JP2005098022A - Coated composition for civil engineering/construction material, paving material, and pavement - Google Patents
Coated composition for civil engineering/construction material, paving material, and pavement Download PDFInfo
- Publication number
- JP2005098022A JP2005098022A JP2003335178A JP2003335178A JP2005098022A JP 2005098022 A JP2005098022 A JP 2005098022A JP 2003335178 A JP2003335178 A JP 2003335178A JP 2003335178 A JP2003335178 A JP 2003335178A JP 2005098022 A JP2005098022 A JP 2005098022A
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- JP
- Japan
- Prior art keywords
- resin
- acid
- civil engineering
- pavement
- molecular weight
- 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.)
- Granted
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- 239000000463 material Substances 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title abstract description 7
- 239000004035 construction material Substances 0.000 title abstract description 3
- 229920005989 resin Polymers 0.000 claims abstract description 42
- 239000011347 resin Substances 0.000 claims abstract description 42
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 15
- 229920006337 unsaturated polyester resin Polymers 0.000 claims abstract description 12
- 238000007605 air drying Methods 0.000 claims abstract description 11
- 239000000178 monomer Substances 0.000 claims abstract description 10
- 229920005992 thermoplastic resin Polymers 0.000 claims abstract description 10
- HNPDNOZNULJJDL-UHFFFAOYSA-N ethyl n-ethenylcarbamate Chemical compound CCOC(=O)NC=C HNPDNOZNULJJDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 8
- 239000008199 coating composition Substances 0.000 claims description 18
- 239000004566 building material Substances 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 2
- 229920001169 thermoplastic Polymers 0.000 claims description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims 1
- 239000004416 thermosoftening plastic Substances 0.000 claims 1
- 239000002689 soil Substances 0.000 abstract description 3
- 125000005397 methacrylic acid ester group Chemical group 0.000 abstract 1
- -1 acrylic compound Chemical class 0.000 description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 150000005846 sugar alcohols Polymers 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- 239000003822 epoxy resin Substances 0.000 description 11
- 229920000647 polyepoxide Polymers 0.000 description 11
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical group C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 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 9
- 150000001875 compounds Chemical class 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 239000004925 Acrylic resin Substances 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
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- 150000003077 polyols Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000004567 concrete Substances 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- MOBNLCPBAMKACS-UHFFFAOYSA-N 2-(1-chloroethyl)oxirane Chemical compound CC(Cl)C1CO1 MOBNLCPBAMKACS-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000010426 asphalt Substances 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 229940049920 malate Drugs 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920006305 unsaturated polyester Polymers 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 2
- KFIRODWJCYBBHY-UHFFFAOYSA-N 3-nitrophthalic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1C(O)=O KFIRODWJCYBBHY-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-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
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 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 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000011187 glycerol Nutrition 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
- 239000003999 initiator Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
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- 239000005056 polyisocyanate Substances 0.000 description 2
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- 230000000379 polymerizing effect Effects 0.000 description 2
- 150000007519 polyprotic acids Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
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- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
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- ZQHJVIHCDHJVII-OWOJBTEDSA-N (e)-2-chlorobut-2-enedioic acid Chemical compound OC(=O)\C=C(\Cl)C(O)=O ZQHJVIHCDHJVII-OWOJBTEDSA-N 0.000 description 1
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- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
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- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-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
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- 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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- 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
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
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- BQKZEKVKJUIRGH-UHFFFAOYSA-N 2-prop-2-enoxypropan-1-ol Chemical compound OCC(C)OCC=C BQKZEKVKJUIRGH-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
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- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
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- 239000004342 Benzoyl peroxide Substances 0.000 description 1
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- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Road Paving Structures (AREA)
- Paints Or Removers (AREA)
Abstract
Description
本発明は、特に硬化時の表面硬化性及び耐汚れ性に優れた土木建築材用被覆構造体、特に舗装体を得ることのできる土木建築材用被覆組成物を提供するものである。 The present invention provides a coating structure for civil engineering and building materials, particularly a civil engineering and building material coating composition capable of obtaining a pavement, which is excellent in surface curability and soil resistance during curing.
従来、土木建築材用樹脂としては、エポキシ樹脂、ポリウレタン樹脂などが代表的に用いられているが、これらの樹脂はいずれも高粘度であり、溶剤に溶解した形で利用されている。これら溶剤型土木建築材用樹脂とは別に、不飽和ポリエステル樹脂、ビニルエステル樹脂を用いた土木建築材用樹脂は、併用されているモノマーが溶剤を兼ねており、塗膜は一般の溶剤型土木建築材用樹脂と異なり１００％固化型である。これらの樹脂は一般にラジカル重合によって硬化するが、土木建築材用被覆組成物として用いる場合、空気中の酸素がラジカル重合を阻害し、表面の乾燥性が悪く、汚れの残りやすい被覆材となるという欠点がある。これらを補うためにワックスの添加、あるいは空乾性能を有する樹脂を用いている（例えば特許文献１参照）のが現状である。 Conventionally, epoxy resins, polyurethane resins and the like are typically used as resins for civil engineering and building materials, but these resins have high viscosity and are used in a form dissolved in a solvent. In addition to these solvent-type resins for civil engineering and building materials, in civil engineering and building resin using unsaturated polyester resin and vinyl ester resin, the monomer used in combination also serves as a solvent, and the coating film is a general solvent-type civil engineering Unlike resin for building materials, it is 100% solidified. These resins are generally cured by radical polymerization, but when used as a civil engineering and building material coating composition, oxygen in the air inhibits radical polymerization, resulting in a coating material that has poor surface drying properties and is likely to remain dirty. There are drawbacks. In order to make up for these problems, the present situation is that a resin having a wax addition or air-drying performance is used (see, for example, Patent Document 1).
