JPH04283212A - Resin composition and printing ink composition - Google Patents
Resin composition and printing ink compositionInfo
- Publication number
- JPH04283212A JPH04283212A JP3070446A JP7044691A JPH04283212A JP H04283212 A JPH04283212 A JP H04283212A JP 3070446 A JP3070446 A JP 3070446A JP 7044691 A JP7044691 A JP 7044691A JP H04283212 A JPH04283212 A JP H04283212A
- Authority
- JP
- Japan
- Prior art keywords
- parts
- printing ink
- ink composition
- dipentaerythritol
- resin composition
- 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
- 238000007639 printing Methods 0.000 title claims abstract description 30
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 239000011342 resin composition Substances 0.000 title claims description 17
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 12
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 acrylic ester Chemical class 0.000 claims abstract description 11
- 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 claims abstract description 9
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims description 6
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- 238000004945 emulsification Methods 0.000 abstract description 6
- 239000000976 ink Substances 0.000 description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 6
- 239000012965 benzophenone Substances 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 238000010894 electron beam technology Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 239000004593 Epoxy Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- PASIEQDVKZQWRI-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol 3-hydroxy-2,2-dimethylpropanoic acid prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OCC(C)(C)CO.OCC(C)(C)C(O)=O PASIEQDVKZQWRI-UHFFFAOYSA-N 0.000 description 1
- CZZVAVMGKRNEAT-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)CO.OCC(C)(C)C(O)=O CZZVAVMGKRNEAT-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- WCAIBHQZNOQYAG-UHFFFAOYSA-N 3-hydroxy-2,2,5,5-tetramethylhexanoic acid Chemical compound CC(C)(C)CC(O)C(C)(C)C(O)=O WCAIBHQZNOQYAG-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- NPBCZIXJFJJSNL-UHFFFAOYSA-N C(C=C)(=O)OOCCC.C(C=C)(=O)OOCCC.C(C=C)(=O)OOCCC.C(O)C(CC)(CO)CO Chemical compound C(C=C)(=O)OOCCC.C(C=C)(=O)OOCCC.C(C=C)(=O)OOCCC.C(O)C(CC)(CO)CO NPBCZIXJFJJSNL-UHFFFAOYSA-N 0.000 description 1
- 229920004449 Halon® Polymers 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFSAUHSCHWRZKM-UHFFFAOYSA-N Padimate A Chemical compound CC(C)CCOC(=O)C1=CC=C(N(C)C)C=C1 OFSAUHSCHWRZKM-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- OTXQUGSUXRBUTC-UHFFFAOYSA-N butan-1-ol;toluene Chemical compound CCCCO.CC1=CC=CC=C1 OTXQUGSUXRBUTC-UHFFFAOYSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000003670 easy-to-clean Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000007644 letterpress printing Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/0073—Masks not provided for in groups H05K3/02 - H05K3/46, e.g. for photomechanical production of patterned surfaces
- H05K3/0076—Masks not provided for in groups H05K3/02 - H05K3/46, e.g. for photomechanical production of patterned surfaces characterised by the composition of the mask
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
【0001】0001
【産業上の利用分野】本発明は、樹脂組成物及び、特に
平版印刷で好適に使用し得る紫外線硬化性の印刷インキ
組成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a resin composition and an ultraviolet curable printing ink composition which can be suitably used in lithographic printing in particular.
【0002】0002
【従来の技術】近年、印刷インキの無溶剤化による公害
防止、急速硬化による生産性の向上、或いは、硬化皮膜
の物性改良を目的として紫外線硬化性印刷インキの開発
が盛んに進められている。紫外線硬化性印刷インキに関
しては、これまでに各種のものが提案されてきた。BACKGROUND OF THE INVENTION In recent years, the development of ultraviolet curable printing inks has been actively promoted for the purpose of preventing pollution by making printing inks solvent-free, improving productivity by rapid curing, and improving the physical properties of cured films. Various types of ultraviolet curable printing inks have been proposed so far.
