Arginine Based Novel Cationic Surfactants: A Review
-
Ayushi Singh
und Vinod K. Tyagi
Abstract
Conventional surfactants are chemical species derived from various feed stocks and are consumed in large quantities for wide spread household as well as industrial applications. As most of the conventional surfactants have many limitations such as toxicity to humans and adverse effect on environment, the development of less irritant, less toxic, consumer-friendly surfactants is of immense importance. Arginine based surfactants, therefore, constitute a novel class of surfactants produced from renewable raw materials and can be seen as an alternative to conventional surfactants. Arginine based surfactants have good antimicrobial activity, good biodegradability and less human and aquatic toxicity. This review paper deals with the synthesis of different class of arginine based surfactants. Besides this, different biological and surface active properties of arginine based surfactants have also been described.
Kurzfassung
Bei den konventionellen Tensiden handelt es sich um chemische Verbindungen, die aus unterschiedlichen Ausgangsmaterialien erzeugt wurden. Sie werden in großen Mengen sowohl für Anwendungen im Haushalt als auch in der Industrie verbraucht. Da die meisten konventionellen Tenside viele Einschränkungen aufgrund der Toxizität gegenüber Menschen und der negativen Auswirkungen für die Umwelt haben, ist die Entwicklung von weniger irritierenden, weniger toxischen und verbraucher-freundlicheren Tensiden von sehr großer Bedeutung. Auf Arginin basierende Tenside stellen daher eine neue Tensidgruppe dar, die aus erneuerbaren Rohmaterialien erzeugt wird und als eine Alternative zu den konventionellen Tensiden angesehen werden kann. Sie besitzen gute antimikrobielle Aktivitäten, sind gut biologisch abbaubar und zeigen eine geringe humane und aquatische Toxizität. Dieser Übersichtsartikel behandelt die Synthese verschiedener Gruppen der auf Arginin basierenden Tenside. Des Weiteren werden ebenfalls verschiedene biologische und oberflächenaktive Eigenschaften dieser Tenside dargestellt.
References
1. Macia, M., Seguer, J., Infante, M. R., Selve, C. and Vinardell, M. P.: Toxicology106 (1996) 1. 10.1016/0300-483X(95)03131-XSuche in Google Scholar
2. Baschang, G., Hartmann, A. and Wacker, O.: US patent 4666886 A (1987).Suche in Google Scholar
3. Braun, D. B.: Cosmetics and Toiletries104 (1989) 89.Suche in Google Scholar
4. Yokota, H., Sagawa, K., Eguchi, Ch. and Takehara, M.: J. Am. Oil Chem. Soc.62 (1985) 1719. 10.1007/BF02541673Suche in Google Scholar
5. Perez, L., Torres, J. L., Manresa, A., Solans, C. and Infante, M. R.: Langmuir12 (1996) 5301. 10.1021/la9509357Suche in Google Scholar
6. Infante, M. R., Pinazo, A., Molinero, J., Seguer, J. and Vinardell, P., in: Protein-Based Surfactants, Marcel Dekker, New York101 (2001) 167.Suche in Google Scholar
7. Perez, L., Garcia, M. T., Ribosa, I., Vinardell, M. P., Manresa, M. A. and Infante, M. R.: Environ. Toxicol. Chem.21 (2002) 1285. 10.1002/etc.5620210624Suche in Google Scholar
8. Piera, E., Infante, M. R. and Clapes, P.: Biotechnol. Bioeng.70 (2000) 331. 10.1002/1097-0290(20001105)70:3<323::AID-BIT9>3.0.CO;2-NSuche in Google Scholar
9. Clape's, P. and Infante, M. R.: Biocatal. Biotransform.20 (2002) 233. 10.1080/10242420290004947Suche in Google Scholar
10. Pinazo, A., Wen, X., Perez, L., Infante, M. R. and Franses, E. I.: Langmuir15 (1999) 3142. 10.1021/la981295lSuche in Google Scholar
11. Infante, M. R., Molinero, J., Bosch, P., Juliá, Ma. R. and Erra, P.: J. Am. Oil Chem. Soc.69 (1992) 652. 10.1007/BF02635804Suche in Google Scholar
12. Piera, E., Comelles, F., Erra, P. and Infante, M. R.: J. Chem. Soc. Perkin Trans.2 (1998) 342.Suche in Google Scholar
13. Clapés, P., Morán, C. and Infante, M. R.: Biotechnol. Bioeng.63 (1999) 343. 10.1002/(SICI)1097-0290(19990505)63:3<333::AID-BIT10>3.0.CO;2-GSuche in Google Scholar
14. Valivety, R., Gill, I. S. and Vulfson, E. N.: J. Surf. Deterg.1 (1998) 185. 10.1007/s11743-998-0017-3Suche in Google Scholar
15. Soo, E. L., Salleh, A. B., Basri, M., Rahman, R. N. Z. R. A. and Kamaruddin, K.: J. Biosci. Bioeng.95 (2003) 361. 10.1016/S1389-1723(03)80068-3Suche in Google Scholar
16. Solans, C., Infante, M. R., Azemar, N. and Warnheim, T.: Prog. Colloid Polym. Sci.79 (1989) 75.Suche in Google Scholar
17. Solans, C., Pres, M. A., Azemar, N. and Infante, M. R.: Progr. Coll. Polym. Sci.81 (1990) 150.Suche in Google Scholar
18. Moran, C., Clapes, P., Comelles, F., García, M. T., Perez, L., Vinardell, P. and Infante, M. R.: Langmuir17 (2001) 5075. 10.1021/la010375dSuche in Google Scholar
19. Moran, C., Pinazo, A., Clapes, P., Perez, L., Vinardell, M. P. and Infante, M. R.: Green Chem.6 (2004) 240. 10.1039/b400293hSuche in Google Scholar
20. Infante, M. R., Perez, L., Pinazo, A., Clapes, P., Moran, M. C., Angelet, M., García, M. T. and Vinardell, M. P.: C. R. Chim.7 (2004) 592. 10.1016/j.crci.2004.02.009Suche in Google Scholar
21. Fordedal, H., Sjoblolm, S. and Infante, M. R.: Colloids Surf.A 79 (1993) 88. 10.1016/0927-7757(93)80162-8Suche in Google Scholar
22. Infante, M. R., Pinazo, A. and Seguer, J.: Colloids Surf.A 49 (1997) 124.Suche in Google Scholar
23. McGrath, K. M.: Langmuir11 (1995) 1839. 10.1021/la00005a066Suche in Google Scholar
24. Laughlin, R. G., in: Cationic Surfactants: Physical Chemistry, P. M., Holland, (Eds.), Marcel Dekker Inc.: New York2 (1991) 40.Suche in Google Scholar
25. Kunieda, H., Nakamura, K., Infante, M. R. and Solans, C.: Adv. Mater.4 (1992) 293. 10.1002/adma.19920040411Suche in Google Scholar
26. Infante, M. R., Molinero, J., Erra, P., Julia, M. R. and Garcia Dominguez, J. J.: Fette Wissenschaft Technologie87 (1985) 314.Suche in Google Scholar
27. Moran, C., Infante, M. R. and Clapes, P.: J. Chem. Soc., Perkin Trans.1 (2001) 2070.Suche in Google Scholar
28. Rosen, M. J. and Tracy, D. J.: J. Surfact. Deter.1 (2001) 554.Suche in Google Scholar
29. Menger, F. M. and Keiper, J. S.: Angew. Chem. Int. Ed.39 (2000) 1920. 10.1002/1521-3773(20000602)39:11<1906::AID-ANIE1906>3.0.CO;2-QSuche in Google Scholar
30. Pinazo, A., Wen, X., Perez, L., Infante, M. R. and Franses, E. I.: Colloid SurfaceA 189 (2001) 235. 10.1016/S0927-7757(01)00595-7Suche in Google Scholar
31. Devinsky, F., Lacko, I., Bittererova, F. and Mlynarcik, D.: Chem. Papers.41 (1987) 814.Suche in Google Scholar
32. Moran, C., Infante, M. R. and Clapes, P.: J. Chem. Soc., Perkin Trans.1 (2001) 2070.Suche in Google Scholar
33. Garcia, M. T., Ribosa, I., Guindulain, T., Sanchez Leal, J. and Vives-Rego, J.: Environ. Pollut.111 (2001) 175. 10.1016/S0269-7491(99)00322-XSuche in Google Scholar
34. Okamoto, V., Ohkoshi, K., Itakagaki, H., Tsuda, T., Kakishima, H., Ogawa, T., Kasai, Y., Ohuchi, J., Kojima, H., Kurishita, A., Kaneko, T., Matsushima, Y., Iwabuchi, Y. and Ohno, Y.: Toxicol. in vitro.13 (1999) 124. 10.1016/S0887-2333(98)00066-6Suche in Google Scholar
35. Krog, N. J. and Friberg, S. E., in: Larsson, K. (ed.) Food Emulsions, Marcel Dekker, New York3rd ed.4 (1997) 188.Suche in Google Scholar
36. Krog, N. J., Gunstone, F. D. and Padley, F. B.: Lipid Technologies and Applications, Marcel Dekker, New York20 (1997) 534.Suche in Google Scholar
37. Perez, L., Pinazo, A., García, M. T., Moran, M. C. and Infante, M. R.: New J. Chem.28 (2004) 1334. 10.1039/b405733cSuche in Google Scholar
38. Pinazo García, M. T., Moran, M. C. and Infante, M. R.: C. R. Chimie.14 (2011) 735.Suche in Google Scholar
39. Moran, M. C., Pinazo, A., Perez, L., Clapes, P., Pons, R. and Infante, M. R.: C. R. Chim.7 (2004) 176.Suche in Google Scholar
40. Perez, L., Clapes, P., Pinazo, A., Angelet, M.Vinardell, M. P. and Infante, M. R.: New J. Chem.26 (2002) 1227. 10.1039/b200164kSuche in Google Scholar
41. Perez, L., Infante, M. R., Pons, R., Moran, M. C., Vinardell, M. P., Mitjans, M. and Pinazo, A.: Colloids Surf.B 35 (2004) 242. 10.1016/j.colsurfb.2004.03.014Suche in Google Scholar PubMed
42. Moran, M. C., Pinazo, A., Clapes, P., Perez, L., Infante, M. R. and Pons, R.: Phys. Chem.108 (2004) 11088.Suche in Google Scholar
43. Benavides, T., Martinez, V., Mitjans, M., Infante, M. R., Moran, M. C., Clapes, P., Clothier, R. and Vinardell, M. P.: Toxicology201 (2004) 93. 10.1016/j.tox.2004.04.003Suche in Google Scholar PubMed
44. Valivety, R., Jauregui, P. and Vulfson, E. N.: J. Am. Oil Chem. Soc.74 (1997) 886. 10.1007/s11746-997-0232-8Suche in Google Scholar
45. Mitin, Y. V., Braun, K. and Kuhl, P.: Biotechnol. Bioeng.54 (1998) 290.Suche in Google Scholar
46. Rosen, M. J., in: Surfactants and Interfacial Phenomena, 3rd ed., Wiley-Interscience, Hoboken, NJ (2004) 64. 10.1002/0471670561Suche in Google Scholar
47. Pinazo, A., Perez, L., Infante, M. R. and Pons, R.: Phys. Chem.6 (2004) 1481.Suche in Google Scholar
48. Perez, L., Infante, M. R., Angelet, M., Clapès, P. and Pinazo, A.: Prog. Colloid Polym. Sci.123 (2004) 216.Suche in Google Scholar
49. Lozano, N., Pinazo, A., La Mesa, C., Pèrez, L.Andreozzi, P. and Pons, R.: J. Phys. Chem. B113 (2009) 6327. 10.1021/jp810671pSuche in Google Scholar PubMed
50. Albalat, R., Claret, J., Ignès-Mullol, J., Sagues, F., Morän, C., Pèrez, L., Clapès, P. and Pinazo, A.: Langmuir19 (2003) 10884. 10.1021/la035281dSuche in Google Scholar
51. Lozano, N., Pinazo, A., Pèrez, L. and Pons, R.: Langmuir26 (2010) 2566. 10.1021/la902850jSuche in Google Scholar PubMed
52. Lozano, N., Pinazo, A., Pons, R., Pèrez, L. and Franses, E. I.: Colloids Surf.B 74 (2009) 74. 10.1016/j.colsurfb.2009.06.020Suche in Google Scholar PubMed
53. Perez, N., Pèrez, L., Infante, M. R. and Garcıa, M. T.: Green Chem.7 (2005) 546. 10.1039/b419204dSuche in Google Scholar
54. Vinardell, M. P., Benavides, T., Mitjans, M., Infante, M. R., Clapes, P. and Clothier, R.: Food Chem. Toxicol.46 (2008) 3841. 10.1016/j.fct.2008.10.007Suche in Google Scholar PubMed
55. Infante, M. R., Miguel, M. G. and Lindman, B.: Langmuir22 (2006) 88. 10.1021/la052036gSuche in Google Scholar PubMed
56. Infante, M. R., Moran, M. C., Miguel, M. G. and Lindman, B.: Colloids Surf.A 301 (2007) 375.Suche in Google Scholar
57. Infante, M. R., Penacho, N., Simoes, S., Lima, M. C. P., Lindman, B. and Miguel, M. G.: Mol. Membr. Biol.25 (2008) 34.Suche in Google Scholar
58. Moran, M. C., Miguel, M. G., Lindman, B., Infante, M. R. and Pons, R: Langmuir26 (2010) 60. 10.1021/la100818pSuche in Google Scholar PubMed
59. Castillo, J. A., Pinazo, A., Carilla, J., Infante, M. R.Alsina, M. A., Haro, I. and Clapes, P.: Langmuir20 (2004) 3387. 10.1021/la036452hSuche in Google Scholar PubMed
60. Infante, M. R., Pinazo, A. J., Molinero, J., Seguer, J. and Vinardell, P., in: Protein-Based Surfactants. Marcel Dekker: New York101 (2001) 167.Suche in Google Scholar
61. Pèrez, L., Pinazo, A., Rosen, M. J. and Infante, M. R.: Langmuir14 (1998) 2315. 10.1021/la971135uSuche in Google Scholar
62. McDonnell, G. and Russel, A. D.: Clin. Microbiol.12 (1999) 179.Suche in Google Scholar
63. Oren, Z., Hong, J. and Shai, Y.: J. Biol. Chem.272 (1997) 14649. 10.1074/jbc.272.23.14643Suche in Google Scholar PubMed
© 2014, Carl Hanser Publisher, Munich
Artikel in diesem Heft
- Contents/Inhalt
- Contents
- Abstracts
- Abstracts
- Review Article
- Arginine Based Novel Cationic Surfactants: A Review
- Application
- Selection of Surfactants on the Basis of Foam and Emulsion Properties to Obtain the Fire Fighting Foam and the Degreasing Agent
- Negative Synergistic Effect on Foaming in Body Care Products with Silicone Oil and the Needle-Like Crystal of Ethylene Glycol Distearate
- Technical Chemistry
- Wetting Ability in Aqueous Mixtures of Amine Oxide with Anionic and Nonionic Surfactants
- Environmental Chemistry
- Validation of an HPLC Method for Determining log Pow Values of Surfactants
- Removal of Lead From Aqueous Media Using Carbonized and Acid Treated Orange Peel
- Corrosion and Scale Inhibition Properties by Phosphate-free and Nitrogen-free Scale Inhibitor in Cooling Water System
- Preparation and Application of Fluorescent-tagged Inhibitor for Calcium Phosphate and Iron(III) Hydroxide Scales in Industrial Cooling Water Systems
- Novel Surfactants
- Effect of Tuned Head Polarity of Cetyl Trimethyl Ammonium Bromide on their Physicochemical Properties
- Physical Chemistry
- Aggregation Behavior of PEO-PPO-PEO Tri-Block Copolymer (Pluronic®L64) in Nonionic Surfactant Additives Environment
- Surfactant Processing
- Solidification of Surfactants and Detergents to Dust-Free Free Flowing Pastilles
Artikel in diesem Heft
- Contents/Inhalt
- Contents
- Abstracts
- Abstracts
- Review Article
- Arginine Based Novel Cationic Surfactants: A Review
- Application
- Selection of Surfactants on the Basis of Foam and Emulsion Properties to Obtain the Fire Fighting Foam and the Degreasing Agent
- Negative Synergistic Effect on Foaming in Body Care Products with Silicone Oil and the Needle-Like Crystal of Ethylene Glycol Distearate
- Technical Chemistry
- Wetting Ability in Aqueous Mixtures of Amine Oxide with Anionic and Nonionic Surfactants
- Environmental Chemistry
- Validation of an HPLC Method for Determining log Pow Values of Surfactants
- Removal of Lead From Aqueous Media Using Carbonized and Acid Treated Orange Peel
- Corrosion and Scale Inhibition Properties by Phosphate-free and Nitrogen-free Scale Inhibitor in Cooling Water System
- Preparation and Application of Fluorescent-tagged Inhibitor for Calcium Phosphate and Iron(III) Hydroxide Scales in Industrial Cooling Water Systems
- Novel Surfactants
- Effect of Tuned Head Polarity of Cetyl Trimethyl Ammonium Bromide on their Physicochemical Properties
- Physical Chemistry
- Aggregation Behavior of PEO-PPO-PEO Tri-Block Copolymer (Pluronic®L64) in Nonionic Surfactant Additives Environment
- Surfactant Processing
- Solidification of Surfactants and Detergents to Dust-Free Free Flowing Pastilles