US2286794A - Yarn conditioning process and composition therefor - Google Patents

Yarn conditioning process and composition therefor Download PDF

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US2286794A
US2286794A US36045140A US2286794A US 2286794 A US2286794 A US 2286794A US 36045140 A US36045140 A US 36045140A US 2286794 A US2286794 A US 2286794A
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parts
salt
cellulose
yarns
yarn
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Joseph B Dickey
James G Mcnally
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Eastman Kodak Co
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Eastman Kodak Co
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/48Phosphonous acids R—P(OH)2; Thiophosphonous acids including RHP(=O)(OH); Derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/38Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/38Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/3804Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
    • C07F9/3839Polyphosphonic acids
    • 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
    • Y10T428/2965Cellulosic

Description

Patent ed June 16, 1942 UNITED sTATEs PATENT YARN CONDITIONING PROCESS AND COMPOSITION THEREFOR Joseph B. Dickey and James G. McNaiiy, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, Jersey N. Y., a corporation of New No Drawing. Applicationoctoberii, 1940,

' Serial No. 360,451

is claims. (oi. 252-434;)

This invention relates to the'treatment of cellulose organic derivative filamentsQfibers, threads and the like and more particularly to a method of eliminating the tendency of such materials to accumulate charges of static electricityin twisting, winding and spinning. The invention also relates particularly to the treatment of cellulose organic'derivative cut staple fibers to adapt them for the manufacture of spun yarns. As is well known, cellulose crganic derivative materials, particularly in filament,-yarn, or sheet form, are particularly subject to the accumulation on their surfaces of charges of static electricity from frictional and other influences. In the case of filaments and yarns in which the surface area of the material (per unit of weight) is enormously greater as compared to sheets or films,

or eliminate the tendency. of such yarns to accumulate chargesof electricity under frictional and other influences. A further object is to provide a method of facilitating the handling and employment of ce11ul0se organic" derivative cut staple fibers in the various-operationsinvolved in the manufacture of spun yarns; A still fur- I ther. object is to provide amethod fof'treating in the utilization of cut staple, as forexample, in the making of spun yarn, since in carding and combing considerable friction is developed and. as a result sufiicient charges accumulate on the fibers to make the formation of the web diiiicult,

if not impossible; furthermore, even if a webis formed with some degree of success, the subsequent drafting operation produces a very uneven spun yarn'or intermediate roving due to the Y presence of the static charge.

In addition, there is the ever-present fire hazard.

Cellulose derivative yarn, particularly in the form of cut staple, is extremely difiicult to handle in the various operations involved in making spun yarn, not only because such material is composed of filaments having smooth, glass-like surfaces without natural kink or irregularity, but also because it has relatively negligible moisture content at normal humidities, ascompared tonat ural fibers such aslcotton and wool, making it inherently far more susceptible to the accumulation of static. Thecharges accumulating on cellulose derivative cut staple fibers are, under some circumstances, .even sufficient ,to :separate the individual fibers a distance of inches, notwithstanding their relatively minute size.

This invention has as-its principal object to provide an improved method forthe treatment of cellulose organic derivative yarns to reduce celluloseorganic derivative yarns in either filament .orcut staple form, wherein the material is simultaneously softened and lubricated and. .the accumulation of-iHstaticcharges I thereon is prevented, Another object is toprovide an improved, typeflof celluloseorganic derivative cut staple having little or no tendency toward accumulation -ofstatic \electrical' charges.

objects will appear hereinafter. I

These objects are accomplished bythe following inventionv which in its broader aspects c'omprises applying to cellulose organicvderivative yarns either in the form of filaments-threads.

or stable fibers, an antistatic'composition char:

acterized by the presence thereinof a salt of an I acid of phosphorus selected-fromthe group consisting of the phosphonicand :phosphinic aclds. T

The compounds froinwhich these salts" are prepared may be said to have the following structural formula:

I OH loriinore on v (i g OH lormore I I OH lormore wherein R. is an alkyl group. ".The .phosphonic and phosphinic acids and their preparation have been described in general in U. S. Patent 2,137,792. In preparing/salts the/acids are reacted with one or two equivalents of any desired organic 'or inorganic base. v I In accoTdancewith our invention theab'ovementioned salts may be a'pplied'to the yam' in any convenient manner, for example, by roll, wick, immersion, spraying or the like. Inasmuch as these compounds are soluble in oil they may be dissolved or dispersed in oils such as mineral oil, blown and unblown', drying, and semi-drying,

vegetable and animal oils, examples of which are light mineral, neats-foot, olive, teaseed, castor,

bF I

Other v v Hydrocarbon mixturo- P I .Dimethylcyclohexylamine ru) ll soya bean, rapeseed oils, etc., and other lubricants. I

In the following examples and description, we have set forth several of .the preferred embodiments of our invention, butthey are included merely for purposes of illustration and not as a limitation thereof.

Example 1 c "H P is applied to textile fibers or threads by means of a bath, wick, roller, spray, etc. to facilitate their knitting, weaving, spinning and the like. Yarns lubricated (1-25%) with compoundsof this type are of special value in the preparation of cut staple fibers. These fibers may be oiled before or after cutting. I

' A conditioning liquid is made up as follows: 7d parts glycerol acetone butyrate a i 30 parts diethylcyclohexylamine salt of the phosphonic, acids derived from gas oil or lubricating oil fractions I Gas oil 5r lub oil fraction-P-OH I Y a v 1 .Diethylcyclohexylamlne) and applied to textile materials (silk, wool, cotton, viscose, cellulose derivatives, etc.)' as in Example 1. If the yarn is intended primarily for knitting, .the amountof conditioning liquid applied'may ,vary from 4-25% by weight of the yarn and if for weaving, between 1-5% by weight of the yarn.

Cellulose acetate filaments treated *as described above are quite soft and pliable and give improved results 'in -various textile operations such as'weavingyknitting, eta/and especially in the production of cut staple fibers.

Conditioning liquids particularly useful for the treatment of various types of yarns in ac-' cordance with our invention particularly those composed of or containing cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, and similar organic acid esters, and especially adapted for the deelectrification or anti-static treatment of cellulose organic derivative cut staple yarns are as follows:

- Example 3 40 parts olive oil a 1-10 parts dimethylcyclohexylamine salt from the phosphonates from a mixture of Co to C12 hydrocarbons I n, 59-50 parts ethanolaniinepropionatebutyrate Q I Q Example 4 I 140 parts cyclohexanephosphonate triarnylamine salt- 99-9o parts blown olive oil .Diethanolamine) 97-88 parts sperm Example 5 1-5 parts hexylbenzene diphosphonate sodiumtriethanolamine salt Co n-P ll\ 0 ONa a P .Triethanolamme salt ll\ 2 parts sodium sulfate 92-78 parts neats foot oil 5-15 parts naphthenic acid Example 6 l lqparts naphthene phosphonate ditetrahydrofurfurylamine salt 0H NaphthenePP .Ditetrahydroiuriurylamlnc) 0 oil l 79-50 parts 1 blown neat's-foot' oil- 20-40 parts tetrahydrofurfuryl formal (Beta-hydroxy-beta-phosphonic' heptane phos- Dhinic acid cyclohexylamine salt) l I I ExampleQ ;89-70 parts blown sperm oil 10-20 parts oleic acid 1- 10 parts r on CH -C5Hw-P Diethylcyclohexylamme salt o= OH 0 on ,(Beta-hydroxy-beta-phosphonic hexane phosphinic acid diethylcyclohexylamine salt) 7 Example 10 5 parts (benzyl'trimethyl ammoniumhydroxide salt ofthe alkyl phosphonic acid of polymeric hydrocarbons from cracked gasoline) OH I v 'Alkyl-P @cnfiuonm (long chain)ll\ (Structure 0 0H 0H 7 Own) parts blown olive oil 1 r 20 parts blown neats-foot oil a 20 parts tetrahydrofurfuryl formal 1 Example 11 5 parts be'nzylphosphinate furiurylamine salt 3 parts glycerol '75 parts olive oil Example 12 5 parts water soluble cellulose ester 85 parts water -5 parts octyl phosphonate timeroa am.) 5 parts sulfonated castor oil 7" i v I Examplew 85 parts water 10 parts gelatin -'5 parts oleyl phosphonate triethanolamine salt Example 14 99430. parts light mineral 11 a l-lO parts octylphosphonate dib'utylcyclohexylamine salt a (CsHnfiqOH Dibutylcyclobexylamine) v Example 15 g I 99-90 parts butyl stearate 1-10 parts mixed hydrocarbon (6-12) phosphonate diethylcyclohexyiamlne salt (Mixed hydrocarbons C C P-OH F 1,) Diethylcyclrihexylamine) O OH 1 V Example 16 In a 20% acetone solution of cellulose acetate I is dissolved 1-5% by weight'o'f benzyl trimethylammonium hydroxide salt of the alkyl phosphonic acid of polymeric hydrocarbons from cracked gasoline. The acetone solution is then extruded into an evaporative atmosphere and the filaments thus produced are wound, or twisted and wound. If desired. the filaments. produced by this method are oiled with any 'oijthe combinations of lubricants orlubricantsplus condiethyltetrahydro- OCHr-,P .Diethyltetrahydroluriurylamino s t a 15 parts 'sulfonated castor oil, '2parts water v invention may be a'pplied by a wide variety of methods. Forexample', we may employ the agent as an ingredient of the spinning dope from which the filaments are formed, the amount *of the agentsiso employed "depending'upon a number of (factors, such as'theparticular cellulose deriva- 'tive'. used inmaking the yarn; the solvent or solvent combination"*usedxdn making up the spinning "solution, and the "properties desired in the finished yarn, etc.

- If the conditioning' agentis to be applied to y the yarn after spinning,""this'may be done-by bringing the yarn in contabtWith a wick; roll, or felt wet therewith,=or the liquldmay be" applied by immersion, spray, or otherwise. The

particular point at which the liquid-isapplied may vary. It may,=- for" example, be" applie'd 'to the yarn insideor outside thespinnin'g cabinet, between the guide and godet rollybetw'een the 'godot or-other roll-"orguide and the point of winding and/or'twisting." ;'In some cases, "the liquid may even be applied to the yarnyafter winding onto cones, spools, bobbins, or; the like or .by the so-called b'obbinto bobbin method. In the case of staple fiber manufacture, the liquid may be applied to the yarn prior to, or after ditioning agents previously described, Filaments thus prepared are of particular value in the preparation of cut stapleflbers.

Any of the above compositions may be applied to the yarn intended for useln circular knitting by means oi a bath, wick, spray, roller, pad or v any suitablemeans.

I The amount 'of conditioning liquid applied may vary between 525% by weight of the yarn. Usually, however, the

amount of conditioning liquid applied is about 10-15 by weight of the yarn. Yarn composed of cellulose acetate conditioned as described above gives excellent results when used in the circular knitting process.

As will be apparent from the above examples and description the conditioning agents of our natural orartificialmaterials. I The term "yarn. as used hereinan'd in the cutting into staple lengths.

The amount of the agent so employed will vary ferred primarily toyarn treating compositions,

containing'only the conditioning agent and an oil, other ingredients such as solvents, nonsolvents,- emulsifying agents, blending agents I and the like, may be added within the scope of our invention. Likewise, various 'dyesorother coloring matter may be. included inLcaseit is desired to permanently or fugitively tint or dye the materialundergoingtreatment. Q Although'we have it convenient to'-'illustrate our invention by reference to compositions'containing specific percentages-of the various ingradients, these percentages may vary widely depending upon the particular-purposefor which the composition is intended. For example, hit I is desired to control the deelectrifying action of the conditioning'agent, the amount of the agent maybe adjusted as, for example, by reducing the-amountof the agent and correspondingly increasing the amount of oil or other ingredient. 7

While we have described our'invention' with particular reference to the treatment 'ofya'rn's composed of organic derivatives of cellulose such as cellulose acetate, theconditioning agents'and formulas described hereinare applicable to the conditioning ofv many other typesof cellulose derivative yarns such" as those composed of or containing. ecellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose I acetate butyrate, ethyl cellulose, methyl cellulose,

benzyl cellulose and others, as well as to the conditioning of silk, wool, cotton, viscose "and other claims is to be understood as-including a single scour baths.

the form of a thread, either of high or'low twist, single or multiple. threads associated or twisted together, composite threads composed of a mixture of natural andartificial .filaments- 1 or a composite thread formed by twisting to- "getherindividual strands of natural or artificial materials, as well as cut staple fibers produced from natural and/or artificial filaments vor threadsg and spun yarn produced from such staple fibers. I, As indicated above, the yarn conditioning agents of our invention are exceptionally good solvents for a wide variety. of mineral,;blown and unblown, drying and semi-drying animal 5 and vegetable oils such as cottonseed, olive, castor,

neat's-foot, sperm and other oils. This enables them to be used with any of such oils in making up a variety of yarn treating formulas of vary ing composition.

s The yarn conditioning method and compositions of our invention possess many outstanding advantages. The fundamental and outstanding characteristic of the agents employed inlaccord ance with the invention-is their ability to deelectrifyyarns, especially those composed of or confilament, a plurality of filaments associated into prises applying thereto a composition containing as its essential anti-static component a salt of an acid of phosphorus selected from the group consisting of the alkyl phosphonic and phosphinic acids in which the alpha carbon atom of the alkyl group is devoid of hydroxyl groups.

3. The method of eliminating the tendency of yarns, filaments or fibers composed of or containing cellulose acetate to accumulate charges of static electricity, which comprises applying thereto a composition containing as its essential anti-static component a salt of an, acid of phosphorus selected from the group consisting or the alkyl phosphonic and phosphinic acids in which the alpha carbon atom of the alkyl. group is devoid of hydroxyl groups.

4. The method of eliminating the tendency of yarns, filaments or fibers composed of or containing organic derivatives of cellulose, to accumulate charges of static electricity, which comprises applying thereto a composition containing as its essential anti-static component diethylcycloh'exylamine salt of the alkyl phosphonic taining organic derivatives ofcellulose such as cellulose acetate and render them amenable to various textile operations, especially operations such as those involved in the manufacture of out Another outstandingcharacteristic of these compoundsis their exceptional solvent power for a wide variety of -mineral, animal, and ;vegetable oils and their ability to act as lubricating assiststaple fibers, as well as in weaving and knitting.

antsin conjunction with these oils when applied these hydrocarbons cannot be identified by reference to any specific formula, since a large number of .compounds are present in anypetroleum or gas oilfraction. Ingeneral, however, it may be said'that such hydrocarbons can be regarded to contain at least six carbon-atoms and which may contain one or more double bonds; Ofthese dialkyl cyclohexylamine salts we have found as of particular value the diethyl cyclohexylamine salt of the alkyl phosphonic acids derived from such hydrocarbons, the dimethyl cyclohexylaminesalt obtained from the phosphonates from a mixture of Ce-Ci: hydrocarbons and the benzyl trimethyl ammonium hydroxide salt of the alkyl phosphonic acid of polymeric, hydrocarbons from cracked gasoline.

What we claim and desire "to secure by Letters Patent of the United States is: 1

1. The method of eliminatingfthetendency of yarns, filaments or fibers to accumulate'charges of static electricity, which comprises applying thereto a compositioncontaining as its essential anti-static, component a salt of an acid of phosphorus selected from the group consisting of the acids derived from gas oil or lubricating oil fractions;

, 5. The methodo! eilminating the tendency of I yarns, filaments or fibers composed of or containing organic derivatives of cellulose to accumulate charges of static electricity, which comprises applying thereto a composition containing as its essential anti-static component dimethylcyclohexylamine salt from the phosphonates from a mixture 01' Co to C1: hydrocarbons.

6. The method of eliminating the tendency of yarns, filaments or fibers composed of or containingorganic derivatives of cellulose to accumulate charges-oi static electricity, which comprises applying thereto a composition containing as its essential anti-static component benzyl trimethyl ammonium hydroxide salt of the alkyl phosphonic acid of polymeric hydrocarbons from cracked gasoline. i

'7. A composition adapted, when applied to textile yarns, filaments or fibers to eliminate the tendency of such materials to accumulatecharges of static electricity, said composition containing as its essential anti-static component a salt of an acid otphosphorus selected from the group consisting of the alkyl phosphonic and phosphinic acids in which thealpha'carbon atom of the alkyl group is devoid of hydroxyl groups.

8. A composition adapted, when applied to cellulose organic derivative yarns, filaments or fibers, to eliminate the tendency'of such materials to accumulate charges of static electricity, said composition containing as its essential antistatic component a salt of an acid of phosphorus selected from the group consisting of the alkyl phosphonic and phosphinic acids in which the alpha carbon atom of the alkyl group is devoid of hydroxyl groups.

9. A composition adapted, whenapplied to cellulose acetate yarns, filaments or fibers to eliminate thetendency of such materials to accumulate chargesof static electricity, said composition containing as its essential anti-static component a 'saltoi an acid of phosphorus selected ,irom the group consisting or the alkyl phosphonic and phosphinic acids in which the alpha carbon atom of the alkyl group is devoid of hydroxyl groups.

10. A composition adapted, when applied to rials to accumulate charges of static electricity,

. said composition containing as its essential antiasseycc static component diethylcyclohexylamine salt of the alkyl phosphonic acids derived from gas oil I or lubricating oil fractions.

11. A composition adapted, when applied to cellulose organic derivative yarns, filaments or fibers, liq-eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its essential antistatic component dimethylcyclohexylamine salt from the phosphonates from a mixture of Ca to C12 hydrocarbons.

12. A composition adapted, when applied 'to cellulose organic derivative yarns, filaments, or fibers, to eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its essential antistatic component benzyl trimethyl ammonium hydroxide salt of the alkyl phosphonic acid of polymeric hydrocarbons from cracked gasoline.

13. Textile yarns having a lessened tendency to accumulate charges of static electricity, said yarns containing a salt of an acid of phosphorus selected from the group consisting of the alkyl phosphonic and phospinic acids in which the alpha carbon atom of the alkyl group is devoid of hydroxyl groups.

14. Textile yarns composed of or containing organic derivatives of cellulose having a lessened tendency to accumulate charges of static elec-.

tricity, said yarns containing a salt of an acid of phosphorus selected from the group consisting of the alkyl phosphonic and phosphinic acids in is devoid of hydroxyl groups.

l5. Textile yarns composed of or containing cellulose acetate having a lessened tendency to l6. Textileyarns'composed of or containing or ganic derivatives of cellulose having alessened tendency to accumulate charges of static electricity, said yarns containing diethylcyclohexylamine salt of the alkyl phosphonic acids derived from gas oil or lubricating oil fractions.

17. Textile yarns composed of or containingorganic derivatives of cellulose having a lessened tendency to accumulate charges or static electricity, said yarns containing dimethylcyclohexylamine salt from the phosphonatesfrom a mixture of C6 to C12 hydrocarbons.

18. Textile yarns composed of or containing organic derivatives of cellulose having a lessened tendency to accumulate charges of static. electricity, said yarns containing benzyl trimethyl ammonium hydroxide salt of the alkyl phosphonic acid of polymeric hydrocarbons from,

cracked gasoline.

JOFSEPH B. D'ICKEY. JAMES G. MGNALLY.

which the alpha carbon atom of the alkyl group

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2460043A (en) * 1945-08-29 1949-01-25 Allied Chem & Dye Corp Phosphonic acid esters
US2471472A (en) * 1945-04-28 1949-05-31 Victor Chemical Works Method of forming phosphonic and thiophosphonic acid chlorides
US2484146A (en) * 1945-04-07 1949-10-11 Houghton & Co E F Lubricating composition
US2486657A (en) * 1945-04-28 1949-11-01 Monsanto Chemicals Diolefin phosphonic acids and polymers thereof
DE975308C (en) * 1953-12-21 1961-11-02 Boehme Fettchemie Gmbh Antistatic making finished textile fabrics or knitted fabrics made of fully synthetic fiber material
US3206290A (en) * 1961-01-16 1965-09-14 Exxon Research Engineering Co Organic ammonium phytates as additives for promoting electrical conductivity
US3346487A (en) * 1965-06-11 1967-10-10 Monsanto Co Deflocculation of solid materials in aqueous medium
US3348613A (en) * 1965-05-19 1967-10-24 Monsanto Co Novel acidizing composition and method
US3366678A (en) * 1963-08-21 1968-01-30 Armour & Co Para xylylene bis(phosphonous acid) bis (anilino) compounds useful as anti-bacterialagents
US3397219A (en) * 1963-03-29 1968-08-13 British Petroleum Co Preparation of phosphorus-containing olefin polymers and salts thereof
US3422021A (en) * 1963-03-18 1969-01-14 Procter & Gamble Detergent composition
US3432547A (en) * 1963-08-21 1969-03-11 Armour & Co Bis-aminophosphinic acids useful as anti-bacterial agents
US3609075A (en) * 1968-06-25 1971-09-28 Procter & Gamble Cleaning and softening detergent compositions
US3663274A (en) * 1970-06-03 1972-05-16 Us Navy Method of minimizing accumulation of electrostatic charge on polyethylene
US4118327A (en) * 1977-03-28 1978-10-03 Colgate Palmolive Company Fabric softener and anti-static compositions
FR2399433A1 (en) * 1977-08-01 1979-03-02 Ciba Geigy Ag Salts of quaternary ammonium antistatic agents or softeners touch presenting fatty acid radicals, their process for the preparation and use
FR2416252A1 (en) * 1978-02-06 1979-08-31 Ciba Geigy Ag Process for the flame retardancy of an organic fibrous material with phosphonic acid salts
US4292182A (en) * 1978-10-30 1981-09-29 Badische Corporation Imparting anti-soiling properties to fibers
US4632767A (en) * 1985-06-14 1986-12-30 Takemoto Yushi Kabushiki Kaisha Antistatic agents for synthetic fibers

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2484146A (en) * 1945-04-07 1949-10-11 Houghton & Co E F Lubricating composition
US2471472A (en) * 1945-04-28 1949-05-31 Victor Chemical Works Method of forming phosphonic and thiophosphonic acid chlorides
US2486657A (en) * 1945-04-28 1949-11-01 Monsanto Chemicals Diolefin phosphonic acids and polymers thereof
US2460043A (en) * 1945-08-29 1949-01-25 Allied Chem & Dye Corp Phosphonic acid esters
DE975308C (en) * 1953-12-21 1961-11-02 Boehme Fettchemie Gmbh Antistatic making finished textile fabrics or knitted fabrics made of fully synthetic fiber material
US3206290A (en) * 1961-01-16 1965-09-14 Exxon Research Engineering Co Organic ammonium phytates as additives for promoting electrical conductivity
US3422021A (en) * 1963-03-18 1969-01-14 Procter & Gamble Detergent composition
US3397219A (en) * 1963-03-29 1968-08-13 British Petroleum Co Preparation of phosphorus-containing olefin polymers and salts thereof
US3366678A (en) * 1963-08-21 1968-01-30 Armour & Co Para xylylene bis(phosphonous acid) bis (anilino) compounds useful as anti-bacterialagents
US3432547A (en) * 1963-08-21 1969-03-11 Armour & Co Bis-aminophosphinic acids useful as anti-bacterial agents
US3348613A (en) * 1965-05-19 1967-10-24 Monsanto Co Novel acidizing composition and method
US3346487A (en) * 1965-06-11 1967-10-10 Monsanto Co Deflocculation of solid materials in aqueous medium
US3609075A (en) * 1968-06-25 1971-09-28 Procter & Gamble Cleaning and softening detergent compositions
US3663274A (en) * 1970-06-03 1972-05-16 Us Navy Method of minimizing accumulation of electrostatic charge on polyethylene
US4118327A (en) * 1977-03-28 1978-10-03 Colgate Palmolive Company Fabric softener and anti-static compositions
FR2399433A1 (en) * 1977-08-01 1979-03-02 Ciba Geigy Ag Salts of quaternary ammonium antistatic agents or softeners touch presenting fatty acid radicals, their process for the preparation and use
US4264516A (en) * 1977-08-01 1981-04-28 Ciba-Geigy Corporation Quaternary ammonium salts of antistatic agents or softening agents containing fatty acid radicals, process for the production and use thereof
FR2416252A1 (en) * 1978-02-06 1979-08-31 Ciba Geigy Ag Process for the flame retardancy of an organic fibrous material with phosphonic acid salts
US4292182A (en) * 1978-10-30 1981-09-29 Badische Corporation Imparting anti-soiling properties to fibers
US4632767A (en) * 1985-06-14 1986-12-30 Takemoto Yushi Kabushiki Kaisha Antistatic agents for synthetic fibers

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