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Aromatic Ketophosphine Oxy Hybrid Compounds

A compound, phosphine oxide technology, applied in the field of aromatic ketophosphine oxide hybrid compounds, can solve the problems of rarity, no disclosure or mention of compound properties or uses, and achieve the effects of easy operation, high initiation activity, and easy preparation

Active Publication Date: 2017-05-03
SHENZHEN UV-CHEMTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] About the compound bibliographical report of phosphine oxygen group and corresponding acyl group non-direct linkage type structure is extremely rare, only finds in sporadic academic research (Kleiner, H.J.et.al.Justus Liebigs Annalen der Chemie, 1974,5,751-764 Guryanova, I.V.et.al.Zhurnal Obshchei Khimii, 1969,39,1983-1986), and these reports do not disclose or mention any properties or uses relevant to the photopolymerization process of these compounds

Method used

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  • Aromatic Ketophosphine Oxy Hybrid Compounds
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Experimental program
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preparation example Construction

[0017] The present invention discloses the preparation method of the compound of general formula (I) at the same time, these methods rely on some new reaction schemes, and as far as each unit reaction involved in the scheme is well known to those skilled in the art, it can be conveniently use.

[0018] When n takes a value of 1, the general reaction formula is as follows:

[0019]

[0020] The general formula of diketone precursor A and two molecules is YP of B (R 6 ) 2 [Y is H or Cl] carry out alkali-promoted condensation to obtain intermediate C, and the appropriate base can be inorganic hydroxide, alkali metal, alkoxy metal salt, or organic amine compound (aryl amine or alkyl amine). When Y is chlorine, H 2 The participation of O is necessary and the P atom in the generated C is directly a pentavalent phosphine oxide; when Y is hydrogen, it needs to be oxidized to obtain a pentavalent phosphine oxide unit after condensation. Suitable oxidants include hydrogen peroxide...

Embodiment 1

[0037]

[0038] At room temperature, take 2.1 grams of dibenzoyl and place it in a mixture of 30 milliliters of 1,4-dioxane and water (volume ratio 1:4), stir until completely dissolved, then slowly add 2.2 milliliters of dibenzoyl Phenylphosphonium chloride. After the dropwise addition was completed, the temperature was raised to 80° C. and stirring was continued for 2 hours (TLC tracking). After the reaction was completed, it was extracted three times with 30 ml of ethyl acetate, the organic phases were combined, concentrated by rotary evaporation and dried to obtain about 4.0 g of the target compound as a white solid, with a yield of about 96%.

[0039] H NMR spectrum 1 H NMR (CDCl 3): 7.88-7.81(m, 4H), 7.76-7.69(m, 2H), 7.49-7.24(m, 13H), 6.74(d, 1H, J=9.6Hz); C NMR 13 C NMR (CDCl 3 ): 193.9, 135.0, 134.9, 134.3, 133.3, 132.3, 132.1, 131.7, 131.6, 130.3, 128.9, 128.8, 128.5, 128.3, 128.2, 77.3ppm;

[0040] Elemental analysis (molecular formula C 26 h 21 PO 3 ): ...

Embodiment 2

[0043]

[0044] Under the protection of nitrogen, put 2.8 g of the product of Example 1 above into 50 ml of dry DMF, add 1.2 g of iodomethane and 1.9 g of silver oxide powder in sequence, heat at 50°C for 2 hours, then return to room temperature and stir overnight. The reaction solution was filtered with diatomaceous earth, poured into 200 ml of water, extracted 3 times with 150 ml of ethyl acetate, combined the organic phases, washed 2 times with saturated brine, dried over anhydrous sodium sulfate, filtered, evaporated to remove the solvent, and the residue was in The title compound (1.1 g, 37% yield) was obtained by silica gel column chromatography with hexane / ethyl acetate as eluent.

[0045] Elemental analysis (molecular formula C 27 h 23 PO 3 ):

[0046] Theoretical: Carbon, 76.04%; Hydrogen, 5.44%; Found: Carbon, 75.97%; Hydrogen, 5.39%.

[0047] HRMS high resolution mass spectrometry [molecular formula M+Na: C 27 h 23 PO 3 Na]:

[0048] Theoretical value: 44...

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Abstract

The invention discloses a phosphine oxide containing aromatic ketone compound with its structural formula as shown in (I). The structure can be independently used as a photoinitiator in the field of alkene-containing unsaturated compound system optical radiation radical polymerized new materials, and also can be used as one component of a photoinitiator for light polymerization of an alkene unsaturated compound or an alkene unsaturated compound containing a mixture.

Description

[0001] 【Technical field】 [0002] The present invention relates to some new aromatic ketone phosphine oxygen hybrid compounds and the application of the compounds as photoinitiators in radical photopolymerization process containing ethylenically unsaturated system. [0003] 【Background technique】 [0004] Some phosphono compounds are important photoinitiators, and the commercialized products include monophosphono TPO and bisphosphono BAPO. There have been some literature disclosures about the structure of this type of photoinitiator compound and its synthesis technology, such as EP0615980A2, WO2006056541A1, WO2011003772A1, CN1823077A, CN1659175A and so on. A key structural feature shared by these known compounds is that both the phosphoxy groups involved and the corresponding acyl groups are chemically directly bonded and linked together. This makes the O=P-C=O chromophore have a red-shifted absorption so that the energy of long-wave light can be effectively used, but it also ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/53C08F2/50
Inventor 陈婷王瑜
Owner SHENZHEN UV-CHEMTECH CO LTD
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