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Antibacterial methacrylate monomer containing thiazole ring structure and its preparation method and application

A technology of methacrylate and methacrylic acid, used in dental preparations, dental prostheses, compression mold cups, etc., can solve the problem of lack of antibacterial properties of dental restoration materials, and achieve the effect of broad-spectrum and high-efficiency antibacterial properties

Active Publication Date: 2016-01-06
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide antibacterial methacrylate monomers containing a thiazole ring structure and its preparation method and application for the lack of antibacterial properties of methacrylate dental restoration materials

Method used

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  • Antibacterial methacrylate monomer containing thiazole ring structure and its preparation method and application
  • Antibacterial methacrylate monomer containing thiazole ring structure and its preparation method and application
  • Antibacterial methacrylate monomer containing thiazole ring structure and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) The preparation method of monomer is as follows:

[0028] Add 11.5g 5-hydroxymethylthiazole in the 150ml there-necked flask that magnetic stirring bar is housed, constantly add 15.5g methacrylic acid (2-isocyanatoethyl) ester through constant pressure dropping funnel under stirring state, use 30ml of acetone rinsed the constant pressure dropping funnel, reacted at 45°C for 12 hours, and then purified the reaction product, with a yield of 95%. FT-IR: ν (cm-1) 3345, 3080, 2956, 2929, 2894, 1715, 1636, 1525, 1453, 1403, 1254, 1167, 777, 652, 602; 1H-NMR (400MHz, CDCl 3 ): δ8.81(s, 1H), 7.87(s, 1H), 6.10(s, 1H), 5.59(s, 1H), 5.31(s, 2H), 5.20(s, 1H), 4.22-4.25( m, 2H), 3.50-3.54 (m, 2H), 1.93 (s, 3H).

Embodiment 2

[0030] (II) The preparation method of monomer is as follows:

[0031] Add 14.3g of 4-methyl-5thiazole ethanol in a 150ml three-necked flask equipped with a magnetic stirring bar, and continuously add 16.28g of methacrylic acid (2-isocyanatoethyl) ester through a constant pressure dropping funnel under stirring , rinse the constant-pressure dropping funnel with 30ml of acetone, react at 20°C for 24 hours, and then purify the reaction product, with a yield of 98%. FT-IR: ν (cm-1) 3362, 3068, 2955, 2929, 2894, 1716, 1635, 1539, 1451, 1414, 1257, 1164, 777, 656; 1H-NMR (400MHz, CDCl 3 ): δ8.60(s, 1H), 6.12(s, 1H), 5.60(s, 1H), 5.07(s, 1H), 4.22-4.26(m, 4H), 3.48-3.52(m, 2H), 3.03-3.11 (m, 2H), 2.41 (s, 3H), 1.95 (s, 3H).

Embodiment 3

[0033] Antibacterial Properties of Dental Resin Containing (I) Monomer

[0034] In this example, the (I) monomer was mixed with the resin system UDMA / TEGDMA system commonly used in dental restorative materials, and the antibacterial properties of the prepared resin after curing were studied. The resin formulation and antibacterial properties are shown in Table 1.

[0035] It can be seen from Table 1 that adding the synthesized (I) monomer to the resin system for dental restoration materials can endow it with effective antibacterial properties.

[0036] Table 1 contains (I) resin composition and cured product antibacterial property

[0037]

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Abstract

The invention discloses an antibacterial metacrylic acid ester monomer with a thiazole ring structure as well as a preparation method and application thereof. The preparation method of the antibacterial metacrylic acid ester monomer with the thiazole ring structure comprises the following steps: adding 5-hydroxymethyl thiazole or 4-methyl-5 thiazole ethanol into a three-opening flask with a magnetic stirrer, adding methyl crylic acid (2-isocyano ethyl) ester or methacrylic acid (2-isocyano ethyl) ester in a stirring state, subsequently adding a certain amount of acetone to reduce the viscosity of the system, reacting the mixture at 10-70 DEG C for 12-36 hours, and subsequently performing purification treatment on a reaction product. The monomer has broad spectrum efficient antibacterial properties and can be both applied to dental repairing materials together with other monomers and independently applied to a main body resin.

Description

technical field [0001] The invention relates to a series of monomers that can be used as a photoinitiated polymerization system, in particular to an antibacterial methacrylate monomer containing a thiazole ring structure and its preparation method and application. Background technique [0002] Dental caries is a common and frequently-occurring disease in clinical oral cavity, and is listed as one of the three major human diseases by the World Health Organization. If the carious site is not repaired in time, the lesion will develop to the deep layer, leading to pulp inflammation, periapical infection and other complications, causing tissue damage and severe pain, and even affecting the health of the whole body. Therefore, it is necessary to carry out effective restorative treatment for dental caries. [0003] Methacrylate polymers are widely used as dental restoration materials due to their excellent biocompatibility and adhesive properties. Bis-GMA, a methacrylate monomer ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/24C08F220/36A61K6/083
CPCA61K6/887C07D277/24C08F20/38
Inventor 何经纬罗韦逊刘芳
Owner SOUTH CHINA UNIV OF TECH
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