A novel multifunctional coupler: the concept of coupling and proof of principle

Mommer, Stefan; Lamberts, Kevin; Keul, Helmut; Möller, Martin

doi:10.1039/c3cc40369f

Cited by 25 publications

(21 citation statements)

References 14 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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“…Bis(thiolactone) 14 reacts similar to the polyepoxides via ring opening of the five‐membered cycles. Nucleophiles provoke lysis of the thiolactone, which is in a strained ring conformation and an active ester at the same time . Upon ring‐opening of the cycle, free thioethyl moieties are released that further support the crosslinking process via atmospheric oxidation of the thiols to disulfide bonds .…”

Section: Resultsmentioning

confidence: 99%

Formaldehyde‐free curing of cotton cellulose fabrics in anhydrous media

Mommer

Kurniadi

Keul

et al. 2019

J of Applied Polymer Sci

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The effect of formaldehyde-free curing on standard cotton cellulose fabrics in anhydrous media is studied. Different crosslinkers are applied via (1) a pad-cure-dry process (solid/liquid) and (2) in a vapor chamber (solid/gas). The performance of each crosslinker and set of conditions is assessed by measuring dry crease recovery angles, DCRAs. We find that in control samples (treatment without crosslinker) the DCRAs are altered depending on the solvent. Using DMF, carbonyldiimidazole shows the best DCRA (160.1 , 15 higher than the non-treated fabrics). In ethyl acetate, triglycidyl isocyanurate shows the highest DCRA (22 higher than the control). The most promising crosslinkers are applied with selected catalysts known from literature. Here, trigycidyl isocyanurate in combination with the superbase P4-t-Bu gives the best DCRA (35 higher than the control). Using the vapor-chemical finishing, divinylsulfone as crosslinker increases the DCRA to 162.7 (18 higher than non-treated fabrics). Hence, cotton cellulose fabrics can be successfully finished in anhydrous conditions.

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“…The homocysteine thiolactone moiety has been thoroughly investigated in regard to its reactivity with amines and subsequent thiol-ene reactions [29,30]. A bifunctional coupler with an ethylene carbonate and a thiolactone functionality was synthesized starting from either (2-oxo-1,3-dioxolan-4-yl)methyl phenyl carbonate or glycerol chloroformate (Scheme 2, J) [31,32]. Both functional groups were selectively addressed by an amine, dependent on the temperature, allowing the addition of two different amines.…”

Section: Methodsmentioning

confidence: 99%

Homoserine Lactone as a Structural Key Element for the Synthesis of Multifunctional Polymers

et al. 2017

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Abstract:The use of bio-based building blocks for polymer synthesis represents a milestone on the way to "green" materials. In this work, two synthetic strategies for the preparation of multifunctional polymers are presented in which the key element is the functionality of homoserine lactone. First, the synthesis of a bis cyclic coupler based on a thiolactone and homoserine lactone is displayed. This coupler was evaluated regarding its regioselectivity upon reaction with amines and used in the preparation of multifunctional polymeric building blocks by reaction with diamines. Furthermore, a linear polyglycidol was functionalized with homoserine lactone. The resulting polyethers with lactone groups in the side chain were converted to cationic polymers by reaction with 3-(dimethylamino)-1-propylamine followed by quaternization with methyl iodide.

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A novel multifunctional coupler: the concept of coupling and proof of principle

Cited by 25 publications

References 14 publications

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

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

Formaldehyde‐free curing of cotton cellulose fabrics in anhydrous media

Homoserine Lactone as a Structural Key Element for the Synthesis of Multifunctional Polymers

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