Synthesis and viscosity behavior of poly(γ-p-biphenylmethyl-L-glutamate) in benzene/dichloroacetic acid mixtures, a comparison with poly(γ-benzyl-L-glutamate)

Jan Feijen, Wim L. Sederel, Klaas de Groot, Anthonie C. de Visser, Adriaan Bantjes

Research output: Contribution to journalArticleAcademic

41 Downloads (Pure)

Abstract

The synthesis of poly(γ-p-biphenylmethyl-L-glutamate), PBPLG, (poly{L-imino-1-[2-(4-biphenylylmethoxycarbonyl)ethyl]-2-oxoethylene}), (1d) is described. The viscosity behavior of this polymer in benzene/dichloroacetic acid mixtures (c=0,2.10 -3 - 1,4.10 -3 g/cm3) at 25°CC is investigated. The results are compared with measurements on poly(γ-benzyl-L-glutamate), PBLG, (poly[L-imino-1-(2-benzyloxycarbonylethyl)-2-oxoethylene]), (1c) under the same conditions. A transition from a rigid hydrogen bonded helix to a random solvated coil occurs in two stages for both: PBPLG (first stage 0-55%, second stage 55-100% dichloroacetic acid) and PBLG (first stage 0-70%, second stage 70-100% dichloroacetic acid). Therefore, the introduction of a p-phenyl substituent in PBLG leads to a less stable helix in benzene/dichloroacetic acid mixtures. The stability and viscosity behavior of PBLG in benzene/dichloroacetic acid mixtures (c=0,2.10 - 3 - 1,4.10 - 3g/cm3) is quite similar to the behavior of PBLG in m-cresol/dichloroacetic acid mixtures (c=1,0.10 - 3 - 4,0.10 - 3 g/cm3).
Original languageEnglish
Pages (from-to)3193-3206
JournalMakromolekulare Chemie
Volume175
Issue number11
DOIs
Publication statusPublished - 1974

Fingerprint

Dichloroacetic Acid
Dichloroacetic acid
glutamates
Benzene
Glutamic Acid
benzene
Viscosity
viscosity
acids
synthesis
helices
cresols
poly-gamma-benzyl-L-glutamate
Hydrogen
Polymers
coils
polymers
hydrogen

Keywords

  • IR-70771

Cite this

Feijen, Jan ; Sederel, Wim L. ; de Groot, Klaas ; de Visser, Anthonie C. ; Bantjes, Adriaan. / Synthesis and viscosity behavior of poly(γ-p-biphenylmethyl-L-glutamate) in benzene/dichloroacetic acid mixtures, a comparison with poly(γ-benzyl-L-glutamate). In: Makromolekulare Chemie. 1974 ; Vol. 175, No. 11. pp. 3193-3206.
@article{758e1d520a194ba988ff8e2b8416a594,
title = "Synthesis and viscosity behavior of poly(γ-p-biphenylmethyl-L-glutamate) in benzene/dichloroacetic acid mixtures, a comparison with poly(γ-benzyl-L-glutamate)",
abstract = "The synthesis of poly(γ-p-biphenylmethyl-L-glutamate), PBPLG, (poly{L-imino-1-[2-(4-biphenylylmethoxycarbonyl)ethyl]-2-oxoethylene}), (1d) is described. The viscosity behavior of this polymer in benzene/dichloroacetic acid mixtures (c=0,2.10 -3 - 1,4.10 -3 g/cm3) at 25°CC is investigated. The results are compared with measurements on poly(γ-benzyl-L-glutamate), PBLG, (poly[L-imino-1-(2-benzyloxycarbonylethyl)-2-oxoethylene]), (1c) under the same conditions. A transition from a rigid hydrogen bonded helix to a random solvated coil occurs in two stages for both: PBPLG (first stage 0-55{\%}, second stage 55-100{\%} dichloroacetic acid) and PBLG (first stage 0-70{\%}, second stage 70-100{\%} dichloroacetic acid). Therefore, the introduction of a p-phenyl substituent in PBLG leads to a less stable helix in benzene/dichloroacetic acid mixtures. The stability and viscosity behavior of PBLG in benzene/dichloroacetic acid mixtures (c=0,2.10 - 3 - 1,4.10 - 3g/cm3) is quite similar to the behavior of PBLG in m-cresol/dichloroacetic acid mixtures (c=1,0.10 - 3 - 4,0.10 - 3 g/cm3).",
keywords = "IR-70771",
author = "Jan Feijen and Sederel, {Wim L.} and {de Groot}, Klaas and {de Visser}, {Anthonie C.} and Adriaan Bantjes",
year = "1974",
doi = "10.1002/macp.1974.021751113",
language = "English",
volume = "175",
pages = "3193--3206",
journal = "Macromolecular chemistry and physics",
issn = "1022-1352",
publisher = "Wiley-VCH Verlag",
number = "11",

}

Synthesis and viscosity behavior of poly(γ-p-biphenylmethyl-L-glutamate) in benzene/dichloroacetic acid mixtures, a comparison with poly(γ-benzyl-L-glutamate). / Feijen, Jan; Sederel, Wim L.; de Groot, Klaas; de Visser, Anthonie C.; Bantjes, Adriaan.

In: Makromolekulare Chemie, Vol. 175, No. 11, 1974, p. 3193-3206.

Research output: Contribution to journalArticleAcademic

TY - JOUR

T1 - Synthesis and viscosity behavior of poly(γ-p-biphenylmethyl-L-glutamate) in benzene/dichloroacetic acid mixtures, a comparison with poly(γ-benzyl-L-glutamate)

AU - Feijen, Jan

AU - Sederel, Wim L.

AU - de Groot, Klaas

AU - de Visser, Anthonie C.

AU - Bantjes, Adriaan

PY - 1974

Y1 - 1974

N2 - The synthesis of poly(γ-p-biphenylmethyl-L-glutamate), PBPLG, (poly{L-imino-1-[2-(4-biphenylylmethoxycarbonyl)ethyl]-2-oxoethylene}), (1d) is described. The viscosity behavior of this polymer in benzene/dichloroacetic acid mixtures (c=0,2.10 -3 - 1,4.10 -3 g/cm3) at 25°CC is investigated. The results are compared with measurements on poly(γ-benzyl-L-glutamate), PBLG, (poly[L-imino-1-(2-benzyloxycarbonylethyl)-2-oxoethylene]), (1c) under the same conditions. A transition from a rigid hydrogen bonded helix to a random solvated coil occurs in two stages for both: PBPLG (first stage 0-55%, second stage 55-100% dichloroacetic acid) and PBLG (first stage 0-70%, second stage 70-100% dichloroacetic acid). Therefore, the introduction of a p-phenyl substituent in PBLG leads to a less stable helix in benzene/dichloroacetic acid mixtures. The stability and viscosity behavior of PBLG in benzene/dichloroacetic acid mixtures (c=0,2.10 - 3 - 1,4.10 - 3g/cm3) is quite similar to the behavior of PBLG in m-cresol/dichloroacetic acid mixtures (c=1,0.10 - 3 - 4,0.10 - 3 g/cm3).

AB - The synthesis of poly(γ-p-biphenylmethyl-L-glutamate), PBPLG, (poly{L-imino-1-[2-(4-biphenylylmethoxycarbonyl)ethyl]-2-oxoethylene}), (1d) is described. The viscosity behavior of this polymer in benzene/dichloroacetic acid mixtures (c=0,2.10 -3 - 1,4.10 -3 g/cm3) at 25°CC is investigated. The results are compared with measurements on poly(γ-benzyl-L-glutamate), PBLG, (poly[L-imino-1-(2-benzyloxycarbonylethyl)-2-oxoethylene]), (1c) under the same conditions. A transition from a rigid hydrogen bonded helix to a random solvated coil occurs in two stages for both: PBPLG (first stage 0-55%, second stage 55-100% dichloroacetic acid) and PBLG (first stage 0-70%, second stage 70-100% dichloroacetic acid). Therefore, the introduction of a p-phenyl substituent in PBLG leads to a less stable helix in benzene/dichloroacetic acid mixtures. The stability and viscosity behavior of PBLG in benzene/dichloroacetic acid mixtures (c=0,2.10 - 3 - 1,4.10 - 3g/cm3) is quite similar to the behavior of PBLG in m-cresol/dichloroacetic acid mixtures (c=1,0.10 - 3 - 4,0.10 - 3 g/cm3).

KW - IR-70771

U2 - 10.1002/macp.1974.021751113

DO - 10.1002/macp.1974.021751113

M3 - Article

VL - 175

SP - 3193

EP - 3206

JO - Macromolecular chemistry and physics

JF - Macromolecular chemistry and physics

SN - 1022-1352

IS - 11

ER -