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Process for the preparation of amide bond-linked polymers

A technology of polymers and amide bonds, applied in the field of polymer chemistry, can solve problems such as restrictions on monomer types, harsh reaction conditions, and application restrictions, and achieve the effects of wide application range, easy handling, and fast reaction rate

Active Publication Date: 2021-01-26
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the anionic polymerization system is simple, the reaction conditions are very harsh, the system is sensitive to water and oxygen, and it is usually operated under high vacuum conditions, so its application is limited.
The controllable free radical methods such as ATRP and RAFT have the advantages of simple polymerization system, wide application range of monomers, and strong molecular design ability, but there are still certain restrictions on the types of monomers.

Method used

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  • Process for the preparation of amide bond-linked polymers
  • Process for the preparation of amide bond-linked polymers
  • Process for the preparation of amide bond-linked polymers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] (1) Add 6.1g (152mmol) of sodium hydroxide, 7.9g (100mmol) of selenium powder and 250mL of N,N'-dimethylformamide solvent into a 500mL three-necked flask and stir under ventilation , then slowly added 4.9g of hydrazine hydrate into the system, and then reacted at room temperature for 2h. Subsequently, 15.8 g (100 mmol) of 2-bromopyridine was slowly added dropwise into the reaction flask, and then the temperature was raised to 120° C. for 24 h, and then returned to room temperature after stopping the reaction. Suction filtration, and the filtrate was extracted with a large amount of ethyl acetate. The organic phase was washed once with saturated ammonium chloride solution and deionized water and saturated brine respectively, then stirred and dried with anhydrous sodium sulfate for 2 hours, concentrated to obtain a crude product, and purified by column chromatography. Finally, 9.7 g of the final product PySeSePy was obtained with a yield of 62%. The route of the above r...

Embodiment 2

[0098] (1) In a 50mL reaction tube, add 0.3840g (0.192mmol) of the terminal azidated polyethylene glycol monomethyl ether PEG1900-N prepared in Example 1 3 , 0.0565g (0.18mmol) of bispyridine diselenide PySeSePy and 0.0128g (0.06mmol) of trimesic acid were stirred and passed into an inert gas, and then the temperature was 2.8mL of a toluene solution of trimethylphosphine at 0°C Slowly inject into the system, when no gas is generated in the system, the temperature of the system is raised to 40°C, and the reaction is continued for 24 hours under ventilation. After the reaction stopped, add an appropriate amount of tetrahydrofuran to dilute, then add dropwise to cold anhydrous ether for precipitation, let stand, filter with suction, and dry in a vacuum box to obtain 0.3875g of terminal azide coupled with trimesic acid. The three-arm polymer formed by the polyethylene glycol monomethyl ether has a yield of 99.0%. The reaction scheme is as follows:

[0099]

[0100] Figure 7...

Embodiment 3

[0103] (1) 18.88g (147.3mmol) of tert-butyl acrylate, 0.3175g (2.2130mmol) of CuBr, 0.0247g (0.1106mmol) of CuBr 2 , 0.4026g (2.3230mmol) of PMDETA (N,N,N',N',N"-pentamethyldiethylenetriamine), 0.7391g (4.4260mmol) of 2-bromopropionic acid methyl ester (MBrP) and Add 20mL of dimethyl sulfoxide into a 50mL Schlenk bottle, then pump and inflate 3 times, and put it in an oil bath at 60°C for 3h. After quenching the reaction, dissolve the product with tetrahydrofuran, and pass Neutral alumina column was used to remove copper salt, precipitated in a mixed solvent of methanol and water, filtered with suction, and dried in a vacuum oven for 24 hours to finally obtain 11.5 g of tert-butyl polyacrylate (named as PtBA-Br), with a yield of 58.6% , and the number average molecular weight M measured by gel permeation chromatography (GPC) n = 5000 Da, molecular weight distribution PDI = 1.17.

[0104] (2) 6g (1.2mmol) of PtBA-Br, 1.5602g (24mmol) of NaN 3 and 30mL of DMF were added to a ...

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Abstract

The invention relates to a preparation method of a polymer linked by an amide bond, comprising the following steps: uniformly mixing a polymer having an azide group at one end, a carboxyl-containing compound, and a catalyst bispyridine diselenide (PySeSePy) at 0-5 Trimethylphosphine (Me 3 The organic solution of P) is reacted, when the reaction does not produce bubbles, then react at 25-40°C for 2-24h to obtain a polymer connected by an amide bond, wherein the carboxyl-containing compound is a dibasic carboxylic acid, a polycarboxylic acid, A polymer with a carboxyl group at one end or a polymer with a carboxyl group at both ends; the molar ratio between the polymer with an azide group, bispyridine diselenide, carboxyl-containing compound and trimethylphosphine is 0.9‑2.2:1 ‑2: 1‑2: 20‑40. In the present invention, the Staudingers-Vilarrasa reaction catalyzed by bispyridine diselenide is used for the connection between polymers, and an amide bond is formed through the reaction between a carboxyl compound and a polymer with an azide group at one end, thereby preparing the A polymer linked by amide linkages.

Description

technical field [0001] The invention relates to the field of macromolecular chemistry, in particular to a method for preparing a polymer linked by an amide bond. Background technique [0002] Block polymers have very good application prospects in the fields of nano-devices and biomedicine, and more and more researchers are working on the synthesis of block polymers. With the development of high-efficiency reactions such as ATRP and controlled radical polymerization and click chemistry, more and more types of block polymers can be prepared, such as block polymers that respond to temperature, light, pH, and magnetism. [0003] At present, the synthesis methods of block polymers mainly include living anionic polymerization, living free radical polymerization, efficient click reaction and controllable free radical polymerization methods such as ATRP and RAFT. Although the anionic polymerization system is simple, the reaction conditions are very harsh, the system is sensitive to...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/332C08G65/333C08G65/334C08G81/02C08F8/30C08F120/18C08G65/331
CPCC08F8/30C08G65/331C08G65/3326C08G65/333C08G65/3346C08G81/025C08G2650/10C08F120/18
Inventor 张伟赵肖宁朱秀林潘向强周年琛张正彪朱健
Owner SUZHOU UNIV
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