JPH0431422A - Actinic radiation curable resin composition - Google Patents
Actinic radiation curable resin compositionInfo
- Publication number
- JPH0431422A JPH0431422A JP2135775A JP13577590A JPH0431422A JP H0431422 A JPH0431422 A JP H0431422A JP 2135775 A JP2135775 A JP 2135775A JP 13577590 A JP13577590 A JP 13577590A JP H0431422 A JPH0431422 A JP H0431422A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylate
- molecule
- resin composition
- acid
- 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 description 20
- 230000005855 radiation Effects 0.000 title description 2
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 25
- 229920005989 resin Polymers 0.000 claims abstract description 20
- 239000011347 resin Substances 0.000 claims abstract description 20
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 7
- 229920005862 polyol Polymers 0.000 claims abstract description 5
- 150000003077 polyols Chemical class 0.000 claims abstract description 4
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims abstract 3
- -1 isocyanate compound Chemical class 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 11
- 239000012948 isocyanate Substances 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 abstract description 4
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 abstract description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 abstract 1
- 238000005452 bending Methods 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 37
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- 238000005299 abrasion Methods 0.000 description 7
- 239000003973 paint Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000000976 ink Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- RAADBCJYJHQQBI-UHFFFAOYSA-N 2-sulfoterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(S(O)(=O)=O)=C1 RAADBCJYJHQQBI-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
- 239000004925 Acrylic resin Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical compound OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 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
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000012756 surface treatment agent Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- FGOSBCXOMBLILW-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 FGOSBCXOMBLILW-UHFFFAOYSA-N 0.000 description 1
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- COTZVJGHVRNXLY-UHFFFAOYSA-N 1,1-diisocyanatoheptane Chemical compound CCCCCCC(N=C=O)N=C=O COTZVJGHVRNXLY-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- MMRZOPJUBLVLTI-UHFFFAOYSA-N 1,3-dichloro-2,2-dimethylpropane-1,3-diol Chemical compound ClC(O)C(C)(C(O)Cl)C MMRZOPJUBLVLTI-UHFFFAOYSA-N 0.000 description 1
- HJXBSJQKCRHYPT-UHFFFAOYSA-N 1,4-bis(hydroxymethyl)cyclohexane-1,4-diol cyclohexane Chemical compound C(O)C1(CCC(CC1)(O)CO)O.C1CCCCC1 HJXBSJQKCRHYPT-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- YZTJKOLMWJNVFH-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O YZTJKOLMWJNVFH-UHFFFAOYSA-N 0.000 description 1
- XIRDTMSOGDWMOX-UHFFFAOYSA-N 3,4,5,6-tetrabromophthalic acid Chemical compound OC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O XIRDTMSOGDWMOX-UHFFFAOYSA-N 0.000 description 1
- CTJFNNZDSZIGOM-UHFFFAOYSA-N 3-methylcyclohex-2-ene-1,1,2-tricarboxylic acid Chemical compound CC1=C(C(O)=O)C(C(O)=O)(C(O)=O)CCC1 CTJFNNZDSZIGOM-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical class C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- WNKQDGLSQUASME-UHFFFAOYSA-N 4-sulfophthalic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1C(O)=O WNKQDGLSQUASME-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- MWMBMDKWXVQCHY-UHFFFAOYSA-N C.OC(=O)C=C Chemical compound C.OC(=O)C=C MWMBMDKWXVQCHY-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004606 Fillers/Extenders Substances 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Natural products OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- HXTLWOZJMYIANK-UHFFFAOYSA-N butyl acetate;methanol Chemical compound OC.CCCCOC(C)=O HXTLWOZJMYIANK-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical compound [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- UFGZSIPAQKLCGR-UHFFFAOYSA-N chromium carbide Chemical compound [Cr]#C[Cr]C#[Cr] UFGZSIPAQKLCGR-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- PIJPYDMVFNTHIP-UHFFFAOYSA-L lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000000463 material Substances 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
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing 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
- 229910003470 tongbaite Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は新規にして有用なる活性エネルギー線硬化型樹
脂組成物に関する。さらに詳細には、本発明は必須の有
効成分として、特定のウレタンアクリレートを含んで成
る、とりわけ硬化性、樹脂硬化後の耐擦傷性、耐汚染性
、屈曲性ならびに耐候性にすぐれる活性エネルギー線硬
化型樹脂組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel and useful active energy ray-curable resin composition. More specifically, the present invention provides active energy rays containing a specific urethane acrylate as an essential active ingredient, which has excellent curability, scratch resistance after resin curing, stain resistance, flexibility, and weather resistance. The present invention relates to a curable resin composition.
そして本発明の樹脂組成物は、一般塗料や表面処理剤な
どとして、紙、木工製品、プラスチック、金属類などを
はじめ、その他の各種有機ないしは無機材料用に極めて
有用なものである。The resin composition of the present invention is extremely useful as a general paint or surface treatment agent for paper, wood products, plastics, metals, and other various organic or inorganic materials.
近年、活性エネルギー線硬化型樹脂は、特に塗料などの
、いわゆる表面処理剤をはじめ広く利用されるようにな
った。これは従来の硬化方法と比べて、格段に速い硬化
性と、非加熱硬化と、無溶剤化とが可能となり、ライン
の省スペース化や、硬化に必要なエネルギー効率がよい
ことなどといった多くの利点を持っている為である。In recent years, active energy ray-curable resins have come to be widely used, especially as so-called surface treatment agents, such as paints. Compared to conventional curing methods, this method enables much faster curing, non-thermal curing, and no solvent, and has many benefits such as space saving on the line and energy efficiency required for curing. This is because it has advantages.
この種の活性エネルギー線硬化型樹脂としては、これま
でにも、α、β−エチレン性不飽和二重結合を含有して
なる樹脂系が使用されており、ポリエステル（メタ）ア
クリレート、不飽和ポリエステル、ポリエーテル（メタ
ンアクリレートまたはポリウレタン（メタ）アクリレー
トなどが代表例として挙げられる。As this type of active energy ray-curable resin, resin systems containing α, β-ethylenically unsaturated double bonds have been used, including polyester (meth)acrylate, unsaturated polyester , polyether (methane acrylate or polyurethane (meth)acrylate) are typical examples.
ところで、これまでの活性エネルギー線硬化型樹脂系は
、概して、硬化膜が硬いものの設計に対しては向いてお
り、代表例としてハードフートの如き表面硬度が大変に
高く、耐擦傷性にすぐれるようなものが開発されている
。By the way, conventional active energy ray-curable resin systems are generally suitable for designing products with hard cured films, and a typical example is hard foot, which has a very high surface hardness and excellent scratch resistance. Something like this is being developed.
しかしながら、柔軟性を持つものに関しては、硬化性、
耐摩耗性、耐溶剤性ならびに耐汚染性を併せ有すること
が困難とされていた。However, for those with flexibility, hardening,
It has been difficult to combine wear resistance, solvent resistance, and stain resistance.
一般に、活性エネルギー線硬化型樹脂の硬化性、硬度な
らびに柔軟性などは、活性エネルギー線によって直接、
間接的に反応する官能基の、系内に生成する架橋点の濃
度と分子骨格構造とが大きく影響する。 こういった
観点から、分子中に、架橋点を形成する官能基を多く持
たせるとか、あるいは分子構造を硬いものにすることは
、硬化性や硬度を高くする結果となり、ひいては、耐溶
剤性や耐汚染性も良好なものとなる。In general, the curability, hardness, and flexibility of active energy ray-curable resins are directly affected by active energy rays.
