US2842462A - Antistatic synthetic textile material - Google Patents

Antistatic synthetic textile material Download PDF

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US2842462A
US2842462A US47581254A US2842462A US 2842462 A US2842462 A US 2842462A US 47581254 A US47581254 A US 47581254A US 2842462 A US2842462 A US 2842462A
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mols
antistatic
textile material
synthetic textile
fibers
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Haas Hermann
Lietz Gustav
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Bohme Fettchemie GmbH
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Bohme Fettchemie GmbH
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244Treating 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
    • D06M13/282Treating 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
    • D06M13/292Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244Treating 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
    • D06M13/282Treating 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
    • D06M13/285Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02Water
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/18Natural waxes, e.g. ceresin, ozocerite, bees wax, carnauba; Degras
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/021Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
    • C10M2207/404Fatty vegetable or animal oils obtained from genetically modified species
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/10Amides of carbonic or haloformic acids
    • C10M2215/102Ureas; Semicarbazides; Allophanates
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/042Metal salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2240/00Specified uses or applications of lubricating compositions
    • C10N2240/62Textile oils
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40Reduced friction resistance, lubricant properties; Sizing compositions
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00Chemistry of carbon compounds
    • Y10S260/15Antistatic agents not otherwise provided for
    • Y10S260/16Antistatic agents containing a metal, silicon, boron or phosphorus
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2904Staple length fiber
    • Y10T428/2907Staple length fiber with coating or impregnation
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber
    • Y10T428/2933Coated or with bond, impregnation or core
    • Y10T428/2964Artificial fiber or filament
    • Y10T428/2967Synthetic resin or polymer
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber
    • Y10T428/2933Coated or with bond, impregnation or core
    • Y10T428/2964Artificial fiber or filament
    • Y10T428/2967Synthetic resin or polymer
    • Y10T428/2969Polyamide, polyimide or polyester
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2418Coating or impregnation increases electrical conductivity or anti-static quality
    • Y10T442/2451Phosphorus containing

Description

United States Patent ANTISTATIC SYNTHETIC TEXTILE MATERIAL Hermann Haas, Hans Markert, and Gustav Lietz, Dusseldorf, Germany, assignors to Biihme Fettchemie G. m. b. H., Dusseldorf, Germany, a corporation of Germany No Drawing. Application December 16, 1954 Serial No. 475,812

Claims priority, application Germany December 21, 1953 4 Claims. (Cl. 117-1395) This invention relates to antistatic preparations and to a process of treating textile materials, and more particularly synthetic textile materials or mixtures of synthetic and natural fibers, with such preparations so as to pre vent generation and accumulation of static electricity in said textile materials.

It is known that textile materials composed of synthetic fibers often accumulate disturbing electric charges on working and processing or using such materials. This property of generating and accumulating static electricity is especially pronounced in materials made from polycondensationproducts, such as polyesters, polyamides, and the like; from vinyl polymerization products, such as polyvinyl chloride, polyvinyl acetate, and the like; from polymers of acrylic acidderivativeasuch as polymers of acrylic acid esters, acrylonitrile, and the like. Natural fibers containing nitrogen, such as silk and wool, are also subject to the generation and accumulation of static electrical charges at least to a certain extent.

Generation of static electricity and accumulation of electric charges considerably interfere with mechanical processing of said materials and are an inconvenience in their use. For example, in carding, drawing and spin-,

ning of such fibers, static electricity can be generated to such an extent that further processing will be rendered impossible because, due to such accumulation of electric charges, the individual fibers are caused to spread, loose fibers may be attracted to or repeiled from the fibers being worked and the spinning material may become wrapped upon rotating parts of the processing machines. Woven and knitted fabrics made from such fibers can often be processed and packed only with great difiiculty. -.On Wearing finished garments of ,such materials, such garments either adhere and cling to each other and to the wearer or they repel each other in an undesired and objectionable manner. I

It is one object of the present invention to provide a simple and effective process of preventing generation and accumulation of static electricity in textile materials, or of eliminating or at least considerably reducing static charges generated or accumulated therein.

Another object of the present invention is to provide preparations for the treatment of synthetic fiber materials, which preparations prevent generation and accu- .mulation of static electricity in said fibers on subsequent spinning and further processing.

A further object of the present invention is to provide an impregnating preparation for the treatment of finished woven or 'knitted fabrics made of synthetic fiber material, said impregnating preparation safeguarding such fabrics against accumulation of static charges.

Still another object of the present invention is to provide synthetic. fiber material which is substantially free of static electricity and does not develop static charges on processing it and on wearing garments or using products made therefrom.

Various other objects and advantages of our invention will become apparent as this description proceeds.

ice

In principle, the present invention consists in treating the textile material during its manufacture, during processing and finishing, or during its use with neutral alkylene oxide addition compounds of acid phosphoric acid esters of higher molecular hydroxyl compounds. As a result of such a treatment, generation and accumulation of static electricity in said textile materials are prevented or at least reduced to such an extent that it has no more disturbing effect on processing and using said materials.

The antistatic preparations used for the treatment of textile materials and more particularly of synthetic textile materials are preferably aqueous solutions or dispersions of such alkylene oxide addition compounds of acid phosphoric acid esters of higher molecular hydroxyl compounds. contain at least about 1 g. of said addition compounds per liter. Amounts between about 1 g. and about 50 g. per liter are ordinarily suflicient to produce the desired effect. Higher concentrations may, of course, also be employed but usually will serve no useful purpose.

It is understood that the concentration of the addition compound in the aqueous solution or dispersion depends upon the type of textile material to be treated and the method of treatment to be employed. It is readily possible to determine by simple preliminary tests the optimum concentration of the addition compound which should be used for each preparation, for each textile material and for each method of treatment.

One of the methods advantageously used in this treatment comprises spraying or sprinkling the fiber material, for instance, in the form of staple fiber on conveyor belts, with antistatic solutions or dispersions according to the present invention, or the textile material may be sprayed therewith in suitable chambers from which unabsorbed,

treatment material may be recovered, or it may be dipped or immersed into said solutions or dispersions.

The antistatic treatment can also be effected during winding, spooling, doubling, twisting, and the like operations, by using spooling and spinning oils containing such antistatic addition compounds.

Where necessary, known emulsifier and dispersing agents may be added to the antistatic preparations according to the present invention; also hygroscopic agents, lubricants, brightening agents andother agents facilitating further processing and imparting to the treated textile materials additional improving effects may be used. Mineral, animal or vegetable oils, fats or waxes which are held in emulsion by said antistatic alkylene oxide addition compounds may be used as lubricants in the textile processing operations. may be employed, for instance, glycerol, glycols, urea or hygroscopic inorganic salts, together with the alkylene oxide antistatic agents described herein.

The acid phosphoric acid esters used in the production of the alkylene oxide addition compounds forming the basis of the new antistatic preparations described herein may be produced according to methods known per se, for instance, by esterifying higher molecular alcohols with phosphorus .pentoxide, pyrophosphori-c acid, metaphosphoric acid and other phosphoric acids containing less water in their molecule than pyrophosphoric acid, as well as with mixtures of such acids or With phosphorus oxychloride.

Said acid esters are converted into their alkylene oxide addition compounds, i. e. the corresponding neutral mixed 7 esters, by the addition of alkylene oxides, especially of ethylene oxide, at a temperature between about 50C. and about C. in the absence of catalysts. Thereby l to 4 or even more mols of ethylene oxide are added to each available acid group of the ester used as one of the reaction components.

As starting materials for the preparation of the acid Such aqueous solutions or dispersions must As hygroscopic agents there ass-aces phosphoric acid esters there are employed aliphatic, cycloaliphatic, cycloaliphatic-aromatic, and aliphatic-aromatic hydroxyl compounds with at least 6 carbon atoms in their molecule, such as hexanol, octanol, dodecanol, oleyl alcohol, octadecanol, cyclohexancl, alkyl cyclohexyl alcohols, naphthene alcohols, benzyl alcohol, tetrahydronaphthol, decahydronaphthol, alkyl phenols and the like hydroxyl compounds. The hydroxyl compounds may also contain substituents or their hydrocarbon chain may be interrupted by hetero atoms, such as oxygen, sulfur, or nitrogen, or by hetero atom groups derived from said hetero atoms.

As alkylene oxide there is primarily used ethyl ne oxide, but propylene oxide, glycide, and the like alkylene com pounds may also be employed.

Alkylene oxide addition compounds of acid phosphoric acid esters as they are contained in antistatic preparations produced according to the present invention may be, for instance, the following compounds:

The condensation product of 2 mols of a technical grade mixture of hexadecanol and octadecanol with 1 mol of phosphorus pentoxide and 5 to 7 mols of ethylene oxide; the condensation product of 2 mols of octadecanol with 1 mol of phosphorus pentoxide and 4 to 8 mols of ethylene oxide; the condensation product of 1.5 mols of dodecanol with 1 mol of phosphorus pentoxide and 6 to 10 mols of ethylene oxide; and similar compounds based upon the use of hydroxyl compounds such as specified above.

The following examples serve to illustrate the present invention without, however, limiting the same thereto.

Example I Cut staple fibers of polyvinyl chloride, polyamides, polyacrylonitrile, or polyesters are treated with an aqueous dispersion containing 5 g. per liter of a condensation product of 2 mols of a mixture of fatty alcohols having 16 and 18 carbon atoms in their molecules, 1 mol of phosphorus pentoxide, and 4 to 6 mols of ethylene oxide by sprinkling the fibers on a conveyor sit with said aqueous dispersion. Thereafter the treated fibers are centrifuged and dried in a conventional manner.

The resulting fibers do not generate and accumulate static electricity and can be processed with great ease by spinning.

Example II 'mixture (3 ,43 1 mol of phosphorus pentoxide, and 4 to 8 mols of ethylene oxide. in this manner, antistatic finished yarns of excellent closeness of the twist and good elastic properties are obtained.

Example III For-spinning synthetic fibers as set forth in Example I in mixture with natural fibers such as wool or cotton, wool oils and spinning oils prepared, for instance, on the basis of fatty acids, fatty acid glycerides, and/ or mineral oils, are conventionally used. According to the present invention 2% to 5% of the condensation product of 2 mols of decanol, 1 mol of phosphorus pentoxide, and 4 to 8 mols of ethylene oxide are added to such wool oils and spinning oils and are finely and uniformly dispersed therethrough. The resulting preparations not only impart satisfactory antistatic properties to yarns spun therewith but also excellent resistance against distortion and draft and warping, and yield yarns of uniform quality.

4 l Example IV Finished woven or knitted fabrics made of synthetic fibers of the classes heretofore set forth are impregnated with an aqueous dispersion of the condensation product of 2 mols of a mixture of fatty alcohols having 16 and 18 carbon atoms in their molecules, 1 mol of phosphorus entoxide, and 4 to 6 mols of ethylene oxide, said dispersion containing 30 g. of said condensation product per liter. impregnation is effected by treatment on a Foulard machine or similar sizing or impregnating device. The impregnated fabrics do not generate static electricity on friction and have an agreeable feel similar to that of natural fibers.

it is to be understood that many changes and variations in the composition of the antistatic preparations, in the components forming the neutral alkylene oxide addition compounds of acid phosphoric acid esters of higher molecular organic hydroxyl compounds, in the amounts of said addition compounds present in said preparations, in the methods of treating textile materials with said preparations, and in other features of our invention may be made without departing from the spirit of our invention or the scope of the following claims.

We claim:

1. An antistatic synthetic textile material impregnated with a neutral condensation product, formed by esterifying 1 mol prosphorus pentoxide with 2 mols of fatty alcohol with from 6 to 18 carbon atoms, and subjecting the resulting acid phosphoric acid ester to a condensation reaction with from 1 to .10 mols ethylene oxide at a temperature between 50 and'l00 C., in an amount sulficient to impart antistatic properties to said synthetic textile material. j

2. An antistatic synthetic textile material impregnated with a neutral condensation product, formed by esterifying 1 mol phosphorus pentoxide with 2 mols of a mixture of fatty alcohols having from 16 to 18 carbon atoms, and subjecting the resulting acid phosphoric acid ester to a condensation reaction with 4 to 6 mols ethylene oxide at a temperature between 50 and C., in an amount sufficient to impart antistatic properties to said synthetic textile material.

3. An antistatic synthetic textile material impregnated with a neutral condensation product, formed by esterifying 1 mol phosphorus pentoxide with 2 mols of a mixture of fatty alcohols having from 12 to l8 carbon atoms, and subjecting the resulting acid phosphoric acid ester to a condensation reaction with 4 to 8 mols ethylene oxide at a temperature between 50 and 100 C., in a suflicient amount to impart antistatic properties to the textile material.

