CN1911886A - Production technology of bi-tribydroxy methyl propane and/or trihydroxy methyl propane methylal - Google Patents
Production technology of bi-tribydroxy methyl propane and/or trihydroxy methyl propane methylal Download PDFInfo
- Publication number
- CN1911886A CN1911886A CN 200610086255 CN200610086255A CN1911886A CN 1911886 A CN1911886 A CN 1911886A CN 200610086255 CN200610086255 CN 200610086255 CN 200610086255 A CN200610086255 A CN 200610086255A CN 1911886 A CN1911886 A CN 1911886A
- Authority
- CN
- China
- Prior art keywords
- tmp
- trimethylolpropane
- methylal
- ditrimethylolpropane
- reaction
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- 238000005516 engineering process Methods 0.000 title description 3
- GQPBUEXGBKVDDE-UHFFFAOYSA-N COCOC.OC(CCC)(O)O Chemical compound COCOC.OC(CCC)(O)O GQPBUEXGBKVDDE-UHFFFAOYSA-N 0.000 title 1
- 235000013847 iso-butane Nutrition 0.000 title 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 title 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 title 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims abstract description 98
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims abstract description 90
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000007788 liquid Substances 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 23
- 238000007323 disproportionation reaction Methods 0.000 claims abstract description 9
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000006266 etherification reaction Methods 0.000 claims abstract description 3
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims description 64
- 238000000605 extraction Methods 0.000 claims description 53
- 239000002904 solvent Substances 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 230000018044 dehydration Effects 0.000 claims description 18
- 238000006297 dehydration reaction Methods 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000012074 organic phase Substances 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 8
- 230000008020 evaporation Effects 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 241000282326 Felis catus Species 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 238000007701 flash-distillation Methods 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 5
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 5
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 239000003637 basic solution Substances 0.000 claims description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000012856 packing Methods 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 229940043232 butyl acetate Drugs 0.000 claims description 2
- 238000010612 desalination reaction Methods 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 abstract description 4
- UFZHRTLJOSFQNY-UHFFFAOYSA-N dimethoxymethane 2-ethyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound COCOC.C(O)C(CC)(CO)CO UFZHRTLJOSFQNY-UHFFFAOYSA-N 0.000 abstract 2
- 238000005829 trimerization reaction Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 9
- 150000001241 acetals Chemical class 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 4
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB200610086255XA CN100400489C (en) | 2006-08-24 | 2006-08-24 | Production technology of bi-tribydroxy methyl propane and/or trihydroxy methyl propane methylal |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB200610086255XA CN100400489C (en) | 2006-08-24 | 2006-08-24 | Production technology of bi-tribydroxy methyl propane and/or trihydroxy methyl propane methylal |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1911886A true CN1911886A (en) | 2007-02-14 |
CN100400489C CN100400489C (en) | 2008-07-09 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB200610086255XA Expired - Fee Related CN100400489C (en) | 2006-08-24 | 2006-08-24 | Production technology of bi-tribydroxy methyl propane and/or trihydroxy methyl propane methylal |
Country Status (1)
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CN (1) | CN100400489C (en) |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101092410B (en) * | 2007-05-21 | 2010-04-14 | 吉化集团公司 | Method and equipment for preparing cyclic trimethylolpropane formal by using heavy residue of trimethylolpropane |
CN101821222A (en) * | 2007-10-30 | 2010-09-01 | 三菱瓦斯化学株式会社 | Process for production of ditrimethylolpropane |
CN102807477A (en) * | 2012-09-12 | 2012-12-05 | 上海北凯实业有限公司 | Method for synthesizing dipentaerythritol from mono-pentaerythritol |
CN101550070B (en) * | 2008-12-30 | 2013-07-17 | 湖北三江化工有限责任公司 | Production process of ditrimethylolpropane |
CN102143931B (en) * | 2008-08-16 | 2014-06-18 | 朗盛德国有限责任公司 | Method for isolating di-trimethylol propane |
CN104024200A (en) * | 2011-11-19 | 2014-09-03 | Oxea有限责任公司 | Method for Recovering Di-Trimethylolpropane By Distillation |
CN104496960A (en) * | 2014-11-24 | 2015-04-08 | 张家港保税区冠祥贸易有限公司 | Di(trimethylolpropane)-based biodegradable cycloacetal alkene monomer, and preparation method thereof |
TWI561505B (en) * | 2010-09-07 | 2016-12-11 | Mitsubishi Gas Chemical Co | Method of producing di(trimethylolpropane) |
CN108383826A (en) * | 2018-03-09 | 2018-08-10 | 天津博奥新材料科技有限公司 | A kind of preparation method of cyclic trimethylolpropane formal |
CN109369333A (en) * | 2018-11-27 | 2019-02-22 | 濮阳市永安化工有限公司 | The method of trimethylolpropane is isolated from trimethylolpropane light component |
CN110372475A (en) * | 2019-08-16 | 2019-10-25 | 南通百川新材料有限公司 | Synthesis process of trimethylolpropane with low acidity and high yield |
CN110577462A (en) * | 2019-10-09 | 2019-12-17 | 江苏汉凯工程技术有限公司 | method and device for recovering ditrimethylolpropane |
CN114181044A (en) * | 2021-12-03 | 2022-03-15 | 宁夏百川科技有限公司 | Preparation method of high-purity ditrimethylolpropane |
CN115925540A (en) * | 2022-11-09 | 2023-04-07 | 广东聚石科技研究有限公司 | Trimethylolpropane medium-carbon chain ester and preparation method and application thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4076721A (en) * | 1975-06-11 | 1978-02-28 | Ihara Chemical Industry Co., Ltd. | Process for producing saccharin |
EP1491521A1 (en) * | 2003-06-13 | 2004-12-29 | Mitsubishi Gas Chemical Company, Inc. | Method for producing ditrimethylolpropane |
-
2006
- 2006-08-24 CN CNB200610086255XA patent/CN100400489C/en not_active Expired - Fee Related
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101092410B (en) * | 2007-05-21 | 2010-04-14 | 吉化集团公司 | Method and equipment for preparing cyclic trimethylolpropane formal by using heavy residue of trimethylolpropane |
CN101821222A (en) * | 2007-10-30 | 2010-09-01 | 三菱瓦斯化学株式会社 | Process for production of ditrimethylolpropane |
CN101821222B (en) * | 2007-10-30 | 2013-08-21 | 三菱瓦斯化学株式会社 | Process for production of ditrimethylolpropane |
CN102143931B (en) * | 2008-08-16 | 2014-06-18 | 朗盛德国有限责任公司 | Method for isolating di-trimethylol propane |
CN101550070B (en) * | 2008-12-30 | 2013-07-17 | 湖北三江化工有限责任公司 | Production process of ditrimethylolpropane |
TWI561505B (en) * | 2010-09-07 | 2016-12-11 | Mitsubishi Gas Chemical Co | Method of producing di(trimethylolpropane) |
CN104024200B (en) * | 2011-11-19 | 2016-08-31 | Oxea有限责任公司 | The method being recovered by distillation double-trimethylolpropane |
CN104024200A (en) * | 2011-11-19 | 2014-09-03 | Oxea有限责任公司 | Method for Recovering Di-Trimethylolpropane By Distillation |
CN102807477A (en) * | 2012-09-12 | 2012-12-05 | 上海北凯实业有限公司 | Method for synthesizing dipentaerythritol from mono-pentaerythritol |
CN104496960A (en) * | 2014-11-24 | 2015-04-08 | 张家港保税区冠祥贸易有限公司 | Di(trimethylolpropane)-based biodegradable cycloacetal alkene monomer, and preparation method thereof |
CN108383826A (en) * | 2018-03-09 | 2018-08-10 | 天津博奥新材料科技有限公司 | A kind of preparation method of cyclic trimethylolpropane formal |
CN109369333A (en) * | 2018-11-27 | 2019-02-22 | 濮阳市永安化工有限公司 | The method of trimethylolpropane is isolated from trimethylolpropane light component |
CN110372475A (en) * | 2019-08-16 | 2019-10-25 | 南通百川新材料有限公司 | Synthesis process of trimethylolpropane with low acidity and high yield |
CN110577462A (en) * | 2019-10-09 | 2019-12-17 | 江苏汉凯工程技术有限公司 | method and device for recovering ditrimethylolpropane |
CN114181044A (en) * | 2021-12-03 | 2022-03-15 | 宁夏百川科技有限公司 | Preparation method of high-purity ditrimethylolpropane |
CN114181044B (en) * | 2021-12-03 | 2024-05-17 | 宁夏百川科技有限公司 | Preparation method of high-purity ditrimethylolpropane |
CN115925540A (en) * | 2022-11-09 | 2023-04-07 | 广东聚石科技研究有限公司 | Trimethylolpropane medium-carbon chain ester and preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
CN100400489C (en) | 2008-07-09 |
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Owner name: JIANGSU BOLI'AO CHEMICAL CO.,LTD. Free format text: FORMER OWNER: WANG QIANG Effective date: 20081107 |
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Effective date of registration: 20081107 Address after: Jiangsu province Liyang City Nandu town Qiang Bu strong industrial park Patentee after: Jiangsu bourriau Chemical Co. Ltd. Address before: Jiangsu province Liyang City Nandu town Qiang Bu strong industrial park Patentee before: Wang Qiang |
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Owner name: LANXESS (LIYANG) POLYOL CO., LTD. Free format text: FORMER OWNER: JIANGSU BOLI'AO CHEMICAL CO.,LTD. Effective date: 20090918 |
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Effective date of registration: 20090918 Address after: Jiangsu province Liyang City Nandu town Qiang Bu strong Road No. 36 Patentee after: LANXESS (Liyang) Co., Ltd. polyol Address before: Jiangsu province Liyang City Nandu town Qiang Bu strong industrial park Patentee before: Jiangsu bourriau Chemical Co. Ltd. |
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Granted publication date: 20080709 Termination date: 20190824 |
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