WO2015005568A1 - 신규 카다놀 기반 유기 가황제, 이의 제조방법 및 이를 이용한 타이어용 고무배합 조성물 - Google Patents

신규 카다놀 기반 유기 가황제, 이의 제조방법 및 이를 이용한 타이어용 고무배합 조성물 Download PDF

Info

Publication number
WO2015005568A1
WO2015005568A1 PCT/KR2014/003236 KR2014003236W WO2015005568A1 WO 2015005568 A1 WO2015005568 A1 WO 2015005568A1 KR 2014003236 W KR2014003236 W KR 2014003236W WO 2015005568 A1 WO2015005568 A1 WO 2015005568A1
Authority
WO
WIPO (PCT)
Prior art keywords
vulcanizing agent
cardanol
integer
based organic
organic vulcanizing
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.)
Ceased
Application number
PCT/KR2014/003236
Other languages
English (en)
French (fr)
Korean (ko)
Inventor
이홍대
김진환
박제환
윤주영
박기운
보티하이
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.)
M&B GREENUS Co Ltd
Original Assignee
M&B GREENUS Co Ltd
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 M&B GREENUS Co Ltd filed Critical M&B GREENUS Co Ltd
Priority to US14/369,799 priority Critical patent/US20160130421A1/en
Priority to CN201480000565.8A priority patent/CN104520369A/zh
Priority to IN5833DEN2014 priority patent/IN2014DN05833A/en
Priority to RU2014143726A priority patent/RU2014143726A/ru
Priority to JP2015526489A priority patent/JP2015527348A/ja
Priority to EP14729571.1A priority patent/EP3020756A4/en
Publication of WO2015005568A1 publication Critical patent/WO2015005568A1/ko
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/375—Thiols containing six-membered aromatic rings
    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B60C1/0016—Compositions of the tread
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/16—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • 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
    • C08K5/13—Phenols; Phenolates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L21/00—Compositions of unspecified rubbers
    • 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

