Journal of Polymer Science Part A: Polymer Chemistry

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

15 May 2008

Volume 46, Issue 10

Pages 3155–3458

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      Bimolecular radical termination: New perspectives and insights (pages 3155–3173)

      Geoffrey Johnston-Hall and Michael J. Monteiro

      Article first published online: 10 APR 2008 | DOI: 10.1002/pola.22684

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      The RAFT-CLD-T method has allowed us to answer a number of fundamental questions regarding the mechanism of diffusion-controlled bimolecular termination in free-radical polymerization. It was found that the matrix architecture had little or no influence on termination in the dilute regime. Chain overlap (c*) is the main cause for the onset of the gel effect, and the observed autoacceleration in rate observed in free-radical polymerizations. In the concentrated regime, well above c*, we found that the polymer matrix is much more mobile than what is expected if reptation were to dominate. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.].

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    1. SET-LRP of acrylates in the presence of radical inhibitors (pages 3174–3181)

      Gerard Lligadas and Virgil Percec

      Article first published online: 10 APR 2008 | DOI: 10.1002/pola.22635

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      The Cu(0)/Me6-TREN-catalyzed single-electron transfer mediated living radical polymerization (SET-LRP) of methyl acrylate in the presence of the classic 4-methoxyphenol free radical inhibitor was investigated. The reported study demonstrates that SET-LRP is a robust synthetic method that does not require the purification of the monomers in order to remove the radical inhibitor. It is anticipated that these results will contribute to the expansion of technological and fundamental applications of SET-LRP.

    2. New poly(ester amide)s from alkyl 2-(carboethoxyhydroxymethyl)acrylates (pages 3182–3192)

      Jean-François Morizur and Lon J. Mathias

      Article first published online: 10 APR 2008 | DOI: 10.1002/pola.22637

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      The synthesis and characterization of new aliphatic poly(ester amide)s from alkyl 2-(carboethoxyhydroxymethyl)acrylates is described. Real-time NMR spectroscopy permitted monitoring the extent of the reaction sequence and determining the conversion profile of reactants and Michael adduct intermediate. Poly(ester amide)s derived from diamine and hexane bis-2-(carboethoxyhydroxymethyl)acrylate were synthesized at room temperature by means of a very efficient Michael addition/cyclization polymerization. These polymers display excellent adhesion to metal, glass, and paper substrates and interesting hydrolytic susceptibility.

    3. Polyplatinayne/polyoxometalate composite Langmuir-Blodgett films: Preparation, structural characterization, and potential optoelectronic applications (pages 3193–3206)

      Li Liu, Ling-Xiang Qiao, Shi-Zhong Liu, Dong-Mei Cui, Chun-Mei Zhang, Zheng-Ji Zhou, Zu-Liang Du and Wai-Yeung Wong

      Article first published online: 10 APR 2008 | DOI: 10.1002/pola.22654

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      New luminescent organometallic/inorganic nanohybrid Langmuir-Blodgett films based on metallopolyyne polymers of platinum were prepared and characterized by π–A isotherms, low angle X-ray diffraction, atomic force microscopy, and scanning tunneling microscopy. These hybrid LB composites which are shown to display intriguing photoelectric properties have great potential to be used for various optoelectronic applications.

    4. Microwave-assisted ring-opening polymerization of p-dioxanone (pages 3207–3213)

      Yu-Yan Chen, Gang Wu, Zhi-Cheng Qiu, Xiu-Li Wang, Yuan Zhang, Fang Lu and Yu-Zhong Wang

      Article first published online: 10 APR 2008 | DOI: 10.1002/pola.22656

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      The ring-opening polymerization (ROP) of p-dioxanone (PDO) can be carried out under microwave irradiation with triethylaluminum (AlEt3) or tin powder as catalyst. When AlEt3 was used as catalyst, the viscosity-average molecular weight (Mv) of PPDO reached 317,000 g mol−1 and the yield of PPDO achieved 96.0% only at 80 °C in 30 min; when tin powder was used as catalyst, PPDO with Mv of 106,000 g mol−1 was obtained at 100 °C in 210 min. Microwave heating significantly accelerated the ROP of PDO catalyzed by AlEt3 or tin powder, compared with the conventional heating method.

