JP6709221B2 - アクリル系ポリビニルアセタールフィルム及び組成物 - Google Patents
アクリル系ポリビニルアセタールフィルム及び組成物 Download PDFInfo
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- JP6709221B2 JP6709221B2 JP2017530059A JP2017530059A JP6709221B2 JP 6709221 B2 JP6709221 B2 JP 6709221B2 JP 2017530059 A JP2017530059 A JP 2017530059A JP 2017530059 A JP2017530059 A JP 2017530059A JP 6709221 B2 JP6709221 B2 JP 6709221B2
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- JP
- Japan
- Prior art keywords
- film
- meth
- acrylate
- composition
- polyvinyl acetal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920002554 vinyl polymer Polymers 0.000 title claims description 64
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title claims description 57
- 239000000203 mixture Substances 0.000 title description 137
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title description 10
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 title 1
- 239000000178 monomer Substances 0.000 claims description 118
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 45
- 229920000058 polyacrylate Polymers 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 229920006324 polyoxymethylene Polymers 0.000 claims description 34
- 239000011354 acetal resin Substances 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 18
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 10
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 230000009477 glass transition Effects 0.000 claims description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 31
- -1 acrylate ester Chemical class 0.000 description 28
- 238000000034 method Methods 0.000 description 28
- 150000001241 acetals Chemical class 0.000 description 27
- 230000005855 radiation Effects 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 239000000654 additive Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 239000000499 gel Substances 0.000 description 12
- 239000004971 Cross linker Substances 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 238000004132 cross linking Methods 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000004372 Polyvinyl alcohol Substances 0.000 description 8
- 229910021485 fumed silica Inorganic materials 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 229920002451 polyvinyl alcohol Polymers 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000006188 syrup Substances 0.000 description 7
- 235000020357 syrup Nutrition 0.000 description 7
- 238000010998 test method Methods 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 6
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 5
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 5
- 150000001336 alkenes Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011256 inorganic filler Substances 0.000 description 5
- 229910003475 inorganic filler Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 229930182556 Polyacetal Natural products 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000004404 heteroalkyl group Chemical group 0.000 description 3
- 125000005394 methallyl group Chemical group 0.000 description 3
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920002689 polyvinyl acetate Polymers 0.000 description 3
- 239000011118 polyvinyl acetate Substances 0.000 description 3
- 239000011164 primary particle Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 2
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 description 2
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 238000006359 acetalization reaction Methods 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 229910052717 sulfur Chemical group 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- 239000001618 (3R)-3-methylpentan-1-ol Substances 0.000 description 1
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- 239000005968 1-Decanol Substances 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- YMZIFDLWYUSZCC-UHFFFAOYSA-N 2,6-dibromo-4-nitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1Br YMZIFDLWYUSZCC-UHFFFAOYSA-N 0.000 description 1
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 description 1
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Description
一実施形態において、フィルムが記載される。本フィルムは(メタ)アクリルポリマーとポリビニルアセタール樹脂とを含む。ポリビニルアセタール樹脂は、式
[式中、R1は水素又はC1〜C7アルキル基である。]を有する重合単位を含む。一実施形態において、フィルムは30℃〜60℃の範囲のガラス転移温度(即ちTg)を有する。別の実施形態において、フィルムは少なくとも20%のゲル含有量を有する。別の実施形態において、フィルムは少なくとも175%の破断伸度を有する。本フィルムは、典型的には、フィルムを製造した方法の結果として光開始剤を含む。本フィルムはモノリシックフィルムであっても、又は多層フィルムの(例えば外側)層であってもよい。
本明細書には、(メタ)アクリルポリマーとポリビニルアセタール樹脂とを含むフィルム及び組成物、並びに製造方法が開示される。本組成物は、好ましくは、ポリビニルアセタール樹脂をフリーラジカル重合性溶媒モノマーに溶解することによって調製される。溶媒モノマーは、好ましくは(例えば紫外)放射線の照射によって重合する。
H2C=CR1C(O)OR8
(式中、R1はH又はメチルであり、R8は、1〜22個の炭素を有するアルキル、又は2〜20個の炭素及び酸素若しくは硫黄から選択される1〜6個のヘテロ原子を有するヘテロアルキルである)を有していてもよい。アルキル基又はヘテロアルキル基は、直鎖状、分枝状、環状、又はこれらの組み合わせであり得る。
