JP4272156B2 - マレイド誘導体を含有する光硬化性組成物 - Google Patents
マレイド誘導体を含有する光硬化性組成物 Download PDFInfo
- Publication number
- JP4272156B2 JP4272156B2 JP2004527574A JP2004527574A JP4272156B2 JP 4272156 B2 JP4272156 B2 JP 4272156B2 JP 2004527574 A JP2004527574 A JP 2004527574A JP 2004527574 A JP2004527574 A JP 2004527574A JP 4272156 B2 JP4272156 B2 JP 4272156B2
- Authority
- JP
- Japan
- Prior art keywords
- photocurable composition
- maleimide
- acrylate
- meth
- acylphosphine oxide
- 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.)
- Expired - Fee Related
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- 239000000203 mixture Substances 0.000 title claims description 56
- 239000000463 material Substances 0.000 claims description 32
- 150000008366 benzophenones Chemical class 0.000 claims description 27
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- 125000000962 organic group Chemical group 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 37
- 239000000976 ink Substances 0.000 description 24
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- 238000000576 coating method Methods 0.000 description 12
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- 239000003086 colorant Substances 0.000 description 10
- 230000005855 radiation Effects 0.000 description 9
- 238000007639 printing Methods 0.000 description 8
- 239000000049 pigment Substances 0.000 description 7
- 229920003192 poly(bis maleimide) Polymers 0.000 description 7
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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- 230000000052 comparative effect Effects 0.000 description 6
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- 125000004432 carbon atom Chemical group C* 0.000 description 4
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
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- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 3
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- 210000003813 thumb Anatomy 0.000 description 3
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- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- GRDGBWVSVMLKBV-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl GRDGBWVSVMLKBV-UHFFFAOYSA-N 0.000 description 1
- OJLABXSUFRIXFL-UHFFFAOYSA-N (2-benzoylphenyl)-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C(=O)C1=CC=CC=C1 OJLABXSUFRIXFL-UHFFFAOYSA-N 0.000 description 1
- ABEVIHIQUUXDMS-UHFFFAOYSA-N (2-bromophenyl)-phenylmethanone Chemical compound BrC1=CC=CC=C1C(=O)C1=CC=CC=C1 ABEVIHIQUUXDMS-UHFFFAOYSA-N 0.000 description 1
- OJFZCPMENWLPRI-UHFFFAOYSA-N (2-ethylphenyl)-phenylmethanone Chemical compound CCC1=CC=CC=C1C(=O)C1=CC=CC=C1 OJFZCPMENWLPRI-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- 0 **(C(C=C1)=O)C1=[U] Chemical compound **(C(C=C1)=O)C1=[U] 0.000 description 1
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- QYOJZFBQEAZNEW-UHFFFAOYSA-N 1-(2-methylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC=C1N1C(=O)C=CC1=O QYOJZFBQEAZNEW-UHFFFAOYSA-N 0.000 description 1
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- RFVHVYKVRGKLNK-UHFFFAOYSA-N bis(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1 RFVHVYKVRGKLNK-UHFFFAOYSA-N 0.000 description 1
