US3763053A

US3763053A - Alkanolamides of dicarboxylic acid

Info

Publication number: US3763053A
Application number: US00233709A
Authority: US
Inventors: A Bills
Original assignee: Westvaco Corp
Current assignee: Westvaco Corp
Priority date: 1972-03-10
Filing date: 1972-03-10
Publication date: 1973-10-02
Anticipated expiration: 1990-10-02

Abstract

Alkanolamides of this invention are made by condensing a dicarboxylic acid of the following formula:

WHEREIN X AND Y ARE INTEGERS FROM 3 TO 9, X AND Y TOGETHER EQUAL 12, Z is a member of the group consisting of hydrogen and COOM1 with one Z of each moiety, and M and M1 are selected from the group consisting of hydrogen, sodium, potassium, lithium, and mixtures thereof, with either monoethanolamine, diethanolamine or isopropanolamine. The bisalkanolamides, dialkanolamides and monoalkanolamides formed at a ratio of 2:1 alkanolamine:carboxyl moiety are excellent detergents and wetting agents. The bisalkanolamides, dialkanolamides and monoalkanolamides of this invention made at a 1:1 ratio of alkanolamine-to-carboxyl moiety are used as foam, wetting and viscosity boosters. When small amounts of these alkanolamides are added to soaps, the formation of insoluble soaps in hard water is hindered and the resulting insoluble soaps are kept dispersed.

Description

United States Patent 1191 Bills 1 ALKANOLAMIDES OF DICARBOXYLIC ACID [75] Inventor: Alan M. Bills, Summerville, SC.

[73] Assignee: Westvaco Corporation, New York,

[22] Filed: Mar. 10, 1972 [21] Appl. No.: 233,709

[52] U.S. Cl 252/357, 252/527, 252/529, 252/578, 260/404 [51] Int. Cl 801i 17/22 [58] Field of Search 252/527, 546, 529, 252/357; 260/514 K, 557, 404

[56] References Cited UNITED STATES PATENTS 2,337,846 7/1941 Coleman et al 260/557 R 2,744,888 5/1956 Carnes et al 252/117 2,749,361 6/1956 Yale 260/557 R 3,088,967 5/1963 Pare 260/557 R 3,575,883 4/1971 Foley 255/527 Primary Examiner-Leon D. Rosdol Assistant ExaminerEdith L. Rollins Attorney-Ernest B. Lipscomb et a1.

[ ABSTRACT Alkanolamides of this invention are made by condens- Oct. 2, 1973 ing a dicarboxylic acid of the following formula:

wherein at and y are integers from 3 to 9, x and y together equal 12, Z is a member of the group consisting of hydrogen and COOM, with one Z of each moiety, and M and M are selected from the group consisting of hydrogen, sodium, potassium, lithium, and mixtures thereof, with either monoethanolamine, diethanolamine or isopropanolamine. The bisalkanolamides, dialkanolamides and monoalkanolamides formed at a ratio of 2:1 alkanolaminezcarboxyl moiety are excellent detergents and wetting agents. The bisalkanolamides, dialkanolamides and monoalkanolamides of this invention made at a 1:1 ratio of alkanolamine-to-carboxyl moiety are used as foam, wetting and viscosity boosters. When small amounts of these alkanolamides are added to soaps, the formation of insoluble soaps in hard water is hindered and the resulting insoluble soaps are kept dispersed.

5 Claims, No Drawings 1 ALKANOLAMIDES or DICARBOXYLIC ACID BACKGROUND OF THE INVENTION I. Field of the Invention This invention relates to a class of bisalkanolamide, dialkanolamide and monoalkanolamide surface active agents. More particularly, this invention relates to bisalkanolamides, dialkanolamides and monoalkanolamides made from C -dicarbo'xylic acids; bisalkanolamides, dialkanolamides and monoalkanolamides made from blends of C -dicarboxylic acid with other fatty acids; and alkanolamides made from soaps of C dicarboxylic acid blended with other fatty acids and fatty acid alkanolamides.

