JP7411639B2 - 合わせガラスの中間膜用変性ビニルアセタール樹脂 - Google Patents
合わせガラスの中間膜用変性ビニルアセタール樹脂 Download PDFInfo
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- JP7411639B2 JP7411639B2 JP2021509267A JP2021509267A JP7411639B2 JP 7411639 B2 JP7411639 B2 JP 7411639B2 JP 2021509267 A JP2021509267 A JP 2021509267A JP 2021509267 A JP2021509267 A JP 2021509267A JP 7411639 B2 JP7411639 B2 JP 7411639B2
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- acetal resin
- laminated glass
- ethylene
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- -1 Modified vinyl acetal resin Chemical compound 0.000 title claims description 98
- 229920006324 polyoxymethylene Polymers 0.000 title claims description 80
- 239000011354 acetal resin Substances 0.000 title claims description 78
- 239000005340 laminated glass Substances 0.000 title claims description 55
- 239000011229 interlayer Substances 0.000 title claims description 28
- 238000006359 acetalization reaction Methods 0.000 claims description 56
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 50
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 45
- 239000005977 Ethylene Substances 0.000 claims description 45
- 239000011521 glass Substances 0.000 claims description 38
- 229920005989 resin Polymers 0.000 claims description 26
- 239000011347 resin Substances 0.000 claims description 26
- 239000011342 resin composition Substances 0.000 claims description 26
- 239000004014 plasticizer Substances 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 description 39
- 239000000047 product Substances 0.000 description 27
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 24
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 20
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 15
- 230000035515 penetration Effects 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000010410 layer Substances 0.000 description 13
- 238000000465 moulding Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003963 antioxidant agent Substances 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 150000001241 acetals Chemical group 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 239000006096 absorbing agent Substances 0.000 description 8
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- 238000007127 saponification reaction Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CBECDWUDYQOTSW-UHFFFAOYSA-N 2-ethylbut-3-enal Chemical compound CCC(C=C)C=O CBECDWUDYQOTSW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000006087 Silane Coupling Agent Substances 0.000 description 6
- 239000005038 ethylene vinyl acetate Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 6
