Compositions comprising adamantyl ester-containing compounds

Abstract

Compositions, such as consumer products and / or fragrance compositions, comprising an adamantyl ester-containing compound.

Description

TECHNICAL FIELD

[0001] The present disclosure relates to compositions, such as consumer products and / or fragrance compositions, that include adamantyl ester-containing perfumes. The present disclosure also relates to methods of making and using such compositions. BACKGROUND

[0002] Consumer products that incorporate pleasing scents, such as cleaning products, soaps, detergents, fabric refreshers, antiperspirants, air fresheners, and fine fragrances, are always in demand. One popular fragrance material that has traditionally been used in and associated with consumer products is octahydro-tetramethyl-acetophenone, also known as 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthyl)ethanone, also known as OTNE. In instances where OTNE is not available, there is a need for alternative fragrance materials that have similar scent characteristics. Thus, there is a continuing need for new fragrance materials that can be used in consumer products, compositions, and related methods. SUMMARY

[0003] The present disclosure relates to compositions, such as consumer products and / or fragrance compositions, that include adamantyl ester-containing compounds, such as 2-methyl-2-adamantyl acetate, 2-adamantyl acetate, or 2-adamantyl propionate.

[0004] For example, the present disclosure relates to a consumer product comprising: a first fragrance material that is an adamantyl ester-containing compound, wherein the first fragrance material is present in an amount of at least 0.0005% by weight of the consumer product composition; and a treatment adjunct.

[0005] The present disclosure also relates to a method of making a consumer product, the method comprising the step of combining a first fragrance material with a treatment adjunct or a substrate, wherein the first fragrance material is an adamantyl ester-containing compound.

[0006] The present disclosure also relates to a method of treating a surface or environment, the method comprising the step of providing an adamantyl ester-containing compound to the surface or environment.

[0007] The present disclosure also relates to the use of an adamantyl ester-containing compound in a consumer product, surface, or environment. DETAILED DESCRIPTION

[0008] The present disclosure relates to compositions, consumer products, and methods that include adamantyl ester-containing compounds as alternatives to OTNE. The adamantyl ester-containing G-C(O)-O-Q structured compounds detailed herein differ from previously known in the art and suggested as perfumes in at least one of two ways. The previously known compounds have an adamantyl group as part of the G group, or alternatively, the adamantyl group is part of the Q group, but more than one carbon of the adamantyl group is substituted. We are not aware of any known perfume compounds in which a single position substituted adamantyl group has been placed in the Q group. Thus, it was surprisingly discovered that these long overlooked materials are very useful fragrance materials, e.g., showing surprisingly high headspace properties. In addition to similar scent profiles as OTNE (i.e., having a cedar and amber note), the adamantyl ester-containing compounds have certain advantageous properties that can make them more attractive to consumer product manufacturers. For example, because the adamantyl ester-containing compounds described herein have a relatively higher headspace compared to OTNE, the adamantyl ester-containing compounds can even be more preferred by saving raw material costs, carbon footprint, and / or formulation space. Moreover, because the adamantyl ester contains an ester linkage, the adamantyl ester-containing compounds will also be expected to have improved biodegradability. Furthermore, the adamantyl ester-containing compounds detailed herein can also have improved oxidation resistance and better blooming (i.e., volatility).

[0009] Fragrance materials, compositions, consumer products, and related methods are discussed in more detail below.

[0010] As used herein, the articles “a” and “an” are understood to mean one or more of the items being described. As used herein, the terms “include,” “containing,” and “containing” are intended to be non-limiting. The compositions of the present disclosure can include, consist essentially of, or consist of the components of the present disclosure.

[0011] The term “substantially free of’ can be used herein. This means that the specified material is very small, not intentionally added to the composition to form part of that composition, or preferably the specified material is not present at analytically detectable levels. This means compositions including where the specified material is present only as an impurity in one of the other materials intentionally added. If present at all, the specified material can be present at a level of less than 1%, or less than 0.1%, or less than 0.01%, or even 0%, by weight of the composition.

[0012] As used herein, "consumer product" can include baby care, beauty care, fabric and home care, family care, feminine care, health care, food (including snacks), beverages, and / or premium fragrance products or devices generally intended to be used or consumed in a saleable form. Such products include, but are not limited to, diapers, bibs, wipes; products and / or methods relating to the treatment of hair (human, dog, and / or cat), including bleaching, coloring, dyeing, conditioning, shampooing, styling; deodorants and antiperspirants; personal cleansing; cosmetics; skin care, including the application of creams, lotions, and other topically applied products for consumer use (including premium fragrance products); and shaving products, products and / or methods relating to the treatment of fabrics, hard surfaces, and any other surfaces in the area of fabric and home care, including: air care (including air fresheners and scent delivery systems), car care, dishwashing, fabric conditioning (including softening and / or freshening), laundry detergency, laundry and rinse additive and / or care, hard surface cleaning and / or treatment (including floor and toilet bowl cleaners), and other cleaning for consumer or institutional use; products and / or methods relating to sanitary tissue, facial tissue, paper handkerchiefs, and / or paper towels; tampons, feminine napkins; products and / or methods relating to oral care, including toothpastes, tooth gels, tooth whitening, denture adhesives, tooth mousse; over-the-counter health care, including cough and cold remedies, pain relievers, RX drugs, pet health and nutrition; food products, including processed food products primarily intended for consumption between meals or as a meal accompaniment (non-limiting examples include potato chips, unfermented tortilla chips, popcorn, pretzels, corn chips, cereal bars, vegetable chips or crisps, snack mixes, party mixes, grain chips, snack crackers, cheese snacks, pork rinds, corn snacks, pellet snacks, extruded snacks, and bagel chips); beverages, including carbonated beverages, tea, flavored waters, and coffee; and water purification.

[0013] As used herein, the phrase "fabric care product" includes compositions and formulations designed for treating fabrics. Such compositions include, but are not limited to, laundry cleaning compositions and detergents, fabric softening compositions, fabric enhancing compositions, fabric freshening compositions, laundry prewash, laundry pretreatment, laundry additives, spray products, dry cleaning agents or compositions, laundry rinse additives, wash additives, post-rinse fabric treatment, ironing aids, unit dose formulations, delayed delivery formulations, detergents contained on or in a porous substrate or nonwoven sheet material, and other suitable forms that can be apparent to those skilled in the art in light of the teachings herein. Such compositions can be used as a laundry pretreatment, a laundry post-treatment, or can be added during the rinse cycle or wash cycle of a laundry operation.

[0014] All component or composition water levels are with respect to active portions of the component or composition, and do not include impurities that can be present in commercially available sources of such components or compositions, for example, residual solvents or by-products, including small amounts of degradation products that can form upon storage, unless otherwise specified.

[0015] All temperatures herein are in degrees Celsius (°C), unless otherwise indicated. All measurements herein are at 20 °C and at atmospheric pressure, unless otherwise specified.

[0016] In all embodiments of the present disclosure, all percentages are by weight of the total composition, unless specifically stated otherwise. All ratios are weight ratios, unless specifically stated otherwise.

[0017] It should be understood that every maximum numerical limitation given throughout this specification includes every lower numerical limitation, as if such lower numerical limitations were expressly written herein. Every minimum numerical limitation given throughout this specification will include every higher numerical limitation, as if such higher numerical limitations were expressly written herein. Every numerical range given throughout this specification will include every narrower numerical range that falls within such broader numerical range, as if such narrower numerical ranges were all expressly written herein.

[0018] Compounds containing adamantyl esters :

[0019] The compositions, products, and methods described herein include adamantyl ester-containing compounds. As described in greater detail below, it is believed that such materials can provide a pleasing fragrance (i.e., a similar fragrance profile to OTNE) to compositions and products, while also having certain advantageous properties, such as more pronounced fragrance throw, which can help to save raw material costs, carbon footprint, and / or formulation space.

[0020] As described herein, the specifically detailed adamantyl ester-containing compounds are referred to as (first) fragrance materials.

[0021] The basic structure of the specific adamantyl ester-containing compounds is G-C(O)-O-Q. G and Q are carbon-containing groups that are connected only through an ester linkage. Q includes a single adamantyl moiety, and only one carbon atom of the adamantyl moiety is substituted with something other than hydrogen. Thus, the compounds are selected from:

[0022] Formula 1, or

[0023] Formula 2, or

[0024] mixtures thereof.

[0025] For Formula 1 or Formula 2:

[0026] 1. R is hydrogen or a hydrocarbyl group;

[0027] 2. E contains only a single -CO2- moiety;

[0028] 3. the molecular formula is C 11+n H 16+2n-m O2,

[0029] wherein n is an integer from 1 to 7, preferably 1 to 5, more preferably 1 to 3, even more preferably 1 to 2; and

[0030] m is 0 or 2, and

[0031] wherein when m is 0, the molecule contains no carbon-carbon double bonds; and

[0032] wherein when m is 2, the molecule contains a single carbon-carbon double bond, and preferably the carbon-carbon double bond is directly bonded to the carbonyl carbon atom.

[0033] Non-limiting examples of adamantyl ester-containing compounds detailed herein include:

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063] As further described in the Examples section below, certain adamantyl ester-containing compounds of interest, such as but not limited to 2-methyl-2-adamantyl acetate, 2-adamantyl acetate, or 2-adamantyl propionate, are characterized by a scent profile similar to OTNE, as well as certain other desirable properties, including high headspace, which can make them desirable replacements for OTNE in consumer products.

[0064] Consumer product

[0065] The present disclosure relates to consumer products comprising adamantyl ester-containing compounds. Typically, the consumer product will also comprise a treatment adjunct. Additionally or alternatively, the consumer product can comprise an adamantyl ester-containing compound provided to a substrate.

[0066] The consumer product can take any suitable form. Preferably, the consumer product is a baby care product, a beauty care product, a fabric care product, a home care product, a household care product, a feminine care product, a health care product, a food product, a beverage product, a high quality fragrance product, or a combination thereof. The consumer product of the present disclosure can be a composition, a device, or a combination thereof that can be used in baby care, beauty care, fabric care, home care, household care, feminine care, health care, food, beverage, and / or high quality fragrance applications. For consumer health reasons, it can be preferred that the consumer product is not a tobacco-related product, such as a cigarette, an electronic cigarette, or a product intended to produce a tobacco-like odor (such as an aerosol).

[0067] The consumer product can preferably be a fabric care product and / or a home care product, wherein the home care product is selected from the group consisting of a hard surface cleaner, a dish care product, an air care product, or a combination thereof. The consumer product can be a cleaning and / or treatment product.

