ES2347715T3 - Policarbonatos de alta funcionalidad, hiperramificados asi como su elaboracion y utilizacion. - Google Patents
Policarbonatos de alta funcionalidad, hiperramificados asi como su elaboracion y utilizacion. Download PDFInfo
- Publication number
- ES2347715T3 ES2347715T3 ES07787685T ES07787685T ES2347715T3 ES 2347715 T3 ES2347715 T3 ES 2347715T3 ES 07787685 T ES07787685 T ES 07787685T ES 07787685 T ES07787685 T ES 07787685T ES 2347715 T3 ES2347715 T3 ES 2347715T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- hyperbranched
- hyperbranched polycarbonates
- groups
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000004417 polycarbonate Substances 0.000 title claims abstract description 98
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 75
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 33
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 29
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 17
- 125000006850 spacer group Chemical group 0.000 claims abstract description 15
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000524 functional group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 150000008366 benzophenones Chemical class 0.000 claims abstract description 5
- 239000012948 isocyanate Substances 0.000 claims abstract description 5
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 4
- 239000004593 Epoxy Substances 0.000 claims abstract description 4
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 4
- 239000012965 benzophenone Substances 0.000 claims abstract description 4
- -1 optionally oxidized Chemical group 0.000 claims description 82
- 229920006324 polyoxymethylene Polymers 0.000 claims description 43
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 39
- 239000004922 lacquer Substances 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 239000003381 stabilizer Substances 0.000 claims description 16
- 239000000654 additive Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000000976 ink Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 238000007639 printing Methods 0.000 claims description 8
- 229920001169 thermoplastic Polymers 0.000 claims description 7
- 239000004416 thermosoftening plastic Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 235000011187 glycerol Nutrition 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000001301 oxygen Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 38
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- 238000007872 degassing Methods 0.000 description 39
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 31
- 239000000203 mixture Substances 0.000 description 30
- 239000000178 monomer Substances 0.000 description 30
- 238000006116 polymerization reaction Methods 0.000 description 29
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 230000001143 conditioned effect Effects 0.000 description 12
- 239000003999 initiator Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 238000005227 gel permeation chromatography Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000000412 dendrimer Substances 0.000 description 9
- 229920000736 dendritic polymer Polymers 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 7
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 238000006068 polycondensation reaction Methods 0.000 description 7
- 241000220317 Rosa Species 0.000 description 6
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- 235000011118 potassium hydroxide Nutrition 0.000 description 6
- 230000000750 progressive effect Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229920000965 Duroplast Polymers 0.000 description 5
- 239000004638 Duroplast Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 229920000587 hyperbranched polymer Polymers 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical compound CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 description 4
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical group NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 150000004292 cyclic ethers Chemical group 0.000 description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 238000001542 size-exclusion chromatography Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000012662 bulk polymerization Methods 0.000 description 3
- 125000005587 carbonate group Chemical group 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000011552 falling film Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000003017 thermal stabilizer Substances 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- XUXUHDYTLNCYQQ-UHFFFAOYSA-N 4-amino-TEMPO Chemical group CC1(C)CC(N)CC(C)(C)N1[O] XUXUHDYTLNCYQQ-UHFFFAOYSA-N 0.000 description 2
- INCCMBMMWVKEGJ-UHFFFAOYSA-N 4-methyl-1,3-dioxane Chemical compound CC1CCOCO1 INCCMBMMWVKEGJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
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- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- HAJIOQHUJLPSAL-UHFFFAOYSA-N tris(2,2,6,6-tetramethylpiperidin-4-yl) benzene-1,3,5-tricarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)C1=CC(C(=O)OC2CC(C)(C)NC(C)(C)C2)=CC(C(=O)OC2CC(C)(C)NC(C)(C)C2)=C1 HAJIOQHUJLPSAL-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- GKODZWOPPOTFGA-UHFFFAOYSA-N tris(hydroxyethyl)aminomethane Chemical compound OCCC(N)(CCO)CCO GKODZWOPPOTFGA-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000010457 zeolite Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
- C08G64/0216—Aliphatic polycarbonates saturated containing a chain-terminating or -crosslinking agent
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
- C08G64/0225—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/302—General preparatory processes using carbonates and cyclic ethers
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/305—General preparatory processes using carbonates and alcohols
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
-
- 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
- C09D169/00—Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Paints Or Removers (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06117852 | 2006-07-26 | ||
| EP06117852 | 2006-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2347715T3 true ES2347715T3 (es) | 2010-11-03 |
Family
ID=38654618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07787685T Active ES2347715T3 (es) | 2006-07-26 | 2007-07-18 | Policarbonatos de alta funcionalidad, hiperramificados asi como su elaboracion y utilizacion. |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US20090281274A1 (https=) |
| EP (1) | EP2049584B1 (https=) |
| JP (1) | JP5322109B2 (https=) |
| CN (3) | CN101490133A (https=) |
| AT (1) | ATE474009T1 (https=) |
| BR (2) | BRPI0722423A2 (https=) |
| DE (1) | DE502007004412D1 (https=) |
| ES (1) | ES2347715T3 (https=) |
| MX (1) | MX2009000067A (https=) |
| WO (1) | WO2008012252A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20090097933A (ko) | 2006-12-15 | 2009-09-16 | 바스프 에스이 | 고분지형 폴리카르보네이트를 함유하는 중합체 분산액 |
| US8399554B2 (en) * | 2007-11-19 | 2013-03-19 | Basf Se | Use of highly branched polymers in polymer dispersions for gloss colours |
| BRPI0820427A2 (pt) * | 2007-11-19 | 2015-05-26 | Basf Se | Usos de pelo menos um polímero elevadamente ramificado, e de uma dispersão polimérica aquosa, método para produzir uma dispersão polimérica aquosa, dispersão polimérica aquosa, composição aglutinante, agente de revestimento na forma de uma composição aquosa, e, método para aperfeiçoar a estabilidade de congelamento / descongelamento de uma dispersão polimérica aquosa |
| JP5431352B2 (ja) | 2007-11-28 | 2014-03-05 | ビーエーエスエフ ソシエタス・ヨーロピア | 液体安定剤混合物 |
| JP2009191194A (ja) * | 2008-02-15 | 2009-08-27 | Jsr Corp | ポリカーボネートの製造方法 |
| CN102665669B (zh) * | 2009-11-26 | 2014-04-16 | 巴斯夫欧洲公司 | 超支化聚碳酸酯在化妆品和皮肤病配制剂中的用途 |
| WO2012140175A1 (en) * | 2011-04-15 | 2012-10-18 | Basf Se | Hyperbranched polyesters in printing inks |
| EP2876126A1 (en) * | 2013-11-25 | 2015-05-27 | Basf Se | A stabilizer mixture |
| JP6497695B2 (ja) * | 2014-11-25 | 2019-04-10 | 関西ペイント株式会社 | 常温硬化性の耐候性塗料組成物 |
| JP6497697B2 (ja) * | 2015-01-30 | 2019-04-10 | 関西ペイント株式会社 | 常温硬化性の耐候性塗料組成物 |
| US9562135B1 (en) * | 2015-12-21 | 2017-02-07 | Covestro Llc | Polyether carbonates by DMC catalysis |
| CN107151316B (zh) * | 2017-06-20 | 2019-04-19 | 西北工业大学 | 能发射明亮荧光的羰基封端的超支化聚碳酸酯及制备方法 |
| CN111205905B (zh) * | 2020-01-31 | 2022-04-15 | 武汉材料保护研究所有限公司 | 一种酯类润滑油用多酚型抗氧剂及其制备方法 |
| CN113771391A (zh) * | 2021-11-01 | 2021-12-10 | 宁波嘉信化工实业有限公司 | 一种增强型低温热塑材料及其制备工艺 |
| CN119490646A (zh) * | 2023-08-17 | 2025-02-21 | 中国石油化工股份有限公司 | 一种超支化二氧化碳基聚碳酸酯及其制备方法和应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1402889A (en) * | 1973-02-03 | 1975-08-13 | Ciba Geigy Ag | Piperidine derivatives |
| US4087404A (en) | 1973-02-03 | 1978-05-02 | Ciba-Geigy Corporation | Polymers stabilized with substituted 2-(piperidinyl-4')-ethyl alcohol and salts thereof |
| US5359069A (en) * | 1989-03-21 | 1994-10-25 | Ciba-Geigy Corporation | Non-migrating 1-hydrocarbyloxy hindered amine derivatives as polymer stabilizers |
| JP3824024B2 (ja) * | 1995-07-26 | 2006-09-20 | 三菱瓦斯化学株式会社 | 高分子型酸化防止剤の製造法 |
| JPH09143161A (ja) * | 1995-09-22 | 1997-06-03 | Nippon Shokubai Co Ltd | 芳香族カルボン酸エステル、その製造方法およびその使用方法 |
| JP3228177B2 (ja) * | 1997-05-06 | 2001-11-12 | 富士ゼロックス株式会社 | 電子写真感光体および電子写真装置 |
| JP4072656B2 (ja) * | 1998-09-24 | 2008-04-09 | 三菱瓦斯化学株式会社 | 分岐化ポリカーボネートおよびその製造方法 |
| NL1013942C2 (nl) | 1999-12-23 | 2001-06-26 | Dsm Nv | Multifunctionele thermisch-oxidatieve stabilisator. |
| ES2525695T3 (es) | 2001-05-17 | 2014-12-29 | Basf Se | Aditivos de polímero con permanencia y afinidad superficial mejoradas |
| KR101178959B1 (ko) * | 2003-09-12 | 2012-08-31 | 바스프 에스이 | 고작용성의, 고분지형 또는 과분지형 폴리카르보네이트,이의 제법 및 용도 |
| DE102004051214A1 (de) * | 2004-10-20 | 2006-05-04 | Basf Ag | Fließfähige Polyoxymethylene |
| WO2007135032A2 (de) * | 2006-05-23 | 2007-11-29 | Basf Se | Verwendung von hyperverzweigten polycarbonaten als dispergiermittel für pigmente |
| WO2008009516A2 (de) * | 2006-07-20 | 2008-01-24 | Basf Se | Wasserbasislacke mit hochfunktionellen, hoch- oder hyperverzweigten polycarbonaten |
| KR20090097933A (ko) * | 2006-12-15 | 2009-09-16 | 바스프 에스이 | 고분지형 폴리카르보네이트를 함유하는 중합체 분산액 |
| US20130203958A1 (en) * | 2012-02-02 | 2013-08-08 | Basf Se | Polyoxymethylene copolymers |
-
2007
- 2007-07-18 CN CNA200780027626XA patent/CN101490133A/zh active Pending
- 2007-07-18 WO PCT/EP2007/057427 patent/WO2008012252A1/de not_active Ceased
- 2007-07-18 BR BRPI0722423-0A patent/BRPI0722423A2/pt not_active IP Right Cessation
- 2007-07-18 AT AT07787685T patent/ATE474009T1/de active
- 2007-07-18 DE DE502007004412T patent/DE502007004412D1/de active Active
- 2007-07-18 US US12/373,299 patent/US20090281274A1/en not_active Abandoned
- 2007-07-18 CN CN201210015407.2A patent/CN102585193B/zh active Active
- 2007-07-18 BR BRPI0715474-7A patent/BRPI0715474A2/pt not_active IP Right Cessation
- 2007-07-18 CN CN201510232281.8A patent/CN104910362A/zh active Pending
- 2007-07-18 MX MX2009000067A patent/MX2009000067A/es active IP Right Grant
- 2007-07-18 EP EP07787685A patent/EP2049584B1/de active Active
- 2007-07-18 JP JP2009521227A patent/JP5322109B2/ja not_active Expired - Fee Related
- 2007-07-18 ES ES07787685T patent/ES2347715T3/es active Active
-
2011
- 2011-09-09 US US13/229,094 patent/US8853331B2/en active Active
-
2014
- 2014-08-14 US US14/459,931 patent/US20140357833A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| MX2009000067A (es) | 2009-01-23 |
| JP5322109B2 (ja) | 2013-10-23 |
| ATE474009T1 (de) | 2010-07-15 |
| EP2049584A1 (de) | 2009-04-22 |
| EP2049584B1 (de) | 2010-07-14 |
| US20120065328A1 (en) | 2012-03-15 |
| BRPI0722423A2 (pt) | 2013-12-17 |
| CN102585193A (zh) | 2012-07-18 |
| CN102585193B (zh) | 2017-03-01 |
| US20090281274A1 (en) | 2009-11-12 |
| CN101490133A (zh) | 2009-07-22 |
| DE502007004412D1 (de) | 2010-08-26 |
| CN104910362A (zh) | 2015-09-16 |
| BRPI0715474A2 (pt) | 2012-02-28 |
| JP2009544782A (ja) | 2009-12-17 |
| US20140357833A1 (en) | 2014-12-04 |
| WO2008012252A1 (de) | 2008-01-31 |
| US8853331B2 (en) | 2014-10-07 |
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