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 229920001567 vinyl ester resin Polymers 0.000 description 6
- FRQDZJMEHSJOPU-UHFFFAOYSA-N Triethylene glycol bis(2-ethylhexanoate) Chemical compound CCCCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CCCC FRQDZJMEHSJOPU-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
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- 150000001299 aldehydes Chemical class 0.000 description 5
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229920000554 ionomer Polymers 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000002530 phenolic antioxidant Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920005992 thermoplastic resin Polymers 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
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- 238000007254 oxidation reaction Methods 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 3
- 230000002087 whitening effect Effects 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
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- 239000000975 dye Substances 0.000 description 2
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- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
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- 239000000155 melt Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
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- 239000000758 substrate Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- YEYCMBWKTZNPDH-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) benzoate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)C1=CC=CC=C1 YEYCMBWKTZNPDH-UHFFFAOYSA-N 0.000 description 1
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- QYPLKDUOPJZROX-UHFFFAOYSA-N 2,2-dimethylbutanal Chemical compound CCC(C)(C)C=O QYPLKDUOPJZROX-UHFFFAOYSA-N 0.000 description 1
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 1
- CXDRHQMFHIESDS-UHFFFAOYSA-N 2,4-ditert-butyl-6-(5-chlorobenzotriazol-2-yl)-4-methylcyclohexa-1,5-dien-1-ol Chemical compound CC(C)(C)C1(C)CC(C(C)(C)C)=C(O)C(N2N=C3C=C(Cl)C=CC3=N2)=C1 CXDRHQMFHIESDS-UHFFFAOYSA-N 0.000 description 1
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 1
- WSOMHEOIWBKOPF-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CP2(=O)C3=CC=CC=C3C3=CC=CC=C3O2)=C1 WSOMHEOIWBKOPF-UHFFFAOYSA-N 0.000 description 1
- JRRSZPBVIHXNBS-UHFFFAOYSA-N 2-(2H-benzotriazol-4-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)c1ccc(O)c(c1)-c1cccc2[nH]nnc12 JRRSZPBVIHXNBS-UHFFFAOYSA-N 0.000 description 1
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 1
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 description 1
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
- MXALMAQOPWXPPY-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]prop-2-enoic acid Chemical compound CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O MXALMAQOPWXPPY-UHFFFAOYSA-N 0.000 description 1
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- AKNMPWVTPUHKCG-UHFFFAOYSA-N 2-cyclohexyl-6-[(3-cyclohexyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound OC=1C(C2CCCCC2)=CC(C)=CC=1CC(C=1O)=CC(C)=CC=1C1CCCCC1 AKNMPWVTPUHKCG-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 1
- GIUKAVFPFOMQTR-UHFFFAOYSA-N 3,3-bis[2-(2-hexoxyethoxy)ethyl]pentanedioic acid Chemical class C(CCCCC)OCCOCCC(CC(=O)O)(CC(=O)O)CCOCCOCCCCCC GIUKAVFPFOMQTR-UHFFFAOYSA-N 0.000 description 1
- PQCMNMXXZIXYBI-UHFFFAOYSA-N 3,4-bis(2-butoxyethyl)phthalic acid Chemical class CCCCOCCC1=CC=C(C(O)=O)C(C(O)=O)=C1CCOCCCC PQCMNMXXZIXYBI-UHFFFAOYSA-N 0.000 description 1
- MVXDXFQZKFQQGX-UHFFFAOYSA-N 3,4-bis[2-(2-butoxyethoxy)ethyl]phthalic acid Chemical class CCCCOCCOCCC1=CC=C(C(O)=O)C(C(O)=O)=C1CCOCCOCCCC MVXDXFQZKFQQGX-UHFFFAOYSA-N 0.000 description 1
- HRECPBLGWOTTIT-UHFFFAOYSA-N 3,9-bis(2-dodecylsulfanylethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane Chemical compound C1OC(CCSCCCCCCCCCCCC)OCC21COC(CCSCCCCCCCCCCCC)OC2 HRECPBLGWOTTIT-UHFFFAOYSA-N 0.000 description 1
- PRKMQTLVLAHFAW-UHFFFAOYSA-N 3-[1-(3,5-ditert-butyl-4-hydroxyphenyl)-2-methyl-4,4-bis(1,2,2,6,6-pentamethylpiperidin-4-yl)butan-2-yl]oxy-3-oxopropanoic acid Chemical compound C1C(C)(C)N(C)C(C)(C)CC1C(C1CC(C)(C)N(C)C(C)(C)C1)CC(C)(OC(=O)CC(O)=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PRKMQTLVLAHFAW-UHFFFAOYSA-N 0.000 description 1
- QRLSTWVLSWCGBT-UHFFFAOYSA-N 4-((4,6-bis(octylthio)-1,3,5-triazin-2-yl)amino)-2,6-di-tert-butylphenol Chemical class CCCCCCCCSC1=NC(SCCCCCCCC)=NC(NC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=N1 QRLSTWVLSWCGBT-UHFFFAOYSA-N 0.000 description 1
- PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 description 1
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
- ZNYCLBAKMDJFBC-UHFFFAOYSA-N 4-[[4,6-bis(octylsulfanyl)-1,3,5-triazin-2-yl]amino]-2,6-dimethylphenol Chemical class CCCCCCCCSC1=NC(SCCCCCCCC)=NC(NC=2C=C(C)C(O)=C(C)C=2)=N1 ZNYCLBAKMDJFBC-UHFFFAOYSA-N 0.000 description 1
- GSEQDFDCFJOCLZ-UHFFFAOYSA-N 4-[[4,6-bis(octylsulfanyl)-1,3,5-triazin-2-yl]amino]-2-tert-butyl-6-methylphenol Chemical class CCCCCCCCSC1=NC(SCCCCCCCC)=NC(NC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=N1 GSEQDFDCFJOCLZ-UHFFFAOYSA-N 0.000 description 1
