JP6066027B1 - Radical polymerizable resin composition and civil engineering primer - Google Patents
Radical polymerizable resin composition and civil engineering primer Download PDFInfo
- Publication number
- JP6066027B1 JP6066027B1 JP2016559370A JP2016559370A JP6066027B1 JP 6066027 B1 JP6066027 B1 JP 6066027B1 JP 2016559370 A JP2016559370 A JP 2016559370A JP 2016559370 A JP2016559370 A JP 2016559370A JP 6066027 B1 JP6066027 B1 JP 6066027B1
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- JP
- Japan
- Prior art keywords
- resin composition
- materials
- radical polymerizable
- polymerizable resin
- cyclodextrin
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 36
- 238000007605 air drying Methods 0.000 claims abstract description 27
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 24
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 229920006305 unsaturated polyester Polymers 0.000 claims description 10
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 claims description 7
- 238000010276 construction Methods 0.000 claims description 6
- -1 articles Substances 0.000 abstract description 24
- 239000000463 material Substances 0.000 abstract description 24
- 239000011248 coating agent Substances 0.000 abstract description 9
- 238000000576 coating method Methods 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000007924 injection Substances 0.000 abstract description 4
- 238000002347 injection Methods 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract description 3
- 230000001070 adhesive effect Effects 0.000 abstract description 3
- 239000004566 building material Substances 0.000 abstract description 3
- 238000009408 flooring Methods 0.000 abstract description 3
- 239000003973 paint Substances 0.000 abstract description 3
- 239000013615 primer Substances 0.000 abstract description 3
- 239000002987 primer (paints) Substances 0.000 abstract description 3
- 239000003566 sealing material Substances 0.000 abstract description 3
- 238000004078 waterproofing Methods 0.000 abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 26
- 150000003254 radicals Chemical class 0.000 description 26
- 239000004793 Polystyrene Substances 0.000 description 16
- 229920002223 polystyrene Polymers 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- 239000002253 acid Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 9
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical group C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- POYODSZSSBWJPD-UHFFFAOYSA-N 2-methylprop-2-enoyloxy 2-methylprop-2-eneperoxoate Chemical compound CC(=C)C(=O)OOOC(=O)C(C)=C POYODSZSSBWJPD-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000012169 petroleum derived wax Substances 0.000 description 5
- 235000019381 petroleum wax Nutrition 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 4
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000006136 alcoholysis reaction Methods 0.000 description 3
- 239000010426 asphalt Substances 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
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YZOUYRAONFXZSI-SBHWVFSVSA-N (1S,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31S,33R,35R,36R,37S,38R,39S,40R,41S,42R,43S,44R,45S,46R,47S,48R,49S)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-37,39,40,41,42,43,44,45,46,47,48,49-dodecamethoxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,38-diol Chemical compound O([C@@H]([C@H]([C@@H]1OC)OC)O[C@H]2[C@@H](O)[C@@H]([C@@H](O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3O)OC)O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3OC)OC)O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3OC)OC)O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3OC)OC)O3)O[C@@H]2CO)OC)[C@H](CO)[C@H]1O[C@@H]1[C@@H](OC)[C@H](OC)[C@H]3[C@@H](CO)O1 YZOUYRAONFXZSI-SBHWVFSVSA-N 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 2
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical group CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000001116 FEMA 4028 Substances 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
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229960004853 betadex Drugs 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N butane-1,2,3,4-tetrol Chemical compound OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
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- 150000007519 polyprotic acids Polymers 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-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
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- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 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
- JFZVSHAMRZPOPA-UHFFFAOYSA-N 1-[n-(2-hydroxypropyl)-4-methylanilino]propan-2-ol Chemical compound CC(O)CN(CC(C)O)C1=CC=C(C)C=C1 JFZVSHAMRZPOPA-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-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
- JHSWSKVODYPNDV-UHFFFAOYSA-N 2,2-bis(prop-2-enoxymethyl)propane-1,3-diol Chemical compound C=CCOCC(CO)(CO)COCC=C JHSWSKVODYPNDV-UHFFFAOYSA-N 0.000 description 1
- JMIZWXDKTUGEES-UHFFFAOYSA-N 2,2-di(cyclopenten-1-yloxy)ethyl 2-methylprop-2-enoate Chemical compound C=1CCCC=1OC(COC(=O)C(=C)C)OC1=CCCC1 JMIZWXDKTUGEES-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
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- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 1
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- IGDCJKDZZUALAO-UHFFFAOYSA-N 2-prop-2-enoxypropane-1,3-diol Chemical compound OCC(CO)OCC=C IGDCJKDZZUALAO-UHFFFAOYSA-N 0.000 description 1
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- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- FYRWKWGEFZTOQI-UHFFFAOYSA-N 3-prop-2-enoxy-2,2-bis(prop-2-enoxymethyl)propan-1-ol Chemical compound C=CCOCC(CO)(COCC=C)COCC=C FYRWKWGEFZTOQI-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- JOCUIVLSLBBESN-UHFFFAOYSA-N 4-[2-hydroxyethyl(methyl)amino]benzaldehyde Chemical compound OCCN(C)C1=CC=C(C=O)C=C1 JOCUIVLSLBBESN-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000004992 toluidines Chemical class 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
Abstract
空気乾燥性不飽和樹脂（Ａ）、ラジカル重合性単量体（Ｂ）、並びに、シクロデキストリン及び／又はその誘導体（Ｃ）を含有することを特徴とするラジカル重合性樹脂組成物を提供する。本発明のラジカル重合性樹脂組成物は、工場、倉庫、クリーンルーム等の床材；舗装材、防水材、塗料、プライマー、壁面コーティング材、道路マーキング材、注入材、シール材、注型品、積層品、接着剤、ライニング材、波平板等の土木建築材料の製造に好適に使用することができ、土木建築用プライマーとして特に好適に使用することができる。Provided is a radical polymerizable resin composition comprising an air-drying unsaturated resin (A), a radical polymerizable monomer (B), and cyclodextrin and / or a derivative thereof (C). The radical polymerizable resin composition of the present invention is a flooring material for factories, warehouses, clean rooms, etc .; paving materials, waterproofing materials, paints, primers, wall coating materials, road marking materials, injection materials, sealing materials, cast products, laminates It can be suitably used for the production of civil engineering and building materials such as articles, adhesives, lining materials and corrugated plates, and can be particularly suitably used as a civil engineering and building primer.
Description
本発明は、表面乾燥性及び湿潤面に対する接着性に優れるラジカル重合性樹脂組成物に関する。 The present invention relates to a radical polymerizable resin composition having excellent surface drying properties and adhesion to wet surfaces.
昨今、増加する交通荷重や凍結防止剤の散布によって、高速道路をはじめとする道路橋床版の早期劣化が顕著となってきている。この早期劣化のメカニズムとしては、アスファルト舗装と鉄筋コンクリート床版に生じたひび割れを通じて、雨水、凍結防止剤などが構造物に侵入し鉄筋を腐食させ、構造物の耐久性を低下させていることが考えられている。 In recent years, early deterioration of road bridge decks including highways has become remarkable due to increasing traffic loads and spraying of antifreezing agents. As a mechanism for this early deterioration, it is thought that rainwater, anti-freezing agents, etc. penetrate into the structure through the cracks generated in asphalt pavement and reinforced concrete floor slabs, corrode the reinforcing bars and reduce the durability of the structure. It has been.
これら道路橋床版の耐久性を向上する手法としては、床版層、防水材層、及び、アスファルト舗装層が順次積層された床版防水構造体が各種検討されている。 As a technique for improving the durability of these road bridge decks, various floor slab waterproof structures in which a floor slab layer, a waterproof material layer, and an asphalt pavement layer are sequentially laminated have been studied.
前記床版防水構造体としては、例えば、床版層、ウレタン防水材層、ウレタン接着剤層、及び、アスファルト舗装層が順次積層された床版防水構造体が開示されている（例えば、特許文献１を参照。）。前記接着剤層に使用されるウレタン樹脂はコストが安価であることから日本における普及度は高いものの、表面乾燥性が遅く工期の短縮化が望まれている。また、施工時に防水材層が雨で濡れる場合や多湿な環境で使用された場合に、所望の接着性が得られないとの問題もあった。 As the floor slab waterproof structure, for example, a floor slab waterproof structure in which a floor slab layer, a urethane waterproof material layer, a urethane adhesive layer, and an asphalt pavement layer are sequentially laminated is disclosed (for example, Patent Documents). 1). The urethane resin used for the adhesive layer is low in cost, and thus is highly popular in Japan, but its surface dryness is slow and shortening of the construction period is desired. In addition, there has been a problem that the desired adhesiveness cannot be obtained when the waterproof material layer is wetted by rain during construction or when used in a humid environment.
本発明が解決しようとする課題は、表面乾燥性及び湿潤面に対する接着性に優れるラジカル重合性樹脂組成物を提供することである。 The problem to be solved by the present invention is to provide a radically polymerizable resin composition having excellent surface drying properties and adhesion to wet surfaces.
本発明は、空気乾燥性不飽和樹脂（Ａ）、ラジカル重合性単量体（Ｂ）、並びに、シクロデキストリン及び／又はその誘導体（Ｃ）を含有することを特徴とするラジカル重合性樹脂組成物を提供するものである。 The present invention relates to a radically polymerizable resin composition comprising an air-drying unsaturated resin (A), a radically polymerizable monomer (B), and cyclodextrin and / or a derivative thereof (C). Is to provide.
また、本発明は、前記ラジカル重合性樹脂組成物からなる土木建築用プライマーを提供するものである。 Moreover, this invention provides the primer for civil engineering construction which consists of the said radically polymerizable resin composition.
本発明のラジカル重合性樹脂組成物は、表面乾燥性及び湿潤面に対する接着性（以下、「湿潤面接着性」と略記する。）に優れるものである。従って、本発明のラジカル重合性樹脂組成物は、工場、倉庫、クリーンルーム等の床材；舗装材、防水材、塗料、プライマー、壁面コーティング材、道路マーキング材、注入材、シール材、注型品、積層品、接着剤、ライニング材、波平板等の土木建築材料の製造に好適に使用することができ、土木建築用プライマーとして特に好適に使用することができる。 The radical polymerizable resin composition of the present invention is excellent in surface drying property and adhesion to a wet surface (hereinafter abbreviated as “wet surface adhesion”). Therefore, the radically polymerizable resin composition of the present invention is used for flooring materials such as factories, warehouses, and clean rooms; paving materials, waterproofing materials, paints, primers, wall coating materials, road marking materials, injection materials, sealing materials, and cast products. It can be suitably used for the production of civil engineering and building materials such as laminates, adhesives, lining materials and corrugated plates, and can be particularly suitably used as a primer for civil engineering and construction.
本発明のラジカル重合性樹脂組成物は、空気乾燥性不飽和樹脂（Ａ）、ラジカル重合性単量体（Ｂ）、並びに、シクロデキストリン及び／又はその誘導体（Ｃ）を必須成分として含有するものである。 The radical polymerizable resin composition of the present invention contains air-drying unsaturated resin (A), radical polymerizable monomer (B), and cyclodextrin and / or its derivative (C) as essential components. It is.
本発明のラジカル重合性樹脂組成物が優れた表面乾燥性及び湿潤面接着性を両立する機序としては、前記空気乾燥性不飽和樹脂（Ａ）が有する空気乾燥性成分が大気中の酸素を利用して酸化重合を起こすため、ラジカル重合を阻害せず塗膜の硬化不良が抑制されること、及び、前記シクロデキストリン及び／又はその誘導体（Ｃ）が塗膜下部に沈降しやすく、湿潤した被着面と強力な分子間力による相互作用が働くことが考えられる。 As a mechanism in which the radically polymerizable resin composition of the present invention achieves both excellent surface drying properties and wet surface adhesiveness, the air drying component of the air drying unsaturated resin (A) is responsible for oxygen in the atmosphere. Oxidation polymerization is used to prevent radical polymerization from being inhibited and poor curing of the coating is suppressed, and the cyclodextrin and / or its derivative (C) easily settles under the coating and is wet. It is thought that the interaction by the adhesion surface and strong intermolecular force works.
前記空気乾燥性不飽和樹脂（Ａ）は、空気乾燥性付与基を有する化合物を原料として得られたものであり、例えば、空気乾燥性不飽和ポリエステル、空気乾燥性ポリエステル（メタ）アクリレート、空気乾燥性エポキシ（メタ）アクリレート、空気乾燥性ウレタン（メタ）アクリレート等を用いることができる。これらの樹脂は単独で用いても２種以上を併用してもよい。 The air-drying unsaturated resin (A) is obtained using a compound having an air-drying imparting group as a raw material. For example, the air-drying unsaturated polyester, air-drying unsaturated polyester (meth) acrylate, air-drying Epoxy (meth) acrylate, air-drying urethane (meth) acrylate, and the like can be used. These resins may be used alone or in combination of two or more.
前記空気乾燥性付与基を有する化合物としては、例えば、環状不飽和脂肪族多塩基酸及びその誘導体を含む化合物、α位水素を有するアリルエーテル基を含む化合物、多価アルコールと乾性油とのエステル交換反応で得られるアルコリシス化合物、水酸基を有するジシクロペンタジエニル基を含む化合物等を用いることができる。これらの化合物は単独で用いても２種以上を併用してもよい。これらの化合物を前記空気乾燥性不飽和樹脂（Ａ）の製造時にエステル化反応及び／又はウレタン化反応させることにより、樹脂骨格に空気乾燥性付与成分を導入することができる。 Examples of the compound having an air drying property-imparting group include a compound containing a cyclic unsaturated aliphatic polybasic acid and a derivative thereof, a compound containing an allyl ether group having an α-position hydrogen, and an ester of a polyhydric alcohol and a drying oil. An alcoholysis compound obtained by an exchange reaction, a compound containing a dicyclopentadienyl group having a hydroxyl group, or the like can be used. These compounds may be used alone or in combination of two or more. By subjecting these compounds to an esterification reaction and / or a urethanization reaction during the production of the air-drying unsaturated resin (A), an air-drying imparting component can be introduced into the resin skeleton.
