Quaternary ammonium salt for use as a cationic surfactant

Abstract

The object of the invention concerns a quaternary ammonium salt of formula (I) wherein the substituents R.sub.5, R.sub.6 are independently chosen between hydrogen H and a radical R.sub.0, wherein the radical R.sub.0 consists of the structure of formula (II) wherein the substituent R.sub.1 is chosen from the group consisting of: hydrogen, methyl, isopropyl, sec-butyl, isobutyl, ethylenemethylthio, benzyl, para-hydroxybenzyl and 3-methylene-1H-indole, wherein the substituents R.sub.2, R.sub.3, R.sub.4 are independently chosen from the group consisting of: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, wherein m is an integer number comprised between 1 and 22, wherein the counteranion X.sup.− is chosen from the group of carboxylic acids consisting of: formic acid, acetic acid, unsaturated monocarboxylic acids, tartaric acid, adipic acid, aldaric acid, oxalic acid, phthalic acid, azelaic acid, sebacic acid, malonic acid, succinic acid, glutaric acid, pimelic acid, maleic acid, malic acid, fumaric acid, suberic acid, citric acid, isocitric acid, fatty acids, acid amino acids, keto acids and aromatic carboxylic acids, and wherein n is comprised between 2 and 20.

Claims

1. Quaternary ammonium salt of formula (I) ##STR00019## wherein the substituents R.sub.5, R.sub.6 are independently chosen between hydrogen and a radical R.sub.0 wherein the radical R.sub.0 consists of the following structure of formula (II) ##STR00020## wherein the substituent R.sub.1 is chosen from the group consisting of: hydrogen, methyl, isopropyl, sec-butyl, isobutyl, ethylenemethylthio, benzyl, para-hydroxybenzyl and 3-methylene-1H-indole, wherein the substituents R.sub.2, R.sub.3, R.sub.4 are independently chosen from the group consisting of: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, wherein the counteranion mX.sup.− is chosen from the group of carboxylic acids consisting of: formic acid, acetic acid, unsaturated monocarboxylic acids, tartaric acid, adipic acid, aldaric acid, oxalic acid, phthalic acid, azelaic acid, sebacic acid, malonic acid, succinic acid, glutaric acid, pimelic acid, maleic acid, malic acid, fumaric acid, suberic acid, citric acid, isocitric acid, fatty acids, amino acids, keto acids and aromatic carboxylic acids, wherein m is an integer number comprised between 1 and 22, wherein n is comprised between 2 and 20.

2. Salt of formula (I) according to claim 1, wherein n is comprised between 2 and 10.

3. Salt of formula (I) according to claim 1, wherein m is an integer number comprised between 1 and 12.

4. Salt of formula (I) according to claim 1, wherein, R.sub.5 is hydrogen, R.sub.6 is hydrogen, m is equal to 1, and the counteranion X.sup.− is the acetate ion or the malate ion or the citrate ion or the tartrate ion.

5. Salt of formula (I) according to claim 1, wherein R.sub.5 is equal to R.sub.0, R.sub.6 is hydrogen, m is equal to 1 or 2, and the counteranion X.sup.− is the acetate ion or the malate ion or the citrate ion or the tartrate ion or mixtures of the foregoing.

6. Salt of formula (I) according to claim 1, wherein R.sub.5 is equal to R.sub.0, R.sub.6 is equal to R.sub.0, m is equal to 1 or 2 or 3, n is equal to 3, and the counteranion X.sup.− is the acetate ion or the malate ion or the citrate ion or the tartrate ion or mixtures of the foregoing.

7. Salt of formula (I) according to claim 1, wherein R.sub.1 is hydrogen.

8. Composition comprising at least one salt of formula (I) according to claim 1, as a cationic surfactant.

9. Composition according to claim 8, wherein the salt of formula (I) is in a concentration comprised between about 0.25% and 7.00% (w/w) by weight on the total weight of the composition.

10. Composition according to claim 8, comprising the salt of formula (I) as the sole cationic surfactant or in combination with other cationic surfactants.

11. Composition according to claim 8, having a pH higher than 3.5 and less than 6.

12. Composition according to claim 8, the composition being a cosmetic composition.

13. Composition according to claim 12, in the form of a skin and hair cleansing product, a hair conditioning product, a skin moisturising product.

14. Composition according to claim 13, wherein the hair conditioning product comprises fatty alcohols with a number of carbon atoms comprised between 14 and 22.

15. Composition according to claim 8, the composition being a cleaning or conditioning/softening composition for surface treatment.

16. Composition according to claim 15, wherein the surface treatment is a treatment chosen from the group consisting of: cleaning treatments of inert surfaces, leather or textiles, anti-static treatments of inert surfaces or textiles, softening treatments of textiles or leather, treatments for the care or maintenance of inert surfaces, leather or textiles and combinations of the foregoing.

17. Composition according to claim 15, comprising, in addition to the salt of formula (I), suitable excipients and/or diluents.

Description

DESCRIPTION OF THE DRAWINGS

[0036] FIG. 1—Synthesis scheme of the salt of formula (I)

[0037] FIG. 2—Tensiometer instrument (INSTRON Mod. 5543)

[0038] FIG. 3—Comparison between strand of hair treated according to example 2.1. Left-hand strand: the hair is smoother and more moisturised to the touch; healthier to the eye. A reduction in the frizz and fly-away effect is also visible; right-hand strand: the hair is more frizzy and the onset of the fly-away effect is visible.

[0039] FIG. 4—Measurement of dry detangling of hair.

[0040] FIG. 5—Measurement of the detangling capacity on damaged Caucasian and Chinese hair, treated with a 5% aqueous solution of salt of formula (I.sub.A1) and an equal amount of a 5% aqueous solution of a 50:50 combination of CTAC/BTAC.

[0041] FIG. 6—Measurement of the thickness assessed on five hair strands after 20 brush strokes.

[0042] FIG. 7—Measurement of the hair breakage after 10 brush strokes.

[0043] FIG. 8—Method for measuring the electrostatic charge.

DETAILED DESCRIPTION OF THE INVENTION

[0044] Salt of Formula (I)

[0045] With reference to formula (I), the invention will be described hereinbelow in more detail, referring where necessary to the preferred embodiment of the invention.

[0046] The substituent R.sub.1 of the salt of formula (I) is selected from the group consisting of: hydrogen, methyl, isopropyl, sec-butyl, isobutyl, ethylenemethylthio, benzyl, para-hydroxybenzyl and 3-methylene-1H-indole.

[0047] It should be noted that, depending on whether the substituents R.sub.5 and R.sub.6 are equal to hydrogen (—H) or to the radical R.sub.0 (formula II), the value of m may change accordingly.

[0048] In general, m with reference to the counteranion X.sup.− represents the number of molecules of the counteranion contained in the salt of formula (I). Preferably, m is a number such that it guarantees the neutrality of the molecule of the salt of formula (I). In particular, m is an integer number comprised between 1 and 22, preferably comprised between 1 and 12, preferably comprised between 1 and 8, preferably equal to 1 or 2 or 3 or 4 or 5 or 6 or 7.

[0049] According to a particularly preferred embodiment, the salt of formula (I), comprises, at most, a number of quaternary ammonium groups equal to 3, irrespective of the value of n. In other words, the quaternary ammonium molecule and its counteranion X.sup.− are preferably between them in a stoichiometric ratio equal to 1:1 or alternatively equal to 1:2 or alternatively equal to 1:3, regardless of the value of n.

[0050] The following Table 1 shows the structural formulas of the different preferred embodiments of the salt of formula (I) for each substituent R.sub.1.

TABLE-US-00001 TABLE 1 For- mula R.sub.1 (name) Structure hydro- gen (I.sub.A) [00003] methyl (I.sub.B) [00004] Iso- propyl (I.sub.C) [00005] Iso- butyl (I.sub.D) [00006] Sec- butyl (I.sub.E) [00007] ethyl- ene- methyl- thio (I.sub.F) [00008] Benzyl (I.sub.G) [00009] Para- hy- droxy- benzyl (I.sub.H) [00010] 3- methyl- ene- 1H- indole (I.sub.I) [00011]

[0051] Preferably, R.sub.1 is hydrogen; in other words, the preferred embodiment of the salt of formula (I) is (I.sub.A).

[0052] For each of the embodiments indicated in Table 1 (I.sub.A-I.sub.I), the substituents R.sub.2, R.sub.3, R.sub.4 are independently chosen from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

[0053] According to a preferred embodiment of the salts of formula (I.sub.A-I.sub.I), at least two of the substituents chosen between R.sub.2, R.sub.3, R.sub.4 are equal to each other and preferably chosen from the group consisting of methyl, ethyl, n-propyl, n-butyl (e.g., R.sub.2, R.sub.4) and the remaining substituent is preferably chosen from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

[0054] According to a preferred embodiment of the salts of formula (I.sub.A-I.sub.I), at least two of the substituents chosen between R.sub.2, R.sub.3, R.sub.4 are equal to each other and preferably methyl (e.g., R.sub.2, R.sub.4) and the remaining substituent is preferably chosen from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

[0055] The substituents R.sub.2, R.sub.3 and R.sub.4 of the salt of formula (I) are preferably equal to each other and are chosen among the linear substituents: methyl, ethyl, n-propyl, n-butyl.

[0056] The substituents R.sub.2, R.sub.3 and R.sub.4 of the salt of formula (I) are preferably equal to each other and consist of the linear methyl substituent.

[0057] According to a preferred embodiment, the substituents R.sub.2, R.sub.3 and R.sub.4 of the salt of formula (I.sub.A) are equal to each other and consist of the linear methyl substituent.

[0058] It should be noted that the considerations made above with reference to the substituents R.sub.2, R.sub.3, R.sub.4 apply to both the quaternary ammonium group of the salt of formula (I) and to the radical R.sub.0.

[0059] For each of the embodiments indicated in Table 1 (I.sub.A-I.sub.I), the counteranion mX.sup.− is chosen from the group of carboxylic acids (in the form of carboxylate ions) consisting of: [0060] monocarboxylic acids, preferably chosen between acetic acid and formic acid; [0061] unsaturated monocarboxylic acids, among which the acrylic acid is preferred one; [0062] bicarboxylic (or dicarboxylic) acids, preferably chosen from the group consisting of: adipic acid, aldaric acid, oxalic acid, phthalic acid, azelaic acid, sebacic acid, malonic acid, succinic acid, tartaric acid, glutaric acid, pimelic acid, maleic acid, malic acid, fumaric acid, suberic acid; [0063] tricarboxylic acids, preferably chosen between citric acid and isocitric acid; [0064] fatty acids, preferably chosen from the group consisting of butyric acid, oleic acid, palmitic acid, stearic acid; [0065] acid amino acids, preferably chosen from the group consisting of glutamic acid and aspartic acid; [0066] keto acids, preferably chosen between: acetoacetic acid, pyruvic acid and levulinic acid; and [0067] aromatic carboxylic acids, preferably chosen from the group consisting of benzoic acid, salicylic acid, cinnamic acid, caffeic acid.

[0068] It should be noted that fatty acids are defined as saturated or unsaturated aliphatic monocarboxylic acids with a number of carbon atoms ≥4 and ≤20, preferably ≥4 and ≤18.

[0069] For the purposes of the present invention, the keto acids are carboxylic acids which contain a ketone residue and which are involved in various biological processes, such as, for example, the process of forming ketone bodies or of glycolysis.

