JP2005511825A - ポリエチレングリコール、ポリプロピレングリコール又はポリプロピレングリコールグリセリルエステル中のipbcの液状組成物 - Google Patents
ポリエチレングリコール、ポリプロピレングリコール又はポリプロピレングリコールグリセリルエステル中のipbcの液状組成物 Download PDFInfo
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- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical group CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 239000007788 liquid Substances 0.000 title claims abstract description 13
- 229920001223 polyethylene glycol Polymers 0.000 title claims abstract description 10
- 229920001451 polypropylene glycol Polymers 0.000 title claims abstract description 10
- 239000002202 Polyethylene glycol Substances 0.000 title claims abstract description 4
- 125000005908 glyceryl ester group Chemical group 0.000 title abstract 2
- 239000003973 paint Substances 0.000 claims abstract description 19
- 239000012855 volatile organic compound Substances 0.000 claims abstract description 16
- 238000000576 coating method Methods 0.000 claims abstract description 5
- 239000008199 coating composition Substances 0.000 claims description 5
- -1 3-iodo-2-propynylbutyl Chemical group 0.000 claims description 3
- 238000004042 decolorization Methods 0.000 claims description 2
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 238000002845 discoloration Methods 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract 1
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 description 45
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 26
- 238000009472 formulation Methods 0.000 description 18
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 8
- 238000000465 moulding Methods 0.000 description 4
- 238000004383 yellowing Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 230000036561 sun exposure Effects 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/205—Compounds containing groups, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Organic Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
- Cosmetics (AREA)
Abstract
Description
本出願は2001年12月12日付け出願の米国仮出願第60/341,110号に基づく。
1.発明の分野
本発明は、液状組成物に関し、それは、塗料及び被膜のVOCの原因にならず、脱色に対して安定であり、特に、3-ヨード-2-プロピニルブチルカルバメート(IPBC)と、ポリエチレングリコール(PEG)、又はプロピレングリコール(PPG)又はプロピレングリコールグリセリルエステル(PGGE)、又はそれらの組み合わせとの混合物である。
米国特許第4,276,211号;第4,552,885号;第5,938,825号;第6,059,991号及び第6,140,370号明細書で示されているように、種々の方法及び組成物は、IPBCを含有する生命破壊性(biocidal)組成物を、例えば、液体媒体中のUV(紫外線)吸収材及び/又は有機性エポキシドを用いて、安定化させることが記載されている。N-メチルピロリドン(NMP)、Texanol(R)(テキサノール)のエステルアルコール、及びジメチル酸化物(DMSO)のような有機溶媒はIPBC用の典型的な溶媒である。Singer(シンガー), W.は、米国特許第4,276,211号明細書において、例えば、カルバミン酸ヨードアルキンを含有する塗料組成物を記載しており、それは、選定されたエポキシ化合物の添加によって色を安定化させる。しかしながら、これらの文献は、どれも、揮発性有機化合物(VOC)においても低い安定なIPBCの組成物を提供しない。多くの司法管轄区においては、地方の規制当局が製品の使用の際に放出されるVOCの量に極めて低い下限を確立している。したがって、これらの司法管轄区において使用するために販売されるすべての物質中で添加剤のVOCを最小にすることが好ましい。
本明細書に記載されるものは、液状組成物であって、重量で、99.9〜50%のポリエチレングリコール、ポリプロピレングリコール又はポリプロピレングリコールグリセリル、又はそれらの混合物中の0.1〜50%のIPBCから本質的に成る液状組成物であり、これは、塗料及び被膜のVOCの原因にならず、及び高められた温度で又は直接日光の下でさえも脱色に対して効果的に安定化する。
本発明を次の例によってより一層詳細に例示する。部分及びパーセントに対するすべての言及は、特に示さない限り、重量に基づく。
本発明の組成物のNMPに対する比較試験(加熱)
溶液は、IPBCの40部を、上述したように、400の分子量を有するPEG(PEG400)又はN-メチルピロリドン(NMP)の60部中に溶解することによって得られた。次いで、溶液を20日間65℃で加熱し、及び溶液の色を、Gardner(ガードナー)の色スケールを用いて評価した。結果を表1に示す。
上記と同様(直射日光)
IPBCの40パーセント溶液を、例1で記載しているように調製した。次いで、溶液を85日間、直射日光に曝した。溶液の色の変化を、Gardner色スケールを用いて評価した。結果を表2に示す。
例1及び2の結果
例1及び例2からのIPBC溶液をHPLCによって分析した。結果を表3に示す。
PEG、PPG及びPGGE中のIPBCの安定性
溶液は、IPBCの20部を、前述のように、PEG-400又はN-メチルピロリドン(NMP)又はプロピレングリコール(PG)、又は脂肪酸メチルエステル(FAME)又はポリプロピレングリコールグリセリルエーテル(PGGE)又はポリプロピレングリコール425(PPG-425)の80部中で溶解することによって得られた。次いで、溶液を30日間50℃で加熱するか、又は直射日光に30日間曝した。すべての溶液をHPLCによって分析した。結果を表4に示す。
水性塗料配合物中のIPBCの安定性
60%のPEG-400中で40%のIPBCを含有する液状配合物を、例1に記載したように調製した。また、他の商業的に入手できる配合物(例えば、ISP からのFungitrol(R) 440、40%のIPBC) を、比較のために評価した。次いで、各IPBC配合物を、米国特許第4,276,211号明細書(Singer等、1981年)の第4欄、第36〜42行(“PAINTS”)に記載されている水性塗料配合物中に組み入れた。この水性塗料配合物はIPBCの存在において黄色を示した。IPBC配合物を含む塗料の試料を、50℃で2週間熱老化させた。乾燥フィルムの試料を、ドローダウン板紙上での3ミルの濡れたフィルムのキャスティング及び24時間の風乾によって調製した。黄変指標をASTM D-1925の方法に従って測定した。コントロール(IPBC配合を含まない塗料)とIPBC配合を有する塗料との間の黄変における差、ΔBを、各試験についての応答として算出した。結果を表5に示す。
IPBCを含有する液状配合物のVOC含量
20%のIPBC溶液を、上記の例で上述しているように、PEG、PPG又はPGGE中に溶解した。それぞれのVOC含量はASTM D-2369-98に従って決定し、及びいくつかの他の市販のIPBC配合物のための同じ試験条件下で定められたVOCレベルと比較した。結果を以下の表6に示す。
IPBCの液状組成物を含有する塗料のVOC含量
異なる20%のIPBC液状組成物の2.5gを、VOCにおいて低いと広告されている市販の塗料100gに添加した。次いで、様々なIPBCの液状組成物を含む塗料のVOC含量を、例6で記載しているように決定した。結果を表7に示す。
Claims (3)
- 液状組成物であって、重量で、99.9〜50%のポリエチレングリコール、ポリプロピレングリコール又はポリプロピレングリコールグリセリル、又はそれらの混合物中の0.1〜50%のIPBC(3−ヨード−2−プロピニルブチルカルバメート)から本質的に成り、塗料及び被膜のVOC(揮発性有機化合物)の原因にならず、及び高められた温度又は直射日光下においてさえ脱色に対し有効に安定化することを特徴とする液状組成物。
- 塗料又は被膜組成物中で安定化することを特徴とする請求項1記載の液状組成物。
- 水性塗料組成物中で安定化することを特徴とする請求項1記載の液状組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US34111001P | 2001-12-12 | 2001-12-12 | |
US60/341,110 | 2001-12-12 | ||
PCT/US2002/038797 WO2003049543A1 (en) | 2001-12-12 | 2002-12-06 | Liquid compositions of ipbc in polyethylene glycol, polypropylene glycol or polypropylene glycol glyceryl esters |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2005511825A true JP2005511825A (ja) | 2005-04-28 |
JP2005511825A5 JP2005511825A5 (ja) | 2006-03-02 |
JP5226171B2 JP5226171B2 (ja) | 2013-07-03 |
Family
ID=23336279
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003550598A Expired - Lifetime JP5226171B2 (ja) | 2001-12-12 | 2002-12-06 | ポリエチレングリコール、ポリプロピレングリコール又はポリプロピレングリコールグリセリルエステル中のipbcの液状組成物 |
Country Status (7)
Country | Link |
---|---|
US (1) | US6616740B2 (ja) |
EP (1) | EP1460899B1 (ja) |
JP (1) | JP5226171B2 (ja) |
KR (1) | KR20040073475A (ja) |
AU (1) | AU2002359604B2 (ja) |
CA (1) | CA2469449C (ja) |
WO (1) | WO2003049543A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012057008A (ja) * | 2010-09-07 | 2012-03-22 | Asahi Organic Chemicals Industry Co Ltd | ポリウレタンフォーム用発泡性組成物並びにポリウレタンフォーム材 |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2005200152B2 (en) * | 2004-01-16 | 2009-04-23 | Archer-Daniels-Midland Company | Improved color in film-forming compositions |
US20060013833A1 (en) * | 2004-07-16 | 2006-01-19 | Isp Investments Inc. | Thermal stabilization of biocides in matrix compositions processed at elevated temperatures |
US20070224135A1 (en) | 2006-03-24 | 2007-09-27 | Xianbin Liu | Stable aqueous suspension concentrate for delivery of UV-labile water-insoluble biocides |
