EP4204225A1 - Films minces comprenant des acétals de vinyle-éthylène - Google Patents
Films minces comprenant des acétals de vinyle-éthylèneInfo
- Publication number
- EP4204225A1 EP4204225A1 EP21777549.3A EP21777549A EP4204225A1 EP 4204225 A1 EP4204225 A1 EP 4204225A1 EP 21777549 A EP21777549 A EP 21777549A EP 4204225 A1 EP4204225 A1 EP 4204225A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- interlayer film
- film according
- ethylene vinyl
- glass
- interlayer
- 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.)
- Pending
Links
- 239000005977 Ethylene Substances 0.000 title claims abstract description 45
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 45
- -1 ethylene vinyl acetals Chemical class 0.000 title claims abstract description 35
- 239000010409 thin film Substances 0.000 title description 2
- 239000011229 interlayer Substances 0.000 claims abstract description 80
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000004014 plasticizer Substances 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims description 28
- 239000002245 particle Substances 0.000 claims description 27
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 19
- 239000006096 absorbing agent Substances 0.000 claims description 19
- 239000011521 glass Substances 0.000 claims description 19
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 17
- 239000005340 laminated glass Substances 0.000 claims description 13
- 238000000149 argon plasma sintering Methods 0.000 claims description 12
- 239000000049 pigment Substances 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 10
- 239000010410 layer Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000004744 fabric Substances 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 239000002313 adhesive film Substances 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- 238000003475 lamination Methods 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 2
- 239000012943 hotmelt Substances 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 239000010408 film Substances 0.000 description 83
- 238000001125 extrusion Methods 0.000 description 14
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 13
- 238000006359 acetalization reaction Methods 0.000 description 13
- 150000001241 acetals Chemical class 0.000 description 12
- 238000007639 printing Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 7
- 239000011354 acetal resin Substances 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 239000004715 ethylene vinyl alcohol Substances 0.000 description 6
- 239000000976 ink Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 125000004036 acetal group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000002105 nanoparticle Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 4
- 238000010030 laminating Methods 0.000 description 4
- 238000001429 visible spectrum Methods 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229910021393 carbon nanotube Inorganic materials 0.000 description 3
- 239000002041 carbon nanotube Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 125000003010 ionic group Chemical group 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
- 239000011159 matrix material Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229940044613 1-propanol Drugs 0.000 description 2
- BOHKXQAJUVXBDQ-UHFFFAOYSA-N 2,3-dimethylpentanal Chemical compound CCC(C)C(C)C=O BOHKXQAJUVXBDQ-UHFFFAOYSA-N 0.000 description 2
- OYFRNYNHAZOYNF-UHFFFAOYSA-N 2,5-dihydroxyterephthalic acid Chemical compound OC(=O)C1=CC(O)=C(C(O)=O)C=C1O OYFRNYNHAZOYNF-UHFFFAOYSA-N 0.000 description 2
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- XMVBHZBLHNOQON-UHFFFAOYSA-N 2-butyl-1-octanol Chemical compound CCCCCCC(CO)CCCC XMVBHZBLHNOQON-UHFFFAOYSA-N 0.000 description 2
- JGEGJYXHCFUMJF-UHFFFAOYSA-N 4-methylpentanal Chemical compound CC(C)CCC=O JGEGJYXHCFUMJF-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 239000003513 alkali Substances 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
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 239000004806 diisononylester Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 235000019256 formaldehyde Nutrition 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910021389 graphene Inorganic materials 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000007561 laser diffraction method Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000000414 obstructive effect Effects 0.000 description 2
- 150000002979 perylenes Chemical class 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 2
- JMPMXZYKZRDYCH-BOPFTXTBSA-N (3z)-3-(quinolin-2-ylmethylidene)isoindol-1-one Chemical compound C12=CC=CC=C2C(=O)N\C1=C/C1=CC=C(C=CC=C2)C2=N1 JMPMXZYKZRDYCH-BOPFTXTBSA-N 0.000 description 1
- BHVGMUDWABJNRC-UHFFFAOYSA-N (±)-2-methylhexanal Chemical compound CCCCC(C)C=O BHVGMUDWABJNRC-UHFFFAOYSA-N 0.000 description 1
- KEQXNNJHMWSZHK-UHFFFAOYSA-L 1,3,2,4$l^{2}-dioxathiaplumbetane 2,2-dioxide Chemical compound [Pb+2].[O-]S([O-])(=O)=O KEQXNNJHMWSZHK-UHFFFAOYSA-L 0.000 description 1
