JP2013173925A - Hot melt coating composition - Google Patents
Hot melt coating composition Download PDFInfo
- Publication number
- JP2013173925A JP2013173925A JP2013009895A JP2013009895A JP2013173925A JP 2013173925 A JP2013173925 A JP 2013173925A JP 2013009895 A JP2013009895 A JP 2013009895A JP 2013009895 A JP2013009895 A JP 2013009895A JP 2013173925 A JP2013173925 A JP 2013173925A
- Authority
- JP
- Japan
- Prior art keywords
- oxazoline
- coating composition
- hot
- acid
- melt coating
- 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
Links
- 239000008199 coating composition Substances 0.000 title claims abstract description 38
- 238000007757 hot melt coating Methods 0.000 title claims abstract description 32
- 239000011347 resin Substances 0.000 claims abstract description 64
- 229920005989 resin Polymers 0.000 claims abstract description 64
- 229920000747 poly(lactic acid) Polymers 0.000 claims abstract description 38
- 239000004626 polylactic acid Substances 0.000 claims abstract description 38
- 238000002156 mixing Methods 0.000 claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 12
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims abstract description 10
- 239000011521 glass Substances 0.000 claims abstract description 10
- 239000003086 colorant Substances 0.000 claims abstract description 9
- 239000011324 bead Substances 0.000 claims abstract description 8
- 229930182843 D-Lactic acid Natural products 0.000 claims abstract description 5
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims abstract description 5
- 229940022769 d- lactic acid Drugs 0.000 claims abstract description 5
- -1 carbodiimide compound Chemical class 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 239000004014 plasticizer Substances 0.000 claims description 16
- 239000002981 blocking agent Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 11
- 239000004593 Epoxy Substances 0.000 claims description 9
- 239000000945 filler Substances 0.000 claims description 9
- 230000007613 environmental effect Effects 0.000 abstract description 10
- 239000003973 paint Substances 0.000 description 23
- 239000003208 petroleum Substances 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000010276 construction Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000012943 hotmelt Substances 0.000 description 5
- 150000003949 imides Chemical class 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 3
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- YWOIQIYQBRDOQA-UHFFFAOYSA-N 5,6-dihydro-4h-1,3-oxazine Chemical compound C1COC=NC1 YWOIQIYQBRDOQA-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
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 238000007580 dry-mixing Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- BOSWPVRACYJBSJ-UHFFFAOYSA-N 1,3-di(p-tolyl)carbodiimide Chemical compound C1=CC(C)=CC=C1N=C=NC1=CC=C(C)C=C1 BOSWPVRACYJBSJ-UHFFFAOYSA-N 0.000 description 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- DUILGEYLVHGSEE-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1CO1 DUILGEYLVHGSEE-UHFFFAOYSA-N 0.000 description 2
- HMOZDINWBHMBSQ-UHFFFAOYSA-N 2-[3-(4,5-dihydro-1,3-oxazol-2-yl)phenyl]-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC(C=2OCCN=2)=C1 HMOZDINWBHMBSQ-UHFFFAOYSA-N 0.000 description 2
- ZDNUPMSZKVCETJ-UHFFFAOYSA-N 2-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenyl]-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=C(C=2OCCN=2)C=C1 ZDNUPMSZKVCETJ-UHFFFAOYSA-N 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- FMHKPLXYWVCLME-UHFFFAOYSA-N 4-hydroxy-valeric acid Chemical compound CC(O)CCC(O)=O FMHKPLXYWVCLME-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 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
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-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
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 239000001023 inorganic pigment Substances 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
- 150000002596 lactones Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- HEYRRRCRGGOAJP-UHFFFAOYSA-N n'-(2-methylphenyl)-n-phenylmethanediimine Chemical compound CC1=CC=CC=C1N=C=NC1=CC=CC=C1 HEYRRRCRGGOAJP-UHFFFAOYSA-N 0.000 description 2
- CMESPBFFDMPSIY-UHFFFAOYSA-N n,n'-diphenylmethanediimine Chemical compound C1=CC=CC=C1N=C=NC1=CC=CC=C1 CMESPBFFDMPSIY-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 150000004893 oxazines Chemical class 0.000 description 2
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-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
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910052604 silicate mineral Inorganic materials 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 235000014692 zinc oxide Nutrition 0.000 description 2
- DYJIIMFHSZKBDY-UHFFFAOYSA-N (3-benzoyloxy-2,2-dimethylpropyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC(C)(C)COC(=O)C1=CC=CC=C1 DYJIIMFHSZKBDY-UHFFFAOYSA-N 0.000 description 1
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 1
- SCRCZNMJAVGGEI-UHFFFAOYSA-N 1,4-dioxane-2,5-dione;oxepan-2-one Chemical compound O=C1COC(=O)CO1.O=C1CCCCCO1 SCRCZNMJAVGGEI-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- QBUXRIUNFDMSAK-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)-3-propylpyrrolidine-2,5-dione Chemical compound O=C1C(CCC)CC(=O)N1CC1OC1 QBUXRIUNFDMSAK-UHFFFAOYSA-N 0.000 description 1
- KTCCGEXQRZSXIJ-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1OC1 KTCCGEXQRZSXIJ-UHFFFAOYSA-N 0.000 description 1
- QVNQWADZKGITKV-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1CC1OC1 QVNQWADZKGITKV-UHFFFAOYSA-N 0.000 description 1
- UYLNEXRLQPVSOZ-UHFFFAOYSA-N 1-[3-(hydroxymethyl)-2,2,5,5-tetramethylpyrrol-1-yl]ethanone Chemical compound CC(=O)N1C(C)(C)C=C(CO)C1(C)C UYLNEXRLQPVSOZ-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
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- BLPURQSRCDKZNX-UHFFFAOYSA-N 2,4,6-tris(oxiran-2-ylmethoxy)-1,3,5-triazine Chemical compound C1OC1COC(N=C(OCC1OC1)N=1)=NC=1OCC1CO1 BLPURQSRCDKZNX-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
- SYCNOGATASJMGD-UHFFFAOYSA-N 2-(2-ethylphenoxy)-4,5-dihydro-1,3-oxazole Chemical compound CCC1=CC=CC=C1OC1=NCCO1 SYCNOGATASJMGD-UHFFFAOYSA-N 0.000 description 1
- PUXQRANMBDAMBR-UHFFFAOYSA-N 2-(2-ethylphenyl)-4,5-dihydro-1,3-oxazole Chemical compound CCC1=CC=CC=C1C1=NCCO1 PUXQRANMBDAMBR-UHFFFAOYSA-N 0.000 description 1
- FOCSWKJNNDKQBA-UHFFFAOYSA-N 2-(2-methylphenyl)-4,5-dihydro-1,3-oxazole Chemical compound CC1=CC=CC=C1C1=NCCO1 FOCSWKJNNDKQBA-UHFFFAOYSA-N 0.000 description 1
- NOWGDLPFFKREDH-UHFFFAOYSA-N 2-(2-phenylphenoxy)-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1OC1=CC=CC=C1C1=CC=CC=C1 NOWGDLPFFKREDH-UHFFFAOYSA-N 0.000 description 1
- AZQQFCSRBIOXMN-UHFFFAOYSA-N 2-(2-phenylphenyl)-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1C1=CC=CC=C1 AZQQFCSRBIOXMN-UHFFFAOYSA-N 0.000 description 1
- DMMCPTYEVHKJLH-UHFFFAOYSA-N 2-(2-propylphenoxy)-4,5-dihydro-1,3-oxazole Chemical compound CCCC1=CC=CC=C1OC1=NCCO1 DMMCPTYEVHKJLH-UHFFFAOYSA-N 0.000 description 1
- DZIFWNPTTNYNQP-UHFFFAOYSA-N 2-(2-propylphenyl)-4,5-dihydro-1,3-oxazole Chemical compound CCCC1=CC=CC=C1C1=NCCO1 DZIFWNPTTNYNQP-UHFFFAOYSA-N 0.000 description 1
- REAYNXWAFFVXPQ-UHFFFAOYSA-N 2-(3-ethylphenoxy)-4,5-dihydro-1,3-oxazole Chemical compound CCC1=CC=CC(OC=2OCCN=2)=C1 REAYNXWAFFVXPQ-UHFFFAOYSA-N 0.000 description 1
- LKZCPRJWYIJTAN-UHFFFAOYSA-N 2-(3-ethylphenyl)-4,5-dihydro-1,3-oxazole Chemical compound CCC1=CC=CC(C=2OCCN=2)=C1 LKZCPRJWYIJTAN-UHFFFAOYSA-N 0.000 description 1
- XNYYBTGERQHGNO-UHFFFAOYSA-N 2-(3-propylphenoxy)-4,5-dihydro-1,3-oxazole Chemical compound CCCC1=CC=CC(OC=2OCCN=2)=C1 XNYYBTGERQHGNO-UHFFFAOYSA-N 0.000 description 1
- KLHRMHYYCBOPTN-UHFFFAOYSA-N 2-(3-propylphenyl)-4,5-dihydro-1,3-oxazole Chemical compound CCCC1=CC=CC(C=2OCCN=2)=C1 KLHRMHYYCBOPTN-UHFFFAOYSA-N 0.000 description 1
- KKKKCPPTESQGQH-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-yl)-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=NCCO1 KKKKCPPTESQGQH-UHFFFAOYSA-N 0.000 description 1
- JTWOISPQRQYYAI-UHFFFAOYSA-N 2-(4-phenylphenoxy)-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1OC1=CC=C(C=2C=CC=CC=2)C=C1 JTWOISPQRQYYAI-UHFFFAOYSA-N 0.000 description 1
- NFWNHOGOQVTTRW-UHFFFAOYSA-N 2-(4-phenylphenyl)-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 NFWNHOGOQVTTRW-UHFFFAOYSA-N 0.000 description 1
- AQKDHKMSMBGJLX-UHFFFAOYSA-N 2-(5,6-dihydro-4h-1,3-oxazin-2-ylmethyl)-5,6-dihydro-4h-1,3-oxazine Chemical compound N=1CCCOC=1CC1=NCCCO1 AQKDHKMSMBGJLX-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- ZXJBWUAALADCRI-UHFFFAOYSA-N 2-(octadecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCCCCCOCC1CO1 ZXJBWUAALADCRI-UHFFFAOYSA-N 0.000 description 1
- GKBGCVILKYKJIA-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound O=C1C2CCCCC2C(=O)N1CC1CO1 GKBGCVILKYKJIA-UHFFFAOYSA-N 0.000 description 1
- ZAWQXYPBFKPQLD-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound O=C1C2CC=CCC2C(=O)N1CC1CO1 ZAWQXYPBFKPQLD-UHFFFAOYSA-N 0.000 description 1
- DNVXWIINBUTFEP-UHFFFAOYSA-N 2-[(2-phenylphenoxy)methyl]oxirane Chemical compound C1OC1COC1=CC=CC=C1C1=CC=CC=C1 DNVXWIINBUTFEP-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- KMJHEUHUGMDAIY-UHFFFAOYSA-N 2-[10-(4,5-dihydro-1,3-oxazol-2-yl)decyl]-4,5-dihydro-1,3-oxazole Chemical compound N=1CCOC=1CCCCCCCCCCC1=NCCO1 KMJHEUHUGMDAIY-UHFFFAOYSA-N 0.000 description 1
- KFNAHVKJFHDCSK-UHFFFAOYSA-N 2-[2-(4,5-dihydro-1,3-oxazol-2-yl)ethyl]-4,5-dihydro-1,3-oxazole Chemical compound N=1CCOC=1CCC1=NCCO1 KFNAHVKJFHDCSK-UHFFFAOYSA-N 0.000 description 1
- VOGDKZZTBPDRBD-UHFFFAOYSA-N 2-[2-(4,5-dihydro-1,3-oxazol-2-yl)phenyl]-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1C1=NCCO1 VOGDKZZTBPDRBD-UHFFFAOYSA-N 0.000 description 1
- GXZDWSHVIFZOTG-UHFFFAOYSA-N 2-[2-(5,6-dihydro-4h-1,3-oxazin-2-yl)ethyl]-5,6-dihydro-4h-1,3-oxazine Chemical compound N=1CCCOC=1CCC1=NCCCO1 GXZDWSHVIFZOTG-UHFFFAOYSA-N 0.000 description 1
- JEYLQCXBYFQJRO-UHFFFAOYSA-N 2-[2-[2-(2-ethylbutanoyloxy)ethoxy]ethoxy]ethyl 2-ethylbutanoate Chemical compound CCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CC JEYLQCXBYFQJRO-UHFFFAOYSA-N 0.000 description 1
- XGWUSEZPTVEGQI-UHFFFAOYSA-N 2-[3-(5,6-dihydro-4h-1,3-oxazin-2-yl)phenyl]-5,6-dihydro-4h-1,3-oxazine Chemical compound C1CCOC(C=2C=C(C=CC=2)C=2OCCCN=2)=N1 XGWUSEZPTVEGQI-UHFFFAOYSA-N 0.000 description 1
- UMWUESWLHCAWKP-UHFFFAOYSA-N 2-[4-(4,4-dimethyl-5h-1,3-oxazol-2-yl)butyl]-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(CCCCC=2OCC(C)(C)N=2)=N1 UMWUESWLHCAWKP-UHFFFAOYSA-N 0.000 description 1
- GATDZUUWVARTOQ-UHFFFAOYSA-N 2-[4-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC(C=2C=CC(=CC=2)C=2OCC(C)(C)N=2)=N1 GATDZUUWVARTOQ-UHFFFAOYSA-N 0.000 description 1
- GZQKJQLFIGBEIE-UHFFFAOYSA-N 2-[4-(4,5-dihydro-1,3-oxazol-2-yl)butyl]-4,5-dihydro-1,3-oxazole Chemical compound N=1CCOC=1CCCCC1=NCCO1 GZQKJQLFIGBEIE-UHFFFAOYSA-N 0.000 description 1
- VRRKNSMODVXFPP-UHFFFAOYSA-N 2-[4-(5,6-dihydro-4h-1,3-oxazin-2-yl)butyl]-5,6-dihydro-4h-1,3-oxazine Chemical compound N=1CCCOC=1CCCCC1=NCCCO1 VRRKNSMODVXFPP-UHFFFAOYSA-N 0.000 description 1
- XUMZVELBFAWULJ-UHFFFAOYSA-N 2-[4-(5,6-dihydro-4h-1,3-oxazin-2-yl)phenyl]-5,6-dihydro-4h-1,3-oxazine Chemical compound C1CCOC(C=2C=CC(=CC=2)C=2OCCCN=2)=N1 XUMZVELBFAWULJ-UHFFFAOYSA-N 0.000 description 1
- LDXQWLJXDIZULP-UHFFFAOYSA-N 2-[6-(4,5-dihydro-1,3-oxazol-2-yl)hexyl]-4,5-dihydro-1,3-oxazole Chemical compound N=1CCOC=1CCCCCCC1=NCCO1 LDXQWLJXDIZULP-UHFFFAOYSA-N 0.000 description 1
- ZGLLSGUTQWMHRK-UHFFFAOYSA-N 2-[6-(5,6-dihydro-4h-1,3-oxazin-2-yl)hexyl]-5,6-dihydro-4h-1,3-oxazine Chemical compound N=1CCCOC=1CCCCCCC1=NCCCO1 ZGLLSGUTQWMHRK-UHFFFAOYSA-N 0.000 description 1
- MPPNPBNSYXFIBF-UHFFFAOYSA-N 2-[8-(4,5-dihydro-1,3-oxazol-2-yl)octyl]-4,5-dihydro-1,3-oxazole Chemical compound N=1CCOC=1CCCCCCCCC1=NCCO1 MPPNPBNSYXFIBF-UHFFFAOYSA-N 0.000 description 1
- HIGURUTWFKYJCH-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C1OC1COCC1(COCC2OC2)CCCCC1 HIGURUTWFKYJCH-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- OBLOHLFZRFMBQO-UHFFFAOYSA-N 2-but-2-enoxy-4,5-dihydro-1,3-oxazole Chemical compound CC=CCOC1=NCCO1 OBLOHLFZRFMBQO-UHFFFAOYSA-N 0.000 description 1
- GGANLPLOCUAHSC-UHFFFAOYSA-N 2-but-2-enoxy-5,6-dihydro-4h-1,3-oxazine Chemical compound CC=CCOC1=NCCCO1 GGANLPLOCUAHSC-UHFFFAOYSA-N 0.000 description 1
- XUAHRUIJBNRZGN-UHFFFAOYSA-N 2-but-2-enyl-4,5-dihydro-1,3-oxazole Chemical compound CC=CCC1=NCCO1 XUAHRUIJBNRZGN-UHFFFAOYSA-N 0.000 description 1
- JUDSDRJLVSYYQV-UHFFFAOYSA-N 2-butoxy-4,5-dihydro-1,3-oxazole Chemical compound CCCCOC1=NCCO1 JUDSDRJLVSYYQV-UHFFFAOYSA-N 0.000 description 1
- WQRSOLVWJWZCSH-UHFFFAOYSA-N 2-butoxy-5,6-dihydro-4h-1,3-oxazine Chemical compound CCCCOC1=NCCCO1 WQRSOLVWJWZCSH-UHFFFAOYSA-N 0.000 description 1
- VERUITIRUQLVOC-UHFFFAOYSA-N 2-butyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCC1=NCCO1 VERUITIRUQLVOC-UHFFFAOYSA-N 0.000 description 1
- ZKTPGXSTOJXHIG-UHFFFAOYSA-N 2-cyclohexyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1CCCCC1 ZKTPGXSTOJXHIG-UHFFFAOYSA-N 0.000 description 1
- JIXIPZRYCDIKSW-UHFFFAOYSA-N 2-cyclohexyloxy-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1OC1CCCCC1 JIXIPZRYCDIKSW-UHFFFAOYSA-N 0.000 description 1
- ARCMWAPXBLLDFD-UHFFFAOYSA-N 2-cyclohexyloxy-5,6-dihydro-4h-1,3-oxazine Chemical compound C1CCCCC1OC1=NCCCO1 ARCMWAPXBLLDFD-UHFFFAOYSA-N 0.000 description 1
- DAWATBBPYSKHNE-UHFFFAOYSA-N 2-cyclopentyloxy-4,5-dihydro-1,3-oxazole Chemical compound C1CCCC1OC1=NCCO1 DAWATBBPYSKHNE-UHFFFAOYSA-N 0.000 description 1
- HMTQOKDBFUQMHB-UHFFFAOYSA-N 2-cyclopentyloxy-5,6-dihydro-4h-1,3-oxazine Chemical compound C1CCCC1OC1=NCCCO1 HMTQOKDBFUQMHB-UHFFFAOYSA-N 0.000 description 1
- XNUTWTLINYKVBC-UHFFFAOYSA-N 2-decoxy-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCCOC1=NCCO1 XNUTWTLINYKVBC-UHFFFAOYSA-N 0.000 description 1
- NUNKLRNANFBFIP-UHFFFAOYSA-N 2-decyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCCC1=NCCO1 NUNKLRNANFBFIP-UHFFFAOYSA-N 0.000 description 1
- MTYHIWQZNFDCJT-UHFFFAOYSA-N 2-ethoxy-4,5-dihydro-1,3-oxazole Chemical compound CCOC1=NCCO1 MTYHIWQZNFDCJT-UHFFFAOYSA-N 0.000 description 1
- NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 description 1
- BPBBNCOOHBTMFW-UHFFFAOYSA-N 2-heptoxy-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCOC1=NCCO1 BPBBNCOOHBTMFW-UHFFFAOYSA-N 0.000 description 1
- VSIBKVQHWCKRBF-UHFFFAOYSA-N 2-heptoxy-5,6-dihydro-4h-1,3-oxazine Chemical compound CCCCCCCOC1=NCCCO1 VSIBKVQHWCKRBF-UHFFFAOYSA-N 0.000 description 1
- BWDVBMJUJCPESR-UHFFFAOYSA-N 2-heptyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCC1=NCCO1 BWDVBMJUJCPESR-UHFFFAOYSA-N 0.000 description 1
- KQJLGXKIJBWFSB-UHFFFAOYSA-N 2-hexoxy-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCOC1=NCCO1 KQJLGXKIJBWFSB-UHFFFAOYSA-N 0.000 description 1
- BZMFIFUFEAWQTI-UHFFFAOYSA-N 2-hexoxy-5,6-dihydro-4h-1,3-oxazine Chemical compound CCCCCCOC1=NCCCO1 BZMFIFUFEAWQTI-UHFFFAOYSA-N 0.000 description 1
- AADZRTSFCAMLBV-UHFFFAOYSA-N 2-hexyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCC1=NCCO1 AADZRTSFCAMLBV-UHFFFAOYSA-N 0.000 description 1
- LGXBKPPZWLWURH-UHFFFAOYSA-N 2-methoxy-4,5-dihydro-1,3-oxazole Chemical compound COC1=NCCO1 LGXBKPPZWLWURH-UHFFFAOYSA-N 0.000 description 1
- DJKLTPGKMXSIQQ-UHFFFAOYSA-N 2-methoxy-5,6-dihydro-4h-1,3-oxazine Chemical compound COC1=NCCCO1 DJKLTPGKMXSIQQ-UHFFFAOYSA-N 0.000 description 1
- GUXJXWKCUUWCLX-UHFFFAOYSA-N 2-methyl-2-oxazoline Chemical compound CC1=NCCO1 GUXJXWKCUUWCLX-UHFFFAOYSA-N 0.000 description 1
- OVEUFHOBGCSKSH-UHFFFAOYSA-N 2-methyl-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound CC1=CC=CC=C1N(CC1OC1)CC1OC1 OVEUFHOBGCSKSH-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
- GCFOLRJYZFCLHJ-UHFFFAOYSA-N 2-nonoxy-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCOC1=NCCO1 GCFOLRJYZFCLHJ-UHFFFAOYSA-N 0.000 description 1
- OLSSHFICEKRRBV-UHFFFAOYSA-N 2-nonoxy-5,6-dihydro-4h-1,3-oxazine Chemical compound CCCCCCCCCOC1=NCCCO1 OLSSHFICEKRRBV-UHFFFAOYSA-N 0.000 description 1
- OQWAVMKUNIQCFD-UHFFFAOYSA-N 2-nonyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCC1=NCCO1 OQWAVMKUNIQCFD-UHFFFAOYSA-N 0.000 description 1
- HSHQFIJLSKCVFR-UHFFFAOYSA-N 2-octoxy-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCOC1=NCCO1 HSHQFIJLSKCVFR-UHFFFAOYSA-N 0.000 description 1
- ZZNVXFNKSKRYRD-UHFFFAOYSA-N 2-octoxy-5,6-dihydro-4h-1,3-oxazine Chemical compound CCCCCCCCOC1=NCCCO1 ZZNVXFNKSKRYRD-UHFFFAOYSA-N 0.000 description 1
- LRTZAUAUUUURAF-UHFFFAOYSA-N 2-octyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCC1=NCCO1 LRTZAUAUUUURAF-UHFFFAOYSA-N 0.000 description 1
- UZKJKUQQMYNECC-UHFFFAOYSA-N 2-pentoxy-4,5-dihydro-1,3-oxazole Chemical compound CCCCCOC1=NCCO1 UZKJKUQQMYNECC-UHFFFAOYSA-N 0.000 description 1
- XUJPGKCYJIYXPP-UHFFFAOYSA-N 2-pentoxy-5,6-dihydro-4h-1,3-oxazine Chemical compound CCCCCOC1=NCCCO1 XUJPGKCYJIYXPP-UHFFFAOYSA-N 0.000 description 1
- OEENXWLHBPUUFL-UHFFFAOYSA-N 2-pentyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCC1=NCCO1 OEENXWLHBPUUFL-UHFFFAOYSA-N 0.000 description 1
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 1
- XKJTWYJWMOTQQI-UHFFFAOYSA-N 2-propoxy-4,5-dihydro-1,3-oxazole Chemical compound CCCOC1=NCCO1 XKJTWYJWMOTQQI-UHFFFAOYSA-N 0.000 description 1
- DODNHSOFTLNZLP-UHFFFAOYSA-N 2-propoxy-5,6-dihydro-4h-1,3-oxazine Chemical compound CCCOC1=NCCCO1 DODNHSOFTLNZLP-UHFFFAOYSA-N 0.000 description 1
- GXCJLVVUIVSLOQ-UHFFFAOYSA-N 2-propyl-4,5-dihydro-1,3-oxazole Chemical compound CCCC1=NCCO1 GXCJLVVUIVSLOQ-UHFFFAOYSA-N 0.000 description 1
- ULKFLOVGORAZDI-UHFFFAOYSA-N 3,3-dimethyloxetan-2-one Chemical compound CC1(C)COC1=O ULKFLOVGORAZDI-UHFFFAOYSA-N 0.000 description 1
- RDIGYBZNNOGMHU-UHFFFAOYSA-N 3-amino-2,4,5-tris(oxiran-2-ylmethyl)phenol Chemical compound OC1=CC(CC2OC2)=C(CC2OC2)C(N)=C1CC1CO1 RDIGYBZNNOGMHU-UHFFFAOYSA-N 0.000 description 1
- GHHXVIBJFJUWJN-UHFFFAOYSA-N 3-ethyl-1-(oxiran-2-ylmethyl)pyrrolidine-2,5-dione Chemical compound O=C1C(CC)CC(=O)N1CC1OC1 GHHXVIBJFJUWJN-UHFFFAOYSA-N 0.000 description 1
- ZUEKSBNZDDRQKI-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C2=C(Br)C(Br)=C(Br)C(Br)=C2C(=O)N1CC1CO1 ZUEKSBNZDDRQKI-UHFFFAOYSA-N 0.000 description 1
- DLLNCQNGSRCPCP-UHFFFAOYSA-N 4,7-dimethyl-2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C=2C(C)=CC=C(C)C=2C(=O)N1CC1CO1 DLLNCQNGSRCPCP-UHFFFAOYSA-N 0.000 description 1
- CXXSQMDHHYTRKY-UHFFFAOYSA-N 4-amino-2,3,5-tris(oxiran-2-ylmethyl)phenol Chemical compound C1=C(O)C(CC2OC2)=C(CC2OC2)C(N)=C1CC1CO1 CXXSQMDHHYTRKY-UHFFFAOYSA-N 0.000 description 1
- RWGLROKEYRSHME-UHFFFAOYSA-N 4-benzyl-4,5-dihydro-1,3-oxazole Chemical compound C=1C=CC=CC=1CC1COC=N1 RWGLROKEYRSHME-UHFFFAOYSA-N 0.000 description 1
- VITTZDWCUGTYIB-UHFFFAOYSA-N 4-butyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCC1COC=N1 VITTZDWCUGTYIB-UHFFFAOYSA-N 0.000 description 1
- CJFNLGVLNYZLEA-UHFFFAOYSA-N 4-cyclohexyl-4,5-dihydro-1,3-oxazole Chemical compound C1OC=NC1C1CCCCC1 CJFNLGVLNYZLEA-UHFFFAOYSA-N 0.000 description 1
- RWMKXFCUXJWKBU-UHFFFAOYSA-N 4-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1COC=N1 RWMKXFCUXJWKBU-UHFFFAOYSA-N 0.000 description 1
- YTDWINDMGUQTBS-UHFFFAOYSA-N 4-hexyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCC1COC=N1 YTDWINDMGUQTBS-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 229940006015 4-hydroxybutyric acid Drugs 0.000 description 1
- LKAGYEIANFNSPQ-UHFFFAOYSA-N 4-methyl-2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C=2C(C)=CC=CC=2C(=O)N1CC1CO1 LKAGYEIANFNSPQ-UHFFFAOYSA-N 0.000 description 1
- FYQUELMPDYVBFY-UHFFFAOYSA-N 4-methyl-2-[4-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]-4,5-dihydro-1,3-oxazole Chemical compound CC1COC(C=2C=CC(=CC=2)C=2OCC(C)N=2)=N1 FYQUELMPDYVBFY-UHFFFAOYSA-N 0.000 description 1
- IFIUFEBEPGGBIJ-UHFFFAOYSA-N 4-methyl-4,5-dihydro-1,3-oxazole Chemical compound CC1COC=N1 IFIUFEBEPGGBIJ-UHFFFAOYSA-N 0.000 description 1
- KPFFWKFQXBYFJJ-UHFFFAOYSA-N 4-methyl-n-(oxiran-2-ylmethyl)benzamide Chemical compound C1=CC(C)=CC=C1C(=O)NCC1OC1 KPFFWKFQXBYFJJ-UHFFFAOYSA-N 0.000 description 1
- DBTPMQIQJZFVAB-UHFFFAOYSA-N 4-phenyl-4,5-dihydro-1,3-oxazole Chemical compound C1OC=NC1C1=CC=CC=C1 DBTPMQIQJZFVAB-UHFFFAOYSA-N 0.000 description 1
- HLIYUPUYSLFMEB-UHFFFAOYSA-N 4-propyl-4,5-dihydro-1,3-oxazole Chemical compound CCCC1COC=N1 HLIYUPUYSLFMEB-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- YMGPPMCFHDGURN-UHFFFAOYSA-N 5,6-dichloro-2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C=2C=C(Cl)C(Cl)=CC=2C(=O)N1CC1CO1 YMGPPMCFHDGURN-UHFFFAOYSA-N 0.000 description 1
