JP2009013060A - 合わせガラス用中間膜 - Google Patents
合わせガラス用中間膜 Download PDFInfo
- Publication number
- JP2009013060A JP2009013060A JP2008217657A JP2008217657A JP2009013060A JP 2009013060 A JP2009013060 A JP 2009013060A JP 2008217657 A JP2008217657 A JP 2008217657A JP 2008217657 A JP2008217657 A JP 2008217657A JP 2009013060 A JP2009013060 A JP 2009013060A
- Authority
- JP
- Japan
- Prior art keywords
- vinyl
- mol
- polymer
- laminated glass
- vinyl 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.)
- Granted
Links
- 239000005340 laminated glass Substances 0.000 title claims abstract description 61
- 239000011229 interlayer Substances 0.000 title claims abstract description 35
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 102
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 101
- 229920006324 polyoxymethylene Polymers 0.000 claims abstract description 97
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 33
- 239000004711 α-olefin Substances 0.000 claims abstract description 28
- 238000007127 saponification reaction Methods 0.000 claims abstract description 23
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 20
- 238000006359 acetalization reaction Methods 0.000 claims abstract description 16
- 229920000642 polymer Polymers 0.000 claims description 34
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 21
- CBECDWUDYQOTSW-UHFFFAOYSA-N 2-ethylbut-3-enal Chemical group CCC(C=C)C=O CBECDWUDYQOTSW-UHFFFAOYSA-N 0.000 claims description 13
- JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 11
- 239000005977 Ethylene Substances 0.000 claims description 11
- 125000000686 lactone group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 44
- 239000004014 plasticizer Substances 0.000 abstract description 34
- 239000010408 film Substances 0.000 description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 238000000034 method Methods 0.000 description 48
- 229920001567 vinyl ester resin Chemical group 0.000 description 32
- 239000000178 monomer Substances 0.000 description 31
- 239000000243 solution Substances 0.000 description 26
- -1 aldehyde compound Chemical class 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 17
- 239000011521 glass Substances 0.000 description 16
- 230000002087 whitening effect Effects 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 150000002596 lactones Chemical group 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000919 ceramic Substances 0.000 description 12
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 239000005357 flat glass Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 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 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- UIZVMOZAXAMASY-UHFFFAOYSA-N hex-5-en-1-ol Chemical compound OCCCCC=C UIZVMOZAXAMASY-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 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
