GB1516019A - Process for the production of polysiloxane-polyoxyalkylene copolymers - Google Patents
Process for the production of polysiloxane-polyoxyalkylene copolymersInfo
- Publication number
- GB1516019A GB1516019A GB53017/76A GB5301776A GB1516019A GB 1516019 A GB1516019 A GB 1516019A GB 53017/76 A GB53017/76 A GB 53017/76A GB 5301776 A GB5301776 A GB 5301776A GB 1516019 A GB1516019 A GB 1516019A
- Authority
- GB
- United Kingdom
- Prior art keywords
- copolymer
- polysiloxane
- nco
- generally
- reacting
- 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
- 229920001577 copolymer Polymers 0.000 title abstract 9
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 239000003381 stabilizer Substances 0.000 abstract 7
- 239000005056 polyisocyanate Substances 0.000 abstract 6
- 229920001228 polyisocyanate Polymers 0.000 abstract 6
- 239000006260 foam Substances 0.000 abstract 5
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 4
- -1 Polysiloxane Polymers 0.000 abstract 4
- 229920000570 polyether Polymers 0.000 abstract 4
- 229920001296 polysiloxane Polymers 0.000 abstract 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 229920005830 Polyurethane Foam Polymers 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000011496 polyurethane foam Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 abstract 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 abstract 1
- OBETXYAYXDNJHR-UHFFFAOYSA-M 2-ethylhexanoate Chemical compound CCCCC(CC)C([O-])=O OBETXYAYXDNJHR-UHFFFAOYSA-M 0.000 abstract 1
- 239000004604 Blowing Agent Substances 0.000 abstract 1
- 229920002396 Polyurea Polymers 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000013256 coordination polymer Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000004205 dimethyl polysiloxane Substances 0.000 abstract 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 abstract 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000002524 organometallic group Chemical group 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 abstract 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 abstract 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 abstract 1
- 239000003021 water soluble solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0061—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof characterized by the use of several polymeric components
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2483/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
-
- 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
- Y10S521/905—Hydrophilic or hydrophobic cellular product
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Silicon Polymers (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752558523 DE2558523A1 (de) | 1975-12-24 | 1975-12-24 | Verfahren zur herstellung neuer polysiloxan-polyoxyalkylen-copolymerer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1516019A true GB1516019A (en) | 1978-06-28 |
Family
ID=5965529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB53017/76A Expired GB1516019A (en) | 1975-12-24 | 1976-12-20 | Process for the production of polysiloxane-polyoxyalkylene copolymers |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4096162A (https=) |
| JP (1) | JPS5281400A (https=) |
| AT (1) | AT356893B (https=) |
| AU (1) | AU2092776A (https=) |
| BE (1) | BE849790A (https=) |
| BR (1) | BR7608665A (https=) |
| CA (1) | CA1069242A (https=) |
| DE (1) | DE2558523A1 (https=) |
| ES (1) | ES454529A1 (https=) |
| FR (1) | FR2336435A1 (https=) |
| GB (1) | GB1516019A (https=) |
| IT (1) | IT1066681B (https=) |
| NL (1) | NL7614355A (https=) |
