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Styrene monomer containing alkyl sodium (potassium) thiosulfate and preparation method thereof

A technology of alkyl sodium thiosulfate and sodium thiosulfate, applied in the field of organic synthesis and polymers, can solve the problem that mercapto groups and polymerizable monomers cannot exist stably at the same time, and achieve simple structure, strong operability, and easy Preparing the effect of preservation

Inactive Publication Date: 2009-09-23
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because thiol and polymerizable double bonds are highly reactive, thiol and polymerizable monomers cannot exist stably at the same time

Method used

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  • Styrene monomer containing alkyl sodium (potassium) thiosulfate and preparation method thereof
  • Styrene monomer containing alkyl sodium (potassium) thiosulfate and preparation method thereof
  • Styrene monomer containing alkyl sodium (potassium) thiosulfate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 3.00g of PEO400, 24.817g (0.1mol) of sodium thiosulfate and 30mL of water into a 250mL round bottom flask equipped with a magnetic stirring bar, and stir well. Add 20.349g (0.12mol) p-chloromethylstyrene (mass fraction 90%) and 10mL ethanol to a 50mL beaker, stir well and pour into a constant pressure funnel, then drop it into a 250mL round bottom flask. The reaction was stopped after 6 hours at room temperature. Use a rotary evaporator to spin off ethanol and part of the water to obtain a solid. The solid was collected by suction filtration and rinsed with a small amount of cold water and petroleum ether to remove unreacted p-chloromethylstyrene, sodium thiosulfate and PEO400 to obtain a pure product—(4-vinyl)-benzyl sodium thiosulfate , the structural formula is as follows:

[0025]

Embodiment 2

[0027] Add 10.00 g (0.18 mol) of potassium hydroxide, 9.896 g (0.1 mol) of 1,2-dichloroethane and 40 mL of absolute ethanol into a 250 mL three-neck flask equipped with a magnetic stirring bar, and stir evenly. Add 12.015g (0.1mol) 4-hydroxystyrene and 20mL absolute ethanol to a 50mL beaker, stir well and pour into a constant pressure funnel, install a spherical condenser and a constant pressure funnel on a 250mL three-necked bottle, and heat After reaching the reflux temperature, drop liquid, stop the reaction after reacting for 14 hours, remove the generated salt by filtration, and obtain the etherified product. Use a rotary evaporator to spin off half of the solvent at room temperature for later use.

[0028] Add 3.00g of PEO 400, 30.00g (0.12mol) of sodium thiosulfate and 30mL of water into a 250mL round bottom flask equipped with a magnetic stirring bar, and stir evenly. Pour the ethanol solution of the synthesized etherified product into a constant pressure funnel, and ...

Embodiment 3

[0031] Put a magnetic stirring bar into a 250mL three-necked flask equipped with a spherical condenser, add 11.916g (0.1mol) 4-aminostyrene, 9.896g (0.1mol) 1,2-dichloroethane, 15.178g (0.15 mol) triethylamine and 70 mL of absolute ethanol, heated to reflux temperature and reacted for 8 hours to stop the reaction, and filtered to remove the generated salt to obtain a nucleophilic substitution product. Use a rotary evaporator to spin off half of the solvent at room temperature for later use.

[0032] Add 3.00g of PEO400, 30.00g (0.12mol) of sodium thiosulfate and 30mL of water into a 250mL round bottom flask equipped with a magnetic stirrer, and stir evenly. Pour the ethanol solution of the synthesized nucleophilic substitution product into a constant pressure funnel, and then drop it into a 250mL round bottom flask. The reaction was stopped after 6 hours at room temperature. The ethanol was spun off with a rotary evaporator to obtain a solid. The solid was collected by suct...

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Abstract

The invention relates to a styrene monomer containing alkyl sodium (potassium) thiosulfate and a preparation method thereof, belonging to the technical field of organic synthesis and high polymer. In the invention, styrene based compound containing halogenated methylene is used as raw materials, methanol or ethanol and water are used as mixed solvent, PEO400 is used as a phase transfer catalyst, the halogen on the halogenated methylene reacts with the Bunte Salts of excessive saturated sodium (potassium) thiosulfate and is stirred to react under the room temperature till the sodium (potassium) thiosulfate raw material is totally consumed, then the methanol or ethanol and part of water are removed from the mixture by pressure reduction, is cooled and crystallized and then carried out the pumping filtration and collection to obtain solid; and the solid is leached (eluted) sequentially by little cooling water and petroleum ether and dried under the temperature of 40 DEG C to obtain the monomer, the monomer releases active sulfhydryl-groups with the function of chain transfer under the action of strong polarity reagents or diluted acid such as DMSO, DMF, and the like to form an AB monomer containing polymerizable double bond as well as active sulfhydral-groups. The AB monomer has simple structure, is easily prepared and stored, and is expected to be applied to super branched polymer prepared by a sulfhydryl-group chain transfer super branched polymerization method.

Description

technical field [0001] The invention relates to a styrene monomer containing alkylthiosulfate sodium (potassium) salt and a preparation method thereof, belonging to the technical fields of organic synthesis and macromolecule. Background technique [0002] The molecular design of polymerizable monomers plays a pivotal role in organic synthesis and polymer preparation. By introducing functional groups into polymerizable monomers, the monomers and polymers can be endowed with various special functions. Mercapto compounds have special properties such as chain transfer function, excellent complexing function with metals, and photopolymerization function with double bonds. Features. Since thiol and polymerizable double bonds are highly reactive, thiol and polymerizable monomers cannot exist stably at the same time. Contents of the invention [0003] The object of the present invention is to provide a kind of styrenic monomer containing alkyl thiosulfate sodium (potassium) salt...

Claims

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Application Information

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IPC IPC(8): C07C381/00C08F28/02
Inventor 江金强宗奕吾代鹏刘晓亚林凤英张胜文陈明清倪忠斌
Owner JIANGNAN UNIV
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