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-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
- IBTLFDCPAJLATQ-UHFFFAOYSA-N 1-prop-2-enoxybutane Chemical group CCCCOCC=C IBTLFDCPAJLATQ-UHFFFAOYSA-N 0.000 description 1
- LWJHSQQHGRQCKO-UHFFFAOYSA-N 1-prop-2-enoxypropane Chemical group CCCOCC=C LWJHSQQHGRQCKO-UHFFFAOYSA-N 0.000 description 1
- DRYJUBPIARAFOC-UHFFFAOYSA-N 2,5-dimethyl-4-oxohexa-2,5-dienoic acid Chemical class CC(=C)C(=O)C=C(C)C(O)=O DRYJUBPIARAFOC-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 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
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- SSKNCQWPZQCABD-UHFFFAOYSA-N 2-[2-[2-(2-heptanoyloxyethoxy)ethoxy]ethoxy]ethyl heptanoate Chemical compound CCCCCCC(=O)OCCOCCOCCOCCOC(=O)CCCCCC SSKNCQWPZQCABD-UHFFFAOYSA-N 0.000 description 1
- JWCDUUFOAZFFMX-UHFFFAOYSA-N 2-ethenoxy-n,n-dimethylethanamine Chemical group CN(C)CCOC=C JWCDUUFOAZFFMX-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical group OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- OPVZITRSTBLYCG-UHFFFAOYSA-M 2-ethenoxyethyl(trimethyl)azanium;chloride Chemical group [Cl-].C[N+](C)(C)CCOC=C OPVZITRSTBLYCG-UHFFFAOYSA-M 0.000 description 1
- XEEYSDHEOQHCDA-UHFFFAOYSA-N 2-methylprop-2-ene-1-sulfonic acid Chemical compound CC(=C)CS(O)(=O)=O XEEYSDHEOQHCDA-UHFFFAOYSA-N 0.000 description 1
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 description 1
- OJXVWULQHYTXRF-UHFFFAOYSA-N 3-ethenoxypropan-1-ol Chemical group OCCCOC=C OJXVWULQHYTXRF-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical group OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 1
- QGFSQVPRCWJZQK-UHFFFAOYSA-N 9-Decen-1-ol Chemical compound OCCCCCCCCC=C QGFSQVPRCWJZQK-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
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- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- TZYULTYGSBAILI-UHFFFAOYSA-M trimethyl(prop-2-enyl)azanium;chloride Chemical group [Cl-].C[N+](C)(C)CC=C TZYULTYGSBAILI-UHFFFAOYSA-M 0.000 description 1
- ZQYKGADTDCTWSZ-UHFFFAOYSA-N trimethyl-[(prop-2-enoylamino)methyl]azanium;chloride Chemical group [Cl-].C[N+](C)(C)CNC(=O)C=C ZQYKGADTDCTWSZ-UHFFFAOYSA-N 0.000 description 1
- CCVMLEHYQVSFOM-UHFFFAOYSA-N trimethyl-[2-(prop-2-enoylamino)ethyl]azanium;chloride Chemical group [Cl-].C[N+](C)(C)CCNC(=O)C=C CCVMLEHYQVSFOM-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
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- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10761—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing vinyl acetal
