CN101220193B - Soldifiable resin composition - Google Patents
Soldifiable resin composition Download PDFInfo
- Publication number
- CN101220193B CN101220193B CN2008100034267A CN200810003426A CN101220193B CN 101220193 B CN101220193 B CN 101220193B CN 2008100034267 A CN2008100034267 A CN 2008100034267A CN 200810003426 A CN200810003426 A CN 200810003426A CN 101220193 B CN101220193 B CN 101220193B
- Authority
- CN
- China
- Prior art keywords
- methyl
- curable resin
- mentioned
- compound
- resin composition
- 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.)
- Expired - Fee Related
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- 239000011342 resin composition Substances 0.000 title claims description 33
- -1 alkyl methacrylate ester Chemical class 0.000 claims abstract description 104
- 239000011347 resin Substances 0.000 claims abstract description 71
- 229920005989 resin Polymers 0.000 claims abstract description 71
- 239000000178 monomer Substances 0.000 claims abstract description 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 38
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 23
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 239000005056 polyisocyanate Substances 0.000 claims description 31
- 229920001228 polyisocyanate Polymers 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 claims description 24
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 19
- 239000004593 Epoxy Substances 0.000 claims description 16
- 150000002148 esters Chemical group 0.000 claims description 15
- 229920000178 Acrylic resin Polymers 0.000 claims description 14
- 239000004925 Acrylic resin Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 claims description 5
- UTSYWKJYFPPRAP-UHFFFAOYSA-N n-(butoxymethyl)prop-2-enamide Chemical compound CCCCOCNC(=O)C=C UTSYWKJYFPPRAP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- XZXYVKWNNYKLGA-UHFFFAOYSA-N n-(2-methylpropoxy)prop-2-enamide Chemical compound CC(C)CONC(=O)C=C XZXYVKWNNYKLGA-UHFFFAOYSA-N 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 238000000576 coating method Methods 0.000 abstract description 14
- 239000011248 coating agent Substances 0.000 abstract description 13
- 229920001577 copolymer Polymers 0.000 abstract description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 80
- 238000013461 design Methods 0.000 description 26
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 21
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 239000012467 final product Substances 0.000 description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 9
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 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 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000013638 trimer Substances 0.000 description 7
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 6
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 6
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 6
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 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 5
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000005864 Sulphur Substances 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 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 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 4
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 4
- QFEDAUICQTVZJL-UHFFFAOYSA-N 3-ethyl-4-prop-2-enoyloxyphthalic acid Chemical compound CCC1=C(OC(=O)C=C)C=CC(C(O)=O)=C1C(O)=O QFEDAUICQTVZJL-UHFFFAOYSA-N 0.000 description 4
- 241000723346 Cinnamomum camphora Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 4
- 229960000846 camphor Drugs 0.000 description 4
- 229930008380 camphor Natural products 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000001883 metal evaporation Methods 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 3
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- 239000004632 polycaprolactone Substances 0.000 description 3
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
- OSQBFLZKVLCVGI-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-carbonyl 1,2,3,4-tetrahydronaphthalene-1-carboxylate Chemical compound C1CCC2=CC=CC=C2C1C(=O)OC(=O)C1C2=CC=CC=C2CCC1 OSQBFLZKVLCVGI-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 229940043232 butyl acetate Drugs 0.000 description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
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- QENDLNJWYIFMIM-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-n-methylprop-2-enamide Chemical compound CN(C)CCCN(C)C(=O)C=C QENDLNJWYIFMIM-UHFFFAOYSA-N 0.000 description 1
- MUEWNDFFTQLUAF-UHFFFAOYSA-N n-methyl-n-(2-methylpropoxy)prop-2-enamide Chemical compound CC(C)CON(C)C(=O)C=C MUEWNDFFTQLUAF-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YUIVHZARNDKOHO-UHFFFAOYSA-N n-tert-butyl-n-methylprop-2-enamide Chemical compound CC(C)(C)N(C)C(=O)C=C YUIVHZARNDKOHO-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000007601 warm air drying Methods 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention provides a cured resin combination capable of forming a coating film with an excellent bindability and appearance for a hard bonding resin. The invention solves the difficulty by providing the cured resin combination, wherein the cured resin combination comprises a copolymer and a cured resin. The copolymer is obtained by polymerizing (methyl) alkyl methacrylate ester, methacrylamide monomer and vinyl monomer with carboxyls.
Description
Technical field
The present invention relates to curable resin composition.
Background technology
The plastics that acrylic resin, polycarbonate resin, polystyrene resin, ABS resin are such since be light weight, have excellent in impact resistance, forming process and low price, so in various fields, be used.
And the moulding product of plastics are purpose to protect its surface not sustain damage etc., generally with the lining of filming.
For example; in patent documentation 1; its purpose is to be provided for to form the Photocurable resin composition that the polyolefin surface modification of the cured coating film of wear-resisting wiping and adhesivity excellence is used at polyolefin surfaces; recorded and narrated a kind of polyolefin surface modification Photocurable resin composition; it is characterized in that; contain (A) composition; (B) composition; (C) composition and (D) composition; wherein (A) composition is to be selected from imperplex; methyl methacrylate content is the above methyl methacrylate based copolymers of 80 weight %; with at methyl methacrylate content be at least a kind the polymkeric substance of introducing in the side chain of the methyl methacrylate based copolymer more than the 80 weight % in the modifier that (methyl) acryl forms; (B) composition is the polyfunctional acrylic ester that contains the above dipentaerythritol acrylate of 50 weight %; (C) composition is a solvent; (D) composition is a Photoepolymerizationinitiater initiater, and (A) weight ratio of the composition of composition/(B) in 0.1～10 scope.
In addition, in patent documentation 2, it is that the surface of the moulding product of resin formation is provided with adhesivity that its purpose is to be provided at by thermoplastic norbornene, wearability, chemical resistant properties, thermotolerance, the moulding product of the hard coat that outward appearance etc. are excellent, with its manufacture method, recorded and narrated a kind of have make following ultra-violet solidified composition solidify the thermoplastic norbornene based resin molded articles of the hard coat that forms, described ultra-violet solidified composition comprises (A) monomer mixture of 10～90 weight parts, (B) coating resin of 5～80 weight parts, (C) Photoepolymerizationinitiater initiater with 0.1～15 weight part, described monomer mixture is by the multi-functional monomer (a-1) that has (methyl) acryloxy more than 3 in 1 molecule of 20～100 weight %, form with 1～2 functional monomer (a-2) who has (methyl) acryloxy of 1～2 in 1 molecule of 80～0 weight %, described coating resin is formed by a kind monomeric homopolymer of monomeric ethene base system or the multipolymer being selected from (methyl) esters of acrylic acid that contain more than the 10 weight % at least.
In patent documentation 3, also be difficult to the optical polymerism compound of hydrolysis, be preferably used as corroding metal plate as high-quality shadow mask (shadowmask) or lead frame and the ultraviolet-curing resin composition of the cured film used when forming etched figure even its purpose is to provide to contain at ester bond in the acid high temperature etching solution, recorded and narrated a kind of ultraviolet-curing resin composition, it is characterized in that, contain useful Chemical formula 1 [CH at least
2=CR ' COO (CH
2CHR " COO)
nH] optical polymerism compound, polyfunctional monomer and the polymerization starter (in Chemical formula 1, n is 0～3, R ', R " be H or methyl) of expression.
In patent documentation 4; with the ultra-violet solidified composition that provides the metal etch protection against corrosion to use is purpose; the ultra-violet solidified composition that described metal etch protection against corrosion is used is compared with the anticorrosive agent of existing water soluble resin type or ultraviolet hardening; has excellent erosion resistance for acid etching liquid; has the formation of filming uniformly of not having the coating spot; and a part of stripping that does not make the constituent material of filming is in etching solution; has high microfabrication precision; utilize alkali lye easily to peel off; recorded and narrated the ultra-violet solidified composition that the metal etch protection against corrosion of a kind of acid resistance and alkali-soluble is used; it is characterized in that; contain (methyl) acrylic compound (A composition) that has at least 1 carboxyl and at least 1 (methyl) acryl endways; multifunctional (methyl) acrylate and/or simple function (methyl) acrylate (B composition) beyond the A composition; and Photoepolymerizationinitiater initiater (C composition), described Photoepolymerizationinitiater initiater (C composition) contains the compound with ad hoc structure.
