EP1268382A2 - Alcools de substances odorantes alcoxyles et leur utilisation - Google Patents

Alcools de substances odorantes alcoxyles et leur utilisation

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Publication number
EP1268382A2
EP1268382A2 EP01933723A EP01933723A EP1268382A2 EP 1268382 A2 EP1268382 A2 EP 1268382A2 EP 01933723 A EP01933723 A EP 01933723A EP 01933723 A EP01933723 A EP 01933723A EP 1268382 A2 EP1268382 A2 EP 1268382A2
Authority
EP
European Patent Office
Prior art keywords
fragrance
alkoxylated
alcohols
preparation
general formula
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.)
Withdrawn
Application number
EP01933723A
Other languages
German (de)
English (en)
Inventor
Thomas Otto Gassenmeier
Lars Zander
Wolfgang Von Rybinski
Ute Krupp
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE10013766A external-priority patent/DE10013766A1/de
Priority claimed from DE10013764A external-priority patent/DE10013764A1/de
Priority claimed from DE10013762A external-priority patent/DE10013762A1/de
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1268382A2 publication Critical patent/EP1268382A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/10—Saturated ethers of polyhydroxy compounds
    • C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the present invention relates to alkoxylated fragrance alcohols.
  • the present invention relates to fragrance alcohols, especially terpene alcohols, with a defined number of eth ⁇ xy and / or pr ⁇ poxy groups in the molecule.
  • the present invention further relates to the production of alkoxylated fragrance alcohols, in particular alkoxylated terpene alcohols, and their use in washing, rinsing, cleaning or conditioning agents or cosmetic preparations.
  • Terpenes and their osmophore-bearing derivatives play a central role among the fragrances, i.e. those regularly volatile substances that trigger a pleasant sense of smell in humans.
  • Terpene alcohols in particular play an important role as fragrances: They were previously obtained from plant sources and are part of many essential oils, but are now also accessible synthetically.
  • Fragrance alcohol esters and especially terpene alcohol esters with inorganic acids or (optionally lower alkoxylated) carboxylic acids, namely fragrance alcohol-atherpene alcohol sulfonates, sulfates, phosphates etc. as precursors for fragrances in cosmetic preparations are described in WO 97/30687 (Givaudan -Roure International SA).
  • the publication describes that the esters are odorless at room temperature and normal pressure, but under suitable conditions, for example on the Body surface when used as a deodorant, split and release the alcohols, which then show their organoleptic properties.
  • Fragrances have long been used in detergents, dishwashing detergents, cleaners or cosmetics as well as in cosmetic preparations.
  • they serve less - as in earlier times - to mask unpleasant smells of the components contained in the above-mentioned agents or preparations, but are primarily used to treat both the products themselves and the objects or agents treated with the agents
  • product identification is also achieved by the consumer via the fragrance of the product or the fragrance transmitted by the product to the object being treated; the advertising of the fragrance ("April freshness";"lemonscent”) makes use of this product identification and is used to promote sales.
  • fragrance note is given a special place in advertising, and thus also in consumer presentation, especially for avivage products.
  • manufacturers of detergents, dishwashing detergents, cleaning agents, and cosmetics as well as the manufacturers of cosmetic preparations Need for a way to fix fragrances on treated objects on the one hand and thus only to enable fragrances to be released after the treatment, but on the other hand also to extend the time for the release of the fragrances after the treatment.
  • controlled release The controlled release of fragrances in a wide variety of preparations in the washing, rinsing, cleaning and personal care sector, often referred to as "controlled release", is the subject of numerous publications and patent applications. This reflects the fact that the release of fragrances is of outstanding importance in this technical field, because - for the reasons mentioned above - both the product and the washing, rinsing, cleaning or finishing agent solution and those using these agents treated objects should be scented intensively and long-lasting.
  • fragrances In addition to the methods of applying fragrances to carrier materials and coating the scented carriers or encapsulating or encapsulating fragrances or storing them in compounds (for example cyclodextrin-perfume complexes), there is the possibility of chemically binding the fragrances to carrier media, the chemical bond slowly being broken down and the fragrance is released.
  • This principle has been implemented, for example, in the esterification of fragrance alcohols - as already mentioned above - a broad state of the art exists for this group of substances in addition to the publication WO 97/30687: for example, it is proposed to bind fragrant alcohols to non-volatile siloxanes which they are slowly released by hydrolysis.
  • the siloxane esters Under normal manufacturing conditions of densified particle mixtures such as granulation or press agglomeration, the siloxane esters also tend to release the fragrance alcohol already during manufacture, ie prematurely. There is therefore a need to provide fragrance forms which scent both the product and the washing, cleaning or aviva solution or the cosmetic preparation, the fragrance on the objects treated, in particular on textiles, being intended to last as long as possible.
  • alkoxylated fragrance alcohols in particular alkoxylated terpene alcohols, achieve the above objects. This is all the more surprising since ethers - and these include alkoxylated fragrance alcohols and alkoxylated terpene alcohols - have a comparatively high stability to hydrolysis in an aqueous environment.
  • the alkoxylated fragrance alcohols or terpene alcohols according to the invention are notable for good adhesive strength.
  • the alkoxylated terpene alcohols are excellent as fragrance boosters.
  • a fragrance booster is to be understood as a substance that is able to give the olfactory impressions of the components of a multi-substance system, i.e. a mixture of two or more fragrances to intensify sustainably.
  • the invention therefore relates to alkoxylated fragrance alcohols of the general formula (I)
  • R 1 represents the scent alkyl radical of a scented alcohol of the formula R 1 OH;
  • R 2 and R 2 ' independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2' being hydrogen;
  • - n stands for an integer from 1 to 100.
  • the present invention relates to alkoxylated fragrance alcohols of the general formula (I)
  • R 1 represents the scent alkyl radical of a scented alcohol of the formula R 1 OH;
  • R 2 and R 2 ' independently of one another are hydrogen or a CH radical, at least one of the radicals R 2 and R 2' being hydrogen;
  • - n stands for an integer from 1 to 100
  • the invention also relates to a process for the preparation of the above-mentioned alkoxylated fragrance alcohols of the general formula (I) by reacting a fragrance alcohol of the general formula
  • R 1 has the meaning given above, with one or more alkylene oxide (s) of the general formula
  • R 2 and R 2 have the meanings given above, in the molar ratio of fragrance alcohol: alkylene oxide in the range from 1: 1 to 1: 100 in the presence of an alkoxylation catalyst at a temperature in the range from room temperature to 200 ° C. and a pressure in the range from normal pressure to 10 Mpa, especially 1 Mpa, in the presence or absence of a solvent for a time until all of the alkylene oxide has been taken up, for example for a time in the range from 0.1 to 5 h, deactivating the catalyst and optionally isolating the product.
  • the invention also relates to the use of alkoxylated scented alcohols of the general formula (I) in washing, rinsing, cleaning and finishing agents or in cosmetic preparations.
  • the present invention thus comprises alkoxylated fragrance alcohols of the general formula (I)
  • the radical R 1 is selected from the group of fragrance alcohol residues R 1 of fragrance alcohols R 1 OH.
  • fragrance alcohols is understood to mean fragrance molecules which have free hydroxyl groups which can be etherified, regardless of how the molecule is further structured.
  • Salicylic acid ethers are also conceivable as fragrance alcohol alkoxylates.
  • fragrance alcohols Preferred representatives can be named from the large group of fragrance alcohols, so that alkoxylated fragrance alcohols of the general formula (I) in which R 1 is selected from the group of the following fragrance alcohol residues: 10-undecene-1 are preferred in the context of the present invention -yl, 2,5-dimethylhept-2-yl, 2,6-dimethylhept-2-yl, 2-methylbutyl, 2-methylpentyl, 2-phenoxyethyl, 2-phenylpropyl, 2-tert-butylcyclohexyl, 3.5 , 5-Trimethylcyclohexyl, 3-Hexyl, 3-Methyl-5-phenylpentyl, 3-Oct- yl, 3-phenylpropyl, 4-heptenyl, 4-isopropylcyclohexyl, 4-tert-butylcyclohexyl, 6,8-dimethyl-2-nonyl, 6-nonen-1-yl, 9-dec
  • the radical R 1 in the general formula (I) is an isononyl radical.
  • alkoxylated isononyl alcohols of the general formula (I) show outstanding properties in connection with the desired properties as long-lasting fragrances.
  • the radical R 1 in the general formula (I) represents a terpene radical of a terpene alcohol R 1 OH.
  • Particularly preferred according to the invention are alkoxylated terpene alcohols of the above general formula (I), in which R 1 is selected from the group geranyl, citronellyl, tetrahydrogeranyl, linaloyl, dihydrolinaloyl, tetrahydrolinaloyl, neryl, myrcenyl, dihydromyrcenyl, lavendulyl, farnesyl, isolidophenylulentyl, menthyl Terpinyl, tetrahydromuguyl, thymyl, 2,5-dimethylhept-2-yl and phenylethyl.
  • R 3 in the general formula (I) is particularly preferably hydrogen.
  • the alkoxylated fragrance alcohols according to the invention, in particular the alkoxylated terpene alcohols are therefore particularly preferably the non-derivatized direct reaction products of an alkoxylation of the corresponding fragrance or terpene alcohols.
  • R 2 and of R 2 ' independently of one another can be hydrogen or methyl (CH 3 ), at least one of the radicals R 2 and R 2' being hydrogen.
  • the alkoxylated fragrance alcohols or terpene alcohols are thus ethoxylates or propoxylates or alkoxylated derivatives of the corresponding fragrance alcohols or terpene alcohols which contain both ethoxy groups and propoxy groups.
  • the number of alkoxy groups in the molecule - indicated by the index n - can vary within wide ranges and is, according to the invention, in the range from 1 to 100, preferably in the range from 3 to 50, more preferably in the range from 5 to 30 and most preferably in the range from 5 to 20.
  • general formula (I) includes both alkoxylated fragrance alcohols in which ethoxy groups and propoxy groups are randomly arranged in the alkoxy chain (“random polymers”), as well as those alkoxylated fragrance alcohols in which blocks of several ethoxy groups in addition to blocks of several propoxy groups in the Chain are arranged ("block copolymers”).
  • the latter alkoxylated fragrance alcohols, preferably alkoxylated terpene alcohols can also be represented by the following general formula (Ia), which is a special case of the general formula (I):
  • R 1 , R 2 , R 2 and R 3 have the same meaning as in the general formula (I), k is an integer from 1 to 99, m is an integer from 1 to 99 and the sum of k and m represents an integer from 2 to 100.
  • the above formula (Ia) is to be understood such that a scent alkoxy radical / terpene alkoxy radical R 1 O- is attached to an ethoxy block as well can also be bound to a propoxy block and the block bound to R 1 O is then followed in each case by a block of the other type. Of course, a block of the other type can then be connected again, if necessary, even if this does not result directly from the general formula (Ia).
  • the stipulations for the total number of blocks of the respective type as well as the total number of all blocks are the above-mentioned ranges of the numbers for k and m and their sum, which is in any case at or above 2 and should not exceed 100.
  • a particularly preferred embodiment of the invention corresponds to alkoxylated fragrance alcohols, in particular alkoxylated terpene alcohols, of the general formula (I) and of the general formula (Ia)
  • R 1 represents the scent alkyl radical of a scented alcohol of the formula R 1 OH;
  • R 2 and R 2 ' independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2' being hydrogen;
  • - n is an integer from 1 to 100;
  • k is an integer from 1 to 99
  • m is an integer from 1 to 99 and the sum of k and m is an integer from 2 to 100;
  • scented alcohol alkoxylates are particularly preferred according to the invention in which 3, 6, 7, 10 or 20 alkoxy radicals are bonded to a scented alkoxy radical or terpene alkoxy radical and the number of ethoxy groups present statistically in a large amount of the product Residues or propoxy residues in the abovementioned cases vary, for example, only between 1 and 5 or between 4 and 8 or between 4 and 9 or between 7 and 13 or between 17 and 23. Products with a narrow distribution of the number of alkoxy groups result in particularly good properties in terms of fragrance adhesion and release.
