EP0582904A2 - Fil de polyester avec bonne adhésion au caoutchouc constitué de filaments âme-gaine avec deux types differents de polyesters - Google Patents

Fil de polyester avec bonne adhésion au caoutchouc constitué de filaments âme-gaine avec deux types differents de polyesters Download PDF

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Publication number
EP0582904A2
EP0582904A2 EP93112116A EP93112116A EP0582904A2 EP 0582904 A2 EP0582904 A2 EP 0582904A2 EP 93112116 A EP93112116 A EP 93112116A EP 93112116 A EP93112116 A EP 93112116A EP 0582904 A2 EP0582904 A2 EP 0582904A2
Authority
EP
European Patent Office
Prior art keywords
core
sheath
polyester
mol
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP93112116A
Other languages
German (de)
English (en)
Other versions
EP0582904A3 (fr
EP0582904B1 (fr
Inventor
Johannes Anthonij Dr. Juijn
Leonardus Antonius Godfried Busscher
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Akzo Nobel NV
Original Assignee
Akzo NV
Akzo Nobel NV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Application filed by Akzo NV, Akzo Nobel NV filed Critical Akzo NV
Publication of EP0582904A2 publication Critical patent/EP0582904A2/fr
Publication of EP0582904A3 publication Critical patent/EP0582904A3/fr
Application granted granted Critical
Publication of EP0582904B1 publication Critical patent/EP0582904B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • D01F8/00—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof
    • D01F8/04—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers
    • D01F8/14—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers with at least one polyester as constituent
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2929—Bicomponent, conjugate, composite or collateral fibers or filaments [i.e., coextruded sheath-core or side-by-side type]
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2929—Bicomponent, conjugate, composite or collateral fibers or filaments [i.e., coextruded sheath-core or side-by-side type]
    • Y10T428/2931—Fibers or filaments nonconcentric [e.g., side-by-side or eccentric, etc.]
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2967—Synthetic resin or polymer
    • Y10T428/2969—Polyamide, polyimide or polyester

