WO2023083445A1 - Compositions comprising trpm8 agonistic cooling agents - Google Patents

Compositions comprising trpm8 agonistic cooling agents Download PDF

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Publication number
WO2023083445A1
WO2023083445A1 PCT/EP2021/081229 EP2021081229W WO2023083445A1 WO 2023083445 A1 WO2023083445 A1 WO 2023083445A1 EP 2021081229 W EP2021081229 W EP 2021081229W WO 2023083445 A1 WO2023083445 A1 WO 2023083445A1
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Prior art keywords
rac
isoxazole
alkyl
methyl
peg
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PCT/EP2021/081229
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French (fr)
Inventor
Benoit JOIN
Sebastian AHLES
Sven Siegel
Arnold Machinek
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Symrise Ag
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Priority to PCT/EP2021/081229 priority Critical patent/WO2023083445A1/en
Publication of WO2023083445A1 publication Critical patent/WO2023083445A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention refers to the area of preservation and concerns new com- position comprising specific multi-purpose mixtures with anti-microbial activity, flavor boosting activity, flavor masking activity and soothing activity.
  • Cosmetic products are generally manufactured under sterile conditions to pre- vent contamination. In the case of foodstuffs, the requirements are even more strin- gent; dairy products, for example, must be subjected to high-temperature heating (“pasteurization”) before they can be marketed at all.
  • preservatives are added to cosmetics and food products.
  • preservatives are generally considered to be hazardous for contact with human skin and especially mucous membranes, because a chemical that is capable of killing mi- croorganisms is always suspected of triggering harmful processes in the human or- ganism.
  • the list of approved preservatives is therefore shrinking from year to year at the same rate as critical studies are revealing dangers for previously common sub- stances.
  • a first concept is to use synergistic mixtures of different preservatives.
  • Another approach pursues the possibility of identifying multifunctional substances or mixtures of substances that, in Addition to their primary properties, are also antimicrobially active, at least to a small extent. To the extent that these sub- stances contribute to the antimicrobial properties of a formulation, the amount of actual preservative can be reduced.
  • Benzisoxazoles are known molecules which are used as psychopharmaca for fighting various diseases.
  • US 5,668,154 A refers to novel pyridiniminyl-1 ,2-ben- sioxazoles and -benzisothiazoles, intermediates and processes for the preparation thereof, and methods of relieving memory dysfunction and treating depression.
  • US 5,114,936 A discloses 6,7-dihydro-3-phenyl-1 ,2-benzisoxazol-4(5H)- ones and -ols as as antipsychotic and analgesic agents
  • US 5,055,476 A suggest 3-(1 ,2-Benzisoxazol-3-yl)-4-pyridinamines and derivatives as an- algesics, for alleviating various memory dysfunctions characterized by a decreased cholinergic function, as cognition enhancers in the treatment of senile dementia such as Alzheimer's disease and as topical antiinflammatory agents for the treatment of var- ious dermatoses.
  • ES 2006887 A and ES 2006888 A (JANSSEN) refer to 3-Piperidinyl 1 ,2-benzo- isoxazoles and relate to their anti-psychotic and anti-serotonin activity
  • JP 9 268 188 A2 (MEIJI) relates to 1 -benzoyl-3[2-[4-(6-fluoro-1 ,2- benzoisoxa- zol-3-yl)-1 -piperidinyl]ethyl]perhydrobenzoimidazol-2-one ⁇ which is useful as a psy- chotropic agent such as an antischizophrenic, an antianxiety agent, or an antidepres- sant.
  • psy- chotropic agent such as an antischizophrenic, an antianxiety agent, or an antidepres- sant.
  • US 2005 026922 AA and US 2007 270430 AA concern ami- nomethylpyridyloxymethyl/benzisoxazole substituted azabicyclic compounds, a phar- maceutical composition comprising same, and a method of treating a cognitive disor- der selected from the group consisting of Asperger's disorder, Autistic Disorder, Oppo- sitional Defiant Disorder, and Conduct Disorder.
  • WO 2021 102896 A1 and WO 2021 105261 A1 disclose benzo- isoxazole derivatives and a method for modulating TRPV receptors by bringing them into contact with said derivatives.
  • compositions which are commonly used in cosmetic products or foodstuffs and which Additionally possess appreciable antimicrobial properties, so that their use can reduce the amount of preservative otherwise required for antimicrobial finishing , mask unpleasant flavors, particularly unpleasant flavors of fluorine derivatives and bitter compounds; and/or en- hance and/or boost the performance of a flavor, a physiological cooling/warming agent, a sweetener or a soothing agent.
  • a first object of the present invention refers to a composition comprising or con- sisting of
  • halogen including Br, Cl, and F
  • halogen including Br, Cl, and F
  • C 1 -C 6 alkyl C 1 -C 6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F)
  • C 1 -C 6 alkyloxy C 1 -C 6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F)
  • C 3 -C 7 cycloalkyl
  • -C (O) O- R 10 wherein R 10 is selected from hydrogen and C 1 -C 3 alkyl, and - SR 11 wherein R 11 is selected from hydrogen and C 1 -C 3 alkyl (including ethyl and isopropyl), and - C 5 -C 10 mono-or bicyclic aryl wherein 1 or 2 C-atoms are replaced by a het- ero atom independently selected from sulfur, nitrogen, and oxygen, option-
  • substituents selected from the group consisting of halogen (including Br, Cl, and F), C N, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C 1 - C 6 alkyloxy, C 1 -C 6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C 3 -C 7 cycloalkyl, -C(O)O-R 10 wherein R 10 is selected from hydrogen and C 1 -C 6 alkyl, and -SR 11 wherein R 11 is selected from hydro- gen and C 1 -C 3 alkyl (including ethyl and isopropyl); - R 2 , R 4 , R 5 , and R 7 are independently selected from hydrogen and C 1 -C 6 al- kyl; - R 6 is selected from hydrogen, C 1 -C 6 alkyl (e.g.
  • compositions according to the present invention in- clude compound (a) and one additional additive, namely compound (b), compound (c) or compound (d).
  • compound (b), compound (c) or compound (d) it is also possible having compositions with three or four components.
  • the preferred ratios by weight (b):(c), (b):(d) or (c):(d) are from about 10:90 to about 90:10 and preferably from about 25:75 to about 75:25.
  • preferred ratios by weight (b):(c):(d) are from about 30:30:40 to about 40:30:30.
  • Benzoisoxazole derivatives forming group (a) belong to the group of TRMP8 modulators.
  • the structures and their synthesis are known from WO 2021 102896 A1 and WO 2021 105261 A1 which are hereby incorporated by reference.
  • Non-limiting examples are compounds of formula (I), a salt or solvate thereof, wherein X is CR 3 wherein R 3 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 7 alkyl sub- stituted with one or two OH groups, C 3 -C cycloalkyl, C 3 -C 7 cycloalkyl substituted with one or two OH groups, C 5 -C 7 cycloalkenyl, C 5 -C ycloalkenyl substituted with one, two or three C 1 -C 3 alkyl groups, and phenyl; and the dotted line represents a single bond or a double bond;
  • X is CR 3 wherein R 3 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 7 al- kyl substituted with one or two OH groups, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl substi- tuted with one or two OH groups, C 5 -C 7 cycloalkenyl, C 5 -C 7 cycloalkenyl substituted with one, two or three C 1 -C 3 alkyl groups, and phenyl; and the dotted line represents a single bond; and n is 0.
  • Non-limiting examples are compound of formula (I), a salt or solvate thereof, wherein X is NR 3 , wherein R 3 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 7 al- kyl substituted with one or two OH groups, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl substi- tuted with one or two OH groups, C 5 -C 7 cycloalkenyl, C 5 -C 7 cycloalkenyl substituted with one, two or three C 1 -C 3 alkyl groups, and phenyl; and the dotted line represents a single bond or a double bond;
  • Non-limiting examples are compound of formula (I), a salt or solvate thereof, wherein X is NR 3 , wherein R 3 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 7 al- kyl substituted with one or two OH groups, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl substi- tuted with one or two OH groups, C 5 -C 7 cycloalkenyl, C 5 -C 7 cycloalkenyl substituted with one, two or three C 1 -C 3 alkyl groups, and phenyl; the dotted line represents a single bond; and n is 0.
  • Non-limiting examples are compound of formula (I), a salt or solvate thereof, wherein X is CR 3 , wherein R 3 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 7 al- kyl substituted with one or two OH groups, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl substi- tuted with one or two OH groups, C 5 -C 7 cycloalkenyl, C 5 -C cycloalkenyl substituted with one, two or three C 1 -C 3 alkyl groups, and phenyl; and the dotted line represents a single bond; n is 0; and R 1 is phenyl optionally substituted with up to five (e.g.
  • halogen including Br, Cl, and F
  • C 1 -C 6 alkyl C 1 -C 6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F)
  • C 1 -C 6 alkyloxy C 1 -C 6 alkyloxy comprising up to 5 halogen atoms (in- cluding Br, Cl, and F)
  • C 3 -C 7 cycloalkyl
  • -C(O)O-R 10 wherein R 10 is selected from hy- drogen and C 1 -C 3 alkyl
  • -SR 11 wherein R 11 is selected from hydrogen and C1- C3 alkyl (including ethyl and isopropyl).
  • non-limiting examples are compounds of formula (la), a salt or solvate thereof, wherein - X is selected C and N; - R 3 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 7 alkyl substituted with one or two OH groups, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl substituted with one or two OH groups, C 5 -C 7 cycloalkenyl, C 5 -C 7 cycloalkenyl substituted with one, two or three C 1 -C 3 alkyl groups, and phenyl; - R 1 is selected from hydrogen, - C 1 -C 6 alkyl, - C 1 -C 7 alkyl substituted with one or two OH groups, - C 3 -C 7 alkenyl, - phenyl optionally substituted with up to five (e.g.
  • halogen including Br, Cl, and F
  • - R 8 and R 9 are independently selected from hydrogen, and C 1 -C 6 alkyl, or - R 8 and R 9 form together with the C-atom to which they are attached a 3, 4, 5, 6, or 7-membered cycloalkyl ring.
  • Non-limiting examples are compounds of formula (la), a salt or solvate thereof, wherein X is C; and R 3 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 7 alkyl sub- stituted with one or two OH groups, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl substituted with one or two OH groups, C 5 -C 7 cycloalkenyl, C 5 -C 7 cycloalkenyl substituted with one, two or three C 1 -C 3 alkyl groups, and phenyl.
  • Non-limiting examples are compound of formula (la), a salt or solvate thereof, wherein X is C; - R 1 is selected from hydrogen, - C 1 -C 6 alkyl, - C 1 -C 7 alkyl substituted with one or two OH groups, - C 3 -C 7 alkenyl, - phenyl optionally substituted with up to five (e.g.
  • halogen including Br, Cl, and F
  • C 1 -C 6 alkyl C 1 -C 6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F)
  • C 1 -C 6 alkyloxy C 1 -C 6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F)
  • C 3 -C 7 cycloalkyl
  • -C(O)O-R 10 wherein R 10 is selected from hydro- gen and C 1 -C 3 alkyl, and -SR 11 wherein R 11 is selected from hydrogen and C1- C3 alkyl (including ethyl and isopropyl), - naphtyl optionally substituted with up to five (e.g.
  • halogen including Br, Cl, and F
  • substituents selected from the group consisting of halogen (including Br, Cl, and F), C N, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 alkyl compris- ing up to 5 halogen atoms (including Br, Cl, and F), C 1 -C 6 alkyloxy, C 1 -C 6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C 3 -C 7 cycloalkyl, - C(O)O-R 10 wherein R 10 is selected from hydrogen and C 1 -C 3 alkyl, and - SR 11 wherein R 11 is selected from hydrogen and C 1 -C 3 alkyl (including ethyl and isopropyl); - R 2 , R 4 , and R 5 are independently selected from hydrogen and C 1 -C 6 alkyl; - R 3 is hydrogen; - R 6 is selected from hydrogen, C 1 -C 6 alkyl (e.g.
  • - R 7 is hydrogen
  • - R 8 and R 9 are independently selected from hydrogen, and C 1 -C 6 alkyl, or - R 8 and R 9 form together with the C-atom to which they are attached a 3, 4, 5, 6, or 7-membered cycloalkyl ring.
  • the compounds of formula (la) wherein X is C are compound of formula (lb) have the relative stereochemistry as depicted wherein - R 1 is selected from hydrogen, - C 1 -C 6 alkyl, - C 1 -C 7 alkyl substituted with one or two OH groups, - C 3 -C 7 alkenyl, - phenyl optionally substituted with up to five (e.g.
  • halogen including Br, Cl, and F
  • C 1 -C 6 alkyl C 1 -C 6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F)
  • C 1 -C 6 alkyloxy C 1 -C 6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F)
  • C 3 -C 7 cycloalkyl
  • -C(O)O-R 10 wherein R 10 is selected from hydro- gen and C 1 -C 3 alkyl, and -SR 11 wherein R 11 is selected from hydrogen and C 1 - C 3 alkyl (including ethyl and isopropyl), - naphtyl optionally substituted with up to five (e.g.
  • halogen including Br, Cl, and F
  • C 1 -C 6 alkyl C 1 -C 6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F)
  • C 1 -C 6 alkyloxy C 1 -C 6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F)
  • C 3 -C 7 cycloalkyl
  • -C(O)O-R 10 wherein R 10 is selected from hydro- gen and C 1-C 3 alkyl, and -SR 11 wherein R 11 is selected from hydrogen and C 1 - C 3 alkyl (including ethyl and isopropyl), and - C 5 -C 10 mono-or bicyclic aryl wherein 1 or 2 C-atoms are replaced by a hetero atom independently selected from sulfur, nitrogen, and oxygen, optionally substi- tuted with up to three (e
  • substituents selected from the group consisting of halogen (including Br, Cl, and F), C N, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 alkyl compris- ing up to 5 halogen atoms (including Br, Cl, and F), C 1 -C 6 alkyloxy, C 1 -C 6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C 3 -C 7 cycloalkyl, - C(O)O-R 10 wherein R 10 is selected from hydrogen and C 1 -C 3 alkyl, and - SR 11 wherein R 11 is selected from hydrogen and C 1 -C 3 alkyl (including ethyl and isopropyl); - R 3 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 7 alkyl substituted with one or two OH groups, C 3 -C 7 cycloalkyl, C 3 -C 7 cyclo
  • - R 8 and R 9 are independently selected from hydrogen, and C 1 -C 6 alkyl, or - R 8 and R 9 form together with the C-atom to which they are attached a 3, 4, 5, 6, or 7-membered cycloalkyl ring.
  • R 1 is selected from C 1 -C 6 alkyl, C 1 -C 7 alkyl substituted with one or two OH groups, and C 3 -C 7 alkenyl.
  • R 1 is selected from C 1 -C 6 alkyl, C 1 -C 7 alkyl substituted with one or two OH groups, and C 3 -C 7 alkenyl;
  • R 2 is hydrogen or methyl; and
  • R 8 and R 9 are methyl.
  • R 1 is selected from C 1 -C 6 alkyl, C 1 -C 7 alkyl substituted with one or two OH groups, and C 3 -C 7 alkenyl
  • R 2 is hydrogen or methyl
  • R 4 is hydrogen
  • R 5 is C 1 -C 3 alkyl
  • R 8 and R 9 are methyl.
  • R 1 is selected from C 1 -C 6 alkyl, C 1 -C 7 alkyl substituted with one or two OH groups, and C 3 -C 7 alkenyl;
  • R is hydrogen or methyl;
  • R 4 is hydrogen,
  • R 5 is C 1 - 3 alkyl;
  • R 6 is methyl or isopropyl; and
  • R 8 and R 9 are methyl.
  • the prefix "rac” refers to the relative stereochemistry of the respective descriptors (R, S) disclosing the racemic mixture of both enantiomers; the prefix “rel” refers to the relative stereochemistry of the respective descriptors (R, S) referring to a single, unassigned enantiomer.
  • Chemical names with no stereochem- ical descriptor i.e. neither R nor S refer to mixtures of diastereomers and enantiomers.
  • alkyl refers to linear or branched alkyl
  • alkenyl refers to linear or branched alkyl comprising at least one car- bon-to-carbon double bond, e.g. 2 or 3 double bonds
  • cycloalkenyl refers to cy- cloalkyl comprising at least one carbon-to-carbon double bond with the proviso that the ring is not saturated.
  • the compounds as defined by formula (I) (which encompass the compounds of formula (la) and (lb)) comprise several chiral centers and as such may exist as a mix- ture of stereoisomers, or they may be resolved as isomerically pure forms.
  • Resolving stereoisomers Ads to the complexity of manufacture and purification of these com- pounds and so it is preferred to use the compounds as mixtures of their stereoisomers simply for economic reasons. However, if it is desired to prepare individual stereoiso- mers, this may be achieved according to methods known in the art, e.g. preparative HPLC and GC, crystallization or stereoselective synthesis. Accordingly, the chemical structures depicted herein encompass all possible stereoisomers forms of the illus- trated compounds.
  • the compounds as defined by formula (I) may exist in unsolvated forms as well as solv- ated forms, including hydrated forms and as N-oxides. In general, compounds may be hydrated, solvated or N-oxides. Certain compounds may exist in multiple crystalline or amorphous forms. In general, all physical forms are equivalent for the uses contem- plated herein and are intended to be within the scope of the present invention.
  • solute means a compound formed by solvation (the combination of solvent molecules with molecules or ions of the solute), or an aggregate that consists of a solute ion or molecule, i.e., a compound as defined by formula (I) (which encompass the compounds of formula (la) and (lb)), with one or more solvent molecules.
  • formula (I) which encompass the compounds of formula (la) and (lb)
  • solvents can be but are not limited to: acetone, acetonitrile, benzene, cyclohexane, dihy- drolevoglucosenone, methyl-tetrahydrofuran, pentylene glycol, ethylene glycol, petro- leum ether, ethyl lactate, methyl lactate, propyl lactate, diethylether, tert-butyl methyl ether, dimethylsulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, dioxane, ethanol, ethyl acetate, ethylene glycol, diethylene glycol, propylene glycol, heptane, hexane, methanol, toluene and xylene.
  • Salt refers to a salt of a compound as defined by formula (I) (which encompass the compounds of formula (la) and (lb)), which possesses the desired pharmacological activity of the parent compound.
  • Such salts include: (1 ) acid Addition salts, formed with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like; or formed with organic acids such as amino acids, acetic acid, trifluoroacetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3- (4-hydroxybenzoyl) benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1 , 2-
  • Physiological cooling agents forming group (b1 ) are chemical substances initi- ating a cooling effect when brought into contact with human skin or mucosa.
  • these agents represent menthol or menthol compounds are preferably selected from the group formed by the species depicted in the following table (including their optical isomers and racemates):
  • a first important representative of the substances forming component (b) is mono-menthyl succinate, which as a substance was patented as early as 1963 by
  • the former structure is obtained by esterification of lactic acid with menthol, the latter by acetylation of menthone with glycerol (cf. DE 2608226 A1 , H&R).
  • This group of compounds also includes 3-(l-menthoxy)-1 ,2, propanediol, also known as Cooling Agent 10 (US 6,328,982, TIC), and 3-(l-menthoxy)-2-methyl-1 ,2, propanediol, which has an Additional methyl group.
  • 3-(l-menthoxy)-1 ,2, propanediol is prepared starting from menthol according to the following scheme (see US 4,459,425, Takasago):
  • menthol compounds were developed for the first time which have a C-C bond in the 3-position and of which a number of representatives can also be used in the sense of the invention. These substances are generally referred to as WS types.
  • the basic body is a menthol derivative in which the hydroxyl group is replaced by a carboxyl group (WS-1 ). All other WS types are derived from this structure, such as the species WS-3, WS-4, WS-5, WS-12, WS-14 and WS-30, which are also pre- ferred in the sense of the invention.
  • the following two diagrams show the synthesis routes:
  • esters derived from WS-1 are described, for example, in US 4,157,384, and the corresponding N-substituted amides in J. Soc. Cosmet. Chem. pp. 185-200 (1978).
  • Physiological cooling agents which are particularly preferred encompass the fol- lowing species: Menthol
  • Physiological warming agents forming group (b2) are chemical substances ini- tiating a warming effect when brought into contact with human skin or mucosa. Suitable warming agents encompass the following species:
  • said warming agent represent a vanillyl ether ac- cording to formula (I) wherein R 1 stands for hydrogen, or a C 1 -C 7 alkyl group; R 2 stands for a C 1 -C 3 alkyl group, R 3 stands for hydrogen or a C 3 -C 9 alkoxyl group; R 4 stands for hydroxyl or a - OC(O)CH 3 group; and wherein R 2 and R 3 can be covalent bounded to form a cyclic acetal; said acetal optionally substituted by a C 2 -C 8 alkyl group.
  • said warming agents represent a vanillyl ether according to formula (II) wherein R 1 stand for hydrogen or a C 1 -C 7 alkyl group.
  • Most preferred said warming agents represent a vanillyl ether according to for- mula (III)
  • Aroma or flavoring compounds are Aroma or flavoring compounds
  • Aroma compounds and flavouring agents forming group (c) are well known in the art and can be chosen from synthetic flavouring liquid and/or oils derived from plants leaves, flowers, fruits and so forth, and combinations thereof.
  • Representative flavouring liquids include: artificial, natural or synthetic fruit flavours such as eucalyp- tus, lemon, orange, banana, grape, lime, apricot and grapefruit oils and fruit essences including apple, strawberry, cherry, orange, pineapple and so forth; bean and nut de- rived flavours such as coffee, cocoa, cola, peanut, almond and so forth; and root de- rived flavours such as licorice or ginger.
  • solid aroma and flavoring compounds for example in the form of salts can be used.
  • Suitable aroma or flavouring compounds encompass the following species:
  • aroma or flavouring compounds encompass menthol, cin- eol, eugenol, thymol, cinnamic aldehyde, peppermint oil, spearmint oil, eucalyptus oil, thyme oil, cinnamon oil, clove oil, spruce needle oil, fennel oil, sage oil, aniseed oil, star anise oil, chamomile oil, and caraway oil, and their mixtures.
  • the fragrances forming group (d) can be used as single components or in the form of more or less complex mixtures.
  • the species may be obtained from natural sources or prepared by organic synthesis.
  • Natural perfumes include the extracts of blossoms (lily, lavender, rose, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, orange), roots (nutmeg, an- gelica, celery, cardamom, costus, iris, calmus), woods (pinewood, sandalwood, guaiac wood, cedarwood, rosewood), herbs and grasses (tarragon, lemon grass, sage, thyme), needles and branches (spruce, fir, pine, dwarf pine), resins and balsams (gal- banum, elemi, benzoin, myrrh, olibanum, opoponax). Animal raw materials, for exam- ple civet and beaver, may also be used.
  • the synthetic fragrances represent aldehydes, ketones, alcohols, ethers, esters, hydrocarbons their mixtures.
  • these types of fragrances are illustrated but not limited by examples:
  • fragrances showing an aldehyde structure encompass melonal, triplal, ligustral, adoxal, anisaldehyde, cymal, ethylvanillin, florhydral, flo- ralozon, helional, heliotropin, hydroxycitronellal, koavon, laurinaldehyde, canthoxal, ly- ral, lilial, adoxal, anisaldehyde, cumal, methyl-nonyl-acetaldehyde, citronellal, citronel- lyloxy-acetaldehyde, cyclamenaldehyde, bourgeonal, p-tert.-bucinal, phenylacetalde- hyde, undecylenaldehyde, vanillin; 2,6,10-trimethyl-9-undecenal, 3-dodecen-l-al, a-n-
  • fragrances showing a ketone structure encompass buc- coxime, iso jasmone, methyl beta naphthyl ketone, moschus indanone, tonalid/mos- chus plus, ⁇ -damascone, ⁇ -damascon, ⁇ -damascone, Iso-damascone, damascenone, damarose, methyl-dihydrojasmonate, menthone, carvone, campher, fenchone, al- phalonen, ⁇ -iononw, dihydro- ⁇ -lonone, y-methylionone, fleuramone, dihydrojasmone, cis-Jasmon, iso-E-Super, methyl cedrenylk etone, or methyl cedrylon, acetophenone, methyl aceto phenone, p-methoxyacetophenone, methyl- ⁇ -napht
  • the preferred ketones are selected from the group comprising a-damascone, ⁇ - damascone, iso-damascone, carvone, ⁇ -methyl ionone, Iso-E-Super, 2,4,4,7-tetrame- thyl-oct-6-en-3-one, benzylacetone, ⁇ -damascone, damascenone, methyl dihydro- jasmonate, methyl cedrylone, hedione and their mixtures
  • said ketones or said aldehydes may show an aliphatic, cycloaliphatic, aromatic, ethylenically unsaturated structure or a mixture of these ele- ments.
  • the components may also include heteroatoms or show a polycyclic structure. Suitable substituents for all these structures are hydroxyl and/or amino groups.
  • Further fragrances are compiled in the following document: Steffen Arctander " Published 1960 and 1969 respectively, Reprinted2000 ISBN: Aroma Chemicals Vol. 1 : 0-931710-37- 5, Aroma Chemicals Vol. 2: 0-931710-38-3”, which is hereby incorporated by refer- ence.
  • Suitable fragrance alcohols encompass for example 10-undecen-1 -ol, 2,6-di- methylheptan-2-ol, 2-methylbutanol, 2-methylpentanol,2-phenoxyethanol, 2-phe- nylpropanol, 2-tert-Butycyclohexanol, 3,5,5-trimethylcyclohexanol, 3-hexanol, 3-me- thyl-5-phenylpentanol, 3-octanol, 1 -octen-3-ol, 3-phenylpropanol,4-heptenol, 4-iso- propylcyclohexanol, 4-tert-butycyclohexanol, 6,8-dimethyl-2-nonanol,6-nonen-1 -ol, 9- decen-1 -ol, ⁇ -methyl benzylalcohol, ⁇ -terpineol, amylsalicylat
  • fragrances showing a ketone structure encompass benzyl acetate, phenoxyisobutyrate, p-tert.-butylcyclohexylacetate, linalylacetate, dime- thylbenzylcarbinylacetate (DMBCA), phenylethylacetate, benzylacetate, ethylme- thylphenylglycinate, allylcyclohexylpropionate, styrallylpropionate, benzylsalicylate, cyclohexylsalicylate, floramat, melusat, jasmacyclatat and their mixtures.
  • fragrances showing a ketone structure encompass ben- zylethyl ether or ambroxan.
  • Hydrocarbons
  • fragrances representing hydrocarbons encompass ter- penes, e.g. limonene and pinen.
  • Fragrances which are particularly preferred encompass the following species:
  • Another object of the present invention refers to cosmetic preparations compris- ing the compositions as defined above.
  • Said cosmetic preparations can represent skin care, personal care, sun care or hair care product or product formulation, comprising the composition as defined above in a working amount, for example about 0.01 to about 1 wt.-percent., preferably about 0.1 to about 0.5 wt.-percent calculated on the composition(s).
  • the composition may represent for example a cosmetic cream, lotion, spray, emulsion, ointment, gel or mousse and the like.
  • the preparations according to the invention may contain antidandruff agents, irritation-preventing agents, irritation-inhibiting agents, antioxidants, astringents, per- spiration-inhibiting agents, antiseptic agents, ant-statics, binders, buffers, carrier ma- terials, chelating agents, cell stimulants, cleansing agents, care agents, deodorizing agents, antiperspirants, softeners, emulsifiers, enzymes, essential oils, fibres, film- forming agents, fixatives, foam-forming agents, foam stabilizers, substances for pre- venting foaming, foam boosters, gelling agents, gel-forming agents, hair care agents, hair-setting agents, hair-straightening agents, moisture-donating agents, moisturizing substances, moisture-retaining substances, bleaching agents, strengthening agents, stain-removing agents, optically brightening agents, impregnating agents, dirt-repellent agents, friction-reducing agents, lubricants, moisturizing creams, ointments, opac
  • auxiliaries and additives are anionic and/or amphoteric or zwitterionic surfactants.
  • Non-ionic and cationic surfactants can be also present in the composition. Suitable examples are mentioned along with the paragraph dealing with emulsifiers.
  • Typical examples for anionic and zwitterionic surfactants encompass: Almon- damidopropylamine Oxide, Almondamidopropyl Betaine, Aminopropyl Laurylgluta- mine, Ammonium C12-15 Alkyl Sulfate, Ammonium C12-16 Alkyl Sulfate, Ammonium Capryleth Sulfate, Ammonium Cocomonoglyceride Sulfate, Ammonium Coco-Sulfate, Ammonium Cocoyl Isethionate, Ammonium Cocoyl Sarcosinate, Ammonium C12-15 Pareth Sulfate, Ammonium C9-10 Perfluoroalkylsulfonate, Ammonium Dinonyl Sul- fosuccinate, Ammonium Dodecylbenzenesulfonate, Ammonium Isostearate, Ammo- nium Laureth-6 Carboxylate, Ammonium Laureth-8 Carboxylate, Ammonium Laureth
  • the percentage content of surfactants in the preparations may be from 0.1 to 10% by weight and is preferably from 0.5 to 5% by weight, based on the preparation.
  • Suitable oil bodies which form constituents of the O/W emulsions, are, for ex- ample, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of linear C 6 -C 22 -fatty acids with linear or branched C 6 -C 22 -fatty alcohols or esters of branched C 6 -C 13 -carboxylic acids with linear or branched C 6 -C 22 - fatty alcohols, such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, cetyl myr
  • esters of linear C 6 -C 22 -fatty acids with branched alcohols in particular 2-ethylhexanol, esters of C 18 -C 38 - alkylhydroxy carboxylic acids with linear or branched C 6 -C 22 -fatty alcohols, in particular Dioctyl Mal- ate, esters of linear and/or branched fatty acids with polyhydric alcohols (such as, for example, propylene glycol, dimerdiol or trimertriol) and/or Guerbet alcohols, triglycer- ides based on C 6 -C 10 -fatty acids, liquid mono-/di-/triglyceride mixtures based on C 6 -C 10 -fatty acids, esters of C 6 - C 22 -fatty alcohols and/or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C 2 - C 12 -dicarboxylic acids with linear or branched alcohols having
  • Finsolv® TN linear or branched, symmetrical or asymmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group, such as, for example, dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicones, silicone methi- cone grades, etc.) and/or aliphatic or naphthenic hydrocarbons, such as, for example, squalane, squalene or dialkylcyclohexanes.
  • dicaprylyl ether such as, for example, dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicones, silicone methi- cone grades, etc.) and/or aliphatic or naphthenic hydrocarbons, such as, for example, squalane, squalen
  • non-ionic or cationic surfactants may also be added to the preparations as emulsifiers, including for example:
  • polyol esters and, in particular, polyglycerol esters such as, for example, polygly- cerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol di- merate isostearate. Mixtures of compounds from several of these classes are also suitable; • Addition products of 2 to 15 mol ethylene oxide onto castor oil and/or hydrogen- ated castor oil;
  • the Addition products of ethylene oxide and/or propylene oxide onto fatty alco- hols, fatty acids, alkylphenols, glycerol mono- and diesters and sorbitan mono- and diesters of fatty acids or onto castor oil are known commercially available products. They are homologue mixtures of which the average degree of alkoxylation corresponds to the ratio between the quantities of ethylene oxide and/or propylene oxide and sub- strate with which the Addition reaction is carried out. C 12/18 fatty acid monoesters and diesters of Addition products of ethylene oxide onto glycerol are known as lipid layer enhancers for cosmetic formulations.
  • the preferred emulsifiers are described in more detail as follows:
  • Partial glycerides Typical examples of suitable partial glycerides are hy- droxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid monoglyceride, isostearic acid diglyceride, oleic acid monoglyceride, oleic acid diglyc- eride, ricinoleic acid monoglyceride, ricinoleic acid diglyceride, linoleic acid mono- glyceride, linoleic acid diglyceride, linolenic acid monoglyceride, linolenic acid diglyc- eride, erucic acid monoglyceride, erucic acid diglyceride, tartaric acid monoglyceride, tartaric acid diglyceride, citric acid monoglyceride, citric acid diglyceride, malic acid monoglyceride, malic acid diglyceride and technical
  • Sorbitan esters are sorbitan monoisostearate, sorbi- tan sesquiisostearate, sorbitan diisostearate, sorbitan triisostearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate, sorbitan mo- noerucate, sorbitan sesquierucate, sorbitan dierucate, sorbitan trierucate, sorbitan monoricinoleate, sorbitan sesquiricinoleate, sorbitan diricinoleate, sorbitan triricinole- ate, sorbitan monohydroxystearate, sorbitan sesquihydroxystearate, sorbitan dihy- droxystearate, sorbitan trihydroxystearate, sorbitan monotartrate, sorbitan sesquitar- trate, sorbitan di
  • Polyglycerol esters are Pol- yglyceryl-2 Dipolyhydroxystearate (Dehymuls® PG PH), Polyglycerin-3-Diisostearate (Lameform® TGI), Polyglyceryl-4 Isostearate (Isolan® Gl 34), Polyglyceryl-3 Oleate, Diisostearoyl Polyglyceryl-3 Diisostearate (Isolan® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care® 450), Polyglyceryl-3 Beeswax (Cera Beilina®), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010/90), Polyglyceryl-3 Cetyl Ether (Chimexane® NL), Polyglyceryl-3 Distearate (Cremophor® GS 32) and Polyglyceryl Polyricinoleate (Ad
  • Exam- ples of other suitable polyolesters are the mono-, di- and triesters of trimethylol pro- pane or pentaerythritol with lauric acid, cocofatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like optionally reacted with 1 to 30 mol ethylene oxide.
  • Cationically active surfactants comprise the hydrophobic high molecular group required for the surface activity in the cation by dissociation in aqueous solution.
  • a group of important representatives of the cationic surfactants are the tetraalk(en)yl ammonium salts of the general formula: (R 1 R 2 R 3 R 4 N + ) X-.
  • R 1 stands for C 1 -C 8 alk(en)yl, R 2 , R 3 and R 4 , independently of each other, for alk(en)yl groups having 1 to 22 carbon atoms.
  • X is a counter ion, preferably selected from the group of the halides, alkyl sulfates and alkyl carbonates.
  • Cationic surfactants in which the nitrogen group is substituted with two long acyl groups and two short alk(en)yl groups, are particularly preferred.
  • Esterquats A further class of cationic surfactants particularly useful as co- surfactants for the present invention is represented by the so-called esterquats.
  • Esterquats are generally understood to be quaternised fatty acid triethanolamine ester salts. These are known compounds which can be obtained by the relevant methods of preparative organic chemistry. Reference is made in this connection to International patent application WO 91/01295 A1 , according to which triethanolamine is partly esterified with fatty acids in the presence of hypophosphorous acid, air is passed through the reaction mixture and the whole is then quaternised with dimethyl sulphate or ethylene oxide.
  • German patent DE 4308794 C1 describes a process for the production of solid esterquats in which the quaternisation of triethanolamine esters is carried out in the presence of suitable dispersants, preferably fatty alcohols.
  • suitable dispersants preferably fatty alcohols.
  • Typical examples of esterquats suitable for use in accordance with the invention are products of which the acyl component derives from monocarboxylic acids corresponding to formula RCOOH in which RCO is an acyl group containing 6 to 10 carbon atoms, and the amine component is triethanolamine (TEA).
  • monocarboxylic acids are caproic acid, caprylic acid, capric acid and technical mixtures thereof such as, for example, so-called head-fractionated fatty acid.
  • Esterquats of which the acyl component derives from monocarboxylic acids containing 8 to 10 carbon atoms are preferably used.
  • Other esterquats are those of which the acyl component derives from dicarboxylic acids like malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, sorbic acid, pimelic acid, azelaic acid, sebacic acid and/or dodecanedioic acid, but preferably adipic acid.
  • esterquats of which the acyl component derives from mixtures of monocarboxylic acids containing 6 to 22 carbon atoms, and adipic acid are preferably used.
  • the molar ratio of mono and dicarboxylic acids in the final esterquat may be in the range from 1 :99 to 99:1 and is preferably in the range from 50:50 to 90:10 and more particularly in the range from 70:30 to 80:20.
  • other suitable esterquats are quaternized ester salts of mono-/dicarboxylic acid mixtures with diethanolalkyamines or 1 ,2-dihydroxypropyl dialkylamines.
  • the esterquats may be obtained both from fatty acids and from the corresponding triglycerides in admixture with the corresponding dicarboxylic acids.
  • Superfatting agents may be selected from such substances as, for example, lanolin and lecithin and also polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the fatty acid alkanolamides also serving as foam stabilizers.
  • the consistency factors mainly used are fatty alcohols or hydroxyfatty alcohols containing 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycerides, fatty acids or hydroxyfatty acids.
  • a combination of these substances with alkyl oli- goglucosides and/or fatty acid N-methyl glucamides of the same chain length and/or polyglycerol poly-12-hydroxystearates is preferably used.
  • Suitable thickeners are polymeric thickeners, such as Aerosil® types (hydro- philic silicas), polysaccharides, more especially xanthan gum, guar-guar, agar-agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, also rela- tively high molecular weight polyethylene glycol monoesters and diesters of fatty acids, polyacrylates (for example Carbopols® [Goodrich] or Synthalens® [Sigma]), poly- acrylamides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as, for ex- ample, ethoxylated fatty acid glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylol propane, narrow-range fatty alcohol ethoxylates and elec- trolytes, such as sodium chloride and ammonium chloride.
  • Suitable cationic polymers are, for example, cationic cellulose derivatives such as, for example, the quaternized hydroxyethyl cellulose obtainable from Amerchol un- der the name of Polymer JR 400®, cationic starch, copolymers of diallyl ammonium salts and acrylamides, quaternized vinyl pyrrolidone/vinyl imidazole polymers such as, for example, Luviquat® (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides such as, for example, Lauryldimonium Hydroxypro- pyl Hydrolyzed Collagen (Lamequat® L, Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as, for example, amodimethicone, copolymers of adipic acid and dimethylaminohydroxypropyl diethylenetriamine (Car- taretine®, Sandoz),
  • Suitable anionic, zwitterionic, amphoteric and nonionic polymers are, for exam- ple, vinyl acetate/crotonic acid copolymers, vinyl pyrrolidone/vinyl acrylate copolymers, vinyl acetate/butyl maleate/isobornyl acrylate copolymers, methyl vinylether/maleic an- hydride copolymers and esters thereof, uncrosslinked and polyol-crosslinked poly- acrylic acids, acrylamidopropyl trimethylammonium chloride/acrylate copolymers, oc- tylacrylamide/methyl methacrylate/tert.-butylaminoethyl methacrylate/2-hydroxypropyl methacrylate copolymers, polyvinyl pyrrolidone, vinyl pyrrolidone/vinyl acetate copoly- mers, vinyl pyrrolidone/dimethylaminoethyl methacrylate/viny
  • Suitable pearlizing waxes are, for example, alkylene glycol esters, especially ethylene glycol distearate; fatty acid alkanolamides, especially cocofatty acid diethan- olamide; partial glycerides, especially stearic acid monoglyceride; esters of polybasic, optionally hydroxysubstituted carboxylic acids with fatty alcohols containing 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; fatty compounds, such as for example fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty car- bonates which contain in all at least 24 carbon atoms, especially laurone and dis- tearylether; fatty acids, such as stearic acid, hydroxystearic acid or behenic acid, ring opening products of olefin epoxides containing 12 to 22 carbon atoms with fatty alco- hols containing 12 to 22 carbon atoms and/or polyo
  • Suitable silicones can be chosen from the group consisting of: Acefylline Methylsilanol Mannuronate, Acetylmethionyl Methylsilanol Elastinate Acrylates/Be- henyl, Acrylate/Dimethicone Methacrylate Copolymer, Acrylates/Behenyl Methacry- late/Dimethicone Methacrylate Copolymer, Acrylates/Bis-Hydroxypropyl Dimethicone Crosspolymer, Acrylates/Dimethicone Copolymer, Acrylates/Dimethicone Methacry- late/Ethylhexyl Acrylate Copolymer, Acrylates/Dimethiconol Acrylate Copolymer, Acry- lates/Ethylhexyl Acrylate/Dimethicone Methacrylate Copolymer, Acrylates/Octylacryla- mide/Diphen
  • silicones to be contained in the mixture according to the inventions are Dimethicone, Cyclomethicone, Phenyl Trimethicone, Cyclohexasilox- ane and Cyclopentasiloxane.
  • suitable volatile silicones can be found in Todd et al. in Cosm. Toil. 91 , 27 (1976).
  • waxes may also be present in the preparations, more especially natural waxes such as, for example, candelilla wax, carnauba wax, Japan wax, espartograss wax, cork wax, guaruma wax, rice oil wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, spermaceti, lanolin (wool wax), uro- pygial fat, ceresine, ozocerite (earth wax), petrolatum, paraffin waxes and microwaxes; chemically modified waxes (hard waxes) such as, for example, montan ester waxes, sasol waxes, hydrogenated jojoba waxes and synthetic waxes such as, for example, polyalkylene waxes and polyethylene glycol waxes.
  • natural waxes such as, for example, candelilla wax, carnauba wax, Japan wax, espartograss wax, cork wax,
  • Metal salts of fatty acids such as, for example, magnesium, aluminium and/or zinc stearate or ricinoleate may be used as stabilizers.
  • Primary sun protection filters such as, for example, magnesium, aluminium and/or zinc stearate or ricinoleate may be used as stabilizers.
  • Primary sun protection filters in the context of the invention are, for example, organic substances (light filters) which are liquid or crystalline at room temperature and which are capable of absorbing ultraviolet radiation and of releasing the energy ab- sorbed in the form of longer-wave radiation, for example heat.
  • the formulations according to the invention advantageously contain at least one UV-A filter and/or at least one UV-B filter and/or a broadband filter and/or at least one inorganic pigment.
  • Formulations according to the invention preferably contain at least one UV-B filter or a broadband filter, more particularly preferably at least one UV- A filter and at least one UV-B filter.
  • UV filters cited below which can be used within the context of the present invention are preferred but naturally are not limiting. UV filters which are preferably used are selected from the group consisting of one, two, three, four, five or more of the following species:
  • the sun protection filter forming component (ii) rep- resents a blend of UV-A- and UV-B-filters selected from the group consisting of ho- mosalate, octocrylene, bis-ethylhexyloxyphenol methoxyphenyl triazine, butyl methox- ydibenzoylmethane, ethylhexyl salicylate and mixtures thereof.
  • Particular preferred is a blend of all these filters which is commercially available in the market under the trademark NeoHeliopan® Flat (SYMRISE), which also subject to WO 2020 088778 A1 .
  • Suitable pigments encompass oxides of titanium (TiO 2 ), zinc (ZnO), iron (Fe 2 O 3 ), zirconium (ZrO 2 ), silicon (SiO 2 ), manganese (e.g. MnO), aluminium (AI 2 O 3 ), cerium (e.g. Ce 2 O 3 ) and/or mixtures thereof.
  • a formulation according to the invention con- tains a total amount of sunscreen agents, i.e. in particular UV filters and/or inorganic pigments (UV filtering pigments) so that the formulation according to the invention has a light protection factor of greater than or equal to 5 and up to 50.
  • sunscreen agents i.e. in particular UV filters and/or inorganic pigments (UV filtering pigments) so that the formulation according to the invention has a light protection factor of greater than or equal to 5 and up to 50.
  • UV filters and/or inorganic pigments UV filtering pigments
  • sec- ondary sun protection factors of the antioxidant type may also be used.
  • Secondary sun protection factors of the antioxidant type interrupt the photochemical reaction chain which is initiated when UV rays penetrate into the skin.
  • Typical examples are amino acids (for example glycine, histidine, tyrosine, tryptophane) and derivatives thereof, imidazoles (for example urocanic acid) and derivatives thereof, peptides, such as D,L- carnosine, D-carnosine, L-carnosine and derivatives thereof (for example anserine), carotinoids, carotenes (for example alpha-carotene, beta-carotene, lycopene) and de- rivatives thereof, chlorogenic acid and derivatives thereof, liponic acid and derivatives thereof (for example dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (for example thioredoxine, glutathiouracil and other thiols (
  • Advantageous inorganic secondary light protection pigments are finely dis- persed metal oxides and metal salts which are also mentioned in WO 2005 123101 A1 .
  • the total quantity of inorganic pigments, in particular hydrophobic inorganic micro- pigments in the finished cosmetic preparation according to the present invention is advantageously from 0.1 to 30% by weight, preferably 0.5 to 10.0% by weight, in each case based on the total weight of the preparation.
  • particulate UV filters or inorganic pigments which can op- tionally be hydrophobed, can be used, such as the oxides of titanium (TiO 2 ), zinc (ZnO), iron (Fe 2 O 3 ), zirconium (ZrO 2 ), silicon (SiO 2 ), manganese (e.g. MnO), alumin- ium (AI 2 O 3 ), cerium (e.g. Ce 2 O 3 ) and/or mixtures thereof.
  • Biogenic active substances include, for example, tocopherol, tocopherol ace- tate, tocopherol palmitate, ascorbic acid, (deoxy)ribonucleic acid and its fragmentation products, ⁇ -glucans, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts, such as such as prunus extract, bambaranus extract and vitamin complexes.
  • Antioxidants interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin.
  • Typical examples are amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides like D,L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. -carotene, lycopene) and their derivates, chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g.
  • dihy- drolic acid aurothioglucose
  • propylthiouracil and other thiols e.g. thioredoxin, gluta- thione, cysteine, cystine, cystamin and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, linoleyl, cholesteryl and glyceryl esters
  • hydroxy acids e.g. buthionine sulfoximines, homocysteine sul- foximines, butionine sulfones, penta-, hexa-, heptathionine sulfoximines
  • very low tolerated dosages e.g. pmol to mol/kg
  • furthermore (metal) chelators e.g. hydroxy fatty acids, palmitic acid, phytinic acid, lactoferrin), hydroxy acids (e.g.
  • citric acid citric acid, lactic acid, malic acid
  • humic acid gallic acid
  • bile extracts bilirubin, biliverdin, EDTA, EGTA and their derivatives
  • unsaturated fatty acids and their derivatives e.g. linolenic acid, linoleic acid, oleic acid
  • folic acid and its derivatives ubiquinone and ubiquinol and their derivatives
  • vitamin C and its derivatives e.g. ascorbyl palmitate, Mg-ascorbyl phosphate, ascorbylacetate
  • tocopherols and derivatives e.g.
  • vitamin E acetate vitamin E acetate
  • vit- amin A and derivates vitamin A palmitate
  • conifer aryl benzoate of benzoic resin rutinic acid and its derivatives, glycosylrutin, ferulic acid, furfurylidene glucitol, carnosine, butyl hydroxytoluene, butylhydroxyanisole, nordihydroguaiac resin acid, nordihydroguajaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, man- nose and its derivatives, superoxide dismutase, zinc and its derivatives (e.g. ZnO, ZnSO 4 ) selenium and its derivatives (e.g.
  • stilbenes and their derivatives e.g. styrene oxide, trans-stilbene oxide
  • derivatives suitable for the invention salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids
  • Preferred active ingredients for hair lightening are selected from the group con- sisting of: kojic acid (5-hydroxy-2-hydroxymethyl-4-pyranone), kojic acid derivatives, preferably kojic acid dipalmitate, arbutin, ascorbic acid, ascorbic acid derivatives, pref- erably magnesium ascorbyl phosphate, hydroquinone, hydroquinone derivatives, res- orcinol, resorcinol derivatives, preferably 4-alkylresorcinols and 4-(1 -phenylethyl)1 ,3- dihydroxybenzene (phenylethyl resorcinol), cyclohexylcarbamates (preferably one or more cyclohexyl carbamates disclosed in WO 2010/122178 and WO 2010/097480), sulfur-containing molecules, preferably glutathione or cysteine, alpha-hydroxy acids (preferably citric acid, lactic acid, malic acid), salts and esters thereof,
  • Advantageous skin and hair tanning active ingredients in this respect are sub- strates or substrate analogues of tyrosinase such as L-tyrosine, N-acetyl tyrosine, L- DOPA or L-dihydroxyphenylalanine, xanthine alkaloids such as caffeine, theobromine and theophyl-line and derivatives thereof, proopiomelanocortin peptides such as ACTH, alpha-MSH, peptide analogues thereof and other substances which bind to the melanocortin receptor, peptides such as Val-Gly-Val-Ala-Pro-Gly, Lys-lle- Gly-Arg-Lys or Leu-lle-Gly-Lys, purines, pyrimidines, folic acid, copper salts such as copper glu- conate, chloride or pyrrolidonate, 1 ,3,4-oxadiazole-2-thiols such as 5-pyr
  • Flavonoids which bring about skin and hair tinting or brown-ing (e.g. quercetin, rhamnetin, kaempferol, fisetin, genistein, daidzein, chrysin and api-genin, epicatechin, diosmin and diosmetin, morin, quercitrin, naringenin, hesperidin, phloridzin and phloretin) can also be used.
