Application of anionic phosphorus derivatives of alkyl polyglucosides

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Application of anionic phosphorus derivatives of alkyl polyglucosides for the production of sustainable and mild body wash cosmetics Artur Seweryn, and Tomasz Bujak ACS Sustainable Chem. Eng., Just Accepted Manuscript • DOI: 10.1021/ acssuschemeng.8b04711 • Publication Date (Web): 18 Oct 2018 Downloaded from http://pubs.acs.org on October 23, 2018

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ACS Sustainable Chemistry & Engineering

Application of anionic phosphorus derivatives of alkyl polyglucosides for the production of sustainable and mild body wash cosmetics Artur Seweryn†*, Tomasz Bujak‡ †Department

of Chemistry, Faculty of Material Science, Technology and Design, Kazimierz Pulaski University of

Technology and Humanities, Chrobrego 27, 26-600 Radom, Poland; [email protected] ‡

Faculty of Cosmetics and Pharmaceutical Products Technology, Department of Cosmetology, University of Information Technology and Management in Rzeszow, 2 Sucharskiego Street, Rzeszow 35-225, Poland, [email protected]

*Corresponding Author

Artur Seweryn E-mail: [email protected] Tel. +48 (48) 361 7575 Address: Kazimierz Pulaski University of Technology and Humanities, Faculty of Material Science, Technology and Design, Department of Chemistry, Chrobrego 27, 26-600 Radom, Poland. Abstract This paper explores the possibility of using phosphorus derivatives of alkyl polyglucosides with varying alkyl chain lengths (C4; C8; C10; C12), obtained from natural raw materials, in the production of mild and eco-friendly body wash cosmetics, as examples of sustainable products. The central assumption was that partial replacement of Sodium Laureth Sulfate, which is widely used as the primary washing compound in such products, with this type of anionic surfactants would result in products with improved safety-in-use – in terms of their mild effect on the skin – and more environmentally friendly characteristics. Prototypical products formulated with phosphorus derivatives of alkyl polyglucosides were found to have significantly lower zein number values and produce a smaller increase in the pH of bovine serum albumin solution compared to a reference sample formulated without these compounds. The findings suggest a marked reduction in the skin irritation effect of cosmetics. In addition, the application of this type of anionic surfactants in body wash products significantly decreases their ability to emulsify fats.

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Consequently, as demonstrated in corneometric tests, the skin-drying effect produced by the washing process is significantly reduced.

Synopsis: In this work there were analyzed the possibility of using derivatives of alkyl polyglucosides for the production of mild, ecological and sustainable cosmetics products. Key words: sustainable cosmetics; phosphorus alkyl polyglucosides derivatives; skin irritation; skin drying effect Declarations of interest: The authors declare no competing financial interest.


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INTRODUCTION Sustainable products, as the very name implies, comply with the principles of sustainable development. They result from a production process which has positive environmental effects and thus leads to social and economic benefits. As Belz and Peattie

1

indicate, sustainable

products are goods which meet customer needs and significantly improve societal and environmental well-being during their entire lifecycle in comparison to conventional or competitive product offerings. In their definition of sustainable products, Martin and Schouten

2

point out that such goods do not contribute to elevated concentrations of harmful substances in the ecosphere, do not contaminate the environment with toxic materials, fossil coal or synthetic materials, and do not increase the degradation of ecosystems. As Emery 3 notes, the development of a sustainable product requires, as early as in the phase of design, placing equal importance on the functional and aesthetic features, and safety to humans and the environment. As a consequence, it is necessary to optimize the composition and technology employed for the manufacture of sustainable products, and evaluate their quality. Products designed for cleaning the body represent one of the largest product groups of the cosmetic industry. Appropriate quality parameters in body wash products are achieved by selecting their form as well as quantitative and qualitative composition. In terms of physicochemical properties, body wash products are aqueous solutions of (anionic and amphoteric or nonionic) surfactants and various types of additives including viscosity modifiers, coloring agents, preservatives and active ingredients (e.g. protein hydrolysates, vitamins or plant extracts). 4, 5 Development trends currently observed in the segment of cosmetics formulations fully conform to the requirements associated with the concept of sustainable product manufacturing. They include using natural raw materials in the production process, increasing the degree of product concentration and improving the level of safety both in terms of consumer use and impact on the natural environment.

