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Compound, active energy ray curable composition, cured article thereof, printing ink, and inkjet recording ink

A compound and reactive compound technology, applied in printing, ink, application, etc., can solve problems such as poor photoinitiation ability and poor curing, and achieve the effect of fast curing speed

Inactive Publication Date: 2017-02-15
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the photoinitiator disclosed in Patent Document 3 is slightly inferior in photoinitiation ability, and problems such as poor curing occur particularly in applications that require a curing speed of ultraviolet curable inks and the like.

Method used

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  • Compound, active energy ray curable composition, cured article thereof, printing ink, and inkjet recording ink
  • Compound, active energy ray curable composition, cured article thereof, printing ink, and inkjet recording ink
  • Compound, active energy ray curable composition, cured article thereof, printing ink, and inkjet recording ink

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0294] (Example 1) Synthesis of compound (5') [2-dimethylamino-1-(4-morpholinophenyl)-2-(4-carboxybenzyl) butane-1-one]

[0295] [Process 1]

[0296]

[0297] 121.8 g of aluminum chloride (anhydrous) and 300 mL of dehydrated dichloromethane were charged into a 1 L four-necked flask equipped with a stirrer, a thermometer, a nitrogen gas introduction tube, an alkali trap (Alkali Trapp) and a dropping funnel, under a nitrogen stream , using an ice bath for ice cooling. 200 g of 2-bromobutyryl bromide was added thereto. A mixed solution of 83.6 g of fluorobenzene and 100 mL of dehydrated dichloromethane was dropped into the previous flask over 20 minutes using a dropping funnel. After the dropwise addition was completed, the ice bath was removed, and stirring was continued for 2 hours as it was.

[0298] After the stirring was completed, the reaction solution was poured into 1 L of ice water, and the stirring was continued for 2 hours. After standing still, the liquid was s...

Embodiment 2

[0316] (Example 2) Compound (6') (2-Dimethylamino-1-(4-morpholinophenyl)-2-(4-(1-hydroxyl-1-oxopropane-2-yl) Synthesis of benzyl)butan-1-one)

[0317]

[0318] In step 1 of Example 1, 97.6 g of methyl 2-(4-bromomethyl)phenylpropionate (105) was used instead of 87.0 g of methyl 4-(bromomethyl)benzoate (103), except Otherwise, react according to the method described in Example 1 to synthesize compound (6') (2-dimethylamino-1-(4-morpholinophenyl)-2-(4-(1-hydroxyl-1 -Oxopropan-2-yl)benzyl)butan-1-one).

[0319] 1 H-NMR (CDCl 3 ): 0.66ppm (t, 3H, - CH 3 ), 1.46(d, 3H, CH- CH 3 ), 1.83ppm (m, 1H, - CH 2 -), 2.00ppm (m, 1H, - CH 2 -), 2.35(s, 6H, N- CH 3 ), 3.16(s, 2H, - CH 2 -Ph), 3.30ppm (m, 4H, morpholine), 3.67 (q, 1H, CH -CH 3 ), 3.84ppm (m, 4H, morpholine), 6.82ppm (d, 2H, aromatic), 7.39ppm (d, 2H, aromatic), 7.95ppm (d, 2H, aromatic), 8.35ppm (d , 2H, aromatic)

Embodiment 3

[0320] (Example 3) Compound (8') [2-methyldodecylamino-1-(4-morpholinophenyl)-2-(4-carboxybenzyl)butan-1-one] synthesis

[0321]

[0322] In step 1 of Example 1, 256.6 g of methyl dodecylamine was used instead of 789.9 g of 11% dimethylamine / ethanol solution, except that, according to the method described in Example 1, compound (8') was synthesized ( 2-methyldodecylamino-1-(4-morpholinophenyl)-2-(4-carboxybenzyl)butan-1-one).

[0323] 1 H-NMR (CDCl 3 ): 0.66ppm (t, 3H, - CH 3 ), 0.84ppm (t, 3H, - CH 3 ), 1.20ppm (m, 18H, - CH 2 -), 1.34ppm (m, 2H, N-CH 2 - CH 2 -CH 2 -), 1.83ppm (m, 1H, - CH 2 -), 2.00ppm (m, 1H, - CH 2 -), 2.30(s, 3H, N- CH 3 ), 2.40(m, 1H, N- CH 2 -), 2.60 (m, 1H, N- CH 2 -), 3.10(s, 2H, - CH 2-Ph), 3.30ppm (m, 4H, morpholine), 3.84ppm (m, 4H, morpholine), 6.82ppm (d, 2H, aromatic), 7.39ppm (d, 2H, aromatic), 7.95ppm (d, 2H, aromatic), 8.35ppm (d, 2H, aromatic)

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Abstract

The present invention improves curability and reduces post-curing migration in a photopolymerization initiator. As a photopolymerization initiator, the present invention uses a compound obtained as a result of a Michael addition reaction between an alpha-aminoacetophenone skeleton-containing compound (I) represented by general formula (1), and a reactive compound (II) which functions as a Michael acceptor. (In formula (1), R1 represents an aliphatic group or the like, R2-R3 each independently represent an aliphatic group or the like, R4-R7 each independently represent a hydrogen atom or the like, X1 represents a single bond or a C1-6 alkylene group, X2 represents a carbonyl group or the like, and Y1 and Y2 represent a group represented by general formula (2) or the like. Meanwhile, when Y1 and Y2 both have a structure represented by general formula (2), the X5 in one or both is -NH-.) (In general formula (2), X3 and X4 each independently represent a C2-6 straight-chain or branched alkylene group or the like, and X5 represents a single bond, -O-, or -NH-).

Description

technical field [0001] The present invention relates to a compound having a group having a Michael addition donating function, a compound useful as an intermediate therefor, a photopolymerization initiator comprising the compound having a group having a Michael addition donating function, and a photopolymerization initiator containing the group The active energy ray curable composition of an initiator. Background technique [0002] Conventionally, active energy ray curing systems have been widely used from the viewpoint of high productivity, cost reduction of curing energy, and VOC reduction. In particular, compared with other active energy ray curing systems, the ultraviolet curing system has become the mainstream because of its low equipment installation cost and small footprint. [0003] The photopolymerization initiator, which is an essential component in the ultraviolet curing system, is different from the reactive monomer that becomes a high molecular weight substance...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/34B41J2/01B41M5/00C07D295/00C09D11/101C09D11/38
CPCC07C237/34C09D11/101C07D295/033C07C229/38C09D11/36C07C237/20C07D295/192C09D11/107C09D11/38B41J2/01B41M5/50
Inventor 宫本正纪山本誓谷本洋一余语梓近藤明宏山田智和
Owner DIC CORP
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