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Publication numberUS2609381 A
Publication typeGrant
Publication dateSep 2, 1952
Filing dateOct 5, 1949
Priority dateOct 5, 1949
Publication numberUS 2609381 A, US 2609381A, US-A-2609381, US2609381 A, US2609381A
InventorsClary Stanley T, Goldstein Herman B
Original AssigneeSun Chemical Corp
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Amido-amide derivatives of dibasic acids and processes of preparing the same
US 2609381 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

Patented Sept. 2, 1952 ACIDS AND PROCESSES THE SAME OF PREPARING Herman B. Goldstein, Cranston, and Stanley T. Clary, Coventry, It. I., assignors to Sun Chemical Corporation, Long Island City, N. Y., a corporation of Delaware No Drawing. Application October 5, 1949, Serial No. 119,756

14 Claims. 1

The present invention relates to new organic compounds which are valuable as assistants in the treatment and finishing of textile materials.

One object of the present invention is to provide new water dispersible organic compounds useful for the treatment "of textile materials "which, upon such treatment, impart a highly improved hand and enhanced texture thereto.

Another object fof the presentinvention is to provide new water dispersible organic compounds which are substantive to textile-materials and which are highly resistant to ordinary laundering and dry' cleaning methods afterapplication thereto, therebyimparting a relatively permanent finish to suchtreated textiles.

Another'object of the present invention is to provide new-water dispersible textile finishing agents which do not cause discoloration nor yellowing of textile materials treated therewith, Whichare effective over long periods of time and under all the ordinary operations and conditionsto which such textiles are subject, and which do not efi'ect any color change in the shade of dyed fabricsgnorwhichdeleteriously affect the light fastness of dyestiifisi Otherobjects of the present invention will be apparent from the following description and appended claims.

It has been-'f'ound-jtha t the above objects may be accomplished and-Ithat organic compounds having the properties and characteristics described thereinmay be prepared by reacting a high molecular weight aliphatic carboxylic acid, or derivativesthere'of, such as the esters or halides thereof, with a polyamine to form an amide amine of such acid, and thereafter reacting the resultant amido amine with a dibasic acid, or a derivative thereof, such as the anhydride, esters -or acyl halides thereof, in such manner that a disubstituted derivative of the dibasic acid is formed.- I

The organic compounds formed according to the process of the present invention may be considered to be disubstituted amido-amide derivatives of dibasic acids. Similarly, these products may also be considered to be acyl amides of a dibasic acid and high molecular weight aliphatic carboxylic'acids. I 7

The high molecularweight aliphatic carboxylic acidsemployed in preparing the above mentioned amido amines are those containing at least six carbon atoms in the aliphatic chain, as for example, caproic acid, caprylic acid and capric acid, and preferably those containing at least twelve carbon atoms in the'molecule, Among those acids 2 which are preferred for use in the present invention are the higher saturated fatty acids such as lauric acid, myristic acid, palmytic acid, stearic acid, animal and vegetable oil saturated fatty acid compositions such as coconutfatty acids, and hydrogenated fatty acid compositions,

' such as from hydrogenated fish oils, hydrogenated cotton seed oil, hydrogenated soy bean oil and hydrogenated peanut oil. The higher unsaturated fatty acids as, for example, oleic acid, palmitoleic acid, linoleic acid, linolenic acid and eleostearic acid, may also be employed in preparing the compounds of the present invention. However, the use of such acids is notpreferred since the end product, that is, the softener compound, displays a tendency toward slight. discoloration due to the unsaturation in the finished product.

The polyamines which are reacted with the above mentioned acids to provide the amido amines which may be subsequently reacted with a dibasic acid to provide the new organic compounds of the invention, comprise those polyamines containing at least two amino groups of the primary or of thesecondary type,and which may contain one or more aliphatic residues in the molecule. Examples of such polyamines include the diamines such as ethylene diamine, trimethylene diamine, tetramethylene diamine, pentamethylene diamine, and hexamethylene diamine; the polyethylenejpolyamines such as diethylenetriamine, triethylene tetramine, tetraethylene pentamine, etch; substituted diamines such as ethyl ethylene diamine, hydroxyethyl ethylene diamine, N-N'dihydroxyethyl ethylene diamine, N-ethyl N'- aminoethyl ethylene diamine; and such other polyamines as diamineethyl ether and diaminoethyl thioether.

Polyamines of the type exemplified above may be reacted with any of 'thepreviously mentioned aliphatic carboxylic acids to provide an amido,

acid, adipic acid, pimelic acid,- suberic acid and 'sebacic acid; the unsaturated aliphatic dicarboxylic acids such as maleic and fumaric acids; cyclic aliphatic dicarboxylic acids such as 1-4. cyclohexane dicarboxylic acid; and aromatic and alkyl aromatic dicarboxylic acids such as phthalic acid, isophthalic acid, homophthalic acid, and uvitic acid. Other dibasic acids, substituted or interrupted in their structure by hydroxyl, ester, ether and amino groups, or by halogen, oxygen and sulfur atoms may also be employed in the present invention- Some such acids are malic acid, tartronic acid, tartaric acid, l chlorophthalic acid, DL bromobutanedioic acid, aspartic acid, diglycolic acid, and dithioglycolic acid. The anhydrides, esters and acyl halides oi the above mentioned dibasic acids may also be employed in carrying out the invention.

The compounds obtained in accordance with the procedures hereinafter outlined and with the materials above set forth may be represented by the following general formula:

i) R; R3

In the above formula R1 and R7 represent an aliphatic chain containing five or more carbon atoms. Furthermore R1 and R7 may be identical or they may be different, depending upon whether the radicals represented by El and R1 are derived from the same acid or from diiferent acids.

R2, R3, R5 and Rs may represent hydrogen, a lower alkyl radical, or a lower hydroxyalkyl radical, the various substituents corresponding to the terminal substituents occurring in the particular polyamine employed.

Re and R5 may further represent an acyl residue of an aliphatic carboxylic acid. The particular compounds in which R3 and R5 have such representation occur, for example, in an amide amine in which the polyamine has been so reacted with an aliphatic carboxylic acid that both terminal amino groups contain an acyl radical and in which at least one of the acyl substituted. amino groups contains a free hydro-gen atom.

Depending upon the particular polyamine employed in preparing the amide amine, G in the above formula may be a secondary amino group, a simple lower alkyl or lower alkylol substituted amino group, oxygen or sulfur.

The letters a, b, c, d, e and ,1 represent integers, a and 0 representing integers from 0 to 6; and b, d, e and 1 representing integers from 1to6.

That portion of the above general formula represented by X is a dicarboxylic acid residue in which R4 may represent an aliphatic group, a cyclo aliphatic group, an aromatic group or an alkyl aromatic group. R4 may also represent any of the said groups substituted within their structure by halogen, oxygen, and sulfur atoms, or by amino, ester, hydroxyl, and ether groups, or any of the said groups in which the carbon linkage is interrupted by halogen, oxygen or sulfur atoms, or by an amino, ester, hydroxyl; or ether group.

As has been set forth above, X in the general formula represents a dicarboxylic acid residue.

* The linkage between the two carbonyl groups contained in the said dicarboxylic group need not necessarily be interrupted by any of the groups represented by R4 but may be a simple linkage such as is had in oxalic acid. This type of linkage is obtained when oxalic acid is employed as the dibasic acid in the reactions set forth in the present invention. The resultant compounds therefore correspond to the general formula tion, as represented by the above illustrative formulas are prepared by reacting between approximately one mol to two mole of an aliphatic carboxylic acid containing at least six carbon atoms in the aliphatic chain with approximately one mol of a polyamine of the type previously described v at a temperature between approxi mately l5ll-l80 C. until substantially complete reaction is obtained, and thereafter adding approximately one-half mol of a dibasic acid and further reacting the admixture at a temperature between approximately -210 0., de-

pending upon the particular reaction materials employed, until substantially complete reaction is secured as evidenced by the relatively low amine value of the reaction product. The products obtained in this. manner, when cool, are generally tan colored, wax-like materials which are at least. partially dispersible in hot water. In order to insure complete aqueous dispersion of the products of the present invention, it is generally preferable to add a solubilizing agent thereto, such as a lower alcohol, or a peptizing agent, such as an alkali, organic acid, a soap, etc.

Where the amido amine which is to be reacted with a dibaslc acid contains more than one amino group in the molecular chain, more than one dicarboxylic acid residue may be introduced into the structure of the compound by increasing the molecular quantity of the dibasic acid in proportion to the. molecular amount of the amido amine to be reacted. Thusly, where the symbol a and c in. the above illustrative formulae are at least one and where G represents a secondary amino group, a second dicarboxylic acid residue may be incorporated into the structure of the compound, linking at least two of the amino groups represented by G. One example of such a compound and a method whereby the same is obtained are hereinafter set forthin illustrative Example 3.

The compounds of the present invention may be worked up into a concentrated, water soluble softener paste, by treatment of the same with low molecular organic acids such as formic, acetic propionic, and lactic acids. Similarly, water soluble softener pastes which are particularly suitable for application to textile materials may also be prepared by treating the organic compounds obtained according to the processes of the present invention with caustic potash, caustic soda, and similar alkaline materials. Such pastes are usually prepared by heating the compounds to a temperature at which the said compounds are liquid and then adding the said low molecular acid or the alkaline materiahas the case may be, plus an amount of water-sum cient to obtain a paste of the desired'consistency, and stirring the mixture until a smooth, homogeneous composition is obtained. Organio solvents, such as the alcohols previously nentioned, may also be added to the softener 'past'es to obtain improved solubility.

Illustrative of the preparation of the'di-sub s'tituted amido amide derivatives of dibasic acids are the following illustrative examples. The quantities of all materials employed therein are set forth in parts by weight.

. .Emample 1 276 parts of triple pressed'stearic acid and 104 parts of hydroxyethyl ethylene diamine are heated together at 180 Crwhileiremovingthe waterwhichis formed by their interaction; until the acid value of the reaction mixture is reduced to approximately 5 mgm. KOI-I- per gram. This reaction yields approximately 362 parts of a material which consists predominantly of a mixture of materials corresponding to the two formulas:

The above reaction mixture is kept at 180 C. while 67 partsof diglycolic acid are slowly added thereto. As the diglycolic acid is added, a reaction occurs with the evolution of water. After all the diglycolic acid has been added, the temperature of the reaction mixture is raised to approximately 190 C. and kept at that point until further reaction ceases. There is thus obtained approximately 400 parts of material which, at room temperature, is a dark tan, brittle, wax-like material 'having an acid value of approximately 30 mgms. KOH per gram and an amine value of approximately 25 mgms. KOH per gram. The reaction product thus obtained comprises predominantly a'mixture of materials corresponding to the following formulas:

and

n p ep in a fsdftenerflpaste suitable for the treatment of textiles-Q35; parts of the reaction product obtained above are heated with 3 parts of 45% caustic potash and G Zparts of water, and themixture stirreduntiluniform. There is obtained, when cool, a Iight tanc IOred, soft paste which is despersible inhotwater. ,When textiles are padded through atextile treating bath containing 1% of this paste,,.the fabricis. made soft to the touch and has excellent draping qualities. This effect is substantially unaffected by washin; or dry cleaning: When this product is applied to dyed fabricsit has no efiect upon the color shade of thefabriafnor does it produce any deleterious veffection} the, lightlfastness of the u s, n the fabric. t2

The material thus obtained corresponds predominantly to the following formula:

Thereaction' product obtained abovehas amelting" point of approximately 69- C.;" the amine value, as determined by titration,'is 40-50 mgms. KOH per gram.

Depending upon the equipment used and other factors influencing the reaction, it is sometimes necessary to add a 'smalla dditional amount of phth'alic anhydride "to the reaction mixtureito compensate forphthalic anhydride lost by sublimation, thusinsuring-substantial completion of the reaction, --This is likewise truei when using other dicarboxylic acids or derivatives thereof which tend-to distilLsublime o'rdecompose at the reaction' te' 'peratures" used in the present processes.

The reaction product obtained above may be worked up into a water dispersible paste by stiracoaser ring 25 parts of the. said reaction product with 4 parts of acetic acid and 71 parts of water, the temperature while mixing being sufiiciently high to cause the reaction product to melt. When. cool, the resultant paste is light tan colored and forms opalescent solutions when dispersed in hot Water. Cotton fabrics or other textile materials upon immersion in a 1% aqueous solution of this paste, and subsequently dried, have a much softer hand then similar untreated fabrics.

Example 3 276. parts of triple pressed stearic. acid are mixed with 103. parts ofdlethylene triamine and the mixture slowly heated to 130 C. while passing nitrogen therethrough; When the evolution of water ceases, and the acid value of the reaction product. has -dropped to approximately mgms. KOI-I per gram, there are. then slowly added 110 partsfof succinic acid while maintaining the temperature? of the reaction mixture at approximately 185 190!" C. while continuing the passage of nitrogen through the mixture- After all the succinic acid has beenadded, the temwherein R represents the aliphatic residue of coconut fatty acids.

