WO2023148138A1 - Composés destinés à être utilisés en tant qu'agents de réparation capillaire ou agents de réparation de tissu - Google Patents

Composés destinés à être utilisés en tant qu'agents de réparation capillaire ou agents de réparation de tissu Download PDF

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Publication number
WO2023148138A1
WO2023148138A1 PCT/EP2023/052239 EP2023052239W WO2023148138A1 WO 2023148138 A1 WO2023148138 A1 WO 2023148138A1 EP 2023052239 W EP2023052239 W EP 2023052239W WO 2023148138 A1 WO2023148138 A1 WO 2023148138A1
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alkyl
hair
composition
compound according
independently
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PCT/EP2023/052239
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English (en)
Inventor
Juan SARRIA
Luciana RODRIGUES
Daniela Veloso Okuta
Natassia PEREZ MARCOS
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Clariant International Ltd
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Publication of WO2023148138A1 publication Critical patent/WO2023148138A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/20—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/45—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/002—Preparations for repairing the hair, e.g. hair cure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/38—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/49—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3719—Polyamides or polyimides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair

Definitions

  • the present invention relates to compounds which are suitable as hair repair agents or fabric repair agents, to compositions and kits comprising such compounds, to the use of such compounds as hair repair agents or fabric repair agents, and to methods for treating hair or fabric.
  • the human hair fiber essentially consists of three different, concentric regions: on the outside is the cuticle; concentrically within the cuticle is the cortex, and the medulla is found at the concentric center, within the cortex.
  • a hair is attached to the dermal layer of the skin by means of the follicles, which is a sheath of cells and connective tissue surrounding the root of a hair.
  • the cuticle is the outermost region of the hair fiber and is found to be very keratinous in nature.
  • Each cuticular cell is found to be rich in the di-amino acid cystine, which plays an important role in maintaining the structure of the hair fibers.
  • Each cuticle cell is covered by a proteinaceous membrane referred to as the epicuticle.
  • the epicuticle forms the outermost region of the cuticular region in the hair fiber and is in turn covered with a lipid layer.18-methyl eicosanoic acid forms the major constituent of this layer and is directly responsible for the hydrophobic nature of the hair. Other free lipids are also commonly present in this region. Keratins are one of the main proteins in the human hair fiber.
  • Two cysteine molecules are linked by a disulfide bond to form cystine. Breakage and changes in the disulfide bonds may lead to changes in the properties of hair. Hair strength in particular is found to be a function of, among other things, the disulfide bonds and the stability of these bonds. While there are many more hydrogen bonds present in hair than disulfide bonds, the hydrogen bonds are weaker and more easily broken. During processes such as perming, bleaching and waving, these disulfide bonds may be cleaved which may lead to a decrease in hair strength. Permanent straightening or waving of hair is one such procedure that can cause a significant change in the physical appearance of hair, but may also cause a lot of changes at a physico-chemical and molecular level.
  • Keratin is softened and molded by altering its physicochemical interactions. In turn, this allows for a new hair shape to be formed.
  • the constituent disulfide bonds of the keratin filaments are continually broken, and restructured in accordance with the desired new shape. This may significantly affect the structural integrity and the cystine content present in the fibers.
  • nucleophilic agents are generally used. Reductive agents, such as mercaptans or sulfites break the disulfide bond selectively, such that they can be recombined in the end. This may prevent the disruption of the entire protein.
  • Mercaptan ammonium thioglycolate is a commonly used agent, which is used to convert the disulfide bonds to sulfhydryl groups to relax the keratin. Following this, these groups are yet again reoxidized to reestablish the disulfide bonds. The majority of the protein may remain intact in the hair following these processes. In the case of alkaline agents possessing a hydroxide moiety, however, the disulfide bonds are cleaved in a less selective manner. These agents usually possess a high pH (greater than 9.0). The hydroxyl ions break the disulfide bonds such that a later rearrangement can take place.
  • disulfide bonds are converted into monosulfide cross-links, one example of this being the lanthonization reaction.
  • This reaction is effective and may result in the desired permanent straightening of hair, but some of the disulfide bonds are converted to lanthionine bonds in the process, which may impair the fiber structure and decreases the tensile strength and the elasticity of the hair.
  • bleaching processes may disrupt the disulfide bonds and damage the integrity of the hair.
  • Hydrogen peroxide is the principal component of the majority of bleaching systems, although peroxide alone is not responsible for the complete oxidation, rather its combination with alkali has the desired oxidative effect.
  • the cystine content in the fibers may become highly oxidized and typically around 15- 20% of the disulfide bonds may be degraded during the normal bleaching process. In cases of severe bleaching, such as that of black to light blonde, the percentage may be as high as 45%.
  • cosmetic hair treatment processes such as hair straightening and hair dying may damage hair
  • the hair care industry has sought approaches to hair repair or at least ways to restore the appearance of hair, so that it looks healthy and undamaged.
  • conditioners may comprise fatty alcohols, cationic compounds such as quaternized ammonium compounds, pH adjusters and silicone polymers to increase shine.
  • conditioners After shampooing, the use of conditioners is often recommended as this may provide protection at the surface of the hair fibers from processes such as bleaching, but this conditioning effect is restricted to the surface level. While some smaller molecules can be capable of reaching the cortex, the larger molecules generally act on a cuticular level.
  • Methods of treating damaged hair are disclosed in EP 3001809 B1. These methods involve treating the hair with formulations comprising a binding agent intended to bind to disrupted disulfide bonds. There is a need for hair compositions and treatments that repair and/or strengthen hair and rebuild stronger bonds in damaged hair, such as hair exposed to reducing agents.
  • the compounds according to Formula (I) of the present invention are particularly useful as hair repair agents and/or hair strengthening agents.
  • the compounds according to Formula (I) of the present invention are particularly useful as fabric repair agents and/or fabric strengthening agents.
  • all percentages are by weight (w/w) of the total composition. Unless stated otherwise, all ratios are weight ratios.
  • wt.% means percentage by weight.
  • references to ‘parts’ e.g. a mixture of 1 part X and 3 parts Y
  • QS” or “QSP” means sufficient quantity for 100% or for 100g.
  • molecular weight or “M.Wt.” or “MW” and grammatical equivalents mean the number average molecular weight.
  • R 1 and R 2 are each independently a Michael acceptor;
  • a 1 and A 2 are each independently selected from NH, N(C 1 -C 2 alkyl), preferably are each independently selected from NH, N(CH 3 );
  • R 3 is selected from H, C 1 -C 2 alkyl, preferably is CH 3 ;
  • R 4 is selected from H, C 1 -C 2 alkyl, preferably
  • a 1 and A 2 in the compounds according to Formula (I) are each independently selected from O, NH, N(C 1 -C 4 alkyl). More preferably, A 1 and A 2 in the compounds according to Formula (I) are each independently selected from NH, N(C 1 - C 2 alkyl). Particularly preferably, A 1 and A 2 in the compounds according to Formula (I) are each independently selected from NH, N(CH 3 ).
  • k is an integer from 0 to 5. More preferably, k is an integer from 1 to 4.
  • k is an integer from 1 to 3.
  • k is 2.
  • R 3 in the compounds according to Formula (I) is selected from H, C 1 -C 4 alkyl, CH 2 CH 2 (OCH 2 CH 2 ) m OH.
  • m is an integer from 1 to 5.
  • R 3 in the compounds according to Formula (I) is selected from H, C 1 -C 2 alkyl.
  • R 3 in the compounds according to Formula (I) is CH 3 .
  • R 4 in the compounds according to Formula (I) is selected from H, C 1 -C 4 alkyl, CH 2 CH 2 (OCH 2 CH 2 )mOH.
  • m is an integer from 1 to 5.
  • R 4 in the compounds according to Formula (I) is selected from H, C 1 -C 2 alkyl.
  • R 4 in the compounds according to Formula (I) is selected from H, CH 3 .
  • R 3 is selected from H, C 1 -C 4 alkyl, CH 2 CH 2 (OCH 2 CH 2 ) m OH;
  • R 4 is selected from H, C 1 -C 4 alkyl, CH 2 CH 2 (OCH 2 CH 2 )mOH.
  • each m is independently an integer from 1 to 5.
  • R 3 is selected from H, C 1 -C 2 alkyl;
  • R 4 is selected from H, C 1 -C 2 alkyl.
  • R 3 is CH 3 ; R 4 is selected from H, CH 3 .
  • L 1 and L 2 in the compounds according to Formula (I) are each independently selected from a single bond, a C 1 -C 4 alkylene group, (OCH 2 CH 2 ) n .
  • n is an integer from 1 to 5. More preferably, L 1 and L 2 in the compounds according to Formula (I) are each independently selected from a single bond, a C 1 -C 4 alkylene group. Even more preferably, L 1 and L 2 in the compounds according to Formula (I) are each independently selected from a single bond, a CH 2 group.
  • X- in the compounds according to Formula (I) is selected from F-, Cl-, Br-, I-, triflate, mesylate, tosylate, methylsulfate, HSO4-, 1 ⁇ 2 SO4 2- , dimethylphosphate, 1 ⁇ 2 methylphosphate, 1/3 phosphate, tetrafluoroborate, methylcarbonate, 1 ⁇ 2 carbonate, and mixtures thereof. More preferably, X- in the compounds according to Formula (I) is selected from Cl-, Br-, I-, methylsulfate, and mixtures thereof. Even more preferably, X- in the compounds according to Formula (I) is selected from Cl-, methylsulfate, and mixtures thereof.
  • R 1 and R 2 in the compounds according to Formula (I) are each independently a Michael acceptor.
  • Michael acceptor is known by a person skilled in the art.
  • the term Michael acceptor preferably refers to any moiety containing an olefin activated by conjugation to an electron withdrawing group such as a carbonyl, a nitro or a sulfonyl group.
  • D 1 is a structural unit having 2 or 3 carbon atoms, with the proviso that 2 of said carbon atoms are linked to each other via a double bond;
  • M + is a cation.
  • D 2 is a structural unit having 2 or 3 carbon atoms, with the proviso that 2 of said carbon atoms are linked to each other via a double bond;
  • M + is a cation.
  • D 1 is a structural unit having 2 or 3 carbon atoms, with the proviso that 2 of said carbon atoms are linked to each other via a double bond;
  • D 2 is a structural unit having 2 or 3 carbon atoms, with the proviso that 2 of said carbon atoms are linked to each other via a double bond;
  • M + in the compounds according to Formula (I) is selected from alkali metal cations, 1 ⁇ 2 alkaline earth metal cations, ammonium cations, and mixtures thereof.
  • M + in the compounds according to Formula (I) is selected from Li + , Na + , K + , 1 ⁇ 2 Mg 2+ , 1 ⁇ 2 Ca 2+ , NH 4 + , monoalkyl ammonium, dialkyl ammonium, trialkyl ammonium, tetraalkyl ammonium, and mixtures thereof. Even more preferably, M + in the compounds according to Formula (I) is selected from Na + , K + , NH 4 + , and mixtures thereof. Particularly preferably, M + in the compounds according to Formula (I) is Na + .
  • a 1 and A 2 are each independently selected from NH, N(C 1 -C 2 alkyl), preferably are each independently selected from NH, N(CH 3 );
  • R 3 is selected from H, C 1 -C 2 alkyl, preferably is CH 3 ;
  • R 4 is selected from H, C 1 -C 2 alkyl, preferably is selected from H, CH 3 ;
  • L 1 and L 2 are
  • a 1 and A 2 are each independently selected from NH, N(C 1 -C 2 alkyl), preferably are each independently selected from NH, N(CH 3 );
  • R 3 is selected from H, C 1 -C 2 alkyl, preferably is CH 3 ;
  • R 4 is selected from H, C 1 -C 2 alkyl, preferably is selected from H, CH 3 ;
  • L 1 and L 2 are
  • the compound according to Formula (I) is a compound according to Formula (Ia) or a compound according to Formula (Ib).
  • Compounds according to Formula (Ib) are particularly preferred.
  • Y in the compounds according to Formula (I) is selected from L 1 -CH 2 -CH 2 -N(R 3 )-CH 2 -CH 2 -L 2 , L 1 -CH 2 -CH 2 -N + (R 3 )(R 4 )-CH 2 -CH 2 -L 2 X-.
  • Y in the compounds according to Formula (I) is L 1 -CH 2 -CH 2 -N(R 3 )-CH 2 -CH 2 -L 2 .
  • Y in the compounds according to Formula (I) is L 1 -CH 2 -CH 2 -N + (R 3 )(R 4 )-CH 2 -CH 2 -L 2 X-.
  • R 1 and R 2 are each independently a Michael acceptor; A 1 and A 2 are each independently selected from O, NH, N(C 1 -C 4 alkyl); Y is selected from L 1 -CH 2 -CH 2 -N(R 3 )-CH 2 -CH 2 -L 2 , L 1 -CH 2 -CH 2 -N + (R 3 )(R 4 )-CH 2 -CH 2 -L 2 X-; R 3 is selected from H, C 1 -C 4 alkyl, CH 2 CH 2 (OCH 2 CH 2 ) m OH; R 4 is selected from H, C 1 -C 4 alkyl, CH 2 CH 2 (OCH 2 CH 2 ) m OH; L 1 and L
  • R 1 and R 2 are each independently a Michael acceptor;
  • a 1 and A 2 are each independently selected from NH, N(C 1 -C 2 alkyl), preferably are each independently selected from NH, N(CH 3 );
  • Y is selected from L 1 -CH 2 -CH 2 -N(R 3 )-CH 2 -CH 2 -L 2 , L 1 -CH 2 -CH 2 -N + (R 3 )(R 4 )-CH 2 -CH 2 -L 2 X-;
  • R 3 is selected from H, C 1 -C 2 alkyl, preferably is CH 3 ;
  • R 4 is selected from H, C 1 -C 2 alkyl, preferably is selected from H, CH 3 ;
  • L 1 and L 2 are each independently selected from a single bond, a C 1 -C 4 alkylene group, preferably are each independently selected from a single bond, a CH 2 group;
  • X- is an anion.
  • R 1 and R 2 are each independently a Michael acceptor; A 1 and A 2 are each independently selected from O, NH, N(C 1 -C 4 alkyl); Y is L 1 -CH 2 -CH 2 -N(R 3 )-CH 2 -CH 2 -L 2 ; R 3 is selected from H, C 1 -C 4 alkyl, CH 2 CH 2 (OCH 2 CH 2 )mOH; L 1 and L 2 are each independently selected from a single bond, a C 1 -C 4 alkylene group, (OCH 2 CH 2 )n; each m is independently an integer from 1 to 5; each n is independently an integer from 1 to 5.
  • R 1 and R 2 are each independently a Michael acceptor;
  • a 1 and A 2 are each independently selected from NH, N(C 1 -C 2 alkyl), preferably are each independently selected from NH, N(CH 3 );
  • Y is L 1 -CH 2 -CH 2 -N(R 3 )-CH 2 -CH 2 -L 2 ;
  • R 3 is selected from H, C 1 -C 2 alkyl, preferably is CH 3 ;
  • L 1 and L 2 are each independently selected from a single bond, a C 1 -C 4 alkylene group, preferably are each independently selected from a single bond, a CH 2 group.
  • a 1 and A 2 are each independently selected from NH, N(C 1 -C 2 alkyl), preferably are each independently selected from NH, N(CH 3 );
  • R 3 is selected from H, C 1 -C 2 alkyl, preferably is CH 3 ;
  • M + is a cation;
  • R 1 and R 2 are each independently a Michael acceptor; A 1 and A 2 are each independently selected from O, NH, N(C 1 -C 4 alkyl); Y is L 1 -CH 2 -CH 2 -N + (R 3 )(R 4 )-CH 2 -CH 2 -L 2 X-; R 3 is selected from H, C 1 -C 4 alkyl, CH 2 CH 2 (OCH 2 CH 2 )mOH; R 4 is selected from H, C 1 -C 4 alkyl, CH 2 CH 2 (OCH 2 CH 2 )mOH; L 1 and L 2 are each independently selected from a single bond, a C 1 -C 4 alkylene group, (OCH 2 CH 2 )n; X- is an anion; each m is independently an integer from 1 to 5; each n is independently an integer from 1 to 5.
  • R 1 and R 2 are each independently a Michael acceptor;
  • a 1 and A 2 are each independently selected from NH, N(C 1 -C 2 alkyl), preferably are each independently selected from NH, N(CH 3 );
  • Y is L 1 -CH 2 -CH 2 -N + (R 3 )(R 4 )-CH 2 -CH 2 -L 2 X-;
  • R 3 is selected from H, C 1 -C 2 alkyl, preferably is CH 3 ;
  • R 4 is selected from H, C 1 -C 2 alkyl, preferably is selected from H, CH 3 ;
  • L 1 and L 2 are each independently selected from a single bond, a C 1 -C 4 alkylene group, preferably are each independently selected from a single bond, a CH 2 group;
  • X- is an anion.
  • a 1 and A 2 are each independently selected from NH, N(C 1 -C 2 alkyl), preferably are each independently selected from NH, N(CH 3 );
  • R 3 is selected from H, C 1 -C 2 alkyl, preferably is CH 3 ;
  • R 4 is selected from H, C 1 -C 2 alkyl, preferably is selected from H, CH 3 ;
  • X- is an anion;
  • M + is a cation;
  • Y in the compounds according to Formula (I) is (C 2 -C 5 alkylene)O(CH 2 CH 2 O) k (C 2 -C 5 alkylene).
  • R 1 and R 2 are each independently a Michael acceptor; A 1 and A 2 are each independently selected from O, NH, N(C 1 -C 4 alkyl); Y is (C 2 -C5 alkylene)O(CH 2 CH 2 O)k(C 2 -C5 alkylene); k is an integer from 0 to 5.
  • R 1 and R 2 are each independently a Michael acceptor;
  • a 1 and A 2 are each independently selected from NH, N(C 1 -C 2 alkyl), preferably are each independently selected from NH, N(CH 3 );
  • Y is (C 2 -C 4 alkylene)O(CH 2 CH 2 O)k(C 2 -C 4 alkylene);
  • k is an integer from 1 to 4.
  • R 1 and R 2 are each independently a Michael acceptor;
  • a 1 and A 2 are each independently selected from NH, N(C 1 -C 2 alkyl), preferably are each independently selected from NH, N(CH 3 );
  • M + is a cation.
  • the present invention also relates to a composition comprising a compound according to Formula (I) of the present invention; and optionally one or more further components.
  • the composition of the present invention comprises (a) from 0.1 to 99.9 wt-% of a compound according to Formula (I) of the present invention; and (b) from 0.1 to 99.9 wt-% of one or more further components.
  • the present invention also relates to a composition comprising (a) from 0.1 to 99.9 wt-% of a compound according to Formula (I) of the present invention; and (b) from 0.1 to 99.9 wt-% of one or more further components.
  • the composition of the present invention comprises (a) from 0.1 to 99.9 wt-%, preferably from 0.2 to 75 wt-%, more preferably from 0.3 to 50 wt-%, more preferably from 0.5 to 20 wt-%, more preferably from 0.5 to 10 wt-%, even more preferably from 0.5 to 5 wt-%, even more preferably from 1 to 5 wt- %, particularly preferably from 1 to 3 wt-% of a compound according to Formula (I) of the present invention; and (b) from 0.1 to 99.9 wt-%, preferably from 25 to 99.8 wt-%, more preferably from 50 to 99.7 wt-%, more preferably from 80 to 99.5 wt-%, more preferably from 90 to 99.5 wt-%, even more preferably from 95 to 99.5 wt-%, even more preferably from 95 to 99 wt-%, particularly preferably from 97 to 99 wt-
  • the composition of the present invention comprises (a) from 20 to 80 wt.-%, preferably from 25 to 75 wt.-%, more preferably from 30 to 70 wt.-%, particularly preferably from 40 to 60 wt.-% of a compound according to Formula (I) of the present invention; and (b) from 20 to 80 wt.-%, preferably from 25 to 75 wt.-%, more preferably from 30 to 70 wt.-%, particularly preferably from 40 to 60 wt.-% of one or more further components.
  • the composition of the present invention comprises (a) from 20 to 80 wt.-%, preferably from 25 to 75 wt.-%, more preferably from 30 to 70 wt.-%, particularly preferably from 40 to 60 wt.-% of a compound according to Formula (I) of the present invention; and (b) from 20 to 80 wt.-%, preferably from 25 to 75 wt.-%, more preferably from 30 to 70 wt.-%, particularly preferably from 40 to 60 wt.-% of solvent.
  • Preferred solvents are alcohols and/or water.
  • a particularly preferred solvent is water.
  • the composition of the present invention is an aqueous solution.
  • the composition of the present invention is a cosmetic composition or a fabric care composition.
  • the composition of the present invention is a cosmetic composition.
