JPS6136536B2 - - Google Patents
Info
- Publication number
- JPS6136536B2 JPS6136536B2 JP5552578A JP5552578A JPS6136536B2 JP S6136536 B2 JPS6136536 B2 JP S6136536B2 JP 5552578 A JP5552578 A JP 5552578A JP 5552578 A JP5552578 A JP 5552578A JP S6136536 B2 JPS6136536 B2 JP S6136536B2
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- diene polymer
- cyclized product
- modulus
- 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.)
- Expired
Links
- 229920001971 elastomer Polymers 0.000 claims description 32
- 239000005060 rubber Substances 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 20
- 150000001993 dienes Chemical class 0.000 claims description 17
- 238000007363 ring formation reaction Methods 0.000 claims description 14
- 229920000181 Ethylene propylene rubber Polymers 0.000 claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 244000043261 Hevea brasiliensis Species 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229920003052 natural elastomer Polymers 0.000 description 8
- 229920001194 natural rubber Polymers 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000004636 vulcanized rubber Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 230000003712 anti-aging effect Effects 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 229920003051 synthetic elastomer Polymers 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011951 cationic catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 1
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- -1 vulcanizing aids Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明はエチレン−プロピレン系ゴムに環化率
50％以上のジエン系重合体環化物をブレンドした
ゴム組成物に関し、その目的とする所は加工性が
良好で且つその加硫物が高い弾性率を有するゴム
組成物を得んとするにある。
最近、一般に汎用されている加硫ゴムに対し、
より高弾性率の加硫ゴム（従来の100％モジユラ
ス値の1.5〜２倍以上）が特定の分野において望
まれるようになつてきた。勿論この場合モジユラ
ス以外のゴム物性は従来の加硫ゴムと同程度を保
持し加工性も良好であることが望ましい。
一般に高弾性率のゴム組成物を得る方法として
は、ゴムに配合するカーボンブラツクに量を多く
したり、硫黄量を多くして架橋密度を上げる方法
等があるが、これらの方法ではゴム組成物の製造
の作業性あるいは得られた加硫ゴム組成物の物
性、加工性などが問題となり望ましいゴム組成物
を得ることは難しかつた。
また、ゴムに樹脂をブレンドしてモジユラスを
上げる方法が知られているがこの方法では加工性
が問題となる。
本発明者等はこのように加工性が優れ、加硫物
性を低下させないで且つ高弾性率を有するゴム組
成物を得んとして種々検討した結果、エチレン−
プロピレン系ゴムと50％以上の環化率を有するジ
エン系重合体とをブレンドすることにより、全く
意外にも上記目的を満足する結果を得、本発明を
完成した。
従来、天然ゴムに環化天然ゴムをブレンドする
事は知られているが、この混合物のモジユラス値
は十分ではなかつた。このブレンドにおいて高モ
ジユラス値を得るには、環化天然ゴムのブレンド
量を多くすれば一応目的は達成されるが、増量す
るにつれて引張強度が大きく低下し、本発明の意
図する所より大きく外れる結果となつている。
即ち本発明はエチレン−プロピレン系ゴム100
重量部と環化率50％以上のジエン系重合体環化物
10〜80重量部とから成るゴム組成物である。
以下に本発明を詳細に説明する。
本発明に使用されるエチレン−プロピレン系ゴ
ム（以下EP系ゴムと略称する）はエチレン及び
プロピレンの二元共重合体、エチレン−プロピレ
ンと不飽和成分との多元共重合体を含むゴム状重
合体である。ゴム中のエチレン含量は40〜80重量
％、プロピレン含量は60〜20重量％であり、不飽
和成分含量は０〜20重量％である。不飽和成分と
してはエチリデンノルボルネン、ジシクロペンタ
ジエン、１・４−ヘキサジエン、シクロオクタジ
エン等が用いられる。またジエン系重合体環化物
は天然ゴム、ポリイソプレン、ポリブタジエン、
SBR等のジエン系重合体に公知のカチオン触媒を
作用して得られる。通常ジエン系ゴムの溶液また
は水性分散体にカチオン試剤を触媒として添加さ
せる事により得られる。ジエン系重合体環化物の
環化率は50％以上、好ましくは60％以上である。
ジエン系重合体環化物の環化率が50％以上必要
であることは、EP系ゴムにブレンドした場合、
本発明の目的とする高弾性率を有するゴムを得る
ためであり、これ以下の環化率では目的を達する
ことができない。
EP系ゴムとジエン系重合体環化物のブレンド
は溶液または乳液、ロールまたはバンバリーミキ
サーで行なう事ができ、溶液でブレンドした場合
