US3649535A

US3649535A - Preparation of finish composition for synthetic fibers

Info

Publication number: US3649535A
Application number: US28249A
Authority: US
Inventors: John E Clark; Michael R Cusano
Original assignee: Standard Chemical Products Inc
Current assignee: Henkel Corp; Standard Chemical Products Inc
Priority date: 1970-04-17
Filing date: 1970-04-17
Publication date: 1972-03-14
Anticipated expiration: 1989-03-14

Abstract

FINISH COMPOSITIONS FOR IMPARTING ANTI-STATIC AND LUBRICATING PROPERTIES TO SYNTHETIC FIBERS COMPRISING (A) AN AMINE SALT OF A CARBOXYLIC ACID ESTER OF AN A-SULFONATED FATTY ACID AND (B) A HIGH MOLECULAR WEIGHT FATTY ACID ESTER AND METHOD OF TREATING SYNTHETIC FIBERS.

Description

United States Patent O Int. Cl. D06m 1/18, 3/20 U.S. Cl. 2528.75 23 Claims ABSTRACT OF THE DISCLOSURE Finish compositions for imparting anti-static and lubricating properties to synthetic fibers comprising (A) an amine salt of a carboxylic acid ester of an m-sulfonated fatty acid and (B) a high molecular weight fatty acid ester and method of treating synthetic fibers.

PRIOR APPLICATIONS This application is a streamlined continuation of copending commonly assigned application Ser. No. 579,844 filed Sept 16, 1966, now abandoned, which in turn is a continuation-in-part application of co-pending, commonly assigned application Ser. No. 346,390, filed Feb. 21, 1964, now abandoned, and application Ser. No. 494,969, filed Oct. 11, 1965, now abandoned, which in turn is a continuation-in-part application of application Ser. No. 269,186, filed Mar. 27, 1963, now all abandoned.

The invention relates to novel finish compositions for synthetic fibers and to a novel method of treating synthetic fibers to impart lubricating and anti-static properties thereto. The invention particularly relates to finish compositions comprised of an amine salt of a carboxylic acid ester of an a-sulfonated fatty acid and a high molecular weight fatty acid ester.

The advent of thermoplastic static forming fibers, (polyester, nylon, acrylic, polyethylene, polypropylene, etc), all of which involve high-temperature processing for drawing or heat stretching created new technical problems concerning finishes both from the standpoint of the processing by the yarn producer as well as the yarn processor and fabric manufacturer. At the present time finishes for these fibers are being applied both from aqueous media and from petroleum solvents.

Such finishes are generally applied to the fibers to give a lubricating and antistatic effect during subsequent processing, such as heat drawing or stretching. Thus the spin finishes are applied after spinning and before heat stretching and drawing. For example, the molten polymer may be extruded through a spinneret, either as a monofilament or a multifilament fiber, and the finish composition would be applied almost immediately after the formation of the fiber. Heat stretching and drawing would follow to impart strength, etc., to the fiber. Some typical processes are disclosed, for example, in US. Pats. Nos. 2,803,408, 2,803,109 and 3,025,650 to Stoddard et a1. Such finishes may often be removed prior to dyeing,

The finishes must fulfill certain requirements. They should provide the needed lubricating and antistatic effect. In addition they should be easy to apply and remove when desired, have good thermal and chemical stability, and should not adversely affect the fiber.

OBJECTS OF THE INVENTION It is an object of the invention to provide a novel finish Ice composition for synthetic fibers during the processing thereof.

It is a further object of the invention to provide a novel lubricating and antistatic composition for synthetic fibers.

It is another object of the invention to provide a composition for synthetic fibers which is stable under fiber processing conditions, does not adversely affect the fiber or subsequent processes applied to the fiber, and which may be easily applied and removed.

It is an additional object of the invention to provide a novel process for imparting antistatic and lubricating properties to synthetic fibers.

These and other objects and advantages of the invention will become obvious from the following detailed description.

