US20120152423A1 - Tire having rubber component containing short fiber reinforcement with compatablizer - Google Patents

Tire having rubber component containing short fiber reinforcement with compatablizer Download PDF

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Publication number
US20120152423A1
US20120152423A1 US12/971,326 US97132610A US2012152423A1 US 20120152423 A1 US20120152423 A1 US 20120152423A1 US 97132610 A US97132610 A US 97132610A US 2012152423 A1 US2012152423 A1 US 2012152423A1
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Prior art keywords
rubber
comprised
phr
short
functionalized
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US12/971,326
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English (en)
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Junling Zhao
Martin Paul Cohen
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Individual
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Priority to US12/971,326 priority Critical patent/US20120152423A1/en
Priority to EP11192047.6A priority patent/EP2465898B1/de
Publication of US20120152423A1 publication Critical patent/US20120152423A1/en
Priority to US13/668,403 priority patent/US8501837B2/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • C08L9/06—Copolymers with styrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L15/00—Compositions of rubber derivatives
    • 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
    • Y10T152/00—Resilient tires and wheels
    • Y10T152/10—Tires, resilient
    • Y10T152/10495—Pneumatic tire or inner tube
    • Y10T152/10513—Tire reinforcement material characterized by short length fibers or the like

Definitions

  • the invention relates to a tire having a rubber component which contains short fiber reinforcement with a compatabilizer for the fiber reinforcement.
  • short fibers may be, for example, aramid fiber particularly aramid fiber pulp, nylon fiber, polyester fiber and/or rayon fiber.
  • said short fiber reinforcement is an aramid pulp.
  • compatabilizer is a functionalized sulfur curable elastomer such as, for example, epoxidized natural rubber.
  • Pneumatic rubber tires have various rubber components for which sometimes enhanced stiffness of the rubber composition is a desirable feature.
  • Enhanced stiffness of the rubber composition might be accomplished, for example, by an inclusion of a dispersion of a small content, or amount, of short fiber reinforcement.
  • aramid short fibers in a form of a pulp are used to promote an increase of stiffness for a rubber composition, a practice which is well known by those having skill in such art.
  • the short fiber is a short aramid fiber pulp
  • natural cis 1,4-polyisoprene rubber is used to aid in dispersing the aramid short fiber pulp in a rubber composition.
  • a challenge is therefore presented for enhancing short fiber reinforcement, particularly aramid short fiber pulp reinforcement of rubber compositions.
  • rubber and “elastomer” where used, are used interchangeably, unless otherwise prescribed.
  • rubber composition “compounded rubber” and “rubber compound”, where used, are used interchangeably to refer to “rubber which has been blended or mixed with various ingredients” and the term “compound” relates to a “rubber composition” unless otherwise indicated. Such terms are well known to those having skill in the rubber mixing and rubber compounding art.
  • the term “phr” refers to parts of a respective material per 100 parts by weight of rubber, or elastomer.
  • cure and “vulcanize” are used interchangeably unless otherwise indicated.
  • a tire having a component of a rubber composition containing a dispersion therein of short organic fibers comprised of, based on parts by weight per 100 parts by weight rubber (phr):
  • said short organic fibers are comprised of at least one of aramid fiber (e.g. short aramid fiber pulp), polyester fiber nylon fiber and rayon fiber, preferably said aramid fiber pulp.
  • aramid fiber e.g. short aramid fiber pulp
  • polyester fiber nylon fiber e.g. polyester fiber nylon fiber
  • rayon fiber preferably said aramid fiber pulp.
  • said rubber composition may also contain up to about 50 phr of at least one of clay and calcium carbonate, alternately up to about 10 phr of clay and up to about 50 phr of calcium carbonate.