[patent documentation 1] special fair 7-91489 communique
No. 3377301 communique of [patent documentation 2] patent
[patent documentation 3] spy opens the 2001-354730 communique
[patent documentation 4] spy opens the 2002-20411 communique
Summary of the invention
But the composition of recording and narrating in patent documentation 1～2 and the binding property of difficult resin of binding property are insufficient.In addition, the composition of recording and narrating in the patent documentation 3～4, under the situation of coating difficult resin of binding property face, have obtain film on produce problem concavo-convex, appearance design decline.
Therefore, the object of the present invention is to provide a kind of curable resin composition, it can form has filming of excellent adhesiveness and appearance design to difficult resin of binding property.
The present inventor has carried out making great efforts research, found that the curable resin composition that contains multipolymer (A) and curable resin (B) can form difficult resin of binding property is had filming of excellent adhesiveness and appearance design, described multipolymer (A) is the multipolymer that the monomer component that contains (methyl) alkyl acrylate (a1), (methyl) acrylamide monomer (a2) and have the vinyl monomer (a3) of carboxyl is polymerized, thereby has finished the present invention.
That is, the invention provides following (1)～(10).
(1) a kind of curable resin composition, it contains multipolymer (A) and curable resin (B), and described multipolymer (A) is the multipolymer that the monomer component that contains (methyl) alkyl acrylate (a1), (methyl) acrylamide monomer (a2) and have the vinyl monomer (a3) of carboxyl is polymerized.
(2) as above-mentioned (1) described curable resin composition, above-mentioned (methyl) acrylamide monomer (a2) is the compound with following formula (1) expression,
CH
2＝CR
1-CO-NH-R
2 (1)
(in the formula, R
1Be hydrogen atom or methyl, R
2Be to contain at least a kind of heteroatomic alkyl that is selected from Sauerstoffatom, nitrogen-atoms and the sulphur atom).
(3) as above-mentioned (2) described curable resin composition, the compound of representing with following formula (1) is at least a kind the compound that is selected from N-methoxyl group propylene acid amides, N-isobutoxy acrylamide, dimethylaminopropyl Methacrylamide and the N-butoxymethyl acrylamide.
(4) as each described curable resin composition of above-mentioned (1)～(3), the weight-average molecular weight of above-mentioned multipolymer (A) is 10,000～150,000.
(5) as each described curable resin compositions of above-mentioned (1)～(4), in above-mentioned monomer component 100 mass parts of above-mentioned multipolymer (A), contain above-mentioned (methyl) alkyl acrylate (a1) of 20～90 mass parts, above-mentioned (methyl) the acrylamide monomer (a2) of 1～50 mass parts and the above-mentioned vinyl monomer (a3) of 1～50 mass parts.
(6) as each described curable resin compositions of above-mentioned (1)～(5), the content of above-mentioned curable resin (B) is 1～1,000 mass parts with respect to the above-mentioned multipolymer (A) of 100 mass parts.
(7) as each described curable resin composition of above-mentioned (1)～(6), above-mentioned curable resin (B) is polyisocyanate compound (B1),
And then contain aromatics (C), and it is the aromatics with hydroxyl, above-mentioned hydroxyl is combined on the aromatic nucleus by the aliphatics or the ester ring type alkyl of divalent.
(8) as above-mentioned (7) described curable resin composition, above-mentioned aromatics (C) is the compound with following formula (2) expression,
(in the formula, n represents 1～3 integer).
(9) as each described curable resin composition of above-mentioned (1)～(6), above-mentioned curable resin (B) is light solidified acrylic resin (B2),
And then contain Photoepolymerizationinitiater initiater (D).
(10) as each described curable resin composition of above-mentioned (1)～(6), above-mentioned curable resin (B) is Resins, epoxy (B3),
And then contain the solidifying agent (E) of above-mentioned Resins, epoxy (B3).
Curable resin composition of the present invention can form has filming of excellent adhesiveness and appearance design to difficult resin of binding property.
Embodiment
Below, and then explain the present invention.
Curable resin composition of the present invention (below, be also referred to as " composition of the present invention ") be the composition that contains multipolymer (A) and curable resin (B), described multipolymer (A) is to make the monomer component that contains (methyl) alkyl acrylate (a1), (methyl) acrylamide monomer (a2) and have the vinyl monomer (a3) of carboxyl carry out polymerization and the multipolymer that obtains.
＜multipolymer (A) 〉
The multipolymer that uses in composition of the present invention (A) is to make the monomer component that contains (methyl) alkyl acrylate (a1), (methyl) acrylamide monomer (a2) and have the vinyl monomer (a3) of carboxyl carry out polymerization and the multipolymer that obtains.
Below describe for (methyl) alkyl acrylate (a1).
As (methyl) alkyl acrylate (a1) of multipolymer (A1) monomer component, can enumerate the compound of for example using following formula (3) expression.
In the formula, R
3Be hydrogen atom or methyl.R
4Be that carbonatoms is that 1～30 alkyl, preferred carbonatoms are 1～20 alkyl, more preferably carbonatoms is 1～15 alkyl.
As (methyl) alkyl acrylate (a1), for example can enumerate (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, (methyl) butyl acrylate etc.
Wherein preferable methyl methyl acrylate, butyl methacrylate.
(methyl) alkyl acrylate (a1) can be distinguished separately or use making up more than 2 kinds.
The usage quantity of (methyl) alkyl acrylate (a1) is preferably 20～90 mass parts, more preferably 25～85 mass parts and then preferred 30～80 mass parts in the monomer component of the multipolymer (A) of 100 mass parts.
Below (methyl) acrylamide monomer (a2) is described.
As (methyl) acrylamide monomer (a2) of multipolymer (A1) monomer component, so long as have CH
2=CR
1-CO-NH-(in the formula, R
1Be hydrogen atom or methyl) compound get final product, limit especially.
As (methyl) acrylamide monomer (a2), can enumerate the compound of for example using following formula (1) expression.
CH
2＝CR
1-CO-NH-R
2 (1)
(in the formula, R
1Be hydrogen atom or methyl, R
2Be to contain at least a kind of heteroatomic alkyl that is selected from Sauerstoffatom, nitrogen-atoms and the sulphur atom)
Alkyl is not limited especially, can enumerate for example methyl, ethyl, propyl group, amyl group, the such saturated hydrocarbyl of hexyl; The ester ring type alkyl that cyclohexyl is such; Phenyl, the such aromatic hydrocarbyl of tolyl; Methoxyl group, oxyethyl group, butoxy, the such alkoxyl group of isobutoxy; Phenoxy group; The alkyl that butoxymethyl is such with ehter bond; The alkyl that contains nitrogen-atoms that dimethylaminopropyl is such; Methylthio group, ethylmercapto group, rosickyite base, the such alkyl that contains sulphur atom of phenyl sulfenyl.
From to the more excellent viewpoint of binding property, the appearance design of difficult resin of binding property, (methyl) acrylamide monomer (a2) is preferably used the compound of formula (1) expression.
As compound, can enumerate for example N-methoxyl group (methyl) acrylamide, N-isobutoxy (methyl) acrylamide, dimethylaminopropyl (methyl) acrylamide, N-butoxymethyl (methyl) acrylamide, N-methylol (methyl) acrylamide, the N-tertiary butyl (methyl) acrylamide, N-ethoxyethyl group (methyl) acrylamide with formula (1) expression.
