Guanidyl modified quaternary ammonium salt and synthetic method thereof

A synthesis method and technology of quaternary ammonium salts are applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve the effects of strong positive electricity, high antibacterial activity and significant bactericidal effect

Active Publication Date: 2014-01-08
CHINA RES INST OF DAILY CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no report on this type of surfactant

Method used

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  • Guanidyl modified quaternary ammonium salt and synthetic method thereof
  • Guanidyl modified quaternary ammonium salt and synthetic method thereof
  • Guanidyl modified quaternary ammonium salt and synthetic method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Embodiment 1: the synthesis of N,N-dimethyl-N-guanidine propyl n-octyl quaternary ammonium salt

[0031] Add 5.1g (0.05mol) of N,N-dimethylpropylenediamine and 50g of absolute ethanol into a 250ml four-necked flask, and slowly add 9.7g (0.05mol) of n-bromooctane dropwise under stirring at room temperature. ), after 30min dropwise addition, continue to stir for 1h, then heat up and reflux for 4h, distill off ethanol under reduced pressure, wash with ether twice, add acetone 30g, hydrobromic acid (content 10%) to pH = 4, drop Add 5.1 g of cyanamide solution (50% aqueous solution), reflux for 2 hours, remove acetone under reduced pressure, and recrystallize to obtain the product N,N-dimethyl-N-guanidinepropyl n-octyl quaternary ammonium salt with a yield of 74%.

[0032] Infrared spectrum ( KBr, cm -1 ): 3366, 3280, 2936, 2857, 1646(C=N, st) (C=N, st) (C=N, st) (C=N, st), 1406(N-H, δ), 1114(C –N–C, δ), 721.

[0033] Proton NMR spectrum (400MHz, D 2 O), δ / ppm, 0.82(t, 3...

Embodiment 2

[0036] Embodiment 2: the synthesis of N,N-dimethyl-N-(dimethylguanidine-propyl) n-decyl quaternary ammonium salt

[0037] Add 5.1g (0.05mol) of N,N-dimethylpropylenediamine and 30g of n-propanol into a 250ml four-necked flask, and slowly add 11.1g of n-bromodecane dropwise under stirring at room temperature for 20min. After the addition is complete, continue to stir and react for 0.5 h, raise the temperature and reflux for 6 h, distill off the solvent under reduced pressure, wash with diethyl ether twice, then adjust the pH to 3 with 50 g of acetone and hydrobromic acid (content 30%), add 5.3 g of N, N -Dimethylcyanamide, reflux for 5h, remove the solvent under reduced pressure, and recrystallize to obtain the product methyl-substituted guanidinyl dimethyl n-decyl quaternary ammonium salt, with a yield of 82%.

[0038] Infrared spectrum ( KBr, cm -1 ): 3419, 2925, 2856, 1646, 1406, 1114, 721.

[0039] Proton NMR spectrum (400MHz, D 2 O), δ / ppm, 0.85(t, 3H, CH3 ), 1.27 (br...

Embodiment 3

[0042] Embodiment 3: the synthesis of N,N-dimethyl-N-guanidine propyl dodecyl quaternary ammonium salt

[0043] Add 5.1g (0.05mol) of N,N-dimethylpropylenediamine and 30g of isopropanol into a 250ml four-necked flask, and slowly add 12.5g of bromododecane dropwise under stirring at room temperature for 80 min After the dropwise addition is completed, continue to stir for 2 hours, then heat up to reflux for 8 hours, distill off the solvent under reduced pressure, wash with ether twice, add acetone, adjust the pH to 2 with hydrobromic acid (content 10%), add 6.3 g of cyanamide solution dropwise (50% aqueous solution), reflux for 6 hours, remove the solvent under reduced pressure, and recrystallize from ethanol to obtain the product N,N-dimethyl-N-guanidinepropyl dodecyl quaternary ammonium salt with a yield of 87%.

[0044] Infrared spectrum ( KBr, cm -1 ): 3366, 3280, 2925, 2856, 1646, 1406, 1114, 721.

[0045] Proton NMR spectrum (400MHz, D 2 O), δ / ppm, 0.84(t, 3H, CH3), 1....

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Abstract

The invention relates to a guanidyl modified quaternary ammonium salt which has a following structural formula, wherein R1 is C8-C12 saturated straight-chain paraffin; R2 is equal to H or R1; and R3 is equal to H or CH3. The guanidyl modified quaternary ammonium salt has the advantages of higher positive electricity, obvious sterilizing effect, excellent killing effect special for fungus, excellent water solubility and excellent compounding property.

Description

technical field [0001] The invention belongs to a surfactant and a synthesis method thereof, in particular to a guanidine-modified quaternary ammonium salt and a synthesis method thereof. Background technique [0002] Since Domagk discovered the bactericidal effect of alkyl dimethyl ammonium chloride in 1935, quaternary ammonium salt fungicides have successively experienced alkyl dimethyl ammonium halides, double long-chain quaternary ammonium salts, Gemini quaternary ammonium salts and some modifications. product, its surface activity and bactericidal activity are all significantly improved. For example, Chinese patent CN101165045A has reported dialkyl methyl hydroxyethyl quaternary ammonium salt and its synthetic method, CN1973625A has reported pyridine quaternary ammonium salt and its synthetic method, and CN1115328C has reported hydroxyl and amino modified quaternary ammonium salt and its synthetic method . The research work on modified quaternary ammonium salt surfact...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C279/12C07C277/08B01F17/18A01P3/00C09K23/18
Inventor 宋永波李秋小李运玲
Owner CHINA RES INST OF DAILY CHEM IND
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