Linear Poly(N-alkylethylenimine)s

Sàegusa, Takeo; Yamada, Akira; Taoda, Hiroshi; Kobayashi, Shiro

doi:10.1021/ma60062a032

Cited by 47 publications

(33 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…For the reduction of POx to PAEI, Saegusa 4 and Hoogenboom 5 described the use of LiAlH 4 and BH 3 /DMS, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…12 This strategy does allow partial reduction of POx, but only with limited degree of control. In four different reactions, we added 30%, 30%, 50%, 70% and 150% of reduction equivalents (with respect to amide groups in the polymer) of LiAlH 4 . After 68h at 313 K, the degrees of reduction, determined by 1 H-NMR were 3, 6, 25, 46% and 100%, respectively (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…Interestingly, Micovic and Mihailovic already reported in 1955 that the reduction of tertiary amides is very fast in spite of a majority of researchers conducting the reaction for prolonged times. 12 Therefore, we investigated the kinetics of the reduction by conducting the PEtOx reduction directly in the NMR tube at 295 K. For this, 5 mg of LiAlH 4 were dispersed in 0.1 mL of THF-d 8 in a screwcap NMR tube and 10 mg of PEtOx dissolved in 0.6 mL dichloromethane were added. Immediately, NMR spectra were acquired over the course of 300 min.…”

Section: Resultsmentioning

confidence: 99%

“…However, partial reduction of POx should lead to copolymers of POx and PAEI (P(Ox-co-AEI)), but this has not been described to date. This contribution investigates the partial reduction of POx using two different reducing agents, BH 3 and LiAlH 4 . The partially reduced POx were characterized via 1 H-NMR spectroscopy, differential scanning calorimetry and acid-base titration.…”

Section: More Recently Fukuda Et Al Investigated the Solution Propementioning

confidence: 99%

“…The amide motif in the repeating unit can be reduced to a tertiary amine (Scheme 1c). [4][5] The resulting polymers are known as poly(N-alkylethylene imine)s (PAEI). PAEI can also be obtained by alkylation of PEI employing the Leuckart-Wallach reaction.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Poly(2-ethyl-2-oxazoline-co-N-propylethylene imine)s by controlled partial reduction of poly(2-ethyl-2-oxazoline)

Pfister¹,

Ringhand²,

Fetsch³

et al. 2018

Preprint

View full text Add to dashboard Cite

The partial reduction of poly(2-ethyl-2-oxazoline) was investigated. A series of poly(2-ethyl-2-oxazoline-co-N-propylethylene imine)s were synthesized by direct reduction using lithium aluminum hydride or borane/dimethylsulfide (BH 3 /DMS), respectively. It is shown that the degree of reduction can be readily controlled either by the reaction time when using an excess of LiAlH 4 or by the stoichiometry of BH 3 /DMS as was demonstrated by 1 H-NMR spectroscopy. Differential scanning calorimetry revealed that the glass transition temperature of the products decreased with increasing degree of reduction up to 25% of reduction, above which no glass transition could be detected. This control over the reduction allows the tailor synthesis of partially cationic polymers, which, in combination over the hydrophilic/lipophilic balance through the side chain length allows a tight control over materials properties. Such materials may be interesting, inter alia, for biomaterials or organic electronics.

show abstract

“…For the reduction of POx to PAEI, Saegusa 4 and Hoogenboom 5 described the use of LiAlH 4 and BH 3 /DMS, respectively.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: More Recently Fukuda Et Al Investigated the Solution Propementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Poly(2-ethyl-2-oxazoline-co-N-propylethylene imine)s by controlled partial reduction of poly(2-ethyl-2-oxazoline)

Pfister¹,

Ringhand²,

Fetsch³

et al. 2018

Preprint

View full text Add to dashboard Cite

show abstract

Cyclic Imino Ethers, Polymerization

Kobayashi

Sàegusa

2011

Encyclopedia of Polymer Science and Technology

Self Cite

View full text Add to dashboard Cite

show abstract

Poly(2‐oxazoline)‐ and Poly(2‐oxazine)‐Based Self‐Assemblies, Polyplexes, and Drug Nanoformulations—An Update

Zahoranová

Luxenhofer

2021

Adv Healthcare Materials

View full text Add to dashboard Cite

For many decades, poly(2‐oxazoline)s and poly(2‐oxazine)s, two closely related families of polymers, have led the life of a rather obscure research topic with only a few research groups world‐wide working with them. This has changed in the last five to ten years, presumably triggered significantly by very promising clinical trials of the first poly(2‐oxazoline)‐based drug conjugate. The huge chemical and structural toolbox poly(2‐oxazoline)s and poly(2‐oxazine)s has been extended very significantly in the last few years, but their potential still remains largely untapped. Here, specifically, the developments in macromolecular self‐assemblies and non‐covalent drug delivery systems such as polyplexes and drug nanoformulations based on poly(2‐oxazoline)s and poly(2‐oxazine)s are reviewed. This highly dynamic field benefits particularly from the extensive synthetic toolbox poly(2‐oxazoline)s and poly(2‐oxazine)s offer and also may have the largest potential for a further development. It is expected that the research dynamics will remain high in the next few years, particularly as more about the safety and therapeutic potential of poly(2‐oxazoline)s and poly(2‐oxazine)s is learned.

show abstract

Linear Poly(N-alkylethylenimine)s

Cited by 47 publications

References 0 publications

Poly(2-ethyl-2-oxazoline-co-N-propylethylene imine)s by controlled partial reduction of poly(2-ethyl-2-oxazoline)

Poly(2-ethyl-2-oxazoline-co-N-propylethylene imine)s by controlled partial reduction of poly(2-ethyl-2-oxazoline)

Cyclic Imino Ethers, Polymerization

Poly(2‐oxazoline)‐ and Poly(2‐oxazine)‐Based Self‐Assemblies, Polyplexes, and Drug Nanoformulations—An Update

Contact Info

Product

Resources

About