WO2001047852A1 - Compose de sel d'onium, composition pouvant etre traitee par energie de rayonnements contenant ledit compose et article traite correspondant - Google Patents

Compose de sel d'onium, composition pouvant etre traitee par energie de rayonnements contenant ledit compose et article traite correspondant Download PDF

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Publication number
WO2001047852A1
WO2001047852A1 PCT/JP1999/007332 JP9907332W WO0147852A1 WO 2001047852 A1 WO2001047852 A1 WO 2001047852A1 JP 9907332 W JP9907332 W JP 9907332W WO 0147852 A1 WO0147852 A1 WO 0147852A1
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Prior art keywords
phenyl
group
bis
tris
tetrakis
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PCT/JP1999/007332
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English (en)
Japanese (ja)
Inventor
Seiichi Hayashi
Rieko Koike
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Nippon Kayaku Kabushiki Kaisha
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Priority to JP11194134A priority Critical patent/JP2000119308A/ja
Priority to JP20161399A priority patent/JP4518594B2/ja
Application filed by Nippon Kayaku Kabushiki Kaisha filed Critical Nippon Kayaku Kabushiki Kaisha
Priority to PCT/JP1999/007332 priority patent/WO2001047852A1/fr
Publication of WO2001047852A1 publication Critical patent/WO2001047852A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • the present invention relates to an onium salt type compound having a novel structure, a photoreaction initiator comprising the same, an energy ray-curable composition containing the same, which can be cured by irradiation with energy rays, and a cured product thereof. It does.
  • Photopolymerizable compositions have been actively studied in the fields of printing inks, paints, coatings, liquid resist inks, etc. from the demands of energy saving, space saving, and pollution-free properties, and their practical use has been realized. It has been considered. However, most of these studies were based on the radical polymerization of double bonds. Cationic polymerizable substances, for example, vinyl ether resin, are materials with excellent physical properties, but are less toxic, have better performance, and are ready for practical use for photopolymerization. There were few agents.
  • oxime compounds having a porate anion such as tetrakis (pentafluorophenyl) porate
  • a porate anion such as tetrakis (pentafluorophenyl) porate
  • hexafenolerophosphonate anion and hexafluoro mouth antimonone No. 6,184,170 and International Patent No. 95/033 show that they exhibit better properties as a photopolymerization initiator than anonymous salt, which is referred to as tonion. It was made clear by the publication of No. 338. According to these public relations and the papers of C. Priou et al., Po 1 ym Mater. Sci. Eng., Vol. 72, p.
  • the two-drug dentotrakis (pentafluorofluorophenyl) por- tate is used for the polymerization of epoxi-silicon, even with the conventional difluoro-denimex hexafluoroantimonate. It has been reported to be more effective. However, the phoenimoleates reported in these documents do not have sufficient solubility in vinyl ether. From the standpoint of improving compatibility, J. A. Dougherty reported in Giarello, Proceeding of Rad Tech '96, North America, Nashville (1996), p. A case was reported in which a long-chain hydrocarbon group was introduced into the aryl group of a single-donium salt. C. Priou et al. Sci. Eng., Vol. 72, pp. 417 (1995) shows that an octyloxy group is added to the aryl of a denim salt. It reports an example of introduction.
  • An object of the present invention is to provide a novel photopolymerization that has improved the disadvantages of conventional photopolymerization initiators (for example, poor solubility in monomers, poor storage stability, coloring, etc.).
  • An object of the present invention is to provide a reaction agent, an energy ray-curable composition curable by irradiation with energy rays containing the same, and a cured product thereof.
  • the present inventors have intensively studied and studied to achieve the above object, and as a result, have developed a novel photopolymerization initiator excellent in compatibility with resins and the like, and a composition using the same has a storage stability.
  • the present inventors have found that an energy ray-curable composition having excellent curability and having no odor in the cured product can be provided, and the present invention has been completed.
  • the cation part has the formula (1)
  • R represents an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a benzyl group, an acyl group or a silyl group
  • X represents an ether bond, a thioether bond, a carbonyl group, an ester bond.
  • Q is the first of a periodic table such as I, S, Se, P or N.
  • a rv represents a carbocyclic, heterocyclic or condensed polycyclic aromatic ring, and n represents an integer from 1 to 200. Represent.
  • one X — is an asymmetric bond
  • R (0 CH 2 CH 2 ) n O — and the above benzene ring or naphthylene ring are bonded to an arbitrary bonding group of one X — It is assumed that ]
  • M represents As, P, Sb, or B
  • Y represents a hydrogen atom, polyhalogenoaryl, or polyhalogenopoly (trifluoromethyl).
  • I an aryl group, and m is an integer of 4 to 6.
  • R in the cation moiety represented by the formula (1) include a methyl group, an ethyl group, and a methyl group.
  • Port Alkyl groups such as pill, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, cyclobutyl, cyclobutyl, etc.
  • one X— in the formula (1) include ether bond, thioether bond, or carbonyl group, thiocarbonyl bond, oxycarbonyl bond, and thiocarbonyl bond bond.
  • Azo bond or sililene bond dimethylsilylene bond, diphenylsilylene bond, dimethoxysilylene bond, etc.
  • An ether bond, a thiol bond, a carbonyl group, and a methylenoxy bond are preferable, and an ether bond and a methylenoxy bond are particularly preferable.
  • R (0 CH 2 CH a) n 0-(hereinafter represented by A) and a benzene ring or a naphthene-lens ring (hereinafter, referred to as A) Is represented by B.) is bonded to an arbitrary bonding group of 1 X—. That is, taking the case where one X— is one CH 20 — as an example, the onium salt type compound of the present invention has a cation moiety represented by the following formula (111) or (1-2): (In the formulas (1-1) and (1-2), Q and Ar have the same meanings as in the formula (1).)
  • the cation moiety of the sodium salt type initiator of the present invention is represented by the formula
  • Q is I (iodine) is a symmetric or asymmetric diary, and one aryl is phenyl or condensed.
  • a specific example of the cation moiety in which Q is I (iodine) in the formula (1) is [4-1 (1,4,7-trioxaoctyl) phenyl] phenylidene.
  • aryl is a phenyl or condensed aromatic ring which is an essential substituent.
  • the remaining aryl groups are carbocyclic or heterocyclic and may be unsubstituted or variously substituted.
  • Functional groups e.g., alkyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, aryloxy, acyl, benzoyl, carboxyl, ester, mercapto, Nitro, cyano, fluoro, black mouth, promo, ground, etc.
  • the cationic portion of the onium salt type compound of the present invention is as described above. Selected from the 15th to 17th groups of the periodic table, such as Se, P, N, etc., in place of 1+ and S + of the red and blue ions A cation of one or more elements may be used.
  • Y in the anion portion represented by the formula (2) include a fluorine atom, a pentaphenylenephenyl group, and a tetraalkyl group.
  • a preferable atom of M is Sb or B.
  • M is Sb
  • Y is a fluorine atom.
  • B is a Y
  • Examples of the anion portion of the hondium salt type compound of the present invention include hexaforenolo arsenene toion and hexofurofluorophosphonate.
  • Tri-fluoro phenyl Tri-fluorate ion, (Tri-fluoro tri-fluorate) Tri-fluoro tie ON, (Fluoro-Tro-cro-Fan) Tri-Fluoro-Bole-To-Ion, (Promote-Tro-Fluoro-Fen) Tri-Fluoro Pole ion, (dibromotrifluorophenyl) Trifluorate ion, (difluorotrifluorophenyl) trif Tri-fluoro robot ion, (Trifluorofluoro-ion), (Trifluorofluoro-ion), (Bromo-chloro trifluorene) ) Trifluoro Robot Ion, (Bromo Fluorofluorophenyl) Trifluoro Roll Ion, (Bromo Fluoro) (Re-closure mouth) tri-fluoro-ion ion, (jibromokur
  • anion parts are hexafluoroarsenate ion, hexafluorophosphate ion, and peony.
  • the hondium salt-type compound of the present invention may be a salt of a cation moiety (halogenated compounds such as tosylate, chloride, bromide, and iodide, hexafluorophosphate, and hexafluorophosphate). Fluoroantimonate, tetrafluoroborate, etc. and alkali metal salts of anion (sodium, lithium, calcium or cesium) ) Can be produced by an exchange reaction with As the reaction solvent, use water, acetate, methylethyl ketone, alcohol, methylene chloride, cross-hole form, or a mixture of these. I can do it.
  • a cation moiety halogenated compounds such as tosylate, chloride, bromide, and iodide, hexafluorophosphate, and hexafluorophosphate.
  • the precipitate is collected by filtration and dried under vacuum.
  • the target substance can be obtained by drying the extract with a drying agent such as sodium sulfate and magnesium sulfate, and then distilling off the solvent.
  • the salt in the cation portion can be synthesized, for example, by the following method.
  • formula In the above (1) when X is an ether bond or a thioether bond, a compound known as a method for synthesizing a Williamson ether is used.
  • alkyl or aryl chlorides, bromides, and iodides are introduced to introduce polyethylene glycol chains.
  • the alkyl halide and the allenoxide having a polyethylene glycol chain are allenoxides (for example, phenoxide, naphthoxide).
  • thiophenoxides and a method of reacting an halogenated aromatic compound with an alkoxide dioxide having a polyethylene glycol chain.
  • the halogeno aromatic compound is activated by an electron-withdrawing group (for example, a nitro group, a cyano group, a trifluoromethyl group, etc.), the latter method is used. However, if not, the former method is suitable.
  • hydroxy (tosyloxy) chloride is added to an array having a polyethylene glycol chain with an acid catalyst (eg, acetic acid, hydrochloric acid). , Lewis acid, etc.) to give the corresponding diaryl dendrites.
  • an acid catalyst eg, acetic acid, hydrochloric acid. , Lewis acid, etc.
  • one of the features of the sodium salt type compound of the present invention is that it has a polyethylene glycol chain in its cation portion.
  • Alkali metal salts in the anion are commercially available (hexafluoroarsenate, hexafluorophosphate, pentafluoroantimonate, tetrate). Other than lafluoroborate, etc., are known methods, and can be used in the form of haloborates (eg, boron trifluoride or trichloride). Boron or their ethers) and organometallic compounds having the desired aryl groups (for example, aryl metal compounds such as magnesium, lithium, and tin). 9, 1131, 1968, and can be synthesized according to the method described in Shiramoto Chemical Journal, 90, 300, 1969) Can be manufactured. It can be converted to an alkali metal salt other than lithium by reacting with an aqueous solution of another alkali metal halide.
  • haloborates eg, boron trifluoride or trichloride
  • organometallic compounds having the desired aryl groups for
  • the thus-obtained onium salt-type compound of the present invention include [(methoxetoxy) phenyl] phenyldimethylhexafluoro. Al arsenate, [(methoxhetoxy) phenyl] phenyl fluorene phosphate,
  • the thus-obtained onium salt type compound of the present invention can be used as a catalyst, a radical generator, a reagent for organic synthesis, a photopolymerization initiator, and a thermal polymerization initiator.
  • a catalyst a radical generator, a reagent for organic synthesis, a photopolymerization initiator, and a thermal polymerization initiator.
  • it has excellent compatibility with resins, and it is preferable to use it as a photopolymerization initiator because it is soluble in not only epoxy compounds but also vinyl ether compounds.
  • the energy ray-curable composition of the present invention (hereinafter, simply referred to as the curable composition of the present invention) will be described.
  • the curable composition of the present invention is characterized in that it comprises Contains cationic polymerizable substances.
  • Examples of the cationic polymerizable substance used in the present invention include a vinyl group having an electron density higher than that of a vinyl group having an electron donating group.
  • Examples of the cationic polymerizable vinyl ether compound include, for example, triethylene glycol vinyl ether, tetraethylene glycol divinyl ether, dipropylene Recohol divinyl ether, tripropylene glycol divinyl ether, cyclohexane-1,4,4-dimethylol divinyl ether, 1,4-butane Diol vinyl ether, 1,6-hexane diol divinyl ether, trimethyl propyl nitrone vinyl ether, pentaerythritol tertravinyl ether, Zipen evening Methyl diol vinyl ether and the like can be mentioned.
  • Examples of the epoxy compound include conventionally known aromatic epoxy compounds, aliphatic epoxy compounds, alicyclic epoxy compounds, monofunctional epoxides, and monofunctional episulfide compounds. And the like.
  • aromatic epoxy compound a polyhydric phenol having at least one aromatic ring or a polyglycidyl ether of an alkylenoxyside adduct thereof is used.
  • bisphenol compounds such as bisphenol A, bisphenol F and bisphenol S or bisphenol compounds are used.
  • Alkylenoxide eg, ethylene oxide, brovirenoxide, butylene oxide, etc.
  • Alkylenoxide eg, ethylene oxide, brovirenoxide, butylene oxide, etc.
  • adducts by reacting adducts with epichlorohydrin Glycidyl ethers, novolak epoxy compounds (eg, phenol nopoloxy epoxy compounds, cresol nopoloxy epoxy compounds, bromine) Chemical phenol-Nopolak Epoxy compound), Application Benefits scan full et Bruno Rume data down preparative rig glycidyl ether like et be.
  • novolak epoxy compounds eg, phenol nopoloxy epoxy compounds, cresol nopoloxy epoxy compounds, bromine
  • Chemical phenol-Nopolak Epoxy compound Chemical phenol-Nopolak Epoxy compound
  • Application Benefits scan full et Bruno Rume data down preparative rig glycidyl ether like et be.
  • aliphatic epoxy compounds include polyhydric alcohol
  • Diglycidyl ethers of diols 1, 6—Hexane Diglycidyl ether of diol, triglycidyl ether of glycerin, triglycidyl ether of trimethylolpropane, polyethylene glycol ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Add one or more alkylene oxides of aliphatic polyhydric alcohols such as phosphorus (for example, ethylene oxide, propylene oxide, butylene oxide, etc.)
  • the alicyclic epoxy compound include a polyether polyol, a polyether polyol, and an alicyclic epoxy compound.
  • Hexylmethyl-1,3-epoxy Hexane carboxylate bis (3,4-epoxycyclohexylmethyl) adipate, 2 — (3,4-epoxycyclohexyl) 5,5 — Spiro 1,3,4—epoxy) cyclohexanone, meta-dioxane, bis (2,3—epoxycyclopentyl) ether, etc.
  • epoxide examples of monofunctional compounds are the monoglycidyl ethers of higher aliphatic alcohols, phenol and cresol, butyl phenol, and these alcohols. Monoglycidyl ether of polyester alcohol obtained by adding lenoxide It is mentioned.
  • Examples of the monofunctional episulfide include a sulfur analog in which the epoxy ring of the compound exemplified as the monofunctional epoxide is changed to an epoxide ring.
  • Examples of the cyclic ether compound include oxetane, phenyloxen, and other tetraxylamines, tetrahydrofuran, and 2-methylthiohydran. , Etc. Tetrahydropyrans, Tetrahydropyrans, 3 — Propylte Tetrahydropyrans, etc. and s — Trioxane and the like.
  • Examples of lactones include:-probiolactone, acetyl lactone, one-stroke lactone, and ⁇ - ⁇ 'reloractone.
  • Examples of the oxazolins include oxazozolin, 2-phenyloxyzolin, 2-decyloxazolin and the like.
  • Examples of the aziridines include aziridines, ⁇ -ethyl aziridines, and the like.
  • Examples of cyclosiloxanes include hexamethyltricyclohexane, octamethylcyclotetrasiloxane, and triphenyl trimethylcyclo. Rishirokisan etc. are mentioned.
  • Examples of the cyclic acid anhydride include, for example, hydrofluoric anhydride, maleic anhydride, and succinic anhydride. Examples of lacquers include?
  • cation polymerizable compounds may be used alone or as a mixture of two or more kinds, or may be a hybrid compound having two or more cation polymerizable functional groups in one compound.
  • the curable composition of the present invention contains 0.01 to 20 parts by weight of the onium salt type compound of the present invention as an essential component with respect to 100 parts by weight of the cationically polymerizable substance.
  • the cation salt compound is previously dissolved in a suitable solvent (for example, propylene carbonate, carbitol, carbitol acetate, butyrola). Dissolved in water, etc.).
  • the curable composition of the present invention can be prepared by a method such as mixing, dissolving or kneading a cation polymerizable substance and an onium salt type compound.
  • the curable composition of the present invention is usually exposed to an energy ray such as ultraviolet rays for 0.1 second to a few minutes to dry or to dry the touch. It can be cured to a solvent-insoluble state.
  • a suitable energy line may be any as long as it induces the decomposition of the onium salt compound of the present invention, but is preferably ultrahigh, high, medium, or low.
  • Use high-energy radiation such as electromagnetic wave energy, electron beams, X-rays, and radiation having wavelengths of You.
  • the exposure time to the energy ray depends on the strength of the energy ray, the coating thickness and the cationic polymerizable substance, but usually about 0.1 to 10 seconds is sufficient.
  • composition of the present invention further includes a click.
  • a solvent for dilution, a non-reactive or (meth) acrylic acid ester compound for reforming, and the like can be blended as long as the on-polymerization is not impaired.
  • optical radical initiators for example, 1-hydroxycyclohexyl phenyl ketone, acetophen
  • benzoyl methyl ether or benzoyl methyl ether it is preferable to use benzoyl methyl ether or benzoyl methyl ether.
  • organic carboxylic acids or acid anhydrides may be added to improve electrical properties, or polymer or other flexible materials may be added to provide rubber elasticity. Repolymers can also be mixed.
