EP2864287A1 - Photolabile duftspeicherstoffe - Google Patents
Photolabile duftspeicherstoffeInfo
- Publication number
- EP2864287A1 EP2864287A1 EP13721307.0A EP13721307A EP2864287A1 EP 2864287 A1 EP2864287 A1 EP 2864287A1 EP 13721307 A EP13721307 A EP 13721307A EP 2864287 A1 EP2864287 A1 EP 2864287A1
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- European Patent Office
- Prior art keywords
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- radical
- substituted
- weight
- atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
- C11D3/507—Compounds releasing perfumes by thermal or chemical activation
Definitions
- the present invention relates to specific cationically charged compounds which function as photolabile fragrance storage materials. Furthermore, the present invention relates to detergents or cleaners, cosmetics and room fragrancing agents containing such compounds. It also relates to a process for the long-lasting scenting of surfaces and also to a process for long-lasting scenting of the room.
- Detergents or cleaners or cosmetic products usually contain fragrances that give the products a pleasant smell. In most cases, the fragrances mask the odor of the other ingredients, resulting in a pleasant odor impression for the consumer.
- Fragrances are important constituents of the composition, in particular in the area of detergents, since the laundry should have a pleasant and if possible fresh fragrance both in the moist and in the dry state.
- fragrances When it comes to the use of fragrances, one generally faces the problem that these are more or less volatile compounds, but nevertheless a long-lasting fragrant effect is desired.
- Delayed fragrance release may be e.g. carried out by carrier-bound use of fragrances.
- a carrier-bound perfume preform is also referred to as a "pro-fragrance" or fragrance storage material
- International Patent Application WO 2007/087977 discloses the use of 1-aza-3,7-dioxabicyclo [3.3.0] octane compounds
- An alternative possibility of delayed release of fragrances is the use of so-called photoactivatable substances as fragrance storage substances.
- the action of sunlight or another electromagnetic radiation source of a specific wavelength causes the break of a covalent bond in the fragrance storage molecule, thereby releasing a fragrance.
- WO 201 1/101 180 discloses the use of certain ketones as photoactivatable substances which release an active substance in the presence of light in a photochemical fragmentation.
- the active substance mentioned has, for example, a fragrant activity, which is delayed by the photochemically induced decomposition and released over a longer period of time on a certain surface.
- the object of the present invention was to provide photoactivatable substances as fragrance storage substances which permit the delayed release of perfume ketones and perfume esters and which are particularly readily applied to surfaces, in particular to textile surfaces.
- R is a substituted hydrocarbon radical having 2 to 20 C atoms, which has at least one carbonyl group or ester group,
- R 1, R 2 each independently represent hydrogen, a linear or branched, substituted or unsubstituted alkoxy group having 1 to 15 C atoms, a linear or branched, substituted or unsubstituted alkyl group or alkenyl group having 1 to 15 C atoms or a substituted or unsubstituted one Aryl radical,
- R 3 , R 4, R 5, R 6 and R 7 each independently represent hydrogen, an amino group, -NO 2 , a linear or branched, substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, a linear or branched, substituted or unsubstituted alkyl group with 1 to 15 C atoms, a cycloalkyl radical, acyl radical, aryl radical, -OH, -NH 2 , halogen, NH-alkyl or -N (alkyl) 2 ,
- the compounds of the invention are particularly effective fragrance storage materials, which are particularly good on surfaces, especially on textile surfaces, raise.
- the use of quaternary ammonium radicals of the formula (II) in compounds of the formula (I) has the effect that the compounds according to the invention are particularly effective fragrance-based storage substances and are particularly readily applied to surfaces, in particular textile surfaces.
- the compounds according to the invention enable the sustained release of perfume ketones, in particular of damascones or of perfume esters, in particular cinnamic acid esters and derivatives of cinnamic acid esters.
- the use of the compounds according to the invention in detergents, cleaners or care products resulted in their use in an improved long-term odor effect, in particular in connection with the textile treatment.
- compositions according to the invention make it possible to reduce the total amount of perfume which is contained on average, and nevertheless to achieve odor advantages on the laundered textiles, in particular with regard to the sensation of freshness.
- the compound according to the general formula (I) is suitable as a fragrance storage substance for all customary fragrance ketones and fragrance esters which, in their free form as fragrance, have an alpha, beta-unsaturated carbonyl unit or mesomeric limiting forms thereof.
