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Preparation method of quaternary degradable antibacterial agent

A kind of antibacterial agent, quaternization technology, applied in the field of preparation of degradable polyester antibacterial agent, can solve the problems such as difficult to remove, poor biocompatibility, etc., achieve good antibacterial performance, good stability and biocompatibility, and prepare The effect of simple process

Inactive Publication Date: 2011-06-15
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these antibacterial agents have poor biocompatibility and are not easy to remove from the environment after exerting their antibacterial properties.

Method used

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  • Preparation method of quaternary degradable antibacterial agent
  • Preparation method of quaternary degradable antibacterial agent
  • Preparation method of quaternary degradable antibacterial agent

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0019] 1) Synthesis of 2,2-dibromomethyltrimethylene carbonate monomer (DBTC)

[0020] 7.0 g (0.03 mol) of dibromoneopentyl glycol and 5.7 mL (0.06 mol) of ethyl chloroformate were added to a round bottom flask containing 200 mL of THF at a ratio of 1:2, and the mixture was stirred at 0 °C for 30 min. And drop 8.3mL (0.06 mol) of triethylamine (TEA) into the round-bottomed flask, stir overnight at room temperature, filter off the TEA·HCl precipitate, concentrate the filtrate under reduced pressure and then precipitate with ether to obtain 2, 2-Dibromomethyltrimethylene carbonate monomer, its H NMR spectrum is shown in Figure 1.

[0021] 2) Polymerization of DBTC and caprolactone (poly(DBTC- co -CL)).

[0022] In the polymerization bottle, add 2,2-dibromomethyltrimethylene carbonate monomer and caprolactone in different feeding ratios, and press 2,2-dibromomethyltrimethylene carbonate monomer under the protection of argon The molar ratio of the sum of the moles of caprolact...

example 2

[0031] 1) Monomer is synthesized with example 1

[0032]2) Synthesis of 2,2-dibromomethyltrimethylene carbonate (DBTC) homopolymer (PDBTC)

[0033] Add 0.2 g (0.69 mmol) 2,2-dibromomethyltrimethylene carbonate monomer to the polymerization bottle, and add 0.7 mg catalyst Sn( Oct) 2 , sealed under argon protection, and polymerized at 110 °C for 12 h. The product was eluted with a little THF and precipitated with ether.

[0034] 3) Synthesis of quaternized degradable antimicrobial agent based on PDBTC

[0035] PDBTC ​​was added into a 100 mL round-bottomed flask according to the molar ratio of Br functional group to alkyl tertiary amine 1:2, and then KBr with twice the molar number of bromine functional groups was added as a catalyst, and DMF was used as a solvent to react at 80 °C for 120 h, namely Get the product.

example 3

[0037] 1) Monomer is synthesized with example 1

[0038] 2) 2,2-Dibromomethyltrimethylene carbonate (DBTC) and monomethoxypolyethylene with a molecular weight of 1000

[0039] Diol (mPEG 1000 -OH) copolymerization (mPEG 1000 -co-PDBTC).

[0040] In the polymerization bottle, add 2,2-dibromomethyltrimethylene carbonate monomer and mPEG in a mass ratio of 1:1 1000 -OH, by 2,2-dibromomethyltrimethylene carbonate monomer and mPEG under argon 1000 The molar ratio of the molar sum of -OH to the catalyst is 400:1 and the catalyst Sn(Oct) is added 2 , sealed under the protection of argon, and polymerized at 110 ℃ for 12 h. The product was eluted with THF and precipitated with ether.

[0041] 3) with mPEG 1000 Synthesis of quaternized degradable antibacterial agent with -co-PDBTC ​​as the backbone

[0042] mPEG 1000 -co-PDBTC ​​was added to a 100 mL round-bottomed flask at a molar ratio of Br functional group to alkyl tertiary amine of 1:2, and then KBr with twice the molar nu...

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Abstract

The invention discloses a preparation method of a quaternary degradable antibacterial agent, and the preparation method comprises the following steps: homopolymerizing cyclic aliphatic carbonate monomers containing bromine functional groups, namely 2,2-dibromo-methyl trimethylene carbonate (DBTC) monomers or copolymerizing the 2,2-dibromo-methyl trimethylene carbonate monomers with aliphatic cyclic ester, or copolymerizing the 2,2-dibromo-methyl trimethylene carbonate monomers with the aliphatic cyclic ester or dihydroxy polyethylene glycol, or copolymerizing the 2,2-dibromo-methyl trimethylene carbonate monomers with the aliphatic cyclic ester or single methoxy polyethylene glycol; and further reacting an obtained polymer with alkylamine, thus obtaining the quaternary degradable polyester antibacterial agent with antibacterial performance. The antibacterial agent provided by the invention integrates the advantages of biocompatibility and degradability and not only has good antibacterial performance, but also has no harm to an environment, thereby being an environment-friendly antibacterial material; as an additive, the antibacterial agent provided by the invention has potential application prospects in food packaging materials, fibers, coatings, medical field and the like.

Description

technical field [0001] The invention relates to a preparation method of a quaternized degradable polyester antibacterial agent. Background technique [0002] With the improvement of living standards, people's requirements for living environment are getting higher and higher. However, there are a large number of microorganisms in nature, and harmful microorganisms have great harm to people, animals and plants, affect people's health, and even endanger their lives. For example, the shelf life of many foods is shortened due to the growth and deterioration of bacteria. If antibacterial packaging materials are developed, their storage time can be extended under certain conditions. The fiber fabric is mildewed due to the growth of bacteria, and the antibacterial fiber is prepared, which can effectively prevent the mildew of the fabric. In the medical field, with the rapid development of biomedical polymers, people can create almost all organs of the body, artificial blood vessel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N37/12A01P3/00C08G64/30C08G63/64
Inventor 朱蔚璞张秋瑾沈之荃
Owner ZHEJIANG UNIV
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