THE INVENTION The novel finish compositions of the invention consist essentially of (1) an amine salt of a carboxylic acid ester of an a-sulfonated fatty acid having 8 to 22 carbon atoms in the acid moiety, the alcohol portion of the said ester being selected from the group consisting of alkanols of l to 22 carbon atoms, polyethylene glycols having 2 to 205 ethylene oxy groups, alkylene polyols of 2 to 8 carbon atoms and fatty alcohols of 8 to 22 carbon atoms ethoxylated with 1 to 205 moles of ethylene oxide and the amine being selected from the group consisting of alkanolamines, alkyl amines and polyalkylene polyamines of 8 to 22 carbon atoms and (2) a high molecular weight fatty acid ester having 8 to 22 carbon atoms in the acid moiety and 1 to 22 carbon atoms in the alcohol moiety, and a minimum total carbon atom content of 22 in a ratio of 1:99 to 99:1. A preferred ratio is :25 to 25:75.

The said compositions may also contain up to 5% by weight of the composition of a bactericide.

The carboxylic acid ester of the a-sulfonated fatty acid can be prepared by reacting one or more mixtures of an a-sulfonated fatty aicd of 8 to 22 carbon atoms with an alcohol, glycol, or ethoxylated alcohol such as hexadecyl alcohol, polyethylene glycol 600 or Alfonic 10126, to form the corresponding ester of the carboxylic acid group. In the case of a glycol, if one mole of the alpha-sulfonated fatty acid is reacted with one mole of the glycol, monoester of the polyhydric compound is formed as illustrated by Equation I:

If two moles of the a-sulfonated fatty acid is reacted with one mole of the glycol, a diester of the polyhydric compound is formed as illustrated by Equation II.

Esterification with an ethoxylated alcohol is shownby Equation. -III.

s 03H ROHCOOH a'onaoomormnon --r s 03H n-onooowmommuoiim' H20 In Equations 1, J1 and III, R represents an aliphatic radical having 6 to 20 carbon atoms and n is an integer from 1 to about 205.

After esterification, the sulfonic acid group is neutralized with the desired amine such as diethanolamine to a pH on the alkaline side. Since the reaction is carried out in the presence of a solvent such as VM&P Naphtha, said solvent is almost completely distilled off. Then the above finished ester is compounded with the high molecular weight ester, for example, hexadecyl stearate or butyl stearate, in an approximate 50/50 ratio. However, this ratio is not to be implied as a limitation and may vary from 1:99 to 99:1. A small percent from to of a suitable bactericide, for example, Dowicide 1, may be incorporated into the composition, as desired.

An advantage of using glycols or ethoxylated alcohols as esteritication agents is that by selective choice of the hydrophile, the molecule in addition to being solvent miscible, can also be made water soluble or dispersible.

In addition to compounding said ester with a fatty acid ester of a monoalcohol, e.g., hexadecyl stearate, butyl stearate; fatty acid monoand diesters of glycols may be used, for example: polyethylene glycol 600 monolaurate; or fatty acid esters of ethoxylated alcohols may be used, for example, ethoxylated tridecyl alcohol 6 moles ethylene oxide) stearate, provided that the combined carbon content of the fatty acid moiety and glycol or ethoxylated alcohol moiety totals at least 22 carbon atoms.

The above composition can also be prepared in a onestep operation by esterifying both the alpha sulfo-fatty, and stearic acids together with an alcohol, glycol or ethoxylated alcohol such as hexadecyl alcohol, polyethylene glycol 600 or Alfonic 1012-6, or mixtures thereof. After removal of the solvent by distillation, the required amount of preservative is added.

A large variety of alcohols and mixtures thereof may be used in accordance with the process of the disclosure to form the ester of the alpha-sulfo fatty acid. The alcohols may contain from about 1 to 22 carbon atoms and preferably are alkanols. Among these may be mentioned the lower alcohols, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, Z-methyl-l-butanol, amyl, l-hexyl, .2-methyl-l-pentyl, 2-ethylbutyl, Z-ethyl-hexyl alcohols. But more preferably from the standpoint of volatility the higher molecular weight alcohols are employed, for example, decyl, dodecyl, tridecyl, hexadecyl, and eicosyl alcohols.

