DE933230C - Process for the production of new siloxane polymers - Google Patents
Process for the production of new siloxane polymersInfo
- Publication number
- DE933230C DE933230C DED12287A DED0012287A DE933230C DE 933230 C DE933230 C DE 933230C DE D12287 A DED12287 A DE D12287A DE D0012287 A DED0012287 A DE D0012287A DE 933230 C DE933230 C DE 933230C
- Authority
- DE
- Germany
- Prior art keywords
- formula
- siloxane polymers
- production
- new siloxane
- new
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 229920000642 polymer Polymers 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229910018540 Si C Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004952 Polyamide Chemical group 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000006360 carbonyl amino methylene group Chemical group [H]N(C([*:1])=O)C([H])([H])[*:2] 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920002647 polyamide Chemical group 0.000 description 1
- WSYBLCQRXWDMSI-UHFFFAOYSA-N silyl hydrogen sulfate Chemical compound OS(=O)(=O)O[SiH3] WSYBLCQRXWDMSI-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/54—Nitrogen-containing linkages
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
Verfahren zur Herstellung von neuen Siloxanpolymeren Gegenstand der Erfindung ist die Herstellung neuer Verbindungen, die sowohl Siloxan- als auch Polyamidgruppen aufweisen und die als Überzugsstoffe dienen können.Process for the preparation of new siloxane polymers Invention is the preparation of new compounds that contain both siloxane and polyamide groups have and which can serve as coating materials.
Diese Verbindungen haben die Formel [(CH3)2SiCH,CH,CONHCH,CH,Si(CH3)20]n, worin n einen Wert von wenigstens z besitzt.These compounds have the formula [(CH3) 2SiCH, CH, CONHCH, CH, Si (CH3) 20] n, where n has a value of at least z.
Erfindungsgemäß wird zur Herstellung dieser Verbindungen ein substituiertes Triorganosilylarnid der Formel (CH3)2RSi (CH2)2CONH (CHISi (CH3)2R, worin R Phenyl oder Methyl ist, mit konzentrierter Schwefelsäure umgesetzt, wobei der Rest R an jedem Si-Atom abgespalten und ein saures Silylsulfat nebst RH gebildet wird. Dieser Ester wird dann hydrolysiert, und man erhält Verbindungen der obigen Formel.According to the invention, a substituted one is used for the preparation of these compounds Triorganosilyl amide of the formula (CH3) 2RSi (CH2) 2CONH (CHISi (CH3) 2R, where R is phenyl or methyl, reacted with concentrated sulfuric acid, the radical R on split off every Si atom and an acidic silyl sulfate is formed together with RH. This Ester is then hydrolyzed to give compounds of the above formula.
Das als Ausgangsstoff dienende Amid, dessen Herstellung hier jedoch nicht unter Patentschutz gestellt werden soll, kann durch Umsetzung eines Acylchlorides der Formel R(C H3) 2 Si C H2 C H2 C O C 1 mit einem ß-Triorganosilyl-äthylamin der Formel R(CH3)2 Si C H2 C H2 N H2 erhalten werden. Zur Umsetzung kann man die beiden Ausgangsstoffe in einem Lösungsmittel mischen, das Reaktionsprodukt säurefrei waschen und durch Destillation reinigen.The amide used as the starting material, but its production here Should not be placed under patent protection, can be done by reacting an acyl chloride of the formula R (C H3) 2 Si C H2 C H2 C O C 1 with a ß-triorganosilylethylamine of Formula R (CH3) 2 Si C H2 C H2 N H2 can be obtained. To implement you can use the two Mix the starting materials in a solvent, wash the reaction product free of acid and clean by distillation.
Beispiel z zo Gewichtsteile eines aus ß-Trimethylsilyl-äthylamin und ß-Trimethylsilyl-propionylchlorid erhaltenen Amids der Formel (CH3)3SiCH,CH@CONHCH2CH2 Si(CH3)3 werden mit 9 Gewichtsteilen konzentrierter Schwefelsäure versetzt und bei Zimmertemperatur stehengelassen. Nach wenigen Minuten setzt Gasentwicklung ein, die etwa 1/2 Stunde anhält. Nach einstündigem Erhitzen des Gemisches auf einem Dampfbad gibt man dieses langsam zu einer Lösung von Kaliumhydroxyd in absolutem Alkohol. Die Hydroxydmenge ist so bemessen, daß die Schwefelsäure neutralisiert wird. Man läßt die Mischung dann noch über Nacht stehen, filtriert sie und entfernt den Alkohol. Die zurückbleibende viskose Flüssigkeit wird mit HCl leicht angesäuert. Beim Stehen wird sie viskoser. Den so erhaltenen Stoff, der ein Polymerisat der Formel [(CH3)2SiCH,C.H,CONHCH2 C H2 S' (C H3) 2 O] ", darstellt, teilt man in zwei Teile, von denen man den einen 3 Stunden lang auf =5o° und weitere 3 Stunden auf 25o° erhitzt. Die Flüssigkeit polymerisiert dann zu einem klaren, zähen Harz, das sich kautschukartig anfühlt und zu einem dünnen Fiten ausgezogen werden kann. Der andere Teil wird 8 Stunden lang bei- 0,5 mm Druck auf 2o3° erhitzt und ergibt ein klares, braunes Harz.Example z zo parts by weight of one from ß-trimethylsilyl-ethylamine and ß-Trimethylsilyl-propionyl chloride obtained Amides of the formula (CH3) 3SiCH, CH @ CONHCH2CH2 Si (CH3) 3 are mixed with 9 parts by weight of concentrated sulfuric acid and at Left to stand at room temperature. Gas begins to develop after a few minutes, which lasts about 1/2 hour. After heating the mixture on a steam bath for an hour this is slowly added to a solution of potassium hydroxide in absolute alcohol. The amount of hydroxide is such that the sulfuric acid is neutralized. Man the mixture is then left to stand overnight, filtered and the alcohol removed. The remaining viscous liquid is slightly acidified with HCl. When standing it becomes more viscous. The substance thus obtained, which is a polymer of the formula [(CH3) 2SiCH, C.H, CONHCH2 C H2 S '(C H3) 2 O] ", is divided into two parts, one of which is Heated to 50 ° for 3 hours and to 25o ° for a further 3 hours. The liquid then polymerizes to a clear, tough resin that is rubbery to the touch and can be pulled out to a thin fit. The other part will be 8 hours heated for a long time at -0.5 mm pressure to 203 ° and gives a clear, brown resin.
Beispiel 2 Stoffe mit gleichen Eigenschaften erhält man, wenn man entsprechend dem Verfahren von Beispiel i als Ausgangsstoff die Verbindung der Formel C,H6(CH3)2SiCH2CH2CONHCH2CH2Si(CH3)2C,;Hb verwendet.Example 2 Substances with the same properties are obtained if one according to the method of Example i, the compound of the formula as starting material C, H6 (CH3) 2SiCH2CH2CONHCH2CH2Si (CH3) 2C,; Hb used.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US933230XA | 1951-05-24 | 1951-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE933230C true DE933230C (en) | 1955-09-22 |
Family
ID=22238300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED12287A Expired DE933230C (en) | 1951-05-24 | 1952-05-17 | Process for the production of new siloxane polymers |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE933230C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1218397B (en) * | 1957-05-29 | 1966-06-08 | Dow Corning A G | Process for making fibrous material water-repellent |
-
1952
- 1952-05-17 DE DED12287A patent/DE933230C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1218397B (en) * | 1957-05-29 | 1966-06-08 | Dow Corning A G | Process for making fibrous material water-repellent |
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