Bis-organosilane applications and synthesis

Tutkielman kirjallisuusosuudessa perehdytään organofunktionaalisiin silaaneihin. Näitä yhdisteitä käytetään kytkentäaineina komposiittien valmistuksessa sekä monessa muussa sovelluksessa, kuten hydrofobisten ja hydrofiilisten pintojen muodostamiseen, kuivausaineina, ulkoisena elektroniluovuttajana p...

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Main Author: Mills, Christopher
Other Authors: Matemaattis-luonnontieteellinen tiedekunta, Faculty of Sciences, Kemian laitos, Department of Chemistry, University of Jyväskylä, Jyväskylän yliopisto
Format: Master's thesis
Language:eng
Published: 2017
Subjects:
Online Access: https://jyx.jyu.fi/handle/123456789/53395
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author Mills, Christopher
author2 Matemaattis-luonnontieteellinen tiedekunta Faculty of Sciences Kemian laitos Department of Chemistry University of Jyväskylä Jyväskylän yliopisto
author_facet Mills, Christopher Matemaattis-luonnontieteellinen tiedekunta Faculty of Sciences Kemian laitos Department of Chemistry University of Jyväskylä Jyväskylän yliopisto Mills, Christopher Matemaattis-luonnontieteellinen tiedekunta Faculty of Sciences Kemian laitos Department of Chemistry University of Jyväskylä Jyväskylän yliopisto
author_sort Mills, Christopher
datasource_str_mv jyx
description 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.
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N\u00e4it\u00e4 yhdisteit\u00e4 k\u00e4ytet\u00e4\u00e4n kytkent\u00e4aineina komposiittien valmistuksessa sek\u00e4 monessa muussa sovelluksessa, kuten hydrofobisten ja hydrofiilisten pintojen muodostamiseen, kuivausaineina, ulkoisena elektroniluovuttajana polymeroinnissa, sek\u00e4 kosteuskovettuvien silaanimodifioitujenpolymeeriliimojen (SMP) kovettumisreaktiossa. Silaanien kosteuskovettuminen johtuu pii-atomiin (Si) sitoutuneiden ryhmien hydrolysoitumisesta kosteuden vaikutuksesta, jolloin syntyy silanoli-ryhmi\u00e4 (Si-OH), jotka voivat edelleen kondensoitua kesken\u00e4\u00e4n 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. T\u00e4ll\u00e4 voisi olla parantava vaikutus silaanikerroksen hydrolyysin kestoon tarjoamalla enemm\u00e4n tartuntapisteit\u00e4. \n\nTutkielman kokeellisessa osiossa tutkitaan nelj\u00e4n uuden bis-organosilaaniyhdisteen synteesi\u00e4. 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 sis\u00e4lt\u00e4v\u00e4\u00e4 tuoteseosta saatiin valmistettua nukleofiilisell\u00e4 substituutio- reaktiolla. Tuoteseokset karakterisoitiin 1H NMR sek\u00e4 MS-menetelmill\u00e4. Nelj\u00e4nten\u00e4 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.", "language": "fi", "element": "description", "qualifier": "abstract", "schema": "dc"}, {"key": "dc.description.abstract", "value": "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.\n\nThe 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. 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spellingShingle Mills, Christopher Bis-organosilane applications and synthesis bis-organosilane aminofunctional hydrosilylation nucleophilic substitution Orgaaninen kemia Organic Chemistry 4035
title Bis-organosilane applications and synthesis
title_full Bis-organosilane applications and synthesis
title_fullStr Bis-organosilane applications and synthesis Bis-organosilane applications and synthesis
title_full_unstemmed Bis-organosilane applications and synthesis Bis-organosilane applications and synthesis
title_short Bis-organosilane applications and synthesis
title_sort bis organosilane applications and synthesis
title_txtP Bis-organosilane applications and synthesis
topic bis-organosilane aminofunctional hydrosilylation nucleophilic substitution Orgaaninen kemia Organic Chemistry 4035
topic_facet 4035 Orgaaninen kemia Organic Chemistry aminofunctional bis-organosilane hydrosilylation nucleophilic substitution
url https://jyx.jyu.fi/handle/123456789/53395 http://www.urn.fi/URN:NBN:fi:jyu-201703291789
work_keys_str_mv AT millschristopher bisorganosilaneapplicationsandsynthesis