# US 12,453,691 B2 · Composition comprising hyaluronic acid-based polyion complex particle > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,453,691 B2 - Document ID: US12453691B2 - Status: Granted - Kind: B2 - Application number: 17/785,019 - Filed: 2020-12-04 - Published: 2023-02-16 - Granted: 2025-10-28 - Earliest claimed: 2019-12-17 - Assignees: L'oreal - Applicants: L'Oreal - Inventors: Toshifumi Shiroya; Tatsushi Isojima; Mariko Yamamoto; Takehiko Kasai; Kazuhiko Maruyama; Shinobu Mitsuda - Web page: https://patentgrep.com/patent/US12453691B2 ## CPC - A61K 8/735: {Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof} - A61Q 19/00: Preparations for care of the skin - A61K 8/0204: {Specific forms not provided for by any of groups A61K8/0208 - A61K8/14} - A61K 8/0241: {Containing particulates characterized by their shape and/or structure (see also A61K8/04, A61K8/11, and A61K8/14, further aspects are classified in A61K2800/40 and subcodes)} - A61K 8/34: Alcohols - A61K 8/55: Phosphorus compounds - A61K 8/64: Proteins; Peptides; Derivatives or degradation products thereof - A61Q 19/007: {Preparations for dry skin} - A61Q 19/08: Anti-ageing preparations - A61K 2800/5424: anionic - A61K 2800/5426: cationic - A61K 2800/5428: amphoteric or zwitterionic - A61K 2800/95: Involves in-situ formation or cross-linking of polymers - 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) - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS ## Abstract The present invention relates to a composition comprising: (a) at least one particle comprising at least one cationic polymer and at least one anionic polymer, at least one cationic polymer and at least one amphoteric polymer, at least one anionic polymer and at least one amphoteric polymer, or at least one amphoteric polymer, and at least one non-polymeric acid having two or more pKa values or salt(s) thereof or at least one non-polymeric base having two or more pKb values or salt(s) thereof; and (b) water, wherein the anionic polymer is selected from hyaluronic acid and derivatives thereof, and the amphoteric polymer is selected from cationized hyaluronic acid and salts thereof. The composition according to the present invention is stable, and can have a variety of cosmetic functions. The stickiness of the composition according to the present invention can be reduced. ## Claims ### Claim 1 A composition, comprising: (a) at least one particle, comprising at least one cationic polymer and at least one anionic polymer, at least one cationic polymer and at least one amphoteric polymer, at least one anionic polymer and at least one amphoteric polymer, or at least one amphoteric polymer, and at least one non-polymeric acid having two or more pKa values or salt(s) thereof or at least one non-polymeric base having two or more pKb values or salt(s) thereof; and (b) water, wherein the anionic polymer is selected from hyaluronic acid, and esters and salts thereof, and the amphoteric polymer is selected from cationized hyaluronic acid and salts thereof. ### Claim 2 (depends on 1) The composition according to claim 1, wherein the cationized hyaluronic acid has at least one quaternary ammonium group-containing group and has a degree of cationization of 0.05 to 0.6. ### Claim 3 (depends on 1) The composition according to claim 1, wherein the cationic polymer has at least one positively chargeable and/or positively charged moiety selected from the group consisting of a secondary or tertiary amino group, a quaternary ammonium group, a guanidine group, a biguanide group, an imidazole group, an imino group, a pyridyl group, and an amino group. ### Claim 4 (depends on 1) The composition according to claim 1, wherein the cationic polymer is selected from the group consisting of cyclopolymers of alkyldiallylamine and cyclopolymers of dialkyldiallylammonium comprises (co)polydiallyldialkyl ammonium chloride, (co)polyamines comprises (co)polylysines, cationic (co)polyaminoacids such as collagen, cationic cellulose polymers, and salts thereof. ### Claim 5 (depends on 1) The composition according to claim 1, wherein the total amount of the cationic and/or anionic and/or amphoteric polymer(s) forming the (a) particle in the composition is from 0.01% to 15% by weight, relative to the total weight of the composition. ### Claim 6 (depends on 1) The composition according to claim 1, wherein the nonpolymeric acid having two or more pKa values or salt(s) thereof is an organic acid or salt(s) thereof. ### Claim 7 (depends on 1) The composition according to claim 1, wherein the amount of the non-polymeric acid having two or more pKa values or salt(s) thereof or non-polymeric base having two or more pKb values or salt(s) thereof in the composition is from 0.01% to 15% by weight, relative to the total weight of the composition. ### Claim 8 (depends on 1) The composition according to claim 1, wherein the amount of the (a) particle in the composition is from 0.01% to 30% by weight, relative to the total weight of the composition. ### Claim 9 (depends on 1) The composition according to claim 1, wherein the amount of the (b) water in the composition is from 50% to 99.9% by weight, relative to the total weight of the composition. ### Claim 10 (depends on 1) The composition according to claim 1, wherein the pH of the composition is from 3 to 9. ### Claim 11 (depends on 1) The composition according to claim 1, wherein the composition further comprises (c) at least one oil. ### Claim 12 (depends on 1) The composition according to claim 1, wherein the composition is a cosmetic composition. ### Claim 13 (depends on 1) A process for preparing a film, comprising: applying onto a substrate the composition according to claim 1; and drying the composition. ### Claim 14 (depends on 1) A film prepared by a process comprising: applying onto a substrate the composition according to claim 1; and drying the composition. ### Claim 15 A film comprising: at least one cationic polymer and at least one anionic polymer, at least one cationic polymer and at least one amphoteric polymer, at least one anionic polymer and at least one amphoteric polymer, or at least one amphoteric polymer; at least one non-polymeric acid having two or more pKa values or salt(s) thereof or at least one non-polymeric base having two or more pKb values or salt(s) thereof; and optionally at least one oil, wherein the anionic polymer is selected from hyaluronic acid and esters and salts thereof; and the amphoteric polymer is selected from cationized hyaluronic acid and salts thereof. ### Claim 16 (depends on 1) A cosmetic process for a keratin substance such as skin, comprising applying to the keratin substance the composition according to claim 1; and drying the composition to form a cosmetic film on the keratin substance.