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Publication numberUS3914177 A
Publication typeGrant
Publication dateOct 21, 1975
Filing dateApr 22, 1974
Priority dateMar 22, 1972
Publication numberUS 3914177 A, US 3914177A, US-A-3914177, US3914177 A, US3914177A
InventorsBernholz William F, Nahta Roop, Redston John Percy, Warman Murray
Original AssigneePvo International Inc
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Hydroxy pivalyl hydroxy pivalate esters and method of treating textile filaments therewith
US 3914177 A
Abstract
The disclosure is directed to hydroxy pivalyl hydroxy pivalate esters, to textile finishes therefrom, and to the method of applying these finishes to synthetic linear organic polymer filaments. For example, the hydroxy pivalyl hydroxy pivalate mixed diester of capric, lauric, myristic, palmitic, stearic, and oleic acids in an aqueous emulsion may be used as a finish for thermoplastic fibers.
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United States Patent [1 1 Nahta et al.

[ Oct. 21, 1975 [54] HYDROXY PIVALYL HYDROXY PIVALATE ESTERS AND METHOD OF TREATING TEXTILE FILAMENTS THEREWITH [75] Inventors: Roop Nahta, Nutley; William F.

Bernholz, Wayne; John Percy Redston, Montclair; Murray Warman, East Brunswick, all of NJ.

[73] Assignee: PVO International Inc., San

Francisco, Calif.

[22] Filed: Apr. 22, 1974 [21] Appl. N0.: 462,744

Related US. Application Data [63] Continuation-in-part of Ser. No. 236,963, March 22,

1972, abandoned.

[52] US. Cl. 252/8.8; 252/8.6; 252/8.9;

260/484 A; 428/290; 428/480 [51] Int. Cl. D06M 13/16 [58] Field of Search 252/8.6, 8.8, 8.9;

[56] References Cited UNITED STATES PATENTS 3,113,369 12/1963 Barrett et al 252/8.6 X 3,428,560 2/1969 Olsen 252/8.6 X 3,441,953 4/1969 Dumont et a] 260/484 X 3,464,922 9/1969 Bernholz et al 252/8.6 3,644,143 2/1972 Flett 252/8.6 X

Primary ExaminerMurray Tillman Assistant ExaminerT. DeBenedictis, Sr. Attorney, Agent, or Firm-Owen, Wickersham & Erickson [57] ABSTRACT 21 Claims, N0 Drawings HYDROXY PIVALYL HYDROXY PIVALATE ESTERS AND METHOD OF TREATING TEXTILE FILAMENTS THEREWITH This is a continuation-in-part of our prior copending application Ser. No. 236,963, filed Mar. 22, 1972 now abandoned. The present invention relates to finishes for filaments of synthetic linear organic polymers. The present invention further relates to a method of applying these finishes to synthetic linear organic polymer filaments.

Synthetic linear organic polymers, for example, polyamides such as nylon as well as polyester are commonly formed into filaments by the process of melt-spinning, and the resultant filaments are drawn in the solid state in order to develop a high degree of tenacity so that they become suitable for textile purposes. To facilitate the drawing of the filaments and other textile processing to which they may be submitted, it is necessary to apply a finish to the newly melt spun material, in order to reduce friction during passage of the filaments over metal surfaces in textile machinery. Such reduction in coefficient of friction between the fiber-to-metal surfaces prevents filament abrasion. The finishes must be capable of lubricating the filaments so that they do not break during drawing. In the case of multifilament yarn it is furthermore necessary that the finish provide some degree of balanced cohesion between the constituent filaments of the yarn. This cohesion is particularly important in flat warp knitting. It is also very desirable that the finish have a high degree of oxidation resistance, including resistance to both discoloration and formation of insoluble resinous or polymeric compounds. It is further desirable that the finish exhibit high temperature stability and resistance to smoke generation at temperatures encountered during the processing of the synthetic linear organic polymer filaments. These latter characteristics are particularly applicable to the hot stretching operation used during the production of synthetic linear organic polymers.

