Synthesis and properties of new semifluoroalkylene-containing aromatic-aliphatic polyamides derived from aromatic diamines and semifluoroaliphatic dicarboxylic acids

Yoneyama, Mitsuru; Yamazaki, Kaori; Kakimoto, Masa–aki; Imai, Yoshio

doi:10.1002/(sici)1521-3935(19991001)200:10<2208::aid-macp2208>3.0.co;2-p

Cited by 3 publications

(2 citation statements)

References 11 publications

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“…HDITF has lower transition temperatures than HDIBD. This is in good agreement with the previous studies by many investigators20–22 in which the fluorine‐containing polyamides had lower melting temperatures than the corresponding fluorine‐free polyamides. This might be attributed to the disruption of polymer chain packing by the introduction of the fluorocarbon chains, as observed in FTIR analysis.…”

Section: Resultssupporting

confidence: 93%

“…On the contrary, HDIBD is only soluble in DMAc, DMF, and DMSO above a temperature of about 45, 70, and 45°C, respectively. The solubility behavior clearly indicates that the introduction of (CF 2 ) 2 moieties apparently improved the solubility of the polyurethane, due to the disruption of polymer chain packing, as is often the case for fluorine‐containing polyamides 20–22…”

Section: Resultsmentioning

confidence: 78%

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Influence of fluorocarbon chains on the crystallization behaviors of aliphatic polyurethanes

Chen

Kuo

2008

J of Applied Polymer Sci

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The aliphatic polyurethanes were synthesized from either hexamethylene diisocyanate (HDI) and 2,2,3,3-tetrafluoror-1,4-butanediol or HDI and 1,4-butandiol. The crystallization behaviors of the aliphatic polyurethanes were characterized using differential scanning calorimetry, wide-angle X-ray diffraction, and polarized optical microscopy. The effects of fluorocarbon chains on the solubility behavior, microstructure, thermal transition property, crystal morphology, and crystallization behaviors were investigated. The fluorinated polyurethane exhibited a lower viscosity, higher solubility in organic solvents, smaller fraction of ordered hydrogen-bonded carbonyls, and lower transition temperatures than the corresponding fluorine-free polyurethane. The wideangle X-ray diffraction measurements reflected change of crystal structure with the (CF 2 ) 2 moieties in place of (CH 2 ) 2 moieties. Polarized optical microscopy also revealed that the polyurethanes exhibited a variety of spherulitic texture. The isothermal crystallization process of the polyurethanes was described by the Avrami analysis. The result showed that the Avrami exponent (n) was around 2.5, which suggested the growth of crystal might be spherulite growth corresponding to homogeneous (thermal) nucleation and diffusion control. The crystallization activation energy was estimated to be À130.9 kJ/ mol for the fluorinated polyurethane and À276.9 kJ/mol for the fluorine-free polyurethane from Arrhenius form.

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Section: Resultssupporting

confidence: 93%

Section: Resultsmentioning

confidence: 78%

Influence of fluorocarbon chains on the crystallization behaviors of aliphatic polyurethanes

Chen

Kuo

2008

J of Applied Polymer Sci

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Synthesis and characterization of novel, optically active polyamides derived from S-valine natural amino acid and bulky anthracenic side chain

Mallakpour

Mirkarimi

2010

Amino Acids

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This is the first description of the application of molten tetrabutylammonium bromide (TBAB) in the presence of triphenyl phosphite (TPP) for the synthesis of novel polyamides (PAs). Monomer diacid, 5-[(9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximido)-3-methylbutanoylamino]isophthalic acid (4), having anthracenic and amino acid S-valine pendant group, was synthesized in four steps. Several novel, optically active PAs were prepared by the condensation of synthesized diacid monomer 4 with various aromatic diamines using two different techniques: a mixture of N-methyl-2-pyrrolidone (NMP)/TPP/pyridine/calcium chloride (method I) and combination of TPP with TBAB (method II). The main goal of the present paper was to prepare novel PAs in a green media by removal of toxic reagents. Therefore, TBAB/TPP was used as a novel, easy, safe and eco-friendly method for the preparation of aromatic PAs. This method is compared with the polymerization reaction under conventional solvent and in the case of TBAB as a new method, higher yields, inherent viscosities and thermally stable of PAs are gained. The resulting polymers showed good solubility in polar aprotic solvents such as dimethyl sulfoxide, NMP, N,N-dimethylacetamide and N,N-dimethylformamide. These polymers are characterized with respect to chemical structure and purity by means of specific rotation experiments, FT-IR, 1H NMR spectroscopy techniques and elemental analysis. The obtained PAs exhibit good thermal stability up to 335°C for 10% weight loss in nitrogen atmosphere and glass transition temperatures fell in the rang of 177-185°C.

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Synthesis of fluorinated telechelics as precursors of well-defined fluoropolymers

Améduri¹,

Boutevin²

2004

Well-Architectured Fluoropolymers: Synthesis, Properties and Applications

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Synthesis and properties of new semifluoroalkylene-containing aromatic-aliphatic polyamides derived from aromatic diamines and semifluoroaliphatic dicarboxylic acids

Cited by 3 publications

References 11 publications

Influence of fluorocarbon chains on the crystallization behaviors of aliphatic polyurethanes

Influence of fluorocarbon chains on the crystallization behaviors of aliphatic polyurethanes

Synthesis and characterization of novel, optically active polyamides derived from S-valine natural amino acid and bulky anthracenic side chain

Synthesis of fluorinated telechelics as precursors of well-defined fluoropolymers

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