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  • 1
    Electronic Resource
    Electronic Resource
    Anionic synthesis of aromatic amide and carboxyl functionalized polymers. Chain-end functionalization of poly(styryl)lithium with N,N-diisopropyl-4-(1-phenylethenyl)benzamide (1998)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 36 (1998), S. 1233-1241 
    Details
    ISSN: 0887-624X
    Keywords: living anionic polymerization ; poly(styryl)lithium ; functionalization ; aromatic carboxylation ; N,N-diisopropylamide ; N,N-diisopropyl-4-(1-phenylethenyl)-benzamide ; substituted 1,1-diphenylethylenes ; functionalized polystyrene ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The novel syntheses of N,N-diisopropyl-4-benzoylbenzamide, N,N-diisopropyl-4-(1-hydroxy-1-phenylethyl)benzamide, and N,N-diisopropyl-4-(1-phenylethenyl)benzamide (1) are described. ω-Amidopolystyrene (2) was synthesized in quantitative yields by the reaction of poly(styryl)lithium with stoichiometric amounts of N,N-diisopropyl-4-(1-phenylethenyl)benzamide (1) in toluene/tetrahydrofuran (4 : 1 v/v) at -78°C. Deblocking of the amide protecting group by acid hydrolysis quantitatively provides the corresponding aromatic carboxyl chain-end functionalized polystyrene (3). The functionalization agent and functionalized polymers were characterized by HPLC, thin-layer chromatography, size exclusion chromatography, vapor phase osmometry, spectroscopy (1H-NMR, 13C-NMR, and FTIR), potentiometry, and elemental analysis. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 1233-1241, 1998
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    A hydrocarbon-soluble difunctional orgaolithium anionic initiator. Synthesis of 2,2-bis[3-(1-lithio-2,3-dimethylpentyl)-4-methoxyphenyl]propane (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Polymer International 34 (1994), S. 163-171 
    Details
    ISSN: 0959-8103
    Keywords: anionic polymerization ; 2,2-bis[3-(1-propenyl)-4-methoxyphenyl]-propane ; difunctional initiator ; organolithium ; intramolecular ether linkage ; nonpolar solvents ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: The reaction of stoichiometric amounts of sec-butyllithium with 2,2-bis[3-(1-propenyl)-4-methoxyphenyl]propane (4) produces a new difunctional organolithium initiator, 2,2-bis[3-(1-lithio-2,3-dimethylpentyl)-4-methoxyphenyl] propane, which is soluble in hydrocarbon solvent in the absence of any polar additive. Following isolation and purification by gas liquid chromatography, the structures of (4) and the methanolysis product of the difunctional initiator were characterized by 1H NMR, FTIR and mass spectroscopy and elemental analysis. The dilithium initiator is effective for the polymerization of 1,3-butadiene and allows the preparation of polybutadienes with predictable molecular weights, narrow, monomodal molecular weight distribution and low 1,2-diene microstructure.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pi.1994.210340207
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  • 3
    Electronic Resource
    Electronic Resource
    Hydrocarbon-soluble difunctional organolithium anionic initiators. A gas-liquid chromatographic study of the reaction of sec-butyllithium with m-divinylbenzene (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Polymer International 35 (1994), S. 263-272 
    Details
    ISSN: 0959-8103
    Keywords: anionic polymerization ; 1,3-bis(1-lithio-3-methylpentyl)benzene ; gas-liquid chromatography ; high purity sec-butyllithium ; difunctional initiator ; nonpolar solvents ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: Quantitative gas-liquid chromatography provides an efficient, novel technique for the kinetic study of the reaction between sec-butyllithium and m-divinylbenzene. The reaction of stoichiometric amounts of ultra-high purity sec-butyllithium with pure m-divinylbenzene at -23°C produces an anionic initiator, 1,3-bis(1-lithio-3-methylpentyl)benzene, 2, without traces of monofunctional and polyfunctional impurities. The relative rates of formation of 2 with and without the presence of Lewis base, triethylamine, or Lewis acid, diethylzinc, were studied by gas-liquid chromatography. The presence of diethylzinc reduces the activity of sec-butyllithium to such an extent that the reaction did not proceed beyond the monofunctional component stage, that is, the formation of m-1-lithio-3-methylpentylvinylbenzene, 1. The reaction of sec-butyllithium with m-divinylbenzene at -79°C with a 10mol% ratio of triethylamine to sec-butyllithium yielded a homogeneous product with composition of 94% difunctionality and 6% monofunctionality, with the total disappearance of m-divinylbenzene as observed by GLC. However, precipitation due to agglomeration was observed at 25°C at 100% conversion.The high purity 1,3-bis(1-lithio-3-methylpentyl)benzene initiator, 2, is effective for the polymerization of 1,3-butadiene and allows the synthesis of polybutadienes with predictable molecular weights and narrow molecular weight distributions. Depending on the polymerization solvent, polybutadienes with microstructures ranging from 9 to 13% 1,2-vinyl content were observed by 1H NMR analysis and FTIR spectroscopy. However, the presence of diethylzinc retards the rate of polymerization of 1,3-butadiene, without any change in polymer microstructure. Triethylamine enhances the rate of 1,2-enchainment without significant reduction in the 1,4-enchainment of polybutadiene.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pi.1994.210350308
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    Paper (German National Licenses)
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  • 4
    Electronic Resource
    Electronic Resource
    Anionic synthesis of aromatic carboxyl functionalized polymers. Chain-end functionalization of poly(styryl)lithium with 4,5-dihydro-4,4-dimethyl-2-[4-(1-phenylethenyl)phenyl] oxazole (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Polymer International 40 (1996), S. 79-86 
    Details
    ISSN: 0959-8103
    Keywords: living anionic polymerization ; poly(styryl)lithium ; functionalization ; aromatic carboxylation ; 1,3-oxazoline group ; macromonomers ; 4,5-dihydro-4,4-dimethyl-2- [4-(1-phenylethenyl)phenyl]oxazole ; substituted 1,1-diphenylethylenes ; functionalized polystyrene ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: The novel syntheses of 4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)benzophenone, 1-[4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)phenyl]-1-phenylethanol and 4,5-dihydro-4,4-dimethyl-2-[4-(1-phenylethenyl)phenyl]oxazole (1) are described. ω-Oxazolyl polystyrene (2) was synthesized in quantitative yields by the reaction of poly(styryl)lithium with stoichiometric amounts of 4,5-dihydro-4,4-dimethyl-2-[4-(1-phenylethenyl)phenyl]oxazole (1) in toluene/tetrahydrofuran (4 : 1 v/v) at -78°C. Deblocking of the oxazoline protecting group by acid hydrolysis followed by saponification quantitatively provides the corresponding aromatic carboxyl chain-end functionalized polystyrene (3). The functionalization agent and functionalized polymers were characterized by HPLC, thin layer chromatography, size exclusion chromatography, vapor phase osmometry, spectroscopy (1H NMR, 13C NMR and FTIR), potentiometry and elemental analysis.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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