Compound type macromolecular light stabilizer based on Diels-Alder click chemistry and preparation method thereof

A technology of light stabilizer and click chemistry, which is applied in the field of compound macromolecular light stabilizer and its preparation, can solve problems such as human health threats, achieve good compatibility, excellent broad-spectrum ultraviolet absorption function, and mild reaction conditions Effect

Active Publication Date: 2017-04-26
江苏多淇医疗设备有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in recent years, it has been found that low-molecular light stabilizers have a high accumulation in biota, which poses a threat to human health.

Method used

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  • Compound type macromolecular light stabilizer based on Diels-Alder click chemistry and preparation method thereof
  • Compound type macromolecular light stabilizer based on Diels-Alder click chemistry and preparation method thereof
  • Compound type macromolecular light stabilizer based on Diels-Alder click chemistry and preparation method thereof

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preparation example Construction

[0027] The invention provides a compound type macromolecular light stabilizer based on Diels-Alder click chemistry and a preparation method thereof, comprising: utilizing 3-(N, N,-2-maleimido ethyl propionate-amine Diels-Alder reaction of methyl)-2,4-dihydroxybenzophenone and bisfurfuryl sebacate as raw material monomers, and then adding 2,2,6,6-tetramethylpiperidinol maleyl The imine propionate is used as an end-capping agent to carry out end-capping to prepare a composite macromolecular light stabilizer, wherein the addition amount of the end-capping agent is 0.1-2% of the total weight of the raw material monomers.

[0028] The molecular chain of the composite macromolecular light stabilizer prepared by the preparation method of the compound macromolecular light stabilizer based on Diels-Alder click chemistry of the present invention is a heterochain, which has excellent broad-spectrum ultraviolet absorption function; Different end-capping agents can be used for chain end gr...

Embodiment 1

[0039] (1) Synthesis of 3-(N, N,-2-hydroxyethyl-aminomethyl)-2,4-dihydroxybenzophenone (HAHBP)

[0040] UV-0: diethanolamine=1: 1.2 (mol); UV-0: paraformaldehyde=1: 1.4 (mol),

[0041] Put 1.26g (0.012mol) of diethanolamine into a 150mL three-necked flask, and start to add 0.42g (0.014) of paraformaldehyde powder in batches when heating at 60°C, and put in 0.14g of paraformaldehyde every 15 minutes, and put it in 3 batches. After the addition, the temperature was raised to 70°C for 1.0 h, then 2.14 g (0.01 mol) of UV-0 was dissolved in 8 mL of methanol, added to the above reaction solution, and the reaction was continued at 70°C for 2.5 h. Then the product is washed with water to remove excess diethanolamine and paraformaldehyde, freeze-dried, and the synthetic route is:

[0042]

[0043] (2) Synthesis of 3-(N,N,-2-ethyl maleimidopropionate-aminomethyl)-2,4-dihydroxybenzophenone (EMIPAHBP)

[0044] MIPA:HAHBP=2.0:1, MIPA:DCC=1:1 (mol).

[0045] In a 150mL three-necked fl...

Embodiment 2

[0059] (1) Synthesis of 3-(N, N,-2-hydroxyethyl-aminomethyl)-2,4-dihydroxybenzophenone (HAHBP)

[0060] UV-0: diethanolamine=1: 2.0 (mol): UV-0: paraformaldehyde=1: 1.5 (mol),

[0061] Put 2.23g (0.0212mol) of diethanolamine into a 150mL three-necked flask, and start adding paraformaldehyde powder in batches at 70°C, a total of 0.99g (0.033mol), and put in 0.2475g of paraformaldehyde every 15min, and put it in 4 batches After the addition, the temperature was raised to 80°C for 2.5h, and then 2.27g (0.0106mol) of UV-0 was dissolved in 15mL of methanol, added to the above reaction solution, and kept at 80°C for 5h. Then the product is washed with water to remove excess diethanolamine and paraformaldehyde, freeze-dried (vacuum-dried), and the synthetic route is:

[0062]

[0063] (2) Synthesis of 3-(N,N,-2-ethyl maleimidopropionate-aminomethyl)-2,4-dihydroxybenzophenone (EMIPAHBP)

[0064] MIPA:HAHBP=2.5:1, MIPA:DCC=1:1 (mol).

[0065] In a 150mL three-necked flask, add 2....

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Abstract

The invention discloses a preparation method of a compound type macromolecular light stabilizer based on Diels-Alder click chemistry. The preparation method comprises the following steps: performing a Diels-Alder reaction by using 3-(N,N-2-maleimido ethyl propionate-aminomethyl)-2,4-dihydroxy benzophenone and sebacic acid difurfuryl ester as raw material monomers; and then adding 2,2,6,6-tetramethyl-piperidine maleimide propionate as an end-capping reagent to prepare the compound type macromolecular light stabilizer, wherein the added amount of the end-capping reagent is 0.1-2% of the total weight of the raw material monomers. The invention discloses the compound type macromolecular light stabilizer based on the Diels-Alder click chemistry. The compound type macromolecular light stabilizer prepared by the preparation method disclosed by the invention has an excellent broad-spectrum ultraviolet absorption function, has a dual-light stabilizer effect of ultraviolet absorption and free radical capturing function, and has good compatibility with most high polymer materials.

Description

technical field [0001] The invention belongs to the field of polymer additives, and relates to a composite macromolecular light stabilizer based on Diels-Alder click chemistry and a preparation method thereof. Background technique [0002] With the expansion of the ozone layer hole in the earth's atmosphere, the intensity of ultraviolet radiation on the ground is continuously increasing, which has extremely adverse effects on human beings and their living environment. Long-term exposure of polymer materials to ultraviolet radiation will accelerate aging and shorten the service life of materials. In order to reduce the aging phenomenon of polymer materials caused by this ultraviolet light, adding light stabilizers to polymer materials is an effective method. [0003] Benzophenone UV absorbers are suitable for various light-colored products due to their good UV absorption performance in the range of 200-400nm, while hindered amine light stabilizers have different action modes...

Claims

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Application Information

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IPC IPC(8): C08F232/04C08F232/06C07D519/00
CPCC07D519/00C08F232/04C08F232/06
Inventor 于淑娟陆树文罗振静何婷婷
Owner 江苏多淇医疗设备有限公司
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