- UHOOWRLQFJCGNU-UHFFFAOYSA-N 5,6-dimethyl-2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C=2C=C(C)C(C)=CC=2C(=O)N1CC1CO1 UHOOWRLQFJCGNU-UHFFFAOYSA-N 0.000 description 1
- DTTPQCNEZBVLSQ-UHFFFAOYSA-N 5-bromo-6-butyl-2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C=2C=C(Br)C(CCCC)=CC=2C(=O)N1CC1CO1 DTTPQCNEZBVLSQ-UHFFFAOYSA-N 0.000 description 1
- OQMNPUKPTLMORJ-UHFFFAOYSA-N 5-chloro-2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC(Cl)=CC=C2C(=O)N1CC1CO1 OQMNPUKPTLMORJ-UHFFFAOYSA-N 0.000 description 1
- AACFNWHTALUANV-UHFFFAOYSA-N 5-ethoxy-2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC(OCC)=CC=C2C(=O)N1CC1CO1 AACFNWHTALUANV-UHFFFAOYSA-N 0.000 description 1
- LSRNPDMDCXGGSD-UHFFFAOYSA-N 5-methyl-2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC(C)=CC=C2C(=O)N1CC1CO1 LSRNPDMDCXGGSD-UHFFFAOYSA-N 0.000 description 1
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- BKKUSQACQFZCNG-UHFFFAOYSA-N CC1=C(C(=C(C=C1)N=C=N)C)C Chemical compound CC1=C(C(=C(C=C1)N=C=N)C)C BKKUSQACQFZCNG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 229910000004 White lead Inorganic materials 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 239000006230 acetylene black Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- FNGGVJIEWDRLFV-UHFFFAOYSA-N anthracene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=CC3=C(C(O)=O)C(C(=O)O)=CC=C3C=C21 FNGGVJIEWDRLFV-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- CJDPJFRMHVXWPT-UHFFFAOYSA-N barium sulfide Chemical compound [S-2].[Ba+2] CJDPJFRMHVXWPT-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical compound C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 description 1
- MRDNMQDAPCZRNE-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) 2-heptadecylpropanedioate Chemical compound C1OC1COC(=O)C(CCCCCCCCCCCCCCCCC)C(=O)OCC1CO1 MRDNMQDAPCZRNE-UHFFFAOYSA-N 0.000 description 1
- VKEFGOTVPWVWCH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) 2-methylbenzene-1,4-dicarboxylate Chemical compound CC1=CC(C(=O)OCC2OC2)=CC=C1C(=O)OCC1CO1 VKEFGOTVPWVWCH-UHFFFAOYSA-N 0.000 description 1
- UBJUCQNZOHGQSR-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) 2-pentylpropanedioate Chemical compound C(C1CO1)OC(=O)C(CCCCC)C(=O)OCC1CO1 UBJUCQNZOHGQSR-UHFFFAOYSA-N 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- ZXOATMQSUNJNNG-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OCC2OC2)=CC=1C(=O)OCC1CO1 ZXOATMQSUNJNNG-UHFFFAOYSA-N 0.000 description 1
- NEPKLUNSRVEBIX-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OCC2OC2)C=CC=1C(=O)OCC1CO1 NEPKLUNSRVEBIX-UHFFFAOYSA-N 0.000 description 1
- JQDCYGOHLMJDNA-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) butanedioate Chemical compound C1OC1COC(=O)CCC(=O)OCC1CO1 JQDCYGOHLMJDNA-UHFFFAOYSA-N 0.000 description 1
- KTPIWUHKYIJBCR-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohex-4-ene-1,2-dicarboxylate Chemical compound C1C=CCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 KTPIWUHKYIJBCR-UHFFFAOYSA-N 0.000 description 1
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 description 1
- NFVGWOSADNLNHZ-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) decanedioate Chemical compound C1OC1COC(=O)CCCCCCCCC(=O)OCC1CO1 NFVGWOSADNLNHZ-UHFFFAOYSA-N 0.000 description 1
- QGTGWZMXYMSFJE-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) dodecanedioate Chemical compound C1OC1COC(=O)CCCCCCCCCCC(=O)OCC1CO1 QGTGWZMXYMSFJE-UHFFFAOYSA-N 0.000 description 1
- KBWLNCUTNDKMPN-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) hexanedioate Chemical compound C1OC1COC(=O)CCCCC(=O)OCC1CO1 KBWLNCUTNDKMPN-UHFFFAOYSA-N 0.000 description 1
- AUNDMQBAPCPNJA-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) naphthalene-1,2-dicarboxylate Chemical compound C=1C=C2C=CC=CC2=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 AUNDMQBAPCPNJA-UHFFFAOYSA-N 0.000 description 1
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BEWFIPLBFJGWSR-UHFFFAOYSA-N butyl 12-acetyloxyoctadec-9-enoate Chemical compound CCCCCCC(OC(C)=O)CC=CCCCCCCCC(=O)OCCCC BEWFIPLBFJGWSR-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000006063 cullet Substances 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- MHIBEGOZTWERHF-UHFFFAOYSA-N heptane-1,1-diol Chemical compound CCCCCCC(O)O MHIBEGOZTWERHF-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 239000006233 lamp black Substances 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- SIDXWBLTDUJVLZ-UHFFFAOYSA-N n'-(2-methylphenyl)-n-octadecylmethanediimine Chemical compound CCCCCCCCCCCCCCCCCCN=C=NC1=CC=CC=C1C SIDXWBLTDUJVLZ-UHFFFAOYSA-N 0.000 description 1
- ZMCAZPFMRNNEPX-UHFFFAOYSA-N n'-(9-octyloctadecan-9-yl)methanediimine Chemical compound CCCCCCCCCC(CCCCCCCC)(CCCCCCCC)N=C=N ZMCAZPFMRNNEPX-UHFFFAOYSA-N 0.000 description 1
- GICIQDIJBUWIEW-UHFFFAOYSA-N n'-benzylmethanediimine Chemical compound N=C=NCC1=CC=CC=C1 GICIQDIJBUWIEW-UHFFFAOYSA-N 0.000 description 1
- JCNCSCMYYGONLU-UHFFFAOYSA-N n,n'-bis(2-methylphenyl)methanediimine Chemical compound CC1=CC=CC=C1N=C=NC1=CC=CC=C1C JCNCSCMYYGONLU-UHFFFAOYSA-N 0.000 description 1
- NZGGUIFHFVGRKD-UHFFFAOYSA-N n,n,2-tribromo-3,4-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CC1=C(Br)C(N(Br)Br)=CC=C1CC1CO1 NZGGUIFHFVGRKD-UHFFFAOYSA-N 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- LTUKBRXELKXITI-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NCC1CO1 LTUKBRXELKXITI-UHFFFAOYSA-N 0.000 description 1
- AWEISZDGELFCIM-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)naphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NCC1CO1 AWEISZDGELFCIM-UHFFFAOYSA-N 0.000 description 1
- LEWFYLHNCUJXQT-UHFFFAOYSA-N n-benzyl-n'-(2-methylphenyl)methanediimine Chemical compound CC1=CC=CC=C1N=C=NCC1=CC=CC=C1 LEWFYLHNCUJXQT-UHFFFAOYSA-N 0.000 description 1
- VQMQCAXAELDDRE-UHFFFAOYSA-N n-benzyl-n'-phenylmethanediimine Chemical compound C=1C=CC=CC=1CN=C=NC1=CC=CC=C1 VQMQCAXAELDDRE-UHFFFAOYSA-N 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- BSIUVPDPDCLYDR-UHFFFAOYSA-N n-cyclohexyl-n'-(2-methylphenyl)methanediimine Chemical compound CC1=CC=CC=C1N=C=NC1CCCCC1 BSIUVPDPDCLYDR-UHFFFAOYSA-N 0.000 description 1
- ATQZPTJEJUAUPY-UHFFFAOYSA-N n-octadecyl-n'-phenylmethanediimine Chemical compound CCCCCCCCCCCCCCCCCCN=C=NC1=CC=CC=C1 ATQZPTJEJUAUPY-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 230000000422 nocturnal effect Effects 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical class NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- LOGTZDQTPQYKEN-HZJYTTRNSA-N oxiran-2-ylmethyl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC1CO1 LOGTZDQTPQYKEN-HZJYTTRNSA-N 0.000 description 1
- SJVUKRJWTDCMSJ-UHFFFAOYSA-N oxiran-2-ylmethyl 4-methylbenzoate Chemical compound C1=CC(C)=CC=C1C(=O)OCC1OC1 SJVUKRJWTDCMSJ-UHFFFAOYSA-N 0.000 description 1
- BEJZOPYRAQVYHS-UHFFFAOYSA-N oxiran-2-ylmethyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OCC1CO1 BEJZOPYRAQVYHS-UHFFFAOYSA-N 0.000 description 1
- PTLZMJYQEBOHHM-UHFFFAOYSA-N oxiran-2-ylmethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC1CO1 PTLZMJYQEBOHHM-UHFFFAOYSA-N 0.000 description 1
- KYVUJPJYTYQNGJ-UHFFFAOYSA-N oxiran-2-ylmethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC1CO1 KYVUJPJYTYQNGJ-UHFFFAOYSA-N 0.000 description 1
- YALCCRLYDDPUAV-UHFFFAOYSA-N oxirane;2-(phenoxymethyl)oxirane Chemical compound C1CO1.C1OC1COC1=CC=CC=C1 YALCCRLYDDPUAV-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- SNDJXNNIVDNYSE-UHFFFAOYSA-N phosphane 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound P.OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O SNDJXNNIVDNYSE-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000765 poly(2-oxazolines) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BPJZKLBPJBMLQG-KWRJMZDGSA-N propanoyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(=O)CC BPJZKLBPJBMLQG-KWRJMZDGSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000009283 thermal hydrolysis Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
Abstract
Description
本発明は、ポリ乳酸樹脂を含有することを特徴とした環境負荷の小さい熱溶融型塗料組成物に関するものである。 The present invention relates to a hot-melt coating composition having a low environmental load, characterized by containing a polylactic acid resin.
近年、自動車、電気機器など様々な分野において、環境負荷低減の要求が高まっている。塗料用途においても、天然素材またはポリ乳酸樹脂に代表されるバイオマス由来原料からなる合成樹脂を利用した商品の開発が盛んに行われている。 In recent years, demands for reducing environmental burdens are increasing in various fields such as automobiles and electrical equipment. In paint applications, products using synthetic resins made of biomass-derived raw materials represented by natural materials or polylactic acid resins are being actively developed.
熱溶融型塗料の代表である道路用標示塗料は、一般的に粘結樹脂、着色顔料、充填剤、可塑剤、ワックス、安定剤、酸化防止剤、およびガラスビーズなどから構成されているが、この粘結樹脂には、未だ石油を原料とする樹脂が使用されている。 Road marking paints, which are representative of hot melt paints, are generally composed of a binder resin, colored pigments, fillers, plasticizers, waxes, stabilizers, antioxidants, glass beads, etc. As the binder resin, a resin made from petroleum is still used.
例えば、特許文献1および特許文献2では、粘結樹脂としてC5留分やC9留分などの石油樹脂を使用することが開示されている。特許文献3では、吹き付け樹脂系用途として、メタクリラート樹脂の使用が開示されている。これらはいずれも石油を原料とする樹脂を使用しているため環境保護効果はなく、より環境負荷の小さい材料への転換が求められていた。 For example, Patent Document 1 and Patent Document 2 disclose the use of petroleum resins such as C5 fraction and C9 fraction as the caking resin. Patent Document 3 discloses the use of a methacrylate resin as a spray resin application. Since all of these use resins made from petroleum, they have no environmental protection effect, and there has been a demand for conversion to materials with less environmental impact.
本発明は、環境負荷の小さい熱溶融型塗料組成物を提供することを課題とする。 An object of the present invention is to provide a hot-melt coating composition having a low environmental load.
本発明者らは、上記課題を解決するために鋭意研究をした結果、熱溶融型塗料組成物の粘結樹脂として、ポリ乳酸樹脂を使用することにより、上記課題が解決されることを見出し、本発明に到達した。 As a result of diligent research to solve the above problems, the present inventors have found that the above problems can be solved by using a polylactic acid resin as a binder resin of a hot-melt coating composition. The present invention has been reached.
