Note: Descriptions are shown in the official language in which they were submitted.
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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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.~ 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.
..
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.
;
To overcome this, the lubricant is emulsified with the
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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.
, . :
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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either because they are water insoluble o~ tq~ viscous o~
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-
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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 ~ ~
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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~
. O '`,`'~
`~ R-C -O-(M)H ~ :
`-- 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~
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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.
':
` 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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. XXI Ex. XVII ArrLAS 4) Clear, ~-:
. 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 .
. Heati.ng ~:
. _ _ . _ ,
2152-P 40 160 Dk. Red Smoking .
G3780-A 40 160 Red Smoking
; Example III 40 160 Straw Light Smoke
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`~ 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% .
RSF-15 . :
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
- 22 -
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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.
, !
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 ;~
- 23 -
; .
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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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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:
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~ The lubricants of the present invention are not
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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,
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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.
: , ' `
; ,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.
,, 11 , , .................................................... , .
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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Il The 1y on drawing and especially on roving frames
!.
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.
;` - 26 -
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0~9 ! ;:
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.
, ~ "
' 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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