Poly(allyl ether) compound, and preparation method and application thereof

A technology of polyallyl ether and hydroxyl compounds, applied in the fields of polymer chemistry and materials science, can solve the problems of rare reports of alkyne and hydroxyl monomers, achieve excellent regioselectivity and stereoselectivity, and simple process , the effect of high polymerization efficiency

Active Publication Date: 2017-06-13
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the polymerization reaction of alkyne and hydroxyl monomers has rarely been reported in the fields of organic chemistry and polymers.

Method used

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  • Poly(allyl ether) compound, and preparation method and application thereof
  • Poly(allyl ether) compound, and preparation method and application thereof
  • Poly(allyl ether) compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050]The synthetic method of monomer M1 in the present embodiment can be according to published literature (Unoh Y, Hirano K, SatohT, et al.An Approach to Benzophosphole Oxides through Silver-or Manganese-Mediated Dehydrogenative Annulation Involving C-C and C-P BondFormation.Angewandte Chemie International Edition, 2013, 52: 12975-12979.) synthetic method preparation; the specific process is as follows: 1,4-diethynylbenzene (1.26g, 10mmol) and a stirrer bar were added in a 100mL two-necked flask, vacuum exchanged Nitrogen gas 4 times, 15 min each time; add 30 mL of dry tetrahydrofuran, stir at -78°C for 0.5 h; add 2.5 M n-butyllithium n-hexane solution (30 mmol, 12 mL) dropwise, and continue stirring for 1 h after addition; methyl iodide (40mmol, 2.4mL) was added dropwise to the reaction system at 0°C, and naturally returned to room temperature to react overnight; the reaction was quenched with saturated ammonium chloride solution, the organic phase was collected by extractio...

Embodiment 2

[0062] The synthesis method of monomer M1 in this example is the same as that in Example 1; M3 is trans-1,6-cyclohexyldimethanol, which can be purchased from the market, and in this example was purchased from TCI (Shanghai) Chemical Industry Development Co., Ltd.

[0063] A preparation method of polyallyl ether compound (P2), the steps are as follows:

[0064] (1) Add 92.4mg (0.6mmol) of monomer M1, 86.4mg (0.6mmol) of monomer M3, 69.4mg (0.06mmol) of tetrakistriphenylphosphine palladium and 13.4mg (0.12mmol) of benzoic acid into a 25mL polymerization tube ), vacuumize and change nitrogen for 3-5 times, inject 1.0mL of 1,4-dioxane with a syringe; place the polymerization tube in an oil bath at 100°C and stir for 24 hours (rotation speed: 400 rpm), After the reaction, the reaction solution was diluted to 30 mL with dichloromethane, extracted with 100 mL*3 of saturated saline, the organic phase was combined, and the organic phase was concentrated to 5 mL;

[0065] (2) Under the...

Embodiment 3

[0070] The synthesis method of monomer M1 in this example is the same as that in Example 1; M4 is 1,6-hexanediol, which can be purchased from the market, and in this example was purchased from TCI (Shanghai) Chemical Industry Development Co., Ltd.

[0071] A preparation method of polyallyl ether compound (P3), the steps are as follows:

[0072] (1) Add 92.4mg (0.6mmol) of monomer M1, 70.8mg (0.6mmol) of monomer M3, 69.4mg (0.06mmol) of tetrakistriphenylphosphine palladium and 13.4mg (0.12mmol) of benzoic acid into a 25mL polymerization tube ), evacuate and change nitrogen for 3 times, inject 1.0mL of 1,4-dioxane with a syringe; place the polymerization tube in an oil bath at 100°C and stir for 24 hours (rotation speed: 400 rpm), and the reaction ends Finally, dilute the reaction liquid with dichloromethane to 30 mL, extract with 100 mL of saturated brine, combine the organic phases, and concentrate the organic phases to 5 mL;

[0073] (2) Under the condition of stirring (the ...

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Abstract

The invention belongs to the fields of high polymer chemistry and material science, and discloses a poly(allyl ether) compound, and a preparation method and application thereof. The method comprises the following steps: (1) performing polymerization reaction on a binary propinyl compound and a binary hydroxyl compound in organic solvent in an inert gas protective atmosphere to obtain a crude product; and (2) performing post-treatment on the crude product to obtain the poly(allyl ether) compound. The poly(allyl ether) compound has a structure shown in Formula (I), wherein n is an integer of 2-200, and R2 is a same or different organic group. The method disclosed by the invention has the advantages of mild conditions, simple and accessible polymerizable monomers, high polymer yield, high molecular weight, high atom economy and excellent regioselectivity; and the poly(allyl ether) compound disclosed by the invention has excellent processability and high thermal stability. The Formula (I) is shown in the specification.

Description

technical field [0001] The invention belongs to the field of polymer chemistry and material science, and in particular relates to a polyallyl ether compound and its preparation method and application. Background technique [0002] Alkynes are one of the chemical raw materials that are easy to obtain or synthesize. The use of alkynes to construct functional polymers has important academic and technical significance, and has attracted widespread attention from scientists. The development of new polymerization methods based on alkyne monomers is of great importance for polymer materials science. At present, alkyne-based small molecule reactions have flourished and have been widely used in coatings, dyes, medicine and other fields. In the past few decades, scientists have done a lot of research on its reaction mechanism, catalytic system and application (Alonso F, Beletskaya I P, Yus M. Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes.Chemical Review...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/34
CPCC08G65/002C08G65/34
Inventor 唐本忠王佳秦安军赵祖金胡蓉蓉
Owner SOUTH CHINA UNIV OF TECH
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