Preparation of polysaccharide betainate type compounds, compounds obtained, their use and compositions comprising them
AssigneeL'oreal
InventorsClaude Dubief, Marguerite Rinaudo, Rachel Auzely-Velty
Life of this patent
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Abstract
A process for preparing compounds from the polysaccharide betainate family, novel compounds so obtained, and their use in cosmetics or in dermatology, as well as the compositions, such as cosmetic or dermatological compositions, comprising said novel compounds.
Claims69
A process for preparing a compound of formula (I):
- 17
- in which:
- R1, R2, and R3, which may be identical or different, are chosen from linear and branched, saturated and unsaturated C1-C30 hydrocarbon radicals optionally interrupted by at least one hetero atom chosen from N, O, and S and/or optionally substituted with at least one radical chosen from —OH, halogen and C6-C22 aryl radicals;
- A is chosen from linear and branched, saturated and unsaturated divalent C1-C22 hydrocarbon radicals, optionally interrupted by at least one hetero atom chosen from N, O, and S, and/or optionally substituted with at least one hydroxyl radical;
- X− is an anion deriving from an acid chosen from mineral and organic acids;
- and
- Y is a polysaccharide residue;
- comprising:
- reacting a polysaccharide with an N,N-dialkylaminocarboxylic acid of formula (II):
- 18
- in the presence of at least one reaction activator;
- and
- quaternizing the ester formed using a quaternization agent.
A process for preparing a compound of formula (I):
- 19
- in which:
- R1, R2, and R3, which may be identical or different, are chosen from linear and branched, saturated and unsaturated C1-C30 hydrocarbon radicals optionally interrupted by at least one hetero atom chosen from N, O, and S and/or optionally substituted with at least one radical chosen from —OH, halogen and C6-C22 aryl radicals;
- A is chosen from linear and branched, saturated and unsaturated divalent C1-C22 hydrocarbon radicals, optionally interrupted by at least one hetero atom chosen from N, O, and S, and/or optionally substituted with at least one hydroxyl radical;
- X− is an anion deriving from an acid chosen from mineral and organic acids;
- and
- Y is a polysaccharide residue;
- comprising:
- reacting a polysaccharide with a salt of an N,N,N-trialkylammoniocarboxylic acid of formula (III):
- 20
- wherein the reaction is carried out in a polar aprotic solvent;
- and the reaction takes place in the presence of at least one reaction activator.
A compound of formula (I):
- 21
- in which:
- R1, R2, and R3, which may be identical or different, are chosen from linear and branched, saturated and unsaturated C1-C30 hydrocarbon radicals optionally interrupted by at least one hetero atom chosen from N, O, and S and/or optionally substituted with at least one radical chosen from —OH, halogen and C6-C22 aryl radicals;
- A is chosen from linear and branched, saturated and unsaturated divalent C1-C22 hydrocarbon radicals, optionally interrupted by at least one hetero atom chosen from N, O, and S, and/or optionally substituted with at least one hydroxyl radical;
- X− is an anion deriving from an acid chosen from mineral and organic acids;
- and
- Y is a polysaccharide residue;
- excluding compounds of formula (I) in which Y represents a polymeric starch structure, A is —CH2—, and R1=R2=R3=—CH3.
A composition, in a cosmetic or dermatological acceptable medium, comprising at least one compound chosen from compounds of formula (I):
- 22
- in which:
- R1, R2, and R3, which may be identical or different, are chosen from linear and branched, saturated and unsaturated C1-C30 hydrocarbon radicals optionally interrupted by at least one hetero atom chosen from N, O, and S and/or optionally substituted with at least one radical selected from —OH, halogen and C6-C22 aryl radicals;
- A is chosen from linear and branched, saturated and unsaturated divalent C1-C22 hydrocarbon radicals, optionally interrupted by at least one hetero atom chosen from N, O, and S, and/or optionally substituted with at least one hydroxyl radical;
- X− is an anion deriving from an acid chosen from mineral and organic acids;
- and
- Y is a polysaccharide residue;
- excluding compounds of formula (I) in which Y represents a polymeric starch structure, A is —CH2—, and R1=R2=R3=—CH3.
A process for cosmetic treatment of a keratinous support chosen from skin, scalp, hair, eyelashes, eyebrows, nails and mucous membranes, comprising applying to said keratinous support a composition comprising, in a cosmetic or dermatological acceptable medium, at least one compound chosen from compounds of formula (I):
- 23
- in which:
- R1, R2, and R3, which may be identical or different, are chosen from linear and branched, saturated and unsaturated C1-C30 hydrocarbon radicals optionally interrupted by at least one hetero atom chosen from N, O, and S and/or optionally substituted with at least one radical selected from —OH, halogen and C6-C22 aryl radicals;
- A is chosen from linear and branched, saturated and unsaturated divalent C1-C22 hydrocarbon radicals, optionally interrupted by at least one hetero atom chosen from N, O, and S, and/or optionally substituted with at least one hydroxyl radical;
- X− is an anion deriving from an acid chosen from mineral and organic acids;
- and
- Y is a polysaccharide residue;
- excluding compounds of formula (I) in which Y represents a polymeric starch structure, A is —CH2—, and R1=R2=R3=—CH3.
Dependencies are inferred from the claim text.