US2165353A - Yarn treating processes and compositions therefor - Google Patents

Description

Patented July 11, 1939 PATENT OFFICE YARN TREATING PROCESSES AND COMPO- SITIONS THEREFOR Joseph B. Dickey and James B.

Rochester, N. Y., aaslgnors Comp y, Rochester, N. Y.,

New Jersey Normington. to Eastman Kodak a corporation of No Drawing. Application November 26, 1937, Serial No. 176,698

18Glaims.

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 acetate propionate, cellulose acetate butyrate, etc., 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 fa cilitate handling in such operations as spinning, twisting, winding and reeling. In addition, it is necessary to treat the yarn'to adapt it for. use

' erations.

as warp or filling. or for thernanufacture ofvarions-types oflmitted fabrics. In knitting, it is particularly important that the yarn be-soft and pliable in order that it may conform readily to the contour ofthe needles and thus produce a closely knit fabric free from such defects as stitch distortion, "pin holes," ladderin and the like.

Eeretofore it hasbeen proposed to employ softening agents such as polyhydric" alcohols andsimllar agents as ingredients of yarn conditioning or lubricating formulas, generally in connectlon with mineral, animal or vegetable oils. It has been found, however, that most of the known softening agents and the variousformulae containingthem have certain drawbacks, one of the mostserlous 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 formulae. In addition, many of the known softening and lubricating agents are insufficiently 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 op- 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 lubricatlng formulae which can be readily. re-

moved from the by the scour baths.

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

whereby the yarn is rendered soft and pliable and capable of employment in a variety of textile operations where complicated designs or stitches are employed. Other objects will appear hereinafter.

These objects are accomplished by the follow ing invention which in its broader aspects comprises the discovery that acetal esters having the general formula:

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 derivatives of cellulose.

We have found that these compounds 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 a'solvent action thereon.

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 We have found that these compouds 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 formulae in conjunction with agents which function wholly or partially as lubricants.

In the following examples and description we have set forthseveral of the preferred embodi-. ments of our invention.- but they are. included merely for purposes of illustration and not as a limitation thereof.

The preparation of the above indicated class of compounds which we have found especially valuable as yarn conditioning agents may be carried out in known manner. An example of the preparation of a typical compound of this class is as follows:

Preparation of tetrahgdrofariural glycerol acc- 'tate.-l mol of tetrahydrofurfural glycerol and Example III: Percent Ethylidine glycerol methoxy acetate... Blown olive oil 40 Example IV:

Methyl ethyl ketone glycerol propionate- 70 Light mineral oil; 30

Example V; v v Propylidine glycerole lactate 30' Neats-foot oil 70 Example VI:

Cyclohexanone glycerol propiona 20 Blown neats-foot oil 80 Sulfonated olive oil 20 White. mineral oil...'.'.'. 10 Oleic acid 10 Ethanolamin 8 Water 7 Example VII: L

Butylioine glycemie ethoxy acetate 20 Sperm o 60 Laura] 30 Example VIII v Benzylidine glycerol lactate 50 Blown sperm oil 20 Sulfonated castor oil 30 on the steam bath for 7 hours. Fractionation of the solution gives the ester tetrahydrofurfural glycerol acetate having a boiling'point of 153-6 C. at 14 mm. in an 80% yield.

In an exactly similar manner there may be prepared tetrahydrofurfura'l glycerol propionate boiling at 162-167? C. at 16 mm. and tetrahydrofurfural butyrate boiling at l55-160'C.-at 8 mm.

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

Example I.-Yarn designed primarily for knit- I ting and composed of cellulose acetate is treated by applying .theretotetrahydrofl rfurylidlne' glycerol acetate. The amount of the conditioning liquid mayrun from 445% 'by weight of the untreated yarn. If the yarn is intended for weaving, the same procedure may be followed except that the amount of conditioning agent added to the yarn is only about l-%.

Example II.--A conditioning liquid is made up by mixing the following ingredients in the indicated proportions:

. Per cent -Glycerol acetone acetate '10 Olive oil 30 This composition is applied to a cellulose acetate yarn intended for knitting in an amount representing 4-25% by weight of the untreated yarn. The filaments or fibers treated with this composition are quite soft and pliable and give excellent results in textile operations, especially knitting.

tions which may be applied to various types of yarns, particularly those composed of or containing cellulose acetate, cellulose acetate propicnatc. and similar cellulose organic derivative yarns in such yarns soft and pliable and well-adapted for are the following:

Example IX.--A 20% solution of cellulose acetate in acetone in which is incorporated"1-35% Other examples of yarn-conditioning composi-- ments thus prepared are pliable and suitable for knitting.

Other examples yarn conditioning agents which may be employed in accordance with our invention are the following:

Example X: Per cent Water 80 Gelatin 5 Glycerol acetone acetate--- 10 Sulfonat'ed olive oil I 5 Emmple XI:

Water a 80 Water soluble cellulose ester 5 Ethylidine glycerol g1ycoiate a 10 Diethylene glycol 5 Example XII: Parts Blown teaseed oil Glycerol acetone propionate '15 25 Example XIII:

Teaseed oil I, 25 Oleic acid 25 Sulfonated castor oil Glycerol acetone acetate 20 30 Example XIV:

Blown neats foot oil 25 Cetyl sulfate ammonium salt 4 Oleie acid '20 Mineral oil I0 Glycerol acetone acetate 25 As will be apparent from the above examples and description, the conditioning agents of our invention may be. applied by! wide variety of 9 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 derlvatlve used in making the yarn, the solvent or solvent combination used in making up the spinning solution, and the degree of softness or pliabllity desired in the yarn, etc.

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. so It may, for example. be applied to the yarn inside or outside the spinning cabinet, between the I guide and godet roll, between the godet or other roll or guide and the point of winding and/or twisting. In, some caseszthe 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 iiber manufacture the liquid may be applied to the yarn prior to, or after cutting into staple le xths. v

111e amount of the scent so employed will vary widely depending upon the results desired, the

by weight,'based on the weight of the dry yarn, u

f the above compositions, we have found that those of Example VI and VII, characterized by the presence therein of cyclohexanone glycerol propionate and benzylidine glycerol lactate, respectively, and those of Examples X, XIII and XIV, characterized by the presence therein ofglycerol acetone acetate are unique in their abiiity to reduce or eliminate accumulations of static electricity on yarns of the type herein referred to, particularly when such yarns are employed for the manufacture of cut staple fibers. It is therefore one of the specific features of our invention to employ these compositions as anti-static agents generally, and specifically for the manufacture of cut staple yarns. In producing cut staple fibers, the selected composition may be deposited on the fiber after the cutting operation in any convenient manner, as by a conventional type of applicator, by spray, immersion or the like. Cut staple fibers treated in this manner display a very marked reduction in their tendency to accumulate charges of static electricity and in many cases this tendency is substantially or completely eliminated. I

Although in the above examples we have referred primarily to yarn treating compositions containing. only the conditioning agent and an;

oil, other ingredients such as solvents, non-solvents, 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 desiredto permanently or fugitively tint or dye the material undergoing treatment. I

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.

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 formulaedesc'ribed herein are applicable to the condition of many other types of cellulose derivative yarns such as those "composed of or containing cellulose propionate, cellulose butyrate, celluloseacetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to the condition 'ing 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 up a variety of yarn treating formulae of varying composition.

