Journal of Polymer Science Part A: Polymer Chemistry

Cover image for Vol. 46 Issue 24

15 December 2008

Volume 46, Issue 24

Pages 7925–8212

  1. Articles

    1. Top of page
    2. Articles
    3. Notes
    1. Synthesis of self-healing supramolecular rubbers from fatty acid derivatives, diethylene triamine, and urea (pages 7925–7936)

      Damien Montarnal, Philippe Cordier, Corinne Soulié-Ziakovic, François Tournilhac and Ludwik Leibler

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23094

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      The synthesis of self-healing supramolecular rubbers is described. Vegetable oil derivatives are used as the starting material. A two-step condensation with amines and urea is used to produce a controlled assembly of H-bonding molecules. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    2. Novel organosoluble aromatic polyimides bearing pendant methoxy-substituted triphenylamine moieties: Synthesis, electrochromic, and gas separation properties (pages 7937–7949)

      Cha-Wen Chang, Hung-Ju Yen, Kuan-Yeh Huang, Jui-Ming Yeh and Guey-Sheng Liou

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23082

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      Four series of polyimides with pendant triphenylamine units were prepared from the diamines with two commercially available tetracarboxylic dianhydrides via a conventional two-step chemical imidization. All the polyimides were amorphous and had useful levels of thermal stability with good solubility. The polymer films exhibited one or two reversible oxidation couple and revealed electrochromic characteristics, with a color change from neutral pale yellowish to green and blue doped form at applied potentials. Gas permeability analyses of some polyimides for CO2, CH4, O2, and N2 were also investigated. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    3. Functionalization of three-dimensionally ordered macroporous cross-linked polystyrene by atom-transfer radical polymerization of hydroxyethyl methacrylate and subsequent derivatization (pages 7950–7959)

      Xu Zhang, Weidong Yan, Huifang Yang, Binyuan Liu and Pange Liu

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23085

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      The SEM image of PHEMA-grafted 3DOM CLPS, which was prepared by graft polymerization of HEMA from the pore wall of 3DOM CLPS via surface-initiated ATRP. The PHEMA-grafted 3DOM CLPS also can be further derivatized with a variety of molecules to introduce different functional groups.

    4. New host homopolymers containing pendant triphenylamine derivatives: Synthesis, optical, electrochemical properties and its blend with Ir(ppy)3 for green phosphorescent organic light-emitting devices (pages 7960–7971)

      Chih-Cheng Lee, Kun-Ming Yeh and Yun Chen

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23086

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      Host homopolymers poly(N-(4-(4-(4-vinylbenzyloxy)styryl)phenyl)-N-phenylbenzenamine) (PVST) and poly(4-vinyltriphenylamine) (PTPA) containing hole-transporting triphenylamine chromophores were synthesized by radical copolymerization. The photoluminescence (PL) and electroluminescent (EL) spectra of the blends [PTPA:Ir(ppy)3] showed dominant green emission attributed to Ir(ppy)3 due to efficient energy transfer. The HOMO levels of PVST and PTPA were −5.14 and −5.36 eV, which are much higher than −5.8 eV of PVK. The PTPA device exhibited the best performance with the maximum luminance and maximum luminance efficiency being 9220 cd/m2 and 6.1 cd/A, respectively.

    5. Acrylate based anticorrosion films using novel bis-phosphonic methacrylates (pages 7972–7984)

      Kamel Chougrani, Bernard Boutevin, Ghislain David, Shane Seabrook and Cédric Loubat

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23097

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      Methyl methacrylate monomers exhibiting bisphosphonic functionality were synthesized and tested for their anticorrosive and adhesion properties. The MAC3P2(OH)4 monomer, cured via UV with acrylates, showed excellent resistance to corrosion according to the salt-spray test, for duration of up to 40 days.

