WO2001027196A1 - Composition de caoutchouc, matiere composite et procede de fabrication de ladite matiere composite - Google Patents

Composition de caoutchouc, matiere composite et procede de fabrication de ladite matiere composite Download PDF

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Publication number
WO2001027196A1
WO2001027196A1 PCT/JP2000/007042 JP0007042W WO0127196A1 WO 2001027196 A1 WO2001027196 A1 WO 2001027196A1 JP 0007042 W JP0007042 W JP 0007042W WO 0127196 A1 WO0127196 A1 WO 0127196A1
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WIPO (PCT)
Prior art keywords
rubber
metal
rubber composition
formula
equation
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Ceased
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PCT/JP2000/007042
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English (en)
Japanese (ja)
Inventor
Kunio Mori
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Zeon Corp
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Zeon Corp
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    • 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
    • C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
    • 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

Definitions

  • the present invention relates to a rubber composition having excellent adhesion to a metal material, a composite material of rubber and a metal material (adhesive body of rubber and a metal material), and a method for producing the composite neo.
  • the composite material of the present invention can be applied to a wide range of fields as, for example, seismic isolation rubber, vibration damping rubber, packing, diaphragm, rubber roll, belt, and automobile tire. Background art
  • the bonding technology between rubber and metal materials for example, the surface of metal materials such as ebony method, cyclized rubber method, phenolic resin method, halogenated rubber method, brass plating method, and electroless plating method Processing methods are known. However, none of these surface treatment methods was fully satisfactory.
  • the ebonite method is a method in which a rubber material is coated on a surface of a metal material, and a rubber compound is put on the sheet and heat-pressed.
  • the cyclized rubber method is a method in which a cyclized rubber solution is applied to the surface of a metal material, the solvent is dried, and then the rubber compound is pressed and vulcanized and bonded.
  • the phenol resin method is a method in which a resol-type phenol resin solution is applied to the surface of a metal material, the solvent is dried, and a rubber compound is pressed and bonded by vulcanization.
  • the halogenated rubber method is a method of applying a chlorinated rubber solution or a mixed solution of chlorinated rubber and isocyanate to the surface of a metal material, drying the solvent, and pressing and bonding the rubber compound by vulcanization.
  • the brass plating method is a method in which a brass plating treatment is performed on the surface of a metal material, and an unvulcanized rubber compound containing an organic acid cobalt or sulfur is vulcanized and bonded. This brass plating method is applied to the bonding between steel cord and rubber in a steel radial tire, but there is a problem in the hot water resistance of the obtained composite material.
  • the electroless plating method is a method in which an electroless palladium-phosphorus alloy plating or an electroless nickel-copper-phosphorus alloy plating is applied to the surface of a metal material, and a rubber compound is pressed and vulcanized to the plating-treated surface.
  • a method is known in which a zinc plating treatment is performed on the surface of a metal material, and a rubber compound containing cobalt naphthenate as an adhesion promoter is vulcanized and bonded.
  • this method has a problem in that thermal decomposition of rubber is promoted by cobalt.
  • the nickel plating method has excellent heat resistance and water resistance, has little rubber deterioration, and can be effectively vulcanized and bonded when combined with a rubber vulcanization method using triazine thiols.
  • these various plating methods have a problem that the plating process must be performed on the surface of the metal material, which is troublesome. Moreover, the plating process is mainly applied to metal materials made of iron, copper, brass, etc. There was a problem of being squeezed. For example, according to the nickel plating method, a composite material having excellent adhesiveness and physical properties can be obtained, but it is difficult to perform nickel plating on a metal material made of aluminum magnesium. Therefore, it is difficult to apply it. Disclosure of the invention
  • An object of the present invention is to provide a composite material having excellent adhesiveness at an interface with a metal material by a direct cross-linking (vulcanization) bonding method without applying a surface treatment such as an adhesive application and a plating process to the metal material. It is to provide a rubber composition which can be used.
  • Another object of the present invention is to provide an excellent adhesive property at the interface between rubber and a metal material by a direct cross-linking (vulcanization) bonding method without subjecting the metal material to surface treatment such as application of an adhesive and plating.
  • An object of the present invention is to provide a composite material and a method for producing the same.
  • the present inventor has made intensive studies to overcome the problems of the prior art, and as a result, came to a rubber composition in which a crosslinking agent and a specific organic nickel salt are mixed with rubber.
  • a rubber composition in which a crosslinking agent and a specific organic nickel salt are mixed with rubber.
  • peel strength bonding strength
  • Wood can be given.
  • the present inventor has presumed that when the rubber composition and the metal material are heated under contact, nickel plating due to the organic nickel salt is generated at the interface, whereby strong adhesiveness can be obtained. I have.
  • the present invention is not limited by the bonding mechanism or the bonding theory of the characteristics.
  • the rubber composition of the present invention can be used for aluminum or nickel which is difficult to nickel-plate. It can be directly cross-linked and adhered to a metal material composed of magnesium or an alloy containing these. The rubber composition of the present invention can directly cross-link and adhere to a metal having a greater ionization tendency than nickel or a metal material comprising an alloy containing the metal. The present invention has been completed based on these findings.
  • a rubber According to the present invention, a rubber, a crosslinking agent, and
  • R 2 are each independently a hydrogen atom, a saturated or unsaturated aliphatic hydrocarbon group having 1 to 24 carbon atoms, an aromatic hydrocarbon group, An alkyl-substituted aromatic hydrocarbon group or an alicyclic hydrocarbon group.
  • the present invention provides a rubber composition containing at least one organic nickel salt selected from the group consisting of compounds represented by the following formula:
  • a composite material obtained by directly cross-linking and bonding a rubber composition containing the organic nickel salt and a metal material having an ionization tendency greater than nickel or an alloy containing the metal.
  • the rubber composition containing the organic nickel salt and a metal material having a higher ionization tendency than nickel or a metal material made of an alloy containing the metal are heated in contact with each other.
  • a method for producing a composite material which is directly crosslinked and adhered is provided.
  • Examples of the rubber used in the present invention include natural rubber (NR), isoprene rubber (IR), butadiene rubber (BR), styrene-butadiene rubber (SBR), chloroprene rubber, acrylonitrile-butadiene rubber (NBR), and styrene.
  • NR natural rubber
  • IR isoprene rubber
  • BR butadiene rubber
  • SBR styrene-butadiene rubber
  • NBR acrylonitrile-butadiene rubber
  • EPR ethylene-propylene rubber
  • EPDM ethylene-propylene-gen rubber
  • acrylic rubber
  • cross-linking agent one suitable for the type of each rubber and the performance of the composite (adhesive) can be used.
  • specific examples of crosslinking agents include sulfur, triazine thiols, resin crosslinking agents, polyol crosslinking agents, peroxides, and combinations (mixtures) of two or more of these.
  • Can be The cross-linking agent content can be appropriately determined according to the type of rubber and the performance of the composite material, but in most cases, 0.1 to 5 parts by weight of rubber, which is generally used, is used in 100 parts by weight of rubber. Preferred results can be obtained within the range.
  • a crosslinking accelerator, a crosslinking aid, and the like can be added as necessary, in addition to the crosslinking agent.
  • sulfenamide-based crosslinking accelerators, thiuram-based crosslinking accelerators, thiazole-based crosslinking accelerators, amine-based crosslinking accelerators, polyfunctional monomers, etc. adjust the rubber crosslinking rate and use metal materials. It is effective in increasing the adhesive strength between and.
  • the content of the crosslinking accelerator and the crosslinking aid can be appropriately determined according to the type of the rubber and the performance of the composite material. In many cases, the content is 0.1 to 10 parts by weight based on 100 parts by weight of the rubber. Good results can be obtained in the range of parts by weight.
  • Metal activators such as Zn ⁇ , MgO, Ca ⁇ , and Ca (OH) 2 are used to adjust the vulcanization rate of rubber, improve the properties of vulcanized rubber, and improve adhesive strength.
  • the metal activators can be used alone or as a mixture of two or more.
  • the content of the metal activator can be appropriately determined according to the type of the rubber and the performance of the composite material. In many cases, the content is preferably in the range of 1 to 20 parts by weight relative to 100 parts by weight of the rubber. The result can be obtained.
  • a rubber is combined with a specific organic nickel salt in order to exhibit adhesiveness to a metal material and obtain a composite material of rubber and metal having good adhesive strength.
  • a nickel-plated metal material and a rubber compound containing triazine thiols by heating a nickel-plated metal material and a rubber compound containing triazine thiols by contact heating, the metal material composed of various metals and various rubbers are vulcanized and bonded without using an adhesive. can do.
  • this nickel plating method needs to apply nickel plating to a metal material, and in addition to a metal material made of aluminum or magnesium, which has a high ionization tendency, in particular. It was difficult to apply them, and it was a problem to be solved.
  • a rubber composition comprising a rubber and a cross-linking agent and an organic nickel salt
  • the rubber composition does not require an adhesive and a plating treatment, and thus can be treated with a rubber.
  • a composite material in which the metal material is firmly bonded can be obtained.
  • the organic nickel salt in the rubber composition and the metal on the surface of the metal material are replaced, nickel plating occurs, and the rubber and the metal material are strongly bonded through the nickel plating. Presumed.
  • the rubber contains at least one organic nickel salt selected from the group consisting of compounds represented by the following formulas (I), (II), (III), (IV) and (V). Let it.
  • R 2 each independently represent a hydrogen atom, a saturated or unsaturated aliphatic hydrocarbon group having 1 to 24 carbon atoms, an aromatic hydrocarbon group, an alkyl group, It is a group-substituted aromatic hydrocarbon group or alicyclic hydrocarbon group.
  • these compounds are organic nickel salts, in formulas (I) to (III), and and R 2 are not both hydrogen atoms.
  • R 1 and R 2 may be linear, but the branched one is more excellent in the expression of adhesive strength.
  • organic nickel salts those represented by the formulas (I) and (II) are particularly preferred.
  • organic nickel salt of the formula (I) include (iso—C 7 H 15 COO) 2 Ni.
  • organic nickel salt of the formula (II) include the following formula (Ila)
  • organic nickel salt of the formula (III) include the following formula (Ilia)
  • organic nickel salt of the formula (IV) include the following formula (IVa)
  • organic nickel salt of the formula (V) include the following formula (Va)
  • an organic nickel salt may be generated in situ, in addition to a method of adding the already synthesized organic nickel salt to the rubber.
  • an organic nickel salt is generated. Therefore, an embodiment in which an inorganic nickel compound or the like and an organic acid are added in combination also falls within the scope of the present invention.
  • the content of the organic nickel salt cannot be unambiguously determined as the nickel content because it is related to the molecular weight and the diffusivity of the molecule, but usually 0.1 to 15 parts by weight with respect to 100 parts by weight of rubber. It is preferably 0.5 to 10 parts by weight, more preferably 1 to 5 parts by weight.
  • Each of the organic nickel salts can be used alone, but if desired, two or more can be used in combination. Use a combination of two or more organic nickel salts. Thus, a more favorable result can be obtained in terms of the balance between the adhesiveness and the crosslinkability.
  • the rubber composition of the present invention includes reinforcing agents, fillers, stabilizers, lubricants, softeners, crosslinking regulators, vulcanization retarders, processing aids, processing oils, and the like, which are generally used in the rubber technical field. Can be contained.
  • the reinforcing agent include various grades of carbon black such as HAF and ISA, and silica.
  • the filler include calcium carbonate, c these various additives and the like talc, are used in amounts required in accordance with the respective purposes.
  • the rubber composition of the present invention can be prepared by melt-kneading a rubber, a crosslinking agent, an organic nickel salt, and if necessary, other additives. To suppress premature cross-linking, it is preferable to melt-knead rubber and a reinforcing agent, and then mix and knead a bridging agent, a cross-linking accelerator, and an organic nickel salt. After kneading, the rubber composition can be shaped into a desired shape.
  • a metal material having a higher ionization tendency than nickel is preferably used.
  • the ionization tendency means the tendency of a metal to become a cation when it comes into contact with a liquid, particularly water, and can be quantitatively evaluated by the standard electrode potential of the metal.
  • the order of metal elements in which the ionization tendency with respect to water is arranged in the order of the size is called the ionization sequence, which is arranged in the order of Mg, Al, Zn, Cr, Fe (II), Ni, and the like.
  • a metal material composed of a metal having a higher ionization tendency than nickel or an alloy containing the metal is used.
  • Preferred materials include, for example, iron, chromium, brass (copper-zinc alloy), zinc, aluminum, aluminum alloy, and magnesium.
  • the metal material can have a desired shape such as a plate shape, a linear shape, a roll shape, and a net shape.
  • the metal material can be subjected to a pretreatment such as degreasing, washing with water, phosphate treatment, monochromic phosphate treatment, and chromate rinse.
  • a pretreatment such as degreasing, washing with water, phosphate treatment, monochromic phosphate treatment, and chromate rinse.
  • plating treatment of a metal material is not required, plating treatment may be performed if desired.
  • the rubber composition and the metal material may be cross-linked by heating under contact.
  • a rubber composition formed into a desired shape such as a sheet and a metal material are brought into contact with each other and heated and pressed, crosslinking and bonding occur simultaneously.
  • the specific method of direct cross-linking can be appropriately selected according to the shape of the metal material, the viscosity of the rubber composition, the type of the intended composite material, and the like.
  • the heating temperature and the heating time can also be appropriately set according to the type of the rubber, the type of the crosslinking agent, and the like.
  • a heating time of about 140 to 200 ° C and a heating time of about 5 to 60 minutes are sufficient.
  • a composite material having a high adhesive strength can be obtained.
  • Composite materials of rubber and metal materials include seismic isolation rubber, vibration damping rubber, vibration isolating rubber, packing, diaphragms, gaskets, large rubber rolls, rubber rolls for copiers, conveyor belts, reinforcing belts, and freeway escalators.
  • Examples include handrails, car tires, metal fiber reinforced hoses, etc., and can be used in many fields such as electrical products, electronic products, computer products, automotive 'bus' trucks and airplane parts.
  • t-butylbenzothiazylsulfenamide (BBS) was added as a vulcanization accelerator in the proportions shown in Table 1 when preparing an adhesive rubber sheet using a small experimental roll. Then, an adhesive rubber sheet was produced in the same manner as in the examples. Next, the aluminum sheet and the rubber sheet were bonded together, put into a mold, and heated and pressed at 160 ° C. for 10 minutes to directly crosslink and bond. Table 1 shows the results.
  • Table 1 shows the dibenzothiazyl disulfide (MBTS) used as a vulcanization accelerator when preparing rubber sheets for bonding using small rolls for experiments.
  • MBTS dibenzothiazyl disulfide
  • Example 2 The same procedure as in Example 2 was carried out except that no nickel salt was added and that the heating and pressing time was changed to 30 minutes when producing the rubber sheet for bonding. Table 1 shows the results.
  • Example 3 The same procedure as in Example 3 was carried out except that no nickel salt was added and that the heating and pressing time was changed to 30 minutes when producing the rubber sheet for bonding. Table 1 shows the results.
  • BVS t-butylbenzothiazylsulfenamide
  • MBTS dibenzothiazyldisulfide
  • An SBRZNR blended rubber masterbatch was prepared in the same manner as in Example 1. Next, using a small experimental roll, 4.0 parts of sulfur and the following nickel salt (Ila)
  • Nickel salt (Ila) is replaced with the following nickel salt (Ilia)
  • Nickel salt (Ila) is replaced with the following nickel salt (IVa)
  • Example 73 The same operation as in Example 4 was performed, except that CH 3 COCH— (CH 3 ) CO—Ni—OC (CH 3 ) —CHCOCH 3 (IVa) was used instead. Table 2 shows the results. [Example 73
  • Nickel salt (Ila) is replaced with the following nickel salt (Va)
  • Example 4 The same operation as in Example 4 was performed except that no nickel salt (Ila) was used. Table 2 shows the results.
  • a commercially available aluminum plate (30 ⁇ 50 ⁇ 1 mm) obtained by cutting a pure aluminum plate was degreased with acetone and then dried.
  • Table 3 shows the results.
  • NBR acrylonitrile butadiene rubber
  • EPDM ethylene-propylene-gen rubber
  • triazine trithiol 1.5 parts of 2 5-dimethyl Chiruji t- to Buchiruperuokishi relaxin 5 parts, and nickel salts [(iso _ C 7 H 15 C_ ⁇ _ ⁇ ) 2 N i] 4 parts EPDM rubber masterbatch
  • To prepare an adhesive rubber sheet (thickness 2.2 mm). Thereafter, a composite material was produced in the same manner as in Example 8. Table 3 shows the results.
  • Example 8 The same procedure as in Example 8 was carried out except that no nickel salt was added when producing the rubber sheet for bonding. Table 3 shows the results.
  • Example 9 The same procedure as in Example 9 was carried out except that no nickel salt was added when producing the rubber sheet for bonding. Table 3 shows the results.
  • each formulation shown in Comparative Examples 5 to 7 in Table 3 is a formulation that adheres to the nickel plating treated surface in the nickel plating method. However, as can be seen in Comparative Examples 5-7, these formulations did not Does not adhere at all. On the other hand, in each of the formulations of Examples 8 to 10, since the nickel salt is contained, it can be seen that the aluminum plate and various rubber sheets can be directly cross-linked and adhered.
  • Example 2 In the same manner as in Example 2, an SBRZNR blended rubber master batch and an adhesive rubber sheet were prepared.
  • a soft iron plate (30 ⁇ 50 ⁇ I mm) obtained by degreasing with acetone and then drying was used.
  • Table 4 shows the results.
  • Example 11 was repeated except that the soft iron plate was replaced by a brass plate (30 X 5 O X l mm) which was degreased with acetone and dried. Table 4 shows the results.
  • Example 11 was repeated except that the soft iron plate was replaced with a magnesium plate (30 X 5 O X l mm) which was degreased with acetone and dried. Table 4 shows the results.
  • the vulcanizing agent and (iso _ C 7 H 15 COO ) 2 N if i and was used Gomushi one you want to coexist (Example 1 1-1 3), iron, brass plate, and good in magnetic Shiumu plate It shows excellent adhesiveness. On the other hand, when a rubber sheet containing no nickel salt is used (Comparative Examples 8 to 10), no adhesion is made to these metal plates.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Laminated Bodies (AREA)

