KR100979461B1 - 시클로알케닐실란폴리올 유도체와 이의 제조방법 - Google Patents
시클로알케닐실란폴리올 유도체와 이의 제조방법 Download PDFInfo
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- KR100979461B1 KR100979461B1 KR1020070106843A KR20070106843A KR100979461B1 KR 100979461 B1 KR100979461 B1 KR 100979461B1 KR 1020070106843 A KR1020070106843 A KR 1020070106843A KR 20070106843 A KR20070106843 A KR 20070106843A KR 100979461 B1 KR100979461 B1 KR 100979461B1
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- South Korea
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- formula
- cyclopentenyl
- enyl
- nmr
- octa
- Prior art date
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- 238000002360 preparation method Methods 0.000 title abstract description 3
- -1 silane compound Chemical class 0.000 claims abstract description 47
- 229920005862 polyol Polymers 0.000 claims abstract description 14
- 229910000077 silane Inorganic materials 0.000 claims abstract description 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 13
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 229910052809 inorganic oxide Inorganic materials 0.000 claims 1
- 239000012756 surface treatment agent Substances 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 abstract description 9
- 230000004048 modification Effects 0.000 abstract description 7
- 238000012986 modification Methods 0.000 abstract description 7
- 229920005573 silicon-containing polymer Polymers 0.000 abstract description 7
- 239000010409 thin film Substances 0.000 abstract description 7
- 229910010272 inorganic material Inorganic materials 0.000 abstract description 6
- 239000011147 inorganic material Substances 0.000 abstract description 6
- 230000007062 hydrolysis Effects 0.000 abstract description 5
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 5
- 150000004756 silanes Chemical class 0.000 abstract description 5
- 239000003377 acid catalyst Substances 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 125000005372 silanol group Chemical group 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- IXXKXGNJIZVGRW-UHFFFAOYSA-N cyclopent-2-en-1-yl(trimethoxy)silane Chemical class CO[Si](OC)(OC)C1CCC=C1 IXXKXGNJIZVGRW-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VMXOYPPCIRAACF-UHFFFAOYSA-N C1(C=CCC1)[Si](OC)(OC)C Chemical compound C1(C=CCC1)[Si](OC)(OC)C VMXOYPPCIRAACF-UHFFFAOYSA-N 0.000 description 3
- CUIBTMQTFODVGT-UHFFFAOYSA-N C12C(CC(C=C1)CC2)[Si](OC)(OC)C Chemical compound C12C(CC(C=C1)CC2)[Si](OC)(OC)C CUIBTMQTFODVGT-UHFFFAOYSA-N 0.000 description 3
- OEHOXKDFHJVEFG-UHFFFAOYSA-N C12C(CC(C=C1)CC2)[Si](OC)(OC)OC Chemical compound C12C(CC(C=C1)CC2)[Si](OC)(OC)OC OEHOXKDFHJVEFG-UHFFFAOYSA-N 0.000 description 3
- QCLAYDZECRPODO-UHFFFAOYSA-N CC1=C(CC(CC1)[Si](OC)(OC)OC)C Chemical compound CC1=C(CC(CC1)[Si](OC)(OC)OC)C QCLAYDZECRPODO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- JSAXPYDTIXIPSX-UHFFFAOYSA-N cyclohex-3-en-1-yl(trimethoxy)silane Chemical class CO[Si](OC)(OC)C1CCC=CC1 JSAXPYDTIXIPSX-UHFFFAOYSA-N 0.000 description 3
- DEXQAPXXCAGFOD-UHFFFAOYSA-N cyclopent-2-en-1-yl(trihydroxy)silane Chemical compound O[Si](O)(O)C1CCC=C1 DEXQAPXXCAGFOD-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VQGTUOAFHTUMQG-UHFFFAOYSA-N C1(C=CCC1)[Si](O)(O)C Chemical compound C1(C=CCC1)[Si](O)(O)C VQGTUOAFHTUMQG-UHFFFAOYSA-N 0.000 description 2
