JPS63205336A - Rubber composition - Google Patents
Rubber compositionInfo
- Publication number
- JPS63205336A JPS63205336A JP3578087A JP3578087A JPS63205336A JP S63205336 A JPS63205336 A JP S63205336A JP 3578087 A JP3578087 A JP 3578087A JP 3578087 A JP3578087 A JP 3578087A JP S63205336 A JPS63205336 A JP S63205336A
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- polyisoprene rubber
- resistance
- rubber composition
- compound
- 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 57
- 239000005060 rubber Substances 0.000 title claims abstract description 57
- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 229920001195 polyisoprene Polymers 0.000 claims abstract description 25
- -1 benzophenone compound Chemical class 0.000 claims abstract description 12
- 239000012965 benzophenone Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 229920003244 diene elastomer Polymers 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 239000012948 isocyanate Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 150000002513 isocyanates Chemical class 0.000 claims 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000005299 abrasion Methods 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 6
- 239000000446 fuel Substances 0.000 abstract description 4
- 238000005096 rolling process Methods 0.000 abstract description 4
- 230000002265 prevention Effects 0.000 abstract 1
- 229920002857 polybutadiene Polymers 0.000 description 6
- 229920003048 styrene butadiene rubber Polymers 0.000 description 6
- 244000043261 Hevea brasiliensis Species 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000020169 heat generation Effects 0.000 description 5
- 229920003052 natural elastomer Polymers 0.000 description 5
- 229920001194 natural rubber Polymers 0.000 description 5
- 150000008366 benzophenones Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920003051 synthetic elastomer Polymers 0.000 description 4
- 239000002174 Styrene-butadiene Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- WCNOATOQNSHEFK-UHFFFAOYSA-N (3,4-dimethoxyphenyl)-phenylmethanone Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)C1=CC=CC=C1 WCNOATOQNSHEFK-UHFFFAOYSA-N 0.000 description 1
- IHMWJDNMIIEDDN-UHFFFAOYSA-N (4-methoxyphenyl)-(4-methylphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(C)C=C1 IHMWJDNMIIEDDN-UHFFFAOYSA-N 0.000 description 1
- TUMNHQRORINJKE-UHFFFAOYSA-N 1,1-diethylurea Chemical compound CCN(CC)C(N)=O TUMNHQRORINJKE-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 1
- CYMRPDYINXWJFU-UHFFFAOYSA-N 2-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC=C1C(O)=O CYMRPDYINXWJFU-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
- BEUGBYXJXMVRFO-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1 BEUGBYXJXMVRFO-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- ZWPWLKXZYNXATK-UHFFFAOYSA-N bis(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(C)C=C1 ZWPWLKXZYNXATK-UHFFFAOYSA-N 0.000 description 1
- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000007973 cyanuric acids Chemical class 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920003245 polyoctenamer Polymers 0.000 description 1
- 229920003246 polypentenamer Polymers 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- XDDVRYDDMGRFAZ-UHFFFAOYSA-N thiobenzophenone Chemical compound C=1C=CC=CC=1C(=S)C1=CC=CC=C1 XDDVRYDDMGRFAZ-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（発明の技術分野〕
本発明は、耐摩耗性、耐カット性を損なうことなく、反
発弾性を高め、かつ、発熱性を改良したゴム組成物に関
する。DETAILED DESCRIPTION OF THE INVENTION (Technical Field of the Invention) The present invention relates to a rubber composition that has enhanced impact resilience and improved heat generation properties without impairing abrasion resistance and cut resistance.
従来、大型トランク・バス用タイヤには、耐摩耗性、耐
カット・チッピング性が非常に強く要求され、乗用車タ
イヤの場合と異なり、低発熱性は余り重要なタイヤ特性
ではなかった。即ち、転勤抵抗性とスキッド特性は余り
重要ではなかった。Conventionally, tires for large trunks and buses have been required to have very strong wear resistance, cut and chipping resistance, and unlike passenger car tires, low heat build-up has not been a very important tire characteristic. That is, transfer resistance and skid characteristics were not very important.