6, 7

Nowadays there is a growing interest, both among

producers and consumers, in cosmetics formulated with ingredients of natural origin. The tendency is a part of the general market trend toward the promotion of health and environmental protection, which encourages initiatives aimed at reducing the impact of products on people and the environment. Actions taken by manufacturers as well as scientists include industrial research and development efforts related to innovative solutions in the field of cosmetic manufacturing 3 ACS Paragon Plus Environment


technology based on surfactants of plant origin and containing natural ingredients with moisturizing, conditioning and refatting properties, including active ingredients derived from plants (plant extracts). These activities are oriented towards obtaining products characterized by appropriate quality parameters, safe for humans (especially with respect to their impact on the skin), and neutral to the natural environment. 6-13 A sufficiently high level of washing performance in body wash cosmetics is mainly achieved through the use of anionic surfactants.

4, 5, 14

An ingredient widely used in industrial practice is

Sodium Laureth Sulfate (SLES). It has desirable detergent and foaming properties but, more importantly for manufacturers and process engineers, it is a relatively low-priced raw material, and its aqueous solution is easily susceptible to viscosity modifications with electrolytes, mainly with sodium chloride. Despite its numerous advantages, this anionic surfactant is produced by synthesis from raw materials of petrochemical origin and and some studies indicate that it can irritate the skin.

14-18

Faced with increasingly rigorous expectations of users and trends towards

the use of raw materials of natural origin, manufacturers search for anionic surfactants alternative to SLES and capable of replacing this compound as the primary washing ingredient. In the light of the current development trends in the segment of body wash cosmetics which promote the use of natural raw materials, an alternative to anionic surfactants widely used nowadays as the main ingredient in product formulations of this type may be anionic alkyl polyglucoside (APG) derivatives. APGs themselves grow in popularity as a class of chemical compounds used in the production of cosmetics. These nonionic surfactants were produced from renewable raw materials such as vegetable oils, sugar, starch and are a complement to ethoxylates owing to their beneficial human and environmentally friendly properties (high biodegradability, non-toxicity and lack of irritating effect on the skin).

19-24

Since APGs are easily available and

relatively inexpensive to use, there is a growing body of work on methods to obtain APG derivatives that would retain the unique properties of APGs but also eliminate their disadvantages including relatively low water solubility, low stability and tendency to form poorly soluble whitecolored sediments in solutions. Numerous scientific publications in this area discuss the synthesis of APG derivatives containing, among others, sulfosuccinate and phosphate groups which give them the characteristics of anionic surfactants and modify their properties to achieve an even more favorable functional profile, for example as washing compounds in the cosmetics industry (improved detergent and foaming properties). As the literature review shows, studies of anionic 4 ACS Paragon Plus Environment

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derivatives of APGs published to date represent basic research and are mostly limited to describing the synthesis of the compounds and determining their physicochemical properties. 25-31 Only a few and scanty reports, mainly collective papers 32, 33 and patent descriptions 34-36, point to their practical industrial applications, however there is no detailed information on the functional properties of products in which such APG derivatives would be used. This paper presents the results of studies investigating the application of phosphorus derivatives of alkyl polyglucosides with varying alkyl chain lengths (C4, C8, C10 and C12) in the production of body wash formulations exhibiting a mild skin effect. The studies were conducted with commercially available raw materials. As the literature shows, they are anionic surfactants with a gemini-type structure, obtained from APGs, with hydroxypropyl phosphate as a connector 33, 37.

