Treatment Compositions Having Modified Amino Acid Multimers

Abstract

The present disclosure relates to treatment compositions comprising modified amino acid multimer compounds that may be useful for delivering specific benefit agents, such as perfume raw materials or antimicrobial agents. The present disclosure also relates to methods of making and using such compounds and compositions. The present disclosure also relates to related precursor compounds and premix compositions.

Description

[Technical field]

[0001] The present disclosure relates to treatment compositions comprising modified amino acid multimer compounds that may be useful for delivering specific benefit agents, such as perfume raw materials or antimicrobial agents. The present disclosure also relates to methods of making and using such compounds and compositions. The present disclosure also relates to related precursor compounds and premix compositions. [Background technology]

[0002] Many treatment compositions, such as those suitable for treating fabrics, contain various benefit agents, such as perfumes, that provide benefits in the end use of the product.Many of these benefit agents are intended to be deposited on target surfaces, such as fabrics.Therefore, it is useful and desirable to increase the deposition efficiency of such benefit agents, as well as their release profile.

[0003] The deposition of such benefit agents can be advantageously promoted by deposition aids and / or carrier materials, but several factors are involved in the selection of suitable materials. For example, the selected materials must provide an improved deposition profile compared to the benefit agents they are intended to deliver, which is particularly challenging in aqueous processing environments such as the wash and / or rinse cycles of an automatic washing machine. For sustainability reasons, it may be desirable for such materials to be naturally derived and / or biodegradable. In addition, it may be desirable for such materials to have a suitable loading efficiency of the delivered benefit agent, as well as an appropriate release rate of the deposited benefit agent. Furthermore, it may be desirable for such materials to be able to interact with a range of different benefit agents and / or be able to be conveniently incorporated into product formulations in a variety of ways. Summary of the Invention [Problem to be solved by the invention]

[0004] Thus, there is a need for improved components in treatment compositions that can efficiently deposit on target surfaces and release benefit agents, especially when used in aqueous environments, and more preferably, such components are derived (at least in part) from materials of natural origin. [Means for solving the problem]

[0005] The present disclosure relates to treatment compositions that include treatment aids and modified amino acid multimeric compounds that may be useful for delivering specific benefit agents.

[0006] For example, the disclosure relates to a treatment composition comprising a processing aid and a modified amino acid multimeric compound, the multimeric compound comprising a central linking group and 2-6 amino acid moieties each covalently bonded to the central linking group by a heteroatom selected from the group consisting of O, S, and N, preferably O, the central linking group comprising 3-18 carbon atoms, each amino acid moiety comprising a carbon backbone comprising one or more carbon atoms, a carbonyl group comprising a carbon atom, and a nitrogen atom, the heteroatoms being bonded directly to a carbon atom of the carbonyl group and to the central linking group, at least one amino acid moiety comprising an organic moiety covalently bonded to a nitrogen atom of the amino acid moiety, the organic moiety comprising a benefit agent residue, the benefit agent being released upon cleavage of one or more bonds connecting the benefit agent residue to the amino acid moieties, the benefit agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof.

[0007] The present disclosure also relates to a treatment composition comprising a processing adjunct and a modified amino acid multimeric compound, the multimeric compound comprising a central linking group and 2-6 amino acid moieties each covalently bonded to the central linking group, the central linking group comprising 3-18 carbon atoms, each amino acid moiety comprising a carbonyl group at its C-terminus, the carbonyl group comprising a carbon atom, the carbonyl carbon atom being bonded to a heteroatom of the central linking group, the heteroatom being selected from the group consisting of O, S or N, each amino acid moiety further comprising a nitrogen atom at its N-terminus, at least one amino acid moiety comprising a benefit agent residue bonded to the nitrogen atom at the N-terminus of the at least one amino acid moiety, the benefit agent being released upon cleavage of one or more bonds connecting the benefit agent residue to the amino acid moieties, the benefit agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof.

[0008] The present disclosure also provides a processing composition comprising a processing aid and a modified amino acid multimer compound, the modified amino acid multimer compound having Formula I: L[E] t Formula I wherein t is independently an integer from 2 to 6, preferably from 2 to 5, more preferably from 2 to 4, more preferably from 2 to 3, more preferably 2; L is a central linking group that is polyvalent and contains from 3 to 18 carbon atoms; and each E group is independently selected from -GH, -GX, or a moiety according to formula II;

[0009] [ka] provided that the multimeric compound includes at least two E groups that are moieties according to formula II; * represents the point of attachment of the E group to L, the value of x is 1 to 9, preferably 1 to 6, more preferably 1 to 3, even more preferably 1 to 2, and even more preferably 1; each G is independently -O-, -N(R 3 )-, or -S-, preferably each G group is the same and each R 3is, if present, independently selected from H or a monovalent moiety having a molecular weight of 14 to 881 Da, preferably 41 to 255 Da, where X, if present, is a suitable charge-balancing counterion, and each R 1 are independently selected from H or a monovalent moiety having a molecular weight of 15 to 507 Da, preferably R 1 is selected from the side groups of proteinogenic amino acids or monovalent moieties having a molecular weight between 15 and 142 Da, and each R 2 are independently selected from H and a monovalent moiety having a molecular weight of 15 to 1000 Da, preferably 15 to 507 Da, more preferably 15 to 142 Da, and preferably R 2 is H, each A group is a monovalent nitrogen-containing moiety, and at least one A group comprises an independently selected benefit agent residue linked to the remainder of the A group by one or more bonds, the benefit agent being released upon cleavage of the one or more bonds, the benefit agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof.

[0010] The present disclosure also relates to the modified amino acid multimeric compounds described herein.

[0011] The present disclosure also relates to modified amino acid multimer precursor compounds having a structure according to formula I': L[E] t Formula I', wherein L, E, and t are defined above, with the proviso that the multimeric precursor compound comprises at least two E groups which are moieties according to formula II defined above, with the further proviso that each A group of the moiety according to formula II is HN-, or (c) HG'(J) d N(H)-, and G', J, and d are defined as above.

[0012] The present disclosure also relates to a premix composition comprising a modified amino acid multimer precursor compound, a benefit agent, and optionally water, wherein the benefit agent comprises an aldehyde moiety, a ketone moiety, or a combination thereof, and the premix composition optionally further comprises a non-aqueous solvent, more preferably a hydroxyl-containing solvent, even more preferably ethanol.

[0013] The present disclosure also relates to a method of making a treatment composition as described herein, comprising at least one of the following steps: (a) combining a modified amino acid multimer compound with an auxiliary component, preferably the auxiliary component is part of a base composition; (b) combining a premix composition as described in claim 28 with an auxiliary component, preferably the auxiliary component is part of the base composition; (c) combining a modified amino acid multimer precursor compound, a benefit agent, and an auxiliary component, preferably the auxiliary component is part of the base composition, and the modified amino acid multimer compound and the benefit agent are each added as separate inputs to the base composition.

[0014] The present disclosure also relates to a method of treating an article or surface, comprising treating the article or surface with a treatment composition according to the present disclosure, optionally in the presence of water, and optionally further comprising a rinsing and / or drying step. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] The present disclosure relates to treatment compositions comprising modified amino acid multimer compounds that enhance the deposition and release of benefit agents. The amino acid multimer compounds of the present disclosure can therefore be considered "pro-benefit agent compounds" such as pro-perfume compounds.

[0016] The modified amino acid multimeric compounds of the present disclosure (as used herein, "multimeric compounds" or more simply "multimers") comprise at least two amino acid moieties covalently bonded to one another, for example, by a central linking group. The central linking group is preferably relatively hydrophobic, which can help improve the deposition profile of the compound onto a target surface, particularly in aqueous processing environments and / or onto hydrophobic surfaces.

[0017] Additionally, the multimeric compounds of the present disclosure preferably contain one or more residues of benefit agents that are released over time when the multimeric compounds are deposited on a target surface, such as a fabric. The benefit agents that form the residues include aldehyde or ketone moieties that react with the amine groups of the amino acid moieties. When the bond is broken, the benefit agent is released.

[0018] The disclosed multimeric compounds provide more options for modification and loading efficiency compared to single amino acids.For example, a single multimeric compound can conveniently have at least two residues of beneficial agents through the use of a single central linking group.Without being bound by theory, it is believed that through the selection of central linking group and / or side groups of amino acid moiety (e.g., for hydrophobicity), manufacturers can "tune" the multimer accordingly to obtain the desired performance profile depending on the formulation and intended use of the prescription composition.

[0019] The compounds, compositions and related processes of the disclosure are described in more detail below.

[0020] As used herein, the articles "a" and "an" when used in a claim are understood to mean one or more of what is claimed or described. As used herein, the terms "include", "includes" and "including" are meant to be open-ended. The compositions of the present disclosure may comprise, consist essentially of, or consist of the components of the present disclosure.

[0021] The terms "substantially free of" or "substantially free from" may be used herein. This means that the indicated material is in minimal amounts and has not been intentionally added to the composition to form part of the composition, or preferably is not present at analytically detectable levels. It means that the indicated material is present only as an impurity in one of the other intentionally included materials. The indicated material may be present, if at all, at a level of less than 1% by weight of the composition, or less than 0.1% by weight, or less than 0.01% by weight, or even 0% by weight.

[0022] As used herein, the phrase "fabric care composition" includes compositions and formulations designed to treat fabric.Such compositions include, but are not limited to, laundry cleaning compositions and detergents, fabric softening compositions, fabric enhancing compositions, fabric deodorizing compositions, laundry pre-cleaning agents, laundry pre-treatment agents, laundry additives, spray products, dry cleaning agents or compositions, laundry rinse additives, cleaning additives, post-rinse fabric treatment agents, ironing aids, unit dose formulations, delayed delivery formulations, detergents contained on or in porous substrates or nonwoven sheets, and other suitable forms that may be obvious to those skilled in the art in light of the teachings herein.Such compositions can be used as laundry pre-treatment agents, laundry post-treatment agents, or can be added during the rinse or wash cycle of laundry operations.

[0023] As used herein, the phrase "chain atoms" means the sum of all atoms in a designated group or moiety, excluding hydrogen atoms. The chain atoms may be in a straight, branched, and / or cyclic arrangement.

[0024] As used herein, "peptide bond" refers to a bond between the C-terminus of one amino acid (or derivative thereof) and the N-terminus of another amino acid (or derivative thereof). As used herein, the phrase "free of peptide bonds" is not intended to exclude the presence of a typical amide bond other than when the amino acids (or derivatives thereof) are in the C-terminus / N-terminus orientation described. Multimers of the present disclosure are typically not intended to include dipeptides, as such materials tend to have reduced loading capacity for benefit agent residues. The reduced loading capacity is generally due to one less nitrogen available for loading of benefit agent, in which the N-terminus nitrogen of one amino acid is typically bonded to the carbonyl carbon of the C-terminus of another amino acid.

[0025] As used herein, an amino acid "multimer" (modified or not) refers to a compound having more than one amino acid moiety as described herein. Typically, such a material contains 2-6 amino acid moieties. For clarity, a "multimer" as used herein may have only two amino acid moieties. However, a multimer of the present disclosure is not to be understood as being a dimer, trimer, or polypeptide due to differences in configuration.

[0026] Unless otherwise noted, all component or composition concentrations are in terms of the active portion of that component or composition and are exclusive of impurities, e.g., residual solvents or by-products, that may be present in commercial sources of such component or composition.

[0027] All temperatures herein are in degrees Celsius (° C.) unless otherwise indicated. All measurements herein are made at 20° C. and atmospheric pressure unless otherwise stated.

[0028] In all embodiments of the present disclosure, all percentages are by weight of the total composition unless otherwise specified. All ratios are by weight unless otherwise specified.

[0029] It should be understood that every maximum numerical limitation given throughout this specification includes every lower numerical limitation, as if such lower numerical limitation were expressly written herein. Every minimum numerical limit given throughout this specification includes every higher numerical limitation, as if such higher numerical limitations were expressly written herein. Every numerical range given throughout this specification includes every narrower numerical range that falls within such broader numerical range, as if such narrower numerical ranges were all expressly written herein.

[0030] Treatment Composition The present disclosure relates to processing compositions. Processing compositions typically include processing aids and modified amino acid multimeric compounds, each of which is discussed in more detail below.

[0031] The treatment composition may be a consumer product composition. The consumer product composition of the present disclosure may be useful in baby care, beauty care, fabric care, home care, family care, feminine care, and / or health care applications. The treatment composition may be useful for treating surfaces such as fabric, hair, or skin. The consumer product composition may be intended to be used or consumed in the manner in which it is sold. The consumer product composition may not be intended for subsequent commercial manufacture or modification.

[0032] The treatment composition may be a fabric care composition. The treatment composition may be a fabric care composition, a hard surface cleaner composition, a dish care composition, a hair care composition (such as a shampoo or conditioner), a body cleansing composition, or a mixture thereof, preferably a fabric care composition.

[0033] The treatment composition may be a fabric care composition such as a laundry detergent composition (including heavy duty liquid detergents or unit use articles), a fabric conditioning composition (including liquid fabric softening compositions and / or fabric strengthening compositions), a laundry additive, a fabric pretreatment composition (including sprays, pourable liquids, or sprays), a fabric refresher composition (including sprays), or mixtures thereof.

[0034] The treatment composition may be a beauty care composition, such as a hair treatment product (including shampoos and / or conditioners), a skin care product (including creams, lotions, or other topically applied products for consumer use), a shaving care product (including shaving lotions, foams, or pre- or post-shave treatments), a personal cleansing product (including liquid body washes, liquid hand soaps, and / or bar soaps), a deodorant and / or antiperspirant, or mixtures thereof.

[0035] The treatment composition may be a home care composition such as air care, car care, dishwashing, hard surface cleaning and / or treatment, and other cleaning, consumer or institutional.

[0036] The treatment composition may be in the form of a liquid composition, a granular composition, a hydrocolloid, a single compartment pouch, a multi-compartment pouch, a dissolvable sheet, pastilles or beads, a fibrous article, a tablet, a stick, a bar, a flake, a foam / mousse, a nonwoven sheet, or mixtures thereof.

[0037] The treatment composition may be in the form of a liquid. The liquid composition may comprise from about 30% by weight, or from about 40% by weight, or from about 50% by weight, to about 99% by weight, or to about 95% by weight, or to about 90% by weight, or to about 75% by weight, or to about 70% by weight, or to about 60% by weight of the composition. The liquid composition may be a liquid laundry detergent, a liquid fabric conditioner, a liquid dish detergent, a hair shampoo, a hair conditioner, or a mixture thereof.

[0038] The treatment composition may be in the form of a solid. The solid composition may be a powder or granular composition. Such compositions may be agglomerated or spray dried. Such compositions may include a plurality of granules or particles, at least some of which include such granules or particles comprising different compositions. The composition may be a powder or granular cleaning composition, which may include a bleaching agent. The composition may be in the form of beads or pastilles, which may be pastilles from a liquid melt. The composition may be an extruded product.

[0039] The treatment composition may be in particulate form, such as a plurality of microparticles. An individual microparticle may have a mass of about 1 mg to about 1 g. The emulsion may be dispersed in a water-soluble carrier. The water-soluble carrier may be selected from the group consisting of polyethylene glycol, sodium acetate, sodium bicarbonate, sodium chloride, sodium silicate, polypropylene glycol polyoxoalkylene, polyethylene glycol fatty acid ester, polyethylene glycol ether, sodium sulfate, starch, and mixtures thereof. The water-soluble carrier may be a water-soluble polymer. When the treatment composition is in granular form, it may comprise about 25% to about 99.99% by weight of the water-soluble carrier and about 0.001% to about 50% by weight of the multimeric compound according to the present disclosure. The particulate form may be in the form of beads or pastilles.

[0040] The treatment composition may be in the form of a unit dose article, such as a tablet, pouch, sheet, or fibrous article. Such pouches typically include a water-soluble film, such as a polyvinyl alcohol water-soluble film, that at least partially encapsulates the composition. Suitable films are available from MonoSol, LLC (Indiana, USA). The composition may be encapsulated in a single compartment pouch or a multi-compartment pouch. A multi-compartment pouch may have at least two, at least three, or at least four compartments. A multi-compartment pouch may include compartments arranged side-by-side and / or stacked. The composition contained in the pouch or its compartments may be liquid, solid (such as a powder), or a combination thereof. The pouch composition may have a relatively low amount of water, such as less than about 20% by weight of the detergent composition, or less than about 15% by weight, or less than about 12% by weight, or less than about 10% by weight, or less than about 8% by weight.

[0041] The treatment composition may be in the form of a spray, for example, dispensed via an aerosol container having a trigger sprayer and / or a valve.

[0042] The treatment composition is applied for 20 seconds. -1 and 21°C, 1 to 1500 centipoise (1 to 1500 mPa * s), 100-1000 centipoise (100-1000mPa * s), or 200-500 centipoise (200-500mPa * s).

[0043] Modified Amino Acid Multimer Compounds The present disclosure relates to modified amino acid multimeric compounds that typically include 2-6 amino acid moieties covalently bonded to a central linking group. Such compounds typically do not include peptide bonds, although amide bonds may be present in some cases. The multimeric compounds include at least one benefit agent residue, preferably at least two benefit agent residues. The multimeric compounds can be deposited on a target surface, thereby bringing the benefit agent residue to the target surface. When the bond holding the residues is cleaved, the benefit agent is released. The release of the benefit agent may be triggered by any suitable mechanism, such as the presence of water or heat, preferably water, especially when the linking bond is an imine bond. The bond may be cleaved under ambient conditions over time. The released benefit agent typically includes an oxygen-containing moiety, i.e., an aldehyde moiety or a ketone moiety. As further described herein, the central linking group may include one or more hydrophobic moieties that can promote improved deposition and / or performance efficiency.

[0044] Such multimeric compounds may be part of a treatment composition as described herein. The treatment composition may comprise from about 0.001% to about 30%, preferably from about 0.001% to about 20%, more preferably from about 0.001% to about 15%, 0.001% to about 10%, preferably from about 0.01% to about 5% of the modified amino acid multimeric compound, based on the weight of the treatment composition. The treatment composition may comprise a sufficient amount of the modified amino acid multimeric compound to deliver from about 0.01% to about 10%, preferably from about 0.1% to about 5%, of the benefit agent released by the multimeric compound, based on the weight of the treatment composition.

[0045] The modified amino acid multimeric compounds of the present disclosure comprise a central linking group and 2-6 amino acid moieties covalently bonded to the central linking group by a heteroatom selected from the group consisting of O, S, and N, preferably O, wherein the central linking group comprises 3-18 carbon atoms, the central linking group may be a divalent, trivalent, tetravalent, pentavalent, or hexavalent organic moiety, each amino acid moiety comprises a carbon backbone comprising one or more carbon atoms, a carbonyl group comprising a carbon atom, and a nitrogen atom, the heteroatoms are bonded directly to a carbon atom of the carbonyl group and to the central linking group, at least one amino acid moiety comprises an organic moiety covalently bonded to a nitrogen atom of the amino acid moiety, the organic moiety comprises a benefit agent residue, and the benefit agent is released upon cleavage of one or more bonds connecting the benefit agent residue to the amino acid moieties, and the benefit agent comprises an aldehyde moiety, a ketone moiety, or a combination thereof.

[0046] The modified amino acid multimeric compound may comprise a central linking group and 2-6 amino acid moieties covalently attached to the central linking group, typically by non-peptide covalent bonds, wherein the central linking group comprises 3-18 carbon atoms, the central linking group may be a divalent, trivalent, tetravalent, pentavalent, or hexavalent organic moiety, each amino acid moiety comprises a carbonyl group at its C-terminus, the carbonyl group comprises a carbon atom, the carbonyl carbon atom is bonded to a heteroatom of the central linking group, the heteroatom being selected from the group consisting of O, S, or N, each amino acid moiety further comprises a nitrogen atom at its N-terminus, at least one amino acid moiety comprises a benefit agent residue bonded to the nitrogen atom at the N-terminus of at least one amino acid moiety, the benefit agent is released upon cleavage of one or more bonds connecting the benefit agent residue to the amino acid moiety, the benefit agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof. For clarity, the C-terminus of each amino acid moiety is proximal to the central linking group and the N-terminus is distal to the central linking group.

[0047] As described above, the modified amino acid multimer multimeric compound comprises at least two amino acid moieties covalently linked to a central linking group. The multimeric compound comprising each amino acid moiety is typically derived from an amino acid. Proteinogenic amino acids may be the preferred starting material since they tend to occur naturally, making such compounds attractive for environmental or sustainability reasons. For most naturally occurring amino acids, the stereogenic carbon alpha to the amino group has an L-configuration. D-amino acids are occasionally found in nature. Either L-amino acids or D-amino acids, as well as mixtures, may be used, although economic factors may favor the more abundant L-amino acids. In this context, biosynthetic amino acids may be preferred.

[0048] Each amino acid moiety may comprise a carbon backbone. The carbon backbone may be part of a carbon-containing core, which may also comprise one or more side groups, nitrogen atoms, and carbonyl groups. It is understood that the carbon backbone does not include the carbon of the carbonyl-containing moiety or side group (if present). The carbon backbone of each amino acid moiety may each independently comprise 1-9 carbon atoms, preferably 1-6 carbon atoms, preferably 1-3 carbon atoms, more preferably 1-2 carbon atoms, and even more preferably 1 carbon atom. For reasons of mass efficiency, a relatively small number of carbon atoms may be preferred. In particular, a backbone comprising only one carbon atom may be preferred, as such a structure is indicative of a naturally occurring proteinogenic amino acid.

[0049] The carbon-containing core may be derived from amino acids. Preferably, the core is derived from proteinogenic amino acids. In particular, naturally occurring or biosynthetic amino acids may be preferred. Such materials may be preferred for environmental / sustainability reasons and because they tend to be readily available at reasonable cost.

[0050] At least one side group of the parent amino acid from which the amino acid moiety is derived may be selected from hydrogen or a suitable organic group, preferably hydrogen or an organic group having from 1 to about 18 atoms, preferably carbon atoms. The at least one side group may comprise one or more functional groups, such as a carboxyl group, an amine group, a thiol group, or a hydroxyl group. The at least one side group may be linear or branched. The at least one side group may comprise an aryl ring. The amino acid may preferably comprise only one non-hydrogen side group (e.g. only one organic group). The amino acid may comprise two or more non-hydrogen side groups. The at least one side group preferably comprises a side group of a proteinogenic amino acid. The carbon-containing core may comprise at least one side group that is hydrogen and at least one side group that is an organic group. For example, if the amino acid moiety is based on or derived from glycine, all side groups may be hydrogen.

[0051] At least one, preferably at least two, more preferably all of the amino acid moieties are independently derived from a proteinogenic amino acid, preferably a proteinogenic amino acid selected from cysteine, glycine, aspartic acid, glutamic acid, lysine, or a combination thereof, more preferably cysteine. The amino acids may be selected for advantageous reactivity and / or deposition profiles.

[0052] At least two, and preferably all, of the amino acid moieties may be derived from amino acids having the same identity, and preferably from proteinogenic amino acids having the same identity. For example, the amino acid moieties may be derived from cysteine. Forming multimers from amino acids of the same identity may facilitate convenient and / or predictable reactions (e.g., the amino acid moieties are substantially identical).

[0053] One way in which the multimeric compounds of the present disclosure are "modified" amino acid multimers is that the amino acid moieties are attached to a central linking group at the C-terminal portion of each of the amino acid moieties (e.g., the end bearing a carbonyl group).

[0054] For example, as noted above, each amino acid moiety contains a carbonyl group, which typically is / was part of the carboxyl group of the parent amino acid. The carbonyl group contains a carbon atom that is double-bonded to an oxygen atom (C=O). Typically, the carbon atom of the carbonyl group is directly bonded to a heteroatom selected from O, S, or N.

[0055] The heteroatom is typically part of the central linking group. The heteroatom of the central linking group may be attached to the carbon atom of the amino acid moiety via any suitable reaction. For example, the (parent) amino acid of one or more of the amino acid moieties may be linked to the central linking group by (a) reacting the carboxylic acid group of the amino acid with an alcohol of the organic group via an esterification reaction, (b) reacting with an amine of the organic group via an amidation reaction, or (c) reacting with a thiol group of the organic group via a thioesterification reaction. Such reactions may result in ester, amide, or thioester linking groups, respectively. Such linking groups, each of which is a type of carbonyl-containing moiety group, may be preferred over others for ease of reaction. Compounds formed with such carbonyl-containing moieties may be more preferred for environmental reasons, since these types of groups may degrade (e.g., hydrolyze) over time and / or in the presence of water, leaving the material to revert to, for example, a common amino acid.

[0056] In the portion of the central linker where a heteroatom is not attached to an amino acid moiety, the heteroatom may be capped with a hydrogen.

[0057] The central linking group may contain 3 to 18 carbon atoms, or 3 to 16 carbon atoms, preferably 5 to 12 carbon atoms, and more preferably 8 to 12 carbon atoms. Without wishing to be bound by theory, it is believed that a certain minimum number of carbon atoms may be useful for increasing the relative hydrophobicity of the linking group, and thus the resulting compound may aid in facilitating increased deposition or performance. Preferably, the central linking group further contains an oxygen atom, for example, in an orientation such that a mixture of carbon and oxygen atoms forms at least one alkoxylate group, preferably at least one ethoxylate group, at least one propoxylate group, or mixtures thereof.

[0058] The modified amino acid multimeric compound may comprise a polymeric component of three or more repeating units, for example, where the repeating units are alkoxylate groups, preferably ethoxylate groups, propoxylate groups, or mixtures thereof. The central linking group may preferably comprise a polymeric component.

[0059] The central linking group may be a divalent, trivalent, tetravalent, pentavalent, or hexavalent organic moiety. The valency typically corresponds to the number of heteroatoms in the central linking group available to react with the amino acid moieties. The central linking group is preferably a divalent, trivalent, or tetravalent organic moiety, more preferably a divalent moiety. To balance the loading efficiency of the amino acid moieties (and any benefit agent residues thereon) with the bulkiness of the resulting compound, a somewhat lower valency of the central linking group may be preferred.

[0060] The central linking group can be derived from any suitable organic moiety, preferably one that contains multiple heteroatoms. Suitable starting materials for preparing the modified amino acid multimeric compounds of the present disclosure preferably contain sufficient heteroatoms selected from O, S, and N, preferably O and N, most preferably O, to allow the formation of up to tE groups, where t and E are described in more detail below. Suitable starting materials have the following structure: L[GH] t wherein each G is independently selected from O, S, NH, and NR 3and R is a heteroatom or heteroatom-containing moiety selected from 3 is a monovalent moiety having a molecular weight of 14 to 881 Da, preferably 41 to 255 Da, and L is as described below.

[0061] A variety of simple starting materials can be used to prepare the central linking group of the modified amino acid multimeric compound of the present disclosure. For example, the central linking group can be derived from polyhydric alcohols, polyamines, polythiols, and compounds with a mixture of alcohol, thiol, and amine groups, provided that the starting materials comply with the carbon and heteroatom number restrictions described above. Heteroatoms or heteroatom-containing moieties in such starting materials can be acylated under conditions well known in the art to arrive at the modified amino acid multimeric compound of the present invention. Any of the materials listed below that are not specifically described as being either racemic, optically pure, or optically enriched can be in such a state and can serve as suitable starting materials. As described in more detail below, the letter "G" is used herein to describe the heteroatom to which the amino acid moiety can be linked.

[0062] The central linking group can be derived from a polyhydric alcohol having two -OH moieties. Suitable polyhydric alcohols having two -OH moieties (each G is O) include 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, 1,2-ethanediol, 1,2-propanediol, 1,3-butanediol, 1,5-pentanediol, 1,3-propanediol, 1,7-heptanediol, 1,9-nonanediol, 1,11-undecanediol, 2,3-butanediol, 2,4 -Pentanediol, 2,5-Hexanediol, 1,4-Butanediol, 1,4-Pentanediol, 1,5-Hexanediol, 1,9-Decanediol, 1,7-Octanediol, 1,6-Heptanediol, 1,10-Undecanediol, 1,8-Nonanediol, 2,7-Octanediol, 2,6-Heptanediol, 1,11-Dodecanediol, 2,9-Decanediol, 2,11-Dodecanediol, 2,8-Nonanediol, 2,10-Udecanediol, 1,12-Tridecanediol, 2,12-Tridecanediol, 2,13-Tetradecanediol, Tricyclo[3.3.1.13,7]decane-1,3-diol, 1,2-Benzenediol, 1,2-Propanediol, 3-(2-Methoxyphenoxy)-, 1,1-Cyclopropanedimethanol, 1,3-Propanediol, 2-Phenyl-, 1,2-Benzenedimethanol, Tricyclo[3.3.1.13,7]decane-1-methano , 3-hydroxy-, 1,2-propanediol, 3-(phenylmethoxy)-, 1,3-propanediol, 2,2-dimethyl-, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, 1,2-propanediol, 3-methoxy-, 1,2-ethanediol, 1-phenyl-, 1,3-cyclopentanediol, 1,3-propanediol, 2-(phenylmethoxy)-, [1,1'-bicyclohexyl]-4,4'-diol, 1.5-Butanol, 3-Methyl-, Hexitol, 2,5-Anhydro-3,4-Dideoxy-, Cyclohexanol, 4,4'-(1-Methylethylidene)bis-, 1,2-Cyclohexanediol, 1,3-Cyclohexanediol, Cyclohexanemethanol, 4-Hydroxy-, 1,3-Propanediol, 2-Butyl-2-Ethyl-, 1,3-Propanediol, 2-Methyl-2-Propyl-, 1,3-Propanediol, 2-Propyl-, Bicyclo[2.2.2]octane-1,4- Dimethanol, 1,3-dioxolane-2,2-diethanol, 1,2-propanediol, 3-[(2-ethylhexyl)oxy]-, 1,3-propanediol, 2-ethyl-2-methyl-, 1,2-propanediol, 3-phenoxy-, 1,3-propanediol, 2-pentyl-, 1,3-pentadecanone, 2,2,4-trimethyl-, 1,3-propanediol, 2-methyl-, tricyclo[3.3.1.13,7]decane-1,3-dimethanol, 1,3-cyclopentanedione, 2-Ethyl-1,2-propanediol, 3,3-diethoxy-, 1,3-propanediol, 2-Ethyl-, 1,2-propanediol, 3-(2-propen-1-yloxy)-, 1,1-cyclopentane dimethanol, [1,1'-biphenyl]-2,2'-dimethanol, 1,3-propanediol, 2-Butyl-, 1,2-propanediol, 3-ethoxy-, 1,2-cyclopentanediol, 1H-indene-1,2-diol, 2,3-dihydro-, 1,3-propanediol , 2,2-dibutyl-, 1,2-benzenediol, 3,6-dimethyl-, 1,5-pentanediol, 3,3-dimethyl-, 1,2-benzenediol, 4-octyl-, 1,2-ethanediol, 1,2-diphenyl-, 1,5-pentanediol, 2,4-diethyl-, 1,2-propanediol, 3-(dodecyloxy)-, 1,3-propanediol, 2-(1-methylethyl)-, 1,2-propanediol, 3-propoxy-, cyclohexanemethanol, 2-hydroxy-, 1.Diols include, but are not limited to, 4-butanol, 2-methyl-, 1,2-propanediol, 3-(hexyloxy)-, 1,4-butanediol, 2,2-dimethyl-, 7-octene-1,2-diol, 1,3-pentanediol, 2-methyl-, 1,5-pentanediol, 2-methyl-, 2,4-pentanediol, 3-methyl-, 1,2-propanediol, 3-(nonyloxy)-, 1,3-cyclohexanedimethanol, 1,3-butanol, 2-methyl-, cyclopentaneethanol, 2-hydroxy-, tricyclo[3.3.1.13,7]decane-2,4-diol, and 1,5-hexanediol, 2-ethyl-. Preferred diol materials include 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, and 1,12-dodecanediol-.

[0063] The central linking group can be derived from a polyhydric alcohol having three -OH moieties. Suitable polyhydric alcohols having three -OH moieties (each G is O) include 1,2,3-propanetriol (also known as glycerol), 1,2,6-hexanetriol, 1,2,4-butanetriol, 1,2,5-pentanetriol, 1,2,10-decanetriol, 1,2,8-octanetriol, 1,2,7-heptanetriol, 1,2,9-nonanetriol, 1,3,5-pentanetriol, 1,4,7-heptanetriol, 1,3,6-hexanetriol, 1,3,8-octanetriol, 1, 2,11-Undecanetriol, 1,5,9-Nonanetriol, 1,4,8-Octanetriol, 1,3,10-Decanetriol, 1,4,9-Nonanetriol, 1,4,12-Dodecanetriol, 1,3-Propanediol, 2-Ethyl-2-(hydroxymethyl)-, 1,3-Propanediol, 2-(hydroxymethyl)-2-methyl-, 1,3-Propanediol, 2-(hydroxymethyl)-, 1,3-Propanediol, 2-(hydroxymethyl)-, 1,3-Propanediol, 2-(hydroxymethyl)-2-[(2-propen-1-yloxy)methyl]-, 1 ,3-Propanediol,2-(hydroxymethyl)-2-(methoxymethyl)-,2,4-Pentanediol,3-Ethyl-3-(1-hydroxyethyl)-,1,3-Propanediol,2-(hydroxymethyl)-2-propyl-,2,4-Pentanediol,3-(hydroxymethyl)-,1,3-Butanediol,2-(hydroxymethyl)-3-methyl-,1,3-Pentanediol,2-(hydroxymethyl)-2-methyl-,1,3-Propanediol,1-(dimethylamino)-2-(hydroxymethyl)-,1 ,3-Propanediol,2-(hydroxymethyl)-2-(phenylmethyl)-, 1,3-Propanediol,2-(hydroxymethyl)-2-(phenoxymethyl)-, 1,3-Propanediol,2-(hydroxymethyl)-2-[(2-methylphenoxy)methyl]-, 1,3-Propanediol,2-(hydroxymethyl)-2-[(2-methoxyphenoxy)methyl]-, xylopyranoside, methyl 3-deoxy-3-(hydroxymethyl)-, β-D-, bicyclo[2.2.1]heptane-2,6,7-triol, 1,3-Butanediol, 2-(hydroxymethyl)-, 1,3-Propanediol, 2-Hexyl-2-(hydroxymethyl)-, 1,3-, Propanediol, 2-(hydroxymethyl)-2-(3-methylbutyl)-, 1,3-Propanediol, 2-(3-buten-1-yl)-2-(hydroxymethyl)-, 1,3-Propanediol, 2-(hydroxymethyl)-2-[(phenylmethoxy)methyl]-, 1,3-Propanediol, 2-(hydroxymethyl)-2-[(3-methylphenoxy)methyl]-, 1,3-Butanediol, 2 -(hydroxymethyl)-2-methyl-, 1,3-butanediol, 2-ethyl-2-(hydroxymethyl)-, 1,3-pentanediol, 2-(hydroxymethyl)-4-methyl-, 1,3-propanediol, 2-(hydroxymethyl)-2-(2-methylpropyl)-, butanenitrile, 4-hydroxy-3,3-bis(hydroxymethyl)-, 1,3-propanediol, 2-(hydroxymethyl)-2-[(methoxymethoxy)methyl]-, 1,1-cyclohexanedimethanol, 2-hydroxy-3-methyl-, 1,3-cyclopentane Tandiol, 2-(hydroxymethyl)-2-methyl-, (1S,3S-), 1,3-propanediol, 2-butyl-2-(hydroxymethyl)-, 1,3-propanediol, 2-(hydroxymethyl)-2-pentyl-, 2,4-pentanediol, 3-ethyl-3-(hydroxymethyl)-, 1,3-propanediol, 2-(ethoxymethyl)-2-(hydroxymethyl)-, 1,3-butanediol, 2-(hydroxymethyl)-2,3-dimethyl-, 1,3-butanediol, 2-(hydroxymethyl)-4-methoxy-2-methyl -, 1,3-propanediol, 2-(hydroxymethyl)-2-octyl-, 1,3-propanediol, 2-(hydroxymethyl)-2-(2-propen-1-yl)-, 1,3-propanediol, 2-(butoxymethyl)-2-(hydroxymethyl)-, 1,3-propanediol, 2-(propoxymethyl)-2-(hydroxymethyl)-, 4-pentene-1,3-diol, 2-(hydroxymethyl)-2-methyl-, butanenitrile, 2,4-dihydroxy-3-(hydroxymethyl)-3-methyl-, 1,3-propanediol,2-(hydroxymethyl)-2-[(2-methylbutoxy)methyl]-, pentanenitrile, 3,5-dihydroxy-4-(hydroxymethyl)-4-methyl-, 1,3-propanediol, 2-(hydroxymethyl)-1-phenyl-, 1,3-propanediol, 1-cyclopropyl-2-(hydroxymethyl)-2-methyl-, 1,3-propanediol, 2-(1-hydroxycyclopropyl)-2-methyl-, 1,3-propanediol, 1-cyclobutyl-2-(hydroxymethyl)-2-methyl-, 1,3-cyclopentanediol, 2-(hydroxymethyl)-, 1,3-cyclopentanediol, 2-(hydroxymethyl)-2-methyl-, 1,3-cyclohexanediol, 2-(hydroxidized) Examples of triols include, but are not limited to, 1,2,3-cyclopentanediol, 2-(hydroxymethyl)-2-methyl-, 1,1-cyclopentanedimethanol, 2-hydroxy-4-methoxy-, 1,3-cyclopentanediol, 2-(hydroxymethyl)-2-(2-propen-1-yl)-, 1,3-hexanediol, 2-(hydroxymethyl)-4-methyl-, 1,3-butanediol, 2-(hydroxymethyl)-2-propyl-, 1,3-butanediol, 2-ethyl-2-(hydroxymethyl)-3-methyl-, 1,3-pentanediol, 2-(hydroxymethyl)-2,4-dimethyl-, 1,3-pentanediol, 2-(hydroxymethyl)-4,4-dimethyl-, and 3,5-heptanediol, 4-(1-hydroxypropyl)-. A preferred triol material is 1,2,3-propanetriol (also known as glycerol).

