Compositions comprising glyceroglycolipids having an ether linkage as a surfactant or cosurfactant

The present invention relates to detergent compositions comprising a glyceroglycolipid having one or two ether linkages for use as a surfactant or cosurfactant in the detergent compositions.

BACKGROUND OF THE INVENTION 
The present invention relates to novel detergent or novel personal product 
compositions comprising glyceroglycolipids having an ether linkage as 
surfactants or cosurfactants in the compositions. In particular, the 
glyceroglycolipid compounds are compounds having 1 to 4 saccharide units. 
Natural glycolipids are known in the art and these structures have been 
elucidated. The term glycolipid refers to any of a class of lipids that, 
upon hydrolysis, yield a sugar (e.g., galactose or glucose), and a lipid 
(e.g. substituted glycerol group). One major class of these glycolipids 
belong to the glycero glycolipids, i.e., a, glycolipid based around a 
glycerol frame structure. For example, the compound may have a sugar 
structure at one end of the glycerol structure instead of an --OH group 
and an ester linkage at one or both of the other --OH groups that would 
normally be found on glycerol. 
U.S. Pat. No. 3,729,461 to Pomeranz et al., for example, teaches mono- and 
di-galactosyl glyceride compounds isolated from wheat flour. On one end of 
the glycerol frame is found a sugar group (i.e., the mono- or 
di-saccharide group) and the two other OH groups normally found on a 
glycerol are esterified. 
In Kobayashi et al., J. Chem Soc. Perkin., Trans. p. 101-103 (1989), there 
are again taught mono-and di-galactosyl diacylglycerols similar to chose 
taught in Pomeranz et al. Again, there is a sugar group on one end and a 
mono- or diester where the remaining two --OH groups on a glycerol would 
normally be found. 
Other ester functionalized mono- and diacyl galactosylglycerols are taught 
in Baruah et al., Phytochemistry, 22(8):1741-1744 (1983) and in U.S. Pat. 
No. 4,859,589 to Godfretsen et al. 
As mentioned above, the above references disclose only ester-functionalized 
glyceroglycolipids. 
Williams et al. Archives of Biochemistry and Biophysics, 195(1):145-151 
(1979) teach certain alkyl bionamide compounds which are formed by linking 
aldobionic acids to an alkylamine through an amide bond. The compounds of 
the invention contain no such amide bond. 
U.S. Pat. No. 4,011,169 to Diehl et al. teaches enzyme containing 
compositions comprising certain aminated polysaccharides as stabilizing 
agents for the enzymes. First this reference relates to an amine linkage 
rather than an ether linkage. Further, it is clear from this reference 
that the polysaccharides used have at the very least 5 or more saccharide 
units and preferably, well over 100 (the application notes at column 7, 
line 50-52, that natural polysaccharides that are smaller than this are 
rare). Further there is a limitation as to the amount of elemental 
nitrogen to to the compound and it seems that compounds with fewer 
saccharide units would not meet this limitation. 
A glyceroglycolipid containing an ether linkage (where the --OH group on 
the glycerol would normally be found) is disclosed in Coulon-Moulec, Bull. 
Soc. Chem. Biol., 49(7):825-840 (1967) and in Alvarez et al. , J. Lipid 
Res., 31(6) :1073-1081 (1990) . 
These references are concerned, however, only with the synthesis of various 
lipid glycosides and contains absolutely no teaching or suggestion that 
glyceroglycolipids having an ether linkage can be used as surfactants or 
cosurfactants in detergent or personal product compositions. 
EP No. 232,851-A (Assigned to National Starch) also appears to teach a 
glycceroglycolipid with an ether linkage. However, this reference is 
clearly concerned with compounds used as paper strength additives and 
neither teaches nor suggests that these compounds may be used as 
surfactants in detergent or personal product compositions. 
U.S. Pat. No. 4,804,497 teaches a glycoside surfactant for enhancing the 
antistatic effects of certain quaternary ammonium surfactants. There is 
absolutely no teaching or suggestion that the surfactant can be used alone 
or in combination with other surfactants to enhance detergency. 
Specifically although Table A at columns 5-6 talks about cleaning 
performance, there is no teaching of how results were reached or against 
what it was tested. This is not surprising since the reference is 
concerned with softening, not detergency and evaluates primary how the 
surfactant and cosurfactant affect static charge build up. 
Finally, because the compounds of the invention are derived from naturally 
occurring carbohydrates, the use of these compounds can provide a source 
of renewable raw materials that are synthetically versatile and 
environmentally friendly. 
Accordingly, it is an object of this invention to provide novel surfactants 
and cosurfactants derived from carbohydrates for use in detergent and 
personal product compositions. More particularly, it is an object of the 
invention to provide compositions comprising these biodegradable 
surfactants. 
SUMMARY OF THE INVENTION 
The present invention relates to detergent and personal product 
compositions comprising a glyceroglycolipid having one or two ether 
linkages for use as a surfactant or cosurfactant in the compositions. In 
particular the glyceroglycolipid has the following formula: 
##STR1## 
wherein A.sup.1 is a saccharide, preferably having one to four saccharide 
units, more preferably a mono or disaccharide, and R or R.sup.1 are the 
same or different and represent a hydrogen, a straight chained or 
branched, saturated or unsaturated hydrocarbon radical (including aryl, 
arene, etc.) having 1 to 24, preferably 6 to 18, carbons; or an acyl group 
except that R and R.sup.1 cannot both be hydrogen (i.e. must be at least 
one ether linkage).

DETAILED DESCRIPTION OF THE INVENTION 
The present invention provides detergent and personal product compositions 
comprising, as a surfactant or cosurfactant, a glyceroglycolipid compound 
having the structure set forth below: 
##STR2## 
wherein A.sup.1 is a saccharide, preferably having one to four saccharide 
units, more preferably a mono- or disaccharide, and most preferably a 
monosaccharide such as glucose or galactose; and 
R or R.sup.1 are hydrogen, a branched or unbranched, saturated or 
unsaturated hydrocarbon radical having from about 1 to about 24, 
preferably from about 6 to about 18 carbons or an acyl group, except that 
R and R.sup.1 cannot both be hydrogen at the same time. 
In a preferred embodiment of the invention, A.sup.1 is a monosaccharide 
and, in particular, is a galactoside (e.g., D-galactoside), R.sup.1 is 
hydrogen and R is a C.sub.12 alkyl chain. 
These examples of compounds of the invention (having varying R or A.sup.1 
groups) are set forth below: 
3-(butyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(pentyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(hexyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(heptyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(octyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(nonyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(decyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(dodecyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(tetradecyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(hexadecyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(octadecyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(eicosyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(docosyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(tetracosyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(hexenyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(decenyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(dodecenyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(tetradecenyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(hexadecenyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(octadecenyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(docosenyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(tetracosenyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(3-oxa-tridecyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(fluorododecyloxy)-2-hydroxypropyl-.beta.-D-Galactopyranoside 
3-(butyloxy)-2-hydroxypropyl-.beta.-D-Glucopyranoside 
3-(octyloxy)-2-hydroxypropyl-.beta.-D-Mannopyranoside 
3-(tetradecyloxy)-2-hydroxypropyl-.beta.-D-lactoside 
3-(octadecyloxy)-2-hydroxypropyl-.beta.-D-maltoside 
3-(octyloxy)-2-hydroxypropyl-.beta.-D-galactotrioside 
3-(dodecyloxy)-2-hydroxypropyl-.beta.-D-cellotrioside 
SYNTHESIS 
The glyceroglycolipid of the invention is formed from a precursor having an 
epoxide group at the location where the ether linkage is formed and having 
a sugar group. The sugar may be protected or unprotected. An example of 
such a precursor would be the galactose epoxide compound having the 
structure: 
##STR3## 
Once the protected epoxide galactose compound is obtained, this can be 
reacted with an alcohol ROH (wherein R represents the desired chain length 
of the alkyl group forming the ether linkage) desirably in the presence of 
a Lewis acid catalyst such as zinc chloride or stannic chloride; or in the 
presence of a cationic radical generator such as 2,3-dichloro-5,6-dicyano 
benzoquinone (ddq) to form the desired glyceroglycolipid with ether 
linkage. 
The epoxide precursor used to form the desired surfactant can in turn be 
formed in a variety of ways. 
For example, a galactose epoxide compound may be synthesized enzymatically 
via the hydrolysis of lactose in the presence of allyl alcohol and 
.beta.-galactosidase to form a allyl-.beta.-D-galactopyranoside which can 
then be protected and oxidized to the corresponding epoxide with 
m-chloroperoxybenzoic acid (m-CPBA) in dichloromethane. This type of 
reaction, which is taught in Nilsson, K.G.I., Carbohydrate Research, 
180:53-59 (1988) is set forth below: 
##STR4## 
A chemical mode for preparation of the galactose epoxide involves the use 
of acetobromogalactose (2,3,4,6-tetra-O-acetyl-.alpha.-D-galactopyranosyl 
bromide) mixed with allyl alcohol with mercuric cyanide. This simple 
Koenigs-Knorr glycosydation affords the allyl-.beta.-D-galactopyranoside 
tetraacetate in very good yield. Oxidation with peracide gives the 
protected epoxide sugar. 
