CA1215716A - Monoaldehyde containing hydrolyzable silanes - Google Patents
Monoaldehyde containing hydrolyzable silanesInfo
- Publication number
- CA1215716A CA1215716A CA000423394A CA423394A CA1215716A CA 1215716 A CA1215716 A CA 1215716A CA 000423394 A CA000423394 A CA 000423394A CA 423394 A CA423394 A CA 423394A CA 1215716 A CA1215716 A CA 1215716A
- Authority
- CA
- Canada
- Prior art keywords
- radical
- silane
- alkylene
- formula
- hch3
- 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.)
- Expired
Links
- 150000004756 silanes Chemical class 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 24
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 22
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 3
- 229910000077 silane Inorganic materials 0.000 claims description 45
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 44
- -1 alkoxy radical Chemical class 0.000 claims description 36
- 150000003254 radicals Chemical class 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
- 239000010948 rhodium Substances 0.000 claims description 13
- 229910052703 rhodium Inorganic materials 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 9
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical group CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 8
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 abstract description 22
- 239000007858 starting material Substances 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000007822 coupling agent Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 description 45
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 24
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 24
- 239000000047 product Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003172 aldehyde group Chemical group 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001793 charged compounds Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241000518994 Conta Species 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000006315 carbonylation Effects 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 2
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-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
- OBWGMYALGNDUNM-UHFFFAOYSA-N 3,3-dimethoxyprop-1-ene Chemical compound COC(OC)C=C OBWGMYALGNDUNM-UHFFFAOYSA-N 0.000 description 1
- YNORIRQJELXXGZ-UHFFFAOYSA-N 3,3-dimethoxypropyl(trimethoxy)silane Chemical compound COC(OC)CC[Si](OC)(OC)OC YNORIRQJELXXGZ-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- 101100139852 Danio rerio radil gene Proteins 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000286904 Leptothecata Species 0.000 description 1
- 101100139854 Mus musculus Radil gene Proteins 0.000 description 1
- 241001315609 Pittosporum crassifolium Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 150000001723 carbon free-radicals Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 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
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-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
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000000543 intermediate Substances 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
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 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
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-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
- C07F7/18—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 |
|---|---|---|---|
| US361,189 | 1982-03-24 | ||
| US06/361,189 US4424392A (en) | 1982-03-24 | 1982-03-24 | Aldehyde containing hydrolyzable silanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1215716A true CA1215716A (en) | 1986-12-23 |
Family
ID=23421019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000423394A Expired CA1215716A (en) | 1982-03-24 | 1983-03-11 | Monoaldehyde containing hydrolyzable silanes |
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) |
Families Citing this family (23)
| 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 |
| FR2636067B1 (fr) * | 1988-09-05 | 1990-05-18 | Rhone Poulenc Chimie | Polyorganosiloxane a fonction propanaldehyde et son procede de preparation par hydroformylation |
| FR2645867B1 (fr) * | 1989-04-13 | 1991-06-14 | Rhone Poulenc Chimie | Procede de preparation, par hydroformylation, de polyorganosiloxane a fonction propanaldehyde |
| FR2647801B1 (fr) * | 1989-06-02 | 1991-09-13 | Rhone Poulenc Chimie | Composition durcissable, sous un rayonnement, a base de polyorganosiloxane a fonction propanaldehyde |
| 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 |
| BR112013026805B1 (pt) * | 2011-04-18 | 2020-05-26 | Momentive Perfomance Materials Gmbh | Uso de poliorganossiloxanos ou silanos para o tratamento de materiais lignocelulósicos, uso de composições compreendendo pelo menos um polissiloxano e/ou silano, composições, processo para o tratamento de material lignocelulósico, uso de pelo menos um polissiloxano e/ou silano e material lignocelulósico |
| CN116261565A (zh) * | 2020-10-13 | 2023-06-13 | 美国陶氏有机硅公司 | 具有醛官能团的有机硅化合物的制备 |
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58172394A (ja) | 1983-10-11 |
| 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 |
| EP0183280A2 (en) | 1986-06-04 |
| EP0183280A3 (en) | 1988-06-08 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |