CA1118965A - Textile treatment compositions - Google Patents

Abstract

TEXTILE TREATING COMPOSITIONS
J.P.C.I.M. Leclercq P.C.E. Goffinet B.A. Brown ABSTRACT OF THE DISCLOSURE

A textile treating composition in the form of an aqueous dispersion comprises certain substituted polyamine salts and a silicone in a weight ratio of polyamine/silicone of from 5:1 to 1:100. Preferred compositions have a higher alkyl polyamine salt substituted with ethylene oxide groups.
The silicone is preferably a poly-diakyl- or alkylaryl-siloxane and may be substituted with substituens of cationic character. An ease-of-ironing benefit is imparted to fabrics rinsed in dilute solutions of the composition.

Description

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This Application relates to fabric treatment compositions and to a method for treating fabrics in an aqueous bath such as the final rinse after a washing process in order to improve various properties of the fabric. Generally similar composi-tions are disclosed in the co-pending Canadian patent applic-ation Serial No. 257,084 filed on July 15th, 1976 and in the Canadian patent application No. 279,293 filed on May 27, 1977.

It has been known for some years that fabrics can be made to feel softer by treatment in a dilute solution or dispersion of certain cationic quaternary ammonium derivatives and rinse-additive compositions have been marketed for this purpose. The inventions disclosed in the above mentioned British Patent Applications provide substantial additional benefits by a combination of fabric conditioning agents.
These benefits may include some or all of: easier ironing, anti-static properties, pleasanter feel of the fabrics, soil release properties. It appears that recognition of improved "ease of ironing" can arise from a combination of at least three factors, namely fewer wrinkles to be removed, wrinkles more easily removed (e.g. with less weight upon the iron), or more completely removed, and less effort required to slide the iron along the fabric. "Pleasanter" feel can be consis-tently observed by experienced judges, although it is not easy to define in words the sensation or combination of sen-sations they like. Anti-static and soil release properties improve the achieving and maintaining of soil-free fabrics.

The combination of fabric conditioning agents referred to ; above requires the presence of both a cationic quaternary ammonium (or imidazolinium) derivative and a silicone. More specifically the invention described in Canadian S.N.
257,084 provides a textile treating composition which is an aqueous dispersion comprising:
(a) a fabric substantive quaternary ammonium textile softening compound having in its molecular structure èither two alkyl groups each having 12 to 20 carbon atoms or one alkyl chain having 18 to 24 carbon atoms or a fabric substantive quaternary imidazolinium textile softening compound, and (b) a silicone having a cationic character, the weight ratio of component (b) to component (a) being in the range from 20:1 to 1:100.

It is an object of the present invention to provide more effective carrier materials for depositing silicones on fabrics and, in particular, to provide compositions which enable the use of conventional poly-dialkyl siloxanes.

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Accordingly, the present invention provides a tex-tile treating composition which is an aqueous dispersion comprising:
(a) a fabric substantive cationic compound select-ed from the group consisting of i) a subsituted polyamine salt having the formula R' R' R' 2)n 1+ ~ (CH2)n - N+ j- R' A(-) R' R' R' m wherein R and optionally one of the R' groups fix-ed on the same nitrogen atom as R is an alkyl or alkenyl group having 10 to 22 carbon atoms, the other R' groups, which may be the same or dif-ferent, each represent hydrogen or a (C2H4O)pH or a (C3H6O)pH group, or a Cl 3 alkyl group provided that not all represent a Cl 3 alkyl group, where p is a number such that up to 25 (C2H~O) or (C3H6O) groups in all are present, m i5 from 0 to 8, n is from 2 to 6 and A( ) represents one or more anions having total charge balancing that of the nitrogen atoms;
ii) a polyamine salt having the above formula (i) wherein R is hydrogen, or a Cl 4 lower alkyl group, n is from about 2 to 4, preferably 2, and m is not less than 2, preferably from 8 to 16;
iii) or mixtures thereof: and (b) a silicone as hereinafter defined, the weight ratio of component (b) to component (a) being in the range from 5:1 to 1:500.

