Polymers ionene

Among the limited examples of polymers originated by path b (Fig. 153), the polymerization- of diallylamino Mannich bases leading to poly(pyrrolidine)s 397 (Fig. 155) is worth mentioning. The synthesis of ionene polymers of the type 398, used in water clarification, by reaaion between /ran.v-l,4-dichloro-2-butene and a phenolic Mannich base,- is also interesting. 

Rembaum et al. [208, 209] have used a displacement reaction to prepare salts of polyamines (called ionene polymers), viz. 

Prepolymerized lipids form vesicles only if the disentanglement of the polymer main chain ( = hack hone) and the membrane forming side-chains is simplified hy a hydrophilic spacer between them . Efficient decouplings of the motions of the polymeric chain and the polymeric bilayer are thus achieved and stable liposomes with diameters of around 500 nm were formed upon ultrasonication (Figure 4.28a). Their bilayer showed a well-defined melting behaviour in DSC. The ionene polymer with C12, C16 and C20 intermediate chains also produced vesicles upon sonication (Figure 4.28b). Here, the amphiphilic main chain is obviously so simple that ordering to form membranes produces no problems whatsoever . ... 

Figure 4.28 a) Disentanglement of the polymer main chain from the membrane surface by hydrophilic spacers, often ethylene glycol oligomers, is the best means to synkinetize vesicles from amphiphilic polymers. Ordering of the amphiphiles must not be disturbed by their covalent connections, b) Folding of the ionene polymer spontaneously yields monolayer vesicle membranes. ... 

Polymers incorportating viologen units in their main chains were also prepared (Figure 6 see Appendix for details of the procedure).46,47 The effects of counterions and additives on the photochromism of viologen ionene polymers... 

Han HS, Bhowmik PK (1995) Liquid-crystalline main-chain ionene polymers. Trends Polym... 

It has been assumed (1A9) that volatilization of the acetic acid occurs during the drying cycle of the urethane latices, which then no longer contain hydrophilic amine acetate groups. Rembaum and coworkers (152-156) also reported the preparation of cationic polyurethanes and various applications of these polymers, which were termed "ionene polymers" because they contained ionic amines. 

Typically, the CDs were shown to form inclusion complexes with some ionic polymers, with both a-CD and /3-CD complexing with ionene polymers, cationic polymers containing a polymethylene chain, and bipyridinium cation groups in aqueous solution (Figure 36.11) [81]. In these cases, the complexes proved to be water-soluble, which enabled spectroscopic methods to be used for their characterization. The NMR spectrum of the polymer in the presence of a-CD demonstrated a splitting of each peak, in addition to two sets of peaks for both methylene protons and aromatic protons this indicated that the polymer had formed a stable complex with a-CD. In contrast, the NMR spectrum showed that all the protons had broadened on the addition of /3-CD this indicated that the polymer had formed dynamic complexes with /S-CD. Notably, y-CD failed to cause any changes in the H NMR spectrum of the polymer. 

Linear as well as cross-linked ionenes are endowed with interesting pharmacological properties. The biological effects of the ionene polymers were investigated and compared with the pharmacological properties of monomeric ammonium salts as well as with existing model compounds [8]. Several systems such as DNA, bacteria, fungi, mammalian cells in culture and laboratory animals were used in these studies. 

Inhibitory concentrations of different ionene polymers on Staphylococcus aureus and Escherichia coli... 

Insolubilized ionene polymers retain their antimicrobial properties. The insolubilization can be achieved either by exchanging the counterions or by an ionic cross-linking reaction [8]. Thus addition of potassium iodide, iodine aqueous solution to an aqueous solution of ionene chloride yields structure II... 

Ionene polymers exhibit toxic effects when injected into mice intraperitoneally (i.p.). The i.p. lethal dose for 50% survival (LD50) is, however, comparable to that of a... 

Toxicity of 3,3 and 6,10 polyionenes to normal WI-38 cells and SV40 WI-38 cells in monolayer cultures was studied by the standard 3-day growth response. Thirty ml Falcon plastic culture flasks were seeded with 0.25 x 10 cells/flask in 5 ml of Eagle s medium -t-10% fetal calf serum. After 24 hours, the medium was replaced with the medium containing different concentrations (0-10 /ig/ml of 3,3 or 6,10 ionene polymer and the cells were allowed to grow for an additional three days. On the fourth day the cells were trypsinized and the number of cells per ml was calculated with the use of a Coulter particle counter. Three replicate flask cultures were analyzed at each concentration and the experiments were repeated twice. The growth factor (GF) for each treatment was calculated as the ratio of the number of cells/ml on day 4 to the number of cells/ml on day 1 (on the day of initiation of the treatments) and was expressed as percent of the control. The toxicity was plotted as a function of concentration as shown in Figures 3 and 4. 

The 3,3 ionene polymer was slightly more toxic to the SV40 WI-38 cells at concentrations up to 4 g/ml but above this concentration the normal WI-38 cells were more sensitive to 3,3 ionene polymer than the SV40 WI-38. The nature of the toxicity response of SV40 WI-38 cells to 3,3 ionene polymer indicates that a fairly large proportion of the transformed cell population was resistant to this compound, while the remainder was very sensitive. However, the transformed cells were extremely sensitive to 6,10 ionene polymer even at the lowest concentration tested (2 /ig/ml).The... 

For similar reasons, we were unsuccessful to synthesize ionene polymers [5] of structure VI, and the reaction of tetramethylamino methane with dibromomethane yielded small molecules instead of VI. Furthermore, the crosslinked resins obtained by the reaction of 4-VP with dihalides contained unreacted bromine end groups. In order to determine the reason for this observation we have investigated the rate of quaternization of a model compound (structure VII) with pyridine. 

Renbaum, A. (1973). Biological activity of ionene polymers. Applied Polymer Symposium, 22, 299-317. 

Catalyst MH-3, prepared from surfactant 6, was more active, and catalyst MH-2, prepared from surfactant 5, was less active than MH-1. We are continuing study of the oxidation kinetics to understand better the mechanism of oxidation. As with soluble poly(vinylamine) and ionene polymers containing CoPcTs, the mechanism does appear to involve Ae thiolate anion, and the rates of reaction are not simply dependent on the first power of CoPcTs concentration. There is evidence for formation of hydrogen peroxide during the CoPcTs-catalyzed autoxidation of mercaptoethanol. 4>5l At this time we do not know if there are significant differences in the mechanisms of autoxidation of mercaptoethanol catalyzed by polyelectrolytes and autoxidation of 1-decanethiol catalyzed by cationic latexes. 

Other chelating polymers related structurally to polyethylenimine and polyethyl-enimine have been derived from cyclopolymerized diallylamines. The structure and properties of these resins have been reviewed by Hodgkin. The attempted synthesis of novel linear poly(lV-alkylethylenimine)s, for metal complexation, by demethylation of ionene polymers has been described.The reaction (involving treatment with UAIH4) was successful only with ionene oligomers. 

It now seems that the chemistry of these reactions is more complicated than originally envisaged. Salamone et al., give reasons for believing that initiation does not involve addition of sulphonate or acrylate anions to (VPH)+ as proposed by Kabanov but is more likely to occur through nucleophilic addition of unquaternized VP. They also find that with strong adds in aqueous solution VP forms either ionene polymers (3) or monomeric vinylpyridinium salts. 

According to Mielke and Ringsdorf, - polymerization of 4-vinylpyridinium salts in aqueous solution may give either the vinyl (1,2) polymer or an ionene polymer according to the conditions free radical polymerization is also possible. Klein favoured a mechanism of the Kabanov type for the spontaneous polymerization of 2-vinylpyridine in the presence of poly(methacrylic acid). 

Polymerization of 4-vinylpyridine on sodium pyrophosphate and isotactic poly(acrylic acid) templates has been reported by Kabanov et al. to yield crystalline complexes containing ionene polymers. 

Ren, S., 2002. Determing the mechanisms of toxic action of phenols to Tetrahymena pyriformis. Environmental Toxicology 17, 119-127 Renbaum, A., 1973. Biological activity of ionene polymers. Applied Polymer Symposium 22, 299-317. 

Noguchi, H., Uchida, Y, Nomura, A., and Mori, S. (1989). A highly lehable humidily sensor using ionene polymers. J. Mater. Sci. Lett. 8 1278. 

When a higher fatty acid as a hydrophobic group was introduced at one or both end(s) (X=RC02 or Nu = RC02) of PMeOZO or PEtOZO of a hydrophilic segment, the products showed excellent surfactant properties.This method seems to be the simplest and economical way for the PROZO surfactants. In addition, a dihalide initiated living POZO and a diamine reacted to afford PROZO ionen polymers. ... 

The electrical conductivity of iodine and TCNQ complexes of a number of types of ionene polymers including those with aromatic rin g incorporated into the ionene backbone have been extensively studied. 

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