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Publication numberUS2837446 A
Publication typeGrant
Publication dateJun 3, 1958
Filing dateJun 11, 1956
Priority dateAug 31, 1951
Publication numberUS 2837446 A, US 2837446A, US-A-2837446, US2837446 A, US2837446A
InventorsOscar P Cohen, Milton J Scott
Original AssigneeMonsanto Chemicals
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Textile materials with an anti-static finish and process of making same
US 2837446 A
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Description  (OCR text may contain errors)

TEXTILE MATERIALS WETH AN ANTI-STATIC FINISH AND PROCESS OF MAKlNG SAW Oscar P. Cohen, Longmeadow, and Milton J. Scott, Lexington, Mass., assiguors to Monsanto Chemical {Ionipany, St. Louis, Mo., a corporation of Delaware No Drawing. Original application August 31, 1951, Se-

rial No. 244,730. Divided and this application June 11, 1956, Serial No. 590,362

15 Claims. (Cl. 117-1385) The present invention relates to the treatment of synthetic polymer textile materials, particularly unspun fibers composed wholly or partly of fiber-forming synthetic polymers, and to the textile materials so produced.

It is one object of this invention to provide improved processes for treating synthetic polymer textile materials, particularly unspun fibers composed wholly or partly of fiber-forming synthetic polymers, to render the textile materials more amenable to mechanical processing.

It is a further object of this invention to provide improved processes for treating synthetic polymer textile materials, particularly unspun fibers composed wholly or partly of fiber-forming synthetic polymers, to provide such materials with a soft, anti-static finish or dressing.

It is a further object of this invention to provide synthetic polymer textile materials, particularly unspun fibers composed wholly or partly of fiber-forming synthetic polymers, having a soft, anti-static finish or dressmg.

Still further objects and advantages of this invention will become apparent in the following description and the appended claims.

The objects of this invention are attained, in general, by applying a quaternary phosphonium salt to a synthetic polymer textile material. The amount of quaternary phosphonium salt applied may vary considerably but should be sutficient to minimize the formation of static electricity on such textile materials during the handling or manipulation of the textile materials.

The term textile materials as used in the specification and the appended claims is intended to include undyed or dyed unspun fibers, yarns, continuous filaments or fabrics comprising at least by Weight of a fiberforming synthetic polymer. The processes of this invention are particularly applicable to the treatment of unspun fibers comprising at least 10% by weight of unspun staple fibers of a fiber-forming synthetic polymer to render fibers amenable to spinning and to minimize the formation of static electricity on such fibers during the processing of such fibers preparatory to spinning the fibers into yarns. Accordingly, the treatment of such unspun fibers is preferred. 4

As examples of fiber-forming synthetic polymers which are included in the textile materials defined above may be mentioned the fiber-forming copolymers of vinyl chloride and vinyl acetate; the fiber-forming polymers of vinylidene chloride and copolymers of a major proportion of vinylidene chloride and a minor proportion of an unsaturated compound copolymerizable therewith having the grouping CH such as, for example, vinyl compounds including vinyl chloride; fiber-forming linear polyesters of glycols such as ethylene glycol and terephthalic acid; fiber-forming homopolymers of acrylonitrile and heteropolymers containing combined acrylonitrile such as, for example, heteropolymers of a major proportion of acrylonitrile and a minor proportion of an' unsaturated organic compound copolymerizable therewith having the grouping CH including such compounds as styrene, alkyl and halogen nuclear substituted styrene, vinyl chloride, alkyl acrylates such as methyl or ethyl acrylate, alkyl methacrylates such as methyl or ethyl methacrylates, vinyl pyridine, divinyl benzene and the like; and fiber-forming linear polyamides such as, for example, polyhexamethylene-adipamide, polyhexamethylene-sebacamide and the fiber-forming linear polyamides described in United States Patents No. 2,071,250, No. 2,130,532 and No. 2,130,948. Mixtures of such fiber-forming synthetic polymers may also be used.