  • the onium salt type compound of the present invention by being combined with a sensitizer, enhances the activity against energy lines and can be used as an ultra-sensitive thione generator composition having photosensitivity. And can be done.
  • the sensitizer include naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, naphthacene derivatives, perylene derivatives, Condensed polycyclic aromatic derivatives such as pentacene derivative, hexacene derivative, heptane derivative, etc., fluorene derivative, naphthoquinone derivative, anthraquinone derivative, benzoyl derivative Derivatives, xanthane derivatives, thioxanthen derivatives, xanthonone derivatives, thioxantone derivatives, coumarin derivatives, cyanin derivatives, melocyanin derivatives, Acrylidine derivatives, indolin derivatives, azulene derivatives, porphyrin derivatives
  • the curable composition of the present invention is usually used as a transparent liquid, but depending on the application, it may be an inert organic or inorganic pigment, a dye, an anti-capri agent, an anti-fading agent, Anti-halation agents, optical brighteners, surfactants, plasticizers, flame retardants, antioxidants, fillers, antistatic agents, defoamers, flow regulators, accelerators, retarders, It can also be used as a mixture with light stabilizers, fungicides, antibacterial agents, magnetic substances, and organic solvents for dilution.
  • the curable composition of the present invention can be used for metal, wood, rubber, plastic, glass, ceramic products and the like. Further, specific uses of the present invention include paints, coating agents, inks, photo resists, liquid resists, electrophotography, and direct printing plate materials. Hologram materials, adhesives, adhesives, adhesives, adhesives, sealants, molding materials, casting materials, putties, glass fiber impregnating agents, sealing agents, and the like.
  • a reflux condenser, a thermometer, and a dropping funnel with a calcium chloride tube attached to the 300 ml tri-loaf port were installed. 8.6 g (0.215 mol) of lithium was weighed out, the oil was thoroughly washed with pentane, and the solvent was distilled off under reduced pressure. Then, add 100 ml of anhydrous dimethyl acetate amide (DMAc), While stirring with a magnetic stirrer, 35 g (0.2 mol) of DMA c was added from the dropping funnel to the tri-ethylene glycol monomethyl ester.
  • DMAc dimethyl acetate amide
  • DMAc dimethyl acetate amide
  • Example 1 [4- (1,4,7-trioxaoctyl) phenyl] phenylidene tosylate was replaced with [4-1 (1,4,7) obtained in Synthesis Example 5. , 10 —tetraxanedecyl) phenyl] phenylphosphonate (1.23 g, 2 mmo 1) was reacted and worked up in the same manner to give [4— ( 1, 4,7,10 —tetraxandedecyl) phenyl] phenyl hexafluoroantimonate (a compound of the present invention, a compound of the present invention, compound No. 6 in Tables 1 and 2) 1.35 g I got Yield 99%.
  • Example 5 [4-((1,4,7-trioxaoctyl) phenyl] phenyl-dunimutate] trakis [4-1 (trifluoromethyl) -2,3,5,6—tetrafluorophenyl] borate Synthesis of In a 300 ml Erlenmeyer flask, 1.14 g of [4- (1,4,7-trioxaoctyl) phenyl] phenyl-donium-to-silyl compound obtained in Synthesis Example 4 ( Take 2 mmol) and 50 ml of acetone and stir with a magnetic stirrer.
  • Ethyl-donium tetrakis [4— (trifluoromethyl) -12,3,5,6—tetrafluorophenyl] porate (onium salt compound of the present invention, Table 1, 3) 2.2 g of compound No. 2 were obtained. Yield 86%.
  • Example 8 [4— (1,4,7,10—tetraoxane decyl) phenyl] phenyl 1-tetramethyltetrakis (2,4,6—tri- Synthesis of Fluoro 3,5—Dichlorophenyl) Pore To 300 ml of triangular flask was added [4— (1,4,7,10—tetraxane). [Desil) phenyl] phenyl benzene 1.18 g (3 mmol) and 100 ml of acetone were taken and stirred with a magnetic stirrer.
  • Acetonitrile 25 ml solution The mixture was added dropwise, and stirred overnight while being shielded from light. The insoluble material was separated by filtration, and the solvent was distilled off from the filtrate under reduced pressure. Ether was added to the residue, ether-insoluble matter was separated by filtration, and the solvent was distilled off from the filtrate under reduced pressure and vacuum to give [4-1 (1,4,7,10-tetraoxazin).
  • the onium salt type compound of the present invention is excellent in compatibility with cationically curable compounds, has excellent storage stability, has no odor, has a high curing speed, and is excellent in curing properties, and is suitable as a photopolymerization initiator. Can be used for Further, the energy ray-curable composition containing the onium salt type compound of the present invention has no coloring of the cured coating film and gives a transparent and excellent physical properties.

