DE1120690B - Compounds based on organopolysiloxanes that harden at room temperature when exposed to atmospheric moisture - Google Patents

Compounds based on organopolysiloxanes that harden at room temperature when exposed to atmospheric moisture

Info

Publication number
DE1120690B
DE1120690B DEW25077A DEW0025077A DE1120690B DE 1120690 B DE1120690 B DE 1120690B DE W25077 A DEW25077 A DE W25077A DE W0025077 A DEW0025077 A DE W0025077A DE 1120690 B DE1120690 B DE 1120690B
Authority
DE
Germany
Prior art keywords
harden
room temperature
aminosilanes
organopolysiloxanes
exposed
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
Application number
DEW25077A
Other languages
German (de)
Inventor
Dr Siegfried Nitzsche
Dr Manfred Wick
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wacker Chemie AG
Original Assignee
Wacker Chemie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Wacker Chemie AG filed Critical Wacker Chemie AG
Priority to DEW25077A priority Critical patent/DE1120690B/en
Priority to GB5363/60A priority patent/GB905364A/en
Priority to FR818774A priority patent/FR1248826A/en
Publication of DE1120690B publication Critical patent/DE1120690B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
    • C01F7/00—Compounds of aluminium
    • C01F7/02—Aluminium oxide; Aluminium hydroxide; Aluminates
    • C01F7/44—Dehydration of aluminium oxide or hydroxide, i.e. all conversions of one form into another involving a loss of water
    • C01F7/441—Dehydration of aluminium oxide or hydroxide, i.e. all conversions of one form into another involving a loss of water by calcination
    • 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
    • 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
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy 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
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing 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
    • C08G77/70—Siloxanes defined by use of the MDTQ nomenclature

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Geology (AREA)
  • Inorganic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Silicon Polymers (AREA)

Description

Bei Zutritt von Luftfeuchtigkeit bei Raumtemperatur härtende Massen auf Basis von Organopolysiloxanen Bei Zutritt von Feuchtigkeit härtende Organopolysiloxanmassen können nach der französischen Patentschrift 1 235 156 unter Mitverwendung der üblichen Vernetzer und Vernetzungskatalysatoren für hydroxylendblockiertes Diorganopolysiloxan dadurch hergestellt werden, daß Vernetzer und/oder Katalysator durch Aufsaugen in Molekularsiebe temporär unwirksam gemacht und erst nach Zusatz von Luftfeuchtigkeit frei werden. Diese in Gegenwart von Feuchtigkeit härtenden Massen haben den Vorteil, daß bei der Härtung keine Säure abgespalten wird, daß sie also ohne weiteres auch für elektrische Isolationszwecke eingesetzt werden können. Ihr Einsatz ist jedoch dadurch begrenzt, daß nur chemisch inerte Füllstoffe, wie Quarzmehl und Kieselgur, mitbenutzt werden können. Compounds that harden at room temperature when exposed to atmospheric moisture based on organopolysiloxanes Organopolysiloxane compounds that harden on exposure to moisture can according to French patent 1,235,156 using the usual Crosslinkers and crosslinking catalysts for hydroxyl endblocked diorganopolysiloxane be prepared in that crosslinker and / or catalyst by soaking in Molecular sieves temporarily rendered ineffective and only after the addition of humidity get free. These masses, which harden in the presence of moisture, have the advantage of that no acid is split off during the hardening process, that is to say, that they do so without further ado can be used for electrical insulation purposes. Your use is however limited by the fact that only chemically inert fillers, such as quartz powder and kieselguhr, can also be used.

Nach einem noch unveröffentlichten Vorschlag können lufthärtende Organopolysiloxanmassen mittels acyloxy - endblockierten Dialkylpolysiloxanen hergestellt werden, die an jedem Kettenende mindestens zwei Acyloxygruppen tragen müssen. Diese Acyloxyhärter haben aber den Nachteil, daß sie die Organopolysiloxane depolymerisieren, ferner spalten sie beim Härten Säure ab, demzufolge wirken sie auf Metalle korrodierend und sind somit für elektrische Zwecke nicht brauchbar. Schließlich können bei diesen Massen keine basischen Füllstoffe mitverwendet werden. Es war daher erwünscht, unter dem Einfluß der Luftfeuchtigkeit zu elastomeren Produkten härtbare Organopolysiloxanmassen zu finden, die einfach zusammengesetzt sind, jedoch bei der Härtung keine Säure abspalten. According to an as yet unpublished proposal, air-hardening Organopolysiloxane compositions produced using acyloxy end-blocked dialkylpolysiloxanes which must carry at least two acyloxy groups at each end of the chain. These Acyloxy hardeners have the disadvantage that they depolymerize the organopolysiloxanes, They also split off acid during hardening, and consequently have a corrosive effect on metals and are therefore not useful for electrical purposes. After all, you can use these Masses no basic fillers are used. It was therefore desirable under Organopolysiloxane compositions curable under the influence of atmospheric humidity to form elastomeric products to find that are simply composed, but no acid when hardening split off.

