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WO1999003930A1 - Composition pour revetements durcissant sous l'effet de radiations - Google Patents

Composition pour revetements durcissant sous l'effet de radiations Download PDF

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Publication number
WO1999003930A1
WO1999003930A1 PCT/NL1998/000382 NL9800382W WO9903930A1 WO 1999003930 A1 WO1999003930 A1 WO 1999003930A1 NL 9800382 W NL9800382 W NL 9800382W WO 9903930 A1 WO9903930 A1 WO 9903930A1
Authority
WO
WIPO (PCT)
Prior art keywords
radiation
tertiary amine
coating composition
maleimide
aliphatic
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/NL1998/000382
Other languages
English (en)
Inventor
Aylvin Jorge Angelo Athanasius Dias
Johan Franz Gradus Antonius Jansen
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.)
Koninklijke DSM NV
Original Assignee
DSM NV
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 DSM NV filed Critical DSM NV
Priority to KR1020007000408A priority Critical patent/KR20010021844A/ko
Priority to CA002297056A priority patent/CA2297056A1/fr
Priority to EP98932622A priority patent/EP0996680A1/fr
Priority to BR9811515-4A priority patent/BR9811515A/pt
Priority to JP2000503147A priority patent/JP2001510220A/ja
Priority to AU82457/98A priority patent/AU8245798A/en
Publication of WO1999003930A1 publication Critical patent/WO1999003930A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds

Definitions

  • the invention relates to a radiation- curable coating composition containing a radiation- curable resin composition and an aliphatic maleimide.
  • Such a radiation-curable coating composition is described in "Initiator free polymerisations of donor acceptor monomer systems" by C.E. Hoyle, S. Jonsson, S.C. Clark, C. Miller and M. Shimose (Radtech Europe, June 97, Lyons). This describes a coating composition consisting of an acrylate-functional resin and an aliphatic maleimide. This composition cures under the influence of UV light.
  • a drawback of such a coating composition is that it cures at a low rate.
  • the aim of the invention is to provide a radiation-curable coating composition that has a higher curing rate.
  • the radiation-curable coating composition also contains a tertiary amine. This ensures that the radiation-curable coating composition cures faster under the influence of radiation than the known radiation-curable coating composition described by Hoyle et al .
  • EP-A-618,237 describes a coating composition based on an acrylate-functional resin and maleic anhydride. A drawback of the coating composition described in EP-A-618,237 is that it cures slowly, as a result of which the cured coating may also contain residual monomer in addition to residual photoactive compound.
  • the radiation-curable resin composition consists of for example a reactive unsaturation connected to an electron-withdrawing group (a) , optionally combined with a reactive unsaturation connected to an electron-donating group (b) or a an allyl group-containing compound connected to an electron-donating group (c) or a mixture hereof (b+c) .
  • the reactive unsaturation connected to an electron-withdrawing group (a) is characterised by the following structural element.
  • X may be for example any one of the following groups: OR 4 , NR 4 R 5 , SR 4 .
  • Ri,R 2 , R 3 may be for example independently of one another the following groups: H, C 1 -C 20 alkyl, aryl, substituted aryl, COOR 6 , CONR 6 R 7 , CH 2 COOR 6 , CH 2 OR s , OR 6 , NR 6 R 7 , SR 6 , Cl or CN, in which R 4 , R 5 , R 6 and R 7 are chosen from the following groups: H, C 1 -C 20 , alkyl (including linear and cyclic structures) , aryl, substituted aryl, O, S, N or P atoms-containing heterocyclic compounds, 0, S, N or P atoms-containing aromatic heterocyclic compounds, COY, CH 2 COY, CH 2 OY, CH 2 NYZ, CH 2 SY, CH 2 CH 2 0Y, CH 2 CH 2 NYZ CH 2 CH 2 SY,
  • Y and Z can for example be chosen from any of the following groups H, C 1 -C 20 , alkyl (including linear and cyclic structures) , aryl, substituted aryl, 0, S, N or P atoms-containing heterocyclic compounds, 0, S, N or P atoms-containing aromatic heterocyclic compounds. Derivatives of these compounds can also be used, for example esters, urethanes, urea, thiourethanes and anhydrides.
  • the reactive unsaturation connected to an electron-donating group (b) use is preferably made of a vinyl ether, a vinyl ester, a vinyl amide, a vinyl amine, a vinyl thioether or a vinyl thioester.
  • allyl group-containing compound connected to an electron-donating group use is preferably made of an allyl ether, an allyl ester, an allyl amine or an allyl amide.
  • the amount of reactive unsaturation connected to an electron-withdrawing group (a) in the radiation-curable curing resin is between 25% and 100%.
  • the amount of reactive unsaturation connected to an electron-donating group (b) or an allyl group- containing compound connected to an electron-donating group (c) or a mixture hereof (b+c) in the radiation- curable curing resin is between 0% and 75%, depending on the amount of reactive unsaturation connected to an electron-withdrawing group (a) in the radiation-curable curing resin.
  • the amount of reactive unsaturation connected to an electron-withdrawing group (a) in the radiation-curable resin is 100%.
  • the amount of reactive unsaturation connected to an electron-withdrawing group (a) in the radiation-curable resin is 50% and the amount of reactive unsaturation connected to an electron-donating group (b) or an allyl group-containing compound connected to an electron-donating group (c) or a mixture hereof (b+c) in the radiation-curable resin is 50%.
  • the reactive unsaturation connected to an electron-withdrawing group (a) may be connected to polymers or oligomers via R 4 .
  • polymers or oligomers are polyurethanes , polyesters, polyacrylates, polyethers, polyolefins containing for example units from the group comprising ethylene, propene, butadiene and styrene, hydrocarbon polymers such as (co)polymers of cyclopentadiene, polysilicates, polycarbonates, polyvinyl esters, rubbers such as polyisoprene, natural rubbers and polyepoxides .
  • Copolymers such as polyether urethanes, polyester urethanes, polyether carbonates and polyepoxide esters. Combinations of polymers or oligomers can also be used.
  • the reactive unsaturation connected to the electron-withdrawing group (a) has another functionality besides R 4 , in the form of R lf R 2 or R 3 , for example C00R 6 , C0NR 6 R 7 , CH 2 COOR 6 or CH 2 OR 6
  • the reactive unsaturation can be incorporated in the polymer or oligomer chain.
  • examples of such polymers or oligomers are unsaturated polyesters in which fumarate, maleate, itaconate, citraconate or mesaconate functionalities are incorporated in the structure of the polymer or oligomer.
  • the number of reactive unsaturations connected to an electron- attracting group in a polymer or oligomer is greater than 1.
