ZA200509360B - Process for the preparation of stable polycarbodiimide dispersions in water, which are free of organic solvents and may be used as crosslinking agent - Google Patents
Process for the preparation of stable polycarbodiimide dispersions in water, which are free of organic solvents and may be used as crosslinking agent Download PDFInfo
- Publication number
- ZA200509360B ZA200509360B ZA200509360A ZA200509360A ZA200509360B ZA 200509360 B ZA200509360 B ZA 200509360B ZA 200509360 A ZA200509360 A ZA 200509360A ZA 200509360 A ZA200509360 A ZA 200509360A ZA 200509360 B ZA200509360 B ZA 200509360B
- Authority
- ZA
- South Africa
- Prior art keywords
- process according
- polycarbodiimide
- mono
- diisocyanate
- amine
- Prior art date
Links
- 239000006185 dispersion Substances 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 13
- 239000003431 cross linking reagent Substances 0.000 title claims description 6
- 239000003960 organic solvent Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001718 carbodiimides Chemical class 0.000 claims description 13
- 229920005862 polyol Polymers 0.000 claims description 13
- 150000003077 polyols Chemical class 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000005056 polyisocyanate Substances 0.000 claims description 9
- 229920001228 polyisocyanate Polymers 0.000 claims description 9
- 150000001412 amines Chemical group 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229920000768 polyamine Polymers 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 7
- 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
- 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 6
- 125000005442 diisocyanate group Chemical group 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- -1 amine alkylsul- fonate Chemical class 0.000 claims description 5
- 239000000872 buffer Substances 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 230000006870 function Effects 0.000 claims 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 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 125000005270 trialkylamine group Chemical group 0.000 claims description 4
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 claims description 2
- 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
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 238000001704 evaporation Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group 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
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 229920005906 polyester polyol Polymers 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 description 6
- 239000004971 Cross linker Substances 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 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 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 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 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 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
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 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
- 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
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- 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)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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. |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200509360B true ZA200509360B (en) | 2007-04-25 |
Family
ID=33563077
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200509360A ZA200509360B (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 |
Country Status (18)
Country | Link |
---|---|
US (1) | US7439316B2 (fr) |
EP (1) | EP1644428B2 (fr) |
JP (1) | JP5035792B2 (fr) |
KR (1) | KR101132250B1 (fr) |
CN (1) | CN100543056C (fr) |
AU (1) | AU2004253814B2 (fr) |
BR (1) | BRPI0411732B1 (fr) |
CA (1) | CA2531230C (fr) |
DK (1) | DK1644428T4 (fr) |
ES (1) | ES2466382T3 (fr) |
HK (1) | HK1094215A1 (fr) |
MX (1) | MXPA05013947A (fr) |
NL (1) | NL1023817C2 (fr) |
PL (1) | PL1644428T3 (fr) |
PT (1) | PT1644428E (fr) |
RU (1) | RU2313541C2 (fr) |
WO (1) | WO2005003204A2 (fr) |
ZA (1) | ZA200509360B (fr) |
