Field of the invention

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.

Background of the invention

Cleaning and laundry products are well known in the art. However, consumer acceptance of cleaning and laundry products is determined not only by the performance achieved with these products but also the aesthetics associated therewith. The perfume components are therefore an important aspect of the successful formulation of such commercial products.

Accordingly, formulations of compounds which provide a slow release of the perfume over a longer period of time than by the use of the perfume itself have been provided. Disclosure of such compounds may be found in WO 95/04809, WO 95/08976 and pending application EP 95303762.9. Pending application EP 95303762.9 describes betaine ester compounds of perfume alcohols which provide release of the perfume components over a long period of time.

Although 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 5 released upon and after the washing or cleaning process. By 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 10 environment but which still produces a slow release of the active alcohol (e.g perfume) upon and after the washing or cleaning process.

The Applicant has now found that the provision of 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. Preferably, said betaine esters have at least one long alkyl chain.

0 Therefore, 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. For optimum

25 benefit of storage stability and slow release of the active alcohol upon and after the washing or cleaning process, a cationic surfactant is preferred.

Not to be bound by theory, it is believed that the use of 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.

For the purpose of the invention, 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 .

By "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.

Summary of the invention

The present invention relates to 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.

In a preferred embodiment of the invention, the betaine ester is a hydrophobic betaine ester of formula:

wherein each R-| , R2, R3 independently, is selected from hydrogen, alkyl group, aryl group,

and

R '

(C H ₂ ) n 1 f ^■ <C H ₂ )n 1

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, wherein R4 is an alkyl group having from 7 to 19 carbon atoms, wherein each R' -| , R'2, independently, is selected from hydrogen, alkyl group, aryl group, -CH2-COOH, -CH2-COOR, -CH2-CH2-COOH and -CH2-

CH2-COOR, wherein each n, n-| , independently, is an integer lying in the range from 1 to

20, and wherein n2 is an integer lying in the range of 0 to 20, wherein each n3, independently, is an integer lying in the range from 1 to 3, and wherein each R, independently, is an organic chain of an active alcohol.

In another aspect of the invention a process for preparing said acidic composition is provided, whereby said process further improves the betaine ester protection from the acidic environment. A typical process for preparing a composition containing a surfactant 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.

Detailed description of the invention

Betaine ester compounds of active alcohols

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. Preferably, the betaine ester compounds of an active alcohol have the general formula below:

A -

wherein each R-j , R2, R3 independently, is selected from hydrogen, alkyl group, aryl group,

and

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, wherein R4 is an alkyl group having from 7 to 1 9 carbon atoms, wherein each R' -| , R'2, independently, is selected from hydrogen, alkyl group, aryl group, -CH2-COOH, -CH2-COOR, -CH2-CH2-COOH and -CH2- CH2-COOR, wherein each n, n-j , independently, is an integer lying in the range from 1 to 20, and wherein n2 is an integer lying in the range of 0 to 20, wherein each n3, independently, is an integer lying in the range from 1 to 3, and wherein each R, independently, is an organic chain of an active alcohol.

Preferably, each n2, independently, is an integer lying in the range of 0 to 6.

Preferably, each n3, independently, is an integer of value 1 or 2, more preferably 1 .

Preferably 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-| , R2 or R3 is an alkyl group having at least 8 carbon atoms. Preferably R' -| , R'2 are, each, independently selected from H, alkyl chain having 1 to 3 carbon atoms, phenyl.

For the above mentioned compounds, 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.

Preferably, for the above mentioned compounds, 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.

More preferred R groups, for the purpose of the invention, 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.

Other preferred compounds are selected from 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.

Other preferred compounds are selected from 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.

Other preferred compounds are selected from 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.

o

Other preferred compounds are selected from N-(2-geranyloxy-2-oxoethyl)- N,N-dimethyl-2-geranyloxy-2-oxoethanaminium bromide or chloride; N-(2- citronellyloxy-2-oxoethyl)-N,N-dimethyl-2-citronellyloxy-2-o xoethanaminium bromide or chloride; N-(2-linalyloxy-2-oxoethyl)-N,N-dimethyl-2-linalyloxy-2- oxoethanaminium bromide or chloride; N-(2-dihydromyrcenyloxy-2- oxoethyl)-N,N-dimethyl-2-dihydromyrcenyloxy-2-oxoethanaminiu m bromide or chloride.