##STR5## 
Once the epoxide precursor is formed, as discussed above, the epoxide ring 
is opened and OH groups are regenerated from the acetylated groups via 
hydrolysis. 
COMPOSITIONS 
The surfactants of the invention may be used in cleansing or detergent 
composition such as heavy duty liquid detergents (generally enzyme 
containing) or powdered detergents. Examples of liquid or powdered 
detergents are described in U.S. Pat. No. 4,959,179 to Aronson (for liquid 
detergent compositions) and U.S. Pat. No. 4,929,379 to Oldenburg et al. 
(for powdered detergent compositions), both of which are incorporated 
herein by reference. 
The liquid detergent compositions of the invention may be built or unbuilt 
and may be aqueous or nonaqueous. The compositions generally comprise 
about 5%-70% by weight of a detergent active material and from 0% to 50% 
of a builder. 
The composition may comprise 5-70% entirely the surfactant of the invention 
or it may comprise a mixture of surfactants wherein the surfactant of the 
invention comprises 40 to 80% of the mixture, preferably 50 to 70% of the 
mixture. The liquid detergent compositions of the invention may further 
comprise an amount of electrolyte (defined as any water-soluble salt) 
whose quantity depends on whether or not the composition is structured. By 
structured is meant the formation of a lamellar phase sufficient to endow 
solid suspending capability. 
More particularly, while no electrolyte is required for a non-structured, 
non-suspending composition, at least 1%, more preferably at least 5% by 
weight and most preferably at least 15% by weight electrolyte is used. The 
formation of a lamellar phase can be detected by means well known to those 
skilled in the art. 
The water-soluble electrolyte salt may be a detergency builder, such as the 
inorganic salt sodium tripolyphosphate or it may be a non-functional 
electrolyte such as sodium sulphate or chloride. Preferably, whatever 
builder is used in the composition comprises all or part of the 
electrolyte. 
The liquid detergent composition generally further comprises enzymes such 
as proteases, lipases, amylases and cellulases which, when present, may be 
used in amounts from about 0.01 to 5% of the compositions. Stabilizers or 
stabilizer systems may be used in conjunction with enzymes and generally 
comprise from about 0.1 to 15% by weight of the composition. 
The enzyme stabilization system may comprise calcium ion, boric acid, 
propylene glycol and/or short chain carboxylic acids. The composition 
preferably contains from about 0.01 to about 50, preferably from about 0.1 
to about 30, more preferably from about 1 to about 20 millimoles of 
calcium ion per liter. 
When calcium ion is used, the level of calcium ion should be selected so 
that there is always some minimum level available for the enzyme after 
allowing for complexation with builders, etc., in the composition. Any 
water-soluble calcium salt can be used as the source of calcium ion, 
including calcium chloride, calcium formate, calcium acetate and calcium 
propionate. A small amount of calcium ion, generally from about 0.05 to 
about 2.5 millimoles per liter, is often also present in the composition 
due to calcium in the enzyme slurry and formula water. 
Another enzyme stabilizer which may be used is propionic acid or a 
propionic acid salt capable of forming propionic acid. When used, this 
stabilizer may be used in an amount from about 0.1% to about 15% by weight 
of the composition. 
Another preferred enzyme stabilizer is polyols containing only carbon, 
hydrogen and oxygen atoms. They preferably contain from 2 to 6 carbon 
atoms and from 2 to 6 hydroxy groups. Examples include propylene glycol 
(especially 1,2 propanediol which is preferred), ethylene glycol, 
glycerol, sorbitol, mannitol and glucose. The polyol generally represents 
from about 0.5% to about 15%, preferably from about 1.0% to about 8% by 
weight of the composition. 
The composition herein may also optionally contain from about 0.25% to 
about 5%, most preferably from about 0.5% to about 3% by weight of boric 
acid. The boric acid may be, but is preferably not, formed by a compound 
capable of forming boric acid in the composition. Boric acid is preferred, 
although other compounds such as boric oxide, borax and other alkali metal 
borates (e.g. sodium ortho-, meta- and pyroborate and sodium pentaborate) 
are suitable. Substituted boric acids (e.g., phenylboronic acid, butane 
boronic acid and a p-bromo phenylboronic acid) can also be used in place 
of boric acid. 
On especially preferred stabilization system is a polyol in combination 
with boric acid. Preferably, the weight ratio of polyol to boric acid 
added is at least 1, more preferably at least about 1.3. 
With regard to the detergent active, the detergent active material may be 
an alkali metal or alkanolamine soap or a 10 to 24 carbon atom fatty acid, 
including polymerized fatty acids, or an anionic, a nonionic, cationic, 
zwitterionic or amphoteric synthetic detergent material, or mixtures of 
any of these. 
Examples of the anionic synthetic detergents are salts (including sodium, 
potassium, ammonium and substituted ammonium salts) such as mono-, di- and 
triethanolamine salts of 9 to 20 carbon alkylbenzenesulphonates, 8 to 22 
carbon primary or secondary alkanesulphonates, 8 to 24 carbon 
olefinsulphonates, sulphonated polycarboxylic acids prepared by 
sulphonation of the pyrolyzed product of alkaline earth metal citrates, 
e.g., as described in British Patent specification, 1,082,179, 8 to 22 
carbon alkylsulphates, 8 to 24 carbon alkylpolyglycol-ether-sulphates, 
-carboxylates and -phosphates (containing up to 10 moles of ethylene 
oxide); further examples are described in "Surface Active Agents and 
Detergents" (vol. I and II) by Schwartz, Ferry and Bergh. Any suitable 
anionic may be used and the examples are not intended to be limiting in 
any way. 
Examples of nonionic synthetic detergents which may be used with the 
invention are the condensation products of ethylene oxide, propylene oxide 
and/or battalion oxide with 8 to 18 carbon alkylphenols, 8 to 18 carbon 
fatty acid amides; further examples of nonionics include tertiary amine 
oxides with 8 to 18 carbon alkyl chain and two 1 to 3 carbon alkyl chains. 
The above reference also describes further examples of nonionics. 
The average number of moles of ethylene oxide and/or propylene oxide 
present in the above nonionics varies from 1-30; mixtures of various 
nonionics, including mixtures of nonionics with a lower and a higher 
degree of alkoxylation, may also be used. 
The nonionic may also be a sugar amide such as a polysaccharide amide. 
Specifically, the surfactant may be one of the lactobionamides described 
in the Ser. No. 816,419 to Au et al., hereby incorporated by reference; or 
it may be a polyhydroxy sugar amide such as, for example, those described 
in U.S. Pat. No. 5,009,814 to Kelkenberg, hereby incorporated by reference 
into the subject application. 
Examples of cationic detergents which may be used are the quaternary 
ammonium compounds such as alkyldimethylammonium halogenides. 
Examples of amphoteric or zwitterionic detergents which may be used with 
the invention are N-alkylamine acids, sulphobetaines, condensation 
products of fatty acids with protein hydrolysates; but owing to their 
relatively high costs they are usually used in combination with an anionic 
or a nonionic detergent. Mixtures of the various types of active 
detergents may also be used, and preference is given to mixtures of an 
anionic and a nonionic detergent active. Soaps (in the form of their 
sodium, potassium and substituted ammonium salts) of fatty acids may also 
be used, preferably in conjunction with an anionic and/or nonionic 
synthetic detergent. 
Builders which can be used according to this invention include conventional 
alkaline detergency builders, inorganic or organic, which can be used at 
levels from 0% to about 50% by weight of the composition, preferably from 
1% to about 20% by weight, most preferably from 2% to about 8%. 
Examples of suitable inorganic alkaline detergency builders are 
water-soluble alkalimetal phosphates, polyphosphates, borates, silicates 
and also carbonates. Specific examples of such salts are sodium and 
potassium triphosphates, pyrophosphates, orthophosphates, 
hexametaphosphates, tetraborates, silicates and carbonates. 
Examples of suitable organic alkaline detergency builder salts are: (1) 
water-soluble amino polycarboxylates, e.g., sodium and potassium 
ethylenediaminetetraacetates, nitrilotriacetates and 
N-(2-hydroxyethyl)-nitrilodiacetates; (2) water-soluble salts of phytic 
acid, e.g., sodium and potassium phytates (see U.S. Pat. No. 2,379,942); 
(3) water-soluble polyphosphonates, including specifically, sodium, 
potassium and lithium salts of ethane-1-hydroxy-1,1-diphosphonic acid; 
sodium, potassium and lithium salts of methylene diphosphonic acid; and 
sodium, potassium and lithium salts of ethane-1,1,2-triphosphonic acid. 
Other examples include the alkali methal salts of 
ethane-2-carboxy-1,1-diphosphonic acid hydroxymethanediphosphonic acid, 
carboxylidiphosphonic acid, ethane-1-hydroxy-1,1,2-triphosphonic acid, 
ethane-2-hydroxy-1,1,2-triphosphonic acid, propane-1,1,3,3-tetraphosphonic 
acid, propane-1,1,2,3-tetraphosphonic acid, and 
propane-1,2,2,3-tetraphosphonic acid; (4) water soluble salts of 
polycarboxylate polymers and copolymers as described in U.S. Pat. No. 
3,308,067. 
