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Publication numberUS1981792 A
Publication typeGrant
Publication dateNov 20, 1934
Filing dateJun 17, 1933
Publication numberUS 1981792 A, US 1981792A, US-A-1981792, US1981792 A, US1981792A
InventorsJohn W. Orelup
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Sulphated condensation products of
US 1981792 A
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Description  (OCR text may contain errors)

PATENT OFFICE SULPHATED CONDENSATION PRODUCTS OF l lill'a.l".l.Y ACIDS AND MONOETHANOLAM- John W. Orelup, Summit, N. J.

No Drawing.

15 Claims;

My present invention relates to improvements in wetting, dispersing and emulsifying agents and more particularly to the sulphonated condensation products of certain fatty acids and the mono- 5 alkyl amines, as for example monoethanol amines. While it has been proposed to condense certain of the fatty acids or esters thereof with various amines, the proper acids or mixtures thereof have not been condensed with a proper amine. In

many cases the condensation products so obtained have not been treated with sulphuric acid to form compounds therewith. In all casesthe proposed products have been practically worthless. The following table gives results obtained by observing the sinking time of a piece of wool serge 4 x 4 in a solution of one gram of the wetting agent per litre of tap water of average hardness. The wetting agents were all made by condensing the acid mixture indicated with monoethanolamine followed by treatment with sulphuric acid as described in detail below.

' Sinking time at 26 C.

Sulphuric acid treated condensation product formed from:

First fraction composed of 85% C10 acid 64 sec. Second fraction composed of 64% C12 acid -1 33 sec. Third fraction composed of 87% Ca acid 2'7 sec. Fourth fraction composed of 89% C14 acid 35 sec. Fifth fraction composed of 90% Cm 35 acid 90 sec. Pure palmitic acid (C16 acid) 1320 sec. 'Pure stearic acid (Cm acid) f 600 sec. Methyl ester of palmitic acid 2400 sec. In concentration of 5 grams per liter: 40 Pure palmitic acid 135 sec. Methyl ester of palmitic' acid 275. sec.

Without wetting agents 24 hours.

These acids from which the wetting agents were derived were obtained by fractionating the cocoanut fatty acids containing acids from Ca to C18, i. e. capronic, caproic, capryllic, lauric, myristic, palmitic, stearic by .distillation. It will be seen that the wetting activity reaches a maximum between C12 and C14 acids. Cu; is almost inactive and Cs on the other side is less active than C12 or C14. Because of the predominance of the C12 and C14. acids in cocoanut oil very good results are obtained by using the fatty acids naturally occurringin cocoanut oil or other nut oils of similar composition such as palm kernel oil. In fact, mixtures of several of these fatty acids, such as the mixture of acids in the proportions in which they occur in cocoanut oil and palm nut oil, seem to yield better results than Application June 17, 1933, Serial No. 676,324

are obtained with the C12 or C14 acids alone.

water soluble as entering into the water layer at the surface or interface of the material to be wetted. Now the wetting agent will be most eflicient, other factors being equal, when the fatty soluble chain and the water soluble chain will be balanced or of equal strength. For instance, if the oil soluble function is much stronger than the water soluble, the molecule will tend to be withdrawn mostly into the oil layer and poorer wetting power will result. If, on the other hand,

the water soluble chain surpasses in power the.

oil soluble chain, a tendency for the withdrawal of the molecule into the water results, again with loss of Wetting power. Thus applying this reasoning to the above table, it may be considered that the C12 and C14 groups are the best balanced of the acids given. My theory finds further confirmation in the action of cbmpounds in which the polar activity is increased by the addition of more hydroxyl groups, as by using diethanolamine in the sulphonation product instead of the mono compound. The sinking power is poorer, being of the order of 171 seconds in the concentration of 1 gram per litre. By increasing these groups still further by using triethanolamine the sinking time is raised to 480 seconds.

In order that my invention may be fully understood, I give the following illustrative example using the naturally occurring cocoanut fatty acids:

210 pounds of cocoanut fatty acids having an average molecular weight of 210 is heated with 67 pounds of monoethanolamine for a fewhours in a still until the acid number determined in alcohol sinks to below 5, the water evolved being allowed to escape. The distillate of water and excess 'monoethanolamine amounts to about 19 pounds. The mass on cooling sets to a pale yellow wax-like substance having a solidification point of 60-65" C., and may be sulphonated directly. This product is slightly soluble in water.

This product may be subjected to the action of sulphuric acid in the following manner:

To 100 pounds of sulphuric acid monohydrate pletely homogeneous, tests are made to determine the water solubility. -As soon as the solubility is complete, the mass is mixed with '75 pounds of ice and neutralized while cooling with suflioient 50% caustic soda to bring the whole to a neutral reaction to litmus. The excess sulphuric acid may also be separated by slight dilution or salted out.

This treatment results, as nearly as can beascertained, in the formation of a predominant quantity of the sulphuric esters in which the sulphur atom is joined to the compound by an oxygen linkage and possibly of some slight quantities of true sulphonated compounds in which the sulphur is attached to the carbon atoms. To the type of reaction with sulphuric acid exemplified by said treatment I apply herein the term sulphation.