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Images
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Description
本発明における変性ビニルアセタール樹脂は、酸性触媒の存在下において、エチレンを共重合させたビニルアルコール樹脂(以下、エチレンビニルアルコール共重合体という)とアルデヒドをアセタール化反応させて得られるものである。
変性ビニルアセタール樹脂を製造するための溶媒には、特に制限はないが、例えば、水、アルコール類、ジメチルスルホキシド、水とアルコール類の混合溶媒などが挙げられる。
で表される。
本発明の樹脂組成物は、変性ビニルアセタール樹脂を好ましくは80質量%以上(100%を含む)、より好ましくは90質量%以上(100%を含む)、さらに好ましくは95質量%以上(100%を含む)含有する。
本発明の変性ビニルアセタール樹脂又は、それを含む樹脂組成物からなる板状成形体の測定温度50℃、周波数1Hzの条件での貯蔵弾性率(E’)は、20~1,000MPaであることが好ましく、より好ましくは30~900MPa、さらに好ましくは40~800MPaである。貯蔵弾性率(E’)が上記範囲であると、自立性がさらに良好になる。本発明において、貯蔵弾性率(E’)は実施例に記載した方法により測定した。
本発明の板状成形体は、合わせガラス用中間膜として有用である。該合わせガラス用中間膜は、ガラス等の基材への接着性、透明性、自立性に優れる点から、特に、構造材料用合わせガラスの中間膜として好ましい。また、構造材料用合わせガラスの中間膜に限らず、自動車等の移動体、建築物、太陽電池、などの各種用途における合わせガラス用中間膜としても好適であるが、これらの用途に限定されるものではない。
本発明の板状成形体を、無機ガラス又は有機ガラスからなる2枚以上のガラスの間に挿入、積層することで合わせガラスを作製することができる。本発明の合わせガラス用中間膜と積層させるガラスは、特に制限はないが、フロートガラス、強化ガラス、網入りガラス、熱線吸収板ガラスなどの無機ガラスのほか、ポリメタクリル酸メチル、ポリカーボネートなどの従来公知の有機ガラスが使用できる。ガラスの厚さは特に制限はないが、1~10mmが好ましく、2~6mmがより好ましい。
アセタール化反応前のエチレンビニルアルコール共重合体をDMSO中に120℃下で溶解させ、室温下に冷却させた後にN,N-ジメチル-4-アミノピリジン及び無水酢酸を添加し1時間撹拌反応させ、その後イオン交換水及びアセトンで沈殿させ、洗浄、乾燥を行うことでエチレン酢酸ビニル共重合体を得た。得られたエチレン酢酸ビニル共重合体をDMSO-d6に溶解し、400MHzのプロトンNMR測定装置により、積算回数256回で測定して得られたスペクトルから、エチレン単位及び酢酸ビニル単位に由来するメチンプロトン(1.1~1.9ppmのピーク)、並びに酢酸ビニル単位に由来する末端メチルプロトン(2.0ppmのピーク)の強度比から、エチレンビニルアルコール共重合体のエチレン単位のモル割合(n)を算出した。ここで、アセタール化反応によりエチレン単位は影響を受けないことから、アセタール化反応前のエチレンビニルアルコール共重合体のエチレン単位のモル割合(n)は、アセタール化反応後に得られる変性ビニルアセタール樹脂のエチレン単位のモル割合(n)と等しいものとして扱う。
アセタール化反応前のエチレンビニルアルコール共重合体、変性ビニルアセタール樹脂、及び変性ビニルアセタール樹脂からなる樹脂組成物のメルトフローレートを、JIS K7210:2014に準拠して、190℃、2.16kg荷重の条件で測定した。
後述する方法にて得られた樹脂組成物の溶融混練物を200℃加熱下、50kgf/cm2の圧力にて5分間圧縮成形し、厚さ0.8mmのシートを得た。該シートから縦40mm×横5mmの試験片を切り出し、株式会社UBM製動的粘弾性測定装置を用いて、測定温度50℃、周波数1Hzの条件で、貯蔵弾性率(E’)を測定し、その値を高温環境下における合わせガラス用中間膜の自立性の指標とした。
後述する方法にて得られた樹脂組成物の溶融混練物を200℃加熱下、50kgf/cm2の圧力にて5分間圧縮成形し、厚さ0.8mmのシートを得た。該シートから縦60mm×横60mmの試験片を切り出し、落錘式衝撃試験機(インストロン社製CEAST9350)を用い、ASTM D3763に準拠して、測定温度23℃、荷重2kg、衝突速度9m/secの条件にて試験を行い、試験片貫通の際の、ストライカ先端が試験片に接した(試験力を感知した)瞬間から貫通する(試験力がゼロに戻る)までのSSカーブの面積から貫通エネルギーを算出した。
後述する方法にて得られた樹脂組成物を40mm径のフルフライト1軸押出機、60cm幅のコートハンガーダイを用いて、バレル温度200℃の条件で製膜して厚さ0.8mm、幅50cmのシートを製造した。このときの製膜安定性を観察し、問題なく連続製膜が可能であり外観良好なシートが得られた場合をA、シートの破断や弛みなどの問題が生じ外観良好なシートが得られなかった場合をBと評価した。
後述する方法にて得られた樹脂組成物の溶融混練物を210℃加熱下、50kgf/cm2の圧力にて5分間圧縮成形し、厚さ0.8mmのシートを得た。得られたシートを厚さ2.7mmのフロートガラス2枚に挟み、真空ラミネーター(日清紡メカトロニクス株式会社製1522N)を使用し100℃で真空ラミネーター内を1分減圧し、減圧度、温度を保持したまま30kPaで5分プレスして、仮接着体を得た。得られた仮接着体をオートクレーブに投入し140℃、1.2MPaで30分処理して、合わせガラスを得た。得られた合わせガラスを25mm×25mmの大きさに切断して試験サンプルを得た。得られた試験サンプルをWO1999/058334号公報に記載の圧縮せん断強度試験(Compressionshearstrengthtest)により評価した。合わせガラスが剥離した際の最大せん断応力を、ガラス接着性の指標とした。
