Synthesis of a nonionic polymer surfactant from cyclic imino ethers by the terminator method

Kobayashi, Shiro; Uyama, Hiroshi; Higuchi, Noriko; Sàegusa, Takeo

doi:10.1021/ma00203a011

Cited by 38 publications

(16 citation statements)

References 3 publications

(7 reference statements)

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“…Poly(2-methyl-2-oxazoline) (PMOZ) was prepared according to the literature. 9 Poly(vinyl alcohol) (PVA, degree of saponification: 88%) was kindly donated by Kuraray Co., Ltd. Other reagents and solvents were commercially available and were used as received.…”

Section: Methodsmentioning

confidence: 99%

Enzymatic Template Polymerization of Phenol in the Presence of Water-soluble Polymers in an Aqueous Medium

Kim

Uyama

Kobayashi

2004

Polym J

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ABSTRACT:The enzymatic polymerization of phenol was investigated by using water-soluble polymers (WSPs) as template in an aqueous medium. The addition of PEG, one of WSPs, produced a miscible complex of polyphenol and PEG as precipitates in high yields. CD measurement verified the formation of a phenol-PEG complex by hydrogen bonding interaction. The presence of PEG in an aqueous medium greatly improved the regioselectivity of the polymerization, yielding a polyphenol with the phenylene unit content higher than 90%. The amount of PEG strongly affected the polyphenol yield. The unit molar ratio of polyphenol and PEG was ca. 1:1. The FT IR, DSC, and XRD analyses exhibited the formation of the miscible complex of polyphenol and PEG by hydrogen bonding interaction. [DOI 10.1295/polymj.36.992] KEY WORDS Enzymatic Polymerization / Poly(ethylene glycol) / Polyphenol / Regioselectivity / Template Polymerization / Water-soluble Polymer / Polymerization of a monomer in the presence of a preformed macromolecule is usually defined as template polymerization.1 The presence of the template can influence the polymerization rate of the monomer with respect to the blank polymerization and also properties of the final product such as molecular weight and stereoregularity. Template polymerization leads to formation of polymer-polymer complexes stabilized via noncovalent binding forces like electrostatic interactions, hydrogen bonds, hydrophobic interactions, and stereocomplexation.2 It is accepted that template polymerization proceeds according to two different mechanisms, zip and pick-up mechanisms. 1 Usually, when the monomers are connected with the template by strong forces such as hydrogen and electrostatic bonds, the polymerization starts through a zip mechanism.1,2 However, strict control of the free radical polymerization by using the template has not successfully been achieved even in the case of a linear template polymer with a narrow molecular weight distribution. This is probably because the free radical polymerization is randomly initiated in the template.Recently, enzymatic syntheses of phenolic polymers have received much attention as an alternative process for preparing conventional phenolic resins without the use of toxic formaldehyde, a monomer for production of conventional phenolic resins (phenol-formaldehyde resins).3 So far, a new class of useful and high-performance polyphenols have been prepared by utilizing characteristic catalysis of enzymes, most of which can not be obtained by conventional chemical methods. 4 In the enzymatic oxidative polymerization of phenol derivatives, however, control of the coupling selectivity (regioselectivity) is often very difficult, since the reaction proceeds via coupling of free radical intermediates. From phenol, the simplest and most important phenolic compound in industrial fields, a soluble polyphenol consisting of a mixture of phenylene and oxyphenylene units was synthesized in a mixture of methanol and phosphate buffer (Scheme 1). 5 The regioselectivity depended on ...

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Section: Methodsmentioning

confidence: 99%

Enzymatic Template Polymerization of Phenol in the Presence of Water-soluble Polymers in an Aqueous Medium

Kim

Uyama

Kobayashi

2004

Polym J

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“…The polymer surfactants FP x L n , with a hydrocarbon and a fluorocarbon end group where x denotes the degree of polymerization and n the length of the hydrocarbon end group were prepared by a combination of initiator 32) and terminator method 28,34) . The synthesis of the lipophilic termination reagents was carried out according to Scheme 2.…”

Section: Polymer Synthesismentioning

confidence: 99%

Design and synthesis of a two compartment micellar system based on the self-association behavior of poly(N-acylethyleneimine) end-capped with a fluorocarbon and a hydrocarbon chain

Weberskirch

Preuschen

Spiess

et al. 2000

Macromol. Chem. Phys.

101

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“…α,ω-Homo- and heterofunctional telechelics can be obtained by combining the initiator [22] and termination [23] method. The majority of researchers typically terminate using water or OH − , which leaves a –OH terminus.…”

Section: Introductionmentioning

confidence: 99%

“…Alternatively, hydrophilic POx can be combined with hydrophobic moieties such as long alkyl chains or lipids by the initiation [22] or termination [23] method to yield defined non-ionic surfactants. This has been used frequently for the design of lipopolymers of defined hydrophilic-lipophilic balance for model membrane constructs.…”

Section: Introductionmentioning

confidence: 99%

“…A direct approach is to use initiator multiplicity to control the polymer architecture which also allows to add terminal functionalities, such as drug-targeting moieties at the chain ends by the termination method. [23], [86] Mono- and difunctional initiators yield linear symmetric or asymmetric telechelic polymers. [15], [87] while higher plurifunctional initiators give tri-, tetra- etc.…”

Section: Introductionmentioning

confidence: 99%

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Poly(2‐oxazoline)s as Polymer Therapeutics

Luxenhofer

Han

Schulz

et al. 2012

Macromol. Rapid Commun.

422

325

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Poly(2-oxazoline)s (POx) are currently discussed as an upcoming platform for biomaterials design and especially for polymer therapeutics. POx meets several requirements needed for the development of next-generation polymer therapeutics such as biocompatibility, high modulation of solubility, variation of size, architecture as well as chemical functionality. Although in the early 1990s first and promising POx-based systems were presented but the field lay dormant for almost two decades. Only very recently, POx based polymer therapeutics came back into the focus of very intensive research. In this review, we give an overview on the chemistry and physicochemical properties of POx and summarize the research of POx-protein conjugates, POx-drug conjugates, POx-based polyplexes and POx micelles for drug delivery.

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Synthesis of a nonionic polymer surfactant from cyclic imino ethers by the terminator method

Cited by 38 publications

References 3 publications

Enzymatic Template Polymerization of Phenol in the Presence of Water-soluble Polymers in an Aqueous Medium

Enzymatic Template Polymerization of Phenol in the Presence of Water-soluble Polymers in an Aqueous Medium

Design and synthesis of a two compartment micellar system based on the self-association behavior of poly(N-acylethyleneimine) end-capped with a fluorocarbon and a hydrocarbon chain

Poly(2‐oxazoline)s as Polymer Therapeutics

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