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Quaternary phosphonium salt-type antibacterial monomer and preparation method thereof

A quaternary phosphonium salt and monomer technology is applied in the field of quaternary phosphonium salt type antibacterial monomer and its preparation, and achieves the effect of stabilizing the molecular structure of the phosphonium salt

Inactive Publication Date: 2016-08-31
PEKING UNIV SCHOOL OF STOMATOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some studies have also found that some bacteria are resistant to nitrogen cationic organic antibacterial agents

Method used

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  • Quaternary phosphonium salt-type antibacterial monomer and preparation method thereof
  • Quaternary phosphonium salt-type antibacterial monomer and preparation method thereof
  • Quaternary phosphonium salt-type antibacterial monomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 Methacryloxy dodecyl bromide tributylphosphine (monomer 1)

[0037] 1) Add 22g of dodecabromohydrin into a 1000ml single-necked flask, add 250ml of dichloropropane and 16.5g of triethylamine, and add 14.76g of methacryloyl chloride dropwise under stirring. After the dropwise addition was complete, stirring was continued for 3 hours. After the reaction, the system was washed with water, saturated sodium carbonate and saturated brine respectively. The organic phase was dried over anhydrous sodium sulfate, concentrated and separated by chromatography. 19.5 g of dodecabromohydrin methacrylate was obtained with a yield of 73%.

[0038] 2) Add 7.6 g of dodecabromohydrin methacrylate into a 250 ml single-necked flask, add 100 ml of acetonitrile and 2.3 g of tributylphosphine, and stir for 5 hours under reflux. After the reaction, the system was concentrated and separated by chromatography. 3.631 g of salt was obtained with a yield of 59.2%.

[0039] 3) NMR spect...

Embodiment 2

[0041] Example 2 Methacryloyloxyoctyl bromide tributylphosphine (monomer 2)

[0042] 1) Add 20g of octabromohydrin into a 1000ml single-necked flask, add 250ml of dichloropropane and 17.7g of triethylamine, and add 16.65g of methacryloyl chloride dropwise while stirring. After the dropwise addition was complete, stirring was continued for 5 hours. After the reaction, the system was washed with water, saturated sodium carbonate and saturated brine respectively. The organic phase was dried over anhydrous sodium sulfate, concentrated and separated by chromatography. 18.4 g of octabromohydrin methacrylate was obtained, with a yield of 76%.

[0043] 2) Add 6.9 g of octabromohydrin methacrylate into a 250 ml one-necked flask, add 100 ml of acetonitrile and 2.4 g of tributylphosphine, and stir under reflux for 3 hours. After the reaction, the system was concentrated and separated by chromatography. 4.654 g of salt was obtained, with a yield of 62.7%.

Embodiment 3

[0044] Example 3 Methacryloxydecyl chloride tripropylphosphine (monomer 3)

[0045] 1) Add 23g of decachlorohydrin into a 1000ml one-necked flask, add 250ml of dichloropropane and 15.9g of triethylamine, and add 18.76g of methacryloyl chloride dropwise under stirring. After the dropwise addition was complete, stirring was continued for 4 hours. After the reaction, the system was washed with water, saturated sodium carbonate and saturated brine respectively. The organic phase was dried over anhydrous sodium sulfate, concentrated and separated by chromatography. 17.9 g of decachlorohydrin methacrylate was obtained with a yield of 68%.

[0046] 2) Add 6.5 g of decachlorohydrin methacrylate into a 250 ml one-necked flask, add 100 ml of acetonitrile and 2.1 g of tripropylphosphine, and stir under reflux for 3 hours. After the reaction, the system was concentrated and separated by chromatography. 3.724 g of salt was obtained with a yield of 60.1%.

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Abstract

The invention relates to a quaternary phosphonium salt-type antibacterial monomer shown in the formula and a preparation method thereof. One end of the monomer is an antibacterial group which is a quaternary phosphonium salt group, the other end of the monomer is a polymerizable group which is an acrylate group and the middle chain of the monomer is an alkyl chain segment. Through the polymerizable group, the monomer can be bonded to a dental restoration material through a chemical reaction so that the dental restoration material has long-term antibacterial properties. The invention also relates to a polymer prepared from the quaternary phosphonium salt-type antibacterial monomer as a polymerization monomer and also relates a dental restorative material containing the polymer.

Description

technical field [0001] The invention relates to a quaternary phosphonium salt type antibacterial monomer for dental restoration materials and a preparation method thereof. The invention also relates to a polymer material polymerized by using the quaternary phosphonium salt antibacterial monomer as a polymerization monomer, and a dental restoration material containing the polymer material. Background technique [0002] Polymer materials have been widely used in stomatology because of their good chemical properties, physical and mechanical properties, biocompatibility and ease of operation. Among them, composite resins, adhesives, and bases are widely used in caries prevention, restoration of dental dentition defects, and improvement of tooth color and appearance. However, the cured resin-based oral cavity material inevitably contains a small amount of unpolymerized monomers inside, and the volatilization or dissolution of residual monomers leads to rough surfaces and micropo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/54A61K6/083C08F30/02
CPCA61K6/887C07F9/5407C08F30/02C08L43/02
Inventor 徐永祥林红袁慎坡韩建民
Owner PEKING UNIV SCHOOL OF STOMATOLOGY