Polymer grafting onto polyurethane backbone via Diels-Alder reaction

Agar, Soykan; Durmaz, Hakan; Gunay, Ufuk Saim; Hızal, Gürkan; Tunca, Ümit

doi:10.1002/pola.27466

Cited by 15 publications

(13 citation statements)

References 24 publications

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“…When the network structure is further perfected, the effective movement segment becomes shorter. In the absence of solvent (Table ), the healing efficiency of L‐DAPU‐8 and C‐DAPU‐13 reaches 81.1 and 28.9%, respectively . The reason is that the compatibility of three components of L‐DAPU is good, but the compatibility of four components of the C‐DAPU is bad.…”

Section: Resultsmentioning

confidence: 99%

“…The additional advantage of D‐A cycloaddition in polymer chemistry is that thermal reversibility is utilized to synthesize thermoreversible materials. The functional polymer materials with ideal properties can be designed and synthesized, through the precise control of the polymer structure, which can polymerize at low temperature and depolymerize at high temperature …”

Section: Introductionmentioning

confidence: 99%

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Relationship on structure and properties of polyurethane modified Diels–Alder addition polymer

Liu

et al. 2018

J of Applied Polymer Sci

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A series of linear and crosslinked polyurethane modified materials were prepared by Diels-Alder cycloaddition reaction. Based on raw materials, some novel equations were designed and effects of equation parameters on the mechanical properties of modified material were explored. It was demonstrated that tensile strength of modified materials and elongation at break were changed from 3.68 to 18.71 MPa, 200 to 866%, respectively. In addition, the optimal reaction temperature of retro-Diels-Alder (r-DA) reaction was determined by differential scanning calorimeter (DSC). Gel permeation chromatography (GPC) and tensile experiments were used to characterize the properties of repolymerized material after degradation. The results indicated the optimal temperature of r-DA for linear and crosslinked polyurethane modified materials is 127 and 150 C. Moreover, after decomposed, the product was slowly repolymerized at 60 C, and can more effectively restore material strength under the action of the solvent to achieve self-healing effect.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Relationship on structure and properties of polyurethane modified Diels–Alder addition polymer

Liu

et al. 2018

J of Applied Polymer Sci

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“…With regard to step‐growth polymers, both postfunctionalization and functional monomer approaches have been put to use to obtain a range of azido‐functionalized aliphatic and aromatic polymers. The prominent examples of such polymeric systems include polycarbonates, polyesters, polyurethanes, polyamides, poly(ether sulfone)s, and poly(ether ether ketone)s . As far as functional monomer approach is concerned, most of the reports deal with aliphatic polymers and relatively lesser attention has been paid to monomers suitable for the synthesis of aromatic step‐growth polymers …”

Section: Introductionmentioning

confidence: 99%

A new cardo bisphenol monomer containing pendant azido group and the resulting aromatic polyesters

Maher

Nagane

Jadhav

et al. 2019

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

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Expanding on our strategy to synthesize aromatic stepgrowth polymers containing pendant clickable azido groups via functional monomer approach, we have now designed and synthesized a new cardo bisphenol, viz., 2-(2-azidoethyl)-3, 3-bis(4-hydroxyphenyl) isoindolin-1-one (PPH-N 3 ). PPH-N 3 was conveniently synthesized starting from commercially available phenolphthalein by a three-step route in an overall yield of 65% using simple organic transformations. Aromatic (co)polyesters bearing pendant azido groups were synthesized by low-temperature solution polycondensation of PPH-N 3 or different molar ratios of PPH-N 3 and bisphenol-A (BPA) with aromatic diacid chlorides in dry dichloromethane in the presence of triethylamine (TEA) as a base. The formation of medium to reasonably high-molecular-weight (co)polyesters was evidenced from intrinsic viscosity and number-average molecular-weight measurements that were in the range 0.52-0.85 dL/g and 16,700-28,200, respectively. Tough, transparent, and flexible films could be cast from chloroform solutions of these (co)polyesters. (Co)polyesters were characterized using FTIR, 1 H NMR, 13 C NMR spectroscopy, XRD, and TGA. The thermal curing reaction of (co)polyesters involving decomposition of azido groups was studied by DSC analysis. The chemical modification of a representative copolyester containing pendant azido groups was carried out quantitatively using catalyst-free azide-maleimide cycloaddition reaction with two maleimides, namely, Nmethylmaleimide and N-hexylmaleimide.Additional supporting information may be found in the online version of this article.

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“…CuAAC reactions have gained prevalent utilization in polymer science and have been employed in fabrication and functionalization of diverse polymeric materials [6][7][8][9][10][11][12][13][14][15][16][17]. Diels-Alder reactions constitute another important click methodology that proceeds under metal catalyst-free reaction conditions and the reaction kinetics are usually controlled with thermal effects [18][19][20][21][22][23][24][25]. This atom economic cycloaddition-based click approach has found widespread applications in synthesis of various macromolecular constructs [18,23,[26][27][28][29][30][31].…”

Section: Introductionmentioning

confidence: 99%

Click Chemistry in Macromolecular Design: Complex Architectures from Functional Polymers

Arslan

Taşdelen

2018

Chemistry Africa

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This contribution reviews the applications of click chemistry reactions in design and synthesis of various macromolecular architectures that hold key aspects in polymer science. By considering the emerging concepts that shape how synthetic polymer chemistry and macromolecular engineering utilize 'reactions' in 'fabrication', in the last decade, the click chemistry methodologies have been pioneered the chemical approaches that allow to access diverse complex macromolecules. The common and leading features of click chemistry reactions rely on efficient, fast, selective and easy to implement chemical transformations giving very high to quantitative coupling efficiencies. These are essential virtues that provide triumphing in macromolecular engineering, since the building blocks are usually large polymer chains. For the efficient building of complex macromolecules via click reactions, properly functionalized polymers are key components in which special design is required to successful installation of 'clickable' reactive groups on polymer end groups or side chains. In this report, the synthetic methods encompassing various click chemistry reactions in fabrication and applications of a range of complex macromolecular architectures have been reviewed.

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Polymer grafting onto polyurethane backbone via Diels-Alder reaction

Cited by 15 publications

References 24 publications

Relationship on structure and properties of polyurethane modified Diels–Alder addition polymer

Relationship on structure and properties of polyurethane modified Diels–Alder addition polymer

A new cardo bisphenol monomer containing pendant azido group and the resulting aromatic polyesters

Click Chemistry in Macromolecular Design: Complex Architectures from Functional Polymers

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