【0003】0003
【発明が解決しようとする課題】従来の紫外線硬化性印
刷インキの多くには、希釈剤として、ジペンタエリスリ
トールとアクリル酸の反応物であるジペンタエリスリト
ールペンタアクリレートとジペンタエリスリトールヘキ
サアクリレートの混合物(ジペンタエリスリトールペン
タアクリレートとジペンタエリスリトールヘキサアクリ
レートの比率は、約40%〜60%:60%〜40%で
ある。)を使用している。これらの印刷インキは、紫外
線硬化速度については、満足し得るものが多いが、ジペ
ンタエリスリトールペンタアクリレート含有量が多いた
め、ジペンタエリスリトールペンタアクリレート中に含
まれるOH基の影響により湿し水により乳化し易いため
地汚れを起し易く問題となっている。Many conventional ultraviolet curable printing inks contain a mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate (a reaction product of dipentaerythritol and acrylic acid) as a diluent. The ratio of dipentaerythritol pentaacrylate to dipentaerythritol hexaacrylate is approximately 40%-60%:60%-40%). Most of these printing inks are satisfactory in terms of UV curing speed, but because they contain a high content of dipentaerythritol pentaacrylate, they are difficult to emulsify with dampening water due to the influence of the OH groups contained in dipentaerythritol pentaacrylate. Because it is easy to clean, it tends to cause staining, which is a problem.
【0004】0004
【課題を解決するための手段】本発明者らは、上記の課
題を改良するために鋭意研究の結果、耐湿し水乳化性に
優れた紫外線硬化性の印刷インキ組成物として特に有用
な樹脂組成物を見出し、本発明を完成するに至った。す
なわち、本発明は、[Means for Solving the Problems] As a result of intensive research in order to improve the above-mentioned problems, the present inventors have discovered a resin composition that is particularly useful as an ultraviolet curable printing ink composition with excellent moisture resistance and water emulsification properties. This discovery led to the completion of the present invention. That is, the present invention
【0005】1.ジペンタエリスリトールペンタアクリ
レートの含有量が20%以下であるジペンタエリスリト
ールとアクリル酸の反応物であるアクリル酸エステル(
A)と(A)成分以外のエチレン性不飽和基含有化合物
(B)を含むことを特徴とする樹脂組成物、2.ジペン
タエリスリトールペンタアクリレートの含有量が20%
以下であるジペンタエリスリトールとアクリル酸の反応
物であるアクリル酸エステル(B)を含むことを特徴と
する印刷インキ組成物、
3.第1項記載の樹脂組成物の硬化物、4.第2項記載
の印刷インキ組成物の硬化物に関する。1. Acrylic acid ester, which is a reaction product of dipentaerythritol and acrylic acid, with a content of dipentaerythritol pentaacrylate of 20% or less (
A resin composition characterized by containing A) and an ethylenically unsaturated group-containing compound (B) other than the component (A); 2. Dipentaerythritol pentaacrylate content is 20%
3. A printing ink composition characterized by containing an acrylic ester (B) which is a reaction product of dipentaerythritol and acrylic acid as follows; 3. 4. A cured product of the resin composition according to item 1. 2. A cured product of the printing ink composition according to item 2.
【0006】本発明に使用されるジペンタエリスリトー
ルペンタアクリレートの含有量が20%以下であるジペ
ンタエリスリトールとアクリル酸の反応物であるエクリ
ル酸エステル(A)は次のようにして製造する。即ちジ
ペンタエリスリトールの水酸基1化学当量に対して、ア
クリル酸を通常1.1〜5.0化学当量好ましくは、1
.5〜2.5化学当量反応させて製造する。製造に際し
ては反応を促進させるために、エステル化触媒(例えば
、p−トルエンスルホンサン酸、硫酸及びメタンスルホ
ン酸等)を使用するのが好ましい。エステル化触媒の使
用量は、使用するアクリル酸に対して、通常0.1〜1
5モル%好ましくは1〜6モル%である。又、反応中の
重合を防止するためにハイドロキノン、フェノチアジン
等の重合禁止剤を使用するのが好ましい。反応温度は7
0〜150℃が好ましく、特に好ましくは80〜130
℃である。反応の溶媒としては、ベンゼン、トルエン、
シクロヘキサン、n−ヘキサン等の非反応性の溶媒を使
用するのが好ましい。[0006] The ecrylic ester (A), which is a reaction product of dipentaerythritol and acrylic acid and has a content of dipentaerythritol pentaacrylate of 20% or less, used in the present invention is produced as follows. That is, for 1 chemical equivalent of hydroxyl group of dipentaerythritol, 1.1 to 5.0 chemical equivalents of acrylic acid, preferably 1 chemical equivalent of acrylic acid, is used.
