Pro-beneficial agent compound having a carbon / nitrogen bond

Abstract

Pro-benefit agent compounds comprising benefit agent fragments attached by carbon / nitrogen linkage bonds to a hydrophobically modified core, such as a hydrophobically modified amino acid, wherein the fragments are derived from benefit agents, such as perfume raw materials, that contain an aldehyde or ketone moiety, and related treatment compositions, premix compositions, and methods of making and using such compositions.

Description

Technical Field

[0001] The present disclosure relates to certain pro-beneficial agent compounds having carbon / nitrogen bonds, related treatment compositions, and methods of making and using such compositions. The pro-beneficial agent compounds may be derived from hydrophobic modified amino acids.

Background Art

[0002] Manufacturers of treatment compositions are constantly seeking ways to improve the delivery efficiency and / or performance benefits associated with certain beneficial agents. The use of pro-beneficial agent compounds, where the pro-beneficial agent fragment is linked to a carrier or precursor molecule by a cleavable or hydrolyzable bond and is then released when the bond is broken, can be a useful strategy. For example, certain amine compounds can form the basis of pro-fragrance or pro-perfume technologies. However, there is still room for improvement with respect to stability and / or deposition profiles.

[0003] Furthermore, consumers may desire materials related to a desirable environmental profile or sustainability profile.

Summary of the Invention

Problems to be Solved by the Invention

[0004] There is a need for pro-beneficial agent compounds that provide improved delivery, release, and / or stability profiles, as well as treatment compositions containing such compounds. There is also a need for methods of manufacturing and using such treatment compositions.

Means for Solving the Problems

[0005] The present disclosure relates to pro-beneficial agent compounds comprising a carbon-nitrogen bond and a hydrophobic moiety.

[0006] For example, the present disclosure relates to prodrug compounds, where the compound is a carbon-containing core comprising a carbon skeleton, one or more side groups, a nitrogen atom, and a carbonyl group, and the carbonyl group is part of a carbonyl-containing moiety selected from an ester moiety, an amide moiety, or a thioester moiety. The carbonyl-containing moiety contains a heteroatom bonded to the carbon of the carbonyl group, the heteroatom is selected from oxygen, nitrogen, or sulfur, the carbonyl-containing moiety further contains a hydrophobic moiety bonded to the heteroatom, and the hydrophobic moiety is an organic group containing 5 to 34 chain atoms, preferably carbon chain atoms. A prodrug fragment bonded to the core by a linking bond that is a single bond or a double bond, where the linking bond is between the nitrogen atom of the carbon-containing core and the carbon atom of the prodrug fragment. The single bond, if present, is formed by a 1,4-addition process, and the double bond, if present, is part of an imine bond. When the linking bond cleaves, the prodrug is released, and the prodrug contains a prodrug fragment that includes an aldehyde moiety, a ketone moiety, or a combination thereof. The prodrug compound is preferably derived from a hydrophobically modified amino acid.

[0007] The present disclosure also relates to a pro-beneficial agent compound comprising a carbon-containing core in which the compound comprises a carbon skeleton, one or more side groups, a nitrogen atom, and a carbonyl group, wherein the carbonyl group is part of a carbonyl-containing moiety in which the carbonyl group is an amide moiety, the carbonyl-containing moiety comprises a heteroatom bonded to the carbon of the carbonyl group, the heteroatom is nitrogen, the carbonyl-containing moiety further comprises one or two hydrophobic moieties bonded to the heteroatom, the one or two hydrophobic moieties are organic groups, the total number of chain atoms in the one or two hydrophobic moieties (e.g., the number of chain atoms in the first hydrophobic moiety plus the number of chain atoms in the second hydrophobic moiety if present) is from 5 to 34, preferably the chain atoms are carbon atoms or a mixture of carbon atoms and oxygen atoms forming at least one alkoxylate group, more preferably the chain atoms are carbon atoms; a beneficial agent fragment bonded to the core by a linking bond that is a single bond or a double bond, wherein the linking bond is between the nitrogen atom of the carbon-containing core and the carbon atom of the beneficial agent fragment, the single bond, if present, is formed by a 1,4-addition process, the double bond, if present, is part of an imine bond, and upon cleavage of the linking bond, the beneficial agent is released, and the beneficial agent comprises an aldehyde moiety, a ketone moiety, or a combination thereof; and the beneficial agent fragment.

[0008] The present disclosure also relates to a treatment composition comprising an auxiliary component and a pro-beneficial agent compound as described above.

[0009] The present disclosure also relates to a premix composition comprising a pro-beneficial agent compound, wherein the precursor compound comprises a carbon-containing core, the carbon-containing core comprises a carbon skeleton, one or more side groups, a nitrogen atom (preferably a primary amine group), and a carbonyl group, the carbonyl group is part of a carbonyl-containing moiety selected from an ester moiety, an amide moiety, or a thioester moiety, the carbonyl-containing moiety comprises a heteroatom bonded to the carbon of the carbonyl group, the heteroatom is selected from oxygen, nitrogen, or sulfur, the carbonyl-containing moiety further comprises a hydrophobic moiety bonded to the heteroatom, and the hydrophobic moiety is an organic group comprising 5 to 34 chain atoms, and a beneficial agent having an aldehyde moiety, a ketone moiety, or a combination thereof. The pro-beneficial agent precursor and the beneficial agent may optionally react to form a pro-beneficial agent compound as described above. In the premix composition, the total weight percentage of the pro-beneficial agent precursor, the beneficial agent, and, if present, the pro-beneficial agent compound may be from about 10 wt% to about 100 wt% of the premix composition.

[0010] The present disclosure relates to a method for manufacturing a treatment composition described herein. The method may comprise at least one of the following: (a) combining a pro-beneficial agent compound with an auxiliary component, preferably where the auxiliary component is part of a base composition; (b) combining the above premix composition with an auxiliary component, preferably where the auxiliary component is part of a base composition; (c) combining a pro-beneficial agent precursor compound, a beneficial agent, and an auxiliary component, preferably where the auxiliary component is part of a base composition and the pro-beneficial agent precursor compound and the beneficial agent are added to the base composition as separate inputs.

[0011] 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 further optionally comprising a rinsing and / or drying step. **DETAILED DESCRIPTION OF THE INVENTION**

[0012] The present disclosure relates to pro-beneficial agent compounds that can be derived from modified amino acids. The compounds may include fragments or residues of beneficial agents, such as fragrance ingredients or antibacterial agents, that contain an aldehyde or ketone moiety. In the pro-beneficial agent compounds of the present disclosure, the beneficial agent fragment or residue is attached to the nitrogen atom of the modified amino acid by a linking bond that is a carbon / nitrogen bond, such as a bond formed via an imine bond or a 1,4-addition process. Without being bound by theory, it is believed that when the linking bond is broken (e.g., by hydrolysis or back-reversion), the beneficial agent is released.

[0013] Furthermore, the modified amino acid includes an organic group attached to the acid terminus of the amino acid, thereby forming a carbonyl-containing group that can be selected from an ester group, an amide group, or a thioester group. The organic group may be selected to increase the overall hydrophobicity of the resulting compound, which is thought to improve the delivery and / or attachment of the pro-beneficial agent compound to the intended target surface or article.

[0014] Such pro-beneficial agent compounds, related treatment compositions, and related methods are described in more detail below.

[0015] As used herein, the articles “a” and “an” when used in the claims 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 non-limiting. The compositions of the present disclosure can comprise, consist essentially of, or consist of the components of the present disclosure.

[0016] In this specification, the terms "substantially free of" or "substantially free from" may be used. This means that the indicated material is present in minimal amounts and is not intentionally added to the composition to form part of the composition, or preferably, is not present at analytically detectable levels. It means that the composition includes the indicated material only as an impurity in one of the other materials that are intentionally included. The indicated material, if present, may be present at a level of less than 1% by weight, or less than 0.1% by weight, or less than 0.01% by weight, or even 0% by weight of the composition.

[0017] As used herein, the phrase "fabric care composition" includes compositions and formulations designed to treat fabrics. Such compositions include laundry washing compositions and detergents, fabric softening compositions, fabric strengthening compositions, fabric deodorizing compositions, pre-wash detergents, pre-wash treatment agents, laundry additives, spray products, dry cleaning agents or compositions, post-rinse additives for laundry, 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 apparent to those skilled in the art in view of the teachings herein, but are not limited thereto. Such compositions can be used as pre-wash treatment agents, post-wash treatment agents, or added during the rinse or wash cycle of a laundry operation.

[0018] As used herein, the phrase "chain atoms" means the sum of all atoms in the indicated group or moiety, excluding hydrogen atoms. The chain atoms may be in a linear arrangement, a branched arrangement, and / or a cyclic arrangement.

[0019] Unless otherwise noted, all levels of components or compositions are with respect to the active portion of such components or compositions, excluding impurities that may be present in commercial sources of such components or compositions, such as residual solvents or by-products.

[0020] All temperatures in this specification are in degrees Celsius (°C) unless otherwise indicated. Unless otherwise stated, all measurements in this specification are carried out at 20 °C and atmospheric pressure.

[0021] In all embodiments of the present disclosure, all percentages are by weight of the total composition unless otherwise specified. Unless otherwise indicated, all ratios are weight ratios.

[0022] It is to be understood that all upper numerical limits given throughout this specification include all lower numerical limits as if such lower numerical limits were expressly recited herein. All lower numerical limits shown throughout this specification include all higher numerical limitations as if such higher numerical limitations were expressly recited herein. All numerical ranges given throughout this specification include any narrower numerical ranges that fall within such broader numerical ranges as if such narrower numerical ranges were all expressly recited herein.

[0023] Pro-beneficial agent compound The present disclosure relates to pro-beneficial agent compounds. A pro-beneficial agent compound contains a fragment (e.g., a residue) of a beneficial agent. The beneficial agent contains an oxygen-containing moiety, i.e., an aldehyde moiety or a ketone moiety.

[0024] The beneficial agent fragment, which is preferably a first beneficial agent fragment, is bonded to a nitrogen atom of a carrier molecule (e.g., a precursor compound) by a carbon / nitrogen linking bond. The linking bond may be a single bond formed by a 1,4-addition process. The linking bond may be a double bond that is part of an imine bond. When the carbon / nitrogen bond is broken (e.g., by hydrolysis), the beneficial agent is released. The release of the beneficial agent may be caused by any suitable mechanism such as water or heat, preferably the presence of water, especially when the linking bond is an imine bond.

[0025] The beneficial agent compounds of the present disclosure may be derived from modified amino acids. Since protein - constituting amino acids tend to be naturally occurring, such compounds can be attractive starting materials for environmental or sustainability reasons and can be preferred starting materials. For most naturally occurring amino acids, the stereogenic carbon at the α - position relative to the amino group has the L - configuration. D - amino acids are occasionally found in nature. Either L - amino acids or D - amino acids, as well as mixtures, can be used, but due to economic factors, the more abundant L - amino acids may be preferred. In this context, biosynthetic amino acids may be preferred.

[0026] The starting amino acid can be hydrophobically modified by reacting the carboxylic acid group of the amino acid with (a) an alcohol of an organic group via an esterification reaction, (b) an amine of an organic group via an amidation reaction, or (c) a thiol group of an organic group via a thioesterification reaction. Such reactions can result in ester, amide, or thioester linking groups, respectively. Such linking groups, each of which is a type of carbonyl - containing partial group, may be preferred compared to others to facilitate the reaction. Compounds formed using such carbonyl - containing moieties may be more preferred for environmental reasons since these types of groups can decompose (e.g., hydrolyze) over time and / or in the presence of water, leaving the core material, for example, as a common amino acid.

[0027] The present disclosure relates to a pro-beneficial agent compound, the compound comprising a carbon-containing core comprising a carbon skeleton, one or more side groups, a nitrogen atom, and a carbonyl group, the carbonyl group being part of a carbonyl-containing moiety selected from an ester moiety, an amide moiety, or a thioester moiety, the carbonyl-containing moiety comprising a heteroatom bonded to the carbon of the carbonyl group, the heteroatom being selected from oxygen, nitrogen, or sulfur, the carbonyl-containing moiety further comprising a hydrophobic moiety bonded to the heteroatom, the hydrophobic moiety being an organic group comprising 5 to 34 chain atoms, a carbon-containing core, and a beneficial agent fragment bonded to the core by a linking bond that is a single bond or a double bond, the linking bond being located between the nitrogen atom of the carbon-containing core and the carbon atom of the beneficial agent fragment, the single bond, when present, being formed by a 1,4-addition process, the double bond, when present, being part of an imine bond, and when the linking bond cleaves (e.g., breaks, which can in some cases be by hydrolysis), the beneficial agent is released, the beneficial agent comprising a beneficial agent fragment comprising an aldehyde moiety, a ketone moiety, or a combination thereof.

[0028] The carbon-containing core comprises a carbon skeleton. The carbon skeleton is understood to not include the carbon of the carbonyl-containing moiety or side groups (if present). The carbon skeleton can comprise 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms, more preferably 1 carbon atom. For reasons of mass efficiency, relatively few carbon atoms may be preferred. In particular, a skeleton comprising only 1 carbon atom may be preferred as such structures are indicative of the proteinogenic amino acids that occur naturally.

[0029] The carbon-containing core can be derived from an amino acid. Preferably, the core is derived from a proteinogenic amino acid. 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.

[0030] At least one side group can be selected from hydrogen or a suitable organic group, preferably hydrogen or an organic group having 1 to about 20 chain atoms, preferably carbon atoms. At least one side group may contain one or more functional groups such as a carboxyl group, an amine group, a thiol group, or a hydroxyl group. At least one side group may be linear or branched. At least one side group may contain an aryl ring. The compound may preferably contain only one non-hydrogen side group (e.g., only one organic group). The compound may contain two or more non-hydrogen side groups. At least one side group preferably contains a side group of a protein constituent amino acid. The carbon-containing core may contain at least one side group that is hydrogen and at least one side group that is an organic group. For example, if the core is based on or derived from glycine, all side groups may be hydrogen.

[0031] The side group may have the structure of a side group of a protein constituent amino acid or its derivative, preferably selected from the group consisting of valine, phenylalanine, leucine, isoleucine, their derivatives, or combinations thereof, more preferably valine, phenylalanine, their derivatives, or combinations thereof. The derivative may include a substitution containing a beneficial agent fragment attached to the side group derivative.

[0032] At least one side group can include a member having a structure selected from the following group, where "#" represents the location where the side group is attached to a carbon atom of the carbon-containing core.

[0033] [Table 1]

[0034] When the carbon-containing core contains a side group having a structure that is a side group of a protein constituent acid, preferably a side group selected from the above table, the remaining side groups may preferably be hydrogen.

[0035] The carbon-containing core (e.g., the parent amino acid) may preferably contain a relatively hydrophobic side group, for example, one that does not contain a hydrophilic functional group such as a carboxy group. The relatively hydrophobic side group is thought to facilitate the attachment of the pro-benefit agent compound to the target surface, particularly when the compound is delivered in an aqueous solution such as a laundry detergent solution.

[0036] The protein constituent amino acids from which the carbon-containing core is derived may be selected from the group consisting of valine, phenylalanine, leucine, isoleucine, or combinations thereof, preferably valine, phenylalanine, or combinations thereof. Such pro-benefit agent compounds derived from these amino acids have been found to be particularly effective for delivering benefit agents, particularly fragrance ingredients, more specifically in laundry applications.

[0037] The pro-benefit agent compounds of the present disclosure include a hydrophobic moiety (which may also be simply referred to herein as a "hydrophobic substance"). As used in this context, "hydrophobic" means describing an organic group having a logP of at least 1.3, where logP is determined for the parent alcohol of the organic group, regardless of whether the organic group is derived from an alcohol, an amine, or a thiol. For example, if the hydrophobic moiety is a straight-chain group having 8 carbons and is bonded to the heteroatom of the carbonyl-containing moiety at the terminal position of the hydrophobic substance, logP is determined according to the logP value of 1-octanol (in this case, logP = about 3.0), regardless of whether the hydrophobic moiety is bonded to the core via an ester bond, an amide bond, or a thioester bond (see Table A below). The hydrophobic moiety (e.g., the Q group as described below) can be characterized by a logP of at least 1.3, or about 2.8 to about 10.8, or about 3.0 to about 7.8, or about 5.0 to about 6.9. The hydrophobic moiety (e.g., the parent alcohol of the hydrophobic moiety / Q) can preferably be characterized by a logP of about 1.6 to about 10, preferably about 2 to about 8, more preferably about 2.5 to about 8, and even more preferably about 2.5 to about 5.

[0038] The method for determining logP is found in the following test methods section.

[0039]

Table 2

[0040] As described above, the hydrophobic moiety can be attached to the carbon-containing core by a carbonyl-containing moiety selected from an ester moiety, an amide moiety, or a thioester moiety. Such a carbonyl-containing moiety can be formed by reacting the carboxylic acid terminus of the core amino acid with an appropriate functional group (e.g., alcohol, amine, or thiol) of an appropriate (hydrophobic) organic group. The carbonyl-containing moiety that attaches the hydrophobic moiety to the core may preferably be an ester moiety, for example, due to the low cost of the alcohol precursor or the favorable environmental profile of the resulting ester.

