WO2015200812A1

WO2015200812A1 - Derivatives of esters

Info

Publication number: WO2015200812A1
Application number: PCT/US2015/038020
Authority: WO
Inventors: Christine FOUTS; Anna Pavlovic; Soraya Rohde; Jordan Quinn
Original assignee: Vantage Specialty Chemicals, Inc.
Priority date: 2014-06-26
Filing date: 2015-06-26
Publication date: 2015-12-30

Abstract

Provided are products containing fatty alcohols and methods for making such products. In particular, the products containing fatty alcohols may be used in the making of formulations for use in personal care.

Description

DERIVATIVES OF ESTERS

CROSS-REFERENCE TO RELATED APPLICATION

This application claims benefit of U.S. Provisional Application Number

62/017,825, filed June 26, 2014.

FIELD OF THE INVENTION

In certain aspects, the present invention relates to products that are derived from a class of esters formed from fatty alcohols and fatty acids, including, for example, esters which are produced by plants. In this regard, aspects of the present invention involve the use of "green chemistry" in that products of the present invention are capable of being made from a renewable source of raw material.

BACKGROUND OF THE INVENTION

Jojoba oil contains a mixture of wax esters which vary structurally depending on the length of the carbon chains of the fatty alcohols and of the fatty acids from which the esters are formed. For example, the chain length of each of the alcohols and acids comprising the esters can vary from about 14 carbon atoms to about 26 carbon atoms. There is set forth below a sample structural diagram of the ester.

The source of jojoba oil is the jojoba plant which contains seeds in which the liquid oil is produced. Examples of geographical areas in which the plant is grown include the U.S., Mexico, Israel, Australia, South Africa and other nations of Africa, and various parts of Latin America. The lands on which the jojoba plant is grown are typically semi-arid.

BRIEF SUMMARY OF THE INVENTION

In one aspect, the present invention provides a product prepared by reacting a starting material comprising: (A) at least one ester comprising the residue of a fatty alcohol and the residue of a fatty acid in which each of the fatty alcohol and the fatty acid is monounsaturated and the carbon chain length of each of the fatty alcohol and the fatty acid is about 14 to about 26 carbon atoms, and the chain thereof is straight; with (B) at least one reactant which converts the ester to a mixture of (i) the fatty alcohols of said ester and (ii) a salt of the fatty acid of said ester; and separating from the mixture said fatty alcohols. In another aspect, the present invention provides a method of preparing a product comprising at least one fatty alcohol comprising the steps of: a) combining jojoba oil, which comprises waxy esters that comprise the residues of fatty alcohols and the residues of a fatty acids, with NaOH or KOH solution in the presence of a solvent to form a reaction mixture; b) heating the reaction mixture until the oil is completely saponified to produce (i) the fatty alcohols of said esters and (ii) salt of the fatty acids of said esters; and c) filtering the saponified reaction mixture to separate therefrom a liquid comprising the fatty alcohols.

In another aspect, the present invention provides an emulsion comprising at least one fatty alcohol.

In a further aspect, the present invention provides a personal care formulation comprising at least one fatty alcohol.

BRIEF DESCRIPTION OF THE DRAWINGS

Figure 1 shows gas chromatography demonstrating the purity of jojoba alcohol and jojoba acid derived from potassium jojobate as >90% each.

Figure 2A-2D shows emulsions containing jojoba derivatives as viewed under a microscope at 400x enlargement. A) Emulsion containing jojoba alcohol. B) Control formula emulsion. C) Emulsion containing potassium jojobate. D) Emulsion containing jojoba Illuminate.

Figure 3 shows emulsions containing jojoba derivatives produced according to the formulae of Table 3. Figure 4 shows effects of a test cream containing jojoba alcohol on visible wrinkles in volunteers.

Figure 5 shows a comparison between the time observed for skin absorption for control cream compared to the time observed after administration of the cream with jojoba alcohol added.

DETAILED DESCRIPTION OF THE INVENTION

According to embodiments of the present invention, products are derived from an ester (hereafter referred to also as "the ester") comprising the residue of a monounsaturated fatty alcohol and the residue of a monounsaturated fatty acid. Although the ester can be synthesized by reacting a suitable fatty alcohol and fatty acid, it is preferred that a natural source of the ester be used in preparing the products. The preferred natural source of the ester is jojoba oil which itself comprises the ester

(referred to also as a "wax ester") of a straight chain, monounsaturated fatty alcohol and a straight chain, monounsaturated fatty acid.

