US3329758A - Treating polyester filament with a surface active compound to permit lagging before drawing - Google Patents

Treating polyester filament with a surface active compound to permit lagging before drawing Download PDF

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Publication number
US3329758A
US3329758A US288522A US28852263A US3329758A US 3329758 A US3329758 A US 3329758A US 288522 A US288522 A US 288522A US 28852263 A US28852263 A US 28852263A US 3329758 A US3329758 A US 3329758A
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Prior art keywords
filaments
glycol
acid
employed
percent
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US288522A
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English (en)
Inventor
Jr Herbert S Morgan
Jr Horace M Robinson
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Monsanto Co
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Monsanto Co
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Priority to NL133640D priority Critical patent/NL133640C/xx
Application filed by Monsanto Co filed Critical Monsanto Co
Priority to US288522A priority patent/US3329758A/en
Priority to GB24165/64A priority patent/GB1022035A/en
Priority to LU46326D priority patent/LU46326A1/xx
Priority to CH778464A priority patent/CH440538A/fr
Priority to DE19641494670 priority patent/DE1494670B2/de
Priority to SE7343/64A priority patent/SE304349B/xx
Priority to DK302964AA priority patent/DK113309B/da
Priority to FR978502A priority patent/FR1398690A/fr
Priority to NL6406827A priority patent/NL6406827A/xx
Priority to BE649400A priority patent/BE649400A/xx
Application granted granted Critical
Publication of US3329758A publication Critical patent/US3329758A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/32—Polyesters
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

