# US 11,433,014 B2 · Polyol polyrhamnosides, process for the preparation thereof, and cosmetic and/or pharmaceutical composition comprising same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,433,014 B2 - Document ID: US11433014B2 - Status: Granted - Kind: B2 - Application number: 16/772,364 - Filed: 2018-11-27 - Published: 2021-12-16 - Granted: 2022-09-06 - Earliest claimed: 2017-12-12 - Assignees: Societe D'Exploitation De Produits Pour Les Industries Chimiques Seppic - Applicants: Societe D'Exploitation De Produits Pour Les Industries Chimiques Seppic - Inventors: Georges Manuel Dacosta; Jérome Guilbot; Stéphane Dessilla; Laetitia Cattuzzato - Web page: https://patentgrep.com/patent/US11433014B2 ## CPC - A61K 8/602: {Glycosides, e.g. rutin} - A61K 8/73: Polysaccharides - A61K 8/345: {containing more than one hydroxy group} - A61K 8/4973: {with oxygen as the only hetero atom} - A61K 8/60: Sugars; Derivatives thereof - A61K 31/40: having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil - A61K 31/422: not condensed and containing further heterocyclic rings - A61K 31/427: not condensed and containing further heterocyclic rings - A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465) - A61K 31/4725: containing further heterocyclic rings - A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca - A61P 17/00: Drugs for dermatological disorders - A61Q 1/14: Preparations for removing make-up - A61Q 5/02: Preparations for cleaning the hair - A61Q 19/00: Preparations for care of the skin - A61Q 19/007: {Preparations for dry skin} - C07D 307/20: Oxygen atoms - C07H 15/04: attached to an oxygen atom of the saccharide radical - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13) ## Abstract Disclosed is a composition based on a polyol of formula: HO—CH2—(CHOH)m—CH2—OH and on alkyl polyrhamnosides of formula: HO—CH2—(CHOH)m—CH2—O-(Rham)x-H; process for preparing same, and cosmetic or pharmaceutical composition including same. ## Claims ### Claim 1 A composition (C1) comprising, per 100% of mass: (1)—an amount of greater than 0% by mass and less than or equal to 25% by mass of a polyol of formula (I): HO—CH2—(CHOH)m—CH2—OH (I); in which formula (I) m represents an integer equal to 2, 3 or 4; (2)—an amount of greater than 0% by mass and less than or equal to 30% by mass of one or more anhydrides of said polyol of formula (I); (3)—from 60% by mass to 95% by mass of a composition (CR) represented by formula (II): HO—CH2—(CHOH)m—CH2—O-(Rham)X—H (II), in which formula (II) Rham represents a rhamnose residue, m is as defined in formula (I) and x, which indicates the average degree of polymerization of said Rham residue, represents a decimal number greater than 1.0 and less than or equal to 2.5; and (4)—an amount of greater than 0% by mass and less than or equal to 5% by mass of rhamnose. ### Claim 2 (depends on 1) The composition (C1) as defined in claim 1, wherein, in formulae (I) and (II), m represents the number 2. ### Claim 3 (depends on 1) The composition (C1) as defined in claim 1, wherein, in formulae (I) and (II), m represents the number 3. ### Claim 4 (depends on 3) The composition (C1) as defined in claim 3, comprising, per 100% of mass: (1)—from greater than zero up to 25% by mass of the compound of formula: HO—CH2—(CHOH)3—CH2—OH; (2)—from greater than zero up to 5% by mass of the compound of formula (B12): (3)—from 70% by mass to 95% by mass of a composition (CR3) represented by the formula HO—CH2—(CHOH)3—CH2—O-(Rham)x-H; and (4)—from greater than zero up to 2% by mass of rhamnose. ### Claim 5 (depends on 1) The composition (C1) as defined in claim 1, wherein, in formulae (I) and (II), m represents the number 4. ### Claim 6 (depends on 5) The composition (C1) as defined in claim 5, comprising, per 100% of mass: (1)—from greater than zero up to 25% by mass of the compound of formula: HO—CH2—(CHOH)4—CH2—OH; (2)—from greater than zero up to 30% by mass of the compound of formula (B13): alone or in combination with the compound of formula (B14): (3)—from 70% by mass to 95% by mass of a composition (CR4) represented by the formula: HO—CH2—(CHOH)4—CH2—O-(Rham)X—H; and (4)—from greater than zero up to 4% by mass of rhamnose. ### Claim 7 (depends on 6) The composition (C1) as defined in claim 6, comprising, per 100% of mass: (1)—from greater than zero up to 25% by mass of the compound of formula: HO—CH2—(CHOH)4—CH2—OH; (2)—from greater than zero up to 25% by mass of the compound of formula (B13); (2′)—from greater than zero up to 5% by mass of the compound of formula (B14); (3)—from 70% by mass to 95% by mass of a composition (CR4) represented by the formula: HO—CH2—(CHOH)4—CH2—O-(Rham)x-H; and (4)—from greater than zero up to 2% by mass of rhamnose. ### Claim 8 (depends on 1) A process for preparing the composition (C1) as defined in claim 1, comprising: a step a) of heating, with gentle stirring, the polyol of formula (I), until the polyol is brought to a higher temperature (T1) of at least 5° C. above a melting point of the polyol to form a molten medium; a step b) of dispersing, with stirring, rhamnose monohydrate in the previously molten medium in a desired stoichiometric ratio to form a liquid medium; a step c) of acetalization by adding, with stirring, to the liquid medium obtained from step b), a catalytic amount of strong acid, while maintaining under partial vacuum and distilling off any water formed to form a solution; and a step d) of neutralizing the solution obtained on conclusion of step d), to obtain said composition (C1). ### Claim 9 (depends on 1) A topical cosmetic or dermocosmetic composition (C), comprising an effective amount of composition (C1) as defined in claim 1. ### Claim 10 (depends on 1) A topical pharmaceutical or dermopharmaceutical composition (C′), comprising an effective amount of composition (C1) as defined in claim 1. ### Claim 11 (depends on 1) A process for preparing the composition (C1) as defined in claim 1, comprising: a step a) of heating, with gentle stirring, the polyol of formula (I), until the polyol is brought to a higher temperature (T1) of at least 5° C. above a melting point of the polyol to form a molten medium; a step b) of dispersing, with stirring, rhamnose monohydrate in the previously molten medium in a desired stoichiometric ratio to form a liquid medium; and a step c) of acetalization by adding, with stirring, to the liquid medium obtained from step b), a catalytic amount of strong acid, while maintaining under partial vacuum and distilling off any water formed to form a solution. ### Claim 12 (depends on 2) A process for preparing the composition (C1) as defined in claim 2, comprising: a step a) of heating, with gentle stirring, the polyol of formula (I), until the polyol is brought to a higher temperature (T1) of at least 5° C. above a melting point of the polyol to form a molten medium; a step b) of dispersing, with stirring, rhamnose monohydrate in the previously molten medium in a desired stoichiometric ratio to form a liquid medium; a step c) of acetalization by adding, with stirring, to the liquid medium obtained from step b), a catalytic amount of strong acid, while maintaining under partial vacuum and distilling off any water formed to form a solution; and a step d) of neutralizing the solution obtained on conclusion of step d), to obtain said composition (C1). ### Claim 13 (depends on 3) A process for preparing the composition (C1) as defined in claim 3, comprising: a step a) of heating, with gentle stirring, the polyol of formula (I), until the polyol is brought to a higher temperature (T1) of at least 5° C. above a melting point of the polyol to form a molten medium; a step b) of dispersing, with stirring, rhamnose monohydrate in the previously molten medium in a desired stoichiometric ratio to form a liquid medium; a step c) of acetalization by adding, with stirring, to the liquid medium obtained from step b), a catalytic amount of strong acid, while maintaining under partial vacuum and distilling off any water formed to form a solution; and a step d) of neutralizing the solution obtained on conclusion of step d), to obtain said composition (C1). ### Claim 14 (depends on 4) A process for preparing the composition (C1) as defined in claim 4, comprising: a step a) of heating, with gentle stirring, the polyol of formula (I), until the polyol is brought to a higher temperature (T1) of at least 5° C. above a melting point of the polyol to form a molten medium; a step b) of dispersing, with stirring, rhamnose monohydrate in the previously molten medium in a desired stoichiometric ratio to form a liquid medium; a step c) of acetalization by adding, with stirring, to the liquid medium obtained from step b), a catalytic amount of strong acid, while maintaining under partial vacuum and distilling off any water formed to form a solution; and a step d) of neutralizing the solution obtained on conclusion of step d), to obtain said composition (C1). ### Claim 15 (depends on 5) A process for preparing the composition (C1) as defined in claim 5, comprising: a step a) of heating, with gentle stirring, the polyol of formula (I), until the polyol is brought to a higher temperature (T1) of at least 5° C. above a melting point of the polyol to form a molten medium; a step b) of dispersing, with stirring, rhamnose monohydrate in the previously molten medium in a desired stoichiometric ratio to form a liquid medium; a step c) of acetalization by adding, with stirring, to the liquid medium obtained from step b), a catalytic amount of strong acid, while maintaining under partial vacuum and distilling off any water formed to form a solution; and a step d) of neutralizing the solution obtained on conclusion of step d), to obtain said composition (C1). ### Claim 16 (depends on 6) A process for preparing the composition (C1) as defined in claim 6, comprising: a step a) of heating, with gentle stirring, the polyol of formula (I), until the polyol is brought to a higher temperature (T1) of at least 5° C. above a melting point of the polyol to form a molten medium; a step b) of dispersing, with stirring, rhamnose monohydrate in the previously molten medium in a desired stoichiometric ratio to form a liquid medium; a step c) of acetalization by adding, with stirring, to the liquid medium obtained from step b), a catalytic amount of strong acid, while maintaining under partial vacuum and distilling off any water formed to form a solution; and a step d) of neutralizing the solution obtained on conclusion of step d), to obtain said composition (C1). ### Claim 17 (depends on 7) A process for preparing the composition (C1) as defined in claim 7, comprising: a step a) of heating, with gentle stirring, the polyol of formula (I), until the polyol is brought to a higher temperature (T1) of at least 5° C. above a melting point of the polyol to form a molten medium; a step b) of dispersing, with stirring, rhamnose monohydrate in the previously molten medium in a desired stoichiometric ratio to form a liquid medium; a step c) of acetalization by adding, with stirring, to the liquid medium obtained from step b), a catalytic amount of strong acid, while maintaining under partial vacuum and distilling off any water formed to form a solution; and a step d) of neutralizing the solution obtained on conclusion of step d), to obtain said composition (C1). ### Claim 18 (depends on 2) A process for preparing the composition (C1) as defined in claim 2, comprising: a step a) of heating, with gentle stirring, the polyol of formula (I), until the polyol is brought to a higher temperature (T1) of at least 5° C. above a melting point of the polyol to form a molten medium; a step b) of dispersing, with stirring, rhamnose monohydrate in the previously molten medium in a desired stoichiometric ratio to form a liquid medium; and a step c) of acetalization by adding, with stirring, to the liquid medium obtained from step b), a catalytic amount of strong acid, while maintaining under partial vacuum and distilling off any water formed to form a solution. ### Claim 19 (depends on 3) A process for preparing the composition (C1) as defined in claim 3, comprising: a step a) of heating, with gentle stirring, the polyol of formula (I), until the polyol is brought to a higher temperature (T1) of at least 5° C. above a melting point of the polyol to form a molten medium; a step b) of dispersing, with stirring, rhamnose monohydrate in the previously molten medium in a desired stoichiometric ratio to form a liquid medium; and a step c) of acetalization by adding, with stirring, to the liquid medium obtained from step b), a catalytic amount of strong acid, while maintaining under partial vacuum and distilling off any water formed to form a solution. ### Claim 20 (depends on 4) A process for preparing the composition (C1) as defined in claim 4, comprising: a step a) of heating, with gentle stirring, the polyol of formula (I), until the polyol is brought to a higher temperature (T1) of at least 5° C. above a melting point of the polyol to form a molten medium; a step b) of dispersing, with stirring, rhamnose monohydrate in the previously molten medium in a desired stoichiometric ratio to form a liquid medium; and a step c) of acetalization by adding, with stirring, to the liquid medium obtained from step b), a catalytic amount of strong acid, while maintaining under partial vacuum and distilling off any water formed to form a solution.