CN101108861B - 具有氰基硼酸根阴离子的盐 - Google Patents

具有氰基硼酸根阴离子的盐 Download PDF

Info

Publication number
CN101108861B
CN101108861B CN2007101361295A CN200710136129A CN101108861B CN 101108861 B CN101108861 B CN 101108861B CN 2007101361295 A CN2007101361295 A CN 2007101361295A CN 200710136129 A CN200710136129 A CN 200710136129A CN 101108861 B CN101108861 B CN 101108861B
Authority
CN
China
Prior art keywords
milliliters
alkali metal
reaction
salt
nmr
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 - Fee Related
Application number
CN2007101361295A
Other languages
English (en)
Chinese (zh)
Other versions
CN101108861A (zh
Inventor
U·韦尔茨-比尔曼
N·伊格纳特耶夫
E·伯恩哈德特
M·芬泽
H·维尔纳
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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 Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of CN101108861A publication Critical patent/CN101108861A/zh
Application granted granted Critical
Publication of CN101108861B publication Critical patent/CN101108861B/zh
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/64—Quaternary ammonium compounds having quaternised nitrogen atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
CN2007101361295A 2003-02-14 2004-01-15 具有氰基硼酸根阴离子的盐 Expired - Fee Related CN101108861B (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10306617.9 2003-02-14
DE10306617A DE10306617A1 (de) 2003-02-14 2003-02-14 Salze mit Cyanoborat-Anionen

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CNB2004800041330A Division CN100361997C (zh) 2003-02-14 2004-01-15 具有氰基硼酸根阴离子的盐

Publications (2)

Publication Number Publication Date
CN101108861A CN101108861A (zh) 2008-01-23
CN101108861B true CN101108861B (zh) 2010-06-16

Family

ID=32747947

Family Applications (3)

Application Number Title Priority Date Filing Date
CN2007101361295A Expired - Fee Related CN101108861B (zh) 2003-02-14 2004-01-15 具有氰基硼酸根阴离子的盐
CNB2007101361308A Expired - Fee Related CN100572385C (zh) 2003-02-14 2004-01-15 具有氰基硼酸根阴离子的盐
CNB2004800041330A Expired - Fee Related CN100361997C (zh) 2003-02-14 2004-01-15 具有氰基硼酸根阴离子的盐

Family Applications After (2)

Application Number Title Priority Date Filing Date
CNB2007101361308A Expired - Fee Related CN100572385C (zh) 2003-02-14 2004-01-15 具有氰基硼酸根阴离子的盐
CNB2004800041330A Expired - Fee Related CN100361997C (zh) 2003-02-14 2004-01-15 具有氰基硼酸根阴离子的盐

Country Status (11)

