Amido-amines

Synthetic pathways have been deliberately aimed at producing megamers. For example, poly(amido amine) dendrimers of different generations have been combined to give well-defined core-shell megamers in which a central, large core dendrimer is surrounded by a well-defined number of smaller dendrimers. 

Improved high-pressure liquid chromatography (HPLC) methods have been developed for the analysis of quaternary salt type corrosion inhibitors in brine waters [400]. However, these methods are not suitable for imidazolines and amido-amines. A method based on fluorescence detection has been described for the quantitative analysis of the imidazoline- and amido-amine-type corrosion inhibitors in both oil field water and crude oil samples by HPLC [1174]. 

An amido-amine (e.g., from the reaction of tetraethylenepentamine with stearic acid) is modified with propylene oxide [792]. The product is dispersed in a polymer matrix such as an acrylic or methacrylic polymer. The inhibitor is slowly released into the surrounding environment, such as in an oil or gas well, to prevent corrosion of metal equipment in the well. 

R. M. Matherly, J. Jiao, J. S. Ryman, and D. J. Blumer. Determination of imidazoline and amido-amine type corrosion inhibitors in both crude oil and produced brine from oilfield production. In Proceedings Volume. 50th Annu NACE Int Corrosion Conf (Corrosion 95) (Orlando, FL, 3/26-3/31), 1995. 

K. Aoi, K. Itoh, and M. Okada, Globular carbohydrate macromolecules sugar balls Synthesis of novel sugar-persubstituted poly(amido amine) dendrimers, Macromolecules, 28 (1995) 5391-5393. 

Lin C, Blaauboer CJ, Timoneda MM, Lok MC, van Steenbergen M, Hennink WE, Zhong Z, Feijen J, Engbersen JF (2008) Bioreducible poly(amido amine)s with oligoamine side chains synthesis, characterization, and structural effects on gene delivery. J Control Release 126 166-174... 

Figure 1.22 A comparison of dimensional length scales (A) for poly(amido-amine) (PAMAM) dendrimers Nc = 3, Nb = 2 (NH3 core) and various biological entities (e.g. proteins, DNA and lipid bilayers)...

A first generation poly(amido amine) dendrimer has been functionalized with three calyx[4]arenes, each carrying a pyrene fluorophore (4) [30]. In acetonitrile solution the emission spectrum shows both the monomer and the excimer emission band, typical of the pyrene chromophore. Upon addition of Al3+ as perchlorate salt, a decrease in the excimer emission and a consequent revival of the monomer emission is observed. This can be interpreted as a change in the dendrimer structure and flexibility upon metal ion complexation that inhibits close proximity of pyrenyl units, thus decreasing the excimer formation probability. 1H NMR studies of dendrimer 4 revealed marked differences upon Al3+ addition only in the chemical shifts of the CH2 protons linked to the central amine group, demonstrating that the metal ion is coordinated by the dendrimer core. MALDI-TOF experiments gave evidence of a 1 1 complex. Similar results have been obtained for In3+, while other cations such as Ag+, Cd2+, and Zn2+ do not affect the luminescence properties of... 

Figure 11.4 Generation 4.5 poly(amido amine) dendrimer having sodium carboxylate terminal groups.

Figure 11.12 Snapshots of the calculated structure of a poly(amido amine) dendrimer at high and low pH. The size was predicted to increase hy 13% upon progression from high to low pH.

Structure of poly(amido amine) (PAMAM) (G2)-poly(propylene oxide)-... 

Opitz AW, Wagner NJ. Structural investigations of poly(amido amine) dendrimers in methanol using molecular dynamics. J Pol3mi Sci Part B Polym Phys 2006 44 3062-3077. 

Figure 13.5 The structure of the G(2)-poly(amido amine) dendrimer.

Figure 13.10 Synthesis of mannose-/glucose-functionalized dendrimers. For dendrimer loading, x + y = 50% loading was used because optimal activity for glycodendrimers with concanavalin A was previously determined to occur at 50% functionalization. Remaining amines from the poly(amido amine) (PAMAM) substrate were capped as alcohols.

The hemocompatibility of poly(amido-amine) polyelectrolyte complexes was recently studied by Xi, Zhang and coworkers [499, 500]. The poly(amido-amine) was based on piperazine and methylene bisacrylamide, and the polyelectrolyte complexes were obtained from the reaction of poly(amido-amine) with alginic acid, carboxymethyl cellulose or poly(methacrylic acid). Complexes of polyamido-amine and alginic acid with a 1 2 ratio gave the best hemocompatibility. Finally, the blood compatibility of polyelectrolyte complexes based on anionic and cationic cellulose derivatives were studied by Ito et al. [338], In vivo, good blood compatibility of complexes formed from quaternary hy-droxyethyl cellulose reacted with carboxymethyl cellulose and cellulose sulfate was observed. 

Kay and Fust postulated the use of epoxy resin for inhibition of composite propellants [335] and as a consequence, epoxy resins were tried for the first time for the inhibition of HTPB-based composite propellants at Thiokol Corporation, USA. Subsequently, use of the amido-amine hardened modified bisphenol-A-based epoxy resin was reported as inhibitor for fluorocarbon-based composite propellants [336]. Epoxy resins are the most versatile resins for bonding applications for a variety of substrates. This is because of the following characteristics. 

The formation of relatively stable species of the type (ArN)3N Mo N = N—MoN(NAr)3], in which further reduction of the N2 moiety is not very favored, can be prevented by the use of larger (ArN)3N triamido ligands. This led to the development of tris(amido)amine ligands... 

Poly(amido-amine)s. Poly(amido-amine)s [42] offer a system to correlate the effect on Cu(II) complex forming ability with the number (n) of methylene groups between aminic nitrogen. The polymers possess the structures of the type shown in (Fig. 18) and compounds with n = 4 fail to form Cu(II)-complexes in aqueous solution. 

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