The concentration of crosslinking points generated within the system and the molecular skeleton structure of indirectly reactive functional groups have a large influence. From this point of view, providing a molecule with many functional groups that form crosslinking points or making the molecular structure harder will result in higher curability and hardness, which in turn will improve solvent resistance and The stain resistance is also good.
ところが、このように塗膜の性質を硬いものに設計する
ことにより、柔軟性、屈曲性および伸度などは失われ、
加工が必要なものとか、フレキシブルな基材に対しては
、使用が不向きであった。However, by designing the coating film to be hard, flexibility, flexibility, and elongation are lost.
It was unsuitable for use with things that require processing or flexible base materials.
また、架橋密度を低くしたり、分子骨格構造を柔らかい
ものにすると、屈曲性や伸度などは得られるが、その代
わりに、硬化性、耐溶剤性、耐汚染性、耐摩耗性ならび
に耐擦傷性などが失われてしまい、実用上において、多
大な制限があった。In addition, lowering the crosslinking density or making the molecular skeleton structure softer provides flexibility and elongation, but at the cost of improving hardenability, solvent resistance, stain resistance, abrasion resistance, and scratch resistance. This resulted in a loss of functionality, and there were significant limitations in practical use.
このように、上述した如き従来の技術に従う限りにおい
ては、柔軟性や屈曲性を保持しながら、なおかつ、耐汚
染性や耐薬品性をも確保するということは、まさに、至
難の技であった。In this way, as long as the conventional technology as described above is followed, it has been extremely difficult to maintain flexibility and flexibility while also ensuring stain resistance and chemical resistance. .
そのために、本発明者らは、屈曲性ならびに伸度などの
必要なる用途に対しても勿論、はたまた、硬化性、耐溶
剤性、耐汚染性、耐摩耗性、耐擦傷性ならびに耐候性な
どが要求されるような用途に対しても、それぞれに適用
し得るような、極めて実用性のある樹脂組成物を求めて
、鋭意、研究を開始した。To this end, the present inventors have not only improved flexibility and elongation, but also hardenability, solvent resistance, stain resistance, abrasion resistance, scratch resistance, and weather resistance. We began intensive research in search of extremely practical resin compositions that could be applied to various applications.
したがって、本発明が解決しようとする課題は、−にか
かって、一方では、柔軟性、屈曲性ないしは伸度を確保
しつつ、もう一方においては、硬化性、耐溶剤性、耐汚
染性、耐摩耗性、耐擦傷性ならびに耐候性などをも確保
して、これらの悉くの性質なり性能を兼備するような、
極めて実用性のある、斬新なる樹脂組成物を提供するこ
とである。Therefore, the problem to be solved by the present invention is to ensure flexibility, flexibility or elongation on the one hand, and hardenability, solvent resistance, stain resistance, and resistance on the other hand. It also ensures abrasion resistance, scratch resistance, weather resistance, etc., and combines all of these properties and performances.
The object of the present invention is to provide a novel resin composition that is extremely practical.
そこで、本発明者らは、前述したような従来技術におけ
る未解決の課題の解決を図り、併せて、上述した如き発
明が解決しようとする課題に照準を合わせて、鋭意、検
討を重ねた結果、目的とする悉くの性質なり性能を兼備
した、極めて有用性の高い樹脂組成物を見い出すに及ん
で、本発明を完成するに到った。Therefore, the inventors of the present invention have endeavored to solve the unresolved problems in the prior art as described above, and as a result of intensive studies aimed at the problems to be solved by the invention as described above. The present invention was completed by discovering an extremely useful resin composition that has all the desired properties and performances.
すなわち、本発明は基本的には、必須の有効成分として
、特定のシクロヘキサン環含有ウレタン（メタ）アクリ
レートを含んでなる、電離放射線や光などの活性エネル
ギー線の作用により架橋硬化しうる硬化型樹脂組成物を
提供しようとするものであり、具体的には、必須の有効
成分として、それぞれ、一分子中に少なくとも１個の（
メタ）アクリロイル基および水酸基を併せ有する化合物
（ａ）と、分子内にシクロヘキサン環などの、いわゆる
脂肪族環状構造（脂環式環状構造）を有するポリエステ
ルポリオール（ｂ）と、Ｌ ６−へ牛サンジイソシア
ネート（Ｃ）とを反応させて得られる樹脂を含んで成る
、活性エネルギー線硬化型樹脂組成物を提供しようとす
るものである。That is, the present invention basically relates to a curable resin that can be crosslinked and cured by the action of active energy rays such as ionizing radiation and light, which contains a specific cyclohexane ring-containing urethane (meth)acrylate as an essential active ingredient. Specifically, it is intended to provide a composition containing at least one (
A compound (a) having both a meth)acryloyl group and a hydroxyl group, a polyester polyol (b) having a so-called aliphatic cyclic structure (alicyclic cyclic structure) such as a cyclohexane ring in the molecule, and The present invention aims to provide an active energy ray-curable resin composition comprising a resin obtained by reacting with diisocyanate (C).
ここにおいて、本発明の樹脂組成物の必須の有効成分た
る上記したウレタン（メタ）アクリレー−トとは、その
必須構成物質として、それぞれ、ａ）一分子中に少なく
ても１個の（メタ）アクリロイル基と水酸基とを併せ有
する化合物と、ｂ）分子内に脂肪族環状構造を有するポ
リエステルポリオールと、ｃ）１．５へキサメチレンジ
イソシアネートとを反応させて得られる樹脂を指称する
ものである。Here, the above-mentioned urethane (meth)acrylate, which is an essential active ingredient of the resin composition of the present invention, has as its essential constituents: a) at least one (meth)acrylate in one molecule; It refers to a resin obtained by reacting a compound having both an acryloyl group and a hydroxyl group, b) a polyester polyol having an aliphatic cyclic structure in the molecule, and c) 1.5 hexamethylene diisocyanate.
当該ウレタン（メタ）アクリレートの必須構成質として
用いられる前記した一分子中に少なくても１個の（メタ
）アクリロイル基と水酸基とを併せ有する化合物として
は、公知慣用のものが使用でき、それらのうちでも特に
代表的なものとしては、２−ヒドロキシエチル（メタ）
アクリレート、２−ヒドロ手ジプロピル（メタ）アクリ
レート、２−ヒドロキシブチル（メタ）アクリレ一ト、
３−ヒドロキシブチル（メタ）アクリレート、４−ヒド
ロキシブチル（メタ）アクリレート、ボッエチレングリ
フールモノ（メタ）アクリレート、ポリプロピレングリ
コールモノ（メタ）アクリレート、ペンタエリスリトー
ルトリ （メタ）アクリレト、またはグリシジルメタク
リレート−（メタ）アクリル酸付加物などである。As the compound having at least one (meth)acryloyl group and hydroxyl group in one molecule, which is used as an essential constituent of the urethane (meth)acrylate, known and commonly used compounds can be used. Among them, the most representative one is 2-hydroxyethyl (meth)
Acrylate, 2-hydrodipropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate,
3-Hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, boethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, pentaerythritol tri(meth)acrylate, or glycidyl methacrylate-(meth)acrylate ) acrylic acid adducts, etc.