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/62218—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products obtaining ceramic films, e.g. by using temporary supports
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
- C04B35/634—Polymers
- C04B35/63404—Polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C04B35/6342—Polyvinylacetals, e.g. polyvinylbutyral [PVB]
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/48—Isomerisation; Cyclisation
-
- 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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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
- C04B2235/02—Composition of constituents of the starting material or of secondary phases of the final product
- C04B2235/30—Constituents and secondary phases not being of a fibrous nature
- C04B2235/32—Metal oxides, mixed metal oxides, or oxide-forming salts thereof, e.g. carbonates, nitrates, (oxy)hydroxides, chlorides
- C04B2235/3231—Refractory metal oxides, their mixed metal oxides, or oxide-forming salts thereof
- C04B2235/3232—Titanium oxides or titanates, e.g. rutile or anatase
- C04B2235/3234—Titanates, not containing zirconia
- C04B2235/3236—Alkaline earth titanates
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
- C04B2235/02—Composition of constituents of the starting material or of secondary phases of the final product
- C04B2235/50—Constituents or additives of the starting mixture chosen for their shape or used because of their shape or their physical appearance
- C04B2235/54—Particle size related information
- C04B2235/5418—Particle size related information expressed by the size of the particles or aggregates thereof
- C04B2235/5445—Particle size related information expressed by the size of the particles or aggregates thereof submicron sized, i.e. from 0,1 to 1 micron
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
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- C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
- C04B2235/60—Aspects relating to the preparation, properties or mechanical treatment of green bodies or pre-forms
- C04B2235/61—Mechanical properties, e.g. fracture toughness, hardness, Young's modulus or strength
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
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- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/01—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics
- C04B35/46—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics based on titanium oxides or titanates
- C04B35/462—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics based on titanium oxides or titanates based on titanates
- C04B35/465—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics based on titanium oxides or titanates based on titanates based on alkaline earth metal titanates