  • the reactive unsaturation connected to an electron-donating group (b) or the allyl group- containing compound connected to an electron-donating group (c) can be bound to the polymers or oligomers described above via ether, ester amine or amide bonds, or, in the case of a bifunctional reactive unsaturation connected to an electron-donating group or a bifunctional allyl compound, it can also be incorporated in a polymer or oligomer chain.
  • the radiation-curable resin composition may also contain low-molecular compounds containing a reactive unsaturation.
  • These low-molecular compounds contain a * reactive unsaturation in the molecule with side groups that may be aromatic, aliphatic or cycloaliphatic.
  • These molecules may furthermore contain several functionalities, i.e. they may be mono- or multifunctional.
  • ethyl acrylate ethyl methacrylate, methyl methacrylate, hexane diol diacrylate, hexane diol dimethacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate
  • acrylamides such as acrylamide, N- methyl acrylamide, N-lauryl acrylamide, maleate esters such as ethyl maleate, diethyl maleate, methyl maleate, maleamides such as N,N' -bismaleamide, N,N' -dimethyl maleamide, fumarate esters such as ethyl fumarate, diethyl fumarate, fumaric amides, itaconic esters such as methyl itaconate, dimethyl itaconate, ethyl itaconate, itaconic amides, itaconic imides, citraconic esters such as methyl citraconate, diethy
  • Aliphatic maleimides are characterised in that an aliphatic carbon is connected to the nitrogen atom of the maleimide, as represented in the following structure.
  • R- L , R 2 , R 3 independently of one another, a choice can be made from for example the group comprising H, C x - C 20 alkyl, aryl, hydroxy, thiol, amines, ethers, thioethers, esters, thioesters, amides, thioamides, urethanes, thiourethanes and combinations of these functionalities.
  • R l R 2 , R 3 may also form part of ring systems or they may be interconnected in this way, for example so that R ! -R 2 is C 5 H 10 and R 3 is H, i.e. cyclohexyl maleimide.
  • the aliphatic maleimide may also contain more than one maleimide group, i.e. a bis, tris, tetra, penta, hexa, etc. maleimide. If the aliphatic maleimide contains more than one maleimide group, these maleimide groups may be connected via a chain comprising exclusively carbon. These maleimide groups may also be connected via other functionalities, such as amines, ethers, thioethers, esters, thioesters, amides, thioamides , urethanes and thiourethanes . The other functionalities may form part of oligo (polymer) chains such as polyethers, polyesters, polyurethane, polyethylene. Combinations of functional groups are also possible here, such as a polyether urethane.
  • the aliphatic maleimide contains more than one maleimide group. According to a third preferred embodiment of the invention the aliphatic maleimide contains more than one maleimide group and a hydroxy, ether, ester or urethane functionality or combinations of these functionalities .
  • the amount of maleimide in the present radiation-curable coating composition is not critical. Preferably the amount of maleimide used in this radiation-curable coating composition is between 0.1 and 15 wt.%, relative to the radiation-curable resin composition. With less than 0.1 wt.% maleimide the radiation-curable coating composition reacts too slowly. With more than 15 wt.% the properties of the cured radiation-curable coating composition are adversely affected.
  • the tertiary amine may be an aromatic or an aliphatic tertiary amine.
  • An advantage of an aliphatic tertiary amine is that this compound increases the reactivity of the curing reaction to an extra extent while the advantage of an aromatic tertiary amine is that it is much less volatile and is consequently bound better by the cured radiation-curable coating composition.
  • the tertiary amine may contain other functionalities, for example hydroxy, thiol, ether, ester, nitrile, acrylate, vinyl, urethane and amide functionalities.
  • the tertiary amine may also be a monomer, oligomer or polymer with a tertiary amine functionality.
  • An example of a tertiary amine without other functionalities is triethylamine .
  • Examples of tertiary amines with a hydroxy functionality are N,N- dimethyl ethanol amine, N-methyl diethanol amine (Genocure MDEA, RAHN) and triethanol amine.
  • tertiary amine with an ether functionality is N- methylmorpholine.
  • aromatic tertiary amines are 2-ethylhexyl-4-dimethylaminobenzoate (Quantacure
  • oligomer (polymer) tertiary amines are derivatives of the Jeff amines, Actilane 584 (AKCROS) and Actilane 587 (AKCROS) .
  • tertiary amines with a functionality that can co-react during the radiation curing, such as acrylates or vinyl ether functionalities, are Ebecryl P115 (UCB) , Ebecryl 7100 (UCB) , Genomer 5248 (RAHN) , Genomer 8275 (RAHN) , Genomer 5695 (RAHN) , Actilane 705 (AKCROS) , Actilane
  • tertiary amines mentioned above can also be used, as can mixtures of the tertiary amines mentioned above.
  • the amount of tertiary amine used in a radiation-curable coating composition is not critical.
  • the amount of tertiary amine used in a radiation-curable coating composition is between 0.1 and 15 wt.%, relative to the radiation-curable resin composition. With an amount of tertiary amine of less than 0.1 wt. % the reaction rate of the curing reaction decreases substantially. With an amount of tertiary amine of more than 15 wt.% the tertiary amine can no longer be bound entirely in the cured radiation-curable coating composition.
