NO328849B1 - Kationisk tverrbundet stivelse med stabil og "skreddersydd" viskositet - Google Patents
Kationisk tverrbundet stivelse med stabil og "skreddersydd" viskositet Download PDFInfo
- Publication number
- NO328849B1 NO328849B1 NO20003151A NO20003151A NO328849B1 NO 328849 B1 NO328849 B1 NO 328849B1 NO 20003151 A NO20003151 A NO 20003151A NO 20003151 A NO20003151 A NO 20003151A NO 328849 B1 NO328849 B1 NO 328849B1
- Authority
- NO
- Norway
- Prior art keywords
- cationic
- cross
- agent
- bis
- epoxypropyl
- Prior art date
Links
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 153
- 229920002472 Starch Polymers 0.000 title claims abstract description 80
- 235000019698 starch Nutrition 0.000 title claims abstract description 79
- 239000008107 starch Substances 0.000 title claims description 34
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 47
- 238000004519 manufacturing process Methods 0.000 claims abstract description 27
- 238000004132 cross linking Methods 0.000 claims abstract description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 64
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 37
- 150000003973 alkyl amines Chemical class 0.000 claims description 26
- 125000005131 dialkylammonium group Chemical group 0.000 claims description 22
- 239000003153 chemical reaction reagent Substances 0.000 claims description 19
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 14
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000005270 trialkylamine group Chemical group 0.000 claims description 8
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 7
- CSPHGSFZFWKVDL-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CCl CSPHGSFZFWKVDL-UHFFFAOYSA-M 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229920000647 polyepoxide Polymers 0.000 claims description 6
- -1 3-chloro-2-hydroxypropyl Chemical group 0.000 claims description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 5
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- UGTZMIPZNRIWHX-UHFFFAOYSA-K sodium trimetaphosphate Chemical compound [Na+].[Na+].[Na+].[O-]P1(=O)OP([O-])(=O)OP([O-])(=O)O1 UGTZMIPZNRIWHX-UHFFFAOYSA-K 0.000 claims description 3
- FLGMAMYMYDIKLE-UHFFFAOYSA-N chloro hypochlorite;phosphane Chemical compound P.ClOCl FLGMAMYMYDIKLE-UHFFFAOYSA-N 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002002 slurry Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229920001592 potato starch Polymers 0.000 description 9
- XEPXTKKIWBPAEG-UHFFFAOYSA-N 1,1-dichloropropan-1-ol Chemical compound CCC(O)(Cl)Cl XEPXTKKIWBPAEG-UHFFFAOYSA-N 0.000 description 7
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000356 contaminant Substances 0.000 description 4
- 125000005265 dialkylamine group Chemical group 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 229940051269 1,3-dichloro-2-propanol Drugs 0.000 description 3
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- LTVDFSLWFKLJDQ-UHFFFAOYSA-N α-tocopherolquinone Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 240000003183 Manihot esculenta Species 0.000 description 2
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005630 Diquat Substances 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/21—Macromolecular organic compounds of natural origin; Derivatives thereof
- D21H17/24—Polysaccharides
- D21H17/28—Starch
- D21H17/29—Starch cationic
-
- 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
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/003—Crosslinking of starch
- C08B31/006—Crosslinking of derivatives of starch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/08—Ethers
- C08B31/12—Ethers having alkyl or cycloalkyl radicals substituted by heteroatoms, e.g. hydroxyalkyl or carboxyalkyl starch
- C08B31/125—Ethers having alkyl or cycloalkyl radicals substituted by heteroatoms, e.g. hydroxyalkyl or carboxyalkyl starch having a substituent containing at least one nitrogen atom, e.g. cationic starch
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Paper (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9914275.4A GB9914275D0 (en) | 1999-06-18 | 1999-06-18 | Cationic cross-bonded starch with stable and tailor-made viscosity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20003151D0 NO20003151D0 (no) | 2000-06-16 |
| NO20003151L NO20003151L (no) | 2000-12-19 |
| NO328849B1 true NO328849B1 (no) | 2010-05-31 |
Family
ID=10855621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20003151A NO328849B1 (no) | 1999-06-18 | 2000-06-16 | Kationisk tverrbundet stivelse med stabil og "skreddersydd" viskositet |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6436237B1 (zh) |
| EP (1) | EP1061086B2 (zh) |
| CN (1) | CN1157413C (zh) |
| AT (1) | ATE291036T1 (zh) |
| DE (1) | DE60018638T3 (zh) |
| DK (1) | DK1061086T4 (zh) |
| ES (1) | ES2235784T5 (zh) |
| GB (1) | GB9914275D0 (zh) |
| ID (1) | ID26386A (zh) |
| NO (1) | NO328849B1 (zh) |
| PT (1) | PT1061086E (zh) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE44519E1 (en) | 2000-08-10 | 2013-10-08 | Cargill, Incorporated | Starch compositions and methods for use in papermaking |
| DE102007050839A1 (de) * | 2007-10-24 | 2009-04-30 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Kohlehydratbasierende Additive mit Klebeeffekt für wässrige Feuer- und Brandsschutzmittel, deren Herstellung und Verwendung |
| LT6229B (lt) | 2014-03-10 | 2015-10-26 | Kauno technologijos universitetas | Modifikuoto krakmolo flokuliantas ir jo gamybos būdas |
| CN106608919A (zh) * | 2015-10-23 | 2017-05-03 | 金东纸业（江苏）股份有限公司 | 一种阳离子淀粉的制备方法 |
| CN106243232B (zh) * | 2016-07-25 | 2019-03-26 | 山东熙来淀粉有限公司 | 一种高性能湿部添加剂及其制备方法 |
| JP7418211B2 (ja) | 2016-12-14 | 2024-01-19 | エコラブ ユーエスエイ インク | 四級カチオン性ポリマー |
| US11427964B2 (en) | 2018-06-12 | 2022-08-30 | Ecolab Usa Inc. | Quaternary cationic surfactants and polymers for use as release and coating modifying agents in creping and tissue papers |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE553544A (zh) * | ||||
| DE1189966B (de) * | 1955-12-20 | 1965-04-01 | Corn Products Company Eine Ges | Verfahren zur Herstellung von Staerkeaminoalkylaethern |
| US3778431A (en) * | 1972-10-16 | 1973-12-11 | Standard Brands Inc | Gelatinizable crosslinked cationic starch and method for its manufacture |
| US3884909A (en) * | 1973-09-24 | 1975-05-20 | Standard Brands Inc | Gelatinizable crosslinked cationic starch and method for its manufacture |
| US4066673A (en) * | 1974-02-25 | 1978-01-03 | Westvaco Corporation | Process for making quaternary amines of epichlorohydrin |
| US4029885A (en) * | 1975-12-31 | 1977-06-14 | Nalco Chemical Company | Cationic starch sizing |
| DE3103713C2 (de) * | 1981-02-04 | 1983-03-03 | Degussa Ag, 6000 Frankfurt | Verfahren zur Reinigung der bei der Herstellung von 2,3-Epoxypropyltrialkylammoniumchloriden entstehenden Umsetzungsgemische |
| US4602110A (en) * | 1985-05-15 | 1986-07-22 | The Dow Chemical Company | Method of purifying 3-chloro-2-hydroxypropyl trialkylammonium chloride |
| DE3539266A1 (de) * | 1985-11-06 | 1987-05-07 | Basf Ag | Verfahren zur herstellung von trialkylaminen |
| EP0379939B1 (en) * | 1989-01-23 | 1993-08-04 | Air Products And Chemicals, Inc. | A flexible process for the production of di and trialkylamines |
| JPH0672126B2 (ja) * | 1989-05-10 | 1994-09-14 | ダイソー株式会社 | ３―クロロ―２―ヒドロキシプロピルトリメチルアンモニウムクロライド水溶液の製造法 |
| US5122231A (en) * | 1990-06-08 | 1992-06-16 | Cargill, Incorporated | Cationic cross-linked starch for wet-end use in papermaking |
| US5077435A (en) * | 1990-09-12 | 1991-12-31 | The Dow Chemical Company | Preparation of halohydroxypropyl-trialkylammonium halides |
| US5368690A (en) * | 1992-12-23 | 1994-11-29 | National Starch And Chemical Investment Holding Corporation | Method of papermaking using crosslinked cationic/amphoteric starches |
| US5463127A (en) * | 1995-01-17 | 1995-10-31 | The Dow Chemical Company | Process for preparation of halohydroxypropyl-trialkylammonium halides |
| RU2111957C1 (ru) * | 1995-03-23 | 1998-05-27 | Акционерное общество закрытого типа "Урал-АС" | Способ получения 3-хлоро-2-гидроксипропилтриметиламмонийхлорида |
| AUPO017196A0 (en) * | 1996-05-30 | 1996-06-27 | George Weston Foods Limited | Novel wet end processing aid |
| FI970422A0 (fi) * | 1997-01-31 | 1997-01-31 | Raisio Chem Oy | Foerfarande foer limning av papper |
-
1999
- 1999-06-18 GB GBGB9914275.4A patent/GB9914275D0/en not_active Ceased
-
2000
- 2000-06-01 PT PT00304687T patent/PT1061086E/pt unknown
- 2000-06-01 EP EP00304687A patent/EP1061086B2/en not_active Expired - Lifetime
- 2000-06-01 DE DE60018638T patent/DE60018638T3/de not_active Expired - Lifetime
- 2000-06-01 DK DK00304687T patent/DK1061086T4/da active
- 2000-06-01 ES ES00304687T patent/ES2235784T5/es not_active Expired - Lifetime
- 2000-06-01 AT AT00304687T patent/ATE291036T1/de active
- 2000-06-06 US US09/588,614 patent/US6436237B1/en not_active Expired - Lifetime
- 2000-06-16 ID IDP20000496D patent/ID26386A/id unknown
- 2000-06-16 CN CNB001186280A patent/CN1157413C/zh not_active Expired - Fee Related
- 2000-06-16 NO NO20003151A patent/NO328849B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60018638T3 (de) | 2008-11-13 |
| ES2235784T5 (es) | 2008-12-01 |
| EP1061086A1 (en) | 2000-12-20 |
| NO20003151L (no) | 2000-12-19 |
| CN1157413C (zh) | 2004-07-14 |
| EP1061086B1 (en) | 2005-03-16 |
| ES2235784T3 (es) | 2005-07-16 |
| DK1061086T3 (da) | 2005-05-23 |
| DE60018638D1 (de) | 2005-04-21 |
| ATE291036T1 (de) | 2005-04-15 |
| NO20003151D0 (no) | 2000-06-16 |
| US6436237B1 (en) | 2002-08-20 |
| DE60018638T2 (de) | 2005-08-04 |
| GB9914275D0 (en) | 1999-08-18 |
| EP1061086B2 (en) | 2008-08-13 |
| DK1061086T4 (da) | 2008-12-01 |
| CN1278533A (zh) | 2001-01-03 |
| ID26386A (id) | 2000-12-21 |
| PT1061086E (pt) | 2005-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |