JPH0471404B2 - - Google Patents
Info
- Publication number
- JPH0471404B2 JPH0471404B2 JP60240661A JP24066185A JPH0471404B2 JP H0471404 B2 JPH0471404 B2 JP H0471404B2 JP 60240661 A JP60240661 A JP 60240661A JP 24066185 A JP24066185 A JP 24066185A JP H0471404 B2 JPH0471404 B2 JP H0471404B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylate
- parts
- resin composition
- radiation
- 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.)
- Expired - Lifetime
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 60
- 239000011342 resin composition Substances 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- -1 tetrahydrofurfuryl Chemical group 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 238000001723 curing Methods 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 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 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-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
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- AVFBYUADVDVJQL-UHFFFAOYSA-N phosphoric acid;trioxotungsten;hydrate Chemical compound O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O AVFBYUADVDVJQL-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 229920006305 unsaturated polyester Polymers 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- NLILVWPVOORXHM-UHFFFAOYSA-N (1-hydroxycyclohexyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(O)CCCCC1 NLILVWPVOORXHM-UHFFFAOYSA-N 0.000 description 1
- FHGVOHPTNJPHNI-UHFFFAOYSA-N (1-hydroxycyclohexyl) prop-2-enoate Chemical compound C=CC(=O)OC1(O)CCCCC1 FHGVOHPTNJPHNI-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- CRSWJOWOXRBLSG-UHFFFAOYSA-N 1-(2-butylphenyl)-2,2,2-trichloroethanone Chemical compound CCCCC1=CC=CC=C1C(=O)C(Cl)(Cl)Cl CRSWJOWOXRBLSG-UHFFFAOYSA-N 0.000 description 1
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical compound ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 1
- RWXMAAYKJDQVTF-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl prop-2-enoate Chemical compound OCCOCCOC(=O)C=C RWXMAAYKJDQVTF-UHFFFAOYSA-N 0.000 description 1
- ZKLMKZINKNMVKA-UHFFFAOYSA-N 2-(2-hydroxypropoxy)propan-1-ol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(O)COC(C)CO ZKLMKZINKNMVKA-UHFFFAOYSA-N 0.000 description 1
- YATYDCQGPUOZGZ-UHFFFAOYSA-N 2-(2-hydroxypropoxy)propan-1-ol;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(O)COC(C)CO YATYDCQGPUOZGZ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- KJOFMRLNOMBWIM-UHFFFAOYSA-N 2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C(=O)C1=CC=C(C(C)C)C=C1 KJOFMRLNOMBWIM-UHFFFAOYSA-N 0.000 description 1
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- XFOFBPRPOAWWPA-UHFFFAOYSA-N 6-hydroxyhexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCO XFOFBPRPOAWWPA-UHFFFAOYSA-N 0.000 description 1
- OCIFJWVZZUDMRL-UHFFFAOYSA-N 6-hydroxyhexyl prop-2-enoate Chemical compound OCCCCCCOC(=O)C=C OCIFJWVZZUDMRL-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- YKODZEIHQDLCLN-UHFFFAOYSA-N C1=CC=CC=2SC3=CC=CC=C3C(C12)=O.C(C)(C)C1=CC=2C(C3=CC=CC=C3SC2C=C1)=O Chemical compound C1=CC=CC=2SC3=CC=CC=C3C(C12)=O.C(C)(C)C1=CC=2C(C3=CC=CC=C3SC2C=C1)=O YKODZEIHQDLCLN-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- PIVJNJNFYIELGJ-UHFFFAOYSA-I O.[Mg++].[Al+3].OOC([O-])=O.OOC([O-])=O.OOC([O-])=O.OOC([O-])=O.OOC([O-])=O Chemical compound O.[Mg++].[Al+3].OOC([O-])=O.OOC([O-])=O.OOC([O-])=O.OOC([O-])=O.OOC([O-])=O PIVJNJNFYIELGJ-UHFFFAOYSA-I 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 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
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- NBICYCZLCAMSBG-UHFFFAOYSA-L [Co+2].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O Chemical compound [Co+2].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O NBICYCZLCAMSBG-UHFFFAOYSA-L 0.000 description 1
- COYJIMCVCRLOIW-UHFFFAOYSA-L [Mn+2].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O Chemical compound [Mn+2].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O COYJIMCVCRLOIW-UHFFFAOYSA-L 0.000 description 1
- UEZFOZPTSDJYNK-UHFFFAOYSA-I [V+5].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O Chemical compound [V+5].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O UEZFOZPTSDJYNK-UHFFFAOYSA-I 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 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
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000001227 electron beam curing Methods 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 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
- 238000013007 heat curing Methods 0.000 description 1
- AYSGVHDKKKNZRR-UHFFFAOYSA-L iron(2+) oct-2-enoate Chemical compound [Fe+2].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O AYSGVHDKKKNZRR-UHFFFAOYSA-L 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- BCTWNMTZAXVEJL-UHFFFAOYSA-N phosphane;tungsten;tetracontahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W] BCTWNMTZAXVEJL-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tertâbutyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229910000349 titanium oxysulfate Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
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[Industrial Application Field] The present invention relates to a radiation-curable resin composition, and more specifically, it has excellent curing properties and physical properties of the cured product,
The present invention relates to a novel radiation-curable resin composition useful for various uses such as inks, paints, and adhesives. [Prior art] Resins that are cured by radiation such as ultraviolet rays or electron beams have advantages over thermosetting resins that are cured by heat, such as resource saving, non-pollution, and rapid curing, so they are widely used. It's being used. In general, radiation-curable resin compositions are made by using a prepolymer such as polyester (meth)acrylate, urethane (meth)acrylate, epoxy (meth)acrylate, or polyether (meth)acrylate or unsaturated polyester as a resin component, and using tetrahydrofuranate as a resin component. Mono(meth)acrylates such as furyl(meth)acrylate and phenoxyethyl(meth)acrylate, and polyol poly(meth)acrylates such as 1,6-hexanediol di(meth)acrylate and trimethylolpropane tri(meth)acrylate. It is made by blending reactive diluent components such as. Until now, by changing the blending ratio of these components, radiation-curable resin compositions suitable for each use have been obtained. [Problems to be solved by the invention] However, it is difficult to obtain a resin composition that is well-balanced in terms of curing speed and physical properties of the cured product simply by blending conventionally known components. Therefore, there is a demand for the development of a new radiation-curable resin composition that is well-balanced in both curing speed and physical properties of the cured product. The present inventors conducted various studies in view of the above circumstances, and as a result, arrived at the present invention. Therefore, the present invention provides a radiation-curable resin composition that can be used for various purposes. [Means and effects for solving the problems] The present invention is based on the general formula [] (However, in the formula, R is a hydrogen atom or a methyl group, which may be the same or different, and Z is a divalent aliphatic hydrocarbon group having 2 to 6 carbon atoms, and (n is an integer from 1 to 100) as an essential component. The present invention relates to a radiation-curable resin composition. The hydroxyl group-containing (meth)acrylate oligomer represented by the general formula [] used in the present invention has the general formula [] (In the formula, R is a hydrogen atom or a methyl group, Z
is a divalent aliphatic hydrocarbon group having 2 to 6 carbon atoms and may have an ether bond in the molecule. ) It is obtained by addition polymerizing and oligomerizing a hydroxyl group-containing (meth)acrylate represented by: Specific examples of the hydroxyl group-containing (meth)acrylate represented by the general formula [] include hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate,
Hydroxybutyl methacrylate, hydroxyhexyl acrylate, hydroxyhexyl methacrylate, diethylene glycol monoacrylate, diethylene glycol monomethacrylate,
Examples include dipropylene glycol monoacrylate, dipropylene glycol monomethacrylate, hydroxycyclohexyl acrylate, hydroxycyclohexyl methacrylate, and the like. These may be used alone or as a mixture. To oligomerize a hydroxyl group-containing (meth)acrylate by addition polymerizing it, for example, as described in Japanese Patent Application No. 59-256558, the hydroxyl group-containing (meth)acrylate is treated with a protonic acid such as sulfuric acid or para-toluenesulfonic acid; boron trifluoride,
Maintained at a temperature of 10 to 150°C in the presence of catalysts such as Lewis acids such as tin tetrachloride; oxysulfates such as titanium oxysulfate; heteropolyacids such as tungstophosphoric acid, tungstosilicic acid, molybdophosphoric acid, molybdosilicic acid, etc. do it. The radiation-curable resin composition of the present invention contains a hydroxyl group-containing (meth)acrylate oligomer represented by the above general formula [] as an essential component, and contains a hydroxyl group-containing (meth)acrylate oligomer represented by the above general formula []. ) The radiation-curable resin composition of the present invention can be obtained by using the acrylate oligomer alone or by using the oligomer in combination with a conventional radiation-curable resin composition, a known and commonly used reactive diluent, and various resins. Examples of reactive diluents used as necessary in the present invention include styrene, α-methylstyrene,
