Aromatic polyamides by phosphorylation reaction with triphenylphosphite and LiCl in the presence of polymer matrix

Higashi, Fukuji; Taguchi, Yuji

doi:10.1002/pol.1980.170180911

Cited by 26 publications

(5 citation statements)

References 4 publications

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“…Luo et al measured a T g of 302 8C for the same furan PA with higher M n and M w . 38 Note, when we polymerize 4f using direct polycondensation using a Yamazaki-Higashi phosphorylation reaction, [58][59][60] the final product has its T g above the degradation temperature. 61 Furthermore, the T g of the p-phenylenediamine furan PA was higher than that of the m-phenylenediamine furan (256 8C) because para bonding creates additional rigidity.…”

Section: Thermal Properties Of the Pasmentioning

confidence: 99%

The effect of furan molecular units on the glass transition and thermal degradation temperatures of polyamides

Cureton

Napadensky

Annunziato

et al. 2017

J of Applied Polymer Sci

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Interfacial polymerization is used to prepare biobased furan polyamides from the carbohydrate‐derived monomer, 2,5‐furan dicarboxylic acid, aromatic diamines, and varying chain length aliphatic diamines. The molecular weights of the furan polyamides variations range 10,000–70,000 g/mol. These biobased polyamides have improved solubility relative to petroleum‐derived polyamides affording enhanced processability options. The glass transition temperatures (Tg) of the biobased furan polyamides are higher than that of aliphatic analogs, but lower than phenyl‐aromatic analogs. The Tg for these furan polyamides are as high as 280 °C. Also, the furan polyamide glass transition temperatures increase with decreasing aliphatic diamine chain length similar to results exemplified in petroleum‐based nylons. Group contribution parameters are determined for furans to enable simple prediction of the glass transition temperature and decomposition temperature of furan polyamides. The molar glass transition function for the furan is calculated to be 27.6 ± 1.5 K kg/mol. Thermal analysis measurements of the biobased furan polyamides have maximum thermal degradation temperatures at 350 °C or higher, similar to that of aliphatic polyamides when scaled with the number average molecular weight. The molar decomposition temperature functions are determined to be 37 K kg/mol for furans bonded to aliphatic units and 42 K kg/mol for furans bonded to phenyl units. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 45514.

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Section: Thermal Properties Of the Pasmentioning

confidence: 99%

The effect of furan molecular units on the glass transition and thermal degradation temperatures of polyamides

Cureton

Napadensky

Annunziato

et al. 2017

J of Applied Polymer Sci

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“…It was in 1969 that poly( m ‐benzamide), one of those polyamides, was first reported to be synthesized by the polycondensation of m ‐aminobenzoyl chloride 1. After that, the polymerization method has been improved: the polycondensation involving thioisocyanates2, 3 and isocyanate,4 and direct polycondensation from m ‐aminobenzoic acid,5–12 and so on. To add more solubility to the polymer, alkylation on the nitrogen of the amide linkage was also investigated 13.…”

Section: Introductionmentioning

confidence: 99%

A variety of poly(m‐benzamide)s with low polydispersities from inductive effect‐assisted chain‐growth polycondensation

Ohishi

Sugi

Yokoyama

et al. 2006

J. Polym. Sci. A Polym. Chem.

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Chain-growth polycondensation of 3-(alkylamino)benzoic acid alkyl esters 1 was investigated for obtaining poly(m-benzamide)s with defined molecular weights and low polydispersities. Polymerization conditions were first studied to find that ethyl 3-(octylamino)benzoate (1b) polymerized in a chain polymerization manner in the presence of lithium 1,1,1,3,3,3-hexamethyldisilazide (LiHMDS) as a base and phenyl 4-methylbenzoate (2b) as an initiator in THF at 0 8C. The molecular weight of the polymer was controlled by the feed ratio of monomer to initiator. The polymerization of 1c-i with a variety of N-alkyl groups was then carried out under the established conditions to yield well-defined poly(m-benzamide)s, which showed higher solubility than those of the corresponding poly(p-benzamide)s. Furthermore, the 4-octyloxybenzyl group on the amide nitrogen in poly1i was removed by treatment with trifluoroacetic acid (TFA) to give N-unsubstituted poly(m-benzamide) (poly1j) with a low polydispersity, which is soluble in DMAc and DMSO, contrary to the para-substituted counterpart. V V C 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 4990-5003, 2006The methyl ester monomer 1a was first polymerized with various bases in the presence of Scheme 1. Inductive effect-assisted chain-growth polycondensation of 1.POLY(m-BENZAMIDE)S WITH LOW POLYDISPERSITIES

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“…A complete separation of the daughter aramid from the polymer matrix could not be achieved for all samples. Indeed, it was always found that a relevant, and sometimes very large, amount of the polymer matrix could not be removed from the aramid, neither by solvent extraction of the matrix 12,14,15 nor by aramid dissolution and reprecipitation. As it was not possible to measure the intrinsic viscosity of the neat aramid, the intrinsic viscosity of the synthetic mixture (parent/ daughter pair) ([η] composite ) was measured.…”

Section: Resultsmentioning

confidence: 99%

“…To overcome this drawback, the effect of several polymer matrices in matrix polycondensation has been studied. In particular, poly(4-vinylpyridine) (P4VP), , poly(ethylene oxide), and poly(vinylpyrrolidone) (PVP) , have been successfully used. The above polymers are able to exert many simultaneous effects on the overall polymerization kinetics.…”

Section: Introductionmentioning

confidence: 99%

Poly(p-phenyleneterephthalamide)-Based Nanocomposites Obtained by Matrix Polycondensation. Synthesis and Solid-State NMR Characterization

et al. 2002

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Matrix polymerization can be viewed as an intriguing procedure for the preparation of homogeneous blends that are otherwise difficult or practically impossible to prepare. Poly(p-phenyleneterephthalamide) has been synthesized by direct polycondensation in the presence of poly(N-vinylpyrrolidone) or poly(4-vinylpyridine) as polymer matrices. The molecular weight effect of the latter polymers on the intrinsic viscosity of the aramid has been investigated. Poly(p-phenyleneterephthalamide), characterized by intrinsic viscosity as high as 14.2 dL/g, is obtained when high molecular weight poly-(N-vinylpyrrolidone) is used. The intimate composites formed in situ have been characterized by solidstate NMR. The parent and daughter polymers in the composite present the same proton T 1 relaxation times in the rotating frame, and this value differs from that of the neat polymers; this result demonstrates the intimacy of the blend at the level of a few nanometers.

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Aromatic polyamides by phosphorylation reaction with triphenylphosphite and LiCl in the presence of polymer matrix

Cited by 26 publications

References 4 publications

The effect of furan molecular units on the glass transition and thermal degradation temperatures of polyamides

The effect of furan molecular units on the glass transition and thermal degradation temperatures of polyamides

A variety of poly(m‐benzamide)s with low polydispersities from inductive effect‐assisted chain‐growth polycondensation

Poly(p-phenyleneterephthalamide)-Based Nanocomposites Obtained by Matrix Polycondensation. Synthesis and Solid-State NMR Characterization

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