Überraschenderweise wurde gefunden, daß man dieses Ziel erreichen kann, wenn man die hydroxyl- endblockierten Organosiloxanpolymeren nicht mit acyloxylierten mehrfunktionellen Siliciumverbindungen, sondern erfindungsgemäß mit mehrfunktionellen Aminosilanen als Vernetzer versetzt. Die Aminosilane sind von der allgemeinen Formel Rn - Si(NR'R")rn worin R = Alkyl, Aryl, Aralkyl, NH oder NR'R", R' = H, Alkyl, Aryl oder Aralkyl und R" Alkyl, Aryl oder Aralkyl ist. Surprisingly, it has been found that this goal can be achieved can, if you use the hydroxyl end-blocked organosiloxane polymers not with acyloxylated ones multifunctional silicon compounds, but according to the invention with multifunctional ones Aminosilanes added as crosslinkers. The aminosilanes are of general formula Rn - Si (NR'R ") rn where R = alkyl, aryl, aralkyl, NH or NR'R", R '= H, alkyl, aryl or aralkyl and R "is alkyl, aryl, or aralkyl.

Voraussetzung für den Erfolg ist, daß mehr als zwei Si-N-Bindungen je Molekel des Vernetzers vorliegen. Es können allerdings auch Aminosilazane der allgemeinen Formel verwendet werden; diese wirken jedoch langsamer, besonders bei höherem n, und sind schwieriger herzustellen als die monomeren Aminosilane.The prerequisite for success is that there are more than two Si-N bonds per molecule of the crosslinker. However, aminosilazanes of the general formula can also be used be used; however, these act more slowly, especially at higher n, and are more difficult to produce than the monomeric aminosilanes.

Die erfindungsgemäß verwendbaren Aminosilane sind Umsetzungsprodukte von Chlorsilanen, H-Silanen oder Alkoxysilanen mit geeigneten primären und sekundären Aminen. Geeignete Chlorsilane bzw. The aminosilanes which can be used according to the invention are reaction products of chlorosilanes, H-silanes or alkoxysilanes with suitable primary and secondary Amines. Suitable chlorosilanes or

Alkoxysilane zur Herstellung solcher Silane sind z. B. Tetrachlorsilan, Tetraäthoxysilan, Methyltri- chlorsilan, Methyltripropoxysilan, Phenyltrimethoxysilan, Phenyltrichlorsilan und Phenylsilan.Alkoxysilanes for the production of such silanes are z. B. Tetrachlorosilane, Tetraethoxysilane, methyltri- chlorosilane, methyltripropoxysilane, phenyltrimethoxysilane, Phenyltrichlorosilane and phenylsilane.

Die Aminosilane sollen mehr als difunktionell sein, da sonst keine Vernetzung eintritt; vorzugsweise sind sie tri- oder tetrafunktionell. Je höher die Funktionalität der verwendeten Silane ist, desto schneller tritt die Härtung bei Zutritt von Feuchtigkeit ein. Es wurde außerdem gefunden, daß unsubstituierte oder alkylsubstituierte Silane eine schnellere Härtung bei Zutritt von Feuchtigkeit bewirken als arylsubstituierte Silane. In all den Fällen, wo besonders schnell gehärtet werden soll, verwendet man also unsubstituierte Silane oder alkylsubstituierte Silane. Soll die Härtung langsamer erfolgen, so bevorzugt man arylsubstituierte Aminosilane. The aminosilanes should be more than bifunctional, otherwise none Networking occurs; they are preferably tri- or tetrafunctional. The higher the functionality of the silanes used, the faster the curing occurs in the presence of moisture. It was also found that unsubstituted or alkyl-substituted silanes a faster cure upon entry from moisture act as aryl-substituted silanes. In all those cases where special is to be cured quickly, one uses unsubstituted silanes or alkyl-substituted ones Silanes. If curing is to take place more slowly, preference is given to aryl-substituted ones Aminosilanes.

