ES2651912T3 - Composición adhesiva de resina de poliaminopoliamida-epiclorhidrina (PAE) de bajo peso molecular y proteína - Google Patents
Composición adhesiva de resina de poliaminopoliamida-epiclorhidrina (PAE) de bajo peso molecular y proteína Download PDFInfo
- Publication number
- ES2651912T3 ES2651912T3 ES07811512.8T ES07811512T ES2651912T3 ES 2651912 T3 ES2651912 T3 ES 2651912T3 ES 07811512 T ES07811512 T ES 07811512T ES 2651912 T3 ES2651912 T3 ES 2651912T3
- Authority
- ES
- Spain
- Prior art keywords
- reaction
- resin
- molecular weight
- pae
- epichlorohydrin
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title abstract description 12
- 102000004169 proteins and genes Human genes 0.000 title abstract 2
- 108090000623 proteins and genes Proteins 0.000 title abstract 2
- 229920005989 resin Polymers 0.000 title description 38
- 239000011347 resin Substances 0.000 title description 38
- 239000000853 adhesive Substances 0.000 title description 12
- 230000001070 adhesive effect Effects 0.000 title description 12
- 229920000768 polyamine Polymers 0.000 title 1
- 238000001542 size-exclusion chromatography Methods 0.000 abstract description 11
- 229920000642 polymer Polymers 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 17
- 229920000962 poly(amidoamine) Polymers 0.000 description 15
- 238000010411 cooking Methods 0.000 description 12
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 11
- 235000011037 adipic acid Nutrition 0.000 description 11
- 239000001361 adipic acid Substances 0.000 description 11
- 235000010469 Glycine max Nutrition 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 235000013312 flour Nutrition 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-O azetidin-1-ium Chemical compound C1C[NH2+]C1 HONIICLYMWZJFZ-UHFFFAOYSA-O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Chemical compound [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 description 2
- 229940092597 prolia Drugs 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- SAORNRFCWXEYSW-UHFFFAOYSA-M 1-propylpyridin-1-ium;bromide Chemical compound [Br-].CCC[N+]1=CC=CC=C1 SAORNRFCWXEYSW-UHFFFAOYSA-M 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WCBJENANOLBYPD-UHFFFAOYSA-N n'-(2-aminoethyl)ethane-1,2-diamine;hexanedioic acid Chemical compound NCCNCCN.OC(=O)CCCCC(O)=O WCBJENANOLBYPD-UHFFFAOYSA-N 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000079 presaturation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/005—Lignin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27N—MANUFACTURE BY DRY PROCESSES OF ARTICLES, WITH OR WITHOUT ORGANIC BINDING AGENTS, MADE FROM PARTICLES OR FIBRES CONSISTING OF WOOD OR OTHER LIGNOCELLULOSIC OR LIKE ORGANIC MATERIAL
- B27N3/00—Manufacture of substantially flat articles, e.g. boards, from particles or fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L89/00—Compositions of proteins; Compositions of derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/02—Lignocellulosic material, e.g. wood, straw or bagasse
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
- Y10T428/31779—Next to cellulosic
- Y10T428/31783—Paper or wood
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Manufacturing & Machinery (AREA)
- Forests & Forestry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyamides (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83974506P | 2006-08-24 | 2006-08-24 | |
| US839745P | 2006-08-24 | ||
| PCT/US2007/018666 WO2008024444A2 (en) | 2006-08-24 | 2007-08-23 | Adhesive composition of low molecular weight polyaminopolyamide-epichlorohydrin (pae) resin and protein |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2651912T3 true ES2651912T3 (es) | 2018-01-30 |
Family
ID=38871563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07811512.8T Active ES2651912T3 (es) | 2006-08-24 | 2007-08-23 | Composición adhesiva de resina de poliaminopoliamida-epiclorhidrina (PAE) de bajo peso molecular y proteína |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20080050602A1 (https=) |
| EP (1) | EP2054461B1 (https=) |
| JP (1) | JP5275991B2 (https=) |
| KR (1) | KR101391474B1 (https=) |
| CN (1) | CN101558101B (https=) |
| AU (1) | AU2007288209B2 (https=) |
| BR (1) | BRPI0716586B1 (https=) |
| CA (1) | CA2661466C (https=) |
| ES (1) | ES2651912T3 (https=) |
| MX (1) | MX2009001899A (https=) |
| MY (1) | MY150700A (https=) |
| RU (1) | RU2448126C2 (https=) |
| TW (1) | TWI411645B (https=) |
| WO (1) | WO2008024444A2 (https=) |
| ZA (1) | ZA200902057B (https=) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7678879B2 (en) * | 2006-11-01 | 2010-03-16 | Designer Molecules, Inc. | Adhesive composition of phenol-functional polyamides |
| CA2701918C (en) * | 2007-10-09 | 2014-08-05 | Hercules Incorporated | Crosslinkercontaining adhesive compositions |
| JP5446015B2 (ja) * | 2008-04-08 | 2014-03-19 | エルジー・ケム・リミテッド | 接着剤組成物及びこれを用いた光学フィルム |
| US20100040832A1 (en) * | 2008-08-13 | 2010-02-18 | Saint-Gobain Technical Fabrics America, Inc. | Formaldehyde free woven and non-woven fabrics having improved hot wet tensile strength and binder formulations for same |
| EP2334748B1 (en) * | 2008-09-08 | 2019-06-05 | Solenis Technologies Cayman, L.P. | Protein/cationic polymer compositions having reduced viscosity |
| US20100197185A1 (en) * | 2009-01-30 | 2010-08-05 | Saint-Gobain Technical Fabrics America, Inc. | Low and ultra-low formaldehyde emission binders for non-woven glass mat |
| US8623931B2 (en) * | 2009-03-06 | 2014-01-07 | Biopolymer Technologies, Ltd. | Protein-containing foams, manufacture and use thereof |
| RU2558365C2 (ru) | 2009-03-06 | 2015-08-10 | Байополимер Текнолоджиз, Лтд. | Эмульсии и клеи, содержащие белок, их получение и применение |
| EP2456828A1 (en) | 2009-07-20 | 2012-05-30 | Akzo Nobel Coatings International B.V. | Adhesive system and method of producing a wood based product |
| US20110223364A1 (en) * | 2009-10-09 | 2011-09-15 | Hawkins Christopher M | Insulative products having bio-based binders |
| ES2530624T3 (es) * | 2010-02-04 | 2015-03-04 | Solenis Technologies Cayman Lp | Composiciones de adhesivo |
| CA2797728C (en) | 2010-05-26 | 2018-10-02 | Hercules Incorporated | Protein adhesive formulations with amine-epichlorohydrin and isocyanate additives |
| EP2576661B1 (en) | 2010-06-07 | 2016-12-14 | Evertree | Protein-containing adhesives, and manufacture and use thereof |
| US8470124B1 (en) | 2010-08-17 | 2013-06-25 | Columbia Forest Products, Inc. | Cold pressing process for polyamide epichlorohydrin (PAE) based wood adhesive |
| WO2012076566A2 (en) | 2010-12-10 | 2012-06-14 | Akzo Nobel Coatings International B.V. | Aqueous composition |
| WO2013003675A2 (en) * | 2011-06-30 | 2013-01-03 | Hercules Incorporated | Adhesive additive |
| HUE032642T2 (en) | 2011-09-09 | 2017-10-30 | Evertree | Protein-based adhesives, their production and use |
| CA3075143C (en) | 2011-09-09 | 2023-03-28 | Evertree | Protein-containing adhesives, and manufacture and use thereof |
| PT2761083T (pt) | 2011-09-30 | 2017-08-24 | Kemira Oyj | Papel e métodos para produzir papel |
| EP2666758A1 (en) | 2012-05-25 | 2013-11-27 | Saint-Gobain Placo SAS | Gypsum-based building products and method for the manufacure thereof |
| EP2880116B1 (en) | 2012-07-30 | 2020-02-05 | Evertree | Protein adhesives containing an anhydride, carboxylic acid, and/or carboxylate salt compound and their use |