[0068] The consumer product can take any suitable form or combination of forms. For example, the consumer product can comprise a form selected from the group consisting of a liquid composition, a granular composition, a hydrocolloid, a single-compartment pouch, a multi-compartment pouch, a dissolvable sheet, a pastille or bead, a fibrous article, a tablet, a stick, a bar, a flake, a spray, a foam / mousse, a nonwoven sheet, a dispensing device, a cream, an absorbent article, a paste, an adhesive, an adhesive patch, or a mixture thereof. The consumer product can be a composition, such as a liquid composition, housed in a container, a dispensing device, or other suitable article.

[0069] The consumer product can comprise a first fragrance material that is a diamondoid- containing compound, wherein the first fragrance material is present in an amount of at least 0.0005% by weight of the consumer product; and a treatment adjunct.

[0070] The consumer product can comprise a first fragrance material (diamondoid-containing compound) in an amount of at least 0.0005%, preferably at least 0.001%, more preferably at least 0.01%, preferably at least 0.1%, preferably at least 0.5%, more preferably at least 1%, by weight of the consumer product. It is preferred that a minimum amount of the first fragrance material is present to deliver the desired olfactory performance.

[0071] The consumer product can comprise a first fragrance material (diamondoid-containing compound) in an amount of at most about 99%, preferably at most about 50%, preferably at most about 25%, more preferably at most about 10%, even more preferably at most about 5%, even more preferably at most about 1%, by weight of the consumer product. It can be preferred that a maximum amount or limit of the first fragrance material is present in order to include other adjuncts or fragrance materials.

[0072] The consumer product can comprise the first fragrance material (adamantyl ester containing compound) in an amount of from about 0.01% to about 99%, preferably from about 0.1% to about 50%, more preferably from about 0.5% to about 10%, more preferably from about 1% to about 5%, by weight of the consumer product.

[0073] The consumer product can comprise the first fragrance material (adamantyl ester containing compound) and a second fragrance material selected from the group consisting of any fragrance material suitable for the intended product or end use, wherein the total fragrance material consists of at least 10%, more preferably at least 20%, more preferably at least 30%, more preferably at least 40%, more preferably at least 50%, more preferably at least 60%, more preferably at least 70%, more preferably at least 80%, more preferably at least 90%, more preferably at least 95% of biodegradable material. The term "biodegradable" is defined herein as chemical lysis, disintegration or digestion of the biodegradable perfume by bacterial or other biological means at a rate higher than 50% according to the OECD 301 C test method which defines the ready biodegradability of a material. In this test, the biodegradable perfume is suspended in a phosphate buffer medium containing an active sludge inoculum and the consumption of oxygen and / or the formation of carbon dioxide is measured by electrolytic respirometry. The test substance is the sole source of carbon and energy and under aerobic conditions, the microorganisms metabolize the organic substance producing CO2 as the end product.

[0074] For example, the consumer product can comprise: a first fragrance material which is an adamantyl ester containing compound; an optional second fragrance material selected from the group of OTNE, 4-methyl-8-methylene-tricyclo[3.3.1.13 3,7 ]decane-2-ol acetate, and mixtures thereof; and a processing aid; wherein the weight ratio of the first fragrance material to the second fragrance material, if present, is from 100:0 to 1 :99.

[0075] The weight ratio of the first fragrance material (adamantyl ester containing compound) to the second fragrance material selected from the group of OTNE, 4-methyl-8-methylene-tricyclo[3.3.1.13 3,7 ]decane-2-ol acetate, and mixtures thereof, can be from 100:0 to 1 :99, preferably from 100:0 to 25:75, preferably from 100:0 to 50:50, more preferably from 100:0 to 51 :49, more preferably from 100:0 to 75:25, more preferably from 100:0 to 90:10, more preferably from 100:0 to 95:5, more preferably from 100:0 to 99:1.

[0076] Preferably, only the materials disclosed in this invention are formulated, omitting other fragrance materials. For example, consumer products may be substantially free of second fragrance materials, such as OTNE and 4-methyl-8-methylene-tricyclo[3.3.1.1] . 3,7 [Decan-2-ol ester. In particular, consumer products may contain compounds containing adamantyl esters and are substantially free of OTNE.]

[0077] The first fragrance material may be present in the consumer product as a free oil, or it may be part of a fragrance delivery system. For example, an adamantyl ester-containing compound may be encapsulated or otherwise associated with the delivery particles (e.g., embedded within the delivery particles). For example, the adamantyl ester-containing compound may be in the core of a core-shell delivery particle. The adamantyl ester-containing compound may be covalently or ionicly bonded, preferably covalently bonded to a carrier material, thereby forming a pre-fragrance material that releases the adamantyl ester-containing compound when the bonds are broken, such as by exposure to water or light. Thus, the first fragrance material (e.g., an adamantyl ester-containing compound) may be part of a fragrance delivery system, wherein the fragrance delivery system is a delivery particle, a pre-fragrance material, or a combination thereof.

[0078] As described above, consumer products contain processing aids. Processing aid materials may provide beneficial effects in the intended end use of the composition, or they may be processing aids and / or stabilizing agents. The exact nature of the processing aid and its incorporation level will depend on the physical form of the composition and the nature of the operation in which it is used. Those skilled in the art will be able to select the appropriate materials and levels for a given product or application.

