Patent Application
20170204223
The delayed and sustained release of fragrance ingredients is a sought-after property to extend the benefit of fragrance in many consumer applications. Typically neat fragrance oils have a limited performance duration due to the volatile nature of the materials. Encapsulation technologies seek to entrap the fragrance ingredients inside supramolecular structures; however some of these technologies are limited to use of fragrance ingredients that will not react with the encapsulation components themselves, e.g., free amine groups in polyurea capsules.
Approaches for cross-linking fragrances to gel polymers, copolymerization or trapping fragrances within polymeric matrices have been described. See, U.S. Pat. No. 7,700,665, WO 2012/071261, and WO 2010/094356. Further, co-delivery of fragrances with polyoxyalkylene amines has been suggested. See WO 2009/065738. In addition, the use of a modified amino-functional polymer or polyvinylamine in the production of a pro-fragrance compound has been described. See WO 2009/153209 and US 2006/0204462.
One aspect of this invention relates to a fragrance adduct that is a reaction product between a polymeric amine and a reactive fragrance ingredient, in which the polymeric amine has a molecular weight of 100 to 10,000,000 Daltons (e.g., 100 to 10000 and 200 to 5000) and contains a backbone and at least one amino functional group; the reactive fragrance ingredient is an aldehyde, a ketone, an α,β-unsaturated electrophilic compound reactive towards the polymeric amine, or a combination thereof, and the reaction product is an imine compound or a Michael addition adduct.
In the polymeric amine, the backbone can be polyalkylene or polyoxyalkyleneamine. Example of the polymeric amine includes polyoxyalkyleneamine containing propylene oxide, ethylene oxide, butylene oxide or a mixture thereof, and the following compounds:
In preferred embodiments, the polymeric amine is
Turning to the reactive fragrance ingredient, it is a aldehyde, a ketone, an α,β-unsaturated carbonyl compound, an α,β-unsaturated nitrile, an α,β-unsaturated nitroxide, or a combination thereof. These compounds are reactive towards the polymeric amines. In some embodiments, the fragrance adduct is an imine formed between the polymeric amines and the reactive fragrance ingredient selected from the group consisting of aldehydes, ketones, and combinations thereof. In other embodiments, the fragrance adduct is a Michael addition adduct formed between the polymeric amine and the fragrance ingredient selected from the group consisting of β,β-unsaturated carbonyl compounds, α,β-unsaturated nitriles, α,β-unsaturated nitroxides, and combinations thereof
Examples of the reactive fragrance ingredient is 6-decenal, 3-(4-isobutylcyclohexyl)propanal, 2-octahydro-1H-4,7-methanoinden-5-yl)acetaldehyde, 2-methylpentan-3-yl (E)-but-2-enoate, 4-(heptyloxy)-3-methylbutanal, 7,7,8,9,9-pentamethyl-6,7,8,9-tetrahydro-5H-cyclopenta[h]quinazoline, or a combination thereof.
Another aspect of this invention relates to a fragrance composition comprising the fragrance adduct described above.
Also within the scope of this invention is a household product, personal care product, hair care product or beauty care product comprising the fragrance adduct described above.
Still within the scope of this invention is a method for sequestering a fragrance comprising binding a fragrance to a polymeric amine to form a fragrance adduct thereby sequestering the fragrance, wherein the fragrance is a an aldehyde, a ketone, an α,β-unsaturated electrophilic compound reactive towards the polymeric amine, or a combination thereof. The fragrance adduct can react with a malodor acid or malodor thiol compound thereby releasing the fragrance from the fragrance adduct.
The details of one or more embodiments of the invention are set forth in the description below. Other features, objects, and advantages of the invention will be apparent from the description and the claims.
Aldehydes are generally not suitable for use in conventional polyurea capsule delivery systems due to reactivity with the wall forming components of the system. It has now been found that a polymeric di-, tri- or polyamine, generally referred to herein as an “polymer,” can be reacted with a fragrance ingredient that is an aldehyde, ketone, or α,β-unsaturated electrophilic compound (e.g., an alpha-beta unsaturated carbonyl compound) to sequester the fragrance ingredient.
More specifically, one or more free amine functional groups of the polymer react with either a carbonyl of the fragrance to form an imine (Scheme 1), or an alpha-beta unsaturated carbonyl compound to form a Michael addition adduct (Scheme 2) thereby forming the fragrance adduct.
The polymer can be mixed with either a single fragrance ingredient first, or a mixture of materials containing a plurality of different fragrance ingredients. The resulting imine or Michael addition adduct composition can then be used in a fragrance accord as a delayed delivery system, which slowly releases the sequestered fragrance ingredient under mildly acidic conditions with water or moisture to provide lasting fragrance performance as well as malodor control.
Accordingly, the present invention provides fragrance adducts and delivery compositions and methods for sequestering fragrance ingredients using a polymeric amine. In particular, the fragrance adduct of the invention is an imine or Michael adduct formed between a reactive fragrance ingredient and a polymeric amine. The reactive fragrance ingredient is selected from the group consisting of aldehydes, ketones, an alpha,beta-unsaturated electrophilic compounds (e.g., alpha,beta-unsaturated carbonyl compounds).
As used herein, the tern “polymer” as used herein refers to a compound having two or more repetitive units. As such, polymers also include oligomers, which have two to ten repetitive units.
Water soluble diamines are one class of polymeric amines of use in this invention such as:
H2N(CH2)nNH2,
where n is >1 (e.g., 2 to 1,000,000 and 10 to 500,000). Exemplary amines of this type include, but are not limited to, 1,3-diaminopropane, 1,4-diaminobutane, hexanethylene diamine, hexamethylene diamine, and pentaethylenehexamine.
Polymeric amines that have a functionality greater than 2 include polyalkylene polyamines of the type:
where R is hydrogen or —CH3, m is 1-5 and n is 1-5, e.g., diethylene triamine, triethylene tetraamine and the like. Exemplary amines of this type include, but are not limited to diethylenetriamine, bis(3-aminopropyl)amine, bis(hexanethylene)triamine.
In particular embodiments, the polymeric amine is a polyoxyalkyleneamine. Polyoxyalkyleneamines include two of more primary or secondary amino groups attached to a backbone, derived, for example, from propylene oxide, ethylene oxide, butylene oxide or a mixture thereof. The ether amine can be monoamine, diamine, or triamine, based on this core structure. An example is:
Exemplary polyoxyalkyleneamines include 2,2′-ethylenedioxy)bis (ethylamine) and 4,7,10-trioxa-1,13-tridecanediamine, as well as those available under the designation JEFFAMINE, such as, without limitation, JEFFAMINE D-230, D-400, D-2000, HK-511, ED-600, ED-900, ED-2003, T-403, T-3000, T-5000, SD-231, SD-401, SD-2001, and ST-404 (Huntsman Corporation). Such amines have an approximate molecular weight ranging from 200 to 7500.
Other suitable amines include, but are not limited to, tris(2-aminoethyl)amine, triethylenetetramine, N,N′-bis(3-aminopropyl)-1,3-propanediamine, tetraethylene pentamine, 1,2-diaminopropane, N,N,N′,N′-tetrakis(2-hydroxyethyl)ethylene diamine, N,N,N′,N′-tetrakis(2-hydroxypropyl)ethylene diamine, branched polyethylenimine, 2,4-diamino-6-hydroxypyrimidine and 2,4,6-triaminopyrimidine.
Fragrances that can be sequestered with the polymers described herein include, but are not limited to, individual fragrances, any combination of fragrance oils, essential oils, plant extracts or mixture thereof, which contain an aldehyde, ketone, or an alpha-beta unsaturated carbonyl functional group. Exemplary ketones include, but are not limited to buchu oxime; isojasmone; methyl-β-naphthyl ketone, musk indanone; tonalide/musk plus; α-damascone, β-damascone, δ-damascone, isodamascone, damascenone, damarose, methyl dihydrojasmonate, menthone, carvone, camphor, fenchone, α-ionene, β-ionone, dihydro-β-ionone, γ-methyl so-called ionone, fleuramone, dihydrojasmone, cis-jasmone, iso-E-super, methyl cedrenyl ketone or methyl cedrylone, acetophenone, methyl acetophenone, paramethoxyacetophenone, methyl-β-naphthyl ketone, benzylacetone, benzophenone, parahydroxy-phenylbutanone, celery ketone or livescone, 6-isopropyl-decahydro-2-naphthone, dimethyloctenone, freskomenth, 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone, methylheptenone, 2-(2-(4-methyl-3-cyclohexen-1-yl)propyl)cyclopentanone, 1-(p-menthen-6(2)-yl)-1-propanone, 4-(4-hydroxy-3-methoxyphenyl)-2-butanone, 2-acetyl-3,3-dimethylnorbornane, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)indanone, 4-damascole, dulcinyl or cassion, gelsone, hexalone isocyclemon E, methyl cyclocitron, methyl lavendel ketone, orivone, para-tert-butylcyclohexanone, verdone, delphone, muscone, neobutenone, plicatone, veloutone, 2,4,4,7-tetramethyloct-6-en-3-one, tetramerane, hedione, and mixtures thereof. The ketones may preferably be selected from α-damascone, δ-damascone isodamascone, carvone, γ-methylionone, iso-E-super, 2,4,4,7-tetramethyloct-6-en-3-one, benzylacetone, β-damascone, damascenone, methyl dihydrojasmonate, methyl cedrylone, hedione and mixtures thereof.
Suitable fragrances containing aldehydes include individual aldehydes or aldehyde mixtures such as, for example, melonal, triplal, ligustral, adoxal, anisaldehyde, cymal, ethyl vanillin, florhydral, helional, heliotropin, hydroxycitronellal, koavone, lauryl aldehyde, lyral, methyl nonylacetaldehyde, p,t-bucinal, phenyl acetaldehyde, undecylene aldehyde, vanillin, 2,6,10-trimethyl-9-undecenal, 3-dodecen-1-al, α-n-amylcinnamaldehyde, 4-methoxybenzaldhyde, benzaldehyde, 3-(4-tert-butylphenyl)propanal, 2-methyl-3-(para-methoxyphenylpropanal), 2-methyl-4-(2,6,6trimethyl-2(1)-cyclohexen-1-yl)butanal, 3-phenyl-2-propenal, cis-/trans-3,7-dimethyl-2,6-octadien-1-al, 3,7-dimethyl-6-octen-1-al, [(3,7-dimethyl-6octenyl)oxy]acetaldehyde, 4-isopropylbenzaldehyde, 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthaldehyde, 2,4-dimethyl-3-cyclohexen-1-carboxyaldehyde, decylaldehyde, 2,6-dimethyl-5-heptenal; 4-(tricyclo(5.2.1.0(2,6)]decylidene-8)butanal, octahydro-4,7-methano-IH-indenecarboxaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, para-ethyl-β,α-dimethylhydrocinnamaldehyde, α-methyl-3,4(methylenedioxy)hydrocinnamaldehyde, 3,4-methylenedioxybenzaldehyde, α-n-hexylcinnamaldehyde, m-cymene-7-carboxaldehyde, α-methyl-phenylacetaldehyde, 7-hydroxy-3,7-dimethyloctanal, undecenal, 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 4-(3)(4-methyl-3-pentenyl)-3 cyclohexene carboxaldehyde, 1-dodecanal, 2,4-dimethylcyclohexene-3-carboxaldehyde, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbox-aldehyde, 7-methoxy-3,7-dimethyloctan-1-al, 2-methylundecanal, 2-methyldecanal, 1-nonanal, 1-octanal, 2,6,10-trimethyl-5,9-undecadienal, 2-methyl-3-(4-tert-butyl)propanal, dihydrocinnamaldehyde, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxaldehyde, 5- or 6-methoxyhexahydro-4,7-methanoindan-1- or 2-carboxyaldehyde, 3,7-dimethyloctan-1-al, 1-undecanal, 10-undecen-1-al, 4-hydroxy-3methoxybenzaldehyde, 1-methyl-3-(4-methylpentyl)-3-cyclohexenecarboxyaldehyde, 7-hydroxy-3,7dimethyloctanal, trans-4-decenal, 2,6-nonadienal, para-tolylacetaldehyde, 4-methylphenylacetaldehyde, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal, ortho-methoxycinnamaldehyde, 3,7-dimethyl-2-methylene-6-octenal, phenoxyacetaldehyde, 5,9-dimethyl-4,8-decadienal, peony aldehyde (6,10-dimethyl-3-oxa-5,9-undecadien-1-al), hexahydro-4,7-methanoindane-1-carboxaldehyde, 2-methyloctanal, α-methyl-4-(1-nnethylethyl)benzeneacetaldehyde, 6,6-dimethyl-2-norpinene-2-propionaldehyde, para-methylphenoxyacetaldehyde, 2-methyl-3-phenyl-2-propen-1-al, 3,5,5-trimethylhexanal, hexahydro-8,8-dimethyl-2-naphthaldehyde, 3-propylbicyclo[2.2.1]-hept-5-ene-2-carbaldehyde, 9-decenal, 3-methyl-5-phenyl-1-pentanal, methylnonylacetaldehyde, 1-p-menthene-q-carboxaldehyde, citral or mixtures thereof, lilial citral, 1-decanal, florhydral, or 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde. Preferred aldehydes may be selected from cis/trans-3,7-dimethyl-2,6octadien-1-al, heliotropin, 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 2,6-nonadienal, α-n-amylcinnamaldehyde, α-n-hexylcinnamaldehyde, p-tert-bucinal, lyral, cymal, methyl-nonylacetaldehyde, trans-2-nonenal, lilial, trans-2-nonenal and mixtures thereof.
In particular embodiments, the fragrance is 6-decenal (Opalene), 3-(4-isobutylcyclohexyl)propanal (Starfleur), 2-octahydro-1H-4,7-methanoinden-5-yl)acetaldehyde (Aquaflora), 2-methylpentan-3-yl (E)-but-2-enoate (Cosmofruit), 7,7,8,9,9-pentamethyl-6,6a,7,8,9,9a-hexahydro-5H-cyclopenta[h]quinazoline (Ambertonic), 4-(heptyloxy)-3-methylbutanal (Cristalfizz), 7,7,8,9,9-pentamethyl-6,7,8,9-tetrahydro-5H-cyclopenta[h]quinazoline (Sinfonide) 2-[(4-methylphenyl)methylene]-heptanal (Acalea), iso-amyl oxyacetic acid allylester (Allyl Amyl Glycolate), (3,3-dimethylcyclohexyl)ethyl ethyl propane-1,3-dioate (Applelide), (E/Z)-1-ethoxy-1-decene (Arctical), 2-ethyl-4-(2,2,3-trimethyl-3-cyclo-penten-1-yl)-2-buten-1-ol (Bacdanol), 2-methyl-3-[(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)oxy] exo-1-propanol (Bomafix), 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one (Cashmeran), trimethylcyclopentenylmethyloxabicyclooctane (Cassiffix), 1,1-dimethoxy-3,7-dimethyl-2,6-octadiene (Citral DMA), 3,7-dimethyl-6-octen-1-ol (Citronellol), 3A,4,5,6,7,7A-hexahydro-4,7-methano-1H-inden-5/6-yl acetate (Cyclacet), 3A,4,5,6,7,7A-hexahydro-4,7-methano-1H-inden-5/6-yl propinoate (Cyclaprop), 3A,4,5,6,7,7A-hexahydro-4,7-methano-1G-inden-5/6-yl butyrate (Cyclobutanate), 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-2-buten-1-one (Delta Damascone), 3-(4-ethylphenyl)-2,2-dimethyl propanenitrile (Fleuranil), 3-(O/P-ethylphenyl) 2,2-dimethyl propionaldehyde (Floralozone), tetrahydro-4-methyl-2-(2-methylpropyl)-2H-pyran-4-ol (Floriffol), 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-gamma-2-benzopyran (Galaxolide), 1-(5,5-dimethyl-1-cyclohexen-1-yl)pent-4-en-1-one (Galbascone), E/Z-3,7-dimethyl-2,6-octadien-1-yl acetate (Geranyl Acetate), α-methyl-1,3-benzodioxole-5-propanal (Helional), 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one (Hexalon), (Z)-3-hexenyl-2-hydroxybenzoate (Hexenyl Salicylate, CIS-3), 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (Ionone α), 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-ethan-1-one (Iso E Super), methyl 3-oxo-2-pentylcyclopentaneacetate (Kharismal), 2,2,4-trimethyl-4-phenyl-butanenitrile (Khusinil), 3,4,5,6,6-pentamethylhept-3-en-2-one (Koavone), 3/4-(4-hydroxy-4-methyl-pentyl) cyclohexene-1-carboxaldehyde (Lyral), 3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (Methyl Ionone γ), 1-(2,6,6-trimethyl-2-cyclohexen-1-yl) pent-1-en-3-one (Methyl Ionone α Extra, Methyl Ionone N), 3-methyl-4-phenylbutan-2-ol (Muguesia), cyclopentadec-4-en-1-one (Musk Z4), 3,3,4,5,5-pentamethyl-11,13-dioxatricyclo[7.4.0.0<2,6>]tridec-2(6)-ene (Nebulone), 3,7-dimethyl-2,6-octadien-1-yl acetate (Neryl Acetate), 3,7-dimethyl-1,3,6-octatriene (Ocimene), ortho-tolylethanol (Peomosa), 3-methyl-5-phenylpentanol (Phenoxanol), 1-methyl-4-(4-methyl-3-pentenyl) cyclohex-3-ene-1-carboxaldehyde (Precyclemone B), 4-methyl-8-methylene-2-adamantanol (Prismantol), 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol (Sanjinol), 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol (Santaliff), Terpineol, 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde (Triplal), decahydro-2,6,6,7,8,8-hexamethyl-2H-indeno[4,5-B]furan (Trisamber), 2-tert-butylcyclohexyl acetate (Verdox), 4-tert-butylcyclohexyl acetate (Vertenex), acetyl cedrene (Vertofix), 3,6/4,6-dimethylcyclohex-3-ene-1-carboxaldehyde (Vertoliff), and (3Z)-1-[(2-methyl-2-propenyl)oxy]-3-hexene (Vivaldie) or a mixtures thereof.
The imine or Michael adduct materials of the invention can be combined with each other and/or other malodor counteractant compounds, e.g., as described in U.S. Pat. No. 7,993,633; US 2013/0101544; US 2013/0101545 and US 2012/0294821.
The fragrance adduct and composition of the invention is of particular use in a method for sequestering a fragrance. In accordance with such a method, a polymeric amine and a reactive fragrance ingredient are reacted to form a fragrance adduct such as an imine compound or a Michael addition adduct. The fragrance adduct comprises a polymeric amine moiety and a reactive fragrance moiety. The two moieties are covalently bound to sequester the fragrance without the need for encapsulation. This method can be used to delay release of high impact aldehyde materials, which are reactive to the encapsulating materials. As such encapsulating these materials have not been previously available.
The fragrance adduct is then used in a fragrance accord as a delayed delivery system. Imines and Michael addition adducts are known to hydrolyze slowly in the presence of an acid and moisture (i.e., water), triggering the release of the sequestered fragrance ingredient.
Other unreactive fragrance ingredients can be adsorbed to the backbone of the polymeric amine or fragrance adduct via non-covalent attractive forces (H-bonding, etc) which alters the materials volatility. As such, in some embodiments, the fragrance adduct further comprises a second (third, fourth, fifth, or sixth) fragrance ingredient binding to the fragrance adduct via a non-covalent attractive force. This is an additional mechanism of delayed fragrance ingredient release. Taken altogether, the system has both chemically bonded and non-chemically bonded fragrance ingredients that have delayed fragrance release and malodor control.
Malodor acids, such as butyric and isovaleric, can be such acidic triggers to cause the hydrolysis and release of the fragrance ingredient. The resulting free amine is able to neutralize the malodor acid in an acid-base ion pair.
Moreover, in addition to the polymeric amine freed from the hydrolysis, unreacted amino groups of the polymeric amine can also neutralize a malodor acid or malodor thiol compound in a product. For the purposes of the present invention, a compound neutralizes a malodor if it measurably (either qualitatively or quantitatively) reduces the perception or intensity of a malodor. In particular embodiments, the polymeric amine reduces the perception or intensity of a malodor by 50-100% as compared to the malodor in the absence of the polymeric amine. When the polymeric amine is used in combination with a fragrance, the fragrance can result in a further reduction in the perception or intensity of a malodor. In particular embodiments, a polymeric amine of the invention reduces the perception or intensity of a malodor by at least 50, 55, 60, 65, 70, 75, 80, 85, 90, 95 or 100% as compared to the malodor in the absence of the polymeric amine.