Families Citing this family (44)
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US8389113B2 (en) * | 2002-09-17 | 2013-03-05 | Ppg Industries Ohio, Inc. | Substrates and articles of manufacture coated with a waterborne 2K coating composition |
JP2006035190A (ja) * | 2004-07-30 | 2006-02-09 | Nisshinbo Ind Inc | 硬化塗膜の製造方法 |
NL1031053C2 (nl) * | 2006-02-02 | 2007-08-03 | Stahl Int Bv | Werkwijze voor de bereiding van dispersies van vernettingsmiddelen in water. |
JP2010530445A (ja) * | 2007-06-08 | 2010-09-09 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロアルキル含有エステルオリゴマーとポリジカルボジイミド(類)とのブレンド |
US20090246393A1 (en) * | 2008-03-27 | 2009-10-01 | Ppg Industries Ohio, Inc. | Polycarbodiimides |
WO2010028217A1 (fr) * | 2008-09-05 | 2010-03-11 | The Board Of Trustees Of The University Of Illinois | Réactifs de couplage de méthyléther-carbodiimide de poly(éthylèneglycol) pour la fonctionnalisation biologique et chimique de nanoparticules solubles dans l'eau |
US8900667B2 (en) * | 2009-12-18 | 2014-12-02 | Ppg Industries Ohio, Inc. | One-component, ambient curable waterborne coating compositions, related methods and coated substrates |
CN102869694B (zh) * | 2010-03-02 | 2015-09-02 | Ppg工业俄亥俄公司 | 单组分、环境能固化的水性涂料组合物,相关的方法和涂覆的基材 |
EP2371873A1 (fr) | 2010-04-01 | 2011-10-05 | Bayer MaterialScience AG | Procédé de carbodiimidation |
NL2005163C2 (nl) | 2010-07-28 | 2012-01-31 | Stahl Int Bv | Werkwijze voor de bereiding van multifunctionele polycarbodiimides, welke gebruikt worden als vernettingsmiddel. |
EP2423186B1 (fr) * | 2010-08-30 | 2017-05-31 | LANXESS Deutschland GmbH | Nouveau agent adhésif basé sur des carbodiimides, dispersions aqueouses et adhésives resorcinol-formaldéhyde-latex, fibres avec adhérence améliorée, leur procédé de préparation et leur application. |
JP5945172B2 (ja) * | 2011-06-29 | 2016-07-05 | 三洋化成工業株式会社 | 樹脂改質剤 |
EP2660258A1 (fr) * | 2012-05-03 | 2013-11-06 | Rhein Chemie Rheinau GmbH | Nouvelles compositions contenant des carbodiimides, un de leurs procédés de fabrication et d'utilisation |
PL2855579T3 (pl) | 2012-05-24 | 2016-09-30 | Wodne kompozycje środka wiążącego | |
JP5922499B2 (ja) * | 2012-05-31 | 2016-05-24 | 三洋化成工業株式会社 | 樹脂改質剤 |
WO2014044742A1 (fr) * | 2012-09-19 | 2014-03-27 | Basf Se | Procédé de purification d'un polycarbodiimide |
US20140242281A1 (en) | 2013-02-28 | 2014-08-28 | Ppg Industries Ohio, Inc. | Methods and compositions for coating substrates |
WO2016141227A1 (fr) * | 2015-03-03 | 2016-09-09 | Clear Technology Holdings, Llc | Système de revêtement de polymère de polyester mélangé à du polyuréthanne absorbant un rayonnement de lumière à base d'eau |
CA3173593A1 (fr) | 2015-05-30 | 2016-12-08 | Core Energy Recovery Solutions Inc. | Methode de fabrication d'une membrane de transport de vapeur d'eau soutenue comprenant un copolymere de polyoxyethylene |
TWI714606B (zh) * | 2015-07-08 | 2021-01-01 | 日商日清紡化學股份有限公司 | 碳化二亞胺系水性樹脂交聯劑 |
US10011677B2 (en) * | 2016-01-05 | 2018-07-03 | Mitsui Chemicals, Inc. | Polycarbodiimide composition, method for producing polycarbodiimide composition, aqueous dispersion composition, solution composition, resin composition, and cured resin |
WO2017122170A1 (fr) * | 2016-01-15 | 2017-07-20 | Ppg Industries Ohio, Inc. | Composition de revêtement comprenant une poudre dispersée dans un vecteur liquide |
US9957394B2 (en) | 2016-09-07 | 2018-05-01 | Ppg Industries Ohio, Inc. | Methods for preparing powder coating compositions |
JP6984838B2 (ja) | 2016-12-27 | 2021-12-22 | 日清紡ケミカル株式会社 | カルボキシル基含有水性樹脂組成物、成形体、及びポリカルボジイミド化合物の製造方法 |
EP3589713A4 (fr) | 2017-02-28 | 2020-12-30 | 3M Innovative Properties Company | Adhésif polyuréthane résistant aux produits chimiques |
CN111108245B (zh) * | 2017-09-25 | 2022-12-30 | Dic株式会社 | 合成皮革的制造方法 |
CN108003313B (zh) * | 2017-12-21 | 2020-08-04 | 上海朗亿功能材料有限公司 | 一种嵌段型聚碳化二亚胺水性交联剂及其制备方法 |
EP3502157A1 (fr) | 2017-12-21 | 2019-06-26 | Covestro Deutschland AG | Dispersion aqueuse de polycarbodiimide à stabilité au stockage accrue et son procédé de production |
JP7028401B2 (ja) | 2018-02-23 | 2022-03-02 | 日清紡ケミカル株式会社 | 水性カルボジイミド含有液の製造方法 |
CN108715628B (zh) * | 2018-06-22 | 2022-04-01 | 上海朗亿功能材料有限公司 | 一种脂环族聚碳化二亚胺抗水解剂及其制备方法 |
CN108863851A (zh) * | 2018-07-13 | 2018-11-23 | 成都创世芯研科技有限公司 | 一种支化型水性碳化二亚胺型交联剂及其制备方法 |
JP7402630B2 (ja) * | 2018-08-10 | 2023-12-21 | 三井化学株式会社 | ポリカルボジイミド組成物、ポリカルボジイミド組成物の製造方法、水分散組成物、溶液組成物、樹脂組成物および樹脂硬化物 |
EP3835333B1 (fr) * | 2018-08-10 | 2024-06-26 | Mitsui Chemicals, Inc. | Composition de polycarbodiimide, méthode de production de composition de polycarbodiimide, composition dispersée dans l'eau, composition de solution, composition de résine, produit durci en résine, et agent de réticulation carbodiimide pour le traitement des fibres |
PT3883735T (pt) | 2018-11-23 | 2023-11-15 | Basf Coatings Gmbh | Método automatizado para a moldagem por injeção de constituintes revestidos |
WO2020104214A1 (fr) | 2018-11-23 | 2020-05-28 | Basf Coatings Gmbh | Procédé de revêtement en moule (imc) avec pigmentation et démoulage automatique pour revêtir des substrats |
US20220010168A1 (en) | 2018-11-23 | 2022-01-13 | Basf Coatings Gmbh | Self-releasing in-mold coating (imc) for coating substrates |
ES2967999T3 (es) | 2018-11-23 | 2024-05-06 | Basf Coatings Gmbh | Procedimiento manual para el moldeo por inyección de componentes recubiertos |
CN113614170B (zh) * | 2019-03-22 | 2023-07-04 | 日清纺化学株式会社 | 粉体聚碳化二亚胺化合物和酯类树脂组合物 |
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CN111171702B (zh) * | 2020-01-17 | 2021-09-21 | 浙江佑谦特种材料有限公司 | 双重固化的聚氨酯水分散体及水性uv涂料 |
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EP4200367B1 (fr) | 2021-09-28 | 2024-07-10 | BASF Coatings GmbH | Procédé de revêtement d'un substrat à l'aide d'une composition de revêtement comprenant un pigment naturel |
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JP4559620B2 (ja) * | 1997-07-31 | 2010-10-13 | ビーエーエスエフ ソシエタス・ヨーロピア | ポリウレタンを含む潜在架橋性水性分散液 |
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-
2003
- 2003-07-03 NL NL1023817A patent/NL1023817C2/nl not_active IP Right Cessation
-
2004
- 2004-07-02 EP EP04748700.4A patent/EP1644428B2/fr not_active Expired - Lifetime
- 2004-07-02 WO PCT/NL2004/000470 patent/WO2005003204A2/fr active Application Filing
- 2004-07-02 CN CNB2004800163516A patent/CN100543056C/zh not_active Expired - Lifetime
- 2004-07-02 AU AU2004253814A patent/AU2004253814B2/en not_active Expired
- 2004-07-02 PT PT47487004T patent/PT1644428E/pt unknown
- 2004-07-02 RU RU2005141416/04A patent/RU2313541C2/ru not_active IP Right Cessation
- 2004-07-02 ES ES04748700.4T patent/ES2466382T3/es not_active Expired - Lifetime
- 2004-07-02 MX MXPA05013947A patent/MXPA05013947A/es active IP Right Grant
- 2004-07-02 JP JP2006516993A patent/JP5035792B2/ja not_active Expired - Lifetime
- 2004-07-02 DK DK04748700.4T patent/DK1644428T4/da active
- 2004-07-02 KR KR1020057022052A patent/KR101132250B1/ko active IP Right Grant
- 2004-07-02 ZA ZA200509360A patent/ZA200509360B/en unknown
- 2004-07-02 CA CA2531230A patent/CA2531230C/fr not_active Expired - Fee Related
- 2004-07-02 BR BRPI0411732-8A patent/BRPI0411732B1/pt active IP Right Grant
- 2004-07-02 PL PL04748700T patent/PL1644428T3/pl unknown
-
2005
- 2005-12-28 US US11/320,189 patent/US7439316B2/en active Active
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Also Published As
Publication number | Publication date |
---|---|
US7439316B2 (en) | 2008-10-21 |
JP5035792B2 (ja) | 2012-09-26 |
KR20060017609A (ko) | 2006-02-24 |
CA2531230C (fr) | 2011-01-18 |
CA2531230A1 (fr) | 2005-01-13 |
AU2004253814A1 (en) | 2005-01-13 |
KR101132250B1 (ko) | 2012-04-02 |
WO2005003204A3 (fr) | 2005-03-10 |
NL1023817C2 (nl) | 2005-01-04 |
HK1094215A1 (en) | 2007-03-23 |
PT1644428E (pt) | 2014-06-24 |
EP1644428A2 (fr) | 2006-04-12 |
RU2005141416A (ru) | 2006-08-10 |
BRPI0411732B1 (pt) | 2014-12-16 |
MXPA05013947A (es) | 2006-07-03 |
WO2005003204A2 (fr) | 2005-01-13 |
DK1644428T4 (da) | 2024-05-27 |
JP2007521360A (ja) | 2007-08-02 |
CN1805984A (zh) | 2006-07-19 |
EP1644428B2 (fr) | 2024-05-08 |
CN100543056C (zh) | 2009-09-23 |
AU2004253814B2 (en) | 2009-12-17 |
EP1644428B1 (fr) | 2014-04-16 |
US20060106189A1 (en) | 2006-05-18 |
PL1644428T3 (pl) | 2014-09-30 |
ES2466382T3 (es) | 2014-06-10 |
RU2313541C2 (ru) | 2007-12-27 |
BRPI0411732A (pt) | 2006-08-08 |
DK1644428T3 (da) | 2014-06-23 |
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