For the purpose of the present invention a silicone is defined as predominantly linear poly dialkyl or alkyl, aryl siloxane in which the alkyl groups have one to five carbon atoms and may be wholly or partially fluorinated. The silicone will be present in the form of ~n emulsion. This definition also includes silicones of cationic character which can be one of ~he following:
(a) a predominantly linear di Cl-C5 alkyl or Cl-C5 - alkyl, aryl siloxane having a viscosity at 25C of at least 100 centistokes, prepared by emulsion polymerisation using a cationic surfactant as emulsifier;
(b) an a,~-di quaternised di Cl-C5 alkyl or Cl-C5 alkyl, aryl siloxane polymer or (c) an amino-functional~-di Cl-C5 alkyl or alkyl aryl siloxane poly~er in which the amino group may be substituted and may be quaternised and in which the degree of substitution (d.s.) lies in the range 0.001 to 0.1, preferably .01 - 0.075.

A limited degree of cross linking of the siloxane polymer is permissible and up to about 10~ by weight of mono alkyl or mono aryl siloxanes may be present in the sili-cones.
- a) Fabric substantive cationic softening component : Materials suitable as the fabric substantive cat-ionic softening component are as described above.
The compounds (ii) above include protonated poly-ethylene imine derivatives.
Acid salts of diamine compounds, as used herein, are the addition products formed when certain acids add to the amino moieties of the diamines and form mono- or di-ammon-ium salts.

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' ` ' . ' ' ' ' The diamine acid salts can be partially acidified diamine salts (i.e. only one nitrogen quaternized with aeid) of fully acidified diamine salts (i.e. both nitrogen quater-nized with acid).
A variety of acids can be used herein to form the acid salts so long as the anion of the diamine acid salt formed is stable under fabric rinse conditions and is non-interfering in the rinse. Suitable acids include organic and inorganie aeids such as hydrochloric acid, acetic acid, sulphuric aeid, lactrie acid, stearic acid, formic acid, citric acid and a large variety o~ others. Particularly preferred acids used to form diamine acid salts include acetie acid and hydrochloric acid.
Nonlimiting examples of such diamine aeid salts inelude:

(C 6H33 - NH(CH3)-(CH2)3 NH(CH3)2~ 3 2 (cl8H37 - NH(CH3)-(CH2)2~NH(C2H5)2~ ( 3 2 (C H - NH(CH3)-(CH2)3-H2N C12 25~ 2 (C12H25 ~ NH(C2H5)-(CH2)3 NH(C3H7)2~ 3 4 2 ~ allow H2 (cH2)3-NH(c2H5)2) Br2 2oH4l-NH(cH3)-(cH2)2-NH(cH3)21 2 (C15H31-NH(C2H5) ( 2 3 3 "

~ 18 37 N~2 (CH2)3-~2N-cH3) (HCOO)2 ( 16 33 NH2 (CH2)3-H2N-cl6H33~ ++ C12-NE~(CH3)~(CH2)3~NH(C2H5)2~++ (CH COO) -~cl6H33NH(cH3)-(cH2)5-NH(c2H5)2~ (C 3 4 2 (Cl2H25NH(c2H5)-(cH2)2-NH(c3H7)2~ 2 ~Cl4H29NH(cH3)-(cH2)3-(cH3)NH (C8H17)~ 3 2 wherein in the abo~e formulas RTal1ow is the alk~l group derived from tallow fatty acid.
Other examples of suitable compounds include those in which the starting diamine is N-tetradecyl, N'-propyl-1,3-propane-diamine; N-eicosyl,N,N',N'-triethyl-1,2-ethane- -diamine and N-octadecyl,N,NI,N'-tripropyl-1,3-propane-diamine.
The form in which the diamine acid salt is derived is not critical. The diamine acid salt can be formed from ;
diamines in situ during the preparation of the aqueous fabric conditioning compositions herein or can alter-natively, for example, be obtained as the acid salt from commercial sources (e.g. Duomac~ T marketed by Armour-Hess Co. Mixtures of diamine acid salts can, of course, be used as the static control agent in the compositions of the present invention.
The fully acidified diamine salts (i.e. the diacid salts) are particularly preferred inasmuch as these materials permit formation of highly stable, clear, aqueous liquid fabric conditioning compositions.
Preferred aqueous fabric conditioning compositions contain diamine acid salts of the formula on page 3 wherein R is alkyl of from about 16 to about 18 car-bon atoms; and each R' is the same or different and represents hydrogen or alkyl of from about -: : .
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l to about 2 carbon atoms and n is 2 or 3, more preferably 3.
Diamine acid salts useful in the invention herein are commercially available under a variety of trade names including Duomeens ~ and Duomacs ~ (marketed by Armour-Hess Co.) and Dinozem ~ and Dinoremac ~ (marketed by CECA/Pierre-fitte-Auby). Moreover, tne starting diamine compounds can be prepared in accordance with processes disclosed in the art, as, for example, in U.S. Patent 2,267,205 issued December 23, 1941 to Kyrides and U.S. Patent 2,246,524 issued June 24, 1941 to Kyrides.

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b) Silicone comPonent ~ ~
As mentioned previously, the silicone component is an aqueous emulsion of a predominantly linear polydialkyl or alkyl, aryl siloxane in which the alkyl groups can have from one to five carbon atoms and may be wholly or partially fluorinated. Suitable silicones are polydi-methyl siloxanes having a viscosity at 25C in the range ~rom 100 to 200,~00 centistokes preferably no more than 120,000 centistokes. Fluorinated silicones having a viscosity of at least 100 centistokes are also useful.

The silicone component also embraces silicones of cationic character such as are disclosed in Canadian S.N.
297,293, which can be one of:
(a) a predominantly linear di Cl-C5 alkyl or Cl-C5 alkyl, aryl siloxane having a viscosity at 25C of at least 100 centistokes, prepared by emulsion polymerisation using a cationic surfactant as emulsifier.
(b) an ~ di quaternised di Cl-C5 alkyl or Cl-C5 alkyl, aryl siloxane polymer or (c) an amino-functional di Cl-C5 alkyl or alkyl aryl siloxane polymer in which the amino group may be substituted and may be quaternised and in which the degree of substitution (d.s.) lies in the range 0.001 to 0.1, preferably .01-0.075.

~1 a) Cationic emulsion polymerised siloxanes Cationic emulsion polymerised siloxanes are known in the art and can be prepared by strong alkali or acid catalysis of siloxane monomer(s) in the presence of a cationic emulsifying agent. Hyde and Wehryl US Patent No.2,891,920 describes general procedures for such poly-merisations and Examples 1 - 6 of the patent provide specific teaching of the required reaction conditions.
The siloxane monomer can be any di lower alkyl siloxane such as dimethyl, diethyl dipropyl, or ethyl butyl silox-ane or alkyl, aryl siloxane such as methyl, phenyl silox-ane or ethyl phenyl siloxane. However, the preferred starting material for emulsion polymerisation is normally a eylie trimer or tetramer of the desired siloxane.
The emulsifying agent can be any one of a wide range of cationic surfactants such as:
Aliphatic fatty amines and their derivatives such as dodecylamine acetate, octadecylamine acetate and - ;
aeetates of the amines of tallow fatty acids; homologues of aromatie amines having fatty ehains sueh as dodeeyl-aniline; fatty amides derived from aliphatic diamines sueh as undeeylimidazoline; fatty amines derived from di-substituted amines such as oleylaminodiethylamine;
derivatives of ethylene diamine; quaternary ammonium eompounds sueh as dioetadeeyldimethyl ammonium chloride, didodeeyldimethyl ammonium chloride and dihexadeeyl-dimethyl ammonium chloride; amide derivatives of amino alcohols sueh as ~ -hydroxyethylstearyl-amide; amine salts of long ehain fatty acids; quaternary ammonium bases derived from fatty amides or di-substituted diamin-es sueh as oleylbenzylaminoethylene diethylamine hydro-_ 9 _ .