  • fragrance alcohol alkoxylates which can be used advantageously according to the invention on account of the good fragrance properties are the compounds represented by the following formulas (1.1.) To (I.8.):
  • R 2 and R 2 ' independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2' being hydrogen; and n represents an integer ranging from 5 to 20.
  • the present invention also extends to a process for the preparation of alkoxylated fragrance alcohols of the general formula (I)
  • R 1 represents the scent alkyl radical of a scented alcohol of the formula R 1 OH;
  • R 2 and R 2 independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2 being hydrogen;
  • - n stands for an integer from 1 to 100.
  • the method comprises reacting a fragrance alcohol of the general formula
  • R 1 has the meaning given above, with one or more alkylene oxide (s) of the general formula
  • the starting material for the first process step are fragrance alcohols or terpene alcohols of the general formula R 1 OH.
  • R 1 can have all those meanings which have already been mentioned above in connection with the introduction of the new alkoxylated fragrance alcohols or alkoxylated terpene alcohols.
  • fragrance alcohols or terpene alcohols from the group isononanol, geraniol, citronellol, tetrahydrogeraniol, tetra- hydrolinalool, nerol, myrcenol, dihydromyrcenol, Lavendulol, farnesol, neroli dol, menthol, isopulegol, terpineol, thymol, phenylethanol, tetrahydromuguol and Dimetol® R (2,5-dimethylheptan-2-ol), more preferably isononanol, geraniol, terpineol, thymol, farnesol, citronellol, tetrahydromuguol, 2,5-dimethylheptan-2-ol and phenylethanol.
  • an alcohol can occur in several isomers (for example farnesol, nerolid
  • the scented alcohol R 1 OH is combined with one or more alkylene oxides of the formula
  • R 2 - CH ⁇ - CH - R 2 wherein R 2 and R 2 'have the meanings given above, that is to say can be H or CH 3 , where at least one of the radicals R 2 and R 2 is H.
  • a reaction with only one alkylene oxide leads to alkoxylated fragrance alcohols or terpene alcohols with only one type from the group - [CH (R 2 ) -CH (R 2 ' ) -Oj n -, ie to fragrance alcohol ethoxides or fragrance alcohol propoxides, while the simultaneous reaction with ethylene oxide and propylene oxide leads to alkoxylation products in which ethylene oxide groups and propylene oxide groups are randomly distributed in the molecule (“random alkoxylates”), and the successive reaction with the two alkylene oxides to give alkoxylation products with successive blocks of ethylene oxide (EO) or propylene oxide (PO) leads, for example those as represented by the following formula (la)
  • R 1 , R 2 , R 2 ' and R 3 have the meanings defined above, k is an integer from 1 to 99, m is an integer from 1 to 99 and the sum of k and m is an integer Number from 2 to 100 stands.
  • the molar ratio of fragrance alcohol to alkylene oxide (s) largely depends on the desired alkoxylation number of the fragrance alcohol or terpene alcohol and is preferably in the range from 1: 1 to 1: 100, even more preferably in the range of 1: 1 to 1:50.
  • An alkoxylation catalyst is used for the alkoxylation reaction, which can be carried out in the presence or absence of a solvent.
  • An alkaline alkoxylation catalyst has proven particularly useful, preferably an alkali metal hydroxide. If a so-called “narrow-rank alkoxylation" catalyst is used, preferably a catalyst from the group of calcined talcites, the reaction leads to alkali oxylated fragrance alcohols or alkoxylated terpene alcohols with the particularly preferred narrow distribution of the number of ethoxy and / or propoxy groups.
  • the alkoxylation reaction is carried out at a temperature in the range from room temperature to 200 ° C., preferably in the range from 50 to 170 ° C., and at a pressure in the range from normal pressure to 10 MPa, preferably in the range from 0.1 to 1 MPa long until the alkylene oxide has been completely taken up, preferably over a time in the range from 0.1 to 5 hours.
  • the catalyst used is destroyed. This is done in a manner known per se to the person skilled in the art, for example by acidifying the reaction mixture to the neutral point.
  • the product obtained can then be used for the desired purpose without any problems or, if appropriate, in a manner known per se, for example by distillation under controlled conditions, of starting materials which have not reacted, or of products whose degree of alkoxylation is not in the range desired for the product lies, separated and so isolated.
  • the invention also includes the use of alkoxylated fragrance alcohols, in particular alkoxylated terpene alcohols, of the general formula (I)
  • R 1 represents the scent alkyl radical of a scented alcohol of the formula R 1 OH;
  • - R 2 and R 2 independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2 being hydrogen;
  • - n stands for an integer from 1 to 100
  • alkoxylated fragrance alcohols in particular alkoxylated terpene alcohols according to the present invention are used in the respective compositions or preparations.
  • the fragrance is intensified and lasts for a long time.
  • R 2 and R 2 ' independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2' being hydrogen; and and n stands for an integer in the range from 5 to 20, preferably in which n varies by at most ⁇ 3, preferably by at most ⁇ 2, by a certain numerical value.
  • the invention therefore furthermore relates to a preparation comprising, in addition to customary constituents of a detergent preparation, dishwashing liquid preparation, detergent preparation, finishing preparation or cosmetic preparation, one or more alkoxylated fragrance alcohols of the general formula (I)
  • R 1 represents the scent alkyl radical of a scented alcohol of the formula R 1 OH;
  • R 2 and R 2 ' independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2 being hydrogen;
  • - n stands for an integer from 1 to 100.
  • the invention also relates to a method for modifying the fragrance impression of one or more fragrance (s) contained in a multi-substance mixture by adding an amount of one or more alkoxylated fragrance alcohols of the general formula (I) which modifies the fragrance impression
  • R 1 represents the scent alkyl radical of a scented alcohol of the formula R 1 OH;
  • R 2 and R 2 ' independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2 being hydrogen;
  • the invention also relates to washing processes, rinsing processes, cleaning processes or finishing processes, in which preparations, in particular preparations containing surfactants, according to the invention are put into the respective - often aqueous
  • the invention also relates to a cosmetic treatment method in which a cosmetic preparation, in particular a surfactant-containing cosmetic preparation, according to the invention is brought into contact with the human body or a part thereof and is treated cosmetically in this way.
  • surfactant-containing preparations in the broadest sense include preparations in solid form (particles, powder, etc.), semi-solid form (pastes, etc.), liquid form (solutions, emulsions, suspensions, gels, etc.) and gas-like form ( Aerosols etc.) which contain one or more surfactants with a view to an advantageous action, usually in addition to other components which are customary for the particular application.
  • surfactant-free preparations can also be used according to the invention, their importance - for example in of cosmetics
  • surfactant-containing preparations which, however, are not intended to limit the invention but only to explain it, are surfactant-containing detergent preparations, surfactant-containing detergent preparations, surfactant-containing detergent preparations or surfactant-containing finishing agents (which can each be solid or liquid, but can also be present in one form , which comprises solid and liquid components or subsets of the components next to one another), as well as surfactant-containing cosmetic preparations; the latter can also be solid or liquid or in a form are present, which comprises solid and liquid components or subsets of the components side by side.
  • washing, rinsing, cleaning and finishing agent preparations comprise as active substances substances such as surfactants (anionic, non-ionic, cationic and amphoteric surfactants), builder substances (inorganic and organic builder substances), bleaching agents (such as, for example, peroxo bleaching agents and chlorine bleaching agents).
  • active substances such as surfactants (anionic, non-ionic, cationic and amphoteric surfactants), builder substances (inorganic and organic builder substances), bleaching agents (such as, for example, peroxo bleaching agents and chlorine bleaching agents).
  • bleaching agents such as, for example, peroxo bleaching agents and chlorine bleaching agents.
  • the preparations according to the invention which may contain surfactants, comprise detergents in addition to the usual constituents of a detergent preparation, detergents in addition to the usual constituents of a detergent preparation, detergents in addition to the usual constituents of a detergent preparation, finishing agents in addition to the usual constituents of a detergent preparation and cosmetic agents in addition to the usual constituents of a cosmetic preparation (the usual constituents of the preparations mentioned are explained in more detail below) one or more alkoxylated fragrance alcohols of the general formula (I)
  • R 1 represents the scent alkyl radical of a scented alcohol of the formula R 1 OH;
  • R 2 and R 2 independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2 being hydrogen;
  • - n stands for an integer from 1 to 100.
  • the surfactant-containing preparations according to the present invention thus comprise a single or else a mixture of two or more alkoxylated fragrance alcohols of the above-mentioned general formula (I).
  • the preparations according to the invention in particular the surfactant-containing preparations, contain alkoxylated fragrance alcohols, in particular alkoxylated terpene alcohols, of the general formula (I) and of the general formula (Ia)
  • R 1 represents the scent alkyl radical of a scented alcohol of the formula R 1 OH;
  • R 2 and R 2 independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2 being hydrogen;
  • - n is an integer from 1 to 100;
  • k is an integer from 1 to 99
  • m is an integer from 1 to 99 and the sum of k and m is an integer from 2 to 100; with narrow distribution of the number of ethoxy and / or propoxy groups.
  • compositions according to the invention with alkoxylated fragrance alcohols which can be used advantageously due to the good fragrance properties are surfactant-containing preparations with the compounds represented by the following formulas (1.1.) To (I.8.):
  • R 2 and R 2 ' independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2 being hydrogen; and n represents an integer ranging from 5 to 20.
  • the surfactant-containing preparations according to the invention contain one or more alkoxylated scented alcohols of the general formula (I) in an amount of 0.001 to 10% by weight, preferably in an amount of 01 to 5 wt .-%, particularly preferably in an amount of 0.02 to 3 wt .-% and in particular in an amount of 0.05 to 2 wt .-%, based on the surfactant-containing washing, rinsing, cleaning - or finishing agent preparation.
  • the surfactant-containing preparations according to the invention contain one or more substances from the group of surfactants, surfactant compounds, builders, bleaching agents, bleach activators, enzymes, foam inhibitors, dyes and - in the event that the surfactant-containing preparations are at least partly as moldings available - binding and disintegration aids.
  • surfactants surfactant compounds
  • builders bleaching agents
  • bleach activators enzymes
  • foam inhibitors dyes and - in the event that the surfactant-containing preparations are at least partly as moldings available - binding and disintegration aids.
  • the surfactant-containing preparations according to the invention can contain surface-active substances from the group of anionic, nonionic, zwitterionic or cationic surfactants, anionic surfactants being clearly preferred for economic reasons and on the basis of their performance spectrum.
  • anionic surfactants of the sulfonate and sulfate type are used.
  • Suitable surfactants of the sulfonate type are preferably Cg.-13 alkyl benzene sulfonates, olefin sulfonates, ie mixtures of alkene and hydroxyalkanesulfonates and also disulfonates, as obtained, for example, from C 12-i 8 monoolefins with an internal or terminal double bond by Sulfonation with gaseous sulfur trioxide and subsequent alkaline or acid hydrolysis of the sulfonation products is obtained.
  • alkanesulfonates obtained from C 2-18 alkanes, for example by sulfochlorination or sulfoxidation with subsequent hydrolysis or neutralization.
  • the esters of 2-sulfofatty acids for example the 2-sulfonated methyl esters of hydrogenated coconut, palm kernel or tallow fatty acids, are also suitable.
  • Suitable anionic surfactants are sulfated fatty acid glycerol esters.
  • Fatty acid glycerol esters are to be understood as the mono-, di- and triesters as well as their mixtures as they are produced by esterification of a mono- glycerol with 1 to 3 moles of fatty acid or in the transesterification of triglycerides with 0.3 to 2 moles of glycerol can be obtained.
  • Preferred sulfated fatty acid glycerol esters are the sulfonation products of saturated fatty acids having 6 to 22 carbon atoms, for example caproic acid, caprylic acid, capric acid, myristic acid, lauric acid, palmitic acid, stearic acid or behenic acid.
  • alk (en) yl sulfates are the alkali and in particular the sodium salts of the sulfuric acid semiesters of the C 2 -C 8 fatty alcohols, for example from coconut fatty alcohol, tallow fatty alcohol, lauryl, myristyl, cetyl or stearyl alcohol or the C 1 -C 2 o-oxo alcohols and those half-esters of secondary alcohols of this chain length are preferred.
  • alk (en) yl sulfates of the chain length mentioned which contain a synthetic, straight-chain alkyl radical prepared on a petrochemical basis and which have a degradation behavior analogous to that of the adequate compounds based on oleochemical raw materials.
  • Ci 2 -C 6 alkyl sulfates and C ⁇ -C ⁇ alkyl sulfates and C 4 -C 15 alkyl sulfates are preferred for washing technology reasons.
  • 2,3-alkyl sulfates which are produced for example in accordance with US Patent No. 3,234,258 or 5,075,041 and can be obtained as commercial products from Shell Oil Company under the name DAN ®, are suitable anionic surfactants.
  • the Schwefelklasted Acidmonoester of linear or branched C ethoxylated with 1 to 6 mol ethylene oxide 7 - 2 i-alcohols such as 2-methyl-branched Cg-n-alcohols containing on average 3.5 mol ethylene oxide (EO) or C ⁇ 2 -i 8 -Fatty alcohols with 1 to 4 EO are suitable. Because of their high foaming behavior, they are used in cleaning agents only in relatively small amounts, for example in amounts of 1 to 5% by weight.
  • Suitable anionic surfactants are also the salts of alkylsulfosuccinic acid, which are also known as sulfosuccinates or as sulfosuccinic acid esters, and the monoesters and / or diesters of sulfosuccinic acid with alcohols, preferably fatty alcohols and especially ethoxylated fatty acids. represent alcohols.
  • Preferred sulfosuccinates contain C ⁇ -i ⁇ fatty alcohol residues or mixtures thereof.
  • Particularly preferred sulfosuccinates contain a fatty alcohol residue which is derived from ethoxylated fatty alcohols, which in themselves are nonionic surfactants (description see below).
  • alk (en) ylsuccinic acid with preferably 8 to 18 carbon atoms in the alk (en) yl chain or salts thereof.
  • Soaps are particularly suitable as further anionic surfactants.
  • Saturated fatty acid soaps are suitable, such as the salts of lauric acid, myristic acid, palmitic acid, stearic acid, hydrogenated erucic acid and behenic acid, and in particular from natural fatty acids, e.g. Coconut, palm kernel or tallow fatty acids, derived soap mixtures.
  • the anionic surfactants can be in the form of their sodium, potassium or ammonium salts and also as soluble salts of organic bases, such as mono-, di- or triethanolamine.
  • the anionic surfactants are preferably in the form of their sodium or potassium salts, in particular in the form of the sodium salts.
  • surfactants are used in the form of their magnesium salts.
  • surfactant-containing preparations which each contain 5 to 50% by weight, preferably 7.5 to 40% by weight and in particular 15 to 25% by weight, of one or more anionic surfactant (s) based on the surfactant-containing preparation.
  • Preferred surfactant Preparations according to the invention have a soap content which exceeds 0.2% by weight, based on the total weight of the surfactant-containing preparation.
  • the preferred anionic surfactants are the alkylbenzenesulfonates and fatty alcohol sulfates, preferred surfactant-containing preparations being 2 to 20% by weight, preferably 2.5 to 15% by weight and in particular 5 to 10% by weight of fatty alcohol sulfate (s), each based on the weight of the present surfactant-containing preparation according to the invention
  • the nonionic surfactants used are preferably alkoxylated, advantageously ethoxylated, in particular primary alcohols having preferably 8 to 18 carbon atoms and an average of 1 to 12 moles of ethylene oxide (EO) per mole of alcohol, in which the alcohol radical can be linear or preferably methyl-branched in the 2-position or may contain linear and methyl-branched radicals in the mixture, as are usually present in oxo alcohol radicals.
  • EO ethylene oxide
  • alcohol ethoxylates with linear residues of alcohols of native origin with 12 to 18 carbon atoms, for example from coconut, palm, tallow or oleyl alcohol, and an average of 2 to 8 EO per mole of alcohol are particularly preferred.
  • the preferred ethoxylated alcohols include, for example, -C 2 alcohols with 3 EO or 4 EO, C 9-11 alcohol with 7 EO, C 3 - 5 alcohols with 3 EO, 5 EO, 7 EO or 8 EO, C ⁇ 2 -i 8 alcohols with 3 EO, 5 EO or 7 EO and mixtures of these, and mixtures of C ⁇ 2- ⁇ 4 alcohol with 3 EO and C ⁇ 2-18 alcohol with 5 EO.
  • the degrees of ethoxylation given represent statistical averages, which can be an integer or a fraction for a specific product.
  • Preferred alcohol ethoxylates have a narrow homolog distribution (narrow range ethoxylates, NRE).
  • fatty alcohols with more than 12 EO can also be used. Examples of this are tallow fatty alcohol with 14 EO, 25 EO, 30 EO or 40 EO.
  • nonionic surfactants that are used either as the sole nonionic surfactant or in combination with other nonionic surfactants are alkoxylated, preferably ethoxy lated or ethoxylated and propoxylated fatty acid alkyl esters, preferably having 1 to 4 carbon atoms in the alkyl chain, in particular fatty acid methyl esters, as described, for example, in Japanese patent application JP 58/217598 or preferably according to that described in international patent application WO-A-90/13533 Process are made.
  • alkyl polyglycosides Another class of nonionic surfactants that can be used advantageously are the alkyl polyglycosides (APG).
  • Alkypolyglycosides that can be used satisfy the general formula RO (G) z , in which R represents a linear or branched, in particular methyl-branched, saturated or unsaturated, aliphatic radical having 8 to 22, preferably 12 to 18, C atoms and G is Is symbol which stands for a glycose unit with 5 or 6 carbon atoms, preferably for glucose.
  • the degree of glycosidation z is between 1.0 and 4.0, preferably between 1.0 and 2.0 and in particular between 1.1 and 1.4.
  • Linear alkyl polyglucosides ie alkyl polyglycosides, in which the polyglycosyl radical is a glucose radical and the alkyl radical is an n-alkyl radical are preferably used.
  • the surfactant-containing preparations according to the invention can preferably contain alkyl polyglycosides, with APG contents of more than 0.2% by weight, based on the preparation as a whole, being preferred for washing, rinsing or cleaning purposes.
  • Particularly preferred surfactant-containing preparations contain APG in amounts of 0.2 to 10% by weight, preferably in amounts of 0.2 to 5% by weight and in particular in amounts of 0.5 to 3% by weight.
  • Nonionic surfactants of the amine oxide type for example N-coconut alkyl-N, N-dimethylamine oxide and N-tallow alkyl-N, N-dihydroxyethylamine oxide, and the fatty acid alkanolamides can also be suitable.
  • the amount of this non- Ionic surfactants are preferably not more than that of the ethoxylated fatty alcohols, in particular not more than half of them.
  • surfactants are polyhydroxy fatty acid amides of the formula (II),
  • RCO stands for an aliphatic acyl radical with 6 to 22 carbon atoms
  • R ⁇ for hydrogen, an alkyl or hydroxyalkyl radical with 1 to 4 carbon atoms
  • [Z] for a linear or branched polyhydroxyalkyl radical with 3 to 10 carbon atoms and 3 to 10 hydroxyl groups.
  • the polyhydroxy fatty acid amides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
  • the group of polyhydroxy fatty acid amides also includes compounds of the formula (III)
  • R represents a linear or branched alkyl or alkenyl radical having 7 to 12 carbon atoms
  • R 5 represents a linear, branched or cyclic alkyl radical or an aryl radical having 2 to 8 carbon atoms
  • R 6 represents a linear, branched or cyclic alkyl radical or an aryl radical or an oxy- Alkyl radical having 1 to 8 carbon atoms
  • [Z] stands for a linear polyhydroxyalkyl radical, the alkyl chain of which is substituted with at least two hydroxyl groups, or alkoxylated, preferably ethoxylated or propylated, derivatives of this radical.
  • [Z] is preferably obtained by reductive amination of a reduced sugar, for example glucose, fructose, maltose, lactose, galactose, mannose or xylose.
  • a reduced sugar for example glucose, fructose, maltose, lactose, galactose, mannose or xylose.
  • the N-alkoxy- or N-aryloxy-substituted compounds can then be converted, for example according to the teaching of international application WO-A-95/07331, by reaction with fatty acid methyl esters in the presence of an alkoxide as catalyst into the desired polyhydroxy fatty acid amides.
  • cationic surfactants in addition to anionic and nonionic surfactants. They are preferably used as washing performance boosters, whereby only small amounts of cationic surfactants are required. If cationic surfactants are used, they are preferably present in the preparations in amounts of from 0.01 to 10% by weight, in particular from 0.1 to 3.0% by weight.
  • the surfactant-containing preparations according to the invention are detergents
  • the amount of surfactant is not the same in all portions; rather, partial portions with a relatively larger and partial portions with a relatively smaller surfactant content can be provided.
  • the surfactant-containing preparations according to the invention are cleaning agents, in particular dishwashing agents
  • They usually contain one or more surfactant (s) in total amounts of 0.1 to 10% by weight, preferably in amounts of 0.5 to 5% by weight
  • surfactants in larger or smaller amounts in partial portions of the preparations according to the invention could be.
  • the amount of surfactant is not the same in all portions, even with detergents or dishwashing detergents; rather, partial portions with a relatively larger and partial portions with a relatively smaller surfactant content can be provided.
  • the surfactant-containing preparations according to the invention can usually contain builders used in washing and cleaning agents, in particular thus zeolites, silicates, carbonates, organic cobuilders and - where there are no ecological prejudices against their use - the phosphates.
  • Suitable crystalline, layered sodium silicates have the general formula NaMSi x O 2 + ⁇ 'H 2 O, where M is sodium or hydrogen, x is a number from 1, 9 to 4 and y is a number from 0 to 20 and preferred values for x 2, 3 or 4.
  • M sodium or hydrogen
  • x is a number from 1, 9 to 4
  • y is a number from 0 to 20 and preferred values for x 2, 3 or 4.
  • Such crystalline layered silicates are described, for example, in European patent application EP-A-0 164 514.
  • Preferred crystalline layered silicates of the formula given are those in which M represents sodium and x assumes the values 2 or 3.
  • both ⁇ - and ⁇ -sodium disilicate Na 2 Si 2 O 5 - yH 2 O are preferred, with ⁇ -sodium disilicate being able to be obtained, for example, by the process described in international patent application WO-A-91/08171.
  • the dissolution delay compared to conventional amorphous sodium silicates can be done in different ways, for example by surface treatment, compounding, compacting / compression or caused by overdrying.
  • the term “amorphous” is also understood to mean “X-ray amorphous”.
  • silicates in X-ray diffraction experiments do not provide sharp X-ray reflections, as are typical for crystalline substances, but at most one or more maxima of the scattered X-rays, which have a width of several degree units of the diffraction angle.
  • it can very well lead to particularly good builder properties if the silicate particles deliver washed-out or even sharp diffraction maxima in electron diffraction experiments. This is to be interpreted as meaning that the products have microcrystalline areas of size 10 to a few hundred nm, values up to max. 50 nm and in particular up to max. 20 nm are preferred.
  • Such so-called X-ray amorphous silicates which also have a delay in dissolution compared to conventional water glasses, are described, for example, in German patent application DE-A-44 00 024. Compacted / compacted amorphous silicates, compounded amorphous silicates and over-dried X-ray amorphous silicates are particularly preferred.