It is an object of the present invention to provide finishes for filaments of synthetic linear organic polymers.

Another object of the present invention is to provide finishes for filaments of synthetic linear organic polymers to reduce the coefficient of friction between fiberto-metal surfaces.

A further object of the present invention is to provide finishes for filaments of synthetic linear organic polymers to provide balanced cohesion between the fiberto-fiber surfaces.

A still further object of the present invention is to provide finishes for filaments of synthetic linear organic polymers that exhibit thermal stability and resistance to smoke generation, particularly during hotstretch processing to orient the polymer in order to obtain maximum uniformity of tensile strength, such as in nylon and polyester tire cord production.

A still further object of the present invention is to provide a method of applying finishes to filaments of synthetic linear organic polymers.

A further object is to provide an improvement in the manufacture of filaments and yarns of synthetic linear organic polymers by treating such filaments or yarns with a finishing composition having lubricity and resistance to oxidation and discoloration at elevated temperatures.

A further object is to provide a tire yarn lubricating composition which will lead to high temperature processing continuity, and yield polyester tire cords having excellent adhesion to rubber and a high resistance to flex fatigue.

The above objects and still further objects of the invention will immediately become apparent to those skilled in the art after consideration of the following preferred embodiments thereof, which are provided by way of example and not by way of limitation.

Briefly, the above objects are provided by the use of hydroxy pivalyl hydroxy pivalate (HPHP) esters which contain stable neopentyl configurations in their chemical structure. These chemical structures exhibit low volatility and high thermal stability, the latter resulting in reduced fiber strength loss during high temperature processing and high temperature service conditions. HPHP is formed by reacting hydroxy pivalyl alcohol with hydroxy pivalic acid and is also referred to in the literature as neopentylglycol monohydroxypivalate. HPHP is commercially available from Eastman Chemical Products, Inc. A method of making HPHP is also set forth in U. S. Pat. No. 3,057,911.

Accordingly, the present invention comprises finishes for filaments of synthetic linear organic polymers which are hydroxy pivalyl hydroxy pivalate (HPHP) esters represented by the general formula:

cu, cu,

Cl-I H,

wherein, R and R are radicals alkanoic or alkenoic monocarboxylic acid having from 2 to 24 carbon atoms and preferably taken from the fatty acids. Both simple HPHP esters, i.e., those where R, and R are the same radical, and mixed HPHP esters are contemplated in the present invention. While it is preferred that the radicals R and R be derived from saturated and unsaturated straight chain acids, groups derived from branched chain acids such as the neo acids, for example neononanoic acid, etc., or iso acids such as isostearic acid, are contemplated. Typical specifications of some of the aforesaid products are summarized in Table l hereinbelow.

A high molecular weight glycol, HPHP, by virtue of stable neo configurations (at C and C in the above formula) in its chemical structure, exhibits high thermal stability and low volatility. This suggests that other neoglycol esters will also provide thermally stable fiber finishes.

The methods of preparation of the HPHP esters are known in the art of esterification. In general, two moles of acid or acid mixture is reacted, generally, with refluxing, with one mole I-IPHP in the presence of toluene or other suitable diluent. The uncatalyzed reaction occurs at temperatures ranging from C. to 265C. and over a period of time ranging from 4 to 12 hours until the theoretical amount of water of reaction is released and collected. The reaction may also be catalyzed with, for instance, an aromatic sulfonic acid, such as para toluene sulfonic acid, which will substantially reduce the reaction time. The resultant substantially completely esterified HPHP ester is then recovered, such as by stripping under vacuum, to obtain the ester product having a low free fatty acid value.

Some suitable illustrative esters coming within the scope of this invention are HPHP mono acetatemonooleate, HPHP dioleate, HPHP distearate, HPHP dilaurate, HPHP diheptanoate, HPHP di-caparate,

late, ethoxylated (8-15 mole) nonyl phenol, etc., which can be used singly or in combination as can. those setforth in the above example. Generally, the aqueous emulsion contains from 1 to 25% nonaqueous solids HP monolaurate, HPHP monopalmitate, HPHP which in turn consists of from 50 to 80 parts of the finn iso-nonanoace-monostearate. Mixed acids ish and 50 to 20 parts of the emulsifier. All percentages can be also employed to prepare HPHP esters. h rein are by weight.

TABLE 1 Suitable solvents for use in applying the finishes includes the lower molecular weight alkanols, such as TYPICAL SPECIFICATIONS OF HPHP ESTERS 10 ethanol or propanol, ketones such as acetone, and hy- Ffee E Saponification y y drocarbons such as toluene or petroleum ether. The HPHP Ester of And value value solvent selected should be compatible with the polymer Oleic Acid .03 235 9.5 to which it is pp gtelaric Acid .02 232 7.5 Other ingredients such as antistatic agents, emulsifi- P2123: 3 5;- 02 244 cation acids, lubricant acids to impart cohesion proper- Lauric 79% Acid .02 2 3 ties, etc. may be used in conjunction with the finishes Lauric Acid .01 292 4.0 f h .d d h d l Nonanoic Acid 01 347 10.0 0 t e present Invention provi e t ey 0 not serious y lso Nonanoic Acid .01 343 15.0 affect or alter the characteristics of said finishes. Heptanmc 336 The invention includes the application of the finishes to the filaments and the filaments which have been so The fimshes, y be apphefd dlrectly to filamenfs treated. The term filaments is to be understood as of the Synthetlc linear orgamc polymers or dlssolved m including monofilamentous and multifilamentous yarn a solvent or as an aqueous emulsion. In general, the whether twisted or not method of application is governed by the percentage of The synthetic linear organic polymers include poly lubncant y of f type of process amides such as polyhexamethylene sebacamide, polytype of equipment available. The mode of application kappa aminoundecanoic acid polyepsilon of the the m filaments depend upon h caprolactam, etc., acrylic polymers made largely from system which is most suited to the method of synthetic acrylomitrile, polyolefins Such as polymethylene, poly near proc?ssmg' Generally: from F 15 ethylene, polypropylene, etc., polyesters such as polypefcem fmlsh by welght of the organ: polyrfler ethylene terephthalate, and other polyesters formed by phed The fimsh may be further apPhed by reaction of a dihydric alcohol and a diacid, etc., and ternal addit on to the organic polymer prior to melt polyureas such as polyhexamethylene urea, etc spmnmg of Subsequent bleeding Surface The following examples further describe the inven- In preparing an aqueous emulsion containing the fintiom ish, any singular surfactant or combination of surfactants compatible with the finish capable of forming a EXAMPLE 1 Stable emulsion may be uuhzed' A sample aqueous Various HPHP esters formed according to the formueffwlsm prefpared usm'g cn vem1o nal Procedures lation previously set forth were tested for thermal stathe followmg proportlonal Ingredients: bility, resistance to smoke generation and discoloration EXAMPLE A 40 in comparison to commercial butyl stearate textile fiber finish. Both the esters of the present invention and the :60 parts HPHP esters control finish were subjected to strong oxidizing condil5 parts 10 parts glycerol monooleate (I 5 pans ethuxylated abom 25 mole cam" on tions, namely, each material was placed as a very thin 5 pans polyethylene glycol 400 dilaurale film in an aluminum dish which was exposed to high 35 Parts by temperature under atmospheric conditions.

The results in Table 2 clearly illustrate the high ther- Other suitable surfactants are sulfated glycerol triolema] stability, greater resistance to discoloration and ate, ethoxylated tridecyl alcohol and polyglycerol eslow amount of Smoke generation exhibited by the ters such as decaglycerol tetraoleate, triethanolamine HPHP esters as compared to the commercial butyl oleate, decaglycerol dilaurate, decaglycerol dicapry- Nate finish.

TABLE 2 HPHP di Stearate O leate Palmitate Laurate Heptanoate Butyl Stearate 20 min. at C.

