Synthesis, Properties and Applications of Anionic Phosphate Ester Surfactants: A Review

Pinklesh Arora; Rakhi Singh; Geetha Seshadri; Ajay Kumar Tyagi

doi:10.3139/113.110570

Artikel

Synthesis, Properties and Applications of Anionic Phosphate Ester Surfactants: A Review

Pinklesh Arora , Rakhi Singh , Geetha Seshadri und Ajay Kumar Tyagi

Veröffentlicht/Copyright: 11. Juli 2018

Veröffentlicht von

Veröffentlichen auch Sie bei De Gruyter Brill

Manuskript einreichen Informationen für Autor*innen

Aus der Zeitschrift Tenside Surfactants Detergents Band 55 Heft 4

Abstract

This paper reviews the various technologies involved in the synthesis of anionic phosphate ester surfactants. Use of base material such as alcohol ethoxylates, alkyl phenol ethoxylates, fatty acid ethoxylates and phosphating reagents plays a key role on the applications and properties of phosphate ester surfactants. Also roles are played by the reaction conditions maintained and charging conditions on the mono-diester ratio. In this paper attempt has been made to review the base materials used for the synthesis of phosphate esters, synthesis processes and their effect on the properties of phosphate esters, applications and global scenario of phosphate ester surfactants.

Kurzfassung

In diesem Artikel werden die verschiedenen Technologien, die bei der Synthese anionischer Phosphatester-Tenside eine Rolle spielen, dargestellt. Die Verwendung der Ausgangsmaterialien wie Alkoholethoxylate, Alkylphenolethoxylate, Fettsäureethoxylate und Phosphatierungsreagenzien spielt eine Schlüsselrolle bei den Anwendungen und Eigenschaften von Phosphatestertensiden. Auch spielen die beibehaltenen Reaktionsbedingungen und Aufladungsbedingungen auf das Mono-Diester-Verhältnis eine Rolle. In dieser Arbeit wurde versucht, die für die Synthese von Phosphatestern verwendeten Ausgangsmaterialien, Syntheseprozesse und ihre Wirkung auf die Eigenschaften von Phosphatestern, Anwendungen und das globale Szenario von Phosphatestertensiden zu überprüfen.

Key words: Phosphate esters; surfactants; alcohol ethoxylates; phosphation

Stichwörter: Phosphatester; Tenside; Alkoholethoxylate; Phosphatierung

*Correspondence address, Dr. Pinklesh Arora, Shriram Institute for Industrial Research, 19 University Road, Delhi – 110007, India, Tel.: +911127667267, Fax: +911127667676, E-Mail: pinklesh@shriraminstitute.org

Dr. Pinklesh Arora, has done her Ph.D. in 2009 from C.C.S. University, Meerut, India. She has 11 years experience in Shriram Institute for Industrial Research, Delhi, India in the field of surfactants, polymers, polymer nanocomposites and adhesives. She has been worked on various national and international R & D projects. She has authored one book, five research papers and five conference papers in her credit.

Dr. Rakhi Singh has done her Ph.D. from B.R. Ambedkar University, Agra, India in 2007. She has got 11 years experience in Shriram Institute for Industrial Research, Delhi, India as Scientist in the field of development and modification of surfactants, optical polymers, perm-selective membranes and analytical chemistry. She has also research experience on method development and validations of various national and international R & D projects. She has authored two chapters in book, two research papers and four conference papers in her credit.

Dr. Geetha Seshadri, Assistant Director & Chief, has done her Ph.D. from Dr. B. R. Ambedkar University, Agra, India in 2001. She has 22 years research experience in the areas of fluoropolymers, surfactants, optical polymers, polymer nanocomposites, block co-polymers & tetrazole, perm-selective membranes and lubricants etc. She has authored one book, more than 30 research and conference papers and 13 patents. She has headed various research projects from national and international agencies.

Dr. Ajay Kumar Tyagi, Senior Assistant Director & Chief and Head of the Department, Material Science Division has 33 years of research experience. He has completed his Ph.D in 1998 from Kanpur University, Kanpur, India. His research experience is exclusively in the fields of polymer synthesis and their modifications such as polylactide, polyglycolide, glycolide-caprolactone copolymers, styrene – butadiene – styrene triblock copolymer, perfluorinated lubricating oil from hexafluoro propylene as radiation resistant materials, polyurethane based perm selective membranes, dry lubricants, adhesives and derivatization of natural polymers etc. He has executed various national and international research projects. He has published more than 35 research papers in national and international journals and five patents. He is a member of Association of Carbohydrate Chemists and Technologists (India).

References

1. http://www.elementisspecialties.com/esweb/esweb.nsf/pages/surfactants-anionicsurfactantsSuche in Google Scholar

2. Williamson, S. C.: Cleansing compositions comprising ethoxylated alcohol monoesters of phosphoric acid, U.S. Patent 4493782 (1985).Suche in Google Scholar

3. Report on “North America Phosphate Esters Market: By Type (Tri Aryl/Alkyl Aryl Phosphate Esters, Tri Alkyl Phosphate Ester and Bisphosphates); By Application (Lubricants, Surfactants, Pesticides, Fire Retardants, Hydraulic Fluids, Plasticizers, Paints & Coatings, and Others); By Geography (U.S., Canada, and Mexico) – Forecasts till 2020”, 2016, Report Code-PH1001.Suche in Google Scholar

4. Derian, P. J., Tao, G., Herve, P. J. C. and Reierson, R. L.: High solids, pumpable aqueous compositions of high monoalkyl phosphate ester salt content, U.S. Patent 6262130 (2001).Suche in Google Scholar

5. http://www.elementisspecialties.com/esweb/esweb.nsf/pages/surfactants-anionicsurfactants.Suche in Google Scholar

6. Reierson, R. L., Crooks, R., Gabbianelli, A. and Warburton, S.: Phosphate Esters: A natural for personal care and cosmetic applications, Cosmetic Science Technology, T4 International, Hertfordshire (2006) 267–274.Suche in Google Scholar

7. https://biokhimact.com.ua/images/catalogs/Surfactants.pdf.Suche in Google Scholar

8. http://www.rimpro-india.com/articles1/surfactants-widely-used-in-industrial-processes-fatty-alcohol-ethoxylate,-fatty-acid-ethoxylate.html.Suche in Google Scholar

9. https://sites.google.com/site/demulsifiers/home/fatty-alcohol-ethoxylate-fatty-acid-ethoxylate-surfactants-for-industries.Suche in Google Scholar

10. Tracy, D. J. and Reierson, R. L.: Phosphate ester surfactants, Handbook of Detergents Part F: Production, Surfactant Science Series, edited by U.Zoller and P.Sosis, CRC Press, Boca Raton, Florida, USA, 142 (2009) 183–199. 10.1201/9781420014655Suche in Google Scholar

11. Tadashi, H., Method for producing copolymerizable compound containing functional group of phosphoric acid, US 3686371 A, 1972.Suche in Google Scholar

12. Reierson, R. L.: Phosphation reagent, US 6136221 A, 2000.Suche in Google Scholar

13. Thilo, V. E. and Sauer, R.: On the chemistry of condensed phosphates and arsenates. XVII. The course and products of dehydration of monophosphoric acid H₃PO₄, J. Prakl. Chem.4 (1957) 324–348. 10.1002/prac.19570040512Suche in Google Scholar

14. Clarke, F. and Lyons, J.: The alcoholysis of polyphosphoric acid, J. Am. Chem. Soc., 88 (1966) 4401–4405. 10.1021/ja00971a018Suche in Google Scholar

15. Nelson, A. K. and Toy, A. D. F.: The preparation of long-chain monoalkyl phosphates from pyrophosphoric acid and alcohols, Inorganic Chemistry2 (1963) 775–777. 10.1021/ic50008a026Suche in Google Scholar

16. Tracy, D. J. and Reierson, R. L.: Commercial synthesis of monoalkyl phosphate, J. Surfactants and Detergents5 (2) (2002) 169–172. 10.1007/s11743-002-0218-9Suche in Google Scholar

17. P. E.Slade: Handbook of Fiber Finish Technology, Gulf Research Associate295 (1997).Suche in Google Scholar

18. Kurosaki, T. and Manb, A.: Method for producing a phosphoric monoester, US Patent 4350645, (1982).Suche in Google Scholar

19. AkiraM., Akira, F.Shinji, T., Toshio, N. and MasayukiU.: Process for the preparation of phosphoric monoester, US Patent 6034261 A, 2000.Suche in Google Scholar

20. http://infohouse.p2ric.org/ref/33/32804.pdf.Suche in Google Scholar

21. Leslie R.Rudnick: Lubricant Additives: Chemistry and applications, CRC Press, USA; 2003, 45–71. 10.1201/9780824747404Suche in Google Scholar

22. Bocnig, I. A., Crutchfield, M. M. and HeitchC. W.: Phosphoric acid and Phosphates, Kirk-Othmer Encyclopedia of Chemical Technology, 3^rd edn.John Wiley & Sons, New York, 17 (1982) 518. 10.1002/0471238961.1608151907011804.a01Suche in Google Scholar

23. Williamson, S. C.: Cleansing compositions comprising ethoxylated alcohol monoesters of phosphoric acid, US Patent 4493782, 1985.Suche in Google Scholar

24. Loraine, C. P., Alvino, G. and Reierson, R. L.: Aqueous surfactant compositions of monoalkyl phosphate ester salts and amphoteric surfactants, US Patent-6566408 B1, (2003).Suche in Google Scholar

25. Katz, M. M., Hashem, M. M. and Talley, C. P.: Method of removing dioxane from phosphate ester surfactants, US Patent 4375437 A (1983).Suche in Google Scholar

26. Reierson, R. L.: Phosphorylation agent, process and use, EP 0675076 A2 (2002).Suche in Google Scholar

27. Reierson, R. L.: Monoalkyl phosphonic acid ester production process, US Patent US 5554781 A (1996).Suche in Google Scholar

28. Reierson, R. L.: In-situ phosphation reagent process, US Patent 5550274 A (1996).Suche in Google Scholar

29. Reierson, R. L.: Phosphation reagent, process and use, EP 1207135 B1 (2008).Suche in Google Scholar

30. HanpingLi, YongJin, BaozhuFan, RuiQi, XinfengCheng and ShaojunPeng: Journal of Dispersion Science & Technology38 (5) (2017). 10.1080/01932691.2016.1192041Suche in Google Scholar

31. ShinjiT., Kengo, S. and Kiyoshi, A.: Process for the preparation of phosphoric monoester, US Patent 5883280 A (1999).Suche in Google Scholar

32. Reierson, Robert L.: Process of making low dioxane alkoxylate phosphate esters, US Patent 5463101 A (1995).Suche in Google Scholar

33. Ren, L. F., Wang, X. C., Qiang, T. T. and An, H. R.: Synthesis of amphoteric phosphate ester surfactant by polyphosphoric acid and its application in free-chrome collagen fiber, Advanced Materials Research, 129–131 (2010) 271–275. 10.4028/www.scientific.net/AMR.129-131.271Suche in Google Scholar

34. Johnson, D. W. and Hils, J. E.: Phosphate esters, thiophosphate esters and metal thiophosphates as lubricant additives, Lubricants1 (4) (2013) 132–148. 10.3390/lubricants1040132Suche in Google Scholar

35. Imokawa, G.: Study on skin-irritating and biological properties of monoalkyl phosphate anionic surfactants, J. Am. Oil Chem. Soc.56 (1979) 604–609. 479492 10.1007/bf02660246Suche in Google Scholar PubMed

36. WittW. J. D.: Four corners, J. Am. Oil Chem. Soc.49 (1972) 362–370. 10.1007/BF02628902Suche in Google Scholar

37. http://surchem.pl/pl/kosmetyki/pdf/Lieferprogramm_Phosphate%20Esters.pdfSuche in Google Scholar

38. Ghesner, I. and Horton, D. P.: Gelled hydrocarbons for oilfield processes, phosphate ester compounds useful in gellation of hydrocarbons and methods for production and use thereof, US Patent-7972996 B2, (2011).Suche in Google Scholar

39. Phillips, W. D.: Phosphate ester hydraulic fluids, Handbook of Hydraulic Fluid Technology, IInd Edition, CRC Press, 833–891 (2011). 22128728 10.1201/b11225-20Suche in Google Scholar

40. Fogel, A. W.: Neutralization of phosphate esters, compositions based upon and methods using same, US Patent-6417238 B1 (2002).Suche in Google Scholar

41. Fogel, A. W.: Neutralization of phosphate esters, compositions based upon and methods using same, US Patent-6828352 B2 (2004).Suche in Google Scholar

42. Hall, S. A. and Jacobson, M.: Hexaethyl tetraphosphate and tetraethyl pyrophosphate, Ind. Eng. Chem., 40 (1948) 694–699. 10.1021/ie50460a024Suche in Google Scholar

43. Cefn, B. and Antonie, W. J.: Fog reduction in polyurethane foam using phosphate esters, US Patent-5958993 (1999).Suche in Google Scholar

