Synthesis and radical polymerization of 2-vinylcyclopropanes

Moszner, Norbert; Völkel, Thomas; Zeuner, Frank; Rheinberger, Volker

doi:10.1002/1521-3900(200003)153:1<151::aid-masy151>3.0.co;2-h

Cited by 16 publications

(24 citation statements)

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“…Over the last 20 years, free radical ring-opening polymerization has been seen as a solution to the problem of polymerization volume shrinkage. Reports, [1][2][3][4][5][6][7][8][9][10][11][12][13][14] patents, [15][16][17][18] and reviews 19,20,21 in this field appear regularly in the literature, and a monograph 22 also has been published. Whereas much work continues on ketene acetal 23 and vinylcyclopropane derivatives, 24 we have developed novel cyclic allylic sulfide monomers such as the activated monomer 1 5,15,25 and the unactivated monomers 2-4.…”

Section: Introductionmentioning

confidence: 99%

“…1,3 Based on the new knowledge that substituents on the cyclic allylic sulfide monomers can give low polymerization shrinkage, we have now examined a series of methyl-substituted examples. Examples of six-, seven-, and eight-membered ring methylated derivatives (5)(6)(7)(8) were investigated as low shrink monomers. This series also allowed the examination of the effect of ring size on polymerizability.…”

Section: Introductionmentioning

confidence: 99%

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Free radical ring-opening polymerization of cyclic allylic sulfides: Liquid monomers with low polymerization volume shrinkage

Evans

Rizzardo

2000

J. Polym. Sci. A Polym. Chem.

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The free radical polymerization of four methylated cyclic allylic sulfides was examined with reference to their polymerization volume shrinkage and the effect of ring size on reactivity. The compounds examined were 2‐methyl‐5‐methylene‐1,3‐dithiane (5) (solid), 2‐methyl‐6‐methylene‐1,4‐dithiepane (6) (liquid), 6‐methyl‐3‐methylene‐1,5‐dithiacyclooctane (7) (liquid), and 6,8‐dimethyl‐3‐methylene‐1,5‐dithiacyclooctane (8) (liquid). The monomers were stable materials not requiring any special handling or storage conditions. They were polymerized in bulk using thermal azobisisobutyronitrile (AIBN, VAZO88) and photochemical initiators (Ciba DAROCUR 1173) and in benzene solutions (AIBN, 70 °C). The six‐membered ring monomer 5 was unreactive whereas seven‐membered ring monomer 6 polymerized to high conversion in bulk. In addition, 6 did not polymerize in benzene solution at 70 °C at [6] = 1.25M. Eight‐membered ring monomers 7 and 8 polymerized in bulk to complete conversion with thermal and photochemical initiators to give lightly crosslinked materials. Near complete conversion to soluble polymers could be obtained in solution polymerizations in benzene. Soluble polymers were also obtained in photochemical initiated bulk polymerizations by lowering initiator concentrations or length of irradiation. The methyl substituent had no effect on which allylic carbon–sulfur bond fragmented in the ring‐opening step. The polymerization volume shrinkages of monomers 7 and 8 were 1.5 and 2.4% respectively and together with monomer 4 (1.5–2.0% shrinkage) are the best available liquid free radical ring‐opening monomers that can be polymerized in bulk at room temperature. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 202–215, 2001

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Free radical ring-opening polymerization of cyclic allylic sulfides: Liquid monomers with low polymerization volume shrinkage

Evans

Rizzardo

2000

J. Polym. Sci. A Polym. Chem.

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“…Cyclopropanes bearing vinyl group (vinylcyclopropanes; VCP) undergo radical ring‐opening polymerization (RROP) to afford polymers with carbon–carbon double bonds in main chains and functional groups X and Y inherited from the monomers (Fig. ) . In the RROP process, the vinyl group of VCP reacts with radical species to give a carbon radical adjacent to the cyclopropane moiety.…”

Section: Introductionmentioning

confidence: 99%

“…1). [1][2][3][4][5][6][7][8][9][10] In the RROP process, the vinyl group of VCP reacts with radical species to give a carbon radical adjacent to the cyclopropane moiety. Then, the cyclopropane moiety undergoes the ringopening to afford acyclic radical species.…”

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confidence: 99%

Radical Ring‐Opening Polymerization Behavior of 1,1‐Dicyano‐2‐Vinylcyclopropane and Its Copolymerization with 1‐Cyano‐1‐Ester‐2‐Vinylcyclopropane

Okamoto

Sudo

Endō

2019

J. Polym. Sci. Part A: Polym. Chem.

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Radical ring‐opening polymerization of 1,1‐dicyano‐2‐vinylcyclopropane 1 was performed in benzonitrile to find the corresponding homopolymer 2 soluble in organic solvents was successfully obtained while that in other solvents gave crosslinked and thus insoluble homopolymer. In addition, 1 underwent radical copolymerization with 1‐cyano‐1‐ester‐2‐vinylcyclopropanes 3 and 4 to afford the corresponding copolymers 7 and 8. By increasing the content of the 1‐derived unit in the resulting copolymers, the solubility of the copolymers in organic solvents became lower and the residual weights at 600 °C and their glass transition temperatures became higher. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1723–1729

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“…[Unfortunately, an effective expanding polymerization for dental applications has yet to be developed; see (116).] Bone cements (Table 11.13) provide another example of composite materials being used in the biomedical field.…”

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confidence: 99%

Multicomponent Polymeric Materials

2005

Introduction to Physical Polymer Science

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Synthesis and radical polymerization of 2-vinylcyclopropanes

Cited by 16 publications

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Free radical ring-opening polymerization of cyclic allylic sulfides: Liquid monomers with low polymerization volume shrinkage

Free radical ring-opening polymerization of cyclic allylic sulfides: Liquid monomers with low polymerization volume shrinkage

Radical Ring‐Opening Polymerization Behavior of 1,1‐Dicyano‐2‐Vinylcyclopropane and Its Copolymerization with 1‐Cyano‐1‐Ester‐2‐Vinylcyclopropane

Multicomponent Polymeric Materials

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