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Publication numberUS2735790 A
Publication typeGrant
Publication dateFeb 21, 1956
Filing dateOct 20, 1954
Priority dateOct 20, 1954
Also published asDE1046826B
Publication numberUS 2735790 A, US 2735790A, US-A-2735790, US2735790 A, US2735790A
InventorsCaiviii J. Waitkus
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Ttnitehi
US 2735790 A
Abstract  available in
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Description  (OCR text may contain errors)

United States Fame COMPOSITION "METHOD 'FOR' IMPARTING SQFTNESS AND ANTI-STATlC PROPERTIE-S TO ACRYLONITRILE FIBERS Calvin J. Waitkus, Decatur, Ala., assignorto The .Chemstrand Corporation, Decatur, Ala., .a corporation of Delaware N Drawing. Application 0ctober20, 1954, Serial No. 463,589

9..Claims. (Cl. 1317-13848) This invention relates to the treatment Ofxshaped .articles, and relatesmore particularly .to an improved process for imparting antistatic, lubricity, softness and other desirable properties to articles comprising acrylonitrile polymers, to the articles resulting from such process, and to compositions employed therein.

Acrylonitrile polymers constitute .a .class of material which develop, or tend ,to develop, an electrostatic charge upon their surfaces when fibers .or other articles made therefrom are subjected to friction during their production and during processing or fabrication of the fibers into fabrics or other articles, as well as during the use of the finished article. Before fibers :of acrylonitrile polymers are spun into yarns it is necessary to modify the electrical qualities so that the Qfibers willsgenerate a minimum amount ofelectricity during carding, combing,-

spinning, and like operations where thefibers are rubbed in constant frictional contact. The presence vofstatic electricity on the fibers [creates a severe problem, because it not only results in stielring'of the fibers to the machinery, but also tends to cause .theliihers torepel each other during suchoperations as .carding .and :drawing so that it is difiicult or impossible tospin a coherent, compact yarn from them.

Another problem of .major importance encountered with filaments and fibers of acrylonitrile polymers is to so lubricate or soften .the yarn that it will have the correct frictional characteristics, or drag, and the :required flexibility for the specific purpose vin view. In the bandling of continuous filament yarn, for:,example,-it is necessary to condition the ,material to reduce the tendency toward breakage of individual filaments when the yarn is subjected to mechanical strains such as are involved in passage of the yarn over ,guides, rolls, and other parts of the yarn-producing mechanism and in twisting, winding, reeling and similar operations. .In the case of yarns intended for use on commercialknitting machinery, it is particularly important that .the yarn be soft .and pliable in order thatit may conform to the contour of the needles and give a closely knit fabric free :from cuts, pinholes, stitch distortion, laddering, misplaits ,andother common defects.

Although shaped articles ofacrylonitrile polymers generally may be treated in accordance with :this invention for modification of their properti s, the process. is of special advantage in the treatment of fibers to render them more amenable ':to :textile processing, :and will be described in detail in connection "with :such use.

The fibers to be conditioned in accordance with this invention may be formed of ipolyacryllonitr ile, or copolymers containing at least about 80 :percent acrylonitrile and up to about 20 percent :of other :monomers copolymerizable therewith. E amples of :suitable monomers which may be copolymerized with :acrylonit-rile'to :form the fibers which can be treated in accordance with :this invention are acids :such as zacryliaehaloacrylic, and methacrylic acids; esters zsuchzas methyl, butyl, :octyl, nnethoxymethyl, and chloroethyl methacrylates and the corresponding esters of acrylic and haloacrylic acids; meth- PatentedFeb. 21, 1956 ,acrylonitrile; vinyl and vinylidine halides such as vinyl chloride, vinyl fluoride, yinylidi-ne chloride, l-fluoro-lchloroethylene; vinyl carboxylates such as vinyl acetate,

various isomeric vjnylquinolines, "the vinylimidazoles and the vinylbenzoxazoles.

The fibers or filaments mayalso the formed from a mixture of two or more of the fiberor film-forming materials. For example-thewfibers, films, or other shaped articles to be rendered conditionedmay be formed from or comprise a blend :of a base acrylonitrile polymer with other polymeric materials which :modify the base polymer in various respects, as by imparting dye-receptivity thereto, increasing the flame-resistance thereof, or increasing the hydrophylic properties of the polymer, etc. Suitable polymeric materials for blending with the base polymer, which may be polyacrylonitrile or binary or ternary copolymers of acrylonitrilewith the copolymerizable substances mentioned above are those polymeric materials which are soluble in the same solvent as the base polymerand which, when mixed with the base polymer in an amount of from about 2 :to '50 percent on the weight of :the blend, result in .a blend which forms a solution of at least 5 percent concentration in the solvent,

which solution can be formed into ifibers byconventional procedures. Suitable solvents are .dimethyl formamide, dimethyl aceta-mide, :gamma-bntyrolacetone, ethylene carbonate, and others disclosed in such patents as U. S. Nos. 2,404,712 to 2,4;()-i,:72.7; 2,498,665; 2,522,445; 2,487,859; 2,6;06,"168 and 2,496,267.

As an iilustration,-the blend may comprise abase-polymer such as a ,copolymer containing at least .80 percent by weight of acrylonitrile andup to 20 percent :by weight .of another :monoethylenically runsaturated monomer as recited above with from 2 to 50 percent by weight of a .copolymer containing from -10 to percent of acrylonitrile and from 30 to percent of :another monoethyleni- :cationic surface .active quaternary ammonium compound and from 5 to '2'5wpercentrofzaisubstituted :carbamyl derivative, all of which are more particularly defined hereinafter. The esters comprising an essential part of the agents of this invention are preferably long chain fatty acid partial esters of polyhydr'ic alcohols or their anhydrides, such as sorbitan monopalmitate and sorbitan monolaurate. The non-ionic surface active agents, referred to herein generally as polyethers, can be prepared by condensing a water-insoluble hydroxy-fatty acid, or esters of such acid, .or mixturexof such acid or ester, with from to 250 parts of ethylene oxide.

Among the polyhydric alcohols or anhydrides from which the partial esters may be made are those having avawoo from 2 to 8 carbon atoms, such as mannitol, sorbitol, glucose, erythritol, pentaerythritol, glycols such as ethylene glycol, triethylene glycol, propylene glycol, diethylene glycol, tetraethylene glycol, etc. Various saturated and unsaturated aliphatic acids may be reacted with the polyhydric alcohols in making the partial esters. A preferred group of partial esters are those containing a single ester linkage. However, partial esters containing more than one ester linkage may be used.

The acid used in making the partial esters may be saturated or unsaturated aliphatic acids containing from 10 to 20 carbon atoms. Preferred acids are those which are saturated or contain only one olefinic group. Examples of such acids include mono-olefinic unsaturated aliphatic acids such as 7-hexadecenoic acid, lO-undecenoic acid, l3-docosenoic acid and 9-octadecenoic acid; substituted olefinic acids, for example, such hydroxy olefinic acids as 16-hydroXy-7-hexadecenoic acid and 12-hydroxy- 9-octadecenoic acid; halogenated unsaturated acids, for example, monochloro-9-octadecenoic acid, monochloro- 12-hydroxy-9-octadecenoic acid, and halogenated acids derived by dehydration of castor oil acids followed by chlorination; saturated fatty acids such as decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, and nonadecanoic acid. These saturated acids may also have straight or branched chains, or substituted chains, and may be substituted, for example, with chlorine or other halogen atoms, as for example, monochloroctadecanoic acid, and the like.

Specific partial esters suitable for use in this invention include glyceryl monohexadecanoate, glyceryl monododecanoate, glyceryl mono-9-octadecanoate, glyceryl mono-l2-hydroxy-octadecanoate, sorbitan monododecanoate, propylene glycol mono-octadecanoate, ethylene glycol mono-octadecanoate, diethylene glycol mono-octadecanoate, and sorbitan mono-octadecanoate.

Examples of hydroxy-fatty acids which can be used as such, or in the form of partial esters with the polyhydric alcohols set forth above, for condensation with ethylene oxide to form the ether portion of the compositions of this invention, include both saturated and unsaturated hydroxy acids such as l2-hydroxy-octadecanoic acid, l2-hydroxy-dodecanoic acid, 16-hydroxy-hexadecanoic acid, ll-hydroxy-hexadecanoic acid, lO-hydroxy-octadecanoic acid, 3,12-dihydroxy-palmitic acid, 9,10,16-hydroxyhexadecanoic acid, 9,10,12,1S-hydroxy-octadecanoic acid, l6-hydroxy-7-hexadecanoic acid, 12-hydroxy-9-octadecanoic acid.

The cationic surface active agents used in this invention are the quaternary ammonium compounds having the formula:

osoirq- In the formula R1 and R0 may be the same or different and are preferably saturated aliphatic chains containing at least 6 carbon atoms; Ra, R3, R4 and R5 each represent hydrogen, or a simple alkyl or hydroxyalkyl radical of less than 5 carbons and R and R4 may further represent an acid amide chain derived from an acid and a polyamine; D1 and D2 represent oxygen, sulfur, or an imido group; the number of such groups being as g ranges from 0 to 3; g represents a whole number from 0 to 3; A represents either oxygen, sulfur, an amino group, or a simple alkyl or alkylol-substituted amino group of less than five carbons (such as NC2H4OH or NC2H5); f and j represent whole numbers from 1 to 6 preferably from 1 to 3; e and k represent whole numbers from 0 to 6, preferably from 0 to 3; m and t represent whole numbers from 1 to 6, preferably not over 2, and one of the hydrogens in each dimethylene group may be substituted by a methyl group; B represents the hydrogen of an acid or alkyl group; and X represents a negative radical such as an acyl radical or a halogen.

Substances embraced by the formula given can be obtained by condensing a saturated acid, acid ester, or acid halide with an aliphatic polyamine, reacting the condensate with a carbamyl compound, and then converting the substituted carbamyl derivatives thus obtained to its corresponding acid salt or alkylated product.

Acids which may be condensed with polyamines to obtain the condensates are the saturated acids containing at least 6 carbon atoms, such as lauric, stearic, palm oil acids, etc.

The acids may be condensed with any of the aliphatic polyamines, such as ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, hexamethylene diamine, hydroxyethyl ethylene diamine, ethyl ethylene diamine, 2,2-dimethyl-1, 3-diaminopropane, 1,3- diaminoisopropanol, beta, beta-diamino-diethyl ether and beta-beta-diamino diethyl thioether.

The carbamyl compounds which are reacted with the acid-amino condensate include urea, thiourea, guanidines, biurets, guanylureas, and diguanidines.

For the purpose of this invention, the substituted carbamyl derivatives must be converted to their acid salts or alkylated products. The acid salts are obtained by reacting the carbamyl derivatives with an acid, for example, with acetic, lactic, boric, oxalic, benzoic, salicylic, furoic, citric, tartaric; formic, phthalic, succinic, or alkyl naphthalene sulfonic acids. The alkylated products are obtained by after-treating the substituted carbonyl derivative with an alkylating agent such as ethyl chloride, benzyl chloride, ethylene oxide, ethylene chlorhydrin, or dimethyl sulfate.

The acid-amino condensates can be prepared by heating equimolal quantities of the selected saturated acid and of the polyamine at temperatures from to 200 C. until the reaction is complete as shown by the loss of one molecule of water. The mix is then cooled to 180 C. and one half mol or more of urea or other carbonyl compound is added. Ammonia is rapidly liberated as the urea becomes substituted, the temperature being maintained at between and 200 C. The product thus obtained is then reacted with the appropriate acid or with an alkylating agent to produce the compounds designated by the structural formula.

The compositions of this invention are preferably used as aqueous dispersions, and from 1 to 5 percent solids in such dispersions has been found to give most satisfactory results. The compositions can be applied to the fibers in any suitable manner, as by dipping or immersing the fiber in the medium, by spraying or dripping, by means of a wick or roller, etc.

In the conventional practice, fibers and other articles comprising the acrylonitrile polymers, copolymers and blends, are stretched in the course of their production, for orientation of the molecules and improvement in their tenacity. If the fibers are steam-stretched, after washing thereof to partially or completely remove the spinning sol- .5 vent, the anti-static medium is applied .to.the qfibers after washing. For some purposes, the heat-stretching for orientation may be dispensed with. If the fibers are not stretched in a steam atmosphere, the finishing medium may be appliedto them any time subsequent-to'their withdrawal from the spinning zone and washing thereof for removal ofthe spinning solvent and drying. Thus it may be applied to continuous filaments or to discontinuous fibers obtained by cutting or otherwise disrupting the filaments, and before or after crimping of the filaments or fibers. However, in the preferred embodiment of this invention, the finishing composition set forth above is applied to a running tow or bundle of fibers which may occur in the tower bundleincontinuous or discontinuous.

form.

The application of the compositionsof this invention are illustrated in .the following examples:

Example I An aqueous dispersion was prepared containing 2 percent solids, of which 48 percent by weight was sorbitan monopalmitate, 32 percent was the product obtained by condensing castor oil with 200 mole equivalents of ethylene oxide, percent was N-cetyl, 'N-ethyl rnorpholinium ethosulfate and 10 percent was afl-dihydroxyethyl-ot',5- di(fl-stearamidoethyl) urea acetate. This composition was applied to a tow obtained by spinning ,a blend of a first copolymer containing 97 .percentarcylonitrile and 3 percent vinyl acetate with a second copolymer containing 50 percent acrylonitrile and 50 percentv2emethyl-5 vinylpyridine. The overall 2-methyl-5-vinylpyridine content of the blend was 6 percent. Application was accomplished by immersing the tow in the dispersion. Analysis of the treated tow ,showedfrom 0.5 to 1.5 percentof the finish present, based on the tow weight. The resulting cut staple was found to be more open, softer and better lubricated than the same staple treated in a like manner with a dispersion containing 2 percent solids of which 54 percent was sorbitan monopalmitate, 36 percent was the castor oil-ethyleneoxide condensate, and 10 percent was N-cetyl, N-ethyl morpholinium ethosulfate.

Example II An aqueous dispersion was prepared containing 1.5 percent solids, of which 42 percent by weight was .sorbitan monopalrnitate, 28 percent was the :product obtained by condensing castor oil :with 200 mole equivalents of ethylene oxide, percent was -N-cetyl, N-ethyl morpholinium ethosulfate and 10 percent was onfi-dihydroxyethyl-ct,fi-di(fi-stearamidoethyl) urea acetate. This composition was applied in-the. same manner asdescribed in Example I to a tow of the same blended acrylic polymer fiber. The resulting cut=staple was found .to be more open, softer, and better lubricated, and exhibited a considerably less tendency toward the development of static electricity during textile processing, ,such as carding and drawing of the staple fibers, than did the same staple treated in a like manner with a dispersion containing 1.5 percent solids of which 54 percent was sorbitan monopalmitate, 36 percent was the castor oil-ethylene oxide condensate, and 10 percent was N-cetyl, *N-ethyl morpholinium ethosulfate.

Example Ill There was applied to a tow of the same blended acrylic polymer fiber in same manner as above an aqueous composition containing 1.5 percent solids, of which 36 percent by weight was sorbitan monopalmitate, 24 percent was the castor oil-ethylene oxide condensate prod-' I claim:

1. As a new composition .of matter, a mixture comprising from 20 percent to 50 percent by weight of a non-ionic surface active partial ester of a polyhydric alcohol and an aliphatic carboxylic acid, said alcohol having from two to 8 carbon atoms, from 15 percent to 35 percent of a non-ionic surface active ,polyether prepared by condensing from to 250 parts of ethylene oxide witha member selected from the group consisting of water-insoluble hydroxy-fatty acids, esters of such acids, and mixtures .of such acids and esters, from 10 percent to 40 percent of a cationic surface active quaternary ammonium compound having the formula:

. osonuhaving more than 10 carbon atoms, and from 5 percent to 25 percent of a substituted carbamyl compound having the formula:

wherein R1 and Rs are selected from the group consisting of saturated alkyl radicals containing at least 6 carbons; R2, R3, R4, and R5 are selected from the group consisting of hydrogen, alkyl, and hydroxyalkyl radicals containing less than 5 carbons and in which R3 and R4 may further represent an acid amide chain derived from an acid and a polyamine; D1 and D2 are selected from the group consisting of oxygen, sulfur, and imido groups, the number of such groups being as g ranges from 0 to 3; g is an integer from 0 to 3; A is selected from the group consisting of oxygen, sulfur, amino groups, alkyl-substituted amino groups containing less .than 5 carbons, and alkylol substituted amino groups containing less than 5 carbons; f andj are integers from 1 to 6; e and k are integers from 0 to 6; m and r are integers from 1 to 6; and X is a negative radical selected from the group consisting of acyl and halogen.

2. As a new composition of matter, an aqueous dispersion containing from one to 5 percent solids, said solids comprising from 20 percent to 50 percent by weight of a non-ionic surface active partial ester of a poiyhydric alcohol and an aliphatic carboxylic acid, said alcohol having from two to 8 carbon atoms, from 15 percent to 35 percent of a non-ionic surface active polyether prepared by condensing from 156 to 250 parts of ethylene oxide with a member selected from the group consisting of water-insoluble hydroxy-fatty acids, esters of such acids, and mixtures of such acids and esters, from 10 percent to 40 percent of a cationic surface active quaternary ammonium compound having the formula:

R Rl

wherein R represents an alkyl radical having less than 5 carbon atoms, R represents an alkyl radical having less than 5 carbon atoms, and R" represents an alkyl wherein R1 and Rs are selected from the group consisting of saturated alkyl radicals containing at least 6 carbons; R2, R3, R4 and R5 are selected from the group consisting of hydrogen, alkyl, and hydroxyalkyl radicals containing less than 5 carbons and in which R3 and R4 may further represent an acid amide chain derived from an acid and a polyamine; D1 and D2 are selected from the group consisting of oxygen, sulfur, and imido groups, the number of such groups being as g ranges from O to 3; g is an integer from to 3; A is selected from the group consisting of oxygen, sulfur, amino groups, alkyl-substituted amino groups containing less than 5 carbons, and alkylol substituted amino groups containing less than 5 carbons; f and i are integers from 1 to 6; e and k are integers from 0 to 6; m and t are integers from 1 to 6'; and X is a negative radical selected from the group consisting of acyl and halogen. I

3. As a new composition of matter, an aqueous dispersion containing from one to 5 percent solids, said solids comprising from percent to 50 percent by weight of sorbitan monopalrnitate, from 15 percent to 35 percent of castor oil condensed with from 150 to 250 parts of ethylene oxide, from 10 percent to 40 percent of N-cetyl, N-ethyl morpholinium ethosulfate, and from 5 percent to percent of a, B-dihydroxyethyl-a', ;8-di- (fi-steararnidoethyl) urea acetate.

4. The composition of claim 3 wherein the solids content is about one and one-half percent.

5. The method of imparting lubricity, softness and anti-static properties to shaped articles comprising an acrylonitrile polymer containing by weight in the molecule at least 80 percent of acrylonitrile which comprises applying to the article an aqueous dispersion containing from one to 5 percent solids, said solids comprising from 20 percent to 50 percent by weight of a non-ionic surface active partial ester of a polyhydric alcohol and an aliphatic carboxylic acid, said alcohol having from two to 8 carbon atoms, from 15 percent to percent of a non-ionic surface active polyether prepared by condensing from 150 to 250 parts of ethylene oxide with a member selected from the group consisting of water-insoluble hydroxy-fatty acids, esters of such acids, and esters, from 10 percent to 40 percent of a cationic surface active quaternary ammonium compound having the formula:

wherein R represents an alkyl radical having less than 5 carbon atoms, R represents an alkyl radical having less than 5 carbon atoms, and R" represents an alkyl radical having more than 10 carbon atoms, and from 5 wherein R1 and R6 are selected from the group consisting of saturated alkyl radicals containing at least 6 carbons; R2, R3, R4, and R5 are selected from the group consisting of hydrogen, alkyl and hydroxyalkyl radicals containing less than 5 carbons and in which R and R4 may further represent an acid amide chain derived from an acid and a polyamine; D and D2 are selected from the group consisting of oxygen, sulfur, and imido groups, the number of such groups being as g ranges from 0 to 3; g is an integer from 0 to 3; A is selected from the group consisting of oxygen, sulfur, amino groups, alkyl-substituted amino groups containing less than 5 carbons, and alkylol substituted amino groups containing less than 5 carbons; f and j are integers from 1 to 6; e and k are integers from 0 to 6; m and t are integers from 1 to 6; and X is a negative radical selected from the group consisting of acyl and halogen.

6. The method of imparting lubricity, softness and anti-static properties to shaped articles comprising an acrylonitrile polymer containing by weight in the molecule at least percent of acrylonitrile which comprises applying to the article an aqueous dispersion containing from one to 5 percent solids, said solids comprising from 20 percent to 50 percent by weight of sorbitan monopalmitate, from 15 percent to 35 percent of castor oil condensed with from to 250 parts of ethylene oxide, from 10 percent to 40 percent of N-cetyl, N-ethyl morpholinium ethosulfate and from 5 percent to 25 percent of a, fi-dihydroxyethyl-u, fl'-di(}3-stearamidoethyl) urea acetate.

7. A shaped article comprising an acrylonitrile polymer containing at least 80 percent acrylonitrile in the polymer molecule, said article having been treated with a finishing composition comprising an aqueous dispersion having from one to 5 percent solids, said solids comprising from 20 percent to 50 percent by weight of a nonionic surface active partial ester of a polyhydric alcohol and an aliphatic carboxylic acid, said alcohol having from two to 8 carbon atoms, from 15 percent to 35 percent of a non-ionic surface active polyether prepared by condensing from 150 to 250 parts of ethylene oxide with a member selected from the group consisting of water-insoluble hydroxy-fatty acids, esters of such acids, and mixtures of such acids and esters, and from 10 percent to 40 percent of a cationic surface active quaternary ammonium compound having the formula:

wherein R represents an alkyl radical having less than 5 carbon atoms, R represents an alkyl radical having less than 5 carbon atoms, and R" represents an alkyl radical having more than 10 carbon atoms, and from 5 percent wherein R1 and R6 are selected from the group consisting of saturated alkyl radicals containing at least 6 carbons; R2, R3, R4, and R5 are selected from the group consisting of hydrogen, alkyl, and hydroxyalkyl radicals containing less than 5 carbons and in which R3 and R4, may further represent an acid amide chain derived from an acid and a polyamine; D1 and D2 are selected from the group consisting of oxygen, sulfur, and imido groups, the number of such groups being as g ranges from to 3; g is an integer from 0 to 3; A is selected from the group consisting of oxygen, sulfur, amino groups, alkyl-substituted amino groups containing less than 5 carbons, and alkylol substituted amino groups containing less than 5 carbons; f and j are integers from 1 to 6; e and k are integers from 0 to 6; m and tare integers from 1 to 6; and X is a negative radical selected from the group consisting of acyl and halogen.

8. An acrylonitn'le polymer in fiber form, said fiber having been treated with an aqueous dispersion containing from one to 5 percent solids, said solids comprising from 20 percent to 50 percent by weight of sorbitan monopalmitate, from 15 percent to percent of castor oil condensed with from 150 to 250 parts of ethylene oxide, from 10 percent to 40 percent of N-cetyl, N-ethyl morpholinium ethosulfate and from 5 percent to 25 percent of a, fl-dihydroxyethyl-a',fi-di(p-stearamidoethyl) urea acetate.

9. An acrylonitrile polymer in fiber form, said fibers having deposited at least on the'outer surfaces thereof a conditioning agent comprising a mixture of 20 percent to percent by weight of sorbitan monopalmitate, from 15 percent to 35 percent of castor oil condensed with from to 250 parts of ethylene oxide, from 10 percent to 40 percent of N-cetyl, N-ethyl morpholinium ethosulfate and from 5 percent to 25 percent of a, B-dihydroxyethyl-a', ;8'-di(,8-stearamidoethyl) urea acetate.

References Cited in the file of this patent UNITED STATES PATENTS 2,212,369 Jaeger Aug. 20, 1940 2,293,826 Iselin et al Aug. 25, 1942 2,304,113 Morgan et a1. Dec. 8, 1942 2,686,137 Rossin et a] Aug. 10, 1954

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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2837446 *Jun 11, 1956Jun 3, 1958Monsanto ChemicalsTextile materials with an anti-static finish and process of making same
US3044874 *Feb 19, 1959Jul 17, 1962Gen Aniline & Film CorpPhotographic materials
US3155455 *Dec 12, 1960Nov 3, 1964Phillips Petroleum CoRemoval of vanadium from aqueous solutions
US3395107 *Jul 6, 1964Jul 30, 1968Burnthall Edward VernonAntistatic composition for synthetic fibers
US3627723 *Dec 26, 1968Dec 14, 1971Du PontFiller loaded elastomeric compositions having improved extrudability and physical properties
US4022938 *Jan 23, 1975May 10, 1977The Procter & Gamble CompanyFabric treatment compositions
US4103047 *Sep 3, 1976Jul 25, 1978The Procter & Gamble CompanyFabric treatment compositions
US4110498 *Mar 8, 1976Aug 29, 1978The Procter & Gamble CompanyFabric treatment compositions
US4124543 *Mar 6, 1978Nov 7, 1978Kao Soap CompanyAnti-static agent composition
US4128484 *Jul 14, 1975Dec 5, 1978The Procter & Gamble CompanyFabric softening compositions
US5941620 *May 5, 1997Aug 24, 1999Peka-Metall AgCorner furnishing unit
DE1132536B *Jan 15, 1959Jul 5, 1962Boehme Fettchemie GmbhVerfahren zur Verhuetung der elektrostatischen Aufladung von Materialien, insbesondere Textilien
DE2516104A1 *Apr 12, 1975Oct 30, 1975Procter & GambleTextilbehandlungszusammensetzungen
DE2631114A1 *Jul 10, 1976Feb 10, 1977Procter & GambleGewebeweichmacher
Classifications
U.S. Classification428/394, 260/DIG.200, 252/8.84
International ClassificationD06M13/432, D06M15/53, D06M13/165, D06M13/405, D06M23/00, D06M13/477, D06M13/224
Cooperative ClassificationD06M2101/28, D06M13/432, Y10S260/20, D06M13/165, D06M23/00, D06M13/224, D06M13/477, D06M15/53, D06M13/405
European ClassificationD06M13/224, D06M13/405, D06M13/477, D06M15/53, D06M13/432, D06M23/00, D06M13/165