44. Magendie, Franke: Weidnann Ulrich, Flame-proofing agents, US Patent-7053138 B2 (2006).Suche in Google Scholar

45. Paul, M.: Aryl phosphate ester fire-retardant additive for low-smoke vinyl applications, J. Vinyl and Additive Technology10 (2004) 187–192. 10.1002/vnl.20028Suche in Google Scholar

46. Haak, J. L. and Mohr, P. H.: Organophosphate-containing antifreeze, US Patent-4613445 (1986).Suche in Google Scholar

47. Pereira, A. G., Obukowho, P., Garcia, M. G. and King, N.: Fatty alcohol phosphate ester emulsifier compositions, US Patent-6117915 A (2000).Suche in Google Scholar

48. John, I. and JohnH.: Alkoxylated silicone phosphate esters as emulsifiers, US Patent-5382381 A (1995).Suche in Google Scholar

49. Spencer, V. E. and Stewart, R.: Phosphate studies: I. soil penetration of some organic and inorganic phosphates, Soil Sci.38 (1) (1934) 65–79. 10.1097/00010694-193407000-00005Suche in Google Scholar

50. Bancroft, W. D., Rutzler, J. E. and Wilson, J. K.: Soluble organic phosphate fertilizer materials, USP-2213513 A (1940).Suche in Google Scholar

51. Konzak, C. F. and Polle, E. A.: Processes for producing ethylene glycol phosphate esters and foliar fertilizers containing same, US Patent-5372627 A (1994).Suche in Google Scholar

52. Konzak, C. F. and Polle, E. A.: Foliar phosphate fertilizers, US Patent-6436165 B1 (2002).Suche in Google Scholar

53. Donald, H. Lorenz and Williams, E. P.: Method of emulsion polymerization using phosphate esters of normal alkanols as surfactant, US Patent-3963688 A (1976).Suche in Google Scholar

54. Philip, M. and Edwards, D.: Phosphate ester lubricants, EP-0349093 B1 (1992).Suche in Google Scholar

55. Peter, D.: Regeneration of phosphate ester lubricating fluids, US Patent 5661117 A (1997).Suche in Google Scholar

56. Brown, K.: Condition-monitoring of phosphate ester hydraulic fluids, machinery lubrication, http://www.machinerylubrication.com/Read/424/phosphate-ester-hydraulic-fluidsSuche in Google Scholar

57. MartinR. L.: Reaction product of nitrogen bases and phosphate esters as corrosion inhibitors, US Patent 5380466 A (1995).Suche in Google Scholar

58. Person, H. K. L., Besse, M. E., Schmidt, B. E. and Sykes, C. S.: Alkyl ether amine conveyor lubricants containing corrosion inhibitors, WO/1997/045509 A1 (1997).Suche in Google Scholar

59. Martin, T. W.: Pigmented inkjet inks containing phosphated ester derivatives, US patent 5972089 A (1999).Suche in Google Scholar

60. Martin, T. W., Pigmented inkjet inks containing phosphated ester derivatives, EP-848045 B1 (2001).Suche in Google Scholar

61. Omatsu, T. and Kawauchi, K.: Water based pigment ink composition, US patant-2005234150 A1 (2005).Suche in Google Scholar

62. Barr, D. B., Bravo, R., Weerasekera, G., Caltabiano, L. M., Whitehead, R. D., Jr., Olsson, A. O., Caudill, S. P., Schober, S. E., Pirkle, J. L., Sampson, R. J. and Needham, L. L.: Concentrations of dialkyl phosphate metabolites of organophosphorus pesticides in the U.S. population, Environ. Health Perspect.112 (2004) 186–200. 14754573 10.1289/ehp.6503Suche in Google Scholar PubMed PubMed Central

63. Report on Phosphate Ester Market by Type (Triaryl Phosphate Esters, Trialkyl Phosphate Esters, Alkyl Aryl Phosphate Ester), Application (Lubricants, Surfactants, Pesticides, Fire Retardants), Region (North America, Europe, Asia-Pacific) – Global Forecast to 2022, Report Code: CH 4050, 2017.Suche in Google Scholar

64. http://www.mrrse.com/phosphate-esters-marketSuche in Google Scholar

Received: 2018-01-18

Accepted: 2018-03-16

Published Online: 2018-07-11

Published in Print: 2018-07-16

Sie haben derzeit keinen Zugang zu diesem Inhalt.

Artikel in diesem Heft

https://doi.org/10.3139/113.110570

Schlagwörter für diesen Artikel

Phosphate esters; surfactants; alcohol ethoxylates; phosphation