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Publication numberUS3681244 A
Publication typeGrant
Publication dateAug 1, 1972
Filing dateAug 19, 1970
Priority dateAug 19, 1970
Publication numberUS 3681244 A, US 3681244A, US-A-3681244, US3681244 A, US3681244A
InventorsKimon Constantine Dardoufas, James Edgar Obetz
Original AssigneeAllied Chem
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Finishing composition for multi-filament yarns
US 3681244 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

United States Patent (9 US. Cl. 2528.8 1 Claims ABSTRACT OF THE DISCLOSURE This invention relates to a finishing composition and more specifically to a composition capable of imparting excellent translational efiiciency to high-strength multi-filament yarns. The compositions are particularly suitable for finishing high-strength yarns to be used for the production of tire yarns, conveyor belts, seat belts and the like. The finishing composition comprises the reaction products of polybasic carboxylic acids and polyesters.

These simple esters are obtained by reacting monocarboxylic acid with a polyhydroxy alcohol.

BACKGROUND OF THE INVENTION This application is a continuation-in-part of application Ser. No. 607,381, filed Jan. 5, 1967 now abandoned, for Finishing Composition For Multi-Filament Yarns.

This invention is directed to high-strength symthetic multi-filament yarn containing a novel finishing composition and more specifically to a method of improving the translational efiiciency and other characteristics of said yarn by incorporating thereon a finishing composition comprising complex polyesters.

Still more specifically, this invention is directed to finishing compositions comprising complex polyesters as translational-efiiciency agents for high-strength synthetic multifilament yarns and to the products obtained therefrom. Still further, this invention relates to finishing compositions comprising complex polyesters for filamentary synthetic linear polymers including, for example, polyamides, e.g., nylon, polyesters, polyolefins, and other known polymers useful in preparing structures such as ropes, belts, tire cord and the like.

In the manufacturing of yarn filaments including, for example, filaments from linear polymers such as the polyesters and polyamides, the ultimate strength of the yarn can be substantially improved by subjecting the filaments to drawing techniques to increase their molecular orientation. Although the drawing operation may be conducted by various means, the common procedure comprises devices commonly known as feed and draw rolls for advancing the filaments. The filaments are stretched by running the rolls at differential speeds with the degree of drawing depending upon the ratio of the peripheral speeds of said rolls. In order to localize the point at which the stretching or drawing occurs, a device is placed between the feed and draw roll which is known as a draw pin around which the yarn is wrapped. This pin introduces a frictional drive on the moving filaments which causes drawing to take place in areas of the pin. It is 'well known that the drawing operation can be facilitated when the temperature of the yarn is elevated. The application of heat may be accomplished by various means, e.g., hot plate, etc., placed between the feed and draw rolls, or in the alternative, by using a heated feed roll. It is common practice to employ hot-drawing techniques, particularly when the yarn being processed is to be used for the preparation of products which require high-tensile 3,681,244 Patented Aug. 1, 1972' strengths, as, for example, in the manufacture of tire cord, transmission belts, cable structures, etc.

One of the problems encountered during drawing either at ambient or elevated temperatures is the frequent occurrence of filament breakage. Thus, during drawing, one or more of the individual filaments of the thread line may break and wrap around the draw rolls or the entire thread line may break which requires stoppage until adjust ments can be made. One of the causes of filament breakage during the drawing process, is the buildup of an extensive amount of tension on the yarn which, in turn, is due for the most part to the interfilamentary friction and yarn-to-metal friction. Excessive tensions resulting from the development of high frictions during the drawing can be reduced, however, by applying to the yarn various antifriction compositions. These compositions are generally applied via an aqueous medium prior to drawing. Although there are presently available various finishing compositions which may be used to reduce excessive yarn tension buildup during drawing, there is still, nevertheless, a need for compositions capable of not only lowering the interfilamentary friction, but also for improving the translational-efiiciency and coning efliciency of the yarns.

Thus, it has been found in accordance with this invention that certain complex polyesters are highly effective in obtaining high-strength yarns during orientation of the filaments. These compounds impart good winding and coming characteristics to the yarn and minimize loss of high-strength properties occurring during tensilization which is required of yarns to be used in the production of tire cord and the like. Moreover, the finishing compositions comprising the complex polyesters are relatively unaffected by conventional dyeing operations, thereby imparting permanent low frictional properties to the yarns with the added advantage of eliminating the slashing and sizing operations.

Accordingly, it is an object of this invention to provide a finishing composition comprising a translational efficiency agent which imparts good winding and coning characteristics and minimizes the loss of high-strength properties occurring during tensilization or other stretching treatments applied to high-strength yarns.

It is another object of this invention to provide highstrength multi-filament synthetic yarns having a dynamic filamentary frictional force of between and 300 grams and a static filamentary frictional force of between 280 and 400 grams, wherein there is at least a SO-gram difference between the dynamic and static frictional forces.

It is another object of this invention to provide a permanent finishing composition for synthetic yarns which improves the translational-efficiency and the coning-efiiciency of the yarns.

It is still another object to provide a method of improving the translational-efficiency and the coning-efiiciency of synthetic high-strength yarns, e.g., nylon, by applying thereon a finishing composition comprising the complex polyesters of this invention.

It is still a further object of this invention to provide a finishing composition which is readily emulsifiable and has sufiicient permanency that it survives conventional scouring and high temperature treatments sulficient to impart to the filaments lubricity and low interfilamentary friction so as to improve the fatigue life of the final product.

