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WO2002060973A1 - Composition photodurcissable contenant un compose sel iodonium - Google Patents

Composition photodurcissable contenant un compose sel iodonium Download PDF

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Publication number
WO2002060973A1
WO2002060973A1 PCT/JP2002/000689 JP0200689W WO02060973A1 WO 2002060973 A1 WO2002060973 A1 WO 2002060973A1 JP 0200689 W JP0200689 W JP 0200689W WO 02060973 A1 WO02060973 A1 WO 02060973A1
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WIPO (PCT)
Prior art keywords
anthracene
bis
tetrakis
alkyl group
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2002/000689
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English (en)
Japanese (ja)
Inventor
Hiroshi Takahashi
Akihiro Shirai
Shoji Yamaguchi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Soda Co Ltd
Original Assignee
Nippon Soda Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Soda Co Ltd filed Critical Nippon Soda Co Ltd
Publication of WO2002060973A1 publication Critical patent/WO2002060973A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/08—Saturated oxiranes
    • C08G65/10—Saturated oxiranes characterised by the catalysts used
    • C08G65/105—Onium compounds
    • 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

Definitions

  • the present invention relates to a photocurable composition, and more particularly, to a photocurable composition that generates an acid by irradiation with active energy rays such as light, an electron beam, and an X-ray and cures in a short time. Since the cured product of the composition has excellent physical properties, it is suitably used as a paint, an adhesive, a photoresist, an ink, a silicone release and the like. Background technology:
  • Polymerization of a cationic polymerizable compound with an active energy ray-sensitive polymerizable initiator is preferable because it is not affected by oxygen, and therefore, is preferably curable. It is known to use sensitizers to obtain sufficient curing properties for both pigment systems. It is also known that diarylodonium salt is used as an active energy ray-sensitive cation polymerization initiator, and anthracene derivative is used as a sensitizer.
  • Japanese Patent Application Laid-Open No. H10-147680 discloses a polyaromatic compound having at least one hydroxyl group or an optionally substituted aralkyloxy group or alkoxy group as a substituent
  • a photocatalyst composition comprising at least one compound having a UV spectral absorption at a wavelength longer than 330 nm as a sensitizer, which is a compound selected from the group consisting of
  • Japanese Patent Application Laid-Open No. H11-3228952 discloses that, as essential constituents, (1) a force-thione polymerizable organic substance, (2) an energy ray-sensitive cationic polymerization initiator, and (3) General formula
  • R is a hydrocarbon group having 1 to 20 carbon atoms which may contain an oxygen atom or a halogen atom
  • X may contain a hydrogen atom, a halogen atom, or an oxygen atom or a halogen atom.
  • a photopolymerizable composition containing an anthracene derivative represented by the formula: is described, and various onium salts are exemplified as the energy ray-sensitive cationic polymerization initiator.
  • sulfonium salts and odonium salts are preferable, and in the examples, 4,4′-bis (di (S-hydroxyethoxy) phenylsulfonio) phenylsulfidobis-hexafluorophosphine is preferred. It describes a combination with a sulfonium salt such as 1st.
  • the anthracene derivative exemplified in Japanese Patent Application Laid-Open No. H10-147608 has low versatility due to low solubility in various cationically polymerizable compounds, and has insufficient curing properties. There was no problem.
  • An object of the present invention is to provide a photocurable composition which can use various cationically polymerizable compounds and can be sufficiently cured immediately after irradiation.
  • the present inventors have conducted intensive studies to solve the above problems, and as a result, have found that the above problems can be solved by combining a diarydonium salt having a specific structure with an anthracene derivative having a specific structure, thereby completing the present invention. It led to.
  • R 2 each independently represent a C 1 -C 20 alkyl group which may have a substituent
  • R 3 and R 4 each independently represent a halogen atom
  • n and m each independently represent 0 or 1.
  • R 3 or R 4 may be the same or different, respectively, provided that when n and m are 0, and R 2 independently represent a C 4 to C 20 alkyl group which may have a substituent.
  • R 5 represents a straight-chain or branched alkyl group of CC 6
  • R 6 represents a straight-chain or branched alkyl group of C 1 to C 6
  • p represents an integer of 1 to 4, and p is 2 or more.
  • R 6 may be the same or different
  • R 7 represents a linear or branched alkyl group having 1 to 6 carbon atoms
  • q represents an integer of 0 to 4
  • q represents 2 or more.
  • R 7 may be the same or different
  • ⁇ may be of the form
  • R 9 and R 10 each independently represent a hydrogen atom, a C1-C6 linear or branched alkyl group, a phenyl group or an aralkyl group, and s is an integer of 1 or 2.
  • R. may be the same or different
  • R 8 , R u each independently represents a hydrogen atom, a C 1 to C 12 linear or branched alkyl group which may have a substituent, a phenyl group which may have a substituent, Represents an aralkyl group which may be substituted.
  • r represents an integer of 1 to 5, when r is 2 or more, Y may be the same or different, and X is non-nucleophilic Represents an anion residue.
  • R 12 , R 13 , and R 14 each independently represent a C 1 to C 6 linear or branched alkyl group; R 7 represents a linear or branched alkyl group having 1 to 6 carbon atoms; q represents any integer from 0 to 4, and when q is 2 or more, they may be the same or different, and Y is the formula (III)
  • R 9 and each independently represent a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group or an aralkyl group, and s represents an integer of 1 or 2; when but a 2, R 9,., which may be each the same or different, R 8 R u are each independently a hydrogen atom, a an optionally substituted C 1 through C 12 straight-chain or Represents a branched alkyl group, a phenyl group which may have a substituent or an aralkyl group which may have a substituent.) Wherein r is 1 to 5 And when r is 2 or more, Y may be the same or different, and X represents a non-nucleophilic anion residue. )
  • the non-nucleophilic anion residue is SbF 6 , As F 6 , PF 6 , BF 4 or (F 5 C 6 )
  • R 5 , R 6 , R 7 , R 9 , R 10 , R 12 , R 13 , R 14 in formulas (II) and (IV) used in the present invention may be a C1-C6 linear or branched alkyl group. Specifically, methyl, ethyl, n-propyl, isopropyl, n-butyl, isoptyl, sec-butyl, t-butyl, n-pentyl, isopentyl, sec- Examples include a pentyl group, a t-pentyl group, a neopentyl group, an n-hexyl group, and an isohexyl group.
  • the aralkyl group for R 9 and R 1Q represents a benzyl group, a phenyl group or the like.
  • R 8 is a methyl group, Echiru group, n- propyl group, an isopropyl group, n- Bed butyl group, isobutyl group, sec- butyl group, t_ butyl group, n- pentyl group, I Sopenchiru group, sec- It represents an alkyl group having 1 to 12 carbon atoms such as a pentyl group, a t-pentyl group, a neopentyl group, an n-hexyl group, an isohexyl group, a heptyl group and an octyl group.
  • aralkyl group which may have a substituent such as a phenyl group, a benzyl group and a phenyl group which may have a substituent.
  • substituents include halogen atoms such as chlorine, bromine and fluorine, alkyl groups having an ether bond, and hydroxy groups.
  • X is a non-nucleophilic anion residue, SbF 6 , As F 6 , PF 6 , BF 4 or
  • rhododium salt compounds represented by the formulas (II) and (IV) are shown below.
  • X in the formula represents a S b F 6, A s F 6, PF 6, BF 4 or (F 5 C 6) non-nucleophilic Anion residues such 4 B.
  • M represents an aluminum alloy.
  • the reaction of the compounds [a] and [b] with a sulfuric acid catalyst is carried out, if necessary, in an organic solvent such as acetic acid or acetic anhydride at 120 ° C to room temperature for 1 hour to several tens of hours. After the reaction is completed, add water to the reaction solution and stir. The precipitated compound is collected by filtration or extracted with an organic solvent to obtain the compound [c], and the target product [d] is obtained by a salt exchange reaction.
  • an organic solvent such as acetic acid or acetic anhydride
  • the rhododium salt compound represented by the formula (IV) can be produced in the same manner.
  • These rhododium salt compounds can be used as a photoacid generator, and as a photopolymerization initiator, a cationically polymerizable compound can be cured by irradiation with active energy rays such as light, electron beams, and X-rays.
  • Light sources include low-pressure mercury lamps, medium-pressure mercury lamps, and high-pressure mercury lamps. Lamps, ultra-high pressure mercury lamps, metal halide lamps, xenon lamps, carbon arc lamps, etc. are used.
  • Laser beams such as semiconductor lasers, argon lasers, He-Cd lasers, and other ionizing radiations such as ⁇ -rays, / 3-rays, ⁇ -rays, neutrons, X-rays, and accelerating electron beams. Can be easily cured.
  • any cation-polymerizable monomers, oligomers and polymers can be used irrespective of their types, but glycidyl ether type epoxy compounds, alicyclic Examples include oxysilane compounds such as type epoxy compounds and oxetane compounds, and vinyl ether compounds.
  • vinyl compounds include styrene compounds such as styrene, ⁇ -methylstyrene, ⁇ -methoxystyrene, ⁇ -butoxystyrene, methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, Cyclohexyl vinyl ether, 2-chloroethyl vinyl ether, 2-phenyloxyethyl vinyl ether, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, 2-ethylhexylvinyl ether, cyclohexanedimethanol monovinyl ether Alkyl vinyl ether compounds such as, dodecyl vinyl ether, stearyl vinyl ether, 2-acetoxyl vinyl ether, aryl vinyl ether, 2-methacryloyloxeti Alkenyl vinyl ether compounds such as vinyl ether and 2-acryloyl
  • Epoxy compounds include phenylglycidyl ether, p-tert-butylphenyldaricidyl ether, butyldaricidyl ether, 2-ethylhexylglycidyl ether, arylglycidyl ether, 1,2-butylene oxide Side, 1,3-butadiene monooxide, 1,2-dodecylene oxide, epichlorohydrin, 1,2-epoxydecane, ethylene oxide, propylene oxide, styrene oxide, cyclohexane Monofunctional monomers such as xenoxide, 3-methacryloyloxymethylcyclohexenoxide, 3-atalyloyloxymethylcyclohexenoxide, and 3-vinylcyclohexenoxide, 1,13-tetradecadienedioxide , Limonenedioxide, 3, 4-epoxy Chlohexylmethyl mono (3,4-epoxycyclohexylmethyl
  • Bicycloorthoester compounds include 1-phenyl_4-ethyl-2,6,7-trioxabicyclo [2,2,2] octane, 1-ethyl-14-hydroxymethyl-2,6,7-trio Compounds such as xabicyclo [2,2,2] octane are exemplified.
  • the oxetane compounds include 3,3-dimethyloxetane, 3,3-bis (chloromethyl) oxetane, 2-hydroxymethyloxetane, and 3-methyl-oxetane.
  • Ri and R 2 each independently represent a C 1 to C 20 alkyl group which may have a substituent
  • R 3 and R 4 each independently represent a halogen atom or a substituent.
  • Examples of the substituent of the C1-C20 alkyl group or the alkoxy group include halogen atoms such as chlorine, bromine, and fluorine, an alkyl group having an ether bond, a hydroxy group, and an aryl group. Multiple bonds may be included in the alkyl chain.
  • anthracene derivative represented by the formula (I) include 9,10-diphenoxyanthracene, 9,10-di-n-butoxyanthracene, 9,10-di-isobutoxyanthracene, 9 , 10-Gee s-Butoxyanthracene, 9,10-Di-butoxyanthracene, 9,10-Bis (n-pentyloxy) anthracene, 9,10-Bis (isopentyloxy) anthracene , 9,10-bis (1-methylbutyloxy) anthracene, 9,10-bis (t-pentyloxy) anthracene, 9,10-bis (n-hexyloxy) anthracene, 1 0—Bis (isohexyloxy) anthracene, 9, 10 0— Bis (n-heptyloxy) anthracene, 9,10-Bis (n-octyloxy) anthracene, 9,10
  • anthracene derivative can be used in combination with a known sensitizer.
  • Known sensitizers include acridine orange as described in JorunalofPolymerScience: Polymerr Chemistry Edition, Vol. 16, 2441 (1978).
  • Phenol derivatives such as phenol, hydroquinone, 4-methoxy-11-naphthol, 2-hydroxydibenzofuran, 1-naphthol, 2-naphthol, 1-methoxynaphthalene, 2-methoxynaphthalene, 1-hydroxyphenant Ren, Glycidyl 1 naphthyl ether, 2- (2-naphthoxy) ethylvinyl ether, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaph Taren, 1,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 2,7-dimethoxynaphthalene, 1,1'-thio Bis (2-naphthol),
  • thioxanthones which are generally known as a sensitizer for a rhododium salt compound, and various dye derivatives can be used in combination.
  • the compounding ratio of the potassium salt compound represented by the formula (II) or the formula (IV) to the cationic polymerizable compound is 100 parts (parts by weight, hereinafter the same). On the other hand, 0.1 to 20 parts of a rhododium salt compound is preferable, and 0.1 to 10 parts is more preferable. If the amount of the odonium salt compound is small, the curability of the cationically polymerizable compound will be reduced, and if it is excessive, the properties of the cured product will be reduced.
  • the mixing ratio of the anthracene derivative represented by the formula (I) to the cationically polymerizable compound is preferably 0.001 to 10 parts with respect to 100 parts of the cationically polymerizable compound. 0.01 to 5 parts is preferred. If the amount of the anthracene derivative is small, the photoreactivity of a rhododium salt compound used as a photopolymerization initiator is low. If it is excessive, the properties of the cured product deteriorate.
  • the photocurable composition of the present invention contains a pigment, it is used for inks and photoresists.
  • the pigment used in the present invention include black pigments such as carbon black, acetylene black, run black, and aniline black, graphite, zinc yellow, power dom yellow, yellow iron oxide, mineral fast yellow, nickel titanium yellow, and navel.
  • Yellow pigments such as water yellow, naphthol yellow S, hanselow G, hanselow 10G, benzine yellow G, benzine yellow GR, quinoline yellow rake, permanent yellow NCG, tartrazine lake, etc., red lead graphite, molybdenum orange, Orange pigments such as permanent orange GTR, pyrazo orange orange, Vulcan orange, induslen brilliant orange RK, benzidine orange G, induslen brilliant orange range GK, bengala, cadmium red , Lead red, mercury sulfide dorm, permanent thread 4 R, litho red thread, pyrazolone red, watching red calcium salt, lake red D, brilliant carmine 6 B, eosin lake, rhodamine lake B, alizarin lake Red pigments such as Brilliant Power 3B, manganese purple, purple pigments such as Fast Bioreth B, Methyl Biorete Trek, navy blue, cobalt blue, Al Ribe Blue Lake, Victoria Tri-lake Lake
  • Green Pigments zinc oxide, titanium dioxide, antimony white
  • white pigments such as zinc sulfide, and Balai preparative powder, barium carbonate, clay, silica, white Tokabo down, talc, extender pigments alumina white bets like.
  • a radical polymerizable compound can be used.
  • the radical polymerizable compound used in the present invention any monomer, oligomer or polymer having radical polymerizability can be used regardless of its kind, but an unsaturated ester compound is particularly preferable.
  • a monofunctional or polyfunctional acrylate / methacrylate monomer is used.
  • Examples of the mer include epoxy acrylate, epoxy methacrylate, polyester acrylate, polyester methacrylate, polyether acrylate, polyether methacrylate, polyurethane acrylate, polyurethane methacrylate, polybutadiene acrylate, polybutadiene methacrylate, and the like.
  • Examples of the cal polymerizable polymer include acrylates such as polyester, polybutadiene, polyether, urethane, and epoxy, methacrylate compounds, and unsaturated polyesters.
  • radical polymerizable reactive diluent examples include acrylate monomers such as acrylic acid and ethyl acrylate, methacrylate monomers such as methacrylic acid and methyl methacrylate, and styrene.
  • the crystals were suspended in 200 g of ethyl acetate and 100 g of pure water, and 14.0 g of potassium hexafluoroantimonate was added thereto, followed by sufficient stirring.
  • the ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated to dryness to obtain 28.9 g of a white powder. This was identified by NMR.
  • the sensitizer was added in a predetermined amount shown in Table 1 to 100 parts by weight of the resin shown in Table 1, and the mixture was heated to 50 ° C and appropriately stirred.
  • the case where the sensitizer was completely dissolved after the heat treatment for 4 hours and there was no insoluble matter even after leaving at room temperature was shown in Table 1, and the case where an insoluble portion was observed was marked with X in Table 1. Comparative Example 1
  • UVR-6110 Alicyclic epoxy, manufactured by Union Carbide
  • Adeka Optoma KRM-2410 Epibis type epoxy, manufactured by Asahi Denka Kogyo Co., Ltd.
  • EXOA Oxetane, manufactured by Toagosei Co., Ltd.
  • the value in parentheses represents the number of grams dissolved in 100 g of the resin.
  • Example 5 More than Example 5 (MEK rubbing test)
  • UVR-6110 100 parts by weight of UVR-6110, 100 parts by weight of titanium oxide, 2 parts by weight of the odonium salt described in Reference Example 2 as a polymerization initiator, and 9,10-dibutoxyanthracene as a sensitizer Parts were mixed and kneaded in a three-necked mouth.
  • This composition was applied to a tin plate to a thickness of 5 ⁇ m and irradiated with light using a belt conveyor type 160 W gallium-containing metal halide lamp to obtain a cured coating film (belt conveyor speed: 20 m / min) .
  • a wide range of cationically polymerizable compounds can be used by combining the sensitizer of the present invention and a sodium salt.
  • it exhibits excellent photoactivity regardless of whether it is a clear or pigment type, and can cure a cationically polymerizable compound in a short time by irradiation with active energy rays such as light, electron beams, and X-rays. Workability can be greatly improved.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Polymerisation Methods In General (AREA)
  • Epoxy Resins (AREA)

Abstract

L'invention concerne une composition photodurcissable, contenant un quelconque composé parmi plusieurs composés à polymérisation cationique, pouvant durcir immédiatement après irradiation. La composition photodurcissable est caractérisée en ce qu'elle comprend: (1) un dérivé anthracène possédant une structure spécifique représentée par la formule (I), (2) un composé à polymérisation cationique, et (3) un sel diaryliodonium possédant une structure spécifique représentée par la formule (II).
PCT/JP2002/000689 2001-01-31 2002-01-30 Composition photodurcissable contenant un compose sel iodonium Ceased WO2002060973A1 (fr)

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JP2001022657 2001-01-31
JP2001-22657 2001-01-31

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WO2002060973A1 true WO2002060973A1 (fr) 2002-08-08

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1431315A3 (fr) * 2002-12-18 2004-10-13 Tokuyama Corporation Initiateur de photopolymérisation et composition photopolymérisable.

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0927726A1 (fr) * 1996-09-19 1999-07-07 Nippon Soda Co., Ltd. Composition phytocatalytique
JPH11269209A (ja) * 1998-03-24 1999-10-05 Nippon Soda Co Ltd オニウム塩化合物及びそれを含む光硬化性組成物
JPH11279212A (ja) * 1998-02-02 1999-10-12 Nippon Soda Co Ltd 新規ヨードニウム塩化合物を含有する光硬化性組成物
JPH11322900A (ja) * 1998-03-19 1999-11-26 Nippon Soda Co Ltd 光硬化性組成物および硬化方法
JPH11322952A (ja) * 1998-05-15 1999-11-26 Asahi Denka Kogyo Kk 光重合性組成物および硬化塗膜形成方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0927726A1 (fr) * 1996-09-19 1999-07-07 Nippon Soda Co., Ltd. Composition phytocatalytique
JPH11279212A (ja) * 1998-02-02 1999-10-12 Nippon Soda Co Ltd 新規ヨードニウム塩化合物を含有する光硬化性組成物
JPH11322900A (ja) * 1998-03-19 1999-11-26 Nippon Soda Co Ltd 光硬化性組成物および硬化方法
JPH11269209A (ja) * 1998-03-24 1999-10-05 Nippon Soda Co Ltd オニウム塩化合物及びそれを含む光硬化性組成物
JPH11322952A (ja) * 1998-05-15 1999-11-26 Asahi Denka Kogyo Kk 光重合性組成物および硬化塗膜形成方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1431315A3 (fr) * 2002-12-18 2004-10-13 Tokuyama Corporation Initiateur de photopolymérisation et composition photopolymérisable.

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