- QYPLKDUOPJZROX-UHFFFAOYSA-N 2,2-dimethylbutanal Chemical compound CCC(C)(C)C=O QYPLKDUOPJZROX-UHFFFAOYSA-N 0.000 description 1
- YMXAGOUPXPGFLB-UHFFFAOYSA-N 2,2-dimethylpentanal Chemical compound CCCC(C)(C)C=O YMXAGOUPXPGFLB-UHFFFAOYSA-N 0.000 description 1
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 1
- AKUUEDVRXOZTBF-UHFFFAOYSA-N 2,3-dimethylbutanal Chemical compound CC(C)C(C)C=O AKUUEDVRXOZTBF-UHFFFAOYSA-N 0.000 description 1
- GPTMCJMLSOIYGU-UHFFFAOYSA-N 2,4-dimethylpentanal Chemical compound CC(C)CC(C)C=O GPTMCJMLSOIYGU-UHFFFAOYSA-N 0.000 description 1
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 1
- YHCGGLXPGFJNCO-UHFFFAOYSA-N 2-(2H-benzotriazol-4-yl)phenol Chemical class OC1=CC=CC=C1C1=CC=CC2=C1N=NN2 YHCGGLXPGFJNCO-UHFFFAOYSA-N 0.000 description 1
- LEVFXWNQQSSNAC-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxyphenol Chemical compound OC1=CC(OCCCCCC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 LEVFXWNQQSSNAC-UHFFFAOYSA-N 0.000 description 1
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 1
- BFKSYXOOFDWKFF-UHFFFAOYSA-N 2-ethyl-2-methylbutanal Chemical compound CCC(C)(CC)C=O BFKSYXOOFDWKFF-UHFFFAOYSA-N 0.000 description 1
- SHGPBDQRELYPLO-UHFFFAOYSA-N 2-ethyl-3-methylbutanal Chemical compound CCC(C=O)C(C)C SHGPBDQRELYPLO-UHFFFAOYSA-N 0.000 description 1
- OZGRFPZYTKHWMZ-UHFFFAOYSA-N 2-ethylpentanal Chemical compound CCCC(CC)C=O OZGRFPZYTKHWMZ-UHFFFAOYSA-N 0.000 description 1
- AXIZYEUPVXWMSV-UHFFFAOYSA-N 2-methylbutanal pentan-2-one Chemical compound CC(C=O)CC.C(C)(CCC)=O AXIZYEUPVXWMSV-UHFFFAOYSA-N 0.000 description 1
- LTNUSYNQZJZUSY-UHFFFAOYSA-N 3,3-dimethylbutanal Chemical compound CC(C)(C)CC=O LTNUSYNQZJZUSY-UHFFFAOYSA-N 0.000 description 1
- HPKCSWORDUPIJS-UHFFFAOYSA-N 3,3-dimethylpentanal Chemical compound CCC(C)(C)CC=O HPKCSWORDUPIJS-UHFFFAOYSA-N 0.000 description 1
- SZBNDYYJXRXQHA-UHFFFAOYSA-N 3,4-dimethylpentanal Chemical compound CC(C)C(C)CC=O SZBNDYYJXRXQHA-UHFFFAOYSA-N 0.000 description 1
- ZSJUABCTGCNBPF-UHFFFAOYSA-N 3-Methylhexanal Chemical compound CCCC(C)CC=O ZSJUABCTGCNBPF-UHFFFAOYSA-N 0.000 description 1
- XKJUKVTZSPIGSI-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O.CC(C)CC=O XKJUKVTZSPIGSI-UHFFFAOYSA-N 0.000 description 1
- YJWJGLQYQJGEEP-UHFFFAOYSA-N 3-methylpentanal Chemical compound CCC(C)CC=O YJWJGLQYQJGEEP-UHFFFAOYSA-N 0.000 description 1
- DZWACSVTJIDBDB-UHFFFAOYSA-N 4,4-dimethylpentanal Chemical compound CC(C)(C)CCC=O DZWACSVTJIDBDB-UHFFFAOYSA-N 0.000 description 1
- HYPVVALCENOWNK-UHFFFAOYSA-N 4-(2,3-diphenylphenyl)-2H-triazin-5-one Chemical class C1(=CC=CC=C1)C=1C(=C(C=CC=1)C1=NN=NC=C1O)C1=CC=CC=C1 HYPVVALCENOWNK-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- GIGNTOMJQYNUNL-UHFFFAOYSA-N 4-methylhexanal Chemical compound CCC(C)CCC=O GIGNTOMJQYNUNL-UHFFFAOYSA-N 0.000 description 1
- YUXBNNVWBUTOQZ-UHFFFAOYSA-N 4-phenyltriazine Chemical class C1=CC=CC=C1C1=CC=NN=N1 YUXBNNVWBUTOQZ-UHFFFAOYSA-N 0.000 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- GEKRISJWBAIIAA-UHFFFAOYSA-N 5-methylhexanal Chemical compound CC(C)CCCC=O GEKRISJWBAIIAA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- JVOAOAWSRNKZPU-UHFFFAOYSA-N CNC(=O)C1=C(C2=C3C(=C1)C=CC=C3C4=CC=CC5=C4C2=CC=C5)C(=O)NC Chemical compound CNC(=O)C1=C(C2=C3C(=C1)C=CC=C3C4=CC=CC5=C4C2=CC=C5)C(=O)NC JVOAOAWSRNKZPU-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
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- 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
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- PMPJQLCPEQFEJW-HPKCLRQXSA-L disodium;2-[(e)-2-[4-[4-[(e)-2-(2-sulfonatophenyl)ethenyl]phenyl]phenyl]ethenyl]benzenesulfonate Chemical group [Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC=C1\C=C\C1=CC=C(C=2C=CC(\C=C\C=3C(=CC=CC=3)S([O-])(=O)=O)=CC=2)C=C1 PMPJQLCPEQFEJW-HPKCLRQXSA-L 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
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- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
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- 235000013980 iron oxide Nutrition 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
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- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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Definitions
- the invention is directed to interlayer films with a low thickness comprising an ethylene vinyl acetal and optionally at least one plasticiser.
- Interlayer films comprising polyvinyl acetal are long known as adhesive layer for laminating glass, polymers or fibres.
- plasticized polyvinyl butyral (PVB) films are widely used as adhesive layer for glass-glass laminates, e.g. for windshields in automotive use.
- Said films are often used to introduce various functionalities into the windshield. For example, compounds that effectively shield from UV or IR rays can be introduced.
- a further functionality is the introduction of fluorophores to display information on the inside of the vehicle (so-called head-up-displays).
- head-up-displays it is also known to use an interlayer film which is non-transparent to visible light in certain regions of the windshield in order to protect the sealing or adhesives from UV radiation or to hide sensor systems from being seen from the outside of the car.
- Such functionalizations are often introduced by means of thin plastic films which are used in combination with the common plasticized PVB films.
- IR- shielding particles can be coated onto PET films as described in US 2011/00767473 and then used together with common plasticized PVB interlayer films.
- thin non-plasticised PVB films or patches as carriers for various functionalities, e.g. printed obscuration areas or I R-shielding patches, as for example disclosed in WO 2019/038043 A1 .
- PET cannot be melted directly to a glass surface and thus, needs to be sandwiched between two PVB layers in order to function as interlayer film for laminated glass.
- Another disadvantage of the PVB usually used for such applications is its inherently high viscosity, which makes it difficult to extrude.
- the high viscosity requires high extrusion- and melt temperatures which accelerate the degradation reactions and therefore negatively influence optical (e.g. yellowness) and mechanical (e.g. tensile strength) properties.
- optical e.g. yellowness
- mechanical e.g. tensile strength
- a potential solution to decrease viscosity at extrusion temperature is to add plasticizer.
- interlayer films having advantageous properties.
- interlayer films with a low thickness comprising an ethylene vinyl acetal and optionally at least one plasticiser can solve some of the disadvantages of the films of the prior art.
- one objective of the invention is to provide interlayer films with an improved material, e.g. using a material with improved production costs or raw material costs and/or an improved environmental footprint.
- Another objective of the present invention is to provide interlayer films with improved characteristics like improved thermal stability, improved melting point, improved viscosity, improved water uptake profile, improved compatibility with other components, e.g. glass, PVB interlayers, fibres, pigments and/or dyes.
- Another objective of the present invention is to provide interlayer films with improved characteristics, e.g. an improved processibility in film making and/ transportation.
- Yet another objective is to provide interlayer films with a low viscosity at extrusion temperature and improved stiffness in a temperature range between 20 °C and 100 °C.
- the present invention provides an interlayer film comprising an ethylene vinyl acetal and optionally at least one plasticiser wherein the thickness of the interlayer film is from 5 to 95 pm, preferably from 10 to 75 pm, more preferably from 20 to 55 pm.
- Figure 1 Complex viscosity as a function of angular frequency at 190 °C
- the ethylene vinyl acetal of the present invention can be obtained by subjecting an aldehyde to an acetalization reaction with an ethylene vinyl alcohol (EVOH).
- EVOH ethylene vinyl alcohol
- Such ethylene vinyl alcohols are known in the art and can be obtained by copolymerizing ethylene in the presence of an acidic catalyst. Furthermore, ethylene vinyl alcohols are commercially available.
- the ethylene vinyl alcohol is obtained by copolymerizing ethylene and a vinyl acetate and hydrolysing the obtained copolymer.
- a conventionally known alkali catalyst or an acid catalyst can be used and among them, a hydrolysation reaction using methanol as a solvent and caustic soda (NaOH) catalyst is convenient.
- the method for producing the ethylene vinyl acetals used in this embodiment of the present invention can be produced by a method in which an aldehyde is added to the ethylene vinyl alcohol solution under acidic conditions and subjected to the acetalization reaction.
- the reaction product obtained after the acetalization reaction is neutralized with alkali, and then washed with water to obtain the ethylene vinyl acetal.
- the catalyst for carrying out the acetalization reaction is not particularly limited, and any organic acid or inorganic acid may be used. Examples thereof include acetic acid, para toluenesulfonic acid, nitric acid, sulfuric acid, hydrochloric acid, carbonic acid, and the like.
- the interlayer film is provided with an obscuration area wherein the obscuration area is printed or coated onto at least one surface of the interlayer film or wherein the obscuration area is provided by a dye or a pigment dispersed in the interlayer film. More preferably, the obscuration area has at least one transparent area embedded in the obscuration area.
- obscuration area refers to any region of the laminate having a light transmission in the visible spectrum of less than 5%.
- the obscuration area may fade out towards transparency.
- at least a part of the obscuration area of the laminate has a light transmission in the visible spectrum of less than 5%.
- obscuration area having at least one transparent area refers to one or more region of the laminate having a reduced light transmission as defined above, with transparent areas embedded therein.
- the transparent areas have preferable a light transmission in the visible spectrum not less than the rest of the laminate which is not covered by an obscuration area.
- the transparent areas may be used as viewing areas for optical detection devices positioned behind the transparent areas in the final windshield.
- Optical detection devices include digital cameras, range finders, haze meters, rain sensors, target detectors, scanning laser devices (LIDAR) or related devices using electromagnetic radiation from within the UV/VIS and NIR/IR range of the spectrum.
- the obscuration area may be provided by a printed or coated layer on at least one surface of the interlayer film.
- pigments preferable carbon black, iron oxides, polyaniline, perylenes or spinel pigments are used.
- the pigments may be dispersed in a carrier fluid like water, alcohol or mixtures of alcohol and water.
- binders like polyvinylalcohol, polyvinylbutyral, polyvinylpyrrolidone, polyacrylates, polyurethanes or poly styreneacrylate may be present.
- Such printing compositions are referred to as “printing inks” or simple “inks” hereinafter.
- the printing inks can be applied via techniques that are commonly known in the printing industry such as offset printing, rotogravure printing, flexography, and screen-printing, followed usually by a drying step.
