WO2025196161A2

WO2025196161A2 - Cosmetic compositions, use thereof, and methods for using such compositions

Info

Publication number: WO2025196161A2
Application number: PCT/EP2025/057575
Authority: WO
Inventors: Konstantin Nikolaev GOLEMANOV; Pierre-Emmanuel Dufils; Silvia Helena GUERRA DOS SANTOS; Vincent MIRALLES
Original assignee: Quimicos E Solucoes Sustentaveis Do Brasil SA; Specialty Operations France SAS
Current assignee: Quimicos E Solucoes Sustentaveis Do Brasil SA; Specialty Operations France SAS
Priority date: 2024-03-20
Filing date: 2025-03-20
Publication date: 2025-09-25
Anticipated expiration: 2026-09-20
Also published as: WO2025196161A3

Abstract

The present invention relates to cosmetic compositions, in particular to hair care or skincare compositions. It also relates to use and methods for using such compositions, in particular to hair care or hair conditioning compositions or skin care compositions based on vegetable oils and a co-active substance.

Description

COSMETIC COMPOSITIONS, USE THEREOF, AND METHODS FOR USING SUCH COMPOSITIONS

The present invention relates to cosmetic compositions. In particular, the present invention relates to hair care or skincare compositions as well as use and methods for using such compositions. In particular, the present invention relates to haircare or hair conditioning compositions based on vegetable oils and a co-active substance.

The present invention also relates to compositions which are effective for skincare, for example as emollients, skin repair creams, moisturizing creams and ointments, and related products.

In particular the present invention relates to hair care compositions exhibiting both conditioning and cleansing properties for the simultaneous washing and conditioning of the hair.

For example, shampoo compositions based essentially on conventional surface-active agents of, in particular, anionic, non-ionic and/or amphoteric type, are used for washing the hair.

These compositions are applied to wet hair and the foam generated by massaging or rubbing with the hands makes it possible, after rinsing with water, to remove dirt initially present on the hair.

Although having good washing power, these base compositions possess cosmetic properties that remain fairly weak, in particular as the relatively aggressive nature of such a cleansing treatment can result, in the long term, in more or less marked damage to the hair, damage related in particular to the gradual removal of the lipids or proteins present in or at the surface of the hair.

This is the reason why most of the hair care compositions further comprise additional cosmetic agents known as conditioners or conditioning agents, which are intended mainly to repair or limit the harmful or undesirable effects brought about by the various treatments or attacks to which keratinous materials are more or less repeatedly subjected. These conditioners can also improve the cosmetic behavior of the keratinous materials.

The most commonly used conditioning agents, especially in hair care formulations, are cationic polymers, cationic surfactants, silicones and/or silicone derivatives. In recent times there is an increasing demand for hair care compositions with higher cosmetic performance, allowing “one shot” washing and conditioning of the hair and including safe, environment friendly and/or natural ingredients.

Further, there is a demand for skincare products which enable skin protection and care.

Several formulations have been tested in the literature, but it remains a challenge to find out a formulation providing a cosmetic performance, notably in terms of softness, detanglability, shine, spreadability, along with cleansing, while being stable over time (no separation of phases).

Generally speaking, the presence of relatively high amounts of cleansing agents in the hair conditioning formulations has the adverse effect to cause phase separation. Viscosity can also be affected in those cases.

This is the reason one of the major challenges when incorporating relative high amounts of cleansing agents into a hair conditioning composition is to benefit from the cleansing and conditioning properties while maintaining satisfactory softness, detanglability, shine, spreadability, along with cleansing properties and without negatively impacting viscosity and/or stability of the overall composition.

It is thus a particular object of the present invention to address the ever increasing demand in the market for hair care cleansing and conditioning compositions that contain relative high amounts of cleansing agents, while maintaining satisfactory viscosity, stability and conditioning properties.

Another object of the present invention is to provide skin care and hair care compositions, for example, hair or skin cleansing and conditioning compositions. Another object of the invention is to provide hair care compositions which exhibit good conditioning properties, such as ease of detangling, softness and shine properties, and a satisfactory viscosity.

The present invention also relates to use of the cosmetic compositions as well as to a method for preparing a chemically modified vegetable oil, which can be used in the aforementioned cosmetic compositions, and to a chemically modified vegetable oil obtained by said process.

General definitions

Before the invention is described in detail, it is to be understood that this invention is not limited to specific process conditions described herein, since such conditions may, of course, vary. It is also to be understood that the terminology used herein is not intended to be limiting, since the scope of the present invention will be limited only by the appended claims.

As used herein, the singular forms "a", "an", and "the" include both singular and plural referents unless the context clearly dictates otherwise. By way of example, "a compound" means one compound or more than one compound.

The terms "containing", "contains" and "contained of as used herein are synonymous with "including", "includes" or " comprising", "comprises", and are inclusive or open-ended and do not exclude additional, non-recited members, elements or process steps. It will be appreciated that the terms “containing”, “contains”, "comprising", "comprises" and "comprised of as used herein comprise the terms "consisting of, "consists" and "consists of .

Throughout this application, the term "about" is used to indicate that a value includes the standard deviation of error for the device or method being employed to determine the value.

As used herein, the term “average” refers to number average unless indicated otherwise.

As used herein, the terms “% by weight”, “wt.-%”, “weight percentage”, or “percentage by weight” are used interchangeably. The same applies to the terms “% by volume”, “vol.- %”, “vol. percentage”, or “percentage by volume”, or “% by mol”, “mol- %”, “mol percentage”, or “percentage by mol”.

The recitation of numerical ranges by endpoints includes all integer numbers and, where appropriate, fractions subsumed within that range (e.g. 1 to 5 can include 1, 2, 3, 4 when referring to, for example, a number of elements, and can also include 1.5, 2, 2.75 and 3.80, when referring to, for example, measurements). The recitation of end points also includes the end point values themselves (e.g. from 1.0 to 5.0 includes both 1.0 and 5.0). Any numerical range recited herein is intended to include all sub-ranges subsumed therein.

All references cited in the present specification are hereby incorporated by reference in their entirety. In particular, the teachings of all references herein specifically referred to are incorporated by reference.

Unless otherwise defined, all terms used in disclosing the invention, including technical and scientific terms, have the meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. By means of further guidance, term definitions are included to better appreciate the teaching of the present invention.

In the following passages, different alternatives, embodiments and variants of the invention are defined in more detail. Each alternative and embodiment so defined may be combined with any other alternative and embodiment, and this for each variant unless clearly indicated to the contrary or clearly incompatible when the value range of a same parameter is disjoined. In particular, any feature indicated as being preferred or advantageous may be combined with any other feature or features indicated as being preferred or advantageous.

Furthermore, the particular features, structures or characteristics described in present description may be combined in any suitable manner, as would be apparent to a person skilled in the art from this disclosure, in one or more embodiments. Furthermore, while some embodiments described herein include some but not other features included in other embodiments, combinations of features of different embodiments are meant to be within the scope of the invention, and from different embodiments, as would be understood by those in the art.

Should the disclosure of any patents, patent applications, and publications which are incorporated herein by reference conflict with the description of the present application to the extent that it may render a term unclear, the present description shall take precedence.

As used herein, and unless otherwise indicated, the term "about" or "approximately" means an acceptable error for a particular value as determined by one of ordinary skill in the art, which depends in part on how the value is measured or determined. In certain embodiments, the term "about" or "approximately" means within 1, 2, 3, or 4 standard deviations. In certain embodiments, the term "about" or "approximately" means within 50%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%), 1%), 0.5%), or 0.05%) of a given value or range.

Also, it should be understood that any numerical range recited herein is intended to include all sub-ranges subsumed therein. For example, a range of " 1 to 10" is intended to include all sub-ranges between and including the recited minimum value of 1 and the recited maximum value of 10; that is, having a minimum value equal to or greater than 1 and a maximum value of equal to or less than 10. Because the disclosed numerical ranges are continuous, they include every value between the minimum and maximum values. Unless expressly indicated otherwise, the various numerical ranges specified in this application are approximations.

Disclosure of the invention

The Applicant has now discovered unexpectedly that a cosmetic composition containing a particular combination of a vegetable oil and a chemically modified oil compound makes it possible to achieve the objective as outlined above. Moreover, it has been discovered that the specific combination of a vegetable oil and a coactive substance in the cosmetic compositions of the invention has synergistic activity in terms of beneficial effects for haircare and skincare.

In particular, the cosmetic compositions of the invention may provide a synergistic effect due to the particular combination of the oil and co-active substance with respect to in vivo/invitro sensorial performance, deposition of active, hydrophobization of the hair fiber, and/or spreading on the surface.

In particular, the compositions of the invention can show increased performance in combing tests (in vivo tests), deposition of conditioning substances on hair fibers, and/or hydrophobization of the fibers by the composition (as measured via the contact angle). Moreover, it is possible to formulate mixtures with favourable properties such as good long-term stability and high transparency. Moreover, it is possible to provide cosmetic compositions which are essentially free of silicone oil.

Brief Description of Figures

Figure 1 shows measurement results for determining the contact angle of a composition of the present invention.

Figure 2 explains the measurement of wet combing, as explained in the Materials and Methods section below.

Summary of the invention

The above objectives are solved by means of the following aspects of the invention.

In particular, the invention provides cosmetic compositions which comprise (A) one or more vegetable oil(s) and (B) one or more co-active substance(s), wherein the co-active substance (B) is one or more chemically modified oil, selected from the group, consisting of (i) oil oligomers derived from triglycerides or liquid esters, (ii) oil-based estolides derived from triglycerides or liquid esters, and (iii) linear or branched hydrocarbons.

As used herein with reference to the present invention, the (i) oil oligomers derived from triglycerides or liquid esters shall refer to the oligomers resulting from the reaction between a triglyceride or a liquid ester with one or more monofunctional fatty acid. The molecule obtained corresponds to the starting triglyceride or to the liquid ester grafted with one or more fatty acids, as illustrated below:

As used herein with reference to the present invention, the (ii) oil-based estolides derived from triglycerides or liquid esters shall refer to the oil-based estolides resulting from the reaction between triglycerides or liquid esters with one or more molecules carrying at least two carboxylic acids. The molecule obtained corresponds to the condensation of the triglycerides or liquid esters via the difunctional molecules, as illustrated below:

The present invention provides skincare and haircare compositions comprising a mixture of (A) one or more vegetable oil(s) and (B) one or more coactive substance(s), wherein the co-active substance (B) is as defined above, as well as several aspects of use for said cosmetic composition.

The composition comprises a vegetable oil. Preferably, the vegetable oil is one or more, selected from the group, consisting of Coriander seed oil, Groundnut oil, Rice bran wax, Evening primrose oil, Apricot kernel oil, Grapeseed oil, Rice bran oil, Linseed oil, Mongongo oil, Hibiscus oil, Babassu seed oil, Hazelnut oil, Wheatgerm oil, Baobab oil, Rose flower oil, Corngerm oil, Walnut seed oil, Canola (Rapeseed) oil, Brazil nut oil, Baobab seed oil, Moringa Oleifera Seed oil, Camelina sativa seed oil, Babassu nut oil, Camellia oil, Macadamia Integrifolia S. oil, Crambe oil, Manila oil, Sesame seed oil, Macadamia Ternifolia S. oil, Soybean oil, Avocado oil, Jojoba seed oil, Safflower oil, Shea butter, Argan oil, Guar oil, Coconut oil, Mango oil, Pracaxi oil, Pumpkin Seed oil, Grape Seed oil, Pequi oil, Passion Fruit oil, Amaranthus oil, Kokum oil, Cassia oil, and Sunflower oil.