Definitions

  • the present invention relates to a novel cardanol-based organic vulcanizing agent, a method for preparing the same, and a rubber compound composition for a tire using the same, more specifically, excellent rubber processability and rubber compounding property prepared by reacting cardanol and powdered sulfur which are cashew nut extracts. It relates to a cardanol-based organic vulcanizing agent, a manufacturing method thereof and a rubber compound composition for a tire using the same.
  • vulcanizing agents such as sulfur, metal oxides and organic peroxides are applied to unsaturated double bonds in the chain polymer rubber, the rubber molecules become a kind of network-bonded polymer rubber, which becomes an elastomer, which is called vulcanization. Time, pressure, etc. are mentioned.
  • Natural rubber has the advantage that it is not only stretchable but also waterproof, but has the disadvantage of being sticky when heated and easily broken when cold.
  • the solution to this drawback is the vulcanization method, which has been found by Charles Goodyear in 1839 to vulcanize raw rubber to sulfur to increase its elasticity and to solve the problem of stickiness at high temperatures and breakage at low temperatures. Essentially used throughout rubber and synthetic rubber.
  • the vulcanizing agent is appropriately selected and used according to the composition of the polymer, the molecular distribution state, the structure, and the like, and can be generally divided into an organic vulcanizing agent and an inorganic vulcanizing agent.
  • the organic vulcanizing agent is a drug that vulcanizes by releasing the sulfur contained in the structure to bond the polymer chain of the rubber to form a crosslinked shape, and includes an active sulfur releasing organic vulcanizing agent, oximes, dinitroso compounds, synthetic resins and polyamines.
  • Polyfunctional organic vulcanizing agents and peroxide vulcanizing agents are examples of the sulfur contained in the structure to bond the polymer chain of the rubber to form a crosslinked shape.
  • the present invention is prepared by reacting the organic substance and powder sulfur extracted from cashew nut, which is a natural product, has not only physical properties and rubber compounding properties for excellent rubber processing, but also eco-friendly and economical cardanol-based organic vulcanizing agent and It is an object to provide a rubber compound composition for tires using the same.
  • the present invention to solve the above object provides a method for producing a cardanol-based organic vulcanizing agent comprising the step of reacting cashew nut extract and powder sulfur.
  • the cashew nut extract may be cardanol.
  • the manufacturing method may be to react 1 to 10 parts by weight of powdered sulfur to 100 parts by weight of cashew nuts extract.
  • the reaction may be performed at 130 to 200 °C.
  • the manufacturing method may further comprise the step of dissolving the product produced by reacting the cashew nut extract and powdered sulfur in a solvent to purify.
  • the solvent may be one or more selected from the group consisting of ethyl acetate, n-hexane and ether.
  • the solvent may be 150 to 200 parts by weight based on 100 parts by weight of cardanol-based organic vulcanizing agent.
  • the cardanol-based organic vulcanizing agent may be represented by the following formula (1) or formula (2).
  • n is 1 or 2 and integer, R1 is H or methyl, R2 is hydrogen or a hydroxyl group, R3 is a C n 'H 2n' + 1 (n ' it is 2 to Any one of 5), R is H, S n '' H (n '' is an integer of 1 to 5) or Each of the -S groups may be the same or different)
  • n is an integer of 1 or 2
  • R1 is H or methyl
  • R2 is hydrogen or a hydroxy group
  • R is H
  • Each of the -S groups may be the same or different)
  • the cardanol-based organic vulcanizing agent may be represented by the following formula (3), (4) or (5).
  • the present invention provides a cardanol-based organic vulcanizing agent represented by the formula (1) or formula (2), prepared according to the above production method.
  • the present invention also provides a rubber compound composition comprising the cardanol-based organic vulcanizing agent.
  • the composition may include 1 to 2 parts by weight of the cardanol-based organic vulcanizing agent, 50 to 70 parts by weight of silica, and 10 to 30 parts by weight of carbon black based on 100 parts by weight of the raw rubber. have.
  • the composition may be for a tire tread.
  • the expected driving mileage (FPS), tensile strength (T / S, Tensile strength), unvulcanized properties and wet road traction properties are significantly improved compared with conventional vulcanizing agents. And it contributes to improving the actual vehicle wear performance of the tire as a final product using the bar, can be usefully applied to the rubber compound composition for the tire used in the rubber vulcanization process for tire tread.
  • 1 is a result of FT-IR analysis of cardanol-based organic vulcanizing agent and cardanol according to an exemplary embodiment of the present invention.
  • the present invention provides a method for preparing a cardanol-based organic vulcanizing agent comprising reacting cashew nut extract and powdered sulfur.
  • the present invention is a natural organic material containing an alkyl group having at least one, preferably at least two, double bonds in the molecule, replacing synthetic materials such as alkyl phenols, which are the main raw materials of the organic vulcanizing agent, which is an organic material extracted from cashew nuts. Use cardanol.
