DE1262271B - Verfahren zur Herstellung von Organosiliciumverbindungen - Google Patents
Verfahren zur Herstellung von OrganosiliciumverbindungenInfo
- Publication number
- DE1262271B DE1262271B DED49976A DED0049976A DE1262271B DE 1262271 B DE1262271 B DE 1262271B DE D49976 A DED49976 A DE D49976A DE D0049976 A DED0049976 A DE D0049976A DE 1262271 B DE1262271 B DE 1262271B
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- organosilicon compounds
- radicals
- platinum
- average values
- 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
- 150000003961 organosilicon compounds Chemical class 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 16
- 229910052697 platinum Inorganic materials 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 10
- FSIJKGMIQTVTNP-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C=C)C=C FSIJKGMIQTVTNP-UHFFFAOYSA-N 0.000 description 3
- -1 polysiloxanes Polymers 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910004283 SiO 4 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Chemical class CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 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
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- 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
- C07F7/0801—General processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/828—Platinum
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Silicon Polymers (AREA)
Description
DEUTSCHES
PATENTAMT
Int. CL:
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:
Aktenzeichen:
Anmeldetag:
Auslegetag:
C07f
C 08 g
D49976IVb/12o
28. April 1966
7. März 1968
28. April 1966
7. März 1968
Zahlreiche Verbindungen, die = SiH-Gruppen enthalten,
können mit Verbindungen, die aliphatische Mehrfachbindungen enthalten, in Gegenwart von
Platinverbindungen, wie Chlorplatinsäure, umgesetzt werden. Derartige Umsetzungen werden in der deutschen
Patentschrift 1069148 ausführlich erläutert. Ein Beispiel hierfür ist die Umsetzung nach folgendem
Schema:
Verfahren zur Herstellung
von Organosiliciumverbindungen
CH3
HSiCl2
HSiCl2
CH =
CH3
CH2CH2SiCl2
Erfindungsgemäß werden bei Verfahren zur Herstellung von Organosiliciumverbindungen durch Umsetzung
von Si—Η-Verbindungen mit aliphatisch ungesättigten Verbindungen in Gegenwart von Platinkatalysatoren
als Platinkatalysatoren Umsetzungsprodukte von Hexachloroplatinsäure (1) mit mindestens
einer Organosiliciumverbindung (2), die im wesentlichen aus Einheiten der allgemeinen Formel
R„SiO4_fl_„
aufgebaut ist, worin R ein einwertiger, gegebenenfalls halogenierter Kohlenwasserstoffrest ist, wobei mindestens
einer der Reste R eine endständige aliphatische Mehrfachbindung enthält, und X einen hydrolysierbaren
Rest bedeutet sowie η Durchschnittswerte von 1,5 bis 4, m Durchschnittswerte von 1 bis 20
und α Durchschnittswerte von 0 bis 2,5 haben, verwendet.
Die erfindungsgemäß verwendbaren Katalysatoren zeigen eine ausgezeichnete Verträglichkeit mit Organosiliciumverbindungen;
deshalb ist bei Einsatz der erfindungsgemäßen Katalysatoren für die obengenannten
Umsetzungen weniger Platin erforderlich als bei Einsatz von Platin in Form von Hexachloroplatinsäure
oder platinierter Kohle. Bei Einsatz der erfindungsgemäßen Katalysatoren verlaufen diese Umsetzungen
rascher als bei Einsatz gleicher Mengen an Platin in Form von Hexachlorplatinsäure. Außerdem
neigen Katalysatoren, wie Hexachloroplatinsäure, auf Grund ihrer allgemeinen Unverträglich-Anmelder:
Dow Corning Corporation,
Midland, Mich. (V. St. A.)
Vertreter:
Dr. B. Pass, Rechtsanwalt,
8000 München 22, Von-der-Tann-Str. 14
Als Erfinder benannt:
David Nelson Willing,
Midland, Mich. (V. St. A.)
David Nelson Willing,
Midland, Mich. (V. St. A.)
