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Acryloyl di-quaternary ammonium salt and preparation thereof

A technology of acryloyl bisquaternary ammonium salt and purification method, which is applied in the field of quaternary ammonium salt and its preparation, and can solve the problems of lack of long-term antibacterial, poor substrate affinity, low molecular weight, etc.

Active Publication Date: 2009-01-14
ANHUI HECHEN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the diquaternary ammonium salts with high antibacterial activity have been synthesized, these synthesized diquaternary ammonium salts cannot be introduced into polymers as polymer monomers because of their molecular structure. , can only be mixed or sprayed on the treated materials, because of their low molecular weight and poor affinity with the substrate, they are easily leached or washed off during use, so they cannot achieve long-term antibacterial effect
In addition, it is necessary to introduce a side chain band into the high antibacterial activity diquaternary ammonium salt (expression general formula m-s-m) obtained by reacting dihalogenated aliphatic hydrocarbons with two to six carbon atoms and long-chain alkane tertiary amines. Reactive groups for the synthesis of antibacterial polymers, there is currently no compound that links two quaternary ammonium salt groups and has a reactive group in the side chain

Method used

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  • Acryloyl di-quaternary ammonium salt and preparation thereof
  • Acryloyl di-quaternary ammonium salt and preparation thereof
  • Acryloyl di-quaternary ammonium salt and preparation thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0050] In this example, acryloyl bis-quaternary ammonium salt (C1) was prepared.

[0051] (1) N, N, N', the preparation of N'-tetramethyl-2,6-diaminocaproic acid ethyl ester

[0052] Dissolve 24.7 grams (0.1mol) of ethyl 2,6-diaminocaproate dihydrochloride in 45 grams of 40% formaldehyde solution, then add 2.47 grams of palladium carbon, hydrogenolyze at room temperature for 12 hours, and filter Remove palladium carbon, then add 16.8 grams of sodium bicarbonate to the filtrate, remove formaldehyde by distillation under reduced pressure, extract the product with ethyl acetate and wash once with saturated saline and deionized water, dry over anhydrous sodium sulfate, and remove ethyl acetate by distillation under reduced pressure ester, namely to obtain 20.7 g of N, N, N', N'-tetramethyl-2,6-diaminocaproic acid ethyl ester with a yield of 90%.

[0053] ( 1 HNMR: 600MHz, CDCl 3 )δppm: 1.32 (3H, t, CH 3 ); 1.47~1.59 (2H, m, CH 2 ); 1.82~2.01 (4H, m, 2CH 2 ); 2.56(6H, s, 2CH ...

Embodiment 2

[0071] In this example, acryloyl bis-quaternary ammonium salt (C2) was prepared.

[0072] (1) N, N, N', the preparation of N'-tetramethyl-2,6-diaminocaproic acid ethyl ester

[0073] Because the preparation of N, N, N', N'-tetramethyl-2,6-diaminocaproic acid ethyl ester in this embodiment is exactly the same as that in Example 1, it is omitted here.

[0074] (2) Preparation of perfluorooctanoyl-2-bromoethylamine

[0075] Dissolve 41.0 grams (0.2mol) of 2-bromoethylamine hydrobromide in 250ml of deionized water, then add 33.6 grams (0.4mol) of sodium bicarbonate, lower the temperature to 0°C, and dissolve the solution in 200ml of anhydrous dichloro Add 86.6 g (0.2 mol) of methane perfluorooctanoyl chloride dropwise into 2-bromoethylamine aqueous solution, and react for 2 hours after the dropwise addition; solution, saturated sodium chloride, and deionized water, dried over anhydrous sodium sulfate, filtered, and dichloromethane was distilled off under reduced pressure to obta...

Embodiment 3

[0088] In this example, acryloyl bis-quaternary ammonium salt (C3) was prepared.

[0089] (1) 2, the preparation of 6-two (2-chloroacetamide) ethyl hexanoate

[0090] Dissolve 17.4 grams (0.1mol) of ethyl 2,6-diaminocaproate in 100ml of anhydrous dichloromethane, then add 22.2 grams (0.22mol) of triethylamine, lower the temperature to 0°C, and dissolve in 150ml Add 24.9 grams (0.22mol) of anhydrous dichloromethane (0.22mol) chloroacetyl chloride dropwise into the ethyl 2,6-diaminocaproate solution, and react for 2 hours after the dropwise addition; filter off the triethylamine salt, collect the dichloromethane layer, and Wash with dilute hydrochloric acid, saturated sodium bicarbonate solution, saturated sodium chloride, and deionized water successively, dry over anhydrous sodium sulfate, filter, and distill off dichloromethane under reduced pressure, and crystallize to obtain 2,6-bis(2-chloroacetamide ) ethyl hexanoate 31.1g, yield 95.0%.

[0091] Ms(+) theoretical: 326, 32...

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Abstract

The invention relates to an acryloyl bis-quaternary ammonium salt monomer of a side chain with a reaction active group, the monomer has the structure general formula as is shown in the formula (1) at the right side, wherein, R1 represents alkyl having 1 to 20 carbon atoms or fluorine-containing alkyl; R2 represents a covalent bond or a NHCO(CH2)t group, the t in the group is an integer from 1 to 10; R3 represents hydrogen atoms or alkyl having 1 to 5 carbon atoms; n is an integer from 0 to 10; m is an integer from 0 to 10; k is an integer from 1 to 10; Y represents alkylamine having a structural formula (2) or sec-amido-NH- or oxygen atom, wherein, R4 is alkyl having 1 to 5 carbon atoms; X is chlorine or bromine atoms; and Z is a covalent bond or an amido bond or an ester bond. The invention also provides a preparation method of the monomer. The acryloyl bis-quaternary ammonium salt provided in the invention has excellent reaction activity, and can be easily guided into the polymer to make the acquired polymer have good sterilization function, in particular to gram-negative bacterium. The method is simple and convenient, and is high in yield, and the side reaction will not take place in the reaction process.

Description

technical field [0001] The invention belongs to the technical field of quaternary ammonium salts and preparation thereof, and in particular relates to an acryloyl bisquaternary ammonium salt and a preparation method thereof. Background technique [0002] Since Heidelberger reported in 1915 that quaternary ammonium salts had broad-spectrum, low-toxicity bactericidal functions, although water-soluble single-chain quaternary ammonium salts have been widely used as bactericides in the fields of medicine, food, hygiene, etc., existing research Some bacteria, especially Gram-negative bacteria, were found to be resistant to QAS (Sopery PR, Maxey RB. Toerance of bacteria for quaternary ammonium compounds. J Food Sci, 1968; 24:141-50; Davies J. Bacteria on the rampage . Nature, 1996; 383: 219-20.). The cause of drug resistance is due to the unique cell membrane structure of Gram-negative bacteria (G-) (Jones MV, Herd TM, Christie HJ. Resistance of P. aeruginosa to amphoteric and qua...

Claims

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Application Information

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IPC IPC(8): C07C237/10C07C231/02A61K31/16A61P31/04A01N37/18A01P1/00
Inventor 谭鸿李洁华傅强谭东升
Owner ANHUI HECHEN NEW MATERIAL CO LTD
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