CA2119767A1

CA2119767A1 - Concentrated fabric-softening compositions

Info

Publication number: CA2119767A1
Application number: CA002119767A
Authority: CA
Inventors: Hugo Jean Marie Demeyere; Johan Maurice Theo De Poortere
Original assignee: Individual
Current assignee: Procter and Gamble Co
Priority date: 1991-09-27
Filing date: 1992-09-21
Publication date: 1993-04-01
Also published as: JPH07505189A; MX9205493A; WO1993006294A1; EP0534009B1; PT100908A; AR246566A1; EP0534009A1; IE922689A1; ES2080241T3

Abstract

Concentrated fabric-softening compositions are disclosed, containing at least 10 % by weight of a di-long chain imidazoline ester, preferably ditallowimidazoline ester, and having a pH below 4, characterized in that they contain from 0.01 % to 1 % of a chelating agent for heavy metal ions, to cure perfume off-note development under storage.

Description

WO 93/06294 Pcr~uss2/o8o48 ::ONC:ENr~ATED FABRIC SOFTENING COMPOSITIONS

~ ~_ r i e, I ~ ' ,, ,_ The pre~;~n~ invention relates tc) e:o~centrated ~Eabric-~oftening co~po~; tions in liqu~ d form, to be :~
used in ~he rinse step of the laundry cycle.

~8Qk~8!~

Fabric-sof~ening compc~sitions to be added in the rinse step of a laundry cycle are well known in the art and have f ound wide-scal~ commercial application .

In addition tc~ achieving excellent fa}:ri~-softening p~rf orm~nce, it has been, in recent y~ars, the obj ec~i~e of fabrio softener manu~acturers t~ pr~Yide compositions which haYe an increased biodegradabi lity .

P.ccordingly, ester-corltairling fabric~softeniIIg actives have been disclosed, to be used in replacemenl:
of, or in combination with , conventional ~uaternary s~f~ening actives. Such ester-containing actives include the imidazol ine ester derivatives disclosed in SaJBSTlTllrE SHlE~Fr WO ~3/06294 PCI /U~i92/08048 211!~767 P . g. GB 1, 561, ~08 and further disclosed in e . g . EP-A-345 842.

It has been f ound, ~owever ~ that concentrated c:ompositions con~aining said ester imidazoline compounds have a tendency to develop an odor off-note, on prolonged storage.

The present invention is based on the discovery that such a problem is surprisingly cured by the incorporation in said concentrated compositions of a small amount of chelating agent for heavy metal ions .

In U . S . Patent 3, 756 ~ 950 are disclosed fabric-softening compositions cor~taining conventional ~:~
qtaaternary ammonium so*tening actives and an acid s~lt of amino-carboxylic acid chelating gent, to decrease fabric yellowing.

Summary of th~e Inventic: n The present invention encompasses c:oncentrated fabric-softening compositions containing at least 10%
by weight, preferably 15 to 25% by weight of an imidazoline ester softening actiYe of the formula:

( C~2 ) T~
/ \
N ~ N ~ H2)n - O - C - Xl X

wherein X and X1 are, independently, C11-C2~
hydrocaxbyl groups, preferably C13 C17 alkyl, and m and n are , independently , from 2 to 4, preferably 2, and a Bronsted~ acid as levels such as to have a pH
below 4, characterized in that, it contains a chelating agent for heavy metal ions, at levels of from 0 . 019~ to 1%, preferably 0. 05 to 0 . 2% . o~ the cc:mposition .

