CN1814647A - Method for preparing high-molecular-weight polycarbonate - Google Patents
Method for preparing high-molecular-weight polycarbonate Download PDFInfo
- Publication number
- CN1814647A CN1814647A CN 200610049707 CN200610049707A CN1814647A CN 1814647 A CN1814647 A CN 1814647A CN 200610049707 CN200610049707 CN 200610049707 CN 200610049707 A CN200610049707 A CN 200610049707A CN 1814647 A CN1814647 A CN 1814647A
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- China
- Prior art keywords
- described preparation
- molecular weight
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- epoxy compounds
- bmim
- 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.)
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- 229920000515 polycarbonate Polymers 0.000 title claims description 13
- 239000004417 polycarbonate Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 239000002262 Schiff base Substances 0.000 claims abstract description 12
- 239000002184 metal Substances 0.000 claims abstract description 11
- 229910052751 metal Inorganic materials 0.000 claims abstract description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 25
- -1 compound ion Chemical class 0.000 claims description 22
- 235000011089 carbon dioxide Nutrition 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000004593 Epoxy Chemical class 0.000 claims description 16
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000002608 ionic liquid Substances 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 7
- 150000002500 ions Chemical class 0.000 claims description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000013110 organic ligand Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 claims description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 2
- 229910021381 transition metal chloride Inorganic materials 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 1
- 238000009826 distribution Methods 0.000 abstract description 12
- 229920001577 copolymer Polymers 0.000 abstract description 7
- 238000007334 copolymerization reaction Methods 0.000 abstract description 6
- 239000002131 composite material Substances 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- 150000004753 Schiff bases Chemical class 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 238000013329 compounding Methods 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 description 9
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VZHHNBNSMNNUAD-UHFFFAOYSA-N cobalt 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound [Co].OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VZHHNBNSMNNUAD-UHFFFAOYSA-N 0.000 description 6
- 150000002924 oxiranes Chemical group 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 229910000071 diazene Inorganic materials 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000466 oxiranyl group Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 239000012967 coordination catalyst Substances 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 229920006238 degradable plastic Polymers 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
The experiment sequence number | Epoxy compounds | Schiff base metal complex | Ionic liquid | Temperature | Pressure | Time | Molecular weight | Alternating structure | Molecular weight distribution |
3 4 5 6 7 8 9 10 11 12 | Ethylene oxide propylene oxide epoxychloropropane epoxy styrene epoxypinane epoxide ring hexene epoxide ring hexene epoxide ring hexene epoxide ring hexene epoxide ring hexene | Salen Co Salen Co Salen Co Salen Co Salen Co Salen Al Salen Mn Salen Fe Salen Ni Salen Co | [Et 4N][BF 4] [Me 4N][BF 4] [Et 4N][PF 6] [Et 4N][PF 6] [Et 4N][BF 4] [Et 4N][BF 4] [Bmim][PF 6] [Emim][NO 3] [Bmim][PF 6] [Emim][BF 4] | 30 30 30 30 30 30 20 60 80 30 | 0.5 2.0 2.0 0.1 1.0 2.0 2.0 5.0 2.0 2.0 | 20 10 10 20 10 5 10 5 2 5 | 30500 33600 23500 28900 25400 33900 12000 21500 23600 36800 | 98 99 98 98 99 99 98 96 98 99 | 1.25 1.12 1.28 1.21 1.18 1.08 1.45 1.32 1.36 1.16 |
Claims (10)
Priority Applications (1)
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CNB2006100497077A CN100355804C (en) | 2006-03-06 | 2006-03-06 | Method for preparing high-molecular-weight polycarbonate |
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CNB2006100497077A CN100355804C (en) | 2006-03-06 | 2006-03-06 | Method for preparing high-molecular-weight polycarbonate |
Publications (2)
Publication Number | Publication Date |
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CN1814647A true CN1814647A (en) | 2006-08-09 |
