The use of N,N′-diallylaldardiamides as cross-linkers in xylan derivatives-based hydrogels

The preparation of a bio-based hydrogel by cross-linking derivatized xylan with sugar diacid based cross-linker. N,N′ -Diallylaldardiamides (DA) were synthesized from galactaric, xylaric, and arabinaric acids, and used as cross-linkers together with xylan (X) derivatives to create new bio-based hydr...

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Veröffentlicht in:Carbohydrate research 2011-12, Vol.346 (17), p.2736-2745
Hauptverfasser: Pohjanlehto, Helinä, Setälä, Harri, Kammiovirta, Kari, Harlin, Ali
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container_end_page 2745
container_issue 17
container_start_page 2736
container_title Carbohydrate research
container_volume 346
creator Pohjanlehto, Helinä
Setälä, Harri
Kammiovirta, Kari
Harlin, Ali
description The preparation of a bio-based hydrogel by cross-linking derivatized xylan with sugar diacid based cross-linker. N,N′ -Diallylaldardiamides (DA) were synthesized from galactaric, xylaric, and arabinaric acids, and used as cross-linkers together with xylan (X) derivatives to create new bio-based hydrogels. Birch pulp extracted xylan was derivatized to different degrees of substitution of 1-allyloxy-2-hydroxy-propyl (A) groups combined with 1-butyloxy-2-hydroxy-propyl (B) and/or hydroxypropyl (HP) groups. The hydrogels were prepared in water solution by UV induced free-radical cross-linking polymerization of derivatized xylan polymers without DA cross-linker (xylan derivative hydrogel) or in the presence of 1 or 5 wt % of DA cross-linker (DA hydrogel). Commercially available cross-linker (+)- N,N′-diallyltartardiamide (DAT) was also used. The degree of substitution (DS) of A, B, and HP groups in xylan derivatives was analyzed according to 1H NMR spectra. The DS values for the cross-linkable A groups of the derivatized xylans were 0.4 (HPX-A), 0.2 (HPX-BA), and 0.4 (X-BA). The hydrogels were examined with FT-IR and elemental analysis which proved the cross-linking successful. Water absorption of the hydrogels was examined in deionized water. Swelling degrees up to 350% were observed. The swollen morphology of the hydrogels was assessed by scanning electron microscopy (SEM). The presence of cross-linkers in DA hydrogels had only a small impact on the water absorbency when compared to xylan derivative hydrogels but a more uniform pore structure was achieved.
doi_str_mv 10.1016/j.carres.2011.09.028
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N,N′ -Diallylaldardiamides (DA) were synthesized from galactaric, xylaric, and arabinaric acids, and used as cross-linkers together with xylan (X) derivatives to create new bio-based hydrogels. Birch pulp extracted xylan was derivatized to different degrees of substitution of 1-allyloxy-2-hydroxy-propyl (A) groups combined with 1-butyloxy-2-hydroxy-propyl (B) and/or hydroxypropyl (HP) groups. The hydrogels were prepared in water solution by UV induced free-radical cross-linking polymerization of derivatized xylan polymers without DA cross-linker (xylan derivative hydrogel) or in the presence of 1 or 5 wt % of DA cross-linker (DA hydrogel). Commercially available cross-linker (+)- N,N′-diallyltartardiamide (DAT) was also used. The degree of substitution (DS) of A, B, and HP groups in xylan derivatives was analyzed according to 1H NMR spectra. The DS values for the cross-linkable A groups of the derivatized xylans were 0.4 (HPX-A), 0.2 (HPX-BA), and 0.4 (X-BA). The hydrogels were examined with FT-IR and elemental analysis which proved the cross-linking successful. Water absorption of the hydrogels was examined in deionized water. Swelling degrees up to 350% were observed. The swollen morphology of the hydrogels was assessed by scanning electron microscopy (SEM). 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N,N′ -Diallylaldardiamides (DA) were synthesized from galactaric, xylaric, and arabinaric acids, and used as cross-linkers together with xylan (X) derivatives to create new bio-based hydrogels. Birch pulp extracted xylan was derivatized to different degrees of substitution of 1-allyloxy-2-hydroxy-propyl (A) groups combined with 1-butyloxy-2-hydroxy-propyl (B) and/or hydroxypropyl (HP) groups. The hydrogels were prepared in water solution by UV induced free-radical cross-linking polymerization of derivatized xylan polymers without DA cross-linker (xylan derivative hydrogel) or in the presence of 1 or 5 wt % of DA cross-linker (DA hydrogel). Commercially available cross-linker (+)- N,N′-diallyltartardiamide (DAT) was also used. The degree of substitution (DS) of A, B, and HP groups in xylan derivatives was analyzed according to 1H NMR spectra. The DS values for the cross-linkable A groups of the derivatized xylans were 0.4 (HPX-A), 0.2 (HPX-BA), and 0.4 (X-BA). 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Setälä, Harri ; Kammiovirta, Kari ; Harlin, Ali</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c334t-c99ffacb869d688d2d6a21e94bcb9514815d3a9f660847c60454d19e94c27e773</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>absorption</topic><topic>acids</topic><topic>Allyl Compounds - chemical synthesis</topic><topic>Allyl Compounds - chemistry</topic><topic>Betula</topic><topic>Cross-Linking Reagents - chemical synthesis</topic><topic>Cross-Linking Reagents - chemistry</topic><topic>crosslinking</topic><topic>Fourier transform infrared spectroscopy</topic><topic>hydrocolloids</topic><topic>Hydrogel</topic><topic>Hydrogels - chemical synthesis</topic><topic>Hydrogels - chemistry</topic><topic>Hydrophobic and Hydrophilic Interactions</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Microscopy, Electron, Scanning</topic><topic>Molecular Structure</topic><topic>N,N′ -Diallylaldardiamides</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>polymerization</topic><topic>polymers</topic><topic>pulp</topic><topic>Renewable resources</topic><topic>scanning electron microscopy</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><topic>Sugar Acids - chemical synthesis</topic><topic>Sugar Acids - chemistry</topic><topic>Xylan</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pohjanlehto, Helinä</creatorcontrib><creatorcontrib>Setälä, Harri</creatorcontrib><creatorcontrib>Kammiovirta, Kari</creatorcontrib><creatorcontrib>Harlin, Ali</creatorcontrib><collection>AGRIS</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pohjanlehto, Helinä</au><au>Setälä, Harri</au><au>Kammiovirta, Kari</au><au>Harlin, Ali</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The use of N,N′-diallylaldardiamides as cross-linkers in xylan derivatives-based hydrogels</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2011-12-13</date><risdate>2011</risdate><volume>346</volume><issue>17</issue><spage>2736</spage><epage>2745</epage><pages>2736-2745</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>The preparation of a bio-based hydrogel by cross-linking derivatized xylan with sugar diacid based cross-linker. N,N′ -Diallylaldardiamides (DA) were synthesized from galactaric, xylaric, and arabinaric acids, and used as cross-linkers together with xylan (X) derivatives to create new bio-based hydrogels. Birch pulp extracted xylan was derivatized to different degrees of substitution of 1-allyloxy-2-hydroxy-propyl (A) groups combined with 1-butyloxy-2-hydroxy-propyl (B) and/or hydroxypropyl (HP) groups. The hydrogels were prepared in water solution by UV induced free-radical cross-linking polymerization of derivatized xylan polymers without DA cross-linker (xylan derivative hydrogel) or in the presence of 1 or 5 wt % of DA cross-linker (DA hydrogel). Commercially available cross-linker (+)- N,N′-diallyltartardiamide (DAT) was also used. The degree of substitution (DS) of A, B, and HP groups in xylan derivatives was analyzed according to 1H NMR spectra. The DS values for the cross-linkable A groups of the derivatized xylans were 0.4 (HPX-A), 0.2 (HPX-BA), and 0.4 (X-BA). The hydrogels were examined with FT-IR and elemental analysis which proved the cross-linking successful. Water absorption of the hydrogels was examined in deionized water. Swelling degrees up to 350% were observed. The swollen morphology of the hydrogels was assessed by scanning electron microscopy (SEM). The presence of cross-linkers in DA hydrogels had only a small impact on the water absorbency when compared to xylan derivative hydrogels but a more uniform pore structure was achieved.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>22047746</pmid><doi>10.1016/j.carres.2011.09.028</doi><tpages>10</tpages></addata></record>
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source MEDLINE; Access via ScienceDirect (Elsevier)
subjects absorption
acids
Allyl Compounds - chemical synthesis
Allyl Compounds - chemistry
Betula
Cross-Linking Reagents - chemical synthesis
Cross-Linking Reagents - chemistry
crosslinking
Fourier transform infrared spectroscopy
hydrocolloids
Hydrogel
Hydrogels - chemical synthesis
Hydrogels - chemistry
Hydrophobic and Hydrophilic Interactions
Magnetic Resonance Spectroscopy
Microscopy, Electron, Scanning
Molecular Structure
N,N′ -Diallylaldardiamides
nuclear magnetic resonance spectroscopy
polymerization
polymers
pulp
Renewable resources
scanning electron microscopy
Spectroscopy, Fourier Transform Infrared
Sugar Acids - chemical synthesis
Sugar Acids - chemistry
Xylan
title The use of N,N′-diallylaldardiamides as cross-linkers in xylan derivatives-based hydrogels
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