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(Methyl) acrylate oxazole heterocycle borate, and preparation and application thereof

A technology of methacrylate and heterocyclic boronic ester, which is applied in the field of (meth)acrylated azacyclic boronic ester and its preparation, and can solve migration loss, lack of long carbon chain balance performance, boric acid ester Does not have free radical polymerizable properties and other issues

Inactive Publication Date: 2011-10-26
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

What's more, directly using amino alcohol to form borate ester, the color is extremely dark, lacks the necessary long carbon chain balance performance, and in addition to good stability against hydrolysis, other application performance is generally poor
[0006] Based on the currently known design and synthesis technologies of various borate esters, except for the synthesis of borate esters using N-methylolacrylamide, other reported borate esters do not have free radical polymerizable properties and are only used as a function Sexual free components are added to formula products, during the process of material processing and use, there may be migration loss
There are no research reports on acrylated borates, and the technology of obtaining borates through Michael addition, and the research on photocured borates have not been mentioned.

Method used

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  • (Methyl) acrylate oxazole heterocycle borate, and preparation and application thereof
  • (Methyl) acrylate oxazole heterocycle borate, and preparation and application thereof
  • (Methyl) acrylate oxazole heterocycle borate, and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] Add 113.0 g (0.5 mol) of 1,6-hexanediol diacrylate into a three-necked flask, install a condenser tube, an addition funnel, and a mechanical stirrer, and place the flask in a cold water bath environment. Add 38.0 g (0.36 mol) diethanolamine dropwise under rapid stirring. After the dropwise addition of diethanolamine, continue to stir in a cold water bath environment for 6 hours, during which time samples are taken for NMR testing. It is confirmed that the acrylate in the system is 5.5~6.3 The relative intensity of the NMR signal peaks in the ppm interval no longer decreases, and the Michael addition reaction between the diethanolamine and the acrylate double bond is complete. Add 50 ml of toluene, 11.0 g (0.178 mol) of boric acid and 0.1 g of phenothiazine, replace the oil bath heating device, install a water separator, stir and heat to 95 °C, wait for the reflux to separate the water, and after the water separation begins, lower the temperature appropriately. Continue ...

Embodiment 2

[0111] Take 151.0 g (0.5 mol) of tripropylene glycol diacrylate and add it to a three-necked flask, install a condenser tube, an addition funnel, and a mechanical stirrer, and place the flask in a cold water bath environment. Add 31.5 g (0.3 mol) diethanolamine dropwise under rapid stirring. After the dropwise addition of diethanolamine, continue to stir in a cold water bath for 6 hours, during which time samples are taken for NMR testing. It is determined that the acrylate in the system is 5.5~6.3 The relative intensity of the NMR signal peaks in the ppm interval no longer decreases, and the Michael addition reaction between the diethanolamine and the acrylate double bond is complete. Add 70 ml of toluene, 9.2 g (0.15 mol) of boric acid and 0.1 g of phenothiazine, replace the oil bath heating device, install a water separator, stir and heat to 95 °C, wait for the reflux to separate the water, and after the water separation begins, lower the temperature appropriately. Continue...

Embodiment 3

[0113] Add 234.0 g (0.5 mol) of ethoxylated bisphenol A diacrylate SR 349 ​​(Sartomer, molecular weight 468) into a three-neck flask, install a condenser tube, an addition funnel, and a mechanical stirrer, and place the flask in a cold water bath environment middle. Add 21.0 g (0.2 mol) diethanolamine dropwise under rapid stirring. After the dropwise addition of diethanolamine, continue to stir in a cold water bath environment for 6 hours, during which time samples are taken for NMR testing. It is confirmed that the acrylate in the system is 5.5~6.3 The relative intensity of the NMR signal peaks in the ppm interval no longer decreases, and the Michael addition reaction between the diethanolamine and the acrylate double bond is complete. Add 100 ml of toluene, 6.2 g (0.1 mol) of boric acid and 0.15 g of phenothiazine, replace the oil bath heating device, install a water separator, stir and heat to 95 °C, wait for the reflux to separate the water, and after the water separation ...

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Abstract

The invention discloses a (methyl) acrylate oxazole heterocycle borate compound, which is annular borate containing (methyl) acrylate group and tertiary amine composition. The invention also discloses a preparation method of the compound. The method comprises the steps that: bi-functional (methyl) acrylate compound or tri-functional (methyl) acrylate compound is subject to a reaction with N,N-bi(hydroxyalkyl)secondary amine; through a Michael addition reaction upon acrylate group, (methyl) acrylate with N,N-bi(hydroxyalkyl)amid is obtained; Under the coexistence of a desiccant and a polymerization inhibitor, (methyl) acrylate with N,N-bi(hydroxyalkyl)amid is subject to a condensation reaction with boric acid, such that (methyl) acrylate azacyclo-borate is obtained. The (methyl) acrylate oxazole heterocycle borate prepared by the present invention can be applied to the fields of light-cured paint, printing ink or adhesive, and has good anti-hydrolytic stability, adhesive performance, wear resistance and antistatic performance.

Description

technical field [0001] The invention relates to coatings, inks and adhesives in the technical field of polymer materials, in particular to a (meth)acrylated azacyclic borate and its preparation method and application. Background technique [0002] Light-curing coatings are green, energy-saving, environmentally friendly, and high-efficiency coatings that were first industrialized by Bayer in Germany in the 1960s. Their formula does not contain organic solvents. The high-performance coating products of combined curing have been widely used in the coating of wood, plastic, metal, stone and other substrates, and have formed a large-scale market in many fields such as building materials, furniture, packaging, home appliances, communication equipment, flat panel displays, and automobiles. , and derived from the formation of high value-added light-curable ink and light-curable adhesive industry. [0003] The light-curing formula is generally composed of light-curing resin, acrylat...

Claims

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Application Information

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IPC IPC(8): C07F5/04C09D4/02C09D11/02C09J4/02C09D11/00
Inventor 庞来兴杨建文祝方明
Owner SUN YAT SEN UNIV
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