[0070] For the embodiment (I.sub.A) of the quaternary ammonium salt of the invention, the counteranion X.sup.− is preferably chosen from the group of carboxylic acids (in the form of carboxylate ions) consisting of: formic acid, acetic acid, acrylic acid, adipic acid, aldaric acid, oxalic acid, phthalic acid, azelaic acid, sebacic acid, malonic acid, succinic acid, tartaric acid, glutaric acid, pimelic acid, maleic acid, malic acid, fumaric acid, suberic acid, citric acid, isocitric acid, butyric acid, oleic acid, palmitic acid, stearic acid, glutamic acid, aspartic acid, acetoacetic acid, pyruvic acid, levulinic acid, benzoic acid, salicylic acid, cinnamic acid, caffeic acid.

[0071] A polyglycerol-n is defined as a polymer consisting of an n number of structural-base units of glycerol; it should be noted that the commonly commercially available polyglycerols-n are mixtures of polyglycerols, comprising 60% or more of the polyglycerol-n of interest in which about 20% of the mixture consists of one or more of its different homologues, i.e., polyglycerols-n with a lower or higher n number of repeating units than the one considered.

[0072] In particular, a polyglycerol-n in which n≤10 can be synthesised using green experimental methods starting from natural plant glycerine, following the Cosmos and NaTrue standards.

[0073] In contrast, a polyglycerol-n in which n>10 is normally obtained by experimental methods known to the person skilled in the art which include the use of synthetic (non-vegetable) glycerin.

[0074] According to a preferred embodiment of the quaternary ammonium salt of formula (I), n is comprised between 2 and 10, preferably comprised between 2 and 6, preferably equal to 2, 3, 4 or 5.

[0075] In solution (or mixture), the quaternary ammonium salt of formula (I) is preferably electrically neutral. For the purposes of the present invention, electrically neutral means a molecular structure that contains an equal number of positive charges and of negative charges.

[0076] Embodiments in which the substituent R.sub.5 is hydrogen and the substituent R.sub.6 is hydrogen According to a preferred embodiment of the salt of formula (I), preferably of the salt of formula (I.sub.A), the substituent R.sub.5 is equal to hydrogen H and the substituent R.sub.6 is hydrogen.

[0077] In this preferred embodiment, the salt of formula (I), preferably the salt of formula (I.sub.A), is characterised by a single positive charge on the quaternary nitrogen N.

[0078] According to this preferred embodiment, the value of m is preferably equal to 1. Still preferably, in this first preferred embodiment, the positive charge of the quaternary nitrogen is neutralised by the counteranion mX.sup.−, which satisfies the following conditions [0079] m is equal to 1 and X.sup.− is a monoprotic carboxylic acid (or monocarboxylic acid), preferably it is the acetic acid; [0080] or alternatively [0081] m is equal to 1 and X.sup.− is a pluriprotic carboxylic acid but with only one ionisable/ionised carboxylic group, preferably it is the malic acid or the citric acid or the tartaric acid.

[0082] It should be noted that, preferably, the degree of ionisation of the pluriprotic carboxylic acid is influenced by the pH conditions of the chemical environment in which the salt of formula (I) is placed, preferably the salt of formula (I.sub.A), or to those of the process at which the quaternisation thereof takes place. In fact, although the quaternisation reaction carried out under acid catalysis is advantageous because it uses the carboxylic acid destined to neutralise the quaternary N, the same reaction can also be carried out under alkaline catalysis.

[0083] Embodiments in which the Substituent R.sub.5 is Equal to the Radical R.sub.0 and the Substituent R.sub.6 is Hydrogen

[0084] According to a preferred embodiment of the salt of formula (I), preferably of the salt of formula (I.sub.A), the substituent R.sub.6 is hydrogen, the substituent R.sub.5 is equal to the radical R.sub.0, characterised by the following structure of formula (II):

##STR00012##

[0085] According to this embodiment, the substituent R.sub.1 of R.sub.0 is selected from the group consisting of: hydrogen, methyl, isopropyl, sec-butyl, isobutyl, ethylenemethylthio, benzyl, para-hydroxybenzyl and 3-methylene-1H-indole.

[0086] Preferably, R.sub.1 of R.sub.0 is hydrogen; for the substituents R.sub.2, R.sub.3, R.sub.4, the above considerations apply.

[0087] According to a particularly preferred embodiment mode of the present embodiment, the substituents R.sub.2, R.sub.3 and R.sub.4 of R.sub.0 are equal to each other and consist of the linear methyl substituent.

[0088] According to this preferred embodiment, the salt of formula (I), preferably of formula (I.sub.A), is characterised by a double positive charge on the corresponding quaternary nitrogen atoms N.

[0089] According to this preferred embodiment, the value of m may preferably be equal to 1 or 2. Still preferably, the positive charges of the quaternary nitrogen atoms are neutralised under the following conditions: [0090] m is equal to 1 and X.sup.− is a totally ionised diprotic carboxylic acid (or dicarboxylic acid), preferably it is the malic acid or the tartaric acid; [0091] m is equal to 1 and X.sup.− is a triprotic carboxylic acid (or tricarboxylic acid) with only two ionisable/ionised carboxylic groups, preferably it is the citric acid; [0092] m is equal to 2 and X.sup.− is a monoprotic carboxylic acid, preferably it is the acetic acid; or [0093] m is equal to 2 and X.sup.− is a pluriprotic carboxylic acid with only one ionisable/ionised carboxylic group, preferably it is the malic acid, the tartaric acid or the citric acid or combinations of the foregoing.

[0094] Still preferably, when the substituent R.sub.5 is equal to R.sub.0 and m is equal to 2, the two counteranions X.sup.− neutralising the two positive charges of the nitrogen atoms of the salt of formula (I), preferably of formula (I.sub.A), may consist of the same carboxylic acid (same entity) or of two carboxylic acids of different nature (different entity).

[0095] The Applicant hereinafter describes particularly preferred embodiments of the salt of formula (I.sub.A).

[0096] Embodiments in which the Substituent R.sub.5 and the Substituent R.sub.6 are Equal to the Radical R.sub.0

[0097] According to a preferred embodiment of the salt of formula (I), preferably of the salt of formula (I.sub.A), the substituents R.sub.6 and R.sub.5 are equal to the radical R.sub.0 (formula II) and equal to each other.

##STR00013##

[0098] According to this embodiment, the substituent R.sub.1 of R.sub.0 is selected from the group consisting of: hydrogen, methyl, isopropyl, sec-butyl, isobutyl, ethylenemethylthio, benzyl, para-hydroxybenzyl and 3-methylene-1H-indole.

[0099] Preferably, R.sub.1 of R.sub.0 is hydrogen; for the substituents R.sub.2, R.sub.3, R.sub.4, the above considerations apply.

[0100] According to a particularly preferred embodiment mode of the present embodiment, the substituents R.sub.2, R.sub.3 and R.sub.4 of R.sub.0 are equal to each other and consist of the linear methyl substituent.

[0101] According to this preferred embodiment, the salt of formula (I), preferably of formula (I.sub.A), is characterised by a plurality of positive charges on the corresponding quaternary nitrogen atoms N.

[0102] Still preferably, the salt of formula (I), preferably of formula (I.sub.A), is characterised by a maximum of 3 quaternary ammonium groups and thus by three positive charges on the corresponding quaternary nitrogen atoms N, irrespective of the value of n.

[0103] According to this preferred embodiment, the value of m may preferably be equal to 1 or 2 or 3. Still preferably, the positive charges of the quaternary nitrogen atoms are neutralised under the following conditions: [0104] m is equal to 1 and X.sup.− is a totally ionised triprotic carboxylic acid (or tricarboxylic acid), preferably it is the citric acid; [0105] m is equal to 2 and X.sup.− is a mixture of a monoprotic carboxylic acid (or monocarboxylic acid) and a totally ionised diprotic carboxylic acid (or dicarboxylic acid), preferably chosen between acetic acid, malic acid, citric acid, tartaric acid and combinations of the foregoing; [0106] m is equal to 2 and X.sup.− is a partially ionised pluriprotic carboxylic acid, preferably chosen from acetic acid, malic acid, citric acid, tartaric acid and combinations of the foregoing; [0107] m is equal to 3 and X.sup.− is a monoprotic carboxylic acid, preferably it is the acetic acid; or [0108] m is equal to 3 and X.sup.− is a pluriprotic carboxylic acid with only one ionisable/ionised carboxylic group, preferably it is the malic acid, the tartaric acid or the citric acid or combinations of the foregoing.

[0109] Still preferably, when the substituent R.sub.5 is equal to R.sub.0 and m is equal to 2, the two counteranions X.sup.− neutralising the two positive charges of the nitrogen atoms of the salt of formula (I), preferably of formula (I.sub.A), may consist of the same carboxylic acid (same entity) or of two carboxylic acids of different nature (different entity).

[0110] The Applicant hereinafter describes particularly preferred embodiments of the salt of formula (I.sub.A).

First Preferred Embodiment of the Salt of Formula (I.SUB.A.)

[0111] According to a first preferred embodiment of the salt of formula (I.sub.A), the substituents R.sub.5 and R.sub.6 are both hydrogen, m is equal to 1, the substituent R.sub.1 is hydrogen, the substituents R.sub.2, R.sub.3 and R.sub.4 are methyl, as well as in the following formula:

##STR00014##

[0112] Preferably n is equal to 2, 3, 4 or 5.

[0113] According to this first preferred embodiment, the counteranion X.sup.− is acetate. The acetate counteranion is particularly advantageous for the purposes of the invention because it gives the quaternary ammonium salt of formula (I) a pleasant fruity smell.

Second Preferred Embodiment of the Salt of Formula (I.SUB.A.)

[0114] According to a further preferred embodiment of the salt of formula (I.sub.A), the substituents R.sub.5 and R.sub.6 are both hydrogen, m is equal to 1, the substituent R.sub.1 is hydrogen, the substituents R.sub.2, R.sub.3 and R.sub.4 are methyl and the counteranion X.sup.− is malate, as well as in the following formula (I.sub.A2):

##STR00015##

[0115] Preferably n is equal to 2, 3, 4 or 5.

[0116] The Applicant points out that the malate ion as depicted in formula (I.sub.A2) is for illustrative purposes only and not limiting the purposes of the invention.

[0117] For the purposes of the present invention, the malate is preferably the dicarboxylate ion of the natural enantiomer of the malic acid, namely the L-form (or 2S-hydroxy-1,4-butanedioic acid), which is the one biologically active.

Third Preferred Embodiment of the Salt of Formula (I.SUB.A.)

[0118] A third embodiment is the quaternary ammonium salt characterised by the following structure formula (I.sub.A3), wherein the substituent R.sub.5 is equal to the radical R.sub.0, R.sub.6 is hydrogen, R.sub.1 is hydrogen, the substituents R.sub.2, R.sub.3 and R.sub.4 are methyl groups, wherein m is equal to 2 and the counteranion X.sup.− is acetate:

##STR00016##

[0119] Preferably n is equal to 2, 3, 4 or 5.

[0120] According to an alternative embodiment of the salt of Formula I.sub.A3 X.sup.− is the monoionised malate ion or the monoionised tartrate ion and m is equal to 2.

Fourth Preferred Embodiment of the Salt of Formula (I.SUB.A.)

[0121] A fourth embodiment of the invention is the quaternary ammonium salt characterised by the following structure formula (I.sub.A4), wherein the substituent R.sub.5 is equal to the radical R.sub.0, R.sub.6 is hydrogen, R.sub.1 is hydrogen, the substituents R.sub.2, R.sub.3 and R.sub.4 are methyl groups, wherein m is equal to 1 and the counteranion X.sup.− is the malate ion or the tartrate ion:

##STR00017##

[0122] According to this fourth embodiment of structure formula (I.sub.A4), n is equal to 2, 3, 4, or 5.

Fifth Preferred Embodiment of the Salt of Formula (I.SUB.A.)

[0123] A fifth embodiment of the invention is the quaternary ammonium salt characterised by the following structure formula (I.sub.A5), wherein the substituents R.sub.5 and R.sub.6 are equal to the radical R.sub.0, R.sub.1 is hydrogen, the substituents R.sub.2, R.sub.3 and R.sub.4 are methyl groups, wherein m is equal to 1 or 3 and the counteranion X.sup.− is the citrate ion or the acetate ion:

##STR00018##

[0124] According to this fourth embodiment of structure formula (I.sub.A4), n is equal to 2, 3, 4, or 5. Still preferably, the number of quaternary ammonium groups is equal to 3, regardless of the n value.

[0125] The quaternary ammonium salt of formula (I) can be advantageously obtained using the reactions known in the state of the art: by way of example, FIG. 1 shows the synthesis scheme of the quaternary ammonium salt of formula (I.sub.A) starting from the trimethylglycine acidification reaction (reaction I, FIG. 1), and subsequent organic acid catalysed esterification reaction with the polyglycerol-n reagent (reaction II, FIG. 1). In this way, the desired quaternary ammonium salt product of formula (I.sub.A) and water are obtained.

[0126] It should be noted that, advantageously, water is the only by-product of the synthesis reaction of the quaternary ammonium salt of formula (I); thus, there is no formation and/or potential release of other compounds or chemical derivatives into the environment.

[0127] As with the quaternary ammonium salt of formula (I.sub.A), the synthesis reaction of the quaternary ammonium salt of formula (I) can be carried out starting from amino acid derivatives characterised by a quaternary amine group at carbon α (N—R.sub.2, R.sub.3, R.sub.4).

[0128] Advantageously, the starting amino acid derivative (N—R.sub.2, R.sub.3, R.sub.4), the polyglycerol-n and the organic acid used in these chemical reactions are in turn obtained, as far as possible, by green synthesis methods according to the Cosmos and NaTrue standards and the Regulation (EC) No. 1223/2009, thus contributing to the sustainability of the final product.

[0129] Composition Comprising at Least One Salt of Formula (I) as a Cationic Surfactant

[0130] The salt of formula (I), preferably of formula (I.sub.A), is preferably used as a cationic surfactant.

[0131] Preferably, the salt of formula (I) is used as a wetting agent, conditioning/softening, emulsifying, cleaning, antistatic agent.

[0132] As already anticipated, further object of the present invention is a composition comprising at least one quaternary ammonium salt formula (I) as a cationic surfactant, in combination with possible excipients and/or diluents.

[0133] In the composition claimed preferably the salt of formula (I) is in a concentration comprised between about 0.25% and 7% (w/w), preferably between about 0.25% and 5%, preferably between about 0.5% and 5% (w/w), preferably between about 1% and 5% (w/w), preferably equal to about 0.25%, 0.5%, 1%, 2%, 3%, 4%, 5% (w/w) by weight on the total weight of the composition.

[0134] In the composition comprising the salt of formula (I), the latter may be the sole cationic surfactant or may be in combination with other cationic surfactants.

[0135] When used in combination with other cationic surfactants (e.g. polymeric cationic surfactants), at the dosages indicated above, the salt of formula (I) enables the use of silicone derivatives to be avoided or the use of other polymeric cations to be reduced.

[0136] Cationic surfactants that can be used in combination with the salt of formula (I) are, for example, chosen from the group consisting of: cetrimonium chloride (or CTAC), behentrimonium chloride (or BTAC), stearamidopropyl dimethylamine (or SAPDMA) and guar hydroxypropylthrimethylammonium chloride (or GHPTAC), Dioleylethyl Hydroxyethylmonium Methosulfate (Tetranil CO-40) and Behenoyl PG-Trimonium Chloride (Quartamina BTC-131).

[0137] The composition preferably has a pH higher than 3.5 and less than 6.0; preferably the cosmetic composition has a pH comprised between 3.5 and 5, preferably comprised between 4 and 4.5.

[0138] The pH of the composition can be regulated by including one or more buffering agents in the composition; an average person skilled in the art, on the basis of his basic knowledge, would be able to select without any difficulty one or more suitable buffering agents for the purpose, choosing among those known to be state of the art.

[0139] Cosmetic Composition Comprising the Salt of Formula (I)

[0140] According to an embodiment of the invention, the composition comprising the salt of formula (I), preferably of formula (I.sub.A), is of the cosmetic type.

[0141] The cosmetic composition comprising the salt of formula (I) may further comprise suitable excipients and/or diluents known to the person skilled in the art. By way of example, suitable excipients and/or diluents are selected among: water; cationic surfactants; anionic surfactants; amphoteric surfactants; conditioning agents; active ingredients, e.g. proteins, amino acids, osmoprotectants, vitamins; anti-dandruff agents; thickening agents; viscosity agents; filming agents, emulsifiers; antioxidants; chelators; pigments for hair colouring; buffering agents for pH regulation; natural extracts; fragrances; essential oils; humectants.

[0142] The cosmetic composition preferably has a pH higher than 3.5 and less than 6.0; preferably a pH comprised between 3.5 and 5, preferably comprised between 4 and 4.5.

[0143] Without wishing to be bound by any theory, the Applicant believes that the pH influences the conditioning capacities of a cationic system; in this sense, at the above-mentioned pH values, the cosmetic composition has shown better conditioning capacities: the hair could be more easily combed than at other pH values of the composition.

[0144] The pH of the cosmetic composition can be regulated by including one or more buffering agents in the composition; an average person skilled in the art, on the basis of his basic knowledge, would be able to select without any difficulty one or more suitable buffering agents for the purpose, choosing among those known to be state of the art.

[0145] The cosmetic (or cosmetic type) composition is preferably in the form of a cleansing product for the skin and hair, a conditioning product for the hair or a moisturising product for the skin.

[0146] When in the form of a cleansing product for the skin and hair, the cosmetic composition is preferably in the form of shampoo, conditioning shampoo (2-in-1), bath foam.

[0147] According to a preferred embodiment, the cosmetic composition in the form of a skin and hair cleanser comprises the salt of formula (I) in a concentration comprised between about 1 and 3%.

[0148] When in the form of a hair conditioning product, the cosmetic composition is in the form of an oil non oil conditioner or hair conditioner.

[0149] According to a preferred embodiment, the cosmetic composition in the form of a hair conditioning product comprises the salt of formula (I) in a concentration comprised between about 1 and 7%.

[0150] When in the form of a skin moisturising product, the cosmetic composition is preferably in the form of a moisturising cream.

[0151] According to a preferred embodiment, the cosmetic composition in the form of a skin moisturising cream comprises the salt of formula (I) in a concentration comprised between 1 and 3%.

[0152] When used as the sole cationic surfactant in hair cosmetic compositions, the quaternary ammonium salt of formula (I) shows comparable or more advantageous effects than common surfactants (see section Example 2).

[0153] According to a preferred embodiment, the cosmetic composition is in the form of a hair conditioning product and preferably comprises a fatty alcohol with a number of carbon atoms comprised between 14 and 22, preferably comprised between 16 and 18.

[0154] Preferably, the fatty alcohol contained in the composition is chosen from the group consisting of cetyl alcohol, stearyl alcohol or a combination of the foregoing (cetylstearyl alcohol). According to a preferred embodiment, the amount of alcohol is comprised between 1.10% and 2.20% by weight with respect to the amount of salt of formula (I).

[0155] The association with fatty alcohols advantageously promotes the combability, reducing the force needed for the operation of combing the hair with a smoother comb passage.

[0156] Composition Comprising the Salt of Formula (I) for Surface Treatment

[0157] The salt of formula (I), preferably of formula (I.sub.A), is preferably used as a cationic surfactant.

[0158] Preferably, the salt of formula (I) is used as a wetting agent, conditioning/softening, emulsifying, cleaning, antistatic agent.

[0159] A further object of the present invention is a cleaning, softening/conditioning composition for surface treatment.

[0160] It should be noted that by surfaces it is intended both the household and non-household surfaces (objects, worktops, floors); leather surfaces; textile or fabric surfaces.

[0161] Preferably, the compositions for surface treatment that can be formulated with the quaternary ammonium salt of formula (I) are liquid compositions.

[0162] Preferably, the surface treatment comprises cleaning treatments of inert surfaces, leather or textiles, anti-static treatments of inert surfaces or textiles, softening treatments of textiles or leather, treatments for the care or maintenance of inert surfaces, leather or textiles and combinations of the foregoing.

[0163] In particular, the composition for surface treatment preferably comprises the salt of formula (I) in combination with any excipients and/or diluents.

[0164] It should be noted that diluents suitable for preparing compositions for surface treatment in accordance with the invention include: [0165] water: the compositions for surface treatment according to the present invention preferably contain water as the sole or main vehicle. [0166] solvents: they are used as washing additives or diluents in order to modulate the viscosity of the final product. Suitable solvents for the purposes of the invention are for example ethanol, glycerol, cetyl alcohol, fatty acids, monoglycerides, diglycerides and triglycerides.

[0167] It should be noted that organic solvents are generally used in the preparation of compositions for surface treatment when also synthetic surfactants are introduced in addition to the salt of formula (I). In order to make a composition for surface treatment green (hence that does not contain synthetic surfactants), the cetyl alcohol can be used as a solvent.

[0168] Composition for surface treatment comprising the salt of formula (I) according to the invention which preferably contains solvents in an amount comprised between 0 and 6% by weight on the total weight of the composition.

[0169] Composition for surface treatment comprising the salt of formula (I) according to the invention preferably containing water in an amount comprised between 0 and 95%, preferably between 0 and 90% by weight on the total weight of the composition.

[0170] Suitable excipients for the composition for surface treatment in accordance with the invention include, for example: chelators; amphoteric surfactants; cationic surfactants; pH control buffering systems; metal ion control agents; dyes; pigments; smell control agents (such as for example cyclodextrins); perfumes; essential oils; preservatives; anti-microbial agents; anti-mould agents; anti-oxidants; anti-corrosion agents; enzymes; water softening agents, bentonite, zeolite and combinations of the foregoing.

[0171] In the composition for surface treatment according to the invention preferably the salt of formula (I) is in a concentration comprised between about 0.25% and 7% (w/w), preferably between about 0.25% and 5%, preferably between about 0.5% and 5% (w/w), preferably between about 1% and 5% (w/w), preferably equal to about 0.25%, 0.5%, 1%, 2%, 3%, 4%, 5% (w/w) by weight on the total weight of the composition.

[0172] In the composition for surface treatment, the salt of formula (I) may be the only cationic surfactant or may be in combination with other cationic surfactants.

[0173] When used in combination with other cationic surfactants (e.g. polymeric cationic surfactants) or cationic/non-ionic surfactants or non-ionic surfactants, at the dosages indicated above, the salt of formula (I) allows the reduction of other polymeric cations.

[0174] Cationic surfactants that can be used in combination with the salt of formula (I) are, for example, chosen from the group consisting of: cetrimonium chloride (or CTAC), behentrimonium chloride (or BTAC), stearamidopropyl dimethylamine (or SAPDMA) and guar hydroxypropylthrimethylammonium chloride (or GHPTAC), Dioleylethyl Hydroxyethylmonium Methosulfate (Tetranil CO-40) and Behenoyl PG-Trimonium Chloride (Quartamina BTC-131).

[0175] In the composition for surface treatment, the salt of formula (I) can be used in combination with non-ionic surfactants. Non-ionic surfactants that can be used are preferably chosen among: polyoxyethylene derivatives of fatty acids and alkyl-poly-glucosides or APGs, preferably they are APGs. Preferably, if the composition for surface treatment contains APGs, these may be generically chosen among ethanolamides, ethoxylated amides, ethoxylated amines, ethoxylated acids, cetomacrogol and mixtures thereof, preferably the non-ionic surfactant is chosen among Lauryl Polyglucoside, Cocamido propylamine oxide and mixtures of the foregoing.

[0176] The composition for surface treatment has preferably a pH higher than 3.5 and less than 6.0; preferably, the cosmetic composition has a pH comprised between 3.5 and 5, preferably comprised between 4 and 4.5.

[0177] Without wishing to be bound by any theory, the Applicant believes that the pH influences the conditioning/softening and anti-static capacities of a cationic system; in this sense, at the above pH values, the composition for surface treatment has shown improved conditioning/softening or anti-static capacities.

[0178] The pH of the composition for surface treatment can be regulated by including one or more buffering agents in the composition; an average person skilled in the art, on the basis of his basic knowledge, would be able to select without any difficulty one or more suitable buffering agents for the purpose, choosing among those known to be state of the art.

[0179] According to a preferred embodiment, the composition for surface treatment in the form of a detergent comprises the salt of formula (I) in a concentration comprised between 0.25% and 5%, preferably comprised between 0.25% and 2.5%, preferably comprised between 0.5% and 2%, preferably equal to 0.5%, 1%, 1.5% and 2% by weight, on the total weight of the composition (w/w).

[0180] When in the form of a conditioning/softening product, the composition comprises the salt of formula (I) in a concentration comprised between 0.5% and 7%, preferably comprised between 0.5% and 6%, preferably comprised between 1.5% and 5.5%, preferably equal to 2%, 2.5% 3%, 3.5%, 4%, 4.% 5% by weight, on the total weight of the composition (w/w).

EXAMPLES

[0181] The Applicant provides hereinbelow examples for illustrative and non-limiting purposes of cosmetic use of the salt of formula (I).

Example 1—Examples of Compositions Comprising the Salt of Formula (I) for Cosmetic Use

[0182] 1.1—Conditioning Shampoo

TABLE-US-00002 Ingredients (INCI) Basic shampoo A Basic shampoo B Sodium Laureth Sulfate 8.5 10.0  Cocamidopropyl Betaine — 3.0 Lauryl Hydroxysultanine 3.0 — PEG-4 Rapeseedamide — 2.0 Glicereth-2 Cocoate 2.0 — Salt of formula (I.sub.A1) 3.0 3.0 Citric acid at pH 5 qs qs Water at 100 at 100 Preservative q s q s Perfume q s q s

[0183] 1.2—Conditioning Shampoo (2-in-1)

TABLE-US-00003 Category Ingredient (INCI) % w/w Primary surfactant Sodium Coceth-2 Sulphate 12 Auxiliary surfactants Sodium Cocoamphoacetate 5 Cocamidopropylamine Oxide 3 Cocamidopropyl Betaine 4 Conditioners Salt of formula (I) 3 Guar Hydroxypropyltrimonium 1 Chloride Hydroxypropyltrimonium 1 Chloride Solvent Aqua (water) at 100 Active ingredients Hydrolized Keratin 1 Panthenol 0.5 Thickener PEG-120 Methyl Glucose 1 Trioleate, Propylen Glycol Sequestrant Tetrasodium EDTA 0.1 Perfume and q.s. preservatives

[0184] 1.3—Green Conditioning Shampoo (2-in-1)

TABLE-US-00004 Category Ingredient (INCI) % w/w Primary surfactant Sodium Lauroyl Glutamate 12 Auxiliary surfactants Sodium Cocoamphoacetate 5 Cocamidopropyl Hydroxysultanine 3 Cocamidopropyl Betaine 4 Conditioners Salt of formula (I.sub.A1) 3 Distearoylethyl Hydroxyethylmonium 1 Methosulfate Solvent Aqua (water) at 100 Active ingredients Arctium Lappa Root Extract 1 Spirulina Maxima Powder 0.5 Thickener Xanthan Gum 1 Sequestrant Tetrasodium Glutamate Diacetate 0.1 Perfume and q.s. preservatives

[0185] 1.4—Hair Conditioner

TABLE-US-00005 Category Ingredient (INCI) % w/w Emulsifier Polyglyceryl-3 Cetyl Ether, 4 Sesame Oil, Malic Acid Surfactant Cocamidopropyl Betaine 3 Thickeners/ Cetearyl Alcohol 1.5 stabilisers Myristyl Alcohol 1 Functional Argan Oil 1 substances Cetyl Dimethicone 0.5 Conditioners Salt of formula (I) 5 Behenamidopropyl Dimethylamine 2 Solvent Aqua (water) at 100 Active ingredients Phytantriol 1 Sericin 0.5 Urtica Dioica Leaf Extract 1 Sequestrant Tetrasodium EDTA 0.1 Perfume and q.s. preservatives

[0186] 1.5—‘Oil not Oil’ Hair Conditioner

TABLE-US-00006 Category Ingredient (INCI) % w/w Solubiliser Polyglyceryl-6 Caprylate, Proline, 3 Aqua Fixative VP/Dimethylaminoethylmethacrylate 2 Copolymer Solvent Aqua (water) at 100 Caprylyl Glycol 3 Ethanol 10 Conditioner Salt of formula (I) 3 Polyquaternium-10 1 Thickener Methyl Gluceth-20 2 Active ingredient Panthenol 1 Sequestrant Tetrasodium EDTA 0.1 Perfume and q.s preservatives

[0187] 1.6—After-Bath Body Cream

TABLE-US-00007 Category Ingredient (INCI) % w/w Emulsifier Polyglyceryl-6 Oleate, 5 Potassium Olivate Emollients Persea Gratissima Oil 3 Prunus Amygdalus Dulcis Oil 3 Butyrospermum Parkii 2 Caprylic/Capric Triglyceride 5 Thickeners/ Glyceryl Stearate 2 Stabilisers Cetyl Palmitate 1 Cetearyl Alcohol 1 Functional Sodium PCA 1 substances Glycerin 3 Urea 0.5 Conditioners Salt of formula (I) 5 Solvent Aqua (water) at 100 Active ingredients Sodium Hyaluronate 1 Bisabolol 0.5 Hydrolyzed Mallow Leaf Extract 1 Sequestrant Tetrasodium EDTA 0.1 Perfume and q.s preservatives

Example 2—Experimental Evidence Relative to the Cosmetic Use

[0188] 2.1—Visual Assessment

[0189] In the picture in FIG. 3 it is possible to visually compare how a strand of hair treated with the cosmetic product comprising the salt of formula (I.sub.A1) (on the left) looks like after drying and a strand of hair treated with a product comprising common quaternary cationic surfactants (quat) after drying (on the right).

[0190] 2.2—Method for Measuring the Combability

[0191] Caucasian hair strands of the same origin were washed for 1 minute with a shampoo and then treated for 1 minute with a hair conditioning product formulated with the quaternary ammonium salt of the invention and with conditioning products formulated with different cationic ingredients (control).

[0192] The combability measurements were then carried out with a tensiometer (INSTRON Mod. 5543, speed 500 mm/min) on both wet and dry hair (FIG. 2).

[0193] In order to facilitate the interpretation of the results obtained by the Applicant, it should be noted that combability means the force that the hair opposes to the sliding of the comb, i.e. the measurement of the resistance that the hair exerts on the passage of the comb.

[0194] 2.3—Measurement of Dry Detangling of Hair

[0195] The graph in FIG. 4 shows the dry detangling values of damaged Caucasian hair, obtained by performing the method according to Example 2.2.

[0196] In particular, the hair was combed following the treatment with a conditioning shampoo and the conditioning shampoo of Example 1.1.

[0197] 2.4—Measurement of the Detangling Capacity on Damaged Caucasian and Chinese Hair

[0198] The graph in FIG. 5 shows the dry detangling (combability) values of damaged Caucasian hair, obtained by performing the method according to Example 2.2.

[0199] In particular, the hair was combed following the treatment with a 5% aqueous solution of salt of formula (I.sub.A1) and an equal amount of a 5% aqueous solution of a 50:50 combination of CTAC/BTAC.

[0200] The result of the treatment comprising the salt of formula (I.sub.A1) shows better and significant benefits in the operation of dry hair combing (method in Example 2.2), if compared to the result obtained with the common quats, such as CTAC or BTAC.

[0201] In addition, the action of the salt of formula (I.sub.A1) ensures a noticeable moisturising sensation on damaged hair.

[0202] 2.5—Hair Thickness Measurement Assessed on Five Strands of Hair after 20 Brush Strokes

[0203] The assessment was carried out on strands washed with the Green shampoo of example 1.3, compared with two traditional, market-leading products. The results are shown in the graph in FIG. 6, expressed as a percentage increase in hair volume (before and after treatment).

[0204] Although the composition with the salt of formula (I.sub.A1) is merely for illustrative purposes, the results are fully comparable with the complex and sophisticated compositions of products from major multinational companies containing synthetic ingredients.

[0205] 2.6—Hair Breakage Measurement after 10 Brush Strokes

[0206] The assessment was carried out on strands washed with the Green shampoo of example 1.3, compared with two traditional, market-leading used previously products (Control 1 and Control 2).

[0207] The results of this comparison can be seen in the graph in FIG. 7.

[0208] 2.7—Method for Measuring the Electrostatic Charge (Static Charge Build-Up—Lunn & Evans Method).

[0209] The same strands of hair used for the combability tests were dried and combed 10 times under standard environmental conditions (20° C., relative humidity RH=30%) and then the static charge (V) was measured with an appropriate sensor (3M Electical Specialties Division, Model 709).

[0210] The detection was carried out 10 times and the average of the values obtained was calculated.

[0211] From the results shown in the graph in FIG. 8, it was found that a cosmetic product comprising the salt of formula (I.sub.A1) acts as an effective static charge reducer.

[0212] The electrostatic charge abatement effect is higher when compared to that achieved with market-leading products comprising quaternary monoalkyl linear chains of CTAC and BTAC.

Example 3—Examples of Compositions Comprising the Salt of Formula (I) for Surface Treatment

[0213] 3.1—Composition in the Treatment of Leather, Textile Surfaces or Fabrics

TABLE-US-00008 Salt of formula (I) 5-7% Non-ionic surfactants (e.g. APG)  <5% Acidifier (e.g. citric acid) q.s. Sequestrant q.s. Perfume and preservatives q.s. Water at 100

[0214] 3.2—Composition in the Treatment of Leather, Textile Surfaces or Fabrics

TABLE-US-00009 Salt of formula (I)   5% Acidifier (e.g. citric acid) pH 4 q.s. PERFUME  0.5% DYE q.s. PRESERVATIVE (MIT/BIT 5%) 0.25% Water at 100

[0215] 3.3—Composition in the Treatment of Surfaces (Objects, Worktops, Floors)

TABLE-US-00010 APG (e.g. Lauryl Polyglucoside) 4-5% Cocamido propylamine oxide 3-5% Salt of formula (I) 2-4% Sequestrant (e.g. Tetrasodium Glutamate Diacetate) q.s. Perfume, preservatives and dyes q.s. Water at 100