  • the radiation-curable coating composition according to the invention may also contain additives such as pigments, fillers and matting agents.
  • the radiation-curable coating composition may also contain other photoactive compounds.
  • Other photoactive compounds are ketonic and may be aromatic, such as xanthone, thioxanthone and benzophenone .
  • Suitable aromatic ketones are Darocure 1173 (2 -hydroxy-2 -methyl-1- phenylpropane-1-one as the active component) , Irgacure 184 (hydroxy-eyelohexyl phenyl ketone as the active component) , Irgacure 369 (2-benzyl-2-dimethylamino-l- (morpholinophenyl) -butanone-1 as the active component) , acylphosphines such as Lucerine TPO (2,4,6- trimethylbenzoyl diphenyl phosphine oxide) . Chemical derivatives and combinations of these photoinitiators can also be used.
  • xanthone, thioxanthone and benzophenone and their derivatives are employed as photoactive compounds in combination with the maleimide/tertiary amine combination.
  • the radiation-curable coating composition can be cured by different kinds of radiation, such as UV and EB radiation.
  • the most prefered irradiation source is ultraviolet light.
  • Ultraviolet light is preferably high intensity light to provide a dosage to achieve reasonable curing rates .
  • UV-curing equipment we refer to, for example, pages 161-234 of Chemistry and Technology of Uv and EB-formulations, volume 1, Oldring
  • Suitable lamps employed to provide the desired high intensity and availability of wavelength and spectral distribution include for example that available from Fusion systems, Corp.
  • the radiation-curable coating composition according to the invention can be used on different substrates, for example glass, paper, wood, plastic, metals such as aluminium and iron.
  • a 10- ⁇ m-thick film was applied to a gold-coated aluminium plate. This plate was subsequently cured in the infrared machine using a dose of 500 mW/cm 2 and the conversion of the acrylate double bonds was followed.
  • a 10- ⁇ m-thick film was applied to a gold-coated aluminium plate. This plate was subsequently cured in the infrared machine using a dose of 500 mW/cm 2 and the conversion of the acrylate double bonds was followed. A 97 % degree of conversion was obtained after 9.8 seconds.
  • a 10- ⁇ m-thick film was applied to a gold-coated aluminium plate. This plate was subsequently cured in the infrared machine using a dose of 500 mW/cm 2 and the conversion of the acrylate double bonds was followed.
  • a 100- ⁇ m-thick film was applied on a glass plate and subsequently cured with a total dose of 1 J/cm 2 under nitrogen using a Fusion VIP 308 as lamp. After irradiation a cured coating was obtained as indicated with the acetone double rub test . The cured film could withstand 100 acetone double rubs without being affected.
  • a 100- ⁇ m-thick film was applied on a glass plate and subsequently cured with a total dose of 1 J/cm 2 under nitrogen using a Fusion VIP 308 as lamp. After irradiation the coating was not fully cured as indicated with the acetone double rub test. The coating was completely removed from the glassplate after 60 acetone double rubs .
  • a 100- ⁇ m-thick film was applied on a glass plate and subsequently cured with a total dose of 1 J/cm 2 under nitrogen using a Fusion VIP 308 as lamp. After irradiation the coating was not fully cured as indicated with the acetone double rub test . The coating was completely removed from the glassplate after 72 acetone double rubs .
  • Experiment IV and comparative example E as well as Experiment V and comparative example F clearly show that a cured coating is obtained employing the same dose by using the combination of an aliphatic maleimide and a tertiary amine.
  • a 100- ⁇ m-thick film was applied on a glass plate and subsequently cured with a total dose of 1 J/cm 2 under nitrogen using a Fusion VIP 308 as lamp. After irradiation a cured coating was obtained as indicated with the acetone double rub test. The cured film could withstand 100 acetone double rubs without being affected.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention porte sur une composition pour revêtements durcissant sous l'effet de radiations comprenant une résine durcissant sous l'effet de radiations, une maléimide aliphatique, et une amine tertiaire. L'invention porte également sur un substrat en étant entièrement ou partiellement revêtu.
PCT/NL1998/000382 1997-07-18 1998-07-03 Composition pour revetements durcissant sous l'effet de radiations Ceased WO1999003930A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
KR1020007000408A KR20010021844A (ko) 1997-07-18 1998-07-03 방사선-경화성 피복 조성물
CA002297056A CA2297056A1 (fr) 1997-07-18 1998-07-03 Composition pour revetements durcissant sous l'effet de radiations
EP98932622A EP0996680A1 (fr) 1997-07-18 1998-07-03 Composition pour revetements durcissant sous l'effet de radiations
BR9811515-4A BR9811515A (pt) 1997-07-18 1998-07-03 Composição de revestimento curável através de radiação
JP2000503147A JP2001510220A (ja) 1997-07-18 1998-07-03 放射線硬化可能なコーティング組成物
AU82457/98A AU8245798A (en) 1997-07-18 1998-07-03 Radiation-curable coating composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL1006621 1997-07-18
NL1006621A NL1006621C2 (nl) 1997-07-18 1997-07-18 Stralingsuithardbare coatingsamenstelling.

Publications (1)

Publication Number Publication Date
WO1999003930A1 true WO1999003930A1 (fr) 1999-01-28

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL1998/000382 Ceased WO1999003930A1 (fr) 1997-07-18 1998-07-03 Composition pour revetements durcissant sous l'effet de radiations

Country Status (9)

Country Link
EP (1) EP0996680A1 (fr)
JP (1) JP2001510220A (fr)
KR (1) KR20010021844A (fr)
CN (1) CN1264409A (fr)
AU (1) AU8245798A (fr)
BR (1) BR9811515A (fr)
CA (1) CA2297056A1 (fr)
NL (1) NL1006621C2 (fr)
WO (1) WO1999003930A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6555593B1 (en) 1998-01-30 2003-04-29 Albemarle Corporation Photopolymerization compositions including maleimides and processes for using the same
WO2004014970A1 (fr) * 2002-08-08 2004-02-19 3M Innovative Properties Company Composition photodurcissable contenant des derives de la maleide
WO2007030352A2 (fr) 2005-09-07 2007-03-15 Transitions Optical, Inc. Article optique multifocal photochrome
CN100393798C (zh) * 2000-06-19 2008-06-11 东亚合成株式会社 可交联的树脂组合物
US7396861B2 (en) 2004-07-15 2008-07-08 Agfa Graphics Nv Radiation curable compositions
US7507785B2 (en) 2004-07-15 2009-03-24 Agfa Graphics N.V. Polymeric co-initiators
WO2010108862A1 (fr) 2009-03-24 2010-09-30 Basf Se Nouveaux photo-initiateurs oligofonctionnels
US7811480B2 (en) 2004-03-04 2010-10-12 Transitions Optical, Inc. Photochromic optical article
WO2011012560A1 (fr) 2009-07-30 2011-02-03 Basf Se Macrophotoinitiateurs
US9644068B2 (en) 2012-12-18 2017-05-09 Basf Se Semiconducting materials based on naphthalenediimide-vinylene-oligothiophene-vinylene polymers
US9701762B2 (en) 2012-10-19 2017-07-11 Basf Se Hybrid photoinitiators
US9796740B2 (en) 2013-07-08 2017-10-24 Basf Se Liquid bisacylphosphine oxide photoinitiator
EP3459957A1 (fr) 2012-12-19 2019-03-27 IGM Group B.V. Dérivés d'acide bisacylphosphinique, leur préparation et leur utilisation comme photo-initiateurs

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000020517A2 (fr) * 1999-01-19 2000-04-13 Dsm N.V. Compositions durcissables par rayonnements a base de composes de maleimide et procede de production d'un substrat avec une couche durcie

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3855180A (en) * 1971-07-21 1974-12-17 Gen Electric Curable compositions from blend of maleimido compound and vinyl ether
US4025409A (en) * 1975-07-14 1977-05-24 Scm Corporation Dual cure cathodic electrocoating process
JPS5698245A (en) * 1980-01-09 1981-08-07 Mitsubishi Gas Chem Co Inc Curable resin composition
JPH061944A (ja) * 1992-06-19 1994-01-11 Hitachi Chem Co Ltd コーティング用樹脂組成物およびこれを用いたカラーフィルタ保護膜用樹脂組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3855180A (en) * 1971-07-21 1974-12-17 Gen Electric Curable compositions from blend of maleimido compound and vinyl ether
US4025409A (en) * 1975-07-14 1977-05-24 Scm Corporation Dual cure cathodic electrocoating process
JPS5698245A (en) * 1980-01-09 1981-08-07 Mitsubishi Gas Chem Co Inc Curable resin composition
JPH061944A (ja) * 1992-06-19 1994-01-11 Hitachi Chem Co Ltd コーティング用樹脂組成物およびこれを用いたカラーフィルタ保護膜用樹脂組成物

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 005, no. 168 (C - 077) 27 October 1981 (1981-10-27) *
PATENT ABSTRACTS OF JAPAN vol. 018, no. 201 (C - 1188) 8 April 1994 (1994-04-08) *

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6555593B1 (en) 1998-01-30 2003-04-29 Albemarle Corporation Photopolymerization compositions including maleimides and processes for using the same
CN100393798C (zh) * 2000-06-19 2008-06-11 东亚合成株式会社 可交联的树脂组合物
WO2004014970A1 (fr) * 2002-08-08 2004-02-19 3M Innovative Properties Company Composition photodurcissable contenant des derives de la maleide
GB2406572A (en) * 2002-08-08 2005-04-06 3M Innovative Properties Co Photocurable composition containing maleide derivatives
GB2406572B (en) * 2002-08-08 2005-12-14 3M Innovative Properties Co Photocurable composition containing maleimide derivatives
US7811480B2 (en) 2004-03-04 2010-10-12 Transitions Optical, Inc. Photochromic optical article
US7507785B2 (en) 2004-07-15 2009-03-24 Agfa Graphics N.V. Polymeric co-initiators
US7396861B2 (en) 2004-07-15 2008-07-08 Agfa Graphics Nv Radiation curable compositions
WO2007030352A2 (fr) 2005-09-07 2007-03-15 Transitions Optical, Inc. Article optique multifocal photochrome
US7258437B2 (en) 2005-09-07 2007-08-21 Transitions Optical, Inc. Photochromic multifocal optical article
WO2010108862A1 (fr) 2009-03-24 2010-09-30 Basf Se Nouveaux photo-initiateurs oligofonctionnels
WO2011012560A1 (fr) 2009-07-30 2011-02-03 Basf Se Macrophotoinitiateurs
US8906979B2 (en) 2009-07-30 2014-12-09 Basf Se Macrophotoinitiators
US9701762B2 (en) 2012-10-19 2017-07-11 Basf Se Hybrid photoinitiators
US9644068B2 (en) 2012-12-18 2017-05-09 Basf Se Semiconducting materials based on naphthalenediimide-vinylene-oligothiophene-vinylene polymers
EP3459957A1 (fr) 2012-12-19 2019-03-27 IGM Group B.V. Dérivés d'acide bisacylphosphinique, leur préparation et leur utilisation comme photo-initiateurs
US9796740B2 (en) 2013-07-08 2017-10-24 Basf Se Liquid bisacylphosphine oxide photoinitiator

Also Published As

Publication number Publication date
JP2001510220A (ja) 2001-07-31
CA2297056A1 (fr) 1999-01-28
AU8245798A (en) 1999-02-10
BR9811515A (pt) 2000-08-22
NL1006621C2 (nl) 1999-01-19
KR20010021844A (ko) 2001-03-15
EP0996680A1 (fr) 2000-05-03
CN1264409A (zh) 2000-08-23

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