Weight loss Nil Nil Nil Nil 0.6 1.3

Fuming None None None None None Light Discoloration None None None None None None 20 min. at 260C. Weight loss 0.5 0.75 0.7 1.0 13.0 25.5 Fuming None None None None Light Medium Discoloration None None None None None Light EXAMPLE n The fiber-to-fiber friction characteristics of 840/192 denier polyester yarn were tested by the solvent application of 1% HPHP ester by weight of the yarn in comparison to a control yarn from which the finish had been scoured. Conditions of test were a temperature of 70F. and a relative humidity of 25 percent. The attenuation was as follows:

Turn of Yarn l%(540) times Pendent Weight 20 gms.

Chart Speed 2.5 mm/sec.

Speed of Yarn 0.2 mm/sec.

Co-eff. of Mm. Between Friction Sli Sticks Control (scoured) 90 35 HPHP di oleate 65 50 HPHP di heptanoate 60 60 EXAMPLE III The fiber-to-metal friction characteristics of 840/ 192 denier polyester yarn which had been treated with a 1% solvent application of the HPHP ester, versus such characteristics of a scoured (without finish) yarn. Conditions of the test were as follows:

Temperature F 72 Relative Humidity percent 25 Speed of Yarn m/min. 100 Total Weight of Pulley grns. I Radians 5 The differential friction in grams, which is indicative of greater friction as it increases, is expressed in grams:

Finish Differential Friction None (Scoured Control) 190 HPHP di oleate llO HPHP heptanoate l The foregoing results indicate the superior fiber-tometal lubricity of HPHP esters.

EXAMPLE IV The smoke, fire and flash characteristics (A.O.C.S. Method Cc-9a-48) of the HPHP esters were compared to those of a commercial butyl stearate filament finish. The results which are as follows illustrates the minimized tendency of HPHP esters to cause smoke formation:

Smoke,F. Flash,F. Fire,F.

Butyl stearate 245 380 400 HPHP di ester of Stearic acid 375 590 625 Oleic Acid 410 585 640 Palmitic acid 375 555 605 EXAMPLE V Cords of 3 ply 1,300 denier polyester yarn treated with commercial finish (control) and with a selfemulsifiable composition of present invention were molded into test specimens using a rubber carcass stock.

The stock may be for example of natural, SBR or natural-SBR stock. After removal from the mold, adhesion can be determined by measuring the force required to separate the cord from the rubber. The measurement may be made at room temperature or at an elevated temperature and the force required for separation reported in pounds.

To determine U-adhesion, the treated cords were molded for 20 minutes at 290F. into the rubber in a suitable mold which produced U-shaped loops of cord embedded in 4 inch depth of rubber. These cord rubber assemblies were heated to 250F. in a special attachment for tensile tester and the force necessary to pull one end of the U out of the rubber was measured at a rate of separation of 30 cms/rninutes.

Cord fatigue life can be determined by the test described in ASTM Method D-885. In this test, the specimen is subjected to alternating compression and tension forces and the fatigue life is the number of cycles (commonly kilocycles) required to cause failure.

Strip Adhesion-Relative Peel Force U-Adhesion Fatigue Room Temp. Hi Temp. (lbs.) (Kilocycles) Commercial Finish (Control) I00 22 32 HPHP Di stearate NOTE: A higher number in each case indicates better performance.

EXAMPLE VI A tire cord treated with the finish of this invention (HPHP di stearate) and similar tire cord treated with commercial finish were maintained at 300F. for 48 hours in a sealed tube with oxygen (1 lb. pressure). Percentile breaking strength retention based on the original breaking strength prior to aging was expressed as thermal stability. A higher figure indicates the greater strength retention and less deterioration of the cord by finish at elevated temperature.

Breaking strength was measured according to ASTM Test Method D-2256.

Relative Thermal Stability Commercial HPHP Di stearate EXAMPLE vu Aqueous emulsion was prepared according to the formulation set forth in Example A. The HPHP esters of the following acids were used: acetic, propenoic, butyric, crotonic, valeric, caproic, caprylic, capric, lauric, myristic, palmitic, stearic, arachidic, behenic, lignoceric, lauroleic, myristoleic, palmitoleic, oleic, gadoleic, erucic, ricinoleic, linoleic, linolenic, eleostearic, licanic, arachidonic, and clupanodonic were used. Good properties as set forth above were noted.

EXAMPLE VIII Example VII was repeated using 99 parts by weight of water and 1 part by weight of the remaining materials. Good properties as set forth above were noted.

EXAMPLE IX Example VII was repeated using 75 parts by weight of water and 25 parts by weight of the remaining materials. Good properties as set forth above were noted.

EXAMPLE X Example VIII was repeated using 50 parts by weight of the finish (I-IPI-IP esters) and 50 parts by weight of the surface active emulsifier. Good properties as set forth above were noted.

EXAMPLE XI Example VIII was repeated using 80 parts by weight of the finish and 20 parts by weight of the surface active emulsifier. Good properties as set forth above were noted.

EXAMPLE XII Example IX was repeated using 50 parts by weight of the finish (I-IPl-IP esters) and 50 parts by weight of the surface active emulsifier. Good properties as set forth above were noted.

EXAMPLE XIII Example [X was repeated using 80 parts by weight of the finish and 20 parts by weight of the surface active emulsifier. Good properties as set forth above were noted.

The above discussion relates to filamentous materials as stated for use in a continuous operation wherein the filaments do not remain in a bath of the emulsion during treatment. In accordance with a second embodiment of the invention, it is desired to coat staple fibers of about one and one-half inches in length with the emulsion disclosed hereinabove by a non-continuous process wherein the staple fibers are placed in a vat or the like for an extended period of time and then removed. In this process, the amount of finish (diester) plus surfactent is from about 0.4 to about 2 percent by weight with the remainder water. Again, the ratio of finish to surfactant is from 50 to 80 percent by weight finish and 50 to 20 percent by weight surfactent.

Though the invention has been described with respect to specific preferred embodiments thereof, many variations and modifications will immediately become apparent to those skilled in the art. It is therefore the intention that the appended claims be interpreted as broadly as possible in view of the prior art to include all such variations and modifications.

What is claimed is:

1. An aqueous emulsion for application to synthetic linear organic polymer filaments in a continuous operation which consists essentially of:

a. a hydroxy pivalyl hydroxy pivalate diester represented by the formula:

CH: CH,

wherein R and R are taken from the class consisting of radicals of alkanoic and alkenoic monocarboxylic acids having from 2 to 24 carbon atoms,

b. A surface active emulsifier compatible with said diester, and

c. water, said emulsion containing from about 1 to about 25 percent nonaqueous solids, said nonaqueous solids containing from about 50 to about percent of said diester and from about 50 to about 20 percent of said surface active emulsifier, all of the above by weight.

2. An aqueous emulsion as set forth in claim 1, wherein said acids acids have/8 to 24 carbon atoms.

3. An aqueous emulsion according to claim 1, wherein said diester is taken from the class consisting of hydroxy pivalyl hydroxy pivalate distearate, hydroxy pivalyl hydroxy pivalate dioleate, hydroxy pivalyl hydroxy pivalate dipalmitate, hydroxy pivalyl hydroxy pivalate dilaurate, and hydroxy pivalyl hydroxy pivalate diheptanoate.

4. An aqueous emulsion according to claim 2, wherein said diester is taken from the class consisting of hydroxy pivalyl hydroxy pivalate distearate, hydroxy pivalyl hydroxy pivalate dioleate, hydroxy pivalyl hydroxy pivalate dipalmitate, hydroxy pivalyl hydroxy pivalate dilaurate and hydroxy pivalyl hydroxy pivalate diheptanoate.

5. An aqueous emulsion according to claim 1, wherein said surface active emulsifier is taken from the class consisting of glycerol monooleate, ethoxylated (about 25 moles) castor oil, polyethylene glycol 400 dilaurate, sulfated glycerol trioleate ethoxylated tridecyl alcohol, and the polyglycerol esters decaglycerol tetraoleate, triethanolamine oleate, decaglycerol dilaurate, decaglycerol dicaprylate and ethoxylated (8-11 moles) nonyl phenol.

6. An aqueous emulsion according to claim 2, wherein said surface active emulsifier is taken from the class consisting of glycerol monooleate, ethoxylated (about 25 moles) castor oil, polyethylene glycol 400 dilaurate, sulfated glycerol trioleate ethoxylated tridecyl alcohol, and the polyglycerol esters decaglycerol tetraoleate, triethanolamine oleate, decaglycerol dilaurate, decaglycerol dicaprylate and ethoxylated (8-11 moles) nonyl phenol.

7. Ar. aqueous emulsion according to claim 3, wherein said surface active emulsifier is taken from the class consisting of glycerol monooleate, ethoxylated (about 25 moles) castor oil, polyethylene glycol 400 dilaurate, sulfated glycerol trioleate ethoxylated tridecyl alcohol, and the polyglycerol esters decaglycerol tetraoleate, triethanolamine oleate, decaglycerol dilaumoles) nonyl phenol.

8. An aqueous emulsion according to claim 4, wherein said surface active emulsifier is taken from the class consisting of glycerol monooleate, ethoxylated (about 25 moles) castor oil, polyethylene glycol 400 dilaurate, sulfated glycerol trioleate ethoxylated tridecyl alcohol, and the polyglycerol esters decaglycerol tetraoleate, triethanolamine oleate, decaglycerol dilaurate, decaglycerol dicaprylate and ethoxylated (8-11- )moles) nonyl phenol.

9. An aqueous emulsion for application to staple fibers in a non-continuous which consists essentially of:

a. a hydroxy pivalyl hydroxy pivalate diester represented by the formula:

CH: CH,

H, CH,

wherein R and R are taken from the class consisting of radicals of alkanoic and alkenoic monocarboxylic acids having from 2 to 24 carbon atoms,

b. a surface active emulsifier compatible with said diester, and

c. water, said emulsion containing from about 0.4 to about 2 percent non-aqueous solids, said non-aqueous solids containing from about 50 to about 80 percent of said diester and from about 50 to about 20 percent of said surface active emulsifier, all of the above by weight.

10. An aqueous emulsion for application to staple fibers in a non-continuous precess as set forth in claim 9, wherein said acids have from 8 to 24 carbon atoms.

11. An aqueous emulsion according to claim 9, wherein said diester is taken from the class consisting of hydroxy pivalyl hydroxy pivalate distearate, hydroxy pivalyl hydroxy pivalate dioleate, hydroxy pivalyl hydroxy pivalate dipalmitate, hydroxy pivalyl hydroxy pivalate dilaurate, and hydroxy pivalyl hydroxy pivalate diheptanoate.

12. An aqueous emulsion according to claim 10, wherein said diester is taken from the class consisting of hydroxy pivalyl hydroxy pivalate distearate, hydroxy pivalyl hydroxy pivalate dioleate, hydroxy pivalyl hydroxy pivalate dipalmitate, hydroxy pivalyl hydroxy pivalate dilaurate, and hydroxy pivalyl hydroxy pivalate diheptanoate.

13. An aqueous emulsion according to claim 9, wherein said surface active emulsifier is taken from the class consisting of glycerol monooleate, ethoxylated (about 25 moles) castor oil, polyethylene glycol 400 dilaurate, sulfated glycerol trioleate ethoxylated tridecyl alcohol, and the polyglycerol esters decaglycerol tetraoleate, triethanolamine oleate, decaglycerol dilaurate, decaglycerol dicaprylate and ethoxylated (8-11 moles) nonyl phenol.

14. An aqueous emulsion according to claim 10, wherein said surface active emulsifier is taken from the class consisting of glycerol monooleate, ethoxylated (about 25 moles) castor oil, polyethylene glycol 400 dilaurate, sulfated glycerol trioleate ethoxylated tridecyl alcohol, and the polyglycerol esters decaglycerol tetraoleate, triethanolamine oleate, decaglycerol dilaurate, decaglycerol dicaprylate and ethoxylated (8-11 moles) nonyl phenol.

