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  • 1
    Electronic Resource
    Electronic Resource
    Radical polymerization of N-phenyl-α-methylene-β-lactam (1990)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 28 (1990), S. 2597-2607 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: N-phenyl-α-methylene-β-lactam (PML), a cyclic analog of N,N-disubstituted methacrylamides which do not undergo radical homopolymerization, was synthesized and polymerized with α,α′-azobis (isobutyronitrile) (AIBN) in solution. Poly (PML) (PPML) is readily soluble in tetrahydrofuran, chloroform, pyridine, and polar aprotic solvents but insoluble in toluene, ethyl acetate, and methanol. PPML obtained by radical initiation is highly syndiotactic (rr = 92%), exhibits a glass transition at 180°C, and loses no weight upto 330°C in nitrogen. The kinetics of PML homo-polymerization with AIBN was investigated in N-methyl-2-pyrrolidone. The rate of polymerization (Rp) can be expressed by Rp = k[AIBN]0.55[PML]1.2 and the overall activation energy has been calculated to be 87.3 kJ/mol. Monomer reactivity ratios in copolymerization of PML (M2) with styrene (M1) are r1 = 0.67 and r2 = 0.41, from which Q and e values of PML are calculated as 0.60 and 0.33, respectively.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1990.080281002
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  • 2
    Electronic Resource
    Electronic Resource
    Radical polymerization of 4-methylene-4H-1,3-benzodioxin-2-ones: Cyclic α-substituted styrenes (1993)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 31 (1993), S. 1895-1902 
    Details
    ISSN: 0887-624X
    Keywords: 4-methylene-4H-1,3-benzodioxin-2-one ; exo-methylene cyclic monomers ; radical polymerization ; kinetics ; monomer reactivity ratios ; chemical amplification ; decarboxylation ; poly[(o-hydroxyphenyl)acetylene] ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 4-Methylene-4H-1,3-benzodioxin-2-one (MBDOON), an α-substituted cyclic styrene derivative, was synthesized and polymerized readily with 2,2′-azobis(isobutyronitrile) (AIBN) as an initiator in solution. The kinetics of the MBDOON homopolymerization with AIBN was investigated in N-methyl-2-pyrrolidone (NMP). The rate of polymerization, Rp, can be expressed by Rp - k[AIBN]0.52[MBDOON]1.1 and the overall activation energy has been calcualted to be 75.7 kJ/mol. Monomer reactivity ratios in copolymerization of MBDOON (M2) with styrene (M1) are r1 = 0.31 and r2 = 3.20, from which Q and e values of MBDOON can be calculated as 3.0 and -0.7, respectively. Ring-substituted MBDOON monomers such as 6-chloro, 6-methyl, and 7-methoxy derivatives were synthesized and polymerized with AIBN. The 6-substituted MBDOON's readily underwent radical polymerization while the 7-methoxy-MBDOON was slower to polymerize. Poly(MBDOON) is predominantly heterotactic. (rr = 35, mr = 46, and mm = 19%). The polymer releases carbon dioxide at about 200°C and is converted with some depolymerization to poly[(o-hydroxyphenyl)acetylene]. The thermolysis temperature is very much affected by the ring substituent. The onset of carbon dioxide liberation was observed at 140°C in the case of the 7-methoxyl derivative while the 6-substituents had a smaller effect on the decarboxylation temperature. © 1993 John Wiley & Sons, Inc.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1993.080310728
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  • 3
    Electronic Resource
    Electronic Resource
    Radical reactivity of α-trifluoromethylstyrene (1988)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 26 (1988), S. 89-98 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: α-Trifluoromethylstyrene (TFMST) does not undergo radical homopolymerization with azobis(isobutyronitrile) (AIBN) in bulk at 60°:C. Low-temperature initiation was not effective either. Radical copolymerization of TFMST (M2) with styrene (ST, M1) has yielded monomer reactivity ratios as follows: r1 =: 0.60 and r2 =: 0.00. It has been found that the cyclohexyl radical generated by reaction of cyclohexylmercuric chloride with sodium borohydride adds to the β-carbon of TFMST 7.5 times faster than that of ST. Combination of the copolymerization analysis and the “mercury method” has allowed us to estimate Alfrey-Price Q and e parameters for TFMST to be 0.43 and 0.90, respectively. Thus, due to the strongly electron-withdrawing effect of the trifluoromethyl group, this styrene is highly electron deficient. In spite of the favorable electronic effect, however, the ceiling temperature appears very low, presumably due to the steric hindrance.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1988.080260109
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  • 4
    Electronic Resource
    Electronic Resource
    Elementary reaction and anionic polymerization of isopropenly t-butyl ketone (1991)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 29 (1991), S. 1001-1013 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Isopropenyl t-butyl ketone (IPTBK) does not undergo radical homopolymerization and its anionic polymerization is a slow equilibrium process with a low ceiling temperature, which is due to its limited conjugation imposed by steric hindrance. Equimolar reactions of IPTBK with several anionic initiators were carried out, products isolated and identified by 1H-and 13C-NMR, and product distributions determined by GC. While n-butyllithium and phenyllithium preferentially produce allyl alcohols, Grignard reagents predominantly undergo β-addition to produce mono-adducts, and a significant amount of dimers. t-Butyllithium and t-butylmagnesium chloride provide the cleanest β-addition with minimal dimer formation and no carbonyl addition. However, Grignard reagent do not yield a polymer. The 1:1 reaction mixture of IPTBK with t-butyllithium is very stable at 0°C, providing a methyl-terminated mono-adduct quantitatively when quenched with methyl iodide after 29 h. Addition of a second IPTBK to the mono-adduct anion appears to be affected by the low ceiling temperature. Although t-butyllithium can efficiently reduce as well as add to di-t-butyl ketone, such reactions are minor in the presence of IPTBK. Anionic polymerization of IPTBK with t-butyllithium was carried out under several conditions. The 1:1 model reactions and the lack of acidic hydrogens in its structure suggest that anionic polymerization of IPTBK with t-butyllithium may be “living.” The molecular weight distribution of the polymers ranged from 1.1 to 1.6 with the number-average molecular weight varying from 2,800 to 233,500. Group transfer polymerization of IPTBK produced only a six-membered lactone.
    Additional Material: 11 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1991.080290707
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  • 5
    Electronic Resource
    Electronic Resource
    Polymerization of α-methyleneindane: A cyclic analog of α-methylstyrene (1991)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 29 (1991), S. 1779-1787 
    Details
    ISSN: 0887-624X
    Keywords: α-methyleneindane ; tacticities ; monomer reactivity ratios ; exo-methylene cyclic monomers ; depropagation ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: α-Methyleniedane (MI), a cyclic analog of α-methylstyrene which does not undergo radical homopolymerization under standard conditions, was synthesized and subjected to radical, cationic, and anionic polymerizations. MI undergoes radical polymerization with α,α′-azobis(isobutyronitrile) in contrast to α-methylstyrene, owing to its reduced steric hindrance, though the polymerization is slow even in bulk. Cationic and anionic polymerization of MI with BF3OEt2 and n-butyllithium, respectively, proceed rapidly. The thermal degradation behavior of the polymer depends on the polymerization conditions. The anionic and radical polymers are heteortactic-rich. Reactivity ratios in bulk radical copolymerization on MI (M2) with methacrylate (MMA, M1) were determined at 60°C (r1 = 0.129 and r2 = 1.07). In order to clarify the copolymerization mechanism, radical copolymerization of MI with MMA was investigated in bulk at temperatures ranging from 50 to 80°C. The Mayo-Lewis equation has been found to be inadequate to describe the result due to depolymerization of MI sequences above 70°C.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1991.080291210
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  • 6
    Electronic Resource
    Electronic Resource
    Chain scission efficiency and reactive-ion etch resistance of alternating copolymers of styrene and olefins trisubstituted or tetrasubstituted with electron-withdrawing groups (1986)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 24 (1986), S. 955-964 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Alternating copolymers of styrene (St) with electron-deficient olefins trisubstituted or tetrasubstituted with cyano and carboalkoxy groups have been subjected to 60Co γ-radiolysis together with a series of copolymers of methyl methacrylate (MMA) and St. The chain scission susceptibility Gs - Gx determined by membrane osmometry drastically decreases as St is incorporated in poly(methyl methacrylate) (PMMA). Whereas the alternating St-MMA copolymer is slightly crosslinked upon irradiation, an alternating copolymer of St with diethyl 2-cyano-1,1-ethylenedicarboxylate maintains a fairly high degradation sensitivity (Gs - Gx = 1.2). The reactive-ion etch rates were determined for the series of polymers in CF4/O2 (92/8). The etch resistance is significantly increased by introduction of St units in PMMA, and the highly substituted alternating copolymer etches as slowly as the MMA(50) - St(50) copolymers. Thus the alternating copolymer of NCCH=C(CO2Et)2 with St behaves like PMMA when exposed to high-energy radiation but is comparable to PSt in plasma environments.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1986.080240513
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  • 7
    Electronic Resource
    Electronic Resource
    Thermal deesterification and decarboxylation of alternating copolymers of styrene with β-substituted t-butyl α-cyanoacrylates (1989)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 27 (1989), S. 2871-2881 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Alternating copolymers of styrene with β-carboalkoxy-substituted t-butyl α-cyanoacrylates undergo facile deesterification at 150-190°C, about 60°C below the deprotection temperature of poly(t-butyl methacrylate), and decarboxylation at 170-200°C. When the β-substituent is a methyl ester, the two events are clearly separated, with the deesterification occurring at a maximum rate at 165°C and decarboxylation at 193°C. Anhydride formation is negligible in this case. The copolymer with t-butyl cyanofumarate exhibits simultaneous deesterification and decarboxylation events at 180°C with concomitant minor dehydration.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1989.080270904
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  • 8
    Electronic Resource
    Electronic Resource
    Radical polymerization of 3-methylene-5,5′-dimethyl-2-pyrrolidinone: A cyclic analog of N-substituted methacrylamide (1993)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 31 (1993), S. 949-955 
    Details
    ISSN: 0887-624X
    Keywords: radical polymerization ; 3-methylene-5,5′-dimethyl-2-pyrrolidinone ; exomethylene cyclic monomers ; kinetics ; monomer reactivity ratios ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 3-Methylene-5,5′-dimethyl-2-pyrrolidinone (α-MDMP), a cyclic analog of N-substituted methacrylamide, was synthesized and polymerized with α,α′-azobis (isobutyronitrile) (AIBN) in solution. Poly(α-MDMP) is only soluble in dimethyl sulfoxide (DMSO) at room temperature. Thermogravimetry of poly(α-MDMP) showed 10% weight loss at 355°C in air and 400°C under nitrogen, respectively. The kinetics of α-MDMP homopolymerization with AIBN was investigated in DMSO. The rate of polymerization (Rp) can be expressed by Rp = k[AIBN]0.49[α-MDMP]1.0 and the overall activation energy has been calculated to be 73.2 kJ/mol. Monomer reactivity ratios in copolymerization of α-MDMP (M2) with methyl methacrylate (M1) are r1 = 0.71 and r2 = 0.71, from which Q and e values of α-MDMP are calculated as 0.75 and -0.43, respectively. © 1993 John Wiley & Sons, Inc.
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1993.080310413
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  • 9
    Electronic Resource
    Electronic Resource
    Solid-state thermolysis of poly(p-t-butoxycarbonyloxystyrene) catalyzed by polymeric phenol: Effect of phase separation (1986)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 24 (1986), S. 2971-2980 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Thermolysis of poly(p-t-butoxycarbonyloxystyrene) (PBOCST) catalyzed by polymeric phenol in the solid state is very much dependent on the extent of phase separation. Poly(p-hydroxystyrene) (PHOST, a thermolysis product of PBOCST) is not miscible with PBOCST. Therefore, this phenolic resin can not effectively catalyze the solid-state thermolysis reaction when simply blended with PBOCST. However, if the phenolic functionality is forced to be in the vicinity of the t-butoxycarbonyl (tBOC) group, the thermolysis takes place facilely at 130°C. The effect of casting solvent on thermolysis in PBOCST/Varcum films is also discussed.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1986.080241124
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  • 10
    Electronic Resource
    Electronic Resource
    Reactivities of methacrylate derivatives in radical polymerization as evaluated by mercury method (1988)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 26 (1988), S. 2395-2404 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactivities of methyl methacrylate derivatives bearing substituents on the ester methyl group have been investigated by competitively adding a cyclohexyl radical generated by a reaction of cyclohexylmercuric chloride with sodium borohydride (mercury method) to these substituted methacrylates and methyl methacrylate or styrene. The relative rate constants of the cyclohexyl radical addition have been found to be nicely correlated with parameters such as Traft α* constants of alkyl esters, Q-e values, lowest unoccupied molecular orbital energies, β-carbon chemical shifts, and relative reactivities toward a polystyryl radical, indicating that the mercury method is a simple and useful technique for evaluation of the relationship between structure and reactivity of vinyl monomers in their radical polymerization, even when the structural modification is small.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1988.080260912
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