- JSFSEDILFQLLIL-UHFFFAOYSA-N C12C(CC(C=C1)CC2)[Si](O)(O)C Chemical compound C12C(CC(C=C1)CC2)[Si](O)(O)C JSFSEDILFQLLIL-UHFFFAOYSA-N 0.000 description 2
- OOIKCUZYRXCTOY-UHFFFAOYSA-N C12C(CC(C=C1)CC2)[Si](O)(O)O Chemical compound C12C(CC(C=C1)CC2)[Si](O)(O)O OOIKCUZYRXCTOY-UHFFFAOYSA-N 0.000 description 2
- GWUAZKFYJQVEGC-UHFFFAOYSA-N C1CC(CC=C1)[Si](O)(O)O Chemical compound C1CC(CC=C1)[Si](O)(O)O GWUAZKFYJQVEGC-UHFFFAOYSA-N 0.000 description 2
- MGHYJVGOLDYEOM-UHFFFAOYSA-N CC1=C(CC(CC1)[Si](C)(OC)OC)C Chemical compound CC1=C(CC(CC1)[Si](C)(OC)OC)C MGHYJVGOLDYEOM-UHFFFAOYSA-N 0.000 description 2
- TYIPAEPIJZIKOI-UHFFFAOYSA-N CC1=CCC(CC1)[Si](OC)(OC)OC Chemical class CC1=CCC(CC1)[Si](OC)(OC)OC TYIPAEPIJZIKOI-UHFFFAOYSA-N 0.000 description 2
- YYCGVJVXCNNXEB-UHFFFAOYSA-N C[Si](C1CCC=CC1)(O)O Chemical compound C[Si](C1CCC=CC1)(O)O YYCGVJVXCNNXEB-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- OTCDSKUZNNQRFT-UHFFFAOYSA-N cyclohex-3-en-1-yl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCC=CC1 OTCDSKUZNNQRFT-UHFFFAOYSA-N 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- VITZEQDXVHSWTJ-UHFFFAOYSA-N cyclohexyl(trihydroxy)silane Chemical compound O[Si](O)(O)C1CCCCC1 VITZEQDXVHSWTJ-UHFFFAOYSA-N 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NWOKQWFBSXOISW-UHFFFAOYSA-N trihydroxy-(4-methylcyclohex-3-en-1-yl)silane Chemical class CC1=CCC([Si](O)(O)O)CC1 NWOKQWFBSXOISW-UHFFFAOYSA-N 0.000 description 2
- QRRBMOPGYOJPMO-UHFFFAOYSA-N (3,4-dimethylcyclohex-3-en-1-yl)-trihydroxysilane Chemical compound CC1=C(C)CC([Si](O)(O)O)CC1 QRRBMOPGYOJPMO-UHFFFAOYSA-N 0.000 description 1
- LYFYDCJTJNPHET-UHFFFAOYSA-N C1(C=CCC1)[Si](O[Si](O)(O)C1C=CCC1)(O)O Chemical compound C1(C=CCC1)[Si](O[Si](O)(O)C1C=CCC1)(O)O LYFYDCJTJNPHET-UHFFFAOYSA-N 0.000 description 1
- HTZOJYTWZNGUFY-UHFFFAOYSA-N C12C(CC(C=C1)CC2)[Si](OCC)(OCC)OCC Chemical compound C12C(CC(C=C1)CC2)[Si](OCC)(OCC)OCC HTZOJYTWZNGUFY-UHFFFAOYSA-N 0.000 description 1
- GOUYBXSXMFGQJI-UHFFFAOYSA-N CC1=C(CC(CC1)[Si](C)(O)O)C Chemical compound CC1=C(CC(CC1)[Si](C)(O)O)C GOUYBXSXMFGQJI-UHFFFAOYSA-N 0.000 description 1
- YOXVZRYQIKSNSE-UHFFFAOYSA-N CC1=CCC(CC1)CCO[SiH3] Chemical compound CC1=CCC(CC1)CCO[SiH3] YOXVZRYQIKSNSE-UHFFFAOYSA-N 0.000 description 1
- KLHXTDHHMWXNLX-UHFFFAOYSA-N CC1=CCC(CC1)CO[SiH3] Chemical compound CC1=CCC(CC1)CO[SiH3] KLHXTDHHMWXNLX-UHFFFAOYSA-N 0.000 description 1
- GEEWCCFVYQMRRZ-UHFFFAOYSA-N CCO[Si](C1CCC(=C(C1)C)C)(OCC)OCC Chemical compound CCO[Si](C1CCC(=C(C1)C)C)(OCC)OCC GEEWCCFVYQMRRZ-UHFFFAOYSA-N 0.000 description 1
- IZFDHJQLRXTKJH-UHFFFAOYSA-N CO[Si](C)(C1CCCC=C1)OC Chemical compound CO[Si](C)(C1CCCC=C1)OC IZFDHJQLRXTKJH-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- MEWFSXFFGFDHGV-UHFFFAOYSA-N cyclohexyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CCCCC1 MEWFSXFFGFDHGV-UHFFFAOYSA-N 0.000 description 1
- OWHBXDNDNVFEEU-UHFFFAOYSA-N cyclopent-2-en-1-yl(triethoxy)silane Chemical class CCO[Si](OCC)(OCC)C1CCC=C1 OWHBXDNDNVFEEU-UHFFFAOYSA-N 0.000 description 1
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 1