- C04B35/468—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics based on titanium oxides or titanates based on titanates based on alkaline earth metal titanates based on barium titanates
- C04B35/4682—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics based on titanium oxides or titanates based on titanates based on alkaline earth metal titanates based on barium titanates based on BaTiO3 perovskite phase
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Organic Chemistry (AREA)
- Ceramic Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Structural Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Joining Of Glass To Other Materials (AREA)
Abstract
【解決手段】 α−オレフィン単位を1〜15モル%含有し、1,2−グリコール結合の含有量が1〜3モル%、重合度が500〜2000、けん化度が80.0〜99.99モル%のビニルアルコール系重合体をアセタール化して得られる、アセタール化度が45〜80モル%のビニルアセタール系重合体からなる合わせガラス用中間膜により上記課題が解決される。
【選択図】 なし
Description
特に、ビニルブチラール系重合体は、自動車や建築物の窓ガラスの中間膜として用いられているだけでなく、セラミック成形用バインダー、感光性材料、インキ用分散剤などの種々の工業用分野において広く用いられている。
特に近年、携帯電話、ノート型パソコンなどの精密電気機器などについて小型化・軽量化することが望まれるようになっており、これらに用いられる電気・電子部品についても小型化・高性能化が求められている。
すなわち、本発明は、α−オレフィン単位を1〜15モル%含有し、1,2−グリコール結合の含有量が1〜3モル%、重合度が500〜2000、けん化度が80.0〜99.99モル%のビニルアルコール系重合体をアセタール化して得られる、アセタール化度が45〜80モル%のビニルアセタール系重合体を主成分とする安全ガラス用中間膜である。
本発明の合わせガラス用中間膜はこのようなビニルアセタール系重合体を主成分とするものであり、合わせガラスとの接着性接着性に優れており、また得られる合わせガラスは端部の耐白化性に優れている。
本発明において、ビニルアセタール系重合体は、α−オレフィン単位を1〜15モル%含有し、1,2−グリコール含有量が1〜3モル%、重合度が500〜2000、けん化度が80.0〜99.99モル%のビニルアルコール系重合体をアセタール化することにより製造される。
P=([η]×1000/8.29)(1/0.62)
(1)PVAの前駆体であるα−オレフィン単位を含有するポリビニルエステルをn−ヘキサン/アセトンで再沈精製を3回以上十分に行った後、80℃の温度で減圧下に3日間乾燥を行うことにより、分析用の試料を作成する。例えば、PVA中に含まれるα−オレフィン単位の種類がエチレンの場合には、分析用の試料をDMSO−d6に溶解して80℃でプロトンNMRを測定し、ビニルエステルの主鎖メチンに由来するピーク(4.7〜5.2ppm)とエチレンおよびビニルエステルの主鎖メチレンに由来するピーク(0.8〜1.6ppm)からエチレンの含有量を算出する。
−0.012×Fn+1.24≦含有量(モル%)≦−0.022×Fn
+2.23 ・・・(1)
(上記式中、含有量(モル%)は1,2−グリコール結合の含有量を表し、Fnはα−オレフィン単位の含有量(モル%)を表す。)
1,2−グリコール結合含有量(モル%)=B×(100−Et)/100A
(上記式中、Etはエチレン変性量(モル%)を表す。)
−1.95×10−5×P+0.045≦含有量(モル%)≦−1.38×
10−4×P+0.91 ・・・(2)
(上記式中、含有量(モル%)はカルボン酸及びラクトン環の含有量を表し、Pはビニルアルコール系重合体の粘度平均重合度を表す。)
分析用の試料をDMSO−d6に溶解し、プロトンNMRを用いて60℃で測定する。アクリル酸、アクリル酸エステル類、アクリルアミド、アクリルアミド誘導体などの単量体は、主鎖メチンに由来するピーク(2.0ppm)から、またメタクリル酸、メタクリル酸エステル類、メタクリルアミド、メタクリルアミド誘導体などの単量体は、主鎖に直結するメチル基に由来するピーク(0.6〜1.1ppm)から、常法により含有量を算出する。フマール酸、マレイン酸、イタコン酸、無水マレイン酸、無水イタコン酸などに由来するカルボキシル基を有する単量体は、分析用の試料をDMSO−d6に溶解し、トリフルオロ酢酸を数滴加えた後、プロトンNMRを用いて60℃で測定する。ラクトン環のメチンピーク(4.6〜5.2ppm)から、常法により含有量を算出する。
硫黄原子に結合するメチレンに由来するピーク(2.8ppm)から、含有量を算出する。
(iii)の場合
分析用の試料をメタノール−d4/D2O=2/8に溶解し、プロトンNMRを用いて80℃で測定する。末端のカルボン酸もしくはそのアルカリ金属塩のメチレン(下記の構造式1および構造式2)に由来するピーク(2.2ppm;積分値A、2.3ppm;積分値B)、末端のラクトン環のメチレン(下記の構造式3)に由来するピーク(2.6ppm;積分値C)、ビニルアルコール単位のメチンに由来するピーク(3.5〜4.15ppm;積分値D)から、下記式を用いて含有量を算出する。
=50×(A+B+C)×(100−Fn)/(100×D)
(上記式中、Fnはα−オレフィンの変性量(モル%)を表す。)
(Na)HOOCCH2CH2CH2〜