The formulations were developed and four prototypical products were prepared with the

assumption that half of the weight of their primary washing compound would be replaced with an anionic derivative of APG. A formulation based entirely on SLES was used as the reference sample in the study. The prototypical products were analyzed to determine their safety-in-use with respect to skin impact (such as zein number measurements, changes in pH of BSA solution, evaluation of the degree of skin dryness after washing and and the ability to emulsify fatty soiling). MATERIALS AND METHODS Materials The body wash formulations were made using raw materials which are applied for the production of

cosmetics: Sodium Laureth Sulfate (Texapon N70; BASF, Germany),

Cocamidopropyl Betaine (Empigen BS FA; Huntsman, USA), Coco Glucoside (Plantacare 818; BASF, Germany), Coco Glucoside and Glyceryl Oleate (Lamesoft PO65; BASF, Germany), Glycerin (CremerGlyc; Cremer Oleo GmbH & Co. KG, Germany), Sodium Chloride (Sodium Chloride; POCh S.A., Poland), Citric Acid (Citric Acid Monohydrate; POCh S.A., Poland), distilled water. New raw materials that are the subject of this work anionic alkylpolyglucosides derivatives: Sodium Dibutylglucosides Hydroxypropyl Phosphate (SugaPhos 4000; Colonial Chemical Inc., United States), Sodium Didecylglucosides Hydroxypropyl Phosphate (SugaPhos 1000; Colonial Chemical Inc., United States), Sodium Dilaurylglucosides Hydroxypropyl Phosphate (SugaPhos 1200; Colonial Chemical Inc., United States), Sodium Dicocoglucosides Hydroxypropyl Phosphate (SugaPhos 8600; Colonial Chemical Inc., United States), Sodium 5 ACS Paragon Plus Environment


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Benzoate and Potassium Sorbate as preservatives (KEM BS; Akema Fine Chemicals, Italy), distilled water. Methods Determination of Irritant Potential – Zein Volume Irritant potential of the products was measured using zein test. In the surfactants solution zein protein is denatured and then is solubilized in the solution. This process simulates the behavior of surfactants in relation to the skin proteins.

38-40

In the Zein test procedure, 2 g of protein is

solubilized in 40 g solution of washing formulation sample (10% wt.). The study was carried out using the automatic mineralization system Digestor 8 AR and the automatic nitrogen analyzer Kjeltec 8400. The amount of solubilized protein was determined by Kjeldahl analysis, and the result of the Zein number procedure was expressed as mg of solubilized protein (calculated as nitrogen) in 100 mL of sample. The final result was the arithmetic mean of three independent measurements. The test methodology is described in more detail by Nizioł-Łukaszewska et al. 11,

9-

Seweryn et. al. 41 and Wasilewski et al. 42

Determination of Irritant Potential – pH rise Test with Bovine Albumin Serum (BSA) The method developed by Imokawa and Tavss was employed.

43, 44

The test involves

evaluating the degree of protein denaturation by measuring the pH level of the BSA solution in a solution of the washing compound under study. 50 mL of 2% aqueous solution of BSA and 50 mL of 10% solution of the studied body wash cosmetic were prepared. The pH level of both solutions was adjusted to 5.5 (value corresponding to the pH of healthy human skin) with 25% aqueous solution of citric acid. In the next step, both solutions were combined and thoroughly mixed. The mixture thus prepared was set aside for 72 hours, after which the pH value was measured. The greater is the increase, the stronger is the skin irritating effect of a given product. The results are presented as the percentage increase in the pH value in relation to the level adopted for healthy human skin (pH = 5.5) using the formula: (1) where: 6 ACS Paragon Plus Environment

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ZpH – change in pH value, pH0 – value adopted as the pH of healthy human skin, pHr – mean pH value of the BSA solution in the washing compound solution. Three independent assays were performed for each of the studied fluids and the results were averaged. Evaluation of the ability of the investigated liquids to emulsify oily dirt The ability to emulsify fatty soils was evaluated in tests conforming to the PN-C-77003 standard. The test consists in determining the maximum weight of rapeseed oil which can be emulsified by 1 liter of a washing bath containing 1 wt. % of the evaluated formulation. The final result (mean value of three independent measurements) obtained in the test determining the ability of the evaluated formulation to emulsify fatty soils was expressed in grammas of oil per liter of the evaluated formulation at the concentration of 1 wt.%. The test methodology was described by Seweryn et. al. 41 and Wasilewski et al. 45, 46 Evaluation of the degree of skin dryness after washing The methodology used was that described by Wasilewski et al.