  • a purpose of the compatabilizer elastomer is to compatabilize said organic short fiber, particularly said short aramid fiber pulp, with said rubber composition.
  • said short organic fiber may be, for example, short aramid fiber pulp.
  • Said compatabilizer elastomer may be, for example, expoxidized cis 1,4-polyisoprene rubber.
  • a method of preparing a rubber composition is comprised of:
  • a tire having a tread comprised of the rubber composition prepared by said method.
  • said method further comprises preparing a tire with a tread comprised of the rubber composition prepared by said method.
  • a significant aspect of this invention is promoting an improved bonding strength between the short fiber and sulfur cured rubber matrix through the inclusion of the functionalized elastomer in the rubber composition, particularly, for example, by use of an epoxidized natural rubber as a compatabilizer for aramid short fiber pulp.
  • the rubber composition may be prepared, for example, in at least one preparatory (non-productive) mixing step in an internal rubber mixer, often a sequential series of at least one, usually two, separate and individual preparatory internal rubber mixing steps, or stages, in which the diene-based elastomer is first mixed with the prescribed silica (if used) and carbon black, aramid short fibers, and compatabilizer elastomer, or aramid short fiber masterbatch with said compatabilizer elastomer, followed by a final mixing step (productive mixing step) in an internal rubber mixer, or optionally on an open mill mixer, where curatives (sulfur and sulfur vulcanization accelerators) are blended at a lower temperature and for a substantially shorter period of time.
  • curatives sulfur and sulfur vulcanization accelerators
  • the rubber mixture (rubber composition) is actually removed from the rubber mixer and cooled to a temperature below 40° C., perhaps to a temperature in a range of about 20° C. to about 40° C. and then added back to an internal rubber mixer for the next sequential mixing step, or stage.
  • a tire component is contemplated to be by conventional means such as, for example, by extrusion, or by calendering, of rubber composition to provide a shaped, unvulcanized rubber component such as a tire tread layer.
  • a tire tread layers
  • Such forming of a tire tread (layers) is well known to those having skill in such art.
  • a tire as a manufactured article, is prepared by shaping and curing the assembly of its components at an elevated temperature (e.g. 140° C. to 170° C.) and elevated pressure in a suitable mold.
  • elevated temperature e.g. 140° C. to 170° C.
  • elevated pressure e.g. 170° C.
  • the rubber composition would be compounded by methods generally known in the rubber compounding art, such as mixing the various sulfur-vulcanizable constituent rubbers with various commonly used additive materials, as herein before discussed, such as, for example, curing aids such as sulfur, activators, retarders and accelerators, processing additives, such as rubber processing oils, resins including tackifying resins, silicas, and plasticizers, fillers, pigments, fatty acid, zinc oxide, waxes, antioxidants and antiozonants, peptizing agents and reinforcing materials such as, for example, carbon black.
  • curing aids such as sulfur, activators, retarders and accelerators
  • processing additives such as rubber processing oils, resins including tackifying resins, silicas, and plasticizers
  • fillers pigments, fatty acid, zinc oxide, waxes, antioxidants and antiozonants
  • peptizing agents and reinforcing materials such as, for example, carbon black.
  • the additives mentioned above are selected and commonly used in conventional amounts.
  • Typical amounts of fatty acids, if used, which can include stearic acid, comprise about 0.5 to about 3 phr.
  • Typical amounts of zinc oxide comprise about 1 to about 5 phr.
  • Typical amounts of waxes comprise about 1 to about 5 phr. Often microcrystalline waxes are used.
  • Typical amounts of peptizers comprise about 0.1 to about 1 phr. Typical peptizers may be, for example, pentachlorothiophenol and dibenzamidodiphenyl disulfide.
