Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
  • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
  • C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
  • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0069—Heterocyclic compounds
  • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
  • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0069—Heterocyclic compounds
  • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
  • C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms

Definitions

• the present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or perfume delivery systems, as well as processes for making and using such perfume raw materials, perfume delivery systems and consumer products.
• Consumer products may comprise one or more perfumes and/or perfume delivery systems that can mask an undesirable odor and/or provide a desired scent to a product and/or a situs that is contacted with such a product. While current perfumes and perfume delivery systems provide desirable fragrances, consumers continue to seek products that have scents that may be longer lasting and that are tailored to their individual desires (see for example USPA 2007/0275866 Al and USPA 2008/0305977 Al) - unfortunately the pool of perfume raw materials and perfume delivery systems that is available is still too limited to completely meet the perfume community's needs. Thus, perfumers need an ever larger pool of perfume raw materials and perfume delivery systems.
• perfume raw materials and perfumes including the delivery systems, disclosed herein expand the perfume community's options, as such perfume raw materials can provide variations on character and such perfumes can provide desired odor profiles in consumer products.
• such perfume delivery systems comprising such perfume raw materials may provide variations on character and/or odor profiles that are better than expected as measured by parameters such as headspace analysis (employed to determine perfume delivery system perfume leakage and/or perfume delivery efficiency), ClogP, boiling point and/or odor detection threshold.
• the present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or such perfume delivery systems, as well as processes for making and using such perfume raw materials, perfume delivery systems and consumer products.
• consumer product means baby care, beauty care, fabric & home care, family care, feminine care, health care, snack and/or beverage products or devices generally intended to be used or consumed in the form in which it is sold.
• Such products include but are not limited to diapers, bibs, wipes; products for and/or methods relating to treating hair (human, dog, and/or cat), including, bleaching, coloring, dyeing, conditioning, shampooing, styling; deodorants and antiperspirants; personal cleansing; cosmetics; skin care including application of creams, lotions, and other topically applied products for consumer use including fine fragrances; and shaving products, products for and/or methods relating to treating 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
• cleaning and/or treatment composition is a subset of consumer products that includes, unless otherwise indicated, beauty care, fabric & home care products.
• Such products include, but are not limited to, products for treating hair (human, dog, and/or cat), including, bleaching, coloring, dyeing, conditioning, shampooing, styling; deodorants and antiperspirants; personal cleansing; cosmetics; skin care including application of creams, lotions, and other topically applied products for consumer use including fine fragrances; and shaving products, products for treating 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, granular or powder-form all-purpose or "heavy-duty" washing agents, especially cleaning detergents; liquid, gel or paste-form all-purpose washing agents, especially the so-called heavy-duty liquid types; liquid fine-fabric detergents; hand dishwashing agents or light duty dishwashing agents, especially those of the high-foaming type; machine dish
• the term "fabric and/or hard surface cleaning and/or treatment composition” is a subset of cleaning and treatment compositions that includes, unless otherwise indicated, granular or powder-form all-purpose or "heavy-duty” washing agents, especially cleaning detergents; liquid, gel or paste-form all-purpose washing agents, especially the so-called heavy-duty liquid types; liquid fine-fabric detergents; hand dishwashing agents or light duty dishwashing agents, especially those of the high-foaming type; machine dishwashing agents, including the various tablet, granular, liquid and rinse-aid types for household and institutional use; liquid cleaning and disinfecting agents, including antibacterial hand-wash types, cleaning bars, car or carpet shampoos, bathroom cleaners including toilet bowl cleaners; and metal cleaners, fabric conditioning products including softening and/or freshening that may be in liquid, solid and/or dryer sheet form ; as well as cleaning auxiliaries such as bleach additives and "stain-stick" or pre-treat types, substrate-laden products such as dryer added sheets, dry and we
• solid includes granular, powder, bar and tablet product forms.
• fluid includes liquid, gel, paste and gas product forms.
• suid includes paper products, fabrics, garments, hard surfaces, hair and skin.
• perfume raw materials include molecules that can serve the purposes of providing odour and/or a sensation such as cooling.
• component or composition levels are in reference to the active portion of that component or composition, and are exclusive of impurities, for example, residual solvents or by-products, which may be present in commercially available sources of such components or compositions.
• Suitable molecules include the PRMs listed in Table 1 below and stereoisomers thereof.
• the PRMs disclosed in Table 1 above may provide one or more of the following benefits at levels that Applicants believe are unexpected in view of PRMs in general: neat product odor; wet fabric odor when applied to a fabric; dry fabric odor when applied to a fabric; reduced leakage from an encapsulate, including an encapsulate such as a perfume microcapsule; increased head space versus neat oil in certain perfume delivery technologies; odor when used in a matrix perfume delivery that is applied to a package; neat product odor when applied to a cleaning and/or treatment composition; fine fragrance composition odor when used in a fine fragrance; dry hair odor when a composition comprising such a PRM is applied to hair; PRM bloom from a solution comprising such a PRM; and new PRM character when applied to a situs.
• PRMs and stereoisomers of such PRMs disclosed in Table 1 above can be made in accordance with the teachings detailed in the present specification. Moreover, these PRMs are liquid at room temperature. As a result, their t application in perfumes and products is facilitated..
• the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use, as defined by the present specification, in consumer products at levels, based on total consumer product weight, of from about 0.0001 % to about 25%, from about 0.0005% to about 10%, from about 0.001% to about 5%, from about 0.005% to about 2.5%, or even from 0.01% to about 1%.
