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Encapsulation of bulky fragrance molecules

  • US 8,609,600 B2
  • Filed: 09/04/2007
  • Issued: 12/17/2013
  • Est. Priority Date: 09/04/2006
  • Status: Active Grant
First Claim
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1. A fragrance composition to be incorporated into the core of a core shell capsule, comprising:

  • I) 60-100% by weight of at least 5 different fragrance compounds, each of the at least 5 different fragrance compounds possessing any of the following structural features a) to g), andII) 0-40% by weight of other benefit agents which possess any of the following structural features a) to g), pro-fragrances, and solvents;

    a) a fragrance compound containing more than one ring, each ring having between 3 and 8 atoms of any of carbon, oxygen, nitrogen or sulfur in any ring and no atoms being shared by any of the rings, and selected from the group consisting of methyl n-{4-(4-hydroxy-4-methylpentyl)-3-cyclohexen-1-methylene}-anthranilate, endo 4-(5-methyl1-5-norbornen-2-yl)-pyridine, 2,5,5-trimethyl-2-phenyl1,3-dioxane, isocamphyl cyclohexanol, 2-(2,4-dimethyl-3-cyclohexyl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane, vanillin propylene glycol acetal, indol-hydroxycitronellal schiff s base, dimethyl-2-(5′

    ,5′

    ,8′

    ,8′

    -tetramethyl-5′

    ,6′

    ,7′

    ,8′

    -tetrahydro-naphthalen-2′

    -yl)1,3-dioxolane, 2 cyclohexylidene-2-phenylacetonitrile, benzyl cinnamate, benzyl eugenol, cinnamyl anthranilate, cinnamyl cinnamate, cinnamyl phenyl acetate, 4-methyl-2-phenyltetrahydro-2h-pyran, and dibenzyl ketone;

    b) a fragrance compound having at least two rings, each ring having between 3 and 8 atoms of any of carbon, oxygen, nitrogen or sulfur in which any rings share one common atom, and selected from the group consisting of 2-methyl-1,5-dioxaspiro[5.5]undecane, 2,2,3′

    ,7′

    ,7′

    -pentamethylspiro(1,3-dioxan-5,2′

    -norcarane), decahydro-spiro[furan-2(3h), 5′

    -(4,7-methano-5h-indene)], 3,3-dimethyl-1,5-dioxaspiro[5.5]undecane, 4-methyl-1-oxaspiro[5.5]undecene, and 8-methyl-1-oxaspiro[4.5]decan-2-one;

    c) a fragrance compound having at least two rings, each ring having between 3 and 8 atoms of any carbon, oxygen, nitrogen or sulfur in which any two rings share at least two adjacent common atoms, and selected from the group consisting of methyl naphthyl ketone, isobutylquinoline, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5h)-indanone, tricyclo decenyl acetate and its homologues tricyclo decenyl propionate and tricyclo decenyl isobutyrate, cedryl methyl ether, 4-(1,3-benzodioxol-5-yl)butan-2-one, 3a-ethyl dodecahydro-6,6,9a-trimethyl naphtho[2,1-b]-furan, 2,5,5-trimethyl-octahydronaphthalen-2-ol, α

    -cedrene, 8-cedren-13-ol, cedryl methyl ether, α

    -methyl-3,4-methylenedioxy hydrocinnamic aldehyde, ethyl tricyclo[5,2,1,0]decan-2-carboxylate, 1,4-cineole (470-67-7), 1,8-cineole, borneol, bornyl acetate, isoborneol, isobornyl acetate, isobornyl formate, isobornyl methyl ether, isobornyl propionate, 2-ethyl-5(or

         6)-methoxy bicyclo[2.2.1]heptane and 1-ethyl-3-methoxy tricyclo[2.2.1.02,6]heptane, 2-ethylidene-6-isopropoxy bicyclo[2.2.1]heptane, 5′

    (or 6′

    )-(methylnorborn-5′

    -en-2′

    -yl)-2-menthyl-1-en-3-ol, 2-[(1,7,7-trimethybicyclo[2,2,1]hept-2-yl)oxy]-ethanol, 7 acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethyl-naphthalene, patchouli alcohol, norpathoulenol, isobornyl cyclohexanol, 2,2,7,7-tetramethyltricyclo[6.2.1.01,6]undecane-5-one, octahydro-7,7,8,8-tetramethyl-2,3b-methano-3bh-cyclopenta(1,3)cyclopropa(1,2)benzene-4-methyl acetate, nootkatone, 9-ethylidene-3-oxatricyclo[6.2.1.02,7]undecane-4-one, cedryl methyl ether, α

    -pinene, β

    -pinene, 5,6,7,7a-tetrahydro-4,4,7a-trimethyl-2(4h)-benzofuranone (dihydroactinidolide), 1,3-dimethyl-8-(1-methylethyl)-tricyclo[4.4.0.0.02,7]dec-3-ene (α

    -copaene), camphene, 4 acetyl-6-tertiary-butyl-1,1-dimethyl indane, 5-acetyl-1,1,2,6-tetramethyl-3-isopropyl-dihydroinden, β

