JPS58154742A - Diene rubber composition - Google Patents
Diene rubber compositionInfo
- Publication number
- JPS58154742A JPS58154742A JP3673482A JP3673482A JPS58154742A JP S58154742 A JPS58154742 A JP S58154742A JP 3673482 A JP3673482 A JP 3673482A JP 3673482 A JP3673482 A JP 3673482A JP S58154742 A JPS58154742 A JP S58154742A
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- diene
- amino group
- rubber composition
- weight
- 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.)
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Abstract
Description
【発明の詳細な説明】 長性）が改良されたジエン系ゴム組成物に関する。[Detailed description of the invention] The present invention relates to a diene rubber composition with improved durability.
一すイソデレンゴム（ＩＲ）、ポリブタジェンゴム（Ｂ
Ｒ）、スチレンブタジェンゴム（ＳＢＲ）に代表される
曾成ゴムにタイヤ用途、防振ゴム用途をはじめとして各
種工業用途に巾広く用いられている。Isodelene rubber (IR), polybutadiene rubber (B
R), styrene-butadiene rubber (SBR) is widely used in various industrial applications, including tire applications and anti-vibration rubber applications.
例えば高シスＢＲＦｉ耐屈曲性に優れかつエネルギーロ
スか少ないためタイヤ用途に好適でるり、８ＢＲは加工
性、破壊特性が良好なため、タイヤ、ハキモノ、防振用
途など各種工業用に広く用いられている。更に高シス！
Ｒは良好な加工性を持ち、耐屈曲性、破壊特性に優れて
いるという特許を活かしトランク、パス等の鳥負葡用タ
イヤに用いられている。For example, high-cis BRFi has excellent bending resistance and low energy loss, making it suitable for tire applications, while 8BR has good workability and fracture properties, so it is widely used in various industrial applications such as tires, footwear, and anti-vibration applications. There is. Even higher sis!
R has good workability and is used in tires for trunks, passes, etc., taking advantage of its patented properties of excellent bending resistance and fracture properties.
しかしながら、昨今のタイヤのラジアル化、験ｆ等に対
する厳しい環境規制からゴム工業界からのゴム材料に対
する要求は複雑多様化して米でおり従来の合成ゴムに対
して１１４１性の改良か強く望まれている。特に耐亀裂
成長性の改良かＷＩＬまれている。この特性はゴム材料
の疲労時性を示すものでめＶ極めて１賛な特性である。However, due to the recent shift to radial tires and strict environmental regulations regarding test f, etc., the requirements for rubber materials from the rubber industry have become more complex and diverse, and there is a strong desire for improved 1141 properties compared to conventional synthetic rubber. There is. WIL is particularly focused on improving crack growth resistance. This characteristic indicates the fatigue resistance of the rubber material and is an extremely favorable characteristic.
本尭明者らにこれらの４１求に応えるべく種々の検討を
行ったところ、一定量の第三級のアミノ基を含有する化
合−を導入してなるジエン系重合体ゴムを含むゴム組成
物が弓；張強さなどの加硫物性を低下させることなく耐
亀裂成長性に優れていることを見出し本発明に到運した
。After conducting various studies to meet these 41 requests, the present researchers discovered that a rubber composition containing a diene-based polymer rubber containing a certain amount of a compound containing a tertiary amino group was introduced. The inventors have discovered that the vulcanized material has excellent crack growth resistance without deteriorating the vulcanized physical properties such as tensile strength and the like, leading to the present invention.
すなわち本発明に、共役ジオレフィンあるいに共役ジオ
レフィンとビニル置換芳香族炭化水素ｖ１曾して得られ
たポリマーであって／ リマー鎖中に第三級のアミノ基
を有する化合＠を１１〜３０重１１％導入してなるジエ
ン系１ｆ ｌ ｔｔ体ゴムを少なくとも１０１を憾含有
物を提供することにある。That is, in the present invention, a conjugated diolefin or a polymer obtained by combining a conjugated diolefin and a vinyl-substituted aromatic hydrocarbon v1/compounds having a tertiary amino group in the remer chain 11- The object of the present invention is to provide a diene-based 1F l tt body rubber containing at least 101% by weight of 30% by weight.
本発明のゴム組成物の優れた物性は一定量の第三級アミ
ン基を有する化＠物を導入してなる、ジエン系重合体ゴ
ムを用いることによって得られる。該ジエン系１曾体ゴ
ムに天然ゴム（ＮＲ）、ＩＲ，ＢＲ，８ＢＲ，アクリロ
ニトリルフタジエンゴム（ＮＢＲ）、エテレンーグロピ
レンゴム（ＥＰＲ）、ブチルゴム（ＩＩＲ）から選ばれ
た１棟又は２′ｊａ以上のジエン系ゴムと配合はれる。The excellent physical properties of the rubber composition of the present invention are obtained by using a diene polymer rubber into which a certain amount of a compound having a tertiary amine group is introduced. One or two bases selected from natural rubber (NR), IR, BR, 8BR, acrylonitrile phtadiene rubber (NBR), ethylene-glopyrene rubber (EPR), and butyl rubber (IIR) as the diene-based monomer rubber. It can be blended with diene rubber of ja or more.
このうちＳＢＲ，ＢＲ，ＩＲ。Among these, SBR, BR, and IR.
ＮＲ％ＮＢＲがより好ましい。NR%NBR is more preferred.
本発明のゴム組成物において、第三級アミノ基を有する
化付物を導入してなるジエン系１台体ゴムの含有量は少
なくとも１０重量鳴、好ましくＦｉ２０重量嚢以上必要
で、１０重量嘔未満でに目的とする物性、特に耐亀裂成
長性に得られない。又該ジエン系重合体ゴム単味使用で
は加工性に劣るなど好ましくない面がでるので９５重ｆ
暢を越えわことが好愛しい。In the rubber composition of the present invention, the content of the diene-based monolithic rubber into which a compound having a tertiary amino group has been introduced is at least 10% by weight, preferably 20% by weight or more, and less than 10% by weight. However, the desired physical properties, especially crack growth resistance, cannot be obtained. Also, if the diene-based polymer rubber is used alone, there will be undesirable aspects such as poor processability, so 95 weight f
I love that it's beyond simple.
＋ｉ明Ｖこおいて共役ジオレフィン又はこれとビニル置
換芳香族炭化水素の重付形態に既知の方法で通常の条件
により、例えばラジカル発生剤を用いての懸濁ｌ曾、塊
状重付、乳化組合、有機アルカリ金ｌ１４ｖ用いてのア
ニオン１甘などがあるか、レドックス触媒による乳化］
Ｉ曾あるいは有機リチウム開始剤によるアニオン重曾が
好適である。In this case, the conjugated diolefin or the polymerized form of the conjugated diolefin and the vinyl-substituted aromatic hydrocarbon are treated in a known manner and under conventional conditions, such as suspension using a radical generator, bulk loading, emulsification. Emulsification by redox catalyst, whether there is anion 1 sweetness using organic alkali gold 14v, etc.]
Anionic or heavy initiators with organolithium initiators are preferred.
本発明に用いられる共役ジオレフィンとしでにブタジェ
ン、イソプレン、ペンタジェンなどが挙げられまたビニ
ル置換芳香族炭化水素としてスチレン、α−メチルスチ
レンナトが挙げられる。Conjugated diolefins used in the present invention include butadiene, isoprene, pentadiene, etc., and vinyl-substituted aromatic hydrocarbons include styrene and α-methylstyrene.
ジエン系１曾体ゴムの分子鎖中への第三級アばノ基を有
する化付物の導入に、例えば共役ジオレフィン又はこれ
とビニル芳香族炭化水素及び第三級アミノ基を有する化
付物の共貞せにより行われる。For the introduction of a compound having a tertiary abano group into the molecular chain of a diene-based monomer rubber, for example, a conjugated diolefin or a compound having a vinyl aromatic hydrocarbon and a tertiary amino group can be used. It is carried out through mutual chastity of things.
第三級アゼノ基含有化付物としては、例えば一般式
（式中Ｒ１及びＲ，ｔｉｅ、〜Ｃ１ａのアルキル基、ア
ラルキル基、了り一ル基）で示される核置換スチレン前
導体、たとえばジメチルアミンエチルスチレン、ジエチ
ルアミノエテルスチレン、ジエチルアミノエテルスチレ
ン、ジオクチルアばノエチルステレン、ジ２−エチルへ
キシルアミノエテルスチレン、ジオクタデシルアミノエ
テルスチレンなどヵ１用いられる。これらの他にｊ！に
、朔えば２−ビニルピリジン、４−ビニルピリジン、ジ
メテルアεノエデルアクリレート、ジエチルアミノエチ
ルアクリレート、ジオクチルアミノエチルアクリレート
などが挙げられる。符に核曾換スナレ／銹導体が好！し
い。Examples of tertiary azeno group-containing adducts include nuclear-substituted styrene precursors represented by the general formula (in which R1 and R, tie, ~C1a are alkyl groups, aralkyl groups, and monoyl groups), such as dimethyl Amine ethyl styrene, diethylamino ester styrene, diethylamino ester styrene, dioctyl abano ethyl sterene, di-2-ethylhexylamino ester styrene, dioctadecylamino ester styrene and the like are used. Besides these j! Examples include 2-vinylpyridine, 4-vinylpyridine, dimethylacrylate, diethylaminoethyl acrylate, and dioctylaminoethyl acrylate. I like the nuclear change to the sign / the conductor! Yes.
本発明のジエン系重曾体ゴム中の第三級アミノ基を有す
る化付物の含有量は１〜３０重櫨嘔、好！シクに２〜２
０重量囁の範囲にある。ｌｌ菫嘔未満であると本＠明の
目的とする物性が得られず、また、３０重重量上越える
と引彊特性弗の加（ｉｌＥ物性が低下する。The content of adducts having a tertiary amino group in the diene-based heavy rubber of the present invention is 1 to 30, preferably! 2 to 2 in a row
It is in the range of 0 weight whisper. If the weight is less than 11 weight, the physical properties aimed at in the present invention cannot be obtained, and if the weight exceeds 30 weight, the drag properties will be increased (the physical properties will deteriorate).
本発明のジエン系重合体ゴムの分子量は特ｌＯ〜１５０
の範曲にあることか好ましい。The molecular weight of the diene polymer rubber of the present invention is from 10 to 150.
It is preferable that it be in the range of .
ムーニーか１０より小さいと加工時のコールドフロー等
が問題となり、又ムーニーが１５０より大きいと加工す
るのが困難である。If the Mooney value is less than 10, cold flow during processing will become a problem, and if the Mooney value is greater than 150, processing will be difficult.
不発−の第三級アミノ基で修飾された共重せ体ゴムは４
１７ ｗ−の種類や重付方法によって７Ｘｌ値ゴムの耐
亀裂成長性の数置効果に大きな差がないが、％に有機リ
ブラム開始剤を用いて得られたスチレン／ブタジェン系
ゴム、スチレン／イソプレン系ゴムでは未加硫ゴムの強
度も同時に改良されるという利点がある。The copolymer rubber modified with unexploded tertiary amino groups is 4
17 There is no significant difference in the numerical effect of crack growth resistance of 7Xl value rubber depending on the type of w- or weighting method, but styrene/butadiene rubber obtained using an organic Ribram initiator and styrene/isoprene The advantage of this type of rubber is that it also improves the strength of unvulcanized rubber.
本＃５明のジエン系ゴム組成物はＴＢ等の加４に物性か
損われずに耐亀裂成長性が改良され、疲労轡命か永くな
るのでタイヤ用途、防振用途を始めとして各樵工業用途
に好適である。The diene rubber composition of #5 Ming has improved crack growth resistance without impairing its physical properties in addition to TB etc., and has a longer fatigue life, so it can be used in various woodworking industries including tire applications and anti-vibration applications. Suitable for this purpose.
次に実施例により本発明な史に具体的に説明するが、不
発Ｆ！＃はその景旨な越えない限り以下の実施例に制約
されるものでにない。Next, the history of the present invention will be specifically explained using examples. # is not restricted to the following embodiments unless the purpose is exceeded.
実施例−１〜１１．比較例−１〜８
第１表の七ツマー組成で乳化剤としてロジン酸のカリ９
ム塩、触媒として有機過酸化物と還元剤とからなるレド
ックス系触媒を用い、乳化重台を実施した。重付温度は
７℃とし約６０囁のコンバージョンで反応を停止し、フ
ェノール系老化防止剤を加え、七ツマー除去後、ポリマ
ーを凝固乾燥した。得られたポリマー中の第三級アイ７
基を有する化合物の結付ｊｌｌは４リマーを一旦溶解し
メタノールで再沈精製したサンプルのＮＭＲ測定で求め
た。Examples-1 to 11. Comparative Examples-1 to 8 Potassium 9 of rosin acid as an emulsifier with the seven-mer composition shown in Table 1.
Emulsification was carried out using a redox catalyst consisting of an organic peroxide and a reducing agent as a catalyst. The weighting temperature was set at 7° C., and the reaction was stopped at a conversion rate of about 60 hiss. A phenolic anti-aging agent was added, and after removal of the 7-mer, the polymer was coagulated and dried. Tertiary eye 7 in the obtained polymer
The binding of the compound having the group Jll was determined by NMR measurement of a sample in which the 4-limer was once dissolved and purified by reprecipitation with methanol.
＠１表に得られたぼりマーの分析結果を示した。Table @1 shows the analysis results of the obtained streamers.
次に＠２表の配合処方で配付物を調製し、１４５℃−２
０分の条件で加＊Ｖ行った。Next, prepare a handout using the formulation shown in Table @2, and heat it to 145℃-2.
Add*V was performed under the condition of 0 minutes.
得られた物性結果を１ｇ３表に示した。The obtained physical property results are shown in the 1g3 table.
第２表
配合処方
ｌリマー １００ 重量部カーダ
ンブラック（ｉｉＡＦ） ５０ ＃亜
鉛華 ３Ｉステアリン酸
２ ′老化藺止Ｍ
１ ′（ツクラック５ｔｏａＡ）”
加硫促進剤
アクセルＭ８ム” ０５４ ・＃
ＤＭ” ０．２１ ＃硫黄 １
．５
ａｌ）Ｎ−フェニル−Ｎ’ −イノグ四ピルーｐ−フェ
ニレンジアミン
冨） Ｎ−オΦシジエチレンー２−ペンツチアジルスル
フェンアント
Ｓ）ジペンゾチアジルジスルフイド
第３表の結果から本発明のプ五組成である実施例−１〜
１１は第三級アミノ基を有する化合物を導入したジエン
系重合体ｆムを含まない比較例−ＩＫ＃べて耐亀袈成長
性に優れている。塘九第三級アずノ基を有する化合物結
合量の少ないツエン系重合体プムを用い友比較例−１，
２，６は耐亀豐成畏ＩｋＯ改嵐効果が小さい、を九第三
級７２ノ基を有す為化合物Ｏ結合量が多いジエン系重合
体ｔムを用いた比較例−３，４，７は〒１の低下が大暑
〈物性的に好ましくない。Table 2 Compounding prescription l Rimmer 100 parts by weight Cardan black (iiAF) 50 #Zinc white 3I stearic acid
2' Anti-aging M
1' (Tsukurak 5toaA) "Vulcanization accelerator accelerator M8" 054 ・#
DM” 0.21 #Sulfur 1
．． 5 al) N-phenyl-N'-inog tetrapyrrup-p-phenylenediamine concentration) N-ophiethylene-2-penzthiazylsulfenant S) dipenzothiazyl disulfide Based on the results in Table 3, the present invention Example-1~ with five compositions of
No. 11 is a diene polymer containing a compound having a tertiary amino group. Comparative example IK# does not contain a compound having a tertiary amino group. Comparative Example-1 using Tsuene-based polymer PUM with a small amount of compound bonding having a tertiary azuno group
Comparative examples 3, 4, and 2, which use diene-based polymers with a large amount of compound O bonds because they have tertiary 72 groups, have a small IkO reforming effect. 7 is a drop in 〒1, which is very hot (physical properties are not favorable).
又第三級アミノ基を有する化合物を導入し九ジエン系重
合体ゴムの含有量が少ない比較例−５では耐亀表成長性
が改嵐されない。Moreover, in Comparative Example 5, in which a compound having a tertiary amino group was introduced and the content of nine diene polymer rubber was small, the surface growth resistance was not improved.
実施例１２〜２４、比較例９〜１７、
第４表の七ツマー組威で触厳として有機リチウム−始剤
を用いて重合を行つ九。Examples 12 to 24, Comparative Examples 9 to 17, and 9 in which polymerization was carried out using an organic lithium initiator in accordance with the method shown in Table 4.
窒素置換したｓＩ反応器にシクロへ午サンを２ＳＯＯｊ
、−％／ママ−５ｏｏｙ仕込み、ノルマルプチルリチク
ムを００５〜ｏ ｏ ＩＩ ＰＨＭ添加し、反応器内Ｏ
温度を５０〜６０℃にコントロールし重合を実施した。Add 2SOO of cyclohexane to the nitrogen-substituted sI reactor.
, -%/mama-5ooy preparation, n-butyrrhizicum was added at 005~o o II PHM, and O inside the reactor was
Polymerization was carried out while controlling the temperature at 50 to 60°C.