しかしながら、ワックスの添加は塗膜表面における空気遮断作用のため、空気乾燥性の向上に寄与する反面、硬化後も塗膜表面に存在し、塗膜の二次接着性及び外観などに影響を与えることが多い。また、空乾性能を有する成分のみを用いる場合、未硬化の低分子量成分が残存すると硬化後も汚れやすいという問題がある。
本発明の目的は、表面乾燥性及び耐汚れ性に優れる土木建築材用被覆組成物、特に舗装材を提供することである。 The objective of this invention is providing the coating composition for civil engineering and building materials excellent in surface drying property and stain resistance, especially a paving material.
本発明者らは、これらの課題について鋭意研究の結果、特定の数平均分子量を有する熱可塑性重合体を用いることにより、表面乾燥性及び耐汚れ性が向上することを発見することにより、本発明を完成するに至ったものである。 As a result of diligent research on these problems, the present inventors have found that the use of a thermoplastic polymer having a specific number average molecular weight improves the surface drying property and stain resistance, and thereby the present invention. Has been completed.
即ち、本発明は、（Ａ）ビニルエステル樹脂、ビニルウレタン樹脂及び不飽和ポリエステル樹脂からなる群から選ばれる少なくとも１種の樹脂、（Ｂ）重合性単量体及び（Ｃ）数平均分子量が５，０００〜２００，０００の熱可塑性樹脂を必須成分とする土木建設材用被覆組成物を提供するものである。また本発明は、（Ａ）ビニルエステル樹脂、ビニルウレタン樹脂及び不飽和ポリエステル樹脂からなる群から選ばれる少なくとも１種の樹脂、（Ｂ）重合性単量体、（Ｃ）数平均分子量が５，０００〜２００，０００の熱可塑性樹脂及び骨材を必須成分とする舗装材を提供するものである。さらに本発明は、前記舗装材を舗装面に塗布し、硬化させてなる舗装体を提供するものである。 That is, in the present invention, (A) at least one resin selected from the group consisting of a vinyl ester resin, a vinyl urethane resin and an unsaturated polyester resin, (B) a polymerizable monomer and (C) a number average molecular weight is 5 The present invention provides a coating composition for civil engineering and construction materials comprising a thermoplastic resin of 1,000,000 to 200,000 as an essential component. The present invention also includes (A) at least one resin selected from the group consisting of vinyl ester resins, vinyl urethane resins, and unsaturated polyester resins, (B) a polymerizable monomer, and (C) a number average molecular weight of 5, The present invention provides a paving material comprising 000 to 200,000 thermoplastic resin and aggregate as essential components. Furthermore, this invention provides the pavement formed by apply | coating the said pavement material to a pavement surface, and making it harden | cure.
本発明の土木建築材用被覆組成物及び舗装材は、表面乾燥性及び耐汚れ性に優れるので、舗装材等の土木建築材の用途に有用である。 Since the coating composition for civil engineering and building materials and the paving material of the present invention are excellent in surface drying property and stain resistance, it is useful for applications of civil engineering and building materials such as paving materials.
以下本発明をさらに詳細に説明する。
本発明に使用する樹脂（Ａ）は、ビニルエステル樹脂、ビニルウレタン樹脂及び不飽和ポリエステル樹脂のうち、少なくとも１種の樹脂である。
The present invention is described in further detail below.
The resin (A) used in the present invention is at least one resin among vinyl ester resins, vinyl urethane resins, and unsaturated polyester resins.
樹脂（Ａ）として用いるビニルエステル樹脂としては、例えばエポキシ樹脂と（メタ）アクリル酸との反応によって製造されるエポキシ（メタ）アクリレート樹脂、飽和あるいは不飽和ポリエステル樹脂の末端に（メタ）アクリル化合物を反応させたポリエステル（メタ）アクリレート樹脂、あるいは末端カルボキシル基を有するポリブタジエンとグリシジル（メタ）アクリレートとの反応によって製造されるポリブタジエンタイプのビニルエステル樹脂などが挙げられる。これらのビニルエステル樹脂は、耐食性及び機械的強度が優れるものである。 Examples of the vinyl ester resin used as the resin (A) include an epoxy (meth) acrylate resin produced by a reaction between an epoxy resin and (meth) acrylic acid, and a (meth) acrylic compound at the terminal of a saturated or unsaturated polyester resin. Examples thereof include a polyester (meth) acrylate resin reacted, or a polybutadiene type vinyl ester resin produced by a reaction between polybutadiene having a terminal carboxyl group and glycidyl (meth) acrylate. These vinyl ester resins are excellent in corrosion resistance and mechanical strength.
また樹脂（Ａ）として用いるエポキシ（メタ）アクリレート樹脂は、エポキシ樹脂と（メタ）アクリロリル基を有するカルボン酸とを反応させて得られるものであり、例えばビスフェノールタイプのエポキシ樹脂と（メタ）アクリロリル基を有するカルボン酸とを反応させたもの、ノボラックタイプのエポキシ樹脂と（メタ）アクリロリル基を有するカルボン酸とを反応させたものがある。 The epoxy (meth) acrylate resin used as the resin (A) is obtained by reacting an epoxy resin with a carboxylic acid having a (meth) acrylol group, for example, a bisphenol type epoxy resin and a (meth) acrylol group. And a carboxylic acid having a (meth) acrylolyl group and a novolac type epoxy resin.