- Preferred perfume ketones are in particular selected from buccoxime, iso-jasmone, methylnaphthyl ketone, muskindanone, tonalide / musk plus, alpha-damascone, beta-damascone, delta-damascone, gamma-damascone, damascenone, damarose, methyldihydrojasmonate, menthone, car - ionone called, camphor, fenchone, ionone alpha, beta-ionone, gamma-methyl, Fleuramon, di- hydrojasmon, cis-jasmone, iso-e-Super ®, Methylcedrenylketon or methyl cedrylone, acetophenone, methylacetophenone, p-methoxyacetophenone, Methyl-beta-naphthyl ketone, benzylacetone, benzo
- the ketones may be selected from the Damascans, carvone, gamma-methyl-ionone, iso-E-super, 2,4,4,7-tetramethyl-oct-6-en-3-one, benzylacetone, damascenone, methyl dihydrojasmonate, methylcedrylon, hedione, and mixtures thereof. Most preferred are all damascone and damascenone. By exposure to light comprising the wavelengths of 200 to 400 nm, the stored ketones can be released.
- Preferred perfume esters are selected from cinnamic acid esters and derivatives of cinnamic acid esters.
- Particularly preferred Linaloylcinnamat, 3-Phenylpropylcinnamat, Eugenolcinnamat, allyl are cinnamate, benzyl cinnamate, butyl cinnamate, ethyl cinnamate, methyl cinnamate, Menthylcinnamat, Hep tylcinnamat, Cylclohexylcinnamat, Isoamylcinnamat, Isobutylcinnamat, Isopentylcinnamat, isopropyl pylcinnamat, Isoheptylcinnamat, Tetrahydrofurfurylcinnamat and cinnamyl cinnamate.
- the stored esters can be released.
- the substituent R 2 in the formula (I) is a linear or branched, substituted or unsubstituted alkyl group having 1 to 6 C atoms, preferably 1 to 3 C atoms, in particular a methyl radical.
- a compound of the general formula (I) according to the invention is preferred in which four of the five aryl substituents R3, R4, R5, R6 and R7 are hydrogen.
- At least one of the substituents R4 and R5 are each a quaternary ammonium radical of the formula (II). Substitution in the para position (R5) is particularly preferred because the electronic structure of the aromatic ring can be most effectively modified here whereby the absorption maximum of compounds of general formula (I) can be easily adapted to a particular wavelength.
- the substituents R3, R4, R6 and R7 are therefore each hydrogen and the radical R5 is a quaternary ammonium radical of the formula (II),
- R 8, R 9 and R 10 is a methyl group. If only one of the radicals R 8, R 9 or R 10 is a methyl group, then it is particularly preferred if the other two radicals are joined together by ring closure. When two of R8, R9 and R10 are methyl, it is particularly preferred that the third is an alkyl chain of 12 to 20 carbon atoms.
- compounds of the formula (I) correspond to the following formulas (III), (IV), (V), (VI), (VII), (VIII), (IX) and (X):
- the compounds according to the invention in particular the compounds of the formulas (III) to (XIV) can be stably incorporated into the customary washing or cleaning agent matrices, into cosmetics and existing perfume compositions.
- Compounds of formulas (III) to (X) enable sustained release of the stored perfume ketones, such as Damascone in the alpha, beta, gamma or delta form and of damascenone, in particular beta-damascenone.
- Compounds of formulas (XI) to (XIV) allow sustained release of the stored perfume esters.
- ketones and esters give usual washing or cleaning agents as well as cosmetics a particularly long lasting freshness impression.
- the dried, washed textile benefits from the good long-term freshness effect.
- Another object of the present invention is a washing or cleaning agent, preferably a detergent, fabric softener or washing aid, comprising at least one compound according to one of the formulas (I) and / or (III) to (XIV), wherein said compound is preferably in amounts between 0.0001 and 5 wt .-%, advantageously between 0.001 and 4 wt .-%, more preferably between 0.01 and 3 wt .-%, in particular between 0, 1 and 2% by weight, respectively based on the total mean, is included.
- Suitable cleaning agents are, for example, cleaners for hard surfaces, such as preferably dishwashing detergents. It may also be detergents such as household cleaners, all-purpose cleaners, window cleaners, floor cleaners, etc.
- it can be a product for cleaning toilet bowls and urinals, advantageously a rinsing cleaner for hanging in the toilet bowl, in particular a so-called toilet block.
