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Soluble oxime ester and aromatic ketone photo polymerization initiator

A technology of definition and substituent, applied in the field of soluble oxime ester and aromatic ketone photopolymerization initiators, can solve the problems of practical application limitation, insufficient solubility, difficult to dissolve and so on

Active Publication Date: 2013-06-05
荆门市美邦化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the basis of this structure, when patents CN101528694A, CN101855201A, CN101528682A, WO2008078678A1, CN102086171A etc. replaced the acyl substituent on the carbazole ring with a nitro group, they found that the photosensitivity was significantly improved. However, these nitrocarbazole compounds are used in commonly used resin systems. It is extremely difficult to dissolve or have insufficient solubility in medium, and cannot be compatible with solvents, monomers, oligomers, and various pigments and other additives, so it cannot be effectively compounded under actual application conditions, so the potential practical application is greatly limited

Method used

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  • Soluble oxime ester and aromatic ketone photo polymerization initiator
  • Soluble oxime ester and aromatic ketone photo polymerization initiator
  • Soluble oxime ester and aromatic ketone photo polymerization initiator

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089]

[0090] Step 1: Place 2.4 g of NaOH in 50 ml of dry DMF under an ice-water bath, stir for 10 minutes, then add 5 g of carbazole in batches and continue stirring for half an hour, then add 2.7 ml of bromoethane dropwise. After the dropwise addition, the ice-water bath was removed and stirring was continued at room temperature for 5-8 hours (TLC tracking). After the reaction was completed, the reaction solution was slowly poured into an ice-water bath, extracted 4 times with 100 ml of ethyl acetate each time, the extract was collected, dried over sodium sulfate, and concentrated by rotary evaporation to obtain a crude product. Dissolve it in an appropriate amount of dichloromethane (until it dissolves), spread 5 cm thick silica gel in the Buchner funnel, filter, and wash the silica gel layer 3 times with dichloromethane (20 ml each time) (TLC detection) , the mother liquor was collected, concentrated by rotary evaporation and dried to obtain 5.6 g of N-ethylcarbazole ...

Embodiment 2

[0115]

[0116] With reference to the reaction conditions in the first to fifth steps of Example 1, only benzoyl chloride was used to replace the acetyl chloride in Example 1 in the final esterification step of the fifth step, and the light yellow target product was obtained with a yield of 92%.

[0117] Target product NMR data:

[0118] 1 H-NMR (CDCl 3 , 400MHz): 8.90(s, 1H), 8.48(s, 1H), 8.37(dd, 1H, J=9.2Hz, J=2Hz), 7.92(dd, 1H), 7.77(m, 3H), 7.78( m, 3H), 7.69-7.26 (m, 16H), 4.39 (q, 2H, J=7.2Hz), 1.47ppm (t, 3H, J=7.2Hz);

[0119] 13 C-NMR (CDCl 3 , 100MHz): 163.9, 163.8, 143.4, 142.3, 141.1, 136.1, 133.7, 133.6, 132.7, 132.2, 132.1, 132.0, 131.9, 131.8, 131.7, 131.6, 131.5, 130.5, 130.5, 129.9, 129.9 7 ppm.

Embodiment 3

[0121]

[0122] The first step: the same as the first step in embodiment one;

[0123] The second step: similar to the second step of Example 1, the only difference is that the acylation reagent is changed to CH 3 C(O)C(O)Cl, the product was a pale yellow solid.

[0124] NMR data:

[0125] 1 H-NMR (CDCl 3 , 400MHz): 8.82(s, 1H), 8.20-8.17(m, 2H), 7.58-7.55(dd, 1H), 7.49-7.46(m, 2H), 7.35(dd, 1H), 4.42(q, 2H , J=7.2Hz), 2.62(s, 3H), 1.49ppm(t, 3H, J=7.2Hz);

[0126] 13 C-NMR (CDCl 3 , 100MHz): 202.0, 191.4, 143.6, 140.7, 128.0, 126.8, 126.5, 124.5, 123.2, 123.1, 122.8, 120.9, 120.5, 109.2, 108.7, 37.9, 26.8, 13.8ppm.

[0127] The third to fifth steps: the same as the third to fifth steps of Example 1; 2.7 g of the light yellow target compound was prepared with a yield of 83%.

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Abstract

The invention relates to the technical field of optical radiation free radical polymerization novel materials, in particular to a novel compound of oxime ester and an aromatic ketone photo polymerization initiator, wherein the structural formula of the novel compound is shown as (I). The compound has excellent and practical dissolution performance and high light sensitivity, can be used as a photo initiator independently in the filed of the optical radiation free radical polymerization novel materials in an olefin-containing unsaturated compound system, and can also be used as one of the photo initiators in the photo polymerization of an olefinic unsaturated compound mixture or an olefin-containing unsaturated compound mixture.

Description

【Technical field】 [0001] The present invention relates to the technical field of new materials for free radical polymerization of light radiation, in particular to a class of new oxime ester and aromatic ketone photoinitiator compounds represented by general structural formula (I), which have both excellent and practical solubility properties And high photosensitivity, it can be used alone as a photoinitiator in the field of new materials for photoradiation free radical polymerization containing ethylenically unsaturated compounds, and can also be used as a light source for photopolymerization of ethylenically unsaturated compounds or mixtures of ethylenically unsaturated compounds. One of the starter components. 【Background technique】 [0002] Light (ultraviolet light or visible light or equivalent light source) radiation curing (UV Curing) containing ethylenically unsaturated systems is a key technology in the field of new materials, and one of its prominent and widespread...

Claims

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Application Information

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IPC IPC(8): C07F9/572C07F9/53C07F9/6553C07F9/6558C07F9/6561C07D209/88C07D209/86C07C323/47C07D333/76C07D307/91C07D345/00C07C251/66C07C391/02C07D335/16C07C323/32C08F2/48C08F2/54G03F7/004G03F7/027
Inventor 王智刚赵新阳宋怀海
Owner 荆门市美邦化学有限公司
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