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Publication numberUS2742379 A
Publication typeGrant
Publication dateApr 17, 1956
Filing dateFeb 25, 1954
Priority dateFeb 25, 1954
Publication numberUS 2742379 A, US 2742379A, US-A-2742379, US2742379 A, US2742379A
InventorsSchofield Frank Mcgrew
Original AssigneeDu Pont
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Treatment of textile fibers with antistatic agent and product thereof
US 2742379 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

' fibers in the mill.

a ,Batented Apn-vlj, 1 956 "TREATMENT or TEXTILEFlBERS wiTHANTrsrATrc NT Dr onUcr 'rrnznnor Franlr McGrew schofie ldgwoodstown, N. 3., assignorto "LIdu Pont de Nemoursand -Company, Wilmington,

e nven swim No Drawing. ApplicationFebruary 25,1954,

. Serial No. 412,661 a p --6 enam l-51c]; t/#1333) invention relates i to hydrophobic, non-cellulosic textile materials having improved. qualities and morepartic arty to: hydrophobic, .non-cellulosic fibers, filaments,

x tile material having improved I in?"taticproperties and tofa process ,of imparting these antistatic properties to the textile material. V

I-Iydrophobietextile fibers tendto accumulate electrostatic charges due to. their poor, electrical conductivity.

' This accumulation of electrostatic chargesgenerally occursjltltiring the worlging of ithe fibers in the textile m ills', where through repeated friction of the fibers, filaments or yarns with one another and with the equipment, these electrostatic charges accumulate and seriously interferewith the spinning, drawing, twisting, weaving and knitting operations. These charges can also be wheren isia small whole number of troml to 6 and R is selected from the groupconsisting of hydrogen atoms and normal alkyl radicals of, from 8 to 18 carbon atoms and ,wherein on the average one half of the Rs of themixture are normal alkyl radicals and the other half are hydrogenatomsg These phosphate esters result from thereaction ofil moles of,alcohol ormixture ofalcohols, with one mole of phosphoric :anhydride. In thejcor'nposition obtained,-

about 75, to 100 ;wt. percent of the phosphorus; is connected through an oxygen linkage to another phosphorus atom, as shown-by titrationwith' a standardalkali solu tion both. beforerandjafter, hydrolysis witht water. It

is believed that the greater portion,of .thecompositiont is in the pyrophosphate form, although up to of the compositionmay be in the form of orthophospha'testi he-$.91 q t i q -ere ssausnfl d slfmd sth arrrinein order to produce the {desired salt.

annoying and troublesomewhen fabrics made from these hydrophobic textile fibers are in service in the form of carpets, drapes, clothing and automobile seat covers.

, Although the, general ideaof treating textile fibers with agent-is by jno.-means a simple one.

bricants,*sizes and other. agents commonly applied to It must allowgproper running tensions of filament during drawing andgtwisting operations. It must be non-corrosive to theappa'r'atus in which. the fiber will be worked; and it .mustbenon-toxic and have no the ultimate wearer.

These compositions arereadily soluble in alcohol and are soluble or self -dispersible in water. Consequently, they can be applied to fibers from either medium with the most common and preferred method of application-being padding from a dilute aqueous solution or dispersion.

They can also-be applied byvspraying or from rollers which are in contact with the fibersjat ionepoint and the treat- *ing.bath at another. 5, r

, The following examples willabetter illustrate thenature of thepresentwinvention; however, the invention isinot intended to;'mited to theseeexamplesp Parts turewhose composition is-approximately 3% n-decanol,

61% .n-dodecanol 23% r -tetradecanol, 1l% hexadecanol and 2% octadecanol, there was added 142 parts of phosphorieanhydride at a rate such that the tempera;

tiire of the well-agitated charge was maintained at 7S"- 80 1C, while, the "reactor jacket temperature \')va's. held 1 between g40 and 7O 'C."' The reactionnias' was then cellulosic textile fiber v impregnated with an antistatic;

agent. A still further object is to provide a process for impregnating a hydrophobic non-cellulosic. textile fiber,

withvan antistatic agent as defined below, to improve the electrostatic, qualities. Other objects will appear here-.

be defined broadly as amine salts of mixturesof alkyl esters of pentavalent phosphorus acids or acid anhydrides,

wherein the amine portion is an alkanol amine, more specifically diethanol amine. These mixtures of alkyl esters of pentavalent phosphorus acids or acid anhydrides may be represented by' the following' general formula:

phosphorous oxygen-phosphorus bonds. 7 ,v The main body of the intermediate was} added with stirred 'tor twelve hoursat C. Theacidiniimber of the productat this point was 227 and 23 mole, ;percent of the total tit atabl'e acidic constituents was shown by potentiometric titration, to bejdibasic. [A srnall 'samplei p y; of this intermediate was reacted with watenfor iseveral injurious dermatological effects upon the worker or upon hours at about 8'0 C. and the acid number rose'to 355 and the mole percent of the total titratable acidicjcon stituents titratin'g as dibasic rose to 81.6, showingv the presence, in the above described'intermediate priorto reaction with water, of a'high proportion of unreacted agitation at temperatures not exceeding 80? (3-..tof4 5.

parts of diethariolamine, giving a viscous paste. flheIpH, of a 10%,aq'ueous dispersionpf this paste was 7.45.

i 1 Example 11 of diethanolamirie to give pH 7.0-7.5 as a 10%"aqueousi solution, was soluble in water.

