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WO1997036978A1 - Composes d'ester de betaine d'alcools actifs - Google Patents

Composes d'ester de betaine d'alcools actifs Download PDF

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Publication number
WO1997036978A1
WO1997036978A1 PCT/US1997/004959 US9704959W WO9736978A1 WO 1997036978 A1 WO1997036978 A1 WO 1997036978A1 US 9704959 W US9704959 W US 9704959W WO 9736978 A1 WO9736978 A1 WO 9736978A1
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WO
WIPO (PCT)
Prior art keywords
ester
hγdrochloride
hγdrobromide
composition according
aqueous acidic
Prior art date
Application number
PCT/US1997/004959
Other languages
English (en)
Inventor
Marc Johan Declercq
Hugo Jean-Marie Demeyere
Arnaud Pierre Struillou
Original Assignee
The Procter & Gamble Company
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 The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP53540697A priority Critical patent/JP3770916B2/ja
Priority to CA002250837A priority patent/CA2250837C/fr
Priority to BR9710416A priority patent/BR9710416A/pt
Priority to AU25908/97A priority patent/AU2590897A/en
Priority to US09/155,779 priority patent/US5958870A/en
Publication of WO1997036978A1 publication Critical patent/WO1997036978A1/fr

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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.
  • 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 10 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 1 5 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.
  • 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 30 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” 35 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.
  • 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.
  • 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 a) a betaine ester of an active alcohol which, at a concentration of from 0.01 % to 10% by weight, is predominantly in the form of micelles, and/or is capable of being incorporated into micelles, and b) a surfactant, said composition comprising an acidic material in sufficient amount to render the pH of the composition of less than 7.
  • the betaine ester is a hydrophobic betaine ester of formula:
  • , R2, R3 independently, is selected from hydrogen, alkyl group, aryl group, and
  • 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, wherein R4 is an alkyl group having from 7 to 19 carbon atoms, wherein each R' -
  • n2 is an integer lying in the range of 0 to 20
  • n3 independently, is an integer lying in the range from 1 to 3
  • each R independently, is an organic chain of an active alcohol.
  • a process for preparing said acidic composition comprises the following steps: - mixing the surfactant and optional components, if any, at a temperature above the melting point of the surfactant , preparing a waterseat, dispersing the mixture prepared above in the waterseat, and optionally, cooling the resulting dispersion.
  • Protection of the betaine ester occurs by incorporation of said betaine ester with the molten surfactant, or prior to dispersion of the molten surfactant in a waterseat, or with the surfactant dispersion while the dispersion is at a temperature above the Krafft point of the surfactant or combination of any of the above.
  • 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.
  • 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:
  • each R-j , R2, R3 independently, is selected from hydrogen, alkyl group, aryl group,
  • 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, wherein R4 is an alkyl group having from 7 to 1 9 carbon atoms, wherein each R' -
  • each n2 independently, 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-j , R2, R3 are each, independently selected from H, alkyl chain having from 1 to 20 carbon atoms, with the proviso that at least one of R-
  • , 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,
  • 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 geranyloxycarbony!-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- oxoethyDglycine geranyl ester hydrobromide or hydrochloride N-butyl-N-(2- citronellyloxy-2-oxoethyl)glycine citronellyl ester hydrobromide or hydrochloride
  • N-butyl-N-(2-dihydromyrcenyloxy-2- oxoethyDglycine dihydromyrcenyl ester hydrobromide or hydrochloride N-butyl-N-(2-geranyloxy-2- oxoethyDglycine geranyl ester hydrobromide or hydrochloride.
  • N-dodecyl-N-(2-geranyloxy-2- oxoethyDglycine geranyl ester hydrobromide or hydrochloride N-dodecyl-N- (2-citronellyloxy-2-oxoethyl)glycine citronellyl ester hydrobromide or hydrochloride
  • N-dodecyl-N-(2-dihydromyrcenyloxy-2- oxoethyUglycine dihydromyrcenyl ester hydrobromide or hydrochloride N-dodecyl-N-(2-geranyloxy-2- oxoethyDglycine geranyl ester hydrobromide or hydrochloride.
  • N,N-bis(2-geranyloxy-2- oxoethyDglycine geranyl ester hydrobromide or hydrochloride N,N-bis(2- citronellyloxy-2-oxoethyl)glycine citronellyl ester hydrobromide or hydrochloride; N,N-bis(2-linalyloxy-2-oxoethyl)glycine linalyl ester hydrobromide or hydrochloride; N,N-bis(2-dihydromyrcenyloxy-2- oxoethyDglycine dihydromyrcenyl 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 - j-C- j g monoesters) diesters of sulfosuccinate (especially saturated and unsaturated C ⁇ -C 1 4 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 C5-C1 7 acyl-N-(C-
  • Alkyl ethoxysulfate surfactants are preferably selected from the group consisting of the C ⁇ -C-i g 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 C6-C 1 8 a,k y' 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 C5-C20 linear alkylbenzene sulfonates, alkyl ester sulfonates, C6-C22 primary or secondary alkane sulfonates, C6-C24 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(CH2CH2 ⁇ ) x CH2COO-M + wherein R is a CQ to C-
  • the preferred alkyl ethoxy carboxylates are those where R is a C12
  • Alkyl polyethoxy polycarboxylate surfactants suitable for use herein include those having the formula RO-(CHR-
  • 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 1 1 -1 5 total carbon atoms, although slightly more (e.g., up to 1 6) can be tolerated, e.g. p-octyl benzoic acid.
  • a highly preferred class of secondary soaps comprises the secondary carboxyl materials of the formula R 3 CH(R )COOM, wherein R 3 is CH3(CH2>x and R 4 is CH3 ⁇ CH2)y, wherein y can be O or an integer from 1 to 4, x is an integer from 4 to 10 and the sum of (x + y) is 6-10, preferably 7-9, most preferably 8.
  • Another preferred class of secondary soaps comprises those carboxyl compounds wherein the carboxyl substituent is on a ring hydrocarbyl unit, i.e., secondary soaps of the formula R5-R6-COO , wherein R ⁇ is C ⁇ -C ⁇ O, preferably C ⁇ -C ⁇ , alkyl or alkenyl and R ⁇ is a ring structure, such as benzene, cyclopentane and cyclohexane. (Note: R ⁇ can be in the ortho, meta or para position relative to the carboxyl on the ring.)
  • Still another preferred class of secondary soaps comprises secondary carboxyl compounds of the formula
  • 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-butyl-1 -octanoic acid and 2-pentyl-1 -heptanoic acid.
  • alkali metal sarcosinates of formula R-CON (R1 ) CH2 COOM, wherein R is a C5-C17 linear or branched alkyl or alkenyl group, R 1 is a C1 - 4 alkyl group and M is an alkali metal ion.
  • R is a C5-C17 linear or branched alkyl or alkenyl group
  • R 1 is a C1 - 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, C1 -C4 hydrocarbyl, 2- hydroxy ethyl, 2-hydroxy propyl, or a mixture thereof, preferable C1 -C4 alkyl, more preferably Ci or C2 alkyl, most preferably C-
  • Z preferably
  • the 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 1 8 carbon atoms in either a straight chain or branched chain configuration with the alkylene oxide.
  • the 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.
  • the ethoxylated C ⁇ -C-i g fatty alcohols and C -C-i g mixed ethoxylated/propoxylated fatty alcohols are suitable surfactants for use herein, particularly where water soluble.
  • the ethoxylated fatty alcohols are the C10-C18 ethoxylated fatty alcohols with a degree of ethoxylation of from 3 to 50, most preferably these are the C1 2-C18 ethoxylated fatty alcohols with a degree of ethoxylation from 3 to 40.
  • the mixed ethoxylated/propoxylated fatty alcohols have an alkyl chain Iength 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 1 500 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 alkyipolysaccharides for use herein are disclosed in U.S. Patent 4,565,647, Llenado, issued January 21 , 1 986, having a hydrophobic group containing from about 6 to about 30 carbon atoms, preferably from about 10 to about 1 6 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
  • 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 1 2 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: R6C0N(R7)2 wherein R ⁇ is an alkyl group containing from 7 to 21 , preferably from 9 to 1 7 carbon atoms and each is selected from the group consisting of hydrogen, C1 -C4 alkyl, C1 -C4 hydroxyalkyl, and - (C2H4 ⁇ ) 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.
  • 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:
  • DTDMAC ditallow dimethylammonium chloride
  • DTDMAC ditallow dimethylammonium chloride
  • 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 quaternary ammonium compounds and amine precursors herein have the formula (I) or (II), below :
  • Q is selected from -O-C(O)-, -C(O)-O-, -O-C(O)-O-, -NR -C(O)-, -
  • R is (CH 2 ) n -Q-T 2 or T 3 ;
  • R 2 is (CH 2 )m-Q-T 4 or T ⁇ or R 3 ;
  • R 3 is C 1 -C4 alkyl or C1 -C4 hydroxyalkyl or H;
  • R 4 is H or C1 -C4 alkyl or C1 -C4 hydroxyalkyl
  • T1 , T 2 , T 3 , T 4 , T ⁇ are independently Ci 1 -C22 a ' or alkenyl; n and m are integers from 1 to 4; and
  • X ' is a softener-compatible anion.
  • Non-limiting examples of softener-compatible anions include chloride or methyl sulfate.
  • the alkyl, or alkenyl, chain T 1 , T 2 , T 3 , T 4 , T ⁇ must contain at least 1 1 carbon atoms, preferabl ⁇ at least 1 6 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 " l , T 2 , T 3 , T 4 , T ⁇ 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 :
  • N,N,N-tri(tallowyl-oxy-ethyl)-N-methyl ammonium chloride 6) N,N,N-tri(tallowyl-oxy-ethyl)-N-methyl ammonium chloride; 7) N-(2-tallowyl-oxy-2-oxo-ethyl)-N-(tallowyl-N,N-dimethyl-ammonium chloride; and 8) 1 ,2-ditallowyl-oxy-3-trimethylammoniopropane chloride; and mixtures of any of the above materials.
  • 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 C1 6 trimethyl ammonium bromide or C14 trimethyl ammonium bromide; N-alkyl N,N-dimethyl-N(2- hydroxyethyl) ammonium ( R'-N + (Me)2CH2CH2OH 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.
  • 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- oxoethyDglycine 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 (C1 -C5) carboxylic acids, and alkyl sulfonic acids and mixtures thereof.
  • Suitable inorganic acids include HCl, H2SO4, HNO3 and H3PO4.
  • 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 1 5% 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, 1 52,272, 4,209,41 7 or 4,51 5,705.
  • 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, iso ⁇ bornyl acetate, camphene, cis-citral (neral), citronellal, citronellol, citronellyl acetate, paracymene, decanal, dih ⁇ drolinalool, 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, meth ⁇ l anthranilate, alpha-methyl ionone, meth ⁇ l non ⁇ l acetaldeh
  • compositions according to the present invention are suitable for use where acidic products and surfactants, preferabl ⁇ 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 preferabl ⁇ be present, depending on the composition execution, in amount of 1 % to 8% b ⁇ weight where the composition is in diluted form or in amount of 8% to 80%, more preferabl ⁇ 1 0% to 50%, most preferabl ⁇ 1 5% to 35% b ⁇ weight where the composition is in concentrated form.
  • the fabric softener composition ma ⁇ also optionall ⁇ 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 Pol ⁇ mers, emulsifiers, bacteriocides, colorants, perfumes, preservatives, optical brighteners, anti ionisation agents, antifoam agents and enz ⁇ mes.
  • conventional softening ingredients such as nonionic extenders, surfactants concentration aids, electrolyte concentration aids, stabilisers, such as well known antioxidants and reductive agents, Soil Release Pol ⁇ mers, emulsifiers, bacteriocides, colorants, perfumes, preservatives, optical brighteners, anti ionisation agents, antifoam agents and enz ⁇ mes.
  • the present invention is a process for preparing a composition as described herein before, which comprises the steps of a) mixing the surfactant and optional components, if an ⁇ , at a temperature above the melting point of the surfactant , b) preparing a waterseat, c) dispersing the mixture prepared in step a) in the waterseat, d) adding the betaine ester to d 1 )-the mixture prepared under point a), or d2)- the waterseat under point b), or d3)-the surfactant dispersion under c), or d4) combination of an ⁇ of the above, e) optionall ⁇ , cooling the resulting dispersion.
  • the molten mixture of step a) will be dispersed in a waterseat of step b) above the Krafft temperature of the surfactant.
  • the waterseat ma ⁇ optionall ⁇ contain additives such as pol ⁇ eth ⁇ lene gl ⁇ col or biocide.
  • Acids ma ⁇ be added in step a) or directl ⁇ to the waterseat of step b).
  • Optional components such as d ⁇ es, perfumes if present will be added either before step e) once the resulting dispersion is made or after step e).
  • B ⁇ 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 MJ ROSEN, Surfactants and interfacial phenomena, 1988, p.215.
  • CMC critical micelle concentration
  • the amount of shear should be sufficient to properl ⁇ disperse the surfactant. Proper dispersion can be verified b ⁇ controlling the particle size of the resulting dispersion, b ⁇ e.g microscop ⁇ or light scattering techniques. The particle size should preferabl ⁇ 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 t ⁇ pe of s ⁇ nthesis can also be convenientl ⁇ applied to the s ⁇ nthesis of N,N-dioct ⁇ lgl ⁇ cine phenoxan ⁇ l ester; N,N-dioct ⁇ lgl ⁇ cine cis-3-hexen ⁇ l ester as well as for N,N-didodec ⁇ lgl ⁇ cine phenoxan ⁇ l ester, N,N-didodec ⁇ lgl ⁇ cine cis-3-hexenyl ester and N,N-didodec ⁇ lgl ⁇ cine geran ⁇ l ester with the exception that for the three last one N,N-dioct ⁇ lgl ⁇ cine meth ⁇ l ester is used in the s ⁇ nthesis instead of N,N-dioct ⁇ lgl ⁇ cine meth ⁇ l ester.
  • the reaction mixture was stirred at 60°C for two weeks after which the reaction seemed completed b ⁇ 1 H NMR.
  • the sodium carbonate was filtered off, the filtrate was concentrated under vacuum and dieth ⁇ l ether (200 ml) was added before storage of the solution at 4°C for 1 2 hours. Then, the solution was filtered and removal of ether under vacuum ⁇ ielded to the expected N,N- didodec ⁇ lgl ⁇ cine linalyl ester as a ⁇ ellow oil.
  • This t ⁇ pe of s ⁇ nthesis can also be convenientl ⁇ applied to the s ⁇ nthesis of N,N-dioct ⁇ lgl ⁇ cine esters and N,N-didodec ⁇ lgl ⁇ cine esters of unhindered alcohols.
  • the N,N-dioct ⁇ lgl ⁇ cine esters h ⁇ drochloride or h ⁇ drobromide and the N,N-didodec ⁇ lglycine esters h ⁇ drochloride or h ⁇ drobromide can be easil ⁇ obtained b ⁇ dissolving N,N-dioct ⁇ lgl ⁇ cine esters or N,N-didodec ⁇ lgl ⁇ cine esters in an organic solvent such as methanol, ethanol, isopropanol, petroleum ether, dieth ⁇ l 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 solvent such as methanol, ethanol, isopropanol, petroleum ether, dieth ⁇ l ether, toluene
  • Linal ⁇ l chloroacetate (55.04 g, 200 mmol, 2 eq), in acetonitrile (75 ml), was slowl ⁇ added to dodec ⁇ lamine (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 b ⁇ 1 H NMR.
  • the sodium carbonate was filtered off, the filtrate was concentrated under vacuum and dieth ⁇ l ether (200 ml) was added before storage of the solution at 4°C for 1 2 hours.
  • This t ⁇ pe of s ⁇ nthesis can also be convenientl ⁇ applied to the chloroacetate or bromoacetate of unhindered alcohols such as geraniol, phenoxanol, cis-3- hexenol.
  • the h ⁇ drochloride or h ⁇ drobromide salts can be obtained b ⁇ dissolving for example N-but ⁇ l-N-(2-geran ⁇ lox ⁇ -2- oxoeth ⁇ Dgl ⁇ cine geran ⁇ l ester in an organic solvant such as methanol, ethanol, isopropanol, petroleum ether, dieth ⁇ l 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, dieth ⁇ l ether, toluene
  • Linal ⁇ l chloroacetate (82.56 g, 300 mmol, 3 eq), in acetonitrile (100 ml), was slowl ⁇ 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 b ⁇ 1 H NMR.
  • the sodium carbonate was filtered off, the filtrate was concentrated under vacuum and dieth ⁇ l ether (200 ml) was added before storage of the solution at 4°C for 1 2 hours. Then, the solution was filtered and removal of ether under vacuum ⁇ ielded to the expected N,N-bis(2-linal ⁇ lox ⁇ -2-oxoeth ⁇ l)gl ⁇ cine linal ⁇ l ester as a brown oil.
  • This t ⁇ pe of s ⁇ nthesis can also be convenientl ⁇ applied to the s ⁇ nthesis of chloroacetate or bromoacetate of unhindered alcohols such as geraniol, phenoxanol, cis-3-hexenol.
  • the h ⁇ drochloride or h ⁇ drobromide salts can be obtained b ⁇ dissolving for example N,N-bis(2-linalylox ⁇ -2-oxoeth ⁇ l)gl ⁇ cine linal ⁇ l 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
  • CTAB C1 6 trimeth ⁇ l ammonium bromide

