Patented 7, I ‘2,199,989

‘UNITED’ STATES PATENT orrlca ' " 2.19am 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 . A still further object is to" pro 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 (, , , 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. The amount of condition conditioning of many other types of cellulose ing liquid appliedv may vary between 5-'25% by derivative yarns such as those composed of or weight of the yarn. Usually, however,- the containing cellulose‘ propionate, cellulose bu amount of conditioning liquid applied is about tyrate, cellulose acetate propionate,. cellulose 10-15% by weight of the yarn. Yarn composed, acetate butyrate, ethyl cellulose, methyl cellulose, of cellulose acetate conditioned as described benzyl cellulose and others, as well as to the above gives excellent results when used in the conditioning of silk, wool, cotton, viscose and circular knitting process. other natural or arti?cial materials. As will be apparent from the above examples The term “yarn" as used herein and in the and description the conditioning agents of our claims is to be understood as including a single invention may be applied by a wide variety of ?lament, a plurality of filaments associated into methods. For example, we may employ the the form of a thread, either ‘ of high or agent as an ingredient of the spinning dope from low twist, single or multiple threads associated which the ?laments are formed, the amount of or twisted together, composite threads composed the agent so employed depending upon a number of a mixture of natural and arti?cial ?laments of factors, such as the particular cellulose deriva or a composite thread formed by twisting together tive used in making the yarn, the solvent or sol individual strands of natural or arti?cial ma vent combination used in making up the spinning terials, as well as cut staple fibers’ produced from solution, and the degree of softness or pliability natural and/or arti?cial ?laments or threads and desired in the yarn, etc. . spun yarn produced from such staple ?bers. If the conditioning agent is to be applied to the 35 As indicated above, the yarn conditioning 35 vyarn after spinning, this may be done by bring agents of our invention are exceptionally good ing the yarn in contact with a wick, roll, or felt solvents for a wide variety of mineral, blown and wet therewith, or the liquid may be applied ,by unblown, drying and semi-drying animal and immersion, spray, or otherwise. The particular vegetable oils such as cottonseed, olive, caster, point at which the liquid is applied may vary. neatsfoot, sperm and other oils. This enables It may, for example, be applied to the yarn inside them to be used with any of such oils in making -or outside the spinning cabinet, between the guide up a variety of yarn treating formulas of varying and godet roll, between the godet or other roll composition. ‘ or guide and the point of winding and/or twisting. The yarn conditioning method and composi In some cases, the liquid may even be applied to tions of our invention possess many outstanding the yarn after winding onto cones, spools, bobbins, advantages. The fundamental and outstanding or the like or by the so-called “bobbin to bobbin” characteristicof the agents employed in accord method. In the case of staple ?ber manufacture, ance with the invention is their ability'to soften the liquid may be applied to the yarn prior to, yarns, especially those composed of or containing or after cutting into staple lengths. ' organic derivatives of cellulose such as cellulose 50 The amount of the agent so employed will vary acetate and render them soft and pliable and widely depending upon the results desired, the amenable to various textile operations, especially - speci?c nature of the material to which the agent operations such as those involved in the manu is applied, the use to which the yarn is eventually facture of cut staple ?bers and in weaving and to be put and other factors. For example, in a knitting where complicated designs or stitches are 55 given case where a cellulose organic acid ester employed, without too drastic an action on the » yarn such as a yarn composed of cellulose acetate, yarn material. Another outstanding character is intended for knitting, about 4 to 25% or more istic of these compounds is their exceptional sol by weight, based on the weight of the dry yarn, vent 'power for a wide variety of mineral, animal, may be satisfactory, while if the yarn is intended and vegetable oils and their ability to act as 60 for weaving, the amount may vary between about lubricating assistants in conjunction with these 1 and 5%. . - ’ oils when applied to such yarns. In addition, due Although in the above examples we have re to their solubility in water, they may be readily ferred primarily'to yarn treating compositions removed from yarns and fabrics by means of the containing only the conditioning agent and an oil, usual aqueous scour baths. By employing the 65. other ingredients such as solvents, non-solvents, yarn conditioning agents and method of our in emulsifying agents, blending agents and the like, vention as herein described, one is enabled