DE1193504B - Process for the preparation of polysiloxanes with terminal diketone groups - Google Patents
Process for the preparation of polysiloxanes with terminal diketone groupsInfo
- Publication number
- DE1193504B DE1193504B DEB76502A DEB0076502A DE1193504B DE 1193504 B DE1193504 B DE 1193504B DE B76502 A DEB76502 A DE B76502A DE B0076502 A DEB0076502 A DE B0076502A DE 1193504 B DE1193504 B DE 1193504B
- Authority
- DE
- Germany
- Prior art keywords
- polysiloxanes
- diketone
- preparation
- terminal
- groups
- 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
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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0876—Reactions involving the formation of bonds to a Si atom of a Si-O-Si sequence other than a bond of the Si-O-Si linkage
- C07F7/0878—Si-C bond
- C07F7/0879—Hydrosilylation reactions
-
- 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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
Description
Verfahren zur Herstellung von Polysiloxanen mit endständigen Diketongruppen Ziel der Erfindung ist ein Verfahren zur Herstellung von niedermolekularen Polysiloxanen, deren Endgruppen durch 8-Diketongruppen substituiert sind. Solche Verbindungen, die durch die allgemeine Formel Diketon Diketon wiedergegeben werden können, waren bisher nicht bekannt.Process for the preparation of polysiloxanes with terminal diketone groups The aim of the invention is a process for the preparation of low molecular weight polysiloxanes, the end groups of which are substituted by 8-diketone groups. Such compounds represented by the general formula diketone Diketone can be reproduced, were previously unknown.
Einfache Organosilyl-ß-diketone sind beständig, wenn der Silylrest von einer Ketongruppe durch mindestens 2 Kohlenstoffatome getrennt ist. Solche wurden hergestellt durch Umsetzung von ,8-Silylketonen mit Carbonsäureestern oder Ketonen nach Art einer Claisenkondensation; (vgl. S o mmer, P i 0 c h, J. Amer. chem. Soc., 76, S. 1606 [1954], sowie USA.-Patentschrift 2 634 282). Diese Methode läßt sich jedoch nicht auf die Herstellung von Polysiloxanen mit Diketonendgruppen übertragen, da hierbei Spaltung von Siloxanbindungen eintritt. Simple organosilyl-ß-diketones are stable if the silyl radical is separated from a ketone group by at least 2 carbon atoms. Such were produced by reacting, 8-silyl ketones with carboxylic acid esters or ketones in the manner of a Claisen condensation; (cf. S o mmer, P i 0 c h, J. Amer. chem. Soc., 76, p. 1606 [1954], as well as U.S. Patent 2,634,282). This method can be but not transferred to the production of polysiloxanes with diketone end groups, since this causes cleavage of siloxane bonds.
Silylierte ß-Ketoncarbonsäureester wurden durch Kondensation von ß-Ketocarbonsäureestern mit Halogensilanen (vgl. USA.-Patentschrift 2 775 605), oder mit Halogenalkylsilanen (vgl. A n d r i a n o v, Lesnov, M indlin, Ber. Akad. Wiss. USSR, 94, S. 237 [1954]) hergestellt. Eine analoge Konden- sation läßt sich jedoch mit ß-Diketonen nicht durchführen. Es entstehen hierbei entweder Enolsilanolate, oder es tritt ebenfalls eine Spaltung der Siloxanbindung ein.Silylated ß-ketone carboxylic acid esters were made by condensation of ß-ketocarboxylic acid esters with halosilanes (see US Pat. No. 2,775,605), or with haloalkylsilanes (cf. A n d r i a n o v, Lesnov, M indlin, Ber. Akad. Wiss. USSR, 94, p. 237 [1954]) manufactured. An analog condenser However, sation cannot be carried out with ß-diketones. Either enol silanolates are formed here, or cleavage also occurs the siloxane bond.
Es wurde nun gefunden, daß Polysiloxane mit endstandigen Diketongruppen dadurch hergestellt werden können, daß man ein a,w-Dihydrogenpolyorganosiloxan mit mindestens 2 Mol eines a-Allylß-diketons in Gegenwart eines Platinkatalysators umsetzt. It has now been found that polysiloxanes with terminal diketone groups can be prepared by using a, w-dihydrogen polyorganosiloxane with converts at least 2 mol of an α-allyl-diketone in the presence of a platinum catalyst.