- the washing or cleaning agent according to the invention comprises at least one surfactant selected from anionic, cationic, nonionic, zwitterionic, amphoteric surfactants or mixtures thereof.
- the agent according to the invention is in solid or liquid form.
- a further subject of the invention is a cosmetic agent comprising at least one compound according to one of the formulas (I) and / or (III) to (XIV) which preferably contains said compound in amounts between 0.0001 and 5% by weight, advantageously between 0.001 and 4 wt .-%, more preferably between 0.01 and 3 wt .-%, in particular between 0, 1 and 2% by weight, each based on the total agent contains.
- Another object of the invention is a Kunststoffbeduftungssch (eg, air freshener, room deodorant, room spray, etc.) containing at least one compound according to one of the formulas (I) and / or (III) to (XIV), said compound preferably in amounts between 0 , 0001 and 50 wt .-%, advantageously between 0.001 and 5 wt .-%, more preferably between 0.1 and 3 wt .-%, in particular between 0.1 and 2 wt .-%, each based on the total agent , is included.
- a Kunststoffbeduftungssch eg, air freshener, room deodorant, room spray, etc.
- an agent according to the invention ie washing or cleaning agent, cosmetic or room fragrancing agent
- additional fragrances in particular selected from the group comprising fragrances of natural or synthetic origin, preferably more volatile fragrances, higher-boiling fragrances, solid Fragrances and / or adherent fragrances.
- Adhesion-resistant fragrances which are advantageously usable in the context of the present invention are, for example, essential oils such as angelica root oil, aniseed oil, arnica blossom oil, basil oil, bay oil, bergamot oil, Champacabell oil, Edeltannenöl, Edeltannenzapfen oil, Elemiöl, Eucalyptusöl, Fen- chel, pine, galbanum, geranium, ginger, guaiac, ginger, broom, oil Caraway Oil, Cumin Oil, Lavender Oil, Lemongrass Oil, Lime Oil, Mandarin Oil, Melissa Oil, Musk Grain Oil, Myrrh Oil, Clove Oil, Neroli Oil, Niaouli Oil, Olibanum Oil, Orange Oil, Origanum Oil, Palmarosa Oil, Patchouli Oil, Peru Balsam Oil, Petitgrain Oil, Pepper Oil, Peppermint Oil, Pimento Oil, Pine Oil, Rose Oil, Rosemary oil, sandalwood oil, celery oil, spiked oil, star aniseed oil, tur
- fragrances can be used in the context of the present invention as adherent fragrances or perfume mixtures, ie fragrances.
- These compounds include the following compounds and mixtures thereof: ambrettolide, alpha-amylcinnamaldehyde, anethole, anisaldehyde, anisalcohol, anisole, methyl anthranilate, acetophenone, benzylacetone, benzaldehyde, ethyl benzoate, benzophenone, benzyl alcohol, benzyl acetate, benzyl benzoate, benzyl formate, benzyl valerate , Borneol, bornyl acetate, alpha-bromostyrene, n-decyl aldehyde, n-dodecyl aldehyde, eugenol, eugenol methyl ether, eucalyptol, far
- the more volatile fragrances include in particular the lower-boiling fragrances of natural or synthetic origin, which can be used alone or in mixtures.
- Examples of more volatile fragrances are alkyl isothiocyanates (alkylmustard oils), butanedione, limonene, linalool, linayl acetate and propionate, menthol, menthone, methyl-n-heptenone, phellandrene, phenylacetaldehyde, terpinyl acetate, citral, citronellal.
- the agent according to the invention i.e.
- washing or cleaning agent, cosmetic agent, or room scenting agent at least one, preferably several, active components, in particular washing, care, cleaning active and / or cosmetic components, advantageously selected from the group consisting of anionic surfactants, cationic surfactants, amphoteric surfactants, nonionic surfactants, alkalizing agents, anti-crease compounds, antibacterial agents, antioxidants, anti-redeposition agents, antistatic agents, builders, bleaching agents, Bleach activators, bleach stabilizers, bleach catalysts, ironing assistants, cobuilders, fragrances, anti-shrinkage agents, electrolytes, enzymes, colorants, colorants, dyes, color transfer inhibitors, fungicides, germicides, odoriferous substances, adjuvants, hydrotropes, rinse aids, complexing agents, preservatives, corrosion inhibitors, water-miscible organic solvents , optical brighteners, perfume carriers, pearlescers, pH adjusters, repellents and impregnating agents, polymers, swelling and anti-s
- the amounts of the individual ingredients in the agents according to the invention i. Detergents or cleaners, cosmetics or room fragrancing agents are each based on
- the surfactant content will be higher or lower.
- the surfactant content of, for example, detergents may be between 10 and 50% by weight, preferably between 12.5 and 30% by weight, and more preferably between 15 and 25% by weight, while e.g. Detergent for automatic dishwashing e.g. between 0.1 and 10 wt .-%, preferably between 0.5 and 7.5 wt .-% and in particular between 1 and 5 wt .-% surfactants may contain.
- compositions according to the invention may contain surfactants, preference being given to anionic surfactants, nonionic surfactants and mixtures thereof, but also cationic surfactants.
- Suitable nonionic surfactants are in particular ethoxylation and / or propoxylation of alkyl glycosides and / or linear or branched alcohols each having 12 to 18 carbon atoms in the alkyl moiety and 3 to 20, preferably 4 to 10 alkyl ether groups.
- ethoxylation and / or propoxylation products of N-alkylamines, vicinal diols, fatty acid esters and fatty acid amides which correspond to said long-chain alcohol derivatives with respect to the alkyl moiety and of alkylphenols having 5 to 12 C atoms in the alkyl radical.
- Suitable anionic surfactants are in particular soaps and those which contain sulfate or sulfonate groups with preferably alkali ions as cations.
- Useful soaps are preferred Alkali salts of saturated or unsaturated fatty acids having 12 to 18 carbon atoms. Such fatty acids can also be used in incompletely neutralized form.
- Useful surfactants of the sulfate type include the salts of the sulfuric acid half-esters of fatty alcohols having 12 to 18 carbon atoms and the sulfation products of said nonionic surfactants having a low degree of ethoxylation.
- Suitable surfactants of the sulfonate type include linear alkylbenzenesulfonates having 9 to 14 carbon atoms in the alkyl moiety, alkanesulfonates having 12 to 18 carbon atoms, and olefin sulfonates having 12 to 18 carbon atoms, in the reaction of corresponding monoolefins with sulfur trioxide and alpha-sulfofatty acid esters formed in the sulfonation of fatty acid methyl or ethyl esters.
- Cationic surfactants are preferably selected from esterquats and / or quaternary ammonium compounds (QAV) according to the general formula (R I ) (R ") (R"') (R IV ) N + X - , in which R 1 to R IV for identical or different Ci_ 2 2-alkyl radicals, C 7 .
- QAV quaternary ammonium compounds
- X represents halide ions, sulfate ions, hydroxide ions or similar anions.
- QACs can be prepared by reaction of tertiary amines with alkylating agents, such as, for example, methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide.
- alkylating agents such as, for example, methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide.
- alkylation of tertiary amines with a long alkyl radical and two methyl groups is particularly easy Quaternization of tertiary amines with two long radicals and one methyl group can also be carried out under mild conditions with the aid of methyl chloride.
- Amines having three long alkyl radicals or hydroxy-substituted alkyl radicals are less reactive quaternized with, for example, dimethyl sulfate.
- zalkonium chloride N-alkyl-N, N-dimethylbenzylammonium chloride
- benzalkone B m, p-dichlorobenzyldimethyl-C 12 -alkylammonium chloride
- benzoxonium chloride benzyl-dodecyl-bis- (2-hydroxyethyl) -ammonium chloride), cetrimonium bromide (N- Hexadecyl-N, N-trimethylammoniumbromide
- benzetononium chloride N, N-dimethyl-N [2- [2- [2- [p- (1,1,3,3-tetramethylbutyl) phenoxy] ethoxy] ethyl] benzylammonium chloride
- Preferred ester quats are methyl N- (2-hydroxyethyl) -N, N-di (tallowacyl oxyethyl) ammonium methosulfate, bis (palmitoyl) ethyl hydroxyethyl methyl ammonium methosulfate or methyl N, N bis (acyloxyethyl) -N- (2-hydroxyethyl) ammonium methosulfate.
- Methylhydroxyalkyldialkoylo- xyalkylammoniummethosulfate sold by the company Stepan under the trademark Stepantex ® or known under the trade name Dehyquart ® products of BASF SE or known under the name Rewoquat ® products of the manufacturer Evonik Industries AG.
- Surfactants are present in the compositions according to the invention (ie detergents or cleaners, cosmetic compositions or room fragrancing agents) in proportions of preferably from 5% by weight to 50% by weight, in particular from 8% by weight to 30% by weight , Particularly in laundering agents, preferably up to 30% by weight, in particular from 5% by weight to 15% by weight, of surfactants, among these preferably at least partially cationic surfactants, are used.
- An agent according to the invention in particular washing or cleaning agent, preferably contains at least one water-soluble and / or water-insoluble, organic and / or inorganic builder.
- the water-soluble organic builder substances include polycarboxylic acids, in particular citric acid and sugar acids, monomeric and polymeric aminopolycarboxylic acids, in particular methylglycinediacetic acid, nitrilotriacetic acid and ethylenediaminetetraacetic acid and polyaspartic acid, polyphosphonic acids, in particular aminotris (methylenephosphonic acid), ethylenediaminetetrakis (methylenephosphonic acid) and 1-hydroxyethane-1,1-diphosphonic acid, polymeric hydroxy compounds such as dextrin and also polymeric (poly) carboxylic acids, polymeric acrylic acids, methacrylic acids, maleic acids and mixed polymers thereof, which may also contain polymerized small amounts of polymerizable substances without carboxylic acid functionality.
- Suitable, albeit less preferred, compounds of this class are copolymers of acrylic acid or methacrylic acid with vinyl ethers, such as vinylmethyl ethers, vinyl esters, ethylene, propylene and styrene, in which the proportion of the acid is at least 50% by weight. All of the acids mentioned are generally used in the form of their water-soluble salts, in particular their alkali metal salts.
- organic builder substances may be present in amounts of up to 40% by weight, in particular up to 25% by weight and preferably from 1% by weight to 8% by weight. Quantities close to the stated upper limit are preferably used in paste-form or liquid, in particular water-containing, agents according to the invention. Aftertreatment agents according to the invention, such as e.g. Softener, may optionally also be free of organic builder.
- Suitable water-soluble inorganic builder materials are, in particular, alkali metal silicates and polyphosphates, preferably sodium triphosphate, for example zeolite A, P or X.
- inorganic builder substances are preferably present in the agents according to the invention in amounts of up to 60% by weight, in particular from 5% by weight to 40% by weight.
- Aftertreatment agents according to the invention such as e.g. Softener, are preferably free of inorganic builder.
- Suitable peroxygen compounds are in particular organic peracids or peracid salts of organic acids, such as phthalimidopercaproic acid, perbenzoic acid or salts of diperdodecanedioic acid, hydrogen peroxide and, under the conditions of use, hydrogen peroxide-releasing inorganic salts, such as perborate, percarbonate and / or persilicate.
- organic peracids or peracid salts of organic acids such as phthalimidopercaproic acid, perbenzoic acid or salts of diperdodecanedioic acid, hydrogen peroxide and, under the conditions of use, hydrogen peroxide-releasing inorganic salts, such as perborate, percarbonate and / or persilicate.
- bleach stabilizers such as phosphonates, borates or metaborates and metasilicates and magnesium salts such as magnesium sulfate may be useful.
- Suitable enzymes which can be used in the compositions are those from the class of proteases, cutinases, amylases, pullulanases, hemicellulases, cellulases, lipases, oxidases and peroxidases and mixtures thereof. Particularly suitable are from fungi or bacteria, such as Bacillus subtilis, Bacillus licheniformis, Streptomyces griseus, Humicola lanuginosa, Humicola insolens, Pseudomonas pseudoalcaligenes or Pseudomonas cepacia derived enzymatic agents.
- the optionally used enzymes may be adsorbed to carriers and / or embedded in encapsulants to protect against premature inactivation. If desired, they are preferably present in the compositions according to the invention in amounts of not more than 5% by weight, in particular from 0.2% by weight to 2% by weight.
- the teaching according to the invention can be used to significantly reduce the perfume fraction in detergents or cleansers and cosmetic products. This makes it possible to offer perfumed products even for those particularly sensitive consumers who can not use normally perfumed products due to special intolerances and irritations, or only to a limited extent.
