HRP20150985T1 - Postupak proizvodnje polihidroksi-karboksilne kiseline - Google Patents
Postupak proizvodnje polihidroksi-karboksilne kiseline Download PDFInfo
- Publication number
- HRP20150985T1 HRP20150985T1 HRP20150985TT HRP20150985T HRP20150985T1 HR P20150985 T1 HRP20150985 T1 HR P20150985T1 HR P20150985T T HRP20150985T T HR P20150985TT HR P20150985 T HRP20150985 T HR P20150985T HR P20150985 T1 HRP20150985 T1 HR P20150985T1
- Authority
- HR
- Croatia
- Prior art keywords
- lactide
- crystallization
- degassing
- polylactic acid
- impurities
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 14
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 238000002425 crystallisation Methods 0.000 claims 12
- 230000008025 crystallization Effects 0.000 claims 12
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims 12
- 238000007872 degassing Methods 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 6
- 239000012535 impurity Substances 0.000 claims 6
- 229920000747 poly(lactic acid) Polymers 0.000 claims 6
- 239000004626 polylactic acid Substances 0.000 claims 6
- 238000009835 boiling Methods 0.000 claims 4
- 239000007789 gas Substances 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 3
- 238000006116 polymerization reaction Methods 0.000 claims 3
- 238000000746 purification Methods 0.000 claims 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims 3
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000013016 damping Methods 0.000 claims 1
- 238000006471 dimerization reaction Methods 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- 238000007142 ring opening reaction Methods 0.000 claims 1
Classifications
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- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/0036—Flash degasification
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/10—Vacuum distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D7/00—Sublimation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0004—Crystallisation cooling by heat exchange
- B01D9/0013—Crystallisation cooling by heat exchange by indirect heat exchange
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/004—Fractional crystallisation; Fractionating or rectifying columns
- B01D9/0045—Washing of crystals, e.g. in wash columns
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/02—Crystallisation from solutions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/02—Crystallisation from solutions
- B01D9/04—Crystallisation from solutions concentrating solutions by removing frozen solvent therefrom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
-
- 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
-
- 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
- C08G63/785—Preparation processes characterised by the apparatus used
-
- 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
- C08G63/88—Post-polymerisation treatment
- C08G63/90—Purification; Drying
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F124/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
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- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W90/00—Enabling technologies or technologies with a potential or indirect contribution to greenhouse gas [GHG] emissions mitigation
- Y02W90/10—Bio-packaging, e.g. packing containers made from renewable resources or bio-plastics
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (14)
1. Postupak proizvodnje polilaktične kiseline, naznačen time, da obuhvaća sljedeće korake:
(i) izvođenje polimerizacije otvora prstena koristeći katalizator, te ili spoj koji uništava katalizator ili aditiv za krajnji pokrovni sloj (endcapping aditiv), u svrhu dobivanja sirove polilaktične kiseline s MW većim od 10.000 g/mol,
(ii) pročišćavanje sirove polilaktične kiseline putem odstranjivanja i odvajanja spojeva s niskim ključanjem, koji sadrže laktid i nečistoće iz sirove polilaktične kiseline, pomoću otplinjavanja spojeva s niskim ključanjem kao toka plinovite faze,
pri čemu otplinjavanje djeluje pod djelomičnim tlakom laktida, manjim od 20 mbara, poželjno manje od 10 mbara, posebno poželjno manje od 5 mbara,
(iii) pročišćavanje laktida iz procesa otplinjavanja i odstranjivanje nečistoća iz toka plinovite faze od evaporiranih spojeva niskog ključanja, pomoću kristalizacije putem desublimacije iz plinovite faze,
pri čemu se laktid pročišćava i odstranjene nečistoće uključuju ostatak katalizatora kao i spoj koji sadrži barem jednu hidroksil-skupinu, tako da se pročišćeni laktid polimerizira njegovim vraćanjem i unošenjem u proces polimerizacije otvora prstena.
2. Postupak prema zahtjevu 1, naznačen time, da se desublimacija odvija na ohlađenoj površini.
3. Postupak prema zahtjevu 1 ili 2, naznačen time, da uređaj za kristalizaciju i uređaj za otplinjavanje rade pod uglavnom istim uvjetima u vakuumu, što je rezultat izravne povezanosti uređaja za kristalizaciju i uređaja za otplinjavanje.