前記環状不飽和脂肪族多塩基酸及びその誘導体を含む化合物としては、例えば、テトラヒドロ無水フタル酸、エンドメチレンテトラヒドロ無水フタル酸、メチルテトラヒドロ無水フタル酸、α−テルヒネン・無水マレイン酸付加物、トランス−ピペリレン・無水マレイン酸付加物等を用いることができる。これらの化合物は単独で用いても２種以上を併用してもよい。 Examples of the compound containing the cyclic unsaturated aliphatic polybasic acid and derivatives thereof include tetrahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, α-terhinene / maleic anhydride adduct, trans- Piperylene / maleic anhydride adducts can be used. These compounds may be used alone or in combination of two or more.
前記α位水素を有するアリルエーテル基を含む化合物としては、例えば、エチレングリコールモノアリルエーテル、ジエチレングリコールモノアリルエーテル、トリエチレングリコールモノアリルエーテル、ポリエチレングリコールモノアリルエーテル、プロピレングリコールモノアリルエーテル、ジプロピレングリコールモノアリルエーテル、トリプロピレングリコールモノアリルエーテル、ポリプロピレングリコールモノアリルエーテル、１，２−ブチレングリコールモノアリルエーテル、１，３−ブチレングリコールモノアリルエーテル、トリメチロールプロパンモノアリルエーテル、トリメチロールプロパンジアリルエーテル、グリセリンモノアリルエーテル、グリセリンジアリルエーテル、ペンタエリスリトールモノアリルエーテル、ペンタエリスリトールジアリルエーテル、ペンタエリスリトールトリアリルエーテル等の多価アルコールのアリルエーテル化合物；アリルグリシジルエーテル等のオキシラン環を有するアリルエーテル化合物などを用いることができる。これらの化合物は単独で用いても２種以上を併用してもよい。 Examples of the compound containing an allyl ether group having an α-position hydrogen include ethylene glycol monoallyl ether, diethylene glycol monoallyl ether, triethylene glycol monoallyl ether, polyethylene glycol monoallyl ether, propylene glycol monoallyl ether, and dipropylene glycol. Monoallyl ether, tripropylene glycol monoallyl ether, polypropylene glycol monoallyl ether, 1,2-butylene glycol monoallyl ether, 1,3-butylene glycol monoallyl ether, trimethylolpropane monoallyl ether, trimethylolpropane diallyl ether, Glycerol monoallyl ether, glyceryl diallyl ether, pentaerythritol monoallylate , Pentaerythritol diallyl ether, allyl ether compound of a polyhydric alcohol such as pentaerythritol triallyl ether; can be used allyl ether compound having an oxirane ring, such as allyl glycidyl ether and the like. These compounds may be used alone or in combination of two or more.
前記アルコリシス化合物を製造する際に用いる前記多価アルコールとしては、例えば、グリセリン、トリメチロールエタン、トリメチロールプロパン、トリスヒドロキシメチルアミノメタン等の３価のアルコールや、ペンタエリスリトール等の４価のアルコールなどを用いることができる。これらのアルコールは単独で用いても２種以上を併用してもよい。 Examples of the polyhydric alcohol used in producing the alcoholysis compound include trivalent alcohols such as glycerin, trimethylolethane, trimethylolpropane, and trishydroxymethylaminomethane, and tetravalent alcohols such as pentaerythritol. Can be used. These alcohols may be used alone or in combination of two or more.
また、前記アルコリシス化合物を製造する際に用いる前記乾性油としては、例えば、アマニ油、大豆油、綿実油、落花生油、やし油等を用いることができる。これらの乾性油は単独で用いても２種以上を併用してもよい。 Moreover, as said dry oil used when manufacturing the said alcoholysis compound, linseed oil, soybean oil, cottonseed oil, peanut oil, a coconut oil etc. can be used, for example. These drying oils may be used alone or in combination of two or more.
前記水酸基を有するジシクロペンタジエニル基を含む化合物としては、例えば、ジシクロぺンテニルオキシメタノール、ジシクロペンテニルオキシエタノール、ジシクロペンテニルオキシプロパノール等を用いることができる。これらの化合物は単独で用いても２種以上を併用してもよい。 Examples of the compound containing a dicyclopentadienyl group having a hydroxyl group include dicyclopentenyloxymethanol, dicyclopentenyloxyethanol, dicyclopentenyloxypropanol, and the like. These compounds may be used alone or in combination of two or more.
前記空気乾燥性不飽和樹脂（Ａ）としては、後述する（Ｃ）成分との優れた相溶性を示し、ラジカル重合性樹脂組成物を低粘度化させ、塗工作業性を一層向上できる点から、空気乾燥性不飽和ポリエステルを用いることが好ましく、ジシクロペンタジエニル基を有する不飽和ポリエステルを用いることがより好ましい。 The air-drying unsaturated resin (A) has excellent compatibility with the later-described component (C), lowers the viscosity of the radical polymerizable resin composition, and can further improve the coating workability. It is preferable to use an air-drying unsaturated polyester, and it is more preferable to use an unsaturated polyester having a dicyclopentadienyl group.
前記空気乾燥性不飽和ポリエステルとしては、例えば、前記空気乾燥性付与基を有する化合物、α，β−不飽和二塩基酸を含む二塩基酸、及び、多価アルコールをエステル化反応させて得られるものを用いることができる。 The air-drying unsaturated polyester is obtained, for example, by esterifying the compound having the air-drying property-imparting group, a dibasic acid containing an α, β-unsaturated dibasic acid, and a polyhydric alcohol. Things can be used.
前記α，β−不飽和二塩基酸としては、例えば、マレイン酸、無水マレイン酸、フマル酸、イタコン酸、無水イタコン酸等を用いることができる。これらの二塩基酸は単独で用いても２種以上を併用してもよい。 Examples of the α, β-unsaturated dibasic acid include maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, and the like. These dibasic acids may be used alone or in combination of two or more.
前記α，β−不飽和二塩基酸以外に用いることができる二塩基酸としては、飽和二塩基酸を用いることができ、例えば、フタル酸、無水フタル酸、ハロゲン化無水フタル酸、イソフタル酸、テレフタル酸、テトラヒドロフタル酸、テトラヒドロ無水フタル酸、ヘキサヒドロフタル酸、ヘキサヒドロ無水フタル酸、ヘキサヒドロテレフタル酸、ヘキサヒドロイソフタル酸、コハク酸、マロン酸、グルタル酸、アジピン酸、セバシン酸、１，１２−ドデカン２酸，２，６−ナフタレンジカルボン酸、２，７−ナフタレンジカルボン酸、２，３−ナフタレンジカルボン酸、２，３−ナフタレンジカルボン酸無水物、４，４’−ビフェニルジカルボン酸、またこれらのジアルキルエステル等を用いることができる。これらの二塩基酸は単独で用いても２種以上を併用してもよい。 As the dibasic acid that can be used in addition to the α, β-unsaturated dibasic acid, a saturated dibasic acid can be used. For example, phthalic acid, phthalic anhydride, halogenated phthalic anhydride, isophthalic acid, Terephthalic acid, tetrahydrophthalic acid, tetrahydrophthalic anhydride, hexahydrophthalic acid, hexahydrophthalic anhydride, hexahydroterephthalic acid, hexahydroisophthalic acid, succinic acid, malonic acid, glutaric acid, adipic acid, sebacic acid, 1,12 -Dodecane diacid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic anhydride, 4,4'-biphenyldicarboxylic acid, and these The dialkyl ester or the like can be used. These dibasic acids may be used alone or in combination of two or more.
前記多価アルコールとしては、例えば、エチレングリコ−ル、ジエチレングリコ−ル、トリエチレングリコ−ル、ポリエチレングリコ−ル、プロピレングリコ−ル、ジプロピレングリコ−ル、ポリプロピレングリコ−ル、２−メチル−１，３−プロパンジオ−ル、１，３−ブタンジオ−ル、ネオペンチルグリコ−ル、水素化ビスフェノ−ルＡ、１，４−ブタンジオ−ル、ビスフェノ−ルＡのアルキレンオキサイド付加物、１，２，３，４−テトラヒドロキシブタン、グリセリン、トリメチロ−ルプロパン、１，３−プロパンジオ−ル、１，２−シクロヘキサングリコ−ル、１，３−シクロヘキサングリコ−ル、１，４−シクロヘキサングリコ−ル、１，４−シクロヘキサンジメタノ−ル、パラキシレングリコ−ル、ビシクロヘキシル−４，４’−ジオ−ル、２，６−デカリングリコ−ル、２，７−デカリングリコ−ル等を用いることができる。これらの多価アルコールは単独で用いても２種以上を併用してもよい。 Examples of the polyhydric alcohol include ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, and 2-methyl-1. 1,3-propanediol, 1,3-butanediol, neopentyl glycol, hydrogenated bisphenol A, 1,4-butanediol, alkylene oxide adduct of bisphenol A, 1,2 , 3,4-tetrahydroxybutane, glycerin, trimethylolpropane, 1,3-propanediol, 1,2-cyclohexane glycol, 1,3-cyclohexane glycol, 1,4-cyclohexane glycol 1,4-cyclohexanedimethanol, paraxylene glycol, bicyclohexyl-4,4 - Geo - le, 2,6-decalin glycolate - le, 2,7-decalin glyco - can be used Le like. These polyhydric alcohols may be used alone or in combination of two or more.
前記空気乾燥性不飽和樹脂（Ａ）の数平均分子量としては、良好な機械的強度、及び、表面乾燥性が得られる点から、５００〜５，０００の範囲であることがより好ましい。なお、前記空気乾燥性不飽和樹脂（Ａ）の数平均分子量は、ゲル・パーミエーション・クロマトグラフィー（ＧＰＣ）法により、下記の条件で測定した値を示す。 The number average molecular weight of the air drying unsaturated resin (A) is more preferably in the range of 500 to 5,000 from the viewpoint of obtaining good mechanical strength and surface drying properties. In addition, the number average molecular weight of the said air-drying unsaturated resin (A) shows the value measured on condition of the following by the gel permeation chromatography (GPC) method.
測定装置：高速ＧＰＣ装置（東ソー株式会社製「ＨＬＣ−８２２０ＧＰＣ」）
カラム：東ソー株式会社製の下記のカラムを直列に接続して使用した。
「ＴＳＫｇｅｌ Ｇ５０００」（７．８ｍｍＩ．Ｄ．×３０ｃｍ）×１本
「ＴＳＫｇｅｌ Ｇ４０００」（７．８ｍｍＩ．Ｄ．×３０ｃｍ）×１本
「ＴＳＫｇｅｌ Ｇ３０００」（７．８ｍｍＩ．Ｄ．×３０ｃｍ）×１本
「ＴＳＫｇｅｌ Ｇ２０００」（７．８ｍｍＩ．Ｄ．×３０ｃｍ）×１本
検出器：ＲＩ（示差屈折計）
カラム温度：４０℃
溶離液：テトラヒドロフラン（ＴＨＦ）
流速：１．０ｍＬ／分
注入量：１００μＬ（試料濃度０．４質量％のテトラヒドロフラン溶液）
標準試料：下記の標準ポリスチレンを用いて検量線を作成した。Measuring device: High-speed GPC device (“HLC-8220GPC” manufactured by Tosoh Corporation)
Column: The following columns manufactured by Tosoh Corporation were connected in series.
"TSKgel G5000" (7.8 mm ID x 30 cm) x 1 "TSKgel G4000" (7.8 mm ID x 30 cm) x 1 "TSKgel G3000" (7.8 mm ID x 30 cm) x 1 “TSKgel G2000” (7.8 mm ID × 30 cm) × 1 detector: RI (differential refractometer)
Column temperature: 40 ° C
Eluent: Tetrahydrofuran (THF)
Flow rate: 1.0 mL / min Injection amount: 100 μL (tetrahydrofuran solution with a sample concentration of 0.4 mass%)
Standard sample: A calibration curve was prepared using the following standard polystyrene.
（標準ポリスチレン）
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ａ−５００」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ａ−１０００」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ａ−２５００」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ａ−５０００」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−１」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−２」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−４」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−１０」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−２０」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−４０」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−８０」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−１２８」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−２８８」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−５５０」(Standard polystyrene)
"TSKgel standard polystyrene A-500" manufactured by Tosoh Corporation
"TSKgel standard polystyrene A-1000" manufactured by Tosoh Corporation
"TSKgel standard polystyrene A-2500" manufactured by Tosoh Corporation
"TSKgel standard polystyrene A-5000" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-1" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-2" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-4" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-10" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-20" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-40" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-80" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-128" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-288" manufactured by Tosoh Corporation
"TSKgel standard polystyrene F-550" manufactured by Tosoh Corporation
前記空気乾燥性不飽和樹脂（Ａ）の含有量としては、表面乾燥性及び湿潤面接着性を高いレベルで維持できる点から、ラジカル重合性樹脂組成物中１０〜６０質量％の範囲であることが好ましく、１５〜５０質量％の範囲であることがより好ましい。 The content of the air-drying unsaturated resin (A) is in the range of 10 to 60% by mass in the radical polymerizable resin composition from the viewpoint that the surface drying property and wet surface adhesiveness can be maintained at a high level. Is preferable, and it is more preferable that it is the range of 15-50 mass%.
