US2196755A - Yarn conditioning process - Google Patents

Description

Patented Apr. 9, 1940 UNITED STATES 2,196,755 YARN CONDITIONING PROCESS Joseph B. Dickey, Rochester, N. Y., assignor to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application December 21, 1938, Serial No. 247,098

14 Claims.

This invention relates to the conditioning of textile yarns and more particularly to the conditioning of filaments and yarns composed of organic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose acetate propionate, and cellulose acetate butyrate, to

- render them more amenable to textile operations such as knitting and the like.

As is well known in the manufacture of yarns, particularly those composed of or containing cellulose organic derivatives, it is necessary to treat the yarn in order to reduce the tendency toward breakage of the individual filaments or fibers when they are subjected to various mechanical strains and to lubricate the yarn in order to facilitate handling in such operations as spinning, twisting, winding and reeling. necessary to treat yarn to adapt it for use as warp or filling or for the manufacture of various types of knitted fabrics. In knitting, it is particularly important that the yarn be soft'and pliable in order that it may conform readily to the 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 conditioning or lubricating formulas, generally inconnection with mineral, animal or vegetable oils. It has been found, however, that most of the known softening agents and the various formulas.

containing them have certain drawbacks, one of the most serious of which is high vapor pressure, and in some cases too drastic a solvent action on the yarn. Many of such agents possess slight or insufiicient solvent power for the lubricants with which they are used, and it is accordingly necessary to employ blending agents or emulsifying agents in order to obtain operable yarn treating formulas. In addition, many of the known softening and lubricating agents are insufiiciently soluble in water to permit satisfactory removal by aqueous scour baths.

This invention has as its principal object to provide an entirely new class of yarn conditioning agents which are particularly adapted for the treatment of yarns composed of or containing organic derivatives of cellulose and capable of lubricating, softening and rendering such yarns more amenable to kniting and other textile operations. A further and specific object is to provide a class of conditioning agents which augment or assist the lubricating action of various 55 lubricants when applied to such yarns. A still It is also capable of employment in a variety of textile operations where complicated designs or stitches are employed. Another object is to provide an improved type of yarn which is especially amenable to textile operation including circular knitting, weaving, spinning and the like. Other objects will appear hereinafter.

These objects are accomplished by the following invention which, in its broader aspects, comprises the discovery that phosphated polyhydroxy alkoxyalkyl ethers and alkyl and aryl ethers of monoand poly-functional alcohols having the following general formula:

z)t1n'CII C z--[ H2)il where Y is aphosphoric acid ester derivative, said ester being derived from the group of compounds consisting of the free acid, its esters, and organic and inorganic salts, R isan alkyl group, R R and R are organic radicals selected from the group consisting of the substituted and unsubstituted alkyl, aryl or heterocyclic groups, L is a mono-valent substituent selected from the group consisting of hydrogen, hydroxy, acetal, ether, etc., and n is 0, 1, 2, etc., and b is 0, l, 2, etc., may be used as yarn conditioning agents and particularly as softening agents, with or without the addition of animal, mineral, or vegetable oils in the treatment of yarns composed of or containing organic derivatives of cellulose. I have found that these compounds when employed as described in the detailed examples set forth below have a\slight solvent and/or softening action on cellulose organic derivative yarns which renders such yarns soft and pliable without at the same "time having too drastic an action thereon.

Examples ofthe preparation of typical compounds of this typeare as follows:

- PREPARATION OF COMPOUNDS Example 1 28.6 gm. of p-hydroxyethyl cetyl ether are dissolved in chloroform and treated with 16 gm. of phosphorus oxychloride in the cold and the reaction is completed by warming. The chloride is hydrolyzed with aqueous sodium bicarbonate and the compound obtained by concentrating the liquors. The disodium p-hydroxyethyl cetyl ether phosphate is water soluble. The product of reaction has the formula:

Example 2 One mole of CHz-O OieHu HOH CHPGHOH-CHaOH is reacted in a mixture of dioxane and pyridine with one mole of (C16H33O)2POC1.

Example 3 One mole of OHa-O CuHn HOE ocm-cHoH-om-o our! is reacted as previously described with two moles of phosphorus oxychloride and the potassium salt prepared.

Example 4 One equivalent of oleyl (OC2H4)n-OH is treated in a chloroform pyridine mixture with one equivalent of and the product worked up as described in Example 1 so as to obtain a mono-potassium salt.

The reaction product has the formula:

25.2 gm. of HO-C2H4OC1oH2o -OC2H4OH are heated with gm. of phosphoric acid at 110-140 under reduced pressure for twenty hours. The phosphate thus obtained may be treated, if desired, with bases such as sodium, potassium or ammonium hydroxide; tetramethylammonium hydroxide, etc., triethylamine, triethanolamine, dimethylcyclohexylamine, morpholine, ditetrahydrofurfurylamine, etc. to prepare mono or dibasic salts. The reaction product has the formula:

no-mm-Omm-omm-o P-OZ Example 6 31.4 gm. of glyceryl mono-cetyl ether are dissolved in pyridine and treated with one equivalent of CmHa'P- fi i and the reaction is completed by warming. The

pyridine is removed under reduced pressure and the chloride is hydrolyzed. Any desired basic salt may be prepared. If desired, two phosphate groups may be introduced. The reaction product has the formula:

GET-(Khu na CHOH CHz-O P-O 015 31 Example 7 32.5 gm. of

(LE-0011K I CHiOH are treated in chloroform with 50 gm. of

012 Cl2|P-N and the reaction is carried out and worked up as previously described. The tetramethyl ammonium hydroxide or benzyl trimethyl ammonium hydroxide salt is prepared. The reaction product has the formula:

is dissolved in pyridine and treated with one or more equivalents of and the product worked up to give an ethanolamine salt.

Example 10 28.8 gm. of

CH2CH2 era-00112 011 OH:

H-OCeHn 0 HIOH Example 18 A conditioning llq'uid particularly useful in the preparation of cut staple fibers made of cellulose acetate and which maybe used for other textile operations is made up as follows:

- Parts Water soluble cellulose ether l CHr-O- P-ONa ONe Hr-O Naphthenyl 1-10 Olive oil 98-89 Other examples of yarn conditioning compositions which may be applied to various types or yarns, particularly those composed of or containing cellulose acetate, cellulose acetate propionate,

cellulose acetate butyrate, and similar cellulose organic acid esters in accordance with my invention and which render such yarns soft and pliable and especially well adapted for various textile operations, particularly knitting, are as follows:

Example 19 I Parts Blown olive oil.-." 69-80 Oleyl (O CIH4)1, r, ete., P-ONa s OCH: 1-10 Tetrahydroiurluryl lactate Example 20 OH Cyclohexylamine salt 2-5 H0 0113.0 omHn-0-0,H. 0-P

O OH Cyelohexylamine salt N cat's-foot oil 98-95 Example 21 CHr-O-CHQ O HOH H-O-Naphthenyl /0Na Iii-01" 0 Blown neats-loot oil 79-50 Ethanolarnine propionate butyrate 20-30 Example 2 2 (H Tetramethylammonium hydroxide salt CHz-O P LB: O H Tetramethylammonium hydroxide salt... l-lO 6 Sperm oil Q 9990 Eaiample 23 Parts Pentaerythritol triethyl ether diammonium phosphate. l-

Blown sperm oil $140 Sodium sulfate 2 S OH 'lriethanolaniine. l-lQ (n is l, 2, etc.)

Example 28 Fibers; threads, filaments, etc. composed of any textile material/in general or cellulose acetate in particular can be lubricated for various textile operations such as weaving, preparation of staple yarns, thereto by means of a bath, suitable compound chosen from the group of compounds claims in this application, as for example: e

etc. by applying CnGar-O 01114-0 IklOH-NCHLOHM]: and

CHr-OOiaHu CH-OCnfiu HsO-P-OK I 0051111 Any of the above composition may be applied to the yarn intended for use in circular knitting by means of a bath, wick, spray, roller, pad or any suitable means. The amount of conditioning liquid applied may vary between 5-25% by weight of the yarn. Usually, however, the amount of conditioning liquid applied is about 10-15% by weight ofthe yarn. Yarn composed of cellulose acetate conditioned as described above gives excellent results when used in the etc. 0

circular knitting process.

As will be apparent from the above-examples and description the conditioning agents of 'my invention maybe applied by a. wide variety of methods. For example, I may employ the agent as an ingredient of the spinning dope from which the filaments are formed, the amount of the agent so employed depending upon a number of factors, tive' used in making the yarn, the solvent or solvent combination used in making up the spinning solution, and the degree of softness or pliability desired in the yarn, etc.

3 If the conditioning agent is to be applied to the 3 yarn after spinning, this maybe done by bringing the yarn in contact with a wick, roll, or felt wet therewith, or the liquid may be applied by im-' merslon, spray, or otherwise. The particular point at which the liquid is applied may vary.

