Multifunctional acrylamide compound containing capsaicin-like functional structure and preparation method and application thereof

An acrylamide and multifunctional technology, which is applied in the field of multifunctional acrylamide compounds containing capsaicinoid functional structure, can solve the problem that the price is unfeasible in scale, the steps of artificial total synthesis of capsaicin are cumbersome, and it is difficult to popularize on a large scale. use, etc.

Inactive Publication Date: 2014-07-30
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the application of capsaicin extracted from capsicum in antifouling coatings is not feasible either in terms of scale or price, and the steps of artificially fully synthesizing capsaicin are cumbersome, the yield is low, and th...

Method used

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  • Multifunctional acrylamide compound containing capsaicin-like functional structure and preparation method and application thereof
  • Multifunctional acrylamide compound containing capsaicin-like functional structure and preparation method and application thereof
  • Multifunctional acrylamide compound containing capsaicin-like functional structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Embodiment 1: the preparation of N-(2-hydroxyl-3-acrylamide methyl-4,6-dimethylbenzyl)acrylamide

[0080] Add 61.0g (0.5mol) of 3,5-xylenol and 151.5g (1.5mol) of N-methylolacrylamide (3,5- The molar ratio of xylenol to N-methylolacrylamide is 1:3), and then add 10mL of concentrated sulfuric acid catalyst (30% of the weight of 3,5-xylenol) and 50mL of ethanol solvent (for 3,5-di 64.6% of cresol weight). After stirring and reacting in a water bath at 45° C. for 24 hours, a white precipitate was formed, which was filtered with suction, and the obtained filter cake was repeatedly washed with water until neutral, and then recrystallized in absolute ethanol to obtain a white crystal.

[0081] The yield was calculated to be 87.6% according to the following formula:

[0082] (m2 is the actual obtained product quality, n1 is the amount of substance substituted with benzene compound, and M2 is the molar molecular weight of the product)

[0083] The melting point of the whit...

Embodiment 2

[0096] Embodiment 2: Preparation of N-(2-hydroxyl-3-acrylamide methyl-4,5-dimethylbenzyl)acrylamide

[0097] Add 61.0g (0.5mol) of 3,4-xylenol and 252.5g (2.5mol) of N-methylolacrylamide (3,4- The molar ratio of xylenol to N-methylolacrylamide is 1:5), and then add 5 mL of concentrated sulfuric acid catalyst (15% of the weight of 3,4-xylenol) and 70 mL of ethanol solvent (for 3,4-di 90.5% of cresol weight). After stirring and reacting in a water bath at a temperature of 50° C. for 48 hours, a white precipitate was formed, which was filtered with suction, and the obtained filter cake was repeatedly washed with water until neutral, and then recrystallized in absolute ethanol to obtain a white crystal.

[0098] Measure according to the method described in embodiment 1 and obtain following result:

[0099] The yield of the white crystal product was 88.8%, and the melting point was 206-207°C.

[0100] IR (KBr) υ / cm-1: 691.4, (benzene ring-C=C): 1545.2, 1617.2, 1639.0; (C=O): 165...

Embodiment 3

[0105] Embodiment 3: Preparation of N-(3,6-dimethyl-4-acrylamidomethyl-2-hydroxybenzyl)acrylamide

[0106] Add 61.0g (0.5mol) of 2,5-xylenol and 151.5g (1.5mol) of N-methylolacrylamide (2,5- The molar ratio of xylenol to N-methylolacrylamide is 1:3), and then add 19 mL of concentrated sulfuric acid catalyst (57% of the weight of 2,5-xylenol) and 77 mL of n-butanol solvent (for 2, 99.5% by weight of 5-xylenol). After stirring and reacting in a water bath at a temperature of 28° C. for 20 h, a white precipitate was formed, which was filtered with suction, and the obtained filter cake was repeatedly washed with water until neutral, and then recrystallized in absolute ethanol to obtain a white crystal.

[0107] Measure according to the method described in embodiment 1 and obtain following result:

[0108] The yield of the white crystal product was 88.32%, and the melting point was 179-180°C.

[0109] IR (KBr) υ / cm-1: 712.7, (benzene ring-C=C): 1465.6, 1536.2, 1621.6; (C=O): 164...

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Abstract

The invention relates to a novel multifunctional acrylamide compound containing a capsaicin-like functional structure and a preparation method and an application thereof. The compound has the chemical structure shown in the formula (I) in the specification, wherein R1, R2 or R3 represents an alkyl group, an OH group or an OCH3 substituent group. The acrylamide compound disclosed by the invention contains an important capsaicin active group as well as an active double bond capable of carrying out polymerization reaction. The synthesis method is simple and feasible, and the yield is high. The shortcomings that the amount of the natural capsaicin is limited by the complex extraction process and the pepper yield and the natural capsaicin is only used as an additive are made up. The acrylamide compound disclosed by the invention has very good application prospect in preparing the marine antifouling paint or antibacterial and antifungal coating and the viscosity of the polymer can be significantly increased when the acrylamide compound is used as a crosslinking agent.

Description

【Technical field】 [0001] The invention belongs to the technical field of acrylamide chemistry. More specifically, the present invention relates to a multifunctional acrylamide compound containing a capsaicin-like functional structure, a preparation method of the acrylamide compound, and an application of the acrylamide compound. 【Background technique】 [0002] Capsaicin is the main spicy ingredient in pepper, and its structure ( ) is an amide compound formed by fatty acid and vanillyl amine. It is a structurally stable alkaloid with antibacterial, antitumor, analgesic and anti-inflammatory effects. It has been used in medicine, health care, biological pesticides, diet, chemical industry, security defense and other technologies field. It is also reported that capsaicin is used in marine antifouling. For example, US5226380 and US5397385 disclose that capsaicin is used as an additive for antifouling coatings, which can effectively prevent the adhesion of marine fouling organ...

Claims

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Application Information

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IPC IPC(8): C07C233/20C07C231/12C09D4/02C09D5/16C09D5/14
Inventor 于良民姜晓辉李霞赵海洲闫雪峰张志明于晓琳
Owner OCEAN UNIV OF CHINA
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