EP2396357A1 - 2k-polyurethan-lack für trägerfolien - Google Patents
2k-polyurethan-lack für trägerfolienInfo
- Publication number
- EP2396357A1 EP2396357A1 EP10706146A EP10706146A EP2396357A1 EP 2396357 A1 EP2396357 A1 EP 2396357A1 EP 10706146 A EP10706146 A EP 10706146A EP 10706146 A EP10706146 A EP 10706146A EP 2396357 A1 EP2396357 A1 EP 2396357A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- component
- aqueous
- hydroxy
- polyurethane paint
- acid
- 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.)
- Withdrawn
Links
- 239000003973 paint Substances 0.000 title claims abstract description 26
- 239000004814 polyurethane Substances 0.000 title claims description 28
- 229920002635 polyurethane Polymers 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 239000005056 polyisocyanate Substances 0.000 claims description 38
- 229920001228 polyisocyanate Polymers 0.000 claims description 38
- 239000004417 polycarbonate Substances 0.000 claims description 30
- 229920000515 polycarbonate Polymers 0.000 claims description 30
- 229920000728 polyester Polymers 0.000 claims description 30
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 24
- 150000002009 diols Chemical class 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 239000006185 dispersion Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 14
- 229920003009 polyurethane dispersion Polymers 0.000 claims description 14
- 238000004132 cross linking Methods 0.000 claims description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- 229920005862 polyol Polymers 0.000 claims description 9
- 150000003077 polyols Chemical class 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000004971 Cross linker Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000011527 polyurethane coating Substances 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000008040 ionic compounds Chemical class 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 230000000295 complement effect Effects 0.000 claims description 2
- 238000005227 gel permeation chromatography Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 20
- 239000002991 molded plastic Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 36
- 238000000576 coating method Methods 0.000 description 31
- 239000011248 coating agent Substances 0.000 description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- -1 polyethylene Polymers 0.000 description 18
- 239000004922 lacquer Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- ZAXXZBQODQDCOW-UHFFFAOYSA-N 1-methoxypropyl acetate Chemical compound CCC(OC)OC(C)=O ZAXXZBQODQDCOW-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000010422 painting Methods 0.000 description 6
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
- 229940117969 neopentyl glycol Drugs 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000004848 polyfunctional curative Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229920001169 thermoplastic Polymers 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 229920001707 polybutylene terephthalate Polymers 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 4
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229960002887 deanol Drugs 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- 239000012972 dimethylethanolamine Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 238000010137 moulding (plastic) Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
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- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
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- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
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- 229920005749 polyurethane resin Polymers 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
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- 230000003678 scratch resistant effect Effects 0.000 description 2
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- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
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- AWSFICBXMUKWSK-UHFFFAOYSA-N ytterbium(3+) Chemical compound [Yb+3] AWSFICBXMUKWSK-UHFFFAOYSA-N 0.000 description 2
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- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
- C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
- C08G18/4216—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from mixtures or combinations of aromatic dicarboxylic acids and aliphatic dicarboxylic acids and dialcohols
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
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- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D169/00—Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates
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- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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- C09D175/06—Polyurethanes from polyesters
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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- C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
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- C08J2475/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2475/04—Polyurethanes
Definitions
- the invention relates to a two-component (2K) -polyurethane paint for a carrier film, a process for its preparation and their use for the equipment of plastic moldings.
- thermoplastics are relatively sensitive to their mechanical and chemical resistance.
- the direct coloring by coloring the substrate is limited in terms of the colors and effects to be achieved.
- injection molding may cause visible surface defects, such as flow lines, that are unacceptable for vision applications.
- foamed components frequently have surface defects and / or pores, which considerably complicate error-free painting. Especially after any grinding operations, the affected parts must be manually filled prior to painting.
- Composite elements of lacquer layer and plastic component are usually produced by subsequent painting in the spraying or dipping process of the previously foamed or produced by injection molding component. In automotive engineering in particular, this is the preferred procedure for producing large-area components or those with complex geometry.
- This subsequent application of the lacquer layer requires a large number of separate working steps, some of which have to be carried out manually and can not be automated.
- certain partial surfaces of the component can be coated only very expensive.
- overspray When painting three-dimensional body is also to be expected with a significant loss of material of the paint, the so-called overspray.
- the error rate in the painting of three-dimensional parts is significantly higher than in the technically easier coating of two-dimensional films.
- plastic films are coated over a large area by means of common coating methods such as doctoring, rolling or spraying and this coating by physical drying or partial curing dries almost tack-free. These films can then be deformed at elevated temperatures and then glued, back-injected or backfoamed.
- This concept offers a great deal of potential for the production of, for example, components by plastic processors, whereby the more complex painting step of three-dimensional components can be replaced by the simpler coating of a flat substrate.
- EP-A 1 647 399 describes composite moldings consisting of a carrier film and soft-touch lacquer applied to this film.
- This carrier foil is used for injection-molding or back-pressing with thermoplastics without damaging the soft-touch lacquer layer. For example, there are no shiny spots and no cracks in the paint layer.
- the polyol component contained in the paint formulation contains, in addition to building blocks which react chemically with the polyisocyanate crosslinker, elastifying, hydroxyl- and / or amine-group-free polyurethanes. These dry only physically and do not crosslink by a chemical reaction on the substrate. Therefore, such coatings do not achieve the high level of scratch and chemical resistance of fully chemically reacting paints.