42

The skin drying effect

triggered by the analysed samples was evaluated on the basis of a specially designed original methodology. Methodology was designed according to the recommendations of apparatus producer (Courage-Khazaka). The tests were conducted using a Corneometer CM 825 probe from Courage-Khazaka (Köln, Germany) connected to a Cutometer MPA 580 adapter. The test consisted of measuring the hydration of selected skin areas (test field and control field), performing a model washing process in such a way as to ensure that the test field remained in contact with the washing solution (the control field was washed with distilled water), followed by another measurement of skin hydration in the test and control areas after a precisely defined time. Changes in the skin hydration level (expressed as percent) were a basis for determining the skin drying effect of the product under study. It was assumed that the skin drying effect (expressed as percent relative to the baseline) corresponded to the scale of decrease in skin hydration after time t from product application, expressed as percent. The drying effect was calculated by subtracting the percent change in the hydration level of the test area from the percent change in the hydration level of the control area (after the same time period). 7 ACS Paragon Plus Environment


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The skin drying effect (changes in skin hydration after time t from product application) was calculated with the formula below by averaging the results obtained for all testers participating in the study: (2), where: DE – skin drying effect (change in skin hydration), % NK1 – mean skin hydration after time t from model skin washing in the presence of distilled water (control field), [a.u.], NK0 – mean skin hydration in the test area before skin washing in the presence of distilled water (control field), [a.u.], NB1 – mean skin hydration after time t from model skin washing in the presence of the test product (test field), [a.u.], NB0 – mean skin hydration in the test area before model skin washing (test field) [a.u.]. RESULTS AND DISCUSSION Development of formulations and technologies for the production of body washing products The study material consisted of formulations of body wash cosmetics prepared according to previously developed compositions and production technologies, containing a phosphorus APG derivative as the variable ingredient. The compositions of the cosmetics were based on the literature data and own experiences in cosmetic technology.

4, 5, 9-11, 47, 48

The compositions of

prototypical products formulated and prepared for the purpose of the study are listed in Table 1. Table 1 In order to prepare the formulations with the compositions shown in Table 1, individual ingredients (surfactants and additives) were added to water at a temperature of 25°C in the required amounts and appropriate sequence. After adding each ingredient, the solution was mixed with a mechanical stirrer at a speed of 500 rpm for about 20 minutes (time necessary to achieve total dissolution of the raw material). In the final step, the pH of the formulations was adjusted to 5.5 using 25% citric acid solution. The formulations thus prepared were set aside for deaeration. 8 ACS Paragon Plus Environment

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The resulting products were clear and stable after three months of storage in normal conditions, and then subjected to detailed tests. Determination of irritant potential – Zein Value and pH rise Test with Bovine Albumin Serum (BSA) Surfactants, which are among the main ingredients of body wash cosmetics, can affect the surface of the skin, causing cutaneous irritation. Scientific studies in this field show that anionic surfactants in particular may interact with the stratum corneum, causing tissue swelling and elution of water-soluble small molecular components, and inactivating enzymes. The central role in this type of interactions is attributed to the presence of monomers, i.e. individual surfactant molecules, in the washing bath. Through electrostatic interactions with epidermal proteins, monomers can cause changes in their chemical structure and lead to their denaturation. Furthermore, the accumulation of surfactant monomers close to the surface of the epidermis may impair the ordered structure of the cellular cement and result in the elution of its constituent substances such as lipids. These effects result in skin irritation, impairment of the epidermal barrier manifested as a decrease in skin hydration and increase in transepidermal water loss (TEWL), and in extreme cases the development of inflammation. 18, 38, 49, 50 As shown by multiple scientific studies, non-invasive methods of evaluating the skin irritation potential of surfactants as well as finished cosmetic products and household cleaners based on compounds of this type include measurements of zein number and determination of pH changes of the BSA solution. Both methods make use of model proteins exhibiting marked structural similarity to the proteins building the epidermis, and the observed and instrumentally measured interactions with surfactants reflect processes taking place during the contact of this type of compounds with the skin. 38, 51 - 58 The results of zein number measurements performed for prototypical body wash products containing phosphorus derivatives of alkyl polyglucosides are shown in Figure 1. Figure 1 The values of zein number (ZN) obtained for the tested prototypical products vary within a wide range of 32–160 mg N/100 mL. The highest result in the study was recorded in the sample S-0 containing SLES (160 mg N/100 mL) as the only washing compound. A marked decrease in zein number, to values in the range of 32–45 mg N/100 mL, was observed in the samples 9 ACS Paragon Plus Environment