  • Cashew nut extraction method in the present invention is not particularly limited as long as it is known to those skilled in the art.
  • Cashew nut extract in the present invention may be cardanol (cardanol).
  • Cardanol an extract extracted from cashew nuts, includes an alkyl group having a plurality of intramolecular double bonds. Analysis of cardanol by GC / MS showed that the number of double bonds in the alkyl group differs depending on the raw material producer / manufacturer. For a specific example, the manufacturer analyzed the two different cardanol in detail, and the following is the main component structure of the cardanol analyzed by the GC / MS analyzer. Monoene in the case of one double bond, diene in the case of two, and triene in the case of three.
  • Cardanol in the present invention may be 20 to 70% of the monoene ratio (monoene + diene + triene), preferably 20 to 50%, more preferably 20 to 40%.
  • the wear performance may be degraded.
  • the cardanol may have a diene + triene ratio of (Diene + Triene) of 20 to 70% based on (monoene + diene + triene), preferably 30 to 70%, more preferably 50 To 65%.
  • Cardanol in the present invention is preferably a high diene + triene (Diene + Triene) content in the cardanol.
  • the production method may be to react 10 to 100 parts by weight of powdered sulfur to 100 parts by weight of cashew nuts extract.
  • 20 to 40 parts by weight of powder sulfur may be reacted with 100 parts by weight of cardanol which is a cashew nut extract.
  • the powdered sulfur may be divided into small amounts in the cardanol, which is a cashew nut extract, and may be sequentially added to the powdered sulfur. At this time, it is preferable to add the divided feed rate while watching the degree of heat generation.
  • the reaction may be carried out at 130 to 200 ° C, preferably 130 to 180 ° C, more preferably 150 to 180 ° C. If the reaction temperature is less than 130 °C powder sulfur is not completely melted and the reactivity with the cashew nut extract cardanol is very weak, if the reaction temperature is above 200 °C can be decomposed again to obtain a product of the desired structure.
  • the production method may further include the step of dissolving the product produced by reacting the cashew nut extract and powdered sulfur in a solvent, thereby improving the purity of the vulcanizing agent produced.
  • the solvent used in the present invention is not particularly limited, but the solvent may be at least one selected from the group consisting of ethyl acetate, n-hexane and ether, and preferably ethyl acetate.
  • cardanol which is a cashew nut extract
  • cardanol-based organic vulcanizing agent 10 to 100 parts by weight of powdered sulfur
  • cardanol-based organic vulcanizing agent 10 to 100 parts by weight of powdered sulfur
  • cardanol-based organic vulcanizing agent 10 to 100 parts by weight of powdered sulfur
  • cardanol-based organic vulcanizing agent 150 to 100 parts by weight of cardanol-based organic vulcanizing agent obtained in a crude state.
  • Purified cardanol-based organic vulcanizing agents can be prepared by dissolving and purifying with 200 parts by weight of solvent.
  • 30 to 40 parts by weight of cardanol, 20 to 30 parts by weight of powdered sulfur, and 150 to 200 parts by weight of a cashew nut extract may be applied.
  • the modified organic vulcanizing agent produced by the production method of the present invention may be represented by the following formula (1) or (2).
  • n is 1 or 2 and integer, R1 is H or methyl, R2 is hydrogen or a hydroxyl group, R3 is a C n 'H 2n' + 1 (n ' it is 2 to Any one of 5), R is H, S n '' H (n '' is an integer of 1 to 5) or Each of the -S groups may be the same or different)
  • n is an integer of 1 or 2
  • R1 is H or methyl
  • R2 is hydrogen or a hydroxy group
  • R is H
  • Each of the -S groups may be the same or different)
  • organic vulcanizing agent may be represented by the following Formula 3, Formula 4 or Formula 5.
  • the preparation method according to the present invention can be represented by the following scheme.
  • the novel cardanol-based organic vulcanizing agent prepared according to the production method of the present invention has a high sulfur content, thereby significantly improving the low sulfur content, which has been pointed out as a problem of the organic vulcanizing agent utilizing an existing alkylphenol resin, It is eco-friendly because it is obtained, and it is economical because the low cost of cardanol itself can significantly lower the manufacturing cost.
  • the rubber composition prepared using the same shows that the tensile strength and the unvulcanized property are equal to or higher than those of the conventional organic vulcanizing agent, and the expected running mileage (FPS) of the tire manufactured using the same is very excellent. This can be confirmed in Experimental Example 1 to be described later.
  • the present invention also provides a rubber compound composition comprising the cardanol-based organic vulcanizing agent.
  • the rubber compound composition of the present invention may include 1 to 2 parts by weight of the cardanol-based organic vulcanizing agent, 50 to 70 parts by weight of silica, and 10 to 30 parts by weight of carbon black based on 100 parts by weight of the raw rubber.
  • the raw material rubber is not particularly limited as long as it is a rubber normally used by those skilled in the art.
  • the rubber compound composition of the present invention in addition to the novel cardanol-based organic vulcanizing agent according to the present invention described above, may be a mixture of conventional vulcanizing agents.
  • the rubber compound composition according to the present invention includes a novel cardanol-based organic vulcanizing agent having excellent physical properties, and thus has excellent mileage and wet road surface traction properties, and thus may be particularly useful as a tire tread composition.
  • the product was dissolved in an ethyl acetate solvent to remove the unreacted reactant from the reaction vessel outer wall and the reactant, and the unreacted reactant was removed by filtering.
  • Ethyl acetate and the resulting modified organic vulcanizing agent were separated using an evaporator, and the separated cardanol based novel organic vulcanizing agent was sufficiently dried in an electric oven.
  • the novel cardanol-based organic vulcanizing agent produced exhibited physical properties of 30.1% sulfur, 0.8% volatiles and 0% ash. The degree of reaction was confirmed by FT-IR and NMR analysis for the cardanol and the prepared cardanol-based organic vulcanizing agent.
  • FT-IR analysis results of cardanol and prepared cardanol-based organic vulcanizing agent are shown in FIG. 1
  • NMR analysis results of cardanol are shown in FIG. 2
  • NMR analysis results of the prepared cardanol-based organic vulcanizing agent are shown in FIG. 3. It was.
  • the product was dissolved in an ethyl acetate solvent to remove the unreacted reactant from the reaction vessel outer wall and the reactant, and the unreacted reactant was removed by filtering.
  • Ethyl acetate and the resulting modified organic vulcanizing agent were separated using an evaporator, and the separated cardanol-based organic vulcanizing agent was sufficiently dried in an electric oven.
  • the prepared cardanol-based organic vulcanizing agent showed physical properties of 36.2% sulfur content, 0.9% volatile matter, and 0% ash.
  • vulcanizing agent-1 inorganic sulfur
  • CZ N-cyclohexyl-2-benzothiazol sulfenamide
  • vulcanizing agent-1 refers to inorganic sulfur used for general purposes.
  • Comparative Example 1 As in the composition of Table 2, except that the vulcanizing agent-1 of Comparative Example 1 is partially replaced with the novel cardanol-based organic vulcanizing agent according to Example 1, and the same composition and processing as Comparative Example 1 A rubber compound composition was prepared by the method.
  • Comparative Example 1 As shown in the following Table 2, except that the vulcanizing agent-1 of Comparative Example 1 was partially replaced with a cardanol-based new organic vulcanizing agent according to Example 2, and the same composition and processing as Comparative Example 1 A rubber compound composition was prepared by the method.
  • Examples 3 and 4 of the rubber compound composition containing a novel cardanol-based organic vulcanizing agent according to the present invention can be confirmed that the tensile strength (T / S) is improved compared to Comparative Example 1 , 0 ° C. Tan ⁇ (wet road traction) was also found to be significantly improved than Comparative Example 1. Indices related to 60 ° C Tan ⁇ (rolling resistance) were also significantly improved. In addition, it showed significantly improved physical properties than Comparative Example 2, a commercially available organic vulcanizing agent, in particular, it can be seen that the FPS (predicted mileage) physical properties significantly improved.
  • Examples 3 and 4 which are tires to which the novel cardanol-based organic vulcanizing agent according to the present invention is applied, showed a significantly higher wear performance than Comparative Example 1, and Example 3 was compared with Comparative Example 2 and Similar performance was shown.
  • Example 4 showed significantly better wear performance than Comparative Example 1, Comparative Example 2, and Example 3, it was confirmed that the more excellent the performance of the raw material with a higher diene content in the cardanol.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Heating, Cooling, Or Curing Plastics Or The Like In General (AREA)
  • Moulds For Moulding Plastics Or The Like (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/KR2014/003236 2013-07-12 2014-04-15 신규 카다놀 기반 유기 가황제, 이의 제조방법 및 이를 이용한 타이어용 고무배합 조성물 Ceased WO2015005568A1 (ko)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US14/369,799 US20160130421A1 (en) 2013-07-12 2014-04-15 Novel cardanol-based organic vulcanizing agent, method for preparing the same, and rubber compound composition for tires using the same
CN201480000565.8A CN104520369A (zh) 2013-07-12 2014-04-15 新的基于腰果酚的有机硫化剂、其制备方法及使用其的轮胎用橡胶复合组合物
IN5833DEN2014 IN2014DN05833A (enExample) 2013-07-12 2014-04-15
RU2014143726A RU2014143726A (ru) 2013-07-12 2014-04-15 Новый органический вулканизирующий агент на основе карданола, способ его получения и содержащая его каучуковая композиция для шин
JP2015526489A JP2015527348A (ja) 2013-07-12 2014-04-15 新規のカルダノールベース有機加硫剤、その製造方法及びそれを用いたタイヤ用ゴム配合組成物
EP14729571.1A EP3020756A4 (en) 2013-07-12 2014-04-15 Novel cardanol-based organic vulcanizing agent, production method for same and blended rubber composition for tyres using same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2013-0082035 2013-07-12
KR20130082035 2013-07-12
KR10-2014-0041658 2014-04-08
KR1020140041658A KR101577651B1 (ko) 2013-07-12 2014-04-08 신규 카다놀 기반 유기 가황제, 이의 제조방법 및 이를 이용한 타이어용 고무배합 조성물

Publications (1)

Publication Number Publication Date
WO2015005568A1 true WO2015005568A1 (ko) 2015-01-15

Family

ID=52570707

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2014/003236 Ceased WO2015005568A1 (ko) 2013-07-12 2014-04-15 신규 카다놀 기반 유기 가황제, 이의 제조방법 및 이를 이용한 타이어용 고무배합 조성물

Country Status (9)

Country Link
US (1) US20160130421A1 (enExample)
EP (1) EP3020756A4 (enExample)
JP (1) JP2015527348A (enExample)
KR (2) KR101577651B1 (enExample)
CN (1) CN104520369A (enExample)
IN (1) IN2014DN05833A (enExample)
RU (1) RU2014143726A (enExample)
TW (1) TW201502187A (enExample)
WO (1) WO2015005568A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025202879A1 (en) * 2024-03-29 2025-10-02 Tata Chemicals Limited A cardanol based coupling agent and a process for preparing it

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105733021B (zh) * 2016-03-09 2019-04-02 中胶橡胶资源再生（青岛）有限公司 一种橡胶再生活化剂及其制备方法
CN108607528B (zh) * 2018-05-08 2021-02-05 东北大学 一种硅藻土/硫化聚合物汞离子吸附材料及其制备方法
EP3868737A4 (en) * 2018-10-16 2022-10-05 China Petroleum & Chemical Corporation PHENOLIC DERIVATIVE, METHOD FOR PREPARATION AND USE
CN111057042B (zh) * 2018-10-16 2022-12-13 中国石油化工股份有限公司 一种酚类衍生物及其制备方法、用途
CN111057041B (zh) * 2018-10-16 2022-12-13 中国石油化工股份有限公司 一种硫化酚酯类衍生物及其制备方法、用途
CN113493718B (zh) * 2020-03-18 2023-03-10 中国石油化工股份有限公司 一种船舶用中速筒状活塞式发动机润滑油组合物及其制备方法
CN113430031B (zh) * 2020-03-23 2023-03-10 中国石油化工股份有限公司 一种润滑脂及其制备方法
KR102399217B1 (ko) * 2020-07-13 2022-05-18 금호석유화학 주식회사 기능화 가공조제, 그의 제조방법 및 그를 포함하는 고무 조성물
CN113321855B (zh) * 2021-05-06 2022-05-20 北京化工大学 一种低生热高耐磨白炭黑/橡胶复合材料及其制备方法和应用
KR102584286B1 (ko) * 2021-09-13 2023-10-05 금호석유화학 주식회사 타이어 트레드용 고무 조성물 및 그 제조방법
WO2025202882A1 (en) * 2024-03-29 2025-10-02 Tata Chemicals Limited A novel coupling agent and a process for preparing it
CN119463313B (zh) * 2024-10-12 2025-09-02 山东华盛橡胶有限公司 一种高抗湿滑、低噪音的电动汽车轮胎及其制备方法
CN119775642B (zh) * 2024-12-26 2025-08-08 扬州泽创鞋业有限公司 一种超耐磨防滑橡胶鞋底材料及其制备方法
CN120535836A (zh) * 2025-07-04 2025-08-26 东莞市烨晟塑料有限公司 一种pvc用耐热钙锌稳定剂及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR19990012315A (ko) * 1997-07-29 1999-02-25 홍건희 타이어 트레드용 고무 조성물
KR0179712B1 (ko) * 1995-12-29 1999-05-15 홍건희 타이어 비드 필러용 고무 조성물
KR20030062174A (ko) * 2002-01-16 2003-07-23 엘지전선 주식회사 고내구성 고무조성물
KR20090113037A (ko) * 2008-04-25 2009-10-29 금호타이어 주식회사 타이어 고무조성물

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3175016B2 (ja) 1991-10-08 2001-06-11 横浜ゴム株式会社 高硬度ゴム組成物
US5760114A (en) * 1996-08-26 1998-06-02 The Goodyear Tire & Rubber Company Rubber compound containing aminobenzylamine
DE10004427A1 (de) * 2000-02-02 2001-10-04 Martin Stielau Verfahren zur Herstellung von Polyurethan
US6828383B2 (en) * 2002-12-13 2004-12-07 Occidental Petroleum Phenolic modified resorcinolic resins for rubber compounding
JP5478809B2 (ja) * 2007-03-20 2014-04-23 東洋ゴム工業株式会社 ゴム組成物及び空気入りタイヤ
JP5382495B2 (ja) * 2008-08-29 2014-01-08 住友ゴム工業株式会社 ゴム組成物およびそれを用いた空気入りタイヤ

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR0179712B1 (ko) * 1995-12-29 1999-05-15 홍건희 타이어 비드 필러용 고무 조성물
KR19990012315A (ko) * 1997-07-29 1999-02-25 홍건희 타이어 트레드용 고무 조성물
KR20030062174A (ko) * 2002-01-16 2003-07-23 엘지전선 주식회사 고내구성 고무조성물
KR20090113037A (ko) * 2008-04-25 2009-10-29 금호타이어 주식회사 타이어 고무조성물

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025202879A1 (en) * 2024-03-29 2025-10-02 Tata Chemicals Limited A cardanol based coupling agent and a process for preparing it

Also Published As

Publication number Publication date
KR101577651B1 (ko) 2015-12-17
US20160130421A1 (en) 2016-05-12
CN104520369A (zh) 2015-04-15
IN2014DN05833A (enExample) 2015-05-15
KR20150007930A (ko) 2015-01-21
EP3020756A1 (en) 2016-05-18
KR20150143398A (ko) 2015-12-23
JP2015527348A (ja) 2015-09-17
TW201502187A (zh) 2015-01-16
RU2014143726A (ru) 2016-08-10
EP3020756A4 (en) 2017-04-12

Similar Documents

Publication Publication Date Title
WO2015005568A1 (ko) 신규 카다놀 기반 유기 가황제, 이의 제조방법 및 이를 이용한 타이어용 고무배합 조성물
CN101228223B (zh) 用于轮胎的包含有机硅偶合剂和无机填料遮盖剂的橡胶组合物
JP5450093B2 (ja) シリル化コアポリスルフィドを含有するタイヤ組成物および部品
US7119147B2 (en) Rubber composition
EP1672017B1 (de) Kautschukmischungen
US11124632B2 (en) Rubber composition for tires, and pneumatic tires
DE50001624D1 (de) Kautschukmischung
CZ295645B6 (cs) Polyorganosiloxany s funkční sírou
CZ222497A3 (cs) Směsi organosilanpolysulfanů a způsob výroby kaučukových směsí obsahujících tyto směsi
EP2612882B1 (de) Kautschukmischungen
KR101240602B1 (ko) 유기 실리카 함유 마스터 배치 탄성체 및 그 제조방법
BR102020004308A2 (pt) Borracha reforçada contendo óleo de triglicerídeo sililado
WO2017074050A1 (ko) 카본블랙의 표면 개질 방법
EP0969033A2 (de) Neue oligomere Organosiliciumverbindungen, deren Verwendung in Kautschukmischungen und zur Herstellung von Formkörpern
KR102696145B1 (ko) 고무 혼합물
KR102230854B1 (ko) 유기 실리카 함유 마스터 배치 탄성체 조성물
US10781302B2 (en) Rubber mixtures
JP6465559B2 (ja) ゴム組成物及び空気入りタイヤ
WO2016085143A1 (ko) 분산제를 포함하는 공역디엔계 중합체 고무 조성물
KR102289643B1 (ko) 타이어 트레드용 고무조성물
KR102037271B1 (ko) 고무배합용 유기 가황제, 이의 제조방법 및 이를 포함하는 고무배합 조성물
US7319124B2 (en) Vulcanizing agents based on organic sulphur-nitrogen compounds for unsaturated rubbers and mixtures of these
WO2021132822A1 (ko) 고무 조성물의 제조방법, 이의 방법으로 제조된 고무 조성물 및 이를 이용하여 제조된 타이어
US20250100969A1 (en) Compound, rubber blend containing the compound, vehicle tire comprising the rubber blend in at least one component, process for producing the compound, and use of the compound as an age resistor and/or antioxidant

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 2014729571

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 14369799

Country of ref document: US

ENP Entry into the national phase

Ref document number: 2015526489

Country of ref document: JP

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 2014143726

Country of ref document: RU

Kind code of ref document: A

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14729571

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE