US 2203642 A
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Description (OCR text may contain errors)
Patented June 4, 1940 PATENT oFF cr.
SULPHONATION PRODUCT Roland Kal i Newark, N. J., assignor to National Oil Products Company, Harrison, N. J., a corporation of New Jersey No Drawing.
The invention relates, in general, to new chemical compounds and, in particular, to sulphonation products of certain esters of naphthenic acids.
Notwithstanding the great number of emulsifying, dispersing and wetting'agents known and available on the market, there is a constant need for new agents of this type having novel and improved properties. Many materials which could be employed'to great advantage in an emulsified form cannot be emulsified satisfactorily due to the inadequacy of the emulsifiers heretofore known. Such materials include inter alia the polyvalent metal soaps of naphthenic acids such,
for example, as lead naphthenate, copper naphthenate or other metallic naphthenates and insoluble metallic soaps.
The general object of the invention is to provide new chemical compounds useful as emulsify- 0 ing, dispersing and wetting agents.
A specific object of the invention is to provide new compounds particularly adapted to emulsify water-insoluble soaps of naphthenic acids and other materials ordinarily difiicult or impossible to emulsify.
Anotherobject of the invention is to provide new compounds having improved wetting power for use as textile assistants.
Other objects of the invention will in part be obvious and will in part appear hereinafter.
I It has now been discovered that when certain esters of naphthenic acids are subjected to sulphation, products are obtained which possess remarkable emulsifying, dispersing and wetting properties. Hence, the invention comprises, as
new compounds and as new emulsifying, dispersing and wetting agents, sulphation products of esters of naphthenic acids with an unsaturated compound containing 8 or more carbon atoms.
selected from the group/consisting of fatty alcohols, hydroxy fatty acids and hydroxy fatty esters. The process of the invention comprises esterifying naphthenic acid with an unsaturated compound containing 8 or more carbon atoms,
selected from the group consisting of fatty alcohols, hydroxy fatty acids and hydroxy fatty esters and sulphating the resulting ester.
The invention accordingly comprises the several steps and the relation of one or more of such steps with respect to each of the others, and the product possessing the features, properties and the relation of characteristics, all as exemplified in the detailed disclosure hereinafter set forth and the scope of the invention will be indicated 66 in the claims.
Application October 23, 1937, Serial No. 170,596
The expression naphthenic acids" is employed herein to designate the mixture of acids of that name currently obtained in petroleum refining, as
well as naphthenic acid or acids which are synthetically prepared or otherwise obtained. It is 5 preferred, however, to use the naphthenic acids derived from the refining of petroleum in view of their relatively low cost.
The first step in the process of producing the products of 'the invention comprises esterifying 10 naphthenic acids with a hydroxy fatty acid, such as ricinoleic acid, or with a suitable derivative thereof such as castor oil or other esters of ricinoleic acid or hydroxy fatty acids. In lieu of the above hydroxy compounds, mono-hydroxy fatty alcohols containing 8 or more carbon atoms. or substituted derivatives thereof, may be used. It
is preferred, however, to esterify the naphthenic acids with hydroxy fatty acids or their hydroxy derivatives.
The esterification may be carried out by direct reaction of the naphthenic acids and the abovementioned hydroxyl-containing compounds at elevated temperature, with or without the aid of catalysts, or by reaction of potassium or sodium 25 naphthenate with the chloride produced from the hydroxy compounds, or' by other known methods.
- The sulphating agents which may be used in the treatment of the above-mentioned esters are well-known to the art and include sulphuric acid, chlorsulphonic acid, oleum, etc. The sulphation may be carried out on the esters themselves or on solutions of the esters in inert solvents such as chlorinated hydrocarbons, according to 35 any of the well-known sulphation procedures used in the preparation of sulphated fatty oils.
For a fuller understanding of the nature and objects of the invention, reference should be had to the following examples which are given merely 4 to illustrate some of the products of the invention and method of making the same, and in no way should they be construed in a limiting sense.
Example I is obtained after separation of the water has outstanding emulsifying properties for metallic naphthenates and metallic soaps, and may of course be used as an emulsifying agent for other materials, if desired.
Example II 100 lbs. of oleyl naphthenate are sulphated for hours withsio lbs. of 66 B. sulphuric acid, at a temperature of about 20 C. The sulphation mass is then washed with 300 lbs. of a solution of sodium chloride and neutralized with sodium hydroxide. After overnight standing, the lower water layer is discarded. The upper layer, consisting of sulphated oleyl naphthenate, is particularly useful as a penetrating, finishing and wetting agent for textile treatments.
Example III 100 lbs. of the ester obtained by reaction of ricinoleic acid and naphthenic acids at elevated temperatures is sulphated for 4.hours at 30 C. with 30 lbs. of sulphuric acid.
The sulphation mass is washed and neutralized as described in Example I. The sulphated-product obtained in this manner has. the same uses as the products obtained in Examplev I or II.
The sulphated esters of the invention possess new and valuable emulsifying and dispersing properties, and they are admirably suited for emulsifying or dispersing materials which are otherwise difiicult or impossible to emulsify, such for example, as lead naphthenate, copper naphthenate and other polyvalent metal naphthenates and insoluble metallic soaps.
The above properties make the products of the invention of great value for the preparation the treatment of leather and other materials where good penetrating action is required.
1? Since certain changes in carrying out the above process and certain modifications in the product which embody the invention may be made without departing from its scope, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limitmg sense.
, Having described my invention, what I claim as new and desire to secure by Letters Patent is:
1.'A sulphation product of an ester'of naphthenic acids with an unsaturatedcompound, con-.
taining at least 8 carbon atoms, selected from the group consisting of fatty alcohols, hydroxy fatty acids and hydroxy fatty esters.
2. A sulphation product of an ester of naphthenic acids with an unsaturated fatty alcohol containing at least 8 carbon atoms.
3. A sulphation product of an ester of naphthenic acids with an unsaturated hydroxy fatty acid containing at least 8 carbon atoms.
4. A sulphation product of an ester of naphthenic acids with an unsaturated hydroxy fatty ester containing at least 8 carbon atoms.
5. A sulphation. productof an ester of naphthenic acids with oleyl alcohol.
' 6. A sulphation product of an ester of naphthenic acids with ricinoleic acid.
7. A sulphation product of an ester of naphthenic acids with castor oil.
8. An emulsifying, dispersing and wetting agent comprising essentially a water-soluble salt'of a sulphation product of an ester of naphthenic acids with'an unsaturated compound, containing at least 8 carbon atoms, selected from the group consisting of fatty alcohols, hydroxy fatty acids and hydroxy fatty esters.
' 9. An emulsifying,dispersing and wetting agent comprising essentially a water-soluble salt of sulphated oleyl naphthenate.
' 10. An emulsifying, dispersing and wetting agent comprising essentially a water-solublesalt, of sulphated ricinoleyl naphthenate.
11. An emulsifying, dispersing and wetting agent comprising essentially a water-soluble salt of sulphated naphthenic acids-castor oil ester.
12. An emulsifying, dispersing and wetting agent comprising essentially a water-soluble salt of a sulphation product of an ester of naphthenic acids with an unsaturated fatty alcohol containing at least ,8 carbon atoms.