DE3020341C2 - - Google Patents
Info
- Publication number
- DE3020341C2 DE3020341C2 DE3020341A DE3020341A DE3020341C2 DE 3020341 C2 DE3020341 C2 DE 3020341C2 DE 3020341 A DE3020341 A DE 3020341A DE 3020341 A DE3020341 A DE 3020341A DE 3020341 C2 DE3020341 C2 DE 3020341C2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- oxide
- alkylene oxide
- alcohol
- tris
- 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
Links
- 239000003054 catalyst Substances 0.000 claims description 32
- 229920005862 polyol Polymers 0.000 claims description 25
- 150000003077 polyols Chemical class 0.000 claims description 25
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 16
- 229920000570 polyether Polymers 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- -1 N, N-dimethylaminopropyl Chemical group 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 claims description 4
- FZQMJOOSLXFQSU-UHFFFAOYSA-N 3-[3,5-bis[3-(dimethylamino)propyl]-1,3,5-triazinan-1-yl]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCN1CN(CCCN(C)C)CN(CCCN(C)C)C1 FZQMJOOSLXFQSU-UHFFFAOYSA-N 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- GUOCDOXXYQUWFS-UHFFFAOYSA-N 2-(2-aminoethyl)-3,4-dimethylphenol Chemical compound CC1=CC=C(O)C(CCN)=C1C GUOCDOXXYQUWFS-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- RIGCMCZFYMPTLC-UHFFFAOYSA-N n,n-dimethyl-3-(1,3,5-triazinan-1-yl)propan-1-amine Chemical compound CN(C)CCCN1CNCNC1 RIGCMCZFYMPTLC-UHFFFAOYSA-N 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920000582 polyisocyanurate Polymers 0.000 description 6
- 239000006260 foam Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000011495 polyisocyanurate Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- MMTOSBCMFDNOIY-UHFFFAOYSA-N 2-(chloromethyl)-3-methyloxirane Chemical compound CC1OC1CCl MMTOSBCMFDNOIY-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 241001026509 Kata Species 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000005829 trimerization reaction Methods 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- VUSYFNXNYLAECV-UHFFFAOYSA-N 2,3-bis(chloromethyl)oxirane Chemical compound ClCC1OC1CCl VUSYFNXNYLAECV-UHFFFAOYSA-N 0.000 description 1
- UKXROSORAUTSSH-UHFFFAOYSA-N 2-(1,2-dichloroethyl)oxirane Chemical compound ClCC(Cl)C1CO1 UKXROSORAUTSSH-UHFFFAOYSA-N 0.000 description 1
- MOBNLCPBAMKACS-UHFFFAOYSA-N 2-(1-chloroethyl)oxirane Chemical compound CC(Cl)C1CO1 MOBNLCPBAMKACS-UHFFFAOYSA-N 0.000 description 1
- DIYZRTRTCGAIKG-UHFFFAOYSA-N 2-(dichloromethyl)oxirane Chemical compound ClC(Cl)C1CO1 DIYZRTRTCGAIKG-UHFFFAOYSA-N 0.000 description 1
- VFEXYZINKMLLAK-UHFFFAOYSA-N 2-(trichloromethyl)oxirane Chemical compound ClC(Cl)(Cl)C1CO1 VFEXYZINKMLLAK-UHFFFAOYSA-N 0.000 description 1
- LHACVTZKOCVDBZ-UHFFFAOYSA-N 2-[3,5-bis[3-(dimethylamino)propyl]-1,3,5-triazinan-1-yl]ethanol Chemical compound CN(C)CCCN1CN(CCO)CN(CCCN(C)C)C1 LHACVTZKOCVDBZ-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000002105 tongue Anatomy 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1825—Catalysts containing secondary or tertiary amines or salts thereof having hydroxy or primary amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2669—Non-metals or compounds thereof
- C08G65/2672—Nitrogen or compounds thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S521/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S521/902—Cellular polymer containing an isocyanurate structure
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/021,517 US4228310A (en) | 1979-03-19 | 1979-03-19 | Polyol preparation |
| DE19803020341 DE3020341A1 (de) | 1979-03-19 | 1980-05-29 | Verfahren zur herstellung von polyaether-polyolen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/021,517 US4228310A (en) | 1979-03-19 | 1979-03-19 | Polyol preparation |
| DE19803020341 DE3020341A1 (de) | 1979-03-19 | 1980-05-29 | Verfahren zur herstellung von polyaether-polyolen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3020341A1 DE3020341A1 (de) | 1981-12-03 |
| DE3020341C2 true DE3020341C2 (en, 2012) | 1988-12-01 |
Family
ID=25785731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803020341 Granted DE3020341A1 (de) | 1979-03-19 | 1980-05-29 | Verfahren zur herstellung von polyaether-polyolen |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4228310A (en, 2012) |
| DE (1) | DE3020341A1 (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4521548A (en) * | 1983-04-12 | 1985-06-04 | The Dow Chemical Company | Preparation of polyether polyols |
| US4902723A (en) * | 1987-12-30 | 1990-02-20 | Union Carbide Chemicals And Plastics Company Inc. | Process for producing flexible polyurethane foam using hexahydro-s-triazine catalysts |
| US4883825A (en) * | 1987-12-30 | 1989-11-28 | Union Carbide Chemicals And Plastics Company Inc. | Process for the manufacture of low density, flexible polyurethane foams |
| US4814359A (en) * | 1987-12-30 | 1989-03-21 | Union Carbide Corporation | Process for producing flexible polyurethane foam using hexahydro-S-triazine catalysts |
| US5183923A (en) * | 1988-04-11 | 1993-02-02 | Texaco Chemical Company | Process for preparing primary hydroxyl-containing diols |
| US4888446A (en) * | 1988-04-11 | 1989-12-19 | Texaco Chemical Co. | Preparation of polyoxyalkylene glycol amines |
| JP2832276B2 (ja) * | 1989-06-30 | 1998-12-09 | テイ・エステック株式会社 | ウレタンフォーム成形品の製造方法 |
| US5395859A (en) * | 1991-06-21 | 1995-03-07 | Alliedsignal Inc. | Catalysts which stabilize hydrohalocarbon blowing agent in polyisocyanurate foam formulations during polymerization |
| DE59704012D1 (de) | 1997-04-16 | 2001-08-16 | Vantico Gmbh & Co Kg | Härtbare Mischungen aus Glycidylverbindungen, aminischen Härtern und heterocyclischen Beschleunigern |
| DE10156014A1 (de) * | 2001-11-15 | 2003-06-05 | Basf Ag | Verfahren zur Herstellung von Polyetheralkoholen |
| JP5655281B2 (ja) * | 2008-06-10 | 2015-01-21 | 東ソー株式会社 | 塩素化ポリエーテル及びそれよりなるポリウレタン |
| EP3299363A1 (en) * | 2016-09-23 | 2018-03-28 | Basf Se | 1, 3, 5 - triazinan compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3190927A (en) * | 1960-04-13 | 1965-06-22 | Wyandotte Chemicals Corp | Process for oxyalkylating solid polyols |
| GB1082673A (en) * | 1964-06-10 | 1967-09-06 | Pfizer Ltd | Polyethers |
| US3346557A (en) * | 1965-06-04 | 1967-10-10 | Wyandotte Chemicals Corp | Process for oxyalkylating solid polyols |
| US3745133A (en) * | 1968-02-05 | 1973-07-10 | Upjohn Co | Cellular isocyanurate containing polymers |
| US3988302A (en) * | 1974-05-24 | 1976-10-26 | Texaco Development Corporation | Polyurethanes prepared by reaction of organic polyisocyanate with brominated ester-containing polyols |
-
1979
- 1979-03-19 US US06/021,517 patent/US4228310A/en not_active Expired - Lifetime
-
1980
- 1980-05-29 DE DE19803020341 patent/DE3020341A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4228310A (en) | 1980-10-14 |
| DE3020341A1 (de) | 1981-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8127 | New person/name/address of the applicant |
Owner name: ARCO CHEMICAL CO., NEWTOWN SQUARE, PA., US |
|
| 8128 | New person/name/address of the agent |
Representative=s name: MUELLER, H., DIPL.-ING., 8000 MUENCHEN SCHUPFNER, |
|
| D2 | Grant after examination | ||
| 8380 | Miscellaneous part iii |
Free format text: SEITE 3, ZEILE 50 "11(GRAD)C" AENDERN IN "110(GRAD)C" |
|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |