KR960010070A - 3급 n-알케닐 카르복실산 아미드류의 제조용 촉매 및 이 촉매를 이용한 3급 n-알케닐 카르복실산 아미드류의 제조방법 - Google Patents
3급 n-알케닐 카르복실산 아미드류의 제조용 촉매 및 이 촉매를 이용한 3급 n-알케닐 카르복실산 아미드류의 제조방법 Download PDFInfo
- Publication number
- KR960010070A KR960010070A KR1019950030488A KR19950030488A KR960010070A KR 960010070 A KR960010070 A KR 960010070A KR 1019950030488 A KR1019950030488 A KR 1019950030488A KR 19950030488 A KR19950030488 A KR 19950030488A KR 960010070 A KR960010070 A KR 960010070A
- Authority
- KR
- South Korea
- Prior art keywords
- tertiary
- carboxylic acid
- alkenyl
- acid amide
- hydroxyalkyl
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract 8
- 238000004519 manufacturing process Methods 0.000 title claims abstract 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract 3
- 238000006297 dehydration reaction Methods 0.000 claims abstract 3
- 229910052710 silicon Inorganic materials 0.000 claims abstract 3
- 239000010703 silicon Substances 0.000 claims abstract 3
- BAMUPQJDKBGDPU-UHFFFAOYSA-N n-(2-hydroxyethyl)formamide Chemical group OCCNC=O BAMUPQJDKBGDPU-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 230000018044 dehydration Effects 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract 2
- -1 alkenyl carboxylic acid Chemical class 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
- B01J23/04—Alkali metals
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/182—Phosphorus; Compounds thereof with silicon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
본 발명은 알칼리 금속 및 알칼리 토금속으로 구성된 군으로부터 선택된 1종 이상의 원소 및 규소를 함유하는 산화물로서, 3급 N-(2-히드록시에틸) 카르복실산 아미드를 기상 분자간 탈수 반응시켜 3급 N-알케닐 카르복실산 아미드를 합성하는데 사용되는 촉매를 제공한다. 이 촉매는 임의의 보조 원료의 사용없이 3급 N-(2-히드록시알킬) 카르복실산 아미드로부터 3급 N-알케닐 카르복실산 아미드의 지속적이고 효과적인 제조를 가능하게 하여, 보조 원료로부터 파생된 임의의 부산물(폐기물)의 발생없이 3급 N-알케닐 카르복실산 아미드를 간단하고 안전하게 제조하는 것을 가능하게 하여준다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 알칼리 금속 및 알칼리 토금속으로 구성된 군으로부터 선택된 1종 이상의 원소 및 규소를 함유하는 산화물로서, 3급 N-(2-히드록시에틸) 카르복실산 아미드를 기상 분자간 탈수 반응시켜 3급 N-알케닐 카르복실산 아미드를 합성하는데 사용되는 촉매
- 제1항에 있어서, 하기의 일반식(1)로 나타낸 산화물인 촉매:MaSibXcOd(1)(식중, M은 알칼리 금속 및 알칼리 토금속으로 구성된 군으로부터 선택된 1종 이상의 원소이고; Si는 규소이고; X는 붕소, 알루미늄 및 인으로 구성된 군으로부터 선택된 1종 이상의 원소이고; O는 산소이고; a,b,c 및 d는 각각 상응하는 원소의 원자수이고, 단, a=1, b=1-500 및 c=0-1 이고 d는 a,b 및 c의 값에 의해 결정되는 수이고, 각 구성 원소는 상호 결합되어 있다)
- 제1 또는 2항에 있어서, 3급 N-(2-히드록시알킬) 카르복실산 아미드는 하기의 일반식(2)로 나타낸 N-(2-히드록시에틸)-N'-알킬-아미드 화합물이고, 3급 N-알케닐 카르복실산 아미드는 하기의 일반식(3)으로 나타낸 N-비닐-N'-알킬-아미드 화합물인 촉매:@ (2)@ (3)(식중, R1및 R2는 독립적으로 탄소수 1-6의 탄화수소기이다).
