Cross-linked polyquaternary ammonium salt type antibiosis monomer, preparation method of cross-linked polyquaternary ammonium salt type antibiosis monomer and application of cross-linked polyquaternary ammonium salt type antibiosis monomer in dentistry repairing materials

A cross-linking polymerization, quaternary ammonium salt technology, applied in the preparation of organic compounds, the preparation of aminohydroxy compounds, dentistry, etc., can solve the problems of no bonding cross-linking system, decreased mechanical properties of materials, and inappropriate use of light-colored materials. , to reduce the probability that the double bond does not participate in the polymerization reaction, improve the safety of use, and achieve the effects of simple reaction steps

Inactive Publication Date: 2011-06-01
NANJING UNIV OF SCI & TECH
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

[0005] (1) Add organic antibacterial agents directly. This type of antibacterial agent has the advantages of fast onset of action, high antibacterial efficacy, and easy dispersion and mixing, but there are generally two disadvantages: first, its release kinetics show that within the first few days , the antibacterial agent is released in a large amount in the form of "burst release effect", and it is difficult to achieve long-term release of antibacterial ingredients; secondly, the mechanical properties of the material are significantly reduced after adding the antibacterial agent
[0006] (2) Wrap inorganic antibacterial agents. Inorganic antibacterial materials have the advantages of broad antibacterial spectrum, low toxicity, no drug resistance, and good chemical stability. However, silver is easy to vulcanize or oxidize, has poor light stability, and is easy to change color, so it is not suitable for shallow water. color materials, and the cost is higher
Therefore, there may be a small amount of antibacterial monomers that do not participate in the copolymerization reaction and are not bonded into the crosslinking system
Dental restoration materials will be used in the oral cavity for a long time, and the dissolution of unreacted monomers caused by long-term immersion will bring potential safety hazards to actual clinical applications.

Method used

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  • Cross-linked polyquaternary ammonium salt type antibiosis monomer, preparation method of cross-linked polyquaternary ammonium salt type antibiosis monomer and application of cross-linked polyquaternary ammonium salt type antibiosis monomer in dentistry repairing materials
  • Cross-linked polyquaternary ammonium salt type antibiosis monomer, preparation method of cross-linked polyquaternary ammonium salt type antibiosis monomer and application of cross-linked polyquaternary ammonium salt type antibiosis monomer in dentistry repairing materials
  • Cross-linked polyquaternary ammonium salt type antibiosis monomer, preparation method of cross-linked polyquaternary ammonium salt type antibiosis monomer and application of cross-linked polyquaternary ammonium salt type antibiosis monomer in dentistry repairing materials

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preparation example Construction

[0043] The steps of the preparation method of the crosslinkable polymerized quaternary ammonium salt type antibacterial monomer of the present invention are as follows:

[0044] In the first step, in the tertiary amine substance with OH group, any one of acetone, dichloromethane or acetonitrile is added as a solvent, and the halogenated hydrocarbon substance is added for reflux reaction to obtain product A, which is The quaternary ammonium salt of the hydroxyl group is added with a molar ratio of tertiary amine:halogenated hydrocarbon=1:1, and the reaction time is 6-36h. The tertiary amine has two or three OH groups, which are N-methyldiethanolamine, N-ethyl Diethanolamine or triethanolamine, halogenated hydrocarbons are 1-bromododecane, 1-bromohexadecane or benzyl chloride;

[0045] In the second step, the product A prepared in the first step reacts with any one of toluene, benzene, methylene chloride or tetrahydrofuran as a solvent, and adds an unsaturated acid chloride cont...

Embodiment 1

[0053] In the first step, add 0.1mol N-methyldiethanolamine to 100mL of acetonitrile, then add 1-bromohexadecane for reflux reaction, the molar ratio of the two is 1:1, and the reaction time is 20h. Dry to obtain white powdery product A;

[0054] In the second step, add 100 mL of dichloromethane to 0.05 mol of the above product A as a solvent, then add methacryloyl chloride to reflux reaction, the molar ratio of feed is A:acyl chloride=1:2.2, and react for 6 hours. Crystallization, vacuum drying and other methods to obtain the product 2-(methacryloyloxyethyl)-n-hexadecyl-methyl ammonium bromide;

[0055] In the third step, 2-(methacryloyloxyethyl)-n-hexadecyl-methylammonium bromide is mixed in the order of 0%, 1%, 2%, 3%, 4%, 5%, 6%, Add 7%, 8%, 9%, 10%, 15% (w / w) into a certain amount of Bis-GMA / HEMA, with N,N-dimethylaminoethyl methacrylate (DMAEMA) as the auxiliary initiator agent, camphorquinone (CQ) as a photoinitiator, ultraviolet light irradiation polymerization to pr...

Embodiment 2

[0063] In the first step, 0.1 mol of N-ethyldiethanolamine was added to 100 mL of acetone, and then 1-bromododecane was added for reflux reaction. The molar ratio of the two was 1:1, and the reaction time was 36 hours. After the reaction, the white powdery product A was obtained by suction filtration and drying;

[0064] In the second step, 100 mL of benzenedichloromethane was added to 0.05 mol of the above-mentioned product A as a solvent, and then acryloyl chloride was added for reflux reaction, and the molar ratio of feeding was A:acyl chloride=1:2.2, and the reaction was carried out for 6 hours. After the reaction, the product 2-(acryloyloxyethyl)-n-dodecyl-ethylammonium bromide was obtained by rotary evaporation, recrystallization, vacuum drying and other methods;

[0065] In the third step, 2-(acryloyloxyethyl)-n-dodecyl-ethylammonium bromide is added at 0%, 1%, 2%, 3%, 4%, 5%, 6%, 7%. , 8%, 9%, 10%, 15% (w / w) added in a certain amount of Bis-GMA / HEMA, with DMAEMA as a ...

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Abstract

The invention discloses a cross-linked polyquaternary ammonium salt type antibiosis monomer, a preparation method of the cross-linked polyquaternary ammonium salt type antibiosis monomer and application of the cross-linked polyquaternary ammonium salt type antibiosis monomer in dentistry repairing materials. In the preparation method, monomer bonds are connected to a dentistry resin-based material, so as to endow antibiosis property to the resin-based material. The structure general formula of the cross-linked polyquaternary ammonium salt type antibiosis monomer is shown in the specification. The preparation method comprises the following steps: 1, adding a solvent in tertiary amine substance, and adding halohydrocarbon substance for reflux reaction so as to obtain a product A, adding acyl chloride for reflux reaction by using toluene, benzene, dichloromethane or tetrahydrofuran so as to obtain quaternary ammonium salt B, and purifying the quaternary ammonium salt B; and 2, adding the acyl chloride and tertiary amine substancem by using the toluene, benzene, dichloromethane or tetrahydrofuran as the solvent, adding triethylamine as auxiliary, reacting to obtain the tertiary amine containing C=C, the tertiary amine takes acetone, metjylene dichloride and acetonitrile as the solvents, adding the halohydrocarbon for reflux reaction, and then purifying the quaternary ammonium salt monomer. In the invention, reaction steps are simple, the purity of the monomer is high, and the monomer has better compatibility and higher safety as compared with the common dentistry repairing resin monomer.

Description

technical field [0001] The invention belongs to the field of combination of macromolecular materials and biomedicine, in particular to a new type of cross-linkable polymeric quaternary ammonium salt type antibacterial monomer and its application in dental resin-based restoration materials. Background technique [0002] Quaternary ammonium antibacterial agents are a class of organic antibacterial agents that have been studied more. Compared with other antibacterial agents, quaternary ammonium salts have broad-spectrum antibacterial properties, low toxicity, stable performance, low corrosion, and long-term biological effects. is widely used. However, there are few reports on the application of quaternary ammonium salts in the study of oral biomaterials. [0003] Caries is a disease in which the hard tissue of the tooth body is chronically and progressively destroyed under the influence of various factors mainly including bacteria. The threat of harmful microorganisms in the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C219/08C07C213/06A61K6/027A61P31/04
Inventor 邢晓东祁玲玲李丽霞
Owner NANJING UNIV OF SCI & TECH
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