JPH04202425A - Actinc radiation-curable resin composition and printing ink composition - Google Patents
Actinc radiation-curable resin composition and printing ink compositionInfo
- Publication number
- JPH04202425A JPH04202425A JP2335563A JP33556390A JPH04202425A JP H04202425 A JPH04202425 A JP H04202425A JP 2335563 A JP2335563 A JP 2335563A JP 33556390 A JP33556390 A JP 33556390A JP H04202425 A JPH04202425 A JP H04202425A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acid
- acrylate
- resin composition
- 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.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 12
- 239000000203 mixture Substances 0.000 title claims abstract description 10
- YWGAKIGNXGAAQR-DLPAQYCSSA-N C1([C@H]2CC(=O)N[C@@H](CC)C(=O)N3C[C@@H](Cl)[C@@H](Cl)[C@H]3C(=O)N[C@H](C(N[C@@H](CO)C(=O)N2)=O)CC)=CC=CC=C1 Chemical compound C1([C@H]2CC(=O)N[C@@H](CC)C(=O)N3C[C@@H](Cl)[C@@H](Cl)[C@H]3C(=O)N[C@H](C(N[C@@H](CO)C(=O)N2)=O)CC)=CC=CC=C1 YWGAKIGNXGAAQR-DLPAQYCSSA-N 0.000 title 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 229920000180 alkyd Polymers 0.000 claims abstract description 6
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims description 9
- 239000000049 pigment Substances 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 5
- 239000007870 radical polymerization initiator Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 229920005989 resin Polymers 0.000 abstract description 6
- 239000011347 resin Substances 0.000 abstract description 6
- 238000010186 staining Methods 0.000 abstract description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 71
- 239000002253 acid Substances 0.000 description 30
- -1 pentyl glycol Chemical compound 0.000 description 12
- 239000000976 ink Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000008199 coating composition Substances 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 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 3
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 3
- 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 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940105990 diglycerin Drugs 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- ZHQLTKAVLJKSKR-UHFFFAOYSA-N homophthalic acid Chemical compound OC(=O)CC1=CC=CC=C1C(O)=O ZHQLTKAVLJKSKR-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
- IQVLXQGNLCPZCL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate Chemical compound CC(C)(C)OC(=O)NCCCCC(NC(=O)OC(C)(C)C)C(=O)ON1C(=O)CCC1=O IQVLXQGNLCPZCL-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 description 1
- QDCPNGVVOWVKJG-VAWYXSNFSA-N 2-[(e)-dodec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-VAWYXSNFSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OJVQNVMHJWSOSY-UHFFFAOYSA-N 3-methylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(O)=O)(C)C2C(O)=O OJVQNVMHJWSOSY-UHFFFAOYSA-N 0.000 description 1
- BNDWRWFZSMPKQP-UHFFFAOYSA-N 3-pentadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCC=CC1CC(=O)OC1=O BNDWRWFZSMPKQP-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
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- 235000021314 Palmitic acid Nutrition 0.000 description 1
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- 235000021355 Stearic acid Nutrition 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
- QNSOHXTZPUMONC-UHFFFAOYSA-N benzene pentacarboxylic acid Natural products OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O QNSOHXTZPUMONC-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- 238000007664 blowing Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
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- 229920001577 copolymer Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
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- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 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 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid 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
- 239000000021 stimulant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N trihydroxybenzene Natural products OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
【発明の詳細な説明】
［発明の目的］
（産業上の利用分野）
本発明は活性エネルギー線硬化性樹脂組成物に関し、特
に紫外線もしくは電子線などの照射による硬化する被覆
組成物および印刷インキ組成物に有用な樹脂組成物に関
する。Detailed Description of the Invention [Object of the Invention] (Industrial Application Field) The present invention relates to active energy ray-curable resin compositions, and particularly coating compositions and printing ink compositions that are cured by irradiation with ultraviolet rays or electron beams. The present invention relates to a resin composition useful for products.
（従来の技術）
近年、活性エネルギー線による硬化性被覆組成物の研究
は盛んに行なわれており、その中でも印刷インキ、クリ
ヤーワニス、塗料、接着剤、フォトレジスト等の分野で
実用化が進められている。(Prior art) In recent years, research has been actively conducted on coating compositions that can be cured by active energy rays, and practical applications are progressing in the fields of printing inks, clear varnishes, paints, adhesives, photoresists, etc. ing.
これらはラジカル重合性を有する樹脂およびモノマーと
、必要に応じてラジカル重合開始剤、顔料からなってお
り、ラジカル重合性を有する樹脂としてはアルキッド（
メタ）アクリレート、ポリエステル（メタ）アクリレー
ト、エポキシ（メタ）アクリレート、ウレタン変性（メ
タ）アクリレート等が、ま１こ七ツマ−としては、ビス
フェノールＡアルキレンオキサイド付加体ジ（メタ）ア
クリレート、ネオペンチルグリコールジ（メタ）アクリ
レート、トリメチロールプロパントリ （メタ）アクリ
レート、テトラメチロールメタンテトラ（メタ）アクリ
レート、ジペンタエリスリトールヘキサ（メタ）アクリ
レート、アルキルフェノールアルキレンオキサイド付加
体モノ （メタ）アクリレート等が用いられていた。な
お、本明細書において（メタ）アクリレートとは、アク
リレートおよびもしくはメタクリレートを、また（メタ
）アクリル酸とはアクリル酸およびもしくはメタクリル
酸を示す。These are composed of radically polymerizable resins and monomers, as well as radical polymerization initiators and pigments as necessary.As radically polymerizable resins, alkyds (
Meth)acrylate, polyester (meth)acrylate, epoxy (meth)acrylate, urethane-modified (meth)acrylate, etc., as well as bisphenol A alkylene oxide adduct di(meth)acrylate, neopentyl glycol di (meth)acrylate, trimethylolpropane tri(meth)acrylate, tetramethylolmethanetetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, alkylphenol alkylene oxide adduct mono(meth)acrylate, etc. were used. In this specification, (meth)acrylate refers to acrylate and/or methacrylate, and (meth)acrylic acid refers to acrylic acid and/or methacrylic acid.
しかし、これらの化合物を用いた硬化性被覆組成物は例
えば、印刷インキに用いた場合、印刷時の汚れ、インキ
の乳化により転移不良が生しることが多い。したがって
、これらの硬化性被覆剤の適用範囲を狭めているのが実
状であった。However, when a curable coating composition using these compounds is used, for example, in a printing ink, poor transfer often occurs due to staining during printing and emulsification of the ink. Therefore, the actual situation is that the scope of application of these curable coating materials has been narrowed.
この問題を解決するため、エポンエステルあるいは常温
固体のジアリルフタレートポリマーをラジカルニ重結合
を有するモノマーもしくはプレポリマーに？容解したビ
ヒクルを用いることにより、印刷適性を改良しようとす
る試みもあるか、印刷時の汚れにおいて未だ解決すべき
問題点がある。In order to solve this problem, we changed Epon ester or diallyl phthalate polymer, which is solid at room temperature, to a monomer or prepolymer with radical double bonds. There have been attempts to improve the printability by using a soluble vehicle, but there are still problems to be solved in printing smudges.
（発明が解決しようとする課題）
本発明は、特に上記のような印刷時の汚れ、転移不良を
解決した活性エネルギー線硬化性樹脂組成物およびそれ
を用いた印刷インキ組成物を提供するものである。(Problems to be Solved by the Invention) The present invention provides an active energy ray-curable resin composition and a printing ink composition using the same, which particularly solves the problems of staining and poor transfer during printing as described above. be.
［発明の構成］
（課題を解決するための手段）
１、多価アルコール成分として下記化合物（Ａ） 、
（Ｂ）および（Ｃ）から選ばれる少くなくとも１種を用
いてなる水酸基過剰のアルキッド樹脂に（メタ）アクリ
ル酸と反応せしめてなることを特徴とする活性エネルギ
ー線硬化性樹脂組成物。[Structure of the invention] (Means for solving the problem) 1. The following compound (A) as a polyhydric alcohol component,
An active energy ray-curable resin composition, characterized in that it is made by reacting an alkyd resin with an excess of hydroxyl groups using at least one selected from (B) and (C) with (meth)acrylic acid.
ＣＨｚＯＨＣＨｚＯ）Ｉ
（Ａ） ’ （Ｂ）
ＣＨｌｌ−Ｃ）＋２−Ｃ）＋２−ＣＨ−ＣＨ−ＣＨ２−
ＯＨ□
ＣＨｚ−ＣＨ３
（Ｃ）
２、請求項１の樹脂組成物、活性工翠ルギー線硬化性モ
ノマー、顔料及び必要に応してラジカル重合開始剤を含
むことを特徴とする活性工ぶルギー線硬化性印刷インキ
組成物。CHzOHCHzO)I (A) ' (B) CHll-C)+2-C)+2-CH-CH-CH2-
OH□ CHz-CH3 (C) 2. An activated activated energy beam characterized by containing the resin composition of claim 1, an activated activated energy radiation curable monomer, a pigment, and, if necessary, a radical polymerization initiator. Curable printing ink composition.
ここでアルキッド樹脂とは、多価アルコール、多価カル
ホン酸、１価カルボン酸をエステル化反応して得られる
樹脂である。Here, the alkyd resin is a resin obtained by esterifying polyhydric alcohol, polycarboxylic acid, and monohydric carboxylic acid.
本発明は多価アルコール成分として化合物（Ａ）１（Ｂ
）又は（Ｃ）を使用する。さらに他の多価アルコール例
えば、エチレングリコール、ジエチレングリコール、ト
リエチレングリコール、ポリエチレングリコール、プロ
ピレングリコール、ジプロピレングリコール、トリプロ
ピレングリコール、ポリプロピレングリコール、ブチレ
ングリコール、ペンチルグリコール、ネオペンチルグリ
コール、ヘキサンジオール、グリセリン、ジグリセリン
、トリメチロールプロパン、ジトリメチロールプロパン
、トリメチコールエタン、シト・リメチロールエタン、
テトラメチロールメタン、ジペンタエリスリトール、ポ
リシクコペンタジエンジアリルアルコールコボリマー、
スピログリコールを併用して使用してもよい。The present invention uses compound (A) 1(B) as a polyhydric alcohol component.
) or (C). Furthermore, other polyhydric alcohols such as ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, butylene glycol, pentyl glycol, neopentyl glycol, hexanediol, glycerin, Glycerin, trimethylolpropane, ditrimethylolpropane, trimethylolethane, cytotrimethylolethane,
Tetramethylolmethane, dipentaerythritol, polycyclopentadiene diallyl alcohol copolymer,
Spiroglycol may also be used in combination.
又多価カルボン酸としては、例えば、シュウ酸、マロン
酸、コハク酸、ドデセニルコハク酸、ペンタデセニル無
水コハク酸、グリタル酸、マレインＭまたはそれらの酸
無水物、フマル酸、アジピン酸、ピメリン酸、スヘリン
酸、アゼライン酸、セバシン酸、０３Ｋ−ＤＡＳＬ−１
２，０３Ｋ−ＤＡＳＬ−２０，０３Ｋ−ＤＡＳＢ−１２
，０３Ｋ−ＤＡＳＢ−２０、○５Ｋ−ＤＡＬｉＬ−２０
．０３Ｋ−ＤＡＵＢ−２０（Ｏ３Ｋシリーズは間材製油
社製の長鎖二塩基酸）、アマニ油脂肪酸や桐油脂肪酸等
のダイマー酸などの脂肪族ジカルボン酸、０−フタル酸
、水添加Ｏ−フタル酸、メチル化水添ハイミック酸、メ
チルハイミック酸、ジフェン酸、トリメリット酸、ピロ
メリント酸、ナフタリン酸、ヘンヅフエノンテトラカル
ボン酸およびそれらの酸無水物、インフタル酸、テレフ
タル酸、ヘミメリト酸、トリメシン酸、ブレニド酸、メ
ロファン酸、ベンゼンペンタカルボン酸、ベンゼンヘキ
サカルボン酸、ホモフタル酸、０、ｍ、ｐ−フェニレン
酢酸、０−フェニレン酢酸−β−プロピオン酸等の芳香
族多価カルボン酸、ロジンのダイマー酸等が挙げられる
。Examples of polyvalent carboxylic acids include oxalic acid, malonic acid, succinic acid, dodecenyl succinic acid, pentadecenyl succinic anhydride, glitaric acid, maleic M or their acid anhydrides, fumaric acid, adipic acid, pimelic acid, and schelic acid. , azelaic acid, sebacic acid, 03K-DASL-1
2,03K-DASL-20,03K-DASB-12
, 03K-DASB-20, ○5K-DALiL-20
．． 03K-DAUB-20 (O3K series is a long-chain dibasic acid made by Kenzai Oil Co., Ltd.), aliphatic dicarboxylic acids such as dimer acids such as linseed oil fatty acids and tung oil fatty acids, O-phthalic acid, and water-added O-phthalic acids. , methylated hydrogenated hymic acid, methylhimic acid, diphenic acid, trimellitic acid, pyromellitic acid, naphthalic acid, henzphenonetetracarboxylic acid and their acid anhydrides, inphthalic acid, terephthalic acid, hemimellic acid, trimesine acids, aromatic polycarboxylic acids such as brenidic acid, merophanic acid, benzenepentacarboxylic acid, benzenehexacarboxylic acid, homophthalic acid, 0, m, p-phenyleneacetic acid, 0-phenyleneacetic acid-β-propionic acid, rosin. Examples include dimer acid.
一価カルボン酸としては、キ酸、酢酸、プロピオン酸、
酪酸、バレリアン酸、トリメチル酢酸、カブコン酸、ｎ
−へブタン酸、カプリル酸、ペラルゴン酸、メトキシ酢
酸、ヤシ油脂肪酸、パルミチン酸、ステアリン酸、オレ
イン酸、リノール酸、リルン酸等の脂肪族カルボン酸、
安息香酸、アルキル安息香酸、アルキルアミノ安息香酸
、フェニル酢酸、ハロゲン化安息香酸、アニス酸、ヘン
ジイル安息香酸、ナトフエ酸等の芳香族カルボン酸、ロ
ジン、水添加ロジン等がある。Monovalent carboxylic acids include chloric acid, acetic acid, propionic acid,
butyric acid, valeric acid, trimethylacetic acid, cabconic acid, n
- aliphatic carboxylic acids such as hebutanoic acid, caprylic acid, pelargonic acid, methoxyacetic acid, coconut oil fatty acid, palmitic acid, stearic acid, oleic acid, linoleic acid, lilunic acid, etc.
Examples include aromatic carboxylic acids such as benzoic acid, alkylbenzoic acid, alkylaminobenzoic acid, phenylacetic acid, halogenated benzoic acid, anisic acid, hendiylbenzoic acid, and natofeic acid, rosin, and water-added rosin.
次にエステル化合物＃の反応方法について述べる。Next, a reaction method for ester compound # will be described.
撹拌機４つロフラスコにアルコール成分（ａ）と酸成分
（ｂ）とを官能基比（ＯＨ／Ｃ００）Ｉ基孔）１．０５
〜１．８０の間で仕込み、さらに必要に応じて不活性反
応溶媒を入れ、窒素または炭酸ガス等の不活性ガスを吹
き込みながら、反応温度８０〜３００°Ｃ１好ましくは
１５０〜２６０°Ｃで理論量の９０％以上反応させる。Alcohol component (a) and acid component (b) were placed in a flask with four stirrers at a functional group ratio (OH/C00) of 1.05.
- 1.80 °C, and if necessary, add an inert reaction solvent, and while blowing an inert gas such as nitrogen or carbon dioxide, the reaction temperature is 80 to 300 °C, preferably 150 to 260 °C. React at least 90% of the amount.
反応は酸価のチエツクで追うのがよく、酸価はＩＯ以下
、好ましくは３以下である。The reaction is preferably followed by checking the acid value, which is IO or less, preferably 3 or less.
本発明に係る組成物は、上記エステル化合動画に、アク
リル酸もしくはメタクリル酸をエステル化反応せしめる
。反応は８０〜１２０ ”Ｃの温度で空気または不活性
ガスの存在下に、ハイドロキノンなどの重合禁止剤、硫
酸、ｐ−１−ルエンスルホン酸などの酸性触媒を用いて
行われる。酸価は２０以下とする。In the composition according to the present invention, the above-mentioned ester compound is subjected to an esterification reaction with acrylic acid or methacrylic acid. The reaction is carried out at a temperature of 80 to 120"C in the presence of air or an inert gas using a polymerization inhibitor such as hydroquinone and an acidic catalyst such as sulfuric acid or p-1-luenesulfonic acid. The acid number is 20 The following shall apply.