前記ビスフェノールタイプのエポキシ樹脂としては、例えばエピクロルヒドリンとビスフェノールＡ若しくはビスフェノールＦとの反応により得られる実質的に１分子中に２個以上のエポキシ基を有するグリシジルエーテル型のエポキシ樹脂、メチルエピクロルヒドリンとビスフェノールＡ若しくはビスフェノールＦとの反応により得られるジメチルグリシジルエーテル型のエポキシ樹脂、あるいはビスフェノールＡのアルキレンオキサイド付加物とエピクロルヒドリン若しくはメチルエピクロルヒドリンとから得られるエポキシ樹脂などが挙げられる。 Examples of the bisphenol type epoxy resin include a glycidyl ether type epoxy resin having substantially two or more epoxy groups in one molecule obtained by reaction of epichlorohydrin and bisphenol A or bisphenol F, methyl epichlorohydrin and bisphenol A, for example. Or the dimethyl glycidyl ether type epoxy resin obtained by reaction with bisphenol F, the epoxy resin obtained from the alkylene oxide adduct of bisphenol A, and epichlorohydrin or methyl epichlorohydrin, etc. are mentioned.
また前記ノボラックタイプのエポキシ樹脂としては、例えばノボラック型フェノール樹脂又はノボラック型クレゾール樹脂とエピクロルヒドリン又はメチルエピクロルヒドリンとの反応により得られるエポキシ樹脂などが挙げられる。 Examples of the novolak type epoxy resin include an epoxy resin obtained by a reaction of a novolak type phenol resin or a novolac type cresol resin with epichlorohydrin or methyl epichlorohydrin.
また、前記の不飽和一塩基酸としては、例えばアクリル酸、メタクリル酸、桂皮酸、クロトン酸、モノメチルマレート、モノブテンマレート、ソルビン酸またはモノ（２−エチルヘキシル）マレート等が挙げられ、これらを単独又は２種以上を併用して用いられる。 Examples of the unsaturated monobasic acid include acrylic acid, methacrylic acid, cinnamic acid, crotonic acid, monomethyl malate, monobutene malate, sorbic acid, and mono (2-ethylhexyl) malate. Are used alone or in combination of two or more.
さらに樹脂（Ａ）として用いられるポリエステル（メタ）アクリレート樹脂としては、飽和二塩基酸類と多価アルコール類との縮合反応で得られる飽和ポリエステルと（メタ）アクリレート化合物とから得られるものと、α、β−不飽和二塩基酸を含む二塩基酸類と多価アルコール類との縮合で得られる不飽和ポリエステルと（メタ）アクリレート化合物とから得られるものがある。 Furthermore, as the polyester (meth) acrylate resin used as the resin (A), those obtained from a saturated polyester obtained by a condensation reaction of a saturated dibasic acid and a polyhydric alcohol and a (meth) acrylate compound, α, Some are obtained from an unsaturated polyester obtained by condensation of a dibasic acid containing a β-unsaturated dibasic acid with a polyhydric alcohol and a (meth) acrylate compound.
ここでいう飽和二塩基酸類とは、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−ドデカンジカルボン酸、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、またはこれらのジアルキルエステル等を挙げることができる。 Examples of the saturated dibasic acid herein include 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-dodecanedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 2 , 3-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid anhydride, 4,4′-biphenyldicarboxylic acid, or dialkyl esters thereof.
また、多価アルコール類とは、例えば、エチレングリコール、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、トリプロピレングリコール、ポリプロピレングリコール、２−メチル−１，３−プロパンジオール、１，３−ブタンジオール、ネオペンチルグリコール、水素化ビスフェノールＡ、１，４−ブタンジオール、１，６−ヘキサンジオール等を挙げることができる。 Polyhydric alcohols include, for example, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, 2-methyl-1,3-propanediol, 1, Examples include 3-butanediol, neopentyl glycol, hydrogenated bisphenol A, 1,4-butanediol, 1,6-hexanediol, and the like.
不飽和二塩基酸としては、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挙げることができる。 Examples of the unsaturated dibasic acid include maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride and the like.
前記（メタ）アクリル化合物としては、不飽和グリシジル化合物、アクリル酸またはメタクリル酸の如き各種の不飽和一塩基酸、及びそのグリシジルエステル類等である。これらのうち、グリシジル（メタ）アクリレートが好ましい。 Examples of the (meth) acrylic compound include unsaturated glycidyl compounds, various unsaturated monobasic acids such as acrylic acid or methacrylic acid, and glycidyl esters thereof. Of these, glycidyl (meth) acrylate is preferred.
本発明に使用する樹脂（Ａ）として用いるビニルウレタン樹脂は、ポリオール類、イソシアネート類、および水酸基含有（メタ）アクリレート類と原料とするウレタン（メタ）アクリレートのオリゴマーである。 The vinyl urethane resin used as the resin (A) used in the present invention is an oligomer of urethane (meth) acrylate used as a raw material with polyols, isocyanates, and hydroxyl group-containing (meth) acrylates.
かかるウレタン（メタ）アクリレートは、前記ポリオール類と前記イソシアネート類とを反応させて、末端イソシアネート基含有プレポリマーを得、次いでこれに水酸基含有（メタ）アクリレート類を反応させて得ることができる。 Such a urethane (meth) acrylate can be obtained by reacting the polyols with the isocyanate to obtain a terminal isocyanate group-containing prepolymer, and then reacting this with a hydroxyl group-containing (meth) acrylate.
前記ポリオール類としては、ポリエーテルポリオールおよびポリエステルポリオール等が挙げられる。かかるポリエーテルポリオールとしては、例えばポリオキシプロピレンジオール、ポリテトラメチレングリコールエーテル、ポリオキシエチレンジオール等が挙げられ、またポリエステルポリオールとしては、二塩基酸又はその酸無水物と多価アルコール類との重縮合物が挙げられる。 Examples of the polyols include polyether polyols and polyester polyols. Examples of such polyether polyols include polyoxypropylene diol, polytetramethylene glycol ether, and polyoxyethylene diol. Polyester polyols include dibasic acids or their anhydrides and polyhydric alcohols. A condensate is mentioned.
かかる二塩基酸又はその酸無水物としては、例えばフタル酸、無水フタル酸、イソフタル酸、テレフタル酸、ニトロフタル酸、テトラヒドロ無水フタル酸等が挙げられ、これらを単独または２種以上を併用して用いられる。 Examples of such dibasic acids or acid anhydrides thereof include phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, nitrophthalic acid, tetrahydrophthalic anhydride, etc., and these may be used alone or in combination of two or more. It is done.
前記多価アルコール類としては、例えばエチレングリコール、プロピレングリコール、ジエチレングリコール、ジプロピレングリコール、１，３−ブタンジオール、１，４−ブタンジオール、２−メチルプロパンー１，３−ジオール、ネオペンチルグリコール、トリエチレングリコール、テトラエチレングリコール、１，５−ペンタンジオール、１，６−ヘキサンジオール等が挙げられ、これらを単独または２種以上を併用して用いられる。 Examples of the polyhydric alcohols include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, 1,3-butanediol, 1,4-butanediol, 2-methylpropane-1,3-diol, neopentyl glycol, Examples include triethylene glycol, tetraethylene glycol, 1,5-pentanediol, 1,6-hexanediol, and the like. These may be used alone or in combination of two or more.
次に前記イソシアネート類としては、例えば２，４−トリレンジイソシアネートおよびその異性体又は異性体の混合物、ジフェニルメタンジイソシアネート、ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、キシリレンジイソシアネート、水添キシレンジイソシアネート、ジシクロヘキシルメタンジイソシアネート、トリジンジイソシアネート、ナフタリンジイソシアネート、トリフェニルメタントリイソシアネート等のポリイソシアネートが挙げられる。これらのポリイソシアネートのうち、ジイソシアネートが好ましい。これらを単独又は２種以上併用して用いることができる。 Next, examples of the isocyanates include 2,4-tolylene diisocyanate and its isomer or a mixture of isomers, diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, hydrogenated xylene diisocyanate, dicyclohexylmethane diisocyanate, and tolidine. And polyisocyanates such as diisocyanate, naphthalene diisocyanate, and triphenylmethane triisocyanate. Of these polyisocyanates, diisocyanates are preferred. These can be used alone or in combination of two or more.
また前記した水酸基含有（メタ）アクリレート類としては、例えばヒドロキシエチル（メタ）アクリレート、ヒドロキシプロピル（メタ）アクリレート等が挙げられ、これらを単独または２種以上を併用して用いられる。 Examples of the hydroxyl group-containing (meth) acrylates described above include hydroxyethyl (meth) acrylate and hydroxypropyl (meth) acrylate, and these are used alone or in combination of two or more.
次に本発明に使用する樹脂（Ａ）として用いられる不飽和ポリエステル樹脂としては、特に限定されるものではなく、従来一般の土木建築材用被覆組成物に慣用されている公知の不飽和ポリエステル樹脂を用いることができる。公知の不飽和ポリエステル樹脂としては、例えばα，β−エチレン性不飽和二重結合を有するカルボン酸、又はα，β−エチレン性不飽和二重結合を有するカルボン酸とα，β−エチレン性不飽和二重結合を有さない飽和のカルボン酸と多価アルコール類との縮合反応により得られる不飽和ポリエステルが挙げられる。 Next, the unsaturated polyester resin used as the resin (A) used in the present invention is not particularly limited, and is a well-known unsaturated polyester resin conventionally used in general civil engineering coating materials. Can be used. Known unsaturated polyester resins include, for example, carboxylic acids having an α, β-ethylenically unsaturated double bond, or carboxylic acids having an α, β-ethylenically unsaturated double bond and an α, β-ethylenically unsaturated resin. An unsaturated polyester obtained by a condensation reaction between a saturated carboxylic acid having no saturated double bond and a polyhydric alcohol can be mentioned.
かかるα，β―エチレン性不飽和二重結合を有するカルボン酸としては、例えばマレイン酸、無水マレイン酸、フマル酸、イタコン酸、シトラコン酸、クロルマレイン酸が挙げられ、飽和カルボン酸としては、例えばフタル酸、無水フタル酸、イソフタル酸、テレフタル酸、ニトロフタル酸、テトラヒドロ無水フタル酸、シュウ酸、マロン酸、コハク酸、アジピン酸、セバシン酸等が挙げられ、これらを単独または２種以上を併用して用いることができる。 Examples of the carboxylic acid having an α, β-ethylenically unsaturated double bond include maleic acid, maleic anhydride, fumaric acid, itaconic acid, citraconic acid, and chloromaleic acid. Examples of the saturated carboxylic acid include Examples include phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, nitrophthalic acid, tetrahydrophthalic anhydride, oxalic acid, malonic acid, succinic acid, adipic acid, and sebacic acid. These may be used alone or in combination of two or more. Can be used.
