HRP20150986T1 - Postupak proizvodnje polihidroksi-karboksilne kiseline - Google Patents
Postupak proizvodnje polihidroksi-karboksilne kiseline Download PDFInfo
- Publication number
- HRP20150986T1 HRP20150986T1 HRP20150986TT HRP20150986T HRP20150986T1 HR P20150986 T1 HRP20150986 T1 HR P20150986T1 HR P20150986T T HRP20150986T T HR P20150986TT HR P20150986 T HRP20150986 T HR P20150986T HR P20150986 T1 HRP20150986 T1 HR P20150986T1
- Authority
- HR
- Croatia
- Prior art keywords
- crystallization
- lactide
- flow
- polylactic acid
- degassing
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 12
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 238000002425 crystallisation Methods 0.000 claims 18
- 230000008025 crystallization Effects 0.000 claims 18
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 6
- 238000007872 degassing Methods 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
- 239000003054 catalyst Substances 0.000 claims 3
- 239000007792 gaseous phase Substances 0.000 claims 3
- 238000006116 polymerization reaction Methods 0.000 claims 3
- 238000000746 purification Methods 0.000 claims 3
- 239000000725 suspension Substances 0.000 claims 3
- 239000000654 additive Substances 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 239000012071 phase Substances 0.000 claims 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000006471 dimerization reaction Methods 0.000 claims 1
- 239000011552 falling film Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- 238000007142 ring opening reaction Methods 0.000 claims 1
- 230000003068 static effect Effects 0.000 claims 1
- 238000005406 washing 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
-
- 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
Claims (13)
1. Postupak proizvodnje polilaktične kiseline, naznačen time, da obuhvaća sljedeće korake:
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,
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,
pročišćavanje laktida iz procesa otplinjavanja i odstranjivanje nečistoća iz toka plinovite faze od evaporiranih spojeva niskog ključanja, pomoću kondenzacije evaporiranog toka plinovite faze, u svrhu dobivanja kondenziranog toka, te uzastopno otopljene kristalizacije kondenziranog toka,
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 otopljena kristalizacija izvodi pomoću slojevite ili suspenzijske kristalizacije.
3. Postupak prema zahtjevu 1 ili 2, naznačen time, da evaporirani tok plinovite faze iz procesa otplinjavanja, sadrži najmanje 30% laktida, poželjno najmanje 60%, a najbolje najmanje 90%.
4. Postupak prema bilo kojem zahtjevu od 1 do 3, naznačen time, da se kristal koji se dobiva kao rezultat otopljene kristalizacije od kondenziranog toka, kristalizira u sljedećem stupnju kristalizacije.
5. Postupak prema bilo kojem zahtjevu od 2 do 4, naznačen time, da slojevita kristalizacija obuhvaća korak orošavanja, nakon kojega slijedi korak otapanja stvrdnute frakcije prisutne u kristalnom obliku na površini za kristalizaciju.
6. Postupak prema bilo kojem zahtjevu od 1 do 5, naznačen time, da uklonjene nečistoće uključuju ili organometalni spoj ili karboksilnu kiselinu.
7. Postupak prema bilo kojem zahtjevu od 1 do 6, naznačen time, da se za otopljenu kristalizaciju upotrebljava uređaj koji nema tok inertnog plina.
8. Postupak prema bilo kojem zahtjevu od 1 do 7, 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.
9. Postupak prema bilo kojem zahtjevu od 1 do 8, naznačen time, da se matična tekućina iz kristalizacije i/ili tekućina iz koraka orošavanja, sakupljaju i rekristaliziraju, kako bi se obnovio laktid.
10. 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 iz kondenziranog toka,
pri čemu je između naprave za otplinjavanje i naprave za kristalizaciju, raspoređen kondenzator za kondenzaciju toka plinovite faze u svrhu dobivanja kondenziranog toka.
11. Uređaj prema zahtjevu 10, naznačen time, da naprava za kristalizaciju je naprava za slojevitu kristalizaciju ili naprava za suspenzijsku kristalizaciju.
12. Uređaj prema zahtjevu 11, naznačen time, da naprava za slojevitu kristalizaciju je statična naprava ili naprava za kristalizaciju s padajućom folijom.
13. Uređaj prema zahtjevu 11, naznačen time, da naprava za suspenzijsku kristalizaciju sadrži šuplji valjak za pranje.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11154929 | 2011-02-18 | ||
| EP11154930 | 2011-02-18 | ||
| EP11187572 | 2011-11-02 | ||
| EP11187571 | 2011-11-02 | ||
| PCT/EP2011/070169 WO2012110118A1 (en) | 2011-02-18 | 2011-11-15 | Method for the manufacture of a polyhydroxy-carboxylic acid |
| EP11785651.8A EP2675799B1 (en) | 2011-02-18 | 2011-11-15 | Method for the manufacture of a polyhydroxy-carboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20150986T1 true HRP20150986T1 (hr) | 2015-11-06 |
Family
ID=44993555
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150986TT HRP20150986T1 (hr) | 2011-02-18 | 2015-09-17 | Postupak proizvodnje polihidroksi-karboksilne kiseline |
| HRP20150985TT HRP20150985T1 (hr) | 2011-02-18 | 2015-09-17 | Postupak proizvodnje polihidroksi-karboksilne kiseline |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150985TT HRP20150985T1 (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) | AU2011359120A1 (hr) |
| BR (2) | BR112013018066B1 (hr) |
| CA (2) | CA2827595C (hr) |
| ES (2) | ES2547147T3 (hr) |
| HR (2) | HRP20150986T1 (hr) |
| HU (2) | HUE026448T2 (hr) |
| MX (2) | MX343860B (hr) |
| PL (2) | PL2675539T3 (hr) |
| RU (1) | RU2572548C2 (hr) |
| WO (2) | WO2012110117A1 (hr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2746313B1 (de) * | 2012-12-18 | 2017-08-30 | Uhde Inventa-Fischer GmbH | Vorrichtung und Verfahren zur Abtrennung eines cyclischen Diesters aus Polymerschmelzen |
| WO2014108285A1 (en) * | 2013-01-14 | 2014-07-17 | Sulzer Chemtech 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 |
| JP6620745B2 (ja) * | 2014-07-14 | 2019-12-18 | 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 |
| US10059799B2 (en) | 2014-09-17 | 2018-08-28 | Sulzer Chemtech Ag | Method for stabilizing a condensed phase composition including a cyclic ester in a process of manufacturing a polyester or of lactide |
| 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 |
| 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 |
| US11255870B2 (en) | 2018-05-07 | 2022-02-22 | 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 |
| US11912807B2 (en) | 2020-03-25 | 2024-02-27 | Samsung Electronics Co., Ltd. | Composite for sensing heat or infrared light and device including same |
| 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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| 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 |
| AU2005336726A1 (en) | 2005-09-28 | 2007-04-05 | Tate & Lyle Public Limited Company | Novel process for the preparation of polylactic acid |
| RU2008116595A (ru) | 2005-09-28 | 2009-11-10 | Тейт Энд Лайл Паблик Лимитед Компани (Gb) | Новый способ получения полимолочной кислоты |
| WO2007148975A2 (en) * | 2007-03-14 | 2007-12-27 | Niro Process Technology B.V. | Purification of lactide rich streams |
| WO2009121830A1 (en) | 2008-03-31 | 2009-10-08 | Purac Biochem Bv | Method for manufacturing stable polylactide |
| 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 WO PCT/EP2011/070168 patent/WO2012110117A1/en active Application Filing
- 2011-11-15 ES ES11785651.8T patent/ES2547147T3/es active Active
- 2011-11-15 MX MX2013009482A patent/MX343860B/es active IP Right Grant
- 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 CA CA2827595A patent/CA2827595C/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 AU AU2011359120A patent/AU2011359120A1/en not_active Abandoned
- 2011-11-15 HU HUE11785651A patent/HUE025611T2/en unknown
- 2011-11-15 PL PL11784642T patent/PL2675539T3/pl unknown
- 2011-11-15 CN CN201180067634.3A patent/CN103442776B/zh active Active
- 2011-11-15 US US13/985,770 patent/US9637587B2/en active Active
- 2011-11-15 BR BR112013018066-8A patent/BR112013018066B1/pt active IP Right Grant
- 2011-11-15 WO PCT/EP2011/070169 patent/WO2012110118A1/en active Application Filing
- 2011-11-15 MX MX2013009481A patent/MX343859B/es active IP Right Grant
- 2011-11-15 AU AU2011359119A patent/AU2011359119A1/en not_active Abandoned
- 2011-11-15 JP JP2013553811A patent/JP2014511150A/ja active Pending
- 2011-11-15 RU RU2013142454/04A patent/RU2572548C2/ru active
- 2011-11-15 EP EP11785651.8A patent/EP2675799B1/en active Active
- 2011-11-15 JP JP2013553810A patent/JP2014511149A/ja active Pending
- 2011-11-15 PL PL11785651T patent/PL2675799T3/pl unknown
- 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 US US13/985,778 patent/US20130331543A1/en not_active Abandoned
- 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 HRP20150986TT patent/HRP20150986T1/hr unknown
- 2015-09-17 HR HRP20150985TT patent/HRP20150985T1/hr unknown
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