[0064] The central linking group can be derived from a polyhydric alcohol having four -OH moieties. Suitable polyhydric alcohols having four -OH moieties (each G is O) include 1,2,3,4-butanetetrol, 1,2,7,8-octanetetrol, hexitol, 3,4-dideoxy-, hexitol, 2,5-dideoxy-, 1,2,9,10-decanetetrol, 1,2,6,7-heptanetetrol, L-threo-hexitol, 3,4-dideoxy-, D-threo-hexitol, 2,5-dideoxy-, 1,2,11,12-dodecanetetrol, D-erythro-pentitol, 2-deoxy-, pentitol, ...3,4-butanetetrol, 1,2,3,4-butanetetrol, 1,2,3,4-butanetetrol, 1,2,3,4-butanetetrol, 1,2,3,4-butanetetrol, 1,2,3,4-butanetetrol, 1,2,3,4-butanetetrol, 1,2,3,4-butanetetrol, 3-deoxy-, erythro-pentitol, 2-deoxy-, pentitol, 2-deoxy-, D-threo-pentitol, 2-deoxy-, 1,4,5,8-octane tetrol, hexitol, 2,3-dideoxy-, threo-hexitol, 3,4-dideoxy-, D-erythro-hexitol, 2,3-dideoxy-, threo-hexitol, 2,5-dideoxy-, L-threo-pentitol, 3-deoxy-, L-threo-pentitol, 2-deoxy-, ribitol, 3-deoxy-, D-, 1,2,8,9- Nonanetetrol, 1,3,6,8-octanetetrol, D-threo-hexitol, 3,4-dideoxy-, 1,2,5,7-heptanetetrol, erythro-pentitol, 3-deoxy-, D-threo-pentitol, 3-deoxy-, threo-pentitol, 3-deoxy-, 1,2,4,5-pentanetetrol, 1,3-propanediol, 2,2-bis(hydroxymethyl)-, 1,2,3-propanetriol, 2-(hydroxymethyl)-, 1,3-propanediol, 2-(hydroxymethyl)-2-[[ [5-(hydroxymethyl)-1,3-dioxane-5-yl]methoxy]methyl]-, 1,2,4-cyclopentanetriol, 3-(hydroxymethyl)-5-methoxy-, 1,3-propanediol, 2-[(hydroxymethoxy)methyl]-2-(hydroxymethyl)-, 1,3-butanediol, 2,2-bis(hydroxymethyl)-, 1,2,3-butanetriol, 2-(hydroxymethyl)-, 1,3-propanediol, 2-(hydroxymethyl)-2-(mercaptomethyl)-, 1,4-butanediol, 2,including, but not limited to, 2-bis(hydroxymethyl)-, 1,2,4-butanetriol, 3-(hydroxymethyl)-3-methyl-, 1,3-propanediol, 2-[[3-(1,1-dimethylethoxy)-2-hydroxypropoxy]methyl]-2-(hydroxymethyl)-, 1,1-cyclohexanedimethanol, 2,4-dihydroxy-, 1,2,4-cyclopentanetriol, 3-(hydroxymethyl)-, 1,1,3-cyclohexanetrimethanol, 2-hydroxy-3-methyl-, 1,2-cyclobutanedimethanol, 1,3-dihydroxy-, 3aH-indene-1,2,3a,7-tetrol, octahydro-, 1,1,3-propanetriol, 2-(hydroxymethyl)-, and 3-propanediol, and 2-[(2-hydroxyethoxy)methyl]-2-(hydroxymethyl)-. A preferred material having four OH groups is pentaerythritol.

[0065] The central linking group can be derived from a polyhydric alcohol having five -OH moieties. Suitable polyhydric alcohols having five -OH moieties (where each G is O) include xylitol, ribitol, D-arabinitol, L-arabinitol, arabinitol, pentitol, D-arabino-hexitol, 5-deoxy-, hexitol, 3-deoxy-, D-arabino-hexitol, 2-deoxy-, D-ribo-hexitol, 2-deoxy-, D-xylo-hexitol, 5-deoxy-, arabino-hexitol, 3-deoxy-, xylo-hexitol, 3-deoxy-, ribo ... , 1,3,4,5,7-heptane pentol, 1,2,5,8,9-nonane pentol, hexitol, 2-deoxy-, L-arabino-hexitol, 2-deoxy-, D-xylo-hexitol, 2-deoxy-, L-arabino-hexitol, 5-deoxy-, D-erythro-hexitol, 3-deoxy-, (2ξ)-, 1,2,3,5,7-heptane pentol, 1,1,3,3-cyclohexane tetramethanol, 2-hydroxy-, 2H-pyran-3,3,5,5(4H,6H)-tetramethanol, 4-hydro oxy-, 1,2-propanediol, 3-[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]-, β-D-erythro-2-pentulofuranose, 3-C-(hydroxymethyl)-, 1,2,3,4-butanetetrol, 2-(hydroxymethyl)-, D-ribofuranose, 2-C-(hydroxymethyl)-, bicyclo[2.2.1]heptane-2,3,5,6,7-pentol, 1,1,3,3-cyclopentanetetramethanol, 2-hydroxy-, 1,1,3,3-cyclohexanetetramethanol, 2-hydrox- Examples of hydroxymethyl-5-methyl-, β-D-ribopyranose, 2-C-(hydroxymethyl)-, β-D-liquipyranosyl,2-C-(hydroxymethyl)-, β-D-ribopyranose, 3-C-(hydroxymethyl)-, α-L-lyxopyranose, 3-C-(hydroxymethyl)-, β-D-xylopyranose, 3-C-(hydroxymethyl)-, 5-cyclohexene-1,2,3,4-tetrol, 2-(hydroxymethyl)-, and 2-pentulofuranose, 3-C-(hydroxymethyl)-.

[0066] The central linking group can be derived from a polyhydric alcohol having six -OH moieties. Suitable polyhydric alcohols having six -OH moieties (where each G is O) include D-mannitol, D-glucitol, galactitol, L-glucitol, L-iditol, L-mannitol, allitol, D-iditol, L-altritol, D-altritol, mannitol; hexitol, D-galactitol, iditol, glucitol, altritol, 1,2,3,5,6,7-heptanehexitol, 1,3-propanediol, 2,2'-[oxybis(methylene)]bis[2-(hydroxymethyl)-, 1,3-propanediol, , 2,2'-[methylenebis(oxymethylene)]bis[2-(hydroxymethyl)-, 1,5-pentanediol, 2,2,4,4-tetrakis(hydroxymethyl)-, pentitol, 3-C-(hydroxymethyl)-, pentitol, 2-C-(hydroxymethyl)-, D-myo-inositol, 3-deoxy-3-(hydroxymethyl)-, L-chiro-inositol, 1-deoxy-1-(hydroxymethyl)-, and 1,2,3,4,5-cyclopentanepentol, 1-(hydroxymethyl)-.

[0067] The central linking group can be derived from materials that contain both alcohol and amino moieties. Suitable starting materials containing a mixture of alcohol and amino-GH groups include, but are not limited to: (a) 4-amino-1-butanol, 6-amino-1-hexanol, 3-amino-1-propanol, 5-amino-1-pentanol, 1-amino-2-butanol, 8-amino-1-octanol, 10-amino-1-decanol, 12-amino-1-dodecanol, 7-amino-1-heptanol, 4-amino-2-butanol, 1-amino-2-pentanol, 11-amino-1-undecanol, 9-amino-1-nonanol, 5-amino-2-pentanol, 1-amino-3-pentanol, 1-amino-3-hexanol, 1-amino-2-hexanol, 1-amino-2-heptanol, one NH2 and one OH moiety, including, but not limited to, 1-amino-3-heptanol, 1-amino-2-decanol, 1-amino-2-octanol, 1-amino-3-octanol, 6-amino-3-hexanol, 1-amino-2-dodecanol, 1-amino-2-nonanol, 6-amino-2-hexanol, 1-amino-2-undecanol, 2-pentanol, 5-amino-, R-, 1-amino-3-dodecanol, 1-amino-3-decanol, 8-amino-2-octanol, 1-amino-3-nonanol, 4-octanol, 8-amino-, 1-propyl-4-heptanol; (b) one NH and two OH moieties, including, but not limited to, 3-amino-1,2-propanediol, 4-amino-1,2-butanediol, 1-amino-2,3-butanediol, 4-amino-1,3-butanediol, 5-amino-1,2-pentanediol, 1-amino-2,3-hexanediol, 6-amino-1,2-hexanediol; (c) one NH2 and three OH moieties, including, but not limited to, 4-amino-1,2,3-butanetriol, 1-amino-1,2-dideoxy-D-erythro-pentitol, and (d) one NH and four OH moieties, including, but not limited to, 1-amino-1-deoxy-D-ribitol, 1-amino-1-deoxy-D-arabinitol, livermin, 1-amino-1-deoxy-D-xylitol, 5-amino-5-deoxy-D-arabinitol, 1-amino-1-deoxy-L-arabinitol; (e) -two NH2 and one OH moiety, including but not limited to pentanol, 1,5-diamino-, butanol, 1,2-diamino-, propanol, 1,3-diamino-.

[0068] The central linking group can be derived from materials that contain both thiol and amino moieties. Suitable starting materials containing a mixture of thiol and amino GH groups include, but are not limited to: (a) 1-butanethiol, 4-amino-, 1-propanethiol, 3-amino-, 2-propanethiol, 1-amino-, 1-pentanethiol, 5-amino-, 1-hexanethiol, 6-amino-, 1-heptanethiol, 7-amino-, 2-pentanethiol, 1-amino-, 1-octanethiol, 8-amino-, 2-hexanethiol, 1-amino-, 1-undecanethiol, 11-amino-, 2-butanethiol, 1-amino-, 1-dodecanthiol one NH2 and one SH moiety, including, but not limited to, 12-amino-, 3-pentanethiol, 1-amino-, 2-pentanethiol, 5-amino-, 2-butanethiol, 4-amino-, 2-undecanethiol, 1-amino-, 2-octanethiol, 1-amino-, 2-nonanethiol, 1-amino-, 2-hexanethiol, 6-amino-, 2-heptanethiol, 1-amino-, 1-decanethiol, 10-amino-; (b) one NH2 and two SH moieties, including, but not limited to, 1,2-propanedithiol, 3-amino-, 1,3-butanedithiol, 4-amino-, 2,3-butanedithiol, 1-amino-, and 1,2-butanedithiol, 4-amino-.

[0069] The central linking group can be derived from a material that contains multiple amino groups. Suitable starting materials containing multiple amino GH groups include, but are not limited to: (a) 1,8-octanediamine, 1,5-pentanediamine, 1,6-hexanediamine, 1,10-decanediamine, 1,4-butanediamine, 1,7-heptanediamine, 1,12-dodecanediamine, 1,3-propanediamine, 1,11-undecanediamine, 1,9-nonanediamine, 1,3-pentanediamine, 1,2-pentanediamine, 1,6-hexanediamine, 2,2,4 (or 2,4,4)-trimethyl-, 1,4-pentanediamine, 1,2-butanediamine, 1,5-hexanediamine, 1,3-butanediamine, 1,6-hexanediamine, C,C,C-trimethyl-, 1,2-nonanediamine, 1,4-heptanediamine , 1,2-heptanediamine, 1,2-decanediamine, 1,4-hexanediamine, 1,3-hexanediamine, 1,2-propanediamine, N-dodecyl-, 1,2-octanediamine, 1,6-octanediamine, 1,7-octanediamine, 1,2-dodecanediamine, 1,4-undecanediamine, 1,6-hexanediamine, bis(2-methylpropyl)-, 1,2-undecanediamine, 1,4-decanediamine, 1,4-octanediamine, 1,4-nonanediamine, 1,5-pentanediamine, methyl-, 1,6-heptanediamine, 1,7-nonanediamine, 1,5-heptanediamine; (b) three NH2 and moieties, including, but not limited to, 1,2,3-propanetriamine, 1,3,5-pentanetriamine, 1,4,7-heptanetriamine, 1,3,6-hexanetriamine, 1,6,11-undecanetriamine, 1,2,4-pentanetriamine, 1,2,4-butanetriamine, 1,2,5-pentanetriamine, 1,2,7-heptanetriamine, 1,2,6-hexanetriamine, 1,3,5-hexanetriamine; (c) 1,2-propanediamine, one NH and one NH moiety, including but not limited to N-octyl-; (d) 2 NH2 moieties and either 0, 1, or 2 NH moieties, including, but not limited to, 1,2-ethanediamine, 1,2-ethanediamine, N1-(2-aminoethyl)-, 1,2-ethanediamine, and N1,N2-bis(2-aminoethyl)-.

[0070] The central linking group may preferably be derived from a polyhydric alcohol, since such starting materials facilitate convenient processing and desirable release profiles. The polyhydric alcohol may preferably be selected from diols, triols, or pentaerythritol, and even more preferably from 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, glycerol; or pentaerythritol.

[0071] For example, it may be preferable to select a central linking group that is characterized by some degree of hydrophobicity to promote deposition efficiency under aqueous processing conditions such as in an automatic washing machine. Stated differently, the central linking group may be an organic moiety that is relatively hydrophobic, especially if the valence of the central linking group is relatively low (e.g., 2). A relatively large number of carbon atoms (e.g., 10 or 12 versus 3 or 4) may contribute to relatively greater hydrophobicity.

[0072] As noted above, the central linking group may be attached to the amino acid moieties by a carbonyl-containing moiety selected from an ester, amide, or thioester moiety. Such a carbonyl-containing moiety may be formed by reacting the carboxylic acid terminus of the core amino acid with a suitable functional group (e.g., an alcohol, amine, or thiol) of a suitable organic group that serves as the central linking group.

[0073] For example, it may be preferred that the carbonyl-containing moiety linking the central linking group to the amino acid moiety is an ester moiety (e.g., the heteroatom is oxygen) because of the lower cost of the alcohol precursor or the favorable environmental profile of the resulting ester.

[0074] The carbonyl-containing moiety linking the central linking group to the amino acid moiety may preferably be an amide moiety (e.g., the heteroatom is nitrogen). Amide moieties may be preferred for stability reasons and / or when the beneficial agent fragment is an antimicrobial fragment. In such cases, the compound may have an additional organic moiety, preferably hydrophobic, attached to the nitrogen atom. Without wishing to be bound by theory, it is believed that the additional hydrophobic moiety, even if relatively small, can contribute a suitable degree of hydrophobicity and associated performance benefits.

[0075] The central linking group may be optionally substituted, but such substitutions are preferably selected to maintain the hydrophobicity of the organic group. For example, the organic group may include relatively hydrophobic substitutions. Additionally or alternatively, the organic group may include hydrophilic substitutions, but these are preferably kept to a minimum and / or the number of chain atoms is appropriately selected to offset some of the hydrophilicity of the substitutions. For clarity, the substitutions discussed in this paragraph are not intended to include heteroatoms of the central linking group that are further attached to an amino acid moiety.

[0076] The central linker may be branched or unbranched. The central linker may contain alkyl branches (including cycloalkyl) and / or aryl branches.

[0077] Preferably, the central linking group is linear / unbranched. Such moieties may be preferred due to their convenient availability, performance profile, and relatively low environmental impact.

[0078] The central linking group may be derived from a mixture of feedstock materials. The feedstock materials may include materials having varying chain lengths. In such cases, the chain lengths described herein for the central linking group are understood to be weight average chain lengths.

[0079] Additionally or alternatively, the feedstock materials used to form the central linking group may include some materials that are linear and some materials that are branched. Thus, when the feedstocks are reacted to form the precursors or multimeric compounds of the present disclosure, some materials will include linear multivalent moieties and other materials will include branched multivalent moieties. Such mixtures are contemplated in the present disclosure.

[0080] Multimeric compounds can contain additional beneficial agent residues, which can be released eventually from modified amino acid multimeric compounds in addition to one or more beneficial agent residues attached to the nitrogen atom of amino acid moiety.Such a configuration can be preferred for the reason of loading efficiency.Such a configuration can also be preferred to allow various beneficial agents to be released from the same compound.

[0081] For example, the additional benefit agent residue may have a different identity than the benefit agent residue attached to the nitrogen of the core. Both residues may be of the same category of benefit agent (e.g., both derived from perfume raw materials), but they may have different identities. Preferably, the first and second benefit agents comprise different functional groups. For example, the first benefit agent may comprise an aldehyde or ketone moiety and the second benefit agent may comprise a functional group that is not an aldehyde or ketone moiety. The second benefit agent may comprise a functional group that is an alcohol, an amine, a thiol, or a combination thereof.

[0082] Preferably, the second benefit agent contains a functional group that is an alcohol group. Such materials may be preferred to provide a broader spectrum of materials released from the multimeric compound (e.g., an aldehyde- or ketone-containing benefit agent in combination with an alcohol-containing benefit agent).

[0083] The central linking group may be substituted with the residue of an additional benefit agent. The side groups of the amino acid moieties may be substituted with the residue of an additional benefit agent.

[0084] The second benefit agent may be a perfume raw material, preferably an alcohol-containing perfume raw material. In such cases, it is preferred that the first benefit agent (e.g., the parent of the residue attached to the nitrogen atom of the amino acid moiety) is also a perfume raw material that allows for a more efficient perfume delivery and / or a more complex olfactory experience.

[0085] For environmental reasons, it may be preferred that the central linking group is derived from a naturally occurring material or feedstock, particularly when the carbon-containing core is derived from a naturally occurring amino acid. Suitable naturally occurring materials or feedstocks may include naturally occurring fats and / or oils.

[0086] The modified amino acid multimeric compounds of the present disclosure include at least two (typically up to six) amino acid moieties covalently linked by a central linking group. The central linking group may be a divalent moiety attached to the carbon atom of the carbonyl group of each amino acid moiety. In particular, the multimers of the present disclosure do not include peptide bonds. Thus, dipeptides, tripeptides, polypeptides, and the like are not within the scope of the present disclosure. Such materials are not preferred because, due to the peptide configuration, the nitrogen atom of each amino acid moiety is not available to carry a beneficial agent residue. Thus, the more common amide type bonds can be present in the multimers of the present disclosure.

[0087] As described above, at least one amino acid moiety includes an organic moiety covalently bonded to a nitrogen atom of the amino acid moiety, the organic moiety including a benefit agent residue. When the bond(s) connecting the residue to the nitrogen atom are cleaved, e.g., by a triggering event, the multimeric compound releases the benefit agent, the benefit agent including an aldehyde moiety, a ketone moiety, or a combination thereof. These benefit agents are described in more detail below.

[0088] One or more, preferably each, of the amino acid moieties may comprise an organic moiety covalently bonded to a nitrogen atom of the respective amino acid moiety. Preferably, the organic moiety attached to each nitrogen atom comprises benefit agent residues linked by bonds that can be cleaved to release the benefit agent. Such an arrangement (e.g., 2-6 benefit agent residues on one multimeric compound) may be preferred for reasons of loading efficiency.

[0089] The modified amino acid multimeric compounds of the present disclosure may be characterized by a structure according to Formula I: L[E] t Formula I. In formula I, the L group represents a central linking group, and at least two (and up to six) of the E groups represent amino acid moieties linked to the central linking group by a heteroatom selected from O, N, or S, preferably O. The multimeric compounds generally do not contain peptide bonds. For clarity, the multimers (including the central linking group) may contain amide bonds, so long as they are not peptide bonds.

[0090] In formula I, the index t is independently an integer from 2 to 6, preferably from 2 to 5, more preferably from 2 to 4, more preferably from 2 to 3, more preferably 2. The index t corresponds approximately to the valence of the central linking group (group L, see below).

[0091] In formula I, L is a central linking group that is multivalent and contains from 3 to 18 carbon atoms.

[0092] In formula I, each E group is independently selected from -GH, -GX (wherein X is a suitable charge-balancing counterion), or a moiety according to formula II:

[0093] [ka] provided that the multimeric compound includes at least two E groups that are moieties according to formula II. The moieties according to formula II correspond substantially to the amino acid moieties described above. * indicates the point of attachment of the E group to L.

[0094] In formula II, the value of x is 1 to 9, preferably 1 to 6, more preferably 1 to 3, even more preferably 1 to 2, and even more preferably 1. When x is 1, the moiety according to formula II (e.g., the amino acid moiety) may be derived from a naturally occurring or biosynthetic proteinogenic amino acid, which may be preferred for environmental reasons.

[0095] In the moiety according to formula II, each G (which ultimately corresponds to a heteroatom as described above) is independently -O-, -N(R 3 Each G group is selected from the group consisting of -S-, -C ... 3 where present, is independently selected from H or a monovalent moiety having a molecular weight of 14 to 881 Da, preferably 41 to 255 Da.

[0096] It may be preferred that G is -O-. When G is -O-, the resulting ester may be preferred for environmental reasons as well as the ready availability of alcohol-based raw materials that can function as the central linking group.

[0097] It is -N(R 3 In such cases, it may be preferable to use a relatively small R 3 Moieties, especially hydrogen, may be preferred when forming amide bonds, for example, due to convenient reaction and availability of feedstock materials. Amides may be formed, for example, from protected or unprotected amino acids. When protected, inorganic and organic acids may be most preferred. For unprotected amino acids, chelate catalysts from group III elements, group IV elements, and transition metal catalysts may be preferred. Catalysts containing elements of B, Si, and Ti are even more preferred.

[0098] When X is present, it is preferably selected from sodium, potassium, lithium or ammonium.

[0099] In the moiety according to formula II, each R 1is independently selected from H or a monovalent moiety having a molecular weight of 15 to 507 Da, P is preferably R 1 is selected from the side groups of proteinogenic amino acids or monovalent moieties having a molecular weight between 15 and 142 Da.

[0100] In the moiety according to formula II, each R 2 are independently selected from H and a monovalent moiety having a molecular weight of 15 to 1000 Da, preferably 15 to 507 Da, more preferably 15 to 142 Da. 2 is H. At least one R 2 comprises a residue of an additional benefit agent, preferably R 2 It may be preferred that R is a monovalent moiety having a molecular weight of 54 to 1000 Da. 2 R may comprise at least one residue of a benefit agent. 2 If R contains at least one residue of a beneficial agent, 2 R is preferably a monovalent moiety having a molecular weight of 54 to 1000 Da. 2 does not contain at least one residue of a benefit agent, R 2 is preferably selected from H and a monovalent moiety having a molecular weight between 15 and 507 Da, preferably R 2 is H or a monovalent moiety having a molecular weight between 15 and 142 Da, more preferably R 2 is H.

[0101] In the moiety according to formula II, each A group is a monovalent nitrogen-containing moiety, and at least one A group comprises an independently selected benefit agent residue linked to the remainder of the A group by one or more bonds, and the benefit agent is released upon cleavage of the one or more bonds. The benefit agent comprises an aldehyde moiety, a ketone moiety, or a combination thereof.

[0102] Each A group is independently selected from the following: (a) HN-; (b) Z ** N-, (in the formula, ** represents the connecting bond between the nitrogen atom and the carbon atom of the Z group), (c) HG'(J) d N(H)-, and (d)

[0103] [ka] wherein at least one A group is independently selected from (b) or (d), more preferably at least one A group is selected from (b) Z ** N-, and even more preferably both A groups are selected from (b) Z ** N-, where each Z group is an independently selected benefit agent residue. The various moieties (e.g., Z, G', J) and indices (e.g., d) are described in more detail below.

[0104] At least one A group is independently selected from the group consisting of (b) Z ** N-, (in the formula, ** represents the connecting bond between the nitrogen atom and the carbon atom of the Z group, the connecting bond being one of: (i) a double bond, thereby forming an imine bond, or (ii) a single bond formed from a 1,4-addition when the benefit agent from which the benefit agent residue is derived contains an α-β unsaturated carbonyl-containing moiety that is an aldehyde or ketone moiety; Z ** The nitrogen atom of the N-group may be selected to be further bonded to a hydrogen (-H).

[0105] In the multimeric compounds according to formula I, at least one A group is selected from the group consisting of b) Z ** N-, Z ** The Z group of the N-moiety is

[0106] [ka] and mixtures thereof, 4 )(R 5 ) and -CH(R 8 CH2C(O)R 5It may be preferred that each moiety represents a residue of a benefit agent. The residue of the benefit agent preferably has a molecular formula that differs from the molecular formula of the benefit agent (e.g., the one from which it is derived and / or the one to which it becomes when released) only by having less than one O atom or more than one H atom. The benefit agent includes an aldehyde moiety, a ketone moiety, or a combination thereof, such moieties react favorably with the nitrogen of the amino acid moiety.

[0107] Preferably the benefit agent is a perfume raw material containing 4 to 34 carbon atoms, preferably R 4 are independently selected from monovalent organic moieties, where R 5 and R 8 are independently selected from the group consisting of hydrogen and monovalent organic moieties, with the proviso that R 4 and R 5 or R 8 and R 5 may be linked to form a cyclic divalent organic moiety. 5 and R 8 are not both hydrogen in the same Z group. Suitable benefit agents are described in more detail below.

[0108] ** When represents a double bond (eg, an imine bond), the Z group may be a benefit agent residue having the structure:

[0109] [ka] In such a case, R 4 may be selected from monovalent organic moieties, R 5 may be selected from the group consisting of hydrogen and monovalent organic moieties, with the proviso that R 4 and R 5 may be linked to form a cyclic divalent moiety. When the Z group is the residue of an aldehyde-containing benefit agent, R 5 is hydrogen. When the Z group is the residue of a ketone-containing benefit agent, R 5 is an organic moiety. Such residues have the formula R 4 -C(O)-R 5The benefit agents and their residues may be characterized by a relatively low molecular weight, for example, from about 100 g / mol to about 1000 g / mol, preferably from about 100 g / mol to about 500 g / mol. 4 and R 5 The groups can be selected accordingly.

[0110] ** When the connecting bond is a single bond, the Z group may be represented by the following structure:

[0111] [ka] ** represents the attachment point of the linking bond to the nitrogen atom (which in this case also includes the hydrogen moiety attached to the nitrogen by a single bond), and R 5 and 8 is selected from the group consisting of hydrogen and monovalent organic moieties. In such cases, the Z group may be derived from an α-β unsaturated carbonyl (e.g., an aldehyde or ketone). When the Z group is the residue of an aldehyde-containing benefit agent, R 5 is hydrogen. When the Z group is the residue of a ketone-containing benefit agent, R 5 is an organic moiety. Preferably, R 5 and R 8 are not both hydrogen in the same Z group. Such residues have the formula R 8 -CH=CH-C(O)-R 5 may be derived from and / or result in the release of a benefit agent according to

[0112] At least one A group is independently selected from the group consisting of: (c) HG'(J) d N(H)-, or (d

[0113] [ka] where the index d is selected from 1 to 3, preferably d is 2 to 3, and more preferably d is 2. wherein each G' is independently -O-, -S-, or -N(R 7 )-, preferably G' is -O-, the Z group contains 4 to 34 carbon atoms, N and G' are bonded to the same carbon atom of the Z group, and each R 7 R1, when present, is independently selected from -H or a monovalent moiety having a molecular weight of about 15 to about 255 Da, preferably R 7 is a monovalent moiety having a molecular weight of about 15 to about 142 Da, more preferably a monovalent moiety having a molecular weight of about 15 to about 30 Da, where each J is independently C(R 9 )2-O-, and -N(R 9 ), and preferably each J is selected from the group consisting of C(R 9 )2, and each R 9 are independently selected from H or a monovalent moiety having a molecular weight of 14 to 990 Da, more preferably R 9 is selected from H or a monovalent moiety having a molecular weight between 14 and 186 Da, and even more preferably R 9 is H, with the proviso that the first R 9 and the second R 9 Where possible, they may be combined as a divalent substituent, preferably the divalent substituent is a fused ring, a spirocyclic ring, or =N(R 7 ), ═O, and ═S; 7 is as defined above, if present.

[0114] It may be preferred that at least one of the following is true, with potential benefits of the arrangement provided in parentheses: for a given compound, two or more A groups contain benefit agent residues (efficient loading); for a given compound, the identities of the A groups are the same (convenient processing); for a given compound, the identities of the A groups are different (allowing for flexible and / or tunable processing); for a given compound, the identities of the Z groups are the same (convenient loading and / or efficient delivery of a particular benefit agent), and / or for a given compound, the identities of the Z groups are different (allowing for convenient delivery of multiple benefit agents, more complex performance benefits). One or more of these statements may be true, unless contradictory.

[0115] Benefit agents and their residues The modified amino acid multimeric compounds of the present disclosure include benefit agent residues derived from aldehyde-containing benefit agents, ketone-containing benefit agents, or combinations thereof. The benefit agent residues may be derived from benefit agents that include an aldehyde moiety. The benefit agent residues may be derived from benefit agents that include a ketone moiety. The benefit agent may include an alpha-beta unsaturated carbonyl group that is an aldehyde or ketone moiety.

[0116] As used herein, the benefit agent from which the benefit agent residue is derived may be referred to as the parent benefit agent.

[0117] The aldehyde or ketone moiety of the parent benefit agent may react with the nitrogen atom of the amino acid moiety (e.g., at the N-terminus) to result in the benefit agent fragment attached to the core at the nitrogen atom. As mentioned above, this may be through a linking bond that may be a double bond, which is an imine bond, or a single bond formed via a 1,4-addition process, such as a 1,4-Michael-type addition. When the linking bond connecting the benefit agent fragment to the nitrogen atom is formed via a 1,4-addition, the parent benefit agent may include an alpha-beta unsaturated carbonyl, where the carbonyl is an aldehyde or ketone moiety.

[0118] When the linking bonds are broken, for example by hydrolysis, the benefit agent is released. The linking bonds can be broken by triggering conditions, such as the presence of water or elevated temperature. When the treatment composition is used to treat fabrics, such triggering conditions can occur during wear, storage, or normal use, such as wiping or toweling a wet surface. The linking bonds can also be broken under ambient degradation, for example over time.

[0119] The benefit agent residue may be derived from any suitable benefit agent, which may include a perfume raw material, an antimicrobial agent, an insecticide, an insect repellent, an antifungal agent, a herbicide, a hueing dye, an antioxidant, a non-perfume organoleptic agent, or a combination thereof, preferably a perfume raw material, an antimicrobial agent, or a combination thereof, more preferably a perfume raw material. Some of these benefit agents are described in more detail below.

[0120] A.Fragrance raw materials The benefit agent may be a perfume raw material ("PRM") that includes an aldehyde moiety, a ketone moiety, or a mixture thereof. The benefit agent residue (e.g., Z group) may be derived from the perfume raw material.

[0121] As used herein, the term "perfume raw material (or "PRM")" refers to a compound that may have a molecular weight of at least about 100 g / mol (optionally up to about 1000 g / mol, preferably up to about 500 g / mol) and is useful for imparting odors, fragrances, essences or scents, either alone or together with other perfume raw materials. Lists of common PRMs can be found in various reference sources, such as, for example, "Perfume and Flavor Chemicals" Volumes I and II; Steffen Arctander Allured Pub. Co. (1994) and "Perfumes: Art, Science and Technology", Miller, PM and Lamparsky, D., Blackie Academic and Professional (1994).

[0122] Perfume raw materials containing an aldehyde moiety are provided below in Table B. The materials provided in Table B are believed to be illustrative (but non-limiting) examples of PRMs suitable for use according to the present disclosure.

[0123] [Table 1-1]

[0124] [Table 1-2]

[0125] The perfume raw materials from which the benefit agent residue is formed may be selected from the group consisting of aldehyde-containing PRMs in Table B above. The PRM from which the PRM residue is formed may comprise an aldehyde moiety and is preferably selected from the group consisting of methylnonylacetaldehyde, benzaldehyde, floralozone, isocyclocitral, tripral (ligustral), presylchemone B, lilial, decylaldehyde, undecylenic aldehyde, cyclamen homoaldehyde, cyclamen aldehyde, dupical, oncidal, adoxal, melonal, calypsone, anisaldehyde, heliotropin, cuminaldehyde, scentenal, 3,6-dimethylcyclohexyl aldehyde, ... The cinnamaldehyde may be selected from the group consisting of dihex-3-ene-1-carbaldehyde, satinaldehyde, canthoxal, vanillin, ethyl vanillin, cinnamaldehyde, cis-4-decenal, trans-4-decenal, cis-7-decenal, undecylenic aldehyde, trans-2-hexenal, trans-2-octenal, 2-undecenal, 2,4-dodecadienal, cis-4-heptenal, Florydral, butylcinnamaldehyde, limoneral, amylcinnamaldehyde, hexylcinnamaldehyde, citronellal, citral, cis-3-hexen-1-al, and mixtures thereof.

[0126] As mentioned above, the polymeric compound may include residues of perfume raw materials that include a ketone moiety. Perfume raw materials that include a ketone moiety are provided in Table C below. The materials presented in the table are believed to be illustrative (but non-limiting) examples of PRMs suitable for use in accordance with the present disclosure.

[0127] [Table 2-1]

[0128] [Table 2-2]

[0129] The perfume raw materials from which the benefit agent residue is formed may be selected from the group consisting of ketone-containing PRMs in Table C above. The PRM from which the PRM residue is formed may contain a ketone moiety and may preferably be selected from the group consisting of nerolion, 4-(4-methoxyphenyl)butan-2-one, 1-naphthalen-2-ylethanone, nectaryl, trimofix O, fleuramone, delta-damascone, beta-damascone, alpha-damascone, methyl ionone, 2-hexylcyclopent-2-en-1-one, galbascone, and mixtures thereof.

[0130] The benefit agent residue is a perfume raw material, preferably methylnonyl, acetaldehyde, benzaldehyde, floralozone, isocyclocitral, triplral (ligustral), presylchemone B, lilial, decyl aldehyde, undecylenic aldehyde, cyclamen homoaldehyde, cyclamen aldehyde, dupical, oncidal, adoxal, cyclohexyl aldehyde ... adoxal, melonal, calypsone, anisaldehyde, heliotropin, cuminaldehyde, scentenal, 3,6-dimethylcyclohex-3-ene-1-carbaldehyde, satinaldehyde, canthoxal, vanillin, ethyl vanillin, cinnamaldehyde, cis-4-decenal, trans-4 -Decenal, cis-7-decenal, undecylenic aldehyde, trans-2-hexenal, trans-2-octenal, 2-undecenal, 2,4-dodecadienal, cis-4-heptenal, Florydral, butylcinnamaldehyde, limonellal, amylcinnamaldehyde, hexylcinnamaldehyde, citronellal, citral, cis-3-hexene The benefit agent may be derived from a perfume raw material that may be selected from the group consisting of: 1-naphthalene-2-ylethanone, nectaryl, trimofix O, fleuramone, delta-damascone, beta-damascone, alpha-damascone, methyl ionone, 2-hexylcyclopent-2-en-1-one, galbascone, and mixtures thereof. Since mixtures of PRMs are more likely to provide a pleasant odor experience, the materials, preferably those from Tables B and C, may be present as mixtures.

[0131] The perfume raw materials herein, including those listed above, are available from a variety of suppliers, including International Flavors and Fragrances of New York, NY USA, Givaudan of Vernier Switzerland, Firmenich of Geneva, Switzerland, Symrise of Holzminden, Germany, Kao of Tokyo, Japan, Takasago of Tokyo, Japan, and Florasynth of Tel-Aviv, Israel.

[0132] B. Antibacterial Agents The benefit agent may be an antimicrobial agent that includes an aldehyde moiety, a ketone moiety, or a mixture thereof. Antimicrobial agents suitable for use in the multimeric compounds of the present invention may include acetylacetone enolate, gossypol, nootkatone, or a mixture thereof.

[0133] Methods for making modified amino acid multimer compounds and related precursor compounds The modified amino acid multimeric compounds according to the present disclosure can be made by reacting a multimeric precursor compound with a benefit agent. Thus, the present disclosure relates to a process for producing the modified amino acid multimeric compounds.

[0134] A modified amino acid multimeric precursor compound (or "multimeric precursor compound" or simply "precursor compound" as used herein) may comprise at least two amino acid moieties covalently attached to a central linking group.

[0135] For example, a modified amino acid multimer precursor compound of the disclosure may comprise a central linking group and 2-6 amino acid moieties each covalently bonded to the central linking group by a (distinct) heteroatom selected from the group consisting of O, S, and N, preferably O, wherein the central linking group comprises 3-18 carbon atoms, and each amino acid moiety comprises a carbon backbone comprising one or more carbon atoms, a carbonyl group comprising a carbon atom, and a nitrogen atom, and the heteroatoms are bonded directly to the carbon atom of the carbonyl group and to the central linking group.

[0136] The precursor compound does not (yet) contain a residue of a beneficial agent attached to any nitrogen atom of the amino acid moiety. In fact, the precursor compound may be a modified amino acid multimeric compound prior to reaction with a beneficial agent, in which the nitrogen atom is in the form of a primary amine (-NH2) or HG' (J). d It is in the N(H) form. The core, side groups, carbonyl-containing moieties, and hydrophobic moieties are preferably as described above.

[0137] The modified amino acid multimer precursor compound may have a structure according to formula I': L[E] t Formula I', wherein L, E, and t are as defined above, with the proviso that the multimeric precursor compound comprises at least two E groups that are moieties according to formula II as defined above, with the further proviso that each A group of the moiety according to formula II is (a) HN-, or (c) HG'(J). d N(H)-, and G', J, and d are as defined above. The preferences provided above for the remaining groups or indices other than A apply equally to formula I'.

[0138] The polyvalent central linking group has the following formula L[GH] t Compounds according to the formula (I) can be modified at the amino acid moiety by reacting them with the carboxyl groups of two or more amino acids via, for example, esterification, amidation, or thioesterification reactions.

[0139] Accordingly, the present disclosure provides a method of making a modified amino acid multimer precursor compound, the method comprising the steps of providing a multivalent central linking group and reacting the central linking group, preferably via a heteroatom, with two or more (preferably up to six) amino acids, preferably at the carboxylic acid / C-terminus.

[0140] The modified amino acid multimer precursor compound can be obtained by the steps of: (i) providing a molar equivalent of an amino acid moiety that includes a carboxylic acid terminus; (ii) providing one molar equivalent of L[GH] t (iii) providing an amino acid moiety and L[GH] to form a mixture;t (iv) combining the mixture with a slight molar excess of an acid (preferably sulfuric acid, methanesulfonic acid, or para-toluenesulfonic acid, or a mixture thereof) in a suitable reaction vessel; (v) heating the combined mixture at 100° C. to 150° C. for 1 hour to 36 hours; (v) adjusting the pH to at least about 7; and (vi) separating at least a portion of the salt formed during neutralization from the product.

[0141] The multimeric precursor compounds (and / or multimeric precursor compositions made according to the methods provided herein) can be reacted with a benefit agent to form the modified amino acid multimeric compounds described herein.

[0142] Supplementary ingredients The treatment compositions of the present disclosure, which may be consumer products, may include auxiliary materials that may provide a benefit in the intended end use of the composition or may be processing and / or stabilizing aids.

[0143] Suitable adjunct materials may include surfactants, conditioning actives, deposition aids, rheology modifiers or structurants, antioxidants, bleaching systems, stabilizers, builders, chelating agents, dye transfer inhibitors, dispersants, enzymes and enzyme stabilizers, catalytic metal complexes, polymeric dispersants, clay and soil removal / anti-redeposition agents, brighteners, suds suppressors, silicones, hueing agents, aesthetic dyes, neat fragrances, fragrance delivery systems (such as core / shell capsules, other pro-fragrance materials, etc.), structural elastomers, carriers, hydrotropes, processing aids, anti-agglomerating agents, coatings, formaldehyde scavengers, and / or pigments.

[0144] Depending on the intended form, formulation, and / or end use, the compositions of the present disclosure may or may not contain one or more of the following adjunct materials: surfactants, conditioning actives, deposition aids, rheology modifiers or structurants, antioxidants, bleach activators, surfactants, builders, chelating agents, dye transfer inhibitors, dispersants, enzymes and enzyme stabilizers, catalytic metal complexes, polymeric dispersants, clays and soil removal / anti-redeposition agents, brighteners, suds suppressors, dyes, additional fragrances and fragrance delivery systems, structural elastomers, fabric softeners, carriers, hydrotropes, processing aids, structurants, anti-agglomerating agents, coatings, formaldehyde scavengers, and / or pigments.

[0145] The exact nature of these additional components and the concentration of incorporation thereof depend on the physical form of the composition and the nature of the work to be used.However, when one or more adjuvants are present, such one or more adjuvants can be present as detailed below.The following is a non-limiting list of suitable additional adjuvants.

[0146] A. Surfactants The treatment composition of the present disclosure may include a surfactant. The surfactant may be useful, for example, to provide cleaning benefits. The composition may include a surfactant system, which may contain one or more surfactants.

[0147] Treatment compositions of the present disclosure may comprise from about 0.1% to about 70%, or from about 2% to about 60%, or from about 5% to about 50% of a surfactant system by weight of the composition. Liquid compositions may comprise from about 5% to about 40% of a surfactant system by weight of the composition. Compositions suitable for dense formulations, e.g., dense, liquid, gel, and / or unit dose forms, may comprise from about 25% to about 70%, or from about 30% to about 50% of a surfactant system by weight of the composition.

[0148] The surfactant system may include anionic surfactants, nonionic surfactants, zwitterionic surfactants, cationic surfactants, amphoteric surfactants, or combinations thereof. The surfactant system may include nonionic surfactants such as linear alkyl benzene sulfonates, alkyl ethoxylated sulfates, alkyl sulfates, ethoxylated alcohols, amine oxides, or mixtures thereof. The surfactants may be derived, at least in part, from natural sources, such as natural feedstock alcohols.

[0149] Suitable anionic surfactants may include any conventional anionic surfactant. This may include, for example, sulfate detergent surfactants for alkoxylated and / or non-alkoxylated alkyl sulfate materials, and / or sulfonic acid detergent surfactants, such as alkyl benzene sulfonates. The anionic surfactant may be linear, branched, or a combination thereof. Preferred surfactants include linear alkyl benzene sulfonate (LAS), alkyl ethoxylated sulfate (AES), alkyl sulfate (AS), or mixtures thereof. Other suitable anionic surfactants include branched modified alkyl benzene sulfonate (MLAS), methyl ester sulfonate (MES), sodium lauryl sulfate (SLS), sodium lauryl ether sulfate (SLES), and / or alkyl ethoxylated carboxylate (AEC). The anionic surfactant may be present in acid form, salt form, or mixtures thereof. The anionic surfactants may be partially or totally neutralized, for example, with an alkali metal (eg, sodium) or an amine (eg, monoethanolamine).

[0150] The surfactant system may include a nonionic surfactant. Suitable nonionic surfactants include alkoxylated fatty alcohols, such as ethoxylated fatty alcohols. Other suitable nonionic surfactants include alkoxylated alkylphenols, alkylphenol condensates, mid-chain branched alcohols, mid-chain branched alkyl alkoxylates, alkyl polysaccharides (e.g., alkyl polyglycosides), polyhydroxy fatty acid amides, ether-capped poly(oxyalkylated) alcohol surfactants, and mixtures thereof. The alkoxylate units may be ethyleneoxy units, propyleneoxy units, or mixtures thereof. The nonionic surfactants may be linear, branched (e.g., mid-chain branched), or combinations thereof. Particular nonionic surfactants may include alcohols having an average of about 12 to about 16 carbons and an average of about 3 to about 9 ethoxy groups, such as C12-C14 EO7 nonionic surfactants.

[0151] Suitable zwitterionic surfactants include betaines, C8-C9 alkyl dimethyl betaines, including alkyl dimethyl betaines and cocodimethylamidopropyl betaines. 18 (For example, C 12 ~C 18 ) amine oxides (e.g., C 12 ~ 14 dimethylamine oxide), and / or N-alkyl-N,N-dimethylamino-1-propanesulfonate (wherein the alkyl group is C8 to C 18 Or C 10 ~C 14 The zwitterionic surfactant may include any conventional zwitterionic surfactant, such as sulfo and hydroxybetaines, such as (which may be

[0152] Depending on the formulation and / or intended end use, the composition may be substantially free of certain surfactants. For example, a liquid fabric enhancing composition, such as a fabric softener, may be substantially free of anionic surfactants, since such surfactants may negatively interact with cationic components.

[0153] B. Conditioning Actives The treatment compositions of the present disclosure may include conditioning actives. Compositions containing conditioning actives may provide benefits related to softness, anti-wrinkle, anti-static, conditioning, anti-stretch, color, and / or appearance.

[0154] The conditioning active may be present at a level of about 1% to about 99% by weight of the composition. The composition may comprise from about 1%, or from about 2%, or from about 3%, to about 99%, or to about 75%, or to about 50%, or to about 40%, or to about 35%, or to about 30%, or to about 25%, or to about 20%, or to about 15%, or to about 10% by weight of the composition. The composition may comprise from about 5% to about 30% conditioning active by weight of the composition.

[0155] Suitable conditioning actives for the compositions of the present disclosure may include quaternary ammonium ester compounds, silicones, non-ester quaternary ammonium compounds, amines, fatty acid esters, sucrose esters, silicones, dispersible polyolefins, polysaccharides, fatty acids, softening or conditioning oils, polymer latexes, polyhydroxystearic acid and / or its derivatives, glyceride copolymers, or combinations thereof.Preferably, the conditioning active is a cationic conditioning active that can improve the delivery / deposition of multimeric compounds.

[0156] The treatment composition may include a conditioning active, the conditioning active comprising a quaternary ammonium ester compound. Preferably, the quaternary ammonium ester compound is present at a concentration of about 2% to about 35% by weight of the treatment composition, preferably about 4% to about 25% by weight, more preferably about 5% to about 20% by weight, even more preferably about 6% to about 15% by weight, even more preferably about 7% to about 12% by weight. The quaternary ammonium ester compound (also known as an "ester quaternary ammonium") may be a monoester quaternary ammonium, a diester quaternary ammonium, a triester quaternary ammonium, or a combination thereof. Preferably, the diester quaternary ammonium material forms a major portion (whether majority or plurality) of the ester quaternary ammonium compounds. In addition to providing conditioning benefits, it is believed that the deposition and / or performance of the multimeric compounds described in the present disclosure can be improved by selecting the appropriate type and / or concentration of conditioning active (i.e., quaternary ammonium ester compound).

[0157] The quaternary ammonium ester compound may include a compound according to the formula: {R 2 (4-m) -N+-[XYR 1 ] m}A - During the ceremony, m is 1, 2, or 3, with the proviso that in a given molecule, each value of m is the same; Each R may contain from 13 to 22 carbon atoms. 1 are independently linear or branched hydrocarbyl groups, preferably R 1 is linear, and more preferably, R 1 is a partially unsaturated linear alkyl chain, Each R 2 are independently a C1-C3 alkyl group or a hydroxyalkyl group, and / or each R 2is selected from methyl, ethyl, propyl, hydroxyethyl, 2-hydroxypropyl, 1-methyl-2-hydroxyethyl, poly(C2-C3 alkoxy), polyethoxy, benzyl, more preferably methyl or hydroxyethyl; each X is independently -(CH2)n-, -CH2-CH(CH3)-, or -CH(CH3)-CH2-, where each n is independently 1, 2, 3, or 4, preferably each n is 2; each Y is independently -O-(O)C- or -C(O)-O-; A- is independently selected from the group consisting of chloride, bromide, methyl sulfate, ethyl sulfate, sulfuric acid, and nitric acid, preferably A- is selected from the group consisting of chloride and methyl sulfate, more preferably A- is methyl sulfate.

[0158] For monoester quaternary ammonium, m is 1. For diester quaternary ammonium, m is 2. For triester quaternary ammonium, m is 3. The conditioning active may include a mixture of monoester quaternary ammonium and diester quaternary ammonium, or even a mixture of monoester quaternary ammonium, diester quaternary ammonium, and triester quaternary ammonium. As will be appreciated by those skilled in the art, the mixture may depend in part on the starting / feedstock material, such as a dialkanolamine or trialkanolamine.

[0159] The quaternary ammonium ester compound may be derived from a fatty acid characterized by an iodine value of 0 to 140, or 0 to about 90, or about 10 to about 70, or about 15 to about 50, or about 18 to about 30. The iodine value may be determined according to the method provided in U.S. Patent Application Publication No. 2020 / 0407665 (corresponding to WO 2020 / 264566).

[0160] The composition may contain a quaternary ammonium ester compound, a silicone, or a combination of a plurality of pairs thereof, preferably a combination of a plurality of pairs thereof. The total amount of the quaternary ammonium ester compound and the silicone may be about 5% by weight to about 70% by weight, or about 6% by weight to about 50% by weight, or about 7% by weight to about 40% by weight, or about 10% by weight to about 30% by weight, or about 15% by weight to about 25% by weight of the composition. The composition may contain the quaternary ammonium ester compound and the silicone in a weight ratio of about 1:10 to about 10:1, or about 1:5 to about 5:1, or about 1:3 to about 1:3, or about 1:2 to about 2:1, or about 1:1.5 to about 1.5:1, or about 1:1.

[0161] The composition may contain a mixture of different types of conditioning actives. The composition of the present disclosure may contain a particular conditioning active but may be substantially free of other conditioning actives. For example, the composition may be free of quaternary ammonium ester compounds, silicones, or both. The composition may include quaternary ammonium ester compounds but may be substantially free of silicones. The composition may include silicones but may be substantially free of quaternary ammonium ester compounds.

[0162] The conditioning active may include a glyceride copolymer. The glyceride copolymer may be derived from a natural oil. Examples of natural oils include, but are not limited to, vegetable oils, algae oils, fish oils, animal fats, tall oil, derivatives of these oils, any combination of these oils, and the like. Representative non-limiting examples of vegetable oils include low erucic acid rapeseed oil (canola oil), high erucic acid rapeseed oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soybean oil, sunflower oil, linseed oil, palm kernel oil, tung oil, jatropha oil, mustard oil, pennycress oil, camelina oil, hemp seed oil, and castor oil, preferably canola oil. Representative non-limiting examples of animal fats include lard, tallow, poultry oil, yellow grease, and fish oil. Tall oil is a by-product of wood pulp manufacturing. The glyceride copolymer may be a metallated unsaturated polyol ester.

[0163] C. Adhesion aid The treatment composition of the present disclosure may include a deposition aid. The deposition aid may promote deposition of various benefit agents, including the multimeric compounds of the present disclosure, conditioning actives, perfumes or perfume delivery systems (such as encapsulated perfumes), or combinations thereof, improving the performance benefits of the composition, and / or allowing more efficient formulation of such benefit agents. The composition may include 0.0001% to 3%, preferably 0.0005% to 2%, more preferably 0.001% to 1%, or about 0.01% to about 0.5%, or about 0.05% to about 0.3% by weight of the composition of the deposition aid. The deposition aid may be a cationic or amphoteric polymer, preferably a cationic polymer.

[0164] Cationic polymers in general and their preparation methods are well known in the literature. Suitable cationic polymers include quaternary ammonium polymers known as "polyquaternium" polymers, as named in the International Nomenclature of Cosmetic Ingredients, such as Polyquaternium-6 (poly(diallyldimethylammonium chloride), Polyquaternium-7 (copolymer of acrylamide and diallyldimethylammonium chloride), Polyquaternium-10 (quaternized hydroxyethylcellulose), Polyquaternium-22 (copolymer of acrylic acid and diallyldimethylammonium chloride), etc.

[0165] The deposition aid may be selected from the group consisting of polyvinylformamide, partially hydroxylated polyvinylformamide, polyvinylamine, polyethyleneimine, ethoxylated polyethyleneimine, polyvinyl alcohol, polyacrylates, and combinations thereof.

[0166] The cationic polymer may comprise a cationic acrylate and / or a cationic methacrylate. Such polymers may be copolymers further comprising a non-ionic monomer such as, for example, acrylamide. The cationic polymer may be linear or crosslinked. The deposition aid may comprise a combination of a linear cationic polymer and a crosslinked cationic polymer.

[0167] The deposition aid can be added simultaneously with the delivery particles (e.g., simultaneously with the encapsulated benefit agent such as encapsulated perfume) or directly / independently into the consumer product composition. The weight average molecular weight of the polymer may be 500 Daltons to 5,000,000 Daltons, or 1,000 Daltons to 2,000,000 Daltons, or 2,500 Daltons to 1,500,000 Daltons, as measured by size exclusion chromatography against polyethylene oxide standards using Refractive Index (RI) detection. The weight average molecular weight of the cationic polymer may be 5,000 Daltons to 37,500 Daltons.

[0168] D. Fragrances and / or Fragrance Delivery Systems Perfume The treatment compositions of the present disclosure may include a perfume and / or a perfume delivery system, even if the benefit agent residue of the multimeric compound is derived from a perfume raw material.

[0169] The treatment composition of the present disclosure may contain other perfume raw materials, including PRMs that do not contain aldehyde or ketone moieties, for example, in undiluted or free form.For example, other PRMs can be provided in the premix composition and / or treatment composition according to the present disclosure as undiluted or free oils, even if they do not react with the multimeric precursor compound.Such mixtures may be desirable, for example, to provide a more suitable olfactory experience.

[0170] The treatment composition of the present disclosure may further comprise undiluted perfume, preferably undiluted perfume raw materials that do not contain aldehyde or ketone moieties.Preferably, the undiluted perfume comprises an alcohol-containing perfume raw material.Suitable alcohol-containing perfume raw materials are known to those skilled in the art and may include geraniol, citronellol, cinnamic alcohol, eugenol, etc.However, the undiluted perfume may further comprise free perfume raw materials that contain aldehyde and / or ketone moieties.

[0171] The treatment composition of the present disclosure may additionally or alternatively comprise a perfume delivery system. Such perfume delivery system may take the form of a polymer-assisted delivery system. Such perfume delivery system may take the form of an encapsulation, for example a core-shell encapsulation, in which the core comprises a perfume raw material and is surrounded by a polymer shell. The polymer shell may comprise a polymeric material derived from polyacrylate, polyurea, polyurethane, polysaccharide, polyvinyl alcohol, melamine, derivatives thereof, or combinations thereof. Additionally or alternatively, suitable perfume delivery systems may comprise known pro-perfume / pro-fragrance materials.

[0172] Other materials The treatment composition and / or even the premix composition of the present disclosure may contain unreacted reactants and / or decomposition products of the multimeric compounds described herein. For example, the treatment composition and / or the premix composition of the present disclosure may contain precursors or derivatives of amino acid moieties (such as parent amino acids), central linking groups that react with zero or one amino acid moieties, other free amino acids that contain benefit agent residues, free benefit agents (such as aldehyde or ketone-containing PRMs), or combinations thereof. The multimeric compounds and / or their amino acid moieties may react with other substances found in the formulation, for example, when the benefit agent residues are replaced with residues of different substances found in the formulation, especially when such substances contain aldehyde or ketone moieties. Although not intended, it is recognized that such reactions may occur in situ.

[0173] Premix The present disclosure further relates to certain premix compositions and methods of making such compositions. The premixes can be conveniently prepared prior to product formulation, and can even be prepared at one manufacturing site and shipped to another manufacturing site for product formulation.

[0174] The premix composition may comprise a multimeric precursor compound (wherein the multimeric precursor compound is as described above) and a benefit agent (wherein the benefit agent is as described above). The preferences expressed above for the multimeric compound, its components and / or its precursors equally apply here. The premix composition may comprise water. The premix composition may further comprise, preferably, a non-aqueous solvent, more preferably a hydroxyl-containing solvent, even more preferably ethanol.

[0175] For example, a premix composition may comprise a modified amino acid multimer precursor compound comprising a central linking group and 2-6 amino acid moieties each covalently bonded to the central linking group by a (distinct) heteroatom selected from the group consisting of O, S and N, preferably O, wherein the central linking group comprises 3-18 carbon atoms, each amino acid moiety comprises a carbon backbone comprising one or more carbon atoms, a carbonyl group comprising a carbon atom, and a nitrogen atom, and the heteroatoms are bonded directly to the carbon atom of the carbonyl group and to the central linking group, a benefit agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof, and optionally water.

[0176] For example, a premix composition can include a modified amino acid multimer precursor compound having a structure according to formula I': L[E] t Formula I', wherein L, E, and t are as defined above, with the proviso that the multimeric precursor compound comprises at least two E groups that are moieties according to formula II as defined above, with the further proviso that each A group of the moiety according to formula II is (a) H2N-, or (c) HG'(J) d N(H)-, G', J, and d are as defined above, and are selected from a benefit agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof, and optionally water. The preferences provided above for the remaining groups or indices other than A apply equally to formula I'.

[0177] For reasons of loading efficiency, it is preferred that the molar amount of the beneficial agent is reasonably matched to the molar amount of the amino acid moiety of the multimeric precursor compound.As mentioned above, one mole of the multimeric precursor compound typically contains 2 to 6 moles of amino acid moiety.The premix composition may contain the modified amino acid multimeric precursor compound and the beneficial agent in a molar ratio of 1:0.5X to 1:2X, preferably about 1:0.75X to about 1.5X, more preferably about 1:1X, where "X" represents the average number of equivalents of amino acid moiety per mole of precursor compound.

[0178] Even more specifically, for reasons of loading efficiency, it is preferred to reasonably match the molar amount of the benefit agent to the molar equivalent of the reactive functional group (e.g., amine group of the amino acid moiety) of the carrier molecule (here, the modified amino acid multimer precursor compound). For example, the premix composition may contain a molar ratio of the reactive functional group (e.g., amine group) of the modified amino acid multimer precursor compound to the benefit agent of about 3:1 to about 1:3, preferably about 2:1 to about 1:2, preferably about 1.5:1 to about 1:1.5, more preferably about 1.2:1 to about 1:1.2, and even more preferably about 1:1. Where the modified amino acid multimer precursor compound contains multiple attachment points, or multiple functional groups capable of forming such attachment points, for the benefit agent and optionally a second benefit agent, the premix composition may contain such functional groups of the modified amino acid multimer precursor compound and the benefit agent (optionally plus additional benefit agents which may also be attached to the precursor compound, e.g., as a hydrophobic material) present in a molar ratio of about 3:1 to about 1:3, preferably about 2:1 to about 1:2, preferably about 1.5:1 to about 1:1.5, more preferably about 1.2:1 to about 1:1.2, and even more preferably about 1:1.

[0179] The premix composition may be in the form of a neat fluid, with little or no water present. In such cases, it may be desirable to include a water scavenger in the premix, such as magnesium sulfate, and / or to physically remove the water, such as through molecular sieves or in a vacuum. The premix composition may contain less than about 10% water by weight of the premix composition, preferably less than about 5%, more preferably less than about 1%, and even more preferably less than about 0.1% water by weight. Low-moisture premix compositions may be particularly preferred when intended to be formulated into low-moisture product compositions, such as solids, such as pastilles, or compact formulations, such as unit dose compositions encapsulated in a water-soluble film. When the premix is ​​a low-water premix, the premix may contain about 1% to about 100%, preferably about 5% to about 100%, more preferably about 20% to about 100% modified amino acid multimer precursor compound by weight of the premix composition. When the premix is ​​a low water premix, the premix may comprise from about 0.01% to about 80%, preferably from about 0.01% to about 20%, of the modified amino acid multimer precursor compound by weight of the premix composition.When the premix is ​​a low water premix, the premix may comprise from about 0.01% to about 80%, preferably from about 0.01% to about 20%, of the benefit agent by weight of the premix composition.

[0180] The premix composition may comprise a non-aqueous solvent, more preferably a hydroxyl-containing solvent, even more preferably ethanol. The premix composition may comprise up to 50% by weight of the premix composition, preferably from about 5% to about 50% by weight, more preferably from about 10% to about 25% by weight, more preferably from about 10% to about 15% by weight of the solvent.

[0181] The premix composition may include water. The premix composition may be in the form of an emulsion, preferably an oil-in-water emulsion. When the premix is ​​in the form of an emulsion and includes water, the water may be present at a concentration of about 50% to about 95% by weight of the premix composition, preferably about 60% to about 90% by weight. When the premix includes water, the modified amino acid multimer precursor compound may be added at a concentration of about 0.01% to about 7.5% (by weight) of the premix composition. When the premix includes water, the benefit agent may be added at a concentration of about 0.01% to about 7.5% by weight of the premix composition.

[0182] In the premix composition, the modified amino acid multimer precursor compound and the benefit agent may react to form the modified amino acid multimer compound as described above. The precursor compound, the benefit agent and the modified amino acid multimer compound may all be in equilibrium. The formation of certain modified amino acid multimer compounds, such as those containing imines, produces water through the condensation process, so if the premix contains water, the equilibrium may lean towards the reactants of the reaction (e.g., the precursor compound and the benefit agent). Conversely, if the premix is ​​substantially free of intentionally added water, there may be relatively more modified amino acid multimer compounds, but it is recognized that some water will form as a result of the condensation reaction. When the formation of the modified amino acid multimer compound involves 1,4 addition, it is believed that the equilibrium does not depend on water, but rather on the balance between entropic and enthalpic contributions.

[0183] The sum of the weight percentages of the modified amino acid multimer precursor, benefit agent, and, if present, the modified amino acid multimer compound, can be from about 10% to about 100%, preferably from about 25% to about 100%, preferably from about 50% to about 100%, and more preferably from about 75% to about 100% by weight of the premix composition.

[0184] A premix composition or a portion thereof can be obtained by combining from about 1 part by weight to about 99 parts by weight, preferably from about 5 parts by weight to about 80 parts by weight, of a modified amino acid multimer precursor compound with from about 1 part by weight to about 99 parts by weight, preferably from about 5 parts by weight to about 80 parts by weight of a benefit agent, the resulting mixture being understood to comprise a total of 100 parts by weight.

[0185] The premix composition may include multiple precursors, multiple benefit agents, and / or multiple modified amino acid multimeric compounds. The premix composition may further include additional agents that do not react to form modified amino acid multimeric compounds according to the present disclosure. For example, the premix composition may include additional PRMs, surfactants, solvents, antioxidants, or other processing or stabilization aids.

[0186] The premix composition may also include a surfactant, preferably a non-ionic surfactant, which may aid in the stability of the premix composition and / or the emulsification process.

[0187] The present disclosure further relates to a method of making such a premix composition. The method may include combining a modified amino acid multimer precursor as described herein with a benefit agent as described herein, the benefit agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof. The materials may be combined in the ratios provided above. The method may include removing or otherwise binding free water, which may help drive the reaction in the premix toward the product (e.g., a multimer compound). If the premix composition includes water, the precursor compound and water may preferably be combined before the benefit agent is added. Alternatively, the benefit agent and water may be mixed before the benefit agent is added.

[0188] Method for preparing the treatment composition The present disclosure relates to a process for making any of the compositions described herein. The process for making a treatment composition, which may be a consumer product, preferably a fabric care composition, may include combining the modified amino acid multimer compound described herein with an auxiliary material described herein.

[0189] The modified amino acid multimer compounds can be combined with such auxiliary materials by methods including mixing and / or spraying.

[0190] The composition of the present disclosure can be formulated in any suitable form and prepared by any process selected by the formulator.The modified amino acid multimer compound and auxiliary materials can be combined in a batch process, a circulation loop process, and / or an in-line mixing process.The equipment suitable for use in the method disclosed herein may include a continuous stirred tank reactor, a homogenizer, a turbine agitator, a recirculation pump, a paddle mixer, a high shear mixer, a static mixer, a plow shear mixer, a ribbon blender, a vertical shaft granulator and a drum mixer (both batch and, if available, in a continuous process configuration), a spray dryer, and an extruder.

[0191] For example, a method for producing a treatment composition can include combining a modified amino acid multimer compound according to the present disclosure with a base composition, preferably a liquid base composition, including auxiliary ingredients. This process can be carried out, for example, in a batch process or an in-line mixing process, preferably an in-line mixing process.

[0192] The method of producing a treatment composition may include combining a modified amino acid multimer precursor compound, a benefit agent, and an auxiliary component, as described herein. Preferably, the auxiliary component is part of the base composition, and the multimer precursor compound and the benefit agent are each added to the base composition as separate charges. The separate charges may be added sequentially (e.g., consecutively) or substantially simultaneously. Preferably, the base composition is a liquid. This process may be carried out, for example, in a batch process or an in-line mixing process, preferably an in-line mixing process.

[0193] The method of making the treatment composition may include adding a premix to a base composition. The premix composition may include a modified amino acid multimer precursor compound and a benefit agent, as described herein. The premix composition may be obtained by combining a modified amino acid multimer precursor compound and a benefit agent, as described herein. The premix composition may include a modified amino acid multimer compound according to the present disclosure, for example, by reaction of the precursor compound with a benefit agent. The premix composition may include a mixture of a modified amino acid multimer precursor compound, a benefit agent, and a modified amino acid multimer compound. The premix may optionally contain water. This process may be carried out, for example, in a batch process or an in-line mixing process, preferably an in-line mixing process. The premix may be particularly preferred when making a treatment composition that is or will be in a solid form, such as a PEG-based pastille. In such cases, removal or reduction of water from the premix may be useful, for example, via a water scavenger, such as magnesium sulfate, or via the use of molecular sieves or stripping in vacuum.

[0194] How to treat the surface The present disclosure further relates to methods of treating a surface (eg, a surface of an article) with a treatment composition according to the present disclosure. Such methods may provide cleaning, conditioning, hygiene, and / or cooling benefits.

[0195] Suitable surfaces may include fabrics (including clothing, towels, or linens), hard surfaces (such as tile, porcelain, linoleum, or wood floors), dishware, hair, skin, or mixtures thereof.

[0196] The method may include contacting the article or surface with a treatment composition of the present disclosure, optionally in the presence of water, and may further include rinsing and / or drying the article or surface. The treatment composition may be in undiluted form or may be diluted with a liquid, such as a cleaning or rinsing liquid. The treatment composition may be diluted with water before, during, or after contact with the surface or article. The surface or article may be optionally washed and / or rinsed before and / or after the contacting step.

[0197] The method for treating and / or cleaning a surface may comprise the following steps. a) optionally cleaning, rinsing and / or drying the surface; b) contacting the surface with a treatment composition described herein, optionally in the presence of water; c) optionally cleaning and / or rinsing the surface; and d) Optionally, drying by passive drying and / or by active methods such as a washer dryer.

[0198] For purposes of the present invention, cleaning includes, but is not limited to, scrubbing and mechanical agitation. Fabrics may include most any fabric that can be laundered or treated under normal consumer or industrial use conditions.

[0199] The liquid that may contain the disclosed composition may have a pH of about 3 to about 11.5. When diluted, such compositions are typically used at a concentration of about 500 ppm to about 15,000 ppm in solution. When the cleaning solvent is water, the water temperature typically ranges from about 5° C. to about 90° C., and when the surface is a part of a fabric, the weight ratio of water to fabric is typically about 1:1 to about 30:1.

[0200] The present disclosure further discloses a process of treating a surface or article, preferably a fabric, with an aqueous treatment solution comprising a modified amino acid multimeric compound according to the present disclosure, preferably wherein the benefit agent residue is a residue of a perfume raw material or an antimicrobial agent, preferably a residue of a perfume raw material. The method may comprise the step of contacting the surface or article, preferably the fabric, with the aqueous solution. The multimeric compound may be present in the aqueous solution at a concentration of about 0.001 ppm (e.g., 1 ppb) to about 1000 ppm by weight.

[0201] The present disclosure further discloses a process for treating a surface or article, preferably a fabric, with an aqueous treatment solution comprising a modified amino acid multimer precursor compound according to the present disclosure and a benefit agent according to the present disclosure. The benefit agent may be a perfume raw material or an antimicrobial agent, preferably a perfume raw material. The method may include contacting the surface or article, preferably a fabric, with the aqueous solution. The multimer precursor compound may be present in the aqueous solution at a concentration of about 001 ppm (e.g., 1 ppb) to about 1000 ppm by weight.

[0202] use The present disclosure relates to the use of modified amino acid multimers as described herein to provide freshness benefits, particularly when the modified amino acid multimers comprise residues of flavor raw materials, when part of a treatment composition.

[0203] The present disclosure relates to the use of modified amino acid multimeric compounds described herein to provide antimicrobial benefits, particularly when the modified amino acid multimeric compounds comprise fragments of antimicrobial agents, when part of a treatment composition.

[0204] The present disclosure relates to the use of modified amino acid multimeric compounds as described herein to provide malodor control benefits, particularly when part of a treatment composition.

[0205] combination Specifically contemplated combinations of the present disclosure are described herein in the following alphabetical sections, which are exemplary in nature and not intended to be limiting.

[0206] A. A treatment composition comprising a processing adjunct and a modified amino acid multimeric compound, the multimeric compound comprising a central linking group and 2-6 amino acid moieties each covalently bonded to the central linking group by a heteroatom selected from the group consisting of O, S, and N, preferably O, the central linking group comprising 3-18 carbon atoms, each amino acid moiety comprising a carbon backbone comprising one or more carbon atoms, a carbonyl group comprising a carbon atom, and a nitrogen atom, the heteroatoms being bonded directly to a carbon atom of the carbonyl group and to the central linking group, at least one amino acid moiety comprising an organic moiety covalently bonded to a nitrogen atom of the amino acid moiety, the organic moiety comprising a benefit agent residue, the benefit agent being released upon cleavage of one or more bonds connecting the benefit agent residue to the amino acid moieties, the benefit agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof. B. A treatment composition comprising a processing adjunct and a modified amino acid multimeric compound, the multimeric compound comprising a central linking group and 2-6 amino acid moieties each covalently bonded to the central linking group, the central linking group comprising 3-18 carbon atoms, each amino acid moiety comprising a carbonyl group at its C-terminus, the carbonyl group comprising a carbon atom, the carbonyl carbon atom being bonded to a heteroatom of the central linking group, the heteroatom being selected from the group consisting of O, S or N, each amino acid moiety further comprising a nitrogen atom at its N-terminus, at least one amino acid moiety comprising a benefit agent residue bonded to the nitrogen atom at the N-terminus of the at least one amino acid moiety, the benefit agent being released upon cleavage of one or more bonds linking the benefit agent residue to the amino acid moiety, the benefit agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof. C. The treatment composition of any one of paragraphs A or B, wherein the carbon backbone of each amino acid moiety independently contains 1 to 9 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, more preferably 1 to 2 carbon atoms, and even more preferably 1 carbon atom. D. The treatment composition of any of paragraphs A-C, wherein at least one, preferably at least two, and more preferably all, of the amino acid moieties are derived from a proteinogenic amino acid, preferably a proteinogenic amino acid independently selected from cysteine, glycine, aspartic acid, glutamic acid, lysine, or combinations thereof, more preferably cysteine. E. The treating composition of any one of paragraphs A-D, wherein the amino acid moieties are derived from amino acids having the same identity, preferably derived from proteinogenic amino acids having the same identity. F. The treatment composition of any one of paragraphs A-E, wherein at least two, and preferably all, of the amino acid moieties comprise a benefit agent residue. G. A processing composition comprising a processing aid and a modified amino acid multimer compound, the modified amino acid multimer compound having Formula I: L[E] t Formula I wherein t is independently an integer from 2 to 6, preferably from 2 to 5, more preferably from 2 to 4, more preferably from 2 to 3, and more preferably 2; L is a polyvalent central linking group containing from 3 to 18 carbon atoms; and each E group is independently -GH, -GX, or a group represented by formula II

[0207] [ka] (a) selected from a moiety conforming to provided that the multimeric compound includes at least two E groups that are moieties according to formula II; * represents the point of attachment of the E group to L, the value of x is 1 to 9, preferably 1 to 6, more preferably 1 to 3, even more preferably 1 to 2, and even more preferably 1; each G is independently -O-, -N(R 3 )-, or -S-, preferably each G group is the same and each R 3 is, if present, independently selected from H or a monovalent moiety having a molecular weight of 14 to 881 Da, preferably 41 to 255 Da, where X, if present, is a suitable charge-balancing counterion, and each R 1are independently selected from H or a monovalent moiety having a molecular weight of 15 to 507 Da, preferably R 1 is selected from the side groups of proteinogenic amino acids or monovalent moieties having a molecular weight between 15 and 142 Da, and each R 2 are independently selected from H and a monovalent moiety having a molecular weight of 15 to 1000 Da, preferably 15 to 507 Da, more preferably 15 to 142 Da, and preferably R 2 is H, each A group is a monovalent nitrogen-containing moiety, and at least one A group comprises an independently selected group, is a benefit agent residue linked to the remainder of the A group by one or more bonds, and the benefit agent is released upon cleavage of the one or more bonds, and the benefit agent comprises an aldehyde moiety, a ketone moiety, or a combination thereof. H. Each A group is independently: (a) HN-; (b) Z ** N-, (in the formula, ** represents the connecting bond between the nitrogen atom and the carbon atom of the Z group, the connecting bond being either (i) a double bond, thereby forming an imine bond, or (ii) a single bond formed from a 1,4-addition when the benefit agent from which the benefit agent residue is derived contains an alpha-beta unsaturated carbonyl-containing moiety that is an aldehyde or ketone moiety; Z ** The nitrogen atom of the N-group is further bonded to a hydrogen (-H), (c) HG'(J) d N(H)-, and (d)

[0208] [ka] and the index d is selected from 1 to 3, preferably d is 2 to 3, more preferably d is 2, wherein each G' is independently -O-, -S-, or -N(R 7 )-, preferably G' is -O-, and each R 7 R1, when present, is independently selected from -H or a monovalent moiety having a molecular weight of about 15 to about 255 Da, preferably R 7is a monovalent moiety having a molecular weight of about 15 to about 142 Da, more preferably a monovalent moiety having a molecular weight of about 15 to about 30 Da, the Z group contains 4 to 34 carbon atoms, N and G' are attached to the same carbon atom of the Z group, and each J is independently selected from the group C(R 9 )2-O-, and -N(R 9 ), and preferably each J is selected from the group consisting of C(R 9 )2, and each R 9 are independently selected from H or a monovalent moiety having a molecular weight of 14 to 990 Da, more preferably R 9 is selected from H or a monovalent moiety having a molecular weight between 14 and 186 Da, and even more preferably R 9 is H, with the proviso that the first R 9 and the second R 9 may be taken together as a divalent substituent where possible, and preferably the divalent substituent is selected from the group consisting of fused rings, spirocyclic rings, and ═N(R 7 ), ═O, and ═S; R 7 is as defined above, if present, and at least one A group is independently selected from (b) or (d), more preferably at least one A group is selected from (b) Z ** N-, and even more preferably, all A groups are selected from (b) Z ** The treatment composition of paragraph G, wherein each Z group is selected from N-, and each Z group is an independently selected benefit agent residue. I. At least one A group is selected from the group consisting of (b) Z ** N-, Z ** The Z group of the N-moiety is

[0209] [ka] and mixtures thereof, 4 (R 5 ) and -CH(R 8 )CH2C(O)R 5Each moiety represents a residue of a benefit agent, the residue of the benefit agent having a molecular formula that differs from the molecular formula of the benefit agent only by having one less O atom or one more H atom, the benefit agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof, preferably R 4 is independently selected from a monovalent organic moiety, and 5 and R 8 are independently selected from the group consisting of hydrogen and monovalent organic moieties, more preferably wherein the benefit agent is a perfume raw material containing from 4 to 34 carbon atoms, with the proviso that R 4 and R 5 or R 8 and R 5 may be linked to form a cyclic divalent organic moiety. The JZ group has the structure:

[0210] [ka] The treatment composition of any of paragraphs GI, wherein the benefit agent residue has the formula: K. The treatment composition of any of paragraphs G-J, wherein at least one of the following is true: two or more A groups comprise a benefit agent residue, and for a given compound, the identities of the A groups are the same, and for a given compound, the identities of the A groups are different, and wherein, for a given compound, the identity of the Z group is the same, and / or for a given compound, the identities of the Z groups are different. L. At least one R 2 R 2 The treatment composition of any of paragraphs GK, wherein is a monovalent moiety having a molecular weight from 54 to 1000 Da. M. The treatment composition of any one of paragraphs A through L, wherein the central linking group contains from 3 to 16 carbon atoms, preferably from 5 to 12 carbon atoms, and more preferably from 8 to 12 carbon atoms. N. The treatment composition of any one of paragraphs A through M, wherein the central linking group is a divalent, trivalent, or tetravalent organic moiety, preferably divalent. O. The treatment composition of any one of paragraphs A-N, wherein the central linking group is derived from a polyhydric alcohol, preferably selected from a diol, triol, or pentaerythritol, and even more preferably selected from 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, glycerol; or pentaerythritol.

[0211] P. The treatment composition of any of paragraphs A-O, wherein the benefit agent residue is a residue of a benefit agent selected from a perfume raw material, an antimicrobial agent, a pesticide, an insect repellent, an antifungal agent, a herbicide, a hueing dye, an antioxidant, a non-perfume functional material, or a combination thereof, preferably a perfume raw material, an antimicrobial agent, or a combination thereof.

[0212] Q. The treatment composition of any of paragraphs A-P, wherein the benefit agent is a perfume raw material, preferably a perfume raw material selected from the group consisting of methyl nonyl acetaldehyde, benzaldehyde. Floralozone, isocyclocitral, tripral (ligustral), presylchemone B, lilial, decyl aldehyde, undecylenic aldehyde, cyclamen homoaldehyde, cyclamen aldehyde, dupical, oncidal, adoxal, melonal, calypsone, anisaldehyde, heliotropin, cumin aldehyde, scentenal, 3,6-dimethylcyclohex-3-ene-1-carbaldehyde, satin aldehyde, canthoxal, vanillin, ethyl vanillin, cinnamic aldehyde, cis-4-decenal, trans-4-decenal cis-7-decenal, undecylenic aldehyde, trans-2-hexenal, trans-2-octenal, 2-undecenal, 2,4-dodecadienal, cis-4-heptenal, Florydral, butylcinnamaldehyde, limoneral, amylcinnamaldehyde, hexylcinnamaldehyde, citronellal, citral, cis-3-hexen-1-al, nerolion, 4-(4-methoxyphenyl)butan-2-one, 1-naphthalen-2-ylethanone, nectaryl, trimofix O, fluramone, delta-damascone, beta-damascone, alpha-damascone, methyl ionone, 2-hexylcyclopent-2-en-1-one, galbascone, and mixtures thereof. R. The treatment composition of any of paragraphs A-Q, wherein the modified amino acid multimeric compound comprises a polymeric component of three or more repeat units. S. The treatment composition of any of paragraphs A-R, wherein the adjunct ingredients include one or more of surfactants, conditioning actives, deposition aids, rheology modifiers or structurants, acid inhibitors, bleaching systems, stabilizers, builders, chelating agents, dye transfer inhibitors, dispersants, enzymes, enzyme stabilizers, catalytic metal complexes, polymeric dispersants, mud and soil removal / anti-redeposition agents, brighteners, suds suppressors, silicones, hueing agents, aesthetic dyes, neat fragrances, fragrance delivery systems, structural elastomers, carriers, hydrotropes, processing aids, anti-agglomerating agents, coatings, formaldehyde scavengers, and / or pigments. T. The treatment composition of any of paragraphs A-S, wherein the adjunct ingredients include a conditioning active, preferably the conditioning active includes a quaternary ammonium ester compound, more preferably the quaternary ammonium ester compound is present in a concentration of from about 2% to about 35%, preferably from about 4% to about 25%, more preferably from about 5% to about 20%, preferably from about 6% to about 15%, more preferably from about 7% to about 12% by weight of the treatment composition. U. The treatment composition of any of paragraphs A-T, wherein the treatment composition further comprises a neat fragrance, preferably a neat fragrance comprising an alcohol-containing fragrance raw material, an ester-containing fragrance raw material, or a combination thereof. V. The treatment composition of any of paragraphs A-U, wherein the treatment composition is a consumer product, preferably a consumer product selected from a fabric care composition, a hard surface cleaner composition, a dish care composition, a hair care composition, a body cleansing composition, or mixtures thereof, even more preferably a fabric care composition. W. The treatment composition of any of paragraphs A-V, wherein the treatment composition is in the form of a liquid composition, a granular composition, a hydrocolloid, a single compartment pouch, a multi-compartment pouch, a dissolvable sheet, pastilles or beads, a fibrous article, a tablet, a stick, a bar, a flake, a foam / mousse, a nonwoven sheet, or a mixture thereof. X. The treatment composition of any of paragraphs A through W, wherein the multimeric compound is present in the treatment composition at a concentration of from about 0.001% to about 30% (by weight) of the treatment composition. Y. The modified amino acid multimer compound according to any one of paragraphs A to X. Z. A modified amino acid multimer precursor compound having a structure according to formula I', L[E] t Formula I', wherein L, E, and t are defined above, with the proviso that the multimeric precursor compound comprises at least two E groups which are moieties according to formula II defined above, with the further proviso that each A group of the moiety according to formula II is HN-, or (c) HG'(J) d N(H)-, wherein G', J, and d are defined as above. AA. A premix composition comprising a modified amino acid multimer precursor compound as described in paragraph Z, a benefit agent, and optionally water, wherein the benefit agent comprises an aldehyde moiety, a ketone moiety, or a combination thereof, and the premix composition optionally further comprises a non-aqueous solvent, more preferably a hydroxyl-containing solvent, even more preferably ethanol. BB. A method for producing a treatment composition described in any of Paragraphs A-X, the method comprising at least one of the following steps: (a) combining a modified amino acid multimer compound with an auxiliary component, preferably where the auxiliary component is part of a base composition; (b) mixing a premix composition described in Paragraph AA with the auxiliary component, preferably where the auxiliary component is part of the base composition; (c) combining a modified amino acid multimer precursor compound, a benefit agent, and the auxiliary component, preferably where the auxiliary component is part of the base composition, and the modified amino acid multimer compound and the benefit agent are each added as separate inputs to the base composition. CC. A method of treating an article or surface, the method comprising treating the article or surface with a treatment composition described in any of paragraphs A-X, optionally in the presence of water, and optionally further comprising rinsing and / or drying the article or surface.

[0213] Test Method It will be understood that the values ​​of each of the parameters of the inventive subject matter claimed and described herein should be determined using the test methods disclosed in the Test Methods section of this application.

[0214] HLB value of nonionic surfactants Nonionic surfactants can be classified by the balance between the hydrophilic and lipophilic moieties in the surfactant molecule. The hydrophilic-lipophilic balance (HLB) scale, devised by Griffin in 1949, is a scale of 0 to 20 (20 being hydrophilic) used to characterize the properties of surfactants. The HLB of a surfactant can be calculated as follows: HLB=20 * Mh / M (where Mh is the molecular weight of the hydrophilic portion of the molecule and M is the molecular weight of the entire molecule, and the results are given on a scale of 0 to 20). An HLB value of 0 corresponds to a completely lipophilic / hydrophobic molecule, and a value of 20 corresponds to a completely hydrophilic / lipophobic molecule. See Griffin, WC Calculation of HLB values ​​of Nonionic Surfactants, J. Soc. Cosmet. Chem. 1954, 5, 249-256. HLB values ​​of commonly used surfactants are readily available from the literature (e.g., the HLB index in McCutcheon's Emulsifiers and Detergents, MC Publishing Co., 2004). The HLB value of a mixture of surfactants can be calculated as a weighted average of the HLB values ​​of the surfactants.

[0215] Test Methods for Determining logP Logarithm of the octanol / water partition coefficient (logP) values ​​are calculated for materials as described herein (such as alcohol versions of hydrophobes / Q groups or PRMs).

[0216] The logP values ​​of individual PRMs were calculated using the Consensus logP Computational Model, version 14.5 (Linux), available from Advanced Chemistry Development Inc. (ACD / Lab), Toronto, Canada, which yields unitless logP values. The ACD / Labs Consensus logP Computational Model is part of the ACD / Labs model suite.

[0217] Preparation of Test Fabric Enhancer / Softener Compositions Provide 7.5% by weight N,N-di(tallowoyloxyethyl)-N,N-dimethylammonium chloride in water mixture. Premix fluid as above, premix emulsion as above, or two separate undiluted fluids (one being a multimeric precursor such as modified amino acid, the other being a benefit agent such as one or more perfume raw materials) are added in an amount such that the concentration of benefit agent or benefit fragment in the fabric softener is about 0.3% by weight of the final fabric softener composition. Mix the mixture at 350 rpm for 5 minutes using an IKA RW20DSl mixer, model RW20DSl, and an IKA R1 342 impeller blade. Add structurant and deposition aid, and mix for 10 minutes. Add water as needed to standardize the concentration of N,N-di(tallowoyloxyethyl)-N,N-dimethylammonium chloride between the test legs to 7.3% by weight, and mix for 5 minutes. Adjust pH to 2-3 with HCl, if necessary.

[0218] Preparation of Test Fabric Detergent Compositions To 97.58 parts by weight of TIDE Original Scent liquid detergent formulated without TIDE OS fragrance, add 2.42 parts by weight of the multimeric compound premix fluid. The amount is selected so that the concentration of the selected benefit agent or benefit agent fragment in the final detergent is about 1% by weight after the fabric treatment composition. The mixture is agitated for 10 minutes at 350 rpm using an IKA RW20DSl mixer, model RW20DSl, and an IKA R1 342 impeller blade.

[0219] Fabric Preparation Method To prepare fabric for headspace analysis testing, fabric samples (100% cotton terry cloth, item number ITL 1022-15PGP, Calderon Textiles, Inc. 6131 W.80 th St., Indianapolis, IN 46278, desized and conditioned with three wash cycles of detergent and fabric softener, then treated with detergent or fabric softener in a manner consistent with North American consumers via a clothes mini washer, full-scale washer, and clothes dryer. Prior to headspace GCMS analysis (see methods below), fabrics are equilibrated at 21.1°C and 50% relative humidity for 12-24 hours unless otherwise noted. Ballast loads consist of swatches of cotton and polycotton knits, 20 x 20 in (50 x 50 cm) in size.

[0220] Cleaning treatment conditions In the following fabric enhancer / softener composition performance test, fabrics are treated with the following wash process conditions: Wash: 12 minute agitation, 30.6°C. Rinse: 2 minute agitation, 15.5°C. Water hardness: 137 ppm. Water: 7.6 pH. Fabric load weight: 290 g. Tumble dry setting: 50 minutes high, cotton. Detergent dosage: 9.65 g. Fabric softener dosage: 5.71 g.

[0221] The detergent used was TIDE Original Scent (manufactured by The Procter & Gamble Company), a fragrance-free liquid.

[0222] Headspace analysis on fabric The following procedure is used to determine the level of perfume ingredients in the headspace on the fabric.

[0223] The following equipment is used: Gas Chromatograph 7890B with Mass Selective Detector (5977B) (MSD) and ChemStation Quantitative Package, Gerstel Multipurpose Sampler with Solid Phase Microextraction (SPME) probe or similar system, Divinylbenzene / Carboxen / Polydimethylsiloxane SPME fiber from Supleco part #57298-U (or similar fiber), nominal diameter 30 m x 0.25 mm, film thickness 0.25 μm, J&W 122-5532UI DB-5, 20 mL headspace vial.

[0224] To prepare the fabric for analysis, cut three 2.54 cm x 5.08 cm cotton swatches from the cotton terry prepared and treated as described above. Place each piece into a 20 mL headspace vial and cap.

[0225] The parameters of the Gerstel autosampler are as follows: SPME-from incubator, incubation temperature-65 °C., incubation time-10.00 min. Sample parameters, vial penetration-22.00 mm, extraction time-5.00 min, initial penetration-54.00 mm, desorption time-300 s. The GC oven parameters for the front SS inlet He are as follows: mode-splitless, heater: 270 °C, GC run time-14.28 min. For the oven, initial temperature-40 °C, hold time-0.5 min, heating program-rate of 17 °C / min, temperature of 270 °C, hold time of 0.25 min. The MSD parameters are as follows: run in scan mode with a minimum range of 35-350 m / z.

[0226] Generate a calibration curve from standard benefit materials. Calculate the headspace mass using the calibration curve for each perfume ingredient in the ChemStation software (or similar quantitative software). EXAMPLES

[0227] The examples provided below are intended to be illustrative and not limiting in nature.

[0228] Synthesis Examples The following Synthesis Examples 1-5 illustrate the synthesis of exemplary pro-benefit agent compounds (eg, Synthesis Example 1) and their amine-containing pro-fragrance precursors (eg, Synthesis Example 1′) in accordance with the present disclosure.

[0229] For consistency and illustrative / comparison purposes, each example reacts a different undiluted pro-fragrance precursor with the same perfume raw material, cyclamen aldehyde (containing an aldehyde moiety), having the following structure: As a further example (formed by the addition of 1,4), Synthesis Example 1B forms a pro-benefit agent compound with δ-damascene, which contains a ketone moiety. The structure of the PRM is shown below:

[0230] [ka]

[0231] However, it is understood that other aldehyde- or ketone-containing benefit agents according to the present disclosure may also result in the formation of suitable pro-benefit agent compounds, some of which are exemplified and tested in the performance examples below.

[0232] It is also understood that the synthetic examples may be formulated into the treatment composition as a liquid premix emulsion, or as a neat fluid, or as a liquid premix fluid as described above, however, for the performance and stability examples reported below, all synthetic examples are assumed to be formulated directly into the treatment composition as a liquid premix fluid unless otherwise indicated.

