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A kind of linear azobenzene polymer containing hydrogen bond and its preparation method and application

A linear azobenzene and polymer technology, applied in the field of polymer materials, can solve problems such as unfavorable large-scale industrial production, complex material synthesis, inability to reprocess, etc., and achieves low reaction environment and equipment requirements, simple synthesis steps, The effect of simplifying the reaction steps

Active Publication Date: 2022-07-12
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a result, most azobenzene polymers are difficult to process into three-dimensional structures, and are insoluble and infusible after molding, making it difficult to recycle and reuse
[0004] This problem can be improved to a certain extent by preparing a linear polymer first, and then crosslinking after melting or solution processing. For example, a photoresponsive block liquid crystal polymer with crosslinkable properties published in Chinese patent document CN101948562A and its preparation method, but the synthesis of this material is relatively complicated, and it cannot be processed again after processing once.
[0005] Synthesize a linear polymer with high molecular weight, and use the entanglement between its molecular chains to improve processability while maintaining deformability. For example, a side-chain linear azobenzene liquid crystal polymer published in Chinese patent document CN103087296A materials and their preparation methods, but this material has many synthesis steps, which is not conducive to large-scale industrial production

Method used

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  • A kind of linear azobenzene polymer containing hydrogen bond and its preparation method and application
  • A kind of linear azobenzene polymer containing hydrogen bond and its preparation method and application
  • A kind of linear azobenzene polymer containing hydrogen bond and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1: Synthesis of azobenzenediol AB1

[0073] Taking the 4,4'-dihydroxyazobenzene that is 5 parts by weight, the 6-bromo-1-hexanol that is 10 parts by weight, the potassium carbonate or potassium hydroxide that is 20 parts by weight, the weight parts are 0.1 part of potassium iodide, four raw materials were dissolved in 200 parts by weight of 2-butanone, N,N-dimethylformamide or N,N-dimethylacetamide, and the reaction was stirred at 80°C 12h, the solution was precipitated in water and recrystallized twice with absolute ethanol. The obtained solid was vacuum-dried at 40 °C for 12 h to obtain high-purity azobenzenediol AB1. The reaction equation for monomer AB1 is:

[0074]

[0075] The infrared spectrum and hydrogen nuclear magnetic resonance spectrum data of monomer AB1 are as follows:

[0076] FT-IR(KBr),v(cm -1 ): 3313(O–H), 2939, 2863(CH 2 ), 1601 (C=C), 1249 (Ar–O). 1 HNMR (600MHz, DMSO-d 6 )δ7.82(d,J=8.9Hz,4H),7.09(d,J=9.0Hz,4H),4.37(s,2H),4.05(t,J=...

Embodiment 2

[0077] Example 2: Synthesis of azobenzenediol AB2

[0078] Taking the 4,4'-dihydroxyazobenzene that the weight part is 5 parts, the 11-bromo-1-undecanol that the weight part is 15 parts, the potassium carbonate or the potassium hydroxide that the weight part is 20 parts, the weight part As 0.1 part of potassium iodide, the four raw materials were dissolved in 200 parts by weight of 2-butanone or N,N-dimethylacetamide, and the reaction was stirred at 80 °C for 12 hours, and the solution was precipitated in water. It was recrystallized twice from absolute ethanol. The obtained solid was vacuum-dried at 40 °C for 12 h to obtain high-purity azobenzenediol AB2. The reaction equation for monomer AB2 is:

[0079]

[0080] The infrared spectral data of monomer AB2 are as follows:

[0081] FT-IR(KBr),ν(cm -1 ): 3335 (O–H); 2918, 2850 (CH 2 ); 1602 (C=C); 1246 (Ar–O).

Embodiment 3

[0082] Example 3: Synthesis of azobenzenediol AB3

[0083] Take the 4,4'-dihydroxyazobenzene that is 5 parts by weight, the 2-chloroethoxyethanol of 15 parts by weight, the potassium carbonate or potassium hydroxide of 20 parts by weight, and the weight part is 0.1 parts of potassium iodide, the four raw materials were dissolved in 200 parts by weight of 2-butanone, N,N-dimethylformamide or N,N-dimethylacetamide, and the reaction was stirred at 80°C for 12h , the solution was precipitated in water and recrystallized twice with absolute ethanol. The obtained solid was vacuum-dried at 40 °C for 12 h to obtain high-purity azobenzenediol AB3. The reaction equation for monomer AB3 is:

[0084]

[0085] The H NMR data of monomer AB3 are as follows:

[0086] 1 H NMR (400MHz, DMSO-d 6 )δ7.83(d,J=8.9Hz,4H),7.12(d,J=9.0Hz,4H),4.66(s,2H),4.27–4.15(m,4H),3.84–3.73(m,4H ),3.52(q,J=2.9Hz,8H).

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Abstract

The invention belongs to the technical field of polymer materials, and relates to a linear azobenzene polymer containing hydrogen bonds and a preparation method and application thereof. The polymer molecular chain has a linear structure, the azophenyl element is located in the polymer main chain, and there is a hydrogen bond physical cross-linking provided by the urethane bond between the molecular chains. Compared with the prior art, the hydrogen bond-containing linear azobenzene polymer proposed by the present invention has simple synthesis steps, can be processed by melting and solution methods, and has unlimited molding size and shape, and can be recycled and reused after processing and molding. . Pre-edited or unedited after molding, polymers change shape when exposed to specific wavelengths of light. In addition, this polymer can greatly control its mechanical and light-responsive deformability by adjusting the spacers on both sides of the azobenzene and the structure of the diisocyanate.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, in particular to a linear azobenzene polymer containing hydrogen bonds and a preparation method and application thereof. Background technique [0002] Smart deformable material is a new type of functional material that can undergo specific shape changes under external stimuli, and has broad application prospects in smart fabrics, biomedicine, aerospace and other fields. By introducing photoresponsive groups or photothermal conversion particles, smart deformable materials can be controlled by light stimulation to achieve long-range, non-contact, high-resolution, instantaneous and wavelength-responsive deformation. [0003] At present, there are two main methods for constructing light-responsive smart deformable materials. One is to introduce photothermal conversion particles and use photothermal effect to realize remote control. Such materials are simple to process, but the introduction...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G18/32C08G18/75C08J5/18C09K19/38C08L75/04
CPCC08G18/3836C08G18/755C08J5/18C09K19/38C08J2375/04
Inventor 竺翀宇俞燕蕾孙家豪
Owner FUDAN UNIV
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