    5. Use of fluorinated maleimide and telechelic bismaleimide for original hydrophobic and oleophobic polymerized networks (pages 3214–3228)

      Aurélien Soules, Cuauhtémoc Pozos Vázquez, Bruno Améduri, Christine Joly-Duhamel, Mohamed Essahli and Bernard Boutevin

      Article first published online: 10 APR 2008 | DOI: 10.1002/pola.22658

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      The synthesis of fluorinated monomaleimide and telechelic bismaleimide and their use as additives for photopolymerizable formulations of telechelic poly(propylene glycol) bismaleimide led to crosslinked materials.

    6. Synthesis and characterization of carboxylic acid-terminated polyisobutylenes (pages 3229–3240)

      Lisa K. Kemp, Andrew B. Donnalley and Robson F. Storey

      Article first published online: 11 APR 2008 | DOI: 10.1002/pola.22662

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      Quasiliving cationic polyisobutylene (PIB) (TiCl4 coinitiated) was quenched with a nucleophile to create exo-olefin-terminated PIB. The olefin was quantitatively ozonized at −78 °C using hexane/methylene chloride/methanol, 62/31/7 (v/v/v) cosolvents. The primary ozonide was reduced using trimethyl phosphite to yield PIB methyl ketone. Tetrahalomethane oxidation was then used to produce carboxylic acid-terminated PIB. NMR spectroscopy and acid-based titration revealed near-quantitative functionalization. Tetrahalomethane oxidation was conducted using CCl4 as both reagent and solvent, or hexane as the solvent with tetra-n-butylammonium chloride as a phase-transfer catalyst and CCl4 in reagent amounts. The latter system was preferred and showed complete conversion within ∼ 4 h.

    7. Renewable resource-based poly (m-phenylenevinylene)s and their statistical copolymers: Synthesis, characterization, and probing of molecular aggregation and Forster energy transfer processes (pages 3241–3256)

      Anish Cyriac, S. R. Amrutha and M. Jayakannan

      Article first published online: 11 APR 2008 | DOI: 10.1002/pola.22663

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      Novel m-phenylenevinylene polymers based on the renewable resource 3-pentadecylphenol were designed for tracing the energy transfer process and molecular aggregation phenomena in the π-conjugated system. The photophysical studies by absorption and emission spectroscopes indicated the efficient Forster energy transfer from the m-conjugated segments to the p-counterpart. The energy transfer process enhances the quantum yield of the copolymers in solution and molecular aggregation became predominant process and quenches the emission intensity in the solid state. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    8. Interfacial adsorption characteristics of ionic polymeric amphiphiles with comb-like structures: Effect of dodecyl and poly(ethylene oxide) side chains (pages 3257–3271)

      K. Chandrasekar and Geetha Baskar

      Article first published online: 11 APR 2008 | DOI: 10.1002/pola.22664

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      The ionic clusters from AMPS provide expanded coil structures at high pH and promote adsorption at the air/solution and hexane/water interface. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    9. Well-controlled 3D skeletal epoxy-based monoliths obtained by polymerization induced phase separation (pages 3272–3281)

      Norio Tsujioka, Norio Ishizuka, Nobuo Tanaka, Takuya Kubo and Ken Hosoya

      Article first published online: 11 APR 2008 | DOI: 10.1002/pola.22665

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      The epoxy-based monoliths possessing highly ordered structures was prepared by polymerization induced phase separation. A mixture of epoxy resins and amine curing agents in polyethylene glycol is kept at constant temperature to afford an epoxy-based monolith. Different morphology of epoxy-based monoliths could be obtained by changing formulation of monomers and porogenic solvents (as shown in SEM).

    10. Synthesis of star poly(1,3-cyclohexadiene): Grafting reaction of poly(1,3-cyclohexadienyl)lithium onto C60 (pages 3282–3293)

      Itaru Natori and Shizue Natori

      Article first published online: 11 APR 2008 | DOI: 10.1002/pola.22668

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      The grafting reaction of poly(1,3-cyclohexadienyl)lithium (PCHDLi) onto fullerene-C60 (C60) was strongly affected by the nucleophilicity of poly(1,3-cyclohexadiene) (PCHD) carbanions and microstructure of the polymer chain, and that progressed via step-by-step reactions. The star PCHD having maximum four arms was obtained from PCHDLi composed of all 1,4-cyclohexadiene (1,4-CHD) units. The rate of grafting reaction was accelerated by the addition of amine. The grafting density of arm PCHD on C60 was decreased with the increasing of the molar ratio of 1,2-cyclohexadiene (1,2-CHD) units. The electron-transfer reaction from PCHD carbanions to C60 did not occur in a nonpolar solvent and a polar solvent.

    11. Controlled polymerization of 2-(diethylamino)ethyl methacrylate and its block copolymer with N-isopropylacrylamide by RAFT polymerization (pages 3294–3305)

      Li Liu, Chenglin Wu, Jiechun Zhang, Mingming Zhang, Yuwei Liu, Xiaojuan Wang and Guoqi Fu

      Article first published online: 11 APR 2008 | DOI: 10.1002/pola.22669

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      Poly(2-(diethylamino)ethyl methacrylate) (PDEAEMA) homopolymers with low polydispersities were synthesized by reversible addition fragmentation chain transfer (RAFT) radical polymerization. It was found that the RAFT polymerization of DEAEMA was under good control in the presence of 4-cyanopentanic acid dithiobenzoate, with 4,4′-azobis(4-cyanopentanoic acid) as the initiator in 1,4-dioxane at 70 °C. Using PDEAEMA macroRAFT agent, pH/thermo double-responsive block copolymer of PDEAEMA and poly (N-isopropylacrylamide) (PDEAEMA-b-PNIPAM) with narrow polydispersity (1.24) was synthesized. The lower critical solution temperature of PDEAEMA-b-PNIPAM block copolymer depended on the environmental pH. This block copolymer has potential applications in gene delivery and drug-delivery systems.

    12. Graft copolymerization of 2-methacryloyloxyethyl phosphorylcholine to cellulose in homogeneous media using atom transfer radical polymerization for providing new hemocompatible coating materials (pages 3306–3313)

      Lifeng Yan and Kazuhiko Ishihara

      Article first published online: 11 APR 2008 | DOI: 10.1002/pola.22670

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      Poly(2-methacryloyloxyethyl phosphorylcholine) (MPC) was grafted onto cellulose in homogeneous media by the ATRP polymerization. The proteins adsorption studies showed that cellulose membranes modified by the as-prepared cell-PMPC owns good protein adsorption resistance, indicates the copolymer is a potential hemocompatible coating material. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    13. Synthesis, characterization, and thermal properties of ring-opening metathesis polynorbornenes and their hydrogenated derivatives bearing various ester and cyano groups (pages 3314–3325)

      Yasushi Nishihara, Seisuke Izawa, Yoshiaki Inoue, Yuushou Nakayama, Takeshi Shiono and Kentaro Takagi

      Article first published online: 11 APR 2008 | DOI: 10.1002/pola.22671

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      The authors investigated living ring-opening metathesis polymerization (ROMP) of doubly functionalized polar norbornenes by a Ru initiator. The subsequent hydrogenation of the double bond in the ROMP polymers was carried out using a Ru-H complex. The comparison of thermal properties of a series of ROMP polymers with those of the hydrogenated derivatives revealed the decrease of glass transition temperatures (Tg), but little change of the 5% decomposition temperature (Td5). By adding PCy3, triethylamine, and methanol to the reaction mixture after living ROMP, the tandem ROMP-hydrogenation of the ROMP polymer generated in situ was accomplished.

    14. Functionalization of carbon nanofibers (CNFs) through atom transfer radical polymerization for the preparation of poly(tert-butyl acrylate)/CNF materials: Spectroscopic, thermal, morphological, and physical characterizations (pages 3326–3335)

      Marcos Ghislandi, Luis Antonio Sanchez de A. Prado, Alejandra de la Vega Oyerviedes, Hans Wittich, Karl Schulte and Ana Barros-Timmons

      Article first published online: 14 APR 2008 | DOI: 10.1002/pola.22672

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      In this work, the preparation as well as the morphological and structural aspects of poly(tert-butyl acrylate)/carbon nanofiber materials obtained through atom transfer radical polymerization (ATRP) process are reported. X-ray diffraction patterns and infrared spectroscopy demonstrated the integrity graphite-like structure of the modified fibers (although some structural defects could be observed by Raman spectroscopy) and the effectiveness of the ATRP process, respectively. Scanning electron microscopy and thermogravimetric analysis indicated a high content of poly (tert-butyl acrylate), which lead to a relative poor thermal stability of the aforementioned CNF-poly(tert-butyl acrylate) when compared with neat carbon nanofibers. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    15. Synthesis and chiroptical properties of poly (p-phenylenevinylene-alt-m-phenylenevinylene) bearing (−)-trans-myrtanoxyl groups on the p-phenylene rings (pages 3336–3343)

      Xiangfeng Li, Chusheng Li, Jiaguo Yan, Jiang Lu and Hui Liang

      Article first published online: 14 APR 2008 | DOI: 10.1002/pola.22673

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      Chiral poly(p-phenylenevinylene-alt-m-phenylenevinylene) bearing (−)-trans-myrtanoxyl groups on the p-phenylene rings (iso-Myr-PMPV-w) was synthesized by Wittig's reaction, and its chiroptical properties were investigated in chlorobenzene solution by circular dichroism. Iso-Myr-PMPV-w showed much stronger Cotton effect than its analogous poly(p-phenylenevinylene) (iso-Myr-PPV-w) with a maximum g value about one order of magnitude higher than that of the later under the same conditions.

    16. Frontal polymerization of diurethane diacrylates (pages 3344–3352)

      Alberto Mariani, Stefano Fiori, Simone Bidali, Valeria Alzari and Giulio Malucelli

      Article first published online: 14 APR 2008 | DOI: 10.1002/pola.22675

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      The image represents a frontal polymerization experiment in which a moving front propagates along a reactor by converting monomer into polymer. In the present work, frontal polymerization has been successfully exploited for the preparation of poly(urethane acrylates). The influence of reaction conditions and a comparison with the classical batch technique are presented and discussed.

    17. Studies on the thermal polymerization of substituted benzoxazine monomers: Electronic effects (pages 3353–3366)

      R. Andreu, J. A. Reina and J. C. Ronda

      Article first published online: 14 APR 2008 | DOI: 10.1002/pola.22677

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      The electronic effects on the polymerization temperature of several 3-phenyl-3,4-dihydro-2-H-1,3-benzoxazine monomers substituted with electron-withdrawing or electron-donating groups in the 6 and 4′ positions are investigated. The thermal polymerization of these benzoxazine monomers is analyzed by differential scanning calorimetry, and the polymerization behavior and the polymer characteristics are related to the electronic character of the substituent and the polymerization mechanism. An important decrease on the maximum of the polymerization temperature is achieved in some cases, thus allowing the design of tailor-made monomers for low-temperature curing.

    18. Influence of nitroxide structure on polystyrene brushes “grafted-from” silicon wafers (pages 3367–3374)

      Roxana-Viorela Ostaci, Caroline Celle, Gérard Seytre, Emmanuel Beyou, Jean-Paul Chapel and Eric Drockenmuller

      Article first published online: 14 APR 2008 | DOI: 10.1002/pola.22678

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      Different triethoxysilyl alkoxyamines were anchored on silicon substrates by Langmuir–Blodgett reactive deposition and then involved in the “grafting-from” polymerization of styrene. Polystyrene brushes with Mn of 8500–66,400 g/mol, grafting densities of 0.3–1.0 chains/nm2, and chain stretching of 40–70% were obtained. Grafting density and degree of stretching of the brushes are strongly influenced by the behavior of the alkoxyamines at the air/water interface. For high surface pressure depositions, SEC of cleaved brushes and chains simultaneously grown in the bulk revealed that the polymerization degree of bulk and surface chains are significantly different. This was not observed for low grafting density alkoxyamines/brushes.