  • the vulcanization is conducted in the presence of a sulfur vulcanizing agent.
  • suitable sulfur vulcanizing agents include elemental sulfur (free sulfur) or sulfur donating vulcanizing agents, for example, an amine disulfide, polymeric polysulfide or sulfur olefin adducts.
  • the sulfur vulcanizing agent is elemental sulfur.
  • sulfur vulcanizing agents are used in an amount ranging from about 0.5 to about 4 phr, or even, in some circumstances, up to about 8 phr, with a range of from about 1.5 to about 2.5, sometimes from about 2 to about 2.5, being preferred.
  • Accelerators are used to control the time and/or temperature required for vulcanization and to improve the properties of the vulcanizate.
  • a single accelerator system may be used, i.e., primary accelerator.
  • a primary accelerator(s) is used in total amounts ranging from about 0.5 to about 4, preferably about 0.8 to about 2.5, phr.
  • combinations of a primary and a secondary accelerator might be used with the secondary accelerator being used in smaller amounts (of about 0.05 to about 3 phr) in order to activate and to improve the properties of the vulcanizate.
  • Combinations of these accelerators might be expected to produce a synergistic effect on the final properties and are somewhat better than those produced by use of either accelerator alone.
  • delayed action accelerators may be used which are not affected by normal processing temperatures but produce a satisfactory cure at ordinary vulcanization temperatures.
  • Vulcanization retarders might also be used.
  • Suitable types of accelerators that may be used in the present invention are amines, disulfides, guanidines, thioureas, thiazoles, thiurams, sulfenamides, dithiocarbamates and xanthates.
  • the primary accelerator is a sulfenamide.
  • the secondary accelerator is preferably a guanidine, dithiocarbamate or thiuram compound.
  • the mixing of the rubber composition can preferably be accomplished by the aforesaid sequential mixing process.
  • the ingredients may be mixed in at least two stages, namely, at least one non-productive (preparatory) stage followed by a productive (final) mix stage.
  • the final curatives are typically mixed in the final stage which is conventionally called the “productive” or “final” mix stage in which the mixing typically occurs at a temperature, or ultimate temperature, lower than the mix temperature(s) of the preceding non-productive mix stage(s).
  • the terms “non-productive” and “productive” mix stages are well known to those having skill in the rubber mixing art.
  • FIG. 1 and FIG. 2 graphically present Stress (MPa) versus dynamic Strain (%) at 23° C. for FIG. 1 and at 150° C. for FIG. 2 for curves A, B, C, D, E and F for the Samples in Table 2 of Example I.
  • FIG. 3 graphically presents hysteresis in term of a hysteresis loop test at a constant maximum stress of 5 MPa for curves A, B, C, D, E and F for the Samples in Table 2 of Example I.
  • FIG. 4 and FIG. 5 are graphical presentations of Stress (MPa) versus dynamic Strain (%) at test temperature of 23° C. for FIG. 4 and 150° C. for FIG. 5 for rubber Samples G, H and I in Table 2 of Example I.
  • FIG. 6 and FIG. 7 are graphical presentations of Stress (MPa) versus dynamic Strain (%) for rubber Sample J (Control) and K (Experimental) at 23° C. and 150° C., respectively, of Table 7 in Example II.
  • Rubber compositions were prepared for evaluating an effect of providing short fiber aramid pulp reinforcement in a rubber composition together with an epoxy functionalized natural rubber as a compatibilzer for the short aramid fiber pulp reinforcement.
  • Control rubber Samples A and B are rubber compositions which contain natural cis 1,4-polyisoprene rubber (NR) and epoxidized natural rubber (ENR), respectively, without aramid fiber pulp reinforcement.
  • NR natural cis 1,4-polyisoprene rubber
  • EMR epoxidized natural rubber
  • Comparative rubber Sample C contained cis 1,4-polyisoprene natural rubber with an inclusion of 3 phr of a dispersion of short aramid fiber pulp reinforcement.
  • Experimental rubber Samples D, E and F contained epoxidized natural rubber with an inclusion of 3 phr, 6 phr and 12 phr, respectively, of short aramid fiber pulp reinforcement.
  • the rubber compositions were prepared by mixing the ingredients in sequential non-productive (NP) and productive (PR) mixing steps in one or more internal rubber mixers.
  • Non-Productive Mixing Step (mixed to 160° C.) Natural cis 1,4-polyisoprene rubber 1 100 and 0 Epoxidized natural rubber 2 0 and 100 Antioxidant 3 2 Carbon black (N330) 4 50 Processing oil 5 5 Fatty acid 6 3 Zinc oxide 5 Aramid pulp, short fiber 7 0 and variable Productive Mixing Step (PR), (mixed to 110° C.) Sulfur and sulfur cure accelerators 8 4 1 Natural cis 1,4-polyisoprene rubber 2 Expoxidized cis 1,4-polyisoprene rubber as ENR50 TM, a 50 percent expoxidized natural rubber from Malaysia company 3 Antoxidant of the diamine type 4 Rubber reinforcing carbon black as N330, an ASTM designation 5 Rubber processing oil, primarily aromatic rubber processing oil 6 Fatty acid comprised primarily of stearic acid and a minor amount of other fatty acids comprised primarily of palmitic and oleic acids. 7 Aramid short
  • the rubber Samples were prepared to evaluate the inclusion of short aramid fiber pulp with the expoxidized natural rubber compatabilizer, as illustrated in the following Table 2 with the rubber and aramid fiber pulp reported in terms of parts per 100 parts by weight of rubber (phr) for the rubber Samples A through F.
  • Table 2 also reports a summary of various physical properties.
  • FIGS. 1 and 2 ( FIG. 1 and FIG. 2 ) graphically present Stress (MPa) versus dynamic Strain (%) at 23° C. for FIG. 1 and at 150° C. for FIG. 2 .
  • FIG. 3 ( FIG. 3 ) graphically presents hysteresis in terms of a hysteresis loop test at a constant maximum stress of 5 MPa.
  • FIG. 1 Stress versus Strain at 23° C. using an InstronTM analytical instrument, ASTM D412
  • ASTM D412 Stress versus Strain at 23° C. using an InstronTM analytical instrument, ASTM D412
  • FIG. 1 demonstrates that the interaction of the short aramid fibers had a significantly greater interaction effect for the ENR than for the natural rubber composition.
  • the reduction in hysteresis is considered to be a particularly beneficial effect for the short aramid fiber loaded ENR rubber in a sense that, as the hysteresis effect is reduced, significantly beneficially less internal heat build up in the ENR based rubber composition is expected.
  • Additional rubber compositions were prepared for evaluating an effect of providing epoxidized natural rubber as a compatabilizer for short fiber aramid pulp reinforcement in a rubber composition comprised of cis 1,4-polybutadiene rubber, natural cis 1,4-polybutadiene rubber and isoprene/butadiene rubber (IBR) containing 1.6 phr of the aramid short fiber pulp.
  • a rubber composition comprised of cis 1,4-polybutadiene rubber, natural cis 1,4-polybutadiene rubber and isoprene/butadiene rubber (IBR) containing 1.6 phr of the aramid short fiber pulp.
  • IBR isoprene/butadiene rubber
  • Control rubber Sample G contains elastomers composed of cis 1,4-polybutadiene rubber, natural cis 1,4-polyisoprene rubber and IBR together with reinforcing filler as rubber reinforcing carbon black without the ENR compatabilizer.
  • the rubber compositions were prepared by mixing the ingredients in sequential non-productive (NP) and productive (PR) mixing steps in one or more internal rubber mixers.
  • Non-Productive Mixing Step (mixed to 160° C.) Isoprene/butadiene (IBR) rubber 9 36.75 Cis 1,4-polybutadiene rubber 10 36.75 Natural cis 1,4-polyisoprene rubber 26.5, 20.5, 14.5 Epoxidized natural rubber (ENR50) 0, 6, 12 Antioxidant 3 Carbon black (N550) 51 Resin 11 1.2 Fatty acid 0.5 Zinc oxide 5 Aramid pulp 1.6 Productive Mixing Step (PR), (mixed to 110° C.) Sulfur and sulfur cure accelerators 9.5 9 Tin coupled IBR rubber as a 30/70 isoprene/butadiene rubber from The Goodyear Tire and Rubber Company 10 Cis 1,4-polybutadiene rubber as BUD1208 TM from The Goodyear Tire and Rubber Company 11 non staining, unreactive 100 percent phenol formaldehyde resin
  • the rubber Samples were prepared to evaluate the inclusion of short aramid fiber pulp with the expoxidized natural rubber compatiblizer, as illustrated in the following Table 4 with the rubber and aramid fiber pulp reported in terms of parts per 100 parts by weight of rubber (phr) for the rubber Samples G, H, and I.
  • FIGS. 4 and 5 are graphical presentations of Stress (MPa) versus dynamic Strain (%) at test temperatures of 23° C. and 150° C., respectively, for the aforesaid rubber Samples G, H and I.
  • a fiber masterbatch was prepared by dry blending aramid fiber pulp and epoxidized natural rubber for use in evaluating an effect of using epoxidized natural rubber to aid in compatabilizing the aramid fiber pulp with the rubber composition and to promote bonding strength to the aramid fibers.
  • the aramid fiber/epoxidized natural rubber masterbatch is shown in the following Dry Fiber Masterbatch Table where the amounts are presented in parts of weight per 100 parts of rubber (phr) unless otherwise indicated.
  • Dry Fiber Masterbatch Ingredients Dry Fiber Masterbatch Epoxidized natural rubber (phr) 100 Rubber reinforcing carbon black (N550) (phr) 60 Aramid short fiber pulp (phr) 26.65
  • Rubber compositions were prepared for evaluation an effect of providing short aramid fibers as a pre-formed masterbatch with epoxidized natural rubber with the epoxidized natural rubber being used as a compatiblizer for the aramid fiber to promote improved bonding strength to the aramid fiber.
  • Control rubber Sample J is prepared without the epoxidized natural rubber and Experimental rubber Sample K is prepared with a combination of epoxidized natural rubber and the Fiber Masterbatch rubber sample.
  • the rubber Samples were prepared by mixing the ingredients in sequential non-productive (NP) and productive (P) mixing steps in internal rubber mixers.
  • Table 7 illustrates a summary of rubber Samples followed by a cure behavior as various physical properties of the Rubber Samples based on the basic formulations presented in preceding Table 6 with the parts and percentages presented in terms of weight unless otherwise indicated.
  • Elongation at break for rubber Sample K increased to a value of at least about 170 percent (185 percent for K@L and 173 percent for K@P), an increase of at least about 66 percent compared to a value of about 104 percent for rubber Sample J which did not contain the ENR or fiber/natural rubber masterbatch.
  • FIGS. 6 and 7 are graphical presentations of Stress (MPa) and Strain (%) for rubber Samples J (Control) and K (Experimental) at 23° C. and 150° C., respectively.
  • the K@L curves in FIGS. 6 and 7 represent Stress versus Strain curve for the Stress measurement for Experimental rubber Sample K taken laterally (about 90 degrees or at a right angle) and the K@P curves for the measurement taken in a parallel direction (about 0 degrees) to its grain.
  • Control rubber Sample J (without both ENR compatiblizer and short fiber reinforcement) broke at a strain (elongation) of about 100 percent at a stress (tensile strength) of about 6 MPa, prior to its intended completion of the tests.
  • Experimental rubber Sample K@P broke at a strain (elongation) of 173 percent and a stress of about 14.7 MPa, an increase in strain (elongation) of at least 70 percent and in ultimate stress, or tensile strength, of over 120 percent, compared to rubber Sample J.
  • Experimental rubber Sample K@L broke at a strain (elongation) of 185 percent and a stress (tensile strength) of about 13.7MPa, an increase in strain (elongation) of about 85 percent and in ultimate stress, or tensile strength, of at least 110 percent, compared to rubber Sample J.
  • Control rubber Sample J (without both ENR compatiblizer and short fiber reinforcement) broke at a strain (ultimate elongation at break) of about 69 percent at a stress (tensile strength) of about 3 MPa, prior to its intended completion of the tests.
  • Experimental rubber Sample K@P broke at a strain (elongation) of about 95 percent and a stress (tensile strength) of about 5.8 MPa, an increase in strain (elongation) of at least 70 percent and in ultimate stress, or tensile strength, of over 90 percent, compared to rubber Sample J.
  • Experimental rubber Sample K@L broke at a strain (ultimate elongation) of about 96 percent and a stress (tensile strength) of about 4.8 MPa, an increase in strain (increase in ultimate elongation at break) of about 39 percent and in ultimate stress, or tensile strength, of about 60 percent, compared to rubber Sample J.

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US12/971,326 2010-12-17 2010-12-17 Tire having rubber component containing short fiber reinforcement with compatablizer Abandoned US20120152423A1 (en)

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US12/971,326 US20120152423A1 (en) 2010-12-17 2010-12-17 Tire having rubber component containing short fiber reinforcement with compatablizer
EP11192047.6A EP2465898B1 (de) 2010-12-17 2011-12-06 Reifen mit einer Kautschukzusammensetzung und Kautschukzusammensetzung mit Kurzfaserverstärkung mit einem Kompatibilisierungsmittel
US13/668,403 US8501837B2 (en) 2010-12-17 2012-11-05 Tire having rubber component containing short fiber reinforcement with compatablizer

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITVR20120245A1 (it) * 2012-12-19 2014-06-20 Tumedei S P A Composition for a disc-type flexible coupling and coupling including such composition. - composizione per un giunto flessibile del tipo a disco e giunto includente tale composizione.
CN109517228A (zh) * 2018-11-22 2019-03-26 山东玲珑轮胎股份有限公司 一种含纳米粘土/天然橡胶复合物的新型胎面胶料

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KR101572106B1 (ko) * 2013-08-20 2015-11-26 한국타이어 주식회사 타이어 트레드용 고무 조성물 및 이를 이용하여 제조한 타이어
CN104419199A (zh) * 2013-08-22 2015-03-18 黑龙江鑫达企业集团有限公司 一种芳纶浆粕增强pa66复合材料及其制备方法
WO2017031308A1 (en) 2015-08-18 2017-02-23 University Of Massachusetts Amherst Methods for modification of aramid fibers
CN107286400A (zh) * 2017-08-07 2017-10-24 四川远星橡胶有限责任公司 橡胶履带式接地胶配方及其制备方法
CN108727817A (zh) * 2018-05-21 2018-11-02 北京化工大学常州先进材料研究院 一种聚酰亚胺短切纤维增强母粒及其制备方法
US20230173847A1 (en) * 2021-12-06 2023-06-08 The Goodyear Tire & Rubber Company Pneumatic tire having a fiber-reinforced rubber layer and preparation thereof

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US6598645B1 (en) * 2000-09-27 2003-07-29 The Goodyear Tire & Rubber Company Tire with at least one of rubber/cord laminate, sidewall insert and apex of a rubber composition which contains oriented intercalated and/or exfoliated clay reinforcement
US20060151084A1 (en) * 2001-03-30 2006-07-13 Antonio Serra Tyre for vehicle wheels with a reinforced bead

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WO2008004676A1 (fr) * 2006-07-06 2008-01-10 Bridgestone Corporation Composition de caoutchouc et bandage pneumatique fabriqué à partir de celle-ci
JP4581116B2 (ja) * 2007-09-10 2010-11-17 住友ゴム工業株式会社 加硫ゴム組成物、空気入りタイヤおよびこれらの製造方法

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
US6598645B1 (en) * 2000-09-27 2003-07-29 The Goodyear Tire & Rubber Company Tire with at least one of rubber/cord laminate, sidewall insert and apex of a rubber composition which contains oriented intercalated and/or exfoliated clay reinforcement
US20060151084A1 (en) * 2001-03-30 2006-07-13 Antonio Serra Tyre for vehicle wheels with a reinforced bead

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITVR20120245A1 (it) * 2012-12-19 2014-06-20 Tumedei S P A Composition for a disc-type flexible coupling and coupling including such composition. - composizione per un giunto flessibile del tipo a disco e giunto includente tale composizione.
WO2014097136A1 (en) * 2012-12-19 2014-06-26 Tumedei Spa Composition for a disc-type flexible coupling and coupling including such composition
US9587082B2 (en) 2012-12-19 2017-03-07 Tumedei Spa Composition for a disc-type flexible coupling and coupling including such composition
CN109517228A (zh) * 2018-11-22 2019-03-26 山东玲珑轮胎股份有限公司 一种含纳米粘土/天然橡胶复合物的新型胎面胶料

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EP2465898A1 (de) 2012-06-20
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US8501837B2 (en) 2013-08-06

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