A textile softener paste may be prepared by stirring 20. parts of the reaction product of Ex ample 4 in 80 parts of a 3% tallow soap solution. Textile materials, when treated with an aqueous textile treating bath containing a 0.5% solution of the softener paste, acquire a pleasingly soft feel. This effect is substantially unaffected by washing or dry cleaning.

perature is then further raised to 200-2l0 C., Examme 5 r par 5 o by roxyethy ethylene diamine at 552 12 :3 2232 3: fi igg g g g ggg g zlg: 1'10 C; until the acid value of the reaction product in i the mnowin fcrmulasj 0 falls to less than 5 mgms. KOH per gram. The

g g temperature of the reaction mixture is held at O H H 170 C. while 5.0 grams of anhydrous oxalic acid H 1 are added in small portions. Vigorous agitation 3sf is maintained during the addition of oxalic acid :0 "(3: 5 in order to break the foam which forms. When c addition of oxalic acid has been completed, the k y" temperature of the reaction mixture is raised to E 190 C. and kept at that point until the reaction cro' 0:0 is substantially completed, as indicated by an l 40 amine value less than approximately 30 mgms.

g l I I KOH per gram. The reaction product thus obv tained is a light tan colored wax-like material and having a melting point of approximately C.,

l II it CH', CH;NC'CHa CHQ(JNCH2C 2 0 GnHaa-C- HO OH To prepare a softener paste, 20 parts of the product obtained as described above is heated with 75 parts of water and 5 parts of 4'7 caustic soda, and the mixture stirred until homogeneous. When further diluted with water to a concentration of approximately andapplied to textiles, this product imparts a soft feel to the cloth which is very fast to washing and dry cleaning.

Example 4 225 parts of coconut fatty acids are heated with 148 parts of N,N' dihydroxyethyl ethylene diamine at C. until the acid value of the re-,

- action mixture drops to approximately 5 mgms.

KOH per gramor less. The temperature of the reaction mixture is then raised c0189. (3.,and '74 parts of phthalic anhydride are slowly added thereto. When the addition of the phthalic anhydride to the reaction mixture has beenpom: pleted, the temperature is further raised 110 200? C. and held at that point until thereaotion is completed. Uponcooling a tan colored wax-like and corresponds predominantly to the following formula:

9: with approximately 15 grams of thesoftener paste per liter of water,'and textiles are treated therewith, a very soft, pleasing finish is imparted tothe goods which is not noticeably affected by washing or dry cleaning. Moreover, the finish does not yellow or discolor white goods'nor does it deleteriously affect the lightfastness nor the color shade of dyed fabrics.

Example 6 A concentrated softener paste may be prepared by heating 25 parts of the reaction product obtained above with parts of triethanolamine and 70 parts of water, and stirring the mixture until uniform. When this paste is 'further diluted with water to a concentration of approximately 1% to andapplied to textiles, particularly cellulosic textiles, a marked softening action on the fabric is obtained. I r

Example 290 parts of hydrogenatedufish oil fatty acids are heated to 150 C. and approximately 90 parts of -70%; ethylene diamine are gradually introduced below-the surface of the molten fatty acids. After all the'amine has; been added the mixture is -slo'wly heated to 170 C.-; andkept at that point until the acid value drops to approximately 10 mgrns. 'KOH "per gram. While maintaining tlie-temperati re'of the reaction mixture at 170 C., 120 parts of sebacyl dichloride are slowly added'thereto. There .is a-strong evolution of hydrogen chloride during this addition. After all the sebacyl dichloride has been added the temperature is raised to 200 C. while passing nitrogen through the mixture. Passage of the nitrogen through the mixture assists in removing the hydrogen chloride and helps to cause the reaction to go to completion more rapidly. The reaction product thus obtained corresponds to the following formula:

= f a7- r i-i -oneom-l a. 1 .3.

' 10 in which R1 and R1 represent'the aliphatic residues of hydrogenatedfishoil fattyacids. V When the aminevalue of the above reactio mixture drops to a minimum, the mixture is cooled to approximately C. .15 parts of 45% caustic potash are then'added thereto, followed by 1500 parts of hot water. The mixture is stirred until uniform, and is then allowed to cool. There is obtained approximately 1900. parts of a light tan colored paste. When this paste isfurther diluted'with war'mwater and applied to-textiles, a soft feel is imparted to the textiles; This softening effect is not materially affected by dry cleaning or washing.