[0041] As described above, the hydrophobic moiety may be an organic group containing 5 to 34 chain atoms, preferably carbon atoms. Without being bound by theory, a specific minimum value of chain atoms is useful for increasing the relative hydrophobicity of the group and thus the resulting compound, which in turn may help facilitate deposition or increased performance. The hydrophobic moiety may be an organic group containing from about 8 to about 18 chain atoms, more preferably from about 8 to about 14 chain atoms, and even more preferably, most or all of the chain atoms are carbon atoms. The chain atoms may preferably be carbon atoms or a mixture of carbon and oxygen atoms that form at least one alkoxylate group.

[0042] The carbonyl-containing moiety may preferably be an amide moiety. The amide moiety may be preferred for reasons of stability and / or when the beneficial agent fragment is a fragment of an antibacterial agent. In such cases, the compound may have one or two hydrophobic moieties that are part of the carbonyl-containing moiety. Without being bound by theory, it is thought that two hydrophobic moieties, even if relatively small, can provide an appropriate degree of hydrophobicity such that the compound functions in a similar manner to when it has one larger hydrophobic substance.

[0043] For example, the present disclosure provides a carbon-containing core that includes a carbon skeleton, one or more side groups, a nitrogen atom, and a carbonyl group, where the carbonyl group is part of a carbonyl-containing moiety that is an amide moiety, the carbonyl-containing moiety includes a heteroatom bonded to the carbon of the carbonyl group, the heteroatom is nitrogen, the carbonyl-containing moiety further includes one or two hydrophobic moieties bonded to the heteroatom, the one or two hydrophobic moieties are organic groups, the total number of chain atoms in the one or two hydrophobic moieties (e.g., the number of chain atoms in the first hydrophobic moiety plus the number of chain atoms in the second hydrophobic moiety if present) is from 5 to 34, preferably the chain atoms are carbon atoms that form at least one alkoxylate group or a mixture of carbon and oxygen atoms, more preferably the chain atoms are carbon atoms, a carbon-containing core, and a beneficial agent fragment bonded to the core by a linking bond that is a single bond or a double bond, where the linking bond is between a nitrogen atom of the carbon-containing core and a carbon atom of the beneficial agent fragment, the single bond, if present, is formed by a 1,4-addition process, the double bond, if present, is part of an imine bond, and when the linking bond cleaves, the beneficial agent is released, and the beneficial agent includes an aldehyde moiety, a ketone moiety, or a combination thereof, a beneficial agent fragment, and a pro-beneficial agent compound. The total number of chain atoms in the one or two hydrophobic moieties may be from about 8 to about 18 chain atoms, preferably from about 8 to about 14 chain atoms. The carbonyl-containing moiety can include two hydrophobic moieties bonded to the heteroatom, which may be preferred for reasons of stability. At least one of the two hydrophobic moieties bonded to the heteroatom includes at least 3, preferably at least 4 chain atoms. Each of the two hydrophobic moieties bonded to the heteroatom independently includes at least 2, preferably at least 3, preferably at least 4 chain atoms. The one or two hydrophobic moieties may independently be an unsubstituted organic group, an unbranched organic group, or a combination thereof, preferably a combination thereof.

[0044] When the beneficial agent fragment is derived from a fragrance raw material, a relatively high hydrophobicity may be preferred for reasons of adhesion or performance. For example, when the beneficial agent to be released is a fragrance raw material, the organic group may contain about 8 to about 18, preferably about 10 to about 18, more preferably about 12 to about 18, and even more preferably about 12 to about 16 chain atoms, and preferably most or even all of the chain atoms are carbon atoms.

[0045] When the beneficial agent fragment is derived from an antibacterial agent, a relatively low hydrophobicity may be preferred for performance reasons. For example, when the beneficial agent to be released is an antibacterial agent, the organic group may contain about 6 to about 14, preferably about 6 to about 12, preferably about 8 to about 12, and more preferably about 8 to about 10 chain atoms, and preferably the chain atoms are carbon atoms. In such cases, it may be particularly preferred that the hydrophobic moiety is connected via an amide bond.

[0046] The hydrophobic moiety may be optionally substituted, but such substitutions are preferably selected to maintain the hydrophobicity of the organic group. For example, the organic group may contain relatively hydrophobic substitutions. Additionally or alternatively, the organic group may contain hydrophilic substitutions, but they are preferably kept to a minimum and / or the number of chain atoms is appropriately selected to offset part of the hydrophilicity of the substitution. For example, when the organic group contains a hydroxyl substitution, it may be preferred that the organic group contains at least 10, preferably at least 12 carbon atoms.

[0047] The hydrophobic moiety may be an unsubstituted organic group, an unbranched organic group, or a combination thereof. Preferably, the hydrophobic moiety is both unsubstituted and unbranched. Such moieties may be preferred due to convenient availability, performance profiles, and relatively low environmental impact. Suitable moieties may be derived from n-octanol, n-decanol, n-dodecanol, etc.

[0048] The hydrophobic moiety may be derived from a mixture of feedstock materials such as fatty alcohols. The feedstock materials may include materials having a variable chain length. In such cases, the chain length described herein for the hydrophobic moiety is understood to be the weight average chain length.

[0049] Additionally or alternatively, the feedstock materials used to form the hydrophobic moiety may include some linear and some branched materials. Thus, when reacting the feedstock to form a precursor or pro-beneficial agent compound of the present disclosure, some materials include linear monovalent moieties and other materials include branched monovalent moieties. Such mixtures are contemplated in the present disclosure.

[0050] The hydrophobic moiety may include a second fragment of a second beneficial agent, which may be released ultimately from the pro-beneficial agent compound in addition to the beneficial agent bound to the core nitrogen atom, which may be referred to as the first beneficial agent. Such a configuration may be preferred for reasons of loading efficiency. The two fragments may be bound to and released from the compound. Such a configuration may also be preferred to enable different beneficial agents to be released from the same compound.

[0051] For example, the second beneficial agent fragment may have a different identity from the beneficial agent fragment bound to the core nitrogen. Both fragments may be beneficial agents of the same category (e.g., both derived from fragrance ingredients), but they may have different identities. Preferably, the first and second beneficial agents include different functional groups. For example, the first beneficial agent may include an aldehyde or ketone moiety, and the second beneficial agent may include a functional group that is not an aldehyde or ketone moiety. The second beneficial agent may include a functional group that is an alcohol, amine, thiol, or a combination thereof.

[0052] Preferably, the second beneficial agent contains a functional group that is an alcohol group. Such alcohol-containing materials may be preferred to facilitate the reaction with the carboxylic acid of the amino acid core (e.g., thereby forming an ester). Such materials may also be preferred to provide a broader spectrum of materials released from the pro-beneficial agent compound (e.g., an aldehyde- or ketone-containing beneficial agent combined with an alcohol-containing beneficial agent).

[0053] The hydrophobic moiety may be substituted with a fragment of the second beneficial agent. The hydrophobic moiety may be (in its entirety) a fragment of the second beneficial agent.

[0054] The second beneficial agent may be a fragrance raw material, preferably an alcohol-containing fragrance raw material. In such a case, it is also preferred that the first beneficial agent (e.g., the parent material of the fragment attached to the nitrogen atom of the core) is also a fragrance raw material, which enables more efficient fragrance delivery and / or a more complex olfactory experience.

[0055] For environmental reasons, especially when the carbon-containing core is derived from a naturally occurring amino acid, it may be preferred that the hydrophobic moiety is derived from a natural material or feedstock. Suitable natural materials or feedstocks can include natural fats and / or oils.

[0056] The hydrophobic moiety may be a monovalent moiety, e.g., a monovalent organic group. For reasons of ease of reaction and / or processing, a monovalent hydrophobic moiety may be preferred. In such a case, the hydrophobic moiety is bonded to a heteroatom, which in turn is effectively bonded to the carbon of the carbonyl group of the carbon-containing core (e.g., an amino acid derivative) at the terminal or capping position.

[0057] As described in more detail below as Formula I, such compounds may take the form of "Z ** A-Q", where Z is a beneficial agent fragment, A is a carbon-containing core (e.g., a parent amino acid), and Q is a hydrophobic moiety, e.g., a monovalent organic group.

[0058] The prodrug compound can be characterized by a structure according to Formula I.

[0059] Z ** A-Q Formula I Wherein Z is a beneficial agent fragment, preferably a first beneficial agent fragment, wherein A represents a carbon-containing core, and wherein ** represents a linking bond between the nitrogen atom of the A group and the carbon atom of the Z group, and the linking bond is either (a) a double bond, thereby forming an imine bond, or (b) when the beneficial agent from which the beneficial agent fragment is derived contains an alpha-beta unsaturated carbonyl-containing moiety that is an aldehyde moiety or a ketone moiety, a single bond formed from a 1,4-addition, and wherein Q is a hydrophobic moiety, such as a monovalent organic group.

[0060] The prodrug compound can be characterized by a structure according to Formula II.

[0061]

Chemical formula

[0062] In Formula II, G may be selected from -O-, -S-, or -N(R 3 )-, preferably G is -O-. The ester obtained when G is -O may be preferred for environmental reasons and for the convenient availability of alcohol-based feedstock materials. For clarity, the -C(O)G moiety of Formula II represents the carbonyl-containing moiety of the carbon-containing core bonded to the hydrophobic substance (Q).

[0063] In Formula II, G may be selected from -N(R 3 -, where R 3 is selected from -H or a monovalent moiety having a molecular weight of about 15 to about 142 Da, preferably, R 3 is selected from -H or a monovalent moiety having a molecular weight of about 15 to about 30 Da, and more preferably, R 3 is -H. A relatively small R 3 moiety, especially hydrogen, may be preferred, for example, for favorable reactions and the availability of feedstock materials, when forming an amide bond. Amides can be formed, for example, from protected or unprotected amino acids. When protected, inorganic and organic acids may be most preferred. For unprotected amino acids, group III elements, chelating catalysts from group IV elements, and transition metal catalysts may be preferred. Catalysts containing elements of B, Si, and Ti are even more preferred.

[0064] The pro-beneficial agent compound may preferably be characterized by the structure according to Formula II, where G is -NR 3- , where R 3 is selected from -H or a monovalent moiety having a molecular weight of about 15 to about 142 Da, preferably where R 3 is a monovalent moiety having a molecular weight of about 15 to about 142 Da, and more preferably a monovalent moiety having a molecular weight of about 15 to about 30 Da. In the formula, Q and R 3When present, together they contain a total of 5 to 34 chain atoms, preferably about 8 to about 18 chain atoms, more preferably about 8 to about 14 chain atoms.

[0065] In Formula I or II, Q can contain 5 to 34 chain atoms, preferably about 8 to about 18 chain atoms, more preferably about 8 to about 14 chain atoms, and most preferably the chain atoms are carbon atoms. As described above, such hydrophobic moieties are preferred for reasons of efficient deposition and performance advantages. The Q group can be unsubstituted, unbranched, or a combination thereof, preferably a combination thereof.

[0066] The Q group can contain a second beneficial agent, preferably a second fragrance ingredient, more preferably a second fragment of an alcohol-containing second fragrance ingredient. In such a case, G can be -O-. When such materials are present, other materials containing a carbon-containing core and a hydrophobic moiety but not containing a first beneficial agent fragment bonded to the nitrogen of the carbon-containing core may also be present.

[0067] In Formula II, R 1 and R 2 can be independently selected from -H or a monovalent moiety having a molecular weight of about 15 to about 1000 Da, preferably from -H or a monovalent moiety having a molecular weight of about 15 to about 507 Da, more preferably from -H or a monovalent moiety having a molecular weight of about 15 to about 142 Da. R 1 and / or R 2 are side groups of the carbon-containing core. At least one of R 1 and R 2 , preferably at least one R 1 is preferably a monovalent moiety that is a side chain of a proteinogenic amino acid when R 2 is hydrogen (-H) and m = 1. At least one of R 1 and R 2 can contain a beneficial agent fragment. Such a configuration may be preferred for reasons of mass efficiency in that one carrier contains two fragments (one on the side chain and one on the amine group).

[0068] In Formula I or II, ** represents a bond between the nitrogen atom of the core (e.g., A group) and the carbon atom of the Z group. ** The bond may be a double bond, thereby forming an imine bond (e.g., C=N-). ** The bond may be a single bond formed from a 1,4-addition when the beneficial agent from which the beneficial agent fragment is derived contains an α-β unsaturated carbonyl that is an aldehyde moiety or a ketone moiety. Preferably, the 1,4-addition is a Michael-type addition. ** When represents a single bond, the nitrogen atom may further be bonded to a hydrogen (-H) (e.g., C-NH-).

[0069] In Formula II, the subscript m is from 1 to 6, preferably m is from 1 to 3, and more preferably, m is 1. When m is 1, the carbon-containing core may be a naturally occurring or biosynthetic proteinogenic amino acid, which may be preferred for environmental reasons.

[0070] In Formula I or II, ** the Z group is a group in which the beneficial agent fragment (Z) is bonded to the nitrogen atom of the carbon-containing core by a linking bond ( ** ). As described above, ** the linking bond may be a single bond or a double bond. Preferably, the Z moiety contains from about 4 to about 34 carbon atoms. The Z moiety is preferably a fragment of a fragrance raw material. The beneficial agent and its fragments are discussed in more detail below.

[0071] ** When the linking bond is a double bond (e.g., forming an imine bond), the Z group may be represented by the following structure.

[0072]

Chemical Formula

[0073] ** When the linking bond is a single bond, the Z group can be represented by the following structure.

[0074]

Chemical formula

[0075] In formula I, the A group may be characterized by the following structure, formula III.

[0076] [Chemical formula] In the formula, R 1 , R 2 , G, and m are defined as above, # represents the bonding point of G to the hydrophobic moiety Q, ** represents the bonding point to Z and can be a single bond (in this case, with -H also bonded to the nitrogen atom) or a double bond (forming an imine bond with the beneficial agent fragment Z).

[0077] The pro-beneficial agent compound may be characterized by the structure according to formula II, where m = 1, and R 1 is the side group of a protein constituent amino acid, and R 2 is -H. This embodiment may be preferred because it can be based on a naturally occurring amino acid core. In such a case, G = -O- may be more preferred because the resulting ester may be preferred for environmental reasons.

[0078] The pro-beneficial agent compound is preferably represented by formula II, where G = -O-. m ≥ 1, and R 1 is the side group of a protein constituent amino acid, R 2 is H, Z is a fragment of a fragrance raw material, and Q is an organic group containing about 8 to about 18 chain atoms, preferably the chain atoms are carbon atoms. With such a configuration, the pro-beneficial agent compound is considered to provide advantageous performance benefits and have a beneficial environmental profile.

[0079] The pro-beneficial agent compound may preferably be of the type according to formula II, where G = -N(R 3 )-, m ≥ 1, R 1 is the side group of a protein constituent amino acid, R 2 is H, Z is a fragment of a fragrance raw material, Q is an organic group containing about 1 to about 18 chain atoms, preferably the chain atoms are carbon atoms, and R 3 is an organic group containing about 1 to about 16 chain atoms, preferably the chain atoms are carbon atoms. In the formula, Q and R 3The total number of chain atoms therein is from 5 to 34.

[0080] The pro-beneficial agent compound may preferably be of formula II, wherein G = -N(R 3 )-, m ≧ 1, R 1 is the side group of a proteinogenic amino acid, R 2 is H, Z is a fragment of an antibacterial agent, Q is an organic group containing from about 1 to about 18 chain atoms, preferably the chain atoms are carbon atoms, and R 3 is an organic group containing from about 1 to about 16 chain atoms, preferably the chain atoms are carbon atoms, wherein the total number of chain atoms in Q and R 3 is from 5 to 34.

[0081] Beneficial agents and fragments thereof The pro-beneficial agent compounds of the present disclosure include beneficial agent fragments derived from aldehyde-containing beneficial agents, ketone-containing beneficial agents, or combinations thereof. The beneficial agent fragments may be derived from beneficial agents containing an aldehyde moiety. The beneficial agent fragments may be derived from beneficial agents containing a ketone moiety. The beneficial agent may contain an α-β unsaturated carbonyl group that is an aldehyde or ketone moiety.

[0082] As used herein, the beneficial agent from which a beneficial agent fragment is derived may be referred to as the parent beneficial agent.

[0083] The aldehyde or ketone moiety of the parent beneficial agent may react with the nitrogen atom of the core of the compound (e.g., the nitrogen of an amino acid) to result in a beneficial agent fragment bonded to the core at the nitrogen atom. As described above, this may be via a double bond that is an imine bond, or a single bond that may be a linking bond formed via a 1,4-addition process such as a 1,4-Michael type addition. When the linking bond connecting the beneficial agent fragment to the nitrogen atom is formed via 1,4-addition, the parent beneficial agent may contain an alpha-beta unsaturated carbonyl, and the carbonyl is an aldehyde moiety or a ketone moiety.

[0084] For example, when the linking bond is broken by hydrolysis, a beneficial agent is released. The linking bond can be broken by inducing conditions such as the presence of water or an increase in temperature.

[0085] The beneficial agent fragment can be derived from any suitable beneficial agent that can include a fragrance raw material, an antibacterial agent, an insecticide, an insect repellent, an antifungal agent, a herbicide, a hue dye, an antioxidant, a non-fragrance sensory stimulant, or a combination thereof, preferably a fragrance raw material, an antibacterial agent, or a combination thereof, more preferably a fragrance raw material. Some of these beneficial agents are described in more detail below.

[0086] Fragrance raw material The beneficial agent may be a fragrance raw material ( "PRM") that includes an aldehyde moiety, a ketone moiety, or a mixture thereof. The beneficial agent fragment (e.g., the Z group) may be derived from the fragrance raw material.

[0087] As used herein, the term "fragrance raw material (or "PRM")" refers to a compound that can 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 in imparting an odor, aroma, essence, or fragrance, either alone or in combination with other fragrance raw materials. A list of common PRMs can be found in various references 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, P.M. and Lamparsky, D., Blackie Academic and Professional (1994).

[0088] Fragrance raw materials containing an aldehyde moiety are provided in Table B below. The materials provided in Table B are considered to be exemplary (but non-limiting) examples of PRMs suitable for use according to the present disclosure.

[0089]

Table 3-1

[0090]

Table 3-2

[0091] The flavoring raw material forming the beneficial agent fragment may be selected from the group consisting of the aldehyde-containing PRMs in Table A above. The PRM forming the PRM fragment may contain an aldehyde moiety, and preferably, methyl nonyl acetaldehyde, benzaldehyde, floralozone, isocyclocitral, triplal (ligustral), presilkeemon B, lilial, decyl aldehyde, undecylenic aldehyde, cyclamen homologue aldehyde, cyclamen aldehyde, Dupical, oncidal, adoxal, melonal, calypsone, anisaldehyde, heliotropin, cumin aldehyde, scentenal, 3,6-dimethylcyclohex-3-ene-1-carbaldehyde, satenal, 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, butyl cinnamic aldehyde, limoneral, amyl cinnamic aldehyde, hexyl cinnamic aldehyde, citronellal, citral, cis-3-hexen-1-al, and mixtures thereof.

[0092] As described above, the pro-beneficial agent compound may contain a fragment of a flavoring raw material containing a ketone moiety. The flavoring raw materials containing a ketone moiety are provided in Table C below. The materials provided in Table C are considered to be exemplary (but non-limiting) examples of PRMs suitable for use according to the present disclosure.

[0093]

Table 4-1

[0094]

Table 4-2

[0095] The flavor raw material forming the PRM fragment may be selected from the group consisting of the ketone-containing PRMs in Table C above. The PRM forming the PRM fragment may contain a ketone moiety, and preferably, is selected from the group consisting of neroliol, 4-(4-methoxyphenyl)butan-2-one, 1-naphthalen-2-ylethanone, nectaryl, trimofix O, floramone, delta-damascone, β-damascone, α-damascone, methyl ionone, 2-hexylcyclopenta-2-en-1-one, galbascone, and mixtures thereof.

[0096] Beneficial agent fragments can be derived from beneficial agents that are fragrance raw materials, preferably selected from the group consisting of methyl nonyl acetaldehyde, benzaldehyde, floralozone, isocyclocitral, triplal (ligustral), presilkeemon B, lilial, decyl aldehyde, undecylenic aldehyde, cyclamen homologue aldehyde, cyclamen aldehyde, Dupical, oncidar, adoxal, melonal, calypsone, anisaldehyde, heliotropin, cumin aldehyde scentenal, 3,6-dimethylcyclohex-3-ene-1-carbaldehyde, satenal, 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, butyl cinnamaldehyde, limoneral, amyl cinnamaldehyde, hexyl cinnamaldehyde, citronellal, citral, cis-3-hexen-1-al, nerylione, 4-(4-methoxyphenyl)butan-2-one, 1-naphthalen-2-ylethanone, nectaryl, trimofix O, fluramon, delta-damascon, beta-damascon, alpha-damascon, methyl ionone, 2-hexylcyclopent-2-en-1-one, galvascon, and mixtures thereof.

[0097] When the beneficial agent fragment is derived from a fragrance raw material, preferably a PRM listed in the previous paragraph, the hydrophobic moiety may preferably be an organic group containing from about 8 to about 18 chain atoms, more preferably from about 10 to about 18 chain atoms, and preferably the chain atoms are carbon atoms. Such a chain length is considered to provide a suitable degree of hydrophobicity to promote the adhesion effect, especially in washing applications where the pro-beneficial agent compound is used in an aqueous liquid.

[0098] The flavoring ingredients described 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.

[0099] B. Antibacterial agent The beneficial agent may be an antibacterial agent containing an aldehyde moiety, a ketone moiety, or a mixture thereof.

[0100] Examples of antibacterial agents suitable for use in the present pro-beneficial agent compound include acetylacetone enolate, gossypol, nootkatone, or a mixture thereof.

[0101] When the beneficial agent fragment is derived from an antibacterial agent, preferably the antibacterial agent listed in the previous paragraph, the hydrophobic moiety may preferably be an organic group containing about 6 to about 12 chain atoms, preferably the chain atoms are carbon atoms. Such a chain length is considered to provide a suitable degree of hydrophobicity to promote the antibacterial effect and to promote the desired interaction between the antibacterial agent and the target microorganism.

[0102] Method for producing pro-beneficial agent compounds and related precursor compounds The pro-beneficial agent compounds according to the present disclosure can be prepared by reacting a pro-beneficial agent precursor compound with a beneficial agent. Accordingly, the present disclosure relates to a method for producing pro-beneficial agent compounds.

[0103] A pro-beneficial agent precursor compound (or, as used herein, simply a "precursor compound") may include a carbon-containing core, which may include a carbon skeleton, one or more side groups, a nitrogen atom (preferably a nitrogen atom that is part of a primary amine group, -NH2), and a carbonyl group, where the carbonyl group is part of a carbonyl-containing moiety selected from an ester moiety, an amide moiety, or a thioester moiety, the carbonyl-containing moiety includes a heteroatom bonded to the carbon of the carbonyl group, the heteroatom is selected from oxygen, nitrogen, or sulfur, the carbonyl-containing moiety further includes a hydrophobic moiety bonded to the heteroatom, and the hydrophobic moiety is an organic group containing 5 to 34 chain atoms.

[0104] In fact, the precursor compound may be a pro-beneficial agent compound prior to reaction with the beneficial agent, in which case the nitrogen atom is in the primary amine (-NH2) form. The core, side groups, carbonyl-containing moiety, and hydrophobic moiety are preferably as described above.

[0105] The pro-beneficial agent precursor compound may be characterized by a structure according to Formula IV. H2-A-Q Formula IV Wherein two hydrogen atoms are each bonded to the nitrogen atom of group A, and A and Q are substantially as described above.

[0106] The pro-beneficial agent precursor compound may be characterized by a structure according to Formula V.

[0107]

Chemical formula

[0108] The pro-beneficial agent precursor compound may be prepared by reacting the carboxyl group of an amino acid with a compound according to the following formula H-G-Q, for example, by an esterification, amidation, or thioesterification reaction.

[0109] Premix The present disclosure further relates to specific premix compositions and methods for making such compositions. The premix can be conveniently prepared prior to product formulation, prepared at one manufacturing site, and even transported to another manufacturing site for product formulation.

[0110] The premix composition may include a pro-beneficial agent precursor compound (the precursor compound being as described above) and a beneficial agent (the beneficial agent being as described above). The preferences described above regarding the pro-beneficial agent compound, its components, and / or its precursors apply equally here.

[0111] For example, the premix composition may include a pro-beneficial agent precursor compound in which the precursor compound includes a carbon-containing core, the core includes side groups and an amine group, and a hydrophobic moiety bonded to the core by a carbonyl moiety, the carbonyl moiety being selected from an ester moiety, an amide moiety, or a thioester moiety, and a beneficial agent including an aldehyde moiety, a ketone moiety, or a combination thereof.

[0112] For reasons of loading efficiency, it is preferable to rationally match the molar amount of the beneficial agent, preferably the first beneficial agent, with the molar amount of the carrier molecule (here, the pro-beneficial agent precursor compound) described above. For example, the premix composition may include the pro-beneficial agent precursor compound and the beneficial agent 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.

[0113] Even more specifically, for reasons of loading efficiency, it is preferable to rationally match the molar amount of the beneficial agent, preferably the first beneficial agent, with the molar equivalent of the reactive functional group (e.g., preferably an amine group) of the above-mentioned carrier molecule (here, the pro-beneficial agent precursor compound). For example, the premix composition may contain the pro-beneficial agent precursor compound and the reactive functional group (e.g., preferably an amine group) of the beneficial agent 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. When the pro-beneficial agent precursor compound contains a plurality of binding points or a plurality of functional groups capable of forming such binding points with respect to the beneficial agent and optionally the second beneficial agent, the premix composition may contain such functional groups of the pro-beneficial agent precursor compound and the beneficial agent (plus, optionally, the second beneficial agent that can also bind to the precursor compound) 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.

[0114] The premix composition may be in the form of a neat fluid and may contain little or no water. In such cases, it may be desirable to include a water scavenger such as magnesium sulfate in the premix and / or physically remove water via molecular sieves or in a vacuum, etc. The premix composition may contain less than about 10% by weight, preferably less than about 5% by weight, more preferably less than about 1% by weight, and even more preferably less than about 0.1% by weight of water. A low-moisture premix composition may be particularly preferred when it is intended to be formulated into a low-moisture product composition such as a solid like a pastille or a compact formulation such as a unit-dose composition encapsulated in a water-soluble film. When the premix is a low-moisture premix, the premix may contain from about 1% to about 100% by weight, preferably from about 5% to about 100% by weight, more preferably from about 20% to about 100% by weight of the pro-beneficial agent compound. When the premix is a low-moisture premix, the premix may contain from about 0.01% to about 80% by weight, preferably from about 0.01% to about 20% by weight of the pro-beneficial promoter precursor compound. When the premix is a low-moisture premix, the premix may contain from about 0.01% to about 80% by weight, preferably from about 0.01% to about 20% by weight of the beneficial agent.

[0115] The premix composition may contain 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 contains water, the water may be present at a concentration of from about 50% to about 95% by weight, preferably from about 60% to about 90% by weight of the premix composition. When the premix contains water, the pro-beneficial promoter precursor compound may be added at a concentration of from about 0.01% to about 7.5% by weight of the premix composition. When the premix contains water, the beneficial agent may be added at a concentration of from about 0.01% to about 7.5% by weight of the premix composition.

[0116] In a premix composition, the precursor compound and the beneficial agent may react as described above to form a pro-beneficial agent compound. The precursor compound, the beneficial agent, and the pro-beneficial agent compound may all be present in equilibrium. Since the formation of the pro-beneficial agent compound containing an imine produces water by a condensation process, the equilibrium may shift towards the reactant side of the reaction (e.g., the precursor compound and the beneficial agent) if the premix contains water. Conversely, if the premix is substantially free of intentionally added water, a relatively large amount of the pro-beneficial agent compound may be present, but it is recognized that some water is formed as a result of the condensation reaction. When the formation of the pro-beneficial agent compound involves 1,4-addition, the equilibrium is thought to depend not on water but rather on the balance between the entropy contribution and the enthalpy contribution.

[0117] The total weight percentage of the pro-beneficial agent precursor, the beneficial agent, and, if present, the pro-beneficial agent compound may be from about 10 wt% to about 100 wt%, preferably from about 25 wt% to about 100 wt%, preferably from about 50 wt% to about 100 wt%, more preferably from about 75 wt% to about 100 wt% of the premix composition.

[0118] The 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 the pro-beneficial agent 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 the beneficial agent, and the resulting mixture is understood to constitute 100 parts by weight in total.

[0119] The premix composition may contain a plurality of precursors, a plurality of beneficial agents, and / or a plurality of pro-beneficial agent compounds. The premix composition may further contain additional agents that do not react to form the pro-beneficial agent compounds according to the present disclosure. For example, the premix composition may contain additional PR M, surfactants, solvents, or other processing aids or stabilizing aids.

[0120] The premix composition may contain a surfactant, preferably a nonionic surfactant. The surfactant can be useful for the stability of the premix composition and / or the emulsification process.

[0121] The present disclosure further relates to a method for preparing such a premix composition. The method may include combining a pro-beneficial agent precursor (e.g., according to Formula IV or V above) described herein with a beneficial agent described herein, wherein the beneficial agent contains an aldehyde moiety, a ketone moiety, or a combination thereof. The materials may be combined in the proportions provided above. The method may include removing free water or otherwise binding it, which can help promote the reaction in the premix towards the product (e.g., the pro-beneficial agent compound). If the premix composition contains water, the precursor compound and water may preferably be combined before the beneficial agent is added. Alternatively, the beneficial agent and water may be mixed before the beneficial agent is added.

[0122] Treatment composition The present composition relates to a treatment composition containing an auxiliary component and a pro-beneficial agent compound as described above.

[0123] The treatment composition may be a consumer product composition. The consumer product compositions of the present disclosure may be useful in baby care, beauty care, fabric care, home care, family care, feminine care, and / or healthcare applications. The treatment composition may be useful for treating surfaces such as fabrics, 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.

[0124] 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 combination thereof.

[0125] The treatment composition may be a fabric care composition such as a laundry detergent composition (including a heavy-duty liquid detergent or unit-dose article), a fabric conditioning composition (including a liquid fabric softening composition and / or a fabric strengthening composition), a laundry additive, a fabric pretreatment composition (including a spray, a pourable liquid, or a spray), a fabric refresher composition (including a spray), or a mixture thereof.

[0126] The treatment composition may be a beauty care composition, for example, a hair treatment product (including a shampoo and / or a conditioner), a skin care product (including a cream, a lotion, or other topically applicable products for consumer use), a shaving care product (including a shaving lotion, a foam, or a pre- or post-shave treatment), a personal cleansing product (including a liquid body wash, a liquid hand soap, and / or a bar soap), a deodorant and / or an antiperspirant, or a mixture thereof.

[0127] 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 for consumers or businesses.

[0128] 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 soluble sheet, a pastille or bead, a fibrous article, a tablet, a stick, a bar, a flake, a foam / mousse, a non-woven sheet, or a mixture thereof.

[0129] The treatment composition may be in liquid form. The liquid composition may contain from about 30% to, or from about 40% to, or from about 50% to, up to about 99% by weight, or up to about 95% by weight, or up to about 90% by weight, or up to about 75% by weight, or up to about 70% by weight, or up to about 60% by weight of water of the composition. The liquid composition may be a liquid laundry detergent, a liquid fabric softener, a liquid dishwashing detergent, a hair shampoo, a hair conditioner, or a mixture thereof.

[0130] The treatment composition may be in solid form. The solid composition may be a powdery or granular composition. Such a composition may be agglomerated or spray-dried. Such a composition may comprise a plurality of granules or particles, at least some of which may comprise different compositions. The composition may be a powdery or granular cleaning composition that may contain a bleaching agent. The composition may be in the form of beads or pastilles, which may be formed into tablets from a liquid melt. The composition may be an extruded product.

[0131] The treatment composition may be in particulate form such as a plurality of fine particles. Each individual fine particle may have a mass of from 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 polyoxalkylene, 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 particulate form, it may comprise from about 25% to about 99.99% by weight of a water-soluble carrier and from about 0.001% to about 50% by weight of a pro-beneficial agent compound. The particulate form may be in the form of beads or pastilles.

[0132] The treatment composition may be in the form of a single-use article such as a tablet, pouch, sheet, or fibrous article. Such a pouch typically includes a water-soluble film that at least partially encloses the composition, such as a polyvinyl alcohol water-soluble film. Suitable films are available from MonoSol, LLC (Indiana, USA). The composition can be enclosed in a single-compartment pouch or a multi-compartment pouch. The multi-compartment pouch may have at least two, at least three, or at least four compartments. The multi-compartment pouch may include compartments arranged side by side and / or stacked. The composition contained in the pouch or its compartments may be a liquid, a solid (such as a powder), or a combination thereof. The composition in the form of a pouch may have a relatively small amount of water, for example, less than about 20% by weight, 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 of water in the detergent composition.

[0133] The treatment composition may be in the form of a spray and may be dispensed, for example, via a trigger sprayer and / or an aerosol container having a valve.

[0134] The treatment composition is 20 seconds -1 and at 21°C, it may have a viscosity of 1 to 1500 centipoise (1 to 1500 mPa * s), 100 to 1000 centipoise (100 to 1000 mPa * s), or 200 to 500 centipoise (200 to 500 mPa * s).

[0135] The treatment composition may contain from about 0.001% to about 30% by weight, preferably from about 0.001% to about 20% by weight, more preferably from about 0.001% to about 15% by weight, 0.001% to about 10% by weight, preferably from about 0.01% to about 5% by weight of a pro-beneficial agent compound of the treatment composition.

[0136] The treatment composition may contain a pro-beneficial agent compound in an amount sufficient to deliver a beneficial agent released by the beneficial agent-promoting compound in an amount of about 0.01 wt% to about 10 wt%, preferably about 0.1 wt% to about 5 wt%, of the treatment composition.

[0137] Auxiliary components The treatment compositions of the present disclosure, which can be consumer products, may contain auxiliary materials. The auxiliary materials may provide benefits in the intended end use of the composition or may be processing aids and / or stabilizing aids.

[0138] Suitable auxiliary materials may include surfactants, conditioning agents, adhesion aids, rheology modifiers or structuring agents, antioxidants, bleaching systems, stabilizers, builders, chelating agents, migration inhibitors, dispersants, enzymes and enzyme stabilizers, catalytic metal complexes, polymeric dispersants, clays and soil release / redeposition inhibitors, optical brighteners, foam suppressants, silicones, hue modifiers, aesthetic dyes, neat fragrances, fragrance delivery systems (core / shell capsules, other perfume materials, etc.), structure elasticizers, carriers, hydrotropes, processing aids, anti-caking agents, coatings, formaldehyde scavengers, and / or pigments.

[0139] 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 auxiliary materials, namely surfactants, conditioning agents, deposition aids, rheology modifiers or structuring agents, antioxidants, bleach activators, surfactants, builders, chelating agents, migration inhibitors, dispersants, enzymes and enzyme stabilizers, catalytic metal complexes, polymeric dispersants, clays and soil release / redeposition inhibitors, optical brighteners, foam suppressants, dyes, additional fragrances and fragrance delivery systems, structure elasticizers, fabric softeners, carriers, hydrotropes, processing aids, structuring agents, anti-caking agents, coatings, formaldehyde scavengers, and / or pigments.

[0140] The exact nature of these additional components and the concentration at which they are incorporated depend on the physical form of the composition and the nature of the operations being performed. 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.

[0141] A. Surfactants The treatment compositions of the present disclosure can include surfactants. Surfactants can be useful, for example, to provide cleaning benefits. The composition may include a surfactant system that can contain one or more surfactants.

[0142] The treatment compositions of the present disclosure may include a surfactant system in an amount of from about 0.1 wt% to about 70 wt%, or from about 2 wt% to about 60 wt%, or from about 5 wt% to about 50 wt% of the composition. Liquid compositions may include a surfactant system in an amount of from about 5 wt% to about 40 wt% of the composition. Compositions suitable for dense formulations, such as dense, liquid, gel, and / or unit dose forms, may include a surfactant system in an amount of from about 25 wt% to about 70 wt%, or from about 30 wt% to about 50 wt% of the composition.

[0143] The surfactant system may include anionic surfactants, nonionic surfactants, zwitterionic surfactants, cationic surfactants, amphoteric surfactants, or combinations thereof. The surfactant system may include linear alkylbenzene sulfonates, alkyl ethoxylated sulfates, alkyl sulfates, nonionic surfactants such as ethoxylated alcohols, amine oxides, or mixtures thereof. The surfactants may be at least partially derived from natural resources such as natural feedstock alcohols.

[0144] Suitable anionic surfactants may include any conventional anionic surfactant. This may include, for example, sulfate detergency surfactants for alkoxylated and / or non-alkoxylated alkyl sulfate materials, and / or sulfonic acid-based detergency surfactants, such as alkylbenzene sulfonate. 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 a mixture thereof. The anionic surfactant may be partially or fully neutralized, for example, by an alkali metal (e.g., sodium) or an amine (e.g., monoethanolamine).

[0145] The surfactant system may contain a nonionic surfactant. Suitable nonionic surfactants include alkoxylated fatty alcohols such as ethoxylated fatty alcohols. Other suitable nonionic surfactants include alkoxylated alkylphenols, alkylphenol condensates, medium-chain branched alcohols, medium-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 surfactant may be linear, branched (e.g., medium-chain branched), or a combination thereof. Certain 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 a C12-C14 EO7 nonionic surfactant.

[0146] Suitable zwitterionic surfactants include betaines such as alkyldimethylbetaine and cocodimethylamidopropylbetaine, C8-C 18 (e.g., C 12 -C 18 ) amine oxides (e.g., C 12 - 14 dimethylamine oxide), and / or N-alkyl-N,N-dimethylamino-1-propanesulfonate (where the alkyl group may be C8-C 18 or C 10 -C 14 ) and any conventional zwitterionic surfactants such as sulfobetaines and hydroxybetaines. The zwitterionic surfactant may include amine oxides.

[0147] Depending on the formulation and / or the intended end use, the composition may substantially not contain a particular surfactant. For example, a liquid fabric softening composition such as a fabric softener may substantially not contain an anionic surfactant because such a surfactant can negatively interact with the cationic component.

[0148] B. Conditioning active substances The treatment composition of the present disclosure may contain a conditioning active substance. A composition containing a conditioning active substance may provide benefits related to softness, wrinkle prevention, antistatic properties, conditioning, anti-stretching, color, and / or appearance.

[0149] The conditioning active substance may be present at a level of about 1% to about 99% by weight of the composition. The composition may contain from about 1% by weight, or from about 2% by weight, or from about 3% by weight, up to about 99% by weight, or up to about 75% by weight, or up to about 50% by weight, or up to about 40% by weight, or up to about 35% by weight, or up to about 30% by weight, or up to about 25% by weight, or up to about 20% by weight, or up to about 15% by weight, or up to about 10% by weight of the conditioning active substance of the composition. The composition may contain from about 5% to about 30% by weight of the conditioning active substance of the composition.

[0150] Suitable conditioning active substances for the compositions of the present disclosure 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 substance is a cationic conditioning active substance, which can improve the delivery / attachment of pro-beneficial agent compounds.

[0151] The treatment composition may contain a conditioning active substance, and the conditioning active substance contains a quaternary ammonium ester compound. Preferably, the quaternary ammonium ester compound is present in the treatment composition at a concentration of about 2% to about 35% by weight, 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, and even more preferably about 7% to about 12% by weight. The quaternary ammonium ester compound (also known as "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 the major part (whether in majority or in plurality) of the ester quaternary ammonium compound. In addition to providing a conditioning effect, it is considered that by selecting an appropriate type and / or concentration of the conditioning active substance (i.e., the quaternary ammonium ester compound), the adhesion and / or performance of the pro-beneficial agent compound described in the present disclosure can be improved.

[0152] The quaternary ammonium ester compound may include compounds according to the following formula, {R 2 (4-m) -N+-[X-Y-R 1 m}A - In the formula, m is 1, 2 or 3, provided that in a given molecule, the value of each m is the same, Each R which may contain 13 to 22 carbon atoms 1 is independently a linear hydrocarbyl group or a branched hydrocarbyl group, preferably, R 1 is linear, more preferably, R 1 is a partially unsaturated linear alkyl chain, Each R 2 is independently a C1-C3 alkyl group or a hydroxyalkyl group, and / or each R 2 ​is 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-, 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-, and 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.

[0153] In the case of monoester quaternary ammonium, m is 1. In the case of diester quaternary ammonium, m is 2. For triester quaternary ammonium, m is 3. The conditioning active substance 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 understood by those skilled in the art, the mixture may depend in part on starting / supply feed materials such as dialkanolamine or trialkanolamine.

[0154] The quaternary ammonium ester compound can 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 can be determined according to the method provided in US Patent Application Publication No. 2020 / 0407665 (corresponding to International Publication No. 2020 / 264566).

[0155] This composition may contain a quaternary ammonium ester compound, a silicone, or a combination of a plurality of these, preferably a combination of one set. The total amount of the quaternary ammonium ester compound and the silicone may be about 5 wt% to about 70 wt% of the composition, or about 6 wt% to about 50 wt%, or about 7 wt% to about 40 wt%, or about 10 wt% to about 30 wt%, or about 15 wt% to about 25 wt%. 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.

[0156] The composition may contain a mixture of different types of conditioning active substances. The composition of the present disclosure may contain a specific conditioning active substance, but may not substantially contain other conditioning active substances. For example, the composition may not contain a quaternary ammonium ester compound, a silicone, or both. The composition may contain a quaternary ammonium ester compound, but may not substantially contain a silicone. The composition may contain a silicone, but may not substantially contain a quaternary ammonium ester compound.

[0157] The conditioning active substance may include a glyceride copolymer. The glyceride copolymer may be derived from natural oils. Examples of natural oils include, but are not limited to, vegetable oils, algal oils, fish oils, animal fats, tall oil, derivatives of these oils, combinations of any of these oils, etc. 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, camellia oil, hempseed 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 production. The glyceride copolymer may be a metallized unsaturated polyol ester.

[0158] C. Adhesion Aid The treatment composition of the present disclosure may include an adhesion aid. The adhesion aid can promote the adhesion of various beneficial agents including the pro-beneficial agent compounds, conditioning active substances, fragrances or fragrance delivery systems (such as encapsulated fragrances), or combinations thereof of the present disclosure, improve the performance effects of the composition, and / or enable more efficient formulations of such beneficial agents. The composition may include from 0.0001 wt% to 3 wt%, preferably from 0.0005 wt% to 2 wt%, more preferably from 0.001 wt% to 1 wt%, or about 0.01 wt% to about 0.5 wt%, or about 0.05 wt% to about 0.3 wt% of the adhesion aid. The adhesion aid may be a cationic or amphoteric polymer, preferably a cationic polymer.

[0159] General cationic polymers and methods for their production are well-known in the literature. Suitable cationic polymers include quaternary ammonium polymers known as "polyquaternium" polymers named by the International Nomenclature of Cosmetic Ingredients, for example, polyquaternium-6 (poly(diallyldimethylammonium chloride)), polyquaternium-7 (copolymer of acrylamide and diallyldimethylammonium chloride), polyquaternium-10 (quaternized hydroxyethyl cellulose), polyquaternium-22 (copolymer of acrylic acid and diallyldimethylammonium chloride), and the like.

[0160] The adhesion aid may be selected from the group consisting of polyvinylformamide, partially hydroxylated polyvinylformamide, polyvinylamine, polyethyleneimine, ethoxylated polyethyleneimine, polyvinyl alcohol, polyacrylate, and combinations thereof.

[0161] The cationic polymer may contain cationic acrylate and / or cationic methacrylate. Such a polymer may be a copolymer further containing a nonionic monomer such as acrylamide, for example. The cationic polymer may be linear or crosslinked. The adhesion aid may contain a combination of a linear cationic polymer and a crosslinked cationic polymer.

[0162] The adhesion aid can be added to the consumer product composition simultaneously with the delivery particles (e.g., simultaneously with an encapsulated beneficial agent such as an encapsulated perfume) or directly / independently. The weight average molecular weight of the polymer, when measured by size exclusion chromatography against a polyethylene oxide standard using refractive index (RI) detection, 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. The weight average molecular weight of the cationic polymer may be 5,000 daltons to 37,500 daltons.

[0163] D. Perfumes and / or perfume delivery systems The treated compositions of the present disclosure may include perfumes and / or perfume delivery systems. This may apply even when the beneficial agent fragment of the pro-beneficial agent compound is derived from a perfume raw material.

[0164] The treated compositions of the present disclosure may include other perfume raw materials, for example, in undiluted or free form, including PRMs that do not contain aldehyde or ketone moieties. For example, other PRMs may be provided as undiluted oil or free oil in the premix composition and / or treated composition according to the present disclosure even if they do not react with the pro-beneficial agent precursor compound. Such mixtures may be desirable, for example, to provide a more appropriate olfactory experience.

[0165] The treated compositions of the present disclosure may further include undiluted perfumes, preferably undiluted perfume raw materials that do not contain aldehyde or ketone moieties. Preferably, the undiluted perfume includes alcohol-containing perfume raw materials. 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 include free perfume raw materials that contain aldehyde and / or ketone moieties.

[0166] The treated compositions of the present disclosure may additionally or alternatively include a perfume delivery system. Such a perfume delivery system may take the form of a polymer-assisted delivery system. Such a perfume delivery system may take the form of a capsule, for example, a core-shell capsule, where the core contains a perfume raw material and is surrounded by a polymer shell. The polymer shell may include a polymer material derived from polyacrylate, polyurea, polyurethane, polysaccharide, polyvinyl alcohol, melamine, derivatives thereof, or combinations thereof. Additionally or alternatively, a suitable perfume delivery system may include known pro-perfume / pro-fragrance materials.

[0167] Other materials The treatment compositions, and / or further premix compositions, of the present disclosure may include unreacted reactants and / or decomposition products of the pro-beneficial agent compounds described herein. For example, the treatment compositions and / or premix compositions of the present disclosure may include precursors or derivatives of carbon-containing cores alone, such as parent amino acids (e.g., H2-A-H, wherein A is as defined substantially above according to Formula III, and wherein G = oxygen), hydrophobic modified amino acids (e.g., H2-A-Q, wherein A is as defined substantially above according to Formula III), free forms of hydrophobic substances (e.g., H-G-Q such as fatty alcohols like dodecanol), forms of pro-beneficial agent compounds without hydrophobic substances (e.g., Z-A-H, wherein A is as defined substantially above according to Formula III and G = oxygen), free beneficial agents, such as aldehyde- or ketone-containing PRM, or combinations thereof.

[0168] Method for manufacturing a treatment composition The present disclosure relates to a manufacturing process for any of the compositions described herein. The manufacturing process of a treatment composition, which can be a consumer product, may include the step of combining a pro-beneficial agent compound described herein with an auxiliary material described herein.

[0169] The pro-beneficial agent compound can be combined with such auxiliary materials by methods including mixing and / or spraying.

[0170] The compositions of the present disclosure can be formulated into any suitable form and can be prepared by any process selected by the formulator. The pro-beneficial agent compound and the auxiliary material may be combined in a batch process, a circulation loop process, and / or an in-line mixing process. Suitable apparatuses for use in the processes disclosed herein include continuous stirred tank reactors, homogenizers, turbine stirrers, recirculation pumps, paddle mixers, high-shear mixers, static mixers, plow shear mixers, ribbon blenders, vertical axis granulators, and drum mixers (all batch-type and, where available, of continuous process configuration), spray dryers, and extrusion machines.

[0171] For example, the method for manufacturing a treatment composition may include combining a pro-beneficial agent compound according to the present disclosure with a base composition, preferably a liquid base composition, and the base composition includes auxiliary components. This process can be carried out, for example, in a batch process or an in-line mixing process, preferably an in-line mixing process.

[0172] The method for manufacturing a treatment composition may include combining a pro-beneficial agent precursor compound, a beneficial agent, and an auxiliary component as described herein. Preferably, the auxiliary component is part of the base composition, and the pro-beneficial agent precursor compound and the beneficial agent are each added to the base composition as separate inputs. The separate inputs may be added sequentially (e.g., continuously) or substantially simultaneously. Preferably, the base composition is liquid. This process can be carried out, for example, in a batch process or an in-line mixing process, preferably an in-line mixing process.

[0173] The method for manufacturing a treatment composition may include adding a premix to the base composition. The premix composition may include a pro-beneficial agent precursor compound and a beneficial agent as described herein. The premix composition can be obtained by combining a pro-beneficial agent precursor compound and a beneficial agent as described herein. The premix composition may include, for example, a pro-beneficial agent compound according to the present disclosure due to the reaction of the precursor compound and the beneficial agent. The premix composition may include a mixture of a pro-beneficial agent precursor compound, a beneficial agent, and a pro-beneficial agent compound. The premix may optionally contain water. This process can 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 in solid form, such as a PEG-based pastille, or may be particularly preferred when producing a treatment composition in solid form. 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 distillation in vacuo.

[0174] Method for treating a surface The present disclosure further relates to a method for treating a surface (e.g., the surface of an article) with a treatment composition according to the present disclosure. Such methods can provide benefits related to cleaning, conditioning, hygiene, and / or a cooling effect.

[0175] Suitable surfaces can include fabrics (including clothing, towels, or linens), hard surfaces (such as tiles, porcelain, linoleum, or wooden floors), tableware, hair, skin, or mixtures thereof.

[0176] The method may include contacting the article or surface with the treatment composition of the present disclosure, optionally in the presence of water, and may further optionally 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 solution. The treatment composition may be diluted with water before, during, or after contact with the surface or article. The surface or article may optionally be washed and / or rinsed before and / or after the contacting step.

[0177] A method for treating and / or cleaning a surface may include the following steps. a) Optionally, washing, rinsing, and / or drying the surface; b) Optionally, contacting the surface with the treatment composition described herein, in the presence of water; c) Optionally, washing and / or rinsing the surface; and d) Optionally, drying by passive drying and / or by an active method such as a washing machine dryer.

[0178] For the purposes of the present invention, washing includes, but is not limited to, scrubbing and mechanical agitation. The fabric may include any fabric that can be washed or treated under normal consumer or industrial use conditions.

[0179] Liquids that may contain the disclosed compositions can have a pH of from about 3 to about 11.5. When diluted, such compositions are typically used at a concentration of from 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 part of a fabric, the weight ratio of water to fabric is typically from about 1:1 to about 30:1.

[0180] The present disclosure further discloses a process for treating a surface or an article, preferably a fabric, with an aqueous treatment liquid comprising a pro-beneficial agent precursor compound according to the present disclosure, preferably wherein the beneficial agent fragment is a fragment of a fragrance raw material or an antibacterial agent, preferably a fragment of a fragrance raw material. The process may include contacting the surface or article, preferably the fabric, with the aqueous liquid. The pro-beneficial agent compound may be present in the aqueous liquid at a concentration of from about 0.001 weight ppm (e.g., 1 ppb) to about 1000 weight ppm.

[0181] The present disclosure further discloses a process for treating a surface or an article, preferably a fabric, with an aqueous treatment liquid comprising a pro-beneficial agent precursor compound according to the present disclosure and a beneficial agent according to the present disclosure. The beneficial agent may be a fragrance raw material or an antibacterial agent, preferably a fragrance raw material. The method may include contacting the surface or article, preferably the fabric, with the aqueous liquid. The pro-beneficial agent precursor compound may be present in the aqueous liquid at a concentration of from about 001 ppm (e.g., 1 ppb) to about 1000 weight ppm.

[0182] Use The present disclosure relates to the use of the pro-beneficial agent compounds described herein for providing a freshness effect, particularly when the pro-beneficial agent compound contains a fragment of a fragrance raw material and is part of a treatment composition.

[0183] The present disclosure relates to the use of the pro-beneficial agent compounds described herein for providing an antibacterial effect, particularly when the pro-beneficial agent compound contains a fragment of an antibacterial agent and is part of a treatment composition.

[0184] The present disclosure relates to the use of the pro-beneficial agent compounds described herein for providing an anti-odor effect, particularly when part of a treatment composition.

[0185] Combination The specifically contemplated combinations of the present disclosure are described herein in the following alphabetically labeled paragraphs. These combinations are essentially for illustrative purposes and are not intended to be limiting.

[0186] A. A carbon-containing core comprising a carbon skeleton, one or more side groups, a nitrogen atom, and a carbonyl group, wherein the carbonyl group is part of a carbonyl-containing moiety selected from an ester moiety, an amide moiety, or a thioester moiety, the carbonyl-containing moiety contains a heteroatom bonded to the carbon of the carbonyl group, the heteroatom is selected from oxygen, nitrogen, or sulfur, the carbonyl-containing moiety further contains a hydrophobic moiety bonded to the heteroatom, the hydrophobic moiety is an organic group containing 5 to 34 chain atoms, preferably carbon chain atoms, a carbon-containing core, and a beneficial agent fragment bonded to the core by a linking bond that is a single bond or a double bond, the linking bond is between the nitrogen atom of the carbon-containing core and the carbon atom of the beneficial agent fragment, the single bond, if present, is formed by a 1,4-addition process, the double bond, if present, is part of an imine bond, and when the linking bond cleaves, the beneficial agent is released, the beneficial agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof, a beneficial agent fragment, and a pro-beneficial agent compound.

[0187] B. The pro-beneficial agent compound according to paragraph A, wherein the carbon skeleton contains 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms, more preferably 1 carbon atom.

[0188] C. The pro-beneficial agent compound according to either paragraph A or B, wherein the carbon-containing core is selected from the group consisting of amino acids, preferably proteinogenic amino acids, even more preferably proteinogenic amino acids selected from valine, phenylalanine, leucine, isoleucine, or combinations thereof, more preferably valine, phenylalanine, or combinations thereof.

[0189] D. At least one side group is a side group of a protein - constituting amino acid or a derivative thereof, preferably a side group of a protein - constituting amino acid selected from the group consisting of valine, phenylalanine, leucine, isoleucine, derivatives thereof, or combinations thereof, more preferably having the structure of valine, phenylalanine, derivatives thereof, or combinations thereof, the pro - beneficial agent precursor compound according to any one of paragraphs A - C.

[0190] E. The pro - beneficial agent compound according to any one of paragraphs A - D, wherein the carbonyl - containing moiety is an ester moiety.

[0191] F. The pro - beneficial agent compound according to any one of paragraphs A - E, wherein the hydrophobic moiety is an organic group containing about 8 to about 18 chain atoms, preferably about 8 to about 14 chain atoms, more preferably carbon chain atoms.

[0192] G. The pro - beneficial agent compound according to any one of paragraphs A - F, wherein the hydrophobic moiety is an unsubstituted organic group, an unbranched organic group, or a combination thereof, preferably a combination thereof.

[0193] H. The pro - beneficial agent compound according to any one of paragraphs A - G, wherein the hydrophobic moiety contains a second fragment of a second beneficial agent, preferably the second beneficial agent is a fragrance raw material, more preferably the second beneficial agent is an alcohol - containing fragrance raw material.

[0194] I. The pro - beneficial agent compound according to any one of paragraphs A - H, wherein the beneficial agent fragment is derived from a beneficial agent containing an aldehyde moiety.

[0195] J. The pro - beneficial agent compound according to any one of paragraphs A - I, wherein the beneficial agent fragment is derived from a beneficial agent containing a ketone moiety.

[0196] The pro-beneficial agent compound according to any one of paragraphs A to J, wherein the beneficial agent fragment is derived from a beneficial agent selected from a fragrance raw material, an antibacterial agent, an insecticide, an insect repellent, an antifungal agent, a herbicide, a hue dye, an antioxidant, a non-fragrance sensory stimulant, or a combination thereof, preferably a fragrance raw material, an antibacterial agent, or a combination thereof, more preferably a fragrance raw material.

[0197] L. The beneficial agent is a fragrance raw material, preferably methyl nonyl acetaldehyde, benzaldehyde, floralozone, isocyclocitral, triplal (ligustral), presilkeemon B, lilial, decyl aldehyde, undecylenic aldehyde, cyclamen homologue aldehyde, cyclamen aldehyde, Dupical, oncidar, adoxal, melonal, calypsone, anisaldehyde, heliotropin, cumin aldehyde, scentenal, 3,6-dimethylcyclohex-3-ene-1-carbaldehyde, satenal, 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, butyl cinnamaldehyde, limoneral, amyl cinnamaldehyde, hexyl cinnamaldehyde, citronellal, citral, cis-3-hexen-1-al, neryl oxide, 4-(4-methoxyphenyl)butan-2-one, 1-naphthalen-2-ylethanone, nectaryl, trimofix O, fluramon, delta-damascone, beta-damascone, alpha-damascone, methyl ionone, 2-hexylcyclopent-2-en-1-one, galvascon, and a mixture thereof, and more preferably, the hydrophobic moiety is an organic group containing about 8 to about 18 chain atoms, preferably the chain atoms are carbon atoms, the pro-beneficial agent compound according to any one of paragraphs A to K.

[0198] M. The pro-beneficial agent is an antibacterial agent, preferably an antibacterial agent selected from acetylacetone enolate, gossypol, nutkatone, or a mixture thereof, more preferably an organic group in which the hydrophobic moiety contains about 6 to about 12 chain atoms, preferably the chain atoms are carbon atoms, the pro-beneficial agent compound according to any of paragraphs A to L.

[0199] N. The pro-beneficial agent compound is characterized by the structure according to formula I, Z ** A-Q Formula I wherein A represents a carbon-containing core, Z is a beneficial agent fragment, ** represents a linking bond between the nitrogen atom of the A group and the carbon atom of the Z group, and the linking bond is (a) a double bond, thereby forming an imine bond, or (b) when the beneficial agent from which the beneficial agent fragment is derived contains an alpha-beta unsaturated carbonyl-containing moiety that is an aldehyde moiety or a ketone moiety, one of the single bonds formed from a 1,4-addition, wherein Q is a hydrophobic moiety and is a monovalent organic group, the pro-beneficial agent compound according to any of paragraphs A to M.

[0200] O. The compound is characterized by the structure according to formula II,

[0201]

Chemical formula

[0202] P.G = -O-, m ≧ 1, R 1 has the structure of the side group of a proteinogenic amino acid, R 2 is H, Z is a fragment of a fragrance raw material, Q is an organic group containing about 8 to about 18 chain atoms, preferably the chain atoms are carbon atoms, the pro-beneficial agent compound described in paragraph O.

[0203] Q. A treatment composition comprising an auxiliary component and the pro-beneficial agent compound described in any of paragraphs A - P.

[0204] R. The auxiliary component is selected from the group consisting of surfactants, conditioning active substances, adhesion aids, rheology modifiers or structuring agents, antacids, bleaching systems, stabilizers, builders, chelating agents, migration inhibitors, dispersants, enzymes, enzyme stabilizers, catalytic metal complexes, polymer dispersants, soil and stain removal / redeposition inhibitors, optical brighteners, foam suppressants, silicones, hue modifiers, aesthetic dyes, neat fragrances, fragrance delivery systems, structure elasticizers, carriers, hydrotropes, processing aids, anti-agglomerants, coatings, formaldehyde scavengers, and / or pigments, the treatment composition described in paragraph Q.

[0205] The conditioning aid component contains a conditioning active, preferably the conditioning active contains a quaternary ammonium ester compound, more preferably the quaternary ammonium ester compound is present at a concentration of about 2 wt% to about 35 wt%, preferably about 4 wt% to about 25 wt%, more preferably about 5 wt% to about 20 wt%, preferably about 6 wt% to about 15 wt%, more preferably about 7 wt% to about 12 wt% of the treatment composition, the treatment composition according to either paragraph Q or R.

[0206] T. The treatment composition further comprises an undiluted fragrance, preferably an undiluted fragrance comprising a fragrance raw material containing alcohol, the treatment composition according to any one of paragraphs Q to S.

[0207] U. 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 a combination thereof, the treatment composition according to any one of paragraphs Q to T.

[0208] V. 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 soluble sheet, a pastille or bead, a fibrous article, a tablet, a stick, a bar, a flake, a foam / mousse, a non-woven sheet, or a mixture thereof, the treatment composition according to any one of paragraphs Q to U.

[0209] W. The pro-benefit agent compound is present in the detergent composition at a concentration of about 0.001 wt% to about 30 wt% of the treatment composition, the treatment composition according to any one of paragraphs Q to V.

[0210] X. A premix composition comprising a pro-beneficial agent precursor compound, the precursor compound comprising a carbon-containing core, the carbon-containing core comprising a carbon skeleton, one or more side groups, a nitrogen atom, and a carbonyl group, the carbonyl group being part of a carbonyl-containing moiety selected from an ester moiety, an amide moiety, or a thioester moiety, the carbonyl-containing moiety comprising a heteroatom bonded to the carbon of the carbonyl group, the heteroatom being selected from oxygen, nitrogen, or sulfur, the carbonyl-containing moiety further comprising a hydrophobic moiety bonded to the heteroatom, the hydrophobic moiety being an organic group comprising 5 to 34 chain atoms; a beneficial agent, the beneficial agent comprising an aldehyde moiety, a ketone moiety, or a combination thereof, the pro-beneficial agent precursor and the beneficial agent being capable of optionally reacting according to any of paragraphs A - P to form a pro-beneficial agent compound, and the sum of the weight percentages of the pro-beneficial agent precursor, the beneficial agent, and the pro-beneficial agent compound, when present, being from about 10 wt% to about 100 wt%, preferably from about 25 wt% to about 100 wt%, more preferably from about 50 wt% to about 100 wt%, even more preferably from about 75 wt% to about 100 wt% of the premix composition when present; and a beneficial agent.

[0211] Y1. The premix composition according to paragraph X, wherein the premix composition further comprises water, preferably the premix composition is in the form of an emulsion, more preferably an oil-in-water emulsion.

[0212] Y2. The premix composition according to paragraph X, wherein the premix composition comprises less than about 10 wt%, preferably less than 5 wt%, more preferably less than 1 wt%, even more preferably less than 0.1 wt% water of the premix composition.

[0213] Z. The premix composition according to any of paragraphs X, Y1, or Y2, wherein the molar ratio of the pro-beneficial agent precursor compound to the beneficial agent is from about 3:1 to about 1:3, preferably from about 2:1 to about 1:2, more preferably from about 1.5:1 to about 1:1.5, even more preferably from about 1.2:1 to about 1:1.2, and even more preferably about 1:1.

[0214] A method for preparing a treatment composition according to any one of claims Q to W, comprising at least one of the following: (a) a step of combining a pro-beneficial agent compound with an auxiliary component, preferably, the auxiliary component is part of the base composition; (b) a step of combining a premix composition according to any one of claims X to Z with an auxiliary component, preferably, the auxiliary component is part of the base composition; (c) a step of combining a pro-beneficial agent precursor compound, a beneficial agent, and an auxiliary component, preferably, the auxiliary component is part of the base composition, and the pro-beneficial agent precursor compound and the beneficial agent are added to the base composition as separate inputs, the method.

[0215] BB. A method for treating an article or a surface, comprising treating the article or the surface with the treatment composition according to any one of paragraphs Q to W, optionally in the presence of water, and further optionally comprising the steps of rinsing and / or drying the article or the surface.

[0216] Test method Preparation of a premix fluid (e.g., waterless) The premix fluid can be prepared as follows.

[0217] Method A: A beneficial agent containing an aldehyde or ketone moiety is added in a molar equivalent approximately equal to the molar concentration of the amine radical present in the precursor compound (e.g., the precursor compound of formula I above). This material is stirred at 150 rpm for at least 12 hours using a magnetic stir bar.

[0218] Method B: A beneficial agent containing an aldehyde or ketone moiety is added in a molar equivalent approximately equal to the molar concentration of the amine radical present in the precursor compound (e.g., the precursor compound of formula V above). This material is stirred at 150 rpm for at least 12 hours using a magnetic stir bar in the presence of a water scavenger. The resulting fluid can be mechanically filtered or added directly to the treatment composition.

[0219] As an illustrative example, the IKA RW20DSl mixer, model RW20DSl, and the IKA R 1 342 impeller blade are used at 350 rpm to combine 59 parts by weight of a modified amino acid as disclosed in Synthesis Example 3A below with 41 parts by weight of a beneficial agent (e.g., cyclamen aldehyde).

[0220] Preparation of a premix emulsion (e.g., with water) The premix emulsion can be prepared as follows.

[0221] Method A: Starting from 1 part by weight of the premix fluid provided in the previous example, add diethylene glycol monobutyl ether (10.0 parts, e.g., TCI) and ECOSURF™ EH-9 (1 part, e.g., The Dow Chemical Company). Add the mixture to a Flacktek DA150.FVZ-K speed mixer at 3,500 rpm for 1 minute. Add water (88 parts in total) in two equal portions. After each addition of water, mix the mixture at 3,500 rpm for 10 - 15 minutes using a Flacktek DA150.FVZ-K speed mixer.

[0222] Method B: Starting from 1 part by weight of a precursor compound (e.g., a hydrophobic modified amino acid), add diethylene glycol monobutyl ether (10.0 parts, e.g., TCI) and ECOSURF™ EH-9 (1 part, e.g., The Dow Chemical Company). Add the mixture to a Flacktek DA150.FVZ-K speed mixer at 3,500 rpm for 1 minute. Add water (88 parts in total) in two equal portions. After each addition of water, mix the mixture at 3,500 rpm for 10 - 15 minutes using a Flacktek DA150.FVZ-K speed mixer. The beneficial agent is added in a molar equivalent approximately equal to the molar concentration of the amine radical present in the precursor compound.

[0223] As an illustrative example, 99 parts by weight of an emulsified fluid emulsified as described above and containing a modified amino acid as disclosed in the following Synthetic Example 1 (including about 1 part by weight of the modified amino acid) is combined with 1 part of a beneficial agent (e.g., cyclamen aldehyde).

[0224] Preparation of Test Fabric Softener / Enhancer Composition Provide 7.5% by weight of N,N - bis(tallow oil oxyethyl)-N,N - dimethylammonium chloride in an aqueous mixture. The above - mentioned premix fluid, the above - mentioned premix emulsion, or two separate undiluted fluids (one a pro - beneficial agent precursor such as a modified amino acid and the other a beneficial agent such as one or more fragrance raw materials) are added in amounts such that the concentration of the beneficial agent or beneficial substance fragment in the fabric softener is about 0.3% by weight of the final fabric softener composition. The mixture is stirred at 350 rpm for 5 minutes using an IKA RW 20 D Sl mixer, model RW20DSl, and an IKA R1342 impeller blade. A structuring agent and an adhesion aid are added and the mixture is stirred for 10 minutes. Water is added as necessary to standardize the concentration of N,N - bis(tallow oil oxyethyl)-N,N - dimethylammonium chloride between the test runs to 7.3% by weight, and the mixture is stirred for 5 minutes. The pH is adjusted to 2 - 3 with HCl if necessary.

[0225] Preparation of Test Pastille Composition Provide a mixture of 92.59 parts by weight of a molten PEG - 8000 material and 6.00 parts by weight of a fragrance accord. Add 0.59 part by weight of the pro - beneficial agent premix fluid of Synthetic Example 1 to a high - speed mixer cup. Quickly place the speed mixer cup into a Flacktek DA150.FVZ - K speed mixer at 3500 rpm for 1 minute. 4 o Pour into a blue silicone - treated rubber mold pre - equilibrated at 4 °C and spread with a 10” plastic taping knife to immediately make sample pastilles from the mixture. Cool the incense tablets at room temperature for about 30 minutes, then remove the pastilles from the mold and store under ambient conditions.

[0226] Preparation of Test Fabric Detergent Composition To 97.58 parts by weight of TIDE Original Scent liquid detergent, 2.42 parts by weight of the pro-beneficial agent-compound premix fluid of Synthesis Example 3B is added. The amount is selected such that the concentration of the selected beneficial agent or beneficial substance fragment in the final detergent is about 1% by weight after the fabric treatment composition. Using an IKA RW 20 D Sl mixer, model RW20DSl, and an IKA R1342 impeller blade, the mixture is stirred at 350 rpm for 10 minutes.

[0227] Preparation of Liquid Detergent for Dishwashing 0.6 part by weight of the pro-beneficial agent compound premix fluid is added to 99.4 parts by weight of Ultra Dawn Blue Diswashing Liquid. The pro-beneficial agent amino acid ester is added in an amount such that the concentration of the beneficial agent or beneficial substance fragment in the dishwashing liquid is about 0.2% by weight after composition. The mixture is mixed on a Thermo Scientific Tube Roller, Model No. 88881003 at 80 rpm for 1 hour.

[0228] A. Method for Preparing Fabric To prepare fabric for headspace analysis testing, a fabric sample (100% cotton terry cloth, item number ITL 1022-15PGP, Calderon Textiles, Inc. 6131 W.80 th St., Indianapolis, IN 46278, scoured and conditioned in three washing cycles of detergent and fabric softener) is treated with detergent or fabric softener in a manner consistent with North American consumers via a mini-clothes washer, full-scale washer, and clothes dryer. Prior to headspace GCMS analysis (see the following method), unless otherwise noted, the fabric is equilibrated at 21.1 °C and 50% relative humidity for 12 - 24 hours. The ballast load consists of samples of cotton and polycotton knit in a size of 20 x 20 inches (50 x 50 cm).

[0229] Washing Treatment Conditions In the following fabric strengthener / softener composition performance test, the fabric is treated under the following washing conditions. Washing: Stir for 12 minutes at 30.6 °C. Rinsing: Stir for 2 minutes at 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. In the following pastille composition performance test, the fabric is treated under the following washing conditions. A North America Kenmore 600 series top-loading washing machine is used. Each machine is set to run a normal single cycle including a 12-minute washing agitation period and one 3-minute rinse. The water used had a hardness of 137 ppm, was at 30.6 °C for each wash, and 15.5 °C for the rinse. The volume of water in each process was 64 liters. The total fabric load weight was 3.6 kg (including 32 test fabric hand towels, 9 100% cotton ballast, and approximately 5 50 / 50 poly-cotton ballast). The detergent used was fragrance-free liquid TIDE Original Scent (manufactured by The Procter & Gamble Company). While the wash water is being filled, 81 g of the detergent is added to the wash water. Also, after adding the detergent, 25 g of the pastille to be evaluated is added, followed by the fabric load. After the water filling is complete, the machine enters the agitation period. Subsequently, a wash agitation (normal setting) and a rinse process (with the corresponding spin cycle) are carried out. After the wash process is complete, the fabric is removed. The test fabric is machine dried for 50 minutes in a Kenmore dryer set to Cotton / High or the test fabric is line dried for 16 hours in a room controlled at 21.1 o °C / 50% relative humidity.

[0230] In the following detergent composition performance test, the fabric is treated under the following washing conditions. Washing: Stir for 12 minutes at 30.6 °C. Rinsing: Stir for 2 minutes at 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.

[0231] Headspace Analysis on Fabric Use the following procedure to determine the level of fragrance ingredients in the headspace on the fabric.

[0232] The following equipment is used: Gas chromatograph 7890B equipped with a mass selective detector (5977B) (MSD) and ChemStation quantification package, Gerstel multi-purpose sampler equipped with a solid phase microextraction (SPME) probe or a similar system, divinylbenzene / Carboxen / polydimethylsiloxane SPME fiber from Supleco part #57298-U (or a similar fiber), nominal diameter 30mx0.25mm, film thickness 0.25μm, J&W 122-5532UI DB-5, 20mL headspace vial.

[0233] To prepare the fabric for analysis, cut three 2.54cm x 5.08cm cotton swatches from the cotton terry prepared and processed by the above method. Place each piece into a 20mL headspace vial and cap.

[0234] The parameters of the Gerstel autosampler are as follows: from SPME-incubator, incubation temperature - 65°C, incubation time - 10.00 minutes sample parameters, vial penetration - 22.00mm, extraction time - 5.00 minutes, initial penetration - 54.00mm, desorption time - 300 seconds. The GC oven parameters for the front SS inlet He are as follows: mode - splitless, heater: 270°C, GC operation time - 14.28 minutes. For the oven, initial temperature - 40°C, hold time - 0.5 minutes, heating program - at a rate of 17°C / min, temperature of 270°C, hold time of 0.25 minutes. The MSD parameters are as follows. In scan mode, run with a minimum range of 35 - 350 m / z.

[0235] Generate a calibration curve from standard beneficial materials. Use the ChemStation software (or similar quantification software) and the calibration curve of each fragrance component to calculate the mass in the headspace.

[0236] Color change of the composition The treatment composition may be tested for color change according to the following procedure. L * , a * , and b * The reflectance spectrum and color measurement including are made using a LabScan XE reflectance spectrophotometer (Hunter Labs, Reston, VA, D65 light source, 10-degree field of view, excluding ultraviolet light). L for the treatment composition * , a * and b * values are measured at time t 初期 , i.e., at the start of the test after mixing in the beneficial agent, and t 最終 , i.e., at the end of the stability test defined in each experiment. The total color change (ΔE) of the treatment composition is calculated based on the data collected at each time point t using the following formula: ΔE t = ((L * c - L * s ) 2 + (a * c - a * s ) 2 + (b * c - b * s ) 2 ) 1 / 2 (where the subscripts c and s refer to the control, i.e., the treatment composition without the beneficial agent, and the sample, i.e., the treatment composition with each aldehyde / ketone beneficial agent, respectively, and here, the values used to calculate ΔE t are the values at the corresponding time points t (t 初期 , t 最終 ).

[0237] Samples were prepared by adding a professional beneficial agent fluid premix (without water) to the base treatment composition while overhead mixing using an IKA RW 20 impeller for the blade and gently mixing for 15 minutes. The treatment composition was placed in a 50 mL (25 cm 2)Put it into a CELLSTAR (registered trademark) cell culture flask. t at a specific temperature 初期 and t 最終 Subsequently, measure the color appearance of each treatment composition sample with a LabScan XE 10 reflectance spectrophotometer (Hunter Labs, Reston, VA, B.D65 light source, 10-degree field of view, excluding ultraviolet light).

[0238] HLB value of nonionic surfactant Nonionic surfactants can be classified by the balance between the hydrophilic and lipophilic parts in the surfactant molecule. The hydrophilic-lipophilic balance (HLB) scale devised by Griffin in 1949 is a scale of 0 - 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 part of the molecule and M is the molecular weight of the whole molecule, and the result is given on a scale of 0 - 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, W.C. Calculation of HLB values of Nonionic Surfactants, J. Soc. Cosmet. Chem. 1954, 5, 249 - 256. The 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 the weighted average of the HLB values of the surfactants.

[0239] Test method for determining logP The value of the logarithm of the octanol / water partition coefficient (logP) is calculated for materials as described herein (such as hydrophobic substances / Q groups or alcohol versions of PRMs).

[0240] The logP value of each PRM was calculated using the Consensus logP Computational Model, version 14.5 (Linux®), available from Advanced Chemistry Development Inc. (ACD / Lab) (Toronto, Canada), and a unitless logP value was obtained. The ACD / Labs Consensus logP Computational Model is part of the ACD / Labs model suite.

Example

[0241] The examples provided below are intended to be illustrative in nature and not limiting.

[0242] Synthesis Examples The following Synthesis Examples 1 to 17 illustrate the synthesis of exemplary pro-beneficial agent compounds (e.g., Synthesis Example 1) and their amine-containing precursors (e.g., Synthesis Example 1’) according to the present disclosure.

[0243] Comparative Synthesis Example A shows a comparative amino-modified silicone polymer that does not contain the small molecule amino acid ester moiety provided in the present disclosure. Comparative Synthesis Examples B and C are modified amino acid esters derived from materials outside the scope of the present invention.

[0244] For consistency and illustrative / comparative purposes, each example reacts different undiluted fragrance precursors with the same fragrance raw material, cyclamen aldehyde (containing an aldehyde moiety) having the following structure. As an additional example (formed via 1,4-addition), Synthesis Example 3B forms a pro-beneficial agent compound having delta-damascone containing a ketone moiety. The structure of the PRM is shown below.

[0245]

Chemical formula

[0246] However, it is understood that other aldehyde or ketone-containing beneficial agents according to the present disclosure may also result in the formation of suitable pro-beneficial agent compounds. Some of these are illustrated and tested in the performance examples below.

[0247] It is also understood that the synthetic examples may be formulated into the treatment composition as a liquid premix emulsion, or as an undiluted 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 directly formulated as a liquid premix fluid in the treatment composition unless otherwise indicated.

[0248] For each synthetic example, the resulting pro-beneficial agent compound is presented with cyclamen aldehyde (or in the case of Synthetic Example 3B, delta-damascon) and provided in Table D below. Comparative Synthetic Example A, a silicone-based pro-fragrance, is exemplified by cyclamen aldehyde in Table D but does not contain a hydrophobic pro-beneficial amino acid ester and is not considered to be of low molecular weight by those skilled in the art.

[0249] Comparative Synthetic Example A. Cyclamen aldehyde (0.35 g, available from Symrise, Holzminden, Germany) is added to amino-modified silicone (A’), KF-8003 (5 g, available from Shin-Etsu Silicones of America Inc., Akron, OH). The mixture is stirred for 12 hours. The resulting clear fluid (Synthetic Example A) is 1 analyzed by 1H NMR.

[0250] As shown in Table D below, the resulting material of Comparative Synthetic Example A does not contain a hydrophobic ester moiety according to the present disclosure.

[0251] The materials used in both the performance and stability examples were based on the emulsion silicone systems exemplified herein. Starting from 60.0 parts by weight of the KF-8003 compound, Surfonic L24-9 (2.0 parts, e.g., Huntsman Holland BV) and Tergitol™ 15-S-40 (2.5 parts, e.g., The Dow Chemical Company) are added. The mixture is mixed for 1 minute at 800 rpm using an IKA RW 20. Water (35.5 parts in total) is added in two equal portions. After each addition of water, the mixture is mixed with the IKA RW 20 for approximately 10 - 15 minutes.

[0252] Next, the beneficial agent is added to the emulsion in a molar equivalent approximately equal to the molar amount of amine in the KF-8003 silicone polymer and stirred for 15 minutes at 275 rpm using an IKA RW 20. As an exemplary example, 93.5 parts by weight of the silicone fluid emulsified as described above and disclosed above is combined with 6.5 parts by weight of a fragrance raw material (e.g., cyclamen aldehyde).

[0253] Comparative Synthesis Examples B and C. Methyl or ethyl esters of amino acids (available from Sigma-Aldrich) are provided and neutralized. Next, the comparative pro-beneficial agent compound is prepared according to the general method B shown below.

[0254] Method for preparing a pro-beneficial agent compound (e.g., modified amino acid ester) In the following synthesis examples, materials are generally obtained / available from Sigma-Aldrich (St. Louis, MO, USA), except as indicated below. Amino acids are generally provided with a purity of >98% or even >99%. Alcohols are generally provided with a purity of >97%, >98%, or even >99%. Cyclamen aldehyde (e.g., Sigma-Aldrich) is provided >95% pure. δ-Damascone is available from Firmenich (Geneva, Switzerland). C10PO1 was prepared from the propoxylation of decanol. ISALCHEM 123 and NEODOL 123 were obtained from Sasol (Viale Forlanini, Milano, Italy).

[0255] General Method A: General Preparation of Precursor Compounds (e.g., Amino Acid Esters) To prepare a pro-beneficial agent precursor compound from an amino acid and an alkyl alcohol, a round-bottom flask is charged with 1 equivalent of the free base amino acid starting material. To the flask, 1 equivalent of the alcohol is added, followed by 1.2 equivalents of p-toluene-sulfonic acid monohydrate (PTSA) or methanesulfonic acid (MsOH). The flask is then diluted with benzene 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 NaHCO3 and dried over MgSO4. The solvent is removed, and the washed material is diluted with cyclohexane and stored at 0 °C for 12 hours. The eluate is collected to obtain the desired modified amino acid ester.

[0256] General Method B: General Preparation of Pro-Beneficial Agent Compounds A round-bottom flask is charged with 1 equivalent of the modified amino acid ester precursor. To this flask, 1 equivalent of either cyclamen aldehyde or δ-damascone is added. 20 wt% of 4 Å molecular sieves are added to the fluid, and the mixture is stirred for 12 hours. The resulting mixture is filtered using a Pyrex 36060-30M Brand 36060 frit funnel and used directly.

[0257] Synthesis Example 1 Synthesis Example 1' was prepared as described in General Method A, except that 10.0 g of glycine, 24.8 g of 1-dodecanol, and 30.4 g of PTSA·H2O were used. Subsequently, the isolated solid of Synthesis Example 1' was mixed with cyclamen aldehyde (≥95%, Sigma-Aldrich, St. Louis, MO) as described in General Method B to obtain Synthesis Example 1. Independent fluid 1 is 1 apparently stable by 1H NMR for several months.

[0258] Synthesis Example 2 Synthesis Example 2' was prepared as described in General Method A, except that 10.0 g of L-alanine, 21.0 g of 1-dodecanol, and 25.6 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 2' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 2. Independent fluid 2 is 1 apparently stable by 1H NMR for several months.

[0259] Synthesis Example 3A Synthesis Example 3' was prepared as described in General Method A, except that 10.0 g of L-valine, 16.1 g of 1-dodecanol, and 19.5 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 3' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 3A. Independent fluid 3A is 1 apparently stable by 1H NMR for several months.

[0260] Synthesis Example 3B Synthesis Example 3' was prepared as described in General Method A, except that 10.0 g of L-valine, 16.1 g of 1-dodecanol, and 19.5 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 3' was mixed with δ-damascone as described in General Method B to obtain Synthesis Example 3B. Independent fluid 3B is 1 apparently stable by 1H NMR for several months.

[0261] Synthesis Example 4 Synthesis Example 4' was prepared as described in General Method A, except that 10.0 g of L-valine, 11.1 g of 1-octanol, and 19.5 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 4' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 4. The independent fluid 4 seems to be stable for several months by 1 1H NMR.

[0262] Synthesis Example 5 Synthesis Example 5' was prepared as described in General Method A, except that 10.0 g of L-valine, 11.1 g of 2-ethyl-1-hexanol, and 19.5 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 5' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 5. The independent fluid 5 seems to be stable for several months by 1 1H NMR.

[0263] Synthesis Example 6 Synthesis Example 6' was prepared as described in General Method A, except that 10.0 g of L-valine, 11.1 g of 4-octanol, and 19.5 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 6' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 6. The independent fluid 6 seems to be stable for several months by 1 1H NMR.

[0264] Synthesis Example 7 Synthesis Example 7' was prepared as described in General Method A, except that 10.0 g of L-valine, 10.5 g of 4-methylbenzyl alcohol, and 9.90 g of MsOH were used. Subsequently, the isolated fluid of Synthesis Example 7' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 7. The independent fluid 7 seems to be stable for several months by 1 1H NMR.

[0265] Synthesis Example 8 Synthesis Example 8' was prepared as described in General Method A, except that 10.0 g of L-valine, 18.3 g of 1-tetradecanol, and 19.5 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 8' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 8. The independent fluid 8 seems to be stable for several months by 1 1H NMR.

[0266] Synthesis Example 9 Synthesis Example 9' was prepared as described in General Method A, except that 10.0 g of L-valine, 20.8 g of 1-hexadecanol, and 19.5 g of PTSA·H2O were used. Subsequently, the isolated solid of Synthesis Example 9' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 9. The independent fluid 9 seems to be stable for several months by 1 1H NMR.

[0267] Synthesis Example 10 Synthesis Example 10' was prepared as described in General Method A, except that 10.0 g of L-valine, 23.0 g of 1-octadecanol, and 19.5 g of PTSA·H2O were used. Subsequently, the isolated solid of Synthesis Example 10' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 10. The independent fluid 10 seems to be stable for several months by 1 1H NMR.