上述の方法にて得られた合わせガラスを140℃まで加熱したのち、0.1℃/分の速度で23℃まで徐冷した。徐冷操作後の合わせガラスのヘイズを測定した。
(変性ビニルアセタール樹脂の合成)
特開2016-28139に記載の方法に準じて合成した、エチレン単位44モル%、ケン化度99%、MFR5.5g/10minのエチレンビニルアルコール共重合体のチップ100重量部を315重量部の1-プロパノール中に分散させ、溶液の温度を撹拌下に60℃まで昇温した後、1M塩酸を40重量部添加し、次いでn-ブチルアルデヒド16.7重量部を添加して分散させた後、60℃を保持しアセタール化反応を行った。反応が進行するにつれチップは溶解し均一な溶液となった。反応開始から36時間保持した時点で炭酸水素ナトリウム6.4重量部を添加して反応停止させた。反応液に1-プロパノールを500重量部添加して均一にした後、水2000重量部に滴下し樹脂を析出させた。その後濾過、水洗の操作を3回繰り返し、60℃にて真空乾燥を8時間実施することで変性ビニルアセタール樹脂を得た。得られた変性ビニルアセタール樹脂のエチレン単位は47モル%、アセタール化度は20モル%であった。
上記で得た変性ビニルアセタール樹脂をラボプラストミル(装置名「4M150」、株式会社東洋精機製作所製)を用いてチャンバー温度200℃、回転数100rpmにて3分間溶融混練し、チャンバー内容物を取り出し、冷却して溶融混練物を得た。得られた溶融混練物を用いて各種物性評価を行った。結果を表1に示す。
用いたエチレンビニルアルコール共重合体のエチレン単位、MFR、n-ブチルアルデヒドの添加量、反応時間を表1に示す通り変更した以外は、実施例1と同様の方法で各変性ビニルアセタール樹脂を得、実施例1と同様の方法で溶融混練し、溶融混練物を得た。得られた溶融混練物を用いて各種物性評価を行った。結果を表1に示す。
実施例2と同様の方法で各変性ビニルアセタール樹脂を得、変性ビニルアセタール樹脂100重量部に対して可塑剤としてトリエチレングリコール-ジ-2-エチルヘキサノエートを8重量部加えたこと以外は実施例1と同様の方法で溶融混練物を得た。得られた溶融混練物を用いて各種物性評価を行った。結果を表1に示す。
用いたエチレンビニルアルコール共重合体のエチレン単位、MFR、n-ブチルアルデヒドの添加量、反応時間を表2に示す通り変更した以外は、実施例1と同様の方法で各変性ビニルアセタール樹脂を得、実施例1と同様の方法で溶融混練物を得た。得られた溶融混練物を用いて各種物性評価を行った。結果を表2に示す。
ケン化度99%のビニルアルコール樹脂の7.5%水溶液1700重量部と、ブチルアルデヒド74.6重量部、2,6-ジ-t-ブチル-4-メチルフェノール0.13重量部を仕込み、全体を14℃に冷却した。これに、濃度20質量%の塩酸160.1重量部を添加して、アセタール化反応を開始した。塩酸の添加が終了してから10分後、90分かけて65℃まで昇温し、更に120分反応を行った。その後、室温まで冷却して析出した樹脂をろ過し、イオン交換水(樹脂に対して10倍量のイオン交換水で10回)で洗浄した。その後、0.3質量%水酸化ナトリウム溶液を用いて充分に中和を行い、さらに、樹脂に対して10倍量のイオン交換水で10回洗浄し、脱水したのち、乾燥させ、ビニルブチラール樹脂を得た。
比較例5と同様の方法でビニルブチラール樹脂を得、ビニルブチラール樹脂100重量部に対して可塑剤としてトリエチレングリコール-ジ-2-エチルヘキサノエートを30重量部加えたこと以外は比較例7と同様の方法で溶融混練物を得た。得られた溶融混練物を用いて各種物性評価を行った。結果を表2に示す。
特許文献3(特開2011-57737)の実施例1に記載の方法に従って、エチレン含有量15モル%、ケン化度98モル%、平均重合度1700のポリビニルアルコール100gを蒸留水900g中で撹拌したが、ポリビニルアルコールは溶解せず濃度10重量%のポリビニルアルコール水溶液を得ることはできず、アセタール化反応を行うことはできなかった。
特許文献3の実施例1に記載された、エチレン含有量15モル%、ケン化度98モル%、平均重合度1700のポリビニルアルコール及びn-ブチルアルデヒドの添加量を使用し、溶媒として1-プロパノールを使用すること等の反応条件については本願明細書の実施例1に準じて変更した方法により、変性ビニルアセタール樹脂を得た。得られた変性ビニルアセタール樹脂は73モル%のアセタール化度を有し、特許文献3に記載されているアセタール化度64.5モル%とは整合しなかった。他方、得られた変性ビニルアセタール樹脂は62モル%のアセタール単位を有し、特許文献3に記載されているアセタール化度64.5モル%に近似していた。
Claims (7)
- 樹脂を構成する全単量体単位を基準にして25~60モル%のエチレン単位、及び24~71モル%のビニルアルコール単位を含み、エチレン単位以外の構造単位のうちアセタール化されたビニルアルコール単位の占める割合として定義されるアセタール化度が5モル%以上40モル%未満である、合わせガラスの中間膜用変性ビニルアセタール樹脂。
- 80質量%以上の量で請求項1に記載の変性ビニルアセタール樹脂を含有する、合わせガラスの中間膜用樹脂組成物。
- 可塑剤の含有量が1質量%以下である、請求項2に記載の樹脂組成物。
- 請求項1に記載の変性ビニルアセタール樹脂、請求項2に記載の樹脂組成物、又は請求項3に記載の樹脂組成物から実質的になる板状成形体。
- 厚みが0.10~3mmである、請求項4に記載の板状成形体。
- 請求項4又は5に記載の板状成形体を用いてなる合わせガラス用中間膜。
- 2つのガラス板と、該2つのガラス板の間に配置された請求項6に記載の合わせガラス用中間膜とを有する、合わせガラス。
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2020
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