JPWO2011122197A1 - 活性エネルギー線硬化型樹脂組成物、その硬化物及びフィルム - Google Patents
活性エネルギー線硬化型樹脂組成物、その硬化物及びフィルム Download PDFInfo
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- JPWO2011122197A1 JPWO2011122197A1 JP2011548501A JP2011548501A JPWO2011122197A1 JP WO2011122197 A1 JPWO2011122197 A1 JP WO2011122197A1 JP 2011548501 A JP2011548501 A JP 2011548501A JP 2011548501 A JP2011548501 A JP 2011548501A JP WO2011122197 A1 JPWO2011122197 A1 JP WO2011122197A1
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- 239000011342 resin composition Substances 0.000 title claims abstract description 39
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 198
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 150000002009 diols Chemical class 0.000 claims abstract description 28
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 10
- -1 methacryloyl group Chemical group 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229920001451 polypropylene glycol Polymers 0.000 claims description 16
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- PDHFSBXFZGYBIP-UHFFFAOYSA-N 2-[2-(2-hydroxyethylsulfanyl)ethylsulfanyl]ethanol Chemical compound OCCSCCSCCO PDHFSBXFZGYBIP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- ZDNHCMQQCSOLIX-UHFFFAOYSA-N 1-[1-[2-(2-hydroxypropylsulfanyl)propylsulfanyl]propan-2-ylsulfanyl]propan-2-ol Chemical compound CC(O)CSC(C)CSCC(C)SCC(C)O ZDNHCMQQCSOLIX-UHFFFAOYSA-N 0.000 claims description 3
- DUFCZJRMDGJQRR-UHFFFAOYSA-N 2-(1-hydroxypropan-2-ylsulfanyl)propan-1-ol Chemical group OCC(C)SC(C)CO DUFCZJRMDGJQRR-UHFFFAOYSA-N 0.000 claims description 3
- DMRWIWTZZHAWHQ-UHFFFAOYSA-N 2-[1-[2-(2-hydroxyethylsulfanyl)propylsulfanyl]propan-2-ylsulfanyl]ethanol Chemical compound OCCSC(CSCC(SCCO)C)C DMRWIWTZZHAWHQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000000576 coating method Methods 0.000 abstract description 34
- 239000011248 coating agent Substances 0.000 abstract description 32
- 239000000203 mixture Substances 0.000 abstract description 24
- 239000012298 atmosphere Substances 0.000 abstract description 9
- 239000010410 layer Substances 0.000 description 28
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(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.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 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 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004386 Erythritol Substances 0.000 description 3
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 3
- 235000019414 erythritol Nutrition 0.000 description 3
- 229940009714 erythritol Drugs 0.000 description 3
- 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 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000011158 quantitative evaluation Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 3
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 3
- 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 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- WGLYLHNRGWWZMW-UHFFFAOYSA-N 1-(2-hydroxypropylsulfanyl)propan-2-ol Chemical compound CC(O)CSCC(C)O WGLYLHNRGWWZMW-UHFFFAOYSA-N 0.000 description 2
- DPGDWQDYDTUUFA-UHFFFAOYSA-N 1-[2-(2-hydroxybutylsulfanyl)ethylsulfanyl]butan-2-ol Chemical compound CCC(O)CSCCSCC(O)CC DPGDWQDYDTUUFA-UHFFFAOYSA-N 0.000 description 2
- TVJMNKFRSJHLBL-UHFFFAOYSA-N 1-[2-(2-hydroxypropylsulfanyl)ethylsulfanyl]propan-2-ol Chemical compound CC(O)CSCCSCC(C)O TVJMNKFRSJHLBL-UHFFFAOYSA-N 0.000 description 2
- XNKBUYFJNGMIRU-UHFFFAOYSA-N 1-[2-[2-(2-hydroxypropylsulfanyl)ethoxy]ethylsulfanyl]propan-2-ol Chemical compound CC(O)CSCCOCCSCC(C)O XNKBUYFJNGMIRU-UHFFFAOYSA-N 0.000 description 2
- BHEMISMYRYZVAA-UHFFFAOYSA-N 1-chloro-3-(2-hydroxyethylsulfanyl)propan-2-ol Chemical compound OCCSCC(O)CCl BHEMISMYRYZVAA-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- CZZVAVMGKRNEAT-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)CO.OCC(C)(C)C(O)=O CZZVAVMGKRNEAT-UHFFFAOYSA-N 0.000 description 2
- VZYIKHZFVOUXKE-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethylsulfanyl)ethylsulfanyl]ethylsulfanyl]ethanol Chemical compound OCCSCCSCCSCCO VZYIKHZFVOUXKE-UHFFFAOYSA-N 0.000 description 2
- NOOVYQOSAZFXKR-UHFFFAOYSA-N 2-[2-[2-[2-(2-hydroxyethylsulfanyl)ethoxy]ethylsulfanyl]ethoxy]ethanol Chemical compound OCCOCCSCCOCCSCCO NOOVYQOSAZFXKR-UHFFFAOYSA-N 0.000 description 2
- XKHKXVFJLCVBPV-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-hydroxyethylsulfanyl)ethoxy]ethylsulfanyl]ethoxy]ethylsulfanyl]ethanol Chemical compound OCCSCCOCCSCCOCCSCCO XKHKXVFJLCVBPV-UHFFFAOYSA-N 0.000 description 2
- JIJWGPUMOGBVMQ-UHFFFAOYSA-N 2-[3-(2-hydroxyethylsulfanyl)propylsulfanyl]ethanol Chemical compound OCCSCCCSCCO JIJWGPUMOGBVMQ-UHFFFAOYSA-N 0.000 description 2
- FORJWQPDKXQQOG-UHFFFAOYSA-N 2-[4-(2-hydroxyethylsulfanyl)butylsulfanyl]ethanol Chemical compound OCCSCCCCSCCO FORJWQPDKXQQOG-UHFFFAOYSA-N 0.000 description 2
- FCYBBCGIQPEFBH-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)-2-methylpropan-1-ol Chemical compound OCC(C)CSCCO FCYBBCGIQPEFBH-UHFFFAOYSA-N 0.000 description 2
- QRQVZZMTKYXEKC-UHFFFAOYSA-N 3-(3-hydroxypropylsulfanyl)propan-1-ol Chemical compound OCCCSCCCO QRQVZZMTKYXEKC-UHFFFAOYSA-N 0.000 description 2
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- GBZDOXLAUOJYPB-UHFFFAOYSA-N 3-[2-(3-hydroxypropylsulfanyl)ethylsulfanyl]propan-1-ol Chemical compound OCCCSCCSCCCO GBZDOXLAUOJYPB-UHFFFAOYSA-N 0.000 description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-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
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
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- 239000004793 Polystyrene Substances 0.000 description 2
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- 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 2
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- 238000001035 drying Methods 0.000 description 2
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- 230000020169 heat generation Effects 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 229920001748 polybutylene Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