Die Reaktion verläuft dabei im Sinne einer Addition der Allylgruppe an die SiH-Endgruppen des Polysiloxans gemäß: Hierbei bedeutet n eine Zahl von 1 bis 10 und R einen Alkyl- oder Phenylrest. Solche a,w-Dihydrogenpolyorganosiloxane lassen sich nach bekannten Methoden, z. B. durch Reduktion von a,lv-Dihalogenpolyorganosiloxanen, herstellen. Die a-Allyldiketone sind durch C-Allylierung von ß-Diketonen gut zugänglich. Unter den Begriff Allyldiketone fallen auch die an der Doppelbindung alkylierten Derivate, z. B. Methallyldiketone oder Äthallyldiketone. Die Gruppen R" können gleiche oder verschiedene Kohlenwasserstoffreste sein. Beispiele für gut zugängliche a-Allyl-ß-diketonesind: 4,4-Diacetylbuten- 1, 4-4-Diacetyl-2-methylbuten- 1, 4,4-Dibenzoylbuten- 1, 4-Acetyl-4-benzoylbuten-1. Als Katalysator eignen sich Platin oder Platinverbindungen, ganz besonders Platinchlorwasserstoffsäure.The reaction proceeds in the sense of an addition of the allyl group to the SiH end groups of the polysiloxane according to: Here n is a number from 1 to 10 and R is an alkyl or phenyl radical. Such a, w-dihydrogen polyorganosiloxanes can be prepared by known methods, for. B. by reducing a, lv-Dihalogenpolyorganosiloxanen produce. The α-allyl ketones are easily accessible by C-allylation of ß-diketones. The term allyl ketones also includes the derivatives alkylated on the double bond, e.g. B. Methallyldiketone or Äthallyldiketone. The groups R "can be identical or different hydrocarbon radicals. Examples of readily accessible α-allyl-β-diketones are: 4,4-diacetylbutene-1, 4-4-diacetyl-2-methylbutene-1, 4,4-dibenzoylbutene-1 , 4-Acetyl-4-benzoylbutene-1. Suitable catalysts are platinum or platinum compounds, very particularly platinum hydrochloric acid.
Die beiden Komponenten Dihydrogensiloxan und Allyldiketon werden im Molverhältnis 1: 2 bis 1: 3 eingesetzt. Entweder führt man die Reaktion in inerten Lösungsmitteln aus, besonders gut eignet sich Diäthyläther, oder im Autoklav. Der Katalysator wird in Mengen von etwa 0,01 bis 1 Molprozent eingesetzt. In ätherischer Lösung setzt die Reaktion bei Raumtemperatur ein, wird jedoch zweckmäßigerweise durch Erwärmen beschleunigt. Da die Reaktion unter diesen Umständen quantitativ ablauft, genügt zur Aufarbeitung für viele Zwecke das Eindampfen der Lösung. Will man das Produkt frei von Platin erhalten, kann man es durch Destillation reinigen. The two components are dihydrogensiloxane and allyldiketone used in a molar ratio of 1: 2 to 1: 3. Either you carry out the reaction in inert Solvents, diethyl ether is particularly suitable, or in the autoclave. Of the Catalyst is used in amounts of about 0.01 to 1 mole percent. In more ethereal Solution starts the reaction at room temperature, but becomes expedient accelerated by heating. As the reaction under these circumstances is quantitative expires, the evaporation of the solution is sufficient for work-up for many purposes. Want if the product is obtained free of platinum, it can be purified by distillation.
Die erfindungsgemäß erhältlichen Polysiloxan-bisdiketone sind auf Grund der Tatsache, daß das Siliciumatom von den Carbonylgruppen durch 4 Kohlenstoffatome getrennt ist, stabil gegen Hydrolyse und Zersetzung beim Erhitzen bis etwa 250°C. The polysiloxane bisdiketones obtainable according to the invention are on Reason for the fact that the silicon atom is separated from the carbonyl groups by 4 carbon atoms is separated, stable against hydrolysis and decomposition when heated up to about 250 ° C.
