Oxazoline Ring-Opening

Fry, Edward M.

doi:10.1021/jo01150a014

Cited by 78 publications

(22 citation statements)

References 9 publications

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“…9 The oxazolinium perchlorates of 2-isopropenyl-2-oxazoline and 2-phenyl-2-oxazoline as cationic initiators were prepared in the same manner as previously described. 11 The perchlorate salt of poly(2-isopropenyl-2-oxazoline) (Poly-IPOZ) was prepared by the same manner as above.…”

Section: Oxazolinium Perchloratementioning

confidence: 99%

Selective Polymerization of 2-Isopropenyl-2-oxazoline and Cross-linking Reaction of the Polymers

Kagiya

Matsuda

1972

Polym J

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ABSTRACT:The selective polymerization of 2-isopropenyl-2-oxazoline possessing two polymerizable sites in molecule was studied. Due to a marked difference in .polymerizability between the isopropenyl and oxazoline groups, this monomer provided soluble linear polymers by radical and cationic polymerization. The former was poly(2-isopropenyl-2-oxazoline) with the oxazoline group as a side chain, and the latter N-methacryloyl polyethylenimine. The cross-linking reactions of reactive pendant groups in both polymers, which resulted from the radical and cationic polymerizations, gave cross-linked, insoluble products.KEY WORDS Difunctional Monomer / 2-Isopropenyl-2-oxazoline / Selective Polymerization/ Poly(2-isopropenyl-2-oxazoline) / N-Methacryloyl Polyethylenimine / Cross-linking Reaction / Gelation / 2-Isopropenyl-2-oxazoline is a difunctional monomer possessing an isopropenyl group and oxazoline heterocycle as the polymerizable sites in molecule. It is reported by T. Kagiya, et al.,1 and several other investigators 2 -5 that 2-oxazolines can be polymerized by cationic catalysts such as stannic chloride or boron trifluoride etherate to give N-acyl or N-aryloyl polyethylenimine. Kagiya, et al.,6 reported that 2-isopropenyl-2-oxazoline gave poly(2-isopropenyl-2-oxazoline) by radical vinyl polymerization.The purpose of this paper is to report the selective cationic and radical polymerization of 2-isopropenyl-2-oxazoline, and the cross-linking reaction of the linear polymer having a polymerizable functional group as pendant side chain. EXPERIMENT AL MaterialN-Methacryloylethylenimine was prepared from the Schotten-Baumann reaction of ethylenimine and methacryloyl chloride in acetone media at -30°C, according to the method of Watanabe, et al. 7 2-Isopropenyl-2-oxazoline (IPOZ) was obtained from the isomerization reaction of N-methacryloylethylenimine with the use of sodium iodide as catalyst at 60°C for 15 hours according to the literature,8 and purified by careful distillation under reduced pressure [bp 50.5°C (17.5 mm)]. The identification was carried out by the infrared and NMR spectra of the product.Adipic acid as a cross-linker and a,a'-azobisisobutyronitrile (AIBN), which were commercially available products (G. R. Grade reagents), were used without further purification. Oxazolinium PerchloratePerchloric acid (70-% aqueous solution) ought not to be used as an initiator in the cationic polymerization of 2-oxazolines, because 2-oxazolines can be readily hydrolyzed. 9 The oxazolinium perchlorates of 2-isopropenyl-2-oxazoline and 2-phenyl-2-oxazoline as cationic initiators were prepared in the same manner as previously described. 11 The perchlorate salt of poly(2-isopropenyl-2-oxazoline) (Poly-IPOZ) was prepared by the same manner as above. From the elementary analysis and infrared spectrum, the following polyfunctional oxazolinium perchlorates were identified. Perchlorate salt of 2-isopropenyl-2-oxazoline (IPOZ-HC1O 4), mp 98.5-99.0°C.

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Section: Oxazolinium Perchloratementioning

confidence: 99%

Selective Polymerization of 2-Isopropenyl-2-oxazoline and Cross-linking Reaction of the Polymers

Kagiya

Matsuda

1972

Polym J

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“…It is well known that the reaction of 2-oxazolines with carboxylic acids, thiols and phenols leads to esteramides [17][18][19] , thioetheramides 20,21) and etheramides 22,23) . The synthesis of linear poly(ether amide)s in melt and solution of monomers containing one 2-oxazoline and one phenolic group was described by Mülhaupt et al 24) .…”

Section: Introductionmentioning

confidence: 99%

New hyperbranched poly(ether amide)s via nucleophilic ring opening of 2-oxazoline-containing monomers

Huber¹,

Böhme²,

Komber³

et al. 1999

Macromol. Chem. Phys.

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SUMMARY: An AB 2 monomer containing one oxazoline and two phenolic units was synthesized. The polymerization of the monomer 2-(3,5-dihydroxyphenyl)-1,3-oxazoline in N-methylcaprolactam resulted in a well-defined and fully soluble, high molar mass, hyperbranched polymer with etheramide structure. The hydrolysis of some oxazoline groups as side reaction limits the achieved molar mass when the polymerization is carried out in tetramethylene sulfone or in bulk. The polymers were characterized by one (1D) and two (2D) dimensional 1 H and 13 C NMR spectroscopy which allowed to determine the degree of branching to be 50% as expected from statistics. DSC and TGA measurements revealed a glass transition temperature of 176 8C and a decomposition onset of 330 8C. The thermal ring-opening reaction was studied in situ by DSC measurements.

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“…1) and the carboxyl content decreased, suggesting that reaction 3 took place. From the literature, 35 we find that oxazolines react easily with carboxylic compounds, forming esteramide groups.…”

Section: Chain Extension With Only Pbomentioning

confidence: 99%

Chain extension of recycled poly(ethylene terephthalate) with 2,2?-(1,4-phenylene)bis(2-oxazoline)

Karayannidis

Psalida

2000

J. Appl. Polym. Sci.

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Oxazoline Ring-Opening

Cited by 78 publications

References 9 publications

Selective Polymerization of 2-Isopropenyl-2-oxazoline and Cross-linking Reaction of the Polymers

Selective Polymerization of 2-Isopropenyl-2-oxazoline and Cross-linking Reaction of the Polymers

New hyperbranched poly(ether amide)s via nucleophilic ring opening of 2-oxazoline-containing monomers

Chain extension of recycled poly(ethylene terephthalate) with 2,2?-(1,4-phenylene)bis(2-oxazoline)

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