Country Link
US (1) US7645434B2 (https=)
EP (3) EP1726594B1 (https=)
JP (1) JP4718438B2 (https=)
KR (4) KR20110110873A (https=)
CN (3) CN101108861B (https=)
AT (3) ATE368045T1 (https=)
CA (2) CA2771069C (https=)
DE (4) DE10306617A1 (https=)
ES (1) ES2271837T3 (https=)
RU (1) RU2337912C2 (https=)
WO (1) WO2004072089A1 (https=)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7939644B2 (en) * 2003-08-21 2011-05-10 Merck Patent Gmbh Cyanoborate, fluoroalkylphosphate, fluoroalkylborate or imide dyes
GB0407908D0 (en) * 2004-04-07 2004-05-12 Univ York Ionic liquids
DE102004051278A1 (de) * 2004-10-21 2006-04-27 Merck Patent Gmbh Neue borhaltige starke Säuren, deren Herstellung und Verwendung
EP1819005A1 (en) * 2006-02-13 2007-08-15 Ecole Polytechnique Fédérale de Lausanne (EPFL) Ionic liquid electrolyte
JP4652359B2 (ja) * 2007-03-09 2011-03-16 日本合成化学工業株式会社 イオン液体の分解処理方法
CN102046599B (zh) 2008-05-26 2013-08-21 默克专利股份公司 具有四氰基硼酸根阴离子的离子液体作为溶剂用于从水溶液中萃取醇的应用
JP5583899B2 (ja) * 2008-06-04 2014-09-03 株式会社日本触媒 イオン性化合物の製造方法
EP2327707A4 (en) * 2008-08-22 2012-05-30 Nippon Catalytic Chem Ind IONIC CONNECTION, MANUFACTURING METHOD AND ION-LEADING MATERIAL THEREFOR
DE102008048015A1 (de) 2008-09-19 2010-03-25 Studiengesellschaft Kohle Mbh Verfahren zur Herstellung von Alkalimetallcyanoborat
AU2010209972B9 (en) 2009-02-02 2013-10-17 Lonza Ltd Novel tricyanoborates
DE102009037300A1 (de) 2009-08-14 2011-02-17 Merck Patent Gmbh Tetracyanoborate als Schmierstoffe
EP2526104A1 (en) * 2010-01-18 2012-11-28 Merck Patent GmbH Electrolyte formulations
EP2526107A1 (de) 2010-01-18 2012-11-28 Merck Patent GmbH Verfahren zur herstellung von perfluoralkylcyano- oder perfluoralkylcyanofluorboraten
CN102712659B (zh) * 2010-01-18 2015-09-30 默克专利有限公司 电解质配制剂
JP5595294B2 (ja) * 2010-01-22 2014-09-24 株式会社日本触媒 蓄電デバイスの電解液用添加剤およびこれを含む電解液
AP3517A (en) * 2010-04-22 2016-01-11 Genesis Lab Inc Compositions and methods for control of sand flies and other blood sucking insects.
EP2388853A1 (en) 2010-05-20 2011-11-23 Fundacion Cidetec Ionic liquid based electrolytes containing sulfide/polysulfide redox couple and uses thereof
EP2621934A1 (en) * 2010-09-28 2013-08-07 Merck Patent GmbH Electrolyte formulations containing cyano-alkoxy-borate anions
JP6038796B2 (ja) 2010-09-30 2016-12-07 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ 電解質配合物
CN103384687A (zh) 2010-11-30 2013-11-06 默克专利有限公司 电泳显示器用粒子
JP6025741B2 (ja) 2010-12-08 2016-11-16 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ 色素増感太陽電池のための添加剤
US9466431B2 (en) 2011-01-21 2016-10-11 Nippon Shokubai Co., Ltd. Ionic compound and process for production thereof, and electrolytic solution and electrical storage device each utilizing the ionic compound
EP2714698B1 (en) * 2011-05-31 2016-11-09 Merck Patent GmbH Compounds containing hydrido-tricyano-borate anions
DE102011103754A1 (de) * 2011-05-31 2012-12-06 Merck Patent Gmbh Verfahren zur Herstellung von Dihydridodicyanoborat-Salzen
KR20140039242A (ko) 2011-05-31 2014-04-01 메르크 파텐트 게엠베하 전해질 제형
US9558894B2 (en) 2011-07-08 2017-01-31 Fastcap Systems Corporation Advanced electrolyte systems and their use in energy storage devices
WO2013009720A2 (en) 2011-07-08 2013-01-17 Fastcap Systems Corporation High temperature energy storage device
CN103687863B9 (zh) * 2011-07-15 2016-07-27 默克专利有限公司 含有烷基-氰基-硼酸根或烷基-氰基-氟硼酸根阴离子的化合物
WO2013026563A1 (en) 2011-08-25 2013-02-28 Merck Patent Gmbh Additives for dye-sensitized solar cells
JP5813472B2 (ja) * 2011-09-06 2015-11-17 株式会社日本触媒 テトラシアノボレート塩の製造方法
EP2623457A1 (en) 2012-02-02 2013-08-07 VTU Holding GmbH Use of an ionic liquid for storing hydrogen
KR102093832B1 (ko) 2012-02-08 2020-03-26 메르크 파텐트 게엠베하 전도성 첨가제를 포함하는 반응성 메소겐 제제
WO2014029833A1 (en) * 2012-08-24 2014-02-27 Lonza Ltd Method for the preparation of tetraalkylammonium or tetraalkylphosphonium|tricyanidofluoroborates
WO2014029834A1 (en) * 2012-08-24 2014-02-27 Lonza Ltd Method for the preparation of tetraalkylammonium tetracyanidoborates
US9269958B2 (en) * 2012-12-07 2016-02-23 Samsung Electronics Co., Ltd. Cathode and all-solid battery including the same
EP2772495A1 (en) * 2013-03-01 2014-09-03 Lonza Ltd Method for preparation of tricyanidofluoroborates in 2 steps
DE102013009959A1 (de) 2013-06-14 2014-12-31 Julius-Maximilians-Universität Würzburg Verfahren zur Herstellung von Salzen mit Hydridocyanoborat-Anionen
DE102013013502A1 (de) * 2013-08-16 2015-03-12 Julius-Maximilians-Universität Würzburg Hexacyanodiborate
US10872737B2 (en) 2013-10-09 2020-12-22 Fastcap Systems Corporation Advanced electrolytes for high temperature energy storage device
JP2015103288A (ja) 2013-11-21 2015-06-04 ソニー株式会社 二次電池、電池パック、電動車両および電力貯蔵システム
WO2015186568A1 (ja) * 2014-06-04 2015-12-10 株式会社トクヤマ 非水電解液およびそれを用いた蓄電デバイス
DE102014008130A1 (de) 2014-06-06 2015-12-17 Julius-Maximilians-Universität Würzburg Verfahren zur Herstellung von Tetracyanoboratsalzen
DE102014014967A1 (de) * 2014-10-14 2016-04-14 Julius-Maximilians-Universität Würzburg Verfahren zur Herstellung von Verbindungen mit Monofluorotricyanoborat-Anionen
KR102668693B1 (ko) 2015-01-27 2024-05-27 패스트캡 시스템즈 코포레이션 넓은 온도 범위 울트라커패시터
DE102016001344A1 (de) 2015-09-10 2017-03-16 Julius-Maximilians-Universität Würzburg Verfahren zur Herstellung von Kaliummonofluorotricyanoborat
WO2017051923A1 (ja) 2015-09-25 2017-03-30 日本化薬株式会社 アゾ化合物、インク組成物、インクジェット記録方法及び着色体
DE102015016400A1 (de) 2015-12-18 2017-06-22 Julius-Maximilians-Universität Würzburg Verfahren zur Herstellung von Salzen mit Perfluoralkyltricyanoboratanionen oder Tetracyanoboratanionen
DE102015016401A1 (de) 2015-12-18 2017-06-22 Julius-Maximilians-Universität Würzburg Verfahren zur Herstellung von Salzen mit Monofluorotricyanoboratanionen
DE102016009846A1 (de) 2016-08-16 2018-02-22 Julius-Maximilians-Universität Würzburg Fluoralkylhydrido- und Fluoralkylcyanohydridoborate
EP3549148B1 (en) 2016-12-02 2025-01-01 Fastcap Systems Corporation Composite electrode
JP2021141101A (ja) * 2020-03-02 2021-09-16 日清紡ホールディングス株式会社 蓄電デバイス用電解液およびイオン液体
CN115477308B (zh) * 2022-08-28 2023-05-02 兰州理工大学 一种一步法常温制备四氟硼酸钠的方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4301129A (en) * 1978-09-18 1981-11-17 Thiokol Corporation Synthesis of NaBH3 CN and related compounds

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5542292A (en) 1978-09-18 1980-03-25 Thiokol Chemical Corp Method of synthesizing nabh3cn and related compounds
JPH07116113B2 (ja) 1987-05-14 1995-12-13 三菱化学株式会社 四級アンモニウム無機酸塩の製造方法
US4892944A (en) 1987-05-13 1990-01-09 Mitsubishi Petrochemical Co., Ltd. Process for producing quaternary salts
DE10055811A1 (de) * 2000-11-10 2002-05-29 Merck Patent Gmbh Tetrakisfluoroalkylborat-Salze und deren Verwendung als Leitsalze
TWI263235B (en) 2002-04-02 2006-10-01 Nippon Catalytic Chem Ind Material for electrolytic solutions and use thereof
JP4467247B2 (ja) 2002-04-02 2010-05-26 株式会社日本触媒 新規溶融塩を用いたイオン伝導体
JP4127788B2 (ja) * 2002-11-22 2008-07-30 株式会社トクヤマ オニウム塩

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4301129A (en) * 1978-09-18 1981-11-17 Thiokol Corporation Synthesis of NaBH3 CN and related compounds

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Darrick Williams et al.."Synthesis of LiBC4N4, BC3N3, and Related C-N Compoundsof Boron: New Precursors to Light Element Ceramics".J. Am. Chem. Soc.122 32.2000,122(32),7735-7741.
Darrick Williams et al.."Synthesis of LiBC4N4,BC3N3,and Related C-N Compoundsof Boron: New Precursors to Light Element Ceramics".J.Am.Chem. Soc.122 32.2000,122(32),7735-7741. *

Also Published As

Publication number Publication date
RU2005128348A (ru) 2006-04-10
US7645434B2 (en) 2010-01-12
DE502004001603D1 (de) 2006-11-09
CN101108861A (zh) 2008-01-23
JP2006517546A (ja) 2006-07-27
CA2515856C (en) 2013-05-14
ATE340799T1 (de) 2006-10-15
EP1592696A1 (de) 2005-11-09
EP1726594A1 (de) 2006-11-29
ES2271837T3 (es) 2007-04-16
EP1726594B1 (de) 2007-07-25
KR20100130645A (ko) 2010-12-13
ATE368044T1 (de) 2007-08-15
DE502004004471D1 (de) 2007-09-06
ATE368045T1 (de) 2007-08-15
CN1751053A (zh) 2006-03-22
CA2771069C (en) 2012-09-18
EP1726593A1 (de) 2006-11-29
US20060222584A1 (en) 2006-10-05
RU2337912C2 (ru) 2008-11-10
WO2004072089A1 (de) 2004-08-26
EP1726593B1 (de) 2007-07-25
JP4718438B2 (ja) 2011-07-06
KR20120081640A (ko) 2012-07-19
CA2771069A1 (en) 2004-08-26
CN100572385C (zh) 2009-12-23
DE10306617A1 (de) 2004-08-26
CN100361997C (zh) 2008-01-16
KR20110110873A (ko) 2011-10-07
KR101287689B1 (ko) 2013-07-24
KR20050100685A (ko) 2005-10-19
DE502004004472D1 (de) 2007-09-06
KR101105618B1 (ko) 2012-01-18
KR101010558B1 (ko) 2011-01-24
EP1592696B1 (de) 2006-09-27
CN101108759A (zh) 2008-01-23
CA2515856A1 (en) 2004-08-26

Similar Documents

Publication Publication Date Title
CN101108861B (zh) 具有氰基硼酸根阴离子的盐
CN110407184B (zh) 一种双氟磺酰亚胺碱金属盐的制备方法
Gais et al. About the Li⊕ Gegenion Effect on α‐Sulfonyl Carbanions
Zou et al. Two new polyoxometalates-based hybrids firstly synthesized in the ionic liquids
Naoufal et al. Replacement of the nitrogen of [1-N2B10H9]− by amines or nitriles, a route to hydrophobic monoanions
RU2351601C2 (ru) Ионные жидкости, содержащие анионы [n(cf3)2]-
Starobrat et al. Salts of highly fluorinated weakly coordinating anions as versatile precursors towards hydrogen storage materials
Ribbeck et al. Hydroxytricyanoborate Anion: Synthetic Aspects and Structural, Chemical, and Spectroscopic Properties
Bowsher et al. Use of alkali-and alkaline-earth-metal ions in the template synthesis of 12-crown-4, 15-crown-5, and 18-crown-6
Miller Cyclic borane derivatives of amino acids
US5473065A (en) Fluorinated diazabicycloalkane derivatives
WO2023240266A9 (en) Boron cluster weakly-coordinating anions and related materials
Naiini et al. Alkali and alkaline earth metal chloride complexes of triethanolamine: the structure of [Sr (TEA) 2] Cl2
EP2240498B1 (en) Production of lithium diphenylphosphide
LU502728B1 (en) Preparation Method of Halogen-free Imidazolium Hydroxide
Maksimov et al. Structure and properties of H8 (PW11TiO39) 2O heteropoly acid
Millikan et al. The alleged dipyridinium Fe (III) pentachloride and some related compounds
O'Brien et al. Some reactions of (fluoroimido) tetrafluorosulfur
Winter Investigation of Highly Lewis Acidic Gold (III) Compounds Containing Fluorido and Pentafluoroorthotellurato Ligands
Dietzel et al. Dimeric Sandwich‐like Ion Pairs in the Crystal Structure of Tetrabutylammonium Ozonide Ammoniate
Singh et al. Pyridinidm Hexafluorotitanate and its Derivatives
Besheesh Studies of N-Fluoro-Compounds

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20100616

Termination date: 20170115

CF01 Termination of patent right due to non-payment of annual fee