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Acrylate type polychain transfer agent, its preparation method and its application in the preparation of columnar polymer brushes

A columnar polymer brush and acrylate-type technology, which is applied in the application field of preparing columnar polymer brushes, can solve the problems of complex structure, cumbersome synthesis process, and limited application of small molecule thioester compounds, and achieve simple and efficient introduction, huge Application prospects, the effect of reducing production costs

Active Publication Date: 2017-02-22
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Introduction of thioester fragments through esterification reaction, click reaction, substitution reaction, etc. 44,4372–4383), but the structure of the small molecule thioester compound used in it is complex, the synthesis process is cumbersome, and the cost is high, which limits its application in the field of columnar polymer brushes

Method used

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  • Acrylate type polychain transfer agent, its preparation method and its application in the preparation of columnar polymer brushes
  • Acrylate type polychain transfer agent, its preparation method and its application in the preparation of columnar polymer brushes
  • Acrylate type polychain transfer agent, its preparation method and its application in the preparation of columnar polymer brushes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] 3.0 g of methacrylate-2-(2-bromo-2-methylpropionyl)oxyethyl ester (BIEM), 11.7 mg of chain transfer agent dithiobenzoic acid-2-phenylpropan-2-ester ( CDB), 2.35mg AIBN, and 10mL anisole were added to the reaction flask, the molar ratio of BIEM, AIBN, and CDB was 250:0.33:1, reacted at 70°C for 24 hours, dissolved and precipitated in 200mL n-hexane for 3 times to remove small molecules Body, vacuum-dried to get light pink homopolymer main chain polymethacrylate-2-(2-bromo-2-methylpropionyl)oxyethyl ester (PBIEM), yield was 40%, polymerization main chain NMR calculation The degree of polymerization is 185, the SEC number average molecular weight is 19.4 kDa, and the molecular weight distribution is 1.27.

[0055] Add 0.25g of PBIEM, 0.515mL of stannous octoate, 354.5mg of benzothiodithioperoxyanhydride, 40μL of ethyl 2-bromoisobutyrate and 20mL of toluene into the reaction flask, and pass argon for 0.5h. Deoxygenated (127mg) cuprous bromide / (1.11mL) PMEDTA was added into...

Embodiment 2

[0058] Other polymerization conditions are the same as in Example 1, except that the PBIEM-g-PtBMA obtained in 1 is used to continue to synthesize block side chains. The monomer used is oligoethylene glycol methacrylate (OEGMA), and the specific steps are as follows: add 1.111g OEGMA, 20mg PBIEM-g-PtBMA, 0.2436mg AIBN and 10mL anisole into the reaction flask, and react at 60°C 27h, after the reaction was over, use 200mL of methanol to precipitate 3 times to remove the monomer to obtain polymethacrylate-2-(2-bromo-2-methylpropionyl)oxyethyl ester-g-(polymethacrylate tert-butyl -b-polyethylene glycol methacrylate) PBIEM-g-(PtBMA-b-POEGMA), the yield is 25%, the side chain polymerization degree calculated by NMR is 62.5, and the SEC number average molecular weight is 896.5 kDa, molecular weight distribution is 1.10.

Embodiment 3

[0060] Other polymerization conditions are the same as in Example 1, except that the polymerized monomer for the side chain is OEGMA, and the polymethacrylic acid-2-(2-bromo-2-methylpropionyl)oxyl group of the homopolymerized side chain is synthesized. Ethyl-g-polyethylene glycol methacrylate (PBIEM-g-POEGMA) was reacted at 60°C for 24h. After the reaction, the monomer was removed by precipitation with 150mL ether for 3 times. The yield was 37%. The degree of side chain polymerization calculated by NMR is 50, the SEC number average molecular weight is 434.2kDa, and the molecular weight distribution is 1.27.

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Abstract

The invention discloses an acrylate-type poly-chain transfer agent as well as a preparation method and an application of the poly-chain transfer agent in the preparation of a columnar polymer brush. The acrylate-type poly-chain transfer agent is prepared by synthesizing a main chain containing bromine (or chlorine) functional groups by virtue of RAFT and then introducing disulfide ester functional fragments by virtue of a one-step method. The columnar polymer brush is synthesized from the obtained acrylate-type poly-chain transfer agent by adopting a synthesis strategy of 'grafting from main chain' through the RAFT method, homopolymer and block copolymer containing multifunctional branched monomers can be obtained, namely, a brush-shaped homopolymer and a copolymer are obtained. The main chain of the polymer molecular brush is a (meth) acrylate polymer and the side chain of the polymer molecular brush is polystyrene, poly(meth)acrylate and poly(meth)acrylamide or a copolymer thereof. By the preparation method, the tedious steps used in the synthesis of a complex chain transfer reagent are avoided, the pollution caused by the tedious steps is decreased, the synthesized columnar polymer brush has a controllable structure and the preparation method provides a more simple and efficient method to synthesize the functional columnar polymer brush.

Description

technical field [0001] The invention belongs to the technical field of polymer material synthesis and preparation, and in particular relates to an acrylate polychain transfer agent, its preparation method and its application in the preparation of columnar polymer brushes. Background technique [0002] Cylindrical Polymer Brush (Cylindrical Polymer Brush) refers to a graft copolymer in which one end of a polymer molecular chain as a side chain is chemically bonded to a linear or dendritic macromolecule as a main chain at high density. Due to the existence of high-density long side chains, molecular brushes exhibit unique molecular morphology, bulk properties and solution behaviors different from linear macromolecules, thus making polymer brushes in nanopolymer materials (Macromolecules 2012,45,2619–2631; Macromolecules 2003,36,7894–7898), drug release (J.Am.Chem.Soc.2010,133,559–566), supramolecular chemistry (Macromolecules 1997,30,2002–2007) and other fields have potential ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F222/18C08F2/38C08F8/34C08F220/18C08F212/08C08F220/54C08F220/06C08F293/00
Inventor 凌君曹方义黄雁鑫
Owner ZHEJIANG UNIV
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