- a preferred solid, in particular powdered, detergent according to the invention may in particular also contain components which are e.g. are selected from the following:
- Anionic surfactants preferably alkylbenzenesulfonate, alkylsulfate, e.g. in amounts of preferably 5-30% by weight
- Nonionic surfactants such as preferably fatty alcohol polyglycol ethers, alkylpolyglucoside, fatty acid glucamide, e.g. in amounts of preferably 0.5-15% by weight
- Builders e.g. Zeolite, polycarboxylate, sodium citrate, in amounts of e.g. 0-70% by weight, advantageously 5-60% by weight, preferably 10-55% by weight, in particular 15-40% by weight,
- Alkalis for example sodium carbonate, in amounts of, for example, 0-35% by weight, advantageously 1-30% by weight, preferably 2-25% by weight, in particular 5-20% by weight
- Bleaching agents for example sodium perborate, sodium percarbonate, in amounts of, for example, 0-30% by weight, advantageously 5-25% by weight, preferably 10-20% by weight
- - corrosion inhibitors e.g. Sodium silicate
- amounts of e.g. 0-10% by weight advantageously 1-6% by weight, preferably 2-5% by weight, in particular 3-4% by weight,
- Stabilizers e.g. Phosphonates, advantageously 0-1% by weight
- Foam inhibitor e.g. Soap, silicone oils, paraffins, advantageously 0-4% by weight, preferably 0.1-3% by weight, in particular 0.2-1% by weight,
- Enzymes e.g. Proteases, amylases, cellulases, lipases, advantageously 0-2% by weight, preferably 0.2-1% by weight, in particular 0.3-0.8% by weight,
- - grayness inhibitor e.g. Carboxymethylcellulose, advantageously 0-1% by weight
- Discoloration inhibitor e.g. Polyvinylpyrrolidone derivatives, preferably 0-2% by weight,
- Optical brighteners e.g. Stilbene derivatives, biphenyl derivatives, advantageously 0-0.4% by weight, in particular 0.1-1.3% by weight,
- the agent is in liquid form, preferably in gel form.
- Preferred liquid detergents or cleaners contain water as the main solvent and optionally non-aqueous solvents.
- a preferred liquid, in particular gel detergent according to the invention may contain, in particular, components which are e.g. are selected from the following:
- Anionic surfactants preferably alkylbenzenesulfonate, alkylsulfate, e.g. in amounts of preferably 5-40% by weight
- Nonionic surfactants such as preferably fatty alcohol polyglycol ethers, alkylpolyglucoside, fatty acid glucamide, e.g. in amounts of preferably 0.5-25% by weight
- Builders e.g. Polycarboxylate, sodium citrate, advantageously 0-15% by weight, preferably 0.01-10% by weight, in particular 0.1-5% by weight,
- Foam inhibitor e.g. Soap, silicone oils, paraffins, in amounts of e.g. 0-10% by weight, advantageously 0, 1-4% by weight, preferably 0.2-2% by weight, in particular 1-3% by weight,
- Enzymes for example proteases, amylases, cellulases, lipases, in amounts of, for example, 0-3 wt .-%, advantageously 0.1-2 wt .-%, preferably 0.2-1 wt .-%, in particular 0.3 -0.8% by weight
- Optical brighteners eg stilbene derivative, biphenyl derivative, in amounts of, for example, 0-1% by weight, advantageously 0.1-0.3% by weight, in particular 0-1-0.4% by weight .
- optionally soap in quantities of e.g. 0-25% by weight, advantageously 1-20% by weight, preferably 2-15% by weight, in particular 5-10% by weight,
- solvents preferably alcohols
- solvents advantageously 0-25 wt .-%, preferably 1- 20 wt .-%, in particular 2-15 wt .-%, wt .-% in each case based on the total agent.
- a preferred liquid fabric softener according to the invention may in particular also contain components which are selected from the following:
- Cationic surfactants such as in particular esterquats, e.g. in amounts of 2-30% by weight, cosurfactants, e.g. Glycerol monostearate, stearic acid, fatty alcohols, fatty alcohol ethoxylates, e.g. in amounts of 0-5% by weight, preferably 0.1-4% by weight,
- Emulsifiers e.g. Fatty amine ethoxylates, e.g. in amounts of 0-4 wt .-%, preferably
- Stabilizers preferably in the ppm range
- Solvents e.g. Water, in amounts of preferably 60-90% by weight,
- a further subject of the invention is a process for the long-lasting scenting of surfaces, where a compound according to one of the formulas (I) and / or (III) to (XIV) or a detergent or cleaning agent according to the invention is applied to the surface to be scented (US Pat. For example, textile, dishes, floor) is applied and said surface is then exposed to electromagnetic radiation comprising the wavelengths of 200 to 400 nm.
