Loading…
Synthesis and characterization of polyhydrazides and poly(1,3,4-oxadiazole)s containing multiple arylene ether linkages and pendent pentadecyl chains
A new diacylhydrazide monomer, namely, 4-(4-(4-(4-(hydrazinocarbonyl)phenoxy)-2-pentadecylphenoxy)phenoxy) benzohydrazide (HPPDPB), was synthesized starting from 4-(4-hydroxyphenoxy)-3-pentadecylphenol. HPPDPB was polycondensed with terephthalic acid chloride (TPC), isophthalic acid chloride (IPC) a...
Saved in:
Published in: | High performance polymers 2017-09, Vol.29 (7), p.836-848 |
---|---|
Main Authors: | , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | cdi_FETCH-LOGICAL-c281t-fdfbe305893832e83d2713a614fe620933a861e7a577a663f45817f083758d683 |
---|---|
cites | cdi_FETCH-LOGICAL-c281t-fdfbe305893832e83d2713a614fe620933a861e7a577a663f45817f083758d683 |
container_end_page | 848 |
container_issue | 7 |
container_start_page | 836 |
container_title | High performance polymers |
container_volume | 29 |
creator | Tawade, Bhausaheb V Valsange, Nitin G Wadgaonkar, Prakash P |
description | A new diacylhydrazide monomer, namely, 4-(4-(4-(4-(hydrazinocarbonyl)phenoxy)-2-pentadecylphenoxy)phenoxy) benzohydrazide (HPPDPB), was synthesized starting from 4-(4-hydroxyphenoxy)-3-pentadecylphenol. HPPDPB was polycondensed with terephthalic acid chloride (TPC), isophthalic acid chloride (IPC) and a mixture of TPC and IPC (50:50 mol%) to obtain polyhydrazides containing multiple arylene ether linkages in the backbone and pendent pentadecyl chains. Polyhydrazides were subsequently cyclized in the presence of phosphorus oxychloride to obtain the corresponding poly(1,3,4-oxadiazole)s. Polyhydrazides and poly(1,3,4-oxadiazole)s exhibited inherent viscosities in the range 0.65–0.72 dL g−1 and 0.54–0.62 dL g−1, respectively, which indicated the formation of reasonably high-molecular weight polymers. Polyhydrazides were soluble in polar aprotic solvents such as N,N-dimethylformamide, N,N-dimethylacetamide (DMAc), 1-methyl-2-pyrrolidinone and pyridine whereas poly(1,3,4-oxadiazole)s exhibited excellent solubility even in common organic solvents such as chloroform, dichloromethane and tetrahydrofuran. Tough, transparent and flexible films of polyhydrazides and poly(1,3,4-oxadiazole)s could be cast from DMAc and chloroform solutions, respectively. X-Ray diffraction studies revealed amorphous nature of polyhydrazides and poly(1,3,4-oxadiazole)s and the formation of layered structure was observed due to ordered packing of pentadecyl chains. The 10% decomposition temperature (T
10) values for poly(1,3,4-oxadiazole)s were in the range 425–440°C indicating their good thermal stability. Glass transition temperature (T
g) values of polyhydrazides and poly(1,3,4-oxadiazole)s were in the range 175–192°C and 92–103°C, respectively. The excellent solubility characteristics and the large gap between T
g (92–103°C) and T
10 (425–440°C) values give poly(1,3,4-oxadiazole)-containing pendent pentadecyl chains better opportunities for processability. |
doi_str_mv | 10.1177/0954008316660368 |
format | article |
fullrecord | <record><control><sourceid>sage_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1177_0954008316660368</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sage_id>10.1177_0954008316660368</sage_id><sourcerecordid>10.1177_0954008316660368</sourcerecordid><originalsourceid>FETCH-LOGICAL-c281t-fdfbe305893832e83d2713a614fe620933a861e7a577a663f45817f083758d683</originalsourceid><addsrcrecordid>eNp1UEtLAzEQDqJgfdw95qjQ1cxmN5seRXxBwYN6XuJm0qbGpCQpuP0f_l93qV4ETwPzPeabj5AzYJcATXPFZnXFmOQghGBcyD0yAS6gEBWU-2QywsWIH5KjlFaMAUioJ-Trufd5ickmqrym3VJF1WWMdquyDZ4GQ9fB9cteR7W1Gne0cXUOUz6tivCptFXb4PAi0S74rKy3fkE_Ni7btUOqYu_QI8XhTKTO-ne1-LVBr9HncWalsevdGMD6dEIOjHIJT3_mMXm9u325eSjmT_ePN9fzoisl5MJo84ac1XLGJS9Rcl02wJWAyqAo2YxzJQVgo-qmUUJwU9USGjO00NRSC8mPCdv5djGkFNG062g_hsQtsHastf1b6yApdpI0vNGuwib6IeH__G8eBHnW</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Synthesis and characterization of polyhydrazides and poly(1,3,4-oxadiazole)s containing multiple arylene ether linkages and pendent pentadecyl chains</title><source>SAGE</source><creator>Tawade, Bhausaheb V ; Valsange, Nitin G ; Wadgaonkar, Prakash P</creator><creatorcontrib>Tawade, Bhausaheb V ; Valsange, Nitin G ; Wadgaonkar, Prakash P</creatorcontrib><description>A new diacylhydrazide monomer, namely, 4-(4-(4-(4-(hydrazinocarbonyl)phenoxy)-2-pentadecylphenoxy)phenoxy) benzohydrazide (HPPDPB), was synthesized starting from 4-(4-hydroxyphenoxy)-3-pentadecylphenol. HPPDPB was polycondensed with terephthalic acid chloride (TPC), isophthalic acid chloride (IPC) and a mixture of TPC and IPC (50:50 mol%) to obtain polyhydrazides containing multiple arylene ether linkages in the backbone and pendent pentadecyl chains. Polyhydrazides were subsequently cyclized in the presence of phosphorus oxychloride to obtain the corresponding poly(1,3,4-oxadiazole)s. Polyhydrazides and poly(1,3,4-oxadiazole)s exhibited inherent viscosities in the range 0.65–0.72 dL g−1 and 0.54–0.62 dL g−1, respectively, which indicated the formation of reasonably high-molecular weight polymers. Polyhydrazides were soluble in polar aprotic solvents such as N,N-dimethylformamide, N,N-dimethylacetamide (DMAc), 1-methyl-2-pyrrolidinone and pyridine whereas poly(1,3,4-oxadiazole)s exhibited excellent solubility even in common organic solvents such as chloroform, dichloromethane and tetrahydrofuran. Tough, transparent and flexible films of polyhydrazides and poly(1,3,4-oxadiazole)s could be cast from DMAc and chloroform solutions, respectively. X-Ray diffraction studies revealed amorphous nature of polyhydrazides and poly(1,3,4-oxadiazole)s and the formation of layered structure was observed due to ordered packing of pentadecyl chains. The 10% decomposition temperature (T
10) values for poly(1,3,4-oxadiazole)s were in the range 425–440°C indicating their good thermal stability. Glass transition temperature (T
g) values of polyhydrazides and poly(1,3,4-oxadiazole)s were in the range 175–192°C and 92–103°C, respectively. The excellent solubility characteristics and the large gap between T
g (92–103°C) and T
10 (425–440°C) values give poly(1,3,4-oxadiazole)-containing pendent pentadecyl chains better opportunities for processability.</description><identifier>ISSN: 0954-0083</identifier><identifier>EISSN: 1361-6412</identifier><identifier>DOI: 10.1177/0954008316660368</identifier><language>eng</language><publisher>London, England: SAGE Publications</publisher><ispartof>High performance polymers, 2017-09, Vol.29 (7), p.836-848</ispartof><rights>The Author(s) 2016</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-fdfbe305893832e83d2713a614fe620933a861e7a577a663f45817f083758d683</citedby><cites>FETCH-LOGICAL-c281t-fdfbe305893832e83d2713a614fe620933a861e7a577a663f45817f083758d683</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925,79364</link.rule.ids></links><search><creatorcontrib>Tawade, Bhausaheb V</creatorcontrib><creatorcontrib>Valsange, Nitin G</creatorcontrib><creatorcontrib>Wadgaonkar, Prakash P</creatorcontrib><title>Synthesis and characterization of polyhydrazides and poly(1,3,4-oxadiazole)s containing multiple arylene ether linkages and pendent pentadecyl chains</title><title>High performance polymers</title><description>A new diacylhydrazide monomer, namely, 4-(4-(4-(4-(hydrazinocarbonyl)phenoxy)-2-pentadecylphenoxy)phenoxy) benzohydrazide (HPPDPB), was synthesized starting from 4-(4-hydroxyphenoxy)-3-pentadecylphenol. HPPDPB was polycondensed with terephthalic acid chloride (TPC), isophthalic acid chloride (IPC) and a mixture of TPC and IPC (50:50 mol%) to obtain polyhydrazides containing multiple arylene ether linkages in the backbone and pendent pentadecyl chains. Polyhydrazides were subsequently cyclized in the presence of phosphorus oxychloride to obtain the corresponding poly(1,3,4-oxadiazole)s. Polyhydrazides and poly(1,3,4-oxadiazole)s exhibited inherent viscosities in the range 0.65–0.72 dL g−1 and 0.54–0.62 dL g−1, respectively, which indicated the formation of reasonably high-molecular weight polymers. Polyhydrazides were soluble in polar aprotic solvents such as N,N-dimethylformamide, N,N-dimethylacetamide (DMAc), 1-methyl-2-pyrrolidinone and pyridine whereas poly(1,3,4-oxadiazole)s exhibited excellent solubility even in common organic solvents such as chloroform, dichloromethane and tetrahydrofuran. Tough, transparent and flexible films of polyhydrazides and poly(1,3,4-oxadiazole)s could be cast from DMAc and chloroform solutions, respectively. X-Ray diffraction studies revealed amorphous nature of polyhydrazides and poly(1,3,4-oxadiazole)s and the formation of layered structure was observed due to ordered packing of pentadecyl chains. The 10% decomposition temperature (T
10) values for poly(1,3,4-oxadiazole)s were in the range 425–440°C indicating their good thermal stability. Glass transition temperature (T
g) values of polyhydrazides and poly(1,3,4-oxadiazole)s were in the range 175–192°C and 92–103°C, respectively. The excellent solubility characteristics and the large gap between T
g (92–103°C) and T
10 (425–440°C) values give poly(1,3,4-oxadiazole)-containing pendent pentadecyl chains better opportunities for processability.</description><issn>0954-0083</issn><issn>1361-6412</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp1UEtLAzEQDqJgfdw95qjQ1cxmN5seRXxBwYN6XuJm0qbGpCQpuP0f_l93qV4ETwPzPeabj5AzYJcATXPFZnXFmOQghGBcyD0yAS6gEBWU-2QywsWIH5KjlFaMAUioJ-Trufd5ickmqrym3VJF1WWMdquyDZ4GQ9fB9cteR7W1Gne0cXUOUz6tivCptFXb4PAi0S74rKy3fkE_Ni7btUOqYu_QI8XhTKTO-ne1-LVBr9HncWalsevdGMD6dEIOjHIJT3_mMXm9u325eSjmT_ePN9fzoisl5MJo84ac1XLGJS9Rcl02wJWAyqAo2YxzJQVgo-qmUUJwU9USGjO00NRSC8mPCdv5djGkFNG062g_hsQtsHastf1b6yApdpI0vNGuwib6IeH__G8eBHnW</recordid><startdate>201709</startdate><enddate>201709</enddate><creator>Tawade, Bhausaheb V</creator><creator>Valsange, Nitin G</creator><creator>Wadgaonkar, Prakash P</creator><general>SAGE Publications</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201709</creationdate><title>Synthesis and characterization of polyhydrazides and poly(1,3,4-oxadiazole)s containing multiple arylene ether linkages and pendent pentadecyl chains</title><author>Tawade, Bhausaheb V ; Valsange, Nitin G ; Wadgaonkar, Prakash P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-fdfbe305893832e83d2713a614fe620933a861e7a577a663f45817f083758d683</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tawade, Bhausaheb V</creatorcontrib><creatorcontrib>Valsange, Nitin G</creatorcontrib><creatorcontrib>Wadgaonkar, Prakash P</creatorcontrib><collection>CrossRef</collection><jtitle>High performance polymers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tawade, Bhausaheb V</au><au>Valsange, Nitin G</au><au>Wadgaonkar, Prakash P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and characterization of polyhydrazides and poly(1,3,4-oxadiazole)s containing multiple arylene ether linkages and pendent pentadecyl chains</atitle><jtitle>High performance polymers</jtitle><date>2017-09</date><risdate>2017</risdate><volume>29</volume><issue>7</issue><spage>836</spage><epage>848</epage><pages>836-848</pages><issn>0954-0083</issn><eissn>1361-6412</eissn><abstract>A new diacylhydrazide monomer, namely, 4-(4-(4-(4-(hydrazinocarbonyl)phenoxy)-2-pentadecylphenoxy)phenoxy) benzohydrazide (HPPDPB), was synthesized starting from 4-(4-hydroxyphenoxy)-3-pentadecylphenol. HPPDPB was polycondensed with terephthalic acid chloride (TPC), isophthalic acid chloride (IPC) and a mixture of TPC and IPC (50:50 mol%) to obtain polyhydrazides containing multiple arylene ether linkages in the backbone and pendent pentadecyl chains. Polyhydrazides were subsequently cyclized in the presence of phosphorus oxychloride to obtain the corresponding poly(1,3,4-oxadiazole)s. Polyhydrazides and poly(1,3,4-oxadiazole)s exhibited inherent viscosities in the range 0.65–0.72 dL g−1 and 0.54–0.62 dL g−1, respectively, which indicated the formation of reasonably high-molecular weight polymers. Polyhydrazides were soluble in polar aprotic solvents such as N,N-dimethylformamide, N,N-dimethylacetamide (DMAc), 1-methyl-2-pyrrolidinone and pyridine whereas poly(1,3,4-oxadiazole)s exhibited excellent solubility even in common organic solvents such as chloroform, dichloromethane and tetrahydrofuran. Tough, transparent and flexible films of polyhydrazides and poly(1,3,4-oxadiazole)s could be cast from DMAc and chloroform solutions, respectively. X-Ray diffraction studies revealed amorphous nature of polyhydrazides and poly(1,3,4-oxadiazole)s and the formation of layered structure was observed due to ordered packing of pentadecyl chains. The 10% decomposition temperature (T
10) values for poly(1,3,4-oxadiazole)s were in the range 425–440°C indicating their good thermal stability. Glass transition temperature (T
g) values of polyhydrazides and poly(1,3,4-oxadiazole)s were in the range 175–192°C and 92–103°C, respectively. The excellent solubility characteristics and the large gap between T
g (92–103°C) and T
10 (425–440°C) values give poly(1,3,4-oxadiazole)-containing pendent pentadecyl chains better opportunities for processability.</abstract><cop>London, England</cop><pub>SAGE Publications</pub><doi>10.1177/0954008316660368</doi><tpages>13</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0954-0083 |
ispartof | High performance polymers, 2017-09, Vol.29 (7), p.836-848 |
issn | 0954-0083 1361-6412 |
language | eng |
recordid | cdi_crossref_primary_10_1177_0954008316660368 |
source | SAGE |
title | Synthesis and characterization of polyhydrazides and poly(1,3,4-oxadiazole)s containing multiple arylene ether linkages and pendent pentadecyl chains |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T23%3A23%3A43IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-sage_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20and%20characterization%20of%20polyhydrazides%20and%20poly(1,3,4-oxadiazole)s%20containing%20multiple%20arylene%20ether%20linkages%20and%20pendent%20pentadecyl%20chains&rft.jtitle=High%20performance%20polymers&rft.au=Tawade,%20Bhausaheb%20V&rft.date=2017-09&rft.volume=29&rft.issue=7&rft.spage=836&rft.epage=848&rft.pages=836-848&rft.issn=0954-0083&rft.eissn=1361-6412&rft_id=info:doi/10.1177/0954008316660368&rft_dat=%3Csage_cross%3E10.1177_0954008316660368%3C/sage_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c281t-fdfbe305893832e83d2713a614fe620933a861e7a577a663f45817f083758d683%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rft_sage_id=10.1177_0954008316660368&rfr_iscdi=true |