Acrylonitrile, (meth)acrylamide, diacetone acrylamide, N-methyl (meth)acrylamide, N-methylol (meth)acrylamide, N-vinylpyrrolidone, diallyl phthalate, allyl glycidyl ether, (meth)acrylic acid, methyl (meth)acrylate Alkyl (meth)acrylates such as, tetrahydrofurfuryl (meth)acrylate, methoxyethyl (meth)acrylate, phenoxyethyl (meth)
Acrylate, dibromopropyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate , polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate
Acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipenta Erythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate,
Trishydroxyethyl isocyanurate tri(meth)acrylate, ethylene oxide added bisphenol A di(meth)acrylate, hydrogenated bisphenol A di(meth)acrylate, dimethylaminoethyl(meth)acrylate, diethylaminoethyl(meth)acrylate, dicyclo Examples include pentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, silicone (meth)acrylate, amide (meth)acrylate, phosphoric acid (meth)acrylate, and the like. These can be used alone or as a mixture. Resins that may be used as necessary in the present invention include:
For example, polyester (meth)acrylate obtained by the reaction of (meth)acrylic acid, glycols, and polybasic acid, epoxy (meth)acrylate obtained by the reaction of (meth)acrylic acid and an epoxy compound, and isocyanate group-containing compounds. Urethane (meth)acrylate obtained by reaction with hydroxyalkyl (meth)acrylate, carboxyl group-containing (meth)acrylate obtained by reaction of carboxylic anhydride and hydroxyalkyl (meth)acrylate
Examples include prepolymers such as acrylates, unsaturated polyesters, epoxy resins, polyamide resins, acrylic resins, polyvinyl alcohols, etc., and these can be used alone or as a mixture. When the above-mentioned reactive diluent or resin is used in the present invention, the amount thereof is not particularly limited, and is appropriately determined depending on the viscosity and curability required of the resulting resin composition or the desired physical properties of the cured product. be able to. The radiation-curable resin composition of the present invention can be applied to or molded onto various substrates by means known to those skilled in the art. Radiation curing can be performed with electron beams, ultraviolet rays, etc. In the case of ultraviolet curing, a normal photopolymerization initiator, and if necessary, a photopolymerization initiator and a sensitizer are used at 0.1
It is incorporated into the composition at a concentration of ~10% by weight. Examples of photopolymerization initiators include benzoin alkyl ethers such as benzoin, benzoin isopropyl ether, and benzoin isobutyl ether;
benzophenone, Michler's ketone, methyl-ο-
Benzophenones such as benzoyl benzoate; acetonephenone, trichloroacetophenone, 2,2-diethoxyacetophenone, p-t
- Acetophenones such as butyltrichloroacetophenone, 2,2-dimethoxy-2-phenylacetophenone, p-dimethylaminoacetophenone; such as xanthone, thioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone Thioxanthone; benzyl, 2-
Ethyl anthraquinone, methyl-benzoylformate, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-
Examples of sensitizers include 4'-isopropyl-2-methylpropiophenone, 1-hydroxycyclohexyl phenyl ketone, tetramethylthiuram monosulfide, and allyldiazonium salts. Examples of sensitizers include amine compounds, sulfur compounds, and phosphorus compounds. Can be mentioned. These may be used alone or in combination. Furthermore, ultraviolet curing and thermosetting, or electron beam curing can also be used together. When heat curing is used together, common radical polymerization initiators such as benzoyl peroxide, methyl ethyl ketone peroxide, lauroyl peroxide, cyclohexanone peroxide, t-butyl hydroperoxide, di-t-butyl peroxide, di- t
- aluminum peroxide, dicumyl peroxide,
t-butyl perbenzoate, azobisisobutyronitrile, etc. can be used, and if necessary, radical polymerization accelerators such as cobalt octenoate, cobalt naphthenate, iron octenoate, manganese octenoate, vanadium octenoate, etc. can be used. Organic metal salts, organic amines such as N,N-dimethylaniline, etc. can be used in combination. [Effects of the Invention] The radiation-curable resin composition of the present invention has excellent curability and adhesion to substrates, and also has excellent physical properties of the cured product such as hardness of the cured product obtained by curing.
