Polyamides based on a partially bio-based spirodiamine

A new aromatic diacid, containing preformed diamide functional group, C8 alkylene moiety, and two methylene spacers, viz; N, N′‐bis(4′‐carboxy methylene phenyl) decane diamide (BCPDD) was designed and successfully synthesized. The structure of BCPDD was confirmed by FT‐IR, NMR (1H, 13C) spectroscopy and mass spectrometry. The corresponding series of new polyamides were prepared via reactions of diacid (BCPDD) and commercial aromatic diamines by Yamazaki's phosphorylative direct polycondensation method. Physical properties of these polyamides such as inherent viscosity, solubility in organic solvents, glass transition temperatures by DSC, thermal stability by TGA, and amorphous‐crystalline mature by XRD were studied. The incorporation of preformed amide, methylene spacers, and C8 alkylene moiety greatly affected polyamide properties such as solubility in common organic polar solvents, glass transition temperature, and thermal stability. These polyamides were mostly amorphous in nature and dissolved in polar aprotic solvents such as N‐methyl‐2‐pyrrolidone, N, N‐dimethylacetamide, N, N‐dimethylformamide, dimethyl sulfoxide, m‐cresol, and pyridine. Inherent viscosities of these polyamides were in the range of 0.40–0.67dL/g; indicating the formation of moderate to high molecular weights. These polyamides exhibited good thermal stability having temperatures for 10% weight loss (T10) in the range of 404–578°C and the char yields at 800°C in the range of 35–65%. The glass transition temperatures; as determined by DSC were in the range of 204–235°C.

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New polyamides based on diacid with decanediamide and methylene groups and aromatic diamines

Diwate

Tamboli

Ghodke

et al. 2022

“…From the FTIR spectra for PBAC2 shown in Figure , the characteristic amide and methylene absorption bands appear at: 3298 cm −1 (amide A), 2918 cm −1 (CH), 1654 cm −1 (amide I), 1509 cm −1 (amide II), 758 cm −1 (amide V) …”

Section: Resultsmentioning

confidence: 99%

Preparation, analysis, and isothermal crystallization behavior of poly[1,3‐bis(aminomethyl)cyclohexamethylene oxamide]

Mutua

Yang

Gao

et al. 2018

Poly[1,3-bis(aminomethyl)cyclohexaneoxamide] (PBAC2) was synthesized using 1,3-bis(aminomethyl)cyclohexane (BAC) and dibutyl oxalate (DO) via spray/solid-state polycondensation (SSP). The structure of the synthesized polyoxamide was confirmed by 1 H-nuclear magnetic resonance (NMR) and Fourier transform infrared spectroscopy. The weight average molecular weight (M w ) of the polyoxamides prepared was 1.35 3 10 5 . The polyoxamides showed excellent thermal properties with glass transition temperature (T g ) of 150 8C, melting temperature (T m ) of 318 8C, crystallization temperature(T c ) of 253 8C, and initial degradation temperature (T d ) of 417 8C suggesting higher thermal stability than commercial polyamide 6 (T d 5 378 8C). Kinetic studies of PBAC2 predicted a two-dimensional crystal growth. X-ray diffraction powder diffraction suggested that the polymer has high crystallinity. A saturated water absorption of 2.8 wt % was recorded for the new polyoxamide, giving it a competitive edge for applications in civil aviation, reinforced plastics, and electronics industry where precise dimensional stability and high thermal resistance properties are a priority.

“…Recently, due to the limited amount of fossil resources and the environmental issues, there have been many studies to obtain high‐performance aromatic polyamides derived from biomass‐based monomers 7,8 . Among those biomass‐based aromatic monomers, 2,5‐furandicarboxylic acid (FDCA) is produced by chemical or biological treatment of 5‐hydroxymethylfurfural (HMF) obtained from renewable glucose resources.…”

Section: Introductionmentioning

confidence: 99%

Phosphorylation‐assisted synthesis and characterization of poly(3,4'‐oxydiphenylene furanamide) as a wholly aromatic polyamide using biomass‐derived 2,5‐furandicarboxylic acid

Choi

Jeong

2022

We report the phosphorylation‐assisted polymerization and characterization of 2,5‐furandicarboxylic acid (FDCA)‐based wholly aromatic polyamide. For this purpose, poly(3,4′‐oxydiphenylene furanamide) (PODFA) was synthesized via solution polymerization of FDCA with 3,4′‐oxydiphenylamine (ODPA) in the presence of triphenyl phosphite and pyridine. The spectroscopic analyses and solution viscosity measurement revealed the successful synthesis of a relatively high molecular weight PODFA with good solubility in a variety of polar aprotic solvents without inorganic salts. PODFA could be thus processed into purely amorphous films with high flexibility in bending and folding deformation. The 39 μm thick PODFA film exhibited optical transparency, and the 65–100 μm thick films showed a transparent yellow or light brown color. The amorphous PODFA films were characterized to have excellent thermal and static mechanical properties in terms of a glass transition temperature of ~260°C, a thermal decomposition peak temperature of ~450°C, a residue of ~50% at 800°C under nitrogen gas condition, an initial modulus of 12.98 ± 1.84 GPa, a tensile strength of 84.6 ± 17.3 MPa, and a strain at break of 2.3 ± 1.5% at room temperature.