- Another object of the invention is a method for long-lasting room fragrance, wherein an inventive Jardinbeduftungssch of electromagnetic radiation comprising the wavelengths of 200 to 400 nm is exposed.
- step 2 In a round bottom flask, the product formed in step 2 and an excess of N-methylpyrrolidine in toluene are introduced, stirred at 60 ° C for 16 h and worked up after cooling.
- reaction solution is then stirred at -78 ° C for 30 minutes. Subsequently, 14.8 g of delta-Damascone are slowly added dropwise by means of a dropping funnel and the reaction solution was stirred at -78 ° C on. Thereafter, the cooling is removed and at a temperature of about -10 ° C, the addition of a saturated ammonium chloride solution. For purification, it is extracted 3 times with 350 ml of ether each time, and the resulting pale yellow organic phase is then extracted by shaking with water, later with saturated NaCl solution. The organic phase is then dried over magnesium sulfate. The filtrate is freed from solvent under reduced pressure. The resulting crude product is finally distilled under high vacuum. The desired target product results in an amount of 29 g.
- the compound prepared in this way showed a very good odor effect when used in detergents and fabric softeners in textile treatment.
- a better durability of the fragrance impression was found on the laundry washed and then dried, compared with detergents and fabric softeners which contained an equivalent amount of delta-damascone, but otherwise were the same.
- the fresh fragrance impression of the textiles lasted much longer, both after drying the linen and especially after drying in the machine dryer.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102012210566A DE102012210566A1 (de) | 2012-06-22 | 2012-06-22 | Photolabile Duftspeicherstoffe |
PCT/EP2013/058683 WO2013189647A1 (de) | 2012-06-22 | 2013-04-26 | Photolabile duftspeicherstoffe |
Publications (1)
Publication Number | Publication Date |
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EP2864287A1 true EP2864287A1 (de) | 2015-04-29 |
Family
ID=48326276
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP13721307.0A Withdrawn EP2864287A1 (de) | 2012-06-22 | 2013-04-26 | Photolabile duftspeicherstoffe |
Country Status (4)
Country | Link |
---|---|
US (2) | US9284261B2 (de) |
EP (1) | EP2864287A1 (de) |
DE (1) | DE102012210566A1 (de) |
WO (1) | WO2013189647A1 (de) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102015220929A1 (de) * | 2015-10-27 | 2017-04-27 | Henkel Ag & Co. Kgaa | Photolabile Duftspeicherstoffe |
FR3091877B1 (fr) | 2019-01-22 | 2023-06-16 | Calyxia | Compositions de detergence avec des propriétés olfactives améliorées |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE60136178D1 (de) * | 2000-06-15 | 2008-11-27 | Firmenich & Cie | Verwendung von ketonen als vorstufen von aktiven verbindungen |
DE102006003092A1 (de) | 2006-01-20 | 2007-07-26 | Henkel Kgaa | 1-Aza-3,7-dioxabicyclo[3.3.0]octan-Verbindungen und ihre Verwendung als Pro-Fragrances |
DE102010002006A1 (de) | 2010-02-17 | 2011-08-18 | Henkel AG & Co. KGaA, 40589 | Photolabile Duftspeicherstoffe |
-
2012
- 2012-06-22 DE DE102012210566A patent/DE102012210566A1/de not_active Withdrawn
-
2013
- 2013-04-26 WO PCT/EP2013/058683 patent/WO2013189647A1/de unknown
- 2013-04-26 EP EP13721307.0A patent/EP2864287A1/de not_active Withdrawn
-
2014
- 2014-12-15 US US14/570,053 patent/US9284261B2/en not_active Expired - Fee Related
-
2016
- 2016-02-01 US US15/012,227 patent/US9730875B2/en not_active Expired - Fee Related
Non-Patent Citations (2)
Title |
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None * |
See also references of WO2013189647A1 * |
Also Published As
Publication number | Publication date |
---|---|
US20160143829A1 (en) | 2016-05-26 |
US9284261B2 (en) | 2016-03-15 |
US9730875B2 (en) | 2017-08-15 |
WO2013189647A1 (de) | 2013-12-27 |
DE102012210566A1 (de) | 2013-12-24 |
US20150099810A1 (en) | 2015-04-09 |
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