US2318296A - Antistatic agent and its application - Google Patents

Description

Patented May 4, 1943 ANTISTATIC AGENT AND ITS APPLICATION Joseph B. Dickey, Rochester; N. Y., assignor to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application December 23, 1940, Serial No. 371,402

12 Claims. CL 8-1425) This invention relates to the treatment of cellulose organic derivative filaments, fibers, threads and the like and more particularly to a method of eliminating the tendency of such materials to accumulate charges of staticelectricity in twisting, winding and spinning. The invention also relates particularly to the treatment of cellulose organic derivative cut staple fibers to adapt them for the manufacture of spun yarns.

As is well-known, cellulose organic derivative materials, particularly in filament, yarn, or sheet form, are particularly subject to the accumulation on their surfaces of charges of static electricity from frictional and other influences. In the case of filaments and yarns in which the surface area of the material (per unit of weight) is enormously greater as compared to sheets or films, the problem of static often assumes serious proportions. In the manufacture of yarns of various types from artificial filaments, numerous steps in which the yarn is subjected to frictional influences may be necessary. as for example. twisting, winding, warping, carding, combing, drawing, spinning and the like, all of which operations tend to produce large accumulations of static on the filaments. This is particularly aggravated in the utilization of cut staple, as for example, in the making of spun yarn, since in carding and combing considerable friction is de veloped and as a result sufiicient charges accumulate on the fibers to make the formation of the web difiicult, if not impossible; furthermore, even if a web is formed with some degree of success, the subsequent drafting operation produces a very uneven spun yarn or intermediate roving due to the presence of the static charge. In addition, there is the ever-present fire hazard.

Cellulose derivative yarn, particularly. in the form of cut staple, is extremely difiicult to handle in the various operations involved in making spun yarn, not only because such material is composed of filaments having smooth, glass-like surfaces without natural'kink or irregularity, but also because it has relatively negligible moisture content at normal humidities, as compared to natural fibers such as cotton and wool, making it inherently far more susceptible to the accumulation of static. The charges accumulating on cellulose derivative cut staple fibers, are,.under some circumstances, even sufficient to separate the individual fibers a distance of inches, notwithstanding their relatively minute size.

This invention has as its principal object to provide an improved method for the treatment of cellulose organic derivative yarns to reduce or eliminate the tendency of such yarns to accumulate charges of electricity under frictional and other influences. A further object is to provide a method of facilitating the handling and employment of cellulose organic derivative cut staple fibers in the various operations involved in the manufacture of spun yarns. A still further object is to provide a method of treating cellulose organic derivative yarns in either filament or cut staple form, wherein the material is simultaneously softened and lubricated and the accumulation of static charges thereon is prevented. Another object is to provide an improved type of cellulose organic derivative cut staple having little or no tendency toward accumulation of static electrical charges. Other objects will appear hereinafter.

These objects are accomplished by the following invention which, in its broader aspects, comprises applying to cellulose organic derivative yarns either in the form of filaments, threads, or stable fibres, an antistatic composition characterized by the presence therein of phosphoric, phosphorus, and sulfuric acid esters of alcohols having the general formula:

wherein R is an alkyl radical selected from the I group consisting of methyl, ethyl, butyl, amyl,

hexyl, cyclohexyl, allyl, octyl, lauryl, cetyl, oleyl,-

hydroxy ethyl, naphthenyl, tetrahydrofurfuryl. decahydronaphthol, triethylene glycol, Carbitol (the trade name for the monoethyl ether of diethylene glycol), etc, and a: is 0, 1, 2, etc., and Z is a mono-valent substituent selected from the group consisting of alkyl, hyd'roxyl, aryland the PREPARATION OF COMPOUNDS These esters may be prepared as described in the well-known method of Guerbet. The preparation of many of the alcohols is described in an article appearing in the J. Soc. Chem. Ind., 56, 587 (1937), the esters being prepared by wellknown methods as will be illustrated by the following examples.

SULFATO Esrrns Example 1 156 g. 2-butyl cyclohexanol are dissolved in chloroform and 120 g. of chlorosulfonic acid are added slowly with stirring. The reaction starts at once as is evidenced by the evolution of hydrogen chloride. The reaction product, which is 2-butyl eyclohexanol sulfate, is heated to complete the reaction and drive of! hydrogen chloride. When the reaction is complete, the chloroform is distilled off and any desired salt prepared, such as Na, K, NH4, Ca, ethanolamine-mono-, di-, or tri-, butylamine, di-amylamine, tri heptylamine, cyclohexylamine, aniline, diethyl cyclohexylamine, piperidine, morpholine, oleylamine, tetrahydrofurfurylamine, benzyl trimethyla-mmonium hydroxide, naphthenylamine, etc.

Example 2 I 190 g. 2-benzyl-cyclohexanol are dissolved in pyridine and sulfated with 120 g. chlorosulfonic acid as described above. The reaction product is 2-benzylcyclohexanol sulfate. Similar salts may be prepared as described above.

Example 3 n cm-c-cm H-CH: .g. a.

cc-on CrHn are treated in the cold with 135 g. sulfurylchloride and the reaction is completed by warming. The free acid, (2-amyl-4-isopropyl cyclohexanol sulfonic acid) or its sodium salt can be prepared by adding water, or water and alkali. If desired, we may prepare amides or substituted amides from the acid chlorides. Thus, by treating with ammonia CsHii CH: CH:--- H secs tiMLNH. C a OH:- H: L!

(2-amyl-4-isopropyl cyclolieranoi sulfamate) is prepared.

Example 4 By using sulfuric acid and GHQ-CHI C a CHOH cn-c HI (B31111 (Z-octyl-Zi-butyl cyclohexanol sulfate) i prepared.

Example 5 Using methods similar to these described above, there may be prepared:

5 CHa-C H CH1 CH-O-SOaOH CHr-C H CH; CH:

H1 H; C a

16 (2-cycloliexyl cyclohexanol sulfate) H: CH:

l CHr-C-H ZH-C-O-SOg-OH 20 H, lIz-totrahydrofurluryi (2-tetreliydrolurfuryl4,6 dimethyl cyclohexyisulfate) CHr-CH:

CoHs-C (EH-0801011 CHr-C H CaHr-O C:H(0 CiHl (Z-beta-ethoxy-beta-othoxy-ethyi-l-phenyi cyclohexyl sulfate) CHI-CHI V (ll Ii OHO-S0:0H

CHr-CE CiaHu (ii-lauryi cyclohexyi sulfate) GHQ-CH] C s GHQ-80:0 CHs-C-CuHa (2-cetyl cycloiieryl sullate) GHz-CH: 5 C CH-OSOzOH CH|CH-CilHu (Z-oleyl cyclohexyl sulfate) CHr-C H;

CH: QH-OSOaOH CHr-C CIIHIF-BOIHOH -(2(liydroxy sulfate) oetadecyl cyclohexyl sulfate) CHa-CH:

Ca CH0 8 01H CH:C

CuHaP-OH .60 (Z-hydroxy decyl cyclohexyl sullate) etc.

Pnosrnn'o AND Pnosrmro Earns Example 6 170 g. 2-amylcyc1ohexanol are dissolved in chloroform and treated in the cold with 154 g. phosphorus oxychloride. The product is 2-amyl cyclohenlphosphate. The reaction starts at once as is evidenced by the evolution of hydrogen chloride. The recation is completed by warming. Nitrogen may be passed through to aid in removing the hydrogen chloride. The free acid or sodium salt is prepared by adding water or water 76 and alkali of the necessary amount. Amine salts of the types indicated in Example 1 may be prepared. Various amide derivatives may be prepared by treating the acid chloride with ammonia. Thus,

CIII-C H:

C H: C H-- I CH:Cl I N 1h (2-hexylcyclohexyl phosphnmate sodium salt) ONa H (Mir-CH N-(dio C H: C H-O P I! \H C Ir-(7H 0 N-C (HI CnHn (Z-lauryl cyclohexyl bishutyl phosphaniuie) GHQ-CH! S.ONH|

C II, C H 0- P l C ]IzC H S N-morpholinc iiaphthenyi (Z-naphthenyl cyclohexyi thio-phosphaie morphnmatc ammonium t) Example 7 204 g. Z-beta-phenylethyl cyclohexanol are dissolved in pyridine and phosphated with 163 g. C2H5OPOC12 by adding the acid chloride and warming to 50. The acid chloride is hydrolyzed and the desired salt prepared as in Example 6. In a similar way we may prepare:

156 g. 2-butylcyclohexanol are heated in dioxane with one equivalent of P205 at 100 for 6 hours.- The product has the formula:

action. The resulting dichloride, after evacuation to remove hydrogen chloride, is then treated with cold aqueous sodium carbonate. and the compound Y /Cg: /H /0Na cm c-or g: -H ONa C a Call:

(Z-butyi cyclohaxyi disodium phosphita) is formed.

By neutralizing the salt with mineral acidand then treating with the desired base. any desired organic base salt can be prepared.

Example 10 One mole of CH] ch, CH--0 (l 11, 11-0.! CHa is heated on a water bath with one mole of pyridine to give Ah. 0 o

CH: I

(Z-butyl cyciohexyl sullcnium pyridinium chloride) Example 11 One mole 2-cetyl-4-isobutyl cyclohexanol is reacted with one mole phosphorous trichloride as previously described. The acid chloride is bydr01yzed with 1.5 moles sodium carbonate and the 2-cetyl-4-isobutyl cyclohexyl phosphorous acid is filtered off. Any desired salt as indicated in the previous examples can be prepared. Similarly, there may be prepared compounds such as 2-oleyl cyclohexyl phosphite, 2,4,6-tri-isopropyl cyclohexyl phosphite, 2,4-di-isobutyl cyclohexyl phosphite and 2-beta-ethoxy-beta-ethoxy ethyl cyclohexyl phosphite, etc. I

In like manner, pyrophosphoricacid or tetrapyrophosphoric acid may be used as phosphating agents in a manner similarto the use of the phosphating and phosphiting agents referred to in the above examples.

In accordance with my invention the abovementioned compounds may be applied to the yarn in any convenient manner, for example, by roll,

. wick, immersion, spraying or the like. Inasmuch as these compounds are soluble in oil they may be dissolved or dispersed in oils such as mineral oil, blown and unblown, drying and semi-drying.

Example 12 o (2 butyl cyclohexanol phosphate bisdiethylcyclohexylemine salt) is applied to textile materials (silk, cotton, wool, viscose, cellulose acetate, etc.) by means of a wick, roller, spray, etc., to facilitate their knitting, weaving, spinning and the like. Yarns lubricated with the above types of lubricants are of special value in the preparation of cut staple fibers. These fibers may be oiled before or after cutting.

Example 13 o [W 1' CH-O S0H-Ditetrahydrofuriurylamine is applied to textile materials as in Example 12 CH: CH-CsHn C H C H:

(l-amyl-i-methyl cyclohexanosaiiigate ditetrehydroiuriurylamine Conditioning liquids particularly useful for the treatment of various types of yarns in accordance with my invention particularly those composed of or containing cellulose acetate, cellustaple fibersmade of cellulose acetate and which may be used for other textile operations follows:

Parts CHr-CH: 5

C H: /C II-O P-O H-(HzN C4110):

cur-TH 0 0H (2 bcnzyl cyclohexanol phosphate bisdibutylamine salt) 5 Olive oil 95 Example 16 Parts C HrC H-CnH1: ll 2 'CHr- H- H0S-0 H-naplithcnyl amine CH:- H:

(2-hexyl-p-methyl cyclohexanol-sulfutc naphthenylamine salt) ".2.-- 5 Glycerolacetone propionate- -70 Blown olive oil 65-25 Example 17 Parts CH -C ii 30 2 2 O H CH: CH-0 P .(CzHshN-Cdlu C Hr-CH 0 ii CnHzs (2-lauryl cyclohcxanol phospliite (licthyl-cyclolicxyluminc salt) lose acetate ro ionate, cellulose acetate buty- Neats-foot oil 95 rate, and similar organic acid esters, and especial- Example 18 ly adapted for the deelectriflcation or anti-static Y Parts treatment of cellulose organic derivative cut Cm cm 0 staple yarns are as follows: H

CH2 CII-O S-S H.1n0rph0iinn Example 14 CH C II I Parts 1 2- H O Dioxane dioleyl ether 80 CIBHJJ as-tetrahydrofurfuryloxyethyl ether 10 (2-c/etylcyclohexanolthiosuliaie morpholincsalt) Blown neats-foot oil III: 95 0 P0Na OH I Example 19 Parts cfi, CHCoHn carom cim (1H1 H: /CH-0 -OHN-fiyclohexyi GH-CuHn r- CzHs (2-hexylcyclohexanol phosphate monocthyl ester sodium salt) li lI! Water g (Z-hexyl cyclohexanol sulfate diethyl cyciohexylamine salt) "f T f 5-10 and applied to textile materials such as silk, wool, Mineral i1 30 cellulose acetate, etc., as described in Example Blown olive 1L 12. If the yarn is intended primarily for knito (55-60 ting, the amount of conditioning liquid applied Eiwmple 20 may vary from 4-25 per cent by weight of the Parts yarn and if for weaving, between 1-5 per cent S L by weight.

.Cellulose acetate filaments treated as described above are quite soft and pliable and give im- C 1 CH OH-Bcnzyl trimcthyl ammonium proved results in various textile operations such carom hylmxde as weaving, knitting, etc., and especially in the CH J on production of cut staple yarn. Other examples of suitable lubricating mixtures having antistatic 7 0 properties which are used as illustrated in Ex- (memhydrf f 1 01 h h amples 12 and 13 follow: benzyl m-.Ztgii;ifiimflifihttdrliiiiti bumamm Example 15 Sperm n 2 A conditioning liquid particularly useful on cut Tetrahydrofurfuryl lactate i 30 Em le 21 Example 26 Ont-CHI Blown olive 80-99 cm-cn, orLHN-Clh- H 3' 5 cm-c ir, out no-c CH0I|\ 0 0%, cH'0P /CHC J) 0H.Dicyclohexy1emlne cu -c o'Ne cm. 04H He h h t m (2-emyl yclohexanol disod' ium phosphite) ol h l a e e yehii -y fii'iegfiieyeie giimdfifiiti -1 v 5 Exam le 22 Blown sperm oi 60 Parts Mineral nil I 35 15' CHr-CH: /01I E l 22 C CH-OP 'Diethylcyclohexylamine Parts cu -0 OH Di-beta-methoxy ethyl succinate 30 H.

CHFCH' z-tti clhx lhshitedithl 1h 1' it C a OH0I l 0H-trlethanolamine trlacetate I u y W o p o P e y cyco exy ammesfqy) CHr-C 0 I 1-15 HPCHQHFCH Any of the above compositions may be applied i h It H t t it (2 any] cyclohmnol Mm am I mm a e J 25 to the yarn intended for use in circular knitting by means of a bath, wick, spray, roller, pad or Teaseed oil 64-55 any suitable means. The amount of condition- E Z 23 ing liquid applied may vary between 5-25% by j 8 Parts weight of the yarn. Usually, however, the amount 1 90 99 of conditioning liquid applied'is about 10-15% Mineral by weight of the yarn. Yarn composed of cellu- CHI-CHI lose acetate conditioned as described above gives 0 cn-o P Dicthanolamine excellent results when used in the circular knitting process. CHFC OH 0M As will be apparent from the above examples ciHr-0ciHiOCiHr and description the conditioning agents of my h e a invention may be applied by a. wide variety of Q- -P 1 -9 methods. For example, we may employ the agent gaaymfitthyl cyclohexyl phosphite diethsnol v as an ingredient of the Spinning dope from which 140 40 filaments are formed, the amount of the agent u so employed depending upon a number of fac- Example 24 tors, such as the particularcellulose derivative Parts used in making the yarn, the solvent or solvent C H combination used in making up the spinning so- CHPCH z s lution, and properties desired in the finished on, 011-0 s 0ioH-HN yam. em

c,i1.0cm If the conditioning agent is to be applied to C an the yarn after spinning. this may be done-by m bringing the yarn in contact with a wick, roll, (2-octndecyl cyclohexauol sulfate di-beta-methoiy othylomines t) or felt wet therewith, or the liquid y be 5 plied by immersion, spray, or otherwise. The oleic acid 20 particular point at which the liquid is applied may vary. It may, for example, be applied to f the yarn inside or outside the spinning cabinet, CetylsulfateN cyclohexylamin between the guide and godet roll, between the CHB godet or other roll or guide and the point of 5 winding and/or twisting. In some cases, the liq- 2 uid may even be applied to the yarn after wind- Sodium Sulfa 68 ing onto cones, spools, bobbins, or the like or by Blown teaseed the so-called bobbin'to bobbin method. In the Example 25 case of staple fiber manufacture, the liquid may P t be applied to the yarn prior to, or after cutting Water 70 into staple lengths.

nulo ester 5 The amount of the agent so employed will vary water Soluble ca 58 65 widely depending upon the results des1red, the CHI-CH] 0H specific nature of 'the material to which the 1 agent is applied, the use to which the yarn is eventually to be put and other factors. For ex- CHPCH f g ample, in a given case where a cellulose organic fl -7 7 acid ester yarn such as a yarn composed of CHPCH, cellulose acetate, is intended for knitting, about 4 to 25% or more by weight, based on the weight (2-beta-morpholino ethyl cyclohexanol phosphite) o t e d y y y be satisfactory, w le if the 5 yarn is intended for weaving, the amount may sulfonated castor oil 10 vary between about 1 and 5%.

Although in the above examples I have refrred 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 my 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 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 thedeelectriiying 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 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 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 individualstrands 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 lmblown, 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 agents of my invention also have exceptional value as surface-active compounds and as such may be employed as wetting agents, emulsifying and dispersing agents, textile assistants, dye dispersing agents and the like.

The yarn conditioning method and compositions of my invention possess many outstanding advantages. The fundamental and outstanding characteristics of the agents employed in accordance with the invention is their ability to deelectrify yarns, especially those composed of or containing organic derivatives of cellulose such as cellulose acetate and render them amendable to various textile operations, especially operations such as those involved in the manufacture of out staple fibers, as well as in weaving and knitting. 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 by means of the usual aqueous scour baths.

Of the above compositions I have found those of Example'l, the fifth composition of Example 5, and Example 6 as of outstanding value for the purpose of my invention.

What I claim and desire to secure by Letters Patent of the United States is:

1. The method of eliminating the tendency of yarns, filaments or fibers to accumulate charges of static electricity, which comprises applying thereto prior to any. textile operation thereon a composition containing as its essential anti-static component an ester of an alcohol selected from the group consisting of the phosphato, phosphito and sulfate esters of alcohols, said alcohols having the general formula:

ch, n i

wherein R is an organic radical selected from the group consisting oi! methyl, ethyl, butyl, amyl, hexyl, cyclohexyl, allyl; octyl, lauryl, cetyl, oleyl, hydroxy ethyl, naphthenyl, tetrahydrofurfuryl, decahydronaphthol, triethylene glycol, and monoethyl ether of diethylene glycol, and a: is 0 or an integer not over 3, and Z is a mono-valent substituent selected from the group consisting of alkyl, hydroxyl, and aryl.

2. The method of eliminating the tendency of yarns, filaments or fibers composed of or containing organic derivatives of cellulose, to accumulate charges of static electricity, which comprises applying thereto prior to any textile operation thereon a composition containing as its essential anti-static component an ester of an alcohol selected from the group consisting of the phosphato, phosphito and sulfato esters of alcohols, said alcohols having the general formula:

wherein R is an organic radical selected from the group consisting of methyl, ethyl, butyl, amyl, hexyl, cyclohexyl, allyl, octyl, lauryl, cetyl, oleyl, hydroxyl ethyl, naphthenyl, tetrahydrofurfuryl, d'ecahydronaphthol, triethylene glycol, and monoethyl ether of dietlwlene glycol, and a: is 0,

,- or an integer not over 3, and Z is a mono-valent substituent selected from the group consisting of alkyl, hydroxyl, and aryl.

