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Piperazino photoinitiation sensitiser

A compound and group technology, applied in the field of piperazine sensitizers, can solve problems such as unfavorable hydrogen abstraction and Michler's ketone not being particularly effective

Inactive Publication Date: 2011-11-23
SUN CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although it can function as a photoinitiator by itself, Michler's ketone is not particularly effective due to the remarkable charge transfer properties to its lowest triplet state
This makes hydrogen abstraction from the donor molecule unfavorable due to the high electron density on the carbonyl oxygen

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Preparation of 4,4'-dipiperazinylbenzophenone

[0072]

[0073] 5.0 g of 4,4'-difluorobenzophenone (0.0229 mol), 3.94 g of piperazine (0.0458 mol), 6.60 g of potassium carbonate powder (0.0478 mol) and 50 ml of anhydrous DMSO (dimethyl sulfone) were mixed in a three-necked flask equipped with stirrer, nitrogen inlet, condenser, calcium chloride drying tube / nitrogen outlet and temperature sensor. The mixture was heated to reflux under a constant flow of nitrogen for 12 hours (-190 °C). The mixture was then cooled to room temperature and filtered to remove inorganics. The reaction flask was rinsed with an additional 75ml DMSO. The DMSO solution was then added to 100 g of water. The resulting mixture was extracted with dichloromethane (3x75ml). The dichloromethane layers were combined and washed with 100 ml of saturated sodium chloride solution. The dichloromethane layer was then dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, ...

Embodiment 2

[0079]

[0080]2.84 g of propoxylated neopentyl glycol diacrylate (PNPGDA, molecular weight 328) (0.00866 mol), 2.00 g of the product of Example 1 (4,4'-dipiperazinylbenzophenone) (0.00571 mol), toluene 30ml and 0.115g of 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) (catalyst) in a two-neck round bottom equipped with stirrer, condenser and temperature sensor Mix in the flask. The mixture was heated to reflux for a total of 10 hours (over 2 days). The mixture was then cooled and filtered to remove unreacted 4,4'-dipiperazinylbenzophenone, then the solvent was removed on a rotary evaporator to give the product.

[0081] The yield of the product was 4.95 g as a viscous slightly yellow liquid.

[0082] The product was analyzed by GPC.

[0083] GPC: Mn 5167, Mw 11664.

Embodiment 3

[0085]

[0086] 2.60g tripropylene glycol diacrylate (TPGDA, molecular weight 300) (0.00866 mol), the product (4,4'-dipiperazinyl benzophenone) (0.00433 mol) of embodiment 1 of 1.515g, toluene 30ml and 0.115 g of 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) (catalyst) were mixed in a two necked round bottom flask equipped with stirrer, condenser and temperature sensor. The mixture was heated to reflux for a total of 10 hours (over 2 days). The mixture was then cooled and filtered to remove unreacted 4,4'-dipiperazinylbenzophenone, then the solvent was removed on a rotary evaporator to give the product.

[0087] Product yield 3.77 g (91.6%) as a viscous yellowish liquid.

[0088] The product was analyzed by GPC.

[0089] GPC: Mn 3165, Mw 3885.

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Abstract

The present invention relates to a piperazino photoinitiation sensitizer. Compounds of formula (I) [in which: A and B are terminal groups; R<1> represents a group of formula (II) or (III); R<2> is alkyl or aryl; Z is a group -(CHR<3>)n , where R<3> is hydrogen, hydroxy or alkyl, and n is a number from 0 to 6; Y is carbonyl or a group -CH2-; Q represents a residue of a dihydroxy compound; and x is a number from 1 to 100] are useful sensitisers for use with Type II photoinitiators in the formulation of printing inks and other energy curable coatings.

Description

[0001] This application is a divisional application of the international application PCT / US2005 / 003505, which entered the Chinese national phase on July 28, 2006, with the application number 200580003572.4 and the invention name "piperazine sensitizer". technical field [0002] The present invention relates to a new series of piperazine sensitizers for radiation curing, for example in the radiation curing of coating compositions such as printing inks or varnishes. Background technique [0003] Photocurable compositions are cured by exposure to radiation, usually ultraviolet radiation, and include, for example, lacquers which may be applied to wood, metal or similar substrates by suitable techniques such as roller coating or curtain coating. They may also be formulated as inks, for example applied by various techniques such as letterpress printing, offset printing, rotographic printing, screen printing, flexographic printing or inkjet printing. Depending on the specific print...

Claims

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Application Information

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IPC IPC(8): C07D295/112C07D295/15C08F2/50G03F7/031
CPCG03F7/031C07D295/112C07D295/15C07D401/10C07D401/14
Inventor 肖恩·劳伦斯·赫利希布赖恩·罗瓦特
Owner SUN CHEM CORP