JPS58172394A - アルデヒド含有加水分解可能なシラン及びその製造法 - Google Patents
アルデヒド含有加水分解可能なシラン及びその製造法Info
- Publication number
- JPS58172394A JPS58172394A JP58047346A JP4734683A JPS58172394A JP S58172394 A JPS58172394 A JP S58172394A JP 58047346 A JP58047346 A JP 58047346A JP 4734683 A JP4734683 A JP 4734683A JP S58172394 A JPS58172394 A JP S58172394A
- Authority
- JP
- Japan
- Prior art keywords
- group
- silane
- aldehyde
- silane according
- formula
- 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.)
- Pending
Links
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims description 58
- 229910000077 silane Inorganic materials 0.000 title claims description 58
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000007037 hydroformylation reaction Methods 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- -1 methoxy ethoxy group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 229910002090 carbon oxide Inorganic materials 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 125000004956 cyclohexylene group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 description 48
- 239000000203 mixture Substances 0.000 description 36
- 150000004756 silanes Chemical class 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 15
- 239000000047 product Substances 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 10
- 238000004817 gas chromatography Methods 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000010948 rhodium Substances 0.000 description 10
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 10
- 229910052703 rhodium Inorganic materials 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000009102 absorption Effects 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 125000003172 aldehyde group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 238000004611 spectroscopical analysis Methods 0.000 description 4
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000001793 charged compounds Chemical class 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- OHBTULDTCSOWOY-UHFFFAOYSA-N [C].C=C Chemical group [C].C=C OHBTULDTCSOWOY-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- MXVLMYZRJAHEIS-UHFFFAOYSA-N 1-(2-phenylphenyl)naphthalene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 MXVLMYZRJAHEIS-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- LSUMROSSVWBUMR-UHFFFAOYSA-N 2-trimethylsilylpropanal Chemical class O=CC(C)[Si](C)(C)C LSUMROSSVWBUMR-UHFFFAOYSA-N 0.000 description 1
- KJXJKBSJOFRRBT-UHFFFAOYSA-N 3-methylbut-2-en-2-ylsilane Chemical compound CC(C)=C(C)[SiH3] KJXJKBSJOFRRBT-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 208000031968 Cadaver Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 241001315609 Pittosporum crassifolium Species 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FRYDSOYOHWGSMD-UHFFFAOYSA-N [C].O Chemical compound [C].O FRYDSOYOHWGSMD-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- FIMRGWGERKDGSV-UHFFFAOYSA-N methyl 2-methylprop-2-enoate prop-1-ene Chemical compound COC(C(=C)C)=O.C=CC FIMRGWGERKDGSV-UHFFFAOYSA-N 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US361189 | 1982-03-24 | ||
| US06/361,189 US4424392A (en) | 1982-03-24 | 1982-03-24 | Aldehyde containing hydrolyzable silanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58172394A true JPS58172394A (ja) | 1983-10-11 |
Family
ID=23421019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58047346A Pending JPS58172394A (ja) | 1982-03-24 | 1983-03-23 | アルデヒド含有加水分解可能なシラン及びその製造法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4424392A (cg-RX-API-DMAC10.html) |
| EP (2) | EP0089690A1 (cg-RX-API-DMAC10.html) |
| JP (1) | JPS58172394A (cg-RX-API-DMAC10.html) |
| AU (1) | AU556855B2 (cg-RX-API-DMAC10.html) |
| BR (1) | BR8301357A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1215716A (cg-RX-API-DMAC10.html) |
| IN (1) | IN158046B (cg-RX-API-DMAC10.html) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02107640A (ja) * | 1988-09-05 | 1990-04-19 | Rhone Poulenc Chim | プロパンアルデヒド官能基含有ポリオルガノシロキサン及びヒドロホルミル化によるその製造方法 |
| JPH02296830A (ja) * | 1989-04-13 | 1990-12-07 | Rhone Poulenc Chim | ヒドロホルミル化によるプロパンアルデヒド官能基を含有するポリオルガノシロキサンの製造方法 |
| JPH0372514A (ja) * | 1989-06-02 | 1991-03-27 | Rhone Poulenc Chim | プロパンアルデヒド官能基を含有するポリオルガノシロキサンをベースにした、放射線を受けて硬化させることができる組成物 |
| CN103764725A (zh) * | 2011-04-18 | 2014-04-30 | 迈图高新材料有限责任公司 | 用于处理木质纤维素材料的官能化的聚有机硅氧烷或硅烷 |
| JP2023547349A (ja) * | 2020-10-13 | 2023-11-10 | ダウ シリコーンズ コーポレーション | アルデヒド官能基を有するオルガノケイ素化合物の調製 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5988737A (ja) * | 1982-11-15 | 1984-05-22 | Hitachi Ltd | 放射線感応性有機高分子材料 |
| US4571428A (en) * | 1983-07-08 | 1986-02-18 | Sandoz, Inc. | 6-Substituted-4-hydroxy-tetrahydropyran-2-ones |
| US5124468A (en) * | 1991-08-02 | 1992-06-23 | General Electric Company | Method for silylformylating alkynes and products obtained therefrom |
| WO1994017080A1 (en) * | 1993-01-26 | 1994-08-04 | Utah State University | Rhodium catalyzed silaformylation of aldehydes and products obtained therefrom |
| US5300375A (en) * | 1993-04-19 | 1994-04-05 | Valence Technology, Inc. | Acrylic alkoxy silane monomer and solid electrolyte derived by the polymerization thereof |
| CO4410239A1 (es) * | 1993-06-21 | 1997-01-09 | Atochem North America Elf | Un metodo para el fortalecimiento de un sustrato de oxido fragil, composiciones de silano, y un sustrato de oxido fragil recubierto con siloxano de enlace cruzado polimerizado |
| US5880304A (en) * | 1997-03-06 | 1999-03-09 | Dow Corning Corporation | Method of making organosilicon carbonyl compounds |
| US6365646B1 (en) | 1999-12-08 | 2002-04-02 | Borden Chemical, Inc. | Method to improve humidity resistance of phenolic urethane foundry binders |
| DE10233936A1 (de) * | 2002-07-25 | 2004-02-12 | Wacker Polymer Systems Gmbh & Co. Kg | Silan-haltige Polymerisate |
| KR20240074835A (ko) | 2021-10-06 | 2024-05-28 | 다우 글로벌 테크놀로지스 엘엘씨 | 아미노-작용성 유기규소 화합물의 제조 |
| WO2023060155A1 (en) | 2021-10-06 | 2023-04-13 | Dow Global Technologies Llc | Preparation of propylimine-functional organosilicon compounds and primary aminopropyl-functional organosilicon compounds |
| US20250122229A1 (en) | 2021-11-22 | 2025-04-17 | Dow Silicones Corporation | Preparation of organosilicon compounds with carbinol functionality |
| WO2023183682A1 (en) | 2022-03-21 | 2023-09-28 | Dow Global Technologies Llc | Preparation of organosilicon compounds with carboxy functionality |
| US20250215162A1 (en) | 2022-04-13 | 2025-07-03 | Dow Global Technologies Llc | Preparation of polyether-functional organosilicon compounds |
| KR20250021433A (ko) | 2022-04-13 | 2025-02-13 | 다우 글로벌 테크놀로지스 엘엘씨 | 비닐에스테르 관능성을 갖는 유기규소 화합물의 제조 |
| WO2025193391A1 (en) | 2024-03-12 | 2025-09-18 | Dow Global Technologies Llc | Curable aldehyde – aminosiloxane ester composition and method for its preparation |
