Benzaldehyde Schiff base type aminopyridine acetylated starch and preparation method thereof

A technology of aminopyridine acetyl and Schiff base, which is applied in the field of daily chemicals, and achieves the effects of easy promotion, simple synthesis steps, and improved reactivity

Active Publication Date: 2015-12-30
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are fewer reports on the related utilization of this renewable resource compared to other polysaccharides with higher utilization value.

Method used

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  • Benzaldehyde Schiff base type aminopyridine acetylated starch and preparation method thereof
  • Benzaldehyde Schiff base type aminopyridine acetylated starch and preparation method thereof
  • Benzaldehyde Schiff base type aminopyridine acetylated starch and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthesis route of benzaldehyde Schiff base aminopyridine acetylated starch is as follows.

[0034]

[0035] Wherein R is a halogenated phenyl group, and the average value range of n is 5-12000.

[0036] In this example, the target compound benzaldehyde Schiff base aminopyridine acetylated starch was synthesized according to the above synthetic route.

[0037] 1) Preparation of chloroacetyl starch: 1.62g starch (see figure 1 ) into 100mL of distilled water and stirred at room temperature for 20min, after adding 1.51mL of chloroacetyl chloride, reacted at room temperature for 20min, after the reaction was completed, concentrated by rotary evaporation under reduced pressure, precipitated with 50mL of absolute ethanol after cooling, suction filtered, washed, and vacuum frozen After drying, obtain product chloroacetyl starch (see figure 2 ) 1.1g, set aside.

[0038] 2) Preparation of Schiff base: first dissolve 10mmol of 4-fluorobenzaldehyde in 20mL of absolute e...

Embodiment 2

[0041] The difference from Example 1 is:

[0042] 1) Preparation of chloroacetyl starch: 1.62g starch (see figure 1 ) into 80mL of distilled water and stirred at room temperature for 40min, after adding 2.0mL of chloroacetyl chloride, reacted at room temperature for 30min, after the reaction was completed, concentrated by rotary evaporation under reduced pressure, precipitated with 30mL of absolute ethanol after cooling, suction filtered, washed, and vacuum frozen After drying, obtain product chloroacetyl starch (see figure 2 ) 1.3g, for use.

[0043] 2) Preparation of Schiff base: first dissolve 15mmol of 4-chlorobenzaldehyde in 20mL of absolute ethanol, then dissolve 10mmol of 3-aminopyridine in 10mL of absolute ethanol and slowly add it dropwise to the above-mentioned absolute ethanol solution of benzaldehyde , after it is mixed evenly, reflux and stir at 60°C for 8h, then use a rotary evaporator to spin off absolute ethanol, and finally cool, recrystallize, and freeze-dry...

Embodiment 3

[0046] The difference from Example 1 is:

[0047] 1) Preparation of chloroacetyl starch: 1.62g starch (see figure 1 ) into 100mL of distilled water and stirred at room temperature for 20min. After adding 3.02mL of chloroacetyl chloride, react at room temperature for 40min. After drying, obtain product chloroacetyl starch (see figure 2 ) 1.1g, set aside.

[0048] 2) Preparation of Schiff base: first dissolve 20mmol of 4-bromobenzaldehyde in 20mL of absolute ethanol, then dissolve 15mmol of 3-aminopyridine in 10mL of absolute ethanol and slowly add it dropwise to the above-mentioned absolute ethanol solution of benzaldehyde , after it is mixed evenly, reflux and stir at 50°C for 10h, then use a rotary evaporator to spin off absolute ethanol, and finally cool, recrystallize, and freeze-dry to obtain various Schiff bases (see Figure 5 ).

[0049] 3) 2-[4-(4-bromobenzylideneamino)-pyridinium base]-acetyl starch: 1mmol chloroacetyl starch (see figure 2 ) and 4mmol Schiff bas...

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Abstract

The invention relates to the daily chemical field and the pharmaceutical industry, in particular to benzaldehyde Schiff base type aminopyridine acetylated starch and preparation thereof. The structural formula of the benzaldehyde Schiff base type aminopyridine acetylated starch is shown as the formula (1). A preparation method comprises the following steps: firstly, starch reacts with chloroacetyl chloride, then various types of benzaldehyde react with 3-aminopyridine, Schiff bases are prepared, chloroacetyl starch reacts with the prepared Schiff bases finally, and the benzaldehyde Schiff base type aminopyridine acetylated starch shown as the formula (1) is obtained through purification, wherein the molar weight of chloroacetyl chloride is 1-2 times that of the starch, and the molar weight of various types of the Schiff bases is 2-3 times that of the chloroacetyl starch. The reaction is simple, convenient and efficient, popularization is easy, and required equipment and raw materials are easy to obtain. Research proves that the derivative has good water solubility and bacteriostatic activity, the biological activity of the starch is enhanced, the application range of the starch is enlarged, and the starch and the preparation method can be widely applied to the fields of daily chemical and pharmaceuticals.

Description

technical field [0001] The invention relates to the field of daily chemicals and the pharmaceutical industry, in particular to a benzaldehyde Schiff base aminopyridine acetylated starch and its preparation. Background technique [0002] Starch is composed of glucose molecules, which is a common component of higher plants and the main storage form of carbohydrates in cells. Starch, a biological polysaccharide, is mainly derived from crops such as corn, wheat, and potato, and is the main component of human food. There are two types of starch, amylose and amylopectin. Amylose contains hundreds of glucose units, and amylopectin contains several thousand glucose units. Starch has the advantages of being cheap and easy to obtain, and the production process is more environmentally friendly, and has good biocompatibility and degradability. However, compared with other sugars such as hyaluronic acid, heparin, and chitosan, because only Hydroxyl is an active group that lacks active ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B31/02A61P31/04A01P1/00
Inventor 郭占勇张晶晶谭文强张彩莉李婉聪王刚董方李青
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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