Wherein, from binding property, the more excellent viewpoint of appearance design, be preferably selected from least a kind compound in N-methoxyl group propylene acid amides, N-isobutoxy acrylamide, dimethylaminopropyl Methacrylamide and the N-butoxymethyl acrylamide with the compound of formula (1) expression to difficult resin of binding property.
(methyl) acrylamide monomer (a2) can be distinguished separately or use making up more than 2 kinds.
The usage quantity of (methyl) acrylamide monomer (a2) is preferably 1～50 mass parts, more preferably 5～45 mass parts and then preferred 10～40 mass parts in the monomer component of the multipolymer (A) of 100 mass parts.
Below vinyl monomer (a3) is described.
Vinyl monomer (a3) as multipolymer (A1) monomer component gets final product so long as have the compound of carboxyl and vinyl, does not limit especially.
Can enumerate for example compound of (methyl) vinylformic acid, usefulness following formula (4) expression.
CH
2＝CR
1-CO-O-R
5-COOH (4)
(in the formula, R
1Be hydrogen atom or methyl, R
5Be to contain the alkyl that is selected from least a kind of heteroatomic divalent in Sauerstoffatom, nitrogen-atoms and the sulphur atom)
As the alkyl of divalent, can enumerate for example methylene radical, ethylidene, trimethylene, tetramethylene, pentamethylene, the such aliphatic alkyl of hexa-methylene; The aromatic hydrocarbyl that phenylene is such;-CH
2CH-OOC-C
6H
4Alkyl like this with ester bond.
From viewpoint to the binding property excellence of base material, preferred (methyl) vinylformic acid of vinyl monomer (a3), with the compound of formula (4) expression.
As compound, can enumerate for example acryloxy ethyl phthalic acid, ω-carboxyl polycaprolactone list (methyl) acrylate, (methyl) acrylic acid dimer with formula (4) expression.
From the viewpoint that the binding property of base material, excellent in te pins of durability, the hardness of filming are increased, vinyl monomer (a3) is preferably selected from least a kind compound in vinylformic acid, methacrylic acid and the acryloxy ethyl phthalic acid.
Vinyl monomer (a3) can be distinguished separately or use making up more than 2 kinds.
The usage quantity of vinyl monomer (a3) is preferably 1～50 mass parts, more preferably 5～45 mass parts and then preferred 10～40 mass parts in the monomer component of the multipolymer (A) of 100 mass parts.
Monomer component as multipolymer (A), under the scope of not damaging the object of the invention, except (methyl) alkyl acrylate (a1), (methyl) acrylamide monomer (a2) and vinyl monomer (a3), can also use other copolymerizable unsaturated monomer.
As other copolymerizable unsaturated monomer, can enumerate for example ethylenically unsaturated monomer of vinylbenzene, vinyl-acetic ester, (methyl) vinyl cyanide etc.
From accessing the angle of filming with special excellent adhesiveness and appearance design, the preferred following terpolymer of multipolymer (A), described terpolymer make methyl methacrylate or butyl methacrylate, be selected from least a kind of compound in N-methoxyl group propylene acid amides, N-isobutoxy acrylamide, dimethylaminopropyl Methacrylamide and the N-butoxymethyl acrylamide, be selected from least a kind of compound in vinylformic acid, methacrylic acid and the acryloxy ethyl phthalic acid and carry out polymerization and obtain.
The manufacture method of multipolymer (A) is limited especially, for example can by in the presence of polymerization starter, make (methyl) alkyl acrylate (a1), (methyl) acrylamide monomer (a2) and vinyl monomer (a3) carry out in solvent that radical polymerization is incompatible to be obtained.
Binding property, the excellent more viewpoint of appearance design from composition, amount that use when making multipolymer (A), (methyl) alkyl acrylate (a1), (methyl) acrylamide monomer (a2) and vinyl monomer (a3) is preferably, be used for making the monomer component of multipolymer (A) in 100 mass parts, (methyl) alkyl acrylate (a1) is that 20～90 mass parts, (methyl) acrylamide monomer (a2) are that 1～50 mass parts, vinyl monomer (a3) are 1～50 mass parts.
As solvent, can enumerate the ketone etc. of the aliphatics alcohols, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), pimelinketone etc. of the ester class, n-propyl alcohol, isopropyl alcohol etc. of aromatic hydrocarbon based, the ethyl acetate, butylacetate etc. of for example toluene, dimethylbenzene etc.
As polymerization starter, can enumerate for example Diisopropyl azodicarboxylate, benzoyl peroxide, ditertiary butyl peroxide, cumene hydroperoxide etc.
The viewpoint that, binding property suitable from viscosity, appearance design are excellent more, the weight-average molecular weight of multipolymer (A) is preferably 10,000～150, and 000, more preferably 20,000～100,000 and then preferred 30,000～80,000.
And the weight-average molecular weight in this specification sheets uses the polystyrene standard calibration value that obtains according to gel permeation chromatography (GCP) to represent.
Multipolymer (A) can use separately respectively or will be used in combination more than 2 kinds.
Multipolymer (A) not only can make composition lowering viscousity of the present invention, and and then can reduce contact angle to difficult resin of binding property, therefore film level and smooth and the appearance design excellence that is obtained by composition of the present invention.In addition because multipolymer (A) can be given binding property, so can access filming to the binding property excellence of difficult resin of binding property.
＜curable resin (B) 〉
As the curable resin that in composition of the present invention, uses (B), do not limit especially.Preferably enumerate polyisocyanate compound (B1), light solidified acrylic resin (B2), Resins, epoxy (B3).Curable resin (B) can be given binding property to composition of the present invention.
Below polyisocyanate compound (B1) is described.
, so long as getting final product, the compound that has 2 above isocyanate group at intramolecularly limits especially as the polyisocyanate compound (B1) of curable resin (B).
For example can enumerate 2,4-tolylene diisocyanate (2,4-TDI), 2,6-tolylene diisocyanate (2,6-TDI), 4,4 '-diphenylmethanediisocyanate (4,4 '-MDI), 2,4 '-diphenylmethanediisocyanate (2,4 '-MDI), 1,4-phenylene vulcabond, xylylene diisocyanate (XDI), tetramethyl-xylylene diisocyanate (TMXDI), tolidine vulcabond (TODI), l,5 naphthylene diisocyanate aromatic diisocyanates such as (NDI); Hexamethylene diisocyanate (HDI), trimethyl hexamethylene diisocyanate (TMHDI), 2,6-diaminocaproic acid vulcabond (lysine diisocyanate), norbornane two isocyanic acid methyl ester aliphatic diisocyanates such as (NBDI); Trans cyclohexane-1,4 vulcabond, isophorone diisocyanate (IPDI), H
6XDI (hydrogenation XDI), H
12MDI (hydrogenation MDI), H
6TDI ester ring type vulcabond such as (hydrogenation TDI) etc.
In addition, as polyisocyanate compound (B1), preferably use isocyanuric acid ester type polyisocyanates, adduction (adduct) type polyisocyanates.
Isocyanuric acid ester type polyisocyanates as polyisocyanate compound (B1) is the compound of representing with following formula (5).In the present invention, when containing isocyanuric acid ester type polyisocyanates, film-forming properties is good.Think that this is because the cause of isocyanurate ring cohesion.
In the formula, R
6Expression is removed the residue that isocyanate group forms by the diisocyanate cpd that has 2 isocyanate group at intramolecularly.In addition, a plurality of R
6Can be identical respectively, also can be different.
Constitute the diisocyanate cpd of isocyanuric acid ester type polyisocyanates so long as the compound that has 2 isocyanate group at intramolecularly get final product, qualification especially can be enumerated for example above-mentioned polyisocyanate compound.
Wherein, the viewpoint of, binding property good, appearance design excellence, preferred TDI, HDI, IPDI, TMXDI from the solidified nature of the composition that obtains.
As isocyanuric acid ester type polyisocyanates, can enumerate the isocyanurate trimer of mixing of IPDI isocyanurate trimer for example, HDI isocyanurate trimer, TDI isocyanurate trimer, TMXDI isocyanurate trimer, HDI and TDI.