.. It is produced by reacting 5 to 2.5 chemical equivalents. In order to accelerate the reaction during production, it is preferable to use an esterification catalyst (eg, p-toluenesulfonic acid, sulfuric acid, methanesulfonic acid, etc.). The amount of the esterification catalyst used is usually 0.1 to 1 based on the acrylic acid used.
It is 5 mol%, preferably 1 to 6 mol%. Further, in order to prevent polymerization during the reaction, it is preferable to use a polymerization inhibitor such as hydroquinone or phenothiazine. The reaction temperature is 7
0 to 150°C is preferable, particularly preferably 80 to 130°C.
It is ℃. As a solvent for the reaction, benzene, toluene,
Preferably, non-reactive solvents such as cyclohexane and n-hexane are used.
【0007】本発明では、(A)成分以外のエチレン性
不飽和基含有化合物(B)を使用する。(B)成分の具
体例としては、好ましくは(メタ)アクリロイル基を有
する化合物が挙げられ、例えば、ヒドロキシピバリン酸
ネオペンチルグリコールジ(メタ)アクリレート、トリ
シクロデカンジメチロールジ(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In the present invention, an ethylenically unsaturated group-containing compound (B) other than component (A) is used. Specific examples of component (B) preferably include compounds having a (meth)acryloyl group, such as neopentyl hydroxypivalic acid glycol di(meth)acrylate, tricyclodecane dimethylol di(meth)acrylate, polyethylene Glycol di(meth)acrylate
【000
8】000
8]
【0009】トリメチロールプロパントリプロポキシト
リ(メタ)アクリレート、トリメチロールプロパントリ
エトキシトリ(メタ)アクリレート、ペンタエリスリト
ールテトラプロポキシテトラ(メタ)アクリレート、ビ
スフェノールAのポリエトキシジ(メタ)アクリレート
、ビスフェノールFのポリエトキシジ(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ポリプロポキシテト
ラ(メタ)アクリレート、一分子内にアクリロイル基を
有するウレタン変性(メタ)アクリレート若しくは、エ
ポキシ(メタ)アクリレート、多価アルコールと多塩基
酸からなるポリエステルの(メタ)アクリサート、ビス
フェノール型、ノボラック型或いは、脂環型のエポキシ
樹脂の(メタ)アクリレートであるエポキシ樹脂のエポ
キシ(メタ)アクリレート、2−ヒドロキシエチル(メ
タ)アクリレート、ペンタエリスリトールトリ(メタ)
アクリレート等のヒドロキシル基とイソシアネート化合
物との反応物であるポリウレタン(メタ)アクリレート
、アルキッド(メタ)アクリレート等を単独若しくは混
合して使用することができる。特に好ましい(B)成分
としては、ジトリメチロールプパンテトラアクリレート
、トリメチロールプロパントリプロポキシトリアクリレ
ート、ヒドロキシピバリン酸ネオペンチルグリコールジ
アクリレート、前記(1)式の化合物トリシクロデカン
ジメチロールジアクリレート、ビスフェノールAのポリ
エトキシジアクリレート、エポキシアクリレート、ポリ
エステルアクリレート等を挙げることができる。Trimethylolpropane tripropoxytri(meth)acrylate, trimethylolpropanetriethoxytri(meth)acrylate, pentaerythritol tetrapropoxytetra(meth)acrylate, polyethoxydi(meth)acrylate of bisphenol A, polyethoxydi(meth)acrylate of bisphenol F ) acrylate, ditrimethylolpropane tetra(meth)acrylate, ditrimethylolpropane polypropoxytetra(meth)acrylate, urethane-modified (meth)acrylate or epoxy(meth)acrylate having an acryloyl group in one molecule, polyhydric alcohol and (meth)acrylate of polyester consisting of basic acid, epoxy (meth)acrylate of epoxy resin which is (meth)acrylate of bisphenol type, novolac type or alicyclic type epoxy resin, 2-hydroxyethyl (meth)acrylate, penta Erythritoltri (meth)
Polyurethane (meth)acrylates, alkyd (meth)acrylates, etc., which are reaction products of hydroxyl groups such as acrylates and isocyanate compounds, can be used alone or in combination. Particularly preferred component (B) is ditrimethylolpropane tetraacrylate, trimethylolpropane tripropoxy triacrylate, neopentyl glycol diacrylate hydroxypivalate, tricyclodecane dimethylol diacrylate compound of formula (1), bisphenol A Examples include polyethoxy diacrylate, epoxy acrylate, and polyester acrylate.