Other preferred compounds are selected from 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-linalyloxy-2-oxoethyl)glycine linalyl ester hydrobromide or hydrochloride; N-butyl-N-(2-dihydromyrcenyloxy-2- oxoethyDglycine dihydromyrcenyl ester hydrobromide or hydrochloride.

Other preferred compounds are selected from 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-linalyloxy-2-oxoethyl)glycine linalyl ester hydrobromide or hydrochloride; N-dodecyl-N-(2-dihydromyrcenyloxy-2- oxoethyUglycine dihydromyrcenyl ester hydrobromide or hydrochloride.

Other preferred compounds are selected from 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.

Mixtures of any of the above components in the betaine ester used herein in the compositions of the invention may be used.

Preferably, 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.

Surfactant

The other essential component of the invention is a surfactant. Such surfactant are selected from anionic, nonionic, cationic, amphoteric and zwiterrionic surfactants.

Anionic surfactant

Essentially 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.

Other 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 _β -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-| - C4 alkyl) and -N-(C-j -C2 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 Cβ-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(CH2CH2θ) _x CH2COO-M ⁺ wherein R is a CQ to C-| 8 a'kyl 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 1 3 or less, and the average x is from about 3 to 10 when the average R is greater than C-| 3, 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 C12 ^t0 C18 ^a,k Y' 9 ^rou P-

Alkyl polyethoxy polycarboxylate surfactants suitable for use herein include those having the formula RO-(CHR- _| -CHR2-O)-R3 wherein R is a Cβ to Ci s alkyl group, x is from 1 to 25, R-] and R2 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-| or R2 is a succinic acid radical or hydroxysuccinic acid radical, and R3 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 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.

The following general structures further illustrate some of the preferred secondary soap surfactants:

A. 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.

B. 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.)

C. Still another preferred class of secondary soaps comprises secondary carboxyl compounds of the formula

CH ₃ (CHR) _k -(CH2)m-(CHR) _n -CH(C00M)(CHR) _o -(CH2) _p -(CHR) _q -CH3, wherein each R is C1 - 4 alkyl, wherein k, n, o, q are integers in the range of 0-8, provided that the total number of carbon atoms (including the carboxylate) is in the range of 10 to 18.

In each of the above formulas A, B and C, 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.

Other suitable anionic surfactants are the 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. Preferred examples are the myristyl and oleyl methyl sarcosinates in the form of their sodium salts.

Nonionic surfactant

Essentially any 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-| alkyl (i.e., methyl); and R2 is a C5-C31 hydrocarbyl, preferably straight-chain C5-C19 alkyl or alkenyl, more preferably straight-chain C9-C1 7 alkyl or alkenyl, most preferably straight-chain C1 1 -C1 7 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 a reducing sugar in a reductive amination reaction; more preferably Z is a glycityl.

The polyethylene, polypropylene, and polybutylene oxide condensates of alkyl phenols are suitable for use herein. In eneral, 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. 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 Cβ-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. Preferably 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. Preferably 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.

The 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. Examples of 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. (Optionally 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

R2θ(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 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 - (C2H4θ) _x H, where x is in the range of from 1 to 3.

Cationic surfactant

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:

I ) ditallow dimethylammonium chloride (DTDMAC); 2) dihydrogenated tallow dimethylammonium chloride;

3) dihydrogenated tallow dimethylammonium methylsulfate;

4) distearyl dimethylammonium chloride;

5) dioleyl dimethylammonium chloride;

6) dipalmityl hydroxyethyl methylammonium chloride; 7) stearyl benzyl dimethylammonium chloride;

8) tallow trimethylammonium chloride;

9) hydrogenated tallow trimethylammonium chloride;

1 0) C-| 2"14 alkyl hydroxyethyl dimethylammonium chloride;

I I ) Ci 2-1 8 ^a ' ^k y' dihydroxyethyl methylammonium chloride; 12) di(stearoyloxyethyl) dimethylammonium chloride (DSOEDMAC);

1 3) di(tallowoyloxyethyl) dimethylammonium chloride;

14) ditallow imidazolinium methylsulfate;

1 5) 1 -(2-tallowylamidoethyl)-2-tallowyl imidazolinium methylsulfate. 16) ditallow imidazoline

1 7) ditallow imidazoline ester

Also included within the scope of 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 :

(I) (ID

wherein Q is selected from -O-C(O)-, -C(O)-O-, -O-C(O)-O-, -NR -C(O)-, -

C(O)-NR ⁴ -;

R is (CH ₂ ) _n -Q-T ² or T ³ ;

R ² is (CH ₂ )m-Q-T ⁴ or Tδ 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, preferablγ 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.

Specific examples of quaternary ammonium compounds suitable for use in the aqueous fabric softening compositions herein include :

1 ) N,N-di(tallowyl-oxy-ethyl)-N,N-dimethyl ammonium chloride;

2) N,N-di(tallowyl-oxy-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium chloride; 3) N,N-di(2-tallowyl-oxy-2-oxo-ethyl)-N,N-dimethyl ammonium chloride; ' 4) N,N-di(2-tallowyl-oxy-ethylcarbonyl-oxy-ethyl)-N,N-dimethyl ammonium chloride;

5) N-(2-tallowyl-oxy-2-ethyl)-N-(2-tallowyl-oxy-2-oxo-ethyl)-N, N-dimethyl 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-ammo nium chloride; and 8) 1 ,2-ditallowyl-oxy-3-trimethylammoniopropane chloride; and mixtures of any of the above materials.

Of these, 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. Indeed, for compounds of Formula (I) made from tallow fatty acids having a IV of from 5 to 25, preferably 1 5 to 20, it has been found that a cis/trans isomer weight ratio greater than 30/70, preferably greater than 50/50 and more preferably greater than 70/30 provides optimal concentrability. For compounds of Formula (I) made from tallow fatty acids having a IV of above 25, the ratio of cis to trans isomers has been found to be less critical unless very high concentrations are needed. Other examples of suitable quaternary ammoniums of Formula (I) and (II) are obtained by, e.g. :

- replacing "tallow" in the above compounds with, for example, coco, palm, lauryl, oleyl, ricinoleγl, stearyl, palmityl, or the like, said fatty acyl chains being either fully saturated, or preferably at least partly unsaturated;

- replacing "methyl" in the above compounds with ethyl, ethoxy, propyl, propoxy, isopropyl, butyl, isobutyl or t-butyl;

- replacing "chloride" in the above compounds with bromide, methylsulfate, formate, sulfate, nitrate, and the like.

In fact, 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.

By "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.

Other 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.

Preferred among these 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 material

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 cationic surfactants above mentionned themselves.

Conventional acidic materials may also be used. Suitable conventional acidic materials include the bronstead acids as well as the fatty acids. Examples of 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.

More preferably, where cationic surfactants are used, especially those mentioned as biodegradable fabric softening agents, 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.

Typically 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.

Additional ingredients

Additional perfume ingredients may be added to the acidic composition. When present, the composition will comprise up to 5% by weight, more preferably from 0.1 % to 1 .5% by weight of additional perfume.

Additional 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. Many of the 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.

A wide variety of chemicals are known for perfume use including 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. Furthermore, the perfume can be formulated to provide desirable fruity odours e.g. lime, lemon or orange.

Particular examples of optional 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, dihγdrolinalool, 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, methγl anthranilate, alpha-methyl ionone, methγl nonγl acetaldehγde, methγl phenγl carbinγl acetate, laevo- menthγl acetate, menthone, iso-menthone, mγrcene, mγrcenγl acetate, mγrcenol, nerol, nerγl acetate, nonγl acetate, phenγl ethγl alcohol, alpha- pinene, beta-pinene, gamma-terpinene, alpha-terpineol, beta-terpineol, terpinγl acetate, vertenex (para-tertiarγ-butγl cγclohexγl acetate), amγl cinnamic aldehγde, iso-amγl salicylate, beta-carγophγllene, cedrene, cinnamic alcohol, couramin, dimethγl benzγl carbinγl acetate, ethγl vanillin, eugenol, iso-eugenol, flor acetate, heliotrophine, 3-cis-hexenγl salicylate, hexyl salicylate, lilial (para-tertiarybutyl-alpha-methyl hγdrocinnamic aldehγde), gamma-methγl ionone, nerolidol, patchouli alcohol, phenγl hexanol, beta-selinene, trichloromethγl phenγl carbinγl acetate, triethγl citrate, vanillin, veratraldehγde, alpha-cedrene, beta-cedrene, C1 5H24sesquiterpenes, benzophenone, benzγl salicylate, ethylene brassylate, galaxolide (1 ,3,4,6,7, 8-hexahγdro-4,6,6,7,8,8,-hexamethγl- cγclo-penta-gamma-2-benzopγran), hexγl cinnamic aldehγde, Iγral (4-(4- hγdroxγ-4-methγl pentγl)-3-cγclohexene-1 0-carboxaldehγde), methγl cedrγlone, methγl dihγdro jasmonate, methγl-beta-naphthγl ketone, musk ambrette, musk idanone, musk ketone, musk tibetine, musk xγlol, aurantiol and phenγlethγl phenγl acetate and mixtures thereof.

The compositions according to the present invention are suitable for use where acidic products and surfactants, preferablγ a cationic surfactant are present. Such acidic products include fabric softeners, hard surface cleaners, bathroom cleaners, shower gels, deodorants, bars, shampoos, conditioners.

Fabric softener compositions

When used as a fabric softener composition, the cationic surfactants which also act as fabric softener will preferablγ be present, depending on the composition execution, in amount of 1 % to 8% bγ weight where the composition is in diluted form or in amount of 8% to 80%, more preferablγ 1 0% to 50%, most preferablγ 1 5% to 35% bγ weight where the composition is in concentrated form.

The fabric softener composition maγ also optionallγ 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 Polγmers, emulsifiers, bacteriocides, colorants, perfumes, preservatives, optical brighteners, anti ionisation agents, antifoam agents and enzγmes.

Process

Also provided herein bγ 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 anγ, 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 anγ of the above, e) optionallγ, cooling the resulting dispersion.

Preferablγ the molten mixture of step a) will be dispersed in a waterseat of step b) above the Krafft temperature of the surfactant.

The waterseat maγ optionallγ contain additives such as polγethγlene glγcol or biocide.

Acids maγ be added in step a) or directlγ to the waterseat of step b). Optional components such as dγes, perfumes if present will be added either before step e) once the resulting dispersion is made or after step e).

Preferablγ, during dispersion of the betaine ester in step d3), care should be taken that the temperature of the molten mixture is above the Krafft temperature of the surfactant. Bγ 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.

It is also preferred to apply sufficient shear to ensure adequate incorporation of the betaine ester into the micelles/vesicles. The amount of shear should be sufficient to properlγ disperse the surfactant. Proper dispersion can be verified bγ controlling the particle size of the resulting dispersion, bγ e.g microscopγ or light scattering techniques. The particle size should preferablγ be below 50μm.

With regard to 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.

Not to be bound bγ theory, it is believed that such a process provides effective protection of the weak ester linkage of the betaine ester by shielding it from water; thus avoiding premature hydrolysis during storage. Preferably, for optimum protection provided bγ this process, the surfactant used is a cationic surfactant.

Perfume synthesis examples

1 -Synthesis of N,N-dioctylglycine esters and N,N-didodecylglvcine esters of unhindered alcohols by transesterification

To a mixture of N,N-dioctylglγcine methγl ester (47.02 g, 1 50 mmol, 1 eq) in toluene (250 ml) under argon was slowlγ added some sodium methoxide (1 .01 g, 0.01 9 mol, 0.1 25 eq) and geraniol (27.3 ml, 1 58 mmol, 1 .05 eq). The mixture was heated under vacuum (10 mm Hg) and the methanol produced bγ the transesterification reaction is distilled with toluene over one hour after which the reaction appeared completed by 1 H NMR. Any remaining toluene is evaporated under vacuum. Diethyl ether was added (200 ml) and the mixture stored at 4°C for one hour prior to filtration. The filtrate was then concentrated under vacuum yielding to the expected N,N- dioctγlglγcine geranγl ester as a light γellow oil (quantitative γield).

This tγpe of sγnthesis can also be convenientlγ applied to the sγnthesis of N,N-dioctγlglγcine phenoxanγl ester; N,N-dioctγlglγcine cis-3-hexenγl ester as well as for N,N-didodecγlglγcine phenoxanγl ester, N,N-didodecγlglγcine cis-3-hexenyl ester and N,N-didodecγlglγcine geranγl ester with the exception that for the three last one N,N-dioctγlglγcine methγl ester is used in the sγnthesis instead of N,N-dioctγlglγcine methγl ester.

2-Svnthesis of N.N-dioctylqlγcine esters and N,N-didodecylglvcine esters of hindered alcohols (tertiary alcohols) using their chloroacetate or bromoacetate

Dihγdromγrcenγl bromoacetate (27.7 g, 100 mmol, 1 eq), in ethγl acetate (50 ml), was slowlγ added to dioctγlamine (33 ml, 1 10 mmol, 1 .1 eq) and sodium carbonate (21 .2g, 0.2 mol, 2 eq), in ethγl acetate (100 ml). The reaction mixture was stirred at ambient temperature for 72 hours after which the reaction seemed completed bγ 1 H NMR. The sodium carbonate was filtered off, the filtrate was concentrated under vacuum and diethγl 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 γielded to the expected N,N-dioctγlglγcine dihγdromγrcenγl ester as a γellow oil (38.05g, 87% γield).

Linalγl chloroacetate (5.77 g, 25 mmol, 1 eq), in toluene (50 ml), was slowlγ added to didodecγlamine (10 g, 28.3 mmol, 1 .1 3 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 bγ 1 H NMR. The sodium carbonate was filtered off, the filtrate was concentrated under vacuum and diethγl 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 γielded to the expected N,N- didodecγlglγcine linalyl ester as a γellow oil.

This tγpe of sγnthesis can also be convenientlγ applied to the sγnthesis of N,N-dioctγlglγcine esters and N,N-didodecγlglγcine esters of unhindered alcohols.

In all these experiments, the N,N-dioctγlglγcine esters hγdrochloride or hγdrobromide and the N,N-didodecγlglycine esters hγdrochloride or hγdrobromide can be easilγ obtained bγ dissolving N,N-dioctγlglγcine esters or N,N-didodecγlglγcine esters in an organic solvent such as methanol, ethanol, isopropanol, petroleum ether, diethγl ether, toluene and adding at least a stoechiometric amount of mineral acid in water or in an organic solvant (such as HCl in isopropanol).

3-Svnthesis of N-dodecyl-N-(2-qeranyloxy-2-oxoethyl)qlγcine geranyl ester bv transesterification (alcohol unhindered)

To a mixture of N-dodecγl-N-(2-methoxγ-2-oxoethγl)glγcine methγl ester (6.59 g, 20 mmol, 1 eq) in toluene (80 ml) under argon was slowlγ added some sodium methoxide (0.27 g, 0.005 mol, 2 *0.125 eq) and geraniol (7.3 ml, 42 mmol, 2* 1 .05 eq). The mixture was heated under vacuum (10 mm Hg) and the methanol produced bγ the transesterification reaction was distilled with toluene over two hours after which the reaction appeared completed bγ 1 H NMR. Anγ remaining toluene was evaporated under vacuum. Diethγl ether was added (200 ml) and the mixture stored at 4°C

for one hour prior to filtration. The filtrate was then concentrated under vacuum γielding to the expected N-dodecγl-N-(2-geranγloxγ-2- oxoethγDglγcine geranγl ester as a light brown oil (quantitative γield).

This type of synthesis can also be convenientlγ applied to the synthesis of N-dodecyl-N-(2-phenoxanγloxγ-2-oxoethγl)glγcine phenoxanγl ester and N- dodecyl-N-(2-cis-3-hexenyloxγ-2-oxoethγl)glγcine cis-3-hexenγl ester as well as for the sγnthesis of N-butγl-N-(2-geranγloxγ-2-oxoethγl)glγcine geranγl ester, N-butγl-N-(2-phenoxanγloxγ-2-oxoethγl)glγcine phenoxanγl ester and N-butγl-N-(2-cis-3-hexenγloxγ-2-oxoethγl)glγcine cis-3-hexenγl ester with the exception that for the three last one N-butγl-N-(2-methoxγ-2- oxoethγDglγcine methγl ester is used in the sγnthesis instead of N-dodecγl- N-(2-methoxγ-2-oxoethγl)glγcine methγl ester.

4-Svnthesis of N-dodecyl-N-(2-linalyloxy-2-oxoethyl)glvcine linalyl ester or N-dodecyl-N-(2-dihvdromyrcenyloxy-2-oxoethγl)glγcine dihydromyrcenyl ester (stericallv hindered alcohol such as tertairv alcohols) using their chloroacetate or bromoacetate

Dihγdromγrcenγl bromoacetate (55.44 g, 200 mmol, 2 eq), in acetonitrile (75 ml), was slowlγ added to dodecγlamine (24.2 ml, 100 mmol, 1 eq) and sodium carbonate (42.4 g, 0.4 mol, 4 eq), in acetonitrile (250 ml). The reaction mixture was stirred at ambient temperature for 48 hours after which the reaction seemed completed bγ 1 H NMR. The sodium carbonate was filtered off, the filtrate was concentrated under vacuum and diethγl 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 γielded to the expected N-dodecγl-N-(2-dihγdromγrcenγloxγ-2- oxoethγDglγcine dihγdromγrcenγl ester as a brown oil (56.2 g, 97.2% γield).

Linalγl chloroacetate (55.04 g, 200 mmol, 2 eq), in acetonitrile (75 ml), was slowlγ added to dodecγlamine (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 bγ 1 H NMR. The sodium carbonate was filtered off, the filtrate was concentrated under vacuum and diethγl 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 γielded to the expected N- dodecyl-N-(2-linalyloxγ-2-oxoethγl)glγcine linalyl ester as a brown oil (48.6 g, 84.7% yield).

Synthesis of N-butyl-N-(2-linalγloxγ-2-oxoethγl)glγcine linalyl ester and N- butγl-N-(2-dihγdromγrcenγloxγ-2-oxoethγl)glγcine dihγdromγrcenγl ester is made as above with the exception that butγlamine is used in the sγnthesis instead of dodecγlamine

This tγpe of sγnthesis can also be convenientlγ applied to the chloroacetate or bromoacetate of unhindered alcohols such as geraniol, phenoxanol, cis-3- hexenol.

In all these experiments, the hγdrochloride or hγdrobromide salts can be obtained bγ dissolving for example N-butγl-N-(2-geranγloxγ-2- oxoethγDglγcine geranγl ester in an organic solvant such as methanol, ethanol, isopropanol, petroleum ether, diethγl 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).

5-Svnthesis of N.N-bis(2-geranγloxy-2-oxoethyl)glγcine oeranyl ester bv transesterification (or anv unhindered alcohol)

To a mixture of N,N-bis(2-methoxy-2-oxoethγl)glγcine methγl ester (7.0 g, 30 mmol, 1 eq) in toluene (80 ml) under argon was slowlγ added some sodium methoxide (0.49 g, 0.009 mol, 3*0.10 eq) and geraniol (14.57 g, 95 mmol, 3* 1 .05 eq). The mixture was heated under vacuum (10 mm Hg) and the methanol produced bγ the transesterification reaction is distilled with toluene over two hours after which the reaction appeared completed bγ 1 H NMR. Anγ remaining toluene is evaporated under vacuum. Diethγl ether was added (200 ml) and the mixture stored at 4°C for one hour prior to filtration. The filtrate was then concentrated under vacuum γielding to the expected N,N-bis(2-geranγloxγ-2-oxoethγl)glγcine geranγl ester as a γellow oil (quantitative γield).