- Block resistance means the bonding effect that occurs when joining two coated surfaces under loads such as temperature or pressure.
- the coating may be prone to dust due to the low Tg.
- a degree of drying / blocking resistance of the coating is achieved before radiation curing, in which after a load of 500 g / cm 2 for 60 s at 10 0 C still stampings of a filter paper are visible.
- the stresses on a coating in a film roll are usually higher in terms of pressure and temperature.
- the object of the present invention was therefore to provide a novel aqueous polyurethane lacquer for coating a carrier film, which has a high level of scratch and chemical resistance with simultaneously high degrees of stretching.
- the coated carrier film should be able to be wound on rolls without the coating showing cracks. It should also be given a high blocking resistance, i. that the carrier film should be able to unwind easily without sticking from the roll.
- thermoplastic carrier films solve this problem.
- the present invention thus provides an aqueous 2-component polyurethane lacquer containing
- the crosslinking ratio is preferably 1.2: 1 to 1.4: 1.
- the 2K polyurethane paint may contain other auxiliaries and additives C).
- the average functionality of the polyisocyanates B) is 2.5 to 3.3, preferably 2.8 to 3.0.
- the preparation of the polyester polyurethane dispersion A) is carried out by polyaddition of the components al) to a5) and subsequent neutralization of the carboxylic acid and dispersion in water.
- the components a5) are preferably low molecular weight compounds of molecular weight Mn 62 to 400 g / mol which have a total of two or more, preferably three hydroxyl and / or amino groups.
- Preferred polyester polyurethane dispersions A) contain 20 to 50 wt .-%, preferably 30 to 40 wt .-% component al), 20 to 50 wt .-%, preferably 30 to 40 wt .-% component a2), 2 to 6 Wt .-%, preferably 3 to 5 wt .-% of component a3), 10 to 30 wt .-%, preferably 15 to 25 wt .-% of component a4), 0.5 to 10 wt .-%, preferably 2 to 5 wt .-% component a5), wherein the percentages al) to a5) to 100 wt .-% complement.
- the acid groups incorporated to stabilize the dispersion via component a3) are present as salt groups at from 40 to 120%, preferably from 50 to 80%.
- the acid numbers of the hydroxy-functional polyester-polyurethane dispersions according to the invention incorporated in component a3) are 5.0 to 14.5 mg KOH / g substance, preferably 8.0 to 11 mg KOH / g substance, in each case based on the aqueous dispersion of polyester polyurethane.
- the average molecular weight M w of the polyester polyurethane dispersion A is from 3,000 to 30,000 g / mol, preferably from 5,000 to 15,000 g / mol, more preferably from 6,000 to 10,000 g / mol and thus substantially lower than, for example, polyurethane dispersions according to the prior art.
- the polyester al) contained in the polyester polyurethane dispersion A) can be prepared by processes known per se with elimination of water at temperatures of 100 to 260 0 C, optionally with concomitant use of conventional esterification catalysts, preferably according to the principle of a melt or azeotropic condensation.
- Preferred production process for the polyester al) is a melt condensation in vacuo or using an inert gas. It is also possible here to use mixtures of different polyesters and also mixtures of polyesters with different functionalities, the average functionality of the polyesters a1) being between 1.8 and 2.5, preferably 1.9 and 2.1 and particularly preferably 2.0 lies.
- the polyesters al) have mathematically determined theoretical molecular weights of 500 to 3000 g / mol, preferably from 500 to 1000 g / mol.
- the theoretical molecular weight of the polyester is determined according to the formula: mass of the batch [g] / (mol COOH + mol OH) - VaI COOH.
- Preferably used polyesters al) are reaction products of
- al m 0 to 10% by weight of at least one alcohol having more than 2 hydroxyl groups
- al lv 0 to 10 wt .-% of other hydroxy- and / or carboxy-functional components and / or caprolactone.
- Suitable polyester raw materials al are e.g. Phthalic anhydride, isophthalic acid, terephthalic acid, adipic acid, sebacic acid, suberic acid, succinic acid, maleic anhydride, fumaric acid, dimer fatty acids, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, cyclohexanedicarboxylic acid and / or trimellitic anhydride or mixtures thereof.
- Phthalic anhydride isophthalic acid, terephthalic acid, adipic acid, sebacic acid, suberic acid, succinic acid, maleic anhydride, fumaric acid, dimer fatty acids, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, cyclohexanedicarboxylic acid and / or trimellitic anhydride or mixtures thereof.
- Preferred components al,) are adipic acid, phthalic anhydride, tetrahydrophthalic anhydride, isophthalic acid or glutaric acid, particular preference is given to adipic acid and hexahydrophthalic acid or phthalic acid and their anhydrides.
- Suitable polyester raw materials al u are, for example, 1,2-ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, 1,2-propylene glycol, dipropylene glycol, tripropylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,6 Hexanediol, neopentylglycol, 1,4-cyclohexanedimethanol, 1,4-cyclohexanediol, butenediol, butynediol, hydrogenated bisphenols, trimethylpentanediol, 1,8-octanediol and / or tricyclodecanedimethanol and mixtures thereof.
- Preferred components al u are 1, 4-butanediol, neopentyl glycol, 1, 2-propylene glycol, ethylene glycol, diethylene glycol or 1,6-hexanediol.