'It may, for example, be applied to the yarn inknitting, spinning,

wick, spray, etc. a

such as the particular cellulose derivaare dissolved in a mixture of chloroform and pyridine and treated with 16 gm. of

OCH: II/ 01.?

N(CH:):

and the reaction is completed by warming. The reaction product has the formula:

CHQ.CHQ CHr-OCHr-(EH CH2 (gH-OCs'Hn O dm-or-oom 0 Mom Example 11 One equivalent of O-o-cmKooum-on is treated with one equivalent of phosphorus pentasulfide in an oil bath at 50-150 until the reaction is complete. The product is treated with water and neutralized with morpholine. The reaction product has the formula:

C ll,

Example 12 One equivalent of the reaction product from tetrahydrofurfuryl alcohol and ethylene oxide is treated in boiling chloroform with phosphorus pentoxide. The reaction product is treated with 33.4 gm. of m-hydroxy cetyl phenyl ether are dissolved in a mixture of chloroform and pyridine and treated with 16 gm. of phosphorus oxychloride. The reaction product is worked up as previously described and any desired salt such as the triethylamine, benzltrimethylammonium hydroxide, etc. prepared. The reaction produce has the formula:

In a similar manner we may react:

is dissolved in a mixture of dioxan and pyridine and reacted with one mole of POC13. The trimethylbenzylammonium hydroxide salt is prepared.

Example 15 2 pounds of 1-methylamine-4-ethy1aminoanwith one pound of and poured into 200 gallons of water, then heated to 60-85. 100 pounds of cellulose acetate in the form of taffeta, crepe fabrics, etc. are entered and dyed a deep blue shade. Softwater is not necessary with a dispersing agent of this type.

In accordance with the invention these compounds may be applied directly to the yarn during or after spinning. or may be added to the spinning solution itself. I have found that these compounds have exceptional solvent powers which enable them to dissolve mineral oils and blown and unblown, drying and semi-drying, vegetable and animal oils and accordingly they may be, and preferably are, employed as ingredients of yarn conditioning or lubricating formulas in conjunction with agents which function wholly or partially as lubricants.

In the following examples and description I have set forth several of the preferred embodiments of my invention, but they are included merely for purposes of illustration and not as a limitation thereof.

My invention will be more readily understood by reference to the following examples in which typical applications of the invention are set forth.

Example 16 UIIOH Dimethylcyclohexylamine salt is applied to textile materials (silk, wool, cotton, viscose, cellulose acetate,'etc.) by means of a bath, wick, spray, roller, etc., to facilitate their knitting, weaving, spinning etc. Yarns lubricated with the above type of lubricant are of special value in the preparation of cut staple fibers. These fibers may be oiled before or after cutting.

Example 17 A conditioning liquid is made up as follows:

Parts by weight l\ 4) 0H Diethyl cyclo hexylamine salt Wafer and applied to textile materials such as silk, wool, viscose, cotton, cellulose acetate, etc., as in Example 16. .If the yarn is intended primarily for knitting the amount of conditioning liquid applied may vary from 4-25% by weight of the yarn and if for weaving between 1-5% by weight. Cellulose acetate filaments treated as described are quite soft and pliable and give improved results in various textile operations such as weaving, knitting etc., and especially in the preparation of cut staple fibers.

Other examples of suitable lubricating mixtures having anti-static properties which are used as described in Examples 16 and 17 follow.

ple fiber manufacture, the liquid may be applied to the yarn prior to, or after cutting into staple lengths.

The amount of the agent so employed will vary widely depending upon the results desired, the specific nature of the material to which the agent is applied, the use to which the yarn is eventually to be put and other factors. For example, in a given case where a cellulose organic acid ester yarn such as a yarn composed of cellulose acetate, is intended for knitting, about 4 to 25% or more by weight, based on the weight of the dry yarn, may be satisfactory, while if the yarn is intended for weaving, the amount may vary between about 1 and 5%.

Although in the above examples I have referred primarily to yarn treating compositions containing only the conditioning agent and an oil, other ingredients such as solvents, nonsolvents, emulsifying agents, blending agents and the like, may be added within the scope of my invention. Likewise, various dyes or other coloring matter may be included in case it is desired to permanently or fu'gitively tint or dye the ma-v terial undergoing treatment.

Although I have found it convenient to illustrate my invention by reference to compositions containing specific percentages of the various ingredients, these percentages may vary widely depending upon the particular purpose for which .the composition is intended. For example, 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 reducing the amount of the agent and correspondingly increasing the amount of oil or other inredient.

While I have described my invention with particular reference to the treatment of yarns composed of organic derivatives of cellulose such as cellulose acetate, the conditioning agents and formulas described herein are applicable to the tor, neats-foot, sperm and other oils.

conditioning of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials.

The term yarn as used herein and in the claims is to be understood as including a single filament, a plurality of filaments associated into the form of a thread, either of high or low twist, single or multiple threads associated or twisted together, composite threads composed of a mixture of natural and artificial filaments or a composite thread formed by twisting together individual strands of natural or artificial materials, as well as cut staple fibers produced from natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.

As indicated above; the yarn conditioning agents of my invention are exceptionally good solvents for a wide variety of mineral, blown and unblown, drying and semi-drying animal and vegetable oils such as cottonseed, olive, cas- This enables them to be used with any of such oils in making up a variety of yarn treating formulas of varying composition.

The yarn conditioning method and compositions of my invention possess many outstanding advantages. The fundamental and outstanding characteristic of the agents employed in accord ance with the invention is their ability to soften yarns, especially those composed of or containing organic derivatives of cellulose such as cellulose acetate and render them soft and pliable and amenable to various textile operations, especially operations such as those involved in weaving and knitting where complicated designs or stitches are employed, without too drastic an action on the yarn material. Another outstanding characteristic of these compounds is their exceptional solvent power for a Wide variety of mineral, animal, and vegetable oils and their ability to act as lubricating assistants in conjunction with these oils when applied to such yarns. In addition, due to their solubility in water, they may be readily removed from yarns and fabrics bymeans of the usual aqueous scour baths. By employing the yarn conditioning agents and method of my invention as herein described, one is enabled to obtain highly satisfactory results in the manufacture of yarns and woven fabrics and especially the production from these yarns of closely knit fabrics free from defects such as pin holes, stitch distortion, laddering and the like.

What I claim is:

1. The process of conditioning yarn to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an ether selected from the group consisting of the phosf phated polyhydroxy alkoxyalkyl ethers, and alkyl and aryl ethers of monoand poly-functional alcohols.

2. The process of conditioning yarn composed of or containing organic derivatives of cellulose to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an ether selected from the group consisting of the phosphated polyhydroxy alkoxyalkyl ethers, and alkyl and aryl ethers of monoand polyfunctional alcohols.

3. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which,

comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an ether selected from the group consisting of the phosphated polyhydroxy alkoxyalkyl ethers, and alkyl and aryl ethers of monoand poly-functional alcohols.

4. The process of conditioning yarn composed. of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an ether selected from the group consisting of the phosphated poly-hydroxy alkoxyalkyl ethers, and alkyl and aryl ethers of monoand poly-functional alcohols, and a textile lubricant.

5. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component glycerol dioleyl ether-phosphate diethyl cyclohexylamine salt.

6. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component disodium thio-phosphate of ethylene glycol naphthenyl ether.

'7. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, Weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component pentaerythritol triethyl ether phosphate diammonium salt.

8. A conditioning agent for rendering textile yarns composed of or containing organic derivatives of cellulose more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises an ether selected from the group consisting of the phosphated polyhydroxy alkoxyalkyl ethers, and alkyl and aryl ethers of monoand poly-functional alcohols, and a textile lubricant.

9. Textile yarns amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant containing as 40 its essential lubricating and softening component an ether selected from the group consisting of the phosphated polyhydroxy alkoxyalkyl ethers, and aIkyIKand aryl ethers of monoand polyfunctional alcohols.

10.,TeXtile yarns composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning, and the like impregnated with a conditioning agent comprising an ether selected from the group consisting of the phosphated polyhydroxy alkoxyalkyl ethers, andalkyl and aryl ethers of monoand poly-functional alcohols.

11. Textile yarns composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a conditioning agent comprising an ether selected from the group consisting of the phosphated polyhydroxy alkoxyalkyl ethers, and alkyl and aryl ethers of monoand. poly-functional alcohols, and a textile lubricant.

12. Textile yarns composed of or containing cellulose acetate amenable totextile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising glycerol dioleyl ether-phosphate diethyl cyclohexylamine salt.

13. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising disodium thio-phosphate of ethylene glycol naphthenyl ether.

14. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting,'weaving, spinning, and the like, impregnated with a lubricant comprising pentaerythritol triethyl ether phosphate diammonium' salt.

JOSEPH B. DICKEY.