Mono/bis-methyl cinnamate photoinitiators as well as preparation method and application thereof

A technology of methyl cinnamate and group, which is applied in the preparation and application field of the mono- or di-methyl cinnamate compounds, and can solve the problems of strong mobility, low price, bad smell, etc.

Active Publication Date: 2019-12-13
HUBEI GURUN TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These two photoinitiators have excellent thermal stability, good yellowing resistance, and low price; the main disadvantages are: the benzaldehyde in the photolysis product has ...

Method used

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  • Mono/bis-methyl cinnamate photoinitiators as well as preparation method and application thereof
  • Mono/bis-methyl cinnamate photoinitiators as well as preparation method and application thereof
  • Mono/bis-methyl cinnamate photoinitiators as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0124] Example 1: Bis[4-(2-hydroxy-2-methylpropionyl)-phenyl]methane dicinnamate (compound 1)

[0125]

[0126] Put 34g (0.1mol) of bis[4-(2-hydroxy-2-methylpropionyl)-phenyl]methane into a 250ml three-necked flask, add 100ml of dichloromethane and 2.4g (0.1mol) of sodium hydride. After stirring evenly, 33.2 g (0.2 mol) of 3-phenyl-2-acryloyl chloride was added, and the reaction was stirred at room temperature for 3 h. Then, filter the reaction solution, wash the filtrate successively with dilute hydrochloric acid (5%), saturated aqueous sodium bicarbonate solution and distilled water, then dry overnight with anhydrous sodium sulfate and filter, remove the organic phase by distillation under reduced pressure, and recrystallize methanol to obtain Pale yellow crystals, 48 ​​g in total, 80% yield. The product has been 1 H-NMR spectrum confirmed the title compound.

[0127] 1 H-NMR (spectrum) (measured in Acetone-d6) (δppm): 1.60 (s, 12H), 3.96 (s, 2H), 6.31 (d, 2H), 6.78 (...

Embodiment 2

[0128] Example 2: 2-hydroxy-1-(4-(4-(1-hydroxycyclohexanecarbonyl)phenoxy)phenyl)-2-methyl-1-propanone monocinnamate (compound 2)

[0129]

[0130] Put 38.2g (0.1mol) of 2-hydroxy-1-(4-(4-(1-hydroxycyclohexanecarbonyl)phenoxy)phenyl)-2-methyl-1-propanone in a 250ml three-necked flask , 100 ml of dichloromethane and 10.1 g (0.1 mol) of triethylamine were added. After stirring evenly, 16.6 g (0.1 mol) of 3-phenyl-2-acryloyl chloride was added, and the reaction was stirred at room temperature for 3 h. Then, filter the reaction solution, wash the filtrate successively with dilute hydrochloric acid (5%), saturated aqueous sodium bicarbonate solution and distilled water, then dry overnight with anhydrous sodium sulfate and filter, remove the organic phase by distillation under reduced pressure, and recrystallize methanol to obtain Pale yellow crystals, 38 g in total, yield: 74.2%. The product has been 1 H-NMR spectrum confirmed the title compound.

[0131] 1 H-NMR (spectrum)...

Embodiment 3

[0132] Example 3: Bis[4-(2-hydroxy-2-methylpropionyl)phenyl]sulfide monocinnamate (compound 3)

[0133]

[0134] Put 35.8g (0.1mol) of bis[4-(2-hydroxy-2-methylpropionyl)phenyl]sulfide in a 250ml three-necked flask, add 100ml of dichloromethane and 2.4g (0.1mol) of sodium hydride. After stirring evenly, 16.6 g (0.1 mol) of cinnamoyl chloride was added, and the reaction was stirred at room temperature for 3 h. Then, filter the reaction solution, wash the filtrate successively with dilute hydrochloric acid (5%), saturated aqueous sodium bicarbonate solution and distilled water, then dry overnight with anhydrous sodium sulfate and filter, remove the organic phase by distillation under reduced pressure, and recrystallize methanol to obtain Pale yellow crystals, 36 g in total, yield: 73.7%. The product has been 1 H-NMR spectrum confirmed the title compound.

[0135] 1 H-NMR (spectrum) (measured in Acetone-d6): 1.78 (s, 6H), 2.34 (s, 6H), 6.54 (d, 1H), 7.35 (m, 13H), 8.11 (d,...

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Abstract

The invention relates to methyl cinnamate compounds in a formula (I), wherein each variable in the compounds in the formula (I) is defined in the description. The invention further relates to a methodfor preparing the methyl cinnamate compounds, including an esterification reaction of a compound in a formula (II) and a compound in a formula (III). The methyl cinnamate compounds can be used as photoinitiators, can absorb radiant heat in the range of 200-400 nm and have good stability and yellowing resistance; and more importantly, the initiators greatly solve the problems of foreign odors andhigh migration as compared with existing alpha-hydroxyketone photoinitiator, besides, the photoinitiators have ultraviolet (UV) absorption red shift to about 300-400 nm and are applicable to UV-LED light source curing. The invention also relates to application of mono/bis-methyl cinnamate compounds as photoinitiators.

Description

technical field [0001] The invention relates to mono- or bis-cinnamic acid methyl ester compounds, which can be used as photoinitiators, and also relates to the preparation and application of the mono- or bis-cinnamic acid methyl ester compounds. Background technique [0002] Photoinitiator, also known as photosensitizer or photocuring agent, is a kind of energy that can absorb a certain wavelength in the ultraviolet region (250-400nm) or visible region (400-600nm), and generate free radicals, cations, etc., thereby initiating monomer Polymerization crosslinks cured compounds. In the photocuring system, the photoinitiator generally accounts for 3-5%. Although the content is low, it is the key component and plays a decisive role in the photocuring speed. It is related to whether the oligomer and diluent can be quickly cross-linked and solidified when the formulation system is irradiated with light, thereby changing from liquid to solid. At present, photocuring technology ha...

Claims

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Application Information

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IPC IPC(8): C07C69/618C07C69/734C07C67/14C07C323/22C07C323/62C07C225/22C07C319/20C07C221/00G03F7/004C08F2/48
CPCC07C69/618C07C69/734C07C323/22C07C323/62C07C225/22G03F7/004C08F2/48C07C2601/14C07C2602/08
Inventor 邹应全庞玉莲樊书珩
Owner HUBEI GURUN TECH CO LTD
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