Amine functional polymers based on N-ethenylformamide

Pinschmidt, Robert K.; Wasowski, L.A.; Orphanides, G.G.; Yacoub, Khalil

doi:10.1016/0300-9440(95)00537-4

Cited by 22 publications

(28 citation statements)

References 4 publications

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“…For example, NVF was copolymerized with vinylesters, acrylates or acrylamides, followed by acid or basic treatment leading to the corresponding polyvinylamine-based copolymers. 30,31 Although straightforward, this approach requires a perfect knowledge of the comonomer reactivity ratios and close examination of the fate of the comonomer units during hydrolysis. Nevertheless, despite the possible benefits of incorporating various amino groups along the polymer chain 32,33 poly(vinylamine)-based copolymers are generally restricted to pendant primary amines.…”

Section: Introductionmentioning

confidence: 99%

Far beyond primary poly(vinylamine)s through free radical copolymerization and amide hydrolysis

et al. 2016

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Due to their affinity for many supports, their pH responsiveness, metal binding capacity and polyelectrolytes complexation, poly(vinylamine) derivatives have attracted attention for many applications including coatings, water purification, or gas membrane separation. Nevertheless, most of them possess only pendant primary amines despite the possible benefits of incorporating different amino groups along the chain. In this work, a straightforward and scalable synthesis route towards polymers bearing primary and secondary amines, as well as imidazole groups, is reported. The general strategy relies on the radical copolymerization of different vinylamides and vinyl imidazole followed by the hydrolysis of the resulting poly(vinylamide) derivatives. Binary and ternary free radical copolymerizations of Nvinylacetamide (NVA), N-methyl vinylacetamide (NMVA) and 1-vinylimidazole (VIm) were investigated and the reactivity ratios for each copolymerization system were determined. Thanks to these values a series of statistical copolymers with predictable composition and low deviation over the chain distribution could then be synthesized. Finally, the acidic hydrolysis of the acetamide functions towards the corresponding amine was performed and optimized. Copolymers containing various pendant amino groups and with low dispersity in the chain composition could be obtained, which opens new perspectives for the above mentioned applications.polyvinylimidazole 55 , as well as the dependence of the antimicrobial efficiency on the charge density and hydrophobicity. 54 Finally, these novel polyamines might also outperform primary PVAm in applications like paper strengthening or coating applications 9-11 . In other words, much can be expected from this poly(vinylamine) based synthetic platform. Notes and references

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Section: Introductionmentioning

confidence: 99%

Far beyond primary poly(vinylamine)s through free radical copolymerization and amide hydrolysis

et al. 2016

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“…Therefore, it has various applications in industries as papermaking, wastewater treatment, biological chemistry, petrochemical engineering, paint, and adhesive. [3][4][5][6][7] PVAm cannot be synthesized directly from a vinylamine monomer because of its tautomerism. It is usually synthesized by alternative methods, like Hoffmann degradation of polyacrylamide or hydrolysis of vinylamine derivatives polymer.…”

Section: Introductionmentioning

confidence: 99%

Study on the acidic hydrolysis process of poly(N‐vinylformamide/acrylonitrile) fiber

Chen

2008

J of Applied Polymer Sci

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A convenient method of preparing chelating fiber with amine groups on the fiber surface was developed. The precursor polymer of Poly(N-vinylformamide/acrylonitrile) (P(NVF/AN)) was synthesized via solution polymerization, using N-vinylforaimde as a functional monomer. The solution of P(NVF/AN) was spun through a wet spinning method and the precursor fiber was hydrolyzed in the hydrochloric acid solution to convert formamide moieties to the corresponding amine. The influence of hydrolytic conditions on hydrolysis degree, such as hydrolysis temperature, hydrolysis time, and hydrochloric acid concentrations were examined experimentally. The hydrolysis degree of the precursor fiber was evaluated by potentiometric and conductometric titrations.The changes of the structure and properties of the fibers were characterized through infrared spectroscopy, scanning electron microscopy, and tensile strength tester. The results showed that the hydrolysis degree was limited in acidic hydrolysis because of the electrostatic repulsion among the cationic amine groups and proton. The hydrolysis degree of precursor fiber reached nearly 60%, and the chelating fiber remained the adequate mechanical properties under the suitable hydrolysis condition.

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“…The copolymerization of NVF with vinyl monomers possessing electron deficient CC double bonds such as acrylates, acrylamides, or maleates yields copolymers with alternating tendencies, while copolymerization with ethylene or vinyl esters forms random types of copolymers . Alkaline hydrolysis of acrylate/NVF copolymers generates insoluble lactam polymers caused by intramolecular neighbor group reactions . A similar behavior is observed during acidic hydrolysis of acrylonitrile/NVF where amidinium structure formation takes place …”

Section: Introductionmentioning

confidence: 80%

“…Numerous publications clearly indicate the excellent copolymerization abilities of NVF . The copolymerization of NVF with vinyl monomers possessing electron deficient CC double bonds such as acrylates, acrylamides, or maleates yields copolymers with alternating tendencies, while copolymerization with ethylene or vinyl esters forms random types of copolymers .…”

Section: Introductionmentioning

confidence: 99%

Radical Copolymerization of N‐Vinylformamide with Methylvinylketone: An Approach to Iminium/Imine Ring Containing Polymers

Walther

Seifert

Hähnle

et al. 2018

Macro Chemistry & Physics

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The free radical copolymerization of N‐vinylformamide (NVF) with methylvinylketone in water and the subsequent alkaline or acidic hydrolysis produce iminium structures containing polymers. It can be concluded from the copolymerization parameters (rN ‐vinylformamide = 0.02, r methylvinylketone = 0.50) that alternating copolymers are formed which contain few amounts with statistically arranged monomer sequences. The acidic hydrolysis of the copolymer results in a water‐soluble polymer bearing five‐membered iminium rings along the polymer chain. A water‐insoluble polymer is generated under alkaline conditions also containing five‐membered imine rings. The formation of the iminium ring polymer is attributed to the fact that generated free amino groups derived from NVF immediately react with the keto groups in the vicinity. The molecular structures of the obtained polymers are characterized by 1H‐NMR, 13C‐NMR, and IR spectroscopy. The assignment of the signals in the novel polymers are confirmed by model compounds.

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Amine functional polymers based on N-ethenylformamide

Cited by 22 publications

References 4 publications

Far beyond primary poly(vinylamine)s through free radical copolymerization and amide hydrolysis

Far beyond primary poly(vinylamine)s through free radical copolymerization and amide hydrolysis

Study on the acidic hydrolysis process of poly(N‐vinylformamide/acrylonitrile) fiber

Radical Copolymerization of N‐Vinylformamide with Methylvinylketone: An Approach to Iminium/Imine Ring Containing Polymers

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