次いで、当該アクリレートの必須構成物質として用いら
れる前記した分子内に脂肪族環状構造を有するポリエス
テルポリオール（ｂ）としては、公知慣用の素原料から
脱水縮合反応やエステル交換反応などの手段によって合
成されたものが使用できるが、原料であるポリオールま
たは酸成分は、それらのいずれか、あるいは、それらの
両方が、脂肪族環状構造を一部あるいはすべて有してい
ることが必要である。 好ましくは、この脂肪族環状構
造がシクロヘキサン環であることが適切であり、また、
そのシクロヘキサン環が、酸成分から導入されたものが
望ましい。Next, the polyester polyol (b) having an aliphatic cyclic structure in the molecule, which is used as an essential constituent of the acrylate, is synthesized from known and commonly used raw materials by means such as dehydration condensation reaction and transesterification reaction. However, it is necessary that either or both of the raw material polyol or acid component have an aliphatic cyclic structure, in part or in its entirety. Preferably, this aliphatic cyclic structure is a cyclohexane ring, and
It is desirable that the cyclohexane ring is introduced from an acid component.
また、このときのアルコール成分としては、鎖状構造を
有したものが有用である。Moreover, as the alcohol component at this time, one having a chain structure is useful.
かかるポリエステルポリオールとして、その代表的な原
料を挙げれば、ポリオール成分としては、エチレングリ
フール、１，３−プロピレングリフール、１． ２−７
’ロビレングリコール、ジエチレンクリコール、ジプロ
ピレングリコール、ネオペンチルグリコール、１，３−
ブタンジオール、ｌ。Typical raw materials for such polyester polyols include ethylene glyfur, 1,3-propylene glyfur, 1. 2-7
'Robylene glycol, diethylene glycol, dipropylene glycol, neopentyl glycol, 1,3-
butanediol, l.
４−ブタンジオール、１，６−へ牛サンジオール、１．
９−ノナンジオール、１．１０−デカンジオール、２．
２． ４−トリメチル−１，３−ベンタンジオール、
３−メチル−１，５−ベンタンジオール、ジクロロネオ
ペンチルグリコール、ジブロモネオペンチルグリコール
、ヒドロキシピバリン酸ネオペンチルグリコールエステ
ル、シクロヘキサンジメチロール、１，４−シクロヘキ
サンジオール、トリメチロールエタン、トリメチロール
プロパン、グリセリン、３−メチルペンタン−１゜３．
５−１１Ｊｔ−ル、ペンタエリスリトール、スヒｏ り
ＩＪフール、トリシクロデカンジメチロール、水添ビス
フェノールＡ５ または「ニューコールＰＭ−８７０
１Ｌ、ＢＡ−Ｅ４、ＢＡ−ＥＰもしくはＢＡ−ＰＧ、Ｊ
［日本乳化剤■製の、ビスフェノールＡのエチレンオ
キサイドカーボネートジオールなどが代表例であるし、
酸成分としては、次に挙げる如き公知慣用の各種カルボ
ン酸またはそれらの酸無水物が使用できるが、それらの
うちでも特に代表的なものとしては、マレイン酸、フマ
ル酸、イタコン酸、シトラコン酸、テトラヒドロフタル
酸、ヘット酸、ノ＼イミ１．り酸、クロレンデイソク酸
、ダイマー酸、アジピン酸、こはく酸、アルケニルこは
く酸、セ／ （チン酸、アゼライン酸、２． ２． ４
−トリメチルアジピン酸、１．４−シクロヘキサンジカ
ルボン酸、テレフタル酸、２−ナトリウムスルホテレフ
タル酸、２〜カリウムスルホテレフタル酸、インフタル
酸、５−ナトリウムスルホイソフタル酸、５−カリウム
スルホイソフタル酸、またはジメチルもＬ ＜ ｉｔ
ジエチルなどのような、５−ナトリウム−スルホイソフ
タル酸ジ低級アルキル類、オルソフタル４−スルホフタ
ル酸、１．１０−デカメチレンジカルボン酸、ムコン酸
、シゆつ酸、マロン酸、クルタン酸、トリメリ・ソト酸
、ヘキサヒドロフタル酸、テトラブロムフタル酸、メチ
ルシクロヘキセントリカルボン酸もしくはピロメリット
酸、あるいはこれらの酸無水物などが挙げられる。4-butanediol, 1,6-beef sandiol, 1.
9-nonanediol, 1.10-decanediol, 2.
2. 4-trimethyl-1,3-bentanediol,
3-methyl-1,5-bentanediol, dichloroneopentyl glycol, dibromoneopentyl glycol, hydroxypivalic acid neopentyl glycol ester, cyclohexane dimethylol, 1,4-cyclohexane diol, trimethylolethane, trimethylolpropane, glycerin, 3-methylpentane-1゜3.
5-11 Jt-ol, pentaerythritol, Schioli IJ fur, tricyclodecane dimethylol, hydrogenated bisphenol A5 or "Nukol PM-870"
1L, BA-E4, BA-EP or BA-PG, J
[A typical example is ethylene oxide carbonate diol of bisphenol A manufactured by Nippon Nyukazai ■.
As the acid component, various known and commonly used carboxylic acids or their acid anhydrides such as those listed below can be used, but among them, particularly representative ones include maleic acid, fumaric acid, itaconic acid, citraconic acid, Tetrahydrophthalic acid, het acid, no\imi 1. phosphoric acid, chlorene disuccinic acid, dimer acid, adipic acid, succinic acid, alkenyl succinic acid, cic acid, azelaic acid, 2. 2. 4
- Trimethyladipic acid, 1,4-cyclohexanedicarboxylic acid, terephthalic acid, 2-sodium sulfoterephthalic acid, 2-potassium sulfoterephthalic acid, inphthalic acid, 5-sodium sulfoisophthalic acid, 5-potassium sulfoisophthalic acid, or dimethyl L<it
Dilower alkyl 5-sodium-sulfoisophthalates such as diethyl, orthophthalic acid, 4-sulfophthalic acid, 1,10-decamethylene dicarboxylic acid, muconic acid, citric acid, malonic acid, curtanic acid, trimeri-soto Examples include acids, hexahydrophthalic acid, tetrabromophthalic acid, methylcyclohexentricarboxylic acid, pyromellitic acid, and acid anhydrides thereof.
さらには、これらの酸成分の低級アルコールのエステル
化物もなた、前述のポリオール成分とのエステル交換反
応により、目的とするポリエステルポリオールを与える
。Furthermore, lower alcohol esterified products of these acid components are also transesterified with the aforementioned polyol component to yield the desired polyester polyol.
当該ウレタン（メタ）アクリレートのウレタン結合は、
前述したそれぞれ、一分子中に少なくとも１個の（メタ
）アクリロイル基と水酸基とを併せ有する化合物（ａ）
と、分子内に脂肪族環状構造を有るポリエステルポリオ
ール（ｂ）中の水酸基成分と、イソシアネート化合物と
の反応によって得られるものであるが、イソシアネート
化合物として１． ６へキサメチレンジイソシアネー
トが好適である。The urethane bond of the urethane (meth)acrylate is
Each of the above-mentioned compounds (a) has at least one (meth)acryloyl group and hydroxyl group in one molecule.
It is obtained by the reaction of the hydroxyl component in the polyester polyol (b) having an aliphatic cyclic structure in the molecule with an isocyanate compound. 6-hexamethylene diisocyanate is preferred.