Beanspruchte Priorität:
V. St. v. Amerika vom 17. Mai 1965 (456 516)
keit mit Organosiliciumverbindungen dazu, das Reäktionsmedium zu verdicken. Diese mögliche unerwünschte
Nebenwirkung wird durch Einsatz der erfindungsgemäßen Katalysatoren vermieden, die zudem
den Vorteil haben, daß sie im allgemeinen flüssig und niedrig viskos sind.
Beispiele für einwertige Kohlenwasserstoffreste R in den Organosiliciumverbindungen (2) sind Alkyl-
und Cycloalkylreste, aliphatisch ungesättigte Reste und Arylgruppen enthaltende Reste sowie die entsprechenden
halogenierten Reste.
Der Index η hat vorzugsweise Durchschnittswerte von 1,5 bis 3.
Unter hydrolysierbaren Gruppen X sind beliebige Si-gebundene Reste zu verstehen, die mit Wasser
unterhalb von 1000C unter Bildung von Silanolgruppen reagieren, z. B. Alkoxygruppen, Acyloxygruppen,
Halogenatome und Ketoximderivate.
Die erfindungsgemäß verwendbaren Katalysatoren können durch einfaches Erhitzen von Hexachloroplatinsäure
mit den Organosiliciumverbindungen (2) auf etwa 20 bis 1500C hergestellt werden.
Die genaue Struktur dieser Umsetzungsprodukte ist nicht bekannt. Es wird angenommen,' daß die
Hexachloroplatinsäure mit den aliphatisch ungesättigten Resten R der Organosiliciumverbindungen
einen Komplex bildet.
809 517/732
Vorzugsweise sollte auf jedes vorhandene Platinatom mindestens ein Rest R mit endständiger Mehrfachbindung
vorhanden sein. Die Verwendung eines zweifachen molaren Überschusses oder mehr an
endständigen aliphatischen Mehrfachbindungen ist besonders vorteilhaft, da der Platinkatalysator in
sehr geringen Konzentrationen wirksam ist. Durch einen derartigen molaren Überschuß wird garantiert,
daß alle vorhandenen Platinatome komplex gebunden werden, eine Verschwendung von Platin wird so
vermieden.
Als ungesättigte Reste R werden Vinylreste bevorzugt; besonders bevorzugt sind Organosiliciumverbindungen
(2), die mindestens zwei Vinylgruppen je Molekül Hexachloroplatinsäure besitzen.
Die Organosiliciumverbindung (2) kann ein Homopolymerisat oder ein Mischpolymerisat sein. Sie
kann aber auch ein Silan sein, jedoch werden Polysiloxane bevorzugt. Sie kann außerdem geringe
Mengen Si-gebundene Wasserstoffatome oder Hydroxylgruppen enthalten.
Die Auswahl der günstigsten Organosiliciumverbindungen (2) ist von der Art der Reaktion abhängig,
für welche der Katalysatorkomplex eingesetzt wird.
Als erfindungsgemäß verwendbare Katalysatoren werden Umsetzungsprodukte aus Hexachloroplatinsäure
mit Organosiliciumverbindungen (2) der Formel B ei s ρ i el 1
Ein Gemisch aus 159 g destilliertem sym. Divinyltetramethyldisiloxan
und 3,2 g H2PtCl6 · 6H2O wurde
unter Rühren 1 Stunde auf 120° C erhitzt. Anschließend wurde das Reaktionsgemisch abgekühlt und mit
g sym. Divinyltetramethyldisiloxan verdünnt. Nach dem Abfiltrieren wurde ein klares, sauer reagierendes,
leicht gelbgefärbtes, flüssiges Produkt erhalten. Die Azidität wurde durch Waschen mit Wasser
entfernt.
Eine Spur dieser neutralen Flüssigkeit wurde einem Gemisch aus
(CH3J3SiO
CH3
SiO
SiO
-Si(CH3J3
und
CH, = CH
SiO
CH3
CH3
CH,
— SiCH = CH2 CH3
CH3
CH7 = CHSiO
CH7 = CHSiO
CH, R'
CH3
SiO
SiO
CH3 OSiCH = CH,
CH,
worin R' einwertige, gegebenenfalls halogenierte Kohlenwasserstoffreste
bedeutet und χ eine ganze Zahl von 3 bis 6 ist, bevorzugt.
Die Verträglichkeitseigenschaften des Umsetzungsproduktes können durch Einsatz verschiedener
Reste R' unterschiedlichen Bedingungen angepaßt werden; Beispiele für Reste R' sind Methyl-, Octadecyl-,
Phenyl- oder 3,3,3-Trifluorpropylreste, wobei die beiden letztgenannten Reste bevorzugt sind.
Die angeführten Siloxane können durch Äquilibrierung
von sym. Divinyltetramethyldisiloxan mit einem cyclischen Siloxan der Formel unter leichtem Erhitzen zugegeben; es wurde ein Gel
gebildet, was darauf hinweist, daß die bekannte Reaktion zwischen der = SiH- und der CH2 = CH-Bindung
stattgefunden hat.
Beispiel 2
0,1 g Chlorplatinsäure wurde mit 20 g
35 CH2 = CHSi(CH3I2O[Si(CH3)
45
CH3
SiO-
SiO-
R'
worin R' und χ die angegebene Bedeutung haben, in einem alkalischen Medium hergestellt werden.
Die erfindungsgemäß verwendbaren Katalysatoren zeigen bei der Umsetzung von SiH-Bindungen mit
Olefinen oder Olefinderivaten eine katalytische Aktivität, die etwa der Konzentration an vorhandenem
Platin proportional ist. Eine katalytische Menge an Platin ist alles, was für den Reaktionsablauf
erforderlich ist. Im allgemeinen ist es für eine ausreichende vorhandene Katalysatormenge für die Umsetzungen
von SiH-Bindungen mit aliphatisch ungesättigten Bindungen vorteilhaft, wenn im Reaktionsgemisch mindestens 1 · 10~8 Mol Platin je Äquivalent
der aliphatischen Mehrfachbindung vorhanden sind.
= CH2
auf 10O0C erhitzt bis zur Bildung eines homogenen
Produktes. Dieses Produkt war ein kräftiger Katalysator für die Umsetzung von = SiH-Bindungen mit
aliphatisch ungesättigten Bindungen.
Claims (1)
- Patentanspruch:Verfahren zur Herstellung von Organosiliciumverbindungen durch Umsetzung von Si—H-Verbindungen mit aliphatisch ungesättigten Verbindungen in Gegenwart von Platinkatalysatoren, dadurch gekennzeichnet, daß als Platinkatalysatoren Umsetzungsprodukte von Hexachloroplatinsäure (1) mit mindestens einer Organosiliciumverbindung (2), die im wesentlichen aus Einheiten der allgemeinen Formel505560 R„SiO,_„_aufgebaut ist, worin R ein einwertiger, gegebenenfalls halogenierter Kohlenwasserstoffrest ist, wobei mindestens einer der Reste JR eine endständige aliphatische Mehrfachbindung enthält und X einen hydrolysierbaren Rest bedeutet, sowie η Durchschnittswerte von 1,5 bis 4, m Durchschnittswerte von 1 bis 20 und α Durchschnittswerte von O bis 2,5 haben, verwendet werden.809 517/732 2.68 © Bundesdruckerei Berlin
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US456516A US3419593A (en) | 1965-05-17 | 1965-05-17 | Catalysts for the reaction of = sih with organic compounds containing aliphatic unsaturation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1262271B true DE1262271B (de) | 1968-03-07 |
Family
ID=23813075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED49976A Pending DE1262271B (de) | 1965-05-17 | 1966-04-28 | Verfahren zur Herstellung von Organosiliciumverbindungen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3419593A (de) |
| DE (1) | DE1262271B (de) |
| GB (1) | GB1127675A (de) |
| NL (2) | NL6606771A (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1668159A1 (de) * | 1966-12-01 | 1971-09-02 | Gen Electric | Organosiliziummaterialien und Verfahren zu ihrer Herstellung |
| EP2835403A1 (de) | 2013-08-06 | 2015-02-11 | HILTI Aktiengesellschaft | Dämmschichtbildende Zusammensetzung und deren Verwendung |
Families Citing this family (673)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3516946A (en) * | 1967-09-29 | 1970-06-23 | Gen Electric | Platinum catalyst composition for hydrosilation reactions |