前記ラジカル重合性単量体（Ｂ）としては、例えば、メチル（メタ）アクリレート、エチル（メタ）アクリレート、ｎ−ブチル（メタ）アクリレート、イソブチル（メタ）アクリレート、ｔ−ブチル（メタ）アクリレート、ヘキシル（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−オクチル（メタ）アクリレート、デシル（メタ）アクリレート、２−ヒドロキシエチル（メタ）アクリレート、２−ヒドロキシプロピル（メタ）アクリレート、β−エトキシエチル（メタ）アクリレート、２−シアノエチル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、ジエチルアミノエチル（メタ）アクリレート、ラウリル（メタ）アクリレート、ステアリル（メタ）アクリレート、ポリカプロラクトン（メタ）アクリレート、ジエチレングリコールモノメチルエーテルモノ（メタ）アクリレート、ジプロピレングリコールモノメチルエーテルモノ（メタ）アクリレート、２−エチルヘキシルカルビトール（メタ）アクリレート、トリス（２−ヒドロキシエチル）イソシアヌル（メタ）アクリレート等の（メタ）アクリル単量体；ジシクロペンテニルオキシエチル（メタ）アクリレート、ジシクロペンテニル（メタ）アクリレート、フェノキシエチル（メタ）アクリレート等の沸点が１００℃以上の（メタ）アクリル単量体等を用いることできる。これらの単量体は単独で用いても２種以上を併用してもよい。 Examples of the radical polymerizable monomer (B) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, and hexyl. (Meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, decyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, β-ethoxyethyl ( (Meth) acrylate, 2-cyanoethyl (meth) acrylate, cyclohexyl (meth) acrylate, diethylaminoethyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, polycaprolactone (meth) acrylate (Meth) acrylic such as dirate glycol monomethyl ether mono (meth) acrylate, dipropylene glycol monomethyl ether mono (meth) acrylate, 2-ethylhexyl carbitol (meth) acrylate, tris (2-hydroxyethyl) isocyanuric (meth) acrylate Monomer: (Meth) acrylic monomers having a boiling point of 100 ° C. or higher, such as dicyclopentenyloxyethyl (meth) acrylate, dicyclopentenyl (meth) acrylate, phenoxyethyl (meth) acrylate, and the like can be used. These monomers may be used alone or in combination of two or more.
ラジカル重合性単量体（Ｂ）の含有量としては、塗膜の良好な機械的強度が得られる点で、ラジカル重合性樹脂組成物中１０〜８０質量％の範囲であることが好ましく、３０〜７０質量％の範囲であることがより好ましい。 The content of the radically polymerizable monomer (B) is preferably in the range of 10 to 80% by mass in the radically polymerizable resin composition in terms of obtaining good mechanical strength of the coating film. More preferably, it is in the range of -70 mass%.
前記シクロデキストリン及び／又はその誘導体（Ｃ）としては、例えば、シクロデキストリン；アルキル化シクロデキストリン、アセチル化シクロデキストリン、ヒドロキシアルキル化シクロデキストリン等のシクロデキストリンのグルコース単位の水酸基の水素原子を他の官能基で置換したものなどを用いることができる。また、シクロデキストリン及びシクロデキストリン誘導体におけるシクロデキストリン骨格としては、６個のグルコース単位からなるα−シクロデキストリン、７個のグルコース単位からなるβ−シクロデキストリン、８個のグルコース単位からなるγ−シクロデキストリンのいずれも用いることができる。これらの化合物は単独で用いても２種以上を併用してもよい。これらの中でも、前記（Ａ）及び（Ｂ）成分との相溶性をより一層向上できる点から、シクロデキストリン誘導体を用いることが好ましく、アルキル化シクロデキストリンを用いることがより好ましい。 Examples of the cyclodextrin and / or its derivative (C) include, for example, cyclodextrin; the hydrogen atom of the hydroxyl group of the glucose unit of cyclodextrin such as alkylated cyclodextrin, acetylated cyclodextrin, and hydroxyalkylated cyclodextrin. Those substituted with a group can be used. The cyclodextrin skeleton in cyclodextrin and cyclodextrin derivatives includes α-cyclodextrin consisting of 6 glucose units, β-cyclodextrin consisting of 7 glucose units, and γ-cyclodextrin consisting of 8 glucose units. Any of these can be used. These compounds may be used alone or in combination of two or more. Among these, it is preferable to use a cyclodextrin derivative, and it is more preferable to use an alkylated cyclodextrin from the point which can further improve compatibility with the said (A) and (B) component.
前記シクロデキストリン誘導体における他の官能基の置換度としては、前記（Ａ）及び（Ｂ）成分との相溶性の点から、０．３〜１４個／グルコースの範囲であることが好ましく、０．５〜８個／グルコースの範囲であることがより好ましい。 The degree of substitution of other functional groups in the cyclodextrin derivative is preferably in the range of 0.3 to 14 / glucose from the viewpoint of compatibility with the components (A) and (B). A range of 5 to 8 / glucose is more preferable.
前記アルキル化シクロデキストリンとしては、例えば、メチル−α−シクロデキストリン、メチル−β−シクロデキストリン、メチル−γ−シクロデキストリン等を用いることができる。これらの化合物は単独で用いても２種以上を併用してもよい。 Examples of the alkylated cyclodextrin include methyl-α-cyclodextrin, methyl-β-cyclodextrin, and methyl-γ-cyclodextrin. These compounds may be used alone or in combination of two or more.
前記アセチル化シクロデキストリンとしては、例えば、モノアセチル−α−シクロデキストリン、モノアセチル−β−シクロデキストリン、モノアセチル−γ−シクロデキストリン等を用いることができる。これらの化合物は単独で用いても２種以上を併用してもよい。 Examples of the acetylated cyclodextrin include monoacetyl-α-cyclodextrin, monoacetyl-β-cyclodextrin, and monoacetyl-γ-cyclodextrin. These compounds may be used alone or in combination of two or more.
前記ヒドロキシアルキル化シクロデキストリンとしては、例えば、ヒドロキシプロピル−α−シクロデキストリン、ヒドロキシプロピル−β−シクロデキストリン、ヒドロキシプロピル−γ−シクロデキストリン等を用いることができる。これらの化合物は単独で用いても２種以上を併用してもよい。 Examples of the hydroxyalkylated cyclodextrin include hydroxypropyl-α-cyclodextrin, hydroxypropyl-β-cyclodextrin, and hydroxypropyl-γ-cyclodextrin. These compounds may be used alone or in combination of two or more.
前記シクロデキストリン及び／又はその誘導体（Ｃ）の含有量としては、良好な湿潤面接着性が得られる点から、ラジカル重合性樹脂組成物中０．１〜２０質量％の範囲であることが好ましく、０．３〜１０質量％の範囲であることがより好ましい。 The content of the cyclodextrin and / or its derivative (C) is preferably in the range of 0.1 to 20% by mass in the radical polymerizable resin composition from the viewpoint of obtaining good wet surface adhesion. The range of 0.3 to 10% by mass is more preferable.
本発明のラジカル重合性樹脂組成物は、前記空気乾燥性不飽和樹脂（Ａ）、前記ラジカル重合性単量体（Ｂ）、並びに、前記シクロデキストリン及び／又はその誘導体（Ｃ）を必須成分として含有するが、必要に応じてその他の添加剤を含有してもよい。 The radical polymerizable resin composition of the present invention comprises the air-drying unsaturated resin (A), the radical polymerizable monomer (B), and the cyclodextrin and / or derivative (C) as essential components. Although it contains, you may contain other additives as needed.