  • brown-ing e.g. quercetin, rhamnetin, kaempferol, fisetin, genistein, daidzein, chrysin and api-genin, epicatechin, diosmin and diosmetin, morin, quercitrin, naringenin, hesperidin, phloridzin and phloretin
  • the amount of the aforementioned examples of Additional active ingredients for the modulation of skin and hair pigmentation (one or more compounds) in the prod- ucts according to the invention is then preferably 0.00001 to 30 wt.%, preferably 0.0001 to 20 wt.%, particularly preferably 0.001 to 5 wt.%, based on the total weight of the preparation.
  • Hair growth activators or inhibitors are preferably 0.00001 to 30 wt.%, preferably 0.0001 to 20 wt.%, particularly preferably 0.001 to 5 wt.%, based on the total weight of the preparation.
  • Formulations and products according to the present invention may also com- prise one or more hair growth activators, i.e. agents to stimulate hair growth.
  • Hair growth activators are preferably selected from the group consisting of pyrimidine de- rivatives such as 2,4-diaminopyrimidine-3-oxide (Aminexil), 2,4-diamino-6-piperidino- pyrimidine-3-oxide (Minoxidil) and derivatives thereof, 6-amino-1 ,2-dihydro-1 -hydroxy- 2-imino-4-piperidinopyrimidine and its derivatives, xanthine alkaloids such as caffeine, theobromine and theophylline and derivatives thereof, quercetin and derivatives, dihy- droquercetin (taxifolin) and derivatives, potassium channel openers, antiandrogenic agents, synthetic or natural 5-reductase inhibitors, nicotinic acid esters such as to- copheryl nicotinate,
  • formulations and products according to the present invention may comprise one or more hair growth inhibitors (as described above), i.e. agents to reduce or prevent hair growth.
  • Hair growth inhibitors are preferably selected from the group consisting of activin, activin derivatives or activin agonists, ornithine decarbox- ylase inhibitors such as alpha-difluoromethylornithine or pentacyclic triterpenes like for example ursolic acid, betulin, betulinic acid, oleanolic acid and derivatives thereof, 5al- pha-reductase inhibitors, androgen receptor antagonists, S-adenosylmethionine de- carboxylase inhibitors, gamma-glutamyl transpeptidase inhibitors, transglutaminase inhibitors, soybean-derived serine protease inhibitors, extracts from microorganisms, algae, different microalgae or plants and plant parts of for example the families Legu- min
  • Suitable anti-inflammatory agents may be selected from the group formed by:
  • steroidal anti-inflammatory substances of the corticosteroid type in particular hydrocortisone, hydrocortisone derivatives such as hydrocortisone 17-butyrate, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone,
  • non-steroidal anti-inflammatory substances in particular oxicams such as pirox- icam or tenoxicam, salicylates such as aspirin, disalcid, solprin or fendosal, ace- tic acid derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin or clindanac, fenamates such as mefenamic, meclofenamic, flufenamic or niflumic, propionic acid derivatives such as ibuprofen, naproxen or be- noxaprofen, pyrazoles such as phenylbutazone, oxyphenylbutazone, febrazone or azapropazone,
  • oxicams such as pirox- icam or tenoxicam
  • salicylates such as aspirin, disalcid, solprin or fendosal
  • ace- tic acid derivatives such as diclofenac,
  • histamine receptor antagonists include serine protease inhibitors (e.g. of Soy extracts), TRPV1 antagonists (e.g. 4-t-Butylcyclohexanol), NK1 antagonists (e.g. Aprepi- tant, Hydroxyphenyl Propamidobenzoic Acid), cannabinoid receptor agonists (e.g. Palmitoyl Ethanolamine) and TRPV3 antagonists.
  • serine protease inhibitors e.g. of Soy extracts
  • TRPV1 antagonists e.g. 4-t-Butylcyclohexanol
  • NK1 antagonists e.g. Aprepi- tant, Hydroxyphenyl Propamidobenzoic Acid
  • cannabinoid receptor agonists e.g. Palmitoyl Ethanolamine
  • TRPV3 antagonists e.g. Palmitoyl Ethanolamine
  • Suitable anti-microbial agents are, in principle, all substances effective against Gram-positive bacteria, such as, for example, 4- hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4- dichlorophenyl)urea, 2,4,4'-trichloro-2'-hydroxy-di- phenyl ether (triclosan), 4-chloro-3,5-dimethyl-phenol, 2,2'-methylenebis(6-bromo-4- chlorophenol), 3-methyl-4-(1 -methylethyl)phenol, 2-benzyl-4-chloro-phenol, 3-(4-chlo- rophenoxy)-1 ,2-propanediol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'- trichlorocarbanilide (TTC), antibacterial fragrances, thymol, thyme oil, eugenol,
  • Suitable enzyme inhibitors are, for example, esterase inhibitors. These are preferably trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and, in particular, triethyl citrate (Hydagen CAT). The substances inhibit enzyme activity, thereby reducing the formation of odour.
  • esterase inhibitors such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and, in particular, triethyl citrate (Hydagen CAT).
  • esterase inhibitors are sterol sulfates or phosphates, such as, for example, lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and esters thereof, such as, for example, glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and esters thereof, such as, for example, citric acid, malic acid, tartaric acid or diethyl tartrate, and zinc glycinate.
  • sterol sulfates or phosphates such as, for example, lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate
  • dicarboxylic acids and esters thereof such as, for example, glutaric acid, monoethy
  • Suitable odour absorbers are substances which are able to absorb and largely retain odour-forming compounds. They lower the partial pressure of the individual com- ponents, thus also reducing their rate of diffusion. It is important that perfumes must remain unimpaired in this process. Odour absorbers are not effective against bacteria. They comprise, for example, as main constituent, a complex zinc salt of ricinoleic acid or specific, largely odour-neutral fragrances which are known to the person skilled in the art as "fixatives", such as, for example, extracts of labdanum or styrax or certain abietic acid derivatives.
  • the odour masking agents are fragrances or perfume oils, which, in Addition to their function as odour masking agents, give the deodorants their respective fragrance note.
  • Perfume oils which may be mentioned are, for example, mixtures of natural and synthetic fragrances. Natural fragrances are extracts from flow- ers, stems and leaves, fruits, fruit peels, roots, woods, herbs and grasses, needles and branches, and resins and balsams. Also suitable are animal products, such as, for example, civet and castoreum.
  • Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol, and hydrocarbon type.
  • Fragrance com- pounds of the ester type are, for example, benzyl acetate, p-tert-butylcyclohexyl ace- tate, linalyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, allyl cyclo- hexylpropionate, styrallyl propionate and benzyl salicylate.
  • the ethers include, for ex- ample, benzyl ethyl ether
  • the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal
  • the ketones include, for example, the ionones and methyl cedryl ketone
  • the alcohols include anethole, citronellol, euge- nol, isoeugenol, geraniol, linaool, phenylethyl alcohol and terpineol
  • the hydrocar- bons include mainly the terpenes and balsams.
  • Es- sential oils of relatively low volatility which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, camomile oil, oil of cloves, melissa oil, mint oil, cinnamon leaf oil, linden flower oil, juniperberry oil, vetiver oil, olibanum oil, galba- num oil, labdanum oil and lavandin oil.
  • Suitable astringent antiperspirant active ingredients are primarily salts of alu- minium, zirconium or of zinc.
  • Such suitable antihydrotic active ingredients are, for ex- ample, aluminium chloride, aluminium chlorohydrate, aluminium dichlorohydrate, alu- minium sesquichlorohydrate and complex compounds thereof, e.g. with 1 ,2- propylene glycol, aluminium hydroxyallantoinate, aluminium chloride tartrate, aluminium zirco- nium trichlorohydrate, aluminium zirconium tetrachlorohydrate, aluminium zirconium pentachlorohydrate and complex compounds thereof, e.g. with amino acids, such as glycine.
  • Standard film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone/vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyalu- ronic acid and salts thereof and similar compounds.
  • Suitable antidandruff agents are Pirocton Olamin (1 -hydroxy-4-methyl-6- (2,4,4-trimethylpentyl)-2-(1 H)-pyridinone monoethanolamine salt), Baypival® (Climba- zole), Ketoconazol® (4-acetyl-1 - ⁇ 4-[2-(2,4-dichlorophenyl) r-2-(1 H-imidazol-1 -ylme- thyl)-1 ,3-dioxylan-c-4-ylmethoxyphenyl ⁇ -piperazine, ketoconazole, elubiol, selenium disulfide, colloidal sulfur, sulfur polyethylene glycol sorbitan monooleate, sulfur ricinol polyethoxylate, sulfur tar distillate, salicylic acid (or in combination with hexachloro- phene), undecylenic acid, monoethanolamide sulfosuccinate Na salt, Lamepon®
  • Preferred cosmetics carrier materials are solid or liquid at 25°C and 1013 mbar (including highly viscous substances) as for example glycerol, 1 ,2-propylene glycol, 1 ,2-butylene glycol, 1 ,3-propylene glycol, 1 ,3-butylene glycol, ethanol, water and mix- tures of two or more of said liquid carrier materials with water.
  • these prep- arations according to the invention may be produced using preservatives or solubil- izers.
  • Other preferred liquid carrier substances which may be a component of a prep- aration according to the invention are selected from the group consisting of oils such as vegetable oil, neutral oil and mineral oil.
  • Preferred solid carrier materials which may be a component of a preparation according to the invention are hydrocolloids, such as starches, degraded starches, chemically or physically modified starches, dextrins, (powdery) maltodextrins (prefera- bly with a dextrose equivalent value of 5 to 25, preferably of 10 - 20), lactose, silicon dioxide, glucose, modified celluloses, gum arabic, ghatti gum, traganth, karaya, carra- geenan, pullulan, curdlan, xanthan gum, gellan gum, guar flour, carob bean flour, algi- nates, agar, pectin and inulin and mixtures of two or more of these solids, in particular maltodextrins (preferably with a dextrose equivalent value of 15 - 20), lactose, silicon dioxide and/or glucose.
  • hydrocolloids such as starches, degraded starches, chemically or
  • hydrotropes for example ethanol, isopropyl alcohol or polyols
  • Suitable polyols preferably contain 2 to 15 carbon atoms and at least two hydroxyl groups.
  • the polyols may contain other functional groups, more especially amino groups, or may be modified with nitrogen. Typical ex- amples are
  • alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propyl- ene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an av- erage molecular weight of 100 to 1000 Dalton;
  • methylol compounds such as, in particular, trimethylol ethane, trimethylol pro- pane, trimethylol butane, pentaerythritol and dipentaerythritol;
  • lower alkyl glucosides particularly those containing 1 to 8 carbon atoms in the alkyl group, for example methyl and butyl glucoside;
  • sugar alcohols containing 5 to 12 carbon atoms for example sorbitol or mannitol
  • sugars containing 5 to 12 carbon atoms for example glucose or sucrose
  • dialcoholamines such as diethanolamine or 2-aminopropane-1 ,3-diol.
  • Suitable preservatives are, for example, phenoxyethanol, sodium benzoate or sorbic acid, blends of the mentioned ingredients and the other classes of compounds listed in Appendix 6, Parts A and B of the Kosmetikverowski (“Cosmetics Directive”).
  • Alternative products which could improve the product protection are for example 1 ,2- alkanediols such as for example 1 ,2-penatnediol, 1 ,2-hexanediol, 1 ,2-octanediol, 1 ,2- decanediol, 1 ,2-dodecanediol and mixtures thereof, 4-hydroxy acetophenone.
  • Suitable dyes are any of the substances suitable and approved for cosmetic purposes as listed, for example, in the publication “Kosmetician mistake für” of the Farbstoffkommission der Deutschen Deutschen Deutschen Deutschen Deutschen Deutschen Deutschen Deutschen Deutschen Deutschen Anlagenstechnik, Verlag Chemie, Weinheim, 1984, pages 81 to 106. Examples include cochineal red A (C.l. 16255), patent blue V (C.l. 42051 ), indigotin (C.l. 73015), chlorophyllin (C.l. 75810), quinoline yellow (C.l. 47005), titanium dioxide (C.l. 77891 ), indanthrene blue RS (C.l. 69800) and mAder lake (C.l. 58000).
  • cochineal red A C.l. 16255
  • patent blue V C.l. 42051
  • indigotin C.l. 73015
  • chlorophyllin C.l. 75810
  • quinoline yellow C.l. 47005
  • titanium dioxide C
  • Luminol may also be present as a luminescent dye.
  • Advantageous coloured pigments are for example titanium dioxide, mica, iron oxides (e.g. Fe 2 O 3 Fe 3 O 4 , FeO(OH)) and/or tin oxide.
  • Advantageous dyes are for example carmine, Berlin blue, chromium oxide green, ultramarine blue and/or manganese vio- let.
  • compositions according to the present inventions are selected from the group of products for treatment, protecting, care and cleansing of the skin and/or hair or as a make-up product, preferably as a leave-on product (meaning that the one or more compounds stay on the skin and/or hair for a longer period of time, compared to rinse-off products).
  • the formulations according to the invention are preferably in the form of an emulsion, e.g. W/O (water-in-oil), O/W (oil-in-water), W/O/W (water-in-oil-in-water), O/W/O (oil-in-water-in-oil) emulsion, PIT emulsion, Pickering emulsion, emulsion with a low oil content, micro- or nanoemulsion, a solution, e.g.
  • a gel including hydrogel, hydrodispersion gel, oleogel
  • spray e.g. pump spray or spray with propellant
  • a foam or an impregnating solution for cosmetic wipes e.g. soap, synthetic detergent, liquid washing, shower and bath preparation, bath product (capsule, oil, tablet, salt, bath salt, soap, etc.), effervescent preparation, a skin care product such as e.g.
  • an emulsion as described above, ointment, paste, gel (as de- scribed above), oil, balsam, serum, powder (e.g. face powder, body powder), eau de perfume, eau de toilette, after-shave, a mask, a pencil, stick, roll-on, pump, aerosol (foaming, non-foaming or post-foaming), a deodorant and/or antiperspirant, mouth- wash and mouth rinse, a foot care product (including keratolytic, deodorant), an insect repellent, a sunscreen, aftersun preparation, a shaving product, aftershave balm, pre- and aftershave lotion, a depilatory agent, a hair care product such as e.g.
  • shampoo including 2-in-1 shampoo, anti-dandruff shampoo, baby shampoo, shampoo for dry scalps, concentrated shampoo
  • conditioner e.g. gel or wax
  • hair smoothing agent e.g. temporary direct- dyeing hair dye, semi-permanent hair dye, permanent hair dye, hair conditioner, hair mousse, eye care product, make-up, make-up remover or baby product.
  • Auxiliary substances and additives can be included in quantities of 5 to 99 % b.w., preferably 10 to 80 % b.w., based on the total weight of the formulation.
  • the amounts of cosmetic or dermatological auxiliary agents and additives and perfume to be used in each case can easily be determined by the person skilled in the art by simple trial and error, depending on the nature of the particular product.
  • the preparations can also contain water in a quantity of up to 99 wt.-percent., preferably from about 5 to about 80 wt.-percent and more preferably either from about 10 to about 50 or from about 60 to about 80 wt.-percent based on the total weight of the preparation.
  • Another object of the present invention is directed to a preferably non- therapeutic oral and/or oral care composition.
  • suitable oral com- positions encompass (hard boiled) candies, compressed tablets, chewing gums, tooth- pastes and mouth washes.
  • the manufacture and composition of said oral composi- tions are described as follows:
  • the preferred candies are so-called hard boiled candies.
  • Their bases are usually prepared from a mixture of sugar and other carbohydrates that are kept in an amorphous or glassy condition.
  • This form can be considered a solid syrup of sugars generally having up to about 4.5 % b.w. moisture, based on the weight of the candy base, with about 0.5 to about 2.5 % b.w. being preferred and about 1 .0 to about 1 .5 % b.w. being most preferred.
  • Such materials nor- mally contain up to 65 % b.w. corn syrup, up to 80 % b.w. sugar and from 0.1 to 5.0 % b.w. water.
  • the ratio of sugar (or other sweetener suitable for candy formu- lation) to corn syrup is within the range of about 70:25 to about 45:55 with about 60:40 being preferred.
  • the syrup component generally is prepared from corn syrups high in fructose, but may include other materials. Further ingredients such as flavourings, sweeteners, acidulents, colorants and so forth may also be added.
  • Hard boiled candy bases may also be prepared from non-fermentable sugars such as sorbitol, mannitol, xylitol, maltitol, hydrogenated starch hydrolysate, hydrogen- ated corn syrup and mixtures thereof.
  • the candy bases may contain up to about 95% sorbitol, a mixture of sorbitol and mannitol at a ratio of about 9.5 to 0.5 up to about 7.5 to 2.5 and hydrogenated corn syrup up to about 55% of the syrup component.
  • the oral compositions can represent com- pressed tablets, comprising the liquid flavour in amounts of typically about 0.1 to about 0.6 % b.w. and preferably about 0.5 % b.w.
  • Chewing gums typically consist of a water- insoluble vase component, a water- soluble component and additives providing for example a specific flavour.
  • the water-insoluble base which is also known as the "gum base” typically comprises natural or synthetic elastomers, resins, fats and oils, plasticizers, fillers, sof- teners, dyes and optionally waxes.
  • the base normally makes up 5 to 95% by weight, preferably 10 to 50% by weight and more particularly 20 to 35% by weight of the com- position as a whole.
  • the base consists of 20 to 60% by weight synthetic elastomers, 0 to 30% by weight natural elastomers, 5 to 55% by weight plasticizers, 4 to 35% by weight fillers, 5 to 35% by weight softeners and small amounts of additives, such as dyes, antioxidants and the like, with the pro- viso that they are soluble in water at best in small quantities.
  • Suitable synthetic elastomers are, for example, polyisobutylenes with average molecular weights (as measured by GPC) of 10,000 to 100,000 dalton and preferably 50,000 to 80,000 dalton, isobutylene/isoprene copolymers ("butyl elastomers”), sty- rene/butadiene copolymers (styrene:butadiene ratio, for example, 1 :3 to 3:1 ).
  • polyvinyl acetates with average molecular weights (as measured by GPC) of 2,000 to 90,000 dalton and preferably 10,000 to 65,000 dalton, polyisoprenes, poly-ethylenes, vinyl ac- etate/vinyl laurate copolymers and mixtures thereof.
  • suitable natural elas- tomers are rubbers, such as for example smoked or liquid latex or guayuls, and natural gums, such as jelutong, lechi caspi, perillo, sorva, massaranduba balata, massa- randuba chocolate, nispero, rosindinba, chicle, gutta hang kang and mixtures thereof.
  • the choice of the synthetic and natural elastomers and their mixing ratios essentially depends on whether or not bubbles are to be produced with the chewing gums (bubble gums). Elastomer mixtures containing jelutong, chicle, sorva and massaranduba are preferably used.
  • plasticizers are, above all, esters of resin acids, for example esters of lower aliphatic alcohols or polyols with completely or partly hydrogenated, monomeric or oligomeric resin acids.
  • esters of resin acids for example esters of lower aliphatic alcohols or polyols with completely or partly hydrogenated, monomeric or oligomeric resin acids.
  • the methyl, glycerol or pentaerythritol esters or mixtures thereof are used for this purpose.
  • terpene resins which may be derived from .alpha.-pinene, .beta.-pinene, .delta.-limo- nene or mixtures thereof, could also be used.
  • Suitable fillers or texturizers are magnesium or calcium carbonate, ground pumice stone, silicates, especially magnesium or aluminium silicates, clays, aluminium oxides, talcum, titanium dioxide, mono-, di- and tricalcium phosphate and cellulose polymers.
  • Suitable softeners or emulsifiers are tallow, hydrogenated tallow, hydrogen- ated or partly hydrogenated vegetable oils, cocoa butter, partial glycerides, lecithin, triacetin and saturated or unsaturated fatty acids containing 6 to 22 and preferably 12 to 18 carbon atoms and mixtures thereof.
  • Suitable dyes and Whiteners are, for example, the FD&C types, plant and fruit extracts permitted for colouring foods and titanium dioxide.
  • the gum bases may also contain waxes or may be wax-free
  • chewing gum preparations regu- larly contain a water-soluble component which is formed, for example, by softeners, sweeteners, fillers, flavours, flavour enhancers, emulsifiers, dyes, acidifiers, antioxidants and the like, with the proviso that the constituents have at least adequate solubility in water. Accordingly, individual constituents may belong both to the water- insoluble phase and to the water-soluble phase, depending on the water solubility of the special representatives. However, combinations may also be used, for example a combination of a water-soluble and a water-insoluble emulsifier, in which case the in- dividual representatives are present in different phases.
  • the water-insoluble compo- nent usually makes up 5 to 95% by weight and preferably 20 to 80% by weight of the preparation.
  • Water-soluble softeners or plasticizers are added to the chewing gum compo- sitions to improve chewability and the chewing feel and are present in the mixtures in quantities of typically 0.5 to 15% by weight.
  • Typical examples are glycerol, lecithin and aqueous solutions of sorbitol, hydrogenated starch hydrolysates or corn sirup.
  • Fillers are particularly suitable for the production of low-calorie chewing gums and may be selected, for example, from polydextrose, raftilose, raftilin, fructo-oligosac- charides (NutraFlora), palatinose oligosaccharides, guar gum hydrolyzates (Sun Fiber) and dextrins.
  • the chewing gums may additionally contain auxiliaries and additives which are suitable, for example, for dental care, more particularly for controlling plaque and gingivitis, such as for example chlorhexidine, CPC or triclosan. They may also contain pH adjusters (for example buffer or urea), anti-caries agents (for example phosphates or fluorides), biogenic agents (antibodies, enzymes, caffeine, plant extracts), providing these substances are permitted in foods and do not undesirably interact with one an- other.
  • auxiliaries and additives which are suitable, for example, for dental care, more particularly for controlling plaque and gingivitis, such as for example chlorhexidine, CPC or triclosan. They may also contain pH adjusters (for example buffer or urea), anti-caries agents (for example phosphates or fluorides), biogenic agents (antibodies, enzymes, caffeine, plant extracts), providing these substances are permitted in foods and do not undesirably interact with one an- other.
  • Toothpastes or tooth creams are generally understood to be paste-like prepa- rations of water, thickeners, humectants, abrasives or polishes, surfactants, sweeten- ers, flavorings, deodorizing agents and agents active against oral and dental diseases.
  • any of the usual polishes may be used, such as chalk, dicalcium phosphate, insoluble sodium metaphosphate, aluminium silicates, calcium pyrophosphate, finely particulate synthetic resins, silicas, aluminium oxide and aluminium oxide trihydrate.
  • polishes for toothpastes according to the invention are finely particulate xerogel silicas, hydrogel silicas, precipitated silicas, aluminium oxide trihydrate and finely particulate. alpha.-alumina, or mixtures of these polishes. Such polishes are preferably used in quantities of from about 15 to 40% by weight of the toothpaste.
  • Preferred humectants used for toothpastes according to the invention include low molecular weight polyethylene glycols, glycerol, sorbitol or mix- tures thereof in quantities of up to about 50% by weight of the toothpaste.
  • the thickening, finely particulate gel silicas and nonionic hydrocolloids such as hydroxy ethyl cellulose, hydroxy propyl guar, hydroxy ethyl starch, polyvinyl pyrrolidone, high molecular weight polyethylene glycol and vegetable gums, such as tragacanth, agaragar, carrageen moss, gum arabic and xanthan gum.
  • the desired fla- vor and aroma for preparations in accordance with the invention may be obtained by adding the components (a) and/or (b) and optionally also (c).
  • the oral preparations according to the invention may contain other standard aux- iliaries, such as dyes, preservatives and opacifiers, for example titanium dioxide.
  • aux- iliaries such as dyes, preservatives and opacifiers, for example titanium dioxide.
  • the oral compositions according to the invention may readily be com- bined with aqueous-alcoholic solutions containing different amounts of ethereal oils, emulsifiers, astringent and toning drug extracts, caries-inhibiting additives and flavour correctants.
  • the oral compositions of the present invention may include additional additives as for examples sweeteners or vitamins, in amounts of from about 0.1 to about 10 % b.w. These additives may also represent components of the respective medicaments.
  • Suitable sweet-tasting substances including natural sources of these sub- stances (component e5), such as for example sweet-tasting carbohydrates or sugars (e.g. sucrose (synonymous with saccharose), trehalose, lactose, maltose, melizitose, raffinose, palatinose, lactulose, D-fructose, D-glucose, D-galactose, L-rhamnose, D- sorbose, D-mannose, D-tagatose, D-arabinose, L-arabinose, D-ribose, D-glyceralde- hyde, maltodextrin) or vegetable preparations containing predominantly these carbo- hydrates (e.g.
  • sugar officinarum ssp. e.g. molasses, sugar syrups
  • sugar maple e.g.
  • agave agave thick juice
  • synthetic/enzymatic hy- drolysates of starch or sucrose e.g. invert sugar syrup, highly enriched fructose syrups made from corn starch
  • fruit concentrates e.g. from apples or pears, apple syrup, pear syrup
  • sugar alcohols e.g.
  • proteins e.g. miraculin, monellin, thaumatin, curculin, brazzein
  • sweeteners magap, sodiumcyclamate, acesulfame K, neohesperidin dihydrochal- cone, saccharin sodium salt, aspartame®, superaspartame, neotame, alitame, su- cralose, stevioside, rebaudioside, lugduname, carrelame, sucrononate, sucrooctate, monatin, phyllodulcin), certain sweet-tasting amino acids (glycine, D-leucine, D-threo- nine, D-asparagine, D-phenylalanine, D-tryptophan, L-
  • hernandulcin dihydrochalcone glycosides, glycyr- rhizin, glycyrrhetinic acid ammonium salt or other glycyrrhetinic acid derivatives), liq- uorice extracts (Glycyrrhizza glabra ssp.), Lippia dulcis extracts, Momordica ssp. ex- tracts or individual substances (in particular Momordica grosvenori [Luo Han Guo] and the mogrosides obtained therefrom), Hydrangea dulcis or Stevia ssp. (e.g. Stevia re- baudiana) extracts or individual substances.
  • the compositions may include vitamins (component e1 ).
  • Vitamins have diverse biochemical functions. Some have hormone-like functions as regulators of mineral metabolism (e.g., vitamin D), or regu- lators of cell and tissue growth and differentiation (e.g., some forms of vitamin A). Oth- ers function as antioxidants (e.g., vitamin E and sometimes vitamin C).
  • vitamins e.g. B complex vitamins
  • vitamins may be tightly bound to enzymes as part of prosthetic groups: For example, biotin is part of enzymes involved in making fatty acids.
  • Vitamins may also be less tightly bound to enzyme catalysts as coenzymes, detachable molecules that function to carry chemical groups or electrons between molecules.
  • folic acid carries various forms of carbon group - methyl, formyl, and methylene - in the cell.
  • suitable vitamins are selected from the group consisting of
  • Vitamin A retinol, retinal, beta carotene
  • Vitamin B1 (thiamine)
  • Vitamin B2 (riboflavin)
  • Vitamin B3 (niacin, niacinamide),
  • Vitamin B5 panthothenic acid
  • Vitamin B6 pyridoxine, pyridoxamine, paridoxal
  • Vitamin B7 (biotin)
  • Vitamin B9 folic acid, folinic acid
  • Vitamin B12 (cyanobalamin, hydoxycobalmin, methylcobalmin)
  • Vitamin C ascorbic acid
  • Vitamin D cholesterol
  • Vitamin E tocopherols, tocotrienols
  • Vitamin K (phyolloquinone, menaquinone).
  • the preferred vitamins are ascorbic acid and tocopherols. Said vitamins may be present in the food composition in amounts of about 0.1 to about 5 % b.w., and preferably about 0.5 to about 1 % b.w.
  • Food compositions according to the invention are any preparations or compo- sitions comprising the compositions according to the invention which are suitable for consumption and are used for nutrition or enjoyment purposes, and are generally prod- ucts which are intended to be introduced into the human or animal oral cavity, to remain there for a certain time and then either be eaten (e.g. ready-to-eat foodstuffs or feeds, see also herein below) or removed from the oral cavity again (e.g. chewing gums).
  • Such products include any substances or products which in the processed, partially processed or unprocessed state are to be ingested by humans or animals. They also include substances which are added to orally consumable products during their man- ufacture, preparation or treatment and which are intended to be introduced into the human or animal oral cavity.
  • the food compositions according to the invention also include substances which in the unchanged, treated or prepared state are to be swallowed by a human or animal and then digested; in this respect, the orally consumable products according to the invention also include casings, coatings or other encapsulations which are to be swallowed at the same time or which may be expected to be swallowed.
  • the expres- sion "orally consumable product” covers ready-to-eat foodstuffs and feeds, that is to say foodstuffs or feeds that are already complete in terms of the substances that are important for the taste.
  • the expressions "ready-to-eat foodstuff” and “ready-to-eat feed” also include drinks as well as solid or semi-solid ready-to-eat foodstuffs or feeds.
  • frozen products which must be thawed and heated to eating temperature before they are eaten.
  • Products such as yoghurt or ice- cream as well as chewing gums or hard caramels are also included among the ready- to-eat foodstuffs or feeds.
  • Preferred food compositions according to the invention also include “semi-fin- ished products”.
  • a semi-finished product is to be understood as being an orally consumable product which, because of a very high con- tent of flavourings and taste-imparting substances, is unsuitable for use as a ready-to- eat orally consumable product (in particular foodstuff or feed). Only by mixing with at least one further constituent (e.g. by reducing the concentration of the flavourings and taste-imparting substances in question) and optionally further process steps (e.g. heat- ing, freezing) is the semi-finished product converted into a ready-to-eat orally consum- able product (in particular foodstuff or feed). Examples of semi-finished products which may be mentioned here are
  • Food composition according to the invention preferably comprises one or more preparations for nutrition or enjoyment purposes.
  • these include in particular (reduced- calorie) baked goods (e.g. bread, dry biscuits, cakes, other baked articles), confection- ery (e.g. chocolates, chocolate bars, other products in bar form, fruit gums, dragées, hard and soft caramels, chewing gum), non-alcoholic drinks (e.g. cocoa, coffee, green tea, black tea, (green, black) tea drinks enriched with (green, black) tea extracts, rooi- bos tea, other herbal teas, fruit-containing soft drinks, isotonic drinks, refreshing drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks (e.g.
  • instant cocoa drinks, instant tea drinks, instant coffee drinks meat products (e.g. ham, fresh sausage or raw sausage preparations, spiced or marinated fresh or salt meat products), eggs or egg products (dried egg, egg white, egg yolk), cereal products (e.g. breakfast cereals, muesli bars, precooked ready-to-eat rice products), dairy prod- ucts (e.g. full-fat or reduced-fat or fat-free milk drinks, rice pudding, yoghurt, kefir, cream cheese, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, partially or completely hydrolysed milk-protein-containing products), products made from soy protein or other soybean fractions (e.g.
  • soy milk and products produced there- from drinks containing isolated or enzymatically treated soy protein, drinks containing soy flour, preparations containing soy lecithin, fermented products such as tofu or tempeh or products produced therefrom and mixtures with fruit preparations and op- tionally flavours), fruit preparations (e.g. jams, sorbets, fruit sauces, fruit fillings), veg- etable preparations (e.g. ketchup, sauces, dried vegetables, frozen vegetables, pre- cooked vegetables, boiled-down vegetables), snacks (e.g.
  • baked or fried potato crisps or potato dough products maize- or groundnut-based extrudates
  • fat- and oil-based products or emulsions thereof e.g. mayonnaise, remoulade, dressings, in each case full-fat or reduced-fat
  • other ready-made dishes and soups e.g. dried soups, instant soups, precooked soups
  • spices, spice mixtures and in particular seasonings which are used, for example, in the snacks field, sweetener preparations, tablets or sachets, other preparations for sweetening or whitening drinks or other foods.
  • the preparations within the scope of the invention can also be used in the form of semi-finished products for the production of further preparations for nutrition or enjoyment purposes.
  • the prep- arations within the scope of the invention can also be in the form of capsules, tablets (uncoated and coated tablets, e.g. enteric coatings), dragées, granules, pellets, solids mixtures, dispersions in liquid phases, in the form of emulsions, in the form of powders, in the form of solutions, in the form of pastes, or in the form of other preparations which can be swallowed or chewed, and in the form of food supplements.
  • tablets uncoated and coated tablets, e.g. enteric coatings
  • dragées granules, pellets, solids mixtures, dispersions in liquid phases, in the form of emulsions, in the form of powders, in the form of solutions, in the form of pastes, or in the form of other preparations which can be swallowed or chewed, and in the form of food supplements.
  • the preparations can also be in the form of capsules, tablets (uncoated and coated tablets, e.g. enteric coatings), dragées, granules, pellets, solids mixtures, dis- persions in liquid phases, in the form of emulsions, in the form of powders, in the form of solutions, in the form of pastes, or in the form of other preparations which can be swallowed or chewed, for example in the form of food supplements.
  • tablets uncoated and coated tablets, e.g. enteric coatings
  • dragées granules, pellets, solids mixtures, dis- persions in liquid phases, in the form of emulsions, in the form of powders, in the form of solutions, in the form of pastes, or in the form of other preparations which can be swallowed or chewed, for example in the form of food supplements.
  • the semi-finished products are generally used for the production of ready-to- use or ready-to-eat preparations for nutrition or enjoyment purposes.
  • Further constituents of a ready-to-eat preparation or semi-finished product for nutrition or enjoyment purposes can be conventional base substances, auxiliary sub- stances and additives for foods or enjoyment foods, for example water, mixtures of fresh or processed, vegetable or animal base or raw substances (e.g. raw, roast, dried, fermented, smoked and/or boiled meat, bone, cartilage, fish, vegetables, herbs, nuts, vegetable juices, vegetable pastes or mixtures thereof), digestible or non-digestible carbohydrates (e.g. sucrose, maltose, fructose, glucose, dextrins, amylose, amylopec- tin, inulin, xylans, cellulose, tagatose), sugar alcohols (e.g.
  • sorbitol, erythritol natural or hardened fats (e.g. tallow, lard, palm fat, cocoa fat, hardened vegetable fat), oils (e.g. sunflower oil, groundnut oil, maize germ oil, olive oil, fish oil, soya oil, sesame oil), fatty acids or their salts (e.g. potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (e.g. ⁇ -aminobutyric acid, taurine), peptides (e.g. glutathione), natural or processed proteins (e.g. gelatin), enzymes (e.g.
  • nucleic acids nucleotides
  • taste correctors for unpleasant taste impressions further taste modulators for further, generally not unpleasant taste impressions
  • other taste- modulating substances e.g. inositol phosphate, nucleotides such as guanosine mono- phosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid
  • emulsifiers e.g. lecithins, diacylglycerols, gum arabic
  • stabilisers e.g. carrageenan, alginate
  • preservatives e.g. benzoic acid and its salts, sorbic acid and its salts
  • antioxidants e.g.
  • tocopherol, ascorbic acid chelators
  • organic or inorganic acidifying agents e.g. acetic acid, phosphoric acid
  • Additional bitter substances e.g. quinine, caffeine, limonene, amarogentine, humu- lone, lupulone, catechols, tannins
  • substances that prevent enzymatic browning e.g. sulfite, ascorbic acid
  • ethereal oils e.g. sulfite, ascorbic acid
  • carotinoids flavonoids, anthocyans, chlorophyll and deriva- tives thereof
  • spices trigeminally active substances or plant extracts containing such trigeminally active substances, synthetic, natural or nature-identical flavourings or odorants as well as odour correctors.
  • Food compositions according to the invention for example those in the form of preparations or semi-finished products, preferably comprise a flavour composition in order to complete and refine the taste and/or odour.
  • a preparation can comprise as constituents a solid carrier and a flavour composition.
  • Suitable flavour compositions comprise, for example, synthetic, natural or nature-identical flavourings, odorants and taste-imparting substances, reaction flavourings, smoke flavourings or other flavour- giving preparations (e.g.
  • protein (partial) hydrolysates preferably protein (partial) hy- drolysates having a high arginine content, barbecue flavourings, plant extracts, spices, spice preparations, vegetables and/or vegetable preparations) as well as suitable aux- iliary substances and carriers.
  • flavour compositions or constituents thereof which produce a roasted, meaty (in particular chicken, fish, sea- food, beef, pork, lamb, mutton, goat), vegetable-like (in particular tomato, onion, garlic, celery, leek, mushroom, aubergine, seaweed), spicy (in particular black and white pep- per, cardamom, nutmeg, pimento, mustard and mustard products), fried, yeast-like, boiled, fatty, salty and/or pungent flavour impression and accordingly can enhance the spicy impression.
  • the flavour compositions generally comprise more than one of the mentioned ingredients.
  • compositions of the present invention are preferably selected from the group comprising
  • confectionery preferably reduced-calorie or calorie-free confectionery, preferably selected from the group comprising muesli bar products, fruit gums, dragées, hard caramels and chewing gum
  • non-alcoholic drinks preferably selected from the group comprising green tea, black tea, (green, black) tea drinks enriched with (green, black) tea extracts, rooi- bos tea, other herbal teas, fruit-containing low-sugar or sugar-free soft drinks, isotonic drinks, nectars, fruit and vegetable juices, fruit and vegetable juice prep- arations,
  • instant drinks preferably selected from the group comprising instant (green, black, rooibos, herbal) tea drinks,
  • cereal products preferably selected from the group comprising low-sugar and sugar-free breakfast cereals and muesli bars,
  • dairy products preferably selected from the group comprising reduced-fat and fat-free milk drinks, yoghurt, kefir, whey, buttermilk and ice-cream,
  • products made from soy protein or other soybean fractions preferably selected from the group comprising soy milk, products produced from soy milk, drinks con- taining isolated or enzymatically treated soy protein, drinks containing soy flour, preparations containing soy lecithin, products produced from preparations con- taining soy lecithin and mixtures with fruit preparations and optionally flavours,
  • sweeteners here denotes substances having a relative sweetening power of at least 25, based on the sweetening power of sucrose (which accordingly has a sweetening power of 1 ).
  • Sweeteners to be used in an orally consumable product (in particular foodstuff, feed or medicament) according to the invention (a) are prefer- ably non-cariogenic and/or have an energy content of not more than 5 kcal per gram of the orally consumable product.
  • Advantageous sweeteners in a preferred orally consumable product are selected from the following groups:
  • Naturally occurring sweeteners preferably selected from the group comprising miraculin, monellin, mabinlin, thaumatin, curculin, brazzein, pentaidin, D-phenyl- alanine, D-tryptophan, and extracts or fractions obtained from natural sources, comprising those amino acids and/or proteins, and the physiologically acceptable salts of those amino acids and/or proteins, in particular the sodium, potassium, calcium or ammonium salts, neohesperidin dihydrochalcone, naringin dihydro- chalcone, stevioside, steviolbioside, rebaudiosides, in particular rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, dulcosides and rubusoside, suavioside A, suavioside B, suavioside G, su
  • Synthetic sweet-tasting substances preferably selected from the group compris- ing magap, sodium cyclamate or other physiologically acceptable salts of cyclamic acid, acesulfame K or other physiologically acceptable salts of acesul- fame, neohesperidin dihydrochalcone, naringin dihydrochalcone, saccharin, sac- charin sodium salt, aspartame, superaspartame, neotame, alitame, advantame, perillartin, sucralose, lugduname, carrelame, sucrononate and sucrooctate.
  • synthetic sweet-tasting substances preferably selected from the group compris- ing magap, sodium cyclamate or other physiologically acceptable salts of cyclamic acid, acesulfame K or other physiologically acceptable salts of acesul- fame, neohesperidin dihydrochalcone, naringin dihydrochal
  • Advantageous thickeners in a preferred orally consumable product are selected from the group comprising: crosslinked polyacrylic acids and derivatives thereof, polysaccha- rides and derivatives thereof, such as xanthan gum, agar-agar, alginates or tyloses, cellulose derivatives, for example carboxymethylcellulose or hydroxycarboxymethyl- cellulose, fatty alcohols, monoglycerides and fatty acids, polyvinyl alcohol and polyvi- nylpyrrolidone.
  • an orally consumable product in particular foodstuff or feed
  • milk thickened with lactic acid bacteria and/or cream thickened with lactic acid bacteria which preferably is selected from the group comprising yoghurt, kefir and quark.
  • a food composition according to the invention comprising milk thickened with lactic acid bacteria and/or cream thickened with lactic acid bacteria is advantageously an orally consumable product which comprises a probiotic, wherein the probiotic is preferably selected from the group comprising Bifidobacterium animalis subsp. lactis BB-12, Bifidobacterium animalis subsp. lactis DN-173 010, Bifidobacterium animalis subsp.
  • lactis HN019 Lactobacillus acidophilus LA5, Lactobacillus acidophilus NCFM, Lactobacillus johnsonii La1 , Lactobacillus casei immunitass/defensis, Lactobacillus ca- sei Shirota (DSM 20312), Lactobacillus casei CRL431 , Lactobacillus reuteri (ATCC 55730) and Lactobacillus rhamnosus (ATCC 53013).
  • an orally consumable product in particular foodstuff, feed or medicament
  • a chewing gum that is a chewing gum and comprises a chewing-gum base.
  • the chewing-gum base is preferably selected from the group comprising chewing-gum or bubble-gum bases. The latter are softer, so that gum bubbles can also be formed therewith.
  • Preferred chewing-gum bases according to the invention include, in Addition to the natural resins or the natural latex chicle that are traditionally used, elastomers such as polyvinyl acetate (PVA), polyethylene, (low or medium molecular weight) polyisobutene (PIB), polybutadiene, isobutene-isoprene copolymers (butyl rubber), polyvinyethyl ether (PVE), polyvinylbutyl ether, copolymers of vinyl esters and vinyl ethers, styrene-butadiene copolymers (styrene-butadiene rub- ber, SBR) or vinyl elastomers, for example based on vinyl acetate/vinyl laurate, vinyl acetate/vinyl stearate or ethylene/vinyl acetate, as well as mixtures of the mentioned elastomers, as described, for example, in EP 0 242 325, US 4,518,
  • chewing-gum bases that are preferably to be used according to the invention preferably comprise further con- stituents such as, for example, (mineral) fillers, plasticisers, emulsifiers, antioxidants, waxes, fats or fatty oils, such as, for example, hardened (hydrogenated) vegetable or animal fats, mono-, di- or tri-glycerides.
  • suitable (mineral) fillers are, for example, cal- cium carbonate, titanium dioxide, silicon dioxide, talcum, aluminum oxide, dicalcium phosphate, tricalcium phosphate, magnesium hydroxide and mixtures thereof.
  • Suitable plasticisers, or agents for preventing adhesion are, for example, lanolin, stearic acid, sodium stearate, ethyl acetate, diacetin (glycerol diacetate), triacetin (glyc- erol triacetate), triethyl citrate.
  • Suitable waxes are, for example, paraffin waxes, can- delilla wax, carnauba wax, microcrystalline waxes and polyethylene waxes.
  • Suitable emulsifiers are, for example, phosphatides such as lecithin, mono- and di-glycerides of fatty acids, for example glycerol monostearate.
  • Chewing gums according to the invention preferably comprise constituents such as sugars of different types, sugar substitutes, other sweet-tasting substances, sugar alcohols (in particular sorbitol, xylitol, mannitol), ingredients having a cooling effect, taste correctors for unpleasant taste impressions, further taste-modulating substances (e.g.
  • inositol phosphate nucleotides such as gua- nosine monophosphate, adenosine monophosphate or other substances such as so- dium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers, sta- bilisers, odour correctors and flavours (e.g. eucalyptus-menthol, cherry, strawberry, grapefruit, vanilla, banana, citrus, peach, blackcurrant, tropical fruits, ginger, coffee, cinnamon, combinations (of the mentioned flavours) with mint flavours as well as spearmint and peppermint on their own).
  • flavours e.g. eucalyptus-menthol, cherry, strawberry, grapefruit, vanilla, banana, citrus, peach, blackcurrant, tropical fruits, ginger, coffee, cinnamon, combinations (of the mentioned flavours) with mint flavours as well as spearmint and peppermint on their own.
  • flavours e.g. eucalyptus-
  • Another object of the present invention refers to a method for
  • compositions are added in amounts of from 0.01 to 2 wt.-percent and preferably from about 0.1 to 1 wt.-percent - calculated on the preparations.
  • compositions according to the present invention are also claimed.
  • composition 1 stands for any mixture of the preferred compounds (a) as cited in section [0037] with one of the compounds (b) to (d) or their mixtures.
  • Cosmetic lotion for body wash (Amounts in % b.w.)
  • Cosmetic lotion for body wash with Triclosan (Amounts in % b.w.)
  • Intimate wash (Amounts in % b.w.)
  • Liquid soap (Amounts in % b.w.)
  • Anti-dandruff Shampoo (Amounts in % b.w.)
  • Sprayable hair conditioner with zinc pyrithrione. leave-on (Amounts in % b.w.)
  • Shaving foam (Amounts in % b.w.)
  • Zirconium suspensoid antiperspirant stick (Amounts in % b.w.)
  • Antiperspirant formulations (Amounts in % b.w.)
  • O/W lotion (Amounts in % b.w.)
  • Cream (Amounts in % b.w.)
  • Moisturizing body care cream (Amounts in % b.w.)
  • Anti-wrinkle cream (Amounts in % b.w.)
  • Moisturizing and disinfecting face mask (Amounts in % b.w.)
  • Sprayable disinfecting gel (Amounts in % b.w.)
  • Anti-acne wash (Amounts in % b.w.)
  • Cosmetic sun protection composition (Amounts in % b.w.)
  • Sun protection milk (W/O) (Amounts in % b.w.)
  • Silicone emulsion (Amounts in % b.w.)
  • Air freshener in gel form (Amounts in % b.w.)
  • Liquid detergent (Amounts in % b.w.)
  • Liquid detergent concentrate (Amounts in % b.w.) Table F53
  • Dish washing concentrate (Amounts in % b.w.)
  • Dish washing concentrate (Amounts in % b.w.)
  • Tooth paste all amounts in % b.w. Table F59
  • Mouth wash concentrate all amounts in % b.w. Table F60

Abstract

Suggested are compositions comprising benzoisoxazole derivatives on one hand and physiological cooling or warming agents, flavors and/or fragrances on the other for masking, enhancing and/or boosting flavors and improving antimicrobial stability and soothing behaviour of consumer products comprising them.

Description

COMPOSITIONS COMPRISING TRPM8 AGONISTIC COOLING AGENTS
AREA OF INVENTION
[0001] The present invention refers to the area of preservation and concerns new com- position comprising specific multi-purpose mixtures with anti-microbial activity, flavor boosting activity, flavor masking activity and soothing activity.
BACKGROUND OF THE INVENTION
[0002] Cosmetic products are generally manufactured under sterile conditions to pre- vent contamination. In the case of foodstuffs, the requirements are even more strin- gent; dairy products, for example, must be subjected to high-temperature heating ("pasteurization") before they can be marketed at all.
[0003] However, in the course of their use, the above-mentioned products are regularly contaminated and chemically altered by microorganisms, especially bacteria and fungi, so that they are subsequently no longer usable or edible, but on the contrary represent a danger to healthy organisms. This can happen through the spatula, which has a contamination and then transfers it to the cream, or bacteria are simply transferred through the air.
[0004] Even though there is a growing market for products that are untreated and do not contain substances that kill microorganisms, there is just as much interest in prod- ucts that have a sufficiently long shelf life after the package is broken open. For this reason, preservatives are added to cosmetics and food products. By their very nature, preservatives are generally considered to be hazardous for contact with human skin and especially mucous membranes, because a chemical that is capable of killing mi- croorganisms is always suspected of triggering harmful processes in the human or- ganism. The list of approved preservatives is therefore shrinking from year to year at the same rate as critical studies are revealing dangers for previously common sub- stances.
[0005] Apart from new preservatives that are as natural as possible, which still need to be developed, there is great interest in both the cosmetics and food industries in ways of reducing the concentration of preservatives in a formulation without sacrificing pro- tection against microbial attack. A first concept is to use synergistic mixtures of different preservatives. Another approach pursues the possibility of identifying multifunctional substances or mixtures of substances that, in Addition to their primary properties, are also antimicrobially active, at least to a small extent. To the extent that these sub- stances contribute to the antimicrobial properties of a formulation, the amount of actual preservative can be reduced.
[0006] Another widespread problem, both in the field of cosmetics and cleaning prod- ucts and in foodstuffs, is to mask the unpleasant odor or taste of ingredients that cannot be replaced in the formulation. A typical example is fluorine compounds used in dental care products. There is also a constant need for substances that perform important tasks in the above-mentioned preparations, such as for example providing a physio- logical cooling effect on the skin or mucous membrane, while also exhibiting other properties that are important for the formulation. Special interest is shown in prepara- tions which, preferably even in very small quantities, are capable of intensifying posi- tive taste or odor impressions or of bringing them to bear in the first place.
RELEVANT PRIOR ART
[0007] Benzisoxazoles are known molecules which are used as psychopharmaca for fighting various diseases.
[0008] For example US 5,668,154 A (HOECHST) refers to novel pyridiniminyl-1 ,2-ben- zisoxazoles and -benzisothiazoles, intermediates and processes for the preparation thereof, and methods of relieving memory dysfunction and treating depression. US 5,114,936 A (HOECHST) discloses 6,7-dihydro-3-phenyl-1 ,2-benzisoxazol-4(5H)- ones and -ols as as antipsychotic and analgesic agents, while US 5,055,476 A (HOECHST) suggest 3-(1 ,2-Benzisoxazol-3-yl)-4-pyridinamines and derivatives as an- algesics, for alleviating various memory dysfunctions characterized by a decreased cholinergic function, as cognition enhancers in the treatment of senile dementia such as Alzheimer's disease and as topical antiinflammatory agents for the treatment of var- ious dermatoses.
[0009] ES 2006887 A and ES 2006888 A (JANSSEN) refer to 3-Piperidinyl 1 ,2-benzo- isoxazoles and relate to their anti-psychotic and anti-serotonin activity
[0010] JP 9 268 188 A2 (MEIJI) relates to 1 -benzoyl-3[2-[4-(6-fluoro-1 ,2- benzoisoxa- zol-3-yl)-1 -piperidinyl]ethyl]perhydrobenzoimidazol-2-one} which is useful as a psy- chotropic agent such as an antischizophrenic, an antianxiety agent, or an antidepres- sant.
[0011] US 2005 026922 AA and US 2007 270430 AA (PFIZER) concern ami- nomethylpyridyloxymethyl/benzisoxazole substituted azabicyclic compounds, a phar- maceutical composition comprising same, and a method of treating a cognitive disor- der selected from the group consisting of Asperger's disorder, Autistic Disorder, Oppo- sitional Defiant Disorder, and Conduct Disorder.
[0012] WO 2021 102896 A1 and WO 2021 105261 A1 (GIVAUDAN) disclose benzo- isoxazole derivatives and a method for modulating TRPV receptors by bringing them into contact with said derivatives.
[0013] Similar structures and their potential as TRPV modulators are disclosed in the following papers:
• LIU Y ET AL “Amino acid derived intramolecular 1,3-dipolar cycloAdditions that form bridged medium ring systems with diastereoiselective control”, TETRAHE- DRON 58(16), p3159-3170 (2002); • BANUCCI LEBEL ET AL “Intramolecular nitrone-olefin cycloAdditions”, J. ORG.CHEM. 36(17), p2440-2448 (1971);
• NORMAN A LEBEL ET AL “The Addition of nitrones to olefins”, J.AM.CHEM.SOC. 86(18), p3759-3767 (1964);
• BRION F ET AL “Stereoselective synthesis of a trans-octahydroindole derivative”, TETRAHEDRON Vol 33(34), p4889-4892 (1992);
• KALEVI PILHAJA ET AL “Conformitional analysis 30-A’H and 13C NMR stereochemical study on N-methyl-substituted cis- and trans-fused Octahydro-2H- 1,3- and -3, 1 -benzoxazines”, MAGNETIC RESONANCE IN CHEMISTRY, 34, P998-1002 (1996);
• P SOH I R ET AL “Steroechemical studies-XIV: cyclic amino alcohols and related compounds VII”, ORGANIC MAGNETIC RESONANCE 5(3), p159-160 (1973);
• FISYUK A S ET AL “Interaction of methyl-N-(3-oxoalkyl)carbamates” CHEMIS- TRY OF HETEROCYCLIC COMPOUNDS 37, p597-609 (2001).
OBJECT OF THE INVENTION
[0014] Therefore, it has been the object of the present invention providing compositions which are commonly used in cosmetic products or foodstuffs and which Additionally possess appreciable antimicrobial properties, so that their use can reduce the amount of preservative otherwise required for antimicrobial finishing , mask unpleasant flavors, particularly unpleasant flavors of fluorine derivatives and bitter compounds; and/or en- hance and/or boost the performance of a flavor, a physiological cooling/warming agent, a sweetener or a soothing agent.
BRIEF DESCRIPTION OF THE INVENTION
[0015] A first object of the present invention refers to a composition comprising or con- sisting of
(a) at least one benzoisoxazole derivative according to formula (I), a salt or a solvate thereof,
Figure imgf000004_0001
wherein - X is O and the dotted line represents a single bond; or - X is selected from CR 3 and NR 3, - wherein R3 is selected from hydrogen, C1-C6 alkyl, C1-C alkyl substituted with one or two OH groups, C3-C7 cycloalkyl, C3-C7 cycloalkyl substituted with one or two OH groups, C5-C7 cycloalkenyl, C5-C7 cycloalkenyl substi- tuted with one, two or three C1-C3 alkyl groups, and phenyl, and the dotted line represents a single bond or a double bond; - R1 is selected from hydrogen, - C1-C6 alkyl, - C1-C7 alkyl substituted with one or two OH groups, - C3-C7 alkenyl, - phenyl optionally substituted with up to five (e.g. one, two or three) substit- uents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C 1-C 6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C 3-C7 cycloalkyl, -C (O) O- R10 wherein R10 is selected from hydrogen and C 1-C 3 alkyl, and - SR11 wherein R11 is selected from hydrogen and C1-C3 alkyl (including ethyl and isopropyl), - naphtyl optionally substituted with up to five (e.g. one, two or three) substit- uents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C (O) O- R10 wherein R10 is selected from hydrogen and C1-C3 alkyl, and - SR 11 wherein R11 is selected from hydrogen and C1-C3 alkyl (including ethyl and isopropyl), and - C5-C10 mono-or bicyclic aryl wherein 1 or 2 C-atoms are replaced by a het- ero atom independently selected from sulfur, nitrogen, and oxygen, option- ally substituted with up to three (e.g. 1 or 2) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1- C6 alkyloxy, C 1-C 6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is selected from hydrogen and C1-C6 alkyl, and -SR11 wherein R11 is selected from hydro- gen and C1-C3 alkyl (including ethyl and isopropyl); - R2, R4, R5, and R7 are independently selected from hydrogen and C1-C6 al- kyl; - R6 is selected from hydrogen, C1-C6 alkyl (e.g. ethyl, isopropyl), and C3- C7 cycloalkyl; - R8 and R9 are independently selected from hydrogen, and C1-C6 alkyl, or - R8 and R9 form together with the C-atom to which they are attached a 3, 4, 5, 6, or 7-membered cycloalkyl ring; and - n is 0, or n is 1 and R’ is selected from hydrogen, C1-C6 alkyl, C2-C6 alkyl substituted with one or two OH groups, C2-C6 alkenyl, or R’ forms together with the C-atom to which it is attached a carbonyl group (C=O);
(b) at least one physiological cooling or warming agent and/or
(c) at least one aroma or flavoring compound, and/or
(d) at least one fragrance whereby the compounds are present in a ratio by weight (a):(b+c+d) from about 1 :1 ,500,00 to about 1 :1 , preferably from 1 :500,000 to about 1 :10. More preferably from about 1 :100,000 to about 1 :100, and most preferably from about 1 :40,000 to about 1 :500.
[0016] In a first embodiment the compositions according to the present invention in- clude compound (a) and one additional additive, namely compound (b), compound (c) or compound (d). However, it is also possible having compositions with three or four components. For ternary mixtures the preferred ratios by weight (b):(c), (b):(d) or (c):(d) are from about 10:90 to about 90:10 and preferably from about 25:75 to about 75:25. For quaternary mixtures the preferred ratios by weight (b):(c):(d) are from about 30:30:40 to about 40:30:30.
[0017] Surprisingly, it was found that defined mixtures of representatives of substance class (a) with physiological cooling or warming substances, flavors and/or fragrances, possess moderate antimicrobial activity against the most important germs found in both cosmetic products and foods. If these mixtures are used, on the one hand they fulfill their actual task, namely, for example, to produce a cooling effect on the skin or to impart a certain flavor or fragrance to a particular product, but at the same time they also contribute to the antimicrobial stabilization of the products, so that the amount of preservatives actually required can be reduced. These findings are therefore particu- larly unexpected, since the substances tested alone do not possess any antimicrobial activity. At this point, therefore, a synergy can also be observed. Moreover they pos- sess the ability to mask unpleasant flavors, particularly unpleasant flavors of fluorine derivatives and bitter compounds; and/or enhance and/or boost the performance of a flavor, a sweetener or a soothing agent.
BENZOISOXAZOLE DERIVATIVES
[0018] Benzoisoxazole derivatives forming group (a) belong to the group of TRMP8 modulators. The structures and their synthesis are known from WO 2021 102896 A1 and WO 2021 105261 A1 which are hereby incorporated by reference.
[0019] Non-limiting examples are compounds of formula (I), a salt or solvate thereof, wherein X is CR3 wherein R3 is selected from hydrogen, C1-C6 alkyl, C1-C7 alkyl sub- stituted with one or two OH groups, C3-C cycloalkyl, C3-C7 cycloalkyl substituted with one or two OH groups, C5-C7 cycloalkenyl, C5-C ycloalkenyl substituted with one, two or three C1-C3 alkyl groups, and phenyl; and the dotted line represents a single bond or a double bond;
[0020] Further non-limiting examples are compound of formula (I), a salt or solvate thereof, wherein X is CR3 wherein R3 is selected from hydrogen, C1-C6 alkyl, C1-C7 al- kyl substituted with one or two OH groups, C3-C7 cycloalkyl, C3-C7 cycloalkyl substi- tuted with one or two OH groups, C5-C7 cycloalkenyl, C5-C7 cycloalkenyl substituted with one, two or three C1-C3 alkyl groups, and phenyl; and the dotted line represents a single bond; and n is 0.
[0021] Further non-limiting examples are compound of formula (I), a salt or solvate thereof, wherein X is NR3, wherein R3 is selected from hydrogen, C1-C6 alkyl, C1-C7 al- kyl substituted with one or two OH groups, C3-C7 cycloalkyl, C3-C7 cycloalkyl substi- tuted with one or two OH groups, C5-C7 cycloalkenyl, C5-C7 cycloalkenyl substituted with one, two or three C1-C3 alkyl groups, and phenyl; and the dotted line represents a single bond or a double bond;
[0022] Further non-limiting examples are compound of formula (I), a salt or solvate thereof, wherein X is NR3, wherein R3 is selected from hydrogen, C1-C6 alkyl, C1-C7 al- kyl substituted with one or two OH groups, C3-C7 cycloalkyl, C3-C7 cycloalkyl substi- tuted with one or two OH groups, C5-C7 cycloalkenyl, C5-C7 cycloalkenyl substituted with one, two or three C1-C3 alkyl groups, and phenyl; the dotted line represents a single bond; and n is 0.
[0023] Further non-limiting examples are compound of formula (I), a salt or solvate thereof, wherein X is CR3, wherein R3 is selected from hydrogen, C1-C6 alkyl, C1-C7 al- kyl substituted with one or two OH groups, C3-C7 cycloalkyl, C3-C7 cycloalkyl substi- tuted with one or two OH groups, C5-C7 cycloalkenyl, C5-C cycloalkenyl substituted with one, two or three C1-C3 alkyl groups, and phenyl; and the dotted line represents a single bond; n is 0; and R1 is phenyl optionally substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (in- cluding Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is selected from hy- drogen and C 1-C 3 alkyl, and -SR11 wherein R11 is selected from hydrogen and C1- C3 alkyl (including ethyl and isopropyl).
Preferred structure (la)
[0024] Further, non-limiting examples are compounds of formula (la), a salt or solvate thereof,
Figure imgf000008_0001
wherein - X is selected C and N; - R3 is selected from hydrogen, C1-C6 alkyl, C1-C7 alkyl substituted with one or two OH groups, C3-C7 cycloalkyl, C3-C7 cycloalkyl substituted with one or two OH groups, C5-C7 cycloalkenyl, C5-C7 cycloalkenyl substituted with one, two or three C1-C3 alkyl groups, and phenyl; - R1 is selected from hydrogen, - C1-C6 alkyl, - C1-C7 alkyl substituted with one or two OH groups, - C3-C7 alkenyl, - phenyl optionally substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is selected from hydro- gen and C1-C3 alkyl, and -SR11 wherein R11 is selected from hydrogen and C1- 3 alkyl (including ethyl and isopropyl), naphtyl optionally substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is selected from hydro- gen and C1-C3 alkyl, and -SR11 wherein R11 is selected from hydrogen and C1- C3 alkyl (including ethyl and isopropyl), and
C5-C10 mono-or bicyclic aryl wherein 1 or 2 C-atoms are replaced by a hetero atom independently selected from sulfur, nitrogen, and oxygen, optionally substi- tuted with up to three (e.g. 1 or 2) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl compris- ing up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, - C(O)O-R10 wherein R10 is selected from hydrogen and C1-C3 alkyl, and - SR11 wherein R11 is selected from hydrogen and C 1-C 3 alkyl (including ethyl and isopropyl); - R2, R4, R5, and R7 are independently selected from hydrogen and C1-C6 alkyl; - R6 is selected from hydrogen, C1-C6 alkyl (e.g. ethyl, isopropy), and C3-C7 cyclo- alkyl; - R8 and R9 are independently selected from hydrogen, and C1-C6 alkyl, or - R8 and R9 form together with the C-atom to which they are attached a 3, 4, 5, 6, or 7-membered cycloalkyl ring.
[0025] Further non-limiting examples are compounds of formula (la), a salt or solvate thereof, wherein X is C; and R3 is selected from hydrogen, C1-C6 alkyl, C1-C7 alkyl sub- stituted with one or two OH groups, C3-C7 cycloalkyl, C3-C7 cycloalkyl substituted with one or two OH groups, C5-C7 cycloalkenyl, C5-C7 cycloalkenyl substituted with one, two or three C1-C3 alkyl groups, and phenyl.
[0026] Further non-limiting examples are compound of formula (la), a salt or solvate thereof, wherein X is C; - R1 is selected from hydrogen, - C1-C6 alkyl, - C1-C7 alkyl substituted with one or two OH groups, - C3-C7 alkenyl, - phenyl optionally substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is selected from hydro- gen and C1-C3 alkyl, and -SR11 wherein R11 is selected from hydrogen and C1- C3 alkyl (including ethyl and isopropyl), - naphtyl optionally substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is selected from hydro- gen and C1-C3 alkyl, and -SR11 wherein R11 is selected from hydrogen and C1- C3 alkyl (including ethyl and isopropyl), and - C5-C10 mono-or bicyclic aryl wherein 1 or 2 C-atoms are replaced by a hetero atom independently selected from sulfur, nitrogen, and oxygen, optionally substi- tuted with up to three (e.g. 1 or 2) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl compris- ing up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, - C(O)O-R10 wherein R10 is selected from hydrogen and C1-C3 alkyl, and - SR11 wherein R11 is selected from hydrogen and C 1-C 3 alkyl (including ethyl and isopropyl); - R2, R4, and R5 are independently selected from hydrogen and C 1-C 6 alkyl; - R3 is hydrogen; - R6 is selected from hydrogen, C1-C6 alkyl (e.g. ethyl, isopropy), and C3-C7 cyclo- alkyl; - R7 is hydrogen; - R8 and R9 are independently selected from hydrogen, and C1-C6 alkyl, or - R8 and R9 form together with the C-atom to which they are attached a 3, 4, 5, 6, or 7-membered cycloalkyl ring.
[0027] Further non-limiting examples are compound of formula (la), a salt or solvate thereof, wherein X is C, and R3 is hydrogen; and R1 is selected from phenyl optionally substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl com- prising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O- R10 wherein R10 is selected from hydrogen and C1- 3 alkyl, and -SR11 wherein R11 is selected from hydrogen and C1-C3 alkyl (including ethyl and isopropyl).
[0028] Further non-limiting examples are compound of formula (la), a salt or solvate thereof, wherein X is C; R1 is selected from phenyl optionally substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1- 6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 hal- ogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is se- lected from hydrogen and C1-C3 alkyl, and -SR11 wherein R11 is selected from hydro- gen and C1-C3 alkyl (including ethyl and isopropyl); R3 is hydrogen; and R7 is hydro- gen.
[0029] Further non-limiting examples are compound of formula (la), a salt or solvate thereof, wherein X is C; R1 is selected from phenyl optionally substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, N 2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 hal- ogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is se- lected from hydrogen and C1-C3 alkyl, and -SR11 wherein R 1 is selected from hydro- gen and C1- 3 alkyl (including ethyl and isopropyl); R3 is hydrogen; R4 is hydrogen, R5 is C1-C3 alkyl; and R7 is hydrogen.
Preferred structure (lb) [0030] In one particular embodiment the compounds of formula (la) wherein X is C, are compound of formula (lb) have the relative stereochemistry as depicted
Figure imgf000011_0001
wherein - R1 is selected from hydrogen, - C1-C6 alkyl, - C1-C7 alkyl substituted with one or two OH groups, - C3-C7 alkenyl, - phenyl optionally substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is selected from hydro- gen and C1-C3 alkyl, and -SR11 wherein R11 is selected from hydrogen and C1- C3 alkyl (including ethyl and isopropyl), - naphtyl optionally substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is selected from hydro- gen and C 1-C 3 alkyl, and -SR 11 wherein R11 is selected from hydrogen and C1- C3 alkyl (including ethyl and isopropyl), and - C5-C10 mono-or bicyclic aryl wherein 1 or 2 C-atoms are replaced by a hetero atom independently selected from sulfur, nitrogen, and oxygen, optionally substi- tuted with up to three (e.g. 1 or 2) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl compris- ing up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C 3-C7 cycloalkyl, - C(O)O-R10 wherein R10 is selected from hydrogen and C 1-C 3 alkyl, and - SR11 wherein R11 is selected from hydrogen and C1-C3 alkyl (including ethyl and isopropyl); - R3 is selected from hydrogen, C1-C6 alkyl, C1-C7 alkyl substituted with one or two OH groups, C3-C7 cycloalkyl, C3-C7 cycloalkyl substituted with one or two OH groups, C5-C7 cycloalkenyl, C5-C7 cycloalkenyl substituted with one, two or three C1-C3 alkyl groups, and phenyl; - R2, R4, R5, and R7 are independently selected from hydrogen and C1-C6 alkyl; - R6 is selected from hydrogen, C1-C6 alkyl (e.g. ethyl, isopropy), and C3-C7 cyclo- alkyl; - R8 and R9 are independently selected from hydrogen, and C1-C6 alkyl, or - R8 and R9 form together with the C-atom to which they are attached a 3, 4, 5, 6, or 7-membered cycloalkyl ring.
[0031] Further non-limiting examples are compound of formula (lb), a salt or solvate thereof, wherein X is C; R1 is selected from phenyl and phenyl substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 hal- ogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is se- lected from hydrogen and C1-C3 alkyl, and -SR11 wherein R11 is selected from hydro- gen and C1- 3 alkyl (including ethyl and isopropyl); and R3 is hydrogen.
[0032] Further non-limiting examples are compound of formula (lb), a salt or solvate thereof, wherein X is C; R 1 is selected from phenyl optionally substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1- 6 alkyloxy comprising up to 5 halo- gen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is se- lected from hydrogen and C1-C3 alkyl, and -SR11 wherein R11 is selected from hydro- gen and C1-C3 alkyl (including ethyl and isopropyl); R3 is hydrogen; and R7 is hydro- gen.
[0033] Further non-limiting examples are compound of formula (lb), a salt or solvate thereof, wherein X is C; R1 is selected from phenyl optionally substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1- 6 alkyloxy comprising up to 5 halo- gen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is se- lected from hydrogen and C1-C3 alkyl, and -SR11 wherein R11 is selected from hydro- gen and C1-C3 alkyl (including ethyl and isopropyl); R3 is hydrogen; R4 is hydrogen, R5 is C1-C3 alkyl; and R7 is hydrogen.
[0034] Further non-limiting examples are compound of formula (lb), a salt or solvate thereof, wherein R3 and R7 are both hydrogen, and R8 and R9 are both methyl.
[0035] Further non-limiting examples are compound of formula (lb), a salt or solvate thereof, wherein X is C, R1 is selected from phenyl and phenyl substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 hal- ogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is se- lected from hydrogen and C1-C3 alkyl, and -SR11 wherein R11 is selected from hydro- gen and C1-C3 alkyl (including ethyl and isopropyl); R3 and R7 are both hydrogen; and R8 and R9 are both methyl.
[0036] Further non-limiting examples are compound of formula (lb), a salt or solvate thereof, wherein X is C, R1 is selected from phenyl and phenyl substituted with up to five (e.g. one, two or three) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 hal- ogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is se- lected from hydrogen and C1-C3 alkyl, and -SR11 wherein R11 is selected from hydro- gen and C1-C3 alkyl (including ethyl and isopropyl); R3 and R7 are both hydrogen; R6 is methyl or isopropy; and R8 and R9 are both methyl.
[0037] Further non-limiting examples are compound of formula (I), (la) and (lb) wherein R1 is selected from C1-C6 alkyl, C1-C7 alkyl substituted with one or two OH groups, and C3-C7 alkenyl.
[0038] Further non-limiting examples are compound of formula (I), (la) and (lb) wherein R1 is selected from C1-C6 alkyl, C1-C7 alkyl substituted with one or two OH groups, and C3-C7 alkenyl; R2 is hydrogen or methyl; and R8 and R9 are methyl.
[0039] Further non-limiting examples are compound of formula (I), (la) and (lb) wherein R1 is selected from C1-C6 alkyl, C1-C7 alkyl substituted with one or two OH groups, and C3-C7 alkenyl; R2 is hydrogen or methyl; R4 is hydrogen, R5 is C1-C3 alkyl; and R8 and R9 are methyl.
[0040] Further non-limiting examples are compound of formula (I), (la) and (lb) wherein R1 is selected from C1-C6 alkyl, C1-C7 alkyl substituted with one or two OH groups, and C3-C 7 alkenyl; R is hydrogen or methyl; R4 is hydrogen, R5 is C1- 3 alkyl; R6 is methyl or isopropyl; and R8 and R9 are methyl.
Preferred structures
[0041] Further non-limiting exmples are compounds of formula (I), (la) or (lb) selected from the group consisting of:
• 1 , 3, 3, 5, 7-pentamethyl-5- (3-methylbut-2-en-1 -yl) octahydrobenzo [c] isoxa- zole;
• 1 , 3, 3, 5, 7-pentamethyl-5- (4-methylpyridin-3-yl) octahydrobenzo [c] isoxazole;
• 1 , 3, 3, 5, 7-pentamethyl-5- (pyridin-3-yl) octahydrobenzo [c] isoxazole;
• 1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazole;
• 1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazole hydrochloride; • 1 , 3, 3, 6-tetramethyloctahydrobenzo [c] isoxazole;
• 1 , 3, 3-trimethyl-6- ((R) -4-methylcyclohex-3-en-1 -yl) octahydrobenzo [c] isoxa- zole;
• 1 , 5, 7-trimethylhexahydro-1 H-spiro [benzo [c] isoxazole-3, 1 '-cyclopentane];
• 1-ethyl-3, 3, 5, 7-tetramethyl-5- (3-methylbut-2-en-1 -yl) octahydrobenzo [c] isoxazole;
• 1-isopropyl-3, 3, 5, 7-tetramethyl-5- (3-methylbut-2-en-1 -yl) octahydrobenzo [c] isoxazole;
• 1-isopropyl-3, 3, 5, 7-tetramethyloctahydrobenzo [c] isoxazol-1 -ium chloride;
• 1-isopropyl-3, 3, 5, 7-tetramethyloctahydrobenzo [c] isoxazole;
• 1-isopropyl-5, 7-dimethylhexahydro-1 H-spiro [benzo [c] isoxazole-3, 1 '-cyclo- pentane];
• 2- (1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
• 2-methyl-3- (1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzo- nitrile;
• 5- (2, 4-dimethoxyphenyl) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxa- zole;
• 5- (2, 5-dimethoxyphenyl) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxa- zole;
• 5- (6-methoxypyridin-2-yl) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxa- zole;
• 5, 7-diethyl- 1 , 3, 3-trimethyloctahydrobenzo [c] isoxazole;
• 5-ethyl-1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazole;
• 6-isopentyl-1 , 4, 4, 8-tetramethyloctahydro-2H-benzo [d] [1 , 3] oxazin-2-one;
• 6-isopentyl-1 , 4, 4, 8-tetramethyloctahydro-2H-benzo [d] [1 , 3] oxazine;
• rac-(3aR, 5R, 7aR) -1 , 3, 3-trimethyl-5-pentyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7aR) -1 , 3, 3-trimethyl-5-propyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7aR) -1 -ethyl-3, 3-dimethyl-5-propyloctahydrobenzo [c] isoxa- zole;
• rac-(3aR, 5R, 7aR) -1 -isopropyl-3, 3-dimethyl-5-propyloctahydrobenzo [c] isox- azole;
• rac-(3aR, 5R, 7aR) -5-butyl-1 , 3, 3-trimethyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7aR) -5-butyl-1 -ethyl-3, 3-dimethyloctahydrobenzo [c] isoxazole; • rac-(3aR, 5R, 7aR) -5-butyl-1 -isopropyl-3, 3-dimethyloctahydrobenzo [c] isoxa- zole;
• rac-(3aR, 5R, 7aR) -5-ethyl-1 -isopropyl-3, 3-dimethyloctahydrobenzo [c] isoxa- zole;
• rac-(3aR, 5R, 7R, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (2- (methylthio) phenyl) - octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7R, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyl-5- (3-methylbut-2-en-1 -yl) octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7R, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyl-5- (o-tolyl) octahydro- benzo [c] isoxazole;
• rac-(3aR, 5R, 7R, 7aR) -5- (3-chloro-2-methylphenyl) -1 , 3, 3, 5, 7- pentame- thyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7R, 7aR) -5- (4-fluoro-2-methylphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7R, 7aR) -5- (4-methoxyphenyl) -1 , 3, 3, 5, 7-pentamethyloctahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (2- (methylthio) phenyl) octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (2, 4, 5-trimethylphenyl) octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (2-methyl-5- (trifluorome- thyl) phenyl) octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (4- (methylthio) phenyl) octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (5-methylthiophen-2-yl) oc- tahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (5-methylthiophen-3-yl) oc- tahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (m-tolyl) octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (naphthalen-1 -yl) octahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (naphthalen-2-yl) octahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (o-tolyl) octahydrobenzo [c] isoxazole; • rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (p-tolyl) octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5-phenyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5-propyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 7-tetramethyl-5- (3-methylbut-2-en-1 -yl) octahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 7-tetramethyl-5- (o-tolyl) octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 7-tetramethyl-5-phenyloctahydrobenzo [c] isox- azole;
• rac-(3aR, 5R, 7S, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyl-5- (3-methylbut-2-en-1 -yl) octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyl-5- (o-tolyl) octahydro- benzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyl-5-phenyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyloctahydrobenzo [c] isoxa- zole;
• rac- (3aR, 5R, 7S, 7aR) -1 -ethyl-5- (2-methoxyphenyl) -3, 3, 7-trimethyloctahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 5, 7-tetramethyl-5- (3-methylbut-2-en- 1 -yl) octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 5, 7-tetramethyl-5- (o-tolyl) octahydro- benzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 5, 7-tetramethyl-5-phenyloctahydro- benzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 5, 7-tetramethyl-5-propyloctahydro- benzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 7-trimethyl-5- (3-methylbut-2-en-1 -yl) octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 7-trimethyl-5- (o-tolyl) octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 7-trimethyl-5-phenyloctahydrobenzo [c] isoxazole; • rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-5- (2-methoxyphenyl) -3, 3, 5, 7-tetra- methyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-5- (2-methoxyphenyl) -3, 3, 7-trimethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-5- (4-methoxyphenyl) -3, 3, 5, 7-tetra- methyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-5- (6-methoxypyridin-2-yl) -3, 3, 5, 7-tetra- methyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2, 3-dimethylphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2, 4-difluorophenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2, 4-dimethylphenyl) -1 , 3, 3, 5, 7-pentamethylocta- hydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2, 4-dimethylphenyl) -1 , 3, 3, 7-tetramethyloctahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2, 5-difluorophenyl) -1 , 3, 3, 5, 7-pentamethylocta- hydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2, 5-dimethylphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2, 5-dimethylphenyl) -1 , 3, 3, 7-tetramethyloctahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2, 6-dimethylphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2-ethoxyphenyl) -1 , 3, 3, 5, 7-pentamethyloctahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2-ethylphenyl) -1 , 3, 3, 5, 7-pentamethylOctahydro- benzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2-ethylphenyl) -1 , 3, 3, 7-tetramethyloctahydro- benzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2-ethylphenyl) -1 -isopropyl-3, 3, 7-trimethyloctahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2-fluorophenyl) -1 , 3, 3, 5, 7-pentamethyloctahydro- benzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (2-methoxyphenyl) -1 , 3, 3, 5, 7-pentamethyloctahy- drobenzo [c] isoxazole; • rac-(3aR, 5R, 7S, 7aR) -5- (2-methoxyphenyl) -1 , 3, 3, 7-tetramethyloctahydro- benzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (3, 4-difluorophenyl) -1 , 3, 3, 5, 7-pentamethylocta- hydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (3, 5-difluorophenyl) -1 , 3, 3, 5, 7-pentamethylocta- hydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (3, 5-dimethoxyphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (3, 5-dimethylphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (3, 5-dimethylphenyl) -1-isopropyl-3, 3, 5, 7-tetra- methyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (3- chloro-2-methylphenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (3-chloro-2-methylphenyl) -1 -isopropyl-3, 3, 7-trime- thyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (3-fluoro-5- (trifluoromethyl) phenyl) -1 , 3, 3, 5, 7- pentamethyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (3-fluorophenyl) -1 , 3, 3, 5, 7-pentamethyloctahydro- benzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (3-isopropylphenyl) -1 , 3, 3, 5, 7-pentamethyloctahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (3-methoxyphenyl) -1 , 3, 3, 5, 7-pentamethyloctahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (4- (tert-butyl) phenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (4- (tert-butyl) phenyl) -1 , 3, 3, 7-tetramethyloctahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (4- (tert-butyl) phenyl) -1 -isopropyl-3, 3, 7-trimethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (4-chloro-2-methylphenyl) -1 -isopropyl-3, 3, 7-trime- thyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (4-fluoro-2-methoxyphenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (4-fluoro-2-methylphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole; • rac-(3aR, 5R, 7S, 7aR) -5- (4-fluoro-2-methylphenyl) -1 , 3, 3, 7-tetramethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (4-fluorophenyl) -1 , 3, 3, 5, 7-pentamethyloctahydro- benzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (4-fluorophenyl) -1 -isopropyl-3, 3, 5, 7-tetramethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (4-methoxyphenyl) -1 , 3, 3, 5, 7-pentamethyloctahy- drobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (5-chloro-2-methylphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (5-chloro-2-methylphenyl) -1 -isopropyl-3, 3, 7-trime- thyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (5-fluoro-2-methylphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (5-fluoro-2-methylphenyl) -1 , 3, 3, 7-tetramethyl- octahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (benzo [d] [1 , 3] dioxol-5-yl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5- (furan-3-yl) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazole;
• rac- 3aR, 5R, 7S, 7aR) -5, 7-diethyl-1 -isopropyl-3, 3-dimethyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 5R, 7S, 7aR) -5-isopentyl-1 -isopropyl-3, 3, 5, 7-tetramethyloctahydro- benzo [c] isoxazole;
• rac-(3aR, 5S, 7aR) -1 , 3, 3, 5-tetramethyl-5- (3-methylbut-2-en-1 -yl) octahydro- benzo [c] isoxazole;
• rac-(3aR, 7aR) -1 , 3, 3, 4, 5, 7-hexamethyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 7aR) -1 , 3, 3-trimethyl-6-phenyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 7aR) -1 , 5, 7-triethyl-3, 3- dimethyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 7aS) -1 , 3, 3, 4, 5, 7-hexamethyloctahydrobenzo [c] isoxazole;
• rac-(3aR, 7S, 7aR) -5, 5-diethyl- 1 , 3, 3, 7-tetramethyloctahydrobenzo [c] isoxa- zole;
• rac-(3aS, 5R, 7S, 7aS) -5- (4-fluorophenyl) -1 , 3, 3, 5, 7-pentamethyloctahydro- benzo [c] isoxazole; • rac-(3aS, 5S, 7S, 7aS) -1 -ethyl-3, 3, 7-trimethyl-5- (3-methylbut-2-en-1 -yl) oc- tahydrobenzo [c] isoxazole;
• rac-2-chloro-5- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
• rac-2-chloro-5- ((3aS, 5R, 7R, 7aS) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
• rac-2-methyl-5- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
• rac-3-((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxa- zol-5-yl) benzonitrile;
• rac-3-((3aR, 5R, 7S, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyloctahydrobenzo [c] isox- azol-5-yl) -4-methylbenzonitrile;
• rac-3-((3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 5, 7-tetramethyloctahydrobenzo [c] isoxazol-5-yl) -4-methylbenzonitrile;
• rac-3-((3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 5, 7-tetramethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
• rac-3-((3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 7-trimethyloctahydrobenzo [c] isox- azol-5-yl) -4-methoxybenzonitrile;
• rac-3-chloro-5- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
• rac-3-methyl-4- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
• rac-4- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxa- zol-5-yl) benzonitrile;
• rac-4-methoxy-3- ((3aR, 5R, 7R, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
• rac-4-methoxy-3- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
• rac-4-methyl-2- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
• rac-4-methyl-3- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
• rac-4-methyl-3- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 7-tetramethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
• rac-methyl 4-methyl-3- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydro- benzo [c] isoxazol-5-yl) benzoate; • rel-4-methyl-3- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile and
• rel-4-methyl-3- ((3aS, 5S, 7R, 7aS) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile.
Definitions
[0042] As used hereinabove the prefix "rac" refers to the relative stereochemistry of the respective descriptors (R, S) disclosing the racemic mixture of both enantiomers; the prefix "rel" refers to the relative stereochemistry of the respective descriptors (R, S) referring to a single, unassigned enantiomer. Chemical names with no stereochem- ical descriptor (i.e. neither R nor S) refer to mixtures of diastereomers and enantiomers.
[0043] As used in relation to compounds of formula (I) (which encompass the com- pounds of formula (la) and (lb)) unless otherwise indicated "alkyl" refers to linear or branched alkyl, "alkenyl" refers to linear or branched alkyl comprising at least one car- bon-to-carbon double bond, e.g. 2 or 3 double bonds; and "cycloalkenyl" refers to cy- cloalkyl comprising at least one carbon-to-carbon double bond with the proviso that the ring is not saturated.
[0044] The compounds as defined by formula (I) (which encompass the compounds of formula (la) and (lb)) comprise several chiral centers and as such may exist as a mix- ture of stereoisomers, or they may be resolved as isomerically pure forms. Resolving stereoisomers Ads to the complexity of manufacture and purification of these com- pounds and so it is preferred to use the compounds as mixtures of their stereoisomers simply for economic reasons. However, if it is desired to prepare individual stereoiso- mers, this may be achieved according to methods known in the art, e.g. preparative HPLC and GC, crystallization or stereoselective synthesis. Accordingly, the chemical structures depicted herein encompass all possible stereoisomers forms of the illus- trated compounds.
[0045] It is also noted that the compounds as defined by formula (I) (which encompass the compounds of formula (la) and (lb)) may exist in unsolvated forms as well as solv- ated forms, including hydrated forms and as N-oxides. In general, compounds may be hydrated, solvated or N-oxides. Certain compounds may exist in multiple crystalline or amorphous forms. In general, all physical forms are equivalent for the uses contem- plated herein and are intended to be within the scope of the present invention.
[0046] "Solvate" means a compound formed by solvation (the combination of solvent molecules with molecules or ions of the solute), or an aggregate that consists of a solute ion or molecule, i.e., a compound as defined by formula (I) (which encompass the compounds of formula (la) and (lb)), with one or more solvent molecules. When water is the solvent, the corresponding solvate is "hydrate". Further suitable solvents can be but are not limited to: acetone, acetonitrile, benzene, cyclohexane, dihy- drolevoglucosenone, methyl-tetrahydrofuran, pentylene glycol, ethylene glycol, petro- leum ether, ethyl lactate, methyl lactate, propyl lactate, diethylether, tert-butyl methyl ether, dimethylsulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, dioxane, ethanol, ethyl acetate, ethylene glycol, diethylene glycol, propylene glycol, heptane, hexane, methanol, toluene and xylene.
[0047] "Salt" refers to a salt of a compound as defined by formula (I) (which encompass the compounds of formula (la) and (lb)), which possesses the desired pharmacological activity of the parent compound. Such salts include: (1 ) acid Addition salts, formed with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like; or formed with organic acids such as amino acids, acetic acid, trifluoroacetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3- (4-hydroxybenzoyl) benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1 , 2- ethane-disulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, 4-chloro- benzenesulfonic acid, 2-naphthalenesulfonic acid, 4-toluenesulfonic acid, camphorsul- fonic acid, 4-methylbicyclo [2.2.2] -oct-2-ene-1 -carboxylic acid, glucoheptonic acid, 3- phenylpropionic acid, trimethylacetic acid, tertiary butylacetic acid, lauryl sulfuric acid, gluconic acid, glutamic acid, hydroxynaphthoic acid, salicylic acid, stearic acid, mu- conic acid, and the like; or (2) salts formed when an acidic proton present in the parent compound is replaced by a metal ion, e.g., an alkali metal ion, an alkaline earth ion, or an aluminum ion; or coordinates with an organic base such as ethanolamine, diethan- olamine, triethanolamine, N-methylglucamine and the like.
PHYSIOLOGICAL COOLING AGENTS
[0048] Physiological cooling agents forming group (b1 ) are chemical substances initi- ating a cooling effect when brought into contact with human skin or mucosa. Typically, these agents represent menthol or menthol compounds are preferably selected from the group formed by the species depicted in the following table (including their optical isomers and racemates):
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0002
Menthol derivatives
[0049] A first important representative of the substances forming component (b) is mono-menthyl succinate, which as a substance was patented as early as 1963 by
Brown & Williamson Tobacco Corp. (US 3,1 1 1 ,127) and as a refrigerant is the subject of property rights US 5,725,865 and 5,843,466 (V.Mane Fils). Both the succinate and the analogous monomenthyl glutarate are important representatives of monomenthyl esters based on di- and polycarboxylic acids:
Figure imgf000024_0001
[0050] Examples of applications of these substances can be found, for example, in the printed documents WO 2003 043431 (Unilever) or EP 1332772 A1 (IFF).
[0051] The next important group of menthol compounds preferred in the sense of the invention comprises carbonate esters of menthol and polyols, such as glycols, glycerol or carbohydrates, such as menthol ethylene glycol carbonates, menthol propylene gly- col carbonates, menthol 2-methyl-1 ,2-propanediol carbonates or the corresponding sugar derivatives:
Figure imgf000025_0001
[0052] The use of such substances as a cooling agent for cigarettes is, for example, the subject of the 1968 publication US 3,419,543 (Mold et al.); their use as a physio- logical cooling agent is claimed in DE 4226043 A1 (H&R). [0053] In the sense of the invention, the menthol compounds menthyl lactate) and, in particular, menthone glyceryl acetal or menthone glyceryl ketal are preferred.
Figure imgf000025_0002
[0054] The former structure is obtained by esterification of lactic acid with menthol, the latter by acetylation of menthone with glycerol (cf. DE 2608226 A1 , H&R). This group of compounds also includes 3-(l-menthoxy)-1 ,2, propanediol, also known as Cooling Agent 10 (US 6,328,982, TIC), and 3-(l-menthoxy)-2-methyl-1 ,2, propanediol, which has an Additional methyl group.
Figure imgf000025_0003
[0055] For example, 3-(l-menthoxy)-1 ,2, propanediol is prepared starting from menthol according to the following scheme (see US 4,459,425, Takasago):
Figure imgf000026_0001
[0056] Alternative routes in which menthol is reacted with epichlorohydrin in the first step are described in US 6,407,293 and US 6,515,188 (Takasago). The following is an overview of preferred menthol compounds characterized by CO bonding:
Figure imgf000026_0002
[0057] Among these substances, menthone glyceryl acetal/ketal and menthyl lactate as well as menthol ethylene glycol carbonate and menthol propylene glycol carbonate. WS cooling agents
[0058] In the 1970s, menthol compounds were developed for the first time which have a C-C bond in the 3-position and of which a number of representatives can also be used in the sense of the invention. These substances are generally referred to as WS types. The basic body is a menthol derivative in which the hydroxyl group is replaced by a carboxyl group (WS-1 ). All other WS types are derived from this structure, such as the species WS-3, WS-4, WS-5, WS-12, WS-14 and WS-30, which are also pre- ferred in the sense of the invention. The following two diagrams show the synthesis routes:
Figure imgf000027_0001
[0059] The esters derived from WS-1 are described, for example, in US 4,157,384, and the corresponding N-substituted amides in J. Soc. Cosmet. Chem. pp. 185-200 (1978).
[0060] Physiological cooling agents which are particularly preferred encompass the fol- lowing species: Menthol
Menthol glyceryl acetal
Menthol glyceryl ketal
Menthol menthyl ether
Menthone glyceryl acetal
Menthone glyceryl ketal
Menthoxy-1 ,2-propandiol
Menthoxy-2-methyl-1 ,2-propanediol
Menthyl acetate
Menthyl ethylene glycol carbonate
Menthyl formiate
Menthyl glutamate
Menthyl glycerol carbonate
Menthyl hydroxy isobutyrate
Menthyl isobutyrate
Menthyl lactate
Menthyl malonate
Menthyl methyl ether
Menthyl N-ethyl oxamate
Menthyl propylene glycol carbonate
Menthyl pyroglutamate
Menthyl-(2-methoxy)acetate
Menthyl-(2-methoxyethoxy)acetate
Menthyl succinate
O-Menthyl succinic acid ester amide
O-Menthyl succinic acid ester-NN-(dimethyl)amide
Menthane carboxylic acid-N-(4-cyanophenyl)amide
Menthane carboxylic acid-N-(4-cyanomethylphenyl)amide
Menthane carboxylic acid-N-ethylamide (WS-3)
(WS-4)
Nα-(menthane carbonyl) glycine ethylester (WS-5)
(1 R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1 -isopropyl)cyclohex- ane-carboxamide (WS-12) • (WS-14)
• 2,3-dimethyl-2-(2-propyl)-butyric acid-N-methylamide (WS23)
• Isopulegol acetate
• p-Menthane-3,8-diol
• Cubebol
• 3-Methyl-2(1 -pyrrolidinyl)-2-cyclopentene-1 -one)
• Tetrahydropyrimidine-2-one
• N-(2-(pyridin-2-yl)ethyl)-3-p-menthanecarboxamide
• [(1 R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] 2-(ethylamino)-2-oxo- acetate
Physiological warming agents
[0061] Physiological warming agents forming group (b2) are chemical substances ini- tiating a warming effect when brought into contact with human skin or mucosa. Suitable warming agents encompass the following species:
• vanillyl derivatives, preferably vanillyl ethers
• capsaicin;
• allyl isothiocyanate;
• gingerol;
• 4-(l-menthoxymethyl)-2-phenyl-l;3-dioxolan;
• 4-(l -menthoxymethyl)-2-(3';4'-dihydroxyphenyl)-l;3-dioxolan;
• 4-(l-menthoxymethyl)-2- (2'-hydroxy-3 '-methoxyphenyl)-3-dioxolan;
• 4-(l-menthoxymethyl)-2-(4'-methoxyphenyl)-3-dioxolan;
• 4-(l-menthoxymethyl)-2-(3';4'methylenedioxyphenyl)-3 -dioxolan;
• 4-(l-menthoxymethyl)-2-(3 '-methoxy-4'-hydroxyphenyl) -3 -dioxolan;
• red pepper oil;
• red pepper oleoresin;
• ginger oleoresin;
• nonylic acid vanillyl amide;
• jambu oleoresin;
• Zanthoxylum pieritum extract;
• sanshool I; • sanshool II;
• sanshoamide;
• black pepper extract;
• chavicine;
• piperine;
• spilanthol;
• the modulators or warming agents disclosed in US 6,780,443 (as far as the nature of the modulators are concerned this document is hereby incorporated by reference) and mixtures thereof.
[0062] In a preferred embodiment said warming agent represent a vanillyl ether ac- cording to formula (I)
Figure imgf000030_0001
wherein R1 stands for hydrogen, or a C1-C7 alkyl group; R2 stands for a C1-C3 alkyl group, R3 stands for hydrogen or a C3-C9 alkoxyl group; R4 stands for hydroxyl or a - OC(O)CH3 group; and wherein R2 and R3 can be covalent bounded to form a cyclic acetal; said acetal optionally substituted by a C2-C8 alkyl group.
[0063] In a particularly preferred embodiment said warming agents represent a vanillyl ether according to formula (II)
Figure imgf000030_0002
wherein R1 stand for hydrogen or a C1-C7 alkyl group.
[0064] Most preferred said warming agents represent a vanillyl ether according to for- mula (III)
Figure imgf000031_0001
Aroma or flavoring compounds
[0065] Aroma compounds and flavouring agents forming group (c) are well known in the art and can be chosen from synthetic flavouring liquid and/or oils derived from plants leaves, flowers, fruits and so forth, and combinations thereof. Representative flavouring liquids include: artificial, natural or synthetic fruit flavours such as eucalyp- tus, lemon, orange, banana, grape, lime, apricot and grapefruit oils and fruit essences including apple, strawberry, cherry, orange, pineapple and so forth; bean and nut de- rived flavours such as coffee, cocoa, cola, peanut, almond and so forth; and root de- rived flavours such as licorice or ginger. Also solid aroma and flavoring compounds, for example in the form of salts can be used.
[0066] Suitable aroma or flavouring compounds encompass the following species:
• 12-methyltridecanal;
• acetaldehyde;
• acetanisole;
• acethylthiazole-2;
• acethylthiazoline-2;
• acetic acid; acetyl methylcarbinol; acetyl pyrazine-2; acetyl pyridine-2; allyl capronate; allyl isothiocyanate; amyl cinnamaldehyde-alpha; anethole; anisaldehyde-para; anisic alcohol; benzaldehyde; benzyl acetate; borneol-l; butyl acetate; butylidene phthalide-3; butyric acid; camphor; caproic acid; carvacrol; carvomenthone; carvo n-d; carvon-l; carvylacetate-cis; caryophyllene; cineole-1 ;4; cineole-1 ;8; cinnamalcohol; cinnamaldehyde; cinnamyl acetate; citral; citronellal; citronellol; citronellyl acetate; cresol cuminaldehyde; cyclopentadecanolide; damascenone-alpha; damascenone-beta; damascone-alpha; damascoe-beta; decadienal-2;4; decadienal-2;4; decalactone delta; decalacton gamma; decanal; dehydromenthofurolactone; diallyl disulfide; diethylpyrazine-2;3; dihydroanethol; dihydrocarvone; dihydrocoumarin; dihydroionone-beta; dihydromenthofurolactone; dihydronootkatone; dimethyl lanthranilate; dimethyl isopropyldithiazine; dimethyl pyrazine; dimethyl sulfide; diphenyloxide; divanilline; d-menthol; d-menthone; d-menthyl acetate; dodecalactone-delta; dodecalactone-gamma; epithiomenthan-1 ;8; ethyl acetate; ethyl butyrate; ethyl capronate; ethyl caprylate; ethyl cinnamate; ethyl isobutyrate; ethyl isovaleria-nate; ethyl lactate; ethyl maltol; ethyl methyl butyrate-2; ethyl methyl thiopropionate; ethyl phenol-4; ethyl vanillin; eugenol; fenchol; filbertone; frambinone methyl ether; frambinone; furaneol; furfurylthiol; geraniol; geranyl acetate; geranyl isobutyrate; guaiacol; heliotropin; heptalactone-gamma; heptanone-2; heptenal-Z-4; hexalactone-gamma; hexanal hexanol; hexenol-E-2; hexenol-Z-3; hexenyl acetate-E-2; hexenyl acetate-Z-3; hexenyl capronate-Z-3; hexyl acetate; hexyl cinnamaldehyde-alpha; hotrienol; indole; ionon-beta; ionone-alpha; isoamyl acetate; isoamyl butyrate; isoamyl isovaerianate; isobutyl acetate; isobutyl thiazole; isobutylmethoxypyrazine isobutyraldehyde; isoeugenol;
Isomenthon; isopropylmethoxypyrazine; isopropylmethylpyrazine-2;4; isopulegol; isova-leraldehyde; jasmine lactone; jasmon cis; ketoisophorone; limonene-d; linalool oxide; linalool-d; linalool-l; linalyl acetate; l-menthol; l-menthone; l-menthyl acetate; maltol; massoilactone; melonal; menthadienyl acetate; menthofurolactone; menththiol-1 ;8; methional; methoxymethylpyrazine-2;3; methyl anthranilate; methyl butyl acetate-2; methyl butyrate; methyl cinnamate; methyl dihydrojasmonate; methyl furanthiol-2;3; methyl jasmonate; methyl salicylate; methyl tetrahydrofuranthiol-2;3; methyl thiobutyrate; methyl thiohexyl acetate-1 ;3; methylcyclopen-tenolone; methylthiohexanol-1 ;3; myrtenal; naringin; neo-menthol; neral; nerol; nerylacetate; nonadienal-2;4; nonadienal-2;6; nonalactone delta; nonalactone gamma; nonenal-E-2; nonenal-Z-6; nonenol-Z-6; nootkatone; octalactone gamma; octalactone delta; octanal octenol-1 ;3; pellitorin; pentenone-1 ;3; pentyl acetate; phenyl ethyl acetate; phenyl ethyl alcohol; phenyl acetaldehyde; pinene-alpha; pinene-beta; piperitanate; piperitone prenyl thioacetate; prenyl thiol; reubenamine; rose oxide; rubescenamine; sabinene hydrate; scatole; sotolone; sty roly I acetate; terpinenol-4; terpineol; thiohexanol-1 ;3; thiohexyl acetate-1 ;3; thiomenthanone-8;3; thiopentanone-4;4;2; thymol; • tridecatrienal;
• trimethyl pyrazine;
• undecadienal-2;4;
• undecalactone-gamma and delta;
• undecatriene;
• vanillin;
• vinyl guaiacol;
• whisky lactone; and mixtures thereof.
[0067] In particular preferred aroma or flavouring compounds encompass menthol, cin- eol, eugenol, thymol, cinnamic aldehyde, peppermint oil, spearmint oil, eucalyptus oil, thyme oil, cinnamon oil, clove oil, spruce needle oil, fennel oil, sage oil, aniseed oil, star anise oil, chamomile oil, and caraway oil, and their mixtures.
Fragrances
[0068] The fragrances forming group (d) can be used as single components or in the form of more or less complex mixtures. The species may be obtained from natural sources or prepared by organic synthesis.
Natural perfumes
[0069] Natural perfumes include the extracts of blossoms (lily, lavender, rose, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, orange), roots (nutmeg, an- gelica, celery, cardamom, costus, iris, calmus), woods (pinewood, sandalwood, guaiac wood, cedarwood, rosewood), herbs and grasses (tarragon, lemon grass, sage, thyme), needles and branches (spruce, fir, pine, dwarf pine), resins and balsams (gal- banum, elemi, benzoin, myrrh, olibanum, opoponax). Animal raw materials, for exam- ple civet and beaver, may also be used.
[0070] Typically, the synthetic fragrances represent aldehydes, ketones, alcohols, ethers, esters, hydrocarbons their mixtures. In the following these types of fragrances are illustrated but not limited by examples:
Aldehydes
[0071] Examples for suitable fragrances showing an aldehyde structure encompass melonal, triplal, ligustral, adoxal, anisaldehyde, cymal, ethylvanillin, florhydral, flo- ralozon, helional, heliotropin, hydroxycitronellal, koavon, laurinaldehyde, canthoxal, ly- ral, lilial, adoxal, anisaldehyde, cumal, methyl-nonyl-acetaldehyde, citronellal, citronel- lyloxy-acetaldehyde, cyclamenaldehyde, bourgeonal, p-tert.-bucinal, phenylacetalde- hyde, undecylenaldehyde, vanillin; 2,6,10-trimethyl-9-undecenal, 3-dodecen-l-al, a-n- Amylzimtaldehyde, 4-methoxy-benz-aldehyde, benzaldehyde, 3-(4-tert-butylphenyl)- propanal,2-methyl-3-(para-methoxy-phe-nylpropanal), 2-methyl-4-(2,6,6-trimethyl- 2(1 )-cyclohexen-1 -yl)butanal,3-phenyl-2-pro-penal, cis-/trans-3,7-dimethyl-2,6-octa- dien-l-al, 3,7-dimethyl-6-octen-l-al,[(3,7-dimethyl-6-octenyl)-xy]-cetaldehyde, 4-iso- propylbenzyaldehyde, 1 ,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthaldehyde, 2,4- dimethyl-3-cyclohexen-1 -carboxyaldehyde, 2-methyl-3-(isopropyl-phenyl)propanal, decyl aldehyde, 2,6-dimethyl-5-heptenal; 4-(tricyclo[5.2.1 .0 (2,6)]-decylidene-8)-buta- nal; octahydro-4, 7-methano-IH-indenecarboxaldehyde; 3-ethoxy-4-hydroxybenzalde- hyde, para-ethyl-alpha,alpha-dimethylhydrozimtaldehyde, a-methyl-3,4-(methylenedi- oxy)-hydrocinnamaldehyde, 3,4-methylenedioxybenzaldehyde, a-n-hexyl-cinnamalde- hyde, m-cymene-7-carboxaldehyde, a-methylphenylacetaldehyde, 7-hydroxy-3,7-di- methyl octanal, undecenal, 2,4,6-trimethyl-3-cyclohexene-l-carboxalde-hyde,4-(3)(4- methyl-3-pentenyl)-3-cyclohexen-carboxaldehyde, 1 -dodecanal, 2,4-dimethyl-cyclo- hexene-3-carboxaldehyde,4-(4-hydroxy-4-methylpentyl)-3-cylohexene-l-carboxal-de- hyde, 7-methoxy-3,7-dimethyloctan-1 -al, 2-methyl undecanal, 2-methyl decanal, 1 - nonanal, 1 -octanal, 2,6,10-trimethyl-5,9-undecadienal, 2-methyl-3-(4- tertbutyl)propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 3-(4-methoxyphenyl)-2- methylpropanal, methylno-nylacetaldehyde, 2-phenylpropan-1 -al, 3-phenylprop-2-en- 1-al, 3-phenyl-2-pentylprop-2-en-1 -al, 3-phenyl-2-hexylprop-2-enal, 3-(4-iso- propylphenyl)-2-methylpropan-1 -al, 3-(4-ethylphenyl)-2,2-dimethylpropan-1 -al, 3-(4- tert-butylphenyl)-2-methyl-propanal, 3-(3,4-Methylendioxy-phenyl)-2-methylpropan-1 - al,3-(4-Ethylphenyl)-2,2-dimethylpropanal, 3-(3-lsopropylphenyl)-butan-1 -al, 2,6-Di- methylhept-5-en-1 -al,Dihydrozimtaldehyde, 1 -methyl-4-(4-methyl-3-pentenyl)-3-cyclo- hexene-1 -carboxaldehyde, 5- or 6-Methoxyhexahydro-4,7-methanoindan-1 or 2-car- boxyaldehyde, 3,7-dimethyloctan-1 -al, 1 -undecanal, 10-undecen-1 -al, 4-hydroxy-3- methoxybenzaldehyde, 1 -methyl-3-(4-methylpentyl)-3-cyclohexene-carboxyaldehyde, 7-hydroxy-3,7-dimethyl-octanal; trans-4-decenal, 2,6-nonadienal, p-tolylacetaldehyde; 4-methylphenylacetaldehyde, 2-methyl-4-(2,6,6-trimethyl-1 -cyclohexen-1 -yl)-2-bu- tenal, o-methoxyzimtaldehyde, 3,5,6-trimethyl-3-cyclohexenecarboxaldehyde, 3,7-di- methyl-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-metha- noindan-1 -carboxaldehyde, octanal, 2-methyl octanal, alpha-methyl-4-(l-meth- ylethyl)benzene-acetaldehyde, 6,6-dimethyl-2-norpinene-2-propionaldehyde, p-me- thyl phenoxy acetaldehyde, 2-methyl-3-phenyl-2-propen-1 -al, 3,5,5-trimethylhexanal, hexahydro-8, 8-dimethyl-2-naphthaldehyde, 3-propyl-bicyclo[2.2.1 ]-hept-5-ene-2- carbaldehyde, 9-decenal, 3-methyl-5-phenyl-1 -pentanal, methylnonyl acetaldehyde, 1 - p-menthene-q-carboxaldehyde, citral or its mixtures, lilial citral, 1 -decanal, n-undeca- nal, n-dodecanal, hlorhydral, 2,4-dimethyl-3-cyclohexen-1 -carboxaldehyde 4-methox- ybenzaldehyde, 3-methoxy-4-hydroxy-benzalde-hyde, 3-ethoxy-4-hydroxybenzalde- hyde, 3,4-methylendioxybenzaldehyde, 3,4-dimethoxybenzaldehyde and their mix- tures.
Ketones
[0072] Examples for suitable fragrances showing a ketone structure encompass buc- coxime, iso jasmone, methyl beta naphthyl ketone, moschus indanone, tonalid/mos- chus plus, α-damascone, β-damascon, δ-damascone, Iso-damascone, damascenone, damarose, methyl-dihydrojasmonate, menthone, carvone, campher, fenchone, al- phalonen, β-iononw, dihydro- β-lonone, y-methylionone, fleuramone, dihydrojasmone, cis-Jasmon, iso-E-Super, methyl cedrenylk etone, or methyl cedrylon, acetophenone, methyl aceto phenone, p-methoxyacetophenone, methyl-β-naphtyl ketone, benzy- lacetone, benzophenone, p-hydroxy phenylbutanone, celery Ketone or livescon, 6- osopropyl-deca-hydro-2-naphtone, dimethyloctenone, freskomenth, 4-(l-ethoxyvinyl)- 3,3,5,5,-tetramethylv cyclohexanone, methylheptenone, 2-(2-(4-Methyl-3-cyclohexen- 1 -yl)propyl)-cyclopentanone, 1 -(p-men-thene-6(2)-yl)-1 -propanone, 4-(4-Hydroxy-3- methoxyphenyl)-2-butanone, 2-Acetyl-3,3-di-methyl-norbornan, 6,7-dihydro-1 ,1 ,2,3,3- pentamethyl-4(5H)-indanone, 4-damascol, dulcinyl or cassione, gelsone, hexalone, isocyclemone E, Methylcyclocitrone, methyl lavender ketone, orivone, p-tert-butyl cy- clohexanone, verdone, delphone, muscone, neobutenone, plicatone, veloutone, 2,4,4,7-tetramethyl-oct-6-en-3-one, tetrameran, hedion and their mixtures. The preferred ketones are selected from the group comprising a-damascone, δ- damascone, iso-damascone, carvone, γ-methyl ionone, Iso-E-Super, 2,4,4,7-tetrame- thyl-oct-6-en-3-one, benzylacetone, β-damascone, damascenone, methyl dihydro- jasmonate, methyl cedrylone, hedione and their mixtures
[0073] As explained above, said ketones or said aldehydes may show an aliphatic, cycloaliphatic, aromatic, ethylenically unsaturated structure or a mixture of these ele- ments. The components may also include heteroatoms or show a polycyclic structure. Suitable substituents for all these structures are hydroxyl and/or amino groups. Further fragrances are compiled in the following document: Steffen Arctander " Published 1960 and 1969 respectively, Reprinted2000 ISBN: Aroma Chemicals Vol. 1 : 0-931710-37- 5, Aroma Chemicals Vol. 2: 0-931710-38-3“, which is hereby incorporated by refer- ence.
Alcohols
[0074] Suitable fragrance alcohols encompass for example 10-undecen-1 -ol, 2,6-di- methylheptan-2-ol, 2-methylbutanol, 2-methylpentanol,2-phenoxyethanol, 2-phe- nylpropanol, 2-tert-Butycyclohexanol, 3,5,5-trimethylcyclohexanol, 3-hexanol, 3-me- thyl-5-phenylpentanol, 3-octanol, 1 -octen-3-ol, 3-phenylpropanol,4-heptenol, 4-iso- propylcyclohexanol, 4-tert-butycyclohexanol, 6,8-dimethyl-2-nonanol,6-nonen-1 -ol, 9- decen-1 -ol, α-methyl benzylalcohol, α-terpineol, amylsalicylat, benzyl alcohol, benzyl salicylate, β -terpineol, butyl salicylate, citronellol, cyclohexyl salicylate, decanol, dihy- dromyrcenol, dimethyl benzylcarbinol, dimethyl heptanol, dimethyl octanol, ethyl salic- ylate, ethyl vanilin, anethol, eugenol, geraniol, heptanol, hexyl salicylat, isoborneol, isoeugenol, isopulegol, linalool, menthol, myrtenol, n-hexanol, nerol, nonanol, octanol, para-menthan-7-ol, phenylethylalkohol, phenol, phenyl salicylat, tetrahydro geraniol, tetrahydro linalool, thymol, trans-2-cis-6-nonadienol, trans-2-nonen-1 -ol, trans-2-oc- tenol, undecanol, vanillin, cinnamalcohol and their mixtures.
Esters
[0075] Examples for suitable fragrances showing a ketone structure encompass benzyl acetate, phenoxyisobutyrate, p-tert.-butylcyclohexylacetate, linalylacetate, dime- thylbenzylcarbinylacetate (DMBCA), phenylethylacetate, benzylacetate, ethylme- thylphenylglycinate, allylcyclohexylpropionate, styrallylpropionate, benzylsalicylate, cyclohexylsalicylate, floramat, melusat, jasmacyclatat and their mixtures. Ethers
[0076] Examples for suitable fragrances showing a ketone structure encompass ben- zylethyl ether or ambroxan. Hydrocarbons
[0077] Examples for suitable fragrances representing hydrocarbons encompass ter- penes, e.g. limonene and pinen.
[0078] Fragrances which are particularly preferred encompass the following species:
• [(3,7-dimethyl-6-octenyl)-xy]-cetaldehyde,
• 1 -(p-menthene-6(2)-yl)-1 -propanone,
• 1 ,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthaldehyde,
• 10-undecen-1 -al,
• 10-undecen-1 -ol,
• 1 -decanal,
• 1 -dodecanal,
• 1 -methyl-3-(4-methylpentyl)-3-cyclohexene-carboxyalde- hyde,
• 1 -methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1 -carboxal- dehyde,
• 1 -nonanal,
• 1 -octanal,
• 1 -octen-3-ol,
• 1 -p-menthene-q-carboxaldehyde,
• 1 -undecanal,
• 2-(2-(4-Methyl-3-cyclohexen-1 -yl)propyl)-cyclopentanone,
• 2,4,4,7-tetramethyl-oct-6-en-3-one,
• 2,4,6-trimethyl-3-cyclohexene-l-carboxalde-hyde,
• 2,4-dimethyl-3-cyclohexen-1 -carboxaldehyde 4-methoxyben- zaldehyde,
• 2,4-dimethyl-3-cyclohexen-1 -carboxyaldehyde,
• 2,6,10-trimethyl-5,9-undecadienal,
• 2,6,10-trimethyl-9-undecenal, 3-dodecen-1 -al,
• 2,6-dimethyl-5-heptenal;
• 2,6-dimethylhept-5-en-1 -al,
• 2,6-dimethylheptan-2-ol, • 2,6-nonadienal, • 2-acetyl-3,3-di-methyl-norbornan, • 2-methyl decanal, • 2-methyl octanal, • 2-methyl undecanal, • 2-methyl-3-(4-tertbutyl)propanal, • 2-methyl-3-(isopropyl-phenyl)propanal, • 2-methyl-3-(para-methoxy-phenylpropanal), • 2-methyl-3-phenyl-2-propen-1 -al, • 2-methyl-4-(2,6,6-trimethyl-1 -cyclohexen-1 -yl)-2-butenal, • 2-methylbutanol, • 2-methylpentanol, • 2-phenoxyethanol, • 2-phenylpropan-1 -al, • 2-phenylpropanol, • 2-tert-butycyclohexanol, • 3-(3,4-methylendioxy-phenyl)-2-methylpropan-1 -al, • 3-(3-isopropylphenyl)-butan-1 -al, • 3 3-(4-ethylphenyl)-2,2-dimethylpropan-1 -al, • 3-(4-ethylphenyl)-2,2-dimethylpropanal, • 3-(4-isopropylphenyl)-2-methylpropan-1 -al, • 3-(4-methoxyphenyl)-2-methylpropanal, • 3-(4-tert-butylphenyl)-2-methyl-propanal, • 3-(4-tert-butylphenyl)-propanal, • 3,4-dimethoxybenzaldehyde, • 3,4-methylendioxybenzaldehyde, • 3,5,5-trimethylcyclohexanol, • 3,5,5-trimethylhexanal, • 3,5,6-trimethyl-3-cyclohexenecarboxaldehyde, • 3,7-dimethyl-2-methylene-6-octenal, • 3,7-dimethyl-6-octen-1 -al, • 3,7-dimethyloctan-1 -al, • 3-ethoxy-4-hydroxybenzaldehyde, • 3-hexanol,
• 3-methoxy-4-hydroxy-benzaldehyde,
• 3-methyl-5-phenyl-1 -pentanal,
• 3-methyl-5-phenylpentanol,
• 3-octanol,
• 3-phenyl-2-hexylprop-2-enal,
• 3-phenyl-2-pentylprop-2-en-1 -al,
• 3-phenyl-2-propenal,
• 3-phenylprop-2-en-1 -al,
• 3-phenylpropanol,
• 3-propyl-bicyclo[2.2.1 ]-hept-5-ene-2-carbaldehyde,
• 4-(1 -ethoxyvinyl)-3,3,5,5-tetramethyl cyclohexanone,
• 4-(3)(4-methyl-3-pentenyl)-3-cyclohexen-carboxaldehyde,
• 4-(4-hydroxy-3-methoxyphenyl)-2-butanone,
• 4-(4-hydroxy-4-methylpentyl)-3-cylohexene-l-carboxal-de- hyde,
• 4-(tricyclo[5.2.1 ,0(2,6)]-decylidene-8)-butanal;
• 4-damascol,
• 4-heptenol,
• 4-hydroxy acetophenone
• 4-hydroxy-3-methoxybenzaldehyde,
• 4-isopropyl benzyaldehyde,
• 4-isopropyl cyclohexanol,
• 4-methoxy benzaldehyde,
• 4-methylphenyl acetaldehyde,
• 4-tert-butyl cyclohexanol,
• 5,9-dimethyl-4,8-decadienal,
• 5-methoxyhexahydro-4,7-methanoindan-1 -carboxyaldehyde,
• 5-methoxyhexahydro-4,7-methanoindan-2-carboxyaldehyde,
• 6,10-dimethyl-3-oxa-5,9-undecadien-1 -al,
• 6,6-dimethyl-2-norpinene-2-propionaldehyde,
• 6,7-dihydro-1 ,1 ,2,3,3-pentamethyl-4(5H)-indanone,
• 6,8-dimethyl-2-nonanol,6-nonen-1 -ol, • 6-isopropyl-deca-hydro-2-naphtone,
• 6-methoxyhexahydro-4,7-methanoindan-1 -carboxyaldehyde,
• 6-methoxyhexahydro-4,7-methanoindan-2-carboxyaldehyde,
• 7-hydroxy-3,7-dimethyl octanal,
• 7-methoxy-3,7-dimethyloctan-1 -al,
• 9-decen-1 -ol,
• 9-decenal,
• acetophenone,
• adoxal,
• allyl cyclohexylpropionate,
• alphalonen,
• ambroxan,
• amylsalicylat,
• anethol,
• anisaldehyde,
• benzaldehyde,
• benzophenone,
• benzyl acetate,
• benzyl acetone,
• benzyl alcohol,
• benzyl salicylate,
• benzylethyl ether,
• bourgeonal,
• buccoxime,
• butyl lactate,
• butyl salicylate,
• campher,
• canthoxal,
• carvone,
• cassione,
• celery cetone
• chlorhydral,
• cinnamalcohol, • cis-/trans-3,7-dimethyl-2,6-octadien-1 -al,
• cis-jasmon,
• citral or its mixtures,
• citronellal,
• citronellol,
• citronellyl oxyacetaldehyde,
• cumal,
• cyclamenaldehyde,
• cyclohexyl salicylate,
• cymal,
• damarose,
• damascenone,
• decanol,
• decyl aldehyde,
• delphone,
• dihydrojasmone,
• dihydromyrcenol,
• dihydrozimtaldehyde,
• dihydro-β-lonone,
• dimethyl benzylcarbinol,
• dimethyl benzylcarbinylacetate,
• dimethyl heptanol,
• dimethyl octanol,
• dimethyl octenone,
• dulcinyl
• ethyl salicylate,
• ethyl vanilin,
• ethylmethylphenyl glycinate,
• eugenol,
• fenchone,
• fleuramone,
• floralozon,
• floramat, • florhydral,
• gelsone,
• geraniol,
• hedione,
• helional,
• heliotropin,
• heptanol,
• hexahydro-4, 7-methanoindan-1 -carboxaldehyde,
• hexahydro-8, 8-dimethyl-2-naphthaldehyde,
• hexalone,
• hexyl salicylat,
• hydroxycitronellal,
• isoborneol,
• isodamascone,
• isoeugenol,
• isojasmone,
• isopulegol,
• jasmacyclatat,
• koavon,
• laurinaldehyde,
• ligustral,
• lilial citral,
• lilial,
• limonen,
• linalool,
• linalyl acetate,
• livescon,
• lyral,
• m-cymene-7-carboxaldehyde,
• melonal,
• melusat,
• menthol,
• menthone, • methyl acetophenone,
• methyl cedrenyl ketone,
• methyl cedrylon,
• methyl cedrylone,
• methyl cyclocitrone,
• methyl dihydrojasmonate,
• methyl heptenone,
• methyl lavender ketone,
• methyl-dihydrojasmonate,
• methylnonyl acetaldehyde,
• methyl-β-naphthyl ketone,
• moschus indanone,
• muscone,
• myrtenol,
• n-dodecanal,
• neobutenone,
• nerol,
• n-hexanol,
• nonanol,
• n-undecanal,
• octahydro-4, 7-methano-1 H-indenecarboxaldehyde;
• octanal,
• octanol,
• o-methoxyzimtaldehyde,
• orivone,
• p-ethyl-α,α-dimethylhydrozimtaldehyde,
• phenol,
• phenoxyacetaldehyde;
• phenoxyisobutyrate,
• phenyl acetaldehyde,
• phenyl salicylat,
• phenylethyl acetate,
• phenylethyl alcohol, • phenylpropyl alcohol • p-hydroxy phenylbutanone, • pinen • plicatone, • p-menthan-7-ol, • p-methoxy acetophenone, • p-methyl phenoxy acetaldehyde, • p-tert.-bucinal, • p-tert.-butyl cyclohexanone, • p-tert.-butyl cyclohexylacetate, • p-tolyl acetaldehyde; • styrallyl propionate, • tetrahydrogeraniol, • tetrahydrolinalool, • tetrameran, • thymol, • tonalid/moschus plus, • trans-2-cis-6-nonadienol, • trans-2-nonen-1 -ol, • trans-2-octenol, • trans-4-decenal, • triplal, • undecanal, • undecanol, • undecylenraldehyde, • vanillin, • veloutone, • verdone, • α.-methyl-3,4-(methylenedioxy)-hydrocinnamaldehyde, • α-damascone, • α-methyl benzylalcohol, • α-methyl-4-(l-methylethyl)benzene-acetaldehyde, • α-methylphenylacetaldehyde, • α-amyl cinnamaldehyde,
• α-n-hexyl cinnamaldehyde,
• α-terpineol,
• β-damascone,
• β-ionon,
• β-terpineol,
• y-methylionone,
• δ-damascone,
COSMETIC PREPARATIONS
[0079] Another object of the present invention refers to cosmetic preparations compris- ing the compositions as defined above. Said cosmetic preparations can represent skin care, personal care, sun care or hair care product or product formulation, comprising the composition as defined above in a working amount, for example about 0.01 to about 1 wt.-percent., preferably about 0.1 to about 0.5 wt.-percent calculated on the composition(s). The composition may represent for example a cosmetic cream, lotion, spray, emulsion, ointment, gel or mousse and the like.
[0080] The preparations according to the invention may contain antidandruff agents, irritation-preventing agents, irritation-inhibiting agents, antioxidants, astringents, per- spiration-inhibiting agents, antiseptic agents, ant-statics, binders, buffers, carrier ma- terials, chelating agents, cell stimulants, cleansing agents, care agents, deodorizing agents, antiperspirants, softeners, emulsifiers, enzymes, essential oils, fibres, film- forming agents, fixatives, foam-forming agents, foam stabilizers, substances for pre- venting foaming, foam boosters, gelling agents, gel-forming agents, hair care agents, hair-setting agents, hair-straightening agents, moisture-donating agents, moisturizing substances, moisture-retaining substances, bleaching agents, strengthening agents, stain-removing agents, optically brightening agents, impregnating agents, dirt-repellent agents, friction-reducing agents, lubricants, moisturizing creams, ointments, opacifying agents, plasticizing agents, covering agents, polish, gloss agents, polymers, powders, proteins, re-oiling agents, abrading agents, silicones, hair promotion agents, cooling agents, skin-cooling agents, warming agents, skin-warming agents, stabilizers, UV- absorbing agents, UV filters, detergents, thickeners, vitamins, oils, waxes, fats, phos- pholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, a-hydroxy acids, polyhydroxyfatty acids, liquefiers, dyestuffs, colour-protecting agents, pigments, odor- iferous substances, polyols, surfactants, electrolytes, organic solvents or silicone de- rivatives and the like as additional auxiliaries and additives.
Surfactants [0081] Preferred auxiliaries and additives are anionic and/or amphoteric or zwitterionic surfactants. Non-ionic and cationic surfactants can be also present in the composition. Suitable examples are mentioned along with the paragraph dealing with emulsifiers.
[0082] Typical examples for anionic and zwitterionic surfactants encompass: Almon- damidopropylamine Oxide, Almondamidopropyl Betaine, Aminopropyl Laurylgluta- mine, Ammonium C12-15 Alkyl Sulfate, Ammonium C12-16 Alkyl Sulfate, Ammonium Capryleth Sulfate, Ammonium Cocomonoglyceride Sulfate, Ammonium Coco-Sulfate, Ammonium Cocoyl Isethionate, Ammonium Cocoyl Sarcosinate, Ammonium C12-15 Pareth Sulfate, Ammonium C9-10 Perfluoroalkylsulfonate, Ammonium Dinonyl Sul- fosuccinate, Ammonium Dodecylbenzenesulfonate, Ammonium Isostearate, Ammo- nium Laureth-6 Carboxylate, Ammonium Laureth-8 Carboxylate, Ammonium Laureth Sulfate, Ammonium Laureth-5 Sulfate, Ammonium Laureth-7 Sulfate, Ammonium Lau- reth-9 Sulfate, Ammonium Laureth-12 Sulfate, Ammonium Lauroyl Sarcosinate, Am- monium Lauryl Sulfate, Ammonium Lauryl Sulfosuccinate, Ammonium Myreth Sulfate, Ammonium Myristyl Sulfate, Ammonium Nonoxynol-4 Sulfate, Ammonium Nonoxynol- 30 Sulfate, Ammonium Oleate, Ammonium Palm Kernel Sulfate, Ammonium Stearate, Ammonium Tallate, AMPD-lsostearoyl Hydrolyzed Collagen, AMPD-Rosin Hydrolyzed Collagen, AMP-lsostearoyl Hydrolyzed Collagen, AMP-lsostearoyl Hydrolyzed Keratin, AMP-lsostearoyl Hydrolyzed Soy Protein, AMP-lsostearoyl Hydrolyzed Wheat Protein, Apricotamidopropyl Betaine, Arachidic Acid, Arginine Hexyldecyl Phosphate, Avo- cadamidopropyl Betaine, Avocado Oil Glycereth-8 Esters, Babassu Acid, Babassuami- dopropylamine Oxide, Babassuamidopropyl Betaine, Beeswax Acid, Behenamidopro- pyl Betaine, Behenamine Oxide, Beheneth-25, Beheneth-30, Behenic Acid, Behenyl Betaine, Bis- Butyldimethicone Polyglyceryl-3, Butoxynol-5 Carboxylic Acid, Butoxynol-19 Carboxylic Acid, Butyldimoniumhydroxypropyl Butylglucosides Chloride, Butyldimoniumhydroxypropyl Laurylglucosides Chloride, Butyl Glucoside, Butylgluco- side Caprate, Butylglucosides Hydroxypropyltrimonium Chloride, Butyloctanoic Acid, C18-36 Acid, C20-40 Acid, C30-50 Acid, C16-22 Acid Amide MEA, Calcium Do- decylbenzenesulfonate, Calcium Lauroyl Taurate, C9-16 Alkane/Cycloalkane, C10-14 Alkyl Benzenesulfonic Acid, C12-14 Alkyl Diaminoethylglycine HCL, C9-15 Alkyl Phos- phate, Candida Bombicola/Glucose/Methyl Rapeseedate Ferment, Canolamidopropyl Betaine, Capric Acid, Caproic Acid, Caproyl Ethyl Glucoside, Capryl/Capramidopropyl Betaine, Capryleth-4 Carboxylic Acid, Capryleth-6 Carboxylic Acid, Capryleth-9 Car- boxylic Acid, Caprylic Acid, Capryloyl Collagen Amino Acids, Capryloyl Glycine, Capryloyl Hydrolyzed Collagen, Capryloyl Hydrolyzed Keratin, Capryloyl Keratin Amino Acids, Capryloyl Silk Amino Acids, Caprylyl/Capryl Glucoside, Caprylyl/Capryl Wheat Bran/Straw Glycosides, Caprylyl Glucoside, Caprylyl Glyceryl Ether, Caprylyl Pyrrolidone, Carnitine, Ceteareth-20, Ceteareth-23, Ceteareth-24, Ceteareth-25, Ce- teareth-27, Ceteareth-28, Ceteareth-29, Ceteareth-30, Ceteareth-33, Ceteareth-34, Ceteareth-40, Ceteareth-50, Ceteareth-55, Ceteareth-60, Ceteareth-80, Ceteareth- 100, Ceteareth-25 Carboxylic Acid, Ceteareth-2 Phosphate, Ceteareth-4 Phosphate, Ceteareth-5 Phosphate, Ceteareth-10 Phosphate, Ceteth-20, Ceteth-23, Ceteth-24, Ceteth-25, Ceteth-30, Ceteth-40, Ceteth-45, Ceteth-150, Ceteth-8 Phosphate, Ceteth- 10 Phosphate, Ceteth-20 Phosphate, Cetoleth-22, Cetoleth-24, Cetoleth-25, Cetoleth- 30, Cetyl Betaine, Chrysanthemum Sinense Flower Extract, C12-14 Hydroxyalkyl Hy- droxyethyl Beta-Alanine, C12-14 Hydroxyalkyl Hydroxyethyl Sarcosine, Cocami- doethyl Betaine, Cocamidopropylamine Oxide, Cocamidopropyl Betainamide MEA Chloride, Cocamidopropyl Betaine, Cocamidopropyl Hydroxysultaine, Cocamine Ox- ide, Cocaminobutyric Acid, Cocaminopropionic Acid, Coceth-7 Carboxylic Acid, Coceth-4 Glucoside, Cocoamphodipropionic Acid, Cocobetainamido Amphopropio- nate, Coco-Betaine, Cocodimonium Hydroxypropyl Hydrolyzed Rice Protein, Coco- dimonium Hydroxypropyl Hydrolyzed Soy Protein, Cocodimonium Hydroxypropyl Hy- drolyzed Wheat Protein, Coco-Glucoside, Cocoglucosides Hydroxypropyltrimonium Chloride, Coco- Hydroxysultaine, Coco-Morpholine Oxide, Coconut Acid, Coconut Oil Glycereth-8 Esters, Coco/Oleamidopropyl Betaine, Coco-Sultaine, Coco/Sunflow- eramidopropyl Betaine, Cocoylcholine Methosulfate, Cocoyl Glutamic Acid, Cocoyl Hydrolyzed Collagen, Cocoyl Hydrolyzed Keratin, Cocoyl Hydrolyzed Oat Protein, Co- coyl Hydrolyzed Rice Protein, Cocoyl Hydrolyzed Silk, Cocoyl Hydrolyzed Soy Protein, Cocoyl Hydrolyzed Wheat Protein, Cocoyl Sarcosine, Corn Acid, Cottonseed Acid, Cottonseed Oil Glycereth-8 Esters, C10-16 Pareth-1 , C10-16 Pareth-2, C1 1 -13 Pa- reth-6, C1 1 -13 Pareth-9, C1 1 -13 Pareth-10, C1 1 -15 Pareth-30, C1 1 -15 Pareth-40, C12-13 Pareth-1 , C12-13 Pareth- 23, C12-14 Pareth-5, C12-14 Pareth-9, C13-15 Pa- reth-21 , C14-15 Pareth-8, C20-22 Pareth-30, C20- 40 Pareth-40, C20-40 Pareth-95, C22-24 Pareth-33, C30-50 Pareth-40, C9-1 1 Pareth-6 Carboxylic Acid, C9-1 1 Pareth- 8 Carboxylic Acid, C1 1 -15 Pareth-7 Carboxylic Acid, C12-13 Pareth-5 Carboxylic Acid, C12-13 Pareth-7 Carboxylic Acid, C12-13 Pareth-8 Carboxylic Acid, C12-13 Pareth- 12 Carboxylic Acid, C12-15 Pareth-7 Carboxylic Acid, C12-15 Pareth-8 Carboxylic Acid, C12-15 Pareth- 12 Carboxylic Acid, C14-15 Pareth-8 Carboxylic Acid, C6-10 Pa- reth-4 Phosphate, C12-13 Pareth-2 Phosphate, C12-13 Pareth-10 Phosphate, C12-15 Pareth-6 Phosphate, C12-15 Pareth-8 Phosphate, C12-15 Pareth-10 Phosphate, C12- 16 Pareth-6 Phosphate, C4-18 Perfluoroalkylethyl Thiohydroxypropyltrimonium Chlo- ride, Cupuassuamidopropyl Betaine, DEA-C12-13 Alkyl Sulfate, DEA-C12-15 Alkyl Sulfate, DEA-Ceteareth-2 Phosphate, DEA-Cetyl Sulfate, DEA- Cocoamphodipropio- nate, DEA-C12-13 Pareth-3 Sulfate, DEA-Cyclocarboxypropyloleate, DEA- Do- decylbenzenesulfonate, DEA-lsostearate, DEA-Laureth Sulfate, DEA-Lauryl Sulfate, DEA- Linoleate, DEA-Methyl Myristate Sulfonate, DEA-Myreth Sulfate, DEA-Myristate, DEA-Myristyl Sulfate, DEA-Oleth-5 Phosphate, DEA-Oleth-20 Phosphate, DEA PG- Oleate, Deceth-7 Carboxylic Acid, Deceth-7 Glucoside, Deceth-9 Phosphate, Decyla- mine Oxide, Decyl Betaine, Decyl Glucoside, Decyltetradeceth-30, Decyltetradecyla- mine Oxide, Diammonium Lauramido-MEA Sulfosuccinate, Diammonium Lauryl Sul- fosuccinate, Diammonium Oleamido PEG-2 Sulfosuccinate, Dibutoxymethane, Di-CI 2-15 Pareth-2 Phosphate, Di-CI 2-15 Pareth-4 Phosphate, Di-CI 2-15 Pareth-6 Phos- phate, Di- C12-15 Pareth-8 Phosphate, Di-CI 2-15 Pareth-10 Phosphate, Didodecyl Butanetetracarboxylate, Diethylamine Laureth Sulfate, Diethylhexyl Sodium Sulfosuc- cinate, Dihydroxyethyl C8-10 Alkoxypropylamine Oxide, Dihydroxyethyl C9-1 1 Alkox- ypropylamine Oxide, Dihydroxyethyl C12-15 Alkoxypropylamine Oxide, Dihydroxyethyl Cocamine Oxide, Dihydroxyethyl Lauramine Oxide, Dihydroxyethyl Stearamine Oxide, Dihydroxyethyl Tallowamine Oxide, Dimethicone PEG-7 Phosphate, Dimethicone PEG-10 Phosphate, Dimethicone PEG/PPG-7/4 Phosphate, Dimethicone PEG/PPG- 12/4 Phosphate, Dimethicone/Polyglycerin-3 Crosspolymer, Dimethicone Propyl PG- Betaine, Dimyristyl Phosphate, Dioleoylamidoethyl Hydroxyethylmonium Methosul- fate, DIPA- Hydrogenated Cocoate, DIPA-Lanolate, DIPA-Myristate, Dipotassium Capryloyl Glutamate, Dipotassium Lauryl Sulfosuccinate, Dipotassium Undecylenoyl Glutamate, Disodium Babassuamido MEA-Sulfosuccinate, Disodium Caproamphodi- acetate, Disodium Caproamphodipropionate, Disodium Capryloamphodiacetate, Diso- dium Capryloamphodipropionate, Disodium Capryloyl Glutamate, Disodium Cetearyl Sulfosuccinate, Disodium Cetyl Phenyl Ether Disulfonate, Disodium Cetyl Sulfosuccin- ate, Disodium Cocamido MEA-Sulfosuccinate, Disodium Cocamido MIPA PEG-4 Sul- fosuccinate, Disodium Cocamido MIPA-Sulfosuccinate, Disodium Cocamido PEG-3 Sulfosuccinate, Disodium Coceth-3 Sulfosuccinate, Disodium Cocoamphocarboxyeth- ylhydroxypropylsulfonate, Disodium Cocoamphodiacetate, Disodium Cocoamphodi- propionate, Disodium Coco-Glucoside Sulfosuccinate, Disodium Coco-Sulfosuccinate, Disodium Cocoyl Butyl Gluceth-10 Sulfosuccinate, Disodium Cocoyl Glutamate, Diso- dium C12-14 Pareth-1 Sulfosuccinate, Disodium C12-14 Pareth-2 Sulfosuccinate, Disodium C12-15 Pareth Sulfosuccinate, Disodium C12-14 Sec-Pareth-3 Sulfosuccin- ate, Disodium C12-14 Sec-Pareth-5 Sulfosuccinate, Disodium C12-14 Sec-Pareth-7 Sulfosuccinate, Disodium C12-14 Sec-Pareth-9 Sulfosuccinate, Disodium C12-14 Sec-Pareth-12 Sulfosuccinate, Disodium Deceth-5 Sulfosuccinate, Disodium Deceth- 6 Sulfosuccinate, Disodium Decyl Phenyl Ether Disulfonate, Disodium Dihydroxyethyl Sulfosuccinylundecylenate, Disodium Ethylene Dicocamide PEG-15 Disulfate, Diso- dium Hydrogenated Cottonseed Glyceride Sulfosuccinate, Disodium Hydrogenated Tallow Glutamate, Disodium Hydroxydecyl Sorbitol Citrate, Disodium Isodecyl Sul- fosuccinate, Disodium Isostearamido MEA-Sulfosuccinate, Disodium Isostearamido MIPA-Sulfosuccinate, Disodium Isostearoamphodiacetate, Disodium Isostearoam- phodipropionate, Disodium Isostearyl Sulfosuccinate, Disodium Laneth-5 Sulfosuccin- ate, Disodium Lauramido MEA-Sulfosuccinate, Disodium Lauramido MIPA Glycol Sul- fosuccinate, Disodium Lauramido PEG-2 Sulfosuccinate, Disodium Lauramido PEG-5 Sulfosuccinate, Disodium Laureth-5 Carboxyamphodiacetate, Disodium Laureth-7 Cit- rate, Disodium Laureth Sulfosuccinate, Disodium Laureth-6 Sulfosuccinate, Disodium Laureth-9 Sulfosuccinate, Disodium Laureth-12 Sulfosuccinate, Disodium Laurimino- bishydroxypropylsulfonate, Disodium Lauriminodiacetate, Disodium Lauriminodipropi- onate, Disodium Lauriminodipropionate Tocopheryl Phosphates, Disodium Lauroam- phodiacetate, Disodium Lauroamphodipropionate, Disodium N- Lauroyl Aspartate, Disodium Lauroyl Glutamate, Disodium Lauryl Phenyl Ether Disulfonate, Disodium Lauryl Sulfosuccinate, Disodium Myristamido MEA-Sulfosuccinate, Disodium Nonox- ynol-10 Sulfosuccinate, Disodium Oleamido MEA-Sulfosuccinate, Disodium Oleamido MIPA-Sulfosuccinate, Disodium Oleamido PEG-2 Sulfosuccinate, Disodium Oleoam- phodipropionate, Disodium Oleth-3 Sulfosuccinate, Disodium Oleyl Phosphate, Diso- dium Oleyl Sulfosuccinate, Disodium Palmitamido PEG-2 Sulfosuccinate, Disodium Palmitoleamido PEG-2 Sulfosuccinate, Disodium PEG-4 Cocamido MIPA-Sulfosuccin- ate, Disodium PEG-12 Dimethicone Sulfosuccinate, Disodium PEG-8 Palm Glycerides Sulfosuccinate, Disodium PPG-2-lsodeceth-7 Carboxyamphodiacetate, Disodium Ric- inoleamido MEA-Sulfosuccinate, Disodium Sitostereth-14 Sulfosuccinate, Disodium Soyamphodiacetate, Disodium Stearamido MEA-Sulfosuccinate, Disodium Stearimi- nodipropionate, Disodium Stearoamphodiacetate, Disodium Stearoyl Glutamate, Diso- dium Stearyl Sulfosuccinamate, Disodium Stearyl Sulfosuccinate, Disodium 2-Sul- folaurate, Disodium 2-Sulfopalmitate, Disodium Tallamido MEA-Sulfosuccinate, Diso- dium Tallowamido MEA-Sulfosuccinate, Disodium Tallowamphodiacetate, Disodium Tallowiminodipropionate, Disodium Tallow Sulfosuccinamate, Disodium Tridecyl- sulfosuccinate, Disodium Undecylenamido MEA-Sulfosuccinate, Disodium Undecyle- namido PEG-2 Sulfosuccinate, Disodium Undecylenoyl Glutamate, Disodium Wheat Germamido MEA-Sulfosuccinate, Disodium Wheat Germamido PEG-2 Sulfosuccin- ate, Disodium Wheatgermamphodiacetate, Di-TEA-Cocamide Diacetate, Di-TEA- Oleamido PEG-2 Sulfosuccinate, Di-TEA-Palmitoyl Aspartate, Ditridecyl Sodium Sul- fosuccinate, Dodecylbenzene Sulfonic Acid, Erucamidopropyl Hydroxysultaine, Ethylhexeth-3 Carboxylic Acid, Ethyl PEG-15 Cocamine Sulfate, Glyceryl Capryl Ether, Hexyldecanoic Acid, Hydrogenated Coconut Acid, Hydrogenated Laneth-25, Hydro- genated Menhaden Acid, Hydrogenated Palm Acid, Hydrogenated Palm Kernel Amine Oxide, Hydrogenated Tallow Acid, Hydrogenated Tallowamine Oxide, Hydrogenated Tallow Betaine, Hydrogenated Talloweth-25, Hydrogenated Tallowoyl Glutamic Acid, Hydrolyzed Candida Bombicola Extract, Hydroxyceteth-60, Hydroxyethyl Acetomo- nium PG-Dimethicone, Hydroxyethylbutylamine Laureth Sulfate, Hydroxyethyl Carbox- ymethyl Cocamidopropylamine, Hydroxyethyl Hydroxypropyl C12-15 Alkoxypropyla- mine Oxide, Hydroxylauryl/Hydroxymyristyl Betaine, Hydroxystearic Acid, Hydroxy- succinimidyl C10-40 Isoalkyl Acidate, Hydroxysuccinimidyl C21 -22 Isoalkyl Acidate, Hydroxysultaines, IPDI/PEG-15 Soyamine Oxide Copolymer, IPDI/PEG-15 Soyetho- nium Ethosulfate Copolymer, IPDI/PEG-15 Soy Glycinate Copolymer, lsoceteth-30, lsolaureth-4 Phosphate, lsopolyglyceryl-3 Dimethicone, lsopolyglyceryl-3 Dimethi- conol, Isopropanolamine Lanolate, Isopropylamine Dodecylbenzenesulfonate, Isos- tearamidopropylamine Oxide, Isostearamidopropyl Betaine, Isostearamidopropyl Mor- pholine Oxide, lsosteareth-8, lsosteareth-16, lsosteareth-22, lsosteareth-25, Isos- teareth-50, Isostearic Acid, Isostearoyl Hydrolyzed Collagen, Jojoba Oil PEG-150 Es- ters, Jojoba Wax PEG-80 Esters, Jojoba Wax PEG-120 Esters, Laneth-20, Laneth-25, Laneth-40, Laneth-50, Laneth-60, Laneth-75, Lanolin Acid, Lauramidopropylamine Oxide, Lauramidopropyl Betaine, Lauramidopropyl Hydroxysultaine, Lauramine Oxide, Lauraminopropionic Acid, Laurdimoniumhydroxypropyl Decylglucosides Chloride, Laurdimoniumhydroxypropyl Laurylglucosides Chloride, Laureth-16, Laureth-20, Lau- reth-21 , Laureth-23, Laureth-25, Laureth-30, Laureth-38, Laureth-40, Laureth-3 Car- boxylic Acid, Laureth-4 Carboxylic Acid, Laureth-5 Carboxylic Acid, Laureth- 6 Carbox- ylic Acid, Laureth-8 Carboxylic Acid, Laureth-10 Carboxylic Acid, Laureth-1 1 Carbox- ylic Acid, Laureth-12 Carboxylic Acid, Laureth-13 Carboxylic Acid, Laureth-14 Carbox- ylic Acid, Laureth-17 Carboxylic Acid, Laureth-6 Citrate, Laureth-7 Citrate, Laureth-1 Phosphate, Laureth-2 Phosphate, Laureth-3 Phosphate, Laureth-4 Phosphate, Lau- reth-7 Phosphate, Laureth-8 Phosphate, Laureth-7 Tartrate, Laurie Acid, Laurimino Bispropanediol, Lauriminodipropionic Acid, Lauroamphodipropionic Acid, Lauroyl Beta-Alanine, Lauroyl Collagen Amino Acids, Lauroyl Ethyltrimonium Methosulfate, Lauroyl Hydrolyzed Collagen, Lauroyl Hydrolyzed Elastin, Lauroyl Methyl Glucamide, Lauroyl Sarcosine, Lauroyl Silk Amino Acids, Lauryl Betaine, Lauryl Dimethicone/Pol- yglycerin-3 Crosspolymer, Lauryldimoniumhydroxypropyl Cocoglucosides Chloride, Lauryl Glucoside, Laurylglucosides Hydroxypropyltrimonium Chloride, Lauryl Glycol Hydroxypropyl Ether, Lauryl Hydroxysultaine, Lauryl Malamide, Lauryl Methylglu- camide, Lauryl/Myristyl Glycol Hydroxypropyl Ether, Lauryl/Myristyl Wheat Bran/Straw Glycosides, Lauryl Polyglyceryl-3 Polydimethylsiloxyethyl Dimethicone, Lauryl Pyrroli- done, Lauryl Sultaine, Linoleic Acid, Linolenic Acid, Linseed Acid, Lysine Cocoate, Macadamia Seed Oil Glycereth-8 Esters, Magnesium Coceth Sulfate, Magnesium Coco-Sulfate, Magnesium Isododecylbenzenesulfonate, Magnesium Laureth-11 Car- boxylate, Magnesium Laureth Sulfate, Magnesium Laureth-5 Sulfate, Magnesium Lau- reth-8 Sulfate, Magnesium Laureth-16 Sulfate, Magnesium Laureth-3 Sulfosuccinate, Magnesium Lauryl Hydroxypropyl Sulfonate, Magnesium Lauryl Sulfate, Magnesium Methyl Cocoyl Taurate, Magnesium Myreth Sulfate, Magnesium Oleth Sulfate, Mag- nesium/TEA-Coco-Sulfate, Manicouagan Clay, MEA-Cocoate, MEA-Laureth-6 Car- boxylate, MEA- Laureth Sulfate, MEA-Lauryl Sulfate, MEA PPG-6 Laureth-7 Carbox- ylate, MEA-PPG-8-Steareth-7 Carboxylate, MEA-Undecylenate, Meroxapol 108, Mer- oxapol 174, Meroxapol 178, Meroxapol 254, Meroxapol 255, Meroxapol 258, Mer- oxapol 314, Methoxy PEG-450 Amidoglutaroyl Succinimide, Methoxy PEG-450 Amido Hydroxysuccinimidyl Succinamate, Methoxy PEG-450 Maleimide, Methyl Morpholine Oxide, Milkamidopropyl Amine Oxide, Milkamidopropyl Betaine, Minkamidopropyla- mine Oxide, Minkamidopropyl Betaine, MIPA C12-15 Pareth Sulfate, MIPA-Do- decylbenzenesulfonate, MIPA-Laureth Sulfate, MIPA-Lauryl Sulfate, Mixed Isopro- panolamines Lanolate, Mixed Isopropanolamines Lauryl Sulfate, Mixed Isopropanola- mines Myristate, Morpholine Oleate, Morpholine Stearate, Myreth-3 Carboxylic Acid, Myreth-5 Carboxylic Acid, Myristalkonium Chloride, Myristamidopropylamine Oxide, Myristamidopropyl Betaine, Myristamidopropyl Dimethylamine Phosphate, Myristami- dopropyl Hydroxysultaine, Myristamidopropyl PG-Dimonium Chloride Phosphate, Myristamine Oxide, Myristaminopropionic Acid, Myristic Acid, Myristoyl Ethyltrimonium Methosulfate, Myristoyl Glutamic Acid, Myristoyl Hydrolyzed Collagen, Myristoyl Sar- cosine, Myristyl Betaine, Myristyl/Cetyl Amine Oxide, Myristyldimoniumhydroxypropyl Cocoglucosides Chloride, Myristyl Glucoside, Myristyl Phosphate, Nonoxynol-20, Non- oxynol-23, Nonoxynol-25, Nonoxynol-30, Nonoxynol-35, Nonoxynol-40, Nonoxynol- 44, Nonoxynol-50, Nonoxynol-100, Nonoxynol-120, Nonoxynol-5 Carboxylic Acid, Nonoxynol-8 Carboxylic Acid, Nonoxynol-10 Carboxylic Acid, Nonoxynol-3 Phosphate, Nonoxynol-4 Phosphate, Nonoxynol-6 Phosphate, Nonoxynol-9 Phosphate, Nonox- ynol-10 Phosphate, Nonyl Nonoxynol-30, Nonyl Nonoxynol-49, Nonyl Nonoxynol-100, Nonyl Nonoxynol-150, Nonyl Nonoxynol-7 Phosphate, Nonyl Nonoxynol-8 Phosphate, Nonyl Nonoxynol-9 Phosphate, Nonyl Nonoxynol-10 Phosphate, Nonyl Nonoxynol-1 1 Phosphate, Nonyl Nonoxynol-15 Phosphate, Nonyl Nonoxynol-24 Phosphate, Oatam- idopropyl Betaine, Octoxynol-16, Octoxynol-25, Octoxynol-30, Octoxynol-33, Oc- toxynol-40, Octoxynol-70, Octoxynol-20 Carboxylic Acid, Octyldodeceth-20, Oc- tyldodeceth-25, Octyldodeceth-30, Oleamidopropylamine Oxide, Oleamidopropyl Betaine, Oleamidopropyl Hydroxysultaine, Oleamine Oxide, Oleic Acid, Oleoyl Hydro- lyzed Collagen, Oleoyl Sarcosine, Oleth-20, Oleth-23, Oleth-24, Oleth-25, Oleth-30, Oleth-35, Oleth-40, Oleth-44, Oleth-50, Oleth-3 Carboxylic Acid, Oleth-6 Carboxylic Acid, Oleth-10 Carboxylic Acid, Oleyl Betaine, Olivamidopropylamine Oxide, Olivami- dopropyl Betaine, Olive Acid, Olivoyl Hydrolyzed Wheat Protein, Ophiopogon Extract Stearate, Ozonized Oleth-10, Ozonized PEG-10 Oleate, Ozonized PEG-14 Oleate, Ozonized Polysorbate 80, Palm Acid, Palmamidopropyl Betaine, Palmeth-2 Phos- phate, Palmitamidopropylamine Oxide, Palmitamidopropyl Betaine, Palmitamine Ox- ide, Palmitic Acid, Palmitoyl Collagen Amino Acids, Palmitoyl Glycine, Palmitoyl Hy- drolyzed Collagen, Palmitoyl Hydrolyzed Milk Protein, Palmitoyl Hydrolyzed Wheat Protein, Palmitoyl Keratin Amino Acids, Palmitoyl Oligopeptide, Palmitoyl Silk Amino Acids, Palm Kernel Acid, Palm Kernelamidopropyl Betaine, Peach Kernel Oil Glycer- eth-8 Esters, Peanut Acid, PEG-10 Castor Oil, PEG-40 Castor Oil, PEG-44 Castor Oil, PEG-50 Castor Oil, PEG-54 Castor Oil, PEG-55 Castor Oil, PEG-60 Castor Oil, PEG- 80 Castor Oil, PEG-100 Castor Oil, PEG-200 Castor Oil, PEG-11 Cocamide, PEG-6 Cocamide Phosphate, PEG-4 Cocamine, PEG-8 Cocamine, PEG-12 Cocamine, PEG- 150 Dibehenate, PEG-90 Diisostearate, PEG-75 Dilaurate, PEG-150 Dilaurate, PEG- 75 Dioleate, PEG-150 Dioleate, PEG-75 Distearate, PEG-120 Distearate, PEG-150 Distearate, PEG-175 Distearate, PEG-190 Distearate, PEG-250 Distearate, PEG-30 Glyceryl Cocoate, PEG-40 Glyceryl Cocoate, PEG-78 Glyceryl Cocoate, PEG-80 Glyc- eryl Cocoate, PEG-30 Glyceryl Isostearate, PEG-40 Glyceryl Isostearate, PEG- 50 Glyceryl Isostearate, PEG-60 Glyceryl Isostearate, PEG-90 Glyceryl Isostearate, PEG-23 Glyceryl Laurate, PEG-30 Glyceryl Laurate, PEG-25 Glyceryl Oleate, PEG-30 Glyceryl Oleate, PEG-30 Glyceryl Soyate, PEG-25 Glyceryl Stearate, PEG-30 Glyceryl Stearate, PEG-40 Glyceryl Stearate, PEG-120 Glyceryl Stearate, PEG-200 Glyceryl Stearate, PEG-28 Glyceryl Tallowate, PEG-80 Glyceryl Tallowate, PEG-82 Glyceryl Tallowate, PEG-130 Glyceryl Tallowate, PEG-200 Glyceryl Tallowate, PEG-45 Hydro- genated Castor Oil, PEG-50 Hydrogenated Castor Oil, PEG-54 Hydrogenated Castor Oil, PEG-55 Hydrogenated Castor Oil, PEG-60 Hydrogenated Castor Oil, PEG-80 Hy- drogenated Castor Oil, PEG-100 Hydrogenated Castor Oil, PEG-200 Hydrogenated Castor Oil, PEG-30 Hydrogenated Lanolin, PEG-70 Hydrogenated Lanolin, PEG-50 Hydrogenated Palmamide, PEG-2 Isostearate, PEG-3 Isostearate, PEG-4 Isostearate, PEG-6 Isostearate, PEG-8 Isostearate, PEG-10 Isostearate, PEG-12 Isostearate, PEG-20 Isostearate, PEG-30 Isostearate, PEG-40 Isostearate, PEG- 26 Jojoba Acid, PEG-40 Jojoba Acid, PEG-15 Jojoba Alcohol, PEG-26 Jojoba Alcohol, PEG-40 Jojoba Alcohol, PEG-35 Lanolin, PEG-40 Lanolin, PEG-50 Lanolin, PEG-55 Lanolin, PEG-60 Lanolin, PEG- 70 Lanolin, PEG-75 Lanolin, PEG-85 Lanolin, PEG-100 Lanolin, PEG- 150 Lanolin, PEG-75 Lanolin Oil, PEG-2 Lauramide, PEG-3 Lauramine Oxide, PEG- 20 Laurate, PEG-32 Laurate, PEG-75 Laurate, PEG-150 Laurate, PEG-70 Mango Gly- cerides, PEG-20 Mannitan Laurate, PEG-8 Methyl Ether Dimethicone, PEG-120 Me- thyl Glucose Dioleate, PEG-80 Methyl Glucose Laurate, PEG-120 Methyl Glucose Tri- oleate, PEG-4 Montanate, PEG-30 Oleamine, PEG-20 Oleate, PEG-23 Oleate, PEG- 32 Oleate, PEG-36 Oleate, PEG-75 Oleate, PEG-150 Oleate, PEG-20 Palmitate, PEG- 150 Polyglyceryl-2 Tristearate, PEG/PPG-28/21 Acetate Dimethicone, PEG/PPG- 24/18 Butyl Ether Dimethicone, PEG/PPG-3/17 Copolymer, PEG/PPG-5/35 Copoly- mer, PEG/PPG-8/55 Copolymer, PEG/PPG-10/30 Copolymer, PEG/PPG-10/65 Co- polymer, PEG/PPG-12/35 Copolymer, PEG/PPG-16/17 Copolymer, PEG/PPG-20/9 Copolymer, PEG/PPG-20/20 Copolymer, PEG/PPG-20/60 Copolymer, PEG/PPG- 20/65 Copolymer, PEG/PPG-22/25 Copolymer, PEG/PPG-28/30 Copolymer, PEG/PPG-30-35 Copolymer, PEG/PPG-30/55 Copolymer, PEG/PPG-35/40 Copoly- mer, PEG/PPG-50/40 Copolymer, PEG/PPG-150/35 Copolymer, PEG/PPG-160/30 Copolymer, PEG/PPG-190/60 Copolymer, PEG/PPG-200/40 Copolymer, PEG/PPG- 300/55 Copolymer, PEG/PPG-20/22 Methyl Ether Dimethicone, PEG-26-PPG-30 Phosphate, PEG/PPG-4/2 Propylheptyl Ether, PEG/PPG-6/2 Propylheptyl Ether, PEG- 7/PPG-2 Propylheptyl Ether, PEG/PPG-8/2 Propylheptyl Ether, PEG/PPG- 10/2 Propylheptyl Ether, PEG/PPG-14/2 Propylheptyl Ether, PEG/PPG-40/2 Propylheptyl Ether, PEG/PPG-10/2 Ricinoleate, PEG/PPG-32/3 Ricinoleate, PEG-55 Propylene Glycol Oleate, PEG-25 Propylene Glycol Stearate, PEG-75 Propylene Glycol Stearate, PEG-120 Propylene Glycol Stearate, PEG-5 Rapeseed Sterol, PEG-10 Rapeseed Sterol, PEG-40 Ricinoleamide, PEG-75 Shea Butter Glycerides, PEG-75 Shorea But- ter Glycerides, PEG-20 Sorbitan Cocoate, PEG-20 Sorbitan Isostearate, PEG-40 Sor- bitan Lanolate, PEG-75 Sorbitan Lanolate, PEG-10 Sorbitan Laurate, PEG-40 Sorbi- tan Laurate, PEG-44 Sorbitan Laurate, PEG-75 Sorbitan Laurate, PEG-80 Sorbitan Laurate, PEG-20 Sorbitan Oleate, PEG-80 Sorbitan Palmitate, PEG-40 Sorbitan Stea- rate, PEG-60 Sorbitan Stearate, PEG-160 Sorbitan Triisostearate, PEG-40 Soy Sterol, PEG-2 Stearamide Carboxylic Acid, PEG-9 Stearamide Carboxylic Acid, PEG-20 Stearate, PEG-23 Stearate, PEG-25 Stearate, PEG-30 Stearate, PEG-32 Stearate, PEG-35 Stearate, PEG-36 Stearate, PEG-40 Stearate, PEG-45 Stearate, PEG-50 Stearate, PEG-55 Stearate, PEG-75 Stearate, PEG-90 Stearate, PEG-100 Stearate, PEG- 120 Stearate, PEG-150 Stearate, PEG-45 Stearate Phosphate, PEG-20 Tallate, PEG-50 Tallow Amide, PEG-2 Tallowamide DEA, PEG-20 Tallowate, PEG-66 Trihy- droxystearin, PEG-200 Trihydroxystearin, PEG-60 Tsubakiate Glycerides, Pelargonic Acid, Pentadoxynol-200, Pheneth-6 Phosphate, Poloxamer 105, Poloxamer 108, Poloxamer 182, Poloxamer 183, Poloxamer 184, Poloxamer 188, Poloxamer 217, Poloxamer 234, Poloxamer 235, Poloxamer 237, Poloxamer 238, Poloxamer 288, Poloxamer 334, Poloxamer 335, Poloxamer 338, Poloxamine 908, Poloxamine 1508, Polydimethylsiloxy PEG/PPG-24/19 Butyl Ether Silsesquioxane, Polydimethylsiloxy PPG-13 Butyl Ether Silsesquioxane, Polyglyceryl-6 Caprate, Polyglyceryl-10 Dilaurate, Polyglyceryl-20 Heptacaprylate, Polyglyceryl-20 Hexacaprylate, Polyglyceryl-2 Lauryl Ether, Polyglyceryl-10 Lauryl Ether, Polyglyceryl-20 Octaisononanoate, Polyglyceryl-6 Pentacaprylate, Polyglyceryl-10 Pentacaprylate, Polyglyceryl-3 Polydimethylsiloxy- ethyl Dimethicone, Polyglyceryl-6 Tetracaprylate, Polyglyceryl-10 Tetralaurate, Poly- glyceryl-6 Tricaprylate, Polyglyceryl-10 Trilaurate, Polyquaternium- 77, Polyquater- nium-78, Polyquaternium-79, Polyquaternium-80, Polyquaternium-81 , Polyquater- nium- 82, Pomaderris Kumerahou Flower/Leaf Extract, Poria Cocos Extract, Potas- sium Abietoyl Hydrolyzed Collagen, Potassium Babassuate, Potassium Behenate, Po- tassium C9-15 Alkyl Phosphate, Potassium C1 1 -15 Alkyl Phosphate, Potassium C12- 13 Alkyl Phosphate, Potassium C12-14 Alkyl Phosphate, Potassium Caprate, Potassium Capryloyl Glutamate, Potassium Capryloyl Hydrolyzed Rice Protein, Potas- sium Castorate, Potassium Cocoate, Potassium Cocoyl Glutamate, Potassium Cocoyl Glycinate, Potassium Cocoyl Hydrolyzed Casein, Potassium Cocoyl Hydrolyzed Col- lagen, Potassium Cocoyl Hydrolyzed Corn Protein, Potassium Cocoyl Hydrolyzed Ker- atin, Potassium Cocoyl Hydrolyzed Oat Protein, Potassium Cocoyl Hydrolyzed Potato Protein, Potassium Cocoyl Hydrolyzed Rice Bran Protein, Potassium Cocoyl Hydro- lyzed Rice Protein, Potassium Cocoyl Hydrolyzed Silk, Potassium Cocoyl Hydrolyzed Soy Protein, Potassium Cocoyl Hydrolyzed Wheat Protein, Potassium Cocoyl Hydro- lyzed Yeast Protein, Potassium Cocoyl PCA, Potassium Cocoyl Sarcosinate, Potas- sium Cocoyl Taurate, Potassium Cornate, Potassium Cyclocarboxypropyloleate, Po- tassium Dihydroxyethyl Cocamine Oxide Phosphate, Potassium Dimethicone PEG-7 Phosphate, Potassium Dodecylbenzenesulfonate, Potassium Hempseedate, Potas- sium Hydrogenated Cocoate, Potassium Hydrogenated Palmate, Potassium Hydro- genated Tallowate, Potassium Hydroxystearate, Potassium Isostearate, Potassium Lanolate, Potassium Laurate, Potassium Laureth-3 Carboxylate, Potassium Laureth-4 Carboxylate, Potassium Laureth-5 Carboxylate, Potassium Laureth-6 Carboxylate, Po- tassium Laureth-10 Carboxylate, Potassium Laureth Phosphate, Potassium Lauroyl Collagen Amino Acids, Potassium Lauroyl Glutamate, Potassium Lauroyl Hydrolyzed Collagen, Potassium Lauroyl Hydrolyzed Pea Protein, Potassium Lauroyl Hydrolyzed Soy Protein, Potassium Lauroyl PCA, Potassium Lauroyl Pea Amino Acids, Potassium Lauroyl Sarcosinate, Potassium Lauroyl Silk Amino Acids, Potassium Lauroyl Wheat Amino Acids, Potassium Lauryl Phosphate, Potassium Lauryl Sulfate, Potassium Li- noleate, Potassium Metaphosphate, Potassium Methyl Cocoyl Taurate, Potassium Myristate, Potassium Myristoyl Glutamate, Potassium Myristoyl Hydrolyzed Collagen, Potassium Octoxynol-12 Phosphate, Potassium Oleate, Potassium Oleoyl Hydrolyzed Collagen, Potassium Olivate, Potassium Olivoyl Hydrolyzed Oat Protein, Potassium Olivoyl Hydrolyzed Wheat Protein, Potassium Olivoyl/Lauroyl Wheat Amino Acids, Po- tassium Olivoyl PCA, Potassium Palmate, Potassium Palmitate, Potassium Palmitoyl Hydrolyzed Corn Protein, Potassium Palmitoyl Hydrolyzed Oat Protein, Potassium Pal- mitoyl Hydrolyzed Rice Protein, Potassium Palmitoyl Hydrolyzed Sweet Almond Pro- tein, Potassium Palmitoyl Hydrolyzed Wheat Protein, Potassium Palm Kernelate, Po- tassium Peanutate, Potassium Rapeseedate, Potassium Ricinoleate, Potassium Saf- flowerate, Potassium Soyate, Potassium Stearate, Potassium Stearoyl Hydrolyzed Collagen, Potassium Tallate, Potassium Tallowate, Potassium Taurate, Potassium Taurine Laurate, Potassium Trideceth-3 Carboxylate, Potassium Trideceth-4 Carbox- ylate, Potassium Trideceth-7 Carboxylate, Potassium Trideceth-15 Carboxylate, Po- tassium Trideceth-19 Carboxylate, Potassium Trideceth-6 Phosphate, Potassium Trideceth-7 Phosphate, Potassium Tsubakiate, Potassium Undecylenate, Potassium Undecylenoyl Hydrolyzed Collagen, Potassium Undecylenoyl Hydrolyzed Rice Pro- tein, PPG-30- Buteth-30, PPG-36-Buteth-36, PPG-38-Buteth-37, PPG-30-Capryleth-4 Phosphate, PPG-10 Cetyl Ether Phosphate, PPG-2 C9-11 Pareth-8, PPG-1 -Deceth- 5, PPG-3-Deceth-2 Carboxylic Acid, PPG-30 Ethylhexeth-4 Phosphate, PPG-20- Glycereth-30, PPG-2 Hydroxyethyl Coco/lsostearamide, PPG-2- lsodeceth-8, PPG-2- lsodeceth-10, PPG-2-lsodeceth-18, PPG-2-lsodeceth-25, PPG-4-lsodeceth-10, Propyltrimonium Hydrolyzed Collagen, Quaternium-24, Quaternium-52, Quaternium- 87, Rapeseed Acid, Rice Bran Acid, Rice Oil Glycereth-8 Esters, Ricinoleamidopropyl Betaine, Ricinoleic Acid, Ricinoleth-40, Safflower Acid, Sapindus Oahuensis Fruit Ex- tract, Saponaria Officinalis Root Powder, Saponins, Sekken-K, Sekken-Na/K, Sekken Soji, Sekken Soji-K, Sesame Oil Glycereth-8 Esters, Sesamidopropylamine Oxide, Sesamidopropyl Betaine, Shea Butteramidopropyl Betaine, Shea Butter Glycereth-8 Esters, Sodium Arachidate, Sodium Arganampohoacetate, Sodium Astrocaryum Murumuruate, Sodium Avocadoate, Sodium Babassuamphoacetate, Sodium Babas- suate, Sodium Babassu Sulfate, Sodium Behenate, Sodium Bisglycol Ricinosulfosuc- cinate, Sodium Bis- Hydroxyethylglycinate Coco-Glucosides Crosspolymer, Sodium Bis-Hydroxyethylglycinate Lauryl- Glucosides Crosspolymer, Sodium Borageami- dopropyl PG-Dimonium Chloride Phosphate, Sodium Butoxynol-12 Sulfate, Sodium Butylglucosides Hydroxypropyl Phosphate, Sodium C13-17 Alkane Sulfonate, Sodium C14-18 Alkane Sulfonate, Sodium C12-15 Alkoxypropyl Iminodipropionate, Sodium C10-16 Alkyl Sulfate, Sodium C1 1 -15 Alkyl Sulfate, Sodium C12-13 Alkyl Sulfate, So- dium C12-15 Alkyl Sulfate, Sodium C12-18 Alkyl Sulfate, Sodium C16-20 Alkyl Sulfate, Sodium C9-22 Alkyl Sec Sulfonate, Sodium C14-17 Alkyl Sec Sulfonate, Sodium Caprate, Sodium Caproamphoacetate, Sodium Caproamphohydroxypropylsulfonate, Sodium Caproamphopropionate, Sodium Caproyl Methyltaurate, Sodium Caprylate, Sodium Capryleth-2 Carboxylate, Sodium Capryleth-9 Carboxylate, Sodium Caprylo- amphoacetate, Sodium Capryloamphohydroxypropylsulfonate, Sodium Capryloam- phopropionate, Sodium Capryloyl Glutamate, Sodium Capryloyl Hydrolyzed Wheat Protein, Sodium Caprylyl PG-Sulfonate, Sodium Caprylyl Sulfonate, Sodium Castor- ate, Sodium Ceteareth-13 Carboxylate, Sodium Cetearyl Sulfate, Sodium Ceteth-13 Carboxylate, Sodium Cetyl Sulfate, Sodium Cocamidopropyl PG-Dimonium Chloride Phosphate, Sodium Cocaminopropionate, Sodium Coceth Sulfate, Sodium Coceth-30 Sulfate, Sodium Cocoabutteramphoacetate, Sodium Cocoa Butterate, Sodium Co- coamphoacetate, Sodium Cocoamphohydroxypropylsulfonate, Sodium Cocoampho- propionate, Sodium Cocoate, Sodium Coco/Babassu/Andiroba Sulfate, So- dium Coco/Babassu Sulfate, Sodium Cocoglucosides Hydroxypropyl Phosphate, So- dium Cocoglucosides Hydroxypropylsulfonate, Sodium Coco-Glucoside Tartrate, So- dium Cocoglyceryl Ether Sulfonate, Sodium Coco/Hydrogenated Tallow Sulfate, So- dium Cocoiminodiacetate, Sodium Cocomonoglyceride Sulfate, Sodium Cocomono- glyceride Sulfonate, Sodium Coco PG-Dimonium Chloride Phosphate, Sodium Coco- Sulfate, Sodium Coco Sulfoacetate, Sodium Cocoyl Alaninate, Sodium Cocoyl Amino Acids, Sodium Cocoyl Collagen Amino Acids, Sodium Cocoyl Glutamate, Sodium Co- coyl Glutaminate, Sodium Cocoyl Glycinate, Sodium Cocoyl/Hydrogenated Tallow Glu- tamate, Sodium Cocoyl Hydrolyzed Collagen, Sodium Cocoyl Hydrolyzed Keratin, So- dium Cocoyl Hydrolyzed Rice Protein, Sodium Cocoyl Hydrolyzed Silk, Sodium Cocoyl Hydrolyzed Soy Protein, Sodium Cocoyl Hydrolyzed Sweet Almond Protein, Sodium Cocoyl Hydrolyzed Wheat Protein, Sodium Cocoyl Hydrolyzed Wheat Protein Gluta- mate, Sodium Cocoyl Isethionate, Sodium Cocoyl Methylaminopropionate, Sodium Cocoyl Oat Amino Acids, Sodium Cocoyl/Palmoyl/Sunfloweroyl Glutamate, Sodium Cocoyl Proline, Sodium Cocoyl Sarcosinate, Sodium Cocoyl Taurate, Sodium Cocoyl Threoninate, Sodium Cocoyl Wheat Amino Acids, Sodium C12-14 Olefin Sulfonate, Sodium C14-16 Olefin Sulfonate, Sodium C14- 18 Olefin Sulfonate, Sodium C16-18 Olefin Sulfonate, Sodium Cornamphopropionate, Sodium Cottonseedamphoacetate, Sodium C13-15 Pareth-8 Butyl Phosphate, Sodium C9-1 1 Pareth-6 Carboxylate, So- dium C1 1 -15 Pareth-7 Carboxylate, Sodium C12-13 Pareth-5 Carboxylate, Sodium C12-13 Pareth-8 Carboxylate, Sodium C12-13 Pareth-12 Carboxylate, Sodium C12- 15 Pareth-6 Carboxylate, Sodium C12-15 Pareth-7 Carboxylate, Sodium C12-15 Pa- reth-8 Carboxylate, Sodium C14-15 Pareth-8 Carboxylate, Sodium C12-14 Sec-Pa- reth-8 Carboxylate, Sodium C14-15 Pareth-PG Sulfonate, Sodium C12-13 Pareth-2 Phosphate, Sodium C13-15 Pareth-8 Phosphate, Sodium C9-15 Pareth-3 Sulfate, So- dium C10-15 Pareth Sulfate, Sodium C10-16 Pareth-2 Sulfate, Sodium C12-13 Pareth Sulfate, Sodium C12-15 Pareth Sulfate, Sodium C12-15 Pareth-3 Sulfate, Sodium C13-15 Pareth-3 Sulfate, Sodium C12-14 Sec-Pareth-3 Sulfate, Sodium C12-15 Pa- reth-3 Sulfonate, Sodium C12-15 Pareth-7 Sulfonate, Sodium C12-15 Pareth-15 Sul- fonate, Sodium Deceth-2 Carboxylate, Sodium Deceth Sulfate, Sodium Decylben- zenesulfonate, Sodium Decylglucosides Hydroxypropyl Phosphate, Sodium Decylglu- cosides Hydroxypropylsulfonate, Sodium Dilaureth-7 Citrate, Sodium Dilaureth-10 Phosphate, Sodium Dilinoleamidopropyl PG-Dimonium Chloride Phosphate, Sodium Dilinoleate, Sodium Dioleth-8 Phosphate, Sodium Dodecylbenzenesulfonate, Sodium Ethyl 2- Sulfolaurate, Sodium Glyceryl Oleate Phosphate, Sodium Grapeseedami- dopropyl PG-Dimonium Chloride Phosphate, Sodium Grapeseedamphoacetate, So- dium Grapeseedate, Sodium Hempseedamphoacetate, Sodium Hexeth-4 Carbox- ylate, Sodium Hydrogenated Cocoate, Sodium Hydrogenated Cocoyl Methyl Isethio- nate, Sodium Hydrogenated Palmate, Sodium Hydrogenated Tallowate, Sodium Hy- drogenated Tallowoyl Glutamate, Sodium Hydroxylauryldimonium Ethyl Phosphate, Sodium Hydroxypropyl Palm Kernelate Sulfonate, Sodium Hydroxypropylphosphate Decylglucoside Crosspolymer, Sodium Hydroxypropylphosphate Laurylglucoside Crosspolymer, Sodium Hydroxypropylsulfonate Cocoglucoside Crosspolymer, Sodium Hydroxypropylsulfonate Decylglucoside Crosspolymer, Sodium Hydroxypropyl- sulfonate Laurylglucoside Crosspolymer, Sodium Hydroxystearate, Sodium Isos- tearate, Sodium lsosteareth-6 Carboxylate, Sodium Isosteareth- 1 1 Carboxylate, So- dium Isostearoamphoacetate, Sodium Isostearoamphopropionate, Sodium N- Isos- tearoyl Methyltaurate, Sodium Laneth Sulfate, Sodium Lanolate, Sodium Lardate, So- dium Lauramido Diacetate, Sodium Lauraminopropionate, Sodium Laurate, Sodium Laureth-3 Carboxylate, Sodium Laureth-4 Carboxylate, Sodium Laureth-5 Carbox- ylate, Sodium Laureth-6 Carboxylate, Sodium Laureth-8 Carboxylate, Sodium Laureth- 11 Carboxylate, Sodium Laureth-12 Carboxylate, Sodium Laureth-13 Carboxylate, So- dium Laureth-14 Carboxylate, Sodium Laureth-16 Carboxylate, Sodium Laureth-17 Carboxylate, Sodium Laureth Sulfate, Sodium Laureth-5 Sulfate, Sodium Laureth- 7 Sulfate, Sodium Laureth-8 Sulfate, Sodium Laureth-12 Sulfate, Sodium Laureth-40 Sulfate, Sodium Laureth-7 Tartrate, Sodium Lauriminodipropionate, Sodium Lauroam- phoacetate, Sodium Lauroamphohydroxypropylsulfonate, Sodium Lauroampho PG- Acetate Phosphate, Sodium Lauroamphopropionate, Sodium Lauroyl Aspartate, So- dium Lauroyl Collagen Amino Acids, Sodium Lauroyl Glycine Propionate, Sodium Lauroyl Hydrolyzed Collagen, Sodium Lauroyl Hydrolyzed Silk, Sodium Lauroyl Hy- droxypropyl Sulfonate, Sodium Lauroyl Isethionate, Sodium Lauroyl Methyla- minopropionate, Sodium Lauroyl Methyl Isethionate, Sodium Lauroyl Millet Amino Ac- ids, Sodium Lauroyl/Myristoyl Aspartate, Sodium Lauroyl Oat Amino Acids, Sodium Lauroyl Sarcosinate, Sodium Lauroyl Silk Amino Acids, Sodium Lauroyl Taurate, So- dium Lauroyl Wheat Amino Acids, Sodium Lauryl Diethylenediaminoglycinate, Sodium Lauryl Glucose Carboxylate, Sodium Laurylglucosides Hydroxypropyl Phosphate, So- dium Laurylglucosides Hydroxypropylsulfonate, Sodium Lauryl Glycol Carboxylate, Sodium Lauryl Hydroxyacetamide Sulfate, Sodium Lauryl Phosphate, Sodium Lauryl Sulfate, Sodium Lauryl Sulfoacetate, Sodium Linoleate, Sodium Macadamiaseedate, Sodium Mangoamphoacetate, Sodium Mangoseedate, Sodium/MEA Laureth-2 Sul- fosuccinate, Sodium Methoxy PPG-2 Acetate, Sodium Methyl Cocoyl Taurate, Sodium Methyl Lauroyl Taurate, Sodium Methyl Myristoyl Taurate, Sodium Methyl Oleoyl Tau- rate, Sodium Methyl Palmitoyl Taurate, Sodium Methyl Stearoyl Taurate, Sodium Me- thyl 2-Sulfolaurate, Sodium Methyl 2- Sulfopalmitate, Sodium Methyltaurate Isopal- mitamide, Sodium Methyltaurine Cocoyl Methyltaurate, Sodium Myreth Sulfate, So- dium Myristate, Sodium Myristoamphoacetate, Sodium Myristoyl Glutamate, Sodium Myristoyl Hydrolyzed Collagen, Sodium Myristoyl Isethionate, Sodium Myristoyl Sar- cosinate, Sodium Myristyl Sulfate, Sodium Nonoxynol-6 Phosphate, Sodium Nonox- ynol-9 Phosphate, Sodium Nonoxynol-1 Sulfate, Sodium Nonoxynol-3 Sulfate, Sodium Nonoxynol-4 Sulfate, Sodium Nonoxynol-6 Sulfate, Sodium Nonoxynol-8 Sulfate, So- dium Nonoxynol-10 Sulfate, Sodium Nonoxynol-25 Sulfate, Sodium Octoxynol-2 Ethane Sulfonate, Sodium Octoxynol-2 Sulfate, Sodium Octoxynol-6 Sulfate, Sodium Octoxynol-9 Sulfate, Sodium Oleate, Sodium Oleoamphoacetate, Sodium Oleoam- phohydroxypropylsulfonate, Sodium Oleoamphopropionate, Sodium Oleoyl Hydro- lyzed Collagen, Sodium Oleoyl Isethionate, Sodium Oleth Sulfate, Sodium Oleyl Me- thyl Isethionate, Sodium Oleyl Sulfate, Sodium Olivamphoacetate, Sodium Olivate, So- dium Olivoyl Glutamate, Sodium Palmamphoacetate, Sodium Palmate, Sodium Palm Glyceride Sulfonate, Sodium Palmitate, Sodium Palmitoyl Hydrolyzed Collagen, So- dium Palmitoyl Hydrolyzed Wheat Protein, Sodium Palmitoyl Sarcosinate, Sodium Palm Kernelate, Sodium Palm Kerneloyl Isethionate, Sodium Palmoyl Glutamate, So- dium Passiflora Edulis Seedate, Sodium Peanutamphoacetate, Sodium Peanutate, Sodium PEG-6 Cocamide Carboxylate, Sodium PEG-8 Cocamide Carboxylate, So- dium PEG-4 Cocamide Sulfate, Sodium PEG-3 Lauramide Carboxylate, Sodium PEG- 4 Lauramide Carboxylate, Sodium PEG-8 Palm Glycerides Carboxylate, Sodium Pen- taerythrityl Hydroxypropyl Iminodiacetate Dendrimer, Sodium Propoxy PPG-2 Acetate, Sodium Rapeseedate, Sodium Ricebranamphoacetate, Sodium Ricinoleate, Sodium Ricinoleoamphoacetate, Sodium Rose Hipsamphoacetate, Sodium Rosinate, Sodium Safflowerate, Sodium Saffloweroyl Hydrolyzed Soy Protein, Sodium Sesameseedate, Sodium Sesamphoacetate, Sodium Sheabutteramphoacetate, Sodium Soyate, So- dium Soy Hydrolyzed Collagen, Sodium Stearate, Sodium Stearoamphoacetate, So- dium Stearoamphohydroxypropylsulfonate, Sodium Stearoamphopropionate, Sodium Stearoyl Casein, Sodium Stearoyl Glutamate, Sodium Stearoyl Hyaluronate, Sodium Stearoyl Hydrolyzed Collagen, Sodium Stearoyl Hydrolyzed Corn Protein, Sodium Stearoyl Hydrolyzed Silk, Sodium Stearoyl Hydrolyzed Soy Protein, Sodium Stearoyl Hydrolyzed Wheat Protein, Sodium Stearoyl Lactalbumin, Sodium Stearoyl Methyl Isethionate, Sodium Stearoyl Oat Protein, Sodium Stearoyl Pea Protein, Sodium Stea- royl Soy Protein, Sodium Stearyl Dimethyl Glycine, Sodium Stearyl Sulfate, Sodium Sunflowerseedamphoacetate, Sodium Surfactin, Sodium Sweetalmondamphoacetate, Sodium Sweet Almondate, Sodium Tallamphopropionate, Sodium Tallate, Sodium Tal- lowamphoacetate, Sodium Tallowate, Sodium Tallow Sulfate, Sodium Tamanuseed- ate, Sodium Taurate, Sodium Taurine Cocoyl Methyltaurate, Sodium Taurine Laurate, Sodium/TEA-Lauroyl Collagen Amino Acids, Sodium/TEA-Lauroyl Hydrolyzed Colla- gen, Sodium/TEA-Lauroyl Hydrolyzed Keratin, Sodium/TEA- Lauroyl Keratin Amino Acids, Sodium/TEA-Undecylenoyl Collagen Amino Acids, Sodium/TEA- Undecylenoyl Hydrolyzed Collagen, Sodium/TEA-Undecylenoyl Hydrolyzed Corn Protein, So- dium/TEA-Undecylenoyl Hydrolyzed Soy Protein, Sodium/TEA-Undecylenoyl Hydro- lyzed Wheat Protein, Sodium Theobroma Grandiflorum Seedate, Sodium Trideceth-3 Carboxylate, Sodium Trideceth-4 Carboxylate, Sodium Trideceth-6 Carboxylate, So- dium Trideceth-7 Carboxylate, Sodium Trideceth-8 Carboxylate, Sodium Trideceth-12 Carboxylate, Sodium Trideceth-15 Carboxylate, Sodium Trideceth-19 Carboxylate, Sodium Trideceth Sulfate, Sodium Tridecylbenzenesulfonate, Sodium Tridecyl Sulfate, Sodium Trimethylolpropane Hydroxypropyl Iminodiacetate Dendrimer, Sodium Unde- ceth-5 Carboxylate, Sodium Undecylenate, Sodium Undecylenoamphoacetate, So- dium Undecylenoamphopropionate, Sodium Undecylenoyl Glutamate, Sodium Wheat Germamphoacetate, Sorbeth-160 Tristearate, Soy Acid, Soyamidopropylamine Oxide, Soyamidopropyl Betaine, Soybean Oil Glycereth-8 Esters, Stearamidopropylamine Oxide, Stearamidopropyl Betaine, Stearamine Oxide, Steareth-15, Steareth-16, Stea- reth-20, Steareth-21 , Steareth-25, Steareth-27, Steareth-30, Steareth- 40, Steareth- 50, Steareth-80, Steareth-100, Steareth-2 Phosphate, Steareth-3 Phosphate, Stearic Acid, Stearoxypropyltrimonium Chloride, Stearoyl Glutamic Acid, Stearoyl Sarcosine, Stearyl Betaine, Stearyldimoniumhydroxypropyl Butylglucosides Chloride, Stearyl- dimoniumhydroxypropyl Decylglucosides Chloride, Stearyldimoniumhydroxypropyl Laurylglucosides Chloride, Sulfated Castor Oil, Sulfated Coconut Oil, Sulfated Glyceryl Oleate, Sulfated Olive Oil, Sulfated Peanut Oil, Sunfloweramide MEA, Sunflower Seed Acid, Sunflowerseedamidopropyl Hydroxyethyldimonium Chloride, Sunflower Seed Oil Glycereth-8 Esters, Tall Oil Acid, Tallow Acid, Tallowamidopropylamine Oxide, Tal- lowamidopropyl Betaine, Tallowamidopropyl Hydroxysultaine, Tallowamine Oxide, Tallow Betaine, Tallow Dihydroxyethyl Betaine, Tallowoyl Ethyl Glucoside, TEA- Abietoyl Hydrolyzed Collagen, TEA-C12-14 Alkyl Phosphate, TEA-C10-15 Alkyl Sul- fate, TEA-C1 1 -15 Alkyl Sulfate, TEA- C12-13 Alkyl Sulfate, TEA-C12-14 Alkyl Sulfate, TEA-C12-15 Alkyl Sulfate, TEA C14-17 Alkyl Sec Sulfonate, TEA-Canolate, TEA-Co- camide Diacetate, TEA-Cocoate, TEA-Coco-Sulfate, TEA-Cocoyl Alaninate, TEA-Co- coyl Glutamate, TEA-Cocoyl Glutaminate, TEA-Cocoyl Glycinate, TEA-Cocoyl Hydro- lyzed Collagen, TEA-Cocoyl Hydrolyzed Soy Protein, TEA-Cocoyl Sarcosinate, TEA- Dimethicone PEG-7 Phosphate, TEA-Dodecylbenzenesulfonate, TEA-Hydrogenated Cocoate, TEA- Hydrogenated Tallowoyl Glutamate, TEA-lsostearate, TEA-lsostearoyl Hydrolyzed Collagen, TEA- Lauraminopropionate, TEA-Laurate, TEA- Laurate/Myristate, TEA-Laureth Sulfate, TEA-Lauroyl Collagen Amino Acids, TEA- Lauroyl Glutamate, TEA-Lauroyl Hydrolyzed Collagen, TEA-Lauroyl Keratin Amino Ac- ids, TEA-Lauroyl Methylaminopropionate, TEA-Lauroyl/Myristoyl Aspartate, TEA- Lau- royl Sarcosinate, TEA-Lauryl Phosphate, TEA-Lauryl Sulfate, TEA-Myristaminopropi- onate, TEA- Myristate, TEA-Myristoyl Hydrolyzed Collagen, TEA-Oleate, TEA-Oleoyl Hydrolyzed Collagen, TEA- Oleoyl Sarcosinate, TEA-Oleyl Sulfate, TEA-Palmitate, TEA-Palm Kernel Sarcosinate, TEA-PEG-3 Cocamide Sulfate, TEA-Rosinate, TEA- Stearate, TEA-Tallate, TEA-T ridecylbenzenesulfonate, TEA- Undecylenate, TEA-Un- decylenoyl Hydrolyzed Collagen, Tetramethyl Decynediol, Tetrasodium Dicarboxy- ethyl Stearyl Sulfosuccinamate, TIPA-Laureth Sulfate, TIPA-Lauryl Sulfate, TIPA- Myristate, TIPA-Stearate, Tocopheryl Phosphate, Trehalose Undecylenoate, TM-C12- 15 Pareth-2 Phosphate, TM-C12-15 Pareth-6 Phosphate, TM-C12-15 Pareth-8 Phos- phate, TM-C12-15 Pareth-10 Phosphate, Trideceth-20, Trideceth-50, Trideceth-3 Car- boxylic Acid, Trideceth-4 Carboxylic Acid, Trideceth-7 Carboxylic Acid, Trideceth-8 Carboxylic Acid, Trideceth-15 Carboxylic Acid, Trideceth-19 Carboxylic Acid, Tride- ceth-10 Phosphate, Tridecylbenzenesulfonic Acid, Trilaureth-9 Citrate, Trimethylolpro- pane Hydroxypropyl Bis-Hydroxyethylamine Dendrimer, Trisodium Lauroampho PG- Acetate Chloride Phosphate, Undecanoic Acid, Undeceth-5 Carboxylic Acid, Un- decylenamidopropylamine Oxide, Undecylenamidopropyl Betaine, Undecylenic Acid, Undecylenoyl Collagen Amino Acids, Undecylenoyl Glycine, Undecylenoyl Hydrolyzed Collagen, Undecylenoyl Wheat Amino Acids, Undecyl Glucoside, Wheat Germ Acid, Wheat Germamidopropylamine Oxide, Wheat Germamidopropyl Betaine, Yucca Schi- digera Leaf/Root/Stem Extract, Yucca Schidigera Stem Extract, Zinc Coceth Sulfatea and Zinc Coco-Sulfate.
[0083] Preferred are one or more compounds selected from the group consisting of Sodium Laureth Sulfate, Cocamidopropyl Betaine, Sodium Cocoamphoacetate, Co- coGlucoside and Ammonium Lauryl Sulfosuccinate.
[0084] The percentage content of surfactants in the preparations may be from 0.1 to 10% by weight and is preferably from 0.5 to 5% by weight, based on the preparation.
Oil bodies
[0085] Suitable oil bodies, which form constituents of the O/W emulsions, are, for ex- ample, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of linear C6-C22-fatty acids with linear or branched C6-C22-fatty alcohols or esters of branched C6-C 13-carboxylic acids with linear or branched C6-C 22- fatty alcohols, such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate, isostearyl palmi- tate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl oleate, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl stearate, behenyl isostearate, behenyl oleate, behenyl behenate, behenyl erucate, erucyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate, erucyl behenate and erucyl erucate. Also suitable are esters of linear C6-C22-fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of C18-C38- alkylhydroxy carboxylic acids with linear or branched C6-C22-fatty alcohols, in particular Dioctyl Mal- ate, esters of linear and/or branched fatty acids with polyhydric alcohols (such as, for example, propylene glycol, dimerdiol or trimertriol) and/or Guerbet alcohols, triglycer- ides based on C6 -C10-fatty acids, liquid mono-/di-/triglyceride mixtures based on C6-C10-fatty acids, esters of C6- C22-fatty alcohols and/or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C2- C12-dicarboxylic acids with linear or branched alcohols having 1 to 22 carbon atoms or polyols having 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C6-C22-fatty alcohol carbonates, such as, for example, Dicaprylyl Carbonate (Cetiol® CC), Guerbet carbonates, based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of benzoic acid with linear and/or branched C6-C22-alcohols (e.g. Finsolv® TN), linear or branched, symmetrical or asymmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group, such as, for example, dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicones, silicone methi- cone grades, etc.) and/or aliphatic or naphthenic hydrocarbons, such as, for example, squalane, squalene or dialkylcyclohexanes.
Emulsifiers
[0086] Other non-ionic or cationic surfactants may also be added to the preparations as emulsifiers, including for example:
• products of the Addition of 2 to 30 mol ethylene oxide and/or 0 to 5 mol propylene oxide onto linear C8-22 fatty alcohols, onto C12-22 fatty acids and onto alkyl phenols containing 8 to 15 carbon atoms in the alkyl group;
• C12/18 fatty acid monoesters and diesters of Addition products of 1 to 30 mol eth- ylene oxide onto glycerol;
• glycerol mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated fatty acids containing 6 to 22 carbon atoms and ethylene oxide Ad- dition products thereof;
• Addition products of 15 to 60 mol ethylene oxide onto castor oil and/or hydrogen- ated castor oil;
• polyol esters and, in particular, polyglycerol esters such as, for example, polygly- cerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol di- merate isostearate. Mixtures of compounds from several of these classes are also suitable; • Addition products of 2 to 15 mol ethylene oxide onto castor oil and/or hydrogen- ated castor oil;
• partial esters based on linear, branched, unsaturated or saturated C6/22 fatty ac- ids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentae- rythritol, dipentaerythritol, sugar alcohols (for example sorbitol), alkyl glucosides (for example methyl glucoside, butyl glucoside, lauryl glucoside) and polygluco- sides (for example cellulose);
• mono-, di and trialkyl phosphates and mono-, di- and/or tri-PEG-alkyl phosphates and salts thereof;
• wool wax alcohols;
• polysiloxane/polyalkyl polyether copolymers and corresponding derivatives;
• mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol and/or mixed esters of C6-22 fatty acids, methyl glucose and polyols, preferably glycerol or polyglycerol,
• polyalkylene glycols and
• glycerol carbonate.
[0087] The Addition products of ethylene oxide and/or propylene oxide onto fatty alco- hols, fatty acids, alkylphenols, glycerol mono- and diesters and sorbitan mono- and diesters of fatty acids or onto castor oil are known commercially available products. They are homologue mixtures of which the average degree of alkoxylation corresponds to the ratio between the quantities of ethylene oxide and/or propylene oxide and sub- strate with which the Addition reaction is carried out. C12/18 fatty acid monoesters and diesters of Addition products of ethylene oxide onto glycerol are known as lipid layer enhancers for cosmetic formulations. The preferred emulsifiers are described in more detail as follows:
[0088] Partial glycerides. Typical examples of suitable partial glycerides are hy- droxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid monoglyceride, isostearic acid diglyceride, oleic acid monoglyceride, oleic acid diglyc- eride, ricinoleic acid monoglyceride, ricinoleic acid diglyceride, linoleic acid mono- glyceride, linoleic acid diglyceride, linolenic acid monoglyceride, linolenic acid diglyc- eride, erucic acid monoglyceride, erucic acid diglyceride, tartaric acid monoglyceride, tartaric acid diglyceride, citric acid monoglyceride, citric acid diglyceride, malic acid monoglyceride, malic acid diglyceride and technical mixtures thereof which may still contain small quantities of triglyceride from the production process. Addition products of 1 to 30 mol and preferably 5 to 10 mol ethylene oxide onto the partial glycerides mentioned are also suitable.
[0089] Sorbitan esters. Suitable sorbitan esters are sorbitan monoisostearate, sorbi- tan sesquiisostearate, sorbitan diisostearate, sorbitan triisostearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate, sorbitan mo- noerucate, sorbitan sesquierucate, sorbitan dierucate, sorbitan trierucate, sorbitan monoricinoleate, sorbitan sesquiricinoleate, sorbitan diricinoleate, sorbitan triricinole- ate, sorbitan monohydroxystearate, sorbitan sesquihydroxystearate, sorbitan dihy- droxystearate, sorbitan trihydroxystearate, sorbitan monotartrate, sorbitan sesquitar- trate, sorbitan ditartrate, sorbitan tritartrate, sorbitan monocitrate, sorbitan ses- quicitrate, sorbitan dicitrate, sorbitan tricitrate, sorbitan monomaleate, sorbitan sesqui- maleate, sorbitan dimaleate, sorbitan trimaleate and technical mixtures thereof. Addi- tion products of 1 to 30 mol and preferably 5 to 10 mol ethylene oxide onto the sorbitan esters mentioned are also suitable.
[0090] Polyglycerol esters. Typical examples of suitable polyglycerol esters are Pol- yglyceryl-2 Dipolyhydroxystearate (Dehymuls® PG PH), Polyglycerin-3-Diisostearate (Lameform® TGI), Polyglyceryl-4 Isostearate (Isolan® Gl 34), Polyglyceryl-3 Oleate, Diisostearoyl Polyglyceryl-3 Diisostearate (Isolan® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care® 450), Polyglyceryl-3 Beeswax (Cera Beilina®), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010/90), Polyglyceryl-3 Cetyl Ether (Chimexane® NL), Polyglyceryl-3 Distearate (Cremophor® GS 32) and Polyglyceryl Polyricinoleate (Admul® WOL 1403), Polyglyceryl Dimerate Isostearate and mixtures thereof. Exam- ples of other suitable polyolesters are the mono-, di- and triesters of trimethylol pro- pane or pentaerythritol with lauric acid, cocofatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like optionally reacted with 1 to 30 mol ethylene oxide.