  • This invention relates to an improved method for producing articles prepared from high molecular weight synthetic linearpolyesters. More particularly, it relates to an improved method for improving the surface characteristics of articles prepared from synthetic linear polyesters.
  • a common procedure is to employ two filament advancing devices generally known as a feed roll and draw roll. Filament stretching is achieved by running these rolls at differential speeds with the amount of stretching or drawing being determined by the ratio of the peripheral speeds of the two rolls.
  • a braking device is sometimes placed between the feed roll and draw roll.
  • the braking device consists of a pin, called the draw pin, around which the yarn is wrapped a number of times.
  • the draw pin introduces frictional drag 0n the moving filaments which causes stretching to take place in the area of the draw pin.
  • the introduction of frictional drag to localize stretching is utilized in those instances where there is a tendency for non-uniform drawing to occur since greater uniformity can be obtained by employing this procedure.
  • the heating may be carried out by inserting a hot pin, a hot plate, or hot fluid bath between the feed roll and draw rolls of the drawing apparatus or by using a heated feed roll. Elevated temperatures are effective because intermolecular forces are diminished by the resulting increase in molecular activity, and therefore the ratio of the force required to draw the yarn to that required to break it is lessened. Permissible temperatures which may be used in hot drawing vary somewhat with the nature of the polymer from which the yarn is formed, since the maxium temperature which can be employed is limited by the polymer sticking point. It is a common practice to employ a hot drawing technique when processing yarn for use in products which require great tensile strength, as for example in the manufacture of reinforcement cords for inflatable tires.
  • the pricipal cause of filament break-age while drawing is the buildup of excessive tension of the yarn which in turn is intensified, for the most part, by inter-filament friction and by the generation of excessive friction as the yarn passes over the draw pin when such device is employed.
  • aqueous emulsion the solids content of which comprises a cationic surface active quaternary ammonium compound, prior to the drawing step. It has further been found that this procedure not only facilitates the drawing operation, but that, in addition thereto, substantial advantages are imparted to the ultimate yarn product.
  • a finish formulation as described above, has been found to maintain improved drawing properties and stability to heat in a high molecular weight synthetic linear polyester yarn after a lag time of about 30 days.
  • the cationic surface active agents used in this invention are the quaternary ammonium compounds having the formula wherein R represents an alkyl radical having more than 10 carbon atoms and R represents an alkyl radical having less than carbon atoms.
  • Examples of such quaternary ammonium compounds represented by the above formula include soya dimethyl ethyl ammonium ethosulfate, in which the alkyl groups represented by R are derived from the fats contained in the soya oil, consisting chiefly of saturated 16 and 18 carbon aliphatic carboxylic acids as their esters, lauryl dimethyl ethyl ammonium methosulfate, myristyl dimethyl ethyl ammonium ethosulfate, palmityl dimethyl ethyl ammonium propiosulfate, margaryl dimethyl ethyl ammonium butyrosulfate, stearyl dimethyl ethyl ammonium ethosulfate, oleyl dimetyl
  • the synthetic linear condensation polyesters contemplated in the practice of this invention are those formed from dicarboxylic acids and glycols, and copolyesters or modifications of these polyesters and copolyesters. In a highly polymerized condition, these polyesters and copolyesters can be formed into filaments and the like.
  • polyesters and copolyesters specifically useful in the instant invention are those resulting from heating one or more of the glycols of the series HO(CH OH, is which n is an integer from 2 to 10, with one or more dicarboxylic acids or ester-forming derivatives thereof.
  • dicarboxylic acids and ester-forming derivatives thereof useful in the present invention are terephthalic acid, isophthalic acid, sebacic acid, adipic acid, p-carboxyphenoacetic acid, succinic acid, p,p-dicarboxybiphenol, p,p-dicarboxycarbanilide, p,p'-dicarboxythiocarbanalide, p,p-dicarboxydiphenylsulfone, p-carboxyphenoxyacetic acid, p-carboxyphenoxypropionic acid, p-carboxyphenoxybutyric acid, p-carboxyphenoxyvaleric acid, p-carboxyphenoxyhexanoic acid, p-carboxyphenoxyheptanoic acid, p,p'-dicarboxydiphenylmethane, p,p'-dicarboxydiphenylethane, p,p-dicarboxydiphenyl
  • n is an integer from 1 to 4, and the aliphatic and cycloaliphatic aryl esters and half esters, ammonium and amine salts, and the acid halides of the above-named compounds and the like.
  • glycols which may be employed in practicing the instant invention are ethylene glycol, trimethylene glycol, tetramethylene glycol, decamethylene glycol, and the like.
  • Polyethylene terephthalate is preferred because of the ready availability of terephthalic acid and ethylene glycol, from which it is made. It also has a relatively high melting point of about 250 through 255 C. and this property is particularly desirable in the manufacture of filaments in the textile industry.