[0079] Suitable processing aids may include antioxidants, surfactants, conditioning agents, deposition aids, rheology modifiers or structural agents, bleaching systems, stabilizers, detergent builders, chelating agents, dye transfer inhibitors, dispersants, enzymes, enzyme stabilizers, catalytic metal complexes, polymer dispersants, clay and dirt removers / anti-redeposition agents, brighteners, defoamers, siloxanes, toners, cosmetic dyes, fragrance additives, fragrance delivery systems, structural elasticizers, carriers, water-soluble growth promoters, processing aids, anti-agglomeration agents, coatings, formaldehyde removers, pigments, and mixtures thereof.

[0080] Processing aids may include a carrier. Such carriers can be hydrophilic (e.g., water) or hydrophobic (e.g., oil). The adamantyl ester-containing compounds described in this invention are relatively hydrophobic and can be readily coupled to hydrophobic carriers. Carriers particularly useful in consumer products include, but are not limited to, isopropyl myristate (IPM), Neobee... ®caprylyl / capric triglyceride, dipropylene glycol, propylene glycol monomethyl ether (DPM), tripropylene glycol monomethyl ether (TPM), triethyl citrate (TEC), or mixtures thereof. Thus, the consumer product can comprise a carrier, wherein the carrier is preferably IPM, DPM, or mixtures thereof. Preferably, the carrier comprises isopropyl myristate.

[0081] Isopropyl myristate, and other hydrophobic carriers, can be particularly useful when the adamantane-based ester-containing compound is encapsulated in certain core-shell delivery particles, such as those having an acrylate-based or chitosan-based shell. The core of the delivery particle can comprise isopropyl myristate and the adamantane-based ester-containing compound.

[0082] Fragrance composition

[0083] The present disclosure also relates to fragrance compositions. Such compositions generally comprise a mixture of fragrance ingredients. The fragrance compositions of the present disclosure can take the form of a premix or intermediate composition that is combined with other materials to make a final product, such as a consumer product.

[0084] For example, the fragrance composition can take the form of a fragrance composition that is a mixture of fragrance materials, such as a perfume accord that can be formulated into a consumer product.

[0085] The fragrance composition can comprise a first fragrance material and a second fragrance material that is different from the first fragrance material, wherein the first fragrance material is an adamantane-based ester-containing compound, preferably 2-adamantyl propionate, more preferably 2-adamantyl acetate, even more preferably 2-methyl-2-adamantyl acetate, and wherein the first fragrance material is present in an amount of at least 1% by weight of the fragrance composition.

[0086] The first fragrance material can be present in an amount of at least 0.005%, preferably at least 0.05%, or even 0.1%. The first fragrance material can be present in an amount of from about 0.005% to about 10%, preferably from about 0.05% to about 3%, more preferably from about 0.1% to about 1.5%. The first fragrance material can be present in an amount of at least 1%, preferably at least 2%, more preferably at least 5%, or even at least 10%, or even at least 20% by weight of the fragrance composition. The first fragrance material can be present in an amount of from 1% to about 99%, preferably from 1% to about 50%, more preferably from about 1% to about 25%, more preferably from about 1% to about 10%, even more preferably from about 1% to about 5% by weight of the fragrance composition.

[0087] The second fragrance material can be freely selected from any group of fragrance materials suitable for the intended product or end use. As used herein, the term "fragrance ingredient" (or "PRM") refers to a compound having a molecular weight of at least about 100 g / mol and which can be used alone or together with other fragrance ingredients to impart odor, aroma, flavor, or fragrance. Typical PRMs particularly include aromatic and / or aliphatic alcohols, ketones, aldehydes, esters, ethers, carboxylic acids, nitriles, nitrites, and alkenes, such as terpenes and alkynes. A list of common PRMs can be found in various references, such as "Perfume and Flavor Chemicals," Volumes I and II; Steffen Arctander Allured Pub. Co. (1994) and "Perfumes: Art, Science and Technology," Miller, PM and Lamparsky, D., Blackie Academic and Professional (1994).

[0088] As a non-limiting illustrative example, suitable second fragrance materials are provided in Table A below. The second fragrance material may be selected from the group or combination thereof provided in Table A.

[0089] Table A .

[0090]

[0091] In some embodiments, the second fragrance material may be OTNE or 4-methyl-8-methylene-tricyclo[3.3.1.1] 3,7 [Decan-2-ol ester]. That is, it may be particularly preferred to control the weight ratio of the adamantyl ester-containing compound to its counterpart. For example, the weight ratio of the adamantyl ester-containing compound to the second fragrance material may be 100:0 to 1:99, preferably 100:0 to 25:75, preferably 100:0 to 50:50, more preferably 100:0 to 51:49, more preferably 100:0 to 75:25, more preferably 100:0 to 90:10, more preferably 100:0 to 95:5, and more preferably 100:0 to 99:1.

[0092] To provide a complete and desired olfactory experience, the fragrance composition may contain three or more fragrance materials. The fragrance composition may also contain a third fragrance material. The fragrance composition may contain two to fifty fragrance materials, preferably two to thirty. For simplicity and ease of manufacture, it may be desirable to limit the number of components in the fragrance composition. For example, the fragrance composition may contain two to twenty, or to fifteen, or to ten fragrance materials.

[0093] The fragrance composition may also include a carrier, preferably isopropyl myristate (IPM) or Neobee. ® The carriers of caprylic / capric triglycerides, dipropylene glycol, propylene glycol monomethyl ether (DPM), tripropylene glycol monomethyl ester (TPM), triethyl citrate (TEC), or mixtures thereof, more preferably the carriers comprising isopropyl myristate.

[0094] Other useful carriers can be solvents or emulsifiers, such as nonionic surfactants, which can help incorporate the fragrance composition into the final product form. The fragrance composition can be in the form of an emulsion, preferably an oil-in-water emulsion.

[0095] The fragrance compositions disclosed herein can be incorporated into consumer products, as described in more detail above. Therefore, this disclosure relates to consumer products comprising fragrance compositions as described herein. Preferably, the consumer products are baby care products, beauty care products, fabric care products, home care products, household care products, feminine care products, health care products, food products, beverage products, high-quality fragrance products, or combinations thereof.

[0096] The fragrance composition may be present in the consumer product in an amount of at least 0.1%, preferably at least 0.5%, more preferably at least 1% by weight of the consumer product. The fragrance composition may be present in the consumer product in an amount of about 0.1% to about 99.9%, or about 0.1% to about 50%, or about 0.1% to about 25%, or about 0.1% to about 10%, or about 0.1% to about 5%, or about 1% to about 5% by weight of the consumer product.

[0097] Additional fragrance materials :

[0098] The fragrance compositions disclosed herein may also include additional fragrance materials. Some non-limiting examples of such fragrance materials are listed in Table B below. At least one of the additional fragrance materials listed in Table B may be used alone in a consumer product or in combination with any other fragrance materials disclosed herein in a consumer product.

[0099] Table B :

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] Method of making a consumer product

[0111] The present disclosure also relates to methods of making a consumer product. For example, the method can include the step of combining a first fragrance material with a treatment aid or a substrate, wherein the first fragrance material is a adamantyl ester-containing compound, preferably 2-adamantyl propionate, more preferably 2-adamantyl acetate, and even more preferably 2-methyl-2-adamantyl acetate.

[0112] Preferably, the first fragrance material is in liquid form. The first fragrance material can be combined with one or more other materials. For example, the first fragrance material can be part of a fragrance composition that includes at least a second fragrance material.

[0113] The first fragrance material can be part of a fragrance composition that can be combined with a treatment aid to form a consumer product.

[0114] The consumer product of the present disclosure can be formulated into any suitable form and made by any method selected by the formulator. The first fragrance material, the second fragrance material (if any), the fragrance composition, the treatment aid, and / or the base composition can be combined in a batch process, in a circulation loop process, and / or by an in-line mixing process. Suitable equipment for use in the processes disclosed herein can include continuous stirred tank reactors, homogenizers, turbo mixers, recirculation pumps, paddle mixers, high shear mixers, static mixers, plow shear mixers, ribbon blenders, vertical axis granulators, and tumble mixers (both in batch and continuous process configurations when available), spray dryers, and extruders.

[0115] The resulting composition can be placed in a container to form a consumer product as described herein. The container can be a bottle, preferably a plastic bottle, more preferably a plastic bottle comprising recycled plastic. The resulting composition can be placed in an aerosol or other spray container according to known methods.

[0116] The method can include the step of combining the first fragrance material with a substrate. The substrate can be a nonwoven sheet. The substrate can be an absorbent material or article. The first fragrance can be combined with the substrate by any suitable method, including spraying.

[0117] Treatment method

[0118] The present disclosure also relates to a method of treating a surface or environment with a diamond group-containing compound, preferably 2-methyl-2-diamantyl acrylate, more preferably 2-diamantyl propionate, more preferably 2-diamantyl acetate, and even more preferably 2-methyl-2-diamantyl acetate, as described in more detail above. The diamond group-containing compound can be part of a consumer product.

[0119] The method of treatment includes the step of providing the diamond group-containing compound to the surface or environment. Suitable surfaces can include fabric, hard surfaces, dishware, hair, or skin. Suitable environments can include interior spaces, such as rooms in a residential, commercial, or industrial environment.

[0120] The method can include the step of contacting a surface, preferably fabric, with the diamond group-containing compound, optionally as part of a consumer product according to the present disclosure.

[0121] The method can include the step of providing the diamond group-containing compound, optionally as part of a consumer product according to the present disclosure, to an environment, preferably an interior environment. The step of providing the diamond group-containing compound can be by a spraying method or by diffusion.

[0122] Use

[0123] The present disclosure also relates to the use of a diamond group-containing compound, preferably 2-diamantyl propionate, more preferably 2-diamantyl acetate, and even more preferably 2-methyl-2-diamantyl acetate, to provide a pleasing fragrance to a consumer product, surface, or environment. Such materials, products, surfaces, and environments are discussed in more detail above.

[0124] Combination

[0125] Specific contemplated combinations of the present disclosure are described herein in the following paragraphs labeled alphabetically. These combinations are exemplary in nature, and are not limiting.

[0126] A. A consumer product comprising: a first fragrance material consisting of the compound G-C(O)-O-Q; wherein G and Q are carbon-containing groups connected only through an ester linkage; wherein Q comprises a single adamantyl moiety; wherein only one carbon atom of the adamantyl moiety is substituted with something other than -H; wherein the compound is selected from the group consisting of:

[0127] i) (Formula 1); or

[0128] ii) (Formula 2); or

[0129] iii) mixtures thereof;

[0130] wherein for Formula 1 or Formula 2:

[0131] a. R is hydrogen or a hydrocarbyl group;

[0132] b. E contains only a single -CO2- moiety;

[0133] c. the molecular formula is C 11+n H 16+2n-m O2,

[0134] wherein n is an integer from 1 to 7, and m is 0 or 2; and

[0135] wherein when m is 0, the molecule contains no carbon-carbon double bonds; and

[0136] wherein when m is 2, the molecule contains a single carbon-carbon double bond; and

[0137] b) a treatment adjunct; and wherein the first fragrance material is present in an amount of at least 0.0005% by weight of the consumer product composition.