4. Postupak prema bilo kojem zahtjevu od 1 do 3, naznačen time, da se desublimacija i kristalizacija odvijaju u istom uređaju.
5. Postupak prema bilo kojem zahtjevu od 3 do 4, naznačen time, da uređaj za kristalizaciju nema tok inertnog plina.
6. Postupak prema bilo kojem zahtjevu od 1 do 5, naznačen time, da evaporirani tok plinovite faze iz procesa otplinjavanja, sadrži najmanje 30% laktida, poželjno najmanje 60%, a najbolje najmanje 90%.
7. Postupak prema bilo kojem zahtjevu od 1 do 6, naznačen time, da se laktid prvo podvrgava koraku orošavanja, nakon čega slijedi korak otapanja, prije nego što se on unese natrag u proces polimerizacije otvora prstena.
8. Postupak prema bilo kojem zahtjevu od 1 do 7, naznačen time, da uklonjene nečistoće uključuju ili organometalni spoj ili karboksilnu kiselinu.
9. Postupak prema bilo kojem zahtjevu od 1 do 8, naznačen time, da se barem dio od pročišćenog toka iz kristalizacije u proizvodnji pročišćenog laktida, reciklira u koraku purifikacije sirovog laktida, u koraku pred-polimerizacije i dimerizacije, ili u koraku odstranjivanja otopine.
10. Postupak prema bilo kojem zahtjevu od 7 do 9, naznačen time, da se tekućina iz koraka orošavanja, sakuplja i rekristalizira, kako bi se obnovio laktid.
11. Uređaj za izvršenje postupka prema zahtjevu 1, naznačen time, da on sadrži sljedeće:
polimerizacijski reaktor za izvođenje polimerizacije otvora prstena, u svrhu dobivanja sirove polilaktične kiseline,
naprava za otplinjavanje koja služi za odvajanje spojeva niskog ključanja iz sirove polilaktične kiseline, koji sadrže laktid i nečistoće, i
naprava za kristalizaciju koja služi za pročišćavanje laktida i za odstranjivanje nečistoća, pomoću desublimacije i kristalizacije u toj istoj napravi za kristalizaciju.
12. Uređaj prema zahtjevu 11, naznačen time, da između naprave za kristalizaciju i naprave za otplinjavanje, nisu raspoređena prigušna sredstva ni vakuumske pumpe.
13. Uređaj prema bilo kojem zahtjevu od 11 do 12, naznačen time, da je između naprave za otplinjavanje i naprave za kristalizaciju, smješten izmjenjivač topline.
14. Uređaj prema bilo kojem zahtjevu od 11 do 13, naznačen time, da naprava za kristalizaciju ima površine s izmjenjivanjem topline, koje služe za stvrdnjavanje plinovitog toka.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11154930 | 2011-02-18 | ||
| EP11154929 | 2011-02-18 | ||
| EP11187571 | 2011-11-02 | ||
| EP11187572 | 2011-11-02 | ||
| PCT/EP2011/070168 WO2012110117A1 (en) | 2011-02-18 | 2011-11-15 | Method for the manufacture of a polyhydroxy-carboxylic acid |
| EP11784642.8A EP2675539B1 (en) | 2011-02-18 | 2011-11-15 | Method for the manufacture of a polyhydroxy-carboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20150985T1 true HRP20150985T1 (hr) | 2015-11-06 |
Family
ID=44993555
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150985TT HRP20150985T1 (hr) | 2011-02-18 | 2015-09-17 | Postupak proizvodnje polihidroksi-karboksilne kiseline |
| HRP20150986TT HRP20150986T1 (hr) | 2011-02-18 | 2015-09-17 | Postupak proizvodnje polihidroksi-karboksilne kiseline |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150986TT HRP20150986T1 (hr) | 2011-02-18 | 2015-09-17 | Postupak proizvodnje polihidroksi-karboksilne kiseline |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US9637587B2 (hr) |
| EP (2) | EP2675539B1 (hr) |
| JP (2) | JP2014511150A (hr) |
| KR (2) | KR101801176B1 (hr) |
| CN (2) | CN103502235B (hr) |
| AU (2) | AU2011359119A1 (hr) |
| BR (2) | BR112013019911B1 (hr) |
| CA (2) | CA2827593C (hr) |
| ES (2) | ES2547147T3 (hr) |
| HR (2) | HRP20150985T1 (hr) |
| HU (2) | HUE025611T2 (hr) |
| MX (2) | MX343860B (hr) |
| PL (2) | PL2675799T3 (hr) |
| RU (1) | RU2572548C2 (hr) |
| WO (2) | WO2012110118A1 (hr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2649369T3 (es) * | 2012-12-18 | 2018-01-11 | Uhde Inventa-Fischer Gmbh | Dispositivo y procedimiento para la separación de un diéster cíclico de masas fundidas poliméricas |
| EP2928574B1 (en) * | 2013-01-14 | 2021-09-29 | Sulzer Management AG | Multi-stage crystallisation process and apparatus to purify a compound |
| EP2777791A1 (en) * | 2013-03-11 | 2014-09-17 | Sulzer Chemtech AG | Process and apparatus for purification of a stream containing a cyclic ester of an alpha-hydroxycarboxylic acid |
| WO2016009793A1 (ja) * | 2014-07-14 | 2016-01-21 | 宇部興産株式会社 | 高純度ビニレンカーボネート、非水電解液、及びそれを用いた蓄電デバイス |
| EP2998337A1 (en) | 2014-09-17 | 2016-03-23 | Sulzer Chemtech AG | A method for stabilizing a condensed phase composition including a cyclic ester for example in a process of manufacturing a polyester |
| RU2713408C2 (ru) * | 2014-09-17 | 2020-02-05 | Зульцер Хемтех Аг | Способ стабилизации композиции конденсированной фазы, содержащей циклический сложный эфир, в процессе производства сложного полиэфира из лактида |
| EP3056490A1 (en) * | 2015-02-13 | 2016-08-17 | PURAC Biochem BV | Method for manufacturing lactide |
| EP3108947A1 (en) * | 2015-06-24 | 2016-12-28 | Sulzer Chemtech AG | Semi-continuous crystallization method and apparatus |
| RU2621342C1 (ru) * | 2016-07-29 | 2017-06-02 | Федеральное государственное автономное образовательное учреждение высшего образования "Национальный исследовательский Томский государственный университет" (ТГУ, НИ ТГУ) | Приемник вакуумного камерного реактора синтеза гликолида и лактида |
| WO2019217328A1 (en) | 2018-05-07 | 2019-11-14 | California Institute Of Technology | Gel and polymer based flow meters |
| US11668613B2 (en) * | 2019-05-06 | 2023-06-06 | California Institute Of Technology | ABA type block co-polymers for temperature sensing and flow meters |
| EP3838849A1 (en) * | 2019-12-19 | 2021-06-23 | Sulzer Management AG | A process for controlling of the purification of waste fluid generated during a petrochemical process using an incinerator |
| KR20210119909A (ko) | 2020-03-25 | 2021-10-06 | 삼성전자주식회사 | 열 또는 적외광 감지용 복합체 및 이를 포함하는 소자 |
| CN112920583B (zh) * | 2021-04-14 | 2022-05-06 | 中国科学院长春应用化学研究所 | 一种具有快速结晶能力的聚l-乳酸发泡材料及其制备方法 |
| BE1029670B1 (fr) * | 2021-08-02 | 2023-03-06 | Futerro Sa | Procédé de récupération de lactide et d'acide lactique lors des étapes de production de polylactide (PLA) |
| CN114405049A (zh) * | 2021-12-09 | 2022-04-29 | 西安航天华威化工生物工程有限公司 | 一种高浓度乳酸结晶提纯的系统及方法 |
| CN114672010A (zh) * | 2022-04-01 | 2022-06-28 | 温州邦鹿化工有限公司 | 一种聚乳酸连续聚合脱挥方法及装置 |
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| FR2799386B1 (fr) | 1999-10-12 | 2001-12-28 | Befs Prokem | Procede de purification de produits organiques par cristallisation fractionnee a vitesse de circulation variable |
| FR2821360B1 (fr) * | 2001-02-27 | 2003-05-30 | Sod Conseils Rech Applic | Procede de preparation de polyesters avec des fonctions acides libres intracatenaires |
| NL1017751C2 (nl) | 2001-03-30 | 2002-10-22 | Korporam B V | Werkwijze en meetsysteem voor het bepalen van het kristalgehalte van een kristalsuspensie-mengsel. |
| NL1017956C2 (nl) | 2001-04-27 | 2002-11-05 | Korporam B V | Meertraps-tegenstroom kristallisatie-inrichting. |
| BE1015060A3 (fr) | 2002-08-06 | 2004-09-07 | Brussels Biotech Nv Sa | Procede de production de polylactide au depart d'une solution d'acide lactique ou d'un de ses derives. |
| ATE300345T1 (de) | 2002-09-10 | 2005-08-15 | Niro Process Technology Bv | Methode und apparat zur gewinnung einer reinen substanz aus einer unreinen lösung durch kristallisation |
| RU2301230C2 (ru) * | 2005-03-23 | 2007-06-20 | Российский химико-технологический университет им. Д.И. Менделеева | Способ получения лактида |
| RU2008116595A (ru) | 2005-09-28 | 2009-11-10 | Тейт Энд Лайл Паблик Лимитед Компани (Gb) | Новый способ получения полимолочной кислоты |
| EP1937746A1 (en) | 2005-09-28 | 2008-07-02 | Tate & Lyle PLC | Novel process for the preparation of polylactic acid |
| WO2007148975A2 (en) * | 2007-03-14 | 2007-12-27 | Niro Process Technology B.V. | Purification of lactide rich streams |
| ES2383493T3 (es) | 2008-03-31 | 2012-06-21 | Purac Biochem Bv | Método para la fabricación de polilactida estable |
| RU2404198C2 (ru) | 2008-11-12 | 2010-11-20 | Федеральное государственное унитарное предприятие "Ордена Трудового Красного Знамени Научно-исследовательский физико-химический институт имени Л.Я. Карпова" | Способ получения сополимеров стирола с молочной кислотой |
-
2011
- 2011-11-15 HU HUE11785651A patent/HUE025611T2/en unknown
- 2011-11-15 US US13/985,770 patent/US9637587B2/en active Active
- 2011-11-15 BR BR112013019911-3A patent/BR112013019911B1/pt active IP Right Grant
- 2011-11-15 CA CA2827593A patent/CA2827593C/en active Active
- 2011-11-15 KR KR1020137021585A patent/KR101801176B1/ko active IP Right Grant
- 2011-11-15 KR KR1020137021584A patent/KR101806256B1/ko active IP Right Grant
- 2011-11-15 WO PCT/EP2011/070169 patent/WO2012110118A1/en active Application Filing
- 2011-11-15 RU RU2013142454/04A patent/RU2572548C2/ru active
- 2011-11-15 HU HUE11784642A patent/HUE026448T2/en unknown
- 2011-11-15 CN CN201180067630.5A patent/CN103502235B/zh active Active
- 2011-11-15 EP EP11784642.8A patent/EP2675539B1/en active Active
- 2011-11-15 MX MX2013009482A patent/MX343860B/es active IP Right Grant
- 2011-11-15 AU AU2011359119A patent/AU2011359119A1/en not_active Abandoned
- 2011-11-15 ES ES11785651.8T patent/ES2547147T3/es active Active
- 2011-11-15 JP JP2013553811A patent/JP2014511150A/ja active Pending
- 2011-11-15 WO PCT/EP2011/070168 patent/WO2012110117A1/en active Application Filing
- 2011-11-15 PL PL11785651T patent/PL2675799T3/pl unknown
- 2011-11-15 PL PL11784642T patent/PL2675539T3/pl unknown
- 2011-11-15 US US13/985,778 patent/US20130331543A1/en not_active Abandoned
- 2011-11-15 CA CA2827595A patent/CA2827595C/en active Active
- 2011-11-15 JP JP2013553810A patent/JP2014511149A/ja active Pending
- 2011-11-15 CN CN201180067634.3A patent/CN103442776B/zh active Active
- 2011-11-15 MX MX2013009481A patent/MX343859B/es active IP Right Grant
- 2011-11-15 AU AU2011359120A patent/AU2011359120A1/en not_active Abandoned
- 2011-11-15 EP EP11785651.8A patent/EP2675799B1/en active Active
- 2011-11-15 BR BR112013018066-8A patent/BR112013018066B1/pt active IP Right Grant
- 2011-11-15 ES ES11784642.8T patent/ES2547146T3/es active Active
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2015
- 2015-02-26 US US14/632,469 patent/US20150166721A1/en not_active Abandoned
- 2015-09-17 HR HRP20150985TT patent/HRP20150985T1/hr unknown
- 2015-09-17 HR HRP20150986TT patent/HRP20150986T1/hr unknown
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