前記その他の添加剤としては、例えば、ラジカル重合性樹脂、硬化剤、硬化促進剤、重合禁止剤、顔料、チキソ性付与剤、酸化防止剤、溶剤、充填剤、補強材、骨材、難燃剤、石油ワックス等を１種以上用いることができる。 Examples of the other additives include radical polymerizable resins, curing agents, curing accelerators, polymerization inhibitors, pigments, thixotropic agents, antioxidants, solvents, fillers, reinforcing materials, aggregates, and flame retardants. One or more petroleum waxes can be used.
前記ラジカル重合性樹脂は、塗膜の機械的強度の調整する目的で用いることができ、例えば、不飽和ポリエステル、ポリエステル（メタ）アクリレート、エポキシ（メタ）アクリレート、ウレタン（メタ）アクリレート等を用いることができる。前記ラジカル重合性樹脂を用いる場合の使用量としては、ラジカル重合性樹脂組成物中０．１〜３０質量％の範囲であることが好ましい。 The radical polymerizable resin can be used for the purpose of adjusting the mechanical strength of the coating film. For example, unsaturated polyester, polyester (meth) acrylate, epoxy (meth) acrylate, urethane (meth) acrylate, or the like is used. Can do. The amount of the radical polymerizable resin used is preferably in the range of 0.1 to 30% by mass in the radical polymerizable resin composition.
前記硬化剤としては、常温での表面乾燥性の点から有機過酸化物を用いることが好ましく、例えば、ジアシルパーオキサイド化合物、パーオキシエステル化合物、ハイドロパーオキサイド化合物、ジアルキルパーオキサイド化合物、ケトンパーオキサイド化合物、パーオキシケタール化合物、アルキルパーエステル化合物、パーカーボネート化合物等を用いることができる。これらの硬化剤は単独で用いても２種以上を併用してもよい。前記硬化剤を用いる場合の使用量としては、ラジカル重合性樹脂組成物中０．０１〜１０質量％の範囲であることが好ましい。 As the curing agent, an organic peroxide is preferably used from the viewpoint of surface dryness at room temperature. For example, a diacyl peroxide compound, a peroxy ester compound, a hydroperoxide compound, a dialkyl peroxide compound, a ketone peroxide. A compound, a peroxyketal compound, an alkyl perester compound, a carbonate compound, or the like can be used. These curing agents may be used alone or in combination of two or more. When using the said hardening | curing agent, it is preferable that it is the range of 0.01-10 mass% in a radically polymerizable resin composition.
前記硬化促進剤は、前記硬化剤の有機過酸化物をレドックス反応によって分解し、活性ラジカルの発生を容易にする作用のある物質であり、例えば、ナフテン酸コバルト、オクチル酸コバルト等のコバルト有機酸塩、オクチル酸亜鉛、オクチル酸バナジウム、ナフテン酸銅、ナフテン酸バリウム等の金属石鹸、バナジウムアセチルアセテート、コバルトアセチルアセテート、鉄アセチルアセトネート等の金属キレート；アニリン、Ｎ，Ｎ−ジメチルアニリン、Ｎ，Ｎ−ジエチルアニリン、ｐ−トルイジン、Ｎ，Ｎ−ジメチル−ｐ−トルイジン、Ｎ，Ｎ−ジメチル−ｐ−トルイジンのエチレンオキサイド付加物、Ｎ，Ｎ−ビス（２-ヒドロキシエチル）−ｐ−トルイジン、４−（Ｎ，Ｎ−ジメチルアミノ）ベンズアルデヒド、４−［Ｎ，Ｎ−ビス（２-ヒドロキシエチル）アミノ］ベンズアルデヒド、４−（Ｎ−メチル−Ｎ−ヒドロキシエチルアミノ）ベンズアルデヒド、Ｎ，Ｎ−ビス（２−ヒドロキシプロピル）−ｐ−トルイジン、Ｎ−エチル−ｍ−トルイジン、トリエタノールアミン、ｍ−トルイジン、ジエチレントリアミン、ピリジン、フェニリモルホリン、ピペリジン、Ｎ，Ｎ−ビス（ヒドロキシエチル）アニリン、ジエタノールアニリン等のＮ，Ｎ−置換アニリン；Ｎ，Ｎ−置換−ｐ−トルイジン、４−（Ｎ，Ｎ−置換アミノ）ベンズアルデヒド等のアミン化合物などを用いることができる。これらの硬化促進剤は単独で用いても２種以上を併用してもよい。前記硬化促進剤を用いる場合の使用量としては、ラジカル重合性樹脂組成物中０．０１〜５質量％の範囲であることが好ましい。 The curing accelerator is a substance having an action of decomposing an organic peroxide of the curing agent by a redox reaction and facilitating generation of active radicals. For example, a cobalt organic acid such as cobalt naphthenate and cobalt octylate is used. Metal soaps such as salts, zinc octylate, vanadium octylate, copper naphthenate, barium naphthenate, metal chelates such as vanadium acetyl acetate, cobalt acetyl acetate, iron acetylacetonate; aniline, N, N-dimethylaniline, N, N-diethylaniline, p-toluidine, N, N-dimethyl-p-toluidine, ethylene oxide adduct of N, N-dimethyl-p-toluidine, N, N-bis (2-hydroxyethyl) -p-toluidine, 4- (N, N-dimethylamino) benzaldehyde, 4- [N, N-bis (2-hydroxyethyl) amino] benzaldehyde, 4- (N-methyl-N-hydroxyethylamino) benzaldehyde, N, N-bis (2-hydroxypropyl) -p-toluidine, N-ethyl-m-toluidine, tri N, N-substituted anilines such as ethanolamine, m-toluidine, diethylenetriamine, pyridine, phenylmorpholine, piperidine, N, N-bis (hydroxyethyl) aniline, diethanolaniline; N, N-substituted-p-toluidine, 4 An amine compound such as-(N, N-substituted amino) benzaldehyde can be used. These curing accelerators may be used alone or in combination of two or more. When using the said hardening accelerator, it is preferable that it is the range of 0.01-5 mass% in a radically polymerizable resin composition as a usage-amount.
前記石油ワックスとしては、酸素による硬化阻害を防止するものであり、例えば、融点が３０〜８０℃の石油ワックスを用いることが好ましく、具体的には、パラフィンワックス、マイクロクリスタリンワックス、ペトロラクタム等を用いることができる。これらの石油ワックスは単独で用いても２種以上を併用してもよい。前記石油ワックスを用いる場合の使用量としては、ラジカル重合性樹脂組成物中０．０１〜５質量％の範囲であることが好ましい。 The petroleum wax is one that prevents curing inhibition by oxygen. For example, petroleum wax having a melting point of 30 to 80 ° C. is preferably used. Specifically, paraffin wax, microcrystalline wax, petrolactam, and the like are used. Can be used. These petroleum waxes may be used alone or in combination of two or more. When the petroleum wax is used, the amount used is preferably in the range of 0.01 to 5% by mass in the radical polymerizable resin composition.
