JP5033349B2 - N−アルケニルカルボン酸3級アミド組成物 - Google Patents
N−アルケニルカルボン酸3級アミド組成物 Download PDFInfo
- Publication number
- JP5033349B2 JP5033349B2 JP2006124309A JP2006124309A JP5033349B2 JP 5033349 B2 JP5033349 B2 JP 5033349B2 JP 2006124309 A JP2006124309 A JP 2006124309A JP 2006124309 A JP2006124309 A JP 2006124309A JP 5033349 B2 JP5033349 B2 JP 5033349B2
- Authority
- JP
- Japan
- Prior art keywords
- composition
- acid tertiary
- tertiary amide
- alkenylcarboxylic acid
- amine compound
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 43
- 239000002253 acid Substances 0.000 title claims description 25
- 150000003511 tertiary amides Chemical class 0.000 title claims description 25
- 238000003860 storage Methods 0.000 claims description 29
- -1 amine compound Chemical class 0.000 claims description 28
- 150000001412 amines Chemical class 0.000 claims description 16
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical group NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 11
- 150000004982 aromatic amines Chemical class 0.000 claims description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000001139 pH measurement Methods 0.000 claims description 2
- 230000000052 comparative effect Effects 0.000 description 6
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- CMBRHCVQODXRRS-UHFFFAOYSA-N 4-n-butan-2-ylbenzene-1,4-diamine Chemical compound CCC(C)NC1=CC=C(N)C=C1 CMBRHCVQODXRRS-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002443 hydroxylamines Chemical class 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- FQYRLEXKXQRZDH-UHFFFAOYSA-N quinolin-4-ylamine Natural products C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229960004050 aminobenzoic acid Drugs 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Detergent Compositions (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Description
メチルアミン(MA)、エチルアミン(EA)、イソプロピルアミン、t−ブチルアミン(tBA)、ジメチルアミン、ジエチルアミン、トリエチルアミン、シクロヘキシルアミンなどの脂肪族アミン類;モノエタノールアミン(MEA)、ジエタノールアミン、トリエタノールアミンなどのアルカノールアミン類;N,N−ジメチルヒドロキシルアミンなどのヒドロキシルアミン類;アンモニア;アニリン、トルイジン、ベンジルアミン、2−ナフチルアミン、p−アミノ安息香酸などの芳香族アミン類;4−アミノキノリンなどの複素環式芳香族アミン類。
100mLスクリュー管に組成物サンプル100gを入れて蓋をし、空気雰囲気下30℃の温度に設定したオーブン(三洋電機社製)に保管する。
50mLのスクリュー管にpH6から7に調整した純水45gを秤量し、次いで該サンプル5gを秤量して混合し、該組成物の10質量%水溶液を作製する。1分以内にpH計にセットし、25℃で1分間、200rpmで攪拌後、2分間静置して、その時のpH値を読み取る。
<色価(APHA)の測定方法>
色度試験用試薬(色度1000:和光純薬製)を純水で希釈し、各種の色度標準液を調製する。25mL比色管に組成物サンプル25mLを入れ、標準液と比較して同色度のAPHA番号を測定値とする。
NVPに各種のアミン類を添加し、貯蔵の開始時と3ヶ月経過後とにおいて、pHと色価(APHA)について測定し、下記表1に示す。
NVPを、表2に示される内容で、200kg入りケミドラム(ポリエチレン内袋)に投入した。
NVPを、表2に示される内容で、18L入りハイブリッド缶に投入した。その後、窒素ガスを充填し、容器を密閉した。
Claims (11)
- N−アルケニルカルボン酸3級アミドと、フェニレンジアミン骨格を有しないアミン化合物(A)を含有し、
前記フェニレンジアミン骨格を有しないアミン化合物(A)は、メチルアミン、エチルアミン、イソプロピルアミン、t−ブチルアミン、ジメチルアミン、ジエチルアミン、シクロヘキシルアミンから選択される脂肪族アミン類、およびアルカノールアミン類よりなる群から選ばれた少なくとも1種であり、
前記N−アルケニルカルボン酸3級アミドの含有率は、全組成物中80質量%以上であることを特徴とするN−アルケニルカルボン酸3級アミド組成物。 - 前記アミン化合物(A)は、20℃における蒸気圧が3×10−6hPa以上のアミンである請求項1記載の組成物。
- 前記フェニレンジアミン骨格を有しないアミン化合物(A)の含有量は、前記N−アルケニルカルボン酸3級アミドの質量に対し、1ppm以上、3質量%以下の範囲にある請求項1または2に記載の組成物。
- さらに芳香族アミン(B)を含有する請求項1〜3のいずれか1項に記載の組成物。
- さらに溶媒を加えてなる請求項1〜4のいずれか1項に記載の組成物。
- 前記溶媒の添加量は、得られる組成物の総量に対し、20質量%までである請求項5に記載の組成物。
- 前記組成物を、空気雰囲気下30℃の温度で3ヶ月間、促進試験を行った後の所定のpH測定法によるpHが、8〜12の範囲にある請求項1〜6のいずれか1項に記載の組成物。
- 前記組成物を、空気雰囲気下30℃の温度で3ヶ月間、促進試験を行った後の色価(APHA)変動値が、貯蔵開始前の値に比べて50以内である請求項1〜7のいずれか1項に記載の組成物。
- 前記N−アルケニルカルボン酸3級アミドは、N−ビニル−ピロリドンである請求項1〜8のいずれか1項に記載の組成物。
- 前記N−アルケニルカルボン酸3級アミドの含有率は、全組成物中90質量%以上である、請求項1〜9のいずれか1項に記載の組成物。
- 請求項1〜10のいずれか1項に記載の組成物を調製する段階を含む、N−アルケニルカルボン酸3級アミドの貯蔵方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006124309A JP5033349B2 (ja) | 2005-04-28 | 2006-04-27 | N−アルケニルカルボン酸3級アミド組成物 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005130641 | 2005-04-28 | ||
JP2005130641 | 2005-04-28 | ||
JP2006124309A JP5033349B2 (ja) | 2005-04-28 | 2006-04-27 | N−アルケニルカルボン酸3級アミド組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006328061A JP2006328061A (ja) | 2006-12-07 |
JP5033349B2 true JP5033349B2 (ja) | 2012-09-26 |
Family
ID=37949713
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006124309A Active JP5033349B2 (ja) | 2005-04-28 | 2006-04-27 | N−アルケニルカルボン酸3級アミド組成物 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20090306402A1 (ja) |
EP (1) | EP1874728B1 (ja) |
JP (1) | JP5033349B2 (ja) |
CN (1) | CN101166717A (ja) |
WO (1) | WO2006118330A1 (ja) |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3048555A (en) * | 1959-01-14 | 1962-08-07 | Dow Chemical Co | Method for stabilizing aqueous solutions of water-soluble n-vinyl heterocyclic polymers and copolymers by adding water-soluble amines |
US3959358A (en) * | 1975-01-08 | 1976-05-25 | Nalco Chemical Company | Polymerization inhibition of acrylate esters |
US4732695A (en) * | 1987-02-02 | 1988-03-22 | Texo Corporation | Paint stripper compositions having reduced toxicity |
US5340488A (en) * | 1989-11-15 | 1994-08-23 | Petro Chemical Products, Inc. | Composition for cleaning an internal combustion engine |
EP0467851A1 (en) * | 1990-07-20 | 1992-01-22 | Ciba-Geigy Ag | Stabilized monomer compositions |
US5258138A (en) * | 1990-07-20 | 1993-11-02 | Ciba-Geigy Corporation | Process for stabilizing ethylenically unsaturated compounds and stabilized monomer compositions |
PT627911E (pt) * | 1992-02-28 | 2001-04-30 | Univ Texas | Hidrogeis biodegradaveis fotopolimerizaveis como materiais de contacto de tecidos e veiculos de libertacao controlada |
DE4405199A1 (de) * | 1994-02-18 | 1995-08-24 | Basf Ag | Verfahren zum Binden von in Roh-N-Vinyl-pyrrolidon-(2) enthaltenen chemischen Verunreinigungen |
US6911216B1 (en) * | 1994-10-12 | 2005-06-28 | Genzyme Corporation | Targeted delivery via biodegradable polymers |
DE19638868A1 (de) * | 1996-09-23 | 1998-03-26 | Basf Ag | Stabilisierte Monomerenzusammensetzung |
FR2777884B1 (fr) * | 1998-04-28 | 2000-07-13 | Rhodia Chimie Sa | Composition et procede d'inhibition de la polymerisation radicalaire de monomeres aromatiques a insaturation ethylenique |
FR2787444B1 (fr) * | 1998-12-22 | 2001-02-09 | Rhodia Chimie Sa | Composition et procede d'inhibition de la polymerisation radicalaire de monomeres aliphatiques a insaturation ethylenique |
DE19906316A1 (de) * | 1999-02-16 | 2000-08-17 | Basf Ag | Stabilisierte Zusammensetzungen von O- und N-Vinylverbindungen und Verwendung von Ammoniumsalzen als Stabilisierungsmittel |
US6417356B1 (en) * | 2001-01-18 | 2002-07-09 | Isp Investments Inc. | Stabilization of vinylether and vinyl lactam formulations against hydrolysis |
US6525147B1 (en) * | 2001-06-20 | 2003-02-25 | Baker Hughes Incorporated | Use of diamines and alkanolamines to inhibit unsaturated monomer polymerization |
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 |
US20050079228A1 (en) * | 2003-05-30 | 2005-04-14 | Ashish Jaiswal | Clear, stable topical compositions of clarithromycin and processes for their preparation |
DE10346135A1 (de) * | 2003-10-01 | 2004-10-07 | Basf Ag | Radikalfänger als Stabilisatoren polymerisationsfähiger Verbindungen |
EP1518916A1 (de) * | 2003-09-26 | 2005-03-30 | Basf Aktiengesellschaft | Radikalfänger als stabilisatoren polymerisationsfähiger Verbindungen |
JP5121470B2 (ja) * | 2007-01-26 | 2013-01-16 | 株式会社日本触媒 | ポリビニルピロリドン粉体組成物 |
-
2006
- 2006-04-27 CN CNA2006800142684A patent/CN101166717A/zh active Pending
- 2006-04-27 WO PCT/JP2006/309214 patent/WO2006118330A1/en active Application Filing
- 2006-04-27 EP EP06746046.9A patent/EP1874728B1/en active Active
- 2006-04-27 JP JP2006124309A patent/JP5033349B2/ja active Active
- 2006-04-27 US US11/919,340 patent/US20090306402A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
EP1874728A1 (en) | 2008-01-09 |
JP2006328061A (ja) | 2006-12-07 |
EP1874728B1 (en) | 2014-03-19 |
CN101166717A (zh) | 2008-04-23 |
WO2006118330A1 (en) | 2006-11-09 |
US20090306402A1 (en) | 2009-12-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA1116513A (en) | Composition containing 1,2-benzisothiazolin-3-one | |
JP3623792B2 (ja) | 安定な液状配合物およびそれらの使用 | |
US5196138A (en) | Preparation of mixed lithium amide reagents | |
EP3275910B1 (en) | Condensation product of 1-amino-2-propanol and formaldehyde and the use thereof for reducing the amount of hydrogen sulphide in liquids and gases | |
SG194958A1 (en) | Synergistic combination for inhiibiting polymerization of vinyl monomers | |
JP5033349B2 (ja) | N−アルケニルカルボン酸3級アミド組成物 | |
TWI259186B (en) | Immediate termination of free radical polymerizations | |
Houk et al. | Syn and anti transition states in the addition of ammonia to cyanoacetylene. Formation of a stable Zwitterionic intermediate | |
De Sousa et al. | Effect of cyclohexylene bridges on the metal ion size based selectivity of ligands in aqueous solution | |
ES2197687T3 (es) | Flegmatizacion mejorada de peroxidos de cetona ciclicos. | |
JPH06507940A (ja) | 希ガスを用いる貯蔵の間の化学物質の酸化の制御方法 | |
JP3914029B2 (ja) | 安定化されたビニルピロリドン系重合体組成物 | |
JPH11140010A (ja) | オルトフタルアルデヒド安定化組成物 | |
WO2012098811A1 (ja) | スルフォラン類組成物 | |
CN113166052B (zh) | 一种n-乙烯基吡咯烷酮单体的阻聚剂及其应用 | |
GB2024243A (en) | Stabilization of 1,1,1- trichloroethane | |
GB973920A (en) | Sulphenic acid derivatives | |
JP2599197B2 (ja) | N―フェニルマレイミド系化合物のアクリロニトリル溶液の安定化剤 | |
JP4612195B2 (ja) | O−及びn−ビニル化合物の安定化された組成物及び安定剤としてのアンモニウム塩の使用 | |
JPH11255765A (ja) | スルフォランの安定化方法 | |
JPWO2008026680A1 (ja) | カルボジイミド誘導体の安定化方法及びその安定化組成物 | |
US5574197A (en) | Method of making a stable non-pyrophoric lithium diorganoamide solution | |
US10662151B1 (en) | Process for preparing DTEA HCl | |
JP4649984B2 (ja) | キシリレンジアミン組成物、およびキシリレンジアミンの保存方法 | |
WO2016167361A1 (ja) | Pdを実質的に含まない有機化合物の製造方法及び水素ガスを用いた有機化合物からPdを除去する新規な方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20090220 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120321 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120518 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120605 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120702 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5033349 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150706 Year of fee payment: 3 |