JPWO2018139329A1 - (メタ)アクリロイル基含有アクリル変性アルキド樹脂及び無機材料薄膜用アンダーコート剤 - Google Patents
(メタ)アクリロイル基含有アクリル変性アルキド樹脂及び無機材料薄膜用アンダーコート剤 Download PDFInfo
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- JPWO2018139329A1 JPWO2018139329A1 JP2018564521A JP2018564521A JPWO2018139329A1 JP WO2018139329 A1 JPWO2018139329 A1 JP WO2018139329A1 JP 2018564521 A JP2018564521 A JP 2018564521A JP 2018564521 A JP2018564521 A JP 2018564521A JP WO2018139329 A1 JPWO2018139329 A1 JP WO2018139329A1
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- Prior art keywords
- meth
- acrylate
- alkyd resin
- acryloyl group
- mass
- 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.)
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- 229920000180 alkyd Polymers 0.000 title claims abstract description 110
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 title claims abstract description 95
- 229910010272 inorganic material Inorganic materials 0.000 title claims abstract description 33
- 239000011147 inorganic material Substances 0.000 title claims abstract description 33
- 239000010409 thin film Substances 0.000 title claims abstract description 29
- 239000011342 resin composition Substances 0.000 claims abstract description 45
- 239000011248 coating agent Substances 0.000 claims abstract description 35
- 238000000576 coating method Methods 0.000 claims abstract description 35
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 22
- -1 acrylate compound Chemical class 0.000 claims description 91
- 239000004925 Acrylic resin Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 43
- 229920000178 Acrylic resin Polymers 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 239000002994 raw material Substances 0.000 claims description 18
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 17
- 239000010408 film Substances 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 12
- 229920001228 polyisocyanate Polymers 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 abstract description 53
- 239000011347 resin Substances 0.000 abstract description 53
- 239000000758 substrate Substances 0.000 abstract description 36
- 239000003960 organic solvent Substances 0.000 abstract description 19
- 239000000463 material Substances 0.000 abstract description 15
- 239000003125 aqueous solvent Substances 0.000 abstract description 10
- 238000010790 dilution Methods 0.000 abstract description 5
- 239000012895 dilution Substances 0.000 abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 122
- 239000000047 product Substances 0.000 description 35
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 27