Sie gehen die üblichen Reaktionen der ß-Diketone ein und eignen sich daher als Zwischenprodukte für die Synthese anderer difunktioneller Polysiloxane sowie zur Herstellung von makromolekularen Substanzen, die Polysiloxaneinheiten enthalten. Außerdem eignen sie sich zur Verbesserung der Haftung von Siliconlacken auf Metalloberflächen, sei es im Sinne einer Vorbehandlung der Oberfläche oder als Lackzusatz.They go into the usual reactions of the ß-diketones and are suitable therefore as intermediates for the synthesis of other difunctional polysiloxanes as well as for the production of macromolecular substances, the polysiloxane units contain. They are also suitable for improving the adhesion of silicone varnishes on metal surfaces, be it in the sense of a pretreatment of the surface or as a Paint additive.
Beispiel 1 Zu 13,4 g Tetramethyldihydrogendisiloxan, 20 ml Ather und 125 mg Platin-Kohle-Katalysator wurden innerhalb 3 Stunden 28 g Allylacetylaceton, gelöst in 260 mol Ather, getropft. Hiernach wurde das Reaktionsgemisch noch 24 Stunden unter Rühren unter Rückfluß erhitzt, der Katalysator abfiltriert und das Lösungsmittel abgedamptt. Die verbleibende gelbP liche Flüssigkeit, 31,2 g, ist die nahezu reine Verbin- dung, 1,1,2,2-Tetramethyl-1,2-bis-(4-diacetylbutyl)-disiloxan. Sie kann durch Destillation noch weitergereinigt werden. Kp.10-4, 168 bis 1700C, fl2D0 = 1,4624. Example 1 To 13.4 g of tetramethyldihydrogendisiloxane, 20 ml of ether and 125 mg of platinum-carbon catalyst were 28 g of allylacetylacetone, dissolved in 260 mol of ether, added dropwise. The reaction mixture was then left for a further 24 hours heated under reflux with stirring, the catalyst and the solvent filtered off damped. The remaining yellowish liquid, 31.2 g, is almost pure Connecting dung, 1,1,2,2-tetramethyl-1,2-bis- (4-diacetylbutyl) -disiloxane. She can get through Distillation can be further purified. Kp.10-4, 168 to 1700C, fl2D0 = 1.4624.
Analyse für C17H33O5Si: Gefunden . . . Si 1492°jo; berechnet . . Si 13,50/0.Analysis for C17H33O5Si: found. . . Si 1492 ° jo; calculated . . Si 13.50 / 0.
Beispiel 2 Die Lösung von 10,05 g 1,3-Dihydrogentetramethyldisiloxan in 50ml Äther wurde mit 25 mg H2PtCl6- 6 H20 versetzt und in dieses Gemisch innerhalb 3 Stunden die Lösung von 39,5 g Allyldibenzoylmethan in 350 ml Ather getropft. Während des Zutropfens und 75 Stunden im Anschluß hieran wurde das Reaktionsgemisch unter Rückfluß erhitzt. Danach wurde die Lösung konzentriert und der Rückstand im Wasserstrahlpumpenvakuum vom restlichen Lösungsmittel befreit. Es verblieben 50,0 g, theoretisch 49,6 g, eines schwach nach Äther riechenden gelben Oeles. Example 2 The solution of 10.05 g of 1,3-dihydrogen tetramethyldisiloxane in 50ml ether was mixed with 25 mg H2PtCl6-6H20 and in this mixture within 3 hours the solution of 39.5 g of allyldibenzoylmethane in 350 ml of ether was added dropwise. While the dropwise addition and 75 hours thereafter, the reaction mixture was under Heated to reflux. The solution was then concentrated and the residue in a water pump vacuum freed from the remaining solvent. There remained 50.0 g, theoretically 49.6 g, a yellow oil that smells faintly of ether.
Analyse für C40O5Si2: Gefunden ... C 72,2%, H 7,040/0, Si 7,89%; berechnet ... C 72,5%, H 6,84%, Si 8,45°/o.Analysis for C40O5Si2: Found ... C 72.2%, H 7.040 / 0, Si 7.89%; calculated ... C 72.5%, H 6.84%, Si 8.45%.
