Synthesis and characterization of p-benzophenoneoxycarbonylphenyl acrylate by means of experimental measurements and theoretical approaches, and bulk melt polymerization

Soykan, Uğur; Çetin, Sedat; Öztürk, Bengi Özgün; Karaboğa, Fırat; Zalaoğlu, Y.; Doğruer, M.; Terzioğlu, C.

doi:10.1016/j.molstruc.2013.07.003

Cited by 17 publications

(17 citation statements)

References 56 publications

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“…ABC was prepared by refluxing ABA, synthesized by condensation reaction of p-hydroxybenzoic acid with acryloyl chloride in alkaline medium as reported previously by Sainath et al [23], with thionyl chloride in the presence of a trace amount of dimethyl formamide for 5-6 h. In all stages, the structures of the products ABA, ABC and BPOCPA were confirmed by FTIR and 1 H-NMR techniques, and the products were characterized by DSC analysis. The results correlated well with the literature [24].…”

Section: Synthesis Of the Monomer Bpocpasupporting

confidence: 91%

“…A weak endotherm at 235°C, that can be attributed to the crystalline melting of poly(BPOCPA) domains, was observed only in the sample with 39.1 % poly(BPOCPA) among the products, although it was observed as a massive endot h e r m i n t h e t h e r m o g r a m o f t h e h o m o p o l y m e r poly(BPOCPA) at 231°C as previously reported [24]. In the coproducts, PE chains are probably interrupting the crystalline packing of poly(BPOCPA) units and thus preventing the formation of poly(BPOCPA) crystallites.…”

Section: Characterization Of the Products By Dsc And Xrdsupporting

confidence: 86%

“…This has potentially resulted in lower resistance to break. In addition, at room temperature, the poly(BPOCPA) graft units apparently have a brittle character with lower conformational ability due to comparatively high glass transition temperature, previously determined as 75°C [24]. This brittleness in nature of graft units may have considerably contributed to the facile failure of the samples, this effect was seen increasing with the content in the tests carried out at room temperature.…”

Section: Mechanical Properties Of the Productsmentioning

confidence: 92%

“…The monomer, p-benzophenoneoxycarbonylphenyl acrylate (BPOCPA) was synthesized by refluxing equimolar solution of p-acryloyloxybenzoyl chloride (ABC) and HBP in xylene for about 3-4 days as decribed in our previous work [24]. ABC was prepared by refluxing ABA, synthesized by condensation reaction of p-hydroxybenzoic acid with acryloyl chloride in alkaline medium as reported previously by Sainath et al [23], with thionyl chloride in the presence of a trace amount of dimethyl formamide for 5-6 h. In all stages, the structures of the products ABA, ABC and BPOCPA were confirmed by FTIR and 1 H-NMR techniques, and the products were characterized by DSC analysis.…”

Section: Synthesis Of the Monomer Bpocpamentioning

confidence: 99%

“…The homopolymer poly(BPOCPA) used in characterizations was obtained by both solution and bulk melt polymerizations of BPOCPA as previously described [24].…”

Section: Homo and Graft Polymerization Of Bpocpamentioning

confidence: 99%

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Reinforcement of high density polyethylene with a side chain LCP by graft copolymerization—thermal, mechanical and morphological properties

Soykan

Çetin

2015

J Polym Res

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In this study, high density polyethylene (PE) has been reinforced with a side chain LCP by graft copolymerization of p-benzophenoneoxycarbonylphenyl acrylate (BPOCPA). The mechanical and thermal behavior of the graft coproducts were investigated in relation to the structural changes (in unit cell parameters) of PE matrix. The crystalline melting temperature of PE, varying consistently with the poly(BPOCPA) content in the coproducts, significantly increased (from 131°C to 132-138°C). The unit cell dimensions, a and b, of the orthorhombic structure, the ab basal area and particle size of PE crystals initially expanded, and then consistently contracted with the graft content. The c parameter, however, remained relatively unchanged. Remarkable improvements were achieved in the tensile properties of the material; with the maxima of 38 % increase in tensile strength and 67 % increase in Young's modulus with the coproduct comprising 9.3 % poly(BPOCPA). These developments were found to be explained by the advances in the orientation and alignment of PE chains, conduced by greater chain mobility in the larger ab basal area and intensifying cohesive forces arising from the glassy nematic structured graft units.

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Section: Synthesis Of the Monomer Bpocpasupporting

confidence: 91%

Section: Characterization Of the Products By Dsc And Xrdsupporting

confidence: 86%

Section: Mechanical Properties Of the Productsmentioning

confidence: 92%

Section: Synthesis Of the Monomer Bpocpamentioning

confidence: 99%

“…The homopolymer poly(BPOCPA) used in characterizations was obtained by both solution and bulk melt polymerizations of BPOCPA as previously described [24].…”

Section: Homo and Graft Polymerization Of Bpocpamentioning

confidence: 99%

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Reinforcement of high density polyethylene with a side chain LCP by graft copolymerization—thermal, mechanical and morphological properties

Soykan

Çetin

2015

J Polym Res

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Detailed analysis on thermal, microstructural, mechanical, and morphological features of side chain liquid crystalline polymer/isotactic polypropylene graft copolymers: Effect of grafted and ungrafted polymer units

Şen

Soykan

Çetin

2020

J of Applied Polymer Sci

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5‐Ammonium‐4,4‐dimethylvaleryl (Amv) Group: Generation from Acryloyl Group through Decatungstate‐Catalyzed C(sp³)−H Addition and Removal by Base‐Triggered Cyclization

Song,

Torigoe,

Kuninobu

2023

Eur J Org Chem

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The 5‐ammonium‐4,4‐dimethylvaleryl (Amv) group was generated by conversion of acryloyl group through decatungstate‐catalyzed addition of C(sp3)−H bond of i‐BuNH2⋅HCl under the irradiation of UV light (365 nm or 405 nm). Treatment of Amv‐protected alcohols and anilines with aqueous Na2CO3 promoted the efficient deprotection of Amv. This is a unique method for the efficient removal of acryloyl groups from phenols, alcohols, and anilines. The selective removal of acryloyl groups through Amv in the presence of another acetyl or benzoyl group was demonstrated. The base‐triggered intramolecular cyclization of Amv was monitored by the release of a fluorescent molecule, and it was found that cyclization by Na2CO3 was very rapid (within 1 min) and that some weak bases such as 2,6‐lutidine are sufficient to promote cyclization.

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Synthesis and characterization of p-benzophenoneoxycarbonylphenyl acrylate by means of experimental measurements and theoretical approaches, and bulk melt polymerization

Cited by 17 publications

References 56 publications

Reinforcement of high density polyethylene with a side chain LCP by graft copolymerization—thermal, mechanical and morphological properties

Reinforcement of high density polyethylene with a side chain LCP by graft copolymerization—thermal, mechanical and morphological properties

Detailed analysis on thermal, microstructural, mechanical, and morphological features of side chain liquid crystalline polymer/isotactic polypropylene graft copolymers: Effect of grafted and ungrafted polymer units

5‐Ammonium‐4,4‐dimethylvaleryl (Amv) Group: Generation from Acryloyl Group through Decatungstate‐Catalyzed C(sp³)−H Addition and Removal by Base‐Triggered Cyclization

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Synthesis and characterization of p-benzophenoneoxycarbonylphenyl acrylate by means of experimental measurements and theoretical approaches, and bulk melt polymerization

Cited by 17 publications

References 56 publications

Reinforcement of high density polyethylene with a side chain LCP by graft copolymerization—thermal, mechanical and morphological properties

Reinforcement of high density polyethylene with a side chain LCP by graft copolymerization—thermal, mechanical and morphological properties

Detailed analysis on thermal, microstructural, mechanical, and morphological features of side chain liquid crystalline polymer/isotactic polypropylene graft copolymers: Effect of grafted and ungrafted polymer units

5‐Ammonium‐4,4‐dimethylvaleryl (Amv) Group: Generation from Acryloyl Group through Decatungstate‐Catalyzed C(sp3)−H Addition and Removal by Base‐Triggered Cyclization

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Product

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5‐Ammonium‐4,4‐dimethylvaleryl (Amv) Group: Generation from Acryloyl Group through Decatungstate‐Catalyzed C(sp³)−H Addition and Removal by Base‐Triggered Cyclization