TWI794165B - 光硬化性樹脂組成物、墨水及塗料 - Google Patents
光硬化性樹脂組成物、墨水及塗料 Download PDFInfo
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- TWI794165B TWI794165B TW106110229A TW106110229A TWI794165B TW I794165 B TWI794165 B TW I794165B TW 106110229 A TW106110229 A TW 106110229A TW 106110229 A TW106110229 A TW 106110229A TW I794165 B TWI794165 B TW I794165B
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- Prior art keywords
- resin composition
- photocurable resin
- allyl
- ink
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- 239000011342 resin composition Substances 0.000 title claims abstract description 62
- 239000003973 paint Substances 0.000 title claims description 15
- 239000000976 ink Substances 0.000 title description 41
- -1 allyl compound Chemical class 0.000 claims abstract description 56
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 43
- 229920000642 polymer Polymers 0.000 claims abstract description 39
- 239000003349 gelling agent Substances 0.000 claims abstract description 34
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000002966 varnish Substances 0.000 claims description 22
- 239000003999 initiator Substances 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 5
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 238000003860 storage Methods 0.000 description 16
- 230000004043 responsiveness Effects 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000004641 Diallyl-phthalate Substances 0.000 description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000004033 plastic Substances 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000004743 Polypropylene Substances 0.000 description 7
- 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 7
- 125000006841 cyclic skeleton Chemical group 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 229920001155 polypropylene Polymers 0.000 description 7
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 238000004945 emulsification Methods 0.000 description 5
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- 238000002360 preparation method Methods 0.000 description 5
- FPFOSIXCIBGKOH-MTOQALJVSA-J (z)-4-oxopent-2-en-2-olate;zirconium(4+) Chemical compound [Zr+4].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O FPFOSIXCIBGKOH-MTOQALJVSA-J 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920002120 photoresistant polymer Polymers 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- FDUFQLNPPGRIKX-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CC(C)(CO)CO FDUFQLNPPGRIKX-UHFFFAOYSA-N 0.000 description 2
