Water-soluble Polyamide Research Articles

Low Molecular Weight Shuttle Molecules Enhance Polychloramide Antimicrobial Activity.

Investigated were the influences of succinimide (SI), 5,5-dimethylhydantoin (DMH), and 3-(hydroxymethyl)-5,5-dimethylhydantoin (HDMH) on the biocidal activity of chlorinated, water-soluble polyamide prepared by the reaction of isopropylamine with poly(styrene-alt-maleic anhydride). The resulting polymer was a negatively charged, water-soluble polymer bearing a carboxylic acid and an isopropylamide moiety on nearly every repeat unit. Subsequent treatment with NaOCl chlorinated the polymers to up to 4.4% Cl while inflicting some polymer chain scission. SI, DMH, or HDMH increased the biocidal activity of polychloramides toward planktonic Escherichia coli and Staphylococcus aureus. Independent solution studies confirmed that oxidative chlorine spontaneously transferred from aqueous polychloramides to small molecules. We concluded that SI, DMH, and HDMH acted as shuttles that extracted oxidative Cl from the polymer chloramides and transported oxidative Cl more efficiently to microbial surfaces. Succinimide was the most effective shuttle. These results warn that some low molecular weight soluble molecules in antimicrobial testing solutions may exaggerate the effectiveness of the polymer or immobilized antimicrobial agents.

Polyacrylonitrile nanofiber reinforced polyimide composite aerogels with fiber-pore interpenetrating structures for sound absorption, air filtration and thermal insulation

Prolonged noise pollution and its induced vibration would not only lead to the failure of instruments and equipment, but also endanger human health. In this work, with water-soluble polyamide acid (PAA) as the matrix and polyacrylonitrile nanofiber (PANNF) as the reinforcement, PANNF reinforced polyimide (PANNF/PI) composite aerogels with fiber-pore interpenetrating structures are fabricated by the method of “homogeneous mixing, freeze-drying and heat treatment”. PANNF that intersperses among pores can effectively inhibit the shrinkage of PI aerogels and enhance sound absorption and mechanical properties. With PANNF dosage of 10 wt%, the composite aerogels own the excellent sound absorption performance, with noise reduction coefficient (NRC) of 0.398, and average sound absorption coefficient (SAC) of 0.913 in the frequency range of 2000∼6300 Hz. The composite aerogels also have excellent mechanical properties, with Young's modulus of 12.42 kPa, stress loss of 3.64% and energy loss coefficient of 0.203. 10 wt% PANNF/PI composite aerogels also possess satisfying air filtration performance (97.2% filtration efficiency for PM2.5, quality factor (QF) value of 0.0396 Pa-1; and 99.4% filtration efficiency for PM10, QF value of 0.0567 Pa-1) and thermal insulation performance (thermal conductivity coefficient as low as 0.036 W/(m·K)).

Water-Soluble Polyamide Acid Binder with Fast Li+ Transfer Kinetics for Silicon Suboxide Anodes in Lithium-Ion Batteries.

Silicon suboxide (SiOx) anodes have attracted considerable attention owing to their excellent cycling performance and rate capability compared to silicon (Si) anodes. However, SiOx anodes suffer from high volume expansion similar to Si anodes, which has been a challenge in developing suitable commercial binders. In this study, a water-soluble polyamide acid (WS-PAA) binder with ionic bonds was synthesized. The amide bonds inherent in the WS-PAA binder form a stable hydrogen bond with the SiOx anode and provide sufficient mechanical strength for the prepared electrodes. In addition, the ionic bonds introduced by triethylamine (TEA) induce water solubility and new Li+ transport channels to the binder, achieving enhanced electrochemical properties for the resulting SiOx electrodes, such as cycling and rate capability. The SiOx anode with the WS-PAA binder exhibited a high initial capacity of 1004.7 mAh·g-1 at a current density of 0.8 A·g-1 and a capacity retention of 84.9% after 200 cycles. Therefore, WS-PAA is a promising binder for SiOx anodes compared with CMC and SA.

