US3687721A - Polyester multifilament yarns - Google Patents

Polyester multifilament yarns Download PDF

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Publication number
US3687721A
US3687721A US825987A US3687721DA US3687721A US 3687721 A US3687721 A US 3687721A US 825987 A US825987 A US 825987A US 3687721D A US3687721D A US 3687721DA US 3687721 A US3687721 A US 3687721A
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United States
Prior art keywords
yarn
composition
weight percent
hlb
finish
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US825987A
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English (en)
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Kimon C Dardoufas
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Allied Corp
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Allied Chemical Corp
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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 oxygen
    • D06M13/224Esters of carboxylic acids; Esters of carbonic acid
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01DMECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D5/00Formation of filaments, threads, or the like
    • D01D5/08Melt spinning methods
    • D01D5/096Humidity control, or oiling, of filaments, threads or the like, leaving the spinnerettes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/62Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40Reduced friction resistance, lubricant properties; Sizing compositions
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50Manufacturing or production processes characterised by the final manufactured product
    • Y02P70/62Manufacturing or production processes characterised by the final manufactured product related technologies for production or treatment of textile or flexible materials or products thereof, including footwear
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber
    • Y10T428/2933Coated or with bond, impregnation or core
    • Y10T428/2964Artificial fiber or filament
    • Y10T428/2967Synthetic resin or polymer

