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Asymmetric Free Radical Copolymerization of Methacrylate Chiral Polymers

A technology of methacrylic acid and polymers, which is applied in the field of synthesis of methacrylate chiral polymers, can solve the problems of less research on copolymerization systems, and achieve the effects of simple operation, wide sources and high yield

Active Publication Date: 2017-06-20
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The above researches explored the bulky methacrylate monomers and their polymerization process through the homopolymerization method, but there were relatively few studies on the copolymerization system of such bulky monomers and other functional monomers (J Am Chem Soc, 1995,117,5377; Proc Natl Acad Sci USA,2004,101,5461), and the research on the copolymerization behavior of chiral functional monomers and bulky methacrylates, and the composition and structure of such copolymers are important for their two The effects of order structure, stereoregularity and optical activity have not been reported so far.

Method used

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  • Asymmetric Free Radical Copolymerization of Methacrylate Chiral Polymers
  • Asymmetric Free Radical Copolymerization of Methacrylate Chiral Polymers
  • Asymmetric Free Radical Copolymerization of Methacrylate Chiral Polymers

Examples

Experimental program
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Effect test

specific Embodiment approach 1

[0028] 1. Take 10.0g trityl chloride and fully dissolve it in toluene at room temperature, then N 2 Under protection, add methacrylic acid (equivalent to the equivalent of trityl chloride, such as figure 1 Shown), then add triethylamine dropwise (the dropping rate should be controlled to be 3 drops / second, 2.3 times the equivalent of trityl chloride), raise the temperature to 80°C, stir and reflux for 3.5h, stop the reaction and cool down, and wash with toluene And filtered, rotary steamed, purified by recrystallization method, and finally obtained pure trityl methacrylate monomer with a yield of 58%.

[0029] 2. Add 0.1g trityl methacrylate monomer into the polymerization tube, N 2 Add toluene under protection, stir until fully dissolved, and seal it for later use. Get a 25mL two-necked flask to configure azobisisobutyronitrile (AIBN) initiator solution, N2 Under protection, 0.08 g of azobisisobutyronitrile (AIBN) and 5 mL of toluene were sequentially added, and stirred un...

specific Embodiment approach 2

[0034] 1. Take 10.0g trityl chloride and fully dissolve it in toluene at room temperature, then N 2 Under protection, add methacrylic acid (equivalent to the equivalent of trityl chloride, such as figure 1 Shown), then add triethylamine dropwise (the dropping rate should be controlled to be 2 drops / second, 2.0 times the equivalent of trityl chloride), heat up to 80°C, stir and reflux for 4h, stop the reaction and cool down, wash with toluene and Filtration, rotary evaporation, and purification by recrystallization, finally obtained pure trityl methacrylate monomer with a yield of 61%.

[0035] 2. Add 0.1g trityl methacrylate monomer into the polymerization tube, N 2 Add toluene under protection, stir until fully dissolved, and seal it for later use. Get a 25mL two-necked flask to configure azobisisobutyronitrile (AIBN) initiator solution, N 2 Under protection, 0.08 g of azobisisobutyronitrile (AIBN) and 5 mL of toluene were sequentially added, and stirred until fully disso...

specific Embodiment approach 3

[0040] 1. Take 10.0g trityl chloride and fully dissolve it in toluene at room temperature, then N 2 Under protection, add methacrylic acid (equivalent to the equivalent of trityl chloride, such as figure 1 Shown), then add triethylamine dropwise (the dropping rate should be controlled to be 1 drop / second, 2.0 times the equivalent of trityl chloride), heat up to 80°C, stir and reflux for 4h, stop the reaction and cool down, wash with toluene and Filtration, rotary evaporation, and purification by recrystallization, finally obtained pure trityl methacrylate monomer with a yield of 64%.

[0041] 2. Add 0.1g trityl methacrylate monomer into the polymerization tube, N 2 Add toluene under protection, stir until fully dissolved, and seal it for later use. Get a 25mL two-necked flask to configure azobisisobutyronitrile (AIBN) initiator solution, N 2 Under protection, 0.08 g of azobisisobutyronitrile (AIBN) and 5 mL of toluene were sequentially added, and stirred until fully dissol...

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Abstract

The present invention provides a method for asymmetrical free-radicals of methacrylate chiral polymer. The method comprises: firstly performing a reaction on methacrylic acid with trityl chloride to generate a methacrylic acid / trityl chloride monomer in a large volume; then performing asymmetrical free-radical copolymerization on the monomer and a chiral functional monomer under specific free-radical polymerization conditions; and obtaining a methacrylate chiral copolymer in a large volume; and performing purification on the obtained polymer to finally obtain a target product. NMR (1H-NMR) and elemental analytical techonlogies are are used for structural characterization and analysis of the obtained polymer to determine that the molecular structure and the component ratio meet design requirements. Gel permeation chromatography and a polarimeter are used for performing in-depth analysis on performances of the synthesized copolymer to obtain molecular weight and distribution of the new chiral copolymer and features of optical activity. The synthesis route is clear and feasible, the process is sophisticated, the operations are simple, and the method is easy to implement; and the method can be used for large-scale batch production.

Description

technical field [0001] The invention relates to a method for synthesizing a methacrylate chiral polymer, in particular to an asymmetric radical copolymerization method for a methacrylate chiral polymer. Background technique [0002] Due to the great potential in the fields of formation mechanism, stereoregularity, and asymmetric functionalization, the asymmetric synthesis of optically active polymers has become a research hotspot that polymer scientists have paid much attention to in recent years. Some unique bulky monomers, such as trityl methacrylate (TrMA) and its homologues, can not only form highly isotactic polymers through the initiation of butyllithium in anionic polymerization systems, but also can be synthesized by All kinds of chiral anionic initiators directly form optically active polymers in asymmetric synthesis systems. The chirality of the formed polytrityl methacrylate mainly comes from its stable one-handed helical conformation, and the helical conformatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F222/14C08F226/06C08F4/04
Inventor 沈军李庚
Owner HARBIN ENG UNIV
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