[0091] Tetraalkyl ammonium salts. Cationically active surfactants comprise the hydrophobic high molecular group required for the surface activity in the cation by dissociation in aqueous solution. A group of important representatives of the cationic surfactants are the tetraalk(en)yl ammonium salts of the general formula: (R1 R2R3R4N+) X-. Here R1 stands for C1-C8 alk(en)yl, R2, R3 and R4, independently of each other, for alk(en)yl groups having 1 to 22 carbon atoms. X is a counter ion, preferably selected from the group of the halides, alkyl sulfates and alkyl carbonates. Cationic surfactants, in which the nitrogen group is substituted with two long acyl groups and two short alk(en)yl groups, are particularly preferred.
[0092] Esterquats. A further class of cationic surfactants particularly useful as co- surfactants for the present invention is represented by the so-called esterquats. Esterquats are generally understood to be quaternised fatty acid triethanolamine ester salts. These are known compounds which can be obtained by the relevant methods of preparative organic chemistry. Reference is made in this connection to International patent application WO 91/01295 A1 , according to which triethanolamine is partly esterified with fatty acids in the presence of hypophosphorous acid, air is passed through the reaction mixture and the whole is then quaternised with dimethyl sulphate or ethylene oxide. In Addition, German patent DE 4308794 C1 describes a process for the production of solid esterquats in which the quaternisation of triethanolamine esters is carried out in the presence of suitable dispersants, preferably fatty alcohols. [0093] Typical examples of esterquats suitable for use in accordance with the invention are products of which the acyl component derives from monocarboxylic acids corresponding to formula RCOOH in which RCO is an acyl group containing 6 to 10 carbon atoms, and the amine component is triethanolamine (TEA). Examples of such monocarboxylic acids are caproic acid, caprylic acid, capric acid and technical mixtures thereof such as, for example, so-called head-fractionated fatty acid. Esterquats of which the acyl component derives from monocarboxylic acids containing 8 to 10 carbon atoms, are preferably used. Other esterquats are those of which the acyl component derives from dicarboxylic acids like malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, sorbic acid, pimelic acid, azelaic acid, sebacic acid and/or dodecanedioic acid, but preferably adipic acid. Overall, esterquats of which the acyl component derives from mixtures of monocarboxylic acids containing 6 to 22 carbon atoms, and adipic acid are preferably used. The molar ratio of mono and dicarboxylic acids in the final esterquat may be in the range from 1 :99 to 99:1 and is preferably in the range from 50:50 to 90:10 and more particularly in the range from 70:30 to 80:20. Besides the quaternised fatty acid triethanolamine ester salts, other suitable esterquats are quaternized ester salts of mono-/dicarboxylic acid mixtures with diethanolalkyamines or 1 ,2-dihydroxypropyl dialkylamines. The esterquats may be obtained both from fatty acids and from the corresponding triglycerides in admixture with the corresponding dicarboxylic acids. One such process, which is intended to be representative of the relevant prior art, is proposed in European patent EP 0750606 B1. To produce the quaternised esters, the mixtures of mono- and dicarboxylic acids and the triethanolamine - based on the available carboxyl functions - may be used in a molar ratio of 1 .1 :1 to 3:1 . With the performance properties of the esterquats in mind, a ratio of 1.2:1 to 2.2:1 and preferably 1.5:1 to 1.9:1 has proved to be particularly advantageous. The preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1 .5 to 1 .9.
Superfatting agents and consistency factors
[0094] Superfatting agents may be selected from such substances as, for example, lanolin and lecithin and also polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the fatty acid alkanolamides also serving as foam stabilizers.
[0095] The consistency factors mainly used are fatty alcohols or hydroxyfatty alcohols containing 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycerides, fatty acids or hydroxyfatty acids. A combination of these substances with alkyl oli- goglucosides and/or fatty acid N-methyl glucamides of the same chain length and/or polyglycerol poly-12-hydroxystearates is preferably used. Thickening agents and rheology additives
[0096] Suitable thickeners are polymeric thickeners, such as Aerosil® types (hydro- philic silicas), polysaccharides, more especially xanthan gum, guar-guar, agar-agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, also rela- tively high molecular weight polyethylene glycol monoesters and diesters of fatty acids, polyacrylates (for example Carbopols® [Goodrich] or Synthalens® [Sigma]), poly- acrylamides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as, for ex- ample, ethoxylated fatty acid glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylol propane, narrow-range fatty alcohol ethoxylates and elec- trolytes, such as sodium chloride and ammonium chloride.
Polymers
[0097] Suitable cationic polymers are, for example, cationic cellulose derivatives such as, for example, the quaternized hydroxyethyl cellulose obtainable from Amerchol un- der the name of Polymer JR 400®, cationic starch, copolymers of diallyl ammonium salts and acrylamides, quaternized vinyl pyrrolidone/vinyl imidazole polymers such as, for example, Luviquat® (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides such as, for example, Lauryldimonium Hydroxypro- pyl Hydrolyzed Collagen (Lamequat® L, Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as, for example, amodimethicone, copolymers of adipic acid and dimethylaminohydroxypropyl diethylenetriamine (Car- taretine®, Sandoz), copolymers of acrylic acid with dimethyl diallyl ammonium chloride (Merquat® 550, Chemviron), polyaminopolyamides and crosslinked water-soluble pol- ymers thereof, cationic chitin derivatives such as, for example, quaternized chitosan, optionally in microcrystalline distribution, condensation products of dihaloalkyls, for ex- ample dibromobutane, with bis-dialkylamines, for example bis-dimethylamino-1 ,3-pro- pane, cationic guar gum such as, for example, Jaguar®CBS, Jaguar®C-17, Jaguar®C- 16 of Celanese, quaternized ammonium salt polymers such as, for example, Mirapol® A-15, Mirapol® AD-1 , Mirapol® AZ-1 of Miranol and the various polyquaternium types (for example 6, 7, 32 or 37) which can be found in the market under the tradenames Rheocare® CC or Ultragel® 300.
[0098] Suitable anionic, zwitterionic, amphoteric and nonionic polymers are, for exam- ple, vinyl acetate/crotonic acid copolymers, vinyl pyrrolidone/vinyl acrylate copolymers, vinyl acetate/butyl maleate/isobornyl acrylate copolymers, methyl vinylether/maleic an- hydride copolymers and esters thereof, uncrosslinked and polyol-crosslinked poly- acrylic acids, acrylamidopropyl trimethylammonium chloride/acrylate copolymers, oc- tylacrylamide/methyl methacrylate/tert.-butylaminoethyl methacrylate/2-hydroxypropyl methacrylate copolymers, polyvinyl pyrrolidone, vinyl pyrrolidone/vinyl acetate copoly- mers, vinyl pyrrolidone/dimethylaminoethyl methacrylate/vinyl caprolactam terpoly- mers and optionally derivatized cellulose ethers and silicones. Pearlizing waxes
[0099] Suitable pearlizing waxes are, for example, alkylene glycol esters, especially ethylene glycol distearate; fatty acid alkanolamides, especially cocofatty acid diethan- olamide; partial glycerides, especially stearic acid monoglyceride; esters of polybasic, optionally hydroxysubstituted carboxylic acids with fatty alcohols containing 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; fatty compounds, such as for example fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty car- bonates which contain in all at least 24 carbon atoms, especially laurone and dis- tearylether; fatty acids, such as stearic acid, hydroxystearic acid or behenic acid, ring opening products of olefin epoxides containing 12 to 22 carbon atoms with fatty alco- hols containing 12 to 22 carbon atoms and/or polyols containing 2 to 15 carbon atoms and 2 to 10 hydroxyl groups and mixtures thereof.
Silicones
[00100] Suitable silicones can be chosen from the group consisting of: Acefylline Methylsilanol Mannuronate, Acetylmethionyl Methylsilanol Elastinate Acrylates/Be- henyl, Acrylate/Dimethicone Methacrylate Copolymer, Acrylates/Behenyl Methacry- late/Dimethicone Methacrylate Copolymer, Acrylates/Bis-Hydroxypropyl Dimethicone Crosspolymer, Acrylates/Dimethicone Copolymer, Acrylates/Dimethicone Methacry- late/Ethylhexyl Acrylate Copolymer, Acrylates/Dimethiconol Acrylate Copolymer, Acry- lates/Ethylhexyl Acrylate/Dimethicone Methacrylate Copolymer, Acrylates/Octylacryla- mide/Diphenyl Amodimethicone Copolymer, Acrylates/Polytrimethylsiloxymethacry- late Copolymer, Acrylates/Propyl Trimethicone Methacrylate Copolymer, Acry- lates/Stearyl Acrylate/Dimethicone Methacrylate Copolymer, Acrylates/Tridecyl Acry- late/Triethoxysilylpropyl Methacrylate/Dimethicone Methacrylate Copolymer, Acry- lates/Trifluoropropylmethacrylate/Polytrimethyl Siloxymethacrylate Copolymer, Amino Bispropyl Dimethicone, Aminoethylaminopropyl Dimethicone, Aminopropyl Dimethi- cone, Aminopropyl Phenyl Trimethicone, Aminopropyl Triethoxysilane, Ammonium Di- methicone PEG-7 Sulfate, Amodimethicone, Amodimethicone Hydroxystearate, Amodimethicone/Silsesquioxane Copolymer, Ascorbyl Carboxydecyl Trisiloxane, Ascorbyl Methylsilanol Pectinate, Behenoxy Dimethicone, Behentrimonium Dimethi- cone PEG-8 Phthalate, Behenyl Dimethicone, Bisamino PEG/PPG-41/3 Aminoethyl PG-Propyl Dimethicone, Bis-Aminopropyl/Ethoxy Aminopropyl Dimethicone, Bis(Bu- tylbenzoate) Diaminotriazine Aminopropyltrisiloxane, Bis-Butyldimethicone Polyglyc- eryl-3, Bis-Butyloxyamodimethicone/PEG-60 Copolymer, Bis(C13-15 Alkoxy) Hy- droxybutamidoamodimethicone, Bis(C13-15 Alkoxy) PG- Amodimethicone, Bis-(C1 -8 Alkyl Lauroyl Lysine Decylcarboxamide) Dimethicone, Bis-Cetyl Cetyl Dimethicone, Bis-Cetyl/PEG-8 Cetyl PEG-8 Dimethicone, Bis-Diphenylethyl Disiloxane, Bis-Ethyl Ethyl Methicone, Bis-Gluconamidoethylaminopropyl Dimethicone, Bis-Hydrogen Di- methicone, Bis- Hydroxyethoxypropyl Dimethicone Bis-Hydroxylauryl, Dimethi- cone/lPDI Copolymer, Bis- Hydroxy/Methoxy Amodimethicone, Bis-Hydroxypropyl Di- methicone Behenate, Bis-Hydroxypropyl Dimethicone/SMDI Copolymer, Bis-lsobutyl PEG-14/Amodimethicone Copolymer, Bis-lsobutyl PEG- 15/Amodimethicone Copoly- mer, Bis-lsobutyl PEG/PPG-20/35/Amodimethicone Copolymer, Bis- Isobutyl PEG/PPG-10/7/Dimethicone Copolymer, Bis-lsobutyl PEG-24/PPG-7/Dimethicone Copolymer, Bis-PEG-1 Dimethicone, Bis-PEG-4 Dimethicone, Bis-PEG-8 Dimethi- cone, Bis-PEG-12 Dimethicone, Bis-PEG-20 Dimethicone, Bis-PEG-12 Dimethicone Beeswax, Bis-PEG-12 Dimethicone Candelillate, Bis-PEG-15 Dimethicone/IPDI Co- polymer, Bis-PEG-15 Methyl Ether Dimethicone, Bis- PEG-18 Methyl Ether Dimethyl Silane, Bis-PEG/PPG-14/14 Dimethicone, Bis-PEG/PPG-15/5 Dimethicone, Bis- PEG/PPG-18/6 Dimethicone, Bis-PEG/PPG-20/20 Dimethicone, Bis-PEG/PPG- 16/16 PEG/PPG-16/16 Dimethicone, Bis-PEG/PPG-20/5 PEG/PPG-20/5 Dimethicone, Bi- sphenylhexamethicone, Bis-Phenylpropyl Dimethicone, Bispolyethylene Dimethicone, Bis- (Polyglyceryl-3 Oxyphenylpropyl) Dimethicone, Bis-(Polyglyceryl-7 Oxyphenylpro- pyl) Dimethicone, Bis-PPG-15 Dimethicone/IPDI Copolymer, Bis(PPG-7 Undeceneth- 21 ) Dimethicone, Bis-Stearyl Dimethicone, Bis-Trimethoxysilylethyl Tetramethyl- disiloxyethyl Dimethicone, Bis-Vinyldimethicone, Bis-Vinyl Dimethicone/Dimethicone Copolymer, Borage Seed Oil PEG-7 Dimethicone Esters, Butyl Acrylate/C6-14 Per- fluoroalkylethyl Acrylate/Mercaptopropyl Dimethicone Copolymer, Butyl Acrylate/Hy- droxypropyl Dimethicone Acrylate Copolymer, Butyl Dimethicone Acrylate/Cyclohexyl- methacrylate/Ethylhexyl Acrylate Copolymer, Butyldimethicone Methacrylate/Methyl Methacrylate Crosspolymer, t-Butyl Dimethyl Silyl Grape Seed Extract, Butyl Polydi- methylsiloxyl Ethylene/Propylene/Vinylnorbornene Copolymer, C6-8 Alkyl C3-6 Alkyl Glucoside Dimethicone, C20-24 Alkyl Dimethicone, C24-28 Alkyl Dimethicone, C26-28 Alkyl Dimethicone, C30-45 Alkyl Dimethicone, C30-60 Alkyl Dimethicone, C32 Alkyl Dimethicone, C30-45 Alkyl Dimethicone/Polycyclohexene Oxide Crosspolymer, C26- 28 Alkyldimethylsilyl Polypropylsilsesquioxane, C30-45 Alkyldimethylsilyl Polypro- pylsilsesquioxane, C20-24 Alkyl Methicone, C24-28 Alkyl Methicone, C26-28 Alkyl Me- thicone, C30-45 Alkyl Methicone, C20-28 Alkyl Perfluorodecylethoxy Dimethicone, C26-54 Alkyl Tetradecyl Dimethicone, Capryl Dimethicone, Caprylyl Dimethicone Eth- oxy Glucoside, Caprylyl Methicone, Caprylyl Trimethicone, Carboxydecyl Trisiloxane, Castor Oil Bis-Hydroxypropyl Dimethicone Esters Cerotyl Dimethicone, Cetearyl Di- methicone Crosspolymer, Cetearyl Dimethicone/Vinyl Dimethicone Crosspolymer, Ce- tearyl Methicone, Cetrimonium Carboxydecyl PEG-8 Dimethicone, Cetrimonium Dime- thicone PEG-7 Phthalate, Cetyl Behenyl Dimethicone, Cetyl Dimethicone, Cetyl Dime- thicone/Bis-Vinyldimethicone Crosspolymer, Cetyl Hexacosyl Dimethicone, Cetyloxy Dimethicone, Cetyl PEG-8 Dimethicone, Cetyl PEG/PPG-15/15 Butyl Ether Dimethi- cone, Cetyl PEG/PPG-7/3 Dimethicone, Cetyl PEG/PPG-10/1 Dimethicone, Cetyl Tri- ethylmonium Dimethicone PEG-8 Phthalate, Cetyl Triethylmonium Dimethicone PEG- 8 Succinate, Copper Acetyl Tyrosinate Methylsilanol, Copper PCA Methylsilanol, C4- 14 Perfluoroalkylethoxy Dimethicone, Cycloethoxymethicone, Cycloheptasiloxane, Cyclohexasiloxane, Cyclomethicone, Cyclopentasiloxane, Cyclophenylmethicone, Cy- clotetrasiloxane, mCyclovinylmethicone, Cystine Bis-PG-Propyl Silanetriol, DEA PG- Propyl PEG/PPG-18/21 Dimethicone, Diisostearoyl Trimethylolpropane Siloxy Silicate, Dilauroyl Trimethylolpropane Siloxy Silicate, Dilinoleamidopropyl Dimethylamine Di- methicone PEG-7 Phosphate, Dimethicone, Dimethicone Crosspolymer, Dimethicone Crosspolymer-3, Dimethicone/Divinyldimethicone/Silsesquioxane Crosspolymer, Di- methicone Ethoxy Glucoside, Dimethicone Hydroxypropyl Trimonium Chloride, Dime- thicone/Mercaptopropyl Methicone Copolymer, Dimethicone PEG-15 Acetate Dimethi- cone PEG-8 Adipate, Dimethicone PEG-7 Avocadoate, Dimethicone PEG-8 Avoca- doate, Dimethicone PEG-8 Beeswax, Dimethicone PEG-8 Benzoate, Dimethicone PEG-8 Borageate, Dimethicone PEG-7 Cocoate, Dimethicone/PEG-10 Crosspolymer, Dimethicone/PEG-10/15 Crosspolymer, Dimethicone/PEG-15 Crosspolymer, Dimethi- cone PEG-7 Isostearate, Dimethicone PEG-8 Isostearate, Dimethicone PEG-7 Lac- tate, Dimethicone PEG-8 Lanolate, Dimethicone PEG-8 Laurate, Dimethicone PEG-8 Meadowfoamate, Dimethicone PEG-7 Octyldodecyl Citrate, Dimethicone PEG-7 Oli- vate, Dimethicone PEG-8 Olivate, Dimethicone PEG-7 Phosphate, Dimethicone PEG- 8 Phosphate, Dimethicone PEG-10 Phosphate, Dimethicone PEG-7 Phthalate, Dime- thicone PEG-8 Phthalate, Dimethicone PEG-8 Polyacrylate, Dimethicone PEG/PPG- 20/23 Benzoate, Dimethicone PEG/PPG-7/4 Phosphate, Dimethicone PEG/PPG-12/4 Phosphate, Dimethicone PEG-7 Succinate, Dimethicone PEG-8 Succinate, Dimethi- cone PEG-7 Sulfate, Dimethicone PEG-7 Undecylenate, Dimethicone PG-Diethyl- monium Chloride, Dimethicone/Phenyl Vinyl Dimethicone Crosspolymer, Dimethi- cone/Polyglycerin-3 Crosspolymer, Dimethicone/PPG-20 Crosspolymer, Dimethicone Propylethylenediamine Behenate, Dimethicone Propyl PG-Betaine, Dimethi- cone/Silsesquioxane Copolymer, Dimethicone Silylate, Dimethicone?/inyl Dimethi- cone Crosspolymer, Dimethicone/Vinyltrimethylsiloxysilicate Crosspolymer, Dimethi- conol, Dimethiconol Arginine, Dimethiconol Beeswax, Dimethiconol Behenate, Dime- thiconol Borageate, Dimethiconol Candelillate, Dimethiconol Carnaubate, Dimethi- conol Cysteine, Dimethiconol Dhupa Butterate, Dimethiconol Fluoroalcohol Dilinoleic Acid, Dimethiconol Hydroxystearate, Dimethiconol lllipe Butterate, Dimethiconol/IPDI Copolymer, Dimethiconol Isostearate, Dimethiconol Kokum Butterate, Dimethiconol Lactate, Dimethiconol Meadowfoamate, Dimethiconol Methionine, Dimethiconol/Me- thylsilanol/Silicate Crosspolymer, Dimethiconol Mohwa Butterate, Dimethiconol Pan- thenol, Dimethiconol Sal Butterate, Dimethiconol/Silica Crosspolymer, Dimethi- conol/Silsesquioxane Copolymer, Dimethiconol Stearate, Dimethiconol/Stearyl, Methi- cone/Phenyl Trimethicone Copolymer, Dimethoxysilyl Ethylenediaminopropyl Dimethi- cone, Dimethylaminopropylamido PCA Dimethicone, Dimethyl Oxobenzo Dioxasilane, Dimethylsilanol Hyaluronate, Dioleyl Tocopheryl Methylsilanol, Diphenyl Amodimethi- cone, Diphenyl Dimethicone, Diphenyl Dimethicone Crosspolymer Diphenyl Dimethi- cone?/inyl Diphenyl Dimethicone/Silsesquioxane Crosspolymer, Diphenylethyl Ben- zyloxy Dilsiloxane, Diphenylisopropyl Dimethicone, Diphenylsiloxy Phenyl/Propyl Tri- methicone, Diphenylsiloxy Phenyl Trimethicone Disiloxane, Disodium Amodimethi- cone Disuccinamide, Disodium PEG-12 Dimethicone Sulfosuccinate, Disodium PEG- 8 Lauryl Dimethicone Sulfosuccinate, Divinyldimethicone/Dimethicone Copolymer, Divinyldimethicone/Dimethicone Crosspolymer, Drometrizole Trisiloxane, Ethylhexyl Acrylate/VP/Dimethicone Methacrylate Copolymer, Ethyl Methicone, Ethyl Trisiloxane, Fluoro C2-8 Alkyldimethicone, Gluconamidopropyl Aminopropyl Dimethicone, 4-(2- Beta-Glucopyranosiloxy) Propoxy-2-Hydroxybenzophenone, Glyceryl Undecyl Dime- thicone, Glycidoxy Dimethicone, Hexadecyl Methicone, Hexyl Dimethicone, Hexyl Methicone, Hexyltrimethoxysilane, Hydrogen Dimethicone, Hydrogen Dimethi- cone/Octyl Silsesquioxane Copolymer, Hydrolyzed Collagen PG-Propyl Dimethiconol, Hydrolyzed Collagen PG-Propyl Methylsilanediol, Hydrolyzed Collagen PG-Propyl Silanetriol, Hydrolyzed Keratin PG-Propyl Methylsilanediol, Hydrolyzed Sesame Pro- tein PG-Propyl Methylsilanediol, Hydrolyzed Silk PG-Propyl Methylsilanediol, Hydro- lyzed Silk PG-Propyl Methylsilanediol Crosspolymer, Hydrolyzed Soy Protein/Dimethi- cone PEG-7 Acetate, Hydrolyzed Soy Protein PG-Propyl Methylsilanediol, Hydrolyzed Vegetable Protein PG-Propyl Silanetriol, Hydrolyzed Wheat Protein/Cystine Bis-PG- Propyl Silanetriol Copolymer, Hydrolyzed Wheat Protein/Dimethicone PEG-7 Acetate, Hydrolyzed Wheat Protein/Dimethicone PEG-7 Phosphate Copolymer, Hydrolyzed Wheat Protein PG-Propyl Methylsilanediol, Hydrolyzed Wheat Protein PG-Propyl Silanetriol, Hydroxyethyl Acetomonium PG-Dimethicone, Hydroxypropyldimethicone, Hydroxypropyl Dimethicone Behenate, Hydroxypropyl Dimethicone Isostearate, Hy- droxypropyl Dimethicone Stearate, Isobutylmethacrylate/Bis-Hydroxypropyl Dimethi- cone Acrylate Copolymer, Isobutylmethacrylate/Trifluoroethylmethacrylate/Bis-Hy- droxypropyl Dimethicone Acrylate Copolymer, Isopentyl Trimethoxycinnamate Trisilox- ane, lsopolyglyceryl-3 Dimethicone, lsopolyglyceryl-3 Dimethiconol, Isopropyl Titanium Triisostearate/Triethoxysilylethyl, Polydimethylsiloxyethyl Dimethicone Crosspolymer, Isostearyl Carboxydecyl PEG-8 Dimethicone, Lactoyl Methylsilanol Elastinate, Lauryl Dimethicone, Lauryl Dimethicone PEG-15 Crosspolymer, Lauryl Dimethicone PEG- 10 Phosphate, Lauryl Dimethicone/Polyglycerin-3 Crosspolymer, Lauryl Methicone, Lau- ryl PEG-8 Dimethicone, Lauryl PEG-10 Methyl Ether Dimethicone, Lauryl PEG-9 Pol- ydimethylsiloxyethyl Dimethicone, Lauryl PEG/PPG-18/18 Methicone, Lauryl Phenyli- sopropyl Methicone, Lauryl Phenylpropyl Methicone, Lauryl Polydimethylsiloxyethyl Dimethicone/Bis-Vinyldimethicone Crosspolymer, Lauryl Polyglyceryl-3 Polydime- thylsiloxyethyl Dimethicone, Lauryl Trimethicone, Linoleamidopropyl PG-Dimonium Chloride Phosphate Dimethicone, Methacryloyl Propyltrimethoxysilane, Methicone, Methoxy Amodimethicone/Silsesquioxane Copolymer, Methoxycinnamidopropyl Pol- ysilsesquioxane, Methoxycinnamoylpropyl Silsesquioxane Silicate, Methoxy PEG-13 Ethyl Polysilsesquioxane, Methoxy PEG/PPG-7/3 Aminopropyl Dimethicone, Methoxy PEG/PPG-25/4 Dimethicone, Methoxy PEG-10 Propyltrimethoxysilane, Methyleugenyl PEG- 8 Dimethicone, Methylpolysiloxane Emulsion, Methylsilanol Acetylmethionate, Methylsilanol Acetyltyrosine, Methylsilanol Ascorbate, Methylsilanol Carboxymethyl Theophylline, Methylsilanol Carboxymethyl Theophylline Alginate, Methylsilanol Elas- tinate, Methylsilanol Glycyrrhizinate, Methylsilanol Hydroxyproline, Methylsilanol Hy- droxyproline Aspartate, Methylsilanol Mannuronate, Methylsilanol PCA, Methylsilanol PEG-7 Glyceryl Cocoate, Methylsilanol/Silicate Crosspolymer, Methylsilanol Spiruli- nate, Methylsilanol Tri-PEG-8 Glyceryl Cocoate, Methyl Trimethicone, Methyltri- methoxysilane, Myristylamidopropyl Dimethylamine Dimethicone PEG-7 Phosphate, Myristyl Methicone, Myristyl Trisiloxane, Nylon-61 1 /Dimethicone Copolymer, PCA Di- methicone, PEG-7 Amodimethicone, PEG-8 Amodimethicone, PEG-8 Cetyl Dimethi- cone, PEG-3 Dimethicone, PEG-6 Dimethicone, PEG-7 Dimethicone, PEG-8 Dimethi- cone, PEG-9 Dimethicone, PEG-10 Dimethicone, PEG-12 Dimethicone, PEG-14 Di- methicone, PEG-17 Dimethicone, PEG-10 Dimethicone Crosspolymer, PEG-12 Dimethicone Crosspolymer, PEG-8 Dimethicone Dimer Dilinoleate, PEG-8 Dimethi- cone/Dimer Dilinoleic Acid Copolymer, PEG-10 Dimethicone/Vinyl Dimethicone Cross- polymer, PEG-8 Distearmonium Chloride PG-Dimethicone, PEG-10/Lauryl Dimethi- cone Crosspolymer, PEG- 15/Lauryl Dimethicone Crosspolymer, PEG-15/Lauryl Poly- dimethylsiloxyethyl Dimethicone Crosspolymer, PEG-8 Methicone, PEG-6 Methicone Acetate, PEG-6 Methyl Ether Dimethicone, PEG- 7 Methyl Ether Dimethicone, PEG-8 Methyl Ether Dimethicone, PEG-9 Methyl Ether Dimethicone, PEG-10 Methyl Ether Dimethicone, PEG-1 1 Methyl Ether Dimethicone, PEG-32 Methyl Ether Dimethicone, PEG-8 Methyl Ether Triethoxysilane, PEG-10 Nonafluorohexyl Dimethicone Copoly- mer, PEG-4 PEG-12 Dimethicone, PEG-8 PG-Coco-Glucoside Dimethicone, PEG-9 Polydimethylsiloxyethyl Dimethicone, PEG/PPG-20/22 Butyl Ether Dimethicone, PEG/PPG-22/22 Butyl Ether Dimethicone, PEG/PPG-23/23 Butyl Ether Dimethicone, PEG/PPG-24/18 Butyl Ether Dimethicone, PEG/PPG-27/9 Butyl Ether Dimethicone, PEG/PPG-3/10 Dimethicone, PEG/PPG-4/12 Dimethicone, PEG/PPG-6/4 Dimethi- cone, PEG/PPG-6/1 1 Dimethicone, PEG/PPG-8/14 Dimethicone, PEG/PPG-8/26 Di- methicone, PEG/PPG-10/2 Dimethicone, PEG/PPG-12/16 Dimethicone, PEG/PPG- 12/18 Dimethicone, PEG/PPG-14/4 Dimethicone, PEG/PPG-15/5 Dimethicone, PEG/PPG-15/15 Dimethicone, PEG/PPG-16/2 Dimethicone, PEG/PPG-16/8 Dimethi- cone, PEG/PPG-17/18 Dimethicone, PEG/PPG-18/6 Dimethicone, PEG/PPG-18/12 Dimethicone, PEG/PPG-18/18 Dimethicone, PEG/PPG-19/19 Dimethicone, PEG/PPG-20/6 Dimethicone, PEG/PPG-20/15 Dimethicone, PEG/PPG-20/20 Dime- thicone, PEG/PPG-20/23 Dimethicone, PEG/PPG-20/29 Dimethicone, PEG/PPG- 22/23 Dimethicone, PEG/PPG-22/24 Dimethicone, PEG/PPG-23/6 Dimethicone, PEG/PPG-25/25 Dimethicone, PEG/PPG-27/27 Dimethicone, PEG/PPG-30/10 Dime- thicone, PEG/PPG-25/25 Dimethicone/Acrylates Copolymer, PEG/PPG-20/22 Methyl Ether Dimethicone, PEG/PPG-24/24 Methyl Ether Glycidoxy Dimethicone, PEG/PPG- 10/3 Oleyl Ether Dimethicone, PEG/PPG-5/3 Trisiloxane, PEG-4 Trifluoropropyl Dime- thicone Copolymer, PEG-8 Trifluoropropyl Dimethicone Copolymer, PEG-10 Trifluoro- propyl Dimethicone Copolymer, PEG-8 Trisiloxane, Perfluorocaprylyl riethoxysilylethyl Methicone, Perfluorononyl Dimethicone, Perfluorononyl Dimethicone/Methi- cone/Amodimethicone Crosspolymer, Perfluorononylethyl Carboxydecyl Behenyl Di- methicone, Perfluorononylethyl Carboxydecyl Hexacosyl Dimethicone, Perfluorono- nylethyl Carboxydecyl Lauryl/Behenyl Dimethicone, Perfluorononylethyl Carboxydecyl Lauryl Dimethicone, Perfluorononylethyl Carboxydecyl PEG-8 Dimethicone, Perfluoro- nonylethyl Carboxydecyl PEG-10 Dimethicone, Perfluorononylethyl Dimethicone/Me- thicone Copolymer, Perfluorononylethyl PEG-8 Dimethicone, Perfluorononylethyl Stearyl Dimethicone, Perfluorooctylethyl/Diphenyl Dimethicone Copolymer, Perfluo- rooctylethyl Triethoxysilane, Perfluorooctylethyl Trimethoxysilane, Perfluorooctylethyl Trisiloxane, Perfluorooctyl Triethoxysilane, PG-Amodimethicone, Phenethyl Dimethi- cone, Phenethyl Disiloxane, Phenyl Dimethicone, Phenylisopropyl Dimethicone, Phe- nyl Methicone, Phenyl Methiconol, Phenylpropyldimethylsiloxysilicate, Phenylpropyl Ethyl Methicone, Phenyl Propyl Trimethicone, Phenyl Propyl Trimethicone/Diphenyl- methicone, Phenyl Trimethicone, Platinum Divinyldisiloxane, Polyacrylate-6, Polydi- ethylsiloxane, Polydimethylsiloxyethyl Dimethicone/Bis-Vinyldimethicone Crosspolymer, Polydimethylsiloxyethyl Dimethicone/Methicone Copolymer, Polydime- thylsiloxy PEG/PPG-24/19 Butyl Ether Silsesquioxane, Polydimethylsiloxy PPG- 13 Butyl Ether Silsesquioxane, Polyglyceryl-3 Disiloxane Dimethicone, Polyglyceryl- 3/Lauryl Polydimethylsiloxyethyl Dimethicone Crosspolymer, Polyglyceryl-3 Polydime- thylsiloxyethyl Dimethicone, Poly(Glycol Adipate)/Bis-Hydroxyethoxypropyl Dimethi- cone Copolymer, Polymethylsilsesquioxane, Polymethylsilsesquioxane/Trime- thylsi loxysilicate, Polyphenylsilsesquioxane, Polypropylsilsesquioxane, Polysilicone-1 , Polysilicone-2, Polysilicone-3, Polysilicone-4, Polysilicone-5, Polysilicone-6, Polysili- cone-7, Polysilicone-8, Polysilicone-9, Polysilicone-10, Polysilicone-1 1 , Polysilicone- 12, Polysilicone-13, Polysilicone-14, Polysilicone-15, Polysilicone-16, Polysilicone-17, Polysilicone-18, Polysilicone-19, Polysilicone-20, Polysilicone-21 , Polysilicone-18 Ce- tyl Phosphate, Polysilicone-1 Crosspolymer, Polysilicone-18 Stearate, Polyurethane- 10, Potassium Dimethicone PEG-7 Panthenyl Phosphate, Potassium Dimethicone PEG- 7 Phosphate, PPG-12 Butyl Ether Dimethicone, PPG-2 Dimethicone, PPG-12 Dimethicone, PPG-27 Dimethicone, PPG-4 Oleth-10 Dimethicone, Propoxytetramethyl Piperidinyl Dimethicone, Propyl Trimethicone, Quaternium-80, Retinoxytrime- thylsilane, Silanediol Salicylate, Silanetriol, Silanetriol Arginate, Silanetriol Glutamate, Silanetriol Lysinate, Silanetriol Melaninate, Silanetriol Trehalose Ether, Silica, Silica Dimethicone Silylate, Silica Dimethyl Silylate, Silica Silylate, Silicon Carbide, Sili- cone Quaternium-1 , Silicone Quaternium-2, Silicone Quaternium-2 Panthenol Succin- ate, Silicone Quaternium-3, Silicone Quaternium-4, Silicone Quaternium-5, Silicone Quaternium-6, Silicone Quaternium-7, Silicone Quaternium-8, Silicone Quaternium-9, Silicone Quaternium-10, Silicone Quaternium-1 1 , Silicone Quaternium-12, Silicone Quaternium-15, SiliconeQuaternium-16, Silicone Quaternium-16/Glycidoxy Dimethi- cone Crosspolymer, Silicone Quaternium-17, Silicone Quaternium- 18, Silicone Qua- ternium-19, Silicone Quaternium-20, Silicone Quaternium-21 , Silicone Quaternium- 22, Silicone Quaternium-24, Silicone Quaternium-25, Siloxanetriol Alginate, Silox- anetriol Phytate, Simethicone, Sodium Carboxydecyl PEG-8 Dimethicone, Sodium Di- methicone PEG-7 Acetyl Methyltaurate, Sodium Hyaluronate Dimethylsilanol, Sodium Lactate Methylsilanol, Sodium Mannuronate Methylsilanol, Sodium PCA Methylsilanol, Sodium PG-Propyldimethicone Thiosulfate Copolymer, Sodium PG-Propyl Thiosulfate Dimethicone, Sodium Propoxyhydroxypropyl Thiosulfate Silica, Sorbityl Silanediol, Soy Triethoxysilylpropyldimonium Chloride, Stearalkonium Dimethicone PEG-8 Phthalate, Stearamidopropyl Dimethicone, Steardimonium Hydroxypropyl Panthenyl PEG-7 Dimethicone Phosphate Chloride, Steardimonium Hydroxypropyl PEG-7 Dime- thicone Phosphate Chloride, Stearoxy Dimethicone, Stearoxymethicone/Dimethicone Copolymer, Stearoxytrimethylsilane, Stearyl Aminopropyl Methicone, Stearyl Dimethi- cone, Stearyl/Lauryl Methacrylate Crosspolymer, Stearyl Methicone, Stearyl Triethox- ysilanek, Stearyl Trimethicone, Styrene/Acrylates/Dimethicone Acrylate Crosspoly- mer, Styrene/Acrylates/Dimethicone Copolymer, TEA-Dimethicone PEG-7 Phosphate, Tetrabutoxypropyl Trisiloxane, Tetramethyl Hexaphenyl Tetrasiloxane, Tetramethyl Tetraphenyl Trisiloxane, Tocopheryloxypropyl Trisiloxane, Trideceth-9 PG-Amodime- thicone, Triethoxycaprylylsilane, Triethoxysilylethyl Dimethicone/Methicone Copoly- mer, Triethoxysilylethyl Polydimethylsiloxyethyl Dimethicone, Triethoxysilylethyl Polydimethylsiloxyethyl Hexyl Dimethicone, Triethoxysilylpropylcarbamoyl Ethoxypro- pyl Butyl Dimethicone, Trifluoromethyl C1 -4 Alkyl Dimethicone, Trifluoropropyl Cyclo- pentasiloxane, Trifluoropropyl Cyclotetrasiloxane, Trifluoropropyl Dimethicone, Tri- fluoropropyl Dimethicone/PEG-10 Crosspolymer, Trifluoropropyl Dimethicone/Tri- fluoropropyl Divinyldimethicone Crosspolymer, Trifluoropropyl Dimethicone/Vinyl Tri- fluoropropyl, Dimethicone/Silsesquioxane Crosspolymer, Trifluoropropyl Dimethiconol, Trifluoropropyldimethyl/trimethylsiloxysilicate, Trifluoropropyl Methicone, Trimethox- ycaprylylsilane, Trimethoxysilyl Dimethicone, Trimethyl Pentaphenyl Trisiloxane, Tri- methylsiloxyamodimethicone, Trimethylsiloxyphenyl Dimethicone, Trimethylsiloxysili- cate, Trimethylsiloxysilicate/Dimethicone Crosspolymer, Trimethylsiloxysilicate/Dime- thiconol Crosspolymer, Trimethylsiloxysilylcarbamoyl Pullulan, Trimethylsilyl Hydro- lyzed Conchiolin Protein PG-Propyl Methylsilanediol Crosspolymer, Trimethylsilyl Hy- drolyzed Silk PG-Propyl Methylsilanediol Crosspolymer, Trimethylsilyl Hydrolyzed Wheat Protein PG-Propyl Methylsilanediol Crosspolymer, Trimethylsilyl Pullulan, Tri- methylsilyl Trimethylsiloxy Glycolate, Trimethylsilyl Trimethylsiloxy Lactate, Trime- thylsilyl Trimethylsiloxy Salicylate, Triphenyl Trimethicone, Trisiloxane, Tris-Tribu- toxysiloxymethylsilane, Undecylcrylene Dimethicone, Vinyl Dimethicone, Vinyl Dime- thicone/Lauryl Dimethicone Crosspolymer, Vinyl Dimethicone/Methicone Silsesquiox- ane Crosspolymer, Vinyldimethyl/Trimethylsiloxysilicate Stearyl Dimethicone Cross- polymer, VP/Dimethiconylacrylate/Polycarbamyl/Polyglycol Ester, Zinc Carboxydecyl Trisiloxane and Zinc Dimethicone PEG-8 Succinate and mixtures thereof.
[00101] More preferably the silicones to be contained in the mixture according to the inventions are Dimethicone, Cyclomethicone, Phenyl Trimethicone, Cyclohexasilox- ane and Cyclopentasiloxane. A detailed overview of suitable volatile silicones can be found in Todd et al. in Cosm. Toil. 91 , 27 (1976).
Waxes and stabilizers
[00102] Besides natural oils used, waxes may also be present in the preparations, more especially natural waxes such as, for example, candelilla wax, carnauba wax, Japan wax, espartograss wax, cork wax, guaruma wax, rice oil wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, spermaceti, lanolin (wool wax), uro- pygial fat, ceresine, ozocerite (earth wax), petrolatum, paraffin waxes and microwaxes; chemically modified waxes (hard waxes) such as, for example, montan ester waxes, sasol waxes, hydrogenated jojoba waxes and synthetic waxes such as, for example, polyalkylene waxes and polyethylene glycol waxes.
[00103] Metal salts of fatty acids such as, for example, magnesium, aluminium and/or zinc stearate or ricinoleate may be used as stabilizers. Primary sun protection filters
[00104] Primary sun protection filters in the context of the invention are, for example, organic substances (light filters) which are liquid or crystalline at room temperature and which are capable of absorbing ultraviolet radiation and of releasing the energy ab- sorbed in the form of longer-wave radiation, for example heat.
[00105] The formulations according to the invention advantageously contain at least one UV-A filter and/or at least one UV-B filter and/or a broadband filter and/or at least one inorganic pigment. Formulations according to the invention preferably contain at least one UV-B filter or a broadband filter, more particularly preferably at least one UV- A filter and at least one UV-B filter.
[00106] The UV filters cited below which can be used within the context of the present invention are preferred but naturally are not limiting. UV filters which are preferably used are selected from the group consisting of one, two, three, four, five or more of the following species:
Figure imgf000077_0001
Figure imgf000078_0001
[00107] In a preferred embodiment the sun protection filter forming component (ii) rep- resents a blend of UV-A- and UV-B-filters selected from the group consisting of ho- mosalate, octocrylene, bis-ethylhexyloxyphenol methoxyphenyl triazine, butyl methox- ydibenzoylmethane, ethylhexyl salicylate and mixtures thereof. Particular preferred is a blend of all these filters which is commercially available in the market under the trademark NeoHeliopan® Flat (SYMRISE), which also subject to WO 2020 088778 A1 .
[00108] Suitable pigments encompass oxides of titanium (TiO2), zinc (ZnO), iron (Fe2O3), zirconium (ZrO2), silicon (SiO2), manganese (e.g. MnO), aluminium (AI2O3), cerium (e.g. Ce2O3) and/or mixtures thereof.
[00109] In a further preferred embodiment a formulation according to the invention con- tains a total amount of sunscreen agents, i.e. in particular UV filters and/or inorganic pigments (UV filtering pigments) so that the formulation according to the invention has a light protection factor of greater than or equal to 5 and up to 50. Such formulations according to the invention are particularly suitable for protecting the skin and hair.
Secondary sun protection filters
[00110] Besides the groups of primary sun protection factors mentioned above, sec- ondary sun protection factors of the antioxidant type may also be used. Secondary sun protection factors of the antioxidant type interrupt the photochemical reaction chain which is initiated when UV rays penetrate into the skin. Typical examples are amino acids (for example glycine, histidine, tyrosine, tryptophane) and derivatives thereof, imidazoles (for example urocanic acid) and derivatives thereof, peptides, such as D,L- carnosine, D-carnosine, L-carnosine and derivatives thereof (for example anserine), carotinoids, carotenes (for example alpha-carotene, beta-carotene, lycopene) and de- rivatives thereof, chlorogenic acid and derivatives thereof, liponic acid and derivatives thereof (for example dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (for example thioredoxine, glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, alpha-linoleyl, cholesteryl and glyceryl esters thereof) and their salts, dilaurylthiodipropionate, dis- tearylthiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, pep- tides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (for ex- ample butionine sulfoximines, homocysteine sulfoximine, butionine sulfones, penta-, hexa- and hepta-thionine sulfoximine) in very small compatible dosages, also (metal) chelators (for example alpha-hydroxyfatty acids, palmitic acid, phytic acid, lactoferrine), alpha-hydroxy acids (for example citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and derivatives thereof, unsatu- rated fatty acids and derivatives thereof (for example linoleic acid, oleic acid), folic acid and derivatives thereof, ubiquinone and ubiquinol and derivatives thereof, vitamin C and derivatives thereof (for example ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (for example vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and coniferyl benzoate of benzoin resin, rutinic acid and derivatives thereof, glycosyl rutin, ferulic acid, furfurylidene glucitol, carno- sine, butyl hydroxytoluene, butyl hydroxyanisole, nordihydroguaiac resin acid, nordihy- droguaiaretic acid, trihydroxybutyrophenone, uric acid and derivatives thereof, man- nose and derivatives thereof, superoxide dismutase, titanium dioxide (for example dis- persions in ethanol), zinc and derivatives thereof (for example ZnO, ZnSO4), selenium and derivatives thereof (for example selenium methionine), stilbenes and derivatives thereof (for example stilbene oxide, trans-stilbene oxide) and derivatives of these ac- tive substances suitable for the purposes of the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids).
[00111] Advantageous inorganic secondary light protection pigments are finely dis- persed metal oxides and metal salts which are also mentioned in WO 2005 123101 A1 . The total quantity of inorganic pigments, in particular hydrophobic inorganic micro- pigments in the finished cosmetic preparation according to the present invention is advantageously from 0.1 to 30% by weight, preferably 0.5 to 10.0% by weight, in each case based on the total weight of the preparation.
[00112] Also preferred are particulate UV filters or inorganic pigments, which can op- tionally be hydrophobed, can be used, such as the oxides of titanium (TiO2), zinc (ZnO), iron (Fe2O3), zirconium (ZrO2), silicon (SiO2), manganese (e.g. MnO), alumin- ium (AI2O3), cerium (e.g. Ce2O3) and/or mixtures thereof.
Biogenic agents and antioxidants
[00113] Biogenic active substances include, for example, tocopherol, tocopherol ace- tate, tocopherol palmitate, ascorbic acid, (deoxy)ribonucleic acid and its fragmentation products, β -glucans, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts, such as such as prunus extract, bambaranus extract and vitamin complexes.
[00114] Antioxidants interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin. Typical examples are amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides like D,L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. -carotene, lycopene) and their derivates, chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g. dihy- drolic acid), aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin, gluta- thione, cysteine, cystine, cystamin and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, linoleyl, cholesteryl and glyceryl esters) and their salts Dilaurylthiodipropionate, ditearylthiodipropionate, thiodipropionic acid and its de- rivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g. (e.g. buthionine sulfoximines, homocysteine sul- foximines, butionine sulfones, penta-, hexa-, heptathionine sulfoximines) in very low tolerated dosages (e.g. pmol to mol/kg), furthermore (metal) chelators (e.g. hydroxy fatty acids, palmitic acid, phytinic acid, lactoferrin), hydroxy acids (e.g. citric acid, lactic acid, malic acid), humic acid, gallic acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g. linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and its derivatives (e.g. ascorbyl palmitate, Mg-ascorbyl phosphate, ascorbylacetate), tocopherols and derivatives (e.g. vitamin E acetate), vit- amin A and derivates (vitamin A palmitate) as well as conifer aryl benzoate of benzoic resin, rutinic acid and its derivatives, glycosylrutin, ferulic acid, furfurylidene glucitol, carnosine, butyl hydroxytoluene, butylhydroxyanisole, nordihydroguaiac resin acid, nordihydroguajaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, man- nose and its derivatives, superoxide dismutase, zinc and its derivatives (e.g. ZnO, ZnSO4) selenium and its derivatives (e.g. selenium-methionine), stilbenes and their derivatives (e.g. styrene oxide, trans-stilbene oxide) and the derivatives suitable for the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these named active substances.
Actives modulating hair pigmentation
[00115] Preferred active ingredients for hair lightening are selected from the group con- sisting of: kojic acid (5-hydroxy-2-hydroxymethyl-4-pyranone), kojic acid derivatives, preferably kojic acid dipalmitate, arbutin, ascorbic acid, ascorbic acid derivatives, pref- erably magnesium ascorbyl phosphate, hydroquinone, hydroquinone derivatives, res- orcinol, resorcinol derivatives, preferably 4-alkylresorcinols and 4-(1 -phenylethyl)1 ,3- dihydroxybenzene (phenylethyl resorcinol), cyclohexylcarbamates (preferably one or more cyclohexyl carbamates disclosed in WO 2010/122178 and WO 2010/097480), sulfur-containing molecules, preferably glutathione or cysteine, alpha-hydroxy acids (preferably citric acid, lactic acid, malic acid), salts and esters thereof, N-acetyl tyrosine and derivatives, undecenoyl phenylalanine, gluconic acid, chromone derivatives, pref- erably aloesin, flavonoids, 1 -aminoethyl phosphinic acid, thiourea derivatives, ellagic acid, nicotinamide (niacinamide), zinc salts, preferably zinc chloride or zinc gluconate, thujaplicin and derivatives, triterpenes, preferably maslinic acid, sterols, preferably er- gosterol, benzofuranones, preferably senkyunolide, vinyl guiacol, ethyl guiacol, dionic acids, preferably octodecene dionic acid and/or azelaic acid, inhibitors of nitrogen ox- ide synthesis, preferably L-nitroarginine and derivatives thereof, 2,7-dinitroindazole or thiocitrulline, metal chelators (preferably alpha-hydroxy fatty acids, phytic acid, humic acid, bile acid, bile extracts, EDTA, EGTA and derivatives thereof), retinoids, soy milk and extract, serine protease inhibitors or lipoic acid or other synthetic or natural active ingredients for skin and hair lightening, the latter preferably used in the form of an extract from plants, preferably bearberry extract, rice extract, papaya extract, turmeric extract, mulberry extract, bengkoang extract, nutgrass extract, liquorice root extract or constituents concentrated or isolated therefrom, preferably glabridin or licochalcone A, artocarpus extract, extract of rumex and ramulus species, extracts of pine species (pi- nus), extracts of vitis species or stilbene derivatives isolated or concentrated therefrom, saxifrage extract, scutelleria extract, grape extract and/or microalgae extract, in partic- ular Tetraselmis suecica Extract.
