EP1664161A1 - Procede de trempage de fibres synthetiques a deux etapes - Google Patents

Procede de trempage de fibres synthetiques a deux etapes

Info

Publication number
EP1664161A1
EP1664161A1 EP04764828A EP04764828A EP1664161A1 EP 1664161 A1 EP1664161 A1 EP 1664161A1 EP 04764828 A EP04764828 A EP 04764828A EP 04764828 A EP04764828 A EP 04764828A EP 1664161 A1 EP1664161 A1 EP 1664161A1
Authority
EP
European Patent Office
Prior art keywords
fiber
latex
dip
blocked
rubber
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.)
Withdrawn
Application number
EP04764828A
Other languages
German (de)
English (en)
Inventor
Hirosuke Watanabe
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.)
Teijin Aramid BV
Original Assignee
Teijin Twaron BV
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
Application filed by Teijin Twaron BV filed Critical Teijin Twaron BV
Priority to EP04764828A priority Critical patent/EP1664161A1/fr
Publication of EP1664161A1 publication Critical patent/EP1664161A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
    • C08J5/06—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials
    • 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
    • D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
    • 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
    • D06M13/395—Isocyanates
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/41—Phenol-aldehyde or phenol-ketone resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2321/00—Characterised by the use of unspecified rubbers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
    • 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
    • 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
    • Y10T428/2933—Coated or with bond, impregnation or core