These and other objects of the invention will become apparent from a further and more detailed description of the invention as follows:

More particularly, this invention relates to a finishing composition comprising at least one complex polyester herein referred to as translational-efficiency agents, either alone or in combination with conventional lubricants,

3 emulsifying agents, antistatic agents, Wetting agents, antistat-emulsifiers and the like.

The finishing composition comprising the translationalefiiciency agents of this invention are compounds characterized by the general formulae selected from the group consisting of wherein R and R are the same or different organic radicals of at least 3 carbon atoms and more preferably, 3 to 32 carbon atoms, selected from the class consisting of aliphatic, or alicyclic radicals derived from alcohols having 3 to 8 hydroxyl groups and aliphatic, with N and N being the same or a different organic radical of a monocarboxylic acid having 16 to 36 carbon atoms; R being a hydrocarbon radical either saturated or unsaturated, and more preferably unsaturated radicals having 2 to 16 carbon atoms, and X being a whole number having the value of 2 to 7; Forlrfiula HOlzizC H2 CH HOHZO CHzOH l onion a 011113 00011 Thus, in the above formulae R and R may be the same or different radicals 'of polyalcohols which can be reacted, e.g., esterified, with N or N which also may be the same or a different radica of a monocarboxylic acid. The simple polyesters obtained by the reaction of the polyhydroxy alcohols, as illustrated above, are complexed or coupled with a dibasic carboxylic acid or their anhydrides which may be either a saturated or unsaturated dicarboxylic acid having 2 to 16 carbon atoms. Examples of such complexing or coupling dicarboxylic acids or their anhydrides include maleic, adipic, azeleic, sebacio etc. up to and including acids having 116 carbon atoms. Examples of compounds corresponding to Formula I include bis(anhydro-enneaheptitol-tristearate) maleate, bis- (anhydroenneaheptitol tristearate) azelate, 'bis(pentaerythritol-tristearate) maleate and bis(pentaerythritoltristearate) azelate. Examples of compounds corresponding to Formula II include anhydro-enneaheptitol-tristearate maleate, anhydroenneaheptitol tristearate azelate, pentaerythritol-tristearate maleate and pentaerythritol tristearate azelate. And examples of compounds corresponding to Formula III include anhydro-enneaheptitol-tristearate and pentaerythritol-tristearate. For example, in the preparation of the simple and complex esters, used as the translational-efiiciency agents of this invention, a polyhydroxy alcohol, such as anhydroenneaheptitol may be reacted with 3 mols of stearic acid to obtain anhydroenneaheptitol-tristearate and 3 mols of water. The tristearate may be further esterified or coupled with the anhydride of maleic acid to obtain bis(anhydroenneaheptitol tristearate) maleate. The reaction of this invention may be illustrated by the following equations; however, it should not be considered as a limitation of the invention as many apparent variations of which are possible without departing from the teaching, spirit or scope thereof.

0 ll OH 01711135 OC (i3 CHZO C17H35 A can C17H C-OC l CH OH III 2 H;

Auhydroenneaheptitol Tristearate bis(Anhydroenneaheptitol Tristearate) Maleate defined above, with X being a whole number having a value of 2 to 8.

It is obvious, for example, that in the preparation of the simple esters and the formation of the complex esters with the dibasic acid, it is possible by varying the proportions of the reacting constituents to obtain mixtures wherein in addition to the main reaction product as illustrated by the above-described reaction, various amounts of side products including anhydroenneaheptitol-tristearate and the half ester of the dibasic acid and the tristearate may be present in the reaction mixture. This mixture or blend of the simple polyester, i.e., the tristearate, with the complex ester, i.e., the ester of the dibasic acid and/ or the half esters thereof, may be used in accordance with this invention to give results similar to that obtained by using the main reaction product or complex ester, as illustrated above and by the following specific compounds.

Anhydroenneaheptitol Tristeaiate Maleate Compound II (A) I Hz 11 a Pentaerythritol Tristearate Maleate Reaction product of hydroxy-ethyl ethyleneamine and urea esterified with stearic acid and coupled with maleic anhydride.

By varying the proportions of the reactants, i.e., the dibasic acids, with the simple polyesters, it is possible to obtain various mixtures of the compounds illustrated by Formulae I(A), II(A), III(A), IV(A) and V(A). The mixtures may comprise, for example, up to about 94% of the simple polyester, e.g., pentaerythritol-tristearate, with the remainder comprising various amounts of the half-ester of the dibasic acid (e.g., Formulae I(A) and II(A)), and/or the complete ester of the dibasic acid (e.g., Formulae III(A) and IV(A)). For purposes of this invention, it is only important that at least about 6% and preferably 10 to by weight of the reaction mixture comprise any one or more of the coupled or complex compounds illustrated by Formulae 1(A) through V(A).

In addition, as illustrated by the above equations, it is obvious that in lieu of the polyhydroxyalcohols, other polyamines and hydroxy-substituted polyamines having 3 to 8 amine groups may be reacted with the monocarboxylic acid, e.g., stearic acid, to form the corresponding amide or hydroxy-substituted amide.

As shown by the Formulae I, II and III, N and N may be either the same or different radicals of monocarboxylic acids having 16 to 36 carbon atoms. These longchain saturated acids may have melting points ranging from about 45 C. to 100 C. Alternatively, unsaturated or branched chain acids may be employed, but then it is preferred that there be at least 20' carbon atoms in the molecule with the melting points of the branched or unsaturated alcohols being greater than about 30" C. Referring to Formulae I, II and III, typical examples of the monocarboxylic acids may include compounds such as palmitic acid, margaric acid, stearic acid, nondecylic acid, arachidic acid, behenic acid, and tricoceric acid, lignoceric acid, pentacosic acid, montanic acid, melissic acid, dotriaconoic acid, hexatriconoic acid, erucic acid, eleostearic acid, and octadecatrieneoic acid. The acid halides, ester and anhydride derivatives of the aboveidentified monocarboxylic acids may also be employed in securing the desired radicals of monocarboxylic acids in the compounds of the formulae.

The relative proportion of the monocarboxylic acids (radicals N and N with respect to the polyhydroxy alcohols (radicals R and R depends upon the particular reactants used to form the corresponding polyesters or polyamides, etc. However, the proportions are such that at least one of the hydroxyl of the polyhydroxy alcohol, remains free and available for reaction or coupling with the carboxylic groups of the dibasic acids.

The polybasic acids may have 2 carbon atoms and preferably from 4 to 16 carbon atoms and are either saturated or unsaturated dicarboxylic acids which, when reacted with the simple esters, result in products having melting points ranging from 30 C. to C. and more preferably, from 30 C. to 100 C.

It was found that as the ratio of the dibasic acid was increased with respect to the simple polyesters, the highstrength translational-efiiciency and cold temperature adhesion properties in the yarn reached a maximum. Thus, for example, optimum results were obtained with ratios of one mol of the dibasic acid to 1.3-4.0 mols of the simple polyesters. A specific preferred ratio, however, is approximately one mol of the dibasic acid for two mols of the simple polyester. Good performances with the translational-efiiciency components were obtained, however, when the components Were prepared by utilizing 1 to 16 mols of the simple polyester per mol of the dibasic acid. With these ratios, the final product may be a mixture of the coupled or complex esters with large amounts of the uncoupled polyesters.

Of the various polyhydric alcohols which may be used for preparing the compounds of this invention, the preferred include anhydroenneaheptitol, pentaerythritol, dipentaerythritol, pyranose, etc. Other polyhydric alcohols include the neopentyl alcohols, e.g., trimethylolethane, trimethylolpropane, trihydroxybutane, 1,2,6 hexanetriol, desoxyanhydroenneaheptitol, etc. The alicyclic compounds may include cyclohexanehexol, 1,2,4 trihydro-xycyclohexane, etc. In place of the polyhydroxy alcohols used in preparing the simple polyesters, the polyamines that may be used include compounds such as polyethyleneimine and various heterocyclic nitrogen compounds such as the melamines, ammeline, ammelide, and various cyclic nitrogen compounds such as the guanamines, more specifically adipoguanamine, which may be substituted with one or more hydroXyl groups. The hydroxy-substituted amino compounds may include, for example, hydroxymethyl (aminomethyl) methane and the various analogs of pentaerythritol, such as tetrakis (aminomethyl) methane and tetrakis (carbomido methyl) methane, 3-triamino pyrimidines, etc.

In preparing the high-strength multi-filament yarns of this invention, the finishing composition may comprise in addition to the translational-efficiency agent, i.e., the complex esters, other well-known, conventional yarn-treating components comprising lubricants, emulsifying agents, antistatic agents, antistat-emulsifying agents, wetting agents, etc. The translational-eificiency agents of this invention may be used in combination with these other materials in relative proportions illustrated below.

EXAMPLE I.-COMPOSITION RANGES Parts by weight Translatioualelficiency agents- 2 to 20.. 5 to 15. Lubricants 25 to 70 40 to 50. Antistat-emulsifiers 5 to 70..-- 20 to 35. Wetting agents to 20...- 1 to 10.

for example, triesters of Cm-Cw fatty acids, esters of pen- 4.0

taerythritol and lower fatty acids, triglycerides, animal oils, vegetable oils, e.g., corn oil, coconut oil, soybean oil, olive oil, etc, mineral oils having say-bolt viscosities from about 30 to 180 seconds at 180 F, and synthetic lubricants including, for example, the polyalkylene glycols. Other lubricants include the fatty acid esters, e.g., esters obtained from fatty acids having 1 to 22 carbon atoms and monohydric or polyhydric alcohols having 1 to 12 carbon atoms, such as isopropyl palmitate, methyl abietate, isobutyl laurate, glycerol tripropionate, propyl oleate, amyl oleate, isobutyl ricinoleate, glycerol monoricinoleate, dibutyl succinate, so-rbitol tetrastearate, etc. Others include the triglycerides such as, for example, glycerol mono-i ricinoleate diacetate, glycerol monolaurate dibutyrate, glycerol monolaurate divalerate, and the like.

The antistat-emulsifying agents used in combination with the lubricants and translational-efiiciency components of this invention may be present in the finishing compositio in amounts ranging from 5 to 50 parts by weight and, include, oleyl amines, tallow amines, fatty alcohols having 12 to 20 carbon atoms, and alkali metal salts of phosphate esters thereof said amines and alcohols being ethoxylated with about 5 to about 26 moles of ethylene oxide. For example, the polyoxyethylene alkylamines, e.g., tallow amine reacted with 20 mols of ethylene oxide, polyoxyethylene oleyl alcohol, complex oleyl-ethylene oxide sodium phosphate salt (GAF-GB-520), polyoxyethylene glycerolmonooleate (SYN-PAC No. 80), polyoxyethylene castor oil (POMOCO C-ZS), polyoxyethylene oleyl alcohol, sulfated aliphatic polyester of succinic acid, nonyl phenol-ethylene oxide reaction products (IGEPALCO630), arylphenyl polyethoxyethanol, and various amine soaps derived from fatty acids containing at least 8 carbon atoms reacted with water-soluble aliphatic amines, particularly the alkylolamines including,

for example, the fatty acid soap of amines such as triethanol amine, and the like.

The wetting agents, if used, may include polyoxyethylene ethers of long-chain fatty alcohols and the polyoxyethylene esters derived from long-chain fatty acids. The long-chain fatty alcohols and fatty acids from which the nonionic surface-active agents are obtained may contain from 12 to 40 carbon atoms in the alkyl group and may include the straight or branched chains. The fatty alcohols include, for example, dodecyl alcohol, cetyl alcohol, myristyl alcohol, mixtures thereof, etc. The acids may include, for example, oleic acid, lauric acid, mixtures thereof, etc. These particular nonionic surfactants are also desirable components of the finishing composition in that they tend to suppress any accumulation of static during the drawing operation in addition to providing emulsion stability.

In applying the finishing composition of this invention to the filaments, e.g., nylon, conventional methods may be employed. In general, good results are obtained in both hot and cold drawing operations when the finishing compositions, e.g., comprising a lubricant, etc., are applied in amounts ranging from about 0.01 to 2.0% and more preferably 0.2 to 1.5 by weight of the yarn. The finishing compositions are applied to the filaments or yarn prior to drawing by conventional and known techniques which comprise, for example, bringing the yarn in contact with the composition while it moves during the course of production. The composition may be applied to the yarn by various methods and devices which may include the use of a wick, split-roll or by having the yarn pass through a bath containing the finishing composition.

The amounts of each of the components of the finish with respect to the weight of the yarn are more specifically shown in the following example.

EXAMPLE [I Percent ranges of each component 1 Translationalcfiiciency agent, e.g., anhydroenneaheptitoltristearate maleate 0.01-0.6 0.03-0.11 Lubricant, e.g., coconut oil 00. 7 0. 04-0. 7 Antistat-emulsifier, e.g., ethoxylated castor oil 0-0. 7 0. 054). 7 Wetting agent, e.g., ethylene oxide-alkyl phenol products 00.4 01-(14 Based on weight; of yarn.

The filamentary materials to be treated with the finish compositions of this invention may be prepared from synthetic linear polymers such as the polyamides or polyesters, and blends of the polyamides and polyesters, as more specifically disclosed in copending application Ser. No. 368,028, filed on May 18, 1964. (Belgian Pat. No. 661,784).

In preparing continuous filaments of yarn for subsequent fabrication into ropes and the like, the yarns, for example, are given a slight twist, e.g., one-half turn per inch. Ropes, belts and the like are prepared from these yarns by a multi-stage process, the steps of which may vary depending on the type of rope or belt desired. In general, however, the process comprises forming strands by laying together a plurality of yarns, for example, 70 to 80, in a lefthand direction, i.e., with an S or lefthand twist. The next step involves plying the desired number of these strands, e.g., three or more, to form a rope with a Z twist or right lay in which the previously imparted twists are lost, and on occasion, additional twisting is produced. This procedure results in a finished rope of linear structure composed of a limited number, usually 3 to 9, of twisted strands which are made up of a plurality of plies of twisted yarns, and in which the yarn is made up of a plurality of continuous filaments.

The following tables particularly point out the improvement realized by using the finishing compositions of this invention on multi-filament yarns.

TABLE I Percent solids deposited on the yarn Description Range Preferred Total solids finish deposited on the yarn .25 to 1.5-..- .5 to 1.0. High translational efiiciency agent or component. .02 to .2 .05 to .11. Lubricant .04 to .7 .21 to .43. Emulsifier-antistat 0.05 to 0.70. .1 to .5. Wetting agent .005 to .04--- .01 to .03.

Percent pickup finish emulsion High strength yarns 3.0 to 8.0--.- 4.0 to 6.0. Textile yarns 4 to 14 6 to 13. Fine denier yarns 7 to 14 10 to 13. Percent solids content of emulsion to 40""... to 20.

Frictional properties of high-strength yarns: Grams Dynamic frictional properties 140 to 300- 180 to 260. Static frictional properties 280 to 400...- 300 to 350. Differential between dynamic and static,

minimum. 50 80 to 120. Yarn-to-metal frictional properties 120 to 320...-

The data in Table I with regard to the yarn-to-metal friction was measured on 840 denier yarn, travelling at 1,000 ,feet per minute over a No. 62 metal pin measured by 28 grams pretension. Other means of determining the yarn-to-metal frictional forces can be found in Textile Research Journal by Schlatter, Olney & Baer, volume 29, pages 200-210, March 1959. In brief, the method employed uses a Brush Tension Analyzer whereby the yarn is passed at a speed of 1000 feet per minute with one turn over a polished stainless steel pin of surface finish of root mean square of 3.0 microinches giving a metal-to-yarn angle of 360 against a floating pretension weight of 28. grams. A chart reading shows a constant tension which is a measurement of the yarn-to-metal frictional forces.