- 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
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 2
- HHCHLHOEAKKCAB-UHFFFAOYSA-N 2-oxaspiro[3.5]nonane-1,3-dione Chemical compound O=C1OC(=O)C11CCCCC1 HHCHLHOEAKKCAB-UHFFFAOYSA-N 0.000 description 2
- HFSHGXIPMHQUFT-UHFFFAOYSA-N 3,8-dihydroxy-2-(hydroxymethyl)-7-methylnon-1-en-4-one Chemical compound CC(O)C(C)CCC(=O)C(O)C(=C)CO HFSHGXIPMHQUFT-UHFFFAOYSA-N 0.000 description 2
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 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
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- MQQXUGFEQSCYIA-OAWHIZORSA-M aluminum;(z)-4-ethoxy-4-oxobut-2-en-2-olate;propan-2-olate Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CCOC(=O)\C=C(\C)[O-] MQQXUGFEQSCYIA-OAWHIZORSA-M 0.000 description 2
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
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- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
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- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 2
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003463 sulfur Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 150000003754 zirconium Chemical class 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- MJEREOGWNZGKRN-UHFFFAOYSA-N 1-(4-aminophenyl)-8-[4-(4-fluorophenyl)-4-oxobutyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=CC(N)=CC=C1N1C2(CCN(CCCC(=O)C=3C=CC(F)=CC=3)CC2)C(=O)NC1 MJEREOGWNZGKRN-UHFFFAOYSA-N 0.000 description 1
- OMOYYCNTSLVTOE-SYXWNFKLSA-N 2-[[(e)-3-(carboxymethylimino)prop-1-enyl]amino]acetic acid Chemical compound OC(=O)CN\C=C\C=NCC(O)=O OMOYYCNTSLVTOE-SYXWNFKLSA-N 0.000 description 1
- AIFLGMNWQFPTAJ-UHFFFAOYSA-J 2-hydroxypropanoate;titanium(4+) Chemical compound [Ti+4].CC(O)C([O-])=O.CC(O)C([O-])=O.CC(O)C([O-])=O.CC(O)C([O-])=O AIFLGMNWQFPTAJ-UHFFFAOYSA-J 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- LNPQMDSMIGLHSR-UHFFFAOYSA-N 2-oxaspiro[3.5]non-5-ene-1,3-dione Chemical compound O=C1OC(=O)C11C=CCCC1 LNPQMDSMIGLHSR-UHFFFAOYSA-N 0.000 description 1