Geeignete Amine zur Herstellung der erfindungsgemäß verwendeten Aminosilane sind aliphatische und aromatische bzw. araliphatische primäre und sekundäre Amine bzw. Ammoniak; solche Amine sind z. B. Monobutylamin, Diäthylamin, Anilin und Methylanilin. Suitable amines for the preparation of the aminosilanes used according to the invention are aliphatic and aromatic or araliphatic primary and secondary amines or ammonia; such amines are e.g. B. monobutylamine, diethylamine, aniline and methylaniline.

Die Vernetzung unter dem Einfluß der Luftfeuchtigkeit erfolgt vermutlich einfach dadurch, daß die Aminosilane beim Zutritt von Luftfeuchtigkeit in Silanole und Amine gespalten werden, wobei das entstehende mehr als difunktionelle Silanol als Vernetzer und das Amin als Vernetzungskatalysator wirkt. The crosslinking presumably takes place under the influence of air humidity simply because the aminosilanes turn into silanols when exposed to humidity and amines are cleaved, the resulting more than difunctional silanol acts as a crosslinker and the amine acts as a crosslinking catalyst.

In Übereinstimmung mit dieser Annahme ist es auch nicht notwendig, hydroxyl-endblockierte Diorganosiloxane, die als Ausgangsstoff zur Herstellung der in Gegenwart von Feuchtigkeit zu Elastomeren härtenden Massen dienen, vorher mit den Aminosilanen zur Reaktion zu bringen, sondern es genügt einfach, diese Silane der mit Füllstoff versehenen Organopolysiloxanmischung als Härter zuzusetzen. In accordance with this assumption, it is also not necessary hydroxyl-endblocked diorganosiloxanes, which are used as starting material for the production of serve in the presence of moisture to form elastomers hardening masses, beforehand with the aminosilanes to react, but it is enough simply to use these silanes to be added to the organopolysiloxane mixture provided with filler as a hardener.

Die erfindungsgemäß verwendeten Vernetzungsmittel zeigen den Vorteil, daß sie die Organopolysiloxane in Lösung nicht depolymerisieren. Ein weiterer Vorteil bei der Erfindung ist die Tatsache, daß jeder Füllstoff eingesetzt werden kann, d. h., außer inerten können auch basische Füllstoffe, wie z. B. Zinkcarbonat, Zinkoxyd, Calciumoxyd, Calciumcarbonat, Magnesiumoxyd und Magnesiumcarbonat, verwendet werden; da diese basischen Füllstoffe als Beschleuniger wirken, tritt beim Auftragen dicker Schichten eine schnellere Durchhärtung ein. Selbst Säurefüllstoffe, wie auf dem Flammenweg hergestellte Kieselsäuren, beeinträchtigen die Härterwirkung der Aminosilane nicht. The crosslinking agents used according to the invention have the advantage that they do not depolymerize the organopolysiloxanes in solution. Another advantage in the invention is the fact that any filler can be used d. That is, in addition to inert, basic fillers, such as e.g. B. zinc carbonate, zinc oxide, Calcium oxide, calcium carbonate, magnesium oxide and magnesium carbonate can be used; Since these basic fillers act as accelerators, it occurs thicker when applied Layers in for faster curing. Even acid fillers, like on that Silicas produced by flame, impair the hardening effect of the aminosilanes not.

Die erfindungsgemäß mit Hilfe der Aminosilane zu vernetzenden linearen Diorganopolysiloxane können die üblichen in der Organopolysiloxantechnik verwendeten Organogruppen tragen. Hinsichtlich des Molekulargewichtes besteht weder nach oben noch nach unten eine Beschränkung. Da bekanntlich die mechanischen Eigenschaften der Härtungsprodukte um so schlechter werden, je niedriger das Molekulargewicht der verwendeten Diorganopolysiloxane ist, wird man in der Praxis hauptsächlich Diorganopolysiloxane mit einem Polymerisationsgrad über 50 einsetzen. Ein Polymerisationsgrad von 10 000 ist üblicherweise der höchste, der bei handelsüblichen Diorganopolysiloxanen erreicht werden kann. The linear ones to be crosslinked according to the invention with the aid of the aminosilanes Diorganopolysiloxanes can be those customarily used in organopolysiloxane technology Carry organogroups. With regard to the molecular weight, there is no upward trend one more limit downwards. As is well known, the mechanical properties the lower the molecular weight, the worse the hardening products become of the diorganopolysiloxanes used, in practice one will mainly use diorganopolysiloxanes use with a degree of polymerization above 50. A degree of polymerization of 10 000 is usually the highest for commercial diorganopolysiloxanes can be reached.

An die linearen Diorganopolysiloxane ist lediglich die Forderung zu stellen, daß sie reaktionsfähige Endgruppen haben müssen. Solche reaktionsfähige Endgruppen können sein: Hydroxylgruppen, Alkoxyl-bzw. Aroxylgruppen, Acyloxygruppen oder an Silicium gebundener Wasserstoff. Vorzugsweise werden hydroxyl-endblockierte Diorganopolysiloxane ververwendet, da diese am leichtesten herzustellen sind. There is only one requirement for the linear diorganopolysiloxanes to ask that they must have reactive end groups. Such responsive End groups can be: hydroxyl groups, alkoxyl or. Aroxyl groups, acyloxy groups or hydrogen bonded to silicon. Preference is given to hydroxyl end-blocked Diorganopolysiloxanes are used because these are the easiest to make.

Die notwendigen Mengen an Aminosilanen sind gering; sie hängen praktisch ausschließlich vom Molekulargewicht des Organosiloxanpolymeren ab. The necessary amounts of aminosilanes are small; they practically hang solely on the molecular weight of the organosiloxane polymer.

Es sollte so viel Silan zugesetzt werden, daß pro Mol reaktionsfähiger Endgruppe 1 Mol Silan zugegen ist.Sufficient silane should be added to make it more reactive per mole End group 1 mole of silane is present.

In der Praxis kommt man mit Zusatzmengen zwischen 0,05 und 1°/o aus; diese Zahlenangabe soll jedoch keine Begrenzung nach oben darstellen, da selbstverständlich auch ein Überschuß verwendet werden kann.In practice it is possible to use additional amounts between 0.05 and 1%; However, this figure is not intended to represent an upper limit, as it goes without saying an excess can also be used.

Die Mischungen aus Diorganopolysiloxan mit reaktionsfähigen Endgruppen und gegebenenfalls Füllstoffen sowie mehr als difunktionellem Aminosilan oder Organoaminosilan härten bereits bei Zutritt von Feuchtigkeit. Die Härtungsgeschwindigkeit ist abhängig vom Grad der Luftfeuchtigkeit, von der Schichtdicke, vom Molekulargewicht des verwendeten Polymeren, von der Funktionalität des Aminosilans, von den organischen Gruppen, die am Siliciumatom des Silans sitzen, und schließlich auch von der Aminkomponente im Silan. Je höher die Luftfeuchtigkeit, desto schneller erfolgt die Härtung; je größer das Molekulargewicht des Polymeren ist, desto schneller erfolgt die Härtung; je höher die Funktionalität des Silans und je kleiner der an Silicium gebundene organische Rest im Silan ist, desto schneller härtet die Masse durch, und schließlich erfolgt die Härtung schneller bei der Verwendung primärer Amine als Silankompomente bzw. bei der Verwendung aliphatischer siliciumhaltiger Amine. Sekundäre Amine und aromatische Amine zeigen, wenn sie als Silankomponente verwendet werden, eine wesentlich kleinere Härtungsgeschwindigkeit. The mixtures of diorganopolysiloxane with reactive end groups and optionally fillers and more than difunctional aminosilane or organoaminosilane harden even when moisture is exposed. The curing speed is dependent the degree of humidity, the layer thickness, the molecular weight of the used Polymers, the functionality of the aminosilane, the organic groups, which sit on the silicon atom of the silane, and finally also on the amine component in the silane. The higher the humidity, the faster the hardening takes place; ever the greater the molecular weight of the polymer, the faster the curing takes place; the higher the functionality of the silane and the smaller the silicon bonded If there is an organic residue in the silane, the faster the mass hardens, and finally the curing takes place faster when using primary amines as silane components or when using aliphatic silicon-containing amines. Secondary amines and aromatic amines, when used as the silane component, exhibit an essential feature slower curing speed.

Die unter erfindungsgemäßer Verwendung von Aminosilanen oder Silazanen hergestellten Massen sind beispielsweise anwendbar als hitze-, kälte- und ozonfeste Dichtungsmaterialien, Fugendichtungsmaterial, zahnärztliche Verschlußmassen, Elektroisolierungen, Kleber für Organopolysiloxanfolien und -formteile, Organopolysiloxananstrichlacke sowie Gewebe- und Papierimprägnierlacke. Those using aminosilanes or silazanes according to the invention The masses produced can be used, for example, as heat, cold and ozone resistant Sealing materials, joint sealing material, dental sealing compounds, electrical insulation, Adhesives for organopolysiloxane films and moldings, organopolysiloxane paints as well as fabric and paper impregnation varnishes.