A large variety of glycols and mixtures thereof may be used in accordance with the process of the disclosure. Among these may be mentioned the lower glycols, for example: ethylene glycol, diethylene glycol, triethylene glycol, tetra-ethylene glycol, propylene glycol, dipropylene glycol, 1,5-pentanediol, hexylene glycol, 2-methyl-2- ethyl-1,3-propanediol, 2-ethyl-l, 3-hexanediol, 1,2,6-hexanetriol, neopentyl glycol; but more preferably from the standpoint of volatility, the higher molecular weight glycols for example: polyethylene glycol 200, polyethylene glycol 300, polyethylene glycol 400, polyethylene glycol 600, polyethylene glycol 1000, polyethylene glycol 1500, polyethylene glycol 1540, polyethylene glycol 4000, polyethylene glycol 6000, polyethylene glycol 9000 and the like.

Various ethoxylated alcohols and mixtures thereof may be used in accordance with the process of the disclosure to form the ester of the alpha-sulfofatty acid. Such alcohols include, for example, the alcohols ranging from C -C which have been ethoxylated with 1 to 20 moles of ethylene oxide; examples of which are Alfonic 1218-6, Alfonic 1012-6, Alfonic 1218-7, Alfonic 1218-8; polyoxyethylene (6) ether of tridecyl alcohol, (Glycosperse TBA-6), POE 4 lauryl alcohol and the like.

.A large variety of amines and mixtures thereof may be used in accordance with the process of this disclosure for neutralizing the sulfo-group. Among these are the alkanolamines, for example: monoethanolamine, dieth anolamine, triethanolamine, N-methyl ethanolamine, N-ethyl diethanolamine, monoisopropanolamine, diisopropanolamine, triisopropanolamine, mixed isopropanolamine; or alkyl amines, for example, ethyl amine, diethyl amine, triethyl amine, propyl amine, dipropyl amine, dipropyl amine, isopropyl amine, diisopropyl amine, butyl amine and the like having up to 22 carbon atoms, or alkylene polyamines such as ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, propylene diamine and the like.

Various esters and mixtures thereof may be used in accordance with the process ofthe present disclosure as the additional component of the finish composition. These esters may have from about '8 to 22 carbon atoms in the acid moiety and from 1 to 22 carbon atoms in the alcohol moiety, with a minimumtotal carbon atom content of 22 in the combined acid and alcohol, or glycol, or ethoxylated alcohol moieties. Among these may be mentionedbecause of volatility preferably .the higher molecular weight esters, for example: butyl stearate, octyl stearate, decyl stearate, dodecyl stearate, tridecyl stearate, hexadecyl stearate, eicosyl stearate, and the like. High molecular weight esters of other fatty acids may also be used, such as butyl arachidate, butyl behenate, octyl myristate, octyl palmitate, octyl arachidate, octyl behenate, decyl laurate, decyl myristate, decyl palmitate, decyl arichidate, decyl behenate, dodecyl caprate, dodecyl laurate, dodecyl myristate, dodecyl palmitate, dodecyl arichidate, dodecyl behenate, tridecyl caprate, tridecyl laurate, tridecyl myristate, tridecyl palmitate, tridecyl arichidate, tridecyl behenate, hex-' adecyl caprylate, hexadecyl caprate, hexadecyl laurate, hexadecyl myristate, hexadecyl palmitate, hexadecyl arichidate, hexadecyl behenate, eicosyl myristate, eicosyl palmitate, eicosyl arichidate, eicosyl behenate and the like, as well as corresponding unsaturated esters, although saturated compounds are preferred.

In addition, high molecular weight esters of glycols or ethoxylated alcohols may be used, for example, polyethylene glycol 400 dilaurate, polyethylene glycol 600 monostearate, polyethylene glycol 1000 monostearate, polyethylene glycol 400 di-tririci-noleate, polyethylene glycol 600 monolaurate, or Alfonic 1218-6 laurate, Alfonic 1012-6 stearate, Alfonic 1218-8 oleate and the like.

It is critical that the combined carbon content of th high molecular weight fatty acid ester be a minimum of 22. As was pointed out above, antistatic and lubricating finishes are generally applied after the yarn or filament is formed and prior to the drawing or heat stretching treatment. In this latter operation, temperatures of 200 C. are reached, and in some instances, even higher. Under these temperature conditions, if the combined carbon content were less than 22, the finish composition would not be suitable for the heat treating operation and the finish composition would either (1) smoke excessively, (2) volatize or (3) decompose. Since the object of the producers finish is to provide lubricity and anti-static properties for subsequent processing, any loss of finish due to the above three reasons results in ditficulties in processing. For example, smoking of a finish, in addition to loss of finish, is objectionable from a health hazard standpoint and would result in extreme discomfort to personnel. Volatility will severely effect the lubricity and anti-static properties of the yarn. Loss of anti-static protection would cause ballooning of multifilament yarns due to friction as the yarn runs over the guides. This ballooning, loss of antistatic protection would make it impossible to process the yarn and could shut down a plant. Lack of lubricity could result in broken filaments, snarling, etc. Decomposition could result in polymerization of the finish, a varnish type residue would be formed, a tackiness or gumminess is imparted to the yarn and once again the yarn would be difiicult to process. Of course, higher levels of producers finish could be applied to offset any loss due tothe elevated temperatures, but this would only accentuate the above problems of smoking, volatility, decomposition, etc.

A large variety of preservatives or mixtures thereof, as known in the art, may be used in accordance with the process of the present disclosure. Among these may be mentioned Dowicide 1 (ortho phenylphenol), Dowicide A (sodium o phenylphenate), tris(hypdroxymethyl)nitromethane, and Dowicide 4 (2-chloro-4-phenylphenol). The preservative is used only as a bactericide and is not essential to the composition to provide the beneficial properties thereof. Thus the preservative may be omitted.

These compositions can be applied as spin finishes for synthetic fibers such as polyester, nylon, acrylic, polyethylene, polypropylene and the like. These fibers can subsequently be processed into weaving yarns, knitting yarns, tricot or Raschel yarns, tire yarns, and industrial yarns. The finishes can also be applied to non-synthetic fibers which have been coated with a synthetic layer on their surface.

These new compositions meet the requirements for a finish composition since they possess the following advantages:

(1) Excellent lubricity.

(2) Excellent anti-static properties.

(3) Good thermal and chemical stability.

(4) Low volatility.

(5) Good drawing properties.

(6) Easily removed.

(7) Does not affect physical and chemical properties of the yarn.

(8) Good spreading properties.

(9) No adverse effect on dyeing properties.

It has been found that the inventive finish composition has an especially advantageous use in coating synthetic tire cords, e.g., nylon, polyester cords. A spin finish can either add to or detract from the adhesion properties of the yarn to the rubber in a tire. Thus, in the case of nylon cord, the cord with a spin finish on it first goes into a dip preparation bath which, for example, contains a vinyl pyridine latex and a resorcinol-formaldehyde resin. The dip preparation provides the adhesion between the cord and the rubber in the tire. The spin finish, if not compatible with the dip preparation, can hinder the adhesion properties. By using the composition of this invention, as spin finishes, it has been unexpectedly discovered that the adhesion properties of the whole system are markedly improved. This phenomenon has also been obsenved with other synthetic fibers, such as polyester cord, although a different dip preparation is utilized and the dip is applied in a multi-stage operation in the case of polyester tire The novel method of the invention of imparting lubricating and anti-static properties to synthetic fibers comprises applying to synthetic fibers 0.1 to 5.0%, preferably 0.9 to 1.0% by weight of a composition comprised of (1) an amine salt of a carboxylic acid ester of an a-sulfonated fatty acid having 8 to 22 carbon atoms in the acid moiety, the alcohol portion of the said ester being selected from the group consisting of alkanols of 1 to 22 carbon atoms, polyethylene glycols having 2 to 205 ethylene oxy groups, alkylene polyols of 2 to 8 carbon atoms and fatty alcohols of 8 to 22 carbon atoms ethoxylated with 1 to 205 moles of ethylene oxide and the amine being selected from the group consisting of alkanolamines, alkyl amines and polyalkylene polyamines of 8 to 22 carbon atoms and (2) a high molecular weight fatty acid ester having 8 to 22 carbon atoms in the acid moiety and 1 to 22 carbon atoms in the alcohol moiety, or 2 to 410 carbon atoms in the glycol moiety or 10-432 carbon atoms in the ethoxylated alcohol moiety, and a total carbon atom content of not less than 22 in a ratio of 1:99 to 99:1.

