Poly[4-pyridinyl-4´-(2-methacryloyloxyethoxy)styryl ketone-co-2- hydroxypropyl methacrylate]: Synthesis, Characterization, Thermal and Electrical properties, and Photocrosslinking behavior

Abstract

Synthesis of a chalcone bearing pyridine ring, 4-pyridinyl-4´-(2-hydroxyethoxy)styryl ketone, was carried out from the reaction of 4-acetyl pyridine and 4-(2-hydroxyetoxy)benzaldehyde in an aqueous solution of NaOH. 4-Pyridinyl-4´-(2-methacryloyloxyethoxy)styryl ketone which is the methacrylate monomer bearing chalcone structure in side chain, was obtained from acylation of 4-pyridinyl-4´-(2-hydroxyethoxy)styryl ketone with methacryloyl chloride in the cold. The copolymer of 4-pyridinyl-4´-(2-methacryloyloxyethoxy)styryl ketone and 2-hydroxypropyl methacrylate was prepared by free radical polymerization in presence of AIBN at 70 oC. FTIR, 1H-NMR and 13C-APT spectroscopic techniques were used for structural characterization of the Chalcone, the monomer and the copolymer. Thermal characterization of the copolymer was carried out using DSC and TGA techniques. DSC curve shows that this copolymer has a glass transition temperature of 78 oC. The TGA curve shows that decomposition given volatile product started at 230 °C and a residue of 21% left at 500 °C. Dielectric constant (ε´) of the copolymer decreased rapidly from 8.8 to 4.2 with increasing frequency in the range of 100-1000 Hz, and after this frequency ε´ quantity remained constant at a value such as 4.2. ε´ Value of the copolymer increased only from 4.2 to 4.9 with increasing from 290 K to 385 K. The AC conductivity of the copolymer increases from 5.01x10-10 S/cm to 126.0x10-10 S/cm as the frequency increase from 100 Hz to 5000 Hz. The AC conductivity increases slightly with increasing temperature, 2.52x10-9 S/cm at 300 K, and 2.89x10-9 S/cm at 385 K. After a solution of the copolymer was irradiated using UV light at 365 nm at room temperature, the absorption band at 356 nm disappeared and a new band was seen at 284 nm.

Keywords

• chalcone
• photocrosslink
• thermal properties
• conductivity
• dielectric constant

Poli[4-piridinil-4´-(2-metakriloiloksietoksi)stiril keton-ko-2-hidroksipropil metakrilat]: Sentezi, Karakterizasyonu, Termal ve Elektriksel Özellikleri ve Fotoçaprazbağlanma Davranışı

Abstract

Piridin halkası taşıyan kalkonun sentezi, 4-piridinil-4´-(2-hidroksietoksi)stiril keton, 4-asetil piridin ve 4-(2-hidroksietoksi)benzaldehitin NaOH in sulu çözeltisinde reaksiyonundan gerçekleştirildi. Yan zincirinde kalkon yapısı taşıyan bir metakrilat monomeri olan 4-piridinil-4´-(2-metakriloiloksietoksi)stiril keton, 4-piridinil-4´-(2-hidroksietoksi)stiril ketonun metakriloil klorürle soğukta açillenmesinden elde edildi. 4-piridinil-4´-(2-metakriloiloksietoksi)stiril keton ve 2-hidroksipropil metakrilatın kopolimeri, AİBN yanında 70 oC de serbest radikal polimerizasyonuyla elde edildi. Kalkon, monomer ve kopolimerin yapısal karakterizasyonunda FTIR, 1H-NMR ve 13C-APT spektroskopik teknikleri kullanıldı. Kopolimerin termal karakterizasyonu DSC ve TGA teknikleriyle gerçekleştirildi. DSC eğrisi kopolimerin camsı geçiş sıcaklığının 78 oC olduğunu gösterdi. TGA eğrisi uçucu madde veren temel parçalanmanın 230 oC de başladığını ve 500 oC de %21 artık bıraktığını gösterdi. Kopolimerin dielektrik sabiti (ε´) 100-1000 Hz aralığında artan frekansla 8.8 den 4.2 ye hızla düştü ve bu frekanstan sonra ε´ niceliği 4.2 gibi bir değerdeDielectric constant (ε´) of the copolymer decreased rapidly from 8.8 to 4.2 with increasing frequency in the range of 100-1000 Hz, and after this frequency ε´ quantity remained constant at a value such as 4.2. ε´ Value of the copolymer increased only from 4.2 to 4.9 with increasing from 290 K to 385 K. The AC conductivity of the copolymer increases from 5.01x10-10 S/cm to 126.0x10-10 S/cm as the frequency increase from 100 Hz to 5000 Hz. The AC conductivity increases slightly with increasing temperature, 2.52x10-9 S/cm at 300 K, and 2.89x10-9 S/cm at 385 K. After a solution of the copolymer was irradiated using UV light at 365 nm at room temperature, the absorption band at 356 nm disappeared and a new band was seen at 284 nm. sabit kaldı. Kopolimerin ε´ değeri, sıcaklık 290 K den 385 K e artarken sadece 4.2 den 4.9´a yükseldi. Kopolimerin AC iletkenliği, frekansın 100 Hz´den 5000 Hz´e çıkmasıyla 5.01x10-10 S/cm´den 126.0x10-10 S/cm´ye arttı. AC iletkenliği artan sıcaklıkla çok az yükseldi, 300 K´de 2.52x10-9 S/cm ve 385 K´de 2.89x10-9 S/cm. Kopolimerin bir çözeltisi 365 nm dalga boylu UV ışığa maruz bırakıldığında 356 nm´deki band kayboldu ve 284 nm´de yeni bir band oluştu.

Keywords

• Kalkon
• fotoçapraz bağlanma
• termal özellikler
• iletkenlik
• dielektrik sabiti

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