Beispiele 3 bis 7 Das entsprechende a,-Dihydrogensiloxan wurde mit Allylacetylaceton im Molverhältnis 1: 2 jeweils etwa 0,1 bzw. 0,2 Mol) nach Zusatz von 2 ml einer O,Olmolaren Lösung von H2PtC 6 H2O in Isopropanol in einem V2A-Autoklav nach dem Aufpressen von 30 atü Stickstoff 20 Stunden auf 160°C erhitzt. Aus diesem Reaktionsgemisch wurden die in der Tabelle aufgeführten Bis-ß-diketonsiloxane I durch fraktionierte Destillation als gelbe Flüssigkeiten erhalten. Examples 3 to 7 The corresponding α, -dihydrogensiloxane was mixed with allylacetylacetone in a molar ratio of 1: 2 in each case about 0.1 or 0.2 mol) after adding 2 ml of an 0.1 molar solution of H2PtC 6 H2O in isopropanol in a V2A After injecting 30 atmospheres of nitrogen, the autoclave was heated to 160 ° C. for 20 hours. The bis-ß-diketonsiloxanes I listed in the table were obtained from this reaction mixture as yellow liquids by fractional distillation.
Eigenschaften der Bis-ß-diketonsiloxane I
**) Nach der fraktionierten Destillation. **) After fractional distillation.
***) Als Rückstan'L***) As a residue L.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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DEB76502A DE1193504B (en) | 1964-04-24 | 1964-04-24 | Process for the preparation of polysiloxanes with terminal diketone groups |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB76502A DE1193504B (en) | 1964-04-24 | 1964-04-24 | Process for the preparation of polysiloxanes with terminal diketone groups |
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DE1193504B true DE1193504B (en) | 1965-05-26 |
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DEB76502A Pending DE1193504B (en) | 1964-04-24 | 1964-04-24 | Process for the preparation of polysiloxanes with terminal diketone groups |
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2602776A1 (en) * | 1986-08-12 | 1988-02-19 | Rhone Poulenc Chimie | BETA-CETOESTER-FUNCTIONAL DIORGANOPOLYSILOXANE USEFUL AS STABILIZING VINYL POLYCHLORIDE-BASED POLYMERS |
WO1999006471A1 (en) * | 1997-08-01 | 1999-02-11 | Ppg Industries Ohio, Inc. | Acetoacetate functional polysiloxanes |
US5916992A (en) * | 1997-08-01 | 1999-06-29 | Ppg Industries Ohio, Inc. | Polysiloxane polyols |
US5939491A (en) * | 1997-08-01 | 1999-08-17 | Ppg Industries Ohio, Inc. | Curable compositions based on functional polysiloxanes |
US6225434B1 (en) | 1997-08-01 | 2001-05-01 | Ppg Industries Ohio, Inc. | Film-forming compositions having improved scratch resistance |
US6387519B1 (en) | 1999-07-30 | 2002-05-14 | Ppg Industries Ohio, Inc. | Cured coatings having improved scratch resistance, coated substrates and methods thereto |
US6593417B1 (en) | 1999-07-30 | 2003-07-15 | Ppg Industries Ohio, Inc. | Coating compositions having improved scratch resistance, coated substrates and methods related thereto |
US6610777B1 (en) | 1999-07-30 | 2003-08-26 | Ppg Industries Ohio, Inc. | Flexible coating compositions having improved scratch resistance, coated substrates and methods related thereto |
US6623791B2 (en) | 1999-07-30 | 2003-09-23 | Ppg Industries Ohio, Inc. | Coating compositions having improved adhesion, coated substrates and methods related thereto |
US6635341B1 (en) | 2000-07-31 | 2003-10-21 | Ppg Industries Ohio, Inc. | Coating compositions comprising silyl blocked components, coating, coated substrates and methods related thereto |
US6657001B1 (en) | 1999-07-30 | 2003-12-02 | Ppg Industries Ohio, Inc. | Coating compositions having improved scratch resistance, coated substrates and methods related thereto |
-
1964
- 1964-04-24 DE DEB76502A patent/DE1193504B/en active Pending
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2602776A1 (en) * | 1986-08-12 | 1988-02-19 | Rhone Poulenc Chimie | BETA-CETOESTER-FUNCTIONAL DIORGANOPOLYSILOXANE USEFUL AS STABILIZING VINYL POLYCHLORIDE-BASED POLYMERS |