Paints, adhesives, inks, hard coats, resists, protective films for printed wiring boards, encapsulants, binders,
It can be used for a wide range of purposes such as insulating varnish and overprint varnish. [Example] Next, the present invention will be explained with reference to Examples, but the present invention is not limited to these Examples.
Note that parts in the examples are parts by weight. Reference Example 1 A reaction vessel equipped with a thermometer and a stirrer was charged with 232 parts of 2-hydroxyethyl acrylate, 0.07 parts of hydroquinone monomethyl ether as a polymerization inhibitor, and 2.3 parts of 12-tungstophosphoric acid as a catalyst, and then heated to 80°C for 7.5 hours. held. After the reaction is complete, add 12 parts of powdered magnesium silicate as an adsorbent and heat at 40°C.
After stirring for 30 minutes, the reaction product was purified by pressure filtration to produce a colorless transparent liquid reaction product (hereinafter referred to as hydroxyl group-containing acrylate oligomer (1)).
228 parts (yield 98.3%) were obtained. IR, NMR, GPC
From the analysis results, it was found that the reaction product was a hydroxyl group-containing acrylate oligomer with an average molecular weight of 401 and the following structure. Reference Example 2 After charging 260 parts of 2-hydroxypropyl acrylate, 0.08 parts of hydroquinone monomethyl ether as a polymerization inhibitor, and 2.6 parts of 12-tungstosilicic acid as a catalyst into the same reaction vessel as in Reference Example 1,
It was kept at 100â for 5 hours. After the reaction is complete, 13 parts of powdered basic magnesium aluminum hydroxy carbonate hydrate, which is an adsorbent, is added, stirred at 60°C for 30 minutes, and purified by pressurization to form a colorless transparent liquid. product (hereinafter referred to as
It is called hydroxyl group-containing acrylate oligomer (2). ) 251 parts (yield 96.5%) were obtained. The reaction product was a hydroxyl group-containing acrylate oligomer with an average molecular weight of 510 and the following structure. Reference Example 3 Into a reaction vessel similar to Reference Example 1, 260 parts of 2-hydroxyethyl methacrylate, 0.13 parts of hydroquinone monomethyl ether as a polymerization inhibitor, and 2.6 parts of tungstophosphoric acid as a catalyst were charged.
It was kept at â for 4 hours. After the reaction is complete, add 260 parts of water, stir at room temperature, leave to stand, remove the aqueous layer (upper layer), and keep the resulting residual liquid at 80°C for 30 minutes under a reduced pressure of 3 mmHg to remove water and residual liquid. As a result of removing a portion of the raw materials, 102 parts (yield: 39.2%) of a colorless transparent liquid reaction product (hereinafter referred to as hydroxyl group-containing methacrylate oligomer (3)) was obtained. The reaction product was a hydroxyl group-containing methacrylate oligomer with an average molecular weight of 297 and the following structure. Examples 1 to 6 100 parts of a mixture of the hydroxyl group-containing (meth)acrylate oligomers (1) to (3) obtained in Reference Examples 1 to 3 and the prepolymers and/or reactive diluents shown in Table 1 , 0.01 part of hydroquinone monomethyl ether and benzyl dimethyl ketal (manufactured by Ciba Geigy, Irgakiure 651) 5
UV curable resin composition (1) of the present invention
(6) was prepared. Each of the obtained resin compositions (1) to (6) was applied to a thickness of 15Ό on a steel plate panel,
When the panel was irradiated using a high-pressure mercury lamp of 80 W/cm from a distance of 10 cm while moving the panel at a conveyor speed of 6 m/min, a tack-free cured coating film was obtained in each case with a single irradiation. The performance of the obtained cured coating film is shown in Table 1. Comparative Example 1 0.01 part of hydroquinone monomethyl ether and 5 parts of benzyl dimethyl ketal (manufactured by Ciba Geigy, Irgakiure 651) were added to 100 parts of the mixture of the prepolymer and reactive diluent shown in Table 1, and a UV-curable type for comparison was prepared. A resin composition (1) was prepared. Using the obtained comparative resin composition (1), the curability of the coating film was examined in the same manner as in Example 1, and it was found that two irradiations were required to obtain a tack-free cured coating film. The performance of the obtained cured coating film is shown in Table 1. Comparative Example 2 CH 2 =CH-COO (-CH 2 -CH 2 -COO) - 30 parts of 1.4 H acrylic acid oligomer, 60 parts of the same prepolymer PA used in Example 1, and the same prepolymer PA used in Example 1. A comparative ultraviolet curable resin composition (2) was prepared by adding 0.01 part of hydroquinone monomethyl ether and 5 parts of benzyl dimethyl ketal (manufactured by Ciba Geigy, Irgakiure 651) to a mixture of 10 parts of the same reactive diluent TMPTA. Using the obtained comparative resin composition (2), the radiation curability of the coating film was investigated in the same manner as in Example 1.