本発明のラジカル重合性樹脂組成物の粘度としては、例えば、１０〜１００ｍＰａ・ｓの範囲であることが好ましい。また、前記空気乾燥性不飽和樹脂（Ａ）として、ジシクロペンタジエニル基を有する不飽和ポリエステルを用いた場合には、一層の低粘度化が達成でき、例えば、１〜５０ｍＰａ・ｓの範囲である。なお、前記ラジカル重合性樹脂組成物の粘度は、ＪＩＳＫ６９０１：２００８の「５．５．１ブルックフィールド形粘度計法を用いる場合」に準拠して測定した値を示す。 As a viscosity of the radically polymerizable resin composition of this invention, it is preferable that it is the range of 10-100 mPa * s, for example. Further, when an unsaturated polyester having a dicyclopentadienyl group is used as the air-drying unsaturated resin (A), a further reduction in viscosity can be achieved, for example, in the range of 1 to 50 mPa · s. It is. The viscosity of the radical polymerizable resin composition is a value measured according to JIS K 6901: 2008 “5.5.1 When using Brookfield viscometer method”.
以上、本発明のラジカル重合性樹脂組成物は、表面乾燥性及び湿潤面接着性に優れるものである。従って、本発明のラジカル重合性樹脂組成物は、工場、倉庫、クリーンルーム等の床材；舗装材、防水材、塗料、プライマー、壁面コーティング材、道路マーキング材、注入材、シール材、注型品、積層品、接着剤、ライニング材、波平板等の土木建築材料の製造に好適に使用することができ、土木建築用プライマーとして特に好適に使用することができる。 As described above, the radical polymerizable resin composition of the present invention is excellent in surface drying property and wet surface adhesiveness. Therefore, the radically polymerizable resin composition of the present invention is used for flooring materials such as factories, warehouses, and clean rooms; paving materials, waterproofing materials, paints, primers, wall coating materials, road marking materials, injection materials, sealing materials, and cast products. It can be suitably used for the production of civil engineering and building materials such as laminates, adhesives, lining materials and corrugated plates, and can be particularly suitably used as a primer for civil engineering and construction.
以下、実施例を用いて、本発明をより詳細に説明する。 Hereinafter, the present invention will be described in more detail with reference to examples.
［合成例１］ジシクロペンタジエニル基を有する不飽和ポリエステル（Ａ−１）の合成
温度計、攪拌機、不活性ガス導入口、空気導入口及び還流冷却器を備えた四ツ口フラスコに、水を２７０質量部、ジシクロペンタジエンを１，９８０質量部、ハイドロキノンを０．５質量部、エチレングリコールを４５０質量部仕込み、窒素気流下８０℃で４時間反応させた。酸価が２１０ｍｇＫＯＨ／ｇとなった時点で無水マレイン酸を１，３７０質量部仕込み、２００℃で６時間反応させ、酸価が８ｍｇＫＯＨ／ｇのジシクロペンタジエニル基を有する不飽和ポリエステル（Ａ−１）（以下、「ＤＣＰＤ−ＵＰＥ（Ａ−１）」と略記する。）を得た。[Synthesis Example 1] Synthesis of unsaturated polyester (A-1) having dicyclopentadienyl group In a four-necked flask equipped with a thermometer, stirrer, inert gas inlet, air inlet and reflux condenser, 270 parts by mass of water, 1,980 parts by mass of dicyclopentadiene, 0.5 parts by mass of hydroquinone, and 450 parts by mass of ethylene glycol were charged and reacted at 80 ° C. for 4 hours in a nitrogen stream. When the acid value reached 210 mgKOH / g, 1,370 parts by mass of maleic anhydride was added and reacted at 200 ° C. for 6 hours to obtain an unsaturated polyester having a dicyclopentadienyl group having an acid value of 8 mgKOH / g (A -1) (hereinafter abbreviated as “DCPD-UPE (A-1)”).
［合成例２］エポキシメタクリレート（１）の合成
温度計、攪拌機、不活性ガス導入口、空気導入口及び還流冷却器を備えた四ツ口フラスコに、エポキシ化合物（ＤＩＣ株式会社製「エピクロン８５０」）を１，８５０質量部、メタクリル酸を８６０質量部、ハイドロキノンを１．３６質量部、トリエチルアミンを１０．８質量部を仕込み、１２０℃まで昇温させ、同次官で１０時間反応させ、ラジカル重合性樹脂（１９として酸価が３．５ｍｇＫＯＨ／ｇのエポキシメタクリレート（１）を得た。Synthesis Example 2 Synthesis of Epoxy Methacrylate (1) An epoxy compound (“Epiclon 850” manufactured by DIC Corporation) was placed in a four-necked flask equipped with a thermometer, a stirrer, an inert gas inlet, an air inlet, and a reflux condenser. ) 1,850 parts by weight, methacrylic acid 860 parts by weight, hydroquinone 1.36 parts by weight, triethylamine 10.8 parts by weight, heated to 120 ° C., reacted for 10 hours by the same officer, radical polymerization (Epoxy methacrylate (1) having an acid value of 3.5 mgKOH / g as 19 was obtained.
［合成例３］ウレタンメタクリレート（２）の合成
温度計、攪拌機、不活性ガス導入口、空気導入口及び還流冷却器を備えた四ツ口フラスコに、数平均分子量１，２００のポリブタジエンジオールを５００質量部、トリレンジイソシアネートを１１４質量部仕込み、窒素気流下８０℃で２時間反応させた。イソシアネート基当量が５００とほぼ理論値となったのを確認して、５０℃まで冷却した。次いで、空気気流下でハイドロキノン０．０７質量部、２−ヒドロキシエチルメタクリレートを８９質量部を加え、９０℃で１０時間反応させた。イソシアネート％が０．１％以下となった時点でターシャリーブチルカテコールを０．０７質量部加え、ラジカル重合性樹脂（２）として数平均分子量；２，０６７のウレタンメタクリレート（２）を得た。Synthesis Example 3 Synthesis of Urethane Methacrylate (2) A polybutadiene diol having a number average molecular weight of 1,200 was added to a four-necked flask equipped with a thermometer, a stirrer, an inert gas inlet, an air inlet, and a reflux condenser. Part by mass and 114 parts by mass of tolylene diisocyanate were charged and reacted at 80 ° C. for 2 hours under a nitrogen stream. After confirming that the isocyanate group equivalent was almost the theoretical value of 500, it was cooled to 50 ° C. Next, 0.07 parts by mass of hydroquinone and 89 parts by mass of 2-hydroxyethyl methacrylate were added under an air stream and reacted at 90 ° C. for 10 hours. When the isocyanate% became 0.1% or less, 0.07 part by mass of tertiary butyl catechol was added to obtain urethane methacrylate (2) having a number average molecular weight of 2,067 as the radical polymerizable resin (2).