Definitions

  • thermoplastic filaments, fibers, yarns and threads some type of fluid treatment is usually required to maximize inter-filament cohesion during processing to accentuate operability during routine processing in manufacturing the yarn as well as for necessary subsequent operations.
  • Various well known additives are also often added during the manufacture of the yarn in an effort to give better operability during the manufacture of the yarn as well as to give greater resistivity of the yarn to the deteriorating effects of heat and age.
  • the multifilament yarns applicable for use in the present invention are prepared from polyamides and polyesters or from copolymers or coblends thereof.
  • the multifilament yarns particularly applicable for use in the present invention are prepared from polyester and polyamide.
  • the former can be utilized in the present invention whether prepared either by the well known ester interchange reaction between dimethyl terephthalate and an alkylene glycol or the more recently improvised direct esterification process wherein terephthalic acid and an alkylene glycol under certain conditions can directly yield the synthetic linear polyesters from which the polyester yarns are prepared.
  • a relatively heavy coating of fluid must necessarily be "Ice applied to the yarn in order to give proper lubricity allowing greater molecular orientation during subsequent processing with consequent greater strength.
  • a method and composition to allow proper wettability and lubricity is therefore necessary for the preparation of improved industrial yarns.
  • a textile treating fluid usually comprises lubricants, emulsifiers and antistats or wetting agents plus other ingredients necessary to assist in obtaining the desired textile material. Any one ingredient must of necessity interrelate in such a way with all the other ingredients so the overall treating fluid is compatible to the extent of having sufficient wetting ability and therefore give suflicient lubricity to the yarn.
  • the emulsifiers must have a proper HLB value.
  • the HLB value of an emulsifier is defined as their hydrophilic-lipophilic balance.
  • HLB values of 1 to 10 are strongly attracted to the oil phase to be dispersed and are emulsification agents for oils and fats. Values above 10 are strongly attracted to water and are emulsification agents for the aqueous component. The determination of these and other .values are made in accordance with the method depicted in the Kirk-Othmer Encyclopedia of Chemical Technology, vol. 8, 2nd edition, pages 117- 154, John Wiley & Sons, 1965.
  • the antistat and/or wetting agent must be present in such an amount and be of such a composition as to be compatible with high-speed elongation to yield sufficient low static to avoid lick-back in the high-speed drawing apparatus thus permitting drawing of the yarn to sufficiently high-draw ratio to achieve necessary strength characteristics for first quality industrial yarn while maintaining minimal operation difiiculties, such as, low wraps and breaks per pound.
  • the fluid components when deposited on the yarn, must be capable of resisting heat treatment of temperatures in the range of up to about 250 C. without volatilizing or significantly altering the lubricity, static and stability of the composition.
  • the fluid ingredients, when applied to the yarn also must have low yarn to metal frictional characteristics to avoid abrasion and wearing of the processing equipment.
  • Antioxidants may also be used with said fluid to assist in resisting aging and heat deterioration.
  • Another mode of the present invention is attained by providing for the manufacture of multifilament yarn to which has been applied about 0.4 to about 1.5 weight percent based on the weight of the yarn of a liquid coating composition comprising about 13 to about 25 weight percent of said composition selected from the group consisting of glycerol monoleate and decaglycerol tetraoleate with ethoxylated tall oil fatty acids, about 12 to about 20 weight percent of said composition selected from the group consisting of sulfated glycerol trioleate and ethoxylated alkylamine, about 55 to about 75 weight percent of said composition hexadecyl (isocetyl) stearate, and about 1 to about 3 weight percent of said composition of 4,4'-thiobis-( 6-tert-butyl-m-creso1)
  • the lubricants suitable for use in the present invention are a branched chain alcohol combined with a fatty acid having 14 to 22 carbon atoms in the chain and having the general structural formula
  • n n and n are independent integers and wherein n has a value of 4 to 10, n has a value of 6 to 12 and n has a value of 12 to 22.
  • the values of n n and n are :2, 7:3 and 16-33 respectively.
  • More preferably Formula I is hexadecyl stearate (isocetyl stearate) and still more preferably Formula I consists of about 45 weight percent of the above described stearate radical and about 55 weight percent palmitate radical.
  • the amount of lubricant employed in the present invention may vary considerably but a preferred amount is about 65:20 weight percent of the total solids content of the composition. This component is a liquid at 0 C. and has excellent hydrolytic and oxidative stability.
  • esterified branched chain alcohol as shown in Formula I can be replaced with up to 50 weight percent with a triglyceride estcrified with a fatty acid and then rearranged.
  • triglyceride has the general formula as indicated in Formula II,
  • Formula H HC 00 (Cy Hy wherein y y and y are the number of carbon atoms in the fatty acid chain and are independent variable integers having a numerical value of 11 to 17, and y y and y are the number of hydrogen atoms in the fatty acid chain and are independent variable integers having a numerical value of 23 to 35.
  • the triglyceride of the present invention should not exceed about 34 weight percent of the total solid. This component is a liquid at room temperature.
  • Emulsification agents are a most important constituent of the textile treating fluid composition.
  • Suitable emulsification agents for use in the present invention are polymerized glycerol esterified with an unsaturated fatty acid having 14 to 20 carbon atoms in the chain and having the general formula as indicated in Formula III,
  • Z Z Z and z are independent variable integers having a numerical value of 13 to 19 and wherein Z2, Z Z and Z8 are independent variable integers having a numerical value of 27 to 39, and further wherein at least 2 of the fatty acid chains contain at least 1 but not more than 3 double bonds, and still further wherein x x x x and x are either a fatty acid chain or hydrogen and are independently variable with each other.
  • K has a numerical value of 4 to 10 glyceride units.
  • This emulsifier composition has an HLB value of 6.0:11].
  • the preferred component of the emulsification agent is decaglycerol tetraoleate having an HLB value of 6.0.
  • This component of the emulsification agent is generally used in the amount of about 4 to 15 weight percent of the total solids.
  • a second component of the emulsification agent is a glycerol esterified with an unsaturated fatty acid as indicated in Formula IV,
  • R R and R are selected from the group consisting of long chain fatty acids or hydrogen.
  • this component of the emulsification agent is 80 weight percent mono-oleate and 20 weight percent di-, trior unsubstituted glycerols.
  • This preferred form of the component indicates a strong attraction for the oil phase of the emulsion.
  • the third component of the emulsification agent is an ethoxylated tall oil which contains about 15 ethylene oxide units. This ethoxylated tall oil is subdivided into two major chemical groups. The first group is indicated as Formula A,
  • n is an independent variable integer having a numerical value of to 20 and R represents a long chain fatty aliphatic component acid having 13 to 19 carbon atoms and having 27 to 39 hydrogen atoms.
  • the fatty acid constituents are selected from the group consisting of palmitic, linoleic and oleic acids which are condensed with a polyethylene oxide containing 10 to 20 moles of ethylene oxide.
  • the first group represents about 60 weight percent of this component of the emulsification agent.
  • the second group is indicated as Formula B and represents about 40 weight percent of this component of the emulsification agent,
  • n is an independent variable integer having a numerical value of 10 to 20 and R represents alicyclic resin acids which contain 50 to 60 weight percent of a mixture of abietic acid, dehydro abietic acid, levo pimaric acid, palustric acid, neoabietic acid, pimaric acid, isopimaric acid and other terpene acids in small quantities.
  • the tall oil composition containing abietic acid, dehydro abietic acid, levo pimaric acid and palustric acid is the preferred composition of this group as it yields the higher percentage of solids in the emulsions of the ethoxylated tall oil.
  • the preferred tall oil ethylene oxide composition makes up about 6 to 18 percent of the solids in the total finish composition.
  • a lubricant HLB ratio can be determined by taking a weighted average HLB and multiplying this value times the weight percent of the lubricant of the total solids content and dividing by 100.
  • the lubricant compositions having a lubricant HLB ratio of 46:3 have excellent emulsion stability.
  • antistats and/or wetting agents suitable for use in the present invention are a glycerol condensed with unsaturated fatty acid sulfated to about 8 weight percent S0 as indicated in Formula V,
  • n n n n n and n are independent integers having a numerical value of 5 to 9.
  • n n n n n and n are independent integers having a numerical value of 5 to 9.
  • fully sulfated glycerol trioleate is preferable.
  • This component besides being a good antistat and wetting agent also has emulsification properties and an HLB value of greater than 12.
  • This component of the finish composition makes up about 9 to 13 weight percent of the solids in the total finish composition.
  • antistats and/ or wetting agents suitable for use in the present invention are represented as shown in Formula VI,
  • Formula VI /(C2H4 )xH wherein R is an alkyl chain of a fatty amine having 16 to 18 carbon atoms in the chain, and wherein x and y are independent variable integers having a numerical value of 8 to 12.
  • R is an alkyl chain of a fatty amine having 16 to 18 carbon atoms in the chain, and wherein x and y are independent variable integers having a numerical value of 8 to 12.
  • Other long chain alkyl ethoxylated amines may be used provided they are liquid at room temperature and have antistatic properties. These ethoxylated alkyl amines have an HLB value of about 15.5. Further, they become cationic below 7.0 pH and are non-ionic above a pH of 7.0.
  • the use of a mixture of the materials of Formula V and Formula VI being anionic and cationic respectively, results in synergistic increased antistatic properties. It is not understood at this time how this unusual phenomena works.
  • the antioxidants suitable for use in the present invention are 4,4 thio bis-(6-tert-butyl-m-cresol); 2,2 methylene bis(4- chlorophenol); 2-5, ditertiary butyl hydroquinone; 6 dodecyl, 1,2 dihydro 2,2,4 trimethylquinoline; diphenylamine acetone; p-isopropoxy diphenylamine, thio-bis (disec.-amylphenol); trinonylphenyl phosphite and 9,9 dialkyl dihydroacridine.
  • This component of the finish composition may be employed in an amount of 1 to 5 weight percent, preferably about 2 weight percent of the solids in the finish composition.
  • Example 1 A series of finishes (A) through (I) are made up containing the ingredients as indicated in Table I. The ingredients are mixed together in the weight proportions as shown in Table I to form a concentrate. A small percentage of water is added to the concentrate until a clear solution is attained. Then, the concentrate is added slowly to water with good agitation of the aqueous solution to obtain a 35 weight percent as solids. In approximately /1 hour, excellent emulsion stability is obtained. Each solution is made up to contain 35 percent solids and 65 percent water.
  • the contact angles were measured with a refined version of the contact angle goniometer described in the Journal of Colloid Science 1, 513 (1946) by W. C. Bigelow, D. L. Pickett and W. A. Zisrnan.
  • the viscosity of 100 percent concentrate of the various emulsions Prior to addition of water, the viscosity of 100 percent concentrate of the various emulsions is measured using a I Broolclield viscosimeter Model LVT device. This viscosity is measured in centipoises under standard conditions. An ultralow UL-adapter is employed for the viscosity measurement of emulsions which has its own spindle container and uses a #1 spindle. Since the emulsion and concentrate is Newtonian in character, viscosity can be determined directly at C.
  • Table I shows a series of finishes which are evaluated at a 35% solids concentrate and 65% water concentrate level. On dilution, the emulsion viscosities are also determined under the same conditions as that used in determination of the concentrate as described above. In all cases, the emulsions are 35% solids and 65% water.
  • Table II shows the concentrate and emulsion viscosities in centipoises and wetting abilities in degrees of contact angle as well as the emulsion stability of the emulsions made up and illustrated in Table I. From Table II, it can be observed in general where low concentrate viscosities and low emulsion viscosities are obtained, the emulsion stabilities are excellent. However, where hexadecyl stearate is not included in the composition as illustrated by composition F, the emulsion stability is poor, even though the concentrate viscosity and the emulsion viscosity are low.
  • the wetting ability is measured in degrees of constant angle of a drop of each finish on a polyester film a heated zone and passes through essentially quiescent countercurrent quench zones.
  • the yarn exits from the quench zone and the filaments are guided uniformly over a textile fluid finish treatment roll.
  • the yarn After passing over the finish roll, the yarn passes through a guide to provide uniform spreading on the finish roll, thence to a take-up roll.
  • Table III gives the drawn yarn properties and drawing performance. The same finish compositions as indicated in Tables I and II are applied under identical circumstances. The results are shown in Table 111.
  • the textile fluid finish composition of this invention yields tire cord of superior strength and toughness index and superior final breaking strength.
  • the adhesion and the flexural fatigue tests show yarn containing the finish compositions of this invention to be superior to other finish types and to known commercial yarns.
  • Wheel durability tests show the yarn at least equal to or perhaps slightly superior to commercial polyester yarn and with a commercial finish composition employed as a control.
  • Example 14 Polyester chips of the same quality as employed for Examples 2 through are spun in a continuous operation and are drawn to produce a drawn industrial yarn.
  • the yarn has an ultimate tensile strength of -8.5 gins. per denier and an elongation of 13%.
  • the yarn is drawn.
  • 0.7% finish was applied from a 35% aqueous emulsion using the same textile fluid finish composition as indicated by A-I in Table I.
  • the polyester was drawn.
  • Yarns from finish composition A, B and H gave satisfactory and uniform drawing performance. Yarn with finish composition C and E spun and drew only fair. However, yarns containing finish compositions of D, F, G, and I drew so poorly that they could not be strung up at normal speeds.
  • polycaproamide fibers having a formic acid viscosity of 60 are passed over a draw pin and then over a heater, then over a draw roll, then over a winder. The yarn is then drawn.
  • Polycaproamide yarns coated with finish compositions A, B, C and H gave excellent performance. Yarns containing finish compositions C and E gave respectively fair and good performance, whereas yarns D, F, G, and I gave poor performance in the same general pattern as that obtained for the polyesters illustrated in Examples 2 through 10.
  • Example 16 textile fluid finish compositions A-I of Example 1, the weight percent of water was replaced with a low viscosity fluid, tetraethylene glycol di(2- methyl hexoate).
  • the industrial yarn is spin-drawn as in Example 14 with again improved performance for A, B, E and H and somewhat inferior drawing performance and strength properties in C, D, F, G, and I.
  • Other additives suitable for use in the present invention in lieu of the aqueous make-up are kerosene, triethylene glycol dipelargonate, neopentylglycol dipelargonate, octyl-decyladipate, diisooctyl azelate, diethyl hexyl sebacate.
  • Synthetic polyester filamentary yarn comprised of filaments which are treated with from about 0.4 to about 1.5 weight percent based on the weight of the yarn of a liquid composition consisting essentially of an emulsifying agent comprising about 4.9 to about 5.0 weight percent of said composition of decaglycerol tetraoleate, about 5.9 to about 6.0 weight percent of said composition of glycerol monooleate, and about 7.8 to about 8.0 weight percent of said composition of ethoxylated tall oil fatty acid, an antistat and wetting agent comprising about 11.8 to about 12.0 weight percent of said composition of sulfated glycerol trioleate, and about 3.9 to about 4.0 weight percent of said composition of an ethoxylatcd alkylamine and a lubricant of about 55.0 to about 75.0 weight percent of said composition hexadecyl stearate.
  • an emulsifying agent comprising about 4.9 to about 5.0 weight percent of said composition of decaglycerol
  • the yarn of claim 1 wherein the treating materials have an additional ingredient of about 1.0 to about 5.0 weight percent of said composition of an antioxidant consistin g of 4,4'-thiobis- (6-tert-butyl-m-cresol) 3.
  • the lubricant comprises about 30.0 to about 35.0 weight percent of said composition of hexadecyl stearate and about 30.0 to about 35.0 weight percent of said composition of rearranged triglyceride.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US825987A 1969-05-19 1969-05-19 Polyester multifilament yarns Expired - Lifetime US3687721A (en)

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US82598769A 1969-05-19 1969-05-19

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US (1) US3687721A (de)
BE (1) BE749800A (de)
CH (1) CH505918A (de)
DE (1) DE2021850A1 (de)
FR (1) FR2046557A5 (de)
NL (1) NL7006406A (de)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3850658A (en) * 1973-02-05 1974-11-26 Allied Chem Multifilament polyethylene terephthalate yarn
US3859122A (en) * 1973-02-01 1975-01-07 Du Pont Fish composition for draw-texturing yarn
US3940544A (en) * 1974-06-28 1976-02-24 Allied Chemical Corporation Production of polyester yarn
US4052321A (en) * 1976-03-17 1977-10-04 Dixie Yarns, Inc. Flame-retardant yarn or thread containing brominated ester of oleic or linoleic acid
US4103068A (en) * 1976-01-30 1978-07-25 Allied Chemical Corporation Polyester filamentary yarns
US4105568A (en) * 1976-01-30 1978-08-08 Allied Chemical Corporation Finish for polyester filamentary yarns
US4127490A (en) * 1977-12-05 1978-11-28 Basf Wyandotte Corporation Fiber finish compositions
US4210700A (en) * 1978-09-15 1980-07-01 Allied Chemical Corporation Production of polyester yarn
US4293460A (en) * 1980-05-05 1981-10-06 Allied Chemical Corporation Polyamide yarn spin finish containing a rearranged glyceride and oxidized polyethylene
US4382993A (en) * 1981-06-08 1983-05-10 Stokely-Van Camp, Inc. Tire cord finish, polyester cord produced therewith and tires using the polyester cord
US4617236A (en) * 1985-10-21 1986-10-14 Allied Corporation Additives to polyester tire yarn overfinish to reduce dip penetration
US4959267A (en) * 1988-11-23 1990-09-25 Du Pont Canada Inc. Fiber reinforced rubber products
US20160256556A1 (en) * 2013-10-08 2016-09-08 Taiyo Kagaku Co., Ltd. Oil/fat composition containing polyunsaturated fatty acid
US10562355B2 (en) 2013-04-09 2020-02-18 Cooper Tire & Rubber Company Tire bead

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1179105A (en) * 1981-10-30 1984-12-11 Robert M. Marshall Stabilized finish composition

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3859122A (en) * 1973-02-01 1975-01-07 Du Pont Fish composition for draw-texturing yarn
US3850658A (en) * 1973-02-05 1974-11-26 Allied Chem Multifilament polyethylene terephthalate yarn
US3940544A (en) * 1974-06-28 1976-02-24 Allied Chemical Corporation Production of polyester yarn
US4103068A (en) * 1976-01-30 1978-07-25 Allied Chemical Corporation Polyester filamentary yarns
US4105568A (en) * 1976-01-30 1978-08-08 Allied Chemical Corporation Finish for polyester filamentary yarns
US4052321A (en) * 1976-03-17 1977-10-04 Dixie Yarns, Inc. Flame-retardant yarn or thread containing brominated ester of oleic or linoleic acid
US4127490A (en) * 1977-12-05 1978-11-28 Basf Wyandotte Corporation Fiber finish compositions
US4210700A (en) * 1978-09-15 1980-07-01 Allied Chemical Corporation Production of polyester yarn
US4293460A (en) * 1980-05-05 1981-10-06 Allied Chemical Corporation Polyamide yarn spin finish containing a rearranged glyceride and oxidized polyethylene
US4382993A (en) * 1981-06-08 1983-05-10 Stokely-Van Camp, Inc. Tire cord finish, polyester cord produced therewith and tires using the polyester cord
US4617236A (en) * 1985-10-21 1986-10-14 Allied Corporation Additives to polyester tire yarn overfinish to reduce dip penetration
US4959267A (en) * 1988-11-23 1990-09-25 Du Pont Canada Inc. Fiber reinforced rubber products
US10562355B2 (en) 2013-04-09 2020-02-18 Cooper Tire & Rubber Company Tire bead
US20160256556A1 (en) * 2013-10-08 2016-09-08 Taiyo Kagaku Co., Ltd. Oil/fat composition containing polyunsaturated fatty acid
US11382980B2 (en) * 2013-10-08 2022-07-12 Taiyo Kagaku Co., Ltd. Oil/fat composition containing polyunsaturated fatty acid

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NL7006406A (de) 1970-11-23
FR2046557A5 (de) 1971-03-05
CH505918A (de) 1971-05-28
BE749800A (fr) 1970-10-01
DE2021850A1 (de) 1970-11-26
CH656370A4 (de) 1971-05-28

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