Preparation of poly(2-oxy-6-naphthoyl) and copolymers using reaction-induced phase separation during direct polymerization in the presence of boronic anhydride

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Abstract

Poly(2-oxy-6-naphthoyl) (PON) was obtained as precipitates by direct polymerization of 2-hydroxy-6-naphthoic acid (HNA) in the presence of boronic anhydrides such as 2,4,6-tris(3,4,5-trifluorophenyl)- 1,3,5,2,4,6- trioxatriborinane (TFBA) and 2,4,6-tri(biphenyl-4-yl)-1,3,5,2,4,6- trioxatriborinane (BPBA). The polymerizations were carried out in an aromatic solvent at 300°C for 24 h. Both morphology and molecular weight of the PON precipitates were considerably influenced by not only the structure of the boronic anhydride but also its concentration (cB). Spheres with needles on their surface were formed in the polymerization with TFBA at c B of 50-70 mol%, and those having smooth surface were obtained at cB of 100 mol%. The Mn increased with the value of c B in the range from 2.7 x 103 to 9.0 x 103. Aggregates of cone-like crystals were prepared in the polymerization with BPBA at cB of 10-30 mol%, and spheres having rugged surface were formed at cB of 50-100 mol%. The Mn also increased with the value of cB in the range from 5.4 x 103 to 12.9 x 10 3. These PON precipitates possessed high crystallinity in spite of the morphology. The copolymerization of HNA and 4- hydroxybenzoic acid (HBA) was also examined in the presence of BPBA at cB of 100 mol% with varying the content of HBA in feed (rf). Copolymers were obtained as spheres of which the content of 4- oxybenzoyl moiety was lower than the value of r f due to the difference in the solubility of the oligomers.

Original languageEnglish
Pages (from-to)1195-1202
Number of pages8
JournalPolymer Chemistry
Volume2
Issue number5
DOIs
Publication statusPublished - 2011

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Anhydrides
Polymerization
Phase separation
Copolymers
Precipitates
Acids
Hydroxybenzoates
Oligomers
Needles
Solubility
Copolymerization
Cones
Molecular Weight
Molecular weight
Crystals
1-naphthoic acid

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Biochemistry
  • Biomedical Engineering
  • Bioengineering

Cite this

@article{e8ccc653c7544df0bcc4b5df821b090c,
title = "Preparation of poly(2-oxy-6-naphthoyl) and copolymers using reaction-induced phase separation during direct polymerization in the presence of boronic anhydride",
abstract = "Poly(2-oxy-6-naphthoyl) (PON) was obtained as precipitates by direct polymerization of 2-hydroxy-6-naphthoic acid (HNA) in the presence of boronic anhydrides such as 2,4,6-tris(3,4,5-trifluorophenyl)- 1,3,5,2,4,6- trioxatriborinane (TFBA) and 2,4,6-tri(biphenyl-4-yl)-1,3,5,2,4,6- trioxatriborinane (BPBA). The polymerizations were carried out in an aromatic solvent at 300°C for 24 h. Both morphology and molecular weight of the PON precipitates were considerably influenced by not only the structure of the boronic anhydride but also its concentration (cB). Spheres with needles on their surface were formed in the polymerization with TFBA at c B of 50-70 mol{\%}, and those having smooth surface were obtained at cB of 100 mol{\%}. The Mn increased with the value of c B in the range from 2.7 x 103 to 9.0 x 103. Aggregates of cone-like crystals were prepared in the polymerization with BPBA at cB of 10-30 mol{\%}, and spheres having rugged surface were formed at cB of 50-100 mol{\%}. The Mn also increased with the value of cB in the range from 5.4 x 103 to 12.9 x 10 3. These PON precipitates possessed high crystallinity in spite of the morphology. The copolymerization of HNA and 4- hydroxybenzoic acid (HBA) was also examined in the presence of BPBA at cB of 100 mol{\%} with varying the content of HBA in feed (rf). Copolymers were obtained as spheres of which the content of 4- oxybenzoyl moiety was lower than the value of r f due to the difference in the solubility of the oligomers.",
author = "Masahiro Kihara and Shinichi Yamazaki and Kunio Kimura",
year = "2011",
doi = "10.1039/c0py00420k",
language = "English",
volume = "2",
pages = "1195--1202",
journal = "Polymer Chemistry",
issn = "1759-9954",
publisher = "Royal Society of Chemistry",
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TY - JOUR

