Equilibrium ring‐opening polymerization of mono‐ and multicyclic unsaturated monomers

Ofstead, E. A.; Calderon, Nissim

doi:10.1002/macp.1972.021540102

Cited by 134 publications

(58 citation statements)

References 13 publications

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“…equilibrium concentration) was influenced only by the applied reaction temperature. 10 The thermodynamic parameters for the cyclopentene polymerization employing ruthenium-based complexes were calculated and found to be lower than those of achieved via tungsten catalyzed systems. Table 1).…”

Section: Resultsmentioning

confidence: 97%

Synthesis of Recyclable Tire Additives via Equilibrium Ring-Opening Metathesis Polymerization

Tuba

Balogh

Hlil

et al. 2016

ACS Sustainable Chem. Eng.

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ABSTRACT. Linear trans-polypentenamers are highly desired materials among the synthetic tire additives due to their comparable physical properties to natural rubber. Transpolypentenamer can be prepared by equilibrium ring-opening metathesis polymerization (ROMP) using well-defined ruthenium catalyst systems. This unique feature of the equilibrium polymerization reaction opens a way for the synthesis of durable, environmentally benign elastomers where polymers including synthetic tire additives can be synthesized and readily recycled using the same transition metal catalyst system. The addition of silica fillers significantly improves the physical properties of the composite materials in comparison to the use of polymeric material. It is also known that the structural effects and the polymer-filler surface interaction are of prime importance. Herein, we report on the synthesis of silica filler compatible recyclable polypentenamer co-polymers via equilibrium ROMP of cyclopentene 1 and 4-(triethoxy)siloxy cyclopentene 11. It has been demonstrated that polypentenamer tire additive can be synthesized via equilibrium ROMP affording polymers with high yields (> 80%) at 0 ºC and can be readily depolymerized at 40 ºC and/or under diluted condition using the same metathesis catalyst systems. Furthermore, the polypentenamer can also be synthesized in neat at room temperature and at very low (10 5 ) monomer/catalyst ratio. This methodology is based on the synthesis of polyolefins utilizing ruthenium based metathesis catalyst via equilibrium ROMP of cyclopentenes and their silylated derivatives.3

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Section: Resultsmentioning

confidence: 97%

Synthesis of Recyclable Tire Additives via Equilibrium Ring-Opening Metathesis Polymerization

Tuba

Balogh

Hlil

et al. 2016

ACS Sustainable Chem. Eng.

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“…Whereby, the monomer conversion is dependent on the reaction temperature and not the catalyst activity, resulting in a monomer-polymer equilibrium. 54,55 PIB Ru complex 8 was prepared following previously published protocols. The catalytic activity of complexes HG2 and 8 were evaluated for the equilibrium ROMP of monomer M4 at two different temperatures.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Polypentenamer and Poly(Vinyl Alcohol) with a Phase‐Separable Polyisobutylene‐Supported Second‐Generation Hoveyda–Grubbs Catalyst

et al. 2015

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Equilibrium ring opening metathesis polymerization (ROMP) of strained cyclic olefins using a soluble supported second generation Ru complex has been investigated. Cycloolefin homoand copolymers are of great academic and industrial importance due to their interesting applications as packaging materials, adhesives in coatings and optoelectronics. The supported complex exhibits good chemical stability and was effective in ROMP of strained cyclic olefins. In addition, the complex is easily phase separated from the product resulting in lower residual ruthenium in the final polymer product compared with the homogeneous complex.

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“…6 The thermodynamic study using WCl 6 /Al(C 2 H 5 )Cl 2 catalysts revealed that the cyclopentene conversion does not depend on the catalyst activity but the reaction temperature. 7 This observation indicated characteristic monomer-polymer equilibrium.…”

Section: Introductionmentioning

confidence: 86%

Ruthenium catalyzed equilibrium ring-opening metathesis polymerization of cyclopentene

2013

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Polypentenamer was synthetized by equilibrium ring-opening metathesis polymerization (ROMP) using well-defined ruthenium catalyst systems. It was found that the equilibrium time is influenced by the catalyst loading or the catalyst activity, however as expected, the overall cyclopentene conversion is determined only by the applied reaction temperature. Equilibrium of the growing chain and monomer was observed and the activation enthalpy and entropy were determined as: DH ¼ À5.6 kcal mol À1 ;. So far these values are the lowest which are reported for cyclopentene polymerization catalyst systems. This unique feature of the equilibrium polymerization opens a way for the synthesis of durable, environmentally friendly elastomers where tires can be not only synthetized but also readily recycled by the same transition metal catalyst system.

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Equilibrium ring‐opening polymerization of mono‐ and multicyclic unsaturated monomers

Cited by 134 publications

References 13 publications

Synthesis of Recyclable Tire Additives via Equilibrium Ring-Opening Metathesis Polymerization

Synthesis of Recyclable Tire Additives via Equilibrium Ring-Opening Metathesis Polymerization

Synthesis of Polypentenamer and Poly(Vinyl Alcohol) with a Phase‐Separable Polyisobutylene‐Supported Second‐Generation Hoveyda–Grubbs Catalyst

Ruthenium catalyzed equilibrium ring-opening metathesis polymerization of cyclopentene

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