JP5674821B2 - 抑泡作用を有するポリマー、および分散剤としてのその使用 - Google Patents
抑泡作用を有するポリマー、および分散剤としてのその使用 Download PDFInfo
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- JP5674821B2 JP5674821B2 JP2012554243A JP2012554243A JP5674821B2 JP 5674821 B2 JP5674821 B2 JP 5674821B2 JP 2012554243 A JP2012554243 A JP 2012554243A JP 2012554243 A JP2012554243 A JP 2012554243A JP 5674821 B2 JP5674821 B2 JP 5674821B2
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- Prior art keywords
- monomer
- polymer according
- polymer
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- ethylene oxide
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- 229920000642 polymer Polymers 0.000 title claims description 95
- 239000002270 dispersing agent Substances 0.000 title description 32
- 230000003254 anti-foaming effect Effects 0.000 title description 4
- 239000000178 monomer Substances 0.000 claims description 59
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 25
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 21
- 239000000725 suspension Substances 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 229910003480 inorganic solid Inorganic materials 0.000 claims description 15
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 239000002518 antifoaming agent Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000006185 dispersion Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- 150000003009 phosphonic acids Chemical class 0.000 claims description 2
- 239000000049 pigment Substances 0.000 description 38
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- 239000011734 sodium Substances 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 19
- 239000002202 Polyethylene glycol Substances 0.000 description 18
- 229920001223 polyethylene glycol Polymers 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 15
- 239000001023 inorganic pigment Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000004567 concrete Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000003973 paint Substances 0.000 description 12
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
- 239000004570 mortar (masonry) Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000004568 cement Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- 238000004519 manufacturing process Methods 0.000 description 9
- 239000011591 potassium Substances 0.000 description 9
- 229910052700 potassium Inorganic materials 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 125000000129 anionic group Chemical group 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 description 8
- 239000011707 mineral Substances 0.000 description 8
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- 238000006116 polymerization reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 235000012211 aluminium silicate Nutrition 0.000 description 7
- 239000003599 detergent Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000010276 construction Methods 0.000 description 6
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 229920005646 polycarboxylate Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
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- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
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- 238000010526 radical polymerization reaction Methods 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
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- 239000000843 powder Substances 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- 239000002455 scale inhibitor Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
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- 238000000576 coating method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
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- 238000005498 polishing Methods 0.000 description 1
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- FQLQNUZHYYPPBT-UHFFFAOYSA-N potassium;azane Chemical class N.[K+] FQLQNUZHYYPPBT-UHFFFAOYSA-N 0.000 description 1
- 239000011178 precast concrete Substances 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- RZKYDQNMAUSEDZ-UHFFFAOYSA-N prop-2-enylphosphonic acid Chemical compound OP(O)(=O)CC=C RZKYDQNMAUSEDZ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000011376 self-consolidating concrete Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229940077386 sodium benzenesulfonate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229940048842 sodium xylenesulfonate Drugs 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- HLPHHOLZSKWDAK-UHFFFAOYSA-M sodium;formaldehyde;naphthalene-1-sulfonate Chemical compound [Na+].O=C.C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HLPHHOLZSKWDAK-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910052566 spinel group Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RLQWHDODQVOVKU-UHFFFAOYSA-N tetrapotassium;silicate Chemical compound [K+].[K+].[K+].[K+].[O-][Si]([O-])([O-])[O-] RLQWHDODQVOVKU-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical class [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
- C08F220/286—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
- C08F220/288—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polypropylene-co-ethylene oxide in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F228/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
- C08F228/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur by a bond to sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Degasification And Air Bubble Elimination (AREA)
- Polyethers (AREA)
Description
(A)が式(I)
AはC2〜C4−アルキレンを表し、
BはAとは異なるC2〜C4−アルキレンを表し、
Rは水素またはメチルを表し、
mは1〜500の数を表し、
nは1〜500の数を表す]
で表されるモノマーであり、
(B)が、少なくとも1つのカルボン酸官能基を含むエチレン性不飽和モノマーであり、
(C)が、場合により、(A)および(B)とは異なる別のエチレン性不飽和モノマーであり、
(D)が式(II)
DはC2〜C4−アルキレンを表し、
EはDとは異なるC2〜C4−アルキレン基を表し、
FはEとは異なるC2〜C4−アルキレン基を表し、
Rは水素またはメチルを表し、
oは1〜500の数を表し、
pは1〜500の数を表し、
qは1〜500の数を表す]
で表されるモノマーであり、そして
モノマーの重量比が、モノマー(A)が35〜98.5%であり、モノマー(B)が0.5〜45%であり、モノマー(C)が0〜20%であり、そしてモノマー(D)が1〜20%である、
ポリマーに関する。
本願は、特許請求の範囲に記載の発明に関するものであるが、他の態様として以下も包含し得る。
1.モノマー(A)、(B)および(D)、および場合により(C)から誘導される構造単位を含有するポリマーであって、
(A)が式(I)[式中、AはC 2 〜C 4 −アルキレンを表し、BはAとは異なるC 2 〜C 4 −アルキレンを表し、Rは水素またはメチルを表し、mは1〜500の数を表し、nは1〜500の数を表す]で表されるモノマーであり、
(B)が、少なくとも1つのカルボン酸官能基を含むエチレン性不飽和モノマーであり、
(C)が、場合により、(A)および(B)とは異なる別のエチレン性不飽和モノマーであり、
(D)が式(II)[式中、DはC 2 〜C 4 −アルキレンを表し、EはDとは異なるC 2 〜C 4 −アルキレン基を表し、FはEとは異なるC 2 〜C 4 −アルキレン基を表し、
Rは水素またはメチルを表し、oは1〜500の数を表し、pは1〜500の数を表し、qは1〜500の数を表す]で表されるモノマーであり、そして
モノマーの重量比が、モノマー(A)が35〜98.5%であり、モノマー(B)が0.5〜45%であり、モノマー(C)が0〜20%であり、そしてモノマー(D)が1〜20%である、
ポリマー。
2.(A−O) m がプロピレンオキシド単位を、そして(B−O) n がエチレンオキシド単位を表すか、あるいは、(A−O) m がエチレンオキシド単位を、そして(B−O) n がプロピレンオキシド単位を表し、そして、前記エチレンオキシド単位のモル比が、全てのエチレンオキシド単位およびプロピレンオキシド単位(A−O) m および(B−O) n の合計(100%)を基準として50〜99%である、上記1記載のポリマー。
3.mが1〜150の数である、上記1または2に記載のポリマー。
4.nが3〜300の数である、上記1〜3のいずれか1つに記載のポリマー。
5.n+mが2〜500である、上記1〜4のいずれか1つに記載のポリマー。
6.モノマー(B)が、3〜8個のC原子を有するモノエチレン性不飽和モノカルボン酸およびジカルボン酸から選択される、上記1〜5のいずれか1つに記載のポリマー。
7.モノマー(C)が、モノエチレン性不飽和スルホン酸、ホスホン酸および/またはそれらの塩、ならびにモノアリルポリアルキレングリコールから選択される、上記1〜6のいずれか1つに記載のポリマー。
8.前記モノマー(C)が少なくとも0.5重量%の量で、そして前記モノマー(A)が最大で98重量%の量で存在する、上記1〜7のいずれか1つに記載のポリマー。
9.アルキレンオキシド単位(D−O) o 、(E−O) p および(F−O) q がブロック状に配置されており、そして(D−O) o がプロピレンオキシド単位、(E−O) p がエチレンオキシド単位、(F−O) q がプロピレンオキシド単位を表し、そして、前記エチレンオキシド単位のモル比が、エチレンオキシド単位およびプロピレンオキシド単位(D−O) o 、(E−O) p および(F−O) q の合計(100%)を基準として10〜90%である、上記1〜8のいずれか1つに記載のポリマー。
10.oが1〜100の数である、上記1〜9のいずれか1つに記載のポリマー。
11.pが1〜100の数である、上記1〜10のいずれか1つに記載のポリマー。
12.qが1〜100の数である、上記1〜11のいずれか1つに記載のポリマー。
13.o+p+qの合計が3〜500である、上記1〜12のいずれか1つに記載のポリマー。
14.10 3 g/mol〜10 9 g/mol、特に10 6 g/mol以下、殊に10 5 g/molの分子量を有する、上記1〜13のいずれか1つに記載のポリマー。
15.無機固体懸濁液の重量を基準として0.01〜15重量%の量にある上記1〜14のいずれか1つに記載のポリマーの、無機固体懸濁液のための消泡剤および分散剤としての使用。
16.無機固体懸濁液の重量を基準として0.01〜15重量%の量にある上記1〜14のいずれか1つに記載の少なくとも1種のポリマーを無機固体懸濁液に添加することによる、無機固体懸濁液の消泡および分散のための方法。
ポリグリコール1 ポリアルキレングリコールモノメタクリル酸エステル(式(I)、m=5、n=36〜38;(A−O)は(CH2CH(CH3)O))、(B−O)は(CH2CH2O)、モル質量約2,000 g/mol
ポリグリコール2 ポリアルキレングリコールモノメタクリル酸エステル(式(I)、m=5、n=104〜106;(A−O)は(CH2CH(CH3)O))、(B−O)は(CH2CH2O))、モル質量約5,000 g/mol。
ポリグリコール5 ポリアルキレングリコールモノメタクリル酸エステル(式(II)、o=4〜5、p=19〜21、q=15−17;(D−O)は[CH2CH(CH3)O)]、(E−O)は(CH2CH2O)、(F−O)は[CH2CH(CH3)O)]、モル質量約2,200 g/mol
ポリグリコール6 ポリアルキレングリコールモノメタクリル酸エステル(式(II)、o=4〜5、p=9〜11、q=15〜17;(D−O)は[CH2CH(CH3)O)]、(E−O)は(CH2CH2O)、(F−O)は[CH2CH(CH3)O)]、モル質量約1,700 g/mol
ポリグリコール7 ポリアルキレングリコールモノメタクリル酸エステル(式(II)、o=4〜5、p=19〜21、q=21〜23;(D−O)は[CH2CH(CH3)O)]、(E−O)は(CH2CH2O)、(F−O)は[CH2CH(CH3)O)]、モル質量約2,500 g/mol。
ガラスフラスコにおいて、モノマー(A)、モノマー(B)、モノマー(C)、モノマー(D)および調整剤(Regler)を溶剤中に、窒素下で仕込む。その後、反応混合物を75℃に加熱し、開始剤(6.35重量%の濃度が得られるように水に溶解した上述の量)を計り入れる。完全に添加した後に、さらに1時間75℃で撹拌する。引き続いて、室温まで冷却し、水酸化ナトリウム溶液(50重量%水溶液)を用いてpH値を5.5に調節する。ポリマー溶液を40%の活性成分含有量に調節した。
以下の例においては、特に言及しない限り、パーセント表示は重量パーセントである。
ポリマーの泡挙動を、フリット試験(Frittentest)によって調べ、モノマー(D)なしで製造したポリマーの泡挙動と比較した。試験溶液は、NaOH(0.8%)でpH12に調節され、CaCl2・2H2O(0.4%)で150°dHの水硬度に調節し、そしてTylose H100000(0.7%)で濃化した、完全に脱塩した水(98.1%)からなる。この溶液に、試験すべきポリマー溶液を加え(1Lの試験溶液に5gのポリマー溶液)、その後、フリットにより、30L/hの体積流量で空気を送り込んだ。泡形成を1分後に、続いて泡の崩壊を1、2および5分後に記録した。
モルタルにおける泡形成は、高い気泡含有率をもたらす。ポリマーに組み込まれたモノマー(D)の、モルタル中の泡の抑制における作用を示すために、これらのコポリマーを高流動化剤としてモルタルに添加し、気泡含有率を、このモノマー(D)を含まない対応のコポリマーを使用したモルタルのものと比較した。モルタルにおける気泡含有率の測定のために、まず、以下の組成を有するモルタルを製造した:
540g セメント(CEM II/A−S 32.5 R)
1350g CEN標準砂(DIN EN 196−1に従う)
221.5g 水
2.6g ポリマー溶液。
Claims (15)
- モノマー(A)、(B)および(D)、および場合により(C)から誘導される構造単位を含有するポリマーであって、
(A)が式(I)
AはC2〜C4−アルキレンを表し、
BはAとは異なるC2〜C4−アルキレンを表し、
Rは水素またはメチルを表し、
mは1〜500の数を表し、
nは1〜500の数を表す]
で表されるモノマーであり、
(B)が、3〜8個のC原子を有するモノエチレン性不飽和モノカルボン酸およびジカルボン酸から選択され、
(C)が、場合により、(A)および(B)とは異なる別のエチレン性不飽和モノマーであり、
(D)が式(II)
DはC2〜C4−アルキレンを表し、
EはDとは異なるC2〜C4−アルキレン基を表し、
FはEとは異なるC2〜C4−アルキレン基を表し、
Rは水素またはメチルを表し、
oは1〜500の数を表し、
pは1〜500の数を表し、
qは1〜500の数を表す]
で表されるモノマーであり、そして
モノマーの重量比が、モノマー(A)が35〜98.5%であり、モノマー(B)が0.5〜45%であり、モノマー(C)が0〜20%であり、そしてモノマー(D)が1〜20%である、
ポリマー。 - (A−O)mがプロピレンオキシド単位を、そして(B−O)nがエチレンオキシド単位を表すか、あるいは、(A−O)mがエチレンオキシド単位を、そして(B−O)nがプロピレンオキシド単位を表し、そして、前記エチレンオキシド単位のモル比が、全てのエチレンオキシド単位およびプロピレンオキシド単位(A−O)mおよび(B−O)nの合計(100%)を基準として50〜99%である、請求項1記載のポリマー。
- mが1〜150の数である、請求項1または2に記載のポリマー。
- nが3〜300の数である、請求項1〜3のいずれか1つに記載のポリマー。
- n+mが2〜500である、請求項1〜4のいずれか1つに記載のポリマー。
- モノマー(C)が、モノエチレン性不飽和スルホン酸、ホスホン酸および/またはそれらの塩、ならびにモノアリルポリアルキレングリコールから選択される、請求項1〜5のいずれか1つに記載のポリマー。
- 前記モノマー(C)が少なくとも0.5重量%の量で、そして前記モノマー(A)が最大で98重量%の量で存在する、請求項1〜6のいずれか1つに記載のポリマー。
- アルキレンオキシド単位(D−O)o、(E−O)pおよび(F−O)qがブロック状に配置されており、そして(D−O)oがプロピレンオキシド単位、(E−O)pがエチレンオキシド単位、(F−O)qがプロピレンオキシド単位を表し、そして、前記エチレンオキシド単位のモル比が、エチレンオキシド単位およびプロピレンオキシド単位(D−O)o、(E−O)pおよび(F−O)qの合計(100%)を基準として10〜90%である、請求項1〜7のいずれか1つに記載のポリマー。
- oが1〜100の数である、請求項1〜8のいずれか1つに記載のポリマー。
- pが1〜100の数である、請求項1〜9のいずれか1つに記載のポリマー。
- qが1〜100の数である、請求項1〜10のいずれか1つに記載のポリマー。
- o+p+qの合計が3〜500である、請求項1〜11のいずれか1つに記載のポリマー。
- 103g/mol〜109g/mol、特に106g/mol以下、殊に105g/molの分子量を有する、請求項1〜12のいずれか1つに記載のポリマー。
- 無機固体懸濁液の重量を基準として0.01〜15重量%の量にある請求項1〜13のいずれか1つに記載のポリマーの、無機固体懸濁液のための消泡剤および分散剤としての使用。
- 無機固体懸濁液の重量を基準として0.01〜15重量%の量にある請求項1〜13のいずれか1つに記載の少なくとも1種のポリマーを無機固体懸濁液に添加することによる、無機固体懸濁液の消泡および分散のための方法。
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DE102010009493A DE102010009493A1 (de) | 2010-02-26 | 2010-02-26 | Polymere und ihre Verwendung als Dispergiermittel mit schaumhemmender Wirkung |
DE102010009493.5 | 2010-02-26 | ||
PCT/EP2011/000684 WO2011103970A1 (de) | 2010-02-26 | 2011-02-15 | Polymere und ihre verwendung als dispergiermittel mit schaumhemmender wirkung |
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AU2017272533A1 (en) * | 2016-05-30 | 2018-11-22 | Gc Corporation | Method for kneading dental plaster powder |
CN111362612B (zh) * | 2018-12-26 | 2022-03-18 | 江苏苏博特新材料股份有限公司 | 一种堆石坝c15自密实混凝土专用聚羧酸减水剂 |
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DE1238831B (de) | 1965-01-09 | 1967-04-13 | Kao Corp | Verfahren zur Herstellung von leicht verteilbarem Zement |
DE1671017C3 (de) | 1966-02-11 | 1978-10-05 | Sueddeutsche Kalkstickstoff-Werke Ag, 8223 Trostberg | Anorganisch-organischer Baustoff |
DE2948698A1 (de) | 1979-12-04 | 1981-06-11 | Cempro Ag, Vaduz | Hydraulischer estrichmoertel |
DE3530258A1 (de) | 1985-08-23 | 1987-02-26 | Lentia Gmbh | Verwendung von salzen wasserloeslicher naphtalinsulfonsaeure-formaldehydkondensate als zusatzmittel fuer anorganische bindemittel und baustoff |
JP3184698B2 (ja) * | 1994-03-09 | 2001-07-09 | 花王株式会社 | コンクリート混和剤 |
DE19513126A1 (de) | 1995-04-07 | 1996-10-10 | Sueddeutsche Kalkstickstoff | Copolymere auf Basis von Oxyalkylenglykol-Alkenylethern und ungesättigten Dicarbonsäure-Derivaten |
DE19834173A1 (de) | 1997-08-01 | 1999-02-04 | Sueddeutsche Kalkstickstoff | Copolymere auf Basis von ungesättigten Dicarbonsäure-Derivaten und Oxyalkylenglykol-Alkenylethern |
DK0896123T3 (da) * | 1997-08-05 | 2005-10-31 | Inst Francais Du Petrole | Fremgangsmåde til forsinkelse af væksten og/eller agglomerationen af og eventuelt forsinkelse af dannelsen af hydrater i en produktionsudledning |
DE10017667A1 (de) | 2000-04-08 | 2001-10-18 | Goldschmidt Ag Th | Dispergiermittel zur Herstellung wässriger Pigmentpasten |
DE10017663A1 (de) | 2000-04-08 | 2001-10-11 | Basf Ag | Verfahren zur Herstellung eines geträgerten Katalysators zur Polymerisation von Olefinen |
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FR2810261B1 (fr) | 2000-06-15 | 2002-08-30 | Coatex Sa | Utilisation de copolymeres faiblement anioniques comme agent dispersant et/ou d'aide au broyage de suspension aqueuse de matieres minerales, suspensions aqueuses obtenues et leurs utilisations |
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US6582510B1 (en) | 2002-04-16 | 2003-06-24 | Arco Chemical Technology, L.P. | Use of comb-branched copolymers as pigment dispersants |
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DE102007039783A1 (de) * | 2007-08-23 | 2009-02-26 | Clariant International Ltd. | Wässrige Pigmentpräparationen mit anionischen Additiven auf Allyl- und Vinyletherbasis |
DE102007045230A1 (de) * | 2007-09-21 | 2009-04-09 | Clariant International Limited | Polycarboxylatether als Dispergiermittel für anorganische Pigmentformulierungen |
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DE102010009493A1 (de) | 2011-09-29 |
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CN102762620B (zh) | 2015-04-01 |
CN102762620A (zh) | 2012-10-31 |
PT2539383E (pt) | 2014-02-26 |
US8940832B2 (en) | 2015-01-27 |
ES2444508T3 (es) | 2014-02-25 |
EP2539383B1 (de) | 2013-12-11 |
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JP2013520538A (ja) | 2013-06-06 |
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