化学式1において、nは、アセタール化に用いられる異なる種類のアルデヒドの数であり;R1,R2,...,Rnは、独立して、アセタール化反応に用いられるアルデヒドの(例えばC1〜C7)アルキル残基、又は水素原子であり;k1,k2,...,knは、独立して、R1,R2,...,Rnを含有する各アセタール単位の割合(モル比)であり;lはビニルアルコール単位の割合(モル比)であり;及びmは酢酸ビニル単位の割合(モル比)である。k1+k2+...+kn+l+mの合計=1。更に、k1,k2,...,knのうちの少なくとも1つはゼロでなくてもよい。ポリビニルアセタール樹脂の調製に単一の種類のアルデヒドが利用される場合、かかる単一のアルデヒドはk1によって表されてもよい。k1+l+mの繰り返し単位の数は、所望の分子量をもたらすのに十分である。この実施形態において、k2及びknは0であってもよい。ポリアセタール樹脂は、典型的にはランダム共重合体である。しかしながら、ブロック共重合体及びテーパードブロック共重合体もランダム共重合体と同様の有益性をもたらし得る。
(式中、R1はH又はCH3であり、
Lは任意の結合基であり、かつ、
R2はオレフィン基であって、任意に置換されているオレフィン基である。)。
(式中、このトリアジン架橋剤のR1、R2、R3及びR4は独立して水素又はアルコキシ基であり、R1、R2、R3及びR4のうちの1〜3個は水素である)を有してもよい。アルコキシ基は、典型的には、12個以下の炭素原子を有する。有利な実施形態において、アルコキシ基は独立してメトキシ又はエトキシである。1つの代表的な種は、2,4,−ビス(トリクロロメチル)−6−(3,4−ビス(メトキシ)フェニル)−トリアジンである。このようなトリアジン架橋化合物は、米国特許第4,330,590号に更に記載される。
実施形態1は、(メタ)アクリルポリマーと、以下の式
[式中、R1は水素又はC1〜C7アルキル基である。]を有する重合単位を含むポリビニルアセタール樹脂と、を含み、
30℃〜60℃の範囲のTgを有する、フィルムである。
[式中、R1は水素又はC1〜C7アルキル基である。]を有する重合単位を含むポリビニルアセタール樹脂と、を含み、
少なくとも20%のゲル含有量を有する、フィルムである。
(メタ)アクリルポリマーと、以下の式
[式中、R1は水素又はC1〜C7アルキル基である。]を有する重合単位を含むポリビニルアセタール樹脂と、を含み、
少なくとも175%の破断伸度、少なくとも30%の引張永久ひずみ、又はこれらの組み合わせを有する、フィルムである。
a)組成物を提供する工程であって、組成物が、
i)以下の式
[式中、R1は水素又はC1〜C7アルキル基である。]を有する重合単位を含むポリビニルアセタール樹脂と、
ii)アルキル(メタ)アクリレートモノマーを含むフリーラジカル重合性溶媒モノマーとを含む、工程、
b)組成物を基材に塗布する工程、及び
c)溶媒モノマーを重合させ、任意に組成物を架橋結合して、それにより組成物を形成する工程を含み、組成物が、30℃〜60℃の範囲のTg、少なくとも20%のゲル含有量、及び少なくとも175%の伸び、又はこれらの組み合わせによって特徴付けられる、フィルムの作製方法である。
[式中、R1は水素又はC1〜C7アルキル基である。]を有する重合単位を含むポリビニルアセタール樹脂と、を含み、
30℃〜60℃の範囲のTg、少なくとも20%のゲル含有量、及び少なくとも175%の伸び、又はこれらの組み合わせによって特徴付けられる、組成物である。
引張強さ及び伸び試験
INSTRON MODEL 4500 UNIVERSAL TESTING SYSTEMを1kNロードセルと共に利用して、引張及び伸び試験をASTM D882−10(特に指定のない限り)に従い実施した。試験は250mm(9.84インチ)の総距離について300mm/分(11.81インチ/分)の速度で実施した。試料は調製から24時間以上後に試験した。0.5インチ(約1.3cm)幅ストリップのフィルムをカットし、マイクロメータを使用して各試料の厚さを決定した。典型的な試料長さは5〜7cm(2〜3インチ)であった。試験結果は、3〜5つの試料レプリケートの平均として報告した。引張強さ(名目)及びパーセント破断伸度を、ASTM D882−10の11.3及び11.5により記載されるとおり決定した。
約5mgのフィルム試料の各々を個々の標準アルミニウムDSCパン(Thermal Analysis T080715)に置き、示差走査熱量計(TA DSC Q200、TA Instruments)のオートサンプラーに置いた。各試料分析について、パンを個々に熱量計の密閉セル内の示差ポストの一方に、反対側のポストの空の基準パンと共に置いた。温度を5℃/分の速度で150℃に上昇させ、−50℃に冷却し、もう一度+150℃に再加熱した。2回目の加熱サイクルを用いてTg(ASTM D3418−12でTmgとして記載されている中点値温度を指す)を決定した。
アルミニウムパンを秤量し、その重量(W1)を記録した。パンにメッシュバスケットを置き、次に秤量し(バスケット及びパン)、その重量(W2)を記録した。1インチ(2.54センチメートル)直径の接着剤試料をバスケットに入れ、試料(パン、バスケット、及び接着剤試料)を再び秤量し(W3)、記録した。次に試料(バスケット及び接着剤試料)をガラスジャーに置き、テトラヒドロフランで覆い、3日間放置した。次に、試料(バスケット及び接着剤試料)をテトラヒドロフランから取り出し、パンに戻した。試料(パン、バスケット、及び接着剤試料)を120℃のオーブンに2時間入れた。オーブンから試料を取り出し、放冷した。続いて、試料を秤量し、その重量(W4)を記録した。%ゲル含有量=100(W4−W2)/(W3−W2)。
