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Preparation method of reactive gemini quaternary ammonium salt leather bactericide

A technology of gemini quaternary ammonium salt and bactericide is applied in the field of preparation of reactive gemini quaternary ammonium salt leather bactericide, can solve problems such as high toxicity, and achieve the effect of promoting bactericidal effect, easy biodegradation and good water solubility

Active Publication Date: 2018-03-16
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the other hand, most of the fungicides and fungicides used for finished leather are commonly used fungicides and fungicides on the market. At present, the most commonly used fungicide is 2-thiocyanomethylthiobenzothiazole (TCMTB). The fungicide is a sulfur compound, which is highly toxic

Method used

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  • Preparation method of reactive gemini quaternary ammonium salt leather bactericide
  • Preparation method of reactive gemini quaternary ammonium salt leather bactericide
  • Preparation method of reactive gemini quaternary ammonium salt leather bactericide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Preparation of n-octyl bromoacetate:

[0029] Add 4.84 g (24 mmol) of bromoacetyl bromide, 2.61 g (20 mmol) of n-octanol, 0.49 g (4 mmol) of catalyst and 30 mL of dichloromethane into a 250 mL three-neck flask, react at room temperature for 2-3 h, add 20 mL Distilled water to remove excess bromoacetyl bromide, extracted the organic phase with dichloromethane, obtained the crude product by rotary evaporation of the organic phase, and further purified by flash column chromatography (petroleum ether: ethyl acetate = 20:1) to obtain n-octyl bromoacetate (4.37 g), 87% yield.

[0030] (2) Preparation of trans-N,N,N',N'-tetraethyl-2-butene-1,4-diamine

[0031]Add 0.19 g (15 mmol) of trans-1,4-dichloro-2-butene, 16.26 g (225 mmol) of diethylamine and 30 mL of solvent into a 250 mL three-necked flask, react at 50~70°C for 3~5 h, filter The precipitate was removed, and the crude product was obtained by rotary evaporation of the filtrate, which was further purified by flash ...

Embodiment 2

[0035] (1) Preparation of n-decyl bromoacetate:

[0036] Add 4.84 g (24 mmol) of bromoacetyl bromide, 3.17 g (20 mmol) of n-decyl alcohol, 0.49 g (4 mmol) of catalyst and 30 mL of dichloromethane into a 250 mL three-necked flask, react at room temperature for 2-3 h, add 20 mL Distilled water to remove excess bromoacetyl bromide, extracted the organic phase with dichloromethane, obtained the crude product by rotary evaporation of the organic phase, and further purified by flash column chromatography (petroleum ether: ethyl acetate = 20:1) to obtain n-decyl bromoacetate (4.96 g), yield 88.8%.

[0037] (2) Preparation of trans-N,N,N',N'-tetraethyl-2-butene-1,4-diamine

[0038] Add 0.19 g (15 mmol) of trans-1,4-dichloro-2-butene, 16.26 g (225 mmol) of diethylamine and 30 mL of solvent into a 250 mL three-necked flask, react at 50~70°C for 3~5 h, The precipitate was removed by filtration, and the crude product was obtained by rotary evaporation of the filtrate, which was further ...

Embodiment 3

[0042] (1) Preparation of n-dodecyl bromoacetate:

[0043] Add 4.84 g (24 mmol) of bromoacetyl bromide, 3.73 g (20 mmol) of n-dodecyl alcohol, 0.49 g (4 mmol) of catalyst and 30 mL of dichloromethane solvent into a 250 mL three-necked flask, and react at room temperature for 2-3 h. Add 20 mL of distilled water to remove excess bromoacetyl bromide, extract the organic phase with dichloromethane, obtain the crude product by rotary evaporation of the organic phase, and further purify by flash column chromatography (petroleum ether: ethyl acetate = 20:1) to obtain bromoacetic acid N-dodecyl ester (5.47 g), yield 89%.

[0044] (2) Preparation of trans-N,N,N',N'-tetraethyl-2-butene-1,4-diamine

[0045] Add 0.19 g (15 mmol) of trans-1,4-dichloro-2-butene, 16.26 g (225 mmol) of diethylamine and 30 mL of solvent into a 250 mL three-necked flask, react at 50~70°C for 3~5 h, filter The precipitate was removed, and the crude product was obtained by rotary evaporation of the filtrate, wh...

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Abstract

The invention discloses a preparation method of a reactive gemini quaternary ammonium salt leather bactericide. The preparation method comprises the following three steps: first step, carrying out esterification reaction on bromoacetyl bromide and fatty alcohol to generate bromine acetate; second step, carrying out nucleophilic substitution on trans-1,4-dichloro-2-butene and diethylamine to generate trans-N,N,N',N'-tetraethyl-2-butene-1,4-diamine; and third step, carrying out quaterisation on products obtained from the first two steps to obtain a reactive gemini quaternary ammonium salt. The preparation method is easy to operate, the yield of products is high, the cost of raw materials is low, the practicality is high, and moreover, a method for synthesizing diamine intermediate in the second step provides a new thinking and new method for synthesis of the gemini quaternary ammonium salt. Owing to existing of prepared bactericide molecular structure ester groups, the sterilizing property is improved, and biodegradability can be good. In addition, owing to existing of active groups C=C in the structure, the chemical activity of the gemini quaternary ammonium salt is improved, the gemini quaternary ammonium salt can be further chemically bounded into skin collagen and leather coating resin materials, and the long-lasting sterilizing property can be achieved.

Description

technical field [0001] The invention belongs to the technical field of tanning, sterilization and anticorrosion, and in particular relates to a preparation method of a reactive geminiquaternary ammonium salt leather bactericide. Background technique [0002] The raw materials of the tanning industry come from natural animal hides, which are rich in 30%~35% protein and 60%~75% moisture. Raw hides provide rich nutrients for the growth and reproduction of microorganisms. Under suitable conditions, raw hides It is easily rotted by microorganisms and autolytic enzymes on the hide. In the process of storage and processing, it is easy to be corroded by various harmful bacteria and rot and deteriorate. In order to inhibit the growth and reproduction of harmful bacteria, it is often necessary to add certain fungicides. In addition, during the storage and use of finished leather, it will also be polluted by microorganisms, and there will be problems of mold and mildew. At present, t...

Claims

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Application Information

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IPC IPC(8): C07C229/16C07C227/02C07C67/14C07C69/63C07C209/08C07C211/22A01N37/44A01P1/00A01P3/00
CPCA01N37/44C07C67/14C07C209/08C07C227/02C07C69/63C07C211/22C07C229/16
Inventor 林炜张龙王春华谷新林
Owner SICHUAN UNIV
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