  • the composition of the invention is selected from the group consisting of shampoo, body wash, facial cleanser, face mask, bubble bath, intimate wash, bath oil, cleansing milk, micellar water, make-up remover, cleansing wipes, hair mask, perfume, liquid soap, shaving soap, shaving foam, cleansing foam, day cream, anti-ageing cream, body milk, body lotion, body mousse, face serum, eye cream, sunscreen lotion, sun cream, face cream, after-shave lotion, pre-shaving cream, depilatory cream, skin-whitening gel, self-tanning cream, anti-acne gel, mascara, foundation, primer, concealer, blush, bronzer, blemish balm (bb) cream, eyeliner, night cream, eye brow gel, highlighter, lip stain, hand sanitizer, hair oil, nail varnish remover, conditioner, hair styling gel,
  • the composition of the invention is selected from the group consisting of shampoo, cleansing milk, micellar water, cleansing wipes, hair mask, liquid soap, cleansing foam, hair oil, conditioner, hair styling gel, hair styling cream, anti-frizz serum, scalp treatment, hair colorant, split end fluid, soap bar, hair treatment, moisturizer, serum, toner, aqua sorbet, cream gel, styling mousse, dry shampoo, hydro-alcoholic gel, hair spray, and combing cream.
  • the composition of the invention is selected from the group consisting of shampoo, hair conditioner, hair tonic, cream rinse, body wash, bubble bath, bath oil, facial cleanser, cleansing mask, cleansing milk, micellar water, make-up remover, cleansing wipes, perfume, soaps, shaving soaps, shaving foams, cleansing foams, face mask, face cream, hand cream, and body lotion.
  • the composition of the invention is selected from the group consisting of shampoo, hair conditioner, hair tonic, cream rinse, cleansing mask, cleansing milk, micellar water, cleansing wipes, soaps, cleansing foams.
  • the cosmetic composition is a hair care composition or skin care composition.
  • the cosmetic composition is a hair care composition.
  • the cosmetic composition is a skin care composition.
  • the cosmetic composition is a shampoo composition or hair conditioner composition.
  • the cosmetic composition is a shampoo composition.
  • the cosmetic composition is a hair conditioner composition.
  • the cosmetic composition preferably comprises one or more further components (F).
  • the composition of the invention is a shampoo composition.
  • the shampoo composition can be in the form of rinse-off products or ‘dry shampoo’ products, can be opaque or transparent, and can be formulated in a wide variety of product forms, including creams, gels, emulsions, mousses, sprays, solutions, and oils.
  • the shampoo composition is in the form of a rinse-off product.
  • the shampoo composition can be a liquid shampoo composition or a solid shampoo composition.
  • the shampoo composition can, for example, be used on human hair and/or scalp or animal hair, preferably human hair and/or scalp.
  • the composition of the invention is a hair conditioner composition.
  • the hair conditioner composition can be in the form of rinse-off products or leave-on products, can be opaque or transparent, and can be formulated in a wide variety of product forms, including creams, gels, emulsions, mousses, sprays, anhydrous systems, milks, and oils.
  • the hair conditioner composition is in the form of a rinse-off product.
  • the hair conditioner composition can be a liquid hair conditioner composition or a solid hair conditioner composition.
  • the composition of the invention preferably comprises one or more further components (F), which can be in an amount of at least 0.01% by weight, preferably at least 0.05% by weight, more preferably at least 0.1% by weight, even more preferably at least 0.5% by weight of the cosmetic composition.
  • the component (F) is selected from the group consisting of acidity regulators, colorants, conditioning agents, emulsifiers, film formers, fragrances, glossers, humectants, lubricants, moisturizers, pigments, preservatives, skin penetration enhancers, stabilizers, surfactants, thickeners, and viscosity modifiers.
  • the component (F) is selected from the group consisting of acidity regulators, glossers, lubricants, and surfactants.
  • Suitable lubricants are, for example, fatty alcohol components having 6 to 18 carbon atoms.
  • the surfactants may, for example, be selected from non-polymeric, cationic quaternary ammonium compounds, in particular cetrimonium chloride (CTAC).
  • CTAC cetrimonium chloride
  • Suitable classical cationic conditioning agents include cationic quaternary ammonium salts.
  • the component (F) is a cationic quaternary ammonium salt.
  • quaternary ammonium salts examples include benzyl triethyl ammonium chloride, cetyl trimethylammonium chloride (cetrimonium chloride, CTAC), behentrimonium chloride (BTAC) or cetylpyridinium chloride.
  • conditioning agents include Quaternium-98 (Genadvance ® Repair), Polyquaternium- 116 and Butylene Glycol (Genadvance ® Life), Lauryl/Myristyl Polyricinoleate and Glycerin (Genadvance ® Hydra), Stearamidopropyl Dimethylamine (Genamin ® SPA), distearyl dimethyl ammonium chloride (Genamin ® DSAP) or Praepagen ® .
  • cationic components a variety of cationic polymers are suitable, including quaternized cellulose ethers, copolymers of vinylpyrrolidone, acrylic polymers, including homopolymers or copolymers of dimethyldiallylammonium chloride or acrylamide. Also suitable are various types of homo- or copolymers derived from acrylic or methacrylic acid, acrylamide, methylacrylamide, diacetone-acrylamide.
  • the component (F) is a glosser. Typical glossers are silicones. Suitable as silicones are volatile or nonvolatile non-ionic silicone fluids, silicone resins, and silicone semisolids or solids.
  • Volatile silicones are linear or cyclic silicones having a measureable vapor pressure, which is defined as a vapor pressure of at least 2 mm of mercury at 20°C. Also suitable are water insoluble nonvolatile silicone fluids including polyalkyl siloxanes, polyaryl siloxanes, polyalkylaryl siloxanes, polyether siloxane copolymers, amine-functional silicones, or mixtures thereof.
  • the composition of the invention may contain from 0.05 to 5%, preferably 0.5 to 5% by weight of at least one oil component. Typical oils are organic oils, which often are esters.
  • the oil component may comprise glyceryl esters of fatty acids, or triglycerides, coconut oil, almond oil, apricot kernel oil, avocado oil, babassu oil, evening primrose oil, camelina sativa seed oil, grape seed oil, macadamia ternifolia seed oil, corn oil, meadowfoam seed oil, mink oil, olive oil, palm kernel oil, safflower oil, sesame oil, soybean oil, sunflower oil, wheat germ oil, and camellia reticulata seed oil.
  • the composition of the invention may contain esters, ethers or alkanes as emollients.
  • the composition of the invention may contain from 0.05 to 5%, preferably 0.5 to 5% by weight of at least one emulsifier.
  • Preferred emulsifiers are, for example, sorbitan esters.
  • the composition of the invention can contain from 0.1 to 10% by weight, preferably from 0.2 to 5% by weight, more preferably from 0.2 to 3% by weight, also more preferably from 0.5 to 5% by weight of at least one rheology modifying agent, in particular a gelling and thickening agent.
  • cellulosic thickeners for example, hydroxyethylcellulose, hydroxypropylcellulose, and carboxymethylcellulose, guar gum, such as hydroxypropylguar, gums of microbial origin, such as xanthan gum and scleroglucan gum, tara gum, and synthetic thickeners, such as crosslinked homo- or copolymers of acrylic acid and/or of acrylamidopropanesulphonic acid.
  • rheology modifying agents include fatty acid amides such as coconut diethanolamide and monoethanolamide, and oxyethylenated monoethanolamide of carboxylic acid alkyl ether. Rheology modifying agents are also known as structuring materials.
  • Common structuring materials include polymeric materials known as "carbomers", including, for example the cross-linked polyacrylic acid polymers available from Lubrizol Corporation under the trademark Carbopol®.
  • Another class of (meth)acylic acid polymers are alkali-swellable emulsion (ASE) polymers.
  • ASE polymers include, for example, Aculyn® 38 copolymer from Dow.
  • Carbomers and ASE polymers belong to a class of materials known as hydrodynamic thickeners. These hydrodynamic thickeners include acid groups in their polymeric structure that, when deprotonated, form anionic charges that repel each other, causing the polymer chains to expand and entangle.
  • Expansion and chain entanglement can give rise to thickening and suspending effects provided by the deprotonated polymers.
  • the properties of these hydrodynamic thickeners are impacted by their molecular weight, acid group content, degree of cross-linking, and extent of swelling. These thickeners are also known as "space filling” or “volume excluding”, and tend to increase both viscosity and yield point as the concentration thereof is increased.
  • hydrodynamic polymers commonly give rise to compositions that exhibit shear thinning or non-Newtonian behavior.
  • Another class of (meth)acrylic acid based rheology modifiers are hydrophobically modified alkali swellable (HASE) polymers.
  • the HASE polymers include acid groups, the deprotonation of which gives rise to polymer swelling. Additionally, the HASE polymers include hydrophobic side groups, chains or blocks that give rise to associative interactions with each other, as well as with other hydrophobic species present in the compositions in which they are employed, for example, hydrophobic groups of surfactants, fatty acids, other thickening agents, and the like. Association creates hydrophobic regions distributed throughout the polymer chain network. This can also help to enhance the properties of the materials as solubilizing agents. Aculyn® 22 and Aculyn® 28 copolymers from Dow and Aqua SF 1® copolymer from Lubrizol Corporation are among the commonly used HASE materials. U.S.
  • Patent 4,529,773 reports alkali-soluble emulsion polymers activated by neutralization to a pH above 6.5, and subsequently acidified in the presence of a surfactant. These are described as useful thickeners in acidic compositions.
  • the polymers are formed from the copolymerization of a monomer system that includes: (1) methacrylic or acrylic acid, (2) methacrylic or acrylic acid ester of a C 8 -C30 alkyl or, as therein more particularly described, a hydrocarbyl monoether of polyethylene glycol, (3) a C1-C4 alkyl acrylate or methacrylate, and, optionally, (4) a small amount of a polyethylenically unsaturated monomer.
  • the composition of the invention (in particular hair conditioner composition) can also comprise as component (F) a fatty compound.
  • the fatty compound may be included in the cosmetic composition at a level of from 0.1 to 20 % by weight, preferably from 1.0 to 10 % by weight.
  • the fatty compound is selected from the group consisting of fatty alcohols (e.g. cetyl alcohol, stearyl alcohol or cetearyl alcohol), fatty acids, fatty alcohol derivatives, fatty acid derivatives, or mixtures thereof. It is understood that the components disclosed can in some instances fall into more than one classification, e.g., some fatty alcohol derivatives can also be classified as fatty acid derivatives. However, a given classification, is not intended to be a limitation on that particular compound but is done so for convenience of classification and nomenclature.
  • fatty alcohols have 14 to 30 or 16 to 22 carbon atoms. These fatty alcohols are saturated and can be linear or branched.
  • fatty alcohols are cetyl alcohol, stearyl alcohol, behenyl alcohol, and mixtures thereof.
  • Preferred fatty acids have from 10 to 30 or from 12 to 22 carbon atoms. These fatty acids can be saturated and can be linear or branched. Also included herein are salts of these fatty acids. Examples of fatty acids are lauric acid, palmitic acid, stearic acid, behenic acid, sebacic acid, or mixtures thereof.
  • the fatty alcohol derivatives and fatty acid derivatives useful herein include alkyl ethers of fatty alcohols, alkoxylated fatty alcohols, alkyl ethers of alkoxylated fatty alcohols, esters of fatty alcohols, fatty acid esters of compounds having esterifiable hydroxy groups, hydroxy-substituted fatty acids, or mixtures thereof.
  • fatty alcohol derivatives and fatty acid derivatives include methyl stearyl ether, polyoxyethylene ethers of behenyl alcohol, ethyl stearate, cetyl stearate, cetyl palmitate, stearyl stearate, myristyl myristate, polyoxyethylene cetyl ether stearate, polyoxyethylene stearyl ether stearate, polyoxyethylene lauryl ether stearate, ethyleneglycol monostearate, polyoxyethylene monostearate, polyoxyethylene distearate, propyleneglycol monostearate, propyleneglycol distearate, trimethylolpropane distearate, sorbitan stearate, polyglyceryl stearate, glyceryl monostearate, glyceryl distearate, glyceryl tristearate, or mixtures thereof.
  • the composition of the invention may comprise an aqueous carrier.
  • the level and species of the aqueous carrier are selected according to the compatibility with other components and other desired characteristic of the cosmetic composition.
  • the aqueous carrier may, for example, be water or water solutions of lower alkyl alcohols or polyhydric alcohols.
  • the lower alkyl alcohols may, for example, be monohydric alcohols having 1 to 6 carbons, often ethanol and/or isopropanol.
  • the polyhydric alcohols may, for example, be propylene glycol, hexylene glycol, glycerin, and/or propane diol.
  • the aqueous carrier is substantially water. Deionized water is preferably used.
  • the cosmetic composition of the invention can comprise up to 80 %, often even up to 95 % by weight of water.
  • the composition of the invention may comprise sorbitol and/or butylene glycol.
  • the composition of the invention may also include as a further component (F) other components being suitable for rendering the compositions more cosmetically or aesthetically acceptable or to provide them with additional usage benefits.
  • Such other components can generally be used individually at levels of from 0.001 % to 5 % by weight.
  • a wide variety of further components (F) can be formulated into the cosmetic composition of the invention.
  • conditioning agents such as panthenol, panthenyl ethyl ether, proteins, hydrolysed proteins (preferably of vegetable or animal origin, for example hydrolysed collagen or hydrolysed keratin), peptides, amino acids, nutrients; antioxidants, such as vitamin E; emollients, such as PPG-3 myristyl ether, trimethyl pentanol hydroxyethyl ether; hair-fixative polymers, such as amphoteric fixative polymers, cationic fixative polymers, anionic fixative polymers, non-ionic fixative polymers, silicone grafted copolymers; preservatives, such as benzyl alcohol, methyl paraben, propyl paraben, imidazolidinyl urea; pH adjusting agents, such as citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium carbonate; salts, in general, such as potassium acetate or sodium chloride; coloring agents; hair oxidizing
  • salt is present at levels from 0.1 to 1 wt.-% of the total composition to adjust the product viscosity.
  • NaOH is present at levels from 0.1 to 1 wt.-% of the total composition to adjust the pH of the formulation.
  • the composition of the invention may contain as a further component (F) a polysorbate for adjusting rheology, for example, polysorbate-20, polysorbate-21, polysorbate-40, polysorbate-60, or mixtures thereof.
  • the polysorbate can be contained in the composition in amounts up to 5% (e.g.0.1 to 5%) by weight.
  • the composition of the invention can also contain as a further component (F) a polypropylene glycol.
  • Preferred polypropylene glycols are those having a weight average molecular weight of from 200 to 100000 g/mol.
  • the polypropylene glycol may be either water-soluble, water-insoluble, or may have a limited solubility in water, depending upon the degree of polymerization and whether other moieties are attached thereto.
  • the desired solubility of the polypropylene glycol in water will depend in large part upon the form of the composition (e.g., leave-on composition, rinse-off composition).
  • the polypropylene glycol can be included in the composition of the invention at a level of up to 10% by weight.
  • the polypropylene glycol has a solubility in water at 25°C of less than about 1 g/100 g water, more preferably a solubility in water of less than about 0.5 g/100 g water, and even more preferably a solubility in water of less than about 0.1 g/100 g water.
  • the polypropylene glycol can be included in the composition of the invention at a level of up to 10% by weight.
  • Preferred low melting point oils are selected from the group consisting of ester oils such as pentaerythritol ester oils, trimethylol ester oils, citrate ester oils, or glyceryl ester oils; poly [alpha]-olefin oils; and mixtures thereof.
  • ester oils such as pentaerythritol ester oils, trimethylol ester oils, citrate ester oils, or glyceryl ester oils
  • Particularly useful pentaerythritol ester oils and trimethylol ester oils are pentaerythritol tetraisostearate, pentaerythritol tetraoleate, trimethylolpropane triisostearate, trimethylolpropane trioleate, or mixtures thereof.
  • Particularly useful glyceryl esters are triisostearin, triolein or trilinolein.
  • the composition of the invention can also contain, as a further component (F), a cationic polymer.
  • Cationic polymers may be present in the composition of the invention for further enhancing deposition performance.
  • Suitable cationic polymers may be homopolymers which are cationically substituted or may be formed from two or more types of monomers.
  • the weight average (Mw) molecular weight of the polymers will generally be between 100000 and 2 million g/mol.
  • the polymers will have cationic nitrogen containing groups such as quaternary ammonium or protonated amino groups, or a mixture thereof. If the molecular weight of the polymer is too low, then the conditioning effect is poor.
  • the cationic nitrogen-containing group will generally be present as a substituent on a fraction of the total monomer units of the cationic polymer.
  • the ratio of the cationic to non-cationic monomer units is selected to give polymers having a cationic charge density in the required range, which is generally from 0.2 to 3.0 meq/gm.
  • the cationic charge density of the polymer is suitably determined via the Kjeldahl method as described in the US Pharmacopoeia under chemical tests for nitrogen determination.
  • Suitable cationic polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functionalities with water soluble spacer monomers such as (meth)acrylamide, alkyl and dialkyl (meth)acrylamides, alkyl (meth)acrylate, vinyl caprolactone and vinyl pyrrolidine.
  • the alkyl and dialkyl substituted monomers preferably have C1-C7 alkyl groups, more preferably C1-3 alkyl groups.
  • Other suitable spacers include vinyl esters, vinyl alcohol, maleic anhydride, propylene glycol and ethylene glycol.
  • the cationic amines can be primary, secondary or tertiary amines, depending upon the particular species and the pH of the composition.
  • Amine substituted vinyl monomers and amines can be polymerized in the amine form and then converted to ammonium by quaternization.
  • the cationic polymers can comprise mixtures of monomer units derived from amine- and/or quaternary ammonium-substituted monomer and/or compatible spacer monomers.
  • Suitable cationic polymers include, for example cationic diallyl quaternary ammonium-containing polymers including, for example, dimethyldiallylammonium chloride homopolymer and copolymers of acrylamide and dimethyldiallylammonium chloride, referred to in the industry (PCPC) as Polyquaternium 6 and Polyquaternium 7, respectively; mineral acid salts of amino-alkyl esters of homo- and co-polymers of unsaturated carboxylic acids having from 3 to 5 carbon atoms, (as described in US4009256A1 from NAT STARCH CHEM CORP); cationic polyacrylamides (as described in WO95/22311A1 Unilever PLC).
  • PCPC cationic diallyl quaternary ammonium-containing polymers
  • Polyquaternium 6 and Polyquaternium 7 mineral acid salts of amino-alkyl esters of homo- and co-polymers of unsaturated carboxylic acids having from 3 to 5 carbon atoms,
  • cationic polymers that can be used include cationic polysaccharide polymers, such as cationic cellulose derivatives, cationic starch derivatives, and cationic guar gum derivatives.
  • Cationic polysaccharide polymers suitable for use in the composition of the invention include monomers of the formula: A-O-[R-N + (R1)(R2)(R3)X-], wherein: A is an anhydroglucose residual group, such as a starch or cellulose anhydroglucose residual.
  • R is an alkylene, oxyalkylene, polyoxyalkylene, or hydroxyalkylene group, or combination thereof.
  • R1, R2 and R3 independently represent alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, or alkoxyaryl groups, each group containing up to about 18 carbon atoms.
  • the total number of carbon atoms for each cationic moiety i.e., the sum of carbon atoms in R1, R2 and R3 is preferably about 20 or less, and X- is an anionic counterion.
  • Another type of cationic cellulose includes the polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryl dimethyl ammonium-substituted epoxide, referred to in the industry (PCPC) as Polyquaternium 24.
  • Suitable cationic polysaccharide polymers include quaternary nitrogen-containing cellulose ethers (e.g. as described in US3962418 from L’Oréal), and copolymers of etherified cellulose and starch (e.g. as described in US3958581 from L’Oréal).
  • a particularly suitable type of cationic polysaccharide polymer that can be used is a cationic guar gum derivative, such as guar hydroxypropyltrimethylammonium chloride (commercially available from Solvay in their JAGUAR trade named series).
  • Cationic polymer may be present in the composition of the invention at levels of from 0.01 to 5 wt.-%, preferably from 0.05 to 1 wt.-%, more preferably from 0.08 to 0.5 wt.-% by total weight of cationic polymer based on the total weight of the composition.
  • the cationic polymers have a number average molecular weight of at least about 5000 g/mol, typically from 10000 g/mol to 10 million g/mol and are selected from the group consisting of copolymers of vinyl monomers having cationic amine or quaternary ammonium functionalities with water soluble spacer monomers such as acrylamide, methacrylamide, alkyl and dialkyl acrylamides, alkyl and dialkyl methacrylamides, alkyl acrylate, alkyl methacrylate, vinyl caprolactone, and vinyl pyrrolidone.
  • suitable spacer monomers include vinyl esters, vinyl alcohol, maleic anhydride, propylene glycol, and ethylene glycol.
  • Preferred cationic polymers are cationic celluloses, cationic starches, and cationic guar gums.
  • Commercially available cationic guar polymers are e.g. Jaguar® from Solvay.
  • the composition of the invention comprises a surfactant system.
  • the surfactant system comprises a surfactant selected from the group consisting of anionic surfactants, cationic surfactants, non- ionic surfactants, zwitterionic surfactants and/or amphoteric surfactants.
  • the composition of the invention comprises a total amount of surfactant of from 0.01 wt.-% to 70 wt.-%, from 0.1 wt.-% to 40%, from 1 wt.-% to 30%, from 2 wt.-% to 20 wt.-%. In at least one embodiment, the composition of the invention comprises an anionic surfactant.
  • the anionic surfactant is selected from the group consisting of (C10-C20)-alkyl and alkylene carboxylates, alkyl ether carboxylates, fatty alcohol sulfates, fatty alcohol ether sulfates, alkylamide sulfates and sulfonates, fatty acid alkylamide polyglycol ether sulfates, alkanesulfonates and hydroxyalkanesulfonates, olefinsulfonates, acyl esters of isethionates, alpha-sulfo fatty acid esters, alkylbenzenesulfonates, alkylphenol glycol ether sulfonates, sulfosuccinates, sulfosuccinic monoesters and diesters, fatty alcohol ether phosphates, protein/fatty acid condensation products, alkyl monoglyceride sulfates and sulfonates, alkyl alcohol ether
  • the anionic surfactants can be used in the form of their water-soluble or water-dispersible salts, examples being the sodium, potassium, magnesium, ammonium, mono-, di-, and triethanolammonium, and analogous alkylammonium salts.
  • the anionic surfactant is the salt of an anionic surfactant comprising 12 to 14 carbon atoms.
  • the anionic surfactant is selected from the group consisting of sodium lauryl sulfate, sodium laureth sulfate, sodium tridecyl sulfate, sodium trideceth sulfate, sodium myristyl sulfate, sodium myreth sulfate, and mixtures thereof.
  • Typical anionic surfactants for use in the composition of the invention include sodium oleyl succinate, ammonium lauryl sulphosuccinate, sodium lauryl sulphate, sodium lauryl ether sulphate, sodium lauryl ether sulphosuccinate, ammonium lauryl sulphate, ammonium lauryl ether sulphate, sodium dodecyl benzene sulphonate, triethanolamine dodecylbenzene sulphonate, sodium cocoyl isethionate, sodium lauryl isethionate, lauryl ether carboxylic acid and sodium N-lauryl sarcosinate.
  • the level of alkyl ether sulphate is from 0.5 wt.-% to 25 wt.-% of the total composition, more preferably from 3 wt.-% to 18 wt.-%, most preferably from 6 wt.-% to 15 wt.-% of the total composition.
  • the total amount of anionic surfactant in the composition of the invention may range from 0.5 wt.-% to 45 wt.-%, more preferably from 1.5 wt.-% to 20 wt.-%.
  • the composition of the invention may comprise fatty acyl isethionate, if present, preferably at a level of from 1 to 10 wt.-%, more preferably from 2 to 8 wt.-%, most preferably from 2.5 to 7.5 wt.-%.
  • a preferred fatty acyl isethionate product comprises fatty acyl isethionate surfactant at a level of from 40 to 80 wt.-% of the product, as well as free fatty acid and/or fatty acid salt at a level of from 15 to 50 wt.-%.
  • fatty acyl isethionate surfactant at a level of from 40 to 80 wt.-% of the product, as well as free fatty acid and/or fatty acid salt at a level of from 15 to 50 wt.-%.
  • greater than 20 wt.-% and less than 45 wt.-%, more preferably greater than 25 wt.-% and less than 45 wt.-% of the fatty acyl isethionate are of chain length greater than or equal to C16; and greater than 50 wt.-%, preferably greater than 60 wt.-% of the free fatty acid/soap is of chain length C16 to C20.
  • the product may contain isethionate salts, which are present typically at levels less than 5 wt.-%, and traces (less than 2 wt.-%) of other impurities.
  • isethionate salts which are present typically at levels less than 5 wt.-%, and traces (less than 2 wt.-%) of other impurities.
  • a mixture of aliphatic fatty acids is used for the preparation of commercial fatty acyl isethionate surfactants.
  • the resulting fatty acyl isethionate surfactants preferably should have more than 20 wt.-%, preferably more than 25 wt.-%, but no more than 45 wt.-%, preferably 35 wt.-% (on basis of fatty acyl isethionate reaction product) of fatty acyl group with 16 or greater carbon atoms to provide both excellent lather and mildness of the resulting fatty acyl isethionate product.
  • the composition of the invention comprises an acylglycinate surfactant.
  • the acylglycinate surfactant conforms to the formula (Y): wherein R 1a is a linear or branched, saturated alkyl group having 6 to 30, preferably 8 to 22, particularly preferably 8 to 18 carbon atoms or is a linear or branched, mono- or polyunsaturated alkenyl group having 6 to 30, preferably 8 to 22, particularly preferably 12 to 18 carbon atoms, and Q a + is a cation.
  • Qa + is selected from the group consisting of Li+, Na+, K+, Mg++, Ca++, Al+++, NH 4 + , a monoalkylammmonium ion, a dialkylammonium ion, a trialkylammonium ion and a tetraalkylammonium ion, or combinations thereof.
  • the acylglycinate surfactant is selected from sodium cocoylglycinate and potassium cocoylglycinate.
  • the acylglycinate surfactant is selected from those conforming to formula (Y), wherein R is C12 alkyl or C14 alkyl.
  • the acylglycinate surfactant is selected from those conforming to formula (Y), wherein R is C16 alkyl or C 18 alkyl.
  • the composition comprises from 0.01 wt.-% to 30 wt.-%, or from 1 wt.-% to 25 wt.-%, preferably from 5 wt.-% to 20 wt.-%, more preferably from 12 wt.-% to 18 wt.-% anionic surfactant.
  • the composition of the invention comprises a glutamate surfactant corresponding to formula (Z) or a salt thereof: wherein R’ is HOOC-CH2-CH2- or M +- OOC-CH 2 -CH2- wherein M + is a cation; and wherein R is a linear or branched, saturated alkyl group having 6 to 30, preferably 8 to 22, more preferably 8 to 18 carbon atoms or is a linear or branched, mono- or polyunsaturated alkenyl group having 6 to 30, preferably 8 to 22, more preferably 12 to 18 carbon atoms.
  • M + is a metal cation.
  • the glutamate surfactant is selected from those conforming to formula (Z), wherein R is C16 alkyl or C 18 alkyl.
  • the composition of the invention comprises a non-ionic surfactant.
  • Non-ionic surfactants may be present in the range 0 to 5 wt.-%.
  • Non-ionic surfactants that can be included in the composition of the invention include condensation products of aliphatic primary or secondary linear or branched chain alcohols or phenols with alkylene oxides, usually ethylene oxide and generally having from 6 to 30 ethylene oxide groups. Alkyl ethoxylates are particularly preferred.
  • alky ethoxylates having the formula R-(OCH2CH2)nOH, where R is an alkyl chain of C12 to C15, and n is 5 to 9.
  • suitable non-ionic surfactants include mono- or di-alkyl alkanolamides. Examples include coco mono- or di-ethanolamide and coco mono-isopropanolamide.
  • Further non-ionic surfactants which can be included in the composition of the invention are alkyl polyglycosides (APGs). Typically, APG is one which comprises an alkyl group connected (optionally via a bridging group) to a block of one or more glycosyl groups.
  • Preferred APGs are defined by the following formula: RO-(G)n wherein R is a branched or straight chain alkyl group which may be saturated or unsaturated, and G is a saccharide group.
  • R may represent a mean alkyl chain length of from about C5 to about C20.
  • R represents a mean alkyl chain length of from about C9 to about C12.
  • G may be selected from C5 or C6 monosaccharide residues, and is preferably a glucoside.
  • G may be selected from the group comprising glucose, xylose, lactose, fructose, mannose and derivatives thereof.
  • G is glucose.
  • the degree of polymerisation, n may have a value of from about 1 to about 10 or more.
  • Suitable alkyl polyglycosides for use in the invention are commercially available and include for example those materials identified as: Oramix NS10 ex Seppic; Plantaren 1200 and Plantaren 2000 ex Henkel.
  • Other sugar-derived non-ionic surfactants which can be included in the composition of the invention include fatty (e.g. C10-C 18 ) N-alkyl (C1-C6) polyhydroxy fatty acid amides, such as C12-C 18 N-methyl glucamides, as described for example in WO9206154 and US5194639, and N-alkoxy polyhydroxy fatty acid amides.
  • the non-ionic surfactant has an HLB (Hydrophilic Lipophilic Balance) of greater than 12.
  • the non-ionic surfactant is selected from the group consisting of ethoxylated or ethoxylated/propoxylated fatty alcohols with a fatty chain comprising from 12 to 22 carbon atoms, ethoxylated sterols, such as stearyl- or lauryl alcohol (EO-7), PEG-16 soya sterol or PEG-10 soya sterol, polyoxyethylene polyoxypropylene block polymers (poloxamers), and mixtures thereof.
  • HLB Hydrophilic Lipophilic Balance
  • the non-ionic surfactant is selected from the group consisting of ethoxylated fatty alcohols, fatty acids, fatty acid glycerides or alkylphenols, in particular addition products of 2 to 30 mol of ethylene oxide and/or 1 to 5 mol of propylene oxide onto C 8 - to C22-fatty alcohols, onto C12- to C22-fatty acids or onto alkyl phenols having 8 to 15 carbon atoms in the alkyl group, C12- to C22-fatty acid mono- and diesters of addition products of 1 to 30 mol of ethylene oxide onto glycerol, addition products of 5 to 60 mol of ethylene oxide onto castor oil or onto hydrogenated castor oil, fatty acid sugar esters, in particular esters of sucrose and one or two C 8 - to C22-fatty acids, INCI: Sucrose Cocoate, Sucrose Dilaurate, Sucrose Distearate, Sucrose Laurate, Sucrose Myristate, Suc
  • the non-ionic surfactant is selected from the group consisting of fatty alcohol ethoxylates (alkylpolyethylene glycols), alkylphenol polyethylene glycols, alkylmercaptan polyethylene glycols, fatty amine ethoxylates (alkylaminopolyethylene glycols), fatty acid ethoxylates (acylpolyethylene glycols), polypropylene glycol ethoxylates (Pluronics®), fatty acid alkylol amides, (fatty acid amide polyethylene glycols), N-alkyl-, N-alkoxypoly-hydroxy-fatty acid amide, sucrose esters, sorbitol esters, polyglycol ethers, and mixtures thereof.
  • fatty alcohol ethoxylates alkylpolyethylene glycols
  • alkylphenol polyethylene glycols alkylmercaptan polyethylene glycols
  • fatty amine ethoxylates alkylaminopoly
  • the composition of the invention comprises a fatty N- methyl-N-glucamide surfactant.
  • the fatty N-methyl-N- glucamide surfactant conforms to the formula (X): wherein R is a linear or branched alkyl or alkenyl group having from 3 to 30 carbon atoms.
  • R is an alkyl group having from 3 to 30 carbon atoms.
  • R is a saturated aliphatic hydrocarbon group which can be linear or branched and can have from 3 to 20 carbon atoms in the hydrocarbon chain, preferably linear or branched.
  • R is selected from the group consisting of 1-propyl, 2-propyl, 1 butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2- pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2 methyl-2-butyl, 3-methyl-2- butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1- pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3 methyl-2-pentyl, 4-methyl-2-pentyl, 2 methyl-3-pentyl, 3-methyl-3-pentyl, 3-methyl-3-pent
  • Suitable fatty N methyl-N-glucamide surfactants are described in WO2013/178700 and EP 0550637, which are incorporated herein by reference.
  • the N-methyl-N-glucamide surfactant is selected from those conforming to formula (X), wherein R is C12 alkyl or C14 alkyl.
  • the N-methyl-N-glucamide surfactant is selected from those conforming to formula (X), wherein R is C16 alkyl or C 18 alkyl.
  • the composition of the invention comprises from 1 wt.-% to 20 wt.-%, more preferably from 2 wt.-% to 10 wt.-%, even more preferably from 3 wt.-% to 7 wt.-% non-ionic surfactant.
  • Amphoteric or zwitterionic surfactant can be included in the composition of the invention in an amount ranging from 0.5 wt.-% to about 8 wt.-%, preferably from 1 wt.-% to 4 wt.-% of the total composition.
  • the amphoteric surfactants are selected from the group consisting of N-(C12-C 18 )-alkyl-beta-aminopropionates and N-(C12-C 18 )-alkyl-beta- iminodipropionates as alkali metal salts and mono-, di-, and trialkylammonium salts; N-acylaminoalkyl-N,N-dimethylacetobetaine, preferably N-(C 8 -C 18 )-acylaminopropyl- N,N-dimethylacetobetaine; (C12-C 18 )-alkyl-dimethyl-sulfopropylbetaine; amphosurfactants based on imidazoline (trade name: Miranol®, Steinapon®), preferably the sodium salt of 1-(beta-carboxymethyloxyethyl)-1-(carboxymethyl)-2- laurylimidazolinium; amine oxide
  • the composition of the invention comprises a betaine surfactant.
  • the betaine surfactant is selected from C 8 - to C 18 - alkylbetaines.
  • the betaine surfactant is selected from the group consisting of cocodimethylcarboxymethylbetaine, lauryldimethylcarboxymethylbetaine, lauryldimethylalphacarboxyethylbetaine, cetyldimethylcarboxymethylbetaine, oleyldimethylgammacarboxypropylbetaine and laurylbis(2-hydroxypropyl)alphacarboxyethylbetaine and combinations thereof.
  • the betaine surfactant is selected from C 8 - to C 18 -sulfobetaines.
  • the betaine surfactant is selected from the group consisting of cocodimethylsulfopropylbetaine, stearyldimethylsulfopropylbetaine, lauryldimethylsulfoethylbetaine, laurylbis(2-hydroxyethyl)sulfopropylbetaine, and combinations thereof.
  • the betaine surfactant is selected from carboxyl derivatives of imidazole, theC 8 - to C 18 -alkyldimethylammonium acetates, the C 8 - to C 18 alkyldimethylcarbonylmethylammonium salts, and the C 8 - to C 18 -fatty acid alkylamidobetaines, and mixtures thereof.
  • the C 8 - to C 18 -fatty acid alkylamidobetaine is selected from coconut fatty acid amidopropylbetaine, N-coconut fatty acid amidoethyl-N-[2-(carboxymethoxy)ethyl]glycerol (PCPC name: cocoamphocarboxyglycinate), and mixtures thereof.
  • a particularly preferred amphoteric or zwitterionic surfactant is cocamidopropyl betaine. Mixtures of any of the foregoing amphoteric or zwitterionic surfactants may also be suitable. Preferred mixtures are those of cocamidopropyl betaine with further amphoteric or zwitterionic surfactants as described above. A preferred further amphoteric or zwitterionic surfactant is sodium cocoamphoacetate.
  • the composition of the invention comprises from 0.5 wt.- % to 20 wt.-%, preferably from 1 wt.-% to 10 wt.-% amphoteric surfactant. In at least one embodiment, the composition of the invention comprises a surfactant system.
  • the surfactant system comprises at least one surfactant selected from the group consisting of lauryl sulfate, laureth sulfate, cocamidopropyl betaine, sodium cocoylglutamate, lauroamphoacetate, and mixtures thereof.
  • the surfactant system comprises sodium laureth sulfate, sodium lauryl sulfate, and optionally cocamidopropyl betaine.
  • the surfactant system comprises sodium laureth sulfate, potassium cocoylglutamate, and cocamidopropyl betaine.
  • the composition of the invention contains as a further component a silicone compound.
  • the composition can comprise up to 5% (e.g.0.1 to 5%) by weight of a silicone compound.
  • Suitable silicone compounds include polyalkyl or polyaryl siloxanes.
  • the preferred silicone compounds are polydimethylsiloxane, polydiethylsiloxane, and polymethylphenylsiloxane, e.g. available from Wacker (Germany) or Dow Corning, such as Xiameter PMX DC 200. Silicone compounds can be available as silicone oils or emulsions.
  • the silicone compounds may further be incorporated in the present composition in the form of an emulsion, wherein the emulsion is pre-made and added to the formulation, or made during the formulation process by mechanical mixing with or without the aid of an additional surfactant selected from anionic surfactants, non-ionic surfactants, cationic surfactants, and mixtures thereof.
  • the composition of the invention contains silicone conditioning agents. Preferably, these are emulsified droplets of a silicone conditioning agent. These are for enhancing conditioning performance.
  • Suitable silicones include polydiorganosiloxanes, in particular polydimethylsiloxanes, which have the PCPC designation dimethicone.
  • composition of the invention are polydimethyl siloxanes having hydroxyl end groups, which have the PCPC designation dimethiconol.
  • silicone gums having a slight degree of cross-linking are described for example in WO 96/31188.
  • the viscosity of the emulsified silicone itself is typically at least 10,000 cSt at 25°C.
  • the viscosity of the silicone itself is preferably at least 60,000 cSt, most preferably at least 500,000 cSt, ideally at least 1,000,000 cSt.
  • the viscosity does not exceed 1x109 cSt for ease of formulation.
  • Emulsified silicones for use in the composition of the invention will typically have an average silicone droplet size in the composition of less than 30, preferably less than 20, more preferably less than 10 micron, ideally from 0.01 to 1 micron.
  • Silicone emulsions having an average silicone droplet size of less than 0.15 micron are generally termed microemulsions.
  • Silicone particle size may be measured by means of a laser light scattering technique, for example using a 2600D Particle Sizer from Malvern Instruments.
  • suitable pre-formed emulsions include Xiameter MEM 1785 and microemulsion DC2-1865 available from Dow Corning. These are emulsions / microemulsions of dimethiconol.
  • cross-linked silicone gums are also available in a pre-emulsified form, which is advantageous for ease of formulation.
  • a further preferred class of silicones for inclusion in the composition of the invention are amino functional silicones.
  • amino functional silicone is meant a silicone containing at least one primary, secondary or tertiary amine group, or a quaternary ammonium group.
  • suitable amino functional silicones include polysiloxanes having the PCPC designation "amodimethicone”.
  • Specific examples of amino functional silicones suitable for use in the composition of the invention are the aminosilicone oils DC2-8220, DC2-8166 and DC2-8566 (all ex Dow Corning). Suitable quaternary silicone polymers are described in EP-A-0530974.
  • a preferred quaternary silicone polymer is K3474, ex Goldschmidt.
  • emulsions of amino functional silicone oils with non-ionic and/or cationic surfactants are also suitable.
  • Pre-formed emulsions of amino functional silicones are also available from suppliers of silicone oils such as Dow Corning and General Electric. Specific examples include DC939 Cationic Emulsion and the non-ionic emulsions DC2-7224, DC2- 8467, DC2-8177 and DC2-8154 (all ex Dow Corning). Combination of amino and non-amino functional silicones may also be used.
  • the total amount of silicone is preferably from 0.01 wt.-% to 10 wt.-% of the total composition, more preferably from 0.1 wt.-% to 5 wt.-%, most preferably from 0.5 wt.- % to 3 wt.-%.
  • the composition of the invention comprises a preservative or preservative system.
  • suitable preservatives include benzyl alcohol, phenoxyethanol, parabens, benzoic acid/sodium benzoate, sorbic acid/potassium sorbate, and other organic acids used to provide antimicrobial protection.
  • the composition comprises from 0.01 to 5 wt.- %, particularly preferably from 0.05 to 1 wt.-% of at least one preservative.
  • the preservative is selected from the group consisting of phenoxyethanol, benzyl paraben, butyl paraben, ethyl paraben, isobutyl paraben, isopropyl paraben, methyl paraben, propyl paraben, iodopropynyl butylcarbamate, methyldibromoglutaronitrile, DMDM hydantoin and combinations thereof.
  • the composition comprises a preservative selected from the group consisting of cetyltrimethyl ammonium chloride, cetylpyridinium chloride, benzethonium chloride, diisobutylethoxyethyldimethyl benzylammonium chloride, sodium N-lauryl sarcosinate, sodium-N-palmethylsarcosinate, lauroylsarcosine, N- myristoylglycine, potassium-N-laurylsarcosine, trimethylammonium chloride, sodium aluminium chlorohydroxylactate, triethylcitrate, tricetylmethylammonium chloride, 2,4,4'-trichloro-2'-hydroxydiphenylether (Triclosan), phenoxyethanol, 3,4,4'- trichlorocarbanilide (Triclocarban), diaminoalkylamide, L-lysine hexadecylamide, heavy metal citrate salts, zinc salt
  • the preservative is selected from the group consisting of phenoxyethanol, benzyl paraben, butyl paraben, ethyl paraben, isobutyl paraben, isopropyl paraben, methyl paraben, propyl paraben, iodopropynyl butylcarbamate, methyldibromoglutaronitrile, DMDM hydantoin and combinations thereof.
  • the composition of the invention is substantially free of parabens.
  • the composition of the invention comprises an anti- dandruff agent such as piroctone olamine.
  • composition of the invention may also comprise a dispersed, non-volatile, water- insoluble oily conditioning agent.
  • insoluble is meant that the material is not soluble in water (distilled or equivalent) at a concentration of 0.1 % (w/w), at 25°C.
  • Suitable oily or fatty materials are selected from hydrocarbon oils, fatty esters and mixtures thereof. Straight chain hydrocarbon oils will preferably contain from about 12 to about 30 carbon atoms. Also suitable are polymeric hydrocarbons of alkenyl monomers, such as C2-C6 alkenyl monomers.
  • hydrocarbon oils include paraffin oil, mineral oil, saturated and unsaturated dodecane, saturated and unsaturated tridecane, saturated and unsaturated tetradecane, saturated and unsaturated pentadecane, saturated and unsaturated hexadecane, and mixtures thereof.