Two irradiations were required to obtain a tack-free cured coating. Furthermore, the obtained cured coating film had poor smoothness, a pencil hardness of H, and an adhesion of 90/100, and the physical properties of the cured product were inferior to those of the cured coating film obtained in Example 1. Example 7 5 parts of benzyl methyl ketal (manufactured by Ciba Geigy, Irgakiure 651) was added to 100 parts of the hydroxyl group-containing (meth)acrylate oligomer (1) obtained in Reference Example 1 to prepare the ultraviolet curable resin composition of the present invention ( 7) was prepared. The obtained resin composition (7) was applied to a thickness of 15 ÎŒm on a steel plate panel, and irradiated with an 80 W/cm high-pressure mercury lamp from a distance of 10 cm while moving the panel at a conveyor speed of 6 m/min. However, a cured coating film was obtained with one irradiation. The performance of the obtained cured coating film was examined in the same manner as in Example 1, and the pencil hardness was 2B and the adhesion was 100/100.
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Claims (1)
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é æåãšããŠå«æããæŸå°ç·ç¡¬ååæš¹èçµæç©ã[Claims] 1. General formula [] (However, in the formula, R is a hydrogen atom or a methyl group, which may be the same or different,
Z is a divalent aliphatic hydrocarbon group having 2 to 6 carbon atoms, and may have an ether bond in the molecule, and may be the same or different, and n
is an integer from 1 to 100. ) A radiation-curable resin composition containing as an essential component a hydroxyl group-containing (meth)acrylate oligomer.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60240661A JPS62101610A (en) | 1985-10-29 | 1985-10-29 | Radiation-curable resin composition |
| US06/805,342 US4691045A (en) | 1984-12-06 | 1985-12-05 | Hydroxyl group-containing (meth)acrylate oligomer, prepolymer therefrom, and method for use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60240661A JPS62101610A (en) | 1985-10-29 | 1985-10-29 | Radiation-curable resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62101610A JPS62101610A (en) | 1987-05-12 |
| JPH0471404B2 true JPH0471404B2 (en) | 1992-11-13 |
Family
ID=17062815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60240661A Granted JPS62101610A (en) | 1984-12-06 | 1985-10-29 | Radiation-curable resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62101610A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2742808B2 (en) * | 1988-07-14 | 1998-04-22 | è€ååææ ªåŒäŒç€Ÿ | Bilirubin adsorbent with antithrombotic properties |
| KR100668951B1 (en) | 2005-11-17 | 2007-01-12 | 죌ìíì¬ í¬ì€ìœ | Auto looping apparatus for wire |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54109916A (en) * | 1978-01-05 | 1979-08-29 | Bayer Ag | Manufacture of acrylic acid oligomer |
-
1985
- 1985-10-29 JP JP60240661A patent/JPS62101610A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54109916A (en) * | 1978-01-05 | 1979-08-29 | Bayer Ag | Manufacture of acrylic acid oligomer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62101610A (en) | 1987-05-12 |
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