- OKAAOWIRPHWLGF-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)octadecyl propanoate Chemical compound CCCCCCCCCCCCCCCC(CCOC(=O)CC)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 OKAAOWIRPHWLGF-UHFFFAOYSA-N 0.000 description 1
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- SECPSAXXNHPTGS-UHFFFAOYSA-N C(CCC)OC(C(=O)CC(C)=O)(OCCCC)OCCCC.[Zr] Chemical compound C(CCC)OC(C(=O)CC(C)=O)(OCCCC)OCCCC.[Zr] SECPSAXXNHPTGS-UHFFFAOYSA-N 0.000 description 1
- NTHIXHIADTXFMU-UHFFFAOYSA-J C(CO)(=O)[O-].CCCCCCCC.[Ti+4].C(CO)(=O)[O-].C(CO)(=O)[O-].C(CO)(=O)[O-] Chemical compound C(CO)(=O)[O-].CCCCCCCC.[Ti+4].C(CO)(=O)[O-].C(CO)(=O)[O-].C(CO)(=O)[O-] NTHIXHIADTXFMU-UHFFFAOYSA-J 0.000 description 1
- YQEVIZPKEOELNL-UHFFFAOYSA-N CCCCO[Zr] Chemical compound CCCCO[Zr] YQEVIZPKEOELNL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
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- 239000004698 Polyethylene Substances 0.000 description 1
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- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 101000803172 Solanum lycopersicum 1-aminocyclopropane-1-carboxylate synthase 2 Proteins 0.000 description 1
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- 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
- 239000007983 Tris buffer Substances 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
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- WREBYPQOSZWUKP-UHFFFAOYSA-N [4-(5-sulfanylidenedithiol-3-yl)phenyl] 2-propylpentanoate Chemical compound C1=CC(OC(=O)C(CCC)CCC)=CC=C1C1=CC(=S)SS1 WREBYPQOSZWUKP-UHFFFAOYSA-N 0.000 description 1
- GANNOFFDYMSBSZ-UHFFFAOYSA-N [AlH3].[Mg] Chemical class [AlH3].[Mg] GANNOFFDYMSBSZ-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
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- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940009827 aluminum acetate Drugs 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- VEGSIXIYQSUOQG-UHFFFAOYSA-N azane;2-hydroxypropanoic acid;zirconium Chemical compound [NH4+].[Zr].CC(O)C([O-])=O VEGSIXIYQSUOQG-UHFFFAOYSA-N 0.000 description 1
- ZDNFTNPFYCKVTB-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,4-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C=C1 ZDNFTNPFYCKVTB-UHFFFAOYSA-N 0.000 description 1
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- ZXTPJLLIHIDBKQ-UHFFFAOYSA-N bis(prop-2-enyl) cyclohexane-1,4-dicarboxylate Chemical compound C=CCOC(=O)C1CCC(C(=O)OCC=C)CC1 ZXTPJLLIHIDBKQ-UHFFFAOYSA-N 0.000 description 1
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- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
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- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
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Abstract
本發明之目的在於提供一種能夠構成印刷適應性優異之組成物的光硬化性樹脂組成物。
本發明係關於一種光硬化性樹脂組成物，其特徵在於：含有使下述通式(I)表示之烯丙基系化合物進行聚合而獲得之烯丙基系聚合物(A)及膠化劑(B)[通式(I)中，R1及R2分別表示H或CH3，X表示a價基，該a價基為不具有取代基之飽和或一部分不飽和之4~8員環之環狀骨架，a表示2或3]。
Description
本發明係關於一種含有烯丙基系聚合物(A)及膠化劑(B)之光硬化性樹脂組成物，以及含有該樹脂組成物而成之墨水、塗料。更詳細而言，本發明係關於一種印刷適應性優異之光硬化性樹脂組成物。
以往，藉由光(例如紫外線)而硬化之各種樹脂組成物被用於墨水、塗料、接著劑、光阻劑等。例如，紫外線硬化型印刷墨水於以下等方面評價高而實用化不斷擴大：硬化速度快，能夠於短時間內硬化；由於不使用溶劑故而適合環境；低耗節能。
此種樹脂組成物中，含有由酞酸二烯丙酯(鄰酞酸二烯丙酯、間酞酸二烯丙酯、對酞酸二烯丙酯)衍生之酞酸二烯丙酯樹脂之樹脂組成物作為紙用之UV平版印墨(offset ink)被採用。
專利文獻1中，記載有一種活性能量線硬化型印刷墨水用凝膠清漆於印刷機之操作性方面優異，該活性能量線硬化型印刷墨水用凝膠清漆係對含有A.鋁醇化物或鋁螯合化合物、B.酞酸二烯丙酯預聚物及C.與B相溶之活性能量線硬化性液狀化合物之混合物進行加熱而獲得者，但關於印刷適應性仍有改善之餘地。
專利文獻1：日本專利特開2013-091715號公報
本發明之目的在於提供一種能夠構成印刷適應性良好之組成物的光硬化性樹脂組成物。
本發明人經過潛心研究，結果發現含有使具有特定結構之烯丙基系化合物進行聚合而獲得之烯丙基系聚合物(A)及膠化劑(B)的光硬化性樹脂組成物能夠構成印刷適應性(流動性、印刷響應性)良好之組成物，從而思及本發明。
即，本發明之光硬化性樹脂組成物之特徵在於：含有使下述通式(I)表示之烯丙基系化合物進行聚合而獲得之烯丙基系聚合物(A)及膠化劑(B)。
[R1及R2分別表示H或CH3，X表示a價基，該a價基為不具有取代基之飽和或一部分不飽和之4~8員環之環狀骨架，a表示2或3]
若含有使上述通式(I)表示之烯丙基系化合物進行聚合而
獲得之烯丙基系聚合物(A)及膠化劑(B)，則會成為印刷適應性優異之光硬化性樹脂組成物。
本發明之光硬化性樹脂組成物較佳為上述通式(I)中之X具有下述任一環狀骨架。
本發明之光硬化性樹脂組成物較佳進而含有乙烯性不飽和化合物(C)。
藉由含有乙烯性不飽和化合物(C)，可提高光硬化性樹脂組成物之乾燥性及所獲得的硬化物之皮膜強度，又，可調整至適合用於印刷之黏度，
獲得塗佈作業性優異之組成物。
本發明之光硬化性樹脂組成物較佳進而含有光聚合起始劑。藉由含有光聚合起始劑，由光照射引起之聚合順利進行，故而能夠於短時間內獲得更高分子量之聚合物。
本發明之墨水之特徵在於：含有本發明之光硬化性樹脂組成物。該墨水之印刷適應性優異。
本發明之塗料之特徵在於：含有本發明之光硬化性樹脂組成物。又，本發明之塗料較佳為罩光漆。
根據本發明，可獲得於作為墨水、塗料、接著劑及光阻劑之成分使用的情形時，印刷適應性(流動性、印刷響應性)優異之光硬化性樹脂組成物。
本發明之光硬化性樹脂組成物含有使具有特定結構的烯丙基系化合物進行聚合而獲得之烯丙基系聚合物(A)及膠化劑(B)，故而能夠降低於低頻區域(0.01~0.1Hz附近)之儲存彈性模數，具有良好之流動性，及/或能夠增大於高頻區域(10~100Hz附近)之儲存彈性模數，提高高速印刷中之響應速度，獲得良好之印刷響應性。
如此，本發明中藉由併用烯丙基系聚合物(A)及膠化劑(B)，能夠獲得良好之流動性及/或印刷響應性，印刷適應性優異，可較佳地用作墨水、塗料。
又，一般而言，流動性與印刷響應性為二律背反性能，但藉由併用烯丙基系聚合物(A)及膠化劑(B)，進而使用鋁錯合物作為膠化劑(B)，能夠兼顧流動性與印刷響應性，印刷適應性更優異，可更佳地用作墨水、塗料。
再者，令人震驚之見解是藉由併用烯丙基系聚合物(A)、膠化劑(B)，能夠降低於低頻區域(0.01~0.1Hz附近)之儲存彈性模數。
推測藉由在含有烯丙基系聚合物(A)之同時含有膠化劑(B)，疑似地形成交聯鏈，於高頻區域之儲存彈性模數增大，響應速度變快，獲得良好之印刷響應性。另一方面，能夠降低於低頻區域之儲存彈性模數的理由雖不明確，但推測起因於烯丙基系聚合物(A)之環狀骨架X之結構。