本発明に係る組成物においては、上記活性エネルギー線
硬化性樹脂組成物だけでなく、さらにラジカル重合性二
重結合を有するモノマー、例えば、メチル（メタ）アク
リレート、エチル（メタ）アクリレート、プロピル（メ
タ）アクリレート、アリル（メタ）アクリレート、ブチ
ル（メタ）アクリレート、アミル（メタ）アクリレート
、ヘキシル（メタ）アクリレート、オクチル（メタ）ア
クリレート、カプリル（メタ）アクリレート、デシル（
メタ）アクリレート、ラウリル（メタ）アクリレート、
ミリスチル（メタ）アクリレート、七チル（メタ）アク
リレート、ステアリル（メタ）アクリレート、ヘンシル
（メタ）アクリレート、アルキルフェノールのアルキレ
ンオイサイド付加物の（メタ）アクリレート、シクロヘ
キシル（メタ）アクリレート等の１官能七ツマ−が挙げ
られる。さらに２官能以上のモノマーとしてエチレング
リコールジ（メタ）アクリレート、ジエチレングリコー
ルジ（メタ）アクリレート、トリエチレングリコールジ
（メタ）アクリレート、ポリエチレングリコールジ（メ
タ）アクリレート、プロピレングリコールジ（メタ）ア
クリレート、ジプロピレングリコールジ（メタ）アクリ
レート、トリプロピレングリコールシ（メタ）アクリレ
ート、トリプロピレングリコールジ（メタ）アクリレー
ト、ブチレングリコールジ（メタ）アクリレート、ペン
チルグリコール（メタ）アクリレート、ネオペンチルグ
リコールシ（メタ）アクリレート、ヒドロキソピパリル
ヒＦロキシピハレートジ（メタ）アクリレート、ヘキサ
ンジオールジ（メタ）アクリレート、（ジ）グリセリン
トリ （メタ）アクリレート、ジグリセリンアルキレン
オキサイドテトラ（メタ）アクリレート、トリメチロー
ルプロパントリ （メタ）アクリレート、トリメチロー
ルプロパンアルキレンオキサイドトリ （メタ）アクリ
レート、ジトリメチロールプロパンテトラ（メタ）アク
リレート、ジトリメチロールプロパンアルキレンオキサ
イドテトラ（メタ）アクリレート、トリメチロールエタ
ントリ （メタ）アクリレート、ジトリメチロールエタ
ントリ（メタ）アクリレート、トリメチロールエタンア
ルキレンオキサイドトリ （メタ）アクリレート、ジト
リメチロールエタンアルキレンオキサイドテトロ（メタ
）アクリレート、テトラメチロールメタンテトラ（メタ
）アクリレート、ジベンタエリスリトールヘキサ（メタ
）アクリレート、ビスフェノールＡアルキレンオキサイ
ドジ（メタ）アクリレート、ビスフェノールＦアルキレ
ンオキサイビジ（メタ）アクリレート、ジヒドロキシヘ
ンセンアルキレンオキサイドジ（メタ）アクリレート、
トリヒドロキシベンゼンアルキレンオキサイドジ（メタ
）アクリレート、水添加ビスフェノールＡノ（メタ）ア
クリレート、水添加ビスフェノールＦジ（メタ）アクリ
レート、水添加ビスフェノールＡアルキレンオキサイド
付加体ジ（メタ）アクリレート、水添加ビスフェノール
Ｆアルキレンオキサイド付加体ジ（メタ）アクリレート
等が挙げられる。さらにその他にラクトン付加体のモノ
マーが挙げられる。In the composition according to the present invention, in addition to the active energy ray-curable resin composition, a monomer having a radically polymerizable double bond, such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, etc. ) acrylate, allyl (meth)acrylate, butyl (meth)acrylate, amyl (meth)acrylate, hexyl (meth)acrylate, octyl (meth)acrylate, caprylic (meth)acrylate, decyl (
meth)acrylate, lauryl(meth)acrylate,
Monofunctional 7-mers such as myristyl (meth)acrylate, heptyl (meth)acrylate, stearyl (meth)acrylate, hensyl (meth)acrylate, (meth)acrylate of alkylene oid adducts of alkylphenols, and cyclohexyl (meth)acrylate. can be mentioned. Furthermore, as monomers with more than two functionalities, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol Di(meth)acrylate, tripropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, pentyl glycol(meth)acrylate, neopentyl glycol di(meth)acrylate, hydroxopi Paryl hydroxypyhalate di(meth)acrylate, hexanediol di(meth)acrylate, (di)glycerin tri(meth)acrylate, diglycerin alkylene oxide tetra(meth)acrylate, trimethylolpropane tri(meth)acrylate, Trimethylolpropane alkylene oxide tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, ditrimethylolpropane alkylene oxide tetra(meth)acrylate, trimethylolethane tri(meth)acrylate, ditrimethylolethane tri(meth)acrylate, Methylolethane alkylene oxide tri(meth)acrylate, ditrimethylolethane alkylene oxide tetro(meth)acrylate, tetramethylolmethanetetra(meth)acrylate, diventaerythritol hexa(meth)acrylate, bisphenol A alkylene oxide di(meth)acrylate, bisphenol F alkylene oxybi di(meth)acrylate, dihydroxyhensen alkylene oxide di(meth)acrylate,
Trihydroxybenzene alkylene oxide di(meth)acrylate, hydrated bisphenol A no(meth)acrylate, hydrated bisphenol F di(meth)acrylate, hydrated bisphenol A alkylene oxide adduct di(meth)acrylate, hydrated bisphenol F alkylene Examples include oxide adduct di(meth)acrylate. In addition, monomers of lactone adducts may be mentioned.