- ZWPWLKXZYNXATK-UHFFFAOYSA-N bis(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(C)C=C1 ZWPWLKXZYNXATK-UHFFFAOYSA-N 0.000 description 1
- BSILAEQTGTZMIW-UHFFFAOYSA-N bis(4-phenoxyphenyl)methanone Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 BSILAEQTGTZMIW-UHFFFAOYSA-N 0.000 description 1
- QRQHCGWCUVLPSQ-UHFFFAOYSA-N bis(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 QRQHCGWCUVLPSQ-UHFFFAOYSA-N 0.000 description 1
- CDSXFEKYNHFZGM-UHFFFAOYSA-N bis[2-(2,5-dioxopyrrol-1-yl)ethyl] carbonate Chemical compound O=C1C=CC(=O)N1CCOC(=O)OCCN1C(=O)C=CC1=O CDSXFEKYNHFZGM-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- AOIISAGZKQIFKC-UHFFFAOYSA-N ethyl carbamate 1-ethylpyrrole-2,5-dione 3,5,5-trimethylcyclohex-2-en-1-one Chemical compound C(C)N1C(C=CC1=O)=O.C(C)N1C(C=CC1=O)=O.NC(=O)OCC.NC(=O)OCC.O=C1C=C(CC(C)(C)C1)C AOIISAGZKQIFKC-UHFFFAOYSA-N 0.000 description 1
- JZMPIUODFXBXSC-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.CCOC(N)=O JZMPIUODFXBXSC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010316 high energy milling Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Classifications
-
- 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
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/36—Amides or imides
- C08F22/40—Imides, e.g. cyclic imides
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Paints Or Removers (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/214,619 US20040029044A1 (en) | 2002-08-08 | 2002-08-08 | Photocurable composition |
| PCT/US2003/019136 WO2004014970A1 (en) | 2002-08-08 | 2003-06-17 | Photocurable composition containing maleide derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005535745A JP2005535745A (ja) | 2005-11-24 |
| JP2005535745A5 JP2005535745A5 (enExample) | 2006-07-20 |
| JP4272156B2 true JP4272156B2 (ja) | 2009-06-03 |
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| JP2004527574A Expired - Fee Related JP4272156B2 (ja) | 2002-08-08 | 2003-06-17 | マレイド誘導体を含有する光硬化性組成物 |
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| US (1) | US20040029044A1 (enExample) |
| JP (1) | JP4272156B2 (enExample) |
| KR (1) | KR101009124B1 (enExample) |
| CN (1) | CN1307221C (enExample) |
| AU (1) | AU2003282345A1 (enExample) |
| DE (1) | DE10393025T5 (enExample) |
| GB (1) | GB2406572B (enExample) |
| WO (1) | WO2004014970A1 (enExample) |
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| US9138383B1 (en) * | 2004-04-28 | 2015-09-22 | The Regents Of The University Of Colorado, A Body Corporate | Nanogel materials and methods of use thereof |
| JP4559892B2 (ja) * | 2005-03-28 | 2010-10-13 | 太陽インキ製造株式会社 | 着色感光性樹脂組成物及びその硬化物 |
| US20080233307A1 (en) * | 2007-02-09 | 2008-09-25 | Chisso Corporation | Photocurable inkjet ink |
| KR100942369B1 (ko) * | 2007-04-12 | 2010-02-12 | 주식회사 엘지화학 | 경화성 수지 제조용 조성물, 이에 의해 제조된 경화성수지, 및 이를 포함하는 잉크 조성물 |
| US7547105B2 (en) * | 2007-07-16 | 2009-06-16 | 3M Innovative Properties Company | Prismatic retroreflective article with cross-linked image layer and method of making same |
| US20100055423A1 (en) * | 2008-09-04 | 2010-03-04 | Xerox Corporation | Machine Readable Code Comprising Ultra-Violet Curable Gellant Inks |
| JP2012511178A (ja) * | 2008-12-08 | 2012-05-17 | スリーエム イノベイティブ プロパティズ カンパニー | 図形を有する保護オーバーレイ及びオーバーレイを含む再帰反射性物品 |
| CA2745761A1 (en) * | 2008-12-08 | 2010-07-08 | 3M Innovative Properties Company | Prismatic retroreflective article bearing a graphic and method of making same |
| JP2010214636A (ja) * | 2009-03-13 | 2010-09-30 | E I Du Pont De Nemours & Co | 光学的読み取り情報を備える印刷物 |
| US20130025495A1 (en) * | 2010-01-11 | 2013-01-31 | Isp Investments Inc. | Compositions comprising a reactive monomer and uses thereof |
| US8628679B2 (en) * | 2010-01-20 | 2014-01-14 | Phoenix Inks And Coatings, Llc | High-definition demetalization process |
| JP5615600B2 (ja) | 2010-06-09 | 2014-10-29 | 富士フイルム株式会社 | インクジェット記録用インク組成物、インクジェット記録方法及びインクジェット印画物 |
| DK2588549T3 (en) * | 2010-06-30 | 2015-01-12 | Dsm Ip Assets Bv | D1479-STABLE LIQUID BAP photoinitiator AND ITS USE IN radiation-FORMATIONS |
| ES2550469T3 (es) * | 2010-12-20 | 2015-11-10 | Agfa Graphics N.V. | Método para fabricar una matriz de impresión flexográfica |
| EP2656145B1 (en) | 2010-12-20 | 2019-03-20 | Agfa Nv | A curable jettable fluid for making a flexographic printing master |
| JP5821225B2 (ja) * | 2011-03-15 | 2015-11-24 | コニカミノルタ株式会社 | 活性エネルギー線硬化型インクジェットインク組成物、及びインクジェット記録方法 |
| JP5398760B2 (ja) * | 2011-02-23 | 2014-01-29 | 富士フイルム株式会社 | インク組成物、画像形成方法及び印画物 |
| JP5920346B2 (ja) * | 2011-06-17 | 2016-05-18 | コニカミノルタ株式会社 | 光硬化性インクジェットインク |
| JP5857710B2 (ja) * | 2011-12-14 | 2016-02-10 | コニカミノルタ株式会社 | 活性エネルギー線硬化型インクジェットインク、およびそれを用いるインクジェット記録方法 |
| JP5825089B2 (ja) * | 2011-12-21 | 2015-12-02 | コニカミノルタ株式会社 | 紫外線硬化型非水系インクジェットインク |
| EP2945755B1 (en) | 2013-02-06 | 2019-09-11 | Sun Chemical Corporation | Digital printing inks |
| JP6808746B2 (ja) | 2016-02-19 | 2021-01-06 | アベリー・デニソン・コーポレイションＡｖｅｒｙ Ｄｅｎｎｉｓｏｎ Ｃｏｒｐｏｒａｔｉｏｎ | 接着剤を製造する２段階の方法及び関連組成物 |
| US11161995B2 (en) | 2016-07-11 | 2021-11-02 | Soreq Nuclear Research Center | Bismaleimide-based solution for inkjet ink for three dimensional printing |
| EP4790115A2 (en) | 2016-10-25 | 2026-08-12 | Avery Dennison Corporation | Block polymers with photoinitiator groups in backbone and their use in adhesive compositions |
| WO2018212116A1 (ja) * | 2017-05-15 | 2018-11-22 | 三菱瓦斯化学株式会社 | リソグラフィー用膜形成材料、リソグラフィー用膜形成用組成物、リソグラフィー用下層膜及びパターン形成方法 |
| GB2562747B (en) | 2017-05-23 | 2019-06-26 | Henkel IP & Holding GmbH | Low-viscosity photocurable adhesive compositions |
| JP7507088B2 (ja) | 2017-12-19 | 2024-06-27 | エイブリィ・デニソン・コーポレイション | ペンダント官能基の後重合官能化 |
| EP3842863A4 (en) * | 2018-08-20 | 2021-11-03 | Mitsubishi Gas Chemical Company, Inc. | FILM EDUCATION MATERIAL FOR LITHOGRAPHY, COMPOSITION FOR FILM FORMATION FOR LITHOGRAPHY, LAYER FILM FOR LITHOGRAPHY AND PATTERN GENERATION PROCESS |
| JP7212301B2 (ja) * | 2018-08-30 | 2023-01-25 | 三菱瓦斯化学株式会社 | 樹脂組成物、樹脂シート、多層プリント配線板及び半導体装置 |
| KR102192274B1 (ko) * | 2018-08-30 | 2020-12-17 | 미츠비시 가스 가가쿠 가부시키가이샤 | 수지 조성물, 수지 시트, 다층 프린트 배선판, 및 반도체 장치 |
| EP3632941B1 (en) * | 2018-10-01 | 2023-08-23 | Cubicure GmbH | Resin composition |
| US11345772B2 (en) * | 2019-09-06 | 2022-05-31 | Canon Kabushiki Kaisha | Curable composition |
| JP7676107B2 (ja) * | 2019-11-19 | 2025-05-14 | スリーエム イノベイティブ プロパティズ カンパニー | 放射線硬化型インクジェットインク、装飾シート及び装飾シートの製造方法 |
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| JP4014803B2 (ja) * | 1997-08-05 | 2007-11-28 | セリコル、リミテッド | インクジェットインク |
| ATE333114T1 (de) * | 1998-01-30 | 2006-08-15 | Albemarle Corp | Maleimide enthaltende fotopolymerisierbare zusammensetzungen und verfahren zu deren verwendung |
| US6180228B1 (en) * | 1998-03-02 | 2001-01-30 | 3M Innovative Properties Company | Outdoor advertising system |
| US6312123B1 (en) * | 1998-05-01 | 2001-11-06 | L&P Property Management Company | Method and apparatus for UV ink jet printing on fabric and combination printing and quilting thereby |
| US6200647B1 (en) * | 1998-07-02 | 2001-03-13 | 3M Innovative Properties Company | Image receptor medium |
| DE69930948T2 (de) * | 1998-09-28 | 2006-09-07 | Kimberly-Clark Worldwide, Inc., Neenah | Chelate mit chinoiden gruppen als photoinitiatoren |
| US6139920A (en) * | 1998-12-21 | 2000-10-31 | Xerox Corporation | Photoresist compositions |
| AU2331600A (en) * | 1999-01-19 | 2000-04-26 | Dsm N.V. | Radiation-curable compositions comprising maleimide compounds and method for producing a substrate with a cured layer |
| US6726317B2 (en) * | 1999-09-03 | 2004-04-27 | L&P Property Management Company | Method and apparatus for ink jet printing |
| JP2002121221A (ja) * | 2000-08-09 | 2002-04-23 | Dainippon Ink & Chem Inc | 光硬化性着色組成物 |
| JP2002161106A (ja) * | 2000-09-13 | 2002-06-04 | Dainippon Ink & Chem Inc | 光硬化性着色組成物 |
| MXPA03003997A (es) * | 2000-11-09 | 2004-02-12 | 3M Innovative Properties Co | Composiciones fluidas de tinta, eyectables, curables por radiacion, resistentes a la intemperie, particularmente adecuadas para aplicaciones exteriores. |
| US6595615B2 (en) * | 2001-01-02 | 2003-07-22 | 3M Innovative Properties Company | Method and apparatus for selection of inkjet printing parameters |
-
2002
- 2002-08-08 US US10/214,619 patent/US20040029044A1/en not_active Abandoned
-
2003
- 2003-06-17 DE DE10393025T patent/DE10393025T5/de not_active Ceased
- 2003-06-17 WO PCT/US2003/019136 patent/WO2004014970A1/en not_active Ceased
- 2003-06-17 AU AU2003282345A patent/AU2003282345A1/en not_active Abandoned
- 2003-06-17 CN CNB038189046A patent/CN1307221C/zh not_active Expired - Fee Related
- 2003-06-17 JP JP2004527574A patent/JP4272156B2/ja not_active Expired - Fee Related
- 2003-06-17 KR KR1020057002239A patent/KR101009124B1/ko not_active Expired - Fee Related
- 2003-06-17 GB GB0500794A patent/GB2406572B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB2406572B (en) | 2005-12-14 |
| AU2003282345A1 (en) | 2004-02-25 |
| KR20050095578A (ko) | 2005-09-29 |
| GB2406572A (en) | 2005-04-06 |
| DE10393025T5 (de) | 2005-08-25 |
| JP2005535745A (ja) | 2005-11-24 |
| GB0500794D0 (en) | 2005-02-23 |
| KR101009124B1 (ko) | 2011-01-18 |
| WO2004014970A1 (en) | 2004-02-19 |
| US20040029044A1 (en) | 2004-02-12 |
| CN1675270A (zh) | 2005-09-28 |
| CN1307221C (zh) | 2007-03-28 |
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