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Abstract

L'invention concerne un réactif photopolymérisable qui présente une excellente compatibilité avec des composés pouvant être traités sur le plan cationique, une toxicité faible et qui est indolore, une composition contenant le réactif et pouvant être traitée suite à une exposition à l'énergie rayonnante. Ledit réactif est un composé de sel d'onium qui comprend une partie cationique renfermant une chaîne de polyéthylèneglycol.
PCT/JP1999/007332 1998-07-17 1999-12-27 Compose de sel d'onium, composition pouvant etre traitee par energie de rayonnements contenant ledit compose et article traite correspondant WO2001047852A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP11194134A JP2000119308A (ja) 1998-07-17 1999-07-08 オニウム塩型化合物、これを含有するエネルギ―線硬化性組成物及びその硬化物
JP20161399A JP4518594B2 (ja) 1998-07-17 1999-07-15 オニウム塩型化合物、これを含有するエネルギー線硬化性組成物及びその硬化物
PCT/JP1999/007332 WO2001047852A1 (fr) 1998-07-17 1999-12-27 Compose de sel d'onium, composition pouvant etre traitee par energie de rayonnements contenant ledit compose et article traite correspondant

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Application Number Priority Date Filing Date Title
JP20243398 1998-07-17
JP11194134A JP2000119308A (ja) 1998-07-17 1999-07-08 オニウム塩型化合物、これを含有するエネルギ―線硬化性組成物及びその硬化物
PCT/JP1999/007332 WO2001047852A1 (fr) 1998-07-17 1999-12-27 Compose de sel d'onium, composition pouvant etre traitee par energie de rayonnements contenant ledit compose et article traite correspondant

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Cited By (1)

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JP2018065873A (ja) * 2016-03-24 2018-04-26 三菱ケミカル株式会社 電子受容性化合物及び電荷輸送膜用組成物、それを用いた発光素子

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US20030108810A1 (en) * 2001-08-22 2003-06-12 Williamson Sue Ellen Deodorizing agent for sulfur- or nitrogen-containing salt photoinitiators

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US5468890A (en) * 1991-12-20 1995-11-21 Wacker-Chemie Gmbh Iodonium salts and process for the preparation thereof
JPH10245378A (ja) * 1997-02-28 1998-09-14 Nippon Kayaku Co Ltd 新規スルホニウム塩、それからなる光重合開始剤及びエネルギー線硬化性組成物

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JPH10245378A (ja) * 1997-02-28 1998-09-14 Nippon Kayaku Co Ltd 新規スルホニウム塩、それからなる光重合開始剤及びエネルギー線硬化性組成物

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JP2018065873A (ja) * 2016-03-24 2018-04-26 三菱ケミカル株式会社 電子受容性化合物及び電荷輸送膜用組成物、それを用いた発光素子
JPWO2017164268A1 (ja) * 2016-03-24 2018-07-05 三菱ケミカル株式会社 電子受容性化合物及び電荷輸送膜用組成物、それを用いた発光素子
CN108884114A (zh) * 2016-03-24 2018-11-23 三菱化学株式会社 电子接受性化合物和电荷传输膜用组合物、使用其的发光元件
JP2018203745A (ja) * 2016-03-24 2018-12-27 三菱ケミカル株式会社 電子受容性化合物及び電荷輸送膜用組成物、それを用いた発光素子
JP2022009119A (ja) * 2016-03-24 2022-01-14 三菱ケミカル株式会社 電子受容性化合物及び電荷輸送膜用組成物、それを用いた発光素子
JP7006304B2 (ja) 2016-03-24 2022-01-24 三菱ケミカル株式会社 電子受容性化合物及び電荷輸送膜用組成物、それを用いた発光素子
CN108884114B (zh) * 2016-03-24 2022-02-25 三菱化学株式会社 电子接受性化合物和电荷传输膜用组合物、使用其的发光元件
US11316112B2 (en) 2016-03-24 2022-04-26 Mitsubishi Chemical Corporation Electron-accepting compound and composition for charge-transporting film, and luminescent element using same
US11793069B2 (en) 2016-03-24 2023-10-17 Mitsubishi Chemical Corporation Electron-accepting compound and composition for charge-transporting film, and luminescent element using same

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