CA2641210A1 - Thermoplastic resins containing pbt units, having reduced organic carbon emissions - Google Patents
Thermoplastic resins containing pbt units, having reduced organic carbon emissions Download PDFInfo
- Publication number
- CA2641210A1 CA2641210A1 CA002641210A CA2641210A CA2641210A1 CA 2641210 A1 CA2641210 A1 CA 2641210A1 CA 002641210 A CA002641210 A CA 002641210A CA 2641210 A CA2641210 A CA 2641210A CA 2641210 A1 CA2641210 A1 CA 2641210A1
- Authority
- CA
- Canada
- Prior art keywords
- pbt
- resin
- compound
- titanium catalyst
- optionally substituted
- 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.)
- Abandoned
Links
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title abstract description 11
- 229910052799 carbon Inorganic materials 0.000 title abstract description 11
- 229920005992 thermoplastic resin Polymers 0.000 title description 6
- 229920005989 resin Polymers 0.000 claims abstract description 76
- 239000011347 resin Substances 0.000 claims abstract description 76
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 239000003054 catalyst Substances 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 42
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 71
- 239000010936 titanium Substances 0.000 claims description 58
- 229910052719 titanium Inorganic materials 0.000 claims description 50
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 49
- -1 polybutylene terephthalate Polymers 0.000 claims description 46
- 238000010943 off-gassing Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 11
- 229920001971 elastomer Polymers 0.000 claims description 9
- 239000000806 elastomer Substances 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 7
- 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 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- MLCHBQKMVKNBOV-UHFFFAOYSA-M dioxido(phenyl)phosphanium Chemical compound [O-]P(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-M 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 159000000013 aluminium salts Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- MORLYCDUFHDZKO-UHFFFAOYSA-N 3-[hydroxy(phenyl)phosphoryl]propanoic acid Chemical compound OC(=O)CCP(O)(=O)C1=CC=CC=C1 MORLYCDUFHDZKO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000329 aluminium sulfate Inorganic materials 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- KTLIMPGQZDZPSB-UHFFFAOYSA-N diethylphosphinic acid Chemical compound CCP(O)(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-N 0.000 claims description 2
- GTTBQSNGUYHPNK-UHFFFAOYSA-N hydroxymethylphosphonic acid Chemical compound OCP(O)(O)=O GTTBQSNGUYHPNK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 2
- ZHROMWXOTYBIMF-UHFFFAOYSA-M sodium;1,3,7,9-tetratert-butyl-11-oxido-5h-benzo[d][1,3,2]benzodioxaphosphocine 11-oxide Chemical compound [Na+].C1C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP([O-])(=O)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C ZHROMWXOTYBIMF-UHFFFAOYSA-M 0.000 claims 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910001380 potassium hypophosphite Inorganic materials 0.000 claims 1
- CRGPNLUFHHUKCM-UHFFFAOYSA-M potassium phosphinate Chemical compound [K+].[O-]P=O CRGPNLUFHHUKCM-UHFFFAOYSA-M 0.000 claims 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- 238000000465 moulding Methods 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000000523 sample Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 5
- 229920010930 Hytrel® 5556 Polymers 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000007493 shaping process Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- GGQHNQQPLWRNHD-UHFFFAOYSA-N 1,3,7,9-tetratert-butyl-11-hydroxy-5h-benzo[d][1,3,2]benzodioxaphosphocine 11-oxide Chemical compound C1C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP(O)(=O)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C GGQHNQQPLWRNHD-UHFFFAOYSA-N 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
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002124 flame ionisation detection Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- GRWPYGBKJYICOO-UHFFFAOYSA-N 2-methylpropan-2-olate;titanium(4+) Chemical compound [Ti+4].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] GRWPYGBKJYICOO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KVCWSJZUKMSPLM-UHFFFAOYSA-N O.O[PH2]=O Chemical compound O.O[PH2]=O KVCWSJZUKMSPLM-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical group OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XSAOTYCWGCRGCP-UHFFFAOYSA-K aluminum;diethylphosphinate Chemical compound [Al+3].CCP([O-])(=O)CC.CCP([O-])(=O)CC.CCP([O-])(=O)CC XSAOTYCWGCRGCP-UHFFFAOYSA-K 0.000 description 1
- 238000001636 atomic emission spectroscopy Methods 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 108010011222 cyclo(Arg-Pro) Proteins 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 238000004876 x-ray fluorescence 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- 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
- C08K5/49—Phosphorus-containing compounds
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78542706P | 2006-03-24 | 2006-03-24 | |
| US60/785,427 | 2006-03-24 | ||
| PCT/US2007/006940 WO2007111890A2 (en) | 2006-03-24 | 2007-03-20 | Thermoplastic resins containing pbt units, having reduced organic carbon emissions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2641210A1 true CA2641210A1 (en) | 2007-10-04 |
Family
ID=38440254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002641210A Abandoned CA2641210A1 (en) | 2006-03-24 | 2007-03-20 | Thermoplastic resins containing pbt units, having reduced organic carbon emissions |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8148489B2 (enExample) |
| EP (1) | EP1999181B2 (enExample) |
| JP (1) | JP2009531519A (enExample) |
| CA (1) | CA2641210A1 (enExample) |
| WO (1) | WO2007111890A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080006970A1 (en) | 2006-07-10 | 2008-01-10 | General Electric Company | Filtered polyetherimide polymer for use as a high heat fiber material |
| US9416465B2 (en) | 2006-07-14 | 2016-08-16 | Sabic Global Technologies B.V. | Process for making a high heat polymer fiber |
| JP5123013B2 (ja) * | 2008-03-11 | 2013-01-16 | 花王株式会社 | 縮重合系樹脂の製造方法 |
| JP5468815B2 (ja) * | 2009-05-15 | 2014-04-09 | 帝人株式会社 | ポリエステル組成物およびそれを用いたフィルムとその製造方法 |
| JP5969475B2 (ja) * | 2011-07-20 | 2016-08-17 | ウィンテックポリマー株式会社 | 樹脂成形体及び自動車内装部品 |
| JP5932792B2 (ja) * | 2011-07-20 | 2016-06-08 | ウィンテックポリマー株式会社 | 樹脂成形体及び自動車内装部品 |
| HUE037321T2 (hu) | 2013-06-07 | 2018-08-28 | Basf Se | Kis TOC emissziójú poliészter formázó massza |
| EP2816081A1 (de) | 2013-06-17 | 2014-12-24 | Basf Se | Polyesterformmassen mit geringer TOC Emission |
| US10752750B2 (en) | 2014-11-13 | 2020-08-25 | Sabic Global Technologies B.V. | Polyester composition and article prepared therefrom |
| CN107667145B (zh) | 2015-05-26 | 2020-06-30 | Sabic环球技术有限责任公司 | 聚(对苯二甲酸丁二酯)组合物及相关制品 |
| WO2017036653A1 (en) * | 2015-08-28 | 2017-03-09 | Sabic Global Technologies B.V. | Poly(butylene terephthalate) method and associated composition and article |
| CN114174429B (zh) * | 2019-07-29 | 2024-04-19 | 朗盛德国有限责任公司 | 具有低thf含量的聚对苯二甲酸丁二酯 |
| EP4004109B1 (de) | 2019-07-29 | 2024-08-21 | Envalior Deutschland GmbH | Polybutylenterephthalat mit niedrigem thf gehalt |
| JP7325603B2 (ja) | 2019-07-29 | 2023-08-14 | ランクセス・ドイチュランド・ゲーエムベーハー | 低いｔｈｆ含量のポリブチレンテレフタレート |
| WO2024087056A1 (en) * | 2022-10-26 | 2024-05-02 | Du Pont China Holding Company Limited, Shanghai Branch | Polymer composite with low voc emission |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1421972A (en) * | 1973-07-16 | 1976-01-21 | Ici Ltd | Polyester catalysts |
| JPS5921886B2 (ja) * | 1974-10-03 | 1984-05-23 | 帝人株式会社 | ポリエステルブロツク共重合体の製造法 |
| CH594715A5 (enExample) * | 1976-02-26 | 1978-01-31 | Ciba Geigy Ag | |
| JPS5578018A (en) * | 1978-12-06 | 1980-06-12 | Toray Ind Inc | Preparation of polytetramethylene terephthalate |
| JPH06172506A (ja) | 1992-12-03 | 1994-06-21 | Polyplastics Co | 改質ポリブチレンテレフタレート樹脂の製造方法 |
| JP3618429B2 (ja) * | 1995-11-07 | 2005-02-09 | 株式会社クラレ | 熱可塑性重合体組成物 |
| US5789528A (en) * | 1995-12-08 | 1998-08-04 | Akzo Nobel Nv | Process for the preparation of polyesters and copolyesters |
| JPH1030054A (ja) * | 1996-07-12 | 1998-02-03 | Mitsubishi Rayon Co Ltd | ポリエステル系樹脂組成物 |
| JPH10310638A (ja) * | 1997-05-09 | 1998-11-24 | Polyplastics Co | 熱可塑性ポリエステルの製造方法 |
| JP3749601B2 (ja) * | 1997-09-12 | 2006-03-01 | 帝人ファイバー株式会社 | ブロック共重合ポリエステル及びその製造方法 |
| US6489433B2 (en) * | 2001-02-23 | 2002-12-03 | E. I. Du Pont De Nemours And Company | Metal-containing composition and process therewith |
| TWI255821B (en) | 2003-01-22 | 2006-06-01 | Asahi Kasei Chemicals Corp | Polytrimethylene terephthalate resin and method for production thereof |
| JP4788865B2 (ja) * | 2004-10-04 | 2011-10-05 | 東洋紡績株式会社 | マスターバッチ用熱可塑性樹脂組成物およびその成形材料の製造方法およびそれらを用いた熱可塑性樹脂組成物およびその製造方法 |
| DE10359814A1 (de) † | 2003-12-19 | 2005-07-28 | Clariant Gmbh | Dialkylphosphinsäure-Salze |
| JP2005187732A (ja) * | 2003-12-26 | 2005-07-14 | Du Pont Toray Co Ltd | ポリエステルエラストマ樹脂組成物 |
| US20050215425A1 (en) * | 2004-03-26 | 2005-09-29 | Clair Jerry D S | Esterification catalyst and process therewith |
| JP2007182476A (ja) * | 2006-01-05 | 2007-07-19 | Toyobo Co Ltd | ポリエステル樹脂及びそれからなるポリエステル樹脂組成物並びにその用途 |
-
2007
- 2007-03-15 US US11/724,454 patent/US8148489B2/en not_active Expired - Fee Related
- 2007-03-20 WO PCT/US2007/006940 patent/WO2007111890A2/en not_active Ceased
- 2007-03-20 JP JP2009502858A patent/JP2009531519A/ja active Pending
- 2007-03-20 EP EP07753559.9A patent/EP1999181B2/en not_active Ceased
- 2007-03-20 CA CA002641210A patent/CA2641210A1/en not_active Abandoned
-
2012
- 2012-02-27 US US13/405,393 patent/US20120165443A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20070225475A1 (en) | 2007-09-27 |
| JP2009531519A (ja) | 2009-09-03 |
| WO2007111890A3 (en) | 2008-05-15 |
| US8148489B2 (en) | 2012-04-03 |
| EP1999181B1 (en) | 2014-07-16 |
| US20120165443A1 (en) | 2012-06-28 |
| EP1999181A2 (en) | 2008-12-10 |
| WO2007111890A2 (en) | 2007-10-04 |
| EP1999181B2 (en) | 2018-01-17 |
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