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A kind of azide polymer with polynorbornene main chain structure and preparation method thereof

A technology of polynorbornene and main chain structure, which is applied in the field of preparation of azide polymers, can solve the problems of harsh reaction conditions, single structure and low synthesis efficiency, and achieves mild preparation conditions, accurate material structure and narrow molecular weight distribution. Effect

Active Publication Date: 2020-11-13
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, there are two main problems in the synthesis of azide polymers: (1) the structure of azide polymers is single, all of which are azide polyethers, and the synthesis of monomers is generally long; (2) the synthesis method is two steps In the first method, cationic ring-opening polymerization is used to prepare azide polymer prepolymer, and then it is subjected to addition polymerization reaction with isocyanate
For cationic ring-opening polymerization, the reaction conditions are harsh, the relative molecular mass and distribution of the polymer are difficult to control, and the synthesis efficiency is not high; and the reaction involving isocyanate is usually very sensitive to moisture

Method used

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  • A kind of azide polymer with polynorbornene main chain structure and preparation method thereof
  • A kind of azide polymer with polynorbornene main chain structure and preparation method thereof
  • A kind of azide polymer with polynorbornene main chain structure and preparation method thereof

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preparation example Construction

[0046] The embodiment of the present invention provides a kind of preparation method of the azide polymer with polynorbornene main chain structure, refer to figure 1 , which shows a flow chart of a method for preparing an azide polymer having a polynorbornene main chain structure according to an embodiment of the present invention, the method comprising the following steps:

[0047] Step 101, carry out Diels-Alder reaction with maleic diol and cyclopentadiene as reaction raw materials, and obtain norbornene dimethanol having the following structural formula (I) after purification treatment.

[0048]The Diels-Alder reaction, also known as the Diels-Alder reaction, is a cycloaddition reaction. Conjugated dienes react with substituted alkenes (commonly known as dienophiles) to form substituted cyclohexenes.

[0049] In this step, maleic diol, as a dienophile, undergoes a cycloaddition reaction with cyclopentadiene to generate norbornene dimethanol, and a large amount of norborne...

Embodiment 1

[0081] Step (1), preparation of norbornene dimethanol.

[0082] The reaction equation is as follows:

[0083]

[0084] Take freshly prepared cyclopentadiene (10mL, 0.12mol) and maleic diol (5mL, 0.06mol) into a 50mL reaction flask with a stirrer, vacuumize, stir evenly, and place it at 200°C Under the oil bath, the stirring reaction was continued, and the reaction was about 8 hours. TLC detection showed that the reaction of maleic diol was complete, and the reaction was terminated. Ethyl acetate was added for washing, and the organic solvent was removed by rotary evaporation. After filtration, 8.5g of white solid matter was obtained, and the yield was 96.8%. %.

[0085] refer to figure 2 , shows the infrared spectrum of norbornene dimethanol in Example 1 of the present invention. refer to image 3 , shows the hydrogen nuclear magnetic resonance spectrum of norbornene dimethanol in Example 1 of the present invention. refer to Figure 4 , shows the carbon nuclear magne...

Embodiment 2

[0117] Take freshly prepared cyclopentadiene (10mL, 0.12mol) and maleic diol (10.7mL, 0.12mol) in a 50mL reaction flask with a stirrer, vacuumize it, stir it evenly, and place it at 10°C The lower oil bath continued to stir the reaction, and the reaction was about 64h. It was detected by TLC that the reaction of maleic diol was complete, the reaction was terminated, ethyl acetate was added to wash, the organic solvent was removed by rotary evaporation, and a white solid norbornene dimethanol was obtained by filtration, with a mass of 17.6 g and a yield of 95.3%.

[0118] Take norbornenediol (2g, 13mmol) and put it into a 250mL single-necked pear-shaped flask equipped with a magnetic stirrer, add DCM (20mL), place the single-necked pear-shaped flask on a magnetic stirrer, and stir to dissolve. After complete dissolution, MsCl (52 mmol, 4.0 mL) dissolved in tetrahydrofuran (20 mL) was added to a single-necked pear-shaped flask under ice-water bath conditions. Pyridine (52mmol, ...

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Abstract

The invention provides an azide polymer having a polynorbornene main chain structure, and a preparation method thereof. The preparation method comprises: 1, carrying out a Diels-Alder reaction on reaction raw materials such as cis-butenediol and cyclopentadiene, and carrying out purification treatment to obtain norbornene dimethanol; 2, dissolving the obtained norbornene dimethanol in an organic solvent, adding methylsulfonyl chloride and an alkali, carrying out a reaction for 1-7 h, and carrying out purification treatment to obtain norbornene dimethanesulfonate; 3, dissolving the obtained norbornene dimethanesulfonate in an organic solvent, adding a Grubbs catalyst, carrying out a ring-opening ectopic polymerization reaction for 4-72 h, adding a terminating agent to terminate the reaction, and filtering and drying to obtain polynorbornene dimethanesulfonate; and 4, dissolving the obtained polynorbornene dimethanesulfonate in a third organic solvent, adding an azide reagent, carrying out a reaction for 4-64 h at a temperature of 0-200 DEG C, adding water to terminate the reaction, filtering, and carrying out vacuum drying to achieve a constant weight so as to obtain the azide polymer.

Description

technical field [0001] The invention relates to the field of design chemistry and new materials, in particular to an azide polymer with a polynorbornene main chain structure and a preparation method for the azide polymer with a polynorbornene main chain structure. Background technique [0002] With the continuous pursuit of precision strike and high-efficiency damage capabilities of modern weapon systems such as rockets and missiles, people put forward higher and higher requirements for energetic materials as weapon energy carriers [J.Hazard.Mater.2008,151,289.]. Among them, energetic polymers used as binders [Energetic Polymers. National Defense Industry Press, 2011; Energetic Polymers: Binders and Plasticizers for Enhancing Performance. Wiley-VCH Verlag GmbH, 2012] are the matrix and skeleton of energetic materials, responsible for Provide carbon, hydrogen and other elements required for propellant and propellant combustion, and adjust the energy performance, mechanical pe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F132/04C08F8/30
CPCC08F8/30C08F132/04
Inventor 黄木华彭鸿鹏赵祖涛李婷婷罗运军
Owner BEIJING INSTITUTE OF TECHNOLOGYGY