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chloride; quaternary ammonium bases of the benzimi~azolines such as methylheptadecyl benzimidazol hydrobromide; basic compounds of pyridinium and its derivatives such as cetyl-pyridinium chloride; sulfonium compounds such as octadecyl-sulfonium methyl sulfate; quaternary ammonium compounds of betaine such as betaine compounds of diethylamino acetic acid and octadecylchloromethyl ether; urethanes of ethylene diamine such as the condensation products of stearic acid and diethylene triamine; polyethylene diamines; and poly-propanolpolyethanol amines.
The emulsifier is conventionally employed at alevel of 1% - 10% by weight of the siloxane, more preferably 2% - 5~ by weight.
The catalyst employed to polymerise the siloxane is preferably an alkaline catalyst such as an alkali me,tal hydroxide or a quaternary ammonium hydroxide of the formula (R)4N OH. In such ammonium hydroxides the Rgroups can be hydrogen or alkyl radicals such as methyl, ethyl, propyl, butyl, isobutyl, decyl or octadecyl or aralkyl radicals such as benzyl or hydroxyalkyl radicals such as hydroxyethyl, hydroxypropyl and hydroxybutyl.
Most preferably the catalyst is a quaternary ammonium hydroxide having at least one radical of a least 12 carbon atoms in chain length, such a material also serving as an emulsification agent. Long chain length alkyl quater-nary ammonium salts are also preferred as the emulsification agents, particularly di-long chain alkyl di-lower alkyl quaternaries, such as ditallowyl dimethyl ammonium chloride (~TDMAC), available commercially from Armour Chemical Company as Arquad 2HT (Arquad is a Registered Trade Mark) and imidaz-olinium derivatives such as methyl C18 alkyl amidoethyl, - 10 _ Cl~ alkyl imidazolinium methosulphate, available commercially from Ashland Chemical Company as Varisoft 475 (Varisoft is a Registered Trade Mark).
The level of catalyst usage is dependent on the catalyst type employed. Acid catalysts are conventionally used at high levels, e.g. at 15% or more by weight of the aqueous phase of the emulsion. Alkaline catalysts by con-trast are used at lower levels, eOg. from 0.001~ to 10%, preferably from 0.1% to 5% by weight of the siloxane monomer.
Emulsion polymerisation of dimethyl siloxane using DTDMAC as emulsifier In a typical preparation, dichloro dimethyl siloxane was first hydrolysed to form octamethyl cyclo tetra siloxane using the method of Patnode and Wilcock in JACS 68 1946 pp 358 - 363. 15 grs of this material were then added to a mixture of 131 grs of a 1% aqueous solution of ditallowyl dimethyl ammonium chloride and 3.75 grs of tetrabutyl ammon-ium hydroxide in the form of a 40% aqueous solution. The mixture was stirred during addition of the ingredients by means of a Silverson laboratory emulsifier mixer and, after addition was complete, the reaction mixture was subjected - `
to 15 minutes further agitation using an ultrasonic vibrator.
After 18 hours at 80C poly dimethyl siloxane oil was pre-cipitated from the reaction mixture by addition of 500 mls of ethyl alcohol and was then dried with further alcohol before being heated at 75C under a high vacuum to remove all vol-atile materials. The viscosity of the silicone was deter-mined to be 22,000 centistokes by measurement of its rate of flow under gravity between twa marks on a calibrated tube.
The time taken for a given quantity to flow along the tube was converted to viscosity using a calibration curve estab-lished with commercial silicones of known viscosity. -;~i ' `' ,, . : .

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Using the above-described polymerisation technique, stable 10~ emulsions of polydimethyl siloxane were achieved and equivalent results were obtained when the procedure was repeated using cetyl trimethyl ammonium bromide and the imi-dazoline derivative Varisoft 475 respectively as the emulsifier.

b) a - ~ quaternised polysiloxanes The preparation of ~ , ~ quaternised siloxane polymers can be conveniently carried out using the method disclosed in I.C.I. British Patent Specification No. 1,006,729. In this technique a polysiloxane end-stopped with alkyl halide groups in which the halogen atoms are separated from the nearest silicon atoms by at least three carbon atoms, is reacted with a tertiary amine to give an ~ , ~ -quaternised siloxane polymer. In order to provide the polysiloxane starting material a solution polymerisation is normally carried out to give a polymer of the appropriate molecular weight, and the polymerisation reaction is terminated by reaction with a ~-halo alkyl dimethyl silanol.
As previously stated, the polysiloxane can be a poly di (Cl-C5 alkyl)- or (Cl-C5 alkyl, aryl) siloxane, preferably a polydimethyl siloxane and the tertiary amine can be any alkyl, aryl or mixed alkyl and aryl material.
Examples include trimethyl-amine, cetyl dimethyl-amine, pyridine, phenyl dimethyl-amine.
Preparation of a ~ - ~ dipyridinium polydimethyl siloxane A typical preparation of this class of silicone polymers involved the polymerisation of 23.2 grs of octa-methyl cyclotetra siloxane in the presence of 0.9 mls of ' 30 concentrated sulphuric acid and 2.5 grs of 1,3-bis, 3-chloropropyl tetramethyl disiloxane. The mixture was shaken in a sealed flask for 48 hours at room temperature, following which 5 mls of water were added and the flask shaken for a further hour. The resulting emulsion was split by addition of 50 mls of diethyl ether and the organic layer was than washed twice with 30 ml aliquots of distilled water, dried over sodium bicarbonate and magnesium sulphate and filtered. ~vaporation of the filtrate to remove the ether left 23 grs of a clear oil of viscosity 100 cs. NMR exam-ination of the oil showed it to correspond to a polymer hav-ing 36 siloxane units.
10 grs. of the ~ bis(3 chloropropyl) sili-cone prepared above were then refluxed in 10 mls pyridine for 36 hours at 120~C. Excess pyridine was distilled off under reduced pressure leaving a brown viscous oil. This was then dissolved in toluene, washed with water and the toluene layer dried and evaporated to remove the toluene.
NMR spectral analysis disclosed a level of proton activity corresponding to 70-80% of the theoretical uptake of pyridine.
10% aqueous emulsions of the silicone product were prepared by mechanical emulsification using an ethoxy-20 lated linear alcohol emulsifying agent (Dobanol 45E4, a C14-C15 linear alcohol tetra ethoxylate supplied by Shell Inter-national Chemicals Limited) at a level of 20% by weight of the siloxane.
c) Amino functional linear polysiloxanes Amino functional linear polysiloxanes can be prepared by the general method disclosed in British Patent Specification No. 1,339,906 at page 3 lines 78-108, page 4 lines 1-65 and page 3 lines 3-14. In this method, a hydrosiloxane is reacted with an alkenyl group-containing tertiary amine in the presence of a platinum catalyst in accordance with the equation .
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H2P-tCl (Me3SiO)2 (SiMe20~x(SiMeHO)y + yCH2=CHR'NR2 6 _~
(Me3SiO)2 (SiMe2O)x(OSi(Me)R'' NR2)y wherein x = 10 to 100, y = 1 to 20, R is a methyl, ethyl or phenyl group, R' is a direct linkage or a divalent organic group free of alisphatic unsaturation containing 1-16 carbon atoms and R" is a divalent organic group free of aliphatic unsaturation containing 2-18 carbon atoms.
The product of the above reaction can then be quaternised by further reaction with an alkyl halide or ean be converted to the hydrochloride by acidifieation with hydrochlorie acid.
Preparation of po_ydimethyl siloxane substituted with dimethyl aminopropyl groups In a typical preparation 50 grs of dimethyl-methyl hydrogen siloxane eopolymer containing approximately 76 di-methyl siloxane units and 6 hydromethyl siloxane units was dissolved in 50 mls toluene containing a trace of chlorplat-inie aeid. The mixture was stirred under nitrogen at 80C, 5.18 grs of N,N-dimethylallylamine in 10 mls of toluene was :
added dropwise, holding the reaetion temperature at 80-90C., and the reaetion mixture was stirred for a further 2 hours and then eooled. Sodium earbonate was added to neutralise any remaining aeid and the mixture was filtered and rotary evaporated to remove solvents, leaving a pale yellow fluid of low viscosity. N~R analysis showed the formation of , poly dimethyl siloxane eontaining dimethylaminopropyl groups at a level eorresponding to a reaction eomple-teness of 80%+, and a degree of substitution (d.s.) of 0.06.
20 grs of the reaction product was stirred in 100 mls of a 1:1 mixture of dichloromethane and isopropanol and 1.3 mls of eoneentrated HCl (11.21M) in 10 mls of the same solvent mixture was added slowly at room temperature.

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Following evaporation of the solvent a pale coloured solid was left and NMR analysis showed this material as having a proton ratio close to the expected value for the hydrochloride derivative with no detectable level of t~e starting material.
The siloxane polymer was then made up into a 10% aqueous emulsion using 20% based on the siloxane weight of a nonionic emulsification agent (Dobanol* 45E4, a linear C14-Cl~ alcohol containing 4 moles of ethylene oxide supplied by Shell Inter-national Chemicals Limited).
* Dobanol is a Registered Trade ~lark.
A similar experimental technique to the above was employed to produce polydimethyl siloxanes having respective-ly approximately 40 siloxane units and a d.s. of 0.04 and 72 siloxane units with a d.s. of 0.015.
The concentration of the aqueous dispersions (by which term is included solutions) which constitute the com-positions of the invention is not critical and is controlled by practical considerations. Thus the dispersions should be concentrated enough not to be wasteful in transit costs, 20 yet should be fluid enough to be poured and to disperse readily in a usage bath. Usuallv a content of from about 1% to 20%, especially about 3-10% by weight of components (a) and (b) together is convenient. As stated earlier, the ratio of the siloxane portion of component (b) to the quat-ernary softening agent of component (a) should be in the ratio of 20:1 to 1:100 by weight, preferably from 2:1 to 1:10 and most preferably from 1:1 to 1:5.
The aqueous dispersions may contain other components, such as emulsifying aids, for instance low levels of the order of about 1% by weight of nonionic surfactants to aid dispersion of the usually poorly soluble cationic softeners.

, i , A wide range of nonionic emulsifiers can be used for this purpose such as those disclosed in German Patent Application OLS 2500111 published July 17th, 1975. It is found that use of emulsifiers is sometimes desirable to aid also the dis-persion of the silicones in the compositions of the invent-ion, especially when silicones of relatively high viscosity are employed.
Highly preferred optional ingredients also include nonionic fabric treatment agents such as the fatty acid partial esters of mono- or polyhydric alcohols or anhydrides thereof having from 1 to about 8 carbon atoms in the alcohol.
In these compounds the fatty acid ester should have at least 1, more preferably at least 2, fatty acyl groups.
The alcohol portion of the ester can be ethylene glycol, glycerol, diglycerol, xylitol, sucrose, erythritol , pentaerythritol, sorbitol or sorbitan; sorbitan esters are particularly preferred.

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The fatty acid portion of the ester normally comprises a fatty acid having from 12 to 22 carbon atoms, typical examples being lauric acid, myristic acid, palmitic acid, stearic acid and behenic acid.
Amongst these esters, the most preferred are the glyceryl esters of stearic acid, especially glyceryl monostearate, and the sorbitan fatty acid esters, which are esterified dehydration products of sorbitol.
These sorbitan fatty acid esters are disclosed in Canadian Patent 1,074,965. Nonionic fabric conditioning materials of this type are commonly employed at levels of 1 - 5% preferably 2 - 4% by weight of the composition.
Other preferred ingredients include pyrodextrins such as British Gum and White dextrin and substituted dextrins such as dextrin phosphates, cationic dextrins and dextrin pyrollidone carboxylic acid, in which the degree of substitution is from 0.01 to 2.0 preferably 0.05 to 1.5. A preferred cationic dextrin is a white dextrin that has been reacted with glycidyl `
trimethyl ammonium chloride to provide a degree of substitu-2Q tion (d.s.) in the dextrin molecule of from about 0.1 to 1Ø
The dextrins are used at levels of 0.5% to 5% by weight of the compositions, preferably at levels of 1% to 3%.
Non-aqueous, water miscible solvents may be present, and other viscosity controlling agents, such as low levels of electrolytes. Other optional components include appropriate optical brighteners, fungicides and germicides, colouring or ~`~
opacifying agents, and perfumes.
In use the compositions of the invention are normally incorporated in an aqueous bath containing the ingredients of 3Q the compositions in the ratios defined hereinabove, at a con-centration such that there is present from about 20 to 1,000 parts per million by weight of components (a) and (b) together of which at least 10 ppm is component (b). Preferably the bath ",. ~

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contains from about 50 to 200 ppm of components (a) and (b)together of which at least about 15 to 150 ppm is component (b).
The invention also embraces a method of treating textile and textiles when so treated, which method comprises steeping them in such a bath.
The textiles may be steeped in such a bath and then dried on any occasion, but it is envisaged that normally the treatment will constitute the final rinse after a wash-ing process.
EXAMPLES
Test Procedures Clean test pieces of cotton or other fabric were treated in a domestic washing machine. Either a whole standard load was made up of test pieces or additional clean fabrics were used to make up the load. The machine cycle was set so that the load was subjected to gentle agitation (as for a wool wash cycle) for about 20 minutes in a solution of the test product in water, and was then spin-dried.
Wrinkling test Treated test pieces were compared with a standard set of 10 plastic simulated test pieces of different degrees of wrinkling (American Association of Textile Chemists and Colourists - Three dimensional durable press replicas for use with AATCC Test 124). Number 10 graded perfect, Number 1 worst. A grade 5-7 was deemed to represent about that degree of freedom from wrinkling at which a housewife might be expected to consider ironing unnecessary.

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Ease of Ironing test This was judged by a panel of judges, employing a Scheffe analysis to provide gradings (panel score units -psu) and a "yardstick", i.e. least dif~erence significant at 95% probability.
Ena Result test A visual preference, graded as above in psu.
Softness test A tactile preference, graded as above in psu.
Drying of Fabrics The "spin-dried" test pieces were dried by hanging in the laboratory (static drying) or in a tumbler dryer.
A number of compositions in accordance with the invention were made up and tested for ease of ironing, wrinkle grade, ironed end result and softness, using a commercially available fabric softening product containing 5O8% di-tallowyl dimethyl ammonium chloride as the standard.
Positive figures denote an advantage for the test product and vice versa. An asterisk denotes a significant differ-ence at the 95% level of confidence.

Formulation Levels N-tallowyl, N-methyl N'dimethyl -1,3-propane diamine hydroacetate 4 4 4 N-tallowyl, N-methyl N'dimethyl - -1,3-propane diamine hydrochloride 4 4 Glyceryl monostearate 2 2 2 2.5 4.5 Releasil~ (anonionic emulsified 30 polydimethyl siloxane of viscosity 3 100 cs) available from Dow Corning 2 2 2 2 1.5 Unmodified White Dextrin 3~01 ... ,~.~ .. .. ... . , , ,, ~ , Cationic pyro dextrin 2,92 Ease of ironing +0.78* + .82* +1.2* 1.2* +0.92*
Wrinkling +0.32* +n . 04 -0.3* +0.28 +0.02 Ironed end result-0.10 -0.26*+0.3* +0.22*
Softness +0.3 +0.56* -~1.24*

1. White dextrin supplied by Remy, Belgium.
- 2. Reaction product of glycidyl trimethyl ammonium chloride with white dextrin to give a d.s. of 0.85.
3. Q2-1070 - A nonionic emulsified polydimethyl siloxane of viscosity 350 cs available from Dow Corning.
It can be seen that the compositions of the inven-tion provide an improvement in ease of ironing and, with one exception, an improvement in wrinkle grade of the fabrics prior to ironing, and in ironed end result. Softness of the treated fabrics was also enhanced in those instances where this variable was measured~

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Claims (11)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A textile treating composition in the form of an aqueous dispersion comprising (a) a fabric substantive cationic compound selected from the group consisting of i) a substituted polyamine salt having the formula wherein R is an alkyl or alkenyl group having 10 to 22 carbon atoms, the R' groups are the same or different, and each represents hydrogen or a (C2H40)pH or a (C3H60)pH group, or a C1-3 alkyl group provided that not all represent a C1-3 alkyl group, where p is a number such that up to 25 (C2H40) or (C3H60) groups in all are present, or one of the R' groups fixed on the same nitrogen atom as R is an alkyl or alkenyl group having 10 to 22 carbon atoms, m is from O to 8, n is from 2 to 6 and A(-) represents one or more anions having total charge balancing that of the nitrogen atoms;
ii) a polyamine salt having the formula wherein R is hydrogen or a C1-4 lower alkyl group, R' and A(-) have the above meanings, n' is from about 2 to 4, and m' is not less than 2, iii) or mixtures thereof; and b) as a silicone component a predominantly linear polydialkyl or alkyl, aryl siloxane in which the alkyl groups have one to five carbon atoms or such alkyl groups at least partially fluorinated, the weight ratio of component (b) to component (a) being in the range from 5:1 to l:500.

2. A textile treating composition in accordance with claim 1 wherein the silicone is a silicone of cationic character selected from (a) a predominantly linear di C1-C5 alkyl or C1-C5 alkyl, aryl siloxane having a viscosity at 25°C of at least 100 centistokes, prepared by emulsion polymerisation using a cationic surfactant as emulsifier;
(b) an .alpha.,.omega.-di quaternised di C1-C5 alkyl or C1-C5 alkyl, aryl siloxane polymer or (c) an amino-functional di C1-C5 alkyl or alkyl aryl siloxane polymer in which the amino group may be substitu-ted and may be quaternised and in which the degree of substitution (d.s.) lies in the range 0.001 to 0.1.

3. A textile treating compositing in accordance with claim 1 wherein the weight ratio of the polysiloxane of component (b) to component (a) is in the range 2:1 to 1:10.

4. A textile treating composition in accordance with claim 1, 2 or 3 wherein the silicone component is a nonionic emulsified linear polydimethyl siloxane of viscosity at least 100 centistokes.

5. A textile treating composition in accordance with claim 1 also including a nonionic fabric conditioning agent.

6. A textile treating composition in accordance with claim 5 wherein the fabric conditioning agent is a partial fatty acid ester of a polyhydric alcohol.

7. A textile treating composition in accordance with claim 5 or 6 wherein the fabric conditioning agent is glyceryl monostearate.

8. A textile treating composition in accordance with claim 1 including a pyrodextrin.

9. A textile treating composition in accordance with claim 8 wherein the pyrodextrin is a modified pyrodextrin.

10. A textile treating composition as claimed in claim 9 wherein the modified pyrodextrin is a cationic dextrin.

11. A textile treating composition as claimed in claim 1 wherein the polyamine salt (ii) is one in which R is hydrogen or a C1-C4 lower alkyl group, n' is 2 and m' is from 8 to 16.