ils& fats

Jojoba esters are a new category of naturally derived, oil free emollients that offer good properties for a wide variety of cosmetic products. Melanie Cummings, Kelley Dwyer and Robert Kleiman of Floratech explain

ojoba (Simmondsia chinensis) was at one time an obscure Sonoran Desert shrub known only by the deer that grazed on its foliage and

the indigenous peoples that harvested its seed for the precious oil they could obtain . For centuries jojoba has produced its unique seed and oil utilising very little water and the paucity of nutrients found in the soil of its native habitat. The plant has efficiently converted these nutrients and abundant sunshine into a versatile oil with exceptional stability and a purity of composition not duplicated by either man or nature.

The Papago tribe of present day Arizona and the Seri of Northern Mexico referred to jojoba as Jojowi, Jojoba de Sonora, goatnut, bucknut and coffeeberry. 111 Padre Kino was a Jesuit priest in the region who wrote about jojoba in 1701. He and others described

how the oil was utilised by the native people to treat wounds and burns , facilitate childbirth and enhance general skin and hair appearance .

While all other seed oils are triglycerides, the jojoba plant bears a peanut sized, dark chestnut coloured seed containing a unique oil that is chemically a liquid wax ester. 1' 1 This liquid wax ester can be rendered practically odourless and colourless, desirable qualities for cosmetic purposes. Jojoba oil is oxidatively stable and a popular cosmetic ingredient known for its non-greasy skin feel.131

At one time , sperm whale oil was a well known cosmetic ingredient with important industrial applications as well.141

For centuries the sperm whale was harvested for its oil to satisfy the needs and uses of man. In the late 1970s, the US government banned the import of sperm whale oil. Jojoba oil is touted as being similar in composition to sperm whale oil

Figure 3 - Jojoba ester differences

Product Melling point Iodine value Visual Colour oc g/l00g appearance AOCS Cc

AOCS Cc 18-80 AOCS Cd 1-25 13c-92

Jojoba esters (15) 10 - 15 78- 85 Clear, colourless liquid < 1.5 Red Jojoba esters (20) 42 - 48 64 - 70 White, creamy paste < 1.0 Red Jojoba Esters (30) 47 - 51 57 - 61 White, soft paste < 1.0 Red Jojoba Esters (60) 56 - 61 40-44 White, firm paste < 1.0 Red Jojoba esters (70) 66 - 70 <2 \%ite crystalline powder < 1.0 Red

but is in fact superior in most applications. Unlike sperm whale oil, jojoba oil has no fishy odour and no undesirable triglycerides. 1' 1

Unique composition While jojoba oil has unique and beneficial cosmetic properties its utility has been broadened significantly by using it as the base material for the creation of a new family of jojoba esters. Floraesters (INCI name: jojoba esters) are unique compositions of a broad range of saturated, partially saturated and unsaturated wax esters. Jojoba esters are made from 100% jojoba and were designed to vary in consistency from liquid to solid at ambient temperature. In the CTFA Ingredient Handbook, jojoba esters fall under the definition of a true ester and are not categorised within glyceryl esters, fats or oil families.

These jojoba esters have demonstrated the capability to improve cosmetic, functional and structural properties of a broad array of personal care products. They have shown distinctive utility in highly pigmented systems where emolliency and oxidative stability is sometimes lacking due to high levels of particulate loading.

Following the archetype of jojoba created by nature, jojoba esters are a new creation of oxidatively stable, plant­derived, oil-free emollients shown to be non-toxic, non-comedogenic, hypo­allergenic and biodegradable. Broad

Figure 1 - Jojoba ester production

Catalyst (l) + (II) - Jojoba esters

fl ,, (I) JoJob.loll

l Hydrogenalion

(II) Saturated jojoba oil

" 'o ~ (III)

~).

(IV)

ranges of physical and chemical characteristics of this new family of esters render them effective in an equally broad range of cosmetic applications.

Jojoba oil is a complex mixture consisting predominantly of 40 and 42 carbon straight-chain monoesters composed of C20 and C22 fatty alcohols and fatty acids. Each of these fatty acids and alcohols has a double bond located between the ninth and tenth carbon position from the ends of the carbon chain.

(monounsaturated) or two double bonds · (fully unsaturated).

The structure of all jojoba esters is different from its starting material - jojoba oil. It is these compositional differences within the family of jojoba esters that create their expanded utility in cosmetic preparations. Figure 2 is a listing of all ester compositions resulting from the interesterification process.

Oxidative stability Jojoba esters are more oxidatively stable than most similar cosmetic ingredients. Typically used at levels of 5-8% in formulations, the inherent stability of jojoba esters can significantly contribute to the extended shelf life of many cosmetic preparations. 191

Oxidative stability of many cosmetic ingredients can be measured to determine an Oxidative Stability Index (OSI). 1101

Jojoba esters demonstrate remarkable stability with OSI values of all jojoba esters greater than 100 hours and as high as 675 hours. The OSI of refined jojoba oil

is around 35 hours. Jojoba esters have had extensive

laboratory testing conducted to determine product safety and are recognised as non­toxic and biodegradablell. According to the Federal Safety and Health Association (FSHA), jojoba esters are not considered primary dermal irritants, are not considered ocular irritants and are not orally toxic. 02)

They do not contain heavy metals or pesticides and are also oil-free, non­comedogenic, hypo-allergenic and non­irritating. 1' 31

Clinical findings J ojoba esters provide emolliency to the skin. To support these claims, a private testing laboratory was commissioned to conduct a clinical study of four jojoba esters products. The objective of this study was to determine and compare the following properties of the products tested: • skin moisturisation (improvement,

relief and/or prevention of dry skin) Jojoba oil is converted to jojoba

esters through a process known as Figure 2 - Jojoba ester composition

Numher of interesterification. In this process, different ratios of unsaturated jojoba oil are combined with fully saturated douhle ho11<1s

jojoba oil and then interesterified. The process results in jojoba esters engineered to deliver specific physical, functional and chemical characteristics.

The jojoba ester family presently consists of the following five products: jojoba esters (15), (20), (30), (60) and (70). The utility of each product in cosmetic systems has been found to be unique.

Mother nature configured the double bonds of jojoba oil in the cis configuration. During the 'interesterification' process used to produce jojoba esters the natural cis form of jojoba remains unchanged. This interesterification route to obtaining a wide range of melting points is more desirable than the alternative of 'partial hydrogenation.' When the process of partial hydrogenation is used (instead of interesterification), the undesirable trans isomers are created. 161

Retaining the natural cis configurations during interester­ification is thought to be a key to the superior emolliency of jojoba esters produced using this interester­ification process. Interesterification produces jojoba esters engineered to contain different ratios of molecules with either no double bonds (fully saturated), one double bond

2 2 2 2 :! 2 :! 2

II

II 11 II 0 II ll I)

I)

liskr hy INCi ,\lrnhol/acid Jojoha oil

1111ml'nclalurl' c1,111hinalion

liirnscnyl ok,1tc 211:1 / rn:I X EicclSl'11)'1 eic<1scnoalc 211:1 / 211:1 X Eu,c)'I oleale 22:1 / 18:1 X Eil:oscnvl cl uc,1lc 20:1 / 22:1 X Eurc\'I cicose110i1ll' 22:1 / 211:1 X Tel1 i1cosanyl oleak 2•1:l / 18:1 Tet l'ilCtJSimyl cicoscnoale 2•1:1 / 211:1 X

l·:urcyl cruc,,le 22:1 / 22:1 X TL'l1 i1co:,;anyl crucatc 2•1:1 / 22:1 Eicoscnvl stcaralc 211:l / 18:O

Eicosl'nyl olci1lc 211:O / 18:1

Eicoscrwl ekoscnoate 211:11211:11

Eicosl'nyl l'icosl'noatc 211:11 / 211:I

l•:11rL\'l slearalc 22:1 / 18:11

Behenyl ole;,le 22:11 / 18:I

EiLosenyl hd1cnatc 211:l / 22:II

EiC(ISL'llyl l') llCilll' 211:11 / 22:1

Eurcyl cicosc1wak 22:1 / 211:11

lkhl'nvl eil'tlSl'noall' 22:11 /211:1

TL'l I i1cos;111yl stc;1r:1Lt- :!,l:1 I 18:11

Td r:1cos;111yl I deall' 2.l:()/ 1,~:l

Tclri1C1Jsanyl ciccJSl'll(Jitll' 2.\:I / 211:11

TL"l1 ;1c(1s;1nyl l'icosl'rn1alc 2-1:11/211:l

Eurcyl hehcn;,lc 22:1 / 22:11 Bel,cnyl eruc;,te 2:!:0 / 2:!:1

Tl'.lli1C(1Silll)'i hchl'ni1le 2-l: 1122:11

Tclr.:u.:os.:111yl l'l'UCitll' :!-l:11 / 22:1

EicoSl'll\'I slei1l'i11l- 211:11 / 18:11

Eic11Sl'll)'I cic11Sl'll1,:1tc 211:11 / 20:11 lkhcnvl ste;,r;,k 22:11118:11

Eic11sl'nyl hl·lll'n<tll' 211:11 / 22:11

lklll'n\'l l0 irosL·1w:1k 22:O / 211:11

Td1:1rosa11yl slei1li1ll' 21:11 / lH:11

Tel 1 ;1c1 is;1nyl l'ic11st.:rn,;1lc 2.\:11 / 211:11

tkh,·111'I hclwnale :!:!:II/ 22:11

Tdr;1c(1."illl)'I hehl'Jliill' :!-~:O / 22:0

Total number of esters 7

Jojoba Jojoba

esters (15) esters (211)