• Such PRMs and stereoisomers thereof may be used in various combinations in the aforementioned consumer products.
• a consumer product may comprise one or more PRMs selected from Table 1 PRMs Nos. 1 and 2 and stereoisomers thereof.
• the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use, as defined by the present specification, in cleaning and/or treatment compositions at levels, based on total cleaning and treatment products weight of from about 0.0001 % to about 25%, from about 0.0005% to about 10%, from about 0.001% to about 5%, from about 0.005% to about 2.5%, or even from 0.01 % to about 1%.
• Such PRMs and stereoisomers thereof may be used in various combinations in the aforementioned cleaning and/ treatment compositions.
• a cleaning and/or treatment composition may comprise one or more PRMs selected from Table 1 PRMs Nos. 1 and 2 and stereoisomers thereof.
• the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use, as defined by the present specification, in fabric and/or hard surface cleaning and/or treatment compositions at levels, based on total fabric and/or hard surface cleaning and/or treatment composition weight of from about 0.00001% to about 25%, from 0.00005% to about 10%, from 0.0001% to about 5%, from 0.0005% to about 1.0%, or even from 0.001% to about
• a fabric and/or hard surface cleaning and/or treatment composition may comprise one or more PRMs selected from Table 1 PRMs Nos. 1 and 2 and stereoisomers thereof.
• a detergent that may comprise the same level of the PRMs as disclosed for the aforementioned fabric and hard surface cleaning and/or treatment compositions is disclosed.
• a detergent may comprise one or more PRMs selected from Table 1 PRMs Nos. 1 and 2 and stereoisomers thereof.
• the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in highly compacted consumer products, including highly compacted fabric and hard surface cleaning and/or treatment compositions.
• the PRMs disclosed in Table 1 and stereoisomers thereof may be employed in solid or fluid highly compacted detergents at levels of from about 0.00001% to about 25%, from 0.00005% to about 10%, from 0.0001% to about 5%, from 0.0005% to about 1.0%, or even from 0.001% to about 0.5%, based on total composition weight.
• Such PRMs and stereoisomers thereof may be used in various combinations in the aforementioned highly compacted detergent compositions.
• Such highly compact detergents typically comprise a higher than normal percentage of active ingredients.
• a highly compacted detergent may comprise one or more PRMs selected from Table 1 PRMs Nos. 1 and 2 and stereoisomers thereof.
• perfume delivery systems Certain perfume delivery systems, methods of making certain perfume delivery systems and the uses of such perfume delivery systems are disclosed in USPA 2007/0275866 Al. Such perfume delivery systems include:
• PAD Polymer Assisted Delivery
• This perfume delivery technology uses polymeric materials to deliver perfume materials.
• PAD include employment of classical coacervation, water soluble or partly soluble to insoluble charged or neutral polymers, liquid crystals, hot melts, hydrogels, perfumed plastics, microcapsules, nano- and micro-latexes, polymeric film formers, and polymeric absorbents, etc. Further, PAD includes, but is not limited to:
• Perfume materials may be 1) dispersed into the polymer prior to formulating into the product or 2) added separately from the polymer during or after formulation of the product.
• Suitable organic latex particles include a wide range of materials including, but not limited to, polyacetal, polyacrylate, polyamide, polybutadiene, polychloroprene, polyethylene, polycyclohexylene polycarbonate, polyhydroxyalkanoate, polyketone, polyester, polyetherimide, polyethersulfone, polyethylenechlorinates, polyimide, polyisoprene, polylactic acid, polypheny lene, polyphenylene, polypropylene, polystyrene, polysulfone, polyvinyl acetate, polyvinyl chloride, as well as polymers or copolymers based on amine, acrylonitrile-butadiene, cellulose acetate, ethylene- vinyl acetate, ethylene vinyl alcohol, styrene -butadiene, vinyl acetate- ethylene, and mixtures thereof.
• All such matrix systems may include, for example, polysaccharides and nanolatexes that may be combined with other perfume delivery technologies, including other PAD systems such as PAD reservoir systems in the form of a perfume microcapsule (PMC).
• PMC perfume microcapsule
• Silicone-assisted delivery (SAD) may also be used. Examples of silicones include polydimethylsiloxane and poly alky Idimethylsiloxanes. Other examples include those with amine functionality, which may be used to provide benefits associated with amine- assisted delivery (AAD) and/or polymer-assisted delivery (PAD) and/or amine-reaction products (ARP).
• AAD amine- assisted delivery
• PAD polymer-assisted delivery
• ARP amine-reaction products
• Reservoir systems are also known as core-shell systems (e.g. , perfume microcapsules).
• the benefit agent is surrounded by a benefit agent release controlling membrane, which may serve as a protective shell.
• Suitable shell materials include reaction products of one or more amines with one or more aldehydes, such as urea cross- linked with formaldehyde or gluteraldehyde, melamine cross-linked with formaldehyde, gelatin- polyphosphate coacervates optionally cross-linked with gluteraldehyde, gelatin-gum arabic coacervates, cross-linked silicone fluids, polyamine reacted with polyisocyanates, polyamines reacted with epoxides, polyvinyl alcohol cross linked with gluteraldehyde, polydivinyl chloride, polyesters, polyamides, polyacrylates and mixtures thereof.
• aldehydes such as urea cross- linked with formaldehyde or gluteraldehyde, melamine cross-linked with formaldehyde, gelatin- polyphosphate coacervates optionally cross-linked with gluteraldehyde, gelatin-gum arabic coacervates, cross-linked
• said polyacrylate based materials may comprise polyacrylate formed from methylmethacrylate/ dimethylaminomethyl methacrylate, polyacrylate formed from amine acrylate and/or methacrylate and strong acid, polyacrylate formed from carboxylic acid acrylate and/or methacrylate monomer and strong base, polyacrylate formed from an amine acrylate and/or methacrylate monomer and a carboxylic acid acrylate and/or carboxylic acid methacrylate monomer, and mixtures thereof.
• Suitable core materials include perfume compositions, perfume raw materials, silicone oils, waxes, hydrocarbons, higher fatty acids, essential oils, lipids, skin coolants, vitamins, sunscreens, antioxidants, glycerine, catalysts, bleach particles, silicon dioxide particles, malodor reducing agents, odor-controlling materials, chelating agents, antistatic agents, softening agents, insect and moth repelling agents, colorants, antioxidants, chelants, bodying agents, drape and form control agents, smoothness agents, wrinkle control agents, sanitization agents, disinfecting agents, germ control agents, mold control agents, mildew control agents, antiviral agents, drying agents, stain resistance agents, soil release agents, fabric refreshing agents and freshness extending agents, chlorine bleach odor control agents, dye fixatives, dye transfer inhibitors, color maintenance agents, optical brighteners, color restoration/rejuvenation agents, anti-fading agents, whiteness enhancers, anti-abrasion agents, wear resistance agents, fabric integrity agents, anti- wear agents, anti-pilling agents, def
• Suitable perfume compositions may comprise enduring perfumes, such as perfume raw materials that have a cLogP greater than about 2.5 and a boiling point greater than about 250°C. Further, suitable perfume compositions may comprise blooming perfumes that comprise perfume raw materials that have a cLogP of greater than about 3 and a boiling point of less than about 260°C.
• Suitable core materials can be stabilized and/or emulsified in solvent systems with organic or inorganic materials (organic materials can be polymers of anionic nature, non-ionic nature or cationic nature, like polyacrylates and polyvinyl alcohol).
• Suitable processes to make core-shell systems include coating, extrusion, spray drying, interfacial polymerization, polycondensation, simple coacervation, complex coacervation, free radical polymerization, in situ emulsion polymerization, matrix polymerization and combinations thereof.
• Suitable characteristics for the core-shell systems include: a) a shell thickness of from about 20 nm to about 500 nm, from about 40 nm to about 250 nm, or from about 60 nm to about 150 nm;
• a shell core ratio of from about 5:95 to about 50:50, from about 10:90 to about 30:70, or from about 10:90 to about 15:85;
• a fracture strength of from about 0.1 MPa to about 16 MPa, from about 0.5 MPa to about 8 MPa, or even from about 1 MPa to about 3 MPa; and d) an average particle size of from about 1 micron to about 100 microns, from about 5 microns to about 80 microns, or even from about 15 microns to about 50 microns.
• Suitable deposition and/or retention enhancing coatings that may be applied to the core- shell systems include non-ionic polymers, anionic polymers, cationic polymers such as polysaccharides including, but not limited to, cationically modified starch, cationically modified guar, polysiloxanes, poly diallyl dimethyl ammonium halides, copolymers of poly diallyl dimethyl ammonium chloride and vinyl pyrrolidone, acrylamides, imidazoles, imidazolinium halides, imidazolium halides, poly vinyl amine, copolymers of poly vinyl amine and N-vinyl formamide and mixtures thereof.
• non-ionic polymers such as polysaccharides including, but not limited to, cationically modified starch, cationically modified guar, polysiloxanes, poly diallyl dimethyl ammonium halides, copolymers of poly diallyl dimethyl ammonium chloride and vinyl pyrrolidone
• suitable coatings may be selected from the group consisting of polyvinylformaldehyde, partially hydroxylated polyvinylformaldehyde, polyvinylamine, polyethyleneimine, ethoxylated polyethyleneimine, polyvinylalcohol, polyacrylates and combinations thereof.
• Suitable methods of physically reducing and/or removing any residual type materials from the core-shell making process may be employed, such as centrifugation.
• Suitable methods of chemically reducing any residual type materials may also be employed, such as the employment of scavengers, for example formaldehyde scavengers including sodium bisulfite, urea, ethylene urea, cysteine, cysteamine, lysine, glycine, serine, carnosine, histidine, glutathione, 3,4-diaminobenzoic acid, allantoin, glycouril, anthranilic acid, methyl anthranilate, methyl 4- aminobenzoate, ethyl acetoacetate, acetoacetamide, malonamide, ascorbic acid, 1,3- dihydroxyacetone dimer, biuret, oxamide, benzoguanamine, pyroglutamic acid, pyrogallol, methyl gallate, ethyl gallate,
• Non-polymer materials or molecules may also serve to improve the delivery of perfume.
• perfume may non- covalently interact with organic materials, resulting in altered deposition and/or release.
• organic materials include but are not limited to hydrophobic materials such as organic oils, waxes, mineral oils, petrolatum, fatty acids or esters, sugars, surfactants, liposomes and even other perfume raw material (perfume oils), as well as natural oils, including body and/or other soils.
• situs itself may serve to improve the delivery of perfume.
• the situs itself may be a perfume delivery technology.
• different fabric types such as cotton or polyester will have different properties with respect to ability to attract and/or retain and/or release perfume.
• the amount of perfume deposited on or in fibers may be altered by the choice of fiber, and also by the history or treatment of the fiber, as well as by any fiber coatings or treatments. Fibers may be pre-loaded with a perfume, and then added to a product that may or may not contain free perfume and/or one or more perfume delivery technologies.
