Detergent composition

A detergent composition containing as the surface active component the alkali metal or ammonium salts of a sulfonated C.sub.14 -C.sub.18 alkyl catechol admixture.

The present invention is directed to novel detergent compositions 
containing the alkali metal and ammonium salts of sulfonated C.sub.14 
-C.sub.18 alkylcatechols as the surfactant component thereof. 
It is known that long straight chain alkyl benzene sulfonates have been 
used as surfactants in detergent compositions heretofore. 
It has now been found that the novel detergent compositions of the present 
invention containing a specific surfactant component therein wherey 
improved detergency is obtained. 
The terms "surfactant" or "surface-active", which are used throughout this 
disclosure, are synonymous and refer to substances which, in solution, are 
used by themselves or in conjunction with cleaning adjuvants such as 
additives or builders to form detergent cleaning compositions. These 
detergent compositions are widely used as aqueous solutions to wet 
surfaces, remove soil, penetrate porous materials, disperse particles, 
emulsify oils and greases, etc., dependent upon the particular 
characteristics of the composition and the components thereof. 
The surfactant component thereof is a material or materials which is 
effective at low concentration levels in aqueous solutions and which can 
be produced in good yield from readily available low cost starting 
materials, is free from deleterious contaminants, is preferably easily 
handled, and are free-flowing liquids or powders. 
For many applications such as heavy duty industrial applications for metal 
scouring and dishwasher detergent compositions, the compositions 
necessarily include highly alkaline materials such as alkali metal 
hydroxides, alkoxides and phosphates. In the aqueous media that the 
detergent composition functions, the pH frequently will be from 10 to 13. 
For this reason a prerequiste of heavy duty industrial detergent 
compositions is its stability at elevated pH's in aqueous solutions. 
The detergent compositions of the present invention contain as the 
surfactant component from about 0.01 to about 10% by weight of the alkali 
metal or ammonium salts of sulfonated C.sub.14 -C.sub.18 alkyl catechols 
including mixtures thereof, from about 80 to about 40% by weight of a 
water soluble inorganic builder material or builder materials, that is 
normally one or more of known inorganic salts, acids and/or bases, such as 
the alkalis, phosphates and silicates of the alkali metals including 
ammonium or the corresponding neutral salts of mixtures thereof. The 
composition may also contain from about 0 to about 15 to 20% by weight of 
organic builder material or materials that impart to the composition 
foaming power and/or emulsifying power, or have a soil-suspending function 
in the composition. Suitable organic builder materials include sodium 
carboxymethylcellulose, ethylenediamine-tetraacetic acid and fatty 
monoethanolamides and the like. 
The detergent composition may further contain relatively minor amounts, on 
the order of from about 0.5 to about 5% by weight of special purpose 
components such as one or more of the lower alkanols, glycols, ethers that 
function as solubilizing agents, as well as known bleaching agents or 
brighteners which are dyestuffs that do not absorb or reflect light in the 
visible range of the spectrum. The surfactant component of the detergent 
composition is an alkali metal or ammonium salt or salts of a sulfonated 
C.sub.14 -C.sub.18 alkylcatechol or mixed sulfonated C.sub.14 -C.sub.18 
alkylcatechols. 
The catechol is present in the admixture in a weight ratio of from about 50 
to 70 parts of mono (C.sub.14 - C.sub.18) alkyl catechol and from about 50 
to 30 parts of di (C.sub.14 - C.sub.18) alkyl catechol. 
The surfactant component is prepared in the following manner:

EXAMPLE I 
A hexadecylcatechol mixture was obtained by reaction of one mole of 
1-hexadecene with two moles of catechol in the presence of 10% by weight 
of "Amberlyst 15", (a sulfonic acid cation exchange resin having a 
macroreticular structure and being obtained from Rhom & Haas,) as a 
catalyst and consisted essentially of about 70% mono-hexadecyl catechol 
and about 30% of di-hexadecyl catechol, by analysis. 
This admixture in an amount of 19.7 grams was added slowly to 75 grams of 
concentrated sulfuric acid to keep the temperature below 20 C. The 
reaction mixture was then heated to 90.degree. C. for 5 minutes while 
maintaining the reactants under a nitrogen atmosphere. The resulting 
reaction solution was then cooled to 10.degree. C., and 25 ml. of water 
followed by a solution of 60 grams of sodium hydroxide in 150 ml. water 
were added slowly so as to keep the temperature below 30.degree. C. The 
reaction mixture was then stripped to dryness on a rotatory evaporator 
under vacuum. The solids thus formed were extracted four times using per 
extraction, 150 ml. of ethanol, the ethanol stripped and the product 
extracted once with methanol. Analysis of the solids confirmed the product 
was the sodium salt. 
EXAMPLE II 
Another portion of the same hexadecylcatechol mixture as used in Example I 
above was sulfonated at 70.degree. C. for 5 minutes as in Example 1, 
above. The sulfonated catechol mixture was added slowly to a solution of 
9.0 g. of sodium metal in 250 ml. of ethanol so as to keep the temperature 
between 10.degree.-20.degree. C. The resulting reaction solution was then 
filtered and the ethanol stripped therefrom. The product was identified as 
the sodium salt of sulfonated hexadecycatechol. 
The effectiveness of each of the above prepared surfactants was determined 
in the following tests carried out in a laboratory Launder-Ometer. 
The procedure used was to immerse sized swatches of standard soiled cotton 
cloth in 200 ml. of an aqueous wash solution containing 0.1 and 0.2% by 
weight of the surfactant for 10 minutes while maintaining the solution at 
60.degree. C. Duplicate runs were made at each concentration range and 
builder materials were also present in some tests. For purposes of 
comparison similar tests were carried out on commercial detergents. 
The wash solutions were prepared from distilled water and had been treated 
to provide a water hardness of 3165 ppm as calcium carbonate (185 grains). 
The washed cloth swatches were removed from the test solution containers, 
rinsed, dried and the relative degree of whiteness measured using a 
Photovolt Reflectometer in accordance with known practice. 
The data obtained with the Reflectometer were recorded and averaged for the 
two runs at each concentration to obtain an average Reflectance for the 
washed cloth. This value was converted to an "Average Detergency 
Coefficient", (ADC) value, determined by expressing the soil removal 
properties of each of the test compositions as a percentage of the results 
with a known standard detergent composition. 
The test results (ADC) are set forth in the following Table together with 
additional particulars, if applicable, to the compositions of the wash 
solutions. 
__________________________________________________________________________ 
TEST RESULTS 
Additional 
Detergent/Builder 
Example 
Additive Additive Ratio ADC 
__________________________________________________________________________ 
3. Product of Ex I 
-- -- 134 
Comparative 
Commercial sodium 
-- -- 100 
Ex. A salt of C.sub.14 --C.sub.18 
olefin sulfonate 
4. Product of Ex I 
-- -- 146 
Comparative 
Commercial linear 
-- -- 100 
Ex. B alkylbenzene sulfonate 
5. Product of Ex II 
-- -- 183 
Comparative 
Commercial sodium 
-- -- 100 
Ex. C salt of C.sub.14 --C.sub.18 
olefin sulfonate 
6. Product of Ex II 
Sodium tetra pyro- 
30/70 129 
phosphate builder 
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In the above Table the test results obtained from runs made at separate 
times are reported. The grouping of the runs made at the same time is 
evident from the appearance of the table, the separation between each pair 
of Examples except for the last three, showing different run dates. 
Comparison Examples A and C used the same sodium salt of a C.sub.14 
-C.sub.18 olefin sulfonate. 
Inspection of the data show that the surfactant components of the detergent 
compositions are effective as detergents alone or in combination with 
inorganic builders. The data further show the degree of effectiveness of 
the materials in comparison with two types of commercial detergents. 
Representative formulae for the compositions of the present invention are 
for Example, for Laundry Machine use, 0.01 - 10% of Example I or Example 
Ii surfactants, 20-40% by weight of sodium tetrapyrophosphate, 20-30% 
sodium silicate, 10-20% of sodium carbonate, 1-3% of sodium 
carboxymethylcellulose, and 0-10% of starch; for automatic dishwasher use, 
about 5-12% of the surfactant, about 10-40% sodium stearate and 55-78% 
sodium tetrapyrophosphate. The alkali metal and ammonium salts of the 
sulfonated C.sub.14 -C.sub.18 alkyl catechols of the present invention can 
be prepared in a known manner such as by reacting a C.sub.14 -C.sub.18 
alkene with catechol in the presence of an alkylation catalyst to form a 
mixture of mono (C.sub.14 -C.sub.18) alkyl catechol, and di (C.sub.14 
-C.sub.18) alkyl catechol, sulfonating said formed mixture with 
concentrated sulfuric acid, thereafter converting the sulfonated mixture 
to the alkali metal or ammonium salts by treatment with aqueous sodium or 
ammonium hydroxide or with sodium metal in ethanol.