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 27
- 239000000178 monomer Substances 0.000 description 27
- 239000007787 solid Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 23
- 239000003921 oil Substances 0.000 description 22
- 235000019198 oils Nutrition 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 150000004665 fatty acids Chemical class 0.000 description 21
- 239000010410 layer Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 20
- 235000014113 dietary fatty acids Nutrition 0.000 description 19
- 229930195729 fatty acid Natural products 0.000 description 19
- 239000000194 fatty acid Substances 0.000 description 19
- 125000005702 oxyalkylene group Chemical group 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 150000002596 lactones Chemical class 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000011247 coating layer Substances 0.000 description 14
- 125000006353 oxyethylene group Chemical group 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- 229920000193 polymethacrylate Polymers 0.000 description 13
- 239000003822 epoxy resin Substances 0.000 description 11
- 239000003925 fat Substances 0.000 description 11
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000002585 base Substances 0.000 description 10
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 9
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 8
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 239000004359 castor oil Substances 0.000 description 8
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000004412 Bulk moulding compound Substances 0.000 description 6
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 239000004734 Polyphenylene sulfide Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000002159 abnormal effect Effects 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000004386 diacrylate group Chemical group 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 229920000069 polyphenylene sulfide Polymers 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- 230000008961 swelling Effects 0.000 description 6
- 230000002087 whitening effect Effects 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000000944 linseed oil Substances 0.000 description 5
- 235000021388 linseed oil Nutrition 0.000 description 5
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- 229920001707 polybutylene terephthalate Polymers 0.000 description 5
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 239000003784 tall oil Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 4
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 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 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
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- LATKICLYWYUXCN-UHFFFAOYSA-N naphthalene-1,3,6-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 LATKICLYWYUXCN-UHFFFAOYSA-N 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- 239000012994 photoredox catalyst Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Natural products OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D187/00—Coating compositions based on unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
- C09D187/005—Block or graft polymers not provided for in groups C09D101/00 - C09D185/04
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/06—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4288—Polycondensates having carboxylic or carbonic ester groups in the main chain modified by higher fatty oils or their acids or by resin acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
- C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
- C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
- C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
- C08G81/027—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyester or polycarbonate sequences
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
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- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
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- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Laminated Bodies (AREA)
- Paints Or Removers (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
カラム ;東ソー株式会社製 TSKgel 4000HXL、TSKgel 3000HXL、TSKgel 2000HXL、TSKgel 1000HXL
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII 測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
カラム ;東ソー株式会社製 TSKgel 4000HXL、TSKgel 3000HXL、TSKgel 2000HXL、TSKgel 1000HXL
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII 測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
攪拌棒、温度センサー、コンデンサ、滴下ロートを有するフラスコに、脱水ヒマシ油脂肪酸420質量部、工業用キシレン486質量部を仕込んだ。乾燥窒素をフラスコ内に流入させながら攪拌し、130℃まで加熱した。次いで、イソブチルメタクリレート305質量部、メタクリル酸255質量部、スチレン203質量部、ターシャリーブチルパーオキシベンゾエート(日油株式会社製「パーブチルZ」)38質量部、及び工業用キシレン38質量部の混合溶液を滴下ロートから3時間かけて滴下した。130℃で更に2時間撹拌を続け、粘度が変化しなくなったことを確認した後、60℃まで冷却した。メチルエチルケトンを加えて樹脂固形分が60質量%になるよう希釈し、アクリル樹脂中間体(X−1)溶液を得た。アクリル樹脂中間体(A−1)の油長は35、酸価は205.1mgKOH/g、数平均分子量(Mn)は1,400、重量平均分子量(Mw)は7,000であった。
攪拌棒、温度センサー、コンデンサを有するフラスコに、イソホロンジイソシアネート65.5質量部、2,6−ジターシャリーブチル−4−メチルフェノール(精工化学株式会社製「BHTスワノックス」)0.1質量部、メトキノン0.01質量部、ウレタン化触媒(日東化成株式会社製「ネオスタンU−830」)0.01質量部を仕込んだ。乾燥窒素をフラスコ内に流入させながら攪拌し、60℃まで加熱した。次いで、2−ヒドロキシエチルアクリレート34.5質量部を仕込み、70〜90℃まで加熱して反応させた。イソシアネート基含有量が12.3質量%になったところで、前記アクリル変性アルキド樹脂(1)溶液(樹脂固形分70質量%)2320質量部を仕込み反応させた。NCOイソシアネート基含有量が0.05質量%以下になったところで冷却を開始し、メチルエチルケトンを加えて樹脂固形分が70質量%になるように希釈して、(メタ)アクリロイル基含有アクリル変性アルキド樹脂(1)溶液を得た。(メタ)アクリロイル基含有アクリル変性アルキド樹脂(1)の油長は43、酸価は60.6mgKOH/g、数平均分子量(Mn)は2,200、重量平均分子量(Mw)は126,000であった。
