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Initiating system of polymerization of acrylate monomer photoinduced electron transfer and reversible addition-fragmentation chain transfer

A technology of initiating system and chain transfer agent, which is applied in the field of new photosensitizer and initiating system, can solve the problems of self-quenching of porphyrin excited state, reducing the efficiency of photoredox catalyst, etc., and achieves the simple and easy preparation method and strong practicability Effect

Inactive Publication Date: 2019-02-26
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite the excellent photochemical properties of metalloporphyrins, aggregation of porphyrins in solution due to π-π stacking interactions would lead to severe self-quenching of porphyrin excited states, which would reduce its photooxidation as PET-RAFT polymerization Reduction Catalyst Efficiency

Method used

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  • Initiating system of polymerization of acrylate monomer photoinduced electron transfer and reversible addition-fragmentation chain transfer
  • Initiating system of polymerization of acrylate monomer photoinduced electron transfer and reversible addition-fragmentation chain transfer
  • Initiating system of polymerization of acrylate monomer photoinduced electron transfer and reversible addition-fragmentation chain transfer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1, the photopolymerization of MMA monomer under the zinc porphyrin-POSS / CDB initiation system (catalyst concentration 100 ppm)

[0027] The volume fraction of 2 mL monomeric MMA in dimethyl sulfoxide (DMSO) solvent (2 mL) was 50 %. According to the molar ratio [MMA]: [CDB]: [Zinc porphyrin-POSS] = 200: 1: 0.02, the above raw materials were respectively added into 12 mL single-branched glass bottles. Seal with a rubber stopper. Oxygen was removed by bubbling, nitrogen gas was passed in with a fine needle, and the other needle was used to vent gas. This continued for half an hour, so that the polymerization reaction was carried out under the irradiation of a 10 W green light strip in a nitrogen atmosphere. The specific reaction device is shown in Figure 1. At different time intervals, a small amount of samples were taken from the reaction system with a syringe, and the samples were used for nuclear magnetic testing to calculate the conversion rate. The sample w...

Embodiment 2

[0033] Example 2, the photopolymerization of MMA monomer under the zinc porphyrin-POSS / CDB initiation system (catalyst concentration 50 ppm)

[0034] Referring to Example 1, the photopolymerization of the MMA monomer under the zinc porphyrin-POSS / CDB initiation system was carried out. MMA monomer was 2 mL, and the molar ratio of [MMA]:[CDB]:[Zinc porphyrin-POSS] was 200:1:0.01. Samples taken at different time periods were precipitated with methanol three times, dried in vacuum to constant weight, and a light red substance was obtained. At 48 h, the monomer conversion rate was 51.02%, and the polymerization product M was measured by GPC n = 9800, PDI = 1.12. In addition, during the polymerization process, the molecular weight of the polymer increases linearly with the increase of the conversion rate, and the molecular weight distribution of the polymer is narrow (less than 1.3), which conforms to the law of living polymerization. After 48 h of light exposure time, the power...

Embodiment 3

[0037] Example 3, the photopolymerization of MMA monomer under the zinc porphyrin-POSS / CDB initiation system (catalyst concentration 25 ppm)

[0038] Referring to Example 1, the photopolymerization of the MMA monomer under the zinc porphyrin-POSS / CDB initiation system was carried out. Take 2 mL of monomeric MMA with a volume fraction of 50% monomer in dimethyl sulfoxide (DMSO) solvent (2 mL). Wherein the molar ratio of [MMA]:[CDB]:[zinc porphyrin-POSS] is 200:1:0.005. Samples taken at different time periods were precipitated with methanol three times, dried in vacuum to constant weight, and a light red substance was obtained. At 48 h, the monomer conversion rate was 34.25%, and the polymer product M was measured by GPC n = 7700, PDI = 1.15. In addition, during the polymerization process, the molecular weight of the polymer increases linearly with the increase of the conversion rate, and the molecular weight distribution of the polymer is narrow (less than 1.3), which confo...

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Abstract

The invention discloses a photosensitizer, a polymerization method and an initiating system for a polymerization technology of acrylate monomer photoinduced electron transfer and reversible addition-fragmentation chain transfer (PET-RAFT). The initiating system comprises the following components in parts by mole fraction: 20-400 parts of a monomer, 1-20 parts of a CDB chain transfer reagent, 0.001-0.1 part of a photosensitizer and 20-80% of a solvent, wherein the composition can undergo a photopolymerization chemical reaction under direct green light irradiation. The photosensitizer used in the the initialting system provided by the invention combines polyhedral oligomeric silsesquioxane (POSS) and metalloporphyrin through click chemistry for the first time, and the photosensitizer used has low toxicity and mild polymerization reaction conditions. Compared with a polymerization reaction catalyzed by tetraphenyl zinc porphyrin, the introduction of the POSS with a larger steric hindranceprevents aggregation of metalloporphyrins and greatly increases the polymerization reaction rate. The molecular weight of the homopolymer prepared by photopolymerization linearly increases with the increase of the conversion rate, and the molecular weight distribution of the polymer is narrow. The invention solves the problem of aggregation of porphyrin photosensitizers and widens the applicationfield of photopolymerization technology.

Description

technical field [0001] The present invention relates to an initiating system for active radical polymerization of visible light, in particular to a new type of polyhedral caged siloxane (POSS) containing azide group connected to metalloporphyrin by click chemistry at room temperature. A photosensitizer, a chain transfer agent, a polymerization system composed of acrylate monomers and solvents. Visible light-induced electron transfer reversible addition-fragmentation chain transfer (PET-RAFT) polymerization of acrylate monomers can be achieved using this initiator system. Background technique [0002] In recent years, light-controlled reversible-deactivation radical polymerization (RDRP) has attracted widespread attention due to its advantages of cheap and abundant light sources, polymerization at room temperature, easy operation, environmental friendliness, and convenient control of polymerization on and off. Boyer and co-workers utilized tris(2-phenylpyridine) iridium (fac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F120/14C08F2/38C08F2/50
CPCC08F120/14C08F2/38C08F2/50C08F2438/03
Inventor 汪贵城曹红亮刘峰张伟安吴健朱玉呈任正通施利凯王武龙赵影
Owner EAST CHINA UNIV OF SCI & TECH
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