ところが、道路舗装率の向上、高速道路の普及、更には
ガソリン価格の高騰または社会的省エネルギー指向とが
相俟って、大型タイヤにおいても乗用車タイヤの場合と
同様に耐摩耗性、耐カット・チッピング性以外に経済性
の面から転勤抵抗性が、安全性の面から耐スキツド性と
高速耐久性とが非常に重要なタイヤ特性となってきた。However, due to improvements in road paving rates, the spread of expressways, a sharp increase in gasoline prices, and social trends toward energy conservation, large tires have become less resistant to wear, cut, and chipping than passenger car tires. In addition to performance, transfer resistance has become an extremely important tire characteristic from an economic standpoint, and skid resistance and high-speed durability have become extremely important from a safety standpoint.
即ち、社会の要請として、大型タイヤに関してもスキッ
ド特性を従来レベルに維持した上に転勤抵抗性を低めた
タイヤが要求されるに至った。一般に、転勤抵抗を下げ
るとうエツトスキッド抵抗も低下してしまい、この両特
性は相反する特性で二律背反の関係にあった。しかし、
高ビニルタイプの溶液重合スチレン−ブタジェン共重合
体ゴム（以下、ＳＢＲと略す）を使用すると、この二律
背反の関係を破ることができることが発見され（ＵＳ
ｐａｔｅｎｔ ４，３３４，５６７、特公昭６０−３０
５６２号、特公昭６０−３０５６３号）、乗用車用低燃
費タイヤには、この高ビニルタイプの溶液重合ＳＢＲの
使用が一般化しつつある。That is, society has come to demand tires that maintain skid characteristics at the conventional level and have reduced transfer resistance even for large tires. Generally, lowering the transfer resistance also lowers the tunnel skid resistance, and these two characteristics are contradictory and have an antinomic relationship. but,
It was discovered that this antinomic relationship could be broken by using a high-vinyl type solution-polymerized styrene-butadiene copolymer rubber (hereinafter abbreviated as SBR) (US
Patent 4,334,567, Special Publication 1986-30
562, Japanese Patent Publication No. 60-30563), the use of this high-vinyl type solution polymerized SBR is becoming common in fuel-efficient tires for passenger cars.
しかしながら、大型トラック・バス用タイヤの場合、タ
イヤにかかるシビアリテイーが著しく高いため前記の高
ビニルタイプの溶液重合ＳＢＲを使用すると、耐摩耗性
が著しく悪化し、実用に供することができないのが現状
である。However, in the case of tires for large trucks and buses, the severity of the tires is extremely high, so if the above-mentioned high vinyl type solution polymerized SBR is used, the abrasion resistance will deteriorate significantly and it is currently impossible to put it into practical use. be.
したがって、大型タイヤの低燃費タイヤトレッド用ゴム
組成物には天然ゴムが主体に使用され、転勤抵抗を更に
改良するためには、ポリブタジェンゴムをブレンドする
のが一般的である。Therefore, natural rubber is mainly used in rubber compositions for fuel-efficient tire treads for large tires, and in order to further improve transfer resistance, it is common to blend polybutadiene rubber into the composition.
しかし、このポリブタジェンゴムをブレンドすると著し
く耐カット性と耐チッピング性、スキッド特性が悪化し
てしまうことから限界がある。However, there is a limit to this because blending this polybutadiene rubber significantly deteriorates cut resistance, chipping resistance, and skid characteristics.
