The Copolymerization of Vinylhydroquinone and Acrylonitrile by Tri-n-butylborane

ZUSAMMENFASSUNG:Die Copolymerisation von 4-Propenylbrenzcatechin-Derivaten, wie Eugenol (I), Isosafrol(2), und Safrol(3), mit Vinylmonomeren, wie Acrylnitril (AN), Maleinsaureanhydrid (MA), und Methylmethacrylat (MMA), durch Tributylboran (TBB) wurde in Cyclohexanon bei 30°C unter Stickstoff untersucht. Die Propenylverbindungen copolymerisierten mit AN und MA, wahrend MMA mit ihnen nur Homopolymeres ergab.Fur die Systeme AN/Propenylbrenzcatechin-DerivatPBB wurden die folgenden Copolymerisationsparameter erhalten (MI =AN): AN/I,TBB-System: r = 2,2 und r2 =0, AN/2/TBB-System: r l =0,28 und r2=O, AN/3/TBB-System: r l = 1,8 und r2=0. Dieses Resultat entspricht der Tatsache, daD die Propenylverbindungen 1-3 unter diesen Reaktionsbedingungen nicht homopolymerisierten.Das MA/2/TBB-System ergab 1 : 1-Copolymere; die Copolymerisation verlief wahrscheinlich uber einen CT-Komplex-Mechanismus. SUMMARY:The copolymerization of 4-propenylpyrocatechol derivatives, eugenol (I), isosafrole (2), and safrole (3), with vinyl monomers such as acrylonitrile (AN), maleic anhydride (MA), and methyl methacrylate (MMA), by tributylborane (TBB) was investigated in cyclohexanone at 30°C in a nitrogen atmosphere. These propenyl compounds copolymerized with AN and MA. However, only homopolymerization occurred when they were reacted with MMA under the same conditions.The following monomer reactivity ratios were determined for the systems AN/propenylpyrocatechin derivative/TBB (M =AN): AN/lpBB-system: r = 2,2 and r 2 = 0 , AN/Z/TBB-system: r l =0,28 and r2=0, AN/3/TBB-system: r l = 1,s and r2=0. This result *) Prof. Dr. Volker Jaacks, der 1971 im Himalaya-Gebirge todlich verungliickte, zum 40. Geburtstag gewidmet.Makromol. Chem. 176, No. 2, Februar 1975 255

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Vinylhydroquinone. III. Copolymerization of vinylhydroquinone and vinyl monomers by tri‐n‐butylborane

Iwabuchi

Kojima

Nakahira

et al. 1974

J. Polym. Sci. Polym. Chem. Ed.

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The copolymerization of vinylhydroquinone (VHQ) and vinyl monomers, e.g., methyl methacrylate (MMA), 4‐vinyl‐pyridine (4VP), acrylamide (AA), and vinyl acetate (VAc), by tri‐n‐butylborane (TBB) was investigated in cyclohexanone at 30°C under nitrogen. VHQ is assumed to copolymerize with MMA, 4VP, and AA by vinyl polymerization. The following monomer reactivity ratios were obtained (VHQ = M2): for MMA/VHQ/TBB, r1 = 0.62, r2 = 0.17; for 4VP/VHQ/TBB, r1 = 0.57, r2 = 0.05; for AA/VHQ/TBB, r1 = 0.35, r2 = 0.08. The Q and e values of VHQ were estimated on the basis of these reactivity ratios as Q = 1.4 and e = −;1.1, which are similar to those of styrene. This suggests that VHQ behaves like styrene rather than as an inhibitor in the TBB‐initiated copolymerization. No homopolymerization was observed either under nitrogen or in the presence of oxygen. The reaction mechanism is discussed.

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The Copolymerization of Vinylhydroquinone and Acrylonitrile by Tri-n-butylborane

Cited by 12 publications

References 25 publications

Free Radical Copolymerization Reactivity Ratios

Free Radical Copolymerization Reactivity Ratios

Polymere brenzcatechin‐derivate, 1. Über die Copolymerisation von 4‐Propenylbrenzcatechin‐Derivaten mit Vinylmonomeren durch Tributylboran

Vinylhydroquinone. III. Copolymerization of vinylhydroquinone and vinyl monomers by tri‐n‐butylborane

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