【0010】本発明による樹脂組成物を光硬化させる際
には、光エネルギーを吸収してラジカルを発生させる光
重合開始剤(C)を併用することが好ましい。その光重
合開始剤(C)としては、例えば、2,4−ジエチルチ
オキサントン、ベンゾフェノン、イソプロピルチオキサ
ントン、2−ヒドロキシ−2−メチルプロピオフェノン
、ベンジルジメチルケタノール、1−ヒドロキシシクロ
ヘキシルフェニルケトン、イルガキュア−907(チバ
・ガイギー社製、光重合開始剤)、0−ベンゾイル安息
香酸メチルエステル、p−ジメチルアミノ安息香酸イソ
アミルエステル、p−ジメチルアミノアセトフェノン、
p−ジメチルアミノベンズアルデヒド等が挙げられる。
かかる光重合開始剤は1種或いは2種以上を混合して使
用することができる。好ましい光重合開始剤(C)とし
ては、ベンゾフェノン、2,4−ジエチルチオキサント
ン、2−ヒドロキシ−2−メチルプロピオフェノン、ベ
ンジルジメチルケタール、1−ヒドロキシシクロヘキシ
ルフェニルケトン、イルガキュア−907、p−ジメチ
ルアミノ安息香酸エチルエステル等が挙げられる。本発
明の樹脂組成物は電子線照射により硬化させる場合は光
重合開始剤(C)を配合する必要はない。When photocuring the resin composition of the present invention, it is preferable to use a photopolymerization initiator (C) that absorbs light energy and generates radicals. Examples of the photopolymerization initiator (C) include 2,4-diethylthioxanthone, benzophenone, isopropylthioxanthone, 2-hydroxy-2-methylpropiophenone, benzyldimethylketanol, 1-hydroxycyclohexyl phenylketone, Irgacure- 907 (manufactured by Ciba Geigy, photopolymerization initiator), 0-benzoylbenzoic acid methyl ester, p-dimethylaminobenzoic acid isoamyl ester, p-dimethylaminoacetophenone,
Examples include p-dimethylaminobenzaldehyde. Such photopolymerization initiators can be used alone or in combination of two or more. Preferred photoinitiators (C) include benzophenone, 2,4-diethylthioxanthone, 2-hydroxy-2-methylpropiophenone, benzyl dimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, Irgacure-907, p-dimethylamino Examples include benzoic acid ethyl ester. When the resin composition of the present invention is cured by electron beam irradiation, there is no need to add a photopolymerization initiator (C).
【0011】本発明の樹脂組成物及び印刷インキ組成物
は、前記アクリル酸エステル(A)100重量部に対し
て、前記エチレン性不飽和基含有化合物(B)を10〜
900重量部使用するのが好ましく、50〜500重量
部、使用するのが特に好ましい。光重合開始剤(C)の
使用量は、成分(A)+成分(B)の総量100重量部
に対して、0〜30重量部が好ましく、2〜25重量部
の割合で混合して形成したものがより好ましい。The resin composition and printing ink composition of the present invention contain 10 to 10 parts by weight of the ethylenically unsaturated group-containing compound (B) per 100 parts by weight of the acrylic ester (A).
Preferably, 900 parts by weight are used, particularly preferably 50 to 500 parts by weight. The amount of photopolymerization initiator (C) used is preferably 0 to 30 parts by weight, based on 100 parts by weight of the total amount of component (A) + component (B), and is formed by mixing at a ratio of 2 to 25 parts by weight. It is more preferable.