WO 93/062g4 PCT/US92/0~048 Detailed Description_of the Invention Substitu$ed_imidazoline ester softeninq comPou~

The compositions of the present invention contain at least 10~, preferably from 15% to 25% of a substituted imidazolln2 ester softening compound having the formula (C~I2)m / \ ~
(b) N ~ N ~ (C~2 ) n - o - ~ _ Xl wherein X and Xl are, independently, Cll-C21 hydrocarbyl groups, preferably C13-C17 alkyl, most pre~erably straight chain C17 alkyl, and m and n are, independently, from 2 to 4, pre.ferably m and n are hoth 2. The total concentration of softener active cannot exceed about ~0~ by weight. It will be understood that substituents X and X1 m7y optionally be substituted with various yroups such as alkoxyl, hydroxyl, or can be branched, but suc~ materials are no~ preferred herein. In ad~ition X and/or X1 may optionally be unsaturated (i.e., alkenyl groups~. The preferred substituted imidazoline ester softening compounds will hereina~ter be referred to as di-alkyl imidazoline ester compounds. Most pre~erred is ditallow imidaxoline ester.

' The pH, measured in distilled water at 3% dilution o~ the prese~t compositions should be not ~reater than 4, preferably from 2~5-40 WO 93/06~94 PCr/US92/0804 119 7 6 7 To achieve such a pH, a Bronstedt acid having a pKa value of 6 or less, is present in the present composltion.

Examples of suitable acids include the inorganic mineral acids, carbc: xylic aGids, in particular the low molecular weight tC1-C5) carboxylic acids, aromatic carhoxylic acids, like benzoic acid, and alkylsulfoni acids .

Suitable ionorganic acids include HCl, HBr, H2SO4, HNO3 and H3PO4. Suitable organic: acids include benzoic a~::id, formic, acetic, methylsulfoni~: and ethylsul~onic ac:id. Preferred acids are phosphoric, formic, an~ methylsul onic acid.

Liauid carrier The composi$ions herein comE~rise a 1 iquid carri~r, e~,g., water, preferably a mixture of wat~r and a Cl C4 monohydric alc:ohol ( e . g ., ethanol , propanol , isopropanol, butanol, and mixtures thereof ), isopropanol bein~ preferred. These compositic:~ns comprise ~rom 60% to 98~, praferably from 70% to 95~6 of the liquid carrier~ Preferably, the amount of the Cl-C4 morlohydric alcohol in the liquid carrier is from 5% to 50% by weight of the softening compounds, the balance of ~he 1 iquid carrier being water .

The ch~ ~heavy metal ions .

The ::helating agents are present at levels of from 0. 01% to 1% of the compositions herein, preferably from 0.05 to 0.2%.

The chelating agents for hea~ry metal ions useful ~erein include any material known in the art f or that purpose .

W093~06294 PCT~US92/0804X

Suitable compounds include the following carboxyllc acids and salts thereof : citric acid, tartaric acid, oxydisuccinic acid, ethylene diamine -N,N disuccinic acid, oxydiacetic acid, carboxymethyltartronic acid, carboxymethyloxysuccinic acid, tartrate monosuccinic acid/tartrate disuccinic acid blend at 80:20 weight ratio, as well as 2-dodecenyl succinic acid, and dodecyl succinic acid.

This category also includes polycarboxylic acids and salts thereof, such as polyacrylates and c:op~lymsrs of maleic and ac:rylic acids.

Other suitable compounds are the fc; llowing amino~
car~oxylic acids and salts thereof, as nitrilotriacetic acid, ethylene diamine tetracetic acid, cyclo e~hylene diamine tetracetic acid, trans 1,2 diamino cyclohexane N,N,N',N' tetraacetic mo~ohydrate ~CHELCD), hydroxyethylenediamine tetracetic acid, diethylene tri,aminopentacetic acid, N-glyceryl imino diacetic acid, N(-2 hydroxypropyl) .iminodi2ce~ic acid;

Polyamino polyalkylene phosphonic acids and salts thereof such as ethylenediamine tetramethylenephosphonic acid and diethylene triamine pentamethylenephosphonic acid are also suitable as chelating agents her~of.

Optional inqredlents Fully-formulated fabric softening compositions may optionally contain, in addition to the substituted imidazoline ester softening compounds of the formula herein, the liquid carrier and the acid, one or more of the ~ollowing ingredients.

W~ 9~0~294 P~rtus92/0804

2 11~ 7 6 7 Ouaternar~ ammonium softeninc~ aqents The compositions of the present invention can further comprise a di (hiyher alkyl) quaternary ammonium softening agent. The compcsitions herein can contain from 0% to 25% ~preferably from 0.1% to 10%) of the di thigher alkyl) quaternary ammonium softening agent .

The quaternary softelling agents useful herein are selected from the group of ( i ) acyt~ quaternary ammonium salts having the formula:
1 2 +

R2--N ~ R3 A

R~, _ wherein R2 is an acyclic aliphatic C15-C:22 hydrot-arbon group which may he interupted by ester groups. R3 is a Cl-C4 saturated alkyl or hydroxyalkyl gxoup, R4 is selected from R2 and R3, and A is an anion;

P~apidly biodegradable compounds of formula ( i) where R2, and possibly R4, are interupted by ester groups, are disclosed in EPA 239 910.

( ii) diamido c~aternary ar~monium salts having the formula:

R5 ~ :
11 1 i1 '' ~1 C--NH--R2 -- N --R2 ---NH--C --Rl A-_ _ WO~3/0629q PCT/~S92/0~048 wherein Rl is an acyclic aliphati~ C15 C22 21 1 9 7 6 7 hydrocarbon group, R2 is a divalent alkylen~ group having 1 to 3 carbon atoms, R5 and R8 are Cl-C4 saturated alkyl or hydroxyalkyl groups~ and A- is an anion;

(iii) diamido alkoxylated quaternary ammonium salts having the formula :
R5 O +

R~ C - NH ~2 N -R2 - NH ~ C - R1 A-~CH2cH20)nH

wherein n is equal to from 1 to 5 r and Rl, R2, R~
and A- are as defined above.

(iv) quaternary lmidazolinium co~pounds having the formul~ :

~ / R2 N N

Rl \ c~2~2ZCRl ~_ wherein Rl = C15-C17 saturated alkyl, R2 = Cl-C4 sa~urated alkyl, Z = NH or O, and A- is an anion.

Examples of Component (i) are the well kn~wn dialkyldimethylammonium~ salts such as ditallowdimethylammonium chloride, ~-dital lowdi~ethylammonium methylsulfate, di ~hydrogenated tallow) dimethylammonium chloride, dibehenyldimethyla~Mnonium chloride.

ExamI?les OL Component ( ii ) and ( iii ) ar~
methylbis(tallowamidoethyl) (2-hydroxyethyl) ammonium methylsulfate and methylbis(hydrogenated tall~wamid~ethyl) (2-hydroxyethyl) ammonium methylsulfate, wherein Rl is an acyclic aliphatic Cls-.'~ WOg3/062g4 PCT~US92/0804~
} , . l, , ~1 197 6 l C17 hydrocarbon group, R2 i~ an ethylene group, R5 is a methyl group, R8 is a hydroxyalkyl group and A is a methylsulfate anion; these materials are available i~ from Sherex Chemical Company under the trade names ~ VarisoftR 222 and VarisoftR llo, respectively.
''~''' Examples of component ~iv) are l-methyll-tallowamino-ethyl ~-tallowimidazolinium methylsulfate and l-methyl-1-(hydrogenated tallowamidoethyl~-methylsulfate.

The ratio of ~uaternary ammonium salt to cyclic-amine should not exceed 10:1, and preferably does not exceed 2:1.
~.' ~-~ The aqU0US dlspersion of ~uaternary softening agent 2, iS prepared in a conventional way, typically by inject~ng the quat~rnary material in a molten form in a batch containing water, with continuous agitation.
~`,2~

Once this dispersi~n is prepared, the concentrated composi~ion resulting from steps a) to d) will be added to it.

In case af a continuous process, said concentrated composition will, immediately after step d) be added to ~he aqueous dispersion of quaternary ammonium .. compound.
'~ . ,11 :~, In an alternative and convenient way, the concentrated composition obtained a~ter step d) will first be ooled to a temperature of from 15 to 25-C, ~ (room temperature) and then some time will be allowed ,~ for e.g. storage, shipment of the concentrated compos~tion, before it is added to the aqueous dispersion of quaternary softening agent.

.~ In any case, the ~iscosity of the finished product s~.~ will be in a range of 20 to 500 cp, preferably 50 to ~. 150 ~p.

,.~,.
.~

W093~06294 PCT/US9~/~8048 9 ~119767 OPtional cQ-softeninq aqents The co-softening agents for use herein can be selected from fatty acid esters of polyhydric alcohols having up to 8 carbon atoms such as described in DE-A-26 31 114. Examples of the likP est~rs includP
sorbitan esters and glycerol esters such as sorbitan monostearate, sorbitan monool~ate, glycerol mono-di-I and tri-fatty acid ester~ wherein th~ acid i5 SeleGted from stearic, oleic~ lauric, ~apric9 caprylic, caproic, valeric, butyric, propionic and acetic acid;
an individual glycerol can be esterified by identical fatty acid groups or by mixed es~ers e.g. glycerol monostearatedioleate. Polyethyleneglycol esters ~-~ monostearate, wherein the polyethyleneglycol moie~y has a molecular weight in the range from 200 to 400 are also included in that cla~s. Fatty acid esters of monohydric alcohols having at least 4 carbon atoms such as isobutyl stearate and ethyl hexyl stearate can also be useful.

Additional co softening agents which can be used are : glycerol, diglycerol, ekhylene glycol, propylQ~e glycol, diethylene glycol, dipropylene glycol, dihexylene glycol, polyethylene glycol (MW 200-loo.ooo), polypropylene glycol (~W 200-lOo.ooo), polyvinylalcohol, polyoxyethylenepolyoxypropylene copolymers, polypropylene glycol tMW 900), glucos~
methylether, butyldiglycolether, diethyleneglycolmonol~utylether, propyleneglycolmonoethyl or ethyl ether, ethylene carbonate, propylene carbonate.

Useful also are alkylpolyglucosides of the general fo~mula R20(CnH2nO~t ~glucosyl~x wherein R2 is alkyl, alkylphenyl, hydroxyalkyl, hydroxyalkylphenyl and mixtures thereo~ wherein the alkyl chain has ~rom 8 to 18 c rbon atoms, t is from 0 to 2 and x from 2 to 7, can also be used in the composition. These gluco5ides W093/06294 PCT/US92/0~8 119~ 6~exhibit desirable solvent properties and in addition can confer fiber benefits such as softness.

Lanolins and derivatives and paraffins having from 16 to 20 carbon atoms cvn5titute another example of non-ionic agents which can be used if desired~ Low melting oils from animal, vegetable or mineral origin are representati~e of this class of materials.
Carna~ion oil~, Jojoba oilR and Sunflower oil are speci~ic examples which are found to work~

Another important class of co softening agents is represented by materials of the general formula :

RlCOOR~

wherPin Rl is a strai~ht or branched chain a~ kyl or alkenyl group having from 8 to 23 carbon atoms and R2 is hydrogen or an alkyl or hyclroxyalkyl group having 1-4 carbon atoms.

Xighly preferred materials of this c~ass are the C1O
to C20 saturated fatty acids, especially lauric acid, myristic acid, palmitic acid and stearic acid.

Also suitable arP linear fatty Cg_1~ akanol ethoxylates such as LUTENSO ~ compounds aYailable from BASF, as well as ~ranched C8_18 akanols such as EXXAL
compounds available from EXXON.

Clay materials such as the low ion-exchange-capacity ones describerd in EPA 150.531 can also be used.

