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A photoresponsive interpenetrating network polymer based on coumarin and its preparation method

An interpenetrating network and hydroxycoumarin technology, which is applied in the field of preparation of functional polyacrylate emulsions, can solve problems such as changing the interpenetrating network of polymers, and achieve the effects of excellent mechanical properties, improved mechanical properties, and improved fluidity.

Inactive Publication Date: 2018-03-30
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the design and preparation method of the polymer interpenetrating network has not been changed by illumination, so polymers that combine photoresponsive properties and interpenetrating network properties are a direction of research in this paper

Method used

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  • A photoresponsive interpenetrating network polymer based on coumarin and its preparation method
  • A photoresponsive interpenetrating network polymer based on coumarin and its preparation method
  • A photoresponsive interpenetrating network polymer based on coumarin and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: (1) take by weighing 4.864g (0.030mol) 4-hydroxycoumarin, 3.036g (0.030mol) triethylamine, be dissolved in the 100ml there-necked flask containing 50ml dichloromethane, ice-water bath, dropwise 2.715g (0.030mol) of acryloyl chloride for 1 hour, react at 18°C ​​for 4 hours after dropping, filter, and rotary steam at 25°C to remove dichloromethane, dissolve the product in absolute ethanol for recrystallization, add 30ml of 0.1mol / l hydrochloric acid to the product and wash once , washed once with 30ml of 5% (mass percentage concentration) aqueous sodium hydroxide solution, washed twice with 30ml of deionized water, and dried in a vacuum oven at 30°C to obtain 5.652g of coumarin acrylate, with a yield of 75%;

[0029] Product Coumarin Acrylate 1 H NMR (400MHz, CDCl 3 ) data are: δ7.39(s, 1H), δ7.30(d, 1H), δ7.65(d, 1H), δ7.97(d, 1H), δ6.12(d, 1H), δ6 .10(dd, 1H), δ6.24(dd, 1H), δ5.74(dd, 1H);

[0030] (2) Weigh 2.161g (0.010mol) coumarin acrylate, 2.002g (...

Embodiment 2

[0032] Embodiment 2: (1) take by weighing 4.864g (0.030mol) 4-hydroxycoumarin, 3.036g (0.030mol) triethylamine, be dissolved in the 100ml there-necked flask containing 50ml ethyl acetate, ice-water bath, dropwise 2.715g (0.030mol) of acryloyl chloride for 1 hour, react at 30°C for 4h after dropping, filter, and rotary steam at 25°C to remove dichloromethane, dissolve the product in absolute ethanol for recrystallization, add 30ml of 0.1mol / l hydrochloric acid to the product and wash once , washed once with 30ml of 5% sodium hydroxide aqueous solution, washed twice with 30ml of deionized water, and dried in a vacuum oven at 30°C to obtain 5.889g of coumarin acrylate, with a yield of 78%;

[0033] (2) Weigh 4.323g (0.020mol) coumarin acrylate, 1.502g (0.015mol) methyl methacrylate, 8.972g (0.07mol) butyl acrylate, 1.562g (0.01mol) styrene, 0.491g Emulsifier didodecyl phenyl ether sodium disulfonate (monomer mass 3wt%), 0.491g stearyl alcohol (monomer mass 3wt%), be dissolved in ...

Embodiment 3

[0035] Embodiment 3: (1) take by weighing 4.864g (0.030mol) 4-hydroxycoumarin, 3.339g (0.033mol) triethylamine, be dissolved in the 100ml there-necked flask containing 50ml acetone, ice-water bath, dropwise add 2.715g (0.030mol) acryloyl chloride for 1 hour, react at 28°C for 4 hours after dropping, filter, and rotary steam at 25°C to remove dichloromethane, dissolve the product in absolute ethanol for recrystallization, add 30ml of 0.1mol / l hydrochloric acid to the product, wash once, 30ml Wash once with 5% sodium hydroxide aqueous solution, wash twice with 30ml deionized water, and dry in a vacuum oven at 30°C to obtain 5.540g of coumarin acrylate with a yield of 73%;

[0036] (2) Weigh 4.323g (0.020mol) coumarin acrylate, 1.001g (0.01mol) methyl methacrylate, 10.254g (0.08mol) butyl acrylate, 1.041g (0.01mol) styrene, 0.499g Emulsifier sodium dodecylbenzenesulfonate (monomer mass 3wt%), 0.499g stearyl alcohol (monomer mass 3wt%), be dissolved in the 250ml beaker containing ...

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Abstract

A photoresponsive interpenetrating network polymer based on coumarin and a preparation method thereof belong to the field of preparation of functional polyacrylate emulsions. Molecules containing groups such as coumarin and cinnamic acid will undergo cycloaddition reactions under the irradiation of ultraviolet light of different wavelengths, causing chain crosslinking and breaking. The present invention grafts acrylate groups on hydroxycoumarin, and forms coumarin polyacrylates with coumarin groups in side chains through emulsion polymerization with acrylate monomers, and then makes them cross-linked by light. Forms photodegradable cross-linked polyacrylate polymers. Taking the formed cross-linked polyacrylate polymer emulsion as a seed, adding a cross-linking agent and a monomer to the emulsion to swell the polyacrylate polymer molecules, and adding an initiator to form an interpenetrating network polymer. This interpenetrating network polymer will degrade and crosslink again through the cycloaddition reaction of coumarin groups under specific ultraviolet light irradiation, thereby changing the molecular structure to meet different needs.

Description

technical field [0001] The invention relates to the preparation of light-responsive polyacrylic acid cross-linked emulsion microspheres, and belongs to the field of preparation of functional polyacrylate emulsions. Background technique [0002] Photoresponsive materials have been widely used in the field of materials due to their convenience, sensitivity and simplicity. Coumarin has excellent optical properties, and molecules with coumarin groups have excellent photoresponsive properties. Under different wavelengths of ultraviolet light, such molecules have the structural characteristics of chain crosslinking and breaking, which makes it possible to Adapt to the needs of different applications. [0003] The seed emulsion swelling polymerization method is to add the monomer into the seed emulsion, swell at a certain temperature for a period of time, and then increase the temperature to the reaction temperature and then add an initiator to carry out polymerization. In this p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F220/18C08F220/14C08F212/08C08F220/30C08F265/06C08F222/14
CPCC08F220/18C08F265/06C08F220/1804C08F220/14C08F212/08C08F220/302C08F222/14
Inventor 聂俊白美荣朱晓群方大为
Owner BEIJING UNIV OF CHEM TECH
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