KR101132250B1 - 가교제로서 사용될, 유기 용매들을 포함하지 않는 안정한수용성 폴리카보디이미드 분산체들의 제조방법 - Google Patents
가교제로서 사용될, 유기 용매들을 포함하지 않는 안정한수용성 폴리카보디이미드 분산체들의 제조방법 Download PDFInfo
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- KR101132250B1 KR101132250B1 KR1020057022052A KR20057022052A KR101132250B1 KR 101132250 B1 KR101132250 B1 KR 101132250B1 KR 1020057022052 A KR1020057022052 A KR 1020057022052A KR 20057022052 A KR20057022052 A KR 20057022052A KR 101132250 B1 KR101132250 B1 KR 101132250B1
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- polycarbodiimide
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- diisocyanate
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- 239000006185 dispersion Substances 0.000 title claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 21
- 239000003431 cross linking reagent Substances 0.000 title claims abstract description 7
- 239000003960 organic solvent Substances 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 150000001718 carbodiimides Chemical class 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 10
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 10
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 10
- 150000001412 amines Chemical class 0.000 claims abstract description 9
- 238000000576 coating method Methods 0.000 claims abstract description 8
- 239000000872 buffer Substances 0.000 claims abstract description 7
- 239000011347 resin Substances 0.000 claims abstract description 7
- 229920005989 resin Polymers 0.000 claims abstract description 7
- 239000011248 coating agent Substances 0.000 claims abstract description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 238000001704 evaporation Methods 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims abstract description 3
- 239000000758 substrate Substances 0.000 claims abstract description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract 2
- 229920005862 polyol Polymers 0.000 claims description 13
- 150000003077 polyols Chemical class 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 8
- 229920000768 polyamine Polymers 0.000 claims description 8
- IUUONVQOMMQAEH-UHFFFAOYSA-N 1-methyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CP1(=O)CCC=C1 IUUONVQOMMQAEH-UHFFFAOYSA-N 0.000 claims description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 6
- 125000005442 diisocyanate group Chemical group 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 6
- -1 hydroxy alkylsulfonates Chemical class 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000005270 trialkylamine group Chemical group 0.000 claims description 4
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 2
- 229920002292 Nylon 6 Polymers 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920005906 polyester polyol Polymers 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims 1
- 229920001155 polypropylene Polymers 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 239000004971 Cross linker Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 4
- 238000013112 stability test Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002433 hydrophilic molecules Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-O N-dimethylethanolamine Chemical compound C[NH+](C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-O 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- GWLWWNLFFNJPDP-UHFFFAOYSA-M sodium;2-aminoethanesulfonate Chemical group [Na+].NCCS([O-])(=O)=O GWLWWNLFFNJPDP-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
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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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
-
- 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/025—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing carbodiimide groups
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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
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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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
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- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
Claims (13)
- 가교제로서 사용될, 유기 용매들을 포함하지 않는 50℃에서 적어도 8주 동안 안정한 수용성 폴리카보디이미드 분산체들의 제조방법으로서:- 폴리카보디이미드를 형성하기 위해서 카보디이미드 형성 촉매의 존재 하에 폴리이소시아네이트를 반응시키고,- 상기 폴리카보디이미드 형성 동안 또는 그 후에 친수성 기, 및 아민 또는 히드록시 작용기 또는 이들의 혼합을 포함하는 화합물을 첨가하여 폴리카보디이미드 사슬을 종료시키거나, 상기 폴리카보디이미드 형성 동인 또는 그 후에 친수성 기, 및 아민 작용기, 히드록시 작용기, 아민 및 히드록시 작용기 또는 이들의 혼합을 포함하는 화합물을 첨가하여 폴리카보디이미드 사슬을 연장시키며,- 결과물인 화합물을 물에 분산시키며,여기에서 분산체를 위해 사용되는 물 또는 상기 수득된 수용성 분산체 또는 이 둘 모두에 염기 또는 완충액 또는 이들의 혼합에 첨가하여 pH가 9 내지 14 사이에서 조절되며,여기에서 친수성 기 및 하나 이상의 아민 작용기를 포함하는 화합물로 사슬을 종료시키거나 연장시키는 것은 폴리카보디이미드를 물에 분산시키는 동안 또는 그 후에 일어나는 것을 특징으로 하는, 안정한 수용성 폴리카보디이미드 분산체들의 제조방법.
- 삭제
- 제1항에 있어서,상기 폴리카보디이미드 분산체들의 pH는 11과 13 사이의 값으로 조절되는 것을 특징으로 하는, 안정한 수용성 폴리카보디이미드 분산체들의 제조방법.
- 제1항에 있어서,상기 카보디이미드 형성 촉매는 1-메틸포스폴렌-1-옥시드인 것을 특징으로 하는, 안정한 수용성 폴리카보디이미드 분산체들의 제조방법.
- 제1항에 있어서,상기 폴리카보디이미드를 제조하기 위해 사용되는 폴리이소시아네이트는 톨루엔-2,4-디이소시아네이트, 톨루엔-2,6-디이소시아네이트 및 그들의 혼합물들, 디페닐메탄-4,4'-디이소시아네이트, 1,4-페닐렌디이소시아네이트, 디시클로헥실메탄-4, 4'-디이소시아네이트, 3-이소시아나토메틸-3,5,5-트리메틸시클로헥실이소시아네이트, 1,6-헥실디이소시아네이트, 1,4-시클로헥실디이소시아네이트, 노르보닐디이소시아네이트, 또는 그들의 혼합물인 것을 특징으로 하는, 안정한 수용성 폴리카보디이미드 분산체들의 제조방법.
- 제1항에 있어서,상기 폴리이소시아네이트는 디시클로헥실메탄-4,4'-디이소시아네이트인 것을 특징으로 하는, 안정한 수용성 폴리카보디이미드 분산체들의 제조방법.
- 제1항에 있어서,상기 염기는 수산화 리튬, 수산화 나트륨, 수산화 칼륨, 또는 트리알킬아민, 또는 수산화 작용기들을 포함하는 트리알킬아민인 알칼리 수산화물(alkali hydroxyde)인 것을 특징으로 하는, 안정한 수용성 폴리카보디이미드 분산체들의 제조방법.
- 제1항에 있어서,상기 염기는 상기 폴리카보디이미드 사슬을 디알킬아미노알킬아민 또는 디알킬아미노알킬알코올로 캡핑(capping)하거나, 또는 폴리카보디이미드 형성 동안 또는 그 후에 디이소시아네이트에 대해 0.01-0.3 당량의 폴리올 또는 폴리아민을 포함하는 3차 아민을 첨가하는 것에 의해 폴리카보디이미드 사슬에 결합되는 것을 특징으로 하는, 안정한 수용성 폴리카보디이미드 분산체들의 제조방법.
- 제1항에 있어서,상기 완충액이 활성화되는 pH 범위는 9와 14 사이인 것을 특징으로 하는, 안정한 수용성 폴리카보디이미드 분산체들의 제조방법.
- 제1항에 있어서,상기 친수성 기, 및 하나 또는 그 이상의 아민 또는 수산화 작용기들 또는 이들의 혼합을 포함하는 화합물은 폴리에톡시 모노올 또는 폴리에톡시 디올, 폴리에톡시/폴리프로폭시 모노올 또는 폴리에톡시/폴리프로폭시 디올, 폴리에톡시 모노아민 또는 폴리에톡시 디아민, 폴리에톡시/폴리프로폭시 모노아민 또는 폴리에톡시/폴리프로폭시 디아민, 폴리알콕시 곁사슬을 가지는 디올 또는 디아민, 히드록시 알킬술포네이트 또는 아민 알킬술포네이트, 또는 디알킬아미노알킬 알코올 또는 디알킬아미노알킬 아민 또는 그들의 혼합물인 것을 특징으로 하는, 안정한 수용성 폴리카보디이미드 분산체들의 제조방법.
- 제1항에 있어서,상기 폴리카보디이미드 형성 전 또는 그동안 또는 그 후에 상기 폴리이소시아네이트에 대해 0.01-0.30 당량의 모노올 또는 폴리올 또는 모노아민 또는 폴리아민이 첨가되고, 상기 폴리올 또는 폴리아민은 폴리히드록시-알칸, 폴리에테르 폴리올, 폴리에스테르 폴리올, 폴리카보네이트 폴리올, 폴리카프로락탐 폴리올, 폴리아미노-알칸 및 폴리에테르 폴리아민 중에서 선택되는 것을 특징으로 하는, 안정한 수용성 폴리카보디이미드 분산체들의 제조방법.
