EP0799885A1 - Composés bétaine ester des aclcools actifs - Google Patents

Composés bétaine ester des aclcools actifs Download PDF

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Publication number
EP0799885A1
EP0799885A1 EP96302291A EP96302291A EP0799885A1 EP 0799885 A1 EP0799885 A1 EP 0799885A1 EP 96302291 A EP96302291 A EP 96302291A EP 96302291 A EP96302291 A EP 96302291A EP 0799885 A1 EP0799885 A1 EP 0799885A1
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EP
European Patent Office
Prior art keywords
hydrochloride
ester
oxoethyl
composition according
aqueous acidic
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Withdrawn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
EP96302291A
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German (de)
English (en)
Inventor
Marc Johan Declercq
Hugo Jean Demeyere
Arnaud Pierre Struillou
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Procter and Gamble Co
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Procter and Gamble Co
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
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to EP96302291A priority Critical patent/EP0799885A1/fr
Priority to AU25908/97A priority patent/AU2590897A/en
Priority to BR9710416A priority patent/BR9710416A/pt
Priority to CN97195159A priority patent/CN1220693A/zh
Priority to CA002250837A priority patent/CA2250837C/fr
Priority to PCT/US1997/004959 priority patent/WO1997036978A1/fr
Priority to US09/155,779 priority patent/US5958870A/en
Priority to JP53540697A priority patent/JP3770916B2/ja
Priority to ARP970101299A priority patent/AR008583A1/es
Priority to ZA9702775A priority patent/ZA972775B/xx
Publication of EP0799885A1 publication Critical patent/EP0799885A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/65—Mixtures of anionic with cationic compounds
    • 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/507—Compounds releasing perfumes by thermal or chemical activation

Definitions

  • the present invention relates to betaine ester compounds of active alcohols. More particularly, it relates to stabilised betaine ester compounds of active alcohols in an acidic environment such as in a fabric softener composition.
  • betaine ester compounds are effective in the slow release of perfume, it has now been found that in an acidic environment such as in acidic product, the described compounds hydrolyse upon storage to release their perfume component, therefore reducing the amount of perfume alcohol released upon and after the washing or cleaning process.
  • acidic environment it is meant a pH value of less than 7.0.
  • the formulator of a laundry and/or cleaning compositions is thus faced with the challenge of formulating a compound which is stable in an acidic environment but which still produces a slow release of the active alcohol (e.g perfume) upon and after the washing or cleaning process.
  • active alcohol e.g perfume
  • betaine ester compounds of active alcohols in combination with a surfactant, wherein said betaine esters at a concentration of from 0.01% to 10% by weight are predominantly in the form of micelles, and/or are capable of being incorporated into micelles, overcomes the problem.
  • said betaine esters have at least one long alkyl chain.
  • the present invention encompasses acidic compositions comprising betaine ester compounds of active alcohol components having a long alkyl chain, which at a concentration of from 0.01% to 10% by weight are predominantly in the form of micelles, and/or are capable of being incorporated into micelles, in combination with a surfactant.
  • a cationic surfactant is preferred.
  • betaine ester compounds with at least one long alkyl chain provide said betaine esters with a hydrophobic character which enable them to be rearranged in micelle form and/or to be incorporated into micelles, thereby protecting the ester bond from hydrolysis by the acidic environment.
  • the term "acidic aqueous composition” includes compositions having a pH value below or equal to 7.0, whereby the pH is measured at 20°C in the neat liquid product.
  • slow release is meant release of the active component (e.g perfume) over a longer period of time than by the use of the active (e.g perfume) itself. Accordingly, the slow release concept and storage stability advantage of the invention may be applied to other active alcohol components such as a flavour alcohol ingredient, a pharmaceutical alcohol active or a biocontrol alcohol agent and any other active alcohol component where a slow release of said active component is necessary.
  • the present invention relates to an aqueous acidic composition
  • an aqueous acidic composition comprising
  • the betaine ester is a hydrophobic betaine ester of formula:
  • a process for preparing said acidic composition comprises the following steps:
  • An essential component of the invention is a betaine ester of an active alcohol, which, at a concentration of from 0.01% to 10% by weight in said composition, is predominantly in the form of micelles, and/or is capable of being incorporated into micelles, e.g a micelle can be composed of 100% betaine esters or mixed betaine esters/surfactants.
  • the betaine ester compounds of an active alcohol have the general formula below: wherein each R 1 , R 2 , R 3 independently, is selected from hydrogen, alkyl group, aryl group, and with the proviso that where each R1, R2 and R3, independently, are only selected from hydrogen, aryl or alkyl groups, then at least one of R1, R2 or R3 is an alkyl or aryl group having at least 8 carbon atoms,
  • each n 2 is an integer lying in the range of 0 to 6.
  • each n3, independently, is an integer of value 1 or 2, more preferably 1.
  • R 1 , R 2 , R 3 are each, independently selected from H, alkyl chain having from 1 to 20 carbon atoms, with the proviso that at least one of R 1 , R 2 or R 3 is an alkyl group having at least 8 carbon atoms.
  • R' 1 , R' 2 are, each, independently selected from H, alkyl chain having 1 to 3 carbon atoms, phenyl.
  • the R group which is hydrophobic in nature, is the organic chain of an active alcohol, said active alcohol being selected from a flavour alcohol ingredient, a pharmaceutical alcohol active, a biocontrol alcohol agent, a perfume alcohol component and mixtures thereof.
  • Flavour ingredients include spices, flavour enhancers that contribute to the overall flavour perception.
  • Pharmaceutical actives include drugs.
  • Biocontrol agents include biocides, antimicrobials, bactericides, fungicides, algaecides, mildewcides, disinfectants, antiseptics, insecticides, vermicides, plant growth hormones.
  • Perfume alcohol components include components having odoriferous properties.
  • the R group is the organic chain of a perfume alcohol, said alcohol being selected from 2-phenoxyethanol, phenylethylalcohol, geraniol, citronellol, 3-methyl-5-phenyl-1-pentanol, 2,4-dimethyl-3-cyclohexene-1-methanol, linalool, tetrahydrolinalool, 1,2-dihydromyrcenol, hydroxycitronellal, farnesol, menthol, eugenol, vanilin, cis-3-hexenol, terpineol and mixtures thereof.
  • a perfume alcohol said alcohol being selected from 2-phenoxyethanol, phenylethylalcohol, geraniol, citronellol, 3-methyl-5-phenyl-1-pentanol, 2,4-dimethyl-3-cyclohexene-1-methanol, linalool, tetrahydrolinalool, 1,2-dihydromyr
  • More preferred R groups are selected from the organic chain of a perfume alcohol, said alcohol being selected from geraniol, citronellol, linalool, dihydromyrcenol and mixtures thereof.
  • Preferred compounds for the purpose of the invention are selected from geranyloxycarbonyl-N,N-dimethyl-N-dodecylmethanaminium bromide or chloride; citronellyloxycarbonyl-N,N-dimethyl-N-dodecylmethanaminium bromide or chloride; linalyloxycarbonyl-N,N-dimethyl-N-dodecylmethanaminium bromide or chloride; dihydromyrcenyloxycarbonyl-N,N-dimethyl-N-dodecylmethanaminium bromide or chloride.
  • N-dodecylglycine geranyl ester hydrobromide or hydrochloride N-dodecylglycine citronellyl ester hydrobromide or hydrochloride
  • N-dodecylglycine linalyl ester hydrobromide or hydrochloride N-dodecylglycine dihydromyrcenyl ester hydrobromide or hydrochloride.
  • N,N-dioctylglycine geranyl ester hydrobromide or hydrochloride N,N-dioctylglycine citronellyl ester hydrobromide or hydrochloride
  • N,N-dioctylglycine linalyl ester hydrobromide or hydrochloride N,N-dioctylglycine dihydromyrcenyl ester hydrobromide or hydrochloride.
  • N,N-didodecylglycine geranyl ester hydrobromide or hydrochloride N,N-didodecylglycine citronellyl ester hydrobromide or hydrochloride, N,N-didodecylglycine linalyl ester hydrobromide or hydrochloride; N,N-didodecylglycine dihydromyrcenyl ester hydrobromide or hydrochloride.
  • N-butyl-N-(2-geranyloxy-2-oxoethyl)glycine geranyl ester hydrobromide or hydrochloride N-butyl-N-(2-citronellyloxy-2-oxoethyl)glycine citronellyl ester hydrobromide or hydrochloride
  • N-butyl-N-(2-dihydromyrcenyloxy-2-oxoethyl)glycine dihydromyrcenyl ester hydrobromide or hydrochloride N-butyl-N-(2-geranyloxy-2-oxoethyl)glycine geranyl ester hydrobromide or hydrochloride.
  • N-dodecyl-N-(2-geranyloxy-2-oxoethyl)glycine geranyl ester hydrobromide or hydrochloride N-dodecyl-N-(2-citronellyloxy-2-oxoethyl)glycine citronellyl ester hydrobromide or hydrochloride
  • N-dodecyl-N-(2-dihydromyrcenyloxy-2-oxoethyl)glycine dihydromyrcenyl ester hydrobromide or hydrochloride N-dodecyl-N-(2-geranyloxy-2-oxoethyl)glycine geranyl ester hydrobromide or hydrochloride.
  • N,N-bis(2-geranyloxy-2-oxoethyl)glycine geranyl ester hydrobromide or hydrochloride N,N-bis(2-citronellyloxy-2-oxoethyl)glycine citronellyl ester hydrobromide or hydrochloride
  • N,N-bis(2-dihydromyrcenyloxy-2-oxoethyl)glycine dihydromyrcenyl ester hydrobromide or hydrochloride N,N-bis(2-geranyloxy-2-oxoethyl)glycine geranyl ester hydrobromide or hydrochloride.
  • levels of incorporation of said betaine ester compounds of active alcohols, into the acidic composition are from 0.01% to 8%, more preferably 0.05% to 5%, and most preferably from 0.1% to 2%, by weight of the total composition.
  • the other essential component of the invention is a surfactant.
  • Such surfactant are selected from anionic, nonionic, cationic, amphoteric and zwiterrionic surfactants.
  • any anionic surfactants useful for detersive purposes can be included in the compositions. These can include salts (including, for example, sodium, potassium, ammonium, and substituted ammonium salts such as mono-, di- and triethanolamine salts) of the anionic sulfate, sulfonate, carboxylate and sarcosinate surfactants.
  • salts including, for example, sodium, potassium, ammonium, and substituted ammonium salts such as mono-, di- and triethanolamine salts of the anionic sulfate, sulfonate, carboxylate and sarcosinate surfactants.
  • anionic surfactants include the isethionates such as the acyl isethionates, N-acyl taurates, fatty acid amides of methyl tauride, alkyl succinates and sulfosuccinates, monoesters of sulfosuccinate (especially saturated and unsaturated C 12 -C 18 monoesters) diesters of sulfosuccinate (especially saturated and unsaturated C 6 -C 14 diesters), N-acyl sarcosinates.
  • Resin acids and hydrogenated resin acids are also suitable, such as rosin, hydrogenated rosin, and resin acids and hydrogenated resin acids present in or derived from tallow oil.
  • Anionic sulfate surfactants suitable for use herein include the linear and branched primary alkyl sulfates, alkyl ethoxysulfates, fatty oleyl glycerol sulfates, alkyl phenol ethylene oxide ether sulfates, the C 5 -C 17 acyl-N-(C 1 -C 4 alkyl) and -N-(C 1 -C 2 hydroxyalkyl) glucamine sulfates, and sulfates of alkylpolysaccharides such as the sulfates of alkylpolyglucoside (the nonionic nonsulfated compounds being described herein).
  • Alkyl ethoxysulfate surfactants are preferably selected from the group consisting of the C 6 -C 18 alkyl sulfates which have been ethoxylated with from about 0.5 to about 20 moles of ethylene oxide per molecule. More preferably, the alkyl ethoxysulfate surfactant is a C 6 -C 18 alkyl sulfate which has been ethoxylated with from about 0.5 to about 20, preferably from about 0.5 to about 5, moles of ethylene oxide per molecule.
  • Anionic sulfonate surfactants suitable for use herein include the salts of C 5 -C 20 linear alkylbenzene sulfonates, alkyl ester sulfonates, C 6 -C 22 primary or secondary alkane sulfonates, C 6 -C 24 olefin sulfonates, sulfonated polycarboxylic acids, alkyl glycerol sulfonates, fatty acyl glycerol sulfonates, fatty oleyl glycerol sulfonates, and any mixtures thereof.
  • Anionic carboxylate surfactants suitable for use herein include the alkyl ethoxy carboxylates, the alkyl polyethoxy polycarboxylate surfactants and the soaps ('alkyl carboxyls'), especially certain secondary soaps as described herein.
  • Preferred alkyl ethoxy carboxylates for use herein include those with the formula RO(CH 2 CH 2 0) x CH 2 C00 - M + wherein R is a C 6 to C 18 alkyl group, x ranges from O to 10, and the ethoxylate distribution is such that, on a weight basis, the amount of material where x is 0 is less than about 20 %, and the amount of material where x is greater than 7, is less than about 25 %, the average x is from about 2 to 4 when the average R is C 13 or less, and the average x is from about 3 to 10 when the average R is greater than C 13 , and M is a cation, preferably chosen from alkali metal, alkaline earth metal, ammonium, mono-, di-, and tri-ethanol-ammonium, most preferably from sodium, potassium, ammonium and mixtures thereof with magnesium ions.
  • the preferred alkyl ethoxy carboxylates are those where R is a C 12 to C 18 al
  • Alkyl polyethoxy polycarboxylate surfactants suitable for use herein include those having the formula RO-(CHR 1 -CHR 2 -O)-R 3 wherein R is a C 6 to C 18 alkyl group, x is from 1 to 25, R 1 and R 2 are selected from the group consisting of hydrogen, methyl acid radical, succinic acid radical, hydroxysuccinic acid radical, and mixtures thereof, wherein at least one R 1 or R 2 is a succinic acid radical or hydroxysuccinic acid radical, and R 3 is selected from the group consisting of hydrogen, substituted or unsubstituted hydrocarbon having between 1 and 8 carbon atoms, and mixtures thereof.
  • Preferred soap surfactants are secondary soap surfactants which contain a carboxyl unit connected to a secondary carbon.
  • the secondary carbon can be in a ring structure, e.g. as in p-octyl benzoic acid, or as in alkyl-substituted cyclohexyl carboxylates.
  • the secondary soap surfactants should preferably contain no ether linkages, no ester linkages and no hydroxyl groups. There should preferably be no nitrogen atoms in the head-group (amphiphilic portion).
  • the secondary soap surfactants usually contain 11-15 total carbon atoms, although slightly more (e.g., up to 16) can be tolerated, e.g. p-octyl benzoic acid.
  • the species M can be any suitable, especially water-solubilizing, counterion.
  • Especially preferred secondary soap surfactants for use herein are water-soluble members selected from the group consisting of the water-soluble salts of 2-methyl-1-undecanoic acid, 2-ethyl-1-decanoic acid, 2-propyl-1-nonanoic acid, 2-buty-1-octanoic acid and 2-pentyl-1-heptanoic acid.
  • alkali metal sarcosinates of formula R-CON (R 1 ) CH 2 COOM, wherein R is a C 5 -C 17 linear or branched alkyl or alkenyl group, R 1 is a C 1 -C 4 alkyl group and M is an alkali metal ion.
  • R is a C 5 -C 17 linear or branched alkyl or alkenyl group
  • R 1 is a C 1 -C 4 alkyl group
  • M is an alkali metal ion.
  • nonionic surfactants useful for detersive purposes can be included in the compositions.
  • exemplary, non-limiting classes of useful nonionic surfactants are listed below.
  • Polyhydroxy fatty acid amides suitable for use herein are those having the structural formula R 2 CONR 1 Z wherein: R1 is H, C 1 -C 4 hydrocarbyl, 2-hydroxy ethyl, 2-hydroxy propyl, or a mixture thereof, preferable C1-C4 alkyl, more preferably C 1 or C 2 alkyl, most preferably C 1 alkyl (i.e., methyl); and R 2 is a C 5 -C 31 hydrocarbyl, preferably straight-chain C 5 -C 19 alkyl or alkenyl, more preferably straight-chain C 9 -C 17 alkyl or alkenyl, most preferably straight-chain C 11 -C 17 alkyl or alkenyl, or mixture thereof; and Z is a polyhydroxyhydrocarbyl having a linear hydrocarbyl chain with at least 3 hydroxyls directly connected to the chain, or an alkoxylated derivative (preferably ethoxylated or propoxylated) thereof. Z preferably will be derived from
  • polyethylene, polypropylene, and polybutylene oxide condensates of alkyl phenols are suitable for use herein.
  • the polyethylene oxide condensates are preferred.
  • These compounds include the condensation products of alkyl phenols having an alkyl group containing from about 6 to about 18 carbon atoms in either a straight chain or branched chain configuration with the alkylene oxide.
  • alkyl ethoxylate condensation products of aliphatic alcohols with from about 1 to about 25 moles of ethylene oxide are suitable for use herein.
  • the alkyl chain of the aliphatic alcohol can either be straight or branched, primary or secondary, and generally contains from 6 to 22 carbon atoms.
  • Particularly preferred are the condensation products of alcohols having an alkyl group containing from 8 to 20 carbon atoms with from about 2 to about 10 moles of ethylene oxide per mole of alcohol.
  • the ethoxylated C 6 -C 18 fatty alcohols and C 6 -C 18 mixed ethoxylated/propoxylated fatty alcohols are suitable surfactants for use herein, particularly where water soluble.
  • the ethoxylated fatty alcohols are the C 10 -C 18 ethoxylated fatty alcohols with a degree of ethoxylation of from 3 to 50, most preferably these are the C 12 -C 18 ethoxylated fatty alcohols with a degree of ethoxylation from 3 to 40.
  • the mixed ethoxylated/propoxylated fatty alcohols have an alkyl chain length of from 10 to 18 carbon atoms, a degree of ethoxylation of from 3 to 30 and a degree of propoxylation of from 1 to 10.
  • the condensation products of ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol are suitable for use herein.
  • the hydrophobic portion of these compounds preferably has a molecular weight of from about 1500 to about 1800 and exhibits water insolubility.
  • Examples of compounds of this type include certain of the commercially-available PluronicTM surfactants, marketed by BASF.
  • condensation products of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylenediamine are suitable for use herein.
  • the hydrophobic moiety of these products consists of the reaction product of ethylenediamine and excess propylene oxide, and generally has a molecular weight of from about 2500 to about 3000.
  • this type of nonionic surfactant include certain of the commercially available TetronicTM compounds, marketed by BASF.
  • Suitable alkylpolysaccharides for use herein are disclosed in U.S. Patent 4,565,647, Llenado, issued January 21, 1986, having a hydrophobic group containing from about 6 to about 30 carbon atoms, preferably from about 10 to about 16 carbon atoms and a polysaccharide, e.g., a polyglycoside, hydrophilic group containing from about 1.3 to about 10, preferably from about 1.3 to about 3, most preferably from about 1.3 to about 2.7 saccharide units.
  • Any reducing saccharide containing 5 or 6 carbon atoms can be used, e.g., glucose, galactose and galactosyl moieties can be substituted for the glucosyl moieties.
  • the hydrophobic group is attached at the 2-, 3-, 4-, etc. positions thus giving a glucose or galactose as opposed to a glucoside or galactoside.
  • the intersaccharide bonds can be, e.g., between the one position of the additional saccharide units and the 2-, 3-, 4-, and/or 6- positions on the preceding saccharide units.
  • the preferred alkylpolyglycosides have the formula R 2 O(C n H 2n O)t(glycosyl) x wherein R2 is selected from the group consisting of alkyl, alkylphenyl, hydroxyalkyl, hydroxyalkylphenyl, and mixtures thereof in which the alkyl groups contain from 10 to 18, preferably from 12 to 14, carbon atoms; n is 2 or 3; t is from 0 to 10, preferably 0, and X is from 1.3 to 8, preferably from 1.3 to 3, most preferably from 1.3 to 2.7.
  • the glycosyl is preferably derived from glucose.
  • Fatty acid amide surfactants suitable for use herein are those having the formula: R 6 CON(R 7 ) 2 wherein R 6 is an alkyl group containing from 7 to 21, preferably from 9 to 17 carbon atoms and each R 7 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, and -(C 2 H 4 O) x H, where x is in the range of from 1 to 3.
  • Typical cationic surfactants for the purpose of the invention are those commonly mentioned as cationic fabric softener actives.
  • Such cationic fabric softening components include the water-insoluble quaternary-ammonium fabric softening actives, the most commonly used having been di-long alkyl chain ammonium chloride.
  • Preferred cationic softeners among these include the following:
  • cationic fabric softening components are the more environmentally-friendly materials, and rapidly biodegradable quaternary ammonium compounds which have been presented as alternatives to the traditionally used di-long chain ammonium chlorides.
  • Such quaternary ammonium compounds contain long chain alk(en)yl groups interrupted by functional groups such as carboxy groups.
  • Said materials and fabric softening compositions containing them are disclosed in numerous publications such as EP-A-0,040,562, and EP-A-0,239,910.
  • the alkyl, or alkenyl, chain T 1 , T 2 , T 3 , T 4 , T 5 must contain at least 11 carbon atoms, preferably at least 16 carbon atoms.
  • the chain may be straight or branched.
  • Tallow is a convenient and inexpensive source of long chain alkyl and alkenyl material.
  • the compounds wherein T 1 , T 2 , T 3 , T 4 , T 5 represents the mixture of long chain materials typical for tallow are particularly preferred.
  • quaternary ammonium compounds suitable for use in the aqueous fabric softening compositions herein include :
  • compounds 1-7 are examples of compounds of Formula (I); compound 8 is a compound of Formula (II). Particularly preferred is N,N-di(tallowyl-oxy-ethyl)-N,N-dimethyl ammonium chloride, where the tallow chains are at least partially unsaturated.
  • the level of unsaturation of the tallow chain can be measured by the Iodine Value (IV) of the corresponding fatty acid, which in the present case should preferably be in the range of from 5 to 100 with two categories of compounds being distinguished, having a IV below or above 25.
  • the anion is merely present as a counterion of the positively charged quaternary ammonium compounds.
  • the nature of the counterion is not critical at all to the practice of the present invention. The scope of this invention is not considered limited to any particular anion.
  • amine precursors thereof is meant the secondary or tertiary amines corresponding to the above quaternary ammonium compounds, said amines being substantially protonated in the present compositions due to the pH values.
  • cationic surfactants may also be used in addition to or in alternative to the above mentioned cationic surfactants having fabric softening properties.
  • This include the monoalkyl ammonium halide such as trimethyl alkyl ammonium halide (R'-N + (Me) 3 X - ) such as C16 trimethyl ammonium bromide or C14 trimethyl ammonium bromide; N-alkyl N,N-dimethyl-N(2-hydroxyethyl) ammonium ( R'-N + (Me) 2 CH 2 CH 2 OH X - ) and mixtures thereof, and wherein R' is an alkyl chain having at least 8 carbons and X - is a conteranion as defined herein before.
  • R' is an alkyl chain having at least 8 carbons and X - is a conteranion as defined herein before.
  • surfactants are the cationic surfactants, most preferably the cationic surfactants mentioned above as having fabric softening properties.
  • Typical levels of said surfactants are from 0.1% to 80% by weight of the compositions.
  • Acidic materials are essential to the stability of the composition of the invention. Acidity may be provided from the above mentioned betaine ester, especially with those selected from N-dodecylglycine geranyl ester hydrobromide or hydrochloride; N,N-dioctylglycine geranyl ester hydrobromide or hydrochloride; N,N-didodecylglycine geranyl ester hydrobromide or hydrochloride; N-butyl-N-(2-geranyloxy-2-oxoethyl)glycine geranyl ester hydrobromide or hydrochloride; N-dodecyl-N-(2-geranyloxy-2-oxoethyl)glycine geranyl ester hydrobromide or hydrochloride; N,N-bis(2-geranyloxy-2-oxoethyl)glycine geranyl ester hydrobromide or hydrochloride; and/or the
  • Suitable conventional acidic materials include the bronstead acids as well as the fatty acids.
  • suitable acids include the inorganic mineral acids, carboxylic acids, in particular the low molecular weight (C 1 -C 5 ) carboxylic acids, and alkyl sulfonic acids and mixtures thereof.
  • Suitable inorganic acids include HCl, H 2 SO 4 , HNO 3 and H 3 PO 4 .
  • Suitable organic acids include formic, acetic, methylsulfonic and ethylsulfonic acid.
  • Preferred acids are hydrochloric, phopshoric, formic and methylsulfonic acid.
  • the amount of acidic material should be such that the pH of the composition is less than 7, preferably from 2.0 to 5.5.
  • optimum hydrolytic stability of these compositions will be obtained when the pH of the compositions, measured in the neat compositions at 20°C, is in the range of from 2.0 to 4.5.
  • the amount of acid is from 1% to 30% by weight, preferably 2% to 30%, most preferably 3% to 15% by weight of the cationic surfactant.
  • composition will comprise up to 5% by weight, more preferably from 0.1% to 1.5% by weight of additional perfume.
  • perfumes are those odorous materials that deposit on fabrics or surfaces during the laundry or cleaning process and are detectable by people with normal olfactory sensitivity.
  • perfume ingredients along with their odour corrector and their physical and chemical properties are given in "Perfume and Flavor chemicals (aroma chemicals)", Stephen Arctender, Vols. I and II, Aurthor, Montclair, H.J. and the Merck Index, 8th Edition, Merck & Co., Inc. Rahway, N.J.
  • Perfume components and compositions can also be found in the art, e.g. US Patent Nos. 4,145,184, 4,152,272, 4,209,417 or 4,515,705.
  • perfume use includes materials such as aldehydes, ketones, esters and the like. More commonly, naturally occurring plant and animal oils and exudates comprising complex mixtures of various chemical components are known for use as perfume, and such materials can be used herein.
  • Typical perfumes can comprise e.g. woody/earthy bases containing exotic materials such as sandalwood oil, civet and patchouli oil.
  • the perfume also can be of a light floral fragrance e.g. rose or violet extract.
  • the perfume can be formulated to provide desirable fruity odours e.g. lime, lemon or orange.
  • perfume ingredients and compositions are anetole, benzaldehyde, benzyl acetate, benzyl alcohol, benzyl formate, isobornyl acetate, camphene, cis-citral (neral), citronellal, citronellol, citronellyl acetate, paracymene, decanal, dihydrolinalool, dihydromyrcenol, dimethyl phenyl carbinol, eucalyptol, geranial, geraniol, geranyl acetate, geranyl nitrile, cis-3-hexenyl acetate, hydroxycitronellal, d-limonene, linalool, linalool oxide, linalyl acetate, linalyl propionate, methyl anthranilate, alpha-methyl ionone, methyl nonyl acetaldehyde, methyl pheny
  • compositions according to the present invention are suitable for use where acidic products and surfactants, preferably a cationic surfactant are present.
  • acidic products include fabric softeners, hard surface cleaners, bathroom cleaners, shower gels, deodorants, bars, shampoos, conditioners.
  • the cationic surfactants which also act as fabric softener will preferably be present, depending on the composition execution, in amount of 1% to 8% by weight where the composition is in diluted form or in amount of 8% to 80%, more preferably 10% to 50%, most preferably 15% to 35% by weight where the composition is in concentrated form.
  • the fabric softener composition may also optionally comprise conventional softening ingredients such as nonionic extenders, surfactants concentration aids, electrolyte concentration aids, stabilisers, such as well known antioxidants and reductive agents, Soil Release Polymers, emulsifiers, bacteriocides, colorants, perfumes, preservatives, optical brighteners, anti ionisation agents, antifoam agents and enzymes.
  • conventional softening ingredients such as nonionic extenders, surfactants concentration aids, electrolyte concentration aids, stabilisers, such as well known antioxidants and reductive agents, Soil Release Polymers, emulsifiers, bacteriocides, colorants, perfumes, preservatives, optical brighteners, anti ionisation agents, antifoam agents and enzymes.
  • Also provided herein by the present invention is a process for preparing a composition as described herein before, which comprises the steps of
  • the molten mixture of step a) will be dispersed in a waterseat of step b) above the Krafft temperature of the surfactant.
  • the waterseat may optionally contain additives such as polyethylene glycol or biocide. Acids may be added in step a) or directly to the waterseat of step b). Optional components such as dyes, perfumes if present will be added either before step e) once the resulting dispersion is made or after step e).
  • the temperature of the molten mixture is above the Krafft temperature of the surfactant.
  • Krafft temperature is meant the temperature at which the solubility of the surfactant becomes equal to the critical micelle concentration (CMC), the CMC being defined in M.J ROSEN, Surfactants and interfacial phenomena, 1988, p.215.
  • the amount of shear should be sufficient to properly disperse the surfactant. Proper dispersion can be verified by controlling the particle size of the resulting dispersion, by e.g microscopy or light scattering techniques. The particle size should preferably be below 50 ⁇ m.
  • the cooling step it is preferred for optimal storage results to cool the resulting mixture below the Krafft temperature of the surfactant before the product is stored.
  • the surfactant used is a cationic surfactant.
  • This type of synthesis can also be conveniently applied to the synthesis of N,N-dioctylglycine phenoxanyl ester; N,N-dioctylglycine cis-3-hexenyl ester as well as for N,N-didodecylglycine phenoxanyl ester, N,N-didodecylglycine cis-3-hexenyl ester and N,N-didodecylglycine geranyl ester with the exception that for the three last one N,N-dioctylglycine methyl ester is used in the synthesis instead of N,N-dioctylglycine methyl ester.
  • Linalyl chloroacetate (5.77 g, 25 mmol, 1 eq), in toluene (50 ml), was slowly added to didodecylamine (10 g, 28.3 mmol, 1.13 eq) and sodium carbonate (5.3 g, 0.05 mol, 2 eq), in toluene (50 ml).
  • the reaction mixture was stirred at 60°C for two weeks after which the reaction seemed completed by 1H NMR.
  • the sodium carbonate was filtered off, the filtrate was concentrated under vacuum and diethyl ether (200 ml) was added before storage of the solution at 4°C for 12 hours. Then, the solution was filtered and removal of ether under vacuum yielded to the expected N,N-didodecylglycine linalyl ester as a yellow oil.
  • This type of synthesis can also be conveniently applied to the synthesis of N,N-dioctylglycine esters and N,N-didodecylglycine esters of unhindered alcohols.
  • the N,N-dioctylglycine esters hydrochloride or hydrobromide and the N,N-didodecylglycine esters hydrochloride or hydrobromide can be easily obtained by dissolving N,N-dioctylglycine esters or N,N-didodecylglycine esters in an organic solvant such as methanol, ethanol, isopropanol, petroleum ether, diethyl ether, toluene and adding at least a stoechiometric amount of mineral acid in water or in an organic solvant (such as HCl in isopropanol).
  • an organic solvant such as methanol, ethanol, isopropanol, petroleum ether, diethyl ether, toluene
  • Linalyl chloroacetate (55.04 g, 200 mmol, 2 eq), in acetonitrile (75 ml), was slowly added to dodecylamine (24.2 ml, 100 mmol, 1 eq) and sodium carbonate (42.4 g, 0.4 mol, 4eq), in acetonitrile (50 ml).
  • the reaction mixture was stirred at 50°C for two weeks after which the reaction seemed completed by 1H NMR.
  • the sodium carbonate was filtered off, the filtrate was concentrated under vacuum and diethyl ether (200 ml) was added before storage of the solution at 4°C for 12 hours.
  • This type of synthesis can also be conveniently applied to the chloroacetate or bromoacetate of unhindered alcohols such as geraniol, phenoxanol, cis-3-hexenol.
  • the hydrochloride or hydrobromide salts can be obtained by dissolving for example N-butyl-N-(2-geranyloxy-2-oxoethyl)glycine geranyl ester in an organic solvant such as methanol, ethanol, isopropanol, petroleum ether, diethyl ether, toluene and adding at least a stoechiometric amount of mineral acid (HCl or HBr) in water or an organic solvant (such as HCl in isopropanol).
  • an organic solvant such as methanol, ethanol, isopropanol, petroleum ether, diethyl ether, toluene
  • This type of synthesis can also be conveniently applied to the synthesis of N,N-bis(2-phenoxanyloxy-2-oxoethyl)glycine phenoxanyl ester and N,N-bis(2-cis-3-hexenyloxy-2-oxoethyl)glycine cis-3-hexenyl ester.
  • Linalyl chloroacetate (82.56 g, 300 mmol, 3 eq), in acetonitrile (100 ml), was slowly added to ammonia (50 ml of 2N solution in 2-propanol, 100 mmol, 1 eq) and sodium carbonate (63.6 g, 0.6 mol, 6 eq), in acetonitrile (350 ml).
  • the reaction mixture was stirred at 50°C for two weeks after which the reaction seemed completed by 1H NMR.
  • the sodium carbonate was filtered off, the filtrate was concentrated under vacuum and diethyl ether (200 ml) was added before storage of the solution at 4°C for 12 hours. Then, the solution was filtered and removal of ether under vacuum yielded to the expected N,N-bis(2-linalyloxy-2-oxoethyl)glycine linalyl ester as a brown oil.
  • This type of synthesis can also be conveniently applied to the synthesis of chloroacetate or bromoacetate of unhindered alcohols such as geraniol, phenoxanol, cis-3-hexenol.
  • the hydrochloride or hydrobromide salts can be obtained by dissolving for example N,N-bis(2-linalyloxy-2-oxoethyl)glycine linalyl ester in an organic solvant such as methanol, ethanol, isopropanol, petroleum ether, diethyl ether, toluene and adding at least a stoechiometric amount of mineral acid (HCl or HBr) in water or an organic solvant (such as HCl in isopropanol).
  • an organic solvant such as methanol, ethanol, isopropanol, petroleum ether, diethyl ether, toluene
  • the following hard surface cleaner compositions according to the present invention were prepared by mixing the listed ingredients F G H I CTAB 3.2 - - - Cetrimide - 4.2 - - C8-10 dimethyl amine oxide - - - 4.40 Lutensol® AO 30 - - 0.75 3.0 Dobanol® 91-10 - - 2.60 - Dobanol® 23-6.5 - - 0.90 - Dobanol® 23-3 - - 1.75 - Maleic acid 8.0 8.6 - - Citric acid - - - 5.50 Alkyl sulphate - - - 4.0 Ammonia (as NH 4 OH) - - - 0.40 Propane diol - - - 1.30 H 2 O 2 - - 7.0 - H 2 SO 4 up to pH - - 4.0 - DGGE 1.0 0.5 1.0 0.6 water and miscellaneous to balance pH as is 1.0 0.9 4.0 3.2

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EP96302291A 1996-04-01 1996-04-01 Composés bétaine ester des aclcools actifs Withdrawn EP0799885A1 (fr)

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EP96302291A EP0799885A1 (fr) 1996-04-01 1996-04-01 Composés bétaine ester des aclcools actifs
AU25908/97A AU2590897A (en) 1996-04-01 1997-03-27 Betaine ester compounds of active alcohols
BR9710416A BR9710416A (pt) 1996-04-01 1997-03-27 Compostos de ïÕïster de betaina de alcoÄis ativos
CN97195159A CN1220693A (zh) 1996-04-01 1997-03-27 活性醇的甜菜碱酯类化合物
CA002250837A CA2250837C (fr) 1996-04-01 1997-03-27 Composes d'ester de betaine d'alcools actifs
PCT/US1997/004959 WO1997036978A1 (fr) 1996-04-01 1997-03-27 Composes d'ester de betaine d'alcools actifs
US09/155,779 US5958870A (en) 1996-04-01 1997-03-27 Betaine ester compounds of active alcohols
JP53540697A JP3770916B2 (ja) 1996-04-01 1997-03-27 活性アルコールのベタインエステル組成物
ARP970101299A AR008583A1 (es) 1996-04-01 1997-04-01 Composicion acida acuosa que contiene un ester de betaina de un alcohol activo y procedimiento para prerarar dicha composicion
ZA9702775A ZA972775B (en) 1996-04-01 1997-04-01 Betaine ester compounds of active alcohols.

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WO2001027234A1 (fr) * 1999-10-08 2001-04-19 Henkel Kommanditgesellschaft Auf Aktien Constituant de detergent a liberation de parfum a double controle
WO2002077074A1 (fr) 2001-03-27 2002-10-03 Firmenich Sa Composes servant a effectuer la liberation controlee de composes actifs
DE10132174A1 (de) * 2001-07-03 2003-03-27 Goldschmidt Ag Th Neue Betainester
WO2003038022A1 (fr) * 2001-10-27 2003-05-08 Henkel Kommanditgesellschaft Auf Aktien Agent a base d'esters de betaine
WO2003089558A1 (fr) * 2002-04-20 2003-10-30 Goldschmidt Rewo Gmbh & Co. Kg Compositions d'adoucissant textile contenant des derives d'ester de betaine et procede d'amelioration du pouvoir lavant de lessives
US6677297B2 (en) 1999-10-18 2004-01-13 Firmenich Sa Esters comprising a secondary carbamoyl function and their use as odorant alcohol precursors
WO2004020729A1 (fr) * 2002-08-27 2004-03-11 Ciba Specialty Chemicals Holding Inc. Procede d'administration de substances actives au plan biologique
US6897263B2 (en) 2001-07-03 2005-05-24 Goldschmidt Ag Betaine esters
US7229958B2 (en) 2005-06-09 2007-06-12 Degussa Ag Fragrance alcohol-releasing polysiloxane
DE102007012909A1 (de) 2007-03-19 2008-09-25 Momentive Performance Materials Gmbh Mit Duftstoffen modifizierte, reaktive Polyorganosiloxane
DE102007012910A1 (de) 2007-03-19 2008-09-25 Momentive Performance Materials Gmbh Mit Duftstoffen modifizierte, verzweigte Polyorganosiloxane
EP2008637A1 (fr) 2007-06-18 2008-12-31 Firmenich Sa Compositions d'annihilation malodorantes et leur procédé d'utilisation
DE102007037147A1 (de) 2007-08-07 2009-02-12 Henkel Ag & Co. Kgaa Duftkomposite mit verbesserter Duftfreisetzung
US8022030B2 (en) 2006-10-10 2011-09-20 Firmenich Sa Polymer conjugates for a controlled release of active molecules
US8399499B2 (en) 2007-05-22 2013-03-19 Firmenich Sa 3- to 7-membered 1,3-diaza-4-OXO-heterocyclic derivatives capable of releasing active aldehydes or ketones
WO2013139766A1 (fr) 2012-03-20 2013-09-26 Firmenich Sa Composés pour une libération contrôlée de molécules parfumantes actives
WO2014029695A1 (fr) 2012-08-21 2014-02-27 Firmenich Sa Procédé d'amélioration des performances de fragrances encapsulées
WO2015032885A1 (fr) 2013-09-09 2015-03-12 Firmenich Sa Dérivés de thioéther comme précurseurs pour une libération contrôlée de molécules actives
WO2016091815A1 (fr) 2014-12-10 2016-06-16 Firmenich Sa Polysiloxanes en tant que systèmes de libération de parfum en parfumerie fine
US9765282B2 (en) 2013-06-19 2017-09-19 Firmenich Sa Polysiloxane conjugates as fragrance delivery systems
WO2018002214A1 (fr) 2016-06-30 2018-01-04 Firmenich Sa Microcapsules à noyau et enveloppe composite
US10034819B2 (en) 2012-09-24 2018-07-31 Firmenich Sa Multilayered core/shell microcapsules
US10323127B2 (en) 2015-02-17 2019-06-18 Firmenich Sa Poly(aspartic acid) derived co-polymers for a controlled release of perfuming ingredients
US10377965B2 (en) 2015-01-21 2019-08-13 Firmenich Sa Photolabile acetal and ketal compounds for the controlled release of active volatile carbonyl compounds
WO2019243369A1 (fr) 2018-06-21 2019-12-26 Firmenich Sa Composés destinés à fournir une odeur de fraise de longue durée
WO2020127708A1 (fr) 2018-12-20 2020-06-25 Firmenich Sa Pro-parfum d'alkylénoléther
WO2021023670A1 (fr) 2019-08-08 2021-02-11 Firmenich Sa Composés destinés à fournir une odeur de menthe de longue durée
WO2021110680A1 (fr) 2019-12-03 2021-06-10 Firmenich Sa Pro-parfum d'énoléther
WO2021122997A1 (fr) 2019-12-19 2021-06-24 Firmenich Sa Composés destinés à fournir une odeur florale et fruitée de longue durée
WO2021123144A1 (fr) 2019-12-20 2021-06-24 Firmenich Sa Compositions de proparfum
WO2021209396A1 (fr) 2020-04-14 2021-10-21 Firmenich Sa Composés destinés à fournir une odeur de longue durée
WO2021250164A1 (fr) 2020-06-12 2021-12-16 Firmenich Sa Pro-parfum d'éther énolique
WO2022084437A1 (fr) 2020-10-21 2022-04-28 Firmenich Sa Compositions conférant une fraîcheur améliorée
WO2023067063A1 (fr) 2021-10-20 2023-04-27 Firmenich Sa Compositions de parfum améliorées comprenant des composés pro-parfum contenant du soufre
WO2023067072A1 (fr) 2021-10-20 2023-04-27 Firmenich Sa Compositions de parfum améliorées comprenant des composés de précurseur de parfum contenant du soufre
WO2023078909A1 (fr) 2021-11-03 2023-05-11 Firmenich Sa Acétals et cétals cycliques pour la libération induite par la lumière d'aldéhydes et de cétones actifs
WO2023111006A1 (fr) 2021-12-14 2023-06-22 Firmenich Sa Pro-parfum d'éther énolique

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US20080139378A1 (en) * 2006-12-07 2008-06-12 Degussa Ag Urine-absorbing composition with fragrance release upon use
US9585826B2 (en) * 2012-11-07 2017-03-07 Kimberly-Clark Worldwide, Inc. Triggerable compositions for two-stage, controlled release of active chemistry
CN108342263B (zh) * 2017-01-25 2022-01-28 花王株式会社 液体清洁剂组合物
CN108387559B (zh) * 2018-01-15 2023-05-12 南方医科大学 一种表面活性剂临界胶束浓度试纸及其制备方法

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EP0192145A2 (fr) * 1985-02-15 1986-08-27 Hoechst Aktiengesellschaft Ester quaternaire d'alcoylamidobétaine, préparation et utilisation comme agent assouplissant pour textile
DE3527974A1 (de) * 1985-08-03 1987-02-12 Wella Ag Saures haarpflegemittel
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Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001027234A1 (fr) * 1999-10-08 2001-04-19 Henkel Kommanditgesellschaft Auf Aktien Constituant de detergent a liberation de parfum a double controle
US6677297B2 (en) 1999-10-18 2004-01-13 Firmenich Sa Esters comprising a secondary carbamoyl function and their use as odorant alcohol precursors
WO2002077074A1 (fr) 2001-03-27 2002-10-03 Firmenich Sa Composes servant a effectuer la liberation controlee de composes actifs
DE10132174A1 (de) * 2001-07-03 2003-03-27 Goldschmidt Ag Th Neue Betainester
US6897263B2 (en) 2001-07-03 2005-05-24 Goldschmidt Ag Betaine esters
WO2003038022A1 (fr) * 2001-10-27 2003-05-08 Henkel Kommanditgesellschaft Auf Aktien Agent a base d'esters de betaine
WO2003089558A1 (fr) * 2002-04-20 2003-10-30 Goldschmidt Rewo Gmbh & Co. Kg Compositions d'adoucissant textile contenant des derives d'ester de betaine et procede d'amelioration du pouvoir lavant de lessives
US7056878B2 (en) 2002-04-20 2006-06-06 Goldschmidt Rewo Gmbh & Co. Kg Rinse cycle fabric softener formulations containing betaine ester derivatives and method for improving the washing performance of detergents
WO2004020729A1 (fr) * 2002-08-27 2004-03-11 Ciba Specialty Chemicals Holding Inc. Procede d'administration de substances actives au plan biologique
US7229958B2 (en) 2005-06-09 2007-06-12 Degussa Ag Fragrance alcohol-releasing polysiloxane
US8022030B2 (en) 2006-10-10 2011-09-20 Firmenich Sa Polymer conjugates for a controlled release of active molecules
DE102007012909A1 (de) 2007-03-19 2008-09-25 Momentive Performance Materials Gmbh Mit Duftstoffen modifizierte, reaktive Polyorganosiloxane
DE102007012910A1 (de) 2007-03-19 2008-09-25 Momentive Performance Materials Gmbh Mit Duftstoffen modifizierte, verzweigte Polyorganosiloxane
US8399499B2 (en) 2007-05-22 2013-03-19 Firmenich Sa 3- to 7-membered 1,3-diaza-4-OXO-heterocyclic derivatives capable of releasing active aldehydes or ketones
EP2008637A1 (fr) 2007-06-18 2008-12-31 Firmenich Sa Compositions d'annihilation malodorantes et leur procédé d'utilisation
US8772354B2 (en) 2007-06-18 2014-07-08 Firmenich Sa Malodor counteracting compositions and method for their use
DE102007037147A1 (de) 2007-08-07 2009-02-12 Henkel Ag & Co. Kgaa Duftkomposite mit verbesserter Duftfreisetzung
WO2013139766A1 (fr) 2012-03-20 2013-09-26 Firmenich Sa Composés pour une libération contrôlée de molécules parfumantes actives
US11155772B2 (en) 2012-03-20 2021-10-26 Firmenich Sa Compounds for a controlled release of active perfuming molecules
WO2014029695A1 (fr) 2012-08-21 2014-02-27 Firmenich Sa Procédé d'amélioration des performances de fragrances encapsulées
US9487733B2 (en) 2012-08-21 2016-11-08 Firmenich Sa Method to improve the performance of encapsulated fragrances
US10034819B2 (en) 2012-09-24 2018-07-31 Firmenich Sa Multilayered core/shell microcapsules
US9765282B2 (en) 2013-06-19 2017-09-19 Firmenich Sa Polysiloxane conjugates as fragrance delivery systems
US9758749B2 (en) 2013-09-09 2017-09-12 Firmenich Sa Thioether derivatives as precursors for a controlled release of active molecules
WO2015032885A1 (fr) 2013-09-09 2015-03-12 Firmenich Sa Dérivés de thioéther comme précurseurs pour une libération contrôlée de molécules actives
US9902920B2 (en) 2014-12-10 2018-02-27 Firmenich Sa Polysiloxanes as fragrance delivery systems in fine perfumery
WO2016091815A1 (fr) 2014-12-10 2016-06-16 Firmenich Sa Polysiloxanes en tant que systèmes de libération de parfum en parfumerie fine
US10377965B2 (en) 2015-01-21 2019-08-13 Firmenich Sa Photolabile acetal and ketal compounds for the controlled release of active volatile carbonyl compounds
US10508252B2 (en) 2015-01-21 2019-12-17 Firmenich Sa Photolabile acetal and ketal compounds for the controlled release of active volatile carbonyl compounds
US10323127B2 (en) 2015-02-17 2019-06-18 Firmenich Sa Poly(aspartic acid) derived co-polymers for a controlled release of perfuming ingredients
WO2018002214A1 (fr) 2016-06-30 2018-01-04 Firmenich Sa Microcapsules à noyau et enveloppe composite
US11179302B2 (en) 2016-06-30 2021-11-23 Firmenich Sa Core-composite shell microcapsules
EP4272861A2 (fr) 2016-06-30 2023-11-08 Firmenich SA Un produit de consommation comprenant des microcapsules avec enveloppe à noyau composite
WO2019243369A1 (fr) 2018-06-21 2019-12-26 Firmenich Sa Composés destinés à fournir une odeur de fraise de longue durée
WO2020127708A1 (fr) 2018-12-20 2020-06-25 Firmenich Sa Pro-parfum d'alkylénoléther
WO2021023670A1 (fr) 2019-08-08 2021-02-11 Firmenich Sa Composés destinés à fournir une odeur de menthe de longue durée
WO2021110680A1 (fr) 2019-12-03 2021-06-10 Firmenich Sa Pro-parfum d'énoléther
WO2021122997A1 (fr) 2019-12-19 2021-06-24 Firmenich Sa Composés destinés à fournir une odeur florale et fruitée de longue durée
WO2021123144A1 (fr) 2019-12-20 2021-06-24 Firmenich Sa Compositions de proparfum
WO2021209396A1 (fr) 2020-04-14 2021-10-21 Firmenich Sa Composés destinés à fournir une odeur de longue durée
WO2021250164A1 (fr) 2020-06-12 2021-12-16 Firmenich Sa Pro-parfum d'éther énolique
WO2022084437A1 (fr) 2020-10-21 2022-04-28 Firmenich Sa Compositions conférant une fraîcheur améliorée
WO2023067063A1 (fr) 2021-10-20 2023-04-27 Firmenich Sa Compositions de parfum améliorées comprenant des composés pro-parfum contenant du soufre
WO2023067072A1 (fr) 2021-10-20 2023-04-27 Firmenich Sa Compositions de parfum améliorées comprenant des composés de précurseur de parfum contenant du soufre
WO2023078909A1 (fr) 2021-11-03 2023-05-11 Firmenich Sa Acétals et cétals cycliques pour la libération induite par la lumière d'aldéhydes et de cétones actifs
WO2023111006A1 (fr) 2021-12-14 2023-06-22 Firmenich Sa Pro-parfum d'éther énolique

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AR008583A1 (es) 2000-02-09
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JP2000509107A (ja) 2000-07-18
AU2590897A (en) 1997-10-22
BR9710416A (pt) 1999-08-17
WO1997036978A1 (fr) 1997-10-09
JP3770916B2 (ja) 2006-04-26
CA2250837A1 (fr) 1997-10-09
CA2250837C (fr) 2002-02-19

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