すなわち、本発明は以下の通りである。
(1)ポリ乳酸樹脂100重量部に対して、着色剤0.1〜30重量部、反射材1〜50重量部を配合してなる熱溶融型塗料組成物、
(2)ポリ乳酸樹脂の重量平均分子量が10万以下である前記(1)記載の熱溶融型塗料組成物、
(3)ポリ乳酸樹脂に含まれるL−乳酸とD−乳酸の比(L/D)が5/95〜95/5の範囲である前記(1)〜(2)のいずれか記載の熱溶融型塗料組成物、
(4)反射材がガラスビーズである前記(1)〜(3)のいずれか記載の熱溶融型塗料組成物、
(5)前記(1)〜(4)のいずれか記載の組成物に対し、さらに充填剤を配合してなる熱溶融型塗料組成物、
(6)前記(1)〜(5)のいずれか記載の組成物に対し、さらに可塑剤を配合してなる熱溶融型塗料組成物、
(7)前記(1)〜(6)のいずれか記載の組成物に対し、さらにカルボキシル基反応性末端封鎖剤を配合してなる熱溶融型塗料組成物、
(8)前記カルボキシル基反応性末端封鎖剤がエポキシ化合物および/またはカルボジイミド化合物である前記(7)記載の熱溶融型塗料組成物である。
That is, the present invention is as follows.
(1) A hot-melt coating composition comprising 0.1 to 30 parts by weight of a colorant and 1 to 50 parts by weight of a reflective material with respect to 100 parts by weight of a polylactic acid resin,
(2) The hot melt coating composition according to (1), wherein the polylactic acid resin has a weight average molecular weight of 100,000 or less,
(3) The thermal melting according to any one of (1) to (2), wherein the ratio (L / D) of L-lactic acid to D-lactic acid contained in the polylactic acid resin is in the range of 5/95 to 95/5. Mold paint composition,
(4) The hot melt coating composition according to any one of (1) to (3), wherein the reflective material is glass beads,
(5) A hot-melt coating composition obtained by further blending a filler with the composition according to any one of (1) to (4),
(6) A hot-melt coating composition obtained by further blending a plasticizer with the composition according to any one of (1) to (5),
(7) A hot-melt coating composition obtained by further blending a carboxyl group-reactive end-blocking agent with the composition according to any one of (1) to (6),
(8) The hot melt coating composition according to (7), wherein the carboxyl group-reactive end-blocking agent is an epoxy compound and / or a carbodiimide compound.
本発明によれば、以下に説明するとおり、熱溶融型塗料組成物の粘結樹脂として、ポリ乳酸樹脂を使用することにより、環境負荷の小さい熱溶融型塗料組成物を提供することができる。 According to the present invention, as described below, by using a polylactic acid resin as a caking resin for a hot-melt coating composition, a hot-melt coating composition having a small environmental load can be provided.
本発明で使用するポリ乳酸樹脂とは、L−乳酸および/またはD−乳酸を主たる構成成分とするポリマーであるが、乳酸以外の他の共重合成分を含んでいてもよい。かかる他の共重合成分単位としては、例えば、多価カルボン酸、多価アルコール、ヒドロキシカルボン酸、ラクトンなどが挙げられ、具体的には、シュウ酸、マロン酸、コハク酸、グルタル酸、アジピン酸、アゼライン酸、セバシン酸、ドデカンジオン酸、フマル酸、シクロヘキサンジカルボン酸、テレフタル酸、イソフタル酸、フタル酸、2,6−ナフタレンジカルボン酸、アントラセンジカルボン酸、5−ナトリウムスルホイソフタル酸、5−テトラブチルホスホニウムスルホイソフタル酸などの多価カルボン酸類、エチレングリコール、プロピレングリコール、ブタンジオール、ヘプタンジオール、ヘキサンジオール、オクタンジオール、ノナンジオール、デカンジオール、1,4−シクロヘキサンジメタノール、ネオペンチルグリコール、グリセリン、ペンタエリスリトール、ビスフェノールA、ビスフェノールにエチレンオキシドを付加反応させた芳香族多価アルコール、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、ポリプロピレングリコール、ポリテトラメチレングリコールなどの多価アルコール類、グリコール酸、3−ヒドロキシ酪酸、4−ヒドロキシ酪酸、4−ヒドロキシ吉草酸、6−ヒドロキシカプロン酸、ヒドロキシ安息香酸などのヒドロキシカルボン酸類、およびグリコリド、ε−カプロラクトングリコリド、ε−カプロラクトン、β−プロピオラクトン、δ−ブチロラクトン、β−またはγ−ブチロラクトン、ピバロラクトン、δ−バレロラクトンなどのラクトン類などから生成する単位が挙げられる。このような共重合単位は、全単量体単位を100モル%としたときに、通常0〜30モル%の含有量とするのが好ましく、0〜10モル%であることが好ましい。 The polylactic acid resin used in the present invention is a polymer containing L-lactic acid and / or D-lactic acid as a main constituent component, but may contain other copolymerization components other than lactic acid. Examples of such other copolymer component units include polyvalent carboxylic acids, polyhydric alcohols, hydroxycarboxylic acids, lactones, and the like. Specifically, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid , Azelaic acid, sebacic acid, dodecanedioic acid, fumaric acid, cyclohexanedicarboxylic acid, terephthalic acid, isophthalic acid, phthalic acid, 2,6-naphthalenedicarboxylic acid, anthracene dicarboxylic acid, 5-sodium sulfoisophthalic acid, 5-tetrabutyl Polycarboxylic acids such as phosphonium sulfoisophthalic acid, ethylene glycol, propylene glycol, butanediol, heptanediol, hexanediol, octanediol, nonanediol, decanediol, 1,4-cyclohexanedimethanol, neopentylglyco Glycerin, pentaerythritol, bisphenol A, aromatic polyhydric alcohol obtained by addition reaction of bisphenol with ethylene oxide, polyhydric alcohols such as diethylene glycol, triethylene glycol, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, glycolic acid, Hydroxycarboxylic acids such as 3-hydroxybutyric acid, 4-hydroxybutyric acid, 4-hydroxyvaleric acid, 6-hydroxycaproic acid, hydroxybenzoic acid, and glycolide, ε-caprolactone glycolide, ε-caprolactone, β-propiolactone, δ -Units generated from lactones such as butyrolactone, β- or γ-butyrolactone, pivalolactone, and δ-valerolactone. Such a copolymerized unit usually preferably has a content of 0 to 30 mol%, preferably 0 to 10 mol%, when the total monomer units are 100 mol%.
本発明において、ポリ乳酸を構成するL−乳酸とD−乳酸の比(L/D)は、実質的に加工可能であれば特に制限されるものではないが、塗膜の柔軟性を考慮すると、5/95〜95/5の範囲にあることが好ましく、10/90〜90/10の範囲にあることがさらに好ましく、15/85〜85/15の範囲にあることが最も好ましい。 In the present invention, the ratio (L / D) of L-lactic acid and D-lactic acid constituting polylactic acid is not particularly limited as long as it can be processed substantially, but considering the flexibility of the coating film It is preferably in the range of 5/95 to 95/5, more preferably in the range of 10/90 to 90/10, and most preferably in the range of 15/85 to 85/15.
本発明において、ポリ乳酸樹脂の製造方法としては、公知の重合方法を用いることができ、乳酸からの直接重合法およびラクチドを介する開環重合法などを用いることができる。 In the present invention, as a method for producing a polylactic acid resin, a known polymerization method can be used, and a direct polymerization method from lactic acid, a ring-opening polymerization method via lactide, or the like can be used.
本発明において、ポリ乳酸樹脂の分子量や分子量分布は、実質的に加工が可能であれば、特に限定されるものではないが、分子量が低いほど流動性が高くなり施工性が良好であるという観点から、重量平均分子量としては、好ましくは10万以下、さらに好ましくは8万以下、最も好ましくは5万以下であるのが良い。ここでいう重量平均分子量とは、溶媒としてヘキサフルオロイソプロパノールを用いたゲルパーミエーションクロマトグラフィー(GPC)で測定したポリメタクリル酸メチル(PMMA)換算の重量平均分子量である。 In the present invention, the molecular weight and molecular weight distribution of the polylactic acid resin are not particularly limited as long as they can be processed substantially, but the viewpoint that the lower the molecular weight, the higher the fluidity and the better the workability. Therefore, the weight average molecular weight is preferably 100,000 or less, more preferably 80,000 or less, and most preferably 50,000 or less. The weight average molecular weight herein is a weight average molecular weight in terms of polymethyl methacrylate (PMMA) measured by gel permeation chromatography (GPC) using hexafluoroisopropanol as a solvent.
本発明において、ポリ乳酸樹脂の190℃、21.2N荷重条件におけるメルトフローレート(MFR)は、施工性に優れるという点で、5g/10分以上であることが好ましく、50g/10分以上であることがより好ましく、100g/10分以上であることがさらに好ましい。ここでいうメルトフローレートとは、東洋精機製「メルトインデクサー」を用い、JISK7210に従って、190℃、21.2N荷重条件において測定した値のことである。 In the present invention, the melt flow rate (MFR) at 190 ° C. and 21.2N load condition of the polylactic acid resin is preferably 5 g / 10 min or more in terms of excellent workability, and 50 g / 10 min or more. More preferably, it is more preferably 100 g / 10 min or more. The melt flow rate here is a value measured at 190 ° C. under a 21.2N load condition in accordance with JISK7210 using a “melt indexer” manufactured by Toyo Seiki.
本発明で使用される着色剤は、特に限定されることはなく、通常一般的に用いられる無機顔料および有機顔料を用いることができる。無機顔料としては、例えば二酸化チタン、亜鉛華、リトポン、チタンイエロー、鉛白、鉛丹、黄鉛、耐熱黄鉛、複合酸化物系顔料、硫化亜鉛、酸化亜鉛、硫化バリウム、酸化鉄、群青、紺青、コバルトブルー、焼成顔料、炭酸塩、リン酸塩、酢酸塩や、カーボンブラック、チタンブラック、アセチレンブラック、ランプブラック等を言い、有機顔料としては縮合アゾ系、ジスアゾ系、モノアゾ系、ジケトピロロピロール、イソインドリノン系、アンスラキノン系、複素環系、キナクリドン系、チオインジコ系、ペリノン系、ペリレン系、ジオキサジン系、フタロシアニン系等の顔料である。 The colorant used in the present invention is not particularly limited, and generally used inorganic pigments and organic pigments can be used. Examples of inorganic pigments include titanium dioxide, zinc white, lithopone, titanium yellow, white lead, red lead, yellow lead, heat-resistant yellow lead, complex oxide pigments, zinc sulfide, zinc oxide, barium sulfide, iron oxide, ultramarine, Bitumen, cobalt blue, calcined pigment, carbonate, phosphate, acetate, carbon black, titanium black, acetylene black, lamp black, etc. As organic pigments, condensed azo, disazo, monoazo, diketo Examples of the pigment include pyrrolopyrrole, isoindolinone, anthraquinone, heterocyclic, quinacridone, thioindico, perinone, perylene, dioxazine, and phthalocyanine.
着色剤の平均一次粒径としては、特に制限されないが、塗料の発色性から0.1〜10μmの範囲にあることが好ましい。上記平均一次粒子径が0.1μm未満であると光が散乱しにくくなるために、発色が低下するおそれがあり、好ましくない。10μmを超えると、塗料中での分散性が不充分となるため、多量に配合した場合の塗料の保存安定性が悪化するおそれがある。 The average primary particle size of the colorant is not particularly limited, but is preferably in the range of 0.1 to 10 μm from the color developability of the paint. If the average primary particle size is less than 0.1 μm, light is not easily scattered, and color development may be reduced, which is not preferable. If it exceeds 10 μm, the dispersibility in the paint becomes insufficient, so that the storage stability of the paint when blended in a large amount may be deteriorated.
着色剤の配合量は、ポリ乳酸樹脂100重量部に対して、0.1〜30重量部が好ましく、1〜20重量部がより好ましい。着色顔料の配合量がこの範囲であれば、昼間、夜間とも視認性が良好である。0.1重量部未満では着色性に乏しく、また30重量部を超えると塗料の流動性が低下するため施工性が悪化し、表面外観や塗膜密着強さが低下するため、好ましくない。 0.1-30 weight part is preferable with respect to 100 weight part of polylactic acid resin, and, as for the compounding quantity of a coloring agent, 1-20 weight part is more preferable. When the blending amount of the color pigment is within this range, the visibility is good both daytime and nighttime. If it is less than 0.1 parts by weight, the colorability is poor, and if it exceeds 30 parts by weight, the fluidity of the paint is lowered, so that the workability is deteriorated and the surface appearance and the adhesion strength of the coating film are lowered.
本発明で使用される反射材としては特に限定されないが、光を積極的に反射させるものとして、ガラスビーズや雲母片、アルミ粉やアルミフレーク等があり、主にガラスビーズが用いられる。ガラスビーズの粒径は、好ましくは0.1〜3mm、より好ましくは0.1〜2mmである。粒径がこの範囲であれば、視認性に優れる。ここでいう粒径とは、一般的に使用されているコールターカウンター法により、測定した値である。さらに、経日の視認性を向上させる目的でガラスカレット(粒径0.1〜3mm程度)を混合しても良い。 Although it does not specifically limit as a reflecting material used by this invention, As a thing which reflects light actively, there exist a glass bead, a mica piece, an aluminum powder, an aluminum flake, etc., and a glass bead is mainly used. The particle size of the glass beads is preferably 0.1 to 3 mm, more preferably 0.1 to 2 mm. If the particle size is within this range, the visibility is excellent. The particle diameter here is a value measured by a commonly used Coulter counter method. Furthermore, a glass cullet (particle size of about 0.1 to 3 mm) may be mixed for the purpose of improving the visibility of aging.
反射材の配合量は、ポリ乳酸樹脂100重量部に対して、好ましくは1〜50重量部、より好ましくは10〜40重量部である。配合量がこの範囲にあれば、施工し易く、夜間での視認性にも優れている。1重量部未満では夜間の視認性が低く、また50重量部を超えると塗料の流動性が低下するため施工性が悪化し、表面外観や塗膜密着強さが低下するため、好ましくない。 The amount of the reflective material is preferably 1 to 50 parts by weight, more preferably 10 to 40 parts by weight with respect to 100 parts by weight of the polylactic acid resin. If the blending amount is within this range, the construction is easy and the visibility at night is excellent. If it is less than 1 part by weight, the visibility at night is low, and if it exceeds 50 parts by weight, the fluidity of the paint is lowered, so that the workability is deteriorated, and the surface appearance and the adhesion strength of the coating film are lowered.
本発明の熱溶融型塗料組成物は、さらに充填剤を配合しても良い。本発明で使用する充填剤としては、珪酸鉱物、珪酸塩鉱物や種々の鉱物類を粉砕などの加工により微粉化したものが好ましく用いられる。具体例としては、ベントナイト、ドロマイト、バーライト、微粉ケイ酸、ケイ酸アルミニウム、酸化ケイ素、ドーソナイト、シラスバルーン、クレー、セリサイト、長石粉、ゼオライト(合成ゼオライトも含む)、滑石、マイカ、炭酸カルシウム、ガラスフレーク、ハイドロタルサイトおよびシリカなどが挙げられ、なかでも、炭酸カルシウムが好ましく使用できる。充填剤の平均粒子径は、表面外観、耐摩耗性の観点から、好ましくは100μm以下、より好ましくは50μm以下である。ここでいう平均粒子径とは、空気透過法による比表面積の測定結果から得た値である。 The hot melt coating composition of the present invention may further contain a filler. As the filler used in the present invention, a silicate mineral, a silicate mineral, and various minerals that are pulverized by processing such as pulverization are preferably used. Specific examples include bentonite, dolomite, barlite, fine silicate, aluminum silicate, silicon oxide, dosonite, shirasu balloon, clay, sericite, feldspar powder, zeolite (including synthetic zeolite), talc, mica, calcium carbonate , Glass flakes, hydrotalcite, silica and the like. Among them, calcium carbonate can be preferably used. The average particle diameter of the filler is preferably 100 μm or less, more preferably 50 μm or less, from the viewpoint of surface appearance and wear resistance. The average particle diameter here is a value obtained from the measurement result of the specific surface area by the air permeation method.
充填剤の配合量は、ポリ乳酸樹脂100重量部に対して、1〜200重量部であることが好ましい。200重量部を超えると、塗料組成物の流動性が低下し、施工性が悪化し、表面外観や塗膜密着強さが低下するため、好ましくない。 The blending amount of the filler is preferably 1 to 200 parts by weight with respect to 100 parts by weight of the polylactic acid resin. When the amount exceeds 200 parts by weight, the fluidity of the coating composition is lowered, the workability is deteriorated, and the surface appearance and the coating film adhesion strength are lowered.
本発明の熱溶融型塗料組成物は、さらに可塑剤を配合しても良い。本発明で使用する可塑剤としては、一般にポリマーの可塑剤として用いられる公知のものを特に制限なく用いることができ、例えばポリエステル系可塑剤、グリセリン系可塑剤、多価カルボン酸エステル系可塑剤、ポリアルキレングリコール系可塑剤、エポキシ系可塑剤、ネオペンチルグリコールジベンゾエート、ジエチレングリコールジベンゾエート、トリエチレングリコールジ−2−エチルブチレートなどの脂肪族ポリオールの安息香酸エステル、ステアリン酸アミドなどの脂肪酸アミド、オレイン酸ブチルなどの脂肪族カルボン酸エステル、アセチルリシノール酸メチル、アセチルリシノール酸ブチルなどのオキシ酸エステル、ペンタエリスリトール、ポリアクリル酸エステルおよびパラフィン類などを挙げることができる。
可塑剤の配合量は、ポリ乳酸樹脂100重量部に対して、0.1〜30重量部であることが好ましく、0.5〜25重量部であることがさらに好ましく、1〜20重量部であることが最も好ましい。可塑剤の配合量がこの範囲であれば施工し易く、低温時の可とう性、乾燥性および汚染性も良好である。0.1重量部未満では低温時の可とう性が低下し、30重量部を超えると可塑剤がブリードアウトを起こし、好ましくない。
The hot-melt coating composition of the present invention may further contain a plasticizer. As the plasticizer used in the present invention, known ones generally used as polymer plasticizers can be used without particular limitation, for example, polyester plasticizer, glycerin plasticizer, polyvalent carboxylic ester plasticizer, Polyalkylene glycol plasticizer, epoxy plasticizer, neopentyl glycol dibenzoate, diethylene glycol dibenzoate, benzoic acid ester of aliphatic polyol such as triethylene glycol di-2-ethylbutyrate, fatty acid amide such as stearamide, Examples include aliphatic carboxylic acid esters such as butyl oleate, oxyacid esters such as methyl acetylricinoleate and butyl acetylricinoleate, pentaerythritol, polyacrylic acid esters, and paraffins.
The blending amount of the plasticizer is preferably 0.1 to 30 parts by weight, more preferably 0.5 to 25 parts by weight, and 1 to 20 parts by weight with respect to 100 parts by weight of the polylactic acid resin. Most preferably it is. When the blending amount of the plasticizer is within this range, the construction is easy, and the flexibility at low temperatures, the drying property and the contamination property are also good. If it is less than 0.1 part by weight, the flexibility at low temperature is lowered, and if it exceeds 30 parts by weight, the plasticizer causes bleeding out, which is not preferable.
本発明の熱溶融型塗料組成物は、さらにカルボキシル基反応性末端封鎖剤を配合してもよい。カルボキシル基反応性末端封鎖剤としては、ポリマーのカルボキシル末端基を封鎖することのできる化合物であれば特に制限はなく、ポリマーのカルボキシル末端の封鎖剤として用いられているものを用いることができる。本発明においてかかるカルボキシル基反応性末端封鎖剤は、ポリ乳酸樹脂の末端を封鎖するのみではなく、ポリ乳酸樹脂の熱分解や加水分解などで生成する乳酸などの酸性低分子化合物のカルボキシル基を封鎖することができる。また、上記末端封鎖剤は、熱分解により酸性低分子化合物が生成する水酸基末端も封鎖できる化合物であることがさらに好ましい。 The hot-melt coating composition of the present invention may further contain a carboxyl group reactive end-capping agent. The carboxyl group-reactive terminal blocking agent is not particularly limited as long as it is a compound capable of blocking the carboxyl terminal group of the polymer, and those used as a blocking agent for the carboxyl terminal of the polymer can be used. In the present invention, the carboxyl group-reactive end-blocking agent not only blocks the end of the polylactic acid resin but also blocks the carboxyl group of acidic low-molecular compounds such as lactic acid produced by thermal decomposition or hydrolysis of the polylactic acid resin. can do. Further, the end-capping agent is more preferably a compound that can also block the hydroxyl end where an acidic low molecular weight compound is generated by thermal decomposition.
このようなカルボキシル基反応性末端封鎖剤としては、エポキシ化合物、オキサゾリン化合物、オキサジン化合物、カルボジイミド化合物から選ばれる少なくとも1種の化合物を使用することが好ましく、なかでもエポキシ化合物および/またはカルボジイミド化合物が好ましい。 As such a carboxyl group-reactive end-blocking agent, it is preferable to use at least one compound selected from an epoxy compound, an oxazoline compound, an oxazine compound, and a carbodiimide compound, and among them, an epoxy compound and / or a carbodiimide compound are preferable. .
本発明にカルボキシル基反応性末端封鎖剤として用いることのできるエポキシ化合物としては、グリシジルエーテル化合物、グリシジルエステル化合物、グリシジルアミン化合物、グリシジルイミド化合物、脂環式エポキシ化合物を好ましく使用することができる。これらを配合することで、耐久性に優れた熱溶融型塗料を得ることができる。 As an epoxy compound that can be used as a carboxyl group-reactive end-blocking agent in the present invention, a glycidyl ether compound, a glycidyl ester compound, a glycidyl amine compound, a glycidyl imide compound, and an alicyclic epoxy compound can be preferably used. By blending these, it is possible to obtain a hot-melt paint having excellent durability.
グリシジルエーテル化合物の例としては、ブチルグリシジルエーテル、ステアリルグリシジルエーテル、アリルグリシジルエーテル、フェニルグリシジルエーテル、o−フェニルフェニルグリシジルエーテル、エチレンオキシドラウリルアルコールグリシジルエーテル、エチレンオキシドフェノールグリシジルエーテル、エチレングリコールジグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテル、ポリテトラメチレングリコールジグリシジルエーテル、シクロヘキサンジメタノールジグリシジルエーテル、グリセロールトリグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、ペンタエリスリトールポリグリシジルエーテル、2,2−ビス−(4−ヒドロキシフェニル)プロパン、2,2−ビス−(4−ヒドロキシフェニル)メタン、ビス(4−ヒドロキシフェニル)スルホンなどのビスフェノール類とエピクロルヒドリンとの縮合反応から得られるビスフェノールAジグリシジルエーテル型エポキシ樹脂、ビスフェノールFジグリシジルエーテル型エポキシ樹脂、ビスフェノールSジグリシジルエーテル型エポキシ樹脂などを挙げることができる。なかでも、ビスフェノールAジグリシジルエーテル型エポキシ樹脂が好ましい。 Examples of glycidyl ether compounds include butyl glycidyl ether, stearyl glycidyl ether, allyl glycidyl ether, phenyl glycidyl ether, o-phenylphenyl glycidyl ether, ethylene oxide lauryl alcohol glycidyl ether, ethylene oxide phenol glycidyl ether, ethylene glycol diglycidyl ether, polyethylene glycol Diglycidyl ether, propylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, polytetramethylene glycol diglycidyl ether, cyclohexanedimethanol diglycidyl ether, glycerol triglycidyl ether, trimethylolpropane trig Bisphenols such as sidyl ether, pentaerythritol polyglycidyl ether, 2,2-bis- (4-hydroxyphenyl) propane, 2,2-bis- (4-hydroxyphenyl) methane, bis (4-hydroxyphenyl) sulfone; Examples thereof include a bisphenol A diglycidyl ether type epoxy resin, a bisphenol F diglycidyl ether type epoxy resin, a bisphenol S diglycidyl ether type epoxy resin obtained from a condensation reaction with epichlorohydrin. Among these, bisphenol A diglycidyl ether type epoxy resin is preferable.
グリシジルエステル化合物の例としては、安息香酸グリシジルエステル、p−トルイル酸グリシジルエステル、シクロヘキサンカルボン酸グリシジルエステル、ステアリン酸グリシジルエステル、ラウリン酸グリシジルエステル、パルミチン酸グリシジルエステル、バーサティック酸グリシジルエステル、オレイン酸グリシジルエステル、リノール酸グリシジルエステル、リノレン酸グリシジルエステル、テレフタル酸ジグリシジルエステル、イソフタル酸ジグリシジルエステル、フタル酸ジグリシジルエステル、ナフタレンジカルボン酸ジグリシジルエステル、ビ安息香酸ジグリシジルエステル、メチルテレフタル酸ジグリシジルエステル、ヘキサヒドロフタル酸ジグリシジルエステル、テトラヒドロフタル酸ジグリシジルエステル、シクロヘキサンジカルボン酸ジグリシジルエステル、アジピン酸ジグリシジルエステル、コハク酸ジグリシジルエステル、セバシン酸ジグリシジルエステル、ドデカンジオン酸ジグリシジルエステル、オクタデカンジカルボン酸ジグリシジルエステル、トリメリット酸トリグリシジルエステル、ピロメリット酸テトラグリシジルエステルなどのを挙げることができる。なかでも、安息香酸グリシジルエステルやバーサティック酸グリシジルエステルが好ましい。 Examples of glycidyl ester compounds include benzoic acid glycidyl ester, p-toluic acid glycidyl ester, cyclohexanecarboxylic acid glycidyl ester, stearic acid glycidyl ester, lauric acid glycidyl ester, palmitic acid glycidyl ester, versatic acid glycidyl ester, oleic acid glycidyl ester Ester, linoleic acid glycidyl ester, linolenic acid glycidyl ester, terephthalic acid diglycidyl ester, isophthalic acid diglycidyl ester, phthalic acid diglycidyl ester, naphthalene dicarboxylic acid diglycidyl ester, bibenzoic acid diglycidyl ester, methyl terephthalic acid diglycidyl ester , Hexahydrophthalic acid diglycidyl ester, tetrahydrophthalic acid diglycidyl ester, Hexanedicarboxylic acid diglycidyl ester, adipic acid diglycidyl ester, succinic acid diglycidyl ester, sebacic acid diglycidyl ester, dodecanedioic acid diglycidyl ester, octadecanedicarboxylic acid diglycidyl ester, trimellitic acid triglycidyl ester, pyromellitic acid tetra A glycidyl ester etc. can be mentioned. Among these, benzoic acid glycidyl ester and versatic acid glycidyl ester are preferable.