| WO2025254797A1 (en) | 2024-06-04 | 2025-12-11 | Dow Global Technologies Llc | Aldehyde – diamine curable polyorganosiloxane composition and methods for the preparation and use thereof |
| WO2025254798A1 (en) | 2024-06-04 | 2025-12-11 | Dow Global Technologies Llc | Aldehyde – amine curable polyorganosiloxane composition and methods for the preparation and use thereof |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2588083A (en) | 1950-06-01 | 1952-03-04 | Gen Electric | Organosilicon aldehydes and methods of preparing the same |
| US2641605A (en) | 1952-05-15 | 1953-06-09 | Gen Electric | Triorganosilylbenzaldehydes |
| US3099670A (en) | 1953-12-31 | 1963-07-30 | Gen Electric | Addition of silicon hydrides to aliphatically unsaturated organic compounds |
| US2803637A (en) | 1954-01-18 | 1957-08-20 | Dow Corning | Organosiloxane aldehydes |
| US2805236A (en) | 1955-03-28 | 1957-09-03 | Union Carbide Corp | 2, 4-di (formyl) cyclopentyltriorganosilanes and process for their preparation |
| US2989559A (en) | 1958-06-27 | 1961-06-20 | Union Carbide Corp | Carbonyl-containing organopolysiloxanes |
| FR1301109A (fr) * | 1961-08-23 | 1962-08-10 | Goldschmidt Ag Th | Procédé pour la préparation de siloxaalcanes cycliques et polymères |
| US3168553A (en) | 1961-08-25 | 1965-02-02 | Shell Oil Co | Reactions of olefins with carbon monoxide |
| US3527809A (en) | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| US3824278A (en) | 1972-03-23 | 1974-07-16 | Sandoz Ag | 1,6-disubstituted pyrocatechol derivatives |
| US4002651A (en) | 1974-06-26 | 1977-01-11 | Union Carbide Corporation | Azido-silane compositions |
-
1982
- 1982-03-24 US US06/361,189 patent/US4424392A/en not_active Expired - Lifetime
-
1983
- 1983-03-11 CA CA000423394A patent/CA1215716A/en not_active Expired
- 1983-03-18 BR BR8301357A patent/BR8301357A/pt unknown
- 1983-03-21 AU AU12635/83A patent/AU556855B2/en not_active Ceased
- 1983-03-23 EP EP83102886A patent/EP0089690A1/en not_active Withdrawn
- 1983-03-23 JP JP58047346A patent/JPS58172394A/ja active Pending
- 1983-03-23 IN IN348/CAL/83A patent/IN158046B/en unknown
- 1983-03-23 EP EP85116531A patent/EP0183280A3/en not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| AZERB. KHIM. ZH.=1966 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02107640A (ja) * | 1988-09-05 | 1990-04-19 | Rhone Poulenc Chim | プロパンアルデヒド官能基含有ポリオルガノシロキサン及びヒドロホルミル化によるその製造方法 |
| JPH02296830A (ja) * | 1989-04-13 | 1990-12-07 | Rhone Poulenc Chim | ヒドロホルミル化によるプロパンアルデヒド官能基を含有するポリオルガノシロキサンの製造方法 |
| JPH0372514A (ja) * | 1989-06-02 | 1991-03-27 | Rhone Poulenc Chim | プロパンアルデヒド官能基を含有するポリオルガノシロキサンをベースにした、放射線を受けて硬化させることができる組成物 |
| CN103764725A (zh) * | 2011-04-18 | 2014-04-30 | 迈图高新材料有限责任公司 | 用于处理木质纤维素材料的官能化的聚有机硅氧烷或硅烷 |
| CN103764725B (zh) * | 2011-04-18 | 2017-03-01 | 迈图高新材料有限责任公司 | 用于处理木质纤维素材料的官能化的聚有机硅氧烷或硅烷 |
| JP2023547349A (ja) * | 2020-10-13 | 2023-11-10 | ダウ シリコーンズ コーポレーション | アルデヒド官能基を有するオルガノケイ素化合物の調製 |
Also Published As
| Publication number | Publication date |
|---|---|
| US4424392A (en) | 1984-01-03 |
| AU1263583A (en) | 1983-09-29 |
| BR8301357A (pt) | 1983-11-29 |
| IN158046B (cg-RX-API-DMAC10.html) | 1986-08-23 |
| EP0089690A1 (en) | 1983-09-28 |
| AU556855B2 (en) | 1986-11-20 |
| CA1215716A (en) | 1986-12-23 |
| EP0183280A2 (en) | 1986-06-04 |
| EP0183280A3 (en) | 1988-06-08 |
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