すなわちポリエチレングリコールポリラクトネートジ（
メタ）アクリレート、ポリプロピレングリコールポリラ
クトネートジ（メタ）アクリレート、アルキレングリコ
ールボリラクトネートジ（メタ）アクリレート、グリセ
リンポリラクトネートトリ（メタ）アクリレート、ジグ
リセリンポリラクトネートテトラ（メタ）アクリレート
、トリメチロールプロパンポリラクトネートトリ （メ
タ）アクリレート、ジトリメチロールプロパンテトラ（
メタ）アクリレート、ペンタエリスリトールポリラクト
ネートテトラ（メタ）アクリレート、ジペンタエリスリ
トールポリラクト矛−トへキサアクリレート等の各ポリ
オールラクトネートポリアクリレートである。なお、上
記モノマーのラクトンはＴ−ブチロラクトン８−バレロ
ラクトン、ε−カプロラクトン等のエステルの官能基−
ＣＯ−０−を環内に含む化合物などと併用することがで
き、その併用割合はその目的に応して選択することがで
きるが、一般に本発明に係る活性工翠ルギー線硬化性樹
脂組成物の割合が２０重量％を下回ると本発明の効果が
減少する。That is, polyethylene glycol polylactonate di(
meth)acrylate, polypropylene glycol polylactonate di(meth)acrylate, alkylene glycol polylactonate di(meth)acrylate, glycerin polylactonate tri(meth)acrylate, diglycerin polylactonate tetra(meth)acrylate, trimethylolpropane Polylactonate tri(meth)acrylate, ditrimethylolpropane tetra(
These are various polyol lactonate polyacrylates such as meth)acrylate, pentaerythritol polylactonate tetra(meth)acrylate, and dipentaerythritol polylactone hexaacrylate. In addition, the lactone of the above monomer is a functional group of an ester such as T-butyrolactone, 8-valerolactone, and ε-caprolactone.
It can be used in combination with a compound containing CO-0- in the ring, and the proportion of the combination can be selected depending on the purpose, but in general, the activated hydrogen ray curable resin composition according to the present invention If the proportion is less than 20% by weight, the effects of the present invention will decrease.
また、活性エネルギー線が紫外線である場合には、ラジ
カル重合開始剤を添加する必要があり、例えばヘンツイ
ン、ヘンジインメチルエーテル、ヘンヅインエチルエー
テル、ヘンヅインイソブロビルエーテル、α−アクリル
ヘンゾイン等のヘンヅイン系増惑剤、ヘンシフエノン、
ｐ−メチルヘンシフエノン、ｐ−クロロヘンヅフエノン
、テトラクロロヘンシフエノン、０−ヘンソ１゛ル安息
香酸メチル、アセトフェノン等のアリールケトン系増感
剤、４，４−ビスジエチルアミノヘンヅフェノン、Ｐ−
ジメチルアミノ安息香酸イソアミル、ｐ−ジメチルアミ
ノアセトフェノン等のジアルキルアミノアリールケトン
系増感剤、チオキサントン、キサントンおよびそのハロ
ゲン置換体等の多環カルボニル系増感剤、イルガキュア
９０７（チバ・ガイギー社製増感剤・商品名）等が挙げ
られ、これらの単独もしくは適宜組み合せにより用いる
こともできる。In addition, when the active energy ray is ultraviolet rays, it is necessary to add a radical polymerization initiator, such as henzine, henzine methyl ether, henzine ethyl ether, henzine isobrobyl ether, α-acrylic henzine. Henzin type stimulants such as hensifenone,
Aryl ketone sensitizers such as p-methylhensiphenone, p-chlorohenduphenone, tetrachlorohenduphenone, 0-methylbenzoate, acetophenone, 4,4-bisdiethylaminohenduphenone ,P-
Isoamyl dimethylaminobenzoate, dialkylaminoarylketone sensitizers such as p-dimethylaminoacetophenone, polycyclic carbonyl sensitizers such as thioxanthone, xanthone and their halogen-substituted products, Irgacure 907 (sensitized by Ciba-Geigy) agent, trade name), etc., and these can be used alone or in an appropriate combination.