• Amine Assisted Delivery The amine-assisted delivery technology approach utilizes materials that contain an amine group to increase perfume deposition or modify perfume release during product use. There is no requirement in this approach to pre-complex or pre-react the perfume raw material(s) and the amine prior to addition to the product.
• amine - containing AAD materials suitable for use herein may be non-aromatic, for example,
• poly alky limine such as polyethyleneimine (PEI), or polyvinylamine (PVAm); or aromatic, for example, anthranilates.
• PEI polyethyleneimine
• PVAm polyvinylamine
• Such materials may also be polymeric or non-polymeric.
• such materials contain at least one primary amine.
• a material that contains a heteroatom other than nitrogen, for example sulfur, phosphorus or selenium, may be used as an alternative to amine compounds.
• the aforementioned alternative compounds can be used in combination with amine compounds.
• a single molecule may comprise an amine moiety and one or more of the alternative heteroatom moieties, for example, thiols, phosphines and selenols.
• Cyclodextrin Delivery System This technology approach uses a cyclic oligosaccharide or cyclodextrin to improve the delivery of perfume. Typically a perfume and cyclodextrin (CD) complex is formed. Such complexes may be preformed, formed in-situ, or formed on or in the situs.
• SEA's are starch encapsulated perfume materials. Suitable starches include modified starches such as hydrolyzed starch, acid thinned starch, starch having hydrophobic groups, such as starch esters of long chain hydrocarbons (C5 or greater), starch acetates, starch octenyl succinate and mixtures thereof. In one aspect, starch esters, such as starch octenyl succinates, are employed.
• Suitable perfumes for encapsulation include the HIA perfumes, including those having a boiling point determined at the normal standard pressure of about 760 mmHg of 275 °C or lower, an octanol/water partition coefficient P of about 2000 or higher and an odor detection threshold of less than or equal 50 parts per billion (ppb).
• the perfume may have logP of 2 or higher.
• ZIC Inorganic Carrier Delivery System
• PZ perfume-loaded zeolite
• Suitable zeolite and inorganic carriers as well as methods of making same may be found in USPA 2005/0003980 Al.
• Silica is another form of ZIC.
• Another example of a suitable inorganic carrier includes inorganic tubules, where the perfume or other active material is contained within the lumen of the nano- or micro-tubules.
• the perfume-loaded inorganic tubule is a mineral nano- or micro-tubule, such as halloysite or mixtures of halloysite with other inorganic materials, including other clays.
• the PLT technology may also comprise additional ingredients on the inside and/or outside of the tubule for the purpose of improving in-product diffusion stability, deposition on the desired situs or for controlling the release rate of the loaded perfume.
• Monomeric and/or polymeric materials, including starch encapsulation may be used to coat, plug, cap, or otherwise encapsulate the PLT. Suitable PLT systems as well as methods of making same may be found in USP 5,651,976. VIII.
• Pro-Perfume This technology refers to perfume technologies that result from the reaction of perfume materials with other substrates or chemicals to form materials that have a covalent bond between one or more PRMs and one or more carriers.
• the PRM is converted into a new material called a pro-PRM (i.e. , pro-perfume), which then may release the original PRM upon exposure to a trigger such as water or light.
• pro-perfumes include Michael adducts (e.g. , beta-amino ketones), aromatic or non-aromatic imines (Schiffs Bases), oxazolidines, beta-keto esters, and orthoesters.
• Another aspect includes compounds comprising one or more beta-oxy or beta-thio carbonyl moieties capable of releasing a PRM, for example, an alpha, beta-unsaturated ketone, aldehyde or carboxylic ester.
• ARP Amine Reaction Product
• PRMs typically PRMs that contain a ketone moiety and/or an aldehyde moiety
• the reactive amines are primary and/or secondary amines, and may be part of a polymer or a monomer (non-polymer).
• ARPs may also be mixed with additional PRMs to provide benefits of polymer-assisted delivery and/or amine-assisted delivery.
• Non-limiting examples of polymeric amines include polymers based on polyalkylimines, such as polyethyleneimine (PEI), or polyvinylamine (PVAm).
• Non-limiting examples of monomelic (non-polymeric) amines include hydroxyl amines, such as 2- aminoethanol and its alkyl substituted derivatives, and aromatic amines such as anthranilates.
• the ARPs may be premixed with perfume or added separately in leave-on or rinse-off applications.
• a material that contains a heteroatom other than nitrogen, for example oxygen, sulfur, phosphorus or selenium may be used as an alternative to amine compounds.
• the aforementioned alternative compounds can be used in combination with amine compounds.
• a single molecule may comprise an amine moiety and one or more of the alternative heteroatom moieties, for example, thiols, phosphines and selenols.
• the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in perfume delivery systems at levels, based on total perfume delivery system weight, of from 0.001 % to about 50%, from 0.005% to 30%, from 0.01% to about 10%, from 0.025% to about 5%, or even from 0.025% to about 1 %.
• the perfume delivery systems disclosed herein are suitable for use in consumer products, cleaning and treatment compositions, fabric and hard surface cleaning and/or treatment compositions, detergents, and highly compacted consumer products, including highly compacted fabric and hard surface cleaning and/or treatment compositions (e.g. , solid or fluid highly compacted detergents) at levels, based on total consumer product weight, from about 0.001 % to about 20%, from about 0.01 % to about 10%, from about 0.05% to about 5%, from about 0.1 % to about 0.5%.
• highly compacted fabric and hard surface cleaning and/or treatment compositions e.g. , solid or fluid highly compacted detergents
• the amount of PRMs from Table 1 present in the perfume delivery systems may be from about 0.1 % to about 99%, from 25% to about 95%, from 30 to about 90%, from 45% to about 90%, or from 65% to about 90%.
• microcapsules and/or nanocapsules may comprise one or more PRMs selected from Table 1 PRMs Nos. 1 and 2; stereoisomers of Table 1 PRMs Nos. 1 and 2 and mixtures thereof.
• the amount of total perfume based on total weight of starch encapsulates and starch agglomerates ranges from 0.1 % to about 99%, from 25% to about 95%, from 30 to about 90%, from 45% to about 90%, from 65% to about 90%.
• the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such starch encapsulates and starch agglomerates. Such PRMs and stereoisomers thereof may be used in combination in such starch encapsulates and starch agglomerates.
• the amount of total perfume based on total weight of [cyclodextrin - perfume] complexes ranges from 0.1 % to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 5% to about 25%.
• the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such [cyclodextrin - perfume] complexes. Such PRMs and stereoisomers thereof may be used in combination in such [cyclodextrin - perfume] complexes.
• the amount of total perfume based on total weight of Polymer Assisted Delivery (PAD) Matrix Systems ranges from 0.1 % to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 5% to about 25%. In one aspect, the amount of total perfume based on total weight of a hot melt perfume delivery system/perfume loaded plastic Matrix System and ranges from 1 % to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 10 % to about 50%.
• PAD Polymer Assisted Delivery
• the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such Polymer Assisted Delivery (PAD) Matrix Systems, including hot melt perfume delivery system/perfume loaded plastic Matrix Systems.
• PAD Polymer Assisted Delivery
• Such PRMs and stereoisomers thereof may be used in various combinations in such Polymer Assisted Delivery (PAD) Matrix Systems
• the amount of total perfume based on total weight of Amine Assisted Delivery (AAD) ranges from 1% to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 5% to about 25%.
• the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such Amine Assisted Delivery (AAD) systems. Such PRMs and stereoisomers thereof may be used in various combinations in such Amine Assisted Delivery (AAD) systems.
• an Amine Assisted Delivery (AAD) system may comprise one or more PRMs, and stereoisomers thereof, selected from Table 1 PRMs Nos. 1 and 2 and mixtures thereof.
• the amount of total perfume based on total weight of Amine Reaction Product ranges from 1% to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 5% to about 25%.
• the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such Amine Reaction Product (ARP) systems. Such PRMs and stereoisomers thereof may be used in various combinations in such Amine
• an Amine Reaction Product (ARP) system may comprise one or more PRMs, and stereoisomers thereof, selected from Table 1 PRM No. 2 and mixtures thereof.
• an Amine Reaction Product (ARP) system may comprise one or more PRMs, and stereoisomers thereof, selected from Table 1 PRM No. 2 and mixtures thereof.
• perfume delivery technologies a.k.a., perfume delivery systems
• perfume delivery systems that are disclosed in the present specification may be used in any combination in any type of consumer product, cleaning and/or treatment composition, fabric and hard surface cleaning and/or treatment composition, detergent, and/or highly compact detergent.
• the PRMs disclosed in Table 1 may be used to formulate perfumes. Such perfumes are combinations of PRMs that may comprise a combination of Table 1 PRMs, or one or more Table 1 PRMs and one or more additional PRMs. When used in a perfume, the Table 1 PRMs may be employed, based on total perfume weight, at levels of from about 0.01% to about 50%, from about 0.1% to about 15%, from about 0.1% to about 10% or even from about 0.5% to about 10%. Such perfumes may be utilized in various applications, including being applied neat to a situs or used in a consumer product, cleaning and/or treatment composition, fabric and hard surface cleaning and/or treatment composition, detergent, and/or a highly compact detergent.
• adjuncts are suitable for use in the compositions detailed herein (e.g. , consumer products, cleaning and/or treatment compositions, fabric and hard surface cleaning and/or treatment compositions, detergents, and/or a highly compact detergents).
• Such adjunct materials may be desirably incorporated in certain embodiments of the compositions, for example to assist or enhance performance of the composition, for treatment of the substrate to be cleaned, or to modify the aesthetics of the composition as is the case with perfumes, colorants, dyes or the like. It is understood that such adjuncts are in addition to the components that are supplied via Applicants' perfumes and/or perfume systems detailed herein.
• adjunct materials include, but are not limited to, surfactants, builders, chelating agents, dye transfer inhibiting agents, dispersants, enzymes, and enzyme stabilizers, catalytic materials, bleach activators, polymeric dispersing agents, clay soil removal/anti-redeposition agents, brighteners, suds suppressors, dyes, additional perfume and perfume delivery systems, structure elasticizing agents, fabric softeners, carriers, hydrotropes, processing aids and/or pigments, metal salts, structurants or binders, anti-tartar agents, anti-caries agents, abrasives, fillers, humectants, breath agents, flavors, antibacterial agents.
• suitable examples of such other adjuncts and levels of use are found in U.S. Patent No. 5,576,282, 6,306,812 B l , and 6,326,348 B l
• adjunct ingredient is not essential to Applicants' compositions.
• certain embodiments of Applicants' compositions may not contain one or more of the following adjuncts materials: bleach activators, surfactants, builders, chelating agents, dye transfer inhibiting agents, dispersants, enzymes, and enzyme stabilizers, catalytic metal complexes, polymeric dispersing agents, clay and soil removal/anti-redeposition agents, brighteners, suds suppressors, dyes, additional perfumes and perfume delivery systems, structure elasticizing agents, fabric softeners, carriers, hydrotropes, processing aids and/or pigments, metal salts, structurants or binders, anti- tartar agents, anti-caries agents, abrasives, fillers, humectants, breath agents, flavors, antibacterial agents.
• adjuncts may be present as detailed below:
• compositions according to the present invention can comprise a surfactant or surfactant system wherein the surfactant can be selected from nonionic and/or anionic and/or cationic surfactants and/or ampholytic and/or zwitterionic and/or semi -polar nonionic surfactants.
• the surfactant is typically present at a level of from about 0.1%, from about 1%, or even from about 5% by weight of the cleaning compositions to about 99.9%, to about 80%, to about 35%, or even to about 30% by weight of the cleaning compositions.
• compositions of the present invention can comprise one or more detergent builders or builder systems. When present, the compositions will typically comprise at least about 1% builder, or from about 5% or 10% to about 80%, 50%, or even 30% by weight, of said builder.
• Builders include, but are not limited to, the alkali metal, ammonium and
• compositions herein may also optionally contain one or more copper, iron and/or manganese chelating agents. If utilized, chelating agents will generally comprise from about 0.1% by weight of the compositions herein to about 15%, or even from about 3.0% to about 15% by weight of the compositions herein.
• Dye Transfer Inhibiting Agents The compositions of the present invention may also include one or more dye transfer inhibiting agents.
• Suitable polymeric dye transfer inhibiting agents include, but are not limited to, polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, polyvinyloxazolidones and polyvinylimidazoles or mixtures thereof.
• the dye transfer inhibiting agents are present at levels from about 0.0001%, from about 0.01%, from about 0.05% by weight of the cleaning compositions to about 10%, about 2%, or even about 1% by weight of the cleaning compositions.
• Dispersants - The compositions of the present invention can also contain dispersants.
• Suitable water-soluble organic materials are the homo- or co-polymeric acids or their salts, in which the polycarboxylic acid may comprise at least two carboxyl radicals separated from each other by not more than two carbon atoms.
• Enzymes - The compositions can comprise one or more detergent enzymes which provide cleaning performance and/or fabric care benefits.
• suitable enzymes include, but are not limited to, hemicellulases, peroxidases, proteases, cellulases, xylanases, lipases,
• phospholipases esterases, cutinases, pectinases, keratanases, reductases, oxidases,
• phenoloxidases lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, ⁇ - glucanases, arabinosidases, hyaluronidase, chondroitinase, laccase, and amylases, or mixtures thereof.
• a typical combination is a cocktail of conventional applicable enzymes like protease, lipase, cutinase and/or cellulase in conjunction with amylase.
• Enzyme Stabilizers - Enzymes for use in compositions for example, detergents can be stabilized by various techniques.
• the enzymes employed herein can be stabilized by the presence of water-soluble sources of calcium and/or magnesium ions in the finished
• compositions that provide such ions to the enzymes.
• Catalytic Metal Complexes - Applicants' compositions may include catalytic metal complexes.
• One type of metal-containing bleach catalyst is a catalyst system comprising a transition metal cation of defined bleach catalytic activity, such as copper, iron, titanium, ruthenium, tungsten, molybdenum, or manganese cations, an auxiliary metal cation having little or no bleach catalytic activity, such as zinc or aluminum cations, and a sequestrate having defined stability constants for the catalytic and auxiliary metal cations, particularly
• compositions herein can be catalyzed by means of a manganese compound.
• a manganese compound Such compounds and levels of use are well known in the art and include, for example, the manganese-based catalysts disclosed in U.S. patent 5,576,282.
• Cobalt bleach catalysts useful herein are known, and are described, for example, in U.S. patents 5,597,936.
• compositions herein may also suitably include a transition metal complex of a macropolycyclic rigid ligand - abbreviated as "MRL".
• MRL macropolycyclic rigid ligand
• the compositions and cleaning processes herein can be adjusted to provide on the order of at least one part per hundred million of the benefit agent MRL species in the aqueous washing medium, and may provide from about 0.005 ppm to about 25 ppm, from about 0.05 ppm to about 10 ppm, or even from about 0.1 ppm to about 5 ppm, of the MRL in the wash liquor.
• Suitable transition-metals in the instant transition-metal bleach catalyst include manganese, iron and chromium.
• Suitable MRL's herein are a special type of ultra-rigid ligand that is cross- bridged such as 5, 12-diethyl-l ,5,8,12-tetraazabicyclo[6.6.2]hexa-decane.
• Suitable transition metal MRLs are readily prepared by known procedures, such as taught for example in and U.S. patent 6,225,464.
• Some of the consumer products disclosed herein can be used to clean and/or treat a situs inter alia a surface or fabric.
• a situs is contacted with an embodiment of Applicants' composition, in neat form or diluted in a liquor, for example, a wash liquor and then the situs may be optionally washed and/or rinsed.
• a situs is optionally washed and/or rinsed, contacted with a composition according to the present invention and then optionally washed and/or rinsed.
• the situs is dried in a dryer, and/or passivel dried, for example, by line drying after the aforementioned cleaning and/or treating.
• washing includes but is not limited to, scrubbing, and mechanical agitation.