Abstract

Composition de caoutchouc qui comporte un caoutchouc, un agent de réticulation et un sel organonickel spécifique, matière composite obtenue par liaison directe de la composition de caoutchouc sur une matière métallique constituée soit d'un métal ayant une tendance à l'ionisation plus forte que celle du nickel, soit d'un alliage dudit métal, pendant la réticulation de la composition, et procédé de production d'une matière composite qui consiste à chauffer la composition de caoutchouc maintenue en contact avec la matière métallique constituée soit d'un métal ayant une tendance à l'ionisation plus forte que celle du nickel, soit d'un alliage dudit métal, pour lier directement la composition à la matière métallique et réticuler ladite composition. Ledit procédé permet d'obtenir une matière composite présentant une excellente adhésion interfaciale à la matière métallique par une technique de liaison/réticulation directe, sans qu'il soit nécessaire de soumettre la matière métallique à un traitement de surface tel que l'application d'un revêtement sous forme d'adhésif ou de placage.
PCT/JP2000/007042 1999-10-14 2000-10-11 Composition de caoutchouc, matiere composite et procede de fabrication de ladite matiere composite Ceased WO2001027196A1 (fr)

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Application Number Priority Date Filing Date Title
JP29259999A JP2001114942A (ja) 1999-10-14 1999-10-14 ゴム組成物、複合材及び複合材の製造方法
JP11/292599 1999-10-14

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102153793A (zh) * 2011-04-18 2011-08-17 青岛茂林橡胶制品有限公司 一种橡胶减震缓冲胶塞及其制备方法
WO2024021647A1 (fr) * 2022-07-23 2024-02-01 浙江天铁实业股份有限公司 Plaque résonante de ballast, procédé de fabrication associé et utilisation associée

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4617579B2 (ja) * 2001-02-08 2011-01-26 横浜ゴム株式会社 タイヤ用ゴム組成物
JP2007098896A (ja) * 2005-10-07 2007-04-19 Daiso Co Ltd 半導電性ゴムローラー用積層体
JP2007186644A (ja) * 2006-01-16 2007-07-26 Yokohama Rubber Co Ltd:The タイヤトレッド用ゴム組成物
JP4767239B2 (ja) * 2007-10-25 2011-09-07 ゲイツ・ユニッタ・アジア株式会社 ベルトおよびベルト材料

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JPS63139970A (ja) * 1986-12-03 1988-06-11 Bridgestone Corp スチ−ル用接着剤ゴム組成物
JPS63289042A (ja) * 1987-05-22 1988-11-25 Sankyo Kasei Kk ジエン系ゴム組成物
JPH02132133A (ja) * 1989-05-26 1990-05-21 Oouchi Shinko Kagaku Kogyo Kk 高分子着色成形材用の耐光安定化剤
JPH1160820A (ja) * 1997-08-12 1999-03-05 Japan Energy Corp 金属とゴムとの接着促進剤

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FR2501700B1 (fr) * 1981-03-16 1985-08-09 Michelin & Cie Compositions a base de caoutchoucs vulcanisables au soufre

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JPS63139970A (ja) * 1986-12-03 1988-06-11 Bridgestone Corp スチ−ル用接着剤ゴム組成物
JPS63289042A (ja) * 1987-05-22 1988-11-25 Sankyo Kasei Kk ジエン系ゴム組成物
JPH02132133A (ja) * 1989-05-26 1990-05-21 Oouchi Shinko Kagaku Kogyo Kk 高分子着色成形材用の耐光安定化剤
JPH1160820A (ja) * 1997-08-12 1999-03-05 Japan Energy Corp 金属とゴムとの接着促進剤

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102153793A (zh) * 2011-04-18 2011-08-17 青岛茂林橡胶制品有限公司 一种橡胶减震缓冲胶塞及其制备方法
CN102153793B (zh) * 2011-04-18 2013-03-20 青岛茂林橡胶制品有限公司 一种橡胶减震缓冲胶塞及其制备方法
WO2024021647A1 (fr) * 2022-07-23 2024-02-01 浙江天铁实业股份有限公司 Plaque résonante de ballast, procédé de fabrication associé et utilisation associée

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