Funkcionalizacija poli(eugenol metakrilata) s tiol-en kemijo

Oražem, Tim

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Title:	Funkcionalizacija poli(eugenol metakrilata) s tiol-en kemijo
Authors:	ID Oražem, Tim (Author) ID Paljevac, Muzafera (Mentor) More about this mentor... ID Krajnc, Peter (Comentor)
Files:	VS_Orazem_Tim_2025.pdf (3,34 MB) MD5: 0DFB4DDCE5AA92908B05D70194AC3A6A
Language:	Slovenian
Work type:	Bachelor thesis/paper
Typology:	2.11 - Undergraduate Thesis
Organization:	FKKT - Faculty of Chemistry and Chemical Engineering
Abstract:	V okviru diplomske naloge smo izvedli sintezo eugenol metakrilata (EMA), ki smo ga pripravili z esterifikacijo med hidroksilno skupino eugenola in anhidridom metakrilne kisline. Tako dobljeni monomer smo nato analizirali s Fourierjevo transformacijsko infrardečo spektroskopijo (FTIR) in jedrsko magnetno resonanco (NMR), pri čemer smo z obema metodama potrdili njegovo uspešno pripravo in ustrezno čistost. Reakcijski izkoristek se je gibal med 70 in 80%. EMA smo uporabili za sintezo visoko poroznih polimernih materialov s polimerizacijo emulzije, pri čemer smo kot zamreževalo uporabili 1,6-heksandiol diakrilat (1,6-HDDA). Dobljene polimere smo podrobno okarakterizirali z uporabo FTIR spektroskopije, elementne analize (EA) ter vrstične elektronske mikroskopije (SEM). Rezultati FTIR spektroskopije in EA so pokazali, da sta bila oba monomera uspešno vgrajena v polimerno verigo, s čimer smo potrdili učinkovito polimerizacijo. Analiza z SEM pa je razkrila tipično odprtocelično strukturo z razvito notranjo poroznostjo. Velikost por v nastalih materialih se giblje med 2,7 in 25,3 μm, odvisno od deleža zamreževala. Pore so večje v primeru 15 mol% (1,6-HDDA) in manjše v primeru 85 mol% (1,6-HDDA). V nadaljevanju smo proste alilne dvojne vezi v polimerni mreži izkoristili za funkcionalizacijo s pentaeritritol tetrakis(3-merkaptopropionatom) (PETMP). Uspešnost reakcije smo potrdili z elementno analizo, saj je bil v modificiranem polimeru zaznan delež žvepla, ki ga v osnovnem materialu ni bilo. Analiza je pokazala, da je bil delež S višji (5,7%) pri polimerih z višjim deležem EMA (85 mol%) in obratno, nižji (4,2%) pri polimerih z nižjim deležem EMA (40 mol%).
Keywords:	porozni polimeri, poliHIPE, HIP emulzija, eugenol metakrilat, 1, 6-heksandiol diakrilat, prosta verižna radikalska polimerizacija, tiol-en klik reakcija
Place of publishing:	Maribor
Publisher:	[T. Oražem]
Year of publishing:	2025
PID:	20.500.12556/DKUM-93683
UDC:	66.091.3:678.744.33(043.2)
COBISS.SI-ID:	250541315
Publication date in DKUM:	12.09.2025
Views:	178
Downloads:	36
Metadata:
Categories:	KTFMB - FKKT
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Licences

License:	CC BY-NC-ND 4.0, Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International

Link:	http://creativecommons.org/licenses/by-nc-nd/4.0/
Description:	The most restrictive Creative Commons license. This only allows people to download and share the work for no commercial gain and for no other purposes.
Licensing start date:	14.07.2025

Secondary language

Language:	English
Title:	Functionalization of poly(eugenol methacrylate) with thiol-ene chemistry
Abstract:	In this work, we synthesised eugenol methacrylate (EMA), which was prepared by esterification between the hydroxyl group of eugenol and methacrylic anhydride. The resulting monomer was analysed by Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR), both methods confirming the successful synthesis and adequate purity. The reaction yield was between 70 and 80%. EMA was then used for the synthesis of highly porous polymeric materials by emulsion polymerisation using 1,6-hexanediol diacrylate (1,6-HDDA) as crosslinker. The polymers obtained were thoroughly characterised by FTIR spectroscopy, elemental analysis (EA), and scanning electron microscopy (SEM). The results of FTIR and EA confirmed the successful incorporation of the two monomers into the polymer backbone, and thus the effective polymerisation. SEM analysis showed a typical open-cell structure with well-developed internal porosity. The pore size of the resulting materials was between 2,7 and 25,3 μm, depending on the crosslinker content. Larger pores were observed at 15 mol% (1,6-HDDA), while smaller pores were obtained at 85 mol% (1,6-HDDA). Subsequently, the free allylic double bonds within the polymer network were exploited for functionalisation with pentaerythritol tetrakis(3-mercaptopropionate) (PETMP). The success of this modification was confirmed by elemental analysis, as sulphur was detected in the functionalised polymer, whereas it was not present in the original material. The analysis also showed that the sulphur content was higher (5,7%) in polymers with a higher EMA content (85 mol%) and lower (4,2%) in those with a lower EMA content (40 mol%).
Keywords:	porous polymers, polyHIPE, HIP emulsion, eugenol methacrylate, 1, 6-hexanediol diacrylate, free radical polymerisation, thiol–ene click reaction

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