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Abstract

Cette invention se rapporte à une composition et à un procédé pour préparer une telle composition, par laquelle on forme des composés d'ester de bétaïne stabilisés d'alcools actifs dans un milieu acide. Cette invention se rapporte en particulier à une composition acide aqueuse contenant: (a) un ester de bétaïne d'un alcool actif qui, à une concentration comprise entre 0,01 % et 10 % en poids de cette composition, est présent essentiellement sous la forme de micelles et/ou est capable d'être incorporé dans des micelles; (b) ainsi qu'un tensioactif; cette composition comprenant une substance acide en quantité suffisante pour rendre le pH de ladite composition inférieur à 7.
PCT/US1997/004959 1996-04-01 1997-03-27 Composes d'ester de betaine d'alcools actifs WO1997036978A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
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
CA002250837A CA2250837C (fr) 1996-04-01 1997-03-27 Composes d'ester de betaine d'alcools actifs
BR9710416A BR9710416A (pt) 1996-04-01 1997-03-27 Compostos de ïÕïster de betaina de alcoÄis ativos
AU25908/97A AU2590897A (en) 1996-04-01 1997-03-27 Betaine ester compounds of active alcohols
US09/155,779 US5958870A (en) 1996-04-01 1997-03-27 Betaine ester compounds of active alcohols

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP96302291A EP0799885A1 (fr) 1996-04-01 1996-04-01 Composés bétaine ester des aclcools actifs
EP96302291.3 1996-04-01

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BR (1) BR9710416A (fr)
CA (1) CA2250837C (fr)
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JP2024540307A (ja) 2021-11-03 2024-10-31 フイルメニツヒ ソシエテ アノニム 活性アルデヒドおよびケトンの光誘導放出のための環状アセタールおよびケタール
JP2024546881A (ja) 2021-12-14 2024-12-26 フイルメニツヒ ソシエテ アノニム エノールエーテルプロ香料
WO2024218086A1 (fr) 2023-04-17 2024-10-24 Firmenich Sa Acétals et cétals cycliques photolabiles pour distribution induite par la lumière d'aldéhydes et de cétones actifs
WO2025093456A1 (fr) 2023-11-03 2025-05-08 Firmenich Sa Proparfums de thiazolidine-4-carboxylate

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AR008583A1 (es) 2000-02-09
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JP2000509107A (ja) 2000-07-18
CA2250837C (fr) 2002-02-19
ZA972775B (en) 1997-10-24
EP0799885A1 (fr) 1997-10-08
CN1220693A (zh) 1999-06-23
CA2250837A1 (fr) 1997-10-09
AU2590897A (en) 1997-10-22

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