JP5680029B2 - 可塑剤含有ポリビニル(n)アセタール及び可塑剤含有ポリビニル(イソ)アセタールの層を備える高強度シート積層体 - Google Patents
可塑剤含有ポリビニル(n)アセタール及び可塑剤含有ポリビニル(イソ)アセタールの層を備える高強度シート積層体 Download PDFInfo
- Publication number
- JP5680029B2 JP5680029B2 JP2012163016A JP2012163016A JP5680029B2 JP 5680029 B2 JP5680029 B2 JP 5680029B2 JP 2012163016 A JP2012163016 A JP 2012163016A JP 2012163016 A JP2012163016 A JP 2012163016A JP 5680029 B2 JP5680029 B2 JP 5680029B2
- Authority
- JP
- Japan
- Prior art keywords
- polyvinyl
- acetal
- iso
- plasticizer
- mass
- 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 126
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title claims description 96
- 239000004014 plasticizer Substances 0.000 title claims description 70
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 title 2
- 150000001241 acetals Chemical class 0.000 claims description 103
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 76
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 72
- 125000003158 alcohol group Chemical group 0.000 claims description 34
- 239000011521 glass Substances 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 125000004036 acetal group Chemical group 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- -1 keto compound Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 229930194542 Keto Natural products 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000468 ketone group Chemical group 0.000 claims description 5
- 230000008021 deposition Effects 0.000 claims description 3
- 239000003981 vehicle Substances 0.000 claims description 2
- 239000003925 fat Substances 0.000 claims 1
- 239000010410 layer Substances 0.000 description 86
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 58
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 37
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 20
- 229920002689 polyvinyl acetate Polymers 0.000 description 14
- 239000011118 polyvinyl acetate Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 10
- 230000035515 penetration Effects 0.000 description 9
- 239000005336 safety glass Substances 0.000 description 9
- 238000006359 acetalization reaction Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000005340 laminated glass Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 3
- 230000000181 anti-adherent effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- OJXOOFXUHZAXLO-UHFFFAOYSA-M magnesium;1-bromo-3-methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC(Br)=C1 OJXOOFXUHZAXLO-UHFFFAOYSA-M 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- OLAQBFHDYFMSAJ-UHFFFAOYSA-L 1,2-bis(7-methyloctyl)cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCC1(C([O-])=O)CCCCC1(CCCCCCC(C)C)C([O-])=O OLAQBFHDYFMSAJ-UHFFFAOYSA-L 0.000 description 2
- GCDUWJFWXVRGSM-UHFFFAOYSA-N 2-[2-(2-heptanoyloxyethoxy)ethoxy]ethyl heptanoate Chemical compound CCCCCCC(=O)OCCOCCOCCOC(=O)CCCCCC GCDUWJFWXVRGSM-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- VVKREWPWSWPBGC-UHFFFAOYSA-N benzoic acid;2-(2-hydroxypropoxy)propan-1-ol Chemical compound CC(O)COC(C)CO.OC(=O)C1=CC=CC=C1 VVKREWPWSWPBGC-UHFFFAOYSA-N 0.000 description 2
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 2
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- GWQRPOCMBMQBTK-UHFFFAOYSA-N 2-[2-(2-ethylhexanoyloxy)ethoxy]ethyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCCOCCOC(=O)C(CC)CCCC GWQRPOCMBMQBTK-UHFFFAOYSA-N 0.000 description 1
- WPMUZECMAFLDQO-UHFFFAOYSA-N 2-[2-(2-hexanoyloxyethoxy)ethoxy]ethyl hexanoate Chemical compound CCCCCC(=O)OCCOCCOCCOC(=O)CCCCC WPMUZECMAFLDQO-UHFFFAOYSA-N 0.000 description 1
- JEYLQCXBYFQJRO-UHFFFAOYSA-N 2-[2-[2-(2-ethylbutanoyloxy)ethoxy]ethoxy]ethyl 2-ethylbutanoate Chemical compound CCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CC JEYLQCXBYFQJRO-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
- FZWOQNIYLGAJOA-UHFFFAOYSA-N 2-[2-[2-(7-methyloctanoyloxy)ethoxy]ethoxy]ethyl 7-methyloctanoate Chemical compound CC(C)CCCCCC(=O)OCCOCCOCCOC(=O)CCCCCC(C)C FZWOQNIYLGAJOA-UHFFFAOYSA-N 0.000 description 1
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 1
- BJIUNQZHYLBUNL-UHFFFAOYSA-N 6-heptoxy-6-oxohexanoic acid Chemical compound CCCCCCCOC(=O)CCCCC(O)=O BJIUNQZHYLBUNL-UHFFFAOYSA-N 0.000 description 1
- BYTZTSRYYDIWIH-UHFFFAOYSA-N 6-hexadecan-8-yloxy-6-oxohexanoic acid Chemical class CCCCCCCCC(CCCCCCC)OC(=O)CCCCC(O)=O BYTZTSRYYDIWIH-UHFFFAOYSA-N 0.000 description 1
- OIUGWVWLEGLAGH-UHFFFAOYSA-N 6-nonoxy-6-oxohexanoic acid Chemical compound CCCCCCCCCOC(=O)CCCCC(O)=O OIUGWVWLEGLAGH-UHFFFAOYSA-N 0.000 description 1
- SXKCDRRSQHPBOI-UHFFFAOYSA-N 6-o-cyclohexyl 1-o-hexyl hexanedioate Chemical compound CCCCCCOC(=O)CCCCC(=O)OC1CCCCC1 SXKCDRRSQHPBOI-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical compound C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001744 Polyaldehyde Polymers 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- HORIEOQXBKUKGQ-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCC(C)C HORIEOQXBKUKGQ-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000004806 diisononylester Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
-
- 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
- B32B17/10009—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 number, the constitution or treatment of glass sheets
- B32B17/10036—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 number, the constitution or treatment of glass sheets comprising two outer glass sheets
-
- 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
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
- B32B27/306—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising vinyl acetate or vinyl alcohol (co)polymers
-
- 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
- C08F8/28—Condensation with aldehydes or ketones
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/14—Homopolymers or copolymers of acetals or ketals obtained by polymerisation of unsaturated acetals or ketals or by after-treatment of polymers of unsaturated alcohols
-
- 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
- B32B2250/00—Layers arrangement
- B32B2250/03—3 layers
-
- 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
- B32B2250/00—Layers arrangement
- B32B2250/24—All layers being polymeric
- B32B2250/246—All polymers belonging to those covered by groups B32B27/32 and B32B27/30
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31627—Next to aldehyde or ketone condensation product
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31627—Next to aldehyde or ketone condensation product
- Y10T428/3163—Next to acetal of polymerized unsaturated alcohol [e.g., formal butyral, etc.]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31645—Next to addition polymer from unsaturated monomers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
- Y10T428/31946—Next to second aldehyde or ketone condensation product
Description
−A 少なくとも1の第1の可塑剤と、ポリビニル(イソ)アセタール基含分50〜80質量%及びポリビニルアルコール基含分10〜25質量%を有する第1のポリビニル(イソ)アセタールとを含有する、
−B 少なくとも1の第2の可塑剤と、ポリビニルアルコール基含分10〜25質量%を有するポリビニル(n)アセタールとを含有する、かつ
−部分シートC 少なくとも1の第3の可塑剤と、ポリビニル(イソ)アセタール基含分50〜80質量%及びポリビニルアルコール基含分10〜25質量%を有する第2のポリビニル(イソ)アセタールとを含有する。
−A 少なくとも1の第1の可塑剤と、ポリビニルアルコール基含分10〜25質量%を有する第1のポリビニル(n)アセタールとを含有する、
−B 少なくとも1の第2の可塑剤と、ポリビニル(イソ)アセタール基含分50〜80質量%及びポリビニルアルコール基含分10〜25質量%を有するポリビニル(イソ)アセタールとを含有する、かつ
−C 少なくとも1の第3の可塑剤と、ポリビニルアルコール基含分10〜25質量%を有する第2のポリビニル(n)アセタールとを含有する。
−A 少なくとも1の第1の可塑剤と、ポリビニル(イソ)アセタール基含分50〜80質量%及びポリビニルアルコール基含分10〜25質量%を有する第1のポリビニル(イソ)アセタールとを含有する、
−B 少なくとも1の第2の可塑剤と、ポリビニル(イソ)アセタール基含分50〜80質量%及びポリビニルアルコール基含分10〜25質量%を有する第2のポリビニル(イソ)アセタールとを含有する、かつ
−C 少なくとも1の第3の可塑剤と、ポリビニル(イソ)アセタール基含分50〜80質量%及びポリビニルアルコール基含分10〜25質量%を有する第3のポリビニル(イソ)アセタールとを含有する。
・ 多価の脂肪族又は芳香族の酸のエステル、例えばジアルキルアジパート、例えばジヘキシルアジパート、ジオクチルアジパート、ヘキシルシクロヘキシルアジパート、ヘプチルアジパートとノニルアジパートとの混合物、ジイソノニルアジパート、ヘプチルノニルアジパート並びにアジピン酸と環式脂肪族の又はエーテル結合を有するエステルアルコールとのエステル、ジアルキルセバカート、例えばジブチルセバカート並びにセバシン酸と環式脂肪族の又はエーテル結合を有するエステルアルコールのエステル、フタル酸のエステル、例えばブチルベンジルフタラート又はビス−2−ブトキシエチルフタラート、シクロヘキサンジカルボン酸のエステル、例えば1,2−シクロヘキサンジカルボン酸ジイソノニルエステル。
・ 多価の脂肪族又は芳香族のアルコール又はオリゴエーテルグリコールであって1又は複数の非分枝の又は分枝した脂肪族又は芳香族の置換基を有するもののエステル又はエーテル、例えば、ジ−、トリ−又はテトラグリコールと鎖状の又は分枝した脂肪族又は環式脂肪族のカルボン酸とのエステル。後者の群のための例としては、ジエチレングリコール−ビス−(2−エチルヘキサノアート)、トリエチレングリコール−ビス−(2−エチル−ヘキサノアート)、トリエチレングリコール−ビス(2−エチルブタノアート)、テトラ−エチレングリコール−ビス−n−ヘプタノアート、トリエチレングリコール−ビス−n−ヘプタノアート、トリエチレングリコール−ビス−n−ヘキサノアート、テトラエチレン−グリコールジメチルエーテル及び/又はジプロピレングリコールベンゾアートが利用できる。
・ 脂肪族又は芳香族のエステルアルコールのホスファート、例えばトリス(2−エチルヘキシル)ホスファート(TOF)、トリエチルホスファート、ジフェニル−2−エチルヘキシルホスファート及び/又はトリクレシルホスファート。
・ クエン酸、コハク酸及び/又はフマル酸のエステル。
PVBのポリビニルアルコール含有量及びポリビニルアセタート含有量の決定
ASTM D 1396−92に応じて行う。アセタール化度(=ブチラール含有量)は、ポリビニルアルコール含有量及びポリビニルアセタート含有量からASTM D 1396−92に応じて決定した合計から100に不足する分として算出可能である。質量%からmol%への換算は、当業者に公知の式に従って行う。
JIS K 6726に応じて行い、かつ、ポリビニルアセタールの製造に使用されるポリビニルアルコールの粘度平均から決定する。
シートの可塑剤含有量を、シートをエタノール中へ溶解させ、引き続き定量的ガスクロマトグラフィに供することより算出する。層の可塑剤含有量を算出するためには、多層シートを約1週間のコンディショニング期間後に、すなわち、可塑剤マイグレーションが十分終了した後に、再度分けて、個々に測定しなくてはならない。
シートの引裂強度及び破断点伸びのための値を、引張試験機械(TIRA社)を用いてISO 527に応じて200mm/minの速度で測定する。
球落下のための値の測定を、ECE43に応じて2.26kgの重さの鋼球を用いて寸法30×30cmかつ厚さ2mmのガラス板(この例において示したシートを含む)に対して行った。試験を10個のガラスサンプルに対してECE43に応じた温度及び空気湿度で行う。
可塑剤含有部分アセタール化ポリビニルアルコールをベースとするシートの付着の検証及び抗付着剤の作用の検査のために、いわゆるパンメル試験を適用し、この試験は文献においてある程度の変法で記載されている。本発明の範囲内で挙げられたパンメル値を、WO 03/033583 A1号公報に記載のパンメル試験を用いて測定した。
ミネラルガラスに対するPVBシートの付着の評価のために、いわゆる圧縮剪断試験(Kompressionsschertest)を次の説明に応じて実施する。試験体の製造のために、寸法300mm×300mm、厚さ4mmを有する2つの平らなシリカガラス板の間に試験すべきPVB接着シートを導入し、予備複合炉(Vorverbundofen)中でカレンダーロールを用いて脱気してガラス予備複合体にし、引き続きオートクレーブ中で圧力12barでかつ温度140℃で30分間プレスして、平らな合わせ安全ガラスにした。このように製造した合わせ安全ガラスから寸法25.4mm×25.4mmを有する10つの試料を切り出す。これらを45°の角度で2つの部分からなる試験装置へと挟み込む。この上側半分を、前記試験体の、すなわち、試験すべき合わせ安全ガラス板の内部で剪断剥がれ(Abscherung)が生じるまで、連続的に増加する、正確に垂直方向に下側へ指向させた力に曝露する。
ポリビニルアルコールMowiol 28−99(Kuraray Europe GmbHの市販品)100質量部を、90℃に加熱しながら、水975質量部中に溶解させた。温度40℃でn−ブチルアルデヒド57.5質量部を、そして、温度12℃で撹拌しながら20%の塩酸75質量部を添加した。この混合物をポリビニルブチラール(PVB)の沈殿後に73℃に加熱し、この温度で2時間撹拌した。室温へと冷却後にPVBを分離し、水で中性洗浄し、乾燥させた。ポリビニルアルコール含有量が20.3質量%であり、ポリビニルアセタート含有量が0.9質量%であるポリビニル(n)アセタールが得られた。
ポリビニルアルコールMowiol 28−99(Kuraray Europe GmbHの市販品)100質量部を、90℃に加熱しながら水975質量部中に溶解させた。温度40℃で、イソブチルアルデヒド57.6質量部を、そして、温度12℃で撹拌しながら20%の塩酸75質量部を添加した。この混合物をポリビニルブチラール(PVB)の沈殿後に73℃に加熱し、この温度で2時間撹拌した。室温へと冷却後にPVBを分離し、水で中性洗浄し、乾燥させた。ポリビニルアルコール含有量が20.3質量%であり、ポリビニルアセタート含有量が1.2質量%であるポリビニル(イソ)アセタールが得られた。
第1表及び第2表に応じた組成の部分層からシートを堆積(Zusammenlegen)により製造した。可塑剤としてトリエチレングリコール−2−エチルヘキサノアート(3G8)を使用した。この可塑剤含分は層の堆積の場合に同じであった。
PVA Iso−PVB A イソ−PVB部分層AのPVA含有量[質量%]
PVA Iso−PVB C イソ−PVB部分層CのPVA含有量[質量%]
PVA n−PVB B n−PVB部分層BのPVA含有量[質量%]
PVA n−PVB A n−PVB部分層AのPVA含有量[質量%]
PVA Iso−PVB B イソ−PVB部分層BのPVA含有量[質量%]
PVA n−PVB C n−PVB部分層CのPVA含有量[質量%]
厚さ Iso−PVB イソ−PVB部分層の層厚[mm]
厚さ n−PVB n−PVB部分層の層厚[mm]
付着 F/Sn CSS 圧縮剪断試験[N/mm2]
球落下 ECE43に応じた球落下、2mmガラス、 30×30cm、2.26kg球[落下高さ、m]
Mowiol 28−99 重合度1700を有するKuraray Euro pe GmbHの市販製品
Claims (12)
- 少なくとも1の可塑剤及び少なくとも1のポリビニルアセタールをそれぞれ含有する少なくとも3つの層A、B及びCから構築されているシート積層体において、
前記層A、B又はCの少なくとも1はポリビニルアセタールとして、平均重合度3000未満、ポリビニルアルコール基含分10〜25質量%及びポリビニル(イソ)アセタール基含分50〜80質量%を有する少なくとも1のポリビニル(イソ)アセタールを含有し、かつ、前記層Aと層Cの間に配置された層Bは32質量%未満の可塑剤含分を有することを特徴とするシート積層体。 - 前記層Bは、前記層A及び層C中のポリビニルアセタールのポリビニルアルコール基含分と同じか又はそれより多いポリビニルアルコール基含分を有するポリビニルアセタールを有することを特徴とする請求項1記載のシート積層体。
- 前記層A、B及びCの順序及び組成は次のとおりである:
−A 少なくとも1の第1の可塑剤と、ポリビニル(イソ)アセタール基含分50〜80質量%及びポリビニルアルコール基含分10〜25質量%を有する第1のポリビニル(イソ)アセタールとを含有する、
−B 少なくとも1の第2の可塑剤と、ポリビニルアルコール基含分10〜25質量%を有するポリビニル(n)アセタールとを含有する、かつ
−部分層C 少なくとも1の第3の可塑剤と、ポリビニル(イソ)アセタール基含分50〜80質量%及びポリビニルアルコール基含分10〜25質量%を有する第2のポリビニル(イソ)アセタールとを含有する、
ことを特徴とする請求項1又は2記載のシート積層体。 - 前記層A、B及びCの順序及び組成は次のとおりである:
−A 少なくとも1の第1の可塑剤と、ポリビニルアルコール基含分10〜25質量%を有する第1のポリビニル(n)アセタールとを含有する、
−B 少なくとも1の第2の可塑剤と、ポリビニル(イソ)アセタール基含分50〜80質量%及びポリビニルアルコール基含分10〜25質量%を有するポリビニル(イソ)アセタールとを含有する、かつ
−C 少なくとも1の第3の可塑剤と、ポリビニルアルコール基含分10〜25質量%を有する第2のポリビニル(n)アセタールとを含有する、
ことを特徴とする請求項1又は2記載のシート積層体。 - 前記層A、B及びCの順序及び組成は次のとおりである:
−A 少なくとも1の第1の可塑剤と、ポリビニル(イソ)アセタール基含分50〜80質量%及びポリビニルアルコール基含分10〜25質量%を有する第1のポリビニル(イソ)アセタールとを含有する、
−B 少なくとも1の第2の可塑剤と、ポリビニル(イソ)アセタール基含分50〜80質量%及びポリビニルアルコール基含分10〜25質量%を有する第2のポリビニル(イソ)アセタールとを含有する、かつ
−C 少なくとも1の第3の可塑剤と、ポリビニル(イソ)アセタール基含分50〜80質量%及びポリビニルアルコール基含分10〜25質量%を有する第3のポリビニル(イソ)アセタールとを含有する、
ことを特徴とする請求項1又は2記載のシート積層体。 - それぞれ互いに隣接する層が、多くとも10phr異なる可塑剤含有量を有することを特徴とする請求項1から5のいずれか1項記載のシート積層体。
- それぞれ互いに隣接する層が、ポリビニルアルコール基含分が多くとも2質量%異なるポリビニルアセタールを有することを特徴とする請求項1から6のいずれか1項記載のシート積層体。
- ポリビニル(イソ)アセタールが、少なくとも1のポリビニルアルコールと、4〜10個の炭素原子を有し、かつケト基に対してα位又はβ位にある少なくとも1の分枝を有する1又は複数の脂肪族ケト化合物との反応から得られることを特徴とする請求項1から7のいずれか1項記載のシート積層体。
- ポリビニル(n)アセタールが、少なくとも1のポリビニルアルコールと、2〜10個の炭素原子を有する1又は複数の非分枝の脂肪族ケト化合物との反応から得られることを特徴とする請求項1から4、6−8のいずれか1項記載のシート積層体。
- 層の共押出により製造されることを特徴とする請求項1から9のいずれか1項記載のシート積層体。
- 層の堆積により製造されることを特徴とする請求項1から9のいずれか1項記載のシート積層体。
- 自動車両、飛行機、船舶、建築物グレージング、ファサード部品用のガラス/シート積層体/ガラス−複合体の製造のための、又は光起電モジュールの製造のための請求項1から11のいずれか1項記載のシート積層体の使用。
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EP2548729A1 (de) * | 2011-07-22 | 2013-01-23 | Kuraray Europe GmbH | Folien aus weichmacherhaltigem Polyvinyl(iso)acetal |
EP2732968A1 (de) * | 2012-11-16 | 2014-05-21 | Kuraray Europe GmbH | Penetrationsfeste Mehrschichtfolien aus weichmacherhaltigem Polyvinylacetal mit schalldämpfenden Eigenschaften |
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JP2013022963A (ja) | 2013-02-04 |
CN103029394A (zh) | 2013-04-10 |
EP2548731B1 (de) | 2014-09-03 |
KR101966405B1 (ko) | 2019-04-05 |
EP2548731A1 (de) | 2013-01-23 |
RU2588632C2 (ru) | 2016-07-10 |
US20130022824A1 (en) | 2013-01-24 |
CN103029394B (zh) | 2016-08-03 |
RU2012128576A (ru) | 2014-01-20 |
EP2548727A1 (de) | 2013-01-23 |
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