X X X X X X X X X X X X X X X X X X

X X X X X X X X X X X X X X X X X X

9 27

Jojoh;, esters )

(:lO) &((ill

X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X

36

Jojoh.i

eslrs (70)

X X X X X

X X

7

A

B

C

• skin smoothing and softening (ie reduce roughness)

• skin texture improvement (ie reduce roughness and scaliness)

• skin firmness and elasticity improvement and/or maintenance Overall, the study results indicated that

jojoba esters (20), (30) and (60) were able to moisturise and soften the skin as well as improve skin texture. These products, in addition to jojoba esters (70), were able to improve skin firmness and, at various time points, reduce fine lines. Copies of all protocols and results are available upon request.

Skin replica analysis indicates that all product sites experienced significant reductions in fine lines at some point after jojoba ester application. In general, jojoba esters (20) and (30) effectively reduced fine lines for up to one hour, after which they reached a plateau. Jojoba esters (60) showed the most even reduction of fine lines over time while jojoba esters (70) showed the greatest fine line reduction between one and five hours.

Dermaflex-A™ (Cortex Technologies, Denmark) testing protocol demonstrated that all jojoba esters tested were able to significantly reduce skin distensibility. A reduction in skin distensibility is inversely related to skin firmness (ie reduced distensibility indicates increased firmness).

Lipstick applications A basic lipstick formula was modified to compare the differences among lipsticks containing identical concentrations of jojoba oil, jojoba esters (15), jojoba esters (20), and jojoba esters (30). Figure 4 lists the ingredients and quantities used in each formulation. In the four formulas, 15% of the castor oil was replaced in each formula with either jojoba oil, jojoba esters (15), jojoba esters (20), or jojoba esters (30).

A questionnaire was completed by

Figure 4 - Lipstick formula comparisons each panellist to document the findings and the results

Ingredients Jojoba oil

Castor oil 41.0 Jojoba oil 15.0 Jojoba eslers (15) 0.0 Jojoba esters (20) 0.0 Jojoba esters (30) 0.0 Jojoba esters (70) 1.0 Carnauba wax Nol Yellow 4.0 Candelilla wax 5.0 Beeswax 3.5 Microcr)'slalline wax 4.0 Propylparaben 0.1 Cabosil M-5 0.2 Castor oil 13.0 Arlacel P-100 0.5 Tilanium dioxide 5.5 Pur Oxy Red 4.0 D&C Hetl No30, Talc Lake 2.5 FD&C Blue N No!Aluminum Lake 0.1 Black iron oxitle 0.5 Tenox GT-2 0.1 Total: 100.0

Jojoba esters (15)

41.0 0.0

15.0 0.0 0.0 1.0

4.0 5.0 3.5 4.0 0.1 0.2

13.0 0.5 5.5 4.0

2.5

0.1 0.5 0.1

100.0

Jojoba Jojoba were tabulated. For esters (20) esters (30)

41.0 0.0 0.0

15.0 0.0 1.0

4.0 5.0 3.5 4.0 0.1 0.2

13.0 0.5 5.5 4.0

2.5

0.1 0.5 0.1

100.0

41.0 0.0 0.0 0.0

15.0 1.0

4.0 5.0 3.5 4.0 0.1 0.2

13.0 0.5 5.5 4.0

2.5

0.1 0.5 0.1

100.0

example, the findings demonstrated that if a glossier, more easily applied lipstick with better coverage is desired, then jojoba esters (15) and jojoba oil are ideal candidates. If a longer wearing, matte lipstick with the capability to draw a more precise line is preferred, then jojoba esters (30) contributes these desirable attributes. Depending on the desired lipstick property, there is a jojoba ester product that can satisfy the formulation need.

Preparation - Combine ingredients o( phase A and heal lo 85"C with motlerale agilalion. Combine phase 13 and pass Lwice Lhrough a 3-roll mill. Add phase B to phase A with propeller agitation.

One specific benefit of using jojoba esters in lipstick is that emolliency and stick strength can be maintained even with a reduction in wax

ils& fats

Formulation I - Castor Oil Free Lipstick

Ingredients % wt/wt

/\ Hybrid sunflower (Helian//ws .•\muws) Oil 11.4 Macadamia tcrnifolia nul oil 22.0 Jojoba esters (:lO) 17.0 Jojoba esters (7fl) 1.0 Carnauba (Copemicia cerifera) wax 4.0 Candclilla tfuphorbia cerifera) wax 5.0 Beeswax 3.5 Microcryslalline wax 4.0 Polybutene 5.0 Propylparaben qs Silica 0.5

ll Hybrid sunflower (Helianlhus annuus) oil 13.0 Polyhydroxyslearic acid 0.5 Titanium dioxide 5.5 Iron oxides 4.5 D&C Red No 30 Talc Lake 2.0 FD&C Blue Nol Aluminum Lake 0.1 Iron oxides 0.5

C Tocopherol 0.1 Pragrance qs

Total: 100.0

Preparation - Combine ingredients of phase A and heat lo 85C with moderate agitation. Combine phase Band pass twice through a three roll mill. Atld phase ll to phase A with propeller agitation. Cool batch lo 75C, add phase C and mix with propeller agitation. Pill as soon as possible.

content. 1' 41 Laboratory studies showed lipstick strength was increased by greater than 20% in 71 % of the trials if 9% of jojoba esters are substituted for half (9%) of the base wax of the lipstick formula. Jojoba esters are as stable as castor oil but have none of the negative marketing attributes of castor oil and are perceived by consumers as being pleasanter on the lips as compared to castor oil

Formulation 1 illustrates a lipstick formula in which all the castor oil has been replaced with jojoba esters and other botanical emollients. The cosmetic properties of this formulation of castor oil-free lipstick are superior to the castor based control. Marketers of jojoba ester­based lipsticks can avoid the negative attributes of castor oil.

Other applications Jojoba esters have been used in almost every type of personal care product from hair care products to colour cosmetics. Jojoba esters provide emolliency, oxidative stability, improved and increased stick structure, improved colour payout and more uniform pigment dispersion. They can be used as an oxidatively stable botanical alternative to synthetic waxes and esters.

Functionalities for jojoba esters in

cosmetic applications include: • pigment wetting/binding • contribution of slip, gloss and

moisturising effects in lipsticks • replacement for castor oil in lipsticks • contribution of emolliency in highly

pigmented cosmetic systems For example, Jojoba esters have been

found to be of unique utility in mascara and eyeliner formulations, eye shadow, lipstick and fluid foundations.

One of the most remarkable attributes of this odourless, colourless family of emollients is its extended oxidative stability when compared to similar cosmetic ingredients. Jojoba esters are non-comedogenic, hypo-allergenic, non­toxic, non-irritating and have been found to be effective in reducing fine lines while increasing skin firmness. They contribute emolliency to highly pigmented systems such as lipsticks and mascara and combinations of jojoba esters can act as substitutes for castor oil in lipsticks, while improving different lipstick attributes such as gloss, matte, payout and coverage.

Contact Floratech, USA. Tel: + 1 480 545 7000. Fax: +1 480 892 3000.

floratech.com

ils& fats

References

1. Salunke D K, Chavan J V, Adsule RN & Kadam S S, World oilseeds chemistry, technology and utilisation, Van Nostrand Reinhold, New York, p489-490 (1992)

2. Wisniak J, The chemistry and technology of joi(!ba oil, American Oil Chemists' Society, p 1-3 (1987)

3. Wisniak, J Ibid, pp 252-254 4. linam D, Jojoba fever, Burbank Books, 1981 5. Kleiman R, Chemistry of new industrial oilseed crops, advances in new crops,

Timber Press, Portland OR, p196-203 (1990) 6. Judd JT, "Studies show negative trans effects" Inform Vol 9 No 12 pll80

(Dec 1998) 7. American oil Chemists' Society 8. Inductively-coupled plasma atomic emission spectroscopy 9. Arquette D I, Cummings M, Dwyer K, Kleiman R & Reinhardt J, A natural oil

made to last, Cosmetics and Toiletries, Vol 112 pp 67-72 (1997) 10. American Oil Chemists' Society method Cd 12b-92 11. National Research Council 1985 Jojoba: New crop for arid lands, New material

for industry. National academy press, Washington, DC pg 39 12. Cosmetic Ingredient Review, Washington DC p73 (1.985) 13. Arquette DJ, ,Bailyn EM, Palenske J, DeVom Bergman D & Rheins LA, Non­

comedogenic and hypoallergenic properties of jojoba oil and hydrogenated jojoba oil JSCC, vol 49 p377-383 (Nov/Dec 98)

14. Arquette J, Cummings M & Reinhardt J, Jojoba esters in lipsticks, Cosmetics and Toiletries, vol 113 p63-65 (1998)

f LORA TECH SIHCE 1915

♦ Plant Derived

♦ Non GMO

♦ Long Shelf Life

♦ All Products Approved in Japan

AMERICAS • EUROPE • ASIA

Reprinted from SPC Asia May 1999

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