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Benzophenone bisamidebridged diquaternary ammonium salt type light-induced synergistic antibacterial agent and preparation method thereof

A technology of benzophenone tetracarboxylic acid diamide and benzophenone tetracarboxylic acid, which is applied in the directions of botanical equipment and methods, fungicides, biocides, etc., can solve the problems of no optical activity, poor effect, large dosage and the like , to achieve the effects of good water solubility, active oxygen generation capacity, broad-spectrum antibacterial properties, and low cost

Pending Publication Date: 2019-09-27
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by the present invention is to provide a kind of benzophenone bisamide bridging double quaternary ammonium salt type light-induced synergistic antibacterial agent and its preparation method, to overcome the antibacterial effect of the existing single antibacterial group mainly based on quaternary ammonium salt agent, make the photoactive group and the quaternary ammonium salt in the same molecule, play a joint synergistic performance, overcome the technical defects that the single quaternary ammonium salt is the main one, does not have optical activity, the dosage is large, and the effect is poor. The present invention uses N , N-dimethylalkyldiamine is the connecting unit, and the photoactive benzophenone unit is connected with the double quaternary ammonium salt unit to obtain a kind of double quaternary ammonium salt type benzophenone light-induced antibacterial agent, chemical Novel structure, synthesis

Method used

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  • Benzophenone bisamidebridged diquaternary ammonium salt type light-induced synergistic antibacterial agent and preparation method thereof
  • Benzophenone bisamidebridged diquaternary ammonium salt type light-induced synergistic antibacterial agent and preparation method thereof
  • Benzophenone bisamidebridged diquaternary ammonium salt type light-induced synergistic antibacterial agent and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0034] The present embodiment provides the synthesis (n=1) of the antibacterial agent of following structural formula:

[0035]

[0036] Its preparation method comprises the following steps:

[0037] In a 100mL three-necked flask filled with glacial acetic acid, add 3.00g of 3,3',4,4'-benzophenone tetracarboxylic dianhydride, slowly add 1.90g of N,N-dimethylpropanedi The amine was stirred continuously, and the temperature was raised to 118° C., and the reaction was completed for 5 hours.

[0038] After the reaction was completed, the acetic acid was distilled off under reduced pressure, and methanol was used as a solvent for recrystallization, separation and purification to obtain 3.45 g of the precursor compound. In a 100mL three-necked flask filled with acetone, 3.45g of precursor compound and 2.24g of benzyl chloride were added successively, stirred continuously, heated to 50°C, and reacted for 2 hours, and the reaction was complete.

[0039] After completion of the re...

Embodiment 2

[0043] The present embodiment provides the synthesis (n=1) of the antibacterial agent of following structural formula:

[0044]

[0045] Its preparation method comprises the following steps:

[0046] In a 100mL three-necked flask filled with DMF, add 3.00g of 3,3',4,4'-benzophenone tetracarboxylic dianhydride, and slowly add 1.90g of N,N-dimethylpropylenediamine at room temperature , stirring continuously, the temperature was raised to 130° C., and the reaction was carried out for 5 hours, and the reaction was complete.

[0047] After the reaction was completed, the solvent was distilled off under reduced pressure, and methanol was used as a solvent for recrystallization, separation and purification to obtain 3.05 g of the precursor compound. In a 100mL three-necked flask filled with acetone, 3.05g of precursor compound and 2.24g of benzyl chloride were successively added, stirred continuously, heated to 50°C, and reacted for 2.5 hours, and the reaction was complete.

[004...

Embodiment 3

[0050] The present embodiment provides the synthesis (n=0) of the antibacterial agent of following structural formula:

[0051]

[0052] Its preparation method comprises the following steps:

[0053] In a 100mL three-neck flask filled with glacial acetic acid, add 3.00g of 3,3',4,4'-benzophenone tetracarboxylic dianhydride, slowly add 2.37g of N,N-dimethylethanedi Amine, stirring continuously, raised the temperature to 118°C, reacted for 4 hours, and the reaction was complete.

[0054] After the reaction was completed, the acetic acid was distilled off under reduced pressure, and methanol was used as a solvent for recrystallization, separation and purification to obtain 3.40 g of the precursor compound. In a 100mL three-necked flask filled with acetone, add 3.40g of precursor compound and 2.13g of benzyl chloride successively, stir continuously, raise the temperature to 50°C, and react for 3 hours, and the reaction is complete.

[0055] After completion of the reaction, f...

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Abstract

The invention relates to a benzophenone bisamide bridged diquaternary ammonium salt type light-induced synergistic antibacterial agent and a preparation method thereof. The preparation method comprises the following steps: taking 3,3',4,4'-benzophenonetetracarboxylic dianhydride and an N,N-dimethyl fatty amine compound as raw materials, and performing a condensation reaction to obtain a benzophenonetetracarboxylic diamide compound intermediate; performing a quaternization reaction to obtain the benzophenone bisamide bridged diquaternary ammonium salt type light-induced synergistic antibacterial agent. The antibacterial agent involved in the invention has synergistic efficient antibacterial properties of a light-induced quaternary ammonium salt unit and a benzophenone bisamide unit, and has the advantages of mild reaction conditions, simple preparation process and the like at the same time.

Description

technical field [0001] The invention belongs to the field of antibacterial agents and preparation thereof, in particular to a benzophenone bisamide bridged bisquaternary ammonium salt type light-induced synergistic antibacterial agent and a preparation method thereof. Background technique [0002] People will inevitably come into contact with various microorganisms in daily life. Because the surface of textiles, household items and other materials has a certain roughness and more microporous structure, bacteria can easily breed and transfer to the surface of the skin, which is harmful to the human body. serious health hazard. Therefore, in recent years, research on antibacterial agents and antibacterial materials has received extensive attention. Antibacterial agents are mainly divided into inorganic nano-antibacterial agents, organic antibacterial agents and natural antibacterial agents. Inorganic nanomaterials have a small size effect and excellent photochemical activity...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48A01N43/38A01N59/00A01P3/00A01P1/00
CPCC07D209/48A01N43/38A01N59/00
Inventor 谢孔良胡柳高爱芹侯爱芹
Owner DONGHUA UNIV
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