    19. A versatile preparation of azobenzene-dye functionalized colored polymer nanoparticles by surface modification (pages 3375–3386)

      Caroline Cannizzo, Sonia Amigoni-Gerbier, Michel Frigoli and Chantal Larpent

      Article first published online: 14 APR 2008 | DOI: 10.1002/pola.22679

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      The postfunctionalization of reactive polystyrene-based crosslinked nanoparticles (NPs) by various azobenzene chromophores is readily achieved in water and affords a simple and versatile access to a series of colored aqueous colloidal suspensions (“nanolatex”) of dye-tagged NPs. Dye loads ranging from 0.3 to 1.2 mmol/g (400–1800 dyes-per-NP) are obtained by covalent attachment to the surface of functional NPs bearing active groups as chlorobenzyl or polyamines (cyclam or polypropyleneimine dendrimers of first and third generations), produced by one or two steps microemulsion polymerization process. Their remarkable, “solution-like,” reactivity makes functional as NPs valuable building blocks. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

    20. A new photoiniferter/RAFT agent for ambient temperature rapid and well-controlled radical polymerization (pages 3387–3395)

      Mehmet Atilla Tasdelen, Yasemin Yuksel Durmaz, Bunyamin Karagoz, Niyazi Bicak and Yusuf Yagci

      Article first published online: 14 APR 2008 | DOI: 10.1002/pola.22686

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      Phenacyl morpholine-4-dithiocarbamate (PMDC) is synthesized and characterized. Its capability to act as both a photoiniferter and reversible addition fragmentation chain transfer (RAFT) agent for the polymerization of styrene (St) is examined. Polymerization carried out in bulk under UV irradiation at above 300 nm at room temperature shows controlled free radical polymerization characteristics up to 50% conversions and produces well-defined polymers with molecular weights close to those predicted from theory and relatively narrow poyldispersities (Mw/Mn ∼ 1.30). End group determination and block copolymerization with methyl acrylate suggest that morpholino dithiocarbamate groups were attained at the end of the polymer. Photolysis and polymerization studies revealed that polymerization proceeds via both reversible termination and RAFT mechanisms.

    21. Half-titanocene complexes bearing dianionic 6-benzimidazolylpyridyl-2-carboximidate ligands: Synthesis, characterization, and their ethylene polymerization (pages 3396–3410)

      Weiwei Zuo, Shu Zhang, Shaofeng Liu, Xijie Liu and Wen-Hua Sun

      Article first published online: 18 APR 2008 | DOI: 10.1002/pola.22693

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      Half-titanocenes Cp′TiLCl (Cp′ = C5H5, MeC5H4, C5Me5, L = 6-benzimidazolylpyridine-2-carboxylimidic) were found to be highly active and thermally stable toward ethylene polymerization when activated by MAO or MMAO.

    22. Bis(2-(6-methylpyridin-2-yl)-benzimidazolyl)titanium dichloride and titanium bis(6-benzimidazolylpyridine-2-carboxylimidate): Synthesis, characterization, and their catalytic behaviors for ethylene polymerization (pages 3411–3423)

      Shaofeng Liu, Weiwei Zuo, Shu Zhang, Peng Hao, Deligeer Wang and Wen-Hua Sun

      Article first published online: 18 APR 2008 | DOI: 10.1002/pola.22694

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      Bis(2-(6-methylpyridin-2-yl)-benzimidazolyl)titanium dichloride and titanium bis(6-benzimidazolylpyridine-2-carboxylimidate) were synthesized and characterized. All complexes showed high catalytic activity and good thermal stability in ethylene polymerization when activated by MAO.

  3. Rapid Communications

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      Thermal sensitive fluorescent hyperbranched polymer without fluorophores (pages 3424–3428)

      Pingli Wang, Xin Wang, Kun Meng, Song Hong, Xin Liu, He Cheng and Charles C. Han

      Article first published online: 18 APR 2008 | DOI: 10.1002/pola.22692

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      A thermal-light dual response hyperbranched polymer, poly(ethylene imine)-grafted-cyclohexane carboxylic acid (PEI-CCA), was designed and synthesized by introducing hydrophobic cyclohexyl units to the terminals of hyperbranched poly(ethylene imine) (PEI). Proper amounts of hydrophobic cyclohexyl units endue PEI-CCA with a hydrophobic-hydrophilic balance which leads to the thermo-sensitive property. And the peripheral modifier of PEI provides the resultant hyperbranched polymer with strong fluorescence without any traditional fluorophores. Both temperature response and fluorescence response can be controlled by adjusting the ratio of cyclohexyl groups. The intensities of fluorescence changed with temperature, pH and concentration were investigated.

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      Encapsulation of silver nanoparticles within micropores of block copolymers constructed by emulsion-induced method (pages 3429–3432)

      Koji Ishizu, Naomasa Hatoyama, Masataka Makino, Yoko Tokuno and Satoshi Uchida

      Article first published online: 18 APR 2008 | DOI: 10.1002/pola.22661

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      An encapsulation of silver nanoparticles has been developed based on a template technique. Microporous films containing Ag+ ions were constructed by emulsion micelles of PEO-block-PMMA amphiphilic diblock copolymers. Ag+ ions are located around peripheral PEO phases of micropores. Subsequently, Ag nanoparticles (ca. 23 nm in diameter) within the micropore have been prepared by the addition of a chemical reductant, e.g. NaBH4.

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      Self-directed formation of uniform unsaturated macromolecules from acrylate monomers at high temperatures (pages 3433–3437)

      Thomas Junkers, Francesca Bennet, Sandy P. S. Koo and Christopher Barner-Kowollik

      Article first published online: 18 APR 2008 | DOI: 10.1002/pola.22676

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      Structurally highly uniform poly(butyl acrylate) macromonomers are conveniently synthesized via autoinitiated free-radical polymerization at high temperatures in solution of butyl or hexyl acetate without the need to employ any mediating agent. ESI-MS analysis reveals that neither the primary initiating radical nor the empoyed solvent has a large impact on the product distribution. It is further demonstrated that the mechanism of their formation relies on complex addition-fragmentation equilibria not unlike the RAFT mechanism effectively resulting in a self-organization of the reaction. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

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      Hairy particle-supported 4-N,N-dialkylaminopyridine: An efficient and recyclable nucleophilic organocatalyst (pages 3438–3446)

      Bin Zhao, Xiaoming Jiang, Dejin Li, Xueguang Jiang, Thomas G. O'Lenick, Bing Li and Christopher Y. Li

      Article first published online: 18 APR 2008 | DOI: 10.1002/pola.22681

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      A polymer brush-supported 4-N,N-dialkylaminopyridine catalyst was prepared by surface-initiated nitroxide-mediated polymerization from initiator functionalized crosslinked polystyrene particles. The hairy particles efficiently catalyzed the acylation of secondary alcohols and Baylis-Hillman reaction of 4-nitrobenzaldehyde and methyl vinyl ketone, and were recycled at least six times with no or negligible decrease in the reaction yield.

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      Anionic copolymerization of epoxide with bifunctional aromatic lactone derived from 2-methylresorcinol (pages 3447–3451)

      Atsushi Sudo, Kazuya Uenishi and Takeshi Endo

      Article first published online: 18 APR 2008 | DOI: 10.1002/pola.22650

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      A bifunctional six-membered aromatic lactone, which was derived from 2-methylresorcinol by its double cycloadditions with acrylic acid, was applied as a comonomer to imidazole-catalyzed curing reactions of bifunctional epoxides. The lactone moiety and the epoxide underwent copolymerization efficiently to give the corresponding networked polymers with achieving high glass transition temperatures and small curing shrinkage values. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.]

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      Enhanced reactivity of monovinyl acrylates characterized by secondary functionalities toward photopolymerization and Michael addition: Contribution of intramolecular effects (pages 3452–3458)

      Harini Kilambi, Jeffrey W. Stansbury and Christopher N. Bowman

      Article first published online: 18 APR 2008 | DOI: 10.1002/pola.22660

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      Triethylamine catalyzed Michael addition reactions with butyl mercaptopropionate were performed on a variety of acrylates incorporating carbonate, carbamate, cyclic carbonate, hydroxyl and cyano secondary functionalities. It was shown that the incorporation of these secondary functionalities leads to 1–3 order of magnitude enhancement in the Michael addition reaction rate coefficients. Also, a distinct correlation has been observed between the Michael addition reaction kinetics and the average photopolymerization rates of these monomers.

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