    -nephthyl isobutyl ether, decahydro-β

    -naphthyl acetate, 6-methoxydicyclopentadiene carboxaldehyde, 4-methyl tricyclo[6.2.1.0]undecan-5-one, 4,4a,5,8,8a-hexahydro-3′

    ,7′

    -dimethyl spiro(1,4-methanonaphthalene-2(1h), 2′

    -oxirane), dodecahydro-3a,6,6,9a-tetramethyl-naphto[2,1-b]furan, and 6-ethylidene octahydro-5,8-methano-2h-1-benzopyran-2-one;

    d) a fragrance compound containing a single alicyclic ring which contains at least 5 atoms, but no more than 8 atoms, of any of carbon, oxygen, nitrogen and sulfur in which at least one of the carbon atoms of the ring has two substituents, or a carbon atom alpha to the ring is a tertiary carbon atom, or the ring has substituents on at least three of the atoms which make up the ring, and selected from the group consisting of para-tertiary-butyl-cyclohexanol, ortho-tertiary-butyl-cyclohexanol, para-tertiary-butyl-cyclohexanone, γ

    -ionone, β

    -damascenone, 4 acetoxy-4-methyl-2-propyl-tetrahydro-2h-pyran, ortho tertiary amyl cyclohexanyl acetate, 2,4-dimethylcyclohexanemethanol, ethyl acetoacetate propylene glycol acetal, isocyclogeraniol, 5-methyl-3-butyltetrahydropyran-4-yl acetate, fenchol, (−

    )-2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, ethylacetoacetate ethyleneglycol ketal, nopol, nopyl acetate, 2,6,6-trimethyl-1-cyclohexen-1-acetoaldehyde, 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 2,4,6-trimethyl-3-cyclohexene-1-methanol, 3-methyl-5-propyl-2-cyclohexen-1-one, dynascone (firmenich), α

    -iso-methyl-ionone, 3,3-dimethyl-5-(2′

    ,2′

    ,3′

    -trimethyl-3′

    -cyclopenten-1′

    -yl)-4-penten-2-ol, 2,2-dimethyl-6-methylene cyclohexane carboxylic acid methyl ester, 5-pentyl-2,2,5-trimethylcyclopentanone, 2,2,6-trimethyl-α

    -propyl-cyclohexanepropanol, 2-tert-butyl cyclohexyl oxy-2-butanol, myrac aldehyde, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal, 2,2,5-trimethyl-5-pentylcyclopentanone, β

    -2,2,3-tetramethyl-3-cyclopentene-1-butanol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 3-methyl-5-(2,2,3-trimethyl cyclopent-3-en-1-yl-pentan-2-ol, 4-tert-pentylcyclohexanone, 4-(1-ethoxyvinyl)-3,3,5,5-tetramethyl cyclohexanone, ethyl 2-tert-butyl cyclohexyl carbonate, methyl 2-hexyl-3-oxocyclopentanecarboxylate, 3-oxo-2-(2-cis-pentenyl)cyclopentane acetic acid methyl ester, and 2-pentyl-3-methyl-2-cyclopenten-1-one;

    e) a fragrance compound containing at least one macrocyclic ring, which is a ring having more greater than eight atoms of any of carbon, nitrogen oxygen or sulfur in the ring, and selected from the group consisting of 3 methylcyclopentadecanone, 3-methylcyclopentadecenone, 3-methylcyclopentadecanol, cyclopentadecanone, (Z)-4-cyclopentadecen-1-one, trimethyl-oxabicyclotridecadiene, 15-pentadecenolide, 12-methyl-14-tetradec-9-enolide, oxacycloheptadec-7(or

         10)-en-2-one, [3 (or

         4)-cycloocten-1-yl]methyl carbonate, methyl 2,6,10-trimethylcyclododeca-2,5,9-trien-1-yl ketone, cyclodecyl methyl ether, and ethoxyymethoxycyclidodecane;

    f) a fragrance compound containing at least one substituted aromatic ring containing at least 5 atoms of any of carbon, oxygen, nitrogen or sulfur, but in which at least one substituents has a tertiary carbon in a position alpha or beta to the ring, and selected from the group consisting of 2-methyl-3-(4-tert-butylphenyl)propanal, 2,5,5-trimethyl-2-phenyl-1,3-dioxane, 4-tert-butylbenzennpropionaldehyde, dimethybenzylcarbinyl acetate, and 5-phenyl-5-methyl-3-hexanone; and

    g) a fragrance compound containing a substituted aromatic ring comprising at least 5 atoms with at least 3 substituents groups on the ring all of which must contain at least 2 atoms from among carbon, oxygen, nitrogen or sulfur, and selected from the group consisting of 1,3,5-trimethoxybenzene, acetyl eugenol, acetyl vanillin, musk thibetone, musk ambrette, 3,4-dimethoxybenzoic acid, 3,4-methylenedioxybenzyl acetate and veratraldehyde,wherein 40-100% by weight of the at least 5 different fragrance compounds comprise at least 3 bulky molecules having a molecular weight of less than 325 atomic mass units and a C log P value between C log P 1.00 and C log P 4.00,wherein the fragrance composition comprises less than 1% by weight of a fragrance aldehyde, andwherein the other benefit agents are not constrained by the molecular weight restrictions.

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