  • Branched-chain isomers of these compounds, as well as of higher chain length hydrocarbons, can also be used.
  • Suitable fatty esters are characterised by having at least 10 carbon atoms, and include esters with hydrocarbyl chains derived from fatty acids or alcohols.
  • Monocarboxylic acid esters include esters of alcohols and/or acids of the formula R'COOR in which R' and R independently denote alkyl or alkenyl radicals and the sum of carbon atoms in R' and R is at least 10, preferably at least 20.
  • Di- and trialkyl and alkenyl esters of carboxylic acids can also be used.
  • Particularly preferred fatty esters are mono-, di- and triglycerides, more specifically the mono-, di-, and tri-esters of glycerol and long chain carboxylic acids such as C 8 -C22 carboxylic acids.
  • Preferred materials include cocoa butter, palm stearin, sunflower oil, soybean oil and coconut oil.
  • the oily or fatty material may be present at a level of from 0.05 to 10 wt.-%, preferably from 0.2 to 5 wt.-%, more preferably from 0.5 to 3 wt.-%, based on the total weight of the composition.
  • the composition of the invention is a shampoo composition.
  • the shampoo composition comprises from 1 to 99%, preferably from 5 to 95%, more preferably from 10 to 90% by weight of the total composition of water, and from 0.1 to 99%, preferably from 1 to 95%, more preferably from 5 to 90%, often from 5 to 25% by weight of the total composition of a cleansing surfactant.
  • Suitable cleansing surfactants are generally anionic, amphoteric, betaine, or zwitterionic surfactants.
  • the anionic surfactants are alkyl ether or alkyl ether sulfates, such as sodium lauryl sulfate, or other compounds described above.
  • the shampoo composition comprises one or more further cosmetically acceptable components (F), which can be present in an amount of at least 0.5% by weight, or from 0.5 to 20% by weight, by total weight of the shampoo composition.
  • the component (F) is selected from the group consisting of cleansing ingredients, acidity regulators, colorants, conditioning agents, emulsifiers, film formers, fragrances, glossers, humectants, lubricants, moisturizers, pigments, preservatives, hair penetration enhancers, scalp actives, stabilizers, surfactants, thickeners, viscosity modifiers, and combinations thereof. More preferably, the component (F) is selected from the group consisting of surfactants, viscosity- modifying polymers and conditioning ingredients.
  • the shampoo composition comprises from 1 wt.-% to 20 wt.-% (preferably from 1 wt.-% to 5 wt.-%) of the compound according to Formula (I) of the present invention, and at least 0.5% by weight of one or more further components (F) selected from the group consisting of surfactants, polymers, conditioning agents, actives, acidity regulators, lubricants, moisturizers, oils, preservatives, sequestrants, strengtheners, sun protectors, and combinations thereof.
  • the shampoo composition comprises further cosmetically acceptable components (F) being cleansing ingredients.
  • the shampoo composition comprises from 0.05 to 20% by weight of cleansing ingredients, based on the total weight of the shampoo composition.
  • the level of cleansing ingredient is from 1% to 20% by weight, preferably from 5% to 18%, more preferably from 8% to 16%, based on the total weight of the shampoo composition.
  • the cleansing ingredient is selected from the group consisting of non-polymeric surfactants, saponins, polymeric surfactants, and combinations thereof.
  • the cleansing ingredient comprises or consists of surfactants.
  • the shampoo composition comprises from 1 wt.-% to 20 wt.-% (preferably from 1 wt.-% to 5 wt.-%) of the compound according to Formula (I) of the present invention, and at least 0.5 % by weight of surfactants, preferably cleansing anionic or non-ionic surfactants, such as sodium laureth sulphate, sodium lauryl sulphate, ammonium laureth sulphate, ammonium lauryl sulphate, olefin sulfonates, olefin sulfates, laureth-3 or 4, cocamide DEA, glucosides, cocamidopropyl betaine, coco betaine, cocoamphodipropionate, sodium methyl 2-sulfolaurate and other laurates, sulfoacetates, sulfosuccinates, lactylates, sultaines, caprylates/ caprates, isethionates,
  • surfactants
  • the shampoo composition comprises sophorolipids and/or rhamnolipids.
  • the shampoo composition is silicone-free.
  • the shampoo composition is sulfate-free.
  • the shampoo composition is silicone-free and sulfate-free.
  • the shampoo composition comprises, based on the total weight of the shampoo composition: (i) from 1 wt.-% to 20 wt.-% (preferably from 1 wt.-% to 5 wt.-%) of the compound according to Formula (I) of the present invention; (ii) from 5 wt.-% to 20 wt.-% of one or more anionic surfactants; (iii) at least 50 wt.-% water; and (iv) at least one further cosmetically acceptable component (F) selected from the group consisting of silicone, cationic polymer, rheology modifiying agent, and an amphoteric or zwitterionic surfactant.
  • the shampoo composition comprises, based on the total weight of the shampoo composition: (i) from 1 wt.-% to 20 wt.-% (preferably from 1 wt.-% to 5 wt.-%) of the compound according to Formula (I) of the present invention; (ii) from 5 wt.-% to 20 wt.-% of one or more anionic surfactants; (iii) at least 50 wt.-% water; (iv) at least one further component selected from the group consisting of silicone, cationic polymer, rheology modifiying agent, and an amphoteric or zwitterionic surfactant; and (v) at least one further cosmetically acceptable component (F).
  • the shampoo composition consists of, based on the total weight of the shampoo composition: (i) from 1 wt.-% to 20 wt.-% (preferably from 1 wt.-% to 5 wt.-%) of the compound according to Formula (I) of the present invention; (ii) from 5 wt.-% to 20 wt.-% of one or more anionic surfactants; (iii) at least 50 wt.-% water; (iv) at least one further component selected from the group consisting of silicone, cationic polymer, rheology modifiying agent, and an amphoteric or zwitterionic surfactant; and (v) at least one further cosmetically acceptable component (F) selected from the group consisting of conditioning agents, such as panthenol, panthenyl ethyl ether, proteins, hydrolysed proteins (preferably of vegetable or animal origin, for example hydrolysed collagen or hydrolysed keratin), nutrients; antioxidants, such as vitamin E
  • the composition of the present invention is a fabric care composition.
  • the composition of the invention is selected from the group consisting of laundry detergent composition, fabric conditioner composition, and fabric spray.
  • the laundry detergent composition may, for example, be in liquid or solid form.
  • the laundry detergent composition may, for example, be in the form of a liquid, a gel, a powder, or granules.
  • the laundry detergent composition preferably comprises one or more surfactants, which are preferably selected from anionic, nonionic, cationic and zwitterionic surfactants. Examples of surfactants are described further above.
  • the laundry detergent composition may also comprise a polymer.
  • the laundry detergent composition may also comprise a solvent, for example water.
  • the fabric conditioner composition may, for example, be in liquid or solid form.
  • the fabric conditioner composition may, for example, be in the form of a liquid, a gel, a powder, or granules.
  • the fabric conditioner composition preferably comprises a cationic softening agent, which is preferably a quaternary ammonium compound.
  • the fabric conditioner composition may also comprise a solvent, for example water.
  • the composition of the invention can be manufactured by methods known in the art.
  • the composition of the invention can be manufactured by mixing its ingredients.
  • the compound according to Formula (I) of the present invention can be mixed with the other ingredients of the composition of the invention.
  • the present invention also relates to the use of a compound according to Formula (I) of the present invention as a hair care agent, preferably a hair repair agent, a hair strengthening agent or a hair conditioning agent, or as a fabric care agent, preferably a fabric repair agent, a fabric strengthening agent or a fabric conditioning agent.
  • the present invention also relates to the use of a compound according to Formula (I) of the present invention as a hair care agent.
  • the compound according to Formula (I) is used as a hair repair agent, a hair strengthening agent or a hair conditioning agent.
  • the compound according to Formula (I) is used as a hair repair agent or a hair strengthening agent.
  • the compound according to Formula (I) is used as a hair conditioning agent.
  • the present invention also relates to the use of a compound according to Formula (I) of the present invention as a fabric care agent.
  • the compound according to Formula (I) is used as a fabric repair agent, a fabric strengthening agent or a fabric conditioning agent.
  • the compound according to Formula (I) is used as a fabric repair agent or a fabric strengthening agent.
  • the compound according to Formula (I) is used as a fabric conditioning agent.
  • the present invention also relates to a method for treating hair, comprising a step a) and optionally a step b): Step a): Applying to the hair a composition comprising a compound according to Formula (I) of the present invention; Step b): Applying to the hair a composition selected from a hair bleaching composition, a hair lightening composition, a hair coloring composition, a hair highlighting composition, a hair curling composition, a hair waving composition, a hair straightening composition; wherein step b), if present, is preferably performed before, during or after step a).
  • the composition comprising a compound according to Formula (I) can be applied to the hair in a usual manner.
  • step b) the composition selected from a hair bleaching composition, a hair lightening composition, a hair coloring composition, a hair highlighting composition, a hair curling composition, a hair waving composition, a hair straightening composition can be applied to the hair in a usual manner.
  • the composition used in step b) is selected from a hair bleaching composition, a hair lightening composition, a hair coloring composition, a hair highlighting composition.
  • the composition used in step b) is selected from a hair curling composition, a hair waving composition, a hair straightening composition.
  • step b) is not present.
  • step b) is present.
  • step b) is performed before step a).
  • step b) is performed during step a). In another embodiment, step b) is performed after step a).
  • the present invention also relates to a method for treating fabric, comprising the following step: Applying to the fabric a composition comprising a compound according to Formula (I) of the present invention.
  • the fabric may, for example, be a woven fabric or a non-woven fabric.
  • the fibre making up the fabric may be or may include natural or synthetic fibres including polyamides, particularly natural polyamides such as silk or wool or synthetic polyamides such as nylon or elastane, cellulosic fibres such as cotton, linen or rayon, synthetic polymers such as polyesters, particularly polyethylene terephthalate, or acetate polymers. Keratin-containing fabrics are particularly preferred.
  • the present invention also relates to a kit comprising (i) a composition comprising a compound according to Formula (I) of the present invention; and (ii) a composition selected from a hair bleaching composition, a hair lightening composition, a hair coloring composition, a hair highlighting composition, a hair curling composition, a hair waving composition, a hair straightening composition.
  • the kit comprises (i) a composition comprising a compound according to Formula (I) of the present invention; and (ii) a composition selected from a hair bleaching composition, a hair lightening composition, a hair coloring composition, a hair highlighting composition.
  • the kit comprises (i) a composition comprising a compound according to Formula (I) of the present invention; and (ii) a composition selected from a hair curling composition, a hair waving composition, a hair straightening composition.
  • the present invention is illustrated by the following examples without being limited thereby.
  • Example 1 Examples 2 and 3: Example 4: Examples 5 and 6: Example 7: General procedure for the preparation of the compounds according to Formula 1: In a suitably sized 4-neck round bottom flask, equipped with an overhead stirrer, a thermometer/pH meter and a connection to an automated liquid dispensing unit, water (A g, see table 1) is added and cooled down to 4 °C. Under constant stirring, the desired diamine (B g, 1 equiv., see table 1) is then added during over a period of 20 to 30 minutes taking care that the internal temperature is kept at around 10 and 20 °C.
  • a g see table 1
  • B g desired diamine
  • Example 8 In Examples 8 and 9, Compound A refers to the following compound according to the invention: In Examples 8 and 9, Compound B refers to the following compound according to the invention:
  • Example 8 ⁇ Shampoo composition (%a.m. refers to % active material) Preparation: Add the water to the vessel. Premix the chelating agent Disodium EDTA to the water and stir until clear. Add the sodium laureth sulfate. Slowly stir until homogenous and add the cocoamidopropyl betaine. Add the rest of the ingredients in order. Adjust to pH around 6.0 with citric acid. Adjust viscosity and pH to spec.
  • Example 9 ⁇ Hair conditioner composition (%a.m.
  • Preparation Add the water to the vessel and begin to stir. Start to heat to 80 - 85 °C. Add the fats and cationic systems and stir until melted. Homogenise at 3000 rpm until smooth and white. Cool to below 40 °C and add the remaining ingredients in order. Adjust pH with citric acid to 4,0 to 4,5.
  • Examples 10 to 12 Compound C refers to the following compound according to the invention: In Examples 10 to 12, Compound D refers to the following compound according to the invention: Example 10 ⁇ Protein integrity Materials: Hair type: Caucasian Virgen Hair Tresses Color Code 5/0 (Supplier: Kerling International Haarfabrik GmbH, Backnang, Germany) - 3 hair tresses used per treatment Equipment: DSC-TGA SDT-Q600, TA Instruments (USA) DSC Method: Differential Scanning Calorimetry (DSC) of human hair in water is a well suited and readily applied method for the investigation of changes of hair keratin caused by environmental influences.
  • DSC Differential Scanning Calorimetry
  • Denaturation enthalpy is a measure for the amount and state of Intermediate Filaments (IFs).
  • Denaturation temperature gives information about the changes in the amorphous IF Associated Proteins (IFAPs).
  • Example 10 Caucasian virgin hair tresses were bleached, then soaked in a 1% solution of the respective sample in water for 30 min, then washed twice with a 14% solution of sodium laureth sulfate in water, then dried, and then analyzed using DSC.
  • Example 11 External Fibre Action (smoothness) Materials: Hair type: Caucasian Virgen Hair Tresses Color Code 5/0 (Supplier: Kerling International Haarfabrik GmbH, Backnang, Germany) - 3 hair tresses used per treatment (9 fibers per treatment) Equipment: SEM Quanta FEG 650 (FEI – Thermo Fisher Scientific, US) SEM Method: After hair tresses treatment with target formulation and/or ingredient, hair fibers are collected without direct contact with hands and prepared to be evaluated through SEM.
  • Hair fibers from the tresses are attached to a coated carbon and copper conductive tape, mounted on blades and coated under high vacuum with the BAL-TEC SCD 020 sputter coating machine using platinum as a metal target, plus a coating thickness measure system QSG060. Scanning of coated hair specimens is carried out using a SEM Quanta FEG 650 (FEI – Thermo Fisher Scientific, US) with tungsten filament, operating at reduced pressure, with scattered electron detectors (EDT). Sections of each shaft (around 3 cm in the middle of hair shaft) are scanned to ensure that changes seen are uniform. Magnification: 500x and 3000x.
  • Example 11a Caucasian virgin hair tresses were bleached, then soaked in a 1% solution of the respective sample in water for 30 min, then washed twice with a 14% solution of sodium laureth sulfate in water, and then dried. Hair fibers from these hair tresses were analyzed using SEM. Virgin hair fibers (without the above treatment) were analyzed as well. * Bleached, soaked, washed, dried as described above Example 11b Curly virgin hair tresses were straightened, then soaked in a 1% solution of the respective sample in water for 30 min, then washed twice with a 14% solution of sodium laureth sulfate in water, and then dried. Hair fibers from these hair tresses were analyzed using SEM.
  • Spectral range 540 to 4000 cm-1
  • FTIR Method After hair tresses treatment with target formulation and/or ingredient, hair fibers are collected without direct contact with hands and prepared to be evaluated through FTIR. The hair tress is added in contact with crystal. The spectrum of the sample was recorded in FTIR spectrometer in the range of 4000 cm-1 to 540 cm-1 at room temperature. Each measurement is repeated to ensure the reproducibility of the spectra.
  • the incident IR beam strikes the interface between the IRE and the hair sample of a lower refractive index. This internal reflectance creates an evanescent wave that extends beyond the surface of the crystal into the hair sample held in contact with the crystal.
  • This evanescent wave protrudes only a few microns (0.5 to 5) beyond the crystal surface and into the sample.
  • the sample absorbs IR radiation at certain frequencies; the evanescent wave will be attenuated in regions of the infrared spectrum where the sample absorbs energy.
  • This attenuated IR radiation of evanescent wave is passed back to the IR beam, which then exits the opposite end of the crystal and it is detected by the detector in the IR spectrometer and the system generates an infrared spectrum.
  • the spectral recordings are done at 32 scans with resolution of 4 cm ⁇ 1. Data area is analyzed by using statistical Perkin Elmer Version 10.03.09.
  • Descriptive data that include mean, standard deviation, t-values and p-values are calculated for pre- and post-treatment of the material used for analysis.
  • FT-IR Fourier Transform Infrared
  • Example 12a Caucasian virgin hair tresses were bleached, then soaked in a 1% solution of the respective sample in water for 30 min, then washed twice with a 14% solution of sodium laureth sulfate in water, then dried, and then analyzed using a FT-IR spectrometer. Virgin hair tresses (without the above treatment) were analyzed as well. * Bleached, soaked, washed, dried as described above

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Abstract

La présente invention concerne des composés qui sont appropriés en tant qu'agents de réparation capillaire ou agents de réparation de tissu, des compositions et des kits comprenant de tels composés, l'utilisation de tels composés en tant qu'agents de réparation capillaire ou agents de réparation de tissu, et des méthodes de traitement des cheveux ou du tissu.
PCT/EP2023/052239 2022-02-02 2023-01-31 Composés destinés à être utilisés en tant qu'agents de réparation capillaire ou agents de réparation de tissu WO2023148138A1 (fr)

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CN117586143A (zh) * 2024-01-18 2024-02-23 广州同隽医药科技有限公司 聚醚酰胺、其制备方法及其在头发损伤修复中的应用

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US3962418A (en) 1972-12-11 1976-06-08 The Procter & Gamble Company Mild thickened shampoo compositions with conditioning properties
US4009256A (en) 1973-11-19 1977-02-22 National Starch And Chemical Corporation Novel shampoo composition containing a water-soluble cationic polymer
US4529773A (en) 1982-03-17 1985-07-16 David Witiak Alkali-soluble emulsion polymers in acidic surfactant compositions
WO1992006154A1 (fr) 1990-09-28 1992-04-16 The Procter & Gamble Company Tensioactifs d'amides de l'acide gras de polyhydroxy destines a ameliorer l'efficacite des enzymes
EP0530974A1 (fr) 1991-08-05 1993-03-10 Unilever Plc Compositions pour le soin des cheveux
US5194639A (en) 1990-09-28 1993-03-16 The Procter & Gamble Company Preparation of polyhydroxy fatty acid amides in the presence of solvents
WO1995022311A1 (fr) 1994-02-18 1995-08-24 Unilever Plc Compositions de detersif pour soins corporels
WO1996031188A1 (fr) 1995-04-06 1996-10-10 Unilever Plc Compositions pour traitement capillaire
WO2013178700A2 (fr) 2012-05-30 2013-12-05 Clariant International Ltd. Composition contenant de la n-méthyl-n-acylglucamine
EP3061499A1 (fr) * 2015-02-26 2016-08-31 The Procter and Gamble Company Procédé pour fournir des effets visuels sur des fibres
EP3001809B1 (fr) 2013-08-01 2017-07-12 Liqwd, Inc. Procédés de conditionnement capillaire et cutané

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3958581A (en) 1972-05-17 1976-05-25 L'oreal Cosmetic composition containing a cationic polymer and divalent metal salt for strengthening the hair
US3962418A (en) 1972-12-11 1976-06-08 The Procter & Gamble Company Mild thickened shampoo compositions with conditioning properties
US4009256A (en) 1973-11-19 1977-02-22 National Starch And Chemical Corporation Novel shampoo composition containing a water-soluble cationic polymer
US4529773A (en) 1982-03-17 1985-07-16 David Witiak Alkali-soluble emulsion polymers in acidic surfactant compositions
US5194639A (en) 1990-09-28 1993-03-16 The Procter & Gamble Company Preparation of polyhydroxy fatty acid amides in the presence of solvents
WO1992006154A1 (fr) 1990-09-28 1992-04-16 The Procter & Gamble Company Tensioactifs d'amides de l'acide gras de polyhydroxy destines a ameliorer l'efficacite des enzymes
EP0550637A1 (fr) 1990-09-28 1993-07-14 Procter & Gamble Preparation d'amides de l'acide gras de polyhydroxy en presence de solvants.
EP0530974A1 (fr) 1991-08-05 1993-03-10 Unilever Plc Compositions pour le soin des cheveux
WO1995022311A1 (fr) 1994-02-18 1995-08-24 Unilever Plc Compositions de detersif pour soins corporels
WO1996031188A1 (fr) 1995-04-06 1996-10-10 Unilever Plc Compositions pour traitement capillaire
WO2013178700A2 (fr) 2012-05-30 2013-12-05 Clariant International Ltd. Composition contenant de la n-méthyl-n-acylglucamine
EP3001809B1 (fr) 2013-08-01 2017-07-12 Liqwd, Inc. Procédés de conditionnement capillaire et cutané
EP3061499A1 (fr) * 2015-02-26 2016-08-31 The Procter and Gamble Company Procédé pour fournir des effets visuels sur des fibres

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117586143A (zh) * 2024-01-18 2024-02-23 广州同隽医药科技有限公司 聚醚酰胺、其制备方法及其在头发损伤修复中的应用
CN117586143B (zh) * 2024-01-18 2024-04-30 广州同隽医药科技有限公司 聚醚酰胺、其制备方法及其在头发损伤修复中的应用

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