Cosmetic salt

Abstract

Disclosed herein are salts of formula I, where q is + or -; p is 2+, +, -, or 2-; g is 1 or 2; G is R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - , R 5 -C≡C-SO2 - , R 5 -C≡CS(=O)S - , R 5 -C≡C-SO3 - , R 5 -C≡CS(=O)2S - and a diallylammonium group, where R 5 are independently H, straight or branched chain C 1-6 alkyl; L is selected from linear C 1-15 alkyl, where one or more CH groups are independently -(CH-O-CH)-, -(CH-CH-O)-, -(O-CH-CH)-, C=O, -O-, -S-, -NH-, or -NR 1 -, where R 1 is linear or branched C 1-6 alkyl; A is NR 2 3 + , CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , and S(=O)2S - where R 2 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; E is selected from NR 3 2. NR 3 3 + , CO2H, C(=O)SH, CS2H, SO2H, S(=O)SH, SO3H, S(=O)2SH, CO2 - , C(=O)S - , CS2 - , SO2- , S(=O)S - , SO3 - , S(=O)2S - where R 3 is independently in each occurrence H, straight or branched chain C 1-6 provided that the overall charge of A and E is not zero, and the salt of formula I has an overall neutral charge. Further disclosed are cosmetic formulations comprising the salt of formula I, as well as the use of such salts or formulations as hair care products. TIFF2025511296000030.tif1656

Description

[Technical field]

[0001] The present disclosure relates to salts and cosmetic formulations thereof, and their use as hair care products. Additionally, methods of treating keratinous materials, such as hair, are disclosed. [Background technology]

[0002] Human hair has a highly organized but complex structure. It consists of a hair follicle embedded in the skin and a hair shaft extending from the skin. Hair is usually composed of two or three layers. The outermost layer is the cuticle, the middle layer is the cortex, and in some cases there is a central medulla region made of densely packed cells and / or cavities. Most of the mass of human hair is made up of fibrous structures called macrofibrils, each of which is made up of microfibrils held together by matrix proteins. Human hair is composed of 65-95% protein by weight, most of which is keratin, a fibrous, helical protein that is particularly rich in the amino acid cysteine, whose thiol groups can form disulfide bridges, providing rigidity and resistance to the entire hair structure.

[0003] During various hair treatments, such as bleaching, dyeing, straightening, and permanent waving, hair can be over-processed and damaged by the chemicals required to bring about the desired changes. For example, some known hair straightening processes consist of treatment with alkaline straighteners. The high pH (9.0-14.0) causes the hair to swell, and the alkaline agents penetrate the hair fiber and react with the keratin, causing the breaking and rearrangement of disulfide bridges present in the keratin, resulting in the hair being stretched. In addition to the chemically induced damage, physical treatments such as frequent and / or high heat or environmental exposure can cause changes in the hair's texture, often leading to permanent damage. Summary of the Invention

[0004] It is highly desirable to avoid, minimize, reduce or repair any such damage that occurs during these hair treatment processes, and to be able to specifically repair disulfide cross-links to restore and improve hair quality, strength and texture.

[0005] The object of the present disclosure is to advance the state of the art of hair repair.A further object of the present disclosure is to provide salts and formulations for use as hair care products, preferably capable of cross-linking thiol moieties.The cross-linked thiol moieties can be formed, for example, by the cleavage of disulfide bridges as a result of physical or chemical hair treatment.A further object of the present disclosure is to enhance the repair of disulfide bridges in hair using the linker of the present invention.

[0006] The applicant has developed a thiol-reactive crosslinker that can crosslink thiol moieties, thus mimicking disulfide bridges. The thiol moieties to be crosslinked may result from prior cleavage of disulfide bridges, for example, as a result of physical or chemical hair treatment. By crosslinking thiol moieties, the thiol-reactive crosslinker disclosed herein effectively enables the restoration of disulfide bridges.

[0007] The present disclosure relates in a first aspect to a salt of formula I: [ka] During the ceremony, q is + or -; p is 2+, +, -, or 2-; g is 1 or 2; G is R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - , R 5 -C≡C-SO2 - , R 5 -C≡CS(=O)S- , R 5 -C≡C-SO3 - , R 5 -C≡CS(=O)2S - and a diallylammonium group, where R 5 are independently H, straight or branched chain C 1-6 alkyl; L is linear C 1-15 alkyl, where one or more CH groups are independently -(CH-O-CH)-, -(CH-CH-O)-, -(O-CH-CH)-, C=O, -O-, -S-, -NH-, or -NR 1 -, where R 1 is linear or branched C 1-6 is alkyl; A is NR 2 3 + , CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , and S(=O)2S - where R 2 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; E is NR 3 2. NR 3 3 + , CO2H, C(=O)SH, CS2H, SO2H, S(=O)SH, SO3H, S(=O)2SH, CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , S(=O)2S - where R 3 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; However, the overall charge of A and E is not zero, and the salt of formula I has an overall neutral charge.

[0008] In some embodiments, the disclosure relates to a salt of formula II: [ka] During the ceremony, q is + or -; p is 2+, +, -, or 2-; g is 1 or 2; G is R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - , R 5 -C≡C-SO2 - , R 5 -C≡CS(=O)S - , R 5 -C≡C-SO3 - , R 5 -C≡CS(=O)2S - , and (CH2=CH-CH2) i NR 4 (4-i) + where i is independently selected from 2 and 3, and where R 4 are independently H, straight or branched chain C 1-6 alkyl, where R 5 are independently H, straight or branched chain C 1-6 alkyl; A is NR 2 3 + , CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , S(=O)2S - where R 2 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; E is NR 3 2. NR3 3 + , CO2H, C(=O)SH, CS2H, SO2H, S(=O)SH, SO3H, S(=O)2SH, CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , S(=O)2S - where R 3 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; M is O, S, NH, and NR 1 where R 1 is a linear or branched chain C 1-6 is alkyl; m and n are independently selected from 1, 2, and 3; x and y are independently selected from 0, 1, and 2; However, the overall charge of A and E is not zero, and the salt of formula I has an overall neutral charge.

[0009] In some embodiments of the salt of formula I or II, the diallylammonium group is a moiety of formula d1 or d2: [ka] wherein R4 in each occurrence is independently H, straight or branched chain C 1-6 is selected from alkyl.

[0010] In some embodiments of the salt of formula I or II, G is R 5 C≡C-CO2 - , R 5 C≡CC(=O)S - , R 5 C≡C-CS2 - , R 5 C≡C-SO2 - , R 5 C≡CS(=O)S - , R 5 C≡C-SO3- , R 5 C≡CS(=O)2S - , and (CH2=CH2CH2) i NR 4 r + where i is selected from 2 and 3, r is selected such that the sum of i and r is 4, and R 5 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; R 4 is independently in each occurrence H, straight or branched chain C 1-6 In some embodiments of the salt of formula I or II, G is selected from R 5 C≡C-CO2 - and (CH2=CH2CH2) i NH (4-i) + where i is selected from 2 and 3; R 5 is H, straight or branched chain C 1-6 In some embodiments of the salt of formula I or II, G is selected from HC≡C-CO2. - and (CH2=CH2CH2)2NH2 + is selected from.

[0011] In some embodiments, the disclosure relates to a salt of formula III: [ka] During the ceremony, M is O, S and NR 6 where R 6 is H, straight or branched chain C 1-6 alkyl; R 5 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; m and n are independently selected from 1, 2, and 3; x and y are independently selected from 0, 1, and 2.