- 제1 또는 2항에 있어서, 3급 N-(2-히드록시알킬) 카르복실산 아미드는 N-(2-히드록시에틸)-2-피릴리돈이고, 3급 N-알케닐 카르복실산 아미드는 N-비닐-2-피롤리돈인 촉매
- 제1 또는 2항에 있어서, 3급 N-(2-히드록시알킬) 카르복실산 아미드가 하기의 일반식(4)로 나타낸 N-(2-히드록시알킬)-N'-알킬-아미드 화합물이고, 3급 N-알케닐 카르복실산 아미드가 하기의 일반식(5) 및 (6)으로 나타낸 N-알케닐-N'-알킬-아미드 화합물인 촉매@ (4)@ (5)@ (6)(식중, R1, R2및 R3는 독립적인 기로서, R1및 R2는 각각 탄소수 1-6의 탄화수소기이고, R3은 수소원자이거나 탄소수 1-6의 탄화수소기이다).
- 제1항 또는 2항의 촉매를 사용함을 특징으로 하는, 3급 N-(2-히드록시알킬)카르복실산 아미드의 기상 분자간 탈수 반응에 의한 3급 N-알케닐 카르복실산 아미드의 제조방법
- 제6항에 있어서, 3급 N-(2-히드록시알킬) 카르복실산 아미드는 하기의 일반식(2)로 나타낸 N-(2-히드록시에틸)-N'-알킬-아미드 화합물이고, 3급 N-알케닐 카르복실산 아미드는 하기의 일반식(3)으로 나타낸 N-비닐-N'-알킬-아미드 화합물인 제조방법:@ (2)@ (3)(식중, R1및 R2는 독립적으로 탄소수 1-6의 탄화수소기이다).
- 제6항에 있어서, 3급 N-(2-히드록시알킬) 카르복실산 아미드는 N-(2-히드록시에틸)-2-피릴리돈이고, 3급 N-알케닐 카르복실산 아미드는 N-비닐-2-피롤리돈인 제조방법
- 제6항에 있어서, 3급 N-(2-히드록시알킬) 카르복실산 아미드가 하기의 일반식(4)로 나타낸 N-(2-히드록시알킬)-N'-알킬-아미드 화합물이고, 3급 N-알케닐 카르복실산 아미드가 하기의 일반식(5) 및 (6)으로 나타낸 N-알케닐-N'-알킬-아미드 화합물인 제조방법;@ (4)@ (5)@ (6)(식중, R1, R2및 R3는 독립적인 기로서, R1및 R2는 각각 탄소수 1-6의 탄화수소기이고, R3은 수소원자이거나 탄소수 1-6의 탄화수소기이다).※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP94-222895 | 1994-09-19 | ||
JP22289594 | 1994-09-19 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR960010070A true KR960010070A (ko) | 1996-04-20 |
KR100388696B1 KR100388696B1 (ko) | 2003-11-14 |
Family
ID=16789554
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019950030488A KR100388696B1 (ko) | 1994-09-19 | 1995-09-18 | 3급n-알케닐카르복실산아미드류의제조용촉매및이촉매를이용한3급n-알케닐카르복실산아미드류의제조방법 |
Country Status (4)
Country | Link |
---|---|
US (1) | US5625076A (ko) |
EP (1) | EP0701998B1 (ko) |
KR (1) | KR100388696B1 (ko) |
DE (1) | DE69503728T2 (ko) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5849830A (en) * | 1995-06-07 | 1998-12-15 | Amcol International Corporation | Intercalates and exfoliates formed with N-alkenyl amides and/or acrylate-functional pyrrolidone and allylic monomers, oligomers and copolymers and composite materials containing same |
DE19521588A1 (de) * | 1995-06-14 | 1996-12-19 | Bayer Ag | N-substituierte cis-N-Propenyl-acetamide und Verfahren zu ihrer Herstellung |
JPH09241220A (ja) * | 1996-03-05 | 1997-09-16 | Nippon Shokubai Co Ltd | 3級アミン化合物の製造法 |
JP2939433B2 (ja) * | 1996-03-18 | 1999-08-25 | 株式会社日本触媒 | 環式n−ビニルカルボン酸アミドの製造方法 |
DE19801549A1 (de) * | 1998-01-16 | 1999-07-22 | Basf Ag | Verfahren zur Herstellung von N-Alkenylcarbonsäureamiden |
JP3435598B2 (ja) | 1999-10-22 | 2003-08-11 | 株式会社日本触媒 | N−ビニル−2−ピロリドンの回収方法 |
KR100533484B1 (ko) * | 2000-01-28 | 2005-12-05 | 가부시키가이샤 닛폰 쇼쿠바이 | 기체상 탈수 반응 방법 |
JP3315105B2 (ja) | 2000-02-10 | 2002-08-19 | 株式会社日本触媒 | ビニルピロリドン系重合体の製造法 |
JP3999022B2 (ja) | 2002-04-04 | 2007-10-31 | 株式会社日本触媒 | ビニルピロリドン系重合体 |