本発明において、印刷インキ組成物とするには上記樹脂
組成物中に顔料を分散させるが、この方法は特に限定さ
れることなく、三本ロール、ボールミル等の常法の分散
方法において行うことができる。また、有機、無機、体
質顔料の他に、必要に応じて可塑剤、界面活性剤、熱重
合禁止剤等を添加することができる。勿論顔料を使用し
ていないインキ組成物があってもよい。In the present invention, the pigment is dispersed in the resin composition to obtain the printing ink composition, but this method is not particularly limited and can be carried out by a conventional dispersion method such as a three-roll mill or a ball mill. can. In addition to organic, inorganic, and extender pigments, plasticizers, surfactants, thermal polymerization inhibitors, and the like can be added as necessary. Of course, there may be ink compositions that do not use pigments.
また、さらに本発明の効果を阻害しない範囲で他の樹脂
を併用することも可能である。Furthermore, it is also possible to use other resins in combination within a range that does not impede the effects of the present invention.
以下、具体例により本発明を説明する。例中の部は全て
重量部を示す。The present invention will be explained below using specific examples. All parts in the examples indicate parts by weight.
反応法
アルコール、酸成分およびキジロールを撹拌機付４つロ
フラスコに仕込み窒素ガス気流下で２００°Ｃで約１０
時間反応させ、酸価が５以下になったら脱溶媒し、次に
８０°Ｃまで冷却し、この温度で窒素ガス／空気の気流
下でヘンゼン、ハイドロキノン、ｐ−トルエンスルホン
酸、（メタ）アクリル酸と仕込み徐々に昇温して９０〜
１１５°Ｃの範囲で反応させ、酸価が２０以下になった
ところで脱溶媒しくみ出す。Reaction method Alcohol, acid component, and Kijirol were placed in four flasks equipped with a stirrer and heated at 200°C under a stream of nitrogen gas for about 10 minutes.
After reacting for several hours, when the acid value becomes 5 or less, the solvent is removed, then cooled to 80°C, and at this temperature, under a stream of nitrogen gas/air, Hensen, hydroquinone, p-toluenesulfonic acid, (meth)acrylic acid, Add acid and gradually raise the temperature to 90~
The reaction is carried out at a temperature of 115°C, and when the acid value becomes 20 or less, the solvent is removed.
次に上記樹脂とモノマー等を用い活性エネルギー線硬化
性被覆組成物を作製した。Next, an active energy ray-curable coating composition was prepared using the above resin, monomer, etc.
（注−１）表〜１中の略語は以下のとおりである。(Note-1) Abbreviations in Table 1 are as follows.
ＡＢＰＥ−４： ビスフェノールＡモルエチレンオキサ
イド付加体ジアクリレート
ＴＭＰＴＡ ： ｌ−リメチロールブロバントリア
クリレート
ＴＭＰＥＯＡ： ｔ−リメチロールブロバン３モルエ
チレンオキサイド付加体トリアク
リレート
光増感剤 ： ４．４−ビス（ジエチルアミノ）ベン
ゾフェノン／ベンゾフェノン
＝２１５
顔料 ：ファイネスレッドＦ２ＢＷ：東洋インキ
製造■製紅顔料
実施例１〜５および比較例１〜３
表−１に示す被覆組成物（印刷インキ）、すなわち、比
較例サンプル１〜３、実施例サンプル１〜５をＫＯＲＤ
ハイデルヘルグで印刷し、印刷時の非画線部への汚れ、
水中（注−２）を測定し、これを表−２に示す。ABPE-4: Bisphenol A mole ethylene oxide adduct diacrylate TMPTA: l-limethylolbroban triacrylate TMPEOA: t-limethylolbroban 3 mole ethylene oxide adduct triacrylate Photosensitizer: 4.4-bis(diethylamino) Benzophenone/benzophenone = 215 Pigment: Fines Red F2BW: Toyo Ink Manufacturing Red Pigment Examples 1 to 5 and Comparative Examples 1 to 3 Coating compositions (printing inks) shown in Table 1, i.e. Comparative Examples Samples 1 to 3 3. KORD example samples 1 to 5
When printing with Heidelherg, stains on non-printing areas during printing,
In water (Note-2) was measured and shown in Table-2.
表−２
（注−２）水中：印刷機に湿し水の量をコントロールす
る装置を設けて測定した。数字は湿し水の量を表す目盛
りで特に単位はない。Table 2 (Note 2) Underwater: Measured by installing a device to control the amount of dampening water in the printing press. The numbers are scales that represent the amount of dampening water, and there is no specific unit.