The yarn interfilament frictional forces are measured by using a Brush Tension Analyzer Model ED-13-403 (Brush Electronics Company, Cleveland, Ohio), whereby the yarn is passed at a speed of 1 cm./minute over pulleys positioned so that the two strands under test which are twisted one and one-half turns running against each other act an imposed helix arc of 360 with a positive tension of 600 grams. The frictional forces imposed are measured on the apparatus strain gauge and recorded on a typical continuous recording chart. The chart frictional pattern show-s a gradual increase in tension until the static friction is overcome. Subsequently, there is a rapid drop in tension until a level is reached where the dynamic friction overcomes the imposed tension. Thus, the chart reads in a zig-zag pattern showing a continuous series of low frictional measurements and gradual rise with sudden drops in friction and, hence, the name slip-stic friction.

At the lower yarn-to'metal frictional properties, e.g., below 120 grams, there is a tendency to get slippage in the drawing of the high strength yarns, whereas at the high yarn-to-metal frictional forces, e.g., above 320 grams, there is a tendency to get a large number of breaks and wraps with abrasion of the guides and equipment. Of the yarn friction-a1 forces for high strength yarns, it is important to have low interfilamentary frictional forces which are of greater significance than the yarn-to-metal frictional forces. For example, as the dynamic frictional forces reach 260 grams and go beyond 300 grams and as the static frictional forces reach 350 and go beyond 400 grams, the improvement in the final strength of the tensilized cord, e.g., stretched seat belts, is considerably reduced. Moreover, if the yarn drops below grams differential between the static and dynamic frictional properties, it is not possible to obtain satisfactory coning. In actual practice, it is preferred to have at least grams minimum differential between the static and dynamic frictional forces in order to obtain optimum coning performance.

Thus, since it is diflicult to obtain low interfilamentary friction-a1 forces and still maintain a relatively high differential between the static and dynamic frictional forces, it was unexpected to find that the finished compositions of this invention provided this property for high strength yarns.

The following data in Table II and Table IIA (contained on subpages 1-8) shows the improvement of the compositions of this invention in comparison to known materials used heretofore.


Finish pickup Yarn- Greige cord Tensilized cord (Breaks/ Yarn to-metal wraps denier (Dynamic/ Per- Ex; Foot- Parts by wt., Over-all drawing (UTS static yarncent B5,! B8,! Adhes.,# No. note finish comp. perform. perform.) (instron)) Coning to-yarn) ET7 lbs. ET7 lbs. E'l armstr.

Min. oil sec,

1 (2) f j 4.75% (1 3 842 (8.3) P0012... 250 250 250 92.6 44.6 96.5 44.2 95.7 17.7

AC-680 (PE Wax),

Coconut oil, 7.40-.-- Erml-antistat, 2 (1) f 4.83% 840 (8.4 POOL". 275 275 275 89.3 44.0 94.6 43.9 94.4 15.9

( Wetting agent,

9 9 8 fig ifg 3 m: 4 27% o 2 842 s. 4) Poor 260 (260/285) 89 43.6 93.2 44.8 95.7 14.4

( Wetting agent, 0.5

9 a 4 8 3 533 2; G00d... 429% 0 0) 645 (8.3) Good... 253 (254/338) 94.5 46.1 97.6 44.6 96.5 17.3

( Wetting agent, 0.5...

( Coconut oil, 7.5"... (2) Emul'amstamfim Excellent- 4.08% (o 1 839 8.4 Excel- 265 (263/840) 93.0 44.0 94.6 45.6 98.1 16.8

o lent Wetting agent, 0.5.

TABLE IIContinued Finish pickup (Breaks/ 600 gms. Efficiency wraps dynamic] Ex. Foot- Over-all drawing Yarn/metal, static yarn- Transla- No. note Parts by weight, finish composition perform. perform.) Coning 1,000 f.p.m. to-yarn tional Emulsion Min Oil, 60 SSU, 7.0 6 Stearic acid, 1.4..-. Fair /1 Good..... 150 293-532 Poor Emulantistat, 5.6.. Min Oil, 100 SSU, 5.0 7 Cerathane 63, 3.0..- Poor 0/2 loor 0000 190 308-338 Good Emul-antistat, 6.0.. Drew FD-0670, 7.0 Cerathane 63 (hydrocarbon wax), 2.0. 8 Emul-antistat, 5.0 Poor 0/1 Poor 240 300-320 Good Wetting agent, 2.0.. Allied wax 080, 0.5. Coconut oil, 4.0.. 9 Cerathane 63, 3.0. Bad 0/21 Bad 205 260295 Fair (2 Emulantistat, 7.0

Tigigtltycerolficgsmo ester of lower chain a y ac 10 (1) Cerathane 63, 2.0 Poor 0/1 Poor 240 312338 Fair Emul-antistat, 8.5.. (6) Coconut oil, 4.0- 11 1 (J t 3 3 Poor 0/5 Bad 215 240-268 Good*.....

(3) EIfEg-Entlstflt, 7610...-

i c' 3 0- 8 ggi gfifi }Poor o o Good.---- 240 271-379 Fair Fair.

leruci Coconut on {if Fair 0 0 Good 175 262-350 Fair Fair.

(5) Ilgmfiill-an1is1t1at, 8.1 r0 3 g, 5 33i Poor o 1 Good.-- 170 209430 Poor Fair.

(2) gmul-artitisltastb 4.

ocon 1 E2; jg g }Good...-. 0 0 Good 220 187-316 Good--... Good.

(2) gompoigndl lgfo 1.0-. ocon E2; g gg }Excellent. o o Excellent- 22o 224-335 Excellent- Excellent.

gortripoundgIlI, 1.0-. 5 u rica t, .0 E Emumnntismty 7 }Good. 0/0 Good....- 230 174-332 Very good. Excellent.

(2) gonnlgunl Ill 1 1 0.8.

e e 7 2? g t igg' Good"..- 0 0 Good..... 220 191-356 Good..." Good.

0) IC)ompi} u]:r)1d III 6 0 5.-

5 row -0670 E2; E l mt 7 7 GOOd.. 0/0 G0O(l.. 210 265-352 GOOd... Good.

gompoiind Ill/ ..1.6 5 onven iona non-wax ms 1, G d 0 U 2 9 5 23-...{ (1) compound m o 100d 05 1 3 8 6 Good Good Coconut oil, 8.0. 24.. Emul-antistat, 7.5.. Good.. 0/0 GooiL. 240 270-340 Good.-..- Good.

( Compound I, 0.65

1 TEC=PerInanent finish component, e.g., Cerathane 63 (hydro- Lubricant.

WA=Wetting agent (IGEPAL 4 UN: Unsatisfactory, due to poor coniug.

' This invention.

7 ET=Translational cffieieney.

B BS=Breaking stren th.

Order of rating1= 00d; 2=Poorg 3=Fair.

TABLE IIA This Conven- TEC invention, tional tire polyethylene compound yarn C wax, finish, Example 25 Example 26 Example 27 Example 28 Compositions, see Example 2-.-- Example 5-.-- Example 16 Percent pickup 5.0 5.0 Breaks/pound.-. 0.015. 0.000. .016. Wraps/pound-. 0.009. 0.020. .04. Draw ratlo 5.43.- 5.43.- 5.40. Denier..- 1,274- 1,264- 1,270. UE 18.4.- 18.5-- 18.7. UTS, g.p.d 9.3.. 9.3-. 9.04. Toughness index, TE l/2. 40.0.. 30.0.. 39.0. Yarn/metal 1,000 f.p.m. pin 62 300..... 295.... Dynamic/static yarn/yarn, 600 gms. preten- 245/245 239/306 299/430.


Tenacity, gms./den.. Translation efficiency 94% Tensilized cord:

Allied heat stability. Coning B ET greige, ET tensilized, overall transla- 91 tional efficiency. Overall rating 4 Poor* (2) Good (1) Fair (3).

7 4 See footnotes at end of Table II. Order of rating.

It should be noted from the data in Table II that the various examples represent various finish compositions utilizing the preferred components of this invention. When ployed as the finishing composition, excellent results were obtained with respect to coming, translational efficiency, drawing performance, and the ability of the composition the optimum proportions of the components were emto be easily emulsified. Thus, it can be seen from the data in Table II that the finishing compositions of this invention provide high values with respect to the translational efiiciency agent particularly useful for high strength yarns. The translational efiiciency agents used in each of the above examples are particularly characterized by empirical Formulae I-V given hereinabove.

Examples 1, 2, 3, 7, 8, 9, 10, 11, 13, 15 and 26 are conventional finish compositions containing translational efiiciency agents. However, while these finish compositions 14 adhesion properties and exhibit poor coning properties. Examples 6 and 16 illustrate conventional tire yarn finishes which exhibit high interfilamentary frictional properties and, therefore, as a result, their translational eificiency into tensilized tire cord is comparatively poor. Thus, for example, Example 6 has a static interfilamentary frictional force of 532 grams, whereas Example 16 has a static frictional force of 430 grams, both of which are beyond the maximum necessary to achieve good yarn translational have good translational efiiciencies with respect to tensile 10 efficiencies.

TAB LE III Yarn-to- Dynamic/Static Overall yarn yarn-to-yarn transla- Example Drawing frictional frictional tional Emulsion Overall number Finishing component performance properties properties Coning efficiency efiic. perform.

1 Bis (anhydroenneaheptitol) maleate Excellent 265 263/340 Excellent Excellent.... Good..." Excellent.

strength properties, they are, nevertheless, regarded as 20 being less satisfactory than the compositions illustrated for purposes of this invention in that they are either difficult to emulsify or have a tendency to show reduced As noted from the data in Table III, the use of a finishing composition comprising the bis (anhydroenneaheptitol) maleate gave excellent results with respect to coming, trans lational efficiency and over-all performance.

TABLE IVEVALUATION OF 840/136 YARNS BEARING SPIN FINISHES Finish pickup, Yarn-tobreaks/ metal,

wraps (dynarnlc/ Greige cord Tensile cord Overdrawing UTS, static Armst Ex. Foot- Percent all performg.p.d. yarn-to- Tens. BS 5 BS 8 adhes N 0. note Composition pickup rating ance Coning (IP4) yarn) eflic. lbs. ET 7 lbs. ET 1 4. 75 Poor 1/3 Poor 8. 95 250 (250/250) 92. 5 44. 6 96. 5 44. 2 95. 7

4. 27 Poor 0/2 Pooh--. 9. O0 260 (260/285) 89. 1 43.6 93. 2 44. 8 95. 7 14. 4

4. 29 Excel 0/0 Excel.. 9. O5 253 (245/338) 94. 3 45. 1 97. 6 44. 6 96. 5 17. 3

Coconut oil, 7. 5 32 Emul-antist., 7. 5.--- 4.08 Good 0/1 Good- 8. 95 265 (263/340) 93.0 44.0 94.6 45. 6 98. 1 16. 8

Comp. III, 2. 0".-. WA, 0. 5 H2O, 72.5

1 TEC=Permanent finish component, high translational eificiency. 5 Lubricant. 2 EA=Emulsifier-antistat. This invention. 3 WA=Wetting agent. 7 ET=Translational efficiency. 4 UN =Unsatisiactory, due to poor coning. B BS=Breaking strength.

TABLE V Finish Qonven- High translational tional tire eificiency polyethylene yarn finish This invention wax Example Number Finish composition of example Nos. of Table I 6 5 2 2 Pickup Level, percent 4. 5 4.0 4. 5 4.0 4. 5 Good Good Good UTS, g p.d. (IP4) 9. 1 9. 2 9. 1 9. 2 9. 1 Drawing performance- Good Breeks/pound 0.04 0.05 0.02 0. 07 0. 10 Wraps/pound--- 0. 28 0. 21 0.09 0. 22 0. 24 Overall rating 3 2 1 4 5 1 Poor. Fair. 3 Excellent. 4 Fair to good.

TABLE VI Finish of this Polyethylene invention wax Conventional finish Composition of Example Nos 5 2 6 4. 4. 4. 5 4. 5 4. 5 g o UTS, god. 9. 8 9. 8 9. 9 9. 8 9.9 Drawing performance Good Good Good Breaks/pound 0. 02 0. 08 0. 03 0. 03 0. 42 Wraps/pound 0. 09 0.09 0. 02 0.02 03 Overall rating 1 2 3 4 5 1 Poor. 2 Excellent. Bad.

The above data shows the results obtained in spinning polyblends, e.g., 45% polyethylene-terephthalate, and 55% nylon. Example 34 of this invention gave excellent drawing performance at a 4.5% finish pickup level in comparison to conventional yarn finishing compositions. Likewise, the data in Table VI shows that a polyblend of 30% polyethyleneterephthalate and 70% nylon gave outstanding performances in comparison to conventional finishing compositions with respect to drawing performance, coning, and the over-all rating.

the toughness index. Moreover, the instant finishing compositions permit the yarns to be drawn to high breaking strengths without incurring undue breaks and wraps and also improve the adhesion properties with respect to rubber. This is an important characteristic, particularly in the preparation of yarns to be used for tire production. It is believed that the improved adhesion is due to the physical and chemical action of the finishing compositions which may be activated during the tensilization and vulcanization processes to establish a more permanent bond between TABLE VII Percent solids Finish, percent Percent of total on nylon before solids on yarn solids retained scouring after scouring after scouring and mock dyeing and dyeing F'nish com osition of this invention Exam 1e No. 32:

1 Coconu ti oil u? .305 .242 79. 0 TEC component Compound III 08 .078 97.0 Emulsifier-antistat and wetting agent 325 11. 18 34. 5-55. 4

Total finish solids on yarn 71 43-. 5 60-70. 5

Conventional prior art finish composition:

Lubricant (mineral oil 37 0. 10 27. 0 Emulsifier-Antistat 40 0. 10 25. 0

Total finish solids on yarn 77 0. 20 26.0

Seat belts prepared from yarns treated in accordance with this invention containing the finishing composition of Example 32 in Table IV were put through an extensive scouring and mock dyeing test which simulated scouring and extraction conditions more severe than that actually used in typical scouring and dyeing operations. The data obtained from these tests are indicated in Table VII.

It can be seen from the data in the above table that the finishing composition of this invention containing the translational-efiiciency agent possesses unique resistance to scouring and conventional dyeing processes and thereby retains a major part of these properties in future weaving and other textile operations. Moreover, the finished filaments and the articles prepared therefrom have unique abrasion-resistance and as a result thereof, have improved wearing characteristics. For example, after utilizing the finishing compositions of this invention on 840/56 denier yarn and subsequently weaving this yarn into seat belts, it was found that the average break strength of said seat belts ranged between 6800 and 7200 pounds, as compared to the 62006300 pounds breaking strength for yarns employing conventional frictional compositions. Thus, when the finishing composition of Example 5 of Table II was applied to textile yarns in the range of approximately 10% pickup, it was found that a durable finish was obtained, suitable for operation without the subsequent use of a slashing or sizing operation. Consequently, it is obvious that there is considerable economy in the utilization of yarns treated with the compositions of this invention.

As shown by the data in the tables, this invention is particularly concerned with industrial fibers having incorporated thereon a permanent finish composition which imparts thereto low inter-filamentary frictional properties which, in turn, provides improved strength characteristics in the final textile structure. The finishing compositions of this invention remain stable and are nonvolatile during the drawing process and add to the yarn sufiicient lubricity that it can be highly oriented to increase the tensile strength While simultaneously increasing the yarn and the rubber. Thus, because of the improved performances of the finish compositions, they may be used with a wide range of products, thereby avoiding the necessity of having to prepare a multiplicity of finish compositions depending on the dilferent end uses. That is, the finish compositions of this invention are particularly suitable, for example, for the production of high-strength pile yarns, conveyor belting, seat belts, tire yarn and the like.

While this invention has been described with respect to a number of specific examples, it is obvious that there are a number of variations and modifications which can be resorted to without departing from the scope of the invention, as more particularly pointed out in the appended claims.

We claim:

1. A liquid composition consisting essentially of (a) about 2 to about 20 Weight percent of said composition consisting of a mixture of (I) a compound selected from the group consisting of bis(anhydroenneaheptitoltristearate) maleate, bis(anhydroenneaheptitol-tristearate) azelate, bis(pentaerythritol-tristearate)maleate and bis(pentaerythritol-tristearate) azelate, (II) a compound selected from the group consisting of anhydroenneaheptitol-tristearate maleate, anhydroenneaheptitol-tristearate azelate, pentaerythritol-tristearate maleate and pentaerythritol tristearate azelate, and (III) a compound selected from the group consisting of anhydroenneaheptitoltristearate and pentaerythritol-tristearate; the total of compounds I and II in said mixture amounting to at least 6% by weight of said mixture;

(b) about 25 to 70 weight percent of said composition being an oil selected from the group consisting of animal, vegetable and mineral oils; and

(0) about 5 to 50 weight percent of said composition of a compound selected from the group consisting of ethoxylated oleyl amines, ethoxylated tallow amines, ethoxylated oleyl amines, ethoxylated tallow amines, ethoxylated fatty alcohols having 12 to 20 carbon atoms and alkali metal salts of phosphate esters 17 thereof, said amine, and alcohols being ethoxylated with about to about 26 moles of ethylene oxide.

2. The composition of claim 1 as an aqueous emulsion.

3. The composition of claim 1 wherein the mixture consists essentially of anhydroenneaheptitol-tristearate maleate, bis(anhydroenneaheptitol-tristearate) maleate, and anhydr0enneaheptitol-tristearate.

4. The composition of claim 1 wherein the mixture consists essentially of anhydroenneaheptitol-tristearate azelate, bis(anhydroenneaheptitol-tristearate) azelate, and anhydroenneaheptitol-tristerate.

5. The composition of claim 1 wherein the mixture consists essentially of pentaerythritol-tristearate maleate, bis(pentaerythritol-tristearate) maleate and pentaerythriol-tristearate.

6. The composition of claim 1 wherein the mixture consists essentially of pentaerythritol-tristearate azelate, bis (pentaerythritol-tristearate) azelate and pentaerythrioltristearate.

7. The composition of claim 1 having an additional ingredient of about 1 to about 20 weight percent of said composition selected from the group consisting of polyoxyethylene esters of long-chain fatty acids having 12 to 40 carbon atoms.

8. A synthetic filamentary yarn comprised of filaments which are treated with about 0.01 to about 2.0 weight percent based on the weight of the yarn of the liquid composition of claim 1.

9. A synthetic filamentary yarn comprised of filaments 18 which are treated with from about 0.01 to about 2.0 weight percent based on the weight of the yarn of the liquid of claim 7.

10. The synthetic filamentary yarn of claim 8 wherein the vegetable oil is selected from the group consisting of linseed oil, soy bean oil, corn oil, peanut oil, castor oil, coconut oil, rapeseed oil, and olive oil.

11. The synthetic filamentary yarn of claim 8 wherein the filaments are selected from the group consisting of linear polyamides, linear polyesters, and blends of said polyamides and polyesters.

References Cited UNITED STATES PATENTS 2,067,950 1/ 1937 Schneider 252-816 X 2,404,240 7/1946 MacLaurin 252-89 2,480,347 8/1949 Wittcofl 260-3458 2,810,694 10/1957 McLean et al. 252-8.8 3,413,081 11/1968 Wolfl et al. 260-4106 FOREIGN PATENTS 527,483 7/ 1956 Canada.

HERBERT B. GUYNN, Primary Examiner US. Cl. X.R.

ll7-l38.8 B, 138.8 F, 138.8 N, 139.5 F, 139.5 CQ; 252- 8.6, 8.9; 260-3458, 410.6

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3850658 *Feb 5, 1973Nov 26, 1974Allied ChemMultifilament polyethylene terephthalate yarn
US3882168 *Sep 3, 1971May 6, 1975Hoechst AgPhotopolymerizable compounds
US3893929 *Feb 1, 1973Jul 8, 1975Procter & GambleCompositions for imparting renewable soil release finish to polyester-containing fabrics
US3985923 *Jan 17, 1975Oct 12, 1976The Procter & Gamble CompanyProcess for imparting renewable soil release finish to polyester-containing fabrics
US4210700 *Sep 15, 1978Jul 1, 1980Allied Chemical CorporationProduction of polyester yarn
US4442249 *Dec 13, 1982Apr 10, 1984Fiber Industries, Inc.Partially oriented polyester yarn finish
US4617236 *Oct 21, 1985Oct 14, 1986Allied CorporationAdditives to polyester tire yarn overfinish to reduce dip penetration
US6365065Apr 7, 1999Apr 2, 2002Alliedsignal Inc.Spin finish
US6426142Oct 15, 1999Jul 30, 2002Alliedsignal Inc.Spin finish
US6712988Jun 6, 2002Mar 30, 2004Honeywell International Inc.Spin finish
US6770231Oct 26, 2001Aug 3, 2004Alliedsignal, IncSpin finish
US6908579Dec 18, 2003Jun 21, 2005Performance Fibers, Inc.Process for making a yarn having a spin finish
US7021349Sep 3, 2004Apr 4, 2006Performance Fibers, Inc.Spin finish
US20020171061 *Oct 26, 2001Nov 21, 2002Ralf KleinSpin finish
US20040144951 *Dec 18, 2003Jul 29, 2004Alliedsignal Inc.Spin finish
US20050142360 *Sep 3, 2004Jun 30, 2005Ralf KleinSpin finish
U.S. Classification428/395, 554/106, 252/8.82, 554/227, 252/8.86, 549/420, 252/8.84
Cooperative ClassificationD06M7/00, D06M2200/40
European ClassificationD06M7/00