  • modified polyesters and copolyesters which are useful in the practice of the present invention are those polyesters mentioned above modified with dialkylesters of saturated essentially linear aliphatic dicarboxylic acids containing 20 carbon atoms having the general formula wherein R and R are alkyl radicals containing from 1 to 10 carbon atoms and more preferably are alkyl hydrocarbon radicals containing from 1 to 5 carbon atoms including methyl, ethyl propyl, isopropyl, n-butyl, sec.
  • A is a linear saturated aliphatic radical containing from 14 to 18 carbon atoms in its chain; n is an integer of either 1 or 2; and y is an integer from 0 to 2.
  • the total number of carbon atoms in A and the side chains thereof is 18.
  • R and R may be the same or may be difierent alkyl radicals.
  • dialkyl esters found useful in this invention include dialkyl 1,20-eicosane dioate, dialkyl S-ethyl octadecane-l, l8-dioate, dialkyl dimethyl octadecane-1,18- dioate, dialkyl diethylhexadecane-l,l6-dioate and the like, where the dialkyl groups are methyl, ethyl, propyl, and the like including alkyl hydrocarbon radicals containing from 1 to 5 carbon atoms. Mixtures of any of the materials described above may also be used.
  • mixtures of above 20 to weight percent of dimethyl l, 20-eicosane dioate and about 80 to 20 weight percent of dimethyl 8-ethyl octadecane-1,18-dioate are quite useful.
  • the amounts of necessary reactants employed to make the modified polyesters, on a molar basis, are ordinarily one mole equivalent of a mixture of the two types of dialkyl esters of aromatic and C dicarboxylic acids and a molar excess of the glycol.
  • the dialkyl aromatic dicarboxylic acid esters are present in amounts from about 65 to weight percent and the dialkyl ester of the aliphatic C dicarboxylic acid is present in amounts from about 35 to about 5 weight percent.
  • modified polyesters and copolyesters which are useful in the practice of the present invention are the polyesters and copolyesters mentioned above modified with chain terminating groups having hydrophilic properties, such as the monofunctional ester-forming polyesters bearing the general formula wherein R is an alkyl group containing 1 to 18 carbon atoms or an aryl group containing 6 to 10 carbon atoms, and m and n are integers from 2 to 22, and x is a whole number indicative of the degree of polymerization, that is, x is an integer from 1 to or greater.
  • Examples of such compounds are methoxypolyethylene glycol, ethoxypolyethylene glycol, n-propoxypolyethylene glycol, isopropoxypolyethylene glycol, butoxypolyethylene glycol, phenoxypolyethylene glycol, methoxypolypropylene glycol, methoxypolybutylene glycol, phenoxypolypropylene glycol, phenoxypolybutylene glycol rnethoxypolymethylene glycol, and the like.
  • Suitable polyalkylvinyl ethers having one terminal hydroxyl group are the addition polymers prepared by the homopolymerization of alkylvinyl ethers wherein the alkyl group contains from 1 to 4 carbon atoms.
  • chain-terminating agents examples include hydroxy polymethylvinyl ether, hydroxy polyethylvinyl ether, hydroxy polyprop-ylvinyl ether, hydroxy polybutylvinyl ether, hydroxy polyisobutylvinyl ether, and the like.
  • the chain-terimnating agents or compounds may be employed in the preparation of the modified polyesters, in amounts ranging from 0.05 mole percent to 4.0 mole percent, based on the amount of dicarboxylic acid or dialkyl ester thereof employed in the reaction mixture. It is to be noted that when chain-terminating agents are employed alone, i.e., Without a chain-branching agent, the maximum amount that can be employed in the reaction mixture is 1.0 mole percent.
  • the addition of controlled amounts of chain-branching agents along with the chain-terminating agents allows the introduction of an increased amount of the latter into the polymer chain than is otherwise possible when employing the chain-terminating agents alone.
  • Weight percent of chain-terminating agent which may be employed in this invention will vary with the molecular weight of the agent.
  • the range of average molecular weight of the chain-terminating agents suitable for use in this invention is from 500 to 5000, with those agents having a molecular weight in the range of 1000 to 3500 being preferred.
  • Materials suitable as chain-branching agents or crosslinking agents, which are employed to increase the viscosity or molecular weight of the polyesters, are the polyols which have a functionality greater than two, that is, they contain more than two functional groups, such as hydroxyl.
  • Suitable compounds are pentaerythritol; compounds having the formula wherein R is an alkylene group containing from 3 to 6 carbon atoms and n is an integer from 3 to 6, for example, glycerol, sorbitol hexane triol-l, 2, 6, and the like; compounds having the formula wherein R is an alkyl group containing from 2 to 6 carbon atoms, for example, trimethylol ethane, trimethylol propane, and the like compounds up to trimethylol hexane; and the compounds having the formula F L( 2)u 3 wherein n is an integer from 1 to 6.
  • compounds having the above formula there may be named trimethylol benzene-1,3,5, triethylol benzene-1,3,5, and the like.
  • Aromatic polyfunctional acid esters may also be employed in this invention as chain-branching agents and particularly those having the formula and in which, R, R and R" are alkyl groups containing 1 to 3 carbon atoms and R' is hydrogen or alkyl groups having 1 to 2 carbon atoms.
  • R, R and R" are alkyl groups containing 1 to 3 carbon atoms and R' is hydrogen or alkyl groups having 1 to 2 carbon atoms.
  • compounds having the above formula there may be named trimethyl trimesate, tetramethyl pyromellitate, tetramethyl mellop-honate, trimethyl hemimellitate, trimethyl trimellitate, tetramethyl prehnitate, and the like.
  • mixtures of the above esters which are obtained in practical synthesis.
  • the chain-branching agents or cross-linking agents may be employed in the preparation of the polyesters and copolyesters in amounts ranging from 0.05 mole percent to 2.4 mole percent, based on the amount of dicarboxylic acid or dialkyl ester thereof employed in the reaction mixture.
  • the preferred range of chain-branching agent for use in the present invention is from 0.1 to 1.0 mole percent.
  • the calculated amounts of chain-terminating agent or chain-terminating agent and chain-branching agent or cross-linking agent are charged to the reaction vessel at the beginning of the first stage of the esterification reaction and the reaction proceeds as in any well-known esterification polymerization.
  • the highly polymeric linear condensation polymers selected from the group consisting of polyesters and polyester-amides, which contain in the molecular structure a substantial proportion of recurring groups having the following structural formula CH -CH:
  • substituted cyclohexane ring is selected from the group consisting of the cis and trans isomers thereof may be used in the practice of this invention.
  • These polymeric linear polyesters and polyester-amides may be prepared by a process comprising condensing (1) either of cis or the trans isomer or a mixture of these isomers of l,4-cyclohexanedimethanol alone or mixed with another bifunctional reactant with (2) a bifunctional carboxy compound.
  • the bifunctional reactants which can be employed contain no other reactive substituents which would interfere with the formation of a highly polymeric linear polymer when condensed with 1,4-cyclohexanedimethanol or a mixture thereof with such bifunctional reactants.
  • These 'bifunctional reactants adapted for the preparation of linear condensation polymers are quite well known and have been discussed earlier.
  • the 1,4-cyclohexanedimethanol employed in any of the processes for making condensation polymers can be used in combination with an additional bifunctional coreactant such as when employing a mixture of glycols (it is advantageous to use amounts of the 1,4-cyclohexanedimethanol equal to at least 50 mole percent of the total of such coreactants employed although smaller proportions can also be used).
  • the various bifunctional core actants which can be employed in admixture with 1,4- cyclohexanedimethanol include other glycols and compounds which do not necessarily react with a glycol e.g. an aminoalcohol. Such coreactants also include diamines, or aminocarboxy compounds.
  • the bifunctional reactants containing functional groups which can be condensed with 1,4-cyclohexanedimethanol or mixtures thereof are bifunctional compounds capable of condensation so as to form highly polymeric linear condensation polymers
  • Such bifunctional compounds can be solely inter-reactive with a glycol, e.g. a dicanboxylic acid or they can 'be both (a) coreactive in the sense they can be used in lieu of or as a partial replacement of the glycol in a polyester, and (b) inter-reactive in the sense that they condense with a glycol or a bifunctional compound which can be employed in lieu of a glycol.
  • 6-amino-caproic acid is both coreactive in that the amino group is of the type which can be used in lieu of a hydroxy radical of a glycol and also inter-reactive in the sense that the carboxylic group will react with the hydroxy of a glycol or the amine of a bifunctional compound which can be used in lieu of a glycol.
  • the bifunctional compounds which are solely inter-reactive with a glycol include dicarbox'ylic acids, carbonates, and the like.
  • the other bifunctional inter-reactive compounds include aminocarboxy compounds, or hydroxy carboxy compounds.
  • modified linear condensation polyesters used in accordance with the present invention, have specific viscosities in the range of about 0.1 to about 1.0, which repre- )7 sent fiber-and-filament-forming polymers.
  • Specific viscosity as employed herein, is represented by the formula where sD Rel.
  • N Time of flow of the polymer solution in seconds
  • Time of fiow of the solvent in seconds Viscosity determination on the polymer solutions and solvent are made by allowing said solutions and solvent to flow by gravity at 25 C. through a capillary tube.
  • a polymer solution containing 0.5 percent by weight of the polymer dissolved in a solvent mixture containing two parts by weight of phenol and one part by weight, of 2,4,6-trichlorophenol, and 0.5 per-cent by weight of Water based on the total weight of the mixture was employed.
  • aqueous emulsions which are used in the practice of this invention may contain up to 20 percent solids by weight without exceeding the viscosity limits normally used for conditioning agents used in yarn production, with from about 2 to about 15 percent solids being generally preferred.
  • solids as used herein, there is meant the totality of ingredients exclusive of the aqueous vehicle without regard to physical state.
  • the above-described treating agent is applied to the filaments or fiber immediately during or after spinning and prior to drawing.
  • a conventional and convenient technique of application is to contact the fiber while moving or advancing in the course of production with a roll which is made to rotate so that its lower portion dips into a pan containing the treating composition.
  • the treating agent is pumped from a reservoir to the pan or other container and a constant level is maintained by an overflow pipe or similar device.
  • Other suitable methods and devices may be employed such as the use of a wick or split roll or the fiber may be passed through a bath containing a treating agent.
  • the fibers herein described may be modified by incorporation therein of various modifying agents.
  • suitable modifying agents that may be incorporated into the fibers are pigments, plasticizers, resins, diluents, water repellents, waxes, luster modifying agents, flame repellents, antistatic agents, softeners, and the like.
  • Example 1 Filaments were formed by the melt extrusion of a polyethylene terephthalate polymer modified with approximately 6 percent, based on the weight of the polyethylene terephthalate, of methoxy polyethylene glycol having a molecular weight of about 2,000, and approximately 0.125
  • N-o finish was applied to these filaments.
  • the filaments were than lagged or held for 17 hours at room temperature, about 23 C., after which time they could not be uniformly cold or hot drawn. Additional filaments were lagged 8 days at room temperature at which time they could not be cold drawn, and when hot drawn they were so brittle at a draw ratio of 5.2 that a continuous drawing line could not be maintained over a short time period of 5 minutes.
  • Example 2 Filaments were formed by the melt extrusion of polyethylene terephthalate modified with approximately 6 percent, based on the weight of the polyethylene terephthalate, of methoxy polyethylene glycol having a molecular weight of about 2,000, and approximately 0.125 percent, based on the weight of polyethylene terephthalate, of pentaerythritol. These filaments were then treated with an aqueous emulsion containing 10 percent solids, the solids content of which comprised soya dimethyl ethyl ammonium ethosulfate. The treating agent was applied by means of a rotating roll in an amount such that 0.69 percent solids were deposited on the filaments, based on the weight of the filaments.
  • the filament yarns were then divided into three parts.
  • the first part was immediatelyhot drawn on a conventional draw-twist machine at a draw ratio of 4.41X with excellent results.
  • the second part was lagged for 7 days after which it was hot drawn on a conventional draw-twist machine at a draw ratio of 4.41X with excellent results.
  • the third part was lagged for 31 days after which it was hot drawn on a conventional draw-twist machine at a draw ratio of 4.41X with excellent results.
  • a method of treating polyester filaments which consists essentially of treating said filaments immediately following the extrusion of said filaments with an aqueous consisting essentially of from about 2 to 15 percent by weight of solids, said solids consisting essentially of a cationic surface active quaternary ammonium compound hav ing the formula wherein R represents an alkyl radical having more than 10 carbon atoms and R represents an alkyl radical having less than 5 carbon atoms, lagging said treated filaments for periods of from about 17 hours to about 31 days and thereafter uniformly drawing said treated filaments.
  • polyester is polyethylene terephthalate modified with about 6 percent, based on the weight of the polyethylene tere hthalate, of methoxy polyethylene glycol having a molecular weight of about 2000 and about 0.125 percent, based on the weight of the polyethylene terephthalate, of pentaerythritol.
  • a method of treating polyester filaments which consists essentially of treating said filaments immediately following the extrusion of said filaments with an aqueous emulsion, said solids content of which consists essentially wherein R represents an alkyl radical having more than 10 carbon atoms and R represents an alkyl radical having less than 5 carbon atoms, said solids being deposited on said filaments in an amount of from about 0.1 to 1.5 percent by Weight, based on the weight of said filaments, lagging said treated filaments for periods of from about 17 hours to about 31 days and thereafter uniformly drawing said treated filaments.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Treatment Of Fibers During Manufacturing Processes (AREA)
  • Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
US288522A 1963-06-17 1963-06-17 Treating polyester filament with a surface active compound to permit lagging before drawing Expired - Lifetime US3329758A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
NL133640D NL133640C (en)) 1963-06-17
US288522A US3329758A (en) 1963-06-17 1963-06-17 Treating polyester filament with a surface active compound to permit lagging before drawing
GB24165/64A GB1022035A (en) 1963-06-17 1964-06-10 Improvement in polyester fiber manufacture and products obtained thereby
CH778464A CH440538A (fr) 1963-06-17 1964-06-15 Procédé pour conférer une orientation moléculaire à des filaments de polyesters
LU46326D LU46326A1 (en)) 1963-06-17 1964-06-15
SE7343/64A SE304349B (en)) 1963-06-17 1964-06-16
DE19641494670 DE1494670B2 (de) 1963-06-17 1964-06-16 Verfahren zum verbessern der verstreckbarkeit und der eigenschaften von polyesterfaeden
DK302964AA DK113309B (da) 1963-06-17 1964-06-16 Fremgangsmåde til molekylær orientering af polyesterfilamenter.
FR978502A FR1398690A (fr) 1963-06-17 1964-06-16 Perfectionnements à la production d'articles en polyesters, notamment de fibres en téréphtalate de polyéthylène
NL6406827A NL6406827A (en)) 1963-06-17 1964-06-16
BE649400A BE649400A (en)) 1963-06-17 1964-06-17