In preferred form, a product according to an embodiment of the present invention is prepared by utilizing "green chemistry". This involves the use of refined jojoba oil which includes at least about 98 wt.% of a waxy ester which comprises the residue of a fatty alcohol and the residue of a fatty acid, each of the fatty alcohol and the fatty acid being monounsaturated and the carbon chain length of each of the fatty alcohol and the fatty acid being about 14 to about 26 carbon atoms. The refined jojoba oil is combined with a reactant(s) which forms a mixture comprising (i) the fatty alcohol of said ester and (ii) a salt of the fatty acid of said ester. Each of the fatty alcohol and salt of the fatty acid can be separated from the mixture and used in various applications as described below.

There are numerous advantages that flow from the use of jojoba oil as a starting material for use in the practice of aspects of the present invention and of products that are derived from jojoba oil. For example, jojoba oil is derived from the jojoba plant which thrives in a semi-arid desert environment where other plants would not survive. The lands on which the plant is grown do not require irrigation and do not compete for land needed to grow crops which are considered to be essential. There are known economic methods for extracting the jojoba oil from the plant, including refined jojoba oil. Compared to other oils derived from renewable sources, jojoba oil and products derived therefrom are relatively stable under a variety of conditions and the oil and products do not contain triglycerides that are a source of glycerin which can affect adversely applications in which triglycerides and glycerin are used, and accordingly, their use is undesired. Products made therefrom are considered safe and do not cause irritation when applied to the skin. Other advantages associated with aspects of the present invention are described below.

The jojoba oil used as the starting material is mechanically squeezed from the nut of the jojoba fruit. In embodiments, this oil is filtered through natural clay, to produce clear jojoba oil.

In embodiments, clear jojoba oil is treated with NaOH or KOH solution in a solvent, specifically ethanol or isopropanol or other suitable alcohol or glycol, and fully saponified. After saponification is completed, the soap is filtered off from the jojoba alcohol solution. The solvent is distilled off and the final product is filtered through a filtrate aid. This final product may be used as such in various personal care

applications, as described herein.

Exemplary of an ester mixture present in a jojoba oil is one in which at least about 50 wt.% of the mixture comprises esters in which the length of each of the fatty alcohol and fatty acid chains comprises 18, 20, 22, 24, and 26 carbon atoms.

Common to the esters comprising jojoba oil is that each of the fatty alcohols and fatty acids from which the ester is formed possesses one site of unsaturation, that is, each of the alcohol and acid is monounsaturated. The site of unsaturation is potentially functional in that it can serve as a reactive site for preparing various derivatives by participating in reactions such as, for example, oxidation, oxidative cleavage of the double bond, and olefin metathesis.

Speaking generally, jojoba seed contains about 50 wt.% liquid of which about 85 wt.% of the liquid comprises the wax esters described herein. This is a general statement in that the particular amount of the liquid wax esters contained within the jojoba seed and the particular composition of the wax esters will tend to vary depending on the particular jojoba plant which is the source of the wax esters and the geographical area where the plant is grown. There can be slight differences between batches of the oil in the form of the ester wax distribution due to location and weather conditions, but on the average, jojoba oil (jojoba wax esters) are similar within a small range across all regions where the jojoba plant is being harvested. Properties of the products according to embodiments of the present invention are not adversely affected by virtue of the variations of the plant or growth area thereof.

The balance of jojoba seed is the jojoba seed meal (solids) which are referred to herein as the "residue." In embodiments of the present invention, the liquid wax esters described herein can be separated according to known procedures from the residue to provide a liquid composition of jojoba oil in which the wax esters comprise at least about 98 wt.%, typically about 98 to about 100 wt.% of the wax esters. The liquid wax esters which are separated from the residue are referred to hereafter as "refined jojoba oil", which may be saponified as described below.

The saponification produces a mixture of jojoba alcohols of the present invention and a salt of the fatty acid derived from the ester described above.