表中下限の数字は水の量を少なくしていった時の汚れの
発生した水の量を表す。また、上限の数字は水の量を多
くしていった場合にインキが乳化して転移不良になった
水の量を表す。The lower limit number in the table represents the amount of water in which stains were generated when the amount of water was decreased. Further, the upper limit number represents the amount of water at which the ink becomes emulsified and poor transfer occurs when the amount of water is increased.
実施例−５
上記実施例および比較例で印刷した被覆組成物を比較例
サンプル１〜２、実施例サンプル１〜３について８０Ｗ
／Ｃ１の強度を有する高圧水銀灯の下１０Ｃ１１のとこ
ろをコンベヤーにのせ１００ｍ７分照射した。また比較
例サンプル３、実施例サンプル４についてはカーテンビ
ーム型電子線照射装置を用い３Ｍｒ ａ ｄで照射した
。いずれも硬化していた。Example-5 The coating compositions printed in the above Examples and Comparative Examples were applied to Comparative Example Samples 1 to 2 and Example Samples 1 to 3 at 80W.
The lower part of the high-pressure mercury lamp having an intensity of /C1 was placed on a conveyor at 10C11 and irradiated for 100 m for 7 minutes. Further, Comparative Example Sample 3 and Example Sample 4 were irradiated at 3 Mr ad using a curtain beam type electron beam irradiation device. Both were hardened.
本発明の活性エネルギー線硬化性被覆組成物は従来知ら
れている被覆剤に比べ、実施例および比較例に示されて
いるように印刷効果がよく、活性エネルギー線効果性被
覆組成物の適用範囲を広めることができる。The active energy ray-curable coating composition of the present invention has a better printing effect than conventionally known coating materials, as shown in Examples and Comparative Examples, and the range of application of the active energy ray-curable coating composition is can be spread.
Claims (1)
）および（Ｃ）から選ばれる少くなくとも１種を用いて
なる水酸基過剰のアルキッド樹脂に（メタ）アクリル酸
と反応せしめてなることを特徴とする活性エネルギー線
硬化性樹脂組成物。 ▲数式、化学式、表等があります▼▲数式、化学式、表
等があります▼ （Ａ）（Ｂ） ▲数式、化学式、表等があります▼ （Ｃ） ２、請求項１の樹脂組成物、活性エネルギー線硬化性モ
ノマー、顔料及び必要に応じてラジカル重合開始剤を含
むことを特徴とする活性エネルギー線硬化性印刷インキ
組成物。[Claims] 1. The following compounds (A) and (B) as polyhydric alcohol components
1. An active energy ray-curable resin composition, characterized in that it is made by reacting an alkyd resin containing excess hydroxyl groups with (meth)acrylic acid using at least one selected from (C) and (C). ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (A) (B) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (C) 2. The resin composition of claim 1, activity An active energy ray curable printing ink composition comprising an energy ray curable monomer, a pigment, and, if necessary, a radical polymerization initiator.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2335563A JPH04202425A (en) | 1990-11-30 | 1990-11-30 | Actinc radiation-curable resin composition and printing ink composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2335563A JPH04202425A (en) | 1990-11-30 | 1990-11-30 | Actinc radiation-curable resin composition and printing ink composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04202425A true JPH04202425A (en) | 1992-07-23 |
Family
ID=18289982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2335563A Pending JPH04202425A (en) | 1990-11-30 | 1990-11-30 | Actinc radiation-curable resin composition and printing ink composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04202425A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016079211A (en) * | 2014-10-10 | 2016-05-16 | Ｄｉｃグラフィックス株式会社 | Active energy ray-curable offset ink composition |
| WO2018139328A1 (en) * | 2017-01-25 | 2018-08-02 | Dic株式会社 | Active-energy-ray-curable aqueous resin composition and undercoat agent for inorganic-material thin film |
-
1990
- 1990-11-30 JP JP2335563A patent/JPH04202425A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016079211A (en) * | 2014-10-10 | 2016-05-16 | Ｄｉｃグラフィックス株式会社 | Active energy ray-curable offset ink composition |
| WO2018139328A1 (en) * | 2017-01-25 | 2018-08-02 | Dic株式会社 | Active-energy-ray-curable aqueous resin composition and undercoat agent for inorganic-material thin film |
| JPWO2018139328A1 (en) * | 2017-01-25 | 2019-11-07 | Ｄｉｃ株式会社 | Active energy ray-curable aqueous resin composition and undercoat agent for inorganic material thin film |
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