Definitions

  • the invention relates to a two-step method for dipping a synthetic fiber wherein the fiber is first dipped with a pre-dip composition followed by a dip with resorcinol-formaldehyde latex (RFL) composition.
  • Fibers such as aramid fibers, that are used to adhere to rubber compounds are commonly subjected to a dipping process for enhancing the bonding of such synthetic fibers to rubber.
  • Such compositions may be used in manufacturing composites, for example tires wherein reinforcement fibers are bond to tire rubber compounds.
  • rubber composites which include fiber reinforcement in the form of fibers, continuous filament yarns, cords, or chopped fibers, it is important to enhance the adhesion performance between the rubber matrix of the composite and the reinforced fiber materials.
  • Aramid fiber for example, is a fiber used for tire reinforcement. Providing adhesion between aramid and rubber is very difficult due to the crystalline surface of the fiber. Hence an active pre-dipping process is necessary in order to get a reasonable adhesion performance between fiber and rubber.
  • the standard method of such pre-dipping process is using an epoxy adhesive pre-dipping followed by a resorcinol formaldehyde latex (RFL) dip, which process provides good adhesion to sulfur-cured rubber for aramid reinforcement.
  • RTL resorcinol formaldehyde latex
  • epoxides and polyethyleneimine have been proposed as adhesion promotors for aramid fibers
  • lyengar proposed a two-step adhesive system for aramid fiber adhesion to rubber.
  • the first step or pre-dipping should consist of epoxy compound.
  • Such pre-dip compositions containing mixtures of polyfunctional isocyanates and diisocyanates have been described in JP 51037174, and containing mixtures of blocked polyisocyanates and clay (such as bentonite) have been disclosed in JP 55062269. None of these compositions, however, were very efficient in adhering rubber and none of these were commercially used.
  • the adhesion technology that has been developed since then is virtually always based on the use of epoxides, which is nowadays undesirable because of the ever tightening health care problems and governmental regulations. According to HSE regulations it is undesirable for human body to be exposed to epoxides.
  • a two-step method for dipping a synthetic fiber wherein the fiber is first dipped with an aqueous pre-dip composition followed by a dip with resorcinol-formaldehyde latex (RFL) composition, characterized in that the pre-dip composition comprises a blocked isocyanate having at least tri-functional isocyanate groups and a latex wherein the ratio by weight of blocked isocyanate and latex is between 9 and 0.7, preferably between 4 and 1.
  • RTL resorcinol-formaldehyde latex
  • the pre-dip composition may comprise blocked at least tri-functional isocyanate compound and a latex, which further comprises water, an emulsifier, and 2-vinyl pyridine copolymer.
  • the latex part of the pre-dip may be the same or different of the latex part of the RFL composition, and is a block copolymers of a conjugated olefinic block and an aromatic block.
  • Such block copolymers are known in the art. It was found that particular good results were obtained when the latex part of the pre-dip and the RFL composition is a vinyl-pyridine block copolymer. Suitable copolymers comprise 2- vinyl pyridine, styrene, and butadiene moieties. Preferably, 10-20% of the units in the copolymer are 2-vinyl pyridine-like structures.
  • the method according to this invention can in principle be applied to any synthetic fiber that is commonly used as reinforcement fiber in rubber compositions for tires, transport transmission belts, and the like. Such fibers preferably contain at least one of aramid, polyester, and polyester terephthalate.
  • Particularly useful fibers within the context of the invention are fibers containing at least aramid, preferably containing PPTA and/or PPODPTA.
  • the method according to the invention is suitable for dipping fibers wherein the fiber is used as spun.
  • the blocked isocyanate has at least tri-functional isocyanate groups. Examples of such isocyanates are 1 ,6-hexamethylene diisocyanate (HDI) trimer, etc.
  • Blocking groups are known in the art and are selected from ketoxime groups such as methyl ethyl ketoxime, pyrazole derivatives such as 3,5-dimethylpyrazole, esters such as malonic acid esters, caprolactam, and alkylated phenol.
  • blocked isocyanate is a blocked HDI-trimer, such as methyl ethyl ketoxime or 3,5-dimethylpyrazole blocked hexamethylene diisocyanate trimer. Most preferred blocking group is 3,5-dimethylpyrazole.
  • the RFL dip may contain an emulsifier. Suitable emulsifiers are selected from emulsifiers comprising rubber latex.
  • a very suitable pre-dip according to the invention is a composition comprising 2.5 to 4 wt.% of water-dispersed 3,5-dimethylpyrazole blocked isocyanate compound (HDI-trimer), 1 to 2.5 wt.% of 2-vinyl pyridine copolymer (latex) and 90 to 96 wt.% of water (wt.% based on solids). It is essential that the ratio by weight of blocked isocyanate and latex is between 9 and 0.7. Compositions containing too much or too little latex do not give adhesive properties that are comparable with those of the conventional epoxy pre- dips.
  • HDI-trimer water-dispersed 3,5-dimethylpyrazole blocked isocyanate compound
  • latex 2-vinyl pyridine copolymer
  • 90 to 96 wt.% of water wt.% based on solids. It is essential that the ratio by weight of blocked isocyanate and latex is between 9 and 0.7. Compositions containing too much or too little latex
  • the invention thus provides a process for adhering aramid fibers to sulfur-vulcanizable rubbers comprising the steps of (1) immersing fibers in an aqueous dispersion which is comprised of (a) 2.5 to 4 wt.% of water-dispersed 3,5-dimethylpyrazole blocked isocyanate compound (HDI-trimer), (b) 1 to 2.5 wt.% of 2-vinyl pyridine copolymer and (c) 90 to 96 wt.% of water to produce coated fibers; (2) drying and curing the coated fibers to produce pre-dipped fibers; (3) subjecting the pre-dipped fibers to a RFL adhesive dip to produce dipped fibers; (4) drying and curing the dipped fibers to produce dipped fibers; (5) placing the cured dipped fibers in contact with a sulfur-vulcanizable rubber; and (6) curing the vulcanizable rubber (wt.% based on solids).
  • an aqueous dispersion which is
  • the invention in another embodiment relates to fibers and cords, wherein the fibers or cords have distributed over at least a surface portion thereof (1) a blocked tri-functional isocyanate, such as water-dispersed 3,5-dimethylpyrazole blocked isocyanate compound (HDI-trimer); (2) a RFL adhesive; and (3) an in situ vulcanized rubber compound.
  • a blocked tri-functional isocyanate such as water-dispersed 3,5-dimethylpyrazole blocked isocyanate compound (HDI-trimer); (2) a RFL adhesive; and (3) an in situ vulcanized rubber compound.
  • Example 1 This example provides testing using aramid test sample to show the effect of using a tri-functional blocked isocyanate with 2-vinyl pyridine copolymer together on aramid fibers.
  • Adhesives Control adhesive for aramid fiber is a double coat of epoxy and RFL. Aramid fiber was dipped with poly-functional epoxy resin pre-dipping and RFL top-coat for comparison.
  • Experimental adhesive (sub-coat) consists of Trixene® Bl 7986 (3,5- dimethylpyrazole blocked HDI trimer; ex Baxenden Chemicals Ltd., UK) at 3.5 wt.% and Pliocord® VP106S (2-vinyl pyridine copolymer latex; ex Goodyear Chemicals Ltd, USA) at 1.5 wt.% (base on solids) as pre-dipped and RFL as top-coat.
  • the aramid cord was prepared with construction of 2 ply yarns. 1680 dtex PPTA yarn (Twaron®, ex Teijin) or 1670 dtex PPODPTA yarn (Technora®, ex Teijin) was twisted as Z direction with 330 tpm. By cabling, two twisted yarns were combined and twisted as S direction with 330 tpm.
  • This greige cord was dipped in pre-dipping adhesive and dried at 150° C for 120 sec and cured at 240° C for 90 sec, dipped in RFL, and cured at 235° C for 90 sec. Compound for testing Dipped aramid cords were tested in the compound for passenger car tire ply rubber. Main component is natural rubber.
  • HDI-trimer/latex dip wt. ratio HDI-trimer/2-vinyl pyridine (Vp) latex
  • Adhesion performance SPAF performance was determined with NR rubber and NR/SBR rubber for epoxide/RFL (prior art) and non-epoxide/RFL (invention) in both two-steps and direct cabling, and were shown to be almost the same under all conditions. All values were within the range between 280 and 320 N/2 cm.
  • Rubber coverage Rubber coverage was determined as follows. After measuring the peeling adhesion, the peeled surface was observed and the ratio of remained rubber was determined. Results are given in Table III.