はポリマー回収法として、スチームストリツピン
グ法や、非溶剤による共沈澱法、直接脱溶剤法な
どが用いられる。又乳液の場合は、通常ジエン系
重合体乳化物の凝固法を用いることができる。
ブレンドの比率はEP系ゴム100重量部に対し、
ジエン系重合体環化物10〜80重量部、好ましくは
15〜60重量部である。10重量部より少ないとモジ
ユラス値が十分高いとは言えず、また80重量部以
上では加硫物の物性、例えば耐屈曲性、スキツド
抵抗等が悪くなる。
EP系ゴム以外の例えばシス−１・４−ポリブ
タジエンゴム（BR）、シス−１・４−ポリイソプ
レンゴム（IR）を用い、ジエン系重合体環化物
をブレンドしても十分高いモジユラス値が得られ
ない。また環化物としても実施例で詳細に述べる
ようなジエン系重合体、例えばIR、BR、NR（天
然ゴム）、SBR等の環化物でないとEP系ゴムにブ
レンドしても本発明の目的は達成されない。しか
もこれらジエン系重合体環化物の環化率が上述の
如く50％以上である必要がある。
本発明においてはEP系ゴム−ジエン系重合体
環化物ブレンド物に対し、通常ゴムに配合される
公知の添加剤が添加される。添加剤としては加硫
剤、加硫助剤、顔料、充填剤、軟化剤、老化防止
剤、分散剤などが用いられる。
本発明のゴム組成物は配合ゴムムーニー粘度が
100以下と加工性が良好であり、また加硫物は通
常100％モジユラスが60〜200Kg/cm2、引張り強度
150Kg/cm2以上、伸び100％以上のものが得られ、
従つてタイヤ、防振ゴム、バンパー、ベルト、フ
レキシブルジヨイント、カイドローラー、防舷
材、ホース、パツキング材、シーリング材等で特
に高弾性率を必要とする部分に有用である。
次に本発明を実施例及び比較例により更に具体
的に説明する。
環化物製造例
() IR環化物製造法
イソプレンゴム（日本合成ゴム社製JSR IR
2200）100ｇをトルエン３に溶かし、
BF3AcOHのエチレンジクロライド溶液（１M/
）40mlを加えて、60℃、３時間反応させた
後、少量の老化防止剤を含む大量のメタノール
中にあけて凝固させた。凝固物は50℃で一晩真
空乾燥した。環化率は88％であつた。（環化率
）
() BR環化物製造法
ブタジエンゴム（日本合成ゴム社製JSR BR
01）100ｇをキシレン13に溶かし、ベンジル
クロライドのキシレン溶液（１M/）20ml及
びAlEtCl2のキシレン溶液（１M/）30mlを加
えて44℃、30分反応させた後、少量の老化防止
剤を含む大量のメタノール中にあけて凝固させ
た。凝固物は50℃で一晩真空乾燥した。環化率
は80％であつた（環化率）
() 天然ゴム環化物製造法
市販品NR環化物（精工化学社製サーモライ
トＰ、環化率70％）を用いた。（環化物）
実施例１〜４、比較例１〜３
EP系ゴムとして日本合成ゴム社製JSR EP・33
（不飽和成分としてエチリデンノルボルネルを含
有、ムーニー値45、エチレン／プロピレン＝57／
43、ヨウ素価26）を用い、その所定量と第１表記
載量の環化物を約20倍量のトルエンに溶かし、よ
く撹拌混合した後少量の老化防止剤を含む大量の
メタノールにあけて凝固させ、50℃で一晩真空乾
燥した。
EPゴムと環化物のブレンド割合は第１表に示
す通りである。
The present invention provides ethylene-propylene rubber with a high cyclization rate.
Regarding a rubber composition blended with 50% or more of a diene polymer cyclized product, the objective is to obtain a rubber composition that has good processability and whose vulcanizate has a high elastic modulus. . Recently, compared to the commonly used vulcanized rubber,
Vulcanized rubber with a higher modulus (1.5 to 2 times or more of the conventional 100% modulus) has become desirable in specific fields. Of course, in this case, it is desirable that the physical properties of the rubber other than the modulus be maintained at the same level as conventional vulcanized rubber, and that the processability is also good. Generally, methods for obtaining a rubber composition with a high elastic modulus include increasing the amount of carbon black added to the rubber or increasing the crosslinking density by increasing the amount of sulfur. It has been difficult to obtain a desirable rubber composition due to problems such as the workability of production and the physical properties and processability of the obtained vulcanized rubber composition. Additionally, a method is known in which a resin is blended with rubber to increase the modulus, but this method poses a problem in processability. The present inventors conducted various studies in an attempt to obtain a rubber composition that has excellent processability, does not deteriorate vulcanized physical properties, and has a high modulus of elasticity.
By blending a propylene rubber and a diene polymer having a cyclization rate of 50% or more, the present invention was completed by completely unexpectedly obtaining results that satisfied the above objectives. Conventionally, it has been known to blend cyclized natural rubber with natural rubber, but the modulus value of this mixture was not sufficient. In order to obtain a high modulus value in this blend, increasing the blended amount of cyclized natural rubber will achieve the objective, but as the amount is increased, the tensile strength will decrease significantly, resulting in a result that is far beyond the intention of the present invention. It is becoming. That is, the present invention uses ethylene-propylene rubber 100
Diene polymer cyclized product with weight part and cyclization rate of 50% or more
It is a rubber composition consisting of 10 to 80 parts by weight. The present invention will be explained in detail below. The ethylene-propylene rubber (hereinafter referred to as EP rubber) used in the present invention is a rubber-like polymer containing a binary copolymer of ethylene and propylene, or a multi-component copolymer of ethylene-propylene and an unsaturated component. It is. The ethylene content in the rubber is 40-80% by weight, the propylene content is 60-20% by weight, and the unsaturated component content is 0-20% by weight. As the unsaturated component, ethylidene norbornene, dicyclopentadiene, 1,4-hexadiene, cyclooctadiene, etc. are used. In addition, diene polymer cyclized products include natural rubber, polyisoprene, polybutadiene,
It is obtained by acting a known cationic catalyst on a diene polymer such as SBR. It is usually obtained by adding a cationic agent as a catalyst to a diene rubber solution or aqueous dispersion. The cyclization rate of the diene polymer cyclized product is 50% or more, preferably 60% or more. The cyclization rate of the diene polymer cyclized product must be 50% or more, which means that when blended with EP rubber,
The objective of the present invention is to obtain a rubber having a high elastic modulus, and a cyclization rate lower than this cannot achieve the objective. Blending of EP rubber and diene polymer cyclized product can be done in solution or emulsion, roll or Banbury mixer. When blended in solution, polymer recovery methods include steam stripping method and non-solvent co-precipitation. method, direct desolvation method, etc. are used. In the case of a milky lotion, a method of coagulating a diene polymer emulsion can usually be used. The blend ratio is 100 parts by weight of EP rubber.
10 to 80 parts by weight of diene polymer cyclized product, preferably
15 to 60 parts by weight. If it is less than 10 parts by weight, the modulus value will not be sufficiently high, and if it is more than 80 parts by weight, the physical properties of the vulcanizate, such as bending resistance and skid resistance, will deteriorate. A sufficiently high modulus value can be obtained even if a diene polymer cyclized product is blended with a material other than EP rubber, such as cis-1,4-polybutadiene rubber (BR) or cis-1,4-polyisoprene rubber (IR). I can't. In addition, the purpose of the present invention can be achieved even if the cyclized product is not a diene polymer such as IR, BR, NR (natural rubber), SBR, etc., as described in detail in the Examples, even if blended with the EP rubber. Not done. Moreover, the cyclization rate of these diene polymer cyclized products must be 50% or more as mentioned above. In the present invention, known additives that are commonly blended into rubber are added to the EP rubber-diene polymer cyclized product blend. As additives, vulcanizing agents, vulcanizing aids, pigments, fillers, softeners, anti-aging agents, dispersants, etc. are used. The rubber composition of the present invention has a compounded rubber Mooney viscosity of
100 or less, and has good processability, and 100% modulus of vulcanizates is usually 60 to 200 Kg/cm 2 and tensile strength.
Over 150Kg/cm 2 and over 100% elongation can be obtained.
Therefore, it is useful for parts that require particularly high elastic modulus, such as tires, anti-vibration rubber, bumpers, belts, flexible joints, guide rollers, fenders, hoses, packing materials, sealing materials, etc. Next, the present invention will be explained in more detail with reference to Examples and Comparative Examples. Example of cyclized product production () IR cyclized product production method Isoprene rubber (JSR IR manufactured by Japan Synthetic Rubber Co., Ltd.)
2200) Dissolve 100g in toluene 3,
BF 3 AcOH in ethylene dichloride solution (1M/
) and reacted at 60°C for 3 hours, then poured into a large amount of methanol containing a small amount of anti-aging agent to solidify. The coagulated product was vacuum dried at 50°C overnight. The cyclization rate was 88%. (Cyclization rate) () BR cyclized product manufacturing method Butadiene rubber (JSR BR manufactured by Japan Synthetic Rubber Co., Ltd.
01) Dissolve 100g in xylene 13, add 20ml of benzyl chloride xylene solution (1M/) and 30ml of AlEtCl 2 xylene solution (1M/), react at 44℃ for 30 minutes, and then add a small amount of anti-aging agent. It was poured into a large amount of methanol and coagulated. The coagulated product was vacuum dried at 50°C overnight. The cyclization rate was 80% (cyclization rate) () Method for producing natural rubber cyclized product A commercially available NR cyclized product (Thermolite P manufactured by Seiko Kagaku Co., Ltd., cyclization rate of 70%) was used. (Cyclized product) Examples 1 to 4, Comparative Examples 1 to 3 JSR EP・33 manufactured by Japan Synthetic Rubber Co., Ltd. as EP rubber
(Contains ethylidene norbornel as an unsaturated component, Mooney value 45, ethylene/propylene = 57/
43, iodine value 26), dissolve the specified amount and the amount of cyclized product listed in Table 1 in about 20 times the amount of toluene, stir well and mix, then pour into a large amount of methanol containing a small amount of anti-aging agent to solidify. and vacuum dried at 50°C overnight. The blend ratio of EP rubber and cyclized product is shown in Table 1.
【表】
上記各例のゴム組成物に第２表に添加物を配合
し内部混練後ロールで混練した後、145℃で30分
プレス加硫した。[Table] Additives shown in Table 2 were blended into the rubber compositions of the above examples, kneaded internally, kneaded with a roll, and then press-vulcanized at 145°C for 30 minutes.
【表】
各例の加硫ゴムの加工性及び物性は第３表の如
くであつた。[Table] The processability and physical properties of the vulcanized rubber of each example were as shown in Table 3.
【表】【table】
【表】
第３表に結果から本発明のゴム組成物は加工性
が優れており、加硫後の弾性率も良好で100％モ
ジユラスはいずれも60Kg/cm2以上の値を示してい
るのに対し比較例のジエン系重合体環化物を含ま
ないときは比較例１では本発明ゴム組成物と同じ
添加剤配合処方では弾性率は低く、弾性率を高め
んとしてカーボンブラツクや硫黄の配合量を大に
した比較例２の如く加工性が悪くなり、またEP
系ゴム以外の例えばIRにジエン系重合体環化物
をブレンドした比較例３では弾性率はさほど大き
くならず、目的を達成できないことが明らかであ
る。[Table] From the results shown in Table 3, the rubber composition of the present invention has excellent processability, and the elastic modulus after vulcanization is also good, with 100% modulus of 60 kg/cm 2 or more. On the other hand, in Comparative Example 1, when the diene polymer cyclized product was not included, the elastic modulus was low with the same additive formulation as the rubber composition of the present invention, and in order to increase the elastic modulus, the amount of carbon black and sulfur was added. As in Comparative Example 2 where the
In Comparative Example 3, in which a cyclized diene polymer was blended with a material other than rubber, for example, IR, the elastic modulus was not so large, and it is clear that the objective could not be achieved.
Claims (1)
上のジエン系重合体環化物とから成るゴム組成
物。 ２ エチレン−プロピレン系ゴムが100重量部、
環化率50％以上のジエン系重合体環化物が10〜80
重量部である特許請求範囲第１項記載のゴム組成
物。[Scope of Claims] 1. A rubber composition comprising an ethylene-propylene rubber and a cyclized diene polymer having a cyclization rate of 50% or more. 2 100 parts by weight of ethylene-propylene rubber,
10 to 80 diene polymer cyclized products with a cyclization rate of 50% or more
The rubber composition according to claim 1, which is in parts by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5552578A JPS54148045A (en) | 1978-05-12 | 1978-05-12 | High modulus rubber composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5552578A JPS54148045A (en) | 1978-05-12 | 1978-05-12 | High modulus rubber composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54148045A JPS54148045A (en) | 1979-11-19 |
| JPS6136536B2 true JPS6136536B2 (en) | 1986-08-19 |
Family
ID=13001123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5552578A Granted JPS54148045A (en) | 1978-05-12 | 1978-05-12 | High modulus rubber composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54148045A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6262178B1 (en) * | 1999-12-28 | 2001-07-17 | The Goodyear Tire & Rubber Company | Rubber blend containing cyclized polyisoprene |
-
1978
- 1978-05-12 JP JP5552578A patent/JPS54148045A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54148045A (en) | 1979-11-19 |
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