    6. Copolymerization of amino acid and amino ester functionalized norbornenes via living ring-opening metathesis polymerization (pages 7985–7995)

      Stefano C. G. Biagini, Vernon C. Gibson, Matthew R. Giles, Edward L. Marshall and Michael North

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23098

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      A series of copolymers based on different amino acid and amino ester functionalized norbornenes have been prepared by ring-opening metathesis polymerization (ROMP), using either the initiator molybdenum [Mo([DOUBLE BOND]N-2,6-iPr[BOND]C6H3)([DOUBLE BOND]CHCMe2)Ph)(OCMe3)2] or ruthernium [Ru(PCy)2Cl2([DOUBLE BOND]CHPh)].

    7. Linear polyurethanes made from threitol: Acetalized and hydroxylated polymers (pages 7996–8012)

      Romina Marín and Sebastián Muñoz-Guerra

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23099

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      Acetalized-threitol-derived polyurethanes can be deprotected with aqueous trifluoroacetic acid to produce polyurethanes bearing free hydroxyl side groups which are degradable by water at pH 7.4.

    8. Benzophenone-(phenylthio)acetic acid phosphonium salts as initiators of free-radical photopolymerization of vinyl monomers: Mechanistic studies (pages 8013–8022)

      Jarogniew Bartoszewicz, Gordon L. Hug, Marek Pietrzak, Halina Kozubek, Jerzy Paczkowski and Bronislaw Marciniak

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23100

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      Phosphonium salts of (phenylthio)acetic acid are shown to be efficient coinitiators for photoinduced free-radical polymerization of vinyl monomers. The free radical that is primarily responsible for the initiation step of the polymerization was identified. To understand what factors affect the efficiency of these salts to function as coinitiators the mechanism of primary and secondary photochemical reactions was investigated in the isolated coinitiation system with benzophenone as the photosensitizer. The role of the phosphonium cation was determined as a potential facilitator of the initiation process. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    9. Sulfonation of metallocene-based polyolefinic elastomers and its influence on physicomechanical properties: Effect of reaction parameters, styrene grafting, and pendant chain length (pages 8023–8040)

      Anjan Biswas, Abhijit Bandyopadhyay, Nikhil K. Singha and Anil K. Bhowmick

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23101

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      A new class of sulfonated elastomers has been prepared by direct and styrene-mediated sulfonations of metallocene-based poly(ethylene octene) and poly(ethylene butene) elastomers to impart polarity on the completely nonpolar rubbery matrices. The influence of reaction parameters, pendant chain length, and styrene grafting on the sulfonation reaction and the effect of these modifications on various physicomechanical properties were also studied.

    10. Highly ordered nanoporous thin films by blending of PSt-b-PMMA block copolymers and PEO additives as structure directing agents (pages 8041–8048)

      Sung Chan Park, Hyunjung Jung, Ken-ichi Fukukawa, Luis M. Campos, Kyunghee Lee, Kyusoon Shin, Craig J. Hawker, Jeong Sook Ha and Joona Bang

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23102

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      A simple and robust method for producing nanoporous templates with a high degree of lateral ordering by self-assembly of block copolymers is described. A key strategy is to control the orientation of microdomains in PSt-b-PMMA thin films by using hydrophilic PEO additives as structure directing agents, which induce the perpendicular orientation of PMMA cylinders with good lateral ordering after the solvent annealing under controlled humidity conditions.

    11. Cyclic alkoxyamines for nitroxide-mediated radical polymerization (pages 8049–8069)

      Jean Ruehl, Niwat Ningnuek, Thanchanok Thongpaisanwong and Rebecca Braslau

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23103

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      A 5-membered cyclic alkoxyamine and a 17-membered cyclic alkoxyamine were synthesized and used in the polymerization of styrene. Polymerizations using the 5-membered cyclic alkoxyamine resulted in polymers with uncontrolled molecular weights and high polydispersities. Polymerizations using the 17-membered alkoxyamine produced oligomeric polymers in which multiple polymer chains are linked through NO[BOND]C bonds. EPR homolysis experiments revealed that the 5-membered cyclic alkoxyamine does not dissociate to form a nitroxide species, even at temperatures as high as 403 K. In contrast, the 17-membered cyclic alkoxyamine does dissociate to form nitroxide, but the rate of dissociation is slower than that of parent acyclic alkoxyamine 2,2,5-trimethyl-3-(1-phenylethoxy)-4-phenyl-3-azahexane. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    12. New chemosensory materials based on disubstituted polyacetylene with strong green fluorescence (pages 8070–8080)

      Qi Zeng, Jacky W. Y. Lam, Cathy K. W. Jim, Anjun Qin, Jingui Qin, Zhen Li and Ben Zhong Tang

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23104

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      A new imidazole-containing disubstituted polyacetylene (P1) with strong green fluorescence was successfully prepared through polymer reaction, which was nearly impossible to be obtained from the direct polymerization of its corresponding monomer. Similar as other imidazole-containing conjugated polymers, P1 could probe trace metal ions, such as copper ions. Interestingly, through an indirect trick, P1 was also a good cyanide chemosensor, which could report the presence of trace cyanide at the concentration as low as 0.70 ppm. Thus, this piece of work might open up a new avenue for the development of new anion chemosensors. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    13. Synthesis of P(AA-SA)/ZnO composite latex particles via inverse miniemulsion polymerization and its application in pH regulation and UV shielding (pages 8081–8090)

      Ying-Da Luo, Chi-An Dai and Wen-Yen Chiu

      Article first published online: 11 NOV 2008 | DOI: 10.1002/pola.23105

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      P(AA-SA)/ZnO composite latex particles with UV shielding property and pH regulation capacity were produced successfully via inverse miniemulsion polymerization in this work. The ZnO nanoparticles had undergone oleic acid surface treatment for dispersing in solvent and cyclohexane, and they were located on the surface of P(AA-SA) latex particles after polymerization.

    14. The effect of a trithiol and inorganic fillers on the photo-induced thermal frontal polymerization of a triacrylate (pages 8091–8096)

      Charles Nason, John A. Pojman and Charles Hoyle

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23106

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      The front velocity for the frontal polymerization of a triacrylate as a function of added trithiol, with two different fillers.

    15. Synthesis, characterization, and bulk properties of amphiphilic copolymers containing fluorinated methacrylates from sequential copper-mediated radical polymerization (pages 8097–8111)

      Natanya M. L. Hansen, Michael Gerstenberg, David M. Haddleton and Søren Hvilsted

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23107

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      2,2,2-trifluoroethyl methacrylate (3FM), 2,2,3,3,4,4,5,5-octafluoropentyl methacrylate, and 1,1,2,2-tetrahydroperfluorodecyl methacrylate have been copolymerized with methyl methacrylate via ATRP catalyzed by Cu(I)Br/N-(n-propyl)-2-pyridylmethanimine. 3FM was furthermore copolymerized with 2-methoxyethyl acrylate and poly(ethylene glycol) methyl ether methacrylate. Homopolymerization of 3FM at temperatures of 80–110 °C yielded kpapp of 1.6·10−4 s−1 to 2.9·10−4 s−1 and Ea of 24 kJ/mol. The thermal stability of the fluorinated poly(methacrylates) in inert atmosphere is less than that of the nonfluorinated poly((meth)acrylates). In all instances, the presence of fluorinated blocks significantly increases the advancing water contact angle (up to 118°) of thin films deposited on glass in comparison to equivalent nonfluorinated films.

    16. Persistent and emission color tunable poly(phenylene-ethynylene)s covered with polyhedral oligomeric silsesquioxanes (pages 8112–8116)

      Junpei Miyake and Yoshiki Chujo

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23108

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      The development of chemically and thermally persistent blue-, and green-luminescent hybrid π-conjugated polymers consisting of poly(phenylene-ethynylene) conjugated backbone wrapped with the rigid three-dimensional POSS units was successfully achieved by means of the Sonogashira–Hagihara coupling reaction. Because of the steric effect of POSS units, the luminescence stability of the conjugated backbone was significantly enhanced. Moreover, emission color was also easily tunable only by changing the ratio of POSS moieties incorporated. [Color figure can be viewed only in the online issue, which is available at www.interscience.wiley.com.]

    17. Synthesis and characterization of soluble polyimides functionalized with carbazole moieties (pages 8117–8130)

      Anu Stella Mathews, Dongjo Kim, Youngkyoo Kim, Il Kim and Chang-Sik Ha

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23109

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      We report here new soluble semiconducting polyimides (PIs) containing carbazole moieties in the side chain. For dianydrides were used pyromellitic anhydride (PMDA) or 2, 2′-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA). The carbazole diamine derivatives are 4″-carbazole-9-yl-[1,1′;2′,1″] terphenyl-4-4′-diamine (CzTPDA) and 2-(3-carbazol-9-yl-propyl)-biphenyl-4,4′-diamine (CzHBPDA). All PIs showed high mechanical strength (>1.5 GPa) and extremely high glass transition temperature (>260 °C). Interestingly, most of PIs exhibited low dielectric constant below 3, whilstile the PI films were optically transparent in the visible range (>∼400 nm). Here are structures of CzTPDA and CzHBPDA synthesized in this work.

    18. Y-shaped poly(ethylene glycol) and poly(trimethylene carbonate) amphiphilic copolymer: Synthesis and for drug delivery (pages 8131–8140)

      Huai-Hong Zhang, Zi-Qun Huang, Bai-Wang Sun, Jia-Xiu Guo, Jian-Li Wang and Yao-Qiang Chen

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23110

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      New Y-shaped (AB2-type) amphiphilic copolymers of poly(ethylene glycol) (PEG) with poly(trimethylene carbonate) (PTMC), PEG-b-(PTMC)2, were successfully synthesized by the ring-opening polymerization of trimethylene carbonate with bishydroxy-modified monomethoxy-PEG (mPEG). The molecular weight of the resultant Y-shaped copolymers increased with the increase of the molar ratio of TMC to mPEG-(OH)2 initiator in feed while the PEG chain length was kept constant. The Y-shaped copolymer mPEG-(PTMC)2 could self-assemble into micelles in aqueous medium and the critical micelle concentration values of the micelles decrease with increase in hydrophobic PTMC block length of mPEG-(PTMC)2. The Y-shaped amphiphilic copolymers are believed to be potential for hydrophobic drug delivery.

    19. Synthesis of carbazole-based light-emitting polymers incorporating 2,5-bis(phenylethenyl)-4-decyloxyanisole as collateral fluorophore (pages 8141–8148)

      Koji Takagi, Tsuyoshi Nakagawa and Hidenobu Takao

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23111

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      We have prepared a series of carbazole-based light- emitting polymer containing various amounts of 2,5-bis(phenylethenyl)-4-decyloxyanisole (PEDA) segment. Although the emission from PFCz-PEDA0 without PEDA segment had a low fluorescence quantum yield due to photo-induced electron transfer, the introduction of PEDA segment brought about fluorescence resonance energy transfer to obtain an emission solely from the PEDA fluorophore, especially in film state.

    20. Synthesis of UV-cured acrylic–silica hybrid nanocomposites from dendritic acrylic oligomer and acrylic-functionalized silica (pages 8149–8158)

      Hau-Chun Chiang, Chia-Hong Liu and Raymond Chien-Chao Tsiang

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23112

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      An acrylic–silica hybrid polymeric nanocomposite, comprising well-distributed silica nanoparticles in acrylic matrix, has been synthesized at a markedly rapid rate from a dendritic acrylic oligomer and an acrylic-functionalized silica via UV-curing.

    21. Preparation of polybenzoxazole fibers via electrospinning and postspun thermal cyclization of polyhydroxyamide (pages 8159–8169)

      Steve Lien-Chung Hsu, Kuen-Shian Lin and Chi Wang

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23113

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      Scheme for PBO electrospun fibers. BisAPAF-IC PBO precursor synthesis, followed by electrospinning of PHA solutions, and thermal cyclization of PBO precursor fibers.