【0012】本発明の樹脂組成物および印刷インキ組成
物には必要により、樹脂類、例えば、ジアリルフタレー
ル樹脂(大阪曹達(株)製、ダイソーダップA)、石油
樹脂(例えば、東燃石油化学(株)製、エスコレッツ、
三井石油化学(株)製、ハイレッツ、ペトロジー、タッ
クエース、日本ゼオン(株)製、クイントン、日本石油
化学(株)、ネオポリマー、東邦石油(株)製、ハイレ
ジン、荒川化学(株)製、アルコン、東洋ソーダ製、ペ
トコール等)、環状ケトン樹脂(例えば、日立化成(株
)製、ハイラック80、110H、111、222、本
州化学(株)製、ハロン80、110等)、芳香族炭化
水素ホルムアルデヒド樹脂(例えば、三菱ガス化学(株
)、ニカノール、松下電工(株)製、ナショナルキシレ
ン等)、天然樹脂変性フェノール樹脂、アクリル樹脂、
スチルポリマー等を使用することができる。又、溶剤類
、例えば、メチルエチルケトン、酢酸ブチル、トルエン
n−ブタノール、ブチルセロソルブアセテート、カルビ
トールアセテート、ソルベントナフサ等を使用すること
ができる。さらに添加剤類、例えば、製造時あるいは、
貯蔵中の暗反応によるゲル化防止の為の熱重合禁止剤(
例えば、ハイドロキノン、p−ベンゾキノン、フェノチ
アジン、t−ブチルカテコール等)、有機・顔料、無機
・顔料、シランカップリング剤、レベリング剤、スリッ
プ剤、酸化防止剤、光安定剤、帯電防止剤等などを使用
することができる。本発明の樹脂組成物は各成分を均一
に混合することにより得ることができる。The resin composition and printing ink composition of the present invention may optionally contain resins such as diallylphthaler resin (Daiso Dapp A manufactured by Osaka Soda Co., Ltd.), petroleum resins (such as Tonen Petrochemical Co., Ltd.) Co., Ltd., Escolettes,
Manufactured by Mitsui Petrochemical Co., Ltd., Hilets, Petrogy, Tac Ace, Nippon Zeon Co., Ltd., Quinton, Nippon Petrochemical Co., Ltd., Neopolymer, Toho Oil Co., Ltd., Hi-Resin, Arakawa Chemical Co., Ltd., Alcon, Toyo Soda, Petcol, etc.), cyclic ketone resins (e.g., Hitachi Chemical Co., Ltd., Hilac 80, 110H, 111, 222, Honshu Chemical Co., Ltd., Halon 80, 110, etc.), aromatic carbonization Hydrogen formaldehyde resin (e.g., Mitsubishi Gas Chemical Co., Ltd., Nicanol, Matsushita Electric Works, Ltd., National Xylene, etc.), natural resin-modified phenolic resin, acrylic resin,
Still polymers and the like can be used. Also, solvents such as methyl ethyl ketone, butyl acetate, toluene n-butanol, butyl cellosolve acetate, carbitol acetate, solvent naphtha, etc. can be used. Additionally, additives may be added, e.g. during manufacturing or
Thermal polymerization inhibitor to prevent gelation due to dark reaction during storage (
For example, hydroquinone, p-benzoquinone, phenothiazine, t-butylcatechol, etc.), organic pigments, inorganic pigments, silane coupling agents, leveling agents, slip agents, antioxidants, light stabilizers, antistatic agents, etc. can be used. The resin composition of the present invention can be obtained by uniformly mixing each component.
【0013】本発明の樹脂組成物は、特に印刷インキ組
成物として有用であるが、その他に紙のつや出しコーテ
ィング剤、ソルダーレジスト、写真現像型ソルダーレジ
スト、ハードコート剤、保護コーティング剤等としても
有用である。本発明の樹脂組成物の硬化物は常法により
電子線又は紫外線を照射して硬化させて得ることができ
る。特に印刷インキ組成物は、例えば、平版印刷(オフ
セット印刷)、凸版印刷、スクリーン印刷、枚葉印刷等
の手段により、紙、プラスチック、金属、ガラス、セラ
ミック、木、石等に印刷され、その後常法により、電子
線又は紫外線を照射して硬化する。The resin composition of the present invention is particularly useful as a printing ink composition, but is also useful as a gloss coating agent for paper, a solder resist, a photo-developable solder resist, a hard coat agent, a protective coating agent, etc. It is. The cured product of the resin composition of the present invention can be obtained by curing the resin composition by irradiating it with electron beams or ultraviolet rays in a conventional manner. In particular, the printing ink composition is printed on paper, plastic, metal, glass, ceramic, wood, stone, etc. by means such as lithographic printing (offset printing), letterpress printing, screen printing, sheet-fed printing, etc., and then It is cured by irradiation with electron beams or ultraviolet rays.
【0014】[0014]
【実施例】次に、本発明を実施例と比較例により具体的
に説明する。実施例中の部は、重量部を表す。アクリル
酸エステル(A)の合成例
合成例1
ジペンタエリスリトール254部、アクリル酸735部
、硫酸24部、ハイドロキノン7部、ベンゼン600部
、シクロヘキサン150部を仕込み、加熱し、生成水は
、溶剤と共に蒸留し、凝縮させ分離器で水が108部生
成した時点で冷却した。反応温度は、85〜95℃であ
った。反応混合物をベンゼン1200部及びシクロヘキ
サン300部に溶解し、20%苛性ソーダ水溶液で中和
した後、20%塩化ナトリウム水溶液500部で3回洗
浄し、メトキノン0.29部を加える。溶剤を減圧留去
して、液体520部を得た。粘度(25℃)80ポイズ
であった。生成物中のジペンタエリスリトールペンタア
クリレートは10%であった。(液体クロマトグラフィ
ー分析による。)[Examples] Next, the present invention will be specifically explained with reference to Examples and Comparative Examples. Parts in the examples represent parts by weight. Synthesis example of acrylic acid ester (A) Synthesis example 1 254 parts of dipentaerythritol, 735 parts of acrylic acid, 24 parts of sulfuric acid, 7 parts of hydroquinone, 600 parts of benzene, and 150 parts of cyclohexane were charged and heated, and the produced water was mixed with the solvent. It was distilled, condensed and cooled when 108 parts of water was produced in the separator. The reaction temperature was 85-95°C. The reaction mixture is dissolved in 1200 parts of benzene and 300 parts of cyclohexane, neutralized with 20% aqueous sodium hydroxide solution, washed three times with 500 parts of 20% aqueous sodium chloride solution, and 0.29 part of methoquinone is added. The solvent was distilled off under reduced pressure to obtain 520 parts of liquid. The viscosity (25°C) was 80 poise. Dipentaerythritol pentaacrylate in the product was 10%. (Based on liquid chromatography analysis.)
【0015】実施例1
ネオペンチグリコール208部、テレフタル酸166部
、トルエン40部、p−トルエンスルホン酸0.9部、
亜リン酸0.9部を仕込み窒素ガスを吹込みながら18
0℃まで加熱し、6時間反応させる。反応は、酸価10
以下になるまで継続する。次いで、アクリル酸142部
、シクロヘキサン54部、ハイドロキノン0.1部を加
え、100℃で反応を続け、酸価25以下になるまで継
続して後、減圧下でトルエン、シクロヘキサンを除去す
る。次いで、ヒドロキシピバリン酸ネオペンチルグリコ
ールジアクリサート(日本化薬(株)製、KATARA
DMANDA)100部を加えてポリエステルアクリレ
ートを得た。上記で得られたポリエステルアクリレート
(B)35部、合成例1で得たアクリル酸エステル(A
)35部、メチルハイドロキノン0.1部「Brigh
t Red」(東洋インキ(株)製)16.5部、ベン
ゾフェノン7部、p−ジメチルアミノ)安息香酸エチル
エステル7部を混合し、3本ロールミルで練肉し、印刷
インキ組成物を得た。Example 1 208 parts of neopentyglycol, 166 parts of terephthalic acid, 40 parts of toluene, 0.9 parts of p-toluenesulfonic acid,
18 while adding 0.9 part of phosphorous acid and blowing in nitrogen gas.
Heat to 0°C and react for 6 hours. The reaction takes place at an acid value of 10
Continue until below. Next, 142 parts of acrylic acid, 54 parts of cyclohexane, and 0.1 part of hydroquinone are added, and the reaction is continued at 100°C until the acid value becomes 25 or less, and then toluene and cyclohexane are removed under reduced pressure. Next, hydroxypivalic acid neopentyl glycol diacrysate (manufactured by Nippon Kayaku Co., Ltd., KATARA)
DMANDA) was added to obtain polyester acrylate. 35 parts of polyester acrylate (B) obtained above, acrylic ester (A) obtained in Synthesis Example 1
) 35 parts, 0.1 part of methylhydroquinone
t Red" (manufactured by Toyo Ink Co., Ltd.), 7 parts of benzophenone, and 7 parts of p-dimethylamino)benzoic acid ethyl ester were mixed and kneaded in a three-roll mill to obtain a printing ink composition. .
【0016】実施例2
合成例1で得たアクリル酸エステル(A)30部、ジト
リメチロールプロパンテトラアクリレート(B)25部
、「ネオポリマー120」(日本石油化学(株)製、石
油樹脂)13部、メチルハイドロキノン0.1部を加熱
し溶解し、次いで冷却後、「Bright Red」1
8部、ベンゾフェノン7部、p−ジメチルアミノ安息香
酸エチルエステル7部を混合し、3本ロールミルで練肉
し印刷インキ組成物を得た。Example 2 30 parts of acrylic ester (A) obtained in Synthesis Example 1, 25 parts of ditrimethylolpropane tetraacrylate (B), 13 parts of "Neopolymer 120" (manufactured by Nippon Petrochemical Co., Ltd., petroleum resin) 1 part of "Bright Red" by heating and dissolving 0.1 part of methylhydroquinone, and then cooling.
8 parts of benzophenone, 7 parts of benzophenone, and 7 parts of p-dimethylaminobenzoic acid ethyl ester were mixed and milled using a three-roll mill to obtain a printing ink composition.
【0017】実施例3
実施例1中ベンゾフェノン及びp−ジメチルアミノ安息
香酸エチルエステルをのぞき、実施例1と同様にして、
印刷インキ組成物を得た。Example 3 The same procedure as in Example 1 was carried out except for benzophenone and p-dimethylaminobenzoic acid ethyl ester in Example 1.
A printing ink composition was obtained.
【0018】比較例1
実施例1中アクリル酸エステル(A)をKAYARAD
DPHA(日本化薬(株)製、ジペンタエリスリトー
ルヘキサアクリレート44%、ジペンタエリスリトール
ペンタアクリレート30%を含有するポリアクリレート
)35部に変えた以外は実施例1と同様にして、印刷イ
ンキ組成物を得た。前記各例中のインキを用い、下記の
各項目について評価テストを行い、その結果を表−1に
示した。Comparative Example 1 The acrylic ester (A) in Example 1 was replaced with KAYARAD.
A printing ink composition was prepared in the same manner as in Example 1, except that 35 parts of DPHA (manufactured by Nippon Kayaku Co., Ltd., polyacrylate containing 44% dipentaerythritol hexaacrylate and 30% dipentaerythritol pentaacrylate) was used. I got it. Evaluation tests were conducted on the following items using the inks in each of the above examples, and the results are shown in Table 1.
【0019】(1)耐乳化性
明製作所製RI−2型印刷試験機の練りロール上のイン
キに湿し水をたらし、乳化状能を観察した。
評価
不良 ───── 乳化しているやや不良
───── やや乳化している良 ─
─── 全く乳化せず(2)硬化性
RI−2型印刷試験機で紙上にインキの膜厚が3μとな
るように展色後、実施例1、2、比較例1については、
高圧水銀灯(80w/cm、1灯)下8cmの所を通過
させ、指触乾燥に要する照射量(mJ/cm 2 )
を測定した。
実施例3については、電子線照射機(ESI社製、電圧
175V)で電子線を照射し、指触乾燥に要する照射量
(メガラッド)を測定した。
(3)洗い油洗浄性
灯油とインキを重量比5:1の割合で混合し、その相溶
性を洗浄性のめやすとした。
評価
不良 ───── 溶解せず分離している
やや不良 ───── 一部が完全に溶解せず分離
している
良 ──── 均一に溶解し分散して
いる。(1) Emulsification Resistance Dampening water was poured onto the ink on the mixing roll of a RI-2 printing tester manufactured by Mei Seisakusho, and the emulsification ability was observed. Poor evaluation ───── Emulsified, slightly poor ───── Slightly emulsified, good ─
─── Not emulsified at all (2) Curing After spreading the ink on paper using an RI-2 printing tester so that the ink film thickness was 3 μm, for Examples 1 and 2 and Comparative Example 1,
The amount of irradiation required to be dry to the touch (mJ/cm 2 ) when passed through a point 8 cm below a high-pressure mercury lamp (80 W/cm, 1 lamp)
was measured. For Example 3, an electron beam was irradiated with an electron beam irradiator (manufactured by ESI, voltage 175 V), and the irradiation amount (megarad) required for dryness to the touch was measured. (3) Washing oil detergency Kerosene and ink were mixed at a weight ratio of 5:1, and their compatibility was taken as a measure of detergency. Poor evaluation --- Slightly poor, with no dissolution and separation --- Good, with a portion not completely dissolved and separation --- Uniformly dissolved and dispersed.