[0012] In some embodiments of the salt of formula III, R 5 is H and M is O.

[0013] In some embodiments of the salt of Formula III, m and n are independently selected from 2 or 3. In preferred embodiments of the salt of Formula III, m and n are both selected from 2 or 3.

[0014] In some embodiments, the disclosure relates to a salt of formula IV: [ka] During the ceremony, M is O, S, and NR 6 where R 6 is H, straight or branched chain C 1-6 alkyl; R 4 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; m and n are independently selected from 1, 2, and 3; x and y are independently selected from 0, 1, and 2.

[0015] In some embodiments of the salt of formula IV, R 4 is H and M is O.

[0016] In some embodiments of the salt of Formula IV, m and n are independently selected from 1 and 2.

[0017] In some embodiments of the salt of formula II, III, or IV, m is equal to n. In some embodiments of the salt of formula II, III, or IV, m is equal to n and x is equal to y. In some embodiments of the salt of formula II, III, or IV, m is equal to n and x is different from y.

[0018] In a second aspect, the present disclosure relates to a cosmetic formulation comprising at least one salt according to any of the embodiments described herein.

[0019] In some embodiments of the cosmetic formulation, the cosmetic formulation further comprises at least one cosmetic additive selected from the group consisting of surfactants, oil components, emulsifiers, pearlescent waxes, consistency improvers, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithin, phospholipids, sun protection agents, moisturizers, biogenic agents, antioxidants, deodorants, antiperspirants, antidandruff agents, film formers, bulking agents, insect repellents, self-tanning agents, tyrosine inhibitors (bleaching agents), hydrotropes, solubilizers, preservatives, fragrance oils and dyes, and mixtures thereof.

[0020] In some embodiments of the cosmetic formulation, the cosmetic formulation further comprises a carrier, preferably selected from water, a C(2-6)-alcohol, a C(1-10) polyol, and an oil component.

[0021] In a third aspect, the present disclosure relates to a salt, a composition, or a cosmetic formulation according to any of the embodiments described herein for use as a hair care product.

[0022] In a fourth aspect, the present disclosure relates to the use of a salt according to any of the embodiments described herein for the manufacture of a cosmetic formulation, preferably for the manufacture of a hair care product.

[0023] In a fifth aspect, the present disclosure relates to a method for the treatment of keratinous material, such as hair, comprising the step of applying a salt or cosmetic formulation according to any of the embodiments described herein to the keratinous material.

[0024] The salts and cosmetic formulations disclosed herein are suitable for cosmetic applications, particularly for protecting healthy hair or improving damaged hair. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0025] In the context of the present disclosure, repair of disulfide bridges refers to the process of linking two thiol moieties (it is understood that the term "disulfide bridge" refers to the linking of two thiol moieties using the salt of the present invention, and does not refer to a directly linked -SS- bond). The thiol moiety may be, for example, part of a keratin protein. The process of linking thiol moieties may involve the reaction of each thiol with an electrophilic moiety in the crosslinker. The thiol-reactive crosslinkers disclosed herein generally react with two thiol moieties to form a crosslinking unit linking the two thiol moieties.

[0026] Unless otherwise specified, the following general definitions apply to all salts of the present disclosure as described.

[0027] As used herein, the term "salt of the present disclosure" refers to any of the salts represented by Formulas I-IV and the specific examples disclosed herein.

[0028] "Independently of each other" is understood to mean that when a radical occurs more than once in any salt, its definition on each occurrence is independent of any other occurrence.

[0029] -C 1-4 It is further understood that an unattached dashed or solid line, such as an alkyl, represents a point of attachment of a residue (ie, a partial formula).

[0030] It is further understood that the abbreviations "C" and "N" represent all possible degrees of saturation that do not normally result in a radical, nitrene or carbene, i.e., N includes -NH-, -N=, and TIFF2025511296000007.tif1415 is included, where C is -CH2-, =CH-, and In addition, the substituent R x"C" as an atom in an aromatic or heteroaromatic ring includes =CH- as well as =CR x In addition, the substituent R x "C" as an atom in an aromatic or heteroaromatic ring not containing the radicals =CH- and TIFF2025511296000009.tif1513 is included. It is understood and known to those skilled in the art that the general rules of valency must be followed.

[0031] In any formula, a linear or branched alkyl chain, such as a linear or branched C 1-15 It is understood that whenever multiple CH2 groups of alkyl are replaced by heteroatoms or heteroatom-containing groups, the two or more CH2 groups are replaced in such a way that directly adjacent multiple heteroatoms, such as -OO- or -NH-NH-, are avoided.In particular, two or more CH2 groups should be replaced so that the alkyl chain does not contain peroxide groups.The same applies to the selection of general groups defined herein, such as L, and are selected in such a way that directly adjacent multiple heteroatoms, such as -OO- or -NH-NH-, are avoided.

[0032] The term "diallyl ammonium group" refers to a positively charged nitrogen atom covalently bonded to four substituents, where at least two of the four substituents are allyl substituents. An example of a "diallyl ammonium group" is (CH2=CHCH2)2NR2 + , (CH2=CHCH2)3NR + , (CH2=CHCH2)4N + , (CH2=C(CH3)CH2)2NR2 + , (CH2=C(CH3)CH2)3NR + , (CH2=C(CH3)CH2)4N + , ((CH3)HC=CCH2)2NR2 + , ((CH3)HC=CCH2)3NR + , ((CH3)HC=CCH2)4N + , ((CH3)2C=CCH2)2NR2+ , ((CH3)2C=CCH2)3NR + , ((CH3)2C=CCH2)4N + where R is independently selected from H and straight or branched chain C 1-6 In some embodiments, a "diallyl ammonium group" refers to a positively charged nitrogen atom covalently bonded to four substituents, where two of the four substituents are aryl substituents and the other two substituents are not aryl substituents. In some embodiments, a "diallyl ammonium group" refers to a (CH2=CHCH2)2NR2 + where R is independently H and straight or branched chain C 1-6 In some embodiments, the "diallyl ammonium group" can be selected from the group consisting of (CH2=CHCH2)2NH2 + It is.

[0033] When E and Z isomers exist, such as in the crotyl fragment ((CH3)HC=CCH2-), the E isomer, Z isomer, and mixtures thereof are included.

[0034] An "aryl substituent" or "aryl" is one or more C 1-6 It refers to a -CH2CH=CH2 unit which may be optionally substituted with an alkyl group. Examples of "aryl" include -CH2CH=CH2, -CH(CH3)CH=CH2, -C(CH3)2CH=CH2 units -CH2C(Me)=CH2, -CH2CH=CH(CH3)(E and Z), -CH2CH=C(CH3)2. In some embodiments, "aryl" is -CH2CH=CH2.

[0035] "C 1-14 Alkyl, C 1-12 Alkyl, C 1-11 Alkyl, and C 1-6 The term "alkyl" refers to a fully saturated branched or unbranched hydrocarbon moiety having the indicated number of carbon atoms. 1-14Representative examples of alkyl include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, neohexyl, heptyl, octyl, nonyl, decyl, dodecyl, and the like. 1-6 Representative examples of alkyl include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, or neohexyl. 1-14 Alkyl, C 1-12 Alkyl, C 1-11 Alkyl and C 1-6 One or more adjacent or non-adjacent CH groups of the alkyl are independently replaced with one or more groups selected from -(CH-O-CH)-, -(CH-CH-O)-, and -(O-CH-CH)-, C=O, -O-, -S-, -NH-, -NR-, where R is a straight or branched C 1-6 It is an alkyl.

[0036] Certain parameters such as p and q used herein refer to charge. Charge can be, for example, 2+, +, -, or 2-. 2+ refers to two positive charges, i.e., each ion is twice as positively charged. Conversely, 2- refers to two negative charges, i.e., each ion is twice as negatively charged. Charge usually refers to an ion, but an ion can be an entire chemical moiety, fragment, or entity. The charge of an ion refers to the total charge of that ion and can be calculated by adding up all the positive and negative charges contained in the ion. As an example, an ion containing an ammonium group and two carboxylate groups will have a total charge of -. The charge of an ion may be delocalized across multiple atoms. The charge may also be localized to a small number of atoms, such as one atom.

[0037] Based on the definitions given throughout the application, one of skill in the art will be familiar with which combinations are synthetically feasible and practical; for example, combinations of groups resulting in several heteroatoms directly bonded to each other, e.g. -OO-, are generally not considered, but synthetically feasible combinations such as -SN= in isothiazoles are considered.

[0038] In a first aspect, the present disclosure relates to a salt of formula I: [ka] During the ceremony, q is + or -; p is 2+, +, -, or 2-; g is 1 or 2; G is R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - , R 5 -C≡C-SO2 - , R 5 -C≡CS(=O)S - , R 5 -C≡C-SO3 - , R 5 -C≡CS(=O)2S - and a diallylammonium group, where R 5 are independently H, straight or branched chain C 1-6 alkyl; L is linear C 1-15 alkyl, where one or more CH groups are independently -(CH-O-CH)-, -(CH-CH-O)-, -(O-CH-CH)-, C=O, -O-, -S-, -NH-, or -NR 1 -, where R 1 is linear or branched C 1-6 is alkyl; A is NR 2 3 + , CO2 -, C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , and S(=O)2S - where R 2 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; E is NR 3 2. NR 3 3 + , CO2H, C(=O)SH, CS2H, SO2H, S(=O)SH, SO3H, S(=O)2SH, CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , S(=O)2S - where R 3 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; However, the overall charge of A and E is not zero, and the salt of formula I has an overall neutral charge.

[0039] In some embodiments of the salt of Formula I, q is +. In some embodiments of the salt of Formula I, q is -.

[0040] In some embodiments of the salt of formula I, p is 2+. In some embodiments of the salt of formula I, p is +. In some embodiments of the salt of formula I, p is 2-. In some embodiments of the salt of formula I, p is -.

[0041] In some embodiments of the salt of Formula I, g is 1. In some embodiments of the salt of Formula I, g is 2.

[0042] In some embodiments of the salt of Formula I, q is +, p is -, and g is 1. In some embodiments of the salt of Formula I, q is +, p is 2-, and g is 2. In some embodiments of the salt of Formula I, q is -, p is +, and g is 1. In some embodiments of the salt of Formula I, q is -, p is 2+, and g is 2.

[0043] In some embodiments of the salt of formula I, G is R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - and a diallylammonium group, where R 5 are independently H, straight or branched chain C 1-6 In some embodiments of the salt of formula I, G is selected from R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - , and (CH2=CH-CH2) i NR 4 (4-i) + where i is independently selected from 2 and 3, and where R 4 are independently H, straight or branched chain C 1-6 alkyl, where R 5 are independently H, straight or branched chain C 1-6 In some embodiments of the salt of formula I, G is selected from R 5 -C≡C-CO2 - and a diallylammonium group, where R 5 are independently H, straight or branched chain C 1-6 In some embodiments of the salt of formula I, G is selected from R 5 -C≡C-CO2 - and (CH2=CH-CH2)i NR (4-i) + where i is independently selected from 2 and 3, and where R 4 are independently H, straight or branched chain C 1-6 alkyl, where R 5 are independently H, straight or branched chain C 1-6 In some embodiments of the salt of formula I, G is selected from HC≡C-CO2. - , and (CH2=CH-CH2) i NH (4-i) + where i is independently selected from 2 and 3.

[0044] In some embodiments of the salt of formula I, q is + and G is a diallylammonium group. In some embodiments of the salt of formula I, q is + and G is (CH2=CH-CH2). i NR 4 (4-i) + where i is independently selected from 2 and 3, and where R 4 are independently H, straight or branched chain C 1-6 In some embodiments of the salt of Formula I, q is + and G is selected from (CH2=CH-CH2). i NH (4-i) + where i is independently selected from 2 and 3. In the embodiments described in this paragraph, preferably, p is - and g is 1.

[0045] In some embodiments of the salt of Formula I, q is - and G is R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - , R 5 -C≡C-SO2 - , R 5 -C≡CS(=O)S- , R 5 -C≡C-SO3 - , R 5 -C≡CS(=O)2S - where R 5 are independently H, straight or branched chain C 1-6 In some embodiments of the salt of Formula I, q is - and G is selected from R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - where R 5 are independently H, straight or branched chain C 1-6 In some embodiments of the salt of Formula I, q is - and G is selected from R 5 -C≡C-CO2 - where R 5 are independently H, straight or branched chain C 1-6 In the embodiments described in this paragraph, preferably, p is 2+ and g is 2.

[0046] In some embodiments of the salt of formula I, L is a linear C 1-10 alkyl, where one or more CH groups are independently -(CH-O-CH)-, -(CH-CH-O)-, -(O-CH-CH)-, C=O, -O-, -S-, -NH-, or -NR 1- where R 1 is a linear or branched chain C 1-6 In some embodiments of the salt of formula I, L is a straight chain C alkyl. 1-10 In some embodiments of the salt of formula I, L is a straight chain C alkyl, where one or more CH groups are independently replaced with -(CH-O-CH)-, -(CH-CH-O)-, -(O-CH-CH)-, C=O, -O-, or -S-. 1-10alkyl, where one or more CH groups are independently replaced by -(CH2-O-CH2)-, -(CH2-CH2-O)-, -(O-CH2-CH2)-, or -O-.

[0047] In some embodiments of the salt of formula I, A is NR 2 3 + , CO2 - , C(=O)S - , CS2 - where R 2 is independently in each occurrence H, straight or branched chain C 1-6 In some embodiments of the salt of formula I, p is + or 2+ and A is NR 2 3 + where R 2 is independently in each occurrence H, straight or branched chain C 1-6 In some embodiments of the salt of formula I, p is - or 2- and A is CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , and S(=O)2S - where R 2 is independently in each occurrence H, straight or branched chain C 1-6 In some embodiments of the salt of formula I, p is - or 2- and A is selected from CO2 - , C(=O)S - , CS2 - In some embodiments of the salt of formula I, p is - or 2- and A is CO2 - It is.

[0048] In some embodiments of the salt of formula I, E is NR 3 2. NR 3 3 + , CO2H, C(=O)SH, CS2H, CO2 - , C(=O)S - , CS2- where R 3 is independently in each occurrence H, straight or branched chain C 1-6 In some embodiments of the salt of formula I, E is selected from NR 3 2. NR 3 3 + , CO2H, CO2 - where R 3 is independently in each occurrence H, straight or branched chain C 1-6 is selected from alkyl.

[0049] In some embodiments of the salt of formula I, q is +; p is - or 2-; g is 1 or 2; G is a diallylammonium group; L is linear C 1-15 alkyl, where one or more CH groups are independently -(CH-O-CH)-, -(CH-CH-O)-, -(O-CH-CH)-, C=O, -O-, -S-, -NH-, or -NR 1 -, where R 1 is linear or branched C 1-6 is alkyl; A is CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , and S(=O)2S - Selected from; E is NR 3 2, CO2H, C(=O)SH, CS2H, SO2H, S(=O)SH, SO3H, S(=O)2SH, CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , S(=O)2S - where R 3is independently in each occurrence H, straight or branched chain C 1-6 alkyl; However, the overall charge of A and E is not zero, and the salt of formula I has an overall neutral charge.

[0050] In some embodiments of the salt of formula I, q is -; p is 2+ or +; g is 1 or 2; G is R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - , R 5 -C≡C-SO2 - , R 5 -C≡CS(=O)S - , R 5 -C≡C-SO3 - , R 5 -C≡CS(=O)2S - where R 5 are independently H, straight or branched chain C 1-6 alkyl; L is linear C 1-15 alkyl, where one or more CH groups are independently -(CH-O-CH)-, -(CH-CH-O)-, -(O-CH-CH)-, C=O, -O-, -S-, -NH-, or -NR 1 -, where R 1 is linear or branched C 1-6 is alkyl; A is NR 2 3 + where R 2 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; E is NR 3 2. NR 3 3 +, CO2H, C(=O)SH, CS2H, SO2H, S(=O)SH, SO3H, S(=O)SH, where R 3 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; However, the overall charge of A and E is not zero, and the salt of formula I has an overall neutral charge.

[0051] In some embodiments, the salt of the invention is of formula II: [ka] During the ceremony, q is + or -; p is 2+, +, -, or 2-; g is 1 or 2; G is R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - , R 5 -C≡C-SO2 - , R 5 -C≡CS(=O)S - , R 5 -C≡C-SO3 - , R 5 -C≡CS(=O)2S - , and (CH2=CH-CH2) i NR 4 (4-i) + where i is independently selected from 2 and 3, and where R 4 are independently H, straight or branched chain C 1-6 alkyl, where R 5 are independently H, straight or branched chain C 1-6 alkyl; A is NR 2 3 + , CO2 - , C(=O)S - , CS2 - , SO2- , S(=O)S - , SO3 - , S(=O)2S - where R 2 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; E is NR 3 2. NR 3 3 + , CO2H, C(=O)SH, CS2H, SO2H, S(=O)SH, SO3H, S(=O)2SH, CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , S(=O)2S - where R 3 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; M is O, S, NH, and NR 1 where R 1 is a linear or branched chain C 1-6 is alkyl; m and n are independently selected from 1, 2, and 3; x and y are independently selected from 0, 1, and 2; However, the overall charge of A and E is not zero, and the salt of formula II has an overall neutral charge.

[0052] In some embodiments of the salt of Formula II, q is +. In some embodiments of the salt of Formula II, q is -.

[0053] In some embodiments of the salt of formula II, p is 2+. In some embodiments of the salt of formula II, p is +. In some embodiments of the salt of formula II, p is 2-. In some embodiments of the salt of formula II, p is -.

[0054] In some embodiments of the salt of Formula II, g is 1. In some embodiments of the salt of Formula II, g is 2.

[0055] In some embodiments of the salt of Formula II, q is +, p is -, and g is 1. In some embodiments of the salt of Formula II, q is +, p is 2-, and g is 2. In some embodiments of the salt of Formula II, q is -, p is +, and g is 1. In some embodiments of the salt of Formula II, q is -, p is 2+, and g is 2.

[0056] In some embodiments of the salt of formula II, G is R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - , and (CH2=CH-CH2) i NR 4 (4-i) + where i is independently selected from 2 and 3, and where R 4 are independently H, straight or branched chain C 1-6 alkyl, where R 5 are independently H, straight or branched chain C 1-6 In some embodiments of the salt of formula II, G is selected from R 5 -C≡C-CO2 - and (CH2=CH-CH2) i NR 4 (4-i) + where i is independently selected from 2 and 3, and where R 4 are independently H, straight or branched chain C 1-6 alkyl, where R 5 are independently H, straight or branched chain C 1-6 In some embodiments of the salt of formula II, G is selected from R 5 -C≡C-CO2- and (CH2=CH-CH2) i NH (4-i) + where i is independently selected from 2 and 3, and where R 5 are independently H, straight or branched chain C 1-6 is selected from alkyl.

[0057] In some embodiments of the salt of Formula II, q is + and G is (CH2=CH-CH2). i NR 4 (4-i) + where i is independently selected from 2 and 3, and where R 4 are independently H, straight or branched chain C 1-6 In some embodiments of the salt of Formula II, q is + and G is selected from (CH2=CH-CH2). i NH (4-i) + where i is independently selected from 2 and 3. In the embodiments described in this paragraph, preferably, p is - and g is 1.

[0058] In some embodiments of the salt of Formula II, q is - and G is R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - , R 5 -C≡C-SO2 - , R 5 -C≡CS(=O)S - , R 5 -C≡C-SO3 - , R 5 -C≡CS(=O)2S - where R 5 are independently H, straight or branched chain C 1-6 In some embodiments of the salt of Formula II, q is - and G is selected from R 5 -C≡C-CO2- , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - where R 5 are independently H, straight or branched chain C 1-6 In some embodiments of the salt of Formula II, q is - and G is selected from R 5 -C≡C-CO2 - where R 5 are independently H, straight or branched chain C 1-6 In the embodiments described in this paragraph, preferably, p is 2+ and g is 2.

[0059] In some embodiments of the salt of Formula II, m and n are both selected from 1, 2, and 3. In some embodiments of the salt of Formula II, m and n are 1. In some embodiments of the salt of Formula II, m and n are 2. In some embodiments of the salt of Formula II, m and n are 3.

[0060] In some embodiments of the salt of Formula II, x and y are both selected from 0, 1, and 2. In some embodiments of the salt of Formula II, x and y are both 0. In some embodiments of the salt of Formula II, x and y are both 1. In some embodiments of the salt of Formula II, x and y are both 2. In some embodiments of the salt of Formula II, x is 0 and y is 1.

[0061] In some embodiments of the salt of formula II, A is NR 2 3 + , CO2 - , C(=O)S - , CS2 - where R 2 is independently in each occurrence H, straight chain or branched C 1-6 In some embodiments of the salt of Formula II, p is + or 2+ and A is NR2 3 + where R 2 is independently in each occurrence H, straight or branched chain C 1-6 In some embodiments of the salt of formula II, p is - or 2- and A is selected from CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , and S(=O)2S - where R 2 is independently in each occurrence H, straight or branched chain C 1-6 In some embodiments of the salt of formula II, p is - or 2- and A is selected from CO2 - , C(=O)S - , CS2 - In some embodiments of the salt of formula II, p is - or 2- and A is CO2 - It is.

[0062] In some embodiments of the salt of formula II, E is NR 3 2. NR 3 3 + , CO2H, C(=O)SH, CS2H, CO2 - , C(=O)S - , CS2 - where R 3 is independently in each occurrence H, straight or branched chain C 1-6 In some embodiments of the salt of formula II, E is selected from NR 3 2. NR 3 3 + , CO2H, CO2 - where R 3 is independently in each occurrence H, straight or branched chain C 1-6 is selected from alkyl.

[0063] In some embodiments of the salt of formula II, q is +; p is - or 2-; g is 1 or 2; G is (CH2=CH-CH2) i NR 4 (4-i) + where i is independently selected from 2 and 3, and where R 4 are independently H, straight or branched chain C 1-6 alkyl; A is CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , S(=O)2S - where R 2 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; E is NR 3 2, CO2H, C(=O)SH, CS2H, SO2H, S(=O)SH, SO3H, S(=O)2SH, CO2 - , C(=O)S - , CS2 - , SO2 - , S(=O)S - , SO3 - , S(=O)2S - wherein R3 is independently selected at each occurrence from H, straight or branched chain C 1-6 alkyl; M is O, S, NH, and NR 1 where R 1 is a linear or branched chain C 1-6 is alkyl; m and n are independently selected from 1, 2, and 3; x and y are independently selected from 0, 1, and 2; However, the overall charge of A and E is not zero, and the salt of formula II has an overall neutral charge.

[0064] In some embodiments of the salt of formula II, q is -; p is 2+ or +; g is 1 or 2; G is R 5 -C≡C-CO2 - , R 5 -C≡CC(=O)S - , R 5 -C≡C-CS2 - , R 5 -C≡C-SO2 - , R 5 -C≡CS(=O)S - , R 5 -C≡C-SO3 - , R 5 -C≡CS(=O)2S - , where R 5 are independently H, straight or branched chain C 1-6 alkyl; A is NR 2 3 + where R 2 is independently in each occurrence H, straight or branched chain C 1-6 alkyl, E is NR 3 2. NR 3 3 + , CO2H, C(=O)SH, CS2H, SO2H, S(=O)SH, SO3H, S(=O)SH, where R 3 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; M is O, S, NH, and NR 1 where R 1 is a linear or branched chain C 1-6 is alkyl; m and n are independently selected from 1, 2, and 3; x and y are independently selected from 0, 1, and 2; However, the overall charge of A and E is not zero, and the salt of formula II has an overall neutral charge.

[0065] In some embodiments of any of the salts disclosed herein, the diallylammonium group is a moiety of formula d1 or d2: [ka] In the formula, R 4 is independently in each occurrence H, straight or branched chain C 1-6 is selected from alkyl.

[0066] In some embodiments of any of the salts disclosed herein, the diallyl ammonium group is of formula d1 or d2, where R 4 is H.

[0067] In some embodiments of any of the salts disclosed herein, the diallyl ammonium group is a moiety of formula d1. In some embodiments of any of the salts disclosed herein, the diallyl ammonium group is a moiety of formula d2.

[0068] In some embodiments of the salts disclosed herein, the ion containing the diallylammonium group is (CH2=CHCH2)2NH2 + It is.

[0069] In some embodiments, the salt of the invention is of formula III: [ka] During the ceremony, M is O, S and NR 6 where R 6 is H, straight or branched chain C 1-6 alkyl; R 5 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; m and n are independently selected from 1, 2, and 3; x and y are independently selected from 0, 1, and 2.

[0070] In some embodiments of the salt of Formula III, M is O. In some embodiments of the salt of Formula III, M is S. In some embodiments of the salt of Formula III, M is NR 6 where R 6 is H, straight or branched chain C 1-6 is selected from alkyl.

[0071] In some embodiments of the salt of formula III, R 5 is H. In some embodiments of the salt of formula III, R 5 is a linear or branched chain C 1-6 It is an alkyl.

[0072] In some embodiments of the salt of Formula III, x and y are independently selected from 0 and 1. In some embodiments of the salt of Formula III, x and y are selected from 0, 1, and 2. In some embodiments of the salt of Formula III, x and y are selected from 0 and 1. In some embodiments of the salt of Formula III, x and y are 0. In some embodiments of the salt of Formula III, x and y are 1. In some embodiments of the salt of Formula III, x is 0 and y is 1.

[0073] In some embodiments of the salt of Formula III, m and n are independently selected from 2 and 3. In some embodiments of the salt of Formula III, m and n are selected from 1, 2, and 3. In some embodiments of the salt of Formula III, m and n are selected from 2 and 3. In some embodiments of the salt of Formula III, m and n are 2. In some embodiments of the salt of Formula III, m and n are 3.

[0074] In some embodiments of the salt of Formula III, m and n are 2, and x and y are 0. In some embodiments of the salt of Formula III, m and n are 3, and x and y are 1. In some embodiments of the salt of Formula III, m and n are 2, x is 0, and y is 1. In some embodiments of the salt of Formula III, m and n are 3, x is 0, and y is 1.

[0075] In some embodiments of the salt of formula III, M is O, m and n are 2, and x and y are 0. In some embodiments of the salt of formula III, M is O, m and n are 3, and x and y are 1. In some embodiments of the salt of formula III, M is O, m and n are 2, x is 0, and y is 1. In some embodiments of the salt of formula III, M is O, m and n are 3, x is 0, and y is 1.

[0076] In some embodiments, the salt of the invention is of formula IV: [ka] During the ceremony, M is O, S, and NR 6 where R 6 is H, straight or branched chain C 1-6 alkyl; R 4 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; m and n are independently selected from 1, 2, and 3; x and y are independently selected from 0, 1, and 2.

[0077] In some embodiments of the salt of Formula III, M is O. In some embodiments of the salt of Formula III, M is S. In some embodiments of the salt of Formula III, M is NR 6 where R6 is H, straight or branched chain C 1-6 is selected from alkyl.

[0078] In some embodiments of the salt of formula III, R 4 is H at each occurrence. In some embodiments of the salt of formula III, R 4 In each occurrence, 1-6 It is alkyl, for example methyl, ethyl or n-propyl, especially methyl.

[0079] In some embodiments of the salt of Formula IV, m and n are independently selected from 1 and 2. In some embodiments of the salt of Formula IV, m and n are selected from 1, 2, and 3. In some embodiments of the salt of Formula IV, m and n are selected from 1 and 2. In some embodiments of the salt of Formula IV, m and n are 1. In some embodiments of the salt of Formula IV, m and n are 2.

[0080] In some embodiments of the salt of Formula IV, x and y are independently selected from 0 and 1. In some embodiments of the salt of Formula IV, x and y are selected from 0, 1, and 2. In some embodiments of the salt of Formula IV, x and y are selected from 0 and 1. In some embodiments of the salt of Formula IV, x and y are 0. In some embodiments of the salt of Formula IV, x and y are 1. In some embodiments of the salt of Formula IV, x is 0 and y is 1.

[0081] In some embodiments of the salt of Formula IV, m and n are 1 and x and y are 1. In some embodiments of the salt of Formula IV, m and n are 1 and x and y are 0. In some embodiments of the salt of Formula IV, m and n are 2 and x and y are 1.

[0082] In some embodiments of the salt of formula IV, M is O, m and n are 1, and x and y are 1. In some embodiments of the salt of formula IV, M is O, m and n are 1, and x and y are 0. In some embodiments of the salt of formula IV, M is O, m and n are 2, and x and y are 1.

[0083] In more specific embodiments, the present disclosure relates to the specific examples disclosed in Table 1.

[0084] [Table 1]

[0085] The salts of the present disclosure may contain one or more asymmetric centers in the molecule. It should be understood that salts without designation of stereochemistry include all optical isomers (e.g., diastereomers, enantiomers, etc.) in pure or substantially pure form, and also mixtures thereof (e.g., racemic mixtures, or mixtures enriched in one enantiomer). Methods for preparing such optically active forms are well known in the art (e.g., by resolution of racemates by recrystallization techniques, synthesis from optically active starting materials, chiral synthesis, chromatographic separation using chiral stationary phases, and other methods).

[0086] The salts may be isotopically labeled compounds, e.g., compounds containing various isotopes of hydrogen, carbon, nitrogen, and oxygen. The disclosed salts may exist in tautomeric forms and mixtures, with individual tautomers being contemplated. Additionally, some salts may exhibit polymorphism.

[0087] The salts of the present disclosure can exist in solid, i.e. crystalline (e.g. polymorphs, i.e. different crystal structures with the same chemical composition but different packing, geometric arrangement), or in amorphous form (optionally as solvates), or in liquid form. In the solid state, they may exist alone or as mixtures thereof. In crystalline solvates, the solvent molecules are incorporated into the crystal lattice during crystallization. Solvate formers can include, but are not limited to, non-aqueous solvents such as ethanol, isopropanol, DMSO, acetic acid, ethanolamine, or ethyl acetate, or aqueous solvents such as water (also called "hydrates"). For example, different polymorphs can be produced by changing or adjusting the reaction conditions or reagents.

[0088] In a further aspect, the present disclosure also provides methods for preparing the salts of Formulas I-IV of the present disclosure.

[0089] In yet another aspect, the present disclosure further provides a cosmetic formulation comprising one or more of the salts of the present disclosure in an effective amount and one or more pharma- ceutically acceptable carriers and / or excipients (also called diluents).Excipients are acceptable in the sense that they are compatible with other ingredients of the formulation and are not harmful to the recipient.As used herein, the term "effective amount" refers to the amount of the salt of the present disclosure (as such or in the form of a cosmetic formulation) that is effective to cause the desired effect of hair restoration.

[0090] Generally, the pH of a cosmetic preparation is 3.5 to 6, particularly 4 to 5, at 20° C. The pH can be adjusted using, for example, lactic acid, citric acid, or the like.

[0091] Typically, the concentration of the salts disclosed herein is from 0.01% to 5% by weight of the cosmetic formulation, such as from 2% to 4% by weight. In some embodiments, the concentration of the salts disclosed herein is from 50 to 130 mmol per liter of cosmetic formulation, particularly from 80 to 100 mmol per liter.

[0092] In some embodiments, the cosmetic formulation comprises a solubilizer. The concentration of the solubilizer may be, for example, 5% to 20% by weight of the cosmetic formulation, particularly 10% to 20% by weight, for example 15% to 20% by weight.

[0093] In some embodiments, the cosmetic formulation comprises phenoxyethanol at a concentration of 0.1% to 1.7%, particularly 0.7% to 1.1%, for example 0.9%, by weight of the cosmetic formulation.

[0094] In some embodiments, the cosmetic formulation comprises ethylhexylglycerin at a concentration of 0.01% to 0.2%, particularly 0.08% to 0.12%, for example 0.1%, by weight of the cosmetic formulation.

[0095] As used herein, the phrase "pharmaceutically acceptable carrier" refers to a pharma- ceutically acceptable material, composition, or vehicle, such as a liquid or solid filler, diluent, excipient, manufacturing aid (e.g., lubricants, magnesium talc, calcium or zinc stearate, or stearic acid), or solvent encapsulating material that is involved in carrying or transporting the subject salt or compound from one organ or body part to another. Each carrier must be "acceptable" in the sense of being compatible with the other ingredients of the formulation and not deleterious to the subject. Some examples of materials which can serve as pharma- ceutically acceptable carriers include: (1) sugars, such as lactose, glucose, and sucrose; (2) starches, such as corn starch and potato starch; (3) cellulose and its derivatives, such as sodium carboxymethylcellulose, ethylcellulose, and cellulose acetate; (4) powdered tragacanth; (5) malt; (6) gelatin; (7) talc; (8) excipients, such as cocoa butter and suppository wax; (9) oils, such as peanut oil, cottonseed oil, safflower oil, sesame oil, olive oil, corn oil, and soybean oil; (10) propylene glycol. (11) polyols, such as glycerin, sorbitol, mannitol, and polyethylene glycol; (12) esters, such as ethyl oleate and ethyl laurate; (13) agar; (14) buffers, such as magnesium hydroxide and aluminum hydroxide; (15) alginic acid; (16) pyrogen-free water; (17) isotonic saline; (18) Ringer's solution; (19) ethyl alcohol; (20) pH buffers; (21) polyesters, polycarbonates, and / or polyanhydrides; and (22) other non-toxic compatible substances used in cosmetic formulations.

[0096] Such compositions may contain additional components commonly used in cosmetic formulations, such as wetting agents, emulsifiers and lubricants, such as sodium lauryl sulfate and magnesium stearate, as well as coloring agents, release agents, coating agents, sweeteners, flavorings and fragrances, preservatives and antioxidants, pH modifiers, bulking agents, and additional active agents.Examples of pharmaceutically acceptable antioxidants include (1) water-soluble antioxidants such as ascorbic acid, cysteine ​​hydrochloride, sodium bisulfate, sodium metabisulfite, sodium sulfite; (2) oil-soluble antioxidants such as ascorbyl palmitate, butyl hydroxyanisole (BHA), butyl hydroxytoluene (BHT), lecithin, propyl gallate, α-tocopherol; and (3) metal chelators such as citric acid, ethylenediaminetetraacetic acid (EDTA), sorbitol, tartaric acid, phosphoric acid.

[0097] Such compositions can be prepared by any method known in the art, for example, by associating the active ingredient with one or more carriers and / or excipients.Various compositions and examples of carriers and / or excipients are well known to those skilled in the art and are described in detail in, for example, Remington: The Science and Practice of Pharmacy. Pharmaceutical Press, 2013; Rowe, Sheskey, Quinn: Handbook of Pharmaceutical Excipients. Pharmaceutical Press, 2009.The excipients that can be used in the manufacture of cosmetic preparations can include one or more of buffers, stabilizers, surfactants, wetting agents, lubricants, emulsifiers, suspending agents, preservatives, antioxidants, opaquing agents, glidants, processing aids, colorants, sweeteners, fragrances, flavorings, diluents, and other known additives to provide a composition or formulation suitable for the selected administration.

[0098] The cosmetic formulation of the present disclosure may be in any suitable form.In some embodiments, such suitable forms include, but are not limited to, liquids, such as low to medium viscosity liquids, such as lotions, emulsions, mousses, sprays, gels, creams, ointments, pastes, etc.Suitable excipients such as those listed above are included or excluded from skin formulations depending on the form of use of the formulation (e.g., lotions, gels, ointments, or creams).

[0099] The liquid forms of the salts of the present disclosure include pharma- ceutically acceptable emulsions, microemulsions, solutions, suspensions, syrups, and elixirs.In addition to the active ingredient, the liquid forms can contain inert diluents commonly used in the art, such as water or other solvents, solubilizers and emulsifiers, such as ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylene glycol, oils (especially cottonseed oil, peanut oil, corn oil, germ oil, olive oil, castor oil, and sesame oil), glycerol, tetrahydrofuryl alcohol, polyethylene glycol, and fatty acid esters of sorbitan, and mixtures thereof.In the form of suspensions, the salts can contain suspending agents, such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar-agar, and tragacanth, and mixtures thereof.

[0100] In the form of sprays, ointments, pastes, creams, lotions, gels, solutions, the salts or compounds can be mixed under sterile conditions with a pharma- ceutically acceptable carrier and, if necessary, with any preservatives, buffers, or propellants. Such ointments, pastes, creams, and gels can contain, in addition to the salts of the invention, excipients such as animal and vegetable fats, oils, waxes, paraffins, starches, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonite, silicic acid, talc, and zinc oxide, or mixtures thereof.

[0101] In the form of powders and sprays, the salts of the present disclosure can contain excipients such as lactose, talc, silicic acid, aluminum hydroxide, calcium silicate, and polyamide powder, or mixtures of these substances. Sprays can further contain common propellants such as chlorofluorohydrocarbons and volatile unsubstituted hydrocarbons such as butane, propane, etc.

[0102] In some embodiments, the cosmetic formulation is a hair care product, including products in the form of shampoos, conditioners, hair masks, hair rinses, hair sprays, hair foams, hair mousses, hair gels, hair tonics, and the like.

[0103] It will be understood that all contemplated compositions and preparations must be stable under the conditions of manufacture and storage and preserved against the contaminating action of microorganisms, such as bacteria and fungi.

[0104] The amount of the salt of the present disclosure in the cosmetic formulation of the present disclosure can be adjusted to obtain an amount of the salt of the present disclosure that is effective to achieve the desired cosmetic response for a particular person, composition, and method of administration without being harmful to the person. The amount selected will depend on a variety of factors, including the nature of the particular salt of the present disclosure used, the route of administration, the time of administration, the duration of treatment, other compounds, salts, and / or materials used in combination with the particular salt, the age, sex, weight, condition, general health, and previous medical history of the person receiving the treatment, and similar factors well known in the medical arts.

[0105] Generally, a suitable amount of the salt of the present disclosure is that amount of salt that is the minimum amount effective to cause the desired effect. Such an effective dose generally depends on the factors mentioned above. In the form of a shampoo, the amount of the cosmetic preparation applied in one treatment can be, for example, 1 g to 10 g. In the form of a conditioner and / or hair mask, the amount of the cosmetic preparation applied in one treatment can be, for example, 1 g to 10 g. In the form of a leave-on conditioner or leave-on mask, the amount of the cosmetic preparation applied in one treatment can be, for example, 0.1 g to 7 g.

[0106] All of the salts, compositions, formulations and / or methods disclosed and claimed herein can be made and carried out without undue experimentation in light of this disclosure.It is clear to those skilled in the art that those variations can be applied to this disclosure without departing from the scope of this disclosure.The examples provided herein are intended to be illustrative and are not exhaustive.Therefore, the examples shown should not be considered as limiting this disclosure in any way. EXAMPLES

[0107] material: N-Cbz-cysteine ​​was obtained by reduction of its cysteine ​​counterpart by methods known in the literature. Adv. Syn. Catal., 2020, 362, 5093-5104. DOI: 10.1002 / adsc.202000716. "OLAPLEX® N O "Olaplex 1.0 Intensive Bond Building Hair Treatment" is a commercial product that contains an active agent, water, phenoxyethanol, and sodium benzoate. The active agent is hereinafter referred to as "Olaplex active agent."

[0108] Example 1: Synthesis of Olaplex Active Agent The active agent used as a reference compound in Example 8, "Olaplex active agent," has the following structure: [ka] It was synthesized by reacting two equivalents of the corresponding acid with one equivalent of the corresponding diamine.

[0109] Example 2: Synthesis of salt 15 (SPC-TB-0015) [ka] (a) SPC-TB-0015 To a solution of 2,2'-oxybis(ethan-1-amine) (100 mg, 1.0 eq, 0.96 mmol) in DCM (1.92 mL) was added propiolic acid (134 mg, 2.0 eq, 1.92 mmol). After 2 h reaction time, the solvent was concentrated to give the resulting salt (235 mg, quant.) as an orange oil. 1 H NMR(400MHz, DMSO)δ8.29(m, 6H), 3.59(dd, J=5.6Hz, 4.4Hz, 4H), 3.16(m, 2H), 2.97(dd, J=5.6Hz, 4.4Hz, 4H).

[0110] Example 3: Synthesis of salt 16 (SPC-TB-0016) [ka] (a) SPC-TB-0016 To a solution of 3,3'-((oxybis(ethane-2,1-diyl))bis(oxy))bis(propan-1-amine) (500 mg, 1.0 eq, 2.27 mmol) in DCM (4.54 mL) was added propiolic acid (318 mg, 2.0 eq, 4.53 mmol). After 2 h reaction time, the solvent was concentrated to give the resulting salt (818 mg, quant.) as an orange oil. 1 H NMR(400MHz, DMSO)δ8.08(s, 6H), 3.55-3.42(m, 12H), 2.99(s, 2H), 2.87-2.76(m, 4H), 1.78(p, J=8.0, 6.2Hz, 4H).

[0111] Example 4: Synthesis of salt 17 (SPC-TB-0017) [ka] (a) SPC-TB-0017 To a solution of 2,2'-((oxybis(ethane-2,1-diyl))bis(oxy))diacetic acid (5.000 g, 1 Eq, 22.50 mmol) dissolved in MeCN (24.46 ml) was added diallylamine (2.186 g, 2.78 mL, 1 Eq, 22.50 mmol) slowly at room temperature. The solution was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure to give the resulting salt (7.179 g, 22.48 mmol, 99.90%) as a yellow oil. 1 H NMR(400MHz, DMSO)δ9.03(s, 2H), 5.87(ddt, J=16.8, 10.4, 6.3Hz, 2H), 5.35-5.17(m, 4H), 3.88(s, J=1.5Hz, 4H), 3.54(dddt, J=7.8, 5.8, 4.2, 2.1Hz, 8H), 3.30(d, J=20.1Hz, 5H).

[0112] Example 5: Synthesis of salt 18 (SPC-TB-0018) [ka] (a) SPC-TB-0018 At the 15g scale, the procedure was modified: 2,2'-Oxydiacetic acid (15.0 g, 1 Eq, 112 mmol) was suspended in MeCN (122 mL) at room temperature. Diallylamine (10.9 g, 13.8 mL, 1 Eq, 112 mmol) was then added dropwise (at this point everything was dissolved) and the solution was stirred at room temperature for 1 h. The solvent was concentrated to give the resulting salt as an off-white solid (25.9 g, quant.). 1 H NMR(400MHz, DMSO)δ5.35(m, 2H), 5.40(m, 4H), 3.93(s, 4H), 3.53(d, J=2.7Hz, 4H).

[0113] Example 6: Synthesis of salt 19 (SPC-TB-0019) [ka] (a) SPC-TB-0019 To a solution of 3,3'-((oxybis(ethane-2,1-diyl))bis(oxy))dipropionic acid (400 mg, 1.0 eq., 1.60 mmol) in DCM (16.0 mL) was added diallylamine (311 mg, 2.0 eq., 3.20 mmol). After 2 h reaction time, the solvent was concentrated to give the resulting salt as a colorless oil (580 mg, quant.). 1 H NMR(400MHz, DMSO)δ5.82(m, 2H), 5.12(m, 4H), 3.59(t, J=6.4Hz, 4H), 3.15(m, 4H), 2.42(t, J=6.4Hz, 4H).

[0114] Example 7: Synthesis of salt 20 (SPC-TB-0020) [ka] (a) SPC-TB-0020 To a solution of 2,2'-(ethane-1,2-diylbis(oxy))bis(ethan-1-amine) (5.00 g, 1.00 Eq, 34.0 mmol) in DCM (14.0 mL) at 0° C. was added propiolic acid (4.20 mL, 2.00 Eq, 67.0 mmol) in DCM (14.0 mL) pre-cooled to 0° C. CAUTION: Very exothermic reaction, add very slowly. The reaction mixture was stirred at 0° C. for 15 min and allowed to warm to room temperature over 1 h. Concentration under reduced pressure afforded an orange oil (quantitative yield). 1 H NMR(400MHz, DMSO)δ3.63-3.56(m, 8H), 3.04(s, 2H), 2.95(t, J=5.4Hz, 4H).

[0115] Example 8: Thiol recombination General Procedure The compound to be tested (1 eq) was dissolved in an aqueous medium (0.02 M) and 4 eq of cysteine ​​reagent (N-Cbz-cysteine) was added. Phosphate buffer (pH=5.4) was used as the aqueous medium.

[0116] To make phosphate buffer, solutions of 0.1 M citric acid (using citric acid monohydrate) and 0.2 M Na2HPO4 (using Na2HPO4 or Na2HPO4·2H2O) were prepared in the following ratio: 44.25 mL / 55.75 mL = mL 0.1 M citric acid / mL 0.2 M Na2HPO4 and mixed to obtain a buffer with pH = 5.4.

[0117] The tests were carried out in LC-MS vials or small glass vials at ambient temperature of 30°C with stirring by a small magnetic stirrer. The reactions were carried out under normal atmosphere. The reactions were monitored by LC-MS. The reaction scale was 4-10 mg of the test compound. To calculate the conversion to the product, the ratios between the cysteine ​​reagent, each mono-adduct (mono), and the bis-adduct (bis) were compared as shown in the following scheme.

[0118] The compounds tested show enhanced reactivity with cysteine ​​derivatives compared to the Olaplex active agent. [ka]

[0119] [Table 2]

Claims

1. A salt of formula I. 【Chemical 1】 (In the formula, q is + or −; p is 2+, +, −, or 2−; g is 1 or 2; G is R 5 -C≡C-CO 2 - , R 5 -C≡C-C(=O)S - , R 5 -C≡C-CS 2 - , R 5 -C≡C-SO 2 - , R 5 -C≡C-S(=O)S - , R 5 -C≡C-SO 3 - , R 5 -C≡CS(=O) 2 S - and a diallylammonium group, wherein R 5 are independently H, straight or branched chain C 1-6 alkyl; L is a linear C 1-15 alkyl, where one or more CH 2 The groups are independently —(CH 2 -O-CH 2 ) -, -(CH 2 -CH 2 -O)-, -(O-CH 2 -CH 2 )-, C=O, -O-, -S-, -NH-, or -NR 1 - is substituted with R 1 is a straight or branched chain C 1-6 is alkyl; A is NR 2 3 + , CO 2 - , C(=O)S - , C.S. 2 - , S.O. 2 - , S(=O)S - , S.O. 3 - , and S(=O) 2 S - where R 2 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; E is NR 3 2 , N.R. 3 3 + , CO 2 H, C(=O)SH, CS 2 H, SO 2 H, S (=O) SH, SO 3 H, S(=O) 2 S.H., C.O. 2 - , C(=O)S - , C.S. 2 - , S.O. 2 - , S(=O)S - , S.O. 3 - , S(=O) 2 S - where R 3 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; However, the overall charge of A and E is not 0, and the salt of formula I has an overall neutral charge.

2. 2. The salt of claim 1 having formula II. 【Chemistry 2】 (In the formula, q is + or −; p is 2+, +, −, or 2−; g is 1 or 2; G is R 5 -C≡C-CO 2 - , R 5 -C≡C-C(=O)S - , R 5 -C≡C-CS 2 - , R 5 -C≡C-SO 2 - , R 5 -C≡C-S(=O)S - , R 5 -C≡C-SO 3 - , R 5 -C≡CS(=O) 2 S - where R 5 are independently H, straight or branched chain C 1-6 Alkyl, and (CH 2 =CH-CH 2 ) i NR 4 (4-i) + where i is independently selected from 2 and 3, and where R 4 are independently H, straight or branched chain C 1-6 alkyl; A is NR 2 3 + , CO 2 - , C(=O)S - , C.S. 2 - , S.O. 2 - , S(=O)S - , S.O. 3 - , S(=O) 2 S - where R 2 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; E is NR 3 2 , N.R. 3 3 + , CO 2 H, C(=O)SH, CS 2 H, SO 2 H, S (=O) SH, SO 3 H, S(=O) 2 S.H., C.O. 2 - , C(=O)S - , C.S. 2 - , S.O. 2 - , S(=O)S - , S.O. 3 - , S(=O) 2 S - where R 3 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; M is O, S, NH, and NR 1 where R 1 is a linear or branched chain C 1-6 is alkyl; m and n are independently selected from 1, 2, and 3; x and y are independently selected from 0, 1, and 2; However, the overall charge of A and E is not zero, and the salt of Formula I has an overall neutral charge.

3. 2. The salt of claim 1, wherein the diallylammonium group is a moiety of formula d1 or d2: 【Chemistry 3】 (In the formula, R 4 is independently in each occurrence H, straight or branched chain C 1-6 alkyl.)

4. 2. The salt of claim 1 having formula III: 【Chemistry 4】 (In the formula, M is O, S and NR 6 where R 6 is H, straight or branched chain C 1-6 alkyl; R 5 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; m and n are independently selected from 1, 2, and 3; x and y are independently selected from 0, 1, and 2.

5. R 5 The salt of claim 4, wherein is H and M is O.

6. 5. The salt of claim 4, wherein m and n are independently selected from 2 or 3.

7. 2. The salt of claim 1 having formula IV: 【Chemistry 5】 (In the formula, M is O, S, and NR 6 where R 6 is H, straight or branched chain C 1-6 alkyl; R 4 is independently in each occurrence H, straight or branched chain C 1-6 alkyl; m and n are independently selected from 1, 2, and 3; x and y are independently selected from 0, 1, and 2.

8. R 4 The salt of claim 7, wherein is H and M is O.

9. 8. The salt of claim 7, wherein m and n are independently selected from 1 and 2.

10. 3. The salt of claim 2, wherein m is equal to n and x is equal to y.

11. Cosmetic preparations comprising at least one salt according to any one of claims 1 to 10.

12. 12. The cosmetic formulation of claim 11, further comprising at least one cosmetic additive selected from the group consisting of surfactants, oil components, emulsifiers, pearlescent waxes, consistency improvers, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithin, phospholipids, UV protection agents, moisturizers, biogenic agents, antioxidants, deodorants, antiperspirants, antidandruff agents, film formers, bulking agents, insect repellents, self-tanning agents, tyrosine inhibitors (bleaching agents), hydrotropes, solubilizers, preservatives, fragrance oils and dyes, and mixtures thereof.

13. The cosmetic formulation of claim 11 further comprising a carrier.

14. The cosmetic formulation of claim 13, wherein the carrier is selected from water, C(2-6)-alcohols, C(1-10) polyols, and oil components.

15. Use of a salt according to any one of claims 1 to 10 for the manufacture of a cosmetic preparation.

16. The use according to claim 15, wherein the cosmetic preparation is a hair care product.

17. A method for treating keratinous materials, comprising the step of applying a salt according to any one of claims 1 to 10 to said keratinous materials.

18. A method for treating keratinous materials, comprising the step of applying a cosmetic formulation according to claim 11 to said keratinous materials.

Images