The finish compositions may be applied to the fibers in any suitable manner such as by roll, wick, spray, dip, neat, etc. The finish compositions are usually diluted with water or a petroleum solvent such as Varsol, to a concentration of l to 25%, usually about 20%, by weight. However, the

compositions may also be applied neat, sometimes referred to as straigh or whole oil.

In a roll application, the roll, whish may be made of stainless steel, polished chrome steel or ceramic, is partly immersed in the finish emulsion contained in a trough. As the roll turns, the finish emulsion is picked up by the roll and the yarn or fiber, which travels in the same or opposite direction of the roll, comes in contact with the roll and picks up the desired level of finish emulsion. The amount of finish emulsion picked up by the fiber depends upon many factors such as speed of the fiber, r.p.m. of the roll, concentration and viscosity of the finish emulsion, angle of contact of the fiber with the roll, temperature of the bath, direction of rotation of the roll, etc.

In the following examples, there are illustrated several preferred embodiments. However, it should be understood that the invention is not intended to be limited to the specific embodiments.

EXAMPLE I Armosul 16 (alpha-sulfopalmitic acid690 g. (2.00

moles) Hexadecyl Alcohol-492 g. (2.00 moles) VM&P Naphtha-1180 g.

Diethanolamine-24O g. (2.28 moles) The first three reactants are charged into a 3-neck flask equipped with agitator, thermometer and Dean-Stark distillation trap attached to a reflux condenser, and warmed under agitation to a temperature of 106 C. (reflux temperature). -At this point water of distillation begins to collect in the trap. The reaction is allowed to mix for 2 hours to a top temperature of C. At the end of this time, 72 grams of water is collected in the trap.

Free Organic Acidity (as Oleic Acid) =3.6%.

The reaction is cooled to 35 C. and the required amount of diethanolamine is added. The reflux condenser and trap are replaced with a downward condenser for the purpose of recovering the solvent. The mixture is heated to a temperature of 220 C. at atmospheric pressure in order to remove most of the solvent. 'If it is desired to completely remove the solvent, this can be done by heating to 220 C. under 1 mm. pressure (in vacuo). During the heating cycle, almost the entire amount of VM&P Naphtha is recovered. The following formula is considered to represent the predominant portion of the ester:

The above finished ester is then compounded with hexadecyl stearate and Dowicide 1, for example:

Percent Finished ester 49.87 Hexadecyl stearate 49.88 Dowicide No. I 00.25

EXAMPLE II Armosul-18-(a-sulfostearic acid-3800 g. (10.00 moles) Hexadecyl alcohol-2460 g. (10.00 moles) VM&P naphtha6-26 g.

Diethanolamine1200 g. (11.40 moles) The process of Example I was followed to produce'the amine salt of the sulfo-ester after which compounding of the finish composition was completed by adding about an equal amount of butyl stearate and a preservative.

7 EXAMPLE 1n Armosul 183800 g. (10.00 moles) Hexadecyl alcohol-2460 g. (10.00 moles) VM&P Naphtha6260 g.

T riethanolamine-1698 g. (11.40 moles) The process of Example I was followed to produce the amine salt of the sulfo-ester and the finish composition.

