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Bis-organosilane applications and synthesis

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Authors
Mills, Christopher
Date
2017
Discipline
Orgaaninen kemiaOrganic Chemistry
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Tutkielman kirjallisuusosuudessa perehdytään organofunktionaalisiin silaaneihin. Näitä yhdisteitä käytetään kytkentäaineina komposiittien valmistuksessa sekä monessa muussa sovelluksessa, kuten hydrofobisten ja hydrofiilisten pintojen muodostamiseen, kuivausaineina, ulkoisena elektroniluovuttajana polymeroinnissa, sekä kosteuskovettuvien silaanimodifioitujenpolymeeriliimojen (SMP) kovettumisreaktiossa. Silaanien kosteuskovettuminen johtuu pii-atomiin (Si) sitoutuneiden ryhmien hydrolysoitumisesta kosteuden vaikutuksesta, jolloin syntyy silanoli-ryhmiä (Si-OH), jotka voivat edelleen kondensoitua keskenään muodostaen siloksaanisidoksia (Si-O-Si) tai sidoksia pintojen hydroksyyliryhmien kanssa (Si-O-M). Bis-organosilaaneilla on kaksi pii-atomikeskusta, joista kukin voi tarttua pinnan hydroksyyliryhmiin. Tällä voisi olla parantava vaikutus silaanikerroksen hydrolyysin kestoon tarjoamalla enemmän tartuntapisteitä. Tutkielman kokeellisessa osiossa tutkitaan neljän uuden bis-organosilaaniyhdisteen synteesiä. Kolmen tavoitteena olleen, N,N-bis(3-(trimetoksisilyyli)propyyli)butan-1-amiini 81, N-((trietoksisilyyli)metyyli)-N-(3-trimetoksisilyyli)propyyli)butan-1-amiini 82 ja N-((trietoksisilyyli)metyyli)-3-(trimetoksisilyyli)propan-1-amiini 83 bis-organosilaanin sisältävää tuoteseosta saatiin valmistettua nukleofiilisellä substituutio- reaktiolla. Tuoteseokset karakterisoitiin 1H NMR sekä MS-menetelmillä. Neljäntenä synteesitavoitteena olleen N-(3-(3,5-dimetoksi-5-metyyli-2,6-dioksa-3,5-disilaheptaani-3-yyli)propyyli)aniliinin 84 valmistus hydrosilylaatio-reaktiolla ei onnistunut. ...
 
The literature part of this thesis studies organofunctional silanes in depth. These compounds are used as coupling agents, to bond dissimilar substrates into composites, as well as in numerous other applications, such as preparing hydrophobic or hydrophilic surfaces, moisture scavenging, as an external electron donor during polymerization, and as the primary bonding mechanism in moisture-curing silane modified polymer (SMP) adhesives. The moisture-curing mechanism of silanes is due to the hydrolysis of one to three alkoxy or halogen leaving groups attached to silicon (Si), forming silanol ("Si-OH" ) groups which can then form siloxane ("Si-O-Si" ) or silicon surface (Si-O-M) bonds via condensation. Bis-organofunctional silane molecules have a double silicon moiety, which could increase the hydrolysis resistance of the silicon to surface interphase, by providing a respectively larger number of bonded sites. The experimental part of this thesis attempts the multiple gram scale synthesis of four novel bis-organofunctionalsilane compounds. Product mixtures that included the first three synthesis targets, N,N-bis(3-(trimethoxysilyl)propyl)butan-1-amine 81, N-((triethoxysilyl)methyl)-N-(3-trimethoxysilyl)propyl)butan-1-amine 82, N-((triethoxysilyl)methyl)-3-(trimethoxysilyl)propan-1-amine 83 were synthesized via nucleophilic substitution and achieved as determined by 1H NMR and profile or high resolution MS. The synthesis of the fourth synthesis target, N-(3-(3,5-dimethoxy-5-methyl-2,6-dioxa-3,5-disilaheptan-3-yl)propyl)aniline 84, by using hydrosilylation was not successful. ...
 
Keywords
bis-organosilane aminofunctional hydrosilylation nucleophilic substitution
URI

http://urn.fi/URN:NBN:fi:jyu-201703291789

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