Study on Skin‐Irritating and Biological Properties of Monoalkyl Phosphate Anionic Surfactants

Imokawa, Genji

doi:10.1007/bf02660246

Cited by 9 publications

(5 citation statements)

References 11 publications

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“…1,2-Epoxytetradecane (6.37 g, 30 mmol, 1 14 ) was reacted with phosphorylation agent (48 mol% diethyl phosphate (DEP), 4.58 g, 33 mmol) at 60-70°C. After a 2-h reaction, 5.4 ml (0.3 mol) of water was added with stirring in order to hydrolyze the diethyl phosphate ester 5 14 , which was not isolated. The solution was diluted with toluene, and the toluene layer was washed with water.…”

Section: Preparation Of Raw Materialsmentioning

confidence: 99%

“…The preparation of the 2-hydroxy tetradecyl phosphate homologue 6 14 is described here as an example. 1,2-Epoxytetradecane (6.37 g, 30 mmol, 1 14 ) was reacted with phosphorylation agent (48 mol% diethyl phosphate (DEP), 4.58 g, 33 mmol) at 60-70°C. After a 2-h reaction, 5.4 ml (0.3 mol) of water was added with stirring in order to hydrolyze the diethyl phosphate ester 5 14 , which was not isolated.…”

Section: Preparation Of Raw Materialsmentioning

confidence: 99%

“…Specifically, monoalkyl phosphate (MAP) has been playing a key role in the toiletry industry in personal-care products. Because of their compatibility with skin and inherent lowirritation characteristics, they have been significantly used in toiletry applications, such as cleansers, body and hair shampoos, and oral care formulations [2,[13][14][15].…”

Section: Introductionmentioning

confidence: 99%

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Preparation and Properties of Phosphate Surfactants Containing Ether and Hydroxy Groups

Osanai

Yamada

Hidano

et al. 2009

J Surfact & Detergents

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Phosphate surfactants containing ether and hydroxyl groups were prepared by a simple reaction between the corresponding epoxide and the diethyl phosphate. The relationships between the structure and colloidal properties were evaluated in terms of the critical micelle concentration (CMC), cCMC, foaming ability, and water absorbing and holding abilities. Based on these results, it was concluded that the ether and hydroxy groups synergistically worked together to decrease the CMC and increase the foaming ability. The degree of neutralization remarkably affected the colloidal properties. The highly neutralized states showed a more positive effect on water holding power but an opposite effect on the foaming ability.

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Section: Preparation Of Raw Materialsmentioning

confidence: 99%

Section: Preparation Of Raw Materialsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Preparation and Properties of Phosphate Surfactants Containing Ether and Hydroxy Groups

Osanai

Yamada

Hidano

et al. 2009

J Surfact & Detergents

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show abstract

“…1 Many factors contribute to irritation, including defatting of skin lipids, surfactant binding to skin proteins followed by denaturation, and surfactant permeability in skin. 2 Reducing this potential for irritation is an active field of technology, 3 and a common approach has been to search for milder surfactants. The monosalts of the monoalkyl phosphates (MAPs) with the general structure (where X + is an univalent cation) comprise one such class, as shown by Imokawa and colleagues, 4 who demonstrated that the monosodium salt of n-dodecyl phosphate ester (which is here designated as NaC 12 MAP) was only 1/10 as irritating as sodium dodecyl sulfate.…”

Section: Introductionmentioning

confidence: 99%

“…Surfactants used in household and personal products are frequently in contact with human skin, with a potential for skin irritation or roughness . Many factors contribute to irritation, including defatting of skin lipids, surfactant binding to skin proteins followed by denaturation, and surfactant permeability in skin . Reducing this potential for irritation is an active field of technology, and a common approach has been to search for milder surfactants.…”

Section: Introductionmentioning

confidence: 99%

Quarter-Salt Formation Defining the Anomalous Temperature Dependence of the Aqueous Solubility of Sodium Monododecyl Phosphate

Carnali

Pethica

2006

J. Phys. Chem. B

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The salts of monoalkyl phosphates (MAPs) have been identified as a class of inherently mild surfactants for use in household and personal products. They represent an anionic species intermediate in terms of pKa between the sulfates and the carboxylates and are analogous to the carboxylates in that they form acid-salts (which are here termed quarter-salts)-hydrogen-bonded dimers consisting of an undissociated MAP acid and an MAP monosalt. These complexes precipitate from solutions of the monosalt over a range of lower MAP concentrations giving rise to an unusual solubility/temperature relationship. The solubility of monosodium monododecyl phosphate (NaC(12)MAP) increases with temperature up to 0.01 M at approximately 60 degrees C, which corresponds to the conventional Krafft point as shown by the appearance of micelles in solution. The solubility then increases further to approximately 0.04 M as the solubility temperature declines from 60 to 38 degrees C. The transition between these two trends is characterized by a rather sharp temperature maximum in the solubility curve. In a third stage, the solubility then rises rapidly with very small change of temperature. This unusual overall behavior is shown to correspond with three distinct solid-phase compositions for the precipitates at temperatures below the solubility curve. At the lowest concentrations and up through the Krafft Point, the solid phase has been identified as the stoichiometric quarter-salt. Over the declining temperature portion of the solubility curve, the supernatant solution coexists with a macroscopic mixture of separate quarter-salt and monosalt solids. In the high-concentration third region the solid phase is exclusively the MAP monosalt. The coprecipitation of quarter-salt and monosalt from the monosalt solution occurs reversibly in the declining portion of the solubility curve and is accompanied by an increase in pH. The four phase system (solution, vapor, and two pure solid phases) retains one degree of freedom according to the phase rule since the system is in effect three component in that region.

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Preparation and surface‐ active properties of new amphipathic compounds with two phosphate groups and two long‐ chain alkyl groups

Zhu

Masuyama

Okahara

1991

J Americ Oil Chem Soc

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New compounds bearing two dihydrogen phosphate groups and two long‐ chain alkyl groups (octyl or decyl) were prepared in good yields by the reaction of 1,ω‐bis(alkyloxymethyl)‐ oligo (ethylene glycol)s with polyphosphoric acid.Amphipathic di‐ or tetrasodium phosphates were obtained by neutralization of the free acids with sodium hydroxide, and their surface‐ active properties in water were measured. Almost all these di‐ or tetrasodium phosphates showed good water solubility. Their abilities to form micelles and to lower surface tension were fairly good as compared with general monoalkyl phosphates consisting of one longer alkyl chain and one hydrophilic group. The foaming property of aqueous solutions of the tetrasodium salts was different from that of the disodium salts. The former showed very low foaming ability.

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Study on Skin‐Irritating and Biological Properties of Monoalkyl Phosphate Anionic Surfactants

Cited by 9 publications

References 11 publications

Preparation and Properties of Phosphate Surfactants Containing Ether and Hydroxy Groups

Preparation and Properties of Phosphate Surfactants Containing Ether and Hydroxy Groups

Quarter-Salt Formation Defining the Anomalous Temperature Dependence of the Aqueous Solubility of Sodium Monododecyl Phosphate

Preparation and surface‐ active properties of new amphipathic compounds with two phosphate groups and two long‐ chain alkyl groups

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