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A kind of preparation method of reactive gemini quaternary ammonium salt leather fungicide

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, significant bactericidal effect and reducing tanning cost.

Active Publication Date: 2020-10-16
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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  • A kind of preparation method of reactive gemini quaternary ammonium salt leather fungicide
  • A kind of preparation method of reactive gemini quaternary ammonium salt leather fungicide
  • A kind of preparation method of reactive gemini quaternary ammonium salt leather fungicide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0029] To a 250 mL three-necked flask, 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, react at room temperature for 2~3 h, add 20 mL The excess bromoacetyl bromide was removed with distilled water, the organic phase was extracted with dichloromethane, the crude product was obtained 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]To a 250 mL three-necked flask, 0.19 g (15 mmol) of trans-1,4-dichloro-2-butene, 16.26 g (225 mmol) of diethylamine and 30 mL of solvent were added, and the reaction was carried out at 50 to 70 °C for 3 to 5 h. The precipitate was removed by filtration, and the crude product was obtained by rotary e...

Embodiment 2

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

[0036] To a 250 mL three-necked flask, add 4.84 g (24 mmol) of bromoacetyl bromide, 3.17 g (20 mmol) of n-decanol, 0.49 g (4 mmol) of catalyst and 30 mL of dichloromethane, react at room temperature for 2~3 h, add 20 mL The excess bromoacetyl bromide was removed with distilled water, the organic phase was extracted with dichloromethane, the crude product was obtained 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), 88.8% yield.

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

[0038] To a 250 mL three-necked flask, 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, and react at 50~70°C for 3~5 h , filtered to remove the precipitate, and the crude product was obtained by rotary evaporation of the filtrate, which was fu...

Embodiment 3

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

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

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

[0045] To a 250 mL three-necked flask, 0.19 g (15 mmol) of trans-1,4-dichloro-2-butene, 16.26 g (225 mmol) of diethylamine and 30 mL of solvent were added, and the reaction was carried out at 50 to 70 °C for 3 to 5 h. The precipitate was removed by filtration, and the crude produ...

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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 sterilization and anticorrosion in leather making, and in particular relates to a preparation method of a reactive gemini quaternary ammonium salt leather bactericide. Background technique [0002] The raw materials of the tanning industry come from natural animal skins. The raw hides are rich in 30% to 35% of protein and 60% to 75% of water. The raw hides provide rich nutrients for the growth and reproduction of microorganisms. Under suitable conditions, the raw hides It is easily decomposed by microorganisms and autolysase on the skin. In the process of storage and processing, it is easy to be eroded 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, the finished leather will also be contaminated by microorganisms during storage and use, resulting in the problem of bacter...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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