US20100016390A1 (en) * | 2006-07-25 | 2010-01-21 | Pierre Marie Lenoir | Stable, low voc, low viscous biocidal formulations and method of making such formulations |
DE102007024208A1 (de) * | 2007-05-24 | 2008-11-27 | Lanxess Deutschland Gmbh | Iodpropargylverbindungen haltige Dispersionen |
TW200932107A (en) * | 2008-01-18 | 2009-08-01 | Dow Global Technologies Inc | Stable, low VOC, low viscous biocidal formulations and method of making such formulations |
EP2153722A1 (de) * | 2008-08-05 | 2010-02-17 | Lanxess Deutschland GmbH | Antifungische Flüssigformulierungen enthaltend 3-Iodpropargylbutylcarbamat (IPBC) und N-octylisothiazolinon (NOIT) |
WO2010142790A1 (de) * | 2009-06-12 | 2010-12-16 | Lanxess Deutschland Gmbh | Heterocyclische 3-ringverbindungen enthaltende anorganische trägermaterialien |
KR20240121836A (ko) * | 2021-12-17 | 2024-08-09 | 바스프 에스이 | 항미생물제 및 카르복스아미드를 포함하는 조성물 |
Family Cites Families (9)
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US4276211A (en) * | 1980-03-10 | 1981-06-30 | Troy Chemical Corporation | Stabilization composition for coating composition |
US4323602A (en) * | 1980-05-14 | 1982-04-06 | Roberts Consolidated Industries, Inc. | Water repellent and preservative for wood products |
JP3585176B2 (ja) * | 1992-07-22 | 2004-11-04 | シントーファイン株式会社 | 工業用防カビ組成物 |
JPH10158110A (ja) * | 1996-11-29 | 1998-06-16 | Mitsui Chem Inc | 防菌防黴剤組成物 |
JP3910672B2 (ja) * | 1996-12-20 | 2007-04-25 | 日本エンバイロケミカルズ株式会社 | 安定化された工業用防カビ剤 |
DE19722858B4 (de) * | 1997-05-23 | 2004-01-29 | Schülke & Mayr GmbH | Zusammensetzungen auf der Basis von Iodpropinyl- und Formaldehyd-Depot-Verbindungen und deren Verwendung als Konservierungsmittel |
JPH1121205A (ja) * | 1997-07-03 | 1999-01-26 | Mitsui Chem Inc | 塩化ビニル樹脂成形用組成物 |
EP0900525A1 (de) * | 1997-08-20 | 1999-03-10 | Thor Chemie Gmbh | Synergistische Biozidzusammensetzung |
GB9907269D0 (en) * | 1999-03-30 | 1999-05-26 | Zeneca Ltd | Aqueous fungicide dispersion |
-
2002
- 2002-12-06 WO PCT/US2002/038797 patent/WO2003049543A1/en active Application Filing
- 2002-12-06 US US10/313,420 patent/US6616740B2/en not_active Expired - Lifetime
- 2002-12-06 AU AU2002359604A patent/AU2002359604B2/en not_active Expired
- 2002-12-06 EP EP02794152.5A patent/EP1460899B1/en not_active Expired - Lifetime
- 2002-12-06 KR KR10-2004-7008949A patent/KR20040073475A/ko active Search and Examination
- 2002-12-06 CA CA2469449A patent/CA2469449C/en not_active Expired - Lifetime
- 2002-12-06 JP JP2003550598A patent/JP5226171B2/ja not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012057008A (ja) * | 2010-09-07 | 2012-03-22 | Asahi Organic Chemicals Industry Co Ltd | ポリウレタンフォーム用発泡性組成物並びにポリウレタンフォーム材 |
Also Published As
Publication number | Publication date |
---|---|
KR20040073475A (ko) | 2004-08-19 |
US20030109598A1 (en) | 2003-06-12 |
US6616740B2 (en) | 2003-09-09 |
AU2002359604B2 (en) | 2008-12-11 |
AU2002359604A1 (en) | 2003-06-23 |
WO2003049543A1 (en) | 2003-06-19 |
CA2469449A1 (en) | 2003-06-19 |
EP1460899A1 (en) | 2004-09-29 |
JP5226171B2 (ja) | 2013-07-03 |
CA2469449C (en) | 2011-03-15 |
EP1460899A4 (en) | 2005-01-19 |
EP1460899B1 (en) | 2014-04-16 |
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