New dicyano-containing cyclopolymers having high stereoregularity derived from dimethacrylmalononitrile

Tsuda, Takashi; Mathias, Lon J.

doi:10.1021/ma00076a010

Cited by 21 publications

(11 citation statements)

References 10 publications

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“…A generally accepted assumption in this field is that equal reactivity of the two vinyl groups in the monomer is important to achieve efficient cyclization, and our group has mostly focused on the design and synthesis of symmetric monomers containing identical vinyl groups [9,10]. For instance, syntheses of various cyclopolymers from ether, malonitrile, and amine-linked acrylate dimers have been described.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and cyclopolymerization of a functional non-symmetric divinyl monomer

Dizman¹,

Mathias²

2007

Polymer

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A non-symmetric divinyl monomer with a terminal carboxylic acid functionality was readily synthesized from the reaction of ethyl α-hydroxymethylacrylate (EHMA) with maleic anhydride. The new monomer (EHMA-MA) was homopolymerized in both bulk and ethyl acetate using AIBN as an initiator to give cyclopolymers. The synthesis of the monomer and cyclopolymers were followed by 13 C NMR, 1 H NMR, and FTIR. 1 H NMR was also utilized to obtain the degree of cyclization of the polymers, which were found to be 95% or higher in all cases. The molecular weights of the cyclopolymers were around 40-60,000 g/mol as estimated by SEC. The cyclopolymers were thermally stable up to 150 o C. Although the cyclopolymers obtained were not water-soluble; they were soluble in aqueous 1M NaOH solution. In addition to the carboxylic acid functionality present, the cyclopolymers also had an ethyl ester and a lactone moiety. These functional groups were reacted with hexylamine to obtain a polymer with imide and amide moieties.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and cyclopolymerization of a functional non-symmetric divinyl monomer

Dizman¹,

Mathias²

2007

Polymer

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“…Earlier studies showed that α,α ′‐dimethylenepimelates, ether dimers of α ‐(hydroxymethyl)acrylates and dicyano‐containing diacrylates are excellent monomers for cyclopolymerization, giving high polymerization rates, high cyclization efficiencies, low polymerization shrinkages, and high thermal stabilities for the polymers 16, 17. Synthesis and cyclopolymerization of a series of 4,4‐disubstituted 1,6‐diene monomers with different substituents (COOR, CN, aryl, substituted aryl, COOH, halogen, C(O)NHR, C(O)NR 2 at 2,6 positions and H, COOH, COOR, CN, C(O)NHR, C(O)NR 2 , P(O)(OR) 2 , SO 2 R at 4,4‐positions) have been reported 18…”

Section: Introductionmentioning

confidence: 99%

Influence of Structure on Polymerization Rates and Ca‐Binding of Phosphorus‐Containing 1,6‐Dienes

Albayrak¹,

Bilgici²,

Avcı³

2007

Macro Reaction Engineering

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Photo‐ and thermal‐polymerizations of 4‐diethoxyphosphoryl‐2,4,6‐tris(ethoxycarbonyl)‐1,6‐heptadiene, 4,4‐bis(diethoxyphosphoryl)‐2,6‐bis(t‐butoxycarbonyl)‐1,6‐heptadiene and 4‐diethoxyphosphoryl‐4‐ethoxycarbonyl‐2,6‐bis(t‐butoxycarbonyl)‐1,6‐heptadiene monomers and their phosphonic and carboxylic acid derivatives were investigated to understand the effect of the cyclic monomer structure on their polymerization reactivity. A strong effect of the substituents at positions 2, 4 and 6 of the monomers on polymerization rate was observed. The polymerizability of the monomers was successfully correlated with the 13C NMR chemical shifts of the vinyl carbons. Conversion values were consistent with the Tg being a measure of the flexibility of a monomer. The monomers containing phosphonic acid groups were soluble in water and ethanol. The acidic nature of the aqueous solutions of these monomers is expected to give them etching properties, important for dental applications. The interaction of the acid monomers with hydroxyapatite was investigated using 13C NMR technique.

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“…Earlar-intramolecular propagation to give soluble lier studies showed that a,a-dimethylenepimecyclopolymers under appropriate conditions. 1 The lates, [2][3][4] ether dimers of a-hydroxymethylacrycyclopolymers obtained have many advantageous lates, [5][6][7][8] and malononitrile linked diacrylates, 9 properties such as high glass transition temperahaving the general formula shown in Figure 1, tures, excellent thermal stabilities, and less are excellent monomers for cyclopolymerization. shrinkage during polymerization than noncyclic Increasing electronegativity and bulkiness of X linear analogs.…”

Section: Introductionmentioning

confidence: 99%

Cyclopolymerization of amine-linked diacrylate monomers

Avcı

Haynes

Mathias

1997

J. Polym. Sci. A Polym. Chem.

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New dicyano-containing cyclopolymers having high stereoregularity derived from dimethacrylmalononitrile

Cited by 21 publications

References 10 publications

Synthesis, characterization, and cyclopolymerization of a functional non-symmetric divinyl monomer

Synthesis, characterization, and cyclopolymerization of a functional non-symmetric divinyl monomer

Influence of Structure on Polymerization Rates and Ca‐Binding of Phosphorus‐Containing 1,6‐Dienes

Cyclopolymerization of amine-linked diacrylate monomers

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