Antibacterial polymerizable monomer containing halide imidazolium salt structure and its preparation method and application

A technology of imidazolium halide and polymerized monomers, which is applied in the field of polymerizable monomers, can solve the problems of unsustainable antibacterial properties, drug resistance of bacteria, and decreased mechanical properties of bone cement, etc., and achieve the effect of broad-spectrum and high-efficiency antibacterial properties

Active Publication Date: 2020-05-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a series of antibacterial agents that can endow acrylate bone cement with long-acting antibacterial properties in view of the shortcomings of the existing antibiotic-containing bone cement that will cause the mechanical properties of the bone cement to decrease, the antibacterial property is not durable, and bacteria will develop drug resistance. Preparation method and application of permanent methacrylate monomer

Method used

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  • Antibacterial polymerizable monomer containing halide imidazolium salt structure and its preparation method and application
  • Antibacterial polymerizable monomer containing halide imidazolium salt structure and its preparation method and application
  • Antibacterial polymerizable monomer containing halide imidazolium salt structure and its preparation method and application

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Effect test

Embodiment 1

[0036] This embodiment prepares A 2 B 12 F monomer, the main steps are as follows:

[0037] Add 1.12g of N-hydroxyethylimidazole and 50mL of tetrahydrofuran into the reaction vessel, add 1.55g of isocyanoethyl methacrylate dropwise at a rate of 20 drops per minute under stirring, and react at 45°C for 12 hours , to completely react the isocyanate group, then adjust the reaction temperature to 65°C, add 2.49g bromododecane, react for 72 hours, and generate the product, and then perform purification treatment to obtain A 2 B 12 Type F monomer, the product is characterized by H NMR spectrum:

[0038] 1H-NMR (DMSO-d6, 600MHz): δ0.85[3H, t], 1.24[18H, s], 1.79[2H, m], 1.87[3H, s], 3.24[2H, q], 4.07[ 2H,t], 4.20[2H,t], 4.32[2H,t], 4.45[2H,t], 5.68[1H,s], 6.05[1H,s], 7.52[1H,t], 7.80[1H ,s], 7.85[1H,s], 9.29[1H,s]

Embodiment 2

[0040] This embodiment prepares A 2 B 16 F monomer, the main steps are as follows:

[0041]Add 1.12g of N-hydroxyethylimidazole and 50mL of tetrahydrofuran into the reaction vessel, add 1.55g of isocyanoethyl methacrylate dropwise at a rate of 20 drops per minute under stirring, and react at 45°C for 12 hours , to completely react the isocyanate group, then adjust the reaction temperature to 65°C, add 3.05g of hexadecane bromide, and react for 72 hours to generate the product, which is then purified to obtain A 2 B 16 Type F monomer, the product is characterized by H NMR spectrum:

[0042] 1H-NMR (DMSO-d6, 600MHz): δ0.85[3H, t], 1.23[26H, s], 1.77[2H, m], 1.87[3H, s], 3.24[2H, q], 4.07[ 2H,t], 4.19[2H,t], 4.32[2H,t], 4.44[2H,t], 5.68[1H,s], 6.04[1H,s], 7.49[1H,t], 7.79[1H ,s], 7.84[1H,s], 9.26[1H,s]

Embodiment 3

[0044] This embodiment prepares A 2 B 18 F monomer, the main steps are as follows:

[0045] Add 1.12g of N-hydroxyethylimidazole and 50mL of tetrahydrofuran into the reaction vessel, add 1.55g of isocyanoethyl methacrylate dropwise at a rate of 20 drops per minute under stirring, and react at 45°C for 12 hours , to completely react the isocyanate group, then adjust the reaction temperature to 65°C, add 3.33g bromododecane, react for 72 hours, and generate the product, and then perform purification treatment to obtain A 2 B 18 Type F monomer, the product is characterized by H NMR spectrum:

[0046] 1H-NMR (DMSO-d6, 600MHz): δ0.85[3H, t], 1.24[30H, s], 1.79[2H, m], 1.87[3H, s], 3.25[2H, q], 4.07[ 2H,t], 4.20[2H,t], 4.32[2H,t], 4.45[2H,t], 5.68[1H,s], 6.05[1H,s], 7.51[1H,t], 7.80[1H ,s], 7.85[1H,s], 9.30[1H,s]

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Abstract

The invention discloses an antibacterial polymeric monomer containing a halogenated imidazolium salt structure and a preparation method and application of the antibacterial polymeric monomer. The antibacterial polymeric monomer containing the halogenated imidazolium salt structure can be used as an antibacterial additive of acrylic bone cement. The monomer has the characteristics that the acrylic bone cement can be endowed with very high antibacterial property, the influence on curing time of the self-coagulating acrylic bone cement is small, the dough time of the bone cement can be significantly shortened, and meanwhile, the bone cement containing the monomer is good in mechanical property.

Description

technical field [0001] The invention relates to a series of polymerizable monomers that can be used as acrylate bone cement additives, in particular to an antibacterial polymerizable monomer containing a halogenated imidazolium salt structure and its preparation method and application. Background technique [0002] my country is currently moving towards an aging society, and the number of orthopedic degenerative diseases associated with the elderly population continues to increase. Moreover, the incidence of bone defects caused by industrial accidents, traffic accidents, and orthopedic diseases has remained at a high level for a long time. Therefore, it is necessary to use artificial materials for bone repair. [0003] Acrylate bone cement is the most widely used clinical bone repair material for orthopedic surgery. Its main component is polymethyl methacrylate (PMMA), which is biologically inert. Acrylate bone cement usually consists of two parts, powder and liquid, which...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/60C04B24/28A01P1/00
CPCC04B24/288C04B2103/67C07D233/60
Inventor 何经纬刘芳朱文彬
Owner SOUTH CHINA UNIV OF TECH
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