Sulfated chitosan quaternary ammonium salt as well as preparation and application thereof

A technology of chitosan quaternary ammonium salt and esterified chitosan is applied in the field of daily chemicals to achieve the effect of improving antioxidant activity and improving biological activity

Inactive Publication Date: 2014-03-26
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] But at this stage there is no relevant report about sulfated chitosan quaternary ammonium salt

Method used

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  • Sulfated chitosan quaternary ammonium salt as well as preparation and application thereof
  • Sulfated chitosan quaternary ammonium salt as well as preparation and application thereof
  • Sulfated chitosan quaternary ammonium salt as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Sulfated chitosan quaternary ammonium salt is the compound shown in (Formula 1)

[0028]

[0029] Synthesis of sulfated chitosan quaternary ammonium salt:

[0030] Mix 0.6g 2,2,2-trimethyl chitosan quaternary ammonium salt (refer to the literature Bioorganic & Medicinal Chemistry Letters 16, 2006, 63, 48-6350 for preparation method) and 10mL N,N-dimethylformamide (DMF) solution , Stir at a rate of 200-300r / min in a water bath at 30°C for 20min, then slowly add 15mL of sulfonation reagent (chlorosulfonic acid) dropwise while stirring at a rate of 200-300r / min / DMF, the preparation method refers to the literature: Chemical Technology and Development, 2008, 37, 15-17), stirred and reacted in a water bath at 30°C for 3h, cooled at room temperature, then precipitated with absolute ethanol, stood for 30min to filter, and washed with absolute ethanol After suction filtration and drying, 3,6-disulfate-2,2,2-trimethyl chitosan quaternary ammonium salt was obtained. For its ...

Embodiment 2

[0033] The difference from Example 1 is:

[0034] 0.6g 2-ethyl-2,2-dimethyl chitosan quaternary ammonium salt (for the preparation method, refer to the literature Bioorganic & Medicinal Chemistry Letters 16, 2006, 63, 48-6350) and 10mL N,N-dimethylformamide (DMF) The solutions were mixed, stirred at a rate of 200-250r / min in a water bath at 43°C for 20min, and then slowly added dropwise while stirring at a rate of 200-250r / min (dropping rate of 10-15 drops / min) 12mL of sulfonated reagent ( Chlorosulfonic acid / DMF=1:5), stirred and reacted in 43°C water bath for 2h, cooled at room temperature, then precipitated with absolute ethanol, stood for 30min to filter, washed with absolute ethanol, and dried by suction to obtain 3,6- Disulfate-2-ethyl-2,2-dimethyl chitosan quaternary ammonium salt. For its infrared spectrum, see Figure 5 .

[0035] From Figure 5 can be known with Figure 4 Compared to 1226.51cm -1 It is the vibration absorption peak of sulfuric acid, 802.24cm -...

Embodiment 3

[0037] The difference from Example 1 is:

[0038] 0.6g 2-salicylaldehyde-2,2-dimethyl chitosan quaternary ammonium salt (for the preparation method refer to the literature Bioorganic & Medicinal Chemistry Letters 16,2006,63,48-6350) and 10mL N,N-dimethylformamide (DMF) Mix the solutions, stir in a 60°C water bath at a rate of 200-250r / min for 5min, then slowly add 10mL of sulfonation reagent (chlorosulfonic acid / DMF=1:5) dropwise while stirring, stir and react in a 60°C water bath for 1.5h, Cool at room temperature, then precipitate with absolute ethanol, let it stand for 30 minutes to filter, wash with absolute ethanol, filter and dry to obtain 3,6-disulfate-2-salicylaldehyde-2,2-dimethyl chitosan Sugar quaternary ammonium salt. For its infrared spectrum, see Figure 7 .

[0039] From Figure 7 can be known with Figure 6 Compared to 1226.51cm -1 Vibration absorption peak for sulfuric acid, 796.82cm -1 It is the C-O-S stretching vibration absorption peak, which can pro...

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Abstract

The invention relates to the fields of daily use chemicals and pharmaceuticals industry and in particular relates to a sulfated chitosan quaternary ammonium salt as well as a preparation and an application thereof. The sulfated chitosan quaternary ammonium salt is shown as a formula (1). The preparation method specifically comprises the following steps: uniformly mixing chitosan quaternary ammonium salt and an N,N-dimethyl formamide (DMF) solution, slowly dropwise adding a sulfonated reagent under the stirring condition after uniformly mixing, reacting in a water bath at the temperature of 30-60 DEG C for 1.5-3 hours, cooling at room temperature, performing absolute ethyl alcohol precipitation, filtering, washing by using absolute ethyl alcohol, and drying to obtain the sulfated chitosan quaternary ammonium salt. The obtained sulfated chitosan quaternary ammonium salt is easily dissolved in water; due to introduction of sulfonate, the biological activity of the chitosan quaternary ammonium salt is enhanced, and a synergistic effect is achieved, so that the sulfated chitosan quaternary ammonium salt has higher biological activity and can be widely applied to the fields of medicines and daily use chemicals.

Description

technical field [0001] The invention relates to the field of daily chemicals and the pharmaceutical industry, in particular to a sulfated chitosan quaternary ammonium salt and its preparation and application. Background technique [0002] Reactive oxygen free radicals have a huge damage effect on the body, such as causing protein damage, enzyme inactivation, membrane peroxidation, leading to aging, tumors, atherosclerosis and many other diseases. Therefore, it is of great significance to screen active oxygen scavengers that are safe and efficient for the human body. [0003] Chitosan (Chitosan) is a renewable, non-toxic and side-effect-free natural amino polysaccharide with good biocompatibility and degradability that widely exists in nature. It itself and its quaternary ammonium salt have many unique physiological and pharmacological functions. It is widely used in various industries such as medicine, food, agriculture, daily chemical, and environmental protection. Chitos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A61P39/06A61P17/18A61K8/73A61Q19/08
Inventor 王刚董方李青郭占勇
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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