EP0263038A1 (en) * | 1986-08-12 | 1988-04-06 | Rhone-Poulenc Chimie | Beta-ketoester containing diorganopolysiloxane, and its use as a stabilizer for polyvinyl chloride |
US6136928A (en) * | 1997-08-01 | 2000-10-24 | Ppg Industries Ohio, Inc. | Curable compositions based on functional polysiloxanes |
US6541119B2 (en) | 1997-08-01 | 2003-04-01 | Ppg Industries Ohio, Inc. | Film-forming compositions having improved scratch resistance |
US5939491A (en) * | 1997-08-01 | 1999-08-17 | Ppg Industries Ohio, Inc. | Curable compositions based on functional polysiloxanes |
US5952443A (en) * | 1997-08-01 | 1999-09-14 | Ppg Industries Ohio, Inc. | Acetoacetate functional polysiloxanes |
US6040394A (en) * | 1997-08-01 | 2000-03-21 | Ppg Industries Ohio, Inc. | Curable compositions based on functional polysiloxanes |
US6046296A (en) * | 1997-08-01 | 2000-04-04 | Ppg Industries Ohio, Inc. | Curable compositions based on functional polysiloxanes |
US6048934A (en) * | 1997-08-01 | 2000-04-11 | Ppg Industries Ohio, Inc. | Curable compositions based on functional polysiloxanes |
US6054535A (en) * | 1997-08-01 | 2000-04-25 | Ppg Industries Ohio, Inc. | Acetoacetate functional polysiloxanes |
US6103838A (en) * | 1997-08-01 | 2000-08-15 | Ppg Industries Ohio, Inc. | Curable compositions based on functional polysiloxanes |
US6103824A (en) * | 1997-08-01 | 2000-08-15 | Ppg Industries Ohio, Inc. | Curable compositions based on functional polysiloxanes |
WO1999006471A1 (en) * | 1997-08-01 | 1999-02-11 | Ppg Industries Ohio, Inc. | Acetoacetate functional polysiloxanes |
US6187863B1 (en) | 1997-08-01 | 2001-02-13 | Ppg Industries Ohio, Inc. | Curable compositions based on functional polysiloxanes |
US5916992A (en) * | 1997-08-01 | 1999-06-29 | Ppg Industries Ohio, Inc. | Polysiloxane polyols |
US6274672B1 (en) | 1997-08-01 | 2001-08-14 | Ppg Industries Ohio, Inc. | Powder coating compositions containing functional polysiloxanes |
US6225434B1 (en) | 1997-08-01 | 2001-05-01 | Ppg Industries Ohio, Inc. | Film-forming compositions having improved scratch resistance |
US6534188B2 (en) | 1997-08-01 | 2003-03-18 | Ppg Industries Ohio, Inc. | Film-forming compositions having improved scratch resistance |
US6387519B1 (en) | 1999-07-30 | 2002-05-14 | Ppg Industries Ohio, Inc. | Cured coatings having improved scratch resistance, coated substrates and methods thereto |
US6593417B1 (en) | 1999-07-30 | 2003-07-15 | Ppg Industries Ohio, Inc. | Coating compositions having improved scratch resistance, coated substrates and methods related thereto |
US6610777B1 (en) | 1999-07-30 | 2003-08-26 | Ppg Industries Ohio, Inc. | Flexible coating compositions having improved scratch resistance, coated substrates and methods related thereto |
US6623791B2 (en) | 1999-07-30 | 2003-09-23 | Ppg Industries Ohio, Inc. | Coating compositions having improved adhesion, coated substrates and methods related thereto |
US6657001B1 (en) | 1999-07-30 | 2003-12-02 | Ppg Industries Ohio, Inc. | Coating compositions having improved scratch resistance, coated substrates and methods related thereto |
US6759478B2 (en) | 1999-07-30 | 2004-07-06 | Ppg Industries Ohio, Inc. | Coating compositions having improved scratch resistance, coated substrates and methods related thereto |
US6803408B2 (en) | 1999-07-30 | 2004-10-12 | Ppg Industries Ohio, Inc. | Coating compositions having improved scratch resistance, coated substrates and methods related thereto |
US6635341B1 (en) | 2000-07-31 | 2003-10-21 | Ppg Industries Ohio, Inc. | Coating compositions comprising silyl blocked components, coating, coated substrates and methods related thereto |
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