AU2011376834A1 - Preparation of methacrylic acid - Google Patents
Preparation of methacrylic acid Download PDFInfo
- Publication number
- AU2011376834A1 AU2011376834A1 AU2011376834A AU2011376834A AU2011376834A1 AU 2011376834 A1 AU2011376834 A1 AU 2011376834A1 AU 2011376834 A AU2011376834 A AU 2011376834A AU 2011376834 A AU2011376834 A AU 2011376834A AU 2011376834 A1 AU2011376834 A1 AU 2011376834A1
- Authority
- AU
- Australia
- Prior art keywords
- methacrylic acid
- precipitation
- aqueous solution
- process according
- area
- 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 238000001556 precipitation Methods 0.000 claims abstract description 132
- 238000000034 method Methods 0.000 claims abstract description 95
- 125000005395 methacrylic acid group Chemical group 0.000 claims abstract description 58
- 239000012535 impurity Substances 0.000 claims abstract description 46
- 239000007864 aqueous solution Substances 0.000 claims abstract description 44
- 238000000926 separation method Methods 0.000 claims abstract description 44
- 239000007787 solid Substances 0.000 claims abstract description 27
- 239000012452 mother liquor Substances 0.000 claims abstract description 22
- 230000003647 oxidation Effects 0.000 claims description 27
- 238000007254 oxidation reaction Methods 0.000 claims description 27
- 238000001816 cooling Methods 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 238000013019 agitation Methods 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 12
- 238000010791 quenching Methods 0.000 claims description 11
- 230000000171 quenching effect Effects 0.000 claims description 10
- 239000007789 gas Substances 0.000 description 30
- 239000012071 phase Substances 0.000 description 30
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 28
- 239000002244 precipitate Substances 0.000 description 23
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 20
- 238000000605 extraction Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 15
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- -1 N-substituted methacryl amides Chemical class 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 2
- 229940018557 citraconic acid Drugs 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 238000007561 laser diffraction method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 238000003921 particle size analysis Methods 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2011/079765 WO2013037132A1 (en) | 2011-09-16 | 2011-09-16 | Preparation of methacrylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2011376834A1 true AU2011376834A1 (en) | 2014-02-13 |
Family
ID=47882551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2011376834A Abandoned AU2011376834A1 (en) | 2011-09-16 | 2011-09-16 | Preparation of methacrylic acid |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20140187817A1 (enExample) |
| EP (1) | EP2755941A1 (enExample) |
| JP (1) | JP6153527B2 (enExample) |
| KR (1) | KR101877099B1 (enExample) |
| CN (2) | CN103796983A (enExample) |
| AU (1) | AU2011376834A1 (enExample) |
| BR (1) | BR112014006346A2 (enExample) |
| IN (1) | IN2014CN02726A (enExample) |
| MX (1) | MX2014002527A (enExample) |
| RU (1) | RU2014114865A (enExample) |
| SA (1) | SA112330848B1 (enExample) |
| SG (1) | SG2014012652A (enExample) |
| TW (1) | TW201323400A (enExample) |
| WO (1) | WO2013037132A1 (enExample) |
| ZA (1) | ZA201401599B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3023408A1 (de) * | 2014-11-19 | 2016-05-25 | Evonik Röhm GmbH | Optimiertes Verfahren zur Herstellung von Methacrylsäure |
