FI89162B - Kopolymeriserbara fotoinitiatorer - Google Patents
Kopolymeriserbara fotoinitiatorer Download PDFInfo
- Publication number
- FI89162B FI89162B FI863894A FI863894A FI89162B FI 89162 B FI89162 B FI 89162B FI 863894 A FI863894 A FI 863894A FI 863894 A FI863894 A FI 863894A FI 89162 B FI89162 B FI 89162B
- Authority
- FI
- Finland
- Prior art keywords
- photoinitiators
- compounds
- formula
- phenyl
- photopolymerization
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000976 ink Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 101001077374 Oryza sativa subsp. japonica UMP-CMP kinase 3 Proteins 0.000 claims 1
- 239000003999 initiator Substances 0.000 description 43
- -1 benzoin ethers Chemical class 0.000 description 30
- 238000000576 coating method Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 230000005855 radiation Effects 0.000 description 10
- 238000001723 curing Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 8
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 235000019589 hardness Nutrition 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 238000003848 UV Light-Curing Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YLQFBBDMNWYTOS-UHFFFAOYSA-N [4-[2,4-dihydroxy-2,4-dimethyl-3-oxo-5-(4-prop-2-enoyloxyphenyl)pentyl]phenyl] prop-2-enoate Chemical compound C(C=C)(=O)OC1=CC=C(C=C1)CC(C)(O)C(=O)C(C)(CC1=CC=C(C=C1)OC(C=C)=O)O YLQFBBDMNWYTOS-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000009965 odorless effect Effects 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 150000008366 benzophenones Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- PREGASFGSUVSBQ-UHFFFAOYSA-N (2,4-dimethyl-3-oxo-1,5-diphenyl-4-prop-2-enoyloxypentan-2-yl) prop-2-enoate Chemical compound C1(=CC=CC=C1)CC(C)(OC(C=C)=O)C(=O)C(C)(CC1=CC=CC=C1)OC(C=C)=O PREGASFGSUVSBQ-UHFFFAOYSA-N 0.000 description 2
- WAGRIKSHWXFXHV-UHFFFAOYSA-N 1-hydroxybutyl prop-2-enoate Chemical compound CCCC(O)OC(=O)C=C WAGRIKSHWXFXHV-UHFFFAOYSA-N 0.000 description 2
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 2
- NDJCDNQKIINPMP-UHFFFAOYSA-N 2,4-dihydroxy-2,4-dimethyl-1,5-diphenylpentan-3-one Chemical compound C=1C=CC=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=CC=C1 NDJCDNQKIINPMP-UHFFFAOYSA-N 0.000 description 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 2
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- SGJPFMDBSWNEDP-UHFFFAOYSA-N [4-[2,4-dihydroxy-2,4-dimethyl-5-[4-(2-methylprop-2-enoyloxy)phenyl]-3-oxopentyl]phenyl] 2-methylprop-2-enoate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1CC(C)(O)C(=O)C(C)(O)CC1=CC=C(OC(=O)C(C)=C)C=C1 SGJPFMDBSWNEDP-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- OMWSZDODENFLSV-UHFFFAOYSA-N (5-chloro-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 OMWSZDODENFLSV-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- UTHDGOQKIWLLCO-UHFFFAOYSA-N 1-hydroxyhexyl prop-2-enoate Chemical compound CCCCCC(O)OC(=O)C=C UTHDGOQKIWLLCO-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- BUFQATNYFCBSNB-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis(4-hydroxyphenyl)-2,4-dimethylpentan-3-one Chemical compound C=1C=C(O)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(O)C=C1 BUFQATNYFCBSNB-UHFFFAOYSA-N 0.000 description 1
- JHYHYSDFWREWFU-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethyl)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(CCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(CCO)C=C1 JHYHYSDFWREWFU-UHFFFAOYSA-N 0.000 description 1
- IFOWXFUNZNAQJJ-UHFFFAOYSA-N 2,4-dihydroxy-2,4-dimethylpentan-3-one Chemical compound CC(C)(O)C(=O)C(C)(C)O IFOWXFUNZNAQJJ-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- FLKIJNISGLPWAC-UHFFFAOYSA-N 2-[4-(2-methylpropanoyl)phenoxy]ethyl acetate Chemical compound CC(C)C(=O)C1=CC=C(OCCOC(C)=O)C=C1 FLKIJNISGLPWAC-UHFFFAOYSA-N 0.000 description 1
- XNLHQURWXIWCDF-UHFFFAOYSA-N 2-[4-[2,4-dihydroxy-2,4-dimethyl-3-oxo-5-[4-(2-prop-2-enoyloxyethoxy)phenyl]pentyl]phenoxy]ethyl prop-2-enoate Chemical compound C=1C=C(OCCOC(=O)C=C)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCOC(=O)C=C)C=C1 XNLHQURWXIWCDF-UHFFFAOYSA-N 0.000 description 1
- DLPLWDAGOAVZNB-UHFFFAOYSA-N 2-[4-[2,4-dihydroxy-2,4-dimethyl-3-oxo-5-[4-(2-prop-2-enoyloxyethylsulfanyl)phenyl]pentyl]phenyl]sulfanylethyl prop-2-enoate Chemical compound C(C=C)(=O)OCCSC1=CC=C(C=C1)CC(C)(O)C(=O)C(C)(CC1=CC=C(C=C1)SCCOC(C=C)=O)O DLPLWDAGOAVZNB-UHFFFAOYSA-N 0.000 description 1
- PEVGZCHVOHFKLB-UHFFFAOYSA-N 2-[4-[2,4-dihydroxy-2,4-dimethyl-5-[4-[2-(2-methylprop-2-enoyloxy)ethoxy]phenyl]-3-oxopentyl]phenoxy]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(OCCOC(=O)C(=C)C)=CC=C1CC(C)(O)C(=O)C(C)(O)CC1=CC=C(OCCOC(=O)C(C)=C)C=C1 PEVGZCHVOHFKLB-UHFFFAOYSA-N 0.000 description 1
- QSIZPRQVKWCGES-UHFFFAOYSA-N 2-[4-[2,4-dimethyl-3-oxo-2,4-di(prop-2-enoyloxy)-5-[4-(2-prop-2-enoyloxyethoxy)phenyl]pentyl]phenoxy]ethyl prop-2-enoate Chemical compound C(C=C)(=O)OCCOC1=CC=C(C=C1)CC(C)(OC(C=C)=O)C(=O)C(C)(CC1=CC=C(C=C1)OCCOC(C=C)=O)OC(C=C)=O QSIZPRQVKWCGES-UHFFFAOYSA-N 0.000 description 1
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 1
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- QBQUAVQKVLSWMY-UHFFFAOYSA-N 2-hydroxy-1,2-diphenylethanone;prop-2-enoic acid Chemical class OC(=O)C=C.C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 QBQUAVQKVLSWMY-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- WHFKYDMBUMLWDA-UHFFFAOYSA-N 2-phenoxyethyl acetate Chemical compound CC(=O)OCCOC1=CC=CC=C1 WHFKYDMBUMLWDA-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- BZISNWGGPWSXTK-UHFFFAOYSA-N 3-hydroxypropyl benzoate Chemical compound OCCCOC(=O)C1=CC=CC=C1 BZISNWGGPWSXTK-UHFFFAOYSA-N 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- 229920002545 silicone oil Polymers 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
- HERSKCAGZCXYMC-UHFFFAOYSA-N thiophen-3-ol Chemical compound OC=1C=CSC=1 HERSKCAGZCXYMC-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
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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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- 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
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Wood Science & Technology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
Claims (9)
1. Förening med den allmänna formeln li 25 89 1 62
4. Användning enligt patentkravet 3 i med hjälp av UV-ljus härdbara tryckfärgar.
5. Användning enligt patentkravet 3 för härdning av vattenhaltiga prepolymerdispersioner genom besträl- 5 ning.
6. Förfarande för fotopolymerisering av ety-leniskt omättade föreningar eller system som innehäller dessa, kännetecknat därav, att tili blandnin-gen som skall polymeriseras tillsätts före början av 10 fotopolymerisering ätminstone en förening med formeln I som kopolymeriserbar fotoinitiator.
7. Förfarande enligt patentkravet 6, kännetecknat därav, att tili blandningen som skall polymeriseras tillsätts före början av fotopolymerisering 15 0,1 - 20 vikt-% av föreningen med formeln I.
8. Fotopolymeriserbart system som innehäller ätminstone en etyleniskt omättad, fotopolymeriserbar förening och eventuellt andra kända och vanliga tillsats-ämnen, kännetecknat därav, att det innehäller 20 ätminstone en förening med formeln I som kopolymeriserbar fotoinitiator.
9. Fotopolymeriserbart system enligt patentkravet 8, kännetecknat därav, att det innehäller 0,1 - 20 vikt-% av föreningen med formeln I.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3534645 | 1985-09-28 | ||
| DE19853534645 DE3534645A1 (de) | 1985-09-28 | 1985-09-28 | Copolymerisierbare fotoinitiatoren |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI863894A0 FI863894A0 (fi) | 1986-09-26 |
| FI863894A FI863894A (fi) | 1987-03-29 |
| FI89162B true FI89162B (fi) | 1993-05-14 |
| FI89162C FI89162C (sv) | 1993-08-25 |
Family
ID=6282204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI863894A FI89162C (sv) | 1985-09-28 | 1986-09-26 | Kopolymeriserbara fotoinitiatorer |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4922004A (sv) |
| EP (1) | EP0217205B1 (sv) |
| JP (1) | JP2514804B2 (sv) |
| AR (1) | AR241265A1 (sv) |
| AT (1) | ATE70258T1 (sv) |
| AU (1) | AU595830B2 (sv) |
| BR (1) | BR8604672A (sv) |
| CA (1) | CA1275109A (sv) |
| CS (1) | CS257798B2 (sv) |
| DD (1) | DD258614A5 (sv) |
| DE (2) | DE3534645A1 (sv) |
| DK (1) | DK172255B1 (sv) |
| ES (1) | ES2004660A6 (sv) |
| FI (1) | FI89162C (sv) |
| HU (1) | HU201510B (sv) |
| PL (1) | PL149572B2 (sv) |
| ZA (1) | ZA867370B (sv) |
Families Citing this family (169)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3738567A1 (de) * | 1987-03-12 | 1988-09-22 | Merck Patent Gmbh | Coreaktive fotoinitiatoren |
| EP0302831B1 (en) * | 1987-08-05 | 1993-05-12 | Ciba-Geigy Ag | Compounds |
| US5095044A (en) * | 1987-08-27 | 1992-03-10 | Ciba-Geigy Corporation | Oligomeric benzil ketals and their use as photoinitiators |
| US4950795A (en) * | 1987-08-27 | 1990-08-21 | Ciba-Geigy Corporation | Oligomeric benzil ketals and their use as photoinitiators |
| US5248805A (en) * | 1988-12-31 | 1993-09-28 | Basf Aktiengesellschaft | Radiation-senstive, ethylenically unsaturated, copolymerizable compounds and their preparation |
| US5118779A (en) * | 1989-10-10 | 1992-06-02 | Polymedica Industries, Inc. | Hydrophilic polyurethane elastomers |
| DE4014489A1 (de) * | 1990-05-07 | 1991-11-14 | Merck Patent Gmbh | Copolymerisierbare benzilketal-fotoinitiatoren |
| RU2091385C1 (ru) * | 1991-09-23 | 1997-09-27 | Циба-Гейги АГ | Бисацилфосфиноксиды, состав и способ нанесения покрытий |
| IL101993A (en) * | 1991-10-23 | 1995-06-29 | Hughes Aircraft Co | Method for creating enhanced liquid crystal membranes with diffused polymer with initiating photo that can be copolymerized |
| ES2037611B1 (es) * | 1991-12-04 | 1994-04-01 | Consejo Superior Investigacion | Nuevos modelos, monomeros y polimeros fotosensibles y portadores del grupo-p-nitronaftil-aminocarbonilo. su procedimiento de preparacion. |
| US5274179A (en) * | 1993-04-06 | 1993-12-28 | Alliedsignal Inc. | Fluorinated photoinitiators and their application in UV curing of fluorinated monomers |
| USRE35060E (en) * | 1991-12-11 | 1995-10-10 | Alliedsignal Inc. | Fluorinated photoinitiators and their application in UV curing of fluorinated monomers |
| ES2059261B1 (es) * | 1992-10-08 | 1995-11-16 | Ciba Geigy Ag | Alquil-bisacilfosfinoxidos. |
| US5506279A (en) * | 1993-10-13 | 1996-04-09 | Minnesota Mining And Manufacturing Company | Acrylamido functional disubstituted acetyl aryl ketone photoinitiators |
| DE69520434T2 (de) * | 1994-07-29 | 2001-10-18 | Minnesota Mining & Mfg | Acrylischer sirup, welcher durch härtung in ein vernetztes viscoelastisches material überführbar ist |
| WO1996035725A1 (en) * | 1995-05-10 | 1996-11-14 | Avery Dennison Corporation | Pigmented, uv-cured, acrylic-based, pressure sensitive adhesives, and method for making same |
| JPH11509329A (ja) * | 1995-07-19 | 1999-08-17 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 不均質光開始剤、光重合性組成物およびその使用 |
| EP0869977A1 (en) * | 1995-12-29 | 1998-10-14 | Minnesota Mining And Manufacturing Company | Use of pendant photoreactive moieties on polymer precursors to prepare hydrophilic pressure sensitive adhesives |
| DE19625753C2 (de) * | 1996-06-27 | 2000-05-18 | Basf Coatings Ag | Holzbeschichtungsfolie |
| GB2352718A (en) | 1999-08-04 | 2001-02-07 | Coates Brothers Plc | Photoinitiators |
| ATE409708T1 (de) * | 2000-12-13 | 2008-10-15 | Ciba Holding Inc | Oberflächenaktive photoinitiatoren |
| CN101508883B (zh) * | 2001-05-16 | 2012-11-07 | 积水化学工业株式会社 | 固化树脂组合物及用于显示器的密封剂和封端材料 |
| US7253131B2 (en) * | 2001-05-16 | 2007-08-07 | Sekisui Chemical Co., Ltd. | Curing resin composition and sealants and end-sealing materials for displays |
| EP1401899B1 (en) | 2001-06-08 | 2009-08-26 | Basf Se | Water soluble radiation activatable polymer resins |
| JP4291638B2 (ja) | 2003-07-29 | 2009-07-08 | 富士フイルム株式会社 | アルカリ可溶性ポリマー及びそれを用いた平版印刷版原版 |
| EP1504772A1 (en) * | 2003-08-06 | 2005-02-09 | The Procter & Gamble Company | Superabsorbent polymers having radiation activable surface cross-linkers and method of making them |
| US20050065227A1 (en) * | 2003-09-22 | 2005-03-24 | Condon John R. | Visible-light sensitive macro-initiator |
| US8080705B2 (en) * | 2004-07-28 | 2011-12-20 | The Procter & Gamble Company | Superabsorbent polymers comprising direct covalent bonds between polymer chain segments and method of making them |
| EP1624002B1 (en) * | 2004-08-07 | 2019-04-03 | The Procter & Gamble Company | Superabsorbent polymer particles comprising functionalizers and method of making them |
| JP5089866B2 (ja) | 2004-09-10 | 2012-12-05 | 富士フイルム株式会社 | 平版印刷方法 |
| EP1669394A1 (en) * | 2004-12-10 | 2006-06-14 | The Procter & Gamble Company | Superabsorbent polymer particles with improved surface cross-linking and hydrophilicity and method of making them |
| US20060128827A1 (en) * | 2004-12-10 | 2006-06-15 | The Procter & Gamble Company | Absorbent members comprising modified water absorbent resin for use in diapers |
| JP5421533B2 (ja) | 2004-12-22 | 2014-02-19 | チバ ホールディング インコーポレーテッド | 強接着性コーティングの製造方法 |
| JP4967378B2 (ja) * | 2005-03-29 | 2012-07-04 | セイコーエプソン株式会社 | インク組成物 |
| JP4474317B2 (ja) | 2005-03-31 | 2010-06-02 | 富士フイルム株式会社 | 平版印刷版の作製方法 |
| JP2006335826A (ja) | 2005-05-31 | 2006-12-14 | Fujifilm Holdings Corp | インクジェット記録用インク組成物およびこれを用いた平版印刷版の作製方法 |
| JP2007077366A (ja) * | 2005-09-16 | 2007-03-29 | Procter & Gamble Co | 吸水剤の製法 |
| JP5220279B2 (ja) * | 2006-03-23 | 2013-06-26 | 古河電気工業株式会社 | 光ファイバ素線 |
| WO2007120561A2 (en) * | 2006-04-10 | 2007-10-25 | The Procter & Gamble Company | An absorbent member comprising a modified water absorbent resin |
| JP5276264B2 (ja) | 2006-07-03 | 2013-08-28 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、及び、平版印刷版の製造方法 |
| JP2009541554A (ja) * | 2006-07-04 | 2009-11-26 | チバ ホールディング インコーポレーテッド | 異相重合技術によって作製された光開始剤の水ベースの濃縮されたプロダクト形態 |
| US20080132599A1 (en) | 2006-11-30 | 2008-06-05 | Seiko Epson Corporation. | Ink composition, two-pack curing ink composition set, and recording method and recorded matter using these |
| JP5507256B2 (ja) * | 2006-12-13 | 2014-05-28 | スリーエム イノベイティブ プロパティズ カンパニー | 酸性成分及び光退色性染料を有する歯科用組成物の使用方法 |
| JP5472670B2 (ja) | 2007-01-29 | 2014-04-16 | セイコーエプソン株式会社 | インクセット、インクジェット記録方法及び記録物 |
| US8541063B2 (en) | 2007-02-06 | 2013-09-24 | Fujifilm Corporation | Undercoat solution, ink-jet recording method and ink-jet recording device |
| EP1955850B1 (en) | 2007-02-07 | 2011-04-20 | FUJIFILM Corporation | Ink-jet recording device having ink-jet head maintenance device and ink-jet head maintenance method |
| EP2121049B1 (en) | 2007-02-22 | 2016-03-30 | The Procter and Gamble Company | Method of surface treating particulate material using electromagnetic radiation |
| JP5227521B2 (ja) | 2007-02-26 | 2013-07-03 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、及び、インクセット |
| US8894197B2 (en) | 2007-03-01 | 2014-11-25 | Seiko Epson Corporation | Ink set, ink-jet recording method, and recorded material |
| JP5224699B2 (ja) | 2007-03-01 | 2013-07-03 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、平版印刷版の製造方法、及び平版印刷版 |
| JP5238292B2 (ja) | 2007-03-23 | 2013-07-17 | 三菱製紙株式会社 | 水現像可能な感光性平版印刷版材料 |
| JP5243072B2 (ja) | 2007-03-30 | 2013-07-24 | 富士フイルム株式会社 | インク組成物、並びに、それを用いた画像記録方法及び画像記録物 |
| JP5306681B2 (ja) | 2007-03-30 | 2013-10-02 | 富士フイルム株式会社 | 重合性化合物、重合体、インク組成物、印刷物及びインクジェット記録方法 |
| EP2028241A1 (en) * | 2007-08-09 | 2009-02-25 | Seiko Epson Corporation | Photocurable ink composition, ink cartridge, inkjet recording method and recorded matter |
| JP4816976B2 (ja) * | 2007-08-09 | 2011-11-16 | セイコーエプソン株式会社 | 光硬化型インク組成物 |
| EP2033949B1 (en) * | 2007-09-04 | 2017-04-19 | Agfa Graphics N.V. | Radiation curable compositions for food applications |
