Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Vol. 50 Issue 23

1 December 2012

Volume 50, Issue 23

Pages i–iv, 4805–4994

  1. Cover Image

    1. Top of page
    2. Cover Image
    3. Rapid Communication
    4. Articles
    5. Notes
    1. You have free access to this content
      Cover Image, Volume 50, Issue 23 (pages i–ii)

      Article first published online: 26 OCT 2012 | DOI: 10.1002/pola.26427

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      A number of important aspects regarding recycling post-consumer plastic into valuable, materials are portrayed in the image, and presented by Frank A. Leibfarth, Nicholas, Moreno, Alex P. Hawker and Justin D. Shand on page 4814. The chemical structures in, the forefront emphasize the importance of molecular-level control over the recycling, process. Scattered throughout are representations of the numerous consumer products, that can be recycled using this process: the water bottle, a coffee cup, utensils, vegetable/fruit packaging, etc. A stopwatch indicates the speed and efficiency of the chemistry, while the dollar signs on the ground below are meant to emphasize the valuable materials, made from this commodity plastic. Finally, the oil drums and barrel of PET plastic, signify the energy intensive and inefficient process of the current recycling infrastructure.

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      Inside Cover, Volume 50, Issue 23 (pages iii–iv)

      Article first published online: 26 OCT 2012 | DOI: 10.1002/pola.26428

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      The cover image represents novel amide-linked bisphosphonate-containing dental materials synthesized for improved hydrolytic stability and hydroxyapatite interaction, reported on page 4854 by Burcin Akgun and Duygu Avci. In the work, four (bis)methacrylamide dental monomers containing a bisphosphonate or a bisphosphonic acid functional group are synthesized. The bisphosphonate-containing bismethacrylamide shows potential to be used as a biocompatible crosslinker and the bisphosphonic acidcontaining (bis)methacrylamides as self-etching adhesive monomers.

  2. Rapid Communication

    1. Top of page
    2. Cover Image
    3. Rapid Communication
    4. Articles
    5. Notes
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      A simple modification makes a big improvement to ziegler-natta catalyst (pages 4805–4808)

      He-Xin Zhang, Hao Zhang, Chun-Yu Zhang, Chen-Xi Bai and Xue-Quan Zhang

      Article first published online: 17 AUG 2012 | DOI: 10.1002/pola.26307

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      Since the discovery of the Ziegler-Natta catalyst, many researchers have devoted much effort to improve the catalyst performance. This work reports a simple method to improve the Ziegler-Natta catalyst performance, including catalytic activity, molecular weight, etc. The highest catalyst activity of modified catalyst is more than 3 times higher than that of the corresponding commercial Ziegler-Natta catalyst.

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      Use of Gd powder as catalyst for single electron transfer-living radical polymerization: Applications for synthesis of high molecular weight polymethyl methacrylate (pages 4809–4813)

      Delong Liu, Hou Chen, Ping yin, Zhihai Hao and Lijun Fan

      Article first published online: 24 AUG 2012 | DOI: 10.1002/pola.26310

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      Well-defined PMMA was synthesized by SET-LRP with Gd(0) powder as novel catalyst. The polymerizations proceed in the features of controlled/living polymerization as evidenced by first-order kinetic plots of polymerization, the linear increase of molecular weight values with monomer conversions, and narrow PDI values of the polymers. The apparent activation energy of polymerization is calculated to be 38.8 kJ/mol.

  3. Articles

    1. Top of page
    2. Cover Image
    3. Rapid Communication
    4. Articles
    5. Notes
    1. Transforming polylactide into value-added materials (pages 4814–4822)

      Frank A. Leibfarth, Nicholas Moreno, Alex P. Hawker and Justin D. Shand

      Article first published online: 20 AUG 2012 | DOI: 10.1002/pola.26303

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      Post-consumer bioplastics can be recycled to yield industrially valuable small molecules commonly employed as cosmetics, fragrances, food additives, and plasticizers. The strategy uses an organic catalyst and quantitatively transforms waste plastics into these valuable chemicals in under ten minutes at room temperature. This work contributes to the ultimate goal of reducing further reliance on petrochemical feedstocks.

    2. Investigation on thermoresponsive behavior of biodegradable poly(γ-glutamic acid)-graft-L-phenylalanine ethyl ester (pages 4823–4828)

      Amornrat Lertworasirikul, Nu-orn Choothong, Hiroaki Yoshida, Michiya Matsusaki, Toshiyuki Kida, Apirat Laobuthee and Mitsuru Akashi

      Article first published online: 20 AUG 2012 | DOI: 10.1002/pola.26309

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      A novel thermoresponsive polymer based on poly(γ-glutamic acid), a naturally occurring poly(amino acid), was reported. Poly(γ-glutamic acid)-graft-L-phenylalanine ethyl ester is a biodegradable, biocompatible, and non-toxic material. The copolymer can self-aggregate in aqueous and NaCl solutions. The clouding temperature (TC) can be varied by changing the grafting degree of the copolymer, type of solvent, and/or polymer concentration. Reversible thermoresponsive behavior was observed.

    3. Effect of branched alkyl chains attached at sp3 silicon of donor–acceptor copolymers on their morphology and photovoltaic properties (pages 4829–4839)

      Tatsuaki Nakanishi, Yasuhiro Shirai, Takeshi Yasuda and Liyuan Han

      Article first published online: 24 AUG 2012 | DOI: 10.1002/pola.26315

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      The degree of π–π interactions is studied in two copolymers composed of 2-octylbenzotriazole and dialkyldithienosiloles with linear hexyl (P1) and branched 2-ethylhexyl groups (P2). Although the branched ethyl group can be positioned above the π-plane of dithienosilole to bring disadvantage to stacking among the polymers, the solid-state absorption spectra of the polymers reveal that P2 possesses stronger interchain interactions than P1. The photovoltaic properties of each polymer are evaluated with [6,6]-phenyl-C71-butyric acid methyl ester.

    4. Protective encapsulation of acid-sensitive catalysts using polyethylene ligands (pages 4840–4846)

      Jakkrit Suriboot, Christopher E. Hobbs, Yun-Chin Yang and David E. Bergbreiter

      Article first published online: 20 AUG 2012 | DOI: 10.1002/pola.26319

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      Metal salen complexes that attached to the termini of polyethylene oligomers are useful catalysts when in solution at elevated temperature. However, when in the form of solid precipitates, these complexes are encapsulated in a hydrocarbon matrix and like reactive species dispersed and stabilized in paraffin wax in this state, they are protected from external acids that could adventitiously demetalate these complexes during a reaction workup.

    5. A Solution-processible, n-dopable polypyrrole derivative (pages 4847–4853)

      Pinar Camurlu, Esin Eren and Cemil Gültekin

      Article first published online: 28 AUG 2012 | DOI: 10.1002/pola.26321

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      The synthesis of a soluble, ambipolar, florescent, electrochromic polypyrrole (PPyNI) derivative that was achieved through both chemical and electrochemical polymerization of 2-[6-(1H-pyrrol-1-yl)hexyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione (PyNI) is presented. Electrochromic properties of the polymer were investigated by spectroelectrochemistry, kinetic, and coloration efficiency studies and colorimetry measurements. Moreover, an electrochromic device based on PPyNI and poly(3,4-ethylenedioxythiophene) was constructed and characterized.

    6. Synthesis and evaluations of bisphosphonate-containing monomers for dental materials (pages 4854–4863)

      Burcin Akgun and Duygu Avci

      Article first published online: 20 AUG 2012 | DOI: 10.1002/pola.26305

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      Two new bismethacrylamide and two new methacrylamide dental monomers, in each group one monomer containing a bisphosphonate and the other a bisphosphonic acid functional group, were synthesized. The bisphosphonate-containing bismethacrylamide shows potential to be used as a biocompatible crosslinker due to its copolymerizability with dental monomers such as Bis-GMA and HEMA. The bisphosphonic acid-containing (bis)methacrylamides exhibit a great potential to be used as self-etching adhesive monomers due to their etching ability, hydrolytic stability, and copolymerizability with dental monomers such as HEMA.

    7. Oxidative polymerization of 2,6-dimethylphenol to form poly(2,6-dimethyl-1,4-phenylene oxide) in water through one water-soluble copper(II) complex of a zwitterionic calix[4]arene (pages 4864–4870)

      Li-Min Wan, Hong-Xi Li, Wei Zhao, Hong-Ye Ding, Yang-Yang Fang, Pei-Hong Ni and Jian-Ping Lang

      Article first published online: 17 AUG 2012 | DOI: 10.1002/pola.26308

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      A mononuclear copper(II) cationic catalyst [Cu(II)L(H2O)]I2 with a wine-shaped structure was prepared from reactions of Cu(OAc)2·H2O with ammonium calix[4]arene [H4L]I4 in methanol and water. This complex could initiate the oxidative polymerization of 2,6-dimethylphenol in H2O at 70 °C to produce relatively high-molecular-weight poly(2,6-dimethyl-1,4-phenylene oxide) polymers with narrow molecular weight distributions (Mw/Mn = 1.2–1.5) in good yields.

    8. Synthesis of crosslinked poly(butyl methacrylate-co-pentaerythritol triacrylate) gel by single electron transfer-living radical polymerization and its oil-absorbing properties (pages 4871–4878)

      Lijun Fan, Hou Chen, Zhihai Hao and Zhi Tan

      Article first published online: 24 AUG 2012 | DOI: 10.1002/pola.26312

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      A novel high oil-absorbing crosslinked gel was synthesized by copolymerization of BMA with a small amount of PETA crosslinker using SET-LRP initiated with CCl4 and catalyzed by Cu(0)/HMTA in DMF. The polymerization followed first-order kinetics as indicated by linear increase of monomer concentration with reaction time. The oil absorptions of the crosslinked gel to chloroform and toluene could reach 51.9 and 34.5 g/g, respectively.

    9. Aqueous reversible addition-fragmentation chain transfer dispersion polymerization of thermoresponsive diblock copolymer assemblies: Temperature directed morphology transformations (pages 4879–4887)

      Stefanie Kessel, Nghia P. Truong, Zhongfan Jia and Michael J. Monteiro

      Article first published online: 20 AUG 2012 | DOI: 10.1002/pola.26313

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      In this study, the formation of various 3D structures formed by a structural reorganization is demonstrated; a process not governed by self-assembly. First, well-defined diblocks, thermoresponsive poly(N-isopropylacrylamide-b-styrene) or P(NIPAM-b-STY), are packaged into spherical particles made in situ using a RAFT nanoreactor technique in water at high concentrations. The resultant spheres reorganized through a temperature stimulus to form the spherical, cylinder, vesicle, loops, buckled spheres, and cauliflower structures.

    10. Synthesis of stable aqueous dispersion of graphene/polyaniline composite mediated by polystyrene sulfonic acid (pages 4888–4894)

      Jing Luo, Sisi Jiang, Yong Wu, Meiling Chen and Xiaoya Liu

      Article first published online: 17 AUG 2012 | DOI: 10.1002/pola.26316

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      A simple procedure is reported for the synthesis of water-dispersible graphene/PANI composite which involves the in situ polymerization of aniline on the surface of graphene using polystyrene sulfonic acid (PSS) as stabilizer and dopant. The obtained graphene/PANI composite is readily dispersible in water and the resulting graphene/PANI composite aqueous dispersion is stable for several weeks without any aggregation or precipitation.

    11. Anti-AIDS active polyrotaxane-AZT conjugates with bioactive bulky stoppers and their nanoparticles (pages 4895–4901)

      Sungmo Jung, B. Yerri Swamy, Jin-Bok Moon, Dong-Hyun Kim and Ildoo Chung

      Article first published online: 24 AUG 2012 | DOI: 10.1002/pola.26317

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      Anti-AIDS active polyrotaxane-AZT conjugates with various bioactive bulky stoppers, AZT and tocopherol and their nanoparticles were synthesized for the first time, and showed more potent inhibitors than free AZT, with reduced cytotoxicities against uninfected MT-4 cells. The effect of the conjugates against HIV-1 and HIV-2 strains increased with decreasing particle size.

    12. Functional micropatterned surfaces prepared by simultaneous UV-lithography and surface segregation of fluorinated copolymers (pages 4902–4910)

      Marta Palacios-Cuesta, Marta Liras, Christine Labrugère, Juan Rodríguez-Hernández and Olga García

      Article first published online: 24 AUG 2012 | DOI: 10.1002/pola.26318

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      A new procedure is presented based on the design and preparation of structured and functional surfaces by combination of two approaches simultaneously developed: UV-light lithography to create a surface pattern and surface segregation of a fluorinated copolymer incorporated in the photopolymerizable mixture to modify the surface composition. As a consequence the wettability of the films can be modified depending on the pattern and composition of the blend.

    13. A novel poly(p-phenylene) containing alternating poly(perfluorooctylethyl acrylate-co-methyl methacrylate) and polystyrene grafts by combination of atom transfer radical polymerization and Suzuki coupling processes (pages 4911–4919)

      Yasemin Yuksel Durmaz, Elif L. Sahkulubey, Yusuf Yagci, Elisa Martinelli and Giancarlo Galli

      Article first published online: 17 AUG 2012 | DOI: 10.1002/pola.26320

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      A poly(p-phenylene) (PP), carrying perfectly alternating, well-defined poly(perfluorooctylethyl acrylate-co-methyl methacrylate) (P(FEA-co-MMA)) and polystyrene (PS) side chain grafts, was synthesized by the combination of atom transfer radical polymerization (ATRP) and Suzuki cross-coupling processes. The obtained fluorinated PP showed high static contact angles with interrogating liquids, exhibiting simultaneously hydrophobic (θw = 111°) and lipophobic (θh = 67°) properties.

    14. Controlled radical polymerization of N-acryloylglycinamide and UCST-type phase transition of the polymers (pages 4920–4928)

      Fangyao Liu, Jan Seuring and Seema Agarwal

      Article first published online: 20 AUG 2012 | DOI: 10.1002/pola.26322

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      Controlled (reversible addition fragmentation transfer) polymerization of N-acryloylglycinamide is shown in this work without sacrificing its key property, the upper critical solution temperature in water. The influence of molar mass, polymer end groups, and salt concentration on the cloud point is analyzed by turbidimetry. When nonionic initiators and chain-transfer agents are used, the polymers show a UCST-type phase transition in pure water as well as under physiological conditions.

    15. The effect of molecular weight and catalyst concentration on catalytic activity in mechanochemically activated transesterification using silver(I)-N-heterocyclic carbene latent catalysts (pages 4929–4935)

      Ramon Groote, Lennart van Haandel and Rint P. Sijbesma

      Article first published online: 29 AUG 2012 | DOI: 10.1002/pola.26323

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      The concentration dependence of the activity of polymer-functionalized silver(I)-N-heterocyclic carbene catalysts in ultrasonically activated transesterification reactions was investigated. Potential factors (chemical, mechanochemical, and sonochemical) were systematically addressed, and it was shown that catalyst deactivation by thermal impurities formed during the sonication process results in low mechanocatalytic activity at low catalyst concentrations. Mechanocatalyst activity was strongly enhanced by using higher concentrations of catalyst with higher molecular weights.

    16. Synthesis of well-defined chitosan-based tricomponent copolymers for constructing multifunctional delivery systems (pages 4936–4946)

      Lin Yu, Moyuan Cao, Haiwen Zhang, Han Xiong, Yucun Jin, Yi Lu, Haiyan Jia, Dongsheng Luo, Liqun Wang and Hongliang Jiang

      Article first published online: 29 AUG 2012 | DOI: 10.1002/pola.26324

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      Chitosan-based tricomponent copolymer is synthesized by combining conventional coupling chemistry, SET-LRP, and click reaction for constructing multifunctional micelles with the advantages of wide range of PEG surface density, targeting ability, and capacity of coincorporation of NIR fluorescent dye and chemotherapeutic agent. The dual-agent-loaded micelles display enhanced cytotoxicity with the irradiation of NIR laser through combination effect of hypothermia and chemotherapeutic therapy.

    17. Hetero-difunctional dimers as building blocks for the synthesis of poly(amidoamine)s with hetero-difunctional chain terminals and their derivatives (pages 4947–4957)

      Paolo Ferruti, Nicolò Mauro, Amedea Manfredi and Elisabetta Ranucci

      Article first published online: 29 AUG 2012 | DOI: 10.1002/pola.26325

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      Hetero-difunctional dimers (HDDs) corresponding to the mono-addition products of amines and bisacrylamides were synthesized and used as building-blocks for the preparation of poly(amidoamine)s with heterodifunctional terminals as well as of a series of hardly obtainable macromolecular architectures such as star-like poly(amidoamine)s, graft-poly(amidoamine)s-protein conjugates, and “tadpole-like” poly(amidoamine)-cholesterol conjugates able to self-assemble into nanoparticles in aqueous media.

    18. Homo- and diblock copolymers of poly(furfuryl glycidyl ether) by living anionic polymerization: Toward reversibly core-crosslinked micelles (pages 4958–4965)

      Markus J. Barthel, Tobias Rudolph, Sarah Crotty, Felix H. Schacher and Ulrich S. Schubert

      Article first published online: 29 AUG 2012 | DOI: 10.1002/pola.26327

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      Well-defined polymers containing poly(furfuryl glycidyl ether) (PFGE) were synthesized by living anionic ring-opening polymerization and characterized by SEC, MALDI-TOF MS and 1H NMR spectroscopy. Micelles formed by PEG-b-PFGE in water were used to incorporate a suitable bismaleimide. Heating to 60 °C induced the crosslinking of the micellar core via Diels-Alder chemistry. This process was further shown to be reversible.

    19. In situ polymerization and morphology of polypyrrole obtained in water-soluble polymer templates (pages 4966–4976)

      Simona Percec, Conor Bolas, Laurie Howe, Donald J. Brill and Jing Li

      Article first published online: 29 AUG 2012 | DOI: 10.1002/pola.26328

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      Polymerization of pyrrole with FeCl3 as an oxidant in a series of polymer aqueous templates showed that only in the presence of polyvinyl alcohol (PVA) are nanosized polypyrrole particles obtained. 1H NMR kinetic experiments of this reaction using ammonium persulfate as an oxidant indicated increased reaction rate with higher molecular weight and concentration of PVA. Correlations with particle size of nanospheres obtained with FeCl3 indicated an inversely proportional relationship between the reaction rate and the nanosphere size.

    20. A novel benzimidazole-containing phthalonitrile monomer with unique polymerization behavior (pages 4977–4982)

      Dimeng Wu, Yongchao Zhao, Ke Zeng and Gang Yang

      Article first published online: 29 AUG 2012 | DOI: 10.1002/pola.26331

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      In this work, a novel benzimidazole-containing phthalonitrile monomer (BIPN) was synthesized. The self-promoted polymerization reaction of the BIPN was unexpectedly sluggish. Therefore, high temperature resins with unprecedented polymerization behavior (outstanding melt stability (>300 °C) and low polymerization exothermic effect) were realized. The results open a new entrance for designing high temperature/performance resins, where the molecular weight range of the aromatic heterocyclic spacers can be broadened and more flexible chemical structures can be introduced into the spacers of the resins.

    21. Copper(0)-mediated radical copolymerization of vinyl acetate and acrylonitrile in DMSO at ambient temperature (pages 4983–4989)

      Huali Yu, Yang Wu, Jinlong Gao, Wenxiang Wang, Zhengbiao Zhang and Xiulin Zhu

      Article first published online: 24 AUG 2012 | DOI: 10.1002/pola.26334

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      The homopolymerization of vinyl acetate (VAc) cannot be well controlled by Cu(0)-mediated controlled radical polymerization (CRP) technique at 25 °C. This work explores the Cu(0)-mediated radical copolymerization of VAc and acrylonitrile (AN) at 25 °C. At low VAc feed ratios, the polymerization conveys moderately controlled manners. The reactivity ratios of VAc and AN in the system are found to be 0.003 and 1.605, respectively. The work provides the first example of copolymerization of VAc and AN at room temperature, which will eventually reinforce and enrich the Cu(0)-mediated CRP technique.

  4. Notes

    1. Top of page
    2. Cover Image
    3. Rapid Communication
    4. Articles
    5. Notes
    1. Preparation of a molecularly imprinted polymer containing Europium(III) ions for luminescent sensing (pages 4990–4994)

      Hyungwoo Kim, Youngdo Kim and Ji Young Chang

      Article first published online: 24 AUG 2012 | DOI: 10.1002/pola.26314

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      A molecularly imprinted polymer containing europium(III) ions in binding cavities is prepared. A chromophoric template molecule is captured selectively in the cavities and detected directly by observing the sensitized luminescence of the europium(III) ions. This type of sensor may be suitable for detecting chromophoric toxic chemicals, such as aromatic acid herbicides and insecticides.

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