Beispiel 1 Einem hydroxyl-endblockierten Dimethylpolysiloxan mit einer Viskosität von 10 500 cSt werden erfindungsgemäß 0,5 0/o Methyltri-N,N-dibutylsil an zugesetzt. Example 1 A hydroxyl-endblocked dimethylpolysiloxane with a viscosity of 10,500 cSt is 0.5 0 / o methyltri-N, N-dibutylsil according to the invention added on.

Wird diese Masse anschließend in 3 mm dicker Schicht in eine Glasschale gegossen, so härtet sie bei einer relativen Luftfeuchtigkeit von 65 01o innerhalb von 4 Stunden vollständig bei Raumtemperatur aus. This mass is then placed in a 3 mm thick layer in a glass bowl poured, it hardens within a relative humidity of 65 01o of 4 hours completely at room temperature.

Beispiel 2 100 g eines Dimethylpolysiloxans mit Äthoxylendgruppen und einer Viskosität von 23 400 cSt werden mit 50 g Calciumcarbonat und erfindungsgemäß 0,4 g Phenyltri-N-äthylsilan versetzt. Example 2 100 g of a dimethylpolysiloxane with ethoxyl end groups and a viscosity of 23 400 cSt are with 50 g calcium carbonate and according to the invention 0.4 g of phenyltri-N-ethylsilane are added.

Wird diese Masse in 3 mm dicker Schicht auf Holz aufgespachtelt, so härtet sie bei einer Luftfeuchtigkeit von 6501o innerhalb von 4 Stunden durch. If this compound is applied to wood in a 3 mm thick layer, it hardens within 4 hours at a humidity of 6501o.

Beispiel 3 100 g eines Si-H-endblockierten Organopolysiloxans der Formel werden mit 100 g Quarzmehl und erfindungsgemäß 0,5 g Monomethyltri-N-butylsilan vermischt.Example 3 100 g of an Si-H end-blocked organopolysiloxane of the formula are mixed with 100 g of quartz powder and, according to the invention, 0.5 g of monomethyltri-N-butylsilane.

Füllt man mit dieser Masse eine Zahnkavität von 3 mm Tiefe, so erhärtet die Masse im Munde innerhalb von 30 Minuten und bildet einen hervorragenden Abschluß dieser Kavität. If a tooth cavity 3 mm deep is filled with this mass, it hardens the mass in the mouth within of 30 minutes and forms an excellent Completion of this cavity.

Claims (1)

PATENTANSPRUCH: Bei Zutritt von Luftfeuchtigkeit bei Raumtemperatur härtende Massen auf Basis von hydroxyl- endblockierten Diorganopolysiloxanen, Vernetzungsmitteln und Füllstoffen, enthaltend geringe Mengen mehrfunktioneller Aminosilane der allgemeinen Formel Rn-Si (NR'R")m oder Aminosilazane der allgemeinen Formel (R' R" N)2 Si(R)[N HSi(R) NR' R"]nNHSi(R) (NR' R")2 (R = Alkyl, Aryl, Aralkyl, NH2 oder NR'R", R' = H, Alkyl, Aryl oder Aralkyl, R"= H, Alkyl, Aryl oder Aralkyl). PATENT CLAIM: In the presence of humidity at room temperature hardening compounds based on hydroxyl end-blocked diorganopolysiloxanes, crosslinking agents and fillers containing small amounts of multifunctional aminosilanes of the general Formula Rn-Si (NR'R ") m or aminosilazanes of the general formula (R 'R" N) 2 Si (R) [N HSi (R) NR 'R "] nNHSi (R) (NR' R") 2 (R = alkyl, aryl, aralkyl, NH2 or NR'R ", R '= H, alkyl, aryl or aralkyl, R ″ = H, alkyl, aryl or aralkyl). In Betracht gezogene Druckschriften: Deutsche Patentschriften Nr. 949 604, 1 003 441; deutsche Auslegeschrift Nr. 1 027 826. Considered publications: German Patent Specifications No. 949 604, 1 003 441; German interpretative document No. 1 027 826.
DEW25077A 1959-02-20 1959-02-20 Compounds based on organopolysiloxanes that harden at room temperature when exposed to atmospheric moisture Pending DE1120690B (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DEW25077A DE1120690B (en) 1959-02-20 1959-02-20 Compounds based on organopolysiloxanes that harden at room temperature when exposed to atmospheric moisture
GB5363/60A GB905364A (en) 1959-02-20 1960-02-15 Silicone compositions
FR818774A FR1248826A (en) 1959-02-20 1960-02-17 Air-curing silicone rubber masses

