US2196753A

US2196753A - Yarn conditioning process

Info

Publication number: US2196753A
Application number: US246515A
Authority: US
Inventors: Joseph B Dickey; James G Mcnally
Original assignee: Eastman Kodak Co
Current assignee: Eastman Kodak Co
Priority date: 1938-12-17
Filing date: 1938-12-17
Publication date: 1940-04-09
Anticipated expiration: 1957-04-09

Description

.atente Apr. Q 1946 YARN QONDITIONIN G PRGCESS Joseph B. Dickey and James G. MeNally, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application December 17, 1938, Serial No. 246,515

'7 Claims.

This invention relates to the conditioning of textile yarns and more particularly to the condi- V tioning 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. It is also 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 fab-- ric 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 in connection 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 insufl'iciently 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 knitting 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 lubricants when applied to such yarns. A still further object is to provide yarn softening and lubricating formulas which can be readily removed from the yarns by the usual scour baths.

A still further object is to provide an improved method for the conditioning of yarns, particularly those composed of or containing organic derivatives of cellulose such as cellulose acetate,

whereby the yarn is rendered soft and pliable ing invention which, in its broader aspects, comprises the discovery that morpholine derivative having the general formula:

o-onR N(cH 0 CHg-CH: where a: and n are l, 2, 3, -etc., and R is a substituent selected from the substituted and unsubstituted aromatic, hydroaromatic, aliphatic and heterocyclic groups, 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 deriva tives of cellulose. We 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.

These compounds may be prepared by treating hydroxyalkylated morpholine derivatives with the desired acid, acid chloride, or anhydride by known methods. In case an acid is used, the compound may be esterified by removing water by means of an azeotropic withdrawing agent.

Examples of the preparation of typical compounds of this type are as follows:

PREPARATION or Es'mns Morpholine ethyl furoate 143 parts of furoyl chloride and a solution of 50 parts sodium hydroxide in 225 parts water are added simultaneously to 130 parts morpholine ethanol, with vigorous stirring. The temperature is kept at 15-20 by means of an ice bath. The mixture is thenstirred two hours, allowing the temperature to rise to that of the room. The resultant aqueous oil mix is then extracted twice with benzene (200 and. 100 parts). The benzene is distilled off at atmospheric pressure and the residue fractionated in vacuo. Morpholine ethyl furoate boils at 190-195/21 mm. It is soluble in water.

Morpholz'ne ethyl tetrahydrojuroate Morpholz'ne ethyl succinate 118 parts succinic acid, 120 parts morpholine ethanol, 150 parts toluene, and 1 part p-toluene sulfonic acid are distilled in such a way that the toluene is continuously separated from the water formed and returned to the reaction. The heating is discontinued when 18 parts of water have been collected. The solution is then treated with a small amount of sodium bicarbonate, filtered, and the toluene distilled off. The residue is then fractionated in vacuo. The ester boils at 250- 255/6 mm. It is water soluble.

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. We 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 asingredients of yarn conditioning or lubricating formulaes in conjunction with agents which function wholly or partially as lubricants.

In the following examples and description we have setforth several of the preferred embodiments of our invention, but they are included merely for purposes of illustration and not as a limitation thereof.

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

Example 1 The compound:

I CHr-GH: H:C-N

CHI-CHI 4 H-O-C OCi1 u m-o-c 0-0i1 u (N -Glycerol morpholine dioleate) Example 2 A conditioning liquid is made up as follows:

Parts o N -ClHr-OOOC11HSL so I (N-B-Hydroxy ethyl morphollne lam'ate) Olive oil and applied to textile materials such as silk, wool,

V cotton, viscose, cellulose acetate, etc. as described in Example 1. 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%. Cellulose acetate filaments or fibers treated as described are quite soft and pliable and give improved results in various operations such as weaving, knitting, etc. Other examples of suitable lubricants which are used as illustrated in Examples 1 and 2 follow.

Other examples of yarn conditioning composiyarns, particularly those composed of or containing cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, and similar cellulose organic acid esters in accordance with our invention and which render such yarns soft and pliable and especially well adapted for various textile operations, particularly knitting, are as follows:

Example 3 Parts /C rG 2 O\ N-CaHe-O C O--C4He 80 CHPCHQ (N -propanol morpholine valerate) Blown olive oil... 20

Example 4 E /0 H-CH: 0\ N-C:H4OCOCH3 20 (I) HC H2 C H3 (N-fl-hydroxy ethyl-3,5-dimethyl (morpholine acetate) Light mineral il Example 5 H2 H2 H2 H2 CC\ /CC\ 0 /N-CiH4-00 C-(CH2)2C O-O-CaHr-N /0 Ha Ha H2 H3 B-Hydroxyethyl morpholine succinate 20 Sperm oil 80 Example 6 Ha Ha C-C 0\ N-C H -O-OC-(CliflrCO OH CC H5 H3 'y-Hydroxypropyl morpholine adipale 50 Blown sperm oil- 50 Example 7 C2 4 0 \NC2H4O C1H4O o 00- 4o O 0 (N-fl-Hydroxy-B-ethoxy morpholine benzoate) Blown sperm oil. 60

Example 8 /GaH4\ OE:'N\ /O i can 2 H0 Q 0-GH:

(N-Glycerol morpholine acetate stem-ate) Neate-ioot 60 Oleyl alcohol 20 tions which may be applied to various types of arcane Example 9 /C2H4 CHZ CH2 I 0 'N-C2H4OCOCH CH2 20 CzH (N-fl-hydroxyethyl morpholiue tetrahydrofuroate) Dimethoxyethyl adipate 20 Blown neat's-ioot oil 60 Example 10 Wat r s0 CrHl CHr-O 0-0 C:H4N 0 10 C 2H4 (N-fi-hydroxyethyl morpholine acetate Water soluble cellulose ester Glycerol acetone.

and"

Example 11 (N- -hydroxyethyl morpholin ogate) is extruded through fine orifices into an evaporative atmosphere. The yarns thus produced are pliable and suitable for knitting, when prepared by being wound, or twisted and wound.

Any of the above compositions, 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 of the yarn. Yarn composed of cellulose acetate conditioned as described above gives excellent results when used in the circular knitting process.

As will be apparent from the above examples and description the conditioning agents of our invention may be applied by a wide variety of methods. For example, we 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, such as the particular cellulose derivative 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. Y

If the conditioning agent is to be applied to the yarn after spinning, this may be done by bringing the yarn in contact with a wick, roll, or felt wet therewith, or the liquid may be applied by immersion, spray, or otherwise. The particular point at which the liquid is applied may vary. It may, for example, be applied to the yarn inside or outside the spinning cabinet, between the guide and godet roll, between the godet or other roll or guide and the point of winding and/or twisting. In some cases, the liquid may even be applied to the yarn after winding onto cones, spools, bobbins, or the like or by the so-called bobbin to bobbin method. In the case of staple 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 vents, emulsifying agents, blending agents and the like, may be added within the scope of our invention. Likewise, various dyes or other coloring matter may be included in case it is desired to permanently or fugitively. tint or dye the material undergoing treatment.

Although we have found it convenient to illustrate our 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 ingredient. I

While we have described our 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 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 asto the conditioning of silk, wool, cotton, viscose and other natural or artificial materials. v

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 our 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, castor, neats-foot, sperm and other oils. 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 our invention possess many outstanding advantages. The fundamental and outstanding characteristic of the agents employed in accordance 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 amenableto 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 onthe 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 iri water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn conditioning agents and method of our 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 we 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 a N-hydroxy -alkyl morpholine ester.

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 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 a N-hydroxy alkyl morpholine ester.

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 a N-hydroxy alkyl morpholine ester and a textile lubricant.

5. Textile yarns amenable to textile operations including knitting, weaving, spinning and the like impregnated with a lubricant containing as its essential lubricating and softening component a N-hydroxy alkyl morpholine ester.

6. 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 a N-hydroxy alkyl morpholine ester.

'7. 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 a-N-hydroxy alkyl morpholine ester and a textile lubricant.

JOSEPH B. DICKEY. JANIES G. MCNALLY.