  • An optionally used finely crystalline, synthetic and bound water-containing zeolite is preferably zeolite A and / or P.
  • Zeolite P-type is particularly preferred as zeolite MAP (e.g. commercial product: Doucil A24 from Crosfield).
  • zeolite X and mixtures of A, X and / or P are also suitable.
  • Commercially available and can preferably be used in the context of the present invention for example a co-crystallizate of zeolite X and zeolite A (about 80% by weight of zeolite X) ), which is sold by CONDEA Augusta SpA under the brand name VEGOBOND AX ® and by the formula
  • Suitable zeolites have an average particle size of less than 10 ⁇ m (volume distribution; measurement method: Coulter Counter) and preferably contain 18 to 22% by weight, in particular 20 to 22% by weight, of bound water.
  • phosphates as builders in detergents, provided that such use should not be avoided for ecological reasons.
  • the sodium salts of orthophosphates, pyrophosphates and in particular tripolyphosphates are particularly suitable.
  • Usable organic builders are, for example, the polycarboxylic acids which can be used in the form of their sodium salts, polycarboxylic acids being understood to mean those carboxylic acids which carry more than one acid function.
  • these are citric acid, adipic acid, succinic acid, glutaric acid, malic acid, tartaric acid, maleic acid, fumaric acid, sugar acids, aminocarboxylic acids, nitrilotriacetic acid (NTA), as long as their use is not objectionable for ecological reasons, and mixtures of these.
  • Preferred salts are the salts of polycarboxylic acids such as citric acid, adipic acid, succinic acid, glutaric acid, tartaric acid, sugar acids and mixtures of these.
  • the acids themselves can also be used.
  • the acids typically also have the property of an acidifying component and thus also serve to establish a lower and milder pH of surfactant-containing preparations according to the invention.
  • citric acid, succinic acid, glutaric acid, adipic acid, gluconic acid and any mixtures of these should be mentioned in particular.
  • Polymeric polycarboxylates are also suitable as builders. These are, for example, the alkali metal salts of polyacrylic acid or polymethacrylic acid, for example those with a molecular weight of 500 to 70,000 g / mol.
  • the molar masses given for polymeric polycarboxylates are weight-average molar masses M w of the particular acid form, which were determined in principle by means of gel permeation chromatography (GPC), a UV detector being used.
  • GPC gel permeation chromatography
  • the measurement was made against an external polyacrylic acid standard, which provides realistic molecular weight values due to its structural relationship to the polymers investigated. This information differs significantly from the molecular weight information for which polystyrene sulfonic acids are used as standard.
  • the molecular weights measured against polystyrene acids are generally significantly higher than the molecular weights specified in the context of the present invention.
  • Suitable polymers are, in particular, polyacrylates, which preferably have a molecular weight of 2,000 to 20,000 g / mol. Because of their superior solubility, the short-chain polyacrylates with molecular weights of 2,000 to 10,000 g / mol, particularly preferably 3,000 to 5,000 g / mol, can in turn be preferred from this group.
  • copolymeric polycarboxylates in particular those of acrylic acid with methacrylic acid or of acrylic acid or methacrylic acid with maleic acid.
  • Copolymers of acrylic acid with maleic acid which contain 50 to 90% by weight of acrylic acid and 50 to 10% by weight of maleic acid have proven to be particularly suitable.
  • Their relative molar mass, based on free acids, is generally 2,000 to 70,000 g / mol, preferably 20,000 to 50,000 g / mol and in particular 30,000 to 40,000 g / mol.
  • the (co) polymeric polycarboxylates can be used either as a powder or as an aqueous solution.
  • the content of the surfactant-containing The preparation of (co) polymeric polycarboxylates is preferably 0.5 to 20% by weight, in particular 3 to 10% by weight.
  • the polymers can also contain allylsulfonic acids, such as, for example, in EP-B 0 727 448, allyloxybenzenesulfonic acid and methallylsulfonic acid as a monomer.
  • allylsulfonic acids such as, for example, in EP-B 0 727 448, allyloxybenzenesulfonic acid and methallylsulfonic acid as a monomer.
  • biodegradable polymers composed of more than two different monomer units, for example those which, according to DE-A 43 00 772, are salts of acrylic acid and maleic acid as well as vinyl alcohol or vinyl alcohol derivatives or according to DE-C 42 21 381 contain as monomers salts of acrylic acid and 2-alkylallylsulfonic acid and sugar derivatives.
  • copolymers are those described in German patent applications DE-A 43 03 320 and DE-A 44 17 734 and preferably contain acrolein and acrylic acid / acrylic acid salts or acrolein and vinyl acetate as monomers.
  • polymeric aminodicarboxylic acids their salts or their precursor substances.
  • Particularly preferred are polyaspartic acids or their salts and derivatives, of which it is disclosed in German patent application DE-A 195 40 086 that, in addition to co-builder properties, they also have a bleach-stabilizing effect.
  • polyacetals which can be obtained by reacting dialdehydes with polyolcarboxylic acids which have 5 to 7 carbon atoms and at least 3 hydroxyl groups, for example as described in European patent application EP-A 0 280 223.
  • Preferred polyacetals are derived from dialdehydes such as glyoxal, Glutaraldehyde, te Rephthalaldehyde and mixtures thereof and from polyol carboxylic acids such as gluconic acid and / or glucoheptonic acid.
  • Suitable organic builder substances are dextrins, for example oligomers or polymers of carbohydrates, which can be obtained by partial hydrolysis of starches.
  • the hydrolysis can be carried out by customary processes, for example acid-catalyzed or enzyme-catalyzed. They are preferably hydrolysis products with average molecular weights in the range from 400 to 500,000 g / mol.
  • DE dextrose equivalent
  • oxidized derivatives of such dextrins are their reaction products with oxidizing agents which are capable of oxidizing at least one alcohol function of the saccharide ring to the carboxylic acid function.
  • oxidizing agents capable of oxidizing at least one alcohol function of the saccharide ring to the carboxylic acid function.
  • Such oxidized dextrins and processes for their preparation are known in particular from European patent applications EP-A 0 232 202, EP-A 0 427 349, EP-A 0 472 042 and EP-A 0 542 496 and from international patent applications WO 92/18542 , WO 93/08251, WO 93/16110, WO 94/28030, WO 95/07303, WO 95/12619 and WO 95/20608.
  • Oxydisuccinates and other derivatives of disuccinates are further suitable co-builders.
  • Ethylene diamine N, N'-disuccinate (EDDS) the synthesis of which is described, for example, in US Pat. No. 3,158,615, is preferably used in the form of its sodium or magnesium salts.
  • glycerol disuccinates and glycerol trisuccinates are also preferred.
  • organic co-builders are, for example, acetylated hydroxycarboxylic acids or their salts, which may also be present in lactone form and which contain at least 4 carbon atoms and at least one hydroxyl group and a maximum of two acid groups.
  • Such co-builders are described, for example, in international patent application WO 95/20029.
  • phosphonates are in particular hydroxyalkane or aminoalkanephosphonates.
  • Preferred aminoalkane phosphonates are ethylenediaminetetramethylenephosphonate (EDTMP), diethylenetriaminepentamethylenephosphonate (DTPMP) and their higher homologs.
  • EDTMP hexasodium salt of EDTMP or as the hepta- and octasodium salt of DTPMP.
  • HEDP is preferably used as the builder from the class of the phosphonates.
  • the aminoal Kanphosphonates also have a strong ability to bind heavy metals. Accordingly, in particular if the surfactant-containing preparations according to the invention also contain bleach, it may be preferred to use aminoalkane phosphonates, in particular DTPMP, or to use mixtures of the phosphonates mentioned.
  • the surfactant-containing preparations according to the invention can, in particular as detergents or cleaning agents, include other ingredients from the group of bleaching agents, bleach activators, enzymes, fragrances, perfume carriers, fluorescent agents, dyes, foam inhibitors, silicone oils, antireflective detergents or detergents. contain deposition agents, optical brighteners, graying inhibitors, color transfer inhibitors and corrosion inhibitors.
  • bleaching agents which can be used are, for example, sodium percarbonate, peroxypyrophosphates, citrate perhydrates and H 2 O 2 -producing peracidic salts or peracids, such as perbenzoates, peroxophthalates, diperazelaic acid, phthaloiminoperacid or diperdodecanedioic acid. If cleaning or bleaching preparations for machine dishwashing are produced, bleaching agents from the group of organic bleaching agents can also be used. Typical organic bleaching agents are the diacyl peroxides, such as dibenzoyl peroxide.
  • organic bleaching agents are peroxy acids, examples of which include alkyl peroxy acids and aryl peroxy acids.
  • Preferred representatives are (a) peroxybenzoic acid and its ring-substituted derivatives, such as alkylperoxybenzoic acids, but also peroxy- ⁇ -naphthoic acid and magnesium monoper phthalate; (b) the aliphatic or substituted aliphatic peroxy acids, such as peroxylauric acid, peroxystearic acid, ⁇ -phthalimidoperoxy-caproic acid [phthaloiminoperoxyhexanoic acid (PAP)], o-carboxybenzamido-per-oxycaproic acid, N-nonenylamido operadipic acid and N-succinate; and (c) aliphatic and araliphatic peroxydicarboxylic acids, such as 1, 12-diperoxycarboxylic acid, 1, 9-diperoxyazelaic acid, diperocysebacic acid
  • Chlorine or bromine-releasing substances can also be used as bleaching agents in compositions for machine dishwashing.
  • Suitable chlorine or bromine-releasing materials include, for example, heterocyclic N-bromo- and N-chloramides, for example trichloroisocyanuric acid, tribromoisocyanuric acid, dibromoisocyanuric acid and / or dichloroisocyanuric acid (DICA) and / or their salts with cations such as potassium and sodium.
  • Hydantoin compounds such as 1,3-dichloro-5,5-dimethylhydantoin are also suitable.
  • bleach activators can be incorporated into the surfactant-containing preparations.
  • Bleach activators which can be used are compounds which, under perhydrolysis conditions, give aliphatic peroxocarboxylic acids having preferably 1 to 10 C atoms, in particular 2 to 4 C atoms, and / or optionally substituted perbenzoic acid.
  • Suitable substances are those which carry O- and / or N-acyl groups of the number of carbon atoms mentioned and / or optionally substituted benzoyl groups.
  • TAED tetra
  • bleach catalysts can also be incorporated into the surfactant-containing preparations.
  • These substances are bleach-enhancing transition metal salts or transition metal complexes such as, for example, Mn, Fe, Co, Ru or Mo salt complexes or carbonyl complexes.
  • Mn, Fe, Co, Ru, Mo, Ti, V and Cu complexes with N-containing tripod ligands as well as Co, Fe, Cu and Ru amine complexes can also be used as bleaching catalysts.
  • Suitable enzymes are those from the class of proteases, lipases, amylases, cellulases or mixtures thereof. Enzymes obtained from bacterial strains or fungi such as Bacillus subtilis, Bacillus licheniformis and Streptomyces griseus are particularly suitable. Proteases of the subtilisin type and in particular proteases which are obtained from Bacillus lentus are preferably used.
  • Enzyme mixtures for example of protease and amylase or protease and lipase or proteases and cellulase or of cellulase and lipase or of protease, amylase and lipase or protease, lipase and cellulase, but in particular mixtures containing cellulase, are of particular interest.
  • Peroxidases or oxidases have also proven to be suitable in some cases.
  • the enzymes can be adsorbed on carriers and / or embedded in coating substances in order to protect them against premature decomposition.
  • the proportion of enzymes, enzyme mixtures or enzyme granules in the surfactant-containing preparations according to the invention can be, for example, about 0.1 to 5% by weight, preferably 0.1 to about 2% by weight.
  • the surfactant-containing preparations according to the invention also contain further additives as are known from the prior art as additives for detergent or cleaning agent preparations. These can either be added to one or more portions of the surfactant-containing preparations according to the invention or, if necessary, to all partial portions (detergent-active preparations) or - as described in the copending patent application No. 199 29 098.9 entitled "Active ingredient portion pack" - in water-soluble, the materials comprising detergent formulations, for example in water-soluble films, but also in capsules or coatings which can be used according to the invention, are incorporated.
  • optical brighteners customary in detergents can be used here. These are added as an aqueous solution or as a solution in an organic solvent to the polymer solution which is converted into the film, or are added to a portion (detergent-active preparation) of a detergent or cleaning agent in solid or liquid form.
  • optical brighteners are derivatives of diaminostilbenedisulfonic acid or its alkali metal salts. Are suitable for. B.
  • salts of 4, 4'-bis (2-anilino-4-morpholinol, 3,5-triazinyl-6-amino-) stilbene-2,2'-disulfonic acid or compounds of similar structure which instead of the morpholino group a Diethanolamino group, a methylamino group, an anilino group or a 2-methoxyethylamino group.
  • brighteners of the type of the substituted diphenylstyryl can be contained in the partial portions (detergent preparations) of the surfactant-containing preparations according to the invention, e.g. B.
  • UV protection substances are substances which are released in the washing liquor during the washing process or during the subsequent fabric softening process and which accumulate on the fiber in order to then achieve a UV protection effect. Products from Ciba Specialty Chemicals that are commercially available under the name Tinosorb are suitable.
  • dyes are preferred according to the invention.
  • Dyes are preferred here, as are usually used to improve the optical product appearance in washing, rinsing, cleaning and finishing agents.
  • the choice of such dyes does not pose any difficulties for the person skilled in the art, in particular since such customary dyes have a high storage stability and insensitivity to the other ingredients of the detergent preparations and to light, and have no pronounced substance towards textile fibers, in order not to dye them.
  • the dyes are present in the surfactant-containing preparations according to the invention in amounts of less than 0.01% by weight.
  • Another class of additives that can be added to the surfactant-containing preparations according to the invention are polymers.
  • these polymers are, on the one hand, polymers which show cobuilder properties during washing or cleaning or rinsing, for example polyacrylic acids, also modified polyacrylic acids or corresponding copolymers.
  • Another group of polymers are polyvinylpyrrolidone and other graying inhibitors, such as copolymers of polyvinylpyrrolidone, cellulose ether and the like.
  • so-called soil repellents as are known to the person skilled in the detergent and cleaning agent and are described in detail below, are also suitable as polymers.
  • Another group of additives are bleaching catalysts, in particular bleaching catalysts for automatic dishwashing detergents or detergents. Complexes of manganese and cobalt are used here, especially with nitrogen-containing ligands.
  • silver protection agents are a large number of mostly cyclic organic compounds which are likewise familiar to the person skilled in the art and which help to prevent tarnishing of silver-containing objects during the cleaning process.
  • Specific examples can be triazoles, benzotriazoles and their complexes with metals such as Mn, Co, Zn, Fe, Mo, W or Cu.
  • the surfactant-containing preparations can also contain so-called soil repellents, that is to say polymers which build up on fibers or hard surfaces (for example on porcelain and glass), have a positive influence on the oil and fat washability from textiles and thus counteract any soiling in a targeted manner , This effect is particularly evident when a textile or a hard object (porcelain, glass) is soiled that has already been washed several times beforehand with a washing or cleaning agent according to the invention which contains this oil and fat-dissolving component.
  • soil repellents that is to say polymers which build up on fibers or hard surfaces (for example on porcelain and glass)
  • the preferred oil and fat-dissolving components include, for example, nonionic cellulose ethers such as methyl cellulose and methyl hydroxypropyl cellulose with a proportion of methoxy groups of 15 to 30% by weight and of hydroxypropoxy groups of 1 to 15% by weight, based in each case the nonionic cellulose ether, and the polymers of phthalic acid and / or terephthalic acid or their derivatives known from the prior art, in particular polymers of ethylene terephthalates and / or polyethylene glycol terephthalates or anionically and / or nonionically modified derivatives thereof. Of these, the sulfonated derivatives of phthalic acid and terephthalic acid polymers are particularly preferred.
  • All of these additives are added to the surfactant-containing preparations according to the invention in amounts of at most 30% by weight, preferably 2 to 20% by weight.
  • the addition can also be made to a material of a water-soluble enclosure, which comprises one or more of the washing-active preparations.
  • detergent and cleaning agent ingredients which can occur in the surfactant-containing preparations according to the invention, provided they are detergents, dishwashing detergents or cleaning agents, is by no means exhaustive, but merely reflects the essential typical ingredients of such agents.
  • organic solvents can also be contained in the agents. It is preferably monohydric or polyhydric alcohols having 1 to 4 carbon atoms. Preferred alcohols in such agents are ethanol, 1, 2-propanediol, glycerol and mixtures of these alcohols. In preferred embodiments, such agents contain 2 to 12% by weight of such alcohols.
  • Preparations according to the invention can also be cosmetic preparations which differ in their composition from washing, rinsing, cleaning and finishing agents as described above. In particular, this applies to non-surfactant-containing cosmetic preparations according to the present invention.
  • the invention also includes surfactant-containing cosmetic preparations.
  • These cosmetic compositions preferably contain alkoxylated fragrance alcohols of the formula (I) in an amount of 0.001 to 10% by weight, preferably in an amount of 0.01 to 5% by weight, particularly preferably preferably in an amount of 0.02 to 3 and in particular in an amount of 0.05 to 2% by weight, in each case based on the cosmetic agent.
  • the cosmetic agents are aqueous preparations which may contain surfactants or surface-active substances and which are particularly suitable for the treatment of keratin fibers, in particular human hair, or for the treatment of human skin.
  • Fatty alcohol polyglycol ether sulfates are predominantly used for the most important group of ingredients, the surface-active (surfactant) active ingredients or detergent active ingredients, in some cases in combination with other, usually anionic, surfactants.
  • surfactants should be compatible with the skin and mucous membranes. According to the legal regulations, there should be good biodegradability.
  • preferred agents may additionally contain further surfactants, such as alkyl sulfates, alkyl ether carboxylates, preferably with degrees of ethoxylation of 4 to 10, and surfactant protein-fatty acid condensates.
  • surfactants such as alkyl sulfates, alkyl ether carboxylates, preferably with degrees of ethoxylation of 4 to 10, and surfactant protein-fatty acid condensates.
  • the protein-abietic acid condensate deserves special mention here.
  • Sulfosuccinic acid esters, amidopropyplbetaines, amphoacetates and amphodiacetates are also preferred surfactants used in hair shampoos.
  • auxiliaries Another group of ingredients is summarized under the term auxiliaries and is very diverse: For example, additions of non-ionic surfactants such as ethoxylated sorbitan esters or protein hydrolysates increase the tolerance or have an irritant effect, eg. B. in baby shampoos; serve as moisturizers to prevent excessive degreasing when washing hair, e.g. B. natural oils or synthetic fatty acid esters; Glycerin, sorbitol, propylene glycol (see propanediols), polyethylene glycols and other polyols serve as humectants. To improve wet combability and reduction of electrostatic charge on the hair after drying can shampoo the cationic surfactants such. B.
  • Quaternary ammonium compounds can be added. Dyes or pearlescent pigments are added for a colored, brilliant appearance. Thickeners of different substance classes can be used to adjust the desired viscosity. B. achieved on the basis of citrate, lactate or phosphate. In order to ensure sufficient durability and shelf life, preservatives such as. B. 4-hydroxybenzoic acid ester added; Oxidation-sensitive ingredients can be protected by adding antioxidants such as ascorbic acid, butyl methoxyphenol or tocopherol.
  • a third group of ingredients form special active ingredients for special shampoos, e.g. B. oils, herbal extracts, proteins, vitamins and lecithins in shampoos for quickly greasing, for particularly dry, for damaged or damaged hair.
  • Active ingredients in shampoos to combat dandruff usually have a broad growth-inhibiting effect against fungi and bacteria.
  • the fungistatic properties such. B. of pyrithione salts could be proven as the cause of good anti-dandruff effect.
  • the hair shampoos contain perfume oils to create a pleasant fragrance.
  • the shampoos can exclusively contain the alkoxylated fragrance alcohols according to the invention; however, it is also preferred if the hair shampoos contain not only these but also other fragrances. All the usual fragrances approved in hair shampoos can be used.
  • hair care products include a large number of different products, the main representatives of which are referred to as pre-treatment agents, hair lotions, hairdressing aids, hair rinses and spa packs, and whose composition is roughly broken down into basic substances, auxiliary substances and special active substances, as is the case with hair detergents.
  • the basic ingredients are fatty alcohols, especially cetyl alcohol (1-hexadecanol) and stearyl alcohol (1-octadecanol), waxes such as beeswax, wool wax (lanolin), wax and synthetic waxes, paraffins, petroleum jelly, paraffin oil and, above all, solvents, ethanol, 2-propanol and water. Excipients are emulsifiers, thickeners, preservatives, antioxidants, dyes and perfume oils. The most important group of special active ingredients in hair care products today are the quaternary ammonium compounds. A distinction is made between monomeric (e.g.
  • alkyltrimethylammonium halide with especially the lauryl, cetyl or stearyl group as the alkyl radical
  • polymeric quaternary ammonium compounds e.g. E.g .: quaternary cellulose ether derivatives or poly (N, N-dimethyl-3,4-methylene pyrrolidinium chloride)
  • Their effect in hair care products is based on the fact that the positive charge of the nitrogen atoms of this compound can attach to the negative charges of the hair keratin; Damaged hair contains more negatively charged acid groups due to its higher cysteic acid content and can therefore absorb more quaternary ammonium compounds.
  • cation-active care substances These, also referred to as “cation-active care substances” because of their cation-active character, have a smoothing effect on the hair, improve combability, reduce electrostatic charging, improve grip and shine.
  • the polymeric quaternary ammonium compounds adhere so well to the hair that their action is still effective after several washes.
  • Organic acids such as citric acid, tartaric acid or lactic acid are often used to adjust an acidic environment.
  • the water-soluble protein hydrolysates are well absorbed by the hair keratin due to their close chemical relationship.
  • the largest group of special active ingredients in hair care products form various plant extracts and plant Oils that have mostly been used for a long time without their effectiveness on the advertised effect has been scientifically proven in all cases.
  • aqueous preparations for the treatment of skin are in particular preparations for the care of human skin. This care begins with the cleaning for which soaps are primarily used. A distinction is made between solid, mostly lumpy and liquid soap. Accordingly, in a preferred embodiment, the cosmetic preparations are in the form of moldings which contain surface-active (surfactant) ingredients.
  • the most important constituents of such shaped articles are the alkali metal salts of the fatty acids of natural oils and fats, preferably with chains of 12 to 18 carbon atoms. Since lauric acid soaps foam particularly well, the lauric acid-rich coconut and palm kernel oils are preferred raw materials for fine soap manufacture.
  • the Na salts of the fatty acid mixtures are solid, the K salts are soft-pasty.
  • the dilute sodium or potassium hydroxide solution is added to the fat raw materials in a stoichiometric ratio so that an excess of alkali in the finished soap of max. 0.05% is present.
  • soaps are no longer made directly from fats, but from the fatty acids obtained through fat splitting.
  • Common soap additives are fatty acids, fatty alcohols, lanolin, lecithin, vegetable oils, partial glycerides and other fat-like substances for regreasing the cleansed skin, antioxidants such as ascorbyl palmitate or tocopherol to prevent the autoxidation of the soap (rancidity), complexing agents such as Nitrilotriacetate to bind traces of heavy metals that could catalyze autoxidative spoilage, perfume oils to achieve the desired fragrance notes, dyes to color the soap bars and, if necessary, special additives.
  • Soaps can also contain abrasive additives for cleaning heavily soiled hands.
  • a pH value of 8 to 10 is set in the wash liquor. This alkalinity neutralizes the skin's natural acid coat (pH 5 to 6). This is regressed relatively quickly with normal skin, but irritation can occur with sensitive or damaged skin.
  • Another disadvantage of soaps is their formation insoluble lime soaps in hard water. These disadvantages do not exist with Syndet soaps. They are based on synthetic anionic surfactants, which can be processed with soap substances, refatting agents and other additives into soap-like pieces. Their pH value can be varied within a wide range and is usually adjusted to pH 7 in a neutral manner or adjusted to pH 5.5 to suit the skin's acid coat. They have excellent cleaning power, foam in every water hardness, even in sea water, the proportion of lipid-replenishing additives must be significantly higher than with normal soaps due to their intensive cleaning and degreasing effect. Their disadvantage is the relatively high price.
  • Liquid soaps are based on both K salts of natural fatty acids and synthetic anionic surfactants. They contain less wash-active substances in aqueous solution than solid soaps, have the usual additives, optionally with viscosity-regulating components and pearlescent additives. Because of their convenient and hygienic use from dispensers, they are preferably used in public washrooms and the like. Wash lotions for particularly sensitive skin are based on mild-acting synthetic surfactants with additives of skin-care substances, pH neutral or slightly acidic (pH 5.5).
  • Facial lotions are mostly aqueous-alcoholic solutions with low surfactant levels and other skin-care substances.
  • Cleansing lotions, milks, creams and pastes are mostly based on O / W emulsions with relatively low levels of fat components with cleaning and care additives.
  • So-called scruffing and peeling preparations contain mildly keratolytic substances to remove the top dead skin-hom layers, e.g. T. with additives abrasive powder.
  • Bath salts and bath tablets are intended to soften, color and perfume the bathing water and generally do not contain any washing-active substances. By softening the bath water, they promote the cleaning power of soaps, but are primarily intended to have a refreshing effect and enhance the bathing experience. Bubble baths are of greater importance. With a higher content of lipid-replenishing and skin-care substances, one also speaks of cream baths.
  • shower baths In addition to bubble baths, shower baths have established themselves on the market since about 1970 and have exceeded their production volume since 1986. They are composed similarly to liquid shampoos, but contain special skin-care ingredients instead of hair-care agents. Combination products, suitable for skin and hair, have recently also appeared on the market.
  • the skin care that follows cleaning has two main goals: on the one hand, it should restore the skin's constituents, such as horny cells, skin lipids, acidifiers and water, which have been extracted in an uncontrolled manner, to the natural state of equilibrium; on the other hand, it should help the skin's natural aging process and possible damage counteract as much as possible by weather and environmental influences.
  • Preparations for Skin care and skin protection are offered in large numbers and in many forms of preparation. The most important are skin creams, lotions, oils and skin gels. The basis of the creams and lotions are emulsions in O / W (oil in water) or W / O (water in oil) form.
  • the main components of the oil, fat or lipid phase are fatty alcohols, fatty acids, fatty acid esters, waxes, petroleum jelly, paraffins and other fat and oil components of mainly natural origin.
  • the aqueous phase mainly contains moisture-regulating and moisture-preserving substances as essential skin care active ingredients, and also consistency and viscosity-regulating agents.
  • Other additives such as preservatives, antioxidants, complexing agents, perfume oils, colorants and special active ingredients are added to one of the two phases mentioned above depending on their solubility and their stability properties.
  • the selection of the emulsifier system is essential for the type of emulsion and its properties. It can be selected according to the HLB system.
  • the creams or lotions can be divided into “day creams” and "night creams".
  • Day creams are mostly built up as O / W emulsions, they are quickly absorbed into the skin without leaving an oily sheen; they are therefore called z. T. also as dry creams, matt creams or vanishing creams.
  • Night creams are mostly W / O emulsions, they are absorbed more slowly by the skin and often contain special active ingredients that are supposed to regenerate the skin during the night.
  • Some of these preparations are also referred to as "nutritional creams", although "cell metabolism” in the skin can only be “nourished” via the bloodstream; the term “nutrient cream” is therefore controversial.
  • So-called cold creams are mixed emulsions of the O / W and W / O type, with the oil phase predominating in quantity.
  • With classic cold cream the water, which in some cases was only unstably emulsified, was released during application and created a cooling effect through evaporation, which gave this preparation its name.
  • the large number of special active ingredients used in the skin care products and the effects attributed to them cannot be discussed in detail here. Mention should be made of milk protein products, egg yolk, lecithins, lipoids, phosphatides, cereal germ oils, vitamins - in particular vitamin F and the biotin formerly known as skin vitamin (vitamin H) as well as hormone-free placenta extracts. Hormones that were sometimes used in the past are no longer used because they are classified as active pharmaceutical ingredients and may not be used in cosmetic products.
  • Skin oils are among the oldest forms of skin care products and are still used today.
  • the basis is non-drying vegetable oils such as almond oil or olive oil, with additions of natural vitamin oils such as wheat germ oil or avocado oil as well as oily plant extracts from z. B. St. John's wort, chamomile u.
  • the addition of antioxidants against rancidity is essential, desired fragrance notes are achieved by perfume oils, an addition of paraffin oil or liquid fatty acid esters serves to optimize the application properties.
  • Skin gels are semi-solid, transparent products that are stabilized by appropriate gel formers.
  • a distinction is made between oleogels (water-free), hydrogels (oil-free) and oil / water gels.
  • the type selection depends on the desired application.
  • the oil / water gels contain high levels of emulsifier and have certain advantages over emulsions from both an aesthetic and application point of view.
  • Foot baths are said to have a good cleansing, refreshing, circulation-stimulating and invigorating effect, as well as deodorising and softening the cornea.
  • Foot bath additives are available as bath salts and bubble baths. They exist e.g. B. from base mixtures of sodium carbonate, sodium hydrogen carbonate and sodium perborate or sodium hexametaphosphate, sodium sulfate, sodium perborate and 1% sodium lauryl sulfate as a foam component with antiperspirant, deodorant, optionally bactericidal and / or fungicidal additives and fragrance and Dyes.
  • Foot powders applied after shampooing and / or sprinkled in stockings and shoes, should have a smoothing, cooling, moisture-absorbing, antiperspirant, antiseptic, deodorising and, if necessary, softening callus. They generally consist of 85% talc with the addition of silicic acid powder, aluminum hydroxychloride, salicylic acid and possibly bactericides, fungicides, deodorants and fragrances. Foot creams or foot balms are used for skin care and for massaging the foot and lower leg muscles. Foot creams are usually O / W emulsions from z. B.
  • a frame formulation consists of 25% paraffin, 2% stearic acid, 2% beeswax, 2% walnut, 2% glycerol monostearate, 0.5% 2, 2 ', 2 "nitrilotriethanol, 1% perfume oil, 0.2% 4-hydroxybenzoic acid and 65.3% water.
  • Nail fold tinctures are used to soften calluses in the nail folds and to keep the edges of the nails soft when the toenails grow in, mainly on the big toes.
  • a frame formulation is made up of 10% 2,2 ', 2 "nitrilotriethanol, 15% urea, 0.5% fatty alcohol polyglycol ether and 74.5% water
  • deodorant agents are agents for influencing body odor.
  • deodorant agents can mask, remove or destroy odors.
  • Unpleasant body odors arise when bacteria sweat decompose, especially in the warm, moist armpits, where microorganisms find good living conditions.
  • the main ingredients in deodorants are germ-inhibiting substances.
  • those germ-inhibiting substances are preferred which have a largely selective activity compared to those responsible for body odor Own bacteria.
  • preferred active ingredients only have a bacteriostatic effect and in no way completely kill the bacterial flora.
  • all suitable preservatives with a specific action against gram-positive bacteria can be directed to the germ-inhibiting agent.
  • Irgasan DP 300 trichlosan, 2,4,4'-trichloro-2'-hydroxydiphenyl ether
  • chlorhexidine (1, 1 '-hexamethylene bis (5- (4'-chloropheny! - biguanide)
  • 4,4'-trichlorocarbanilide Quaternary ammonium compounds are also suitable in principle. Because of their high antimicrobial activity, all these substances are preferably used only in small concentrations of about 0.1 to 0.3% by weight numerous odoriferous substances also have antimicrobial properties. Accordingly, such odoriferous substances with antimicrobial properties are preferably used in deodorants. Farnesol and phenoxyethanol are particularly to be mentioned here.
  • the deodorants according to the invention contain such themselves bacteriostatically active odoriferous substances.
  • the odorous substances can preferably be in the form of fragrance alcohol alkoxylates, but it is also possible for antibacterial fragrances to be present together with Fragrance alcohol alkoxylates are used and are thus present in mixtures with other fragrances.
  • Another group of essential ingredients of deodorants are enzyme inhibitors that inhibit the decomposition of sweat by enzymes, such as citric acid triethyl ester or zinc glycinate.
  • the essential ingredients of deodorants are also antioxidants, which are intended to prevent oxidation of the sweat components.
  • the cosmetic agent is a hair setting agent which contains polymers for setting. It is particularly preferred if at least one polyurethane is contained among the polymers.
  • the agents according to the invention can contain water-soluble polymers from the group of nonionic, anionic, amphoteric and zwitterionic polymers.
  • Water-soluble polymers are understood to be those polymers which are more than 2.5% by weight soluble in water at room temperature.
  • Water-soluble polymers preferred according to the invention are nonionic. Suitable nonionic polymers are, for example:
  • Polyvinylpyrrolidones such as those sold under the name Luviskol R (BASF). Polyvinylpyrrolidones are preferred non-ionic polymers in the context of the invention.
  • Vinyl pyrrolidone / vinyl ester copolymers such as those sold under the trademark Luviskol R (BASF).
  • Luviskol R VA 64 and Luviskol R VA 73, each vinylpyrrolidone / vinyl acetate copolymers, are particularly preferred nonionic polymers.
  • Cellulose ethers such as hydroxypropyl cellulose, hydroxyethyl cellulose and methyl hydroxypropyl cellulose, as are sold, for example, under the trademark Culminal ⁇ and Benecel R (AQUALON).
  • Suitable amphoteric polymers are, for example, the octylacrylamide / methyl methacrylate / tert available under the names Amphomer R and Amphomer R LV-71 (DELFT NATIONAL). Butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers.
  • Suitable zwitterionic polymers are, for example, the polymers disclosed in German patent applications DE 39 29 973, DE 21 50 557, DE 28 17 369 and DE 37 08 451.
  • Acrylamidopropyltrimethylammonium chloride / acrylic acid or methacrylic acid copolymers and their alkali and ammonium salts are preferred zwitterionic polymers.
  • Other suitable zwitterionic polymers are methacroylethyl betaine / methacrylate Copolymers which are commercially available under the name Amersette (AMERCHOL).
  • Anionic polymers suitable according to the invention include a .:
  • Vinyl acetate / crotonic acid copolymers as are commercially available, for example, under the names Resyn R (NATIONAL STARCH), Luviset R (BASF) and Gafset R (GAF).
  • Vinyl pyrrolidone / vinyl acrylate copolymers available, for example, under the trademark Luviflex (BASF).
  • a preferred polymer is the vinyl pyrrolidone / acrylate terpolymers available under the name Luviflex R VBM-35 (BASF).
  • Acrylic acid / ethyl acrylate / N-tert-butyl acrylamide terpolymers which are sold, for example, under the name Ultrahold R strong (BASF).
  • the hair treatment compositions according to the invention contain water-soluble polymers depending on the type of hair treatment composition which is not subject to any restrictions, preferably in amounts of 0.01 to 20% by weight, in particular 0.1 to 10% by weight, based on the total composition.
  • the polyurethanes and the water-soluble polymers are preferably present in the compositions according to the invention in a ratio of 1:10 to 10: 1.
  • a ratio of 2: 1 to 1: 1 has proven particularly suitable in many cases.
  • the hair setting agents according to the invention are, in particular, hair setting agents, hair sprays and hair dryer waves. Hair sprays are a particularly preferred embodiment of the hair fixative according to the invention.
  • the agents according to the invention can also be formulated as a foam aerosol using a propellant.
  • the preparations according to the invention which comprise one or more alkoxylated fragrance alcohols, show an optimized fragrance impression due to the content of the alkoxylated fragrance alcohols.
  • Preparations for which the alkoxylated fragrance alcohols produced in the way described in this application are distilled before being added to the preparation and thus freed from the fragrance-producing fragrance alcohol (the alkoxylated fragrance alcohol was almost odorless before the addition) call the alkoxylated fragrance alcohols a fragrance that already characterizes the preparation, which lasts for a long time and thus also survives a longer storage or transport time of the (possibly containing surfactant) preparation.
  • the scent is also well transferred to the object to be treated and adheres reliably there; it is released over a longer period of time and thus reliably leads to the desired fragrance. This can be described as surprising for detergents and cleaning agents as well as for cosmetic preparations.
  • fragrances are added to preparations containing surfactants in particular, in order to improve the overall aesthetic impression of the products and to provide the consumer with a technical, distinctive and unmistakable product in addition to the technical performance (washing, rinsing and cleaning results).
  • one or more further components which leave a scent impression can be added to the surfactant-containing preparations.
  • Individual fragrance compounds can be used as perfume oils or fragrances, for example the synthetic products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type.
  • Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, pt-butylcyclohexyl acetate, linalyl acetate, dimethylbenzyl carboxylate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethyl methylphenyl glycinate, allyl cyclohexyl hexylateylylyllylpylpropylate, melylalylylpylpropylate, melylalylylpylpropylate, melylalylylpylpropylate, melylalylatepylate, methylatelylylylpylate, methylatelylylylpylate, methyllalylatepylate, methylalylatepylate, methylalylatepylate, methylalylatepylate, methylalylatepylate,
  • the ethers include, for example, benzyl ethyl ether and ambroxan.
  • the aldehydes include e.g. B. linear alkanals with 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lileal and bourgeonal.
  • the ketones include the ionones, ⁇ -isomethyl ionone and methyl cedryl ketone.
  • Alcohols include anethole, citronellol, eugenol, geraniol, linalool, phenylethyl alcohol and terpineol.
  • the hydrocarbons mainly include terpenes such as limonene and pinene.
  • Mixtures of different fragrances are preferably used which are coordinated with one another in such a way that they together produce an appealing fragrance.
  • Such perfume oils can also contain natural fragrance mixtures, such as are obtainable from plant sources.
  • Natural fragrances include: extracts of flowers (lily, lavender, linden flowers, orange flowers, chamomile, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain, sage, lemon balm, mint, cinnamon leaves), Fruits (anise, coriander, caraway, nutmeg, cloves, juniper), fruit peels (bergamot, lemon, oranges), roots (macis, angelica, celery, cardamom, costus, iris, Calmus, vetiver), woods (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), needles and twigs (spruce, fir, pine, mountain pine), resins and Balsams (galbanum, elemi, benzoin, myrr
  • the fragrance content is usually up to 2% by weight of the total preparation.
  • the fragrances can be incorporated directly into the wash-active preparations; However, it can also be advantageous to apply the fragrances to carriers which increase the adhesion of the perfume to the laundry and ensure a long-lasting fragrance for the textiles due to a slower fragrance release.
  • Cyclodextrins for example, have proven themselves as such carrier materials.
  • the cyclodextrin-perfume complexes can also be coated with other auxiliaries.
  • fragrance impression of the above-mentioned fragrances additionally added to the (optionally surfactant-containing) preparations can be increased and lengthened if the optionally surfactant-containing preparations contain one or more alkoxylated fragrance alcohols of the general formula (I) with the case in which preparations containing surfactants only contain the aforementioned conventional fragrances.
  • the alkoxylated fragrance alcohols of the general formula (I) are therefore suitable as a fragrance booster, that is to say as a substance which is capable of sustainably intensifying the olfactory impressions of the components of a multi-substance system such as a preparation containing a surfactant or a mixture of two or more fragrances , This phenomenon is also surprising for detergent or cleaning agents as well as for cosmetic preparations.
  • the invention thus also relates to (optionally surfactant-containing) preparations according to the above description, that is to say both washing, rinsing, cleaning or softening agent preparations and also cosmetic preparation with a modified, in particular enhanced and / or extended, content by the content of one or more alkoxylated fragrance alcohols and / or qualitatively changed fragrance impression of the additionally contained fragrance (s).
  • the present invention further relates to a method for modifying the fragrance impression of one or more fragrance (s) contained in a multi-substance mixture by adding a quantity of one or more alkoxylated fragrance alcohols of the general formula (I) which modifies the fragrance impression
  • R 1 represents the scent alkyl radical of a scented alcohol of the formula R 1 OH;
  • R 2 and R 2 independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2 being hydrogen;
  • - n stands for an integer from 1 to 100.
  • the components used in such a (in particular surfactant-containing) preparation or in such a method, including the alkoxylated fragrance alcohols of the general formula (I) used according to the invention, are the components or compounds which have already been mentioned in detail above.
  • the alkoxylated fragrance alcohols the terpene alcohol alkoxylates mentioned above are particularly preferred.
  • the amount of the alkoxylated fragrance alcohol (s) modifying the fragrance impression is in the range from 0.001 to 20% by weight.
  • the modification of the fragrance impression is an intensification or intensification of the fragrance of the one or more fragrance (s) present in the multi-substance mixture, an extension of the fragrance of the one or more fragrance (s) present in the multi-substance mixture , a qualitative change in the fragrance of the one or more fragrances (s) present in the multi-substance mixture or a combination of two or more of the processes mentioned.
  • the modification can relate both to the modification of the fragrance of the one or more fragrance (s) in the preparation and to the modification of the fragrance which the preparation transmits to an object and which follows from the transmission of this object the environment is released.
  • the invention also relates to washing processes in which one or more surfactant-containing preparations for washing, as described above in detail with regard to their components, are applied to the washing liquor and the laundry, in particular textiles, is treated therewith.
  • the washing process can in particular be a machine washing process which is carried out in a conventional washing machine.
  • the surfactant-containing preparation or several surfactant-containing preparations are placed in the washing-in chamber of the washing machine and / or in containers, nets or the like to be placed in the items to be washed, which are permeable to water or the washing liquor, and are optionally washed into the washing drum with water and since- when brought into contact with the laundry.
  • the washing process can be carried out at a wide variety of temperatures and on a wide variety of textiles.
  • one or more surfactant-containing preparation (s) according to the invention in a vessel suitable for washing by hand, where it is brought into contact with water and / or the washing liquor and subsequently with the laundry becomes.
  • the effects desired according to the invention are observed, that is to say, when only one or more alkoxylated fragrance alcohols are present, a long-lasting fragrance originating from the corresponding alkoxylated fragrance alcohol is found in the wash liquor and on the damp and dry laundry items, while with the additional presence of fragrances other than the alkoxylated fragrance alcohols, the fragrance of which is strengthened / intensified and also extended.
  • the present invention further relates to rinsing processes in which one or more surfactant-containing preparations for rinsing, as described in detail above with regard to their components, are applied to the rinsing liquor and the items to be washed, in particular dishes, cutlery, glasses, etc ., treated with it.
  • the washing process can in particular be a machine washing process which is carried out in a conventional dishwasher.
  • the surfactant-containing preparation or several surfactant-containing preparations are to be placed in the dishwashing chamber of the dishwasher and / or in the vicinity of the wash ware, containers which are permeable to water or the wash liquor, nets, foils, foils or the like soluble in the wash liquor given, optionally flushed with water into the dishwasher's washing compartment and brought into contact therewith or afterwards with the items to be washed.
  • the items to be washed can be crockery, cutlery, glassware, metals from pots or pans, wood material or the like, but also laboratory equipment, medical equipment etc. and can be treated at a wide variety of temperatures - depending on the degree of contamination or cleaning requirements.
  • one or more surfactant-containing preparation (s) according to the in a container suitable for washing by hand, where it is brought into contact with water and / or the washing liquor and subsequently with the wash ware.
  • the effects sought according to the invention are observed, that is to say, when only one or more alkoxylated fragrance alcohols are present, a long-lasting fragrance originating from the corresponding alkoxylated fragrance alcohol is found in the wash liquor and on the damp and dry wash items, while with the additional presence of fragrances other than the alkoxylated fragrance alcohols, the fragrance of which is intensified / intensified and also extended.
  • the present invention further relates to cleaning processes in which one or more surfactant-containing preparation (s) for cleaning, as described in detail above with regard to their components, are applied to the cleaning liquor and the items to be cleaned or surfaces to be cleaned are treated with them.
  • the cleaning method can in particular be a mechanical cleaning method which is carried out using conventional cleaning machines.
  • the surfactant-containing preparation or several surfactant-containing preparations are added to the washing-up chamber or the suction vessel of a cleaning machine and / or directly to the cleaning liquor, if necessary flushed into the pressure chamber of the cleaning machine with water and then or thereafter with the items to be cleaned or with brought into contact with the surfaces to be cleaned.
  • the items to be cleaned can be objects of all kinds, such as pieces of furniture, sanitary ware, devices, vehicles, etc., but also surfaces of all kinds, and these can be treated at different temperatures, depending on the degree of contamination or cleaning requirements.
  • one or more surfactant-containing preparation (s) according to the invention into a vessel suitable for cleaning by hand, where it is washed with water and / or the cleaning liquor and subsequently with the one to be cleaned Is brought into good contact.
  • the present invention further relates to finishing agents, in which one or more surfactant-containing preparation (s) for finishing, as described above in detail with regard to its components (s), are applied to the usually aqueous liquor intended for finishing and the laundry, in particular Textiles, treated with it.
  • the finishing process can in particular be a mechanical finishing process which is carried out in a conventional washing machine or machine for dry cleaning.
  • the surfactant-containing preparation or several surfactant-containing preparations are added to the washing-in chamber of the washing machine or the cleaning machine or into solvent mixtures containing water, organic solvents or the washing or cleaning liquor, containers, nets or the like, if appropriate Water or solvent is flushed into the washing-up chamber of the washing or cleaning machine and in the process or thereafter brought into contact with the items to be washed or cleaned.
  • the items to be washed or cleaned can be textiles, blankets, duvets etc. and can be treated at a wide variety of temperatures - depending on the degree of soiling or cleaning requirements.
  • one or more surfactant-containing preparations) according to the invention into a vessel suitable for applying a finishing agent by hand, where they are mixed with water and / or the washing or cleaning liquor and subsequently with is brought into contact with the goods to be finished.
  • the effects sought according to the invention are observed, ie in the presence of one or of several alkoxylated fragrance alcohols, a long-lasting fragrance originating from the corresponding alkoxylated fragrance alcohol (s) is found on the laundry and on the moist and dry laundry, while in the presence of fragrances other than the alkoxylated fragrance alcohols, their fragrance is strengthened / intensified and is also extended.
  • the present invention also relates to cosmetic treatment methods in which one or more (possibly surfactant-containing) preparations) for a cosmetic treatment, as described above in detail with regard to its components, are applied to the human body, e.g. B. the skin, or parts thereof, for example the hair, applied and this (s) treated with it.
  • the cosmetic treatment process is usually carried out with the body (or parts thereof) being brought into direct contact with one or more (optionally surfactant-containing) preparation (s) according to the invention.
  • the (possibly surfactant-containing) preparations can be applied to the body or parts thereof with carriers (cotton pads, tissue towels, etc.). In both cases, the effects sought according to the invention are observed; H.
  • fragrances other than the alkoxylated fragrance alcohols when only one or more alkoxylated fragrance alcohols are present, a long-lasting fragrance is found on the body, while in the additional presence of fragrances other than the alkoxylated fragrance alcohols, their fragrance is strengthened / intensified and also extended and / or qualitatively changed.
  • alkoxylated fragrance alcohols of the general formula (I) in hair cosmetic compositions leads to a considerable improvement in the tactile properties of the hair.
  • hair cosmetics which comprise one or more alkoxylated fragrance alcohols, not only is the hair handle and its combability and the shine and the handle of the hair significantly improved, but it is also achieved that the hair smells noticeably better or the fragrance impression of perfume oils contained in the hair cosmetic products is intensified and sustainably extended.
  • the invention also relates to a method for improving the tactile properties of the hair, in which the hair is treated with at least one cosmetic preparation which comprises one or more alkoxylated fragrance alcohols of the general formula (I) in an amount which improves the tactile properties of the hair.
  • the invention further relates to hair cosmetic compositions which, in addition to ingredients known per se, comprise one or more alkoxylated fragrance alcohols of the general formula (I),
  • R 1 represents the scent alkyl radical of a scented alcohol of the formula R 1 OH;
  • R 2 and R 2 ' independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2 being hydrogen;
  • - n stands for an integer from 1 to 100.
  • the radical R 1 in the general formula (I) represents an isononyl radical or the terpene radical of a terpene alcohol R 1 OH.
  • alkoxylated terpene alcohols of the above general formula (I) are particularly preferably used, in which R 1 is selected from the group geranyl, citronellyl, tetrahydrogeranyl, linaloyl, dihydrolinaloyl, tetrahydrolinaloyl, neryl, myrcenyl, dihydromyrcenyl, lavendulyl, farnesyl, nerolidyl , Menthyl, isopulegyl, terpinyl, thymyl, tetrahydromuguyl, 2,5-dimethylhept 2-yl and phen-ylethyl.
  • Hair cosmetic preparations containing alkoxylated fragrance alcohols of the general formula (I), in which R 1 has one of the meanings mentioned above, can achieve a significant improvement in the tactile properties of the hair in cosmetic treatment processes; it can also be used to apply long-lasting intensive fragrance notes to the hair.
  • n is an integer in the range from 5 to 20 and by a maximum of ⁇ 3, preferably by a maximum of ⁇ 2, around a certain Numerical value fluctuates or k and m in the general formula (Ia) stand for integers in the range from 5 to 20 and fluctuate by at most ⁇ 3, preferably at most ⁇ 2, by a certain numerical value.
  • hair cosmetic preparations with alkoxylated fragrance alcohols which can advantageously be used on account of the good fragrance properties and the improvement of the tactile hair properties are hair cosmetic preparations with the compounds represented by the formulas (1.1.) To (I.8.) below:
  • R 2 and R 2 ' independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2 being hydrogen and n being an integer in the range from 5 to 20.
  • one or more alkoxylated fragrance alcohols of the general formula (I) are used in hair cosmetic preparations in an amount of 0.001 to 20% by weight, preferably in an amount of 0.01 to 5% by weight, particularly preferably in an amount of 0 , 02 to 3 wt .-% and in particular in an amount of 0.05 to 2 wt .-%, based on the hair cosmetic preparation used.
  • the invention also relates to a method for improving the tactile properties of the hair, in which the hair is treated with at least one cosmetic preparation which comprises one or more alkoxylated fragrance alcohols of the general formula (I),
  • R 1 represents the scent alkyl radical of a scented alcohol of the formula R 1 OH;
  • R 2 and R 2 ' independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R 2 being hydrogen;
  • - n stands for an integer from 1 to 100
  • alkoxylated fragrance alcohols of the general formula (I) used in the preparations for the cosmetic treatment of the hair reference can be made to the above statements regarding the alkoxylated fragrance alcohols.
  • the hair in particular the human hair, is treated with at least one cosmetic preparation which contains one or more alkoxylated fragrance alcohols of the above general formula (I) in an amount which improves the tactile properties of the hair .
  • the exact amount depends on the agent used, the ingredients of the preparation used for the treatment and also the form of application and is, for example - without being understood as a restriction - for a hair shampoo in the range from 0.1 to 10% by weight. %, preferably in the range from 0.5 to 5% by weight and in particular in the range from 0.7 to 2% by weight, based on the total weight of the hair cosmetic preparation, in this case the shampoo.
  • amounts in the range from 0.5 to 15% by weight preferably in the range from 1 to 10% by weight and in particular in the range from 2 to 10% by weight
  • the invention also relates to hair cosmetic compositions comprising, in addition to ingredients known per se, one or more alkoxylated fragrance alcohols of the general formula (I),
  • R 2 and R 2 ' independently of one another are hydrogen or a CH 3 radical, at least one of the radicals R 2 and R being hydrogen;
  • - n stands for an integer from 1 to 100.
  • the hair cosmetic agents or preparations according to the invention can be hair washing agents, hair care agents, hair setting agents and hair shaping agents as well as hair coloring agents and hair removal agents.
  • the most important group of these are shampoos or hair shampoos, hair care products such as hair rinses, hair lotions, hairdressing aids and spa packs, and hair setting agents such as hair sprays and hair lacquers.
  • alkoxylated fragrance alcohols in particular the terpene alcohol alkoxylates, of the above general formula (I), in which the number of ethoxy groups and propoxy groups has a narrow range
  • liquid detergent formulations Rp. 3 and Rp. 4 given in Table 2 below were used to check whether the fragrance could be improved by terpane alcohol ethoxylates according to the invention.
  • the only difference between the two recipes is the type of alcohol alkoxylate used.
  • Strands of hair (2 g) were pre-cleaned with a fragrance-free aqueous surfactant solution and then rinsed thoroughly. Then 1 g of the recipes from Table 3 below was applied to the strands of hair per gram of hair and also thoroughly rinsed out.
  • the strands of hair were assessed in terms of their fragrance intensity.
  • a panel of 10 test persons consistently assessed the fragrance intensity on the strands of hair treated with the preparations / recipes Rp. 6 and Rp. 7 as stronger than on the strands of hair treated with the preparation / recipe Rp. 5.
  • a free-flowing premix was produced by mixing the formulation components mentioned below in a Lödige mixer, which was compacted and plasticized in an extruder.
  • fragrance pearl formulations 8 and 9 produced were compared in their fragrance impression on test laundry. It was found that when using recipe 9 (5% in a perfume oil-free standard UWM recipe) the laundry had a more intense and pleasant fragrance impression when wet and dry than when using recipe 8.
  • Example 13 Cosmetic emulsion containing fragrance alcohol ethoxylate
  • a cosmetic emulsion was prepared by stirring the components according to Table 5 below:
  • Strands of hair (2 g) were pre-cleaned with an aqueous surfactant solution and then rinsed thoroughly.
  • Example 15 The hair treated with the formulation of Example 15 containing the alkoxylated scented alcohol Geraniol + 6 EO was easier to comb and showed advantages in properties such as good smoothness and feel.
  • the sensory profile is shown in the attached FIG. 1. It was determined by the sensory assessment method known to the person skilled in the art. In FIG. 1, “Geraniol 6 EO” is to be understood as the formulation according to Example 15, under “placebo” the formulation according to Example 14.
  • Hair rinses are often used in practice to give the hair special cosmetic properties such as to give an improved grip, better combability, shine or good stylability.
  • non-ionic emulsifiers and thickeners e.g. Lipids and the like other cosmetic active ingredients.
  • cationic compounds and care ingredients e.g. Lipids and the like other cosmetic active ingredients.
  • a disadvantage of the formulations of the prior art is the generally more or less great strain on the hair due to the conditioning compounds used, which manifests itself in noticeable residues in the hair, a certain amount of sticking and reduced hair volume.
  • 0.5 g / g of hair was applied from each of the present formulations S1 and S2. After an exposure time of 20 min, the rinsing was carried out with warm tap water and, after drying, the sensory properties of the strands of hair were checked by a test panel.
  • the hair treated with formulation S2 like the hair treated with formulation S1, had good combability, soft tips and a pleasant feel.
  • the strands treated with formulation S2 were better assessed with regard to residues in the hair and hair volume.

Abstract

La présente invention concerne des alcools de substances odorantes alcoxylés de formule générale (I) R1O - [CH(R?2)-CH(R2)-O-]¿n-R3 dans laquelle : R1 est un radical alkyle de substance odorante d'un alcool de substance odorante de formule R?1OH; R2 et R2'¿ sont indépendamment hydrogène ou un radical CH¿3?, au moins l'un des radicaux R?2 et R2'¿ étant hydrogène ; R3 est hydrogène, un radical alkyle ayant de 1 à 60 atomes de carbone, un radical (C=O)R3', R3' étant hydrogène ou un radical alkyle ayant de 1 à 60 atomes de carbone, ou est R1; et n est un nombre entier allant de 1 à 100. Cette invention concerne également un procédé permettant la préparation desdits alcools, ainsi que leur utilisation dans des agents de lavage, de rinçage, de nettoyage et d'avivage, ainsi dans des préparations cosmétiques.
EP01933723A 2000-03-20 2001-03-17 Alcools de substances odorantes alcoxyles et leur utilisation Withdrawn EP1268382A2 (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
DE10013764 2000-03-20
DE10013766A DE10013766A1 (de) 2000-03-20 2000-03-20 Duftoptimierte Zubereitungen
DE10013762 2000-03-20
DE10013764A DE10013764A1 (de) 2000-03-20 2000-03-20 Verwendung von Duftalkoholalkoxylaten in haarkosmetischen Mitteln
DE10013762A DE10013762A1 (de) 2000-03-20 2000-03-20 Alkoxylierte Duftalkohole, insbesondere Terpenalkohole, und ihre Verwendung in Wasch-, Spül- oder Reinigungsmitteln oder kosmetischen Zubereitungen
DE10013766 2000-03-20
PCT/EP2001/003086 WO2001070661A2 (fr) 2000-03-20 2001-03-17 Alcools de substances odorantes alcoxyles et leur utilisation

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EP1268382A2 true EP1268382A2 (fr) 2003-01-02

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EP (1) EP1268382A2 (fr)
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WO (1) WO2001070661A2 (fr)

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Publication number Priority date Publication date Assignee Title
DE10013763A1 (de) * 2000-03-20 2001-10-18 Henkel Kgaa Verwendung von Duftalkoholalkoxylaten in Wasch- und Reinigungsmitteln und kosmetischen Zubereitungen
CN102276428B (zh) * 2010-06-10 2015-11-25 克施乐化学工厂两合公司 制备醇乙氧基化物的方法及产品
WO2013113831A1 (fr) * 2012-01-31 2013-08-08 Basf Se Alcoxylates de farnésols le cas échéant hydrogénés et leur utilisation
US20130197275A1 (en) * 2012-01-31 2013-08-01 Wolfgang Spiegler Alkoxylates of optionally hydrogenated farnesols and use thereof
BR112014018842A2 (pt) * 2012-01-31 2018-09-11 Basf Se alcoxilato de farnesol, processo para a preparação de um composto, uso de pelo menos um composto ou de um produto de reação, composição, e, método de lavagem, enxágue, limpeza ou acabamento
JP6362225B2 (ja) * 2016-08-08 2018-07-25 曽田香料株式会社 害虫忌避剤

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Publication number Priority date Publication date Assignee Title
CS253437B1 (en) * 1986-04-11 1987-11-12 Milan Paulovic Tenzide with low frothiness and pleasent aroma
FR2721921B1 (fr) * 1994-07-01 1996-10-31 Rhone Poulenc Chimie Derives d'origine terpenique, composition tensioactive et/ou parfumante en contenant et formulation detergente a base de cette composition
JP2000512663A (ja) * 1996-02-21 2000-09-26 ジボーダン―ルール（アンテルナシヨナル）ソシエテ アノニム フレイグランス先駆体
DE19812245A1 (de) * 1998-03-20 1999-09-23 Clariant Gmbh Neue Terpenether und deren Anwendungen
DE19841147A1 (de) * 1998-09-09 2000-03-16 Henkel Kgaa Kiselsäureester

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