Remarkable Effect on Thermosensitive Behavior Regarding Alkylation at the Amide Position of Poly(<i>N</i>-vinylamide)s

Kawatani, Ryo; Kan, Kai; Kelland, Malcolm A.; Akashi, Mitsuru; Ajiro, Hiroharu

doi:10.1246/cl.160145

Cited by 6 publications

(5 citation statements)

References 21 publications

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“…The insoluble part was filtered and vacuum dried, and a white powder was obtained at 59% yield (Table 1 , run 1). This result was consistent with previous research [ 39 ]. 2 was then prepared by the polymer reaction between 1 and 1-bromoethyl azobenzene with NaH in DMF.…”

Section: Resultssupporting

confidence: 94%

“…In this study, we synthesized the monomer of N -vinylamide derivatives bearing a methoxyethyl group at the N -position of NVF (MOENVF: M w = 129) in order to improve the hydrophilicity instead of hydrophobic alkyl substituents [ 39 ]. In the previous work, we have shown the length and structural isomers of alkyl substituents at the N -position of N -vinylamide copolymers, resulting in various LCST.…”

Section: Introductionmentioning

confidence: 99%

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Aggregation Control by Multi-stimuli-Responsive Poly(N-vinylamide) Derivatives in Aqueous System

et al. 2017

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Thermal and photo responsive copolymer based on N-vinylamide backbone was designed. Methoxyethyl group and azobenzene were selected to improve hydrophilicity and photoresponsive moieties, respectively. The N-(methoxyethyl)-N-vinylformamide was synthesized and copolymerized with N-vinylformamide by free radical polymerization. In order to control the nanosized structures, poly(N-vinylformamide) derivatives bearing azobenzene at the N-position near to the vinyl polymer main chain were synthesized by polymer reaction with the poly(N-vinylformamide-co-N-(methoxyethyl)-N-vinylformamide) and azobenzene. Aggregation size of the multi-stimuli-responsive polymer was controlled by preparation of the hydrophobic interaction at around N-position.Electronic supplementary materialThe online version of this article (doi:10.1186/s11671-017-2221-7) contains supplementary material, which is available to authorized users.

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Section: Resultssupporting

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Aggregation Control by Multi-stimuli-Responsive Poly(N-vinylamide) Derivatives in Aqueous System

et al. 2017

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“…This is also supported by the low yield of 12 bearing the same group as the N-position. This speculation was supported by our previous research, 42 in which the bulky side chain at the N-position influenced the polymerizability of N-vinylamide derivatives. All of the polymers were synthesized by free radical polymerization and should consist of the random copolymer sequences.…”

Section: ■ Results and Discussionsupporting

confidence: 65%

“…The thermosensitive behaviors of poly( N -vinylamide) derivatives have also been studied, such as poly( N- vinylpyrrolidone) (PNVP), − poly( N -vinylcaprolactam) (PNVC), − poly( N -vinylacetamide) (PNVA), − and others. − Among them, N -vinylacetamide (NVA) is a nonring structure unlike N -vinylpyrrolidone (NVP) or N -vinylcaprolactam (NVC), into which any functional substituent can be freely introduced. N -Vinylformamide (NVF) is also a nonring structure and is more hydrophilic than NVA. , In addition, it is known from other applications that poly( N -vinylformamide) (PNVF) and PNVA can change to cationic polyvinylamine by hydrolysis under acidic or alkali conditions .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Thermosensitive Poly(N-vinylamide) Derivatives Bearing Oligo Ethylene Glycol Chain for Kinetic Hydrate Inhibitor

Kawatani¹,

Kawata

Yusa

et al. 2018

Macromolecules

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Thermosensitive poly(N-vinylamide) derivatives bearing an oligo ethylene glycol (OEG) chain at the N-position were designed for development of a kinetic hydrate inhibitor (KHI). Novel N-vinylamide monomers bearing an OEG chain at the N-position were synthesized and copolymerized with N-vinylformamide (NVF) or methyl Nvinylacetamide (MNVA) by free radical polymerization. Then, thermosensitive behaviors, such as lower critical solution temperature (LCST), of the synthesized poly(Nvinylamide) derivatives were investigated by light transmittance and DSC measurement. The LCST values were observed over a wide temperature range from 45 to 90 °C due to the ethoxy OEG chain at the N-position. Their phase transition properties were investigated under dilute condition by light scattering measurement. Furthermore, KHI values of the synthesized polymers were evaluated by the THF hydrate crystal growth method. On the basis of these results, it is expected that the polymers of synthesized poly(N-vinylamide) derivatives will gain a prominent position in the oil industry.

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“…All of the copolymers were synthesized using a typical radical polymerization method as introduced in our previous studies. ,, Here, we take the synthesizing procedure of poly(NVF- co -nBNF) as an example and briefly introduce the copolymerization process used in this study. To a 25 mL glass flask, azobisisobutyronitrile (AIBN, 72.4 mg, 0.442 mmol) was placed.…”

Section: Methodsmentioning

confidence: 99%

Optimizing the Kinetic Hydrate Inhibition Performance ofN-Alkyl-N-vinylamide Copolymers

et al. 2018

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The generation of gas hydrates in gas and multiphase flowlines can cause blockages, leading to downtime, economic losses, and even potential accidents. Injecting kinetic hydrate inhibitors (KHIs) is an effective way to prevent gas hydrate formation. Most KHI formulations are built around water-soluble polymers containing amide groups. On the basis of past work on N-alkyl-N-vinylamide polymers from our group, we have now been able to become much closer to designing the optimum KHI for this class of polymers. In this study, we have synthesized four N-alkyl-N-vinylamide monomers, where the alkyl group is n-propyl, isopropyl, n-butyl, and isobutyl. These have been copolymerized successfully with N-methyl-N-vinylacetamide and N-vinylformamide to form a series of copolymers with low molecular weights. We have investigated their KHI performance using a slow constant cooling method with a synthetic natural gas mixture in high-pressure rocker cells at 76 bar. All of the new N-vinylamide copolymers show good KHI performance. The average onset temperature of the best copolymer, N-vinylformamide:N-isobutyl-N-vinylformamide copolymer, at 2500 ppm concentration in deionized water was 8.2 °C. This decreased considerably to 4.7 °C (ca. 15.3 °C subcooling) when 10 000 ppm of n-butyl glycol ether solvent was added, demonstrating good synergy between the polymer and solvent. Two of the best copolymers were further investigated at varying concentrations in the range of 1000–7500 ppm and showed increased performance as the dosage increased.

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Remarkable Effect on Thermosensitive Behavior Regarding Alkylation at the Amide Position of Poly(N-vinylamide)s

Cited by 6 publications

References 21 publications

Aggregation Control by Multi-stimuli-Responsive Poly(N-vinylamide) Derivatives in Aqueous System

Aggregation Control by Multi-stimuli-Responsive Poly(N-vinylamide) Derivatives in Aqueous System

Synthesis of Thermosensitive Poly(N-vinylamide) Derivatives Bearing Oligo Ethylene Glycol Chain for Kinetic Hydrate Inhibitor

Optimizing the Kinetic Hydrate Inhibition Performance ofN-Alkyl-N-vinylamide Copolymers

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