Definitions

  • the present invention relates to a polyester yarn with good rubber adhesion from core-sheath threads with two different types of polyesters and a process for its production.
  • the present invention was based on the object of avoiding the process step of applying the abovementioned adhesion promoters and of providing new polyester yarns with good rubber adhesion from core-sheath threads for which there is also insufficient adhesion between the core and sheath even with very large core / sheath Relationships of the threads is no longer present.
  • the polyester yarns of core-sheath threads according to the invention are initially characterized in that the core of the core-sheath threads consists of a high-melting thread-forming polyester.
  • the core of the core-sheath threads consists of a high-melting thread-forming polyester.
  • all high-melting thread-forming polyesters and copolyesters such as polyethylene glycol terephthalate, poly (ethylene-2,6-naphthalenedicarboxylate), poly (1,4-dimethylenecyclohexane terephthalate) and their mixed polyesters based on high homopolyester fractions, are suitable for this.
  • the core of the core sheath threads consists at least essentially of polyethylene glycol terephthalate.
  • this copolyester can contain the co-components customary in the production of stretched polyester structures, such as, for example, isophthalic acid, p-hydroxybenzoic acid, p, p'-diphenyldicarboxylic acid, all possible naphthalenedicarboxylic acids, hexahydroterephthalic acid, adipic acid, sebacic acid and glycols, such as 1,4-dihydroxymethylcyclohexane , Tetramethylene, hexamethylene and decamethylene glycol, etc.
  • the preferred polyesters and copolyesters for the core of the core-sheath threads should have the highest possible viscosity, i.e. have a relative solution viscosity of at least 1.8, preferably from 1.9 to 2.3, measured at 25 ° C. as a 1% strength by weight solution in the m-cresol, and have a melting point of at least 250 ° C.
  • the desired high viscosity values can be achieved using known methods, e.g. the condensation in the melt, an additional post-condensation in the melt without or with condensation accelerator (s) or the post-condensation in the solid state.
  • the polyester yarns of core-sheath threads according to the invention are further characterized in that the sheath of the core-sheath threads consists of a high-melting unsaturated copolyester which, based on the dicarboxylic acid components, contains one or more unsaturated dicarboxylic acid co-component (s) at least 2 mol% of alkyl maleic acid with an alkyl group of 1 to 18 carbon atoms and / or alkylene succinic acid of 1 to 18 carbon atoms and / or their polyester-forming derivatives has been prepared.
  • s unsaturated dicarboxylic acid co-component
  • all high-melting thread-forming agents are suitable for the said polyester modification with the unsaturated dicarboxylic acid components
  • Polyester and copolyester structures that are used for the core of the core-sheath threads, but especially those that contain at least 90 mol% of ethylene glycol terephthalate units.
  • unsaturated dicarboxylic acid components citraconic acid and itaconic acid and their polyester-forming derivatives are preferred, which are used in amounts of at least 2 mol%, based on the dicarboxylic acid components.
  • the sheath of the core-sheath threads consists of an unsaturated copolyester which contains 95 to 98 mol% of ethylene glycol terephthalate units and 2 to 5 mol%, preferably 3 to 4 mol%, of citraconic acid and / or itaconic acid and / or their polyester-forming derivatives has been produced.
  • Ethylene glycol alone is preferably used as the glycol component of such unsaturated copolyesters.
  • Preferred polyester-forming derivatives of citraconic acid and itaconic acid are, in particular, citraconic anhydride, dimethyl citraconate and dimethyl itaconic acid.
  • antioxidants such as (5-tert-butyl-4-hydroxy-3-methyl-benzyl) -malonic acid di-n-octadecyl ester (Irganox 420), octadecyl-3- (3,5-di - tert-butyl-4-hydroxy-phenyl) propionate (Irganox 1076), 1,1-bis (5-tert-butyl-4-hydroxy-2-methyl-phenyl) butane (Irganox 414), Tetrakis [methylene (3,5-di-tert-butyl-4-hydroxyhydrocinnamate)] - methane (Irganox 1010), N, N'-1,6-hexamethylene-bis-3- (3,5-di-ter
  • the above unsaturated dicarboxylic acid components can also be used in larger amounts, e.g. 8 mol%, are condensed. In general, however, 5 mol% of the unsaturated dicarboxylic acid components, based on the total of all dicarboxylic acid components, are sufficient for copolyesters which contain at least 90 mol% of ethylene glycol terephthalate units. With larger amounts of unsaturated dicarboxylic acids, this type of copolyester would result in a less advantageous melting point drop to less than 245 ° C.
  • Unsaturated copolyesters which contain, for example, 96 mol% of ethylene glycol terephthalate units and 4 mol% of ethylene glycol citraconate or 4 mol% of ethylene glycol itaconate units, have a melting point of 248.9 and 246.8 ° C., respectively, so that the required dipping of cord yarns without any temperature change can be easily carried out at 240 ° C.
  • the important freezing temperatures T g are 79 ° C or 76 ° C in the same order, so they differ only slightly from the freezing temperature of the homopolyester polyethylene glycol terephthalate, which is 80 ° C, which is particularly advantageous for the stretchability of the bicomponent yarns.
  • the appropriate modification amount of alkyl maleic and / or alkylene succinic acids can easily be determined by determining their melting points and freezing temperatures.
  • the copolyesters preferred for the sheath of the core-sheath filaments generally have a relative solution viscosity of at least 1.5, preferably 1.6 to 2.0, measured at 25 ° C. as a 1% strength by weight solution in m-cresol , and a melting point of at least 245 ° C.
  • the yarns according to the invention are preferably produced from core-sheath threads according to the procedure described in EP 0 398 221 A1.
  • the extruded core component is fed via a first spinneret plate to a second spinneret plate in a plurality of individual streams, with each core component individual stream flowing around the extruded jacket component between the first and second spinneret plates, the two components being spun together, stretched and wound up, and the jacket component is exposed to a flow resistance at least around the area of the individual flows of the core component.
  • a wire mesh is particularly suitable as flow resistance.
  • the weight ratio of the different core / shell polymers can be varied within wide limits, the core polymer with the shell polymer is preferably melt spun in a weight ratio of 95: 5 to 80:20.
  • the core-shell-polymer combinations according to the invention can be spun at the same speeds as the core-shell threads intended for tire cords made of polyethylene glycol terephthalate and polyamide 66 from EP 0 398 221 A1, for example at a speed of 500 m / min or 900 m / min.
  • the polyester yarn is then in a first drawing stage to about 1: 3 and in one second drawing stage to a total drawing ratio of about 1: 5, while the total drawing ratio in the case of the first-mentioned spinning speed is about 1: 6.
  • the core-sheath combinations according to the invention can also be rapidly spun with the spinning speeds of 3000-5000 m / min customary in the rapid spinning of polyester monocomponent yarns.
  • the polyester yarns thus obtained are then drawn to about 1: 1.8 to 1: 1.2 in a first drawing stage and to a total drawing ratio of about 1: 2.4 to 1: 1.6 in a second drawing stage.
  • the polyester yarns thus obtained generally have a tensile strength of 600 to 850 mN / tex, an elongation at break of 10 to 14% and a rubber adhesion of 180 to 260 N. / 2 cm on. While maintaining the usual physical data of polyester yarns intended for tire cords, the surprisingly high values for rubber adhesion make it possible to dispense with the previous use of the specific adhesion promoters described above.
  • the polycondensation was terminated when a relative viscosity of about 1.6, measured at 25 ° C. as a 1% strength by weight solution in m-cresol, was ended.
  • the polycondensation time fluctuated between 2 and 3 hours.
  • Irganox 1330 0.5% by weight of Irganox 1330 was added to the reactants at the time of addition of the modifying unsaturated comonomers.
  • the yarns were spun at a core to sheath ratio of 90:10 parts by weight.
  • Its core consisted of a polyethylene glycol terephthalate with a relative viscosity of 2.04, always measured at 25 ° C as a 1% by weight solution in m-cresol.
  • the sheath polymer consisted of the mixed polyesters produced, which are listed in the table and whose relative viscosity was about 1.6.
  • the 5-zone temperatures of the extruder for the polyethylene glycol terephthalate as the core polymer were in the descending direction between 310 ° C ⁇ 297 ° C.
  • a measuring pump ensured a throughput of about 100 g / min when spinning at a spinning speed of 900 m / min.
  • the throughput for the core polymer was about 126 g / min for the spinning speed of 4000 m / min.
  • the 5-zone temperatures of the extruder for the respective mixed polyester as jacket polymer were in the descending direction between 302 ° C ⁇ 281 ° C.
  • a measuring pump ensured a throughput of approximately 11 g / min when spinning at a spinning speed of 900 m / min.
  • the throughput for the sheath polymer was 14 g / min.
  • the core-shell polymers were spun according to the procedure described in EP 0 398 221 A1.
  • a 60 mesh stainless wire mesh was used as flow resistance.
  • the spinneret plate contained 36 nozzles with a diameter of 500 ⁇ m, the temperature of the spin pack was kept at 297 ° C.
  • a heating channel with a length of 40 cm and a wall temperature of 310 ° C was mounted directly under the spinneret plate.
  • the spun bicomponent yarns were consolidated with side air at a temperature of 20 ° C and a speed of 30 cm / min.
  • core-sheath threads were produced from polyethylene glycol terephthalate at a speed of 900 m / min, the core and sheath of which consisted of the same homopolymer with a relative viscosity of 2.04.
  • the yarns to be drawn contained 180 filaments.
  • the first stretching was carried out on heated stretching pins at a temperature of 80 ° C.
  • the draw ratio of the yarns spun at 900 m / min or at 4000 m / min was varied slightly in the order mentioned, from approximately 1: 3 or 1: 1.4, so that the main draw point was on the fifth draw pin.
  • the second drawing was carried out in a steam chamber with a steam temperature of 245 ° C, the residence time of the yarn in the Steam chamber was 3 seconds. In all cases, the total draw ratio of the yarns spun at 900 m / min or at 4000 m / min was 1: 5 and 1: 1.8, respectively.
  • the following table shows the yarn properties.
  • the yarns obtained were then twisted into a 1100 dtex X1Z435X2S435 tire cord.
  • This cord is treated in a known manner with an aqueous dispersion based on resorcinol-formaldehyde precondensate and vinylpyridine-styrene-butadiene latex (RFL), an order of 5% by weight solids content being set on the cord.
  • RRL vinylpyridine-styrene-butadiene latex
  • the dipped cords were vulcanized into a rubber mixture in the form of strips in accordance with ASTM D 4393-85 and the rubber adhesion was measured in N / 2 cm, ie as a release force for the 2 cm wide strips. The results are shown in the table as average values of 6 measurements each.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Multicomponent Fibers (AREA)
  • Artificial Filaments (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP93112116A 1992-08-10 1993-07-29 Fil de polyester avec bonne adhésion au caoutchouc constitué de filaments âme-gaine avec deux types differents de polyesters Expired - Lifetime EP0582904B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4226369 1992-08-10
DE4226369 1992-08-10

Publications (3)

Publication Number Publication Date
EP0582904A2 true EP0582904A2 (fr) 1994-02-16
EP0582904A3 EP0582904A3 (fr) 1994-11-23
EP0582904B1 EP0582904B1 (fr) 1998-04-22

Family

ID=6465198

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93112116A Expired - Lifetime EP0582904B1 (fr) 1992-08-10 1993-07-29 Fil de polyester avec bonne adhésion au caoutchouc constitué de filaments âme-gaine avec deux types differents de polyesters

Country Status (7)

Country Link
US (1) US6242095B1 (fr)
EP (1) EP0582904B1 (fr)
JP (1) JPH06158432A (fr)
BR (1) BR9303327A (fr)
DE (1) DE59308426D1 (fr)
ES (1) ES2116372T3 (fr)
MX (1) MX9304488A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2306384A (en) * 1995-10-26 1997-05-07 Hoechst Celanese Corp Rubber-polyester composites for tyres
GB2306383A (en) * 1995-10-26 1997-05-07 Hoechst Celanese Corp Rubber-polyester composites for tyres

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8764302B2 (en) * 2002-03-26 2014-07-01 Kureha Gosen Co., Ltd Tape-shaped molding and belt for ball chain
DE202011005577U1 (de) † 2011-04-21 2012-07-24 Rehau Ag + Co Schlauch zur Führung von Fluiden
WO2017065303A1 (fr) * 2015-10-14 2017-04-20 株式会社ブリヂストン Fibres pour renforcement de caoutchouc, conjugué caoutchouc-fibres et pneumatique mettant en oeuvre ce conjugué

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1929070A1 (de) * 1968-07-09 1970-01-15 Goodyear Tire & Rubber Copolyesterharze
EP0201114A1 (fr) * 1985-04-04 1986-11-12 Akzo Nobel N.V. Procédé de fabrication de fil industriel de polyester et câblé fabriqué au moyen de ce fil et objets élastomères renforcés avec ce câblé
EP0398221A1 (fr) * 1989-05-16 1990-11-22 Akzo Nobel N.V. Fil de filaments "âme-gaine" et son procédé de fabrication

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1073183A (en) * 1963-02-05 1967-06-21 Ici Ltd Leather-like materials
BE774518A (fr) 1970-11-02 1972-02-14 Snam Progetti Fibres et filaments conjugues de caracteristiques ameliorees etleur procede de fabrication
FR2278348A2 (fr) * 1974-06-28 1976-02-13 Rhone Poulenc Ind Articles chirurgicaux bioresorbables
US4551378A (en) * 1984-07-11 1985-11-05 Minnesota Mining And Manufacturing Company Nonwoven thermal insulating stretch fabric and method for producing same
JPS6269822A (ja) * 1985-09-19 1987-03-31 Chisso Corp 熱接着性複合繊維
JPH01314729A (ja) * 1988-02-04 1989-12-19 Sumitomo Chem Co Ltd 複合繊維およびその不織成形体
US5252397A (en) * 1990-09-28 1993-10-12 Chisso Corporation Modified polyester resin and hot-melt-adhesive conjugate fibers using the same
US5201689A (en) * 1990-11-05 1993-04-13 Akzo N.V. Stiff cord

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1929070A1 (de) * 1968-07-09 1970-01-15 Goodyear Tire & Rubber Copolyesterharze
EP0201114A1 (fr) * 1985-04-04 1986-11-12 Akzo Nobel N.V. Procédé de fabrication de fil industriel de polyester et câblé fabriqué au moyen de ce fil et objets élastomères renforcés avec ce câblé
EP0398221A1 (fr) * 1989-05-16 1990-11-22 Akzo Nobel N.V. Fil de filaments "âme-gaine" et son procédé de fabrication

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2306384A (en) * 1995-10-26 1997-05-07 Hoechst Celanese Corp Rubber-polyester composites for tyres
GB2306383A (en) * 1995-10-26 1997-05-07 Hoechst Celanese Corp Rubber-polyester composites for tyres

Also Published As

Publication number Publication date
ES2116372T3 (es) 1998-07-16
MX9304488A (es) 1994-02-28
JPH06158432A (ja) 1994-06-07
EP0582904A3 (fr) 1994-11-23
DE59308426D1 (de) 1998-05-28
EP0582904B1 (fr) 1998-04-22
BR9303327A (pt) 1994-03-22
US6242095B1 (en) 2001-06-05

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