formulated with phosphorus APG derivatives. The type of anionic phosphorus derivative used was not found to have a significant effect on the parameter under study. Data found in the scientific literature show that surfactants or surfactant-based products (such as cosmetics) can be regarded as non-irritant if their ZN does not exceed 200 mg N/ 100 mL48, 52. The ZN values determined in the studied samples (including the SLES-based reference sample) were markedly lower than the values defined for non-irritant products in the literature. This observation may be due to the presence of other types of surfactants (nonionic and amphoteric) in the formulation. According to the literature, such auxiliary surfactants introduced into the solution of anionic surfactants reduce their skin irritation potential through the stabilization of micelles forming in the solution, among other mechanisms.

38, 59

In the present study, the assumption was to replace

the anionic surfactant used as the primary washing compound with more environmentally friendly phosphorus APG derivatives of natural origin. As the results show, partial replacement of SLES, an ingredient with a relatively high irritation potential (producing the highest value in the study), with surfactants of this type makes it possible to obtain cosmetics with ZN values in the minimum range and, therefore, free of any skin irritation potential. The ZN results (Figure 1) obtained were subsequently verified by determining pH changes of the BSA solution. The results are shown in Figure 2. Figure 2 The study results obtained for the analyzed prototypical products corroborate the findings of the zein test. The highest increase in the pH value, by approximately 20%, was noted in the reference sample (S-0). In other cosmetics the incorporation of APG derivatives to partially replace SLES contributes to a significant reduction in the value of the analyzed parameter. With surfactants of this type, the pH increase was only 7–7.5% in relation to the standard value adopted for healthy human skin (pH = 5.5). In order to reduce the skin irritation potential of cosmetic products, a number of methods, based on various mechanisms, are employed to decrease monomers concentration in an aqueous solution. The target mechanisms include an increase in the size of micelles forming in the system and their stabilization, or the formation of appropriate monomer complexes with high molecular weight compounds, which contributes to a decrease in the monomer concentration in the volume phase. Micelles present in aqueous solutions are thermodynamically unstable aggregates 10 ACS Paragon Plus Environment

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exhibiting a tendency to constantly disintegrate with the release of monomers into the volume phase of the solution. The application of various types of surfactants into the systems induces a significant reduction in the amount of released monomers and, consequently, improves the stability of micellar aggregates. Such effects can also be achieved by incorporating different types of surfactants 60, polymers or biopolymers 48, 49, hydrophobic and refatting substances 42, 61, 62