| US3530092A (en) * | 1968-07-26 | 1970-09-22 | Union Carbide Corp | Process for preparing organosiliconnitrogen compounds |
| US3715334A (en) * | 1970-11-27 | 1973-02-06 | Gen Electric | Platinum-vinylsiloxanes |
| US3723497A (en) * | 1971-11-19 | 1973-03-27 | Dow Corning | Silicone compositions catalyzed with platinum ii diacetylacetonate |
| US3950300A (en) * | 1972-10-11 | 1976-04-13 | Wacker-Chemie Gmbh | Dental impression materials |
| US3933882A (en) * | 1974-12-02 | 1976-01-20 | Dow Corning Corporation | Tube method for the preparation of olefinic siloxane compounds |
| US3933880A (en) * | 1974-12-02 | 1976-01-20 | Dow Corning Corporation | Method of preparing a platinum catalyst inhibitor |
| US3971818A (en) * | 1974-12-02 | 1976-07-27 | Dow Corning Corporation | Method of preparing olefinic siloxane by GLC |
| JPS5277164A (en) * | 1975-12-24 | 1977-06-29 | Toshiba Silicone | Method of vulcanization of silicone rubber |
| DE2646726C2 (de) * | 1976-10-15 | 1988-07-28 | Wacker-Chemie GmbH, 8000 München | Die Anlagerung verzögerndes Mittel bei der durch Platinkatalysator geförderten und bei Raumtemperatur erfolgenden Anlagerung von Si-gebundenem Wasserstoff an mindestens 50 Si-Atome je Molekul und aliphatische Mehrfachbindungen enthaltendes Organopolysiloxan |
| US4288345A (en) * | 1980-02-06 | 1981-09-08 | General Electric Company | Platinum complex |
| US4357388A (en) * | 1980-11-13 | 1982-11-02 | International Business Machines Corporation | Hot roll fuser |
| US4511715A (en) * | 1981-03-20 | 1985-04-16 | Minnesota Mining And Manufacturing Company | Platinum-nitrogen complex catalysts |
| US4588800A (en) * | 1981-03-20 | 1986-05-13 | Minnesota Mining And Manufacturing Company | Platinum-nitrogen complex catalysts |
| DE3268643D1 (en) | 1981-08-14 | 1986-03-06 | Ici Plc | Catalysts |
| US4382057A (en) * | 1981-12-04 | 1983-05-03 | General Electric Company | Silicone rubber compositions for liquid injection molding machines |
| US4421903A (en) * | 1982-02-26 | 1983-12-20 | General Electric Company | Platinum complex catalysts |
| US4546164A (en) * | 1982-11-29 | 1985-10-08 | Sws Silicones Corporation | Process for preparing a one-component organopolysiloxane composition |
| US4433069A (en) * | 1983-01-03 | 1984-02-21 | Dow Corning Corporation | Method for preparing flame resistant polysiloxane foams and foams prepared thereby |
| US4533744A (en) * | 1983-08-29 | 1985-08-06 | General Electric Company | Hydrosilylation method, catalyst and method for making |
| JPS60152560A (ja) * | 1984-01-19 | 1985-08-10 | Shin Etsu Chem Co Ltd | 耐熱油性液状シリコ−ンゴム組成物 |
| DE3404703A1 (de) * | 1984-02-10 | 1985-09-05 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von 3-chlorpropyltrichlorsilan |
| DE3404702A1 (de) * | 1984-02-10 | 1985-09-05 | Degussa Ag, 6000 Frankfurt | Platin- und/oder palladium-haltige organopolysiloxan-ammoniumverbindungen, verfahren zu ihrer herstellung und verwendung |
| US4558109A (en) * | 1984-07-25 | 1985-12-10 | Sws Silicones Corporation | Curable organopolysiloxane compositions |
| US4631310A (en) * | 1984-08-20 | 1986-12-23 | Dow Corning Corporation | Platinum (O) alkyne complexes and a method for their preparation |
| US4562096A (en) | 1984-12-24 | 1985-12-31 | Dow Corning Corporation | Heat-curable silicone compositions, use thereof and stabilizer therefor |
| US4585830A (en) * | 1985-05-20 | 1986-04-29 | Dow Corning Corporation | Polyorganosiloxane compositions useful for preparing unsupported extruded profiles |
| JPH0816193B2 (ja) * | 1985-06-03 | 1996-02-21 | ゼロツクス コ−ポレ−シヨン | 熱安定化シリコ−ンエラストマ− |
| IL78560A0 (en) | 1985-06-28 | 1986-08-31 | Miles Lab | Electrochemical sensor and membrane therefor |
| US4659621A (en) * | 1985-08-22 | 1987-04-21 | Xerox Corporation | Release agent donor member and fusing assembly containing same |
| US4613659A (en) * | 1985-12-16 | 1986-09-23 | Dow Corning Corporation | Low temperature polymethylsiloxane containing silicon-bonded hydrogen and curable compositions made therewith |
| US4737552A (en) * | 1986-06-30 | 1988-04-12 | Dow Corning Corporation | Ceramic materials from polycarbosilanes |
| US4719275A (en) * | 1986-07-02 | 1988-01-12 | Dow Corning Corporation | Heat stable fluorinated polyorganosiloxane compositions |
| US4785066A (en) * | 1986-08-22 | 1988-11-15 | Dow Corning Corporation | Novel organosiloxane inhibitors for hydrosilation reactions |
| US4847228A (en) * | 1987-06-02 | 1989-07-11 | Toray Silicone Co., Ltd. | Platinum-alkenylsiloxane complex catalyst composition |
| US4784879A (en) * | 1987-07-20 | 1988-11-15 | Dow Corning Corporation | Method for preparing a microencapsulated compound of a platinum group metal |
| US4766176A (en) * | 1987-07-20 | 1988-08-23 | Dow Corning Corporation | Storage stable heat curable organosiloxane compositions containing microencapsulated platinum-containing catalysts |
| USRE33749E (en) * | 1987-07-20 | 1991-11-19 | Dow Corning Corporation | Storage stable heat curable organosiloxane compositions containing microencapsulated platinum-containing catalysts |
| US5026768A (en) * | 1987-12-09 | 1991-06-25 | Dow Corning Corporation | Method of producing silicone emulsion |
| US4978710A (en) * | 1987-12-09 | 1990-12-18 | Dow Corning Corporation | Method of producing silicone emulsion |
| US5026769A (en) * | 1987-12-09 | 1991-06-25 | Dow Corning Corporation | Method of producing silicone emulsion |
| US4791186A (en) * | 1988-01-04 | 1988-12-13 | Dow Corning Corporation | Method for preparing storage stable, one part curable polyorganosiloxane compositions |
| US5082706A (en) * | 1988-11-23 | 1992-01-21 | Dow Corning Corporation | Pressure sensitive adhesive/release liner laminate |
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Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1069148B (de) * | 1955-12-05 | 1959-11-19 | Dow Corning Corporation, Midland, Mich. (V. St. A.) | Verfahren zur Herstellung von Qrganosiliciuimverbindungen |
| US3159601A (en) * | 1962-07-02 | 1964-12-01 | Gen Electric | Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes |
-
0
- NL NL131800D patent/NL131800C/xx active
-
1965
- 1965-05-17 US US456516A patent/US3419593A/en not_active Expired - Lifetime
-
1966
- 1966-04-21 GB GB17550/66D patent/GB1127675A/en not_active Expired
- 1966-04-28 DE DED49976A patent/DE1262271B/de active Pending
- 1966-05-17 NL NL6606771A patent/NL6606771A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1668159A1 (de) * | 1966-12-01 | 1971-09-02 | Gen Electric | Organosiliziummaterialien und Verfahren zu ihrer Herstellung |
| EP2835403A1 (de) | 2013-08-06 | 2015-02-11 | HILTI Aktiengesellschaft | Dämmschichtbildende Zusammensetzung und deren Verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| NL131800C (de) | |
| NL6606771A (de) | 1966-11-18 |
| GB1127675A (en) | 1968-09-18 |
| US3419593A (en) | 1968-12-31 |
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