また、脂肪族インシアネート化合物をインシアヌレート
化せしめて得られる多官能イソシアネート化合物を併用
することによって、硬化性や硬化塗膜の諸物性などを、
−層、改善することができる。In addition, by using a polyfunctional isocyanate compound obtained by converting an aliphatic incyanate compound into incyanurate, the curability and various physical properties of the cured coating film can be improved.
- layer, can be improved.
かかる脂肪族イソシアネート化合物のインシアヌレート
化物たる多官能イソシアネート化合物としては、ジシク
ロヘキシルメタンジイソシア不一トもしくはインホロン
ジイソシアネートの如き脂環式ジイソシアネート化合物
；ヘキづメチレンジイソシアネートもしくはリジンジイ
ソシアネートの如き脂肪族ジイソシアネート化合物；な
たは水添キシリレンジイソシアネートもしくは水添ジフ
ェニルメタン−４，４′ −ジイソシアネートの如きジ
イソシアネート化合物をイソシアヌレート化せしめて得
られる多量体などが代表的なものであるが、好ましくは
へキサメチレンジイソシアネートのイソシアヌレート化
せしめて得られる多量体などが適切である。Examples of polyfunctional isocyanate compounds which are incyanurates of aliphatic isocyanate compounds include alicyclic diisocyanate compounds such as dicyclohexylmethane diisocyanate or inphorone diisocyanate; aliphatic diisocyanate compounds such as hexylmethylene diisocyanate or lysine diisocyanate. Typical examples are polymers obtained by isocyanurating diisocyanate compounds such as hydrogenated xylylene diisocyanate or hydrogenated diphenylmethane-4,4'-diisocyanate, but preferably hexamethylene diisocyanate. Multimers obtained by isocyanurating are suitable.
また、イソシアネート化合物としてヘキサメチレンジイ
ソシアネート以外にも必要なときは、部に、他の止揚の
如き脂肪族イソシアネート化合物を併用することも可能
である。In addition to hexamethylene diisocyanate as an isocyanate compound, if necessary, other aliphatic isocyanate compounds such as diuretics can also be used in combination.
本発明の活性エネルギー線硬化型樹脂組成物には、さら
に必要に応じて、他の成分を加えることが可能である。Other components can be added to the active energy ray-curable resin composition of the present invention, if necessary.
こうした他の成分として、溶剤、反応性希釈剤、光（重
合）開始剤、ポリマー 重合禁止剤、酸化防止剤、分散
剤、界面活性剤、無機充填剤、無機顔料、または有機顔
料などを加えることができる。These other ingredients may include solvents, reactive diluents, photo(polymerization) initiators, polymerization inhibitors, antioxidants, dispersants, surfactants, inorganic fillers, inorganic pigments, or organic pigments. I can do it.
溶剤としては、トルエンもしくはキシレンの如キ芳香族
炭化水素類：メチルエチルケトン、メチルイソブチルケ
トンもしくはシクロヘキサノンの如きケトン類：酢酸メ
チル、酢酸エチルもしくは酢酸ブチルの如きエステル類
；メタノール、エタノール、プロパツールもしくはブタ
ノールの如きアルコール類、ヘキサン、ヘプタンの如き
脂肪族炭化水素類をはじめ、セロソルブアセテート、カ
ルピトールアセテート、ジメチルホルムアミド、または
テトラヒドロフランなどが挙げられる。Solvents include aromatic hydrocarbons such as toluene or xylene; ketones such as methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; esters such as methyl acetate, ethyl acetate or butyl acetate; methanol, ethanol, propatool or butanol. Examples include alcohols such as hexane, aliphatic hydrocarbons such as heptane, cellosolve acetate, carpitol acetate, dimethylformamide, and tetrahydrofuran.
前記反応性希釈剤としては、単官能性のものから多官能
性のものまでが幅広（用いられるか、それらのうちでも
特に代表的なもののみを例示するに留めれば、２−ヒド
ロキシエチル（メタ）アクリレート、２−ヒドロキシプ
ロピル（メタ）アクリレート、２−エチルヘキシル（メ
タ）アクリレート、Ｎ−ビニルピロリドン、１−ビニル
イミダゾール、インボルニル（メタ）アクリレート、テ
トラヒドロフルフィリル（メタ）アクリレート、カルピ
トール（メタ）アクリレート、フェノキシエチル（メタ
）アクリレート、ジシクロペンタジェン（メタ）アクリ
レート、１，３−ブタンジ（メタ）アクリレート、１，
４−ヘキサンジオールジ（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、ヒドロキシ
ピノでリン酸エステルネオベンチルグリコールジ（メタ
）アクリレート、トリメチロールブロノ寸ントリ （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、ペンタエリスリトールテトラ（メタ）ア
クリレートまたはジペンタエリスリトールヘキサ（メタ
）アクリレートなどである。A wide range of reactive diluents can be used, ranging from monofunctional to polyfunctional ones. Among them, 2-hydroxyethyl ( meth)acrylate, 2-hydroxypropyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, N-vinylpyrrolidone, 1-vinylimidazole, inbornyl(meth)acrylate, tetrahydrofurphyryl(meth)acrylate, carpitol(meth)acrylate Acrylate, phenoxyethyl (meth)acrylate, dicyclopentadiene (meth)acrylate, 1,3-butane di(meth)acrylate, 1,
4-hexanediol di(meth)acrylate, polyethylene glycol di(meth)acrylate, hydroxypino phosphate ester neobentyl glycol di(meth)acrylate, trimethylolbromine tri(meth)acrylate pentaerythritol tri(meth)acrylate
acrylate, pentaerythritol tetra(meth)acrylate or dipentaerythritol hexa(meth)acrylate.
本発明で言う前記活性エネルギー線とは、電子線、α線
、β線、γ線、Ｘ線、中性子線、または紫外線の如き、
ｉｉｗ性放耐放射線などを総称するものである。The active energy rays referred to in the present invention include electron beams, α rays, β rays, γ rays, X rays, neutron rays, and ultraviolet rays.
It is a general term for iiw radiation resistance, etc.
かかるエネルギー線として紫外線を用いて、本発明の樹
脂組成物を硬化させる場合には、波長が１．０００〜８
，０００ 人（オングストローム）なる紫外線により
解離してラジカルを発生するような光（ｆｉ合）開始剤
を使用すべきであり、かかる光（重合）開始剤としては
公知慣用のものが、いずれも使用できるが、そのうちで
も代表的な例を挙げるに止めれば、アセトフェノン類、
ベンゾフェノン、ミヒラーズケトン、ベンジン、ベンゾ
イン・ベンゾエート、ベンゾイン、ベンツインメチルエ
ーテル類、ベンジル・ジメチルケタール、α−アジロキ
シムエステル、チオキサントン類、アンスラキノン類お
よびそれらの各種誘導体などである。When curing the resin composition of the present invention using ultraviolet rays as such energy rays, the wavelength is 1.000 to 8.
A photo(polymerization) initiator that dissociates to generate radicals when exposed to ultraviolet light of 1,000 angstroms should be used, and any known and commonly used photo(polymerization) initiators can be used. However, some representative examples include acetophenones,
These include benzophenone, Michler's ketone, benzine, benzoin benzoate, benzoin, benzine methyl ethers, benzyl dimethyl ketal, α-aziroxime ester, thioxanthone, anthraquinone, and various derivatives thereof.
