KR20130040190A - 전처리된 에폭시화 촉매를 사용하는 프로필렌 옥사이드의 제조방법 - Google Patents
전처리된 에폭시화 촉매를 사용하는 프로필렌 옥사이드의 제조방법 Download PDFInfo
- Publication number
- KR20130040190A KR20130040190A KR1020127027601A KR20127027601A KR20130040190A KR 20130040190 A KR20130040190 A KR 20130040190A KR 1020127027601 A KR1020127027601 A KR 1020127027601A KR 20127027601 A KR20127027601 A KR 20127027601A KR 20130040190 A KR20130040190 A KR 20130040190A
- Authority
- KR
- South Korea
- Prior art keywords
- catalyst
- pretreated
- methanol
- propylene
- activated
- 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.)
- Ceased
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 106
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims description 60
- 238000006735 epoxidation reaction Methods 0.000 title claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 249
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 35
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 34
- 239000007800 oxidant agent Substances 0.000 claims abstract description 11
- 230000001590 oxidative effect Effects 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 150000003608 titanium Chemical class 0.000 claims abstract description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 26
- 239000010936 titanium Substances 0.000 claims description 21
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 18
- 229910052719 titanium Inorganic materials 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 9
- -1 peroxide compound Chemical class 0.000 claims description 7
- 229910021536 Zeolite Inorganic materials 0.000 claims description 5
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 5
- 239000010457 zeolite Substances 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000007605 air drying Methods 0.000 claims 1
- 230000009257 reactivity Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 20
- 230000000694 effects Effects 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 230000008901 benefit Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 238000002411 thermogravimetry Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/80—Mixtures of different zeolites
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epoxy Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31739010P | 2010-03-25 | 2010-03-25 | |
| US61/317,390 | 2010-03-25 | ||
| PCT/US2011/000523 WO2011119217A1 (en) | 2010-03-25 | 2011-03-22 | Process for producing propylene oxide using a pretreated epoxidation catalyst |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20130040190A true KR20130040190A (ko) | 2013-04-23 |
Family
ID=44065153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127027601A Ceased KR20130040190A (ko) | 2010-03-25 | 2011-03-22 | 전처리된 에폭시화 촉매를 사용하는 프로필렌 옥사이드의 제조방법 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8703983B2 (enExample) |
| EP (1) | EP2550259A1 (enExample) |
| JP (1) | JP2013523633A (enExample) |
| KR (1) | KR20130040190A (enExample) |
| CN (1) | CN102822158A (enExample) |
| BR (1) | BR112012024298A8 (enExample) |
| TW (1) | TWI523689B (enExample) |
| WO (1) | WO2011119217A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5223980B2 (ja) | 2011-04-21 | 2013-06-26 | 大日本印刷株式会社 | 色材分散液、カラーフィルター用着色樹脂組成物、カラーフィルター、液晶表示装置及び有機発光表示装置 |
| CN106795126B (zh) * | 2014-07-29 | 2018-10-26 | 赢创德固赛有限公司 | 烯烃的环氧化方法 |
| KR101878627B1 (ko) | 2015-04-09 | 2018-07-13 | 라이온델 케미칼 테크놀로지, 엘.피. | 메틸벤질 알코올의 산화로부터 프로필렌 옥사이드를 형성하는 방법 |
| CN113149934A (zh) * | 2015-11-26 | 2021-07-23 | 赢创运营有限公司 | 生产环氧丙烷的设备 |
| CN108191794B (zh) * | 2017-12-29 | 2020-02-11 | 中触媒新材料股份有限公司 | 一种丙烯环氧化反应方法 |
| CN108689966A (zh) * | 2018-05-21 | 2018-10-23 | 华东师范大学 | 一种环氧丙烷的制备方法 |
| CN111085264B (zh) * | 2018-10-23 | 2022-12-06 | 华东理工大学 | 基于碳多孔陶瓷的整构式改性ts-1催化剂及制备方法与应用 |
| CN112742472B (zh) * | 2021-01-19 | 2022-03-15 | 中国科学院大连化学物理研究所 | 一种高活性低副产的环氧化催化剂的制备方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1127311B (it) | 1979-12-21 | 1986-05-21 | Anic Spa | Materiale sintetico,cristallino,poroso costituito da ossidi di silicio e titanio,metodo per la sua preparazione e suoi usi |
| IT1152299B (it) * | 1982-07-28 | 1986-12-31 | Anic Spa | Procedimento per l'espossidazione di composti olefinici |
| EP0230949B1 (en) * | 1986-01-28 | 1992-07-22 | ENIRICERCHE S.p.A. | A process for the epoxydation of olefinic compounds |
| JPH1025285A (ja) * | 1996-07-08 | 1998-01-27 | Mitsubishi Gas Chem Co Inc | オレフィン化合物のエポキシ化法 |
| JP4016461B2 (ja) * | 1997-09-04 | 2007-12-05 | ダイソー株式会社 | オレフィンの選択的エポキシ化法 |
| PT987259E (pt) * | 1998-03-26 | 2002-11-29 | Repsol Quimica Sa | Processo de epoxidacao de compostos olefinicos com peroxido de hidrogenio |
| DE19835907A1 (de) | 1998-08-07 | 2000-02-17 | Basf Ag | Verfahren zur Umsetzung einer organischen Verbindung mit einem Hydroperoxid |
| DE10032885A1 (de) | 2000-07-06 | 2002-01-17 | Basf Ag | Verfahren zur Herstellung von Propylenoxid |
| CN1159218C (zh) * | 2001-05-30 | 2004-07-28 | 中国石油化工股份有限公司 | Mfi晶体结构铬硅分子筛的合成方法 |
| DE10135296A1 (de) | 2001-07-19 | 2003-01-30 | Basf Ag | Verfahren zur Herstellung von Propylenoxid |
| WO2003027087A1 (en) | 2001-09-21 | 2003-04-03 | Sumitomo Chemical Company, Limited | Process for preparation of propylene oxide |
| US6417378B1 (en) * | 2001-10-09 | 2002-07-09 | Arco Chemical Technology, L.P. | Direct epoxidation process using pre-treated titanium zeolite |
| DE10233382A1 (de) | 2002-07-23 | 2004-01-29 | Basf Ag | Verfahren zur kontinuierlich betriebenen Reindestillation des bei der koppel-produktfreien Synthese von Propylenoxid anfallenden 1.2-Propylenglykols |
| DE10240129B4 (de) | 2002-08-30 | 2004-11-11 | Basf Ag | Integriertes Verfahren zur Synthese von Propylenoxid |
| US6960671B2 (en) | 2002-09-20 | 2005-11-01 | Arco Chemical Technology, L.P. | Process for direct oxidation of propylene to propylene oxide and large particle size titanium silicalite catalysts for use therein |
| EP1424331A1 (en) * | 2002-11-26 | 2004-06-02 | Degussa AG | Process for the epoxidation of olefins |
| DE10317519A1 (de) | 2003-04-16 | 2004-11-04 | Basf Ag | Verfahren zur Herstellung von Propylenoxid |
| US6884898B1 (en) | 2003-12-08 | 2005-04-26 | Arco Chemical Technology, L.P. | Propylene oxide process |
| US6867312B1 (en) | 2004-03-17 | 2005-03-15 | Arco Chemical Technology, L.P. | Propylene oxide process |
| US20050277542A1 (en) * | 2004-06-14 | 2005-12-15 | Kaminsky Mark P | Catalyst regeneration process |
| US7057056B1 (en) * | 2004-12-17 | 2006-06-06 | Lyondell Chemical Technology, L.P. | Epoxidation catalyst |
| KR101166932B1 (ko) * | 2005-07-27 | 2012-07-19 | 에스케이이노베이션 주식회사 | 티타늄 함유 분자체 촉매의 재생방법 |
| TW201201910A (en) * | 2010-03-25 | 2012-01-16 | Dow Global Technologies Llc | A pretreated epoxidation catalyst and a process for producing an olefin therewith |
-
2011
- 2011-03-16 TW TW100108896A patent/TWI523689B/zh not_active IP Right Cessation
- 2011-03-22 CN CN2011800160999A patent/CN102822158A/zh active Pending
- 2011-03-22 BR BR112012024298A patent/BR112012024298A8/pt not_active IP Right Cessation
- 2011-03-22 KR KR1020127027601A patent/KR20130040190A/ko not_active Ceased
- 2011-03-22 US US13/637,072 patent/US8703983B2/en not_active Expired - Fee Related
- 2011-03-22 EP EP11713535A patent/EP2550259A1/en not_active Withdrawn
- 2011-03-22 JP JP2013501249A patent/JP2013523633A/ja active Pending
- 2011-03-22 WO PCT/US2011/000523 patent/WO2011119217A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP2550259A1 (en) | 2013-01-30 |
| US8703983B2 (en) | 2014-04-22 |
| JP2013523633A (ja) | 2013-06-17 |
| TWI523689B (zh) | 2016-03-01 |
| US20130018196A1 (en) | 2013-01-17 |
| TW201138968A (en) | 2011-11-16 |
| WO2011119217A1 (en) | 2011-09-29 |
| BR112012024298A8 (pt) | 2017-03-21 |
| CN102822158A (zh) | 2012-12-12 |
| BR112012024298A2 (pt) | 2015-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8703983B2 (en) | Process for producing propylene oxide using a pretreated epoxidation catalyst | |
| US8697895B2 (en) | Process for producing an oxirane | |
| EP2462130B1 (en) | Process for producing propylene oxide | |
| TWI485143B (zh) | 烯烴的環氧化 | |
| US8981132B2 (en) | Pretreated epoxidation catalyst and a process for producing an olefin therewith | |
| EP2670741B1 (en) | Process for separating phases of a mixture containing an oxirane | |
| CN102666517B (zh) | 环氧化丙烯 |
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Comment text: Notification of reason for refusal Patent event date: 20170612 Patent event code: PE09021S01D |
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