The co-softening a~ents above can be used in combination with cation-actiYe amines, namely primary, secondary and tertiary amines ha~ing, at least, one straight-chain organic group of from 12 to 22 carbon atoms. Preferred amines of this class are ethoxyamines, such as monotallow-dipolyethoxyamine, having a total of 2to 30 ethoxygroups per molecule, W093/06294 PCT/US92/0~04~

Suitable are also diamines such~as tallQw-N,N~, N~- 21 1 9 7 6 7 ~ris (2-hydroxyethyl)-1,3 propylenediamine, or C16~18-alkyl-N-bis(2-hydroxyethyl) amines, examples of above ami~es are ~hese sold under the trade name GENAMIN C, S, D, and T, by Hoechst.

The co~softening agents above are used at ratios of from 5:1 of 20:1 o~ quaternary softening agent to co-softening agent.

In the instance for fatty acids are used, a preferred ra~io is from 8:1 to 10:1.

Further other optional ingredients for use herein include silicone components such as described in British Patent No. 1,549,180, emu~sifiers, preservatives, g~rmicides, dyes, bac~ericides, stabil zers, briqhteners, opa~ifiers, photoactivators, copolymeric carboxyla~es having seguestQring properties, soil release agents, bleaches, bleach acti~ators, ~nd anti-yellowing agents. S~itable polyme~ic soil-release agent~ are disclosed in EP-A-220 156.

These additi~es ar~ normally incorporated at their conventional low le~els ~-.g. from 0.001% to 5%, in the dilution step of the concentrates herein.

W0~3/06294 P~T/US92/08048 The following examples illustrate the present inventionO
The followina~comPositions were ~repared :

T2~1R 1 ___ _ __ E~ 13X 2 Ditallow Imidazoline Ester 20 22 Perfume 0.80 0.80 Polydimethyl siloxane 0.2 0.2 Soil Release Poly~er 0.2 Q.2 Citric acid OA 1 0~ 05 CaC12 0.2 0.2 water and minors Balance p~I 3 % 3 .. O

~-~ The compo~itions of Example 1 and 2 were stored for

3 weeks at 50'C and compared with similar compositions not containing citric acid~ stored under the same conditions: the compositions of Exampl~ 1 and 2 did not develop any perfum~ off-nol:e, contrary t~ the reference compositions.

The foll win~_ç. _ ~a~ 2 Dittalow Imidazoline Ester 21 22 23 23 Perfume 0.7 0.7 0.8 0.7 Polydimethyl siloxane 0.2 - 0.2 Soil Release Polymer O.2 0.2 -Dequest 2066* 0.1 EDTA disodiumsalt - 0.1 CHELCD** - - 0.05 Tartaric Acid - - - 0.1 water and minors ------~ Balance ----~

* diethylene triamine pentamethylena phosphonic acid ** trans 1,2 diamino cyclohexane N,N,N',N' tetra~
acetic monohydrate

Claims

What is claimed is:

1. A concentrated fabric-softening composition containing at least 10% by weight of an imidazoline ester softening active of the formula:

wherein X and X1 are, independently, C11-C21 hydrocarbyl groups, preferably C13-C17 alkyl, and m and n are, independently, from 2 to 4, preferably 2, and a Bronstedt acid as levels such as to have a pH below 4, characterized in that, it contains a chelating agent for heavy metal ions, at levels of from 0.1% to 1% ofthe composition.

2. The composition of claim 1 wherein said imidazoline ester is ditallow imidazoline ester.

3. The composition of claim 1 or 2 wherein said chelating agent is selected from the group of carboxylic acids, polycarboxylic acids, amino carboxylic acids, polyamino polyalkylenephosphonic acids, and salts thereof.

4. The composition of claim 3 wherein said chelating agent is selected from the group of citric acid, EDTA, and diethylene triamine pentamethylene phosphonic acid.

5. The composition of clai 1, 2 or 4 wherein the level of chelating agent is from 0.05% to 0.2%.

6. The composition of claim 1 or 2 wherein the levewl of imidazoline ester is from 15% to 25%.

7. The composition of claim 1 wherein the pH of the composition is from 2.5 to 4.

8. The composition of claim 3 wherein the level of chelating agent is from 0.05% to 0 2%.