[0268] Synthesis Example 11 Synthesis Example 11' was prepared as described in General Method A, except that 10.0 g of L-tryptophan, 9.1 g of 1-dodecanol, and 11.2 g of PTSA·H2O were used. Subsequently, the isolated solid of Synthesis Example 11' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 11. The independent fluid 11 seems to be stable for several months by 1 1H NMR.

[0269] Synthesis Example 12 Synthesis Example 12' was prepared as described in General Method A, except that 10.0 g of L-tyrosine, 10.3 g of 1-dodecanol, and 12.6 g of PTSA·H2O were used. Subsequently, the isolated solid of Synthesis Example 12' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 12. The independent fluid 12 is 1 apparently stable by 1H NMR for several months.

[0270] Synthesis Example 13 Synthesis Example 13 was prepared as described in General Method A, except that 10.0 g of L-aspartic acid, 28 g of 1-dodecanol corresponding to 2 equivalents, and 17.2 g of PTSA·H2O were used. Subsequently, the isolated solid of Synthesis Example 13' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 13. The independent fluid 13 is 1 apparently stable by 1H NMR for several months.

[0271] Synthesis Example 14 Synthesis Example 14 was prepared as described in General Method A, except that 10.0 g of L-methionine, 12.5 g of 1-dodecanol, and 15.3 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 14' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 14. The independent fluid 14 is 1 apparently stable by 1H NMR for several months.

[0272] Synthesis Example 15 Synthesis Example 15' was prepared as described in General Method A, except that 10.0 g of L-phenylalanine, 11.3 g of 1-dodecanol, and 13.8 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 15' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 15. The independent fluid 15 is 1It seems to be stable for several months by 1H NMR.

[0273] Synthesis Example 16 Synthesis Example 16' was prepared as described in General Method A, except that 10.0 g of L-isoleucine, 14.2 g of 1-dodecanol, and 17.4 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 16' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 16. The independent fluid 16 1 It seems to be stable for several months by 1H NMR.

[0274] Synthesis Example 17 Synthesis Example 17' was prepared as described in General Method A, except that 10.0 g of L-leucine, 14.2 g of 1-dodecanol, and 17.4 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 17' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 17. The independent fluid 17 1 It seems to be stable for several months by 1H NMR.

[0275] Synthesis Example 18 Synthesis Example 18' was prepared as described in General Method A, except that 10.0 g of L-phenylalanine, 11.4 g of C10PO1, and 13.8 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 18' was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 18. The independent fluid 18 1 It seems to be stable for several months by 1H NMR.

[0276] Synthesis Example 19 Synthesis Example 19’ was prepared as described in General Method A, except that 10.0 g of L-phenylalanine, 11.3 g of 2-dodecanol, and 13.8 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 19’ was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 19. The independent fluid 19 seems to be stable for several months by 1 1H NMR.

[0277] Synthesis Example 20 Synthesis Example 20’ was prepared as described in General Method A, except that 10.0 g of L-phenylalanine, 11.6 g of NEODOL 123, and 13.8 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 20’ was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 20. The independent fluid 20 seems to be stable for several months by 1 1H NMR.

[0278] Synthesis Example 21 Synthesis Example 21’ was prepared as described in General Method A, except that 10.0 g of L-phenylalanine, 11.6 g of ISALCHEM 123, and 13.8 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 21’ was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 21. The independent fluid 21 seems to be stable for several months by 1 1H NMR.

[0279] Synthesis Example 22 Synthesis Example 22’ was prepared as described in General Method A, except that 10.0 g of L-phenylalanine, 8.5 g of citronellol, and 13.8 g of PTSA·H2O were used. Subsequently, the isolated fluid of Synthesis Example 22’ was mixed with cyclamen aldehyde as described in General Method B to obtain Synthesis Example 22. The independent fluid 22 seems to be stable for several months by 1 1H NMR.

[0280] Synthesis Example 23 Method A: A stirred suspension of dodecylamine (5 g, 27 mmol) and L-phenylalanine (2.2 g, 13 mmol) in tert-amyl methyl ether (TAME, 50 mL) was heated to reflux using a Dean-Stark apparatus, and 1 equivalent of B(OCH2CF 33 , 8.3 g, 27 mmol) was added through the Dean-Stark apparatus. A West condenser was attached, and the reaction mixture was stirred under N2 for 24 hours. After completion, the reaction mixture was concentrated in vacuo and dry-packed onto silica gel for column chromatography. After purification, 23’ was obtained as a powdery white solid.

[0281] Method B: As described in Method A above, 1 equivalent of Ti(OiPr)4 was used instead of B(OCH2CF3)3.

[0282] Subsequently, the isolated solid of Synthesis Example 23’ was mixed with δ-damascone as described in General Method B, and the mixture was diluted with 10 wt% EtOH to obtain Synthesis Example 23. The independent fluid 23 appears to be 1 stable by 1H NMR for several months.

[0283] Synthesis Example 24 Synthesis Example 24’ was obtained from AStatEch, Inc (Bristol, PA, USA). Subsequently, Synthesis Example 24’ was mixed with cyclamen aldehyde and 10 wt% EtOH as described in General Method B to obtain Synthesis Example 24. The independent fluid 24 appears to be 1 stable by 1H NMR for several months.

[0284] Synthesis Example 25 To produce Synthesis Example 25, the following procedure can be followed. Phenylalanine is combined with an excess of trisaminoborane derived from N-methyldodecylamine (which can be prepared by treating BF3 dissolved in ether with a C6H6 solution of a secondary amine in the presence of a Grignard reagent. See Angewandte Chemie (1956), 68, 619). The mixture is stirred in MeCN (0.5 M) at 21 °C for 12 h. When complete, the mixture is diluted with CH2Cl2 and 1 equivalent of water. Amberlite IRA-743 and Amberlyst A-26(OH) are added to the mixture and stirred for 30 min. The combined mixture is dried over MgSO4 and filtered. The filtrate is reduced under reduced pressure and purified by column chromatography to give compound 25’. The isolated Synthesis Example 25’ is mixed with cyclamen aldehyde as described in General Method B to give Synthesis Example 25.

[0285] Synthesis Example 26 To produce Synthesis Example 26, the following procedure can be followed. Compound 26’ can be obtained by repeating the preparation of compound 25’ using dibutylamine instead of N-methyldodecylamine. The isolated Synthesis Example 26’ is mixed with cyclamen aldehyde as described in General Method B to give Synthesis Example 26.

[0286] Synthesis Example 27 To produce Synthesis Example 27, the following procedure can be followed. Compound 27’ can be obtained by repeating the preparation of compound 25’ using bis(2-ethylhexyl)amine instead of N-methyldodecylamine. The isolated Synthesis Example 27’ is mixed with cyclamen aldehyde as described in General Method B to give Synthesis Example 27.

[0287] Structure of the synthesis examples. Table D below shows the structures of Synthesis Examples 1-27, as well as their precursor compounds (indicated by ’).

[0288] Table D includes Comparative Synthesis Example A and a siloxane-based (Si-) pro-fragrance containing an imine bond. Table D further includes Comparative Synthesis Examples B and C, which are esterified amino acids derived from materials outside the scope of the present invention. That is, the length of the hydrophobic substance is relatively short (1 or 2 carbons each). The comparative examples are marked with an asterisk ( * ).

[0289]

Table 5-1

[0290]

Table 5-2

[0291]

Table 5-3

[0292]

Table 5-4

[0293]

Table 5-5

[0294] In the following performance examples and stability examples, the pro-beneficial agent precursor compounds (e.g., amino acid ester molecules) and the indicated fragrance raw materials are mixed substantially according to procedures consistent with the methods found in the above test method section ("Preparation of the Premix Fluid"). Despite the different preparation methods between the synthesis examples and the performance and stability examples (e.g., made with different PRMs), the inputs and outputs for the pro-beneficial agent compounds are substantially the same.

[0295] Performance Examples In the following Performance Examples 1-14, treatment compositions comprising neat essential oil, or a pro-benefit agent compound according to the present disclosure (e.g., based on a modified amino acid ester), or a premix emulsion comprising a comparative silicone polymer, are compared via a treatment cycle in an automatic washing machine according to the fabric treatment method described above. After treatment, the fabric is tested for headspace analysis according to the test methods provided above. The following data demonstrate the benefits provided by hydrophobically modified amino acid esters and their interactions with the benefit agents via imines or 1,4-adducts in the delivery of the benefit agents.

[0296] Performance Example 1. Application in a liquid fabric enhancer having a series of modified amino acid esters.

[0297] 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 were provided to the precursor amino acids as described above and then formulated into a test fabric enhancer / softener composition prepared as provided in the test method above. Test fabrics were prepared, washed, and tested for headspace analysis on the fabric according to the test methods described above.

[0298] For the rows labeled "Synthesis Example 1", etc. in both Table 1 and subsequent tables, the samples were prepared substantially according to the methods and precursors provided in the listed synthesis examples, but were prepared using the benefit agent materials listed in the performance table (in equimolar concentration with the precursor modified amino acid ester), not just cyclamen aldehyde or delta-damascone, and formulated as a premix fluid as detailed above.

[0299] The results of the above headspace analysis fabric tests are shown in Table 1 below.

[0300]

Table 6

[0301] As shown in Table 1, the hydrophobically modified amino acid esters 1-3 provided an improvement in the total headspace over the neat raw materials.

[0302] Furthermore, materials containing amino acid side groups 2 and 3 showed an increase in the total headspace over Synthesis Example 1. Synthesis Example 3 based on the amino acid valine had the highest total headspace with more favorable interactions for the sterically hindered beneficial agents, namely, florarozone and presicymon B.

[0303] Performance Example 2. Comparative example of silicone pro-fragrance vs. modified amino acid ester.

[0304] This example compares the relative performance of the pro-beneficial agent compounds disclosed herein to an industrially comparable silicone-based pro-fragrance. Both contain fragrance fragments linked by an imine bond.

[0305] The tests are conducted substantially the same as in Performance Example 1 using the beneficial agents and synthesis examples provided in Table 2 below. Similar to Performance Example 1, the profragrance silicone polymers are made using not only cyclamen aldehyde but also the listed beneficial agents and react in the form of a premix emulsion as described in the above method.

[0306] The results of the headspace analysis on the fabric are shown in Table 2.

[0307]

Table 7

[0308] As shown in Table 2, Comparative Synthesis Example A and Synthesis Example 3 provided a higher total headspace than the neat raw materials. Both Comparative Synthesis Example A and Synthesis Example 3 act via a similar imine mechanism and are thought to release the beneficial agent upon subsequent hydrolysis on the fabric. Synthesis Example 3 composed of natural materials provided the highest total headspace with respect to the described test method.

[0309] Performance Example 3. Preferred structure of the hydrophobic substance of the modified valine ester when delivering a beneficial agent.

[0310] To evaluate the performance impact of the Q group in Formula 1 on the delivery of the beneficial agent, a series of 8-carbon alcohols were attached to the valine amino acid. The tests were conducted in the same manner as described above in the form of a liquid fabric conditioner.

[0311] The structure of the hydrophobic substance / Q group and the logP values for each of the tested synthetic examples are provided in Table 3A below. The pound symbol / hash tag (#) represents the point of attachment of the ester group to the oxygen.

[0312] [Table 8]

[0313] The results of the headspace analysis of the above fabric are provided in Table 3B (at the 24-hour time point), and the results from the independent tests of Synthetic Examples 4 and 7 are provided in Table 3C.

[0314] [Table 9]

[0315] [Table 10]

[0316] This performance test emphasizes that the structural connectivity of the alcohol hydrophobic substance significantly affects the delivery of the beneficial agent. The most preferred order based on the data illustrated in Table 3B, at the 24-hour headspace time point, is as follows. Synthetic Example 4 > Synthetic Example 5 >> Synthetic Example 6 >> Synthetic Example 7 > Pure raw material.

[0317] Linear hydrophobic substances (e.g., Synthesis Example 4) are more preferred than branched hydrophobic substances (Synthesis Examples 5 and / or 6). Further, the terminal alcohol of Synthesis Example 4 is more preferred than the internal alcohol of Synthesis Example 6. Finally, the aryl-containing hydrophobic substance in Synthesis Example 7 generally appears to provide a narrower profit than the pure raw material after 24 hours.

[0318] To help illustrate the dynamic range of beneficial agent affinity and release lifetime obtained with different hydrophobic substances, a second independent test was conducted and tabulated in Table 3C. The independent test measured the headspace at the 72-hour time point for Synthesis Examples 4 and 7. Referring to the results in Table 3B, there is a priority order of Synthesis Example 4 > Synthesis Example 7 > pure raw material. Further examination revealed that Synthesis Example 4 had a higher count of methyl nonyl acetaldehyde but a lower count of fluralaner than Synthesis Example 7. This can result in different olfactory experiences in consumer products. Without being bound by theory, the difference in beneficial agent affinity may be partially influenced by the structural conformation of the two molecules, such as net molecular interactions via either dipole-dipole interactions with the modified amino acid backbone or potentially aryl-aryl (π-π) interactions.

[0319] Performance Example 4. The preferred hydrophobic alcohol chain length is on the amino acid core.

[0320] As shown in Performance Example 3, the hydrophobic substance / Q group in Formula 1 plays an important role in the delivery efficiency of the beneficial agent. Subsequently, the most preferred chain length of the hydrophobic substance / Q group was investigated with respect to beneficial agent delivery. A series of linear alcohols used to make the hydrophobic substance / Q group were selected as the most preferred based on the above results. Table 4A shows the number of carbon atoms in the linear hydrophobic substances of each example.

[0321]

Table 11

[0322] Provide the results of the headspace analysis on the fabric to Table 4B.

[0323]

Table 12

[0324] As shown in Table 4B, the Q group defined by Formula 1 having at least 8 straight-chain carbon atoms appears to be required to obtain the highest profit. In the newly prepared samples, the most preferred carbon length is represented by Synthesis Example 3 and Synthesis Example 4. Further, each hydrophobic substance in the carbon range of 8 to 18 provides a performance advantage when compared with Comparative Example B or C (one or two carbons respectively).

[0325] Additional internal tests (results not shown here) indicate that adding additional carbon atoms (e.g., 20 or more) does not significantly improve performance. Therefore, for reasons of mass efficiency, it may be preferable to use up to 18 carbons in the hydrophobic substance. In addition, using hydrophobic substances having additional carbon (e.g., 20 or more) appears to present processing difficulties, which may require the addition of additional processing aids such as solvents, which results in extra costs without adding additional performance benefits. The lower carbon scaffolds provide advantages over undiluted fragrances under current methods, but subsequent internal stability studies indicate that, unlike longer carbon chain scaffolds, this moderate advantage can be lost over time.

[0326] Performance Example 5. Effect of amino acid side groups on imine formation and performance through rinsing.

[0327] To investigate the effect of amino acid side groups on performance, further experiments were conducted. Various amino acid side groups with different functionalities and substituents were selected to investigate the most preferred structural variants. The amino acid side groups tested are shown in Table 5A. The pound symbol / hash tag (#) represents the point of attachment to the central carbon of the amino acid.

[0328]

Table 13

[0329] Provide the results of the headspace analysis on the fabric to Table 5B.

[0330]

Table 14

[0331] Each of the synthesis examples in Table 5B shows an improved headspace compared to the pure raw materials. Among the series, synthesis example 3 based on valine has the highest total headspace.

[0332] Interestingly, synthesis example 13 with two hydrophobic substances did not result in an overall improvement over synthesis example 3. This suggests that additional hydrophobic substances (e.g., two or more) are not required to efficiently deliver the beneficial agent.

[0333] Furthermore, the ratio between the individual beneficial agents across the synthesis examples is approximately conserved, thereby suggesting that the imine is slightly affected by the amino acid R groups.

[0334] Performance Example 6. Selected investigation of hydrophobic amino acid side groups for beneficial delivery in liquid fabric enhancer formulations.

[0335] A subsection of hydrophobic amino acids is investigated for their ability to deliver beneficial agents. Newly prepared samples in the liquid fabric enhancer are tested using the accord of the beneficial agent. The tested amino acid side groups are shown in Table 6A. The pound symbol / hash tag (#) represents the point of attachment to the central carbon of the amino acid.

[0336]

Table 15

[0337] Provide the results of the headspace analysis on the fabric to Table 6B.

[0338]

Table 16

[0339] As illustrated in Table 6B, all of the tested synthesis examples resulted in an improvement in the headspace over the pure raw materials. Among these, Synthesis Examples 3 and 15 are both slightly superior to Synthesis Example 16. Similar ratios in the individual beneficial agents were observed across the synthesis examples.

[0340] Performance Example 7. Influence of single-carbon elongation of amino acid side groups on the performance of beneficial agents in a liquid fabric enhancer.

[0341] Of interest is the investigation of the steric requirements for imine formation and the relative performance of such constructs through rinsing. Furthermore, the influence of a single carbon atom can provide insights into the hydrophobicity due to the amino acid side group and the degree of adhesion aid. To investigate this phenomenon, the amino acid cores of valine and leucine (including an extra carbon spacer) are selected as comparative examples.

[0342] The tested amino acid side groups are shown in Table 7A. The pound symbol / hash tag (#) represents the point of attachment to the central carbon of the amino acid.

[0343]

Table 17

[0344] The results of the headspace analysis on the fabric are provided in Table 7B.

[0345]

Table 18

[0346] Table 7B illustrates the difference in one carbon atom on the amino acid side group. The performance results indicate that both materials provide significant benefits over the pure raw materials. Furthermore, the smaller side group shown in Synthesis Example 3 appears to be more favorable than the side group of Synthesis Example 17.

[0347] Performance Example 8. Performance across various fabric types.

[0348] In addition to the cotton terry exemplified in each of the performance examples, there is an interest in examining the performance across a series of fabric types that closely represent the consumer's washing load. The washing conditions are the same as those described in the above method, except for using the following fabric loads: Five 8×8 swatches of each of the following fabric types were used: woven cotton terry (100% fiber content), weft-knit cotton knit (100% fiber content), plain-woven polyester / cotton (65:35 fiber content), weft-knit polyester (100% fiber content), woven satin cotton / spandex (98:2 fiber content), and the fabrics were purchased from WFK Testgewebe GmbH, Christenfeld 10, D-41379 Bruggen, Deutschland.

[0349] The results of the headspace analysis on the fabric are provided in Table 8A.

[0350]

Table 19

[0351] Table 8A shows that Synthesis Example 3 provides benefits across each of the fabric types over the pure raw materials. Polyester showed the largest delta between the raw material and Synthesis Example 3. Furthermore, the spandex composition resulted in the smallest delta between Synthesis Example 3 and the pure raw material based on the total headspace. In mixed washing applications, the inventors observe that the distribution ratio of the individual benefit agents distributed across the fabric is closer to being more uniform.

[0352] Performance Example 9. Multi-cycle effect of modified amino acid esters in liquid fabric softeners.

[0353] Multi-cycle washing tests are of interest because they represent continuous use of the product by the consumer. In this study, fabrics are subjected to multiple washing cycles as described in the above test method and Performance Example 8, with a 24-hour rest day between each repeated fabric wash. A proprietary beneficial agent compound as described below is included in each cycle as part of the liquid fabric softener composition.

[0354] The results of headspace analysis on the fabric are provided in Table 9A.

[0355] [Table 20]

[0356] From the repeated treatment according to Synthesis Example 3, a multi-cycle effect is observed across several fabrics (see Table 9A). The greatest increase in performance due to the multi-cycle benefit was observed for poly-cotton and spandex.

[0357] Performance Example 10. Use and benefits of Synthesis Example 1 in dry particulate formulations First, esterified glycine is reacted with cyclamen aldehyde as described above to obtain Synthesis Example 1. In this example, the formulation of the material is prepared for dry formed particle use (e.g., a pastille containing polyethylene glycol as a carrier, similar in size and shape to those sold by Procter & Gamble Company as DOWNY UNSTOPABLES™). The formulation of each leg particle is provided in Table 10A, where Synthesis Example 1 is introduced as a premix fluid as detailed above. The amounts are shown as weight % relative to the weight of the composition.

[0358] [Table 21]

[0359] In the following examples, test fabric pastille compositions are provided with fragrance raw materials of equimolar concentration as prepared in the above test method. Test fabrics are prepared, washed, and tested for headspace analysis on the fabric according to the above test method. The results are provided in Table 10B.

[0360] [Table 22]

[0361] As shown in Table 10B, Synthesis Example 1 in the dry particle formulation shows advantages over the pure raw material through rinsing and the dryer.

[0362] Performance Example 11. Performance Evaluation in Dry Particle Formulation To investigate the range of suitable amino acid cores, a series of cyclamen aldehyde materials are formulated into dry pastille formulations. It is expected that certain amino acid side groups may be more favorable than others when delivering a greater amount of beneficial agent in the dry particle formulation. Glycine, alanine, and valine were considered as the amino acid for each core.

[0363] The results of the headspace analysis on the fabric are provided in Table 11A.

[0364] [Table 23]

[0365] As shown in Table 11A, a series of hydrophobically modified amino acid esters are examined in dry particle form. Each of the materials provides a greater benefit than the pure raw material. Synthesis Example 1 provides the largest headspace, followed by Synthesis Example 2 and then Synthesis Example 3.

[0366] This trend suggests that the choice of amino acid side groups is less important when the material is formulated in a dry form, such as the solid particles tested here, as compared to the liquid / aqueous form. See, for example, Performance Examples 3, 4, 5, and 7 above.

[0367] That being said, the premix composition may be useful when formulating the material in a dry form such that the precursor compound and the beneficial agent can associate in a liquid.

[0368] Furthermore, although showing slightly lower performance in the table above, the valine-based core may be preferred for reasons of stability, for example, due to its tendency to remain unpolymerized.

[0369] Performance Example 12. Performance evaluation in a detergent composition.

[0370] The liquid detergent described in the above test method is combined with a modified amino acid ester containing δ-damascon as the beneficial agent.

[0371] The results of headspace analysis on the fabric are provided in Table 12A.

[0372]

Table 24

[0373] The results in Table 12A show that Synthesis Example 3B provides an improvement in the beneficial agent in the headspace compared to the pure raw material when used in a liquid laundry detergent.

[0374] Performance Example 13. Softener level and performance benefits.

[0375] To investigate the potential synergistic effect between the pro-beneficial agent compound according to the present disclosure and the cationic softener in the liquid fabric enhancer formulation, the concentration of the cationic softener (diester quaternary ammonium, i.e., N,N-di(tallow oil oxyethyl)-N,N-dimethylammonium) is varied. As described in the preparation of the above test fabric enhancer / softener composition, three different diester quaternary ammonium concentrations (4 wt%, 7.3 wt%, and 12 wt%) are formulated.

[0376] The results of the headspace analysis on the fabric are provided in Table 13A.

[0377]

Table 25

[0378] As shown in Table 13A, the performance of Synthesis Example 3 is affected by the concentration of the diester quaternary ammonium. The best performance is obtained when the softener exceeds 4% under the described test conditions.

[0379] Performance Example 14. Combination of undiluted sesame oil and pro-beneficial promoting amino acid ester when delivering the beneficial agent to the fabric.

[0380] Undiluted sesame oil is common in fabric treatment compositions. The relationship between sesame oil and the pro-beneficial agent compound (e.g., modified amino acid ester) is examined at three concentrations in the range of 2% pure oil to 10% pure oil.

[0381] The sesame oil is a combination of fragrance raw materials that does not contain aldehydes or ketones delivered by amino acid-based beneficial accelerators. Specifically, the undiluted sesame oil contains, based on the weight of the undiluted sesame oil, 10% by weight of geraniol, 20% by weight of citronellol, 20% by weight of acetophon, 30% by weight of limonene, and 20% by weight of 1,1-dimethoxydodecane. In particular, the undiluted sesame oil contains, among other things, fragrance types (e.g., alcohols, nitriles, and / or esters) that may not contribute to the formation of imine bonds with modified amino acids according to the present disclosure, since there are no aldehydes and ketones.

[0382] Table 14A provides the results of headspace analysis on the fabric for aldehydes and / or ketones delivered by the pro-beneficial agent compound.

[0383]

Table 26

[0384] Table 14A illustrates that the continuous addition of undiluted sesame oil to the fabric softening formulation has a correlation with the amount of beneficial agent delivered by Synthesis Example 3. Without being bound by theory, hydrophobic substances (e.g., undiluted sesame oil and hydrophobic modified amino acids) tend to associate in the aqueous product matrix and / or the cleaning solution, thereby protecting at least a portion of the pro-beneficial agent compound from water, reducing hydrolysis, and improving stability.

[0385] Performance Example 15. Testing of alcohol performance from primary, secondary, and alkoxylated alcohols.

[0386] The flexibility in the alcohol feedstock is attractive for commercialization. Further, the chemical reactivity of esters, the kinetics of esterification, and hydrolysis are affected based on the structural arrangement. An investigation is conducted regarding whether a difference in performance is observed among Q groups containing primary, secondary, and alkoxylated alcohols having an average of 12 carbon atoms.

[0387] The structure of the hydrophobic substance / Q group for each of the tested synthesis examples is provided in Table 15A below. The pond symbol / hash tag (#) represents the point of attachment to the oxygen of the ester group.

[0388] [Table 27]

[0389] The fabric is treated with the composition, and the results of headspace analysis on the fabric are provided in Table 15B.

[0390] [Table 28]

[0391] The results in Table 15B show the performance across a series of Q groups with primary, secondary, or alkoxylated alcohols. Each of the synthetic materials offers advantages over undiluted oil. Within the series, Synthesis Examples 18 and 19 had improved performance compared to Synthesis Example 15. Further, without being bound by theory, Synthesis Examples 18 and 19, being composed of secondary alcohols, would have improved hydrolysis stability.

[0392] Performance Example 16. Testing of secondary amides in the delivery of beneficial agents in a fabric strengthening agent / softening agent composition.

[0393] The fabric strengthening agent / softening agent composition described in the above test method is combined with a modified amino acid that constitutes a secondary amide containing δ-damascon as the beneficial agent. The fabric is treated with the composition, and the results of headspace analysis on the fabric are provided in Table 16.

[0394] [Table 29]

[0395] The results in Table 16 show that when Synthesis Example 23 is used in the fabric strengthening agent / softening agent composition, it brings about an improvement in the beneficial agent in the headspace compared to the pure raw materials.

[0396] Performance Example 17. Performance evaluation of tertiary amides in the fabric strengthening agent / softening agent composition The fabric strengthening agent / softening agent composition described in the above test method is combined with a modified amino acid constituting a tertiary amide containing an aldehyde beneficial agent. The fabric is treated with the composition, and the results of headspace analysis on the fabric are provided in Table 17.

[0397]

Table 30

[0398] The results in Table 17 show that when Synthesis Example 23 is used in the fabric strengthening agent / softening agent composition, it brings about an improvement in the beneficial agent in the headspace compared to the pure raw materials.

[0399] Stability Example In Stability Example 1, a modified amino acid ester premix fluid is formulated into the treatment composition, and the color stability during storage is recorded.

[0400] Stability Example 1. Color stability of modified amino acid esters.

[0401] Pro-beneficial modified amino acid esters, specifically premixes in fluid form, and related fabric softening agent products formed from such premix fluids are prepared. Color measurements of fabric softening agent products containing the modified amino acid ester premix fluid of Synthesis Example 3 are measured as described in the above test method. A lower ΔE t value indicates less color change compared to the fresh product.

[0402] The aldehyde-containing beneficial agent is formulated at 0.2% by weight of the total treatment composition (the aldehyde composition is as follows: 10% by weight of methyl nonyl acetaldehyde, 40% by weight of P.T. businal, 20% by weight of precycle mon B, and 30% by weight of florarozone). Similar to the previous examples, the synthetic examples are made using the listed aldehydes rather than simply cyclamen aldehyde or δ-damascone, and it is understood to react with the beneficial agent in the form of a premix fluid as detailed above. The comparative composition is made using the KF-8003 silicone premix emulsion and the same aldehydes as above (for example, Comparative Example A).

[0403] The color stability of the fabric softener product during 4-week storage is evaluated by the color change of the composition test method provided above. The results are shown in Table 1 below.

[0404]

Table 31

[0405] As shown in Table 1S, the product formulated using Synthetic Example 3 containing a modified amino acid ester in combination with the beneficial agent fragment shows a relatively low ΔE t indicating that there is relatively little color change compared to the product formed using pure raw materials.

[0406] Furthermore, the product formulated using Synthetic Example 3 shows a relatively low ΔE o after storage at 40 t ℃ compared to the product formulated using the imine-containing silicone Comparative Synthetic Example A. Without being bound by theory, the imine constructed in Synthetic Example 3 is thought to reduce the overall strength from the beneficial agent residue. Additionally or alternatively, the nature of the bonds in the exemplary modified amino acid ester that results in Synthetic Example 3 having improved color stability over time may be due, in part, to reduced gelation compared to the gelation that may be more predominant in Comparative Synthetic Example A.

[0407] The dimensions and values disclosed in this specification are not to 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 to be taken to mean "about 40 mm".

[0408] All documents cited in this specification, including any patents or patent applications that are cross-referenced or related, and any patent application or patent for which this application claims priority or the benefit thereof, are hereby incorporated by reference in their entirety, unless expressly excluded or limited. The citation of any document is not to be construed as an admission that it is prior art to any invention disclosed or claimed in this specification, or that it alone or in any combination with any other reference teaches, suggests, or discloses any such invention. Further, in the event 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 the term in this document shall apply.

[0409] Although specific embodiments of the invention have been illustrated and described, it will be apparent 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. Accordingly, it is intended that all such changes and modifications within the scope of the invention be covered by the appended claims. This specification discloses the following invention. 1. A pro-beneficial agent compound, wherein the compound is characterized by a structure according to formula II,

Chemical formula

Claims

1. A treatment composition comprising an auxiliary component and a probiotic compound, wherein the probiotic compound is characterized by the structure according to Formula II, 【Chemical 1】 In the formula, G is selected from -O- or -N(R ３ ), R ３ When present, is -H or -CH ２ CH(OCH ２ CH ３ ), ２ selected from In the formula, Q is an alkyl group having 8 to 18 carbon atoms, -CH ２ C ６ H ４ CH ３ , -CH2CH2C6H5 or -CH(CH ３ )CH ２ O(CH ２ ), ９ CH ３ selected from In the formula, the subscript m is 1, In the formula, R １ is a side group of a protein - constituting amino acid, R ２ is -H, In the formula, Z is a fragment of a fragrance raw material containing an aldehyde moiety and / or a ketone moiety, In the formula, ＊＊ represents the linking bond between the nitrogen atom and the carbon atom of the Z group, and the linking bond is one of the following: (a) a double bond, thereby forming an imine bond, or (b) when the fragrance raw material contains an alpha - beta unsaturated carbonyl - containing moiety that is an aldehyde moiety or a ketone moiety, a single bond formed from 1,4 - addition, Here, ＊＊ when represents a single bond, the nitrogen atom is further bonded to hydrogen (-H), The treatment composition is a consumer product selected from a fabric care composition, a hard surface cleaner composition, a dish care composition, a hair care composition, or a body cleansing composition, the treatment composition.

2. R １ has the structure of the side group of the protein constituent amino acid selected from the group consisting of valine, phenylalanine, leucine, and isoleucine, the treatment composition according to claim 1.

3. Q is an alkyl group containing 8 to 14 carbon atoms, the treatment composition according to claim 1.

4. The processing composition according to claim 1, wherein the perfume raw material is selected from the group consisting of methyl nonyl acetaldehyde, benzaldehyde, floralozone, isocyclocitral, triplal (ligustral), presilkeemon B, lilial, decyl aldehyde, undecylenic aldehyde, cyclamen homologue aldehyde, cyclamen aldehyde, Dupical, oncidar, adoxal, melonal, calypsone, anisaldehyde, heliotropin, cuminaldehyde, scentenal, 3,6-dimethylcyclohex-3-ene-1-carbaldehyde, satenal, 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, butyl cinnamic aldehyde, limoneral, amyl cinnamic aldehyde, hexyl cinnamic aldehyde, citronellal, citral, cis-3-hexen-1-al, neral, 4-(4-methoxyphenyl)butan-2-one, 1-naphthalen-2-ylethanone, nectaryl, trimofix O, fluramon, delta-damascone, beta-damascone, alpha-damascone, methyl ionone, 2-hexylcyclopent-2-en-1-one, galvascon, and mixtures thereof.

5. The treatment composition according to claim 1, wherein the auxiliary component comprises one or more of a surfactant, a conditioning active substance, an adhesion aid, a rheology modifier or structuring agent, an antioxidant, a bleaching system, a stabilizer, a builder, a chelating agent, a migration inhibitor, a dispersant, an enzyme, an enzyme stabilizer, a catalytic metal complex, a polymeric dispersant, a soil and stain removal / redeposition inhibitor, a brightening agent, a foam inhibitor, a silicone, a hue agent, an aesthetic dye, a neat fragrance, a fragrance delivery system, a structure elasticizer, a carrier, a hydrotrope, a processing aid, an antiagglomerant, a coating, a formaldehyde scavenger, and / or a pigment.

6. The treatment composition according to claim 1, wherein the auxiliary component comprises a conditioning active substance.

7. The treatment composition according to claim 1, wherein the treatment composition further comprises a neat fragrance.

8. The treatment composition according to claim 1, which is in the form of a liquid composition, a granular composition, a hydrocolloid, a single-compartment pouch, a multi-compartment pouch, a soluble sheet, a pastille or bead, a fibrous article, a tablet, a stick, a bar, a flake, a foam / mousse, or a non-woven sheet.

9. The treatment composition according to claim 1, wherein the pro-beneficial agent compound is present in the treatment composition at a concentration of 0.001% to 30% by weight of the treatment composition.

10. A method of treating an article or surface, comprising treating the article or surface with the treatment composition according to claim 1, optionally in the presence of water.

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