Synthesis and characterization of copolyanhydrides of carbohydrate-based galacteric acid and adipic acid

Tuomas Mehtiö (Corresponding Author), Leena Nurmi, Virpi Rämö, Hannu Mikkonen, Ali Harlin

Research output: Contribution to journalArticleScientificpeer-review

8 Citations (Scopus)

Abstract

A series of copolyanhydrides, consisting of 2,3,4,5-tetra-O-acetylgalactaric acid (AGA) and adipic acid (AA) as monomer units, was polymerized. Synthesis of AGA monomer consisted of two steps. First, O-acetylation of galactaric acid secondary hydroxyl groups was performed using acetic anhydride as a reagent. Acetic anhydride was then further used as a reagent in the synthesis of diacetyl mixed anhydride of AGA. Polymerizations were conducted as bulk condensation polymerization at 150°C. Thermal properties of the copolymers varied depending on monomer composition. Increase in the AGA content had a clear increasing effect on the Tg. A similar increasing effect was observed in Tm. The degree of crystallinity decreased as AGA content increased. There was a slightly lowering tendency in the molecular weights of the obtained polymers when the AGA content in the polymerization mixtures increased. The described synthesis route shows that bio-based aldaric acid monomers are potential candidates for the adjustment of thermal properties of polyanhydrides.
Original languageEnglish
Pages (from-to)102-110
JournalCarbohydrate Research
Volume402
DOIs
Publication statusPublished - 2015
MoE publication typeA1 Journal article-refereed

Fingerprint

Carbohydrates
Acids
Monomers
Polymerization
Polyanhydrides
Thermodynamic properties
Hot Temperature
Diacetyl
Acetylation
Anhydrides
Polycondensation
Hydroxyl Radical
adipic acid
Polymers
Copolymers
Molecular weight
Molecular Weight
Chemical analysis
acetic anhydride

Keywords

  • biopolymers
  • biodegradable
  • polyanhydrides
  • polycondensation
  • synthesis
  • renewable resources
  • acetylation

Cite this

Mehtiö, Tuomas ; Nurmi, Leena ; Rämö, Virpi ; Mikkonen, Hannu ; Harlin, Ali. / Synthesis and characterization of copolyanhydrides of carbohydrate-based galacteric acid and adipic acid. In: Carbohydrate Research. 2015 ; Vol. 402. pp. 102-110.
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title = "Synthesis and characterization of copolyanhydrides of carbohydrate-based galacteric acid and adipic acid",
abstract = "A series of copolyanhydrides, consisting of 2,3,4,5-tetra-O-acetylgalactaric acid (AGA) and adipic acid (AA) as monomer units, was polymerized. Synthesis of AGA monomer consisted of two steps. First, O-acetylation of galactaric acid secondary hydroxyl groups was performed using acetic anhydride as a reagent. Acetic anhydride was then further used as a reagent in the synthesis of diacetyl mixed anhydride of AGA. Polymerizations were conducted as bulk condensation polymerization at 150°C. Thermal properties of the copolymers varied depending on monomer composition. Increase in the AGA content had a clear increasing effect on the Tg. A similar increasing effect was observed in Tm. The degree of crystallinity decreased as AGA content increased. There was a slightly lowering tendency in the molecular weights of the obtained polymers when the AGA content in the polymerization mixtures increased. The described synthesis route shows that bio-based aldaric acid monomers are potential candidates for the adjustment of thermal properties of polyanhydrides.",
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author = "Tuomas Mehti{\"o} and Leena Nurmi and Virpi R{\"a}m{\"o} and Hannu Mikkonen and Ali Harlin",
year = "2015",
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Synthesis and characterization of copolyanhydrides of carbohydrate-based galacteric acid and adipic acid. / Mehtiö, Tuomas (Corresponding Author); Nurmi, Leena; Rämö, Virpi; Mikkonen, Hannu; Harlin, Ali.

In: Carbohydrate Research, Vol. 402, 2015, p. 102-110.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Synthesis and characterization of copolyanhydrides of carbohydrate-based galacteric acid and adipic acid

AU - Mehtiö, Tuomas

AU - Nurmi, Leena

AU - Rämö, Virpi

AU - Mikkonen, Hannu

AU - Harlin, Ali

PY - 2015

Y1 - 2015

N2 - A series of copolyanhydrides, consisting of 2,3,4,5-tetra-O-acetylgalactaric acid (AGA) and adipic acid (AA) as monomer units, was polymerized. Synthesis of AGA monomer consisted of two steps. First, O-acetylation of galactaric acid secondary hydroxyl groups was performed using acetic anhydride as a reagent. Acetic anhydride was then further used as a reagent in the synthesis of diacetyl mixed anhydride of AGA. Polymerizations were conducted as bulk condensation polymerization at 150°C. Thermal properties of the copolymers varied depending on monomer composition. Increase in the AGA content had a clear increasing effect on the Tg. A similar increasing effect was observed in Tm. The degree of crystallinity decreased as AGA content increased. There was a slightly lowering tendency in the molecular weights of the obtained polymers when the AGA content in the polymerization mixtures increased. The described synthesis route shows that bio-based aldaric acid monomers are potential candidates for the adjustment of thermal properties of polyanhydrides.

AB - A series of copolyanhydrides, consisting of 2,3,4,5-tetra-O-acetylgalactaric acid (AGA) and adipic acid (AA) as monomer units, was polymerized. Synthesis of AGA monomer consisted of two steps. First, O-acetylation of galactaric acid secondary hydroxyl groups was performed using acetic anhydride as a reagent. Acetic anhydride was then further used as a reagent in the synthesis of diacetyl mixed anhydride of AGA. Polymerizations were conducted as bulk condensation polymerization at 150°C. Thermal properties of the copolymers varied depending on monomer composition. Increase in the AGA content had a clear increasing effect on the Tg. A similar increasing effect was observed in Tm. The degree of crystallinity decreased as AGA content increased. There was a slightly lowering tendency in the molecular weights of the obtained polymers when the AGA content in the polymerization mixtures increased. The described synthesis route shows that bio-based aldaric acid monomers are potential candidates for the adjustment of thermal properties of polyanhydrides.

KW - biopolymers

KW - biodegradable

KW - polyanhydrides

KW - polycondensation

KW - synthesis

KW - renewable resources

KW - acetylation

U2 - 10.1016/j.carres.2014.07.009

DO - 10.1016/j.carres.2014.07.009

M3 - Article

VL - 402

SP - 102

EP - 110

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

ER -