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- OEYNWAWWSZUGDU-UHFFFAOYSA-N 1-methoxypropane-1,2-diol Chemical compound COC(O)C(C)O OEYNWAWWSZUGDU-UHFFFAOYSA-N 0.000 description 1
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- BXPKASQEUYICBF-UHFFFAOYSA-N 2-(3-prop-2-enoyloxypropoxycarbonyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCCCOC(=O)C=C BXPKASQEUYICBF-UHFFFAOYSA-N 0.000 description 1
- HHGMODSKOYEYJL-UHFFFAOYSA-N 2-(3-prop-2-enoyloxypropoxycarbonyl)cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC=CC1C(=O)OCCCOC(=O)C=C HHGMODSKOYEYJL-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
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- 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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- 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
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
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- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/28—Treatment by wave energy or particle radiation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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Abstract
Description
本発明で用いるウレタン(メタ)アクリレート(A)は、重量平均分子量(Mw)が500〜5,000の範囲であるポリアルキレングリコール(a1)と、アルキレンチオエーテル構造を分子構造内に有するジオール(a2)と、分子量が100〜500の範囲であるジイソシアネート(a3)と、分子構造中にヒドロキシル基を一つ有する(メタ)アクリレート(a4)とを必須の原料成分として反応させて得られるものである。
測定装置 ;東ソー株式会社製 HLC−8220GPC
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
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重量%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 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
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重量%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)
重量平均分子量(Mw)2,000のポリプロピレングリコールを4,000g(2モル)、1,2−ビス(2ヒドロキシエチルチオ)エタン91g(1モル)をフラスコに仕込み、さらに触媒としてオクタン酸スズ(II)とオクタン酸亜鉛(II)をそれぞれ200ppm、重合禁止剤としてジブチルヒドロキシトルエン3,000ppm、メトキノン300ppm、溶剤として酢酸ノルマルブチルをフラスコ内の固形分が80%となる量を加えよく混合し、系内の温度を50℃に調整した。その後、発熱に注意しながらトルエンジイソシアネート261g(3モル)を3分割して加え、80℃で1時間反応させた。更に、ヒドロキシプロピルアクリレート260g(2モル)を加え、空気を吹き込みながら80度でイソシアネート基が完全に消失するまで反応させ、重量平均分子量(Mw)24,000のウレタンアクリレート(A1)を得た。
第一表に示す原料及び配合量で合成を行う以外は合成例1と同様にしてウレタンアクリレート(A2)〜(A7)を得た。それぞれの重量平均分子量(Mw)の値を第一表に示す。
ポリアルキレングリコール1:重量平均分子量が2,000のポリプロピレングリコール
ポリアルキレングリコール2:重量平均分子量が1,000のポリプロピレングリコール
ポリアルキレングリコール3:重量平均分子量が4,000のポリプロピレングリコール
ポリアルキレングリコール4:重量平均分子量が700のポリプロピレングリコール
第二表に示す原料及び配合量で合成を行う以外は合成例1と同様にして比較対照用ウレタンアクリレート(a1)〜(a3)を得た。それぞれの重量平均分子量(Mw)と数平均分子量(Mn)の値を第二表に示す。
ポリアルキレングリコール5:重量平均分子量が400のポリプロピレングリコール
ポリアルキレングリコール6:重量平均分子量が8,000のポリプロピレングリコール
ポリアルキレングリコール7:重量平均分子量が2,000のポリプロピレングリコール
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(重量比60/40)535.5gをフラスコに仕込んだ。触媒としてオクタン酸スズ(II)とオクタン酸亜鉛(II)をそれぞれ200ppm、酸化防止剤としてジブチルヒドロキシトルエン3,000ppm、重合禁止剤としてメトキノン300ppmとなるようにフラスコに加え、更に酢酸ノルマルブチルを固形分が80%となるように混合し、系内の温度を50℃に調整した。