- Preferred components al n are neopentyl glycol, butanediol and hexanediol.
- Suitable polyester raw materials a I 111 are, for example, trimethylolpropane, ethoxylated trimethylolpropane, propoxylated trimethylolpropane, propoxylated glycerol, ethoxylated glycerol, glycerol, pentaerythritol, castor oil and mixtures thereof.
- Preferred component a I 111 ) is trimethylolpropane.
- Suitable optionally used polyester raw materials as IV are, for example, C 8 -C 22 -fatty acids such as 2-ethylhexanoic acid, stearic acid, hydrogenated fatty acids, benzoic acid, monofunctional alcohols such as butylglycol, butyldiglycol, cyclohexanol, other monofunctional alcohols such as polyethylene oxides, polypropylene oxides, polyethylene / propylene oxide mixture - or block copolymers and mixtures thereof.
- C 8 -C 22 -fatty acids such as 2-ethylhexanoic acid, stearic acid, hydrogenated fatty acids, benzoic acid, monofunctional alcohols such as butylglycol, butyldiglycol, cyclohexanol, other monofunctional alcohols such as polyethylene oxides, polypropylene oxides, polyethylene / propylene oxide mixture - or block copolymers and mixtures thereof.
- the structural component a2) are linear, hydroxy-functional polycarbonates.
- Suitable polycarbonates a2) are those which are e.g. by reaction of carbonic acid derivatives, e.g. Diphenyl carbonate, dimethyl carbonate or phosgene with polyols, preferably diols are available. As such diols come e.g.
- Ethylene glycol 1,2- and 1,3-propanediol, 1,3- and 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, neopentyl glycol, 1,4-bis-hydroxymethylcyclohexane, 2-methyl-1, 3-propanediol, 2,2,4-Trimethylpentandiol-l, 3, dipropylene glycol, polypropylene glycols, dibutylene glycol, polybutylene glycols, bisphenol A, tetrabromobisphenol A but also lactone-modified diols in question.
- the diol component contains from 40 to 100% by weight of hexanediol, preferably 1,6-hexanediol and / or hexanediol derivatives, preferably those having, in addition to terminal OH groups, ether or ester groups, e.g. Products obtained by reacting 1 mole of hexanediol with at least 1 mole, preferably 1 to 2 moles of caprolactone or by etherification of hexanediol with itself to di- or Trihexylenglykol. Polyether-polycarbonate diols can also be used. The hydroxyl polycarbonates should be substantially linear.
- polyfunctional components especially low molecular weight polyols.
- polyfunctional components especially low molecular weight polyols.
- glycerol, trimethylolpropane, hexanetriol-1,2,6, butanetriol-1,2,4, trimethylolpropane, pentaerythritol, quinitol, mannitol, sorbitol, methyl glycoside or 1,3,4,6-dianhydrohexitols are suitable for this purpose.
- the polycarbonate polyols are preferably prepared by the preparation process described in EP-A 1 404 740 (pages 6-8, examples 1-6) and EP-A 1 477 508 (page 5, example 3).
- Particularly preferred polycarbonate polyols a2) are those which contain at least 25% by weight of 1,4-butanediol as the synthesis component and have an average hydroxyl functionality of from 1.6 to 4, preferably from 1.8 to 3 and particularly preferably from 1.9 to 2, 3 and a number average Molecular weight of 240 to 8000 g / mol, preferably from 500 to 3000 g / mol, particularly preferably from 750 to 2500 g / mol.
- the diol component preferably contains from 45 to 100% by weight of 1,4-butanediol, and from 1 to 55% by weight of 1,6-hexanediol, particularly preferably from 60 to 100% by weight of 1,4-butanediol and from 1 to 40% by weight .-% 1,6-hexanediol.
- the hydroxylpolycarbonates are preferably linear, but may optionally be branched by the incorporation of polyfunctional components, in particular low molecular weight polyols.
- Particularly preferred components a2) are based on mixtures of 1,4-butanediol and 1,6-hexanediol and have an average hydroxyl functionality of 1.9 to 2.05.
- Component a3) contains at least one ionic or potentially ionic compound having at least one acid group and at least one isocyanate-reactive group.
- Suitable acid groups are e.g. Carboxyl and sulphonic acid groups.
- Suitable isocyanate-reactive groups are e.g. Hydroxyl and / or amino groups.
- Component a3) is preferably at least one, preferably one or two, hydroxyl-containing carboxylic acid.
- Dimethylolpropionic acid, dimethylolbutyric acid and / or hydroxypivalic acid are particularly preferred as component a3), very particular preference is given to using dimethylolpropionic acid.
- acids are, for example, other 2,2-bis (hydroxymethyl) alkanecarboxylic acid, e.g. Dimethylolacetic acid or 2,2-dimethylolpentanoic acid, dihydroxysuccinic acid, Michael addition products of acrylic acid to amines such as e.g. Isophoronediamine or hexamethylenediamine, or mixtures of such acids and / or dimethylolpropionic acid and / or hydroxypivalic acid. It is likewise possible to use sulfonic acid diols optionally having ether groups of the type described in US Pat. No. 4,108,814 or else 2-aminoethyl-aminoethanesulphonic acid.
- sulfonic acid diols optionally having ether groups of the type described in US Pat. No. 4,108,814 or else 2-aminoethyl-aminoethanesulphonic acid.
- the free acid groups represent "potentially ionic” groups, while the salt-like groups, carboxylate or sulfonate groups obtained by neutralization with neutralizing agents are “ionic" groups.
- Suitable polyisocyanates of component a4) are the aromatic, araliphatic, aliphatic or cycloaliphatic polyisocyanates of an NCO functionality of preferably> 2 which are known to the person skilled in the art and which also include iminooxadiazinedione, isocyanurate, uretdione, urethane, allophanate, biuret , Urea, oxadiazinetrione, oxazolidinone, acylurea and / or may have carbodiimide structures. These can be used individually or in any mixtures with each other.
- Suitable polyisocyanates a4) are butylene diisocyanate, hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), 2,2,4- and / or 2,4,4-Trirnethylhexamethylendiisocyanat, the isomeric bis (4,4'-isocyanatocyclohexyl) methanes or mixtures thereof any isomer content, isocyanatomethyl-l, 8-octane diisocyanate, 1,4-cyclohexylene diisocyanate, 1,4-phenylene diisocyanate, 2,4- and / or 2,6-toluene diisocyanate, 1,3- and 1,4-bis (2-methyl) isocyanato-prop-2-yl) -benzene (TMXDI), 1,3-bis (isocyanato-methyl) -benzene (XDI), 1,5-naphthylene-diis
- non-modified polyisocyanate having more than 2 NCO groups per molecule see e.g. 4-Isocyanatomethyl-l, 8-octane diisocyanate (nonane triisocyanate) called.
- polyisocyanates or polyisocyanate mixtures of the abovementioned type with exclusively aliphatically and / or cycloaliphatically bonded isocyanate groups.
- Particularly preferred are hexamethylene diisocyanate, isophorone diisocyanate, the isomeric bis (4,4'-isocyanatocyclohexyl) methanes and mixtures thereof.
- the process for the preparation of the aqueous polyester-polyurethane dispersion can be carried out in one or more stages in homogeneous or in multistage reaction, partly in disperse phase. After complete or partial polyaddition from al) to a4), a dispersing, emulsifying or dissolving step takes place. This is followed, if appropriate, by a further polyaddition or modification in disperse phase.
- Suitable neutralizing agents which may already be present on reaction of components a1) to a4) are e.g. Triethylamine, N-methylmorpholine, dimethylisopropylamine, ethyldiisopropylamine, dimethylcyclohexylamine, triethanolamine, dimethylethanolamine, ammonia, potassium hydroxide and / or sodium hydroxide.
- the hydroxy-functional polyester-polyurethane dispersions A) generally contain from 0 to 10% by weight, preferably from 0 to 3% by weight, of organic solvents.
- the optionally carried out by distillation removal of excess amounts of solvent can be carried out, for example, under reduced pressure at, for example, 20 to 80 0 C during or after dispersing in / with distilled water.
- the solids content of the polyester polyurethane dispersion A) is 40 to 60 wt .-%, preferably 50 to 57 wt .-%.
- the dispersions A) have particle diameters determined e.g. by LKS measurements, from 80 to 500 nm, preferably from 100 to 200 nm.
- the hydroxy-functional, urethane-containing polyester dispersions A) are combined in combination with, optionally hydrophilized, polyisocyanates B) with free isocyanate groups to form the aqueous 2-component coating compositions according to the invention.
- the coating agent has a limited pot life of up to 24 hours.
- the coatings produced therefrom are curable at room temperature to 120 0 C.
- polyisocyanates are used with free isocyanate groups.
- Suitable polyisocyanates are, for example, based on isophorone diisocyanate, hexamethylene diisocyanate, 1,4-diisocyanatocyclohexane, bis (4-isocyanatocyclohexane) -methane or 1,3-diisocyanocatobenzene or based on lacquer polyisocyanates such as allophanate, uretdione, biuret or isocyanurate polyisocyanates of 1,6-diisocyanatohexane, isophorone diisocyanate or bis (4-iso-cyanatocyclohexan) methane or urethane containing lacquer polyisocyanates based on 2,4- and / or 2,6-diisocyanatotoluene or isophorone diisocyanate on the one hand and low molecular weight Polyhydroxyl compounds
- Preferred as components B) are low-viscosity, hydrophobic or hydrophilicized polyisocyanates having free isocyanate groups based on aliphatic, cycloaliphatic, araliphatic and / or aromatic isocyanates, particular preference being given to aliphatic or cycloaliphatic isocyanates.
- These polyisocyanates generally have a viscosity of from 10 to 3500 mPas at 23 ° C. If necessary, the polyisocyanates may be used in admixture with small amounts of inert solvents to lower the viscosity to a value within the stated range.
- Triisocyanatononan can be used alone or in mixtures as a crosslinking component.
- Water-soluble or dispersible polyisocyanates are obtainable, for example, by modification with carboxylate, sulfonate and / or polyethylene oxide groups and / or polyethylene oxide / polypropylene oxide groups.
- hydrophilization of the polyisocyanates B it is preferable to react the polyisocyanates with substoichiometric amounts of monohydric, hydrophilic polyether alcohols. The preparation of such hydrophilicized polyisocyanates is described, for example, in EP-A 0 540 985.
- polyisocyanates containing allophanate groups described in EP-A 0 959 087 which are prepared by reacting low-monomer polyisocyanates with polyethylene oxide polyether alcohols under allophanatization conditions.