［合成例４］ウレタンメタクリレート（３）の合成
温度計、攪拌機、不活性ガス導入口、空気導入口及び還流冷却器を備えた四つ口フラスコに、数平均分子量１，０００のポリカーボネートジオールを５００質量部、トリレンジイソシアネートを１７２質量部仕込み、窒素気流下８０℃で２時間反応させた。イソシアネート基当量が６００とほぼ理論値となったのを確認して、５０℃まで冷却した。次いで、空気気流下でハイドロキノン０．０７質量部、２−ヒドロキシエチルメタクリレートを１３５質量部を加え、９０℃で４時間反応させた。イソシアネート％が０．１％以下となった時点でターシャリーブチルカテコールを０．０７質量部加え、ラジカル重合性樹脂（３）として数平均分子量；１，５８２のウレタンメタクリレート（３）を得た。Synthesis Example 4 Synthesis of Urethane Methacrylate (3) A polycarbonate diol having a number average molecular weight of 1,000 was added to a four-necked flask equipped with a thermometer, a stirrer, an inert gas inlet, an air inlet and a reflux condenser. Part by mass and 172 parts by mass of tolylene diisocyanate were charged and reacted at 80 ° C. for 2 hours under a nitrogen stream. It was confirmed that the isocyanate group equivalent was 600, which was almost the theoretical value, and then cooled to 50 ° C. Next, 0.07 parts by mass of hydroquinone and 135 parts by mass of 2-hydroxyethyl methacrylate were added under an air stream and reacted at 90 ° C. for 4 hours. When the isocyanate% became 0.1% or less, 0.07 part by mass of tertiary butylcatechol was added to obtain urethane methacrylate (3) having a number average molecular weight of 1,582 as the radical polymerizable resin (3).
［実施例１］ラジカル重合性樹脂組成物の調製
合成例１で得られたＤＣＰＤ−ＵＰＥ（Ａ−１）を３０質量部、合成例２で得られたエポキシメタクリレート（１）を５質量部、メチルメタクリレートを２９質量部、ジシクロペンテニルオキシエチルメタクリレートを３６質量部、純正化学株式会社製「メチル−β−シクロデキストリン」を４質量部混合、撹拌してラジカル重合性樹脂組成物を得た。[Example 1] Preparation of radical polymerizable resin composition 30 parts by mass of DCPD-UPE (A-1) obtained in Synthesis Example 1 and 5 parts by mass of epoxy methacrylate (1) obtained in Synthesis Example 2; 29 parts by mass of methyl methacrylate, 36 parts by mass of dicyclopentenyloxyethyl methacrylate, and 4 parts by mass of “methyl-β-cyclodextrin” manufactured by Junsei Chemical Co., Ltd. were mixed and stirred to obtain a radical polymerizable resin composition.
［実施例２〜５、比較例１〜４］
用いる空気乾燥性不飽和樹脂（Ａ）の量、ラジカル重合性樹脂の種類及び／又は量、ラジカル重合性単量体の量、並びに、シクロデキストリン（Ｃ）の量を表１〜２に示す通りに変更した以外は、実施例１と同様にしてラジカル重合性樹脂組成物を得た。[Examples 2 to 5, Comparative Examples 1 to 4]
The amount of the air-drying unsaturated resin (A) used, the type and / or amount of the radical polymerizable resin, the amount of the radical polymerizable monomer, and the amount of the cyclodextrin (C) are shown in Tables 1-2. A radical polymerizable resin composition was obtained in the same manner as in Example 1 except for changing to.
［表面乾燥性の評価方法］
実施例及び比較例で得られたラジカル重合性樹脂組成物５０質量部に、８質量％オクチル酸コバルトを０．２５質量部、トルイジン化合物イソプロパノール溶液（ディーエイチ・マテリアル株式会社製「ＲＰ−１９１」）を０．５質量部、４０質量％ベンゾイルパーオキサイド溶液を１質量部添加・混合し試験片とした。この試験片をスレート板上に１ｋｇ／ｍ２の量で刷毛にて塗り広げた。これを基点とし、指触にてタックフリーとなる時間（分）を測定した。[Evaluation method of surface drying]
To 50 parts by mass of the radical polymerizable resin compositions obtained in Examples and Comparative Examples, 0.25 part by mass of 8% by mass cobalt octylate, toluidine compound isopropanol solution (“RP-191” manufactured by DH Material Co., Ltd.) 0.5 parts by mass and 1 part by mass of a 40% by mass benzoyl peroxide solution were added and mixed to obtain a test piece. This test piece was spread on a slate plate with a brush in an amount of 1 kg / m 2 . Using this as a base point, the time (minutes) for tack-free by finger touch was measured.
［湿潤面接着性の評価方法］
前記［表面乾燥性の評価方法］の評価において得られた試験片を使用した。１日水浸し、その後取出して水滴を拭き取った舗装板の上に、前記試験片を０．２ｋｇ／ｍ２の量で刷毛にて塗り広げた。その塗膜を１日養生した後、建研式引張試験機（サンコーテクノ株式会社製「テクノスターＲＴ−３０００ＬＤ」）を使用して、垂直に引張り、剥離強度を測定した。[Method for evaluating wet surface adhesion]
The test piece obtained in the evaluation of [Surface drying property evaluation method] was used. The test piece was spread with a brush in an amount of 0.2 kg / m 2 on a paving board which had been immersed in water for one day and then taken out and wiped off water droplets. After the coating film was cured for one day, it was pulled vertically using a Kenken tensile tester (“Technostar RT-3000LD” manufactured by Sanko Techno Co., Ltd.), and the peel strength was measured.
［粘度の測定方法］
実施例及び比較例で得られたラジカル重合性樹脂組成物を、ＪＩＳＫ６９０１：２００８の「５．５．１ブルックフィールド形粘度計法を用いる場合」に準拠して、表７のタイプｉ、ＢＭ粘度計により粘度を測定した。[Measurement method of viscosity]
The radically polymerizable resin compositions obtained in Examples and Comparative Examples were prepared in accordance with JISK6901: 2008 “5.5.1 When using Brookfield viscometer method”. The viscosity was measured with a meter.
本発明のラジカル重合性樹脂組成物である実施例１〜５は、表面乾燥性及び湿潤面接着性に優れ、かつ低粘度であることが分かった。 It turned out that Examples 1-5 which are radically polymerizable resin compositions of this invention are excellent in surface drying property and wet surface adhesiveness, and are low-viscosity.
一方、比較例１〜２は空気乾燥性不飽和樹脂（Ａ）を含有しない態様であるが、表面乾燥性が不良であった。また、粘度も高い値を示した。 On the other hand, although Comparative Examples 1-2 is an aspect which does not contain air drying unsaturated resin (A), the surface drying property was unsatisfactory. Also, the viscosity showed a high value.
比較例３〜４はシクロデキストリン及び／又はその誘導体（Ｃ）を含有しない態様であるが、湿潤面接着性が十分でなかった。 Although Comparative Examples 3-4 are the aspects which do not contain cyclodextrin and / or its derivative (C), the wet surface adhesiveness was not enough.
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| WO2010146912A1 (en) * | 2009-06-18 | 2010-12-23 | Dic株式会社 | Air-drying polyester (meth)acrylate resin composition, structure and method for providing same |
| JP2014118451A (en) * | 2012-12-14 | 2014-06-30 | Dic Corp | Radical polymerizable resin composition, primer and floor slab waterproofing structure |
| WO2015064191A1 (en) * | 2013-10-30 | 2015-05-07 | Dic株式会社 | Concrete repair material |
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