| EP3603805B1 (en) * | 2017-03-27 | 2024-01-03 | Mitsubishi Chemical Corporation | Catalyst and catalyst group |
| WO2018181226A1 (ja) | 2017-03-27 | 2018-10-04 | 三菱ケミカル株式会社 | 触媒及び触媒群 |
| EP3889127A1 (en) | 2020-04-03 | 2021-10-06 | Röhm GmbH | Improved safe method for tandem c-4 oxidation to methacrylic acid |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0780810B2 (ja) * | 1987-08-05 | 1995-08-30 | 三井東圧化学株式会社 | メタクリル酸水溶液の処理方法 |
| JPH0780809B2 (ja) * | 1987-08-05 | 1995-08-30 | 三井東圧化学株式会社 | メタクリル酸水溶液の処理方法 |
| CA1316545C (en) * | 1987-06-27 | 1993-04-20 | Morimasa Kuragano | Quenching process of reaction product gas containing methacrylic acid and treatment method of quenched liquid |
| JPH0780811B2 (ja) * | 1987-08-05 | 1995-08-30 | 三井東圧化学株式会社 | メタクリル酸水溶液の処理方法 |
| JPH0764775B2 (ja) * | 1988-03-08 | 1995-07-12 | 三井東圧化学株式会社 | メタクロレインの吸収方法 |
| JPH05262691A (ja) * | 1992-03-19 | 1993-10-12 | Nippon Shokubai Co Ltd | フマル酸の製造方法 |
| JP3417085B2 (ja) * | 1994-09-16 | 2003-06-16 | 栗田工業株式会社 | 殺菌剤包接化合物の製造方法 |
| JP3279491B2 (ja) * | 1996-12-16 | 2002-04-30 | 株式会社日本触媒 | （メタ）アクリル酸の製造方法 |
| JP2002128728A (ja) * | 2000-10-19 | 2002-05-09 | Mitsubishi Rayon Co Ltd | メタクリル酸の精製方法 |
| DE10211686A1 (de) * | 2002-03-15 | 2003-10-02 | Stockhausen Chem Fab Gmbh | (Meth)Acrylsäurekristall und Verfahren zur Herstellung und Aufreinigung von wässriger (Meth)Acrylsäure |
| DE102004034316B4 (de) * | 2004-07-15 | 2015-07-16 | Evonik Degussa Gmbh | Ein Verfahren zur Herstellung von (Meth)Acrylsäure |
| EP2085376B1 (en) * | 2008-01-30 | 2012-09-05 | Evonik Röhm GmbH | Process for preparation of high purity methacrylic acid |
-
2011
- 2011-09-16 KR KR1020147006576A patent/KR101877099B1/ko active Active
- 2011-09-16 CN CN201180073469.2A patent/CN103796983A/zh active Pending
- 2011-09-16 BR BR112014006346A patent/BR112014006346A2/pt not_active IP Right Cessation
- 2011-09-16 JP JP2014530067A patent/JP6153527B2/ja active Active
- 2011-09-16 WO PCT/CN2011/079765 patent/WO2013037132A1/en not_active Ceased
- 2011-09-16 US US14/240,547 patent/US20140187817A1/en not_active Abandoned
- 2011-09-16 EP EP11872304.8A patent/EP2755941A1/en not_active Withdrawn
- 2011-09-16 SG SG2014012652A patent/SG2014012652A/en unknown
- 2011-09-16 RU RU2014114865/04A patent/RU2014114865A/ru not_active Application Discontinuation
- 2011-09-16 CN CN201710587973.3A patent/CN107382705B/zh active Active
- 2011-09-16 IN IN2726CHN2014 patent/IN2014CN02726A/en unknown
- 2011-09-16 AU AU2011376834A patent/AU2011376834A1/en not_active Abandoned
- 2011-09-16 MX MX2014002527A patent/MX2014002527A/es unknown
-
2012
- 2012-09-12 TW TW101133299A patent/TW201323400A/zh unknown
- 2012-09-15 SA SA112330848A patent/SA112330848B1/ar unknown
-
2014
- 2014-03-03 ZA ZA2014/01599A patent/ZA201401599B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN2014CN02726A (enExample) | 2015-07-03 |
| KR20140060526A (ko) | 2014-05-20 |
| SA112330848B1 (ar) | 2015-10-12 |
| RU2014114865A (ru) | 2015-10-27 |
| SG2014012652A (en) | 2014-08-28 |
| CN107382705B (zh) | 2021-08-10 |
| JP2014532039A (ja) | 2014-12-04 |
| BR112014006346A2 (pt) | 2017-04-04 |
| CN107382705A (zh) | 2017-11-24 |
| TW201323400A (zh) | 2013-06-16 |
| WO2013037132A1 (en) | 2013-03-21 |
| ZA201401599B (en) | 2015-08-26 |
| KR101877099B1 (ko) | 2018-08-09 |
| CN103796983A (zh) | 2014-05-14 |
| JP6153527B2 (ja) | 2017-06-28 |
| MX2014002527A (es) | 2014-05-28 |
| EP2755941A1 (en) | 2014-07-23 |
| US20140187817A1 (en) | 2014-07-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |