KR100927810B1 - 피롤로[3,4-ｃ]피롤의 직접 제조방법 - Google Patents

피롤로[3,4-ｃ]피롤의 직접 제조방법 Download PDF

Info

Publication number
KR100927810B1
KR100927810B1 KR1020047003651A KR20047003651A KR100927810B1 KR 100927810 B1 KR100927810 B1 KR 100927810B1 KR 1020047003651 A KR1020047003651 A KR 1020047003651A KR 20047003651 A KR20047003651 A KR 20047003651A KR 100927810 B1 KR100927810 B1 KR 100927810B1
Authority
KR
South Korea
Prior art keywords
formula
alkyl
hydrogen
branched
straight
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.)
Expired - Lifetime
Application number
KR1020047003651A
Other languages
English (en)
Korean (ko)
Other versions
KR20040029479A (ko
Inventor
루피욱스빈센트
모도욱스플로렌체
Original Assignee
시바 홀딩 인크
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 시바 홀딩 인크 filed Critical 시바 홀딩 인크
Publication of KR20040029479A publication Critical patent/KR20040029479A/ko
Application granted granted Critical
Publication of KR100927810B1 publication Critical patent/KR100927810B1/ko
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/004—Diketopyrrolopyrrole dyes
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C09B67/0039—Mixtures of diketopyrrolopyrroles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Paints Or Removers (AREA)
  • Cosmetics (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Electroluminescent Light Sources (AREA)
KR1020047003651A 2001-09-11 2002-09-03 피롤로[3,4-ｃ]피롤의 직접 제조방법 Expired - Lifetime KR100927810B1 (ko)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
EP01810875.3 2001-09-11
EP01810875 2001-09-11
EP01811249 2001-12-20
EP01811249.0 2001-12-20
EP02405223 2002-03-22
EP02405223.5 2002-03-22
PCT/EP2002/009791 WO2003022847A2 (en) 2001-09-11 2002-09-03 Process for the direct preparation of pyrrolo[3,4-c]pyrroles

Publications (2)

Publication Number Publication Date
KR20040029479A KR20040029479A (ko) 2004-04-06
KR100927810B1 true KR100927810B1 (ko) 2009-11-23

Family

ID=27224407

Family Applications (2)

Application Number Title Priority Date Filing Date
KR1020047003651A Expired - Lifetime KR100927810B1 (ko) 2001-09-11 2002-09-03 피롤로[3,4-ｃ]피롤의 직접 제조방법
KR10-2004-7003647A Withdrawn KR20040029478A (ko) 2001-09-11 2002-09-03 디케토피롤로피롤의 제조방법

Family Applications After (1)

Application Number Title Priority Date Filing Date
KR10-2004-7003647A Withdrawn KR20040029478A (ko) 2001-09-11 2002-09-03 디케토피롤로피롤의 제조방법

Country Status (13)

Country Link
US (3) US7326793B2 (enExample)
EP (2) EP1425282B1 (enExample)
JP (3) JP4707951B2 (enExample)
KR (2) KR100927810B1 (enExample)
CN (2) CN1553913B (enExample)
AT (2) ATE357446T1 (enExample)
AU (2) AU2002340851A1 (enExample)
CA (1) CA2457710A1 (enExample)
DE (2) DE60210120T2 (enExample)
DK (1) DK1436296T3 (enExample)
MX (1) MXPA04002334A (enExample)
WO (2) WO2003022847A2 (enExample)
ZA (1) ZA200401106B (enExample)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003002672A2 (en) * 2001-06-29 2003-01-09 Ciba Specialty Chemicals Holding Inc. Fluorescent diketopyrrolopyrroles
ATE357446T1 (de) * 2001-09-11 2007-04-15 Ciba Sc Holding Ag Verfahren zur herstellung von diketopyrrolopyrrolen
US7442804B2 (en) 2003-07-07 2008-10-28 Ciba Specialty Chemicals Corporation Process for the preparation of furopyrroles
CA2542519A1 (en) 2003-10-23 2005-05-06 Ciba Specialty Chemicals Holding Inc. Heat-stable diketopyrrolopyrrole pigment mixtures
WO2008030115A2 (en) * 2006-09-06 2008-03-13 Elena Korchagina Fluorescent cell markers
JP4986451B2 (ja) * 2005-06-30 2012-07-25 信一郎 礒部 マーキング剤
JP4214493B2 (ja) 2006-07-20 2009-01-28 Ｄｉｃ株式会社 高彩度ｃ．ｉ．ピグメントレッド２５４及びその製造方法
DE102007011068A1 (de) * 2007-03-07 2008-09-11 Clariant International Ltd. Verfahren zur direkten Herstellung feinteiliger Diketopyrrolopyrrolpigmente
JP5497991B2 (ja) * 2008-03-13 2014-05-21 富士フイルム株式会社 顔料微粒子の製造方法
JP5268410B2 (ja) * 2008-04-11 2013-08-21 富士フイルム株式会社 顔料分散組成物、顔料分散組成物の製造方法、着色重合性組成物、カラーフィルタ、及びカラーフィルタの製造方法
EP2350161B1 (en) 2008-10-31 2018-11-21 Basf Se Diketopyrrolopyrrole polymers for use in organic field effect transistors
WO2010136353A1 (en) 2009-05-27 2010-12-02 Basf Se Diketopyrrolopyrrole polymers for use in organic semiconductor devices
JP5629067B2 (ja) * 2009-08-18 2014-11-19 富士フイルム株式会社 顔料微粒子分散体、これを用いたカラーフィルタ、及び顔料微粒子分散体の製造方法、並びに顔料誘導体化合物
WO2011054731A1 (en) 2009-11-05 2011-05-12 Basf Se Fluorescent materials
KR101222552B1 (ko) * 2010-03-25 2013-01-16 경북대학교 산학협력단 컬러필터용 고내열성 ｄｐｐ계 염료 및 그 제조방법
CN101831197A (zh) * 2010-05-17 2010-09-15 南通市争妍颜料化工有限公司 颜料红254的高遮盖力品种hl的生产工艺
CN102892807A (zh) 2010-05-19 2013-01-23 巴斯夫欧洲公司 用于有机半导体器件的二酮基吡咯并吡咯聚合物
WO2012017005A2 (en) 2010-08-05 2012-02-09 Basf Se Polymers based on benzodiones
GB201200184D0 (en) * 2012-01-06 2012-02-22 Johnson Matthey Plc Tracers and method of marking liquids
CN103012409B (zh) * 2012-12-07 2015-05-27 辽宁鸿港化工有限公司 制备吡咯并吡咯-1,4-二酮衍生物的改进方法
WO2014181763A1 (ja) * 2013-05-07 2014-11-13 山本化成株式会社 感熱発色性組成物及び該組成物を用いてなる感熱記録材料
CN110791116A (zh) * 2018-08-01 2020-02-14 浙江浩川科技有限公司 一种含碳碳双键的dpp类有机颜料及合成方法和用途
CN110791117A (zh) * 2018-08-01 2020-02-14 浙江浩川科技有限公司 一种芳香亚胺基取代的dpp类有机颜料及合成方法和用途
CN110693754B (zh) * 2019-11-16 2022-08-23 烟台东方化学有限公司 一种抗菌消炎的吡啶酮组合物及包含其的化妆品
CN116813625A (zh) * 2023-06-29 2023-09-29 贵州民族大学 一种具有高荧光量子产率的吡咯并吡咯二酮有机染料及其制备方法
CN116969952A (zh) * 2023-07-31 2023-10-31 山东凯瑞尔光电科技有限公司 一种二苯基吡咯并吡咯二酮衍生物及其颜料组合物

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5738719A (en) * 1995-06-15 1998-04-14 Ciba Specialty Chemicals Corporation Pigment compositions of diketopyrrolopyrroles
US6057449A (en) * 1998-06-02 2000-05-02 Ciba Specialty Chemicals Corporation Direct preparation of pyrrolo[3,4-c]pyrroles

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3366011D1 (en) 1982-05-17 1986-10-16 Ciba Geigy Ag Preparation of pyrrolo-(3,4-c) pyrroles
CS236794B2 (cs) * 1982-05-17 1985-05-15 Ciba Geigy Ag Způsob přípravy l,4-diketopyrrolo[3,4-c]pyrrolu
US4585878A (en) * 1983-06-29 1986-04-29 Ciba-Geigy Corporation N-substituted 1,4-diketopyrrolo-[3,4-c]-pyrroles
US4783540A (en) * 1986-08-07 1988-11-08 Ciba-Geigy Corporation Solid solutions of pyrrolo-(3,4-C)-pyrrols
DE3713459A1 (de) * 1987-02-05 1988-08-18 Langhals Heinz Lichtechte, leichtloesliche diketopyrrolopyrrol-fluoreszenzfarbstoffe
EP0426717B1 (de) * 1988-07-29 1996-04-24 Riedel-De Haen Aktiengesellschaft Optische datenspeicher
EP0511165B1 (de) 1991-04-26 1996-08-14 Ciba-Geigy Ag Neue Diketopyrrolopyrrolverbindungen
US5424157A (en) 1992-12-01 1995-06-13 Mita Industrial Co., Ltd. Electrophotosensitive material containing disazo compound as charge-generating agent
TW372244B (en) 1993-07-29 1999-10-21 Ciba Sc Holding Ag Process for producing novel finely divided highly transparent diketopyrrolopyrrole pigments
JP2999669B2 (ja) 1993-08-24 2000-01-17 株式会社三和化学研究所 ベンゾ［ｂ］フランカルボキサミド誘導体、その製法及び用途
EP0690059B1 (de) * 1994-06-29 1999-09-08 Ciba SC Holding AG Zwei neue Kristallmodifikationen eines Diketopyrrolopyrrolpigments
GB9418499D0 (en) * 1994-09-14 1994-11-02 Ciba Geigy Ag Process for producing n-methylated organic pigments
JP3704748B2 (ja) * 1995-06-23 2005-10-12 東洋インキ製造株式会社 有機エレクトロルミネッセンス素子用電子輸送材料およびそれを用いた有機エレクトロルミネッセンス素子
DE59707889D1 (de) * 1996-01-30 2002-09-12 Ciba Sc Holding Ag Polymerisierbare Diketopyrrolopyrrole und damit hergestellte Polymere
DE59804631D1 (de) 1997-05-06 2002-08-08 Ciba Sc Holding Ag Diketopyrrolopyrrolzusammensetzungen
TW503255B (en) * 1999-09-27 2002-09-21 Ciba Sc Holding Ag Electroluminescent devices comprising diketopyrrolopyrroles
EP1329493A3 (en) 1999-09-27 2007-05-23 Ciba SC Holding AG Electroluminescent devices comprising diketopyrrolopyrroles
EP1087005B1 (en) * 1999-09-27 2004-02-25 Ciba SC Holding AG Fluorescent diketopyrrolopyrroles
US20010015154A1 (en) * 2000-01-27 2001-08-23 Roman Lenz Ternary pigment compositions
JP4785222B2 (ja) * 2000-02-09 2011-10-05 東洋インキＳｃホールディングス株式会社 カラーフィルタ用顔料およびその製造方法、それを用いたカラーフィルタ用着色組成物ならびにカラーフィルタ
DE10028104A1 (de) * 2000-06-07 2001-12-13 Clariant Gmbh Verfahren zur Herstellung von Diketopyrrologyrrol-Pigmenten
JP2003059670A (ja) * 2001-06-08 2003-02-28 Toray Ind Inc 発光素子
JP2004537638A (ja) 2001-08-10 2004-12-16 チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド 蛍光性ジケトピロロピロール類似体
ATE357446T1 (de) * 2001-09-11 2007-04-15 Ciba Sc Holding Ag Verfahren zur herstellung von diketopyrrolopyrrolen

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5738719A (en) * 1995-06-15 1998-04-14 Ciba Specialty Chemicals Corporation Pigment compositions of diketopyrrolopyrroles
US6057449A (en) * 1998-06-02 2000-05-02 Ciba Specialty Chemicals Corporation Direct preparation of pyrrolo[3,4-c]pyrroles

Also Published As

Publication number Publication date
DE60219037D1 (de) 2007-05-03
AU2002340851A1 (en) 2003-03-24
JP2010222368A (ja) 2010-10-07
DE60219037T8 (de) 2008-04-03
EP1436296A2 (en) 2004-07-14
KR20040029478A (ko) 2004-04-06
WO2003022847A2 (en) 2003-03-20
EP1425282B1 (en) 2007-03-21
DK1436296T3 (da) 2006-07-17
JP4707951B2 (ja) 2011-06-22
US20040249162A1 (en) 2004-12-09
CN1553912A (zh) 2004-12-08
DE60210120D1 (de) 2006-05-11
WO2003022848A3 (en) 2003-09-18
CA2457710A1 (en) 2003-03-20
KR20040029479A (ko) 2004-04-06
WO2003022848A2 (en) 2003-03-20
AU2002342633A1 (en) 2003-03-24
US7186847B2 (en) 2007-03-06
DE60210120T2 (de) 2006-08-17
JP5345975B2 (ja) 2013-11-20
US7326793B2 (en) 2008-02-05
ATE321049T1 (de) 2006-04-15
CN1553913B (zh) 2011-10-05
US20070117889A1 (en) 2007-05-24
ZA200401106B (en) 2004-10-19
JP2005512960A (ja) 2005-05-12
JP2005508903A (ja) 2005-04-07
JP4640913B2 (ja) 2011-03-02
US20040171847A1 (en) 2004-09-02
MXPA04002334A (es) 2004-06-29
DE60219037T2 (de) 2007-12-13
EP1436296B1 (en) 2006-03-22
WO2003022847A3 (en) 2003-09-25
EP1425282A2 (en) 2004-06-09
ATE357446T1 (de) 2007-04-15
CN1553913A (zh) 2004-12-08
US8883889B2 (en) 2014-11-11

Similar Documents

Publication Publication Date Title
KR100927810B1 (ko) 피롤로[3,4-ｃ]피롤의 직접 제조방법
EP0962499B1 (en) Direct preparation of pigmentary pyrrolo-(3,4-C)pyrroles
US4931566A (en) Process for the preparation of pyrrolo[3,4-c]pyrroles
EP1399514B1 (en) Fluorescent diketopyrrolopyrroles
US6036766A (en) Mixed crystals and solid solutions of 1,4-diketopyrrolopyrroles
KR100354289B1 (ko) 미립상시아노-치환된디케토피롤로피롤안료및이의제조방법
US20040173777A1 (en) Fluorescent diketopyrrolopyrrole analogues
MXPA99005087A (en) Direct preparation of pirrolo [3,4-c] pirro

Legal Events

Date Code Title Description
PA0105 International application

St.27 status event code: A-0-1-A10-A15-nap-PA0105

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

R17-X000 Change to representative recorded

St.27 status event code: A-3-3-R10-R17-oth-X000

R17-X000 Change to representative recorded

St.27 status event code: A-3-3-R10-R17-oth-X000

R17-X000 Change to representative recorded

St.27 status event code: A-3-3-R10-R17-oth-X000

A201 Request for examination
AMND Amendment
P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

R18-X000 Changes to party contact information recorded

St.27 status event code: A-3-3-R10-R18-oth-X000

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

AMND Amendment
E13-X000 Pre-grant limitation requested

St.27 status event code: A-2-3-E10-E13-lim-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

E601 Decision to refuse application
PE0601 Decision on rejection of patent

St.27 status event code: N-2-6-B10-B15-exm-PE0601

J201 Request for trial against refusal decision
PJ0201 Trial against decision of rejection

St.27 status event code: A-3-3-V10-V11-apl-PJ0201

AMND Amendment
P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PB0901 Examination by re-examination before a trial

St.27 status event code: A-6-3-E10-E12-rex-PB0901

B701 Decision to grant
PB0701 Decision of registration after re-examination before a trial

St.27 status event code: A-3-4-F10-F13-rex-PB0701

GRNT Written decision to grant
PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U12-oth-PR1002

Fee payment year number: 1

PG1601 Publication of registration

St.27 status event code: A-4-4-Q10-Q13-nap-PG1601

FPAY Annual fee payment

Payment date: 20121026

Year of fee payment: 4

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 4

FPAY Annual fee payment

Payment date: 20131028

Year of fee payment: 5

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 5

FPAY Annual fee payment

Payment date: 20141027

Year of fee payment: 6

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 6

FPAY Annual fee payment

Payment date: 20151103

Year of fee payment: 7

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 7

FPAY Annual fee payment

Payment date: 20161102

Year of fee payment: 8

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 8

FPAY Annual fee payment

Payment date: 20171025

Year of fee payment: 9

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 9

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 10

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 11

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 12

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 13

PC1801 Expiration of term

St.27 status event code: N-4-6-H10-H14-oth-PC1801

Not in force date: 20220904

Ip right cessation event data comment text: Termination Category : EXPIRATION_OF_DURATION