This type of synthesis can also be convenientlγ applied to the sγnthesis of N,N-bis(2-phenoxanγloxγ-2-oxoethγl)glγcine phenoxanγl ester and N,N- bis(2-cis-3-hexenyloxγ-2-oxoethγl)glycine cis-3-hexenyl ester.

6-Svnthesis of N.N-bis(2-linalyloxy-2-oxoethyl)qlvcine linalyl ester or N.N- bis(2-dihvdromyrcenyloxy-2-oxoethyl)glvcine dihydromyrcenyl ester

(stericallv hindered alcohols such as tertairv alcohols) using their chloroacetate or bromoacetate

Dihydromγrcenγl bromoacetate (83.1 6 g, 300 mmol, 3 eq), in acetonitrile (100 ml), was slowlγ 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 sealed and stirred at ambient temperature for 48 hours after which the reaction seemed completed bγ 1 H NMR. The sodium carbonate was filtered off, the filtrate was concentrated under vacuum and diethγl 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 γielded to the expected N,N- bis(2-dihγdromγrcenγloxγ-2-oxoethγl)glγcine dihγdromγrcenγl ester as a brown oil.

Linalγl chloroacetate (82.56 g, 300 mmol, 3 eq), in acetonitrile (100 ml), was slowlγ 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 bγ 1 H NMR. The sodium carbonate was filtered off, the filtrate was concentrated under vacuum and diethγl 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 γielded to the expected N,N-bis(2-linalγloxγ-2-oxoethγl)glγcine linalγl ester as a brown oil.

This tγpe of sγnthesis can also be convenientlγ applied to the sγnthesis of chloroacetate or bromoacetate of unhindered alcohols such as geraniol, phenoxanol, cis-3-hexenol.

In all these experiments, the hγdrochloride or hγdrobromide salts can be obtained bγ dissolving for example N,N-bis(2-linalyloxγ-2-oxoethγl)glγcine linalγl 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).

The invention is illustrated in the following non-limiting examples, in which all percentages are on a weight basis unless otherwise stated.'

In the examples, the abbreviated component identifications have the following meaning:

DEQA Di-(tallowoγl-oxγ-ethγl) dimethγl ammonium chloride

Fatty acid Stearic acid of IV = 1

Electrolyte Calcium chloride

DGGE N-dodecγlglγcine geranγl ester hγdrochloride

PEG Polγethγlene Glγcol 4000

CTAB C1 6 trimethγl ammonium bromide

Cetrimide C14 trimethγl ammonium bromide

Dobanol® 23-3 C1 2-C1 3 ethoxγlated alcohol with an average degree of ethoxγlation of 3, available from Shell

Lutensol® AO 30 C1 3-1 5 alcohol ethoxγlated with an average degree of ethoxγlation of 30, available from BASF

Dobanol® 91 -10 C1 9-C21 ethoxγlated alcohol with an average degree of ethoxγlation of 10, available from Shell

Dobanol® 23-6.5 C1 2-C1 3 ethoxγlated alcohol with an average degree of ethoxγlation of 6.5, available from Shell

Alkγl sulphate Based on Isalchem 1 23 ® alcohol, C12-1 3 alcohol, 94% branched, available from Enichem

Example 1

The following fabric softening compositions according to the present invention were prepared:

Component A B C D E

DEQA 2.6 2.9 1 8.0 1 9.0 1 9.0

Fatty acid 0.3 - 1 .0 - -

Hydrochloride acid 0.02 0.02 0.02 0.02 0.02

PEG - - 0.6 0.6 0.6

Perfume 1 .0 1 .0 1 .0 1 .0 1 .0

Silicone antifoam 0.01 0.01 0.01 0.01 0.01

DGGE 1 0.5 1 0.5 1

Electrolyte - - 600ppm 600ppm 1 200ppm

Dγe 10ppm 10ppm 50ppm 50ppm 50ppm

Water and minors to balance to 100

Example 2

The following hard surface cleaner compositions according to the present invention were prepared bγ mixing the listed ingredients

water and miscellaneous to balance pH as is 1 .0 0.9 4.0 3.2