As the commercially available product of isocyanuric acid ester type polyisocyanates, can enumerate for example HDI isocyanurate trimer (タ ケ ネ one ト D-170N, the military field of Mitsui ケ ミ カ Le ズ society system), HDI isocyanurate trimer (ス ミ ジ ュ one Le N3300, firmly change バ イ エ Le ウ レ タ Application society system), IPDI isocyanurate trimer (T1890, デ グ Star サ society system), HDI and TDI mix isocyanurate trimer (デ ス モ ジ ュ one Le L, firmly change バ イ エ Le ウ レ タ Application society system), HDI and TDI mix isocyanurate trimer (デ ス モ ジ ュ one Le HL, firmly change バ イ エ Le ウ レ タ Application society system).
In the present invention, the viscosity of isocyanuric acid ester type polyisocyanates is preferably 3,000～10,000mPas (cP), more preferably 4,000～8,000mPas (cP).When the scope of viscosity during in this scope, the film-forming properties of the present composition that obtains is better.
As polyisocyanate compound (B1) add the mould assembly polyisocyanates, be the compound that has 3 above isocyanate group and amino-formate bond at intramolecularly respectively.
In the present invention, when containing when adding the mould assembly polyisocyanates, composition and plastic molded article, particularly with the fusible engineering plastics of difficulty as the surface of the plastic molded article of principal constituent and metal evaporation film, the binding property excellence of filming.This is owing to add the mould assembly polyisocyanates and not only have the isocyanate group more than 3 but also have amino-formate bond more than 3 at intramolecularly, so the cross-linking density after composition solidifies improves, can form firm three dimensional network ocular structure.
As adding the mould assembly polyisocyanates, can enumerate low molecular polylol class for example shown below and above-mentioned shown in the affixture of diisocyanate cpd.
As the low molecular polylol class, can enumerate for example ethylene glycol (EG), glycol ether, propylene glycol (PG), dipropylene glycol, (1,3-or 1,4-) butyleneglycol, pentanediol, neopentyl glycol, hexylene glycol, cyclohexanedimethanol, glycerine, 1,1,1-TriMethylolPropane(TMP) (TMP), 1,2, low molecular polylols such as 5-hexanetriol, tetramethylolmethane; Carbohydrates such as Sorbitol Powder etc.
In these compounds, the viewpoint good from the solidified nature of the present composition that obtains, that binding property is excellent more, hardness of film is also excellent, preferred TMP.
As adding the mould assembly polyisocyanates, can enumerate the TMP adducts of for example using following formula (6) expression, more specifically, for example can enumerate by TMP and IPDI synthetic IPDITMP adducts, by TMP and TMXDI synthetic TMXDITMP adducts, by TMP and HDI synthetic HDITMP adducts, by TMP and TDI synthetic TDITMP adducts etc.
In the formula, R
7Expression is removed the residue that isocyanate group forms by the diisocyanate cpd that has 2 isocyanate group at intramolecularly.In addition, a plurality of R
7Can be identical respectively, also can be different.
As the commercially available product that adds the mould assembly polyisocyanates, can enumerate for example IPDITMP adducts (D140N, Mitsui Chemicals Port リ ウ レ タ Application society system), TMXDITMP adducts (サ イ セ Application 3174, Japanese サ イ テ Star Network イ Application ダ ス ト リ one ズ society system), HDITMP adducts (D160N, Mitsui Chemicals Port リ ウ レ タ Application society system), TDITMP adducts (ス ミ ジ ュ one Le L75, バ イ エ Le society system), XDITMP adducts (タ ケ ネ one ト D-120N, Mitsui Chemicals Port リ ウ レ タ Application society system).
Adding the not necessarily complete affixture of OH:NCO of mould assembly polyisocyanates, also can contain unreacting material, in addition, also can be the affixture of polyamine (for example diethylenetriamine, diethylenetriamine etc.) and diisocyanate cpd.
Polyisocyanate compound (B1) can use separately respectively or will be used in combination more than 2 kinds.
When using polyisocyanate compound (B1) as curable resin (B), composition of the present invention is preferred and then contain aromatics (C), and this aromatics (C) is to have the aromatics of hydroxyl and hydroxyl aliphatics or the ester ring type alkyl by divalent to be combined on the aromatic nucleus.
Aromatics (C) limits especially so long as have hydroxyl and compound that the aliphatics or the ester ring type alkyl of hydroxyl by divalent is combined on the aromatic nucleus gets final product, and also can have other the hydroxyl that directly is combined on the aromatic nucleus.
As its object lesson, preferably enumerate compound with following formula (7) expression.
In the formula, R
8The expression carbonatoms is 1～10 divalent aliphatics or ester ring type alkyl, R
9Expression hydrogen atom or carbonatoms are 1～10 1 valency alkyl, and p represents 1～3 integer.When p is 2 or 3, a plurality of R
8Can distinguish identical also can be different.
As R
8Carbonatoms be 1～10 divalent aliphatics or ester ring type alkyl, can enumerate for example aliphatic alkyl of divalent such as alkylidene group, vinylene; 1, the ester ring type alkyl of divalents such as 4-cyclohexylidene; And their combination group.More specifically, as alkylidene group, can for example preferably enumerate ethylidene, trimethylene, tetramethylene, octamethylene etc.
In addition, as R
9Carbonatoms be 1～10 1 valency alkyl, can enumerate for example 1 valency aliphatic alkyl of alkyl, vinyl, allyl group etc.; 1 valency ester ring type alkyl of cyclohexyl etc.; 1 valency aromatic hydrocarbyl of phenyl etc.; With group that these moiety combinations are got up etc.More specifically, as alkyl, preferably enumerate methyl, ethyl, n-propyl, normal-butyl, n-octyl etc.
R wherein
9Be preferably allyl group.
As aromatics (C), consider it is preferred with the compound that following formula (2), following formula (8) are represented from the angle of the easiness of raw material acquisition, the angle consideration excellent more from weather resistance, water tolerance excellence, the binding property of composition is preferred.
As aromatics (C),, can use the メ チ ロ Application 75-108 of OxyChem society system, the ス ミ ラ イ ト 23 of Sumitomo Chemical society system etc. as commercially available product.
In the following formula, n and q represent 1～3 integer respectively.
In the present invention, when using aromatics (C), the binding property of the composition that obtains is excellent more.The amino-formate bond that above-mentioned hydroxyl and isocyanic ester radical reaction are generated in aromatic nucleus, hydroxyl and the composition of aromatics (C) is with metal, the interactional cause of generation of filming.When particularly stating the compound shown in the formula (2) in the use as aromatics (C), with the Sauerstoffatom of aromatic nucleus Direct Bonding also with metal, be coated with membrane interaction, therefore make binding property more excellent.
Aromatics (C) can use separately respectively or will be used in combination more than 2 kinds.
It is 1.1～3.0 amount, more preferably 1.5～2.0 that the content of aromatics (C) preferably makes the equivalence ratio (NCO/OH) of the hydroxyl of the isocyanate group of polyisocyanate compound (B1) and aromatics (C).When the content of aromatics (C) during in this scope, the binding property of the composition that obtains is excellent more.
Below light solidified acrylic resin (B2) is described.
As the light solidified acrylic resin (B2) of curable resin (B),, limit especially so long as the compound that can solidified has (methyl) acryl by light gets final product.
Can enumerate and for example in 1 molecule, have 1 above carboxyl (COOH) with 1 or 2 (methyl) acryloxy (CH
2=CR-COO-, R:H or-CH
3) compound (below, be called compound (b1)), in 1 molecule, have the compound (below, be called compound (b2)) of (methyl) acryloxy more than 3.
As a kind of optimal way, compound (b1) can be set forth in the compound that end has carboxyl.
Excellent more from binding property, with the viewpoint of the intermiscibility excellence of resin, the number of carboxyl preferably has 1～3 in compound (b1).
The number of (methyl) acryloxy in 1 molecular compound (b1) is 1 or 2.From the excellent more viewpoint of binding property, appearance design, the number of (methyl) acryloxy preferably has 2 in 1 molecular compound (b1).
As compound (b1), can enumerate for example resultant of reaction, ω-carboxyl polycaprolactone list (methyl) acrylate, (methyl) acrylic acid dimer of hydroxyl (methyl) acrylate and polyprotonic acid and/or its acid anhydrides.
Reaction to hydroxyl (methyl) acrylate and polyprotonic acid and/or its acid anhydrides does not limit especially, for example can enumerate known method at present.
As the polyprotonic acid and/or its acid anhydrides that use when hydroxyl (methyl) acrylate and polyprotonic acid and/or its anhydride reaction, can enumerate for example succsinic acid, toxilic acid, phthalic acid, m-phthalic acid, terephthalic acid, sebacic acid, hexanodioic acid, nonane diacid, pentanedioic acid, suberic acid, propanedioic acid, tetrahydrophthalic acid, hexahydro-phthalic acid, Tetra hydro Phthalic anhydride, tetrahydronaphthalic anhydride, maleic anhydride, methylhexahydrophthalic acid, the methyltetrahydro phthalic acid, methyl hexahydro phthalic anhydride, methyltetrahydro Tetra hydro Phthalic anhydride etc., and their mixture.
As hydroxyl (methyl) acrylate that uses when hydroxyl (methyl) acrylate and polyprotonic acid and/or its anhydride reaction, for example can enumerate (methyl) 2-Hydroxy ethyl acrylate, (methyl) vinylformic acid-2-hydroxy propyl ester, vinylformic acid-2-hydroxyl butyl ester, (methyl) vinylformic acid-2-hydroxyl-3-phenoxy group propyl ester, glycerine list (methyl) acrylate, tetramethylolmethane list (methyl) acrylate etc. and their mixture.
As the compound (b1) that the reaction that utilizes polyprotonic acid and/or its acid anhydrides and hydroxyl (methyl) acrylate obtains, can enumerate for example by (methyl) vinylformic acid-2-hydroxy propyl ester and tetrahydronaphthalic anhydride synthetic 2-(methyl) acryloxy propyl group list tetrahydrophthalic acid ester etc.
Can enumerate the compound of for example using following formula (10) expression as ω-carboxyl polycaprolactone list (methyl) acrylate of compound (b1).
In addition, as compound (b1), can enumerate for example compound of two (methyl) vinylformic acid tripropylene glycol ester, two (methyl) vinylformic acid tristane diformazan alcohol ester, usefulness following formula (9), formula (10) expression.
In formula (9), m is 0～10 integer.When in this scope, because the increase of carboxylic acid acid value, so binding property is excellent more.Consider that from the angle that binding property is excellent more m is preferably 0 or 1.
Compound (b1) is considered from the angle of the easiness of binding property, raw material supply, preferred two (methyl) vinylformic acid tripropylene glycol ester, two (methyl) vinylformic acid tristane diformazan alcohol ester, the compound of using formula (9), formula (10) to represent, more preferably two (methyl) vinylformic acid tripropylene glycol ester, two (methyl) vinylformic acid tristane diformazan alcohol ester.
As the commercially available product of two (methyl) vinylformic acid tripropylene glycol ester, can enumerate for example M-220 (the synthetic society in East Asia system).
As the commercially available product of two (methyl) vinylformic acid tristane diformazan alcohol ester, can enumerate for example NK エ ス テ Le A-DCP (Xin Zhong village chemical industry society system).
With the m of formula (9) expression 0 compound (vinylformic acid) and the m that represents with formula (9) is that the mixture of 1 compound can be used as commercially available product and obtains.Such commercially available product can be enumerated for example M-5600 of the synthetic society in East Asia system.
Can be used as commercially available product with the compound of formula (10) expression obtains.Such commercially available product can be enumerated for example M-5400, the HOA-MPL of chemistry society of common prosperity society system of the synthetic society in East Asia system.
Above-claimed cpd (b2) gets final product qualification especially so long as have the compound of (methyl) acryloxy more than 3 in 1 molecule.
As the compound (b2-1) that in 1 molecule, has 3 (methyl) acryloxies, can enumerate for example trimethylolpropane tris (methyl) acrylate, tetramethylolmethane three (methyl) acrylate, Dipentaerythritol three (methyl) acrylate.
As the compound (b2-2) that in 1 molecule, has 4 (methyl) acryloxies, can enumerate for example tetramethylolmethane four (methyl) acrylate, Dipentaerythritol four (methyl) acrylate, tripentaerythritol four (methyl) acrylate.
As the compound (b2-3) that in 1 molecule, has (methyl) acryloxy more than 5, can enumerate compound, Dipentaerythritol five (methyl) acrylate, Dipentaerythritol six (methyl) acrylate, tripentaerythritol five (methyl) acrylate, tripentaerythritol six (methyl) acrylate, tripentaerythritol seven (methyl) acrylate, tripentaerythritol eight (methyl) acrylate of for example using following formula (11) expression.
Wherein, solidity, the hardness of filming, water tolerance, solvent resistance, chemical-resistant viewpoint are set out rapidly, preferably use the Viscoat 295 of following formula (11) expression, with the tetramethylol methane tetraacrylate of following formula (12) expression, with compound, Dipentaerythritol four (methyl) acrylate of following formula (13) expression.
As the commercially available product of the Viscoat 295 of representing with formula (11), can enumerate for example M-309 (the synthetic society in East Asia system), ラ イ ト ア Network リ レ one ト TMP-A (chemistry society of common prosperity society system), Ebecryl TEMPT (ダ イ セ Le サ イ テ Star Network society system), NK エ ス テ Le A-TMPT (Xin Zhong village chemical industry society system).
As the tetramethylol methane tetraacrylate of formula (12) expression, can enumerate for example M-450 (the synthetic society in East Asia system), ラ イ ト ア Network リ レ one ト PE-4A (chemistry society of common prosperity society system), EbecrylPETAK (ダ イ セ Le サ イ テ Star Network society system), NK エ ス テ Le ATMMT (Xin Zhong village chemical industry society system).
As the commercially available product that contains useful formula (13) expression dipentaerythritol acrylate, can enumerate for example M-402 (the synthetic society in East Asia system), ラ イ ト ア Network リ レ one ト DPE-6A (chemistry society of common prosperity society system), Ebecryl DDHA (ダ イ セ Le サ イ テ Star Network society system), NK エ ス テ Le A-PPH (Xin Zhong village chemical industry society system).
Light solidified acrylic resin (B2) can use separately respectively or will be used in combination more than 2 kinds.
When using light solidified acrylic resin (B2) as curable resin (B), composition of the present invention is preferred and then contain Photoepolymerizationinitiater initiater (D).
As Photoepolymerizationinitiater initiater (D), can enumerate the such carbonyl compound of methyl phenyl ketone based compound for example, bitter almond oil camphor based compound, benzophenone based compound, sulphur compound, azo-compound, peroxide compound, phosphine oxide based compound etc.More specifically, for example can enumerate bitter almond oil camphor, benzoin methyl ether, bitter almond oil camphor ethyl ether, bitter almond oil camphor isopropyl ether, acetoin, butyroin, toluene acyloin (toluoin), benzil, benzophenone, to methoxyl group benzophenone, diethoxy acetophenone, α, alpha, alpha-dimethyl oxygen base-α-phenyl methyl phenyl ketone, oxoethanoic acid methyl phenyl ester, oxoethanoic acid ethyl phenyl ester, 4,4 '-two (dimethylamino benzophenone), 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone, with the carbonyl compound of the 1-hydroxycyclohexylphenylketone of following formula (14) expression etc.; The sulphur compound of tetramethylthiuram monosulfide, tetramethyl-thiuram disulfide etc.; Diisopropyl azodicarboxylate, azo are two-2, the azo-compound of 4-methyl pentane nitrile etc.; The peroxide compound of benzoyl peroxide, ditertiary butyl peroxide etc.
In these polymerization starters, consider preferred 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone, 1-[4-(2-hydroxyl-oxethyl)-phenyl from the aspect of light stability, light cracked efficientibility, surface cure, intermiscibility, low volatilization, low odor with resin]-2-hydroxy-2-methyl-1-propane-1-ketone.
As the commercially available product of 1-hydroxycyclohexylphenylketone, can enumerate for example イ Le ガ キ ュ ア 184 (チ バ ス ペ シ ヤ リ テ イ ケ ミ カ Le ズ society system).
Photoepolymerizationinitiater initiater (D) can use separately respectively or will be used in combination more than 2 kinds.
The content of Photoepolymerizationinitiater initiater (D) is with respect to the above-mentioned light solidified acrylic resin (B2) of 100 mass parts, is preferably 1～10 mass parts, 2～8 mass parts more preferably.
Below Resins, epoxy (B3) is described.
Resins, epoxy (B3) as curable resin (B) gets final product so long as have the compound of epoxy group(ing), does not limit especially.
As Resins, epoxy (B3), can enumerate the polyphenol and the Epicholorohydrin that for example utilize dihydroxyphenyl propane, Bisphenol F, bisphenol S, six hydrogen dihydroxyphenyl propanes, tetramethyl-dihydroxyphenyl propane, pyrocatechol, Resorcinol, cresols phenolic varnish, tetrabromo-bisphenol, trihydroxy-biphenyl, two Resorcinol, bis-phenol Perfluoroacetone, tetramethyl-Bisphenol F, bis-xylene phenol, dihydroxy naphthlene etc. and react the glycidyl ether type that obtains; Utilize the aliphatic polyol of glycerine, neopentyl glycol, ethylene glycol, propylene glycol, butyleneglycol, hexylene glycol, polyoxyethylene glycol, polypropylene glycol etc. and the polyglycidyl ether that the Epicholorohydrin reaction obtains; The Racemic glycidol ether-ether type that utilizes the reaction of the hydroxycarboxylic acid of P-hydroxybenzoic acid, β-Qiang Jinaijiasuan etc. and Epicholorohydrin to obtain; Many glycidyl ester types of deriving and forming by the poly carboxylic acid of phthalic acid, methylphthalic acid, m-phthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, interior methyne tetrahydrophthalic acid, interior methyne hexahydrophthalic acid, trimellitic acid, polymerized fatty acid etc.; By deutero-glycidyl-amino glycidyl ether types such as amino-phenol, aminoalkyl group phenol; By benzaminic acid deutero-glycidyl-amino glycidyl ester type; By aniline, Tolylamine, bromamide, benzene dimethylamine, diamino-cyclohexane, two amino methyl hexanaphthene, 4,4 '-diaminodiphenyl-methane, 4,4 '-glycidyl group amine type that diamino diphenyl sulfone etc. is derived and formed; Epoxidation polyolefine, glycidyl glycolylurea, glycidyl alkyl hydantoin, isocyanuric acid triglycidyl group ester etc.
Wherein, consider preferred bisphenol A type epoxy resin, bisphenol f type epoxy resin from the aspect that the physical properties balance of easy acquisition and cured article is good.
Resins, epoxy (B3) can use separately respectively or will be used in combination more than 2 kinds.
When using Resins, epoxy (B3) as curable resin (B), composition of the present invention is preferred and then contain the solidifying agent (E) of Resins, epoxy (B3).
As solidifying agent (E), can enumerate for example amine compound, acid anhydrides based compound, acid amides based compound, phenol system compound, mercaptan based compound, imidazoles, 3 boron fluorides-amine coordination compound, guanidine derivative, ketimine compound.
Wherein, preferred amines based compound, ketimine compound.
As amine compound, can enumerate for example m-xylene diamine (MXDA), 1, the two amino methyl hexanaphthenes of 3-(1,3-BAC), the amine compound of norbornane diamines (NBDA), diaminodiphenyl-methane, diethylenetriamine, Triethylenetetramine (TETA), tetren, diamino diphenyl sulfone, isophorone diamine (IPDA), Dyhard RU 100, dimethyl benzyl amine, ketimine compound etc., synthesize the polyamine of the polyamide backbone that obtains etc. by linolenic acid dimer and quadrol.
Wherein, m-xylene diamine (MXDA), 1, (1,3-BAC), norbornane diamines (NBDA), Triethylenetetramine (TETA) etc. at room temperature be aqueous, the aspect consideration also high from good operability, solidified nature is preferred to the two amino methyl hexanaphthenes of 3-.
Solidifying agent (E) is preferably ketimine compound from the aspect of operability excellence.
As ketimine compound, can enumerate the latent curing agent that above-mentioned amine compound and reactive ketone are obtained.
Specifically, the ketimine compound of for example preferably enumerating the ketimine compound that obtains by norbornane diamines and isopropyl methyl reactive ketone, obtaining by m-xylene diamine and isopropyl methyl reactive ketone with following formula (16) expression with following formula (15) expression, by using of obtaining of m-xylene diamine and the metacetone reaction ketimine compound that following formula (17) represents, by 1, the ketimine compound that the 3-pair of amino methyl hexanaphthene and isopropyl methyl reactive ketone obtain.
Ketimine compound for example can by solvent-free down or exist under the condition of benzene,toluene,xylene equal solvent ketone and polyamine carries out reflux and utilize azeotropic to remove the water of disengaging, it is reacted obtains.
Solidifying agent (E) can use separately respectively or will be used in combination more than 2 kinds.
The usage quantity of solidifying agent (E) is with respect to 1 equivalent of the epoxy group(ing) in the composition, is preferably 0.8～1.1 equivalent, more preferably 0.95～1.05 equivalent.
Consider that from the viewpoint that binding property and appearance design are excellent more the content of curable resin (B) is with respect to the multipolymer (A) of 100 mass parts, be preferably 5～1,000 mass parts, more preferably 10～500 mass parts and then preferred 50～100 mass parts.
Composition of the present invention from the operability excellence, can improve the aspect of the appearance design of filming that obtains more, preferred and then contain solvent.
As solvent, can enumerate for example ethanol, Virahol, butanols, toluene, dimethylbenzene, acetone, methyl ethyl ketone, ethyl acetate, butylacetate etc.
Composition of the present invention can contain various additives, for example weighting agent, antiaging agent, static inhibitor, fire retardant, tackifier, dispersion agent, antioxidant, defoamer, flow agent, the agent of frosting, photostabilizer (for example, hindered amine based compound etc.), dyestuff, pigment etc. under the scope of not damaging the object of the invention.
As weighting agent, for example can enumerate agalmatolite clay, kaolin, burn till clay; Pyrogenic silica, burn till silicon-dioxide, sedimentation silicon-dioxide, pulverize silicon-dioxide, fused silica; Diatomite; Ferric oxide, zinc oxide, titanium oxide, barium oxide, magnesium oxide; Lime carbonate, magnesiumcarbonate, zinc carbonate; Organic or inorganic weighting agents such as carbon black; Their lipid acid, resinous acid, fatty acid ester handled thing, fatty acid ester urethanes handled thing.
As antiaging agent, for example can list hindered phenol compound, hindered amine compound.
As antioxidant, for example can list butylhydroxy toluene (BHT), butyl hydroxyanisole (BHA).
As antistatic agent, for example can list quaternary ammonium salt; Hydrophilic compounds such as polyoxyethylene glycol, epoxyethane derivative.
As fire retardant, for example can list chloroalkyl phosphate esters, dimethyl methyl phosphonate, bromine phosphorus compound, ammonium polyphosphate, neo-pentyl bromo-polyethers, bromination polyethers.
As tackifier, can enumerate for example terpine resin, phenol resins, terpene-phenol resin, Gum Rosin, xylene resin, Resins, epoxy.
As flow agent, can enumerate for example siloxane-based flow agent, acrylic acid series flow agent, ethene base system flow agent, fluorine is flow agent etc.
The manufacture method of composition of the present invention is limited especially, can use for example in reaction vessel, add above-mentioned each must composition and arbitrarily composition, under reduced pressure the stirrer with mixed milling machine etc. carries out abundant mixing method.
It is excellent filming that composition of the present invention can provide the binding property of difficult resin of binding property and appearance design.
Composition of the present invention for example can be used as, and paint base composition, frosting protective material, hard paint, UV curable paint wait and use.
Composition of the present invention goes for plastics, wherein under the situation of the difficult resin of binding property of reply, can bring into play the effect of binding property and appearance design excellence.
As the difficult resin of binding property of applicable composition of the present invention, can enumerate for example plexiglass, polycarbonate resin, polystyrene resin, the styrene copolymerized resin of vinyl cyanide, polyvinyl chloride (PVC) RESINS, acetate resin, ABS resin, vibrin, polyamide resin etc.
Do not limit especially being coated with method for compositions of the present invention, can adopt known coating processes such as for example brushing, flow coat, dip-coating, spraying, spin coating.
As the glue spread of composition of the present invention, preferably making the thickness of filming when solidifying is the such amount of 1～30 μ m.When the thickness of cured coating film is 1 μ m when above, particularly as the frosting deterioration of base material prevent the effect excellence, more excellent when being 30 μ m when following with the binding property of base material, can prevent fissured generation.
The curing of composition of the present invention can be enumerated and for example utilize hot curing, utilize ultraviolet curing according to the suitably selections such as kind of the curable resin (B) that uses in the present invention.
After composition of the present invention is solidified, on the cured article of composition of the present invention, can form metal level.
The method that forms metal level is limited especially, can enumerate the coating that for example carries out metal evaporation or will contain metal and be coated with the method that forms metal level.
The metal that uses in metal evaporation is not limited especially, can enumerate for example tin, aluminium, nickel, copper, indium etc.
Method to metal evaporation does not limit especially, can adopt known method.
Be used to form the coating of metal level so long as contain the coating of metal and get final product, limit especially, can use present known coating.
Composition of the present invention can be firmly bonding with difficult resin of binding property.In addition, the cured article of composition of the present invention, its surface smoothing and appearance design excellence.
Embodiment
Below, specifically describe the present invention by embodiment.But the present invention is not limited to these embodiment.
1. multipolymer (A) is synthetic
Each monomer component shown in the following table 1 is mixed with the mass ratio shown in the table 1, and in the presence of polymerization starter (AIBN (Diisopropyl azodicarboxylate)), in methyl ethyl ketone, make its polymerization, the multipolymer shown in the table 1 (A)-1～11 is obtained as methyl ethyl ketone (MEK) solution that the ratio with 30 quality % contains each multipolymer (A).
Table 1
| Table 1 | ||||||||||||
| Multipolymer (A) | ?-1 | ?-2 | ?-3 | ?-4 | ?-5 | ?-6 | ?-7 | ?-8 | ?-9 | ?-10 | ?-11 | |
| (methyl) alkyl acrylate (a1) | -1-2 | ?60 | ?40 | ?60 | ?60 | ?60 | ?60 | ?60 | ?100 | ?50 | ?50 | |
| (methyl) acrylamide monomer (a2) | -1-2-3-4 | ?20 | ?30 | ?20 | ?20 | ?20 | ?20 | ?20 | ?50 | ?50 | ||
| Vinyl monomer (a3) | -1-2 | ?20 | ?30 | ?20 | ?20 | ?20 | ?20 | ?20 | ?50 | ?50 | ||
The detailed content of the composition shown in the table 1 is as follows.
(methyl) alkyl acrylate (a1)-1: methyl methacrylate
(methyl) alkyl acrylate (a1)-2: butyl methacrylate
(methyl) acrylamide monomer (a2)-1:N-methoxyl group propylene acid amides (MRC ュ ニ テ Star Network society system)
(methyl) acrylamide monomer (a2)-2:N-isobutoxy acrylamide (MRC ュ ニ テ Star Network society system)
(methyl) acrylamide monomer (a2)-3: dimethylaminopropyl Methacrylamide (MRC ュ ニ テ Star Network society system)
(methyl) acrylamide monomer (a2)-4:N-butoxymethyl acrylamide (MRC ュ ニ テ Star Network society system)
Vinyl monomer (a3)-1: methacrylic acid
Vinyl monomer (a3)-2: acryloxy ethyl phthalic acid (the synthetic society in East Asia system)
2. preparation of compositions
Use stirrer that each composition shown in the following table 2 is mixed with the composition shown in the table 2 (mass parts), obtain each composition shown in the table 2.
3. evaluation method
The binding property and the appearance design of each composition that obtains by following method evaluation.
The results are shown in following table 2.
(1) binding property
Fusible evaluation is undertaken by the checker belt stripping test.
Specifically, each composition that at first will obtain is coated on the ABS resin (サ イ コ ラ Star Network, UMG ABS society system, below same), it is solidified make the test body.Composition for embodiment 9～10 and comparative example 4, after carrying out 3 minutes warm air drying under the back 50 ℃ condition of coating, GS UV SYSTEM with Japanese battery society system is that 1200mJ comes irradiation ultraviolet radiation like this with the accumulative total light quantity, for embodiment 1～8,11,12 and comparative example 1～3,5～7, under 80 ℃, carry out 30 minutes heating.
Then, on the test body that obtains, make 100 of the checkers (10 * 10) of 1mm, make glassine paper adhesive tape (width 18mm) fully attached on the checker, immediately an end of adhesive tape was peeled off in the state following moment that keeps the right angle with respect to ABS resin, research is not peeled off and the tessellated number that left behind fully.
(2) appearance design
For the evaluation of appearance design, each composition that uses atomizer to obtain is coated on the coated face ABS resin in vertical state, obtains sample.
After the spraying coating, will obtain the coated face horizontal positioned of sample, be 45 ° the angle sample that detects by an unaided eye from coated face with respect to sample.
For the judgement criteria of appearance design, note is done " zero " when coated face is level and smooth, and note is made " △ " when some convex-concave a little, and note is done " * " when convex-concave is obvious.
Table 2
| One of table 2 () | |||||||||||||
| Embodiment | |||||||||||||
| 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | ||
| Multipolymer (A) (30 quality % MEK solution) | -1 -2 -3 -4 -5 -6 -7 -8 -9 -10 -11 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
| Polyisocyanates (B1) | -1 -2 | 60 | 60 | 60 | 60 | 60 | 60 | 60 | 60 | ||||
| Aromatics (C) | 25 | 25 | 25 | 25 | 25 | 25 | 25 | 25 | |||||
| Light solidified acrylic resin (B2) | -1 -2 -3 | 35 20 10 | 35 20 10 | ||||||||||
| Photoepolymerizationinitiater initiater (D) | 5 | 5 | |||||||||||
| Resins, epoxy (B3) | -1 -2 | 50 | 50 | ||||||||||
| Solidifying agent (E) | 20 | 20 | |||||||||||
| Solvent | 315 | 315 | 315 | 315 | 315 | 315 | 165 | 315 | 330 | 330 | 330 | 330 | |
| Admittedly form subtotaling | 100 500 | 100 500 | 100 500 | 100 500 | 100 500 | 100 500 | 70 350 | 100 500 | 100 500 | 100 500 | 100 500 | 100 500 | |
| Binding property (individual/100) | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | |
| Appearance design | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | |
Table 2
| Table 2 (two) | ||||||||
| Comparative example | ||||||||
| 1 | 2 | 3 | 4 | 5 | ?6 | ?7 | ||
| Multipolymer (A) (30 quality %MEK solution) | -1-2-3-4-5-6-7-8-9-10-11 | 100 | 100 | 100 | 100 | 100 | ?333 | ?100 |
| Polyisocyanates (B1) | -1-2 | 60 | 60 | 60 | ?60 | |||
| Aromatics (C) | 25 | 25 | 25 | ?25 | ||||
| Light solidified acrylic resin (B2) | -1-2-3 | 35 20 10 | ||||||
| Photoepolymerizationinitiater initiater (D) | 5 | |||||||
| Resins, epoxy (B3) | -1-2 | 50 | ||||||
| Solidifying agent (E) | 20 | |||||||
| Solvent | 315 | 315 | 315 | 180 | 230 | ?167 | ?315 | |
| Admittedly form subtotaling | 100 500 | 100 500 | 100 500 | 70 350 | 100 500 | ?100?500 | ?100?500 | |
| Binding property (individual/100) | 100 | 100 | 100 | 100 | 100 | ?75 | ?100 | |
| Appearance design | × | × | × | △ | × | ?× | ?× | |
The detailed content of the composition shown in the table 2 is as follows.
