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Quaternary ammonium lateral group-containing phenolphthalein type polyarylether, copolymer thereof and method for preparing same

A technology based on polyarylether and phenolphthalein, applied in the field of ion exchange membranes, can solve problems such as inability to eliminate batch differences, randomness in position and quantity, and impossibility of precise control, and achieve excellent solubility effects

Active Publication Date: 2010-06-16
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] This existing preparation technology is to introduce chloromethyl groups into the polymer main chain under catalytic conditions, which is easily affected by factors such as temperature, solvent, time, etc., and its position and number are random and cannot be precisely controlled. The difference between batches cannot be eliminated, which brings great difficulties to further functionalization reactions such as quaternization

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  • Quaternary ammonium lateral group-containing phenolphthalein type polyarylether, copolymer thereof and method for preparing same
  • Quaternary ammonium lateral group-containing phenolphthalein type polyarylether, copolymer thereof and method for preparing same
  • Quaternary ammonium lateral group-containing phenolphthalein type polyarylether, copolymer thereof and method for preparing same

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[0050] The present invention also provides a preparation method for the phenolphthalein type polyarylether containing quaternary ammonium side groups, comprising the following steps:

[0051] a) phenolphthalein bisphenol monomers containing tertiary amine side groups and dihalogen monomers are dissolved in an aprotic polar solvent and reacted to obtain polyarylethers containing tertiary amine side groups,

[0052] The phenolphthalein bisphenol monomer containing tertiary amine side group is HO-Ar3-OH, and Ar3 is That is, N-dimethylaminoethyl-3,3'-bis(4-hydroxyphenyl)benzopyrrole (PPH-DMEDA) or N-dimethylaminopropyl-3,3'-bis(4-hydroxyphenyl) base) benzopyrrole (PPH-DMPDA);

[0053] Dihalogen monomer is X-Ar1-X, X is halogen,

[0054] Ar1 is one of

[0055] In the reaction, the molar ratio of the phenolphthalein bisphenol monomer containing the tertiary amine side group to the dihalogen monomer is 1:1.

[0056] Reaction preferably uses catalyzer, and catalyzer is ...

Embodiment 1

[0078] Add 3.8846 grams of N-dimethylaminoethyl-3,3'-bis(4-hydroxyphenyl)benzopyrrolidone (PPH-DMEDA) in a three-necked flask equipped with mechanical stirring, condenser, and water separator (0.01mol), dichlorodiphenyl sulfone 2.8716 grams (0.01mol), potassium carbonate 2.1 grams (0.015mol), NMP (N-methylpyrrolidone) 35ml.

[0079] Stir at room temperature for 10 minutes under the protection of nitrogen, add 15 ml of toluene, raise the temperature to 150°C, evaporate the toluene after azeotropic removal of water for 4 hours, heat up to 180°C and polymerize for 10 hours to obtain a viscous solution, add DMF to dilute, filter out insoluble thing. Pour into water to precipitate a white solid, wash with water several times, and dry in vacuo. The intrinsic viscosity is 0.6dL / g.

[0080] Add 2 grams of the obtained white solid and 20 milliliters of NMP into a single-necked flask equipped with magnetic stirring and a condenser, and after fully stirring and dissolving, add 1 gram o...

Embodiment 2

[0084] Add 3.8846 grams of N-dimethylaminoethyl-3,3'-bis(4-hydroxyphenyl)benzopyrrolidone (PPH-DMEDA) in a three-necked flask equipped with mechanical stirring, condenser, and water separator (0.01mol), difluorodiphenyl sulfone 0.01mol, potassium carbonate 0.018mol, dimethyl sulfoxide 40ml.

[0085] Stir at room temperature for 10 minutes under the protection of nitrogen, add 15 ml of toluene, heat up to 140°C, evaporate the toluene after azeotropic water removal for 5 hours, heat up to 160°C and polymerize for 15 hours to obtain a viscous solution, add DMF to dilute, filter out insoluble thing. Pour into water to precipitate a white solid, wash with water several times, and dry in vacuo. The intrinsic viscosity is 0.9dL / g.

[0086] Add 2 grams of the obtained white solid and 20 milliliters of dimethyl sulfoxide into a single-necked flask equipped with magnetic stirring and a condenser, stir and dissolve, add 1 gram of methyl iodide, and react at 35 degrees for 9 hours. Aft...

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Abstract

The invention provides quaternary ammonium lateral groups-containing phenolphthalein type polyarylether and the method for preparing the same. The preparation method comprises the following steps of: dissolving a bisphenol monomer and a di-halogen monomer of tertiary amine lateral groups-containing phenolphthalein, which serve as raw materials, into an aprotic polar solvent to perform a reaction to obtain the tertiary amine lateral groups containing polyarylether; and after the reaction is ended, dissolving the obtained tertiary amine lateral groups-containing polyarylether in the aprotic polar solvent to perform a reaction with halogenated hydrocarbons. The preparation method can accurately control the positions and number of the quaternary ammonium functional groups, avoids the use of chloromethylation reagent(such as methylchloromethyl ether) which is highly poisonous and a strong carcinogen; and the obtained quaternary ammonium lateral groups containing phenolphthalein type polyarylether has good dissolvability and contributes to the further functionalized application; and the tertiary amine groups contained in the intermediate product of the tertiary amine lateral group-containing polyarylether easily make other similar reactions so as to derive other functional groups.

Description

technical field [0001] The invention relates to the technical field of ion exchange membranes, in particular to a quaternary ammonium side group-containing phenolphthalein type polyarylether and a preparation method thereof, a quaternary ammonium side group-containing phenolphthalein type polyarylether copolymer and a preparation method thereof. Background technique [0002] Quaternized polyarylethers have been widely used in nanofiltration membranes, ultrafiltration membranes, anion exchange resins, and conductive membranes for alkaline fuel cells. Existing preparation technology generally comprises three steps: polymerization, chloromethylation, quaternization, and reaction formula is as follows: [0003] [0004] This existing preparation technology is to introduce chloromethyl groups into the polymer main chain under catalytic conditions, which is easily affected by factors such as temperature, solvent, time, etc., and its position and number are random and cannot be ...

Claims

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Application Information

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IPC IPC(8): C08G65/48C08G65/40B01D71/52B01J41/12B01J41/13
Inventor 张所波张强
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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