The evaluation of the antistatic quality of the treatc d In a manner similarto that described in Example I, a product was made in which the higher alcohol used was @260, arts of n-octanol. fIhisaproduct, after-neutralize tion with anamount of diethanolamine to give: pH 7.0-7.5. of a 10% aqueous solution, was soluble in water. a,

fiber'particula'rly when in fabric form was carried out essentially as follows:

A small piece of hydrophobic fabric (approximately cm. 3 cm.) is immersed for 30 sec. in approximately 100 cc; of'an-aqpeoussol-ution or a 95%- ethanol solutionor the antistatic agent'containing'a'knownamount of' the agent. The fabric 'is removed,"-a-ir-dried, and weighed again to provide a 'ba-sis'for -calculating the-pick-up of ant-i-staticagent. i r

The electrical resistance of the strip is measured-at a controlled relative humidity of 25% on a special apparatns which comprises two electrodes separated by a space of 1. 25 cmjandhaving a potential difference of 90 volts. The fabric is held in place between the electrodes so as to provide a conducting area 1.25 cm. long and Resistance: 1: A ti-static rating The rating of the untreated control in the noncellulosic,

hydrophobic fibers herein discussedis usually nil.

Each agent whose preparation is described in Examples 1 to 3 'was applied separately to tafetta fabrics of nylon, Orion acrylic fiber and Dacron-polyester fiber by padding from. a dilute aqueous solution or dispersion. This was done by padding for approximately 30 seconds in 250 parts by weight of water containing 1 part by weight of the antistatic agent. Afterw ringing and air drying toactive-ingredient loadings of about-0.5% dry weight based on theweights of the fabrics, the following results were obtained (electrical resistance of the treated fabrics was measured by the above described method):


g Anti-staticrating l Y Excellent Ex. II .'Excellent III;" Excellent With active ingredient loadings of about 0.1% based on the weights of the fabrics, the following results were obtainedtelectrical resistance of the treated' fabrics was measured by thev above described meliod):

Product; Anti-static rating Ex. I Very good Ex. II' Very good Ex;III Y Very good and economical. a

w The preferred phosphateesters of the present inven tion are thoseinwhich the normal alkyl radical of the ester groups contain 12 and 14- carbon atoms. Also preferred are those made from commercial mixtures of these C12 and C14 alcohols which are marketed as technical lauryl alcohol. A specific mixture available on the. market is described in Example I. Y

Astor the chemical uaturewof the fiber to be treated, this. invention is operable on. anything which has. a tend: 1 ericy to accumulate an electrostatic charge- The. preferredmaterials. the textilefiber s. field. are polyamides V (e. g., nylon), polyesters (e. g., polyethylene terephthalate)- and pol-yacry-lics (e. g-., polyacrylonitrile}; These can be in the form of fibers, filaments, yarn or fabrics. The present invention is particularly useful in the automobile seat cover trade, since these seat covers are often made of nylon and other hydrophobic materials and they have a great tendency to accumulate an electrostatic charge.

As many "apparentlywidely different embodiments of this invention may be made without departingfrom the spirit andscope thereof,'it is to. be understood that this invention is not limited to the" specific embodiments thereof except as defined in the appendedclaims.

l. Hydrophobic, non-cellulosictextile; fiber having incorporated therein about 0.02 to 2.5% by weight of an antistatic agent, the latter'being a mixture of alkanol amine salts of alkyl esters of phosphorus; compounds selected from the group consisting of pentavalent phos! phorus acids and pentavalent'pho'sphorus acid anhydrides,

said alkyl esters being characterized by the presenceofl -P -0 -P linkages and wherein-the alkyl radical con-f tains at least 8 carbon atoms.

2. Hydrophobic, non-cellulosic textile fiber having incorporated therein from, about 0.02 to 2.5% by. weight of an'antistatic agent, thelatter'being a mixture of diethanolamine .salts' of phosphate esters of the general formula wherein n is a small whole number of from 1 to 6 and incorporatedtherein' from Oil to 1% by weight of an antistatic agent, the latterbeinga mixture of di-ethanolamine salts of phosphate esters of the general formula where 'n is a small whole number from 1 to 6 and R is selected from the group consisting of hydrogen atoms and normal, aliphatic hydrocarbon radicals of from 12 to 14 carbonatoms and wherein on the average one half of the Rsinthe mixture are hydrogen atoms.

4 Hydrophobic, non-cellulosic textile fiber having incorporated therein'from 0.1 to 1% by weight of an antistatic agent, the latter being a mixture of di-ethanolamine selected from the group, consisting of hydrogen atoms salts of phosphate esters which are produced by the reacv tion of phosphoric anhydride with an alcohol mixture comprising approximately 3% n-decanolg 61% n-dodecanol, 23% n-tetradecanol, 11% hexadecanol and 2% octadecanol, saidphosphate esters having the following general formula RO n-l OR wherein n is a small whole number from 1 to 6 and R is and normal aliphatic hydrocarbon radicals of from 10 to 18 carbon atoms and wherein on the average one-half of the Rs in the mixture are hydrogen atoms.

5. Process of improving the electrostatic qualities of hydrophobic, non-cellulosic textile fiber which comprises impregnating the same with a mixture of alkanol amine salts of phosphate esters of the general formula wherein n is a small whole number of from 1 to 6 and R is selected from the group consisting of hydrogen atoms and normal, aliphatic hydrocarbon radicals of from 8 to 18 carbon atoms and wherein on the average one-half of the Rs in the mixture are hydrogen atoms,

6. Process of improving the electrostatic qualities of hydrophobic, non-cellulosic textile fiber which comprises impregnating the same by padding from a dilute aqueous dispersion with a mixture of diethanolamine salts of phosphate esters of the general formula P O --P O P R--0 8 11-1 OR References Cited in the file of this patent UNITED STATES PATENTS 2,676,122 McCarthy Apr. 20, 1954 2,676,924 Fortess et a1. Apr. 27, 1954 2,676,975 Fortess et a1 Apr. 27, 1954

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2676122 *Jan 9, 1951Apr 20, 1954Du PontAntistatic treatment of hydrophobic fiber
US2676924 *Jun 4, 1952Apr 27, 1954Celanese CorpTextile lubricant
US2676975 *Aug 31, 1950Apr 27, 1954Celanese CorpProcess for production of phosphate esters
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2837446 *Jun 11, 1956Jun 3, 1958Monsanto ChemicalsTextile materials with an anti-static finish and process of making same
US2934682 *Jul 5, 1956Apr 26, 1960Sprague Electric CoElectrolytes
US2990604 *Jul 8, 1957Jul 4, 1961Ici LtdProcess of thermally treating and lubricating polyethylene terephthalate filaments and yarns
US3150039 *Nov 16, 1960Sep 22, 1964Union Carbide CorpInsecticidal method using both pyrophosphoric and polyphosphoric acid partial ester ammonium salts and process for preparing same
US3634117 *Feb 17, 1969Jan 11, 1972Glanzstoff AgA textile material coated with an ammonium dialkyl phosphate antistatic agent
US3770495 *Oct 28, 1971Nov 6, 1973K BernklauNon-adhesive high elastic elastomer threads
US3852288 *Oct 11, 1972Dec 3, 1974Du PontProcess for color stable alkyl and alkenyl acid phosphate compositions
US4072617 *Apr 12, 1976Feb 7, 1978Dow Badische CompanyFinish for acrylic fiber
US4213867 *Dec 29, 1978Jul 22, 1980Domtar Inc.Fabric conditioning compositions
US4264516 *Jul 17, 1978Apr 28, 1981Ciba-Geigy CorporationQuaternary ammonium salts of antistatic agents or softening agents containing fatty acid radicals, process for the production and use thereof
US4292182 *Oct 14, 1980Sep 29, 1981Badische CorporationImparting anti-soiling properties to fibers
US4296165 *Jul 2, 1979Oct 20, 1981The Diversey CorporationAntistatic natural and synthetic textile materials which have been treated with salts of orthophosphoric or polyphosphoric acid
DE1091078B *Dec 13, 1958Oct 20, 1960Glanzstoff AgVerfahren zur Behandlung von synthetischen Faeden, Fasern usw. zur Herabsetzung ihrer Neigung, sich elektrostatisch aufzuladen
DE1096322B *Jan 7, 1959Jan 5, 1961Glanzstoff AgVerfahren zur antistatischen Avivage von Polyamid-Fasern oder -Faeden
DE1167787B *Feb 16, 1960Apr 16, 1964Bayer AgVerfahren zur antielektrostatischen Ausruestung von Textilmaterialien
U.S. Classification428/394, 428/396, 260/DIG.160, 252/8.61, 558/152, 428/395
International ClassificationD06M13/292, D06M11/72
Cooperative ClassificationY10S260/16, D06M13/292, D06M11/72
European ClassificationD06M11/72, D06M13/292