Emamplet 225 parts of coconut fatty acids and 116 parts of N,Ndiethyl ethylene diamine are heated together to a temperature of approximately 180 C., and the reaction mixture is maintained at that temperature until the acid value of the mixture drops to less than approximately 10 mgms. KOI-I per gram. To the resulting reaction product there are added, in small portions, 72 parts of phthalic anhydride. Upon completion-of the addition of the phthalicanhydride to the reaction mixture, the temperature ofjthe' reaction mixture is gradually raised to approximately 200 C. and

maintained at that point until reaction is substantially completeyas' evidenced by a low amine value. Upon cooling to room temperature, a light, tan colored wax-like material is obtained.

In preparing a softe'nerpaste for the treatment of textiles employing the'reaction product secured above, the molten reaction product is cooled to a, temperature of approximately C., and

Example 9 288 partsof .caprylic acid are heated to a temperature of approximately C., and 74 parts of propylene diamine are gradually introduced thereto beneath the surface of the acid. The temperature of the mixture is then raised to approximately 180 C. and maintained thereat until reaction is. substantially"complete; as eviden'ced by an. acid "value 'of less than approximately '10 'mgms. 'KO'I-I per grain. Depending upon the equipment 'used and the conditions lof the reaction, when usin'g"a"relatively volatile amin'a'suchflas propylenediainine, it is often found. that a satisfactorily 'low acidvalue bariot belobtained :b i theluse [ofthe theoretical amount of the amine. In sziich case it is'iieessaryto add'an excess of the amine to 7 compensate for the'amin los't'by vapor'at'ion. 'Thereac'tion describedabove yield's approxiniately- 326 parts or a material-which is. ubs'tantially "of the r61- lowing-formulai- The product thus obtained is dissolved in approximately 500 parts toluol and reacted therein with 91.5 parts hexanedioyl chloride at approximately .85 C. in the presence of a hydrogen chloride acceptor such as pyridine. At completion of the reaction, the reaction mixture is quickly transferred into boiling water and the mixture is agitated vigorously. Thereafter the water is drawn off and the toluol removed under vacuum conditions. There is thus obtained approximately 380 parts of a tan, semi-wax-like material, corresponding predominantly to the formula:

The product thus obtained may be dispersed in aqueous solution with caustic, alkali, or acetic acid in such manner as has been set out hereinbefore to form a softener paste which provides improved drape to textile materials when applied thereto and which has no adverse effect on the lightfastness properties of dyestufis.

Example 276 parts of triple pressed stearic acid are reacted with 104 parts of B,B-diaminoethyl ether at 170 C. until the acid value of the reaction mixture drops to less than approximately 5 mgms. KOH per gram. The: temperature of the reaction mixture is then raised to approximately 190 C.; then 59 parts of tartaric acid are added thereto in small portions. The temperature of the reaction mixture is intained at this point until a substantially complete reaction has been obtained as indicated by the relatively low amine value of the reaction Product. The reaction pro uc nsi ts pr domina ly of a compound havin the f rmu A concentrated textile softener paste may be prepared by heating parts of the product of Example 10 with 75 parts of water and about 5 parts of 47% caustic soda, and stirring the mixture until homogeneous.

The hand and texture of textile materials treated with the compounds of the present invention are not only greatly improved over those of untreated fabrics, but the particular properties imparted to the fabric by the use of such compounds may be varied according to thespecific compounds employed. For example, those compounds, in which the aliphatic chain portion represented by R1 and R7 in the illustrated eneral formulas is one containing less than 18 carbon atoms, impart exceptional softening elfects to the fabric, while substantial bodying of the fabric with less softening efiect is had when the compound employed in the treating bath is one in which the "said .aliphatmradicah consist .of chains, contaimngimorethan l8 carbon atom The particularly desirable properties imparted to the textile fabrics bythetrcatment thereof with the p unds ofiihe present invention are subst n ially p manent d e to the substan ivity of these compounds toward textile materials. and particularly towards cellulosic fabrics. Due to the absence of primary amino groups in the compounds of the presentinvention, there is little danger of yellowing or discoloration of the fabric under conditionsilof heat; humidity, .or long storage of the goods. JAshas been pointed out, the finishing agents. of the present invention have no effect upon the colorv shades of dyed fabrics and do not adversely affect thelight' fastne'ss of dyestufis commonly used incoloringftextile :materials. 2 t

While the above products and processes of makingthe same constitute preferred embodimerits of the present invention, changes may be made therein without departing from the scope of the invention as defined in the appended claims.

What is claimed is:

l. A chemical compound corresponding to the formula r( 3-N-[.(C 2)1G]=* CHfir 'N I la 7 s where R1 and R7 are aliphatic chains containing at least 5 carbon atoms; R2 and Rs represent a radical of the group consisting of hydrogen, a lower alkyl radical, and a lower hydroxyalkyl radical; R3 and 35 represent a radical of the group consisting of hydrogen, a lower alkyl radical, a lower hydroxyalkyl radical, and an acyl group containing atleast 6 carbon atoms; G represents a radical of the group consisting of an amino group, a lower alkyl substituted amino group, a lower alkylol substituted amino group, oxygen and sulfur; a and c represent integers from 0 to 6; End e and [represent integers from 1 to 6; X represents a dicarboxylic acid residue in which R4 represents a member of the group consisting of aliphatic, cyclo aliphatic, aromatic, andall;ylaromatic groups; and any of the said groups containing in their structure a member ofthe class consisting of halogen, oxygen, and sulfur atoms, and amino, ester, hydroxyl and ether groups.

2. A chemical compound corresponding to the formula I v 0- R2 a R;

a 't-t-(oHal-nfl where R1 and Prime aliphatic chains containing at least 5 carbon atoms; R2 and Re represent a radical of the group consisting of hydrogen, a lower alkyl radical, and a lower hydroxyalkyl radical; R3 and R5 represent a radical of the represents a dicarboxylic acid residue in which groupconsisting of hydrogen, a lower alkyl radical, a lower hydroxyalkyl radical, and an acyl group containing, at least 6 carbon atoms; band d represent integers from 1 to 6; and where X where R1 and R1 are aliphatic chains containing'at least 5 carbon atoms; R2 and Rs represent a radical of the group consisting of hydrogen, a lower alkyl radical, and a lower hydroxyalkyl radical; R3 and R5 represent a radical of the group consisting of hydrogen, a lower alkyl radical, a lower hydroxyalkyl radical, and an acyl group containing atleast. 6 carbon atoms; G represents a radical of the group consisting of an amino group, a lower alkyl substituted amino group, a lower alkylol substituted amino group, oxygen and sulfur; where a and 0 represent integers from 1 to 6; and where X representsa dicarboxylic acid residue in which R4 represents a member of the group consisting of aliphatic, cyclo aliphatic, aromatic, and alkyl aromatic group; and any of the said groups containing in their structure a member of the class consisting of halogen, oxygen, and sulfur atoms, and amino, ester, hydroxyl and ether groups.

4. Chemical compounds corresponding to the where R. is an aliphatic chain containing at least 5 carbon atoms.

5. Chemical compounds corresponding to the formula where R is an aliphatic chain containing at least 5 carbon atoms.

- Chemical.compounds oi responding' to the formula I R C N C2H4' N C2H4OH r where R is an aliphatic chain containing at -1east 5 carbon atoms.

7. Chemical compounds corresponding to the formula where R is an aliphatic chain containing at least ficarbonatomsj 8. Chemical compounds corresponding .to the formula i r IBCNV-CZH4N =0 ($112 v 'RfiNC2H4-' I where R is an aliphatic chain containing at least 5 carbon atoms.

9. A process for the preparation of a disubstituted amido amide derivative of a disbasic acid which comprises reacting the condensation product of an aliphatic carboxylic acid containing at least 6 carbon atoms and a polyamine, said condensation product containing at least one amino group which contains free hydrogen, at a temperature between approximately C. to 210 C. with a member of the group consisting of aliphatic dicarboxylic acids containing at least 3 carbon atoms, aromatic dicarboxylic acids, alkyl aromatic dicarboxylic acids, cyclic aliphatic dicarboxylic acids, and anhydrides, esters, and acyl halides thereof.

10. A process for the preparation of a disubstituted amido amide derivative of a dibasic acid which comprises reacting an aliphatic carboxylic acid containing at least 6 carbon atoms with a polyamine at a temperature of 150 C. to 180 C.

cyclic aliphatic dicarboxylic acids, and anhydrides, esters and acyl halides thereof.

11. A process for the preparation of a climbstituted amido amide derivative of a dibasic acid which comprises reacting the condensation product of an aliphatic carboxylic acid containing at least 6 carbon atoms and a polyamine, said condensation product having not more than one primary amino group, at a temperature between approximately 150 C. to 210 C. with a member of the group consisting of aliphatic dicarboxylic acids containing at least 3 carbon atoms, aromatic dicarboxylic acids, alkyl aromatic dicarboxylic acids, cyclic aliphatic 'dicarboxylic acids, and anhydrides, esters, and acyl halides thereof, to form a condensation "product *free of primary amino groups.

12. -A process for the preparation of a disubstituted amido amide derivative of a-dibasicacid which comprises reacting an aliphatic carboxylic acid containing at leastfi carbon atoms with a polyamine at a temperature of 150 C. to 180 C. to form a condensation product having not more than one primary amino group, and thereafter reacting said condensation product at a temperature between approximately 150 C. to 210 C. with a member of the group consisting of aliphatic dicarboxylic acids containing at least 3 carbon atoms, aromatic dicarboxylic acids, alkyl aromatic dicarboxylic acids, cyclic aliphatic dicarboxylic acids, and anhydrides, esters, and acyl halides thereof, to form a condensation product free of primary amino groups.

13. A process for the preparation :of .a disubstituted amido amide derivative of'adibasic acid. which comprises reacting the condensation'product of an aliphatic carboxylic acid containing at least 6 carbon atoms and aipolyamine, said condensation product having no primary amino groups and not more than one secondary amino group; -.-at a temperature between approximately C. to 210:C. withxa member of the group consisting of aliphatic dicarboxylic acids containing at least 3:carbo'n atomsaroma'tic dicarboxylic acids; alizyl'aromatic dicarboxylic acids, cyclic aliphatic dicarboxylic acids, and anhydrides, esters and acyl halides thereof, to form a condensation product free of primary and secondary groups. i 3

14. -A process for the preparation .of .a .disubstituited amide amide derivative of a dibasic acid which comprises reacting an aliphatic carboxylic acid containing at least 6 carbon atoms with a polyamine at a temperature of 150 C. to C. to form a condensation product having no primary amino groups and not more than one sec ondary amino group, and thereafter reacting said condensation product at a temperature between approximately 150 C. to 210 C. with a member-of the group consisting of aliphatic dicarboxylic acids containing at least 3 carbon atoms, aromatic dicarboxylic acids, alkyl aromatic dicarboxylic acids, cyclic aliphatic dicar- 'boxylic acids, and an'hydrides, esters, and acyl halides'thereof, to form a condensation product free of primary and secondary amino groups.

' HERMAN B. GOLDSTEIN.

STANLEY I. CLARY.

I REFERENCES CITED TheJfollowing references are .of record in the file "of .this patent:

. UNITEDIST-ATES PATENTS Number 3 Name :Date

3 393 Robinson-ct a1 Aug. 12,1:19 i7

Patent Citations
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US2425393 *Jun 23, 1943Aug 12, 1947Nopco Chem CoHydroxylated polyamide textile lubricants
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2756257 *May 10, 1954Jul 24, 1956Du PontProcess for preparing compositions from 6-caprolactam and hexamethylene diamine
US2832799 *Feb 3, 1955Apr 29, 1958Shell DevAmides of polyunsaturated long chain dibasic acids and resinous products prepared therefrom
US2849400 *Dec 31, 1953Aug 26, 1958California Research CorpGreases thickened with polyamido acid salts
US2849401 *Dec 31, 1953Aug 26, 1958California Research CorpDiamido acid salt grease thickeners
US2863785 *Nov 19, 1953Dec 9, 1958Jelling MurrayThermally stable bituminous bonding materials
US2910374 *Aug 1, 1957Oct 27, 1959Du PontComposition
US2936251 *Dec 5, 1957May 10, 1960Arnold Hoffman & Co IncAmido carboxylic acids
US4077990 *Oct 26, 1976Mar 7, 1978Kewanee IndustriesSurface-active agent
WO1994000418A1 *Jun 29, 1993Jan 6, 1994Ppg Industries IncReaction products of chain-extended polyamine compounds and fatty acid-containing materials
Classifications
U.S. Classification554/57, 252/8.63, 564/153, 554/42
International ClassificationD06M13/405, D06M13/00
Cooperative ClassificationD06M13/405
European ClassificationD06M13/405