The inventive imine or Michael adduct composition can be included in any fragrance oil or accord wherever such an application calls for such a use. Exemplary products include, but are not limited to, household products (laundry detergents, scent boosters, fabric conditioners, dish detergent, AP cleaners, room deodorizers, candles, etc); personal care products (bar soap/wash/gel, sunscreen, antiperspirant/deodorant, lotions, powders, toiletries, shave cream, etc); hair care products (shampoo, conditioner, rinses, styling products, etc); and beauty care (fine fragrance, solid perfume, foundations, eye shadow, lipstick, etc.).
In this respect, the composition of the invention can be in the form of an aerosol or other spray, fragrance diffusers, a wick or other liquid system, or a solid, for instance candles or a wax base as in pomanders and plastics, powders as in sachets or dry sprays or gels, as in solid gel sticks, clothes deodorants as applied by washing machine applications such as in detergents, powders, liquids, whiteners or fabric softeners, fabric refreshers, linen sprays, closet blocks, closet aerosol sprays, or clothes storage areas or in dry cleaning to overcome residual solvent notes on clothes, bathroom accessories such as paper towels, bathroom tissues, sanitary napkins, towelettes, disposable wash cloths, disposable diapers, and diaper pail deodorants, cleansers such as disinfectants and toilet bowl cleaners, cosmetic products such as antiperspirant and deodorants, general body deodorants in the form of powders, aerosols, liquids or solid, or hair care products such as hair sprays, conditioners, rinses, hair colors and dyes, permanent waves, depilatories, hair straighteners, hair groom applications such as pomade, creams and lotions, medicated hair care products containing such ingredients as selenium sulphide, coal tar or salicylates, or shampoos, or foot care products such as foot powders, liquids or colognes, after shaves and body lotions, or soaps and synthetic detergents such as bars, liquids, foams or powders, agricultural and pet care products such as domestic animal and pet care products including deodorants, shampoo or cleaning agents, or animal litter material. In addition, the composition can be used in a fine fragrance.
In some embodiments, the composition can be further encapsulated in a core-shell microcapsule. Encapsulation of active materials is known in the art, see for example U.S. Pat. Nos. 2,800,457, 3,870,542, 3,516,941, 3,415,758, 3,041,288, 5,112,688, 6,329,057, and 6,261,483. Wall forming materials include polyurethane, polysiloxanes, polyurea, polyamide, polyimide, polyvinyl alcohol, polyanhydride, polyolefin, polysulfone, polysaccharide, protein, polylactide (PLA), polyglycolide (PGA), polyorthoester, polyphosphazene, silicone, lipid, modified cellulose, gums, polystyrene, and polyesters or combinations of these materials. Other polymeric materials that are functional are ethylene maleic anhydride copolymer, styrene maleic anhydride copolymer, ethylene vinyl acetate copolymer, and lactide glycolide copolymer. Biopolymers that are derived from alginate, chitosan, collagen, dextran, gelatin, and starch can also be used as the encapsulating materials. Additionally, microcapsules can be made via the simple or complex coacervation of gelatin. Preferred encapsulating polymers include those formed from gelatin, urea-formaldehyde, melamine-formaldehyde, isocyanates, silica, or hydrogel-forming polymers.
In some embodiments, the composition of the invention is provided as a spray-dried composition. Suitable methods for spray drying are provided in, e.g., PCT/US2013/060290. Briefly, the practice involves dispersing and dissolving dry carrier materials (e.g., sugar, sugar derivatives, modified starch, proteins, celluloses, salts, dextrins, gums, sugar alcohols, polyols, peptides, acids, carbohydrates or hydrocolloids) in solvent until free of lumps. The composition is then added under constant agitation until a homogeneous mixture is obtained. The emulsion may be further subjected to high shear or homogenized to reduce oil droplet size prior to spray drying. Subsequently, the mixture or emulsion is spray-dried using any suitable spray dryer. For example, a spray dryer with a vertical parallel flow function can be used. The spray dryer should be a system with a dehumidifying and drying function. For example, a spray dryer capable of blowing a high volume of desiccated air with a dew point of less than 5° C. is particularly preferable. For a spray dryer with no dehumidifying and drying function, the spray dryer is inevitably arranged with a dry dehumidifier, e.g., a honeycomb-type rotary dehumidifier (e.g., Nichias Corporation or Sweden PROFLUTE Corporation). Suitable spray dryers include the micromist spray dryer and the hybrid granulator series manufactured by Fujisaki Electric Co., Ltd.; the fluidized spray dryer FSD with internal fluid bed as manufactured by Niro Corporation; the fluid granulation spray dryer and L-8 type spray dryer manufactured by Ogawara (Japan); the DL-21 type and GB-21 type spray dryers manufactured by Yamato Scientific Co., Ltd., and Anhydro Spray Bed Dryer manufactured by SPX Corporation. Once dried, desirably the composition contains from about 0% to about 15% water. Preferably, the composition will have a water activity of 0.1 to 0.6, or more desirably 0.2 to 0.5, and most preferably from 0.2 to 0.4 wherein said levels of dryness can be achieved with or without secondary drying.
The delivery systems of the present invention are well-suited for use, without limitation, in the following products:
The above-listed applications are all well known in the art. For example, fabric softener systems are described in U.S. Pat. Nos. 6,335,315, 5,674,832, 5,759,990, 5,877,145, 5,574,179; 5,562,849, 5,545,350, 5,545,340, 5,411,671, 5,403,499, 5,288,417, and 4,767,547, 4,424,134. Liquid laundry detergents include those systems described in U.S. Pat. Nos. 5,929,022, 5,916,862, 5,731,278, 5,565,145, 5,470,507, 5,466,802, 5,460,752, 5,458,810, 5,458,809, 5,288,431, 5,194,639, 4,968,451, 4,597,898, 4,561,998, 4,550,862, 4,537,707, 4,537,706, 4,515,705, 4,446,042, and 4,318,818. Liquid dish detergents are described in U.S. Pat. Nos. 6,069,122 and 5,990,065. Shampoo and conditioners that can employ the present invention include those described in U.S. Pat. Nos. 6,162,423, 5,968,286, 5,935,561, 5,932,203, 5,837,661, 5,776,443, 5,756,436, 5,661,118, 5,618,523, 5,275,755, 5,085,857, 4,673,568, 4,387,090 and 4,705,681. Automatic Dish Detergents are described in U.S. Pat. Nos. 6,020,294, 6,017,871, 5,968,881, 5,962,386, 5,939,373, 5,914,307, 5,902,781, 5,705,464, 5,703,034, 5,703,030, 5,679,630, 5,597,936, 5,581,005, 5,559,261, 4,515,705, 5,169,552, and 4,714,562.
All parts, percentages and proportions refer to herein and in the claims are by weight unless otherwise indicated.
The values and dimensions disclosed herein are not to be understood as being strictly limited to the exact numerical values recited. Instead, unless otherwise specified, each such value is intended to mean both the recited value and a functionally equivalent range surrounding that value. For example, a value disclosed as “50%” is intended to mean “about 50%.”
All publications cited herein are incorporated by reference in their entirety.
The following examples are provided as specific embodiments of the present invention.
JEFFAMINE ED900 polyetheramine (8.0 g/8.9 mmol) was combined with the fragrances listed in Table 1 (2 equiv total to JEFFAMINE) in a vial and the mixture was stirred neat at room temperature for 24 hours. The resulting products (10.4 g) were submitted for NMR analysis.
This analysis indicated that di-imine products were readily formed between the JEFFAMINE and fragrances. Therefore, such materials are of use in a fragrance accord as a delayed delivery system.
Imines and Michael adducts are known to hydrolyze slowly in the presence of dilute aqueous acid, which can be from a number of commonly occurring sources. In turn, this triggers the release of the sequestered fragrance ingredient, providing a longer period of fragrance performance.
Malodor acids, such as butyric and isovaleric, can be used as acidic triggers to cause the hydrolysis and release of the fragrance ingredient. The resulting free amine is able to sequester the malodor acid in an acid-base ion pair, reducing the concentration of malodor acid in the headspace (Scheme 3).
GC Headspace (HS) analysis of JEFFAMINE ED900 and the reactive polymer described in Ser. No. 14/731,865, versus model malodor compounds, isovaleric acid (IVA), n-butylamine (nBA), and pentanethiol (PT) versus a diethylphthalate control were compared (Table 2).
Aldehyde-rich accords of particular use in the fragrance delivery composition of this invention are listed in Table 3.
| Number | Date | Country | |
|---|---|---|---|
| 62279387 | Jan 2016 | US |
