JP4380990B2 - ピリドン染料、それらの製造方法ならびに着色プラスチックまたはカラーポリマー粒子の製造におけるそれらの使用 - Google Patents
ピリドン染料、それらの製造方法ならびに着色プラスチックまたはカラーポリマー粒子の製造におけるそれらの使用 Download PDFInfo
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- JP4380990B2 JP4380990B2 JP2002571768A JP2002571768A JP4380990B2 JP 4380990 B2 JP4380990 B2 JP 4380990B2 JP 2002571768 A JP2002571768 A JP 2002571768A JP 2002571768 A JP2002571768 A JP 2002571768A JP 4380990 B2 JP4380990 B2 JP 4380990B2
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- pyridone azo
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- Expired - Lifetime
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- 0 Cc1c(*)c(*)c(*)cc1* Chemical compound Cc1c(*)c(*)c(*)cc1* 0.000 description 4
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
- C09B62/24—Azo dyes
- C09B62/245—Monoazo dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/12—Disazo dyes in which the coupling component is a heterocyclic compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Pyridine Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Description
Aは、ベンゼン、ナフタレン、ジフェニル、アゾベンゼン、チオフェン、ベンゾチアゾール、ベンゾイソチアゾール、チアジアゾール、インダゾール、ベンゾトリアゾール、ピラゾール、アントラキノン、ナフタル酸イミド、クロモン、フタルイミドまたはジフェニレンオキシド系列のジアゾ成分の基であり、
R1は、水素、非置換またはヒドロキシ−もしくはフェニル−置換C1〜C6アルキル(それはアルキル鎖について、C3より上で、1個以上の酸素原子により中断されていてもよい)であるか、あるいはR2の意味を有し、
R2は、式(2)、(3)、(4)、(5)、(6)または(7):
R1とR2は−NR1R2中の窒素原子と一緒になって、ヘテロ環を形成し、
Yはシアノ、−CONH2または−CH2SO3Hであり、そして
nは2〜6の整数である)
で示される基である〕
で示されるピリドンアゾ染料に関する。
Aとして特に好ましいものは、式(8):
R8は水素、ハロゲン、シアノ、−CF3、−COOR11〔ここで、R11は、アルキル基が酸素で中断されていてもよいC1〜C4アルキルである〕、あるいはベンジルまたは−SO2R12(ここで、R12は−NR13R14またはフェニルであり、そしてR13は水素またはC1〜C4アルキルであり、R14はC1〜C4アルキルまたはベンジルである)である、
R9は、水素またはハロゲンであり、そして
R10は、水素または基−SO2−O−C6H5である}
で示される基である。
Yは好ましくはシアノである。
R7、R8およびR9としてのハロゲンは、臭素、ヨウ素および特に塩素である。
で示されるカップリング成分にカップリングする。
(A) 水140.0mlを反応容器に入れ、0〜5℃に冷却した。次いで、30分かけて、エチレンジアミン405.2ml、その後シアノ酢酸エチル215.4mlを滴下し、温度は冷却により20℃より低く保ち続けた。その後、反応混合物を20℃で16時間攪拌し、過剰のエチレンジアミンを60℃で減圧留去し、そして混合物を40℃で1時間攪拌した。
次いで、アセト酢酸エチル253.0mlを滴下し、滴下終了までに温度を70℃に上げた。アセト酢酸エチルの滴下が完了したときすぐに、30%アンモニア水168.0ml、その後プロパノール1400.0mlを加え、そして反応混合物を70〜75℃で16時間攪拌した。得られた懸濁液をろ過し、エタノール1500.0mlに入れ、20℃で14時間攪拌し、そして再度ろ過した。ろ過ケーキを合計1000.0mlのエタノールで数回洗浄し、そして乾燥した。
式(55):
式(58):
その後、水300.0mlを加え、そして完全に反応させた反応マスを70℃に加熱し、吸引ろ過し、水洗し、そして乾燥した。
式(12):
(A) ジエチレントリアミン111.95mlを反応フラスコに入れ、そしてシアノ酢酸エチル236.95mlを20℃で加え、温度は約75℃に上昇した。反応混合物を30分間攪拌し、次いで、94%エタノール1000.0mlを加え、そして混合物を72℃(還流)で2時間攪拌した。その後、アセト酢酸エチル278.3ml、30%アンモニア水溶液168.0mlおよび94%エタノール3000.0mlを順次加え、混合物を還流下、さらに41時間攪拌した。
得られた懸濁液を75℃で吸引ろ過し、次いで合計500.0mlの94%エタノールで数回洗浄し、その後、94%エタノール2000.0mlを加え、そして混合物を20℃で14時間攪拌した。次いで、懸濁液を吸引ろ過し、ろ過ケーキを合計1000.0mlの94%エタノールで数回洗浄し、減圧下で乾燥した。
式(57):
式(59):
反応混合物を0〜5℃で4時間攪拌し、次いでpH4.6に調整し、そして20℃でさらに17時間攪拌した。得られた懸濁液を吸引ろ過し、80%DMF25.0ml、エタノールおよび水で順次、pHが6より大きくなるまで洗浄し、そして乾燥した。
式(10):
実施例1および2に記載した方法と同様にして、表1〜16に列挙された下記の染料を製造することも可能であり、それらは同じくポリエステルを黄色の色調に染めた。
ポリエステル粒子(PET Arnite D04−300、DSM)1200.00gを130℃で4時間予備乾燥させ、次いで式(14)のピリドンアゾ染料0.24gと、「ローラーラック(roller rack)」混合装置中で15分間、一分あたり60回転で均一に混合した。均一な混合物を、6つの加熱ゾーンを有する押出し機(Collin, D-85560 Ebersbergからのツインスクリュー25mm)で、最高温度275℃で押出し、水で冷却し、造粒機(MAPAG AG, CH-3001 BernからのTurb Etuve TE 25)で造粒し、その後、130℃で4時間乾燥させた。
得られた黄色のポリエステル粒は良好な全般的堅牢性、特に、非常に良好な光堅牢性および高温光堅牢性を有していた。
ポリエステル粒子(PET Arnite D04−300、DSM)1200.00gを75℃で4時間予備乾燥させ、次いで式(14)のピリドンアゾ染料0.60gおよび式(63):
得られた黄色のポリエステル粒は良好な全般的堅牢性、特に、非常に良好な光堅牢性および高温光堅牢性を有していた。
Claims (6)
- 式(1)または(10):
Aは、式(8):
R8はハロゲン、シアノ、−CF3、−COOR11〔ここで、R11は、アルキル基が酸素で中断されていてもよいC1〜C4アルキルである〕あるいはベンジルまたは−SO2R12(ここで、R12は−NR13R14またはフェニルであり、そしてR13は水素またはC1〜C4アルキルであり、R14はC1〜C4アルキルまたはベンジルである)である、
R9は、水素またはハロゲンであり、そして
R10は、水素または基−SO2−O−C6H5である}
の基であり、
R1は、水素、非置換またはヒドロキシ−もしくはフェニル−置換C1〜C6アルキル(それは、アルキル鎖について、C3より上で、1個以上の酸素原子により中断されていてもよい)であるか、あるいはR2の意味を有し、
R2は、式(3)または(4):
R1とR2は、−NR1R2中の窒素原子と一緒になって、ヘテロ環を形成し、Yはシアノ、−CONH2または−CH2SO3Hであり、そしてnは2〜6の整数である)で示される基である〕
で示されるピリドンアゾ染料。 - 請求項1記載の1種以上の式(1)のピリドンアゾ染料を着色プラスティックまたはカラーポリマー粒子の材料に混和することを含む、着色プラスチックまたはカラーポリマー粒子の製造方法。
- 請求項1記載の式(1)のピリドンアゾ染料およびUV吸収剤の組み合わせを用いることを含む、着色プラスチックまたはカラーポリマー粒子の製造方法。
- 着色プラスチックまたはカラーポリマー粒子の製造における、請求項1記載のピリドンアゾ染料の使用。
- 請求項3または請求項4のいずれかに記載の、プラスチックまたはカラーポリマー粒子。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH4402001 | 2001-03-09 | ||
CH8222001 | 2001-05-07 | ||
CH13862001 | 2001-07-25 | ||
PCT/EP2002/002150 WO2002072707A1 (en) | 2001-03-09 | 2002-02-28 | Pyridone dyes, a process for their preparation and their use in the production of coloured plastics or polymeric colour particles |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2004526836A JP2004526836A (ja) | 2004-09-02 |
JP2004526836A5 JP2004526836A5 (ja) | 2009-02-19 |
JP4380990B2 true JP4380990B2 (ja) | 2009-12-09 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2002571768A Expired - Lifetime JP4380990B2 (ja) | 2001-03-09 | 2002-02-28 | ピリドン染料、それらの製造方法ならびに着色プラスチックまたはカラーポリマー粒子の製造におけるそれらの使用 |
Country Status (11)
Country | Link |
---|---|
US (1) | US6953846B2 (ja) |
EP (1) | EP1368431B1 (ja) |
JP (1) | JP4380990B2 (ja) |
KR (1) | KR20030090664A (ja) |
CN (1) | CN1288211C (ja) |
AT (1) | ATE380221T1 (ja) |
BR (1) | BR0207944A (ja) |
CA (1) | CA2434837A1 (ja) |
DE (1) | DE60223907T2 (ja) |
MX (1) | MXPA03006339A (ja) |
WO (1) | WO2002072707A1 (ja) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MXPA05002144A (es) * | 2002-08-30 | 2005-05-23 | Ciba Sc Holding Ag | Metodo para producir plastico de color o particulas de color polimericas. |
ES2268408T3 (es) * | 2002-10-18 | 2007-03-16 | Clariant Finance (Bvi) Limited | Compuestos azoicos. |
JP4879752B2 (ja) * | 2003-12-23 | 2012-02-22 | チバ ホールディング インコーポレーテッド | 有機素材を光から保護する方法 |
JP4512507B2 (ja) * | 2004-07-09 | 2010-07-28 | 富士フイルム株式会社 | ピリドンアゾ化合物およびこの互変異性体を含み着色剤含有硬化性組成物、カラーフィルタおよびその製造方法 |
US20070207331A1 (en) * | 2006-03-06 | 2007-09-06 | Pearson Jason C | Azo compounds and coating compositions containing the azo compounds |
TWI483997B (zh) * | 2008-05-14 | 2015-05-11 | Sumitomo Chemical Co | 偶氮化合物或其鹽類 |
TWI461408B (zh) * | 2008-07-02 | 2014-11-21 | Clariant Finance Bvi Ltd | 酸染料 |
TW201134886A (en) * | 2009-12-25 | 2011-10-16 | Sumitomo Chemical Co | Pyridone compound |
TW201129638A (en) * | 2009-12-25 | 2011-09-01 | Sumitomo Chemical Co | Pyridone compound |