| JP4766281B2 (ja) * | 2007-09-18 | 2011-09-07 | セイコーエプソン株式会社 | インクジェット記録用非水系インク組成物、インクジェット記録方法および記録物 |
| JP5227560B2 (ja) | 2007-09-28 | 2013-07-03 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、及び、成形印刷物の製造方法 |
| JP5265165B2 (ja) | 2007-09-28 | 2013-08-14 | 富士フイルム株式会社 | 塗布装置及びこれを用いるインクジェット記録装置 |
| JP4898618B2 (ja) | 2007-09-28 | 2012-03-21 | 富士フイルム株式会社 | インクジェット記録方法 |
| ATE507268T1 (de) * | 2007-10-24 | 2011-05-15 | Agfa Graphics Nv | Härtbare flüssigkeiten und tinten für spielzeuge und lebensmittelverpackungen |
| EP2065362A1 (en) * | 2007-11-29 | 2009-06-03 | Agfa Graphics N.V. | Preparation method of copolymerizable photoinitiators |
| JP5254632B2 (ja) | 2008-02-07 | 2013-08-07 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、及び、成形印刷物 |
| US20090214797A1 (en) | 2008-02-25 | 2009-08-27 | Fujifilm Corporation | Inkjet ink composition, and inkjet recording method and printed material employing same |
| JP2009269397A (ja) | 2008-02-29 | 2009-11-19 | Seiko Epson Corp | 不透明層の形成方法、記録方法、インクセット、インクカートリッジ、記録装置 |
| JP5583329B2 (ja) | 2008-03-11 | 2014-09-03 | 富士フイルム株式会社 | 顔料組成物、インク組成物、印刷物、インクジェット記録方法、及びポリアリルアミン誘導体 |
| JP4914862B2 (ja) | 2008-03-26 | 2012-04-11 | 富士フイルム株式会社 | インクジェット記録方法、及び、インクジェット記録装置 |
| JP5414367B2 (ja) | 2008-06-02 | 2014-02-12 | 富士フイルム株式会社 | 顔料分散物及びそれを用いたインク組成物 |
| JP5383133B2 (ja) | 2008-09-19 | 2014-01-08 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法及び印刷物成形体の製造方法 |
| JP2010077228A (ja) | 2008-09-25 | 2010-04-08 | Fujifilm Corp | インク組成物、インクジェット記録方法、及び、印刷物 |
| EP2199273B1 (en) | 2008-12-18 | 2018-02-21 | Agfa Nv | Polymerizable photoinitiators and radiation curable compositions |
| JP2010180330A (ja) | 2009-02-05 | 2010-08-19 | Fujifilm Corp | 非水系インク、インクセット、画像記録方法、画像記録装置、および記録物 |
| JP5350827B2 (ja) | 2009-02-09 | 2013-11-27 | 富士フイルム株式会社 | インク組成物、及び、インクジェット記録方法 |
| JP2010209183A (ja) | 2009-03-09 | 2010-09-24 | Fujifilm Corp | インク組成物及びインクジェット記録方法 |
| JP5349095B2 (ja) | 2009-03-17 | 2013-11-20 | 富士フイルム株式会社 | インク組成物、及び、インクジェット記録方法 |
| JP5349097B2 (ja) | 2009-03-19 | 2013-11-20 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、及び、成形印刷物の製造方法 |
| JP5383289B2 (ja) | 2009-03-31 | 2014-01-08 | 富士フイルム株式会社 | インク組成物、インクジェット用であるインク組成物、インクジェット記録方法、およびインクジェット法による印刷物 |
| JP5572026B2 (ja) | 2009-09-18 | 2014-08-13 | 富士フイルム株式会社 | インク組成物、及び、インクジェット記録方法 |
| JP5530141B2 (ja) | 2009-09-29 | 2014-06-25 | 富士フイルム株式会社 | インク組成物及びインクジェット記録方法 |
| JP2011152747A (ja) * | 2010-01-28 | 2011-08-11 | Seiko Epson Corp | 水性インク組成物、およびインクジェット記録方法ならびに記録物 |
| JP5692490B2 (ja) * | 2010-01-28 | 2015-04-01 | セイコーエプソン株式会社 | 水性インク組成物、およびインクジェット記録方法ならびに記録物 |
| TWI516473B (zh) * | 2010-03-05 | 2016-01-11 | 國立大學法人名古屋大學 | α－醯氧基羰基化合物之製法及新穎α－醯氧基羰基化合物 |
| WO2011122473A1 (ja) | 2010-03-29 | 2011-10-06 | 三菱製紙株式会社 | 感光性組成物及び感光性平版印刷版材料 |
| JP5554114B2 (ja) | 2010-03-29 | 2014-07-23 | 富士フイルム株式会社 | 活性放射線硬化型インクジェット用インク組成物、印刷物、印刷物の製造方法、印刷物成形体、及び印刷物成形体の製造方法 |
