Synthesis and Properties of 1,2,3,4-Butanetetracarboxylic Acid Type Gemini Surfactants with Semifluoroalkyl Chain as Hydrophobic Group

Tokuzo Kawase; Yoshifumi Nomura; Tatsuo Oida

doi:10.3139/113.110390

Published by De Gruyter September 15, 2015

Synthesis and Properties of 1,2,3,4-Butanetetracarboxylic Acid Type Gemini Surfactants with Semifluoroalkyl Chain as Hydrophobic Group

Synthese und Eigenschaften von 1,2,3,4-Butantetracarbonsäure-Geminitensiden mit Semifluoroalkylketten als hydrophoben Teil

Tokuzo Kawase , Yoshifumi Nomura and Tatsuo Oida

From the journal Tenside Surfactants Detergents

https://doi.org/10.3139/113.110390

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Abstract

Two kinds of 1,2,3,4-butanetetracarboxylic acid type gemini surfactants having semifluoroalkyl groups (Rf-(CH₂)_n-; Rf = C₈F₁₇, n = 2,3,4,5,6,8,11) as diester of 2,3-bis-COOH and 1,4-bis-COOH were prepared from 1,2,3,6-tetrahydrophthalic anhydride as the key material. Their surface properties were studied by surface tension and surface pressure-area (π–A) measurements. Semifluoroalkylated geminis showed excellent surface tension re-ducing ability, but the values of the critical micelle concentration (CMC) and γ_CMC remained nearly unaffected by the methylene chain length. From the zero-pressure molecular areas of semifluoro-alkylated geminis and the compression modulus analysis, it was clarified that semifluoroalkylated gemini surfactants having short methylene chains would form more rigid monolayers than those having long methylene chains. But, there were not very large differences in surface properties between two geminis having the same methylene chain length.

Kurzfassung

Mit dem Ausgangsmaterial 1,2,3,6-Tetrahy-drophthalsäureanhydrid wurden zwei Arten von 1,2,3,4-Butantetracarbonsäure-Geminitensiden präpariert. Diese Ten-side besitzen Semifluoroalkylgruppen (Rf-(CH₂)_n-; Rf = C₈F₁₇, n = 2,3,4,5,6,8,11) als Diester der 2,3-Bis-COOH und 1,4-Bis-COOH. Ihre oberflächenaktiven Eigenschaften wurden mittels Messungen der Oberflächenspannung und des Oberflächenfilmdrucks studiert. Die semifluoroalkylierten Geminitenside zeigten eine hervorragende Reduktion der Oberflächenspannung; die CMC-Werte und die Oberflächenspannung an der CMC wurden von der Methylenkettenlänge kaum beeinflusst. Mit dem aus den Filmdruckmessungen bestimmten Platzbedarf der semifluoroalkylierten Geminitenside und der Kompressionsmodulanalyse wird deutlich, dass semifluoroalkylierte Geminitenside mit -einer kurzen Methylenkette steifere Monolagen bilden als die Geminitenside mit einer langen Methylenkette. Aber die Unterschiede der oberflächenaktiven Eigenschaften zwischen zwei Geminitensiden mit gleichlangen Methylenketten sind nicht sehr groß.

Key words: Gemini surfactants; semifluoroalkyl; 1,2,3,4-butanetetracarboxylic acid; surface tension; surface pressure-area measurement

Stichwörter: Geminitenside; semifluoroalkylierte; 1,2,3,4-Butantetracarbonsäure; Oberflächenspannung; Oberflächenfilmdruckmessungen

*Correspondence address, Professor Tokuzo Kawase, Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Hashigamicho 1, Matsugasaki, Sakyoku, Kyoto 606 – 8585, Japan, Tel.: +81-75-7 24-75 15, Fax: +81-75-7 24-75 15, E-Mail: kawase@kit.ac.jp

Tokuzo Kawase was born in 1951. He is a Professor of chemistry at Kyoto Institute of Technology. He received his D. Engineering from Kyoto University in 1979 and another Ph. D. from Osaka City University in 1995. His current scientific interests are focused on the synthesis of novel surfactants including fluorinated surfactants.

Yoshifumi Nomura completed his M. Sc. in applied chemistry from Kyoto Institute of Technology. Presently he is working at Matsui Chemical Co., Ltd.

Tatsuo Oida is an Associate Professor at Kyoto Institute of Technology. His current scientific interests are focused on the synthesis of novel surfactants and their structure-related surfacant properties.

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Received: 2015-02-26

Accepted: 2015-06-22

Published Online: 2015-09-15

Published in Print: 2015-09-15

Synthesis and Properties of 1,2,3,4-Butanetetracarboxylic Acid Type Gemini Surfactants with Semifluoroalkyl Chain as Hydrophobic Group

Abstract

Kurzfassung

References

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