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Low-migration o-benzoyl benzoate

A technology of free radicals and compounds, applied in the field of low-mobility phthaloyl benzoate, can solve the problems of small molecular weight of photoinitiators, sources of new compounds, synthesis methods, structural characterization, property disclosure, pollution, etc.

Active Publication Date: 2011-02-23
INSIGHT HIGH TECH (BEIJING) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Benzophenone, 2-hydroxy-2-methyl-phenyl-1-propanone, methyl o-benzoylbenzoate and other photoinitiators, due to their small molecular weight, are not effective during the construction of the photocurable composition and after polymerization. Potential to migrate to contact or air to cause pollution
These three patents only generally describe the use of this type of compound. In the formulas of the examples, the compounds with m=1, 2, and 3 are listed as one of the components, but they do not describe this type of compound for the first time. Any disclosure of any information such as the source, synthesis method, structural characterization, and properties of the new compound

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Triethylene glycol bis(phthaloylbenzoate) ester

[0022] In a 500 ml four-necked flask, add 97.1 grams (0.5 moles) of tetraethylene glycol, 82.5 grams (1.0 moles) of methyl phthaloylbenzoate and 8 g of sodium methylate, and heat up to 130° C. and stir the reaction for 8 hours. Methanol is recovered at the same time. After cooling down, it was washed with water, and the water was evaporated under reduced pressure to obtain a yellow viscous substance. With ethyl acetate petroleum ether mixed solvent as eluent, the above-mentioned product is carried out column chromatography purification, obtains light yellow oily matter main distillate, through HPLC analysis, triethylene glycol bis-phthaloyl benzoate ( In structural formula 2, the compound with n=4) content was 98%, and the yield was 53%. Elemental analysis data: the measured value of C is 70.40 (theoretical value 70.81); the measured value of H is 5.82 (theoretical value 5.61). See Table 1 for H NMR spectrum data and ...

Embodiment 2

[0027] Example 2 Polyethylene glycol 200 di-phthaloylbenzoate

[0028] In a 500 ml four-necked bottle, add 100 grams (0.5 moles) of polyethylene glycol 200, 82.5 grams (1.0 moles) of methyl phthaloylbenzoate and 8 g of sodium methoxide, heat up to 130 ° C and stir the reaction for 8 hours, while Methanol is recovered. After cooling down, wash with water, and evaporate water under reduced pressure to obtain 180 grams of light yellow product polyethylene glycol 200 bis-phthaloylbenzoate (in structural formula 2, a mixture of n=4-10 compounds), with a content of 98.15%. The yield was 97.4%. The HPLC-MS analysis results are shown in Table 2.

[0029] Table 2 Liquid chromatography-mass spectrometry analysis results

[0030]

Embodiment 3

[0032] Embodiment 1, 2 product curing performance comparisons

[0033] The product prepared by Examples 1 and 2, methyl phthaloylbenzoate and benzophenone are respectively used as photoinitiators to make corresponding ultraviolet curable varnish compositions. The formulation of the composition is shown in Table 3.

[0034] table 3

[0035]

[0036] The prepared varnish composition was applied to paper with a 25 micron wire bar coater and cured at a speed of 100 m / min with a medium pressure mercury arc lamp with a power of 100 watts / cm. Record the number of lamp passes required to obtain a good surface and a thorough cure. The maximum odor is 5 grades, and the minimum is 1 grade. The results are shown in Table 4.

[0037] Evaluation results of different photoinitiators in table 4

[0038] Photoinitiator

[0039] The experimental results show that the products of Examples 1 and 2 have very little odor, are fully cured, and have a bright and non-sticky film surf...

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Abstract

The invention discloses a type of low-migration o-benzoyl benzoate compound, which is as shown by the formula 1, wherein n is from 4 to 10. The type of the compound has high photo-curing performance and very low migration, and can be singly used as a photoinitiator or other photoinitiators which are mixed together and used in the photo-curing process of unsaturated-carbon carbon double bond type compounds.

Description

technical field [0001] This application relates to low mobility o-benzoyl benzoate, which is used as a photoinitiator alone or mixed with other photoinitiators to prepare photocurable compositions containing unsaturated carbon-carbon double bond compounds. Background technique [0002] Methyl phthaloyl benzoate is a high-efficiency small molecular weight free radical solid photoinitiator, mainly used together with tertiary amine synergists for UV curing of unsaturated prepolymers (such as: acrylate), widely used In the formulation of light-curing coatings. [0003] However, in the actual use of photocurable coatings, people are increasingly concerned about the pollution caused by molecular migration of small molecular weight photoinitiators during use, and try to choose low-mobility photoinitiators within the range of optional photoinitiators. For example, in civil fields such as paper and flooring, low-odor and low-migration coatings are increasingly used, while food and p...

Claims

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Application Information

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IPC IPC(8): C07C69/76C08F2/48
Inventor 赵文超罗必奎李静闫庆金
Owner INSIGHT HIGH TECH (BEIJING) CO LTD
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