to may be- added within the scope of our invention obtain highly satisfactory results in the manu Likewise, various dyes or other coloring matter facture of yarns and woven fabrics and especially 70 may be’included in case it is desired to per the production from these yarns of closely knit 70 manently or fugitively tint or dye the material fabrics free from defects such as pin holes, stitch undergoing treatment. distortion, laddering and the like. Although we have found it convenient to il What we claim is: ‘ lustrate our invention by reference to composi 1. The process of conditioning yarn to render Tl tions containing speci?c percentages of the vari ‘it more amenable to textile operations including 4V ‘2,199,989 knitting, weaving, spinning, the manufacture of amine and metallic salts of organic acids having staple ?bers, and the like, which comprises ap ' the general formula: plying a lubricating and anti-static composition containing as its essential lubricating and anti static component a salt selected from the group consisting of organic amine, mixed organic amine wherein X and Y are substituents selected from _ and metallic salts of organic acids having the the group consisting of metals and organic bases general formula: and Z is a substituent selected from the group consisting of 0. o 10 X.HO—g-—OH:—Z'—CH|-—g—-OH.Y o 0\ /o 10 v-—-O——, —B-—, —L_—, and :5: ,Y wherein X and Y are substituents selected from the group consisting of metals and organic bases 5. Textile ‘yarns amenable to textile opera and Z is a substituent selected from the group tions including knitting, weaving, spinning, the consisting of ‘ _ manufacture of staple ?bers, and the like impreg- - ’ nated with a lubricant and anti-static composi v15 e _ o o\ /o -o—, “5-, -g_-, and DB1 tion containing as its essential lubricating and anti-static component a salt selected from the 2. The process of conditioning yarn composed’ group consisting of organic amine, mixed organic of or containing organic derivatives of cellulose amine and metallic salts of organic acids having to render it more amenable to textile operations the general formula: 20 I including knitting, weaving, spinning, the manu facture ‘of staple ?bers, and the like which com prises applying a lubricating and anti-static com position containing as its essential lubricating and wherein X and Y are substituents selected from anti-static component a salt selected from the the group consisting of metals and organic bases group consisting of organic amine, mixed organic and Z is a substituent selected from the group amine and metallic salts of organic acids having _ consisting of the general formula:

- 0 X.HO—-g—.QHQ—Yr-CH2-g-OH.Y 6. Textile yarns composed of or containing or wherein X and Y are substituents selected from ganic derivatives of cellulose amenable to textile the group consisting of metals and organic bases operations including knitting, weaving, spinning, and Z is a substituent selected from the group the manufacture of staple ?bers, and the like consisting of impregnated with a conditioning agent compris .' Q \ /O ing a salt selected from the group consisting of —0—, —S—-, —g—-, and 2S: organic amine, mixed organic amine and metal lic salts of organic acids having the general for 3. The process of conditioning yarn composed mula: ' . of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, the manufacture of staple ?bers and the like which comprises ap wherein X and Y are substituents selected from ' plying a lubricating and anti-static composition the group consisting of metals and organic bases containing as its essential lubricating and anti and Z is a substituent selected from the group ' static component a salt selected from the group consisting of . . consisting of organic amine, mixed organic amine 0 ' o\ / and metallic salts of organic acids having the —O-,—SQ'—,-—g—,snd>S: , general formula: ' '7. Textile yarns composed of or containing or ganic derivatives of cellulose amenable to tex- , tile operations including knitting, weaving, spin ning, the manufacture of staple ?bers, and the wherein X and Y are substituents selected from like impregnated with a conditioning agent com the group consisting of metals and organic bases prising a salt selected from the group consisting 55 and Z is a substituent selected from the group of organic amine, mixed organic amine and consisting of _ - metallic salts of organic-acids having the general‘ ' 0 o\ / formula: -o-, -s—, -g-, and lei 0 0 . 4. The process of conditioning yarn composed , x.Ho-1J:-oHr--z-oH=—g—oH.Y 60 of or containing cellulose acetate to render it wherein X and Y are substituents selected from 60 more amenable toltextile operations including the group consisting of metals and organic bases knitting, weaving, spinning, the manufacture of and Z is a substituent selected from the group staple ?bers, and the like, which comprises ap consisting of . ' g plying a lubricating and anti-static composition (I) 0\ /o 65 containing as its essential lubricating and anti -o-, -f‘-s¢-, -t-, and is: . 65 static component a salt selected from the group JOSEPH 'B. DICKEY. consisting of organic amine, mixed organic JAMES G. McNALLY.