or plant extracts

9, 11,

into product compositions. In the present study, the addition of anionic

surfactants of a different type to the body wash cosmetics is likely to lead to the formation of much larger and more stable mixed micelles in the aqueous solution, which in turn causes a decline in the amount of free surfactant monomers in the solution. Gemini-type APG derivatives, which are composed of relatively big particles, form large-sized micelles characterized by limited ability to penetrate into the epidermis and reduced likelihood of interactions with proteins. This results in a decrease in the irritant effect of the formulations, as shown in the studies (Figure 1 and 2). A similar effect was observed by Klimaszewska et al. 60, who showed in their study that partial replacement of SLES with a different type of anionic surfactant in body wash cosmetics for children triggered a significant decrease in the skin irritation effect associated with the formulations. Based on the analysis of particle size distribution, the researchers indicate that this effect is achieved owing to the formation of much larger and more stable mixed micelles – built by surfactants with different values of the hydrophilic-lipophilic balance (HLB) constant – in the aqueous solution. Another significant factor is the chemical structure of anionic surfactants added to the formulation as the primary washing compound. Surfactant-protein interactions involve the interplay between hydrophobic fragments of hydrocarbon chains and hydrophobic protein fragments, and electrostatic effects between the charged polar surfactant heads and some charged parts of the protein. Consequently, ionic surfactants with a reduced number and length of the hydrocarbon chain and a decreased charge density of the hydrophilic part will be characterized by a limited irritant effect, for example through the introduction of an additional hydrophilic part in the form of ethylene oxide groups. A very important process initiating changes in the structure of proteins due to the presence of surfactants is the adsorption of these compounds on the protein. In surfactants with large main functional groups their size is reduced, resulting in weak interactions with the protein.

35, 60-62

The above assumptions were confirmed in the present study, in tests

analyzing the irritant effect of the prototypical products. The studied APG derivatives contain a 11 ACS Paragon Plus Environment


phosphate group as the hydrophilic part. Compared to the sulfate group in Sodium Laureth Sulfate, it is larger in size and has a lower charge density. In addition, the hydroxyl groups contributed by APGs in the proposed compounds increase the hydrophilicity of the surfactant. Consequently, unlike Sodium Laureth Sulfate, compounds of this type may have a limited effect on proteins, and their incorporation into a cosmetic product may contribute significantly to reducing the skin irritation effect of the formulation, as demonstrated in the studies Evaluation of ability to emulsify fatty soils The washing mechanism comprises a number of processes aimed at removing, among others, environmental soiling and cutaneous secretions (e.g. sweat and sebum) from the skin surface. A key constituent process during skin washing is the emulsification of soiling in the washing bath solution. It ensures permanent and effective removal of contaminants from the skin surface, helping to maintain an appropriately high level of hygiene. On the other hand, a cosmetic with an excessive ability to emulsify fatty soils may lead to an undesirably high degree of removal of protective epidermal lipids which are responsible for maintaining an appropriate level of epidermal hydration and provide a protective barrier against the penetration of environmental pollutants and pathogens into the deeper layers of the skin Other potential effects include the disruption of the intercellular cement structure in the stratum corneum and solubilization of its constituent lipids. These processes may damage the enzymes producing lipids in the intercellular matrix, trigger an increase in TEWL, cause the sensation of dry skin and cracking and, in extreme cases, lead to erythema and disruption of epidermal exfoliation processes. 38, 49, 59, 68 Another vital aspect from the viewpoint of healthy skin is the possibility of uncontrolled removal of naturally occurring bacterial flora from the skin surface due to excessive detergent properties of cosmetic products. This is manifested by a change in the pH value of the skin, which may lead to cutaneous dysfunction. 38, 69-72 The results of tests determining the ability of prototypical products containing various types of phosphorus APG derivatives to emulsify fatty soils are presented in Figure 3. Figure 3 The values of the evaluated parameter in the prototypical body wash cosmetics under study were found to be in the range of 15–25 g/L. The highest test results were obtained for the 12 ACS Paragon Plus Environment

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reference sample (S-0) and for the product containing a phosphorus APG derivative with an alkyl chain length of C12. The determined value of the ability to emulsify fat soils in these formulations is relatively high, amounting to 25 g/L. In the remaining prototypical products the values of the study parameter were equal to 15–20 g/L. These findings are consistent with the literature data demonstrating the highest detergent ability in surfactants with a hydrocarbon chain length of C12. The value of the HLB constant in these substances ensures their optimal activity as washing and emulsifying compounds. 66, 67 The purpose of body wash cosmetics is to remove dirt from the skin surface. As a result, products of this type do not require an excessive ability to emulsify fatty soils, since such contaminants are not particularly stubborn or difficult to remove. The composition of such products should be optimized so that, on the one hand, they provide good washing performance and, on the other, do not cause excessive lipid extraction from the skin. The assumption of the present study was that the application of phosphorous APG derivatives as the main washing compound would result in the formulation of skin-friendly cosmetic products. A decline in the evaluated parameter is noted in the majority of the prototypical products under analysis (except for S-3), which seems beneficial with respect to product impact on the skin. A lower ability to emulsify fats may lead to decreased lipid elution from the skin in the washing process, thus improving product safety in terms of its effect on the skin. Similar conclusions were reached by Ananthapadmanabhan et al.