Robust hollow glass microspheres-based solar evaporator with enhanced thermal insulation performance for efficient solar-driven interfacial evaporation

Solar-driven interfacial evaporation is a green and efficient technology with wide applications, such as seawater desalination, wastewater treatment and electrical generation, and so on. Herein, we report a novel composite aerogel (PI-MWCNT-MHGM) using (3-aminopropyl)triethoxysilane modified hollow glass microspheres (MHGM), carboxylated multiwalled carbon nanotubes (MWCNT), and water-soluble polyamide via simple directional freezing and freeze-drying methods for solar-driven interfacial evaporation. Owing to the directional freezing method, the hollow structure of HGM, and strong chemical interactions in PI-MWCNT-MHGM, the PI-MWCNT-MHGM composite aerogel exhibits porous structure with vertically aligned channels, strong mechanical properties, low thermal conductivity, and excellent thermal insulation, as well as broadband light absorption. As expected, the PI-MWCNT-MHGM evaporator shows a high evaporation rate (1.506 kg m−2 h−1) under 1 kW m−2 solar irradiation and excellent salt resistance, e.g., even when 1 g of NaCl was placed on the surface of the PI-MWCNT-MHGM, it could dissolve within 10 min. Moreover, the PI-MWCNT-MHGM possesses self-floating ability, combined with its eco-friendly, facile, and potentially scalable preparation method, the prepared aerogel may hold great potential for real applications.

New Anti-Aging and Anti-Wrinkle Material: Properties and Activities of Nanoparticle Containing Poly(Aspartic Acid) Derivatives

Polymers such as sodium polyacrylate; polysaccharides in starch; polyamino acids, which are the products of alpha-amino acid condensation; and polypeptides are widely used in cosmetics and pharmaceuticals. They are used as viscosity agent, emulsifying agent, and carriers for drug delivery. However, we studied the function of polymers as activity agent, especially that of synthesized poly(aspartic acid). Poly(aspartic acid) is a biocompatible synthetic polymer. It is a water-soluble polyamide containing carboxylic pendants prepared from polysuccinimide, the polycondensate of aspartic acid monomer, by hydrolysis. In this study, we prepared poly(aspartic acid) derivatives conjugated with L-lysine or L-lysine and other materials. The chemical structure of these polymers was confirmed by FT-IR and 1H-NMR spectroscopy. Moreover, these novel poly(aspartic acid) derivatives stimulated typeⅠcollagen biosynthesis and inhibited MMP-1(collagenase) activity. We could conclude that the microfludization process improved skin permeability and confirmed better permeability than that achieved with existing nano emulsions.

Synthesis and characterizations of a series of water soluble polyamides and their micellization behavior

A series of water soluble polyamides were synthesized via melt-polycondensation using glutaric acid and poly(propylene glycol) bis(2-aminopropyl ether) as monomers. The chemical structures of the polyamides were ascertained by FT-IR and 1H NMR. The thermal properties of the polyamides under consideration were measured by TGA and DSC. It was found that one kind of the polyamides can self-assemble into nano-size vesicles with densely packed multilayer wall in aqueous solution, while another polyamide can self-assemble into large complex micelles. Interestingly, these large complex micelles display a unique acid sensitive characteristic according to the TEM and PST measurements.

Synthesis and Characterization of Novel Water-Soluble Polyamides with Enhanced Gas Barrier Properties

Poly(hexamethylene isophthalamide) (PA6I), an amorphous polymer characterized by high temperature resistance and significant oxygen barrier performances, has been chemically modified by using the 5-sulfoisophthalic acid sodium salt as a comonomer. Then, ionic groups have been randomly distributed along the polymeric chains. The new sulfonated PA6I samples were studied in order to understand structure–property relationships. It results that ionomeric PA6Is present an increment of Tg and, accordingly, a decrement of the oxygen transmission rate at 50% of relative humidity with the increment of the ionic content. Ionic groups, indeed, induce the formation of new interactions among the polymer chains, and then, a complex macromolecular network is realized. Interestingly, a molar amount of ionic groups equal to or higher than 10% makes sulfonated polyamides water-soluble. This characteristic, exploited to prepare new coatings on different polymers, opens a range of new applications for ionomeric PA6I.

Synthesis of a novel water-soluble polyamide dendrimer based on a facile convergent method

A novel, rapid, inexpensive, and highly efficient convergent approach has been developed for the synthesis of a 32-amine-terminated G3 polyamide dendrimer by the hydrolysis of the dendrimer with trifluoroacetamide groups. The resulting dendrimer could be successfully modified with oligo(ethylene glycol) chains at its periphery to afford a novel water-soluble polyamide dendrimer. The structural homogeneity of the dendrimers was confirmed by NMR and MALDI-TOF mass spectroscopies.

Synthesis and Proteomic Activity Evaluation of a new Isotope-Coded Affinity Tagging (ICAT) Reagent

During recent years, quantitative proteome profiling has taken advantage of incorporating the traditional stable isotope dilution analysis into global scale or discovery-based proteomic experiments that use mass spectrometers as detectors to allow the pairwise study of differently expressed proteins. Quantitative protein analysis by means of the isotope-coded affinity tag (ICAT) method and tandem mass spectrometry (MS) enables the pairwise comparison of protein expression levels in biological samples. Herein, a modified ICAT reagent, named BAA-ICAT (beta-alanine-arm-ICAT) in which the polyether linker is replaced by a more water-soluble polyamide one, was investigated.

Synthesis and characterization of novel water-soluble polyamide based on spermine and aspartic acid as a potential gene delivery vehicle

We developed a novel and convenient method for the synthesis of a potentially safe non-viral gene delivery vehi- cle based on the cationic block copolymer of spermine and aspartic acid (ASSP) and coupled it with polyethylene glycol (PEG). The copolymer ASSP was prepared by direct polycondensation in the ionic liquid, butylmethylimidazolium hexa- fluorophosphate, using triphenyl phosphite as the condensing agent under mild reaction conditions. The highly hydropho- bic ASSP was transformed into a water soluble hydrophilic micelle by coupling ASSP with polyethylene glycol (PEG) using the same ionic liquid and 1,1-carbonyl diimidazole as the condensing agent without harsh conditions. The polyca- tionic ASSP-PEG was then used to condense calf thymus and plasmid deoxyribonuclceic acids (DNAs) in Tris-HCl buffer (pH 7.4) to get a series of block ionomer complexes with various charge ratios. The physicochemical properties of the copolymer micelle and the DNA polyplexes were studied using fourier transform-infrared (FTIR), nuclear magnetic reso- nance (NMR) and circular dichroism (CD) spectroscopy, matrix assisted laser desorption/ionization-time of flight mass spectrometry (MALDI-TOF MS), differential scanning calorimetry (DSC), transmission electron microscopy (TEM) and particle size measurements. It was observed that the DNA was condensed to compact particles by its interaction with the copolymer. Since DNA condensation to nano/micrometer sized particles is essential for gene delivery, our results indicate a potential use of the copolymer for gene delivery applications.

Matrix polymerization of aniline in the presence of polyamides containing sulfo acid groups

The matrix synthesis of polyaniline in the presence of water-soluble aromatic polyamides containing sulfo acid groups has been studied. It has been shown that the nature of polyacid and the concentration of reagents affect the shape and dynamics of a change in absorption spectra. The S-shaped profile of kinetic curves for spectra variation and the experiments on the seed polymerization provide evidence for the autocatalytic character of polymerization. It has been concluded that, depending on the nature of polyacid, polymer complexes form in which polyaniline macromolecules are situated along main chains of polyacid macromolecules (the two-stream structure) or appear as side chains of polyacid macromolecules (the comb-shape structure). In the latter case, polyaniline macromolecules serve as ionic bridges crosslinking polyacid macromolecules, as is confirmed by the viscometric study of solutions in the course of polymerization.

A Water-Soluble Polyamide Containing cis-dicarboxylato-chelated Platinum(II)

For use as a macromolecular drug carrier in the development of carrier-bound platinum anticancer drugs, the water-soluble polyamides 1 and 2 have been synthesized, meeting the specific structural requirement of the presence of pairs of carboxyl groups directly attached to the polymer main chain in 1,1geometry. The synthesis involves solution polymerization of diamines with the key monomer, 2,2-bis(2-methoxycarbonylethyl)malonic acid (6), prepared from diethyl malonate via several intermediary malonic acid derivatives. The diamine monomers are 1,3-diaminopropane and 4,7,10-trioxa-1,13-tridecanediamine, leading, respectively, to the polyamides 1 and 2. The polymerization proceeds in the presence of anhydrous sodium carbonate. Rigorous purification by precipitation, reprecipitation, and aqueous dialysis, followed by freeze-drying, furnishes the target compounds as water-soluble, solid polymers, which are structurally characterized by spectroscopic and microanalytical techniques. The exemplifying platination of carrier 2 with DACH-Pt (trans-1,2-diaminocyclohexanediaquaplatinum(II) dinitrate) provides the conjugate 2-Pt as a water-soluble compound with a Pt content of 8%.

Solid state polycondensation within cyclodextrin channels leading to watersoluble polyamide rotaxanes

α,ϖ-Aminocarboxylic acids form microcrystalline inclusion compounds with α-cyclodextrin. In these inclusion compounds cyclodextrins build up channel structures, in which the α,ϖ-aminocarboxylic acids can be polycondensed at 200–240°C. As the resulting polyamides are completely covered by cyclodextrin rings they are readily water-soluble. The dissociation of the polymeric inclusion compounds can be prevented by the introduction of bulky substituents within the polymer chain.

Water soluble polyamides as potential drug carriers. IX. Polyaspartamides grafted with amine-terminated poly(ethylene oxide) chains

The synthesis of side-chain-functionalized polyaspartamides as potential carrier polymers for medicinal agents is described. The nucleophilic ring opening in poly-D,L-succinimide, mediated by O,O′-bis(2-aminopropyl)poly(ethylene oxide) (nominal molecular mass is 600) and ethanolamine under carefully controlled experimental conditions leads to the formation of aspartamide polymers bearing hydrosolubilizing hydroxyethyl side groups in addition to variable proportions of poly(ethylene oxide) (PEO) side chains terminated with primary amino groups. The side chain terminals represent functionalities for drug binding, whereas the PEO constituents contribute to overall hydrophilicity and biocompatibility of the carriers and to enhance their biomedical performance by imparting resistance to protein binding and increasing central circulation lifetime. The water-soluble polymeric products are isolated by dialysis (molecular mass cutoff: 25,000) and freeze-drying in typical yields of 40–60%, with inherent viscosities in the range of 10–18 mL g−1. Polymer compositions are determined by 1H NMR spectroscopy and microanalysis. A selected carrier is modified by N-acylation with 4-ferrocenylbutanoic acid as a model drug, giving a ferrocene-containing, water-soluble conjugate, thus demonstrating the accessibility of the terminal amino groups on the PEO side chains to acylating agents and other potential reactants. © 1997 John Wiley & Sons, Inc. J Appl Polym Sci 66: 911–919, 1997

Cis-Diaminedichloroplatinum(II) Complexes Reversibly Linked into the Main Chain of Water-Soluble Polyamides

As a follow-up study to previous work involving the platination of polyamide carriers through metal chelation by side group-incorporated ethylenediamine ligands, the present investigation is concerned with the synthesis of platinum-containing polymers in which the metal-coordinating ethylenediamine segments are components of the main chain. Two chloro groups in cis geometry are attached to each Pt atom as additional ligands, complementing a square-planar cis-diaminedichloroplatinum(II) complex system. The water-soluble polymeric carriers are synthesized by Michael-type addition polymerization, interfacial polymerization, and high-temperature solution polycondensation techniques and are crudely fractionated by stepwise aqueous dialysis, ultimately in tubing with a molecular mass cutoff of 25,000. Carrier platination is brought about by treatment with tetrachloroplatinate(II) anion in aqueous solution, care being taken to exercise strict control of reaction variables and workup conditions in an effort to restrict platination to the given ligands and avoid metal aquation or hydroxylation. The platinum conjugates, with Pt contents ranging from about 11 to 23% by mass, are completely soluble in aqueous media when freshly prepared, although long-term storage at room temperature in the solid state is conducive to gradual loss of solubility. The conjugates are of interest as carcinostatic agents.

Water‐soluble polyamides as potential drug carriers. VIII. Poly(alkylene oxide)‐grafted polyaspartamides bearing ethylenediamine side‐group functions

AbstractIn continuation of previous investigations of aspartamide‐type polymers as drug carriers, polyaspartamides featuring hydrosolubilizing poly(alkylene oxide) side chains in addition to ethylenediamine side‐group functions as potential drug‐binding sites are synthesized from poly‐D,L‐succinimide by successive aminolytic ring‐opening steps. Yields are in the range of 45–55%. Depending on selected feed ratios, the target polymers contain both the poly(alkylene oxide) and the ethylenediamine groups in systematically varied proportions. Compositions are determined microanalytically and from relative band intensities of the 1H‐NMR spectra. The polymers dissolve smoothly and completely in aqueous media and thus fulfill the major design requirement of water solubility. © 1994 John Wiley & Sons, Inc.

Cis-Diaminedichloroplatinum(II) complexes reversibly bound to water-soluble polyaspartamide carriers for chemotherapeutic applications. I. Platinum coordination to preformed, carrier-attached ethylenediamine ligands

Copolyaspartamides3–5, bearing the ethylenediamine (en) ligand as a repetitive side-chain component in addition to various hydrosolubilizing groups, are synthesized from polysuccinimide1 by a two-step aminolytic ring opening reaction. The completely water-soluble polyamides, possessing inherent viscosities of 5–20 ml g−1, are used as polymeric carriers for the “anchoring” of the biomedically important diaminedichloroplatinum(II) coordination complex. Conjugate formation is brought about by treatment of the carriers with the tetrachloroplatinate(II) dianion in aqueous solution at pH 6.0 ± 0.5. The resulting, water-soluble conjugates3-Pt-5-Pt, purified by dialysis (12,000–14,000 molecular mass cutoff) and isolated in the solid state by freeze-drying from aqueous solution, possess platinum contents in the typical range of 15–25%. The metal is bound as acis-dichloro-en-Pt(II) complex to the polymer main chain via a short spacer segment incorporating a biofissionable amide link suitable forin vivo release of the complex. The conjugates are of interest as water-soluble macromolecular platinum coordination compounds for potential use in the chemotherapy of cancerous diseases.

Cosmetic and pharmaceutical compositions containing niosomes and a water-soluble polyamide, and a process for preparing these compositions: Rose Handjani, Alai Ribier, Gu Vanlerberghe, Arlette Zabotto, Jacquelin Griat, Paris, France assigned to L'Oreal

Cosmetic and pharmaceutical compositions containing niosomes and a water-soluble polyamide, and a process for preparing these compositions: Rose Handjani, Alai Ribier, Gu Vanlerberghe, Arlette Zabotto, Jacquelin Griat, Paris, France assigned to L'Oreal

Synthesis of a polymide containing a glucose unit in the main chain

A new type polyamide containing a glucose unit in the main chain has been synthesized by the polymerization of C 1, C 3, C 4 blocked C 6-carboxymethylglucosamine, prepared from chitin. The deblocking procedure gave the water-soluble polyamide, of MW 1.5 × 10 4, which can be regarded as a model for the recognition site of lectin.