Oxime ester compound and photopolymerization initiator containing the same

a technology of oxime ester and initiator, which is applied in the direction of photomechanical equipment, instruments, organic chemistry, etc., can solve the problems of insufficient sensitivity of known o-acyl oxime compounds, and achieve the effect of efficient absorption and high sensitivity

Inactive Publication Date: 2009-11-26
ADEKA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0012]The problem to be solved is that there has been no photopolymerization initiator having satisfactory sensitivity.
[0013]Accordingly, an object of the invention is to provide a highly sensitive photopolymerization initiator that efficiently absorbs light of long wavelength, e.g., 405 nm or 365 nm, to be activated.

Problems solved by technology

However, the known O-acyl oxime compounds are not sufficiently satisfactory particularly in sensitivity.

Method used

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  • Oxime ester compound and photopolymerization initiator containing the same
  • Oxime ester compound and photopolymerization initiator containing the same
  • Oxime ester compound and photopolymerization initiator containing the same

Examples

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examples

[0062]The present invention will now be illustrated in greater detail with reference to Examples, but it should be understood that the invention is not deemed to be limited thereto.

examples 1-1 to 1-22

Preparation of compound Nos. 1 to 3, 7, 10, 12, 20, 33, 45 to 51, and 53 to 58

Step 1—Preparation of Acylated Compound

[0063]In a nitrogen atmosphere, 10.4 g (78 mmol) of aluminum chloride and 33.0 g of dichloroethane were put in a reactor. In the same atmosphere, 36 mmol of an acid chloride and then 30 mmol of a nitrocarbazole compound and 33.0 g of dichloroethane were added slowly while cooling with ice, followed by stirring at 5° C. for 30 minutes. The reaction mixture was poured into ice-water for oil-water separation. The solvent was removed to give a desired acylated compound.

Step 2—Preparation of compound Nos. 1 to 3, 7, 10, 12, 20, 33, 45 to 51, and 53 to 58

[0064]In a reactor were charged 20 mmol of the acylated compound obtained in step (1), 2.1 g (30 mmol) of hydroxylamine hydrochloride, and 16.9 g of dimethylformamide and stirred at 80° C. for 1 hour in a nitrogen stream. The reaction system was cooled to room temperature, followed by oil-water separation. The solvent was r...

example 2

Preparation of Photosensitive Composition No. 1

[0065]To 14.0 g of an acrylic copolymer were added 5.90 g of trimethylolpropane triacrylate, 2.70 g of compound No. 1 obtained in Example 1-1, and 79.0 g of ethyl cellosolve, and the mixture was thoroughly stirred to obtain photosensitive composition No. 1.

[0066]The acrylic copolymer used above was obtained by dissolving 20 parts by mass of methacrylic acid, 15 parts by mass of hydroxyethyl methacrylate, 10 parts by mass of methyl methacrylate, and 55 parts by mass of butyl methacrylate in 300 parts by mass of ethyl cellosolve, adding thereto 0.75 parts by mass of azobisisobutyronitrile, followed by heating at 70° C. for 5 hours in a nitrogen atmosphere.

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Abstract

Disclosed is an oxime ester compound represented by the following general formula (I). (In the formula, R1, R2 and R3 independently represent R11, OR11, COR11, SR11, CONR12R13 or CN; R11, R12 and R13 Independently represent a hydrogen atom, an alkyl group having 1-20 carbon atoms, an aryl group having 6-30 carbon atoms, an arylalkyl group having 7-30 carbon atoms or a heterocyclic group having 2-20 carbon atoms; R4 and R5 independently represent R11, OR11, SR11, COR11, CONR12R13, NR12COR11, OCOR11, COOR11, SCOR11, OCSR11, COSR11, CSOR11, CN, a halogen atom or a hydroxy group; and a and b independently represent a number of 0-3.)

Description

TECHNICAL FIELD[0001]This invention relates to a novel oxime ester compound useful as a photopolymerization initiator in a photosensitive composition, a photopolymerization initiator containing the compound as an active ingredient, and a photosensitive composition containing a polymerizable compound having an ethylenically unsaturated bond and the photopolymerization initiator.BACKGROUND ART[0002]A photosensitive composition contains a polymerizable compound having an ethylenically unsaturated bond and a photopolymerization initiator. A photosensitive composition polymerizes to cure on being irradiated with light of 405 nm or 365 nm and is used in photo-curing inks, photosensitive printing plate precursors, and various photoresists.[0003]Patent documents 1 to 8 listed below propose using an O-acyl oxime compound having a carbazolyl structure as a photopolymerization initiator of a photosensitive composition. However, the known O-acyl oxime compounds are not sufficiently satisfactory...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08F2/50C07D209/82
CPCC07D209/88G03F7/031G03F7/0045C08F2/50G03F7/0047G03F7/20
Inventor SAWAMOTO, DAISUKEKIMIJIMA, KOICHIMURATA, KIYOSHIKOZAKI, YASUNORIOISHI, TAKEO
Owner ADEKA CORP
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