- the pigments can be dispersed in the ethylene vinyl acetal films, e.g. a pigment is added to the ethylene vinyl acetal before or during the film production process.
- the obscuration area can be completely opaque and/or in part interrupted and/or have a transition area from a completely opaque edge into the transparent area.
- the dry-film thickness of the ink/pigment layer in the obscuration area is from 1 to 50 pm. Usually the dry-film thickness is from 10 to 30 pm. High enough total dry-film thicknesses can be achieved by overlaying inklayers through repetition of sequential printing / coating steps.
- the obscuration area has at least one area with a transmission in the visible spectrum from 380 nm to 740 nm of less than 20%, more preferably 10% and most preferably less than 5%. Also preferably, the obscuration area has an L* value in the L,a,b system of less than 10, more preferably less than 5, even more preferably less than 2.5. The obscuration area may appear grey or black.
- At least one area in the obscuration area is obscure to visible light but has a transmission for infrared radiation from 850 nm to 1200 nm of more than 70%, more preferably more than 80% and even more preferably more than 90%.
- Black pigments such as perylene pigments are particularly suitable for this embodiment.
- Perylene pigments are known with many substitution patterns, e.g. from DE 102004007382 A1 , and are used as paint additive and dye for polymers.
- N,N'- dimethylperylenedicarboxylic acid diimide MPTCDI
- PTCDA perylene tetracarboxylic acid dianhydride
- the interlayer film is provided with IR shielding particles wherein the IR shielding particles are printed or coated onto at least one surface of the interlayer film or wherein the IR shielding particles are dispersed in the interlayer film.
- the IR shielding particles can be chosen from ITO, ATO, AZO, IZO, zinc antimonates, tin-doped zinc oxide, silicon-doped zinc oxide, gallium-doped zinc oxide, tungstates, such as LiWO3, NaWO3, CsWO3, lanthanum hexaboride and cerium hexaboride.
- the IR shielding particles preferably have a mean diameter from 5 to 500 nm, i.e. they are so-called nanoparticles.
- the proportion of IR shielding particles in or on the interlayer film may be from 1 to 20 % by weight, preferably from 2 to 10 % by weight.
- the interlayer film is provided with a fluorophore wherein the fluorophore is printed or coated onto at least one surface of the interlayer film or wherein the fluorophore is dispersed in the interlayer film.
- the excitation of the fluorophores used according to the invention is preferably done through radiation in the non-visible range of light, such as in the wavelength range of 300-420 nm, preferably in the wavelength range of 350-400 nm and most preferably in the wavelength range of 365-385 nm.
- UV lasers or UV-LEDs can particularly be used as a radiation source.
- fluorophores can be advantageously used: fluorescing inorganic nanoparticles, fluorescent dyes that are poorly soluble in the surrounding matrix, such as substituted perylenes or rylenes or derivatives of quinacridone, fluorescent dyes with ionic groups such as Tinopal CBS-X or of an ionic nature such as uranine, as well as polymeric fluorophores.
- fluorescent dyes with ionic groups such as Tinopal CBS-X or of an ionic nature such as uranine
- polymeric fluorophores Especially preferred are 2,5-dihydroxyterephthalic acid and 3-(2-quinolylmethylene)phthalimidine and they can be present in the interlayer film in an amount of from 0.001 to 5 % by weight.
- the interlayer film is provided with light scattering particles wherein the light scattering particles are printed or coated onto at least one surface of the interlayer film or wherein the light scattering particles are dispersed in the interlayer film.
- the light scattering particles are chosen from the group consisting of TiO2, ZnO, AI2O3, ZrO2, PbSO4, BaSO4, CaCO3, glass, polymers and mixtures thereof.
- the light scattering particles can be used as solid or hollow beads or fibres.
- the light scattering particles are present in the interlayer film in an amount of 0.1 to 10 % by weight, more preferred 0.5 to 5 % by weight, most preferably 1 to 2.5 % by weight.
- the light scattering particles have a median particle size D50 by volume determined by the laser diffraction method according to DIN 13320 of equal to or more than 0.001 , more preferably 0.01 pm, 0.05 pm or 0.1 pm. Also preferably they are equal to or less than 10.0 pm, more preferably 5.0 pm and most preferably 1 .0 pm.
- the median particle size by volume determined by the laser diffraction method according to DIN 13320 is equal to or more than 0.01 pm and equal to or less than 1 .0 pm.
- the interlayer film is provided with a UV absorber wherein the UV absorber is printed or coated onto at least one surface of the interlayer film or wherein the UV absorber is dispersed in the interlayer film.
- UV absorber is done in accordance with the method as described above for the obscuration area.
- the inventive interlayer films contain a UV absorber in a quantity of 0.005-5 % by weight, preferably 0.1 to 2.0, more preferably 0.2 to 1 .0 and most preferably 0.1 to 0.8 % by weight, each with respect to the weight of the layer in which the UV absorbers are contained.
- Low-molecular weight UV absorbers or UV absorbers with a low tendency to migrate or diffuse that are known for plasticizer-containing polyvinyl acetal films can be used as UV absorbers.
- an arrangement with another layer containing fluorophores makes it possible to have the fluorophores be excited by UV radiation from the passenger compartment without the radiation actually provided for excitation already being absorbed by the UV absorber.
- compounds of the benzotriazole type such as, for instance, Tinuvin P, Tinuvin 328, Tinuvin 326, Tinuvin 327 or substituted phenyltriazines Tinuvin 1577 or Cyasorb 1164 can be used.
- nanoparticles such as nano-TiO2, UV-absorbing polymers, UV absorbers that are poorly soluble in the present matrix of plasticizer and polyvinyl acetal, e.g., of the benzoxazinone type, the weakly substituted diphenyl hydroxyphenyltriazine type, UV absorbers containing ionic groups, UV absorbers chemically linked to the polyvinyl acetal, e.g., those based on benzotriazole, polymer- bound crylene or alkoxycrylene groups, particularly those with an alkoxy group in one of the phenyl rings such as those disclosed in U.S. Pat. No. 7,964,245 B2, for example, UV-absorbing polymers such as those cited in U.S. Pat. No. 7,008,618 B1 , or substituted 2-hydroxyphenyl benzotriazoles that are linked, for example, by an ester group to a polymer, particularly to a polyvinyl acetal.
- UV absorbers with a low tendency to migrate or diffuse cab be used, for example, Polyacrylene S1 by Hallstar, UV absorbers with ionic groups, UV-absorbing nanoparticles, or organic UV absorbers present as particles in the film matrix.
- the interlayer film is provided with a plurality of electrically conductive wires on at least one surface of the interlayer film.
- Electrode conductive wires shall mean discrete, electrically conductive structures that do not comprise flat layers but separately identifiable structures such as conductor tracks, wires, networks built with these tracks or wires, dots, and combinations thereof.
- the discrete electrically conductive structures comprise metals such as silver, copper, gold, indium, zinc, iron, and aluminum.
- semiconductor materials or carbon-based conductive materials such as graphite, CNT (carbon nanotubes) or graphene, can be used.
- the electrically conductive structures can be generated by different types of printing processes such as screen printing, flexoprinting or gravure printing, vapor deposition, sputtering, or electrodeposition on the surface of film A.
- printing processes corresponding inks are used which can be dried, or thermally or photonically cured before lamination.
- the inks or printing colors used contain conductive particles. These may be particles composed of metals such as gold, silver, copper, zinc, iron or aluminum, as well as metal-coated materials such as silver plated glass fibers, glass beads and conductive carbon black, carbon nanotubes, graphite or graphene.
- the electrically conductive structures can generally be used for electromagnetic shielding of frequency fields, for generating electrical circuits such as printed circuit tracks or transmitting and/or receiving antennas, as well as other functions.
- Heaters can, for instance, be incorporated in the glass composite, antennas can, for example, be used in the automotive sector for receiving radio waves or in car-to-car communication.
- the electrically conductive structures of the laminates according to the invention can also be composed of touch sensors, which enables the production of interactive laminated glass panes.
- information input to the laminated glass pane for example, a windshield or side window of a car or the sliding glass of a door
- multilayer structures of electronic elements i.e. conductive and dielectric structures
- whole electronic circuits or components can be further applied.
- These include, inter alia, transistors, resistors, chips, sensors, displays, light emitting diodes (OLEDs, for example) and/or smart labels.
- the electrically conductive structures may be so small that they can only be barely recognized with the naked eye. This happens at widths of 1 to 30 pm, preferably 1 to 20 pm, and most preferably 1 to 15 pm. In particular, in flat heating fields, the width of the filaments is less than 25 pm. Heating panels can also be applied only locally, on an upper surface of a windshield in front of an optical sensor system, for example.
- the degree of saponification of the acetate groups is preferably 95 mol% or more, more preferably 98 mol% or more, still more preferably 99 mol% or more, and most preferably 99.9 mol% or more.
- the percentage of ethylene units in the ethylene vinyl alcohol is 25 to 60 mol%, more preferably 30 to 55 mol%, and still more preferably 35 to 50 mol%.
- the percentage of ethylene units in the ethylene vinyl acetal is 25 to
- the percentage of vinyl alcohol units in the ethylene vinyl acetal resin of the present invention is 24 to 71 mol% based on the total monomer units constituting the resin.
- the degree of acetalization of the ethylene vinyl acetal used in the present invention is from 1 mol% to 80 mol%, also preferably 5 mol% or more and less than 40 mol%, more preferably the lower limit of the degree of acetalization is more than 6 mol%, more than 7 mol%, more than 8 mol%, more than 9 mol%, and most preferably more than 10 mol%.
- the upper limit of the degree of acetalization is more preferably 38 mol% or less, 36 mol% or less, 34 mol% or less, and 32 mol% or less in this order, and most preferably less than 30 mol%.
- Another preferred degree of acetalization is from 30 to 50 mol%.
- the acetal groups individually have 1 to 7 carbon atoms, i.e. they derive from the condensation reaction with aldehydes with 1 to 7 carbon atoms. More preferably, they derive from the list consisting of methanal (formaldehyde), acetaldehyde, n-propanal (propionaldehyde), n-butanal (butyraldehyde), iso-butanal (2-methyl-1 -propanal, iso-butyraldehyde), n-pentanal (valeraldeyhde), iso-pentanal (3-methyl-1 -butanal), sec-pentanal (2-methyl-1 -butanal), tert-pentanal (2,2,dimethyl- 1 -propanal), n-hexanal (capronaldehyde), iso-hexanal (2-methyl-1 -pentanal, 3- methyl-1 -pentanal, 4-methyl-1 -
- the ethylene vinyl acetals are mixed acetals, i.e. they comprise at least two different acetal groups.
- the ethylene vinyl acetals as used in the invention comprise a first acetal group derived from the reaction of two hydroxyl groups of the respective ethylene vinyl alcohol with one aldehyde and at least a second acetal group derived from the reaction of two other hydroxyl groups of the respective ethylene vinyl alcohol with a second aldehyde, wherein the first aldehyde is different from the second aldehyde.
- the preferred aldehydes are the same as used for the acetals with one acetal group as listed above.
- the ethylene vinyl acetals used in the inventive process have a glass transition temperature (Tg) of equal to or higher than 30, 35, 40, 45, or 50 Q C. Also preferably, they have a Tg of 90, 75, 70, 65, 60, 55 -C. Also preferably, the ethylene vinyl acetals used in the inventive process have a Tg of 30 to 90 -C, more preferably 35 to 75 Q C, most preferably of 40 to 55 Q C.
- Tg glass transition temperature
- the glass transition temperature is determined by means of differential scanning calorimetry (DSC) in accordance with DIN 53765 using a heating rate of 10K/min at a temperature interval of minus 50 °C to 200 °C. A first heating ramp, followed by a cooling ramp, followed by a second heating ramp was used. The position of the glass transition temperature was established on the measurement curve associated with the second heating ramp in accordance with DIN 51007.
- the DIN midpoint (Tg DIN) was defined as the point of intersection of a horizontal line at half step height with the measurement curve.
- the step height was defined by the vertical distance of the two points of intersection of the middle tangent with the base lines of the measurement curve before and after glass transition.
- the melting point (melt temperature, Tm) is determined by means of differential scanning calorimetry (DSC) in accordance with DIN EN ISO 11357-3:2018.
- the vinyl alcohol content and vinyl acetate content of ethylene vinyl acetals were determined in accordance with DIN ISO 3681 (acetate content) and DIN ISO 53240 (PVA content).
- the vinyl acetal content can be calculated as the remaining portion from the sum of vinyl alcohol content and vinyl acetate content determined in accordance with DIN ISO 53401/53240 and the ethylene needed to make one hundred.
- the degree of acetalisation can be calculated from the amount of vinyl acetal content divided by the sum of vinyl alcohol content, vinyl acetal content and vinyl acetate content. Conversion from % by weight into mol % is achieved by formulas known to the person skilled in the art.
- the ethylene content of the ethylene vinyl acetal resin is measured by NMR spectroscopy.
- the ethylene vinyl acetal resin is dissolved in ethanol and a 2 N hydrochloride hydroxylamine solution and hydrochloric acid are added, and the mixture is stirred under reflux with a condenser in a water bath for 4 hours, and after cooling, ammonia water is added. Afterwards, methanol is added and the polymer is precipitated, washed and dried to obtain the ethylene vinyl alcohol copolymer.
- the ethylene vinyl alcohol copolymer is dissolved in DMSO (dimethyl sulfoxide) at 120 °C, cooled to room temperature, and then N,N-dimethyl-4-aminopyridine and acetic anhydride are added thereto, followed by stirring for 1 h, followed by precipitation with ion-exchanged water and acetone, and drying to obtain an ethylene vinyl acetate copolymer.
- DMSO dimethyl sulfoxide
- N,N-dimethyl-4-aminopyridine and acetic anhydride are added thereto, followed by stirring for 1 h, followed by precipitation with ion-exchanged water and acetone, and drying to obtain an ethylene vinyl acetate copolymer.
- the polymer is dissolved in DMSO-d6 and measured by a proton NMR spectrometer of 400 MHz. The spectrum obtained was integrated 256 times.
- the molar ratio of the ethylene units of the ethylene vinyl alcohol copolymer is calculated from the intensity ratio of the methine proton (peak of 1 .1 to 1 .9 ppm) derived from the ethylene unit and the vinyl acetate unit, and the terminal methyl proton (peak of 2.0 ppm) derived from the vinyl acetate unit. Note that, since the ethylene unit is not affected by the acetalization reaction, the molar ratio (n) of the ethylene unit of the ethylene vinyl alcohol copolymer before the acetalization reaction is equal to the molar ratio (n) of the ethylene unit of the ethylene vinyl acetal resin obtained after the acetalization reaction.
- the interlayer film according to the present invention comprises, other than the ethylene vinyl acetal, up to 20% by weight (based on the total weight of the composition) of one or more plasticizers. Any compound known to plasticize ethylene vinyl acetals may be used.
- Preferred plasticisers are diesters of aliphatic diols, in particular of aliphatic polyether diols and/or polyether polyols with aliphatic carboxylic acids, preferably diesters of polyalkylene oxides, in particular diesters of diethylene glycol, triethylene glycol and tetraethylene glycol with aliphatic (C6-C10) carboxylic acids, preferably 2-ethyl butyric acid and n-heptanoic acid, also diesters of aliphatic or aromatic (C2-C18) dicarboxylic acids, preferably adipine, sebacine and phthalic acid, with aliphatic (C4-C12) alcohols, preferably dihexyl adipate, phthalates, trimellitates, phosphates, fatty acid esters, in particular triethylene glycol-bis-(2-ethy I butyrate), triethylene glycol ethyl hexanoate (3G8), aromatic carboxylic
- plasticizers are ISOFOL 12+5 EO, a 2-butyloctanol with an average degree of ethoxylation of 5, dihexyladipate (DHA), 1 ,2- cyclohexandicarbonsaure- diisononylester (DINCH), dipropylene glycol dibenzoate (DPGDB), diethylene glycol dibenzoate (MONOCIZER PB-3A), MONOCIZER PB-10 and mixtures thereof.
- DHA dihexyladipate
- DICH dipropylene glycol dibenzoate
- DPGDB dipropylene glycol dibenzoate
- MONOCIZER PB-3A diethylene glycol dibenzoate
- MONOCIZER PB-10 MONOCIZER PB-10 and mixtures thereof.
- the interlayer film according tom the present invention comprises other components than the ethylene vinyl acetals as described above.
- it may contain antioxidants, optical brighteners, stabilisers, processing aids, organic or inorganic nanoparticles, pyrogenic silicic acid, silica, surface-active substances and/or rheological modifiers.
- a starting resin composition may be formed into a film by extrusion, blow molding, injection molding, solution casting or the like, preferably by extrusion.
- the resin temperature at the time of extrusion is preferably 170 to 250 °C, more preferably 180 to 240 °C, and still more preferably 190 to 230 °C. If the resin temperature becomes too high, the ethylene vinyl acetal resin undergoes partial decomposition.
- the extrusion process can be followed by a mono- or biaxial stretching process in order to increase mechanical properties (Young’s-Modulus, tensile strength).
- the film is pre-heated to a temperature between the glass transition temperature and the melting temperature, particularly between the glass transition temperature and the cold crystallization temperature.
- the biaxial-stretching process can be performed simultaneously or by a two-step process. For a two-step process, the temperature in machine and transversal direction can be adjusted independently.
- the stretching factor is below 4.
- the stretched film is heatset at a temperature between the cold crystallization temperature and the melting temperature.
- the interlayer films according to the invention have a certain roughness on at least one surface in order to prevent the interlayer films adhering to each other, e.g. when the film is wound up to a roll, and to enhance the degassing property in a laminating step.
- Conventional methods can be used to provide said roughness. Examples thereof include a method of providing a melt fracture structure by adjusting the extrusion conditions or embossing the surface. As for the depth and shape of the emboss, conventionally known ones may be used.
- a further aspect of the present invention concerns the use of the inventive interlayer film as adhesive film for laminated glass. Due to the low thickness of the inventive interlayer films, they are generally combined with a commercially available standard PVB interlayer film such as the Trosifol® range of interlayers for laminated glass.
- Yet another aspect of the present invention concerns a laminated glass comprising two sheets of glass combined by an adhesive film comprising at least one interlayer film according to the invention and at least one film containing a polyvinyl acetal and at least one plasticiser.
- the at least one film containing a polyvinyl acetal is any plasticized PVB-film known in the art. It may contain a single plasticiser as well as mixtures of plasticisers both of different and identical composition.
- the term “different composition” refers to both the type of plasticiser and proportion thereof in the mixture. It may contain, in the starting state prior to lamination, at least 22 % by weight, such as 22.0 - 45.0 % by weight, preferably 25.0 - 32.0 % by weight and in particular 26.0 - 30.0 % by weight plasticiser.
- the thickness of the at least one film containing a polyvinyl acetal in the starting state is 450 - 2500 pm, preferably 600 - 1000 pm, preferably 700 - 900 pm.
- a plurality of films B may be used in the invention either being stacked on each other or separated by the ethylene vinyl acetal film.
- the laminated glass can be produced by inserting and laminating the interlayer film of the present invention as well as the at least one film containing a polyvinyl acetal between two or more sheets of glass made of inorganic glass or organic glass.
- a conventionally known organic glass such as polymethyl methacrylate or polycarbonate can be used in addition to an inorganic glass such as float glass, reinforced glass, netted glass, or heat ray absorbing plate glass.
- the thickness of the glass it is preferably 1 to 10mm, more preferably 2 to 6mm.
- Laminating methods for obtaining the laminated glass described above are known in the art and examples thereof include a method using a vacuum laminator apparatus, a method using a vacuum bag, a method using a vacuum ring, and a method using a nip roll. Further, after temporary bonding, the method of throwing into the autoclaving step can also be performed additionally.
- a nip roll for example, a method in which a first temporary adhesion is performed at a temperature lower than or close to the Tg.
- a method in which the mixture is heated to 30 to 70 °C by an infrared heater or the like, then degassed by a roll, and further heated to 50 to 120 °C, and then crimped by a roll to be bonded or temporarily bonded.
- the autoclaving step which is performed after the temporary bonding, is carried out for about 2 hours at a temperature of 120 to 145 °C, for example, under a pressure of about 1 to 1 5MPa, although depending on the thickness and configuration of the module and the laminated glass.
- Yet another aspect of the present invention concerns the use of the interlayer film as hot melt for fabrics, wood, metals, ceramics or polymer fibres as well as composites comprising at least two fabric layers combined by at least one interlayer film according to the present invention, such as for examples personal protection gear like helmets and vests.
- the ethylene vinyl acetal thus obtained has a content of ethylene units of 44 mol% and an acetalization degree of 31 mol%.
- the interlayer is produced from the resin obtained as described above by film extrusion using a Leistritz co-rotating double-screw extruder with a screw length of 592 mm and a length/ diameter (L/D) ratio of 32.
- the melt temperature during extrusion is between 180 and 240 °C.
- the film is extruded through a flat slit die with a slit width of 300 mm and cooled down by chill rolls, that have a surface temperature of 20 °C.
- the obtained film has a thickness of 50 pm.
- the films were compression-moulded with a hot press at 200 °C, a pressure of 50 bar and a residence time of 5 min.
- the obtained samples have a thickness of 0.7 mm and were pre-derided for 24 h in a vacuum oven at 50 °C.