73, 74,

who, in their studies, evaluated the ability of model surfactant

solutions to solubilize stearic acid. Based on their findings, the researchers claim that reducing the solubilization ability of the compounds increases their safety in terms of a mild effect on the skin, by decreasing the elution of hydrophobic components naturally present in the epidermis. Evaluation of skin condition after the washing process Body wash cosmetics are formulated in such a manner as to achieve an appropriate level of washing performance in the finished products. Especially anionic and nonionic surfactants are highly effective at reducing interfacial tension and producing an emulsifying effect.

14, 67

The

washing process may involve excessive removal of hydrophobic components (contaminants and skin lipids) from the skin, resulting in the depletion of naturally occurring valuable fatty components. Damage to the natural skin barrier intensifies TEWL, which is followed by 13 ACS Paragon Plus Environment


significant drying of the skin. The assessment of the ability of the prototypical products to emulsify fatty soils showed that the use of phosphorus APG derivatives contributed to the deterioration of these properties (Figure 3). What is important, though, is whether lowering this parameter in the prototypical products has an influence on the condition of the skin after the washing process. To this end, corneometric tests were carried out, with results shown in Figure 4. Figure 4 All the cosmetics tested exert a drying effect (DE) on the skin. The highest values (35 and 27% after 1 and 3 hours of testing, respectively) were noted for the reference sample (S-0) and the sample containing a phosphorus APG derivative with an alkyl chain length of C12 (S-3). The application of other APG derivatives has a significant effect on lowering the value of the parameter determined in corneometric tests. They were associated with a reduction in skin drying by approximately 8–10% in relation to the baseline formulation. The study results show an equivalent effect to the ability to emulsify fatty soils determined for the cosmetics (Figure 3). A partial replacement of Sodium Laureth Sulfate, a commonly used washing compound, with phosphorus APG derivatives results in a decrease in the detergent properties of the resulting products. As a consequence, damage to the epidermal barrier preventing water evaporation from the skin is reduced, which has an effect on the results of skin drying obtained in studies. CONCLUSIONS The study examined the possibility of producing skin-friendly body wash cosmetics by using anionic phosphorus derivatives of alkyl polyglucosides obtained from raw materials of natural origin as the primary washing compound. It was shown that partial replacement of Sodium Laureth Sulfate, which is widely used as the primary washing compound, with APG derivatives is a method of obtaining products with improved safety-in-use with respect to their mild effect on the skin. The zein test and the evaluation of pH changes of the BSA solution, performed to assess the irritant effect of the products, revealed significant declines in values obtained for the formulated prototypical products, as compared to the reference sample. In addition, the compounds used were not found to significantly affect the determined parameters. The incorporation of phosphorus APG derivatives with carbohydrate chain lengths of C4, C8 and C10 14 ACS Paragon Plus Environment

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impaired the ability of the formulations to emulsify fatty soils. As demonstrated in the assessment of the degree of skin dryness after the application of cosmetics, this decreases the intensity of their impact on the skin and contributes to a reduced skin drying effect of the products. The results of the study indicate that despite their anionic character phosphorous APG derivatives are an alternative to commonly used surfactants of this type, and can be employed as washing compounds offering an increased level of safety in terms of interactions with the skin. Acknowledgements Funded with the assistance of the Ministry of Science and Higher Education from subsidies for statutory activity. Project no. 3086/35/P entitled “Development of formulations and technologies for the manufacture of innovative cosmetics, pharmacy supplies, household and industrial chemicals”. References (1) Peattie, K.; Belz, F.M. Sustainability marketing – An innovative conception of marketing. Marketing Review St. Gallen 2010, 27(5), 8 – 15. DOI: 10.1007/s11621-010-0085-7 (2) Martin, D.; Schouten, J. Sustainable Marketing; Prentice Hall: New York, 2012, pp. 124-128. (3) Emery, B. Sustainable Marketing; Pearson Education Limited: Edinburgh, 2012, pp. 161 – 180. (4) Barel, A.; Paye, M.; Maibach, H. I. Handbook of Cosmetic Science and Technology, Third Edition; CRC Press: New York, 2009. (5) Butler, H. Poucher’s perfumes, cosmetics and soaps, Springer Science & Business Media, Kluwer Academic Publishers: Dordrecht, 2000. DOI: 10.1007/978-94-017-2734-1 (6) Philippe, M.; Didillon, B.; Gilbert, L. Industrial commitment to green and sustainable chemistry: using renewable materials & developing eco-friendly processes and ingredients in cosmetics. Green Chem. 2012, 14(4), 952 – 956. DOI: 10.1039/C2GC16341A (7) Jenck, J. F.; Agterberg, F.; Droescher, M. J. Products and processes for a sustainable chemical industry: a review of achievements and prospects. Green Chem. 2004, 6(11), 544 – 556. DOI: 10.1039/B406854H (8) Dimitrova, V.; Kaneva, M.; Gallucci, T. Customer knowledge management in the natural cosmetics

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Table 1. Model formulations of body cleansing cosmetics Ingriedents (INCI*) Sodium Laureth Sulfate Sodium Dibutyl Glycosides Hydroxypropyl Phosphate Sodium Didecyl Glycosides Hydroxypropyl Phosphate Sodium Dilauryl Glycosides Hydroxypropyl Phosphate Sodium Dicoco Glycosides Hydroxypropyl Phosphate Cocamidopropyl Betaine Coco- Gluoside Glycerin Coco-Glucoside (and) Glyceryl Oleate Sodium Chloride Sodium Benzoate and Potassium Sorbate Citric Acid Aqua

Concentration [wt. %] S-2 S-3 4.0 4.0

S-0 8.0

S-1 4.0

S-4 4.0

-

4.0

-

-

-

-

-

4.0

-

-

-

-

-

4.0 4.0

1.0 2.0 2.0 0.5 1.0 0.5 to pH 5.5 ad 100

*INCI (International Nomenclature of Cosmetic Ingredients)



Figure captions Figure 1 Zein values determined for 10% aqueous solutions of body cleansing cosmetics containing different phosphorus alkyl polyglucosides derivates types. Figure 2 Changes in pH of the mixture of Bovine Serum Albumin solutions (BSA) and body cleansing cosmetics containing different phosphorus alkyl polyglucosides derivates types. Figure 3 Ability to emulsify fatty soils determined for body cleansing cosmetics containing different phosphorus alkyl polyglucosides derivates types. Figure 4 Drying effect of body cleansing cosmetics containing different phosphorus alkyl polyglucosides derivates types.


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For Table of Contents Only



Figure 1 Zein values determined for 10% aqueous solutions of body cleansing cosmetics containing different phosphorus alkyl polyglucosides derivates types. 127x65mm (600 x 600 DPI)

ACS Paragon Plus Environment

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Figure 2 Changes in pH of the mixture of bovine serum albumin solutions (BSA) and body cleansing cosmetics containing different phosphorus alkyl polyglucosides derivates types. 65x33mm (600 x 600 DPI)



Figure 3 Ability to emulsify fatty soils determined for body cleansing cosmetics containing different phosphorus alkyl polyglucosides derivates types. 63x32mm (600 x 600 DPI)


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Figure 4 Drying effect of body cleansing cosmetics containing different phosphorus alkyl polyglucosides derivates types. 63x31mm (600 x 600 DPI)


Application of anionic phosphorus derivatives of alkyl polyglucosides

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