Synthesis of poly(urethane)s based on diphenyl‐silane/germane and oxyphenyl units: Structure–properties relationship

Tundidor‐Camba, Alain; Terraza, Claudio A.; Tagle, L. H.; Coll, Deysma; Ortiz, Pablo

doi:10.1002/app.35185

Cited by 14 publications

(13 citation statements)

References 13 publications

(14 reference statements)

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“…On the other hand, the PEAzMs derived from the 4‐isopropylphenoxy‐based diamine (PEAzM‐3 and PEAzM‐6) exhibited the highest transparencies of their respective series, in agreement with their lower chain‐packing forces in solution due to the higher volume of the isopropyl groups in comparison with the hydrogen and methyl substituents. Similar results have been reported for silylated‐polycondensation materials and not‐silylated polymers, such as fluorine‐containing semiaromatic poly(imide)s …”

Section: Resultssupporting

confidence: 86%

Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization

Tundidor‐Camba

Araya

González‐Henríquez

et al. 2019

J of Applied Polymer Sci

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Three new diamines derived from epoxide compounds were synthesized. The preparation of diamine monomers implied the reaction between a phenoxyalkyloxirane (alkyl: H, methyl, isopropyl) and bisphenol A, obtaining the respective aliphatic diols, which produced the corresponding dinitro derivatives. Finally, these derivatives were reduced by using palladium/carbon activated as catalyst and hydrazine as a hydrogen source. Then, six oligomeric poly(ether-azomethine)s (PEAzMs) were obtained from a polycondensation reaction between the new diamines and bis(4-formylbiphenyl-4-yl)dialkylsilane (alkyl: methyl, phenyl) with 84-93% yields. The structural characterization of the diamines and PEAzMs was performed by elemental analysis, infrared spectroscopy, and nuclear magnetic resonance spectroscopy ( 1 H, 13 C, and 29 Si). Furthermore, polymers were analyzed by solubility tests, gel permeation chromatography, ultraviolet-visible (UV-vis) spectroscopy, thermogravimetry, and differential scanning calorimetry analysis. The results showed PEAzMs with 2-11 repetitive units, where the design of the monomers allowed to obtain improved solution processability in comparison with previously reported silylated poly(azomethine)s and good thermal stability. Additionally, all samples showed high transparency in the UV-vis region.

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Section: Resultssupporting

confidence: 86%

Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization

Tundidor‐Camba

Araya

González‐Henríquez

et al. 2019

J of Applied Polymer Sci

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“…Figure 1 shows the synthetic scheme of both, the diacids and the PIAs. In particular, the 29 Si NMR spectra showed the signals corresponding to the Si atom bonded to four aromatic rings at -15 ppm approximately, which has been described for other monomers and polymers containing similar residues in the main chain (20). Table I shows the yields.…”

Section: Resultssupporting

confidence: 57%

Synthesis, Characterization and Thermal Studies of Wholly Aromatic Poly(imide-Amides) Containing Si and/or Ge in the Main Chain

Tagle

Terraza

Ortiz

et al. 2011

J. Chil. Chem. Soc.

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Poly(imide-amides) (PIAs) containing the heteroatoms Si and/or Ge in the main chain were obtained from diacids, which were synthesized from trimellitic anhydride and the diamines bis(4-aminophenyl)diphenylsilane or bis(4-aminophenyl)diphenylgermane. With the same diamines the polymers containing the heteroatoms Si and Ge in the main chain were obtained. Polymers were soluble in aprotic polar solvents and characterized by IR and 1 H, 13C and 29Si NMR spectroscopy, and the results were in agreement with the proposed structures. Low inherent viscosity values (h inh ) (0.04 -0.12 dL/g) were obtained, indicating the presence of oligomeric species. The Tg values were obtained by differential scanning calorimetry (DSC), and the results did not show a relation with the nature of the heteroatoms, in the sense that the polymers with Si should have higher Tg values than those with Ge due to the lower volume of the former atom. Also, the low values of h inh associated to low molecular weight species, have important influence on Tg values. The thermal decomposition temperatures were obtained by dynamic thermogravimetry. These analyses showed that the highest thermal decomposition temperature (TDT) values were obtained for PIA-II and PIA-III with Si and Ge in the repeating unit, and the lowest TDT values with two Si atoms in the unit.

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“…The NMR spectroscopic data are summarized in the Experimental Part. 29 Si NMR spectra showed in all PIAs a signal at about −15 ppm approximately, corresponding to the Si atom bonded to four aromatic rings, which has been described for our group in several other systems (22,23). Table 1 shows the solubility behavior of PIAs.…”

Section: Polymer Synthesismentioning

confidence: 66%

Synthesis of Oligomeric Silicon-containing Poly(imide-amide)s Derived from Trimellitic Anhydride and Amino-Acids. Vibration Spectral, Optical, Thermal and Morphological Characterization

Tagle

Terraza

Ortiz

et al. 2012

Journal of Macromolecular Science, Part A

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Poly(imide-amide)s (PIAs) were synthesized from diacids, which were obtained by trimellitic anhydride and glycine, L-alanine, Lphenylalanine, L-valine, L-leucine, L-isoleucine and p-aminobenzoic acid, and bis(4-aminophenyl)diphenylsilane. Compounds were characterized by elemental analysis, optical activity, IR and NMR spectroscopies. Yields were good, but η inh values were low, showing materials of oligomeric nature, confirmed by MALDI-TOF spectrometry. PIAs were soluble in polar aprotic solvents, while those derived from amino acids with bulky side groups were soluble in CHCl 3 and acetone. The wavenumber of vibrational bands were compared by Infrared and Raman spectroscopy. However, the high fluorescence emitted for PIAs, difficult to predict the vibrations of certain functional groups by Raman spectroscopy. The incorporation of chiral, amide and imide moieties interrupt the conjugation and increase the flexibility of the system. In addition, the adjacent phenyl units from the silicon-containing diamine, disfavors the planar conformation, which affects the optical properties showing an insulator behavior. DSC analyses showed that PIA-VII of aromatic nature had the higher glass transition temperature (Tg) value. For the other PIAs the Tg values decreased when volume of the side groups was increased, with the exception of PIA-VI derived from L-isoleucine. The thermal decomposition temperatures showed that only PIA-VII derived from p-aminobenzoic acid was thermostable. For the other PIAs it was possible to see a decrease of the TDT values when the size of the side chain is increased. The size and shape of the polymeric particles were studied by Scanning Electronic Microscopy (SEM), showing a relation between structure, incorporation of rigid aromatic rings and voluminous group into the system.

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Synthesis of poly(urethane)s based on diphenyl‐silane/germane and oxyphenyl units: Structure–properties relationship

Cited by 14 publications

References 13 publications

Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization

Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization

Synthesis, Characterization and Thermal Studies of Wholly Aromatic Poly(imide-Amides) Containing Si and/or Ge in the Main Chain

Synthesis of Oligomeric Silicon-containing Poly(imide-amide)s Derived from Trimellitic Anhydride and Amino-Acids. Vibration Spectral, Optical, Thermal and Morphological Characterization

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