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Publication numberUS2317555 A
Publication typeGrant
Publication dateApr 27, 1943
Filing dateNov 15, 1941
Priority dateNov 15, 1941
Publication numberUS 2317555 A, US 2317555A, US-A-2317555, US2317555 A, US2317555A
InventorsRobinette Hillary
Original AssigneeCommercial Solvents Corp
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Surface active agent
US 2317555 A
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Description  (OCR text may contain errors)

Patented Apr. 27, 1943 STATES amass TENT SURFACE acrrva AGENT Hillary Robinette, Terre Haute, Ind, asslgnorto Commercial Solvents Corporation, Terre Haute, .Ind., a corporation of Maryland No Drawing.

4 Claims,

wherein It represents an alkyl group having at least fivecarbon atoms.

As specific examples of the substituted 1.3- dioxanes which are included by the above generic formula,, there may be mentioned -amino -2- (3- pentyl) '-5-hydroxymethyl-1,3-dioxane, 5-amino- '2-hexyl-5-hydroxymethyl-1,3-dioxane, 5-amino- 2-(3-heptyl) -5-hydroxymethyl-1,3-dioxane, 5- amino-2-hendecyl -5-hydroxymethyl-1,3-dioxane,

- 5-amino-2-octyl-5 hydroxymethyl-1,3-dioxane,,

and the like.

' In numerous industries there exists a need for certain types of chemical compounds ordinarily employed in small quantities, to secure an efiect which is principally the result of a wetting ac- Specifically, these compounds" tion, such as the effect obtained by the presence of a surface active agent at a water oil interface. For example, in the textile and leather-treating industries, there are many situations where wetting or detergent action is vhighly desirable; as aresult, many different agents have been proposed to reduce surface tension and promote wetting". The materials that have been employed in the past, however, although satisfactory in some respects, have not met with unqualified success in all cases.

The ordinary soaps, although their surface active properties have long been recognized, are deficient in many respects when employed in the field'of detergent and wetting agents. For example, although soaps act emciently as detergents in weakly alkaline solutions, they are of no value for this purpose in acid solutions since under such circumstances the free fatty acids,

which is insoluble in water, is liberated. In'

strongly alkaline solutions, on the other hand, ordinary soaps becomeinsoluble and are salted out of solution. In addition, in the presence of Application November 15, 1941, I Serial No. 419,317

solutions containing calcium or magnesium salts, such as ordinary hard water, the fatty acid present in the soap is precipitated as a calcium or magnesium soap, such soaps being insoluble, sticky materials, which, rather than having any detergent action, are regarded as undesirable impurities in solutions employed in the textile and related industries.

In an effort to furnish materials to such industries, free from the undesirable properties of ordinary soaps, there have been developed as detergent and wetting agents, products obtained by the sulfonation of certain fatty acids occurring in oils and fats. Such fatty acids are characterized by containing unsaturated linkages and/or hydroxyl groups in the molecule. On sulfonating such acids, products are obtained which contain sulfuric acid ester groups in the molecule, and of course carboxylic acid groups are attached to the terminal carbon atoms. The products, however, in general possess weaker wetting and detergent properties than soaps. Such products are also relatively unstable and are capable of being decomposed by hydrolysis.

Other proposed wetting agents comprise the semiand completely-esterified products resulting from the esterification of a higher alcohol with an unsaturated polybasic acid. After the unsaturated esterlfied acid is produced, it is converted into a more soluble form,- ordinarily by treatment with sodium bisulfite to yield'the corresponding sulfo derivative of the esterified polybasic acid. While such materials have met with a considerable degree of success in various in- 5 35 dustries where the need for surface-active materials exists, they are not without certain defects. Obviously surface-active agents of this type are not stable to alkali and in some instances, especially in the textile field, much difficulty has been experienced with the tendency of the textile treating baths containing such materials, to foam.

I have now discovered that aminodioxanes of the class included by the above structural formula serve as highly satisfactory wetting agents, particularly where prior wetting and detergent agents, especially of the type mentioned above, are of littleor no value. For example, the wetting agents of the present invention are not decomposed either by hard waters, or solutions containing appreciable quantities of alkali. My new wetting agents possess the further advantage in that aqueous solutions thereof do not foam. In addition, these materials. which are water-white liquids, are soluble in most of the common organic solvents.

In general, the quantity of the new wetting agents which may be employed will be found to vary with the type of wetting operation under consideration, as well as with the material to be wetted. For most purposes, however, I have found that these wetting agents may be utilized in amounts of from about 0.15 to 0.60 per cent by weight of the treating bath. In this connec tion, I have found that in many cases it may be desirable to employ a solubilizing material with the Wetting agents of the present invention. In such instances, the quantity of wetting agent employed may be reduced, depending of course upon'the quantity and type of solubilizing agent employed. Suitable solubilizing materials which may be utilized in combination with my wetting agents, are sulfonated castor oil, sulfonated pctroleum oils, sulfonated alkyl aromatic compounds, sulfated esters, sulfated ether-alcohols, sulfonated alkyl diphenyls, soaps and the like.

