PL444474A1 - New organofunctional silatarans and new catalytic method for the synthesis of new and known organofunctional silatarans and their use as silane coupling agents for the production of rubber composites - Google Patents
New organofunctional silatarans and new catalytic method for the synthesis of new and known organofunctional silatarans and their use as silane coupling agents for the production of rubber compositesInfo
- Publication number
- PL444474A1 PL444474A1 PL444474A PL44447423A PL444474A1 PL 444474 A1 PL444474 A1 PL 444474A1 PL 444474 A PL444474 A PL 444474A PL 44447423 A PL44447423 A PL 44447423A PL 444474 A1 PL444474 A1 PL 444474A1
- Authority
- PL
- Poland
- Prior art keywords
- sup
- sub
- hydrogen atoms
- new
- organofunctional
- Prior art date
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- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
Przedmiotem zgłoszenia są nowe organofunkcyjne silatrany oraz nowy katalityczny sposób syntezy nowych i znanych organofunkcyjnych silatranów, a także ich zastosowanie jako silanowe środki sprzęgające do wytwarzania gumowych kompozytów. Nowe organofunkcyjne silatrany o ogólnym wzorze 1, w którym Z oznacza grupę o wzorze 2, w którym - Y oznacza ugrupowanie o wzorze 3, gdzie R<sup>13</sup> oznacza podstawnik alkilowy C<sub>1</sub> do C<sub>8</sub>, R<sup>1</sup> — R<sup>12</sup> oznaczają atomy wodoru; - Y oznacza Cl, R<sup>1</sup> oznacza ugrupowanie o wzorze 4, R<sup>2</sup> - R<sup>12</sup> oznaczają atomy wodoru. Sposób wytwarzania silatranów o wzorze ogólnym 1, w którym Z oznacza, - grupę o wzorze 2, w którym Y oznacza - ugrupowanie o wzorze 3, gdzie R<sup>13</sup> oznacza podstawnik alkilowy C<sub>1</sub> do C<sub>8</sub>, R<sup>1</sup> do R<sup>12</sup> oznaczają atomy wodoru - atom Cl a R<sup>1</sup> oznacza ugrupowanie o wzorze 4 oraz R<sup>2</sup> do R<sup>12</sup> oznaczają atomy wodoru; - Y oznacza Cl, H<sub>2</sub>N, NC, H<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>NH, H<sub>2</sub>C=CH(CH<sub>3</sub>)C(O)O, HS, H<sub>2</sub>NC(O)NH oraz R<sup>1</sup> do R<sup>12</sup> oznaczają atomy wodoru; - Y oznacza CH<sub>3</sub>(CH<sub>2</sub>)<sub>5</sub>CH<sub>2</sub>C(O)S oraz R<sup>1</sup>, R<sup>3</sup>, R<sup>5</sup> oznaczają grupy CH<sub>3</sub>, R<sup>2</sup>, R<sup>4</sup>, R<sup>6</sup> oraz R<sup>7</sup> - R<sup>12</sup> oznaczają atomy wodoru; - Y oznacza Cl, a R<sup>1</sup> oznacza C<sub>6</sub>H<sub>5</sub>- i R<sup>2</sup> do R<sup>12</sup> oznaczają atomy wodoru lub jeden z podstawników R<sup>7</sup> do R<sup>12</sup> oznacza grupę metylową (CH<sub>3</sub>), a pozostałe stanowią atomy wodoru lub R<sup>1</sup> i R<sup>2</sup> stanowią grupę metylową (CH<sub>3</sub>), a R<sup>3</sup> do R<sup>12</sup> oznaczają atomy wodoru lub R<sup>1</sup> i R<sup>3</sup> i R<sup>5</sup> stanowią grupę metylową (CH<sub>3</sub>), a R<sup>2</sup>, R<sup>4</sup>, R<sup>6</sup> i R<sup>7</sup> - R<sup>12</sup> oznaczają atomy wodoru; - C<sub>8</sub>H<sub>17</sub>, H<sub>2</sub>C=CH, H<sub>2</sub>C=CHCH<sub>2</sub>, Ph, CH<sub>3</sub>O oraz R<sup>1</sup> - R<sup>12</sup> oznaczają atomy wodoru - grupę o wzorze 5 oraz R<sup>1</sup> do R<sup>12</sup> oznaczają atomy wodoru, polega na tym, że poddaje się reakcji organofunkcyjnego trójalkoksysilanu o wzorze 6, w którym Z ma wyżej podane znaczenie, a R<sup>14</sup> oznacza CH<sub>3</sub> lub CH<sub>2</sub>CH<sub>3</sub> z tris(hydroksyalkilo)aminami o ogólnym wzorze 7, w którym R<sup>1</sup> — R<sup>12</sup> mają wyżej podane znaczenie w obecności katalitycznych ilości organicznych zasad azotowych o ogólnym wzorze 8, w którym E oznacza CH<sub>2</sub> lub NH lub NMe i który stanowi 1,5-diazabicyclo[4.3.0]non-5-en, 1,8-diazabicyclo[5.4.0]undec-7-en, 1,5,7-triazabicyclo[4.4.0]dec-5-en, 7-metylo-1,5,7-triazabicyclo[4.4.0]dec-5-en lub o ogólnym wzorze 9, w którym G oznacza ugrupowania NH lub N<sup>t</sup>Bu i stanowi 1,1,3,3-tetrametyloguanidynę lub 2-tert-butylo-1,1,3,3-tetrametyloguanidynę, bez użycia rozpuszczalnika. Nowe organofunkcyjne silatrany określone w zastrzeżeniu 1 do zastosowania jako silanowe środki sprzęgające do wytwarzania gumowych kompozytów.The subject of the application is new organofunctional silatrans and a new catalytic method for the synthesis of new and known organofunctional silatrans, as well as their use as silane coupling agents for the production of rubber composites. New organofunctional silatrans of the general formula 1, wherein Z is a group of the formula 2, wherein - Y is a group of the formula 3, wherein R<sup>13</sup> is an alkyl substituent C<sub>1</sub> to C<sub>8</sub>, R<sup>1</sup> — R<sup>12</sup> are hydrogen atoms; - Y is Cl, R<sup>1</sup> is a group of the formula 4, R<sup>2</sup> - R<sup>12</sup> are hydrogen atoms. A method for producing silatranes of the general formula 1, wherein Z denotes - a group of the formula 2, wherein Y denotes - a group of the formula 3, wherein R<sup>13</sup> denotes a C<sub>1</sub> to C<sub>8</sub> alkyl substituent, R<sup>1</sup> to R<sup>12</sup> denote hydrogen atoms - Cl atom and R<sup>1</sup> denotes a group of the formula 4 and R<sup>2</sup> to R<sup>12</sup> denote hydrogen atoms; - Y represents Cl, H<sub>2</sub>N, NC, H<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>NH, H<sub>2</sub>C=CH(CH<sub>3</sub>)C(O)O, HS, H<sub>2</sub>NC(O)NH and R<sup>1</sup> to R<sup>12</sup> represent hydrogen atoms; - Y denotes CH<sub>3</sub>(CH<sub>2</sub>)<sub>5</sub>CH<sub>2</sub>C(O)S and R<sup>1</sup>, R<sup>3</sup>, R<sup>5</sup> denote CH<sub>3</sub>, R<sup>2</sup>, R<sup>4</sup>, R<sup>6</sup> and R<sup>7</sup> groups - R<sup>12</sup> denote hydrogen atoms; - Y is Cl, and R<sup>1</sup> is C<sub>6</sub>H<sub>5</sub>- and R<sup>2</sup> to R<sup>12</sup> are hydrogen atoms or one of the substituents R<sup>7</sup> to R<sup>12</sup> is a methyl group (CH<sub>3</sub>), and the others are hydrogen atoms or R<sup>1</sup> and R<sup>2</sup> are a methyl group (CH<sub>3</sub>), and R<sup>3</sup> to R<sup>12</sup> are hydrogen atoms or R<sup>1</sup> and R<sup>3</sup> and R<sup>5</sup> are a methyl group (CH<sub>3</sub>), and R<sup>2</sup>, R<sup>4</sup>, R<sup>6</sup> and R<sup>7</sup> - R<sup>12</sup> represent hydrogen atoms; - C<sub>8</sub>H<sub>17</sub>, H<sub>2</sub>C=CH, H<sub>2</sub>C=CHCH<sub>2</sub>, Ph, CH<sub>3</sub>O and R<sup>1</sup> - R<sup>12</sup> denote hydrogen atoms - a group of formula 5 and R<sup>1</sup> to R<sup>12</sup> denote hydrogen atoms, consists in reacting an organofunctional trialkoxysilane of formula 6, where Z has the meaning given above, and R<sup>14</sup> denotes CH<sub>3</sub> or CH<sub>2</sub>CH<sub>3</sub> with tris(hydroxyalkyl)amines of the general formula 7, where R<sup>1</sup> — R<sup>12</sup> have the meaning given above in in the presence of catalytic amounts of organic nitrogen bases of the general formula 8, wherein E represents CH<sub>2</sub> or NH or NMe and is 1,5-diazabicyclo[4.3.0]non-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene or of the general formula 9, wherein G represents NH or N<sup>t</sup>Bu groups and is 1,1,3,3-tetramethylguanidine or 2-tert-butyl-1,1,3,3-tetramethylguanidine, without using a solvent. Novel organofunctional silatrans as defined in claim 1 for use as silane coupling agents in the production of rubber composites.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL444474A PL248502B1 (en) | 2023-04-18 | 2023-04-18 | Silatrans, method of obtaining them and use as silane coupling agents for the production of rubber composites |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL444474A PL248502B1 (en) | 2023-04-18 | 2023-04-18 | Silatrans, method of obtaining them and use as silane coupling agents for the production of rubber composites |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL444474A1 true PL444474A1 (en) | 2024-10-21 |
| PL248502B1 PL248502B1 (en) | 2025-12-22 |
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ID=93155128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL444474A PL248502B1 (en) | 2023-04-18 | 2023-04-18 | Silatrans, method of obtaining them and use as silane coupling agents for the production of rubber composites |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL248502B1 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1328006A (en) * | 1970-03-18 | 1973-08-22 | Vyzk Ustav Organ Syntez | Carbo-functional derivatives of silatranes and a process for producing same |
| CA1044698A (en) * | 1975-04-23 | 1978-12-19 | Mikhail G. Voronkov | Process for the production of 1-organyl-silatranes and carbofunctional derivatives thereof |
| EP0919558A2 (en) * | 1997-11-28 | 1999-06-02 | Dow Corning Toray Silicone Company, Ltd. | Silatrane derivative, method for manufacturing same, adhesion promoter, and curable silicone compositions |
-
2023
- 2023-04-18 PL PL444474A patent/PL248502B1/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1328006A (en) * | 1970-03-18 | 1973-08-22 | Vyzk Ustav Organ Syntez | Carbo-functional derivatives of silatranes and a process for producing same |
| CA1044698A (en) * | 1975-04-23 | 1978-12-19 | Mikhail G. Voronkov | Process for the production of 1-organyl-silatranes and carbofunctional derivatives thereof |
| EP0919558A2 (en) * | 1997-11-28 | 1999-06-02 | Dow Corning Toray Silicone Company, Ltd. | Silatrane derivative, method for manufacturing same, adhesion promoter, and curable silicone compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| PL248502B1 (en) | 2025-12-22 |
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