Quaternary bis-ammonium salt diamine fluoride and preparation method thereof

A double quaternary ammonium salt, fluorination technology, applied in chemical instruments and methods, botanical equipment and methods, preparation of organic compounds, etc., can solve the problem of poor Gram-negative bacteria effect, increased material water absorption, monoquaternary The problem of large amount of salt, etc., to achieve the effect of easy source of raw materials, good bactericidal effect, and easy control of the reaction process

Inactive Publication Date: 2008-03-26
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The problem of introducing this monoquaternary ammonium salt into polymers is: the effect on Gram-negative bacteria is extremely poor, and the amount of monoquaternary ammonium salt is large, the water absorption rate of the material increases, and even dissolves in water, so it cannot be used as a bulk material Use (Jason A. Grapski, S.L. Cooper, Synthesis and characterization of non-leaching biocidal polyurethanes, Biomaterials, 2000; 21:273-281)

Method used

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  • Quaternary bis-ammonium salt diamine fluoride and preparation method thereof
  • Quaternary bis-ammonium salt diamine fluoride and preparation method thereof
  • Quaternary bis-ammonium salt diamine fluoride and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The synthetic route is shown in the figure above.

[0040] Step 1): 4.85 grams (14mmol) of α, omega-bishydroxy tert-butoxycarbonate base lysine, 1.58 grams (15mmol) of 2-amino-2-methyl-1,3-propanediol were dissolved in 30ml N , in a mixed solvent of N-dimethylacetamide and 40ml tetrahydrofuran, add 2.94 grams (21.78 mmol) of 1-hydroxybenzotriazole, cool to 0°C with an ice bath, and then add N, N'-bicyclic 3 grams (14 mmol) of hexylcarbodiimide carbon, reacted for 24 hours, removed the precipitate by suction filtration, added 100ml of dilute hydrochloric acid, extracted with ethyl acetate, washed the organic layer with saturated sodium carbonate solution, saturated saline, and water five times, and reduced pressure Concentrate and perform silica gel column chromatography (chloroform:methanol=50:1) to obtain 4.06 g of pure lysine protected with dihydroxy tert-butoxycarbonate groups in the side chain (yield: 67%).

[0041] obtained pure 1 H-NMR (CD3Cl) δppm, 1.27 (m, 2H)...

Embodiment 2

[0051] The synthetic route is shown in the figure above.

[0052] Step 1): 4.85 grams (14 mmol) of α, ω-bishydroxy tert-butoxycarbonate base lysine, 1.58 grams (15 mmol) of 2-amino-2-methyl-1,3-propanediol, dissolved in 30 ml di In the methyl sulfoxide solvent, add 5.73 grams (16.8 mmol) of N-hydroxysuccinimide, cool to 0 ° C with an ice bath, then add 1.85 grams (14.7 mmol), reacted for 36h, removed the precipitate by suction filtration, added 100ml of dilute hydrochloric acid, extracted with ethyl acetate, and the organic layer was washed five times with saturated sodium carbonate solution, saturated brine, and water, concentrated under reduced pressure, and silica gel column chromatography (chloroform: Methanol=50:1), to obtain 4.06 g of pure lysine protected with dihydroxy tert-butoxycarbonate group in the side chain (yield: 67%).

[0053] obtained pure 1 H-NMR (CD3Cl) δppm, 1.27 (m, 2H), 1.43 (m, 23H), 1.80 (m, 2H), 3.12 (m, 2H), 3.70 (m, 3H), 3.89 (m, 2H), 4.01 (s, 2H...

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Abstract

The present invention discloses fluoric double quaternary ammonium salt diamine in the structure as shown and its preparation process. The fluoric double quaternary ammonium salt diamine has two primary amino radicals with excellent reaction activity in its structure, so that it may be introduced into polymer easily to form polymer with excellent effect of killing Gram negative bacteria. The preparation process adopts facile industrial materials and includes serial simple easy-to-control chemical reactions.

Description

technical field [0001] The invention belongs to the technical field of bisquaternary ammonium salt and its preparation, and in particular relates to a fluorinated bisquaternary ammonium salt diamine and a preparation method thereof. Background technique [0002] Since Heidelberger (Jacobs WA, Heidelberger M. The quaternary salts of hexamethylene eteramine I. Substituted benzyl halides and the hexamethylene etrammonium salts derived therefrom. J. Biol Chem. 1915; 20: 659-83; Jacobs WA, Heidelberger of M. The bacteria of quaternary prots Hexamethyleneetramine I.the problem of the chemotherapy of experimental bacterial infections.J Exp Med, 1916; 23:563-8) reported in 1915 that quaternary ammonium salts had broad-spectrum bactericidal functions, water-soluble quaternary ammonium salts were used as bactericides in various It has been widely used in the industry. Although quaternary ammonium salts (QAS) have been widely used, studies have also found that some bacteria, especiall...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C271/20C07C269/04A01N37/44A01P3/00
Inventor 钟银屏罗建斌李洁华谭鸿谢兴益何成生樊翠蓉
Owner SICHUAN UNIV
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