又，於在印刷(尤其是平版印刷)時使用水(例如潤濕水)之情形時，水會混入墨水，但本發明之光硬化性樹脂組成物於不存在水之情形、存在水之情形之任一狀態下，均能夠降低於低頻區域之儲存彈性模數，具有良好之流動性，及/或能夠增大於高頻區域之儲存彈性模數，提高高速印刷中之響應速度，獲得良好之印刷響應性。
並且已知若於用作平版印墨時摻合酞酸二烯丙酯樹脂，則與塑膠基材之密接性會不足。近年來，市售有聚對酞酸乙二酯(PET)、聚丙烯(PP)等各個種類之塑膠製品，要求提高與塑膠基材之密接性(為酞酸
二烯丙酯樹脂之缺陷)。
另一方面，本發明之光硬化性樹脂組成物對塑膠基材之密接性優異，尤其是對PP(聚丙烯)樹脂之密接性優異。又，若含有烯丙基系聚合物(A)及膠化劑(B)，則能夠構成與其他樹脂成分組合之情形時相溶性良好之組成物。故而，本發明之光硬化性樹脂組成物適合作為若為使用有以往之酞酸二烯丙酯樹脂之組成物則難以提高密接性之PP樹脂用墨水、塗料之成分。
由此，本發明之墨水適合作為用以對塑膠基材進行印刷之墨水，尤其適合作為用以對PP樹脂製之片、膜等基材進行印刷之墨水。
又，本發明之塗料適合作為用以對塑膠基材進行繪圖之塗料，尤其適合作為用以對PP樹脂製之片、膜等基材進行繪圖之塗料。
以下，詳細說明本發明。
烯丙基系聚合物(A)
本發明之光硬化性樹脂組成物含有使下述通式(I)表示之烯丙基系化合物進行聚合而獲得之烯丙基系聚合物(A)。
[R1及R2分別表示H或CH3，X表示a價基，該a價基為不具有取代基之飽和或一部分不飽和之4~8員環之環狀骨架，a表示2或3]
作為上述通式(I)中之X之較佳例，可例示以下之環狀骨
架。
作為上述通式(I)中之X之更佳例，可例示以下之環狀骨架。
作為上述通式(I)中之X之進而較佳之例，可例示以下之環狀骨架。
X可為各種，亦可為上述以外之環狀骨架。於環狀骨架為一部分不飽和之情形時，環狀骨架具有之雙鍵之數量並不限定於1，亦可為2以上。其中，X不為芳香族之6員環骨架。
X亦可於分子內交聯，作為於分子內經交聯之X之例，可列舉金剛烷、降莰烯、降
烷等。
X為a價基，a為2或3，故而X為2價或3價基。於X之環狀骨架鍵結有a個(2個或3個)通式(I)中所示之烯丙酯基[-CO-O-CH2-CR2=CHR1]。
X之環上之烯丙酯基[-CO-O-CH2-CR2=CHR1]之取代位置可為任意組合，烯丙基系化合物亦可為具有不同取代位置之組合的物質之混合物。尤其是2個烯丙酯基鍵結於6員環之X時，2個烯丙酯基可為鄰位配向、間位配向或對位配向之任一者，但較佳為鄰位配向或對位配向。
作為上述通式(I)表示之烯丙基系化合物之具體例，可例示：1,2-環己烷二羧酸二烯丙酯、1,3-環己烷二羧酸二烯丙酯、1,4-環己烷二羧酸二烯丙酯、4-環己烯-1,2-二羧酸二烯丙酯、2-環己烯-1,2-二羧酸二烯丙酯等。其中，較佳為1,2-環己烷二羧酸二烯丙酯、4-環己烯-1,2-二羧酸二烯丙酯、1,4-環己烷二羧酸二烯丙酯，更佳為1,2-環己
烷二羧酸二烯丙酯。可將藉由使選自由上述烯丙基系化合物所組成之群中之至少1種以上進行聚合而獲得之烯丙基系聚合物(A)用於光硬化性樹脂組成物。進而，亦可將使上述通式(I)表示之烯丙基系化合物與其他可聚合之化合物進行共聚而得者用於光硬化性樹脂組成物。作為可共聚之化合物，例如可例示：3-甲基-六氫-1,2-酞酸二烯丙酯、4-甲基-六氫-1,2-酞酸二烯丙酯、3-甲基-1,2,3,6-四氫-1,2-酞酸二烯丙酯、4-甲基-1,2,3,6-四氫-1,2-酞酸二烯丙酯等。
作為獲得作為上述通式(I)表示之烯丙基系化合物的具體例而列舉之化合物的方法之例，可列舉使環己烷二羧酸或環己烷二羧酸酐與烯丙醇或氯化烯丙基進行酯化反應之方法，及使環己烯二羧酸或環己烯二羧酸酐與烯丙醇或氯化烯丙基進行酯化反應之方法。
又，亦可使用上述通式(I)表示之烯丙基系化合物之具體例所列舉的化合物之市售品。
上述通式(I)表示之烯丙基系化合物之聚合方法並無特別限定，可使用通常之聚合反應。上述聚合反應中，亦可視需要適當添加聚合起始劑。藉由使用聚合起始劑，能夠於短時間內獲得更高分子量之聚合物。
作為用於烯丙基系化合物之聚合反應中的聚合起始劑，可列舉：偶氮雙異丁腈、2,2'-偶氮雙異丁酸二甲酯等偶氮起始劑；過氧化酮、過氧縮酮、氫過氧化物、過氧化二烷基、過氧化二醯基、過氧化二碳酸酯、過氧酯、過氧化苯甲醯等過氧化物起始劑；2-甲基-1-[4-(甲硫基)苯基]-2-
啉基丙烷-1-酮、1-羥基環己基苯基酮等苯乙酮系；安息香、安
息香乙醚等安息香系；二苯甲酮等二苯甲酮系；醯基氧化膦等磷系；9-氧硫
等硫系；二苯乙二酮、9,10-菲醌等二苯乙二酮系光聚合起始劑。
聚合起始劑之量相對於通式(I)表示之烯丙基系化合物之單體100重量份，較佳為5.0重量份以下，更佳為3.0重量份以下。又，進而較佳為0.001~3.0重量份。
聚合時之反應溫度為60~240℃，例如較佳為80~220℃。反應時間為0.1~100小時，例如較佳為1~30小時。
藉由上述方法等使上述通式(I)表示之烯丙基系化合物進行聚合，藉此能夠製備具有基於上述通式(I)表示之烯丙基系化合物的單體單元的烯丙基系聚合物(A)。
基於上述通式(I)表示之烯丙基系化合物的單體單元之含量於烯丙基系聚合物(A)100重量%中，較佳為20重量%以上，更佳為50重量%以上，進而較佳為80重量%以上，特佳為98重量%以上，亦可為100重量%。
烯丙基系聚合物(A)之重量平均分子量較佳為300,000以下，更佳為200,000以下。又，進而較佳為2,000~150,000，特佳為5,000~140,000。