In addition, polycarboxylate builders can be used satisfactorily, including 
water-soluble salts of mellitic acid citric acid, and 
carboxymethyloxysuccinic acid and salts of polymers of itaconic acid and 
maleic acid. Specific polycarboxylate builders include DPA (dipicolinic 
acid) and ODS (oxydisuccinic acid). Certain zeolites or aluminosilicates 
can be used. One such aluminosilicate which is useful in the compositions 
of the invention is an amorphous water-insoluble hydrated compound of the 
formula Na.sub.x (.sub.y A10.sub.2.SiO.sub.2), wherein x is a number from 
1.0 to 1.2 and y is 1, said amorphous material being further characterized 
by a Mg++exchange capacity of from about 50mg eq. CaCO.sub.3 /g. and a 
particle diameter of from about 0.01 micron to about 5 microns. This ion 
exchange builder is more fully described in British Pat. No. 1,470,250. 
A second water-insoluble synthetic aluminosilicate ion exchange material 
useful herein is crystalline in nature and has the formula Na.sub.z 
[(A10.sub.2).sub.y.(SiO.sub.2)]xH.sub.2 O, wherein z and y are integers of 
at least 6; the molar ratio of z and y is in the range from 1.0 to about 
0.5, and x is an integer from about 15 to about 264; said aluminosilicate 
ion exchange material having a particle size diameter from about 0.1 
micron to about 100 microns; a calcium ion exchange capacity on an 
anhydrous basis of at least about 200 milligrams equivalent of CaCO.sub.3 
hardness per gram; and a calcium exchange rate on an anhydrous basis of at 
least about 2 grams/gallon/minute/gram. These synthetic aluminosilicates 
are more fully described in British Pat. No. 1,429,143. 
In addition to the ingredients described hereinbefore, the preferred 
compositions herein frequently contain a series of optional ingredients 
which are used for the known functionality in conventional levels. While 
the detergent compositions are generally premised on aqueous, 
enzyme-containing detergent compositions, it is frequently desirable to 
use a phase regulant. This component together with water constitutes then 
the solvent matrix for the claimed liquid compositions. Suitable phase 
regulants are well-known in liquid detergent technology and, for example, 
can be represented by hydrotropes such as salts of alkylarylsulfonates 
having up to 3 carbon atoms in the alkylgroup, e.g., sodium, potassium, 
ammonium and ethanolamine salts of xylene-, toluene-, ethylbenzene-, 
cumene-, and isopropylbenzene sulfonic acids. Alcohols may also be used as 
phase regulants. This phase regulant is frequently used in an amount from 
about 0.5% to about 20%, the sum of phase regulant and water is normally 
in the range from 35% to 65%. 
The preferred compositions herein can contain a series of further optional 
ingredients which are mostly used in additive levels, usually below about 
5%. Examples of the like additives include: polyacids, suds regulants, 
opacifiers, antioxidants, bactericides, dyes, perfumes, brighteners and 
the like. 
The beneficial utilization of the claimed compositions under various usage 
conditions can require the utilization of a suds regulant. While generally 
all detergent suds regulants can be utilized, preferred for use herein are 
alkylated polysiloxanes such as dimethylpolysiloxane, also frequently 
termed silicones. The silicones are frequently used in a level not 
exceeding 0.5%, most preferably between 0.01% and 0.2%. 
It can also be desirable to utilize opacifiers inasmuch as they contribute 
to create a uniform appearance of the concentrated liquid detergent 
compositions. Examples of suitable opacifiers include: polystyrene 
commercially known as LYTRON 621 manufactured by Monsanto Chemical 
Corporation. The opacifiers are frequently used in an amount from 0.3% to 
1.5%. 
The compositions herein can also contain known antioxidants for their known 
utility, frequently radical scavengers in the art established levels, 
i.e., 0.001% to 0.25% (by reference to total composition). 
When the liquid composition is an aqueous composition, the balance of the 
formulation consists of an aqueous medium. When it is in the form of a 
nonaqueous composition, the above ingredients make up for the whole 
formulation (a nonaqueous composition may contain up to 5% water). 
An ideal liquid detergent composition might contain (all percentages by 
weight ): 
(1) 5-70% detergent active system; 
(2) 0-50% builder; 
(3) 0-40% electrolyte 
(4) 0.01-5% enzyme; 
(5) 0.1-15% enzyme stabilizer; 
(6) 0-20% phase regulant; and 
(7) remainder water and minors 
The detergent composition of the invention might also be a powdered 
detergent composition. 
Such powdered compositions generally comprise from about 5-40% of a 
detergent active system which generally consists of an anionic, a nonionic 
active, a fatty acid soap or mixtures thereof; from 20-70% of an alkaline 
buffering agent; up to about 40% builder and balance minors and water. 
The alkaline buffering agent may be any such agent capable of providing a 
1% product solution with a pH of above 11.5 or even 12. Advantageous 
alkaline buffering agents are the alkalimetal silicates, as they decrease 
the corrosion of metal parts in washing machines, and in particular sodium 
orthometa- or di-silicates, of which sodium metasilicate is preferred. The 
alkaline buffering agent is present in an amount of from 0 to 70% by 
weight, preferably from 0 to 30% by weight. 
In addition the compositions of the invention can and normally will contain 
detergency builders in an amount of up to 40% by weight and preferably 
from 5 to 25% by weight of the total composition. 
Suitable builders include sodium, potassium and ammonium or substituted 
ammonium pyro- and tri-polyphosphates, -ethylene diamine tetraacetates, 
-nitrilotriacetates, -etherpolycarboxylates, -citrates, -carbonates, 
-orthophosphates, -carboxymethyloxysuccinates, etc. Specific builders 
include DPA and ODS. Also less soluble builders may be included, such as 
e.g., an easily dispersible zeolite. Particularly preferred are the 
polyphosphate builder salts, nitrilotriacetates, citrates, 
carboxymethyloxysuccinates and mixtures thereof. 
Other conventional materials may be present in minor amounts, provided they 
exhibit a good dissolving or dispersing behavior; for example sequestering 
agents, such as ethylenediamine tetraphosphonic acid; soil-suspending 
agents, such as sodiumcarboxymethylcellulose, polyvinylpyrrolidone or the 
maleic anhydride/vinylmethylether copolymer, hydrotropes; dyes; perfumes; 
optical brighteners; alkali-stable enzymes; germicides; anti-tarnishing 
agents; lather depressants; fabric softening agents; oxygen- or 
chlorine-liberating bleaches, such as dichlorocyanuric acid salts or 
alkalimetal hypochlorides. 
The remainder of the composition is water. 
An ideal powdered detergent composition might contain the following (all 
percentages by weight): 
(1) 5-40% detergent active system; 
(2) 0-40% builder; 
(3) 0-30% buffer salt; 
(4) 0-30% sulfate; 
(5) 0-20% bleach system; 
(6) 0-4% enzyme; and 
(7) Minors plus water to 100% 
The surfactants of the invention may also be used in personal product 
compositions such as, for example, soap bar compositions, facial or body 
cleansing compositions, shampoos for hair or body, conditioners, cosmetic 
compositions or dental compositions. 
In one embodiment of the invention, the surfactant of the invention may be 
used, for example, in a toilet bar (i.e., soap and/or detergent bar) 
formulation. 
Typical toilet bar compositions are those comprising fatty acid soaps used 
in combination with a detergent other than fatty acid soap and free fatty 
acids. It should be noted that the composition may comprise no fatty acid 
soap and may be based on actives other than fatty acid soap. Mildness 
improving salts, such as alkali metal salt or isethionate, are also 
typically added. In addition other ingredients, such as germicides, 
perfumes, colorants, pigments, suds-boosting salts and anti-mushing agents 
may also be added. 
Fatty acid soaps are typically alkali metal or alkanol ammonium salts of 
aliphatic alkane or alkene monocarboxylic acids. Sodium, potassium, mono-, 
di- and tri-ethanol ammonium cations, or combinations thereof, are 
suitable for purposes of the invention. 
The soaps are well known alkali metal salts of natural or synthetic 
aliphatic (alkanoic or alkenoic) acids having about 8 to 22 carbons, 
preferably 12 to about 18 carbons. 
Examples of soap which may be used may be found in U.S. Pat. No. 4,695,395 
to Caswell et al. and U.S. Pat. No. 4,260,507 (Barrett), both of which are 
incorporated herein by reference. 
In a soap-based bar, fatty acid soaps will generally comprise greater than 
25% of the composition, generally from 30-95%. Preferably, the amount of 
soap will range from 40% to 70% by weight of the composition. In a 
bar-based on other actives, soap may comprise 0-50% by weight. In general, 
C.sub.8 to C.sub.24 fatty acid comprises 5-60% of the composition. 
The compositions will also generally comprise a non-soap detergent which is 
generally chosen from anionic, nonionic, cationic, zwitterionic or 
amphoteric synthetic detergent materials or mixtures thereof. These 
surfactants are all well known in the art and are described, for example, 
in U.S. Pat. Nos. 4,695,395 and 4,260,507 discussed above. One preferred 
non-soap anionic is a C.sub.8 -C.sub.22 akyl isethionate. These ester may 
be prepared by the reaction between alkali metal isethionate and mixed 
aliphatic fatty acids having from 8 to 22 carbons. The non-soap actives 
may comprise from 0 to 50% of the composition. 
A certain amount of free fatty acids of 8 to 22 carbons are also desirably 
incorporated into soap compositions to act as superfatting agents or as 
skin feel and creaminess enhancers. If present, the free fatty acids 
comprise between 1 and 15% of the compositions. 
A preferred mildness improving salt which may be added to soap compositions 
is a simple unsubstituted sodium isethionate. This may be present as 0.1 
to 50% of the composition, preferably 0.5% to 25%, more preferably 2% to 
about 15% by weight. Other mildness co-actives which may be used include 
betain compounds or ether sulphates. These also may be present at 0.1 to 
50% of the composition, preferably 0.5% to 25%. 
The sulfate ester surfactant may comprise 0.01 to 45% by weight of the 
composition (as the monoester), preferably 25% to 40%, and 0.01% to 10% of 
the composition (as the diester), preferably 0.01% to 5%. 
Other optional ingredients which may be present in soap bar compositions 
are moisturizers such as glycerin, propylene glycol, sorbitol, 
polyethylene glycol, ethoxylated or methoxylated ether of methyl glucose 
etc; water-soluble polymers such as collagens, modified cellulases (such 
as Polymer JR.RTM.), guar gums and polyacrylates; sequestering agents such 
as citrate, and emollients such as silicones or mineral oil. Another 
useful set of ingredients are various cosurfactants and non-soap 
detergents. 
In a second embodiment of the invention, the glycerol frame surfactant with 
ether linkage of the invention may be present in a facial or body 
cleansing composition. Examples of such cleaning compositions are 
described, for example, in U.S. Pat. No. 4,812,253 to Small et al. and 
U.S. Pat. No. 4,526,710 to Fujisawa, both of which are hereby incorporated 
by reference. 
Typically, cleansing compositions will comprise a fatty acid soap together 
with a non-soap surfactant, preferably a mild synthetic surfactant. 
Cleaning compositions will also generally include a moisturizer or 
emollient and polymeric skin feel and mildness aids. The compositions may 
further optionally include thickener (e.g. magnesium aluminum silicate, 
carbopol), conditioners, water soluble polymers (e.g. carboxymethyl 
cellulose), dyes, hydrotropes brighteners, perfumes and germicides. 
The fatty acid soaps used are such as those described above in uses in 
toilet bar formulations. These soaps are typically alkali metal or alkanol 
ammonium salts of aliphatic or alkene monocarboxylic salts. Sodium, 
potassium, mono-, di- and triethanol ammonium cations, or combinations 
thereof are suitable. Preferred soaps are 8 to 24 carbon half acid salts 
of, for example, triethanolamine. 
Surfactants can be chosen from anionic, nonionic, cationic, zwitterionic or 
amphoteric materials or mixtures thereof such as are described in U.S. 
Pat. No. 4,695,395 mentioned above, or in U.S. Pat. No. 4,854,333 to Inman 
et al, hereby incorporated by reference. 
Moisturizers are included to provide skin conditioning benefits and improve 
mildness. This term is often used as synonymous with emollient and is then 
used to describe a material which imparts a smooth and soft feeling to 
skin surface. 
There are two ways of reducing water loss from the stratum corneum. One is 
to deposit on the surface of the skin an occlusive layer which reduces the 
rate of evaporation. The second method is to add nonocclusive hydgroscopic 
substances to the stratum corneum which will retain water, and make this 
water available to the stratum corneum to alter its physical properties 
and produce a cosmetically desirable effect. Nonocclusive moisturizers 
also function by improving the lubricity of the skin. 
Both occlusive and nonocclusive moisturizers can work in the present 
invention. Some examples of moisturizers are long chain fatty acids, 
liquid water-soluble polyols, glycerin, propylene glycol, sorbitol, 
polyethylene glycol, ethoxylated/propoxylated ethers of methyl glucose 
(e.g., methyl gluceth-20) and ethoxylated/-propoxylated ethers of lanolin 
alcohol (e.g., Solulan-75). 
Preferred moisturizers are coco and tallow fatty acids. Some other 
preferred moisturizers are the nonoclusive liquid water soluble polyols 
and the essential amino acid compounds found naturally in the skin. 
Other preferred nonocclusive moisturizers are compounds found to be 
naturally occurring in the stratum corneum of the skin, such as sodium 
pyrrolidone carboxylic acid, lactic acid, urea, L-proline, guanidine and 
pyrrolidone. Examples of other nonocclusive moisturizers include 
hexadecyl, myristyl, isodecyl or isopropyl esters of adipic, lactic, 
oleic, stearic, isostearic, myristic or linoleic acids, as well as many of 
their corresponding alcohol esters (sodium isostearoyl-2 lactylate, sodium 
capryl lactylate), hydrolyzed protein and other collagen-derived proteins, 
aloe vera gel and acetamide MEa. 
Some occlusive moisturizers include petrolatum, mineral oil, beeswax, 
silicones, lanolin and oil-soluble lanolin derivatives, saturated and 
unsaturated fatty alcohols such as behenyl alcohol, squalene and squalane, 
and various animal and vegetable oils such as almond oil, peanut oil, 
wheat germ oil, linseed oil, jojoba oil, oil of apricot pits, walnuts, 
palm nuts, pistachio nuts, sesame seeds, rapeseed, cade oil, corn oil, 
peach pit oil, poppyseed oil, pine oil, castor oil, soybean oil, avocado 
oil, safflower oil, coconut oil, hazelnut oil, olive oil, grape seed oil 
and sunflower seed oil. 
Other examples of both types of moisturizers are disclosed in 
"Emollients--a Critical Evaluation," by J. Mausner, Cosmetics & 
Toiletries, May 1981, incorporated herein by reference. 
The polymeric skin feel and mildness aids useful in the present invention 
are the cationic, anionic, amphoteric, and the nonionic polymers used in 
the cosmetic field. Reduced skin irritation benefits as measured by patch 
testing of cationic and nonionic types of polymers are set out in "Polymer 
JR for Skin Care" Bulletin, by Union Carbide, 1977. The cationics are 
preferred over the others because they provide better skin feel benefits. 
The amount of polymeric skin feel and mildness aids found useful in the 
composition of the present invention is from about 0.01% to about 5%, 
preferably from about 0.3% to about 4%. In bar compositions with less than 
5.5% soap, the polymer is used at a level of 2% to 5%, preferably 3% or 
more. 
Other types of high molecular weight polymeric skin feel and skin mildness 
aids, such as nonionic guar gums, Merquats 100 and 550, made by Merck & 
Co, Inc.; Jaguar C-14-S made by Stein Hall; Mirapol a15 made by Miranol 
Chemical Company, Inc.; and Galactasol 811, made by Henkel, Inc.; plus 
others, are usable. The polymer also provides enhanced creamy lather 
benefits. 
The nonionic polymers found to be useful include the nonionic 
polysaccharides, e.g., nonionic hydroxypropyl guar gums, offered by 
Celanese Corp. A preferred nonionic hydroxypropyl guar gum material is 
Jaguar.RTM. HP-60 having molar substitution of about 0.6. Another class of 
useful nonionics is the cellulosic nonionic polymers, e.g., HEC and CMC. 
The cationic polymers employed in this invention also provide a desirable 
silky, soft, smooth in-use feeling. The preferred level for this invention 
is 0.1-5% of the composition. There is reason to believe that the 
positively charged cationic polymers can bind with negatively charges 
sites on the skin to provide a soft skin feel after use. Not to be bound 
by any theory, it is believed that the greater the charge density of the 
cationic polymer, the more effective it is for skin feel benefits. 
Other suitable cationic polymers are copolymers of 
dimethylaminoethylmethacrylate and acrylamide and copolymers of 
dimethyldiallylammonium chloride and acrylamide in which the ratio of the 
cationic to neutral monomer units has been selected to give a copolymer 
having a cationic charge. Yet other suitable types of cationic polymers 
are the cationic starches, e.g., Sta-Lok.RTM.300 and 400 made by Staley, 
Inc. 
A more complete list of cationic polymers useful in the present invention 
is described in U.S. Pat. No. 4,438,095, to Grollier/allec, issued Mar. 
20, 1984, incorporated herein by reference. Some of the more preferred 
cationics are listed in Col. 3, Section 2; Col. 5, section 8; Col. 8, 
section 10; and Col. 9, lines 10-15 of the Grollier/allec patent, 
incorporated herein by reference. 
In a third embodiment of the invention, the surfactant of the invention may 
be used, for example, in a shampoo. Examples of such compositions are 
described in U.S. Pat. No. 4,854,333, to Inman and U.S. Pat. No. 4,526,710 
to Fujisawa, both of which are hereby incorporated by reference. 
The shampoo compositions which may be used typically comprise a surfactant 
selected from any one of a wide variety of surfactants known in the art 
(such as those described in U.S. Pat. No. 4,854,333, incorporated herein 
by reference). 
Synthetic anionic surfactants, for example can be exemplified by the alkali 
metal salts of organic sulfuric reaction products having in their 
molecular structure an alkyl radical containing from about 8-22 carbon 
atoms and a sulfonic acid or sulfuric acid ester radical (included in the 
term alkyl is the alkyl portion of higher acyl radicals). Preferred are 
the sodium, ammonium, potassium or triethanolamine alkyl sulfates, 
especially those obtained by sulfating the higher alcohols (C8-C18 carbon 
atoms), sodium coconut oil fatty acid monoglyceride sulfates and 
sulfonates; sodium or potassium salts of sulfuric acid esters of the 
reaction product of about 1 mole of a higher fatty alcohol (e.g., tallow 
or coconut oil alcohols) and from about 1 to about 12 moles of ethylene 
oxide; sodium or potassium salts of alkyl phenol ethylene oxide ether 
sulfate with from about 1 to about 10 units of ethylene oxide per molecule 
and in which the alkyl radicals contain from about 8 to about 12 carbon 
atoms; sodium alkyl glyceryl ether sulfonates; the reaction product of 
fatty acids having from 10 to about 22 carbon atoms esterified with 
isethionic acid and neutralized with sodium hydroxide; and water soluble 
salts of condensation products of fatty acids with sarcosine. 
Examples of amphoteric surfactants which can be used in the compositions of 
the present invention are those broadly described as derivatives of 
aliphatic secondary and tertiary amines in which the aliphatic radical can 
be straight chain or branched and wherein one of the aliphatic 
substituents contains from about 8 to about 18 carbon atoms and one 
contains an anionic water solubilizing group, e.g., carboxy, sulfonate, 
sulfate, phosphate, or phosphonate. Examples of compounds falling within 
this definition are sodium 3-dodecyl-aminopropionate; sodium 
3-dodecylaminopropane sulfonate; N-alkyltaurines, such as the one prepared 
by reacting dodecylamine with sodium isethionate according to the teaching 
of U.S. Pat. No. 2,658,072; N-higher alkyl aspartic acids, such as those 
produced according to the teaching of U.S. Pat. No. 2,438,091; and the 
products sold under the trade name "Miranol" and described in U.S. Patent 
No. 2,528,378. The shampoo compositions may additionally comprise a 
compound considered useful for treating dandruff, e.g. selenium sulfide. 
The compositions all may also optionally comprise a suspending agent, for 
example, any of several acyl derivative materials or mixtures thereof. 
Among these are ethylene glycol esters of fatty acids having 16 to 22 
carbons. Preferred suspending agents include ethylene glycol stearates, 
both mono- and distearate. Preferred alkanol amides are stearic 
monoethanolamide, stearic diethanolamide and stearic monoisopropanolamide. 
Still other long chain acyl derivatives include long chain esters of long 
chain fatty acids (e.g., stearyl stearate, cetyl palmitate), glyceryl 
esters (e.g. glyceryl distearate), and long chain esters of long chain 
alkanol amides (e.g., stearamide DEA distearate, stearamide MEA stearate). 
Still other suitable suspending agents are alkyl (16 to 22 carbon) dimethyl 
amine oxides, such as stearyl dimethyl amine oxide. If the compositions 
contain an amine oxide or a long chain acyl derivative as a surfactant, 
these components may also provide the suspending function and additional 
suspending agent may not be needed. 
Xanthan gum is another agent used to suspend, for example, selenium sulfide 
which may be in the present compositions. This biosynthetic gum material 
is commercially available and is a heteropolysaccharide with a molecular 
weight of greater than 1 million. It is believed to contain D-glucose, 
D-mannose and D-glucuronate in the molar ratio of 2.8:2.0:2.0. The 
polysaccharide is partially acetylated with 4.7% acetyl. Supplemental 
information on these agents is found in Whistler, Roy L. (Editor), 
Industrial Gums--Polysaccharides and Their Derivatives New York: Academic 
Press, 1973. Kelco, a Division of Merck & Co., Inc., offers xanthan gum as 
Keltrol.RTM.. 
A particularly preferred suspending system comprises a mixture of xanthan 
gum, present at a level of from about 0.05% to about 1.0%, preferably from 
about 0.2% to about 0.4%, of the compositions, together with magnesium 
aluminum silicate (Al.sub.2 Mg.sub.8 Si.sub.2), present at a level of from 
about 0.1% to about 3.0%, preferably from about 0.5% to about 2.0%, of the 
compositions. Magnesium aluminum silicate occurs naturally in such 
smectite minerals as colerainite, saponite and sapphire. Refined magnesium 
aluminum silicates useful herein are readily available, for example as 
veegum, manufactured by R. T. Vanderbilt Company, Inc. Mixtures of 
suspending agents are also suitable for use in the compositions of this 
invention. 
Other useful thickening agents are the cross-linked polyacrylates such as 
those manufactured by B. F. Goodrich and sold under the Carbopol.RTM. 
tradename. 
Another optional component for use in the present compositions is an amide. 
The amide used in the present compositions can be any of the alkanolamides 
of fatty acids known for use in shampoos. These are generally mono- and 
diethanolamides of fatty acids having from about 8 to 24 carbon atoms. 
Preferred are coconut monoethanolamide, lauric diethanolamide and mixtures 
thereof. The amide is present at a level of from about 1% to about 10% of 
the compositions. 
The compositions may also contain nonionic polymer material which is used 
at a low level to aid in dispersing particles. The material can be any of 
a large variety of types including cellulosic materials such as 
hydroxypropyl methyl cellulose, carboxymethyl cellulose, hydroxyethyl 
cellulose and sodium carboxymethyl cellulose as well as mixtures of these 
materials. 
Other materials include alginates, polyacrylic acids, polyethylene glycol 
and starches, among many others. The nonionic polymers are discussed in 
detail in Industrial Gums, edited by Roy L. Whistler, academic Press, 
Inc., 1973, and Handbook of Water-Soluble Gums and Resins, edited by 
Robert L. Davidson, McGraw-Hill, Inc., 1980. Both of these books in their 
entirety are incorporated herein by reference. 
When included, the nonionic polymer is used at a level of from about 0.001% 
to about 0.1%, preferably from about 0.002% to about 0.05%, of the 
composition. Hydroxypropyl methyl cellulose is the preferred polymer. 
Another suitable optional component useful in the present compositions is a 
nonvolatile silicone fluid. 
The nonvolatile silicone fluid may be either a polyalkyl siloxane, a 
polyaryl siloxane, a polyalkylarly siloxane or a polyether siloxane 
copolymer and is present at a level of from about 0.1% to about 10.0%, 
preferably from about 0.5% to about 5.0%. Mixtures of these fluids may 
also be used and are preferred in certain executions. The dispersed 
silicone particles should also be insoluble in the shampoo matrix. This is 
the meaning of "insoluble" as used herein. 
The essentially nonvolatile polyalkyl siloxane fluids that may be used 
include, for example, polydimethyl siloxanes with viscosities ranging from 
about 5 to about 600,000 centistokes at 25.degree. C. These siloxanes are 
available, for example, from the General Electric Company as the Viscasil 
series and from Dow Corning as the Dow Corning 200 series. The siloxane 
viscosity can be measured by means of a glass capillary viscometer as set 
forth in Dow Corning Corporate Test Method CTM0004, Jul. 20, 1970. 
Preferably the viscosity of the these siloxanes range from about 350 
centistokes to about 100,000 centistokes. 
The essentially nonvolatile polyether siloxane copolymer that may be used 
is, for example, a polypropylene oxide modified dimethylpolysiloxane 
(e.g., Dow Corning DC-1248), although ethylene oxide or mixtures of 
ethylene oxide and propylene oxide may also be used. 
Suitable silicone fluids are described in U.S. Pat. No. 2,826,551, Geen; 
U.S. Pat. No. 3,946,500, Jun. 22, 1976, Drakoff; U.S. Pat. No. 4,364,837, 
Pader; and British Patent 849,433, Woolston. All of these patents are 
incorporated herein by reference. Also incorporated herein by reference is 
Silicon compounds, distributed by Petrarch Systems, Inc., 1984. This 
reference provides a very good listing of suitable silicone materials. 
Another silicone material useful is silicone gum. Silicone gums are 
described by Petrarch and others including U.S. Pat. No. 4,152,416, May 1, 
1979, Spitzer, et al., and Noll, Chemistry and Technology of Silicones, 
New York, academic Press, 1968. Useful silicone gums are also described in 
General Electric Silicone Rubber Product Data Sheets SE 30, SE 33, SE 54 
and SE 76. all of these references are incorporated herein by reference. 
"Silicone gum" materials denote high molecular weight 
polydiorganosiloxanes having a mass molecular weight of from about 200,000 
to about 1,000,000. Specific examples include polydimethylsiloxane, 
(polydimethylsiloxane) (methylvinylsiloxane) copolymer, 
poly(dimethylsiloxane) (diphenyl) (methylvinylsiloxane) copolymer, and 
mixtures thereof. Mixtures of silicone fluids and silicone gums are also 
useful herein. 
The shampoos herein can contain a variety of other nonessential optional 
components suitable for rendering such compositions more formulatable, or 
aesthetically and/or cosmetically acceptable. Such conventional optional 
ingredients are well-known to those skilled in the art and include, e.g., 
preservatives, such as benzyl alcohol, methyl paraben, propyl paraben, and 
imidazolinidyl urea; cationic surfactants, such as cetyl trimethyl 
ammonium chloride, lauryl trimethyl ammonium chloride, tricetyl methyl 
ammonium chloride, stearyldimethyl benzyl ammonium chloride, and 
di(partially hydrogenated tallow) dimethylammonium chloride; menthol; 
thickeners and viscosity modifiers, such as block polymers of ethylene 
oxide and propylene oxide such as Pluronic F88 offered by BaSa Wyandotte, 
sodium chloride, sodium sulfate, propylene glycol, and ethyl alcohol; pH 
adjusting agents, such as citric acid, succinic acid, phosphoric acid, 
sodium hydroxide, sodium carbonate; perfumes; dyes; and sequestering 
agents, such as disodium ethylenediamine tetraacetate. Such agents 
generally are used individually at a level of from about 0.01% to about 
10%, preferably from about 0.5% to about 5.0%, of the composition. 
A typical shampoo composition may comprise (percentages by weight): 
(1) 5-15% active of invention 
(2) 0-10% anionic coactive; 
(3) 0-10% amphoteric coactive; 
(4) 0-5% lauramide MEA; 
(5) 0-5% thickener; 
(6) 0-2% fragrance; 
(7) 0-1% preservative; and 
(8) remainer water. 
In a fourth embodiment of the invention, the surfactant of the invention 
may be used in a conditioner composition such as is taught and described 
in U.S. Pat. No. 4,913,828 to Caswell et al. which is hereby incorporated 
by reference. 
More particularly, conditioner compositions are those containing a 
conditioning agent (e.g. alkylamine compounds) such as those described in 
U.S. Pat. No. 4,913,828. 
A typical conditioner composition may comprise (percentages by weight): 
(a) 1-98% surfactant of invention, preferably 10-60% (or 1-98% or 10-60% 
surfactant mixture comprising the surfactant of the invention and wherein 
cosurfactant(s) are selected from the group consisting of anionics, 
nonionics, ampholytics, zwitterionics and cationics); 
(b) 0-80% builder (e.g. , polycarboxylates); 
(c) 0-10% chelating agent (e.g., amino carboxylates); 
(d) 0-5% soil release agent (e.g., derivative of hydro)of ether cellulosic 
polymers); 
(e) 0-5% antiredeposition agent (e.g., ethoxylated anionics); 
(f) 0-2% enzymes (e.g. , protease); 
(g) 0.1-20% conditioning agent (e.g., cationic surfactant); 
(h) 0.1-10% stabilizer for conditioner (e.g., clay or polysaccharide gum); 
(i) water and minors to 100%. 
If formulated as conditioner shampoos, the composition may comprise: 
(a) 5-60% surfactant (wholly surfactant of invention or comprising the 
surfactant of invention); 
(b) 1-60% conditioner; 
(c) 0-20% preservative (e.g. , benzyl alcohol); 
(d) 0-16% thickener (e.g., diethanolamide); and 
(e) remainder water and minors. 
In a fifth embodiment of the invention, the surfactant may be used in a 
cosmetic composition, such as is taught and is described in EP 0,371,803. 
Such compositions generally comprise thickening agents, preservatives and 
further additions. 
The composition may comprise polymer thickener in an amount sufficient to 
adjust the viscosity of the composition, so as to facilitate dispensing it 
conveniently onto the body surface. 
Examples of polymer thickeners include: anionic cellulose materials, such 
as sodium carboxy methyl cellulose; anionic polymers such as carboxy vinyl 
polymers, for example, Carbomer 940 and 941; nonionic cellulose materials, 
such as methyl cellulose and hydroxy propyl methyl cellulose; cationic 
cellulose materials, such as Polymer JR 400; cationic gum materials, such 
as Jaguar C13 S; other gum materials such as gum acacia, gum tragacanth, 
locust bean gum, guar gum and carrageenan; proteins, such as albumin and 
protein hydrolysates; and clay materials, such as bentonite, hectorite, 
magnesium aluminum silicate, or sodium magnesium silicate. 
Generally, the thickening agent may comprise from 0.05 to 5%, preferably 
0.1 to 1% by weight of the composition. 
The composition according to the invention can also optionally comprise a 
preservative to prevent microbial spoilage. 
Examples of preservatives include: 
(i) Chemical preservatives, such as ethanol, benzoic acid, sodium benzoate, 
sorbic acid, potassium sorbate, sodium propionate and the methyl, ethyl, 
propyl and butyl esters of p-hydroxybenzoic acid 2-bromo-2-nitropropane-1, 
3-diol, phenoxyethanol, dibromodicyanobutane, formalin and Tricolsan. The 
amount of chemical preservative optionally to be incorporated in the 
composition according to the invention will generally be from 0.05 to 5%, 
preferably from 0.01 to 2% by weight, the amount chosen being sufficient 
to arrest microbial proliferation. 
(ii) Water activity depressants, such as glycerol, propylene glycol, 
sorbitol, sugars and salts, for examples alkali metal halides, sulphates 
and carboxylates. When employing a water activity depressant, sufficient 
should be incorporated in the composition according to the invention to 
reduce the water activity from 1 to &lt;0.9, preferably to &lt;0.85 and most 
preferably&lt;0.8, the lowest of these values being that at which yeasts, 
molds and fungi will not proliferate. 
The composition can also contain other optional adjuncts, which are 
conventionally employed in compositions for topical application to human 
skin. These adjuncts, when present, will normally form the balance of the 
composition. 
Examples of optional adjuncts include vehicles, the selection of which will 
depend on the required product form of the composition. Typically, the 
vehicle when present, will be chosen from diluents, dispersants or 
carriers for the dialkyl or dialkenyl phosphate salt so as to ensure an 
even distribution of it when applied to the skin. 
Compositions according to this invention can include water as a vehicle, 
usually with at least one other cosmetically-acceptable vehicle. 
Vehicles other than water that can be used in compositions according to the 
invention can include liquids or solids as emollients, solvents, 
humectants, thickeners and powders. Examples of each of these types of 
vehicles, which can be used singly or as mixtures of one or more vehicles, 
are as follows: 
Emollients, such as stearyl alcohol, glyceryl monolaurate, glyceryl 
monoricinoleate, glyceryl monostearate, propane-1, 2-diol, butane-1.3 
diol, docosan-1,2-diol, mink oil, cetyl alcohol, isopropyl isostearate, 
stearic acid, isobutyl palmitate, isocetyl stearate, oleyl alcohol, 
isopropyl laurate, hexyl laurate, decyl oleate, octadecan-2-ol, isocetyl 
alcohol, eicosanyl alcohol, behenyl alcohol, cetyl palmitate, silicone 
oils such as dimethylpolysiloxane, di-n-butyl sebacate, isopropyl 
myristate, isopropyl palmitate, isopropyl stearate, butyl stearate, 
polyethylene glycol, triethylene glycol, lanolin, cocoa butter, corn oil, 
cotton seed oil, tallow, lard, olive oil, palm kernel oil, rapeseed oil, 
safflower seed oil, soybean oil, sunflower seed oil, olive oil, sesame 
seed oil, coconut oil, arachis oil, castor oil, acetylated lanolin 
alcohols, petroleum, mineral oil, butyl myristate, isostearic acid, 
palmitic acid isopropyl linoleate, lauryl lactate, myristyl lactate, decyl 
oleate, myristyl myristate; 
Propellants, such as trichlorofluoromethane, dichlorodifluoromethane, 
dichlorotetrafluoromethane, monochlorodifluoromethane, 
trichlorotrifluoromethane, propane, butane, isobutane, dimethyl ether, 
carbon dioxide, nitrous oxide; 
Solvents, such as ethyl alcohol, methylene chloride, isopropanol, acetone, 
castor oil, ethylene glycol monoethyl ether, diethylene glycol monobutyl 
ether, diethylene glycol monoethyl ether, dimethyl sulphoxide, dimethyl 
formamide, tetrahydrofuran; 
Humectants, such as glycerin, sorbitol, sodium 2-pyrrolidone-5-carboxylate, 
soluble collagen, dibutyl phthalate, gelatin; 
Powders, such as chalk, talc, fullers earth, kaolin, starch, gums, 
colloidal silicon dioxide, sodium polyacrylate, tetra alkyl and/or 
trialkyl aryl ammonium smectites, chemically modified magnesium aluminum 
silicate, organically modified montmorillonite clay, hydrated aluminum 
silicate, fumed silica, carboxyvinyl polymer, sodium carboxymethyl 
cellulose, ethylene glycol monostearate. 
The cosmetically acceptable vehicle, when present, will usually form from 
0.01 to 99.9%, preferably from 59 to 98% by weight of the composition, and 
can, in the absence of other cosmetic adjuncts, form the balance of the 
composition. 
A wide variety of conventional sunscreening agents, such as those described 
in U.S. Pat. No. 4,919,934 to Deckner et al. hereby incorporated by 
reference, may also be used in the cosmetic compositions of the invention. 
Such agents include, for example, p-aminobenzoic acid, its salts and its 
derivatives, anthranilates, salicylates, cinnamic acid derivatives, di- 
and trihydroxy cinnamic acid derivatives, hydrocarbons such as 
diphenylbutadiene and stilbene, dibenzalacetone and benzalacetophenone, 
naphthasulfonates, di-hydroxy naphthloic acid and its salts, hydroxy 
diphenylsulfonates, coumarin derivatives, diazoles, quinine salts, 
quinoline derivatives, hydroxy or methoxy substituted benzophenones, uric 
or vilouric acid, tannic acid and its derivatives, hydroquinone, and 
benzophenones. 
In a sixth embodiment of the invention, the surfactant may be used in a 
toothpaste composition such as is taught and is described in U.S. Pat. No. 
4,935,227 to Duckworth, which is hereby incorporated by reference. 
Such compositions generally comprise abrasive gels (e.g. calcium 
carbonate), oral therapeutic agents (e.g., flourine containing compound), 
coactives, flavoring agents, sweetening agents, humectants and binding or 
thickening gels. 
Preferred toothpastes of this invention comprise 0 to 1.5% by weight of 
anionic surfactant. In more preferred products the amount of anionic 
surfactant is 0 to 1% by weight with most preferred amounts being 0 to 
0.75% by weight. 
Toothpastes of this invention may include other surfactants, especially 
non-ionic surfactants. 
Toothpaste of the invention will also comprise the usual additional 
ingredients in particular humectant binder or thickening agent. 
Humectants which may be used include glycerol, sorbitol syrup, polyethylene 
glycol, lactitol, xylitol or hydrogenated corn syrup. The total amount of 
humectant present will generally range from 10% to 85% by weight of the 
toothpaste. 
Numerous binding or thickening agents have been indicated for use in 
toothpastes, preferred ones being sodium carboxymethylcellulose, 
cross-linked polyacrylates and xanthan gum. Others include natural gum 
binders such as gum tragacanth, gum karaya and gum arabic, Irish moss, 
alginates, and carrageenans. Silica thickening agents include the silica 
aerogels and various precipitated silicas. Mixtures of binders and 
thickeners may be used. The amount of binder and thickening agent included 
in a toothpaste is generally between 0.1 and 15% by weight. 
A typical toothpaste composition may comprise (percentages by weight): 
______________________________________ 
Ingredients % by Weight 
______________________________________ 
Synthetic surfactants (sodium 
.01-3% 
lauryl sulfate) 
Surfactant of Invention 
1-10% 
Alkyl or aryl sulfate or 
0-1% 
sulfonate 
Abrasive (e.g., silic acid/ 
20-55% 
CaCO.sub.3) 
Active ingredients (e.g., 
0.1-2% 
Pyrophosphates) 
Humectant (glycerin, sorbitol) 
10-45% 
Thickeners (cellulose 
0-3% 
derivatives) 
Sequestering agents (e.g. 
0.1-0.4% 
citrate) 
Flavoring agents 0.5-2% 
Sweeteners 0-0.5% 
Dye stuff 0-0.1% 
Water Balance 
______________________________________ 
In a seventh embodiment of the invention, the molecule of the invention may 
be used in a light duty liquid detergent composition such as those taught 
in U.S. Pat. No. 4,671,894 to Lamb et al. U.S. Pat. No. 4,368,146 to 
Aronson et al. and U.S. Pat. No. 4,555,366 to Bissett et al., all of which 
are hereby incorporated by reference into the subject application. 
Generally such compositions comprise a mixture of sulphate and sulphonate 
anionic surfactants together with a suds stabilizing agent. These 
compositions may also comprise nonionic surfactants designed to reduce the 
level of non-performing ingredients such as solvents and hydrotropes and 
zwitterionic surfactants for providing enhanced grease and particulate 
soil removal performance. 
Among other ingredients which may also be used in such compositions are 
opacifiers (e.g. ethylene glycol distearate), thickeners (e.g., guar gum), 
antibacterial agents, antitarnish agents, heavy metal chelators (e.g. 
ETDA), perfumes and dyes. 
A typical light duty liquid composition maly comprise (all percentages by 
weight): 
(a) 0.01-65% anionic; 
(b) b 0.01-50% surfactant of invention; 
(c) 0-8% suds producing agent (e.g. alkyl alcohol amide); 
(d) 0-10% hydrotrope (e.g., benzene sulfonate); and 
(e) minors plus water to 100%. 
In an eighth embodiment of the invention the molecule of the invention may 
be used in underarm deodorant/antiperspirant compositions such as those 
taught in U.S. Pat. No. 4,919,934 to Deckner, U.S. Pat. No. 4,944,937 to 
McCall and U.S. Pat. No. 4,944,938 to Patini, all of which patents are 
hereby incorporated by reference. 
Such compositions generally comprise a cosmetic stick (gel or wax) 
composition which in turn generally comprises one or more liquid base 
materials (e.g., water, fatty acid and fatty alcohol esters, 
water-insoluble ethers and alcohols, polyorganosiloxanes); a solidifying 
agent for solidifying the liquid base; and an active component such as 
bacteriostats or fungistats (for anti-deodorant activity) or astringent 
metallic salts (for antiperspirant activity). 
These compositions may also comprise hardeners, strenghteners, emollients, 
colorants, perfumes, emulsifiers and fillers. 
While various compositions are described above, these should not be 
understood to be limiting as to what other personal product compositions 
may be used since other compositions which may be known to those of 
ordinary skill in the art are also contemplated by this invention. 
The invention is set forth in greater detail in the examples which follow 
below. These examples are merely to illustrate the invention and are not 
intended to be limiting in any way. 
EXAMPLE 1 
Synthesis of 3 -(octyloxy)-2-hydroxypropyl-.beta.-D-galactopyranoside 
Acetobromogalactose (2,3,4,6-tetra-O-acetyl-.alpha.-D-galactopyranosyl 
bromide) was mixed with allyl alcohol and mercuric cyanide via the 
Koenigs-Knorr glycosylation to obtain ally-.beta.-D-galactopyranoside 
tetraacetate. This was followed by oxidation with 3-chloroperoxybenzoic 
acid in dichloromethane to obtain 
2,3-epoxypropyl-.beta.-D-galactopyranoside 2,3,4,6-0-tetraacetate (epoxide 
compound). To a solution of the above-identified epoxide compound (0.50 g, 
1.24 mmoles) and 1-octanol (5-6 ml) was added 0.045 g of DDQ 
(2,3-dichloro-5,6-dicyano-1,4-benzoquinone). The reaction was run at 
60.degree.-70.degree. C. under an inert atmosphere of nitrogen. Reaction 
was followed by thin layer chromatography in an eluent of 50/50 volume of 
ethyl acetate/hexane. The product had a Rf value of 0.6. After one day 
another 0.06 g of DDQ was added to the mixture. When the reaction was 
complete, the product (0.35 g) was isolated by column chromatography on 60 
A (Merck) silica gel in a solvent system consisting of 50% ethyl 
acetate/50% hexane. 
Deprotection was done using sodium methoxide in 35 ml of anhydrous methanol 
for 5-6 hours. Methanol was removed under reduced pressure. This crude 
product was further purified on a silica gel column (9:1 CHCl3, MeOH) to 
give the final product as a white solid (0.15 g) as seen below: 
##STR6## 
EXAMPLE 2 
Synthesis of 3-dodecyloxy)-2-hydroxypropyl-.beta.-D-galactopyranoside 
The epoxide was obtained as described in Example 1. To a solution of the 
epoxide (1.20 g, 2.97 mmoles) and n-dodecanol (12 ml) was added 0.55 g of 
DDQ. The temperature was raised to 80.degree.-85.degree. C. and the 
reaction was monitored by TLC. After 3 days the starting epoxide was 
completely reacted. 
The product was isolated by column chromatography on 60A (Merk) silica gel 
using a solvent system consisting of 50/50 v/v Hexane:ethyl acetate. The 
product had a Rf value of 0.65 and 1.06 g of a light caramel colored syrup 
was isolated (61% yield). 
Deprotection was accomplished as in Example 1. The above product was 
dissolved in 50 ml of anhydrous methanol with a catalytic amount of sodium 
methoxide. The reaction was allowed to stir for 5-6 hours and subsequently 
treated with Bio-Rad cation exchange resin (AG 50W-X8 50-100 mesh). The 
resin was filtered off and methanol was removed under reduced pressure to 
afford a tacky solid. Addition of ether to the tacky solid gave a white 
precipitate (0.69 g, 91% yield). 
EXAMPLE 3 
Synthesis of 3-(hexadecyloxy)-2-hydroxypropyl-.beta.-D-galactopyranoside 
The epoxide was obtained as described in Example 1. The epoxide was reacted 
with 10 equivalents of hexadecanol and catalytic amounts of DDQ at 
90.degree.-100.degree. C. under same conditions as for the dodecyl chain. 
Deacetylation and purification (same as Example 2) gave the final product 
EXAMPLE 4 
Alternative Syntheses of 
3-(octyloxy)-2-hydroxypropyl-.beta.-D-galactopyranoside 
In a 25 ml two neck round bottom flask was added 0.80 q (1.98 mmoles) of 
2,3-epoxypropyl-.beta.-D-galactopyranoside 2,3,4,6-0-tetraacetate and 4.0 
equivalents of 1-octanol. The reaction mixture was cooled to -10.degree. 
C. followed by addition of 0.034 equivalent of a 1.0M solution of 
SnCl.sub.4 in dichloromethane. The reaction was allowed to warm up to room 
temperature over a period of one hour, and then heated to a temperature of 
45.degree. C. for 12-14 hours. Column chromatography was used to purify 
the product. The excess octanol was initially isolated using a 9:1 
hexane/ethyl acetate eluent. Subsequent elution with 1:1 hexane/ethyl 
acetate gave 0.55 g of a clear syrupy material (52% yield). .sup.1 H NMR 
and MS showed identical spectra to the DDQ reaction product. Deprotection 
(same as Example 1) gave 0.36 g (95% yield) of final product. 
SURFACTANCY 
In order to determine the effectiveness of these compounds as surfactant, 
various physical properties (i.e., CMC, Krafft point, foam height, 
detergency) are tested relative to other known surfactants. These results 
are discussed in Examples 5 to 9 below. 
EXAMPLE 5 
Critical Micelle Concentration (CMC) 
The CMC is defined as the concentration of a surfactant at which it begins 
to form micelles in solution. Specifically, materials that contain both a 
hydrophobic group and a hydrophilic group (such as surfactants) will tend 
to distort the structure of the solvent (i.e., water) they are in and 
therefore increase the free energy of the system. They therefore 
concentrate at the surface, where, by orienting so that their hydrophobic 
groups are directed away from the solvent, the free energy of the solution 
is minimized. Another means of minimizing the free energy can be achieved 
by the aggregation of these surface-active molecules into clusters or 
micelles with their hydrophobic groups directed toward the interior of the 
cluster and their hydrophilic groups directed toward the solvent. 
The value of the CMC is determined by surface tension measurements using 
the Wilhemy plate method or Du Nuey ring method. While not wishing to be 
bound by theory, it is believed that a low CMC is a measure of surface 
activity (i.e., lower CMC of one surfactant versus another indicates the 
surfactant with lower CMC is more surface active). In this regard, it is 
believed that lower CMC signifies that lesser amounts of a surfactant are 
required to provide the same surfactancy benefits as a surfactant with 
higher CMC. 
The CMC of 3-(dodecyloxy)-2-hydroxypropyl-.beta.-D-galactopyranoside was 
measured at 1.23.times.10.sup.-4 M at 25.degree. C. The CMC of n-C.sub.12 
alcohol with 7 ethoxylated units (from Neodol.TM. surfactants ex Shell) is 
7.3.times.10.sup.-5 M [40.degree. C.]. This indicates that the surfactants 
of the invention are comparable to other well-known commercially available 
surfactants. 
EXAMPLE 6 
Krafft Points 
The temperature at and above which surfactants begin to form micelles is 
referred to as Krafft point (Tk) and at this temperature the solubility of 
a surfactant becomes equal to its CMC. 
Krafft point was measured by preparing a 1% dispersion of the surfactant in 
water. If the surfactant was soluble at room temperature, the solution was 
cooled to 0.degree. C. When the surfactant did not precipitate out, its 
Krafft point was considered to be &lt;0.degree. C. If it precipitated out, 
the solution was slowly warmed with stirring in a water bath. The 
temperature at which the precipitate dissolved was determined to be the 
Krafft point. 
If the Krafft point was above room temperature, the solution was first 
heated rapidly to dissolve all the surfactant. It was then cooled until 
precipitation occurred, and was then slowly warmed to determine the Krafft 
point described above. 
While not wishing to be bound by theory, it is believed that lower Krafft 
points are indicative of a surfactant being more soluble in aqueous 
system. Also, since micelles exist only at temperature above Tk, 
surfactants with high Tk will show lower activity at low temperatures. 
Finally, it is believed that surfactants with lower Krafft points are 
easier to formulate in multi-electrolyte systems because of their greater 
tolerance to salt. 
The Krafft point of 
3-(dodecyloxy)-2-hydroxypropyl-.beta.-D-galactopyranoside has been 
measured at about less than 8.degree. C. This Krafft point is another good 
indication of surfactant activity. 
EXAMPLE 7 
Foam Height 
Foam is an important attribute in many consumer products. Foam is one of 
the dominant factors that determines the commercial value of products such 
as shampoo, soap, etc. Also, acceptability of many consumer products is 
closely related to the quality and texture of the foam they produce 
(psychological aspect). 
Since most of the foaming data on surfactants is typically obtained by the 
Ross-Miles method (Ross, J. and Miles, G. D., Am. Soc. for Testing 
Material Method D1173-53 Philadelphia, PA. [1953]; Oil & Soap 
[1958]62:1260) the foaming ability of these surfactants was also acquired 
using this method. 
In the Ross-Miles method, 200 mL of a solution of surfactant contained in a 
pipette of specified dimensions with a 2.9-mm-i.d. orifice is allowed to 
fall 90 cm onto 50 mL of the same solution contained in a cylindrical 
vessel maintained at a given temperature by means of a water jacket. The 
height of the foam produced in the cylindrical vessel is read immediately 
after all the solution has run out of the pipette (initial foam height) 
and then again after a given amount of time. 
Using this method, the foam production (measured initially) and foam 
stability (the height after 10 minutes) are reported. All of the foaming 
was achieved at 45.degree. C. in water with 120 ppm hardness. The foam 
height is represented in millimeters (mm). 
The initial foam height and height after 10 minutes (i.e. foam stability) 
was measured for 
3-(dodecyloxyl)-2-hydroxypropyl-.beta.-D-galactopyranoside (DHG) and for a 
common surfactant, sodium dodecyl sulfonate (SDS) and results set forth 
below: 
______________________________________ 
Initial Height 
After 10 Minutes 
______________________________________ 
DHG 135 124 
SDS 153 144 
______________________________________ 
As seen from this data, the foaming ability of DHG is comparable to that of 
other well-known, commercially available surfactants. 
EXAMPLE 8 
The detergency of the surfactants of the invention was measured by 
recording the % triolein (a grease substance) removed (as an absolute 
value) from polyester using 
3-(dodecyloxy)-2-hydroxypropyl-.beta.-D-galactopyranoside (DHG) alone or 
in combination with a C.sub.12 nonionic surfactant with three alkoxylated 
groups. 
More particularly, the amount of soil removed was evaluated using .sup.3 H 
ratio-labelled triolein. Following the wash, 4.times.1 ml samples of wash 
liquor were removed from each pot and the activity determined using a 
liquid scintillation counter. Percentage detergencies were calculated from 
the relationship. 
##EQU1## 
Aw=total activity in wash liquor As=level of activity originally applied 
to cloth 
Using these methods, the following results were obtained: 
______________________________________ 
% Detergency Based on Various 
Ratios of DHG to C.sub.12 E.sub.3 * 
100% 100% 
DHG 80/20 60/40 40/60 20/80 C.sub.12 E.sub.3 
______________________________________ 
Detergency 
55% 57% 72% 50% 10% 2% 
______________________________________ 
*Temperature 40.degree. C., pH 10.7, Dose 1 g/l.sup.-1, 0.05M (NaBO.sub.2 
4H.sub.2 O) 
First, it should be noted that anything above 45% detergency is considered 
adequate detergency. From this, it can be seen that use of DHG alone (55% 
detergency) provides very good surfactancy on grease staining. 
In addition, it can be seen that, when DHG is used in combination with 
cosurfactant, optimum benefits are obtained at a range of about 20-60% 
cosurfactant. At levels beyond about 65% cosurfactant, the detergency 
effect of the DHG is minimized. 
While not wishing to be bound by theory, it should also be noted that, 
since the surfactants used in the composition of the invention have 
relatively high hydrophilic-lipophilic balance, in formulating detergent 
composition, optimal synergistic detergency affects with cosurfactants 
should occur when using cosurfactants having a lower 
hydrophilic-lipophilic balance. 
EXAMPLE 9 
In Example 8, applicants tested detergency by combining the compounds of 
the invention with low alkoxylated (i.e., about 3EO) nonionic surfactant. 
The use of the compounds of the invention allows less alkoxylated nonionic 
to be used (i.e., provides an alternative). 
The Krafft Temperature of DHPG is set forth below: 
Krafft Temperature:8.degree. C. 
The detergency performance of DHPG, in triolein removal experiments at 
40.degree. C., with varying ratios of triethylene glycol mono-dodecyl 
ether (C.sub.12 EO.sub.8) and octaethylene glycol mono-dodecyl ether are 
shown in FIG. 1. DHPG on its own gives triolein removal of 55% which is 
comparable to C.sub.12 EO.sub.8 alone. Mixtures of DHPG and C.sub.12 
EO.sub.3 give a synergistic maximum is observed of 72% triolein removal. 
As expected mixtures of DHPG and C.sub.12 EO.sub.8 give no marked 
difference in detergency compared to the single surfactants. FIG. 2 shows 
the influence of temperature on triolein removal for DHPG alone; below 
40.degree. C. triolein removal decreases sharply, and above 40.degree. C. 
it appears to plateau at 60% removal. 
DHPG by itself was found to exhibit effective triolein removal (about 55%), 
which is comparable to C.sub.12 EO.sub.8. In combination with C.sub.12 
EO.sub.3 synergistic triolein removal of 72% is achieved. For DHPG alone 
triolein removal is dependent on temperature; below 40.degree. C. triolein 
removal decreases sharply, and above 40.degree. C. it appears to plateau 
at 60% removal. It also exhibits good foaming properties. 
The detergency efficacy of DHG (55% triolein removal when used alone) was 
comparable to C.sub.12 EO.sub.8. 
It should also be noted that detergency is affected by temperature at which 
it is conducted. Thus, while detergency by DHG alone at 40.degree. C. was 
55% triolein removal (Example 8), below 40.degree. C., triolein removal 
decreases sharply and, above 40.degree. C., it appears to plateau at 60% 
removal.