CN106220667B - 螺环有机硅化合物及其应用 - Google Patents
螺环有机硅化合物及其应用 Download PDFInfo
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- CN106220667B CN106220667B CN201610581760.5A CN201610581760A CN106220667B CN 106220667 B CN106220667 B CN 106220667B CN 201610581760 A CN201610581760 A CN 201610581760A CN 106220667 B CN106220667 B CN 106220667B
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- 150000003961 organosilicon compounds Chemical class 0.000 title claims abstract description 47
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 28
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 26
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 150000002367 halogens Chemical class 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 239000012188 paraffin wax Substances 0.000 claims abstract description 13
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 39
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- -1 Methyl Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 150000003384 small molecules Chemical class 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 claims description 12
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 claims description 12
- 229910000077 silane Inorganic materials 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000011244 liquid electrolyte Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 150000003950 cyclic amides Chemical class 0.000 claims description 3
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 3
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 150000003377 silicon compounds Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 23
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 abstract description 13
- 239000002994 raw material Substances 0.000 abstract description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 7
- 229920001971 elastomer Polymers 0.000 abstract description 7
- 239000000806 elastomer Substances 0.000 abstract description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003292 glue Substances 0.000 description 13
- 238000010586 diagram Methods 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 6
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012916 structural analysis Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- MHLPUDQXLUBKRS-UHFFFAOYSA-N 5-methyl-5-propyl-1,3-dioxane Chemical class CCCC1(C)COCOC1 MHLPUDQXLUBKRS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007784 solid electrolyte Substances 0.000 description 2
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- DIJRHOZMLZRNLM-UHFFFAOYSA-N dimethoxy-methyl-(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](C)(OC)CCC(F)(F)F DIJRHOZMLZRNLM-UHFFFAOYSA-N 0.000 description 1
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the 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
- 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
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
-
- 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
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl 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
- 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
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing 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
- 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
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
Description
Claims (16)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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CN201610581760.5A CN106220667B (zh) | 2016-07-21 | 2016-07-21 | 螺环有机硅化合物及其应用 |
PCT/CN2017/093264 WO2018014819A1 (zh) | 2016-07-21 | 2017-07-18 | 螺环有机硅化合物及其应用 |
Applications Claiming Priority (1)
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CN201610581760.5A CN106220667B (zh) | 2016-07-21 | 2016-07-21 | 螺环有机硅化合物及其应用 |
Publications (2)
Publication Number | Publication Date |
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CN106220667A CN106220667A (zh) | 2016-12-14 |
CN106220667B true CN106220667B (zh) | 2018-10-30 |
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CN201610581760.5A Active CN106220667B (zh) | 2016-07-21 | 2016-07-21 | 螺环有机硅化合物及其应用 |
Country Status (2)
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CN (1) | CN106220667B (zh) |
WO (1) | WO2018014819A1 (zh) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106220667B (zh) * | 2016-07-21 | 2018-10-30 | 北京航空航天大学 | 螺环有机硅化合物及其应用 |
CN107759791B (zh) * | 2017-05-05 | 2021-07-06 | 北京航空航天大学 | 含有硅氧八元环的有机硅聚合物、交联体与制备方法 |
CN107698617B (zh) * | 2017-09-04 | 2020-07-28 | 北京航空航天大学 | 含有硅氧八元环的有机硅聚合物、其合成及应用 |
JP7023511B2 (ja) * | 2018-06-28 | 2022-02-22 | 国立研究開発法人産業技術総合研究所 | 環状シロキサン化合物の製造方法、及び環状シロキサン化合物 |
CR20220316A (es) | 2019-12-06 | 2022-10-07 | Vertex Pharma | Tetrahidrofuranos sustituidos como moduladores de canales de sodio |
AR126073A1 (es) | 2021-06-04 | 2023-09-06 | Vertex Pharma | N-(hidroxialquil(hetero)aril)tetrahidrofuran carboxamidas como moduladores de canales de sodio |
CN116120833A (zh) * | 2021-11-12 | 2023-05-16 | 北京深云智合科技有限公司 | 含有硅氧八元环的有机硅聚合物在阻燃材料中的应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5376595A (en) * | 1992-08-28 | 1994-12-27 | Allied-Signal Inc. | Silicon carboxide ceramics from spirosiloxanes |
CN103492464A (zh) * | 2011-04-20 | 2014-01-01 | 中央硝子株式会社 | 硅氧烷化合物及其固化物 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US9751899B2 (en) * | 2015-04-15 | 2017-09-05 | Richard M. Laine | Synthesis method of alkoxysilanes |
CN106220667B (zh) * | 2016-07-21 | 2018-10-30 | 北京航空航天大学 | 螺环有机硅化合物及其应用 |
-
2016
- 2016-07-21 CN CN201610581760.5A patent/CN106220667B/zh active Active
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2017
- 2017-07-18 WO PCT/CN2017/093264 patent/WO2018014819A1/zh active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5376595A (en) * | 1992-08-28 | 1994-12-27 | Allied-Signal Inc. | Silicon carboxide ceramics from spirosiloxanes |
CN103492464A (zh) * | 2011-04-20 | 2014-01-01 | 中央硝子株式会社 | 硅氧烷化合物及其固化物 |
Non-Patent Citations (1)
Title |
---|
Flash vacuum pyrolysis (FVP) of 2,7-dimethyl-2,3:7,8-diepoxy-5-silaspiro[4.4]nonane with cyclotrisiloxanes. Synthesis ofspirocyclosiloxanes. Characterization of silica formed by FVP of 2,7-dimethyl-2,3:7,8-diepoxy-5-silaspiro[4.4]nonane;George K. Henry et al.;《Organometallics》;19861231;第1818-1823页 * |
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WO2018014819A1 (zh) | 2018-01-25 |
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Inventor after: Liu Yuzhou Inventor after: Yu Jianyi Inventor after: Han Ye Inventor before: Liu Yuzhou Inventor before: Yu Jianyi Inventor before: Han Ye |
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Effective date of registration: 20230427 Address after: No. 1008-1260, 1st Floor, Building A, Building 1, Yard 2, Yongcheng North Road, Haidian District, Beijing, 100000 Patentee after: Beijing Shenyun Zhihe Technology Co.,Ltd. Address before: 100094 No. 15, floor 1, block B, building 1, yard 2, Yongcheng North Road, Haidian District, Beijing Patentee before: Beijing Siyan New Material Technology Co.,Ltd. |