The refined jojoba oil can be saponified using potassium hydroxide or sodium hydroxide dissolved in a suitable solvent, including a green solvent. Examples of solvents that may be used include, but are not limited to, methanol, ethanol, propanol, isopropanol, ethylene glycol, 1 ,2-propylene glycol, 1 ,2-butylene glycol, 1 ,3-butylene glycol, 1 ,4-butylene glycol, and other glycols or higher order alcohols that are suitable as leave-in solvent. In accordance with known procedures, the refined jojoba oil is combined with the aforementioned solution while stirring the reaction mixture which can be heated, for example, to a temperature no greater than about 75°C. In certain embodiments, the reaction mixture may be heated at a temperature from about 70°C to about 160° C. GC analysis can be used to determine when the reaction is complete. The reaction is typically completed within, for example, about 2 to about 6 hours.

Compounds which are produced by the reaction, which include jojoba alcohols and the salts of the fatty acids, can be transferred to a vessel where they are allowed to separate into phases. In accordance with the present invention, liquid jojoba alcohols can be separated and recovered from the solid salt of the fatty acid utilizing filtration, washing of the solid salt with one of the aforementioned solvents and then removing the solvent by vacuum distillation.

In accordance with aspects of the present invention, there is provided a product prepared by reacting: (A) at least one which comprises the residue of a fatty alcohol and the residue of a fatty acid in which each of the fatty alcohol and the fatty acid is mono- unsaturated, has a straight chain and a chain length of about 14 to about 26 carbon atoms; with (B) a reactant(s) which forms a mixture comprising the fatty alcohol of said ester and a salt of the fatty acid of said ester. In accordance with the present invention; the fatty alcohol(s) and salt(s) of the fatty acid can each be recovered from the mixture separately and used in various applications, for example, personal care applications, as described below.

In embodiments, the saponification process produces a product comprising at least one cis-omega-9 unsaturated fatty alcohol having a carbon chain comprising a number of carbon atoms selected from the group consisting of 18, 20, 22, 24, 26.

In embodiments, the jojoba alcohol produced through the saponification process described herein results in relatively pure (minimum 95%) mixture of cis-omega-9 unsaturated fatty alcohols with carbon chain distribution consisting of C18, C20, C22, C24, and C26 fatty alcohols termed as "jojoba alcohol". These products are generally free of any contaminations that result from chemical transformations when subjected to other chemical processes, such as hydrogenation and hydrogen reduction processes; they are substantially free of trans-alcohols, saturated alcohols and short chain alcohols that can be produced from hydrogenation and reduction of the jojoba acid to jojoba alcohol.

In embodiments, the jojoba alcohol product is substantially free of any alcohols produced by reduction of the acid functionality to alcohol functionality. In embodiments, the product is also substantially free of any alcohols with carbon chain shorter than C18; that is, it is substantially free of C16 and C14 alcohols.

In embodiments, the saponification process fully preserves in its original form the natural cis-geometry around the omega-9 double bond in the saponification products and therefore the jojoba alcohol product, which is a mixture of alcohols of different chain length is substantially free of any contamination with alcohols having trans-geometry around the omega-9 double bond which can be produced during other processes, such as during the hydrogenation of the jojoba oil process. For convenience, the

aforementioned mixture of jojoba alcohols is referred to herein also as "the select alcohol mix".

There is set forth below a preferred composition of the present invention. The composition comprises a liquid mixture of fatty alcohols formed by saponifying jojoba oil; it comprises;

a) 0 to about 6 wt.% of oleic alcohol;

b) about 35 to about 50 wt.% of Cis-1 1 -eicosenol;

c) about 35 to about 50 wt.% of Cis-13-docosenol; d) about 5 to about 16 wt.% of Cis-15-tetracosenol; and

e) 0 to about 6 wt.% of Cis-17-hexacosenol.

Another preferred composition is one in which the amount of each of oleic acid and of C-17-hexacosenol is no greater than about 2 wt.%.

Both the jojoba alcohols and metal salts of the jojoba acids may be suitable for use in personal care applications as separate products or in a mixture of products.

It is believed that the select alcohol mix of the present invention will be used most widely in personal care formulations which, as known, comprise countless compositions that vary in form, function, and the ingredients which comprise the composition.

Examples of such compositions include, but are not limited to, those which exist in the form of lotions, sprays, solid creams, gels, ointments, and serums. Examples of functions which are performed by personal care formulations include, without limitation, the treatment: of lips, for example, lip balms and lipsticks; of hair, for example, shampoos, rinse-off and leave-in conditioners, styling gels, products to protect or repair hair strands, masks, and colorants; of skin, for example, hand creams for conditioning dry and damaged skin, soap cleaning compositions, sanitizers, body scrubs, face lotions; odorants, for example, carriers for colognes, perfumes, and deodorants; and hydration enhancers; of men's skin and hair, for example, shaving creams or gels, after shave balms and facial washes, and facial cleansers; and ofmiscellaneous body parts, for example, nails.

It should be appreciated that various of the personal care formulations disclosed above include cosmetics. The U.S. Food and Drug Administration (FDA) which regulates cosmetics in the United States essentially defines cosmetics as: intended to be applied to the human body for cleansing, beautifying, promoting attractiveness, or altering the appearance without affecting the body's structure or functions. This broad definition includes, as well, any material intended for use as a component of a cosmetic product, but not soap.

It should be appreciated that the particular materials and amounts thereof comprising personal care formulations vary to a great extent depending on the purpose (function) for which the formulation is to be used. Speaking generally the following are examples of ingredients, including classes of ingredients, that are apt to be constituents of formulations used for personal care applications: water; esters of various types, for example, those which are present in vegetable, animal, and mineral sources, and includes, for example, waxes and oils; soaps, for example, sodium and potassium soaps of fatty acids, emulsifiers; surfactants, including, for example, anionic, cationic, and nonionic surfactants; stabilizers, including anti-oxidants; thickening agents;

moisturizers; dyes and pigments as colorants; fillers; solvents including non-aqueous (organic) solvents. In embodiments, suitable oils may include natural vegetable oils including, but not limited to, olive, argan, borage, almond, camelina, castore, grape seed, rose hip, sesame, pumpkin, poppy seed, andiroba, walnut, sunflower, Neem tree, tea tree, and avocado.

Products according to aspects of the present invention can be used in a variety of applications. An exemplary use of the products includes the preparation of emulsions that may be used in a variety of personal care products, including but not limited to, low viscosity lotions and sprays, as well as high viscosity creams and gels. Products according to aspects of the invention may be used in, without limitation, methods of increasing the skin absorption of a composition, methods of improving the skin hydration properties of a composition, methods of preparing compositions that reduce inflammation, methods of preparing compositions that promote anti-aging, methods of preparing compositions that reduce redness, and methods of increasing the

antimicrobial action of a composition.

Products according to aspects of the invention can be used in, without limitation, massage oil that does not contain water phase, in butters and butter creams used for conditioning dry and damaged skin; additionally, products can be added to over-the counter (OTC) compositions such as variety of ointments.

There follows a description of the use of products according to aspects of the present invention in forming emulsions, including, for example, emulsions having improved stability and other desirable properties. In various embodiments, emulsions may include oil-in-water emulsions and water-in-oil emulsions. Oil-in-water (o/w) emulsions comprise a continuous aqueous phase which contain dispersed therein droplets of a liquid which is typically immiscible with water, for example, various types of oil. In order to improve the stability of an emulsion, that is, to prevent or deter premature phase separation of the dispersed liquid droplets, it is well known to form the emulsion utilizing an emulsifying agent, that is, an emulsifier. Products according to aspects of the present invention have emulsifying properties, as illustrated below. The amount of the select alcohol mix used in forming an emulsion can vary, depending on the use of other particular emulsifying agents and the nature of the emulsion, that is, the constituents comprising the emulsion. The emulsifying agent should be used in an amount at least sufficient to form an emulsion that is stable for at least about two months. In embodiments, the amount of the select alcohol mix used in the preparation of an emulsion may be within the range of about 0.01 to about 10 wt% based on the total weight of the ingredients comprising the emulsion. It is believed that amounts within the range of about 0.1 to about 50 wt.% of the emulsifying agent will produce emulsions which have satisfactory stability; nevertheless, it should be understood that higher amounts can be used as needed.

Emulsions prepared according to aspects of the invention may optionally include any suitable cosmetic ingredients both active and inactive, such as mono-, di-, tri- esters of glycerin, natural triglyceride oils, essential oils and other plant extracts, including, but not limited to, water-based and oil-based phytochemical extracts that positively affect skin, hair, and nails treated with the resulting formulae. Emulsions prepared according to aspects of the invention may optionally be prepared in the presence of natural or synthetic polymers. EXAMPLES

The Examples below describe the preparation of compositions of the present invention and comparative test results involving the use of such compositions and of other compositions.