EXAMPLE IV Armosul 16345 g. (1.00 mole) Groco 54 (Stearic Acid)-265 g. (1.00 mole) Hexadecyl alcohol-484 g. (2.00 moles) VM&P naphtha-4094 g. Diethano1amine105 g. (1.00 mole) The process of Example I was repeated, obtaining the final finish composition in a one-step operation. Dowicide 1 was added as a preservative after the removal of the solvent.

EXAMPLE V Armosul 16345 g. (1.00 mole) Tridecyl alcoho1200 g. (1.00 mole) VM&P naphtha-590 g. Diethanolamine-l20 g. (1.40 mole) The Process of Example I was followed to produce the amine salt of the sulfo ester after which compounding of the finish composition was completed by adding about an equal amount of tridecyl myristate.

EXAMPLE VI Armosul 18380 g. (1.00 mole) Decyl alcoholl 60 g. (1.00 mole) VM&P naphtha-626 g.

N-aminoethyl ethanolamine-IOS g. (1.00 mole) This example demonstrates the diiferences in smoking and volatility between a conventional spin finish and the composition of the present invention.

The conventional spin finish utilized had the following composition in parts by weight.

White mineral oil 66% Degraded triglyceride 18 /3 Potassium soap of a high fatty acid 5 Sodium sulfate salt of an isopropyl ester of oleic acid The finish composition of the present invention corresponded to the product of Example I.

The following results were obtained:

Conventional Present finish invention Smoke point, F 154 216 Volatility at 221 F. (percent) 5. 4 Volatility at 392 F. (percent loss after 4 hrs.) 36. 70 ll. 07

l Keeps volatillzing indefinitely.

EXAMPLE VIII In this example, the following reactants were used:

Armosul 16-173 g. (0.50 mole) Lipal 6TD (ethoxylated tridecyl alcohol-236 g. (0.50

mole) VM&P naphtha179 g.

Diethanolamine==55 g. (0.52 mole) The first three reactants were charged into a 3-neck flask fitted with agitator, thermometer and Dean-Stark trap attached to a reflux condenser. The mix was warmed to a maximum temperature of 127 C. and held at this temperature for one-half hour. At the end of this time, 9 cc. of water were collected in the trap. The free organic acidity was 0.5%. The reaction was cooled to 50 C. and the required amount of diethanolamine for neutralization was added. The Dean-Stark trap was replaced with a downward condenser for the purpose of recovering the solvent. The mixture was heated to a maximum temperature of 175 C. and during the heating cycle, 152 grams of VMP Naphtha were recovered. This ester may then be compounded in various ways, for example:

Percent A B C Ester (Example VIII) 50. 0 50. 0 50. 0 Hexadecyl stearate- 50. 0 25. 0 But-yl stearate 25. 0 50. 0

Total 100. 0 100. 0 100. 0

The above ratio of esters is not to be implied as a limitation. Mixes A, B and C form stable 10% emulsions in water at 50 C. in addition to being clearly soluble in Varsol, e.g. 50/50 ratio.

EXAMPLE IX The first three reactants were charged into a 3-neck flask equipped with agitator, thermometer and a Dean- Stark trap attached to a reflux condenser. The mix was warmed to reflux at 116 C. and held until approximately one (1) mole of water was collected in the trap. Actually 34 grams of water was distilled over. The free organic acidity at this point was 0.3% calculated as oleic acid. The mix was cooled to C. at which point the 210 grams of diethanolamine were added. The Dean- Stark trap was replaced with a distillation condenser and the mix was heated to C. in order to remove the solvent. 600 grams of solvent were recovered, after which the mix was then cooled to room temperature.

By the above reaction, an ester was obtained that was clearly soluble in water at 65 C. in all proportions. However, on cooling, solutions above 40% concentration of the ester formed clear pastes. For use as a lubricant, the above ester was cut to 40% concentration with water at 65 C. On cooling, the said solution is a clear, viscous liquid.