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne un procédé à deux étapes permettant le trempage d'une fibre synthétique, consistant à tremper d'abord la fibre dans une composition aqueuse de prétrempage, puis à la tremper dans une composition résorcine-formol-latex (RFL). Ce procédé est caractérisé en ce que la composition de prétrempage contient un isocyanate séquencé comprenant au moins trois groupes isocyanate trifonctionnels et un latex, le rapport pondéral entre l'isocyanate séquencé et le latex étant compris entre 0 et 0,7, et préférence entre 4 et 1. L'invention concerne en outre une composition de prétrempage destinée au trempage d'une fibre synthétique, composée d'un composé isocyanate séquencé au moins trifonctionnel et d'un latex, d'eau, d'un émulsifiant, et d'un copolymère 2-vinyle-pyridine, ainsi qu'une fibre ou un cordon, et un article composite de caoutchouc et de fibre ou de cordon, la fibre ou le cordon comprenant (1) un composé isocyanate trifonctionnel séquencé, de préférence un trimère HDI; (2) un adhésif RFL, et (3) un composé de caoutchouc vulcanisé in situ, répartis sur au moins une partie de sa surface.
EP04764828A 2003-09-12 2004-09-04 Procede de trempage de fibres synthetiques a deux etapes Withdrawn EP1664161A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP04764828A EP1664161A1 (fr) 2003-09-12 2004-09-04 Procede de trempage de fibres synthetiques a deux etapes

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP03020731 2003-09-12
PCT/EP2004/009877 WO2005026239A1 (fr) 2003-09-12 2004-09-04 Procede de trempage de fibres synthetiques a deux etapes
EP04764828A EP1664161A1 (fr) 2003-09-12 2004-09-04 Procede de trempage de fibres synthetiques a deux etapes

Publications (1)

Publication Number Publication Date
EP1664161A1 true EP1664161A1 (fr) 2006-06-07

Family

ID=34306758

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04764828A Withdrawn EP1664161A1 (fr) 2003-09-12 2004-09-04 Procede de trempage de fibres synthetiques a deux etapes

Country Status (6)

Country Link
US (1) US20060280942A1 (fr)
EP (1) EP1664161A1 (fr)
JP (1) JP2007505228A (fr)
CN (1) CN100523057C (fr)
RU (1) RU2346015C2 (fr)
WO (1) WO2005026239A1 (fr)

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DE102017212455A1 (de) 2017-07-20 2019-01-24 Continental Reifen Deutschland Gmbh Verfahren zur Herstellung eines Fahrzeugreifens und Fahrzeugreifen hergestellt nach dem Verfahren und Verwendung von behandelten Festigkeitsträgern
DE102017222894A1 (de) 2017-12-15 2019-06-19 Continental Reifen Deutschland Gmbh Verfahren zur Herstellung eines Festigkeitsträgers zur Verstärkung von Gummiprodukten, Festigkeitsträger sowie Verwendung des Festigkeitsträgers
CN108589305A (zh) * 2018-01-08 2018-09-28 江苏太极实业新材料有限公司 一种纤维骨架材料用浸胶液
PL3597686T3 (pl) * 2018-07-19 2021-04-19 Ems-Patent Ag Kompozycja kąpieli zanurzeniowej do obróbki wkładek wzmacniających
EP3670582B1 (fr) * 2018-12-21 2024-03-20 Indorama Ventures Luxembourg Holding S.A. Procédé de fabrication d'un matériau de renfort
EP3702521A1 (fr) 2019-03-01 2020-09-02 Continental Reifen Deutschland GmbH Composition aqueuse de trempage
EP3702522A1 (fr) 2019-03-01 2020-09-02 Continental Reifen Deutschland GmbH Composition aqueuse de trempage
EP3702523A1 (fr) 2019-03-01 2020-09-02 Continental Reifen Deutschland GmbH Composition aqueuse de trempage
EP3702524A1 (fr) 2019-03-01 2020-09-02 Continental Reifen Deutschland GmbH Composition aqueuse de trempage
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Also Published As

Publication number Publication date
US20060280942A1 (en) 2006-12-14
RU2346015C2 (ru) 2009-02-10
JP2007505228A (ja) 2007-03-08
CN100523057C (zh) 2009-08-05
RU2006112004A (ru) 2006-08-27
CN1849362A (zh) 2006-10-18
WO2005026239A1 (fr) 2005-03-24

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