KR20010046857A - A rubber composition containing maleimide coupling agent - Google Patents

A rubber composition containing maleimide coupling agent Download PDF

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Publication number
KR20010046857A
KR20010046857A KR1019990050807A KR19990050807A KR20010046857A KR 20010046857 A KR20010046857 A KR 20010046857A KR 1019990050807 A KR1019990050807 A KR 1019990050807A KR 19990050807 A KR19990050807 A KR 19990050807A KR 20010046857 A KR20010046857 A KR 20010046857A
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South Korea
Prior art keywords
rubber composition
coupling agent
agent
silica
rubber
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KR1019990050807A
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Korean (ko)
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이병조
박성호
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조충환
한국타이어 주식회사
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Priority to KR1019990050807A priority Critical patent/KR20010046857A/en
Publication of KR20010046857A publication Critical patent/KR20010046857A/en

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    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
    • C08K5/353—Five-membered rings
    • 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
    • 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
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • 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
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/006—Additives being defined by their surface area

Abstract

PURPOSE: A rubber composition containing a novel maleimide coupling agent is provided, to improve the rotation resistance without the deterioration of abrasion and braking property and the environment-affinity by not containing sulfur. CONSTITUTION: The rubber composition comprises a known rubber composition for tire tread comprising rubber, 10-20 wt% of a silica reinforcing agent based on the weight of rubber, a softening agent, zinc oxide and stearic acid as a curing activator, a processing auxiliary, a curing agent and a curing promoter; and 1-40 wt% of a novel maleimide coupling agent represented by the formula 3 based on the weight of the silica reinforcing agent. Preferably the silica reinforcing agent is precipitated silica, and has the BET specific surface area of 400 m¬2/g or less and the CTAB specific surface area of 400 m¬2/g or less.

Description

신규 말레이미드 커플링제를 함유한 고무 조성물{A rubber composition containing maleimide coupling agent}A rubber composition containing maleimide coupling agent

본 발명은 신규 말레이미드 커플링제를 함유한 고무 조성물에 관한 것으로, 고분자와 반응하는 부위에 말레이미드기를 도입한 커플링제로, 마모성능 및 제동 성능을 유지하면서 회전저항을 향상시킨 신규 말레이미드 커플링제를 함유한 고무 조성물에 관한 것이다.The present invention relates to a rubber composition containing a novel maleimide coupling agent, which is a coupling agent incorporating a maleimide group in a site reacting with a polymer, wherein the novel maleimide coupling agent improves rotational resistance while maintaining wear performance and braking performance. It relates to a rubber composition containing.

