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Patented 7, I ‘2,199,989 ‘UNITED’ STATES PATENT orrlca ' " 2.19am YARN CONDITIONING PROCESS AND‘ COMPOSITION THEREFOR Joseph B. Dickey and James G. McNally, Roch ester, N. Y., assignors to Eastman Kodak Com ' pany, Rochester, N; Y., a corporation of New ' Jersey No Drawing.‘ Application December 17, 1938,‘ I Serial No. 246,522 ‘ I . ‘7 Claims. (Cl. 28-1) _ This invention relates to the conditioning of to such yarns. A still further object is to" pro textile yarns and more particularly to the con vide yarn softening and lubricating formulas ditioning of ?laments and yarns composed of which can be readily removed vfrom the yarns organic derivatives of cellulose such asv cellulose by the usual scour baths. A still further object in acetate, cellulose propionate, cellulose acetate is to provide an improved method for the con propionate, and cellulose acetate butyrate, to ren ditioning of yarns, particularly those composed der them more amenable to textile operations of or containing organic derivatives of cellulose such as knitting and the like. a ‘such as cellulose acetate, whereby the yarn is , As is well known in the manufacture of yarns, rendered softand pliable and capable of employ 10 particularly those composed of or containing cel ment, in a variety of textile operations where lulose organic derivatives, it is necessary to treat _ complicated designs or stitches are employed. v the yarn in order to reduce the tendency toward Another object “is to provide an improved type breakage of the individual ?laments or "?bers of yarn which is especially amenable to textile when they are subjected to various mechanical operations including circular knitting, weaving, 15 strains and to lubricate the yarn in order to fa ‘spinning the manufacture of cut staple ?berand cilitate handling in such' operations as spinning, the like. Other objects will appear hereinafter. twisting, winding and reeling. It is also necessary These objects are accomplished by the follow - to treat'yarn to adapt it for use as warp or ?lling ing invention which, in its broader aspects, com or for themanufacture of various types of knitted prises the discovery that organic amine, mixed fabrics. In knitting, it is particularly important organic amine and metallic salts of organic acids 20 that the yarn be soft and pliable in order that having the general formula: ' it may conform readily tothe contour of the. needles and thus produce a closely knit fabric free from such defects as “stitch distortion,” “pin holes,” “laddering,” and the like. ' Heretofore it has been proposed to employ softening agents such as polyhydric alcohols and similar agents as ingredients of yarn condition ing or lubricating formulas, generally in connec tion with mineral, animal or vegetable oils. It ,Where X is a metal, ammonia or derivative and 30 has been found, however, that most of the known Y is the same as X and in some cases may be softening agents and the various formulas con omitted, may be used as yarn conditioning agents taining them have certain drawbacks, one of the and particularly as softening agents, with or with most serious of which is high vapor pressure, and out the addition of animal, mineral, or vegetable 36 in some cases too drastic a solvent action on the oils, in the treatment of yarns composed of or yarn. Many of such agents possess slight or in containing organic derivatives of cellulose. We sufficient solvent power for the lubricants with have found that these compounds when employed which they are used, and it is accordingly nec as described in the'detailed examples set forth essary to employ blending agents or emulsifying " below have a slight solvent and/or softening ac 40 agents in order to obtain operable yarn treating tion on cellulose organic ‘derivative yarns ‘which ‘ formulas. In addition, many of the known sof renders'such yarns soft and pliable without ‘at tening and lubricating agents are insufficiently the same‘ time having too drastic an ‘action , soluble in water to permit satisfactory removal ‘ thereon. - by aqueous scour baths. , , In order to prepare the salts we‘ may use any '48 This invention has as its principal object to pro suitable organic base or any inorganic hydroxide. 45 . vide an entirely new class of yarn conditioning In accordance with the invention these com agents which are particularly adapted for the pounds may be applied directly to the yarn during treatment of yarns composed of or'containlng or after spinning, or may be added to the spinning organic derivatives of cellulose and capable of solution itself. -We have found that these com 50 lubricating, softening, deelectrifying and other‘ pounds have exceptional solvent powers which wise rendering such yarns more amenable to knit enable them to dissolvemineral oils and accord ting and other textile operations. A further and ingly they may be, and preferably are, employed speci?c object is to provide a class -of condition as ingredients of yarn conditioning or lubricating ing agents whichaugment or assist the lubri formulas in conjunction with agents which func cating action of various lubricants 'when applied ction wholly or partially as lubricants. 