グリシジルアミン化合物の例としては、テトラグリシジルアミノジフェニルメタン、トリグリシジル−パラアミノフェノール、トリグリシジル−メタアミノフェノール、ジグリシジルアニリン、ジグリシジルトルイジン、テトラグリシジルメタキシレンジアミン、ジグリシジルトリブロモアニリン、テトラグリシジルビスアミノメチルシクロヘキサン、トリグリシジルシアヌレート、トリグリシジルイソシアヌレートなどを挙げることができる。グリシジルイミド化合物の例としては、N−グリシジルフタルイミド、N−グリシジル−4−メチルフタルイミド、N−グリシジル−4,5−ジメチルフタルイミド、N−グリシジル−3−メチルフタルイミド、N−グリシジル−3,6−ジメチルフタルイミド、N−グリシジル−4−エトキシフタルイミド、N−グリシジル−4−クロルフタルイミド、N−グリシジル−4,5−ジクロルフタルイミド、N−グリシジル−3,4,5,6−テトラブロムフタルイミド、N−グリシジル−4−n−ブチル−5−ブロムフタルイミド、N−グリシジルサクシンイミド、N−グリシジルヘキサヒドロフタルイミド、N−グリシジル−1,2,3,6−テトラヒドロフタルイミド、N−グリシジルマレインイミド、N−グリシジル−α,β−ジメチルサクシンイミド、N−グリシジル−α−エチルサクシンイミド、N−グリシジル−α−プロピルサクシンイミド、N−グリシジルベンズアミド、N−グリシジル−p−メチルベンズアミド、N−グリシジルナフトアミド、N−グリシジルステラミドなどを挙げることができる。なかでも、N−グリシジルフタルイミドが好ましい。 Examples of glycidylamine compounds include tetraglycidylaminodiphenylmethane, triglycidyl-paraaminophenol, triglycidyl-metaaminophenol, diglycidylaniline, diglycidyltoluidine, tetraglycidylmetaxylenediamine, diglycidyltribromoaniline, tetraglycidylbisamino Examples include methylcyclohexane, triglycidyl cyanurate, and triglycidyl isocyanurate. Examples of glycidylimide compounds include N-glycidylphthalimide, N-glycidyl-4-methylphthalimide, N-glycidyl-4,5-dimethylphthalimide, N-glycidyl-3-methylphthalimide, N-glycidyl-3,6- Dimethylphthalimide, N-glycidyl-4-ethoxyphthalimide, N-glycidyl-4-chlorophthalimide, N-glycidyl-4,5-dichlorophthalimide, N-glycidyl-3,4,5,6-tetrabromophthalimide, N -Glycidyl-4-n-butyl-5-bromophthalimide, N-glycidyl succinimide, N-glycidyl hexahydrophthalimide, N-glycidyl-1,2,3,6-tetrahydrophthalimide, N-glycidyl maleimide, N- Glycidyl-α, β-dimethyl Succinimide, N-glycidyl-α-ethylsuccinimide, N-glycidyl-α-propylsuccinimide, N-glycidylbenzamide, N-glycidyl-p-methylbenzamide, N-glycidylnaphthamide, N-glycidylsteramide, etc. be able to. Of these, N-glycidylphthalimide is preferable.
脂環式エポキシ化合物の例としては、3,4−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキシルカルボキシレート、ビス(3,4−エポキシシクロヘキシルメチル)アジペート、ビニルシクロヘキセンジエポキシド、N−メチル−4,5−エポキシシクロヘキサン−1,2−ジカルボン酸イミド、N−エチル−4,5−エポキシシクロヘキサン−1,2−ジカルボン酸イミド、N−フェニル−4,5−エポキシシクロヘキサン−1,2−ジカルボン酸イミド、N−ナフチル−4,5−エポキシシクロヘキサン−1,2−ジカルボン酸イミド、N−トリル−3−メチル−4,5−エポキシシクロヘキサン−1,2−ジカルボン酸イミドなどを挙げることができる。 Examples of alicyclic epoxy compounds include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexylcarboxylate, bis (3,4-epoxycyclohexylmethyl) adipate, vinylcyclohexene diepoxide, N-methyl-4, 5-epoxycyclohexane-1,2-dicarboxylic imide, N-ethyl-4,5-epoxycyclohexane-1,2-dicarboxylic imide, N-phenyl-4,5-epoxycyclohexane-1,2-dicarboxylic imide N-naphthyl-4,5-epoxycyclohexane-1,2-dicarboxylic imide, N-tolyl-3-methyl-4,5-epoxycyclohexane-1,2-dicarboxylic imide, and the like.
また、その他のエポキシ化合物として、エポキシ化大豆油、エポキシ化アマニ油、エポキシ化鯨油などのエポキシ変性脂肪酸グリセリド、フェノールノボラック型エポキシ樹脂、クレゾールノゾラック型エポキシ樹脂などを用いることができる。 Further, as other epoxy compounds, epoxy-modified fatty acid glycerides such as epoxidized soybean oil, epoxidized linseed oil, and epoxidized whale oil, phenol novolac type epoxy resins, cresol nozolac type epoxy resins, and the like can be used.
本発明で用いるカルボキシル基反応性末端封鎖剤として用いることのできるオキサゾリン化合物の例としては、2−メトキシ−2−オキサゾリン、2−エトキシ−2−オキサゾリン、2−プロポキシ−2−オキサゾリン、2−ブトキシ−2−オキサゾリン、2−ペンチルオキシ−2−オキサゾリン、2−ヘキシルオキシ−2−オキサゾリン、2−ヘプチルオキシ−2−オキサゾリン、2−オクチルオキシ−2−オキサゾリン、2−ノニルオキシ−2−オキサゾリン、2−デシルオキシ−2−オキサゾリン、2−シクロペンチルオキシ−2−オキサゾリン、2−シクロヘキシルオキシ−2−オキサゾリン、2−アリルオキシ−2−オキサゾリン、2−メタアリルオキシ−2−オキサゾリン、2−クロチルオキシ−2−オキサゾリン、2−フェノキシ−2−オキサゾリン、2−クレジル−2−オキサゾリン、2−o−エチルフェノキシ−2−オキサゾリン、2−o−プロピルフェノキシ−2−オキサゾリン、2−o−フェニルフェノキシ−2−オキサゾリン、2−m−エチルフェノキシ−2−オキサゾリン、2−m−プロピルフェノキシ−2−オキサゾリン、2−p−フェニルフェノキシ−2−オキサゾリン、2−メチル−2−オキサゾリン、2−エチル−2−オキサゾリン、2−プロピル−2−オキサゾリン、2−ブチル−2−オキサゾリン、2−ペンチル−2−オキサゾリン、2−ヘキシル−2−オキサゾリン、2−ヘプチル−2−オキサゾリン、2−オクチル−2−オキサゾリン、2−ノニル−2−オキサゾリン、2−デシル−2−オキサゾリン、2−シクロペンチル−2−オキサゾリン、2−シクロヘキシル−2−オキサゾリン、2−アリル−2−オキサゾリン、2−メタアリル−2−オキサゾリン、2−クロチル−2−オキサゾリン、2−フェニル−2−オキサゾリン、2−o−エチルフェニル−2−オキサゾリン、2−o−プロピルフェニル−2−オキサゾリン、2−o−フェニルフェニル−2−オキサゾリン、2−m−エチルフェニル−2−オキサゾリン、2−m−プロピルフェニル−2−オキサゾリン、2−p−フェニルフェニル−2−オキサゾリン、2,2′−ビス(2−オキサゾリン)、2,2′−ビス(4−メチル−2−オキサゾリン)、2,2′−ビス(4,4′−ジメチル−2−オキサゾリン)、2,2′−ビス(4−エチル−2−オキサゾリン)、2,2′−ビス(4,4′−ジエチル−2−オキサゾリン)、2,2′−ビス(4−プロピル−2−オキサゾリン)、2,2′−ビス(4−ブチル−2−オキサゾリン)、2,2′−ビス(4−ヘキシル−2−オキサゾリン)、2,2′−ビス(4−フェニル−2−オキサゾリン)、2,2′−ビス(4−シクロヘキシル−2−オキサゾリン)、2,2′−ビス(4−ベンジル−2−オキサゾリン)、2,2′−p−フェニレンビス(2−オキサゾリン)、2,2′−m−フェニレンビス(2−オキサゾリン)、2,2′−o−フェニレンビス(2−オキサゾリン)、2,2′−p−フェニレンビス(4−メチル−2−オキサゾリン)、2,2′−p−フェニレンビス(4,4′−ジメチル−2−オキサゾリン)、2,2′−m−フェニレンビス(4−メチル−2−オキサゾリン)、2,2′−m−フェニレンビス(4,4′−ジメチル−2−オキサゾリン)、2,2′−エチレンビス(2−オキサゾリン)、2,2′−テトラメチレンビス(2−オキサゾリン)、2,2′−ヘキサメチレンビス(2−オキサゾリン)、2,2′−オクタメチレンビス(2−オキサゾリン)、2,2′−デカメチレンビス(2−オキサゾリン)、2,2′−エチレンビス(4−メチル−2−オキサゾリン)、2,2′−テトラメチレンビス(4,4′−ジメチル−2−オキサゾリン)、2,2′−9,9′−ジフェノキシエタンビス(2−オキサゾリン)、2,2′−シクロヘキシレンビス(2−オキサゾリン)、2,2′−ジフェニレンビス(2−オキサゾリン)などが挙げられる。さらには、上記した化合物をモノマー単位として含むポリオキサゾリン化合物なども挙げることができる。 Examples of the oxazoline compound that can be used as a carboxyl group-reactive end-blocking agent used in the present invention include 2-methoxy-2-oxazoline, 2-ethoxy-2-oxazoline, 2-propoxy-2-oxazoline, 2-butoxy 2-oxazoline, 2-pentyloxy-2-oxazoline, 2-hexyloxy-2-oxazoline, 2-heptyloxy-2-oxazoline, 2-octyloxy-2-oxazoline, 2-nonyloxy-2-oxazoline, 2 -Decyloxy-2-oxazoline, 2-cyclopentyloxy-2-oxazoline, 2-cyclohexyloxy-2-oxazoline, 2-allyloxy-2-oxazoline, 2-methallyloxy-2-oxazoline, 2-crotyloxy-2-oxazoline , 2-pheno Ci-2-oxazoline, 2-cresyl-2-oxazoline, 2-o-ethylphenoxy-2-oxazoline, 2-o-propylphenoxy-2-oxazoline, 2-o-phenylphenoxy-2-oxazoline, 2-m -Ethylphenoxy-2-oxazoline, 2-m-propylphenoxy-2-oxazoline, 2-p-phenylphenoxy-2-oxazoline, 2-methyl-2-oxazoline, 2-ethyl-2-oxazoline, 2-propyl- 2-oxazoline, 2-butyl-2-oxazoline, 2-pentyl-2-oxazoline, 2-hexyl-2-oxazoline, 2-heptyl-2-oxazoline, 2-octyl-2-oxazoline, 2-nonyl-2- Oxazoline, 2-decyl-2-oxazoline, 2-cyclopentyl-2-oxy Zolin, 2-cyclohexyl-2-oxazoline, 2-allyl-2-oxazoline, 2-methallyl-2-oxazoline, 2-crotyl-2-oxazoline, 2-phenyl-2-oxazoline, 2-o-ethylphenyl-2 -Oxazoline, 2-o-propylphenyl-2-oxazoline, 2-o-phenylphenyl-2-oxazoline, 2-m-ethylphenyl-2-oxazoline, 2-m-propylphenyl-2-oxazoline, 2-p -Phenylphenyl-2-oxazoline, 2,2'-bis (2-oxazoline), 2,2'-bis (4-methyl-2-oxazoline), 2,2'-bis (4,4'-dimethyl- 2-oxazoline), 2,2'-bis (4-ethyl-2-oxazoline), 2,2'-bis (4,4'-diethyl-2-oxy) Sazoline), 2,2'-bis (4-propyl-2-oxazoline), 2,2'-bis (4-butyl-2-oxazoline), 2,2'-bis (4-hexyl-2-oxazoline) 2,2'-bis (4-phenyl-2-oxazoline), 2,2'-bis (4-cyclohexyl-2-oxazoline), 2,2'-bis (4-benzyl-2-oxazoline), 2 , 2'-p-phenylenebis (2-oxazoline), 2,2'-m-phenylenebis (2-oxazoline), 2,2'-o-phenylenebis (2-oxazoline), 2,2'-p -Phenylenebis (4-methyl-2-oxazoline), 2,2'-p-phenylenebis (4,4'-dimethyl-2-oxazoline), 2,2'-m-phenylenebis (4-methyl-2) -Oxazoline), 2, 2 -M-phenylenebis (4,4'-dimethyl-2-oxazoline), 2,2'-ethylenebis (2-oxazoline), 2,2'-tetramethylenebis (2-oxazoline), 2,2'- Hexamethylene bis (2-oxazoline), 2,2'-octamethylene bis (2-oxazoline), 2,2'-decamethylene bis (2-oxazoline), 2,2'-ethylenebis (4-methyl-2) -Oxazoline), 2,2'-tetramethylenebis (4,4'-dimethyl-2-oxazoline), 2,2'-9,9'-diphenoxyethanebis (2-oxazoline), 2,2'- Examples include cyclohexylenebis (2-oxazoline), 2,2'-diphenylenebis (2-oxazoline), and the like. Furthermore, the polyoxazoline compound etc. which contain the above-mentioned compound as a monomer unit can be mentioned.
本発明で用いることのできるカルボキシル基反応性末端封鎖剤としてのオキサジン化合物の例としては、2−メトキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−エトキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−プロポキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−ブトキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−ペンチルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−ヘキシルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−ヘプチルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−オクチルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−ノニルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−デシルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−シクロペンチルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−シクロヘキシルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−アリルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−メタアリルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−クロチルオキシ−5,6−ジヒドロ−4H−1,3−オキサジンなどが挙げられ、さらには、2,2′−ビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2′−メチレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2′−エチレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2′−プロピレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2′−ブチレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2′−ヘキサメチレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2′−p−フェニレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2′−m−フェニレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2′−ナフチレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2′−P,P′−ジフェニレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)などが挙げられる。さらには、上記した化合物をモノマー単位として含むポリオキサジン化合物などが挙げられる。 Examples of oxazine compounds as carboxyl group-reactive endblockers that can be used in the present invention include 2-methoxy-5,6-dihydro-4H-1,3-oxazine, 2-ethoxy-5,6-dihydro. -4H-1,3-oxazine, 2-propoxy-5,6-dihydro-4H-1,3-oxazine, 2-butoxy-5,6-dihydro-4H-1,3-oxazine, 2-pentyloxy- 5,6-dihydro-4H-1,3-oxazine, 2-hexyloxy-5,6-dihydro-4H-1,3-oxazine, 2-heptyloxy-5,6-dihydro-4H-1,3- Oxazine, 2-octyloxy-5,6-dihydro-4H-1,3-oxazine, 2-nonyloxy-5,6-dihydro-4H-1,3-oxazine, 2-decyloxy-5 6-dihydro-4H-1,3-oxazine, 2-cyclopentyloxy-5,6-dihydro-4H-1,3-oxazine, 2-cyclohexyloxy-5,6-dihydro-4H-1,3-oxazine, 2-allyloxy-5,6-dihydro-4H-1,3-oxazine, 2-methallyloxy-5,6-dihydro-4H-1,3-oxazine, 2-crotyloxy-5,6-dihydro-4H- 1,3-oxazine and the like, and further, 2,2′-bis (5,6-dihydro-4H-1,3-oxazine), 2,2′-methylenebis (5,6-dihydro-4H— 1,3-oxazine), 2,2'-ethylenebis (5,6-dihydro-4H-1,3-oxazine), 2,2'-propylenebis (5,6-dihydro-4H-1,3- Oxazi ), 2,2'-butylenebis (5,6-dihydro-4H-1,3-oxazine), 2,2'-hexamethylenebis (5,6-dihydro-4H-1,3-oxazine), 2, 2'-p-phenylenebis (5,6-dihydro-4H-1,3-oxazine), 2,2'-m-phenylenebis (5,6-dihydro-4H-1,3-oxazine), 2, 2'-naphthylene bis (5,6-dihydro-4H-1,3-oxazine), 2,2'-P, P'-diphenylene bis (5,6-dihydro-4H-1,3-oxazine), etc. Can be mentioned. Furthermore, the polyoxazine compound etc. which contain an above-described compound as a monomer unit are mentioned.
