DE3015890A1 - METHOD FOR ADDITIONING VOLCANIZATION OF POLYMETHYLVINYLSILOXANE - Google Patents
METHOD FOR ADDITIONING VOLCANIZATION OF POLYMETHYLVINYLSILOXANEInfo
- Publication number
- DE3015890A1 DE3015890A1 DE19803015890 DE3015890A DE3015890A1 DE 3015890 A1 DE3015890 A1 DE 3015890A1 DE 19803015890 DE19803015890 DE 19803015890 DE 3015890 A DE3015890 A DE 3015890A DE 3015890 A1 DE3015890 A1 DE 3015890A1
- Authority
- DE
- Germany
- Prior art keywords
- dipl
- munich
- alkyl hydrogen
- polymethylvinylsiloxane
- hopf
- 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.)
- Withdrawn
Links
- -1 POLYMETHYLVINYLSILOXANE Polymers 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- 238000004073 vulcanization Methods 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 4
- 239000010948 rhodium Substances 0.000 claims description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 229920002379 silicone rubber Polymers 0.000 description 4
- 239000004945 silicone rubber Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- MBVAQOHBPXKYMF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MBVAQOHBPXKYMF-LNTINUHCSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- 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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Description
SCHIFF ν. FONER STREHL SCHOBEL-HOPF EBBINGHAUS FlNCKSHIP ν. FONER STREHL SCHOBEL-HOPF EBBINGHAUS FlNCK
, Beschreibung, Description
Bisher ist es bekannt, bei der Additionsvulkanisation von Silikonkautschuk als Katalysator Platin in Metallform, Hexachlorplatin(IV)-säure und weitere verschiedene, insbesondere Komplexverbindungen von Platin anzuwenden. Dazu gehören beispielsweise ein Komplex von Platin mit Olefinen, mit Cyclohexan, mit Styrol oder Pyridin (Pomeranceva M.G., Beljakova Z.V., Golubcov S.A. und Svarc N.S.: Polutschenye karbofunkcialnych organosilanov po reakcii prisojedinenija - NIITI Moskva, 1971; US-PS 3 723 497, 3 732 330, 3 516 946, 3 862 081). Platin und dessen Verbindungen, insbesondere Hexachlorplatin-(IV)-säure sind Katalysatoren, die zwar eine hohe Ausbeute der Produkte der Additions- bzw. Hydrosilylierungs-Reaktion bieten, welche jedoch auch Nachteile aufweisen, wie z.B. Empfindlichkeit gegen Katalysatorgifte, Erregung der Nebenreaktionen und Notwendigkeit, Inhibitoren beim Aufbewahren von Kautschukgemischen bei Raumtemperatur einzusetzen.So far it is known in the addition vulcanization of silicone rubber as catalyst platinum in metal form, hexachloroplatinic acid and to use other different, in particular complex compounds of platinum. These include, for example a complex of platinum with olefins, with cyclohexane, with styrene or pyridine (Pomeranceva M.G., Beljakova Z.V., Golubcov S.A. and Svarc N.S .: Polutschenye karbofunkcialnych organosilanov po reakcii prisojedinenija - NIITI Moskva, 1971; U.S. Patents 3,723,497, 3,732,330, 3,516,946, 3,862,081). Platinum and its compounds, especially hexachloroplatinic (IV) acid are catalysts which, although a high yield of the products of the addition or hydrosilylation reaction which, however, also have disadvantages, such as sensitivity to catalyst poisons, excitation of side reactions and the need to use inhibitors when storing rubber compounds at room temperature.
Das vorliegende erfindungsgemäße Verfahren soll die oben erwähnten Nachteile des Standes der Technik ausschalten. Der Erfindung liegt also die Aufgabe zugrunde, ein verbessertes Verfahren zur Additionsvulkanisation von Polymethylvinylsi— loxan zu schaffen.The present inventive method is intended to accomplish those mentioned above Eliminate the disadvantages of the prior art. The invention is therefore based on the object of an improved Process for the addition vulcanization of polymethylvinylsi— to create loxane.