DE112014004448T5 (de) * | 2013-09-27 | 2016-06-23 | Canon Kabushiki Kaisha | Farbstoffverbindung, Tinte und Resistzusammensetzung für einen Farbfilter |
US9658553B2 (en) | 2013-09-27 | 2017-05-23 | Canon Kabushiki Kaisha | Toner |
EP2868705A1 (en) * | 2013-10-29 | 2015-05-06 | DyStar Colours Distribution GmbH | Metal free acid dyes, process for their production and their use |
CN104231660A (zh) * | 2014-08-01 | 2014-12-24 | 浙江昱泰染化科技有限公司 | 一种单偶氮化合物、制品与应用 |
CN112679979B (zh) * | 2020-12-29 | 2023-09-01 | 浙江永合新材料科技有限公司 | 一种苯并三唑类紫外线吸收剂中间体偶氮染料的制备方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH552661A (de) | 1968-11-12 | 1974-08-15 | Ciba Geigy Ag | Verfahren zur herstellung neuer azofarbstoffe. |
CA972353A (en) | 1970-12-22 | 1975-08-05 | Ciba-Geigy Ag | Azo compounds, their manufacture and use |
DE69015374T2 (de) * | 1989-01-10 | 1995-05-04 | Sumitomo Chemical Co | Dispersionsfarbstoffzubereitung zum Färben oder Bedrucken von hydrophoben Fasermaterialien. |
DE3927069A1 (de) * | 1989-08-16 | 1991-02-21 | Basf Ag | Phenonazofarbstoffe und verfahren zum thermischen transfer dieser farbstoffe |
US5550098A (en) * | 1991-11-14 | 1996-08-27 | Dai Nippon Printing Co., Ltd. | Thermal transfer sheet |
JPH08108637A (ja) * | 1994-10-13 | 1996-04-30 | Nippon Kayaku Co Ltd | 感熱転写用シート |
US5728201A (en) * | 1995-09-14 | 1998-03-17 | Canon Kabushiki Kaisha | Ink, and ink-jet recording method and instruments using the same |
US6353094B1 (en) * | 1999-03-22 | 2002-03-05 | Ciba Specialty Chemicals Corporation | Dyes, a process for their preparation and their use |
-
2002
- 2002-02-28 WO PCT/EP2002/002150 patent/WO2002072707A1/en active IP Right Grant
- 2002-02-28 MX MXPA03006339A patent/MXPA03006339A/es active IP Right Grant
- 2002-02-28 JP JP2002571768A patent/JP4380990B2/ja not_active Expired - Lifetime
- 2002-02-28 CN CNB028061977A patent/CN1288211C/zh not_active Expired - Lifetime
- 2002-02-28 EP EP02702379A patent/EP1368431B1/en not_active Expired - Lifetime
- 2002-02-28 AT AT02702379T patent/ATE380221T1/de not_active IP Right Cessation
- 2002-02-28 DE DE60223907T patent/DE60223907T2/de not_active Expired - Lifetime
- 2002-02-28 BR BR0207944-5A patent/BR0207944A/pt not_active IP Right Cessation
- 2002-02-28 CA CA002434837A patent/CA2434837A1/en not_active Abandoned
- 2002-02-28 KR KR10-2003-7011764A patent/KR20030090664A/ko not_active Application Discontinuation
- 2002-02-28 US US10/469,889 patent/US6953846B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JP2004526836A (ja) | 2004-09-02 |
ATE380221T1 (de) | 2007-12-15 |
US6953846B2 (en) | 2005-10-11 |
BR0207944A (pt) | 2004-07-27 |
MXPA03006339A (es) | 2003-10-06 |
KR20030090664A (ko) | 2003-11-28 |
EP1368431B1 (en) | 2007-12-05 |
CA2434837A1 (en) | 2002-09-19 |
US20040123403A1 (en) | 2004-07-01 |
WO2002072707A1 (en) | 2002-09-19 |
CN1288211C (zh) | 2006-12-06 |
CN1496388A (zh) | 2004-05-12 |
DE60223907T2 (de) | 2008-10-16 |
EP1368431A1 (en) | 2003-12-10 |
DE60223907D1 (de) | 2008-01-17 |
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