上記オキサゾリン合物やオキサジン化合物の中では、2,2′−m−フェニレンビス(2−オキサゾリン)、2,2′−p−フェニレンビス(2−オキサゾリン)が好ましい。 Among the oxazoline compounds and oxazine compounds, 2,2′-m-phenylenebis (2-oxazoline) and 2,2′-p-phenylenebis (2-oxazoline) are preferable.
本発明でカルボキシル基反応性末端封鎖剤として使用することのできるカルボジイミド化合物とは、分子内に少なくともひとつの(−N=C=N−)で表されるカルボジイミド基を有する化合物であり、例えば適当な触媒の存在下に、有機イソシアネートを加熱し、脱炭酸反応で製造できる。 The carbodiimide compound that can be used as a carboxyl group-reactive end-blocking agent in the present invention is a compound having at least one carbodiimide group represented by (—N═C═N—) in the molecule. The organic isocyanate can be heated in the presence of a simple catalyst and produced by decarboxylation.
カルボジイミド化合物の例としては、ジフェニルカルボジイミド、ジ−シクロヘキシルカルボジイミド、ジ−2,6−ジメチルフェニルカルボジイミド、ジイソプロピルカルボジイミド、ジオクチルデシルカルボジイミド、ジ−o−トルイルカルボジイミド、ジ−p−トルイルカルボジイミド、ジ−p−ニトロフェニルカルボジイミド、ジ−p−アミノフェニルカルボジイミド、ジ−p−ヒドロキシフェニルカルボジイミド、ジ−p−クロルフェニルカルボジイミド、ジ−o−クロルフェニルカルボジイミド、ジ−3,4−ジクロルフェニルカルボジイミド、ジ−2,5−ジクロルフェニルカルボジイミド、p−フェニレン−ビス−o−トルイルカルボジイミド、p−フェニレン−ビス−ジシクロヘキシルカルボジイミド、p−フェニレン−ビス−ジ−p−クロルフェニルカルボジイミド、2,6,2′,6′−テトライソプロピルジフェニルカルボジイミド、ヘキサメチレン−ビス−シクロヘキシルカルボジイミド、エチレン−ビス−ジフェニルカルボジイミド、エチレン−ビス−ジ−シクロヘキシルカルボジイミド、N,N′−ジ−o−トリイルカルボジイミド、N,N′−ジフェニルカルボジイミド、N,N′−ジオクチルデシルカルボジイミド、N,N′−ジ−2,6−ジメチルフェニルカルボジイミド、N−トリイル−N′−シクロヘキシルカルボジイミド、N,N′−ジ−2,6−ジイソプロピルフェニルカルボジイミド、N,N′−ジ−2,6−ジ−tert−ブチルフェニルカルボジイミド、N−トルイル−N′−フェニルカルボジイミド、N,N′−ジ−p−ニトロフェニルカルボジイミド、N,N′−ジ−p−アミノフェニルカルボジイミド、N,N′−ジ−p−ヒドロキシフェニルカルボジイミド、N,N′−ジ−シクロヘキシルカルボジイミド、N,N′−ジ−p−トルイルカルボジイミド、N,N′−ベンジルカルボジイミド、N−オクタデシル−N′−フェニルカルボジイミド、N−ベンジル−N′−フェニルカルボジイミド、N−オクタデシル−N′−トリルカルボジイミド、N−シクロヘキシル−N′−トリルカルボジイミド、N−フェニル−N′−トリルカルボジイミド、N−ベンジル−N′−トリルカルボジイミド、N,N′−ジ−o−エチルフェニルカルボジイミド、N,N′−ジ−p−エチルフェニルカルボジイミド、N,N′−ジ−o−イソプロピルフェニルカルボジイミド、N,N′−ジ−p−イソプロピルフェニルカルボジイミド、N,N′−ジ−o−イソブチルフェニルカルボジイミド、N,N′−ジ−p−イソブチルフェニルカルボジイミド、N,N′−ジ−2,6−ジエチルフェニルカルボジイミド、N,N′−ジ−2−エチル−6−イソプロピルフェニルカルボジイミド、N,N′−ジ−2−イソブチル−6−イソプロピルフェニルカルボジイミド、N,N′−ジ−2,4,6−トリメチルフェニルカルボジイミド、N,N′−ジ−2,4,6−トリイソプロピルフェニルカルボジイミド、N,N′−ジ−2,4,6−トリイソブチルフェニルカルボジイミドなどのモノ又はジカルボジイミド化合物、ポリ(1,6−ヘキサメチレンカルボジイミド)、ポリ(4,4′−メチレンビスシクロヘキシルカルボジイミド)、ポリ(1,3−シクロヘキシレンカルボジイミド)、ポリ(1,4−シクロヘキシレンカルボジイミド)、ポリ(4,4′−ジフェニルメタンカルボジイミド)、ポリ(3,3′−ジメチル−4,4′−ジフェニルメタンカルボジイミド)、ポリ(ナフチレンカルボジイミド)、ポリ(p−フェニレンカルボジイミド)、ポリ(m−フェニレンカルボジイミド)、ポリ(トリルカルボジイミド)、ポリ(ジイソプロピルカルボジイミド)、ポリ(メチル−ジイソプロピルフェニレンカルボジイミド)、ポリ(トリエチルフェニレンカルボジイミド)、ポリ(トリイソプロピルフェニレンカルボジイミド)などのポリカルボジイミドなどが挙げられる。なかでもN,N′−ジ−2,6−ジイソプロピルフェニルカルボジイミド、2,6,2′,6′−テトライソプロピルジフェニルカルボジイミドが好ましい。 Examples of carbodiimide compounds include diphenylcarbodiimide, di-cyclohexylcarbodiimide, di-2,6-dimethylphenylcarbodiimide, diisopropylcarbodiimide, dioctyldecylcarbodiimide, di-o-toluylcarbodiimide, di-p-toluylcarbodiimide, di-p- Nitrophenylcarbodiimide, di-p-aminophenylcarbodiimide, di-p-hydroxyphenylcarbodiimide, di-p-chlorophenylcarbodiimide, di-o-chlorophenylcarbodiimide, di-3,4-dichlorophenylcarbodiimide, di-2 , 5-dichlorophenylcarbodiimide, p-phenylene-bis-o-toluylcarbodiimide, p-phenylene-bis-dicyclohexylcarbodiimide, p-phenylene- Su-di-p-chlorophenylcarbodiimide, 2,6,2 ', 6'-tetraisopropyldiphenylcarbodiimide, hexamethylene-bis-cyclohexylcarbodiimide, ethylene-bis-diphenylcarbodiimide, ethylene-bis-dicyclohexylcarbodiimide, N , N′-di-o-triylcarbodiimide, N, N′-diphenylcarbodiimide, N, N′-dioctyldecylcarbodiimide, N, N′-di-2,6-dimethylphenylcarbodiimide, N-triyl-N ′ -Cyclohexylcarbodiimide, N, N'-di-2,6-diisopropylphenylcarbodiimide, N, N'-di-2,6-di-tert-butylphenylcarbodiimide, N-toluyl-N'-phenylcarbodiimide, N, N'-di-p-ni Rophenylcarbodiimide, N, N'-di-p-aminophenylcarbodiimide, N, N'-di-p-hydroxyphenylcarbodiimide, N, N'-di-cyclohexylcarbodiimide, N, N'-di-p-toluyl Carbodiimide, N, N′-benzylcarbodiimide, N-octadecyl-N′-phenylcarbodiimide, N-benzyl-N′-phenylcarbodiimide, N-octadecyl-N′-tolylcarbodiimide, N-cyclohexyl-N′-tolylcarbodiimide, N-phenyl-N'-tolylcarbodiimide, N-benzyl-N'-tolylcarbodiimide, N, N'-di-o-ethylphenylcarbodiimide, N, N'-di-p-ethylphenylcarbodiimide, N, N ' -Di-o-isopropylphenylcarbodiimide, N, N'-di-p-isopropylphenylcarbodiimide, N, N'-di-o-isobutylphenylcarbodiimide, N, N'-di-p-isobutylphenylcarbodiimide, N, N'-di-2,6- Diethylphenylcarbodiimide, N, N'-di-2-ethyl-6-isopropylphenylcarbodiimide, N, N'-di-2-isobutyl-6-isopropylphenylcarbodiimide, N, N'-di-2,4,6 Mono- or dicarbodiimide compounds such as trimethylphenylcarbodiimide, N, N′-di-2,4,6-triisopropylphenylcarbodiimide, N, N′-di-2,4,6-triisobutylphenylcarbodiimide, poly ( 1,6-hexamethylenecarbodiimide), poly (4,4'-methylenebiscyclohexylcal) Diimide), poly (1,3-cyclohexylenecarbodiimide), poly (1,4-cyclohexylenecarbodiimide), poly (4,4'-diphenylmethanecarbodiimide), poly (3,3'-dimethyl-4,4'- Diphenylmethanecarbodiimide), poly (naphthylenecarbodiimide), poly (p-phenylenecarbodiimide), poly (m-phenylenecarbodiimide), poly (tolylcarbodiimide), poly (diisopropylcarbodiimide), poly (methyl-diisopropylphenylenecarbodiimide), poly ( And polycarbodiimides such as triethylphenylenecarbodiimide) and poly (triisopropylphenylenecarbodiimide). Of these, N, N′-di-2,6-diisopropylphenylcarbodiimide and 2,6,2 ′, 6′-tetraisopropyldiphenylcarbodiimide are preferable.
上記カルボキシル基反応性末端封鎖剤は1種または2種以上の化合物を任意に選択して使用することができる。 As the carboxyl group-reactive end-blocking agent, one or more compounds can be arbitrarily selected and used.
カルボキシル基反応性末端封鎖剤の量は、ポリ乳酸樹脂100重量部としたときに、0.01〜10重量部が好ましく、0.05〜5重量部がさらに好ましい。 The amount of the carboxyl group-reactive end-blocking agent is preferably 0.01 to 10 parts by weight, more preferably 0.05 to 5 parts by weight, based on 100 parts by weight of the polylactic acid resin.
また、本発明の熱溶融型塗料組成物に対して、本発明の目的を損なわない範囲で、ポリ乳酸樹脂以外の粘結樹脂、無機繊維、有機繊維、蓄光顔料、蛍光顔料、夜光顔料、沈降防止剤、流動性改良剤、老化防止剤、紫外線吸収剤などを配合してもよい。ポリ乳酸樹脂以外の粘結樹脂としては、例えば、生ロジン、マレイン化ロジン、マレイン化ロジンエステル樹脂、水添ロジン、石油樹脂、水添石油樹脂、テルペン樹脂などが挙げられる。 Further, for the hot-melt coating composition of the present invention, a caking resin other than polylactic acid resin, inorganic fibers, organic fibers, phosphorescent pigments, fluorescent pigments, nocturnal pigments, sedimentation, as long as the object of the present invention is not impaired. You may mix | blend an inhibitor, a fluid improvement agent, anti-aging agent, a ultraviolet absorber, etc. Examples of the binder resin other than the polylactic acid resin include raw rosin, maleated rosin, maleated rosin ester resin, hydrogenated rosin, petroleum resin, hydrogenated petroleum resin, and terpene resin.
以上の塗料組成物を構成する各成分を乾式混合することにより、熱溶融型塗料組成物が製造できる。本発明において、乾式混合するとは、配合された熱溶融型塗料組成物が溶融しない条件で、各成分を混合することをいう。 A hot-melt coating composition can be produced by dry-mixing the components constituting the coating composition. In the present invention, dry mixing means mixing the components under the condition that the blended hot-melt coating composition does not melt.
乾式混合の方法としては、例えば、タンブラーミキサーやヘンシェルミキサーなどで混合する方法が挙げられる。 Examples of the dry mixing method include a method of mixing with a tumbler mixer or a Henschel mixer.
得られた熱溶融型塗料組成物は、ポリエチレン製や紙製の袋に所定量詰めることにより、運搬し易くなる。 The obtained hot-melt coating composition is easily transported by packing a predetermined amount in a polyethylene or paper bag.
本発明の熱溶融型道路標示塗料組成物は、前記の方法で得られるものである。 The hot melt type road marking paint composition of the present invention is obtained by the above method.
この熱溶融型塗料組成物は、通常、加熱ニーダーなどの加熱溶融混練装置を用いて、170〜210℃で溶融混練される。溶融物を道路表面に塗布する場合は、平滑表示・区画線用施工機を用いて、溶融状態で道路上に施工される。施工にあたり、予め道路表面に下地処理を施すこともできる。 This hot-melt coating composition is usually melt-kneaded at 170-210 ° C. using a heat-melt kneader such as a heat kneader. When the melt is applied to the road surface, the melt is applied on the road in a molten state using a smooth display / division line construction machine. In construction, the surface of the road can be pretreated.