反応転化率がほぼ１００１Ｇになつ九ら、２゜６−ジー
ｔ−ブチル−ｐ−クレゾールを加え反応を停止し九。そ
の後、脱溶乾燥しポリマーを得え、得られ九／ リマ−
の分析結果を第４表に示した。When the reaction conversion reached approximately 1001 G, 2°6-di-t-butyl-p-cresol was added to stop the reaction. After that, the polymer is obtained by removing the solution and drying.
The analysis results are shown in Table 4.
実施例−１と同様の方法で配合・加愼を行ない、第５．
６表の物性結果を得九。Blending and processing were carried out in the same manner as in Example-1, and the fifth.
The physical property results shown in Table 6 were obtained.
１８６表
注１） は１１１３表ｏａ＋）Ｋ準じ比較例−１５を１
００として表わし友。Table 186 Note 1) Comparative example-15 according to Table 1113 oa+)K 1
Friend represented as 00.
２） 比較例−１６Ｔ３）
比較例−１７１４ンは菖３表の注５）
と同じ。2) Comparative example-16T3)
Comparative example - 1714n is iris 3 table note 5)
Same as.
第５．６真の結果から本発明のゴム組成物である実施例
−１２〜１８は８１１１１００１Ｇの比較例−１２に比
べて耐亀訣成長性において優れている。5.6 From the results, Examples 12 to 18, which are the rubber compositions of the present invention, are superior to Comparative Example 12 of 81111001G in terms of grain growth resistance.
第三級ア建ノ基を有する化會物締會量の少ないジエン系
重合体ゴムを眉いえ比較例−９又はジエン重重金体シム
の含有量Ｏ／）１にい比較例−１１では耐亀豐成長性の
改嵐効果がなく、又第三級アオノ基を有する化會物紬會
量が多いジエン系重合体が五を用い友比較例−１０では
Ｔ１の低下が大暑〈好壕しくない。In Comparative Example-9 or Comparative Example-11, the diene-based polymer rubber with a small amount of compound binding having a tertiary adenyl group was In Comparative Example 10, a diene polymer which does not have the effect of improving growth properties and has a large amount of chemical compounds having a tertiary aono group is used, and the T1 decreases significantly. do not have.
又本発明のゴム組成物である実施例−１９〜２２は、比
較例−１５に較べ耐亀袈成長性に優れ、又未加硫ゴム強
直が改ｊＬ−Ｊれている。In addition, Examples 19 to 22, which are the rubber compositions of the present invention, have superior wall growth resistance compared to Comparative Example 15, and have improved unvulcanized rubber stiffness.
比較例−１３では耐亀表成長性が改嵐されておらず、比
＠９４−１４ではＴ１が大きく低下する。実施例−２３
は比較例−１６に比べて、実施例−２４は比較例−１７
に比べてそれぞれ耐亀袈成長性に優れている。In Comparative Example-13, the surface growth resistance was not modified, and T1 was significantly reduced at the ratio @94-14. Example-23
is compared to Comparative Example-16, and Example-24 is compared to Comparative Example-17.
Each has excellent resistance to turtle growth compared to the other.
Claims (3)
とビニル置換芳香族炭化水素を重合して得られた４リマ
ーであって４リマー鎖中に第三級アミノ基を有する化合
物を１〜３０重量鳴導入してなるジエン系重合体ゴムを
少なくと４１０重量重量前する疲労特性の改良きれたジ
エン系ゴム組成物。(1) Conjugated diolefin - is a 4-limer obtained by polymerizing a conjugated diolefin and a vinyl-substituted aromatic hydrocarbon, and is a compound having a tertiary amino group in the 4-limer chain of 1 to 30% by weight. A diene rubber composition having improved fatigue properties, which contains at least 410% by weight of a diene polymer rubber.
を用いて得られたものである、特許請求の範囲＠１墳配
域のジエン系ゴム組成物。(2) A diene rubber composition according to claim 1, wherein the M diene polymer rubber is obtained using an organolithium initiator.
ラルキ項記載のジエン系ゴム組成物。(3) A compound having a [tertiary a(] group) (R1, RmFiCl to C@@f), a diene-based rubber composition as described in the aralkyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3673482A JPS58154742A (en) | 1982-03-09 | 1982-03-09 | Diene rubber composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3673482A JPS58154742A (en) | 1982-03-09 | 1982-03-09 | Diene rubber composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58154742A true JPS58154742A (en) | 1983-09-14 |
| JPH0229098B2 JPH0229098B2 (en) | 1990-06-27 |
Family
ID=12477959
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3673482A Granted JPS58154742A (en) | 1982-03-09 | 1982-03-09 | Diene rubber composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58154742A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6422940A (en) * | 1987-07-17 | 1989-01-25 | Japan Synthetic Rubber Co Ltd | Rubber composition |
| JPH01101344A (en) * | 1987-10-14 | 1989-04-19 | Bridgestone Corp | Tire |
| US4835216A (en) * | 1986-11-07 | 1989-05-30 | Bridgestone Corporation | Conjugated diene series rubber compositions |
| JPH0255747A (en) * | 1988-08-22 | 1990-02-26 | Bridgestone Corp | Rubber composition |
| JPH0782422A (en) * | 1993-09-10 | 1995-03-28 | Bridgestone Corp | Rubber composition |
| WO1997019966A1 (en) * | 1995-11-28 | 1997-06-05 | Nippon Zeon Co., Ltd. | Diene rubber |
| US6362272B1 (en) | 1998-10-07 | 2002-03-26 | Jsr Corporation | Oil extended rubber and rubber composition |
| JP2010116545A (en) * | 2008-10-16 | 2010-05-27 | Sumitomo Rubber Ind Ltd | Polymer, rubber composition and tire using the same |
| JP2010116546A (en) * | 2008-10-16 | 2010-05-27 | Sumitomo Rubber Ind Ltd | Rubber composition and tire |
| WO2013002234A1 (en) * | 2011-06-28 | 2013-01-03 | 住友ゴム工業株式会社 | Rubber composition for tire and pneumatic tire |
| CN107743498A (en) * | 2015-04-10 | 2018-02-27 | 西索斯公司 | Initiator for the combined polymerization of diene monomers and vinyl aromatic monomers |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5734106A (en) * | 1980-08-08 | 1982-02-24 | Asahi Chem Ind Co Ltd | Nitrogen-containing copolymer, its production, paint comprising same and formation of film |
-
1982
- 1982-03-09 JP JP3673482A patent/JPS58154742A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5734106A (en) * | 1980-08-08 | 1982-02-24 | Asahi Chem Ind Co Ltd | Nitrogen-containing copolymer, its production, paint comprising same and formation of film |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4835216A (en) * | 1986-11-07 | 1989-05-30 | Bridgestone Corporation | Conjugated diene series rubber compositions |
| JPS6422940A (en) * | 1987-07-17 | 1989-01-25 | Japan Synthetic Rubber Co Ltd | Rubber composition |
| JPH01101344A (en) * | 1987-10-14 | 1989-04-19 | Bridgestone Corp | Tire |
| JPH0255747A (en) * | 1988-08-22 | 1990-02-26 | Bridgestone Corp | Rubber composition |
| JPH0782422A (en) * | 1993-09-10 | 1995-03-28 | Bridgestone Corp | Rubber composition |
| WO1997019966A1 (en) * | 1995-11-28 | 1997-06-05 | Nippon Zeon Co., Ltd. | Diene rubber |
| US6211321B1 (en) * | 1995-11-28 | 2001-04-03 | Nippon Zeon Co., Ltd. | Diene rubber |
| US6362272B1 (en) | 1998-10-07 | 2002-03-26 | Jsr Corporation | Oil extended rubber and rubber composition |
| JP2010116545A (en) * | 2008-10-16 | 2010-05-27 | Sumitomo Rubber Ind Ltd | Polymer, rubber composition and tire using the same |
| JP2010116546A (en) * | 2008-10-16 | 2010-05-27 | Sumitomo Rubber Ind Ltd | Rubber composition and tire |
| CN101724127A (en) * | 2008-10-16 | 2010-06-09 | 住友橡胶工业株式会社 | Polymer, rubber composition and tire using the same |
| EP2177562A3 (en) * | 2008-10-16 | 2010-08-04 | Sumitomo Rubber Industries, Ltd. | Polymer, rubber composition and tire using the same |
| EP2184318A3 (en) * | 2008-10-16 | 2010-08-04 | Sumitomo Rubber Industries, Ltd. | Rubber composition and tire |
| WO2013002234A1 (en) * | 2011-06-28 | 2013-01-03 | 住友ゴム工業株式会社 | Rubber composition for tire and pneumatic tire |
| CN107743498A (en) * | 2015-04-10 | 2018-02-27 | 西索斯公司 | Initiator for the combined polymerization of diene monomers and vinyl aromatic monomers |
| CN107743498B (en) * | 2015-04-10 | 2020-04-28 | 西索斯公司 | Initiator for copolymerization of diene monomer and vinyl aromatic monomer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0229098B2 (en) | 1990-06-27 |
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