The amount of sulphuric acid used in the sulphonation is not critical, except that a large excess, as for example double the amount specified, is detrimental. Furthermore, while the temperature may vary within limits, it should not exceed C. More active sulphonating agents may be used as desired, such as chlor-sulphonic, ethionic acid, oleum, etc. However, I have found that the ordinary sulphuric acid monohydrate is sufliciently active for the purpose. In the condensation products described there is only one hydroxyl group.

Contrary to the sulphonated fatty alcohol series, it has been found that the saturated fatty acids give more active compounds with ethanolamine followed by sulphation than the unsaturated. Inert solvents may also be used in the treatment as, for example, trichlorethylene, carbon tetrachloride, etc., but it has been my experience that the advantage so gained does not usually warrant the expense entailed by the use of solvents.

The sulphated products of my invention are an almost white, thick paste, having remarkable detergent and emulsifying properties. These products when used in the dye bath even in very high dilutions give thorough and even dyeing and an excellent feel to the goods. The product is fast to lime, disperses lime soaps and is fast to acid and alkali. It may be incorporated with soap as a soap assistant or it may be used as an emulsifying agent in greases, creams and cosmetics, in securing, as a penetrating agent, in the tanning industry to accelerate tanning, deoiling, dehairing, etc. It may also be used with insecticides to increase their covering power in aqueous form and in such capacity it is termed an insecticide promoter. The product may be dried in a vacuum and reduced to a fine white powder.

In lieu of monoethanolamine, the monopropan01 amines and monobutyl amines may be used.

I claim:

1. As new wetting, dispersing and emulsifying agents, the sulphated product of the condensation reaction of the fatty acids containing a substantial quantity of the C12 and C14 acids withmonoethanolamine.

2. As new wetting, dispersing and emulsifying agents, the sulphated product of the condensation reaction of the naturally occurring fatty acids in cocoanut oil, with monoethanolamine.

3. The new products according to claim 1 being the condensation of a single molecule of fatty acid, a single molecule of amine and a single molecule of sulphuric acid.

4. The new products according to claim 2 being the condensation of a single molecule of fatty acid, a single molecule of amine and a single molecule of sulphuric acid.

5. As new wetting, dispersing and emulsifying agents, the sulphated condensation of products of equi-molar quantities of the naturally occurring fattyacids in cocoanut oil and monoethanolamine. 6. The method of making wetting, dispersing and emulsifying agents which consists in condensing fatty acids containing a substantial quantity of the C12 and C14 acids with monoethanolamine and sulphating the condensation product formed.

7. The method of making wetting, dispersing and emulsifying agents which consists in condensing fatty acids containing a substantial quantity of the C12 and C14 acids with monoethanolamine and sulphating the condensation product formed.

8. In the manufacture of wetting, dispersing and emulsifying agents, the steps of condensing fatty acids containing a substantial quantity of the C12 and C14 acids with monoethanolamine followed by sulphation in which the condensation product is treated with a substantially equal quantity by weight of sulphuric acid mono-hydrate until the mass is homogeneous and water soluble.

9. The method according to the preceding claim in which the temperature of sulphation is maintained at from 30 to 35 C.

10. As new wetting, dispersing, and emulsifying agents, the sulphated condensation products of fatty acids and monoethanolamine in which the respective dissolving powers of the polar and nonpolar components are substantially the same magnitude.

11. As new wetting, dispersing and emulsifying agents, the sulphation products of an acid amide formed by condensing monoethanolamine with a mixture of fatty acids between C10 and C18- 12. The method of making wetting, dispersing and emulsifying agents which consists in condensing fatty acids containing a substantial quantity of the C12 and C14 acids with monoethanolamine by heating such compounds together until the acid number sinks to below 5, and sulphating the condensation product formed.

13. The method of makingwetting, dispersing and emulsifying agents which consists in condensing fatty acids containing a substantial quantity of the acids having from 12 to 14 (inclusive) carbon atoms with monoethanolamine by heating said compounds together until the water formed by the reaction is substantially driven off and sulphating the condensation product formed.

14. The method of making wetting, dispersing 15. The method of making wetting,dispersing and emulsifying agents which consists in condensing fatty acids containing a substantial quantity of the acids having from 12 to 14 (inclusive) carbon atoms with monoethanolamine by heating said compounds together until the I acid number, as determined in alcohol, sinks to below 5 while allowing the water evolved to'

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2545357 *Jun 4, 1946Mar 13, 1951American Cyanamid CoDetergent composition and method of preparing same
US2581677 *Nov 18, 1948Jan 8, 1952 Phosphate detergent composition in
US2843550 *Mar 2, 1954Jul 15, 1958California Research CorpSynthetic detergent compositions
US4116986 *May 6, 1977Sep 26, 1978The United States Of America As Represented By The Secretary Of AgricultureProcess for sulfating fatty alkanolamides
US4252665 *Jun 13, 1979Feb 24, 1981Monsanto CompanyDisinfectant cleaning compositions
EP0780367A2Dec 10, 1996Jun 25, 1997Henkel Kommanditgesellschaft auf AktienAnionic detergent mixture
Classifications
U.S. Classification554/44, 516/DIG.500, 554/49, 516/59, 8/94.21
Cooperative ClassificationY10S516/05, C07C309/17