以下に、実施例によって本発明を更に詳細に説明するが、これらは本発明を限定するものではない。また、使用した原料を以下に示す。
(A)粘結樹脂
(A−1)ポリ乳酸樹脂:L/D=95/5、重量平均分子量5万
(A−2)ポリ乳酸樹脂:L/D=5/95、重量平均分子量5万
(A−3)ポリ乳酸樹脂:L/D=99.5/0.5、重量平均分子量5万
(A−4)ポリ乳酸樹脂:L/D=95/5、重量平均分子量15万
(A−5)石油樹脂:C5系石油樹脂(丸善石油化学)
(B)着色剤:二酸化チタン(石原産業「タイペークCR−60」)
(C)反射剤:ガラスビーズ(ポッターズ・バロティーニ「GB153T」、粒径範囲:0.11〜0.85mm)
(D)充填材:重質炭酸カルシウム(白石カルシウム「BF−200」、平均粒子径5μm)
(E)可塑剤:ポリエチレングリコール(三洋化成「PEG−6000P」)
(F)カルボキシル基反応性末端封鎖剤
(F−1)ポリカルボジイミド化合物(日清紡績“カルボジライト”HMV−8CA)
(F−2)エポキシ基含有スチレン/アクリル酸エステル共重合体(東亞合成“ARUFON”UG4040)
The present invention will be described in more detail below by way of examples, but these examples do not limit the present invention. Moreover, the used raw material is shown below.
(A) Binder resin (A-1) Polylactic acid resin: L / D = 95/5, weight average molecular weight 50,000 (A-2) Polylactic acid resin: L / D = 5/95, weight average molecular weight 50,000 (A-3) Polylactic acid resin: L / D = 99.5 / 0.5, weight average molecular weight 50,000 (A-4) Polylactic acid resin: L / D = 95/5, weight average molecular weight 150,000 (A -5) Petroleum resin: C5 petroleum resin (Maruzen Petrochemical)
(B) Colorant: Titanium dioxide (Ishihara Sangyo “Taipeke CR-60”)
(C) Reflector: Glass beads (Potters Ballotini “GB153T”, particle size range: 0.11 to 0.85 mm)
(D) Filler: Heavy calcium carbonate (Shiraishi calcium “BF-200”, average particle size 5 μm)
(E) Plasticizer: Polyethylene glycol (Sanyo Kasei “PEG-6000P”)
(F) Carboxyl group reactive end-capping agent (F-1) Polycarbodiimide compound (Nisshinbo "Carbodilite" HMV-8CA)
(F-2) Epoxy group-containing styrene / acrylic acid ester copolymer (Toagosei "ARUFON" UG4040)
また、本発明の実施例および比較例で用いた測定方法および評価方法を以下に示す。 The measurement methods and evaluation methods used in the examples and comparative examples of the present invention are shown below.
(1)環境負荷
粘結樹脂にバイオマス樹脂を使用した場合を○、石油系樹脂を使用した場合を×とした。
(1) Environmental load The case where a biomass resin was used for the caking resin was marked with ◯, and the case where a petroleum resin was used was marked with ×.
(2)表面状態
乾式混合した熱溶融型塗料組成物を、ニーダー混合機を用いて、190℃にて30分間混練した。30分間混練した溶融物の表面状態を観察して、以下の基準で判定した。
○:表面に艶があり、平滑である
×:表面に艶がなく、ざらついている。
(2) Surface condition The dry-mixed hot-melt coating composition was kneaded at 190 ° C. for 30 minutes using a kneader mixer. The surface condition of the melt kneaded for 30 minutes was observed and judged according to the following criteria.
○: The surface is glossy and smooth. ×: The surface is not glossy and rough.
(3)施工性
熱溶融型塗料を190℃で加熱溶融させ、施工速度0.8km/hにてかすれ等の不具合が生じないかを目視観察した。
◎:塗料の伸びが非常に良好であり、かすれ無し
○:塗料の伸びが良好であり、かすれ無し
△:塗料の伸びがやや悪く、かすれもやや確認できる
×:塗料の伸びが悪く、かすれが大きい。
(3) Workability The hot-melt paint was heated and melted at 190 ° C. and visually observed for defects such as fading at a construction speed of 0.8 km / h.
◎: Elongation of paint is very good, no blurring ○: Elongation of paint is good, no blurring △: Elongation of paint is slightly worse, faintness can be confirmed slightly ×: Poor elongation of paint is poor, blurring large.
(4)密着強さ
コンクリート平板上に熱溶融型塗料を190℃で塗布し、23℃で24時間放置後、インストロン製5581型引張試験機を用いて、速度5mm/minで引張試験を行い、剥離までの最大荷重を測定した。
(5)耐久性
コンクリート平板上に190℃で塗布したものを12ヶ月間屋外暴露し、塗料の状態に異常がないか目視観察した。
○:異常なし
△:やや気泡が発生するが、塗料の崩壊なし
×:塗料が崩壊
(4) Adhesion strength After applying a hot melt paint at 190 ° C on a concrete flat plate and leaving it at 23 ° C for 24 hours, a tensile test was performed at a speed of 5 mm / min using an Instron 5581 type tensile tester. The maximum load until peeling was measured.
(5) Durability The thing apply | coated at 190 degreeC on the concrete flat plate was exposed outdoors for 12 months, and it visually observed whether there was any abnormality in the state of a coating material.
○: No abnormality △: Some bubbles are generated, but paint does not collapse ×: Paint collapses
[実施例1〜11]
表1に示す割合で原料を配合し、ニーダー混合機を用いて190℃で溶融混練し、各種評価を実施した。
[Examples 1 to 11]
The raw materials were blended at the ratios shown in Table 1, melt kneaded at 190 ° C. using a kneader mixer, and various evaluations were performed.
実施例1〜6では、L/D=5/95〜95/5、重量平均分子量5万であるポリ乳酸樹脂を粘結樹脂として使用し、着色剤、反射材、充填剤、可塑剤を本発明の範囲内で配合したものであるが、塗料の表面状態、施工性が良好で、密着強さにも優れることが分かる。耐久性に関しては、気泡が発生するものの、塗料の崩壊は認められない。実施例7、8は、粘結樹脂にL/D=99.5/0.5、重量平均分子量5万のポリ乳酸樹脂を使用したものであり、ポリ乳酸の結晶化により塗膜密着強さがやや低い傾向ではあるが、実用上問題ないレベルである。耐久性に関しても、塗料の崩壊は認められない。実施例9は、粘結樹脂にL/D=95/5、重量平均分子量15万であるポリ乳酸樹脂を使用したものであり、分子量が高く流動性が低いため、施工性がやや劣るものの、塗料として実用上問題ないレベルである。実施例10、11はカルボキシル基反応性末端封鎖剤を配合したものであり、耐久性が向上していることが分かる。 In Examples 1 to 6, a polylactic acid resin having L / D = 5/95 to 95/5 and a weight average molecular weight of 50,000 is used as a caking resin, and a coloring agent, a reflective material, a filler, and a plasticizer are used. Although blended within the scope of the invention, it can be seen that the surface state and workability of the paint are good and the adhesion strength is also excellent. Regarding the durability, although the bubbles are generated, the paint is not collapsed. In Examples 7 and 8, a polylactic acid resin having L / D = 99.5 / 0.5 and a weight average molecular weight of 50,000 was used as the binder resin, and the adhesion strength of the coating film was obtained by crystallization of polylactic acid. However, it is at a level where there is no problem in practical use. In terms of durability, no paint collapse is observed. In Example 9, a polylactic acid resin having L / D = 95/5 and a weight average molecular weight of 150,000 is used as the binder resin, and the workability is slightly inferior because the molecular weight is high and the fluidity is low. It is at a level where there is no practical problem as a paint. In Examples 10 and 11, a carboxyl group-reactive end-blocking agent is blended, and it can be seen that the durability is improved.
[比較例1〜3]
表2に示す割合で原料を配合し、ニーダー混合機を用いて190℃で溶融混練し、各種評価を実施した。
[Comparative Examples 1-3]
The raw materials were blended in the proportions shown in Table 2, and melt kneaded at 190 ° C. using a kneader mixer, and various evaluations were performed.
比較例1〜2は、粘結樹脂にポリ乳酸樹脂を使用し、着色剤、反射材の配合量を本発明の範囲を超えて配合したものであるが、塗料の表面状態、施工性、密着強さに劣ることが分かる。比較例3は、粘結樹脂に石油樹脂を使用したものであり、施工性や密着強さ、耐久性に優れるものの、環境負荷が高い。 In Comparative Examples 1 and 2, a polylactic acid resin is used for the binder resin, and the blending amount of the colorant and the reflector exceeds the range of the present invention. You can see that it is inferior in strength. Comparative Example 3 uses a petroleum resin as a caking resin and is excellent in workability, adhesion strength, and durability, but has a high environmental load.
本発明の熱溶融型塗料組成物は、ポリ乳酸樹脂を含有することを特徴とした塗料組成物であり、従来の石油系塗料組成物に比べ、環境負荷を低減することができる。
The hot-melt coating composition of the present invention is a coating composition characterized by containing a polylactic acid resin, and can reduce the environmental burden compared to conventional petroleum coating compositions.
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013009895A JP6111079B2 (en) | 2012-01-27 | 2013-01-23 | Hot melt coating composition |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012014943 | 2012-01-27 | ||
JP2012014943 | 2012-01-27 | ||
JP2013009895A JP6111079B2 (en) | 2012-01-27 | 2013-01-23 | Hot melt coating composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2013173925A true JP2013173925A (en) | 2013-09-05 |
JP6111079B2 JP6111079B2 (en) | 2017-04-05 |
Family
ID=49267106
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013009895A Active JP6111079B2 (en) | 2012-01-27 | 2013-01-23 | Hot melt coating composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP6111079B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015205994A (en) * | 2014-04-21 | 2015-11-19 | 東洋紡株式会社 | Polylactic acid base resin for thermofusion type road-marking coating material and thermofusion type road-marking coating composition |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001354841A (en) * | 2000-06-16 | 2001-12-25 | Showa Highpolymer Co Ltd | Aqueous dispersion of biodegradable polyester |
JP2004277475A (en) * | 2003-03-13 | 2004-10-07 | Sekisui Jushi Co Ltd | Road-marking paint and road-marking method |
JP2005015597A (en) * | 2003-06-25 | 2005-01-20 | Nippon Zeon Co Ltd | Petroleum resin composition and hot-melt type road-marking coating material composition |
JP2007326993A (en) * | 2006-06-09 | 2007-12-20 | Kictec Inc | Road-marking coating composition |
JP2011144318A (en) * | 2010-01-18 | 2011-07-28 | Teijin Ltd | Polylactic acid resin composition |
-
2013
- 2013-01-23 JP JP2013009895A patent/JP6111079B2/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001354841A (en) * | 2000-06-16 | 2001-12-25 | Showa Highpolymer Co Ltd | Aqueous dispersion of biodegradable polyester |
JP2004277475A (en) * | 2003-03-13 | 2004-10-07 | Sekisui Jushi Co Ltd | Road-marking paint and road-marking method |
JP2005015597A (en) * | 2003-06-25 | 2005-01-20 | Nippon Zeon Co Ltd | Petroleum resin composition and hot-melt type road-marking coating material composition |
JP2007326993A (en) * | 2006-06-09 | 2007-12-20 | Kictec Inc | Road-marking coating composition |
JP2011144318A (en) * | 2010-01-18 | 2011-07-28 | Teijin Ltd | Polylactic acid resin composition |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015205994A (en) * | 2014-04-21 | 2015-11-19 | 東洋紡株式会社 | Polylactic acid base resin for thermofusion type road-marking coating material and thermofusion type road-marking coating composition |
Also Published As
Publication number | Publication date |
---|---|
JP6111079B2 (en) | 2017-04-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5460576B2 (en) | Branched polyester for powder coating | |
JP5825919B2 (en) | Resin base for light reflector | |
TW200422360A (en) | Powder coating compositions containing anhydride end-capped crystalline polyesters | |
JP2007119730A (en) | Resin composition and molded article composed of the same | |
JP2012532936A (en) | Low temperature curing powder coating composition | |
TW200403311A (en) | Semi-gloss powder coating compositions | |
JP2009013364A (en) | Powder coating composition | |
WO2020100727A1 (en) | Flame-retardant polybutylene terephthalate resin composition | |
JP6111079B2 (en) | Hot melt coating composition | |
JP2007092038A (en) | Resin composition and molded product formed out thereof | |
WO2022037660A1 (en) | Polyester resin composition and molded article thereof | |
CN102388087B (en) | Powder coating composition | |
JP2011074327A (en) | Injection-molded material for automobile interior part, and molding thereof | |
JP4996668B2 (en) | POLYLACTIC ACID RESIN COMPOSITION, PROCESS FOR PRODUCING POLYLACTIC ACID RESIN COMPOSITION, MOLDED ARTICLE, DESK HOLDER FOR MOBILE PHONE, MOBILE PHONE INTERNAL CHASSIS COMPONENT, ELECTRONIC DEVICE CASE, ELECTRONIC DEVICE INTRODUCTION COMPONENT | |
WO2018225466A1 (en) | Curing accelerator for oxidatively polymerized unsaturated resin, printing ink, and paint | |
JP2015205994A (en) | Polylactic acid base resin for thermofusion type road-marking coating material and thermofusion type road-marking coating composition | |
JP4151398B2 (en) | Condensation-type thermoplastic resin composition and use thereof | |
JP2010195914A (en) | Glass-based inorganic filler-reinforced polyester resin composition | |
JPS6028446A (en) | Thermoplastic polyester resin composition | |
Yang et al. | Preparation, crystallization behavior, and melting characteristics of β‐nucleated isotactic polypropylene blends with polyamide 6 | |
JP2014125502A (en) | Zirconia containing epoxy resin composition | |
JP2009215372A (en) | Matte powdered coating material composition and method for forming coating film | |
JP2010285576A (en) | Thermoplastic resin composition | |
TW201840704A (en) | Resin cleaning agent and method for melt molding polyester resin | |
JP2008222865A (en) | Biomass resin composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20151113 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20160711 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20160715 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160908 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20170228 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20170313 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6111079 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313117 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |