Cosmetic salts
Thiol-reactive agents address the issue of hair damage by modifying and crosslinking thiol moieties in keratin, restoring disulfide bridges and improving hair strength and texture.
Patent Information
- Application Number
- PCT/EP2024/070613
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-07-19
- Filing Date
- 2024-07-19
- Publication Date
- 2025-01-23
AI Technical Summary
Existing hair treatment processes often result in damage to hair, particularly due to chemical and physical treatments that break disulfide bridges in keratin, leading to weakened hair structure.
Development of thiol-reactive agents that modify, shield, and crosslink thiol moieties in keratin, forming thiol-adducts and restoring disulfide bridges to enhance hair quality, strength, and texture.
The use of these thiol-reactive agents effectively shields and crosslinks thiol moieties, thereby repairing and improving hair quality by reducing damage and enhancing strength and texture.
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Figure EP2024070613_23012025_PF_FP_ABST
Abstract
Description
[0001] P26767PC00 19.07.2024 1 / 62 Cosmetic salts Field of the Disclosure The present disclosure relates to salts and cosmetic preparations thereof and their use as hair care products. Further disclosed is a method for treatment of keratin materials, such as hair. Background of the Disclosure Human hair has a highly organized but complex structure. It is composed of the hair follicle, which is embedded in the skin, and hair shaft, which extends out of the skin. Hair is typically 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 that is made of packed cells and / or hollow spaces. A large part of the mass of the human hair is composed of fibrous structures called macrofibrils, each one consists of microfibrils held together by matrix pro- teins. Human hair consists of 65–95 wt% proteins, predominantly keratin which is a fi- brous, helicoidal protein particularly rich in the amino acid cysteine, whose thiol groups may form disulfide crosslinks adding rigidity and resistance to the entire hair structure. There are various treatments for hair, such as bleaching, dyeing, straightening and perma- nent waving, during which hair may become overprocessed or damaged due to the chem- icals needed to effect the change desired. For example, some known hair straightening processes consist of treatment with alkaline straightener. The high pH (9.0–14.0) causes the hair to swell, which allows the alkaline agent to penetrate into the hair fibers, where it reacts with keratin and causes breaking and rearranging of the disulfide bridges present in keratin, allowing hair to be stretched. In addition to chemically caused damage, physical treatments such as frequent and / or high heat or environmental exposure may produce changes in hair texture and lead to further often permanent damage. P26767PC00 19.07.2024 2 / 62 Summary of the Disclosure It would be highly desirable to be able to avoid, minimize, alleviate or repair any such dam- age that occurs during those hair treatment processes and in particular to shield free thiol moieties from further degradation and additional damage by forming thiol adducts and / or disulfide bridges to regain and improve hair quality, strength and texture. It is an object of the present disclosure to advance the state of the art of hair repair. It is a further object of the present disclosure to provide salts and preparations for use as hair care products, which are able to modify, preferably crosslink or shield thiol moieties. The thiol moieties to be modified may, for example, have been formed by cleavage of disulfide bridges as a result of physical or chemical hair treatments. It is a further object of the pre- sent disclosure to enhance the formation of thiol adducts and / or restoration of disulfide bridges using the inventive linkers in hair. Applicants have developed thiol-reactive agents, which are capable of modifying, prefer- ably shielding and / or crosslinking thiol moieties, thus forming thiol-adducts and / or disul- fide bridges. The thiol moieties to be modified may, for example, result from prior cleavage of disulfide bridges, e.g. as a result of physical or chemical hair treatments. By shielding and / or crosslinking the thiol moieties, the thiol-reactive agents disclosed herein effectively form thiol-adducts and / or restoration of disulfide bridges. The present disclosure is in a first aspect directed to salts of formula I wherein q is + or –; p is 2+, +, – or 2–; P26767PC00 19.07.2024 3 / 62 g is 1 or 2; G is selected from R5-C≡C-(CH2)v-CO2–, R5-C≡C-(CH2)v-C(=O)S–, R5-C≡C-(CH2)v- CS2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is selected from 0, 1, 2, 3 or 4, wherein i is selected from 1, 2 and 3, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; L is straight-chain C2-4 alkyl, wherein one or more CH2 groups may independently be substituted by straight-chain or branched C1-6 alkyl, -OH, =O, -NH2, -NHMe, -NMe2; A is selected from NR23+, CO2–, C(=O)S–, CS2–, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; E is selected from NR32, NR33+, CO2H, C(=O)SH, CS2H, CO2–, C(=O)S–, CS2–, wherein, for each occurrence independently, R3is selected from H, linear or branched C1- 6 alkyl; with the proviso that the overall charge of A and E is not 0 and with the proviso that the salt of formula I is overall neutral in charge. In some embodiments of a salt of formula I, L is a straight-chain C2-3 alkyl, wherein one or more CH2 groups may independently be substituted by straight-chain or branched C1-4 al- kyl, -OH. In some embodiments, the present disclosure is directed towards a salt of formula II wherein q is + or –; P26767PC00 19.07.2024 4 / 62 p is 2+, +, – or 2–; g is 1 or 2; G is selected from R5-C≡C-(CH2)v-CO2–, R5-C≡C-(CH2)v-C(=O)S–, R5-C≡C-(CH2)v- CS2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is selected from 0, 1, 2, 3 or 4, wherein i is selected from 1, 2 and 3, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; A is selected from NR23+, CO2–, C(=O)S–, CS2–, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; E is selected from NR32, NR33+, CO2H, C(=O)SH, CS2H, CO2–, C(=O)S–, CS2–, wherein, for each occurrence independently, R3is selected from H, linear or branched C1- 6 alkyl; X1and X3are independently selected from H, straight-chain or branched C1-4 alkyl, -OH, - NH2, -NHMe or -NMe2; X2is, for each occurrence independently, selected from H, straight-chain or branched C1-4 alkyl, -OH, -NH2, -NHMe or -NMe2; m is selected from 0, 1 and 2; with the proviso that the overall charge of A and E is not 0 and with the proviso that the salt of formula II is overall neutral in charge. In some embodiments of a salt of formula I or II, G is selected from R5-C≡C-(CH2)v-CO2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is se- lected from 0, 1, 2, 3 or 4, wherein i is selected from 1, 2 and 3, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; A is selected from NR23+and CO2–, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; P26767PC00 19.07.2024 5 / 62 E is selected from NR32, NR33+and CO2H, wherein, for each occurrence independently, R3is selected from H, linear or branched C1-6alkyl. In some embodiments of a salt of formula I or II, A is selected from NH3+, NH2Me+, NHMe2+and CO2–. In some embodiments, the present disclosure is directed towards a salt of formula III wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 al- kyl; v is selected from 0, 1, 2, 3 and 4; m is selected from 0, 1 and 2; X2is, for each occurrence independently, selected from H, straight-chain or branched C1-4alkyl, -OH, -NH2, -NHMe or -NMe2; g is 1 or 2, wherein when g is 1, E is NR32, and when g is 2, E is NR33+; R3is, for each occurrence independently, selected from H and C1-6alkyl; R2is, for each occurrence independently, selected from H and C1-6alkyl. In some embodiments of a salt of formula III, R5is H and X2is H. In some embodiments, the present disclosure is directed towards a salt of formula IV P26767PC00 19.07.2024 6 / 62 wherein g is 1 or 2, wherein when g is 1, E is NH2, and when g is 2, E is NH3+; m is selected from 0, 1 and 2; v is selected from 0, 1, 2, 3 and 4. In some embodiments, the present disclosure is directed towards a salt of formula V wherein i is selected from 1, 2 and 3; m is selected from 0, 1 and 2; X1and X3are independently selected from H, straight-chain or branched C1-4alkyl, -OH, - NH2, -NHMe or -NMe2; X2is, for each occurrence independently, selected from H, straight-chain or branched C1-4alkyl, -OH, -NH2, -NHMe or -NMe2. P26767PC00 19.07.2024 7 / 62 In some embodiments of a salt of formula V, X1, X2and X3are independently, and for each occurrence independently, selected from H, methyl, ethyl, n-propyl, iso-propyl and –OH. In some embodiments of a salt of formula V, X2is H and X3is H. In a second aspect, the disclosure is directed to a cosmetic preparation comprising at least one salt according to any of the embodiments described herein. In some embodiments of the cosmetic preparation, the cosmetic preparation further com- prises at least one cosmetic additive selected from the group consisting of surfactants, oil components, emulsifiers, pearlescent waxes, consistency-enhancing agents, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, UV light protection factors, humectants, biogenic agents, antioxidants, de- odorants, antiperspirants, antidandruff agents, film-forming agents, swelling agents, in- sect repellents, self-tanning agents, tyrosine inhibitors (depigmentation agents), hy- drotropes, solubilizers, preservatives, perfumed oils and dyes, as well as mixtures thereof. In some embodiments of the cosmetic preparation, the cosmetic preparation comprises one salt according to any of the embodiments described herein. In some embodiments, the cosmetic preparation comprises two or more salts, e.g. two salts according to any of the embodiments described herein. For example, in some embodiments the cosmetic prep- aration comprises the following two salts, salt 2 and salt 4: In some embodiments of the cosmetic preparation further comprises a carrier, preferably a carrier selected from water, C(2-6)-alcohols, C(1-10)polyols, as well as oil components. In a third aspect, the disclosure is directed to a salt, a composition or a cosmetic preparation according to any of the embodiments described herein, for use as hair care products. P26767PC00 19.07.2024 8 / 62 In a fourth aspect, the disclosure is directed to the use of salts according to any of the em- bodiments described herein, for the production of cosmetic preparations, preferably hair care products. In a fifth aspect, the disclosure is directed to a method for treatment of keratin materials, such as hair, the method comprising applying to the keratin materials a salt or a cosmetic preparation according any of the embodiments described herein. The salts and cosmetic preparations disclosed herein are suitable for cosmetic use, in par- ticular for the protection of healthy hair or the amelioration of damaged hair. Detailed Description of the Disclosure In the context of the present disclosure, formation of a thiol adduct (more precisely a thiol mono-adduct) refers to a process by which one thiol moiety is linked to a salt of the inven- tion and restoration of disulfide bridges refers to a process by which two thiol moieties are linked together (it is understood that the term “disulfde bridges” refers to two thiol moie- ties being linked using the salts of the invention and not directly linked –S-S-bonds). The thiol moieties may, for example, be part of keratin protein. The process of linking the thiol moieties together may involve reaction of each thiol with an electrophilic moiety in the crosslinking agent. The thiol-reactive agents disclosed herein typically react with one thiol moiety to form a thiol adduct (more precisely a thiol mono-adduct) or with two thiol moi- eties to form a crosslinking unit which links the two thiol moieties together. Unless specified otherwise the following general definitions apply to all salts of the disclo- sure according to the description. The term "salt of the disclosure" as used herein, refers to salts represented by formulae I-V and any of the specific examples disclosed herein. It is understood that “independently of each other” means that when a group is occurring more than one time in any salt, its definition on each occurrence is independent from any other occurrence. P26767PC00 19.07.2024 9 / 62 It is further understood that a dashed line or a solid line without attachment, such as –C1-4alkyl, depicts the site of attachment of a residue (i.e. a partial formula). It is further understood that the abbreviations “C” and “N” are representative for all possible degrees of saturation, which typically do not result in radicals, nitrenes or carbenes, i.e. N includes –NH-, –N= and , . In addition, “C” as an atom in an aromatic or heteroaromatic ring which has a substituent Rxat any suitable position, includes =CH– as well as =CRx–. In addition, “C” as an atom in an aromatic or heteroaromatic ring which does not have substituents Rxat any suitable position, includes =CH- and , as the case may be. It is understood and known to the skilled person that the general rules of valency must be abided by. The terms "C1-14 alkyl", "C1-12 alkyl", "C1-11 alkyl" and "C1-6 alkyl" and "C1-4 alkyl” refer to a fully saturated branched or unbranched hydrocarbon moiety having the indicated number of carbon atoms. Representative examples of C1-14 alkyl include, but are not limited to, me- thyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl, iso-pen- tyl, neopentyl, n-hexyl, iso-hexyl, neohexyl, heptyl, octyl, nonyl, decyl, dodecyl, etc. Rep- resentative examples of C1-6 alkyl include, but are not limited to, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, n- hexyl, iso-hexyl or neohexyl. One or more adjacent or non-adjacent CH2groups of C1-14alkyl, C1-12alkyl, C1-11alkyl, C1-6alkyl and C1-4alkyl may independently be substituted by straight-chain or branched C1-6alkyl, -OH, =O, -NH2, -NHMe, -NMe2. Certain parameters used herein, such as p and q, refer to charges. The charge may, for example, be 2+, +, – or 2–. 2+ refers to two positive charges, i.e. the respective ion is doubly positively charged. Conversely, 2– refers to two negative charges, i.e. the respec- tive ion is doubly negatively charged. A charge typically refers to an ion, which may be an entire chemical moiety or fragment or entity. The charge of an ion refers to the overall charge of that ion, which may be calculated by adding all positive and negative charges P26767PC00 19.07.2024 10 / 62 comprised in the ion. As an example, an ion comprising an ammonium group and two car- boxylate groups would have an overall charge of –. The charge of an ion may be delocal- ized over more than one atom. The charge may also be localized on a small number of atoms, such as one atom. Based on the definitions given throughout the application the skilled person knows which combinations are synthetically feasible and realistic, e.g. typically combinations of groups leading to some heteroatoms directly linked to each other, e.g. –O–O–, are not contem- plated, however synthetically feasible combinations, such as –S–N= in a isothiazole are contemplated. In a first aspect, the disclosure is directed towards a salt of formula I wherein q is + or –; p is 2+, +, – or 2–; g is 1 or 2; G is selected from R5-C≡C-(CH2)v-CO2–, R5-C≡C-(CH2)v-C(=O)S–, R5-C≡C-(CH2)v- CS2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is selected from 0, 1, 2, 3 or 4, wherein i is selected from 1, 2 and 3, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6alkyl; L is straight-chain C2-4alkyl, wherein one or more CH2groups may independently be substituted by straight-chain or branched C1-6alkyl, -OH, =O, -NH2, -NHMe, -NMe2; P26767PC00 19.07.2024 11 / 62 A is selected from NR23+, CO2–, C(=O)S–, CS2–, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6alkyl; E is selected from NR32, NR33+, CO2H, C(=O)SH, CS2H, CO2–, C(=O)S–, CS2–, wherein, for each occurrence independently, R3is selected from H, linear or branched C1- 6 alkyl; with the proviso that the overall charge of A and E is not 0 and with the proviso that the salt of formula I is overall neutral in charge. In some embodiments of a salt of formula I, q is +. In some embodiments of a salt of for- mula I, q is –. In some embodiments of a salt of formula I, p is 2+. In some embodiments of a salt of formula I, p is +. In some embodiments of a salt of formula I, p is 2–. In some embodiments of a salt of formula I, p is –. In some embodiments of a salt of formula I, g is 1. In some embodiments of a salt of for- mula I, g is 2. In some embodiments of a salt of formula I, q is +, p is – and g is 1. In some embodiments of a salt of formula I, q is +, p is 2– and g is 2. In some embodiments of a salt of formula I, q is –, p is + and g is 1. In some embodiments of a salt of formula I, q is –, p is 2+ and g is 2. In some embodiments of a salt of formula I, G is selected from R5-C≡C-(CH2)v-CO2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is selected from 0, 1, 2, 3 or 4, wherein i is selected from 1, 2 and 3, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl. In some embodiments of a salt of formula I, G is selected from H- C≡C-(CH2)v-CO2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is selected from 0, 1, 2, 3 or 4, wherein i is selected from 1, 2 and 3. P26767PC00 19.07.2024 12 / 62 In some embodiments of a salt of formula I, q is + and G is [(H2C=CH-CH2)iNH(4-i)]+, wherein i is selected from 1, 2 and 3. In the embodiments described in this paragraph, preferably, p is – and g is 1. In some embodiments of a salt of formula I, q is – and G is selected from R5-C≡C-(CH2)v- CO2–, R5-C≡C-(CH2)v-C(=O)S–and R5-C≡C-(CH2)v-CS2–, wherein v is selected from 0, 1, 2, 3 or 4, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl. In some embodiments of a salt of formula I, q is – and G is R5-C≡C- (CH2)v-CO2–, wherein v is selected from 0, 1, 2, 3 or 4, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl. In some embodiments of a salt of formula I, q is – and G is H-C≡C-(CH2)v-CO2–, wherein v is selected from 0, 1, 2, 3 or 4. In the embodiments described in this paragraph, preferably, p is 2+ and g is 2. In some embodiments of a salt of formula I, L is a straight-chain C2-4 alkyl, wherein one or more CH2 groups may independently be substituted by straight-chain or branched C1-6 al- kyl, -OH. In some embodiments of a salt of formula I, L is a straight-chain C2-4 alkyl, wherein one or more CH2 groups may independently be substituted by -OH. In some embodiments of a salt of formula I, L is straight-chain C2-3 alkyl, wherein one or more CH2 groups may independently be substituted by straight-chain or branched C1-6 alkyl, -OH. In some em- bodiments of a salt of formula I, L is straight-chain C2-3 alkyl, wherein one or more CH2 groups may independently be substituted by -OH. In some embodiments of a salt of formula I, A is selected from NR23+, CO2–, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl. In some embodiments of a salt of formula I, p is + or 2+ and A is NR23+, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl. In some embod- iments of a salt of formula I, p is – or 2– and A is CO2–, C(=O)S–, CS2–, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl. In some em- bodiments of a salt of formula I, p is – or 2– and A is CO2–. P26767PC00 19.07.2024 13 / 62 In some embodiments of a salt of formula I, E is selected from NR32, NR33+, CO2H, CO2–, wherein, for each occurrence independently, R3is selected from H, linear or branched C1-6alkyl. In some embodiments of a salt of formula I, q is +; p is – or 2–; g is 1 or 2; G is [(H2C=CH-CH2)iNH(4-i)]+, wherein i is selected from 1, 2 and 3; L is straight-chain C2-4 alkyl, wherein one or more CH2 groups may independently be substituted by straight-chain or branched C1-6 alkyl, -OH, =O, -NH2, -NHMe, -NMe2; A is selected from CO2–, C(=O)S–, CS2–; E is selected from NR32, CO2H, C(=O)SH, CS2H, wherein, for each occurrence inde- pendently, R3is selected from H, linear or branched C1-6 alkyl; with the proviso that the overall charge of A and E is not 0 and with the proviso that the salt of formula I is overall neutral in charge. In the embodiment described in the previous sentence, L may optionally be straight-chain C2-3 alkyl, wherein one or more CH2 groups may independently be substituted by straight- chain or branched C1-6 alkyl, -OH. In some embodiments of a salt of formula I, q is –; p is 2+ or +; g is 1 or 2; P26767PC00 19.07.2024 14 / 62 G is selected from R5-C≡C-(CH2)v-CO2–, R5-C≡C-(CH2)v-C(=O)S–, R5-C≡C-(CH2)v- CS2–, wherein v is selected from 0, 1, 2, 3 or 4, wherein R5is, for each occurrence inde- pendently, selected from H, linear or branched C1-6 alkyl; L is straight-chain C2-4 alkyl, wherein one or more CH2 groups may independently be substituted by straight-chain or branched C1-6 alkyl, -OH, =O, -NH2, -NHMe, -NMe2; A is NR23+, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; E is selected from NR32, NR33+, CO2H, C(=O)SH, CS2H, wherein, for each occurrence independently, R3is selected from H, linear or branched C1-6 alkyl; with the proviso that the overall charge of A and E is not 0 and with the proviso that the salt of formula I is overall neutral in charge. In some embodiments, the salt of the invention is of formula II wherein q is + or –; p is 2+, +, – or 2–; g is 1 or 2; G is selected from R5-C≡C-(CH2)v-CO2–, R5-C≡C-(CH2)v-C(=O)S–, R5-C≡C-(CH2)v- CS2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is selected from 0, 1, 2, 3 or 4, wherein i is P26767PC00 19.07.2024 15 / 62 selected from 1, 2 and 3, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6alkyl; A is selected from NR23+, CO2–, C(=O)S–, CS2–, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; E is selected from NR32, NR33+, CO2H, C(=O)SH, CS2H, CO2–, C(=O)S–, CS2–, wherein, for each occurrence independently, R3is selected from H, linear or branched C1- 6 alkyl; X1and X3are independently selected from H, straight-chain or branched C1-4 alkyl, -OH, - NH2, -NHMe or -NMe2; X2is, for each occurrence independently, selected from H, straight-chain or branched C1-4 alkyl, -OH, -NH2, -NHMe or -NMe2; m is selected from 0, 1 and 2; with the proviso that the overall charge of A and E is not 0 and with the proviso that the salt of formula II is overall neutral in charge. In some embodiments of a salt of formula II, q is +. In some embodiments of a salt of formula II, q is –. In some embodiments of a salt of formula II, p is 2+. In some embodiments of a salt of formula II, p is +. In some embodiments of a salt of formula II, p is 2–. In some embodi- ments of a salt of formula II, p is –. In some embodiments of a salt of formula II, g is 1. In some embodiments of a salt of for- mula II, g is 2. In some embodiments of a salt of formula II, q is +, p is – and g is 1. In some embodiments of a salt of formula II, q is +, p is 2– and g is 2. In some embodiments of a salt of formula P26767PC00 19.07.2024 16 / 62 II, q is –, p is + and g is 1. In some embodiments of a salt of formula II, q is –, p is 2+ and g is 2. In some embodiments of a salt of formula II, X1is selected from H, straight-chain or branched C1-4 alkyl, -OH, -NH2, -NHMe or -NMe2. In some embodiments of a salt of for- mula II, X1is selected from H, straight-chain or branched C1-4 alkyl, -OH. In some embodi- ments of a salt of formula II, X1is selected from H, -OH. In some embodiments of a salt of formula II, X2is selected from H, straight-chain or branched C1-4 alkyl, -OH. In some embodiments of a salt of formula II, X2is H. In some embodiments of a salt of formula II, X3is selected from H, straight-chain or branched C1-4 alkyl, -OH. In some embodiments of a salt of formula II, X3is H. In some embodiments of a salt of formula II, X2and X3are H and X1is selected from H, straight-chain or branched C1-4 alkyl, -OH. In some embodiments of a salt of formula II, m is 0. In some embodiments of a salt of formula II, m is 1. In some embodiments of a salt of formula II, m is 2. In some embodi- ments of a salt of formula II, m is 0 or 1. In some embodiments of a salt of formula II, G is selected from R5-C≡C-(CH2)v-CO2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is selected from 0, 1, 2, 3 or 4, wherein i is selected from 1, 2 and 3, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl. In some embodiments of a salt of formula II, G is selected from H- C≡C-(CH2)v-CO2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is selected from 0, 1, 2, 3 or 4, wherein i is selected from 1, 2 and 3. In some embodiments of a salt of formula II, q is + and G is [(H2C=CH-CH2)iNH(4-i)]+, wherein i is selected from 1, 2 and 3. In the embodiments described in this paragraph, preferably, p is – and g is 1. P26767PC00 19.07.2024 17 / 62 In some embodiments of a salt of formula II, q is – and G is selected from R5-C≡C-(CH2)v- CO2–, R5-C≡C-(CH2)v-C(=O)S–and R5-C≡C-(CH2)v-CS2–, wherein v is selected from 0, 1, 2, 3 or 4, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl. In some embodiments of a salt of formula II, q is – and G is R5-C≡C- (CH2)v-CO2–, wherein v is selected from 0, 1, 2, 3 or 4, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl. In some embodiments of a salt of formula II, q is – and G is H-C≡C-(CH2)v-CO2–, wherein v is selected from 0, 1, 2, 3 or 4. In the embodiments described in this paragraph, preferably, p is 2+ and g is 2. In some embodiments of a salt of formula II, A is selected from NR23+, CO2–, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl. In some embodiments of a salt of formula II, p is + or 2+ and A is NR23+, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl. In some embod- iments of a salt of formula II, p is – or 2– and A is CO2–, C(=O)S–, CS2–, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl. In some em- bodiments of a salt of formula II, p is – or 2– and A is CO2–. In some embodiments of a salt of formula II, E is selected from NR32, NR33+, CO2H, CO2–, wherein, for each occurrence independently, R3is selected from H, linear or branched C1-6 alkyl. In some embodiments of a salt of formula II, q is +; p is – or 2–; g is 1 or 2; G is [(H2C=CH-CH2)iNH(4-i)]+, wherein i is selected from 1, 2 and 3; A is selected from CO2–, C(=O)S–, CS2–; P26767PC00 19.07.2024 18 / 62 E is selected from NR32, CO2H, C(=O)SH, CS2H, wherein, for each occurrence inde- pendently, R3is selected from H, linear or branched C1-6alkyl; X1and X3are independently selected from H, straight-chain or branched C1-4 alkyl, -OH, - NH2, -NHMe or -NMe2; X2is, for each occurrence independently, selected from H, straight-chain or branched C1-4 alkyl, -OH, -NH2, -NHMe or -NMe2; m is selected from 0, 1 and 2; with the proviso that the overall charge of A and E is not 0 and with the proviso that the salt of formula II is overall neutral in charge. In the embodiment described in the previous sentence, m may optionally be selected from 0 and 1. In some embodiments of a salt of formula II, q is –; p is 2+ or +; g is 1 or 2; G is selected from R5-C≡C-(CH2)v-CO2–, R5-C≡C-(CH2)v-C(=O)S–, R5-C≡C-(CH2)v- CS2–, wherein v is selected from 0, 1, 2, 3 or 4, wherein R5is, for each occurrence inde- pendently, selected from H, linear or branched C1-6 alkyl; A is NR23+, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; E is selected from NR32, NR33+, CO2H, C(=O)SH, CS2H, wherein, for each occurrence independently, R3is selected from H, linear or branched C1-6 alkyl; P26767PC00 19.07.2024 19 / 62 X1and X3are independently selected from H, straight-chain or branched C1-4alkyl, -OH, - NH2, -NHMe or -NMe2; X2is, for each occurrence independently, selected from H, straight-chain or branched C1-4 alkyl, -OH, -NH2, -NHMe or -NMe2; m is selected from 0, 1 and 2; with the proviso that the overall charge of A and E is not 0 and with the proviso that the salt of formula II is overall neutral in charge. In some embodiments of a salt of formula II, G is selected from R5-C≡C-(CH2)v-CO2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is se- lected from 0, 1, 2, 3 or 4, wherein i is selected from 1, 2 and 3, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; A is selected from NH3+, NH2Me+, NHMe2+and CO2–. E is selected from NR32, NR33+and CO2H, wherein, for each occurrence independently, R3is selected from H, linear or branched C1-6 alkyl. In some embodiments, the salt of the invention is of formula III R5is, for each occurrence independently, selected from H, linear or branched C1-6 al- kyl; v is selected from 0, 1, 2, 3 and 4; m is selected from 0, 1 and 2; P26767PC00 19.07.2024 20 / 62 X2is, for each occurrence independently, selected from H, straight-chain or branched C1-4alkyl, -OH, -NH2, -NHMe or -NMe2; g is 1 or 2, wherein when g is 1, E is NR32, and when g is 2, E is NR33+; R3is, for each occurrence independently, selected from H and C1-6 alkyl; R2is, for each occurrence independently, selected from H and C1-6 alkyl. In some embodiments of a salt of formula III, m is 0. In some embodiments of a salt of formula III, m is 1. In some embodiments of a salt of formula III, m is 2. In some embodiments of a salt of formula III, X2is, for each occurrence independently, selected from H, straight-chain or branched C1-4 alkyl, -OH. In some embodiments of a salt of formula III, R5is H. In some embodiments of a salt of formula III, at least two of the three R2groups are, for each occurrence independently, C1-6 alkyl, and the third of the three R2groups is selected from H and C1-6 alkyl. In some embodiments of a salt of formula III, at least one of the three R3groups is H and the other two R3groups are, for each occurrence independently, selected from H and C1-6 alkyl. In some embodiments of a salt of formula III, R5is H, X2is H, two of the three R2groups are, for each occurrence independently, C1-6 alkyl, and the third of the three R2groups is H. In some embodiments of a salt of formula III, R5is H, X2is H, two of the three R2groups are methyl and the third of the three R2groups is H. In some embodiments of a salt of formula III, R5is H, X2is H, m is 1, two of the three R2groups are, for each occurrence independently, C1-6 alkyl, and the third of the three R2groups is H. In some embodiments of a salt of formula III, R5is H, X2is H, m is 1, two of the three R2groups are methyl and the third of the three R2groups is H. P26767PC00 19.07.2024 21 / 62 In some embodiments of a salt of formula III, R5is H, g is 2, v is selected from 2, 3 and 4, m is 1, X2is H, two of the three R2groups are methyl and the third of the three R2groups is H. In some embodiments of a salt of formula III, R5is H, g is 1, v is 0, m is 1, X2is H, two of the three R2groups are methyl and the third of the three R2groups is H. In some embodiments, the salt of the invention is of formula IV wherein g is 1 or 2, wherein when g is 1, E is NH2, and when g is 2, E is NH3+; m is selected from 0, 1 and 2; v is selected from 0, 1, 2, 3 and 4. In some embodiments of a salt of formula IV, m is 0. In some embodiments of a salt of formula IV, m is 1. In some embodiments of a salt of formula IV, m is 2. In some embodiments of a salt of formula IV, g is 1 and m is 1. In some embodiments of a salt of formula IV, g is 1, m is 1 and v is selected from 2, 3 and 4. In some embodiments of a salt of formula IV, g is 2 and m is 1. In some embodiments of a salt of formula IV, g is 2, m is 1 and v is 0. In some embodiments, the salt of the invention is of formula V P26767PC00 19.07.2024 22 / 62 wherein i is selected from 1, 2 and 3; m is selected from 0, 1 and 2; X1and X3are independently selected from H, straight-chain or branched C1-4 alkyl, -OH, - NH2, -NHMe or -NMe2; X2is, for each occurrence independently, selected from H, straight-chain or branched C1-4 alkyl, -OH, -NH2, -NHMe or -NMe2. In some embodiments of a salt of formula V, X1is selected from H, straight-chain or branched C1-4 alkyl, -OH, -NH2, -NHMe or -NMe2. In some embodiments of a salt of for- mula V, X1is selected from H, straight-chain or branched C1-4 alkyl, -OH. In some embod- iments of a salt of formula V, X1is selected from H and OH. In some embodiments of a salt of formula V, X1is H. In some embodiments of a salt of formula V, X2is selected from H, straight-chain or branched C1-4 alkyl, -OH. In some embodiments of a salt of formula V, X2is H. In some embodiments of a salt of formula V, X3is selected from H, straight-chain or branched C1-4 alkyl, -OH. In some embodiments of a salt of formula V, X3is H. In some embodiments of a salt of formula V, X2and X3are H and X1is selected from H, straight-chain or branched C1-4 alkyl, -OH. In some embodiments of a salt of formula V, X2and X3are H and X1is H. In some embodiments of a salt of formula V, m is 0. In some embodiments of a salt of formula V, m is 1. In some embodiments of a salt of formula V, m is 2. In some embodiments of a salt of formula V, X2and X3are H, m is 0, X1is selected from H and OH. In some embodiments of a salt of formula V, X1, X2and X3are H and m is 0. In some embodiments of a salt of formula V, i is 1, X1, X2and X3are H and m is 0. In some embodiments of a salt of formula V, i is 2, X2and X3are H, m is 0 and X1is selected from P26767PC00 19.07.2024 23 / 62 H and OH. In some embodiments of a salt of formula V, i is 3, X1, X2and X3are H and m is 0. In further specific embodiments, the disclosure is directed to the specific examples dis- closed in Table 1. Table 1 The salts of the disclosure may contain one or more asymmetric centers in the molecule. A salt without designation of the stereochemistry is to be understood to include all the optical isomers (e.g., diastereomers, enantiomers, etc.) in pure or substantially pure form, as well as mixtures thereof (e.g. a racemic mixture, or an enantiomerically enriched mixture). It is well known in the art how to prepare such optically active forms (e.g. by resolution of the racemic form by recrystallization techniques, by synthesis from optically-active starting materials, by chiral synthesis, by chromatographic separation using a chiral stationary phase, and other methods). P26767PC00 19.07.2024 24 / 62 The salts may be isotopically-labeled compounds, for example, compounds including var- ious isotopes of hydrogen, carbon, nitrogen, oxygen. The disclosed salts may exist in tau- tomeric forms and mixtures and separate individual tautomers are contemplated. In addi- tion, some salts may exhibit polymorphism. The salts of the disclosure may exist in solid, i.e. crystalline (e.g., polymorphs, i.e., different crystalline structures that have the same chemical composition but differ in packing, geo- metrical arrangement) or noncrystalline form (optionally as solvates) or liquid form. In the solid state, it may exist in, or as a mixture thereof. In crystalline solvates, solvent molecules are incorporated into the crystalline lattice during crystallization. The formation of solvates may include non-aqueous solvents such as, but not limited to, ethanol, isopropanol, DMSO, acetic acid, ethanolamine, or ethyl acetate, or aqueous solvents such as water (also called “hydrates”). Different polymorphs may be produced, for example, by changing or adjust- ing the reaction conditions or reagents. In a further aspect, the disclosure also provides methods of preparation of the salts of for- mula I-V of the disclosure. In yet another aspect, the disclosure further provides a cosmetic preparation comprising an effective amount of one or more of the salts of the disclosure and one or more pharma- ceutically acceptable carriers and / or excipients (also referred to as diluents). The excipients are acceptable in the sense of being compatible with the other ingredients of the formula- tion and not deleterious to the recipient thereof. The term "effective amount" as used herein refers to the amount of a salt (as such or in form of a cosmetic preparation) of the present disclosure which is effective for producing the desired effect of hair repair. Typically, the pH of the cosmetic preparation is 3.5-6, particularly 4-5 at 20 °C. The pH may, for example, be adjusted using lactic acid, citric acid and the like. Typically, the concentration of the salt disclosed herein will be between 0.01% and 5% by weight of the cosmetic preparation, such as 2%-4% by weight. In some embodiments, P26767PC00 19.07.2024 25 / 62 the concentration of the salt disclosed herein is 50-130 mmol per liter of the cosmetic preparation, particularly 80-100 mmol per liter. In some embodiments, the cosmetic preparation comprises a solubilizer. The concentration of the solubilizer may, for example, be 5%-20% by weight of the cosmetic preparation, particularly 10%-20%, e.g.15%-20%. In some embodiments, the cosmetic preparation comprises phenoxyethanol at a concen- tration of 0.1%-1.7% by weight of the cosmetic preparation, particularly 0.7%-1.1%, e.g. 0.9%. In some embodiments, the cosmetic preparation comprises ethylhexylglycerin at a concen- tration of 0.01%-0.2% by weight of the cosmetic preparation, particularly 0.08%-0.12%, e.g.0.1%. The phrase "pharmaceutically-acceptable carrier" as used herein means a pharmaceuti- cally-acceptable material, composition or vehicle, such as a liquid or solid filler, diluent, excipient, manufacturing aid (e.g., lubricant, talc magnesium, calcium or zinc stearate, or steric acid), or solvent encapsulating material, involved in carrying or transporting the sub- ject salt or compound from one organ, or portion of the body, to another organ, or portion of the body. Each carrier must be "acceptable" in the sense of being compatible with the other ingredients of the formulation and not injurious to the person being treated. Some examples of materials which can serve as pharmaceutically-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 carboxymethyl cellulose, ethyl cel- lulose and cellulose acetate; (4) powdered tragacanth; (5) malt; (6) gelatin; (7) talc; (8) excipients, such as cocoa butter and suppository waxes; (9) oils, such as peanut oil, cot- tonseed oil, safflower oil, sesame oil, olive oil, corn oil and soybean oil; (10) glycols, such as propylene glycol; (11) polyols, such as glycerin, sorbitol, mannitol and polyethylene glycol; (12) esters, such as ethyl oleate and ethyl laurate; (13) agar; (14) buffering agents, such as magnesium hydroxide and aluminum hydroxide; (15) alginic acid; (16) pyrogen- P26767PC00 19.07.2024 26 / 62 free water; (17) isotonic saline; (18) Ringer's solution; (19) ethyl alcohol; (20) pH buff- ered solutions; (21) polyesters, polycarbonates and / or polyanhydrides; and (22) other non-toxic compatible substances employed in cosmetic preparations. Such compositions may contain further components conventional in cosmetic preparations, e.g. wetting agents, emulsifiers and lubricants, such as sodium lauryl sulfate and magne- sium stearate, as well as coloring agents, release agents, coating agents, sweetening, fla- voring and perfuming agents, preservatives and antioxidants, pH modifiers, bulking agents, and further active agents. Examples of pharmaceutically-acceptable antioxidants include: (1) water soluble antioxidants, such as ascorbic acid, cysteine hydrochloride, sodium bi- sulfate, sodium metabisulfite, sodium sulfite and the like; (2) oil-soluble antioxidants, such as ascorbyl palmitate, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), lecithin, propyl gallate, alpha-tocopherol, and the like; and (3) metal chelating agents, such as citric acid, ethylenediamine tetraacetic acid (EDTA), sorbitol, tartaric acid, phos- phoric acid, and the like. Such compositions may be prepared by any method known in the art, for example, by bringing into association the active ingredient with one or more carriers and / or excipients. Different compositions and examples of carriers and / or excipients are well known to the skilled person and are described in detail in, e.g., Remington: The Science and Practice of Pharmacy. Pharmaceutical Press, 2013; Rowe, Sheskey, Quinn: Handbook of Pharmaceu- tical Excipients. Pharmaceutical Press, 2009. Excipients that may be used in the prepara- tion of the cosmetic preparations may include one or more of buffers, stabilizing agents, surfactants, wetting agents, lubricating agents, emulsifiers, suspending agents, preserva- tives, antioxidants, opaquing agents, glidants, processing aids, colorants, sweeteners, per- fuming agents, flavoring agents, diluents and other known additives to provide a compo- sition or preparation suitable for an administration of choice. The cosmetic preparations of the disclosure may be in any suitable form. In some embodi- ments, such suitable forms include but are not limited to liquids, e.g. low to moderate vis- cosity liquids, such as lotions, milks, mousses, sprays, gels, creams, ointments, pastes and P26767PC00 19.07.2024 27 / 62 the like. Suitable excipients, such as those listed above, are included or excluded from the skin formulation depending on the form of use of the formulation (e.g., lotion, gel, oint- ment, or cream). Liquid forms of the salts of the disclosure include pharmaceutically acceptable emulsions, microemulsions, solutions, suspensions, syrups and elixirs. In addition to the active ingre- dient, the liquid forms may contain inert diluents commonly used in the art, such as, for example, water or other solvents, solubilizing agents and emulsifiers, such as ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propyl- ene glycol, 1,3-butylene glycol, oils (in particular, cottonseed, groundnut, corn, germ, ol- ive, castor and sesame oils), glycerol, tetrahydrofuryl alcohol, polyethylene glycols and fatty acid esters of sorbitan, and mixtures thereof. In form of suspensions, a salt may con- tain suspending agents as, for example, ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, benton- ite, agar-agar and tragacanth, and mixtures thereof. In form of sprays, ointments, pastes, creams, lotions, gels, solutions, a salt or compound may be mixed under sterile conditions with a pharmaceutically-acceptable carrier, and with any preservatives, buffers, or propellants which may be required. Such ointments, pastes, creams and gels may contain, in addition to a salt of the disclosure, excipients, such as animal and vegetable fats, oils, waxes, paraffins, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicic acid, talc and zinc oxide, or mixtures thereof. In form of powders and sprays, a salt of the disclosure, may contain excipients such as lactose, talc, silicic acid, aluminum hydroxide, calcium silicates and polyamide powder, or mixtures of these substances. Sprays can additionally contain customary propellants, such as chlorofluorohydrocarbons and volatile unsubstituted hydrocarbons, such as butane and propane. P26767PC00 19.07.2024 28 / 62 In some embodiments, the cosmetic preparations are hair care products, which includes products in form of a shampoo, a conditioner, a hair mask, a hair rinse, hair spray, hair foam, hair mousse, hair gel, hair tonic, and the like. It is understood that all contemplated compositions and preparations must be stable under the conditions of manufacture and storage, and preserved against the contaminating ac- tion of microorganisms, such as bacteria and fungi. The amounts of a salt of the disclosure in the cosmetic preparations of the disclosure may be adjusted in order to obtain an amount of a salt of the disclosure which is effective to achieve the desired cosmetic response for a particular person, composition, and mode of administration, without being deleterious to the person. The chosen amount will depend upon 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 the treatment, other compounds, salts and / or materials used in combination with the particular salt, the age, sex, weight, condition, general health and prior medical history of the person being treated, and like factors well known in the medical arts. Typically, a suitable amount of a salt of the disclosure will be that amount of the salt, which is the lowest amount effective to produce a desired effect. Such an effective dose will gen- erally depend upon the factors described above. In form of shampoo, the amount of cos- metic preparation applied per treatment may, for example, be 1g – 10 g. In form of con- ditioner and / or hair mask, the amount of cosmetic preparation applied per treatment may, for example, be 1 g – 10 g. In form of leave-on conditioner or leave-on mask, the amount of cosmetic preparation applied per treatment may, for example, be 0.1 g – 7 g. All of the salts, compositions, preparations and / or methods disclosed and claimed herein can be made and executed without undue experimentation in light of the present disclo- sure. It will be apparent to those of skill in the art that variations may be applied to the present disclosure without departing from the scope of the disclosure. The Examples pro- vided herein are intended to be illustrative and are not exhaustive; thus, the illustrated Ex- amples should not be viewed as limiting the disclosure in any way. P26767PC00 19.07.2024 29 / 62 Examples Materials: N-Cbz-cysteine was obtained by reduction of its cysteine counterpart via a liter- ature known method. Adv. Syn. Catal., 2020, 362, 5093–5104. Example 1: Synthesis of salt 1 (a) Salt 1 A 250 mL three-neck round flask was charged with acetonitrile (50mL) and propiolic acid (5.0 g) at approximately 10 °C to 20 °C, the batch was charged with nitrogen three times, and then was cooled to approximately -5 °C to 0 °C, and then N1, N1-Dimethyl-propane- 1,3-diamine (7.03 g) was dropped into the mixture. The batch was stirred at approxi- mately -5 °C to 0 °C for 2 hours, and then the mixture was concentrated under vacuum below 20°C to afford 12 g of product as a yellow oil (yield: 100%). 1HNMR (CD3OD): 5.24 (br, s, 4H); 3.25-3.26 (m, 2H); 3.17(s, 2H); 3.06-3.09(m,2H); 2.91(s,6H); 2.11-2.19(m, 2H). (a) Salt 2 A 2.0L reactor was charged with distilled water (500g) and 5-Hexynoic acid (566g) at room temperature, the reaction mixture was cooled to approximately -5 °C to 0 °C. Then the solution of 3-(Dimethylamino)-1-propylamine (510 g) in distilled water (500g) was added to the reactor at approximately -5 °C to 0 °C. The mixture was warmed to approxi- mately 5 °C to 10 °C after addition and stirred at this temperature for 2-3 hours. The solu- tion was the desired compound as yellow solution (2.08Kg, yield: 100%) 1HNMR (MeOD-d4): 2.97(t, 2H); 2.56(t, 2H); 2.36(s, 6H), 2.20-2.30(m, 5H), 1.75- 1.90 (m,4H). P26767PC00 19.07.2024 30 / 62 Example 3: Synthesis of salt 3 (a) Salt 3 A 20L reactor was charged with acetonitrile (5.46kg) and succinic acid (700g) under ni- trogen atmosphere at 20-25 °C. The reaction mixture was warmed to 50-60°C, then Dial- lylamine (610g) was dropped into the reactor within 2 hours, stirred the reaction mixture for 3 hours after addition. Then cooled the temperature to approximately 20 °C to 30°C slowly and stirred at the same temperature range for 8~10 hours. The precipitated solid was collected by filtration, washed the filter cake with acetonitrile (1.09 Kg), and vacuum- dried at approximately 50 °C to 55°C for 10 hours to obtain the target compound as white solid (1.21kg, yield: 95.1%). 1HNMR (DMSO-d6): 7.91-7.44(m, 3H); 5.80-5.90(m, 2H); 5.18-5.30(m, 4H); 3.32(t, 4H); 2.34(s, 4H). (a) Salt 4 A 100 mL three-neck round flask was charged with water (20 mL) and sodium hydroxide (1.69 g) in portions at approximately 10 °C to 20 °C, the mixture was stirred at approxi- mately 10 °C to 20°C for 10min until homogeneous solution was obtained, then succinic acid (5.0 g) was added into it, the resulting mixture was stirred at approximately 10 °C to 20°C for 30min, and then 6.87 g of 35.2% (HPLC assay based on free base) Allylamine hydrochloride aqueous was drooped into the round flask at approximately 10 °C to 20°C, after addition, the mixture was stirred at approximately 10 °C to 20°C for 2 hours to afford 23.56 g of Allylamine succinic acid salt aqueous (yield: 100%). 1HNMR (CD3OD): 5.93-6.03(m, 1H); 5.40-5.50(m, 2H); 3.57-3.59(m,2H); 2.53(s, 4H). P26767PC00 19.07.2024 31 / 62 Example 5: Synthesis of salt 5 (a) Salt 5 A 2.0L reactor R1 was charged with distilled water (750 g) and succinic acid (510 g) at approximately 10 °C to 20 °C, the reaction mixture was cooled to approximately 0 °C to 10 °C and then 430 g of 40.2% sodium hydroxide aq. was dropped into the mixture below 20 °C; the resulting mixture was stirred at approximately 20 °C to 25 °C for 2 hours until a clear solution was obtained as solution A. Another 2.0 L reactor R2 was charged with N, N, N -triallylamine (650 g) at approximately 10 °C to 20°C, the batch in R2 was cooled to approximately 0 °C to 10°C, and then conc. HCl (36.5%, 453 g) was dropped into the mixture below 20°C. The resulting mixture was stirred at approximately 20 °C to 25 °C for 1 hour (labeled as solution B). The solution A was mixed with solution B at approximately 30 °C to 35 °C, and then stirred at this temperature for 1 hour to obtain 2793 g of salt 5 as light red solution (yield 100%);1HNMR (D2O): 5.78-5.89(m, 3H); 5.48-5.53(m, 6H); 3.67(d, 6H); 2.44(s, 4H). Example 6: Thiol modification General procedure The compound to be tested (1 eq.) was dissolved in an aqueous media (0.02 M) and 4 eq. of cysteine reagent (N-Cbz-cysteine) were added. A phosphate buffer (pH=5.4) was used as aqueous medium. To make the phosphate buffer a solution of 0.1-M solution of citric acid (use citric acid monohydrate) and a 0.2-M solution of Na2HPO4 (use Na2HPO4 or Na2HPO4*2H2O) were prepared and mixed with the following ratio: 44.25 mL / 55.75mL = mL 0.1M-citric acid / mL 0.2M Na2HPO4 to give a buffer solution with pH=5.4. The tests were performed at temperatures of 30°C, 40°C or 50°C under stirring with small magnetic stirrers in LC-MS vials or small glass vials. The reactions were performed under normal atmosphere. The reactions were monitored by LC-MS. The reaction scale was be- tween 4 and 10 mg of tested compound. To calculate the conversion into products the ratio between cysteine reagent, the respective mono-adduct (mono) and bis-adduct (bis) were compared. P26767PC00 19.07.2024 32 / 62 Results (a) Conversion at 30°C / 40°C Test compound* Conversion at 30 min Conversion at 60 min 88.86 % mono 87.57 % mono Salt 2 (at 30°C) 0.00 % bis 0.00 % bis 41.03 % mono 47.24 % mono Salt 5 (at 30°C) 0.00 % bis 0.00 % bis 26.99 % mono Salt 4 (at 40°C) - 0.00 % bis * conversion was assessed after dilution of the reaction mixture with MeCN. (b) Conversion at 50°C Test compound* Conversion at 30 min Conversion at 60 min 17.41 % mono 11.99 % mono Salt 2 76.72 % bis 81.54 % bis 96.81 % mono 97.79 % mono Salt 5 0.00 % bis 0.00 % bis 38.55 % mono 73.2 % mono Salt 4 0.00 % bis 0.00 % bis * conversion was assessed after dilution of the reaction mixture with MeCN. Example 7: Compounds tested in examples 8 and 9 In examples 8 and 9, the following compounds were tested using the following names and codes:
[0002] P26767PC00 19.07.2024 33 / 62 Example 8: Tensile Test The in vitro method for investigating the tensile strength of human hair fibers was espe- cially designed to determine hair strengthening or protecting effects of hair care and / or hair cleansing products. In this example, the force needed to pull single hair fibers until 15 % extension, as well as the e-modulus in the resulting force curve were determined as main parameter. The values after application of the test products were compared to baseline values before application. Compounds tested Code / proderm Treatment / Code A Olaplex 0 B ANCV01+ C ANCV02+ P26767PC00 19.07.2024 34 / 62 D ANCV03+ E ANCV04+ The tested compounds are also outlined in example 7. The formulations under investiga- tion are manufactured considering the concentration of the active compound present in Olaplex 0, which is Bis-Aminopropyl Diglycol Dimaleate. The composition of Olaplex 0 comprises water, the active molecule, sodium benzoate, and phenoxyethanol. Methods The study has been conducted in accordance with the study protocol and according to the principles of the quality standard ISO 9001. Description of test procedure: 50 fibers of European natural human hair bleached in a standardized procedure, 2 g of free hair, 21 cm length per treatment code were used. All investigations took place in the air-conditioned room at a temperature of 22 ± 2 °C and at 50 ± 7.5 % relative humidity. Instrumental measurements (baseline, t0): 50 fibers per treatment were prepared by crimping the fibers at a defined hair length. The cross- sectional area of each fiber was measured by laser measurements. Then, the tensile measurements (t0) were performed (see description below). Afterwards, the hair fibers were returned into their initial status by relaxation in deminer- alized water for at least 4 hours. The hair fibers were conditioned overnight under the cli- matic conditions mentioned above. Since some force curves usually show conspicuities e.g. due to the hair slipping from a crimp, the product application was performed on 38 of the 50 fibers after 38 valid curves had been chosen. Afterwards, the product treatment was performed on 38 fibers per product as follows: Product treatment: Codes A to E: ^ Arranging the hair fibers in a special-designed holder ^ Putting the holder into a vessel filled with test product ^ Waiting time of 2 minutes ^ Climatic conditions overnight Instrumental measurements (t1): The cross-sectional area of each fiber was measured by laser measurements. Then, the tensile measurements were repeated. The pH-value of tap water used in this study was about 7 at all times. Instrumental measurement(s): The FDAS675 unit (Dia-Stron, Hampshire, Great Britain) is a laser scanning system for rapid analysis of the cross-sectional data from hair (or other small fibers). Expressing tensile data in terms of force per unit area helps to overcome some P26767PC00 19.07.2024 35 / 62 of the variations given due to differences in the fiber dimensions of the fibers measured. For measuring the cross-sectional area, a hair sample was put into the arms of the FDAS that held the fiber centrally in the laser beam. The fiber was automatically straightened to ensure that the fiber was orthogonal to the laser beam. Since fibers are not cylindrical in cross section, they were rotated in the laser and multiple measurements were made to ob- tain an accurate measure for the cross-sectional area. After measuring the cross-sectional area, the fiber samples, having a testing length of 30 mm, were loaded to the MTT680 (Dia-Stron, Hampshire, Great Britain). Up to 100 single hair fibers can be tested succes- sively in the cassette. The MTT680 locates each successive sample mount and picks it up by a pneumatic jaw which holds the sample during testing. Then, the jaw was moved back- wards and, thus, pulled at the hair fiber until the defined elongation. The force needed to pull the fiber was continuously recorded. On completion of the test, the mount was re- jected and a new sample located. After measuring the tensile strength, the results were automatically normalized by the cross-sectional area. The resulting force curves show a first increase, the so-called elastic phase, then a plateau is reached, the so-called yield phase. Afterwards, the force increases again until the fiber breaks, the so-called post-yield phase. This description is valid for hair fibers. In this study the measurements were stopped after the first phase (in the beginning of the yield phase) to enable recovering of the hair fibers and repetition of tensile measurements on the same hair fiber. ^ Cross-sectional area (FDAS 675, Dia-Stron, Hampshire, Great Britain), mean value of 10 sections. Tensile strength: E-modulus in the first phase [N / m²] and tensile strength at 15 % exten- sion [N / µm²] (MTT 680, Dia-Stron, Hampshire, Great Britain), 1 measurement per assess- ment time. Analysis of data: Raw data of all valid hairs were listed by parameter, treatment and assessment time. Relative differences to baseline were computed as (ti - t0) / t0 * 100 % and listed by treatment and assessment time, where ti was any assessment time after base- line t0. Results Before data analysis, the measuring curves were checked for peculiar curve progression that could occur, for example, if the hair fiber was broken or was pulled out of the crimps holding the hair fiber in place. Values resulting from peculiar curve progression were dis- carded in the following data analysis. Therefore, less than 50 results per product were used. A mean result of at least 25 hair fibers was regarded as valid. A decrease of the parameters e-modulus and tensile strength 15 % is attributed to a posi- tive effect of the treatment on the tensile strength of the investigated hair fibers. Table 2: Descriptive statistics of e-modulus [N / m²] and tensile strength 15 % [N / µm²]. P26767PC00 19.07.2024 36 / 62 e E-modulus Tensile strength 15 % vitCode p s ircitBefore After Relative diff. Before After c s treatment treatment treatment treatment Relative diff. seitat(t0) (t1) [%] (t0) ( [%] D s t1) N 30 30 30 30 30 30 Mean 5.30E+09 4.96E+09 -6.30 1.23E-04 1.17E-04 -4.70 A +SD ± 2.90E+08 ± 2.87E+08 ± 4.91 ± 4.75E-06 ± 3.87E-06 ± 3.70 Median 5.31E+09 4.92E+09 -5.80 1.22E-04 1.17E-04 -3.70 N 33 33 33 33 33 33 Mean 5.15E+09 4.88E+09 -5.19 1.19E-04 1.16E-04 -2.67 B +SD ± 1.99E+08 ± 1.60E+08 ± 3.68 ± 3.64E-06 ± 3.92E-06 ± 1.71 Median 5.16E+09 4.85E+09 -5.60 1.19E-04 1.15E-04 -2.60 N 31 31 31 31 31 31 Mean 5.29E+09 5.06E+09 -4.20 1.24E-04 1.20E-04 -2.91 C +SD ± 2.71E+08 ± 2.39E+08 ± 4.66 ± 3.81E-06 ± 3.82E-06 ± 2.62 Median 5.36E+09 5.05E+09 -3.90 1.24E-04 1.21E-04 -3.20 N 27 27 27 27 27 27 Mean 5.33E+09 5.00E+09 -6.26 1.24E-04 1.19E-04 -4.07 D +SD ± 2.02E+08 ± 2.34E+08 ± 3.91 ± 2.82E-06 ± 3.62E-06 ± 2.87 Median 5.36E+09 4.98E+09 -5.50 1.24E-04 1.19E-04 -4.00 N 27 27 27 27 27 27 Mean 5.73E+09 5.31E+09 -7.11 1.36E-04 1.27E-04 -6.54 E +SD ± 2.88E+08 ± 2.55E+08 ± 5.52 ± 6.89E-06 ± 4.79E-06 ± 4.77 Median 5.66E+09 5.31E+09 -5.50 1.35E-04 1.27E-04 -7.40 Discussion and Conclusion Bleached single hair fibers of hair tresses were stretched in a dry state in the Miniature Tensile Tester until 15 % extension. Afterwards, the hair fibers were relaxed and, subse- quently, treated with the tested products. Then, the tensile strength was determined again. The results of the tensile strength were related to the cross-sectional area of the hair that was previously measured with a laser scanner. The tensile strength is the maximum stress that a material can withstand while being stretched or pulled before breaking. The e-modulus is a measure of an object's resistance to being deformed elastically when a stress is applied to it. The elastic modulus of an ob- ject is defined as the slope of its stress–strain curve in the elastic deformation region: A P26767PC00 19.07.2024 37 / 62 stiffer material has a higher e-modulus value, a more flexible material has lower e-modu- lus values. Considering this behavior in the context of hair damage, a more damaged hair is typically stiffer or more brittle and, therefore, has higher values in e- modulus and ten- sile strength than undamaged hair. For measurements on hair a reduction in the e-modulus and the tensile strength after product treatment therefore indicates an improved hair status. It means that the hair has become smoother and more flexible after the treatment with the test product. Comparisons were performed for the changes of the parameters e-modulus and tensile strength 15 % to benchmark 0 % after the treatment, and between the product-treated fibers. A significant decrease in the parameters e-modulus and tensile strength (15 %) after product application was detected for all tested products when compared to benchmark 0 %, indicating an improved hair status for all treatments. Example 9: Qualitative Tests The salts and compounds examined in this study are detailed in example 7. The in vitro method developed for this example was specifically designed to evaluate the hair-repairing capabilities of preparations intended for use as hair care products on human hair fibers. The studied preparations have similar bond-building technology to Olaplex 0, which re- pairs and strengthens hair. The study aims to demonstrate the effectiveness of the studied preparations in natural virgin hair fibers and to compare the effectiveness of these versus Olaplex 0. In this study, qualitative assessments are performed, including visual and sensorial assess- ment, combing assessment, microscopic evaluation, and bounce evaluation, by using vir- gin human hair strands. These assessments are conducted both on untreated hair samples and on hair samples subjected to common beauty treatments, such as coloring, bleaching, straightening, and keratin treatments. The tested preparations are applied to these pre- treated hair samples with the primary aim of demonstrating their efficacy in repairing hair fibers damaged by these common beauty treatments. The qualitative tests outlined are chosen to assess various parameters related to hair health and appearance. These parameters include overall hair health, softness, texture, shine, vol- ume, frizz, signs of breakage, appearance, manageability, density, moisture retention, ease of combing, combing resistance, breakage resistance, static and frizz, elasticity, uni- formity, integrity, structure of cortex and cuticle, damage, structural uniformity, hair elas- ticity and resilience, stiffness, and strength. P26767PC00 19.07.2024 38 / 62 Materials: Pre-treatments applied to hair samples included coloring treatment (Gar- nier Color Sensation shade S11 Ultra Smoky Blonde Lot: 10Y200), bleaching treatment (Garnier Olia B+++ Blonde Bleach Permanent Hair Dye Lot: 10Y300), straightener (Re- mington Professional Hair Straightener S8593), and keratin treatment (Kativa Keratin Xpress Brazilian Straightening Kit Lot: 230401970; Remington Professional Hair Straight- ener S8593). Hairstyle material used included a comb (a fine-toothed plastic comb is em- ployed to distribute hair treatments and facilitate the alignment of hair strands during styl- ing procedures), an applicator brush (an applicator brush, consisting of synthetic bristles attached to a plastic handle, is employed for the precise and controlled application of hair pre-treatments), a mixing bowl (a plastic mixing bowl is employed for the preparation and blending of hair pre-treatments), and hair elastic (hair elastics, composed of elastic plastic, are employed to separate hair strands). The formulations under investigation are manufactured considering the concentration of the active compound present in Olaplex 0, which is Bis-Aminopropyl Diglycol Dimaleate. The composition of Olaplex 0 comprises water, the active molecule, sodium benzoate, and phenoxyethanol. The preparations have been formulated to match the molar concentration of the active molecule found in the Olaplex 0 product. As a result, these preparations consist of water, the active component (comprising molecules 1–6 and a molecule mix), sodium benzoate, and phenoxyethanol. Table 3: Preparations applied to hair samples Preparation code Description ANCV00 Blank (sodium benzoate and phenoxyethanol) ANCV01 Pro-amino X (molecule 1) ANCV02 Trialyl S (molecule 2) ANCV03 Succonium (molecule 3) ANCV04 Aminalyl S (molecule 4) ANCV07 Pro-amino X + Aminalyl S (molecule mix) Olaplex 0 product Olaplex 0 Lot: 0L0703-20343E Among the treatments applied, ANCV00 (preservatives solution), is the most detrimental treatment to the hair. P26767PC00 19.07.2024 39 / 62 Methods Climatic conditions: All investigations are conducted within a controlled environment in an air-conditioned room maintained at a temperature of 22 ± 2 °C and a relative humidity of 50 ± 7.5%. Table 4: Hair pre-treatments applied to samples Pre-treatment code Description Tr0 Untreated Tr1 Coloring pre-treatment Tr2 Bleaching pre-treatment Tr3 Straightening pre-treatment Tr4 Keratin pre-treatment Among the pre-treatments applied, Tr2 is identified as the most damaging to the hair, followed sequentially by Tr1, Tr0, Tr3, and Tr4. Tr1 - Coloring hair pre-treatment description: The hair samples designated as T1, T1- ANCV00, T1-Olaplex, T1-ANCV01, T1-ANCV02, T1-ANCV03, T1- ANCV04, and T1- ANCV07 are pre-treated using the Garnier Color Sensation shade S11 Ultra Smoky Blonde product. The Garnier Color Sensation product comprises three components: Bottle 1, con- taining developer cream; Bottle 2, containing colorant cream tube; and Bottle 3, contain- ing after-color conditioner. The contents of Bottles 1 and 2 are combined to form the final coloring solution. Hair samples undergo a double combing procedure, following which ap- proximately 10-15 grams of the coloring solution are meticulously applied to each hair sample using an applicator brush. Subsequently, the treated hair is allowed to rest sus- pended in the air for a duration of 35 minutes. Upon completion of the specified time, the product is thoroughly rinsed off with water, and the hair samples are once again hung for drying. The coloring pre-treatment is conducted twice to induce damage to the hair and to observe color alteration in the naturally dark Asian hair. Notably, Bottle 3, containing the after-color conditioner, is not applied to the hair samples during these procedures. Tr2 - Bleaching hair pre-treatment description: The hair samples designated as T2, T2- ANCV00, T2-Olaplex, T2-ANCV01, T2-ANCV02, T2-ANCV03, T2- ANCV04, and T2- ANCV07 are pre-treated using the Garnier Olia B+++ Blonde Bleach Permanent Hair Dye product. The Garnier Olia B+++ product comprises four bottles: Bottle 1, an empty cream applicator bottle; Bottle 2, containing bleaching powder; Bottle 2', containing bleaching cream; and Bottle 3, containing conditioner. The contents of bottles 2 and 2' are combined in bottle 1 to produce the final bleaching solution. Hair samples are combed twice, and approximately 10-15 grams of the bleaching solution are applied to each sample using a P26767PC00 19.07.2024 40 / 62 dye brush. Once applied, the product remains on the hair, exposed to air, for 25 minutes. Subsequently, the product is rinsed off with water, and the hair samples are left to hang until they dry completely. The bleaching pre-treatment is conducted twice to intentionally damage the hair and observe a color change in the dark natural Asian hair. Bottle 3, con- taining conditioner, is not applied to the hair samples. Tr3 - Straightening hair pre-treatment description: The hair samples designated as T3, T3- ANCV00, T3-Olaplex, T3-ANCV01, T3-ANCV02, T3-ANCV03, T3- ANCV04, and T3- ANCV07 are combed twice and then straightened five times using the Remington Profes- sional Hair Straightener S8593 at 220ºC. Tr4 - Keratin hair pre-treatment description: The hair samples designated as T4, T4- ANCV00, T4-Olaplex, T4-ANCV01, T4-ANCV02, T4-ANCV03, T4- ANCV04, and T4- ANCV07 are pre-treated using the Kativa Keratin Xpress Brazilian Straightening Kit prod- uct. The Kativa Keratin Xpress product consists of three bottles: Bottle 1 contains the treat- ment mask, bottle 2 contains shampoo, and bottle 3 contains conditioner. Hair samples undergo two combing sessions, followed by the application of approximately 10–15 grams of treatment mask to each sample using a dye brush. Once applied, the product remains on the hair, exposed to air, for 15 minutes. Subsequently, the product is removed with a comb and the hair is dried by brushing. The hair is then straightened five times using the Remington Professional Hair Straightener S8593 at 220°C. Finally, the product is rinsed off with water, and the hair samples are left to dry once again. Bottles 2 and 3, containing shampoo and conditioner respectively, are not applied to the hair samples. Hair treatment: Following the pre-treatment of the hair samples, they undergo treatment with the preparations ANCV00, ANCV01, ANCV02, ANCV03, ANCV04, ANCV07, and the Olaplex 0 product. Hair treatment description: Hair samples T0-ANCV00, T0-Olaplex, T0-ANCV01, T0- ANCV02, T0-ANCV03, T0-ANCV04, T0-ANCV07, T1-ANCV00, T1-Olaplex, T1- ANCV01, T1-ANCV02, T1-ANCV03, T1-ANCV04, T1-ANCV07, T2-ANCV00, T2- Olaplex, T2-ANCV01, T2-ANCV02, T2-ANCV03, T2- ANCV04, T2-ANCV07, T3- ANCV00, T3-Olaplex, T3-ANCV01, T3-ANCV02, T3- ANCV03, T3-ANCV04, T3- ANCV07, T4-ANCV00, T4-Olaplex, T4-ANCV01, T4-ANCV02, T4-ANCV03, T4- ANCV04, and T4-ANCV07 are treated with preparations ANCV00, ANCV01, ANCV02, ANCV03, ANCV04, ANCV07, and Olaplex 0 product. Each hair sample undergoes two combing sessions, and precisely 1 gram of each prepara- tion is meticulously applied to the corresponding hair sample. Hair samples undergo two combing sessions, and 1 gram of each preparation is applied to the respective hair sample using a dye brush. Once applied, the product is left hanging, in P26767PC00 19.07.2024 41 / 62 contact with the air, for 30 minutes. Subsequently, the product is rinsed off with water, and the hair samples are left to hang until they are completely dry. Hair samples: The hair utilized for this study comprises Asian Remy virgin hair, character- ized by its natural black color, straight texture, and absence of any prior treatment; it is both virgin and naturally occurring. Each hair strand sample measures 1 cm in width and has an approximate weight ranging from 2.5 to 3 grams. Table 5: (Pre-)treatments used for hair samples. Sample code Pre-treatment Treatment T0 No pre-treatment No treatment T0-ANCV00 No pre-treatment Preparation ANCV00 applied. T0-Olaplex No pre-treatment Olaplex 0 product applied T0-ANCV01 No pre-treatment Preparation ANCV01 applied T0-ANCV02 No pre-treatment Preparation ANCV02 applied T0-ANCV03 No pre-treatment Preparation ANCV03 applied T0-ANCV04 No pre-treatment Preparation ANCV04 applied T0-ANCV07 No pre-treatment Preparation ANCV07 applied T1 Coloring pre-treatment No treatment T1-ANCV00 Coloring pre-treatment Preparation ANCV00 applied. T1-Olaplex Coloring pre-treatment Olaplex 0 product applied T1-ANCV01 Coloring pre-treatment Preparation ANCV01 applied T1-ANCV02 Coloring pre-treatment Preparation ANCV02 applied T1-ANCV03 Coloring pre-treatment Preparation ANCV03 applied T1-ANCV04 Coloring pre-treatment Preparation ANCV04 applied T1-ANCV07 Coloring pre-treatment Preparation ANCV07 applied T2 Bleaching pre-treatment No treatment T2-ANCV00 Bleaching pre-treatment Preparation ANCV00 applied. T2-Olaplex Bleaching pre-treatment Olaplex 0 product applied T2-ANCV01 Bleaching pre-treatment Preparation ANCV01 applied T2-ANCV02 Bleaching pre-treatment Preparation ANCV02 applied T2-ANCV03 Bleaching pre-treatment Preparation ANCV03 applied T2-ANCV04 Bleaching pre-treatment Preparation ANCV04 applied T2-ANCV07 Bleaching pre-treatment Preparation ANCV07 applied T3 Straightening pre-treatment No treatment T3-ANCV00 Straightening pre-treatment Preparation ANCV00 applied. T3-Olaplex Straightening pre-treatment Olaplex 0 product applied T3-ANCV01 Straightening pre-treatment Preparation ANCV01 applied T3-ANCV02 Straightening pre-treatment Preparation ANCV02 applied P26767PC00 19.07.2024 42 / 62 T3-ANCV03 Straightening pre-treatment Preparation ANCV03 applied T3-ANCV04 Straightening pre-treatment Preparation ANCV04 applied T3-ANCV07 Straightening pre-treatment Preparation ANCV07 applied T4 Keratin pre-treatment No treatment T4-ANCV00 Keratin pre-treatment Preparation ANCV00 applied. T4-Olaplex Keratin pre-treatment Olaplex 0 product applied T4-ANCV01 Keratin pre-treatment Preparation ANCV01 applied T4-ANCV02 Keratin pre-treatment Preparation ANCV02 applied T4-ANCV03 Keratin pre-treatment Preparation ANCV03 applied T4-ANCV04 Keratin pre-treatment Preparation ANCV04 applied T4-ANCV07 Keratin pre-treatment Preparation ANCV07 applied Test procedure Instrumental measurements (bptt): From a 200-gram strand of Asian Remy virgin natural, black, and straight hair without any treatment, 2.5–3 grams of hair are isolated to create a 1 cm-wide hair strand (designated as sample T0). Sample T0 is designated as blank; thus, no pre-treatment or treatment is administered to this hair sample. Subsequently, instru- mental measurements are conducted on sample T0. Instrumental measurements (apt): From a 200-gram strand of Asian Remy virgin natural, black, and straight hair without any treatment, four 2.5–3-gram strands of hair are ex- tracted, resulting in four 1 cm-wide hair strands (designated as samples T1, T2, T3, T4). Samples T1 through T4 undergo pre-treatment with the most common beauty treatments employed in contemporary practices: coloring treatment (Tr1), bleaching treatment (Tr2), straightening treatment (Tr3), and keratin treatment (Tr4). Subsequently, instrumental measurements are conducted on the samples. Instrumental measurements (at): From a 200-gram strand of Asian Remy virgin natural, black, and straight hair without any treatment, forty- five 2.5-3 gram strands of hair are isolated, resulting in forty-five 1 cm-wide hair strands. These strands are designated as samples T0-ANCV00, T0-Olaplex, T0-ANCV01, T0-ANCV02, T0-ANCV03, T0-ANCV04, T0-ANCV07, T1-ANCV00, T1-Olaplex, T1-ANCV01, T1-ANCV02, T1-ANCV03, T1- ANCV04, T1-ANCV07, T2-ANCV00, T2-Olaplex, T2-ANCV01, T2-ANCV02, T2- ANCV03, T2-ANCV04, T2-ANCV07, T3-ANCV00, T3-Olaplex, T3-ANCV01, T3- ANCV02, T3-ANCV03, T3-ANCV04, T3-ANCV07, T4-ANCV00, T4-Olaplex, T4- ANCV01, T4-ANCV02, T4-ANCV03, T4-ANCV04, and T4-ANCV07. These samples are then treated with the preparations. Subsequently, instrumental measurements are con- ducted on all these samples. P26767PC00 19.07.2024 43 / 62 Visual and sensorial assessment: Parameters including overall hair health, softness, tex- ture, shine, volume, frizz, signs of breakage, appearance, manageability, density, uni- formity, and moisture retention are assessed and evaluated. After all pre-treatments, treat- ments, or non-treatments have been administered to the hair samples, they are positioned on the bouncing machine with serial no BMT25 equipment. The visual appearance of each hair sample is assessed, and a comparative analysis is conducted across all samples. Pa- rameters such as overall hair health, appearance, softness, texture, shine, movement, manageability, elasticity, strength, frizz, volume, density, uniformity, and moisture reten- tion are qualitatively determined using the naked eye. The hair samples are closely exam- ined while suspended to discern disparities in appearance, shine, movement, manageabil- ity, frizz, volume, density, uniformity, moisture retention, and overall hair health. This ob- servation is conducted against the backdrop of a white surface. Furthermore, the softness, texture, movement, manageability, elasticity, strength, volume, density, moisture reten- tion, and overall hair health of the samples are assessed by tactile examination using the naked hand. Combing assessment: Parameters such as ease of combing, resistance to combing, break- age resistance, static and frizz, elasticity, and uniformity are evaluated and measured. Af- ter all pre-treatments, treatments, or non-treatments have been administered to the hair samples, they are positioned on the bouncing machine with serial no BMT25 equipment. Each hair sample undergoes evaluation by combing, and a comparative analysis is con- ducted across all samples. Parameters such as ease of combing, combing resistance, breakage resistance, softness, static and frizz, flexibility and movement, volume, align- ment, and uniformity are qualitatively determined. Hair samples are subjected to three combing sessions while suspended to discern differences in ease of combing, combing re- sistance, breakage resistance, softness, static and frizz, flexibility and movement, volume, alignment, and uniformity. Microscopic evaluation: Parameters such as the integrity and structure of the cortex and cuticle, degree of damage, breakage, and structural uniformity are assessed and analyzed (Equipment: Kern Optics OBL 155 serial no: OME19C0379. Software: Micro- scopeVIS2.0Pro). After all pre-treatments, treatments, or non-treatments have been ap- plied to the hair samples, they are positioned on the bouncing machine with serial no BMT25 equipment. Each hair sample is assessed by observing a hair fiber under the micro- scope. Parameters such as integrity and structure of cortex and medulla, hair diameter, porosity, presence of damage and breakage, residue, shape and curvature, structural uni- formity, physical or chemical damage, elasticity, and flexibility are qualitatively determined. A single hair fiber is carefully positioned on a microscope slide with a drop of water and then placed on the microscope stage. Initially, the fiber is observed using the E Plan 4X / 0.11 objective lens. Subsequently, the image is magnified further using the Plan PHP P26767PC00 19.07.2024 44 / 62 10X / 0.25 objective lens. An image of each hair sample fiber is captured at Plan PHP10X / 0.25 magnification. Bouncing evaluation: Parameters such as hair elasticity, resilience, stiffness, strength, moisture content, and overall hair health are assessed through comparative oscillation analysis conducted between samples. Equipment: Bouncing machine serial no: BMT25). After all pre-treatments, treatments, or non-treatments have been applied to the hair sam- ples, they are positioned on the bouncing machine with serial no BMT25 equipment. This machine, designed and built by the technical team, allows hair strands to swing horizon- tally from side to side. The oscillation speed remains constant for all hair samples. Each hair sample undergoes evaluation based on its movement and bouncing capacity when sub- jected to oscillation. The equipment facilitates comparison between two samples, where the sample exhibiting a higher oscillation point indicates greater overall hair health. Param- eters such as hair elasticity, resilience, stiffness, strength, moisture content, and overall hair health are qualitatively assessed. For visual and sensorial assessments, combing assessment, and microscopic evaluation, each sample is rated on a scale from 0 to 10, with 0 indicating the poorest hair condition and 10 indicating the optimal hair condition. The total score for each sample is calculated by summing the individual parameter scores. This calculation is performed for Tr0, Tr1, Tr2, Tr3, and Tr4. Regarding bouncing evaluation, the most relevant comparisons be- tween two samples have been selected. The sample with a higher oscillation point is con- sidered to have greater elasticity and resilience, stiffness, strength, moisture content, and overall hair health. Results for visual and sensorial assessment The evaluated parameters in visual and sensorial assessment encompass overall hair health, softness, texture, shine, volume, frizz, signs of breakage, appearance, managea- bility, density, uniformity, and moisture retention. Each sample is rated on a scale from 0 to 10, with 0 indicating the poorest hair condition and 10 indicating the optimal hair con- dition. The total score for each sample is subsequently calculated by summing the individ- ual parameter scores. This calculation is performed for Tr0, Tr1, Tr2, Tr3, and Tr4. Of the 12 parameters evaluated, including overall hair health, softness, texture, shine, vol- ume, frizz, signs of breakage, appearance, manageability, density, uniformity, and mois- ture retention, the most representative five parameters are selected: overall hair health, softness, texture, shine, and volume. These parameters are presented alongside the total score of all 12 parameters. Table 6: Descriptive statistics of visual and sensorial assessment for Tr0 P26767PC00 19.07.2024 45 / 62 Parameters Overall hair Soft- Tex- Shin Vol- Total health ness ture e ume score T0 7 7 7 6 7 79 T0-ANCV07 7 7 7 7 7 80 Table 7: Descriptive statistics of visual and sensorial assessment for Tr1 Parameters Overall hair Soft- Tex- Shin Vol- Total health ness ture e ume score T0 7 7 7 6 7 79 T1-ANCV04 6 7 7 6 7 80 Table 8: Descriptive statistics of visual and sensorial assessment for Tr2 Parameters Overall hair Soft- Tex- Shin Vol- Total health ness ture e ume score T0 7 7 7 6 7 79 T2 3 3 3 2 3 36 ed T2-ANCV00 2 2 2 1 2 20 ocleT2-ANCV01 5 5 5 5 5 60 p T2-ANCV02 5 5 6 5 6 62 m aST2-ANCV03 5 6 5 5 5 63 T2-ANCV04 6 5 5 6 6 70 T2-ANCV07 5 5 5 5 5 62 Table 9: Descriptive statistics of visual and sensorial assessment for Tr3 P26767PC00 19.07.2024 46 / 62 Parameters Overall hair Soft- Tex- Shin Vol- Total health ness ture e ume score T0 7 7 7 6 7 79 T3 6 6 6 6 7 79 T3-ANCV04 8 9 8 8 8 90 T3-ANCV07 8 7 7 8 7 87 Table 10: Descriptive statistics of visual and sensorial assessment for Tr4 Parameters Overall Softness Texture Shine Volume Total hair health score T0 7 7 7 6 7 79 T4 7 7 7 7 7 80 ed T4-ANCV00 7 6 6 6 6 72 ocleT4-ANCV01 8 7 7 7 8 93 p T4-ANCV02 8 7 7 7 8 91 m aST4-ANCV03 8 8 8 8 8 94 T4-ANCV04 9 9 9 9 9 106 T4-ANCV07 7 8 7 7 8 91 Within each pre-treatment group, the ANCV00 samples exhibit lower scores compared to T0-T4, indicating that the sample containing only preservatives has a detrimental ef- fect on hair. All studied treatments ANCV01, ANCV02, ANCV03, ANCV04 and ANCV07 have hair repair ability. Results for combing tests The evaluated parameters in combing assessment include ease of combing, combing re- sistance, breakage resistance, static and frizz, elasticity, and uniformity. Each sample is rated on a scale from 0 to 10, with 0 indicating the poorest hair condition and 10 indicat- ing the optimal hair condition. The total score for each sample is then calculated by sum- ming the individual parameter scores. This calculation is performed for Tr0, Tr1, Tr2, Tr3, and Tr4. P26767PC00 19.07.2024 47 / 62 Of the 6 parameters evaluated, including ease of combing, combing resistance, breakage resistance, static and frizz, elasticity, and uniformity, the most representative parameters, ease of combing, combing resistance, and breakage resistance are presented, along with the total score of all 6 parameters. Table 11: Descriptive statistics of combing assessment for Tr0 Parameters Ease of Combing re- Breakage re- Total combing sistance sistance Score T0 7 7 7 41 T0-ANCV07 8 8 8 46 Table 12: Descriptive statistics of combing assessment for Tr1 Parameters Ease of Combing re- Breakage re- Total score combing sistance sistance T0 7 7 7 41 T1 5 5 5 30 ed T1-ANCV00 4 4 4 24 ocelT1-ANCV01 7 6 6 37 p T1-ANCV02 7 6 7 38 m aST1-ANCV03 6 7 6 38 T1-ANCV04 8 7 7 43 T1-ANCV07 6 6 6 37 Table 13: Descriptive statistics of combing assessment for Tr2 Parameters Ease of Combing re- Breakage re- Total combing sistance sistance T0 7 7 7 41 Ted2 4 3 3 18 Toc2-ANCV00 3 2 2 13 T2-ANCV01 6 6 6 35 P26767PC00 19.07.2024 48 / 62 T2-ANCV02 6 6 5 34 T2-ANCV03 5 6 6 34 T2-ANCV04 6 6 6 36 T2-ANCV07 5 5 6 34 Table 14: Descriptive statistics of combing assessment for Tr3 Parameters Ease of Combing re- Breakage re- Total score combing sistance sistance T0 7 7 7 41 T3 6 6 6 35 ed T3-ANCV00 6 5 5 31 ocleT3-ANCV01 7 7 7 42 p T3-ANCV02 7 7 7 42 m aST3-ANCV03 7 7 7 42 T3-ANCV04 8 8 9 48 T3-ANCV07 7 7 7 42 Table 15: Descriptive statistics of combing assessment for Tr4 Parameters Ease of Combing re- Breakage re- Total score combing sistance sistance T0 7 7 7 41 T4 7 7 7 41 ed T4-ANCV00 6 5 5 33 ocleT4-ANCV01 8 7 7 45 p T4-ANCV02 8 7 7 46 m aST4-ANCV03 8 7 7 45 T4-ANCV04 9 8 9 50 T4-ANCV07 7 7 8 45 The samples treated with the studied products (TX-ANCV01-07) exhibit higher total scores than the untreated samples (TX) and the samples treated only with preservatives (TX-ANCV00). All studied treatments ANCV01, ANCV02, ANCV03, ANCV04 and ANCV07 have hair repair ability. P26767PC00 19.07.2024 49 / 62 Results for microscopic evaluation The evaluated parameters in microscopic evaluation include integrity and structure of cor- tex and cuticle, damage, breakage, and structural uniformity. Each sample is rated on a scale from 0 to 10, with 0 indicating the poorest hair condition and 10 indicating the op- timal hair condition. The total score for each sample is then calculated by summing the individual parameter scores. This calculation is performed for Tr0, Tr1, Tr2, Tr3, and Tr4. Table 16: Descriptive statistics of microscopic evaluation for Tr0 Parameters Integrity and struc- Dam- Break- Structural Total ture of cortex and age age uniformity score cuticle T0 7 7 7 8 29 T0-ANCV00 4 4 3 4 15 ed T0-Olaplex 4 4 4 5 17 ocelT0-ANCV01 8 7 6 6 27 p T0-ANCV02 8 7 7 7 29 m aST0-ANCV03 8 7 7 7 29 T0-ANCV04 7 7 7 8 29 T0-ANCV07 8 7 7 8 30 Table 17: Descriptive statistics of microscopic evaluation for Tr1 Parameters Integrity and structure Dam- Break- Structural Total of cortex and cuticle age age uniformity score T0 7 7 7 8 29 T1 4 4 3 3 14 e T1-ANCV00 1 1 1 1 4 docT1-Olaplex 4 4 4 5 17 lep T1-ANCV01 5 5 7 6 23 m a T1-ANCV02 7 7 7 7 28 S T1-ANCV03 8 7 7 7 29 T1-ANCV04 8 7 8 7 30 T1-ANCV07 6 6 6 6 24 Table 18: Descriptive statistics of microscopic evaluation for Tr2 P26767PC00 19.07.2024 50 / 62 Parameters Integrity and Dam- Break- Structural Total score structure of cortex age age uniformity and cuticle T0 7 7 7 8 29 T2 0 0 0 0 0 T2-ANCV00 1 1 0 0 2 T2-Olaplex 6 6 5 5 22 T2-ANCV01 7 7 7 7 28 T2-ANCV02 7 7 7 7 28 T2-ANCV03 7 7 7 7 28 T2-ANCV04 9 8 8 8 33 T2-ANCV07 8 8 9 9 34 Table 19: Descriptive statistics of microscopic evaluation for Tr3 Parameters Integrity and Damage Breakage Structural Total structure of cor- uniformity score tex and cuticle T0 7 7 7 8 29 T3 4 4 4 7 19 e T3-ANCV00 2 2 2 5 11 docT3-Olaplex 5 6 5 5 21 lep T3-ANCV01 8 8 8 8 32 m a T3-ANCV02 8 8 8 9 33 S T3-ANCV03 7 7 8 8 30 T3-ANCV04 7 8 8 8 31 T3-ANCV07 9 9 8 9 35 Table 20: Descriptive statistics of microscopic evaluation for Tr4 Parameters Integrity and Damage Breakage Structural Total structure of cor- uniformity score tex and cuticle T0 7 7 7 8 29 lep ed T4 5 5 5 5 20 m aSocT4-ANCV00 2 2 2 2 8 T4-Olaplex 5 5 6 7 23 P26767PC00 19.07.2024 51 / 62 T4-ANCV01 6 6 7 7 26 T4-ANCV02 6 6 7 7 26 T4-ANCV03 6 6 8 7 27 T4-ANCV04 7 7 8 8 30 T4-ANCV07 7 8 8 8 31 The samples treated with the studied products (TX-ANCV01-07) exhibit higher total scores than the untreated samples (TX) and the samples treated only with preservatives (TX-ANCV00). All studied treatments ANCV01, ANCV02, ANCV03, ANCV04 and ANCV07 have hair repair ability. Results for bouncing evaluation The parameters evaluated in the bouncing assessment include hair elasticity and resili- ence, stiffness, strength, moisture content, and overall hair health. The bouncing test is conducted using a Bouncing Machine (serial no: BMT25) equipped with two sample holders. The highest oscillation point between the two samples is compared visually to determine the relative bouncing capacity and overall hair health. The most relevant comparisons between two samples have been selected. o Comparison TX vs T0: The highest oscillation point is determined between T1-T4 vs T0. o ANCV00 vs T0: The highest oscillation point is determined between TX-ANCV00 vs T0. o ANCV00 vs TX: The highest point of oscillation is determined between TX-ANCV00 vs TX. o TX-Olaplex vs T0, TX, TX-ANCV00: The highest point of oscillation is determined be- tween TX-Olaplex vs T0, TX, TX-ANCV00. o TX-ANCV01-07 vs T0, TX, TX-ANCV00, TX-Olaplex: The highest point of oscillation is determined between TX-ANCV01-07 vs T0, TX, TX-ANCV00, TX-Olaplex. The sample exhibiting a higher oscillation point is indicative of greater elasticity and resili- ence, stiffness, strength, moisture content, and overall hair health. Table 21: Visual comparison of bouncing evaluation for Tr0 Sample pair Sample with higher oscillation point P26767PC00 19.07.2024 52 / 62 T0-ANCV00 vs T0 T0 T0-Olaplex vs T0 T0 T0-Olaplex vs T0-ANCV00 T0-Olaplex T0-ANCV01 vs T0 T0-ANCV01 T0-ANCV01 vs T0-ANCV00 T0-ANCV01 T0-ANCV01 vs T0-Olaplex T0-ANCV01 T0-ANCV02 vs T0 T0-ANCV02 T0-ANCV02 vs T0-ANCV00 T0-ANCV02 T0-ANCV02 vs T0-Olaplex T0-ANCV02 T0-ANCV03 vs T0 T0-ANCV03 T0-ANCV03 vs T0-ANCV00 T0-ANCV03 T0-ANCV03 vs T0-Olaplex T0-ANCV03 T0-ANCV04 vs T0 T0-ANCV04 T0-ANCV04 vs T0-ANCV00 T0-ANCV04 T0-ANCV04 vs T0-Olaplex T0-ANCV04 T0-ANCV07 vs T0 T0-ANCV07 T0-ANCV07 vs T0-ANCV00 T0-ANCV07 T0-ANCV07 vs T0-Olaplex T0-ANCV07 Table 22: Visual comparison of bouncing evaluation for Tr1 Sample pair Sample with higher oscillation point T1 vs T0 T0 T1-ANCV00 vs T0 T0 T1-ANCV00 vs T1 T1-ANCV00 T1-Olaplex vs T0 Similar performance T1-Olaplex vs T1 T1-Olaplex T1-Olaplex vs T1-ANCV00 T1-Olaplex T1-ANCV01 vs T0 T1-ANCV01 T1-ANCV01 vs T1 T1-ANCV01 T1-ANCV01 vs T1-ANCV00 T1-ANCV01 T1-ANCV01 vs T1-Olaplex T1-ANCV01 T1-ANCV02 vs T0 T1-ANCV02 T1-ANCV02 vs T1 T1-ANCV02 T1-ANCV02 vs T1-ANCV00 T1-ANCV02 T1-ANCV02 vs T1-Olaplex T1-ANCV02 T1-ANCV03 vs T0 T1-ANCV03 P26767PC00 19.07.2024 53 / 62 T1-ANCV03 vs T1 T1-ANCV03 T1-ANCV03 vs T1-ANCV00 T1-ANCV03 T1-ANCV03 vs T1-Olaplex T1-ANCV03 T1-ANCV04 vs T0 T1-ANCV04 T1-ANCV04 vs T1 T1-ANCV04 T1-ANCV04 vs T1-ANCV00 T1-ANCV04 T1-ANCV04 vs T1-Olaplex T1-ANCV04 T1-ANCV07 vs T0 T1-ANCV07 T1-ANCV07 vs T1 T1-ANCV07 T1-ANCV07 vs T1-ANCV00 T1-ANCV07 T1-ANCV07 vs T1-Olaplex T1-ANCV07 Table 23: Visual comparison of bouncing evaluation for Tr2 Sample pair Sample with higher oscillation point T2 vs T0 T0 T2-ANCV00 vs T0 T0 T2-ANCV00 vs T2 T2 T2-Olaplex vs T0 T0 T2-Olaplex vs T2 T2-Olaplex T2-Olaplex vs T2-ANCV00 T2-Olaplex T2-ANCV01 vs T0 T0 T2-ANCV01 vs T2 T2-ANCV01 T2-ANCV01 vs T2-ANCV00 T2-ANCV01 T2-ANCV01 vs T2-Olaplex T2-ANCV01 T2-ANCV02 vs T0 T0 T2-ANCV02 vs T2 T2-ANCV02 T2-ANCV02 vs T2-ANCV00 T2-ANCV02 T2-ANCV02 vs T2-Olaplex T2-ANCV02 T2-ANCV03 vs T0 T0 T2-ANCV03 vs T2 T2-ANCV03 T2-ANCV03 vs T2-ANCV00 T2-ANCV03 T2-ANCV03 vs T2-Olaplex T2-ANCV03 T2-ANCV04 vs T0 T0 T2-ANCV04 vs T2 T2-ANCV04 T2-ANCV04 vs T2-ANCV00 T2-ANCV04 T2-ANCV04 vs T2-Olaplex T2-ANCV04 P26767PC00 19.07.2024 54 / 62 T2-ANCV07 vs T0 T0 T2-ANCV07 vs T2 T2-ANCV07 T2-ANCV07 vs T2-ANCV00 T2-ANCV07 T2-ANCV07 vs T2-Olaplex T2-ANCV07 Table 24: Visual comparison of bouncing evaluation for Tr3 Sample pair Sample with higher oscillation point T3 vs T0 T0 T3-ANCV00 vs T0 T0 T3-ANCV00 vs T3 T3 T3-Olaplex vs T0 T0 T3-Olaplex vs T3 T3-Olaplex T3-Olaplex vs T3-ANCV00 T3-Olaplex T3-ANCV01 vs T0 T3-ANCV01 T3-ANCV01 vs T3 T3-ANCV01 T3-ANCV01 vs T3-ANCV00 T3-ANCV01 T3-ANCV01 vs T3-Olaplex T3-ANCV01 T3-ANCV02 vs T0 T3-ANCV02 T3-ANCV02 vs T3 T3-ANCV02 T3-ANCV02 vs T3-ANCV00 T3-ANCV02 T3-ANCV02 vs T3-Olaplex T3-ANCV02 T3-ANCV03 vs T0 T3-ANCV03 T3-ANCV03 vs T3 T3-ANCV03 T3-ANCV03 vs T3-ANCV00 T3-ANCV03 T3-ANCV03 vs T3-Olaplex T3-ANCV03 T3-ANCV04 vs T0 T3-ANCV04 T3-ANCV04 vs T3 T3-ANCV04 T3-ANCV04 vs T3-ANCV00 T3-ANCV04 T3-ANCV04 vs T3-Olaplex T3-ANCV04 T3-ANCV07 vs T0 T3-ANCV07 T3-ANCV07 vs T3 T3-ANCV07 T3-ANCV07 vs T3-ANCV00 T3-ANCV07 T3-ANCV07 vs T3-Olaplex T3-ANCV07 Table 25: Visual comparison of bouncing evaluation for Tr4 P26767PC00 19.07.2024 55 / 62 Sample pair Sample with higher oscillation point T4 vs T0 T0 T4-ANCV00 vs T0 T0 T4-ANCV00 vs T4 T4 T4-Olaplex vs T0 T4-Olaplex T4-Olaplex vs T4 T4-Olaplex T4-Olaplex vs T4-ANCV00 T4-Olaplex T4-ANCV01 vs T0 T4-ANCV01 T4-ANCV01 vs T4 T4-ANCV01 T4-ANCV01 vs T4-ANCV00 T4-ANCV01 T4-ANCV01 vs T4-Olaplex T4-ANCV01 T4-ANCV02 vs T0 T4-ANCV02 T4-ANCV02 vs T4 T4-ANCV02 T4-ANCV02 vs T4-ANCV00 T4-ANCV02 T4-ANCV02 vs T4-Olaplex T4-ANCV02 T4-ANCV03 vs T0 T4-ANCV03 T4-ANCV03 vs T4 T4-ANCV03 T4-ANCV03 vs T4-ANCV00 T4-ANCV03 T4-ANCV03 vs T4-Olaplex T4-ANCV03 T4-ANCV04 vs T0 Same T4-ANCV04 vs T4 T4-ANCV04 T4-ANCV04 vs T4-ANCV00 T4-ANCV04 T4-ANCV04 vs T4-Olaplex Same T4-ANCV07 vs T0 Same T4-ANCV07 vs T4 T4-ANCV07 T4-ANCV07 vs T4-ANCV00 T4-ANCV07 T4-ANCV07 vs T4-Olaplex T4-ANCV07 The comparisons show that all salts of the disclosure studied exhibit a higher oscillation point than the controls.
Claims
P26767PC00 19.07.2024 56 / 62 Claims 1. A salt of formula I wherein q is + or –; p is 2+, +, – or 2–; g is 1 or 2; G is selected from R5-C≡C-(CH2)v-CO2–, R5-C≡C-(CH2)v-C(=O)S–, R5-C≡C-(CH2)v- CS2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is selected from 0, 1, 2, 3 or 4, wherein i is selected from 1, 2 and 3, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; L is straight-chain C2-4 alkyl, wherein one or more CH2 groups may independently be substituted by straight-chain or branched C1-6 alkyl, -OH, =O, -NH2, -NHMe, -NMe2; A is selected from NR23+, CO2–, C(=O)S–, CS2–, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; E is selected from NR32, NR33+, CO2H, C(=O)SH, CS2H, CO2–, C(=O)S–, CS2–, wherein, for each occurrence independently, R3is selected from H, linear or branched C1-6alkyl; with the proviso that the overall charge of A and E is not 0 and with the proviso that the salt of formula I is overall neutral in charge.P26767PC00 19.07.2024 57 / 62 2. A salt according to claim 1, wherein L is a straight-chain C2-3alkyl, wherein one or more CH2groups may independently be substituted by straight-chain or branched C1-4 alkyl, -OH.
3. A salt according to claim 1 having formula IIwherein q is + or –; p is 2+, +, – or 2–; g is 1 or 2; G is selected from R5-C≡C-(CH2)v-CO2–, R5-C≡C-(CH2)v-C(=O)S–, R5-C≡C-(CH2)v- CS2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is selected from 0, 1, 2, 3 or 4, wherein i is selected from 1, 2 and 3, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; A is selected from NR23+, CO2–, C(=O)S–, CS2–, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; E is selected from NR32, NR33+, CO2H, C(=O)SH, CS2H, CO2–, C(=O)S–, CS2–, wherein, for each occurrence independently, R3is selected from H, linear or branched C1- 6 alkyl; X1and X3are independently selected from H, straight-chain or branched C1-4 alkyl, -OH, - NH2, -NHMe or -NMe2;P26767PC00 19.07.2024 58 / 62 X2is, for each occurrence independently, selected from H, straight-chain or branched C1-4alkyl, -OH, -NH2, -NHMe or -NMe2; m is selected from 0, 1 and 2; with the proviso that the overall charge of A and E is not 0 and with the proviso that the salt of formula II is overall neutral in charge.
4. A salt according to any one of the preceding claims, wherein G is selected from R5-C≡C-(CH2)v-CO2–and [(H2C=CH-CH2)iNH(4-i)]+, wherein v is se- lected from 0, 1, 2, 3 or 4, wherein i is selected from 1, 2 and 3, wherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; A is selected from NR23+and CO2–, wherein R2is, for each occurrence independently, selected from H, linear or branched C1-6 alkyl; E is selected from NR32, NR33+and CO2H, wherein, for each occurrence inde- pendently, R3is selected from H, linear or branched C1-6 alkyl.
5. A salt according to any one of the preceding claims, wherein A is selected from NH3+, NH2Me+, NHMe2+and CO2–.
6. A salt according to claim 1 having formula IIIwherein R5is, for each occurrence independently, selected from H, linear or branched C1-6 al- kyl;P26767PC00 19.07.2024 59 / 62 v is selected from 0, 1, 2, 3 and 4; m is selected from 0, 1 and 2; X2is, for each occurrence independently, selected from H, straight-chain or branched C1-4 alkyl, -OH, -NH2, -NHMe or -NMe2; g is 1 or 2, wherein when g is 1, E is NR32, and when g is 2, E is NR33+; R3is, for each occurrence independently, selected from H and C1-6 alkyl; R2is, for each occurrence independently, selected from H and C1-6 alkyl.
7. A salt according to claim 6, wherein R5is H and X2is H.
8. A salt according to claim 1 having formula IVwherein g is 1 or 2, wherein when g is 1, E is NH2, and when g is 2, E is NH3+; m is selected from 0, 1 and 2; v is selected from 0, 1, 2, 3 and 4.
9. A salt according to claim 1 having formula VP26767PC00 19.07.2024 60 / 62wherein i is selected from 1, 2 and 3; m is selected from 0, 1 and 2; X1and X3are independently selected from H, straight-chain or branched C1-4 alkyl, -OH, - NH2, -NHMe or -NMe2; X2is, for each occurrence independently, selected from H, straight-chain or branched C1-4 alkyl, -OH, -NH2, -NHMe or -NMe2.
10. A salt according to claim 9, wherein X1, X2and X3are independently, and for each occurrence independently, selected from H, methyl, ethyl, n-propyl, iso-propyl and -OH.
11. A salt according to any one of the two previous claims, wherein X2is H and X3is H.
12. Cosmetic preparations comprising at least one salt according to any one of the pre- ceding claims.
13. Cosmetic preparations according to claim 12, further comprising at least one cos- metic additive selected from the group consisting of surfactants, oil components, emulsifiers, pearlescent waxes, consistency-enhancing agents, thickeners, superfat- ting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phos- pholipids, UV light protection factors, humectants, biogenic agents, antioxidants, deodorants, antiperspirants, antidandruff agents, film-forming agents, swelling agents, insect repellents, self-tanning agents, tyrosine inhibitors (depigmentationP26767PC00 19.07.2024 61 / 62 agents), hydrotropes, solubilizers, preservatives, perfumed oils and dyes, as well as mixtures thereof.
14. Cosmetic preparations according to any one of claims 12-13 further comprising a carrier, preferably a carrier selected from water, C(2-6)-alcohols, C(1-10)polyols, as well as oil components.
15. Use of salts according to any one of claims 1-11 for the production of cosmetic prep- arations, preferably hair care products.
16. Method for treatment of keratin materials, such as hair, the method comprising ap- plying to the keratin materials a salt according to any one of claims 1-11 or a cos- metic preparation according to any one of claims 12-14.
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