3. The method of eliminating the tendency of yarns, filaments or fibers composed of or containing cellulose acetate to accumulate charges of static electricity, which comprises applying thereto prior to any textile operation thereon a. composition containing as its essential anti-static component an ester of an alcohol selected from the group consisting of the phosphato, phosphito and suliato esters of alcohols, said alcohols having the general formula:

H: C\ /H 1150 C wherein R is an organic radical selected from the group consisting of methyl, ethyl, butyl, amyl, hexyl, cyclohexyl, allyl, octyl, lauryl, cetyl, oleyl, hydroxv ethyl, naphthenyl, tetrahydroiuriuryl, decahydronaphthol, triethylene glycol, and monoethyl ether of diethylene glycol, and a: is or an integer not over 3, and Z is a mono-valent substituent selected from the group consisting of alkyl, hydroxyl, and aryl.

4. The method of eliminating the tendency of yarns, filaments or fibers composed of or containing organic derivatives of cellulose to accumulate charges of static electricity, which comprises applying thereto prior to any textile operation thereon a composition containing as its essential anti-static component 2-butyl cyclohexanol sulfate.

5. The method of eliminating the tendency of yarns, filaments or fibers composed of or containing organic derivatives of cellulose to accumulate charges of static electricity, which comprises applying thereto prior to any textile operation thereon a composition containing as its essential anti-static component 2-cetyl cyclohexyl sulfate. 4

6. The method of eliminating the tendency of yarns, filaments or fibers composed of or containing organic derivatives oi! cellulose to accumulate charges of static electricity, which comprises app ying thereto prior to any textile operation thereon a composition containing as its essential anti-static component 2-amyl cyclohexyl phosphate.

'7. Textile yarns having a lessened tendency to accumulate charges of. static electricity, said yarns containing an ester of an alcohol selected from the group consisting of the phosphato, phosphito and suliato esters oi alcohols, said alcohols having the general formula:

wherein R is an organic radical selected from 8. Textile yarns composed of or containing organic derivatives of cellulose having a lessened tendency to accumulate charges of static electricity, said yarns containing an ester of an alcohol selected from the group consisting of the phosphato, phosphito and sulfate esters of alcohols, said alcohols having the general formula:

wherein R: is an organic radical selected from the group consisting of methyl, ethyl, butyl, amyl,

hexyl, cyclohexyl, allyl, octyl, lauryl, cetyl, oleyl,

hydroxy ethyl, naphthenyl, tetrahydrofurfuryl, decahydronaphthol, triethylene glycol, and monoethyl ether oi diethylene glycol, and a: is 0 or an integer not over 3, and Zis a mono-valent substituent selected from the group consisting oi allwl, hydroxyl, and aryl.

9. .Textile yarns composed of or containing cellulose acetate having a lessened tendency to accumulate charges. of static electricity, said yarns containing an ester of an alcohol selectedfrom the group consisting of the phosphato, phosphito and sulfato esters of alcohols, said alcohols having the general formula:

H I Rio 0 Cfia \H wherein R. is an organic radical selected from the group consisting of methyl, ethyl, butyl, amyl, hexyl, cyclohexyl, allyl, octyl, lauryl, cetyl, oleyl, hydroxy ethyl, naphthenyl, tetrahydrofurfuryl, decahydronaphthol, triethylene glycol, and monoethyl ether of diethylene glycol, and :c is 0 or an integer not over 3, and z is a mono-valent' substituent selected from the group consisting of alkyl, hydroxyl, and aryl.

10. Textile yarns composed of or containing organic derivatives of cellulose having a lessened tendency to accumulate charges of static electricity, said yarns containing 2-butyl cyclohexanol sulfate.

l1. Textile yarnscomposed of or containing organic derivatives of cellulose having a lessened tendency to accumulate charges of static electricity, said yarns containing 2-cetyl cyclohexyl sulfate.

l2. Textile yarns composed of or containing organic derivatives of cellulose having a lessened tendency to accumulate charges of static electricity, said yarns containing 2-amy1 cyclohexyl phosphate.

JOSEPH B. DICKEY.