CA1051019A - Random copolymers of polyoxyethylene polyoxypropylene glycol monoester, process of making the same and textile fiber containing the same - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE

A textile fiber lubricant, namely random copolymers of polyoxyethylene polyoxypropylene glycol monoester produced by the condensation reaction of an aliphatic fatty acid, or acids having from about 8 to about 22 carbons in the chain, with a mixture of ethylene oxide and propylene oxide, in the presence of an alkali catalyst. These fatty esters are water soluble, biodegrad-able and exhibit superior lubricating properties when applied to synthetic fiber.

The esters have the empirical formula:

R-?-O-(M)H
wherein R is an aliphatic chain having from about 7 to about 21 carbon atoms and M is a random mixture of oxyethylene [-CH2?CH2?O-] and oxypropylene {-CH2?CH(CH3).O-] groups.

Description

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~ RANDOM COPOLYMERS OF POLYOXYETHYLENE POLYOXYPROP~LENE GLYCOL ;~
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.. MONOESTER, PROCESS OE~ MAKING THE SAME AND TEXTILE FIBER
j CONTAINING THE SAME
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.~j . . , .~ BACKGROUND~OF THE INVENTION ~

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jField of the Invention:
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' This invention relates to textile lubricants and ~: :
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`i5 more particularly concerned with random copolymers of polyoxyethylene polyoxypropylene glycol monoester and a process o.~ producing the same. The invention is also concerned with a lubricated synthetic fiber.
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Descrip-tion of the Prior Art:

I am aware of U.S. Patent No~ 3,770,701, ~. S.
Patent No. 2,620,304 and ~.S. Patent No. 2,457,139 which I consider to be the most pertinent references. I am the co-inventor of the surfactant described in U.S Patent No. 3,770,7Ql.

It is well-known that essentially all synthetlc textile fibers as originally produced cannot be processed ~;
into yarn and fabric in textile mills because of snagging, clinging and breaking that results from a lack of lubrication and/or static electricity. These processing difficulties, `~
however, are usually overcome by the application of "textile lubricants" or "fiber finishes" to the fibers.

The traditional fiber finishes used on synthetic textile fibers are made up of three components. The first ingredient is the basic lubricants. Most widely used for the lubricant is either a mineral oil or a fatty ester -~ (e.g~ butyl stearate)~ The second ingredient is an anti~
- static agent to reduce static electricity which is common to nearly all synthetic fibers and especially those with low moisture regain properties. Anti-static agents are ~` generally of the cationic (~uaternary amine or imidazolinium . ~ :
salts) or anionic type ~salts of partial esters of phosphoric ~1 ; acid~. The third ingredient, is the emulsifying agent. It is necessary to use an emulsifying agent since an even application of finish components is best achieved from a `` - ''' :~.~

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dilute aqueous emulsion Emulsifying agents commonly employed are nonionic (polyoxyethylene ethers and esters) or anionic (salts of akyarylsulfonic acids). The patent to Fortess, et al, U.S~ Patent No. 2,730,498 discloses a typical finish.

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The lubricants used heretofore have many drawbacks, `
but chief among them is their volatility. In other words lu~ricants have objectionable vapors which are released in the area around the yarn or fiber drying equipment.

Water insolubility of mineral oil and fatty ester lubricants is another problem. When a lubricant is water -insoluble it is usually difficult to apply to the fiber.
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To overcome this, the lubricant is emulsified with the :,:
water. The nonuniformity and instability of these emulsions ~` frequently results in the uneven application of the lubricant , :
~; to the fibers. Processing problems usually result from this uneven application. Even when excellent emulsions are ~ `
prepared, the relatively large proportion of emulsifying~
agent necessary in the emulsion has a negative effect on f ~ 20 the lubrication of the fibers.
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Another problem with oily lubricants is that they are difficult to remove from the fibers after these fibers have been processed into textile yarn or fabric. The scouring of these oil bearing fabrics must be thorough and complete since spotty and uneven dyeing of the fabrics and poor hand : ~ . ., ' ~`

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characteristics will result.

Still another problem is that the lubricant must be disposed of after it is scoured off. Disposal, by way of sewering at the textile mill, results in an oil film or slick in nearby streams and ponds. This oil is only very ~ ~
slo~ly decomposed by bacteria, if at all. ~ ~;

In the past, attempts have been made to overcome ;
the problems described above by using fatty esters of poly-oxyethylene glycols, as the lubricants or emulsifiers.
These attempts have met with limited success in some special circumstances. The failure of these products to completely : ~
resolve the difficulties, results from the nature of the ~ ;
materials involved. In order to achieve good lubrication ~;~
from the fatty acid portion of the product, it is necessary for the fatty hydrocarbon chaln to be as long as feasible, at least eight carbons long and preferably greater than twelve~ In order to make esters of such acid water soluble, `~
it is necessary to employ proportionately longer polyoxy-ethylene glycol chains. This results in pasty solid products - : .
or high viscosity liquids which are too thick for use in the high speed processing of textile fibers.

Surfactants and lubricants are ~nown having an aliphatic alcohol or carboxylic acid and a series of oxyethylene groups, as for example U.S. Patent No. 2,457,139 to Fife, et al. However, such compounds are generally speak-ing unsa~isfactory for high-speed textile fabrication uses, ~
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have insufficient hydrocarbon chain contellt~ The problellls described above are believed to be overcome by the lubricants of the present invention~

SU~RY OF THE INVENTION

Briefly described, an aspect of the present invention includes the process of comingling a fatty acid or acids with a mixture of ethylene oxide and propylene oxide under condensation reaction conditions to produce a fatty ester having an alipha~ic chain containing 8 to 22 carbons. 'l'he resultant lubricant has superior lubricating properties and is readily and easily applied to synthetic fibers, it being water soluble, liquid at rOoM temperature, and biodegradable.
More particularly, the process comprehends the prep-aration of a liquid, water soluble, biodegradable, textile fiber lubricant comprising, condensing from approximately 40% to approximately 75~, by weight, ethylene oxide, from approximately 10% to approximately 40% by weight propylene -oxide and Erom about 18~ to about 35~j by weight, a fatty ~ acid having from about 8 to about 22 carbons, the ethylene oxide being in proportion to the propylene oxide by weight rom about 1.0:1 to about 7.S:1, in the presence of an alkaline catalyst. Preferably the process includes heating the condensation reactants to a temperature of between about .: ~
110C and about 180C at pressures up to about 100 psi for ; from about 4 to about 8 hours. Exemplary fatty acids are ones derived from coconut oil, and hydrogenated tallow.

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Another aspect of the invention is a compound which ~ -;
is a liquid water soluble and biodegradeable and may be used as a textile lubricant for synthetic fibers and is inexpensive to manufacture, easily handled, readily applied to the fibers --and efficient in operation.
The compound which may be used as a lubricant for synthetic fibers and under normal conditions requires no external heating, in use, storage or transfer and will not readily separate during bulk storage over an extended period of time. Further such compound provides a synthetic fiber lubricant which is stable at fiber drying temperatures and does not readily steam distill from the fibers when the fibers are heated to these elevated temperatures. The lubricant when ;
applied to fibers tenaciously clings to such fibers, thereby reducing the amount of this lubricant required per linear foot of fiber processed and the clean up time for the machinery handling the fiber. When applied to rayon the lubricant enhances the speed of carding of the rayon and at the sam time reduces its fly on drawing and in slubber or roving formation. ;~

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, ";-, The compound has the formula:

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R-C-O(M)H ; .
wherein R is an alkyl radical having from 7 to 21 carbon atoms and ~ is a random mixture of oxyethylene and oxy-propylene groups, wherein the sai~d mixture of oxyethylene and oxypropylene groups is from 65% to B2% of the total ~ ~ :
weight of the compound and wherein the weight ratio of : ~.
oxyethylene to oxypropylene is from 1.0:1 to 7.5:1~
Preferably the O is derived from coconut oil or hydro-.. ~, .
R-C-O
- genated tallow or mixture thereof and the compound is liquid at 2GC with a molecular weight of between ahout 412 and about 1900.

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The lubricated textile fi~er comprises a synthetic fiber and random polyoxyethylene polyoxypropylene glycol :`
monoester on the fiber, the monoester having the formula of the above compound.
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Other objects, features and advantages of the ~ ~
,: , present invention will become apparent from the following ^ ~;~
detailed descrip-tion of the invention.
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DETAILED DESCRIPTION

In more detail, the objects of the present :~
invention are achieved by the hereinafter describ~d water-soluble, liquid, biodegradeable lubricants which have superior lubrication properties for textile fibers, these lubricants being prepared from aliphatic fatty acids, ethylene oxide and propylene oxide. These lubricants are produced by the reaction of a fatty acid or acids having from 8 to 22 carbons, preferably from 12 to 18 car~ons in the alipha~ic chain, wi~h a mixture of ethylene oxide and propylene oxide in a `
~: weight ratio of ethylene oxide to propylene oxide of from about 1.0:1 to about 7.5~ he lubricants of this invention .
comprise the composition obtained by reacting, on a weight basis, 40% to 75% ethylene oxide, 10% to 40~ propylene oxide . and 18% to 35% fatty acid. The resulting random copolymers of polyoxyethylene polyoxypropylene glycol monoester are represented by the following empirical formula~
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`-- 20 wherein R is an aliphatic chain having 7 to 21 carbon atoms and M is a random mixture of oxyethylene [-CH2CH20-] and . ~.
oxypropylene ~-CH2CH(CH3)O-~ groups, said mixture being from about 65% to about 82~ of the total weight of the lubricant, the weight ratio of the oxyethylene to the ::.
: oxypropylene groups of said mixture being in the range of : from 1.0:1 to 7.5~

1 0- ' ~,-1~510~9 The re~ulting random polyoxyethylene polyoxy-propylene glycol monoester has a molecular weight of from about 412 to about l900, a viscosity o from about 50 Centi-poise to about 300 Centipoise at 25C, is water soluble, creating an aqueous solution Up to about 20% by weight in water, at 25C, has a flash point above 4000F and a freezing point or range below 68 F (20 C). -It is to be understood that, if a mixture of aliphatic or fatty acids is used in the condensation reaction, the product obtained will be a mix~ure of compounds having the foregoing formula, but differing from each o~her in the number of carbon atoms in the alkyl group. I have discovered that, only by empolying critical amounts of acid, ethylene oxide and propylene oxide can products be prepared which are water soluble, liquid, biodegradable, and possess ;`
superior lubrication properties for textile fibers.

Aliphatic or fatty acids which are employed in the preparation of my-lubricants are those aliphatic acids ; which contain from 8 to 22 carbon atoms in the aliphatic chain. Mixtures of these acids may also be used, and are `~ `
preferred since their use provides a good balance of proper- `
ties and since these mixtures are readily available from natural, animal and vegetable sources. Aliphatic acids ;~
with l~!SS than 8 carbon atoms give products having poor lubrication properties (presumably because there is insùffi ` ` , :~' ~
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cient repetition of CH2 groups common to mineral oil and vegetable oil lubricants). Aliphatic acids with greater than 22 carbon atoms result in products of such high mole-cular weight that they are highly viscous and would have value as lubricants only under very high temperature con-ditions, which are not encountered in textile processing~
Examples of acids which are operable in the present process include caprylic, pelargonic, capric, lauric, myristic, palmitic, stearic, oleic, linoleic, hydrogenated marine oil fatty acids r isotearic and mixtures thereof.
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` The products of this invention are prepared by condensing the fatty acid or mixture of acids, as described above, with a mixture of ethylene oxide and propylene oxide.
The oxide mixture is preferably added in a single continuous step or in a series of steps to the acid. If added in a series of steps, the oxide ratio in each step need not be in the range, as described, but the total weights after all steps are completed must be in the ratio specified and in the total fraction of the product, as defined.
' The ratio of oxides is critical to the properties of the resulting reactlon products. If the ethylene oxide:propylene oxide ratio is less than about 1.0:1, the ~
finished product will not be water soluble. If this ratio ~`
is greater than about 7.5:1, the finished products (especially ; -from the higher moleaular weight fatty acids) will be viscous fluids or pastes.

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, Furthermore, khe weight percent of oxide mixture in the finished product is critical. If the oxide mixture is less than about 65% of the product, then the product will ;~
not be water soluhle to any appreciable extent~ If the oxide mixture is greater than a~out 82~ of the product, then the viscosity of the product will he too high, at ambient temperature, for lubricating of textile fibers if such fiber is to be processed at high speed~

The pxoducts of this invention are yenerally ~;
prepared by condensation of the fatty acid or acids with a mixture of ethylene oxide and propylene oxide in the presence of an alkaline catalyst, at temperatures from about 110C
to about 180C and under pressures from ambient pressure up to about 100 psi.

A better understanding of the present invention `~
will be had by reference to the following examples. All parts specified in the examples are by weight. ~
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The procedure set forth below was repeated for each group of chemicals specified in Table I.

A clean, dry reactor was purged with nitrogen and ; charged with an aliphatic acid and potassium hydroxide catalyst (1.0-1.5% by weight of the acid)D This mixture :
, wa~ stirred at 135C-150C while a mixture of the ethylene oxide and prop~lene oxide was added to the acid catalyst ;
mixture, over a period of from 4 to 8 hours, at pressures of from 20-100 psi. After about one additional hour, the pressure was stabilized indicating reaction of the oxides ~;
was complete. The product was cooled below 100C, the reactor was vented, the catalyst was neutralized with glacial acetic acid, and the reaction product, discharged.

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In Table I, it i5 noted khat Examples V, ~I, YII, XIV, XV and XVI result in unsuitable products. In Example V the proportion of acid was too high, resulting in a water insoluble liquid, In Examples VI and XIV the amount of ;
propylene oxide was too low, resultin~ in a paste. In ;
Examples ~II and XV the amount of propylene oxide was too high resulting in an insoluble li~uid~ In Example XVI the amount of ethylene oxide was too high resultirlg in a paste~

Selected products from the above examples were further tested for compatability with commonly used anti- `;
static agents, using seven parts lubricant and one anti-static agent. Table II below gives the results of the tasts.

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rrABLE II
COMPATABILITY
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Example No. Example Number Antistatic Properties of Test Lubricant From Agent of the Table I Mixture __ .. . _ _ . __ _ XVIII Ex. III Atlas Clear, ;~
. G-263( ) Completely :
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XIX Ex. X NopcostatTM Clear, : -:
~92(2) Completely ; ::
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Ex. XII GAFAC Clear, MC-470~ ) Completely ~:
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. G-3780A( ~CIoOpletely ; :

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(l) N-Cetyl-N-ethyl morpholinium ethosulfate

(2) Fatty aaid imidazoline

(3) Complex organic phosphate ester ~.
:~ (4) Polyoxyethylene amine condensate .
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To compare the thermal stability of the lubricant , : `
of Exa~ple III ~ith other similar fiber finishes, beakers contai ing equal quantities of each ~ere placed side-by-side on a hot plate, and the temperature was allowed to rise, rapldly. Careful note was made of the obvious manifestations of decomposition.
The results of these experiments are contained in Table III.

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TABLE III ~ -THEl~AL STABILITY
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PRODUCT TIME (min) TEMP. C. COLOR REMARKS
. _ _ -Nopcostat 0 25 Ambex Appearance 2152-P ~ . Prior to . Heating ..
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Atlas 0 25 Amber Appearance G3780-A Prior to :~ :
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Example III O 25 Straw Appearance .
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. _ _ . _ , 2152-P 40 160 Dk. Red Smoking .
G3780-A 40 160 Red Smoking ; Example III 40 160 Straw Light Smoke :i . _ `~ 2152-P 80 180 Purp-Black Heavy Smoke .
:~ G3780-A 80 180 Purp-Black Heavy Smoke Example III 80 180 Light Light Smoke Yellow . :.
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In order to test the steam volitality of Example III
and compare it with similar products, the same were dissol~-ed or dispersed to provide about 0.3% concentration in 150 ml.
o-f tap water. The water was then evaporated at 85C-95C. in an oven in order to simulate conditions in a drying chamber for wet staple ~ibers. By keeping the temperature below 100C., the loss of product was assumed to be a function of volatility with water vapor since there was no boiling or entrainment effect.l ~ `
The results of these tests are contained in Table IV. ~i , ,, - , :
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TABLE IV :`
STEAI~l VOLATILITY

INITIAL FINAL RESI~UE FRO~I
PRODUCT WEIGHl' - g. ~YEIGHT - g. H20, g~ ~ LOSS ~ ~
_, _ . _ _ ._ __ ''~ ., NOPCO . 0.4755 0.3942 0,0074 18.7% .
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Example III 0.4482 0.449S 0.0074 1.3% ;i: 1 0 _ . . . _ _ ' .:

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Still allother test was conducted using the lubricants of Examples III and IX l~hich ~ere respectively applied to acrylic spun carpet yarn and pulled by a weight over a steel pin. An acceptable lubricant under such circumstances would generate less than 220 grams of tension ~nd a prior art acceptable mineral oil type of lubricant generated 195 grams. Yarns treated with~ -~; Example III developed 145 grams o~ tension and yarn treated with Example IX developed 140 grams.

In using my lubricant, from ahout .2% to about 3% lubri^ ;~
cant based on the weight of the fibers is required. ~ith spun ` yarns for apparel, my lubricant should comprise about .25% o~
the total weight o the yarn. With the heavier carpet yarn, it should constitute about .6% of the total weight of the yarn.
In filament yarn for knitting, it should constitute about 1%, ~ `
of the total weight of the yarn and with industrial~yarns~ such ~j ~ as tire cord~ cord ~or conveyor belts and the like, it should `
`~ consti~ute from about 2~ to about 3% of the total weight o-f the cord or yarn. ' i~
i One advantage o-f the present lubricant is the fact that it needs no emulsifier to produce a suitable lubricant.
In other words, the random copolymers of polyoxyethylene polyoxy- ~
propylene glycol monoester of the present invention are suitable ~ ;
for use, as such, or in aqueous solution and can be applied to both monofilament fibers and-spun or staple synthetic fibers ~; 25 in the same manner as the prior art inishes are applied. For example, my lubricant can ' :

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~ 9 be dribbled on~o the fiber mat. The fibers may be dipped into , -the lubricant and thereafter squeezed or the lubricant may be sprayed onto the fibers.

Furthermore, my lubricant can be mixed with a variety 5 of antistatic agents, when desired. Thus, when used as a lubri- ~
cant for nylon or polyester fibers, it is recommended that my ~; -lubricant be used in conjunction with one of the antistatic agents with which the lubricant is compatible.

My lubricants are particularly useful for lubricating nylon and polyester texturized filament and for rayon staple fiber.
Also, when minute amounts of my lubricants are to be applied to .- i - ~ ., ~: jstaple fibers, the lubricant is diluted ~Yith water to provide up to about 20%, by weight, an aqueous solution of my lubricant. This , ; is then sprayed onto the staple fiber mat. About a 10% aqueous ,' solution is recommended. After spraying, the water is usually driven of~ using hot air.
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As a rule, my lubricants are applied to synthetic staple yarns immediately after the yarn is cut and prior to the time that the yarns are baled. With :.m~no~ilament yarns, my lubricants should~ be applied, immediately after the;~iber is drawn, as by "~iss coating" or by passing the drawn fiber throu~h a bath of my lubricant.

Whlle my lubricants are particularly suitable for ;~

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l~S~O~9 application to substantially all synthetic fibers, my lubricant is also useful for application to natural f.ihers, such as cotton, wool and silk.

From the foregoing description, it should now be j ~:
apparent that my lubricants, being chemically prepared, have a : uniformity which exceeds those natural lubricants of the prior art.
Thus, the problems of quality control are reduced. Variation in I ~
the pick up and hand of fibers treated with my lubricant are i ~1 minimum and increases in carding speed is possible when synthetic fibers containing my lubricant are processed.

Furthermore, the lubricant itself requires no special handling i~ that no external heat, steam tracer lines, or speci.al `;~
storage vats are required to store lubricants o the present ! ~ ;
. invention, since they are:liquid under ambient conditions. Lubri~
~: 15 cants of~the present invention also do not separate during bulk . ; .
: ;storage of the same. Other prior art finishes do tend to separate - `1.;
when stored for extended periods of time.

The lubricants of the present i.nvention appear to I ~ I
be stable at temperatures much higher than those temperatures .~ .
which would be applied to fibers during the drying processes.
Furthermore, the lubricants of the present invention do not appear to readily be distilled by steam. This appears to be a major advance, for example, for rayon treated with my lubricants o~er , , . .~
rayon treated with prior art lubricants which readily distill ~ .
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,.._ ~ ~5 ~ O ~ g off of the rayon during the oven drying o the product, and thereby collect in the exhaust systems, causing severe fire hazards.

Indeed, the lubricants of the present invelition appear .
to remain on the fibe~s even after steam drying~ thereby reducing ~ ~
the fire hazard,and reducing the clean up time. . :;-While~ heretofore~ the machinery utilized in the produc~
tion of staple fibers became extremely dirty, due to ~he loss of lubricant during the processing of the staple, the present lubricants appear to have just the opposite effec~. For example, when a lubricant of the present invention WclS employed on rayon fibers 9 it cleaned up. the machinery through which the fibers passed, instead of causing an accumulation of ~'gunk" on such i~ ~ machinéry.`- `
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. effe:cted by the normal pH changes in the finish water. Indeed, ` . when some prior art lubricants ax.e used, hand can be completely changed with a wash pH change.

. ` , Of major economic importance when using the lubricants ~ `
: 20 of the present invention with rayon staple fibers, is the fact that smaller amounts of heat are required to dry the;fibers which contains the lubricants of the present invention than rayon which has been treated with prior art lubricants. Thus, ' `
, .. -; .: -, , .: , ,. ~. - ., ~. . . -a mill can use its e~isting equipment for drying and by simply , adding additional spinnerettes can eed more .Fiber poundage through this drying equipment, thereby increasing capaci~y by some 15%-25%.

The lubricants of the present invention, being es~ers~
'i!~have a mild pleasant smell and, therefore, imparts this smell to the mill during use. Purthermore, the bales of ibers treated with the present lubricants appear to have a clean smell.

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; ,i The evenness and uniformity of application of the present lubricants to the fibers appears to be improved over prior ar~ ¦
lubricants. When fibers, treated wi~h lubricants of the present nvention are used, the f]nish solution in the mill remains clear , and will remain stable without agitation.
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The ~extile cards are~able to run a~ a higher pounds per hour rate when staple fibers using the present lubricants I ;~
" are processed in these cards.
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of synthetic fibers treated with my lubricarlts appears to I
be less.

The wet-out rate of fibers treated with my lubricants appears to be much faster than fibers treated with prior art ;lubricants which are water insoluble. This is especially helpful ., ~ on non-woven fabrics, such as innerliners for disposable diapers.
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Tlle Tesiliency, openness an~ hand oE staple fibers ~hich utilize my lubricants appear to be excellent. ~ith ~he addition;' of the good hand l~hich is imparted by the lubricants of the presént invention, a mill should have a high rate of confidence in the ,~fiber finished wi~h the lubricants of the present invention.
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' The card web, roving package and yarn has a leaner and cleaner appearance.
!
The tackiness which is common in card laps fro~ fibers treated with fatty acids, is eliminated when fibers treated with ! -~10 lubrican~s of the present invention are processed.

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Claims (13)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A compound having the formula:

R-?-O(M)H
wherein R is an alkyl radical having from 7 to 21 carbon atoms and M is a random mixture of oxyethylene and oxypropylene groups, wherein the said mixture of oxyethylene and oxypropylene groups is from 65% to 82% of the total weight of the compound and wherein the weight ratio of oxyethylene to oxypropylene is from 1.0:1 to 7.5:1.

2. The compound defined in Claim 1 wherein the R-?-O
is derived from coconut oil.

3. The compound defined in Claim 1 wherein the R-?-O

is derived from hydrogenated tallow.

4. The compound defined in Claim 1, said compound being liquid at 20°C and having a molecular weight of between about 412 and about 1900.

5. Process of preparing a liquid, water soluble, biodegradable, textile fiber lubricant comprising, condensing from approximately 40% to approximately 75%, by weight, ethylene oxide, from approximately 10% to approximately 40% by weight propylene oxide and from about 18% to about 35%, by weight, a fatty acid having from about 8 to about 22 carbons, said ethylene oxide being in proportion to said propylene oxide by weight from about 1.0:1 to about 7.5:1, in the presence of an alkaline catalyst.

6. The process defined in Claim S including heating the condensation reactants to a temperature of between about 110°C and about 180°C at pressures up to about 100 psi for from about 4 to about 8 hours.

7. The process defined in Claim 6 wherein said fatty acid is derived from coconut oil.

8. The process defined in Claim 6 wherein said fatty acid is derived from hydrogenated tallow.

9. The process defined in Claim 6 wherein said fatty acid is a mixture of fatty acids.

10. A lubricated textile fiber comprising:

(a) a synthetic fiber, and (b) random polyoxyethylene polyoxypropylene glycol monoester on said synthetic fiber, wherein the random polyoxyethylene polyoxypropylene glycol monoester has the formula R-?-O(M)H
wherein R is an alkyl radical having from 7 to 21 carbon atoms and M is a random mixture of oxyethylene and oxypropylene, the said mixture being from about 65% to about 82% of the total weight of the lubricant and the weight ratio of oxyethylene to oxypropylene in said mixture being in the range of from 1.0:1 to 7.5:1.

11. The lubricated textile fiber defined in claim 10 wherein said random polyoxyethylene polyoxypropylene glycol monoester is in its liquid phase and is biodegradable.

12. The lubricated textile fiber defined in claim 10 wherein said random polyoxyethylene polyoxypropylene glycol monoester constitutes from about .2% to about 3% by weight of said synthetic fiber.

13. A lubricated textile fiber as claimed in claim 10 wherein said monoester mixture is liquid at 20°C., said compounds have molecular weights between about 412 and about 1900 and the R-?-O(M)H

is a mixture of fatty acids derived from the group consisting of coconut oil and hydrogenated tallow.