최근 타이어 산업의 발전 경향은 저연비, 저회전저항 그리고 환경 친화적인 제품을 생산하는데 그 목적을 두고, 기술력을 확대하고 있다. 이러한 관심과 기술력의 발달은 초기에는 보강제로 가장 널리 사용되는 카본 블랙과 고분자와의 상호작용력의 향상에 초점이 맞춰져 왔다. 고분자의 보강제로 사용되는 카본 블랙은 고분자와 혼합하는 과정에서 카본 블랙의 특성상 쉽게 분산되지 않는 등의 문제점이 있어, 이에 대한 해결책으로 실리카 보강제를 혼합하는 방법이 제시되었다. 하지만 극성이 강한 실리카가 비극성인 고무와 쉽게 혼화되지 않아, 서로 다른 물질 사이의 결합력을 높이기 위한 커플링제가 도입되었다. 커플링제는 실리카와 고분자 간의 상호 작용력을 향상시켜, 실리카를 응용한 타이어 기술의 비약적 발전을 가져왔다. 커플링제는 할로겐, 알콕시, 아민등 쉽게 가수분해할 수 있는 작용기와, 고분자와 결합할 수 있는 작용기를 분자 내에 가지고 있는 실란 화합물로, 실란 커플러라고도 하며, 고분자의 보강제로 쓰이는 무기 충전제와의 상호작용을 화학결합으로 결합시켜, 무기 충전제의 보강성을 향상시키는 작용을 하는 것으로 알려져 있다. 초기에는 고분자 수지의 보강제로 사용된 유리섬유의 보강성을 향상시키기 위해 적용되었으나, 최근에는 그 용도가 확장되어 무기물의 표면처리, 활성물질의 고착화, 실리카를 보강제로 사용하는 타이어의 제조 등의 목적으로 사용되고 있다.Recently, the development trend of the tire industry has been expanding technology with the aim of producing low fuel consumption, low rolling resistance and environmentally friendly products. This interest and development of technology have been focused on improving the interaction between carbon black and polymer, which is the most widely used reinforcing material. Carbon black used as a polymer reinforcing agent has a problem such that it is not easily dispersed due to the characteristics of the carbon black in the process of mixing with the polymer, a solution for mixing the silica reinforcement has been proposed as a solution. However, since the highly polar silica is not easily mixed with the non-polar rubber, a coupling agent is introduced to increase the bonding force between different materials. Coupling agents improve the interaction between silica and polymers, resulting in a quantum leap in tire technology with silica. Coupling agent is a silane compound which has a functional group which can be easily hydrolyzed such as halogen, alkoxy, amine and the functional group which can bond with polymer. It is also called silane coupler, and it interacts with inorganic filler which is used as reinforcement of polymer. It is known to act to improve the reinforcement properties of the inorganic filler by binding to the chemical bonds. It was initially applied to improve the reinforcement of glass fiber used as a reinforcing agent for polymer resins, but in recent years its use has been expanded to the purpose of surface treatment of inorganic materials, solidification of active materials, and manufacture of tires using silica as reinforcing agents. Is being used.

타이어 산업에서 상용되는 커플링제로는 Si69가 그 대표적 예로 다음의 화학식 1과 같은 구조를 가지며, 고무와 결합하는 부분이 황을 포함하므로, 고무 조성물과 모노설파이드(monosulfide, S=1), 디설하이드 (disulfide, S=2), 폴리설파이드(polysulfide, 2≤S≤6)의 비교적 단단한 결합 구조를 가지나, 황 화합물에 의한 환경적 문제를 피할 수 없다는 단점이 있다.As a coupling agent commonly used in the tire industry, Si69 has a structure such as the following Chemical Formula 1, and the part to be bonded to rubber includes sulfur, so that the rubber composition, monosulfide (S = 1), and disulfide (disulfide, S = 2), polysulfide (polysulfide, 2≤S≤6) has a relatively rigid bonding structure, but there is a disadvantage that the environmental problems caused by sulfur compounds can not be avoided.

따라서, 본 발명은종래의 황을 함유하는 커플링제를 포함한 고무 조성물을 대체하고, 마모성능 및 제동 성능을 유지하면서 회전저항을 향상시키며, 황을 포함하지 않아 환경적으로도 덜 유해한, 신규 말레이미드 커플링제를 함유한 고무 조성물을 만드는 데 그 목적이 있다.Accordingly, the present invention replaces conventional rubber compositions containing sulfur-containing coupling agents, improves rotational resistance while maintaining wear and braking performance, and is a novel maleimide that does not contain sulfur and is less environmentally harmful. The purpose is to make a rubber composition containing a coupling agent.

본 발명은 원료고무와 실리카 보강제, 연화제, 가류활성제인 산화아연 및 스테아린산, 가공조제, 가황제 및 가류 촉진제로 구성된 공지의 고무 조성물에 신규한 말레이미드 커플링제를 함유한 타이어 트레드용 고무 조성물이다.The present invention relates to a tire tread rubber composition comprising a novel maleimide coupling agent in a known rubber composition composed of a raw material rubber, a silica reinforcing agent, a softener, a zinc oxide and stearic acid as vulcanizing agents, a processing aid, a vulcanizing agent and a vulcanization accelerator.

또한, 본 발명의 신규한 말레이미드 커플링제는 가수 분해되어 무기 충전제와 반응하는 알콕시기 및 고분자와 반응하는 이미드기를 포함하며, 화학식 2의 구조를 가진다.In addition, the novel maleimide coupling agent of the present invention includes an alkoxy group that is hydrolyzed to react with an inorganic filler and an imide group that reacts with a polymer, and has a structure of Formula 2.

본 발명의 고무 조성물은 신규한 말레이미드 커플링제를 실리카 보강제 대비 1 내지 40 중량% 함유하고, 실리카 보강제는 원료고무 대비 10 내지 20 중량%의 조성을 갖는다. 또한, 본 발명에서 사용한 실리카 보강제는 침강성 실리카로서, 비이티(BET) 비표면적이 400㎡/g 이하이고, 시티에이비(CTAB) 비표면적이 400㎡/g 이하이다.The rubber composition of the present invention contains a novel maleimide coupling agent 1 to 40% by weight relative to the silica reinforcing agent, and the silica reinforcing agent has a composition of 10 to 20% by weight relative to the raw material rubber. In addition, the silica reinforcing agent used in the present invention is precipitated silica, and the BET specific surface area is 400 m 2 / g or less, and the CTI specific surface area is 400 m 2 / g or less.

본 발명은 상기 신규한 말레이미드 커플링제를 함유한 타이어 트레드용 고무 조성물을 제조하고, 기존의 Si69(Degussa社, 미국) 커플링제를 응용한 고무 조성물과 물성 및 성능을 비교 시험한 것이다.The present invention is the above A rubber composition for tire treads containing a novel maleimide coupling agent was prepared, and the physical properties and performance were compared with a rubber composition using a conventional Si69 (Degussa, USA) coupling agent.

본 발명은 다음의 실시예 및 비교예를 들어 상세히 설명하지만, 이 범위로 한정하지는 않는다.The present invention will be described in detail with reference to the following Examples and Comparative Examples, but the present invention is not limited thereto.

실시예 1Example 1

표 1의 배합비와 같이 원료고무, 보강제(실리카), 연화제, 가류활성제인 산화아연 및 스테아린산, 가공조제, 가황제 및 가류 촉진제, 그리고 신규한 커플링제를 첨가하여, 밴버리 믹서에서 배합한 후, 일정온도에서 방출한다. 배합 공정을 단계별로 상세하게 나누어 설명하면 다음의 3 단계로 나눌 수 있다.As shown in Table 1, the raw material rubber, reinforcing agent (silica), softener, zinc oxide and stearic acid as vulcanizing agents, processing aids, vulcanizing agents and vulcanization accelerators, and novel coupling agents were added and mixed in a Banbury mixer. Release at temperature. When the compounding process is described in detail step by step, it can be divided into the following three steps.

⒜ 원료고무에 보강제의 2/3, 커플링제, 산화아연, 스테아린산 및 연화제를 첨가하고, 밴버리 믹서에서 혼합한 후, 160℃에서 방출한다.(2) Two-thirds of the reinforcing agent, coupling agent, zinc oxide, stearic acid and softener are added to the raw material rubber, mixed in a Banbury mixer and discharged at 160 ° C.

⒝ ⒜에서 배합된 고무에 보강제의 나머지 1/3, 커플링제, 연화제 및 가공조제를 첨가하고, 밴버리 믹서에서 혼합한 후, 160℃에서 방출한다.The remaining 1/3 of the reinforcing agent, the coupling agent, the softener and the processing aid are added to the rubber blended in IX, mixed in a Banbury mixer and then released at 160 ° C.

⒞ ⒝에서 배합된 고무에 가황제 및 가류 촉진제를 첨가하고, 밴버리 믹서에서 혼합한 후, 1분 30초 후 방출한다.The vulcanizing agent and the vulcanization accelerator are added to the rubber blended in IX, mixed in a Banbury mixer, and then released after 1 minute and 30 seconds.

상기 방법으로 제조한 고무 제품에 대하여, 마모도, 제동특성 및 회전저항지수를 측정하고, 결과를 표 2에 제시한다. 마모도(g)는 람본 마모도(Lambourn Abrasion)이고, 제동특성은 0℃ 탄젠트 델타 (Tanδ)로 나타내며, 수치가 높을수록 성능이 우수하다 하겠고, 회전저항 특성은 60℃ 탄젠트 델타(Tanδ)로 나타내며, 수치가 낮을수록 성능이 우수하다고 할 수 있다.For rubber products manufactured by the above method, the wear degree, the braking characteristics and the rolling resistance index were measured, and the results are shown in Table 2. Abrasion degree (g) is Lambbourn Abrasion, the braking characteristic is expressed as 0 ° C tan delta (Tanδ), the higher the value, the better the performance, and the rolling resistance characteristic is expressed as 60 ° C tan delta (Tanδ), The lower the value, the better the performance.

실시예 2Example 2

신규한 말레이미드 커플링제를 실리카 대비 16%로 증량하는 것을 제외하고는, 실시예 1과 동일하게 실시하여 고무 조성물을 제조하고, 배합 조성비 및 물성 측정 결과를 표 1 및 표 2에 나타낸다.A rubber composition was prepared in the same manner as in Example 1 except that the novel maleimide coupling agent was increased to 16% of silica, and the blend composition ratio and physical property measurement results are shown in Tables 1 and 2.

실시예 3Example 3

실리카 보강제의 분율을 85 중량%로 늘린 것을 제외하고는 실시예 1과 동일하게 실시하여, 고무 조성물을 제조하고, 고무 조성물의 조성비 및 물성 측정 결과를 표 1 및 표 2에 나타낸다.A rubber composition was prepared in the same manner as in Example 1 except that the fraction of the silica reinforcing agent was increased to 85 wt%, and the composition ratio and physical property measurement results of the rubber composition are shown in Tables 1 and 2.

실시예 4Example 4

실리카 보강제의 분율을 85 중량%로, 신규한 말레이미드 커플링제를 실리카 대비 16%로 증량한 것을 제외하고는, 실시예 1과 동일한 방법으로 혼합하였으며, 고무 조성물의 조성비 및 물성 특정 결과를 표 1 및 표 2에 나타낸다.The composition was mixed in the same manner as in Example 1, except that the fraction of the silica reinforcing agent was increased to 85% by weight and the novel maleimide coupling agent was increased to 16% relative to the silica. And Table 2.

혼합조성(중량부)Mixed composition (parts by weight) 실시예1Example 1 실시예2Example 2 실시예3Example 3 실시예4Example 4 비교예1Comparative Example 1 비교예2Comparative Example 2 합성고무(KBR31)Synthetic Rubber (KBR31) 3333 3333 3333 3333 3333 3333 합성고무(s-SBR)Synthetic Rubber (s-SBR) 7676 7676 7676 7676 7676 7676 실리카(Z-175Gr)Silica (Z-175Gr) 8080 8080 8585 8585 8080 8585 커플링제(Si-69)Coupling Agent (Si-69) 6.46.4 6.86.8 신규한 커플링제New Coupling Agent 6.46.4 12.812.8 6.86.8 13.613.6 연화제(A#2 Oil)Softener (A # 2 Oil) 3131 3131 3131 3131 3131 3131 산화아연Zinc oxide 33 33 33 33 33 33 스테아린산Stearic acid 22 22 22 22 22 22 가공조제Processing aid 1.51.5 1.51.5 1.51.5 1.51.5 1.51.5 1.51.5 유황brimstone 1.41.4 1.41.4 1.41.4 1.41.4 1.41.4 1.41.4 촉진제accelerant 1.71.7 1.71.7 1.71.7 1.71.7 1.71.7 1.71.7 촉진제(DPG)Accelerator (DPG) 22 22 22 22 22 22

비교예 1Comparative Example 1

종래의 고무 산업에서 가장 널리 사용하고 있는 Si-69[비스(트리에폭시실릴프로필)테트라설파이드] 커플링제를 실리카 대비 8% 사용하여 실시예 1에서와 동일한 방법으로 혼합하고, 물성 측정 결과를 표 2에 나타낸다.The Si-69 [bis (triepoxysilylpropyl) tetrasulfide] coupling agent, which is widely used in the conventional rubber industry, was mixed in the same manner as in Example 1 using 8% of silica, and the physical property measurement results are shown in Table 2 below. Shown in

비교예 2Comparative Example 2

종래의 Si-69[비스(트리에폭시실릴프로필)테트라설파이드] 커플링제를 실리카 대비 8% 사용하고, 실리카 보강제의 분율을 85 중량%로 늘린 것을 제외하고는 실시예 1에서와 동일한 방법으로 혼합하고, 물성 측정 결과를 표 2에 나타낸다.Mixing was carried out in the same manner as in Example 1 except that the conventional Si-69 [bis (triepoxysilylpropyl) tetrasulfide] coupling agent was used 8% relative to silica and the fraction of silica reinforcing agent was increased to 85% by weight. And physical property measurement results are shown in Table 2.

시험항목Test Items 실시예1Example 1 실시예2Example 2 실시예3Example 3 실시예4Example 4 비교예1Comparative Example 1 비교예2Comparative Example 2 300퍼센트 모듈러스300 percent modulus 108108 120120 135135 140140 105105 130130 신장률(%)Elongation (%) 450450 430430 425425 415415 450450 390390 마모도(g)Wear (g) 0.58710.5871 0.58200.5820 0.58710.5871 0.56570.5657 0.59570.5957 0.58740.5874 0℃ 탄젠트델타(Tanδ)0 ° C Tangent Delta (Tanδ) 0.2230.223 0.2120.212 0.2100.210 0.2000.200 0.2110.211 0.1890.189 60℃ 탄젠트 델타(Tanδ)60 ° C Tangent Delta (Tanδ) 0.1380.138 0.1350.135 0.1290.129 0.1280.128 0.1450.145 0.1390.139

표 2의 물성 측정 결과로부터, 신규한 커플링제를 사용하여 제조한 고무 조성물은, 종래의 Si-69와 같은 제품과 비교하여, 마모도는 비슷하거나 감소하는 경향을 보이고, 0℃ 탄젠트 델타(Tanδ)로 나타나는 제동특성도 비슷하거나 향상되며, 60℃ 탄젠트 델타(Tanδ)로 나타나는 회전저항은 향상된 결과를 보인다.From the measurement results of the physical properties of Table 2, rubber compositions prepared using the novel coupling agents showed a tendency of similar or decreasing wear compared to products such as Si-69, and 0 ° C tan delta (Tanδ). The braking characteristic is shown to be similar or improved, and the rotational resistance represented by 60 ° C tan delta (Tanδ) shows an improved result.

본 발명에서 제조된 신규한 말레이미드 커플링제를 함유하는 고무 조성물은 종래의 커플링제를 포함한 고무 조성물과 물성 및 성능을 비교할 때, 마모성능 및 제동성능을 유지하면서 회전 저항이 향상된 타이어를 제조할 수 있고, 타이어용 고무 조성물의 제조공정을 직접 적용가능하므로, 기존의 고무 조성물을 용이하게 대체할 수 있어 경제적이다. 또한 종래의 제품과 비교할 때, 고무 조성물에 황 화합물을 포함하지 않으므로, 타이어용 고무 조성물 전체 구성에 포함되는 황의 양이 감소되어 환경적 측면에서도 덜 유해하다는 이점이 있다.The rubber composition containing the novel maleimide coupling agent prepared in the present invention can produce a tire having improved rolling resistance while maintaining the wear performance and the braking performance when comparing the physical properties and performance with the rubber composition including the conventional coupling agent. In addition, since the manufacturing process of the rubber composition for a tire can be directly applied, it is possible to easily replace the existing rubber composition is economical. In addition, compared with conventional products, since the rubber composition does not contain a sulfur compound, there is an advantage that the amount of sulfur included in the overall composition of the rubber composition for a tire is reduced, which is less harmful in terms of environment.

Claims (4)

원료고무와 실리카 보강제, 연화제, 가류활성제인 산화아연 및 스테아린산과 가공조제, 가황제 및 가류촉진제로 구성된 공지의 타이어 트레드용 고무 조성물에 신규한 말레이미드 커플링제를 함유한 고무 조성물.A rubber composition comprising a novel maleimide coupling agent in a known rubber tread rubber composition composed of a raw material rubber, a silica reinforcing agent, a softening agent, a zinc oxide and stearic acid as vulcanizing agents, a processing aid, a vulcanizing agent and a vulcanization accelerator. 제 1항에 있어서, 신규한 말레이미드 커플링제는 화학식 3의 구조를 가지는 것을 특징으로 하는 고무 조성물.The rubber composition of claim 1, wherein the novel maleimide coupling agent has a structure of formula 3. 제 1항에 있어서, 고무 조성물은 신규한 말레이미드 커플링제를 실리카 보강제 대비 1 내지 40 중량% 함유하고, 실리카 보강제는 원료고무 대비 10 내지 20 중량%의 조성을 갖는 고무 조성물The rubber composition according to claim 1, wherein the rubber composition contains 1 to 40% by weight of the novel maleimide coupling agent relative to the silica reinforcement, and the silica reinforcement has a composition of 10 to 20% by weight relative to the raw material rubber. 제 1항에 있어서, 실리카 보강제는 침강성 실리카로서, 비이티(BET) 비표면적이 400㎡/g 이하이고, 시티에이비(CTAB) 비표면적이 400㎡/g 이하인 실리카 보강제를 혼합하는 것을 특징으로 하는 고무 조성물.The method of claim 1, wherein the silica reinforcing agent is precipitated silica, characterized by mixing a silica reinforcing agent having a BET specific surface area of 400 m 2 / g or less and a city ABB (CTAB) specific surface area of 400 m 2 / g or less. Rubber composition.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115806701A (en) * 2022-11-16 2023-03-17 宁国市赛科思橡胶有限公司 High-hardness wear-resistant durable hydrogenated nitrile rubber compound and preparation method thereof

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US3755354A (en) * 1969-05-05 1973-08-28 Gen Electric Amide acid and imido-substituted organosilanes
JPS6429385A (en) * 1987-07-27 1989-01-31 Bridgestone Corp Silane coupling agent
JPH06200015A (en) * 1992-12-28 1994-07-19 Nippon G Ii Plast Kk Production of alkoxysilylated polyphenylene ether
KR20000017571A (en) * 1998-08-26 2000-03-25 에드거 제이. 스미스 2세 Imidosilane Compositions
KR20010046856A (en) * 1999-11-16 2001-06-15 조충환 A silane coupling agent employing maleimide
KR100401394B1 (en) * 1995-03-29 2003-12-24 꽁빠니 제네랄 드 에따블리세망 미쉘린-미쉘린 에 씨 Rubber compositions for tire making based on aluminum " doped "

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Publication number Priority date Publication date Assignee Title
US3755354A (en) * 1969-05-05 1973-08-28 Gen Electric Amide acid and imido-substituted organosilanes
JPS6429385A (en) * 1987-07-27 1989-01-31 Bridgestone Corp Silane coupling agent
JPH06200015A (en) * 1992-12-28 1994-07-19 Nippon G Ii Plast Kk Production of alkoxysilylated polyphenylene ether
KR100401394B1 (en) * 1995-03-29 2003-12-24 꽁빠니 제네랄 드 에따블리세망 미쉘린-미쉘린 에 씨 Rubber compositions for tire making based on aluminum " doped "
KR20000017571A (en) * 1998-08-26 2000-03-25 에드거 제이. 스미스 2세 Imidosilane Compositions
KR20010046856A (en) * 1999-11-16 2001-06-15 조충환 A silane coupling agent employing maleimide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115806701A (en) * 2022-11-16 2023-03-17 宁国市赛科思橡胶有限公司 High-hardness wear-resistant durable hydrogenated nitrile rubber compound and preparation method thereof

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