[00116] Advantageous skin and hair tanning active ingredients in this respect are sub- strates or substrate analogues of tyrosinase such as L-tyrosine, N-acetyl tyrosine, L- DOPA or L-dihydroxyphenylalanine, xanthine alkaloids such as caffeine, theobromine and theophyl-line and derivatives thereof, proopiomelanocortin peptides such as ACTH, alpha-MSH, peptide analogues thereof and other substances which bind to the melanocortin receptor, peptides such as Val-Gly-Val-Ala-Pro-Gly, Lys-lle- Gly-Arg-Lys or Leu-lle-Gly-Lys, purines, pyrimidines, folic acid, copper salts such as copper glu- conate, chloride or pyrrolidonate, 1 ,3,4-oxadiazole-2-thiols such as 5-pyrazin-2-yl- 1 ,3,4-oxadiazole-2-thiol, curcumin, zinc diglycinate (Zn(Gly)2), manganese(ll) bicar- bonate complexes ("pseudocat-alases") as described for example in EP 0 584 178, tetrasubstituted cyclohexene deriva-tives as described for example in WO 2005/032501 , isoprenoids as described in WO 2005/102252 and in WO 2006/010661 , melanin derivatives such as Melasyn-100 and MelanZe, diacyl glycerols, aliphatic or cyclic diols, psoralens, prostaglandins and ana-logues thereof, activators of adenylate cyclase and compounds which activate the transfer of melanosomes to keratinocytes such as serine proteases or agonists of the PAR-2 receptor, extracts of plants and plant parts of the chrysanthemum species, san-guisorba species, walnut extracts, urucum extracts, rhubarb extracts, microalgae extracts, in particular Isochrysis gal- bana, trehalose, erythru-lose and dihydroxyacetone. Flavonoids which bring about skin and hair tinting or brown-ing (e.g. quercetin, rhamnetin, kaempferol, fisetin, genistein, daidzein, chrysin and api-genin, epicatechin, diosmin and diosmetin, morin, quercitrin, naringenin, hesperidin, phloridzin and phloretin) can also be used.
[00117] The amount of the aforementioned examples of Additional active ingredients for the modulation of skin and hair pigmentation (one or more compounds) in the prod- ucts according to the invention is then preferably 0.00001 to 30 wt.%, preferably 0.0001 to 20 wt.%, particularly preferably 0.001 to 5 wt.%, based on the total weight of the preparation. Hair growth activators or inhibitors
[00118] Formulations and products according to the present invention may also com- prise one or more hair growth activators, i.e. agents to stimulate hair growth. Hair growth activators are preferably selected from the group consisting of pyrimidine de- rivatives such as 2,4-diaminopyrimidine-3-oxide (Aminexil), 2,4-diamino-6-piperidino- pyrimidine-3-oxide (Minoxidil) and derivatives thereof, 6-amino-1 ,2-dihydro-1 -hydroxy- 2-imino-4-piperidinopyrimidine and its derivatives, xanthine alkaloids such as caffeine, theobromine and theophylline and derivatives thereof, quercetin and derivatives, dihy- droquercetin (taxifolin) and derivatives, potassium channel openers, antiandrogenic agents, synthetic or natural 5-reductase inhibitors, nicotinic acid esters such as to- copheryl nicotinate, benzyl nicotinate and C1 -C6 alkyl nicotinate, proteins such as for example the tripeptide Lys-Pro-Val, diphencypren, hormons, finasteride, dutasteride, flutamide, bicalutamide, pregnane derivatives, progesterone and its derivatives, cy- proterone acetate, spironolactone and other diuretics, calcineurin inhibitors such as FK506 (Tacrolimus, Fujimycin) and its derivatives, Cyclosporin A and derivatives thereof, zinc and zinc salts, polyphenols, procyanidins, proanthocyanidins, phytoster- ols such as for example beta-sitosterol, biotin, eugenol, (±)-beta-citronellol, panthenol, glycogen for example from mussels, extracts from microorganisms, algae, plants and plant parts of for example the genera dandelion (Leontodon or Taraxacum), Orthosi- phon, Vitex, Coffea, Paullinia, Theobroma, Asiasarum, Cucurbita or Styphnolobium, Serenoa repens (saw palmetto), Sophora flavescens, Pygeum africanum, Panicum miliaceum, Cimicifuga racemosa, Glycine max, Eugenia caryophyllata, Cotinus cog- gygria, Hibiscus rosa-sinensis, Camellia sinensis, Ilex paraguariensis, Isochrysis gal- bana, licorice, grape, apple, barley or hops or/nd hydrolysates from rice or wheat.
[00119] Alternatively, formulations and products according to the present invention may comprise one or more hair growth inhibitors (as described above), i.e. agents to reduce or prevent hair growth. Hair growth inhibitors are preferably selected from the group consisting of activin, activin derivatives or activin agonists, ornithine decarbox- ylase inhibitors such as alpha-difluoromethylornithine or pentacyclic triterpenes like for example ursolic acid, betulin, betulinic acid, oleanolic acid and derivatives thereof, 5al- pha-reductase inhibitors, androgen receptor antagonists, S-adenosylmethionine de- carboxylase inhibitors, gamma-glutamyl transpeptidase inhibitors, transglutaminase inhibitors, soybean-derived serine protease inhibitors, extracts from microorganisms, algae, different microalgae or plants and plant parts of for example the families Legu- minosae, Solanaceae, Graminae, Asclepiadaceae or Cucurbitaceae, the genera Chondrus, Gloiopeltis, Ceramium, Durvillea, Glycine max, Sanguisorba officinalis, Ca- lendula officinalis, Hamamelis virginiana, Arnica montana, Salix alba, Hypericum per- foratum or Gymnema sylvestre. Anti-inflammatory agents
[00120] Suitable anti-inflammatory agents may be selected from the group formed by:
(i) steroidal anti-inflammatory substances of the corticosteroid type, in particular hydrocortisone, hydrocortisone derivatives such as hydrocortisone 17-butyrate, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone,
(ii) non-steroidal anti-inflammatory substances, in particular oxicams such as pirox- icam or tenoxicam, salicylates such as aspirin, disalcid, solprin or fendosal, ace- tic acid derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin or clindanac, fenamates such as mefenamic, meclofenamic, flufenamic or niflumic, propionic acid derivatives such as ibuprofen, naproxen or be- noxaprofen, pyrazoles such as phenylbutazone, oxyphenylbutazone, febrazone or azapropazone,
(iii) natural or naturally occuring anti-inflammatory substances or substances that alleviate reddening and/or itching, in particular extracts or fractions from camo- mile, Aloe vera, Commiphora species, Rubia species, willow, willow-herb, oats, calendula, arnica, St John's wort, honeysuckle, rosemary, Passiflora incarnata, witch hazel, ginger or Echinacea, or single active compounds thereof,
(iv) histamine receptor antagonists, serine protease inhibitors (e.g. of Soy extracts), TRPV1 antagonists (e.g. 4-t-Butylcyclohexanol), NK1 antagonists (e.g. Aprepi- tant, Hydroxyphenyl Propamidobenzoic Acid), cannabinoid receptor agonists (e.g. Palmitoyl Ethanolamine) and TRPV3 antagonists.
Anti-microbial agents
[00121] Suitable anti-microbial agents are, in principle, all substances effective against Gram-positive bacteria, such as, for example, 4- hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4- dichlorophenyl)urea, 2,4,4'-trichloro-2'-hydroxy-di- phenyl ether (triclosan), 4-chloro-3,5-dimethyl-phenol, 2,2'-methylenebis(6-bromo-4- chlorophenol), 3-methyl-4-(1 -methylethyl)phenol, 2-benzyl-4-chloro-phenol, 3-(4-chlo- rophenoxy)-1 ,2-propanediol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'- trichlorocarbanilide (TTC), antibacterial fragrances, thymol, thyme oil, eugenol, oil of cloves, menthol, mint oil, farnesol, phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid N-alkylamides, such as, for example, n-octylsalicylamide or n- decylsalicylamide.
Enzyme inhibitors
[00122] Suitable enzyme inhibitors are, for example, esterase inhibitors. These are preferably trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and, in particular, triethyl citrate (Hydagen CAT). The substances inhibit enzyme activity, thereby reducing the formation of odour. Other substances which are suitable esterase inhibitors are sterol sulfates or phosphates, such as, for example, lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and esters thereof, such as, for example, glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and esters thereof, such as, for example, citric acid, malic acid, tartaric acid or diethyl tartrate, and zinc glycinate.
Odour absorbers and antiperspirant active agents
[00123] Suitable odour absorbers are substances which are able to absorb and largely retain odour-forming compounds. They lower the partial pressure of the individual com- ponents, thus also reducing their rate of diffusion. It is important that perfumes must remain unimpaired in this process. Odour absorbers are not effective against bacteria. They comprise, for example, as main constituent, a complex zinc salt of ricinoleic acid or specific, largely odour-neutral fragrances which are known to the person skilled in the art as "fixatives", such as, for example, extracts of labdanum or styrax or certain abietic acid derivatives. The odour masking agents are fragrances or perfume oils, which, in Addition to their function as odour masking agents, give the deodorants their respective fragrance note. Perfume oils which may be mentioned are, for example, mixtures of natural and synthetic fragrances. Natural fragrances are extracts from flow- ers, stems and leaves, fruits, fruit peels, roots, woods, herbs and grasses, needles and branches, and resins and balsams. Also suitable are animal products, such as, for example, civet and castoreum. Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol, and hydrocarbon type. Fragrance com- pounds of the ester type are, for example, benzyl acetate, p-tert-butylcyclohexyl ace- tate, linalyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, allyl cyclo- hexylpropionate, styrallyl propionate and benzyl salicylate. The ethers include, for ex- ample, benzyl ethyl ether, and the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal, the ketones include, for example, the ionones and methyl cedryl ketone, the alcohols include anethole, citronellol, euge- nol, isoeugenol, geraniol, linaool, phenylethyl alcohol and terpineol, and the hydrocar- bons include mainly the terpenes and balsams. Preference is, however, given to using mixtures of different fragrances which together produce a pleasing fragrance note. Es- sential oils of relatively low volatility, which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, camomile oil, oil of cloves, melissa oil, mint oil, cinnamon leaf oil, linden flower oil, juniperberry oil, vetiver oil, olibanum oil, galba- num oil, labdanum oil and lavandin oil. Preference is given to using bergamot oil, dihy- dromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, a-hexylcinnamaldehyde, gera- niol, benzylacetone, cyclamen aldehyde, linalool, boisambrene forte, ambroxan, in- dole, hedione, sandelice, lemon oil, mandarin oil, orange oil, allyl amyl glycolate, cy- clovertal, lavandin oil, clary sage oil, β damascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix coeur, iso-E-super, Fixolide NP, evernyl, iraldein gamma, phenyla- cetic acid, geranyl acetate, benzyl acetate, rose oxide, romilat, irotyl and floramat alone or in mixtures. [00124] Suitable astringent antiperspirant active ingredients are primarily salts of alu- minium, zirconium or of zinc. Such suitable antihydrotic active ingredients are, for ex- ample, aluminium chloride, aluminium chlorohydrate, aluminium dichlorohydrate, alu- minium sesquichlorohydrate and complex compounds thereof, e.g. with 1 ,2- propylene glycol, aluminium hydroxyallantoinate, aluminium chloride tartrate, aluminium zirco- nium trichlorohydrate, aluminium zirconium tetrachlorohydrate, aluminium zirconium pentachlorohydrate and complex compounds thereof, e.g. with amino acids, such as glycine.
Film formers and anti-dandruff agents
[00125] Standard film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone/vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyalu- ronic acid and salts thereof and similar compounds.
[00126] Suitable antidandruff agents are Pirocton Olamin (1 -hydroxy-4-methyl-6- (2,4,4-trimethylpentyl)-2-(1 H)-pyridinone monoethanolamine salt), Baypival® (Climba- zole), Ketoconazol® (4-acetyl-1 -{4-[2-(2,4-dichlorophenyl) r-2-(1 H-imidazol-1 -ylme- thyl)-1 ,3-dioxylan-c-4-ylmethoxyphenyl}-piperazine, ketoconazole, elubiol, selenium disulfide, colloidal sulfur, sulfur polyethylene glycol sorbitan monooleate, sulfur ricinol polyethoxylate, sulfur tar distillate, salicylic acid (or in combination with hexachloro- phene), undecylenic acid, monoethanolamide sulfosuccinate Na salt, Lamepon® UD (protein/undecylenic acid condensate), zinc pyrithione, aluminium pyrithione and mag- nesium pyrithione/dipyrithione magnesium sulfate.
Carriers and hydrotropes
[00127] Preferred cosmetics carrier materials are solid or liquid at 25°C and 1013 mbar (including highly viscous substances) as for example glycerol, 1 ,2-propylene glycol, 1 ,2-butylene glycol, 1 ,3-propylene glycol, 1 ,3-butylene glycol, ethanol, water and mix- tures of two or more of said liquid carrier materials with water. Optionally, these prep- arations according to the invention may be produced using preservatives or solubil- izers. Other preferred liquid carrier substances, which may be a component of a prep- aration according to the invention are selected from the group consisting of oils such as vegetable oil, neutral oil and mineral oil.
[00128] Preferred solid carrier materials, which may be a component of a preparation according to the invention are hydrocolloids, such as starches, degraded starches, chemically or physically modified starches, dextrins, (powdery) maltodextrins (prefera- bly with a dextrose equivalent value of 5 to 25, preferably of 10 - 20), lactose, silicon dioxide, glucose, modified celluloses, gum arabic, ghatti gum, traganth, karaya, carra- geenan, pullulan, curdlan, xanthan gum, gellan gum, guar flour, carob bean flour, algi- nates, agar, pectin and inulin and mixtures of two or more of these solids, in particular maltodextrins (preferably with a dextrose equivalent value of 15 - 20), lactose, silicon dioxide and/or glucose.
[00129] In Addition, hydrotropes, for example ethanol, isopropyl alcohol or polyols, may be used to improve flow behaviour. Suitable polyols preferably contain 2 to 15 carbon atoms and at least two hydroxyl groups. The polyols may contain other functional groups, more especially amino groups, or may be modified with nitrogen. Typical ex- amples are
• glycerol;
• alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propyl- ene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an av- erage molecular weight of 100 to 1000 Dalton;
• technical oligoglycerol mixtures with a degree of self-condensation of 1 .5 to 10, such as for example technical diglycerol mixtures with a diglycerol content of 40 to 50% by weight;
• methylol compounds such as, in particular, trimethylol ethane, trimethylol pro- pane, trimethylol butane, pentaerythritol and dipentaerythritol;
• lower alkyl glucosides, particularly those containing 1 to 8 carbon atoms in the alkyl group, for example methyl and butyl glucoside;
• sugar alcohols containing 5 to 12 carbon atoms, for example sorbitol or mannitol,
• sugars containing 5 to 12 carbon atoms, for example glucose or sucrose;
• amino sugars, for example glucamine;
• dialcoholamines, such as diethanolamine or 2-aminopropane-1 ,3-diol.
Preservatives and/or product protection agents
[00130] Suitable preservatives are, for example, phenoxyethanol, sodium benzoate or sorbic acid, blends of the mentioned ingredients and the other classes of compounds listed in Appendix 6, Parts A and B of the Kosmetikverordnung (“Cosmetics Directive”). Alternative products which could improve the product protection are for example 1 ,2- alkanediols such as for example 1 ,2-penatnediol, 1 ,2-hexanediol, 1 ,2-octanediol, 1 ,2- decanediol, 1 ,2-dodecanediol and mixtures thereof, 4-hydroxy acetophenone.
Dyes
[00131] Suitable dyes are any of the substances suitable and approved for cosmetic purposes as listed, for example, in the publication “Kosmetische Farbemittel” of the Farbstoffkommission der Deutschen Forschungsgemeinschaft, Verlag Chemie, Weinheim, 1984, pages 81 to 106. Examples include cochineal red A (C.l. 16255), patent blue V (C.l. 42051 ), indigotin (C.l. 73015), chlorophyllin (C.l. 75810), quinoline yellow (C.l. 47005), titanium dioxide (C.l. 77891 ), indanthrene blue RS (C.l. 69800) and mAder lake (C.l. 58000). Luminol may also be present as a luminescent dye. Advantageous coloured pigments are for example titanium dioxide, mica, iron oxides (e.g. Fe2O3 Fe3O4, FeO(OH)) and/or tin oxide. Advantageous dyes are for example carmine, Berlin blue, chromium oxide green, ultramarine blue and/or manganese vio- let.
Cosmetic preparations
[00132] Preferred compositions according to the present inventions are selected from the group of products for treatment, protecting, care and cleansing of the skin and/or hair or as a make-up product, preferably as a leave-on product (meaning that the one or more compounds stay on the skin and/or hair for a longer period of time, compared to rinse-off products).
[00133] The formulations according to the invention are preferably in the form of an emulsion, e.g. W/O (water-in-oil), O/W (oil-in-water), W/O/W (water-in-oil-in-water), O/W/O (oil-in-water-in-oil) emulsion, PIT emulsion, Pickering emulsion, emulsion with a low oil content, micro- or nanoemulsion, a solution, e.g. in oil (fatty oils or fatty acid esters, in particular C6-C32 fatty acid C2-C30 esters) or silicone oil, dispersion, suspen- sion, creme, lotion or milk, depending on the production method and ingredients, a gel (including hydrogel, hydrodispersion gel, oleogel), spray (e.g. pump spray or spray with propellant) or a foam or an impregnating solution for cosmetic wipes, a detergent, e.g. soap, synthetic detergent, liquid washing, shower and bath preparation, bath product (capsule, oil, tablet, salt, bath salt, soap, etc.), effervescent preparation, a skin care product such as e.g. an emulsion (as described above), ointment, paste, gel (as de- scribed above), oil, balsam, serum, powder (e.g. face powder, body powder), eau de perfume, eau de toilette, after-shave, a mask, a pencil, stick, roll-on, pump, aerosol (foaming, non-foaming or post-foaming), a deodorant and/or antiperspirant, mouth- wash and mouth rinse, a foot care product (including keratolytic, deodorant), an insect repellent, a sunscreen, aftersun preparation, a shaving product, aftershave balm, pre- and aftershave lotion, a depilatory agent, a hair care product such as e.g. shampoo (including 2-in-1 shampoo, anti-dandruff shampoo, baby shampoo, shampoo for dry scalps, concentrated shampoo), conditioner, hair tonic, hair water, hair rinse, styling creme, pomade, perm and setting lotion, hair spray, styling aid (e.g. gel or wax), hair smoothing agent (detangling agent, relaxer), hair dye such as e.g. temporary direct- dyeing hair dye, semi-permanent hair dye, permanent hair dye, hair conditioner, hair mousse, eye care product, make-up, make-up remover or baby product.
[00134] Auxiliary substances and additives can be included in quantities of 5 to 99 % b.w., preferably 10 to 80 % b.w., based on the total weight of the formulation. The amounts of cosmetic or dermatological auxiliary agents and additives and perfume to be used in each case can easily be determined by the person skilled in the art by simple trial and error, depending on the nature of the particular product.
[00135] The preparations can also contain water in a quantity of up to 99 wt.-percent., preferably from about 5 to about 80 wt.-percent and more preferably either from about 10 to about 50 or from about 60 to about 80 wt.-percent based on the total weight of the preparation.
ORAL COMPOSITIONS
[00136] Finally, another object of the present invention is directed to a preferably non- therapeutic oral and/or oral care composition. Typical examples for suitable oral com- positions encompass (hard boiled) candies, compressed tablets, chewing gums, tooth- pastes and mouth washes. The manufacture and composition of said oral composi- tions are described as follows:
Candies
[00137] According to the present invention the preferred candies are so-called hard boiled candies. Their bases are usually prepared from a mixture of sugar and other carbohydrates that are kept in an amorphous or glassy condition. This form can be considered a solid syrup of sugars generally having up to about 4.5 % b.w. moisture, based on the weight of the candy base, with about 0.5 to about 2.5 % b.w. being preferred and about 1 .0 to about 1 .5 % b.w. being most preferred. Such materials nor- mally contain up to 65 % b.w. corn syrup, up to 80 % b.w. sugar and from 0.1 to 5.0 % b.w. water. Generally, the ratio of sugar (or other sweetener suitable for candy formu- lation) to corn syrup is within the range of about 70:25 to about 45:55 with about 60:40 being preferred. The syrup component generally is prepared from corn syrups high in fructose, but may include other materials. Further ingredients such as flavourings, sweeteners, acidulents, colorants and so forth may also be added.
[00138] Hard boiled candy bases may also be prepared from non-fermentable sugars such as sorbitol, mannitol, xylitol, maltitol, hydrogenated starch hydrolysate, hydrogen- ated corn syrup and mixtures thereof. The candy bases may contain up to about 95% sorbitol, a mixture of sorbitol and mannitol at a ratio of about 9.5 to 0.5 up to about 7.5 to 2.5 and hydrogenated corn syrup up to about 55% of the syrup component.
Compressed tablets
[00139] According to the present invention the oral compositions can represent com- pressed tablets, comprising the liquid flavour in amounts of typically about 0.1 to about 0.6 % b.w. and preferably about 0.5 % b.w.
Chewing gums
[00140] Chewing gums typically consist of a water- insoluble vase component, a water- soluble component and additives providing for example a specific flavour.
[00141] The water-insoluble base, which is also known as the "gum base", typically comprises natural or synthetic elastomers, resins, fats and oils, plasticizers, fillers, sof- teners, dyes and optionally waxes. The base normally makes up 5 to 95% by weight, preferably 10 to 50% by weight and more particularly 20 to 35% by weight of the com- position as a whole. In one typical embodiment of the invention, the base consists of 20 to 60% by weight synthetic elastomers, 0 to 30% by weight natural elastomers, 5 to 55% by weight plasticizers, 4 to 35% by weight fillers, 5 to 35% by weight softeners and small amounts of additives, such as dyes, antioxidants and the like, with the pro- viso that they are soluble in water at best in small quantities.
[00142] Suitable synthetic elastomers are, for example, polyisobutylenes with average molecular weights (as measured by GPC) of 10,000 to 100,000 dalton and preferably 50,000 to 80,000 dalton, isobutylene/isoprene copolymers ("butyl elastomers"), sty- rene/butadiene copolymers (styrene:butadiene ratio, for example, 1 :3 to 3:1 ). polyvinyl acetates with average molecular weights (as measured by GPC) of 2,000 to 90,000 dalton and preferably 10,000 to 65,000 dalton, polyisoprenes, poly-ethylenes, vinyl ac- etate/vinyl laurate copolymers and mixtures thereof. Examples of suitable natural elas- tomers are rubbers, such as for example smoked or liquid latex or guayuls, and natural gums, such as jelutong, lechi caspi, perillo, sorva, massaranduba balata, massa- randuba chocolate, nispero, rosindinba, chicle, gutta hang kang and mixtures thereof. The choice of the synthetic and natural elastomers and their mixing ratios essentially depends on whether or not bubbles are to be produced with the chewing gums (bubble gums). Elastomer mixtures containing jelutong, chicle, sorva and massaranduba are preferably used.
[00143] In most cases, the elastomers are too hard or lack plasticity for satisfactory processing, so that it has been found to be of advantage to use special plasticizers which, of course, must also satisfy in particular all requirements relating to acceptability as food additives. In this respect, suitable plasticizers are, above all, esters of resin acids, for example esters of lower aliphatic alcohols or polyols with completely or partly hydrogenated, monomeric or oligomeric resin acids. In particular, the methyl, glycerol or pentaerythritol esters or mixtures thereof are used for this purpose. Alternatively, terpene resins, which may be derived from .alpha.-pinene, .beta.-pinene, .delta.-limo- nene or mixtures thereof, could also be used.
[00144] Suitable fillers or texturizers are magnesium or calcium carbonate, ground pumice stone, silicates, especially magnesium or aluminium silicates, clays, aluminium oxides, talcum, titanium dioxide, mono-, di- and tricalcium phosphate and cellulose polymers.
[00145] Suitable softeners or emulsifiers are tallow, hydrogenated tallow, hydrogen- ated or partly hydrogenated vegetable oils, cocoa butter, partial glycerides, lecithin, triacetin and saturated or unsaturated fatty acids containing 6 to 22 and preferably 12 to 18 carbon atoms and mixtures thereof.
[00146] Suitable dyes and Whiteners are, for example, the FD&C types, plant and fruit extracts permitted for colouring foods and titanium dioxide. The gum bases may also contain waxes or may be wax-free
[00147] In Addition to the water-insoluble gum base, chewing gum preparations regu- larly contain a water-soluble component which is formed, for example, by softeners, sweeteners, fillers, flavours, flavour enhancers, emulsifiers, dyes, acidifiers, antioxidants and the like, with the proviso that the constituents have at least adequate solubility in water. Accordingly, individual constituents may belong both to the water- insoluble phase and to the water-soluble phase, depending on the water solubility of the special representatives. However, combinations may also be used, for example a combination of a water-soluble and a water-insoluble emulsifier, in which case the in- dividual representatives are present in different phases. The water-insoluble compo- nent usually makes up 5 to 95% by weight and preferably 20 to 80% by weight of the preparation.
[00148] Water-soluble softeners or plasticizers are added to the chewing gum compo- sitions to improve chewability and the chewing feel and are present in the mixtures in quantities of typically 0.5 to 15% by weight. Typical examples are glycerol, lecithin and aqueous solutions of sorbitol, hydrogenated starch hydrolysates or corn sirup.
[00149] Fillers are particularly suitable for the production of low-calorie chewing gums and may be selected, for example, from polydextrose, raftilose, raftilin, fructo-oligosac- charides (NutraFlora), palatinose oligosaccharides, guar gum hydrolyzates (Sun Fiber) and dextrins.
[00150] The chewing gums may Additionally contain auxiliaries and additives which are suitable, for example, for dental care, more particularly for controlling plaque and gingivitis, such as for example chlorhexidine, CPC or triclosan. They may also contain pH adjusters (for example buffer or urea), anti-caries agents (for example phosphates or fluorides), biogenic agents (antibodies, enzymes, caffeine, plant extracts), providing these substances are permitted in foods and do not undesirably interact with one an- other.
Toothpastes and mouthwashes
[00151] Toothpastes or tooth creams are generally understood to be paste-like prepa- rations of water, thickeners, humectants, abrasives or polishes, surfactants, sweeten- ers, flavorings, deodorizing agents and agents active against oral and dental diseases. In toothpastes according to the invention, any of the usual polishes may be used, such as chalk, dicalcium phosphate, insoluble sodium metaphosphate, aluminium silicates, calcium pyrophosphate, finely particulate synthetic resins, silicas, aluminium oxide and aluminium oxide trihydrate. Particularly suitable polishes for toothpastes according to the invention are finely particulate xerogel silicas, hydrogel silicas, precipitated silicas, aluminium oxide trihydrate and finely particulate. alpha.-alumina, or mixtures of these polishes. Such polishes are preferably used in quantities of from about 15 to 40% by weight of the toothpaste. Preferred humectants used for toothpastes according to the invention include low molecular weight polyethylene glycols, glycerol, sorbitol or mix- tures thereof in quantities of up to about 50% by weight of the toothpaste. Among the known thickeners for use with toothpastes according to the invention, particularly pre- ferred are the thickening, finely particulate gel silicas and nonionic hydrocolloids, such as hydroxy ethyl cellulose, hydroxy propyl guar, hydroxy ethyl starch, polyvinyl pyrrolidone, high molecular weight polyethylene glycol and vegetable gums, such as tragacanth, agaragar, carrageen moss, gum arabic and xanthan gum. The desired fla- vor and aroma for preparations in accordance with the invention may be obtained by adding the components (a) and/or (b) and optionally also (c). It is also advantageous adding caries inhibitors to the oral preparations in the form of, for example, alkali fluo- rides, alkali monofluorophosphates or alkali salts of organophosphonic acids. In Addi- tion, the oral preparations according to the invention may contain other standard aux- iliaries, such as dyes, preservatives and opacifiers, for example titanium dioxide. For mouthwashes, the oral compositions according to the invention may readily be com- bined with aqueous-alcoholic solutions containing different amounts of ethereal oils, emulsifiers, astringent and toning drug extracts, caries-inhibiting additives and flavour correctants.
Additives
[00152] The oral compositions of the present invention may include additional additives as for examples sweeteners or vitamins, in amounts of from about 0.1 to about 10 % b.w. These additives may also represent components of the respective medicaments.
Sweeteners
[00153] Suitable sweet-tasting substances, including natural sources of these sub- stances (component e5), such as for example sweet-tasting carbohydrates or sugars (e.g. sucrose (synonymous with saccharose), trehalose, lactose, maltose, melizitose, raffinose, palatinose, lactulose, D-fructose, D-glucose, D-galactose, L-rhamnose, D- sorbose, D-mannose, D-tagatose, D-arabinose, L-arabinose, D-ribose, D-glyceralde- hyde, maltodextrin) or vegetable preparations containing predominantly these carbo- hydrates (e.g. from sugar beet, Beta vulgaris ssp., sugar fractions, sugar syrup, mo- lasses), from sugar cane (Saccharum officinarum ssp., e.g. molasses, sugar syrups), from sugar maple (Acer ssp.), from agave (agave thick juice), synthetic/enzymatic hy- drolysates of starch or sucrose (e.g. invert sugar syrup, highly enriched fructose syrups made from corn starch), fruit concentrates (e.g. from apples or pears, apple syrup, pear syrup), sugar alcohols (e.g. erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, mannitol, dulcitol, lactitol), proteins (e.g. miraculin, monellin, thaumatin, curculin, brazzein), sweeteners (magap, sodiumcyclamate, acesulfame K, neohesperidin dihydrochal- cone, saccharin sodium salt, aspartame®, superaspartame, neotame, alitame, su- cralose, stevioside, rebaudioside, lugduname, carrelame, sucrononate, sucrooctate, monatin, phyllodulcin), certain sweet-tasting amino acids (glycine, D-leucine, D-threo- nine, D-asparagine, D-phenylalanine, D-tryptophan, L-proline), other sweet-tasting low-molecular substances (e.g. hernandulcin, dihydrochalcone glycosides, glycyr- rhizin, glycyrrhetinic acid ammonium salt or other glycyrrhetinic acid derivatives), liq- uorice extracts (Glycyrrhizza glabra ssp.), Lippia dulcis extracts, Momordica ssp. ex- tracts or individual substances (in particular Momordica grosvenori [Luo Han Guo] and the mogrosides obtained therefrom), Hydrangea dulcis or Stevia ssp. (e.g. Stevia re- baudiana) extracts or individual substances.
Vitamins
[00154] In another embodiment of the present invention the compositions may include vitamins (component e1 ). Vitamins have diverse biochemical functions. Some have hormone-like functions as regulators of mineral metabolism (e.g., vitamin D), or regu- lators of cell and tissue growth and differentiation (e.g., some forms of vitamin A). Oth- ers function as antioxidants (e.g., vitamin E and sometimes vitamin C). The largest numbers of vitamins (e.g. B complex vitamins) act as precursors for enzyme cofactors that help enzymes in their work as catalysts in metabolism. In this role, vitamins may be tightly bound to enzymes as part of prosthetic groups: For example, biotin is part of enzymes involved in making fatty acids. Vitamins may also be less tightly bound to enzyme catalysts as coenzymes, detachable molecules that function to carry chemical groups or electrons between molecules. For example, folic acid carries various forms of carbon group - methyl, formyl, and methylene - in the cell. Although these roles in assisting enzyme-substrate reactions are vitamins' best-known function, the other vit- amin functions are equally important. In the course of the present invention suitable vitamins are selected from the group consisting of
Vitamin A (retinol, retinal, beta carotene),
Vitamin B1 (thiamine),
Vitamin B2 (riboflavin),
Vitamin B3 (niacin, niacinamide),
Vitamin B5 (panthothenic acid),
Vitamin B6 (pyridoxine, pyridoxamine, paridoxal),
Vitamin B7 (biotin),
Vitamin B9 (folic acid, folinic acid),
Vitamin B12 (cyanobalamin, hydoxycobalmin, methylcobalmin),
Vitamin C (ascorbic acid),
Vitamin D (cholecalciferol),
Vitamin E (tocopherols, tocotrienols), and
Vitamin K (phyolloquinone, menaquinone). [00155] The preferred vitamins are ascorbic acid and tocopherols. Said vitamins may be present in the food composition in amounts of about 0.1 to about 5 % b.w., and preferably about 0.5 to about 1 % b.w.
FOOD COMPOSITIONS
[00156] Food compositions according to the invention are any preparations or compo- sitions comprising the compositions according to the invention which are suitable for consumption and are used for nutrition or enjoyment purposes, and are generally prod- ucts which are intended to be introduced into the human or animal oral cavity, to remain there for a certain time and then either be eaten (e.g. ready-to-eat foodstuffs or feeds, see also herein below) or removed from the oral cavity again (e.g. chewing gums). Such products include any substances or products which in the processed, partially processed or unprocessed state are to be ingested by humans or animals. They also include substances which are added to orally consumable products during their man- ufacture, preparation or treatment and which are intended to be introduced into the human or animal oral cavity.
[00157] The food compositions according to the invention also include substances which in the unchanged, treated or prepared state are to be swallowed by a human or animal and then digested; in this respect, the orally consumable products according to the invention also include casings, coatings or other encapsulations which are to be swallowed at the same time or which may be expected to be swallowed. The expres- sion "orally consumable product" covers ready-to-eat foodstuffs and feeds, that is to say foodstuffs or feeds that are already complete in terms of the substances that are important for the taste. The expressions "ready-to-eat foodstuff" and "ready-to-eat feed" also include drinks as well as solid or semi-solid ready-to-eat foodstuffs or feeds. Examples which may be mentioned are frozen products, which must be thawed and heated to eating temperature before they are eaten. Products such as yoghurt or ice- cream as well as chewing gums or hard caramels are also included among the ready- to-eat foodstuffs or feeds.
[00158] Preferred food compositions according to the invention also include “semi-fin- ished products”. Within the context of the present text, a semi-finished product is to be understood as being an orally consumable product which, because of a very high con- tent of flavourings and taste-imparting substances, is unsuitable for use as a ready-to- eat orally consumable product (in particular foodstuff or feed). Only by mixing with at least one further constituent (e.g. by reducing the concentration of the flavourings and taste-imparting substances in question) and optionally further process steps (e.g. heat- ing, freezing) is the semi-finished product converted into a ready-to-eat orally consum- able product (in particular foodstuff or feed). Examples of semi-finished products which may be mentioned here are
[00159] Food composition according to the invention preferably comprises one or more preparations for nutrition or enjoyment purposes. These include in particular (reduced- calorie) baked goods (e.g. bread, dry biscuits, cakes, other baked articles), confection- ery (e.g. chocolates, chocolate bars, other products in bar form, fruit gums, dragées, hard and soft caramels, chewing gum), non-alcoholic drinks (e.g. cocoa, coffee, green tea, black tea, (green, black) tea drinks enriched with (green, black) tea extracts, rooi- bos tea, other herbal teas, fruit-containing soft drinks, isotonic drinks, refreshing drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks (e.g. instant cocoa drinks, instant tea drinks, instant coffee drinks), meat products (e.g. ham, fresh sausage or raw sausage preparations, spiced or marinated fresh or salt meat products), eggs or egg products (dried egg, egg white, egg yolk), cereal products (e.g. breakfast cereals, muesli bars, precooked ready-to-eat rice products), dairy prod- ucts (e.g. full-fat or reduced-fat or fat-free milk drinks, rice pudding, yoghurt, kefir, cream cheese, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, partially or completely hydrolysed milk-protein-containing products), products made from soy protein or other soybean fractions (e.g. soy milk and products produced there- from, drinks containing isolated or enzymatically treated soy protein, drinks containing soy flour, preparations containing soy lecithin, fermented products such as tofu or tempeh or products produced therefrom and mixtures with fruit preparations and op- tionally flavours), fruit preparations (e.g. jams, sorbets, fruit sauces, fruit fillings), veg- etable preparations (e.g. ketchup, sauces, dried vegetables, frozen vegetables, pre- cooked vegetables, boiled-down vegetables), snacks (e.g. baked or fried potato crisps or potato dough products, maize- or groundnut-based extrudates), fat- and oil-based products or emulsions thereof (e.g. mayonnaise, remoulade, dressings, in each case full-fat or reduced-fat), other ready-made dishes and soups (e.g. dried soups, instant soups, precooked soups), spices, spice mixtures and in particular seasonings which are used, for example, in the snacks field, sweetener preparations, tablets or sachets, other preparations for sweetening or whitening drinks or other foods. The preparations within the scope of the invention can also be used in the form of semi-finished products for the production of further preparations for nutrition or enjoyment purposes. The prep- arations within the scope of the invention can also be in the form of capsules, tablets (uncoated and coated tablets, e.g. enteric coatings), dragées, granules, pellets, solids mixtures, dispersions in liquid phases, in the form of emulsions, in the form of powders, in the form of solutions, in the form of pastes, or in the form of other preparations which can be swallowed or chewed, and in the form of food supplements.
[00160] The preparations can also be in the form of capsules, tablets (uncoated and coated tablets, e.g. enteric coatings), dragées, granules, pellets, solids mixtures, dis- persions in liquid phases, in the form of emulsions, in the form of powders, in the form of solutions, in the form of pastes, or in the form of other preparations which can be swallowed or chewed, for example in the form of food supplements.
[00161] The semi-finished products are generally used for the production of ready-to- use or ready-to-eat preparations for nutrition or enjoyment purposes.
[00162] Further constituents of a ready-to-eat preparation or semi-finished product for nutrition or enjoyment purposes can be conventional base substances, auxiliary sub- stances and additives for foods or enjoyment foods, for example water, mixtures of fresh or processed, vegetable or animal base or raw substances (e.g. raw, roast, dried, fermented, smoked and/or boiled meat, bone, cartilage, fish, vegetables, herbs, nuts, vegetable juices, vegetable pastes or mixtures thereof), digestible or non-digestible carbohydrates (e.g. sucrose, maltose, fructose, glucose, dextrins, amylose, amylopec- tin, inulin, xylans, cellulose, tagatose), sugar alcohols (e.g. sorbitol, erythritol), natural or hardened fats (e.g. tallow, lard, palm fat, cocoa fat, hardened vegetable fat), oils (e.g. sunflower oil, groundnut oil, maize germ oil, olive oil, fish oil, soya oil, sesame oil), fatty acids or their salts (e.g. potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (e.g. γ-aminobutyric acid, taurine), peptides (e.g. glutathione), natural or processed proteins (e.g. gelatin), enzymes (e.g. peptidases), nucleic acids, nucleotides, taste correctors for unpleasant taste impressions, further taste modulators for further, generally not unpleasant taste impressions, other taste- modulating substances (e.g. inositol phosphate, nucleotides such as guanosine mono- phosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), emulsifiers (e.g. lecithins, diacylglycerols, gum arabic), stabilisers (e.g. carrageenan, alginate), preservatives (e.g. benzoic acid and its salts, sorbic acid and its salts), antioxidants (e.g. tocopherol, ascorbic acid), chelators (e.g. citric acid), organic or inorganic acidifying agents (e.g. acetic acid, phosphoric acid), Additional bitter substances (e.g. quinine, caffeine, limonene, amarogentine, humu- lone, lupulone, catechols, tannins), substances that prevent enzymatic browning (e.g. sulfite, ascorbic acid), ethereal oils, plant extracts, natural or synthetic colourings or colouring pigments (e.g. carotinoids, flavonoids, anthocyans, chlorophyll and deriva- tives thereof), spices, trigeminally active substances or plant extracts containing such trigeminally active substances, synthetic, natural or nature-identical flavourings or odorants as well as odour correctors.
[00163] Food compositions according to the invention, for example those in the form of preparations or semi-finished products, preferably comprise a flavour composition in order to complete and refine the taste and/or odour. A preparation can comprise as constituents a solid carrier and a flavour composition. Suitable flavour compositions comprise, for example, synthetic, natural or nature-identical flavourings, odorants and taste-imparting substances, reaction flavourings, smoke flavourings or other flavour- giving preparations (e.g. protein (partial) hydrolysates, preferably protein (partial) hy- drolysates having a high arginine content, barbecue flavourings, plant extracts, spices, spice preparations, vegetables and/or vegetable preparations) as well as suitable aux- iliary substances and carriers. Particularly suitable here are the flavour compositions or constituents thereof which produce a roasted, meaty (in particular chicken, fish, sea- food, beef, pork, lamb, mutton, goat), vegetable-like (in particular tomato, onion, garlic, celery, leek, mushroom, aubergine, seaweed), spicy (in particular black and white pep- per, cardamom, nutmeg, pimento, mustard and mustard products), fried, yeast-like, boiled, fatty, salty and/or pungent flavour impression and accordingly can enhance the spicy impression. The flavour compositions generally comprise more than one of the mentioned ingredients.
[00164] The food compositions of the present invention are preferably selected from the group comprising
• confectionery, preferably reduced-calorie or calorie-free confectionery, preferably selected from the group comprising muesli bar products, fruit gums, dragées, hard caramels and chewing gum, • non-alcoholic drinks, preferably selected from the group comprising green tea, black tea, (green, black) tea drinks enriched with (green, black) tea extracts, rooi- bos tea, other herbal teas, fruit-containing low-sugar or sugar-free soft drinks, isotonic drinks, nectars, fruit and vegetable juices, fruit and vegetable juice prep- arations,
• instant drinks, preferably selected from the group comprising instant (green, black, rooibos, herbal) tea drinks,
• cereal products, preferably selected from the group comprising low-sugar and sugar-free breakfast cereals and muesli bars,
• dairy products, preferably selected from the group comprising reduced-fat and fat-free milk drinks, yoghurt, kefir, whey, buttermilk and ice-cream,
• products made from soy protein or other soybean fractions, preferably selected from the group comprising soy milk, products produced from soy milk, drinks con- taining isolated or enzymatically treated soy protein, drinks containing soy flour, preparations containing soy lecithin, products produced from preparations con- taining soy lecithin and mixtures with fruit preparations and optionally flavours,
• sweetener preparations, tablets and sachets,
• sugar-free dragées,
• ice-cream, with or without milk-based constituents, preferably sugar-free.
Sweeteners
[00165] The term "sweeteners" here denotes substances having a relative sweetening power of at least 25, based on the sweetening power of sucrose (which accordingly has a sweetening power of 1 ). Sweeteners to be used in an orally consumable product (in particular foodstuff, feed or medicament) according to the invention (a) are prefer- ably non-cariogenic and/or have an energy content of not more than 5 kcal per gram of the orally consumable product.
[00166] Advantageous sweeteners in a preferred orally consumable product (in partic- ular foodstuff, feed or medicament) according to the invention are selected from the following groups:
(a) Naturally occurring sweeteners, preferably selected from the group comprising miraculin, monellin, mabinlin, thaumatin, curculin, brazzein, pentaidin, D-phenyl- alanine, D-tryptophan, and extracts or fractions obtained from natural sources, comprising those amino acids and/or proteins, and the physiologically acceptable salts of those amino acids and/or proteins, in particular the sodium, potassium, calcium or ammonium salts, neohesperidin dihydrochalcone, naringin dihydro- chalcone, stevioside, steviolbioside, rebaudiosides, in particular rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, dulcosides and rubusoside, suavioside A, suavioside B, suavioside G, suavioside H, suavioside I, suavioside J, baiyunoside 1 , baiyunoside 2, phlomisoside 1 , phlomisoside 2, phlomisoside 3 and phlomi- soside 4, abrusoside A, abrusoside B, abrusoside C, abrusoside D, cyclocaryo- side A and cyclocaryoside I, osladin, polypodoside A, strogin 1 , strogin 2, strogin 4, selligueain A, dihydroquercetin 3-acetate, perillartin, telosmoside A15, perian- drin l-V, pterocaryosides, cyclocaryosides, mukuroziocides, trans-anethole, trans-cinnamaldehyde, bryosides, bryonosides, bryonodulcosides, carnosi- flosides, scandenosides, gypenosides, trilobatin, phloridzin, dihydroflavanols, he- matoxylin, cyanin, chlorogenic acid, albiziasaponin, telosmosides, gaudichaudi- oside, mogrosides, mogroside V, hernandulcins, monatin, phyllodulcin, glycyr- rhetinic acid and derivatives thereof, in particular glycosides thereof such as glycyrrhizine, and the physiologically acceptable salts of those compounds, in particular the sodium, potassium, calcium or ammonium salts; and extracts or concentrated fractions of the extracts, selected from the group com- prising thaumatococcus extracts (katamfe plant), extracts from Stevia ssp. (in particular Stevia rebaudiana), swingle extracts (Momordica or Siratia grosvenorii, Luo-Han-Guo), extracts from Glycerrhyzia ssp. (in particular Glycerrhyzia glabra), extracts from Flubus ssp. (in particular Flubus suavissimus), citrus extracts and extracts from Lippia dulcis;
(b) Synthetic sweet-tasting substances, preferably selected from the group compris- ing magap, sodium cyclamate or other physiologically acceptable salts of cyclamic acid, acesulfame K or other physiologically acceptable salts of acesul- fame, neohesperidin dihydrochalcone, naringin dihydrochalcone, saccharin, sac- charin sodium salt, aspartame, superaspartame, neotame, alitame, advantame, perillartin, sucralose, lugduname, carrelame, sucrononate and sucrooctate.
Thickeners
[00167] Advantageous thickeners in a preferred orally consumable product (in particu- lar foodstuff, feed or medicament) according to the invention are selected from the group comprising: crosslinked polyacrylic acids and derivatives thereof, polysaccha- rides and derivatives thereof, such as xanthan gum, agar-agar, alginates or tyloses, cellulose derivatives, for example carboxymethylcellulose or hydroxycarboxymethyl- cellulose, fatty alcohols, monoglycerides and fatty acids, polyvinyl alcohol and polyvi- nylpyrrolidone.
[00168] Preference is given according to the invention to an orally consumable product (in particular foodstuff or feed) which comprises milk thickened with lactic acid bacteria and/or cream thickened with lactic acid bacteria and which preferably is selected from the group comprising yoghurt, kefir and quark.
[00169] A food composition according to the invention comprising milk thickened with lactic acid bacteria and/or cream thickened with lactic acid bacteria is advantageously an orally consumable product which comprises a probiotic, wherein the probiotic is preferably selected from the group comprising Bifidobacterium animalis subsp. lactis BB-12, Bifidobacterium animalis subsp. lactis DN-173 010, Bifidobacterium animalis subsp. lactis HN019, Lactobacillus acidophilus LA5, Lactobacillus acidophilus NCFM, Lactobacillus johnsonii La1 , Lactobacillus casei immunitass/defensis, Lactobacillus ca- sei Shirota (DSM 20312), Lactobacillus casei CRL431 , Lactobacillus reuteri (ATCC 55730) and Lactobacillus rhamnosus (ATCC 53013).
Additives for chewing gums
[00170] Particular preference is given to an orally consumable product (in particular foodstuff, feed or medicament) according to the invention that is a chewing gum and comprises a chewing-gum base. The chewing-gum base is preferably selected from the group comprising chewing-gum or bubble-gum bases. The latter are softer, so that gum bubbles can also be formed therewith. Preferred chewing-gum bases according to the invention include, in Addition to the natural resins or the natural latex chicle that are traditionally used, elastomers such as polyvinyl acetate (PVA), polyethylene, (low or medium molecular weight) polyisobutene (PIB), polybutadiene, isobutene-isoprene copolymers (butyl rubber), polyvinyethyl ether (PVE), polyvinylbutyl ether, copolymers of vinyl esters and vinyl ethers, styrene-butadiene copolymers (styrene-butadiene rub- ber, SBR) or vinyl elastomers, for example based on vinyl acetate/vinyl laurate, vinyl acetate/vinyl stearate or ethylene/vinyl acetate, as well as mixtures of the mentioned elastomers, as described, for example, in EP 0 242 325, US 4,518,615, US 5,093,136, US 5,266,336, US 5,601 ,858 or US 6,986,709. In Addition, chewing-gum bases that are preferably to be used according to the invention preferably comprise further con- stituents such as, for example, (mineral) fillers, plasticisers, emulsifiers, antioxidants, waxes, fats or fatty oils, such as, for example, hardened (hydrogenated) vegetable or animal fats, mono-, di- or tri-glycerides. Suitable (mineral) fillers are, for example, cal- cium carbonate, titanium dioxide, silicon dioxide, talcum, aluminum oxide, dicalcium phosphate, tricalcium phosphate, magnesium hydroxide and mixtures thereof. Suitable plasticisers, or agents for preventing adhesion (detackifiers), are, for example, lanolin, stearic acid, sodium stearate, ethyl acetate, diacetin (glycerol diacetate), triacetin (glyc- erol triacetate), triethyl citrate. Suitable waxes are, for example, paraffin waxes, can- delilla wax, carnauba wax, microcrystalline waxes and polyethylene waxes. Suitable emulsifiers are, for example, phosphatides such as lecithin, mono- and di-glycerides of fatty acids, for example glycerol monostearate.
[00171] Chewing gums according to the invention (in particular as disclosed above) preferably comprise constituents such as sugars of different types, sugar substitutes, other sweet-tasting substances, sugar alcohols (in particular sorbitol, xylitol, mannitol), ingredients having a cooling effect, taste correctors for unpleasant taste impressions, further taste-modulating substances (e.g. inositol phosphate, nucleotides such as gua- nosine monophosphate, adenosine monophosphate or other substances such as so- dium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers, sta- bilisers, odour correctors and flavours (e.g. eucalyptus-menthol, cherry, strawberry, grapefruit, vanilla, banana, citrus, peach, blackcurrant, tropical fruits, ginger, coffee, cinnamon, combinations (of the mentioned flavours) with mint flavours as well as spearmint and peppermint on their own). The combination inter alia of the flavours with further substances that have cooling, warming and/or mouth-watering properties is of particular interest.
INDUSTRIAL APPLICATION
[00172] Another object of the present invention refers to a method for
• improving antimicrobial stability of a cosmetic or foodstuff preparation; and/or
• masking unpleasant flavors, particularly unpleasant flavors of fluorine deriva- tives and bitter compounds; and/or
• enhancing and/or boosting the performance of a flavor, a sweetener or a sooth- ing agent encompassing the step of adding a working amount of the composition according to the present invention to said preparation. Typically, the compositions are added in amounts of from 0.01 to 2 wt.-percent and preferably from about 0.1 to 1 wt.-percent - calculated on the preparations.
[00173] Also claimed is the use of the compositions according to the present invention for
• improving the antimicrobial stability of a cosmetic or foodstuff preparation; and/or
• masking unpleasant flavors, particularly unpleasant flavors of fluorine deriva- tives and bitter compounds; and/or
• enhancing and/or boosting the performance of a flavor, a sweetener or a sooth- ing agent.
[00174] For the sake of good order it is emphasized that all preferred embodiments, namely mixtures, compositions, ratio and the like also apply to the method and the use as claimed above. Therefore, any repetition is superfluous.
EXAMPLES
FORMULATION EXAMPLES FOR COSMETIC COMPOSITIONS [00175] The following examples F1 to F55 show various formulations for cosmetic compositions. “Composition 1 ” stands for any mixture of the preferred compounds (a) as cited in section [0037] with one of the compounds (b) to (d) or their mixtures.
Table F1 Liquid soap; transparent (Amounts in % b.w.)
Figure imgf000102_0001
Table F2
Syndet soap; liquid (Amounts in % b.w.)
Figure imgf000102_0002
Figure imgf000103_0003
Table F3
Cosmetic lotion for body wash (Amounts in % b.w.)
Figure imgf000103_0001
Table F4
Cosmetic lotion for body wash with Triclosan (Amounts in % b.w.)
Figure imgf000103_0002
Figure imgf000104_0001
Table F5
Intimate wash (Amounts in % b.w.)
Figure imgf000105_0001
Table F6
Liquid soap (Amounts in % b.w.)
Figure imgf000105_0002
Table F7
Shampoo (Amounts in % b.w.)
Figure imgf000106_0001
Table F8
2-in-1 Shampoo (Amounts in % b.w.)
Figure imgf000106_0002
Table F9
Anti-dandruff Shampoo (Amounts in % b.w.)
Figure imgf000107_0001
Table F10
Hair conditioner with Crinipan. rinse-off (Amounts in % b.w.)
Figure imgf000108_0001
Table F11
Sprayable hair conditioner with zinc pyrithrione. leave-on (Amounts in % b.w.)
Figure imgf000109_0001
Table F12
Hair conditioner with UV protection (Amounts in % b.w.)
Figure imgf000110_0001
Table 13
Shower gel (Amounts in % b.w.)
Figure imgf000110_0002
Table F14
Shaving foam (Amounts in % b.w.)
Figure imgf000111_0001
Table F15
Depilatory cream (Amounts in % b.w.)
Figure imgf000111_0002
Figure imgf000112_0001
Table F16
After Shave Tonic (Amounts in % b.w.)
Figure imgf000113_0001
Table F17
Deodorant formulation in the form of a roll-on gel (Amounts in % b.w.)
Figure imgf000113_0002
Table F18
Clear deo anti-perspirant roll-on (Amounts in % b.w.)
Figure imgf000114_0001
Table F19
Deodorant stick (Amounts in % b.w.)
Figure imgf000114_0002
Table F20
Zirconium suspensoid antiperspirant stick (Amounts in % b.w.)
Figure imgf000115_0001
Table F21
Deodorant pump spray with SymClariol (Amounts in % b.w.)
Figure imgf000115_0002
Figure imgf000116_0001
Table F22
Antiperspirant formulations (Amounts in % b.w.)
Figure imgf000116_0002
Table F23
Deodorant spray with Triclosan (Amounts in % b.w.)
Figure imgf000116_0003
Water | Ad 100
Table F24
O/W lotion (Amounts in % b.w.)
Figure imgf000117_0001
Table F25
Body lotion (Amounts in % b.w.)
Figure imgf000117_0002
Table F26
Cream (Amounts in % b.w.)
Figure imgf000118_0001
Table F27
Cream (Amounts in % b.w.)
Figure imgf000119_0001
Table F28
Hand and body cream (Amounts in % b.w.)
Figure imgf000120_0001
Table F29
Face cream (Amounts in % b.w.)
Figure imgf000121_0001
Table F30
Moisturizing body care cream (Amounts in % b.w.)
Figure imgf000122_0001
Table F31
Anti-wrinkle cream (Amounts in % b.w.)
Figure imgf000123_0001
Table F32
Functional skin oil for disinfection (Amounts in % b.w.)
Figure imgf000124_0001
Table F33
Septic wound cream (Amounts in % b.w.)
Figure imgf000125_0001
Table F34
Moisturizing and disinfecting face mask (Amounts in % b.w.)
Figure imgf000126_0001
Table F35
Sprayable disinfecting gel (Amounts in % b.w.)
Figure imgf000127_0001
Table F36
Mineral wash and cleaning gel (Amounts in % b.w.)
Figure imgf000128_0001
Table F37
Anti-acne wash (Amounts in % b.w.)
Figure imgf000129_0001
Table F38
Cosmetic sun protection composition (Amounts in % b.w.)
Figure imgf000130_0001
Table F39
Sun protection spray (Amounts in % b.w.)
Figure imgf000131_0001
Table F40
Sunscreen spray 0/W. SPE 15-20 (Amounts in % b.w.)
Figure imgf000132_0001
Table F41
Sun protection soft cream (W/O). SPF 40 (Amounts in % b.w.)
Figure imgf000133_0001
Table F42
Sun protection milk (W/O) (Amounts in % b.w.)
Figure imgf000134_0001
Table F43
After sun gel (Amounts in % b.w.)
Figure imgf000135_0001
Table F44
After sun lotion (Amounts in % b.w.)
Figure imgf000136_0001
Table F45
Hair styling gel (Amounts in % b.w.)
Figure imgf000136_0002
Table F46
Silicone emulsion (Amounts in % b.w.)
Figure imgf000137_0001
Table F47
Microemulsion gel (Amounts in % b.w.)
Figure imgf000137_0002
Table F48
Air freshener in gel form (Amounts in % b.w.)
Figure imgf000138_0001
Table F49
Cleaner. APC liquid, alkaline pH 8-10 (Amounts in % b.w.)
Figure imgf000138_0002
Table F50
Fabric softener (Amounts in % b.w.)
Figure imgf000138_0003
Figure imgf000139_0001
Table F51
Liquid detergent (Amounts in % b.w.)
Figure imgf000140_0001
Table F52
Liquid detergent concentrate (Amounts in % b.w.)
Figure imgf000140_0002
Table F53
Toilet cleaner (Amounts in % b.w.)
Figure imgf000141_0001
Table F54
Dish washing concentrate (Amounts in % b.w.)
Figure imgf000141_0002
Table F55
Dish washing concentrate (Amounts in % b.w.)
Figure imgf000142_0001
Table F56
Solution for wet wipes (Amounts in % b.w.)
Figure imgf000142_0002
Table F57
Chewing gum, free of sugar; all amounts in % b.w.
Figure imgf000143_0001
Table F58
Tooth paste; all amounts in % b.w.
Figure imgf000143_0002
Table F59
Mouth wash concentrate; all amounts in % b.w.
Figure imgf000144_0001
Table F60
Hard boiled candy, sugar-free; all amounts in % b.w.
Figure imgf000144_0002
Table F61 Hard boiled candy; all amounts in % b.w.
Figure imgf000144_0003

Claims

WHAT CLAIMED IS 1. A composition comprising or consisting of
(a) at least one benzoisoxazole derivative according to formula (I), a salt or a solvate thereof,
Figure imgf000145_0001
wherein - X is O and the dotted line represents a single bond; or - X is selected from CR3 and NR3, - wherein R3 is selected from hydrogen, C1-C6 alkyl, C1-C alkyl substi- tuted with one or two OH groups, C3-C7 cycloalkyl, C3-C7 cycloalkyl substituted with one or two OH groups, C5-C7 cycloalkenyl, C5-C7 cy- cloalkenyl substituted with one, two or three C1-C3 alkyl groups, and phenyl, and the dotted line represents a single bond or a double bond; - R1 is selected from hydrogen, - C1-C6 alkyl, - C1-C7 alkyl substituted with one or two OH groups, - C3-C7 alkenyl, - phenyl optionally substituted with up to five substituents selected from the group consisting of halogen, C=N, NO2, C1-C6 alkyl, C 1-C6 alkyl comprising up to 5 halogen atoms, C 1-C 6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms, C3-C7 cycloalkyl, -C(O)O- R10 wherein R10 is selected from hydrogen and C1-C3 alkyl, and - SR11 wherein R11 is selected from hydrogen and C1-C3 alkyl, naphtyl optionally substituted with up to five substituents selected from the group consisting of halogen, C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms, C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms, C3-C7 cycloalkyl, -C(O)O- R10 wherein R10 is selected from hydrogen and C1-C3 alkyl, and - SR 11 wherein R11 is selected from hydrogen and C1-C3 alkyl (includ- ing ethyl and isopropyl), and - C5-C10 mono-or bicyclic aryl wherein 1 or 2 C-atoms are replaced by a hetero atom independently selected from sulfur, nitrogen, and oxygen, optionally substituted with up to three substituents selected from the group consisting of halogen C=N, NO2, C1-C6 alkyl, C1-C6 alkyl com- prising up to 5 halogen atoms, C1-C6 alkyloxy, C1-C6 alkyloxy compris- ing up to 5 halogen atoms, C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is selected from hydrogen and C1-C6 alkyl, and -SR11 wherein R11 is selected from hydrogen and C1-C3 alkyl; - R2, R4, R5, and R7 are independently selected from hydrogen and C1- C6 alkyl; - R6 is selected from hydrogen, C1-C6 alkyl, and C3-C7 cycloalkyl; - R8 and R9 are independently selected from hydrogen, and C1-C6 alkyl, or - R8 and R9 form together with the C-atom to which they are attached a 3, 4, 5, 6, or 7-membered cycloalkyl ring; and - n is 0, or n is 1 and R’ is selected from hydrogen, C1-C6 alkyl, C2-C6 al- kyl substituted with one or two OH groups, C2-C6 alkenyl, or R’ forms together with the C-atom to which it is attached a carbonyl group (C=O);
(b) at least one physiological cooling or warming agent and/or
(c) at least one aroma or flavoring compound, and/or
(d) at least one fragrance whereby the compounds are present in a ratio by weight (a):(b+c+d) of from about 1 :1 ,500,000 to about 1 :1 2. The composition of Claim 1 comprising the compounds in a ratio by weight (a):(b+c+d) of from about 1 :1 ,500,000 to about 1 :10. 3. The composition of Claim 1 comprising the compounds in a ratio by weight (a):(b+c+d) of from about 1 :100,000 to about 1 :100. 4. The composition of Claim 1 comprising the compounds in a ratio by weight (a):(b+c+d) of from about 1 :40,000 to about 1 :500. 5. The composition of Claim 1 , wherein compound (a) represents at least one com- pound of formula (la), a salt or solvate thereof,
Figure imgf000147_0001
wherein - X is selected C and N; - R3 is selected from hydrogen, C1-C6 alkyl, C1-C7 alkyl substituted with one or two OH groups, C3-C7 cycloalkyl, C3-C7 cycloalkyl substituted with one or two OH groups, C5-C7 cycloalkenyl, C5-C7 cycloalkenyl substituted with one, two or three C1-C3 alkyl groups, and phenyl; - R1 is selected from hydrogen, - C1-C6 alkyl, - C1-C7 alkyl substituted with one or two OH groups, - C3-C7 alkenyl, - phenyl optionally substituted with up to five (e.g. one, two or three) substit- uents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O- R10 wherein R10 is selected from hydrogen and C1-C3 alkyl, and - SR11 wherein R11 is selected from hydrogen and C1- 3 alkyl (including ethyl and isopropyl), - naphtyl optionally substituted with up to five (e.g. one, two or three) substit- uents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O- R10 wherein R10 is selected from hydrogen and C1-C3 alkyl, and - SR11 wherein R11 is selected from hydrogen and C1-C3 alkyl (including ethyl and isopropyl), and - C5-C10 mono-or bicyclic aryl wherein 1 or 2 C-atoms are replaced by a het- ero atom independently selected from sulfur, nitrogen, and oxygen, option- ally substituted with up to three (e.g. 1 or 2) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1- C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is selected from hy- drogen and C1-C3 alkyl, and -SR11 wherein R11 is selected from hydrogen and C 1-C 3 alkyl (including ethyl and isopropyl); - R2, R4, R5, and R7 are independently selected from hydrogen and C1-C6 al- kyl; - R6 is selected from hydrogen, C1-C6 alkyl (e.g. ethyl, isopropy), and C3- C7 cycloalkyl; - R8 and R9 are independently selected from hydrogen, and C1-C6 alkyl, or - R8 and R9 form together with the C-atom to which they are attached a 3, 4, 5, 6, or 7-membered cycloalkyl ring. 6. The composition of Claim 1 , wherein compound (a) represents at least one com- pound of formula (lb), a salt or solvate thereof,
Figure imgf000148_0001
wherein - R1 is selected from hydrogen, - C1-C6 alkyl, - C1-C7 alkyl substituted with one or two OH groups, - C3-C7 alkenyl, - phenyl optionally substituted with up to five (e.g. one, two or three) substit- uents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O- R10 wherein R10 is selected from hydrogen and C1-C3 alkyl, and - SR11 wherein R11 is selected from hydrogen and C1-C3 alkyl (including ethyl and isopropyl), - naphtyl optionally substituted with up to five (e.g. one, two or three) substit- uents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1-C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C3-C7 cycloalkyl, -C(O)O- R10 wherein R10 is selected from hydrogen and C 1-C 3 alkyl, and - SR 11 wherein R11 is selected from hydrogen and C1-C3 alkyl (including ethyl and isopropyl), and - C5-C10 mono-or bicyclic aryl wherein 1 or 2 C-atoms are replaced by a het- ero atom independently selected from sulfur, nitrogen, and oxygen, option- ally substituted with up to three (e.g. 1 or 2) substituents selected from the group consisting of halogen (including Br, Cl, and F), C=N, NO2, C1-C6 alkyl, C1-C6 alkyl comprising up to 5 halogen atoms (including Br, Cl, and F), C1- C6 alkyloxy, C1-C6 alkyloxy comprising up to 5 halogen atoms (including Br, Cl, and F), C 3-C7 cycloalkyl, -C(O)O-R10 wherein R10 is selected from hy- drogen and C 1-C 3 alkyl, and -SR11 wherein R11 is selected from hydrogen and C1-C3 alkyl (including ethyl and isopropyl); - R3 is selected from hydrogen, C1-C6 alkyl, C1-C7 alkyl substituted with one or two OH groups, C3-C7 cycloalkyl, C3-C7 cycloalkyl substituted with one or two OH groups, C5-C7 cycloalkenyl, C5-C7 cycloalkenyl substituted with one, two or three C1-C3 alkyl groups, and phenyl; - R2, R4, R5, and R7 are independently selected from hydrogen and C1-C6 al- kyl; - R6 is selected from hydrogen, C1-C6 alkyl (e.g. ethyl, isopropy), and C3- C7 cycloalkyl; - R8 and R9 are independently selected from hydrogen, and C1-C6 alkyl, or - R8 and R9 form together with the C-atom to which they are attached a 3, 4, 5, 6, or 7-membered cycloalkyl ring. 7. The composition of Claim 1 , wherein compound (a) is selected from one or more of the following compounds:
• 1 , 3, 3, 5, 7-pentamethyl-5- (3-methylbut-2-en-1 -yl) octahydrobenzo [c] isoxazole;
• 1 , 3, 3, 5, 7-pentamethyl-5- (4-methylpyridin-3-yl) octahydrobenzo [c] isoxazole;
• 1 , 3, 3, 5, 7-pentamethyl-5- (pyridin-3-yl) octahydrobenzo [c] isoxazole;
• 1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazole;
• 1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazole hydrochloride;
• 1 , 3, 3, 6-tetramethyloctahydrobenzo [c] isoxazole;
• 1 , 3, 3-trimethyl-6- ((R) -4-methylcyclohex-3-en-1 -yl) octahydrobenzo [c] isoxazole;
• 1 , 5, 7-trimethylhexahydro-1 H-spiro [benzo [c] isoxazole-3, 1 '-cyclopen- tane]; 1 -ethyl-3, 3, 5, 7-tetramethyl-5- (3-methylbut-2-en-1 -yl) octahydrobenzo [c] isoxazole;
1 -isopropyl-3, 3, 5, 7-tetramethyl-5- (3-methylbut-2-en-1 -yl) octahydro- benzo [c] isoxazole;
1 -isopropyl-3, 3, 5, 7-tetramethyloctahydrobenzo [c] isoxazol-1 -ium chlo- ride;
1 -isopropyl-3, 3, 5, 7-tetramethyloctahydrobenzo [c] isoxazole;
1 -isopropyl-5, 7-dimethylhexahydro-1 H-spiro [benzo [c] isoxazole-3, 1 '- cyclopentane];
2- (1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzo- nitrile;
2-methyl-3- (1 , 3,
3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile;
5- (2,
4-dimethoxyphenyl) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazole;
5- (2, 5-dimethoxyphenyl) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazole;
5- (6-methoxypyridin-2-yl) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazole;
5, 7-diethyl-1 , 3, 3-trimethyloctahydrobenzo [c] isoxazole;
5-ethyl-1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazole;
6-isopentyl-1 , 4, 4, 8-tetramethyloctahydro-2H-benzo [d] [1 , 3] oxazin-2- one;
6-isopentyl-1 , 4, 4, 8-tetramethyloctahydro-2H-benzo [d] [1 , 3] oxazine; rac-(3aR, 5R, 7aR) -1 , 3, 3-trimethyl-5-pentyloctahydrobenzo [c] isoxa- zole; rac-(3aR, 5R, 7aR) -1 , 3, 3-trimethyl-5-propyloctahydrobenzo [c] isoxa- zole; rac-(3aR, 5R, 7aR) -1 -ethyl-3, 3-dimethyl-5-propyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7aR) -1 -isopropyl-3, 3-dimethyl-5-propyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7aR) -5-butyl-1 , 3, 3-trimethyloctahydrobenzo [c] isoxa- zole; rac-(3aR, 5R, 7aR) -5-butyl-1 -ethyl-3, 3-dimethyloctahydrobenzo [c] isox- azole; rac-(3aR, 5R, 7aR) -5-butyl-1 -isopropyl-3, 3-dimethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7aR) -5-ethyl-1 -isopropyl-3, 3-dimethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7R, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (2- (methylthio) phe- nyl) -octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7R, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyl-5- (3-methylbut-2- en-1 -yl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7R, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyl-5- (o-tolyl) octahy- drobenzo [c] isoxazole; rac-(3aR, 5R, 7R, 7aR) -5- (3-chloro-2-methylphenyl) -1 , 3, 3, 5, 7- pen- tamethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7R, 7aR) -5- (4-fluoro-2-methylphenyl) -1 , 3, 3, 5, 7-penta- methyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7R, 7aR) -5- (4-methoxyphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (2- (methylthio) phe- nyl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (2, 4, 5-trime- thylphenyl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (2-methyl-5- (trifluo- romethyl) phenyl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (4- (methylthio) phe- nyl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (5-methylthiophen-
2-yl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (5-methylthiophen-
3-yl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (m-tolyl) octahydro- benzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (naphthalen-1 -yl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (naphthalen-2-yl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (o-tolyl) octahydro- benzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5- (p-tolyl) octahydro- benzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5-phenyloctahydro- benzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl-5-propyloctahydro- benzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 7-tetramethyl-5- (3-methylbut-2-en-1 -yl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 7-tetramethyl-5- (o-tolyl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 , 3, 3, 7-tetramethyl-5-phenyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyl-5- (3-methylbut-2- en-1 -yl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyl-5- (o-tolyl) octahy- drobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyl-5-phenyloctahydro- benzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyloctahydrobenzo [c] isoxazole; rac- (3aR, 5R, 7S, 7aR) -1 -ethyl-5- (2-methoxyphenyl) -3, 3, 7-trime- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 5, 7-tetramethyl-5- (3-methyl- but-2-en-1 -yl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 5, 7-tetramethyl-5- (o-tolyl) oc- tahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 5, 7-tetramethyl-5-phenylocta- hydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 5, 7-tetramethyl-5-propyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 7-trimethyl-5- (3-methylbut-2- en-1 -yl) octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 7-trimethyl-5- (o-tolyl) octahy- drobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 7-trimethyl-5-phenyloctahydro- benzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-5- (2-methoxyphenyl) -3, 3, 5, 7-tet- ramethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-5- (2-methoxyphenyl) -3, 3, 7-trime- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-5- (4-methoxyphenyl) -3, 3, 5, 7-tet- ramethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -1 -isopropyl-5- (6-methoxypyridin-2-yl) -3, 3, 5, 7- tetramethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2, 3-dimethylphenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2, 4-difluorophenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2, 4-dimethylphenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2, 4-dimethylphenyl) -1 , 3, 3, 7-tetramethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2, 5-difluorophenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2, 5-dimethylphenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2, 5-dimethylphenyl) -1 , 3, 3, 7-tetramethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2, 6-dimethylphenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2-ethoxyphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2-ethylphenyl) -1 , 3, 3, 5, 7-pentamethyl- Octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2-ethylphenyl) -1 , 3, 3, 7-tetramethyloctahy- drobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2-ethylphenyl) -1 -isopropyl-3, 3, 7-trimethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2-fluorophenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2-methoxyphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (2-methoxyphenyl) -1 , 3, 3, 7-tetramethylocta- hydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (3, 4-difluorophenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (3, 5-difluorophenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (3, 5-dimethoxyphenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (3, 5-dimethylphenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (3, 5-dimethylphenyl) -1 -isopropyl-3, 3, 5, 7- tetramethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (3- chloro-2-methylphenyl) -1 , 3, 3, 5, 7-pen- tamethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (3-chloro-2-methylphenyl) -1 -isopropyl-3, 3, 7-trimethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (3-fluoro-5- (trifluoromethyl) phenyl) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (3-fluorophenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (3-isopropylphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (3-methoxyphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (4- (tert-butyl) phenyl) -1 , 3, 3, 5, 7-pentame- thyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (4- (tert-butyl) phenyl) -1 , 3, 3, 7-tetramethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (4- (tert-butyl) phenyl) -1 -isopropyl-3, 3, 7- trimethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (4-chloro-2-methylphenyl) -1 -isopropyl-3, 3, 7-trimethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (4-fluoro-2-methoxyphenyl) -1 , 3, 3, 5, 7-pen- tamethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (4-fluoro-2-methylphenyl) -1 , 3, 3, 5, 7-pen- tamethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (4-fluoro-2-methylphenyl) -1 , 3, 3, 7-tetra- methyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (4-fluorophenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (4-fluorophenyl) -1 -isopropyl-3, 3, 5, 7-tetra- methyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (4-methoxyphenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (5-chloro-2-methylphenyl) -1 , 3, 3, 5, 7-pen- tamethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (5-chloro-2-methylphenyl) -1 -isopropyl-3, 3, 7-trimethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (5-fluoro-2-methylphenyl) -1 , 3, 3, 5, 7-penta- methyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (5-fluoro-2-methylphenyl) -1 , 3, 3, 7-tetra- methyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (benzo [d] [1 , 3] dioxol-5-yl) -1 , 3, 3, 5, 7- pentamethyloctahydrobenzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5- (furan-3-yl) -1 , 3, 3, 5, 7-pentamethyloctahy- drobenzo [c] isoxazole; rac-3aR, 5R, 7S, 7aR) -5, 7-diethyl-1 -isopropyl-3, 3-dimethyloctahydro- benzo [c] isoxazole; rac-(3aR, 5R, 7S, 7aR) -5-isopentyl-1 -isopropyl-3, 3, 5, 7-tetramethyl- octahydrobenzo [c] isoxazole; rac-(3aR, 5S, 7aR) -1 , 3, 3, 5-tetramethyl-5- (3-methylbut-2-en-1 -yl) oc- tahydrobenzo [c] isoxazole; rac-(3aR, 7aR) -1 , 3, 3, 4, 5, 7-hexamethyloctahydrobenzo [c] isoxazole; rac-(3aR, 7aR) -1 , 3, 3-trimethyl-6-phenyloctahydrobenzo [c] isoxazole; rac-(3aR, 7aR) -1 , 5, 7-triethyl-3, 3- dimethyloctahydrobenzo [c] isoxa- zole; rac-(3aR, 7aS) -1 , 3, 3, 4, 5, 7-hexamethyloctahydrobenzo [c] isoxazole; rac-(3aR, 7S, 7aR) -5, 5-diethyl- 1 , 3, 3, 7-tetramethyloctahydrobenzo [c] isoxazole; rac-(3aS, 5R, 7S, 7aS) -5- (4-fluorophenyl) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazole; rac-(3aS, 5S, 7S, 7aS) -1 -ethyl-3, 3, 7-trimethyl-5- (3-methylbut-2-en-1 - yl) octahydrobenzo [c] isoxazole; rac-2-chloro-5- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydro- benzo [c] isoxazol-5-yl) benzonitrile; rac-2-chloro-5- ((3aS, 5R, 7R, 7aS) -1 , 3, 3, 5, 7-pentamethyloctahydro- benzo [c] isoxazol-5-yl) benzonitrile; rac-2-methyl-5- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydro- benzo [c] isoxazol-5-yl) benzonitrile; rac-3-((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile; rac-3-((3aR, 5R, 7S, 7aR) -1 -ethyl-3, 3, 5, 7-tetramethyloctahydrobenzo [c] isoxazol-5-yl) -4-methylbenzonitrile; rac-3-((3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 5, 7-tetramethyloctahydro- benzo [c] isoxazol-5-yl) -4-methylbenzonitrile; rac-3-((3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 5, 7-tetramethyloctahydro- benzo [c] isoxazol-5-yl) benzonitrile; rac-3-((3aR, 5R, 7S, 7aR) -1 -isopropyl-3, 3, 7-trimethyloctahydrobenzo [c] isoxazol-5-yl) -4-methoxybenzonitrile; rac-3-chloro-5- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethylocta-hydro- benzo [c] isoxazol-5-yl) benzonitrile; rac-3-methyl-4- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethylocta-hydro- benzo [c] isoxazol-5-yl) benzonitrile; rac-4- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydrobenzo [c] isoxazol-5-yl) benzonitrile; rac-4-methoxy-3- ((3aR, 5R, 7R, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahy- drobenzo [c] isoxazol-5-yl) benzonitrile; rac-4-methoxy-3- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahy- drobenzo [c] isoxazol-5-yl) benzonitrile; rac-4-methyl-2- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydro- benzo [c] isoxazol-5-yl) benzonitrile; rac-4-methyl-3- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydro- benzo [c] isoxazol-5-yl) benzonitrile; rac-4-methyl-3- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 7-tetramethyloctahydro- benzo [c] isoxazol-5-yl) benzonitrile; • rac-methyl 4-methyl-3- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyl- octahydrobenzo [c] isoxazol-5-yl) benzoate;
• rel-4-methyl-3- ((3aR, 5R, 7S, 7aR) -1 , 3, 3, 5, 7-pentamethyloctahydro- benzo [c] isoxazol-5-yl) benzonitrile and • rel-4-methyl-3- ((3aS, 5S, 7R, 7aS) -1 , 3, 3, 5,
7-pentamethyloctahydro- benzo [c] isoxazol-5-yl) benzonitrile. 8. The composition of Claim 1 , wherein said physiological cooling compounds form- ing group (b1) are selected from the group consisting of:
• Menthol
• Menthol glyceryl acetal
• Menthol glyceryl ketal
• Menthol menthyl ether
• Menthone glyceryl acetal
• Menthone glyceryl ketal
• Menthoxy-1 ,2-propandiol
• Menthoxy-2-methyl-1 ,2-propanediol
• Menthyl acetate
• Menthyl ethylene glycol carbonate
• Menthyl formiate
• Menthyl glutamate
• Menthyl glycerol carbonate
• Menthyl hydroxy isobutyrate
• Menthyl isobutyrate
• Menthyl lactate
• Menthyl malonate
• Menthyl methyl ether
• Menthyl N-ethyl oxamate
• Menthyl propylene glycol carbonate
• Menthyl pyroglutamate
• Menthyl-(2-methoxy)acetate
• Menthyl-(2-methoxyethoxy)acetate • Menthyl succinate
• O-Menthyl succinic acid ester amide
• O-Menthyl succinic acid ester-NN-(dimethyl)amide
• Menthane carboxylic acid-N-(4-cyanophenyl)amide
• Menthane carboxylic acid-N-(4-cyanomethylphenyl)amide
• Menthane carboxylic acid-N-ethylamide (WS-3)
• (WS-4)
• Nα-(menthane carbonyl) glycine ethylester (WS-5)
• (1 R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1 -isopropyl)cyclohex- ane-carboxamide (WS-12)
• (WS-14)
• 2,3-dimethyl-2-(2-propyl)-butyric acid-N-methylamide (WS23)
• Isopulegol acetate
• p-Menthane-3,
8-diol
• Cubebol
• 3-Methyl-2(1 -pyrrolidinyl)-2-cyclopentene-1 -one)
• Tetrahydropyrimidine-2-one
• N-(2-(pyridin-2-yl)ethyl)-3-p-menthanecarboxamide
• [(1 R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] 2-(ethylamino)-2-oxo- acetate
9. The composition of Claim 1 , wherein said physiological warming compounds forming group (b2) are selected from the group consisting of:
• vanillyl derivatives;
• capsaicin; • allyl isothiocyanate;
• gingerol;
• 4-(l-menthoxymethyl)-2-phenyl-l;3-dioxolan;
• 4-(l -menthoxymethyl)-2-(3';4'-dihydroxyphenyl)-l;3-dioxolan;
• 4-(l-menthoxymethyl)-2- (2'-hydroxy-3 '-methoxyphenyl)-3-dioxolan; • 4-(l-menthoxymethyl)-2-(4'-methoxyphenyl)-3-dioxolan;
• 4-(l-menthoxymethyl)-2-(3';4'methylenedioxyphenyl)-3 -dioxolan; • 4-(l-menthoxymethyl)-2-(3 ’-methoxy-4'-hydroxyphenyl) -3 -dioxolan;
• red pepper oil;
• red pepper oleoresin;
• ginger oleoresin; • nonylic acid vanillyl amide;
• jambu oleoresin;
• Zanthoxylum pieritum extract;
• sanshool I;
• sanshool II; • sanshoamide;
• black pepper extract;
• chavicine;
• piperine;
• spilanthol;
10. The composition of Claim 1 , wherein said flavors forming group (c) are selected from the group consisting of:
• 12-methyltridecanal;
• acetaldehyde;
• acetanisole;
• acethylthiazole-2;
• acethylthiazoline-2;
• acetic acid;
• acetyl methylcarbinol;
• acetyl pyrazine-2;
• acetyl pyridine-2;
• allyl capronate;
• allyl isothiocyanate;
• amyl cinnamaldehyde-alpha;
• anethole; anisaldehyde-para; anisic alcohol; benzaldehyde; benzyl acetate; borneol-l; butyl acetate; butylidene phthalide-3; butyric acid; camphor; caproic acid; carvacrol; carvomenthone; carvo n-d; carvon-l; carvylacetate-cis; caryophyllene; cineole-1 ;4; cineole-1 ;8; cinnamalcohol; cinnamaldehyde; cinnamyl acetate; citral; citronellal; citronellol; citronellyl acetate; cresol cuminaldehyde; cyclopentadecanolide; damascenone-alpha; damascenone-beta; damascone-alpha; damascoe-beta; decadienal-2;4; decadienal-2;4; decalactone delta; decalacton gamma; decanal; dehydromenthofurolactone; diallyl disulfide; diethylpyrazine-2;3; dihydroanethol; dihydrocarvone; dihydrocoumarin; dihydroionone-beta; dihydromenthofurolactone; dihydronootkatone; dimethyl lanthranilate; dimethyl isopropyldithiazine; dimethyl pyrazine; dimethyl sulfide; diphenyloxide; divanilline; d-menthol; d-menthone; d-menthyl acetate; dodecalactone-delta; dodecalactone-gamma; epithiomenthan-1 ;8; ethyl acetate; ethyl butyrate; ethyl capronate; ethyl caprylate; ethyl cinnamate; ethyl isobutyrate; ethyl isovaleria-nate; ethyl lactate; ethyl maltol; ethyl methyl butyrate-2; ethyl methyl thiopropionate; ethyl phenol-4; ethyl vanillin; eugenol; fenchol; filbertone; frambinone methyl ether; frambinone; furaneol; furfurylthiol; geraniol; geranyl acetate; geranyl isobutyrate; guaiacol; heliotropin; heptalactone-gamma; heptanone-2; heptenal-Z-4; hexalactone-gamma; hexanal hexanol; hexenol-E-2; hexenol-Z-3; hexenyl acetate-E-2; hexenyl acetate-Z-3; hexenyl capronate-Z-3; hexyl acetate; hexyl cinnamaldehyde-alpha; hotrienol; indole; ionon-beta; ionone-alpha; isoamyl acetate; isoamyl butyrate; isoamyl isovaerianate; isobutyl acetate; isobutyl thiazole; isobutylmethoxypyrazine isobutyraldehyde; isoeugenol;
Isomenthon; isopropylmethoxypyrazine; isopropylmethylpyrazine-2;4; isopulegol; isova-leraldehyde; jasmine lactone; jasmon cis; ketoisophorone; limonene-d; linalool oxide; linalool-d; linalool-l; linalyl acetate; l-menthol; l-menthone; l-menthyl acetate; maltol; massoilactone; melonal; menthadienyl acetate; menthofurolactone; menththiol-1 ;8; methional; methoxymethylpyrazine-2;3; methyl anthranilate; methyl butyl acetate-2; methyl butyrate; methyl cinnamate; methyl dihydrojasmonate; methyl furanthiol-2;3; methyl jasmonate; methyl salicylate; methyl tetrahydrofuranthiol-2;3; methyl thiobutyrate; methyl thiohexyl acetate-1 ;3; methylcyclopen-tenolone; methylthiohexanol-1 ;3; myrtenal; naringin; neo-menthol; neral; nerol; nerylacetate; nonadienal-2;4; nonadienal-2;6; nonalactone delta; nonalactone gamma; nonenal-E-2; nonenal-Z-6; nonenol-Z-6; nootkatone; octalactone gamma; octalactone delta; octanal octenol-1 ;3; pellitorin; pentenone-1 ;3; pentyl acetate; phenyl ethyl acetate; phenyl ethyl alcohol; phenyl acetaldehyde; pinene-alpha; pinene-beta; piperitanate; piperitone prenyl thioacetate; prenyl thiol; reubenamine; rose oxide; rubescenamine; sabinene hydrate; scatole; sotolone; styrolyl acetate; terpinenol-4; terpineol; thiohexanol-1 ;3; thiohexyl acetate-1 ;3; thiomenthanone-8;3; thiopentanone-4;4;2; thymol; tridecatrienal; trimethyl pyrazine; undecadienal-2;4; undecalactone-gamma and delta; undecatriene; vanillin; vinyl guaiacol; • whisky lactone;
11. The composition of Claim 1 , wherein said fragrances forming group (d) are se- lected from the group consisting of:
• [(3,7-dimethyl-6-octenyl)-xy]-acetaldehyde,
• 1 -(p-menthene-6(2)-yl)-1 -propanone,
• 1 ,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthaldehyde,
• 10-undecen-1 -al,
• 10-undecen-1 -ol,
• 1 -decanal,
• 1 -dodecanal,
• 1 -methyl-3-(4-methylpentyl)-3-cyclohexene-carboxyaldehyde,
• 1 -methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1 -carboxaldehyde,
• 1 -nonanal,
• 1 -octanal,
• 1 -octen-3-ol,
• 1 -p-menthene-q-carboxaldehyde,
• 1 -undecanal,
• 2-(2-(4-Methyl-3-cyclohexen-1 -yl)propyl)-cyclopentanone,
• 2,4,4,7-tetramethyl-oct-6-en-3-one,
• 2,4,6-trimethyl-3-cyclohexene-l-carboxalde-hyde,
• 2, 4-dimethyl-3-cyclohexen-1 -carboxaldehyde 4-methoxybenzalde- hyde,
• 2,4-dimethyl-3-cyclohexen-1 -carboxyaldehyde,
• 2,6,10-trimethyl-5,9-undecadienal,
• 2,6,10-trimethyl-9-undecenal, 3-dodecen-1 -al,
• 2,6-dimethyl-5-heptenal;
• 2,6-dimethylhept-5-en-1 -al,
• 2,6-dimethylheptan-2-ol,
• 2,6-nonadienal,
• 2-acetyl-3,3-di-methyl-norbornan,
• 2-methyl decanal, • 2-methyl octanal, • 2-methyl undecanal, • 2-methyl-3-(4-tertbutyl)propanal, • 2-methyl-3-(isopropyl-phenyl)propanal, • 2-methyl-3-(para-methoxy-phenylpropanal), • 2-methyl-3-phenyl-2-propen-1 -al, • 2-methyl-4-(2,6,6-trimethyl-1 -cyclohexen-1 -yl)-2-butenal, • 2-methylbutanol, • 2-methylpentanol, • 2-phenoxyethanol, • 2-phenylpropan-1 -al, • 2-phenylpropanol, • 2-tert-butycyclohexanol, • 3-(3,4-methylendioxy-phenyl)-2-methylpropan-1 -al, • 3-(3-isopropylphenyl)-butan-1 -al, • 3-(4-ethylphenyl)-2,2-dimethylpropan-1 -al, • 3-(4-ethylphenyl)-2,2-dimethylpropanal, • 3-(4-isopropylphenyl)-2-methylpropan-1 -al, • 3-(4-methoxyphenyl)-2-methylpropanal, • 3-(4-tert-butylphenyl)-2-methyl-propanal, • 3-(4-tert-butylphenyl)-propanal, • 3,4-dimethoxybenzaldehyde, • 3,4-methylendioxybenzaldehyde, • 3,5,5-trimethylcyclohexanol, • 3,5,5-trimethylhexanal, • 3,5,6-trimethyl-3-cyclohexenecarboxaldehyde, • 3,7-dimethyl-2-methylene-6-octenal, • 3 3,7-dimethyl-6-octen-1 -al, • 3,7-dimethyloctan-1 -al, • 3-ethoxy-4-hydroxybenzaldehyde, • 3-hexanol,
• 3-methoxy-4-hydroxy-benzaldehyde,
• 3-methyl-5-phenyl-1 -pentanal,
• 3-methyl-5-phenylpentanol,
• 3-octanol,
• 3-phenyl-2-hexylprop-2-enal,
• 3-phenyl-2-pentylprop-2-en-1 -al,
• 3-phenyl-2-propenal,
• 3-phenylprop-2-en-1 -al,
• 3-phenylpropanol,
• 3-propyl-bicyclo[2.2.1 ]-hept-5-ene-2-carbaldehyde,
• 4-(1 -ethoxyvinyl)-3,3,5,5-tetramethyl cyclohexanone,
• 4-(3)(4-methyl-3-pentenyl)-3-cyclohexen-carboxaldehyde,
• 4-(4-hydroxy-3-methoxyphenyl)-2-butanone,
• 4-(4-hydroxy-4-methylpentyl)-3-cylohexene-l-carboxal-dehyde,
• 4-(tricyclo[5.2.1 ,0(2,6)]-decylidene-8)-butanal;
• 4-damascol,
• 4-heptenol,
• 4-hydroxy acetophenone
• 4-hydroxy-3-methoxybenzaldehyde,
• 4-isopropyl benzyaldehyde,
• 4-isopropyl cyclohexanol,
• 4-methoxy benzaldehyde,
• 4-methylphenyl acetaldehyde,
• 4-tert-butyl cyclohexanol,
• 5,9-dimethyl-4,8-decadienal,
• 5-methoxyhexahydro-4,7-methanoindan-1 -carboxyaldehyde,
• 5-methoxyhexahydro-4,7-methanoindan-2-carboxyaldehyde,
• 6,10-dimethyl-3-oxa-5,9-undecadien-1 -al,
• 6,6-dimethyl-2-norpinene-2-propionaldehyde, • 6,7-dihydro-1 ,1 ,2,3,3-pentamethyl-4(5H)-indanone,
• 6,8-dimethyl-2-nonanol,6-nonen-1 -ol ,
• 6-isopropyl-deca-hydro-2-naphtone,
• 6-methoxyhexahydro-4,7-methanoindan-1 -carboxyaldehyde,
• 6-methoxyhexahydro-4,7-methanoindan-2-carboxyaldehyde,
• 7-hydroxy-3,7-dimethyl octanal,
• 7-methoxy-3,7-dimethyloctan-1 -al,
• 9-decen-1 -ol,
• 9-decenal,
• acetophenone,
• adoxal,
• allyl cyclohexylpropionate,
• alphalonen,
• ambroxan,
• amylsalicylat,
• anethol,
• anisaldehyde,
• benzaldehyde,
• benzophenone,
• benzyl acetate,
• benzyl acetone,
• benzyl alcohol,
• benzyl salicylate,
• benzylethyl ether,
• bourgeonal,
• buccoxime,
• butyl lactate
• butyl salicylate,
• campher,
• canthoxal, • carvone,
• cassione,
• celery cetone
• chlorhydral,
• cinnamalcohol,
• cis-/trans-3,7-dimethyl-2,6-octadien-1 -al,
• cis-jasmon,
• citral or its mixtures,
• citronellal,
• citronellol,
• citronellyl oxyacetaldehyde,
• cumal,
• cyclamenaldehyde,
• cyclohexyl salicylate,
• cymal,
• damarose,
• damascenone,
• decanol,
• decyl aldehyde,
• delphone,
• dihydrojasmone,
• dihydromyrcenol,
• dihydrozimtaldehyde,
• dihydro-β -lonone,
• dimethyl benzylcarbinol,
• dimethyl benzylcarbinylacetate,
• dimethyl heptanol,
• dimethyl octanol,
• dimethyl octenone,
• dulcinyl • ethyl salicylate,
• ethyl vanilin,
• ethylmethylphenyl glycinate,
• eugenol,
• fenchone,
• fleuramone,
• floralozon,
• floramat,
• florhydral,
• gelsone,
• geraniol,
• hedione,
• helional,
• heliotropin,
• heptanol,
• hexahydro-4, 7-methanoindan-1 -carboxaldehyde,
• hexahydro-8, 8-dimethyl-2-naphthaldehyde,
• hexalone,
• hexyl salicylat,
• hydroxycitronellal,
• isoborneol,
• isodamascone,
• isoeugenol,
• isojasmone,
• isopulegol,
• jasmacyclatat,
• koavon,
• laurinaldehyde,
• ligustral,
• lilial citral, • lilial,
• limonen,
• linalool,
• linalyl acetate,
• livescon,
• lyral,
• m-cymene-7-carboxaldehyde,
• melonal,
• melusat,
• menthol,
• menthone,
• methyl acetophenone,
• methyl cedrenyl ketone,
• methyl cedrylon,
• methyl cedrylone,
• methyl cyclocitrone,
• methyl dihydrojasmonate,
• methyl heptenone,
• methyl lavender ketone,
• methyl-dihydrojasmonate,
• methylnonyl acetaldehyde,
• methyl-β-naphthyl ketone,
• moschus indanone,
• muscone,
• myrtenol,
• n-dodecanal,
• neobutenone,
• nerol,
• n-hexanol,
• nonanol, • n-undecanal, • octahydro-4,7-methano-1 H-indenecarboxaldehyde; • octanal, • octanol, • o-methoxyzimtaldehyde, • orivone, • p-ethyl-α,α-dimethylhydrozimtaldehyde, • phenol, • phenoxyacetaldehyde; • phenoxyisobutyrate, • phenyl acetaldehyde, • phenyl salicylat, • phenylethyl acetate, • phenylethyl alcohol, • phenylpropyl alcohol • p-hydroxy phenylbutanone, • pinen • plicatone, • p-menthan-7-ol, • p-methoxy acetophenone, • p-methyl phenoxy acetaldehyde, • p-tert.-bucinal, • p-tert.-butyl cyclohexanone, • p-tert.-butyl cyclohexylacetate, • p-tolyl acetaldehyde; • styrallyl propionate, • tetrahydrogeraniol, • tetrahydrolinalool, • tetrameran, • thymol, • tonalid/moschus plus,
• trans-2-cis-6-nonadienol,
• trans-2-nonen-1 -ol,
• trans-2-octenol,
• trans-4-decenal,
• triplal,
• undecanal,
• undecanol,
• undecylenraldehyde,
• vanillin,
• veloutone,
• verdone,
• α.-methyl-3,4-(methylenedioxy)-hydrocinnamaldehyde,
• α-damascone,
• α-methyl benzylalcohol,
• α-methyl-4-(l-methylethyl)benzene-acetaldehyde,
• α-methylphenylacetaldehyde,
• αn-Amylzimtaldehyde,
• α-n-hexyl-cinnamaldehyde,
• α-terpineol,
• β-damascone,
• β-ionon,
• β-terpineol,
• γ-methylionone,
• δ-damascone,
12. A cosmetic preparation comprising the composition of Claim 1 .
13. The preparation of Claim 9 representing a skin care, personal care, hair care, sun care or oral care preparation.
14. The preparation of Claim 9, comprising the composition of Claim 1 in amounts of from about 0.01 to 1 wt.-percent - calculated on the preparation.
15. A foodstuff preparation comprising the composition of Claim 1 .
16. The preparation of Claim 12, comprising the composition of Claim 1 in amounts of from about 0.01 to 1 wt.-percent - calculated on the preparation.
17. A method for improving antimicrobial stability of a cosmetic or foodstuff prepara- tion encompassing the step of adding a working amount of the composition of Claim 1 to said preparation.
18. A method for masking unpleasant flavors, particularly unpleasant flavors of fluo- rine derivatives and bitter compounds encompassing the step of adding a working amount of the composition of Claim 1 to said preparation.
19. A method for enhancing and/or boosting the performance of a flavor, a sweetener or a soothing agent encompassing the step of adding a working amount of the composition of Claim 1 to said preparation.
20. The use of the composition of Claim 1 for improving the antimicrobial stability of a cosmetic or foodstuff preparation.
21. The use of the composition of Claim 1 for masking unpleasant flavors, particularly unpleasant flavors of fluorine derivatives and bitter compounds.
22. The use of the composition of Claim 1 for enhancing and/or boosting the perfor- mance of a flavor, a sweetener or a soothing agent.
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