Poly(sulphopropylbetaines): 1. Synthesis and characterization

Soto, Victor; Galin, J. C.

doi:10.1016/0032-3861(84)90276-3

Cited by 158 publications

(58 citation statements)

References 22 publications

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“…Here, no particular problems were encountered, though even when alkylating the amines with the less reactive butane sultone. 29,41 High yields were obtained not only for monomers 4, 5 and 8 with the established substitution patterns of N-alkyl-N,N-dimethylammoniopropanesulfonates and -butanesulfonates, but also for the sulfobetaines derived from the sterically more demanding heterocyclic tertiary amines, 2-3 and 6-7. The features of the monomers' 1 H and 13 C NMR spectra (cf.…”

Section: Resultsmentioning

confidence: 96%

“…The polymerisations in trifluoroethanol proceeded smoothly, in agreement with the literature on other sulfobetaine monomers. [28][29][30]41,46,66 The ratio of monomer to the fluorophore-functionalised CTA in the reaction mixtures was varied between 100 : 1 up to 600 : 1, in order to modulate the molar masses, while the ratio between CTA and the azoinitiator was always kept constant as 5 : 1 (Table 1). Under such conditions, the vast majority of the polymer chains were initiated by the "R"-residue of the RAFT agent and consequently labelled by the fluorophore.…”

Section: Resultsmentioning

confidence: 99%

“…The molecular blueprint of the latter offers a number of variables for systematic structural variations (Scheme 1), and subsequently for investigation of the resulting thermo-responsive behaviour. 18 Still, little work on such variations has been reported to date, 22,29,[41][42][43][44][45][46][47][48][49][50][51] and studies to elucidate their effects on the phase behaviour of these poly(methacrylate)s are scarcer still. 22,29,[52][53][54] Even the aqueous-phase behaviour of the basic polymer of 1, denoted herein as P-1, has not been fully established, as the reported data are apparently conflicting.…”

Section: Introductionmentioning

confidence: 99%

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Effect of the zwitterion structure on the thermo-responsive behaviour of poly(sulfobetaine methacrylates)

Hildebrand

Laschewsky

Päch³

et al. 2017

Polym. Chem.

135

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A series of new sulfobetaine methacrylates, including nitrogen-containing saturated heterocycles, was synthesised by systematically varying the substituents of the zwitterionic group. Radical polymerisation via the RAFT (reversible addition-fragmentation chain transfer) method in trifluoroethanol proceeded smoothly and was well controlled, yielding polymers with predictable molar masses. Molar mass analysis and control of the end-group fidelity were facilitated by end-group labeling with a fluorescent dye. The polymers showed distinct thermo-responsive behaviour of the UCST (upper critical solution temperature) type in an aqueous solution, which could not be simply correlated to their molecular structure via an incremental analysis of the hydrophilic and hydrophobic elements incorporated within them. Increasing the spacer length separating the ammonium and the sulfonate groups of the zwitterion moiety from three to four carbons increased the phase transition temperatures markedly, whereas increasing the length of the spacer separating the ammonium group and the carboxylate ester group on the backbone from two to three carbons provoked the opposite effect. Moreover, the phase transition temperatures of the analogous polyzwitterions decreased in the order dimethylammonio > morpholinio > piperidinio alkanesulfonates. In addition to the basic effect of the polymers' precise molecular structure, the concentration and the molar mass dependence of the phase transition temperatures were studied. Furthermore, we investigated the influence of added low molar mass salts on the aqueous-phase behaviour for sodium chloride and sodium bromide as well as sodium and ammonium sulfate. The strong effects evolved in a complex way with the salt concentration. The strength of these effects depended on the nature of the anion added, increasing in the order sulfate < chloride < bromide, thus following the empirical Hofmeister series. In contrast, no significant differences were observed when changing the cation, i.e. when adding sodium or ammonium sulfate.

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Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Effect of the zwitterion structure on the thermo-responsive behaviour of poly(sulfobetaine methacrylates)

Hildebrand

Laschewsky

Päch³

et al. 2017

Polym. Chem.

135

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“…According to the method report by Monroy Soto et al and our previous work [28][29][30], 4-vinylpyridine propylsulfobetaine (4-VPPS) was synthesized by the ring opening reaction of 1,3-PS with 4-VP. 0.11 mol of 1,3-PS was added to a solution of 0.1 mol of 4-VPPS in benzene in the presence of 6 Â 10 À4 mole of 1,3-dinitrobenzene, which was heated at 80°C for 20 h under continuous stirring.…”

Section: Synthesis Of 4-vpps Monomer and P4vppsmentioning

confidence: 99%

“…Clean bare quartz slide was a used as reference. The intensities of the absorption peaks at 228 nm and 258 nm were monitored because they correspond to the p-p Ã transition of the pyridine rings in P4VPPS [29].…”

Section: Characterization Of Multilayer Filmsmentioning

confidence: 99%

Fabrication of free-standing polyelectrolyte multilayer films: A method using polysulfobetaine-containing films as sacrificial layers

Gui

Qian

et al. 2009

Journal of Colloid and Interface Science

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Behaviour of crosslinked and linear poly[1-(3-sulphopropyl)-2-vinyl-pyridinium-betaine] in aqueous salt solutions

1999

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Linear and crosslinked poly[1‐(3‐sulphopropyl)‐2‐vinyl‐pyridinium‐betaine] (PSPV) samples have been prepared by free radical polymerization of the zwitterionic monomer (SPV) in the absence and presence, respectively, of N,N′‐methylene‐bisacrylamide (MBA). The crosslinked xerogel was swollen to equilibrium at ambient temperature in water and in aqueous solutions of KSCN, KBr and KCl having concentrations ([salt]) extending up to 2 mol dm−3. In aqueous salt the degree of swelling exceeded the value in pure water (0.70), the enhancement in swelling being most marked at low values of [salt]. The content of water within hydrogel increased with salt concentration in swelling medium for low values of [salt] but thereafter fell with further increase in [salt]. In contrast, the salt content within swollen hydrogel displayed a continuous increase with increasing [salt]. The partition coefficient expressing concentration of salt in hydrogel relative to that in swelling medium increased sharply with [salt] at low values, but levelled out to values of 0.8–1.2 at higher values of [salt]. The difference in behaviour among the three salts was not dramatic, but indicated that the affinity of salt for the polymer lay generally in the order KSCN>KBr>KCl. This affinity was confirmed by conductometric determinations of the coefficient of selective adsorption of salt to polymer in solutions of linear PSPV. © 1999 Society of Chemical Industry

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Poly(sulphopropylbetaines): 1. Synthesis and characterization

Cited by 158 publications

References 22 publications

Effect of the zwitterion structure on the thermo-responsive behaviour of poly(sulfobetaine methacrylates)

Effect of the zwitterion structure on the thermo-responsive behaviour of poly(sulfobetaine methacrylates)

Fabrication of free-standing polyelectrolyte multilayer films: A method using polysulfobetaine-containing films as sacrificial layers

Behaviour of crosslinked and linear poly[1-(3-sulphopropyl)-2-vinyl-pyridinium-betaine] in aqueous salt solutions

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