JPH0468042A - Rubber composition - Google Patents
Rubber compositionInfo
- Publication number
- JPH0468042A JPH0468042A JP18055990A JP18055990A JPH0468042A JP H0468042 A JPH0468042 A JP H0468042A JP 18055990 A JP18055990 A JP 18055990A JP 18055990 A JP18055990 A JP 18055990A JP H0468042 A JPH0468042 A JP H0468042A
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- group
- formulas
- sulfur
- parts
- 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.)
- Pending
Links
- 229920001971 elastomer Polymers 0.000 title claims abstract description 48
- 239000005060 rubber Substances 0.000 title claims abstract description 48
- 239000000203 mixture Substances 0.000 title claims description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
- 239000011593 sulfur Substances 0.000 claims abstract description 17
- 244000043261 Hevea brasiliensis Species 0.000 claims abstract description 6
- 229920003052 natural elastomer Polymers 0.000 claims abstract description 6
- 229920001194 natural rubber Polymers 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 229920005549 butyl rubber Polymers 0.000 claims abstract description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000945 filler Substances 0.000 claims abstract description 4
- 239000004014 plasticizer Substances 0.000 claims abstract description 4
- 229920001195 polyisoprene Polymers 0.000 claims abstract description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 claims abstract description 4
- 229920001897 terpolymer Polymers 0.000 claims abstract description 4
- 239000012936 vulcanization activator Substances 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- -1 accelerator Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 6
- 238000010058 rubber compounding Methods 0.000 claims description 5
- 229920000459 Nitrile rubber Polymers 0.000 claims description 3
- 229920001084 poly(chloroprene) Polymers 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000003712 anti-aging effect Effects 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 17
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000654 additive Substances 0.000 abstract description 2
- 230000000996 additive effect Effects 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 238000013329 compounding Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000004073 vulcanization Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 3
- 150000002898 organic sulfur compounds Chemical class 0.000 description 3
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 3
- 239000004636 vulcanized rubber Substances 0.000 description 3
- HLBZWYXLQJQBKU-UHFFFAOYSA-N 4-(morpholin-4-yldisulfanyl)morpholine Chemical compound C1COCCN1SSN1CCOCC1 HLBZWYXLQJQBKU-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- ZLGORAQNGFCUFU-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-phenylpyrazol-3-amine Chemical compound NC1=CC(C=2C=CC(Cl)=CC=2)=NN1C1=CC=CC=C1 ZLGORAQNGFCUFU-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、スコーチ安定性及び耐熱性に優れたゴム材料
を製造するのに適した加硫可能なゴム組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a vulcanizable rubber composition suitable for producing a rubber material with excellent scorch stability and heat resistance.
一般にゴム材料の耐熱性を改良するためには少量の硫黄
と通常促進剤として用いるよりも多量のベンゾチアジル
スルフェンアミドのような促進剤を用いることによって
得られる。Generally, the heat resistance of rubber materials can be improved by using a small amount of sulfur and a larger amount of an accelerator such as benzothiazyl sulfenamide than is normally used as an accelerator.
しかしながら、このような系は加硫速度が早く、しかも
加硫ゴムを汚染する傾向がある。However, such systems have high vulcanization rates and also tend to contaminate the vulcanized rubber.
また、上記目的達成のため硫黄の全部または一部の置換
物として、硫黄供与体あるいはゴムと反応し得る有機硫
黄化合物を使用することも知られている。It is also known to use an organic sulfur compound capable of reacting with a sulfur donor or rubber as a substitute for all or part of sulfur in order to achieve the above object.
例えば、硫黄の不存在下でテトラチウラムジスルフィド
あるいはジチオールを用いて加硫する方法も以前から提
案されてきたか、これらはゴムの加工、成型の工程にお
いて、しばしば早期加硫やスコーチ現象か起こり易く、
またブルームの傾向を有するため常に問題とされてきた
。For example, methods of vulcanization using tetrathiuram disulfide or dithiol in the absence of sulfur have been proposed for some time;
Furthermore, it has always been considered a problem because it has a tendency to bloom.
本発明の目的は、スコーチ安定性か優れ且つ耐熱性かよ
り一層改善されたゴム材料を製造するのに適した加硫可
能なゴム組成物を提供することである。An object of the present invention is to provide a vulcanizable rubber composition suitable for producing rubber materials with excellent scorch stability and further improved heat resistance.
本発明は
（１）原料ゴムに次の一般式（１）〜（４）で表わされ
るピリジン系化合物群より選んだ少なくとも１種を、原
料ゴム１００重量部に対し０．１〜１０重量部と硫黄を
０，１〜８重量部の割合で配合してなる加硫可能なゴム
組成物であり、
Ｒ′
ＲＲ・
（ここでＲ，Ｒ’は水素原子、ハロゲン原子、アルキル
基、ニトロ基、ニトロソ基、アリール基またはアルコキ
シ基を表わす。）
（２）（１）項又は（２）項記載のゴム組成物に、更に
加硫活性剤、促進剤、充填剤、軟化剤、可塑剤、老化防
止剤等のゴム配合剤を少なくとも１種配合してなるゴム
組成物であり、
（３）原料ゴムが天然ゴム、スチレン−ブタジエン共重
合体ゴム、ポリイソプレンゴム、ニトリルゴム、クロロ
プレンゴム、ブチルゴム及びエチレン・プロピレンター
ポリマーよりなる群より選んだ少なくとも１種である前
項（１，）（２）（３）のいずれかに記載のゴム組成物
である。(1) At least one kind selected from the group of pyridine compounds represented by the following general formulas (1) to (4) is added to the raw material rubber in an amount of 0.1 to 10 parts by weight per 100 parts by weight of the raw material rubber. A vulcanizable rubber composition containing 0.1 to 8 parts by weight of sulfur, R' RR (where R, R' are a hydrogen atom, a halogen atom, an alkyl group, a nitro group, represents a nitroso group, an aryl group, or an alkoxy group.) (2) The rubber composition described in item (1) or (2) is further added with a vulcanization activator, an accelerator, a filler, a softener, a plasticizer, and an aging agent. It is a rubber composition formed by blending at least one rubber compounding agent such as an inhibitor, and (3) the raw rubber is natural rubber, styrene-butadiene copolymer rubber, polyisoprene rubber, nitrile rubber, chloroprene rubber, butyl rubber, or The rubber composition according to any one of (1,), (2), and (3) above, which is at least one member selected from the group consisting of ethylene/propylene terpolymers.
実用上早期加硫もしくはスコーチの安定なものとして、
Ｎ、Ｎ’ −ジチオジモルフォリンを配合した加硫可
能なゴム組成物については知られているか、これらの加
硫ゴム組成物はなお多くの点で改善の余地がある。As a practical early vulcanization or scorch stabilizer,
Vulcanizable rubber compositions containing N,N'-dithiodimorpholine are known, but these vulcanized rubber compositions still leave room for improvement in many respects.
Ｎ、Ｎ’ −ジチオジモルフォリンを化学式で表わす
と
又−−ｙ Ｖ−ｙ
てあり、又耐熱性加硫物か得られる超加硫促進剤として
知られているテトラチウラムジスルフィドを化学式で表
わすと、
ＮＣ５−５ＣＮ
ＣＨ３ＣＨ３
であり、いずれも本発明で用いられる上記ピリジン系化
合物である隣接した２個の硫黄原子の両端にピリジン環
か導入されたものとは異なるものである。The chemical formula for N,N'-dithiodimorpholine is --y V-y, and the chemical formula for tetrathiuram disulfide, which is known as a super vulcanization accelerator obtained from heat-resistant vulcanizates. and NC5-5CN CH3CH3, both of which are different from the pyridine-based compound used in the present invention in which a pyridine ring is introduced at both ends of two adjacent sulfur atoms.
すなわち、本発明で用いられるピリジン系化合物は、例
えば２−メルカプトピリジン、２．２′ジチオジピリジ
ン、２．２−−ジチオビス（５ニトロピリジン）、２２
″−ジチオビス（ピリジン−Ｎ−オキシド） ２−メル
カプトピリジン−Ｎ−オキシドのごときものであり、従
来加硫剤、加硫促進剤または安定剤としての作用はまっ
たく知られていなかった物である。That is, the pyridine compounds used in the present invention include, for example, 2-mercaptopyridine, 2,2'dithiodipyridine, 2,2-dithiobis(5nitropyridine), 22
``-dithiobis(pyridine-N-oxide) 2-Mercaptopyridine-N-oxide, which has not been known to act as a vulcanizing agent, vulcanization accelerator or stabilizer.
実際にゴム材料を製造する場合にはかかる加硫剤のほか
に通常のゴム配合剤として使用されている加硫活性剤、
促進剤、充填剤、軟化剤、可塑剤、老化防虫剤その他の
加工助材を一緒に用いても良く、この際通常のゴム配合
剤と一緒に混合しても、また他のすべての添加物の混合
を終了した後に練り込んでもよい。When actually manufacturing rubber materials, in addition to such vulcanizing agents, vulcanization activators, which are used as ordinary rubber compounding agents,
Accelerators, fillers, softeners, plasticizers, aging insect repellents and other processing aids may be used together, whether mixed with conventional rubber compounding agents or with all other additives. The mixture may be kneaded after the mixing of the ingredients is completed.
本発明における原料ゴムとしては、天然ゴム、スチレン
−ブタジエン共重合体ゴム、ポリイソプレンゴム、ニト
リルゴム、クロロブレンゴム、ブチルゴムおよびエチレ
ン・プロピレンターポリマ等の加硫可能なゴムあるいは
これらの混合物等が含まれる。The raw rubber used in the present invention includes natural rubber, styrene-butadiene copolymer rubber, polyisoprene rubber, nitrile rubber, chloroprene rubber, butyl rubber, vulcanizable rubber such as ethylene-propylene terpolymer, or mixtures thereof. included.
前記のごとくピリジン系化合物の原料ゴムへの配合割合
はゴム１００重量部に対し、０．１−１ｏ重量部である
が、これか０１重量部未満であると加硫剤としての効果
がなく、本発明の目的を達成することか出来ず、また１
０重量部超を添加しても、効果は飽和し、加硫剤として
の一定以上の効果か上がらず経済的でない。好適には０
２〜５．０重量部である。As mentioned above, the blending ratio of the pyridine compound to the raw rubber is 0.1-10 parts by weight per 100 parts by weight of rubber, but if it is less than 0.1 parts by weight, it will not be effective as a vulcanizing agent. The purpose of the present invention cannot be achieved, and 1
Even if more than 0 parts by weight is added, the effect will be saturated and the effect as a vulcanizing agent will not exceed a certain level, which is not economical. Preferably 0
It is 2 to 5.0 parts by weight.
ピリジン系化合物と硫黄を併用すると結合効果により更
に優れた効果か得られるが、この時使用される硫黄の量
はゴム１００重量部に対して硫黄に換算してＯ［〜８０
重量部であり、好ましくは０２〜８０重量部である。If a pyridine compound and sulfur are used in combination, an even better effect can be obtained due to the binding effect, but the amount of sulfur used at this time is O [~80
Parts by weight, preferably 02 to 80 parts by weight.
この様にピリジン系化合物に該範囲の硫黄を併用した組
成物を用いて加硫すると、とくにゴムのスコーチ安定性
か顕著に増大し、且つ耐熱性に著しく優れたゴム材料が
得られる。When a composition containing a pyridine compound and sulfur in this range is vulcanized in this manner, the scorch stability of the rubber is particularly markedly increased, and a rubber material with markedly excellent heat resistance can be obtained.
以下に実施例によって、本発明を更に具体的に説明する
か、本発明はこの実施例によって同等限定されるもので
はない。EXAMPLES The present invention will be explained in more detail below with reference to Examples, but the present invention is not limited to the same extent by these Examples.
（実施例１〜４）
天然ゴムに通常ゴム配合剤および本発明におけるピリジ
ン系化合物と硫黄の併用混合物を配合した（表中の数字
は重量部を示す）。得られた組成物を加硫処理した。(Examples 1 to 4) Natural rubber was blended with a normal rubber compounding agent and a combination mixture of a pyridine compound and sulfur according to the present invention (numbers in the table indicate parts by weight). The resulting composition was vulcanized.
加硫中レオメータ−により、その加硫性を測定し得られ
た結果を第１表に示す。レオメータ−は日本合成ゴム社
製オシレーテイングディスクレオメータ−（ＯＤＲ）を
用いた。ここてＲＭＴは加硫ゴムの架橋密度あるいはモ
ジュラスに対応する最大トルク値を、Ｔ２はトルク値か
最小トルク値より２単位上昇するまでの時間（分）を、
Ｔ２Ｏは蝉大トルク値の９０％を肖るのに要する時間（
分）である。レオメータ−のＴ２値の大なることはスコ
ーチ安定性の高いことを示している。The vulcanizability was measured using a rheometer during vulcanization, and the results are shown in Table 1. The rheometer used was an oscillating disc rheometer (ODR) manufactured by Japan Synthetic Rubber Co., Ltd. Here, RMT is the maximum torque value corresponding to the crosslinking density or modulus of the vulcanized rubber, and T2 is the time (minutes) until the torque value increases by 2 units from the minimum torque value.
T2O is the time required to reach 90% of the large torque value (
minute). A high rheometer T2 value indicates high scorch stability.
また加硫後のゴム組成物から、それぞれ試料を採取し、
試料のブローアウト性を評価した結果を第１表に示した
。In addition, samples were taken from each rubber composition after vulcanization,
Table 1 shows the results of evaluating the blowout properties of the samples.
なお、評価方法は、前記の試料についてグツドリッチ式
フレクツメーターを用い、ＡＳＴＭ Ｄ−６２３５８の
方法に準拠して行った。試料かブローアウトしたときの
ブローアウト温度を測定し、比較した。In addition, the evaluation method was performed on the above-mentioned sample using a Gudrich flexmeter in accordance with the method of ASTM D-62358. The blowout temperature when the sample was blown out was measured and compared.
（比較例１〜３）
天然ゴムに、本発明におけるピリジン系化合物を添加せ
ず、硫黄、有機硫黄化合物としてテトラメチルチウラム
ジスルフィド、及び通常の加硫促進剤より選んだ２種を
配合したものを比較例１〜３とした。特に比較例２では
、少量の硫黄と通常促進剤として用いるより多量の促進
剤を用いたものを加硫処理した。(Comparative Examples 1 to 3) Natural rubber was blended with sulfur, tetramethylthiuram disulfide as an organic sulfur compound, and two types selected from ordinary vulcanization accelerators without adding the pyridine-based compound of the present invention. Comparative Examples 1 to 3 were given. In particular, in Comparative Example 2, a vulcanization treatment was performed using a small amount of sulfur and a larger amount of accelerator than normally used as an accelerator.
加硫条件、使用したレオメータ−１測定値のＲＭＴ、Ｔ
２、Ｔ２Ｏは実施例１〜４と同しである。Vulcanization conditions, RMT of rheometer 1 measurement value used, T
2. T2O is the same as in Examples 1-4.
また加硫後のゴム組成物から、それぞれ試料を採取し、
実施例１〜４と同様の方法でブローアウト温度を測定し
た。結果を第１表に示す。In addition, samples were taken from each rubber composition after vulcanization,
The blowout temperature was measured in the same manner as in Examples 1-4. The results are shown in Table 1.
実施例１〜４の結果から明らかなように、本発明によっ
て得られるピリジン系化合物を硫黄と併用することによ
り、とくに優れたスコーチ安定性と高い架橋密度を同時
に達成でき、工業的に極めて有用なゴム材料が得られる
ことがわかる。As is clear from the results of Examples 1 to 4, by using the pyridine compound obtained by the present invention in combination with sulfur, particularly excellent scorch stability and high crosslinking density can be achieved at the same time, which is extremely useful industrially. It can be seen that a rubber material is obtained.
また本発明によって得られるピリジン系化合物を硫黄と
併用して加硫したゴム組成物は、プロアウド温度が上昇
し、耐熱性が向上した。Furthermore, the rubber composition obtained by vulcanizing the pyridine compound obtained by the present invention in combination with sulfur had an increased proaud temperature and improved heat resistance.
なお比較例１〜３では、従来の加硫剤を用いたゴム組成
物ではスコーチ安定性と耐熱性の向上が同時に得られな
いことを示す。Comparative Examples 1 to 3 show that improvements in scorch stability and heat resistance cannot be obtained at the same time with rubber compositions using conventional vulcanizing agents.
本発明のピリジン系化合物を加硫剤として得られたゴム
組成物又はピリジン系化合物と硫黄もしくは有機硫黄化
合物を併用して得られたゴム組成物は、スコーチ安定性
に優れ、耐熱性を向上したゴム組成物が得られる。A rubber composition obtained by using the pyridine compound of the present invention as a vulcanizing agent or a rubber composition obtained by using a pyridine compound in combination with sulfur or an organic sulfur compound has excellent scorch stability and improved heat resistance. A rubber composition is obtained.
Claims (3)
るピリジン系化合物群より選んだ少なくとも１種を、原
料ゴム１００重量部に対し０．１〜１０重量部と硫黄を
０．１〜８重量部の割合で配合してなる加硫可能なゴム
組成物。 ▲数式、化学式、表等があります▼（１） ▲数式、化学式、表等があります▼（２） ▲数式、化学式、表等があります▼（３） ▲数式、化学式、表等があります▼（４） （ここでＲ、Ｒ′は水素原子、ハロゲン原子、アルキル
基、ニトロ基、ニトロソ基、アリール基またはアルコキ
シ基を表わす。）(1) Add at least one kind selected from the group of pyridine compounds represented by the following general formulas (1) to (4) to the raw rubber, and add 0.1 to 10 parts by weight and 0 sulfur to 100 parts by weight of the raw rubber. A vulcanizable rubber composition blended in a proportion of .1 to 8 parts by weight. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (1) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (2) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (3) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ( 4) (Here, R and R' represent a hydrogen atom, a halogen atom, an alkyl group, a nitro group, a nitroso group, an aryl group, or an alkoxy group.)
老化防止剤等のゴム配合剤を少なくとも１種配合してな
る請求項１又は２記載のゴム組成物。(2) Vulcanization activator, accelerator, filler, softener, plasticizer,
3. The rubber composition according to claim 1, further comprising at least one rubber compounding agent such as an anti-aging agent.
合体ゴム、ポリイソプレンゴム、ニトリルゴム、クロロ
プレンゴム、ブチルゴム及びエチレン・プロピレンター
ポリマーよりなる群より選んだ少なくとも１種である請
求項１、２、３のいずれかに記載のゴム組成物。(3) The raw material rubber is at least one selected from the group consisting of natural rubber, styrene-butadiene copolymer rubber, polyisoprene rubber, nitrile rubber, chloroprene rubber, butyl rubber, and ethylene-propylene terpolymer. , 3. The rubber composition according to any one of .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18055990A JPH0468042A (en) | 1990-07-10 | 1990-07-10 | Rubber composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18055990A JPH0468042A (en) | 1990-07-10 | 1990-07-10 | Rubber composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0468042A true JPH0468042A (en) | 1992-03-03 |
Family
ID=16085399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18055990A Pending JPH0468042A (en) | 1990-07-10 | 1990-07-10 | Rubber composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0468042A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001016227A1 (en) * | 1999-08-31 | 2001-03-08 | Flexsys B.V. | Carbon black rubber coupling by mercaptopyridines |
| WO2001016226A1 (en) * | 1999-08-31 | 2001-03-08 | Flexsys B.V. | Hardness stabilization by mercaptopyridines |
| JP2009040898A (en) * | 2007-08-09 | 2009-02-26 | Toyo Tire & Rubber Co Ltd | Rubber composition for tire |
| JP2011074313A (en) * | 2009-10-01 | 2011-04-14 | Yokohama Rubber Co Ltd:The | Rubber composition, and pneumatic tire using the same |
| JP2019052235A (en) * | 2017-09-14 | 2019-04-04 | 住友化学株式会社 | Rubber composition |
| CN111094428A (en) * | 2017-09-14 | 2020-05-01 | 住友化学株式会社 | Rubber composition |
| WO2020175344A1 (en) * | 2019-02-27 | 2020-09-03 | 住友化学株式会社 | Vulcanized rubber composition |
-
1990
- 1990-07-10 JP JP18055990A patent/JPH0468042A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001016227A1 (en) * | 1999-08-31 | 2001-03-08 | Flexsys B.V. | Carbon black rubber coupling by mercaptopyridines |
| WO2001016226A1 (en) * | 1999-08-31 | 2001-03-08 | Flexsys B.V. | Hardness stabilization by mercaptopyridines |
| JP2009040898A (en) * | 2007-08-09 | 2009-02-26 | Toyo Tire & Rubber Co Ltd | Rubber composition for tire |
| JP2011074313A (en) * | 2009-10-01 | 2011-04-14 | Yokohama Rubber Co Ltd:The | Rubber composition, and pneumatic tire using the same |
| JP2019052235A (en) * | 2017-09-14 | 2019-04-04 | 住友化学株式会社 | Rubber composition |
| CN111094428A (en) * | 2017-09-14 | 2020-05-01 | 住友化学株式会社 | Rubber composition |
| WO2020175344A1 (en) * | 2019-02-27 | 2020-09-03 | 住友化学株式会社 | Vulcanized rubber composition |
| JPWO2020175344A1 (en) * | 2019-02-27 | 2020-09-03 | ||
| CN113490607A (en) * | 2019-02-27 | 2021-10-08 | 住友化学株式会社 | Vulcanized rubber composition |
| US20220119623A1 (en) * | 2019-02-27 | 2022-04-21 | Sumitomo Chemical Company, Limited | Vulcanized rubber composition |
| EP3932691A4 (en) * | 2019-02-27 | 2022-11-23 | Sumitomo Chemical Company Limited | Vulcanized rubber composition |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH04275349A (en) | Vulcanized rubber | |
| US2731442A (en) | Sulfur vulcanizable rubber stabilized with a mixture of an alkyl substituted phenol and an alkyl substituted di(hydroxyphenyl) alkane | |
| JPH0468042A (en) | Rubber composition | |
| JPS6151041A (en) | Rubber composition | |
| US3579460A (en) | Sulfenamide compositions stabilized by organic disulfides | |
| JPH0689181B2 (en) | Rubber composition | |
| US2306669A (en) | Vulcanization of rubber | |
| JPH01188541A (en) | Curing activator for non-halogenated rubber | |
| JPS5819693B2 (en) | Kairiyousareta Karyuusokushinzaikei | |
| AU594615B2 (en) | Rubber vulcanization system | |
| US4042642A (en) | Urea additives for sulfur vulcanizable polymers | |
| JPH01306442A (en) | Chloroprene rubber vulcanized composition | |
| JPS5915345B2 (en) | High hardness rubber composition | |
| WO2001016226A1 (en) | Hardness stabilization by mercaptopyridines | |
| US4595781A (en) | N,N'-dithiobisformanilides and their use in diene rubber | |
| US4080342A (en) | N-(α-alkylbenzylthio)succinimide | |
| US2947720A (en) | Oxidation products of 6-substituted-2, 2, 4-trialkyl dihydroquinolines as antioxidants | |
| US3111502A (en) | Stabilized olefin polymer compositions | |
| US3142684A (en) | Nu-(beta-cyanoethylalkyl)-2-arylenethiazole sulfenamide | |
| KR950001636B1 (en) | Rubber composition against nitro amine | |
| JPH01278543A (en) | Rubber composition | |
| JPS62100542A (en) | Vulcanizing accelerator for rubber | |
| JPH0241345A (en) | Rubber composition having improved blooming tendency | |
| JPH0480247A (en) | Halogenated butyl rubber composition | |
| JPS6327541A (en) | Rubber composition |