Thermoresponsive Copolymers of Ethylene Oxide and <i>N,N</i>‐Diethyl Glycidyl Amine: Polyether Polyelectrolytes and PEGylated Gold Nanoparticle Formation

Reuss, Valerie S.; Werre, Mathias; Frey, Holger

doi:10.1002/marc.201200307

Cited by 23 publications

(66 citation statements)

References 27 publications

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“…Starting materials are easily accessible and common in chemical industry which renders these materials interesting for different applications. The functional epoxide is obtained via intramolecular nucleophilic substitution (S N i) when ECH and the respective alcohol or amine are used as the starting materials . Another route is the protection of the hydroxyl group of glycidol with ethyl vinyl ether under acidic catalysis …”

Section: Poly(epoxide)smentioning

confidence: 99%

“…N,N ‐dibenzyl glycidyl amine (DBAG) and N,N ‐diallyl glycidyl amine (DAGA) carry protected amines which can be deprotected after polymerization and enable the introduction of free amine moieties. The use of N,N ‐diethyl glycidyl amine (DEGA), N,N ‐di( n ‐alkyl) glycidyl amines (DXGA), and N,N ‐diisopropyl amino ethyl glycidyl ether (DEGE) allows the synthesis of cationic polyelectrolytes as the amine groups can be quaternized.…”

Section: Poly(epoxide)smentioning

confidence: 99%

“…Under certain reaction conditions the copolymerization of glycidyl derivatives with EO is perfectly random, but also gradient copolymers, especially for the amino‐derivatives have been reported …”

Section: Poly(epoxide)smentioning

confidence: 99%

“…The functional epoxide is obtained via intramolecular nucleophilic substitution (S N i) when ECH and the respective alcohol or amine are used as the starting materials. [53][54][55][56][57][58][59] Another route is the protection of the hydroxyl group of glycidol with ethyl vinyl ether under acidic catalysis. [ 60 ] The random copolymerization of EO and functional epoxides ( Figure 6 ) enables further modifi cation of the PEG backbone.…”

Section: Multifunctional Poly(ethylene Glycol)smentioning

confidence: 99%

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Aliphatic Polyethers: Classical Polymers for the 21st Century

Klein

Wurm

2015

Macromol. Rapid Commun.

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Polyethers-polymers with the structural element (R'-O-R)n in their backbone--are an old class of polymers which were already used at the time of the ancient Egyptians. However, still today these materials are highly important with applications in all areas of our life, reaching from the automotive and paper industry to cosmetics and biomedical applications. In this Review, different aliphatic polyethers like poly(epoxide)s, poly(oxetane)s, and poly(tetrahydrofuran) are discussed. Special emphasis is placed on the history, the polymerization techniques (industrially and in academia), the properties, the applications as well as recent developments of these materials.

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Section: Poly(epoxide)smentioning

confidence: 99%

Section: Poly(epoxide)smentioning

confidence: 99%

Section: Poly(epoxide)smentioning

confidence: 99%

Section: Multifunctional Poly(ethylene Glycol)smentioning

confidence: 99%

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Aliphatic Polyethers: Classical Polymers for the 21st Century

Klein

Wurm

2015

Macromol. Rapid Commun.

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“…11–13 The incorporation of pH-sensitive groups enables tuning the cloud-point temperature, and triggering micellization or hydrogelation by changes in pH. 5,12–19 Specifically for some applications in biomedical materials, transitions with pH must occur within the window of physiologically-relevant pH variation of ca . pH 5.0–7.4.…”

Section: Introductionmentioning

confidence: 99%

Physiologically relevant, pH-responsive PEG-based block and statistical copolymers with N,N-diisopropylamine units

et al. 2013

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In order to impart pH-responsiveness within a physiologically-relevant context to PEG-based biomaterials, a new tertiary amine containing repeat unit, N,N-diisopropyl ethanolamine glycidyl ether (DEGE), was developed and incorporated into statistical and block copolymers with ethylene oxide (EO), and allyl glycidyl ether (AGE) via anionic ring-opening polymerization. The reactivity of this novel monomeric building block in copolymerizations with EO was investigated by spectroscopy with observed reactivity ratios of rDEGE = 1.28 ± 0.14 and rEO = 0.82 ± 0.10. It was further demonstrated that DEGE containing copolymers could serve as building blocks for the formation of new pH-responsive materials with a pKa of ca. 9, which allowed macroscopic hydrogels to be prepared from symmetric triblock copolymers PDEGE5.3k-b-PEO20k-b-PDEGE5.3k. The triblock copolymers exhibited clear sol-to-gel transitions in a physiologically-relevant critical gelation range of pH 5.8–6.6 and pH-dependent viscoelastic properties. On the nanometer scale, the preparation of pH-responsive micro- or nanogels was demonstrated by crosslinking P(DEGE-co-AGE) copolymers in miniemulsion droplets stabilized by PEO-b-P(DEGE-co-AGE) diblock terpolymers. These nanoparticles exhibited a reversible pH-dependent swelling profile with a volume phase transition at physiological pH 6.5–7.5.

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Aminal Protection of Epoxide Monomer Permits the Introduction of Multiple Secondary Amine Moieties at Poly(ethylene glycol)

Blankenburg

Frey

2019

Macromol. Rapid Commun.

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In contrast to acetal groups, aminal moieties are almost unknown in polymer chemistry. The aminal‐protected isopropyl‐hexahydro‐pyrimidine glycidyl amine (PyGA) for the anionic ring‐opening polymerization (AROP) is introduced. The monomer is prepared in a two‐step synthesis and can be polymerized in a well‐controlled manner under AROP conditions. Several poly(ethylene glycol) block and triblock copolymers are synthesized in a molecular weight range from 2 700 to 11 400 g mol−1 with up to 11 mol% PyGA. The molecular weight distributions are monomodal with low dispersity (Đ = Mw/Mn) below 1.2. After the polymerization, the acid‐labile hexahydro‐pyrimidine rings can be conveniently cleaved in acidic media, liberating two secondary amines per PyGA monomer unit. The released 1,3‐diamine functionalities can be addressed via post‐polymerization modification and show complexation of copper(II) ions in aqueous solution. The compounds are promising for water‐soluble catalyst systems, the removal of transition metals from water, and as a building block for complexing polyethers for biomedical application.

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Thermoresponsive Copolymers of Ethylene Oxide and N,N‐Diethyl Glycidyl Amine: Polyether Polyelectrolytes and PEGylated Gold Nanoparticle Formation

Cited by 23 publications

References 27 publications

Aliphatic Polyethers: Classical Polymers for the 21st Century

Aliphatic Polyethers: Classical Polymers for the 21st Century

Physiologically relevant, pH-responsive PEG-based block and statistical copolymers with N,N-diisopropylamine units

Aminal Protection of Epoxide Monomer Permits the Introduction of Multiple Secondary Amine Moieties at Poly(ethylene glycol)

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