2 . 2,199,999 We have also found that the above mentioned Example 5 compounds are particularly valuable .as anti-static agents when applied to ?laments, threads, fab CgHn—-N'H—HO—g—GHr-O-CH:—8—NHQ / rics, etc., composed of or containing organic de ....5_ rivatives of cellulose, such as cellulose acetate, cellulose propionate, cellulose acetate butyrate, _i_ _________________________ __ 5 ‘ and the like, and to textile materials in general. In the following examples and description, we have set forth several of the preferred embodi ;s_ 10 ments of our invention, but they are included _Neat's-loot oil.. 7 o o ' 05 10 merely for purposes of illustration and not as a Example 6 ' limitation thereof. HC—-CH ‘ : HC-CH Example 1 up: i”: o_=s=o n 15 Diglycolic dioleyl amine salt is applied to tex- - tile materials (silk, cotton, wool, viscose, cellulose acetate, etc.) by means of a .wick, bath, roller, _3_ spray, etc., to facilitate their knitting, weaving, -3 20 spinning and the like. Yarns lubricated with the above types of lubricants are of special value in 20 the preparation of cut staple ?bers. These ?bers Blown neat's-ioot oil ............... ..‘ ...................... ._ 99-90 may be oiled before or after cutting. Example 7 Example 2 __s._ A conditioning liquid is made up as follows: OHz-O—C;Hl—-0-8-OHr8—OH.HO—N—-(CH;); 1-10 25 Parts B,B'-Tetrahydrofurfuryloxy ethyl ether ____ __ 90 --B-— CHaO Water- a ' 5 30 Diglycolic or thiogylcolic acid ditetrahydro O==S=O furfurylamine salt _______________ __Y._____ 5 Blown olive oil. I _. 99-90 60 and applied to textile materials such as silk, wool, Example 8 cellulose acetate, etc., as described in Example 1. If the yarn is intended primarily for knitting, CaHr-OCgHr-OCIHrf-O8—CH:—O——CH:—g-ONH4 ' the amount of conditioning liquid applied may vary from 4-25% by weight of the yarn and if for :5: .................. -- 1-10 '35 weaving, between 1-5% by weight. ' Cellulose acetate ?laments treated as described above are quite soft and pliable and give im I 0=s=o proved results in various textile operations such Blown sperm oil ............................................ .. A0 as weaving, knitting, etc., and especially in the Example 9 production of cut staple yarn. , Other examples of yarn conditioning composi tions which may be applied to various types of cinhnm-no-g-cH=—0—cH,-8-oH.NH,—c4H. yarns, particularly those composed of or con -ésl- .............. .- 1-10 :45 taining cellulose acetate, cellulose acetate pro pionate, cellulose acetate butyrate, and similar cellulose organic acid esters in accordance with 3mm oil 0:8:0 ...... __ 99-90 our invention and which render such yarns soft 60 and pliable and especially well adapted for vari Example 10 $50 ous textile operations, particularly knitting, are Di-?-methoxy ethyluocinate.s .............................. _. 26 as follows: 0:114 *5‘ Example 3 ' 0/ \mno-c-cm-o-cm-o-ox __________ _- 1-10 55 i’arts \clHc/ o ~5- o v ' HtN—Og-OHl-0—CHr-8—OK ........ _- 2 {55 o=s=o , __s_ < '1‘ oil ..... .. 14-65 _ Example 11 ’ 00 0/v :8: \O Blown teaseed oil ........................................... _- 99-90 . Blown olive oil.-. 40 1CqHyN-HO-C-CHrO-CHr8-OH—C¢H||N(C|H‘OH)| Glycerol ‘ pronirmafn 58 on. CH; -s- ........................ _- l-l0 65 Example 4 - ~ -s. o .65 (02KB)lNH—H0—8—CH:—0-;OHl—8—0H-—NHPCH8 O=S=0 -s- _____ Q. ____________________ _- 5 Example 12 ._g‘.... 70 lolig‘ign?no-c-oH=-o+oH,-o—o11.bié§iamme..-- “tit ~70 o _ _s_ o v v _5<\ 0 I 0 Water 5 Olive oil 60 76 To furiuryl lactate .................................... -- 30 0=S==O' ‘ 1 2,199,989 . Example 13 ous ingredients, these percentages may vary - widely depending upon the particular purpose for |Water_.._ __ ~ " 70 Water soluble cellulose ester _____ ___,,. _________ __ 16 which the composition is intended. For example, Cetylamine.H0--vg——CHg—-0-—CH,-—g-—0H if it is desired to control the solvent or softening action of the conditioning agent, the amount of / the agent may be adjusted as, for example, by , ji- ----------------- -- 5 reducing the amount of- the agent and corre spondingly increasing the amount of oil or other >o==s-o ingredient. _ 10 Sulfonated castor oil _________________________ __ 10 While we have described our invention with 10 particular reference to the treatment of yarns _ Any of the above compositions may be applied composed of organic derivatives of cellulose such to the yarn intended for use in circular knitting as cellulose acetate, the conditioning agents and by means of a bath, wick, spray, roller, pad or formulas described herein are applicable to the ll any suitable means.