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 (https=) | 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 (https=) |
| JP (1) | JP4272156B2 (https=) |
| KR (1) | KR101009124B1 (https=) |
| CN (1) | CN1307221C (https=) |
| AU (1) | AU2003282345A1 (https=) |
| DE (1) | DE10393025T5 (https=) |
| GB (1) | GB2406572B (https=) |
| WO (1) | WO2004014970A1 (https=) |
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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 |
| CN101652419B (zh) * | 2007-04-12 | 2013-04-24 | Lg化学株式会社 | 用于制备固化树脂的组合物、由该组合物制备的固化树脂和包含该树脂的墨水组合物 |
| 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 |
| CN102272638B (zh) * | 2008-12-08 | 2014-04-30 | 3M创新有限公司 | 具有图形的防护覆盖物以及包括该覆盖物的逆向反射制品 |
| KR101610427B1 (ko) * | 2008-12-08 | 2016-04-07 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 그래픽을 갖는 프리즘형 재귀반사성 물품 및 이를 제조하는 방법 |
| 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 |
| US9062082B2 (en) * | 2010-06-30 | 2015-06-23 | Dsm Ip Assets B.V. | D1479 stable liquid BAP photoinitiator and its use in radiation curable compositions |
| US9309341B2 (en) | 2010-12-20 | 2016-04-12 | Agfa Graphics Nv | Curable jettable fluid for making a flexographic printing master |
| ES2550469T3 (es) * | 2010-12-20 | 2015-11-10 | Agfa Graphics N.V. | Método para fabricar una matriz de impresión flexográfica |
| 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 |
| US10414953B2 (en) | 2016-02-19 | 2019-09-17 | Avery Dennison Corporation | Two stage methods for processing adhesives and related compositions |
| WO2018011674A1 (en) * | 2016-07-11 | 2018-01-18 | Soreq Nuclear Research Center | Bismaleimide-based solution for inkjet ink for three dimensional printing |
| CN110099939B (zh) | 2016-10-25 | 2022-09-06 | 艾利丹尼森公司 | 在主链中具有光引发剂基团的嵌段聚合物及其用于粘合剂组合物中的用途 |
| JP7054459B2 (ja) * | 2017-05-15 | 2022-04-14 | 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 |
| AU2018392478B2 (en) | 2017-12-19 | 2023-03-16 | Avery Dennison Corporation | Post-polymerization functionalization of pendant functional groups |
| KR20210045357A (ko) * | 2018-08-20 | 2021-04-26 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 리소그래피용 막형성재료, 리소그래피용 막형성용 조성물, 리소그래피용 하층막 및 패턴 형성방법 |
| 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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| GB9516108D0 (en) * | 1995-08-05 | 1995-10-04 | Tioxide Specialties Ltd | Printing inks |
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| US6030703A (en) * | 1997-08-13 | 2000-02-29 | Sartomer Company, Inc. | Radiation curable compositions comprising an unsaturated polyester and a compound having two to six-propenyl ether groups |
| 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 |
| CA2353685A1 (en) * | 1998-09-28 | 2000-04-06 | Kimberly-Clark Worldwide, Inc. | Chelates comprising chinoid groups as photoinitiators |
| 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 |
| WO2002038688A2 (en) * | 2000-11-09 | 2002-05-16 | 3M Innovative Properties Company | Weather resistant, ink jettable, radiation curable, fluid compositions particularly suitable for outdoor applications |
| 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 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
- 2003-06-17 DE DE10393025T patent/DE10393025T5/de not_active Ceased
- 2003-06-17 AU AU2003282345A patent/AU2003282345A1/en not_active Abandoned
- 2003-06-17 WO PCT/US2003/019136 patent/WO2004014970A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005535745A (ja) | 2005-11-24 |
| GB2406572B (en) | 2005-12-14 |
| CN1307221C (zh) | 2007-03-28 |
| AU2003282345A1 (en) | 2004-02-25 |
| DE10393025T5 (de) | 2005-08-25 |
| GB2406572A (en) | 2005-04-06 |
| US20040029044A1 (en) | 2004-02-12 |
| WO2004014970A1 (en) | 2004-02-19 |
| KR20050095578A (ko) | 2005-09-29 |
| CN1675270A (zh) | 2005-09-28 |
| KR101009124B1 (ko) | 2011-01-18 |
| GB0500794D0 (en) | 2005-02-23 |
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