ES2607280T3 - Composiciones que contrarrestan el mal olor (MOC) - Google Patents

Composiciones que contrarrestan el mal olor (MOC) Download PDF

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ES2607280T3
ES2607280T3 ES11804991.5T ES11804991T ES2607280T3 ES 2607280 T3 ES2607280 T3 ES 2607280T3 ES 11804991 T ES11804991 T ES 11804991T ES 2607280 T3 ES2607280 T3 ES 2607280T3
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methyl
ethyl
group
dec
penten
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John Martin Behan
Keith Douglas Perring
Alan Forbes Provan
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Givaudan SA
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Givaudan SA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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    • A61K8/37—Esters of carboxylic acids
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    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
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    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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    • C11B9/0007—Aliphatic compounds
    • C11B9/0023—Aliphatic compounds containing nitrogen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
    • C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
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    • C11B9/0057—Spiro compounds
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
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    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11B9/00—Essential oils; Perfumes
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11B9/00—Essential oils; Perfumes
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0084—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing more than six atoms
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    • C11B9/0069—Heterocyclic compounds
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Abstract

Composición MOC, en particular una composición desodorante, que comprende, como mínimo, el 25% p/p en total, como mínimo, de 3 compuestos extraídos del grupo A y el grupo B siguientes: A. como mínimo, el 5% en total, como mínimo, de uno de los compuestos siguientes: 2-ciclohexiliden-2- fenilacetonitrilo, 2-acetil-1,2,3,4,5,6,7,8-octahidro-1,2,8,8-tetrametilnaftaleno, ciclohexiliden(2- metilfenil)acetonitrilo, (E)-3-(2-hidroxifenil)acrilato de 2-etoxi-4-formilfenilo y 3-(2-hidroxifenil)acrilato de (E)- dec-9-enilo, B. opcionalmente, como mínimo uno de los compuestos siguientes: 3,8,8,11a-tetrametildodecahidro-5H-3,5a- epoxi-naft[2,1-C]oxepin, oxacicloheptadec-10-en-2-ona, 3-metil-5-(2,2,3-trimetil-3-ciclopenten-1-il)-4- penten-2-ol, 2,6,6-trimetil-1,3-ciclohexadien-1-carboxilato de etilo, 2-metil-3-(4-metoxifenil)propanal, 3-(3- isopropilfenil)butanal, 2(6)-metil-8-(1-metiletil)biciclo[2,2.2]oct-5-en-2(3)-il-1,3-dioxolano, 1-metil-2-(1,2,2- trimetilbiciclo[3,1.0]-hex-3-ilmetil)ciclopropil)metanol, 3,7-dimetil-2(3),6-nonadienonitrilo, 2-(2-(4-metil-3- ciclohexen-1-il)propil)ciclopentanona, 2-ciclohexil-1,6-heptadien-3-ona, (2Z)-2-etil-4-(2,2,3-trimetilciclopent- 3-en-1-il)but-2-en-1-ol, ciclopropanocarboxilato de 2-{[1-(3,3-dimetilciclohexil)etil]oxi}-2-metilpropilo, 1- espiro[4,5]dec-7-en-7-il-4-penten-1-ona, 1-espiro[4,5]dec-6-en-7-il-4-penten-1-ona, 1- (trimetilciclododecatrienil)-etanona, carbonato de 4-cicloocten-1-il metilo, 2-(2,4-dimetilciclohexil)-piridina, en los que el cálculo del porcentaje en peso de cada componente se ha realizado en base a que se ha ignorado la presencia de un diluyente.

Description

imagen1
imagen2
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Las composiciones y propiedades MOC observadas (según lo determinado en la prueba de reducción del olor) de diversas mezclas se muestran en la tabla 2 (a), (b) y (c). En todos los casos la muestra llamada M00 representa un control que comprende solo el disolvente dipropilenglicol.
Las tablas 2(a) y (b) detallan composiciones de acuerdo con la presente invención. La tabla 2(c) detalla de las composiciones que no cumplen los requisitos de la presente invención.
Clave para las tablas 2(a), (b) y (c)
DPG: Dipropilenglicol
S: Disolvente
MIV Valor medio inhibición
de
*: Media de 8 experimentos
Tabla 2A – Composiciones y eficacias desodorantes de las composiciones de la presente invención
Grupo al que pertenecen
MUESTRAS
Compuesto
A y B A M00 M61 M41 M60 M23 M14
Oxacicloheptadec–10–en–2–ona (Ambrettolide)
Y 0 0 0 0 2 0 0
3–metil–5–ciclotetradecenona (Cosmone)
0 0 0 0 1 0 0 0
3–Metil–5–(2,2,3–trimetil–3–ciclopenten–1–il)–4– penten–2–ol (Ebanol)
Y 0 0 0 0 1 0 0
2,6,6–trimetil–1,3–ciclohexadien–1–carboxilato de etilo ona (safranato de etilo)
Y 0 0 0 0 0 1 0
2–Metil–3–(4–metoxifenil)propanal ona (Fennaldehído)
Y 0 0 0 0 0 0 4
3–(4–etilfenil)–2,2–dimetilpropanonitrilo (Fleuranil)
0 0 0 0 8 0 0 0
3–(3–isopropilfenil)butanal ona (Florhydral)
Y 0 0 0 0 4 0 0
1–(3,3–dimetilciclohex–1–en–1–il)pent–4–en–1– ona (Galbanone)
0 0 0 0 0 0 0,1 0
2–acetil–1,2,3,4,5,6,7,8–octahidro–1,2,8,8– tetrametilnaftaleno (Georgywood)
Y Y 0 8 8 8 8 8
2–etil–6,6–dimetilciclohex–2–en–1–carboxilato de etilo (Givescone)
0 0 0 0 0 0 1 0
2(6)–Metil–8–(1–metiletil) biciclo [2,2.2] oct–5– en–2(3)–il–1, 3–dioxolano ona (Glycolierral)
Y 0 0 1 0 0 0 0
1–metil–2–{[(1,2,2–trimetilbiciclo[3,1.0]hex–3– il]metil}ciclopropil)metanol (Javanol)
Y 0 0 0 0 0 0 1
2,5,5–trimetil–6,6–bis(metiloxi)hex–2–eno (Metilo pomelo)
0 0 0 1 0 0 0 1
1,4–dioxaciclohexadecano–5,16–diona (almizcle MC4)
0 0 0 0 0 0 0 8
2,4–dimetil–2–(5,5,8,8–tetrametil–5,6,7,8– tetrahidronaftalen–2–il)–1,3–dioxolano (Okoumal)
0 0 0 1 0 0 1 0
2–Ciclohexiliden–2–fenilacetonitrilo (Peonile)
Y Y 0 0 8 0 0 0
Pharaone
Y 0 0 0 0 0 0,1 0
Ciclopropanocarboxilato de 2–{[1–(3,3– dimetilciclohexil)etil] oxi}–2–metilpropilo (Serenolide)
Y 0 0 0 0 0 0 8
Silvanone®
0 0 0 0 0 16 0 0
5–metilheptan–3–ona oxima (Stemone)
0 0 0 0 1 0 0 0
3–(2–hidroxifenil)acrilato de (E)–dec–9–enilo (Tonkarose)
Y Y 0 1,6 0 0 0 0
1–ciclopropilmetil–4–metoxi–benceno (Toscanol)
0 0 0 0 0 1 0 0
Ciclohexadec–5–enona (Velvione)
0 0 0 2 0 0 0 0
4–cicloocten–1–ilmetilo (Violiff)
Y 0 0 0 1 0 0 0
DPG
S S 100 85,4 73 68 88,8 70
% total
100 100 100 100 100 100
Análisis por grupo:
M00 M61 M41 M60 M23 M14
% de compuestos de fragancia en la composición total (incl. diluyente)
0 14,6 27 32 10,2 30
No. de compuestos del grupo A y B
0 3 3 4 3 4
% de compuestos del grupo A y B en total
0 10,6 17 15 9,1 21
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Tabla 2(c) – Composiciones y eficacias desodorantes de las composiciones de la presente invención
Grupo al que pertenecen
MUESTRAS (comparativas)
Compuestos
A y B A M00 C27 C44 C48 C11 C16
Octahidro–2H–cromen–2–ona (biciclononalactona)
0 0 0 0 1 0 0 0
Dihidro–beta–ionona
0 0 0 0 0 4 0 0
2,6–dimetiloct–7–en–2–ol
0 0 0 16 0 16 16 0
(4E)–3–metil–5–(2,2,3–trimetilciclopenten–3–en–1– il)pent–4–en–2–ol (Ebanol)
Y 0 0 0 1 0 0 0
3–(3–isopropilfenil)butanal ona (Florhydral)
Y 0 0 0 0 0 4 0
1–[(3Z)–ciclooct–3–en–1–il]propan–1–ol (Florymoss)
0 0 0 0 1 0 0 0
2–(1–metilpropil)ciclohexanona (Freskomenthe)
0 0 0 0 1 0 0 1
1–(3,3–dimetilciclohex–1–en–1–il)pent–4–en–1–ona (Galbanone)
0 0 0 0 0,1 0 0 0
2–etil–6,6–dimetilciclohex–2–en–1–carboxilato de etilo (Givescone)
0 0 0 0 0 1 1 0
Propanoato de 2–{[1–(3,3–dimetilciclohexil)etil] oxi}–2– metilpropilo (Helvetolide)
0 0 0 0 0 0 0 4
1–metil–2–{[(1,2,2–trimetilbiciclo[3,1.0]hex–3– il]metil}ciclopropil)metanol (Javanol)
Y 0 0 1 0 0 0 0
2,4,4,7–tetrametilnona–6,8–dien–3–ona oxima (Labienoxime)
0 0 0 0,01 0 0 0,01 0
1,4–dioxaciclohexadecano–5,16–diona (almizcle MC4)
0 0 0 0 0 0 0 8
2–Ciclohexiliden–2–fenilacetonitrilo (Peonile)
Y Y 0 0 0 0 0 8
2–etil–4–(2,2,3–trimetilciclopent–3–en–1–il)but–2–en– 1–ol (Radjanol
Y 0 0 0 0 0 4 4
Super)
Silvanone®
0 0 0 16 0 0 0 0
5–metilheptan–3–ona oxima (Stemone)
0 0 0 0 0 0 1 0
3–(2–hidroxifenil)acrilato de (E)–dec–9–enilo (Tonkarose)
Y Y 0 1,6 1,6 1,6 0 0
1–ciclopropilmetil–4–metoxi–benceno (Toscanol)
0 0 0 0 0 1 0 1
undeca–1,3,5–trieno (Undecatrieno)
0 0 0 0 0 1 0 0
2–(2,4–dimetilciclohexil)–piridina (Zinarine)
Y 0 0 2 0 0 0 0
DPG
S S 100 63,39 94,3 75,4 73,99 74
% total
100 100 100 100 100 100
Análisis por grupo
M00 C27 C44 C48 C11 C16
% de compuestos de fragancia en la composición total (incl. diluyente)
0 36,61 5,7 24,6 26,01 26
No. de compuestos del grupo A y B
0 3 2 1 2 2
% de compuestos de fragancia del grupo A y B en la composición total (incl. diluyente)
0 4,6 2,6 1,6 8 12
% de componente de fragancia de compuestos de grupo A y B (ignorado el diluyente)
0 12,56 45,61 6,50 30,76 46,15
No. de compuestos del grupo A
0 1 1 1 0 1
% de compuestos de fragancia del grupo A en la composición total (incl. diluyente)
0 1,6 1,6 1,6 0 8
% de componente de fragancia de compuestos de grupo A (ignorado el diluyente)
0 4,37 28,07 6,50 0 30,77
Eficacia desodorante:
Puntuación DTS
2,01* 1,64 1,68 1,76 1,81 1,87
MIV (DPG=2,01)
0 0,18 0,16 0,12 0,07 0,07
Las composiciones de acuerdo con la presente invención detalladas en las tablas 2(a) y (b) muestran una buena desodorante (por ejemplo, MIV> 0,25 en la prueba de la reducción del olor), mientras que las composiciones que no
5 cumplen los requisitos de la presente invención detalladas en la tabla 2(c) muestran un rendimiento desodorante deficiente. Las composiciones que contienen aproximadamente el 10% de dos compuestos del Grupo A muestran particularmente una buena capacidad desodorante (MIV> 0,4).