[0138] B. The consumer product according to paragraph A, wherein n is an integer from 1 to 5.

[0139] C. The consumer product according to either paragraph A or B, wherein n is an integer from 1 to 3.

[0140] D. The consumer product according to any of paragraphs A to C, wherein n is an integer from 1 to 2.

[0141] E. The consumer product according to any of paragraphs A to D, wherein m is 0.

[0142] F. The consumer product according to any of paragraphs A to E, wherein the first fragrance material is selected from the group consisting of:

[0143] a) and

[0144] b) and

[0145] c) and

[0146] d) and

[0147] e) and

[0148] f) and

[0149] g) mixtures thereof.

[0150] G. The consumer product according to any of paragraphs A to F, further comprising a second fragrance material selected from the group consisting of:

[0151] a)

[0152] b) and

[0153] c) mixtures thereof.

[0154] H. The consumer product according to any of paragraphs A to G, wherein the consumer product further comprises an antioxidant and the first fragrance material is:

[0155] .

[0156] I. The consumer product according to any of paragraphs A to H, wherein the consumer product further comprises an antioxidant and the first fragrance material is:

[0157] .

[0158] J. The consumer product according to any of paragraphs A to I, wherein the weight ratio of the first fragrance material to the second fragrance material is from 100:0 to 25:75, preferably from 100:0 to 50:50, more preferably from 100:0 to 51 :49, more preferably from 100:0 to 75:25, more preferably from 100:0 to 90:10, more preferably from 100:0 to 95:5, more preferably from 100:0 to 99:1.

[0159] K. The consumer product according to any of paragraphs A to J, wherein the first fragrance material is present in the consumer product in an amount of at least 0.001%, preferably at least 0.01%, more preferably at least 0.1%, more preferably at least 0.5%, more preferably at least 1%, by weight of the consumer product.

[0160] L. The consumer product according to any of paragraphs A to K, wherein the first fragrance material is present in the consumer product in an amount of at least 0.001%, preferably at least 0.01%, more preferably at least 0.1%, more preferably at least 0.5%, more preferably at least 1%, by weight of the consumer product.

[0161] M. The consumer product according to any of paragraphs A to L, wherein the first fragrance material is part of a perfume delivery system, wherein the perfume delivery system is a delivery particle, a pro-fragrance material, or a combination thereof.

[0162] N. The consumer product according to any of paragraphs A to M, wherein the first fragrance material is part of a perfume delivery system, wherein the perfume delivery system is a delivery particle, a pro-fragrance material, or a combination thereof.

[0163] O. The consumer product according to any of paragraphs A to N, wherein the treatment adjunct is selected from the group consisting of surfactants, conditioning actives, deposition aids, rheology modifiers, structurants, bleach systems, stabilizers, builders, chelants, dye transfer inhibitors, dispersants, enzymes, enzyme stabilizers, catalytic metal complexes, polymeric dispersants, clays and soil removal / anti-redeposition agents, whitening agents, suds suppressors, silicones, hueing agents, aesthetic dyes, neat fragrance, additional perfume delivery systems, structure elasticizing agents, carriers, hydrotropes, processing aids, anti-agglomeration agents, coatings, formaldehyde scavengers, pigments, or mixtures thereof.

[0164] P. The consumer product according to any of paragraphs A to O, wherein the treatment adjunct comprises a carrier, preferably a carrier comprising isopropyl myristate (IPM), Neobee ® caprylyl / capryl triglyceride, dipropylene glycol, propylene glycol monomethyl ether (DPM), tripropylene glycol monomethyl ether (TPM), triethyl citrate (TEC), or mixtures thereof, more preferably a carrier comprising isopropyl myristate.

[0165] Q. The consumer product according to any of paragraphs A to P, wherein the consumer product is a baby care product, a beauty care product, a fabric care product, a home care product, a household care product, a feminine care product, a health care product, a food product, a beverage product, a premium fragrance product, or a combination thereof.

[0166] R. The consumer product according to any of paragraphs A to Q, wherein the consumer product is a fabric care product and / or a home care product, wherein the home care product is selected from the group consisting of a hard surface cleaner, a dish care product, an air care product, or a combination thereof.

[0167] S. The consumer product according to any of paragraphs A to R, wherein the consumer product comprises a form selected from the group consisting of: a liquid composition, a particulate composition, a hydrocolloid, a single-compartment pouch, a multi-compartment pouch, a dissolvable sheet, a pastille or bead, a fibrous article, a tablet, a stick, a bar, a flake, a spray, a foam / mousse, a nonwoven sheet, a cream, an absorbent article, a paste, a gel, an adhesive, an adhesive patch, or a mixture thereof.

[0168] T. A method of making a consumer product, the method comprising the steps of:

[0169] combining a first fragrance material with a processing aid or a substrate, wherein the first fragrance material is a compound G-C(O)-O-Q; wherein G and Q are carbon-containing groups connected only through an ester linkage; wherein Q comprises a single adamantyl moiety; wherein only one carbon atom of the adamantyl moiety is substituted with something other than -H; wherein the compound is selected from the group consisting of:

[0170] i) (Form 1); or

[0171] ii) (Form 2); or

[0172] iii) a mixture thereof;

[0173] wherein for Form 1 or Form 2:

[0174] A) R is hydrogen or a hydrocarbyl group;

[0175] B) E contains only a single -CO2- moiety;

[0176] C) the molecular formula is C 11+n H 16+2n-m O2,

[0177] wherein n is an integer from 1 to 7, and m is 0 or 2; and

[0178] wherein when m is 0, the molecule contains no carbon-carbon double bonds; and

[0179] wherein when m is 2, the molecule contains a single carbon-carbon double bond.

[0180] U. The method according to paragraph T, wherein the first fragrance material is in liquid form.

[0181] V. A method of treating a surface or environment, the method comprising the step of providing to the surface or environment a compound G-C(O)-O-Q, wherein G and Q are carbon-containing groups connected only through an ester linkage; wherein Q comprises a single adamantyl moiety; wherein only one carbon atom of the adamantyl moiety is substituted with something other than -H; wherein the compound is selected from the group consisting of:

[0182] i) (Formula 1); or

[0183] ii) (Formula 2); or

[0184] iii) mixtures thereof;

[0185] wherein for Formula 1 or Formula 2:

[0186] A) R is hydrogen or a hydrocarbyl group;

[0187] B) E contains only a single -CO2- moiety;

[0188] C) the molecular formula is C 11+n H 16+2n-m O2,

[0189] wherein n is an integer from 1 to 7, and m is 0 or 2; and

[0190] wherein when m is 0, the molecule contains no carbon-carbon double bonds; and

[0191] wherein when m is 2, the molecule contains a single carbon-carbon double bond.

[0192] W. Use of a compound G-C(O)-O-Q to provide a fragrance to a consumer product, surface, or environment, wherein G and Q are carbon-containing groups connected only through an ester linkage; wherein Q comprises a single adamantyl moiety; wherein only one carbon atom of the adamantyl moiety is substituted with something other than -H; wherein the compound is selected from the group consisting of:

[0193] i) (Formula 1); or

[0194] ii) (Formula 2); or

[0195] iii) mixtures thereof;

[0196] wherein for Formula 1 or Formula 2:

[0197] A) R is hydrogen or a hydrocarbyl group;

[0198] B) E contains only a single -CO2- moiety;

[0199] C) the molecular formula is C11+n H 16+2n-m O2,

[0200] wherein n is an integer from 1 to 7, and m is 0 or 2; and

[0201] wherein when m is 0, the molecule does not contain a carbon-carbon double bond; and

[0202] wherein when m is 2, the molecule contains a single carbon-carbon double bond.

[0203] Test method

[0204] It is understood that the test methods disclosed in the Test Methods section of the present application should be used to determine the respective parameter values for the subject matter for which the Applicant claims protection as claimed and described herein.

[0205] Headspace method

[0206] Perfume headspace data was collected for various materials according to the methods provided below.

[0207] Partition coefficients were calculated by determining the amount of PRM in the headspace above a solution with a known concentration using GC / FID-MS (Agilent 7890 and 5977A MSD) with a thermal desorption unit (Gerstel MPS2) and a dynamic headspace sampler (Gerstel DHS). This technique allows for automated headspace collection using a MultiPurpose Sampler (MPS). The PRM of interest was prepared in isopropyl myristate (IPM) or propylene glycol monomethyl ether (DPM) at a known concentration and 1 mL was pipetted into a 20 mL headspace vial.

[0208] DHS conditions: The sample was tempered in this unit at 30 °C. A helium flow of 10 ml / min swept the 20 mL headspace above the sample containing the analyte onto a sorbent tube (TDU) containing 25 mg Tenax TA 35 / 60 (Restek Cat. No. 25701).

[0209] TDU conditions: The sorbent tube was desorbed with a program starting with 2 minutes of solvent purge at 30 °C, then ramping to 270 °C at 720 °C / min and holding for 8 minutes. The analyte was refocused on a glass bead frit at -60 °C, then desorbed at a rate of 12 °C / s to 270 °C onto the GC column.

[0210] GC / MS conditions: An Agilent 122-5532UI column of 30 m x 250 pm x 0.25 pm was used with a flow rate of 1.5 mL / min. A temperature program of 50 °C to 280 °C, hold for 2 min, and a ramp rate of 12 °C / min was appropriate. Scan or SIM MSD parameters with solvent delay of DPM were applied to achieve proper detection.

[0211] Analytical standards were available from AK Scientific, Inc., Union City, CA 94587, USA. Stock solutions were prepared at approximately 0.5 g / L. The stock solutions were then diluted to 4 to 5 concentrations ranging from approximately 0.05 g / L to 0.00005 g / L. These standard solutions were then analyzed by GC / MS. This analysis was performed by using the same TDU desorption and GC / MS conditions described above, with 1 uL of liquid injected onto the TDU tube instead of DHS collection. The area response of the injection amount on the column and the target m / z was used to create a calibration curve with a linear fit.

[0212] The quantification of the headspace was performed by the PRM target m / z area response of the fragrance components and the linear equation of the calibration curve.

[0213] Examples

[0214] The examples provided below are intended to be illustrative in nature and are not intended to be limiting.

[0215] Example 1. Headspace data

[0216] Fragrance headspace data was collected for various materials according to the headspace method provided above in the test method section. Air / solvent partition coefficients were determined and indexed accordingly (e.g., where the partition coefficient of OTNE was set to 1.00).

[0217] Results for 2-adamantyl propionate, 2-adamantyl acetate, and 2-methyl-2- adamantyl acetate in isopropyl myristate (IPM) are provided in Table 1 below.