Multipolymer (A)-1～11: preparation as described above
Polyisocyanate compound (B-1-1): IPDI isocyanuric acid ester, T1890, デ グ Star サ society system, 75 quality % ethyl acetate solutions
Polyisocyanate compound (B-1-2): TMXDI trimethylolpropane adduct, サ イ セ Application 3174, サ イ テ Star Network society system, 75 quality % ethyl acetate solutions
Aromatics (C): メ チ ロ Application 75-108, Oxy Chem society system
Light solidified acrylic resin (B2-1): M-309, the synthetic society in East Asia system
Light solidified acrylic resin (B2-2): M-220, the synthetic society in East Asia system
Light solidified acrylic resin (B2-3): NK エ ス テ Le A-DCP, Xin Zhong village chemical industry society system
Photoepolymerizationinitiater initiater (D): イ Le ガ キ ュ ア 184, チ バ ス ペ シ ヤ リ テ イ ケ ミ カ Le ズ society system
Resins, epoxy (B3-1): bisphenol A type epoxy resin, EP-4100, Xu Dianhuagongyeshe system
Resins, epoxy (B3-2): hydrogenation bisphenol A type epoxy resin, エ Port ラ イ ト 4000, chemistry society of common prosperity society system
Solidifying agent (E): the ketimine compound that norbornane diamines and methyl isopropyl Ketone (MIPK) reaction is obtained
Solvent: ethyl acetate, Northeast chemistry society system
From the result shown in the table 2 as can be known, composition (comparative example 6) appearance design, the poor adhesion that do not contain curable resin (B).Do not contain the composition (comparative example 1～5,7) of multipolymer (A), appearance design is low.
On the other hand, the composition of embodiment 1～12 has excellent binding property and appearance design to difficult resin of binding property.
Claims (9)
1. curable resin composition, it is characterized in that, contain multipolymer (A) and curable resin (B), described multipolymer (A) makes the monomer component that contains (methyl) alkyl acrylate (a1), (methyl) acrylamide monomer (a2) and have the vinyl monomer (a3) of carboxyl carry out polymerization and obtains, above-mentioned (methyl) acrylamide monomer (a2) is the compound with following formula (1) expression
CH
2＝CR
1-CO-NH-R
2 (1)
In the formula, R
1Be hydrogen atom or methyl, R
2Be saturated hydrocarbyl, ester ring type alkyl, aromatic hydrocarbyl, alkoxyl group, phenoxy group, have ehter bond alkyl, contain the alkyl of nitrogen-atoms or contain the alkyl of sulphur atom.
2. curable resin composition as claimed in claim 1, it is characterized in that the compound of representing with following formula (1) is at least a kind of compound that is selected from N-methoxyl group propylene acid amides, N-isobutoxy acrylamide, dimethylaminopropyl Methacrylamide and the N-butoxymethyl acrylamide.
3. curable resin composition as claimed in claim 1 or 2 is characterized in that, the weight-average molecular weight of above-mentioned multipolymer (A) is 10000～150000.
4. as each described curable resin composition of claim 1～3, it is characterized in that, in above-mentioned monomer component 100 mass parts of above-mentioned multipolymer (A), contain above-mentioned (methyl) alkyl acrylate (a1) of 20～90 mass parts, above-mentioned (methyl) the acrylamide monomer (a2) of 1～50 mass parts and the above-mentioned vinyl monomer (a3) of 1～50 mass parts.
5. as each described curable resin composition of claim 1～4, it is characterized in that the content of above-mentioned curable resin (B) is 1～1000 mass parts with respect to the above-mentioned multipolymer (A) of 100 mass parts.
6. as each described curable resin composition of claim 1～5, it is characterized in that above-mentioned curable resin (B) is polyisocyanate compound (B1),
Described curable resin composition and then contain aromatics (C), aromatics (C) is the aromatics with hydroxyl, above-mentioned hydroxyl is combined on the aromatic nucleus by the aliphatics or the ester ring type alkyl of divalent.
7. curable resin composition as claimed in claim 6 is characterized in that, above-mentioned aromatics (C) is the compound with following formula (7) expression,
In the formula, R
8The expression carbonatoms is 1～10 divalent aliphatics or ester ring type alkyl, R
9Expression hydrogen atom or carbonatoms are 1～10 1 valency alkyl, and p represents 1～3 integer, when p is 2 or 3, and a plurality of R
8Can distinguish identical also can be different.
8. as each described curable resin composition of claim 1～5, it is characterized in that above-mentioned curable resin (B) is light solidified acrylic resin (B2),
Described curable resin composition and then contain Photoepolymerizationinitiater initiater (D).
9. as each described curable resin composition of claim 1～5, it is characterized in that above-mentioned curable resin (B) is Resins, epoxy (B3),
Described curable resin composition and then contain the solidifying agent (E) of above-mentioned Resins, epoxy (B3).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP003659/2007 | 2007-01-11 | ||
| JP2007003659A JP4264108B2 (en) | 2007-01-11 | 2007-01-11 | Curable resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101220193A CN101220193A (en) | 2008-07-16 |
| CN101220193B true CN101220193B (en) | 2011-11-23 |
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ID=39630285
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008100034267A Expired - Fee Related CN101220193B (en) | 2007-01-11 | 2008-01-11 | Soldifiable resin composition |
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| Country | Link |
|---|---|
| JP (1) | JP4264108B2 (en) |
| CN (1) | CN101220193B (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104212220B (en) * | 2010-05-12 | 2016-06-22 | 大日本印刷株式会社 | Make the method for locally lying in hard conating of the polymer containing quaternary ammonium salt |
| JP5773087B2 (en) * | 2012-10-11 | 2015-09-02 | 横浜ゴム株式会社 | Water-based primer composition |
| KR102037558B1 (en) * | 2015-07-20 | 2019-10-28 | 주식회사 엘지화학 | An Ink Composition for 3D Printing Support and the Manufacturing Method using the Same |
| KR102053481B1 (en) * | 2015-11-03 | 2019-12-06 | 주식회사 엘지화학 | A forming method for three dimentional sculptures |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85107940A (en) * | 1984-10-29 | 1986-05-10 | B·F·谷德里奇公司 | Use the oil strainer of water-based latex binder |
| US4605476A (en) * | 1984-08-02 | 1986-08-12 | Ppg Industries, Inc. | Resinous blends of epoxy and acrylic resins and the use thereof in electrodeposition |
-
2007
- 2007-01-11 JP JP2007003659A patent/JP4264108B2/en not_active Expired - Fee Related
-
2008
- 2008-01-11 CN CN2008100034267A patent/CN101220193B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4605476A (en) * | 1984-08-02 | 1986-08-12 | Ppg Industries, Inc. | Resinous blends of epoxy and acrylic resins and the use thereof in electrodeposition |
| CN85107940A (en) * | 1984-10-29 | 1986-05-10 | B·F·谷德里奇公司 | Use the oil strainer of water-based latex binder |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101220193A (en) | 2008-07-16 |
| JP4264108B2 (en) | 2009-05-13 |
| JP2008169302A (en) | 2008-07-24 |
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