JP2004345994A (ja) * | 2003-05-21 | 2004-12-09 | Nippon Shokubai Co Ltd | N−ビニル−2−ピロリドンの精製方法 |
US6982337B1 (en) * | 2004-07-28 | 2006-01-03 | Lyondell Chemical Technology, L.P. | Process for making N-vinyl-2-pyrrolidone |
SG189244A1 (en) | 2010-10-07 | 2013-05-31 | Rohm & Haas | Process for production of methacrylic acid ester |
US9199910B2 (en) | 2012-06-04 | 2015-12-01 | Rohm And Haas Company | Process for production of methacrylic acid esters |
BR112015031389B1 (pt) | 2013-06-26 | 2021-01-26 | Rohm And Haas Company | processo para produzir ésteres de ácido metacrílico |
CN106622309B (zh) * | 2016-09-27 | 2019-06-11 | 西安元创化工科技股份有限公司 | 一种n-羟乙基吡咯烷酮脱水催化剂及其制备方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2669570A (en) * | 1951-08-24 | 1954-02-16 | Celanese Corp | Production of n-vinyl pyrrolidone |
US2775599A (en) * | 1952-04-10 | 1956-12-25 | Schenley Ind Inc | Process for the production of n-vinylpyrrolidone-2 |
DE2135211A1 (de) * | 1970-07-17 | 1972-01-20 | Mitsubishi Petrochemical Co , Ltd , Tokio | Verfahren zur Herstellung von N Vinylpyrrolidon |
JPS5421330B2 (ko) * | 1971-10-14 | 1979-07-30 | ||
US4567300A (en) * | 1984-01-14 | 1986-01-28 | Mitsubishi Chemical Industries Limited | Process for producing N-substituted formamides |
AU591208B2 (en) * | 1985-12-23 | 1989-11-30 | Nippon Shokubai Kagaku Kogyo Co. Ltd. | Catalyst for vapor-phase intramolecular dehydration reaction of alkanolamines |
AU590653B2 (en) * | 1985-12-27 | 1989-11-09 | Nippon Shokubai Kagaku Kogyo Co. Ltd. | Catalyst for vapor-phase intermolecular dehydration reaction of alkanolamines |
US4774218A (en) * | 1985-12-27 | 1988-09-27 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Catalyst for vapor-phase intramolecular dehydration reaction of alkanolamines |
WO1991019696A1 (en) * | 1990-06-21 | 1991-12-26 | Nippon Shokubai Co., Ltd. | Process for producing n-substituted aziridine compound |
DE4302325A1 (de) * | 1993-01-28 | 1994-08-04 | Basf Ag | Verfahren zur Herstellung von N-Alkenylpyrrolidonen |
US5527963A (en) * | 1994-10-16 | 1996-06-18 | Mitsubishi Chemical Corporation | Production of N-vinylformamide |
-
1995
- 1995-09-18 US US08/529,324 patent/US5625076A/en not_active Expired - Lifetime
- 1995-09-18 KR KR1019950030488A patent/KR100388696B1/ko not_active IP Right Cessation
- 1995-09-19 EP EP95306597A patent/EP0701998B1/en not_active Expired - Lifetime
- 1995-09-19 DE DE69503728T patent/DE69503728T2/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DE69503728D1 (de) | 1998-09-03 |
EP0701998A1 (en) | 1996-03-20 |
KR100388696B1 (ko) | 2003-11-14 |
US5625076A (en) | 1997-04-29 |
DE69503728T2 (de) | 1999-01-14 |
EP0701998B1 (en) | 1998-07-29 |
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