The vegetable oil (A) can comprise(s) one or more of monoglycerides, diglycerides, triglycerides, mixtures of mono- di- and triglycerides, and/or liquid esters.

Accordingly, the above vegetable oils can be used as a mixture of monoglycerides, diglycerides, triglycerides, mixtures of mono- di- and triglycerides. Many vegetable oils comprise a major content of triglycerides. It is also possible to chemically modify the triglyceride content and to increase the diglyceride content by means of the method described in the Experimental section below. Hence, the vegetable oils can be used as supplied or after modification by means of glycerolysis as described below in the Examples Section.

The composition of the invention also comprises a co-active substance or coactive ingredient. Preferably, the co-active substance (B) is a chemically modified oil. Moreover, the co-active substance can be (i) oil oligomers derived from triglycerides or liquid esters, (ii) oil-based estolides derived from triglycerides or liquid esters, and (iii) linear or branched hydrocarbons.

The aforementioned composition preferably comprises one or more co-active substances, selected from the group, consisting of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/dicarboxylic acid copolymer (and) Cs-Cw carboxylic acid.

In the aforementioned composition, the vegetable oil (A) is preferably one or more, selected from the group, consisting of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Jojoba oil, Cassia oil, Argan oil, Coconut oil, Rice Bran oil, and Crambe oil, more preferably from the group consisting of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Argan oil, and Coconut oil.

In the aforementioned composition, the vegetable oil (A) is preferably one or more, selected from the group, consisting of Avocado oil, Guar oil, Amaranthus oil, Baobab oil, and wherein the co-active substance (B) is one or more, selected from (i) oil oligomers derived from triglycerides or liquid esters, (ii) oil-based estolides derived from triglycerides or liquid esters, and (iii) linear or branched hydrocarbons. In one or more embodiments, the vegetable oil (A) is preferably one or more, selected from the group, consisting of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Argan oil, and Coconut oil, and wherein the co-active substance (B) is one or more, selected from (i) oil oligomers derived from triglycerides or liquid esters, (ii) oil-based estolides derived from triglycerides or liquid esters, and (iii) linear or branched hydrocarbons. More particularly, the co-active substance can be selected from dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and C8-C14 carboxylic acid.

Preferably, the co-active substance (B) is selected from the group, consisting of Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride.

Moreover, in the aforementioned composition, the oil-based estolides (ii) are preferably derived from vegetable oil triglycerides or liquid esters, optionally grafted with fatty acids with a length of 6 or 12 carbon atoms. Preferably, the oil based estolides (ii) are derived from Lauric acid and epoxidized triglycerides polyester, lauric acid and epoxidized jojoba oil polyester, hexanoic acid and epoxidized triglycerides polyester, hexanoic acid and epoxidized jojoba oil polyester, and hexanoic acid and epoxidized jojoba oil polyester.

Preferably, the vegetable oil is one or more, selected from the group, consisting of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Argan oil, and Coconut oil, more preferably from the group consisting of Avocado oil, Baobab oil, Guar oil, Amaranthus oil.

In a preferred embodiment, the weight ratio of the vegetable oil (A) to the co- active substance (B) can be 40:60 to 70:30, preferably 50:50.

The present invention also provides skincare or haircare compositions, comprising the cosmetic composition as defined herein.

The aforementioned composition preferably further comprises one or more ingredients, selected from the group, consisting of a pH regulating system, emollient(s), excipient(s), a surfactant system, guar, rheology modifier(s), antioxidant(s), conditioning polymer(s) and solubilization agent(s), said composition preferably comprising citric acid in a pH regulating system, said composition more preferably comprising cationic/non cationic surfactant(s) in an amont from 10% to 25% by weight, based on 100% total weight of the composition.

The aforementioned composition preferably further comprises a sulfated or non-sulfated chassis.

Preferably, the aforementioned composition has a silicone oil content of 0,001 % or less based on the total weight of the composition.

The content of the vegetable oil (i) and the active substance (ii) can be 0,1- 20%, preferably 0,25-5%, more preferably 0,5-2%, based on the total weight of the composition.

The present invention also provides the use of the aforementioned composition in hair care compositions, preferably in hair conditioning compositions, preferably wherein said use is for increasing hair hydrophobicity.

Further, the present invention provides the use of a composition according to the invention in skincare or haircare compositions.

The present invention also provides a method for preparing a chemically modified vegetable oil, said method comprising (i) a glycerolysis step comprising reacting a vegetable oil with glycerin using a lipase as catalyst, and (ii) an esterification step comprising esterification of the product of step (i) with a dicarboxylic acid.

Preferably, in the aforementioned method, the vegetable oil is selected from the group, consisting of Coconut oil, Babassu oil, Crambe oil, Pequi oil, Mango oil, Grape oil, Maracuja oil, Pumpkin Seed oil and Pracaxi oil, and/or the dicarboxylic acid is selected from the group, consisting of adipic acid and sebacic acid.

The present invention also provides a chemically modified vegetable oil obtained by the process described herein.

Description of preferred embodiments

Vegetable oils

The present invention relates to cosmetic compositions comprising vegetable oils. As is commonly known, vegetable oils, also referred to as vegetable fats, are oils extracted from seeds or from other parts of fruits. Like animal fats, vegetable fats are known as mixtures of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oils, or fats from seeds. Olive oil, palm oil, and rice bran oil are examples of fats from other parts of fruits. In common usage, vegetable oil may sometimes refer to vegetable fats which are liquid at room temperature. Many vegetable oils are edible. The vegetable oil of the present invention can be a synthetic or naturally occurring vegetable oil. In particular, the vegetable oil according to the invention can be one or more vegetable oils. A vegetable oil used in the composition of the invention may also comprise a certain amount of another vegetable oil, depending on the content specific case and the purity.

Preferably, the vegetable oil comprises one or more vegetable oils, selected from the group consisting of Coriander seed oil, Groundnut oil, Rice bran wax, Evening primrose oil, Apricot kernel oil, Grapeseed oil, Rice bran oil, Linseed oil, Mongongo oil, Hibiscus oil, Babassu seed oil, Hazelnut oil, Wheatgerm oil, Baobab oil, Rose flower oil, Comgerm oil, Walnut seed oil, Canola (Rapeseed) oil, Brazil nut oil, Baobab seed oil, Moringa Oleifera Seed Oil, Camelina sativa seed oil, Babassu nut oil, Camellia oil, Macadamia Integrifolia S. Oil, Crambe oil, Manila oil, Sesame seed oil, Macadamia Temifolia S. Oil, Soybean oil, Avocado oil, Jojoba seed oil, Safflower oil, Shea butter, Argan oil, Guar oil, Coconut oil, Mango oil, Pracaxi Oil, Pumpkin Seed Oil, Grape Seed Oil, Pequi Oil, Passion Fruit Oil, Amaranthus oil, Kokum oil, Cassia oil, and Sunflower oil.

In a preferred embodiment, the vegetable oil is one or more of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Argan oil, and Coconut oil, preferably Avocado oil, Baobab oil, Guar oil, Amaranthus oil.

The oils can be used as supplied or can be prepared in known procedures.

All amounts are in % by weight of active relative to the total weight of the composition. The term “active weight” means the real weight of active, and not the total weight of product as it is. For example, the active weight of 1.5g of a given raw materials that is 80% active, in fact 1.2g.

The present invention is also directed toward the use of such a composition which can be used, for example, for simultaneously washing and conditioning the hair.

Surprisingly it has been found that the specific surfactant combination in the specific ratio according to the invention makes it possible to achieve at the same time an acceptable compromise between the following attributes: viscosity of the composition, cleansing properties and conditioning properties, while maintaining stability. For example, the cosmetic compositions according to the invention are able to provide excellent conditioning effects such as increased hydrophobicity to the hair.

Fibers with higher hydrophobicity are less adhesive one towards the other. They separate more easy, which leads to a free-flowing hair which is easy to manage.

The compositions of the invention can confer on the hair, a noteworthy treating effect which is revealed in particular by an ease of detangling, as well as a contribution on softness and shine without major feeling of greasiness.

Preferably, the composition has a satisfactory viscosity. By the expression "composition having a satisfactory viscosity" it is meant here a composition that has an apparent viscosity comprised between 5,000 and 12,000 cps, for instance comprised between 7,000 and 11,000 cps, for instance comprised between 8,000 and 11,000 cps, for instance comprised between 9,000 and 10,000 cps cps. The apparent viscosity of each composition was as indicated in the Material and Methods section.

By the expression "conditioning the hair" or “improved conditioning” it is meant the improvement of ease of detangling and/or ease of combing, softness and/or shine.

Ease of detangling may be determined by the measurement of the time required for detangling the hair by using the wider teeth of a comb. The shorter the detangling time, the easier to detangle the hair is.

Ease of combing may be determined by the measurement of the work required for combing the hair by using the wider teeth of a comb. The lower the combing work, the easier to comb the hair is.

Softness, or hair feel, and shine may be assessed by an expert panel using sensorial tests on hair care on length and tips.

The composition of the invention is a hair care composition, preferably a hair conditioning and cleansing composition, also called “cleansing conditioner”.

Elsewhere in the specification and claims, individual numerical values, or limits, can be combined to form additional non-disclosed and/or non-stated ranges.

For the avoidance of any doubt the amounts of surfactant refer to the actual amount of active surfactant compound present in the composition. In other words, it does not include the residue which may be present as an impurity in a commercially available surfactant mixture, or water when presenting in an aqueous solution.

Co-active substance

The active ingredient of the cosmetic composition of the present invention is a combination of a vegetable oil (A), as noted above, and a chemically modified oil (B) as a co-active substance.

Among the co-active substances, preferable are (i) oil oligomers derived from triglycerides or liquid esters, (ii) oil-based estolides derived from triglycerides or liquid esters, and/or (iii) linear or branched hydrocarbons.

Oil oligomers derived from triglycerides can be prepared by glycerolysis as described in the Examples section. For instance, the diglycerides obtained from glycerolysis can be used as active substances according to the invention.

Another example of chemically modified oil compounds useful in the invention is the (ii) oil based estolides.

Oil-based estolides as referred to herein are oligomeric esters derived from a vegetable oil, and contain special fatty acid with an additional functional group. They cover a wide range of viscosity and, by virtue of their adaptable molecule, can have product properties that vary within a spectrum of above-average width. The scheme below shows the basic structure of an estolide. In the example below, a hydroxy-fatty acid forms the basis of the estolides which is able to form oligomers at first by self-esterification. The estolide number (EN) represents the degree of oligomerization. The hydroxy acids used may come from natural sources, for example. This is available as such or in its hydrogenated form. Alternatively, a hydroxy acid may be obtained from unsaturated fatty acids using mineral acids as a catalyst. The oligomerization reaction is terminated by a capping fatty acid which offers the ability to influence the product properties. The resulting estolide still has a free acid group on the starting fatty acid which can be further esterified with alcohols, e.g. linear or branched alcohols.

In the cosmetic compositions of the invention, the oil-based estolides (ii) as co-active substances are preferably derived from vegetable oil triglycerides or liquid esters, optionally grafted with fatty acids with a length of 6 or 12 carbon atoms, and/or the oil based estolides (ii) are preferably derived from lauric acid and epoxidized triglycerides polyester, lauric acid and epoxidized jojoba oil polyester, hexanoic acid and epoxidized triglycerides polyester, hexanoic acid and epoxidized jojoba oil polyester, and hexanoic acid and epoxidized jojoba oil polyester.

Preferably, the co-active substance used in the invention is chosen from one or more of sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized Jojoba oil polyester, and hydrogenated Castor oil / hydrogenated Castor oil/Adipic Acid Copolymer / Caprylic/Capric Triglyceride.

A preferred co-active compound is (iii) a linear or branched hydrocarbon. Preferably, the hydrocarbon is one or more of liquid or solid hydrocarbons, oils or waxes, and can be selected from one or more C6-C90 straight or branched hydrocarbons. For example, the hydrocarbons can be selected from straight or branched Ce-Ceo hydrocarbons. Further examples for hydrocarbons are one or more of decane, dodecane, tetradecane, distillates (Fischer-Tropsch): heavy, Cl 8-50- branched, cyclic and linear, CAS: 1262661-88-0, isooctane, squalene and squalene.

Another co-active substance is Dermalcare AD208® supplied by Syensqo (diethylhexyl adipate).

The co-active ingredient is preferably present in an amount of 0,1-20% by weight, preferably 0,5-2%, more preferably 0,5-1%, based on the total weight of the composition. Preferably, the co-active ingredient, or the mixture of the vegetable oil and the co-active substance (co-active ingredient) can be present in 0,1%, 0,15%, 0,20%, 0,25%, 0,30%, 0,35%, 0,40%, 0,45%, 0,50%, 0,55%, 0,60%, 0,65%, 0,70%, 0,75%, 0,80%, 0,85%, 0,90%, 0,95%, 1,00%, 1,05%, 1,10%, 1,15%, 1,20%, 1,25%, 1,30%, 1,35%, 1,40%, 1,45%, 1,50%, 1,55%, 1,60%, 1,65%, 1,70%, 1,75%, 1,80%, 1,85%, 1,90%, 1,95%, 2,00%, 2,1%, 2,2%, 2,3%, 2,4%, 2,5%, 2,6%, 2,7%, 2,8%, 2,9%, 3,0%, 3,1%, 3,2%, 3,3%, 3,4%, 3,5%, 3,6%, 3,7%, 3,8%, 3,9%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19% or 20% by weight, based on the total weight of the composition. Silicone oil content

The compositions of the invention may contain one or more silicone oils, or can be silicone oil free compositions. Preferably, the compositions of the invention are free of silicone oil. Preferably, silicone oil free compositions contain less than 0,001% by weight of silicone oil. More preferably, the compositions contain less than 0,0005%, less than 0,0001%, less than 0,00005%, less than 0,00001%, less than 0,000005%, or less than 0,000001% of silicone oil, based on the total mass of the composition. Preferably the compositions contain less than 5 ppm, less than 1 ppm, less than 0,05 ppm, less than 0,01 ppm, or less than 0,001 ppm of silicone oil.

Weight ratio

A parameter of the composition of the present invention which may have an influence on its properties is the active weight ratio of the vegetable oil to the coactive substance (A) / (B).

It is assumed that this ratio can be connected with technical effects in terms of stability at low temperature, odour, viscosity.

The weight ratio can, for instance, be 40/60, 50/50, 60/40 or 70/30. The ratio is advantageously 1 : 1. Advantageously, the active weight ratio of the vegetable oil to the co-active ingredient is 45:55, 65:45, 41 :59, 42:58; 43:57, 44:5,46:54, 47:53, 48:52, 49:51, 50:50, 51 :49, 52:48, 53:47, 54:46, 55:45, 56:44, 57:43, 58:42, 59:41, 60:40, 61 :39, 62:38, 63:37, 64:36, 65:35, 66:34, 67:33, 68:32, 69:31, or 70:30.

A particularly preferred range for the active weight ratio is between 40/60 to 50/50.

For example, the composition can be prepared from a vegetable oil (A) and a co-active substance (B) in a mass ratio of 1 : 1, and formulated in shampoo surfactant chassis at a total concentration of 1 %.

An exemplary formulation may include 8-10% of one or more anionic surfactants, 2-3% of one or more amphoteric surfactant, 2-4% of one or more thickeners, 1% of one or more emulsifying agents, 1% of one or more active agents (i.e. vegetable oil (A) and co-active substance (B)), less than 1% of one or more preservatives, less than 1% of one or more antioxidants, and one or more pH adjusters (q.s. to e.g. pH=5; e.g. citric acid), and water (q.s. to 100%).

Preferred combinations of vegetable oil (A) and co-active substance (B)

The inventors have discovered that the selection of vegetable oil and co-active substance, among other parameters, is connected with technical effects in terms of stability at low temperature, odour, viscosity. In the cosmetic compositions of the invention, preferred combinations of a vegetable oil (A) and a co-active substance (B) include combinations of one or more of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Jojoba oil, Cassia oil, Argan oil, Coconut oil, Rice Bran oil, and Crambe oil, preferably Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Argan oil, Coconut oil, such as:

- Avocado oil and one or more of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and Cs-Ci4 carboxylic acid.

- Avocado oil and one or more of Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride;

- Baobab oil and one or more of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and Cs-Ci4 carboxylic acid, or Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride;

- Guar oil and one or more of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and Cs-Ci4 carboxylic acid, or Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride;

- Amaranthus oil and one or more of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and Cs-Ci4 carboxylic acid, or Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride; - Cassia oil and one or more of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and Cs-Ci4 carboxylic acid, or Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride;

- Argan oil and one or more of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and Cs-Ci4 carboxylic acid, or Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride;

- Coconut oil and one or more of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and Cs-Ci4 carboxylic acid, or Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride;

- Rice bran oil and one or more of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and Cs-Ci4 carboxylic acid, or Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride;

- Crambe oil and one or more of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil and hydrogenated castor oil/dicarboxylic acid copolymer and Cs-Ci4 carboxylic acid, or Sebacic acid and epoxidized triglycerides polyester, sebacic acid and epoxidized jojoba oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/adipic acid copolymer (and) caprylic/capric triglyceride; - Avocado oil and triglycerides or liquid esters, optionally grafted with fatty acids with a length of 6 or 12 carbon atoms, and/or oil based estolides are derived from Lauric acid and epoxidized triglycerides polyester, Lauric acid and epoxidized jojoba oil polyester, Hexanoic acid and epoxidized triglycerides polyester, Hexanoic acid and epoxidized jojoba oil polyester, or Hexanoic acid and epoxidized jojoba oil polyester.

More particularly preferable combinations are, as vegetable oils (A) Avocado oil, Baobab oil, Guar oil, Amaranthus oil, together with one or more of co-active substances (B).

Further ingredients

The aforementioned composition preferably further comprises one or more ingredients, selected from the group, consisting of a pH regulating system, emollient(s), excipient(s), a surfactant system, guar, rheology modifier(s), antioxidant(s), conditioning polymer(s) and solubilization agent(s) as known in the art. The composition can also comprise a chassis as described below.

Preferably, a pH regulating system comprises citric acid.

Sulfated or non-sulfated chassis and surfactant systems

The composition of the invention can include a sulfated or sulfate-free chassis. Suitable chassis are disclosed in US 2012/021025 Al, the content of which is incorporated by reference. Some appropriate structured surfactant systems are described in the following documents: WO9705857, W02000059454, W001019949, WO9932069, W00170926, W00170193, WO0267892,

W003017968, W02005084614, W02002005758, W02005063174,

W02005110355, US20080153730, EP586275, WO03055456, WO03055455, W02006023548, WO2006127394, W020060135627, W02008039440,

US20080233061.

Further preferred chassis compositions are provided below and in the Materials and Methods section.

Emollient

In another embodiment, the composition of the invention may further comprise at least one emollient, preferably a liquid fatty ester other than the coactive ingredient. Non-limiting examples of emollients useful in the invention include ethyl laurate, butyl laurate, hexyl laurate, isohexyl laurate, isopropyl laurate, isoamyl laurate, methyl myristate, ethyl myristate, butyl myristate, isobutyl myristate, isopropyl myristate, 2-octyldodecyl myristate, 2-ethylhexyl monococoate (or octyl monococoate), ethyl palmitate, isopropyl palmitate, isobutyl palmitate, 2-ethylhexyl palmitate (or octyl palmitate), butyl stearate, isopropyl stearate, isobutyl stearate, isocetyl stearate, isostearyl isostearate, isopropyl isostearate, 2-ethylhexyl stearate (or octyl stearate), 2-ethylhexyl hydroxystearate (or octyl hydroxystearate), glyceryl triacetyl hydroxyl stearate, decyl oleate, isononyl isononanoate, tridecyl neopentanoate, isocetyl neopentanoate, isostearyl neopentanoate, octyldodecyl neopentanoate, diisopropyl adipate, dicaprylyl carbonate, pentaerythrityl tetracaprylate/tetracaprate, glyceryl oleate, sodium isostearoyl lactylate, isosorbide dicaprylate and isoarachidyl neopentanoate, and mixtures thereof.

Preferably, the ester is a fatty ester chosen from isoamyl laurate, isopropyl myristate, methyl myristate, ethyl myristate, butyl myristate, isobutyl myristate, 2- octyldodecyl myristate, 2-ethylhexyl monococoate (or octyl monococoate), ethyl palmitate, isopropyl palmitate, isobutyl palmitate, 2-ethylhexyl palmitate (or octyl palmitate), butyl stearate, isopropyl stearate, isobutyl stearate, isocetyl stearate, isostearyl isostearate, isopropyl isostearate, 2-ethylhexyl stearate (or octyl stearate), isononyl isononanoate, 2-ethylhexyl hydroxystearate (or octyl hydroxystearate), glyceryl triacetyl hydroxyl stearate, diisopropyl adipate, dicaprylyl carbonate, pentaerythrityl tetracaprylate/tetracaprate, glyceryl oleate, sodium isostearoyl lactylate, isosorbide dicaprylate and decyl oleate, and mixtures thereof; and more particularly from isopropyl myristate, isononyl isononanoate, isopropyl palmitate, isoamyl laurate, glyceryl triacetyl hydroxyl stearate diisopropyl adipate, dicaprylyl carbonate, pentaerythrityl tetracaprylate/tetracaprate, glyceryl oleate, sodium isostearoyl lactylate, isosorbide dicaprylate and mixtures thereof.

An emollient, if present in the composition of the invention, can advantageously vary from 0.1 to 10%, preferably 0.5 to 5% by weight relative to the total weight of the composition.

Co-surfactant

In another embodiment, the composition of the invention may further comprise at least one co-surfactant preferably a glycol ester of fatty acid or diacid, more preferably a glycol distearate. If present, the total amount of a co-surfactant in the composition of the invention is advantageously varying from 0.1 to 10%, preferably 0.5 to 5% by weight relative to the total weight of the composition.

Emulsifier

In one aspect, the composition of the invention may further comprise at least one emulsifier preferably an alkoxylated fatty acid or derivative thereof.

Advantageously, the emulsifier is a mono- or poly- alkyl or alkenyl ester of an alkoxylated fatty acid, with said fatty acid being a saturated or unsaturated hydroxylated (C8-C22) fatty acid, preferably a unsaturated hydroxylated (C8-C22) fatty acid.

Suitable fatty acids include saturated or unsaturated, hydroxylated or nonhydroxylated, (C8-C22), more typically (C12-C18), fatty acids and combinations thereof.

Typical examples of saturated or unsaturated hydroxylated (C8-C22) fatty acids include ricinoleic acid, lesquerolic acid, hydroxy erucic acid (16- hydroxydocos-cis-13-enoic acid) or hydroxypalmitoleic acid (12-hydroxyhexadec- ci s-9-enoic acid), and combinations thereof.

Emulsifiers which may be incorporated into the composition of the invention may be obtained by esterification of alkoxylated fatty acids, which are commercially available compounds. Such reactions can be implemented by conventional methods which are well known by the skilled person.

Examples of suitable emulsifiers include PEG- 18 CASTOR OIL DIOLEATE, which is an oleic acid diester of ethoxylated castor oil in which the average ethoxylation value is 18, and which is sold for instance under the name Marlowet CG.

Mention may be also made of PEG 16 CO Oleate available under the name Alkamuls PEG 16 CO sold by Syensqo.

Preferably, an emulsifier is present in a concentration ranging from 0.01 to 10% by weight relative to the total weight of the composition, for example from 0.1 to 5 %, for example from 0.2 to 4 %, for example from 0.5 to 3%.

Fatty alcohol

It can be advantageous for the composition according to the invention to further comprise at least one fatty alcohol, preferably C16-C18 linear fatty alcohols. The fatty alcohol can be present in an amount varying from 0.5 to 15%, preferably 1 to 10% by weight relative to the total weight of the composition.

Antioxidant

The cosmetic compositions of the invention can include an antioxidant. Antioxidants act as free radical acceptors and can terminate free radicals at the initiation stage. Preferred antioxidants are hindered phenolics like BHA (Butylated hydroxyanisole), BHT (Butylated hydroxytoluene), TBHQ (tertiary butylhydroquinone), and tocopherols, as well as polyhydroxy phenolics like propylgallate are primary antioxidants, which delay or inhibit the initiation step by reacting with a lipid free radical or by inhibiting the propagation step by reacting with the peroxy or alkoxy radicals. Thus, suitable antioxidants include, but are not limited to, phenolic substances, butylated hydroxyanisole, butylated hydroxytoluene, tertiary butylhydroquinone, tocopherols, polyhydroxy phenolics, and propyl gallate.

The anti oxi dant(s) may be present in an amount of 0 to 10% by weight, preferably 0 to 1% by weight more preferably 0,1 to 0,9% by weight, even more preferably 0,1 to 0,5% by weight, based on the total mass of the composition.

Other ingredients

In addition to the compounds indicated above, a composition according to the invention can comprise a physiologically acceptable medium.

A physiologically acceptable medium is a medium which is particularly suitable for the application of a composition of the invention to the hair. The physiologically acceptable medium is generally suited to the nature of the substrate to which the composition must be applied, and also to the way in which the composition must be packaged.

Preferably, the composition of the present invention comprises water in an amount of from 5 to 90 % by weight relative to the total weight of the composition.

It may comprise for instance at least 25 %, for instance at least 50 %, for instance at least 60 % of water, relative to the total weight of the composition.

In one embodiment, the cosmetically acceptable aqueous medium can be composed solely of water. For example, the composition of the invention may further comprise at least one water-miscible organic solvent.

According to this embodiment, the cosmetically acceptable aqueous medium can be composed of a mixture of water and of a cosmetically acceptable solvent, such as a lower C1-C4 alcohols or such as alkylene glycols. The lower C1-C4 alcohols are preferably chosen from ethanol, isopropanol, tert-butanol, and n- butanol. The alkylene glycols are preferably chosen from propylene glycol and glycol ethers.

The composition of the invention may further comprise additional optional ingredients which may bring specific benefits for the intended use. Such optional ingredients may include colorants, pearlescent agents, emollients, hydrating agents, preservatives and pH adjusters. The skilled person is able to select according to general knowledge in the art of formulating shampoos and conditioners, and the vast literature there-related, appropriate such optional ingredients for application purposes.

The composition of the present invention may further comprise from about 0.1 to about 50 % by weight, more typically from about 0.3 to about 25 % by weight, and still more typically from about 0.5 to 10 % by weight, of one or more benefit agents.

The composition according to the present invention may optionally further comprise other ingredients common in cosmetic formulations, such as, for example, preservatives such as benzyl alcohol, methyl paraben, propyl paraben, imidazolidinyl urea, sodium benzoate, potassium sorbate, salicylic acid, methylchloroisothiazolinone and methylisothiazolinone, thickeners such as high molecular weight crosslinked polyacrylic acid (carbomer), PEG diester of stearic acid and the like, and viscosity modifiers such as block polymers of ethylene oxide and propylene oxide, electrolytes, such as sodium chloride, sodium sulfate, and polyvinyl alcohol, pH adjusting agents such as citric acid, succinic acid, phosphoric acid, sodium hydroxide, and sodium carbonate, perfumes, dyes, and sequestering agents, such as disodium ethylenediamine tetra-acetate. In general, hair care compositions may optionally comprise, based on 100 % by weight of the personal care composition and independently for each such ingredient, up to about 10%, preferably from 0.5 % to about 5.0 %, of such other ingredients, depending on the desired properties of the hair care composition.

In one specific embodiment, the composition according to the present invention further comprises a fragrance material or perfume.

As used herein, the term “fragrance material or perfume” means any organic substance or composition which has a desired olfactory property and is essentially non-toxic. Such substances or compositions include all fragrance material and perfumes that are commonly used in perfumery or personal care compositions. The compounds involved may be natural, semi-synthetic or synthetic in origin. In one embodiment, the composition comprises from 0.01 to 10 % by weight of the fragrance material or perfume based on the total weight of the composition. In another embodiment, the composition comprises from 0.1 to 5 % by weight of the fragrance material or perfume based on the total weight of the composition. In still another embodiment, the composition comprises from 0.2 to 2 % by weight of the fragrance material or perfume based on the total weight of the composition.

A hair care composition provided by the present invention is used in a manner known in the art, for example by application of the composition to the hair and optionally rinsing the composition off of the hair with water.

Preferably, the composition of the invention may have a pH comprised between 4 and 11, for instance between 4 and 6.

The composition of the invention may also take the form of concentrates that are suitable to prepare a haircare product.

Concentrates including a mixture of surfactants and/or conditioning agents and/or solubilizer are advantageous as their use would reduce the need to transport a plurality of individual components.

Personal care compositions are usually prepared by mixing individual surfactants, solubilizers and conditioning agents. These components may be supplied as concentrated solutions which are diluted and/or and combined in appropriate ratios by the formulator.

Preferably, a composition of the invention may further comprise a thickener.

Preferably, a composition of the invention may comprise less than 5 % by weight of an additional thickener.

In particular, a composition of the invention may comprise less than 5 % by weight of polymeric thickener(s), relative to the total weight of composition, for instance less than 3 % by weight, for instance less than 2 % by weight, for instance less than 1 % by weight.

According to one embodiment, a composition of the invention may comprise substantially no polymeric thickener, i.e. from 0 to less than 0.1 % by weight of polymeric thickener per 100 % by weight of the composition, for instance no polymeric thickener, i.e. 0 % by weight of polymeric thickener per 100 % by weight of the composition.

To thicken and stabilize compositions containing vegetable oils, stabilizers such as crosslinked acrylic polymers of the Carbopol type are frequently used. However, these stabilizers can have the drawback of reducing the cosmetic performance. For instance, in the case of shampoos, using such synthetic polymers makes the hair more laden (charged or loaded) and coarser.

Preferably, a composition of the invention may comprise less than 5 % by weight of one crosslinked copolymer.

A particularly preferable formulation according to the invention comprises the following:

A further example for a cosmetic formulation in the form of an emulsion is as follows:

The above formulation is particularly suitable for conditioner, mask, serum, combing cream, cowash, lotion, or a prewash.

Method for preparing chemically modified oils

Preferably, step (i) is carried out by the reaction between triglyceride and glycerin, in stoichiometry for the majority formation of di glycerides, such that monoglycerides will be formed in smaller quantities, using lipases as a catalyst. In step (i), any of the vegetable oils described herein, which is mostly comprised of triglyerides, is treated with glycerin in a glycerolysis using a lipase as a catalyst. In step (ii), the vegetable oil(s) subjected to glycerolysis is esterified with a dicarboxylic acid. Suitable dicarboxylic acids are selected from dicarboxylic acids of the general formula:

HOOC-Y-COOH wherein Y is preferably a saturated or unsaturated alkyl chain, or Y is an aromatic residue. For example, Y can be a divalent 1,2- 1,3 or 1,4-phenyl residue. More preferably, the dicarboxylic acid is of the general formula

HOOC-(CH₂)n-COOH, i.e. Y is -(CFbjn- wherein n is preferably 1-20 or 1-10, more preferably, n is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Particularly preferred dicarboxylic acids are oxalic acid (ethanedioic acid), malonic acid (propanedioic acid), Succinic acid (butanedioic acid), Glutaric acid (pentanedioic acid), adipic acid (hexanedioic acid), pimelic acid (heptanedioic acid), suberic acid (octanedioic acid), azelaic acid (nonanedioic acid), sebacic acid (decanedioic acid), phthalic acid (benzene- 1,2-dicarboxylic acid), orthophthalic acid, isophthalic acid (benzene- 1,3 -dicarboxylic acid), metaphthalic acid, terephthalic acid, and para-phthalic acid.

Preferably, in the aforementioned method, the vegetable oil subjected to step (i) is selected from the group, consisting of Coconut oil, Babassu oil, Crambe oil, Pequi oil, Mango oil, Grape oil, Maracuja oil, Pumpkin Seed oil and Pracaxi oil, and/or the dicarboxylic acid is selected from the group, consisting of adipic acid and sebacic acid.

Preferably, the lipase used in step (i) is commercially available lipase as supplied from Novozymes, for example NZ 435™ or Lipura Flex™. A typical lipase loading is about 3-8% by mass or 3-6% by mass. For example, lipase loading is 4,5% by mass.

In the glycerolysis step (i), a suitable ratio of glycerine to vegetable oil is 2: 1 or 3: 1 in terms of moles. Preferably, 1 mol of vegetable oil (triglyceride) is reacted with 2 mol of glycerin.

During the esterification step (ii), the temperature is preferably increased. A generally preferable increased temperature range for step (ii) is 150-250°C, preferably 170-200°C. A suitable temperature increase rate is 5°C/h, preferably 10°C/h, more preferably 15°C/h. Preferably, in the method of the invention, the product of step (i) is not isolated for step (ii), but is used as obtained from step 1, with the mixture of mono- and diglycerides to start step (ii) of esterification with the chosen diacid.

In an exemplary method, the vegetable oil, 14 part of glycerine, and lipase is loaded in a glass reactor, and homogenized using mechanical agitation. The proportion considered between triglyceride and total glycerin for the glycerolysis reaction, predicting higher final levels of diglyceride, will be 1 mol of triglyceride for 2 mol of glycerin. The temperature increases to 65-70oC, Nitrogen is adopted to the inert atmosphere. The monoglyceride, diglyceride contents and hydroxyl index will be controlled to complete the glycerolysis reaction.

Exemplary process for step (ii) - Esterification

The product of stage 1 is loaded in a glass reactor, the dicarboxylic acid added homogenized using mechanical agitation, Nitrogen is adopted to inert atmosphere. The temperature is increased to 150-230°C, preferably 170°C to 200°C with a temperature increase rate of 10°C per hour. The reaction is accompanied by a reduction in the acid number.

An exemplary process can be summarized as follows:

Step (i)- Glycerolysis

For example, as the main products, di glyceryl esters and monoglyceryl esters can be obtained according to the following schemes: a) formation of diglyceryl ester

J" triglyceride (oil) [' glycerine b) formation of monoglyceryl ester (example):

The molecules represent an oleic acid triglyceride (generic oil), tri glyceryl oleate, however it should be noted that the above example is a generic representation, the fatty acids in the structure of the triglyceride and subsequently in the structure of the diglyceride and monoglyceride products will be those derived from the oil used in the reaction, which can be, for example, from C8 to C22 or higher, and can be saturated, unsaturated and polyunsaturated chains.

In step (ii), the mixture of monoglyceride and diglyceride will react with a dicarboxylic acid, in the case of the example adipic acid is chosen for the reaction, forming the esters that will be the final products. This reaction step can be carried out using chemical, enzymatic catalysts or the absence of catalysts, just using heating to achieve the activation energy necessary for esterification.

As an example, the transformations for adipic acid and a diglyceryl ester are described below:

Adipate Diglyceryl Ester adipate diglyceryl ester and

- Adipate Monoglyceryl Ester and

Adipate Monoglyceryl Diglyceryl Ester diglyceryl noglyceryl Adipate Ester

The polymerization of the diacid is possible, forming other molecules in addition to the main ones.

The present invention also provides a chemically modified vegetable oil obtained by the aforementioned process.

Use applications

The cosmetic compositions of the invention can be used in different cosmetic applications, in particular haircare and skincare.

In particular, the compositions of the invention can be preferably used in hair conditioning compositions, preferably wherein said use is for increasing hair hydrophobicity, composition which can be formulated as a suspension (e.g., a liposomal suspension), emulsion, nano-emulsion, hydrogel, multiphase solution, liposomal dispersion, lotion, cream, gel, essence, foam, liquid, cake, ointment, paste, serum, spray, aerosol, conditioner, shampoo, mask, cleanser, tonic, makeup (e.g., lipstick, foundation, bronzer, rouge, eyeshadow), patch, pencil, powder, towelette, soap, cleanser, stick, mousse, elixir, concentrate and/or after-shave.

A skincare composition can be formulated within a wide range of pH levels. In one embodiment, the pH of the topical composition ranges from 1.0 to 13.0. In some embodiments, the pH of the topical composition ranges from 2.0 to 12.0. Other pH ranges suitable for the subject composition include from 3.5 to 7.0, or from 7.0 to 10.5. Suitable pH adjusters such as sodium hydroxide, citric acid and triethanolamine may be added to bring the pH within the desired range. Preferably, a cosmetic skincare composition may comprise additional cosmetic ingredients. These components may be considered active ingredients or inactive ingredients, and can be categorized by the benefit they provide or by their postulated mode of action; however, it is to be understood that the additional components can in some instances provide more than one benefit or operate via more than one mode of action. Therefore, classifications herein are made for the sake of convenience and are not intended to limit the agent to that particular application or applications listed.

Examples of such cosmetic ingredient classes include: organic solvents, silicones, pH adjusters, chelating agents, gelling agents, proteins, vitamins, emollients, oils, hydroxy acids, exfoliants, retinoids, viscosity modifiers, polymers, minerals, insect repellents, lubricants, preservatives, botanicals, clarifying agents, humectants, non-biological surfactants, antioxidants, thickeners, softeners, sunscreens, moisturizers, dyes, colorants, fragrances, abrasives, absorbents, aesthetic components such as essential oils, skin sensates, astringents, anti-acne agents, anti-caking agents, antifoaming agents, antimicrobial agents, depigmenting agents, anti-inflammatory agents, advanced glycation end-product (AGE) inhibitors, steroids, binders, biological additives, buffering agents, bulking agents, chelating agents, chemical additives, denaturants, external analgesics, keratolytic agents, desquamating agents, keratinocyte proliferation enhancers, collagenase inhibitors, elastase inhibitors, film formers or materials, opacifying agents, propellants, reducing agents, enzymes, sequestrants, skin bleaching and lightening agents, skin-conditioning agents, skin soothing and/or healing agents, thickeners, minerals, vitamins and derivatives thereof.

For example, the compositions of the present invention can be used in personal care products. For example, the compositions can be used by applying the cosmetic composition to an area of skin on a body; washing the area of skin on the body; and rinsing the area of skin on the body.

For example, a topical cosmetic composition can be formulated as, for example, a suspension, emulsion, nanoemulsion, hydrogel, multiphase solution, liposomal dispersion, lotion, cream, gel, foam, ointment, paste, spray, conditioner, shampoo, mask, cleanser, micellar water, tonic, makeup (e.g., lipstick, foundation, bronzer, rouge, eyeshadow), and/or after-shave. For example, the cosmetic composition of the invention can be used for improving the health and/or appearance of skin wherein a topical cosmetic composition is applied directly to an area of the subject’s skin in need thereof.

Moreover, the compositions of the invention are preferably used in hair conditioning compositions, preferably wherein said use is for increasing hair hydrophobicity.

As explained above, the compositions of the invention are effective in haircare. For example, the compositions are effective in hydrophobicizing the hair. For example, the cosmetic composition of the invention is useful in haircare products such as shampoo or conditioning products. Namely, using compositions of the invention, hair fibers treated with the mixtures become more hydrophobic in comparison with the fibers treated with individual components. There are also indications that the deposition of oil on the fibers is facilitated by the presence of co-active. This effect of the two actives with respect to their surface properties (more pronounced hydrophobicity) correlated with improved performance in sensorial tests. Also, it is possible to use the haircare compositions provided by the invention for improved surface properties. The mixture of a vegetable oil and a coactive substance can also be used as silicone oil free alternatives for hair conditioners in hair care products.

Moreover, the compositions of the present invention are useful for skincare applications, such as emollient compositions, skin moisturizing compositions and other skincare applications such as skin masks, anti-ageing applications and similar applications.

EXAMPLES

Example 1

Synthesis of Diglycerides

Two different compositions can be achieved using different methods to obtain higher levels of diglycerides from triglycerides using enzymes as catalysts. It is possible to obtain a mixture of diglycerides, monoglycerides and fatty acids removed from the triglyceride structure through the enzymatic hydrolysis procedure, or monoglycerides and diglycerides without the presence of free fatty acid, by glycerolysis reaction also using lipases as catalysts in the process.

1) Enzymatic Hydrolysis In this process, diglycerides are obtained in greater content and the fatty acids remain free in the mixture of final components.

Raw Material List:

1) Vegetable oil with triglyceride content, e.g. Coconut Oil, Babassu Oil, Crambe Oil, Pequi Oil, Mango Oil, Grape Oil, Maracuja Oil, Pumpkin Seed Oil or Pracaxi Oil.

2) Vegetable Glycerin

3) Lipase, e.g. NZ 435 or Lipura Flex enzyme (lipase B from Candida Antarctica), supplied by Novozymes

Synthesis Method

The triglyceride water and lipase are loaded in a glass reactor;

The reactor is heating using water to 65-70°C of temperature;

- Mechanical agitation is adopted for homogenization;

The hydrolysis procedure continues until the acid index is equivalent to 1/3 of the oil's saponification index.

Exemplary reaction scheme (generalized structures):

Other examples:

Partial hydrolysis of Mango Oil, Babassu Oil and Crambe Oil for high diglyceride content using lipases as hydrolysis catalysts. Raw Material: Triglycerides (Mango, Babassu or Crambe Oil), Lipases CALB - lipase B, Candida antarctica. TL100 L - lipase originating from Thermomyces lanuginosus Novozymes supplier, water.

Protocol: The triglyceride, water and enzyme mixture are loaded into a glass reactor, heated to 65-70°C, mechanical stirring. The acid value is monitored until it represents the equivalent of the diglyceride content predicted by the oil's Saponification Index. The agitation is stopped, the aqueous phase is drained and the mixture of diglycerides and fatty acids is dried at 120°C under vacuum. An average reaction time can be 6-12 hours. for mango oil:

Palmitic Acid (C16:0) 6 - 13% Stearic Acid (Cl 8:0) 37 - 42% Oleic Acid (Cl 8: 1) 38 - 45% Linoleic Acid (Cl 8:2) 5 - 8% Linolenic Acid (C18:3) 0,3 - 5% Gadoleic acid (C20: l) 0 - 2,5% Behenic Acid (C22:0) 0,3 - 1,3%

Oil Saponification Index 190 mg KOH/g

Technical specification of Mango Diester:

Acidity Index 55 - 75 mg KOH/g Saponification Index 180 - 215 mg KOH/g

Hydroxyl Index 40 - 60 mg KOH/g

Typical Composition for Babassu Oil Caprylic Acid (C8:0) 2,6 - 7,3% Capric Acid (C10:0) 1,2 - 7,6% Lauric Acid (C12:0) 40,0 - 55,0 % Myristic Acid (C14:0) 11,0 - 27,0% Palmitic Acid (C16:0) 5,2 - 11,0% Stearic Acid (C18:0) 1,8 - 7,4% Oleic Acid (Cl 8: 1) 9,0 - 20,0% Linoleic Acid (Cl 8:2) 1,4 - 6,6%

Oil Saponification Index 251,0mg KOH/g

Technical Specification of Babassu Diester:

Acidity Index 75 - 105 mg KOH/g Saponification Index 240 - 260 mg KOH/g

Hydroxyl Index 80 - 110 mg KOH/g

Typical Composition for Crambe Oil

Palmitic Acid (Cl 6:0) 3,4%

Stearic Acid (C18:0) 11%

Oleic Acid (C18:l) 17,8%

Linoleic Acid (C18:2) 6,1%

Linolenic Acid (C18:3) 2,8%

Arachidic Acid (C20): 1,7%

Eicosenoic Acid (C20: l) 6,7%

Behenic Acid (C22): 3,7 %

Erucic Acid (C22:l) 56,7%

Oil Saponification Index 171 mg KOH/g

Technical Specification of Crambe Diester

Acidity Index 55 - 95 mg KOH/g

Saponification Index 150 - 190 mg KOH/g

Hydroxyl Index 25 - 65 mg KOH/g

2) Enzymatic Glycerolysis

This procedure consists of obtaining a high content of diglycerides from the reaction of triglyceride with glycerin, using lipases as catalysts, the fatty acids removed from the triglyceride structure will be esterified with glycerin, generating the final product with a low acidity index. An average reaction time can be 6-12 hours.

Raw Material List:

2) Lipases (e.g. NZ 435, Lipura Flex (lipases B from Candida antarctica), supplied by Novozymes)

3) vegetable glycerin

Synthesis Method

The triglyceride, 1/4- 1/2 part of glycerin by mole, and the lipase is loaded in a glass reactor, homogenized using mechanical agitation. The amount of glycerin is divided into 4 parts which is added consecutively to the reaction. The temperature increases to 65-70°C, and mechanical stirring is performed for homogenization and reaction. The remainder of the glycerin is added every 12 hours. Once the addition of glycerin is complete, the acid number is analyzed and the reaction continues until the Acid Number is below 1.0 mg KOH/g.

Below is a generic representation of formulas representing an oleic acid triglyceride (generic oil), tri glyceryl oleate:

Further example:

Glycerolysis of Mango Oil to greater yield of diglyceride, low fatty acid free content using lipase NZ435 as a catalyst.

Analysis results obtained after complete glycerolysis procedure:

Acid Index (IA) 0,28 mg KOH/g, Alcohol Index (IOH) 154,68 mg KOH/g, Monoglycerides 20,6%, Diglycerides 79%, Free Glycerol 1,16%, Peroxides 3,9%

Example 2.

Chemical enzymatic transformation As described above, chemical-enzymatic transformation involving two reaction stages was used. In the first step, different vegetable oils will react with glycerin, in a glycerolysis process, to form diglycerides and monoglycerides. In a second step they are esterified with a dicarboxylic acid such as adipic or sebacic acid.

Raw Material List:

1) Vegetable oil with triglyceride content, e.g. Coconut Oil, Babassu Oil, Crambe

Oil, - Pequi Oil, Mango Oil, Grape Oil, Maracuja Oil, Pumpkin Seed Oil or Pracaxi Oil.

2) Vegetable Glycerine

3) Dicarboxylic Acids as a Adipic Acid, Sebacic Acid (step 2)

4) Lipases: NZ 435 or Lipura Flex enzyme, supplied by Novozymes

Step 1 - Glycerolysis

The triglyceride, 1/4-1/2 part of glycerine by mole, and the lipase is loaded in a glass reactor, homogenized using mechanical agitation. The amount of glycerin is added in 4 parts to the reaction. The temperature increases to 65-70°C, Nitrogen is adopted to generate an inert atmosphere. The monoglyceride, diglyceride contents and hydroxyl index are controlled to complete the glycerolysis reaction. Preferably, the reaction times are: 1st, 2nd and 3rd stage - 4 to 8 hours of reaction after adding glycerin, preferably 6 hours, 4th stage - 12 -18 hours of reaction after adding glycerin, preferably 14 hours.

Step 2 - Esterification

The product of stage 1 is loaded in a glass reactor, the dicarboxylic acid added homogenized using mechanical agitation, nitrogen is adopted to maintain an inert atmosphere. The temperature is increased to 170°C to 200°C, increasing at a rate of 10°C per hour. The reaction is accompanied by a reduction in the acid number to values below 1.0 mg KOH/g. Preferably, the reaction time for the esterification step is 6 to 12 hours, more preferably 8 hours.

Analytical Results were as follows (measurement details are indicated in the Materials and Methods section):

Typical composition of Pracaxi Oil

Caproic Acid 0 - 0,2%

Lauric Acid 0 - 0,2%

Myristic Acid 0 - 0,1% Palmitic Acid 1,4 - 1,5% Stearic Acid 2,5 - 2,5% Oleic Acid 46 - 54% Linoleic Acid 12 - 13% Linolenic Acid 0,1 - 1,4% Arachidic Acid 0 - 12% Behenic Acid 11-23 % Lignoceric Acid 0,3 - 1,3 %

Analytical Results: Step 1 Step 2

IOH 196 mg KOH/g IA 0,6 mg KOH/g 31% Monoglyceride Hydroxyl Index 48,9 mg KOH/g 70% diglyceride Saponification Index 188,6 mg KOH/g

Refraction Index (25°C) 1,4725

Viscosity (40°C, cSt) 53,6 Synthesis of compounds

Example 3-1) Epoxidation of unsaturated triglyceride

The reaction was conducted under an inert nitrogen atmosphere. In a threenecked round-bottom flask of 250 mL, equipped with a magnetic stirrer, a condenser, a thermal probe, and a magnetic stirrer, 90 g of avocado oil (0.104 mol), 11.86 g of acetic acid (0.207 mol) and 32.29 g of Amberlite 120H IR were introduced. The mixture was stirred and heated to 75 °C with an oil bath. When the temperature reached 75 °C, 35 mL of an aqueous solution of H2O230% was slowly added into the mixture using a syringe driver over one hour while maintaining the temperature at 75 °C. At the end of the introduction, the temperature was increased to 85 °C and the mixture was stirred for five hours. After five hours, the mixture was allowed to cool down to 60 °C, and then 50 mL of chloroform was added to the mixture. After 5 minutes under stirring, the mixture has been filtered to remove Amberlite 120H IR and transferred into a separating funnel. The organic phase was recovered after two washing with water, drying with MgSO4, and elimination of chloroform under reduced pressure. 70 g of a yellow oil was obtained.

The complete conversion was confirmed by ¹ H NMR.

Example 3-2) Esterification of epoxidized triglyceride with a fatty acid. The reaction was conducted under an inert nitrogen atmosphere. In a three-neck round-bottom flask of 250 ml, equipped with a magnetic stirrer, a condenser, a dropping funnel and a temperature probe were added 37.94 g of Dodecanoic acid (0.189 mol). The mixture was heated at 150 °C and 50 g of Epoxidized Rice Bran oil (0.054 mol) were added with the dropping funnel over lh30. When the introduction was completed, the mixture was stirred at 150 °C for lh30. The mixture was allowed to cool down at room temperature to recover the final product as a yellowish grease solid.

The conversion of epoxy groups into esters (85 %) was determined by 'H NMR

Example 3-3) Esterification of epoxidized triglyceride with sebacic acid

The reaction was conducted under an inert nitrogen atmosphere. In a three-neck round-bottom flask of 250 ml, equipped with a magnetic stirrer, a condenser, a dropping funnel and a temperature probe were added 15.73 g of sebacic acid (0.078 mol). The mixture was heated at 150 °C and 45 g of epoxidized Avocado oil (0.052 mol) were added with the dropping funnel over lh30. When the introduction was completed, the mixture was stirred at 150 °C for lh30. The mixture was allowed to cool down at room temperature to recover the final product as a yellowish grease solid.

The conversion of epoxy groups into esters (> 95 %) was determined by ^JH NMR

Example 3-4) Esterification of epoxidized jojoba oil with sebacic acid

The reaction was conducted under an inert nitrogen atmosphere. In a three-neck round-bottom flask of 250 ml, equipped with a magnetic stirrer, a condenser, a dropping funnel and a temperature probe were added 9.74 g of sebacic acid (0.058 mol). The mixture was heated at 150 °C and 30 g of Epoxidized Jojoba oil (0.049 mol) were added with the dropping funnel over lh30. When the introduction was completed, the mixture was stirred at 150 °C for lh30. The mixture was allowed to cool down at room temperature to recover the final product as a yellowish grease solid.

The conversion of epoxy groups into esters (> 95 %) was determined by ^JH NMR.

4 Contact angle measurement

As described in the Materials and Methods section, the contact angle was measured as an indication of the degree of hydrophobicity. Different formulations of vegetable oil (A) and co-active substance (B) were tested to measure the contact angle. The measurement was performed as indicated in the Material and Methods section. Figure 1 shows the results. Thus, the hydrophobicity is improved with the specific combination of vegetable oil (A) and co-active substance (B) according to the invention. This parameter makes it possible to determine the condition of the hair and also to observe whether there is a deposit of active ingredients.

A comparison with silicone oil containing preparations was made in sensorial panels, as described in the Materials and Methods section.

The following abbreviations are used (see also Materials and Methods section): DV920: Hydrogenated castor oil and hydrogenated castor oil/adipic acid copolymer and caprylic/capric triglyceride (available from Syensqo).

The results show that the cosmetic composition of the invention has a strong potential for effective cosmetic composition in particular in hair conditioning, and also as silicone oil-free products in hair care products.

MATERIALS AND METHODS

The current section is structured in the following manner. Section 1 presents information on the components used in the examples. That includes the actives of interest (with potential conditioning action) and the surfactants or other components employed in the surfactant chassis of a particular active. In section 2, the experimental protocols are described, employed to prepare the formulations, perform the in vitro (wet and dry combing) and in vivo evaluations.

1. Materials.

Table 2 presents the composition of surfactant chassis of the formulation used in the examples.

Table 1. Components used to prepare the formulations. Table 2. Composition of surfactant chassis of the formulation, oil-infused shampoo.

2. Methods

The current section is organized in the following manner. Section 2.1 presents the protocols for the preparation of the studied formulation. Section 2.2 explains the protocol for production of home bleached tresses, starting from virgin tresses. In sections 2.3-2.5 the protocols for characterization of the formulation are described: transmittance, viscosity and stability, respectively. In sections 2.6 and 2.7, the procedure for evaluation of the systems is described in combing test - wet and dry mode, respectively. Section 2.8 presents the procedure, used for evaluation of the humidity of the tresses. In 2.8, the protocol for measurement of contact angle of water on hair fibers is described, and section 2.10 explains how the deposit of active on the hair fiber is quantified. Finally in section 2.11, it is explained how the products are evaluated in sensorial panels.

2.1. Protocol for preparation of the formulation.

The procedure for the preparation of shampoo formulation is as follows.

The 2 blends (Oil blend and Surfactant thickening blend) were prepared during the main formulation stirring time and added to the main formulation accordingly.

Oil blend

• In a beaker, mix pure oil, antioxidant (Tocopherol) and solubilizer (Alkamuls PEG 16CO), and ensure a transparent premix. Heat the premix if needed, then cool down under gentle stirring.

Surfactant thickening blend

• In another beaker at 65 °C, heat Cocamide MIPA (Mackamide CPA) with water under stirring for 5 to 10 minutes, until homogeneous.

• Add Sodium Lauryl Sulphate (Rhodapon LS94 RPB) and then PEG- 150 Distearate (Alkamuls S6000), ensuring homogeneity after each addition. When homogeneous, stop heating and let the mixture stir until it comes back to 25-30 °C.

• Add the required amount of water to fill the water loss during the heating step and re-homogenize.

Main Formulation

• In the main tank, disperse guar (Jaguar® Cl 62) in water at a high stirring speed of 300 rpm and add 0.05 parts of 50% citric acid solution.

• Add Cocamidopropyl Hydroxysultaine (Mackam CBS 50G) and mix for 15 minutes at 100 rpm.

• Add Sodium Laureth Sulfate (Rhodapex ESB) and mix for 30 minutes.

• Add the oil blend under high stirring of 300 rpm for 10 minutes, then reduce the speed to 100 rpm and continue mixing for 15 minutes.

• Add preservatives (Microcare SB) and mix for 20 minutes.

• Add the surfactant thickening blend and stir for 50 minutes at 100 rpm.

• Adjust the pH to 5 with citric acid solution. • Add a minimal amount of salt (NaCl) if needed, to achieve a higher/targeted viscosity.

• Lastly, add the remaining parts with water and a final check/adjustment of pH 4.9 to 5.

2.2. Preparation of bleached tresses.

In the majority of the in vitro experiments, Caucasian tresses are used, Damaged, Level 2. These tresses are mass produced and suitable for experiments like wet combing. However, for the evaluation of the effect of the actives on the wettability of the hair fibers, home bleached tress is needed. Preliminary tests show that the variation of the results (contact angle) with home bleached tresses is significantly lower compared to commercially available tresses. The procedure for bleaching of virgin hair tresses is described below.

Tresses: 25 of 4 g virgin medium brown DA 450 163 8300

Commercial products for bleaching:

■ « Oxydant creme 30% volume », L’Oreal Professionnel Paris lot 44H304

■ « Poudre decol orante Plastifiz Precision », L’Oreal Professionnel Paris lot 44J200

Equipment:

1 Beak in PET capacity 600 ml

1 Tripour beak capacity 400 ml

1 Small Plastic spatula

1 Special hair bleached brush

2 Aluminium sheets

1 red bulk filled up hot water

2 sinks available to rinse

Protocol:

1. Prepare the mixture based on following: niMixTURE (/g of hair) =4.75g weigh first powder with a mask and premix with a spatula and use the add oxidant cream on top in a 600ml mixer when adding water slowly in 4 beak minutes.

2. Drop half of the mixture on aluminium sheet and spread with the special hair bleached-brush

3. Start the timer

4. Deposit the tresses and put the last part of mixture on tresses and spread with the brush

5. First step: mass fast each tress with the mixture (15s/tress). Insist on roots and tips.

6. Second step: mass again each strand more deeply (25s/tress from the top to the bottom). The application time must not exceed 20 min to stay significantly lower than the exposition time.

7. Let them stand until 180 minutes elapsed well covered by a aluminum sheet.

8. Stop oxidation: remove a big part of bleaching cream and dip all the tresses in the same bulk of water to remove at least all of the bleaching product (less than one minute)

9. Rinsing step.

2.3. Measurement of the optical transmittance of the studied systems.

The transmittance of the formulations and the oils was measured via the following procedure. (1) Fill % of the cuvette (over the line) with a formulation sample.

(2) Ensure the formulation does not contain any air bubbles and remove any dust on the cuvette, for an accurate measurement. If the sample is viscous and air bubbles are present, allow the formulation to rest in the cuvette for at least 6 hours or overnight before measurement.

(3) Select the wavelength programmed - Lambda 40Bio Shampoo Transparency at 600 nm.

(4) Calibrate the spectrophotometer’s transparency of 99 to 100% with DI water as the reference.

(5) Place the sample cuvette into the spectrometer, with the clear sides of the cuvette parallel to the light source/monochromator and detector.

(6) Close the lid and run the transmittance measurement.

2.4. Measurement of the viscosity of the studied systems.

The viscosity of the formulations was measured via the following procedure.

• Formulation is filled (90%) into a 100 mL glass bottle.

• Attach the selected spindle to the Brookfield instrument and place the spindle into the glass bottle of formulation.

• Run the selected program for 1 minute for viscosity measurement.

• For high accuracy/effective measurement:

- Keep the spindle in the center of the bottle

- Ensure the spindle does not touch the bottom and the wall of the bottle

The midline of the spindle is fully submerged in the formulation

- Ensure that the selected spindle and speed (rpm) provides a good range of viscosity (e.g.: spindle 4 and 10 rpm read a max of 20 000 cP)

Torque percentage between 10 to 100%

The viscosity of the vegetable oils was measured via the following procedure.

• Pure oil is filled (60%) into a 400 mL plastic beaker.

• Attach spindle 1 to the Brookfield machine and place the spindle into the plastic beaker of oil.

• Run the program of spindle 1 at 5 rpm for 1 minute.

• For high accuracy/effective measurement:

- Keep the spindle in the center of the bottle - Ensure the spindle does not touch the bottom and the wall of the bottle

The midline of the spindle is fully submerged in the formulation

- Ensure selected spindle and speed (rpm) provides a good range of viscosity (e.g.: Spindle 4 and 10 rpm read a max of 20 000 cP) Torque percentage between 10 to 100%

2.5. Tests of the storage stability of the formulation.

The samples were put into glass bottles of 100 ml and stored at three different temperatures: 4 °C, room temperature, 40 °C. On a monthly basis the samples, stored at 4/40 °C, is taken out of the fridge/climate chamber, thermo stated for 24 hours and their transmittance, pH and viscosity are measured.

2.6. Procedure for wet combing and data interpretation.

The wet combing was performed via a combing instrument, produced by Diastron. Tresses of Caucasian hair were used, damaged level 2, 4 grams, length 17 mm.

The hair of the tress is held together by a plastic part, which is attached to the (force) sensor of the instrument. The comb moves down the tress at a constant speed (300 mm/min). The comb has relatively wide teeth (6.9 teeth per centimeter). During this movement the instrument records the force exerted on the sensor. Typical result (force vs. distance) is presented in Figure 2.

The results presented in Figure 2 can be processed to quantify the softness of the tress, and therefore the effectiveness of the active as a conditioning agent. The following parameters can be utilized:

• Force in the plateau, Fp.

• Thermodynamic work for combing in the plateau, PFp.

• Thermodynamic work for combing for the entire pass of the comb, W.

• Maximum force, FM.

The force and the work for combing are a function of the following properties/parameters (at the same speed):

• Distance between the teeth of the comb. The narrower the teeth are the greater the resistance is to the motion of the comb. When comparing a range of systems one needs to use the same comb.

• Inherent softness of the tress, all of the experiments were performed with the same type of tress (Caucasian hair, damaged level 2, 4 g). The quality and properties of these tresses is to a significant extend standardized. However, the inherent softness of the tresses (before treatment with shampoo) can vary significantly.

• Effectiveness of the conditioning active, deposited on the tress. The conditioning active deposited on the hair can change the softness, which results in lower resistance of the tress to the combing.

One of the ways to compare the softness of different systems is to compare the total work for combing, W. The lower this value is, the more efficient the respective active is in bringing conditioning to the hair. However, W does not account for the inherent softness of the tress. The efficiency of the active should be judged by the change in the softness of the tress (before and after treatment with the active), and not by the absolute value of the thermodynamic work. That is why in the current description, the parameter W is scaled in the following manner:

WDL = [(PFBEFORE-PFAFTER)/PFBEFORE] X 100 (1)

The parameters in the equation above have the following meaning:

• PFBEFORE - work for combing of the tress after pretreatment (see text below for explanation).

• PFAFTER - work for combing of the tress after treatment with formulation (see text below for explanation).

• PPDL - reduction of the work for combing, as a result of the treatment with shampoo, scaled with the initial work for combing. The multiplication by 100 is done in order to present the results in percent.

In this representation the higher the value of WDL is, the more efficient the respective active is. It is also possible to use the difference (PFAFTER - P BEFORE), which by default is negative. In this case, the lower this number is, the more efficient the active is. The practical procedure on how to perform the wet combing test is presented below.

The procedure consists of three steps: (1) Tress pre-treatment; (2) Treatment of the tress with shampoo; (3) Combing test. Below each of these steps are described.

(1) Pretreatment of the tress.

• Wash for 1 minute the tress with water with temperature 36-37 °C (water temperature is automatically regulated). Water volume rate 60-70 ml/second. • Add 2 ml solution of 14 wt. % SLES to the tress.

• Massage for 1 minute.

• Rinse for 1 minute.

• Add solution 2 ml of 14 wt. % SLES to the tress.

• Massage for 1 minute.

• Rinse for 1 minute.

Treatment of tress with shampoo.

• Homogenize the formulation via an overhead stirrer (20 min, 300 rpm).

• Pretreat the tress.

• Weight out 0.8 grams of shampoo (0.2 g of shampoo per one gram of hair tress).

• Massage for 45 seconds.

• Rinse for 30 seconds. Water volume rate 60-70 ml/second.

• Re-apply shampoo once.

(3) Combing test.

• Dip in the water.

• Comb, speed of combing 300 mm/min.

• With two fingers, remove the excess water.

• Comb, speed of combing 300 mm/min.

• Perform combing test.

• Repeat the step 15 times.

2.7. Procedure for dry combing and data interpretation.

In order to evaluate the conditioning performance of the studied actives the following procedure was used:

1. The hair tresses were washed with solution of SLES (concentration 14 %; pH = 6).

2. The tresses were dried in climatic room at controlled conditions: relative humidity = 57 %; Temperature = 20 °C.

3. The tresses were subjected to a coming test (speed of combing 300 mm/min) via a comb with narrow teeth (11 teeth per centimeter). At least 10 passes were applied. The average initial total work for combing is calculated (JEBEFORE).

4. The tress was than treated with shampoo formulation, as described in the previous section. 5. The tress again dried at the same conditions (relative humidity = 57 %; Temperature = 20 °C).

6. The tresses were subjected to a coming test (speed of combing 300 mm/min) via a comb with narrow teeth (11 teeth per centimeter). At least 10 passes were applied. The average total work for combing is calculated (JTAFTER).

7. The dimensionless work reduction is calculated, JTDL, via equation (1).

8. The water content of the tress is measured via the procedure described in the next section.

2.8. Measurement of the water content in hair tresses.

Information on the water content of the hair tresses is of essential importance for the interpretation of the experimental results. That is why it is measured via the following procedure.

(1) 2 g grams of hair fibers was taken from the bottom part of the tress.

(2) The hair fibers were put in a thermo gravimetric balance (producer: Mettler Toledo; model: HX204). This equipment allows real-time measurement of the mass of a sample during heating.

(3) The sample was heated at 105°C for a period of time, which is automatically determined by the equipment. The heating is stopped when there is no measurable change in the humidity.

(4) From the information of the initial and final mass of the tresses, the initial water content of the tress is calculated.

2.9. Measurement of the contact angle on hair fiber.

In the following the principle of the measurement of contact angle on hair fiber is described. The measurement protocol is described in detail in Appendix A. The contact angle on treated hair fibers was measured via tensiometer Kruss K14. The tresses used in this case are home bleached. As shown in ref. 6 the home bleached tresses allow for better reproducibility and therefore clearer evaluation of the experimental trends. The fiber is cut 5 cm from the root. The radius of the fiber is measured via a micrometer. The fiber is dipped in water container with the cuticles directed toward the end of the tip of the fiber placed in the container.

The instrument measures the downward force, F, exerted on the fiber via a sensitive force sensor, and calculates the contact angle from the following expression:

F = Z ycos(0A) (2) Here F is the force exerted by the capillary force on the fiber; L is the perimeter of the wetted hair fiber, calculated form the radius R of the hair fiber; 0A is advancing contact angle. This measurement is performed for 10 hair fibers. The outliers of the measurement are removed via the following procedure in Microsoft Excel:

1. The values of the first, QI and third, Q3 quartiles of the data are calculated.

2. After that the interquartile value is calculated IQV = Q3-Q1.

3. The lower and upper acceptable values are calculated via the following formulas:

LAV = Q1-1.5*IQV

UAV = Q1+1.5*IQV

If a specific value of the contact angle is outside the range LAV-UAV, it is discarded.

Quartile is a type of quantile which divides the number of data points into four parts, or quarters, of more-or-less equal size. The data must be ordered from smallest to largest to compute quartiles; as such, quartiles are a form of order statistic. The three main quartiles are as follows: The first quartile (QI) is defined as the middle number between the smallest number (minimum) and the value that falls between the 25th and 75th percentiles of the sample (which cuts off the first quarter of all the samples). It is also known as the lower quartile, as 25% of the data is below this point. The second quartile (Q2) is the median of a data set; thus 50% of the data lies below this point. The third quartile (Q3) is the middle value between the value that cuts off the last quarter of samples and the highest value (maximum) of the data set. It is known as the upper quartile, as 75% of the data lies below this point.

2.10. Measurement of the deposition of actives on hair fibers.

The fraction of the deposited actives (oil or DV920) on the tresses was measured. The actives were extracted from the treated tresses via organic solvent. After that the obtained solution was analyzed via liquid chromatography (triglyceride) or gas chromatography (DV920). The concentration of the respective active in the solution was calculated with the help of a calibration curve for the respective active, build prior to the experiment. This information was then used to calculate the mass fraction of the active deposited on the tress; more precisely the fraction of total active, present in the formulation, which remained on the tress. The procedure is described in detail in Appendix B. 2.11. Sensorial panels in hairdresser’s saloon (shampoo formulations).

The sensorial tests of the shampoo formulations were performed via the following procedure.

(1) The hair of the model is washed for 1 min.

(2) The shampoo is applied on the hair for 1.5 minutes. The system of interest is applied to the left, while the benchmark is applied to the right, 6 grams of product each. In some cases, more shampoo was applied (10 g), this is done for longer and/or thicker hairs. During this process the properties of foam are assessed in terms of:

• Flash foam (ease of foam generation).

• Foam amount.

• Feeling of the foam.

• Appearance (brightness) of the foam.

• Appearance of the bubbles (size, size distribution).

(3) The shampoo is rinsed off from the hair in the following sequence: (1) 30 seconds, right side; (2) 30 seconds, left side; (3) 45 seconds, right side; (4) 45 seconds, left side. During this step, the sensorial perception of the hair is evaluated with respect to the following parameters:

• Ease of rinsing.

• Sensorial perception of the hair.

(4) The hair is combed and the time for combing of each side is measured.

(5) The sensorial properties of the hair in wet state are evaluated, namely:

• Ease of detangling.

• Softness (roots and lengths).

• Softness (tips).

• Cleanliness.

• Lightness.

(6) The hair is dried, and the time for drying is measured.

(7) The sensorial properties of the hair in dry state is evaluated, namely:

• Speed of drying.

• Manageability.

• Cleanliness.

• Shine.

• Softness (roots and lengths).

• Softness (tips). • Homogeneity of treatment.

• Anti-electrostatic.

• Hair vitality.

• Untied effect.

• Lightness.

In the end of the panel the hairdresser makes a preference regarding the product with better performance, and explains the rationale of her/his choice. In these tests models with Caucasian hair with damaged hair level 3-5 were employed.

Appendix A

Protocol for the measurement of the contact angle of hair fibers

Hair treatment

Materials:

- Tresses

- Pre-treatment solution 14% pH: 6

- Gloves

- Syringe 2 ml

- Comb

- Stopwatch

- Thermometer

- Metronome

- Test tube 21

Pre-treatment:

- Leave the wicks to soak for 15 minutes in the water.

- Check the flow rate (1100ml +/- 40ml for 10s), the water temperature (36.5°C +/- 1°C) and the water hardness if not done (set point: Ix/week).

- Remove the wick from the soaking tank and hang it on the rack. Wring out the wick roughly.

- Use the syringe to withdraw 2ml of washing solution for one wick. Apply the solution to the entire length of the wick.

- Massage for 1 minute (30s per side) at a metronome pace (108 bips/min).

- Rinse for 1 minute under water (30s per side) with fingertips, following the metronome rhythm (58 bips/min).

- Comb through until you get an easy comb through (wide gap). Repeat all these steps a second time.

Treatment of the tresses:

- Draw up 0.8 ml of shampoo with the syringe. Apply the solution to the entire length of the strand.

- Massage for 45 seconds at a metronome pace (108bips/min).

- Rinse for 30 seconds under water (15s per side) with fingertips, respecting the metronome rhythm (58bips/min).

- Wring out the strand in 1 pass

- Comb through until the comb passes easily (wide gap).

Repeat all these steps a second time.

Contact angle measurement

Materials:

- Scissors

- Pliers

- Aluminum foil

- Crystallizer (25ml)

- Micrometer

To measure the contact angle of the hair fibres it is important to always measure the surface tension of the water in which the fibres will be soaked. This step is very important in order to verify that the water is completely free of impurities which could distort the results.

- Measurement of the surface tension of (distilled) water

Clean the crystallizer with DECON90 and rinse with tap water and distilled water. Do not put your fingers inside the crystallizer when rinsing. Allow to dry on a clean surface.

- Fill the crystallizer with distilled water.

- Place the crystallizer on the balance platform.

- Then hang the rod on the scale.

- Close the scale doors and turn on the scale.

- To measure the surface tension of the water you will then need the platinum blade and a small hook

- Heat the platinum blade twice with the Bunsen burner. - Hang the hook, then the turntable blade on the hook and raise the platform using the knob on the right of the scale until the water level is flush with the blade without touching it.

Surface and Interfacial Tension was measured using the KRUSS Laboratory Desktop 3.2 application.

- Measure as many times as necessary to obtain a tension of 72.5 mN/m. If the tension is too low, either the crystallizer is not clean or the water temperature is above 20°C.

Hair selection

- Select a fiber and place it on paper: root to top of the stem

- Using a ruler, cut about 5 cm from the root and 5 cm from the tip

- Measure the diameter of the fiber: using the pliers, grab the fiber and position it in the micrometer.

- Place the fibre on the small sticky tip and cut so that 3/4 mm of hair remains above the tip

- Check that the fibre is positioned straight.

Measurement of the hair contact angle

Place the small tip where the hair is attached on the rod and place the rod on the scale

- Raise the platform until the water level is flush with the hair

- Make sure that the hair is straight, if not, straighten it without damaging it with the small pliers.

Appendix B

Protocol of the measurement with LC/MS, GC

SAMPLE PREPARATION :

- Weigh a known quantity of hair (typically few hundreds mg) in a flask,

- Add approx, few ml of extraction solvent (mixture cH2ci2-MeOH) and Vortex.

- Remove the liquid part and perform a second extraction then vortex.

- Join the liquid fractions and evaporate to dryness.

- Perform L/L washing by adding H2O and CH2C12

- Remove the aqueous phase,

- Evaporate the organic phase again to dryness,

- Add BuOH in order to solubilize the analyte - Filter the solution obtained then analyzed by HPLC/MS or GC/MS according to the analyte.

The analytical methods are described below:

HPLC/MS method GC/MS Method

The disclosed subject matter has been described with reference to specific details of particular embodiments thereof. It is not intended that such details be regarded as limitations upon the scope of the disclosed subject matter except insofar as and to the extent that they are included in the accompanying claims.

Therefore, the exemplary embodiments described herein are well adapted to attain the ends and advantages mentioned as well as those that are inherent therein. The particular embodiments disclosed above are illustrative only, as the exemplary embodiments described herein may be modified and practiced in different but equivalent manners apparent to those skilled in the art having the benefit of the teachings herein. Furthermore, no limitations are intended to the details of construction or design herein shown, other than as described in the claims below. It is therefore evident that the particular illustrative embodiments disclosed above may be altered, combined, or modified and all such variations are considered within the scope and spirit of the exemplary embodiments described herein. The exemplary embodiments described herein illustratively disclosed herein suitably may be practiced in the absence of any element that is not specifically disclosed herein and/or any optional element disclosed herein. While compositions and methods are described in terms of "comprising," "containing," or "including" various components or steps, the compositions and methods can also "consist essentially of or "consist of the various components, substances and steps. As used herein the term "consisting essentially of shall be construed to mean including the listed components, substances or steps and such additional components, substances or steps which do not materially affect the basic and novel properties of the composition or method. In some embodiments, a composition in accordance with embodiments of the present disclosure that "consists essentially of the recited components or substances does not include any additional components or substances that alter the basic and novel properties of the composition. If there is any conflict in the usages of a word or term in this specification and one or more patent or other documents that may be incorporated herein by reference, the definitions that are consistent with this specification should be adopted.

Claims

1. A cosmetic composition comprising a mixture of (A) one or more vegetable oils and (B) one or more co-active substances (B), wherein the co-active substance(s) (B) are chemically modified oils, selected from the group consisting of (i) oil oligomers derived from triglycerides or liquid esters, (ii) oil-based estolides derived from triglycerides or liquid esters, and (iii) linear or branched hydrocarbons.

2. The composition according to claim 1 wherein the one or more vegetable oils (A) are selected from the group consisting of Coriander seed oil, Groundnut oil, Rice bran wax, Evening primrose oil, Apricot kernel oil, Grapeseed oil, Rice bran oil, Linseed oil, Mongongo oil, Hibiscus oil, Babassu seed oil, Hazelnut oil, Wheatgerm oil, Baobab oil, Rose flower oil, Corngerm oil, Walnut seed oil, Canola (Rapeseed) oil, Brazil nut oil, Baobab seed oil, Moringa Oleifera Seed oil, Camelina sativa seed oil, Babassu nut oil, Camellia oil, Macadamia Integrifolia S. oil, Crambe oil, Manila oil, Sesame seed oil, Macadamia Ternifolia S. oil, Soybean oil, Avocado oil, Jojoba seed oil, Safflower oil, Shea butter, Argan oil, Guar oil, Coconut oil, Mango oil, Pracaxi oil, Pumpkin Seed oil, Grape Seed oil, Pequi oil, Passion Fruit oil, Amaranthus oil, Kokum oil, Cassia oil, and Sunflower oil.

3. The composition according to claim 1 or 2, wherein the vegetable oil(s) (A) is one or more selected from the group, consisting of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Argan oil, and Coconut oil.

4. The composition according to any one of claims 1 to 3, wherein the vegetable oil (A) comprises one or more of monoglycerides, diglycerides, triglycerides, mixtures of mono- di- and triglycerides, and liquid esters, and/or wherein the co-active substance (B) is one or more, selected from the group, consisting of dicarboxylic acid and epoxidized triglycerides polyester, dicarboxylic acid and epoxidized vegetable oil polyester, hydrogenated castor oil (and) hydrogenated castor oil/dicarboxylic acid copolymer (and) Cs-Ci4 carboxylic acid.

5. The composition according to any one of claims 1 to 4, wherein the co-active substance (B) is selected from the group, consisting of

- Sebacic acid and epoxidized triglycerides polyester

- Sebacic acid and epoxidized Jojoba oil polyester

- Hydrogenated Castor oil (and) Hydrogenated Castor oil/Adipic Acid Copolymer (and) Caprylic/Capric Triglyceride.

6. The composition according to any one of claims 1 to 5, wherein the oil-based estolides (ii) are derived from vegetable oil triglycerides or liquid esters, optionally grafted with fatty acids with a length of 6 or 12 carbon atoms, and/or wherein the oil based estolides (ii) are derived from

- Lauric acid and epoxidized triglycerides polyester

- Lauric acid and epoxidized jojoba oil polyester

- Hexanoic acid and epoxidized triglycerides polyester

- Hexanoic acid and epoxidized jojoba oil polyester

- Hexanoic acid and epoxidized jojoba oil polyester.

7. The composition according to any one of claims 1 to 6, wherein the vegetable oil is one or more, selected from the group, consisting of Avocado oil, Baobab oil, Guar oil, Amaranthus oil, Argan oil and Coconut oil.

8. The composition according to any one of claims 1 to 7, wherein the weight ratio of the vegetable oil (A) to the co-active substance (B) is 40:60 to 70:30, preferably 50:50.

9. The composition according to any one of claims 1 to 8, wherein the composition comprises one or more hydrocarbons, preferably said hydrocarbons being liquid or solid hydrocarbons, oils or waxes, are selected from one or more C6-C90 straight or branched hydrocarbons, more preferably selected from straight or branched Ce-Ceo hydrocarbons.

10. A skincare or haircare composition, comprising the cosmetic composition according to any one of claims 1 to 9.

11. The composition according to claim 10 , said composition further comprising one or more ingredients, selected from the group, consisting of a pH regulating system, emollient(s), excipient(s), a surfactant system, guar, rheology modifier(s), antioxidant(s), conditioning polymer(s) and solubilization agent(s), said composition preferably comprising citric acid in a pH regulating system, said composition more preferably comprising cationic/non cationic surfactant(s) in an amount from 10% to 25% by weight, based on 100% total weight of the composition.

12. The composition according to claim 10 or 11, further comprising a sulfated or non-sulfated chassis.

13. The composition according to any one of claims 10 to 12, which has a silicone oil content of 0,001 % or less based on the total weight of the composition.

14. The composition according to any one of claims 10 to 13, wherein the content of the vegetable oil (A) and the co-active substance (B) is 0,1-20% preferably 0,25-5%, more preferably 0,5-2%, based on the total weight of the composition.

15. Use of a composition of the preceding claims in hair care compositions, preferably in hair conditioning compositions, preferably wherein said use is for increasing hair hydrophobicity.

16. Use of a composition of the preceding claims in skincare compositions.

17. A method for preparing a chemically modified vegetable oil, said method comprising:

(i) a glycerolysis step comprising reacting a vegetable oil with glycerin using a lipase as catalyst, and

(ii) an esterification step comprising esterification of the product of step (i) with a dicarboxylic acid.

18. The method according to claim 17, wherein the vegetable oil is selected from the group, consisting of Coconut oil, Babassu oil, Crambe oil, Pequi oil, Mango oil, Grape oil, Maracuja oil, Pumpkin Seed oil and Pracaxi oil, and/or wherein the dicarboxylic acid is selected from the group, consisting of adipic acid and sebacic acid.

19. A chemically modified vegetable oil obtained by the process of any one of claims 17 or 18.