【0020】
表 1
実 施 例
比 較 例
1 2
3 1
耐乳化性 良
良 良
不良 インキの硬化性 20mJ/c
m2 25mJ/cm2 1メカ゛ラット゛
23mJ/cm 2 洗い油洗浄性
良 良
良 やや不良[0020]
Table 1
Example
Comparison example
1 2
3 1
Good emulsification resistance
Good Good
Defective Ink hardenability 20mJ/c
m2 25mJ/cm2 1 mechanism rat
23mJ/cm 2 Washing oil detergency
Good Good
Good Slightly poor
【0021】[0021]
【発明の効果】本発明の樹脂組成物及び印刷インキ組成
物は、特に耐湿し水乳化性、洗浄性、硬化性に優れ、特
に平版印刷インキに適する。本発明の樹脂組成物及び印
刷インキ組成物は、顔料に対するぬれ性、基材に対する
密着性にも優れかつ低毒性である。EFFECTS OF THE INVENTION The resin composition and printing ink composition of the present invention are particularly excellent in moisture resistance, water emulsifying properties, washability, and curing properties, and are particularly suitable for use as lithographic printing inks. The resin composition and printing ink composition of the present invention have excellent wettability to pigments, excellent adhesion to substrates, and low toxicity.
Claims (4)
トの含有量が20%以下であるジペンタエリスリトール
とアクリル酸の反応物であるアクリル酸エステル(A)
と(A)成分以外のエチレン性不飽和基含有化合物(B
)を含むことを特徴とする樹脂組成物。Claim 1: An acrylic ester (A) which is a reaction product of dipentaerythritol and acrylic acid and has a dipentaerythritol pentaacrylate content of 20% or less.
and an ethylenically unsaturated group-containing compound other than component (A) (B
) A resin composition comprising:
レートの含有量が20%以下であるジペンタエリスリト
ールとアクリル酸の反応物であるアクリル酸エステル(
A)と(A)成分以外のエチレン性不飽和基含有化合物
(B)を含むことを特徴とする印刷インキ組成物。2. Acrylic acid ester (which is a reaction product of dipentaerythritol and acrylic acid) containing 20% or less of dipentaerythritol pentaacrylate (
A printing ink composition comprising A) and an ethylenically unsaturated group-containing compound (B) other than component (A).
。3. A cured product of the resin composition according to claim 1.
硬化物。4. A cured product of the printing ink composition according to claim 2.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3070446A JPH04283212A (en) | 1991-03-12 | 1991-03-12 | Resin composition and printing ink composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3070446A JPH04283212A (en) | 1991-03-12 | 1991-03-12 | Resin composition and printing ink composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH04283212A true JPH04283212A (en) | 1992-10-08 |
Family
ID=13431736
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3070446A Pending JPH04283212A (en) | 1991-03-12 | 1991-03-12 | Resin composition and printing ink composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH04283212A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017090663A1 (en) * | 2015-11-25 | 2017-06-01 | 東レ株式会社 | Lithographic ink |
-
1991
- 1991-03-12 JP JP3070446A patent/JPH04283212A/en active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017090663A1 (en) * | 2015-11-25 | 2017-06-01 | 東レ株式会社 | Lithographic ink |
JPWO2017090663A1 (en) * | 2015-11-25 | 2018-02-15 | 東レ株式会社 | Ink for lithographic printing |
KR20180084760A (en) * | 2015-11-25 | 2018-07-25 | 도레이 카부시키가이샤 | Ink for flatbed printing |
US11161991B2 (en) | 2015-11-25 | 2021-11-02 | Toray Industries, Inc. | Lithographic ink |
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