CA2179267A1 - Gemini polyhydroxy fatty acid amides - Google Patents

Abstract

Novel gemini polyhydroxy fatty acid amide compounds having formula (I), wherein: X is a bridging group having from 2 to 200 atoms; Z and Z' are the same or different alcohol-containing moieties having two or more hydroxyl groups, or one of Z or Z' is hydrogen; and R and R' are the same or different hydrocarbyl moieties having from 1 to 21 carbon atoms and can be saturated, branched or unsaturated and mixtures thereof. Laundry, cleaning, fabric and personal care compositions comprising these compounds.

Description

~ wo 95~19953 ~ 1 7 9 2 6 7 . ~ /66 GEMINI POLYHYDROXY FATTY ACID AMIDES

TECEINICAL FIBI,D
The present invention relates to gemini polyhydroxy fatty acid amide 10 :u~-rv~ This inYention also relates to laundry, cleaning, fabric and personal care '----r ' comprisingthese~ u~..,.l~
BACKGROUND OF TFTF.lNVF~TlON
The ru-ll-ul~iiull of detergent cu~ presents a ..-,.. l "1~1~ challenge, since effective ~ are required to remove a variety of soils and stains from 15 diverse substrates. In particular, the removal of greasy/oily soils quickly and efficiently can be ulubl~ ic. While a review of the literature would seem to indicate that a wide selection of surfactants is available to the detergent ur~ ulcl, the hality is that many such materials are specialty chemicals which are not suitable in low unit cost items such as home-use detergent ~,,.,1,~ ~;l;,...~ The 20 fact remains that most home-use detergents still comprise one or more of the ~,UII~ ;Ui~al ethoxylated nonionic and sulfated or sulfonated anionic surfactants, ~n~ u~ly due to economic c UII~;I.,.dl;U~
The challenge to the detergent ~ urlL~,~UI~I seeking improved fabric cleaning has been increased by various ~ ;IUIIIII~ dl factors. For example, some 25 llullb;Od~,~lrLI~ ingredients have fallen into disfavor. Effective phosphate builders have been banned by legislation in many countries Moreover, many surfactants areoften available only from l~ulll~ lblt resources such as ~ u-,l~ h,.-ls Accordingly, the detergent, r C:l iS quite limited in the selection of surfactants which are effective cleaners, I:iOd~,.~drl,l~ and, to the extent possible, 30 available from renewable resources such as natural fats and oils, rather than Cu~;d~.~le attention has lately been directed to nonionic surfactants which can be prepared using mainly renewable resources, such as fatty esters and sugars.
One such class of surfactants includes the N-alkyl polyl~ u~ fatty acid amides.
35 Moreover, the ~ of such nonionic surfactants with ~u~ L;u~l anionic surfactants such as the alkyl sulfates, alkyl benzene sulfonates, alkyl ether sulfates, and the like has also been studied. Indeed, substantial success in the ~ ., of wo95/19953 r~l,.J., ' ,66 21 7g267 2 d; ,llwa,LIll~. ~.v.~ .c has recently been achieved using the N-alkyl pul~ lluAyfatty acid amides. However, even these superior surfactants do suffer from some drawbacks. For example, their solubility is not as high as might be desired for optimal .~ ' and this is ~Aau~llJd~cd at chain lengths of about C 16 and above.
s At high ucn~ aLiu..~ in water they can be difficult to handle and pump, so additives must be employed in ~ lufac.~ul;llg plants to control their viscosity While quite compatlble with anionic ~Illf~t~ntc, their ~ y can be diminished "1~ in the presence of water hardness cations. And, of course, there is always the objective to find new surfactants wbich lower interfacial tensions to an 10 even greater degree than the N-alkyl polyhydroxy fatty acid amides at low telllLJ~,.aLul ,~ in order to increase cleaning p~,rul 111~
The present invention gemini polyl.ydluAy fatty acid amide .. 1,.. ,.1~ have been found to be versatile materials useful in a variety of cleaning uulll~Ju~;Li~
especially as sur~actants for use therein.
BACKGROUND ART
Japanese Kokai HEI 3[199L]-246265 Osamu Tachizawa, U.S Patents 5,194,639, 5,174,927 and 5,188,769 and WO 9,206,171, 9,206,151, 9,206,150 and 9,205,764 relate to various polyhydroxy fatty acid amide surfactants and uses thereof.
SUMM~RY OF TH:E~ rNVENTrON
The present invention relates to novel gemini polJ~,~dluAy fatty acid amide .u.. l~ having the formula:
N--X--N
O=C C=O
R R' 2s wherein: X is a bridging group having from about 2 to about 200 atoms; Z and Z' are the same or different alcohol-containing moieties having two or more hydroxyl groups (e.g., glycerol, and units derived from reducing sugars such as glucose, maltose and the like), or one of Z or Z' is hydrogen; and R and R' are the same or different l~ylluudl~yl 3~ moieties having from about I to about 21 carbon atoms and can be saturated, branched or I a~cd (e.g., oleoyl) and mixtures thereof.
The present invention also relates to . ~
(a) at least about 0.1% of a gemini pulyh.~d-uAy fatty acid amide compound WO95/~9953 F~ll-J.. ,~. 166 217~2~7 as described h~ , and (b) at least about 0.1% of one or more laundry or personal care u~l I ;., materials.
The invention aiso provides a method for laundering fabrics or cleaning hard s surfaces, comprising contacting said fabrics or hard surfaces with an aqueous solution containing at ieast about 10 ppm, preferably about 100 ppm-10,000 ppm, of a gemini pGlyi~ i. UAy fatty acid amide compound, preferably with agitation.
Ail p.,..,.,~ , ratios and ~ u~liù..~ herein are by weight, uniess otherwise specified. Ail documents cited are ;Il~,ùllJula~td herein by reference.
Iû DET~TT.l~n DEscp~nTroN 0~ T~ rNYE~TION
1. Gemini rc~lYlly~ Y Fatty Acid ~ C~mnounds:
The present invention c~ ,o~ are gemini pc,l~hy~i.u,.y fatty acid amides having the formula:
Z
N--X--N
O=C C=O
R R' wherein: X is a bridging group having from about 2 to about 200 atoms; Z and Z' are the same or different alcohol-containing moieties having two or more hydroxyl groups (e.g., glycerol, and units derived from reducing sugars such as glucose, maltose and the 20 iike), or either one (but not both) of Z or Z' is hydrogen; and R and R' are the same or different hydrocarbyl moieties having from about I to about 21 carbon atoms and can be saturated, branched or, ~ (e.g., oleoyl) and mixtures thereof.
Preferred X are selected from the group consisting of substituted or , branched or linear ali~yl, ether alicyl, amino aikyl, or amido aii~cyl moieties 2s having from about 2 to about 15 carbon atoms. Preferred alicyl moieties are ....~l~lil..l~d, linear alicyl moieties having the fûrmula -(C~2)n-, whereirl n is an integer from 2 to about 15, preferably from 2 to about 10, and most preferably from 2 to about 6; and also I . .~ , branched alicyl moieties having from 3 to about 15carbon atoms, preferably from 3 to about 10 carbon atoms, and most preferably from 3 30 to about 6 carbon atoms. Most preferred are ethylene and propylene (branched or iinear) alicyl moieties. Aiso preferred are I ' 1, branched or linear ether alicyl moieties having the formula -R2-(O-R2)m-, wherein each R2 is i...l~ ly selected fi-om C2-Cg branched or linear alkyl and/or aryl moieties (preferably ethyl, propyl or W09S119953 r~ u..,s,. /66 ~1792~7 4 "~ thereof) and m is an integer from I to about 5. X may also be , branched or linear amino and/or amido alkyl moieties having the formula -R2-(N(R3)-R2)m-, wherein each R2 ;5; l- ~.. ~. ~lly selected from C2-Cg branched or iinear alkyl and/or aryl moieties (preferably ethyl, propyl or .,....ll.,. -~;".,~ thereof), m s is an integer from l to about 5, and R3 is selected from hydrogen, Cl-Cs alkyl, and -C(o)R4-, wherein R4 is Cl-C21 aikyl, including -C(O)R. The X moiety may be derived from ~,U~I.. ,. ~,;dlly available amine .,u,.. l,ùu.. ~i~ such as, for example, JeffaminesR (supplied by Texaco) such as JED600, JEDRI48, JEDRI92, JED230, lED2000, J-D230 and J-D400.
o Preferred X moieties therefore include: -(CH2)2-. -(CH2)3-. -(CH2)4-. -(CH2)5-, -(CH2)6-, -cH2cH(cH3)(cH2)3 -, -(CH2)2-0-(CH2)2-, -(CH2)3 -O-(CH2)3 -, -(CH2)2-0-(CH2)3 -, -(cH2)2-o-(cH2)2-o-(cH2)2-~ -(CH2)3 -0-(CH2)2-O-(CH2)3-, -(CH2)2-O-(CH2)3 -o-(cH2)2-~ -(CH2)2-NH-(CH2)2-. -(CH2)3 -NH-(CH2)3-, -(CH2)2-NH-(CH2)3-, -(CH2)2-N(C(O)R)-(CH2)2-, -(CH2)3-N(C(O)R, )-(CH2)3-, -(cH2)2-N(c(o)R)-(cH2)3-~ -(CH2)2-NH(C6H4)NH-(CH2)2-~ -(CH2)3-NH(C6H4)NH-(CH2)3-. -(cH2)2-NHcH2(c6H4)cH2NH-(cH2)2-~ -(CH2)3 -NHCH2(C6H4)CH2NH-(CH2)3-, etc.
Preferred Z and Z' are ;~ ly selected from the group consisting of pol;hJJ~u~ JJ~uua.iJyl moiety having a linear l~ u~ b,~l chain with at least 2 hydroxyl (in the case of glycerol) or at least 3 hydroxyls ( in the case of other sugars) directly connected to the chain, or an alkoxylated derivative (preferably ethoxylated or ~.,ul,v~ t~,;i) thereo Z and Z' preferably will be derived from a reducing sugar, more preferably Z and/or Z' is a giycityl moiety. Suitable reducing sugars include glucose, fructose, maltose, lactose, gaiactose, mannose, and xylose, as well as glyceraldehyde.
2s As raw materials, high dextrose corn syrup, high fructose corn syrup, and high maitose corn syrup can be utilized as well as the individual sugars listed above. These corn syrups may yield a mix of sugar . l. .l.u- l~ for Z and Z'. It should be understood that it is by no means intended to exclude other suitable raw materials. Z and/or Z' preferably will be selected from the group consisting of -CH2-(CHOH)-p-CH2OH, -CH(CH2OH)-(CHOH)p l-CH2OH, -CH2-(CHOH)2(CHORl)(CHOH)-CH2OH, where p is an integer from I to 5, inclusive, and Rl is H or a cyclic mono- or pu,~ ' ', and alkoxylated derivatives thereof Most preferred are glycityls wherein p is 4, particularly -CH2-(CHOH)4-CH2OH.
Preferred R and R' are ;.\.l. ~....~1..~lly selected from the group consisting of C3-3s C21 hJJlu~ yl moiety, preferably straight or branched chain C3-C13 alkyl or alkenyl, more preferably straight chain Cs-Cl I alkyl or alkenyl, most preferably straight chain Cs-Cg alkyl or aikenyl, or mixtures thereo R-CO-Nc and/or R'-CO-N< can be, for WO 95/19953 r~ 3~ 166

2~.7g2~7 . 5 ~
example, cocamide, stearamide, oleamide, lauramide, Illyl ;~I.. ud~ lc, r ~, Idllu.. ~e, etc.
Examples of ~O~ J~ according to the present invention therefore include, but are not limited to: CH3(cH2)6c(o)N[cH2(cHoH)4cH2oE~l-(cH2)2 S [CH2(CHOH)4CH20H]NC(O)(CH2)6CH3;
CH3(CH2)8C(O)N[CH2(CHOH)4CH20H]-(cH2)2 [CH2(CHOH)4CH20H]NC(O)(CH2)8CH3;
CH3(cH2)loc(o)N[cH2(cHoH)4cH2oH]-(cH2)2 [CH2(CHOH)4CH2OH]NC(O)(CH2) 1 oCH3;
CH3(cH2)8c(o)N[cH2(cHoH)4cH2oH]-(cH2)2-o-(cH2)2-o-(cH2)2 [CH2(CHOH)4CH20H]NC(O)(CH2)8CH3;
CH3(CH2)8C(O)N[CH2(CHOH)4CH20H]-CH2cH(cH3)(cH2)3 [CH2(CHOH)4CH20H]NC(O)(CH2)8CH3;
CH3(CH2)8C(O)N[CH2(CHOH)4CH20H]-(cH2)3-o-(cH2)2-o-(cH2~3 [CH2(CHOH)4CH20H]NC(O)(CH2)8CH3;
CH3(CH2)3CH(CH2CH3)C(O)N[CH2(CHOH)4CH20H]-(cH2)2 [CH2(CHOH)4CH2OH]NC(O)CH(CH2CH3)(CH2)3 CH3;
CH3(CH2)6C(O)N[CH2(CHOH)4CH20H]-(CH2)3-0-(CH2)2-o-(cH2)3 [cH2(cHoH)4cH2oH]Nc(o)(cH2)6cH3;
CH3(cH2)4c(o)N[cH2(cHoH)4cH2oH]-(cH2)3-o-(cH2)2-o-(cH2)3-[CH2(CHOH)4CH20H]NC(O)(CH2)8CH3; C6H5C(O)N[CH2(CHOH~4CH20H]-(CH2)3-0-(CH2)2-0-(CH2)3-[CH2(CHOH)4CH20H]NC(O)C6H5;
CH3(CH2)4C(O)N[cH2(cHOH)4cH2oH]-(cH2)2 [CH2(CHOH)4CH20H]NC(O)(CH2)8CH3 .
These ~ u~ can be readily ~ from the following disugar diamines: HN[CH2(CHOH)4CH2OH]-(CH2)2-[CH2(CHOH)4CH2OH]NH;
HN[CH2(CHOH)4CH20H]-CH2CH(CH3)(CH2)3-[CH2(CHOH)4CH20HlNH;
HN[CH2(CHOH)4cH20H] -(CH2)2-0-(CH2)2-0-(CH2)2-[CH2(CHOE~)4CH20H]NH; HN[CH2(CHOH)4CH20H]-(CH2)3-0-(CH2)2-(CH2)3-[CH2(CHOH)4CH20H]NH, and HN[CH2(CHOH)4CH20Eq-(CH2)3-[CH2(CHOH)4CH20H]NH.
2. C~ )ci~
ln addition to comprising at least about 0.1% of a gemin; pul~ dluu~y fatty acidamide compound as described II.,.t;llb~.C'Ule, the present invention c.~ further35 comprise at least about 0.1% of one or more laundry or personal care materials. Such materials useful in laundry or personal care products cr~ ~,.u, include the following WO 9S/19953 . r~ . . IC6 ~
~17~2~7 6 (a) ~ - Enzymes can be included in the r~..,...,l-~;....~ herein for a wide varjety of fabric laundering purposes, including removal of protein-based.
.,~ubotyll~e-based, or l~ l;dc-based stains, for example7 and for the preventionof refugee dye transfer, and for fabric restoration. The enzymes to be i~,ul~JUl~lL~
s include proteases, amylases, lipases, cellulases, and p~,.u~d.kl~.~, as well as mixtures thereo Other types of enzymes may also be included. They may be of any suitableorigin, such as vegetable, animal, bacterial, fungal and yeast origin. However, their choice is governed by several &ctors such as pH-activity and/or stability optima, ~h... - ' ' .y, stability versus active detergents, builders and so on. In this respect 10 bacterial or rungal enzymes are preferred, such as bacterial amylases and proteases, and fungal cellulases.
Enzymes are normally i....v.~,u.~Ltd at levels sufficient to provide up to about5 mg by weight, more typically about 0 01 mg to about 3 mg, of active enzyme pergram of the ~ o~:l;",. Stated otherwise, the c.c,.. ~ herein will typically comprise from about 0.001% to about 5%, preferably 0.01%-1% by weight of a ..;~1 enzyme preparation. Protease enzymes are usually present in such CC,Ilull~ll,;al ~J.t~ L;C,..~ at levels sufficient to provide from 0.005 to 0.1 Anson units (AU) of activity per gram of c Suitable examples of proteases are the subtilisins which are obtained from particular strains of B.subtilis and B.l;~ .urull~la. Another suitable protease is obtained from a strain of Bacillus, having maximum activity throughout the pH range of 8-12, developed and sold by Novo Industries A/S under the registered trade name ESPERASE. The preparation of this enzyme and analogous enzymes is described in British Patent ~p~orifirgtir,n No. 1,243,784 of Novo. Proteolytic enzymes suitable for 2s removing protein-based stains that are .,u."l.l~ y available include those sold under the tradenames ALCALASE and SAVINASE by Novo Industries A/S
(Denmark) and MAXATASE by IllLelll~;oll.d Bio-Synthetics, Inc. (The lllda). Other proteases include Protease A (see European Patent Application 130,756, published January 9, 1985) and Protease B (see European Patent Application Serial No. 87303761.8, filed April 2rS, 1987, and European Patent Application 130,756, Bott et al, published January 9, 1985).
Amylases include, for example, o~-amylases described in British Patent Sl, ~ J \ No. 1,296,839 (Novo), RAPIDASE, l. -. ., A~ Bio-Synthetics, Inc.
and TERMAMYL, Novo Industries.
The cellulase usable in the present invention include both bacterial or fungal cellulase. Preferably, they will have a pH optimum of between S and 9.5. Suitable cellulases are disclosed in U.S. Patent 4,435,307, Barbesgoard et al, issued March 6, W0 95119953 ~1~ 9 2 6 7 F~I~ C - I66 1984, which discloses fungal cellulase produced from Humicola insolens and Humicola strain DSM1800 or a cellulase 212-producing fungus belonging to the genus Aeromonas, and cellulase extracted from the ll l/A~opAl l~aS of a marine mollusk (Dolabella Auricula Solander). Suitable cellulases are also disclosed in GB-s A-2.075.028; GB-A-2.095.275 and DE-OS-2.247.832.
Suitable lipase enzymes for detergent usage include those produced by UUI~;a~ of the rS~ group, such as rS~ stutzeri ATCC
19.154, as disclosed in British Patent 1,372,034. See also lipases in Japanese Patent Application 53,20487, laid open to public inspection on February 24, 1978. This 0 lipase is available from Amano Pllall,.a~,e~-Li-,cl Co. Ltd., Nagoya, Japan, under the trade name Lipase P "Amano," hereinafter referred to as "Amano-P." Other commercial lipases include Amano-CES, lipases ex Cluullluba~,Lel viscosum, e.g.
Cluulll~a~,~el viscosum var. Iipolyticum NRRLB 3673, cu.. ", "~, available from Toyo Jozo Co., Tagata, Japan; and further cluullluba~Lel viscosum lipases from U.S, 5 P~ rhPr~ Corp., U.S.A. and Disoynth Co., The N~ , and lipases ex P~ , gladioli. The LIPOLASE enzyme derived from Humicola lanuginosa and cc,..~...,., ".~, available from Novo (see also EPO 341,947) is a preferred lipase for use herein.
Peroxidase enzymes are used in ~ ;o~. with oxygen sources, e.g., 20 p.,,~ lbullaLe, perborate, persulfate, hydrogen peroxide, etc. They are used for "solution bleaching," i.e. to prevent transfer of dyes or pigments removed from substrates during wash operations to other substrates in the wash solution.
Peroxidase enzymes are known in the art, and include, for example, horseradish peroxidase, ligninase, and l.&10~u~,~u~iJa~c such as chloro- and bromo-peroxidase.
2s Peroxidase-containing detergent ~ are disclosed, for example, in PCT
r..,., ~;"" 1 Application WO 89/099813, published October 19, 1989, by O. Kirk, assigned to Novo Industries A/S.
A wide range of enzyme materials and means for their illCul~ul~lliu~l into synthetic detergent: . are also disclosed in U.S. Patent 3,553,139, issued January 5, 1971 to McCarty et al. Enzymes are further disclosed in U.S. Patent 4,101,457, Place et al, issued July 18, 1978, and in U.S. Patent 4,507,219, Hughes, issued March 26, 1985, both. Enzyme materials useful for liquid detergent r.,.,...,l-~ c~ and their ~,ul~iull into such r.,.... ~ , are disclosed in U.S.
Patent 4,261,868, Hora et al, issued April 14, 1981. Enzymes for use in detergents 3s can be stabilized by various techniques. Enzyme - ' " techniques are disclosed and ,"~ ' in U.S. Patent 3,600,319, issued August 17, 1971 to Gedge, et al, and European Patent Application Publication No. 0 199 405, wo 95119953 . r~ J66 ~17~267 8 Application No. 86200586.5, published October 29, 1986, Venegas. Enzyme 1 ' systems are also described, for example, in U.S. Patent 3,519,570.
(b) Enzyme Stabilizers - The enzymes employed herein are stabilized by the presence of water-soluble sources of calcium and/or magnesium ions in the finished s c. .~ which provide such ions to the enzymes. (Calcium ions are generally somewhat more effective than magnesium ions and are preferred herein if only onetype of cation is being used.) Additional stability can be provided by the presence of various other art-disclosed stabilizers, especially borate species: see Severson, U.S.
4,537,706. Typical detergents, especially liquids, will comprise firom about I to 0 about 30, preferably firom about 2 to about 20, more preferably from about 5 to about 15, and most preferably from about 8 to about 12, millimoles of calcium ion per liter of finished ~ This can vary somewhat, depending on the amount of enzyme present and its response to the calcium or magnesium ions. The level of caAcium or magnesium ions should be selected so that there is always some minimum level available for the enzyme, after allowing for ~ ;./ with builders, fatty acids, etc., in the ~ Any water-soluble calcium or magnesium salt can be used as the source of calcium or magnesium ions, including, but not limited to, calcium chloride, calcium sulfate, calcium malate, calcium maleate, calcium hydroxide, calcium fommate, and calcium acetate, and the cu..c~yul,1;.,~ magnesium 20 salts. A small amount of calcium ion, generally from about û.û5 to about 0.4 millimoles per liter, is often also present in the ~ J"'I ''`;l;"" due to calcium in the enzyrne slurry and fommula water. In solid detergent .. ,~ the ru".,~Jk"iu..
may include a sufficient quantity of a water-soluble calcium ion source to provide such amounts in the laundry liquor. In the altemative, natural water hardness may 2s suffice.
It is to be understood that the foregoing levels of calcium and/or magnesium ions are sufficient to provide enzyme stability. More calcium and/or magnesium ions can be added to the ~ u ~ ;. . c to provide an additional measure of grease removal 1,, ~ Accordingly, as a general proposition the ~ herein will 30 typically comprise from about 0.05% to about 2% by weight of a water-soluble source of calcium or magnesium ions, or both. The amount can vary, of course, with the amount and type of enzyme employed in the c.. 1.~:l ;....
The c~ u~ - herein may also optionally, but preferably, contain various additional stabilizers, especially borate-type stabilizers. Typically, such stabilizers 3s will be used at levels in the ~ ;u ~ from about 0.25% to about 10%, preferably from about 0.5% to about 5%, more preferably from about 0.75% to about 3%, by weight of boric acid or other borate compound capable of fomling boric acid in the wo 95119953 2i 1 '1 g ~ 6C

~.u l ,u~ (calculated on the basis of boric acid). Boric acid is preferred, although other .,o".puu..~s such as boric oxide, borax and other alkali metal borates (e.g., sodium ortho-, meta- and pyroborate, and sodium p ~ ..Alr) are suitable.
Substituted boric acids (e.g., ~uh.,..Jl~u~u~lu acid, butane boronic acidl and p-bromo s ; ' , ~u~ u~f~. acid) can also be used in place of boric acid.
(C) R~ `hir~ Compounds pl~arhir~ A~ents and RI~ h ACtiVAtnrs ~ The detergent ~ herein may optionally contain bleaching agents or bleaching .u ~ containing a bleaching agent and one or more bleach activators. When present, bleaching sgents will typically be at levds of from about 1% to about 30%, o more typically from about 5% to about 20%, of the detergent ~ ;. , especially for fabric laundering. If present, the amount of bleach activators will typically be from about 0.1% to abûut 60%, more typically from about 0.5% to about 40% of thebleaching ~ comprising the bleaching agent-plus-bleach activator.
The bleaching agents used herein can be any of the bleaching agents usefiul for s detergent .~ ,l.o~ in textile cleaning, hard su&ce cleaning, or other cleaningpurposes that are now known or become known. These include oxygen bleaches as well as other bleaching agents. Perborate bleaches, e.g., sodium perborate (e.g., mono- or tetra-hydrate) can be used herein.
Another category of bleaching agent that can be used without restriction 20 . ."~ p...u~buA~l;c acid bleaching agents and salts thereo Suitable examples of this class of agents include m-A~n~ci-lm l-lOllO,C~.u~y~l,LI.~ e l.."...l.yd~_le, the magnesium salt of metachloro perbenzoic acid, 4-nu.l~1~1.,.,.~-4-U~uy~,.U~U~yllU acid and d;~.u~y~lo~ acid. Such bleaching agents are disclosed in U.S. Patent 4,483,781, Hartman, issued November 20, 1984, U.S.
2s Patent Application 740,446, Burns et al, filed June 3, 1985, European Patent Application û,133,354, Banks et al, published February 2û, 1985, and U.S. Patent4,412,934, Chung et al, issued November 1, 1983. Highly preferred bleaching agents also include 6-l~ully' 6-u~ul~.,.u~ lo;u acid as described in U.S. Patent 4,634,551, issued January 6, 1987 to Burns et al.
Peroxygen bleaching agents can also be used. Suitable peroxygen bleaching ,,,,,,~.. ~.. lc include sodium carbonate ~.,.u~yl~ c and equivalent "~ .. I,u.. ~"
bleaches, sodium IJJ.uyllOa~ lc ~.,.u~yl~d~_lc, urea ~.u~l~yd~_Lc, and sodium peroxide. Persulfate bleach (e.g., OXONE, .. ~.,uL.,~ulcd cu.. ~.u;.. lly by DuPont) can aAso be used.
3s A preferred p.,.c. .I,u.. lt~, bleach comprises dry particles having an average particle size in the range from about 500 lllh,lulll.,tcl~ to about 1,000 Illl~lUIII.,t~
not more than about lû% by weight of said particles being smaller than about Z00 WO 95119953 ~ 1 ~ 9 2 6 7 ~ 766 ~

llfi~lull..,t~.~ and not more than about 10% by weight of said particles being larger than about 1,250 IlULlUlllCt..~. Optionally, the ~.L~ L~ can be coated with silicate, borate or water-soluble surfactants. rc~l,a~u~ld~c is available from vârious commercial sources such as FMC, Solvay and Tokai Denka.
s Mixtures of bleaching agents can also be used.
Peroxygen bleaching agents, the perborates, the p~,~u~ orl~ca~ etc., are preferably combined with bleach activators, which lead to the In si~u production in aqueous solution (i e., during the washing process) of the peroxy acid cul ~ ,u..di,~g to the bleach activator. Various nonlimiting examples of activators are disclosed in U.S. Patent 4,915,854, issued April 10, 1990 to Mao et al, and U.S. Patent 4,412,934. The jlu,~yben_ene sulfonate (NOBS) and tetraacetyl ethylene diamine (TAED) activators are typical, and mixtures thereof can also be used. See also U.S. 4,634,551 for other typical bleaches and activators useful herein.
Highly preferred amido-derived bleach activators are those of the formulae:
RIN(R5)C(O)R2C(O)L or RIC(O)N(R~)R2C(O)L
wherein Rl is an alkyl group containing from about 6 to about 12 carbon atoms, R2 is an alkylene containing from I to about 6 carbon atoms, R5 is H or alkyl, aryl, or alkaryl containing from about I to about 10 carbon atoms, and L is any suitable leaving group. A leaving group is any group that is displaced from the bleach ac-tivator as a c~ of the ll~ ' attack on the bleach activator by the p~ dlUI~ anion. A preferred leaving group is phenyl sulfonate.
Preferred examples of bleach activators of the above formulae include (6-o~ caproyl)u~b. ,..~ , (6-n.~
caproyl)u,.yl 'f~ ~, (6-.1~ -caproyl)u,~ , and 2s mixtures thereof as described in U.S. Patent 4,634,551.
Another class of bleach activators comprises the ben_oxa_in-type activators disclosed by Hodge et al in U.S. Patent 4,966,723, issued October 30, 1990. A
highly preferred activator ofthe b~n~.-Y~in type is:

~l"C~
Still another class of preferred bleach activators includes the acyl lactam activators, especially acyl ~ JIUI~ and acyl ~ ul~L.."I~ of the formulae:

WO 95119953 2 ~ 7 9 P~ 766 Il wherein R6 js H or an alkyl, aryl, alkoxyaryl, or alkaryl group containing from I to about 12 carbon atoms. Highly preferred lactam activators include benzoyl c~p.u14~ , octanoyl I~GIJlUlal..kllll, 3~5~5~ jlh~,Ao.lluyl ~ luld~;l2llll~ nonanoyl S ua~Jlul~ ll, decanoyl ,~ lG~ undecenoyl ~,.",.ul.~ .", benzoyl val~.ul~,~l~.., octanoyl v_' ula~ ", decanoyl v ' uk~ undecenoyl ~ ' ula.L~ nonanoyl V-l Ul~ lll, 3,5,5-l~ lh~Adlluyl val~luld~ and mixtures thereof. See also U.S. Patent 4,545,784, issued to Sanderson, October 8, 1985, which discloses acyl ula~ llla7 including benzoyl ~ ul~.,LOIll, adsorbed into sodium perborate.
Bleaching agents other than o~ ygen bleaching agents are also known in the art and can be utilized herein. One type of non-oxygen bleaching agent of particular interest includes photoactivated bleaching agents such as the sulfonated zinc and/or aluminum pl.ll.io~ . See U.S. Patent 47û337718, issued July 57 1977 to Holcombe et al. If used, detergent ~ will typically contain from about û.025% to about 1.25%, by weight, of such bleaches, especially sulfonate zinc (d) ~lilg~L - Detergent builders can optionally be included in the c.. ,~ l;,.. herein to assist in controlling mineral hardness. Inorganic as well as organic builders can be used. Builders are typically used in fabric laundering ~o c~ to assist in the removal of particulate soils.
The level of builder can vary widely depending upon the end use of the and its desired physical form. When present, the c.~ will typically comprise at least about 1% builder. Liquid r~ typically comprise from about 5% to about 50%, more typically about 5% to about 30%, by weight, of 2s detergent builder. Granular r...."..~-~;..,.~ typically comprise from about lû% to about 8û%7 more typically from about 15% to about 50% by weight7 of the detergent builder. Lower or higher levels of builder, however7 are not meant to be excluded.
Inorganic detergent builders include7 but are not limited to7 the alkali metal, ammonium and: " ' salts of IJOI~ Oa~ L~;a (~ r~ by the L.;~ , and glassy polymeric meta-phosphates), I' ,' , phytic acid, silicates, carbonates (including l".",.L and a~,~yu;~,~uL ' )~ sulphates, and: ' " However, non-phosphate builders are required in some locales. I~yul hu~lly~ the u~ ~ ,p~ , herein function ~UI~ well even in the presence of the so-called "weak" builders (as compared wo~ 99s3 ~17926~ T~1/O~ 16C ~

with phosphates) such as citrate, or in the so-called "underbuilt" situation that may occur with zeolite or layered silicate builders.
Examples of silicate builders are the alkali metal silicates, ~ ,ul~ly those having a SiO2:Na2O ratio in the range 1.6:1 to 3.2:1 and layered silicates, such as the layered sodium silicates described in U.S. Patent 4,664,839, issued May 12, 1987 to H. P. Rieck. NaSKS-6 is the trademark for a crystalline layered silicate marketed by Hoechst (commonly abbreviated herein as "SKS-6"). Unlike zeolite builders, the Na SKS-6 silicate builder does not contain aluminum. NaSKS-6 has the delta-Na2SiOs IIIUII ' I ,,y form of layered silicate. It can be prepared by methods such as those described in German DE-A-3,417,649 and DE-A-3,742,043. SKS-6 is a highly preferred layered silicate for use herein, but other such layered silicates, such as those having the general formula NaMSixO2x+l-yH2O wherein M is sodium or hydrogen, x is a number from 1.9 to 4, preferably 2, and y is a number from 0 to 20, preferably 0 can be used herein. Various other layered silicates from Hoechst include NaSKS-5, NaSKS-7 and NaSKS-I 1, as the alpha, beta and gamma forms. As noted above, the delta-Na2SiOs (NaSKS-6 form) is most preferred for use herein. Other silicates may also be usefiul such as for example magnesium silicate, which can serve as a crispening agent in granular r ""~ , as a stabilizing agent for oxygen bleaches, and as a component of suds control systems.
Examples of carbonate builders are the alkaline earth and alkali metal carbonates as disclosed in German Patent Application No. 2,321,001 published on November 15, 1973.
~1 ' builders are useful in the present invention. ~
builders are of great importance in most currently marketed heavy duty granular 25 detergent ,, ~ and can also be a significant builder ingredient in liquid detergent r~ Al " builders include those having the empirical formula:
MZ(zA102)y] XH20 wherein z and y are integers of at least 6, the molar ratio of z to y is in the range from 1.0 to about 0.5, and x is an integer from about 15 to about 264.
Useful :' ' ion exchange materials are commercially available.
These ' " can be crystalline or amorphous in structure and can be naturally-occurring _' ' or ~ ' '1~ derived. A method for producing ~ ' ' ion exchange materials is disclosed in U.S. Patent

3,985,669, Krummel, et al, issued October 12, 1976. Preferred synthetic crystalline ion exchange materials useful herein are available under the d- ;"! ~ "` Zeolite A, Zeolite P (B), Zeolite MAP and Zeolite X. In an especially ~ W0 95/199S3 2 ~ 7 9 2 6 7 r~ 766 preferred ~ l,o.l. ~ the crystalline ^' ~ ' ion exchange material has the formula:
Nal2[(A102)12(SiO2)12] xH2o - wherein x is from about 20 to about 30, especially about 27. This material is known S as Zeolite A Dehydrated zeolites (x = 0 - 10) may also be used herein. Preferably, the _' ' has a particle size of about 0.1-10 microns in diameter.
Organic detergent builders suitable for the purposes of the present invention include, but are not restricted to, a wide variety of pul~,a~bu~yldè ~ As used herein, "~ .albu~ laLe" refers to c~ u~ having a plurality of ~albu~laLe ~o groups, preferably at least 3 ua~bu~ylal~s POlyualllùr.yla~e builder can generally be added to the ~.,..l..,~l;.) in acid form, but can also be added in the form of aneutralized salt. When utilized in salt form, alkali metals, such as sodium, potassium, and lithium, or 2~ salts are preferred.
Included among the pOly~,a~u~yla~ builders are a variety of categories of useful materials. One important category of pûl~,al~u~.ylaLe builders ~
the ether pGl~,albuA~la~ea, including u~.y~i._ , as disclosed in Berg, U.S.
Patent 3,128,287, issued April 7, 1964, and Lamberti et al, U.S. Patent 3,635,830, issued January 18, 1972. See also "TMS/TDS" builders of U.S. Patent 4,663,071, issued to Bush et al, on May 5, 1987. Suitable ether ~,uly.,a.bu~lates also include 20 cyclic, . ', particularly alicyclic ~ .l u~ , such as those described in U.S. Patents 3,923,679; 3,835,163; 4,158,635; 4,120,874 and 4,102,903.
Other useful detergency builders include the ether I~Jdlu,~lJul~,allJw~ylaLca~
..ui.ol~ of maleic anhydride with ethylene or vinyl methyl ether, 1, 3, 5-trihydroxy benzene-2. 4. 6-~ ,l,.", acid, and C.àlbU~lll~,LllylU~yaUul~lluC acid, the 2~ various alkali metal, ammonium and substituted ammonium salts of polyacetic acids such as ~ tetraacetic acid and nitrilotriacetic acid, as well as pGl~.4~buA~' such as mellitic acid, succinic acid, u~yd;.,.~u.,;...~, acid, polymaleic acid, benzene 1~3~5-~ alluw~yl;~. acid, carbox~ lu~ya.,w,;,.ic acid, and solublesalts thereof.
Citrate builders, e.g., citric acid and soluble salts thereof (~al l;l,ulally sodium salt), are pul~,allJu~ylalé builders of particular importance for heavy duty liquid detergent r,...""~-:;.... due to their availability from renewable resources and their l,;o~ . Citrates can also be used in granular ~ ..., especially in .,u- l- -~;~- with aeolite andlor layered silicate builders. O~y~ - ~. .: A: - are also 3s especially useful in such ~;.. l.,~:l,,.. c and ~.. ,.l.: -~;.. ~
Also suitable in the detergent ~ of the present invention are the 3,3-dicarboxy4-oxa-1,6 l - ~ and the related U ,.I u ~ disclosed in U.S.

Wo gS/199~3 ~ 66 21~9267 ~

Patent 4,566,984, Bush, issued January 28, 1986. Useful succinic acid builders include the Cs-C20 alkyl and alkenyl succinic acids and salts thereof. A particularly preferred compound of this type is dodecenylsuccinic acid. Specific examples of succinate builders include: I~U~ CC;~ uc~ la~c, I ' yl~u~ .a~c, 2-s dodc~ (preferred), 2-pentadccc~ l,uc.,;..~.~e, and the like.
h~u~yl;..lu~,;lldtcs are the preferred builders of this group, and are described in European Patent Application 86200690.5/0,200,263, published November 5, 1986.
Other suitable ~ul.yc~ u~ylc~es are disclosed in U.S. Patent 4,144,226, Crutch'deld et al, issued March 13, 1979 and in U.S. Patent 3,308,067, Diehl, issued March 7, 1967. See also Diehl U.S. Patent 3,723,322.
Fatty acids, e.g, C12-CIg ~u~lour~llJu~yl;~ acids, can also be i..~,u.~,u,d~el into the ~ alûne, or in ~O-I~ with the aforesaid builders, especially citrate and/or the succinate builders, to provide additional builder activity. Such use of fatty acids will generally result in a diminution of sudsing, which should be take~
5 into account by the formulator.
In situations where pl~u~ ulus-based builders can be used, and especially in the ~ ;.... of bars used for hand-laundering operations, the various alkali metal phosphates such as the well-known sodium l~ lyl ~ . sodium ~ 1 1 U~ 3~Jl.dt~
and sodium ù.i' rl ,' can be used. p~ t~ builders such as ethane-l-20 hydroxy-l,l-.l:l l ~ and other known l,l ~ J ,~ (see, for example, U.S.
Patents 3,1597581 3,213,030 3,4æ,021; 3,400,148 and 3,422,137) can also be used.
(e) Pol~meric Soil Release Agent - Any polymeric soil release agent known to those skilled in the art can optionally be employed in the .~ and 25 processes ofthis invention. Polymeric soil release agents are c;l~llacLc~;~cd by having both hydrophilic segments, to l~ydll I ' ' the surface of ~J~u~ ùbic fibers, such as polyester and nylon, and }~JJ~u~ ub;c segments, to deposit upon l~ u~llubic fibers and remain adhered thereto through completion of washjng and rinsing cycles and,thus, serve as an anchor for the hydrophilic segments. This can enable stains 30 occurring subsequent to treatment with the soil release agent to be more easily cleaned in later washing procedures.
The polymeric soil release agents useful herein especially include those soil release agents having: (a) one or more nonionic hydrophile ..~ consisting essentially of (i) polyu~ ylene segments with a degree of polymerization of at least5 2, or (ii) U~l)IU~JJI~ or pc,lyu,.y~,.u~,yL,.lc segments with a degree ofdLiu~ of from 2 to 10, wherein said hydrophile segment does not encompass any u~nu~!u.~c unit uniess it is bonded to adjacent moieties at each end by ether ~ wo 95/19953 ~? 1 7 9 2 6 7 ~ /66 linkages, or (iii) a mixture of oxyalicylene units comprising oxyethylene and from I to about 30 u~yl~-u~ units wherein said mixture contains a sufficient amount of u~ units such that the hydrophile component has ll/Jl.r' ' ~y great - enough to increase the }Iy ilU~lil;l;~;~y of ,u.. ~.-L;oll~l polyester synthetic fiber s surfaces upon deposit of the soil release agent on such surface, said hydrophile segments preferably comprising at least about 25% u~ lc.~e units and more preferably, especially for such ~ having about 20 to 30 u~y~lu~;h,.l., units, at least about 50% u7~ le units; or (b) one or more lly ilu~ obe CfJ~ O~
comprising (i) C3 u~ " ~ elt~ llGldt~, segments, wherein, if said II~ilUIJIIUiJ~, 10 ~ also comprise u~.,ll~ tl t~lllllGlG~e, the ratio of oxyethylene ItlclJlllllGlGle.C3 u~di~!c.~ tltl)llllldlG~e units is about 21 or lower, (ii) C4-C6 alkylene or oxy C4-C6 alicylene segments, or mixtures therein, (iii) poly (vinyl ester) segments, preferably poly9vinyl acetate), having a degree of pOlylll~ GI;ull of at least 2, or (iv) Cl-C4 alkyl ether or C4 I~y i.u~ycli~yl ether ~ or mixtures 5 therein, wherein said, ~ are present in the form of C l-C4 aikyl ether or C4 hy~ilu~Gli~yl ether cellulose deriYatives, or mixtures therein, and such cellulose derivatives are ~ ''', whereby they have a sufficient level of Cl-C4 alkyl etherand/or C4 II~ilU~dli~yl ether units to deposit upon CUII.~ ;f~I~GI polyester synthetic fiber surfaces and retain a sufficient level of hydroxyls, once adhered to such 2J CU~ II;OI)GI synthetic fiber surface, to increase fiber surface l~ u~lfd;~,;ly, or a ;. of (a) and (b) Typically, the polyu~ /L,..e segments of (a)(i) will have a degree of pU~ Gl;Ull of from about 200, although higher levels can be used, preferably from 3 to about 150, more preferably from 6 to about 100 Suitable oxy C4-C6 25 aikylene ~ segments include, but are not limited to, end-caps of polymeric soii release agents such as MO3S(CH2)nOCH2CH2O-, where M is sodium and n is an integer from 4-6, as disclosed in U S Patent 4,721,580, issued January 26, 1988 to Gosselinic Polymeric soil release agents usefiul in the present invention also include 30 cellulosic derivatives such as lly i~u~ cellulosic polymers, cu~olyll..,.;~, blocks of ethylene IcleLJilil~GlG~e or propylene Itlc,ull~llGlG~e with polyethylene oxide or ~f~ -u~JJL,.-., oxide lelclJllLlldlG~c~ and the like Such agents are CUIIIIII~e;GII) available and include h/Jlu~,.h~ of cellulose such as METHOCEL (Dow) Cellulosic soil release agents for use herein also include those selected from the 3s group consisting of Cl-C4 alkyl and C4 hydroxyalkyl cellulose; see U S Patent 4,000,093, issued December 28, 1976 to Nicol, et al Soil release agents ~IlGlGl,Lcll~_J by poly(vinyl ester) I~/J~u~l.ui~, segments wo 95119953 ~ I .111J..,5~'~ 166 ~
~ 92~7 16 include graft copolymers,of poly(vinyl ester), e.g., Cl-C6 vinyl esters, preferably poly(vinyl acetate) grafted onto polyalkylene oxide backbones, such as pGI~ ylelle oxide backbones. See European Patent Application 0 219 048, published April 22, 1987 by Kud, et al. Cu~ V available soil release agents of this kind include s the SOKALAN type of material, e.g., SOKALAN HP-22, available from BASF
(West Germany).
One type of preferred soil release agent is a copolymer having random blocks of ethylene lc.~, ' ' ' and pol~Lh,!~,.. oxide (PEO) telq~ . The molecular weight of this polymeric soil release agent is in the range of from about 25,000 to about 55,00û. See U.S. Patent 3,959,230 to Hays, issued May 25, 1976 and U.S.
Patent 3,g93,929 to Basadur issued July 8, 1975.
Another preferred polymeric soil release agent is a polyester with repeat units of ethylene l~,c~ L.~ units containins 10-15% by weight of ethylene Lclc~JllLll,lhll~
units together with 90-80% by weight of polyu~.,.l-ylene terephthalate units7 derived from a pGI~v,~ c glycol of average molecular weight 300-5,000. Examples of this polymer include the Culllm~ available material ZELCON 5126 (from Dupont) and MILEASE T (from ICI). See also U.S. Patent 4,702,8~7, issued October 27, 1987 to Gosselink.
Another preferred polymeric soil release agent is a sulfonated product of a 20 ' s' ''~1 linear ester oligomer comprised of an oligomeric ester backbone of ltlelJl.il~.~lvyl and u~ "yh,..~ y repeat units and terminal moieties covalentlyattached to the backbone. These soil release agents are described fully in U.S. Patent

4,968,451, issued November 6, 1990 to J.J. Scheibel and E.P. Gosselink. Other suitable polymeric soil release agents include the ~elc~Jhllldl~Le polyesters of U.S.
2s Patent 4,711,730, issued December 8, 1987 to Gosselink et al, the anionic end-capped oligomeric esters of U.S. Patent 4,721,580, issued January 26, 1988 to Gosselink, and the block pûlyester oligomeric r.",.l,v~ of U.S. Patent 4,702,857, issued October 27, 1987 to Gosselink.
Preferred polymeric soil release agents also include the soil release agents of U.S. Patent 4,877,896, issued October 31, 1989 to Maldonado et al, which discloses anionic, especially sulfoarolyl, end-capped tele~ e esters.
If utilized, soil release agents will generally comprise from about 0.01% to about 10.0%, by weight, of the detergent, ~ herein, typically from about 0.1% to about 5%, preferably from about 0.2% to about 3.0%.
3s (f) ~'~ ' A~ents - The detergent ~"",l.v~ herein may also optionally contain one or more iron and/or manganese chelating agents. Such chelating agents can be selected from the group consisting of amino c~l~lJu~ylo.ie~, ~ WO 95/19953 ~ 1 7 9 2 6 ~ r~ 166 :~
amino l,l,~,~l,l,,,..-l~ " polyfunctionally-substituted aromatic chelating agents and mixtures therein, all as hereinafter defined. Without intendine to be bound by theory, it is believed that the benefit of these materials is due in part to their exceptional ability to remove iron and manganese ions from washing solutions by formation ofs soluble chelates.
Amino ua~l~uA.~l~t~ useful as optional chelating agents include ethylenedia-" ,.~e~l~ce~ .., N ~J~U~ LI~ t~ ~, II;I-;IULI;~ ,L4L~, ethyl-enediamine Le~laill. , L~ Ll-yl - Irl.A~..,.,.h A P1Al.~ d;~Lll~ ,;""""
p ~ ~P~ and eLi._.~oldi~,;...,." alkali metal, ~rnmr~ni~lrn, and substituted am-10 monium salts therein and mixtures therein.
Amino pl . ' are also suitable for use as chelating agents in the~c~ of the invention when at lease low levels of total l' ,' us are permitted in detergent cnnnrr~Citir~nc~ and include eLl~ aki~
- ~1 rl)l,"~ ) as DEQUEST. Preferred, these amino l l r~L,I,.. -:~ to, 15 not contain alkyl or alkenyl groups with more than about 6 carbon atoms.
rvly," "~ substituted aromatic chelating agents are also usefiul in the herein. See U.S. Patent 3,812,û44, issued May 21, 1974, to Connor et al. Preferred ~ u ..1~ of this type in acid form are dihydroxy~l:~,.ll..l,. .. ~ such as 1,2-dihydroxy 3,5 ,1~ lr~
A preferred ;;od.,~ d,~l~ chelator for use herein is ~
disuccinate ("EDDS"), especially the [S,S] isomer as described in U.S. Patent 4,7û4,233, November 3, 1987, to Hartman and Perkins.
If utilized, these chelating agents will generally comprise from about 0.1% to about lû% by weight of the detergent , herein. More preferably, if 2s utilized, the chelating agents will comprise from about 0.1% to about 3.0% by weight of such ~ l u~
(g) Clay Soil RemovaU~nti-,,d~,vr.~ .. A~n~c - The r.,, ~ of the present invention can also optionally contain water-soluble ethoxylated amines having clay soil removal and All~ properties. Granular detergent ~ u~ which contain these c~ u~ typically contain firom about 0.01% to about 10.0% by weight of the water-soluble ethoxylates amines; liquid detergent - c~ l.r~ typically contain about 0.01% to about ~i%.
The most preferred soil release and anti-lrd~ agent is ethoxylated LeLI .,.~ Exemplary ~Ll.u,.~,.ALed amines are further described in U.S.
Patent 4,597,898, VonriPrMPPr~ issued July 1, 1986. Another group of preferred clay soil removal-,~.L;l~ v~ agents are the cationic i ,l.v l~ disclosed in European Patent Application 1 11,965, Oh and Gosselink, published June 27, 1984.

woss/l9953 ~ 7~ '-f' 18 ~,,.~,. . /66 Other clay soil l~lllUV '/.:llI~ilt''l' l'V` I;II'~ agents which can be used include the ~I,u~yla~d amine polyrners disclosed in European Patent Application 111,9841 Gosslink, published June 2~, 1984; the ~wi~liulfJc polymers disclosed in European Patent Application 112,592, Gosselink, published July 4, 1984; and the amine oxides disclosed in U.S. Patent 4,548,744, Connor, issued October 22, 1985. Other clay soil removal and/or anti . ~ ;. agents known in the art can also be utilized in the ~ , herein. Another type of preferred ~ - - agent includes the carboxy methyl cellulose (CMC) materials. These materials are well known in the art.
(h) Polvmeric Dispersin~ A~ents - Polymeric dispersing agents can ad~ ..6~,uual.~ be utilized at levels from about 0.1% to about 7%, by weight, in the ,... I...~.l;.~.~c herein, especially in the presence of zeolite andlor layered silicate builders. Suitable polymeric dispersing agents include polymeric pol,y~ bù;~.ylcl~,S
and pol~ h,l~, glycols, although others known in the art can also be used. It is5 believed, though it is not intended to be limited by theory, that polymeric dispersing agents enhance overall detergent builder p.,.fUllll~ ,t, when used in ~
with other builders (including lower molecular weight polyl,~bu~ldlca) by crustal growth inhibition, particulate soil release p~rti7~1tir~n and anti-,~
Polymeric pulr.,~bu~yL~ materials can be prepared by p~ or 20 ~,UI:Iul~ 7 suitable Llllaa~uldLt~ monomers, preferably in their acid form.
Unsaturated monomeric acids that can be pGI,ylll~,,i~.l to forrn suitable polymeric puly~,~bu~h ~I l include acrylic acid, maleic acid (or maleic anhydride), fumaric acid, itaconic acid, aconitic acid, mesaconic acid, citraconic acid and .,.. ,.IIjl.. ,.. I~,.. :~
acid. The presence in the polymeric poly~..l,u,.yla~ts herein or monomeric segments, 25 containing no carboxylate radicals such as finylmethyl ether, styrene, ethylene, etc. is suitable provided that such segments do not constitute more than about 40% by weight.
Particularly suitable polymeric poly.,~ u,.~' can be derived from acrylic acid. Such acrylic acid-based polyrners which are useful herein are the water-soluble 30 salts of p~ i~d acrylic acid. The average molecular weight of such polymers in the acid form preferably ranges from about 2,000 to 10,000, more preferably fromabout 4,000 to 7,000 and most preferably from about 4,000 to 5,000. Water-soluble salts of such acrylic acid polymers can include, for example, the alkali metal, ammonium and substituted ammonium salts. Soluble polymers of this type are 35 known materials. Use of pblf~ L.t~,i of this type in detergent c.,,..l..,~ has been disclosed, for example, in Diehl, U.S. Patent 3,308,067, issued march ~, 1967.
A~ liJ ' -based cOpul~ .a may also be used as a preferred component ~ WO95/19953 21~9267 r~l~u.. ~.~ 766 of the d;.~ agent. Such materials include the water-soluble -salts of uopc~ of acrylic acid and maleic acid. The average molecular weight ofsuch l,U~10l,~ in the acid form preferably ranges from about 2,000 to 100,000, more preferably firom about 5,000 to 75,000, most preferably from about 7,000 tos 65,000. The ratio of acrylate to maleate segments in such l,UpO~ will generally rangefromabout30:1toaboutl:1,morepreferablyfiromaboutlO:lto2:1. Water-soluble salts of such acrylic acidlmaleic acid copolymers can include, for example, the alkali metal, ammonium and substituted ammonium salts. Soluble ~ t~' ' ~UI)VI~/..l...:~ ofthis type are known materials which are described in European Patent Application No. 66915, published December 15, 1982.
Another polymeric material which can be included is polyethylene glycol (PEG). PEG can exhibit dispersing agent y..r as well as act as a clay soil removal-all~ agent. Typical molecular weight ranges for these purposes range from about 500 to about 100,000, preferably from about 1,000 to about 50,000, more preferably from about 1,500 to about 10,000.
rUl.~aa~Jall~e and pOly~lu~ aLe dispersing agents may also be used, especially in ~ - with zeolite builders. Dispersing agents such as pGI.ya~"al l~l~ preferably have a molecular weight (avg.) of about 10,000.
(i) Bri~htener - Any optical brighteners or other brightening or whitening 20 agents known in the art can be ;".u~yul~Ltd at levels typically from about 0.05/O to about 1.2%, by weight, into the detergent ~ herein. Commercial optical brighteners which may be use&l in the present invention can be classified into subgroups, which include, but are not necessarily limited to, derivatives of stilbene, pyrazoline, coumarin, carboxylic acid, Ill~ a~ .Gb~ ulll~ S~S-dioxide~
2s azoles, 5- and 6-membered-ring ll.,u~,y~.lu~, and other l~ agents.
Examples of such brighteners are disclosed in "The Production and Application ofFluorescent ~ u Agents", M. Zahradnik, Published by John Wiley & Sons, New York (1982).
Specific examples of optical brighteners which are use&l in the present 4~ are those identified in U.S. Patent 4,790,856, issued to Wixon on December 13, 1988. These brighteners include the PHORWHITE series of brighteners from Verona. Other brighteners disclosed in this reference include:
Tinopal ~NPA, Tinopal CBS and Tinopal 5BM; available from Ciba-Geigy; Artic White CC and Artic White CWD, available from Hilton-Davis, located in Italy; the 2-3s (4-stryl-phenyl)-2H-napthol[1,2-d]triazoles; 4,4'-bis- (1,2,3-triazol-2-yl)-stil- benes;
4,4'-bis(stryl)bisphenyls; and the ~ u~ Specific examples of these brighteners include 4-methyl-7-diethyl- amino coumarin; 1,2-bis(....,: .,.lA~.11_2_ wo ss~lsss3 ~ ; . P~ 66 ~
~17~267 20 yl)ethylene; 1,3-diphenyl-p~,l " , 2,5-bis(benzoxazol-2-yl)thiophene; 2-stryl-napth-[1,2-d]oxazole; and 2-(~ 1 yl)-2H-naphtho- [1,2-d]triazole See also U S. Patent 3,646,015, issued February 29, 1972 to Hamilton. Anionic brightenersare preferred herein.
s (j) Suds Suprressors - (~nrnro~ln~c for reducing or Su,ulncaa;llg the formation of suds can be ;l~,ul~-ul~Lcd into the f ~ of the present invention.
Suds au~ l caa;ù~l can be of particular A wide variety of materials may be used as suds suppresors, and suds ~u~,i,,~,u,, are well known to those skilled in the art. See, for example, Kirk Othmer E~IUJ~IUIJ~J;~ of Chemical Technology, Third Edition, Yolume 7, pages 430-447 (John Wiley & Sons, Inc., 1979). One category of suds suppressor of particular interest ~ IIIVIIOUaIbU~ fatty acids and soluble salts therein. See U.S.
Patent 2,954,347, issued September 27, 1960 to Wayne St. John. The uual~u~.yli_ fatty acids and salts thereof used as suds suppressor typically havç
~l~Jlu~albyl chains of 10 to about 24 carbon atoms, preferably 12 to 18 carbon atoms. Suitable salts include the alkali metal salts such as sodium, potassium, and lithium salts, and ammonium and 5~ - salts.
The detergent .. ~.l.v~ l,.,.. ~ herein may also contain non-surfactant suds au~ ula. These include, for example: high molecular weight Il~JluuallJull~ such 20 as parafiin, fatty acid esters (e.g., fatty acid L~ ,cli~), fatty acid esters of Il~ulluv~ ,lt alcohols, aliphatic C18-C40 ketones (e.g., stearone), etc. Other suds inhibitors include N-alkylated amino triazines such as tri- to hexa-alk~' ' or di- to tetr~ ulllùl Ll;~;.l~,~ formed as products of cyanuric chloride with two or three moles of a primary or secondary amine containing I to 24 carbon atoms, 2s propylene oxide, and yl phosphates such as monostearyl alcohol phosphate ester and IllulluaL.,~ I di-alkali metal (e.g., K, Na, and Li) phosphates and phosphate esters. The h~JIU~U~ such as paraftin and I ' r ~ can be utilized in liquid form. The liquid hJIluualbulla will be liquid at room i , c and ~lllua~Jh_.;c pressure, and will have a pour point in the range of about -40C and about 5ûC, and 30 a minimum boiling point not less than about 11 0C (~I~lllua~Jh~ . pressure). It is also known to utilize waxy lly.lluua.lJulla, preferably having a melting point below about 10ûC. The ll~dlul,~lbulla constitute a preferred category of suds suppressor for detergent ~ IIydlu~lbùl~ suds au~J~ncaaula are described, for example, in U.S. Patent 4,265,779, issued May 5, 1981 to Gandolfo et al. The ~.lluu~lb~lla, 3s thus, include aliphatic, alicyclic, aromatic, and heterocyclic saturated or .... ~
Il~J~uua~bu.~s having from about 12 to about 70 carbon atoms. The term "paraffin,"
as used in this suds suppressor discussion, is intended to include mixtures of true - - - = ~ -~ WO 95/19953 2 1 7 ~ 2 6 7 ~ o6 paraffims and cyclic h~d~u~,G~iJui~s.
- Another preferred category of non-surfactant suds SUyylc~aula comprises silicone suds auy~ )la. This category includes the use of p~i.yUl~,AIl. 1-'~'1. A.l~ oils such as poly," ~la;luAGl~e, dispersions or emulsions of pGlJvl~ oils or s resins, and c~ ;- of POI~UI~ A P with silica particles wherein the polyu,~,----.- ~ - is ~,h~.l..~uli,.,d or fiused onto the silica. Silicone suds auyy~c~u1S are well icnown in the art and are, for example, disclosed in U.S. Patent 4,265,779, issued May 5, 1981 to Gandolfo et al and European Patent Application No. 893û7851.9, published February 7, 1990, by Starch, M. S.
Other silicone suds au~ylcaaula are disclosed in U.S. Patent 3,455,839 which relates to ~ and processes for defoaming aqueous solutions by i...,olyul~ therein small amounts of pOly i;l-l~,Ll~jla;lu~ , fluids.
Mixtures of silicone and silanated silica are described, for instance, in GermanPatent Application DOS 2,124,526. Silicone defoamers and suds controlling agent,s 15 in granular detergent ~.. 1.~ ~ l;.. ~ are disclosed in U.S. Patent 3,933,672, Bartolotta et ai, and in U.S. Patent 4,652,392, Baginsici et ai, issued March 24, 1987.
An exemplary silicone based suds suppressor for use herein is a suds yl~a;ll~ amount of a suds controlling agent consisting essentially of (i) i~Ul~ hyl~;lu~ lc fluid haYing a ~iscosity of from about 20 cs. to A~O about 1,500 cs. at 25C;
(ii) from about 5 to about 50 parts per 100 parts by weight of (i) of siloxane resin composed of (CH3)3SiOI/2 units of SiO2 units in a ratio of from (CH3)3 SiOl/2 units and to SiO2 units of from about 0.6:1 to about 1.2:1, and A~S (iii) from about I to about 20 parts per 100 parts by weight of (i) of a solid silica gel.
In the preferred silicone suds suppressor used herein, the solvent for a continuous phase is made up of certain pol.~.,Lh~ c glycols or pGI~.,~l.fl~",C-pGl~yluyJL"~ glycol .,ul.ul~....,.~ or mixtures thereof (preferred). and not 30 pol~ u~ ,.lc glycol. The primary silicone suds suppressor is b~G~,h~d/~"u~ cd and not linear.
To illustrate this point further, typical liquid laundry detergent ...,,,,1,,,~;l;., ~
with controlled suds will optionally comprise from about 0.001 to about 1, preferably from about û.01 to about 0.7, most preferably from about û.ûS to about 0.5, weight 35 % of said silicone suds suppressor, which comprises (1) a ~ emulsion of a primary antifoam agent which is a mixture of (a) a PCII~YUI~ , (b) a resinous siloxane or a silicone resin-producing silicone compound, (c) a finely divided filler wo 951199~3 2 1 7 9 2 6 ~ r~ C.a /66 ~

, .
material, and (d) a catalyst to promote the reaction oF mixture ~.,. ~.., .,l~ (a), (b) and (e), to form silanolates; (2) at least one nonionie silicone surfactant; and (3) p~ , glycol or a copolymer of polyethylene-p~ ,.ul.~l...e glycol having a solubility in water at room L~ ,.dLul ~ of more than about 2 weight %, and without s pol~"u~JL...e glycol. Similar amounts can be used in granular ~ . gels, ete. See also U.S. Patents 4,978,471, Starch, issued Deeember 18, 1990, and 4,983,316, Stareh, issued January 8, 1991, and U.S. Patents 4,639,489 and 4,749,740, Aizawa et al at eolumn 1, line 46 through eolumn 4, line 35.
The silieone suds suppressor herein preferably comprises P~ J~LIIJI~IC glyeol 0 and a eopolymer of pol~.,.l,1h,..c glycoi/pul~lu~ glycol, all having an average molecular weight of less than about 1,000, preferably between about 100 and 800.The pol~ c glycol and pol~....Jl~.lc/poly~.lu~ copolymers herein have a solubility in water al room L~ ,.dLul~: of more than about 2 weight /0, preferably more than about 5 weight %.
The preferred solvent herein is polyethylene glyeol having an average moleeular weight of less than about l,00û, more preferably between about 100 and800, most preferably between 200 and 400, and a eopolymer of polyethylene glyeoi/pu:1~Jlu~ glycol, preferably PPG 200/PEG 300. Preferred is a weight ratio of between about 1:1 and 1:10, most preferably between 1:3 and 1:6, of 20 p~ Lhtlucglycol:eopolymerofpolyethylene-pol;plu~ glyeol.
The preferred silieone suds au~ lcaaul~ used herein do not eontain pul~ uuylu..~, glyeol, partieularly of 4,000 moleeular weight. They also preferably do not eontain bloek copolymers of ethylene oxide and propylene oxide, like PLURONIC L101 .
2s Other suds au~u~ull,~avl~ useful herein comprise the secondary alcohols (e.g., 2-alkyl alkanols) and mixtures of such alcohols with silicone oils, such as the silicones disclosed in U.S. 4,798,679, 4,075,118 and EP 150,872. The secondary alcohols inelude the C6-C16 aikyl alcohols having a Cl-C16 chain. A preferred alcohol is 2-butyl oetanol, whieh is available from Condea under the trademark ISOFOL 12.
Mixtures of seeondary alcohols are available under the trademark ISALCi lEM 123 from Enichem. Mixed suds au~ aula typically comprise mixtures of alcohol +
SiiiCone at a weight ratio of 1:5 to 5:1.
For any detergent . , to be used in automatic laundry washing machines, suds should not form to the extent that they overtiow the washing maehine. Suds au~ aaUI a, when utilized, are preferably present in a "suds su~ amount. By "suds au~ g amount" is meant that the formulator of the ~ ean seieet an amount of this suds controlling agent that will WO 9S119953 ~ P~ . . /66 sufficiently control the suds to result in a low-sudsing laundry detergent for use in automatic laundry washing machines The r~ herein will generally comprise from 0% to about 5% of suds suppressor When utilized as suds ~u~ c~v~ ollo.,~.L,u~ylic fatty acids, ands salts therein, will be present typically in amounts up to about 5%, by weight, of the detergent ~ u~ Preferably, from about 0.5% to about 3% of fatty l,uA~l~Le suds suppressor is utilized. Silicone suds ~u~ t~aul~ are typically utilized in amounts up to about 2.0%, by weight, of the detergent . .,ci~ io,i, although higher amounts may be used. This upper limit is practical in nature, due 0 primarily to concern with keeping costs minimized and c~ of lower amounts for effectively controlling sudsing. Preferably from about 0.01% to about 1% of silicone suds suppressor is used, more preferably from about 0.25% to about 0.5%. As used herein, these weight percentage values include any silica that may be utilized in ~u ~ with p~l~ul~ , as well as any adjunct materials tha,t

5 may be utilized. Moll~J~t~,alyl phosphate suds ~u~ are generally utilized in amounts ranging from about 0.1% to about 2%, by weight, of the ~.u..~
Hydlu~/llbull suds su~ ul~ are typically utilized in amounts ranging firom about0.01% to about 5.0%, although higher levels can be used. The alcohol suds ~U~ Ul~ are typically used at 0.2%-3% by weight ofthe finished ~.u..~l.o~;l;u ~
(k) Fabric Softeners - Various through-the-wash fabric softeners, especially the impalpable smectite clays of U.S. Patent 4,062,647, Storm and Nirschl, issued December 13, 1977, as well as other soRener clays known in the art, can optionally be used typically at levels of firom about 0.5% to about 10% by weight in the present ~ J`;I;~ ` to provide fabric softener benefits ~ Lly with fabric 2s cleaning. Clay softeners can be used in c.~ l; -';.~, with amine and cationic softeners as disclosed, for example, in U.S Patent 4,375,416, Crisp et al, March 1, 19g3 and U.S. Patent 4,291,071, Harris et al, issued September 22, 1981.
(I) Detersive Surfactants - ~ ' _ examples of surfactants useful herein typically at levels from about 1% to about 55%, by weight, include the .,oll~ ;c.nal Cl I-C 18 alkyl benzene sulfonates ("LAS") and primary, branched-chain and random Clo-C20 alkyl sulfates ("AS"), the Clo-CIg secondary (2,3) alkyl sulfates of the formula CH3(CH2)X(CHOSO3 M ) CH3 and CH3 (CH2)y(CHOSO3 M ) CH2CH3 where x and (y + 1) are integers of at least about 7, preferably at least about 9, and M is a water- ' ' ' ,, cation, especially sodium, 3s ~ sulfates such as oleyl sulfate, the Clû-Clg alkyl alkoxy sulfates ("AEXS"; especially EO 1-7 ethoxy sulfates), Clo-CIg alkyl alkoxy l,~bu~l~,~
(especially the EO 1-5 ethoxy~ u~ e~), the C 10-18 glycerol ethers, the C lo-C 18 WO 95/19953 ~ ,. 766 ~
~17~2~7 alkyl pu1~ - os;d~,~ and their ~ulle~)ullJ;Ilg sulfated pûly~ .u~ , and C12-C18 alpha-sulfonated falty acid esters. If desired, the Cu,.~ Liu~l nonionic and amphoteric surfactants such as the C12-CIg alkyl ethoxylates ("AE") including the so-called narrow peaked alkyl ethoxylates and C6-C12 alkyl phenol alkoxylates S (especially ethoxylates and mixed e~llu~yl~lulJuf~), C12-CIg betaines and ~ "` ' ("sultaines"), CIU CI8 amine oxides, and the like, can also be included in the overall ~ u ~ The C lo-C I g N-alkyl pùl~ dl w~y fatty acid amides can also be used. Typical examples include the C12-CIg N-methyl~ See WO
9,206,154. The N-propyl through N-hexyl C 1 2-C 18 glucamides can be used for low o sudsing. Clo-C20 ~,ul~ ;ull~l soaps may also be used. If high sudsing is desired, the branched-chain Clo-C16 soaps may be used. Mixtures of anionic and nonionic surfactants are especially useful. Other conventional useful surfactants are listed in standard texts.
The present invention ~, ,,, ,1,~ ~ l ,, ,, ,~ may also comprise oleoyl sarcosinate, in 15 its acid and/or salt form selected as desired for the ~ and uses herein, having the following formula:
o wherein M is hydrogen or a cationic moiety. Preferred M are hydrogen and alkali metal salts, especially sodium and potassium. Oleoyl sarcosinate is ~,UIIUII~,.'' "y available, for example as Hamposyl O supplied by W. R. Grace & Co. C..., ~
according to the present invention can typically comprise from about 0.1% to about 5~%, preferably from about 1% to about 20%, and most preferably from about 3% toabout 15%, of oleoyl sarcosinate by weight of the ~
In addition to the l,UIIIII~ available oleoyl :~al~ , oleoyl sarcosinate useful herein can also preferably be prepared from the ester (preferably the methyl ester) of ûleic acid and a sarcosine salt (preferably the sodium salt) under anhydrous reaction conditions in the presence of a base catalyst with a basicity equal to or greater than alkoxide catalyst (preferably sodium methoxide). For example, the reaction may be illustrated by the scheme:

2 7g267 wo ss/lsss3 ~ r~l~u~ 66 O

+

H,NJ~ONa NaOCH3 (cat) This salt may optionaily be neutralized to fomm the oleoyl sarcosinate in its acid fomm.
The preferred method for preparing oleoyl sarcosinate is conducted at a ~c~ a~ul~ from about 80C to about 200C, especially from about 120C to about 200C. It is preferred to conduct the reaction without solvent although alcohol solvents which have a boiling point of at least 100C and are stable to the reaction conditions (ie. giycerol is not acceptable) can be used. The reaction may proceed in about 85% yield with a molar ratio of methyl ester reactant to sarcosine salt reactant to basic catalyst of about 1:1:0.05-0.2.
Methyl ester mixtures derived from high oleic content natural oils (preferably having at least about 60%, more preferably at least about 75%, and most preferably at least about 90% oleic content) are especially preferred as starting materials.
Examples include high-oleic sunfiower and rapeseed/canola oil. In addition, a high-S oleic methyl ester fraction derived from either palm kemel oil or tallow is acceptable.
It is to be u~P~st~od that such oils typically will contain some levels of impurities, including some fatty acid impurities that may be converted to sarcosinate ç~mrolm~c by this synthesis method. For example, commodity canola/rapeseed oil may comprise a majority of oleic acid, and a mixture of fatty acid impurities such as palmitic, 20 stearic, iinoleic, linolenic and/or eicosenoic acid, some or all of which are converted to the sarcosinate by this reaction method. If desired for r ~ '- purposes, someor aii of such impurity materials may be excluded from the $arting oil before preparing the oleoyl sarcosinate to be used in the present ~ o~

WO95/19953 - F~ U., C'~ /66 ~'~7g267 Finally, sarcosine remaining in the reaction mixture can be converted to an amide by addition of maleic or acetic anhydride to the mixture, thereby minimizing the sarcosine content and any potential for formation of undesired nitrogen-containing impurities.
s The synthesis of oleoyl sarcosinate may be carried out as follows to prepare the sodium oleoyl af.~l Synthesis of Oleoyl Amide of Sarfn~inf- So~ -nn Salt - A 2 L, 3-neck, round bottom flask is fitted with ll... "l.~.... l.." Dean-Stark trap with condenser, mechanical stirring, and a gas inlet adapter through which nitrogen is passed over the reaction lo mixture. The reaction vessel is charged with sarcosine (43.3 g, 0.476 mol), sodium methoxide 25% in methanol (97.7 g, 0.452 mol), and methanol (400 mL). The reaction is refluxed 15 min to neutralize the sarcosine and then methyl ester derived from Cargill regular high-oleyl sunflower oil (148.25 g, 0.5 mol) is added. After the methanol is removed with the Dean-Stark trap, reaction mixture is heated to 170C
for I hr to drive off any water. The reaction is initiated by the addition of sodium methoxide 25% in methanol (15.4 g, 0.0714 mol). Reaction is kept at 170C for 2.5 hr during which methanol is collected in the Dean-Stark trap The reaction is allowed to cool slightly and then methanol (200 g) is added. Maleic anhydride (9.43 g, 0.095 mol) is added to the methanol solution and the reaction is stirred at 60C for 0.5 hr. Then most ofthe methanol is removed by rotary C~S~ nal;ull and acetone (2 L) is added to precipitate the product. The product is collected by suction filtration and allowed to air dry to give an off-white solid. Analysis of the reaction mixture by GC indicates the majority of the product is oleoyl sarcosinate, with minor amounts of the following impurities: sarcosine, oleic acid, and the af." derived from palmitic acid, stearic acid, and linoleic acid.
(m) Dye Transfer Inhibitinv A~ents - The ~ of the present invention can also optionally include one or more materials effective for inhibiting the transfer of dyes from one fabric to another during the cleaning process. Generally, such dye transfer inhibiting agents include polyvinyl IJy-l~ ' ' polymers, polyamine N-oxide polymers, copolymers of N-~;..yl~ and N ~
~ u~d~a~a, and mixtures thereof. If used, these agents typically comprise from about 0.01% to about 10% by weight of the Cf""l"J` I "". preferably from about 0.01% to about 5%, and more preferably from about O.OS% to about 2%.
3s More specifically, the polyamine N-oxide polymers preferred for use herein contain units having the following structura~ formula: R-AX-P; wherein P is a p~ blf unit to which an N-O group can be attached or the N-O group can wo 95119953 ~17 ~ 2 6 7 r~l~u~ /66 form part of the pOIyll.."i,al,l~ unit or the N-O group can be attached to both units;
A is one of the following structures: -NC(O)-, -C(O)O-, -S-, -O-, -N=; x is 0 or 1;
and R is aliphatic, ethoxylated aliphatics, aromatics, II.,l~,.u~ , or alicyclic groups or any ~ ;.. ,. thereof to which the nitrogen of the N-O group can be attached s or the N-O group is part of these groups. Preferred polyamine N-oxides are those wherein R is a h~,t.u~ , group such as pyridine, pyrrole, imidazole, pyrrolidine, piperidine and derivatiYec thereof.
The N-O group c~n be It~ Lt ;I by the following general structures:
O O
(R1)X--N--(R2)y = N--(Rl)x 1R3)Z
o wherein Rl, R2, R3 are aliphatic, aromatic, heterocyclic or alicyclic groups or ' ' 'nnc thereof; x, y and z are 0 or 1; and the nitrogen of the N-O group can be attached or form part of any of the ~:lfUIr~ d groups. The amine oxide unit o'f the polyamine N-oxides has a pKa <10, preferably pKa <7, more preferred pKa <6.
Any polymer backbone can be used as long as the amine oxide polymer formed is water-soluble and has dye transfer inhibiting properties. Examples of suitable polymeric backbones are polyvinyls, pol~ L,...,~, polyesters, polyethers, polyamide, polyimides, pc~l~t~,lyl~ta and mixtures thereof These polymers include random or block cu,uulr-..~,.a where one monomer type is an amine N-oxide and the other monomer type is an N-oxide. The amine N-oxide polymers typically haYe a ratio of amine to the amine N-oxide of 10:1 to 1:1,000,000. However, the number of amine oxide groups present in the polyamine oxide polymer can be Yaried by ~IJIUIJI;tlL~ UIJOI~ LlUll or by an ~ ~,.u~ L., degree of N-oxidation. The polyamine oxides can be obtained in almost any degree of poly...~,.i~l;o... Typically, the average molecular weight is within the range of 5ûO to 1,000,000; more preferred 2s 1,000 to 500,000; most preferred 5,000 to 100,000.
Copolymers of N ~ ' ' ^ and N--v;,.~" ' ' polymers (referred to as "PVPI") are also preferred for use herein. Preferably the PVPI has an averagemolecular weight range from 5,000 to 1,000,000, more preferably from 5,000 to 200,000, and most preferably from 10,000 to 20,000. (The average molecular weight range is determined by light scattering as described in Barth, et al., kg~
~a~i~, Vol 113. "Modern Methods of Polymer Cl., .~.,lt.;~l;u..", the disclosuresof which are .."u~u~td herein by reference.) The PVPI COpûl~ typically have a molar ratio of N-v;..jl;.l.:d~ to N V~ ' ' from 1:1 to 0.2:1, more preferably from 0.8:1 to 0.3:1, most preferably from 0.6:1 to 0.4:1. These WO g5119953 . . F~ /66 217~267 cùl)ùly~ can be either linear or branched.
The present invention ~ .,-c may also contain a poly~...~l~,~ll, ' ' ("PYP") having an average molecular weight of from about 5,000 to about 400,000,preferably from about 5,000 to about 200,000, an~ more preferably from about 5,000 s to about 50,000. PYP's are known to persons skilled in the detergent field; see, for example, EP-A-262,897 and EP-A-256,696, ;l~cul~u.a~cd herein by reference.
C.~ l o,~ containing PYP can also contain pol~.,L'.jl...., glycol ("PEG") havingan average molecular weight from about 500 to about 100,000, preferably from about 1,000 to about 10,000. Preferably, the ratio of PEG to PYP on a ppm basis delivered in wash solutions is from about 2:1 to about 5û:l, and more preferablyfrom about 3:1 to about 10:1.
(n) Other In~redients - A wide variety of other ingredients useful in detergent ~ ;u ~ can be included in the ~ u~ herein, including other active ingredients, carriers, Iy.l. ul- u~,~,," processing aids, dyes or pigments, perfumes, 15 solvents for liquid rul...ulaL;u.~, solid fillers for bar ~. l.J~ , etc. If high sudsing is desired, suds boosters such as the Clo-C16 ~ r~-~ '' can be u~,u~u~a~cd into the ~.u...~ ., typically at 1%-10% levels. The Clo-C14 ~ ' ' and diethanol amides illustrate a typical class of such suds boosters.
Use of such suds boosters with high sudsing adjunct surfactants such as the amine 20 oxides, betaines and sultaines noted above is also ad~r...L..e,_oua. If desired, soluble magnesium salts such as MgC12, MgSO4, and the like, can be added at levels of, typically, 0.1%-2%, to provide additional suds and to enhance grease removal p.,~ru..
Yarious detersive ingredients employed in the present ..u..l..";l;...,c 2s optionally can be further stabilized by absorbing said ingredients onto a porous ~lJJl~ substrate, then coating said substrate with a l~ uul~l);c coating.
Preferably, the detersive ingredient is admixed with a surfactant before being absorbed into the porous substrate. In use, the detersive ingredient is released from the substrate into the aqueous washing liquor, where it performs its intended 30 detersive fiunction.
To illustrate this technique in more detail, a porous l~ u~ ub;~, silica (trademark SIPERNAT D10, DeGussa) is admixed with a proteolytic enzyme solution containing 3%-5% of C13 15 ethoxylated alcohol (EO 7) nonionic surfactant. Typically, the ~,..,~..,~u.r~ solution is 2.5 X the weight of silica.
35 The resulting powder is dispersed with stirring in silicone oil (various silicone oil viscosities in the range of 500-12,500 can be used). The resulting silicone oil dispersion is emulsified or otherwise added to the final detergent matrix. By this WO 95/19953 2 17 ~ 2 6 ~ F~.l/U~'~ 166 means, ingredients such as the afu~ ;o lf; enzymes, bleaches, bleach activators, bleach catalysts, . photoactivators, dyes, fluorescers, fabric , ' ~ and ~lJdluly~ . surfactants can be "protected" for use in detergents, including liquid laundry detergent, Liquid detergent ~ f.~ can contain water and other solvents as carriers. Low molecular weight primary or secondary alcohols i ,'' i by methanol, ethanol, propanol, and ;50iJIUiJ~Ulvl are suitable. Monohydric aicohols are preferred for s ' ' " _ surfactant, but polyols such as those containing from 2 to about 6 carbon atoms and from 2 to about 6 hydroxy groups (e.g., 1,3-propanediol, 10 ethylene giycol, glycerine, and 1,2~ u~ .,d;ùl) can also be used. The ~.v.,~l,~:l;., may contain &rom 5% to 9û%, typically lû% to 50% of such carriers.
The detergent C..,...l~f~:l;v ~ herein will preferably be formulated such that, during use in aqueous cleaning operations, the wash water will have a pH of between about 6.5 and about 11, preferably between about 7.5 and 10.5. Liquid d;~
15 product r.... ~ "~ preferably have a pH between about 6.8 and about 9Ø
Laundry products are typically at pH 9-11. Techniques for controlling pH at usage levels include the use of buffers, aikalis, acids, etc., and are well known to those skilled in the art.
By "interfaciai tension" ("lFT") herein is meant the tension measured at the 20 oiUwater interface. IFT ~ t~ using the spinning drop technique, are disclosed by Cayias, Schechter and Wade, "The Measurement of Low Interfacial Tension via the Spinning Drop Technique", ACS Symposium Series No. 8 (1975) ADSORPTION AT INTERFACES, beginning at page 234. Equipment for running IFT ...~ is currently available from W. H. Wade, Depts. of Chemistry and Chemical F ~y~ , The University of Texas at Austin, Austin, Texas 78712.
By "low interfacial tension" herein is meant an IFT which is sufficiently low that ~r ,.. I r.-,;.. "~, i.e., rapid ~ with little or no mechanical agitation, can occur. IFT's of about 0.15 dynes/cm, and below, even as low as 0.06 dyneslcm, can easily be secured by the present 1V'''I"~` I;f~"~ at usage 30 levels of 50-20~0ûO ppm.
The ~ ;v~" of greasyloily soils provided by the herein can be simply, but ~,vllv;l~ ly, r~ by admixing a detergent ~ v..~ ;- in accordance with the invention with water. After dissolution of the detergent, a few drops of oil to which a colored oil-soluble dye has been added 35 are added to the detergent solution. With minimal agitation, the entire system appears to take on the color of the dye, due to the dyed oil having been &nely dispersed by the ~ ;r--';f~l effect. This dispersion remains for a WO 95119953 ~17 9 2 t~ 7 r~ J 16~ ~

,".. l.._l,l~ length of time, typically 30 minutes to several hours, even when agitation has stopped. By contrast, with surfactant systems which fail to provide v ~ ;...., the dyed oil droplets produced during agitation rapidly coalesce to fomm one or more relatively large oil globules at the air/water interface.
s More specifically, this ~' dL;u~l of ~ ;nl~ can be conducted as follows.
A consumer relevant test soil is dyed with 0.5% Oil Red EGN. A 100 ml sample of the detergent ~ l;- ,. being tested is prepared at the desired (typically, about 500 ppm) and t~,.l.!J.,.a~ull: in water which is "pre-0 hardened" to any desired Cull~ liOll of calcium ions (typically, about 48 ppm), and contained in an 8 oz. capped jar. The sample pH is adjusted to the intended end-use pH (typically in the range of 6.5 to 10) and 0.2 g of the test soil is added. The jar is shaken 4 times and the sample graded. Altematively, the sample is placed in a beaker and stirred with a stir bar for 15 seconds. The sample is graded as follows:
0 = Clear solution with large red oil droplets in it (û. 1-5 mm diameter), i.e., no ~ :;n 1 = Solution has a definite pink appearance with red oil droplets in it (0.1-1 mm), i.e., slight 2= Solution is dark pink with small red droplets in it, i.e., moderate 20= Solution is red with small red droplets in it (1-200mm), i.e., is substantial;= Solution is dark red with little or no visible droplets (<1-50mm), i.e., r;, Ali,... is complete.
Note: The grading can also be done ~ -AIIY (based on light' The following ~ " illustrate, but are not limiting of, the present invention.
EXAMPLE I
Ste~ 1: Reductive Amination PreDaration of HN~CH2(CHOH)~CH2OH]-(CH2~2-~CH2(CHOH)1CH2OHlNH
About 375 g (about 20 wt% based on amount of glucose used) of Raney Ni (Grace Raney Nickel 4200) is contained in a 2 gallon reactor (316 stainless steel baftled autoclave with DISPERSIMAX hollow shaft multi-blade impeller) 3s pressurized to about 300 psig with hydrogen at room 1~,.",~ u.,:. The nickel bed is covered with water taking up about 10% of the reactor volume This is the first reductive amination run on the present load of nickel catalyst.

21792~7 WO 95/19953 F~l/L,.~. 166 606.53 g of 50 wt% ~LI~ solution in water (5.05 moles, l .00 mole - equiv. of ~LI~ ) jS maintained in a separate reservoir which is in closed ~.. ,... : -l;... with the reactor. The reservoir is pressurized to about 100 psig with nitrogen. 3636.36 g of 55 wt% D-glucose solution in water (11. I moles, 2.20 mole s equiv. of glucose) is maintained in a second separate reservoir which is also in closed c.. , .. :. -1;.. with the reactor and is also pressurized to about 100 psig with nitrogen.
The ~Ll.)' " is loaded into the reactor from the reservoir using a high pressure pump. Once all the eLl~ , r j5 loaded into the reactor, stirring is begun and the reactor heated to 50 deg. C and pressurized to about 500 psig hydrogen.
The glucose solution is then loaded into the reactor from the reservoir using a high pressure pump similar to the amine pump above. However, the pumping rate onthe glucose pump can be varied and on this particular run, it is set to load the glucose in about 10 minutes. Once all the glucose is loaded into the reactor, the pressure is boosted to about 1300 psig hydrogen and the le--l~J.,.dLule raised to 60 deg. C for about I hour. The ~el~ ,.dLul~ is then raised to 70 deg. C for 10 minutes, 80 deg. C
for 10 minutes, 100 deg. C for 10 minutes, and finally 120 deg. C for 5 minutes,while I ~ hydrogen pressure between 1300-1500 psig.
The reactor is then cooled to 70 deg. C and the reaction solution removed from the reactor under hydrogen pressure via an internal dip tube and through a filter in closed ~ ;. .. with the reactor. Filtering under hydrogen pressure allows removal of any nickel particles without nickel dissolution.
Solid product is recovered by ~ JuldL;~m of water. The product purity is dIJI~ LeI.Y 85-90%. Sorbitol is the major impurity at about 10%. The product canbe used as is or purified to greater than 99%.
Step 2: Am;dat;gn ~ ~val a~ .. of CH3(cH2~8c(o~NrcH;i~(cHoH)lcH2QH-]-(cH~
rcH2(cHoH~lcH2oH]Nc(o)(cH2~8cH3 102.13 g of the disugar diamine product of Step I (0.263 moles) is dissolved in a solvent mixture of 295 .16 g of water and 272.3 5 g of acetone. With good mixing, 110.32 g of decanoyl chloride (0.578 moles) is slowly added (approx. I
.1,~,~/ ') to the disugar diamine solution while ~:.,".1l O ~ly adding 10 wt%
NaOH solution to maintain pH 9-11 throughout the reaction. Once all decanoyl chloride is added, the pH is adjusted to dlJIJl u~d~ldtely 10 and the reaction is mixed for one hour.
Solid, crude product is obtained by C~ IdL;~ of water and acetone. The W0 95/19953 ' ~ r~ /66 2~792~7 32 solid, crude product is dissolved in ethanol and the solution filtered to remove NaCI.
The filtrate is then cu.,.,.-,L-G~d to obtain solid, salt free, crude product. The product purity is ~ ,lu7dllldt._1~ 80-90%. The crude product can be used as is.
EXA~LE 11 Step 1: Reductive~minAtinn preraration of HNrcH2(cHoH)lcH2oH~-(cH-l3-o-(cH2)--o-(cH2 rcH2tcHoH) ~CH20H~NH:
1,2-Bis(3-~ , u~Ju~)~,~llal~. ând glucose are reacted in the same manner as Step I of Example I for Reductive amination to produce the disugar diamine 0 product.
Step 2: A~midatiûn Preparation of CH3(cH2)6c(o)NrcH2(cHoH)AcH2oH~-(cH2l3 (CH2)2-O-(CH2~-rCH2tCHOH)lCH 70H]NC(O)(CH2)6CH3 312.12 g ofthe disugar diamine product of Step I (0.618 moles) is melted s under nitrogen and then dehydrated under vacuum. With good mixing, 27.35 g of propylene glycol and 234.92 g of methyl octanoate (1.48 moles), which are preheated to 130 deg. C, are added to the melted diamine. Reaction ~ Lu.c is adjusted to 130 deg. C and 14.0 g of 25 wt% sodium methoxide (0.0618 moles) solution in methanol is added. Once reaction is 1~ 7. o~c, the ~ Lul~ is dropped to 90-100 deg. C and the reaction methanol is refluxed for 1-2 hours. After refluxing, the methanol is distilled out with the last remaining methanol being pulled out under vacuum for two hours. Reaction is poured out and allowed to cool to room L~,IIIIJ", A Lul 1:.
The crude product is a viscous liquid with a purity of 70-80% which can be used an is or purified by column ~,luu ~y,AL~
Examples III - VI
Liquid .~ .u~ which are especially suitable for "light-duty" use, such as for d;ahw~ alu~g, are prepared having the following ;."5.~ "
% By Weight of the Total Cnmr~l~itinn III IV V VI
C12-C14 alkyl ethoxy sulphate 9.30 9.3û 15 9 30 C12 alkyl N-methyl glucamide 6.98 6.98 - 6.98 C12-C14 alkyl l,albu~kl~ 3.48 3.48 - 3.48 C12-C14 alkyl dimethyl betaine l.SS l.SS 2 1.55 C12/14 dimethyl amine oxide 1.16 1.16 2 1.16 C16 dimethyl amine oxide 3.88 ?.7s 5 Gemini arnide (frorn Ex. II) 3.88 3.88 S 7.75 WO 95/19953 ~ 1 7 9 2 67 P ~ 766 C l l alkyl ethoxylate (ave 9) 3 .48 3 .48 4 3 .48 Ca~ 0.14 0.14 0.15 0.14 Mg++ 0.47 0.47 0.5 0.47 Sodium cumene sulphonate 3.7 3.7 3.7 3 7 EtOH 3 3 3 3 EXAMP!.F. Vll A granular detergent u"-l~v~ J . comprising a non-,ullv~ ulu~ builder 5 system is as follows:
In~redient % ~wt.
Oleoyl Sarcosinate, Na 8.0 Tallowalkyl Sulfate, Na 2.5 Gemini amide (&om Ex. II) 5.0 C12 14Tlul,~ ' Chloride 1.2 Zeolite A (1-10 IIU~,IUII~ I) 23 Maleic/Acrylic Copolymer 5.0 Sodium ~e.l,~ub~ 12 Sodium Carbonate 10.6 Sodium Silicate (2.0) 5 0 Glycerol 0 5 Savinase (enzyme) 1.6 Silicone (suds suppressor) 0 5 Water, Perfume, Minors Balance EX~LF VITT
The '"l"~;" of Example VII is modified by replacing the sodium uI,u"~ with an equivalent amount of sodium perborate. In an altemate mode, all or part of the TAED bleach activator can be replaced by NOBS bleach activator.
EXAMPLE IX
A granular detergent ~ with fabric softening properties comprising a mixed, non-pl,v~,l,ùlu~ builder system is as follows:
In~redient % (wt.) Gemini amide (from Ex. II) 8.0 C 14 15 Alkyl Sulfate, Na 3 .0 Sodium Citrate 5 0 Zeolite A (1-10 """, u.. ~ ,) 2û.0 WO 95/19953 1 ~ 66 ~79267 :! `q' ' 34 Sodium Pc.. ,vv.. ~l~, 18.0 TAED/NOBS (1:1) 5.0 Sodium Sulfate 12.0 Sodium Silicate 5.0 SC12 14 Dimethyl aI~d-vA~,Lllyl) Ammonium Chloride 1.S
rvly~ yl~t~, (mw4000-5000) 3 0 Hydrogen Tallow Fatty Acid 0.5 CAREZYME 0.9 10TERMAMYL 0.75 Optical Brightener 0.2 Moisture, Minors Balance EXAMPLE X
In the ~u...~ ;., of Example IX the Zeolite A may be replaced by an 15 equivalent amount of SKS-6. In an alternate mode, the alkyl sulfate can be replaced by a Cll_14 alkyl benzene sulfonate surfactant and/or by oleoyl sarcosinate surfactant.
EXAMPLE ~I
A granular ~ v~ , comprises the following ingredients.
~o ~ % (wt.) Gemini amide (from Ex. II) 19.0 Zeolite A (1-10 microns) 25.0 Sodium Citrate 3.0 Sodium rel~.l 12.0 25Pvl~ u LaLc 5.0 EDDS 3.0 Protease I o Lipase 1.0 TAED 5 o 30Sodium Carbonate lo.o Sodium Silicate 3.0 Water and Minors Balance EXA~J.F. XII
The ~ v, ~ ~ of Example Xl is modified by reducing the Gemini amide to 35 17% of the ~ and adding 2% by weight of " yl ethoxylate (1-5 avg. ethoxylate) as NEODOL.

wo 95119953 2~ t 7 9 2 6 7 E ~ l/ u..,~ ~ /66 EXAMPLE XIII
A detergent bar is prepared by c~ and extruding a ~.. I.n~
generally according to Example Xl. Where allowed by statute, the ~, builder may be replaced by a phosphate builder such as sodium L~ Gl ylJllO~ L~
EXAMPLE XIV
These granular detergents can be prepared by spray-drying (final product density 520 g/l) or ~pl.,.,...~l;..~ (final product density above 600 g/l) the Base Granule. The remaining dry ingredients are admixed in granular or powder form vith the Base Granule in a rotary mixing drum, and the liquid ingredients (nonionic 0 surfactant and perfume) are sprayed on.
Base Granule A . _ . . C
C alkyl sulfate 5.8 -- --Gemini amide (from Ex. II) 6.0 11.0 6.0 C fatty acid 2.2 -- 2.2 16 .18 s Zeollte A (1-~0 mmcrons) 7.0 7.0 7 0 r~ t~. (4500 MW) 3.3 3.3 3.3 rul.~.,L~ , glycol (8000 MW) 1.3 1.3 1.3 Sodium carbonate 10.7 10.7 10.7 Sodium sulfate 5.0 5.0 5.0 20 Sodium silicate(SiO /Na O=2) 5.0 5.0 5.0 ;~, ,.I' . ,. ,, ,~ 2 2 7. 1 7. 1 7. 1 Admix Zeolite A (1-10 micron) 5.0 5.0 5.0 C -N-(3 ~JIU~.J1) 25 glucamide -- 6.4 --C12 14N-methylglucamide 4.0 -- 4.4 C alkyl sulfate 11.8 --C alkyl ethoxy(2) sulfate -- -- 5.0 C alkyl ethoxy (2.25) sulfate 4.0 --30 Suds suppressor flake~ -- 1.0 0.5 r r .. (filler salts, brightener, enzyme, buffer, zeolite or other builder, etc) 17.2 17.2 16.5 SpraY-on 3s C12 13 alkyl ethoxylate (6.5 EO) 2.0 2.0 2.0 Pe me 0.5 0.5 0.5 Water and " Balance-WO95/19953 ~ ~ 79267 r~ 51 /66 *Suds Suppressor Flake contains a~ u~lllalely 5% of a silicat silicone oil dispersion t(l in a flake containing primarily PEG (8000 MU~), at greater than 80%, and minor optional water soluble ingredients.
The ~,., ,..~`:1;..~` of this example may be modified to forrn a bleach-5 containing ~ by adding sodium ~ ,a~bulla~ (in an amount to provide 12weight percent) and TAED bleach activator (in an amount to provide 4 weight percent). Also, the TAED may be replaced by NOBS bleach activator.
EXA~LE XV
The ~ of Example XIV(A) is modified by the addition of 0.2%
0 (based on final product) CAREZYME (cellulase) in the admix. Alternatively, a 1~
mixture of LIPOLASE (lipase)l cellulase and protease at a total ~veight % of product of 0.9% can be added via the admix.
EXA~LE XVI
The ...,..~ ,.. of Example XIV(B) is modified by the addition of 10%
sodium ~uallJù~la~ (100-SOQ micron) or sodium perborate IllU..VIrlrlldL~ and 1%
~ aa~ yL,.~ or 1% nol~a~vylu7~yb~ sulfonate (based on final product) via the admix to provide a bleaching function.
E~AMPLE XVII
A liquid laundry detergent ~ ''J`;~ herein comprises the following.
In~redient % lwt.
Oleoyl sarcosinate, Na 15.0 Gemini alnide (from Ex. II) 5.0 Sodium citrate 3.0 C alcohol ethoxylate (3) 13.0 M10 1 __1 2.5 MAXATASE (enzyme) 0.5 LIPOLASE (enzyme) 0.5 CaCI I
V.~ u.tl.luuyl.,..e glycoVethanol (100:1:1) Balance E7~AMPLE XVIII
Highly ~ùr.~,~."~ d liquid laundry detergents are as follows.
In~redient % (wt.) Oleoyl all , Na~ 15.0 C EO(2.25) sulfate, Na 15.0 3s Gemini amide (from Ex. II) 10.40 Citric acid 5.0 C12 14 fatty acid 4.00 WO 95119953 ~ 1 7 9 2 6 7 r~l~u . . /66 ELI-U~I~IC~ ICIIU~ e pentamine û.99 Boric acid 2.00 NaOH 3 79 51,2-~,.. ,y~ul.,d;~l 9.15 Ethanol 6.55 Ml ' -' - 1.05 Sodium cumene sulfonate 3.96 H2O/minors Balance 10pH 10% aq. solution 8.29 ~Potassium, ammonium or ~I ' ' salts may also be used.

Claims (7)

WHAT IS CLAIMED IS:

1. Novel gemini polyhydroxy fatty acid amide compounds having the formula:
wherein: X is a bridging group having from 2 to 200 atoms; Z and Z' are the same or different alcohol-containing moieties having two or more hydroxyl groups, or one of Z
or Z' is hydrogen; and R and R? are the same or different hydrocarbyl moieties having from 1 to 21 carbon atoms and can be saturated, branched or unsaturated and mixtures thereof.

2. A compound according to Claim 1 wherein X is selected from the group consisting of substituted or unsubstituted, branched or linear alkyl, ether alkyl, amino alkyl, or amido alkyl moieties having from 2 to 15 carbon atoms; and Z and Z' are independently selected from the group consisting of polyhydroxyhydrocarbyl moieties having a linear hydrocarbyl chain with at least 2 hydroxyl directly connected to the chain, or an alkoxylated derivative thereof.

3. A compound according to Claim 1 wherein X is selected from the group consisting of unsubstituted, linear alkyl moieties having the formula -(CH2)n-, wherein n is an integer from 2 to 15, unsubstituted, branched alkyl moieties having from 2 to 15 carbon atoms, unsubstituted, branched or linear ether alkyl moieties having the formula -R2-(O-R2)m-, wherein each R2 is independently selected from C2-C8 branched or linear alkyl or aryl moieties and m is an integer from 1 to 5, unsubstituted, branched or linear amino or amido alkyl moieties having the formula -R2-(N(R3)-R2)m-, wherein each R2 is independently selected from C2-C8 branched or linear alkyl or aryl moieties, m is an integer from 1 to 5, R3 is selected from hydrogen, C1-C5 alkyl, and -C(O)R4-, wherein R4 is C1-C21 alkyl; Z and Z' are independently selected from the group consisting of-CH2-(CHOH)-p-CH2OH, -CH(CH2OH)-(CHOH)p-?-CH2OH, -CH2-(CHOH)2(CHOR1)(CHOH)-CH2OH, where p is an integer from 1 to 5, inclusive, and R1 is H or a cyclic mono- or polysaccharide, and alkoxylated derivatives thereof; and R
and R' are independently selected from the group consisting of straight or branched chain C3-C13 alkyl or alkenyl moieties.

4. A compound according to Claim 1 wherein X is selected from the group consisting of -(CH2)2-, -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -CH2CH(CH3)(CH2)3-, -(CH2)2-O-(CH2)2-, -(CH2)3-O-(CH2)3-, -(CH2)2-O-(CH2)3-, -(CH2)2-O -(CH2)2-O-(CH2)2-, -(CH2)3-O-(CH2)2-O-(CH2)3-, -(CH2)2-O-(CH2)3-O-(CH2)2-, -(CH2)2-NH-(CH2)2-, -(CH2)3-NH-(CH2)3-, -(CH2)2-NH-(CH2)3-, -(CH2)2-N(C(O)R)-(CH2)2-, -(CH2)3-N(C(O)R)-(CH2)3-, -(CH2)2-N(C(O)R)-(CH2)3-, -(CH2)2-NH(C6H4)NH-(CH2)2-, -(CH2)3-NH(C6H4)NH-(CH2)3-, -(CH2)2-NHCH2(C6H4)CH2NH-(CH2)2-. -(CH2)3-NHCH2(C6H4)CH2NH-(CH2)3-; Z and Z' are independently selected from the group consisting of-CH2-(CHOH)4-CH2OH; and R and R' are independently selected from the group consisting of straight chain C5-C11 alkyl or alkenyl moieties.

5. Compositions comprising:
(a) at least 0.1% of a gemini polyhydroxy fatty acid amide compound according to Claims 1, 2, 3 or 4; and (b) at least 0.1% of one or more laundry or personal care composition materials.

6. A method for laundering fabrics or cleaning hard surfaces, comprising contacting said fabrics or hard surfaces with an aqueous solution containing at least 10 ppm of a gemini polyhydroxy fatty acid amide surfactant according to Claims 1, 2, 3 or 4.

7. A method for laundering fabrics or cleaning hard surfaces, comprising contacting said fabrics or hard surfaces with an aqueous solution containing at least 10 ppm of a composition comprising a gemini polyhydroxy fatty acid amide surfactant according to Claim 5.