- 카르복시산 작용기들을 포함하는 수용성 수지 및 가교제로서 제1항, 제3항, 제4항, 제5항, 제6항, 제7항, 제8항, 제9항, 제10항 및 제11항 중 어느 한 항에 따라 수득되는 폴리카보디이미드 분산체들을 포함하는 코팅 혼합물.
- 제 12항의 코팅 혼합물을 기판에 도포하고 물을 증발시켜서 얻어지는 경화된 물질.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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NL1023817A NL1023817C2 (nl) | 2003-07-03 | 2003-07-03 | Werkwijze voor de bereiding van stabiele polycarbodiimide dispersies in water, welke geen organische oplosmiddelen bevatten en als vernettingsmiddel kunnen worden gebruikt. |
NL1023817 | 2003-07-03 | ||
PCT/NL2004/000470 WO2005003204A2 (en) | 2003-07-03 | 2004-07-02 | Process for the preparation of stable polycarbodiimide dispersions in water, which are free of organic solvents and may be used as crosslinking agent |
Publications (2)
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KR20060017609A KR20060017609A (ko) | 2006-02-24 |
KR101132250B1 true KR101132250B1 (ko) | 2012-04-02 |
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KR1020057022052A KR101132250B1 (ko) | 2003-07-03 | 2004-07-02 | 가교제로서 사용될, 유기 용매들을 포함하지 않는 안정한수용성 폴리카보디이미드 분산체들의 제조방법 |
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US (1) | US7439316B2 (ko) |
EP (1) | EP1644428B2 (ko) |
JP (1) | JP5035792B2 (ko) |
KR (1) | KR101132250B1 (ko) |
CN (1) | CN100543056C (ko) |
AU (1) | AU2004253814B2 (ko) |
BR (1) | BRPI0411732B1 (ko) |
CA (1) | CA2531230C (ko) |
DK (1) | DK1644428T4 (ko) |
ES (1) | ES2466382T3 (ko) |
HK (1) | HK1094215A1 (ko) |
MX (1) | MXPA05013947A (ko) |
NL (1) | NL1023817C2 (ko) |
PL (1) | PL1644428T5 (ko) |
PT (1) | PT1644428E (ko) |
RU (1) | RU2313541C2 (ko) |
WO (1) | WO2005003204A2 (ko) |
ZA (1) | ZA200509360B (ko) |
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HK1094215A1 (en) | 2007-03-23 |
JP2007521360A (ja) | 2007-08-02 |
NL1023817C2 (nl) | 2005-01-04 |
RU2313541C2 (ru) | 2007-12-27 |
WO2005003204A2 (en) | 2005-01-13 |
PL1644428T3 (pl) | 2014-09-30 |
BRPI0411732A (pt) | 2006-08-08 |
CA2531230A1 (en) | 2005-01-13 |
CA2531230C (en) | 2011-01-18 |
EP1644428B2 (en) | 2024-05-08 |
JP5035792B2 (ja) | 2012-09-26 |
US20060106189A1 (en) | 2006-05-18 |
AU2004253814A1 (en) | 2005-01-13 |
DK1644428T3 (da) | 2014-06-23 |
RU2005141416A (ru) | 2006-08-10 |
US7439316B2 (en) | 2008-10-21 |
MXPA05013947A (es) | 2006-07-03 |
CN1805984A (zh) | 2006-07-19 |
WO2005003204A3 (en) | 2005-03-10 |
PT1644428E (pt) | 2014-06-24 |
PL1644428T5 (pl) | 2024-07-15 |
EP1644428A2 (en) | 2006-04-12 |
EP1644428B1 (en) | 2014-04-16 |
BRPI0411732B1 (pt) | 2014-12-16 |
KR20060017609A (ko) | 2006-02-24 |
CN100543056C (zh) | 2009-09-23 |
ES2466382T3 (es) | 2014-06-10 |
DK1644428T4 (da) | 2024-05-27 |
ZA200509360B (en) | 2007-04-25 |
AU2004253814B2 (en) | 2009-12-17 |
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