そこで、タイヤ構造面で改良する方法が一般化している
。即ち、トレッドをキャンプトレッドとベーストレッド
の二層構造とし、キャップトレッドゴムには耐摩耗性、
耐カット性、耐ウエツトスキツド性等の優れたゴムを配
し、ベーストレッド用ゴムには発熱性の低い、低ヒステ
リシスロスのゴムを配することで、トレッド部全体とし
ては他特性を余り低下させずに転勤抵抗性を改良する技
術もある。しかし、この二層トレッド構造にも大きな欠
点がある。即ち、トレンド全体のヒステリシスロスを下
げるためにはベーストレッド部の体積を太き（とる必要
があり、そうすると摩耗終期にベーストレンド部が露出
するため摩耗終期の耐摩耗性及び耐カット性が著しく低
下してしまう。ときには、ベルト部を損傷してしまうた
め、更生性も低下してしまう。また、摩耗終期の耐摩耗
性を考慮してベーストレンド部の体積を小さくすると、
転勤抵抗性の改善効果は少なくなってしまう。したがっ
て、トレンド用ゴムとして、天然ゴムなみの耐カット性
、耐摩耗性を有し、かつ、大幅に発熱の低いゴム材料が
強く要求されていた。特開昭５９−１１７５４８号によ
れば、合成ポリイソプレンゴムが上記条件を満足するこ
とが記載されているが、これとても満足できるものでは
ない。Therefore, methods of improving the tire structure have become common. In other words, the tread has a two-layer structure of camp tread and base tread, and the cap tread rubber has wear resistance and
By using rubber with excellent cut resistance and wet skidding resistance, and by using rubber with low heat generation and low hysteresis loss for the base tread, the tread as a whole does not significantly deteriorate other properties. There are also techniques to improve transfer resistance. However, this two-layer tread structure also has major drawbacks. In other words, in order to reduce the hysteresis loss of the entire trend, it is necessary to increase the volume of the base tread part, which exposes the base trend part at the end of wear, significantly reducing the wear resistance and cut resistance at the end of wear. In some cases, the belt part is damaged and the retreadability is also reduced.In addition, if the volume of the base trend part is made smaller in consideration of wear resistance at the end of wear,
The effect of improving transfer resistance will be reduced. Therefore, there has been a strong demand for a rubber material that has cut resistance and abrasion resistance comparable to natural rubber and generates significantly less heat as a trendy rubber. JP-A-59-117548 describes that synthetic polyisoprene rubber satisfies the above conditions, but this is not very satisfactory.
本発明は、耐摩耗性、耐カット性、耐ウエツトスキツド
性を維持しつつ、反発弾性が著しく高く、かつ発熱性が
著しく改良されたゴム組成物を提供することを目的とす
る。このゴム組成物は、特に高速用の大型タイヤのゴム
材料として好適に利用される。An object of the present invention is to provide a rubber composition that has significantly high impact resilience and significantly improved heat generation properties while maintaining abrasion resistance, cut resistance, and wet skid resistance. This rubber composition is particularly suitable for use as a rubber material for large tires for high speed use.
このため、本発明は、アルカリ金属付加ポリイソプレン
ゴム又はアルカリ土類金属付加ポリイソプレンゴムに、
ベンゾフェノン系化合物、分子中に−ＣＮ＜結合を有す
る化合物（ＭはＩ
Ｏ又はＳ）、又はイソシアナート系化合物を反応せしめ
た変性ポリイソプレンゴム２０〜１００重量部と他のジ
エン系ゴム０〜８０重量部とからなることを特徴とする
ゴム組成物を要旨とするものである。Therefore, the present invention provides alkali metal-added polyisoprene rubber or alkaline earth metal-added polyisoprene rubber,
20 to 100 parts by weight of a modified polyisoprene rubber reacted with a benzophenone compound, a compound having a -CN< bond in the molecule (M is IO or S), or an isocyanate compound, and 0 to 80 parts by weight of another diene rubber. The gist of the invention is a rubber composition characterized in that it consists of parts by weight.
以下、本発明の構成につき詳しく説明する。Hereinafter, the configuration of the present invention will be explained in detail.
本発明で用いる変性ポリイソプレンゴムは、アルカリ金
属付加ポリイソプレンゴム又はアルカリ土類金属付加ポ
リイソプレンゴムに、ベンゾフェノン系化合物、分子中
に−ＣＮ＜結合を有する化合物（Ｍは０又はＳ）、又は
イソシアナート系化合物を反応せしめたものである。The modified polyisoprene rubber used in the present invention is alkali metal-added polyisoprene rubber or alkaline earth metal-added polyisoprene rubber, and a benzophenone compound, a compound having a -CN< bond in the molecule (M is 0 or S), or It is made by reacting isocyanate compounds.
この変性ポリイソプレンは、イソプレンを溶液重合に際
して通常使用されるアルカリ金属基材触媒又はアルカリ
土類金属触媒を用いて重合させ、その分子鎖の末端にア
ルカリ金属またはアルカリ土類金属が結合しているポリ
イソプレンゴムと、ベンゾフェノン類又はチオベンゾフ
ェノン類とを反応させて得られるポリイソプレンゴムで
あって、分子鎖末端に炭素−炭素結合で下記一般式で示
される原子団が導入されたものである。This modified polyisoprene is produced by polymerizing isoprene using an alkali metal-based catalyst or alkaline earth metal catalyst commonly used in solution polymerization, and an alkali metal or alkaline earth metal is bonded to the end of the molecular chain. It is a polyisoprene rubber obtained by reacting polyisoprene rubber with benzophenones or thiobenzophenones, and has an atomic group represented by the following general formula introduced at the end of the molecular chain via a carbon-carbon bond.
（式中Ｒ８及びＲ２は水素又は置換基を、ＭはＯ又はＳ
を、ｍ及びｎは整数をそれぞれ示す）ここで使用される
ベンゾフェノン類及びチオベンゾフェノン類は、例えば
、４，４′−ビス（ジメチルアミノ）−ベンゾフェノン
、４１４′−ビス（ジエチルアミノ）−ベンゾフェノン
、４．４＝ビス （ジブチルアミノ）−ベンゾフェノン
、４゜４′−ジアミノベンゾフェノン、４−ジメチルア
ミノベンゾフェノン等及びこれらの対応のチオベンゾフ
ェノンである。これらのうちで一方あるいは両方のベン
ゼン環に少なくとも１つのアミノ基、アルキルアミノ基
あるいはジアルキルアミノ基を有するベンゾフェノン及
びチオベンゾフェノンが特に好ましい。前記のアミノ基
以外にもアルコキシ基、ハロゲンあるいは炭化水素残基
を置換基として少なくとも１つ有するベンゾフェノン類
及びチオベンゾフェノン類、例えば、４，４′−ジェト
キシベンゾフェノン、３．４−ジメトキシベンゾフェノ
ン、４，４′−ジメチルベンゾフェノン、３，３′−ジ
シクロベンゾフェノン、４−メチル−４′−メトキシベ
ンゾフェノン、２．２’、３．３’−テトラメチルベン
ゾフェノン、２．２′−シクロベンゾフェノンなど及び
対応のチオベンゾフェノンが、また置換基のないベンゾ
フェノン及びチオベンゾフェノンも使用することができ
る。(In the formula, R8 and R2 are hydrogen or a substituent, M is O or S
, m and n each represent an integer) The benzophenones and thiobenzophenones used here are, for example, 4,4'-bis(dimethylamino)-benzophenone, 414'-bis(diethylamino)-benzophenone, 4 .4=bis(dibutylamino)-benzophenone, 4°4'-diaminobenzophenone, 4-dimethylaminobenzophenone, etc., and their corresponding thiobenzophenones. Among these, benzophenone and thiobenzophenone having at least one amino group, alkylamino group or dialkylamino group on one or both benzene rings are particularly preferred. Benzophenones and thiobenzophenones having at least one alkoxy group, halogen or hydrocarbon residue as a substituent in addition to the above amino group, such as 4,4'-jethoxybenzophenone, 3,4-dimethoxybenzophenone, 4 , 4'-dimethylbenzophenone, 3,3'-dicyclobenzophenone, 4-methyl-4'-methoxybenzophenone, 2.2', 3.3'-tetramethylbenzophenone, 2.2'-cyclobenzophenone, etc. and corresponding ones. thiobenzophenones, but also unsubstituted benzophenones and thiobenzophenones can be used.
また、分子鎖末端に、分子中に−Ｃ−＞＜結合（但し、
式中のＭはＯ原子又はＳ原子を表わす）を有する化合物
を導入する。この化合物としては、ホルムアミド、アセ
トアミド、アミノアセトアミド、ＮＩ Ｎ′−ジメチル
アミノアセトアミド、アクリルアミド、ニコチンアミド
、フタル酸アミド、オキサミド、２−フランカルボン酸
アミド、キノリン−２−カルボン酸アミドなどのアミド
化合物、コハク酸イミド、マレイミド、Ｎ−メチルマレ
イミド、フタルイミドなどのイミド化合物、ε−カプロ
ラクタム、Ｎ〜メチル−ε−カプロラクタム、２−ピロ
リドン、２−ピペリドン、Ｎ−メチル−２−ピロリドン
、Ｎ−メチル−２−ピペリドン、２−キノリンなどのラ
クタム化合物、尿素、Ｎ、 Ｎ′−ジメチル尿素、Ｎ、
Ｎ仁ジエチル尿素、Ｎ、Ｎ仁ジメチル−Ｎ’、Ｎ′−
ジフェニル尿素などの尿素化合物、カルバミン酸メチル
、イソシアヌル酸などのイソシアヌル酸誘導体である。In addition, -C->< bond (however,
(M in the formula represents an O atom or an S atom) is introduced. These compounds include amide compounds such as formamide, acetamide, aminoacetamide, NI N'-dimethylaminoacetamide, acrylamide, nicotinamide, phthalic acid amide, oxamide, 2-furancarboxylic acid amide, and quinoline-2-carboxylic acid amide; Imide compounds such as succinimide, maleimide, N-methylmaleimide, phthalimide, ε-caprolactam, N~methyl-ε-caprolactam, 2-pyrrolidone, 2-piperidone, N-methyl-2-pyrrolidone, N-methyl-2 -lactam compounds such as piperidone, 2-quinoline, urea, N, N'-dimethylurea, N,
N-diethyl urea, N, N-dimethyl-N', N'-
These are urea compounds such as diphenyl urea, and isocyanuric acid derivatives such as methyl carbamate and isocyanuric acid.
イソシアナート系化合物としては、例えば２゜４−トリ
レンジイソシアナート、ジフェニルメタンジイソシアナ
ート、ナフタレンジイソシアナート、ヘキサメチレンジ
イソシアナート等である。Examples of the isocyanate compounds include 2°4-tolylene diisocyanate, diphenylmethane diisocyanate, naphthalene diisocyanate, and hexamethylene diisocyanate.
この変性ポリイソプレンゴムとブレンドするための他の
ジエン系ゴムとしては、天然ゴム、合成ポリイソプレン
ゴム、スチレン−ブタジェン共重合ゴム、ポリブタジェ
ンゴム、ポリクロロプレンゴム、ポリペンテナマー、ポ
リオクテナマー、ブタジェン−イソプレン共重合コム、
スチレン−イソプレン共重合ゴムなど、何れか一つでも
良く、また二種類以上であってもよい。Other diene rubbers to be blended with this modified polyisoprene rubber include natural rubber, synthetic polyisoprene rubber, styrene-butadiene copolymer rubber, polybutadiene rubber, polychloroprene rubber, polypentenamer, polyoctenamer, butadiene-isoprene rubber, etc. polymerized comb,
Any one of styrene-isoprene copolymer rubber or the like may be used, or two or more types may be used.
中でも、天然ゴム、合成ポリイソプレンゴム、スチレン
−ブタジェン共重合ゴム、ポリブタジエンゴムが特に好
ましい。Among these, natural rubber, synthetic polyisoprene rubber, styrene-butadiene copolymer rubber, and polybutadiene rubber are particularly preferred.
変性ポリイソプレンゴムと他のジエン系ゴムとのブレン
ド比は、変性ポリイソプレンゴム単独使用が最も効果が
大きく、少なくとも変性ボＩＪ イ’／ ７”レンゴム
を２０重量部以上ブレンドする必要がある。２０重量部
より少ないと発熱性を低減する度合が少なく、タイヤに
用いた場合、タイヤの転勤抵抗性、即ち、燃費性は改善
されない。本発明のゴム組成物は、上記ポリマー以外に
、通常ゴム工業で使用されるカーボンブランク等の補強
剤、充填剤、老化防止剤、加硫剤、加硫助剤、加硫促進
剤、プロセス油等を適宜配合しても構わない。Regarding the blend ratio of modified polyisoprene rubber and other diene rubber, using modified polyisoprene rubber alone has the greatest effect, and it is necessary to blend at least 20 parts by weight of modified polyisoprene rubber.20 If the amount is less than 1 part by weight, the degree to which heat generation is reduced is small, and when used in tires, the transfer resistance, that is, the fuel efficiency of the tires will not be improved. A reinforcing agent such as a carbon blank used in the above, a filler, an anti-aging agent, a vulcanizing agent, a vulcanizing aid, a vulcanizing accelerator, a process oil, etc. may be appropriately blended.
以下に実施例および比較例を示す。Examples and comparative examples are shown below.
実施例、比較例
下記第２表の配合１１ｋ１１〜５の配合処方（重量部）
に従ってゴム組成物を作製し、トレ・７ドコンバウンド
のみをこの５種のゴム組成物に変更した５種類の１００
０Ｒ２０１４ＰＲのラジアルタイヤを試作し、タイヤ特
性、即ち、転動抵抗、ウェソＯ
トスキッド抵抗、高速耐久性、実車耐摩耗性を測定した
。この結果を第３表に示す。Examples and Comparative Examples The formulations of formulations 11k11 to 5 in Table 2 below (parts by weight)
5 types of 100 rubber compositions were prepared according to the above, and only the TR-7 compound was changed to these 5 types of rubber compositions.
A prototype 0R2014PR radial tire was manufactured, and the tire properties, ie, rolling resistance, weso O toss skid resistance, high-speed durability, and actual vehicle wear resistance were measured. The results are shown in Table 3.
また、タイヤ試作に供したゴム組成物を１５０℃×３０
分間プレス加硫し、その加硫物物性を測定した。この結
果を第２表に示す。In addition, the rubber composition used for tire trial production was heated to 30°C at 150°C.
Press vulcanization was performed for a minute, and the physical properties of the vulcanized product were measured. The results are shown in Table 2.
各試験の評価方法は以下の通りである。The evaluation method for each test is as follows.
〈引張り特性〉： ＪＩＳ Ｋ ６３０１に準拠。<Tensile properties>: Compliant with JIS K 6301.
く反発弾性〉： ＪＩＳ Ｋ ６３０１に準拠。Resilience〉: Compliant with JIS K 6301.
＜ｔａｎδ〉：
若木製作所製の粘弾性スペクトロメーターを用い、伸長
変形で歪率が１０±２％、振動数２０Ｈｚの条件下で測
定した。<tan δ>: Measured using a viscoelastic spectrometer manufactured by Wakagi Seisakusho under the conditions of elongation deformation with a strain rate of 10±2% and a frequency of 20 Hz.
〈転動抵抗〉：
米国自動車技術協会報文ＳＡＥ第７７０８７５号に記載
の方法に準じて測定した。数値が低い程、転勤抵抗が小
さく、燃費性が良い。<Rolling resistance>: Measured according to the method described in American Society of Automotive Engineers Bulletin SAE No. 770875. The lower the value, the lower the transfer resistance and the better the fuel efficiency.
〈実車耐摩耗性指数〉：
平ボデー１０トントランクの総輪にテストタイヤを装着
し、−船路を６万ｋｍ走行後の残溝を測定し、Ｉｎ当り
の走行ｉを求め、タイヤ階１のタイヤを１００として指
数表示した。従って、指数が大きいほど、耐摩耗性は良
好である。<Actual vehicle wear resistance index>: A test tire was attached to all wheels of a 10-ton trunk with a flat body, and the remaining tread was measured after traveling 60,000 km on a ship route, and the travel i per In was calculated. The tires are expressed as an index with 100 as the number of tires. Therefore, the larger the index, the better the wear resistance.