以下のとおりASTM D412−6ae2:「加硫ゴム及び熱可塑性エラストマーの標準試験方法−張力(Standard Test Methods for Vulcanized Rubber and ThermoplasticElastomers-Tension)」にしたがい引張永久ひずみ試験方法を用いて追従性を評価した。幅2.54cm(1インチ)及び長さ10.2cm(4インチ)の試験片を用いた。フィルム試験片上に初期ジョー分離距離(50.8mm)をマークし、次に試験片を304.8mm/分(12インチ/分)の速度でその元の長さの50%超(76.2mm)まで引き伸ばし、30秒間保持した。次に試験片をジョーグリップから取り外し、24時間後(又は他の指定した時間後)に元のマーク間の長さを再計測した。引張永久ひずみ率パーセントによって計測したときの追従性を、
%引張永久ひずみ=[(L24−L0)/(L1−L0)]×100
[式中、L24は24時間後(又は他の指定した時間後)の長さ計測値であり、L0は初期ジョー分離距離であり、及びL1は伸びた長さの50%である。]として計算した。100%の引張永久ひずみ値が弾性回復ゼロに相当する。かかる値を有するフィルムは、収縮することなく引き伸ばされた状態に留まり得る。
クォートジャーに表2に示すとおりの2−OA、IBOA、及びAA又はNNDMAを入れることにより、比較例A及びBを作製した。モノマー混合物を−20水銀柱インチ(−6.8kPa)で5分間脱気し、窒素で5〜10分間パージし、次にコーティング可能なプレポリマーシロップが調製されるまで低強度UV A光線(10mW/cm2未満、出力が主に320〜390nmであって、ピーク放射がUV Aスペクトル域内にある約350nmであるためUV Aと称される)を照射した。
モノマー、PVBポリマー、及び他の成分の混合物をクォートジャーに加えた。このジャー及び内容物をMAX 20 WHITE SPEEDMIXER(FleckTek,Inc.,Landrum,SCから入手可能)に置き、3500RPMで1分間混合した。この混合物を−20インチの水銀柱(−6.8kPa)で5分間脱気した。
以下の表3の成分をUV重合させることにより、アクリル系ポリマーを形成した。
TA InstrumentsのDMAQ800を引張モードで使用した動的機械分析(DMA)によって実施例7を分析し、各試料について温度の関数としての物理的特性を特徴付けた。6.2mm幅及び0.05〜0.07mm厚の矩形試料を17〜19mm長さで装置のフィルムテンションクランプに固定した。炉を閉め、温度を−50℃に平衡化させて5分間保持した。次に温度を3℃/分で−50℃から50℃に上昇させると同時に、試料を10ヘルツの周波数及び0.1%の一定歪みで振動させた。温度上昇中にこの材料の多くの物理的パラメータを記録したが、25℃における引張貯蔵弾性率(E’)は1770MPa(即ち1.77×1010ダイン/cm2)と記録された。
2層を有する多層フィルム、実施例14を調製した。第1の層は実施例12と同じ組成であり、3milの厚さを有した。第2の層は、以下の組成を有する厚さ3.5milの(熱結合性)組成物であった。
破断点伸び:210%
ヤング率:81,500psi(555MPa)
硬化した(熱結合性)第2のフィルム層のTg=−32.6℃
硬化した第1のフィルム層のTg=41.9℃
Claims (10)
- (メタ)アクリルポリマーと、以下の式
[式中、R1は水素又はC1〜C7アルキル基である。]
を有する重合単位を含むポリビニルアセタール樹脂と、を含み、
0℃未満のガラス転移温度(Tg)を有する単官能性アルキル(メタ)アクリレートモノマーの重合単位を10重量%以上含み、
示差走査熱量測定(DSC)によって計測したとき、30℃〜60℃の範囲の単一のTgを有する、フィルム。 - 8個の炭素原子を含むアルキル基を有するアルキル(メタ)アクリレートモノマーの重合単位を含む、請求項1に記載のフィルム。
- 40℃超のTgを有する単官能性アルキル(メタ)アクリレートモノマーの重合単位を35重量%以下更に含む、請求項1又は2に記載のフィルム。
- 酸官能性、ヒドロキシル官能性モノマー、窒素含有モノマー、及びこれらの組み合わせから選択される極性モノマーの重合単位を、10重量%以上65重量%以下更に含む、請求項1〜3のいずれか一項に記載のフィルム。
- ポリビニルアセタール樹脂を5〜30重量%含む、請求項1〜4のいずれか一項に記載のフィルム。
- 前記フィルムが多官能性架橋剤の重合単位を更に含み、前記架橋剤が、(メタ)アクリレート、アルケニル、及びヒドロキシル反応性基から選択される官能基を有する、請求項1〜5のいずれか一項に記載のフィルム。
- 前記フィルムが光開始剤を含む、請求項1〜6のいずれか一項に記載のフィルム。
- モノリシックフィルム又は多層フィルムのフィルム層である、請求項1〜7のいずれか一項に記載のフィルム。
- 前記多層フィルムが第2のフィルム層を更に含み、前記第2のフィルム層が(メタ)アクリルポリマーとポリビニルアセタール樹脂とを含み、前記第2のフィルム層が30℃未満のTgを有する、請求項8に記載のフィルム。
- 少なくとも20%のゲル含有量を有する、請求項1に記載のフィルム。
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US11629250B2 (en) | 2023-04-18 |
US10167386B2 (en) | 2019-01-01 |
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US20190092936A1 (en) | 2019-03-28 |
CN107108922A (zh) | 2017-08-29 |
KR20170092652A (ko) | 2017-08-11 |
US10870750B2 (en) | 2020-12-22 |
US20230220188A1 (en) | 2023-07-13 |
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