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US288522A US3329758A (en) 1963-06-17 1963-06-17 Treating polyester filament with a surface active compound to permit lagging before drawing

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US3329758A true US3329758A (en) 1967-07-04

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US (1) US3329758A (en))
BE (1) BE649400A (en))
CH (1) CH440538A (en))
DE (1) DE1494670B2 (en))
DK (1) DK113309B (en))
FR (1) FR1398690A (en))
GB (1) GB1022035A (en))
LU (1) LU46326A1 (en))
NL (2) NL6406827A (en))
SE (1) SE304349B (en))

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3485913A (en) * 1965-10-20 1969-12-23 Toho Beslon Co New method of manufacturing acrylic fibers and the related products
DE2118316A1 (de) * 1970-04-15 1971-11-04 Societe ue la Viscose Suisse, Emmenbrücke (Schweiz) Verfahren zum Herstellen von PoIyäthylenterephthalat-Fäden
US3669933A (en) * 1970-04-28 1972-06-13 Monsanto Co Thermally stable dyeable polyester fibers having inherent oil stain release properties
US3677687A (en) * 1970-03-23 1972-07-18 Ransdell H Murphy Apparatus for ram forming monolithic plastic articles
US3960686A (en) * 1974-01-04 1976-06-01 Chemische Werke Huls Aktiengesellschaft Method for preparing low pilling effect polyester fiber products
US4052501A (en) * 1972-08-16 1977-10-04 American Cyanamid Company Treatment of polyester filaments with aromatic isocyanate mixture
US4328108A (en) * 1979-09-20 1982-05-04 The Goodyear Tire & Rubber Company Composition for the elimination of circumferential stress cracks in spun polyesters
US4375444A (en) * 1979-09-20 1983-03-01 The Goodyear Tire & Rubber Company Method for the elimination of circumferential stress cracks in spun polyesters
US4975233A (en) * 1988-12-09 1990-12-04 Hoechst Celanese Corporation Method of producing an enhanced polyester copolymer fiber

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Publication number Priority date Publication date Assignee Title
SE392299B (sv) * 1971-08-24 1977-03-21 Du Pont Forfarande och medel for framstellning av garn med dragen och snodd textur
AU6198373A (en) * 1972-11-27 1975-05-01 M & T Chemicals Inc Improving fibre properties

Citations (4)

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Publication number Priority date Publication date Assignee Title
US2668795A (en) * 1951-07-28 1954-02-09 Du Pont White brass plating
US3113956A (en) * 1960-03-07 1963-12-10 Robinette Res Lab Inc Low viscosity quaternary ammonium ethosulfate compositions and methods
US3113369A (en) * 1960-05-02 1963-12-10 Monsanto Chemicals Yarn manufacture and products obtained thereby
US3167531A (en) * 1962-01-24 1965-01-26 Monsanto Co Continuous process for the manufacture of bis(2-hydroxyethyl) terephthalate and low molecular weight polymers thereof

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Publication number Priority date Publication date Assignee Title
US2668795A (en) * 1951-07-28 1954-02-09 Du Pont White brass plating
US3113956A (en) * 1960-03-07 1963-12-10 Robinette Res Lab Inc Low viscosity quaternary ammonium ethosulfate compositions and methods
US3113369A (en) * 1960-05-02 1963-12-10 Monsanto Chemicals Yarn manufacture and products obtained thereby
US3167531A (en) * 1962-01-24 1965-01-26 Monsanto Co Continuous process for the manufacture of bis(2-hydroxyethyl) terephthalate and low molecular weight polymers thereof

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3485913A (en) * 1965-10-20 1969-12-23 Toho Beslon Co New method of manufacturing acrylic fibers and the related products
US3677687A (en) * 1970-03-23 1972-07-18 Ransdell H Murphy Apparatus for ram forming monolithic plastic articles
DE2118316A1 (de) * 1970-04-15 1971-11-04 Societe ue la Viscose Suisse, Emmenbrücke (Schweiz) Verfahren zum Herstellen von PoIyäthylenterephthalat-Fäden
US3715421A (en) * 1970-04-15 1973-02-06 Viscose Suisse Soc D Process for the preparation of polyethylene terephthalate filaments
US3669933A (en) * 1970-04-28 1972-06-13 Monsanto Co Thermally stable dyeable polyester fibers having inherent oil stain release properties
US4052501A (en) * 1972-08-16 1977-10-04 American Cyanamid Company Treatment of polyester filaments with aromatic isocyanate mixture
US4052500A (en) * 1972-08-16 1977-10-04 American Cyanamid Company Drawing isocyanate-treated polyester filaments
US3960686A (en) * 1974-01-04 1976-06-01 Chemische Werke Huls Aktiengesellschaft Method for preparing low pilling effect polyester fiber products
US4328108A (en) * 1979-09-20 1982-05-04 The Goodyear Tire & Rubber Company Composition for the elimination of circumferential stress cracks in spun polyesters
US4375444A (en) * 1979-09-20 1983-03-01 The Goodyear Tire & Rubber Company Method for the elimination of circumferential stress cracks in spun polyesters
US4975233A (en) * 1988-12-09 1990-12-04 Hoechst Celanese Corporation Method of producing an enhanced polyester copolymer fiber

Also Published As

Publication number Publication date
SE304349B (en)) 1968-09-23
NL133640C (en))
GB1022035A (en) 1966-03-09
BE649400A (en)) 1964-12-17
CH440538A (fr) 1967-07-31
DK113309B (da) 1969-03-10
DE1494670B2 (de) 1973-07-12
FR1398690A (fr) 1965-05-07
DE1494670A1 (de) 1970-12-03
LU46326A1 (en)) 1964-12-15
NL6406827A (en)) 1964-12-18

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