T1 - Preparation of poly(2-oxy-6-naphthoyl) and copolymers using reaction-induced phase separation during direct polymerization in the presence of boronic anhydride

AU - Kihara, Masahiro

AU - Yamazaki, Shinichi

AU - Kimura, Kunio

PY - 2011

Y1 - 2011

N2 - Poly(2-oxy-6-naphthoyl) (PON) was obtained as precipitates by direct polymerization of 2-hydroxy-6-naphthoic acid (HNA) in the presence of boronic anhydrides such as 2,4,6-tris(3,4,5-trifluorophenyl)- 1,3,5,2,4,6- trioxatriborinane (TFBA) and 2,4,6-tri(biphenyl-4-yl)-1,3,5,2,4,6- trioxatriborinane (BPBA). The polymerizations were carried out in an aromatic solvent at 300°C for 24 h. Both morphology and molecular weight of the PON precipitates were considerably influenced by not only the structure of the boronic anhydride but also its concentration (cB). Spheres with needles on their surface were formed in the polymerization with TFBA at c B of 50-70 mol%, and those having smooth surface were obtained at cB of 100 mol%. The Mn increased with the value of c B in the range from 2.7 x 103 to 9.0 x 103. Aggregates of cone-like crystals were prepared in the polymerization with BPBA at cB of 10-30 mol%, and spheres having rugged surface were formed at cB of 50-100 mol%. The Mn also increased with the value of cB in the range from 5.4 x 103 to 12.9 x 10 3. These PON precipitates possessed high crystallinity in spite of the morphology. The copolymerization of HNA and 4- hydroxybenzoic acid (HBA) was also examined in the presence of BPBA at cB of 100 mol% with varying the content of HBA in feed (rf). Copolymers were obtained as spheres of which the content of 4- oxybenzoyl moiety was lower than the value of r f due to the difference in the solubility of the oligomers.

AB - Poly(2-oxy-6-naphthoyl) (PON) was obtained as precipitates by direct polymerization of 2-hydroxy-6-naphthoic acid (HNA) in the presence of boronic anhydrides such as 2,4,6-tris(3,4,5-trifluorophenyl)- 1,3,5,2,4,6- trioxatriborinane (TFBA) and 2,4,6-tri(biphenyl-4-yl)-1,3,5,2,4,6- trioxatriborinane (BPBA). The polymerizations were carried out in an aromatic solvent at 300°C for 24 h. Both morphology and molecular weight of the PON precipitates were considerably influenced by not only the structure of the boronic anhydride but also its concentration (cB). Spheres with needles on their surface were formed in the polymerization with TFBA at c B of 50-70 mol%, and those having smooth surface were obtained at cB of 100 mol%. The Mn increased with the value of c B in the range from 2.7 x 103 to 9.0 x 103. Aggregates of cone-like crystals were prepared in the polymerization with BPBA at cB of 10-30 mol%, and spheres having rugged surface were formed at cB of 50-100 mol%. The Mn also increased with the value of cB in the range from 5.4 x 103 to 12.9 x 10 3. These PON precipitates possessed high crystallinity in spite of the morphology. The copolymerization of HNA and 4- hydroxybenzoic acid (HBA) was also examined in the presence of BPBA at cB of 100 mol% with varying the content of HBA in feed (rf). Copolymers were obtained as spheres of which the content of 4- oxybenzoyl moiety was lower than the value of r f due to the difference in the solubility of the oligomers.

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U2 - 10.1039/c0py00420k

DO - 10.1039/c0py00420k

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