| SE (1) | SE7614440L (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111393657A (zh) * | 2019-09-04 | 2020-07-10 | 杭州师范大学 | 一种有机硅改性聚氨酯的制备方法 |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4350777A (en) * | 1980-03-28 | 1982-09-21 | Bayer Aktiengesellschaft | Impermeable molded articles of cellular polyurethane elastomers produced with organofunctional polysiloxane-derivatives and their use as spring elements |
| DE3149619A1 (de) * | 1981-12-15 | 1983-07-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von, als trennmittel fuer forminnenlacke geeigneten, polyisocyanat-additionsprodukten, sowie ihre verwendung als formtrennmittel fuer forminnenlacke bei der herstellung von mit einer lackschicht versehenen formkunststoffen |
| DE3812481A1 (de) * | 1987-08-26 | 1989-03-09 | Bayer Ag | Wasserhaertende polymerzubereitung |
| US5574122A (en) * | 1995-09-29 | 1996-11-12 | Bayer Corporation | Low surface energy polyisocyanates and their use in one- or two-component coating compositions |
| ES2131000B1 (es) * | 1997-06-05 | 2000-03-01 | Betere Fab Lucia Antonio | Derivados de poliuretano que contienen cadenas polimericas de base silicio. |
| DE19807022A1 (de) * | 1998-02-19 | 1999-08-26 | Wacker Chemie Gmbh | Kohlenstoffreste aufweisende Organosiliciumverbindungen |
| DE102007046187A1 (de) | 2007-09-26 | 2009-04-09 | Bayer Materialscience Ag | Dachmodul |
| DE102008051882A1 (de) | 2008-10-16 | 2010-04-29 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyetheresterpolyolen |
| DE102009005712A1 (de) | 2009-01-22 | 2010-07-29 | Bayer Materialscience Ag | Polyurethanvergussmassen |
| DE102009005711A1 (de) | 2009-01-22 | 2010-07-29 | Bayer Materialscience Ag | Polyurethanvergussmassen |
| US20110230581A1 (en) | 2010-03-17 | 2011-09-22 | Bayer Materialscience Llc | Process for the production of polyether polyols with a high ethylene oxide content |
| DE102010031684A1 (de) | 2010-07-20 | 2012-01-26 | Bayer Materialscience Ag | Polyurethane mit hoher Lichtbrechung |
| DE102010031683A1 (de) | 2010-07-20 | 2012-01-26 | Bayer Materialscience Ag | Polyisocyanatgemische |
| DE102010031681A1 (de) | 2010-07-20 | 2012-01-26 | Bayer Materialscience Ag | Polyurethane mit geringem Volumenschrumpf |
| ITMI20101380A1 (it) | 2010-07-27 | 2012-01-28 | Dow Global Technologies Inc | Pannello composito poliuretanico a basso impatto ambientale |
| DE102010063237A1 (de) * | 2010-12-16 | 2012-06-21 | Evonik Goldschmidt Gmbh | Siliconstabilisatoren für Polyurethan- oder Polyisocyanurat-Hartschaumstoffe |
| KR20140007822A (ko) | 2010-12-20 | 2014-01-20 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 폴리에테르 에스테르 폴리올의 제조 방법 |
| DE102013211349A1 (de) | 2013-06-18 | 2014-12-18 | Evonik Industries Ag | Isocyanat-Siloxanpolyether-Zusammensetzung |
| EP3330308A1 (de) | 2016-12-05 | 2018-06-06 | Covestro Deutschland AG | Verfahren zur herstellung von tdi-basierten polyurethanweichschaumstoffen enthaltend organische säureanhydride und/oder organische säurechloride |
| US11124615B2 (en) | 2019-03-29 | 2021-09-21 | Covestro Llc | Laminated parts containing a slip resistant and water resistant outer layer and methods for their production |
| EP3741788A1 (de) | 2019-05-24 | 2020-11-25 | Covestro Deutschland AG | Verfahren zur herstellung von polyoxyalkylenpolyol-mischungen |
| EP3760659A1 (de) | 2019-07-01 | 2021-01-06 | Covestro Deutschland AG | Amingestartete polyole als einbaubare katalysatoren im hr-schaum |
| EP3838963A1 (de) | 2019-12-17 | 2021-06-23 | Covestro Deutschland AG | Verfahren zur herstellung von polyoxyalkylenpolyesterpolyolen |
| WO2022096390A1 (de) | 2020-11-06 | 2022-05-12 | Covestro Deutschland Ag | Verfahren zur herstellung eines polyol-gemisches |
| CN120418084A (zh) | 2023-01-17 | 2025-08-01 | 科思创有限公司 | 含有硬质聚氨酯外层的层压部件及其制备方法 |
| CN116836363A (zh) * | 2023-05-19 | 2023-10-03 | 西北工业大学 | 一种宽温适应性htpb型聚氨酯弹性体体系及制备、使用方法 |
| EP4731701A1 (de) | 2023-06-23 | 2026-04-29 | Covestro Deutschland AG | Verfahren zur herstellung eines polyoxyalkylenpolyols |
| EP4480993A1 (de) | 2023-06-23 | 2024-12-25 | Covestro Deutschland AG | Verfahren zur herstellung eines polyoxyalkylenpolyols |
| WO2025131996A1 (de) | 2023-12-21 | 2025-06-26 | Covestro Deutschland Ag | Verbindung enthaltend oximische hydroxylgruppen und deren herstellungsverfahren |
| EP4574869A1 (de) | 2023-12-21 | 2025-06-25 | Covestro Deutschland AG | Verbindung enthaltend oximische hydroxylgruppen und deren herstellungsverfahren |
| EP4644451A1 (de) | 2024-04-29 | 2025-11-05 | Covestro Deutschland AG | Verbindung enthaltend aromatische hydroxylgruppen und deren herstellungsverfahren |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA695633A (en) * | 1961-07-31 | 1964-10-06 | A. Haluska Loren | Siloxane glycol branch copolymers |
| US3246048A (en) * | 1962-09-14 | 1966-04-12 | Dow Corning | Organosiloxane-polyether urethanes |
| US3505377A (en) * | 1966-08-12 | 1970-04-07 | Union Carbide Corp | Siloxane-oxyalkylene copolymer foam stabilizers |
| DE1929034B2 (de) * | 1969-06-07 | 1972-04-20 | Farbenfabriken Bayer Ag, 5090 Lever Kusen | Verfahren zur herstellung von flammfesten urethangruppen aufweisenden schaumstoffen |
| DE2002064C2 (de) * | 1970-01-17 | 1983-09-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von flammwidrigen elastischen oder halbelastischen Schaumstoffen |
| GB1339441A (en) * | 1970-06-19 | 1973-12-05 | Dunlop Holdings Ltd | Polyurethane foams |
| US3896123A (en) * | 1972-04-06 | 1975-07-22 | Gen Electric | Silyl cyanurates |
-
1975
- 1975-12-24 DE DE19752558523 patent/DE2558523A1/de not_active Withdrawn
-
1976
- 1976-12-02 CA CA267,042A patent/CA1069242A/en not_active Expired
- 1976-12-06 US US05/748,029 patent/US4096162A/en not_active Expired - Lifetime
- 1976-12-20 GB GB53017/76A patent/GB1516019A/en not_active Expired
- 1976-12-22 SE SE7614440A patent/SE7614440L/xx not_active Application Discontinuation
- 1976-12-22 AT AT953176A patent/AT356893B/de not_active IP Right Cessation
- 1976-12-22 IT IT52739/76A patent/IT1066681B/it active
- 1976-12-23 BR BR7608665A patent/BR7608665A/pt unknown
- 1976-12-23 NL NL7614355A patent/NL7614355A/xx not_active Application Discontinuation
- 1976-12-23 BE BE173577A patent/BE849790A/xx not_active IP Right Cessation
- 1976-12-23 ES ES454529A patent/ES454529A1/es not_active Expired
- 1976-12-24 AU AU20927/76A patent/AU2092776A/en not_active Expired
- 1976-12-24 FR FR7639096A patent/FR2336435A1/fr active Granted
- 1976-12-24 JP JP15516576A patent/JPS5281400A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111393657A (zh) * | 2019-09-04 | 2020-07-10 | 杭州师范大学 | 一种有机硅改性聚氨酯的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2336435B1 (https=) | 1980-06-06 |
| NL7614355A (nl) | 1977-06-28 |
| IT1066681B (it) | 1985-03-12 |
| CA1069242A (en) | 1980-01-01 |
| JPS5281400A (en) | 1977-07-07 |
| SE7614440L (sv) | 1977-06-25 |
| AU2092776A (en) | 1978-06-29 |
| BE849790A (fr) | 1977-06-23 |
| AT356893B (de) | 1980-05-27 |
| BR7608665A (pt) | 1978-01-03 |
| ES454529A1 (es) | 1977-12-01 |
| US4096162A (en) | 1978-06-20 |
| ATA953176A (de) | 1979-10-15 |
| DE2558523A1 (de) | 1977-07-07 |
| FR2336435A1 (fr) | 1977-07-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |