Polyvinylene sulfide and preparation method thereof

A polyvinylene and sulfide technology, which is applied in the fields of polymer chemistry and material science, can solve the problems of increasing the cost of synthetic routes and limiting application fields, and achieves the effects of excellent space selection, simple process, and easy operation

Inactive Publication Date: 2013-12-25
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, expensive transition metal catalysts increase the cost of this synthetic route, and residual toxic metals in the polymer greatly limit the application fields of such polymers.

Method used

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  • Polyvinylene sulfide and preparation method thereof
  • Polyvinylene sulfide and preparation method thereof
  • Polyvinylene sulfide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] (1) Synthesis of the first monomer binary alkynyl compound 1a

[0059] Add 1.694g (7.4mmol) of bisphenol A, 4.081g (16.3mmol) of 1-bromo-4-benzylbromobenzene and 2.557g (18.5mmol) of potassium carbonate in a 250mL single-necked flask, add 60mL of acetone, and heat to reflux for 7 hours. After cooling, filtering, and spin-drying, the obtained crude product was purified by thin-layer chromatography and dried in vacuo to obtain 4.128 g of white solid (98.5% yield), which was the first intermediate. 1 H NMR (400MHz, CDCl 3 ),δ(TMS,ppm):7.50(d,4H,Ar-H),7.30(d,4H,Ar-H),7.14(d,4H,Ar-H),6.85(d,4H,Ar-H) H),4.99(s,4H,CH 2 ),1.64(s,6H,CH 3 CCH 3 ).

[0060] Take the first intermediate 3.964g (7mmol), PdCl in the glove box 2 (PPh 3 ) 2 197mg (0.28mmol), CuI107mg (0.56mmol), PPh 3 Add 220mg (0.84mmol) into a 250mL single-necked flask, add 100mL of mixed solvent tetrahydrofuran / triethylamine / piperidine (volume ratio: 60:30:10), after all dissolve, add 3.0mL (21mmol) of trime...

Embodiment 2～5

[0071] Examples 2-5 investigated the influence of different temperatures on reaction conditions. The preparation of polymerized monomers was the same as in Example 1. The reaction conditions and results of step (3) are shown in Table 1.

[0072] Table 1 Effect of Temperature on the Polymerization of Monomers 1a and 2a a

[0073]

[0074] a Reaction in THF under nitrogen atmosphere for 4 hours; [M 0 ]=50mM.

[0075] b T = reaction temperature.

[0076] c Solubility (S) tested in common organic solvents such as THF, chloroform and DMF: √=completely soluble; Δ=partially soluble.

[0077] d Determined by GPC with linear polystyrene as calibrator and THF as mobile phase.

Embodiment 6～9

[0079] Examples 6-9 investigated the influence of different solvents on the reaction conditions. The preparation of polymerized monomers was the same as in Example 1. The reaction conditions and results of step (3) are shown in Table 2.

[0080] Table 2 The influence of solvent on the polymerization of monomer 1a and 2a a

[0081]

[0082] a Reaction under nitrogen atmosphere; T=30℃; [M 0 ]=50mM.

[0083] b t = reaction time.

[0084] c Solubility (S) tested in common organic solvents such as THF, chloroform and DMF: √=completely soluble; Δ=partially soluble.

[0085] d Determined by GPC with linear polystyrene as calibrator and THF as mobile phase.

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Abstract

The invention discloses a preparation method of polyvinylene sulfide. The preparation method comprises the following step of performing click polymerization reaction on a binary alkynyl compound and a binary mercapto-compound in an organic solvent to obtain the polyvinylene sulfide. The obtained polyvinylene sulfide comprises an internal unit shown in a formula (I), the step of polymerization is shown in a formula (IV), wherein n is more than 1 and is selected from organic groups. The preparation method does not need heating or any catalyst, is simple and efficient in process, and has excellent space selectivity. The invention also discloses the polyvinylene sulfide obtained through the preparation method, and the polyvinylene sulfide has good workability and film-forming property, high heat stability and refractive index and aggregation induced luminescent property.

Description

technical field [0001] The invention relates to the fields of polymer chemistry and material science, in particular to a polyethylene sulfide and a preparation method thereof. Background technique [0002] Polyvinyl sulfide is a unique class of sulfur-containing macromolecules, which have excellent photoelectric properties and are widely used in optical devices. However, there are many problems in the synthesis of polyvinyl sulfides, such as reactivity, difficult preparation of monomers, complicated polymerization process, etc. Therefore, it is of great significance to develop simple and efficient synthetic methods. [0003] In the 1950s, William E.Truce and John A.Simms discovered the nucleophilic addition reaction between aromatic alkyne and alkyl alkyne and sodium thiolate, and successfully synthesized vinyl sulfide (J.Am.Chem.Soc ., 1956, 12, 2756-2759), this reaction is named as "hydrosulfhydration of alkynes". In the past two decades, this reaction has been fully de...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G75/04C08G75/045
Inventor 姚必成秦安军唐本忠孙景志
Owner ZHEJIANG UNIV
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