Synthesis and Properties of 1,2,3,4-Butanetetracarboxylic Acid Type Gemini Surfactants with Semifluoroalkyl Chain as Hydrophobic Group
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Tokuzo Kawase
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 γCMC 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.
References
1. Kissa, E.: Fluorinated Surfactants and Repellents, 2nd ed.Surfactant Science Series, Vol. 97, Marcel Dekker Inc.New York (2001).Suche in Google Scholar
2. Houde, M.; Martin, J. W.; Letcher, R. J.; Solomon, K. R. and Muir, D. C.: Biological monitoring of polyfluoroalkyl substances: A review, Environ. Sci. Technol.40 (2006) 3463–3473. 10.1021/es052580bSuche in Google Scholar
3. Calafat, A. M.; Wong, L. Y.; Kuklenyik, Z.; Reidy, J. A. and Needham, L. L.: Polyfluoroalkyl chemicals in the U.S. population: data from the National Health and Nutrition Examination Survey (NHANES) 2003–2004 and comparisons with NHANES 1999–2000, Environ Health Perspect. 115 (2007) 1596–1602. 10.1289/ehp.10598Suche in Google Scholar
4. Menger, F. M. and Littau, C. A.: Gemini-surfactants: synthesis properties, J. Am. Chem. Soc.113 (1991) 1451–1452. 10.1021/ja00004a077Suche in Google Scholar
5. Menger, F. M. and Littau, C. A.: Gemini surfactants: a new class of self-assembling molecules, J. Am. Chem. Soc.115 (1993) 10083–10090. 10.1021/ja00075a025Suche in Google Scholar
6. Menger, F. M. and Keiper, J. S.: Gemini surfactants, Angew. Chem. Int. Ed.39 (2000) 1906–1920. 10.1002/1521-3773(20000602)39:11%3C1906::AID-ANIE1906%3E3.0.CO;2-QSuche in Google Scholar
7. Zana, R.: Dimeric and oligomeric surfactants. Behavior at interfaces and in aqueous solution: a review, Adv. Colloid. Interface Sci.97 (2002), 203–251. 10.1016/S0001-8686(01)00069-0Suche in Google Scholar
8. Zana, R.: Dimeric (Gemini) surfactants: effect of the spacer group on the association behavior in aqueous solution, J. Colloid. Interface Sci.248 (2002) 203–220. 10.1006/jcis.2001.8104Suche in Google Scholar
9. Kawase, T., Iidzuka, J. and Oida, T.: A novel synthesis of SO3H type gemini surfactant having semifluoroalkyl group as hydrophobic group, J. Oleo Sci.59 (2010) 483–493. 10.5650/jos.59.483Suche in Google Scholar
10. Kawase, T., Ankyu, T. and Oida, T.: Synthesis and Surface Properties of CO2H Type Gemini Surfactant Having Semifluoroalkyl Group as Hydrophobic Group, Tenside Surfactants Detergents49 (2012) 498–507. 10.3139/113.110223Suche in Google Scholar
11. Kawase, T., Okada, K. and Oida, T.: Novel Fluorinated Gemini Surfactants with γ-Butyrolactone Segments, J. Oleo Sci.64 (2015) 169–182. 10.5650/jos.ess14193Suche in Google Scholar
12. Brace, N. O.: Long Chain Alkanoic and Alkenoic Acids with Perfluorolakyl Terminal Segments. J. Org. Chem.27 (1962) 4491–4498. 10.1021/jo01059a090Suche in Google Scholar
13. Chen, Y. L., Sano, M., Kawaguchi, M., Yu, H. and Zografi, G.: Static and dynamic properties of pentadecanoic acid monolayers at the air-water interface, Langmuir2 (1986) 349–354. 10.1021/la00069a018Suche in Google Scholar
14. Kajiyama, T., Morimoto, N., Uchida, M. and Oishi, Y.: Static Viscoelastic Characteristics-Aggregation Structure Relationships of Monolayers at Air–Water Interface, Chem. Lett.18 (1989) 1047–1050. 10.1246/cl.1989.1047Suche in Google Scholar
15. Aratani, K.: Multibranched dipolar compounds for surfactants, their manufacture and uses as emulsifiers, dispersants and detergents, Jpn. Kokai Tokkyo Koho (2000), JP 2000219654.Suche in Google Scholar
16. Kojima, M., Nakamura, Y., Ishikawa, T. and Takeuchi, S.: Fluorous dimethylthiocabamate (FDMTC) protecting groups for alcohols, Tetrahedron Lett.47 (2006) 6309–6314. 10.1016/j.tetlet.2006.05.142Suche in Google Scholar
17. De Campo, F., Lastécouères, D., Vincent, J.-M. and Verlhac, J.-B.: Copper(I) Complexes Mediated Cyclization Reaction of Unsaturated Ester under Fluoro Biphasic Procedure, J. Org. Chem.64 (1999) 4969–4971. 10.1021/jo990134zSuche in Google Scholar PubMed
18. Somekawa, K., Noura, M., Aoki, S., Noma, S. and Shimo, T.: Synthesis of Tetrasubstituted Cyclopentanes, Organic Preparations and Procedures International25 (1993) 449–456. 10.1080/00304949309457988Suche in Google Scholar
19. Paris, G., Berlinguet, L., Gaudry, R., English, J., Dayan, J. E.: Glutaric Acid and Glutarimide, Organic Syntheses47 (2003). 10.1002/0471264180.os037.16Suche in Google Scholar
20. Gupta, D. N., Hodge, P. and Davies, J. E.: Oxidation reactions using sodium metaperiodate supported on silica gel, J. Chem. Soc. Perkin Trans.1 (1981) 2970–2973. 10.1039/P19810002970Suche in Google Scholar
21. Oida, T., Okumura, A., Takeuchi, D., Chau, H. N. and Kawase, T.: New Oxidation Methods of Carbon-Carbon Double Bond to Dicarboxylic Acid using Nitric Acid and Ozone, Material Technology31 (2013) 17–26.Suche in Google Scholar
22. Fujitani, K., Mizutani, T., Oida, T. and Kawase, T.: Oxidative cleavage with hydrogen peroxide: preparation of polycarboxylic acids from cyclic olefins, J. Oleo Sci.58 (2009) 37–42. 10.5650/jos.58.37Suche in Google Scholar PubMed
23. Rosen, M. J. and Kunjappu, J. T.: Surfactants and Interfacial Phenomena, 4th Edition, John Wiley and SonsNew York (2012). 10.1002/9781118228920Suche in Google Scholar
24. Aisaka, T., Oida, T. and Kawase, T.: A novel synthesis of succinic acid type Gemini surfactant by the functional group interconversion of Corynomicolic acid, J. Oleo Sci.56 (2007) 633–644. 10.5650/jos.56.633Suche in Google Scholar PubMed
25. Kawase, T., Saito, I. and Oida, T.: Effects of Hydrophobic Chain length on Temperature Dependency of Monolayer Behavior of Ester Type Tartaric Gemini, J. Oleo Sci.60 (2011) 61–69. 10.5650/jos.60.61Suche in Google Scholar PubMed
26. Kawase, T., Ohshita, S., Yoshimasu, C. and Oida, T.: A novel design of water- and oil-repellent surface modifier having double-fluoroalkyl groups, in: Mittal, K. L. (Ed.), Contact Angle, Wettability and Adhesion, Vol. 6, Koninklijke Brill (2009) 173–189. 10.1163/ej.9789004169326.i-400.77Suche in Google Scholar
27. Yoshimura, T.; Ohno, A.; Esumi, K.: Equilibrium and dynamic surface tension properties of partially fluorinated quaternary ammonium salt gemini surfactants. Langmuir22 (2006) 4643–4648. 10.1021/la0534266Suche in Google Scholar PubMed
28. Matsuoka, K.; Yoshimura, T.; Shikimoto, T.; Hamada, J.; Yamawaki, M.; Honda, C.; Endo, K.: Molecular aggregates of partially fluorinated quaternary ammonium salt gemini surfactants. Langmuir23 (2007) 10990–10994. 10.1021/la701525cSuche in Google Scholar PubMed
29. El, K. M.; Taffin, G. E.; Baklouti, A.; Guittard, F.: Synthesis and surface properties of semi-fluorinated gemini surfactants with two reactive bromo pendant groups. J. Colloid Interface Sci.357 (2011) 129–134. 10.1016/j.jcis.2011.02.003Suche in Google Scholar PubMed
© 2015, Carl Hanser Publisher, Munich
Artikel in diesem Heft
- Contents/Inhalt
- Contents
- Review Article
- How to Improve Sustainability and Environmentally Friendly Behaviour in Automatic Dishwashing? Example: Germany
- Physical Chemistry
- αs-Casein-PE6400 Mixtures: Thermodynamics of Micelle Formation
- Effect of Alcohols on Phase Stability of Ionic Liquid Microemulsions
- The Effect on Solution Properties of Replacing a Hydrogen Atom with a Methyl Group in a Surfactant
- Application
- New Approach of Sucrose Myristate as a Promising Penetration Enhancer in Dermal Preparations
- Environmental Chemistry
- Identification of Non-ionic Surfactants in Elements of the Aquatic Environment
- Synthesis
- Synthesis and Properties of 1,2,3,4-Butanetetracarboxylic Acid Type Gemini Surfactants with Semifluoroalkyl Chain as Hydrophobic Group
- Solvent Free Synthesis of Four Cationic Surfactants: Evaluation of Their Corrosion Inhibition Properties on Zinc Phosphate Conversion Coating on Mild Steel
- Synthesis and Spectrophotometric Study of Toxic Metals Extraction by Novel Thio-Based Non-Ionic Surfactant
- Analysis
- Eco-favourable Mobile Phase in Thin Layer Chromatographic Analysis of Surfactants: Resolution of Coexisting Alkyl Dimethylbenzyl Ammonium Chloride, Cetyltrimethyl Ammonium Bromide and Triton X 100
Artikel in diesem Heft
- Contents/Inhalt
- Contents
- Review Article
- How to Improve Sustainability and Environmentally Friendly Behaviour in Automatic Dishwashing? Example: Germany
- Physical Chemistry
- αs-Casein-PE6400 Mixtures: Thermodynamics of Micelle Formation
- Effect of Alcohols on Phase Stability of Ionic Liquid Microemulsions
- The Effect on Solution Properties of Replacing a Hydrogen Atom with a Methyl Group in a Surfactant
- Application
- New Approach of Sucrose Myristate as a Promising Penetration Enhancer in Dermal Preparations
- Environmental Chemistry
- Identification of Non-ionic Surfactants in Elements of the Aquatic Environment
- Synthesis
- Synthesis and Properties of 1,2,3,4-Butanetetracarboxylic Acid Type Gemini Surfactants with Semifluoroalkyl Chain as Hydrophobic Group
- Solvent Free Synthesis of Four Cationic Surfactants: Evaluation of Their Corrosion Inhibition Properties on Zinc Phosphate Conversion Coating on Mild Steel
- Synthesis and Spectrophotometric Study of Toxic Metals Extraction by Novel Thio-Based Non-Ionic Surfactant
- Analysis
- Eco-favourable Mobile Phase in Thin Layer Chromatographic Analysis of Surfactants: Resolution of Coexisting Alkyl Dimethylbenzyl Ammonium Chloride, Cetyltrimethyl Ammonium Bromide and Triton X 100