- the complex viscosity was measured in the linear range of deformation at 190 °C using a commercially available rheometer in plate/plate mode (Anton Paar MCR 302, plate dimeter 25 mm).
- the applied frequency range was 0.1 - 100 rad/s.
- the storage modulus was measured using the same rheometer as for the viscosity measurements.
- the used geometry has a diameter of 8 mm.
- the frequency was set to 1 Hz and the heating rate to 2 K/min.
- the measurements were performed in the linear range of deformation.
- the obtained film has a Haze value (acc. ASTM 1300) ⁇ 1 and a yellowness db ⁇ 1 .
- Mowital® vinyl acetal resin B60T obtained from Kuraray Europe GmbH, which contains acetal units prepared only with n-butyraldehyd, is used for film extrusion as described above. No plasticizer was added. Comparative Example 3
- Trosifol® Extra Stiff film was obtained from Kuraray Europe GmbH.
- the commercially available product contains PVB and a plasticizer content of 17 %.
- Figure 1 shows the complex viscosity as a function of frequency at a typical extrusion temperature of 190 °C.
- Comparative Example 2 shows a significant higher viscosity compared to the inventive Example 1 .
- a high viscosity can cause the above mentioned problems.
- Figure 2 shows the shear storage modulus G’ as a function of temperature T for the comparative Examples 2 & 3 and the inventive Example 1 .
- the commercially available Trosifol® Extra Stiff shows a strong drop of the modulus already around 40 °C (Example 3). This is caused by the high plasticizer amount of 17 % and is obstructive for a functionalisation step at higher temperatures (> 50 °C).
- the commercial available vinyl acetal resin Mowital® B60T indicates superior high modulus values until approx. 80 °C.
- the high viscosity at extrusion temperature is of disadvantage.
- the inventive Example 1 combines the advantages of both comparative Examples - a high modulus over the temperature range between 20 and 100 °C and a low viscosity at extrusion temperature. This enables extrusion with superior optical properties and the processed film can be functionalized easily.
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Joining Of Glass To Other Materials (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
L'invention concerne des films intercouches de faible épaisseur comprenant un acétal de vinyle-éthylène et éventuellement au moins un plastifiant.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP20198635.3A EP3974177A1 (fr) | 2020-09-28 | 2020-09-28 | Films minces comprenant des acétals de vinyle d'éthylène |
PCT/EP2021/075874 WO2022063747A1 (fr) | 2020-09-28 | 2021-09-21 | Films minces comprenant des acétals de vinyle-éthylène |
Publications (1)
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EP4204225A1 true EP4204225A1 (fr) | 2023-07-05 |
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EP20198635.3A Withdrawn EP3974177A1 (fr) | 2020-09-28 | 2020-09-28 | Films minces comprenant des acétals de vinyle d'éthylène |
EP21777549.3A Pending EP4204225A1 (fr) | 2020-09-28 | 2021-09-21 | Films minces comprenant des acétals de vinyle-éthylène |
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EP20198635.3A Withdrawn EP3974177A1 (fr) | 2020-09-28 | 2020-09-28 | Films minces comprenant des acétals de vinyle d'éthylène |
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WO (1) | WO2022063747A1 (fr) |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7008618B1 (en) | 2002-11-08 | 2006-03-07 | Nalco Company | Water soluble monomers and polymers for protecting substrates from ultraviolet light |
DE102004007382A1 (de) | 2004-02-11 | 2005-09-01 | Basf Ag | Schwarze Perylenpigmente |
US7964245B2 (en) | 2008-06-27 | 2011-06-21 | Hallstar Innovations Corp. | UV-absorbing and photostabilizing polymers |
US10179442B2 (en) * | 2013-01-11 | 2019-01-15 | Kuraray Europe Gmbh | Fluorescent displays containing an interlayer film of polyvinylacetal which comprises plasticizers |
JP6704688B2 (ja) | 2014-07-11 | 2020-06-03 | 株式会社クラレ | 樹脂組成物及び多層構造体 |
EP3095601B1 (fr) * | 2015-05-22 | 2023-07-05 | Kuraray Europe GmbH | Verre feuilleté résistant à la pénétration, fabriqué avec des couches de film intercouches présentant une adhérence réduite et une faible teneur en plastifiant |
CN106609399A (zh) | 2015-10-21 | 2017-05-03 | 东丽纤维研究所(中国)有限公司 | 一种柔软纤维及其织物 |
EP3272792A1 (fr) * | 2016-07-19 | 2018-01-24 | Kuraray Europe GmbH | Films minces comprenant du co-acétal polyvinyl exempt de plastifiant |
CN110944835A (zh) | 2017-08-25 | 2020-03-31 | 可乐丽欧洲有限责任公司 | 包含具有着色框的夹层膜层的层压玻璃 |
KR20200102468A (ko) * | 2017-12-22 | 2020-08-31 | 쿠라라이 유럽 게엠베하 | 임베딩된 투명 영역들을 갖는 엄폐 영역들을 갖는 라미네이팅된 유리 |
EP3702150A1 (fr) * | 2019-02-26 | 2020-09-02 | Kuraray Europe GmbH | Verre stratifié comprenant des couches de film intermédiaires avec une région colorée |
-
2020
- 2020-09-28 EP EP20198635.3A patent/EP3974177A1/fr not_active Withdrawn
-
2021
- 2021-09-21 WO PCT/EP2021/075874 patent/WO2022063747A1/fr unknown
- 2021-09-21 EP EP21777549.3A patent/EP4204225A1/fr active Pending
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