DE69214618D1 - Quaternär-Ammonium Tenside, Verfahren zu ihrer Herstellung, Basen und ihre ableitenden Weichmacher - Google Patents

Quaternär-Ammonium Tenside, Verfahren zu ihrer Herstellung, Basen und ihre ableitenden Weichmacher

Info

Publication number
DE69214618D1
DE69214618D1 DE69214618T DE69214618T DE69214618D1 DE 69214618 D1 DE69214618 D1 DE 69214618D1 DE 69214618 T DE69214618 T DE 69214618T DE 69214618 T DE69214618 T DE 69214618T DE 69214618 D1 DE69214618 D1 DE 69214618D1
Authority
DE
Germany
Prior art keywords
tertiary amine
quaternary ammonium
fatty acids
plasticizers
bases
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
DE69214618T
Other languages
English (en)
Other versions
DE69214618T2 (de
Inventor
Jean-Pierre Contet
Duprat Stephane Courdavault
Lionel Godefroy
Paul Nivollet
Didier Ray
Yvan Storet
Jean-Francois Vindret
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.)
Stepan Europe SAS
Original Assignee
Stepan Europe SAS
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27252553&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DE69214618(D1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from FR9116479A external-priority patent/FR2685649B1/fr
Priority claimed from FR9203199A external-priority patent/FR2688419B1/fr
Priority claimed from FR9209067A external-priority patent/FR2693665B1/fr
Application filed by Stepan Europe SAS filed Critical Stepan Europe SAS
Application granted granted Critical
Publication of DE69214618D1 publication Critical patent/DE69214618D1/de
Publication of DE69214618T2 publication Critical patent/DE69214618T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the 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
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • 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
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/38—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • 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
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16—Amines or polyamines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions
DE69214618T 1991-12-31 1992-12-31 Quaternär-Ammonium Tenside, Verfahren zu ihrer Herstellung, Basen und ihre ableitenden Weichmacher Expired - Fee Related DE69214618T2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9116479A FR2685649B1 (fr) 1991-12-31 1991-12-31 Tensioactifs a base de composes d'ammonium quaternaire, procede de preparation, bases et compositions assouplissantes derivees.
FR9203199A FR2688419B1 (fr) 1992-03-12 1992-03-12 Base tensioactive comprenant un compose cationique d'ammonium quaternaire et un compose a titre de solvant et composition assouplissante comprenant une telle base.
FR9209067A FR2693665B1 (fr) 1992-07-17 1992-07-17 Compositions tensioactives cationiques, à base de mono ou polyalkyl ester et/ou amido ammonium, et leurs procédés de préparation.

Publications (2)

Publication Number Publication Date
DE69214618D1 true DE69214618D1 (de) 1996-11-21
DE69214618T2 DE69214618T2 (de) 1997-02-20

Family

ID=27252553

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69214618T Expired - Fee Related DE69214618T2 (de) 1991-12-31 1992-12-31 Quaternär-Ammonium Tenside, Verfahren zu ihrer Herstellung, Basen und ihre ableitenden Weichmacher

Country Status (5)

Country Link
US (2) US5637743A (de)
EP (1) EP0550361B1 (de)
AT (1) ATE144245T1 (de)
DE (1) DE69214618T2 (de)
ES (1) ES2094893T3 (de)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2157178C (en) † 1993-03-01 2002-08-20 Errol Hoffman Wahl Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
DE4324395A1 (de) * 1993-07-21 1995-01-26 Henkel Kgaa Verfahren zur Herstellung von Weichspüler-Dispersionen
EP0638639B1 (de) * 1993-08-10 2000-04-12 Akzo Nobel N.V. Biologisch abbaubare Wäscheweichspülerzusammensetzung
DE69423935T2 (de) * 1993-08-10 2000-11-30 Akzo Nobel Nv Biologisch abbaubare Wäscheweichspülerzusammensetzung
ATE147719T1 (de) * 1993-09-17 1997-02-15 Stepan Europe Basische verbindung als tenside die eine quaternär ammonium verbindung und lösungsmittel umfasst, und ihre umfassende weichrachende zusammensetzung
US6559117B1 (en) 1993-12-13 2003-05-06 The Procter & Gamble Company Viscosity stable concentrated liquid fabric softener compositions
ES2144603T5 (es) * 1993-12-13 2004-11-16 THE PROCTER & GAMBLE COMPANY Composiciones liquidas concentradas, de viscosidad estable, de suavizante para materiales textiles.
DE4409322C1 (de) 1994-03-18 1995-04-06 Henkel Kgaa Verfahren zur Herstellung von Esterquats
US5869716A (en) * 1994-03-18 1999-02-09 Henkel Kommanditgesellschaft Auf Aktien Process for the production of esterquats
MA23554A1 (fr) * 1994-05-18 1995-12-31 Procter & Gamble Compositions assouplissantes pour le linge a base d'ammonium quaternaire biodegradables et concentrees contenant des composes ammonium quaternaire avec des chaines alkyle d'acide gras courtes
DE4446137A1 (de) * 1994-12-23 1996-06-27 Huels Chemische Werke Ag Quaternierte Triethanolamindifettsäureester
KR100262106B1 (ko) 1995-07-11 2000-07-15 데이비드 엠 모이어 농축된, 수-분산성의, 안정한 직물 유연 조성물
US5916863A (en) * 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
BR9709689A (pt) * 1996-06-12 1999-08-10 Akzo Nobel Nv Processo para a preparação de sais quaternários de éster de trialcanolamina
US6759383B2 (en) * 1999-12-22 2004-07-06 The Procter & Gamble Company Fabric softening compound
CA2290734A1 (en) * 1997-05-19 1998-11-26 The Procter & Gamble Company Quaternary fatty acid triethanolamine ester salts and their use as fabric softeners
DE19756434A1 (de) * 1997-12-18 1999-06-24 Witco Surfactants Gmbh Wäßrige Weichspülmittel mit verbessertem Weichgriff
DE19855366A1 (de) * 1998-12-01 2000-06-08 Witco Surfactants Gmbh Niedrigkonzentrierte, hochviskose wäßrige Weichspülmittel
DE10104033A1 (de) 2001-01-31 2002-08-14 Wella Ag Haarpflegemittel mit diquaternären Silikonpolymeren
BR0207909A (pt) * 2001-03-07 2004-07-27 Procter & Gamble Composição condicionadora de tecido adicionada ao enxágue para uso onde resìduo de detergente estiver presente
US7311853B2 (en) * 2002-09-20 2007-12-25 The Procter & Gamble Company Paper softening compositions containing quaternary ammonium compound and high levels of free amine and soft tissue paper products comprising said compositions
TW200417656A (en) * 2002-10-17 2004-09-16 Procter & Gamble Paper softening compositions containing low levels of high molecular weight polymers and soft tissue paper products comprising said compositions
US20040097395A1 (en) * 2002-11-14 2004-05-20 Andre Crutzen Fabric softening composition containing esterquat with specific ester distribution and sequestrant
US20040097396A1 (en) * 2002-11-14 2004-05-20 Myriam Peeters Concentrated fabric softening composition containing esterquat with specific ester distribution and an electrolyte
PL1664935T3 (pl) * 2003-08-19 2008-01-31 Avantor Performance Mat Inc Kompozycje do usuwania powłok oraz czyszczenia dla mikroelektroniki
US8618316B1 (en) 2004-03-05 2013-12-31 Stepan Company Low temperature ramp rate ester quat formation process
US7211556B2 (en) * 2004-04-15 2007-05-01 Colgate-Palmolive Company Fabric care composition comprising polymer encapsulated fabric or skin beneficiating ingredient
EP1964833B1 (de) * 2007-03-02 2012-08-08 Cognis IP Management GmbH Asymmetrische Kationtenside
MY151001A (en) * 2007-12-28 2014-03-31 Malaysian Palm Oil Board Mpob Fatty acid compositions of methyl ester for esterquats production suitable for fabric softener
MY151982A (en) * 2008-11-26 2014-07-31 Colgate Palmolive Co Fabric softening compositions and methods
CN102858934B (zh) * 2010-02-15 2016-03-23 斯蒂潘公司 用于生成酯胺的改善的催化剂
CN101816981B (zh) * 2010-03-16 2012-12-19 武汉理工大学 一种环境友好型胺类阳离子捕收剂及其使用方法
RU2012157095A (ru) 2010-05-28 2014-07-10 Колгейт-Палмолив Компани Насыщение цепи жирной кислоты в эстерквате на основе алканоламина
AU2011323840B2 (en) 2010-10-25 2015-09-24 Stepan Company Fatty amides and derivatives from natural oil metathesis
CA2815683C (en) 2010-10-25 2018-01-02 Dave R. Allen Esteramines and derivatives from natural oil metathesis
US20140050687A1 (en) 2011-04-28 2014-02-20 Estman Chemical Company Betaine esters and process for making and using
SG11201405008SA (en) 2012-02-21 2014-09-26 Stepan Co Fabric softener compositions
US9688944B2 (en) 2012-04-24 2017-06-27 Stepan Company Synergistic surfactant blends
KR101694599B1 (ko) * 2012-05-07 2017-01-09 에보니크 데구사 게엠베하 섬유 유연제 활성 조성물 및 그의 제조 방법
DE102012021742A1 (de) * 2012-11-06 2014-05-08 Schill + Seilacher Gmbh Zusammensetzung zur permanenten Hydrophilierung von Polyolefinfasern und deren Verwendung
CA2907078C (en) 2013-03-15 2021-06-29 Dober Chemical Corp. Dewatering compositions and methods
CN103553946A (zh) * 2013-10-14 2014-02-05 中国日用化学工业研究院 一种固体酸催化脂肪酸与乙醇胺合成酯基叔胺的方法
CN103553947B (zh) * 2013-11-05 2015-03-04 中国日用化学工业研究院 一种含羟乙基的双酯基季铵盐的制备方法
EP3489337A1 (de) * 2017-11-28 2019-05-29 The Procter & Gamble Company Weichspülerzusammensetzung mit verbesserter viskositätsstabilität
EP3814318B1 (de) 2018-06-26 2024-01-24 Evonik Operations GmbH Herstellungsverfahren für esterquats auf basis von öl

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2589674A (en) * 1947-05-24 1952-03-18 American Cyanamid Co Aliphatic amido propyl quaternary ammonium salts
US2935474A (en) * 1955-11-28 1960-05-03 Visco Products Co Process of inhibiting corrosion and corrosion inhibiting compositions
US3074815A (en) * 1961-01-23 1963-01-22 Nalco Chemical Co Treatment of cellulosic fibrous materials with diamide quaternaries and the resulting articles
US3915867A (en) * 1973-04-24 1975-10-28 Stepan Chemical Co Domestic laundry fabric softener
DE2641286A1 (de) * 1975-11-12 1977-06-02 Texaco Development Corp Quartaere ammoniumverbindung und ihre verwendung
US4128485A (en) * 1976-08-16 1978-12-05 Colgate-Palmolive Company Fabric softening compounds
DE3137043A1 (de) * 1981-09-17 1983-03-24 Bayer Ag, 5090 Leverkusen Ammoniumverbindungen
DE3325228A1 (de) * 1983-07-13 1985-01-24 Hoechst Ag, 6230 Frankfurt Veresterte, oxalkylierte quaternaere ammoniumverbindungen, verfahren zu deren herstellung und deren verwendung als faserpraeparationsmittel
DE3710064A1 (de) * 1987-03-27 1988-10-06 Hoechst Ag Verfahren zur herstellung von quaternaeren esteraminen und ihre verwendung
DE3720332A1 (de) * 1987-06-19 1988-12-29 Huels Chemische Werke Ag Verfahren zur herstellung von trialkanolamindifettsaeureestern und deren verwendung
DE4015849A1 (de) * 1990-05-17 1991-11-21 Henkel Kgaa Quaternierte ester

Also Published As

Publication number Publication date
US5637743A (en) 1997-06-10
US5750492A (en) 1998-05-12
DE69214618T2 (de) 1997-02-20
EP0550361A1 (de) 1993-07-07
EP0550361B1 (de) 1996-10-16
ES2094893T3 (es) 1997-02-01
ATE144245T1 (de) 1996-11-15

Similar Documents

Publication Publication Date Title
DE69214618T2 (de) Quaternär-Ammonium Tenside, Verfahren zu ihrer Herstellung, Basen und ihre ableitenden Weichmacher
FI871629A (fi) Segmenttipolyesteri, jossa on haarautuneita hydrofiilisiä pääteryhmiä ja sitä sisältävä detergenttikoostumus
DE3887247T2 (de) Feste unverdauliche fettähnliche Verbindungen.
EG16585A (en) Stabilized oil-in-water cleaning microemulsions.
AT389465B (de) Verfahren zur bildung von mikrokapseln oder mikromatrixkoerpern
ATE255880T1 (de) Verwendung von kokosölfettsäureacylglutamin in reinigungsmitteln
CA2021322A1 (en) Fabric softening composition
CS183091A3 (en) Cephalosporins, having in the position 3 a propenyl radical substituted byquaternary ammonium, process of their preparation, their use as medicaments andpharmaceutical compositions in which said cephalosporins are comprised
ATE89285T1 (de) Oberflaechenaktive verbindungen und verfahren zu deren herstellung.
PT91402A (pt) Processo para a preparacao de polimeros iodados de esqueleto, dextrano
WO2002038649A3 (en) Two dimensional polyamides prepared from unsaturated carboxylic acids and amines
DE59307148D1 (de) Verfahren zum Trennen von Erdölemulsionen vom Wasser-in-Öl-Typ
DE69309536D1 (de) Haarpflegemittel
DE69314865D1 (de) Kationische tensioaktive Zusammensetzungen auf der Basis von Mono- oder Polyalkylester und/oder Amide von Ammoniumverbindungen und Verfahren zu ihrer Herstellung
GB1512318A (en) Hydrophilic polyacetals
GR3007234T3 (de)
ATE190998T1 (de) Stückförmige körperreinigungsmittel
EP0316915A3 (de) Phthalsäureestermodifiziertes Organopolysiloxan und Verfahren zu seiner Herstellung
GR3005183T3 (de)
DE69015763T2 (de) Chirales reaktionsmedium für organische reaktionen.
ATE88765T1 (de) Wasserdispergierbare zusammensetzungen mit reinigender oder schuetzender wirkung auf stahlbleche und verfahren zu ihrer herstellung.
TH22181A (th) สารประกอบแอมฟิฟิลิดที่มีอย่างน้อยที่สุดหมู่ไฮโดรฟิลิด 2 หมู่ลิค 2 หมู่และอย่างน้อยที่สุดหมู่ไฮโดรโฟบิค 2 หมู่บนพื้นฐานของไดคาร์บอกซิลิคไดเอสเตอร์
KR920701124A (ko) 4차 암모늄 화합물의 제조방법
TH14322A (de)
TH17350A (th) สารผสมสำหรับทำให้นุ่มชนิดใหม่และวิธีการทำและการใช้สารดังกล่าว

Legal Events

Date Code Title Description
8363 Opposition against the patent
8339 Ceased/non-payment of the annual fee