4. An antistatic synthetic textile material impregnated with a neutral condensation product, formed by esterifying 1 mol phosphorus pentoxide with 2 mols decanol, and subjecting the resulting acid phosphoric acid ester to a condensation reaction with 4 to 8 mols ethylene oxide at a temperature between 50 and 100 C., in an amount sufiicient to impart antistatic properties to the textile material.

References Cited in the file of this patent UNITED STATES PATENTS 1,970,578 Schoeller et al. Aug. 21, 1934 2,676,122 McCarthy Apr. 20, 1954 2,729,576 Tiusler Jan. 3, 1956 FOREIGN PATENTS 498,262 Belgium Oct. 14, 1950

Claims (1)

1. AN ANTISTATIC SYNTHETIC TEXTILE MATERIAL IMPREGNATED WITH A NEUTRAL CONDENSATION PRODUCT, FORMED BY ESTERIFYING 1 MOL PROSPHORUS PENTOXIDE WITH 2 MOLS OF FATTY ALCOHOL WITH FROM 6 TO 18 CARBON ATOMS, AND SUBJECTING THE RESULTING ACID PHOSPHORIC ACID ESTER TO A CONDENSATION REACTION WITH FROM 1 TO 10 MOLS ETHYLENE OXIDE AT A TEMPERATURE BETWEEN 50 AND 100*C., IN AN AMOUNT SUFFICIENT TO IMPART ANTISTATIC PROPERTIES TO SAID SYNTHETIC TEXTILE MATERIAL.
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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2948697A (en) * 1958-04-23 1960-08-09 Du Pont Plasticized polyvinyl alcohol composition
US2979523A (en) * 1956-03-06 1961-04-11 Gulf Oil Corp Addition products of dialkyl acid orthophosphate and olefin oxides
US2979478A (en) * 1958-04-01 1961-04-11 Virginia Carolina Chem Corp Composition containing polyvinyl alcohol and a neutral ester of phosphoric acid
US2990421A (en) * 1958-04-01 1961-06-27 Virginia Carolina Chem Corp Neutral esters of phosphoric acid
US3016333A (en) * 1958-10-31 1962-01-09 American Cyanamid Co Method of treating hair with hydroxyether amides of polyacrylic acids
US3061625A (en) * 1961-06-15 1962-10-30 Weston Chemical Corp Phosphates and thiophosphates
US3094549A (en) * 1961-07-27 1963-06-18 Dow Chemical Co Process for preparing hydroxyalkyl phosphates
US3170877A (en) * 1961-12-21 1965-02-23 Gen Aniline & Film Corp Antistatic treating solution for polyacrylonitrile fibers and method
US3228998A (en) * 1960-10-17 1966-01-11 Union Oil Co Liquid polyphosphate esters
US3341343A (en) * 1963-11-12 1967-09-12 Gen Anilline & Film Corp Hydrophobic polymeric resin containing phosphate ester antistatic agent and process for producing antistatic properties
US3341451A (en) * 1964-03-06 1967-09-12 Courtaulds Ltd Textile processing agents
US3346667A (en) * 1963-09-06 1967-10-10 Francis G Firth Product produced by reacting phosphorus oxide or sulfide, an oxirane compound, and ahydroxy or thiol compound together, and process
US3428481A (en) * 1966-07-06 1969-02-18 Du Pont Antistatic lubricating composition for textile fibers
US3439068A (en) * 1965-05-21 1969-04-15 Olin Mathieson Process for stabilizing a polyol phosphorus by adding limonene dioxide,vinylcyclohexene dioxide or dicyclodiepoxy carboxylate and composition
US3770495A (en) * 1968-01-08 1973-11-06 H Lenz Non-adhesive high elastic elastomer threads
US3907689A (en) * 1973-08-29 1975-09-23 Eastman Kodak Co Textile treating composition and textile yarn treated therewith
US3926816A (en) * 1970-05-22 1975-12-16 Goulston Co George A Textile fiber lubricants
US4039715A (en) * 1973-08-29 1977-08-02 Eastman Kodak Company Textile treating composition and textile yarn treated therewith
US4165303A (en) * 1974-01-16 1979-08-21 Emery Industries, Inc. Polymer compositions containing poly (alkylene ether) esters of polybasic acids
US4210700A (en) * 1978-09-15 1980-07-01 Allied Chemical Corporation Production of polyester yarn
US5972497A (en) * 1996-10-09 1999-10-26 Fiberco, Inc. Ester lubricants as hydrophobic fiber finishes

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DE1084231B (en) * 1957-06-28 1960-06-30 Glanzstoff Ag A process for the antistatic finishing agent of Polyaethylenterephthalatfaeden or fibers
DE1090170B (en) * 1958-12-12 1960-10-06 Basf Ag Antistatics
BE582924A (en) * 1958-12-13
NL245071A (en) * 1959-01-07

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US2676122A (en) * 1951-01-09 1954-04-20 Du Pont Antistatic treatment of hydrophobic fiber
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US2676122A (en) * 1951-01-09 1954-04-20 Du Pont Antistatic treatment of hydrophobic fiber
US2729576A (en) * 1953-09-29 1956-01-03 Davies Young Soap Company Method of dry cleaning fabric and simultaneously rendering the same antistatic

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2979523A (en) * 1956-03-06 1961-04-11 Gulf Oil Corp Addition products of dialkyl acid orthophosphate and olefin oxides
US2979478A (en) * 1958-04-01 1961-04-11 Virginia Carolina Chem Corp Composition containing polyvinyl alcohol and a neutral ester of phosphoric acid
US2990421A (en) * 1958-04-01 1961-06-27 Virginia Carolina Chem Corp Neutral esters of phosphoric acid
US2948697A (en) * 1958-04-23 1960-08-09 Du Pont Plasticized polyvinyl alcohol composition
US3016333A (en) * 1958-10-31 1962-01-09 American Cyanamid Co Method of treating hair with hydroxyether amides of polyacrylic acids
US3228998A (en) * 1960-10-17 1966-01-11 Union Oil Co Liquid polyphosphate esters
US3061625A (en) * 1961-06-15 1962-10-30 Weston Chemical Corp Phosphates and thiophosphates
US3094549A (en) * 1961-07-27 1963-06-18 Dow Chemical Co Process for preparing hydroxyalkyl phosphates
US3170877A (en) * 1961-12-21 1965-02-23 Gen Aniline & Film Corp Antistatic treating solution for polyacrylonitrile fibers and method
US3346667A (en) * 1963-09-06 1967-10-10 Francis G Firth Product produced by reacting phosphorus oxide or sulfide, an oxirane compound, and ahydroxy or thiol compound together, and process
US3341343A (en) * 1963-11-12 1967-09-12 Gen Anilline & Film Corp Hydrophobic polymeric resin containing phosphate ester antistatic agent and process for producing antistatic properties
US3341451A (en) * 1964-03-06 1967-09-12 Courtaulds Ltd Textile processing agents
US3439068A (en) * 1965-05-21 1969-04-15 Olin Mathieson Process for stabilizing a polyol phosphorus by adding limonene dioxide,vinylcyclohexene dioxide or dicyclodiepoxy carboxylate and composition
US3428481A (en) * 1966-07-06 1969-02-18 Du Pont Antistatic lubricating composition for textile fibers
US3770495A (en) * 1968-01-08 1973-11-06 H Lenz Non-adhesive high elastic elastomer threads
US3926816A (en) * 1970-05-22 1975-12-16 Goulston Co George A Textile fiber lubricants
US3907689A (en) * 1973-08-29 1975-09-23 Eastman Kodak Co Textile treating composition and textile yarn treated therewith
US3951825A (en) * 1973-08-29 1976-04-20 Eastman Kodak Company Textile treating composition and textile yarn treated therewith
US4039715A (en) * 1973-08-29 1977-08-02 Eastman Kodak Company Textile treating composition and textile yarn treated therewith
US4165303A (en) * 1974-01-16 1979-08-21 Emery Industries, Inc. Polymer compositions containing poly (alkylene ether) esters of polybasic acids
US4210700A (en) * 1978-09-15 1980-07-01 Allied Chemical Corporation Production of polyester yarn
US5972497A (en) * 1996-10-09 1999-10-26 Fiberco, Inc. Ester lubricants as hydrophobic fiber finishes

Also Published As

Publication number Publication date Type
FR1115874A (en) 1956-04-30 grant
GB769039A (en) 1957-02-27 application

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