ウレタンアクリレート(A1)3g、ウレタンアクリレート(B1)48.5g、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の混合物(重量比40/60)48.5g、1−ヒドロキシシクロヘキシルフェニルケトン4g、酢酸ブチル104gを混合し、固形分量が50質量%の活性エネルギー線硬化型組成物(1)を得た。組成物(1)を用いて下記条件にてフィルム上にハードコート層を形成し、付着した指紋跡の目立ちにくさ及び付着した指紋跡の拭き取りやすさを下記基準に従って評価した。付着した指紋跡の目立ちにくさ及び付着した指紋跡の拭き取りやすさは、ハードコート層を形成した初期段階と指紋跡の付着と除去を20回繰り返した後の段階のそれぞれについて評価した。付着した指紋跡の除去は、後述する指紋跡の拭き取りやすさの評価方法で行った。尚、ウレタンアクリレート(B1)48.5g、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の混合物(重量比40/60)48.5gの混合物のアクリロイル当量は104g/molであった。
組成物(1)PETフィルム(125μm)に乾燥膜厚が5μmになるようにバーコーターを用いて塗工した。70℃で5分間溶剤を乾燥させた後、高圧水銀灯(80W/cm)で照射量が500mJ/cm2となるように紫外線を照射し、ハードコート層を得た。尚、紫外線の照射は空気雰囲気下もしくは窒素雰囲気下で行った。
指紋跡の目立ちにくさは視認角度で定量評価した。視認角度とは、ハードコート層に付着させた指紋跡に対する目視角度を90度から徐々に下げていき、指紋跡が確認され始める角度をいう。視認角度が小さいほど、指紋跡の目立ちにくさが良好である。
指紋跡の拭き取り易さは、指紋跡をハードコート層から除去する際のふき取り回数で評価した。具体的には、ハードコート層に付着させた指紋跡の上にティッシュペーパーを1Kg(5.7平方センチメートルあたり)で往復させ、付着した指紋跡が完全に見えなくなるまでの往復回数で定量評価した。この往復回数が少ないほど、指紋跡の拭取りやすさが良好である。
JIS K5600−5−4に準拠して鉛筆硬度測定を行った。1つの硬度につき5回測定を行い、4回以上傷がつかない硬度を硬化塗膜の有する硬度とした。
第三表及び第四表に示す配合で行う以外は実施例1と同様にして活性エネルギー線硬化型樹脂組成物2〜9及び比較対照用活性エネルギー線硬化型樹脂組成物1’〜3’を調製した。実施例1と同様の評価を行い、その結果を第五表〜第七表に示す。
多官能アクリレート(B2):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の混合物(重量比40/60)
多官能アクリレート(B1)と多官能アクリレート(B2)の混合物のアクリロイル基当量は104g/mol
光開始剤:1−ヒドロキシシクロヘキシルフェニルケトン
希釈溶剤:酢酸ノルマルブチル
重量平均分子量(Mw)2,000のポリプロピレングリコールを4,000g(2モル)、1,2−ビス(2ヒドロキシエチルチオ)エタン182g(1モル)をフラスコに仕込み、さらに触媒としてオクタン酸スズ(II)とオクタン酸亜鉛(II)をそれぞれ200ppm、重合禁止剤としてジブチルヒドロキシトルエン3,000ppm、メトキノン300ppm、溶剤として酢酸ノルマルブチルをフラスコ内の固形分が80%となる量を加えよく混合し、系内の温度を50℃に調整した。その後、発熱に注意しながらトルエンジイソシアネート696g(4モル)を3分割して加え、80℃で1時間反応させた。更に、ヒドロキシプロピルアクリレート260g(2モル)を加え、空気を吹き込みながら80度でイソシアネート基が完全に消失するまで反応させ、重量平均分子量(Mw)24,000のウレタンアクリレート(A1)を得た。
Claims (12)
- 重量平均分子量(Mw)が500〜5,000の範囲であるポリアルキレングリコール(a1)と、アルキレンチオエーテル構造を分子構造内に有するジオール(a2)と、分子量が500以下であるジイソシアネート(a3)と、分子構造中にヒドロキシル基を一つ有する(メタ)アクリレート(a4)とを必須の原料成分として反応させて得られる重量平均分子量(Mw)が10,000〜100,000の範囲であるウレタン(メタ)アクリレート(A)と、多官能(メタ)アクリレート(B)とを含有することを特徴とする活性エネルギー線硬化型樹脂組成物。
- 前記ポリアルキレングリコール(a1)がポリプロピレングリコールである請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記アルキレンチオエーテル構造を分子構造内に有するジオール(a2)が、2,2’−チオビス(1−プロパノール)、1,2−ビス(2−ヒドロキシエチルチオ)エタン、2−[2−[2−(2−ヒドロキシエチルチオ)プロピルチオ]−1−メチルエチルチオ]エタノール、1−(2−[2−(2−ヒドロキシプロピルスルファニル)プロピルスルファニル]1−メチル−エチルスルファニル)プロパン−2−オールからなる群から選ばれる1種類以上の化合物である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記ウレタン(メタ)アクリレート(A)の原料中のポリアルキレングリコール(a1)とアルキレンチオエーテル構造を分子構造内に有するジオール(a2)との含有量のモル比〔(a1)/(a2)〕が1/0.2〜1/5となる範囲である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記分子構造中にヒドロキシル基を一つ有する(メタ)アクリレート(a4)が、分子構造中にメタアクリロイル基を1つ有するモノヒドロキシモノ(メタ)アクリレートである請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記ウレタン(メタ)アクリレート(A)と多官能(メタ)アクリレート(B)との質量比〔(A)/(B)〕が0.1/99.9〜15/85の範囲である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記多官能(メタ)アクリレート(B)として、分子量が600未満であるモノマー型の多官能(メタ)アクリレート(b1)と分子量が600〜3,000の範囲であるオリゴマー型多官能(メタ)アクリレート(b2)とを併用することを特徴とする請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記分子量が600〜3,000の範囲であるオリゴマー型多官能(メタ)アクリレート(b2)が多官能ウレタン(メタ)アクリレートである請求項8記載の活性エネルギー線硬化型樹脂組成物。
- 前記分子量が600未満であるモノマー型の多官能(メタ)アクリレート(b1)と分子量が600〜3,000の範囲であるオリゴマー型多官能(メタ)アクリレート(b2)との質量比[(b1)/(b2)]が1/2〜2/1の範囲である請求項8記載の活性エネルギー線硬化型樹脂組成物。
- 請求項1〜10のいずれか1つに記載の活性エネルギー線硬化型樹脂組成物を硬化させてなることを特徴とする硬化物。
- 請求項1〜10のいずれか1つに記載の活性エネルギー線硬化型樹脂組成物を硬化させてなる硬化層をフィルム状基材上に有することを特徴とするフィルム。
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