The processes of this invention are more particularly suitable for the treatment of unspun staple fibers containing at least 10% by weight of polyhexamethyleneadipamide staple fibers or staple fibers of polyacrylonitrile or fiber-forming heteropolymers containing combined acrylonitrile, or mixtures of such staple fibers. Accordingly, the treatment of these specific staple fibers is preferred.

As examples of textile fibers, yarns or filaments which may be combined With the synthetic polymer materials to form the textile materials defined above may be mentioned fibers, yarns or continuous filaments of natural cellulose materials such as cotton, linen, ramie or the like, synthetic regenerated cellulose materials such as viscose rayon, cuprammonium rayon and saponified cellulose acetate; natural or synthetic proteinaceous materials such as wool, or animal fibers, casein, peanut protein and the like; and cellulose derivative materials such as cellulose esters derived from cellulose and an aliphatic acid as, for example, cellulose acetate, and water-insoluhle cellulose ethers. Mixtures of fibers, yarns and continuous filaments of such materials may also be used with the fiber-forming synthetic polymer materials.

The quaternary phosphonium salts may be applied to the textile materials defined above in various ways. Thus, organic solvent solutions or aqueous solutions or dispersions of the quaternary phosphonium salts may be sprayed or dripped on the textile materials, or the textile materials may be immersed in such solutions or dispersions, or thetextile materials, particularly in the case of yarns or filaments, may be passed over a roller coated with such solutions or dispersions. method of application employed will vary depending on the form of the textile used. Thus, in the case of unspun textile fibers, the fibers are usually treated by immersing them in or spraying them with the solutions or dispersions of the quaternary phosphonium salts, although such fibers may also be treated by a dripping process. In the case of yarns or filaments it is preferred to pass such materials over a roll which is coated With a solution or dispersion of the quaternary phosphonium salt, or by immersing the yarns or filaments in a solution or dispersion of such salt and then removing the excess solution or dispersion by squeezing or centrifuging, or by means of suction or compressed air. Fabrics are preferably treated by a padding operation in which the fabrics are first immersed in a solution or dispersion of the quaternary phosphonium salt and then passed between squeeze rolls to remove excess solution or dispersion. Fabrics may, however, be treated by spraying, or they may be treated in conventional dyeing apparatus. For convenience of application it is preferred to use aqueous solutions or dispersions of Water-soluble quaternary phosphonium salts.

The term solution as used in the appended claims is intended to include true solutions, stable colloidal solutions and stable dispersions since it is believed that in some instances the quaternary phosphonium salts are present in the liquid phase as a solute, colloid and as a disperse phase.

The solutions or dispersions of thequaternary phosphonium salts employed herein may comprise small The particularamounts, say from about 0.01 to 5% by weight of conventional textile assistants or adjuvants, as for example, lubricants such as mineral oils, vegetable oils, sulfonated or sulfated mineral oils or vegetable oils, butyl stearate, mixtures of suchmaterials, including oil-dispersible or water-dispersible mixtures and the like; humectantssuch as sorbitol, glycerine and the like; dispersing agents such as sorbitol laurate and ethylene oxide-alkyl mercaptan condensation products, in which the alkyl group contains at least 8 carbon atoms; monchydric compounds such as butyl alcohol, 2-ethoxyethanol diethylene glycol ethyl ether and the like; and wetting agents such as ammonium stearate.

Regardless of the mode of applying the solutions or dispersions of the quaternary phosphonium salts to the textile material, it is necessary to deposit on the textile material an amount of the quaternary phosphonium salt sufiicient to minimize the formation of static electricity on such textile materials during subsequent processing operations. Usually the application of from about 0.01 to 5% by weight of the quaternary phosphonium salts, on the dry weight of the textile materials, will give satisfactory results. However, it is always possible to apply larger amounts of such salts, for example, up to 10% byweight based on the dry weight of the textile: material. Best results are obtained by applying from about 0.3 to 3% by weight of the quaternary phosphonium salt, based on the dry weight of textile materials, and such amounts are accordin ly preferred.