攪拌棒、温度センサー、コンデンサを有するフラスコに、イソホロンジイソシアネート31.6質量部、2,6−ジターシャリーブチル−4−メチルフェノール(精工化学株式会社製「BHTスワノックス」)0.1質量部、メトキノン0.01質量部、ウレタン化触媒(日東化成株式会社製「ネオスタンU−830」)0.01質量部を仕込み、乾燥窒素をフラスコ内に流入させながら攪拌し、60℃まで加熱した。次いで、東亞合成株式会社製「アロニックス M−305」(ペンタエリスリトールトリアクリレートとペンタエリスリトールテトラアクリレートの混合物、水酸基価117mgKOH/g)68.4質量部を仕込み、70〜90℃まで加熱して反応させた。イソシアネート基含有量が5.96質量%になったところで、前記アクリル変性アルキド樹脂(1)溶液(樹脂固形分70質量%)2125質量部を仕込み反応させた。イソシアネート基含有量が0.05質量%以下になったところで冷却を開始し、メチルエチルケトンを加えて樹脂固形分が70質量%になるように希釈して、(メタ)アクリロイル基含有アクリル変性アルキド樹脂(2)溶液を得た。(メタ)アクリロイル基含有アクリル変性アルキド樹脂(2)の油長は42、酸価は58.5mgKOH/g、数平均分子量(Mn)は2,400、重量平均分子量(Mw)は145,000であった。
攪拌棒、温度センサー、コンデンサを有するフラスコに、前記アクリル変性アルキド樹脂(1)溶液(樹脂固形分70質量%)666質量部、2−イソシアナトエチルアクリレート(昭和電工株式会社製「カレンズAOI」)33.7質量部、及びウレタン化触媒(日東化成株式会社製「ネオスタンU−830」)0.05質量部を仕込んだ。乾燥窒素をフラスコ内に流入させながら攪拌し、70〜90℃まで加熱して反応させた。イソシアネート基含有量が0.05質量%以下になったところで冷却を開始し、メチルエチルケトンを加えて樹脂固形分が70質量%になるように希釈して、(メタ)アクリロイル基含有アクリル変性アルキド樹脂(3)溶液を得た。(メタ)アクリロイル基含有アクリル変性アルキド樹脂(3)の油長は42、酸価は51.7mgKOH/g、数平均分子量(Mn)は2,000、重量平均分子量(Mw)は91,200であった。
攪拌棒、温度センサー、コンデンサを有するフラスコに、前記(メタ)アクリロイル基含有アクリル変性アルキド樹脂(1)溶液(樹脂固形分70質量%)643質量部、東亞合成株式会社製東亞合成株式会社製「アロニックス M−350」(エチレンオキシド変性トリメチロールプロパントリアクリレート)50質量部を仕込み、50℃まで加熱した。トリエチルアミン49.2質量部を仕込んだ後、室温まで冷却しながら3時間かけてイオン交換水974質量部を滴下した。減圧条件下で有機溶剤を留去し、イオン交換水を追加して樹脂固形分30質量%の活性エネルギー線硬化型樹脂組成物(1)を得た。
攪拌棒、温度センサー、コンデンサを有するフラスコに、前記(メタ)アクリロイル基含有アクリル変性アルキド樹脂(1)溶液(樹脂固形分70質量%)357質量部、東亞合成株式会社製「アロニックス M−305」(ペンタエリスリトールトリアクリレートとペンタエリスリトールテトラアクリレートの混合物、水酸基価117mgKOH/g)50質量部、及び新中村化学株式会社製「NKエステルA−400」(ポリエチレングリコールジアクリレート)200質量部を仕込み、乾燥窒素をフラスコ内に流入させながら攪拌し、50℃まで加熱した。トリエチルアミン28.1質量部を仕込んだ後、室温まで冷却しながら3時間かけてイオン交換水1059質量部を滴下した。減圧条件下で有機溶剤を留去し、イオン交換水を追加して樹脂固形分30質量%の活性エネルギー線硬化型樹脂組成物(2)を得た。
攪拌棒、温度センサー、コンデンサを有するフラスコに、前記(メタ)アクリロイル基含有アクリル変性アルキド樹脂(2)溶液(樹脂固形分70質量%)357質量部、東亞合成株式会社製「アロニックス M−305」(ペンタエリスリトールトリアクリレートとペンタエリスリトールテトラアクリレートの混合物、水酸基価117mgKOH/g)50質量部、及び新中村化学株式会社製「NKエステルA−400」(ポリエチレングリコールジアクリレート)200質量部を仕込み、50℃まで加熱した。トリエチルアミン26.4質量部を仕込んだ後、室温まで冷却しながら3時間かけてイオン交換水1060質量部を滴下した。減圧条件下で有機溶剤を留去し、イオン交換水を追加して樹脂固形分30質量%の活性エネルギー線硬化型樹脂組成物(3)を得た。
攪拌棒、温度センサー、コンデンサを有するフラスコに、前記(メタ)アクリロイル基含有アクリル変性アルキド樹脂(2)溶液(樹脂固形分70質量%)357質量部、東亞合成株式会社製「アロニックス M−305」(ペンタエリスリトールトリアクリレートとペンタエリスリトールテトラアクリレートの混合物、水酸基価117mgKOH/g)50質量部、新中村化学株式会社製「NKエステルA−400」(ポリエチレングリコールジアクリレート)100質量部、及び新中村化学株式会社製「NKエステルA−GLY−9E」(エチレンオキシド変性グリセリントリアクリレート)100質量部を仕込み、50℃まで加熱した。トリエチルアミン26.4質量部を仕込んだ後、室温まで冷却しながら3時間かけてイオン交換水1060質量部を滴下した。減圧条件下で有機溶剤を留去し、イオン交換水を追加して樹脂固形分30質量%の活性エネルギー線硬化型樹脂組成物(4)を得た。
攪拌棒、温度センサー、コンデンサを有するフラスコに、前記(メタ)アクリロイル基含有アクリル変性アルキド樹脂(2)溶液(樹脂固形分70質量%)357質量部、東亞合成株式会社製「アロニックス M−305」(ペンタエリスリトールトリアクリレートとペンタエリスリトールテトラアクリレートの混合物、水酸基価117mgKOH/g)50質量部、及び新中村化学株式会社製「NKエステルA−400」(ポリエチレングリコールジアクリレート)200質量部を仕込み、50℃まで加熱した。ジメチルアミノプロピルアクリルアミド40.7質量部を仕込んだ後、室温まで冷却しながら3時間かけてイオン交換水1060質量部を滴下した。減圧条件下で有機溶剤を留去し、イオン交換水を追加して樹脂固形分30質量%の活性エネルギー線硬化型樹脂組成物(5)を得た。
攪拌棒、温度センサー、コンデンサを有するフラスコに、前記(メタ)アクリロイル基含有アクリル変性アルキド樹脂(3)溶液(樹脂固形分70質量%)357質量部、東亞合成株式会社製「アロニックス M−305」(ペンタエリスリトールトリアクリレートとペンタエリスリトールテトラアクリレートの混合物、水酸基価117mgKOH/g)50質量部、及び新中村化学株式会社製「NKエステルA−400」(ポリエチレングリコールジアクリレート)200質量部を仕込み、50℃まで加熱した。トリエチルアミン23.3質量部を仕込んだ後、室温まで冷却しながら3時間かけてイオン交換水1060質量部を滴下した。減圧条件下で有機溶剤を留去し、イオン交換水を追加して樹脂固形分30質量%の活性エネルギー線硬化型樹脂組成物(6)を得た。
攪拌棒、温度センサー、コンデンサ、滴下ロートを有する加圧式フラスコに、メチルエチルケトン1076質量部を仕込み、加圧条件下で90℃まで加熱した。メチルメタクリレート850質量部、2−ヒドロキシエチルアクリレート200質量部、メトキシポリエチレングリコールアクリレート(新中村化学株式会社製「NKエステルAM−130G」)912質量部、メタクリル酸150質量部、及びターシャリーブチル(2−エチルヘキサノイル)パーオキシド(日油株式会社製「パーブチルO」)8.0質量部の混合溶液を滴下ロートから4時間かけて滴下した。滴下終了後、ジターシャリーブチルパーオキシド(日油株式会社製「パーブチルD」)1.0質量部を仕込み、加圧条件下120℃で3時間反応させ、重量平均分子量(Mw)12,400、酸価13mgKOH/g、水酸基価48mgKOH/gの中間体を得た。
表1〜3に示す割合で各成分を配合し、適宜イオン交換水を加えて樹脂固形分を30質量%に調整して活性エネルギー線硬化型樹脂組成物を製造した。
(メタ)アクリロイル基含有化合物(R−2):東亞合成株式会社「アロニックスM−403」(ジペンタエリスリトールペンタアクリレートとジペンタエリスリトールヘキサアクリレートとの混合物、水酸基価75mgKOH/g)
(メタ)アクリロイル基含有化合物(R−3):東亞合成株式会社「アロニックスM−305」(ペンタエリスリトールトリアクリレートとペンタエリスリトールテトラアクリレートの混合物、水酸基価117mgKOH/g)
(メタ)アクリロイル基含有化合物(R−4):MIWON社製「Miramer M220」(トリプロピレングリコールジアクリレート)
(メタ)アクリロイル基含有化合物(R−5):新中村化学株式会社製「NKエステルA−400」(ポリエチレングリコールジアクリレート)
(メタ)アクリロイル基含有化合物(R−6):新中村化学株式会社製「NKエステルA−GLY−9E」(エチレンオキシド変性グリセリントリアクリレート)
ポリカルボジイミド樹脂(1):日清紡ケミカル株式会社製「カルボジライトV−02−L2」
ポリカルボジイミド樹脂(2):日清紡ケミカル株式会社製「Elastostab H01」
オキサゾリン基含有樹脂(1):株式会社日本触媒製「エポクロスWS−500」
オキサゾリン基含有樹脂(2):株式会社日本触媒製「エポクロスWS−700」
光重合開始剤:BASFジャパン株式会社製「IRGACURE 500」
フッ素系添加剤:DIC株式会社製「MEGAFACE F−477」
シリコーン系添加剤:ビックケミー・ジャパン株式会社製「BYK−345」
先で得た活性エネルギー線硬化型樹脂組成物をプラスチック基材上にエアースプレー塗装した。80℃で10分間乾燥させた後、80W/cmの高圧水銀灯で1500mJ/cm2の紫外線を照射して、アンダーコート層を形成した。アンダーコート層の膜厚は15〜25μmの範囲であった。次に、真空蒸着装置を用い、アンダーコート層の表面に厚さ100nmのアルミニウム蒸着層を形成し、反射板を作成した。プラスチック基材は以下の三種類を用い、それぞれ反射板1〜3とした。
反射板1:基材としてPPS(ポリフェニレンスルフィド)板を用いた
反射板2:基材としてBMC(バルクモールディングコンパウンド)板を用いた
反射板3:基材としてABS(アクリロニトリル−ブタジエン−スチレン共重合樹脂)板を用いた。
先で得た活性エネルギー線硬化型樹脂組成物をポリカーボネート基材上にエアースプレー塗装した。80℃で10分間乾燥させた後、80W/cmの高圧水銀灯で1500mJ/cm2の紫外線を照射して、塗膜層を形成した。塗膜層の膜厚は15〜25μmの範囲であった。
反射板3の外観を下記基準で評価した。結果を表1〜3に示す。
「A」:平滑であり、「白化」、「虹」、「クラック」、「フクレ」等の外観異常が観察されない。
「B」:反射板の一部のみに「白化」、「虹」、「クラック」、「フクレ」等の外観異常が観察される。
「C」:反射板の全部に「白化」、「虹」、「クラック」、「フクレ」等の外観異常が観察される。
反射板1〜3の基剤密着性を以下の方法で評価した。結果を表1〜3に示す。
反射板1〜3の蒸着層側に2mm間隔で10×10の碁盤目状にカッターナイフで切れ目を入れ、4mm2の碁盤目を100個作成した。次いで、碁盤目上にセロハンテープを貼りつけた後、急速に剥がす試験を行い、ASTM D3359の例に準じて基材密着性を評価した。
また、反射板1については230℃の熱風乾燥機に24時間放置した後の基材密着性を同様にして評価した。反射板3については80℃の熱風乾燥機に24時間放置した後の基材密着性を同様にして評価した。
「5B」:試験後の剥離面積が0%。
「4B」:試験後の剥離面積が5%未満。
「3B」:試験後の剥離面積が5〜15%未満。
「2B」:試験後の剥離面積が15〜35%未満。
「1B」:試験後の剥離面積が35〜65%未満。
「0B」:試験後の剥離面積が65%以上。
実施例10〜15について、反射板3を80℃の熱風乾燥機に24時間放置した後の外観も同様に下記基準で評価した。いずれもA評価であった。
「A」:平滑であり、「白化」、「虹」、「クラック」、「フクレ」等の外観異常が観察されない。
「B」:反射板の一部のみに「白化」、「虹」、「クラック」、「フクレ」等の外観異常が観察される。
「C」:反射板の全部に「白化」、「虹」、「クラック」、「フクレ」等の外観異常が観察される。
実施例10〜24について、反射板1と3の熱処理後の基剤密着性を以下の方法で評価した。結果を表4に示す。
230℃の熱風乾燥機に24時間放置した反射板1と、80℃の熱風乾燥機に24時間放置した反射板3を用意した。
各反射板の蒸着層側に2mm間隔で10×10の碁盤目状にカッターナイフで切れ目を入れ、4mm2の碁盤目を100個作成した。次いで、碁盤目上にセロハンテープを貼りつけた後、急速に剥がす試験を行い、ASTM D3359の例に準じて基材密着性を評価した。
「5B」:試験後の剥離面積が0%。
「4B」:試験後の剥離面積が5%未満。
「3B」:試験後の剥離面積が5〜15%未満。
「2B」:試験後の剥離面積が15〜35%未満。
「1B」:試験後の剥離面積が35〜65%未満。
「0B」:試験後の剥離面積が65%以上。
実施例10〜15及び17〜25について、塗装板の塗膜層の上に、1N−硫酸水溶液を満たしたプラスチック製容器を設置して、25℃の環境下で24時間放置することにより、塗膜層の耐酸性試験を実施した。試験後の塗膜層の状態を目視で確認して、下記評価基準で評価した。いずれの塗装版もA評価であった。
「A」:試験した塗膜層に変化がない。
「B」:試験した塗膜層の一部に、白濁やブリスタが発生している。
「C」:試験した塗膜層の全体に、白濁やブリスタが発生している。
実施例10〜15について、先で得た塗装板の塗膜層の上に、0.1N−水酸化ナトリウム水溶液を満たしたプラスチック製容器を設置して、25℃の環境下で24時間放置することにより、塗膜層の耐アルカリ性試験を実施した。試験後の塗膜層の状態を目視で確認して、下記評価基準で評価した。結果を表5に示す。
「A」:試験した塗膜層に変化がない。
「B」:試験した塗膜層の一部に、白濁やブリスタが発生している。
「C」:試験した塗膜層の全体に、白濁やブリスタが発生している。
実施例10〜12、14、15及び17〜25について、塗装板の塗膜層側に、メチルエチルケトンを浸漬したフェルトを荷重500gで押し付けながら、10cmの距離を10回往復させるラビング試験を実施した。試験前後の塗装板のヘイズ値を測定し、下記評価基準で評価した。結果を表6に示す。
「A」:試試験前後のヘイズ値の差が1未満である。
「B」:試試験前後のヘイズ値の差が1以上3未満である。
「C」:試試験前後のヘイズ値の差が3以上である。
攪拌棒、温度センサー、コンデンサ、滴下ロートを有するフラスコに、脱水ヒマシ油脂肪酸420質量部、工業用キシレン486質量部を仕込んだ。乾燥窒素をフラスコ内に流入させながら攪拌し、130℃まで加熱した。次いで、イソブチルメタクリレート305質量部、メタクリル酸255質量部、スチレン203質量部、ターシャリーブチルパーオキシベンゾエート(日油株式会社製「パーブチルZ」)38質量部、及び工業用キシレン38質量部の混合溶液を滴下ロートから3時間かけて滴下した。130℃で更に2時間撹拌を続け、粘度が変化しなくなったことを確認した後、60℃まで冷却した。メチルエチルケトンを加えて樹脂固形分が60質量%になるよう希釈し、アクリル樹脂中間体(A−1)溶液を得た。アクリル樹脂中間体(A−1)の油長は35、酸価は205.1mgKOH/g、数平均分子量(Mn)は1,400、重量平均分子量(Mw)は7,000であった。
Claims (11)
- (メタ)アクリロイル基含有アクリル変性アルキド樹脂。
- アクリル樹脂中間体(A)、アルキド樹脂中間体(B)、ポリイソシアネート化合物(C)、及び水酸基含有(メタ)アクリレート化合物(D)を必須の反応原料とする反応生成物である請求項1記載の(メタ)アクリロイル基含有アクリル変性アルキド樹脂。
- アクリル樹脂中間体(A)、アルキド樹脂中間体(B)、及びイソシアネート基含有(メタ)アクリレート化合物(E)を必須の反応原料とする反応生成物である請求項1記載の(メタ)アクリロイル基含有アクリル変性アルキド樹脂。
- 前記アクリル樹脂中間体(A)の酸価が50〜300mgKOH/gの範囲であり、重量平均分子量(Mw)が1,000〜50,000の範囲である請求項2又は3に記載の(メタ)アクリロイル基含有アクリル変性アルキド樹脂。
- 前記アクリル樹脂中間体(A)の油長が10以上である請求項4記載の(メタ)アクリロイル基含有アクリル変性アルキド樹脂。
- 前記アルキド樹脂中間体(B)の油長が10以上であり、重量平均分子量(Mw)が1,000〜100,0000の範囲である請求項2又は3に記載の(メタ)アクリロイル基含有アクリル変性アルキド樹脂。
- 前記ポリイソシアネート化合物(C)が、分子構造中に環構造を有するポリイソシアネート化合物である請求項2記載の(メタ)アクリロイル基含有アクリル変性アルキド樹脂。
- 請求項1〜6のいずれか一つに記載の(メタ)アクリロイル基含有アクリル変性アルキド樹脂を含有する活性エネルギー線硬化型樹脂組成物。
- 請求項7記載の活性エネルギー線硬化型樹脂組成物を用いてなる無機材料薄膜用アンダーコート剤。
- 請求項8記載の無機材料薄膜用アンダーコート剤からなる塗膜。
- 請求項9記載の無機材料薄膜用アンダーコート剤からなるアンダーコート層を有する成形体。
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