CA2700043C - Waterbased dimerized rosins and the process to make them - Google Patents
Waterbased dimerized rosins and the process to make them Download PDFInfo
- Publication number
- CA2700043C CA2700043C CA 2700043 CA2700043A CA2700043C CA 2700043 C CA2700043 C CA 2700043C CA 2700043 CA2700043 CA 2700043 CA 2700043 A CA2700043 A CA 2700043A CA 2700043 C CA2700043 C CA 2700043C
- Authority
- CA
- Canada
- Prior art keywords
- rosin
- sulfonic acid
- catalyst
- dimerized rosin
- acid
- 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
- 238000000034 method Methods 0.000 title claims abstract description 33
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims abstract description 44
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims abstract description 44
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000011347 resin Substances 0.000 claims abstract description 15
- 229920005989 resin Polymers 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 6
- 239000000853 adhesive Substances 0.000 claims abstract description 5
- 230000001070 adhesive effect Effects 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims description 26
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 3
- WNKQDGLSQUASME-UHFFFAOYSA-N 4-sulfophthalic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1C(O)=O WNKQDGLSQUASME-UHFFFAOYSA-N 0.000 claims description 3
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 3
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 claims description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 150000001447 alkali salts Chemical class 0.000 claims 2
- UAZLASMTBCLJKO-UHFFFAOYSA-N 2-decylbenzenesulfonic acid Chemical compound CCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O UAZLASMTBCLJKO-UHFFFAOYSA-N 0.000 claims 1
- XATFRRKBXKIIRM-UHFFFAOYSA-N 2-heptylbenzenesulfonic acid Chemical compound CCCCCCCC1=CC=CC=C1S(O)(=O)=O XATFRRKBXKIIRM-UHFFFAOYSA-N 0.000 claims 1
- SYSFRXFRWRDPIJ-UHFFFAOYSA-N 2-hexylbenzenesulfonic acid Chemical compound CCCCCCC1=CC=CC=C1S(O)(=O)=O SYSFRXFRWRDPIJ-UHFFFAOYSA-N 0.000 claims 1
- QWHHBVWZZLQUIH-UHFFFAOYSA-N 2-octylbenzenesulfonic acid Chemical compound CCCCCCCCC1=CC=CC=C1S(O)(=O)=O QWHHBVWZZLQUIH-UHFFFAOYSA-N 0.000 claims 1
- VBVVNLPJLRAFAI-UHFFFAOYSA-N 2-pentylbenzenesulfonic acid Chemical compound CCCCCC1=CC=CC=C1S(O)(=O)=O VBVVNLPJLRAFAI-UHFFFAOYSA-N 0.000 claims 1
- WPTFZDRBJGXAMT-UHFFFAOYSA-N 4-nonylbenzenesulfonic acid Chemical compound CCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 WPTFZDRBJGXAMT-UHFFFAOYSA-N 0.000 claims 1
- CARJPEPCULYFFP-UHFFFAOYSA-N 5-Sulfo-1,3-benzenedicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 CARJPEPCULYFFP-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 238000006471 dimerization reaction Methods 0.000 abstract description 4
- 239000003377 acid catalyst Substances 0.000 abstract description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000004945 emulsification Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229960004418 trolamine Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RHLPAVIBWYPLRV-UHFFFAOYSA-N 2-hydroxy-4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1O RHLPAVIBWYPLRV-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
- C08L93/04—Rosin
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/08—Printing inks based on natural resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J193/00—Adhesives based on natural resins; Adhesives based on derivatives thereof
- C09J193/04—Rosin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20070075826 EP2039732A1 (en) | 2007-09-20 | 2007-09-20 | Waterbased dimerized rosins and the process to make them |
| EP07075826.3 | 2007-09-20 | ||
| PCT/EP2008/007463 WO2009036920A1 (en) | 2007-09-20 | 2008-09-11 | Waterbased dimerized rosins and the process to make them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2700043A1 CA2700043A1 (en) | 2008-09-20 |
| CA2700043C true CA2700043C (en) | 2013-11-26 |
Family
ID=38924292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2700043 Active CA2700043C (en) | 2007-09-20 | 2008-09-11 | Waterbased dimerized rosins and the process to make them |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US8557954B2 (OSRAM) |
| EP (3) | EP2039732A1 (OSRAM) |
| JP (1) | JP5667443B2 (OSRAM) |
| KR (1) | KR20100065331A (OSRAM) |
| CN (1) | CN101802115A (OSRAM) |
| AR (1) | AR068245A1 (OSRAM) |
| AU (1) | AU2008300927B2 (OSRAM) |
| BR (1) | BRPI0816834B1 (OSRAM) |
| CA (1) | CA2700043C (OSRAM) |
| ES (2) | ES2434826T3 (OSRAM) |
| PL (2) | PL2570464T3 (OSRAM) |
| PT (2) | PT2570464T (OSRAM) |
| TW (1) | TWI399418B (OSRAM) |
| WO (1) | WO2009036920A1 (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2039732A1 (en) * | 2007-09-20 | 2009-03-25 | Hexion Specialty Chemicals Research Belgium S.A. | Waterbased dimerized rosins and the process to make them |
| EP3838998B1 (en) * | 2019-12-19 | 2025-08-06 | Kraton Polymers Research B.V. | Biorenewable hydrocarbon compositions and their uses |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2136525A (en) | 1938-11-15 | Method fob the polymerization of | ||
| GB337733A (en) * | 1929-04-24 | 1930-10-24 | Laszlo Auer | Improvements in and relating to the modification of the physical properties of resins |
| US2011673A (en) * | 1931-04-04 | 1935-08-20 | Ig Farbenindustrie Ag | Process for the manufacture of new conversion products from natural resins and esters thereof |
| US1975211A (en) * | 1931-09-16 | 1934-10-02 | Hercules Powder Co Ltd | Drying oil and method of producing it |
| FR798644A (fr) | 1935-01-24 | 1936-05-22 | Ig Farbenindustrie Ag | Dispositif pour le développement à la lumière du jour des films dentaires radiographiques |
| US2251806A (en) | 1939-04-26 | 1941-08-05 | Ellis Foster Co | Resinous reaction product and process therefor |
| US2288659A (en) * | 1940-04-10 | 1942-07-07 | Hercules Powder Co Ltd | Method for polymerization of rosin |
| US2307641A (en) | 1940-06-12 | 1943-01-05 | Hercules Powder Co Ltd | Polymerization of rosin and rosin esters |
| US2302632A (en) * | 1940-06-14 | 1942-11-17 | Hercules Powder Co Ltd | Polymerization of rosin and rosin esters |
| US2328681A (en) | 1940-06-21 | 1943-09-07 | Hercules Powder Co Ltd | Polymerization of rosin and rosin esters |
| US2341239A (en) * | 1940-12-28 | 1944-02-08 | Colgate Palmolive Peet Co | Polymerization process |
| US2329566A (en) * | 1941-03-01 | 1943-09-14 | Hercules Powder Co Ltd | Method of refining polymerized rosin and polymerized rosin esters |
| US2375618A (en) | 1942-06-30 | 1945-05-08 | Hercules Powder Co Ltd | Method for polymerizing rosin |
| US2340696A (en) * | 1942-09-28 | 1944-02-01 | Hercules Powder Co Ltd | Method of purification of polymerized rosins and rosin esters |
| US2419185A (en) * | 1945-06-20 | 1947-04-15 | Reichhold Chemicals Inc | Polymerization of rosin |
| US2492146A (en) | 1946-02-23 | 1949-12-27 | Glidden Co | Process for refining polymerized rosin |
| US2532120A (en) | 1946-05-21 | 1950-11-28 | Hercules Powder Co Ltd | Condensates of rosin with unsaturated carbocyclic compounds |
| US2515218A (en) | 1946-09-21 | 1950-07-18 | Glidden Co | Polymerization of rosin using activated earths |
| US3954690A (en) * | 1967-11-17 | 1976-05-04 | Hoechst Aktiengesellschaft | Removal of sulfuric acid compounds |
| US3891612A (en) * | 1973-03-05 | 1975-06-24 | Us Agriculture | Polymerized rosin product and process for the production of same |
| GB1474441A (en) * | 1973-08-06 | 1977-05-25 | Monsanto Co | Dispersed rosin |
| IT1017918B (it) * | 1973-08-06 | 1977-08-10 | Monsanto Co | Dispersione stabile di colofonia e procedimento per la sua preparazio ne e utilizzazione |
| JPS5250353A (en) * | 1975-10-21 | 1977-04-22 | Arakawa Chem Ind Co Ltd | Aqueous emulsions of rosin substances |
| AU504229B2 (en) * | 1975-11-17 | 1979-10-04 | A.C. Hatrick Chemicals Pty. Ltd. | Aqueous disperse of fortified rosin |
| US4105462A (en) | 1977-02-10 | 1978-08-08 | Westvaco Corporation | Non-crystallizing rosin |
| US4172070A (en) | 1978-03-27 | 1979-10-23 | Arizona Chemical Company | Oxygen-stable rosin-primary polyhydric aliphatic alcohol esters and a method for preparing the same utilizing arylsulfonic acid catalysis |
| US4263182A (en) * | 1979-09-06 | 1981-04-21 | Hercules Incorporated | Stable dispersions of fortified rosin |
| US4374673A (en) * | 1980-12-31 | 1983-02-22 | Hercules Incorporated | Stable dispersions of fortified rosin |
| US4339377A (en) | 1981-09-08 | 1982-07-13 | Union Camp Corporation | Method of polymerizing rosin |
| US4414146A (en) | 1982-05-05 | 1983-11-08 | Union Camp Corporation | Method of polymerizing rosin |
| JPS608394A (ja) * | 1983-06-28 | 1985-01-17 | Nikka Chem Ind Co Ltd | ピツチの水中分散剤及びピツチ組成物 |
| US4536333A (en) | 1984-08-22 | 1985-08-20 | Union Camp Corporation | Method of polymerizing rosin |
| US5021548A (en) * | 1990-01-22 | 1991-06-04 | Hercules Incorporated | Sodium hydroxymethane sulfonate to improve the color stability of rosin resins |
| SE506467C2 (sv) * | 1991-06-28 | 1997-12-22 | Eka Chemicals Ab | Förfarande för framställning av stabiliserad kolofonium och dess användning som klibbgivarharts i bindemedel |
| BR9707265A (pt) * | 1996-02-02 | 1999-04-13 | Hercules Inc | Sistema emulsificante para agentes de engomação de colof nia |
| EP1035188A1 (en) * | 1996-04-15 | 2000-09-13 | Hercules Incorporated | Viscosity modifier for hot-melt adhesives |
| GB9610955D0 (en) * | 1996-05-24 | 1996-07-31 | Hercules Inc | Sizing composition |
| JP3922470B2 (ja) * | 1996-06-18 | 2007-05-30 | 荒川化学工業株式会社 | 淡色ロジン金属塩の製造方法 |
| GB9721188D0 (en) * | 1997-10-08 | 1997-12-03 | Raisio Chemicals Uk Limited | Rosin emulsion |
| DE10023286A1 (de) * | 2000-05-12 | 2001-11-15 | Merck Patent Gmbh | Pigmentpräparation mit modifizierten Kolophoniumharzen |
| JP2002003793A (ja) * | 2000-06-23 | 2002-01-09 | Toho Chem Ind Co Ltd | ロジンフレークの製造方法 |
| JP2002226790A (ja) * | 2001-02-06 | 2002-08-14 | Arakawa Chem Ind Co Ltd | 重合ロジンの製造法 |
| CN100368491C (zh) | 2001-11-09 | 2008-02-13 | 太阳化学公司 | 低粘性可水洗的石印印刷油墨 |
| US20030229178A1 (en) * | 2002-05-13 | 2003-12-11 | Locko George A. | Phenolic-modified rosin terpene resin |
| US6849681B2 (en) * | 2002-07-10 | 2005-02-01 | Meadwestvaco Corporation | Carboxylic acid-modified vinylic polymeric compositions |
| US6878791B2 (en) * | 2003-05-09 | 2005-04-12 | Ppg Industries Ohio, Inc. | Aminoplast crosslinkers derived from tall oil rosin powder coating compositions containing such crosslinkers |
| US20050054801A1 (en) * | 2003-09-04 | 2005-03-10 | Arizona Chemical Company | Resins and adhesive formulations therewith |
| US9023929B2 (en) * | 2004-02-13 | 2015-05-05 | Lawter, Inc. | Tackifier dispersion |
| JP2006037036A (ja) * | 2004-07-30 | 2006-02-09 | Toyo Ink Mfg Co Ltd | 多量体樹脂酸組成物の製造方法 |
| JP5028767B2 (ja) * | 2005-08-24 | 2012-09-19 | 荒川化学工業株式会社 | 粘着付与樹脂エマルジョン、その製造方法および水性粘接着剤組成物 |
| JP4561622B2 (ja) * | 2005-12-20 | 2010-10-13 | 富士ゼロックス株式会社 | 静電荷像現像トナー用樹脂粒子分散液及びその製造方法、静電荷像現像トナー及びその製造方法、静電荷像現像剤、並びに、画像形成方法 |
| US20070254985A1 (en) * | 2006-04-21 | 2007-11-01 | Maas Joost H | Resin dispersions with low surfactant concentrations |
| EP2039732A1 (en) * | 2007-09-20 | 2009-03-25 | Hexion Specialty Chemicals Research Belgium S.A. | Waterbased dimerized rosins and the process to make them |
-
2007
- 2007-09-20 EP EP20070075826 patent/EP2039732A1/en not_active Withdrawn
-
2008
- 2008-09-02 TW TW97133645A patent/TWI399418B/zh active
- 2008-09-11 ES ES08802024T patent/ES2434826T3/es active Active
- 2008-09-11 CN CN200880107899A patent/CN101802115A/zh active Pending
- 2008-09-11 CA CA 2700043 patent/CA2700043C/en active Active
- 2008-09-11 PL PL12184851T patent/PL2570464T3/pl unknown
- 2008-09-11 KR KR20107006101A patent/KR20100065331A/ko not_active Ceased
- 2008-09-11 AU AU2008300927A patent/AU2008300927B2/en active Active
- 2008-09-11 US US12/674,747 patent/US8557954B2/en active Active
- 2008-09-11 JP JP2010525235A patent/JP5667443B2/ja active Active
- 2008-09-11 BR BRPI0816834-2A patent/BRPI0816834B1/pt active IP Right Grant
- 2008-09-11 EP EP20080802024 patent/EP2190940B1/en active Active
- 2008-09-11 EP EP12184851.9A patent/EP2570464B1/en not_active Not-in-force
- 2008-09-11 PL PL08802024T patent/PL2190940T3/pl unknown
- 2008-09-11 PT PT121848519T patent/PT2570464T/pt unknown
- 2008-09-11 WO PCT/EP2008/007463 patent/WO2009036920A1/en not_active Ceased
- 2008-09-11 ES ES12184851.9T patent/ES2637630T3/es active Active
- 2008-09-11 PT PT08802024T patent/PT2190940E/pt unknown
- 2008-09-19 AR ARP080104104 patent/AR068245A1/es active IP Right Grant
-
2013
- 2013-08-23 US US13/974,996 patent/US9012601B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| PL2190940T3 (pl) | 2014-01-31 |
| BRPI0816834A2 (pt) | 2015-03-17 |
| US20130345390A1 (en) | 2013-12-26 |
| EP2039732A1 (en) | 2009-03-25 |
| CA2700043A1 (en) | 2008-09-20 |
| US20110092667A1 (en) | 2011-04-21 |
| WO2009036920A1 (en) | 2009-03-26 |
| CN101802115A (zh) | 2010-08-11 |
| US9012601B2 (en) | 2015-04-21 |
| EP2570464A1 (en) | 2013-03-20 |
| ES2637630T3 (es) | 2017-10-13 |
| KR20100065331A (ko) | 2010-06-16 |
| AU2008300927A1 (en) | 2009-03-26 |
| EP2570464B1 (en) | 2017-05-17 |
| PL2570464T3 (pl) | 2017-12-29 |
| PT2570464T (pt) | 2017-07-20 |
| TW200930778A (en) | 2009-07-16 |
| AR068245A1 (es) | 2009-11-11 |
| AU2008300927B2 (en) | 2012-02-09 |
| EP2190940A1 (en) | 2010-06-02 |
| EP2190940B1 (en) | 2013-08-28 |
| US8557954B2 (en) | 2013-10-15 |
| PT2190940E (pt) | 2013-10-14 |
| JP5667443B2 (ja) | 2015-02-12 |
| BRPI0816834B1 (pt) | 2018-06-12 |
| JP2010539305A (ja) | 2010-12-16 |
| ES2434826T3 (es) | 2013-12-17 |
| TWI399418B (zh) | 2013-06-21 |
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