多価アルコール類としては、前記した多価アルコールを用いることができる。 As the polyhydric alcohol, the polyhydric alcohol described above can be used.
本発明に使用する空乾性を有する樹脂の空乾性とは、重合体中にある特定の官能基を導入することにより、酸素分子による硬化阻害を受けず、空気中でも速やかに硬化が進行することを言う。この目的で使用され得る樹脂としては、例えば、前記のビニルエステル、不飽和ポリエステル等に必須成分として空乾性基を導入したものが挙げられる。 The air-drying property of the resin having air-drying property used in the present invention means that by introducing a specific functional group in the polymer, curing is not rapidly inhibited by oxygen molecules, but curing proceeds rapidly even in the air. say. Examples of the resin that can be used for this purpose include those obtained by introducing an air-drying group as an essential component into the vinyl ester, unsaturated polyester, and the like.
上記空乾性基の例としては、アリル基をはじめとするアルケニル基、アルケニルエーテル基、およびジシクロペンタジエン基などが挙げられる。 Examples of the air-drying group include alkenyl groups including allylic groups, alkenyl ether groups, and dicyclopentadiene groups.
空乾性基導入方法の例としては、以下の方法を挙げることができる。即ち、1)多価アルコール成分にアリルエーテル基を含有する化合物を併用する。2)多価アルコールと乾性油等の脂肪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をアルコール成分に併用する。3)二塩基酸成分に環状不飽和脂肪族多塩基酸及びその誘導体を含有する化合物を併用する。4)ジシクロペンタジエニル基を含有する化合物を併用する。 Examples of the air-drying group introduction method include the following methods. That is, 1) A compound containing an allyl ether group is used in combination with a polyhydric alcohol component. 2) An alcoholysis compound obtained by a transesterification reaction between a polyhydric alcohol and a fatty oil such as drying oil is used in combination with the alcohol component. 3) A compound containing a cyclic unsaturated aliphatic polybasic acid and a derivative thereof is used in combination with the dibasic acid component. 4) A compound containing a dicyclopentadienyl group is used in combination.
これらの1)〜4)のうち、1)のアリルエーテル基含有化合物としては公知のものがいずれも使用できるが、その代表的なものとしては、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類のアリルエーテル化合物、アリルグリシジルエーテルなどの如きオキシラン環を有するアリルエーテル化合物が挙げられる。 Among these 1) to 4), any known compound can be used as the allyl ether group-containing compound of 1). Typical examples thereof include ethylene glycol monoallyl ether, diethylene glycol monoallyl ether, Ethylene glycol monoallyl ether, polyethylene glycol monoallyl ether, propylene glycol monoallyl ether, 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, glycerin monoallyl ether, glycerin di Rirueteru, pentaerythritol monoallyl ether, pentaerythritol diallyl ether, allyl ether compounds of polyhydric alcohols such as pentaerythritol triallyl ether, allyl ether compound having such oxirane ring, such as allyl glycidyl ether.
上記2)で用いる乾性油とは、好ましくはヨウ素価１３０以上の油脂で、例えば、アマニ油、大豆油、綿実油、落花生油、やし油等がある。また、エステル交換反応で得られるアルコリシス化合物に用いる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価アルコール、ペンタエリスリトール等の４価アルコールがある。 The drying oil used in the above 2) is preferably an oil having an iodine value of 130 or more, and examples thereof include linseed oil, soybean oil, cottonseed oil, peanut oil, and palm oil. Examples of the polyhydric alcohol used in the alcoholysis compound obtained by the transesterification include trihydric alcohols such as glycerin, trimethylolethane, trimethylolpropane, trishydroxymethylaminomethane, and tetrahydric alcohols such as pentaerythritol. .
上記3)で用いる環状脂肪族不飽和多塩基酸およびその誘導体を含有する化合物としては、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がある。 The compound containing the cycloaliphatic unsaturated polybasic acid and its derivative used in the above 3) is tetrahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, α-terhinene / maleic anhydride adduct And trans-piperylene / maleic anhydride adduct.
4)のジシクロペンタジエニル基を含有する化合物としては、ヒドロキシル化ジシクロペンタジエン等が代表的なものとして挙げられる。 Typical examples of the compound (4) containing a dicyclopentadienyl group include hydroxylated dicyclopentadiene.
本発明に使用する重合性単量体（Ｂ）としては、例えばスチレン、ヒドロキシエチルメタクリレート、（メタ）アクリル酸、（メタ）アクリル酸メチル、（メタ）アクリル酸エチル、（メタ）アクリル酸プロピル、（メタ）アクリル酸イソプロピル、（メタ）アクリル酸ブチル、（メタ）アクリル酸イソブチル、（メタ）アクリル酸シクロヘキシル、フェノキシエチルメタクリレート等の（メタ）アクリル酸誘導体が挙げられる。さらには必要に応じ、エチレングリコールジメタクリレート、ジエチレングリコールジメタクリレートなどの多官能重合性単量体を併用することもできる。 Examples of the polymerizable monomer (B) used in the present invention include styrene, hydroxyethyl methacrylate, (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, Examples include (meth) acrylic acid derivatives such as isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, cyclohexyl (meth) acrylate, and phenoxyethyl methacrylate. Furthermore, if necessary, polyfunctional polymerizable monomers such as ethylene glycol dimethacrylate and diethylene glycol dimethacrylate can be used in combination.
本発明に使用する熱可塑性樹脂（Ｃ）としては、例えばスチレン、塩化ビニル、酢酸ビニル、フマル酸エステル、（メタ）アクリル酸エステル類を重合せしめたものが挙げられ、これらを単独又は二種以上併用して用いられる。これらのうち、好ましくは（メタ）アクリル酸メチルを主成分として重合せしめたものが望ましい。 Examples of the thermoplastic resin (C) used in the present invention include those obtained by polymerizing styrene, vinyl chloride, vinyl acetate, fumaric acid ester, (meth) acrylic acid ester, and these are used alone or in combination of two or more. Used in combination. Of these, those obtained by polymerizing methyl (meth) acrylate as a main component are preferable.
熱可塑性樹脂（Ｃ）の分子量は数平均分子量５，０００〜２００，０００であり、８，０００〜５０，０００が好ましい。５，０００未満の数平均分子量のものでは、十分な表面乾燥性と耐汚れ性を発揮できない。 The molecular weight of the thermoplastic resin (C) is a number average molecular weight of 5,000 to 200,000, preferably 8,000 to 50,000. Those having a number average molecular weight of less than 5,000 cannot exhibit sufficient surface drying properties and stain resistance.
本発明に使用する（Ａ）、（Ｂ）および（Ｃ）の割合は所望の用途によって変更可能であり、特に制限されるものではないが、作業性及び得られる効果から、（Ａ）：（Ｂ）は重量比で１０〜８０：９０〜２０が望ましく、さらに好ましくは４０〜７０：６０〜３０で使用される。また、（Ｃ）の割合は（Ａ）＋（Ｂ）の１００重量部に対して０．１重量部以上であり、好ましくは３重量部以上である。 The ratio of (A), (B) and (C) used in the present invention can be changed depending on the desired application and is not particularly limited. However, from the viewpoint of workability and obtained effects, (A) :( B) is preferably 10 to 80:90 to 20 by weight, and more preferably 40 to 70:60 to 30. Further, the ratio of (C) is 0.1 parts by weight or more, preferably 3 parts by weight or more with respect to 100 parts by weight of (A) + (B).
本発明の舗装材は、（Ａ）ビニルエステル樹脂、ビニルウレタン樹脂、不飽和ポリエステル樹脂から選ばれる少なくとも１種の樹脂、（Ｂ）重合性単量体、（Ｃ）数平均分子量が５，０００〜２００，０００の熱可塑性樹脂及び（Ｄ）骨材を必須成分とするものである。
本発明に使用する骨材（Ｄ）は、例えば、珪砂、川砂、寒水石、大理石屑、砕石、水硬性ケイ酸塩材料、炭酸カルシウム粉、クレー、アルミナ粉、珪石粉、タルク、硫酸バリウム、シリカパウダー、ガラス粉、ガラスビーズ、マイカ、水酸化アルミニウム等が挙げられる。
The paving material of the present invention has (A) at least one resin selected from vinyl ester resins, vinyl urethane resins, and unsaturated polyester resins, (B) a polymerizable monomer, and (C) a number average molecular weight of 5,000. ˜200,000 thermoplastic resin and (D) aggregate are essential components.
The aggregate (D) used in the present invention is, for example, silica sand, river sand, cryolite, marble waste, crushed stone, hydraulic silicate material, calcium carbonate powder, clay, alumina powder, silica powder, talc, barium sulfate, Examples thereof include silica powder, glass powder, glass beads, mica, and aluminum hydroxide.
骨材（Ｄ）の配合割合は（Ａ）＋（Ｂ）＋（Ｃ）の合計１００重量部に対して、１０〜９００重量部添加することができ、５０〜５００重量部用いることが好ましい。 The blending ratio of the aggregate (D) can be added in an amount of 10 to 900 parts by weight, preferably 50 to 500 parts by weight, based on a total of 100 parts by weight of (A) + (B) + (C).
本発明における成分（Ａ）（Ｂ）及び（Ｃ）を必須成分とする土木建築材用被覆組成物及び舗装材には必要に応じ、パラフィンワックス、分散剤、揺変剤、有機酸金属石鹸類、及び重合禁止剤を添加することができる。 As necessary, the coating composition for civil engineering and building materials and the paving material containing the components (A), (B) and (C) as essential components in the present invention, paraffin wax, dispersant, thixotropic agent, organic acid metal soaps , And a polymerization inhibitor can be added.
本発明の土木建築材用被覆組成物及び舗装材を硬化させるためにラジカル硬化剤、光ラジカル開始剤、硬化促進剤を使用することができる。 In order to cure the coating composition for civil engineering and building materials and the paving material of the present invention, a radical curing agent, a photo radical initiator, and a curing accelerator can be used.
ラジカル硬化剤としては、例えば有機過酸化物が挙げられる。具体的にはジアシルパーオキサイド系、パーオキシエステル系、ハイドロパーオキサイド系、ジアルキルパーオキサイド系、ケトンパーオキサイド系、パーオキシケタール系、アルキルパーエステル系、パーカーボネート系等公知公用のものが挙げられる。 Examples of radical curing agents include organic peroxides. Specific examples include known and publicly available ones such as diacyl peroxides, peroxyesters, hydroperoxides, dialkyl peroxides, ketone peroxides, peroxyketals, alkyl peresters, and carbonates. .
光ラジカル開始剤は、光増感剤であり、具体的にはベンゾインアルキルエーテルのようなベンゾインエーテル系やベンゾフェノン等が挙げられる。 The photo radical initiator is a photo sensitizer, and specific examples include benzoin ethers such as benzoin alkyl ethers and benzophenone.
硬化促進剤としては、例えばナフテン酸コバルト、オクチル酸コバルト等の金属石鹸類やコバルトアセチルアセテートのような金属キレート類、アニリンやＮ，Ｎ−ジメチルアニリン等のＮ，Ｎ−置換アニリン類等が挙げられる。これらのうち、アニリン系、金属石鹸系硬化促進剤が好ましい。本発明においてはアミン系、金属石鹸系促進剤が好ましい。 硬化促進剤は２種以上の組み合わせで使用しても良い。また予め樹脂に添加しておいても良いし、使用時に添加しても良い。 Examples of the curing accelerator include metal soaps such as cobalt naphthenate and cobalt octylate, metal chelates such as cobalt acetyl acetate, and N, N-substituted anilines such as aniline and N, N-dimethylaniline. It is done. Of these, aniline-based and metal soap-based curing accelerators are preferred. In the present invention, amine-based and metal soap-based accelerators are preferred. You may use a hardening accelerator in the combination of 2 or more types. Further, it may be added to the resin in advance or may be added at the time of use.
硬化剤の添加量は、成分（Ａ）＋（Ｂ）＋（Ｃ）の被覆組成物の合計量１００重量部に対して０．１〜６重量部であることが好ましい。また硬化促進剤の添加量は、０．１〜５重量部使用する。 It is preferable that the addition amount of a hardening | curing agent is 0.1-6 weight part with respect to 100 weight part of total amounts of the coating composition of component (A) + (B) + (C). Moreover, 0.1-5 weight part is used for the addition amount of a hardening accelerator.
本発明の土木建築材用被覆組成物は、コンクリートやアスファルト等の被覆材料として用いられ、具体的には床材、コーキング材、舗装材、ライニング材、及び型枠用等、土木建築用に用いられる。
また本発明の舗装材は、コンクリートやアスファルト等の舗装、特にトップコート舗装として好ましく用いられる。
The coating composition for civil engineering and building materials of the present invention is used as a coating material for concrete, asphalt, and the like, specifically for flooring, caulking materials, paving materials, lining materials and formwork, etc. It is done.
The pavement material of the present invention is preferably used as a pavement such as concrete or asphalt, particularly as a top coat pavement.
本発明の舗装体は、前記舗装材をコンクリートやアスファルト等の舗装面に塗布し、硬化させることにより得られる。塗装面に塗布する方法としては、舗装面にスプレーする方法、ゴムレーキ等で流し延べて均一に塗布する方法等がある。また塗布する際、アスファルトコンクリート舗装面には直に塗布することができるが、セメントコンクリート舗装や、鋼板上に塗布する場合はプライマー処理を行った上塗布することが好ましい。 The pavement of the present invention is obtained by applying the pavement material to a pavement surface such as concrete or asphalt and curing it. As a method of applying to the painted surface, there are a method of spraying on the pavement surface, a method of applying evenly with a rubber rake, and the like. Moreover, when apply | coating, although it can apply | coat directly on an asphalt concrete pavement surface, when applying on a cement concrete pavement or a steel plate, it is preferable to apply after performing a primer process.
以下本発明を実施例によって更に詳細に説明するが、本発明はこれらの実施例に限定されるものではない。また、文中「部」とあるのは、重量部を示すものである。 EXAMPLES Hereinafter, although an Example demonstrates this invention still in detail, this invention is not limited to these Examples. Also, “parts” in the text indicates parts by weight.
（実施例１）
ビニルエステル樹脂のメタクリル酸メチル溶液であるＨＴＰ−５０２Ｗ［大日本インキ化学工業(株)製］８０重量部に、予め数平均分子量が約１０，０００のポリメタクリル酸メチル３０％のメタクリル酸メチル溶液を２０重量部加え攪拌混合した。これに硬化剤としてベンゾイルパーオキサイドを１．５重量部加え十分に攪拌混合し、被覆組成物を得た。この被覆組成物について乾燥性と耐汚れ性の試験を行った。結果は表−１に示す。
(Example 1)
80 parts by weight of HTP-502W (manufactured by Dainippon Ink & Chemicals, Inc.), which is a methyl methacrylate solution of vinyl ester resin, is a 30% polymethyl methacrylate solution having a number average molecular weight of about 10,000 in advance. 20 parts by weight was added and mixed with stirring. To this was added 1.5 parts by weight of benzoyl peroxide as a curing agent, and the mixture was sufficiently stirred and mixed to obtain a coating composition. This coating composition was tested for drying and stain resistance. The results are shown in Table-1.
（実施例２）
ビニルエステル樹脂としてＨＴＰ−５６３Ｗ［大日本インキ化学工業(株)製］を用いること以外は実施例１と同様に評価を行った。
(Example 2)
Evaluation was performed in the same manner as in Example 1 except that HTP-563W [manufactured by Dainippon Ink & Chemicals, Inc.] was used as the vinyl ester resin.
（実施例３）
ウレタンアクリレート樹脂としてＶＵ−１８０［大日本インキ化学工業(株)製］を用いること以外は実施例１と同様に評価を行った。
(Example 3)
Evaluation was performed in the same manner as in Example 1 except that VU-180 [Dainippon Ink Chemical Co., Ltd.] was used as the urethane acrylate resin.
（実施例４）
ビニルエステル樹脂として空乾成分を有しないＨＴＰ−５０６Ｗ［大日本インキ化学工業(株)製］を用いること以外は実施例１と同様に評価を行った。
Example 4
Evaluation was performed in the same manner as in Example 1 except that HTP-506W (produced by Dainippon Ink & Chemicals, Inc.) having no air-drying component was used as the vinyl ester resin.
（実施例５）
実施例２の被覆組成物１００重量部に対して７号珪砂を１００重量部添加して十分攪拌を行った後、５ｍｍ厚に塗布し硬化させたものについて同様に乾燥性と耐汚れ性を確認した。
(Example 5)
After 100 parts by weight of No. 7 silica sand was added to 100 parts by weight of the coating composition of Example 2 and sufficiently stirred, drying and soil resistance were similarly confirmed for those coated and cured to a thickness of 5 mm. did.
（比較例１〜５）
前記実施例１〜５の被覆組成物のうち、ポリメタクリル酸メチルを除いた以外、前記実施例と同様の操作を行い硬化させたものについて、乾燥性と耐汚れ性を確認した。その結果を表−２に示す。
（比較例６）
前記実施例の被覆組成物の数平均分子量が１０，０００のポリメタクリル酸メチルを数平均分子量が４，０００のポリメタクリル酸メチルに代えた以外は実施例１と同様に操作を行い、評価を行った。
(Comparative Examples 1-5)
Of the coating compositions of Examples 1 to 5, except for polymethylmethacrylate, the same operations as in the above example were performed and cured, and the drying property and stain resistance were confirmed. The results are shown in Table-2.
(Comparative Example 6)
Evaluation was performed in the same manner as in Example 1 except that polymethyl methacrylate having a number average molecular weight of 10,000 in the coating composition of the above example was replaced with polymethyl methacrylate having a number average molecular weight of 4,000. .
［乾燥性と耐汚れ性の試験及び評価］
実施例１で得られた混合物を０．５ｍｍアプリケーターにて、スレート板に塗布し、その塗膜の硬化時の指触乾燥性と耐汚れ性を確認した。
指触乾燥性については、硬化剤を投入してから２時間経過した後の塗膜を手で触ってべたつきの有無を確認した。べたつきが認められないものを「タックなし」、べたつきが認められるものを「タックあり」とした。
また、耐汚れ性については、塗膜にゴム片をこすりつけその際の汚れを５段階で評価した。汚れがつかないものを「５」、ほとんど汚れないものを「４」、汚れるが布で拭き取れるものを「３」、拭き取れずわずかに残るものを「２」、黒く汚れが残るものを「１」とした。
[Dry and stain resistance test and evaluation]
The mixture obtained in Example 1 was applied to a slate plate with a 0.5 mm applicator, and the touch-drying property and stain resistance when the coating film was cured were confirmed.
Regarding the dryness to touch, the presence or absence of stickiness was confirmed by touching the coating film after 2 hours had passed since the curing agent was added. The case where no stickiness was recognized was “no tack”, and the case where stickiness was recognized was “tack”.
Moreover, about stain resistance, the rubber | gum at the time of rubbing a rubber piece to a coating film was evaluated in five steps. "5" for non-stained material, "4" for almost non-stained material, "3" for soiled but wiped with a cloth, "2" for slightly unsuccessfully wiped, and "1" for blackly soiled "
Claims (7)
A pavement formed by applying the pavement material according to claim 5 or 6 to a pavement surface and curing it.
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| JP2003335178A JP4378608B2 (en) | 2003-09-26 | 2003-09-26 | Covering composition for civil engineering and building materials, paving material and paving body using the same |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007106927A (en) * | 2005-10-14 | 2007-04-26 | Mitsubishi Rayon Co Ltd | Floor coating composition and floor material coated with the coating composition |
| WO2009113401A1 (en) | 2008-03-12 | 2009-09-17 | 昭和高分子株式会社 | Water-based binder composition for paving and method of treating pavement surface with the same |
| US9284593B2 (en) | 2009-12-30 | 2016-03-15 | 3M Innovative Properties Company | Live bioload detection using microparticles |
| US9382570B2 (en) | 2008-12-31 | 2016-07-05 | 3M Innovative Properties Company | Live bioload detection using microparticles |
| JP2016204512A (en) * | 2015-04-22 | 2016-12-08 | Dic株式会社 | Primer for civil engineering and floor slab waterproof structure |
| JP2016204511A (en) * | 2015-04-22 | 2016-12-08 | Dic株式会社 | Primer for civil engineering and floor slab waterproof structure |
-
2003
- 2003-09-26 JP JP2003335178A patent/JP4378608B2/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007106927A (en) * | 2005-10-14 | 2007-04-26 | Mitsubishi Rayon Co Ltd | Floor coating composition and floor material coated with the coating composition |
| WO2009113401A1 (en) | 2008-03-12 | 2009-09-17 | 昭和高分子株式会社 | Water-based binder composition for paving and method of treating pavement surface with the same |
| JP2009215831A (en) * | 2008-03-12 | 2009-09-24 | Showa Highpolymer Co Ltd | Water-based binder composite for pavement and surface treatment method for pavement surface using it |
| US9382570B2 (en) | 2008-12-31 | 2016-07-05 | 3M Innovative Properties Company | Live bioload detection using microparticles |
| US9284593B2 (en) | 2009-12-30 | 2016-03-15 | 3M Innovative Properties Company | Live bioload detection using microparticles |
| JP2016204512A (en) * | 2015-04-22 | 2016-12-08 | Dic株式会社 | Primer for civil engineering and floor slab waterproof structure |
| JP2016204511A (en) * | 2015-04-22 | 2016-12-08 | Dic株式会社 | Primer for civil engineering and floor slab waterproof structure |
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| JP4378608B2 (en) | 2009-12-09 |
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