Supramolecular Nucleating Agents for Poly(butylene terephthalate) Based on 1,3,5‐Benzenetrisamides

Richter, Florian; Schmidt, Hans‐Werner

doi:10.1002/mame.201200034

Cited by 19 publications

(31 citation statements)

References 19 publications

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“…Such intriguing modifications of the supramolecular polymer properties upon subtle changes in the close environment of the hydrogen-bonded assembling units has also been observed for benzene-1,3,5-tricarboxamides (BTAs). 39 BTAs are ubiquitous synthons in supramolecular chemistry due to their structural simplicity, the predictable mode of association of the monomers into rod-like structures and important applications as gels, [40][41][42][43][44][45] liquid-crystalline materials, 21,40,41,[46][47][48][49][50][51][52][53] thin films with remnant polarization, 54 additives for polymers, [55][56][57][58] MRI agents, [59][60][61][62] chiral templates for Au NPs 63 and catalysts. [25][26][27][28][29] Meijer and colleagues have shown that the stability of the rod-like aggregates (or stacks) formed by BTAs bearing chiral methyl-alkyl side chains increases when the stereogenic center is closer to the amide functions.…”

Section: Introductionmentioning

confidence: 99%

Tuning the nature and stability of self-assemblies formed by ester benzene 1,3,5-tricarboxamides: the crucial role played by the substituents

et al. 2016

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As the benzene 1,3,5-tricarboxamide (BTA) moiety is commonly used as the central assembling unit for the construction of functionalized supramolecular architectures, strategies to tailor the nature and stability of BTA assemblies are needed. The assembly properties of a library of structurally simple BTAs derived from amino dodecyl esters (ester BTAs, 13 members) have been studied, either in the bulk or in cyclohexane solutions, by means of a series of analytical methods (NMR, DSC, POM, FT-IR, UV-Vis, CD, ITC, high-sensitivity DSC, SANS). Two types of hydrogen-bonded species have been identified and characterized: the expected amide-bonded helical rods (or stacks) that are structurally similar to those formed by BTAs with simple alkyl side chains (alkyl BTAs), and ester-bonded dimers in which the BTAs are connected by means of hydrogen bonds linking the amide N-H and the ester C[double bond, length as m-dash]O. MM/MD calculations coupled with simulations of CD spectra allow for the precise determination of the molecular arrangement and of the hydrogen bond pattern of these dimers. Our study points out the crucial influence of the substituent attached on the amino-ester α-carbon on the relative stability of the rod-like versus dimeric assemblies. By varying this substituent, one can precisely tune the nature of the dominant hydrogen-bonded species (stacks or dimers) in the neat compounds and in cyclohexane over a wide range of temperatures and concentrations. In the neat BTAs, stacks are stable up to 213 °C and dimers above 180 °C whilst in cyclohexane stacks form at c* > 3 × 10 M at 20 °C and dimers are stable up to 80 °C at 7 × 10 M. Ester BTAs that assemble into stacks form a liquid-crystalline phase and yield gels or viscous solutions in cyclohexane, demonstrating the importance of controlling the structure of these assemblies. Our systematic study of these structurally similar ester BTAs also allows for a better understanding of how a single atom or moiety can impact the nature and stability of BTA aggregates, which is of importance for the future development of functionalized BTA supramolecular polymers.

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Section: Introductionmentioning

confidence: 99%

Tuning the nature and stability of self-assemblies formed by ester benzene 1,3,5-tricarboxamides: the crucial role played by the substituents

et al. 2016

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“…Recently this class of supramolecular building blocks was reviewed by Palmans et al 1,3,5‐Benzenetrisamides are accessible with a few synthetic steps and their structure can be tailored for a broad range of applications including nanotechnology, polymer additives, and biomaterials. Benzenetrisamides can be applied, for example, as nucleating agents for poly(vinylidene fluoride), poly(butylene terephthalate) (PBT), poly(ethylene‐ co ‐propylene), polylactides, and isotactic poly(propylene) ( i ‐PP) . In some cases trisamides are also efficient clarifiers .…”

Section: Resultsmentioning

confidence: 99%

Melt Electrospinning of Small Molecules

Singer

Ringk

Giesa

et al. 2015

Macro Materials & Eng

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Electrospinning is an attractive way to prepare nano‐ and macrofibers. It was demonstrated by our group that trisamides can be melt electrospun into supramolecular fibers. To establish structure–property relationships regarding spinnability and morphology, melt electrospinning experiments were conducted using several classes of compounds. The number of hydrogen bonds was systematically decreased from three for trisamides, to two for bisamide and sorbitols, and to zero for perylene bisimides and tertiary trisamides. As a result, trisamides are readily spun into fibers, whereas for bisamides and sorbitols mainly electrospraying into spheres is observed. Perylene bisimides form well‐defined fibers due to strong π–π interactions. This supramolecular fiber is interesting for many scientific disciplines.

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“…The physical and chemical properties of semi-crystalline polymers depend on their crystal structure and spherulite size to a large extent, both of which can be controlled by the addition of a nucleating agent into the polymer [4]. Isotactic polypropylene (iPP) is one of the most important thermoplastics with multifunctional characteristics [5].…”

Section: Introductionmentioning

confidence: 99%

Properties and Crystallization Behaviors of Isotactic Polypropylene Under Action of an Effective Nucleating Agent

Zhang

Guo

Chen

et al. 2015

Journal of Macromolecular Science, Part B

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The calcium salt of hexahydrophthalic acid (Hyperform HPN-20E) is an effective nucleating agent for polyethylene (PE) which was developed by Milliken Chemical Co., (U.S.A) in recent years. In this paper the properties and crystallization behaviors of isotactic polypropylene (iPP) in the presence of Hyperform HPN-20E were investigated by using differential scanning calorimetry (DSC) and polarized optical microscopy (POM). Addition of Hyperform HPN-20E improved the tensile, flexural and optical properties of iPP significantly and increased the crystallization rate of iPP greatly. The nucleation effects were comparable to the nucleation efficiency of a highly effective commercial iPP nucleating agent Hyperform HPN-68. When the addition amount of Hyperform HPN-20E in iPP was 0.2wt%, the tensile strength, tensile modulus, flexural strength and flexural modulus of iPP were increased by 10.81%, 8.65%, 16.67% and ACCEPTED MANUSCRIPT ACCEPTED MANUSCRIPT 2 11.96%, respectively, compared to those of pure iPP; the haze value was decreased by 42.44% and the crystallization peak temperature was increased by 11.2°C. In addition, incorporation of Hyperform HPN-20E in iPP greatly reduced the spherulite size of iPP.

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Supramolecular Nucleating Agents for Poly(butylene terephthalate) Based on 1,3,5‐Benzenetrisamides

Cited by 19 publications

References 19 publications

Tuning the nature and stability of self-assemblies formed by ester benzene 1,3,5-tricarboxamides: the crucial role played by the substituents

Tuning the nature and stability of self-assemblies formed by ester benzene 1,3,5-tricarboxamides: the crucial role played by the substituents

Melt Electrospinning of Small Molecules

Properties and Crystallization Behaviors of Isotactic Polypropylene Under Action of an Effective Nucleating Agent

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