Erfindungsgemäß wird diese Aufgabe so gelöst, daß Polymethylvinylsiloxane, enthaltend von O,2 bis IO Mol-% von CHo(CH„=CH)OSi-Gruppen, einer Einwirkung von Siliziumhydridverbindungen, wie z.B. Alkylhydrogensilanen, Alkylhydrogenpolysiloxanen oder cyclischen Alkylhydrogenpolysiloxanen mit mindestens zwei Wasserstoffatomen im Molekül in Anwesenheit von Rhodium-Triacetylacetonat als Katalysator unterworfen werden. Bevorzugte Verbindungen besitzen im Alkylrest 1 bis 6According to the invention this object is achieved in such a way that polymethylvinylsiloxanes, containing from O, 2 to IO mol% of CHo (CH "= CH) OSi groups, an action of silicon hydride compounds, such as alkyl hydrogen silanes, alkyl hydrogen polysiloxanes or cyclic alkyl hydrogen polysiloxanes with at least two hydrogen atoms in the molecule in the presence of rhodium triacetylacetonate as a catalyst. Preferred compounds have 1 to 6 in the alkyl radical
130044/0381130044/0381
C-Atome. Der Rest kann geradketticf oder verzweigt sein.C atoms. The remainder can be straight chain or branched.
Das erfindungsgemäße Verfahren garantiert eine zumindest zweimonatige Lagerfähigkeit der Kautschukgemische bei Raumtemperatur ohne Verwendung von Inhibitoren und sichert die Bildung eines guten KautschukskeLetts. Im Vergleich zu den Katalysatoren auf Platinbasis weist der erfindungsgemäße Katalysator den Vorteil auf, daß er nicht die Alterung der Vulkanisate negativ beeinflußt. Da er z.B. im Aceton, Benzol oder Toluol gut löslich ist, läßt er sich in Lösungsform in den vorerwähnten Lösungsmitteln ohne Schwierigkeiten in Silikonkautschukgemische einmischen. Die Konzentration von Rhodium(III)-Acetylacetonat im Silikonkautschukgemisch kann nach Umrechnung auf RhodiumThe method according to the invention guarantees at least a two-month period The rubber mixtures can be stored at room temperature without the use of inhibitors and ensure formation a good rubber chain. Compared to the catalysts the platinum-based catalyst of the invention has the The advantage is that it does not adversely affect the aging of the vulcanizates. Because it works well in acetone, benzene or toluene, for example is soluble, it can be in solution form in the aforementioned solvents without difficulty in silicone rubber mixtures interfere. The concentration of rhodium (III) acetylacetonate in the silicone rubber mixture can be calculated after conversion to rhodium
-3 -3-3 -3
1.10 bis 5.10 g pro 100 g Polymethylvinylsiloxan, enthaltend von O, 2 bis 10 Mol-?.', von Vinyleinheiten im Makromolekül, betragen.1.10 to 5.10 g per 100 g of polymethylvinylsiloxane, containing from 0.2 to 10 mol ?. ', of vinyl units in the macromolecule, be.
Das erfindungsgemäße Verfahren soll weiterhin anhand zweier, den Erfindungsumfang keineswegs begrenzenden Ausführungsbeispiele näher erläutert werden.The method according to the invention should also be based on two, the scope of the invention by no means limiting embodiments are explained in more detail.
Einem Silikonkautschukgomisch, bestehend aus 100 Gewichtsteilen Polymethylvinylsiloxan (Molekulargewicht. 4,6.3.0 ; Gehalt 1,4 Mol-SS ChU(CfU=CtI)OSi) und 35 GewichtsLeilen von pyrocjenem Siliciumdioxid, wurden 8,5 q Polymethylhydrocjonsiloxan (Molekulargewicht lOO; Wasserstoffgehalt O,5 bis 0,75 Gew.-%) und 5 g der Lösung von Rhodium-Triacetylacetonat in Toluol (O,11%-ige Konz.) zugegeben, worauf das Gemisch homogenisiert wurde. Das homogenisierte Gemisch wurde 30 Minuten bei 150°C vulkanisiert. Das Vulkanisat wies die nachfolgenden physiko-mechanischen Eigenschaften auf:A silicone rubber compound, consisting of 100 parts by weight Polymethylvinylsiloxane (molecular weight. 4,6.3.0; content 1.4 mol SS ChU (CfU = CtI) OSi) and 35 parts by weight of pyrocjenem Silicon dioxide, were 8.5 q polymethylhydrocionosiloxane (molecular weight lOO; Hydrogen content 0.5 to 0.75% by weight) and 5 g of the solution of rhodium triacetylacetonate in toluene (O, 11% strength Conc.) Was added, whereupon the mixture was homogenized. The homogenized mixture was vulcanized at 150 ° C. for 30 minutes. The vulcanizate exhibited the following physico-mechanical Features on:
Zugfestigkeit 4,6 MPaTensile strength 4.6 MPa
Dehnung 120 %Elongation 120%
Härte 67 ShHardness 67 Sh
1300U/03611300U / 0361
BAD ORIGINALBATH ORIGINAL
Gewichtsabnahme nach Alterung (2OO°C - 500 Stunden), 1,2 %.Weight loss after aging (200 ° C - 500 hours), 1.2%.
Polymethylvinylsiloxane mit O, 2 Mol-JS-igem, 1, 4 . Mol-%-igem und 3,5 Mol-%-igem Gehalt von Vinyleinheiten und dem Füllmittelgehalt wie im Beispiel 1 wurden in Anwesenheit von Rhodium-Acetylacetonat von gleicher Konzentration wie im Beispiel 1 und beim Verhältnis von H:Vi = 0,65 vulkanisiert. Zum Vergleich wurde die Vulkanisation dieser Polysiloxane mittels Dicumylperoxid und 2,4-Dichlorbenzoylperoxid vorgenommen.Polymethylvinylsiloxanes with O, 2 mol-JS-igem, 1, 4. Mol% and 3.5 mol% content of vinyl units and the filler content as in Example 1 were in the presence of rhodium acetylacetonate vulcanized at the same concentration as in Example 1 and at the ratio of H: Vi = 0.65. For comparison was the vulcanization of these polysiloxanes using dicumyl peroxide and 2,4-dichlorobenzoyl peroxide.
130044/0361130044/0361
ORIG/NAL"ORIG / NAL "
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803015890 DE3015890A1 (en) | 1980-04-24 | 1980-04-24 | METHOD FOR ADDITIONING VOLCANIZATION OF POLYMETHYLVINYLSILOXANE |
| FR8009865A FR2481706A1 (en) | 1980-04-24 | 1980-04-30 | Addn. vulcanisation of poly:methyl-vinyl-siloxane! - with silicon hydride using rhodium tri:acetyl-acetonate as catalyst (CS 28.11.80) |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803015890 DE3015890A1 (en) | 1980-04-24 | 1980-04-24 | METHOD FOR ADDITIONING VOLCANIZATION OF POLYMETHYLVINYLSILOXANE |
| FR8009865A FR2481706A1 (en) | 1980-04-24 | 1980-04-30 | Addn. vulcanisation of poly:methyl-vinyl-siloxane! - with silicon hydride using rhodium tri:acetyl-acetonate as catalyst (CS 28.11.80) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3015890A1 true DE3015890A1 (en) | 1981-10-29 |
Family
ID=25785122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803015890 Withdrawn DE3015890A1 (en) | 1980-04-24 | 1980-04-24 | METHOD FOR ADDITIONING VOLCANIZATION OF POLYMETHYLVINYLSILOXANE |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE3015890A1 (en) |
| FR (1) | FR2481706A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10235267A1 (en) * | 2002-08-01 | 2004-02-12 | Wacker-Chemie Gmbh | Use of rhodium-crosslinking silicone elastomers for the production of baking tins |
| DE10235268A1 (en) * | 2002-08-01 | 2004-02-12 | Wacker-Chemie Gmbh | Crosslinking silicone elastomers, processes for their production and the use of the crosslinkable compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1369989A (en) * | 1970-11-27 | 1974-10-09 | Dow Corning Ltd | Organopolysiloxane elastomers |
| GB1476314A (en) * | 1973-06-23 | 1977-06-10 | Dow Corning Ltd | Coating process |
-
1980
- 1980-04-24 DE DE19803015890 patent/DE3015890A1/en not_active Withdrawn
- 1980-04-30 FR FR8009865A patent/FR2481706A1/en not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10235267A1 (en) * | 2002-08-01 | 2004-02-12 | Wacker-Chemie Gmbh | Use of rhodium-crosslinking silicone elastomers for the production of baking tins |
| DE10235268A1 (en) * | 2002-08-01 | 2004-02-12 | Wacker-Chemie Gmbh | Crosslinking silicone elastomers, processes for their production and the use of the crosslinkable compositions |
| US7129309B2 (en) | 2002-08-01 | 2006-10-31 | Wacker-Chemie Gmbh | Use of rhodium-crosslinking silicone elastomers for producing baking molds |
| US7291670B2 (en) | 2002-08-01 | 2007-11-06 | Wacker Chemie Ag | Cross-linking silicone elastomers, method for the production thereof, and use of the cross-linkable masses |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2481706A1 (en) | 1981-11-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: VON FUENER, A., DIPL.-CHEM. DR.RER.NAT. EBBINGHAUS |
|
| 8139 | Disposal/non-payment of the annual fee |