JP6745630B2 - (メタ)アクリレート樹脂及び印刷インキ - Google Patents
(メタ)アクリレート樹脂及び印刷インキ Download PDFInfo
- Publication number
- JP6745630B2 JP6745630B2 JP2016075158A JP2016075158A JP6745630B2 JP 6745630 B2 JP6745630 B2 JP 6745630B2 JP 2016075158 A JP2016075158 A JP 2016075158A JP 2016075158 A JP2016075158 A JP 2016075158A JP 6745630 B2 JP6745630 B2 JP 6745630B2
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- JP
- Japan
- Prior art keywords
- meth
- acrylate
- compound
- compounds
- printing ink
- 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.)
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- 238000007639 printing Methods 0.000 title claims description 55
- 239000004925 Acrylic resin Substances 0.000 title claims description 44
- -1 acrylate compound Chemical class 0.000 claims description 114
- 150000001875 compounds Chemical class 0.000 claims description 71
- 125000001931 aliphatic group Chemical group 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 229920005862 polyol Polymers 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- 239000002994 raw material Substances 0.000 claims description 20
- 239000005056 polyisocyanate Substances 0.000 claims description 19
- 229920001228 polyisocyanate Polymers 0.000 claims description 19
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 57
- 239000000976 ink Substances 0.000 description 40
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 31
- 239000000049 pigment Substances 0.000 description 30
- 239000000047 product Substances 0.000 description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- 239000011347 resin Substances 0.000 description 15
- 229920005989 resin Polymers 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 150000002430 hydrocarbons Chemical group 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 229920000193 polymethacrylate Polymers 0.000 description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 10
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000003505 polymerization initiator Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 5
- 239000004606 Fillers/Extenders Substances 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 150000002596 lactones Chemical class 0.000 description 5
- 238000007645 offset printing Methods 0.000 description 5
- 229920006389 polyphenyl polymer Polymers 0.000 description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 4
- 239000004641 Diallyl-phthalate Substances 0.000 description 4
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 4
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 3
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 239000003504 photosensitizing agent Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 3
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- QOFLTGDAZLWRMJ-UHFFFAOYSA-N 2-methylpropane-1,1-diol Chemical compound CC(C)C(O)O QOFLTGDAZLWRMJ-UHFFFAOYSA-N 0.000 description 2
- YHFGMFYKZBWPRW-UHFFFAOYSA-N 3-methylpentane-1,1-diol Chemical compound CCC(C)CC(O)O YHFGMFYKZBWPRW-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
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-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
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- BKNMHPNFWBRRFC-UHFFFAOYSA-N (2-hydroxy-1-phenylethyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)C1=CC=CC=C1 BKNMHPNFWBRRFC-UHFFFAOYSA-N 0.000 description 1
- NSIHCJDYMGWYKW-UHFFFAOYSA-N (2-hydroxy-2-phenylethyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)C1=CC=CC=C1 NSIHCJDYMGWYKW-UHFFFAOYSA-N 0.000 description 1
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- NIUHGYUFFPSEOW-UHFFFAOYSA-N (4-hydroxyphenyl) prop-2-enoate Chemical compound OC1=CC=C(OC(=O)C=C)C=C1 NIUHGYUFFPSEOW-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- GWSURTDMLUFMJH-FOCLMDBBSA-N (e)-hexadec-1-en-1-ol Chemical compound CCCCCCCCCCCCCC\C=C\O GWSURTDMLUFMJH-FOCLMDBBSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- VYMSWGOFSKMMCE-UHFFFAOYSA-N 10-butyl-2-chloroacridin-9-one Chemical compound ClC1=CC=C2N(CCCC)C3=CC=CC=C3C(=O)C2=C1 VYMSWGOFSKMMCE-UHFFFAOYSA-N 0.000 description 1
- GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- YBVRFTBNIZWMSK-UHFFFAOYSA-N 2,2-dimethyl-1-phenylpropan-1-ol Chemical compound CC(C)(C)C(O)C1=CC=CC=C1 YBVRFTBNIZWMSK-UHFFFAOYSA-N 0.000 description 1
- UXCIJKOCUAQMKD-UHFFFAOYSA-N 2,4-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3SC2=C1 UXCIJKOCUAQMKD-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- LZHUBCULTHIFNO-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(OCCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCO)C=C1 LZHUBCULTHIFNO-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- YSUGIEHWIVGUDE-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethyl prop-2-enoate Chemical compound OC1=CC=C(CCOC(=O)C=C)C=C1 YSUGIEHWIVGUDE-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- CWNOEVURTVLUNV-UHFFFAOYSA-N 2-(propoxymethyl)oxirane Chemical compound CCCOCC1CO1 CWNOEVURTVLUNV-UHFFFAOYSA-N 0.000 description 1
- AJOPUMVHMNKYCQ-UHFFFAOYSA-N 2-benzoylbenzoic acid;(2-methyl-4-phenylphenyl)-phenylmethanone Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1.CC1=CC(C=2C=CC=CC=2)=CC=C1C(=O)C1=CC=CC=C1 AJOPUMVHMNKYCQ-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-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
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- Inks, Pencil-Leads, Or Crayons (AREA)
- Macromonomer-Based Addition Polymer (AREA)
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- Polyurethanes Or Polyureas (AREA)
Description
の何れかで表される分子構造を有するモノヒドロキシ化合物(A1)や、下記構造式(4)〜(6)
の何れかで表されるカルボキシ化合物と、ポリオール化合物とのエステル化物であって、分子構造中に一つ乃至複数の不飽和結合を有するモノヒドロキシ化合物(A2)、下記構造式(7)〜(9)
の何れかで表されるモノヒドロキシ化合物と、モノヒドロキシカルボン酸化合物とのエステル化物であって、分子構造中に一つ乃至複数の不飽和結合を有するモノヒドロキシ化合物(A3)等が挙げられる。
で表される繰り返し構造を有するポリメチレンポリフェニルポリイソシアネート;これらのイソシアヌレート変性体、アダクト変性体、ビウレット変性体、アロファネート変性体等が挙げられる。これらはそれぞれ単独で使用しても良いし、2種類以上を併用しても良い。
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
[機種] 日本分光株式会社製 FT/IR−4100
[測定条件]イソシアネート基を示す2250cm-1の赤外吸収スペクトルを確認することで反応完結を確認した。
重量平均分子量(Mw)は、下記条件のゲルパーミアーションクロマトグラフィー(GPC)により測定した。
測定装置 ;東ソー株式会社製 HLC−8220GPC
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