また、こうした光（重合）開始剤に公知慣用の光増感剤
をも併用することができるが、かかる光増感剤として特
に代表的なもののみを例示するに留めれば、アミン類、
尿素類、含硫黄化合物、含燐化合物、含塩素化合物、ま
たはニトリル類ないしはその他の含窒素化合物などであ
る。In addition, known and commonly used photosensitizers can also be used in combination with such photo(polymerization) initiators, but only representative examples of such photosensitizers include amines,
These include ureas, sulfur-containing compounds, phosphorus-containing compounds, chlorine-containing compounds, nitrites, and other nitrogen-containing compounds.
前述のポリマーとしては、飽和ないし不飽和のもので硬
化塗膜の物性等の改質あるいはコストの低減を目的とし
て添加することができる。The above-mentioned polymers may be saturated or unsaturated and may be added for the purpose of modifying the physical properties of the cured coating film or reducing costs.
こうしたものの例としては、アクリル樹脂、ポリエステ
ル樹脂、ポリアミド樹脂、エポキシ樹脂、ポリウレタン
樹脂、塩化ビニル−酢酸ビニル共重合樹体、ポリビニル
ブチラール樹脂、繊維素系樹脂または塩素化ポリプロピ
レンなどを挙げることができる。Examples of such resins include acrylic resins, polyester resins, polyamide resins, epoxy resins, polyurethane resins, vinyl chloride-vinyl acetate copolymers, polyvinyl butyral resins, cellulose resins, and chlorinated polypropylene.
前述の無機充填剤として代表的なものには、硫酸バリウ
ム、炭酸カルシウム、タルク、マイカ、クレー、炭酸バ
リウム、石膏、アルミナ白、シリカ、珪酸カルシウム、
炭酸マグネシウム シリカパウダー コロイダルシリカ
、アスベスト粉末、水酸化アルミニウム、ステアリン酸
亜鉛の如き体質顔料などをはじめ、黄鉛、ジンククロメ
ートもしくはモリブデ−１・・オレンジの如きクロム酸
塩、紺青の如きフェロシアン化物、酸化チタン、亜鉛華
、ベンガラ、酸化鉄、炭化クロムグリーンの如き金属酸
化物、カドミウムイエロー カドミウムレッドもしくは
硫化水銀の如き金属硫化物、セレン化物もしくは硫酸鉛
の如き硫酸塩、群青の如き珪酸塩、あるいは炭酸塩、コ
バルト・ノくイオレ・ノドもしくはマンガン紫の如き燐
酸塩、まタハアルミニウム粉、亜鉛末、真鍮粉、マグネ
シウム粉、鉄粉、銅粉もしくはニッケル粉の如き金属粉
、さらにはカーボンブラックなどの無機顔料；そしてア
ゾ顔料、フタロシアニン・ブルー フタロシアニン・グ
リーンの如き銅フタロシアニン系顔料、またはキナクリ
ドン系顔料等の有機顔料などがある。Typical inorganic fillers mentioned above include barium sulfate, calcium carbonate, talc, mica, clay, barium carbonate, gypsum, white alumina, silica, calcium silicate,
Magnesium carbonate, silica powder, colloidal silica, asbestos powder, aluminum hydroxide, extender pigments such as zinc stearate, yellow lead, zinc chromate or molybdenum-1...chromates such as orange, ferrocyanide such as deep blue, Metal oxides such as titanium oxide, zinc white, red iron oxide, iron oxide, chromium carbide green, cadmium yellow, metal sulfides such as cadmium red or mercury sulfide, sulfates such as selenide or lead sulfate, silicates such as ultramarine, or Carbonates, phosphates such as cobalt, oxide, or manganese purple, metal powders such as aluminum powder, zinc powder, brass powder, magnesium powder, iron powder, copper powder or nickel powder, and even carbon black, etc. and organic pigments such as azo pigments, copper phthalocyanine pigments such as phthalocyanine blue and phthalocyanine green, and quinacridone pigments.
かくして得られる本発明の活性エネルギー線硬化型樹脂
組成物は、通常はそのまま、止揚した如き活性エネルギ
ー線を照射させて硬化せしめればよい。The active energy ray-curable resin composition of the present invention thus obtained may normally be cured by irradiation with a suspended active energy ray.
本発明の活性エネルギー線硬化型樹脂組成物は塗料用な
らびに印刷インキ用などとして使用することができる、
極めて有用なものである。The active energy ray-curable resin composition of the present invention can be used for paints, printing inks, etc.
It is extremely useful.
次に、本発明を合成例、実施例および比較例ならびに参
考例により、−層、詳細に説明するが、本発明はこれら
実施例に限定されるものではない０以下において、部お
よび％は特に断りのない限り、すべて重量基準であるも
のとする。Next, the present invention will be explained in detail with reference to Synthesis Examples, Examples, Comparative Examples, and Reference Examples, but the present invention is not limited to these Examples. Unless otherwise specified, all prices are based on weight.
合成例 １（脂肪族環状構造を有するポリエステルポリ
オールの合成例）
温度計、攪拌機およびコンデンサーを備えたフラスコに
、３−メチル−１，５ベンタンジオールの３６０ｇ、１
．４−シクロヘキサンジカルボン酸の３４４ｇを仕込ん
で、常法により縮合して水酸基価が１７８ＫＯＨ−ｍｇ
／ｇなる脂肪族環状構造含有のポリエステルポリオール
（ｂ−１−１）を得た。Synthesis Example 1 (Synthesis example of polyester polyol having an aliphatic cyclic structure) Into a flask equipped with a thermometer, a stirrer, and a condenser, 360 g of 3-methyl-1,5-bentanediol and 1
．． 344 g of 4-cyclohexanedicarboxylic acid was charged and condensed using a conventional method to obtain a hydroxyl value of 178 KOH-mg.
/g of aliphatic cyclic structure-containing polyester polyol (b-1-1) was obtained.
合成例 ２（同上）
温度計、攪拌機およびコンデンサーを備えたフラスコに
、ネオペンチルグリコールを２０８ｇ。Synthesis Example 2 (same as above) 208 g of neopentyl glycol was placed in a flask equipped with a thermometer, stirrer, and condenser.
１．４−ブタンジオール９０ｇおよびシクロヘキサンジ
カルボン酸を３４４ｇ仕込み公知の方法で縮合して水酸
基価１９５ＫＯＨ−ｍｇ／Ｈの脂肪族環状構造を持つポ
リエステルポリオール（ｂ−１−２）を得た。90 g of 1,4-butanediol and 344 g of cyclohexanedicarboxylic acid were charged and condensed by a known method to obtain a polyester polyol (b-1-2) having a hydroxyl value of 195 KOH-mg/H and having an aliphatic cyclic structure.
合成例 ３（同上）
温度計、攪拌機およびコンデンサーを備えたフラスコに
３−メチル−１，５ベンタンジオールを２３６ ｇ、ネ
オペンチルグリコール１１４ｇ へキサヒドロ無水フタ
ル酸を３０４ｇ仕込み公知の方法で縮合して水酸基価１
９３ＫＯＨ−ｍｇ／Ｈの脂肪族環状構造を持つポリエス
テルポリオール（ｂ−１−３）を得た。Synthesis Example 3 (same as above) 236 g of 3-methyl-1,5-bentanediol, 114 g of neopentyl glycol, and 304 g of hexahydrophthalic anhydride were placed in a flask equipped with a thermometer, stirrer, and condenser, and condensed using a known method to form a hydroxyl group. Value 1
A polyester polyol (b-1-3) having an aliphatic cyclic structure of 93 KOH-mg/H was obtained.