[0233] For each synthesis example, the resulting pro-benefit agent compound (eg, modified amino acid ester molecule) is exemplified along with cyclamen aldehyde (or delta-damascone, in the case of synthesis example 1B) and shown in Table D below.

[0234] Method for preparing modified amino acid multimer compounds In the following synthetic examples, materials are generally obtained / available from Sigma-Aldrich (St. Louis, MO, USA) except where indicated below. Amino acids are generally provided in >98% or even >99% purity. Alcohols are generally provided in >97%, >98%, or even >99% purity. Cyclamen aldehyde (e.g., Sigma-Aldrich) is provided in >95% pure. δ-Damascone is available from Firmenich (Geneva, Switzerland).

[0235] General Method A: General Preparation of Multimeric Precursor Compounds To prepare multimeric precursor compounds from amino acids and alkyl alcohols (e.g., glycerol), a round-bottom flask is charged with approximately 1 equivalent of the free base amino acid starting material. To the flask, the indicated equivalents of alcohol and approximately 1.2 equivalents of p-toluenesulfonic acid monohydrate (PTSA) or methanesulfonic acid (MsOH) are added. The flask is then diluted with toluene and refluxed for 12 hours using a Dean-Stark apparatus. The solvent is removed in vacuo and the resulting crude material is dissolved in chloroform. The solution is neutralized with Et3N, then washed three times with NaOH and dried with MgSO4. The solvent is removed and the washed material is diluted with cyclohexane and stored at 0°C for 12 hours. The eluent is collected to give the desired modified amino acid (ester) multimeric precursor compound.

[0236] General Method B: General Preparation of Modified Amino Acid Multimeric Compounds Place 1 equivalent of modified amino acid multimer precursor in a round bottom flask. Add 1 equivalent of either cyclamen aldehyde or δ-damascene to the flask. Add 20% by weight of 4 Å molecular sieves to the fluid and stir the mixture for 12 hours. Filter the resulting mixture using a Pyrex 36060-30M Brand 36060 fritted funnel and use directly.

[0237] Synthesis Example 1A Synthesis Example 1' was prepared as described in General Method A, except that 10 g of DL-valine, 6.0 g of 1.10-hexadecanol, and 8.2 g of PTSA·H2O were used. The isolated fluid of Synthesis Example 1' was then mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 1A. The isolated fluid 1A was: 1 It appears to be stable for several months by 1 H NMR.

[0238] Synthesis Example 1B Synthesis Example 1' was prepared as described in Synthesis Example 1A. The isolated fluid of Synthesis Example 1' was then mixed with δ-Damascone as described in General Method B to obtain Synthesis Example 1B. The isolated fluid 1B was 1 It appears to be stable for several months by 1 H NMR.

[0239] Synthesis Example 2 Synthesis Example 2' was prepared as described in General Method A, except that 10 g of L-valine, 5.3 g of 1.12-octadecanol, and 8.2 g of PTSA·H2O were used. The isolated fluid of Synthesis Example 2' was then mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 2. Separate Fluid 2 was 1 It appears to be stable for several months by 1 H NMR.

[0240] Synthesis Example 3 Synthesis Example 3' was prepared as described in General Method A, except that 10 g of L-valine, 1.7 g of 1-pentaerythritol, and 20 g of PTSA·H2O were used. The isolated fluid of Synthesis Example 3' was then mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 3. Separate Fluid 3 was: 1 It appears to be stable for several months by 1 H NMR.

[0241] Synthesis Example 4 Synthesis Example 4' was prepared as described in General Method A, except that 26 g of L-valine, 5.0 g of 1-glycerol, and 44 g of PTSA·H2O were used. The isolated fluid of Synthesis Example 4' was then mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 4. Separate Fluid 4 was 1 It appears to be stable for several months by 1 H NMR.

[0242] Synthesis Example 5 Synthesis Example 5' was prepared as described in General Method A, except that 20 g of L-phenylalanine, 9.8 g of 1.12-phenylalanine, and 25 g of PTSA·H2O were used. The isolated fluid of Synthesis Example 5' was then mixed with δ-damascene as described in General Method B to obtain Synthesis Example 5. The isolated fluid 5 was 1 It appears to be stable for several months by 1 H NMR.

[0243] Structures of synthetic examples. Table D below shows the structures of Synthetic Examples 1-5, as well as their precursor compounds (denoted with "'").

[0244] [Table 3]

[0245] In the following examples, pro-benefit agent precursor compounds (e.g., amino acid ester molecules) and the indicated perfume raw materials are mixed substantially according to a procedure similar to that found in the Test Methods section above ("Preparation of Premix Fluids"). Despite the differences in preparation methods between the synthesis and performance examples (e.g., made with different pro-benefit agents), the inputs and outputs with respect to the pro-benefit agent compounds are substantially the same.

[0246] Performance Examples In the following performance examples 1-3, treatment compositions containing neat perfume oil or pro-benefit agent compounds according to the present disclosure (e.g., based on modified amino acid multimers) are compared through treatment cycles in an automatic washing machine according to the fabric treatment method provided above. After treatment, the fabrics are tested for headspace analysis according to the test method provided above. The data below demonstrate the benefits provided by hydrophobically modified amino acid esters and their interaction with benefit agents via imines or 1,4-adducts in the delivery of the benefit agents.

[0247] Performance Examples 1. Application in liquid fabric enhancers with a series of modified amino acid esters. To further evaluate these materials, various benefit agent materials were tested. In the following examples, equimolar concentrations of aldehyde benefit agents, as described in each test leg, are provided to precursor amino acids as described above, and then formulated into test fabric enhancer / softener compositions prepared as described in the test method above. The test fabrics are prepared, washed, and tested for headspace analysis on the fabric according to the test method above.

[0248] For rows labeled "Synthetic Example 1," etc. in both Table 1 and subsequent tables, it is understood that a sample was prepared substantially according to the methods and precursors provided in the recited Synthetic Example, but using not only cyclamen aldehyde or delta-damascene but also the benefit agent material listed in the Performance Table (at equimolar concentrations with the precursor modified amino acid ester) and formulated as a premix fluid as detailed above.

[0249] The results of the above headspace analysis fabric tests are shown in Table 1 below.

[0250] [Table 4] a The formulation was 0.3% by weight and was composed of: 10% by weight methylnonylacetaldehyde, 40% by weight PT Bucinal, 20% by weight Precyclemon B, and 30% by weight Floralozone.

[0251] As shown in Table 1, the hydrophobically modified amino acid ester 1-2 provided an improvement in total headspace over the undiluted feed.

[0252] Additionally, increasing the carbon chain length provides an improvement in the overall delivery of the benefit agent, as exemplified by Synthetic Example 2. Synthetic Example 2 showed the greatest improvement in headspace. Overall, the synthetic examples show similar trends in the delivery of the individual benefit agents.

[0253] Performance Example 2. Comparative Example of Dimer, Trimer and Tetramer Liquid Fabric Enhancer Formulations In the following examples, equimolar concentrations of aldehyde benefit agent as described in each test leg are provided to precursor amino acids as described above, and then formulated into test fabric enhancer / softener compositions prepared as described in the test method above. Test fabrics are prepared, washed, and tested for headspace analysis on fabric according to the test method above. The results of headspace analysis on fabric are shown in Table 2.

[0254] [Table 5] a The formulation was 0.3% by weight and was composed of: 10% by weight methylnonylacetaldehyde, 40% by weight PT Bucinal, 20% by weight Precyclemon B, and 30% by weight Floralozone.

[0255] As shown in Table 2, the modified amino acid materials offer significant advantages over neat oil or free base amino acids. Furthermore, for this particular performance test, the phenylalanine dimer outperformed either the trimer or tetramer.

[0256] The propensity of individual benefit agents varies across different modified amino acids, therefore it seems reasonable to construct single or mixtures of systems containing combinations of benefit agents, amino acids, and (preferably hydrophobic) central linking groups to provide the desired benefits.

[0257] Performance Example 3. Comparative Example of Modified Amino Acids in Detergent Compositions. In the following examples, equimolar concentrations of aldehyde benefit agent as described in each test leg are provided to precursor amino acids as described above, and then formulated into test fabric detergent compositions prepared as described in the test method above. Test fabrics are prepared, washed, and tested for headspace analysis on fabric according to the test method above. The results of headspace analysis on fabric are shown in Table 3.

[0258] [Table 6] a The formulation was 0.3% by weight and was composed of: 10% by weight methylnonylacetaldehyde, 40% by weight PT Bucinal, 20% by weight Precyclemon B, and 30% by weight Floralozone.

[0259] As shown in Table 3, modified amino acid compounds provide benefits in detergent compositions. In this data set, Synthetic Examples 4 and 5 have improved benefits over Synthetic Example 3. The trimeric structure of Synthetic Example 4 produced the highest headspace. No clear trends are obtained between the individual benefit agents across the series tested.

[0260] Dimensions and values ​​disclosed herein should not be understood as being strictly limited to the exact numerical values ​​recited. Instead, unless otherwise indicated, each such dimension is intended to mean both the recited value and a functionally equivalent range surrounding that value. For example, a dimension disclosed as "40 mm" is intended to mean "about 40 mm."

[0261] All documents cited herein, including any cross-referenced or related patents or patent applications, and any patent applications or patents to which this application claims priority or benefit, are incorporated herein by reference in their entirety, unless expressly stated to the contrary. The citation of any document shall not be deemed to be prior art to any invention disclosed or claimed herein, or to teach, suggest, or disclose any such invention, either alone or in combination with any other reference or references. Furthermore, to the extent that any meaning or definition of a term in this document conflicts with any meaning or definition of the same term in a document incorporated by reference, the meaning or definition given to that term in this document shall govern.

[0262] While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.

Claims

1. 1. A treatment composition comprising: A processing aid; a modified amino acid multimer compound, said multimeric compound comprising a central linking group and 2 to 6 amino acid moieties each covalently bonded to said central linking group by a heteroatom selected from the group consisting of O, S and N, preferably O; the central linking group contains 3 to 18 carbon atoms; each amino acid moiety comprises a carbon backbone comprising one or more carbon atoms, a carbonyl group comprising a carbon atom, and a nitrogen atom; the heteroatom is directly bonded to the carbon atom of the carbonyl group and to the central linking group; at least one amino acid moiety comprises an organic moiety covalently bonded to the nitrogen atom of the amino acid moiety; said organic moiety comprising a benefit agent residue; Upon cleavage of one or more bonds connecting said beneficial agent residue to said amino acid moiety, the beneficial agent is released; A treatment composition, wherein the benefit agent comprises an aldehyde moiety, a ketone moiety, or a combination thereof.

2. 1. A treatment composition comprising: A processing aid; a modified amino acid multimer compound, the multimeric compound comprises a central linking group and 2 to 6 amino acid moieties each covalently bonded to the central linking group; the central linking group contains 3 to 18 carbon atoms; each amino acid moiety comprises a carbonyl group at its C-terminus, said carbonyl group comprising a carbon atom; the carbon atom of the carbonyl is bonded to a heteroatom of the central linking group; the heteroatom is selected from the group consisting of O, S, or N; each amino acid moiety further comprises a nitrogen atom at the N-terminus; at least one amino acid moiety comprises a benefit agent residue attached to said nitrogen atom at said N-terminus of said at least one amino acid moiety; Upon cleavage of one or more bonds connecting said beneficial agent residue to said amino acid moiety, the beneficial agent is released; A treatment composition, wherein the benefit agent comprises an aldehyde moiety, a ketone moiety, or a combination thereof.

3. 3. The treatment composition of claim 1 or 2, wherein the carbon backbone of each amino acid moiety independently comprises 1 to 9 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, more preferably 1 to 2 carbon atoms, even more preferably 1 carbon atom.

4. at least one, preferably at least two, more preferably all of said amino acid moieties are proteinogenic amino acids; Preferably, proteinogenic amino acids independently selected from cysteine, glycine, aspartic acid, glutamic acid, lysine, or combinations thereof; A treatment composition according to any one of claims 1 to 3, more preferably derived from cysteine.

5. The treatment composition according to any one of claims 1 to 4, wherein said amino acid moieties are derived from amino acids having the same identity, preferably from proteinogenic amino acids having the same identity.

6. A treatment composition according to any one of claims 1 to 5, wherein at least two, preferably all, of the amino acid moieties comprise a benefit agent residue.

7. 1. A treatment composition comprising: A processing aid; and a modified amino acid multimeric compound, the modified amino acid multimeric compound having Formula I: L[E] ｔ Formula I wherein t is independently an integer from 2 to 6, preferably from 2 to 5, more preferably from 2 to 4, more preferably from 2 to 3, more preferably 2; L is a central linking group that is polyvalent and contains 3 to 18 carbon atoms; each E group is independently selected from -GH, -GX, or a moiety according to formula II; 【Chemistry 1】 with the proviso that said multimeric compound comprises at least two E groups which are moieties according to formula II; ＊ indicates the point of attachment of said E group to L, the value of x is from 1 to 9, preferably from 1 to 6, more preferably from 1 to 3, even more preferably from 1 to 2, and even more preferably 1; Each G is independently -O-, -N(R ３ )-, or -S-; Preferably, each G group is the same; Each R ３ is, if present, independently selected from H or a monovalent moiety having a molecular weight of 14-881 Da, preferably 41-255 Da; X, if present, is a suitable charge balancing counterion; Each R １ is independently selected from H or a monovalent moiety having a molecular weight of 15 to 507 Da; Preferably, R １ is selected from the side groups of proteinogenic amino acids or monovalent moieties having a molecular weight of 15-142 Da, Each R ２ is independently selected from H and a monovalent moiety having a molecular weight of 15-1000 Da, preferably 15-507 Da, more preferably 15-142 Da; Preferably, R ２ is H, Each A group is a monovalent nitrogen-containing moiety, at least one A group comprises an independently selected benefit agent residue linked to the remainder of said A groups by one or more bonds, said one or more bonds being cleaved to release the benefit agent; The benefit agent comprises an aldehyde moiety, a ketone moiety, or a combination thereof. A treatment composition characterized by a structure according to

8. Each A group is independently (a)H ２ N-、 (b)Z ＊＊ N-、 (In the formula, ＊＊ represents a connecting bond between the nitrogen atom and a carbon atom of the Z group, said connecting bond being (i) a double bond, thereby forming an imine bond, or (ii) the benefit agent from which the benefit agent residue is derived comprises an α-β unsaturated carbonyl-containing moiety that is an aldehyde moiety or a ketone moiety; ＊＊ If the nitrogen atom of the N-group is further bonded to a hydrogen (-H), it is one of the single bonds formed from the 1,4-addition. (c) HG'(J) ｄ N(H)-, and (d) 【Chemistry 2】 wherein the subscript d is selected from 1 to 3, preferably d is 2 to 3, more preferably d is 2; Each G' is -O-, -S-, or -N(R ７ )-, preferably G is -O-, Each R ７ is, when present, independently selected from -H or a monovalent moiety having a molecular weight of about 15 to about 255 Da, preferably R ７ is a monovalent moiety having a molecular weight of from about 15 to about 142 Da, more preferably from about 15 to about 30 Da; the Z group contains 4 to 34 carbon atoms, and the N and the G' are attached to the same carbon atom of the Z group; Each J is independently C(R ９ ) ２ , —O— and —N(R ９ ), and preferably each J is selected from the group consisting of C(R ９ ) ２ and Each R ９ are independently selected from H or a monovalent moiety having a molecular weight between 14 and 990 Da, more preferably R ９ is selected from H or a monovalent moiety having a molecular weight between 14 and 186 Da, even more preferably R ９ is H, but However, the first R ９ and the second R ９ may be optionally taken together as a divalent substituent where possible, and preferably said divalent substituents are fused rings, spiro rings, and =N(R ７ ), ═O, and ═S; R ７ are as defined above, if present) is selected from the group consisting of At least one A group is independently selected from (b) or (d); More preferably, at least one A group is selected from the group consisting of (b) Z ＊＊ N-, Even more preferably, all A groups are (b) Z ＊＊ N-, 8. The treatment composition of claim 7, wherein each Z group is a residue of said independently selected benefit agent.

9. At least one A group is selected from the group consisting of (b) Z ＊＊ N-, Said Z ＊＊ The Z group of the N-moiety is 【Chemistry 3】 (Wherein, the =C(R ４ ) (R ５ ) and -CH(R ８ ) CH ２ C(O)R ５ each moiety represents a residue of a benefit agent, said residue of said benefit agent having said molecular formula that differs from the molecular formula of said benefit agent only by having one less O atom or one more H atom, said benefit agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof; Preferably, R ４ R is independently selected from monovalent organic moieties; ５ and R ８ is independently selected from the group consisting of hydrogen and monovalent organic moieties; More preferably, said benefit agent is a perfume raw material containing from 4 to 34 carbon atoms; However, R ４ and R ５ , or R ８ and R ５ may be linked to form a cyclic divalent organic moiety.

9. The treatment composition of claim 8, independently selected from the group consisting of:

10. The Z group has the following structure: 【Chemistry 4】 The treatment composition of any one of claims 7 to 9, wherein the benefit agent residue has the formula:

11. below: Two or more A groups comprise a benefit agent residue; For a given compound, the identities of the A groups are the same; For a given compound, the identities of the A groups vary. For a given compound, the identities of the Z groups are the same; and / or For a given compound, the identities of the Z groups vary. The treatment composition according to any one of claims 7 to 10, wherein at least one of the following is true:

12. At least one R ２ comprises a residue of an additional benefit agent, preferably said R ２ The treatment composition of any one of claims 7 to 11, wherein is a monovalent moiety having a molecular weight of from 54 to 1000 Da.

13. A treating composition according to any one of claims 1 to 12, wherein the central linking group comprises from 3 to 16 carbon atoms, preferably from 5 to 12 carbon atoms, more preferably from 8 to 12 carbon atoms.

14. The treatment composition of any one of claims 1 to 13, wherein the central linking group is a divalent, trivalent, or tetravalent organic moiety, preferably divalent.

15. the central linking group being a polyhydric alcohol, a polyhydric alcohol, preferably chosen from diols, triols or pentaerythritol, Even more preferably, the treatment composition according to any one of claims 1 to 14 is derived from a polyhydric alcohol selected from 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, glycerol, or pentaerythritol.

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