Photosensitive polymers with cinnamate units in the side position of chains: Synthesis, monomer reactivity ratios and photoreactivity

Mahy, Rachid; Bouammali, B.; Oulmidi, Abdelkader; Challioui, Allal; Derouet, Daniel; Brosse, Jean‐Claude

doi:10.1016/j.eurpolymj.2006.05.031

Cited by 14 publications

(7 citation statements)

References 15 publications

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“…As one can see, the initial 3 min irradiation leads to the intensity of the band slightly decrease, and the further irradiation brings about a sharp decrease, disappearing completely after 50 min irradiation. This behavior clearly indicates PVCi undergoes pho‐crosslinking due to [2 + 2] photocycloaddition between pendant cinnamate groups, which destroys the conjugation in the entire π‐electron system of lateral polymer groups [33–35]. Moreover, the photo‐crosslinking properties of PVCi also could be proved by 1 H NMR.…”

Section: Resultsmentioning

confidence: 99%

The synthesis of poly(vinyl cinnamates) and its self‐assembled structure

Liu

Zhang

et al. 2012

Polymer Engineering & Sci

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Poly(vinyl cinnamates) (PVCi) with different degrees of substitution (DS) are synthesized by grafting p‐chloro‐substituted cinnamic acid onto poly(vinyl alcohol). The chemical structures of PVCi were confirmed by 1H NMR. Amphiphilic PVCi copolymers were self‐assembled into particles in a selective solvent. The morphology and diameter of particles have been studied by scanning electron microscopic and dynamic light scattering. The morphology and hydrodynamic diameter have strong relationship with DS and water content introduced during self‐assembly process. The prepared PVCi could photo‐cross‐link at λ = 360 nm due to the photodimerization between pendant cinnamate groups. However, the self‐assembled PVCi particles did not present photo‐crosslinking behavior. The formed regular particles could disperse in aqueous solution, which increases their applications in biomedical fields. POLYM. ENG. SCI., 2013. © 2012 Society of Plastics Engineers

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Section: Resultsmentioning

confidence: 99%

The synthesis of poly(vinyl cinnamates) and its self‐assembled structure

Liu

Zhang

et al. 2012

Polymer Engineering & Sci

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“…[1,2]. Among them, of particular interest continue to be the polymers containing photo-cross-linkable cinnamate side-groups, frequently introduced via the chemical modification of some precursors, whose photochemistry, based mainly on the ability of chromophore to undergo trans-cis isomerization [3][4][5][6] and photodimerization upon UV irradiation [7][8][9], was widely exploited in the development of negative-working photoresists [10,11]. Moreover, further manipulation of the poly(vinylcinnamate) (PVCi) and its derivatives was essential for inducing various changes in the physical properties of thin polymeric films irradiated with linearly polarized light, more important for practical applicability (e.g., optical devices) being photoaligment regulation of the liquid crystals or photooptical control of the refractive index and birefringence in the film [7,[12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Polycinnamates and Block Co-polymers Prepared by Atom Transfer Radical Polymerization and Microwave Irradiation

Buruiana

Jitaru

Buruiană

et al. 2010

Designed Monomers and Polymers

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Homo-polymers of 2-cinnamoyloxyethyl methacrylate (PCEMA) and block co-polymers with methylmethacrylate (MMA) synthesized via copper(I)bromide/pentamethyldiethylentriamine-mediated atom transfer polymerization (ATRP) and microwave irradiation, under homo(co)polymerization conditions, are reported. Method 1 led to homo-polymers with relatively low molecular weight (PCEMA-1: 5100; PCEMA-2: 25 000), while the second method offered polymer of 100 000 average molecular weight (PCEMA-3), the polymerization being completed within 60 min. Two di-block co-polymers, poly(2-cinnamoyloxyethyl methacrylate-block-poly(methyl methacrylate)) ((PCEMA-b-PMMA)-1, (PCEMA-b-PMMA)-2) with 0.33 and, respectively, 0.5 molar fraction of photo-cross-linkable PCEMA were also prepared and utilized for this study. Subsequent gel-permeation chromatography (GPC) measurements on block co-polymers have indicated molecular weights of 24 000 and 45 700, respectively. In addition, structural characteristics for all photo-polymers were determined by FT-IR, 1 H-NMR, UV-Vis spectroscopy, AFM and SEM/ESEM measurements. Photochemistry in thin polymeric films suggested that UV irradiation is accompanied by an insolubilization of the film caused by the transformation of cinnamate moieties and the formation of intermolecular cross-links, with important effects on the morphology. As expected, it was found that by electrospinning the above photo-polymers produced electrospun fibers of small diameter.

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“…Synthetic chalcones are commonly synthesized with the reaction of aromatic ring bonded to acetyl group and benzaldehyde derivatives via the Claisen-Schmidt condensation in presence of bases or acids catalyst [2][3][4][5][6][7]. One of the important characteristics of the chalcones is that they have the ability to photocrosslinking under ultraviolet light [8][9][10][11][12][13]. Photochemical reactions may provoke many changes in physicochemical properties such as solubility, dielectric constant, electrical conductivity, optical transparency and refractive index [14,15].…”

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confidence: 99%

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

Aygün¹,

Çoşkun²

2018

El-Cezeri Fen Ve Mühendislik Dergisi

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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 o C. FTIR, 1 H-NMR and 13 C-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 o C. 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.

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Photosensitive polymers with cinnamate units in the side position of chains: Synthesis, monomer reactivity ratios and photoreactivity

Cited by 14 publications

References 15 publications

The synthesis of poly(vinyl cinnamates) and its self‐assembled structure

The synthesis of poly(vinyl cinnamates) and its self‐assembled structure

Polycinnamates and Block Co-polymers Prepared by Atom Transfer Radical Polymerization and Microwave Irradiation

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

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