US3441953A

US3441953A - Ester of an aliphatic dihydroxy monocarboxylic acid and a textile material treated therewith

Info

Publication number: US3441953A
Authority: US
Inventors: Thomas P Dumont; Herman T Buckley
Original assignee: HERMAN T BUCKLEY
Current assignee: HERMAN T BUCKLEY; Millennium Petrochemicals Inc
Priority date: 1965-10-22
Filing date: 1965-10-22
Publication date: 1969-04-29
Anticipated expiration: 1986-04-29

Description

United States Patent US. Cl. 117-139.5 19 Claims ABSTRACT OF THE DISCLOSURE Ester of an aliphatic dihydroxy monocarboxylic acid. The ester is used in the treatment of a textile material.

This invention relates to esters of aliphatic hydroxy tertiary carboxylic acids and the use thereof as textile assistants and in fiber finishes. More particularly, the invention concerns stable esters formed from dihydroxy tertiary carboxylic acids, and fatty acids, and the use of such esters to modify the properties of textile fibers during processing, or to significantly enhance the qualities of the finished textile material.

Within the past decade considerable progress has been made in the textile finishing art wherein textile assistants are applied to various textile materials derived from both natural and synthetic fibers to render the same more amenable to textile operations or to provide a product which will better serve the user. An ideal textile assistant beneficially modifies the properties of the textile fibers, and is not removed or altered by ordinary washing or dry cleaning procedures. The assistant preferably should be liquid at room temperature and readily dispersible in aqueous media used in textile processing or finishing, or otherwise readily applicable to fibers or textiles. Once applied the assistant should have the property of retention on the fiber without harmful effects such as discoloration, odor, or decreased light fastness of dyed fabrics.

Among the many types of textile assistants may be mentioned softeners used in both regular (nonresin) and resin finishing of textiles to impart a soft full hand and to provide fabrics with enhanced drape. The desired properties in such softeners include stability against heat, oxidation and odor (rancidity) development, resistance to yellowing or scorching, freedom from deleterious effect on the light fastness of dyes, and the right lubricity to maintain or improve fabric sewability. Softeners of anionic, cationic, and nonionic types have been developed which provide a number of these desirable properties, but most are deficient in one respect or another. For example, the anionic sulfonated tallows and oils are subject to odor development through rancidity. These anionics and also nonionics generally have less permanency on the fiber than the cationics. However, the cationics for the most part have a deleterious effect on the light fastness of dyestuffs. Furthermore, many of these types lack stability against either heat or light under textile processing, storage, or use conditions and thus, provide less than optimum results.

It is an object of the invention to provide new carboxylic acid esters of high stability, some of which are advantageously liquid at room temperature, and which may be nonionic, cationic, or anionic in character.

It is an additional object of the invention to provide carboxylic acid esters certain of which possess excellent surface active properties, and are readily water dispersible for general use as emulsifiers, wetting agents, detergents, or dispersing agents.

It is another object of the invention to provide various types of esters of highly stable carboxylic acids having a hindered structure which are variously suitable as textile softeners, lubricants, wetting and rewetting agents, and otherwise as textile assistants in dyeing, washing, scouring, stripping and finishing.

It is a further object of the invention to provide a process for imparting such desirable characteristics as improved softness, scorch resistance, wettability and rewettability, static control, lubricity, tensile and tear strengths, and sewability to textile materials.

It is a specific object of the invention to provide textile softeners characterized by high stability, resistance to yellowing or scorching, good sewability, and which may as an added advantage be liquid for ease of application.

These and other objects, as well as the scope, nature and utilization of the invention will become more clearly apparent from the following description and appended claims.

It has been discovered that certain aliphatic dihydroxy monocarboxylic acids possessing a tertiary carbon atom and represented by the general formula:

1'1. wherein R is a lower alkyl group, and R and R are lower hydroxy alkyl groups, may be esterified with certain compounds to form esters possessing numerous desirable properties. The R group of the dihydroxy monocarboxylic acid preferably contains from about 1 to 4 carbon atoms, as do the R and R lower hydroxy alkyl groups. When R R and R contain 3 or more carbon atoms, the carbon atoms may be joined in either a straight or a branched chain. In all cases, the characteristic hindered structure is present in these dihydroxy monocar boxylic acids, that is, the tertiary carbon atom (without any hydrogen atom bond) in the position alpha to the carboxyl group. This provides the excellent stability of the esters of the invention. The preferred example of a dihydroxy monocarboxylic acid which may be used in accordance with the invention is 2,2-bis(hydrox-ymethyl) propionic acid. It may also be termed Z-methyl, 2-carboxyl-l,3-propane diol, and is represented by the following formula:

OHzOH According to the present invention, the lower hydroxy alkyl groups R and R are preferably esterified with relatively long chain monocarboxylic acids or mixtures thereof, such as the relatively hydrophobic higher fatty acids (C or higher chain length). Such esters may be obtained by heating the reactants in the presence of a conventional esterification catalyst, such as phosphorous acid, sulfuric acid, or p-toluene sulfonic acid. Fatty acids containing from about 7 to 18 atoms per molecule are preferred where hydrophobic chains are desired. However, shorter and longer chain fatty acids may also be employed, the former where the fatty acid need not provide a hydrophobic chain. The fatty acids may suitably be mixtures of saturated or unsaturated monocarboxylic acids which are obtained by the hydrolysis of various natural fats and oils. If desired, unsaturated fatty acids derived from natural fats and oils may be partially or completely hydrogenated prior to reaction with the hydroxy alkyl groups. Illustrative examples of saturated fatty acids which may be employed are pelargonic, capric, lauric, myristic, palmitic, and stearic. Illustrative examples of unsaturated fatty acids which may be employed are myristoleic, palmitoleic, oleic, linoleic, linolenic and elaeostearic.

The carboxyl group of the dihydroxy monocarboxylic acid may be reacted with compounds selected from the following group:

(1) Polyalkylene glycols, or alkylene oxides to produce liquid and solid nonionic polyoxyalkylene triesters suit able as softeners and wetting and rewetting agents,

(2) Simple monohydric alcohols to produce triesters suitable as textile lubricants,

(3) Inorganic or organic bases to form salts of metal bases and amines Which are anionic surface-active agents suitable as softeners, wetting agents, or detergents,

(4) Polyamines or alkanolamines to form aminoesters or amino amides followed by quaternization or neutralization of the amine to form cationic softeners.

Such reactions may generally be conducted either before or after the esterification of the hydroxy alkyl groups R and R The esters of the present invention are either simple triesters, or diester triester-arnine salts, diesteramide amine salts depending upon the specific compound which is selected to react with the carboxyl group of the dihydroxy monocarboxylic acid. Where primary alkanolamines are reacted with the carboxyl group, mixtures of triesters and diester-hydroxyamides are obtained.

When the carboxyl group of the dihydroxy monocarboxylic acid is reacted with a polyoxyalkylene glycol, such as polyoxyethylene glycol or polyoxypropylene glycol, it is preferred that the glycol possess an average molecular 'weight from about 200 to about 2000. Polyoxyalkylene glycols having a molecular weight greater than 2000 and less than 200 may also be employed. The resulting triester is a nonionic surfactant of high stability possessing two hydrophobic groups, and one hydrophilic group joined by a tertiary carbon atom. Instead of employing a polyoxyalkylene glycol to react with the carboxylic group, corresponding quantities of ethylene oxide or propylene oxide or mixtures thereof, may be reacted directly with carboxylic group of the diester to form adducts in situ which result in essentially the same product as if the polyoxyalkylene glycol were initially introduced into the reaction zone. As discussed hereafter, the resulting triesters are advantageously utilized as textile assistants, particularly as textile softeners which result in a fabric possessing excellent scorch resistance, increased tensile and tear strength, and improved sewability characteristics. Such triesters may also be employed in other applications which require a nonionic surface active agents of high thermal stability, for example wetting and rewetting agents in textile processing. These triesters are advantageously liquid depending upon the hydrophobic and hydrophilic group chain lengths. Shorter hydrophobic and hydrophilic chain lengths favor liquid compound formation, while conversely longer hydrophobic and hydrophilic chain lengths favor solid formation.

The carboxyl group of the dihydroxy monocarboxylic acid may be esterified with aliphatic alcohols, saturated and unsaturated, preferably those containing from 1 to 18 carbon atoms. Such alcohols, either long Or short chain, introduce another non-water soluble group into the molecule to produce triesters having utility as lubricants for textiles and fibers. As representative of the various suitable monohydric alcohols may be mentioned saturated alkanols, e.g., butyl, decyl and octadecyl, unsaturated monohydric alcohols, e.g., crotyl, undecenyl and olcyl.

As stated above, the carboxyl group of the dihydroxy monocarboxylic acid may be reacted or neutralized with inorganic or organic bases to form metal salts and amine salts, respectively. Alkali metal or alkaline earth metal hydroxides are preferred as inorganic bases for metal salt formation, but other basic metallic compounds may be employed, such as metallic oxides and metallic carbonates. The term amine salts is intended to include ammonium salts as Well as salts of organic amines. Amines suitable for anionic salt formation include short chain alkyl amines, alkanol amines, and polyamines, such as diamines, and triamines. The resulting diester salts find utility as Wetting agents or anionic textile assistants which impart to textiles highly desirable softness with good nonyellowing and scorch resistance properties.

Amino amides may be formed from polyamines having at least one primary amino group by amide condensation reaction of the diester-carboxylic acid with the primary amine. The remaining free or substituted amino group may then be neutralized with an appropriate acid, pref erably an organic acid such as a lower member of the acetic acid series, or an inorganic acid which will not exert a deleterious effect on the fabric, e.g. boric acid.

If the amine is a polyamine having a primary and tertiary amino group, e.g., diethylaminopropylamine, the resulting amide may be quaternized by alkylation to yield a quaternary nitrogen salt possessing cationic surface active properties. In addition to their suitability as surfaceactive agents for general purposes, these quaternized derivatives are particularly useful as cationic softeners having excellent scorch resistance. Similarly quaternary salts may be formed from tertiary alkanol amines where the carboxylic acid is esterified with the alkanol amine, and the resulting ester-tertiary amine is alkylated, e.g., with methyl bromide, diethyl sulfate, or other suitable alkylating agents.

Textile materials which may be treated with textile assistants in accordance with the present invention include fibers, yarns, and fabrics of natural and synthetic origin. The materials may be cellulosic in nature, such as cotton, rayon or acetate or blends of the same. Synthetic textile materials such as nylon, acrylics, polyesters, polyurethane (spandex), polyolefins and mixtures of the same with natural fibers may also be beneficially treated in accordance with the invention. Softeners of the invention are particularly applicable in regular and resin finishing of cotton and synthetic textiles or blends.

The specific technique chosen to apply the textile assistants to textile materials varies with its function. A preferred technique for softeners involves padding to impregnate the material with a dilute aqueous solution of the assistant. In regular finishing this is followed by drying, while in resin finishing the impregnated or coated material is cured at an elevated temperature to set the resin. Typical concentration for a dilute aqueous solution of the assistant in a softener application range from about 0.5 to 4 percent assistant by Weight. With resin finishing for crease-proofing fabrics, curing temperatures from about -200" C. for a period of about 2 to 15 minutes are recommended for best results. Textiles treated in accordance with the invention, exhibit resistance to discoloration under heat, improved hand, greater tensile and tear strengths and improved sewability characteristics when compared to untreated samples.

Where used as lubricants the assistants may be applied in numerous ways, e.g., by spraying, wicking, or dipping as commonly used and well known in art.

Depending upon the intended use of the esters of the invention, they may be used alone, that is, in full strength without a diluent, such as a solvent or dispersing medium, or they may be prepared in the form of aqueous dispersions or organic solvent solutions. When used in full strength for ease of application to the textile those esters having liquid form are preferred, or if solid, they are applied at temperatures above their melting point.

In general, where the esters are of the type intended to function as textile softeners, it is preferred to prepare them in the form of aqueous dispersions for use in regular finishing, resin finishing, top softening and back filling. Those esters used primarily as textile lubricants are generally applied either from aqueous dispersion or in solvent solution. Of course, where the esters are prepared in the form of hydrophilic salts of amines or a metal cation, such as alkali metals, and are used as wetting or dispersing agents, they are used in conjunction with a DMPA=dimethylolpropionic PEG=polyethylene glycol-followed by a number which indicates approximate molecular weight TEG=triethylene glycol (mol wt. 150) PHTFA=partially hydrogenated tallow fatty acids TEA=triethanolamine DEAPA:diethylaminopropylamine EXAMPLE 1 Preparation of nonionic triesters (a) 107 gm. (0.8 mol) dimethylol propionic acid were reacted with 160 gm. (0.8 mol) polyethylene glycol 200 in the presence of 3.5 gm. (0.5%) phosphorus acid for about two hours at increasing temperature of about 185 to 265 C. over the stated period. The resulting PEG monoester of DMPA in the amount of 220 gm. was then reacted with 376 gm. of partially hydrogenated tallow fatty acids (PHTFA) which is primarily a mixture of palmitic and stearic acids with reduced oleic acid content due to the partial hydrogenation. In approximately an hour and a half reaction time the diesterification reaction was completed at a temperature of 254 under a 28" vacuum during the last half hour of the reaction period. No catalyst was used in the second phase esterification. The product was an oily liquid dispersible in water to form fairly stable dispersions.

(b) Similar nonionic triesters were prepared by the method described above utilizing DMPA and partially hydrogenated tallow fatty acids in the same 2:1 mol ratio. In separate syntheses the DMPA was first reacted with the following polyethylene glycols: TEG, PEG 300, PEG 400, PEG 600 and PEG 1000 in a mol ratio of 1:1.

The TEG and PEG 300 esters were oily liquids at room temperature like the PEG 200 ester, while the higher molecular weight polyethylene glycol esters were all solid at room temperature increasing in hardness with increase in molecular weight from soft paste to a semihard wax which melts in the hand.

In the preparation of the DMPA-PEG 1000 type triester, stearic acid was employed to form the fatty acid diester rather than the partially hydrogenated tallow fatty acids. This higher molecular weight triester formed a water dispersible gel at relatively high concentrations up to 25% in hot water.

TEXTILE SOFTENERREGULAR FINISH Samples of each of the foregoing nonionic triesters were prepared in aqueous dispersion at a 0.5% active level and were padded onto 80 x 80 cotton cloth and the samples were then dried for testin gas as a softener in regular (nonresin) textile finishing. The TEG and PEG 200 esters were dispersed with addition of 5% Igepal CO630, a commercial ethoxylated alkylated phenol dispersing agent. The other triesters were self-dispersible. The triesters preapred from PEG 600 and PEG 1000 did not provide quite as good a hand when judged by a panel of observers compared with a commercial textile softener, Emersoft 7700, a nonionic softener of the fatty acid amide type. The panel rated the hand of the TEG and PEG 200 triesters as superior to and the PEG 300 and 400 triesters as comparable to the commercial softener.

The scorch resistance of the softener-treated textile is determined by subjecting samples of the textile to heating for a period of one minute at a temperature of 400 F. between platens of an Atlas scorch tester. The sample is then measured for discoloration in a standard reflectometer by reading the percentage of incident light reflected by the sample at threedifierent wave length ranges or colors, amber (a), blue (b) and green (g). A quantitative yellowness factor is calculated from the formula w i x1000 Those samples of the textiles treated with the nonionic triester softeners which provides comparable or superior hand were subjected to the above-described scorch test. The yellowness factors of the tested triesters were substantially equivalent to one another and superior to the scorch resistance of the above-mentioned Emersoft commercial softener.

EXAMPLE 2 Preparation of additional nonionic triesters 234 gm. of DMPA were reacted with 525 gm. of PEG 300 providing a 1:1 mol ratio in the presence of 3.8 gm. (0.5%) phosphorous acid. The reaction was conducted over a period of two hours at temperatures of 200-260 C., and the reaction mixture was held under 28" vacuum for the last half hour of the reaction period until the free acid content was reduced to 1.85%. A mixture of monomeric fatty acids consisting primarily of C to C straight chain aliphatic monocarboxylic acids with a small quantity of branched acids derived from dimerization of tallow fatty acids were reacted with the previously prepared PEG 300 monoester of the DMPA in a ratio of 2 mols of acid mixture to 1 of monoester. The reaction mixture was raised to a temperature of 250 C. cover a two hour period and held under 28" vacuum for an additional hour at 250 C. until the free acid content was reduced to 2.9%. The resulting triester was a yellow colored liquid at room temperature which formed a paste at about 18 C. and was readily emulsifiable when poured into water.

TEXTILE SOFTENER-RESIN FINISH The triester of this Example II, commercial Emersoft 7700 softener, DMPA-PEG ZOO-PHTFA esters and the DMPA-PEG 300-PHTFA esters were padded at room temperature onto samples of x 100 cotton fabric at a 0.7% active level in admixture with 16% Rhonite R-l, a dimethylolethylene urea wash and wear resin, 0.1% Triton X-100 an ethoxylated nonyl phenol, and 0.5% magnesium chloride. The samples were partially air dried and then ironed dry. Due to the resin content, the samples were then cured at C. for five minutes subject to a mild wash and two rinses at 40 C., air dried and then again ironed. Untreated cotton fabric samples were also included in the tests reported below as a control or blank.

The soft hand of all of the nonionic DMPA triesters was equal to or superior to that of the commercial Emersoft 7700 and vastly superior to the untreated fabric.

The scorch resistance (yellowness factor) of all of the nonionic DMPA triester treated samples were equal or superior to the untreated blank and much superior to the commercial softener treated sample.

In sewability (measured by the average percentage of warp and fill yarns broken when the textile sample is Preparation of fatty acid diester-carboxylate salts 134 gm. of DMPA was reacted with 320 gm. of

pelargonic acid providing a ratio of one mol DMPA to two of pelargonic in the presence of 3.6 gm. (0.5%) phosphorous acid catalyst. The reaction mixture was heated up to about 240 C. over a two hour period and held at 240 C. under a vacuum of 28 for approximately one hour to complete the reaction as indicated by reduction of the free pelargonic acid content to 0.6%. The resulting DMPA dipelargonate ester containing the free carboxyl group was neutralized in aqueous solution with alkali by reacting 50 gm. of the ester-acid with 9 gm. of a 50% sodium hydroxide solution to provide a diester salt having a pH of 7.4 in a 1% aqueous solution. The diester salt was tested as a wetting agent at a concentration of 2 gm. per liter by the well-known Draves wetting test at 29 C. and provided a wetting time of 10.0 seconds compared to 19.5 seconds for a sulfated propyl oleate wetting agent and compared to 10 seconds for a well-known wetting agent, Triton X100 (an alkylated ethoxylated phenol).

EXAMPLE 4 Preparation of cationic triester and diester amide salts (a) 308 gm. of DMPA were reacted with 1240 gm. of partially hydrogenated tallow fatty acids providing a 2:1 mol ratio of fatty acid to DMPA using 3.9 gm. (0.25%) phosphorous acid catalyst. The reaction was conducted for approximately two hours with the temperature gradually increasing from 170 to 247 C. 256 gm. of the resulting diester-acid was reacted with 61.5 gm. of triethanol amine without a catalyst providing a mol ratio of approximately 1:1 based on a molecular weight of 638 for the DMPA-fatty acid diester. This esterification reaction was conducted at temperatures of 216 to 226 C. for approximately one half hour and then held at 28" vacuum until the acid value was reduced to 6.4. The resulting triester amine had an amine value of 51.5 indicating a 71% conversion calculated on the basis of a molecular weight of 774 for the product, 54.5 gm. of the triester amine were neutralized with 3 gm. of glacial acetic acid to form a water dispersible cationic amine salt.

(b) 255 gm. of the diester of DMPA and partially hydrogenated tallow fatty acids prepared as in part (a) of this example were condensed with 78 gm. of diethylaminopropylamine in the absence of catalyst to form the diester-amino amide. This charge of reactants provided 1.2 mols of amine for each mol of diester-acid and the reaction was conducted at a temperature range of 180- 250 C. for a period of about three hours until the acid value was reduced to 1.9% utilizing vacuum in the last twenty minutes. The amine value of the resulting amide condensate was 95.5 indicating a yield in excess of theoretical based on a molecular weight of 784 for the diester amino-amide product. 59 gm. of the diester amino amide was neutralized with glacial acetic acid in equal mol proportion to form a water dispersible amine salt.

The cationic amine acetate salts prepared according to parts (a) and (b) of this example were tested as cationic softeners in comparison with two commercial cationic softeners known as Cargill Q2 HT-75 and Emery 3518-T. Each of the softeners was padded at room temperatures at 0.5% concentration level onto 80 x 80 cotton fabric. The hand of the fabric softeners treated with the amine salts of this example was comparable with that of the commercial cationic softeners and the scorch resistance of the triethanol amine salt of part (b) of this example was superior to both the commercial cationic softeners, while the diethylaminopropylamine salt at least comparable in scorch resistance to these commercial softeners.

