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Beta-diketone cerium (IV) compound, preparation and application thereof

A compound, C1-C6 technology, applied in the field of preparation and its application as a photoinitiator

Pending Publication Date: 2020-06-19
HUBEI GURUN TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, photoinitiators based on organic cerium compounds have not been reported

Method used

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  • Beta-diketone cerium (IV) compound, preparation and application thereof
  • Beta-diketone cerium (IV) compound, preparation and application thereof
  • Beta-diketone cerium (IV) compound, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] Embodiment 1: the preparation of compound 1

[0112]

[0113] The synthetic route of compound 1 is as follows:

[0114]

[0115] In a 100mL three-necked flask, the CeCl 3 ·7H 2 O (1.86 g, 5 mmol) was dissolved in 10 mL of ethanol. Acetylacetone (2.50 g, 25 mmol) was dissolved in 10 mL of ethanol in advance, and then added to the solution in the above-mentioned three-necked flask to obtain a pale yellow transparent reaction solution. After stirring for 10 minutes, 12.5 mL of 2M dilute ammonia water was added dropwise, and the reaction solution gradually turned orange and then reddish brown. The reaction was stirred at room temperature for 2 h, and most of the solvent was vacuum distilled out of the system after the reaction. A red-brown solid was obtained by filtration, washed with 10 mL of ethanol, and the washing was repeated twice, and vacuum-dried for 12 hours to obtain a red-brown powder with a yield of 2.23 g and a yield of 83.1%, which was identified as ...

Embodiment 2

[0117] Embodiment 2: the preparation of compound 12

[0118]

[0119] The synthetic route of compound 12 is as follows:

[0120]

[0121] In a 100mL three-necked flask, the CeCl 3 ·7H 2 O (1.86 g, 5 mmol) was dissolved in 10 mL of ethanol. Benzoylacetone (3.5 g, 22.5 mmol) was dissolved in 10 mL of ethanol in advance, and then added to the solution in the above-mentioned three-necked flask to obtain a pale yellow transparent reaction solution. After stirring for 10 min, 3.5 mL of triethylamine (25.2 mmol) was added dropwise, and the reaction solution gradually turned orange and then reddish brown. Stir the reaction at room temperature for 2h, then filter, and the filter residue is a reddish-brown solid. The obtained solid was washed with 5 mL of ethanol and dried in vacuo for 12 h to obtain a reddish-brown solid with a yield of 1.84 g and a yield of 46.9%, which was identified as compound 12.

[0122] 1 H NMR (400MHz, DMSO) δ7.88 (d, J = 6.8Hz, 8H), 7.58–7.19 (m, 1...

Embodiment 3

[0123] Embodiment 3: the preparation of compound 18

[0124]

[0125] The synthetic route of compound 18 is as follows:

[0126]

[0127] In a 100mL three-necked flask, Ce(NO 3 ) 3 ·6H 2 O (0.43 g, 1 mmol) was dissolved in 5 mL of absolute ethanol. Dibenzoylmethane (0.90 g, 4 mmol) was dissolved in 10 mL of absolute ethanol in advance, and then added to the solution in the above-mentioned three-necked flask to obtain a pale yellow transparent reaction solution. After stirring for 10 min, 4 mL of 1M dilute ammonia water was added dropwise, and the reaction solution turned reddish brown. Stir the reaction at room temperature for 2h, then filter, and the filter residue is a reddish-brown solid. The obtained solid was washed with 5 mL of absolute ethanol, and dried in vacuum for 12 h to obtain a reddish-brown solid with a yield of 0.99 g and a yield of 95.8%, which was identified as compound 18.

[0128] 1 H NMR (400MHz, CDCl 3 )δ8.04–7.99 (m,16H), 7.46–7.28 (m,24H),...

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PUM

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Abstract

The present invention relates to beta-diketone cerium (IV) compound represented by a formula (I), wherein R1, R2 and R3 are defined in the specification, and the compound is wide in absorption band, is suitable for curing in a near ultraviolet-visible light region as a photoinitiator, and has the advantages of high sensitivity, low toxicity, low cost, easiness in obtaining and the like. The invention also relates to preparation and use of the compound represented by the formula (I). The compound represented by the formula (I) is particularly suitable as photoinitiator in a UV-LED photocuring system, specifically in a photocuring system having a radiation wavelength of 300 to 600 nm.

Description

technical field [0001] The invention relates to β-diketone cerium (IV) compounds, which can be used as photoinitiators, the preparation of the compounds and their application as photoinitiators. Background technique [0002] Photocuring refers to the process in which a polymerizable liquid monomer (or soft film) is transformed into a solid material (or solid film) under light radiation conditions. Compared with traditional thermal curing, light curing has the advantages of high curing efficiency, low energy consumption, and less pollution, and is an environmentally friendly technology. In recent years, photocuring technology has been widely and rapidly developed, and it is widely used in many traditional and high-tech fields, such as radiation curing, laser imaging, microlithography, microelectronics, nanotechnology and so on. [0003] The common photocuring system mainly includes three parts: photoinitiating system, polymerizable medium and light source. The three are int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/92C07C255/17C07C205/45C07C309/44C07C59/185C07C69/716C07D303/32C07C309/07C07D213/50C07D307/46C07D333/22C07C225/06C07C45/77C07C253/30C07C201/12C07C303/22C07C51/347C07C67/00C07C221/00C08F122/20C08F2/48C08F2/50
CPCC07C49/92C07C255/17C07C205/45C07C309/44C07C59/185C07C69/716C07D303/32C07C309/07C07D213/50C07D307/46C07D333/22C07C225/06C07C45/77C07C253/30C07C201/12C07C303/22C07C51/347C07C67/00C07C221/00C08F122/20C08F2/48C08F2/50C07C2601/02C07C2601/04C07C2601/08C07C2601/14
Inventor 邹应全高明庞玉莲
Owner HUBEI GURUN TECH CO LTD
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