• the fabric may comprise most any fabric capable of being laundered or treated in normal consumer use conditions. Liquors that may comprise the disclosed
• compositions may have a pH of from about 3 to about 11.5. Such compositions are typically employed at concentrations of from about 500 ppm to about 15,000 ppm in solution.
• the wash solvent is water
• the water temperature typically ranges from about 5 °C to about 90 °C and, when the situs comprises a fabric, the water to fabric ratio is typically from about 1 : 1 to about 30: 1.
• logP logP
• ClogP The "calculated logP” (ClogP) is determined by the fragment approach of Hansch and Leo ( cf., A. Leo, in Comprehensive Medicinal Chemistry, Vol. 4, C. Hansch, P. G. Sammens, J. B. Taylor and C. A. Ramsden, Eds., p. 295, Pergamon Press, 1990, incorporated herein by reference). The fragment approach is based on the chemical structure of each perfume ingredient, and takes into account the numbers and types of atoms, the atom connectivity, and chemical bonding.
• the ClogP values which are the most reliable and widely used estimates for this physicochemical property, are preferably used instead of the experimental logP values in the selection of perfume ingredients which are useful in the present invention.
• Boiling point is measured by ASTM method D2887-04a, "Standard Test Method for Boiling Range Distribution of Petroleum Fractions by Gas Chromatography," ASTM International.
• perfume content of 25wt% in the aqueous slurry perfume content of 25wt% in the aqueous slurry.
• the Headspace Ratio for determining perfume leakage from a perfume delivery system is defined as the headspace concentration of Sample A divided by the headspace concentration of Sample _ A
• Hs amp ie_B is the headspace concentration of a consumer product formulation Sample B.
• the Headspace Ratio for determining perfume delivery efficiency from a perfume delivery system is defined as the headspace concentration of Sample B divided by the headspace
• Hs amp ie_B is the headspace concentration of a consumer product formulation Sample B.
• Solid-Phase Micro-Extraction (SPME)-Gas Chromatography/Mass Spectrometry is used to measure the level of perfume raw materials in the headspace of products. 1.0 grams of the 1 week at 40 degrees Centigrade aged sample are placed into a clean 20 ml headspace vial and allowed to equilibrate for at least 2 hours at room temperature. The samples are then analyzed using the MPS2-SMPE-GC-MS analysis system (GC-
• GC Gas Chromatograph
• the injector liner is a special SPME liner (0.75 mm ID) from Supelco.
• the Detector is a model 5973 Mass Selective Detector obtained from Agilent Technologies, Inc., Wilmington, DE, USA having a source temperature of about 230 °C, and a MS Quad temperature of about 150 °C.
• the SPME fiber assembly is DVB/CAR/PDMS (50/30 urn, 24 ga, 1 cm length). Sampling time is 5 minutes.
• Injector temperature is at 260C.
• Perfume compounds are identified using the MS spectral libraries of John Wiley & Sons and the National Institute of Standards and Technology (NIST), purchased and licensed through Hewlett Packard.
• the ratio for each PRM is calculated by dividing the peak area for the perfume raw
• the Headspace Ratio is calculated as the sum of the individual perfume raw material ratios obtained in step 9. (4) Perfume leakage can also be evaluated via% liquid-liquid extraction and gas
• % perfume leakage ((Area Perfume Raw Material caps x Area Internal Standard Solution ref x Weight ref) / (Area Internal Standard Solution caps x Area Perfume Raw Material ref x Weight caps)) x 100 (5) Odor Detection Threshold (OPT)
• the gas chromatograph is calibrated to determine the exact volume of material injected by the syringe, the precise split ratio, and the hydrocarbon response using a hydrocarbon standard of known concentration and chain length distribution.
• the air flow rate is accurately measured and, assuming the duration of human inhalation to last 12 seconds, the sampled volume is calculated. Since the precise concentration at the detector at any point in time is known, the mass per volume inhaled is known, and hence the concentration of material.
• solutions are delivered to the sniff port at the calculated concentration.
• a panelist sniffs the GC effluent and identifies the retention time when odor is noticed. The average among 6 panelists determines the threshold of notice ability.
• the necessary amount of analyte is injected into the column to achieve a 50 parts per billion concentration at the detector. Typical gas
• Length 30 meters, 0.25millmeter inside diameter, 1 micrometer film thickness
• the reaction mixture changed to a yellow colour.
• the internal temperature was reduced to -24°C and to the clear yellow solution was added methyl chloroformate (41.2 g, 99%, 432 mmol, 0.95 eq) over two hours via a syringe using a syringe pump. During the addition the internal temperature rose from -24°C to -17°C.
• the reaction mixture changed progressively from a clear yellow solution to a cloudy yellow suspension.
• the reaction mixture was stirred for 2h30 while allowing the internal temperature to rise from -17°C to +7°C.
• the reaction mixture was diluted with ethyl acetate (1.5 L).
• the organic phase was then washed with water (7 x 1 L) till a GC analysis of the organic phase indicated the complete absence of 2.
• the organic phase was concentrated under reduced pressure (45 °C, 100 mbar -> 3 mbar) to obtain the crude 1 as a viscous yellow oil (55.76 g, 98.0% pure by GC).
• the crude was flash distilled (111-152°C pot, 93-95°C vapour, 0.6 mbar) to obtain 1 as a very pale yellow viscous liquid (55.3 g, 98.5% pure by GC; 63% yield).
• Example 3 84wt% Core / 16wt% Wall Melamine Formaldehyde (MF) Capsule (PAD Reservoir
• Example 4 Process of Making a Polymer Assisted Delivery (PAD) Matrix System
• a mixture comprising 50% of a perfume composition comprising one or more Table 1 PRMs, 40% of carboxyl-terminated HyproTM RLP 1300X18 (CAS#0068891-50-9) from nanoresins, (put at 60°C in warm water bath for 1 hour before mixing) and 10% of Lupasol® WF(CAS# 09002-98-6) from BASF ( put at 60°C in warm water bath for 1 hour before mixing).
• Mixing is achieved by mixing for five minutes using a Ultra-Turrax T25 Basic equipment (from IKA). After mixing, the mixture is put in a warm water bath at 60°C for + 12 hours. A homogenous, viscous and sticky material is obtained.
• Examples 5-35 Product Formulation Non-limiting examples of product formulations containing PRMs disclosed in the present specification perfume and amines summarized in the following table. Examples 5 - 10
• Granular laundry detergent compositions for hand washing or washing machines typically top- loading washing machines.
• One or more materials comprising an amine moiety as disclosed in the present specification.
• Granular laundry detergent compositions typically for front-loading automatic washing machines.
• Perfume comprising one or more PRMs 0.3 0.4 0.01 0.02 0.04 0.1 from Table 1
• the typical pH is about 10.
• Hydrogenated castor oil derivative 0.1 0.1 structurant 0 0 0 0 0 0 0 0
• Xyloglucanase (Whitezyme®, 0.2 20mg active/g) 0.2 0.1 0 0 0.05 0.05
• Lipex® (18 mg active/g) 0.4 0.2 0.3 0.1 0.2 0 0
• Perfume comprising one or more 0.7 0.5 0.8 0.05 0.6 0.1 0.6 PRMs from Table 1
• Amylase (30mg/g - - - 0.02 active)
• Perfume comprising 0.3 0.4 0.01 0.02 0.04 0.1 one or more PRMs
• balan balanc balanc bala ce ce ce ce e e nee
• One or more materials comprising an amine moiety as disclosed in the present specification.
• optional agents/components include suds suppressors, structuring agents such as those based on Hydrogenated Castor Oil (preferably Hydrogenated Castor Oil, Anionic Premix), solvents and/or Mica pearlescent aesthetic enhancer.
• LAS is linear alkylbenzenesulfonate having an average aliphatic carbon chain length C9-C15 supplied by Stepan, Northfield, Illinois, USA or Huntsman Corp. (HLAS is acid form).
• AE3S is C 12-15 alkyl ethoxy (3) sulfate supplied by Stepan, Northfield, Illinois, USA
• AE7 is C 12-15 alcohol ethoxylate, with an average degree of ethoxylation of 7, supplied by Huntsman, Salt Lake City, Utah, USA
• AES is C 10-18 alkyl ethoxy sulfate supplied by Shell Chemicals.
• AE9 is C 12-13 alcohol ethoxylate, with an average degree of ethoxylation of 9, supplied by Huntsman, Salt Lake City, Utah, USA
• HSAS or HC1617HSAS is a mid-branched primary alkyl sulfate with average carbon chain length of about 16-17
• Zeolite A is supplied by Industrial Zeolite (UK) Ltd, Grays, Essex, UK 1.6R Silicate is supplied by Koma, Nestemica, Czech Republic
• Polyacrylate MW 4500 is supplied by BASF, Ludwigshafen, Germany
• Carboxymethyl cellulose is Finnfix® V supplied by CP Kelco, Arnhem, Netherlands
• Suitable chelants are, for example, diethylenetetraamine pentaacetic acid (DTP A) supplied by
• Savinase®, Natalase®, Stainzyme®, Lipex®, CellucleanTM, Mannaway® and Whitezyme® are all products of Novozymes, Bagsvaerd, Denmark.
• Proteases may be supplied by Genencor International, Palo Alto, California, USA (e.g.
• Fluorescent Brightener 1 is Tinopal® AMS
• Fluorescent Brightener 2 is Tinopal® CBS-X
• Sulphonated zinc phthalocyanine and Direct Violet 9 is Pergasol® Violet BN-Z all supplied by Ciba Specialty Chemicals, Basel, Switzerland
• Sodium perborate is supplied by Degussa, Hanau, Germany
• NOBS is sodium nonanoyloxybenzenesulfonate, supplied by Future Fuels, Batesville, USA
• TAED is tetraacetylethylenediamine, supplied under the Peractive® brand name by Clariant GmbH, Sulzbach, Germany
• S-ACMC is carboxymethylcellulose conjugated with C.I. Reactive Blue 19, sold by
• Soil release agent is Repel-o-tex® PF, supplied by Rhodia, Paris, France
• Acrylic Acid/Maleic Acid Copolymer is molecular weight 70,000 and acrylate:maleate ratio 70:30, supplied by BASF, Ludwigshafen, Germany
• HEDP Hydroxyethane di phosphonate
• HSAS is mid-branched alkyl sulfate as disclosed in US 6,020,303 and US 6,060,443
• Random graft copolymer is a polyvinyl acetate grafted polyethylene oxide copolymer having a polyethylene oxide backbone and multiple polyvinyl acetate side chains.
• the molecular weight of the polyethylene oxide backbone is about 6000 and the weight ratio of the polyethylene oxide to polyvinyl acetate is about 40:60 and no more than 1 grafting point per 50 ethylene oxide units.
• Cationic cellulose polymer is LK400, LR400 and/or JR30M from Amerchol Corporation, Edgewater NJ
• Perfume comprising one or more 0.60

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