CN100355804C CN100355804C (en) | 2007-12-19 |
Family
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Family Applications (1)
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CNB2006100497077A Expired - Fee Related CN100355804C (en) | 2006-03-06 | 2006-03-06 | Method for preparing high-molecular-weight polycarbonate |
Country Status (1)
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100463932C (en) * | 2007-02-12 | 2009-02-25 | 江苏中科金龙化工股份有限公司 | Production method of aliphatic polycarbonate resin |
CN101302332B (en) * | 2007-05-10 | 2011-08-03 | 东丽纤维研究所(中国)有限公司 | Carbon dioxide-cyclohexene oxide copolymer brittlement modified method |
CN103191779A (en) * | 2013-04-11 | 2013-07-10 | 南京大学 | Chiral schiff alkali metal catalyst supported by ionic liquid and preparation method and use thereof |
CN103333329A (en) * | 2013-06-27 | 2013-10-02 | 昆明理工大学 | Method for preparing polycarbonate by copolymerizing carbon dioxide and alpha-pinene derivatives |
CN106377976A (en) * | 2016-10-13 | 2017-02-08 | 浙江大学 | Method for realizing high-efficiency NO trapping by utilizing polyomidazolyl boric acid ionic liquid |
CN109054011A (en) * | 2018-07-16 | 2018-12-21 | 中国科学院长春应用化学研究所 | A kind of preparation method of schiff bases cobalt compound, preparation method and polycarbonate |
CN116410455A (en) * | 2023-03-03 | 2023-07-11 | 天津工业大学 | Method for preparing polyester by copolymerization of carbon dioxide and epoxide |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI586641B (en) * | 2016-04-13 | 2017-06-11 | 國立中興大學 | Bimetallic lanthanide complex, fabricating method and use thereof, polycarbonate and method of manufacturing polycarbonate |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6870004B1 (en) * | 2001-08-24 | 2005-03-22 | Northwestern University | Metal-ligand complexes and related methods of chemical CO2 fixation |
CN100334130C (en) * | 2004-02-27 | 2007-08-29 | 大连理工大学 | Preparation process of polyester carbonate with high molecular weight whole alternant structure |
CN1663978A (en) * | 2005-03-21 | 2005-09-07 | 大连理工大学 | Process for preparing polycarbonate with optical activity |
-
2006
- 2006-03-06 CN CNB2006100497077A patent/CN100355804C/en not_active Expired - Fee Related
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100463932C (en) * | 2007-02-12 | 2009-02-25 | 江苏中科金龙化工股份有限公司 | Production method of aliphatic polycarbonate resin |
CN101302332B (en) * | 2007-05-10 | 2011-08-03 | 东丽纤维研究所(中国)有限公司 | Carbon dioxide-cyclohexene oxide copolymer brittlement modified method |
CN103191779A (en) * | 2013-04-11 | 2013-07-10 | 南京大学 | Chiral schiff alkali metal catalyst supported by ionic liquid and preparation method and use thereof |
CN103333329A (en) * | 2013-06-27 | 2013-10-02 | 昆明理工大学 | Method for preparing polycarbonate by copolymerizing carbon dioxide and alpha-pinene derivatives |
CN106377976A (en) * | 2016-10-13 | 2017-02-08 | 浙江大学 | Method for realizing high-efficiency NO trapping by utilizing polyomidazolyl boric acid ionic liquid |
CN106377976B (en) * | 2016-10-13 | 2018-11-30 | 浙江大学 | A method of realizing that NO is efficiently trapped using polyazole ylboronic acid ionic liquid |
CN109054011A (en) * | 2018-07-16 | 2018-12-21 | 中国科学院长春应用化学研究所 | A kind of preparation method of schiff bases cobalt compound, preparation method and polycarbonate |
CN116410455A (en) * | 2023-03-03 | 2023-07-11 | 天津工业大学 | Method for preparing polyester by copolymerization of carbon dioxide and epoxide |
CN116410455B (en) * | 2023-03-03 | 2023-11-14 | 天津工业大学 | Method for preparing polyester by copolymerization of carbon dioxide and epoxide |
Also Published As
Publication number | Publication date |
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CN100355804C (en) | 2007-12-19 |
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Assignee: Ningbo Xinke Textile Auxiliary Co., LTd. Assignor: Zhejiang University Contract fulfillment period: 2008.2.10 to 2013.1.31 contract change Contract record no.: 2009330000575 Denomination of invention: Method for preparing high-molecular-weight polycarbonate Granted publication date: 20071219 License type: Exclusive license Record date: 2009.4.8 |
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Free format text: EXCLUSIVE LICENSE; TIME LIMIT OF IMPLEMENTING CONTACT: 2008.2.10 TO 2013.1.31; CHANGE OF CONTRACT Name of requester: NINGBO XINKE TEXTILE AIDS CO., LTD. Effective date: 20090408 |
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Granted publication date: 20071219 Termination date: 20120306 |