Development of New D,L-Methionine-based Gelators

• Suga Shunichi

  Faculty of Textile Science & Technology, Shinshu University

• Suzuki Masahiro

  Interdisciplinary Graduate School of Science & Technology, Shinshu University

• Hanabusa Kenji

  Interdisciplinary Graduate School of Science & Technology, Shinshu University Division of Frontier Fibers, Institute for Fiber Engineering, ICCER, Shinshu University

Abstract

D,L-Methionine was chosen as a starting material for the preparation of a new gelator N-10-undecenoyl-D,L-methionylaminooctadecane (DL-Met-R₁₈). Three oligo (dimethylsiloxane)-containing gelators, DL-Met-R₁₈/Si₃, DL-Met-R₁₈/Si_7-8, and DL-Met-R₁₈/Si_14-15, were also prepared from DL-Met-R₁₈ by hydrosilylation reactions. Their gelation abilities were evaluated on the basis of the minimum gel concentration using nine solvents. Compound DL-Met-R₁₈ was able to gelate liquid paraffin and silicone oil, but it crystallized in most solvents. However, DL-Met-R₁₈/Si_7-8 resulted to be the best gelator, gelling eight solvents at low concentrations. The results of gelation tests demonstrated that the ability to form stable gels decreases in the following order: DL-Met-R₁₈/Si_7-8 ≈ DL-Met-R₁₈/Si_14-15 > DL-Met-R₁₈/Si₃ >> DL-Met-R₁₈. The aspects and thermal stabilities of the gels were investigated using three-component mixtures of solvents composed of hexadecyl 2-ethylhexanoate, liquid paraffin, and decamethylcyclopentasiloxane (66 combinations). DL-Met-R₁₈/Si₃, DL-Met-R₁₈/Si_7-8, and DL-Met-R₁₈/Si_14-15 could form gels with all these mixed solvent combinations; particularly, DL-Met-R₁₈/Si_7-8 gave rise to transparent or translucent gels. FT-IR spectra suggested that the formation of hydrogen bonds between the NH and C=O groups of the amides is one of driving forces involved in the gelation process. Aggregates comprising three-dimensional networks were studied by transmission electron microscopy. Moreover, the viscoelastic behavior of the gels was investigated by rheology measurements.

Journal

• Journal of Oleo Science

  Journal of Oleo Science 67 (5), 539-549, 2018

  Japan Oil Chemists' Society

Keywords

• gel
• gelator
• gelation
• methionine
• hydrogen bonding
• cosmetic
• siloxane

Details

• CRID: 1390001204091898112
• NII Article ID: 130006729578
• NII Book ID: AA11503337
• DOI: 10.5650/jos.ess17248
• ISSN: 13473352
• ISSN: 13458957
• HANDLE: 10091/00021969
• NDL BIB ID: 028953766
• PubMed: 29710040
• Web Site: https://soar-ir.repo.nii.ac.jp/records/21212
• Web Site: http://id.ndl.go.jp/bib/028953766
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I028953766
• Web Site: https://www.jstage.jst.go.jp/article/jos/67/5/67_ess17248/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • IRDB
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed