Patented June 10, 1952

2,599,553

UNITED STATES PATENT OFFICE

2,599,553
COMPLEX ALUMNUMI SOAP
Bruce W. Hotten, Richmond, Calif., assignor to
California Research Corporation, San Fran
cisco, Calif., a corporation of Delaware
No Drawing. Application February 17, 1950,
Serial No. 144,850
8 Claims, (C. 260-414)
2
This invention relates to new aluminum mixed designated as “relatively oleophilic' anions, and
Organic anion soaps (e. g., aluminum benzoate the organo anions of lesser oil solubility will be
stearate), i. e., aluminum soaps having anions designated as "relatively oleophobic' anions.
derived from more than one organic acid, par The Organo anions are derived from Organic
ticularly anions derived from organic acids dif acids, one of which is "relatively oil-soluble'
fering Substantially in oil Solubilities. and another of which is 'relatively oil-insoluble.'
It is a primary object of this invention to pro That is, the Organo acids of the relatively oleo
vide as a new class of compounds aluminum Soaps philic anions are relatively oil-soluble, while the
having mixed organo anions. organo acids of the relatively oleophobic anions
It is a further object of this invention to pro O are relatively oil-insoluble, i.e., less oil-soluble as
vide a class of aluminum Soaps having new and compared to the oleophilic organo acids.
unique properties. The aluminum di-soaps of the more soluble
These and other objects of this invention will organo anions (i. e., the relatively oleophilic
be apparent from the ensuing description and anions) are soluble in an amount of at least 5%
the appended claims. 5 (by volume) at 400 F. in a petroleum. White oil
It has been discovered that certain aluminum having viscosity characteristics of 346 SSU at
mixed organic anion soaps possess valuable and 100°F. and 54 SSU at 210° F. and having a vis
apparently unique properties. cosity index of 92. That is, at 400° F., 5% of
It has long been believed that the organo the aluminum soap of the oleophilic Organo
anions of aluminum Soaps should be identical in 20 anion will form a true solution in the petroleum
Order to obtain aluminum soaps of sufficient oil white oil. On the other hand, the aluminum
Solubility to form proper gel structure and to soaps of the less soluble organo anions (i. e., the
impart characteristic properties to greases, to relatively oleophobic anions) are soluble in the
serve as fillers for inks, to impart desired flatting above white oil in an amount of less than 1%
characteristics to paints, etc. However, it has 25 at 400° F. That is, at 400° F., less than 1%
noW been found that the mixed organic anion (from 0% to about 1%) of the aluminum Soap
aluminum Soaps of this invention (i.e., the com containing the oleophobic anions will dissolve in
plex aluminum soaps) have numerous advan the white oil to form a true solution.
tages Over the aluminum Soaps having identical The aluminum di-soaps of each of the organo
Organic anions. 30 anions (i. e., the aluminum di-soaps of the oleo
The complex aluminum soaps are particularly philic anion and the aluminum di-Soaps of the
useful in greases. These soaps impart to the oleophobic anion) are insoluble in water. For
grease composition high melting point and re example, in the aluminum-benzoate-stearate
sistance to emulsification in water, as set forth soap, which is an example of a complex alumi
in the United States patent application Serial 35 num soap of this invention, the aluminum di
No. 112,584, filed August 26, 1949, of which ap soap of the benzoate anion (i. e., aluminum di
plication this is a continuation-in-part. benzoate) and the aluminum di-soap of the
The Soaps of this invention are useful as flat stearate anion (i. e., aluminum di-stearate) are
ting agents for surface-coating materials, as de insoluble in Water.
tergents, as emulsifying agents (water-in-oil type 40 Furthermore, the aluminum soaps of the rela
emulsions especially), as water proofing and tively oleophobic anions melt at a temperature
fungistatic agents for fabrics, as concrete cur about 400° F., and the aluminum soaps of the
ing agents, as hardening agents, as thickening relatively oleophilic anions melt at a temperature
agents in paints and inks, etc. less than 350° F.
The present complex aluminum soaps contain 45 The complex aluminum soaps of this inven
at least two dissimilar substantially hydrocar tion are polymeric in structure, that is, the con
bonaceous Organic anions having certain char plex aluminum soaps have more than one alumir
acteristics. The organo anions are generally num atom and at least two dissimilar Organ.0
oleophilic; however, one of the organo, anions anions throughout the polymeric structure. It
of the complex soap molecule. has a greater oil 50 is possible for the complex aluminum Soaps to
Solubility than the other organo anion of the contain as many as 1,000 or more monomeric
same soap molecule. For purposes of simplifica units, each monomeric unit containing one alumi
tion of the discussion of the characteristics of the num atom having all of its valences satisfied by
organo anions of the complex aluminum soap, 55 at least one hydroxyl group and two organo
the organo anions of greater oil solubility will be anions. Thus, it is readily understood that al
 2,599,553
3 4
though aluminum has a valence of --3, it is not tuted acids of phosphorus, e.g., phenyl phosphate,
meant herein to limit the complex aluminum an Organic Substituted acid of boron, e. g.,
Soap of this invention to one containing only methane boronic acid, or in some cases an anion
three specific anions. In the over-all average, of an organic substituted acid of silicon, e. g.,
the valence bonds of the aluminum atoms can benzene siliconic acid. For example, the oleo
be directed to more than three specific anions, phobic anion portion of the average molecule may
that is, to more than one hydroxyl anion and Contain, in part, an organo-phosphate (-PO4R)
more than two organo anions. The average anion, wherein R is an organic radical.
molecule in the soap may contain a plurality of Suitable oleophobic anions are derived from:
relatively oleophilic anions or a plurality of rela O benzoic acid, methyl benzoic acid, ethyl benzoic
tively oleophobic anions per aluminum atom. For acid, toluic acid, phenyl acetic acid, phenyl
example, it may be advantageous in Some in propionic acid, Oxalic acid, malonic acid, iso
stances to use a complex aluminum Soap as ex Succinic acid, glutaric acid, adipic acid, pimelic
emplified by aluminum benzoate-stearate-capryl acid, Suberic acid, azelaic acid, Sebacic acid,
ate. phthalic acid, Salicylic acid, carboxy-methyl
Suitable relatively-oleophilic anions are anions cellulose, polyacrylic acid, etc.
of certain aliphatic (saturated and unsaturated), The ratio of the oleophobic to the oleophilic
alkaryl, aralkyl, and alkyl-substituted cycloali anions in the soap of this invention can vary de
phatic carboxylic acids, and organo-Substituted pending upon the purpose for which the Soap is
acids of sulfur and/or phosphorus. The acids 20 used. The more oil-soluble organo anions (i. e.,
must be Sufficiently aliphatic and hydrocarbona the relatively oleophilic group) and the less oil
ceous in character to impart the defined oil Soluble organo anion (i.e., the relatively oleo
solubility. Thus, suitable aliphatic carboxylic phobic group) are present in such proportions
acids contain from 8 to about 30 carbon atoms, to each other as to be of utmost effectiveness for
preferably from 12 to 18 carbon atons. The the desired use. For example, when the complex
aliphatic substituent in the various cyclic car SOap Of this invention is used to modify the
boxylic acids should contain from about 4 to properties of grease compositions, that is, to in
about 20 carbon atoms on the aliphatic group part high melting point and resistance to emulsi
attached to the ring. The aralkyl, alkaryl, and bility in Water to the grease composition, the ratio
cycloaliphatic carboxylic acids preferably con 30 of the oleophobic anion to the oleophilic anion
tain a total of about 16 carbon atoms. The (on an average molecule basis) can be altered
relatively oleophilic anion can also be derived So that the desired grease structure Will be ob
from substituted phenols; that is, the oleophilic tained in lubricating oils of varying solvency
anion may be an alkyl phenol containing at least characteristics. The ratio of oleophobic anions
4 carbon atoms in the alkyl group, preferably 16 35 to the oleophilic anions in the average soap mole
carbons in the alkyl group; e. g., cetyl phenol. cule may vary from 1:10 to 10:1.
It is preferred that the organo-substituted AS Stated, the number of free hydroxyl groups
acids of Sulfur and phosphorus contain from present in the aluminum soaps of this invention
about 14 to about 36 carbon atoms in the organo Can range from 1 to 2 hydroxyl groups for each
substituent. The oleophilic acid anions may con 40 aluminum atom in the soap. As the number of
tain various Substituents, such as chlorine, hy free hydroxyl groups present decreases and be
droxy, amino, alkoxy, e. g., methoxy, and the comes Substituted by organic groups, the complex
like radicals, so long as the anion remains sub aluminum Soap becomes more acidic, and more
stantially hydrocarbonaceous in character. easily dispersed in mineral oil type solvents. As
Examples of the carboxylic acids from which the number of free hydroxyl groups increases, the
the oleophilic anions are derived are caprylic complex aluminum Soap becomes more basic, and
acid, capric acid, lauric acid, myristic acid, more easily dispersed in polar type solvents, e.g.,
palmitic acid, Stearic acid, 12-hydroxy stearic glycols, carbitols, etc.
acid, arachidic acid, Inelissic acid, oleic acid, It is known that the third “OH' group of
linoleic acid, butyl benzoic acid, hexyl benzoic Al(OH)3 is most difficultly displaced or neutral
acid, octylbenzoic acid, decylbenzoic acid, phenyl ized; in fact, the third “OH' group is not dis
butyric acid, phenyl hexanoic acid, phenyl deca placed by fatty acids. However, the small basic
noic acid, cetyl benzene sulfonic acid, didodecyl effect of the remaining “OH' group may be neu
benzene Sulfonic acid (a dipolypropylene benzene tralized in effect by the attachment of a fatty
Sulfonic acid), an alkane phosphonic acid having 55 acid to the Soap molecule. When an aluminum
from about 24 to about 36 carbon atoms in the "tri-Soap' (e. g., aluminum “tri-stearate') is
alkane group, cetyl thiophosphoric acid, naph formed, the third “OH' group is still present,
thenic acids, etc. The third acid molecule attaches to the alumi
The relatively oleophobic anions are Substan nun Soap molecule by means of a hydrogen
tially hydrocarbonaceous in Structure and can be 60 bonding effect, apparently neutralizing the small
selected from anions of certain aliphatic (satu basic effect of the remaining “OH' group. Per
rated and unsaturated), aromatic, aralkyl, alkaryl aluminum atom, up to 1 mol of acid may be
and cycloaliphatic mono- and polycarboxylic loosely bound to the soap molecule.
acids. Suitable aliphatic monocarboxylic acids Examples of complex aluminum soaps of this
contain from 4 to 7 carbon atoms, and dicar 65 invention are: aluminum benzoate stearate, alu
boxylic acids contain from 4 to 20 carbon atoms, minum benzoate di-stearate, aluminum benzoate
So long as the aluminum di-Soap of the oleophobic oleate, aluminum benzoate 12-hydroxy stearate,
anion resulting therefrom has a solubility in aluminum toluate stearate, aluminum benzoate
white oil of less than 1%. The alkyl groups of naphthenate, aluminum benzoate hydrogenated
the aralkyl and alkaryl carboxylic acids contain rosin, aluminum benzoate sulfonate, aluminum
no more than 3 carbon atoms. Thus, the alkaryl aZelate Stearate, aluminum allizarinate stearate,
and the aralkyl carboxylic acids contain a total aluminum phosphate benzoate stearate, alumi
of not more than 9 carbon atoms. nun benzoatehydroxy stearate, etc.
The oleophobic anions of the complex alumi The complex aluminum soaps of this invention
num Soaps can also be anions of Organic Substi 75 can be prepared according to methods involving
 2,599,558
co-precipitation. For example, aqueous solutions acid and 16.8 parts by weight of potassium hy
mixtures of the water-soluble soaps (e.g., so droxide was dissolved in about 500 parts by
d soaps) in the desired proportion of rela Weight of water at 150 F., forming a clear Solu
tively oleophilic and relatively oleophobic anions tion. To this solution was added 33.3 parts by
are admixed with an aqueous solution of an alu Weight of aluminum Sulfate Octadecahydrate dis
minum salt (e.g., aluminum sulfate). The re Solved in about 300 parts by weight of water.
sulting precipitate of the complex aluminum soap The resulting aluminum benzoate stearate was
is then preferably purified to remove the salts obtained by filtering, washing and drying the
such as sodium sulfate. precipitate as above in Example 1. On ashing,
When the complex-aluminum soap has been 10 the soap left 11.6%, Al2O3 (theoretical for
precipitated from its reaction medium (e. g., AlC24H39O5=11.4%).
water), it is desirable that this complex alumi Eacample 4-Preparation of aluminum ben2Oate
num soap precipitate be removed from the re Stearate (benaoate/stearate ratio-0.1)
action medium-assoon as possible.
-Complex aluminum soaps may also be pre A mixture of 1.22 parts by weight of benzoic
pared in situ according to the method described acid, 27 parts by Weight of commercial stearic
in Jones Patent No. 2,469,041, wherein it is acid and 9.24 parts by weight of potassium hy
taught that a fatty acid (e.g., stearic acid) can droxide Was dissolved in 600 parts by weight of
be added to a mineral oil solution of an alumi Water at 125° F. To this solution was added
nun alcoholate (e. g., altiminum butoxide) to 20 22 parts by Weight of aluminum nitrate nono
form an aluminum stearate, except that in the hydrate dissolved in 400 parts by weight of water.
preparation of the complex aluminum Soaps a The resulting aluminum benzoate stearate was
mixture of fatty acids is used. obtained by filtering, Washing and drying the
In the formation of the complex aluminum precipitate as above in Example 1. On ashing,
soaps of this invention, it is desirable that less the soap left 10.1%. Al2O3 (theoretical-9.4).
than one equivalent of the aluminum inorganic Eacample 5.-Preparation of aluminum beneoate
compound react with a total of about one equiva Stearate (benaoate/stearate ratio-10)
lent of the saponifiable Organic material (e. g.,
the organic acids) noted hereinabove. A mixture of 12.2 parts by weight of benzoic
The following examples illustrate the prepara 30 acid, 2.7 parts by weight of commercial stearic
tion of the complex aluminum Soaps of this acid and 9.24 parts by Weight of potassium hy
invention. droxide was dissolved in about 600 parts by
Weight of Water at about 125° F. To this solu
Eacample 1.-The preparation of aluminum a2e tion was added 22 parts by weight of aluminum
late Stearate nitrate nonohydrate in 400 parts by weight of
A mixture of 13.5 parts by weight of commer Water. The resulting aluminum benzoate stear
cial stearic acid (approximately 60% stearic acid ate was obtained by filtering, washing and dry
and the remainder mainly palmitic acid) and 10 ing the precipitate as above in Example 1. On
parts by weight of azelaic acid was dissolved in ashing, the soap left 15.5% Al2O3 (theoretical
400 parts by weight of water at approximately 40 16.2).
180° F. This solution was slowly added, with Eacample 6.-Preparation of aluminum beneoate
stirring, to a solution of 24.9 parts by weight of 12-hydroary stearate
aluminum sulfate octadecahydrate in 300 parts
by weight of water at this same temperature. A mixture of 28.8 parts by weight of sodium
The resulting reaction mixture was filtered. The benzoate, 48 parts by weight of 12-hydroxy
white precipitate which was formed during the Stearic acid and 13.6 parts by weight of sodium
reaction was washed with water by adding the hydroxide Was dissolved in about 500 parts by
white precipitate to a large amount of water and weight of Water at 150° F., forming a clear solu
then stirring vigorously. The precipitate was tion. To this solution was added 68 parts by
washed in this manner three separate times until 50 Weight of aluminum nitrate nonohydrate dis
only a faint positive sulfate ion test was attained Solved in about 300 parts by weight of Water.
in the filtrate from the third wash. The re The resulting aluminum benzoate hydroxystear
sulting mixed soap was then dried at a tempera ate was obtained by filtering, washing and drying
ture ranging from 210 F. to 250 F., was pow the precipitate as shown above in Example 1.
dered and passed through a No. 60 mesh sieve. 55 Eacample 7-Preparation of aluminum beneoate
EEample 2-Preparation of aluminum toluate naphthenate
Stegrate
A mixture of 14.4 parts by weight of sodium
A mixture of 28.6 parts by weight of toluic acid benzoate, 31 parts by weight of naphthenic acid
containing a 2:1 mixture of the meta and para 60 (molecular weight-280; 90% saponifiables) and
isomers, 27 parts by weight of commercial stearic 8 parts by Weight of sodium hydroxide was dis
acid, and 18 parts by weight of sodium hydroxide Solved in about 500 parts by weight of water at
was dissolved in 400 parts by weight of water at 150 F., forming a clear solution. To this solu
about 180° F. This solution was slowly added, tion was added 37.5 parts by weight of aluminum
with stirring, to 50 parts by weight of aluminum nitrate nonohydrate in about 300 parts by weight
sulfate octadeca-hydrate in 300 parts by weight of Water. The resulting aluminum benzoate
of water at the same temperature. The resulting naphthenate was obtained by filtering, washing
complex polyvalent metal soap was filtered, and drying the precipitate as shown above in
washed and dried as described in Example 1. On Example 1.
ashing, the soap left 13.9%. Al2O3 (theoretical for Eacample 8-Preparation of aluminum beneoate
the aluminum toluate stearate is 13.6%). alkyl benzene sulfonate
Eacample 3-Preparation of aluminum benzoate A mixture of 14.4 parts by weight of sodium
stearate (benaoate/stearate ratios 1.0) benzoate, 74.6 parts by weight of sodium alkyl
A mixture of 12.2 parts by weight of benzoic 75 benzene sulfonate (70% of which was a sodium
acid, 27.1 parts by weight of commercial stearic didodecyl benzene Sulfonate and 30% of which
 2,599,553
7 8 m
was unsulfonated di-dodecyl benzene) and 4.0 that When a mixture of 12 parts by Weight of a
parts by Weight of sodium hydroxide was dis complex aluminum soap (e. g., aluminum benzo
Solved in about 500 parts by Weight of Water at ate Stearate) Was heated together at 450° E. With
150 F., forming a clear Solution. To this Soul 108 parts by Weight of a California solvent-re
tion WaS added 33.3 parts by Weight of aluminum 5 fined parafiinic base oil having a viscosity of 485
nitrate nonohydrate dissolved in about 300 parts SSU at 100 F., a grease was obtained which was
by Weight of Water. The resulting aluminum light brown, translucent, and which had an
benzoate alkyl benzene Sulfonate Was obtained ASTM dropping point of 400-- F. A five-gram
by filtering, Washing and drying the precipitate Sample of the grease remained fully intact with
as ShoWn above in Example 1. The resulting O Out any disintegration. When immersed in boiling
Soap contained. Some oil in the form of unsulfo Water for One hour.
nated alkyl benzenes, which caused the Soap The Surface activity of the complex aluminum
to be SOmeWhat gummy. Because of this gum Soaps of this invention is adequately illustrated
niness, it was necessary, When dispersing the by the following simple emulsification test where
Soap in oil to form a grease, to use petroleum 5 in Solutions containing 1% of each of the soaps
ether in assisting the dispersion. The petroleum to be tested in Pearl oil 1 where shaken uniformly
ether Was boiled Off during the preparation. Of With equal Volumes of Water in 10 ml. graduated
the grea.Se. cylinders. The cylinders Were allowed to stand
Eacample 9-Preparation of aluminum benzoate for One hour, after which time the volume of the
phosphate Stedrate separated lower layer was measured. The foll
lowing Table II presents results obtained in this
A mixture of 8.2 parts by Weight of benzoic emulsification test.
acid, 18.0 parts by Weight of commercial Stearic TABLE II
acid, 8.4 parts by Weight of tri-Sodium phosphate,
and 13 parts by Weight of potassium hydroxide 25 Toluate Wolume of
was dissolved in about 500 parts by weight of No. Soap Sulfonate E.
water at 150° F., forming a clear Solution. To Ratio Separated
this solution was added 40 parts by Weight of
aluminum nitrate nonohydrate dissolved in about ini.
300 parts by weight of water. The resulting - - - None.------------------------------------------- 5
30 2- - - Al Egate Alkyl Benzene Sulfo- O 2
aluminum benzoate phosphate Stearate Was ob late.2
tained by filtering, Washing and drying the pre 3- - - Al Eliate
nate.2
Alkyl Benzene Sufo. 0.5 0
cipitate as above in Example i. 4--- Al late.2
Eliate Alkyl Benzene Sulfo- t 3.
Eacample 10-Preparation of aluminum aliedri 5- - - Al Toluate
nate.2
Alkyl Benzene Sulfo- 2 4.
nate Stedrate 35
A mixture of 12 parts by Weight of allizarin,
26.7 parts by weight of commercial Stearic acid The data set forth in above Table II illustrates
and 16.8 parts by weight of potassium hydroxide the remarkable effectiveness of the complex alu
were added to about 200 parts by weight of water minum Soaps, e. g., aluminum toluate sulfonate,
40 particularly Wherein the toluate-sulfonate ratio
and heated to 180° E. To this Solution Was added
40 parts by weight of aluminum nitrate nonohy is 1:2, as an emulsifying agent in a water-oil
drate dissolved in 100 parts by Weight of Water. System.
The resulting aluminum allizarinate Stearate (a Eacample 11-Preparation of aluminum, toluate
deep-brown-red precipitate) was obtained by alkyl beneene Sulfonate (toluate/sulfonate
filtering, Washing and drying the precipitate aS ration 1.0)
above in Example i. A mixture of 7 parts by weight of toluic acid,
X-ray diffraction patterns of the complex alu 55 parts by Weight of sodium alkyl benzene sul
minum Soaps of this invention Were obtained to fonate (43% of which was a sodium didodecyl
establish the identity of these SoapS aS true Con 50 benzene Sulfonate and 57% of which was unsul
pounds. The following Table I represents the fonated didodecyl benzene) and 5.6 parts by
inter-atomic distances, as determined by the Weight of potassium hydroxide was dissolved in
X-ray diffraction patterns, of aluminum diben about 200 parts by weight of water and 200 parts
Zoate OHA (benzoate)2], aluminum distearate by Weight of 95% ethyl alcohol at 150° F., form
OHA (Stearate) 2 and a member of the new 55 ing a clear Solution. To this solution was added
class of compounds, aluminum benzoate Stearate 19 parts by Weight of aluminum nitrate nono
OHA1 (benzoate) (Stearate). hydrate dissolved in about 100 parts by Weight
TABLE I of Water. The resulting aluminum toluate di
dodecyl benzene Sulfonate was obtained by fil
Annun Aninth
y Aunainum 60 tering, Washing and drying the precipitate as
Compound Dibenzoate Distearate | Bo
SE shown above in Example 1.
The complex aluminum Soaps are useful as
D D D flatting agentS in paints and varnishes. Here
Interatomic Distances in
Angstrom Units (D) and
10.7
5.4
8 3.8
7.7
6
3
4.9
2.94 2
3 tofore, aluminum Stearate has been one of the
Relative Line Intensities 3.22 0 3. 83 4 2.06 -- most effective flatting agents for paints and war
(I). 1.26 0 nishes; however, its low gelling temperature has
made it necessary to incorporate the aluminum
As noted hereinabove, the complex aluminum Stearate into the vehicle by slow grinding. With
soaps of this invention are useful for numerous the use of a complex aluminum soap, the soap
purposes. The use of the complex aluminum may be incorporated into the vehicle by the more
soaps to raise the melting point of a grease con Pearl pil is a kerosene fraction haying an initial ASTM
position and to increase the resistance of the (D-86) distillation point of about 348 F., a 50% distill
grease to water emulsibility is set forth in the lation point of 415 E. and an end point of 52° E.
aforementioned Hotten-Echols U. S. patent ap The aluminum teluate alkyl benzene sulfonate of Example 1.
below is are example of the aluminurn touate alkylbenzene sulfonate
plication Serial No. 112,548, wherein it was shown used in these tests.
 2,599,558
9 O
desirable fast mill grinding and obtain a flatting organo anion derived from a carboxylic acid the
effect for paints and warnishes equivalent to or aluminum di-soap of which acid is characterized
better than the formerly used aluminum di by a white oil solubility of less than 1% at 400°F.
Stearate. The following Table III presents data, 3. An aluminum soap having at least two un
to Show the effect of complex aluminum SOaps as 5 like organo anions, one organo anion derived
flatting agents in paints and varnishes. Metal from a fatty acid the aluminum di-Soap of which
strips were coated with 1% suspensions of the acid is characterized by a White oil Solubility of at
soaps in black enamel, and the gloSS resulting least 5% at 400° F., and another organo anion
therefrom tested in a gloss meter according to derived from an organic acid the aluminum di
Procedure A of the ASTM specification D523-44T. 10 soap of which acid is characterized by a white
In the gloss meter, a photoelectric cell registered oil solubility of less than 1% at 400 F.
the amount of light reflected from the paint 4. An aluminum soap having at least two un
Surface. like organo anions, one organo anion being an
TABLE III anion Selected from the group of aromatic car
15 boxylic acid anions containing from 1 to 3 non
Flatting Agent Glossi
eSS aromatic carbon atoms, and another Organo
anion being selected from the group of aliphatic
acid anions containing from 8 to 30 carbon atoms.
None---------------------------------------------------- 100
5. The aluminum Soap of claim 4, Wherein the
Aluminum di-stearate.-----------
Aluminum benzoate Stearate ---------------------------
Aluminum benzoate Stearate ---------------------------
23
22
20 aromatic carboxylic acid anion is derived from
benzoic acid, and wherein the aliphatic acid anion
i The benzoate stearateratio was 1:2.
is derived from Stearic acid.
The benzoate stearate ratio was . 6. The compound, aluminum benzoate Stearate.
I claim: 7. The compound, aluminum toluate stearate.
25 8. The compound, aluminum toluate didodecyl
1. An aluminum Soap having at least two un benzene Sulfonate.
like organo anions, one organo anion derived BRUCE. W. HOTTEN.
from an Organic acid the aluminum di-Soap of
which acid is characterized by a white oil solubil REFERENCES CITED
ity of at least 5% at 400° F., and another organo 30 The following references are of record in the
anion derived from an organic acid the alumi file of this patent:
num di-soap of which acid is characterized by a
white oil solubility of less than 1% at 400' F. UNITED STATES PATENTS
2. An aluminum Soap having at least two un Number Name Date
like Organo anions, One Organo anion derived 35 2,345,061 Miles -------------- Mar. 28, 1944
from a carboxylic acid the aluminum di-Soap 2,417,071 Gebhart et al. ------ Mar. 11, 1947
of which acid is characterized by a White oil 2,447,064 Gebhart et al. ------ Aug. 17, 1948
Solubility of at least 5% at 400 F., and another 2,456,824 Fischer ------------ Dec. 21, 1948