| US8573765B2 (en) | 2010-03-31 | 2013-11-05 | Fujifilm Corporation | Active radiation curable ink composition, ink composition for inkjet recording, printed matter, and method of producing molded article of printed matter |
| WO2011139933A2 (en) * | 2010-05-03 | 2011-11-10 | Dentsply International Inc. | Low stress flowable dental composition |
| CN102336081A (zh) | 2010-05-19 | 2012-02-01 | 富士胶片株式会社 | 印刷方法、套印物的制作方法、层压加工方法、发光二极管固化性涂布组合物及墨液组合物 |
| JP5606817B2 (ja) | 2010-07-27 | 2014-10-15 | 富士フイルム株式会社 | 活性放射線硬化型インクジェット用インク組成物、印刷物、印刷物成形体、及び印刷物の製造方法 |
| EP2423277A3 (en) | 2010-08-27 | 2012-05-09 | Fujifilm Corporation | Ink composition for inkjet recording, inkjet recording method and inkjet printed article |
| EP3124557B1 (en) | 2011-02-28 | 2018-08-22 | Fujifilm Corporation | Ink composition and image forming method |
| JP2012201874A (ja) | 2011-03-28 | 2012-10-22 | Fujifilm Corp | インク組成物、及び画像形成方法 |
| JP5300904B2 (ja) | 2011-03-31 | 2013-09-25 | 富士フイルム株式会社 | インク組成物及び画像形成方法 |
| JP5764416B2 (ja) | 2011-07-08 | 2015-08-19 | 富士フイルム株式会社 | インク組成物及び画像形成方法 |
| CN103842449B (zh) | 2011-09-29 | 2015-12-23 | 富士胶片株式会社 | 喷墨油墨组合物及喷墨记录方法 |
| WO2013089204A1 (ja) | 2011-12-15 | 2013-06-20 | 旭硝子株式会社 | 撥液性化合物、撥液性重合体、硬化性組成物、塗布用組成物、ならびに硬化膜を有する物品、親液性領域と撥液性領域とのパターンを有する物品およびその製造方法 |
| EP2604663B1 (en) | 2011-12-16 | 2017-08-09 | Agfa Graphics N.V. | Curable liquids and inkjet inks for food packaging applications |
| JP5770765B2 (ja) | 2012-03-09 | 2015-08-26 | 富士フイルム株式会社 | 放射線硬化型インクジェットインクセット及びインクジェット記録方法 |
| EP2644664B1 (en) | 2012-03-29 | 2015-07-29 | Fujifilm Corporation | Actinic radiation-curing type ink composition, inkjet recording method, decorative sheet, decorative sheet molded product, process for producing in-mold molded article, and in-mold molded article |
| JP5606567B2 (ja) | 2012-04-19 | 2014-10-15 | 富士フイルム株式会社 | 活性光線硬化型インク組成物、インクジェット記録方法、加飾シート、加飾シート成形物、インモールド成形品の製造方法及びインモールド成形品 |
| CN104603168B (zh) | 2012-09-14 | 2016-07-06 | 富士胶片株式会社 | 固化性组合物及图像形成方法 |
| CN104684634B (zh) | 2012-09-28 | 2017-04-26 | 富士胶片株式会社 | 高分子功能性膜及其制造方法 |
| SG11201502454PA (en) | 2012-09-28 | 2015-06-29 | Fujifilm Corp | Functional polymer membrane, and method of producing same |
| JP6126498B2 (ja) | 2013-02-15 | 2017-05-10 | 富士フイルム株式会社 | 高分子機能性膜及びその製造方法 |
| WO2014136697A1 (ja) | 2013-03-07 | 2014-09-12 | 富士フイルム株式会社 | 高分子機能性膜、その製造方法、高分子機能性膜を具備したイオン交換膜およびプロトン伝導膜、およびイオン交換装置 |
| JP5980702B2 (ja) | 2013-03-07 | 2016-08-31 | 富士フイルム株式会社 | インクジェットインク組成物、インクジェット記録方法、及び、成型印刷物の製造方法 |
| JP6004971B2 (ja) | 2013-03-12 | 2016-10-12 | 富士フイルム株式会社 | 加飾シート成形物又はインモールド成形品製造用インクジェットインク組成物、加飾シート成形物又はインモールド成形品製造用インクジェット記録方法、加飾シート成形物又はインモールド成形品製造用インクセット、加飾シート成形物又はインモールド成形品製造用加飾シート、加飾シート成形物、及び、インモールド成形品の製造方法 |
| JP5939644B2 (ja) | 2013-08-30 | 2016-06-22 | 富士フイルム株式会社 | 画像形成方法、インモールド成型品の製造方法、及び、インクセット |
| AT514594B1 (de) | 2013-09-06 | 2015-02-15 | Durst Phototech Digital Tech | Photoinitiator |
| JP6066960B2 (ja) | 2014-05-30 | 2017-01-25 | 富士フイルム株式会社 | 成形加工用活性光線硬化型インク組成物、インクセット、インクジェット記録方法、成形加工用加飾シート、加飾シート成形物及びインモールド成形品の製造方法 |