2. The Prior Art The condensation products of carboxylic acids and either monoethanolamine, diethanolamine or isopropanolamine are generally referred to as alkanolamides. The condensation takes place according to reaction [I]. [l] R-COOH NH CH CH OH R-CoNHCH CH Ol-i H2O monoethano lamine This reaction was discovered by Kritchevsky when diethanolamine and coconut fatty acids were reacted. It was found that if a mole ratio of 1:1 alkanolamine to fatty acid was employed, the product was insoluble in water. However, using a mole ratio of 2:1, alkanolamine to carboxyl moiety, a product quite soluble in water and possessing excellent wetting and detergency properties was produced. It was later determined that the insoluble I21 product was soluble in the presence of another detergent and that it significantly boosted the foaming, foam stability and detergency of the detergent to which it was added.

Although reaction [1] may appear to be straightforward, there are, in fact, two significant side reactions which occur: [2] R-COOH NH -CH CH OH R-COOCH CH NH H O These two reactions, [2] and [3], are due to the bifunctionality of the alkanolamine. It is possible by choosing the correct conditions to minimize reactions [2 and [3] and cause the predominant reaction to be [I]. In general, the lower the temperature consistent with a reasonable rate of amide formation, the less ester is formed. Any ester formed can be considerably reduced by heating the product with an alkali metal alkoxid e, which tends to convert the esters to amides. The presence of esters is undesirable because of their deleterious effect on foaming. If a mechanical mixture of fatty alkanolamide and alkanolamine is formed, it does not possess 'the solubility and surface active properties of the product made by reacting two moles of alkanolamine and one mole of fatty acid. However, by merely heating the mechanical mixture at l20I40C., the properties of the 2:1 ratio of alkanolamide to fatty acid detergent are regained. The optimum detergen'cy in the 2 2:] products requires at least 5 percent alkanolamine soap to remain in the reaction mixture. An example of alkanolamides made from tall oil fatty acids is set forth in U. S. Pat. No. 2,744,888 to Carnes et al.

The applications of fatty acid alkhaolamides are numerous, but the most important are foam boosting and stabilization, viscosity increasing, detergency, emulsification, increased wetting and lime-soap dispersion. The 2:] products (alkanolaminezcarboxyl moiety) are excellent detergents and wetting agents in their own right and are used as such in many products. However, the 1:! products are normally used in conjunction with other detergents as detergency boosters. The addition of only 5 percent of a lzl alkanolamide to an alkyl aryl sulfonate-phosphate formulation boosts its detergency by 33%. Small amounts of alkanolamides added to soaps hinder the formation of insoluble soaps in hard water. Alkanolamides) form excellent oil-in-water emulsions, and are therefore used extensively in cosmetic and pharamaceutical formulations. They also enhance the emulsifying properties of other emulsifiers such as ethylene oxide condensates of 'fatty acids. An important attribute of alkanolamides is their ability to increase the viscosity of other detergent formulations.

The reason for the great use of coconut fatty acids (lauric-myristic) as opposed to oleic types is by no means arbitrary. The fact is that optimum foam boosting properties for alkanolamides are found to be dependent on the number of carbon atoms in the fatty acid chain. Laurie is the most effective and the foam height drops off rapidly as the number of carbon atoms increase in the fatty chain.

It has been found that certain C -dicarboxylic acids may be reacted with alkanolamines to make bisalkanolamides, dialkanolamides and monoalkanolamides having good surface active properties. It is therefore the general object of this invention to provide novel bisalkanolamides, dialkanolamides and monoalkanolamides. It is another object of this invention to provide bisalkanolamides, dialkanolamides and monoalkanolamides from certain C -dicarboxylic acids. Another object of this invention is to provide alkanolamides from C -dicarboxylic acid soaps. Still another object of this invention is to provide novel bisalkanolamides, dialkanolamides and monoalkanolamides for blending with conventional alkanolamides to make detergents.

Other objects, features and advantages of this invention will become apparent from the following detailed description.

SUMMARY OF THE INVENTION There is disclosed C -dicarboxylic acid bisalkanolamides, dialkanolamides and monoalkanolamides compr isir g a fatty acid compound of the following formula:

/oii=ofi CH;(CH:);CH CH-(CHz)y-"COOM CH-C 1 1 Z Z wherein x and y are integers from 3 to 9, x and y together equal 12, Z is a member of the group consisting of hydrogen and COOM with one Z of each moiety, and M and M, are selected from the group consisting of hydrogen, sodium, potassium, lithium, and mixtures thereof, said fatty acid having been reacted with either monoethanolamine, diethanolamine or isopropanolamine. The C -dicarboxylic acid bisalkanolamides, dialkanolamides and monoalkanolamides may be mixed or blended with from about to about 90% by weight of amides of a fatty acid selected from the group consisting of coconut, tallow, tall oil, soya, oleic, safflower and mixtures thereof. The bisalkanolamides formed at a 2:1 mole ratio of alkanolamine to carboxyl moiety have excellent surface active properties, and the bisalkanolamides made at a 1:1 mole ratio (alkanolaminezcarboxyl moiety) are excellent detergent boosters.

DETAILED DESCRIPTION OF THE INVENTION The essence of this invention is the discovery that when a mixture of predominately 5 carboxy-4 hexyl-2 cyclohexene-l-octanoic acid and 6 carboxy-4 hexyl-2 cyclohexene-l-octanoic acid is condensed with ethanolamine, diethanolamine or isopropanolamine, the bisalkanolamides, dialkanolamides and monoalkanolamides formed provide not only the advantages of a conventional alkanolamide, but also provides additional advantages such as, for instance, increased detergency. The mixture of these two isomers is represented by the sasrs istm atwherein x and y are integers from 3 to 9, x and y together equal 12, where Z is a member of the group consisting of hydrogen and COOM with one Z of each moiety, and M and M are hydrogen or are selected from various neutralizing agents. Although the isomers wherein x is 5 and y is 7 form a preponderance of the composition, there are minor amounts of the C dicarboxylic acid where cyclohexene ring varies in position along the carbon chain. For the purpose of this specification, compositions of the general formulation shown above are termed C -dicarboxylic acid soaps," and in the acid form are termed C -dicarboxylic acid ore more simply C -diacid.

The C -dicarboxylic acids used in this invention are produced from linoleic acid of various animal, vegetable and tall oil sources. The C -dicarboxylic acids may be made by reacting linoleic acid with acrylic acid and catalytic amounts of iodine. One such process for making the C,,-dicarboxylic acids for use in this invention is set forth in co-pending application, Ser. No. 159,070 filed July 2, 1971 now US. Pat. No. 3,734,859. When C -dicarboxylic acids are made from tall oil fatty acids according to the process in patent application Ser. No. 159,070, the reaction mixture is approximately 40% C -dicarboxylic acids and 60% oleic acid. The C dicarboxylic acid alkanolamide may also be mixed with other fatty acid amides at from about 5 percent to 90 percent by weight. These amides include in addition to oleic acid those from coconut, tallow, soya, tall oil, safflower and mixtures thereof.

The method of preparing the bisalkanolamides dialkanolamides and monoalkanolamides of this invention comprises, in general, reacting the c -dicarboxylic acid or a mixture of C -dicarboxylic acid and other fatty acid with an alkanolamine from the group consisting of monoethanolamine, diethanolamine or isopropanolamine at a mole ratio of from 1:1 to 2.221 alkanolamine to carboxyl moiety at temperatures sufficiently high to produce the condensation reaction to form the alkanolamide.

A preferred method of producing the bisalkanolamides of this invention is to mix a C -dicarboxylic acid with monoethanolamine in equimolar quantity plus a small amount of excess alkanolamine, i.e., 3% to 10%, and heating this mixture to between l40200C., preferably l50l70C. until the alkanolamide is formed, while removing the water of reaction.

The catalytic effect of sodium hydroxide in the preparation of bisalkanolamides of C ,-dicarboxylic acid from the dialkanolamines is critical, since without it, it was not possible to produce the bisalkanolamide. Sodium hydroxide is added to the condensation reaction in an amount of 0.1 percent to 5 percent by weight of C -dicarboxylic acid and alkanolamine together, preferably 0.25 percent to 1.0 percent.

The alkanolamides of mono-soaps of C dicarboxylic acid are generally either solids or very viscous liquids, but have one attribute not generally afforded by normal alkanolamides, water solubility. Of course, this solubility is due to the soap part of the molecule, but it may be a desirable characteristic in some applications. For example, the use of this material as a self-contained detergent-lime soap dispersant system is one application.

The bisalkanolamides, dialkanolamides and monoalkanolamides of C -dicarboxylic acid find utility as foam boosters, wetting improvers, viscosity increasers and lime soap dispersers. The physical and chemical characteristics of the C -dicarboxylic acid alkanolamides compared to oleic-type and other commercial alkanolamides appear in the Tables.

The C -dicarboxylic acids 1:1 bis-mono and bisdiethanolamides are both viscous liquids; whereas, the corresponding lauric-myristic-types are solids. This property is an advantage in applications where handling of solids is a problem. Since one of the main uses for alkanolamides is in foam boosting, a study of this reaction was made utilizing the Ross-Miles procedure for measuring foam height and foam stability. The data shown gives indications of the foam boosting or lack thereof of the alkanolamides in the presence of as ethoxylated nonyl phenol. The C dicarboxylic acid 1:1 bis-monoethanolamide is better at foam boosting and stabilization than the commercial lauricmyristic monoethanolamide. The Draves wetting test was used to show improvement in wetting of a sulfated myristyl alcohol in a light-duty detergent formulation. The bisalkanolamides from C -dicarboxylic acid and alkanolamides from C -diacid 40%Ioleic acid mixtures gave good results when compared to the oleic-type alkanolamides. The monoethanolamide of the monosodium soap of C,,-dicarboxylic acid gave very good wetting properties. The lime soap disperson index may be the key to using some of these materials in a phosphatefree detergent. The 1:1 bis-monoethanolamide of a mixture C -dicarboxylic acid and oleic acid (4096/6096) has excellent lime-soap dispersing powers.

The following examples are illustrative of the practice of this invention.

EXAMPLE 1 Preparation of Bis monoethanolamide Two commercially available fatty acids and two C dicarboxylic acids were made into their respective bismonoethanolamides and their properties compared. The reaction procedure for producing a 1:1 ratio of alkanolamine-to carboxyl moiety formation consisted of charging a reaction vessel with the fatty acid and an equimolecular quantity of monoethanolamine plus excess. This mixture with continuous agitation, was heated at about l70175C., under a nitrogen purge. The reaction was monitored by measuring the amount of water produced and the acid number of the reaction mixture. The reaction was stopped when the acid number dropped below 5.

Following the same procedure, bismonoethanolamides were prepared at a ratio of 2:1

ties compared. Both 1:1 diethanolamine-to-carboxyl moiety ratio and 2:1 diethanolamine-to carboxyl moiety ratio amides were prepared. The reaction vessel was charged with the fatty acid and proper amounts of diethanolamine plus about 5% excess amine. To the reaction mixture 0.25% by weight of the mixture of solid sodium hydroxide was added to catalyze the reaction. The reaction mixture was continuously stirred while heated at about l70-175C. The rate of reaction remained constant until almost all of the theoretical amount of water had been removed. The resulting product was estimated by IR to be over 75% bisdiethanolamide. There was some ester in the product; however, by aging the material at 60C. for several days, considerable reduction in ester content was achieved with a corresponding increase in bisdiethanolamide. The physical and chemical characteristics of the bis-diethanolamides are given in Table II.

TABLE II.PHYSICAL AND CHEMCIAL cHARAcrERIsTIcs oi BIS-DIETHANOLAMIDES Solubility (10%), degrees Moles, Amide Gard- Water Ethanol Chloroform Benzene Example amine: content, ncr Acid Alkali number Starting material acid Physical state percent color number number 60 25 60 25 60 25 60 fl Czr-(licarboxylic ecid 1:1 Viscous liquid 10 5 D D S S S S S S 10 Czr-diaCid, 10%/oleic 1:1 Liquid 60 10 6.4 61.8 G G S S S S S S acid, 60%. 11 Laurie myristic acid..... 92 2 0.1 10-20 D D S S S S S S 12 Westvaco, 1,480 65 8+ 3.9 60 G G S S S S S S 13 Cn-dicarboxylic acid. 9 6. 0 S S S S S S D D 14 C-zi-diacid. %/oleic 12 7.0 G G S S S S S S acid, 15 Laurie myristic acid..... :1 4 10-14 180-200 S S S S 16 Westvaco, 1,480 B :1 Liquid. 64 7+ 2.8 149.8 G S S S S S S NOTES: n S=soluble, I=insoluble, D=dispersible, G=gel; Distilled, disproportionated tall oil fatty acid (Cm).

EXAMPLE 3 monoethanolamine to carboxyl moiety. Physical and chemical characteristics of the bis-monoethanolamides are shown in Table I.

The amide content of the alkanolamides is difficult to determine chemically due to the presence of amideesters and ester-amines. However, IR spectrophotometry was used with some success with the lauric-type amides. A pure smaple of C -dicarboxylic acid, bismonoethanolamide was isolated by column chromatography. Using this material as a standard, an estimate of the amide content of a C -dicarboxylic acid, and mixture of C -diacid (40 percent) and oleic acid (60 percent) alkanolamide was made. This was about percent.

Preparation of Alkanolamides of Mono-soaps of C ,-Dicarboxylic Acid TABLE I.PHYSICAL AND CHEMICAL Cfi'A'RACTERISTICS OF BIs-MONO'ETFIANOLAMiDEs Solubility (10%), degrees Moles. Amide Gard- Water Ethanol chloroform Benzene Example amine: content, ner Acid Alkali number Starting material acid Physical state percent color number number 25 60 25 60 25 60 25 60 1 Cm-dicarhoxylic acld.... 1:1 Viscous liquid... 78 10+ 6.7 19.0 I I S S S S I I 2 CzrdiCtllbOXyliC acid, 1:1 Soft solid 83 14 4.0 14.0 I I S S S S S S 40%l0leic acid, 60%. 3 Lauric-myristic acid..... 1:1 id 92 6 5-12 10-20 I I I S D S D S 4. Westvaco, 1,480 c 1:1 Soft solid... 92 12+ 2. 1 12. 5 I I S S S S S S 5. Czi-cliearboxylic acid. 2:1 Liq 7 10+ 7.0 63.8 I D S S S S I D 6 Car-diearboxylic acid, 2:1 S01 79 12 2.7 177.0 D D S S S S S D 40%/oleie acid, 60%. 7 Lauric-myristic acid... 2:1 Paste 65 4 10-14 -200 S S S S D D D I) 8... Westvaco, 1,480 2:1 Soft solid 84 12 2.3 150. 5 I I S S S S S S NOTES: S=soluble, I=insoluble, D=dispersible; Distilled, disproportionated tall oil fatty acid (C15).

EXAMPLE 2 Preparation of Bis-diethanolamides As in Example 1, two commercially available fatty acids and two C -dicarboxylic acids were made into their respective bis-diethanolamides and their propertheoretical amount of water had been removed (water added with caustic plus water from salt formation plus water from alkanol amide formation) the reaction was terminated. The products were generally soluble or dispersible in water. The physical and chemical characteristics are given in Table 111.

EXAMPLE 4 l4 C -Diacid 40%] Oleic Acid 60% Mixture I5 Lauric acid 15 I6 Westvaco I480 l5 LIME SOAP DISPERSION INDEX FOR AL- KANOLAMIDE SOAPS I7 MEA c -Diacid Monosodium Soap I5 18 DEA C -Diacid Monopotassiurn Soap 100 I9 MEA C -Diacid 40%] Oleic Acid 60% Mixture Sodium Soap EXAMPLE 6 Wetting time for the bisalkanolamides determined by the standard test method of the American Association of Textile Chemists and Colorists, AATCC l7-l952. The principle of this method is the measurement of the TABLE III.PIIYSICAL AND CHEMICAL CHARACTERISTICS OF ALKANOLAMIDE-SOAPS Cir-DICAREOXYLIC ACIDS Solubility (10%) degrees Water Ethanol chloroform Benzene Example Physical Gardner Acid Alkali number Amide soap state color number number 25 60 25 60 25 60 25 60 17 Monoethanolamide of cz dicarboxylic acid Hard clear solid. 8 5.0 145.0 S S S S I I I I monosodium soap. I 18 Diethanolamide of Czi-dicarboxylic acid Very viscous 9 S S S S S S D D monopotassium soap. 'qui I E6153 fv Solubility (10%) degrees Water Ethanol Chloroform Benzene Example Physical Gardner Acid Alkali number Amide soap state color number number 25 60 25 60 25 60 25 60 19 Monoethanolamide oi C dicarboxylic acid, Solid 5 S S I I I I I I 40% oleic acid 60%, monosodium soap.

EXAMPLE 5 This example illustrates the ability of the bisalkanolamides and alkanolamide soaps to disperse the insoluble calcium or magnesium soap of oleic acid. The procedure used to determine this value was the method of Borghetty and Bergman which is:

Lime Soap Disposing Powder grams of dispersing agent to disperse soap X l00/weight of sodium oleate The results are given in Table V for the bisalkanolamides and the alkanolamide soaps from Examples 1-4.

time required to wet a standard cotton skein at a particular temperature and a standard concentration of wetting agent. The weighed cotton skein is immersed in the wetting solution in a graduate cylinder and the time required to cause the cotton stirrup connecting the skein to the weight to relax is recorded as the sinking time. The temperatures employed in this test were 25C. and 50C. and the concentration of wetting agent in a standard light-duty detergent formulation was 0.1 and 0.25%. The cotton skeins were 5.00 grams and the hooks used were fabricated out of No. 10 copper wire and were made to weigh exactly 3.00 grams each. The results for the bisalkanolamides are given in Table VI.

The light duty detergent formulation from which the wetting solutions were prepared was as follows.

2.5 grams amide 12.5 grams sodium tetradecyl sulfate grams isopropyl alcohol 27.5 grams water 'The 0.1 and 0.25% figures represent the sum of the alkanolamide plus the sodium tetradecyl sulfate.

Foam height and stability of the bisalkanolamides of the invention were compared to the alkanolamides from commercial fatty acids according to the Ross- Miles test. The tests were run on the bisalkanolamides, bis-dialkanolamides and alkanolamide soaps made in Examples [-4. The test was carried out using a 20:80 mixture (amidezsurfactant) with an exthoxylated nonyl phenol (lgepal C030). The results for both the acids and soaps are also given in Table VI.

TABLE vi Foam height and Wetting time, seconds stability, 80% igepal 25 C. 50 C. CO30/20% additive Example number Fatty acid base 0.1% 0. 25% 0.1% 0.25% min. min. 1 Cn-diacid 100 17 180 14. 5 12. 3 12. 3 l. Cm-diacid 40%/oleic 60%-.." 200 28 181 18 12.5 7. 0 3..- Louric-myristic Ins. Ins. 16 3. 5 8.0 3. 8 4.. Westvaeo, 1, 480 159 36 71 20. 0 8.5 4. 0 5 Cn-diacid 117 9 130 7 9.5 9.5 0.. Cn-diacid, 10%/oleic, 60%"... 150 22 115 16 13. 1 13.0 7 Lnuric-myristic Ins. Ins. 20 5 15.0 15.0 8.. Westvaco, 1,480 154 38 87 25 5. 2 3. 4 l Czi-diaeid 348 30 189 23 13. 8 13. 0 10- Czi-dlacid, 40%/oleic, 60% 365 32 241 28 13. 0 13.0 11. Laurie acid 4 10 2 13. 9 13.9 1;. Westvaco, 1,480 '2. 373 43 178 29 12. 5 12. 5 13. .:1- acid 13. 0 13. 0 14. Csr-diucid, 10%/oleic, 60%. 420 30 420 25 14. 2 14. 2 15. Laurie acid 24 5 24 3 15.0 15.0 16.... Wcstvueo, 1, 480 106 07 44 31 13. 5 13. 5 Control. Sodium tctrndocy 420+ 30 420+ 28 17 EA. Czi-diacid monosodiuni 30 11 27 7 13.8 13.8 18 1) EA. (:i-diacid monopotassium Sou 115 10 00 0 15. 4 15. 4 10 MEA. Czi-diacid, 10%/oleic, 60% mixture sodium soap... 118 111 15 NOTES: e Distilled, disproportionntcd tall oil fatty acid (Cm); Ins.=Insoluble.

While the invention has been described and illustrated herein by references to various specific materials, procedures and examples, it is understood that the invention is not restricted to the particular materials, combinations of materials, and procedures selected for that purpose. Numerous variations of such details can be employed, as will be appreciated by those skilled in the art.

Having thus described the invention, what is claimed is:

1. An alkanolamide consisting essentially of the condensation product resulting from heating together at temperatures between l40C-200C,

a. an alkanolamine selected from the group consisting of monoethanolamine, diethanolamine and isopropanolamine, b. with a mixture of dicarboxylic acids having the formula:

(DI-1:011 0 ll cimcm cu cmcnm- -Oll CH-ClI wherein x and y are integers from 3 to 9, x and y together equal 12, where one Z is a hydrogen (H) and the other Z is a carboxylic acid group (COOH) said ratio of alkanolamine to carboxyl group being 2:1 to I11.

2. The bisalkanolamide according to claim 1 wherein the mole ratio of alkanolamine to dicarboxylic acid is 3. The product of claim 1 wherein the alkanolamine is monoethanolamine and the temperature is between 150 and 170C.

4. The product of claim 1 wherein said alkanolamine is diethanolamine, said temperature is between 150 and 170C, and sodium hydroxide is present in an amount of between 0.1% and 5.0% by weight of said dicarboxylic acid and amine.

5. A composition consisting essentially of:

A. A bisalkanolamide consisting essentially of the condensation product resulting from heating together at temperatures between 140C-200C, an alkanolamine selected from the group consisting of monoethanolamine, diethanolamine, and isopropanolamine, with a mixture of dicarboxylic acid having the formula,

wherein x and y are integers from 3 to 9, x and y together equal l2, where one Z is a hydrogen and the other Z is a carboxylic acid group, said ratio of alkanolamine to carboxyl group being 2:1 to 1:1; and

B. An amide of a fatty acid selected from the group consisting of coconut, tallow, tall oil, soya, oleic, safflower and mixtures thereof, said composition comprising from about 5 to by weight (A) and from 10% to by weight of (B).

Claims

2. The bisalkanolamide according to claim 1 wherein the mole ratio of alkanolamine to dicarboxylic acid is 1:1.
3. The product of claim 1 wherein the alkanolamine is monoethanolamine and the temperature is between 150* and 170*C.
4. The product of claim 1 wherein said alkanolamine is diethanolamine, said temperature is between 150* and 170*C., and sodium hydroxide is present in an amount of between 0.1% and 5.0% by weight of said dicarboxylic acid and amine.
5. A composition consisting essentially of: A. A bisalkanolamide consisting essentially of the condensation product resulting from heating together at temperatures between 140*C-200*C, an alkanolamine selected from the group consisting of monoethanolamine, diethanolamine, and isopropanolamine, with a mixture of dicarboxylic acid having the formula,