15. An aqueous emulsion according to claim 11, wherein said surface active emulsifier is taken the class consisting of glycerol monooleate, ethoxylated (about 25 moles) castor oil, polyethylene glycol 400 dilaurate, sulfated glycerol trioleate ethoxylated tridecyl alcohol, and the polyglycerol esters decaglycerol tetraoleate, triethanolamine oleate, decaglycerol dilaurate, decaglycerol dicaprylate and ethoxylated (8-11 moles) nonyl phenol.

16. An aqueous emulsion according to claim 12, wherein said surface active emulsifier is taken from the class consisting of glycerol monooleate, ethoxylated (about 25 moles) castor oil, polyethylene glycol 400 dilaurate, sulfated glycerol trioleate ethoxylated tridecyl alcohol, and the polyglycerol esters decaglycerol tetraoleate, triethanolamine oleate, decaglycerol dilaurate, decaglycerol dicaprylate and ethoxylated (8-11 moles) nonyl phenol.

17. A method of applying a finish to a synthetic linear organic polymer filament, which comprises the steps of a. providing a synthetic linear organic polymer filament, and

b. applying a finish to said filament which consists essentially of:

c. a hydroxy pivalyl hydroxy pivalate diester represented by the formula:

cu, cu,

CH3 CH3 wherein R and R are taken from the class consisting of radicals of alkanoic and alkenoic monocarboxylic acids having from 2 to 24 carbon atoms.

18. A method as set forth in claim 17 wherein said application in step (b) includes applying said finish to said fiber by internal addition to the organic polymer prior to melt spinning of said filament.

19. A method as set forth in claim 17, wherein said application in step (b) includes applying said finish directly to said filament.

20. A method as set forth in claim 17 wherein said application in step (b) comprises dissolving said finish in a solvent and then applying the resulting solution to said filaments.

21. A method as set forth in claim 17 wherein said application in step (b) comprises forming an aqueous emulsion of said finish and subsequently applying the aqueous emulsion to said filaments.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US3113369 *May 2, 1960Dec 10, 1963Monsanto ChemicalsYarn manufacture and products obtained thereby
US3428560 *Feb 27, 1967Feb 18, 1969Du PontYarn-lubricating composition
US3441953 *Oct 22, 1965Apr 29, 1969Herman T BuckleyEster of an aliphatic dihydroxy monocarboxylic acid and a textile material treated therewith
US3464922 *Dec 10, 1965Sep 2, 1969Drew Chem CorpTrimethylolalkane esters and method of treating textile filaments therewith
US3644143 *Aug 5, 1968Feb 22, 1972Ici LtdLubricating composition
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4452996 *Jan 27, 1983Jun 5, 1984Nippon Kayaku Kabushiki KaishaDi(meth)acrylate esters of hydroxypivalyl hydroxypivalate ε-caprolactone condensates
US5130196 *Oct 1, 1990Jul 14, 1992Chisso CorporationConjugate fibers and formed product using the same
Classifications
U.S. Classification252/8.84, 560/185, 428/394, 428/480
International ClassificationD06M13/192, D06M13/224, D06M13/00
Cooperative ClassificationD06M13/192, D06M13/224
European ClassificationD06M13/192, D06M13/224
Legal Events
DateCodeEventDescription
Mar 11, 1987AS02Assignment of assignor's interest
Owner name: PRO INTERNATIONAL INC., A NY. CORP.
Effective date: 19870227
Owner name: STEPPAN COMPANY, 22 WEST FRONTAGE ROAD, NORTHFIELD
Mar 11, 1987ASAssignment
Owner name: STEPPAN COMPANY, 22 WEST FRONTAGE ROAD, NORTHFIELD
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:PRO INTERNATIONAL INC., A NY. CORP.;REEL/FRAME:004685/0667
Effective date: 19870227
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:PRO INTERNATIONAL INC.;REEL/FRAME:004685/0667
Owner name: STEPAN COMPANY,ILLINOIS