本發明之光硬化性樹脂組成物中的烯丙基系聚合物(A)之含量相對於光硬化性樹脂組成物總量，較佳為1~60重量%，更佳為2~55重量%，進而較佳為5~50重量%。若為上述範圍內，則即便添加後述之膠化劑(B)或乙烯性不飽和化合物(C)，亦可保持充分溶解之狀態，製成相溶性優異之組成物，更佳地獲得本發明之效果。
膠化劑(B)
本發明中，作為用於含有烯丙基系聚合物(A)之光硬化性樹脂組成物中的膠化劑(B)，只要為藉由與烯丙基系聚合物(A)一同使用而能夠疑似地形成交聯鏈者，則並無特別限定。作為膠化劑(B)，例如可列舉鋁錯合物，可例示：環狀鋁化合物類，例如環狀氧化鋁辛酸鹽(川研精細化學公司製造之Algomer 800)、環狀氧化鋁硬脂酸鹽(川研精細化學公司製造之Algomer 1000S)等；作為烷氧化鋁類之乙氧化鋁、異丙氧化鋁(川研精細化學公司製造之AIPD)、第二丁氧化鋁(川研精細化學公司製造之ASPD)、二異丙氧單第二丁氧化鋁(川研精細化學公司製造之AMD)；鋁乙酸烷基酯類，例如二正丁氧化鋁-乙醯乙酸乙酯(Hope Chemical公司製造之Chelope-AI-EB2)、二異丁氧化鋁-乙醯乙酸甲酯(Hope Chemical公司製造之Chelope-AI-MB12)、二異丁氧化鋁-乙醯乙酸乙酯(Hope Chemical公司製造之Chelope-AI-EB102)、二異丁氧化鋁-乙醯乙酸乙酯(Hope Chemical公司製造之Chelope-AI-EB2)、二異丙氧化鋁-乙醯乙酸乙酯(Hope Chemical公司製造之Chelope-AI-EP12，川研精細化學公司製造之ALCH)、三(乙醯丙酮)鋁(川研精細化學公司製造之ALCH-TR)、三(乙醯丙酮)鋁(川研精細化學公司製造之Alumichelate A)、雙(乙基乙醯丙酮)-單乙醯丙酮鋁(川研精細化學公司製造之Alumichelate D)、Alumichelate M(川研精細化學公司製造)、Alumichelate NB-15(Hope Chemical公司製造)、Chelope S(Hope Chemical公司製造)、Chelope ACS-2(Hope Chemical公司製造)、Liquid Oliepe AOO(Hope Chemical公司製造)、Liquid Oliepe AOS(Hope Chemical公司製造)。作為鋁皂，可例示：硬脂酸鋁(日油股份有限公司製
造)、油酸鋁、環烷酸鋁、尿酸鋁、乙醯丙酮鋁等。
作為其他膠化劑(B)，可例示：環狀二肽類；具有使有機液體凝膠化之性質的伸乙基雙(12-羥基十八酸)醯胺等雙醯胺類；Al-Mg-羥基辛酸鹽、Al-Mg-羥基肉豆蔻酸鹽、Al-Mg-羥基棕櫚酸鹽、Al-Mg-羥基二十二酸(behenate)鹽等粉末狀鋁-鎂化合物。進而可例示：AIP、ASB、AIE-M、ASE-M、OAO、OAO-EF、OAO-HT、Cyco-Gel、Ketalin、Ketalin-II、Ketalin-III、TRI-HLP-49、P-95、KHD、ATC-30、OASMS、OAS/607、ALAC、AO-L47(以上由Chattem Chemicals,Inc)等。進而可例示：鈦酸四異丙酯、鈦酸四正丁酯、四丁氧基鈦、乙醯丙酮鈦、辛二醇鈦、乳酸鈦、乳酸乙酯鈦等有機鈦酸酯等。又，可例示：四丁氧化鋯、四丙氧化鋯、乙醯丙酮丁氧化鋯、乙醯乙酸乙酯丁氧化鋯等烷氧化鋯類；四乙醯丙酮鋯、三丁氧基單乙醯丙酮鋯、二丁氧基二乙醯丙酮鋯、單丁氧基三乙醯丙酮鋯、乙醯乙酸乙酯鋯、氯化鋯化合物、乳酸鋯銨鹽等鋯錯合物等有機鋯等。
膠化劑(B)中，較佳為鋁錯合物、有機鋯，較佳為鋁乙酸烷基酯類、有機鋯，更佳為二異丙氧化鋁-乙醯乙酸乙酯、三(乙醯丙酮)鋁、四丁氧化鋯、四乙醯丙酮鋯、乙醯丙酮丁氧化鋯。
光硬化性樹脂組成物所含有的膠化劑(B)之含量相對於光硬化性樹脂組成物的烯丙基系聚合物(A)100重量份，較佳為0.1~10重量份，更佳為0.5~5重量份，特佳為1~3重量份。若為上述範圍內，則可更佳地獲得本發明之效果。又，可獲得與塑膠基材充分之密接性，且保持烯丙基系聚合物(A)與膠化劑(B)充分溶解之狀態，成為相溶性優異之
組成物。進而，即便添加乙烯性不飽和化合物(C)，亦可保持充分溶解之狀態。
乙烯性不飽和化合物(C)
本發明之光硬化性樹脂組成物較佳含有藉由光照射而可硬化之乙烯性不飽和化合物(C)。乙烯性不飽和化合物(C)較佳具有1~20個碳-碳雙鍵，更佳具有1~10個，進而較佳具有2~6個。作為乙烯性不飽和化合物(C)，可列舉(甲基)丙烯酸酯化合物、(甲基)烯丙基化合物及乙烯基化合物等。又，乙烯性不飽和化合物亦可使用2種以上之化合物的混合物。
作為(甲基)丙烯酸酯化合物，可例示：新戊四醇、二新戊四醇、三羥甲丙烷、二-三羥甲丙烷、新戊二醇、1,6-己二醇、甘油、聚乙二醇、聚丙二醇等醇類之(甲基)丙烯酸酯化合物，及對該等加成環氧乙烷、環氧丙烷等環氧烷而得之(甲基)丙烯酸酯化合物；對雙酚A、雙酚F等雙酚類加成環氧乙烷、環氧丙烷等環氧烷而得者之(甲基)丙烯酸酯化合物；環氧(甲基)丙烯酸酯、胺酯(甲基)丙烯酸酯、醇酸(甲基)丙烯酸酯等(甲基)丙烯酸酯化合物；環氧化大豆油丙烯酸酯等(甲基)丙烯酸酯化合物；較佳為新戊四醇、二新戊四醇、三羥甲丙烷、二-三羥甲丙烷、新戊二醇、1,6-己二醇、甘油、聚乙二醇、聚丙二醇等醇類之(甲基)丙烯酸酯化合物，及對該等加成環氧乙烷、環氧丙烷等環氧烷而得之(甲基)丙烯酸酯化合物，更佳為新戊四醇、二新戊四醇、三羥甲丙烷、二-三羥甲丙烷等醇類之(甲基)丙烯酸酯化合物，及對該等加成環氧乙烷、環氧丙烷等環氧烷而得之(甲基)丙烯酸酯化合物。
作為(甲基)烯丙基化合物，可例示酞酸二(甲基)烯丙酯、三
聚異氰酸三(甲基)烯丙酯等。
作為乙烯基化合物，可例示苯乙烯、二乙烯苯、N-乙烯基吡咯啶酮、乙酸乙烯酯等。
其中，就與烯丙基系聚合物(A)之相溶性、光硬化時之硬化性之方面而言，較佳為二-三羥甲丙烷四丙烯酸酯、三羥甲丙烷三丙烯酸酯、二新戊四醇六丙烯酸酯，更佳為二-三羥甲丙烷四丙烯酸酯。
本發明之光硬化性樹脂組成物所含有之乙烯性不飽和化合物(C)的含量相對於光硬化性樹脂組成物中之烯丙基系聚合物(A)100重量份，較佳為50~1000重量份，更佳為50~400重量份，進而較佳為50~300重量份。
又，光硬化性樹脂組成物所含有之乙烯性不飽和化合物(C)之含量較佳以光硬化性樹脂組成物之黏度在100~500Pa‧s(25℃)之範圍內之方式添加。
其他添加物
本發明之光硬化性樹脂組成物亦可含有聚合起始劑，尤其較佳含有光聚合起始劑。作為光硬化性樹脂組成物所含有之光聚合起始劑，可列舉：2-甲基-1-[4-(甲硫基)苯基]-2-
啉基丙烷-1-酮、1-羥基環己基苯基酮等苯乙酮系；安息香、安息香乙醚等安息香系；二苯甲酮等二苯甲酮系；醯基氧化膦等磷系；9-氧硫
等硫系；二苯乙二酮、9,10-菲醌等二二苯乙二酮系。
光硬化性樹脂組成物所含有的光聚合起始劑之量相對於光硬化性樹脂組成物整體，較佳為0.1~15重量%之範圍，更佳為0.5~12重
量%之範圍，進而較佳為1~10重量%之範圍。
光硬化性樹脂組成物中亦可併用光起始助劑(例如三乙醇胺等胺系光起始助劑)。
光起始助劑之量相對於光硬化性樹脂組成物整體，較佳為0.1~5重量%之範圍，更佳為0.5~3重量%之範圍。
本發明之光硬化性樹脂組成物可視目的而含有如下例示之各種添加劑：穩定劑(例如對苯二酚、對甲氧基苯酚等聚合抑制劑)、顏料(例如花青藍、雙偶氮黃、胭脂紅6b、色澱紅C(Lake Red C)、碳黑、鈦白)等著色劑、填充劑、黏度調整劑(例如蠟)等。光硬化性樹脂組成物所含有的穩定劑之量相對於光硬化性樹脂組成物整體，較佳為0.01~2重量%之範圍，更佳為0.1~1重量%之範圍。
著色劑之量相對於光硬化性樹脂組成物整體，較佳為1~50重量%之範圍，更佳為1~45重量%之範圍。
本發明之光硬化性樹脂組成物較佳為：相較於未摻合膠化劑(B)之光硬化性樹脂組成物，藉由摻合膠化劑(B)，而使0.01Hz(低頻區域)之儲存彈性模數較佳在70%以下，更佳在50%以下，進而較佳在40%以下。藉此，可獲得更加良好之流動性。
又，本發明之光硬化性樹脂組成物較佳為：相較於未摻合膠化劑(B)之光硬化性樹脂組成物，藉由摻合膠化劑(B)，而使10Hz(高頻區域)之儲存彈性模數較佳在120%以上，更佳在150%以上。藉此，可獲得更加良好之印刷響應性。
此處，儲存彈性模數係藉由實施例所記載之方法而測量之值。
本發明之光硬化性樹脂組成物可藉由向烯丙基系聚合物(A)加入膠化劑(B)，並視需要混入乙烯性不飽和化合物(C)、進而光聚合起始劑、光起始助劑、添加劑(例如穩定劑、顏料)而製造。本發明之光硬化性樹脂組成物藉由照射光而硬化。用於硬化之光一般為紫外線。
光硬化性樹脂組成物之硬化反應中所使用的硬化裝置或硬化條件並無特別限定，只要是通常之光硬化反應中所用之方法即可。
本發明之光硬化性樹脂組成物之用途並無特別限定。可於墨水(例如光硬化性平版用印刷墨水、絲網墨水、凹版墨水等印刷墨水)、塗料(例如紙用、塑膠用、金屬用、木工用等塗料，可例示罩光漆)、接著劑、光阻劑等技術領域中使用。
含有本發明之光硬化性樹脂組成物的墨水為本發明之墨水，含有本發明之光硬化性樹脂組成物的塗料為本發明之塗料。又，本發明之塗料較佳為罩光漆。
例如，墨水之通常的製作方法如下所示。一面以60℃~120℃之溫度進行攪拌一面使烯丙基系聚合物(A)、膠化劑(B)及穩定劑等溶解於乙烯性不飽和化合物(C)，而製作清漆。以蝶形攪拌器將顏料、光聚合起始劑、其他添加劑攪拌混合於該清漆後，以三輥研磨機等進行研磨，藉此獲得墨水。
又，罩光漆之製成除不使用顏料以外，可藉由與墨水相同之順序進行。
(實施例)
以下，列舉實施例更加具體地說明本發明，但本發明並不限定於該等實施例。
烯丙基系聚合物之重量平均分子量(Mw)、分子量分佈(Mw/Mn)之測量
重量平均分子量(Mw)、分子量分佈(Mw/Mn)係使用GPC而測量。為標準聚苯乙烯換算之重量平均分子量之值。
管柱：將ShodexKF-806L、KF-804、KF-803、KF-802、KF-801串聯連接
流速：1.0mL/min
溫度：40℃
檢測：RID-6A
試樣：將試樣20mg溶解於四氫呋喃10mL而製成測量用之樣品。
製造例1 1,2-環己烷二羧酸二烯丙酯聚合物之合成
1,2-環己烷二羧酸二烯丙酯係藉由使環己烷二羧酸酐與烯丙醇進行酯化反應而製造。
向3L之可分離式燒瓶中加入1,2-環己烷二羧酸二烯丙酯2400g，並加入60g之過氧化苯甲醯，以80℃進行加熱攪拌。反應2.5小時後，冷卻至30℃。冷卻後，向燒瓶加入甲醇，使聚合物沈澱。將所獲得之聚合物以40℃進行減壓乾燥16小時(產量：408g，產率：17%，Mw=32,000、Mw/Mn=2.8)。將所獲得之聚合物設為聚合物1。
(實施例1、2)
(1)清漆之製備
以樹脂(上述聚合物1)35重量份、DTMPTA(SR-355NS：Sartomer公司製造之二-三羥甲丙烷四丙烯酸酯)65重量份、聚合抑制劑(IRGANOX
1076：BASF Japan股份有限公司製造之3-(3,5-二-第三丁基-4-羥基苯基)丙酸十八烷基酯)0.3重量份之比率進行添加，以100℃使其熱熔而製備微淡黃色透明之清漆。
(2)凝膠清漆之製備
對(1)中所製備之清漆100重量份，添加膠化劑(ALCH：川研精細化學公司製造之二異丙氧化鋁-乙醯乙酸乙酯(鋁錯合物))0.6重量份(實施例1)、膠化劑(ORGATIX ZC-150：松本精細化學公司製造之四乙醯丙酮鋯(有機鋯))1.0重量份(實施例2)，以110℃攪拌1小時而製備透明之凝膠清漆。
(3)墨水之製備
光硬化性墨水之製備方法
將上述(2)中所製備之凝膠清漆62.6重量份、二-三羥甲丙烷四丙烯酸酯(DTMPTA)10.4重量份、聚乙烯蠟2重量份、光聚合起始劑(Irgacure 907：BASF Japan股份有限公司製造，2-甲基-1-[4-(甲硫基)苯基]-2-
啉基丙烷-1-酮)5重量份、顏料(酞菁藍)20重量份以三輥研磨機進行研磨而製備墨水。
(比較例1)
除使用(1)中所製備之清漆代替凝膠清漆(上述(2)中所製備之凝膠清漆)外，藉由與實施例1、2相同之方法製備墨水。
(動態黏彈性測量)
使用所製備之實施例1、2及比較例1之墨水進行動態黏彈性測量，測量儲存彈性模數。再者，關於假定混入水之情形之「乳化後之」試驗，在
對墨水100重量份添加100重量份水後，藉由分散機攪拌混合3分鐘，製備乳化後之墨水，使用乳化後之墨水進行黏弾性試驗。
(動態黏彈性測量之條件)
藉由HAAKE MARS III黏弾性測量裝置(Thermo Scientific公司製造)，使用直徑35mm、圓錐角度2度之錐板，以25℃進行頻率掃描測量。
所測量之儲存彈性模數係將比較例1之結果設為100而顯示指數，將評價結果示於表1。指數越大，表示儲存彈性模數越大。
(黏度測量)
關於所製備之凝膠清漆、清漆，使用BROOKFIELD VISCOMETER DV-II+Pro測量25℃之黏度(Pa‧s)。將評價結果示於表1。
由表1可知，含有使具有特定結構之烯丙基系化合物進行聚合而獲得之烯丙基系聚合物(A)、膠化劑(B)之實施例1於不存在水之情形(乳化前)、存在水之情形(乳化後)之任一狀態，均能夠降低於低頻區域之儲存彈性模數，具有良好之流動性，且可增大於高頻區域之儲存彈性
模數，提高高速印刷中之響應速度，獲得良好之印刷響應性。又，實施例2於不存在水之情形(乳化前)、存在水之情形(乳化後)之任一狀態，均能夠降低於低頻區域之儲存彈性模數，具有良好之流動性。即，可知藉由併用烯丙基系聚合物(A)、膠化劑(B)，能夠獲得良好之流動性及/或印刷響應性，印刷適應性優異，可較佳地用作墨水。
又，可知藉由添加膠化劑，清漆之黏度提高，可增大於高頻區域之儲存彈性模數，藉由在含有烯丙基系聚合物(A)之同時含有膠化劑(B)，疑似地形成交聯鏈。進而可知，實施例1之凝膠清漆之外觀為無色透明，實施例2之凝膠清漆之外觀為淡黃色透明，可較佳地用於墨水(例如平版印墨)、塗料、接著劑、光阻劑等。
[產業上之可利用性]
本發明之光硬化性樹脂組成物可用於墨水(例如平版印墨)、塗料、接著劑、光阻劑等(尤其是作為塑膠基材用)。
Claims (6)
- 一種光硬化性樹脂組成物，含有使下述通式(I)表示之烯丙基系化合物進行聚合而獲得之烯丙基系聚合物(A)及膠化劑(B)，該膠化劑(B)為鋁錯合物、有機鋯、或有機鈦酸酯，
- 如申請專利範圍第1項之光硬化性樹脂組成物，其進而含有乙烯性不飽和化合物(C)。
- 如申請專利範圍第1或2項之光硬化性樹脂組成物，其進而含有光聚 合起始劑。
- 一種墨水，其含有申請專利範圍第1至3項中任一項之光硬化性樹脂組成物。
- 一種塗料，其含有申請專利範圍第1至3項中任一項之光硬化性樹脂組成物。
- 如申請專利範圍第5項之塗料，其為罩光漆。
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| CN101279913A (zh) * | 2000-06-16 | 2008-10-08 | 昭和电工株式会社 | 生产用于塑料透镜组合物的脂环族(甲基)烯丙酯的方法 |
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| EP3438190A1 (en) | 2019-02-06 |
| ES2818899T3 (es) | 2021-04-14 |
| US10941232B2 (en) | 2021-03-09 |
| KR102230846B1 (ko) | 2021-03-22 |
| CN108699314B (zh) | 2021-07-06 |
| JPWO2017170388A1 (ja) | 2019-02-07 |
| EP3438190A4 (en) | 2019-10-23 |
| WO2017170388A1 (ja) | 2017-10-05 |
| EP3438190B1 (en) | 2020-09-02 |
| JP6860002B2 (ja) | 2021-04-14 |
| CN108699314A (zh) | 2018-10-23 |
| TW201806983A (zh) | 2018-03-01 |
| US20190085111A1 (en) | 2019-03-21 |
| KR20180123013A (ko) | 2018-11-14 |
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