くウェットスキッド抵抗〉：
濡れたアスファルト路面において、実車により速度４Ｑ
ｋｍ／ｈｒ、７Ｑｋｍ／ｈｒの各速度で急制動を加え、
完全に制止するまでの走行距離を測定し、以下の式で指
数化した。Wet skid resistance: On a wet asphalt road, the speed of 4Q is measured by an actual vehicle.
Apply sudden braking at each speed of km/hr, 7Qkm/hr,
The distance traveled until the vehicle came to a complete stop was measured and converted into an index using the following formula.
＊ ４０ｋｍ／ｈと７０ｋｍ／ｈの制動距離の和く高速
耐久性〉：
室内ドラム試験において、下記第１表に示す時間ステッ
プで荷重を累積し、５５ｋｍ／ｈの一定速度で走行させ
、どのステップで故障に至るかの所謂ＦＭＶＳＳ Ｎａ
１１９条件に従う室内耐久試験を実施し、比較例１の走
行距離を１００として指数表示した。従って、指数が大
きい程耐久性は優れる。* High-speed durability based on the sum of braking distances of 40 km/h and 70 km/h>: In an indoor drum test, the load was accumulated at the time steps shown in Table 1 below, the vehicle was run at a constant speed of 55 km/h, and at which step The so-called FMVSS Na that may lead to failure
An indoor durability test was conducted under 119 conditions, and the mileage of Comparative Example 1 was set as 100 and expressed as an index. Therefore, the larger the index, the better the durability.
（来夏以下余白） 第 ２ 表 本２ 日本ゼオン製Ｎ１ｐｏｌ Ｉに２（イ）。(Left below next summer) Table 2 Book 2 Nippon Zeon N1pol I to 2 (A).
＊３ 日本ゼオン製Ｎ１ｐｏｌ １２００゜＊４Ｎ−オ
キシジエチレンベンゾチアジルスルフェンアミド。*3 N1pol 1200° manufactured by Nippon Zeon *4 N-oxydiethylenebenzothiazylsulfenamide.
本発明のタイヤ用、ここではトレッド用ゴム組成物は、
比較例のゴム組成物と比較すれば、明らかに反発弾性が
高く、ｔａｎδが小さい。即ち、ヒステリシスロスが小
さい。また、破壊特性もほとんど変わらない。ポリブタ
ジェンゴムを２０重量部ブレンドした配合隘５でも同様
な効果が発現される。The rubber composition for tires, here for treads, of the present invention includes:
When compared with the rubber composition of the comparative example, the impact resilience is clearly high and the tan δ is small. That is, hysteresis loss is small. Furthermore, the fracture characteristics are almost unchanged. A similar effect is obtained with blending number 5 in which 20 parts by weight of polybutadiene rubber is blended.
実施例２の結果より、タイヤ１ＩｋＬ３の本発明のタイ
ヤは、転勤抵抗指数が低く、燃費性の良いことを示して
いる。また、高速耐久性も大幅に改良されている。一方
、ウェットスキッド抵抗と実車の耐摩耗性に関しても、
天然ゴム及び合成ポリイソプレンゴムより悪くなること
はない。The results of Example 2 show that the tire of the present invention (tire 1IkL3) has a low transfer resistance index and good fuel efficiency. In addition, high-speed durability has also been significantly improved. On the other hand, regarding wet skid resistance and actual vehicle wear resistance,
It is no worse than natural rubber and synthetic polyisoprene rubber.
ポリブタジェンゴムをブレンドしたタイヤ阻５は、転動
抵抗指数が低く、かつ高速耐久性も改良されている上に
、ウェットスキッド抵抗は同等で、耐摩耗性も改良され
る。以上の如く、本発明の変性ポリイソプレンゴムを用
いたゴム組成物は、大型タイヤの耐久性向上及び転勤抵
抗性の低減に著しい効果を示す。The tire barrier 5 blended with polybutadiene rubber has a low rolling resistance index and improved high-speed durability, has the same wet skid resistance, and has improved wear resistance. As described above, the rubber composition using the modified polyisoprene rubber of the present invention shows remarkable effects in improving the durability of large tires and reducing transfer resistance.
