Synthesis, Anisotropic Solutions, and Fibers of Poly(1,4-benzamide)

Kwolek, Stephanie L.; Morgan, Paul W.; Schaefgen, John R.; Gulrich, L. W.

doi:10.1021/ma60060a041

Cited by 337 publications

(141 citation statements)

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“…Oriented polymer fibres have been an important topic of research since the 1970s [3]. Successful commercial examples of high performance polymer fibres include ultra-high molecular weight polyethylene (UHMWPE) as commercialized under the name Dyneema ® [4] and aramid fibres as commercialized under the names Kevlar ® and Twaron ® [5]. The most commonly used methods of producing PLA fibres are melt spinning and solution spinning.…”

Section: Introductionmentioning

confidence: 99%

The Influence of Solid-State Drawing on Mechanical Properties and Hydrolytic Degradation of Melt-Spun Poly(Lactic Acid) (PLA) Tapes

Mai

Bilotti

et al. 2015

Fibers

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Abstract:The influence of solid-state drawing on the morphology of melt-spun poly(L-lactic acid) (PLLA) tapes, and the accompanying changes in mechanical and degradation behaviour have been studied. Mechanical properties are found to be strongly dependent on both applied draw ratio and drawing temperature. Moduli of these highly oriented tapes are significantly increased compared to as-extruded tapes at both ambient and elevated temperatures. Interestingly, drawing leads to a significant increase in elongation to break (~3 times) and toughness (~13 times) compared to as-extruded tapes. Structural and morphological characterization indicates strain-induced crystallization as well as an increase in orientation of the crystalline phase at small strains. Upon further stretching, an "overdrawing" regime is observed, with decreased crystalline orientation due to the breakage of existing crystals. For fixed draw ratios, a significant increase in Young's modulus and tensile strength is observed with increasing drawing temperature, due to a higher crystallinity and orientation obtained for tapes drawn at higher temperatures. FT-IR results indicate no crystal transformation after drawing, with the α-form being observed in all tapes. Hydrolytic degradability of PLLA was significantly reduced by solid-state drawing.

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Section: Introductionmentioning

confidence: 99%

The Influence of Solid-State Drawing on Mechanical Properties and Hydrolytic Degradation of Melt-Spun Poly(Lactic Acid) (PLA) Tapes

Mai

Bilotti

et al. 2015

Fibers

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“…In the original process the polycondensation is mediated by the reaction of amines with acid chlorides derived from the corresponding carboxylic acids in situ (depending on AB or AA/BB systems from the amino acid or diacid, respectively). 12 Moreover, polymerization techniques employing milder reagents have been developed over the past decades. Higashi and Yamazaki et al 13 as well as Ogata et al 14 examined the activation of the carboxylic acid moiety via active esters using phosphorusderived compounds (triphenylphosphite and triphenylphosphine, respectively).…”

Section: ■ Introductionmentioning

confidence: 99%

Bis-TEGylated Poly(p-benzamide)s: Combining Organosolubility with Shape Persistence

et al. 2013

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The synthesis of perfectly planar, bis-substituted aromatic polyamides is reported herein. With highly flexible triethylene glycol chains attached and conformational restriction through intramolecular, bifurcated hydrogen bonds these are among the most shape-persistent yet organo-soluble polymers to date. Starting from 4-nitrosalicylic acid, our group developed a route to phenyl-2,5-bis-TEGylated aminobenzoate, which could be polymerized by addition of lithium bis(trimethylsilyl)amide (LiHMDS). Since this technique has not been applied to step-growth polycondensations of polyaramides so far, the influence of two different solvents and an N-protective group was investigated. Therefore, substituted phenyl aminobenzoate derivatives carrying a free amine or an N-protective group have been polymerized. Additionally, the tendency for self-assembly of the readily soluble bis-TEGylated poly(p-benzamide) was observed by transmission electron microscopy (TEM) in the dried state. Dynamic light scattering (DLS) measurements of chloroform solutions did not indicate the formation of aggregates. Thus, intermolecular interactions, which other aromatic polyamides typically exhibit, are prevented. The access to bis-substituted, entirely rigid poly(p-benzamide)s via this new polycondensation method paves the way for exciting new structures in materials science and supramolecular chemistry.

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“…4-Amino-2-((2-ethylhexyl)oxy)benzoic acid (9) (1 g, 3.77 mmol) gave M6 as a transparent oil (390 mg, 0.904 mmol, 24% N-(2,4-Dimethoxybenzyl)aniline (DMB-aniline). Aniline (1 mL, 10.97 mmol) with 2,4-dimethoxybenzaldehyde (1.824 g, 10.97 mmol) were dissolved in DCM (27.4 mL, 0.4 M) and acetic acid (3.14 mL, 55 mmol) and stirred for 1 h. NaBH(CH 3 COO) 3 N-(4-Methoxybenzyl)aniline (PMB-aniline). Aniline (1 mL, 10.97 mmol) with 4-methoxybenzaldehyde (1.335 mL, 10.97 mmol) were dissolved in DCM (27.4 mL, 0.4 M) and acetic acid (3.14 mL, 55 mmol).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Aniline (1 mL, 10.97 mmol) with 4-methoxybenzaldehyde (1.335 mL, 10.97 mmol) were dissolved in DCM (27.4 mL, 0.4 M) and acetic acid (3.14 mL, 55 mmol). NaBH(CH 3 COO) 3 N-(2,4-Dimethoxybenzyl)-2-methoxyaniline (DMB-o-anisidine). 2-Methoxyaniline (9.16 mL, 81 mmol) with 2,4-dimethoxybenzaldehyde (13.49 g, 81 mmol) were dissolved in toluene (162 mL, 0.5 M) and refluxed under Dean−Stark conditions for 2 days until the amount of recovered water corresponded to the number of reactant equivalents (81 mmol, around 1.5 mL).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of High Molecular Weight Poly(p-benzamide)s

Badoux

Kilbinger

2017

Macromolecules

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The polymerization of aromatic para-amino acid ester derivatives was studied using model compounds. Mechanistic and kinetic experiments led to the discovery of some side reactions. Finally, high molecular weight poly(p-benzamide)s were synthesized and characterized. The use of highly reactive pentafluorophenol ester lead to polymers up to molecular weights of around 50 000 Da. Poly(benzamides) carrying both N-alkyl or N-benzyl groups on the amine could be polymerized to high molecular weight.

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Synthesis, Anisotropic Solutions, and Fibers of Poly(1,4-benzamide)

Cited by 337 publications

References 0 publications

The Influence of Solid-State Drawing on Mechanical Properties and Hydrolytic Degradation of Melt-Spun Poly(Lactic Acid) (PLA) Tapes

The Influence of Solid-State Drawing on Mechanical Properties and Hydrolytic Degradation of Melt-Spun Poly(Lactic Acid) (PLA) Tapes

Bis-TEGylated Poly(p-benzamide)s: Combining Organosolubility with Shape Persistence

Synthesis of High Molecular Weight Poly(p-benzamide)s

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