The wetting power of certain of the aminodioxanes of the present invention is demonstrated by the data appearing in the table below, and was measured by the method of Draves and Clarkson (Am. Assoc... Textile Colorists and Chemists Year Book, v01. 17, pp. 216-222 (1940)), which determines the sinking time required for a gram skein of unboiled 2-ply' cotton yarn in varying concentrations of aqueous solutions of the aminodioxanes at a temperature of 30 C.

Table rams of 'q k ammo in mg Ompmmd dioxane L time per liter 5-amino-2- (3-amy1)-5-hydroi;ymethyl-l 3- Seconds dioxane 1 6 27 5-amino-2-hexyl-5-hydro met ,3-

dioxane 3 1. 5 150 5-llXIllll0 -2- (3-heptyl) 5 hydroxymethyl- 1.3-dioxanc 2 3 l {I 1 Instantaneous.

The wetting agents of the present invention may be prepared in accordance with any of several suitable procedures. I prefer, however, to produce such materials by means of the process described in U. S. Patent No. 2,247,256 granted June 24, 1941, to Murray Senkus. In a procedure of this character, the corresponding nitrodioxane is subjected to high-pressure hydrogenation in the presence 'of a. nickel catalyst and a suitable solvent such as methanol, at a temperature in the neighborhood of -30 C. The starting materials in this process are conveniently prepared by condensing tris(hydroxymethyl) -nitromethane with any of a number of suitable aldehydes, such as hexanahheptanal, 2-ethylhexanal, dodecanal, and the like. This condensation reaction is carried out by heating tris(hydroxymethyl)nitromethane in the presence of the desired a1dehyde and a small quantity of an acid catalyst; and, if desired, in the presence of an organic liquid, such as benzene or toluene, which is capable of removing the water produced during the reaction in the form of a constant boiling mixture.

With reference to the compounds covered by certain of the species claims herein, these materials, .i. e., 5-amino-2-hexyl-5-hydroxymethyl- 1,3 -dioxane and 5-amino-2(3-heptyl) -5-hydroxymethyl-1,3-dioxane, maybe synthesized by first of a suitable nickel catalyst, such as Raney.


It is understood that applicant does not claim the amino dioxanes per se disclosed and referred to herein, but instead, claims merely a new and novel use of said compounds.

As previously stated, the wetting agents of' the present invention may be used alone or in combination with certain solubilizing agents, or other detergents, for cleansing and securing vegetable and animal fibers when removing fatty or oily materials therefrom. They may also be used as penetrants in flax-retting baths. The

penetrating power of these new compositions may be utilized with advantage when said compositions are added to baths containing starchy ferments which are employed for removingsizing from textile materials. These products function as useful wetting, cleansing and penetrating agents in bleaching liquors, such as those used in the kier boiling of cotton goods, and may be added to the lye liquors used for mercerizing cotton goods. They can also be used to assist in twist setting of yarn and in processes of stripping colors. Such compounds may also be used as assistants in processes of stripping dyes from dyed textile material.

A second class of uses of these new surface- ,active agents is as assistants in the application of dyestuffs. They may be used as dye levelingagents due to their wetting and penetrating properties in neutral or alkaline dyeing baths, and are capable of facilitating dyeing with developed dyes, the dyeing of acetate fibers with insoluble. dyes, the dyeing of animal fibers with vat-dyes, the dyeing of various synthetic fibers, and. the dyeing of leather.

It will readily be seen from the foreging discussion that by means of the present invention a large group .of new. surface-active materials has been made available, and that suchagents are adapted for use in numerous industrial processes which require surface-active substances. It will also be apparent to those skilled in the art that many widely different embodiments of the present invention exist, and that such embodiments may be utilized without departing from the scope of said invention.

My invention now having been described, what I claim is:

1. In the process for the wet treatment of organic fibrous materials in an aqueous bath, the improvement which comprises incorporating in the bath in an amount to change its surface wherein R represents'an alkyl group having at.

least five carbon atoms.

2. In the process for the wet treatment of organic fibrous materials in an aqueous bath, the step which comprises incorporating in the bath in amounts of from about 0.15 to 0.60 per cent by weight of the final solution, an aminodloxane having the formula:

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4384872 *Mar 5, 1979May 24, 1983Institute Of Gas TechnologyStabilized gasoline-alcohol fuel compositions
US5482965 *Sep 3, 1993Jan 9, 1996Rajadhyaksha; Vithal J.Compositions and method comprising aminoalcohol derivatives as membrane penetration enhancers for physiological active agents
U.S. Classification516/67, 549/371
International ClassificationC07D319/06, C11D1/58
Cooperative ClassificationC07D319/06, C11D1/58
European ClassificationC11D1/58, C07D319/06