The formation of poly(ester–urea) networks in the absence of isocyanate monomers

Zimmermann, Jörg; Loontjens, Ton; Scholtens, Boudewijn J. R.; Mülhaupt, Rolf

doi:10.1016/j.biomaterials.2003.09.110

Cited by 37 publications

(26 citation statements)

References 12 publications

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“…13.3) became available to produce caprolactam-blocked isocyanates, polyurethanes, and polyureas, as well as polyester urethanes and polyester ureas in melt phase reactions [13][14][15][16]. Novel chain extenders are becoming available which facilitate the controlled formation of molecular architectures with tailored property profiles.…”

Section: Reactive Extrusion and Isocyanate-free Polyurethane Chemistrymentioning

confidence: 99%

New Resins and Nanosystems for High‐Performance Adhesives

Mülhaupt

2005

Adhesion

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Recent advances in polymer sciences and nanotechnology are stimulating the development of adhesive with unusual property profiles. New catalyst systems and controlled polymerization processes afford unprecedented control of molecular and supermolecular architectures. Single site catalyst technology is the key to tailor-made polyolefins ranging from functional waxes and tackifiers to hot melt adhesives. Biocatalysis is claiming an increasing role in production of functional polymers. Advanced reactive extrusion processes exploit novel chain extender chemistry to produce block and graft copolymers as well as functionalized monomers and particles in solvent-free polymer extrusion processes. Carbonylbiscaprolactam is a new non-toxic additive which converts amines and hydroxyl groups into caprolactam blocked isocyanates without requiring the use of isocyanates or phosgene ("isocyanate-free polyurethane chemistry"). Nanophase separation and nanoparticle assembly improve the performance of flexible and structural adhesives. Epoxy adhesives based upon nanophase separated liquid rubber blends afford extraordinary crash resistance. The assembly of nanometer-scaled hyperbranched and dendritic polymers in bulk and at surfaces promotes both adhesion and cohesion. New families of nanocomposites based upon the assembly of organophilic nanoparticles such as silica, boehmite and layered silicates exhibit skeleton-like superstructures and afford the attractive combination of matrix reinforcement, high dimensional and environmental stabilities, improved toughness/stiffness balance, barrier resistance, halogen-free fire protection, tear resistance, and surface adhesion. Progress is highlighted by means of selected examples of new polymer intermediates and nanostructure formation.

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Section: Reactive Extrusion and Isocyanate-free Polyurethane Chemistrymentioning

confidence: 99%

New Resins and Nanosystems for High‐Performance Adhesives

Mülhaupt

2005

Adhesion

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“…As an example, N,N 0 -carbonylbiscaprolactam (CBC) is a commonly known chain extender first published in 1956 by Meyer [55]. Furthermore, Loontjens et al published studies using bislactams as chain extenders for a variety of polymers such as polyurethanes, polyamides, and polyesters [34,[56][57][58][59][60][61][62].…”

Section: Introductionmentioning

confidence: 99%

Impact of the chain extension of poly(ethylene terephthalate) with 1,3‐phenylene‐bis‐oxazoline and N,N′‐carbonylbiscaprolactam by reactive extrusion on its properties

Berg

Schaefer

Möller

2018

Polymer Engineering & Sci

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In this article, the material properties of chain extended poly(ethylene terephthalate) (PET) by application of the chain extenders, 1,3‐phenylene‐bis‐oxazoline (1,3‐PBO), N,N′‐carbonylbiscaprolactam (CBC), and combinations thereof are investigated aiming at an application during fiber production from postconsumer PET. The chain extension is performed in one step by a reactive extrusion process. The chain extenders are linearly linked to the COOH and/or OH terminal groups of PET. The influence of the chain extension on the properties of PET is analyzed by measurement of the inherent viscosity, size exclusion chromatography, and carboxyl end‐group titration. Furthermore, the impact of the chain extension on the thermal and rheological properties of PET is studied in detail by differential scanning calorimetry and rheology. The results demonstrate that chain extenders have impact on the properties of PET in dependence on their chemical composition and concentration. The improvement of the molecular weight of the obtained compounds is achieved in an effective and economical approach by the addition of small concentrations of chain extenders (0.2 wt% 1,3‐PBO or 0.3 wt% CBC) without significant negative impact on the properties of PET. POLYM. ENG. SCI., 59:284–294, 2019. © 2018 Society of Plastics Engineers

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“…To overcome these limitations, we studied an alternative methodology that circumvents the use of free isocyanates. Loontjens et al had shown that primary amines react quantitatively with carbonyl biscaprolactam (CBC), forming caprolactam BIs . Xiang and Asri et al have reported the synthesis of hyperbranched polyurea starting from AB 2 monomers prepared from a triamine and CBC and got biocompatible amphiphilic hyperbranched polyurea micelles and antibacterial‐coatings .…”

Section: Introductionmentioning

confidence: 99%

“…Loontjens et al had shown that primary amines react quantitatively with carbonyl biscaprolactam (CBC), forming caprolactam BIs. [33][34][35][36] Xiang and Asri et al have reported the synthesis of hyperbranched polyurea starting from AB 2 monomers prepared from a triamine and CBC and got biocompatible amphiphilic hyperbranched polyurea micelles and antibacterial-coatings. [37][38][39] Here, we report the synthesis and characterization of a novel diisocyanate, caprolactam blocked lysine diisocyanates methyl ester (BLDI-OMe), and the corresponding linear and crosslinked PUs.…”

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confidence: 99%

Lysine‐based functional blocked isocyanates for the preparation of polyurethanes provided with pendant side groups

Yin

Wildeman

Loontjens

2015

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

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This article describes a methodology to prepare polyurethanes (PUs), decorated with pendant (bio)functional side groups, by polymerizing (bio)functionalized blocked diisocyanates with polyols. Caprolactam blocked lysine diisocyanate methyl ester (BLDI-OMe) was prepared in high yields, by reacting the methyl ester of lysine with carbonyl biscaprolactam. In the absence of a catalyst, the polymerization of BLDI-OMe with polycaprolactone and polytetrahydrofuran resulted in strictly linear PUs due to the high selective reactivity of the blocked isocyanates (BIs). Although the ester appeared to be less reactive, we found hydrolyzing conditions for the ester, without affecting the BIs. The free acid groups were converted into a N-hydroxysuccinimide (NHS) activated ester, which was a versatile intermediate for further functionalization. After having demonstrated that model amines were able to substitute NHS without effecting the BIs groups, the same chemistry was used to couple biotin, giving a biotin functional caprolactam blocked lysine diisocyanate. The polymerization with polyols afforded the corresponding biotin-functional PUs.

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The formation of poly(ester–urea) networks in the absence of isocyanate monomers

Cited by 37 publications

References 12 publications

New Resins and Nanosystems for High‐Performance Adhesives

New Resins and Nanosystems for High‐Performance Adhesives

Impact of the chain extension of poly(ethylene terephthalate) with 1,3‐phenylene‐bis‐oxazoline and N,N′‐carbonylbiscaprolactam by reactive extrusion on its properties

Lysine‐based functional blocked isocyanates for the preparation of polyurethanes provided with pendant side groups

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