Intrinsic Green Fluorescent Cross-Linked Poly(ester amide)s by Spontaneous Zwitterionic Copolymerization
Aadarash ZiaJohn R. FinneganJoshua P. MorrowWenping YinJacek J. JasieniakEmily PentzerStuart C. ThickettThomas P. DavisKristian Kempe
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The spontaneous zwitterionic copolymerization (SZWIP) of 2-oxazolines and acrylic acid affords biocompatible but low molecular weight linear N-acylated poly(amino ester)s (NPAEs). Here, we present a facile one-step approach to prepare functional higher molar mass cross-linked NPAEs using 2,2′-bis(2-oxazoline)s (BOx). In the absence of solvent, insoluble free-standing gels were formed from BOx with different length n-alkyl bridging units, which when butylene-bridged BOx was used possessed an inherent green fluorescence, a behavior not previously observed for 2-oxazoline-based polymeric materials. We propose that this surprising polymerization-induced emission can be classified as nontraditional intrinsic luminescence. Solution phase and oil-in-oil emulsion approaches were investigated as means to prepare solution processable fluorescent NPAEs, with both resulting in water dispersible network polymers. The emulsion-derived system was investigated further, revealing pH-responsive intensity of emission and excellent photostability. Residual vinyl groups were shown to be available for modifications without affecting the intrinsic fluorescence. Finally, these systems were shown to be cytocompatible and to function as fluorescent bioimaging agents for in vitro imaging.Keywords:
Oxazoline
Molar mass
Acrylic acid
Emulsion polymerization
Cationic polymerization
Abstract Poly(2‐alkyl‐2‐oxazoline)s (PAOx) are regaining interest for biomedical applications. However, their full potential is hampered by the inability to synthesise uniform high‐molar mass PAOx. In this work, we proposed alternative intrinsic chain transfer mechanisms based on 2‐oxazoline and oxazolinium chain‐end tautomerisation and derived improved polymerization conditions to suppress chain transfer, allowing the synthesis of highly defined poly(2‐ethyl‐2‐oxazoline)s up to ca. 50 kDa (dispersity ( Ð ) <1.05) and defined polymers up to at least 300 kDa ( Ð <1.2). The determination of the chain transfer constants for the polymerisations hinted towards the tautomerisation of the oxazolinium chain end as most plausible cause for chain transfer. Finally, the method was applied for the preparation of up to 60 kDa molar mass copolymers of 2‐ethyl‐2‐oxazoline and 2‐methoxycarbonylethyl‐2‐oxazoline.
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Using Gemini cationic M and other auxiliaries mixed together,such as 1815 and Poly-cationic S,the influence of the Cationic dye on the dyeing property of Modified Polyester CDP and ECDP was studied,and the interaction between Gemini cationic M and dyes were investigated.The results indicated that Gemini cationic M could be used as the retarding agents of ECDP;however,there was little effect on CDP,the difference of retarding effect was related to the high surface activity on Gemini cationic M.
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Abstract It is commonly known that cationic and anionic surfactants cannot be mixed without the risk of precipitation or instability. However, many studies have shown that not only is it possible to combine cationic and anionic surfactants, but also that this combination can present synergic properties. Mixtures of anionic and cationic surfactants have many unique properties that can be very useful when used properly. The aim of this report is to present relevant information concerning the interaction between anionic and cationic surfactants. A bibliographic review on anionic/cationic mixtures is presented here in order to better understand their properties and possible synergic effects, as this is of practical importance for the chemical industry.
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Poly(2-alkyl-2-oxazoline)s (PAOx) are regaining interest for biomedical applications. However, their full potential is hampered by the inability to synthesise uniform high-molar mass PAOx. In this work, we proposed alternative intrinsic chain transfer mechanisms based on 2-oxazoline and oxazolinium chain-end tautomerisation and derived improved polymerization conditions to suppress chain transfer, allowing the synthesis of highly defined poly(2-ethyl-2-oxazoline)s up to ca. 50 kDa (dispersity (Ð) <1.05) and defined polymers up to at least 300 kDa (Ð<1.2). The determination of the chain transfer constants for the polymerisations hinted towards the tautomerisation of the oxazolinium chain end as most plausible cause for chain transfer. Finally, the method was applied for the preparation of up to 60 kDa molar mass copolymers of 2-ethyl-2-oxazoline and 2-methoxycarbonylethyl-2-oxazoline.
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This paper based on acrylic ester as the main monomer synthesized the cationic polymer emulsion by emulsion polymerization methods.The effect of emulsifier,initiator,the polymerization process of emulsion,and the change of the kind of functional monomer and reactive monomer on cationic polymer emulsion are explored.The results indicate,when cationic emulsifier adopts 31527,the amount of emulsifier is 5% of the total mass of monomer,the micro-emulsion polymerization is used,cationic emulsifier: non-ionic emulsifier=4:1(mass ratio),the dosage of cationic initiator is 0.5%,the monomer can well copolymerize and the properties of emulsion are better.
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Abstract An in‐depth study on the kinetics of the cationic emulsion polymerization of styrene in a batch reactor is presented. This study is focused on the effect of the amount of the cationic surfactant dodecyltrimethylammonium bromide (DTAB), using two different cationic initiators: 2,2′‐azobisisobutyramidine dihydrochloride (AIBA), 2,2′‐azobis ( N , N ′‐dimethyleneisobutyramidine) dihydrochloride (ADIBA), on kinetics and colloidal features such as conversion, number of particles, number average of radicals per particle, mean particle diameter, and particle size distribution (PSD) of the polystyrene latices obtained by emulsion polymerization in a batch reactor. Furthermore, the results of the cationic emulsion polymerization were compared with its homologous anionic case. Using DTAB as cationic surfactant an expected increase in the total rate of polymerization was observed when the DTAB concentration increased. However, the total number of particles increased much more than in the anionic system. On the other hand, a dependence on the particle size of the rate of polymerization per particle together with the average number of radicals per particle was found. These differences between cationic and anionic emulsion polymerizations were explained taking into account the limited particle coagulation observed with cationic surfactants, and the high rate of radical formation of cationic initiators. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 4461–4478, 2006
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This chapter contains sections titled: Cationic/Cationic Processes Cationic/Cationic/Cationic Processes Cationic/Pericyclic Processes Cationic/Reductive Processes
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The cationic surfactants based on biamide and imidagoline quaternary ammonium salts were synthesized and the content of cations was determined. The fatliquor for leather prepared by the above two cationic surfactants was made. The fatliquoring effect of the single cationic fatliquor and compositions one was inspected by the orthogonal design.
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