10 Ejemplo 2
En la tabla 3 se detallan composiciones de ejemplo de acuerdo con la presente invención que son más complejas que los ejemplos anteriores y más adecuadas para satisfacer las necesidades hedónicas de productos, tales como productos desodorantes y antitranspirantes.
Tabla 3
Grupo al que pertenecen
MUESTRAS (comparativas) % (p/p)
Compuesto
A B CPD/1/0 9 CPD/2/0 9 CPD/3/0 9
2–Feniletanol
0 0 30 10 7,5
Oxacicloheptadec–10–en–2–ona (Ambrettolide)
0 1 0,5
Acetato de bencilo
0 0 5
DPG
S S 30 32,4 41,56
3–Metil–5–(2,2,3–trimetil–3–ciclopenten–1–il)–4–penten– 2–ol (componente principal del Ebanol)
0 1 3
2,6,6–trimetil–1,3–ciclohexadien–1–carboxilato de etilo ona (safranato de etilo)
0 1 0,5
2–Metil–3–(4–metoxifenil)propanal ona (Fennaldehído)
0 1 2
3–(3–isopropilfenil)butanal ona (Florhydral)
0 1 4
2–acetil–1,2,3,4,5,6,7,8–octahidro–1,2,8,8– tetrametilnaftaleno (Georgywood)
1 0 2 2
Acetato de geranilo
0 0 5 5
Aldehído hexilcinnámico
0 0 7 5 6
Acetato de 3–pentiltetrahidro–2H–piran–4–ilo (Jasmopyrane Forte)
0 0 1
3,7–dimetilnona–2,6–dienenitrilo (Lemonile)
0 1 2 5
Linalol
0 0 6,3 12
2–[2–(4–metilciclohex–3–en–1–il)propil]ciclopentanona (Nectaryl)
0 1 1
Nerol
0 0 3 5
Terpenos de naranja
0 0 9 10
2–Ciclohexiliden–2–fenilacetonitrilo (Peonile)
1 0 3 9 12
2–Ciclohexilhepta–1,6–dien–3–ona (Pharaone) 10% en diluyente
0 1 0,2
2–etil–4–(2,2,3–trimetilciclopent–3–en–1–il)but–2–en–1– ol (Radjanol Super)
0 1 1 4
Ciclopropanocarboxilato de 2–{[1–(3,3– dimetilciclohexil)etil] oxi}–2–metilpropilo (Serenolide)
0 1 10 4
1–espiro[4,5]dec–7–en–7–il–4–penten–1–ona y 1– espiro[4,5]dec–6–en–7–il–4–penten–1–ona (ambos componentes de la espirogalbanona) Espirogalbanona al 10% en diluyente
0 1 0,2
3–(2–hidroxifenil)acrilato de (E)–dec–9–enilo (Tonkarose)
1 0 1,6 1,04
Undecalactona
0 0 1
2–(2,4–dimetilciclohexil)–piridina (Zinarine)
0 1 0,2
Total %
100 100 100
% total de disolvente
30,18 32,4 41,74
No. de compuestos del grupo A
2 3 2
Suma del % de los compuestos del grupo A
5 12,6 13,04
No. de compuestos del grupo B
7 2 6
Suma del % de los compuestos del grupo B
17,52. 9 10,72.
Suma de los grupos A y B
22,52. 21,6 23,76
Suma de los grupos A y B (ady. solv.) %
32,25 31,95 40,78

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