| CN105152898B (zh) * | 2015-06-23 | 2017-04-26 | 杭华油墨股份有限公司 | 苯基丁酮衍生物与其作为光引发剂的应用 |
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Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2443414C2 (de) * | 1974-09-11 | 1983-05-19 | Beiersdorf Ag, 2000 Hamburg | Verfahren zur Herstellung von selbstklebend ausgerüsteten Produkten |
| US4469774A (en) * | 1983-03-28 | 1984-09-04 | E. I. Du Pont De Nemours And Company | Positive-working photosensitive benzoin esters |
| JPS6150939A (ja) * | 1984-08-17 | 1986-03-13 | Mitsui Toatsu Chem Inc | アクリロイロキシプロピオフエノン誘導体及びその用途 |
-
1985
- 1985-09-28 DE DE19853534645 patent/DE3534645A1/de not_active Withdrawn
-
1986
- 1986-09-09 AU AU62470/86A patent/AU595830B2/en not_active Ceased
- 1986-09-10 CS CS866523A patent/CS257798B2/cs unknown
- 1986-09-13 DE DE8686112676T patent/DE3682858D1/de not_active Expired - Lifetime
- 1986-09-13 AT AT86112676T patent/ATE70258T1/de not_active IP Right Cessation
- 1986-09-13 EP EP86112676A patent/EP0217205B1/de not_active Expired - Lifetime
- 1986-09-25 ES ES8602162A patent/ES2004660A6/es not_active Expired
- 1986-09-26 FI FI863894A patent/FI89162C/sv not_active IP Right Cessation
- 1986-09-26 AR AR86305384A patent/AR241265A1/es active
- 1986-09-26 DK DK461886A patent/DK172255B1/da not_active IP Right Cessation
- 1986-09-26 JP JP61226362A patent/JP2514804B2/ja not_active Expired - Fee Related
- 1986-09-26 ZA ZA867370A patent/ZA867370B/xx unknown
- 1986-09-26 DD DD86294723A patent/DD258614A5/de not_active IP Right Cessation
- 1986-09-26 BR BR8604672A patent/BR8604672A/pt active Search and Examination
- 1986-09-26 HU HU864118A patent/HU201510B/hu not_active IP Right Cessation
- 1986-09-26 PL PL1986261574A patent/PL149572B2/pl unknown
- 1986-09-26 CA CA000519146A patent/CA1275109A/en not_active Expired - Lifetime
- 1986-09-29 US US06/912,473 patent/US4922004A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK461886D0 (da) | 1986-09-26 |
| FI863894A0 (fi) | 1986-09-26 |
| EP0217205A3 (en) | 1988-09-21 |
| ATE70258T1 (de) | 1991-12-15 |
| CA1275109A (en) | 1990-10-09 |
| PL261574A2 (en) | 1987-10-19 |
| DK172255B1 (da) | 1998-02-09 |
| US4922004A (en) | 1990-05-01 |
| AU595830B2 (en) | 1990-04-12 |
| JP2514804B2 (ja) | 1996-07-10 |
| HU201510B (en) | 1990-11-28 |
| FI89162C (sv) | 1993-08-25 |
| DK461886A (da) | 1987-03-29 |
| JPS6281345A (ja) | 1987-04-14 |
| AU6247086A (en) | 1987-04-02 |
| FI863894A (fi) | 1987-03-29 |
| EP0217205B1 (de) | 1991-12-11 |
| BR8604672A (pt) | 1987-06-16 |
| DD258614A5 (de) | 1988-07-27 |
| HUT43027A (en) | 1987-09-28 |
| AR241265A1 (es) | 1992-04-30 |
| PL149572B2 (en) | 1990-02-28 |
| CS257798B2 (en) | 1988-06-15 |
| DE3682858D1 (de) | 1992-01-23 |
| DE3534645A1 (de) | 1987-04-02 |
| ES2004660A6 (es) | 1989-02-01 |
| ZA867370B (en) | 1987-05-27 |
| EP0217205A2 (de) | 1987-04-08 |
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Owner name: CIBA-GEIGY AG |