US 12,264,295 B2
Encapsulated pro-perfume compounds
Arnaud Struillou, Satigny (CH); and Estelle Rassat, Satigny (CH)
Assigned to FIRMENICH SA, Satigny (CH)
Appl. No. 17/439,942
Filed by FIRMENICH SA, Satigny (CH)
PCT Filed Mar. 20, 2020, PCT No. PCT/EP2020/057767
§ 371(c)(1), (2) Date Sep. 16, 2021,
PCT Pub. No. WO2020/188079, PCT Pub. Date Sep. 24, 2020.
Claims priority of application No. 19163967 (EP), filed on Mar. 20, 2019.
Prior Publication US 2023/0032098 A1, Feb. 2, 2023
Int. Cl. C11B 9/00 (2006.01); C11D 3/50 (2006.01)
CPC C11B 9/0034 (2013.01) [C11B 9/0019 (2013.01); C11B 9/0061 (2013.01)] 19 Claims
 
1. A fragrance delivery system comprising
a perfume oil, and
a carrier material,
wherein the perfume oil comprises at least one pro-perfume compound, and
wherein the perfume oil is entrapped within a matrix formed by the carrier material,
wherein the fragrance delivery system is a solid fragrance delivery system; and
wherein the pro-perfume compound is a compound of formula

OG Complex Work Unit Chemistry
wherein:
a) w represents an integer from 1 to 10000;
b) n represents 1 or 0;
c) m represents an integer from 1 to 4;
d) P represents a hydrogen atom or a radical susceptible of generating an odoriferous α,β-unsaturated ketone, aldehyde or carboxylic ester and is represented by the formula

OG Complex Work Unit Chemistry
in which the wavy line indicates the location of the bond between said P and X;
R1 represents a hydrogen atom, a C1 to C6 alkoxyl radical or a C1 to C15 linear, cyclic or branched alkyl, alkenyl or alkadienyl radical, optionally substituted by C1 to C4 alkyl groups; and
R2, R3 and R4 represent a hydrogen atom, an aromatic ring or a C1 to C15 linear, cyclic or branched alkyl, alkenyl or alkadienyl radical, optionally substituted by C1 to C4 alkyl groups; or two, or three, of the groups R1 to R4 are bonded together to form a saturated or unsaturated ring having 5 to 20 carbon atoms and including the carbon atom to which said R1, R2, R3 or R4 groups are bonded, this ring being optionally substituted by C1 to C8 linear, branched or cyclic alkyl or alkenyl groups; and with the proviso that at least one of the P groups is of the formula (II) as defined hereinabove;
e) X represents a functional group selected from the group consisting of the formulae i) to xiv):

OG Complex Work Unit Chemistry
in which formulae the wavy lines are as defined previously and the bold lines indicate the location of the bond between said X and G, and R represents a hydrogen atom, a C1 to C22, saturated or unsaturated, alkyl group or an aryl group, optionally substituted by C1 to C6 alkyl or alkoxyl groups or halogen atoms; and with the proviso that X may not exist when P represents a hydrogen atom;
f) G represents a multivalent radical (with a m+1 valence) derived from an aryl radical, optionally substituted, or a divalent cyclic, linear or branched alkyl, alkenyl, alkadienyl or alkylbenzene hydrocarbon radical having from 1 to 22 carbon atoms, or a tri-, tetra- or pentavalent cyclic, linear or branched alkyl, alkenyl, alkadienyl or alkylbenzene hydrocarbon radical having from 1 to 22 carbon atoms, said hydrocarbon radical being optionally substituted and containing from 1 to 10 functional groups selected from the group consisting of ether, ester, ketone, aldehydes, carboxylic acids, thiols, thioethers, amine, quaternary amines and amides; optional substituents of G are halogen atoms, N02, OR6, NR62, COOR6 or R6 groups, R6 representing a C1 to C15 alkyl or alkenyl group; and
g) Q represents a hydrogen atom (in which case w=1 and n=1), or represents a group [[P—X]m[G]n] wherein P, X, G, n and m are as defined previously (in which case w=1), or a dendrimer selected from the group consisting of the polyalkylimine dendrimers, amino acids (e.g. lysine) dendrimers, mixed amino/ether dendrimers and mixed amino/amide dendrimers, or a polysaccharide selected from the group consisting of cellulose, cyclodextrines and starches, or a cationic quaternised silicon polymer or still a polymeric backbone derived from a monomeric unit selected from the group consisting of the formulae A) to E) and mixtures thereof:

OG Complex Work Unit Chemistry
in which formulae the hatched lines indicate the location of the bond between said monomeric unit and G;
z represents an integer from 1 to 5;
n is defined as previously;
R7 represents, simultaneously or independently, a hydrogen atom, a C1-C15 alkyl or alkenyl group, a C4-C20 polyalkyleneglycol group or an aromatic group;
R8 represents, simultaneously or independently, a hydrogen or oxygen atom, a C1-C5 alkyl or glycol or does not exist; and
Z represents a functional group selected from the group consisting of the formulae 1) to 8), the branching units of the formulae 9) to 11), and mixtures thereof:

OG Complex Work Unit Chemistry
in which formulae the hatched lines are defined as previously, the dotted arrows indicate the location of the bond between said Z and the remaining part of the monomeric unit and the arrows indicate the location of the bond between said Z and either G or the remaining part of the monomeric unit, R7 being as defined previously; and with the proviso that Z does not represent a group of formula 1), 3), and 7) if the monomeric unit is of formula B).