Carbohydrate derivatives polyamides

Thiem J., Bachmann F, Carbohydrate-derived polyamides. Trends Polym. Sci., 2,1994, 425-432. 

Bachmann F., Thiem J., Syntheis of hydrophilic carbohydrate-derived polyamides, J. Polym Sci Part A. Polym. Chem, 30,1992,2059-2062. 

Analytical Use of Fluorescence-Producing Reactions of Lipid- and Carbohydrate-Derived Carbonyl Groups with Amine End Groups of Polyamide Powder... 

SYNTHESIS OF CHIRAL POLYAMIDES FROM CARBOHYDRATE-DERIVED MONOMERS... 

Varela O., Orgueira H.A., Synthesis of chiral polyamides from carbohydrate-derived monomers, Adv. Carbohyd. Chem. Biochem.,SS, 1999, 137-174. 

In polymer applications derivatives of oils and fats, such as epoxides, polyols and dimerizations products based on unsaturated fatty acids, are used as plastic additives or components for composites or polymers like polyamides and polyurethanes. In the lubricant sector oleochemically-based fatty acid esters have proved to be powerful alternatives to conventional mineral oil products. For home and personal care applications a wide range of products, such as surfactants, emulsifiers, emollients and waxes, based on vegetable oil derivatives has provided extraordinary performance benefits to the end-customer. Selected products, such as the anionic surfactant fatty alcohol sulfate have been investigated thoroughly with regard to their environmental impact compared with petrochemical based products by life-cycle analysis. Other product examples include carbohydrate-based surfactants as well as oleochemical based emulsifiers, waxes and emollients. 

Similarities in the spectrofluorometric and chemical behavior of the malonaldehyde and Maillard adducts and the constraints of the rather precise geometry of the available amine groups in microcrystalline polyamide are consistent with a possible carbohydrate-substituted amino-iminopropene derivative for the sugar-amine fluorophore. The malonaldehyde product with amino acids and amines has been demonstrated by others to have an amino-iminopropene moiety. 

As already mentioned, there has been renewed interest for using carbohydrates as a source of chemicals since the 1980s with the development of the chemistry of furanic compounds, particularly for the preparation of nonpetroleum derived polymeric materials, such as polyesters, polyamides and polyurethanes.[17,19]... 

It has often been proclaimed that 5-hydroxymethylfurfural (HMF, Fig. 8.35) could be an ideal cross-over compound between carbohydrates and petrochemistry [184], as it is a bifunctional heteroaromatic compound that is accessible from fructose in one step. It was expected that HMF could be developed into a valuable synthetic building block and that its derivatives, such as furan-2,5-dicarb-oxylic acid (FDA), would be able to compete with fossil-derived monomers for use in thermostable polyesters and polyamides. 

Diamino derivatives of carbohydrates have been employed for polycondensation reactions with carboxyl-activated aliphatic and aromatic dicar-boxylic acids. The resulting polyamides are of the AABB type (nylons-m,n analogs), and therefore, the regio- and stereoregularity in the polyamide chain is determined by the configuration of the carbohydrate precursor. When such a molecule lacks a C2 axis of symmetry, random polymerization leads to nonstereoregular polyamides. 

IV. Chiral A,B-Type Polyamides (Nylons-m) Based on Amino Acids Derived from Carbohydrates... 

Just one example of an asparate-type polyamide derived from a carbohydrate precursor poly[isobutyl(25,3R)-3-benzyloxyaspartatc] (133), has... 

Native and microcrystalline cellulose precoated plates are used in the life sciences for the separation of polar compounds (e.g. carbohydrates, carboxylic acids, amino acids, nucleic acid derivatives, phosphates, etc) [85]. These layers are unsuitable for the separation of compounds of low water solubility unless first modified, for example, by acetylation. Several chemically bonded layers have been described for the separation of enantiomers (section 10.5.3). Polyamide and polymeric ion-exchange resins are available in a low performance grade only for the preparation of laboratory-made layers [82]. Polyamide layers are useful for the reversed-phase separation and qualitative analysis of phenols, amino acid derivatives, heterocyclic nitrogen compounds, and carboxylic and sulfonic acids. Ion-exchange layers prepared from poly(ethyleneimine), functionalized poly(styrene-divinylbenzene) and diethylaminoethyl cellulose resins and powders and are used primarily for the separation of inorganic ions and biopolymers. 

Harada A, Saeki K, Takahashi S, Optical resolution of ferrocene derivatives by liquid chromatography using aqueous cyclomaltohexaose as the mobile phase and polyamide as the stationary phase, Carbohydr. Res. 1989 192 1-7. 

The term carbohydrate diacids as used in this report represents that class of compoimds know as aldaric acids, i.e., simple diacids derived from oxidation of the terminal carbons of aldoses. As a class of compounds aldaric acids have been known for more than a century and some of these diacids played an important role in Emil Fischer s assignment of the relative configurations of naturally occurring D-aldoses (1). Surprisingly, these molecules have seen very little chemical application over the past century but their time may have arrived to be considered as valuable and versatile synthons for preparation of specialty chemicals and polyamides. The material in this report presents an overview of... 

We also prepared [101] a series of polyamides (PA- Su) derived from these hexaric acids and non-carbohydrate alkylenediamines with even number of methylenes (n = 4, 6, 8, 10,12). 

Bueno M., Zamora F., Molina 1., Orgueira H.A., Varela O., Galbis J.A., Synthesis and characterization of optically active polyamides derived from carbohydrate-based monomers, J. Polym. Sci Part A Polym. Chem., 35, 1997,3645-3653. 

The primary chemical classes from which adhesives are made include epoxies, acrylics, phenolics, urethanes, natural and synthetic elastomers, amino resins, silicones, polyesters, polyamides, aromatic polyheterocyclics, and the various natural products such as carbohydrates and their derivatives as well as plant- and animal-based proteins. Chemical class was once a relatively clean differentiator of adhesives, but so many adhesives now are hybrids, designed to take advantage of specific attributes of more than one chemical class or type of material. Hybridization can be accomplished by incorporating into an adhesive a nonreactive resin of a different chemical class adding another type of reactive monomer, oligomer,... 

Sebastian Munoz-Guerra completed his Ph.D in Organic Chemistry in 1974 at the University of Seville. After postdoctoral work on crystal structure and morphology of non-conventional nylons, he initiated research on synthesis and characterization of bio-based polymers and copolymers. Since 1987, he is full Professor in Chemical Engineering at the Technical University of Catalonia in Barcelona. His current research is focussed on the development of polyesters, polyamides and polyurethanes derived from carbohydrates with special attention paid to industrial aromatic polyesters, as well as on modification of microbial biopolymers with therapeutic interest. He has authored more than 200 peer reviewed papers and several book chapters, and has been granted more than 15 patents on these issues. 

One initial response of scientists to this challenge was to design new polymers for packaging applications with chemical structures as close as possible to nature s building blocks namely derivatives of carbohydrates, polyamides and polyesters. Examples of this approach are discussed elsewhere in this book... 

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