EXAMPLE X In this example, the following reactants were used:

Armosul 16--690 g. (2.0 moles) Carbowax 400400 g. (1.0 moles) VM&P Naphtha-750 g. Diethanolamine2l0 g. (2.0 moles) The reaction is run in the same manner as Example IX and reflux was reached at 113 C. and to obtain the necessary amount of water it was necessary to continue heating until a temperature of 121 C. was reached. 36 cc. of water were collected in the trap and the free organic acidity was less than 1%. The reaction was cooled as above and neutralized with diethanolamine.

The solubility of the above ester was similar to Example No. l. A 40% solution in water at 65 C. becomes a clear viscous liquid on cooling.

When the finished esters of Examples IX and X were compounded into mixes A, B and C of Example VIII, the resultant finish compositions were stable.

EXAMPLE XI A product consisting of 50% of the finished ester of Example I and 50% of polyethylene glycol 400 monolaurate had the following analysis:

25% solution at 50 C Clear, Compatibility test:

80 parts product, 20 parts butyl stearate 1 80 parts product, 20 parts white mineral oil (viscosity at 100 F. (S.U. S.)-=50-60 secs.) Viscosity at 100 F. (S.U.S.) 31 ECS- stable solution.

The alpha-sulfomethylmyristate, ethoxylated alcohol and 154 lbs. of diethanolamine were charged into a vacuum reactor. Full vacuum was applied (50 mml.) without heating until the water and free methanol present in the alpha-sulfomethylmyristate was removed. The foaming of the reaction mass was controlled by bleeding in air through the relief valve. Once the foaming had stopped, all valves were completely closed and the reaction mix transesterified by heating to a maximum temperature of 125 C. until 550 lbs. of methanol were distilled from the reaction mix. The vacuum was then released, and the product cooled to 70-75 C.

The finished ester after further neutralizing with 313 lbs. of diethanolamine was 3,171 lbs., and compounded as under mix A of Example VIII was found to form stable 20% aqueous emulsions, in addition to being clear- 1y soluble in Varsol, e.g. 50/50 ratio.

EXAMPLE XIII This example shows the application of the finish composition of Example XII to a tire cord yarn by the roller method. The finish composition of Example XII was evaluated by a major fiber producer as a nylon 66 tire cord finish. The finish was applied from a aqueous emulsion by roller application. The emulsion was prepared by adding the required amount of finish composition of Example XII to water maintained at 50 C. with moderate agitation. The emulsion was placed in a finish trough in which an application roll rotates. The yarn after extrusion from the spinneret and before drawing passes over the application roll picking up the finish emulsion. In this test, approximately 6% of the emulsion was picked up by the yarn to provide a finish add-on of 0.9%. The results of an evaluation of the finish composition of Example XII as a Nylon 66 tire cord finish is as follows:

Draw twistingExcellent Filament cohesionExcellent Yarn propertiesBetter than standard Coefficient of friction:

Cold0.20 Hot0.25 Elongation at break (460 F.)Over 38% 10 Cohesion (dip adhesion)-32-33 lbs. Process cord strength-3% increase over standard Static (millivolts)- The standard in this evaluation was a Nylon 66 tire cord yarn finished with an ethylene oxide sorbitol monolaurate. Static (millivolts) for the standard was 500.

Various modifications of the compositions and method of the invention may be made without departing from the spirit or scope thereof, and it is to be understood that the invention is to be limited only as defined in the appended claims.

We claim:

1. A finished composition for imparting lubricating and antistatic properties to synthetic fibers consisting essentially of (1) an amine salt of a carboxylic acid ester of an a-sulfonated fatty acid having 8 to 22 carbon atoms in the acid moiety, the alcohol portion of the said ester being selected from the group consisting of alkanols of 1 to 22 carbon atoms, polyethylene glycols having 2 to 205 ethylene oxy groups, alkylene polyols of 2 to 8 carbon atoms and fatty alcohols of 8 to 22 carbon atoms ethoxylated with l to 205 moles of ethylene oxide and the amine being selected from the group consisting of alkanolamines, alkyl amines and polyalkylene polyamines of 2 to 5 amino nitrogen atoms and 2 to 22 carbon atoms and (2) a high molecular Weight fatty acid ester having 8 to 22 carbon atoms in the acid moiety and 1 to 22 carbon atoms in the alcohol moiety and a minimum total carbon atom content of 22 in a salt to ester ratio of 1:99 to 99:1.

2. A composition of claim 1 wherein the ratio of amine salt to fatty acid ester is between 75:25 to 25 :75.

3. A composition of claim 1 wherein the amine salt is the diethanolamine salt of a carboxylic acid ester of ethoxylated tridecanol and u-sulfopalmitic acid and the fatty acid ester is hexadecyl stearate.

4. A composition of claim 1 which also contains up to 5% by weight of the composition of a bactericide.

5. A composition of claim 1 wherein the amine salt is the diethanolamine salt of a carboxylic acid ester of decanol and a-sulfopalmitic acid and the fatty acid ester is hexadecyl stearate.

6. A composition of claim 1 wherein the amine salt is the diethanolamine salt of a carboxylic acid ester of hexadecanol and a-sulfostearic acid and the fatty acid ester is hexadecyl stearate.

7. A composition of claim 1 wherein the amine salt is the triethanolamine salt of a carboxylic acid ester of hexadecanol and a-sulfostearic acid and the fatty acid ester is butyl stearate.

8. A composition of claim 1 wherein the amine salt is the diethanolamine salt of a carboxylic acid ester of tridecanol and a-sulfopalmitic acid and the fatty acid ester is tridecyl myristate.

9. The composition of claim 1 wherein the amine salt is the N-aminoethylethanolamine salt of a carboxylic acid ester of decanol and a-sulfostearic acid and the fatty acid ester is iso-octyl palmitate.

10. A method of imparting lubricating and antistatic properties to synthetic fibers which comprises applying to synthetic fibers after spinning and before heat drawing 0.1 to 5.0% by weight of the fiber of a finish composition of claim 1.

11. The method of claim 10 wherein the finish composition is diluted to a concentration of 1 to 25% by weight with a solvent selected from the group consisting of water and petroleum solvent.

12. The method of claim 10 wherein the finish composition is applied by the roll method.

13. The method of claim 10 wherein about 0.9 to 1.0% of the finish composition is applied.

14. The method of claim 10 wherein the finish composition contains up to 5% by weight of a bactericide.

15. The method of claim 10 wherein the amine salt is the diethanolamine salt of a carboxylic acid ester of 11 ethoxylated tridecanol and a-sulfopalmitic acid and the fatty acid ester is hexadecyl stearate.

16. The method of claim 10 wherein the amine salt is the diethanolamine salt of a carboxylic acid ester of decanol and a-sulfopalmitic acid and the fatty acid ester is 'heXadecyl stearate.

17. The method of claim 10 wherein the amine salt is the triethanolamine salt of a carboxylic acid ester of hexadecanol and u-sulfostearic acid and the fatty acid ester is butyl steal-ate.

18. The method of claim 10 wherein the amine salt is the-'N-aminoethylethanolamine salt of a carboxylic acid ester of decanol and a-sulfostearic acid and the fatty acid ester is iso-octyl palmitate.

19. The method of claim 10 wherein the amine salt is the diethanolamine salt of a carboxylic acid ester of hexadecanol and tx-sulfostearic acid and the fatty acid ester is hexadecyl stearate.

20. The method of claim 10, wherein the amine salt is the diethanolamine salt of a carboxylic acid ester of tridecanol and a-sulfopalmitic acid and the fatty acid ester is tridecyl myristate.

UNITED STATES PATENTS.

2,285,357 6/1942 Robinson 2528.6 2,289,127 7/1942 Koch l 252-8.6 2,325,489 7/1943 Eaton 2528.75 2,865,855 12/1958 Chandler 2,964,470 12/1960 Wentworth 2528.8 3,048,607 8/ 1962 Fareri et a1. 260-401 LEON D. ROS'DOL, Primary Examiner 4 v Y W. E. SCHULZ, Assistant Examiner U.S.'Cl. X.R.'