NaOOCCH2CH2CH(OH)〜
また、必要に応じて、カルボン酸を含有するアルデヒド化合物を併用してもよい。
PVAの分析は、特に断らない限りJIS−K6726に記載の方法にしたがって行った。
PVAに含まれるα−オレフィン単量体の量、カルボン酸およびラクトン環の含有量、並びに1,2−グリコール結合の含有量は、前述した方法にしたがって、500MHzのプロトンNMR測定装置(JEOL GX−500)を用いて求めた。
ビニルアセタール系重合体のアセタール化度は、DMSO−d6に溶解したサンプルを500MHzのプロトンNMR測定装置(JEOL GX−500)を用いて求めた。
(PVAの合成)
撹拌機、窒素導入口、エチレン導入口、開始剤の添加口およびディレー溶液の添加口を備えた250Lの加圧反応槽に酢酸ビニル124.4kg、メタノール25.5kgを仕込み、60℃に昇温した後30分間窒素ガスによるバブリングを行い、系中を窒素置換した。次いで、反応槽の圧力が0.48MPaとなるようにエチレンを導入した。開始剤として2,2’−アゾビス(4−メトキシ−2,4−ジメチルバレロニトリル)をメタノールに溶解して濃度2.8g/Lの溶液を調製し、これに窒素ガスによるバブリングを行って窒素置換した。上記反応槽の内温を60℃に調整した後、上記の開始剤溶液90mlを注入し、重合を開始した。重合中は重合温度を60℃に維持し、上記の開始剤溶液を280ml/hrで連続的に添加して重合を実施した。4時間経過後、重合率が40%となったところで、反応槽を冷却して重合を停止した。なお、重合時に反応槽の圧力が除々に低下するように操作し、重合が終了した時点で反応槽の圧力は0.44MPaまで低下した。重合を停止した後、反応槽を開放して脱エチレンした後、窒素ガスをバブリングして脱エチレンを完全に行った。次いで、重合後の反応液にメタノール蒸気を導入することで未反応の酢酸ビニル単量体を追い出し、ビニルエステル系重合体を40%含有するメタノール溶液を得た。
ビニルエステル系重合体を40%含有するメタノール溶液を用い、これに適当量のメタノール、水酸化ナトリウム10重量%を含有するメタノール溶液をこの順番で加え、40℃でけん化反応を開始した。なお、けん化反応開始時のビニルエステル系重合体の固形分濃度は30重量%であった。水酸化ナトリウムを含有するメタノール溶液の添加は攪拌下に行われ、水酸化ナトリウムの添加量はビニルエステル系重合体の酢酸ビニル単位に対するモル比で0.02であった。水酸化ナトリウムを含有するメタノール溶液の添加を開始して約2分後に得られたゲル化物を粉砕器にて粉砕し、40℃で1時間放置してけん化を進行させた後、酢酸メチルを加えて残存するアルカリを中和した。フェノールフタレイン指示薬を用いて中和が終了したことを確認した後、白色のPVA固体を濾別した。得られたPVA固体に5倍量のメタノールを加え、室温で3時間放置するという操作でPVA固体を洗浄した。上記の洗浄操作を3回繰り返した後、遠心法により脱液したPVAを乾燥機に入れ、70℃で1日間放置して乾燥を行った。このようにして(PVA−1a)を得た。
反応条件を表1〜表6に示す内容に変更した以外はPVA−1aと同様にして、各種のPVA(PVA−2a〜PVA−30a及びPVA−1b〜PVA−24b)を合成した。各PVAについてその分析値を表7〜表12に示す。
(ビニルアセタール系重合体の合成)
480gのPVA(PVA−1a)を5520mlの水中に投入し、溶液の温度を攪拌下に90℃まで昇温して溶解させた後、30℃まで冷却し、ブチルアルデヒド271gを添加して分散させた後14℃まで冷却し、20%濃度の塩酸溶液72gを添加して反応を開始し、溶液の温度を14℃に保ちつつ20分間で滴下した。塩酸溶液の滴下後、溶液の温度が14℃の状態で40分間反応を行った後、20%濃度の塩酸溶液330gを30分間で滴下し、その滴下終了後、約0.6℃/分の昇温速度で65℃まで温度を上げ、溶液の温度が65℃の状態を60分間維持した。その後、反応溶液を室温まで冷却し、析出した粒状物を濾別して水で十分に洗浄した。洗浄後の粒状物を中和させるために、該粒状物を0.3%水酸化カリウム溶液に入れ、該溶液を70℃で再び穏やかに加温した。さらに、水で洗浄することによって過剰のアルカリを除去した後、粒状物を乾燥した。このようにしてビニルアセタール系重合体(VAP−1a)を得た。
反応条件を表13〜表18に示す内容に変更した以外はVAP−1aと同様にして、各種のビニルアセタール系重合体(VAP−2a〜VAP−37a及びVAP−1b〜VAP−30b)を合成した。各ビニルアセタール系重合体についてその分析値を表13〜表18に示す。
(平衡含水率)
フィルムを20℃、90%RHの雰囲気に2週間放置し、放置前後のフィルムの重量変化から平衡含水率を測定した。なお、平衡含水率は次式より算出した。
平衡含水率(%)=(放置後のフィルムの重量−放置前のフィルムの重量)/放置前のフィルムの重量×100
(吸水率)
20℃の蒸留水にフィルムを24時間浸漬し、フィルムの表面に付着した水をカーゼで完全に拭き取った後、浸漬前後のフィルムの重量変化から吸水率を測定した。なお、吸水率は次式より算出した。
吸水率(%)=(浸漬後のフィルムの重量−浸漬前のフィルムの重量)/浸漬前のフィルムの重量×100
(可塑剤との相溶性)
ビニルアセタール系重合体(VAP−1a)100部に対して、トリエチレングリコール−ジ2−エチルヘキサノエート40部を加えて可塑化し、70℃にて5分間ロール練りを行い、さらに170℃、5MPaの条件でプレスすることにより、厚さ0.6mmの可塑化フィルムを作成した。可塑化フィルムの重量(初期の重量)を予め測定し、そして重量を測定した後の可塑化フィルムを30℃、80%RHの雰囲気に2週間放置し、表面にブリードした可塑剤をガーゼで完全に拭き取った後、五酸化二リンの存在下にデシケータ中で2週間放置し、重量を測定(試験後の重量)した。試験前後の可塑化フィルムの重量変化率を次式より求め、以下の基準にしたがって可塑剤との相溶性を評価した。
重量変化率(%)=(初期の重量−試験後の重量)/初期の重量×100
判断基準:
A:重量変化率が1%未満
B:重量変化率が1%以上3%未満
C:重量変化率が3%以上
表13に示すビニルアセタール系重合体(VAP−2a〜VAP−14a)について、実施例1と同様にして、平衡含水率および吸水率を測定し、さらにビニルアセタール系重合体と可塑剤との相溶性を評価した。測定結果および評価結果を表19に示す。