[0218] Table 1

[0219]

[0220]

[0221] In summary, the adamantyl ester-containing compounds tested were found in headspace about 5.5 to 8.7 times more than OTNE in IPM, a common solvent used in perfume delivery particles. The increased volatility of the adamantyl ester-containing compounds compared to OTNE is advantageous because a higher fraction of the adamantyl ester-containing compounds would be found in air from a consumer product. Thus, the adamantyl ester-containing compounds would be more likely to be perceived at lower levels in a consumer product, or at the same level more intensely perceived in a consumer product.

[0222] The dimensions and values disclosed herein are not to be understood as being strictly limited to the exact numerical values recited. Instead, unless otherwise specified, each such dimension is intended to mean both the exact value and a functional equivalent range surrounding that value. For example, a dimension disclosed as "40 mm" is intended to mean "about 40 mm."

[0223] Every document cited herein, including any cross referenced or related patent or application and any patent application or patent to which this application claims priority or benefit thereof, is hereby incorporated herein by reference in its entirety unless expressly excluded or otherwise limited. The citation of any document is not an admission that it is prior art with respect to any application disclosed or claimed herein or that it alone, or along with any other document or together with any relevant art, teaches, suggests or discloses any such application. Further, to the extent that any meaning or definition of a term in this document conflicts with any meaning or definition of the same term in a document incorporated by reference, the meaning or definition assigned to that term in this document shall control. In addition, the bulletin of the United States Patent and Trademark Office, "Changes To Implement the AIA Patent Law," 77 Federal Register 20999, 21000 (April 6, 2012) is hereby incorporated by reference into this document.

[0224] While particular embodiments of the present application have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the application. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this application.

Claims

1. A consumer product comprising: a) a first fragrance material consisting of the compound G-C(O)-O-Q; wherein G and Q are carbon-containing groups connected only through an ester linkage; wherein Q comprises a single adamantyl moiety; wherein only one carbon atom of the adamantyl moiety is substituted with something other than -H; wherein the compound is selected from the group consisting of: i) (Formula 1); or ii) (Formula 2); or iii) mixtures thereof; wherein for Formula 1 or Formula 2: a. R is hydrogen or a hydrocarbyl group; b. E contains only a single -CO2- moiety; c. Formula C 11+n H 16+2n-m O2, wherein n is an integer from 1 to 7, and m is 0 or 2; and wherein when m is 0, the molecule contains no carbon-carbon double bonds; and wherein when m is 2, the molecule contains a single carbon-carbon double bond; and b) a processing aid; and wherein the first fragrance material is present in an amount of at least 0.0005% by weight of the consumer product composition.

2. The consumer product of claim 1, wherein n is an integer from 1 to 5.

3. The consumer product of any preceding claim, wherein n is an integer from 1 to 3.

4. The consumer product of any preceding claim, wherein n is an integer from 1 to 2.

5. The consumer product of any preceding claim, wherein m is 0.

6. The consumer product of any preceding claim, wherein the first fragrance material is selected from the group consisting of: a) and b) and c) and d) and e) and f) and g) mixtures thereof.

7. The consumer product of any preceding claim, further comprising a second fragrance material selected from the group consisting of: a) b) and c) mixtures thereof.

8. The consumer product of any preceding claim, wherein the consumer product further comprises an antioxidant, and the first fragrance material is: 。 9. The consumer product of any preceding claim, wherein the consumer product further comprises an antioxidant, and the first fragrance material is: 。 10. The consumer product of any preceding claim, wherein the weight ratio of the first fragrance material to the second fragrance material is 100:0 to 25:75, preferably 100:0 to 50:50, more preferably 100:0 to 51:49, more preferably 100:0 to 75:25, more preferably 100:0 to 90:10, more preferably 100:0 to 95:5, more preferably 100:0 to 99:

1.

11. The consumer product of any preceding claim, wherein the first fragrance material is present in the consumer product in an amount of at least 0.001%, preferably at least 0.01%, more preferably at least 0.1%, more preferably at least 0.5%, more preferably at least 1%, by weight of the consumer product.

12. The consumer product of any preceding claim, wherein the first fragrance material is present in the consumer product in an amount of at least 0.001%, preferably at least 0.01%, more preferably at least 0.1%, more preferably at least 0.5%, more preferably at least 1%, by weight of the consumer product.

13. The consumer product of any preceding claim, wherein the first fragrance material is part of a perfume delivery system, wherein the perfume delivery system is a delivery particle, a pro-fragrance material, or a combination thereof.

14. The consumer product of any preceding claim, wherein the first fragrance material is part of a perfume delivery system, wherein the perfume delivery system is a delivery particle, a pro-fragrance material, or a combination thereof.

15. The consumer product of any preceding claim, wherein the treatment adjunct is selected from the group consisting of surfactants, conditioning actives, deposition aids, rheology modifiers, structurants, bleach systems, stabilizers, builders, chelating agents, dye transfer inhibitors, dispersants, enzymes, enzyme stabilizers, catalytic metal complexes, polymeric dispersing agents, clays and soil removal / anti-redeposition agents, whitening agents, suds suppressors, silicones, hueing agents, aesthetic dyes, neat perfumes, additional perfume delivery systems, structure elasticizing agents, carriers, hydrotropes, processing aids, anti-agglomeration agents, coatings, formaldehyde scavengers, pigments, or mixtures thereof.

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