molecular weight of polymer products, high cost of raw materials, low reaction yield and the like, and achieves simple and convenient operation, low cost, and high reaction Efficient effect

Active Publication Date: 2021-07-13
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with polyamide polymer materials that have been widely used in the fields of engineering plastics and membrane materials, the synthesis of sulfonamide polymers has low reaction yield, many side reactions, expensive raw material costs, and low molecular weight of polymerization products. Insufficient, its development is relatively slow

Method used

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  • Sulfamide polymer and preparation method thereof
  • Sulfamide polymer and preparation method thereof
  • Sulfamide polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] A kind of sulfonamide polymer P1 of the present embodiment (in general formula (I) when R 1 is diphenyl ether, R 2 When being 9,9-dihexylfluorene), its structural formula is as follows:

[0044]

[0045] The sulfonamide polymer P1 is prepared from binary azide monomer and binary boronic acid monomer through a two-component reaction, and its reaction equation is shown in reaction formula (1):

[0046]

[0047] In this example, the synthesis method of monomer M1 can refer to published literature (Alan R. Katritzky, James W. Rogers, Rachel M. Witek, et al. Journal of Energetic Materials, 2007, 25 (2): 79-109. ) synthetic method; M2 is 9,9-dihexylfluorene-2,7-diboronic acid and the catalyst cuprous chloride can be purchased from the market.

[0048] The preparation steps of described sulfonamide polymer are as follows:

[0049] Add 0.0761g (0.2mmol) monomer M1, 0.0844g (0.2mmol) monomer M2, and 0.004g (0.04mmol) catalyst CuCl to a 10mL Schlenk reaction tube, inject 2...

Embodiment 2

[0055] A kind of sulfonamide polymer P2 of the present embodiment (in general formula (I) when R 1 is diphenyl ether, R 2 When being phenyl), its structural formula is as follows:

[0056]

[0057] The sulfonamide polymer P2 is prepared from binary azide monomers and binary boronic acid monomers through a two-component reaction, and its reaction equation is shown in reaction formula (2):

[0058]

[0059] In this example, the synthesis method of monomer M1 is the same as in Example 1; M3 is 1,4-benzenediboronic acid.

[0060] The preparation steps of described sulfonamide polymer are as follows:

[0061] In the 10mL Schlenk reaction tube, add 0.0761g (0.2mmol) monomer M1, 0.0332g (0.2mmol) monomer M3, and 0.004g (0.04mmol) catalyst CuCl, inject 2mL of methanol solvent along the bottle wall with a syringe; Cover the mouth of the reaction tube with an air extraction joint, and the joint is connected to the air, and the valve of the reaction tube is adjusted to communica...

Embodiment 3

[0066] This example is a sulfonamide model compound M10 mentioned in Example 1, and its structural formula is as follows:

[0067]

[0068] The sulfonamide model compound M10 is prepared by reacting boric acid monomers and azide compounds, which is the first synthesis of the present invention, and its reaction equation is shown in Reaction Formula (3):

[0069]

[0070] Wherein M2 is 9,9-dihexylfluorene-2,7-diboronic acid, which can be purchased from the market, and this example is purchased from Shanghai Bid Medical Technology Co., Ltd.; the synthetic method of M3 can refer to published literature (Jingjing Shi, Bing Zhou, YaxiYanga, Yuanchao Li.Organic&Biomolecular Chemistry, 2012,10(45):8953-8955.) The synthetic method obtains; The catalyst cuprous chloride can be purchased from the market, and this example is purchased from Japan TCI company.

[0071] The preparation steps of the described sulfonamide model compound M10 are as follows:

[0072] Add 0.3378g (0.8mmol)...

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Abstract

The invention discloses a sulfamide polymer and a preparation method thereof, and relates to the technical field of polymer synthesis. The sulfamide polymer has a structural formula as shown in a general formula (I), wherein R1 and R2 are organic groups, and n is the degree of polymerization and is an integer between 2 and 50. The preparation method comprises the following steps: carrying out polymerization reaction on a binary sulfonyl azido compound and a binary arylboronic acid compound in an organic solvent, and carrying out precipitation separation on the product through diethyl ether to obtain the sulfamide polymer, wherein any alkali, ligand or additive is not needed. The method has the advantages of mild reaction conditions, simple reaction post-treatment, cheap and low-toxicity catalyst, easy substrate modification and the like.

Description

technical field [0001] The invention belongs to the technical field of polymer synthesis, and in particular relates to a sulfonamide polymer and a preparation method thereof. [0002] technical background [0003] Sulfonamide compounds have high application value in many fields such as organic synthesis, biomedicine, dyes, and pesticides. Sulfonamide polymers are a class of polymer materials containing sulfone amide repeating units in the main chain, which have excellent thermal stability, corrosion resistance, processability and mechanical properties. The traditional synthetic method of sulfonamide polymer adopts dibasic sulfonyl chloride and diamine to polymerize as monomer, and needs to add appropriate excess diamine monomer or other organic base, inorganic base as acid-binding agent (S.A.Sundet, W.A.Murphey , S.B.Speck.Interfacial polycondensation.IX.Polysulfonamides.Polymer Chemistry, 1959,40(137):389-397), (Yoshio Imai; Mitsuru Ueda, Itsuru Ueda, and Takashi Iizawa.Syn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G75/30
CPCC08G75/30
Inventor 曹德榕张可怡黄汉初
Owner SOUTH CHINA UNIV OF TECH
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