表14に示すビニルアセタール系重合体(VAP−1b〜VAP−9b)について、実施例1と同様にして、平衡含水率および吸水率を測定し、さらにビニルアセタール系重合体と可塑剤との相溶性を評価した。測定結果および評価結果を表20に示す。
一方、表20に示す結果より、本発明で規定する範囲外の物性を有するであるビニルアセタール系重合体は、特に可塑剤との相溶性が著しく劣っていることが分かる。
実施例1の可塑剤との相溶性の評価に用いた可塑化フィルムの製造において、ビニルアセタール系重合体(VAP−1a)に対して酢酸マグネシウム50ppmを添加した以外は同様にして、厚み0.6mmの可塑化フィルムを得た。得られた可塑化フィルムを2枚のガラス板(厚さ2.5mm、幅300mm、長さ300mm)の間に挟んでゴムバックに入れ、15mmHg減圧下で15分間脱気し、100℃の条件で20分間真空プレスして仮接着を行った後、ゴムバックから取り出し、オートクレーブを用いて130℃、1.5MPaの条件で15分間本接着を実施した。このようにして得られた合わせガラスについて、合わせガラス周縁部の白化の状態を以下の方法により評価し、さらに可塑化フィルムのガラス板に対する接着性をパンメル値で評価した。評価結果を表21に示す。
(合わせガラス周縁部の白化の状態)
合わせガラスを80℃、95%RHの雰囲気に1ヶ月間放置した後、端部からの白化距離を測定した。なお、白化距離は、合わせガラスの端部から連続して白化している部分の距離を白化距離として測定し、以下の基準にしたがって白化の状態を評価した。
A:端部からの白化距離が1mm未満
B:端部からの白化距離が1mm以上5mm未満
C:端部からの白化距離が5mm以上
(パンメル値)
合わせガラスを−18℃の温度で1時間以上放置した後、頭部の重さが1ポンドのハンマーで打って、ガラスの粒子径が6mm以下になるまで粉砕した。割れたガラス片を振り落とし、可塑化フィルムの露出度(%)を、以下の基準にしたがってパンメル値で評価した。パンメル値が大きいほど可塑化フィルムのガラス板に対する接着性が良好であることを示す。
可塑化フィルムの露出度(%) パンメル値
100 0
90 1
85 2
60 3
40 4
20 5
10 6
5 7
2以下 8
表13に示すビニルアセタール系重合体(VAP−2a〜VAP−14a)を用いた場合の合わせガラス用中間膜について、実施例15と同様にして、合わせガラス周縁部の白化の状態および可塑化フィルムのガラス板に対する接着性を評価した。評価結果を表21に示す。
表14に示すビニルアセタール系重合体(VAP−1b〜VAP−9b)を用いた場合の合わせガラス用中間膜について、実施例15と同様にして、合わせガラス周縁部の白化の状態および可塑化フィルムのガラス板に対する接着性を評価した。評価結果を表22に示す。
一方、表22に示す結果より、本発明で期待する範囲外の物性を有するビニルアセタール系重合体から得られた合わせガラス用中間膜は、特に合わせガラス端部の耐白化性において著しく劣っていることが分かる。
Claims (7)
- α−オレフィン単位を1〜15モル%含有し、1,2−グリコール結合の含有量が1〜3モル%、重合度が500〜2000、けん化度が80.0〜99.99モル%のビニルアルコール系重合体をアセタール化して得られる、アセタール化度が45〜80モル%のビニルアセタール系重合体を主成分とする合わせガラス用中間膜。
- α−オレフィン単位がエチレンに基づく単位である請求項1記載のビニルアセタール系重合体を主成分とする合わせガラス用中間膜。
- ビニルアセタール系重合体がビニルブチラール系重合体である請求項1記載のビニルアセタール系重合体を主成分とする合わせガラス用中間膜。
- ビニルアルコール系重合体が下記式(1)を満足するものである請求項1記載のビニルアセタール系重合体を主成分とする合わせガラス用中間膜。
−0.012×Fn+1.24≦含有量(モル%)≦−0.022×Fn
+2.23 ・・・(1)
(上記式中、含有量(モル%)は1,2−グリコール結合の含有量を表し、Fnはα−オレフィン単位の含有量(モル%)を表す。) - ビニルアルコール系重合体がカルボン酸およびラクトン環を0.02〜5モル%含有することを特徴とする請求項1記載のビニルアセタール系重合体を主成分とする合わせガラス用中間膜。
- ビニルアルコール系重合体が下記式(2)を満足するものである請求項5記載のビニルアセタール系重合体を主成分とする合わせガラス用中間膜。
−1.95×10−5×P+0.045≦含有量(モル%)≦−1.38×
10−4×P+0.91 ・・・(2)
(上記式中、含有量(モル%)はカルボン酸及びラクトン環の含有量を表し、Pはビニルアルコール系重合体の粘度平均重合度を表す。) - 請求項1〜6のいずれかに記載の合わせガラス用中間膜を用いて作製した合わせガラス。
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- 2003-07-17 DE DE60302726T patent/DE60302726T2/de not_active Expired - Lifetime
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Also Published As
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EP1384731A1 (en) | 2004-01-28 |
DE60302726T2 (de) | 2006-08-03 |
JP5199791B2 (ja) | 2013-05-15 |
CN1495205A (zh) | 2004-05-12 |
US20040024137A1 (en) | 2004-02-05 |
EP1384731B1 (en) | 2005-12-14 |
CN1249108C (zh) | 2006-04-05 |
DE60302726D1 (de) | 2006-01-19 |
US6992130B2 (en) | 2006-01-31 |
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