合成例 ４（脂肪族環状構造を持たない対照用ポリエス
テルポリオールの合成例）
温度計、攪拌機およびコンデンサーを備えたフラスコに
１，４−ブタンジオール３８０ｇおよびアジピン酸を４
３８ｇ仕込み公知の方法で縮合して、水酸基価が１９０
ＫＯＨ−ｍｇ／ｇなる対照用のポリエステルポリオール
（ｂ“−１−１）を得た。Synthesis Example 4 (Synthesis example of control polyester polyol without aliphatic cyclic structure) 380 g of 1,4-butanediol and 4 ml of adipic acid were placed in a flask equipped with a thermometer, a stirrer, and a condenser.
38g was prepared and condensed using a known method, resulting in a hydroxyl value of 190.
A control polyester polyol (b"-1-1) of KOH-mg/g was obtained.
参考例 １ 〔脂環式環状構造含有ウレタン（メタ）ア
クリレートの調製例〕
温度計、攪拌機およびコンデンサーを備えたフラスコに
、ヘキサメチレンジイソシアネート５０゜４ｇと、「バ
ー７ツクＤＮ−９０１ＳＪ Ｃ大８本インキ化学工業
（株）製の、イソシアヌレート化せしめたヘキサメチレ
ンジイソシアネート〕の５４．７ｇと、メチルエチルケ
トンの３３３ｇを仕込んで均一に攪拌したのち、合成例
１で得られたポリエステルポリオール（ｂ−１−１）
の１８９ｇを加えて８０℃で２時間反応を行なった。Reference Example 1 [Preparation example of urethane (meth)acrylate containing an alicyclic ring structure] In a flask equipped with a thermometer, a stirrer, and a condenser, 50° 4 g of hexamethylene diisocyanate and 8 large bottles of DN-901SJ C were placed in a flask equipped with a thermometer, stirrer, and condenser. After charging 54.7 g of isocyanurated hexamethylene diisocyanate (manufactured by Ink Kagaku Kogyo Co., Ltd.) and 333 g of methyl ethyl ketone and stirring uniformly, the polyester polyol obtained in Synthesis Example 1 (b-1- 1)
189g of was added thereto and the reaction was carried out at 80°C for 2 hours.
次いで、２−ヒドロキシプロピルアクリレートの４０ｇ
を添加して、さらに２時間同温度にて反応を続行させた
。Then 40g of 2-hydroxypropyl acrylate
was added thereto, and the reaction was continued at the same temperature for an additional 2 hours.
を考例 ２（同上）
温度計、攪拌機およびコンデンサーを備えたフラスコに
ヘキサメチレンジイソシアネートの５０゜４ｇ１ ［バ
ーノックＤＮ−９０１ＳＪの５４．７ｇおよびメチルエ
チルケトンの３００ｇを仕込んで均一に攪拌したのち、
合成例２で得で得られたポリエステルポリオール（ｂ−
１−２）の１７２ｇを加えて８０°Ｃで２時間反応を行
なった。Example 2 (same as above) After charging 50° 4 g of hexamethylene diisocyanate [54.7 g of Burnock DN-901SJ and 300 g of methyl ethyl ketone] into a flask equipped with a thermometer, stirrer and condenser, and stirring uniformly,
Polyester polyol (b-
1-2) was added and the reaction was carried out at 80°C for 2 hours.
次いで、２−ヒドロ牛ジエチルアクリレートを３４．８
ｇ添加しさらに２時間同温度にて反応を行なった。Then, 2-hydrobovine diethyl acrylate was added to 34.8
g was added, and the reaction was further carried out at the same temperature for 2 hours.
参考例 ３（同上）
温度計、攪拌器及びコンデンサーを備えたフラスコにへ
キサメチレンジイソシアネート５０．４ｇ、「バーノッ
クＤＮ−９０１ＳＪの５４．７ｇおよびメチルエチルケ
トンの３３３ｇを仕込み均一に攪拌した後、合成例 ３
で得られたポリエステルポリオール（ｂ−１−３）の１
７４ｇを加え８０℃で２時間反応を行なった。Reference Example 3 (same as above) 50.4 g of hexamethylene diisocyanate, 54.7 g of Burnock DN-901SJ, and 333 g of methyl ethyl ketone were charged into a flask equipped with a thermometer, stirrer, and condenser, and after stirring uniformly, Synthesis Example 3
1 of the polyester polyol (b-1-3) obtained in
74 g was added and the reaction was carried out at 80°C for 2 hours.
次いで、２−ヒドロキシプロピルアクリレートを４０ｇ
添加しさらに２時間同温度にて反応を行なった。Next, 40g of 2-hydroxypropyl acrylate
After addition, the reaction was continued at the same temperature for an additional 2 hours.
参考例 ４（同上）
温度計、攪拌機およびコンデンサーを備えたフラスコに
ヘキサメチレンジイソシアネートの５０４ｇ１ 「バー
ノックＤＮ−９０１ＳＪの５４．７ｇ１ シクロへキ
シルアクリレート１０４ｇおよび１．６−ヘキサンジオ
ールジアクリレートの１０４ｇを仕込み均一に攪拌した
後、合成例２で得られたポリエステルポリオール（ｂ−
１−２）の１７２ｇを加え８０°Ｃで２時間反応を行な
った。Reference Example 4 (same as above) 504 g of hexamethylene diisocyanate, 54.7 g of Burnock DN-901SJ, 104 g of cyclohexyl acrylate, and 104 g of 1.6-hexanediol diacrylate were charged into a flask equipped with a thermometer, stirrer, and condenser, and uniformly mixed. After stirring, the polyester polyol (b-
172 g of 1-2) was added and the reaction was carried out at 80°C for 2 hours.
次いで、２−ヒドロ牛ジエチルアクリレートを３４．８
ｇ添加しさらに２時間同温度にて反応を行なった。Then, 2-hydrobovine diethyl acrylate was added to 34.8
g was added, and the reaction was further carried out at the same temperature for 2 hours.
参考例 ５（同上）
温度計、攪拌きおよびコンデンサーを備えたフラスコに
ヘキサメチレンジイソシアネートの７０ｇ、シクロへキ
シルアクリレートの９０ｇおよび１．６−へ牛サンジオ
ールジアクリレートの９０ｇを仕込み均一に攪拌した後
、合成例 ２で得たポリエステルポリオール（ｂ−１−
２）の１８９ｇを加え８０℃で２時間反応を行なった。Reference Example 5 (same as above) 70 g of hexamethylene diisocyanate, 90 g of cyclohexyl acrylate, and 90 g of 1.6-beef sane diol diacrylate were charged into a flask equipped with a thermometer, stirrer, and condenser and stirred uniformly. , polyester polyol obtained in Synthesis Example 2 (b-1-
189 g of 2) was added and the reaction was carried out at 80°C for 2 hours.
次ぎに２−ヒドロキシエチルアクリレートを３１ｇ添加
しさらに２時間同温度にて反応を続行させた。Next, 31 g of 2-hydroxyethyl acrylate was added, and the reaction was continued for an additional 2 hours at the same temperature.
