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Polymerizable II-type photoinitiator and preparation method thereof

A technology for polymerizing photoinitiators and compounds, which is applied in the field of polymerizable type II photoinitiators and their preparation, can solve the problems of toxicity and deterioration of physical properties of packaging materials, and achieve low mobility, excellent photocuring performance, and high activity. Effect

Active Publication Date: 2019-05-10
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Migration is the process of direct transfer of compounds between the cured layer and the packaging substrate. This migration may cause deterioration of the physical properties of the packaging material, but more importantly, the compounds can also migrate further into the food. Many compounds themselves are not very toxic or not toxic, but becomes toxic when used in large quantities

Method used

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  • Polymerizable II-type photoinitiator and preparation method thereof
  • Polymerizable II-type photoinitiator and preparation method thereof
  • Polymerizable II-type photoinitiator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of Compound A

[0032] Add 48.8g of pentaerythritol diacrylate (0.2mol), 23.3g of triethylamine (0.21mol) and 240ml of dichloromethane into the three-necked flask, and react with electromagnetic stirring. A constant pressure dropping funnel with 46.3g of chloroacetyl chloride (0.41mol) and 120ml of dichloromethane is slowly added dropwise at low temperature, and the temperature is kept between 0 and -5°C. After the dropwise addition is completed, move to room temperature for reaction. TLC monitored the completion of the reaction. Filter triethylamine hydrochloride, wash with saturated sodium bicarbonate 2-3 times, then wash with saturated brine, dry over anhydrous magnesium sulfate, and spin dry. Separation and purification by chromatographic column to obtain a transparent oily substance with a yield of about 85% and a purity of ≥95%. 1 H NMR (400MHz, CDCl 3 )δ6.45(dd,1H), 6.05(m,2H), 5.58(dd,2H), 4.34(s,4H), 4.10(s,4H), 4.00(s,4H).

[0033]...

Embodiment 2

[0034] Example 2: Preparation of Compound B

[0035] Add 48.8g of pentaerythritol di(acrylic acid) ester (0.2mol), 23.3g of triethylamine (0.21mol) and 240ml of dichloromethane into the three-necked flask, and react with electromagnetic stirring. The three ports of the three-necked flask are respectively connected to a thermometer and a drying tube and a constant pressure dropping funnel containing 51.6g 2-chloropropionyl chloride (0.41mol) and 120ml dichloromethane, slowly add dropwise at low temperature, the temperature is maintained between 0 and -5°C, after the dropwise addition is completed, move to React at room temperature. TLC monitored the completion of the reaction. Filter triethylamine hydrochloride, wash with saturated sodium bicarbonate 2-3 times, then wash with saturated brine, dry over anhydrous magnesium sulfate, and spin dry. Separation and purification by chromatographic column to obtain a transparent oily product with a yield of about 80% and a purity of...

Embodiment 3

[0037] Example 3: preparation of

[0038]In a 500ml four-neck flask equipped with mechanical stirring, add 50.0g thioxanthone-4-carboxylic acid, 250ml tetrahydrofuran, 23.6g triethylamine, 25.6g methyl chloroacetate, and heat to 50-60°C for 8 hours. After suction filtration, the filtrate was cooled to 0-5° C., stirred and crystallized for 2 hours, and the crude product was obtained by suction filtration. The crude product was recrystallized with toluene, and after drying, 53.7 g of yellow flaky crystals were obtained. The yield was 84%, and the content was ≥98.0%.

[0039] In a 500ml four-necked bottle equipped with a mechanical stirrer and a water separator, add 32.8g thioxanthone-4-formyloxyacetic acid methyl ester, 0.3g sodium methoxide, 200ml methylcyclohexane, 13.5g pentaerythritol diacrylic acid Esters, 0.2g p-hydroxyanisole, heated to reflux to separate methanol for 14 hours. The temperature was lowered slowly, the solid was precipitated, and filtered to obtain 24.2 ...

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Abstract

The invention discloses a polymerizable photoinitiator and a preparation method thereof. A formula of the photoinitiator is as shown in the specification. The photoinitiator has advantages that compatibility of the photoinitiator to photopolymerization systems is improved, photoinitiator residual in a photocuring process is sharply reduced, and the photoinitiator can further serve as a monomer forsynthesis of macromolecular photoinitiators. Therefore, the photoinitiator has a promising application prospect in the field of photocuring.

Description

Technical field: [0001] The invention relates to a novel polymerizable type II photoinitiator and a preparation method thereof. Background technique: [0002] UV curing technology is an environmentally friendly green technology in the fields of coatings, inks, adhesives, etc. Compared with traditional solvent-containing systems, UV curing technology has outstanding features such as no solvent emission, high efficiency, and energy saving. The main body of the material is generally composed of oligomers, monomers and photoinitiators, which are fully cured under the action of sufficient ultraviolet light. With the application of UV light curing materials more and more widely, some unexpected problems have appeared, and the initiator itself The free radicals of free radicals have no or low initiation activity, and remain in the cured film after quenching. The toxicity caused by the migration and precipitation of residual initiators to the surface has become a potential major hid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/16C08F2/48
Inventor 刘新月姚娜董月国武瑞张齐
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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