| WO2014070036A1 (en) * | 2012-11-02 | 2014-05-08 | Gridnev Alexei Alexeevich | Lignin composite material |
| BE1021591B1 (nl) | 2013-04-05 | 2015-12-16 | Unilin Bvba | Fabricage van plaatmateriaal en daartoe geschikte biolijm |
| DE102014103924A1 (de) | 2013-04-05 | 2014-10-09 | Fischerwerke Gmbh & Co. Kg | Feste biogene Füllstoffe in Verklebungsmitteln für die Befestigungstechnik |
| CN103740326A (zh) * | 2014-01-13 | 2014-04-23 | 阎肖华 | 一种蛋白基木材胶粘剂及其制备方法 |
| CN104845549B (zh) | 2014-02-18 | 2019-07-12 | 财团法人工业技术研究院 | 木材粘着剂及应用其的木材粘着方法和木材接合结构 |
| US9492961B2 (en) * | 2014-08-01 | 2016-11-15 | Usg Interiors, Llc | Acoustic ceiling tiles with anti-sagging properties and methods of making same |
| TWI564356B (zh) | 2015-09-18 | 2017-01-01 | 財團法人工業技術研究院 | 木材黏著劑 |
| US10300638B2 (en) * | 2016-03-01 | 2019-05-28 | Solenis Technologies, L.P. | Process for improved composite board manufacture |
| EP3452548B1 (en) | 2016-05-05 | 2024-10-16 | Cargill, Incorporated | Wood adhesive compositions comprising proteins and poly (glycidyl ether), and uses thereof |
| CN107365566B (zh) * | 2016-05-12 | 2020-08-28 | 中国林业科学研究院木材工业研究所 | 一种无醛改性豆基蛋白胶黏剂及其制造方法 |
| CN109135662A (zh) * | 2017-06-15 | 2019-01-04 | 山东绿点环保材料有限公司 | 大豆胶及其制备方法以及利用大豆胶生产轻质板的方法 |
| CA3076409A1 (en) * | 2017-09-20 | 2019-03-28 | Sestec Innovations Sp. Z O.O. | Binder for cellulose-containing materials |
| CN110067146A (zh) * | 2019-05-09 | 2019-07-30 | 南京林业大学 | 一种添加复配木素抄造高强度纸的方法 |
| CN110894422B (zh) * | 2019-12-11 | 2021-04-20 | 德华兔宝宝装饰新材股份有限公司 | 一种豆粕胶黏剂及其制备方法 |
| US12338579B2 (en) | 2020-03-06 | 2025-06-24 | Kemira Oyj | Composition and method for manufacture of paper, board or the like |
| CN111732928A (zh) * | 2020-07-10 | 2020-10-02 | 宁波中科朝露新材料有限公司 | 一种采用饲料用大豆粕制备大豆基胶黏剂的方法及应用 |
| CN112322243B (zh) * | 2020-11-16 | 2022-05-13 | 东北林业大学 | 防水级聚酰胺基胶粘剂及其制备方法 |
| EP4467626A1 (en) | 2023-05-23 | 2024-11-27 | Evertree | Adhesive composition for bonding glass fibers |
| EP4467625A1 (en) | 2023-05-23 | 2024-11-27 | Evertree | Adhesive composition for bonding stone fibers |
| CN116574390B (zh) * | 2023-06-14 | 2024-05-03 | 东北林业大学 | 一种无机杂化增强的秸秆基生物质复合材料及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US2926154A (en) * | 1957-09-05 | 1960-02-23 | Hercules Powder Co Ltd | Cationic thermosetting polyamide-epichlorohydrin resins and process of making same |
| NL110447C (https=) * | 1957-09-05 | |||
| US3494775A (en) * | 1966-06-10 | 1970-02-10 | American Cyanamid Co | Protein adhesive compositions containing an amine-epichlorohydrin condensate latent insolubilizing agent |
| US4172887A (en) * | 1973-11-30 | 1979-10-30 | L'oreal | Hair conditioning compositions containing crosslinked polyaminopolyamides |
| LU76955A1 (https=) * | 1977-03-15 | 1978-10-18 | ||
| JPS54159496A (en) * | 1978-06-07 | 1979-12-17 | Sumitomo Chem Co Ltd | Preparation of aqueous solution of cationic thermosetting resin |
| US5763509A (en) * | 1985-03-18 | 1998-06-09 | The Board Of Regents Of The University Of Nebraska | Binder containing plant protein and densified refuse fuel cubes made using same and methods of making them |
| US5374670A (en) * | 1985-03-18 | 1994-12-20 | The Board Of Regents Of The University Of Nebraska | Binders, method of making and using binders and structures made using binders |
| US4853431A (en) * | 1987-12-07 | 1989-08-01 | Georgia-Pacific Resins, Inc. | Method for stabilizing aqueous solutions of cationic thermosetting polyamide-epichlorohydrin resins |
| DE3822490A1 (de) * | 1988-07-02 | 1990-01-04 | Hoechst Ag | Waessrige loesungen von polyamidoamin-epichlorhyrin-harzen, verfahren zu ihrer herstellung und ihre verwendung |
| JP2969636B2 (ja) * | 1988-12-23 | 1999-11-02 | 住友化学工業株式会社 | 陽イオン性熱硬化性樹脂水溶液の製造方法 |
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| JP2002201267A (ja) * | 2001-01-05 | 2002-07-19 | Sumitomo Chem Co Ltd | 水性ポリアミドアミン−エピクロロヒドリン樹脂の製造方法 |
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| US7252735B2 (en) * | 2002-05-13 | 2007-08-07 | State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon State University | Formaldehyde-free lignocellulosic adhesives and composites made from the adhesives |
| CN100588687C (zh) * | 2002-07-19 | 2010-02-10 | 佛蒙特大学及州农业学院 | 木质涂饰剂及其生产方法 |
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| US7081512B2 (en) * | 2003-05-21 | 2006-07-25 | Hercules Incorporated | Treatment of resins to lower levels of CPD-producing species and improve gelation stability |
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| CA2458159A1 (en) * | 2004-01-22 | 2005-07-22 | The State Of Oregon Acting By And Through The State Board Of Higher Educ Ation On Behalf Of Oregon State University | Formaldehyde-free adhesives and lignocellulosic composites made from the adhesives |
| US7736559B2 (en) * | 2004-05-20 | 2010-06-15 | Georgia-Pacific Chemicals Llc | Binding wood using a thermosetting adhesive composition comprising a protein-based component and a polymeric quaternary amine cure accelerant |
| US20050261404A1 (en) * | 2004-05-20 | 2005-11-24 | Georgia-Pacific Resins, Inc. | Thermosetting adhesive compositions comprising a protein-based component and a polymeric quaternary amine cure accelerant |
-
2007
- 2007-08-23 WO PCT/US2007/018666 patent/WO2008024444A2/en not_active Ceased
- 2007-08-23 MY MYPI20090701A patent/MY150700A/en unknown
- 2007-08-23 KR KR1020097005902A patent/KR101391474B1/ko not_active Expired - Fee Related
- 2007-08-23 EP EP07811512.8A patent/EP2054461B1/en active Active
- 2007-08-23 AU AU2007288209A patent/AU2007288209B2/en not_active Ceased
- 2007-08-23 RU RU2009110251/04A patent/RU2448126C2/ru not_active IP Right Cessation
- 2007-08-23 ES ES07811512.8T patent/ES2651912T3/es active Active
- 2007-08-23 CN CN2007800395377A patent/CN101558101B/zh not_active Expired - Fee Related
- 2007-08-23 US US11/895,122 patent/US20080050602A1/en not_active Abandoned
- 2007-08-23 MX MX2009001899A patent/MX2009001899A/es active IP Right Grant
- 2007-08-23 BR BRPI0716586-2A patent/BRPI0716586B1/pt not_active IP Right Cessation
- 2007-08-23 JP JP2009525634A patent/JP5275991B2/ja not_active Expired - Fee Related
- 2007-08-23 CA CA 2661466 patent/CA2661466C/en active Active
- 2007-08-24 TW TW96131517A patent/TWI411645B/zh not_active IP Right Cessation
-
2009
- 2009-03-24 ZA ZA200902057A patent/ZA200902057B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0716586B1 (pt) | 2019-04-09 |
| EP2054461B1 (en) | 2017-08-23 |
| BRPI0716586A2 (pt) | 2013-10-01 |
| WO2008024444A2 (en) | 2008-02-28 |
| US20080050602A1 (en) | 2008-02-28 |
| CA2661466A1 (en) | 2008-02-28 |
| AU2007288209B2 (en) | 2012-06-07 |
| RU2448126C2 (ru) | 2012-04-20 |
| JP5275991B2 (ja) | 2013-08-28 |
| JP2010501670A (ja) | 2010-01-21 |
| ZA200902057B (en) | 2010-08-25 |
| CN101558101A (zh) | 2009-10-14 |
| KR101391474B1 (ko) | 2014-05-19 |
| KR20090051768A (ko) | 2009-05-22 |
| EP2054461A2 (en) | 2009-05-06 |
| TWI411645B (zh) | 2013-10-11 |
| MX2009001899A (es) | 2009-03-25 |
| MY150700A (en) | 2014-02-28 |
| TW200827404A (en) | 2008-07-01 |
| RU2009110251A (ru) | 2010-09-27 |
| AU2007288209A1 (en) | 2008-02-28 |
| WO2008024444A3 (en) | 2008-05-02 |
| CN101558101B (zh) | 2013-02-06 |
| CA2661466C (en) | 2014-04-15 |
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