In order to obtain the desired anti-static effects on the treated textile materials, it is essential that the textile material contain a continuous coating or deposit of the quaternary phosphonium salt on the surface of the material.

The above described amounts of quaternary phosphoniurn salts are applied to the textile materials by properly adjusting the concentration of the salt in the solution which is applied to the textile materials, or by adjusting the concentration of salt in the solution which is applied and then squeezing, centrifuging, sucking or blowing the excess solution from the textile materials. In general, a solution containing from about 0.01 to 10% by weight of the quaternary phosphonium salt will deposit the de sired amounts of the salt within the ranges specified above, depending on the amount of pick up obtained.

After the textile materials have been treated as described above, they are normally dried either by allowing the materials to dry at ordinary room. temperatures or by heating the textile materials in a current of warm or hot air, for example, at temperatures of 110 to 200 F. This is the normal procedure in the treatment of unspun fibers, yarns or filaments and is usually the procedure followed in the treatment of fabrics.

By carrying out the processes described herein, it is possible to provide synthetic polymer textile materials, as hereinbefore defined, having a finish which is soft and has anti-static properties, that is, the property of substantially preventing the build-up of static electric charges on the dry textile materials during manipulation or handling.

A further understanding of the processes and textile materials described herein will be obtained from the following specific examples which are intended to illustrate this invention, but not to limit the scope thereof, parts and percentages being by weight unless otherwise specified.

Example I Polyhexamethyiene-adipamide continuous filaments were immersed in a 2% water solution of benzyl tris (dimethylamino) phosphonium chloride and squeezed between pad rolls to obtain a pick up of 80% of the solution, based on the dry filament weight. The filaments ere then air dried at a temperature of about 70 R,

after which they were spun into plied yarns. The filaments did not accumulate static electric charges, whereas equivalent filaments which were not treated with the phosphonium salts accumulated a noticeable charge of static electricity during the spinning of the plied yarns.

Example II A woven fabric consisting of polyhexamethylene-adipamide filaments in the warp and filling, and having a static charge of 148 microamperes as measured on a Hay-eh mailetester, was immersed in a 2% water solution of benzyl tris (dimethylamino) phosphonium chloride, after which it was passed between pad rolls to obtain a pick up of the solution, based on the dry fabric weight. The fabric was then air dried at a temperature of F. The resulting fabric had a zero static charge as measured on a Hayek static tester as compared to the 148 microampere charge on the untreated fabric.

The Hayek static tester which is referred to in the foregoing example and which is also referred to in Example HI is described in the American Dyestuff Reporter, volume 40, No. 5 (March 5, 1951).

Example III A woven fabric consisting of yarns prepared entirely of staple fibers of a fiber-forming heteropolymer of acrylonitrile and 15% vinyl chloride, and having a static charge of 25 microamperes as measured on a Hayek static tester, was immersed in a 5% water solution of cetyl tris (dimethylamino) phosphonium bromide, after which it was passed between pad rolls to obtain a pick up of 70% of the solution, based on the dry weight of the fabric, and the fabric was then allowed to air dry at a temperature of 70 F. The resulting fabric had a zero static charge as measured on a. Hayek static tester as compared to the 25 microa-mpere charge on the untreated fabric.

Example 1V Unspun fibers consisting of a mixture of 50% wool and 50% staple fibers of a heteropolyrner of 85% acrylonitrile and 15% styrene were sprayed with a water solution containing 2% by weight of benzyl tris (dirnethylamino) phosphonium bromide until the fibers contained 100% of the solution, based on the dry weight of the fibers. The fibers were then allowed to dry at a temperature of 80 F. The resulting fibers were then processed into yarns in accordance with the American wool spinning system. The textile fibers did not accumulate static electric charges during the processing and spinning operations, Whereas an equivalent mixture of fibers which were not treated with the quaternary phosphonium salt accumulated a static charge which interfered considerably with the rocessing and spinning of the fibers.

Example V Unspun staple fibers consisting of a fiber-forming heteroplymer of acrylonitrile and 5% vinyl pyridine were treated by dripping a 4% Water solution of cetyl tris (dimethylamino) phosphonium chloride on the fibers until they contained of the solution, based on thedry weight of the fibers. The fibers were then dried at a temperature of 75 F. and then processed into yarns in accordance with the American wool spinning system. The treated fibers did not accumulate static electric charges during the processing and spinning of the fibers,

whereas identical fibers which had not been treated with the quaternary phosphonium salt accumulated electric charges which interfered appreciably with the processing and spinning of the fibers.

In addition to providing; a soft, anti-static finish on linear polyamide textile materials as hereinbefore described, it has'presently been found that the quaternary phosphonium salts also serve to improve the depth of,

dye shade on such textile materials when' the materials are dyed with acid dyestuffs or mordant acid dyestuffs in the presence of such quaternary phosphonium salts. In carrying out this embodiment of the invention it is possible to apply the quaternary phosphonium salt to the linear polyamide textile material prior to the dyeing operation or the quaternary phosphonium salt may be added to the dye bath in the concentrations hereinbefore specified. The dyeing operation is carried out by heating the dye bath at elevated temperatures, for example, above 150 F. and preferably at the boil, until the desired dye shade has been obtained, after which the dyed material is rinsed with water and dried. The dye bath may contain the common dye bath additives such as alkali metal salts, for example, sodium sulfate or sodium chloride to assist in exhausting the dye on the textile material. The following example serves to illustrate this embodiment of the present invention.

Example VI Filaments consisting of polyhexamethylene-adipamide were immersed in an aqueous bath containing 4% Pontachrome Black TA (Colour Index Number 203), 5% acetic acid, /2 xylyl tris (dimethylamino) phosphonium bromide and glauber salt. The bath which was originally at a temperature of 100 F. was heated to a temperature of 190 F. After the bath was maintained at 190 F. for 20 minutes 2% of concentrated sulfuric acid was added and this was repeated 20 minutes later. The bath was maintained at 190 F.'for a total period of 60 minutes, after which the filaments were removed from the bath, rinsed in cold water and dried at 180 F. The resulting filaments had an excellent depth of dye shade in contrast to filaments dyed without the phosphonium salt, and also possessed a soft, anti-static finish.

A wide variety of quaternary phosphonium salts may be used in the processes of this invention, including the quaternary phosphonium chlorides, bromides, iodides, fluorides, sulfates, aliphatic monocarboxylates containing from 8 to 24 carbon atoms such as the stearates, oleates, palmitates and the like. The quaternary phosphonium aliphatic monocarboxylates are normally oilsoluble and water-insoluble but are dispersible in water with the aid of dispersing agents. Such phosphonium carboxylates are readily prepared, for example, by reacting a water-soluble salt of an aliphatic monocarboxylic acid containing from 8 to 24 carbon atoms as, for example, sodium oleate or sodium stearate with a quaternary phosphonium halide. The quaternary phosphonium chlorides and bromides are particularly suitable because they are easily prepared and are preferred over the iodides, fluorides and other water-soluble phosphonium salts. A class of compounds which may be used are thelclass of compounds represented by the general formula:

phosphonium bromide, cetyl trimethyl phosphonium stearate and the like.

Another class of quaternary phosphonium salts which may be .used are compounds represented by the general formula:

where R is an aryl-alkyl radical, R is an alkyl radical containing from 1 to 4 carbon atoms and X is a member of the class consisting of chlorine, bromine and iodine atoms and aliphatic monocarboxylate radicals containing 8 to 24 carbon atoms. This class of compounds includes benzyl trimethyl phosphonium bromide, chloride 01' iodide, benzyl triethyl phosphonium chloride or bromide and the like. I

A class of compounds which are particularly suitable in the processes of this invention is the class of nitrogencontaining phosphonium compounds represented by the general formula:

where R is an .alkyl radical containing from 6 to 22 carbon atoms, R' is an alkyl radical containing from 1 to 4 carbon atoms and X is a chlorine or bromine atom or an aliphatic monocarboxylate radical containing 8 to 24 carbon atoms. This class of compounds which may be designated alkyl tris (dialkylamino) phosphonium chlorides, bromides or aliphatic monocarboxylates,'includes such compounds as cetyl tris (dimethylamino) phosphonium chloride or bromide, dodecyl tris (dimethylamino) phosphonium chloride or bromide, n-hexyl tris (dipropylamino) phosphonium chloride or bromide, cetyl tris (dimethylamino) phosphonium stearate and the like. The halides are obtained by reacting an alkyl bromide or chloride containing from 6 to 22 carbon atoms with a hexa-alkyl phosphorous triamide having the formula: P (NR' where R has the significance described above. This reaction is normally carried out at a temperature between about 80 and 250 C, until the corresponding phosphonium halide is formed. Further examples of such halides and methods of preparing them are set forth in the copending application Serial No.

239,175 of William T. Dye, .Tr., filed July 28, 1951, and now abandoned.

A preferred class of quaternary phosphonium salts for use in the processes of this invention is the class of nitrogen-containing phosphonium compounds represented by the general formula:

where R and R are chlorine, bromine and hydrogen atoms or alkyl radicals containing from 1 to 5 carbon atoms, R" represents an alkyl radical containing from 1 to 4 carbon atoms and X is a chlorine or bromine atom or an aliphatic monocarboxylate radical containing 8 to 24 carbon atoms. As examples of this class of compounds may be mentioned benzyl tris (dimethylamino) phosphonium chloride or bromide, benzyl tris (diethylamino) phosphonium chloride orbromide, 4-ethy1 benzyl tris (dimethylamino) phosphonium chloride or bromide, 2-chlorobenzyl tris (diisopropylamino) phosphonium chloride or bromide, 3-bromobenzy1 tris (diethylamino) phosphonium chloride or bromide, benzyl tris (dimethylamino) phosphonium stearate and the like. The benzyl tris (dimethylamino) phosphonium chloride and bromide are easy to prepare, and give excellent results, Accordingly, such compounds are preferred.

The halides of the class of compounds described im mediately above are prepared, in general, by reacting the corresponding benzyl halide with a hexa-alkylphosphorous triamide in which the alkyl group contains from 1 to 4 carbon atoms. This reaction may be carried out at normal or elevated temperatures in the presence or absence of solvents or diluents. Further examples of this class of compounds and methods for preparing such compounds are given in the copending application Serial No. 223,449 of William T. Dye, Ir., filed April 27, 1951, and now abandoned.

A wide variety of acid dyestuffs or mordant acid dyestuifs may be used instead of the dyestutf employed in Example VI. As examples of such. dyestuffs may be mentioned the following:

Other suitable acid and mordant acid dyestufls will be apparent to those skilled in the art.

Various modifications and changes may be made in the processes and textile products described herein as will be apparent to those skilled in the art to which this invention appertains without departing from the spirit and intent of the invention described herein. It is accordingly understood that it is not intended to limit this invention execept by the scope of the appended'claims.

This application is a division of our copending application Serial No. 244,730, filed August 31, 1951;

What is claimed is:

1. Textile materials consisting of textile fibers, of which at least by weight are fiber-forming synthetic polymer fibers, and a quaternary phosphonium salt distributed continuously on the surface of said textile fibers, said salt being present on said materials in an amount sufi'icient to provide an anti-static finish and having the general formula:

where R is an alkyl radical containing from 6 to 22 carbon atoms, R is an alkyl radical containing from 1 to 4 carbon atoms and X is selected from the group consisting of chlorine and bromine atoms and aliphatic monocarboxylate radicals containing 8 to 24 carbon atoms.

2. Textile materials consisting of textile yarns, of which at least 10% by weight are fiber-forming synthetic polymer fibers, and a quaternary phosphonium salt distributed continuously on the surface of said yarns, said salt being present on said yarns in an amount sufiicient to provide an anti-static finish and having the general formula:

nae NR:

where R is an alkyl radical containing from 6 to 22 carbon atoms, R is an alkyl radical containing from 1 to 4 carbon atoms and X is selected from the group consisting of chlorine and bromine atoms and aliphatic monocarboxylate radicals containing 8 to 24 carbon atoms.

3. Unspun textile fibers consisting of said fibers, of which at least 10% by weight are unspun fiber-forming synthetic polymer fibers, and a quaternary phosphonium salt distributed continuously on the surface of said fibers, said salt being present on the fibers in an amount sufficient-to provide an anti-static finish and having the general formula:

R X1|NR'2 NR: NR:

where R is an alkyl radical containing from 6 to 22 carbon atoms, R is an alkyl radical containing from 1 to 4 carbon atoms and X is selected from the group consisting of chlorine and bromine atoms and aliphatic monocarboxylate radicals containing 8 to 24 carbon atoms.

4. Unspun textile fibers consisting of said fibers, of

which at least 10% by weight are unspun fiber-forming synthetic polymer fibers, and cetyl tris (dimethylamino) phosphonium chloride distributed continuously on the surface of said fibers in an amount suflicient to provide an anti-static finish.

5. A process of treating textile materials comprising at least 10% by weight of a fiber-forming synthetic polymer which comprises applying to said textile materials a solution consisting of a quaternary phosphonium salt having the general formula:

where R is an alkyl radical containing from 6 to 22 carbon atoms, R is an alkyl radical containing from 1 to 4 carbon atoms and X is selected from the group consisting of chlorine and bromine atoms and aliphatic monocarboxylate radicals containing 8 to 24 carbon atoms, and a solvent for said salt, said salt being supplied. in an amount sufiicient to provide an anti-static finish on said textile materials.

6. A process as in claim 5, but further characterized in that said textile materials are textile yarns.

7. A process of treating unspun textile fibers comprising at least 10% by weight of staple fibers of a fiber-forming synthetic polymer to render said fibers more amenable to processing prior to spinning which comprises applying to said fibers a solution consisting of a quarternary. phosphonium salt having the general formula:

Where R is an alkyl radical containing from 6 to 22 car- 7 bon atoms, R is an alkyl radical containing from 1 to4 carbon atoms and X is selected from the group consisting of chlorine and bromine atoms and aliphatic monocar- 1 said chloride being supplied in an amount sufiicient to i provide an anti-static finish on said fibers.

9. A process of treating unspun textile fibers comprising at least 10% by weight of staple fibers of a fiber-forming synthetic polymer to render said fibers more amenable to processing prior to spinning which comprises applying to said fibersa solution consisting of cetyl tris (dimethylamino) ph'osphonium bromide and a solvent therefor, said bromide being supplied in an amount sufficient to provide an anti-static finish on said fibers.

10. A process of treating unspun textile fibers comprising at least 10% by weight of staple fibers of a fiber-form- 9 ing synthetic polymer to render said fibers more amenable to processing prior to spinning which comprises applying to said fibers an aqueous solution consisting of water and a Water-soluble quaternary phosphonium salt having the general formula:

N'z NR,

where R is an alkyl radical containing from 6 to 22 carbon atoms, R is an alkyl radical containing from 1 to 4 carbon atoms and X is selected from the group consisting of chlorine and bromine atoms and aliphatic monocarboxylate radicals containing 8 to 24 carbon atoms, said solution being supplied in an amount sufficient to provide from 0.01 to 10% by weight of said salt, based on the dry Weight of said fibers, and subsequently drying said fibers.

11. A process as in claim 10, but further characterized in that the textile fibers comprise at least 10% by weight of staple fibers of polyhexamethylene adipamide.

12. A process as in claim 10, but further characterized in that the textile fibers comprise at least 10% by weight of staple fibers of a fiber-forming heteropolymer containing combined acrylonitrile.

13. A process as in claim 10, but further characterized in that the textile fibers comprise at least 10% by weight of staple fibers of polyacrylonitrile.

14. A process of treating unspun textile fibers comprising at least 10% by weight of staple fibers of a fiber-forming heteropolymer containing combined acrylonitrile to render said fibers more amenable to processing prior to spinning which comprises applying to said fibers an aqueous solution consisting of Water and cetyl tris (dimethylamino) phosphonium chloride, said solution being supplied in an amount sufficient to provide from 0.01 to 10% by weight of said chloride, based on the dry weight of said fibers, and subsequently drying said fibers.

15. A process of treating unspun textile fibers comprising at least 10% by weight of staple fibers of polyhexamethylene-adipamide to render said fibers more amenable to processing prior to spinning which comprises applying to said fibers an aqueous solution consisting of water and cetyl tris (dimethylamino) phosphonium chloride, said solution being supplied in an amount sufiicient to provide from 0.01 to 10% by weight of said chloride, based on the dry weight of said fibers, and subsequently drying said fibers.

References Cited in the file of this patent UNITED STATES PATENTS 2,242,224 Bley May 20, 1941 2,254,965 Kling Sept. 2, 1941 2,543,539 Wizon Feb. 27, 1951 2,693,427 Kingsford Nov. 2, 1954 2,700,001 Cohen et al. Jan. 18, 1955 2,726,256 Morris et al. Dec. 6, 1955 2,735,790 Waitkus Feb. 21, 1956 2,742,379 Schofield Apr. 17, 1956 UNITED STATES PATENT OFFICE Certificate of Correction Patent No. 2,837 ,446 June 3, 1958 Oscar P. Cohen et a1.

It is hereby certified that error appears in the printed specification of the above numbered patent requlring correction and that the said Letters Patent should read as corrected below.

Column 1, lines 51 and 52, after render insert such; lines 64 and 72, for the chemical formula CH2= read OI-I =C in each occurrence.

Signed and sealed this 12th day of August 1958.

[SEAL] Attest: KARL H. AXLINE, Attestz'ng Ofiioer.

ROBERT C. WATSON, Commissioner of Patents.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2242224 *Nov 30, 1937May 20, 1941North American Rayon CorpSurface wetting agent and process of making it
US2254965 *Sep 18, 1934Sep 2, 1941Patcheni Ag Zur Beteiligung AnProcess for the dyeing of fibrous materials
US2543539 *Jan 28, 1949Feb 27, 1951American Cyanamid CoAntistatic treatment of shaped articles comprising a vinyl resin and treated articles
US2693427 *Jul 30, 1947Nov 2, 1954Monsanto ChemicalsTreatment of textile and cellulosic material
US2700001 *Jan 13, 1954Jan 18, 1955Monsanto ChemicalsProcess of providing textile material with an antistatic finish
US2726256 *Mar 25, 1952Dec 6, 1955Shell DevOrgano-phosphorus esters
US2735790 *Oct 20, 1954Feb 21, 1956 Ttnitehi
US2742379 *Feb 25, 1954Apr 17, 1956Du PontTreatment of textile fibers with antistatic agent and product thereof
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3062180 *Dec 22, 1958Nov 6, 1962Basic Res CorpApparatus for rendering fabrics antistatic
US3530164 *Aug 13, 1965Sep 22, 1970American Cyanamid CoFlame retardant agents for thermoplastic products
US4943380 *Feb 27, 1989Jul 24, 1990Takemoto Yushi Kabushiki KaishaHeat resistance