- GLKIVPZUGYORGG-UHFFFAOYSA-N dihydroxysilyloxy(dihydroxy)silane Chemical compound O[SiH](O)O[SiH](O)O GLKIVPZUGYORGG-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZJBHFQKJEBGFNL-UHFFFAOYSA-N methylsilanetriol Chemical compound C[Si](O)(O)O ZJBHFQKJEBGFNL-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- KCIKCCHXZMLVDE-UHFFFAOYSA-N silanediol Chemical compound O[SiH2]O KCIKCCHXZMLVDE-UHFFFAOYSA-N 0.000 description 1
- 229940089952 silanetriol Drugs 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ZDGAYUONHCLPJN-UHFFFAOYSA-N trichloro-(1-trimethylsilylcyclopenta-2,4-dien-1-yl)silane Chemical compound C[Si](C)(C)C1([Si](Cl)(Cl)Cl)C=CC=C1 ZDGAYUONHCLPJN-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- FCVNATXRSJMIDT-UHFFFAOYSA-N trihydroxy(phenyl)silane Chemical compound O[Si](O)(O)C1=CC=CC=C1 FCVNATXRSJMIDT-UHFFFAOYSA-N 0.000 description 1
- NNVBLXFMHTYCJQ-UHFFFAOYSA-N trihydroxy-(1-trimethylsilylcyclopenta-2,4-dien-1-yl)silane Chemical compound C[Si](C)(C)C1([Si](O)(O)O)C=CC=C1 NNVBLXFMHTYCJQ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 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
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
Description
Claims (4)
- 다음 화학식 2로 표시되는 유기실란 화합물을 0.1 ~ 10 중량% 농도의 초산 수용액을 사용하여, 0 ~ 40 ℃의 온도 범위에서 가수분해 반응시켜 제조한 것을 특징으로 하는 다음 화학식 1로 표시되는 시클로알케닐실란폴리올 유도체의 제조방법:[화학식 2][화학식 1]상기 화학식 1과 2에서,R은 2-시클로펜테닐, 3-시클로헥센닐, 3- 또는 4-메틸시클로헥사-3-엔닐의 이성질체 혼합물, 3,4-디메틸시클로헥사-3-엔닐 및 바이시클로[2,2,2]옥타-5-엔-2-일 중에서 선택되며, R'은 C1 ~ 6의 알킬기 , X는 C1 ~ 6의 알킬기 , C1 ~ 6의 알콕시기 중에서 선택되고, Y는 수산기, 및 ((2-시클로펜테닐)디하이드록시실릴)옥시기 중에서 선택된다.
- 삭제
- 삭제
Priority Applications (1)
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KR1020070106843A KR100979461B1 (ko) | 2007-10-23 | 2007-10-23 | 시클로알케닐실란폴리올 유도체와 이의 제조방법 |
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KR1020070106843A KR100979461B1 (ko) | 2007-10-23 | 2007-10-23 | 시클로알케닐실란폴리올 유도체와 이의 제조방법 |
Publications (2)
Publication Number | Publication Date |
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KR20090041242A KR20090041242A (ko) | 2009-04-28 |
KR100979461B1 true KR100979461B1 (ko) | 2010-09-02 |
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KR1020070106843A KR100979461B1 (ko) | 2007-10-23 | 2007-10-23 | 시클로알케닐실란폴리올 유도체와 이의 제조방법 |
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Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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KR101152663B1 (ko) * | 2009-10-28 | 2012-06-15 | 한국과학기술연구원 | 기능성 보강 충전제 및 이의 제조 방법 |
KR101250300B1 (ko) * | 2011-04-29 | 2013-04-03 | 한국과학기술연구원 | 알케닐알콕시실란을 이용한 기능성 보강 충전제 및 이의 제조 방법 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5017695A (en) * | 1987-12-03 | 1991-05-21 | Rhone-Poulenc, Inc. | Ceric hydrocarbyl silyloxides and process for their preparation |
KR100757068B1 (ko) * | 2006-04-21 | 2007-09-10 | 한국과학기술연구원 | (시클로펜테닐)알킬디알콕시실란 유도체와 그의 제조방법 |
-
2007
- 2007-10-23 KR KR1020070106843A patent/KR100979461B1/ko active IP Right Grant
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5017695A (en) * | 1987-12-03 | 1991-05-21 | Rhone-Poulenc, Inc. | Ceric hydrocarbyl silyloxides and process for their preparation |
KR100757068B1 (ko) * | 2006-04-21 | 2007-09-10 | 한국과학기술연구원 | (시클로펜테닐)알킬디알콕시실란 유도체와 그의 제조방법 |
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KR20090041242A (ko) | 2009-04-28 |
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