Active free radical polymerization method with zinc phthalocyanine dye as near-infrared light catalyst

A polymerization method and near-infrared light technology, applied in the field of living radical polymerization, can solve the problems of not utilizing the photoconversion performance of phthalocyanine compounds, and the reaction products do not have "activity"

Active Publication Date: 2020-11-03
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] CN201210451694.1 and CN201310138388.7 respectively disclose a preparation method of a photoresponsive hyperbranched zinc phthalocyanine polymer and a polymer containing zinc phthalocyanine groups in the side chain and a preparation method thereof. Cyanine compounds are introduced into the main chain of polymers, but they are all to improve the solubility and processability of phthalocyanine polymers, improve the photoelectric properties of materials, and do not utilize the photoconversion properties of phthalocyanine compounds, and the reaction products are not "active"

Method used

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  • Active free radical polymerization method with zinc phthalocyanine dye as near-infrared light catalyst
  • Active free radical polymerization method with zinc phthalocyanine dye as near-infrared light catalyst
  • Active free radical polymerization method with zinc phthalocyanine dye as near-infrared light catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Example 1 Synthesis of polymeric zinc phthalocyanine dye near-infrared photocatalyst ZnTAPc-MAm

[0079] Dissolve zinc tetraaminophthalocyanine dye (ZnTAPc) (0.32g, 0.50mmol) in 20mL of DMF, add TEA (83.4μL, 0.60mmol), stir on a magnetic stirrer, and then dropwise add methacryloyl chloride (44.8 μL, 0.55mmol) mixed with anhydrous dichloromethane (10mL), stirred overnight at room temperature. Then the reaction solution was poured into 150 mL of water, and the solid product was separated and collected by suction filtration, and further purified by washing with 1.0 M hydrochloric acid and 1.0 M sodium hydroxide, respectively. Finally, the product was washed with deionized water and precipitated using 10000r min -1 Centrifuge at a high speed. The obtained dark blue-black product was used after being dried in a vacuum oven. The reaction scheme is as follows:

[0080]

Embodiment 2

[0081] Example 2 Synthesis of polymeric zinc phthalocyanine dye near-infrared photocatalyst ZnTAPc-Am

[0082] Disperse ZnTAPc (0.32g, 0.50mmol) in 20mL of DMF, add TEA (83.4μL, 0.60mmol), stir on a magnetic stirrer, then add dropwise acryloyl chloride (53.2μL, 0.55mmol) and anhydrous dichloro Methane (10 mL) mixed solution was stirred at room temperature overnight. Then the reaction solution was poured into 150 mL of water, and the solid product was separated and collected by suction filtration, and further purified by washing with 1.0 M hydrochloric acid and 1.0 M sodium hydroxide, respectively. Finally, the product was washed with deionized water and precipitated using 10000r min -1 Centrifuge at a high speed. The dark blue-black product obtained is the acrylamide zinc phthalocyanine dye monomer (ZnTAPc-Am) and dried in a vacuum oven with a product yield of 80.2%. The reaction scheme is as follows:

[0083]

Embodiment 3

[0084] Example 3 Synthesis of polymeric zinc phthalocyanine dye near-infrared photocatalyst ZnTAPc-A

[0085] (1) Synthesis of acid chloride compound (acrylic acid-3-chloro-3-oxopropyl ester): acid chloride 3-(acryloxy)propionic acid (79.30mg, 0.55 mmol) with thionyl chloride (5.0mL) , dropwise added two drops of DMF as a catalyst, stirred for 30 minutes, removed excess thionyl chloride by rotary evaporation, sealed and kept for the next step of reaction. The reaction scheme is as follows:

[0086]

[0087] (2) Synthesis of ZnTAPc-A: Dissolve ZnTAPc (0.32g, 0.50mmol) in 20mL of DMF, add TEA (83.4μL, 0.60mmol), stir on a magnetic stirrer, and then dropwise add acrylic acid-3-chloro- A mixed solution of 3-oxopropyl ester (89.40 mg, 0.55 mmol) and anhydrous dichloromethane (10.0 mL) was stirred overnight at room temperature. Then the reaction solution was poured into 150 mL of water, and the solid product was collected by suction filtration, and further washed and purified w...

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Abstract

The invention relates to an active free radical polymerization method with zinc phthalocyanine dye as near-infrared light catalyst, which comprises the following steps: in an air atmosphere, carryingout near-infrared light-controlled polymerization reaction on a free radical polymerization monomer in a solvent at 0-30 DEG C under the catalytic action of a chain transfer agent, a cocatalyst and zinc phthalocyanine dye containing carbon-carbon double bonds, thus obtaining an active free radical polymerization product after the reaction is completed, wherein the free radical polymerization monomer is selected from an acrylate monomer, a methacrylate monomer, an acrylamide monomer or a methacrylamide monomer, the chain transfer agent comprises thiocarbonate, and the cocatalyst comprises organic amine containing carbon-carbon double bonds or organic amine without carbon-carbon double bonds. According to the invention, the functional zinc phthalocyanine dye with near-infrared light responseis used as the near-infrared light catalyst for polymerization reaction; after polymerization is completed, the polymerizable zinc phthalocyanine dye is retained on a polymer chain in a polymerization manner, so that cyclic utilization of the near-infrared light catalyst is realized.

Description

technical field [0001] The invention relates to the technical field of polymer preparation, in particular to an active radical polymerization method using a zinc phthalocyanine dye as a near-infrared photocatalyst. Background technique [0002] Nowadays, a variety of reversible-inactivation free radical polymerization methods based on the reversible balance between active species and dormant species have been widely reported, and photocatalytic polymerization systems have also been used to synthesize Polymer materials with multiple functions, however, photocatalytic polymerization systems are generally limited by photocatalysts, because there are few types of catalysts that can be used in polymerization systems, and the synthesis, storage and use conditions of catalysts are also problems that need to be solved urgently. In addition, the existence of oxygen will have an important impact on some chemical synthesis work, such as providing a rich source of oxidant, but it has al...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F220/14C08F220/30C08F220/54C08F283/06C08F220/34C08F230/04C08F2/38C08F2/48
CPCC08F220/14C08F220/306C08F220/54C08F283/065C08F2/38C08F2/48C08F2438/03C08F220/34C08F230/04C08F2/50C08F220/286C08F2/46C08F4/50
Inventor 程振平田春张丽芬朱秀林
Owner SUZHOU UNIV
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