EXAMPLE 1

Preparation of jojoba alcohols of the present invention

A 5 liter round bottom flask was charged with 1230 g of colorless jojoba oil (Vantage Specialty Chemicals); saponification value = 92 mg KOH/g), 1230 g of isopropyl alcohol, and 137.8 g of potassium hydroxide (85%) under nitrogen. The mixture was heated to 80 °C with agitation from an overhead stirrer. The mixture was heated at 80° C for 2 hours, then cooled to 24° C. The resulting suspension was filtered using a Buchner funnel. The filter cake was washed with 3 x 100 ml_ of isopropyl alcohol. The filter cake was dried in air to give 738 g of potassium jojobate as a white solid. The filtrate which contained the liquid mixture of the jojoba alcohols of the present invention was concentrated under vacuum and then gravity filtered to remove residual solids from the liquid mixture. The resulting jojoba alcohols weighed 545 g and consisted of a pale yellow liquid. Gas chromatography confirmed the purity of jojoba alcohols and potassium jojobate as >90% each (Figure 1 ). The pH of jojoba alcohols (2 wt.% in 1 :1 water: isopropyl alcohol) was adjusted from 12.5 to 8.5 by addition of 0.25 N hydrochloric acid in isopropyl alcohol and then concentrated under vacuum.

Table 1 below identifies the mixture of jojoba alcohols (the select alcohol mix) and the proportions thereof that were produced by the reaction described in Example 1 . Table 1

EXAMPLE 1 -A

Table 1 -A below describes another mixture of jojoba alcohols and the proportions thereof that were separated from a mixture of jojoba alcohols and sodium jojobate that was formed by a saponification in which sodium hydroxide was used as the catalyst.

Table 1 -A

COMPARATIVE EXAMPLE 1

Preparation of Potassium Illuminate

Jojoba Illuminate™, which is a hydrolyzed jojoba oil reacted with potassium hydroxide in 1 ,3-propanediol, is prepared according to the following steps.

1 ) Assemble the reaction vessel with an efficient mechanical stirrer and nitrogen sparging during premix preparation and sweeping during hydrolysis step.

Premix:

2) When the vessel is ready, place 1 ,3-propanediol in the vessel and begin stirring, with moderate nitrogen sparging. Begin the addition of KOH. Add KOH slowly while stirring the mixture vigorously to not allow for excessive temperature increase in the vessel. Have a cooling system standing by ready in case the temperature in the vessel begin to rise too quickly. The temperature should not exceed 75° C (170 F) at any point during the premix process. Stir the mixture well throughout the duration of the process of dissolving KOH in 1 ,3-propanediol, with moderate nitrogen sparging. If temperature exceeds 80° C (175 F) for a prolonged time during this process, 1 ,3-propanediol may burn, which may affect the color of the finished product.

Main Reaction:

3) When the temperature of the premix is stabilized at about 70° C (about 160 F), turn on the heating of the reaction vessel for the beginning of this process.

4) Add jojoba oil to the premix as fast as the system allows. Continue vigorous and efficient stirring and nitrogen sparging of the mixture during jojoba oil addition. After the oil is added, switch to nitrogen sweeping throughout the entire reaction time.

5) Obtain sample and test saponification value. Continue reaction until the

saponification value reaches the specifications of <7% (preferably from 0-5%). 6) When the required saponification value has been met, test color (Gardner). If color is greater than 2, add 0.1 % (w/w) of hydrogen peroxide in water. Continue agitation of the product.

When reaction is complete, discontinue heat and place this product in designated containers. Filter the product before putting it into container if needed.

A laboratory batch made through this process produced a snow-white product for which no bleaching was needed.

EXAMPLE 2

Preparation of oil-in-water emulsion

Before beginning the preparation, all the used equipment should be weighed (beakers and stirrers).

Oil phase: Combine all the oil phase components in a pre-weighed beaker and begin heating while efficiently stirring with an overhead mechanical stirrer. The temperature should be set to maximum 70° C and should not be exceeded by more than 5 C°. Keep stirring the oil phase until all components are fully melted and well mixed into a homogeneous mixture.

Water phase: Weigh water, add the preservative to the water first and stir it efficiently while heating to a maximum temperature not exceeding 70° C. When the preservative is dissolved, add the remaining components of the water phase. If thickeners such as Xathan gum are used, make sure that the thickener is evenly dispersed in the volume of the water phase.

When both phases are ready, slowly add the oil phase into water phase while efficiently stirring the water phase. After addition is completed, stir for additional 15-20 minutes at 70° C. After 20 minutes, start cooling the emulsion to room temperature slowly while efficiently stirring. When the temperature of the emulsion reaches 50° C, weigh the entire system and adjust for water lost during the process; add water adjustment drop-wise while stirring. Continue stirring until the emulsion reaches 30° C- room temperature. The emulsion is in the form of a white-milk-like product that can be sprayed easily. Transfer the emulsion into a storage container.

EXAMPLE 3

Effects of jojoba oil derivatives on oil-in-water emulsions

To demonstrate emulsifying properties of jojoba oil and its derivatives, a difficult to stabilize formula was designed. The oil phase of the control contained 50 wt.% of a natural oil mixture made of equal quantities of randomly chosen triglycerides (Argania Spinosa kernel oil, Macadamia seed oil, Grapeseed oil) and jojoba ester liquid wax. Table 2 shows the formulae for emulsions containing jojoba derivatives, including the mixture of jojobal alcohols produced according to Example 1 hereof, (referred to as "jojoba alcohol" in Table 2). All emulsions identified in Table 2 were prepared following a standard oil-in-water formulation technique as described herein above and were stirred with an overhead stirrer at 550 rpm; no homogenization was applied to any of the samples. The products were analyzed under a microscope at 400x enlargement (Figure 2).

Figure 3 identifies the emulsions produced according to the formulae of Table 2. The most unstable emulsion was the "Control" that contained only jojoba oil. The stability of the emulsions and oil droplets dispersion in water improved with addition of jojoba derivatives. Of the three derivatives of jojoba oil, the potassium salt, the

Illuminate (a combination of jojoba salt and jojoba alcohols) and the jojoba alcohols, the jojoba alcohols proved to be superior in generating stable o/w formulae.

The jojoba alcohols of the present invention are also compatible in the more viscous emulsions employing a thickener such as Xanthan gum, as identified in Table 2. The emulsions were prepared both with and without the Xanthan gum that proved to be compatible with all jojoba derivatives (not shown), but the presence of the gum in the formula did not influence the oil phase dispersion in the water phase. The improvement of oil phase dispersion in water was primarily associated with the presence of jojoba alcohols of the present invention. The jojoba alcohols were compatible with all formula components, both hydrophilic and lipophilic.

Table 2

EXAMPLE 4

Effects of jojoba alcohol in skin care formulation

A panel of eleven voluntary human participants was recruited from within the Vantage Specialty Chemicals company. The panel was asked to evaluate commercially available antiwrinkle cream (Yves Rocher Riche Creme) into which 7 wt.% of the jojoba alcohols of Example 1 were mixed. The panel observed the following attributes:

sensory impression, skin absorption, visual wrinkle reduction (where applicable), skin reaction to the product, and customer satisfaction.

Figure 4 shows effects of the test cream on visible wrinkles in volunteers. The panel studies were first reviewed after 21 days. All panelists expressed a high level of satisfaction with the cream stating that the skin looked more radiant, more hydrated, smoother, softer, and more supple. Figure 5 shows a comparison between the time (in seconds) for skin absorption observed for the original cream compared to the time observed after administration of the cream with jojoba alcohol added. The absorption of the cream into the skin improved with the addition of jojoba alcohol.

EXAMPLE 5

Antimicrobial effectiveness of jojoba derivatives

The Antimicrobial Effectiveness Screen Test, a modification of the USP <51 > Antimicrobial Effectiveness Testing, designed and executed by the BioScreen Testing Service, Inc., was performed on jojoba oil and its derivatives, including the jojoba alcohols of Example 1 , referred to in Table 3 below as "jojoba alcohol". Cultures of bacteria Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and fungi Candida albicans and Aspergillus niger were treated with a medium containing jojoba oil or one of its various derivatives to determine their effectiveness as natural

antimicrobial agents.

The components of the hydrolyzed jojoba oil were effective antimicrobial agents tested against the studied microorganisms (Table 3).

Table 3

Claims

WE CLAIM:

1 . A product prepared by reacting a starting material comprising: (A) at least one ester comprising the residue of a fatty alcohol and the residue of a fatty acid in which each of the fatty alcohol and the fatty acid is monounsaturated and the carbon chain length of each of the fatty alcohol and the fatty acid is about 14 to about 26 carbon atoms, and the chain thereof is straight with; (B) at least one reactant which converts the ester to a mixture of (i) the fatty alcohol of said ester and (ii) a salt of the fatty acid of said ester; and separating from the mixture said fatty alcohol.

