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US2742379A - Treatment of textile fibers with antistatic agent and product thereof - Google Patents

Treatment of textile fibers with antistatic agent and product thereof Download PDF

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Publication number
US2742379A
US2742379A US412661A US41266154A US2742379A US 2742379 A US2742379 A US 2742379A US 412661 A US412661 A US 412661A US 41266154 A US41266154 A US 41266154A US 2742379 A US2742379 A US 2742379A
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Prior art keywords
antistatic agent
hydrophobic
mixture
product
treatment
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US412661A
Inventor
Schofield Frank Mcgrew
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EIDP Inc
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EI Du Pont de Nemours and Co
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/68—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof
    • D06M11/72—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof with metaphosphoric acids or their salts; with polyphosphoric acids or their salts; with perphosphoric acids or their salts
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00—Chemistry of carbon compounds
    • Y10S260/15—Antistatic agents not otherwise provided for
    • Y10S260/16—Antistatic agents containing a metal, silicon, boron or phosphorus
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2967—Synthetic resin or polymer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2967—Synthetic resin or polymer
    • Y10T428/2969—Polyamide, polyimide or polyester
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2971—Impregnation

Definitions

  • I-Iydrophobietextile fibers tendto accumulate electrostatic charges due to. their poor, electrical conductivity.
  • 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
  • phosphate esters result from thereaction ofil moles of,alcohol ormixture ofalcohols, with one mole of phosphoric :anhydride. In thejcor'nposition obtained,-
  • 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.
  • 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.
  • 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.
  • a still further object is to provide a process for impregnating a hydrophobic non-cellulosic. textile fiber,
  • amine portion is an alkanol amine, more specifically diethanol amine.
  • alkanol amine more specifically diethanol amine.
  • alkyl esters of pentavalent phosphorus acids or acid anhydrides may be represented by' the following' general formula:
  • 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.
  • 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 discussed is usually nil.
  • 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
  • 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.
  • alkyl esters being characterized by the presenceofl -P -0 -P linkages and wherein-the alkyl radical con-f tains at least 8 carbon atoms.
  • 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 latterbeing a 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.
  • 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.
  • an antistatic agent a mixture of di-ethanolamine selected from the group, consisting of hydrogen atoms salts of phosphate esters which

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

' 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;be.li'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):
Product:
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

Claims (1)

1. HYDROPHOBIC, NON-CELLULOSIC TEXTILE 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 PHOSPHROUS ACIDS AND PENTAVALENT PHOSPHOROUS ACID AHYDRIDES, SAID ALKYL ESTERS BEING CHARACTERIZED BY THE PRESENCE OF -P-O-P-LINKAGES AND WHEREIN THE ALKYL RADICAL CONTAINS AT LEAST 8 CARBONS ATOMS
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2837446A (en) * 1951-08-31 1958-06-03 Monsanto Chemicals Textile materials with an anti-static finish and process of making same
US2934682A (en) * 1956-07-05 1960-04-26 Sprague Electric Co Electrolytes
DE1091078B (en) * 1958-12-13 1960-10-20 Glanzstoff Ag Process for treating synthetic threads, fibers, etc. to reduce their tendency to become electrostatically charged
DE1096322B (en) * 1959-01-07 1961-01-05 Glanzstoff Ag Process for the antistatic finishing of polyamide fibers or threads
US2990604A (en) * 1956-07-18 1961-07-04 Ici Ltd Process of thermally treating and lubricating polyethylene terephthalate filaments and yarns
DE1167787B (en) * 1960-02-16 1964-04-16 Bayer Ag Process for the anti-static treatment of textile materials
US3150039A (en) * 1960-11-16 1964-09-22 Union Carbide Corp Insecticidal method using both pyrophosphoric and polyphosphoric acid partial ester ammonium salts and process for preparing same
US3634117A (en) * 1968-02-17 1972-01-11 Glanzstoff Ag A textile material coated with an ammonium dialkyl phosphate antistatic agent
US3770495A (en) * 1968-01-08 1973-11-06 H Lenz Non-adhesive high elastic elastomer threads
US3852288A (en) * 1970-08-27 1974-12-03 Du Pont Process for color stable alkyl and alkenyl acid phosphate compositions
US4072617A (en) * 1976-04-12 1978-02-07 Dow Badische Company Finish for acrylic fiber
FR2399433A1 (en) * 1977-08-01 1979-03-02 Ciba Geigy Ag QUATERNARY AMMONIUM SALTS OF ANTISTATIC PRODUCTS OR TOUCH SOFTENING AGENTS WITH FATTY ACID REMAINS, THEIR PREPARATION PROCESS AND THEIR USE
US4213867A (en) * 1978-12-29 1980-07-22 Domtar Inc. Fabric conditioning compositions
US4292182A (en) * 1978-10-30 1981-09-29 Badische Corporation Imparting anti-soiling properties to fibers
US4296165A (en) * 1978-04-24 1981-10-20 The Diversey Corporation Antistatic natural and synthetic textile materials which have been treated with salts of orthophosphoric or polyphosphoric acid

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676122A (en) * 1951-01-09 1954-04-20 Du Pont Antistatic treatment of hydrophobic fiber
US2676975A (en) * 1950-08-31 1954-04-27 Celanese Corp Process for production of phosphate esters
US2676924A (en) * 1952-06-04 1954-04-27 Celanese Corp Textile lubricant

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676975A (en) * 1950-08-31 1954-04-27 Celanese Corp Process for production of phosphate esters
US2676122A (en) * 1951-01-09 1954-04-20 Du Pont Antistatic treatment of hydrophobic fiber
US2676924A (en) * 1952-06-04 1954-04-27 Celanese Corp Textile lubricant

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2837446A (en) * 1951-08-31 1958-06-03 Monsanto Chemicals Textile materials with an anti-static finish and process of making same
US2934682A (en) * 1956-07-05 1960-04-26 Sprague Electric Co Electrolytes
US2990604A (en) * 1956-07-18 1961-07-04 Ici Ltd Process of thermally treating and lubricating polyethylene terephthalate filaments and yarns
DE1091078B (en) * 1958-12-13 1960-10-20 Glanzstoff Ag Process for treating synthetic threads, fibers, etc. to reduce their tendency to become electrostatically charged
DE1096322B (en) * 1959-01-07 1961-01-05 Glanzstoff Ag Process for the antistatic finishing of polyamide fibers or threads
DE1167787B (en) * 1960-02-16 1964-04-16 Bayer Ag Process for the anti-static treatment of textile materials
US3150039A (en) * 1960-11-16 1964-09-22 Union Carbide Corp Insecticidal method using both pyrophosphoric and polyphosphoric acid partial ester ammonium salts and process for preparing same
US3770495A (en) * 1968-01-08 1973-11-06 H Lenz Non-adhesive high elastic elastomer threads
US3634117A (en) * 1968-02-17 1972-01-11 Glanzstoff Ag A textile material coated with an ammonium dialkyl phosphate antistatic agent
US3852288A (en) * 1970-08-27 1974-12-03 Du Pont Process for color stable alkyl and alkenyl acid phosphate compositions
US4072617A (en) * 1976-04-12 1978-02-07 Dow Badische Company Finish for acrylic fiber
FR2399433A1 (en) * 1977-08-01 1979-03-02 Ciba Geigy Ag QUATERNARY AMMONIUM SALTS OF ANTISTATIC PRODUCTS OR TOUCH SOFTENING AGENTS WITH FATTY ACID REMAINS, THEIR PREPARATION PROCESS AND THEIR USE
US4264516A (en) * 1977-08-01 1981-04-28 Ciba-Geigy Corporation Quaternary ammonium salts of antistatic agents or softening agents containing fatty acid radicals, process for the production and use thereof
US4296165A (en) * 1978-04-24 1981-10-20 The Diversey Corporation Antistatic natural and synthetic textile materials which have been treated with salts of orthophosphoric or polyphosphoric acid
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