Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Journal of Polymer Science Part A: Polymer Chemistry

15 May 2001

Volume 39, Issue 10

Pages 1533–1816

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      The tenth anniversary of Suzuki polycondensation (SPC) (pages 1533–1556)

      A. D. Schlüter

      Version of Record online: 26 MAR 2001 | DOI: 10.1002/pola.1130

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      The Pd-catalyzed cross-coupling reaction of aromatic halides and aromatic boronic acids (Suzuki reaction) has been transferred to polymer synthesis. This article provides a brief historical sketch of this development, focusing on synthetic problems encountered during this process and the structures of the polymers obtained, which mostly belong to the hitherto unknown poly(arylene)s.

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    1. Synthesis and characterization of new soluble polyamides containing phthalimide pendent group (pages 1557–1563)

      Der-Jang Liaw, Pei-Nan Hsu, Jao-Jin Chen, Been-Yang Liaw and Chieh-Ying Hwang

      Version of Record online: 26 MAR 2001 | DOI: 10.1002/pola.1131

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      A series of novel polyamides were prepared by the direct polycondensation of 5-phthalimidoisophthalic acid (PIA) and various aromatic diamines. All of the polymer films had a tensile strength and tensile modulus above 81 MPa and 2.0 GPa, respectively. These polyamides showed glass-transition temperatures (Tg's) between 247 and 273 °C (by DSC) and 248 and 337 °C (by a dynamic mechanical analyzer), and their temperatures at 10% weight loss were in the range of 442–530 °C in nitrogen.

    2. Spontaneous alternating copolymerization of isobutoxyallene with 4-phenyl-1,2,4-triazoline-3,5-dione (pages 1564–1571)

      Shin-Ichi Yamamoto, Fumio Sanda and Takeshi Endo

      Version of Record online: 27 MAR 2001 | DOI: 10.1002/pola.1132

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      The spontaneous copolymerization of isobutoxyallene (1) with 4-phenyl-1,2,4-triazoline-3,5-dione (2) was carried out to afford a copolymer with a number-average molecular weight of 5900–10,300. The copolymer consisted of a 2,3-polymerization unit of 1 and a [BOND]N[DOUBLE BOND]N[BOND] polymerization unit of 2, maintaining an alternating character regardless of the monomer feed ratio. The corresponding copolymerization of 1 with 2 in the presence of methanol afforded the adduct of the compounds without the polymer, indicating the generation of a zwitterion of 1 and 2.

    3. Star-shaped fluorescent polypeptides (pages 1572–1583)

      Harm-Anton Klok, Juan Rodríguez Hernández, Stefan Becker and Klaus Müllen

      Version of Record online: 27 MAR 2001 | DOI: 10.1002/pola.1133

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      Two series of novel, water-soluble, star-shaped polypeptides were prepared via the ring-opening polymerization of γ-benzyl-L-glutamate N-carboxyanhydride and ϵ-benzyloxycarbonyl-L-lysine N-carboxyanhydride followed by the removal of the protecting groups. In aqueous solution, the conformation of the peptide arms could be reversibly changed from a random coil into an α helix by the pH being changed.

    4. A study on acrylamide polymerization by anodic contact glow-discharge electrolysis: A novel tool (pages 1584–1588)

      Susanta K. Sengupta, Urvashi Sandhir and Nira Misra

      Version of Record online: 27 MAR 2001 | DOI: 10.1002/pola.1134

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      Anodic contact glow-discharge electrolysis (CGDE) of aqueous solutions, which generates OH/H in high concentrations near the plasma/anolyte interface, polymerizes acrylamide with a charge efficiency at least 1 order of magnitude higher than that achieved by conventional electropolymerization.

    5. Crosslinkable maleimide copolymers for stable NLO properties (pages 1589–1595)

      İ. E. Serhatli, Y. Yagci, E. Hattemer, R. Zentel, E. Schmälzlin, S. Hohenadl, C. Bräuchle and K. Meerholz

      Version of Record online: 27 MAR 2001 | DOI: 10.1002/pola.1135

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      Second-order, nonlinear optical polymers based on epoxy-substituted methylvinylisocyanates and N-substituted maleimides were synthesized and characterized. The photocrosslinking and thermal-crosslinking reactions of copolymers with different chromophore contents were studied. Electrooptic coefficients (r33), measured for crosslinked and noncrosslinked systems, had similar absolute values and relaxation dynamics.

    6. Application of ketenes to well-defined polyester synthesis. III. Living anionic polymerization of ethyl(4-methoxyphenyl)ketene—Development of polyester having masked phenol side chain (pages 1596–1600)

      Atsushi Sudo, Satoshi Uchino and Takeshi Endo

      Version of Record online: 27 MAR 2001 | DOI: 10.1002/pola.1136

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      A novel ketene, ethyl(4-methoxyphenyl)ketene (EMPK), was synthesized and anionically polymerized by butyllithium or lithium allyoxide to give the corresponding polyesters having predictable molecular weights and narrow molecular weight distributions through a living process.

    7. Polyesters by lipase-catalyzed polycondensation of unsaturated and epoxidized long-chain α,ω-dicarboxylic acid methyl esters with diols (pages 1601–1609)

      Siegfried Warwel, Christoph Demes and Georg Steinke

      Version of Record online: 27 MAR 2001 | DOI: 10.1002/pola.1137

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      The lipase-catalyzed polycondensation of symmetrically unsaturated or epoxidized long-chain α,ω-dicarboxylic acid methyl esters with 1,3-propanediol or 1,4-butanediol led to functionalized polyesters with molecular weights of 1900–11,600 g/mol.

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      Helix-sense-selective polymerization of (1-methylpiperidin-4-yl)diphenylmethyl methacrylate by anionic and free-radical catalyses (pages 1610–1614)

      Tamaki Nakano, Kiyoko Ueda and Yoshio Okamoto

      Version of Record online: 28 MAR 2001 | DOI: 10.1002/pola.1138

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      (1-Methylpiperidin-4-yl)diphenylmethyl methacrylate produced an optically active, helical polymer with a highly isotactic configuration by asymmetric anionic polymerization. The optical activity of the polymer was based on the excess helical sense of the main chain. The monomer also afforded an optically active, helical polymer by the radical polymerization of (−)-menthol as a chiral additive.

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    1. Segmented polyethylene oxides: A new class of polyethers prepared via melt transetherification (pages 1615–1628)

      M. Jayakannan and S. Ramakrishnan

      Version of Record online: 28 MAR 2001 | DOI: 10.1002/pola.1139

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      Several segmented polyethylene oxides were prepared by a melt-transetherification process using 1,4-bis(methoxymethyl)-2,3,5,6-tetramethylbenzene and polyethylene glycols (PEGs) of different molecular weights (di-, tri-, and tetraethylene glycols and PEGs of molecular weights 300, 600, 1000, 1500, and 3400) as the monomers. DSC studies suggest that although the glass-transition temperatures (Tg's) saturate with the oligoethylene glycol spacer length rapidly, the melting temperatures and crystallization propensities attain saturation more gradually. This observation could be particularly important in the context of solid polymer–electrolyte applications, where low Tg's and low crystallization tendencies are important.

    2. A novel route to poly(α-hydroxyacrylic acid) derivatives by the hydrolysis of polymers containing 1,3-dioxolan-4-one moiety (pages 1629–1633)

      Toyoharu Miyagawa, Fumio Sanda and Takeshi Endo

      Version of Record online: 29 MAR 2001 | DOI: 10.1002/pola.1140

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      The alkali hydrolysis of poly(2,2-dimethyl-5-methylene-1,3-dioxolan-4-one) [poly(DMDO)] and poly(2,2-dimethyl-5-methylene-1,3-dioxolan-4-one-co-styrene) [poly(DMDO-co-styrene)] was examined. The hydrolysis of poly(DMDO) could be a new synthetic route for poly(α-hydroxyacrylic acid). The styrene unit in the hydrolyzed copolymer hindered the formation of a lactone ring.

    3. Polymerization of styrene with ionic comonomer, nonionic comonomer, or both (pages 1634–1645)

      Xiao-Jun Xu, Kok-Siong Siow, Ming-Keong Wong and Leong-Ming Gan

      Version of Record online: 29 MAR 2001 | DOI: 10.1002/pola.1141

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      Polymerizations of styrene with ionic comonomer, nonionic comonomer, or both in the absence of an emulsifier produced nanosized polystyrene microlatexes with high polymer contents. The controlled addition of monomer(s) to the primary particles formed in an emulsion yielded smaller latex particles of a rather uniform size. The results show that the surface of the latex particles was enriched in the comonomers.

    4. Structures and thermal properties of chitosan-modified poly(methyl methacrylate) (pages 1646–1655)

      Trong-Ming Don, Shih-Chang Hsu and Wen-Yen Chiu

      Version of Record online: 29 MAR 2001 | DOI: 10.1002/pola.1142

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      The emulsion polymerization of methyl methacrylate was undertaken in the presence of chitosan with potassium persulfate as an initiator. Chitosan not only took part in the polymerization but also served as a surfactant, providing stability for the latex particles. The surface charge of the latex particles in an acid solution was positive and increased with the amount of chitosan. As a result, the isoelectric point also increased with the amount of chitosan. The final particles consisted of poly(methyl methacrylate) (PMMA) homopolymer and chitosan–PMMA copolymer. The presence of rigid chitosan increased the glass-transition temperature of the final latex polymers.

    5. Quantitative analysis of the temperature effect on the radiation crosslinking and scission of polyethylene macromolecules (pages 1656–1661)

      Alexander Shyichuk, Irena Shyichuk, Guozhong Wu and Yosuke Katsumura

      Version of Record online: 30 MAR 2001 | DOI: 10.1002/pola.1143

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      The γ-radiation-induced crosslinking of low-density polyethylene over a wide temperature range was studied with a new log–logarithmic scale method for sol–gel analysis. A straight line was always obtained for the plotting of log (sol fraction) against log (dose). Gel points were accurately obtained from the plot intersects, and scission/crosslinking ratios were obtained from the plot slopes via computer simulations with GelSim6 software. The crosslinking and scission yields were determined to be 0.17 and 0.078 mmol/kJ, respectively, at 30 °C, and they increased to 2.3 and 4.4 mmol/kJ, respectively, at 300 °C. The observed regularities are explained by the fact that enhanced macromolecular motion decreases the cage effect on recombination reactions in the polymer.

    6. Preparing organosoluble aromatic polyimides based on 3,3′,5,5′-tetrabromo-2,2-bis[4-(4-aminophenoxy)phenyl]propane and aromatic dianhydrides (pages 1662–1674)

      Kuo-Yuan Hung and Raymond Chien-Chao Tsiang

      Version of Record online: 30 MAR 2001 | DOI: 10.1002/pola.1144

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      Novel aromatic polyimides were synthesized with a one-step or two-step polymerization process using a bromine-containing diamine and various aromatic dianhydrides. These polyimides were amorphous and readily soluble in many organic solvents.

    7. Cationic grafting of olefins from PVC: The effect of reaction conditions (pages 1675–1680)

      Zhengjie Pi and J. P. Kennedy

      Version of Record online: 30 MAR 2001 | DOI: 10.1002/pola.1145

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      The cationic grafting of isobutylene, styrene, α-methylstyrene, and β-pinene from a poly(vinyl chloride) (PVC) backbone was investigated by using Et2AlCl in solution in the 25 to −70 °C range. The effects of temperature and proton trap [2,6-di-tert-butylpyridine (DtBP)] on grafting-from efficiency (Geff), extent of grafting, branch length, and number of branches per PVC were determined. Reducing the temperature increased the Geff and the molecular weight of branches attached to PVC. By increasing the DtBP concentration, Geff increased; however, the number-average molecular weight of the grafted branches decreased. The lengths of the grafted branches can be controlled, and Geff's close to 100% were obtained.

    8. Main kinetic features of ethylene polymerization reactions with heterogeneous Ziegler–Natta catalysts in the light of a multicenter reaction mechanism (pages 1681–1695)

      Yury V. Kissin

      Version of Record online: 30 MAR 2001 | DOI: 10.1002/pola.1146

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      Several previously known features of ethylene polymerization and copolymerization reactions with heterogeneous, Ti-based Ziegler–Natta catalysts are discussed on the basis of the multicenter polymerization mechanism. Each type of center produces a polymer material (a Flory component) with a uniform structure (copolymer composition, isotacticity, etc.) and a narrow molecular weight distribution (weight-average molecular weight/number-average molecular weight = 2.0). The subjects include temperature and cocatalyst effects on the polymerization kinetics and molecular weight distribution of polymers and reaction parameter effects (temperature, ethylene and hydrogen partial pressures, and α-olefin and cocatalyst concentrations) on the molecular weight of Flory components.

    9. Copper(I)-mediated radical polymerization of methacrylates in aqueous solution (pages 1696–1707)

      Sébastien Perrier, Steven P. Armes, X. S. Wang, F. Malet and David M. Haddleton

      Version of Record online: 4 APR 2001 | DOI: 10.1002/pola.1147

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      α-Methoxypolyethylene oxide methacrylate was polymerized by copper(I)-mediated living radical polymerization in aqueous solution to give polymers with controlled number-average molecular masses and narrow polydispersities. Under appropriate conditions, the reaction reached 50% after 5 h with the polymer having both a number-average molecular weight (Mn) close to the theoretical value and a narrow polydispersity of PDi = 1.15. Optimum results were obtained with the ratios of [Cu(I)]/[Cu(II)] = 10/90 and [Cu]/[2] = 1/1, giving a conversion of 100% after less than 20 h leading to a product having Mn = 8500 and PDi = 1.15. Decreasing the amount of Cu(II) relative to Cu(I) to [Cu(I)]/[Cu(II)] = 0.5/0.5 (maintaining the overall amount of copper) led to 100% conversion after 75 min: Mn = 9500, PDi = 1.10. Block copolymers were demonstrated by sequential monomer addition with good control over Mn and PDi.

    10. Enhanced dissolution of copolymers bearing photobase- or photoacid-generating groups in polar solvents by photochemical formation of ionic pairs (pages 1708–1715)

      Kanji Suyama, Shizue Yamaguchi, Masamitsu Shirai and Masahiro Tsunooka

      Version of Record online: 2 APR 2001 | DOI: 10.1002/pola.1148

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      Solubility changes in the irradiation of copolymers bearing photoacid- or photobase-generating groups and low molecular weight photobase generators (PBGs) or photoacid generators (PAGs) were investigated. Copolymers bearing acyloxyimino (AOI) groups were used as those bearing pendant amino groups photochemically. Copolymers bearing o-nitrobenzyloxycarbonyl and imino sulfonate groups were used as those generating carboxyl and sulfonic groups, respectively. The solubility of copolymers bearing AOI groups into polar solvents after irradiation was enhanced by added PAGs. Similar enhancement was observed in copolymers bearing o-nitrobenzyloxycarbonyl groups in the presence of PBGs. These results showed that the formation of acid–base pairs on irradition was effective for dissolution into polar solvents.

    11. Triphenylphosphine oxide-based bismaleimide and poly(bismaleimide): Synthesis, characterization, and properties (pages 1716–1725)

      Ying Ling Liu, Yuan Ling Liu, Ru Jong Jeng and Yie-Shun Chiu

      Version of Record online: 2 APR 2001 | DOI: 10.1002/pola.1149

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      A novel phosphorus-containing bismaleimide, 3,3′-bis(maleimidophenyl)phenylphosphine oxide (BMPPPO), was synthesized and characterized to exhibit good solubility in common organic solvents; it possessed a low melting point (Tm = 148 °C), a relatively low polymerization temperature (Tp = 214 °C), and a wide processing window (TpTm = 66 °C). Incorporating BMPPPO into poly(bismaleimide) enhanced the polymer glass-transition temperatures, thermal stability, and flame retardancy.

    12. Promoted random orientation of the phenyl substituent of phenylhydroquinone–terephthalic acid polyesters prepared with a diphenyl chlorophosphate/pyridine condensing agent (pages 1726–1732)

      Fukuji Higashi, Mamoru Watabiki and Ji-Hong Kim

      Version of Record online: 2 APR 2001 | DOI: 10.1002/pola.1150

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      The reaction of sterically hindered hydroxyl groups at the 2-position of methylhydroquinone and phenylhydroquinone (PhHQ) to form esters was largely promoted by their slow addition to dicarboxylic acids activated by diphenyl chlorophosphate in pyridine, producing thermotropic terephthalic acid/PhHQ and 2,5-dichloroterephthalic acid/PhHQ polymers with randomly oriented phenyl substituents. Their molecular structures were examined by 13C NMR, and their properties were studied in terms of their transition temperatures, which were determined by differential scanning calorimetry and microscopic observation.

    13. Polyurethanes containing sulfur. III. New thermoplastic HDI-based segmented polyurethanes with diphenylmethane unit in their structure (pages 1733–1742)

      Anna Kultys and Stanisław Pikus

      Version of Record online: 4 APR 2001 | DOI: 10.1002/pola.1151

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      New thermoplastic, high molecular weight, segmented thiopolyurethanes were synthesized from newly obtained aliphatic–aromatic thiodiols as chain extenders, hexamethylene diisocyanate, and 20–80 mol % poly(oxytetramethylene) glycol (PTMG; number-average molecular weight = 1000) as the soft segment by a one-step melt polymerization. The polymers based on 40–80 mol % PTMG were elastomers with low glass-transition temperatures (−60 to −70 °C). Because their structures incorporated diphenylmethane units with active methylene groups, these segmented thiopolyurethanes were potentially peroxide-curable, hexamethylene diisocyanate-based polyurethanes.

    14. Synthesis and characterization of liquid–crystalline polyesters with chiral and achiral twin spacers (pages 1743–1752)

      Rukmani Srinivasan and Ganga Radhakrishnan

      Version of Record online: 3 APR 2001 | DOI: 10.1002/pola.1152

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      Polycondensations in 4,4′-biphenol solution as the mesogenic diol with aliphatic diols HO[BOND](CH2)n[BOND]OH (n = 0, 2–10) as the achiral spacers and L(+)-tartaric acid as the chiral spacer were effected. Investigations of the liquid–crystalline properties of the synthesized copolyesters revealed interesting chiral-phase, polymorphism, and alternation effects of the achiral spacers. The specific rotation measurements showed residual retention of the optical activity.

    15. Copolymerization with depropagation: A study of α-methyl styrene/methyl methacrylate in solution at elevated temperatures (pages 1753–1763)

      D. E. Palmer, N. T. McManus and A. Penlidis

      Version of Record online: 3 APR 2001 | DOI: 10.1002/pola.1153

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      In free-radical polymerization, solvents are routinely used to reduce the solution viscosity and molecular weight. In the case of the α-methyl styrene/methyl methacrylate (α-MS/MMA) copolymer system, reducing the monomer concentration also has significant effects on the copolymer composition and maximum conversion obtained. Reactivity-ratio studies as well as full-conversion-range data were provided, and the results were compared to similar data in the bulk phase from our earlier work. A 30 wt % toluene solution was used for all experimental conditions. Copolymer composition modeling results were also presented.

    16. Synthesis and photochemical property of polymers with pendant donor–acceptor-type norbornadiene moieties (pages 1764–1773)

      Naoyuki Kawashima, Atsushi Kameyama, Tadatomi Nishikubo and Takabumi Nagai

      Version of Record online: 4 APR 2001 | DOI: 10.1002/pola.1154

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      Polystyrene derivatives containing pendant donor–acceptor-type norbornadiene moieties were synthesized with a 100% degree of substitution by the reaction of poly[p-(chloromethyl)styrene] and 1,4,5,6-tetramethyl-3-phenyl-2,5-norbornadiene-2-carboxylic acid or 1,4,5,6,7-pentamethyl-3-phenyl-2,5-norbornadiene-2-carboxylic acid with 1,8-diazabicyclo[5.4.0]undecene-7 as a base. A poly(vinyl ether) derivative containing pendant donor–acceptor-type norbornadiene moieties also was prepared in this way. The photochemical valence isomerization of all the polymers proceeded smoothly with UV irradiation in tetrahydrofuran and in the film state. The rate of the photochemical reaction of the polymers increased efficiently with the addition of 4,4′-bis(diethylamino)benzophenone as a photosensitizer.

    17. Effect of the solvent polarity on the living ligated anionic polymerization of tert-butyl methacrylate and copolymerization with methyl methacrylate (pages 1774–1785)

      C. Zune, C. Archambeau, Ph. Dubois and R. Jérôme

      Version of Record online: 4 APR 2001 | DOI: 10.1002/pola.1155

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      An anionic polymerization of t-butyl methacrylate and a copolymerization with methyl methacrylate were initiated with an organolithium ligated with 10 equiv of LiCl. As a rule, the complexation of the active species by LiCl masked the effect that the polarity of the solvent might have on the molecular structure of the chains.

    18. Synthesis and properties of new organosoluble and alternating aromatic poly(ester-amide-imide)s with pendant phosphorus groups (pages 1786–1799)

      Guey-Sheng Liou and Sheng-Huei Hsiao

      Version of Record online: 4 APR 2001 | DOI: 10.1002/pola.1156

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      Two novel series of phosphorus-containing aromatic poly(ester-amide-imide)s with good solubility and thermal stability were prepared via low-temperature solution polycondensation from diesteramines [1,4-bis(4-aminobenzoyloxy)-2-(6-oxido-6H-dibenz〈c,e〉〈1,2〉oxaphosphorin- 6-yl)naphthalene (p-3) and 1,4-bis(3-aminobenzoyloxy)-2-(6-oxido-6H-dibenz〈c,e〉〈1,2〉oxaphosphorin-6-yl)naphthalene (m-3)] with three imide ring-preformed diacid chlorides. Transparent, tough, and flexible films of these polymers were cast from N,N-dimethylacetamide or N-methyl-2-pyrrolidone solutions. The limiting oxygen indices of these polymers were 41–46.

    19. Synthesis and characterization of novel polyimides bearing a side chain composed of stilbene mesogen and undecyl spacer and the alignment ability of nematic liquid-crystal molecules (pages 1800–1809)

      J. H. Park, B.-H. Sohn, J. C. Jung, S. W. Lee and M. Ree

      Version of Record online: 4 APR 2001 | DOI: 10.1002/pola.1157

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      Four different polyimides with side chains containing undecyl spacers and 4-fluorostilbene mesogen end groups were prepared, and their structures and the controllability of the liquid-crystal (LC) alignment with rubbing were investigated. From X-ray scattering and differential scanning calorimetry data, PMDA-, BTDA-, and ODPA-based polyimides were shown to have layered structures and short-range ordering. Pretilt angles of LCs on the rubbed surfaces were 1–9°, depending on the rubbing density and backbone. In particular, the long undecyl spacers caused the mesogenic stilbene end groups to lie next to the main chain, resulting in a reduction in the pretilt angles.

    20. Preparation of antimicrobial sodium alginate with chito-oligosaccharide side chains (pages 1810–1816)

      Jae Wook Song, Han Do Ghim, Jin Hyun Choi, Sohk-Won Ko and Won Seok Lyoo

      Version of Record online: 4 APR 2001 | DOI: 10.1002/pola.1158

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      We reacted chito-oligosaccharide (COS) with N-methylol acrylamide (NMA) with N-methylol groups to prepare acrylamidomethyl chito-oligosaccharide (COS–NMA). Sodium alginate (SA) with COS side chains (SA–COS) was produced through a subsequent reaction of SA with COS–NMA. With a two-step method, we successfully prevented insoluble-complex formation due to electrostatic attraction between chitosan and alginate. SA–COS showed excellent antimicrobial activity, with the growth of microorganisms completely suppressed by a small amount of COS (1.8 wt %).

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