2. The product of claim 1 , wherein the starting material comprises jojoba oil.

3. The product of claim 1 or 2, wherein the jojoba oil comprises at least about 98 wt.% of a waxy ester which comprises the residue of a fatty alcohol and the residue of a fatty acid, each of the fatty alcohol and the fatty acid being monounsaturated, straight chained, and the carbon chain length of each of the fatty alcohol and the fatty acid is about 14 to about 26 carbon atoms.

4. The product according to any preceding claim comprising a liquid mixture of fatty alcohols.

5. The product according to any preceding claim comprising at least one cis- omega-9 unsaturated fatty alcohol comprising a carbon chain comprising a number of carbon atoms selected from the group consisting of 18, 20, 22, 24, and 26.

6. The product according to any preceding claim comprising a mixture of cis- omega-9 unsaturated fatty alcohols comprising carbon chain lengths of 18, 20, 22, 24, and 26.

7. The product according to any preceding claim wherein the product is

substantially free of trans-alcohol.

8. The product according to any preceding claim wherein the product is substantially free of any alcohols comprising a carbon chain having fewer than 18 atoms.

9. An emulsion comprising a liquid continuous phase having dispersed therein droplets of another liquid and further comprising the fatty alcohol of any preceding claim.

10. A method of preparing a product comprising at least one fatty alcohol comprising the steps of: a) combining jojoba oil, which comprises waxy esters that comprise the residues of straight chain, monounsaturated fatty alcohols and the residues of a fatty acids, with NaOH or KOH solution in the presence of a solvent to form a reaction mixture; b) heating the reaction mixture until the oil is completely saponified to produce (i) the fatty alcohols of said esters and (ii) a salt of the fatty acids of said esters; and c) filtering the saponified reaction mixture to separate therefrom a liquid mixture comprising the fatty alcohols in which the carbon chain thereof is monounsaturated, straight, and includes one or more carbon atoms numbering 18, 20, 22, 24, and 26..

1 1 . The method of claim 10 wherein the product comprises at least one cis-omega-9 unsaturated fatty alcohol having a carbon chain comprising a number of carbon atoms selected from the group consisting of 18, 20, 22, 24, and 26.

12. The method of claim 10 or 1 1 wherein the product comprises a mixture of cis- omega-9 unsaturated fatty alcohols having carbon chain lengths of 18, 20, 22, 24, and 26.

13. The method of claim 10, 1 1 or 12 wherein the product is substantially free of trans-alcohol.

14. The method of claim 10, 1 1 , 12 or 13 wherein the product is substantially free of any alcohols comprising a carbon chain having fewer than 18 atoms.

15. A method for preparing an emulsion according to claim 9 by forming the emulsion in the presence of an emulsifying agent which comprises the product of any of claims 1 to 8.

16. A personal care formulation comprising the product of any of claims 1 to 8.

17. A composition comprising a liquid mixture of fatty alcohols formed by saponifying jojoba oil and substantially free of fatty acids and/or salts thereof and comprising: a) 0 to about 6 wt.% of oleic alcohol; b) 35 to about 50 wt.% of Cis-1 1 -eicosenol; c) 35 to about 50 wt.% of Cis-13-docosenol; d) 5 to about 16 wt.% of Cis-15-tetracosenol; and e) 0 to about 6 wt.% of Cis-17-hexacosenol.

18. A composition according to Claim 17 wherein the amount of each of oleic acid and of C-17-hexacosenol is no greater than about 2 wt.%.

19. A personal care formulation according to claim 16 and suitable for the treatment of lips, of hair, of skin, of men's skin and hair and of miscellaneous body parts, for example, nails.

20. A personal care formulation according to claim 16 or 19 which is anhydrous (water-free).

21 . A personal care formulation according to claim 16 or 19 which is water-based.

22. A personal care formulation according to claim 16 or to any of claims 19 to 21 including about 0.01 to about 50 wt.% of the fatty alcohol.

23. A personal care formulation according to claim 16 or to any of claims 19 to 21 including about 0.01 to about 10 wt.% of the fatty alcohol.

24. An emulsion including the composition of claim 17 or 18.

25. A personal care formulation including the composition of claim 17 or 18.