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

Helinä Pohjanlehto, Harri Setälä (Corresponding Author), Kari Kammiovirta, Ali Harlin

Research output: Contribution to journalArticleScientificpeer-review

34 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)2736-2745
Number of pages10
JournalCarbohydrate Research
Volume346
Issue number17
DOIs
Publication statusPublished - 2011
MoE publication typeA1 Journal article-refereed

Fingerprint

Xylans
Hydrogels
Derivatives
Substitution reactions
Water
Hydrogel
Betula
Deionized water
Water absorption
Pore structure
Polymerization
Electron Scanning Microscopy
Pulp
Free Radicals
Swelling
Polymers
Nuclear magnetic resonance
Scanning electron microscopy
Acids
Chemical analysis

Keywords

  • Hydrogel
  • N,N'-diallylaldardiamides
  • xylan
  • renewable resources

Cite this

@article{63c33b9118de4402bd0d284968f7b264,
title = "The use of N,N'-diallylaldardiamides as cross-linkers in xylan derivatives-based hydrogels",
abstract = "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.",
keywords = "Hydrogel, N,N'-diallylaldardiamides, xylan, renewable resources",
author = "Helin{\"a} Pohjanlehto and Harri Set{\"a}l{\"a} and Kari Kammiovirta and Ali Harlin",
note = "Project code: 73895 task 1.3 chemistry",
year = "2011",
doi = "10.1016/j.carres.2011.09.028",
language = "English",
volume = "346",
pages = "2736--2745",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier",
number = "17",

}

The use of N,N'-diallylaldardiamides as cross-linkers in xylan derivatives-based hydrogels. / Pohjanlehto, Helinä; Setälä, Harri (Corresponding Author); Kammiovirta, Kari; Harlin, Ali.

In: Carbohydrate Research, Vol. 346, No. 17, 2011, p. 2736-2745.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - The use of N,N'-diallylaldardiamides as cross-linkers in xylan derivatives-based hydrogels

AU - Pohjanlehto, Helinä

AU - Setälä, Harri

AU - Kammiovirta, Kari

AU - Harlin, Ali

N1 - Project code: 73895 task 1.3 chemistry

PY - 2011

Y1 - 2011

N2 - 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.

AB - 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.

KW - Hydrogel

KW - N,N'-diallylaldardiamides

KW - xylan

KW - renewable resources

U2 - 10.1016/j.carres.2011.09.028

DO - 10.1016/j.carres.2011.09.028

M3 - Article

VL - 346

SP - 2736

EP - 2745

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 17

ER -