撹拌機、ガス導入管、コンデンサー、及び温度計を備えた四つ口フラスコに、下記構造式(4−1)で表される繰り返し構造を有するポリメチレンポリフェニルポリイソシアネート(BASF INOAC ポリウレタン株式会社製「ルプラネートM20S」:イソシアネート基含有量31質量%)58.9質量部、ターシャリブチルヒドロキシトルエン0.5質量部、メトキシハイドロキノン0.05質量部、オクチル酸亜鉛0.02質量部を加え、50℃に昇温した。反応系中を撹拌しながら、2−ヒドロキシエチルアクリレート35.2質量部及びオレイルアルコール〔(9Z)−9−オクタデセン−1−オール〕2質量部を1時間かけて滴下した。90℃で3時間反応させた後、グリセリン4質量部を添加した。90℃で反応を続け、イソシアネート基を示す2250cm−1の赤外吸収スペクトルが消失したことを確認し、(メタ)アクリレート樹脂(1)を得た。(メタ)アクリレート樹脂(1)の重量平均分子量(Mw)は5,492、反応原料から算出される(メタ)アクリロイル基含有量の理論値は3.03mmol/gであった。
各原料成分の種類及び使用量を下記表1に示す通りに変更した以外は実施例1と同様にして(メタ)アクリレート樹脂(2)〜(9)を得た。
撹拌機、ガス導入管、コンデンサー、及び温度計を備えた四つ口フラスコに、トリレンジイソシアネート16.3質量部、ターシャリブチルヒドロキシトルエン0.1質量部、メトキシハイドロキノン0.02質量部、オクチル酸亜鉛0.02質量部を加え、75℃に昇温し、2−ヒドロキシエチルアクリレート3.7質量部を1時間にわたって攪拌下で滴下した。滴下後、75℃で3時間反応させた後、第二工程として、ポリプロピレングリコール(三井化学製「アクトコールD−3000」数平均分子量3000)80.0質量部を添加し、さらに75℃で反応させ、イソシアネート基を示す2250cm−1の赤外吸収スペクトルが消失するまで反応を行い、(メタ)アクリレート樹脂(1’)を得た。(メタ)アクリレート樹脂(1’)の重量平均分子量(Mw)は5,680、反応原料から算出される(メタ)アクリロイル基含有量の理論値は0.32mmol/gであった。
下記表2、3に示す割合で各成分を配合し、ミキサー(単軸ディゾルバー)を用いて撹拌した後、配合物を3本ロールミルを用いて練肉し、印刷インキを調製した。得られた印刷インキについて、下記条件で種々の評価を行った。結果を表2、3に示す。
その他の(メタ)アクリレート化合物(X−1):エチレンオキサイド変性トリメチロールプロパントリアクリレート(MIWON社製「MIRAMER M3130」粘度:50−70mPa・s(25℃)、1分子あたりのエチレンオキサイド平均付加数:3)
顔料:DIC株式会社製「SYMULER FAST YELLOW 4342」
体質顔料:含水ケイ酸マグネシウム(松村産業社製体質顔料「ハイフィラー#5000PJ」)
ワックス:ポリオレフィンワックス(シャムロック社製ワックス「S−381−N1」)
重合禁止剤:N−ニトロソフェニルヒドロキシルアミシアルミニウム塩(和光純薬工業(株)製「Q−1301」)
重合開始剤(Y−1):α-アミノアルキルフェノン(BASF社製「Irgacure907」)
重合開始剤(Y−2):4,4’−ビスジメチルアミノベンゾフェノン(大同化成社製「EAB−SS」)
スプレッドメーター法(平行板粘度計)によりJIS K5101,5701に則った方法で測定を実施した。水平に置いた2枚の平行板の間に挟まれた印刷インキが、荷重板の自重(115グラム)によって、同心円状に広がる特性を経時的に観察し、60秒後のインキの広がり直径(mm)をダイアメーター値として評価とした。評価基準は以下の通り。
A:ダイアメーター値が37mm以上
B:ダイアメーター値が34mm以上 37mm未満
C:ダイアメーター値が34mm未満
25℃に空調した室内において、地平面と70゜の角度をなすガラス板の上端に印刷インキ1.0mlを置き、1日後に流動した距離を測定した。数値が大きいほど流動性が良好であることを示す。
インコメーター式ミスチング試験機に印刷インキ1.31ml載せて、機械温度32℃、1200rpmで三分間回転させた。回転に伴い印刷インキが飛び回転体に沿って並べた紙の質量増加変化でミスチングの優劣を比較した。耐ミスチング性が悪い場合は印刷インキの飛ぶ量が増加し紙の質量が増える。
(評価基準)
A:0.050g未満
B:0.050g以上 0.075g未満
C:0.075g以上
簡易展色機(RIテスター、豊栄精工社製)を用い、前記印刷インキ0.10mlを使用して、RIテスターのゴムロール及び金属ロール上に均一に引き伸ばし、透明PETタック紙(DIC製「ダイタック UVPET透明25EMH−S」)の表面に約220cm2の面積範囲に均一に塗布されるように展色し、展色物を作製した。
印刷インキ塗布後の展色物に紫外線(UV)照射を行い、印刷インキを硬化させて、印刷物を得た。具体的には、水冷メタルハライドランプ(出力100W/cm 1灯)およびベルトコンベアを搭載したUV照射装置(アイグラフィックス社製、コールドミラー付属)を使用し、展色物をコンベア上に載せ、ランプ直下(照射距離11cm)を以下に述べる所定条件で通過させた。各条件における紫外線照射量は紫外線積算光量系(ウシオ電機社製UNIMETER UIT−150−A/受光機UVD−C365)を用いて測定した。
硬化性は、照射直後に爪スクラッチ法にて印刷物表面の傷付きの有無を確認した。前記UV照射装置のコンベア速度(m/分)を変化させながら展色物に紫外線を照射し、硬化後に爪で強く擦っても傷付きが無い最速のコンベア速度(m/分)を記載した。コンベア速度の数値が大きいほど印刷インキの硬化性が良好であることを示す。
簡易展色機(RIテスター、豊栄精工社製)を用い、硬化性評価で用いた展色物上にwet‐onでUV硬化型オーバープリントニス(DIC製「UVカルトン ACT OPニス」)0.15mlを重ね刷りした。硬化性評価と同条件のUV照射装置で、コンベア速度を30m/分に設定し、印刷インキ及びオーバープリントニスを硬化させた。得られた印刷物について、印刷表面の光沢を測定し、評価した。光沢の数値が高いほどインキのオーバープリントニス受理性が良好であることを示す。
(評価基準)
A:光沢55以上
B:光沢45以上 55未満
C:光沢45未満
Claims (6)
- 炭素原子数4〜50の脂肪族不飽和炭化水素基を有するモノヒドロキシ化合物(A)、モノヒドロキシ(メタ)アクリレート化合物(B)、ポリイソシアネート化合物(C)及び脂肪族ポリオール化合物を必須の反応原料とする(メタ)アクリレート樹脂と、
その他の(メタ)アクリレート化合物(X)とを含有する硬化性組成物であって、
前記(メタ)アクリレート化合物(X)が、
ポリオキシアルキレン変性トリ(メタ)アクリレート化合物を含むものであることを特徴とする硬化性組成物。 - 反応原料の合計100質量部中、0.1〜30質量部が前記炭素原子数4〜50の脂肪族不飽和炭化水素基を有するモノヒドロキシ化合物(A)である請求項1記載の硬化性組成物。
- 前記ポリイソシアネート化合物(C)が、分子構造中に芳香環を有するポリイソシアネート化合物である請求項1記載の硬化性組成物。
- 重量平均分子量(Mw)が1,000〜30,000の範囲である請求項1記載の硬化性組成物。
- 請求項1〜4のいずれか1項記載の硬化性組成物を用いてなる印刷インキ。
- 請求項5記載の印刷インキを印刷してなる印刷物。
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