参考例 ５ 〔対照用ウレタン（メタ）アクリレートの
調製例〕
温度計、攪拌機およびコンデンサーを備えたフラスコに
４，４′ −ジシクロへ牛シルメタンジイソシアネート
の７９ｇ１ メチルエチルケトンの２２３ｇを仕込み均
一に攪拌した後、合成例４で得たポリエステルポリオー
ル（ｂ’−１−１）の１８ｇを加え８０°Ｃで２時間反
応を行なった。Reference Example 5 [Preparation example of urethane (meth)acrylate for comparison] 79 g of 4,4'-dicyclo-cow silmethane diisocyanate and 223 g of methyl ethyl ketone were charged into a flask equipped with a thermometer, a stirrer, and a condenser, and the mixture was stirred uniformly. 18 g of the polyester polyol (b'-1-1) obtained in Synthesis Example 4 was added and the reaction was carried out at 80°C for 2 hours.
次いで、２−ヒドロキシプロピルアクリレートの２６ｇ
を添加しさらに２時間同温度にて反応を続行させた。Then 26 g of 2-hydroxypropyl acrylate
was added, and the reaction was continued at the same temperature for an additional 2 hours.
参考例 ６ 〔対照用非ウレタン（メタ）アクリレート
系樹脂の調製例〕
トリメチロールプロパントリアクリレートの２００ｇと
１，６ヘキサングリコールジアクリレートの１００ｇを
混合攪拌して均一な樹脂とした。Reference Example 6 [Preparation example of non-urethane (meth)acrylate resin for comparison] 200 g of trimethylolpropane triacrylate and 100 g of 1,6 hexane glycol diacrylate were mixed and stirred to form a uniform resin.
実施例 １〜５ならびに比較例 １および２各参考例で
得られた、それぞれの樹脂について、各樹脂の固形分に
対して３％の「イルガキュア１８４Ｊ（スイス国チバガ
イギー社製の１−ヒドロキシシクロへキシルフェニルケ
トン）を添加し紫外線硬化型塗料を調製した。 これ
らをＰＥＴフィルム上に乾燥膜厚的２０μｍになるよう
にバーコーターにて塗布を行なった。Examples 1 to 5 and Comparative Examples 1 and 2 For each resin obtained in each reference example, 3% of the solid content of each resin was added to Irgacure 184J (manufactured by Ciba Geigy, Switzerland). xylphenylketone) was added to prepare an ultraviolet curable paint.These were coated onto a PET film using a bar coater to a dry film thickness of 20 μm.
次いで、実施例１〜３および比較例１については、予備
乾燥を８０℃で１０分間行なったのちに、一方、実施例
４．５および比較例２については、塗料の塗布後にそれ
ぞれ、８０Ｗの高圧水銀灯で１００ｍｊ／ｃｍ２の紫外
線照射を行なった。Next, Examples 1 to 3 and Comparative Example 1 were pre-dried at 80°C for 10 minutes, while Examples 4.5 and Comparative Example 2 were dried at a high pressure of 80 W after application of the paint. Ultraviolet irradiation was performed at 100 mj/cm2 using a mercury lamp.
しかるのち、かくして得られたそれぞれの塗装板につい
て、摩耗輪Ｃ５−１０Ｆ、５００ｇの荷重で１００回テ
ーパー摩耗試験を行なってヘイズの変化を測定した。Thereafter, a taper abrasion test was conducted on each of the thus obtained coated plates 100 times using an abrasion wheel C5-10F and a load of 500 g to measure changes in haze.
また、油性インク使用フェルトベンにてこれら塗装板上
に線を引いて１時間後にメタノールで拭き取ったのちの
残留汚染の程度（耐汚染性）を見た。In addition, lines were drawn on these coated plates using a felt marker using oil-based ink, and after 1 hour they were wiped off with methanol to check the degree of residual stain (stain resistance).
さらに、塗膜単体の５０％伸張試験を行なって塗膜の外
観を観察した。Furthermore, a 50% elongation test was conducted on the coating film alone, and the appearance of the coating film was observed.
それぞれの結果を、まとめて、第１表にに示す。The results are summarized in Table 1.
実施例 ６〜１０ならびに比較例 ３および４各参考例
で得られた、それぞれの樹脂について、下記する如き配
合にて着色塗料を調製した。Examples 6 to 10 and Comparative Examples 3 and 4 Colored paints were prepared using the resins obtained in each of the reference examples in the following formulations.
参考例で得られた各樹脂の固形分 ５０「タイベーク
ＣＲ−９０Ｊ ＊ ５０トル工ン＊本
適量本石原産業（株）製の
ルチル型酸化チタン孝＊アプリケ−ジョンソリッド４０
％まで希釈以上配合にて高速分散機にて１１０００ＲＰ
にて１時間塗料化を行なった。Solid content of each resin obtained in reference example 50 "Tie Bake CR-90J * 50 Torr * book
Appropriate amount Rutile type titanium oxide *Application Solid 40 manufactured by Ishihara Sangyo Co., Ltd.
11000RP with a high speed dispersion machine when diluted to % or more
Painting was carried out for 1 hour.
次いで、それぞれの塗料を燐酸亜鉛処理電気亜鉛メツキ
鋼板上にＮＯ，６０のバーコーターにて塗装を行ない、
予備乾燥を８ｏ″Ｃで１０分間行なってから、１７０Ｋ
Ｖの加速電圧にて酸素濃度が１５０ｐｐｍなる窒素雰囲
気下で１０Ｍｒａｄの電子線照射を行なった。Next, each paint was applied onto a zinc phosphate treated electrogalvanized steel plate using a NO.60 bar coater.
Pre-dry at 8o"C for 10 minutes, then dry at 170K.
Electron beam irradiation was performed at an acceleration voltage of 10 Mrad in a nitrogen atmosphere with an oxygen concentration of 150 ppm.
得られた硬化塗装板についてＯＴ、２Ｔのハゼ折り試験
を行なうとともに、油性インク使用フェルトペンにてこ
れら塗装板上に線を引いて１時間後にメタノールで拭き
取ったのちの残留汚染の程度を見るようにして耐汚染性
の試験をも行なった。The obtained cured painted boards were subjected to OT and 2T cross-folding tests, and lines were drawn on these painted boards with a felt-tip pen using oil-based ink, and after 1 hour, they were wiped off with methanol to check the degree of residual contamination. A stain resistance test was also conducted.
それぞれの結果を第２表に示す。The respective results are shown in Table 2.
第
表
実施例
テーパー摩耗 耐汚染性
ΔＨ
伸張試験
実施例
Ｔ
Ｔ
耐汚染性
良好
良好
良好
良好
良好
変化なし
変化なし
変化なし
変化なし
変化なし
合格
合格
合格
合格
合格
合格
合格
合格
合格
合格
良好
良好
良好
良好
良好
比較例
比較例
５゜
９゜
不良
良好
変化なし
膜切れ
不合格
不合格
合格
不合格
不良
良好
〔発明の効果〕
以上のように、本発明の活性エネルギー線硬化型樹脂組
成物は、硬化性に優れるものであることは、もとより、
柔軟性、屈曲性、伸度、耐摩耗性、耐汚染性ならびに耐
擦傷性などに優れるものであることが知れよう。Table Examples Taper wear Stain resistance ΔH Stretch test example T T Stain resistance Good Good Good Good Good Good No change No change No change No change No change Pass Pass Pass Pass Pass Pass Pass Pass Pass Good Good Good Good Comparison Example Comparative Example 5゜9゜Poor Good No change Film breakage Fail Fail Pass Fail Fail Good [Effects of the Invention] As described above, the active energy ray-curable resin composition of the present invention has excellent curability. Of course,
It is known that it has excellent flexibility, flexibility, elongation, abrasion resistance, stain resistance, and scratch resistance.