以上説明したように本発明によれば、耐摩耗性、耐カッ
ト性、耐ウエツトスキツド性、反発弾性、低発熱性等に
優れたゴム組成物を得ることができる。このゴム組成物
は、タイヤトレンド部、タイヤサイドウオール部、工業
用ベルト、ホース等のゴム質として有用である。As explained above, according to the present invention, a rubber composition excellent in abrasion resistance, cut resistance, wet skid resistance, impact resilience, low heat generation property, etc. can be obtained. This rubber composition is useful as a rubber material for tire trend parts, tire sidewall parts, industrial belts, hoses, and the like.
Claims (1)
金属付加ポリイソプレンゴムに、ベンゾフェノン系化合
物、分子中に▲数式、化学式、表等があります▼結 合を有する化合物（ＭはＯ又はＳ）、又はイソシアナー
ト系化合物を反応せしめた変性ポリイソプレンゴム２０
〜１００重量部と他のジエン系ゴム０〜８０重量部とか
らなることを特徴とするゴム組成物。[Scope of Claims] Alkali metal-added polyisoprene rubber or alkaline earth metal-added polyisoprene rubber contains a benzophenone compound, a compound having a ▲ mathematical formula, chemical formula, table, etc. in the molecule ▼ a bond (M is O or S). ), or modified polyisoprene rubber 20 reacted with an isocyanate compound
1. A rubber composition comprising 100 parts by weight and 0 to 80 parts by weight of another diene rubber.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3578087A JPS63205336A (en) | 1987-02-20 | 1987-02-20 | Rubber composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3578087A JPS63205336A (en) | 1987-02-20 | 1987-02-20 | Rubber composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63205336A true JPS63205336A (en) | 1988-08-24 |
Family
ID=12451412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3578087A Pending JPS63205336A (en) | 1987-02-20 | 1987-02-20 | Rubber composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63205336A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012086496A1 (en) * | 2010-12-24 | 2012-06-28 | 日本ゼオン株式会社 | Conjugated diene rubber, rubber composition, rubber crosslink product, and tire |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58189203A (en) * | 1982-04-30 | 1983-11-04 | Nippon Zeon Co Ltd | Rubber composition |
| JPS6142552A (en) * | 1984-08-02 | 1986-03-01 | Nippon Zeon Co Ltd | Rubber composition |
| JPS61171749A (en) * | 1985-01-25 | 1986-08-02 | Japan Synthetic Rubber Co Ltd | Isoprene rubber composition |
-
1987
- 1987-02-20 JP JP3578087A patent/JPS63205336A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58189203A (en) * | 1982-04-30 | 1983-11-04 | Nippon Zeon Co Ltd | Rubber composition |
| JPS6142552A (en) * | 1984-08-02 | 1986-03-01 | Nippon Zeon Co Ltd | Rubber composition |
| JPS61171749A (en) * | 1985-01-25 | 1986-08-02 | Japan Synthetic Rubber Co Ltd | Isoprene rubber composition |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012086496A1 (en) * | 2010-12-24 | 2012-06-28 | 日本ゼオン株式会社 | Conjugated diene rubber, rubber composition, rubber crosslink product, and tire |
| JPWO2012086496A1 (en) * | 2010-12-24 | 2014-05-22 | 日本ゼオン株式会社 | Conjugated diene rubber, rubber composition, rubber cross-linked product, and tire |
| US8937130B2 (en) | 2010-12-24 | 2015-01-20 | Zeon Corporation | Conjugated diene rubber, rubber composition, cross-linked rubber, and tire |
| JP5831461B2 (en) * | 2010-12-24 | 2015-12-09 | 日本ゼオン株式会社 | Conjugated diene rubber, rubber composition, rubber cross-linked product, and tire |
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