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEW25077A DE1120690B (en) 1959-02-20 1959-02-20 Compounds based on organopolysiloxanes that harden at room temperature when exposed to atmospheric moisture

Publications (1)

Publication Number Publication Date
DE1120690B true DE1120690B (en) 1961-12-28

Family

ID=7598006

Family Applications (1)

Application Number Title Priority Date Filing Date
DEW25077A Pending DE1120690B (en) 1959-02-20 1959-02-20 Compounds based on organopolysiloxanes that harden at room temperature when exposed to atmospheric moisture

Country Status (3)

Country Link
DE (1) DE1120690B (en)
FR (1) FR1248826A (en)
GB (1) GB905364A (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1191571B (en) * 1962-06-28 1965-04-22 Midland Silicones Ltd Organopolysiloxane molding compositions which can be stored in the absence of water and hardenable to elastomers in the presence of the same
DE1224039B (en) * 1964-02-06 1966-09-01 Bayer Ag Plastic organopolysiloxane molding compounds which can be stored under exclusion of water
DE1240664B (en) * 1963-12-20 1967-05-18 Gen Electric Process for the preparation of organopolysiloxane elastomers
DE1255924B (en) * 1966-02-11 1967-12-07 Wacker Chemie Gmbh Organopolysiloxane molding compounds which harden at room temperature with the ingress of water to form elastomers
DE1260140B (en) * 1966-02-11 1968-02-01 Wacker Chemie Gmbh Organopolysiloxane molding compounds which can be stored under exclusion of water and harden at room temperature to give elastomers
DE1264058B (en) * 1965-01-04 1968-03-21 Gen Electric Silicone molding compound that can be stored in the absence of moisture and hardenable to form elastomers in the presence of the same
DE1298278B (en) * 1965-05-03 1969-06-26 Gen Electric Molding compound, which can be converted into the hardened, solid and elastic state by the ingress of moisture and which can be stored in the absence of moisture, on the basis of silanol end-blocked polydiorganosiloxane
DE1963571A1 (en) * 1968-12-20 1970-10-29 Midland Siliconas Ltd Process for crosslinking polyolefins
DE1719315B1 (en) * 1966-09-26 1972-04-27 Wacker Chemie Gmbh CROSS-LINKING AGENTS FOR THE PRODUCTION OF ORGANOPOLYSILOXANE MATERIALS THAT HARD TO ELASTOMER AT ROOM TEMPERATURE
DE2244644A1 (en) * 1971-09-13 1973-03-22 Gen Electric SELF-ADHESIVE TWO-COMPONENT SILICONE RUBBER COMPOSITIONS VULCANIZABLE AT ROOM TEMPERATURE
EP0384183A2 (en) * 1982-02-17 1990-08-29 General Electric Company Mixtures comprising silanol-terminated polydiorganosiloxane and processes
US12018151B2 (en) 2020-03-09 2024-06-25 Wolfgang Hechtl Preparation for producing a polymer crosslinkable by condensation reaction, polymer composition crosslinkable by condensation reaction, process for producing a silicone elastomer and silicone elastomer

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3305525A (en) * 1967-02-21 Method for making organosilicon polymers
US3133110A (en) * 1961-04-05 1964-05-12 Union Carbide Corp Reaction of silylamines with hydroxy-silicon compounds
US4267297A (en) * 1979-10-19 1981-05-12 Toray Silicone Company, Ltd. Room temperature curable silicone resins
GB8401016D0 (en) * 1984-01-14 1984-02-15 Hagen Perennatorwerk Organopolysiloxane compositions
FR2642765B1 (en) * 1989-02-03 1991-04-26 Rhone Poulenc Chimie AQUEOUS SILICONE DISPERSION BASED ON AMINOSILANE AND / OR AMIDOSILANE CROSSLINKING TO AN ELASTOMER BY REMOVAL OF WATER
US8557761B2 (en) * 2007-03-16 2013-10-15 Kathryn L. Keyt Infused sealant system
KR20100087227A (en) 2007-12-20 2010-08-03 블루스타 실리콘즈 프랑스 에스에이에스 Room-temperature vulcanisable organopolysiloxane compound to give an elastomer and novel organopolysiloxane polycondensation catalysts
FR2946657A1 (en) 2009-06-12 2010-12-17 Bluestar Silicones France METHOD FOR SEALING AND ASSEMBLING COMPONENTS OF A MOTOR-PROPELLER GROUP
FR2946656A1 (en) 2009-06-12 2010-12-17 Bluestar Silicones France METHOD FOR SEALING AND ASSEMBLING COMPONENTS OF A MOTOR-PROPELLER GROUP
FR2946655A1 (en) 2009-06-15 2010-12-17 Bluestar Silicones France PROCESS FOR COATING A SILICONE COMPOSITION CONTAINING NO TIN ON A FLEXIBLE SUPPORT
FR2946654A1 (en) 2009-06-15 2010-12-17 Bluestar Silicones France PROCESS FOR COATING A SILICONE COMPOSITION CONTAINING NO TIN ON A FLEXIBLE SUPPORT
ES2602740T3 (en) 2010-03-16 2017-02-22 Bluestar Silicones France Procedure and compositions useful for sealing and assembling components of a motor-propeller group
US9157009B2 (en) 2011-07-07 2015-10-13 Bluestar Silicones France Sas Uses of carbenes in solution as organopolysiloxane polycondensation catalysts
EP2756211B1 (en) 2011-09-16 2019-04-24 ELKEM SILICONES France SAS Method and composition for sealing and assembling components of a power train
CN104981524B (en) 2012-12-20 2020-03-13 埃肯有机硅法国简易股份公司 Organopolysiloxane compositions vulcanizable at ambient temperature into elastomers and novel organopolysiloxane polycondensation catalysts
CN104981523B (en) 2012-12-20 2018-10-09 埃肯有机硅法国简易股份公司 The organopolysiloxane composition and organopolysiloxane polycondensation catalysts of elastomer-forming can be vulcanized at ambient temperature
EP2935492B1 (en) 2012-12-20 2016-10-26 Bluestar Silicones France SAS Article with antifouling properties, intended for aquatic uses and, in particular, for marine uses
FR2999980A1 (en) 2012-12-20 2014-06-27 Bluestar Silicones France ARTICLE HAVING ANTIFOULING PROPERTIES AND INTENDED FOR USE IN AQUATIC APPLICATIONS, IN PARTICULAR MARINE
FR3000090A1 (en) 2012-12-20 2014-06-27 Bluestar Silicones France METHOD AND COMPOSITIONS USEFUL FOR SEALING AND ASSEMBLING COMPONENTS OF A MOTOR-PROPELLER GROUP
FR3014107A1 (en) 2013-12-03 2015-06-05 Bluestar Silicones France ARTICLE HAVING ANTIFOULING PROPERTIES AND INTENDED FOR USE IN AQUATIC APPLICATIONS, IN PARTICULAR MARINE
FR3014106B1 (en) 2013-12-03 2017-03-10 Bluestar Silicones France CURABLE SILICONE COMPOSITION IN THE PRESENCE OF WATER OR HUMIDITY IN THE AIR
KR102373923B1 (en) 2017-06-29 2022-03-11 엘켐 실리콘즈 프랑스 에스에이에스 Method of manufacturing silicone elastomer mold

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE949604C (en) * 1952-12-03 1956-09-20 Dow Corning Process for the production of siloxane elastomers
DE1027826B (en) * 1957-01-19 1958-04-10 Bayer Ag Silicone adhesive

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE949604C (en) * 1952-12-03 1956-09-20 Dow Corning Process for the production of siloxane elastomers
DE1027826B (en) * 1957-01-19 1958-04-10 Bayer Ag Silicone adhesive

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1191571B (en) * 1962-06-28 1965-04-22 Midland Silicones Ltd Organopolysiloxane molding compositions which can be stored in the absence of water and hardenable to elastomers in the presence of the same
DE1240664B (en) * 1963-12-20 1967-05-18 Gen Electric Process for the preparation of organopolysiloxane elastomers
DE1224039B (en) * 1964-02-06 1966-09-01 Bayer Ag Plastic organopolysiloxane molding compounds which can be stored under exclusion of water
DE1264058B (en) * 1965-01-04 1968-03-21 Gen Electric Silicone molding compound that can be stored in the absence of moisture and hardenable to form elastomers in the presence of the same
DE1298278B (en) * 1965-05-03 1969-06-26 Gen Electric Molding compound, which can be converted into the hardened, solid and elastic state by the ingress of moisture and which can be stored in the absence of moisture, on the basis of silanol end-blocked polydiorganosiloxane
US3408325A (en) * 1966-02-11 1968-10-29 Wacker Chemie Gmbh Room temperature vulcanizable organopolysiloxane elastomers
DE1260140B (en) * 1966-02-11 1968-02-01 Wacker Chemie Gmbh Organopolysiloxane molding compounds which can be stored under exclusion of water and harden at room temperature to give elastomers
DE1255924B (en) * 1966-02-11 1967-12-07 Wacker Chemie Gmbh Organopolysiloxane molding compounds which harden at room temperature with the ingress of water to form elastomers
US3464951A (en) * 1966-02-11 1969-09-02 Wacker Chemie Gmbh Room temperature vulcanizing silicone rubber stock
DE1719315B1 (en) * 1966-09-26 1972-04-27 Wacker Chemie Gmbh CROSS-LINKING AGENTS FOR THE PRODUCTION OF ORGANOPOLYSILOXANE MATERIALS THAT HARD TO ELASTOMER AT ROOM TEMPERATURE
DE1963571A1 (en) * 1968-12-20 1970-10-29 Midland Siliconas Ltd Process for crosslinking polyolefins
DE2244644A1 (en) * 1971-09-13 1973-03-22 Gen Electric SELF-ADHESIVE TWO-COMPONENT SILICONE RUBBER COMPOSITIONS VULCANIZABLE AT ROOM TEMPERATURE
EP0384183A2 (en) * 1982-02-17 1990-08-29 General Electric Company Mixtures comprising silanol-terminated polydiorganosiloxane and processes
EP0384183A3 (en) * 1982-02-17 1991-06-05 General Electric Company Mixtures comprising silanol-terminated polydiorganosiloxane and processes
US12018151B2 (en) 2020-03-09 2024-06-25 Wolfgang Hechtl Preparation for producing a polymer crosslinkable by condensation reaction, polymer composition crosslinkable by condensation reaction, process for producing a silicone elastomer and silicone elastomer

Also Published As

Publication number Publication date
FR1248826A (en) 1960-12-23
GB905364A (en) 1962-09-05

Similar Documents

Publication Publication Date Title
DE1120690B (en) Compounds based on organopolysiloxanes that harden at room temperature when exposed to atmospheric moisture
EP2176351B1 (en) Cross-linkable masses based on organosilicon compounds
JP3927950B2 (en) Organopolysiloxane composition, process for its production, crosslinkable material produced from said composition, and molded article produced from said material
EP2855591B1 (en) Crosslinkable compositions based on organosilicon compounds
DE19616789A1 (en) Adhesive RTV silicone rubber compounds
DE1244403B (en) Organopolysiloxane molding compounds that can be stored in the absence of water
DE68923658T2 (en) Polysiloxane composition curable at ambient temperature.
EP3215570B1 (en) Crosslinkable organopolysiloxane compositions
DE2754703C3 (en) Process for the preparation of mercaptoorganopolysiloxane elastomers
EP2176352B1 (en) Cross-linkable masses based on organosilicon compounds
EP0885915A2 (en) Polyorganosiloxanes having dialkoxyorganosiloxy groups
DE10319303A1 (en) Process for the preparation of crosslinkable compositions based on organosilicon compounds
EP0415596B1 (en) Silicone sealants
DE1255924B (en) Organopolysiloxane molding compounds which harden at room temperature with the ingress of water to form elastomers
EP1853659B1 (en) Cross-linkable masses based on organosilicon compounds
DE102005060649A1 (en) Crosslinkable compositions based on organosilicon compounds
EP3735447A1 (en) Silicone sealant having adjustable flow properties
WO1999032551A1 (en) Organopolysiloxane materials which can be cross-linked by cleaving alcohols into elastomers
EP0582610B1 (en) Organo(poly)siloxanes, their production and use
DE1745498B2 (en) AFTER THE ACCESS OF MOISTURE AT ROOM TEMPERATURE, MIXTURES OF LINEAR ORGANOPOLYSILOXAMINES AND ORGANOSILICON COMPOUNDS HAVE TO BE ELASTOMERED
JP3457075B2 (en) Method for producing one-part room temperature curable silicone elastomer composition
DE102007037196A1 (en) Cross linkable mass, obtained by condensation reaction using organosilicon compounds (II)containing units and physical propellants, useful e.g. to prepare molded article and for the insulation of electric or electronic devices
EP0948501A1 (en) Organosilicon compounds having urea groups, method for producing same and their utilization
DE1769537C3 (en) Organopolysiloxane molding compounds which can be stored in the absence of water and which cure in the presence of water to give elastomeric solids
WO2023186261A1 (en) Cross-linkable compositions on the basis of organosilicon compounds