The yarn conditioning method and compositions of our invention possess many outstanding advantages. characteristic of the agents employed in accordance with the invention is their ability to soften yarns, especially those composed ofor contain-- ing 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 thesecompounds 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 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 '3 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 weclairn and desire to secure by Letters Patent of the United States 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 sisting of hydrogen, part of a cyclic chain of carbon 'atoms, alkyl, aryl, and heterocyclic groups; and wherein in R a substituent of the group consisting of hydrox'y and a'lkoxy groups may replace hydrogen. Y

'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 softeningcompound 'acetal esters having the formula:

The fundamental and outstanding are substituents selected from the group consisting of hydrogen, part of a cyclic chain of carbon atoms, alkyl, aryl, and heterocycllc groups; and wherein in R a substituent of the group consisting of hydroxy and alkoxy groups may replace hydrogen.

- 3. The process 01! conditioning yarn composed or 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 soitening component an acetal ester having the "formula:

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 acetal esters having the formula:

7 I where R is a substituent selected from the group consisting of hydrogen and alkyl; R and R'fiare substituents selected from the group consisting of hydrogen, part of a cyclic chain of carbon atoms, alkyl, aryl, and heterocyclic groups; and wherein in R a substituent of the group consisting of hydroxy and alkoxy groups may replace hydrogen.

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 acetone acetate.

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 ethylidine glycerol methoxy acetate.

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 methyl ethyl ketone glycerol pr'opionate.

8. A conditioning agent for rendering yarns more amenable to textile operations including knitting, weaving,. spinning and the like which comprises acetal esters having the formula:

7 RI! R! where R is a substituent selected from the group consisting of hydrogen and aikyl; R. and R" are substituents selected from the group consisting of hydrogempart ot a cyclic chain oi carbon, atoms. alkyl, aryl, and heterocyclic groups; and wherein in R a substituent oi the group consisting 0! hydroxy and alkoxy groups may replace hydro- 9. 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 acetal esters having the formula:

RI! n! where R is a substituent selected from the group consisting of hydrogen and alkyl: R and Rf are substituents selected from the group consisting of hydrogen, part of a cyclic chain of carbon atoms, alkyl, aryl, and heterocyclic groups; and wherein in R a substituent oi the group consisting of hydroxy and alkoxy groups may replace hydro gen.

10. A conditioning agent for rendering yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning and the like containing glycerol acetone acetate.

11. A conditioning agent for rendering tentile yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning and the like containlng ethylidine glycerol methoxy acetate;

12. A conditioning agent for rendering textile yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning and the like containing methyl ethyl ketone glycerol propionate.

13. Textile yarn amenable to textile operations including knitting, weaving, spinning and the like impregnated with a lubricant containing acetal esters having the formula:

' consisting of hydrogen and alkyl; R and R are suhstituents selected from the group consisting of hydrogen, part of a cyclic chain of carbon atoms, alkyl, aryl, and heterocyclic groups; and wherein in R a substituent of the group consisting of hydroxy and alkoxy groups may replace hydrogen.

14. Textile yarn composed of or containingpb ganic derivatives 01' cellulose amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a conditioning I where R is a substituentselected from the group consisting of hydrogen and alkyl; R and R." are substituents selected from the group consisting of hydrogen, part-of a cyclic chain of carbon atoms, alkyl, aryl, and heterocyclic groups; and. wherein in R a substituent of the groupconsisting of filil hydroxy and aikoxy groups may gen.

15. Textile yarn 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 acetal esters having the formula:

replace hydroincluding knitting, weaving,

like, impregnated with a lubricant comprising where R is a substituent selected from the group consisting 0% hydrogen andalkyl; R. and R', are substituents selected from the group consisting vo! hydrogen, part of a cyclic chain of carbon atoms,

' alkyl, aryl, and heterocyclic groups; and wherein in R a substituent of the group consisting of hydroxy and alkoxy groups may replace hydrogen.

16. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising glycerol acetone acetate.

1'1. Textile yarns composed of or'containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising ethylidine glycerol methoxy acetate.

.18. Textile yarns composed of or containing cellulose acetate amenable to textile operations spinning and the methyl ethyl ketone glycerol propionate.

JOSEPH B. DICKEY. JAMES B. NORNIINGTON.