したがって、本発明の樹脂組成物は、柔軟性、屈曲性な
らびに伸度などの必要なる用途に対しても勿論、はたま
た、硬化性、耐溶剤性、耐汚染性、耐摩耗性、耐擦傷性
ならびに耐候性などが要求されるような用途に対しても
、それぞれに適用し得るような、極めて実用性のあるも
のである。Therefore, the resin composition of the present invention can be used not only for purposes requiring flexibility, flexibility, and elongation, but also for curability, solvent resistance, stain resistance, abrasion resistance, and scratch resistance. It is extremely practical and can be applied to applications that require properties such as durability and weather resistance.
Claims (1)
個の（メタ）アクリロイル基と水酸基とを併せ有する化
合物と、ｂ）分子内に脂肪族環状構造を有するポリエス
テルポリオールと、ｃ）１，６−ヘキサメチレンジイソ
シアネートを反応させて得られる樹脂を含有することを
特徴とする、活性エネルギー線硬化型樹脂組成物。 ２、必須の有効成分として、ａ）一分子中に少なくとも
１個の（メタ）アクリロイル基と水酸基をもつ化合物と
、ｂ）分子内に脂肪族環状構造を有するポリエステルポ
リオールと、ｃ）１，６−ヘキサメチレンジイソシアネ
ートと、ｄ）脂肪族イソシアネート化合物をイソシアヌ
レート化せしめた多官能イソシアネート化合物とを反応
させて得られる樹脂を含有することを特徴とする、活性
エネルギー線硬化型樹脂組成物。 ３、前記した分子内に脂肪族環状構造を有するポリエス
テルポリオールの脂肪族環状構造がシクロヘキサン環で
ある、請求項１または２に記載の活性エネルギー線硬化
型樹脂組成物。 ４、前記した分子内に脂肪族環状構造を有するポリエス
テルポリオールが、酸成分としてシクロヘキサン環構造
を有する化合物を用い、該酸成分とポリオール成分とか
ら得られるものである、請求項１または２に記載の活性
エネルギー線硬化型樹脂組成物。 ５、前記した分子内に脂肪族環状構造を有するポリエス
テルポリオールが、酸成分としてシクロヘキサン環構造
を有する化合物を用い、一方、アルコール成分として脂
肪族ポリオールを用いて得られるものである、請求項１
または２に記載の活性エネルギー線硬化型樹脂組成物。[Claims] 1. As an essential active ingredient, a) at least 1 in one molecule;
Contains a resin obtained by reacting a compound having both (meth)acryloyl groups and hydroxyl groups, b) a polyester polyol having an aliphatic cyclic structure in the molecule, and c) 1,6-hexamethylene diisocyanate. An active energy ray-curable resin composition characterized by: 2. As essential active ingredients, a) a compound having at least one (meth)acryloyl group and a hydroxyl group in one molecule, b) a polyester polyol having an aliphatic cyclic structure in the molecule, and c) 1,6 - An active energy ray-curable resin composition comprising a resin obtained by reacting hexamethylene diisocyanate and d) a polyfunctional isocyanate compound obtained by isocyanurating an aliphatic isocyanate compound. 3. The active energy ray-curable resin composition according to claim 1 or 2, wherein the aliphatic cyclic structure of the polyester polyol having an aliphatic cyclic structure in the molecule is a cyclohexane ring. 4. According to claim 1 or 2, the polyester polyol having an aliphatic cyclic structure in the molecule is obtained from the acid component and the polyol component using a compound having a cyclohexane ring structure as the acid component. Active energy ray curable resin composition. 5. Claim 1, wherein the polyester polyol having an aliphatic cyclic structure in the molecule is obtained by using a compound having a cyclohexane ring structure as the acid component and using an aliphatic polyol as the alcohol component.
or the active energy ray-curable resin composition according to 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2135775A JPH0431422A (en) | 1990-05-25 | 1990-05-25 | Actinic radiation curable resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2135775A JPH0431422A (en) | 1990-05-25 | 1990-05-25 | Actinic radiation curable resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0431422A true JPH0431422A (en) | 1992-02-03 |
Family
ID=15159568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2135775A Pending JPH0431422A (en) | 1990-05-25 | 1990-05-25 | Actinic radiation curable resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0431422A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04311714A (en) * | 1991-04-09 | 1992-11-04 | Nippon Paint Co Ltd | Photocurable resin composition |
| JP2001348516A (en) * | 2000-06-09 | 2001-12-18 | Dainippon Ink & Chem Inc | Resin composition for active energy ray curing type ink |
| JP2005097373A (en) * | 2003-09-22 | 2005-04-14 | Dai Ichi Kogyo Seiyaku Co Ltd | Energy ray-curable resin composition and coating material using the same |
| JP2011213789A (en) * | 2010-03-31 | 2011-10-27 | Dic Corp | Radically polymerizable curable composition, adhesive and laminate obtained by using the same |
| CN102408823A (en) * | 2010-09-21 | 2012-04-11 | 荒川化学工业株式会社 | Non-water-based for plastic film provided with active energy line curing film and plastic film provided with active energy line curing film |
| JP2014525963A (en) * | 2011-07-28 | 2014-10-02 | イーストマン ケミカル カンパニー | Coating for the inner surface of plastic bottles for protection against degradation by volatile organic compounds |
| JP2015048431A (en) * | 2013-09-03 | 2015-03-16 | Dic株式会社 | Photocurable resin composition |
| CN108084391A (en) * | 2016-11-21 | 2018-05-29 | 航天特种材料及工艺技术研究所 | A kind of polyurethane and preparation method thereof |
-
1990
- 1990-05-25 JP JP2135775A patent/JPH0431422A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04311714A (en) * | 1991-04-09 | 1992-11-04 | Nippon Paint Co Ltd | Photocurable resin composition |
| JP2001348516A (en) * | 2000-06-09 | 2001-12-18 | Dainippon Ink & Chem Inc | Resin composition for active energy ray curing type ink |
| JP2005097373A (en) * | 2003-09-22 | 2005-04-14 | Dai Ichi Kogyo Seiyaku Co Ltd | Energy ray-curable resin composition and coating material using the same |
| JP2011213789A (en) * | 2010-03-31 | 2011-10-27 | Dic Corp | Radically polymerizable curable composition, adhesive and laminate obtained by using the same |
| CN102408823A (en) * | 2010-09-21 | 2012-04-11 | 荒川化学工业株式会社 | Non-water-based for plastic film provided with active energy line curing film and plastic film provided with active energy line curing film |
| JP2014525963A (en) * | 2011-07-28 | 2014-10-02 | イーストマン ケミカル カンパニー | Coating for the inner surface of plastic bottles for protection against degradation by volatile organic compounds |
| JP2015048431A (en) * | 2013-09-03 | 2015-03-16 | Dic株式会社 | Photocurable resin composition |
| CN108084391A (en) * | 2016-11-21 | 2018-05-29 | 航天特种材料及工艺技术研究所 | A kind of polyurethane and preparation method thereof |
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