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Quaternary ammonium salt polymer as well as preparation method and application thereof

A technology of quaternary ammonium salts and polymers, which is applied in the field of preparation of quaternary ammonium salt polymers, and can solve the problems of skin irritation and general antibacterial properties of quaternary ammonium salts

Active Publication Date: 2021-06-08
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Hexatropine can be used as a raw material for organic synthesis, antibiotics, fuel, etc. Currently, related reports mainly include synthesizing quaternary ammonium salts with hexatropine as a parent and halogenated substances (F, Cl, Br, I), such as in Org Process Rajesh T in Res Dev, 2009, 13, 638-640 reported that by using dichloromethane as a solvent, heating to reflux to obtain hexamethamine quaternary ammonium salt, and Narayan in Eur.J.Med.Chem., 2019, 161, 456-467 S has reported that the method for synthesizing urotropine quaternary ammonium salt is to use urotropine and halogenated alkanes as raw materials, reflux 6-9h in methylene chloride, obtain quaternary ammonium salt product, the quaternary ammonium salt that above-mentioned method obtains is to skin Some irritation, and general antibacterial properties
And further improving urotropine to improve its antibacterial activity has not been reported

Method used

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  • Quaternary ammonium salt polymer as well as preparation method and application thereof
  • Quaternary ammonium salt polymer as well as preparation method and application thereof
  • Quaternary ammonium salt polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1: synthetic quaternary ammonium salt monomer 1

[0051] Add 9.03g (0.064mol) of urotropine and 7.74g (0.064mol) of allyl bromide into a 250ml round bottom flask, then add 135ml of chloroform solvent, and heat to 60°C to reflux. After reacting for 8 hours, turn off heating and stirring, cool to room temperature, filter, wash with chloroform (20ml×3), and dry in a vacuum oven for 1 hour to obtain 15.84g of quaternary ammonium salt monomer 1 with a yield of 95%.

[0052] The reaction formula of the above process is expressed as follows:

[0053]

[0054] The NMR spectrum of the product is as figure 1 , 3 shown.

[0055] 1 H-NMR (D 2 O,400MHz)δ:5.85(1H,m,H-12),5.62(2H,dd,J=22.2,13.4Hz,H-13),5.01(6H,s,H-7,8,9), 4.63(3H,d,J=12.9Hz,H-2,4,6),4.47(3H,d,J=12.7Hz,H-2',4',6'),3.46(2H,d,J =7.5Hz,H-11,11'); 13 C-NMR (D 2 (0, 100MHz) δ: 129.64 (C-12), 121.49 (C-13), 77.86 (C-7, 8, 9), 69.99 (C-2, 4, 6), 59.17 (C-11).

[0056] Replacement example 1

[0057] Th...

Embodiment 2

[0062] Embodiment 2: synthetic quaternary ammonium salt monomer 2

[0063] Add 9.03g (0.064mol) urotropine and 6.82g (0.061mol) 1,3-dichloropropene into a 250ml round bottom flask, then add 135ml chloroform solvent, heat to 60°C and reflux. After reacting for 8 hours, turn off heating and stirring, cool to room temperature, filter, wash with chloroform (20ml×3), and dry in a vacuum oven for 1 hour to obtain 14.94g of quaternary ammonium salt monomer 2 with a yield of 97%.

[0064] The reaction formula of the above process is expressed as follows:

[0065]

[0066] The NMR spectrum of the product is as figure 2 , 4 shown.

[0067] 1 H-NMR (D 2 O,400MHz)δ:6.74(1H,dd,J=44.0,12.0Hz,H-13),6.045(1H,m,H-12),5.08(6H,d,J=24.1Hz,H-7, 8,9),4.56(6H,m,H-2,4,6),3.62(2H,dd,J=57.0,7.7Hz,H-11,11'); 13 C-NMR (D 2 (0, 100MHz) δ: 131.63 (C-12), 116.5 (C-13), 78 (C-7, 8, 9), 69.95 (C-2, 4, 6), 54.04 (C-11).

Embodiment 3

[0069] Get quaternary ammonium salt monomer 1 9.97g (0.038mol) that has been synthesized in embodiment 1, 4.95g (0.038mol) 1,4-divinylbenzene joins in the 500ml conical flask, then adds 250ml ethanol solvent, 0.16 g of azobisisobutyronitrile, stirred at room temperature for 1 hour, transferred to a reaction kettle, and reacted at 110°C. After reacting for 12 hours, turn off the heating and stirring, cool to room temperature, filter to obtain a solid powder polymer, wash with ethyl acetate (20ml×3), and dry in a vacuum oven for 1 hour to obtain 11.64g of quaternary ammonium salt polymer. was 78%.

[0070] The reaction formula of the above process is expressed as follows:

[0071]

[0072] The infrared spectrum of the product is shown in Figure 5 Shown: IR(cm -1 ) 1402, 1681, 3166, 3430.

[0073] Replacement example 3

[0074] The preparation method of replacement examples 3-1 to 3-17 is the same as that of Example 3, the difference is that the reaction temperature, dif...

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Abstract

The invention provides a quaternary ammonium salt polymer and a preparation method and application thereof, and belongs to the technical field of ammonium salt preparation through chemical modification. The quaternary ammonium salt polymer is prepared by taking urotropine and halogenated alkene as initial raw materials, carrying out reflux reaction in an effective solvent, and then carrying out cross-linking reaction with a second monomer and azodiisobutyronitrile. The quaternary ammonium salt polymer disclosed by the invention is applied to a bactericide, has an excellent bactericidal effect on bacteria such as escherichia coli, is easy to separate and can be repeatedly utilized.

Description

technical field [0001] The application relates to a preparation method and application of a quaternary ammonium salt polymer, and belongs to the technical field of ammonium salt preparation through chemical modification. Background technique [0002] Quaternary ammonium compounds are widely used as a highly effective antibacterial agent in water treatment, medical and health care, packaging materials and other fields. Small molecule quaternary ammonium antibacterial agents have the disadvantages of being volatile, difficult to process, and poor in chemical stability. After being prepared into high-molecular quaternary ammonium salt polymers, they have better antibacterial properties and are also non-volatile and chemically stable. Good sex, low toxicity, environmental friendliness and so on. Hexatropine can be used as a raw material for organic synthesis, antibiotics, fuel, etc. Currently, related reports mainly include synthesizing quaternary ammonium salts with hexatropin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F226/06C08F212/36C08F222/38C08F212/08C07D487/18A01N43/90A01P1/00
CPCC08F226/06C07D487/18A01N43/90C08F212/36C08F222/385C08F212/08
Inventor 刘小睿沈永淼冯传威王丹燕曹画画
Owner ZHEJIANG SCI-TECH UNIV
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