Poly(amide urethane)s with functional/reactive side groups based on a bis-cyclic bio-based monomer/coupling agent

Keul, Helmut; Mommer, Stefan; Möller, Martin

doi:10.1016/j.eurpolymj.2012.10.024

Cited by 24 publications

(27 citation statements)

References 29 publications

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“…For instance, the group reacted thiolactone compound bearing allyl or acrylate groups, with a variety of amine compounds through the radical thiol‐ene or nucleophilic thiol‐Michael addition reactions to prepare various linear polymers simultaneously . After that, various polymer topologies such as graft, hyperbranched, cyclic, and so forth as well as polymers with various applications through the thiolactone chemistry have been accomplished …”

Section: Introductionmentioning

confidence: 99%

“…12,13 After that, various polymer topologies such as graft, hyperbranched, cyclic, and so forth as well as polymers with various applications through the thiolactone chemistry have been accomplished. [14][15][16][17][18][19][20][21][22][23][24] In 2015, Rudolph et al synthesized a versatile monomer namely, maleimide thiolactone that can undergo homo and copolymerization through the radical polymerization. The resulting polymers possessing pendant thiolactone group were in situ reacted with butylamine and methyl acrylate (MA) at room temperature to demonstrate the versatility of maleimide thiolactone group toward the aminolysis and subsequent thiol-Michael reactions.…”

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confidence: 99%

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Study on Post‐Polymerization Modification of Ring‐Opening Metathesis Polymers Involving Pendant Thiolactone Units

Baysak

Dağlar

Gunay

et al. 2018

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

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Two different oxanorbornene monomers were prepared and copolymerized with butyl‐functionalized oxanorbornene monomer through the ring‐opening metathesis polymerization. The resulting polymers were then subjected to the aminolysis reactions with propylamine (PA) in the presence of methyl acrylate (MA) to capture, in situ, the latent thiol. It was found that the polymer, in which the thiolactone unit is close to the polymer backbone, did not undergo an efficient aminolysis reaction even an excess amount of PA was utilized, while the other polymer, in which the thiolactone unit away from the polymer backbone, did efficiently undergo aminolysis reaction even PA was used in low amounts. Besides, a variety of primary amine compounds along with MA were reacted with the polymer, in which the thiolactone group away from the polymer backbone, to test their reactivity toward the aminolysis reactions. All modified polymers were characterized by using conventional instruments such as gel permeation chromatography, nuclear magnetic resonance, and differential scanning calorimetry. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 2145–2153

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Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

Study on Post‐Polymerization Modification of Ring‐Opening Metathesis Polymers Involving Pendant Thiolactone Units

Baysak

Dağlar

Gunay

et al. 2018

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

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“…[10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] The biomedical importance of thiolactones is predominantly due to the homocysteinilation of proteins, which is an important risk factor in the study of vascular diseases, such as atherosclerosis. 26 Homocysteinilation occurs when homocysteine thiolactone, a cyclic thioester of the non-protein α-amino acid homocysteine, reacts with the ε-amine group of lysine residues.…”

Section: Introductionmentioning

confidence: 99%

Computational Study and Kinetic Analysis of the Aminolysis of Thiolactones

et al. 2015

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The aminolysis of three differently α-substituted γ-thiolactones (C4H5OSX, X = H, NH2, and NH(CO)CH3) is modeled based on CBS-QB3 calculated free energies corrected for solvation using COSMO-RS. For the first time, quantitative kinetic and thermodynamic data are provided for the concerted path and the stepwise path over a neutral tetrahedral intermediate. These paths can take place via an unassisted, an amine-assisted, or a thiol-assisted mechanism. Amine assistance lowers the free energy barriers along both paths, while thiol assistance only lowers the formation of the neutral tetrahedral intermediate. Based on the ab initio calculated rate coefficients, a kinetic model is constructed that is able to reliably describe experimental observations for the aminolysis of N-acetyl-dl-homocysteine thiolactone with n-butylamine in THF and CHCl3. Reaction path analysis shows that for all conditions relevant for applications in polymer synthesis and postpolymer modification, an assisted stepwise mechanism is operative in which the formation of the neutral tetrahedral intermediate is rate-determining and which is mainly amine-assisted at low conversions and thiol-assisted at high conversions.

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“…The reactivity of an AA' type monomer bearing a thiolactone and an ethylene carbonate was explored by Keul et al [244]. This multi-functional coupler was synthesized from glycerol and homocysteine thiolactone, two bio-based building blocks.…”

Section: Thiolactonesmentioning

confidence: 99%