Low-volatility and low-mobility benzoyl formate

A free-radical and photo-initiator technology, which is used in the preparation of ester groups and hydroxyl groups, organic chemistry, etc. High efficiency, low volatility effect

Active Publication Date: 2013-10-30
INSIGHT HIGH TECH (BEIJING) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such a preparation process is obviously more complicated, which increases the cost of the material and reduces the versatility of the material
WO9833761 discloses the dibenzoyl formate of ethylene glycol, dipolyethylene glycol, and triethylene glycol as a non-volatile photoinitiator. In fact, the molecular weight of ethylene glycol dibenzoyl formate is only 326. The molecular weight of diethylene glycol dibenzoylformate is 370, which is not very ideal in terms of thermal volatility, and can still perceive a relatively obvious odor. The measured thermogravimetric analysis shows that 200 ° C loss of 10%, 250 ℃ has 20% weight loss, 50% loss at 300 ℃, due to high thermal volatility, poor performance in terms of odor and mobility; If it is too short, the water solubility of the ether chain in the structure is relatively large, and it is easy to emulsify and lose water solubility during the manufacturing process, and the manufacturing cost is high; Finally, it is also easy to be soaked and migrated by water, resulting in high mobility, so it is not an excellent and practical photoinitiator
And when the unit alkylene long chain in polyglycol dibenzoylformate structure is too long, can reduce the hardness of cured film; The content of the functional group benzoylformyloxy group is reduced, thereby reducing its initiation efficiency, and the addition amount must be increased to ensure the curing rate, resulting in high cost of use, so the practicability is not strong

Method used

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  • Low-volatility and low-mobility benzoyl formate
  • Low-volatility and low-mobility benzoyl formate
  • Low-volatility and low-mobility benzoyl formate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Dibutylene glycol dibenzoylformate

[0021] In a 500 ml four-neck flask, add 40.6 grams (0.25 moles) of dibutylene glycol, 82.5 grams (0.5 moles) of methyl benzoylformate and 4 g of sodium methoxide, heat up to 130 ° C and stir for 5 hours, while recovering Methanol. After cooling down, it was washed with water, and the water was evaporated under reduced pressure to obtain 104.5 g of a light yellow liquid product. High-pressure liquid chromatography analysis showed that the remaining content of methyl benzoylformate was 0.50%, the content of dibutylene diol dibenzoylformate was 98.5%, and the yield was 98%. Elemental analysis measured value (theoretical value), C: 67.28% (67.59%), H: 6.11% (6.14%). See Table 1 for H NMR spectrum data; see figure 1 .

[0022] Table 1-dibutylene glycol bisbenzoyl formate proton nuclear magnetic resonance spectrum data

[0023] serial number

[0024] g

Embodiment 2

[0026] In a 500 ml four-necked bottle, add 125.0 grams (0.5 moles) of polytetramethylene glycol 250 (containing 33% of dibutylene glycol, 38% of tributylene glycol, 22% of tetrabutylene glycol, and 4 6% pentabutylene glycol, 1% hexabutylene glycol), 165.0 g (1.0 mole) of methyl benzoylformate and 8 g of sodium methoxide, heated up to 130° C. and stirred for 8 hours, while recovering methanol. After cooling down, it was washed with water, and the water was evaporated under reduced pressure to obtain 251.3 g of a light yellow product. High-pressure liquid chromatography analysis showed that the remaining methyl benzoylformate content was 1.10%, the total content of all diesters was 98.15%, and the yield was 97.4%. The product liquid chromatography-mass spectrometry analysis results are shown in Table 2.

[0027] Table 2 Liquid chromatography-mass spectrometry analysis results

[0028]

Embodiment 3

[0030] Thermogravimetric Analysis

[0031] Show that methyl benzoylformate (MBF) loses 50% at 120 ℃ with U.S. AT instrument company Q5000 thermogravimetric analysis data, promptly volatilizes completely at 140 ℃; Existing 22% weight loss, lose 50% when 300 ℃; And the sample 200 ℃ of embodiment 1 only loses 2%, 250 ℃ only lose 5% weight, lose 20% when 300 ℃, illustrate that the sample of embodiment 1 has significant Improved heat resistance and very low volatility. See the data graph figure 2 .

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PUM

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Abstract

The invention provides compounds shown in structural formula I. In the formula, n represents 2-10. These compounds have extremely low volatility and mobility, and can be independently used as photoinitiators or be mixed with other photoinitiators for the photopolymerization process of unsaturated carbon-carbon double-bond compounds.

Description

technical field [0001] This application relates to low volatility and low mobility benzoyl formate, used alone as a photoinitiator or mixed with other photoinitiators to prepare photopolymerizable compositions containing unsaturated carbon-carbon double bond compounds. Background technique [0002] In patent documents such as US4038164, US4475999, EP132868A1 and GB1534320A1, benzoyl formate has been used as an independent photoinitiator in various compositions to play a role in photopolymerization. However, in the actual use of photopolymerization coatings, after people noticed the pollution problem of small molecular weight photoinitiators, the demand for photoinitiators with low volatility and low mobility increased with the expansion of the amount of coatings, such as Coatings requiring low odor and low migration are widely used in civil fields such as paper and flooring. Especially for food and drug packaging materials, there are more stringent testing standards to limit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/738C07C67/03C08F2/48
Inventor 赵文超王永林陈东阳李家齐张珏姚丽秀邵俊峰
Owner INSIGHT HIGH TECH (BEIJING) CO LTD
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