EXAMPLE 5 Preparation of nonionic triester The DMPA dipelargouate-mono PEG 1000 triester was prepared according to the method of Example 1 and then utilized as a wool degreasing agent. gm. samples of the wool stock were carded and blended until uniform. Half of the sample was extracted with ether to determine total grease content. The other half of the sample was given one 10 minute wash followed by one 5 minute wash at 50 C., and then was rinsed once for 10 minutes and once for 5 minutes at 50 C. The nonionic triester degreasing agent was added to the wash water at a concentration of 0.3%. Approximately of the wool grease was removed by the nonionic triester as determined by weight differences between the treated sample and the ether extracted sample. The foregoing indicates degreasing agent utility of the high molecular weight triester prepared from PEG 1000.

EXAMPLE 6 Preparation of anionic diester salts The ammonium salt of the DMPA diester of partially hydrogenated tallow fatty acid was prepared by neutralizing 638 parts of the diester with parts of a 28% ammonia solution in 1937 parts of water. The resulting salt formed a relatively heavy gel when the aqueous mixture was heated to 60 C. but was rendered more fluid by addition of small amounts of sodium sulfate solution. Padded on textiles at a 1% level, this anionic salt provided an excellent hand more like the raggy hand characteristic of cationic softeners.

The partially neutralized or half ammonium salt of the corresponding diestearyl ester of DMPA was prepared by reaction of 31.9 gm. of the diestearyl DMPA ester with 3.1 gm. of 28% ammonia in 131 gm. of water. The resulting heavy gel-paste dispersed readily in warm distilled water and when compared with commercial anionic softeners padded onto 80 x 80 cotton fabric at 1% concentration it provided a much softer hand with a comparable scorch resistance.

EXAMPLE 7 Preparation of hydrophobic triester 191 gm. of the DMPA diester of distilled tallow fatty acids prepared by the method of Example 1 were reacted with 26 gm. of crotyl alcohol (CH CH CHOH OH) providing a 20% excess of alcohol over diester-acid in the presence of 1.1 gm. of 50% phosphorous acid. The reaction mixture was heated over a two and a half hour period with the temperature increasing from 137 to 205 C. The free acid content calculated on the DMPA diester acid indicated approximately 50% yield of the DMPA-fatty acid diester-monocrotyl ester. The product is useful as a textile lubricant or fiber finish.

All percentages given herein are by weight except where otherwise indicated.

Although many preparations of compounds according to the invention are exemplified above, various other fatty acids have been and may be employed to esterify the hydroxyl groups of the dihydroxy monocarboxylic acids. -In addition, the carboxyl group of the 2,2-hydroxyalkyl alkanoic acids of the invention may be reacted with many other inorganic bases, amines, and mono and polyhydric alcohols to provide compounds equivalent to those exemplified above.

The esters of the invention may be represented by the following general formula RZOOGR4 R3OOCR5 where R is a lower alkyl, R and R are lower alkylene groups, R; and R are the same or different branched or straight chain hydrocarbyl groups, R R and R preferably having 1 to 4 carbon atoms, and R and R preferably having from 6 to 17 carbon atoms, and wherein X is a member of the group consisting of:

(Oxyalkylene) H where n is an integer providing a molecular weight of between and 2000,

OM wherein M is an alkali metal or alkaline earth metal,

ONHRsRqRg, and

O(lower alkylene)N-R R- or NH(lower alkylene)NR R in acid salt form wherein R R and R are hydrogen, lower alkyl and hydroxy alkyl. The lower alkyl groups preferably have 1 to 4 carbon atoms and the lower alkylene groups preferably have 2 to 4 carbon atoms.

It is to be understood that further variations and modifications may be resorted to as will be apparent to those skilled in the art. Such variations and modifications are to be considered within the purview and scope of the claims appended hereto.

Having described our invention, what we claim is:

1. An ester of a dihydroxy monocarboxylic acid represented by the following general formula:

it. wherein R is a lower alkyl group, and R and R are lower hydroxy alkyl groups, in which ester both of the hydroxyl groups of said acid are esterified with a fatty acid, and the carboxyl group of said dihydroxy monocarboxylic acid is reacted to provide a structure selected from the group consisting of a polyoxyal kylated ester, a monohydric alcohol ester, a metal salt, an amine salt, and an acid salt of an aminoester or an amino amide.

2. An ester according to claim 1 in which R is an alkyl group of from about 1 to 4 carbon atoms.

3. An ester according to claim 1 in which R and R are lower hydroxy alkyl groups of from about 1 to 4 carbon atoms.

4. An ester according to claim 2 in which the hydroxyl groups R and R are esterified with a higher fatty acid having at least 7 carbon atoms.

5. An ester according to claim 1 in which the compound which is reacted with the carboxylic group is polyoxyalkylene glycol having an average molecular weight from about 200 to 2000.

6. An ester according to claim 1 in which the compound which is reacted with the carboxylic group is a monohydric aliphatic having from about 1 to 18 carbon atoms per molecule.

7. An ester according to claim 1 in which the compound which is reacted with the carboxylic group is an alkali metal or alkaline earth hydroxide.

8. An ester according to claim 1 in which the carboxylic group is neutralized with ammonia or an organic amine.

9. An ester according to claim 1 in which the carboxylic group is reacted with an amine having at least two amine groups one of which is a primary amine group to form an amino amide and the resulting amino amide is neutralized with an acid to form a cationic amine salt.

10. An ester according to claim 1 in which the carboxylic group is reacted with a trialkanolamine to form an amino ester and the resulting amino ester is neutralized with an acid to form a cationic amine salt.

11. A triester of 2,2-bis(hydroxymethyl)propionic acid wherein the hydroxyl groups are esterified with a higher fatty acid of 7 to 18 carbon atoms and the carboxyl group is esterified with a polyoxyalkylene glycol having a molecular weight of from 200 to 2000 and selected from the group consisting of polyoxyethylene glycol and polyoxypropylene glycol.

12. A diester of 2,2-bis(hydroxymethyl)propionic acid wherein the hydroxyl groups are esterified with a higher fatty acid having 7 to 18 carbon atoms and the carboxyl group is neutralized with an inorganic base or an organic amine.

13. A diester of 2,2-bis(hydroxymethyl)propionic acid wherein the hydroxyl groups are esterified with a higher fatty acid having 7 to 18 carbon atoms and the carboxyl group is neutralized with ammonia to form the anionic salt of said ester.

14. A diester of 2,2-bis(hydroxymethyl)propionic acid wherein the hydroxyl groups are esterified with a higher fatty acid having 7 to 18 carbon atoms and the carboxyl group is reacted with an alkylene polyamine or an alkanol amine to form the corresponding amino amide or amino ester, respectively, of said acid and said amino amide or amino ester is neutralized with an acid to form the cationic salt.

15. A textile material treated with a softening amount of an ester of claim 1.

16. A textile material treated with a softening amount of a triester of claim 11.

17. A textile material treated with a softening amount of a triester of claim 11 as a nonionic softener in which the polyoxyalkylene glycol is polyoxyethylene glycol having an average molecular weight of 200, and the higher fatty acid is predominantly saturated with a C to C chain length.

18. A textile material treated with a softening amount of the diester ammonium salt of claim 13.

19. A textile material treated with a softening amount of the cationic acid salt of an aminoamide or aminoester of claim 14.

References Cited UNITED STATES PATENTS 2/1936 Holt 260-488 4/1967 Ruhf 260-535 WILLIAM D. MARTIN, Primary Examiner. THEODORE G. DAVIS, Assistant Examiner.

U.S. DEPARTMENT OF COMMERCE PATENT OFFICE Washington, D.C. 20231 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No 3 ,441 ,953 April 29 1969 Thomas P. Dumont et a1.

It is certified that error appears in the above identified patent and that said Letters Patent are hereby corrected as shown below:

In the heading to the printed specification, lines 5 to 7, "(2666 Losantiville Ave. Cincinnati, Ohio 45237) and Herman T. Buckley, 6233 Sharlene Drive, Cincinnati, Ohio 45211" shoulr read and Herman T. Buckley, Cincinnati, Ohio, assignors tr Emery Industries, Inc. Cincinnati, Ohio, a corporation of Ohio Signed and sealed this 14th day of April 1970.

(SEAL) Attest:

WILLIAM E. SCHUYLER, JR.

Commissioner of Patents Edward M. Fletcher, Jr.

Attesting Officer