- the water-dispersible polyisocyanate mixtures based on triisocyanatononane described in DE-A 100 078 21 are also suitable, as are polyisocyanates hydrophilized with ionic groups (sulfonate, phosphonate groups), as described, for example, in DE-A 100 24 624.
- hydrophilization by addition of commercially available emulsifiers.
- component B mixtures which contain flexibilized polyisocyanate components B) which are readily obtained by prepolymerization of the abovementioned polyisocyanate components with preferably di- to trifunctional polyol components, particularly preferably polyol components as already mentioned under structural components a1).
- hardener components are polyisocyanates modified with sulfonate groups, as described, for example, in US Pat. in DE-A 100 24 624, are used.
- component B as so-called blocked polyisocyanates.
- Blocking agents for these polyisocyanates are, for example, monohydric alcohols such as
- dispersions A) are applied alone to substrates, preferably films, then clear, very well-running layers without defects or craters are obtained and very high layer thicknesses of more than 100 ⁇ m are possible.
- the dispersions A) show no pronounced physical drying, that is, the layers remain more or less sticky or grippy. Cured, tack-free and hard layers are obtained only by combination with at least one crosslinker polyisocyanate B) and curing.
- the aqueous 2-component polyurethane coating according to the invention applied as a coating on top of the carrier films may, in addition to components A) and B), optionally contain the customary auxiliaries and additives C), such as organic and / or inorganic pigments or metallic pigments based on aluminum fiocken, Fillers such as carbon black, silica, talc, kaolin, glass powder or in the form of fibers and mixtures of these and / or other common materials for the production of paints, coatings and adhesives.
- the customary auxiliaries and additives C) such as organic and / or inorganic pigments or metallic pigments based on aluminum fiocken, Fillers such as carbon black, silica, talc, kaolin, glass powder or in the form of fibers and mixtures of these and / or other common materials for the production of paints, coatings and adhesives.
- auxiliaries customary in the paint and adhesives industry in the preparation of the polyester dispersion A such as, for example, surface-active substances, emulsifiers, stabilizers, anti-settling agents, UV stabilizers, catalysts for the crosslinking reaction, defoamers, antioxidants, anti-skinning agents, leveling agents, thickeners and / or bactericides.
- the aqueous two-component polyurethane coating according to the invention contains a silicone-containing silicone additive, with which a particularly smooth surface is obtained.
- the two-component polyurethane lacquer according to the invention is basically suitable for the coating, lacquering, bonding, treatment and sealing of a wide variety of substrates, in particular metals, wood, ceramics, stone, concrete, bitumen, hardboard, glass, porcelain, plastics, leather and / or textileskind suitable.
- a preferred application is the coating of plastic.
- Particularly preferred is the coating of polycarbonate.
- aqueous two-component polyurethane lacquers according to the invention can be applied to the substrate to be coated by methods known per se, such as spraying, flooding, casting, dipping, rolling, brushing.
- the 2K aqueous polyurethane paints may also be used as part of a multi-layer paint system consisting of e.g. from primer and / or filler and / or basecoat and / or topcoat. Wet-in-wet coating processes are also possible in which at least two layers are applied one after the other, if necessary pre-dried and then baked together.
- the lacquers may also contain one or more other aqueous dispersions, e.g. polyester-based, polyurethane-based, polyurethane-polyacrylate-based, polyacrylate-based, polyether-based, polyester-polyacrylate-based, alkyd-resin-based, polymer-based, on
- aqueous two-component polyurethane lacquers according to the invention used as a coating for the production of the carrier film are characterized by a very good processability.
- the resulting coatings have excellent film appearance and flow, very low crater susceptibility, good resistance properties, a balanced hardness / elasticity level and very good storage stability.
- the carrier films have excellent blocking resistance, ie the carrier films can be unrolled from the roll without problems after being rolled up.
- the layer thicknesses can be between 2 microns and 100 microns, preferably between 5 and 75 microns, more preferably between 5 and 50 microns.
- the carrier films For the production of the carrier films, conventional plastic films, e.g. from PET, polycarbonate, PMMA, polysulfone, etc. are used. Optionally, the films may be pretreated by methods such as corona treatment, etc.
- the carrier films preferably have thicknesses between 2 and 2,000 micrometers. Preferably, carrier films of polycarbonate and polycarbonate blends are used.
- the carrier films may also be so-called composite films made of a plurality of plastic layers.
- Suitable carrier films are in principle all known per se or commercially available polycarbonates.
- the polycarbonates suitable as a carrier film preferably have a molecular weight in the range from 10,000 to 60,000 g / mol. They are e.g. according to the method of DE-B-I 300 266 by interfacial polycondensation or according to the method of DE-A-I 495 730 by reaction of diphenyl carbonate with bisphenols available.
- Preferred bisphenol is 2,2-di (4-hydroxyphenyl) propane, generally - as hereinafter referred to as bisphenol A.
- bisphenol A instead of bisphenol A, it is also possible to use other aromatic dihydroxy compounds, in particular 2,2-di (4-hydroxyphenyl) pentane, 1,6-dihydroxynaphthalene, 4,4'-dihydroxydiphenylsulfane, 4,4'-dihydroxydiphenyl ether, 4,4 'Dihydroxydiphenylsulfon, 4,4'-dihydroxydiphenylmethane, l, l-di (4-hydroxyphenyl) ethane, 4,4'dihydroxydiphenyl or dihydroxydiphenyl cycloalkanes, preferably Dihydroxydiphenylcyclohexane or Dihydroxycyclopentane and mixtures of the aforementioned dihydroxy compounds.
- aromatic dihydroxy compounds in particular 2,2-di (4-hydroxyphenyl) pentane, 1,6-dihydroxynaphthalene, 4,4'-dihydroxydiphenylsulfane, 4,4'-dihydroxydiphenyl
- support film polycarbonates are those which contain units derived from Resorcinol- or Alkylresorcinolestern, as described for example in WO 00/15718 or WO 00/26274; These polycarbonates are marketed, for example, General Electric Company under the trademark Sollx ®. In addition to these carrier films and blends or mixtures of plastics can be used. Blends of polycarbonate and polyesters, for example polybutylene terephthalate or polyethylene terephthalate, and polyesters of cyclohexanedicarboxylic acid and cyclohexanedimethanol have proven particularly advantageous. Such products are sold under the names Bayfol ® from Bayer MaterialScience AG or Xylex ® by General Electric Company.
- copolycarbonates according to US Pat. No. 3,737,409; Of particular interest are copolycarbonates based on bisphenol A and di- (3,5-dimethyl-dihydroxyphenyl) sulfone, which are distinguished by a high heat resistance. It is also possible to use mixtures of different polycarbonates.
- Impact-resistant PMMA is a polymethyl methacrylate which is impact-modified by suitable additives and is preferably used. Suitable impact-modified PMMA are described, for example, by M. Stickler, T.Rhein in Ullmann's Encyclopedia of Industrial Chemistry Vol. A 21, pages 473-486, VCH Publishers Weinheim, 1992, and H. Domininghaus, Die Kunststoffe und hi compassion, VDI-Verlag Dusseldorf, 1992.
- the carrier film For the production of the carrier film, all known methods, for example by adapter or coextrusion or stacking of layers in question.
- the carrier film can also be cast from solution.
- the surface of the carrier film can be glossy, structured or matted.
- thermoplastic polymers such as polyolefins, e.g. Polyethylene or polypropylene, polyester, e.g. Polybutylene terephthalate (PBT) and polyethylene terephthalate (PET), polycycloolefins, poly (meth) acrylates, polyamides,
- Polycarbonates polyurethanes, polyacetals, e.g. Polyoxymethylene (POM), polystyrenes,
- Polyphenylene ethers Polysulfones, polyethersulfones, polyether ketones, styrene (co) polymers or mixtures of the aforementioned polymers.
- Particularly suitable polycarbonates are bisphenol A and TMC bisphenol polycarbonates.
- Preferred polymer blends include polycarbonate and polybutylene terephthalate or polycarbonate and ABS polymer.
- Formations also vertical formations or depressions, such as mobile phone keyboards, getting produced.
- the good surface properties associated with the carrier films are therefore also accessible in the case of composite moldings with sophisticated geometry.
- the carrier films of the invention are used in telecommunications equipment, in vehicle, ship and aircraft.
- the present invention also relates to the use of the carrier film according to the invention for the equipment of plastic moldings, preferably screen housing.
- BYK ® 348 wetting agent (BYK-Chemie, Wesel, DE)
- BYK ® 337 surface additive (BYK-Chemie, Wesel, DE)
- Tinuvin ® 292 HALS amine (Ciba GmbH, Lampertheim, DE)
- Tinuvin ® 384-2 UV absorber (Ciba GmbH, Lampertheim, DE)
- Bayhydur® ® XP 2655 Hydrophilic polyisocyanate (Bayer MaterialScience AG, DE); average functionality 3.1.
- the solids contents were determined according to DIN-EN ISO 3251.
- NCO contents were determined volumetrically in accordance with DIN-EN ISO 11909, unless expressly stated otherwise.
- a 151-reaction vessel with stirrer, heater and water with a condenser 1281 g of phthalic anhydride, 5058 g of adipic acid, 6387 g of 1,6-hexanediol and 675 g of neopentyl glycol were weighed and heated under nitrogen in one hour at 140 0 C. In a further 9 hours was heated to 220 ° C and condensed at this temperature until an acid number less than 3 was reached.
- the polyesterpolyol thus obtained had a viscosity (determined as the flow time of an 80% strength solution of the polyester in methoxypropyl acetate in the DIN 4 cup at 23 ° C.) of 54 seconds and an OH number of 160 mg KOH / g.
- the reaction mixture was cooled to 130 0 C and the pressure was lowered to 10 mbar. This was followed by an increase in the oil bath temperature of 13O 0 C to 180 0 C within 2 h, the distillation head temperature 60 0 C was not exceeded. After reaching 180 0 C, this temperature was maintained for 6 h.
- reaction mixture was cooled to 130 0 C and the pressure was lowered to 10 mbar. This was followed by an increase in the oil bath temperature of 130 0 C to 180 0 C within 2 h, the distillation head temperature 60 0 C was not exceeded. After reaching 180 0 C, this temperature was maintained for 6 h. The reaction mixture was cooled to room temperature and the characteristics of the product determined.
- the reaction mixture was cooled to 130 0 C and the pressure was lowered to 10 mbar. This was followed by an increase in the oil bath temperature of 130 0 C to 180 0 C within 2 h, the distillation head temperature 60 0 C was not exceeded. After reaching 180 0 C, this temperature was maintained for 6 h. Subsequently, the reaction mixture was cooled to 130 0 C and the pressure was lowered to 10 mbar. This was followed by an increase in the oil bath temperature of 130 0 C to 180 0 C within 2 h, the distillation head temperature 60 0 C was not exceeded. After reaching 180 0 C, this temperature was maintained for 6 h. Thereafter, the reaction mixture was cooled to room temperature and the characteristics of the product determined.
- Polycarbonate diol from Example 2 90 g of trimethylolpropane, 120 g of dimethylolpropionic acid and 3.8 g of tin (II) octoate heated to 130 0 C and homogenized for 30 min. It was then cooled to 80 0 C, 480 g of hexamethylene diisocyanate added with vigorous stirring, heated to 140 0 C using the exotherm and the mixture kept at this temperature until no more NCO groups could be determined.
- tin (II) octoate heated to 130 0 C and homogenized for 30 min. It was then cooled to 80 0 C, 480 g of hexamethylene diisocyanate added with vigorous stirring, heated to 140 0 C using the exotherm and the mixture kept at this temperature until no more NCO groups could be determined.
- the polyurethane thus obtained was cooled to 90 ° - 100 0 C, 47 g of dimethyl ethanolamine (degree of neutralization 60%) was added, homogenized for 15 minutes and dispersed with 2270 g of demineralized water.
- the polyurethane thus obtained was cooled to 90 ° - 100 0 C, 39 g dimethylethanolamine (degree of neutralization 50%) was added, homogenized for 15 minutes with 2270th dispersed demineralized water.
- Unpainted polycarbonate film (film thickness: 175 ⁇ m)
- the scratch resistance was performed with a Crockmeter Atlas CM6.
- the film surface was scratched with a polishing paper (9 ⁇ m, 10 or 40 double strokes).
- Load duration 24 h at room temperature The assessment of the loaded film surface is carried out according to DIN 53230.
- DIN 53230 gives a relative rating scale for visual matching:
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Materials For Medical Uses (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10706146A EP2396357A1 (de) | 2009-02-10 | 2010-02-05 | 2k-polyurethan-lack für trägerfolien |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09001801A EP2216353A1 (de) | 2009-02-10 | 2009-02-10 | Trägerfolie mit Polyurethan-Beschichtung |
PCT/EP2010/000957 WO2010091898A1 (de) | 2009-02-10 | 2010-02-05 | 2k-polyurethan-lack für trägerfolien |
EP10706146A EP2396357A1 (de) | 2009-02-10 | 2010-02-05 | 2k-polyurethan-lack für trägerfolien |
Publications (1)
Publication Number | Publication Date |
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EP2396357A1 true EP2396357A1 (de) | 2011-12-21 |
Family
ID=40888049
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Application Number | Title | Priority Date | Filing Date |
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EP09001801A Withdrawn EP2216353A1 (de) | 2009-02-10 | 2009-02-10 | Trägerfolie mit Polyurethan-Beschichtung |
EP10706146A Withdrawn EP2396357A1 (de) | 2009-02-10 | 2010-02-05 | 2k-polyurethan-lack für trägerfolien |
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Application Number | Title | Priority Date | Filing Date |
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EP09001801A Withdrawn EP2216353A1 (de) | 2009-02-10 | 2009-02-10 | Trägerfolie mit Polyurethan-Beschichtung |
Country Status (6)
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US (1) | US20120059118A1 (de) |
EP (2) | EP2216353A1 (de) |
JP (1) | JP2012517489A (de) |
KR (1) | KR20110119694A (de) |
CN (1) | CN102317334A (de) |
WO (2) | WO2010091898A1 (de) |
Families Citing this family (12)
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BR112014019463A8 (pt) * | 2012-02-17 | 2017-07-11 | Akzo Nobel Coatings Int Bv | Película laminada de tinta termoformável; e processo de fornecimento de um substrato com superfície de toque suave e baixo brilho |
TWI548655B (zh) * | 2012-10-22 | 2016-09-11 | 積水特殊化學美國有限責任公司 | 用於嚴苛化學品包裝的聚乙烯吡咯啶酮(pvp)共聚物 |
DE102012110327A1 (de) * | 2012-10-29 | 2014-04-30 | Bayer Materialscience Aktiengesellschaft | Verformbare Folie |
CA2889543C (en) * | 2012-10-29 | 2020-09-15 | Bayer Materialscience Ag | Coating agent for mattable coatings |
CN105358602B (zh) | 2013-07-08 | 2018-12-04 | 旭化成株式会社 | 改性的树脂和树脂组合物 |
EP2937368A1 (de) * | 2014-04-24 | 2015-10-28 | BASF Coatings GmbH | Wässrige zweikomponenten-beschichtungszusammensetzungen und daraus hergestellte beschichtungen mit hoher erosionsbeständigkeit |
EP3109269B1 (de) | 2015-06-25 | 2018-10-31 | Covestro Deutschland AG | Harnstofffreie polyurethan-dispersionen |
WO2017058504A1 (en) * | 2015-10-02 | 2017-04-06 | Resinate Materials Group, Inc. | High performance coatings |
JP6586660B2 (ja) * | 2015-12-28 | 2019-10-09 | 花王株式会社 | 水系インク |
CN107892758B (zh) * | 2017-11-30 | 2021-04-30 | Ppg涂料(天津)有限公司 | 水性柔软触感涂料组合物和由其形成的耐磨涂层 |
EP4534618A1 (de) * | 2023-10-03 | 2025-04-09 | SABIC Global Technologies B.V. | Beschichteter artikel |
WO2025073844A1 (en) * | 2023-10-03 | 2025-04-10 | Sabic Global Technologies B.V. | Coated article |
Family Cites Families (18)
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DE1300266B (de) | 1960-06-10 | 1969-07-31 | Bayer Ag | Verfahren zur Herstellung hochmolekularer, linearer Polycarbonate |
DE1495730B2 (de) | 1963-07-24 | 1971-03-18 | Farbenfabriken Bayer AG, 5090 Le verkusen | Verfahren zum herstellen thermoplastischer polykondensations produkte |
US3737409A (en) | 1971-03-08 | 1973-06-05 | Gen Electric | Copolycarbonate of bis-3,5-dimethyl-4-hydroxyphenyl)sulfone with bisphenol-a |
US4108814A (en) | 1974-09-28 | 1978-08-22 | Bayer Aktiengesellschaft | Aqueous polyurethane dispersions from solvent-free prepolymers using sulfonate diols |
DE3840542C1 (en) | 1988-12-01 | 1989-11-02 | Curt 8122 Penzberg De Niebling | Process for producing a thin-walled, thermoformed plastic moulding and its use |
DE4136618A1 (de) | 1991-11-07 | 1993-05-13 | Bayer Ag | Wasserdispergierbare polyisocyanatgemische |
DE4406159A1 (de) * | 1994-02-25 | 1995-08-31 | Bayer Ag | Wäßrige Polyester-Polyurethan-Dispersionen und ihre Verwendung in Beschichtungsmitteln |
ATE252122T1 (de) | 1998-05-22 | 2003-11-15 | Bayer Ag | Wasserdispergierbare polyether-modifizierte polyisocyanatgemische |
US6143839A (en) | 1998-09-14 | 2000-11-07 | General Electric Company | Weatherable blends of polycarbonates with arylate polymers |
ES2214046T3 (es) | 1998-10-29 | 2004-09-01 | General Electric Company | Copoliestercarbonatos de bloque resistentes a la intemperie y mezclas que los contienen. |
DE10007821A1 (de) | 2000-02-21 | 2001-08-23 | Bayer Ag | Wasserdispergierbare Polyisocyanatgemische |
DE10024624A1 (de) | 2000-05-18 | 2001-11-22 | Bayer Ag | Modifizierte Polyisocyanate |
DE10130882A1 (de) | 2001-06-27 | 2003-01-16 | Bayer Ag | Verfahren zur Herstellung von aliphatischen Oligocarbonatdiolen |
DE10251797A1 (de) * | 2002-11-07 | 2004-05-19 | Bayer Ag | Polyurethanharz mit hohem Carbonatgruppengehalt |
DE10321149A1 (de) | 2003-05-12 | 2004-12-02 | Bayer Materialscience Ag | Ytterbium(III)acetylacetonat als Katalysator zur Herstellung von aliphatischen Oligocarbonatpolyolen |
AT412648B (de) * | 2003-06-27 | 2005-05-25 | Surface Specialties Austria | Wasserverdünnbare polyurethandispersionen |
DE102004055363A1 (de) | 2004-04-16 | 2005-11-10 | Karl Wörwag Lack- Und Farbenfabrik Gmbh & Co. Kg | Flexibler Schichtverbund mit einem Träger und einer darauf angebrachten Schicht härtbaren Lackes |
DE102004049592A1 (de) * | 2004-10-12 | 2006-05-04 | Bayer Materialscience Ag | Mit Soft-Touch-Lack beschichtete, verformbare Kunststoffverbundfolien und Kunststoffverbundelemente sowie deren Herstellung |
-
2009
- 2009-02-10 EP EP09001801A patent/EP2216353A1/de not_active Withdrawn
-
2010
- 2010-02-05 JP JP2011548623A patent/JP2012517489A/ja not_active Withdrawn
- 2010-02-05 US US13/147,477 patent/US20120059118A1/en not_active Abandoned
- 2010-02-05 WO PCT/EP2010/000957 patent/WO2010091898A1/de active Application Filing
- 2010-02-05 EP EP10706146A patent/EP2396357A1/de not_active Withdrawn
- 2010-02-05 WO PCT/EP2010/000716 patent/WO2010091823A1/de active Application Filing
- 2010-02-05 CN CN2010800072283A patent/CN102317334A/zh active Pending
- 2010-02-05 KR KR1020117018528A patent/KR20110119694A/ko not_active Withdrawn
Non-Patent Citations (2)
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None * |
See also references of WO2010091898A1 * |
Also Published As
Publication number | Publication date |
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WO2010091823A1 (de) | 2010-08-19 |
EP2216353A1 (de) | 2010-08-11 |
WO2010091898A8 (de) | 2011-08-18 |
WO2010091898A1 (de) | 2010-08-19 |
CN102317334A (zh) | 2012-01-11 |
KR20110119694A (ko) | 2011-11-02 |
JP2012517489A (ja) | 2012-08-02 |
US20120059118A1 (en) | 2012-03-08 |
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