Method for synthesizing polythioether

A synthesis method and technology of polythioether, applied in the field of polythioether polymers, can solve the problems of toxic polymer degradation reactions, etc., and achieve the effect of simple and easy preparation method and strong practicability

Active Publication Date: 2017-11-03
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the use of transition metal complex catalysts has certain drawbacks
For example, the prepared polymer materials may be toxic or cause polymer degradation reactions due to metal residues, limiting their applications in biomedicine and other fields

Method used

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  • Method for synthesizing polythioether
  • Method for synthesizing polythioether
  • Method for synthesizing polythioether

Examples

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Effect test

Embodiment 1

[0016] Example 1, the stepwise addition reaction of 1,4-xylylene mercaptan and diethylene glycol divinyl ether catalyzed by p-methoxybenzaldehyde (wherein the molar ratio of the two monomers is 1:1)

[0017] Add diethylene glycol divinyl ether (1.44g), 1,4-benzenedimethyl mercaptan (1.56g), anisole solution (3g), p-methoxybenzaldehyde ( 0.249g), filled with argon gas after refrigerated pumping to remove oxygen, and stirred at room temperature to make the reaction between two 23W compact energy-saving lamps (that is, the light source is in the wavelength range of 420nm, and the light intensity is 600~1000μWcm -2 ) under irradiation conditions. The polymer molecular weight increases linearly with time ( figure 1 ). After 4 hours of reaction, the monomer conversion rate reached 89%, and the polymer product M n =9600 g / mol, PDI = 1.78.

Embodiment 2

[0020] Embodiment two, the photopolymerization reaction of 1,4-xylylene mercaptan and diethylene glycol divinyl ether catalyzed by p-methoxybenzaldehyde (wherein 1,4-xylylene mercaptan is excessive)

[0021] Add diethylene glycol divinyl ether (1.10g), 1,4-benzenedimethyl mercaptan (1.90g), anisole solvent (3g), p-methoxybenzaldehyde ( 0.124g). Refer to Example 1 for other operations (i.e., charge into argon gas after deoxygenation by freezing and pumping, stir at room temperature, and make the reaction in two 23W compact energy-saving lamps (light source 420nm wavelength range, light intensity is 600~1000μW cm -2 ) under the irradiation conditions, and the following examples omit the description and are all the same). After 7 hours of reaction, the monomer conversion rate reached 71%, and the polymer product M n = 4200 g / mol, PDI = 1.20. Proton NMR spectrum ( figure 2 ) showed that the reaction produced a narrow distribution of α, ω-dithiol-terminated telechelic polymers...

Embodiment 3

[0022] Embodiment three, the photopolymerization reaction of the mercapto-terminated telechelic polymer and diethylene glycol divinyl ether catalyzed by p-methoxybenzaldehyde

[0023] In a 25mL round-bottomed flask, add α,ω-dithiol-terminated oligomers (M n =4200g / mol, PDI=1.20), diethylene glycol divinyl ether, p-methoxybenzaldehyde (0.249g), anisole solvent (3g). The molar ratio of the telechelic polymer to the diethylene glycol divinyl ether monomer is 1:1, and the total concentration of the two monomers in the solvent is 50%. Refer to Embodiment 1 for other operations. After 12 hours of reaction, the monomer conversion rate reached 87%, and the polymer product M n = 16200 g / mol, PDI = 1.79. It is proved that the telechelic polymer is still active, and can continue to carry out addition reaction with divinyl monomer under the action of catalyst.

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Abstract

The invention discloses a method for synthesizing polythioether, particularly relates to a mercapto-ene photopolymerization system using a benzaldehyde derivative as a catalyst. The method comprises the step of synthesizing the polythioether by taking alpha,omega-dimercapto compound and alpha,omega-divinyl ether as a monomer. The method has the advantages that visible lights (such as a household 23W energy-saving lamp) can be used as a light source with an inexpensive benzaldehyde compound as a catalyst, and the stepwise addition polymerization reaction of mercapto-ene can be realized at room temperature. Moreover, alpha,omega-dimercapto-terminated telechelic polymers can be prepared by controlling the reaction monomer ratio. In addition, the telechelic polymers still retain characteristics of living polymerization, can continue to conduct addiction reaction with divinyl monomers under the action of the catalyst. The method for synthesizing the polythioether has mild reaction conditions, a wide application range, colorless/odorless performance (without post-treatment to the product) and high reaction speed.

Description

technical field [0001] The invention relates to a mercapto-alkene visible light photopolymerization system under the action of a benzaldehyde derivative catalyst, in particular to using a substituent-containing benzaldehyde derivative as an organic catalyst to promote the synthesis of dimercapto monomers and dithiol monomers at room temperature. Stepwise addition polymerization of vinyl ether monomers and preparation of polythioether polymers with telechelic functional groups. Background technique [0002] Compared with the traditional photopolymerization of vinyl monomers, mercapto-ene polymerization has obvious advantages in terms of polymerization process and polymer properties. For example, mercapto-ene polymerization has low polymerization shrinkage, wide range of raw materials, etc. More importantly, thiol-ene polymerization can be effectively combined with click chemistry. Therefore, this type of polymerization reaction has attracted extensive attention in the indus...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G75/045
Inventor 马育红毕舜超高超张文秀马文超张先宏杨万泰
Owner BEIJING UNIV OF CHEM TECH
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