    22. Fluorenyl cardo copolyimides containing poly(ethylene oxide) segments: Synthesis, characterization, and evaluation of properties (pages 8170–8178)

      Eva M. Maya, Dulce M. Muñoz, Angel E. Lozano, Javier de Abajo and Jose G. de la Campa

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23114

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      This article describes the synthesis, characterization and properties (solubility, film forming ability, thermal stability, mechanical properties and water sorption) of novel fluorenyl cardo copolyimides with different poly(ethylene oxide) (PEO) content (30–65%). The thermal degradation of all polymers occurred in two steps at 380 °C and 500 °C associated with the degradation of the PEO segment and with the generalized aromatic polyimide decomposition, respectively. Most of the polymers showed two Tgs at −25 °C and 250 °C that corresponds to the PEO and aromatic polyimides segments respectively. Copolyimides with PEO contents from 30 to 56% were amorphous, showed unusual low water sorption (<6%) and could be cast on tough films with good mechanical properties to be tested as gas separation membranes.

    23. Toward low-band gap dithienophosphole copolymers for an application in organic solar cells (pages 8179–8190)

      Stefan Durben, Debby Nickel, Robin A. Krüger, Todd C. Sutherland and Thomas Baumgartner

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23115

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      A series of dithienophospholes containing AB and ABC-fluorene-copolymers have been synthesized, and their photophysical properties with focus on a potential application in organic solar cells have been investigated. The ABC-copolymer using the benzothiadiazole comonomer (shown on the right) has been found to exhibit a suitable band gap and furthermore shows intermolecular charge transfer processes in the presence of a fullerene acceptor component, which is an important requirement for application in solar cells. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com]

    24. Functionalizable biodegradable photocrosslinked elastomers based on 2-oxepane-1,5-dione (pages 8191–8199)

      Laurianne Timbart and Brian G. Amsden

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23117

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      Biodegradable elastomers with controlled architecture and functionalizable ketone groups along the network backbone were prepared from a star copolymer prepolymer synthesized from ring opening copolymerization of ε-caprolactone with 2-oxepane-1,5-dione initiated with glycerol followed by termini functionalization with acrylate groups. Following photocrosslinking with UV irradiation, the network was effectively reacted with hydrazines yielding either hydroxyl or amine groups along the polymer backbone. These groups can be utilized to tether functional biological moieties, such as peptide ligands, to help support cell attachment, migration, and differentiation in the creation of elastic scaffolds for tissue engineering.

  2. Notes

    1. Top of page
    2. Articles
    3. Notes
    1. You have free access to this content
      A high purity approach to poly(3-hexylthiophene) diblock copolymers (pages 8200–8205)

      Youngmin Lee, Ken-Ichi Fukukawa, Joona Bang, Craig J. Hawker and Jin Kon Kim

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23091

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      Well-defined poly(3-hexylthiophene) P3HT macroinitiators for atom transfer radical polymerization have been prepared by introducing a phenyl group at the ω-bromo-chain end. Capping of the ω-chain end with a phenyl group allows the preparation of high purity P3HT block copolymers.

    2. You have free access to this content
      Synthesis and characterization of the PEG-based nonionic surfactants endowed with carboxylic acid moiety at the hydrophobic terminal (pages 8206–8212)

      Hiroshi Morikawa, Shintaro Koike, Megumi Saiki and Yasuo Saegusa

      Article first published online: 12 NOV 2008 | DOI: 10.1002/pola.23095

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      As a new class of stimulus-responsive surfactants, a series of α-methyl-ω-alkyl PEGs endowed with a carboxylic acid moiety at the hydrophobic terminal was successfully synthesized with 56–97% yields. They were characterized by IR, NMR spectroscopic and MALDI-TOF MS analyses. It is suggested by DLS measurement that the collapse of the micelle-like aggregation occurred under basic condition. This synthetic procedure would be applicable to surfactants with sufficient hydrophilic and lipophilic balances, allowing precise control of pH-responsive micellar systems.

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