JP2008144044A - Rubber composition for tire - Google Patents
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Abstract
Description
本発明は、タイヤ用ゴム組成物に関し、更に詳しくは、エポキシ樹脂及び窒素含有硬化剤を配合した、ゴム組成物の破断伸びと硬度を共に向上させ、かつ良好な加工性を有するタイヤ用ゴム組成物に関する。 The present invention relates to a rubber composition for tires, and more specifically, a rubber composition for tires that contains both an epoxy resin and a nitrogen-containing curing agent, improves the elongation at break and hardness of the rubber composition, and has good processability. Related to things.
一般的に、ゴムの硬度を上げると破断伸びが低下することが知られており、従来は硬度を上げながら、同時に破断伸びを向上させることは相反する性能を両立させることであり、困難とされてきた。実際に、フェノール樹脂と硬化剤を併用することでゴムを硬くし、補強性を高めることが通常行われているが（例えば特許文献１参照）、ゴムを硬くするほど破断伸びが低下してしまうという欠点がある。 In general, it is known that the elongation at break decreases when the hardness of rubber is increased. Conventionally, it is difficult to improve the elongation at break at the same time while increasing the hardness. I came. Actually, it is usual to harden the rubber by using a phenol resin and a curing agent in combination, and to enhance the reinforcing property (see, for example, Patent Document 1). However, the harder the rubber, the lower the elongation at break. There is a drawback.
従って、本発明の目的はゴムの破断伸びと硬度をともに向上させ、かつ良好な加工性を有するゴム組成物を提供することにある。 Accordingly, an object of the present invention is to provide a rubber composition which improves both the elongation at break and hardness of rubber and has good processability.
本発明に従えば、ジエン系ゴム１００重量部、シリカ５〜１００重量部、軟化点が１００℃以下のグリシジルエーテルタイプのエポキシ樹脂０．５〜２０重量部及び、エポキシ樹脂に対して１〜１０重量％の、分子内に窒素原子を含有する硬化剤を含んでなるタイヤ用ゴム組成物が提供される。 According to the present invention, 100 parts by weight of a diene rubber, 5 to 100 parts by weight of silica, 0.5 to 20 parts by weight of a glycidyl ether type epoxy resin having a softening point of 100 ° C. or less, and 1 to 10 with respect to the epoxy resin There is provided a rubber composition for a tire comprising a curing agent containing a nitrogen atom in a molecule in an amount of% by weight.
本発明によれば、ジエン系ゴム１００重量部に対し、シリカを５〜１００重量部、軟化点１００℃以下のグリシジルエーテルタイプのエポキシ樹脂を０．５〜２０重量部、そして分子内に窒素原子を含有する硬化剤をエポキシ樹脂に対して１〜１０重量％配合することによって、ゴム組成物の破断伸びと硬度とをともに向上させ、かつ良好な加工性を有するゴム組成物を得ることができる。 According to the present invention, 5 to 100 parts by weight of silica, 0.5 to 20 parts by weight of a glycidyl ether type epoxy resin having a softening point of 100 ° C. or less, and nitrogen atoms in the molecule with respect to 100 parts by weight of diene rubber. By blending 1 to 10% by weight of the curing agent containing the epoxy resin, it is possible to improve both the elongation at break and hardness of the rubber composition and to obtain a rubber composition having good processability. .
前述の如く、従来は、一般的にゴムの硬度を上げると破断伸びが低下するので、硬度を上げながら、同時に破断伸びを向上させることは困難とされてきた。然るに、本発明者らは、前記課題を解決すべく研究を進めた結果、特定のエポキシ樹脂と硬化剤を使用することによって、ゴム組成物の破断伸びと硬度をともに向上させ、かつ良好な加工性を有するタイヤ用ゴム組成物を得ることに成功した。 As described above, conventionally, when the hardness of rubber is generally increased, the elongation at break decreases. Therefore, it has been difficult to improve the elongation at break while increasing the hardness. However, as a result of researches to solve the above problems, the present inventors have improved the elongation at break and hardness of the rubber composition by using a specific epoxy resin and a curing agent, and have good processing. The present invention succeeded in obtaining a rubber composition for tires having properties.
本発明において使用するジエン系ゴムは、例えば天然ゴム（ＮＲ）、ポリイソプレンゴム（ＩＲ）、ポリブタジエンゴム（ＢＲ）、スチレン−ブタジエン共重合体ゴム（ＳＢＲ）、クロロプレンゴム（ＣＲ）、ニトリルゴム（ＮＢＲ）、エポキシ化天然ゴム（ＥＮＲ）などを含み、これらは単独又は任意のブレンドとして使用することができる。 Examples of the diene rubber used in the present invention include natural rubber (NR), polyisoprene rubber (IR), polybutadiene rubber (BR), styrene-butadiene copolymer rubber (SBR), chloroprene rubber (CR), nitrile rubber ( NBR), epoxidized natural rubber (ENR), etc., which can be used alone or in any blend.
本発明によれば、前記ジエン系ゴム１００重量部に対し、シリカを５〜１００重量部、好ましくは１０〜９０重量部配合する。シリカの配合量が少ないとゴムの補強性が弱くなるので好ましくなく、逆に多いとゴムが硬くなりすぎ実用的でなくなるので好ましくない。なお、シリカとしては従前からタイヤゴム組成物などに使用されている任意のものとすることができ、各種市販品を利用することができる。 According to the present invention, 5 to 100 parts by weight, preferably 10 to 90 parts by weight of silica is blended with 100 parts by weight of the diene rubber. If the amount of silica is small, it is not preferable because the reinforcing property of the rubber becomes weak. On the other hand, if the amount is too large, the rubber becomes too hard to be practical. In addition, as silica, it can be set as the arbitrary thing conventionally used for the tire rubber composition etc., and various commercial items can be utilized.
本発明のゴム組成物に配合するエポキシ樹脂はジエン系ゴム１００重量部に対し、０．５〜２０重量部、好ましくは１〜２０重量部配合する。この配合量が少ないと架橋成分が少なくなることから物理的特性の向上がはかれないので好ましくなく、逆に多いとゴム中の架橋構造が多くなりすぎることから実用的なゴムが得られないので好ましくない。本発明において使用するエポキシ樹脂は、グリシジルエーテルタイプのエポキシ樹脂であり、軟化点が１００℃以下、好ましくは４５〜１００℃である。エポキシ樹脂がグリシジルエーテルタイプであることにより、エポキシ基が末端にあるため、架橋が進みやすくなる。また、軟化点が１００℃以下のエポキシ樹脂であれば、分子量がそれほど大きくないため、ゴムとの相溶性も良好であるので好ましい。グリシジルエーテルタイプのエポキシ樹脂の具体例をあげれば、例えば下記式（Ｉ）及び（II）のものを例示することができる（式中、Ｒ及びＲ1はそれぞれ独立にアルキル基、好ましくは炭素数１〜１５のアルキル基あるいは水素原子を示し、ｎは平均１〜２０の数である）。かかるエポキシ樹脂は公知のものであり、例えばジャパンエポキシレジン（株）製エピコート１００１，１５７Ｓ７０、東都化成（株）製ＹＤ−０１２，ＹＤＣＮ−７０２などの市販品を用いることができる。なお、その他のエポキシ樹脂として各種ポリフェノール化合物のグリシジルエーテル化物および各種ノボラック樹脂のグリシジルエーテル化物なども使用することができる。 The epoxy resin blended in the rubber composition of the present invention is blended in an amount of 0.5 to 20 parts by weight, preferably 1 to 20 parts by weight based on 100 parts by weight of the diene rubber. If this amount is too small, it is not preferable because physical properties cannot be improved because the crosslinking component is reduced. On the other hand, if the amount is too large, there will be too much crosslinking structure in the rubber, so a practical rubber cannot be obtained. It is not preferable. The epoxy resin used in the present invention is a glycidyl ether type epoxy resin, and has a softening point of 100 ° C. or less, preferably 45 to 100 ° C. Since the epoxy resin is of a glycidyl ether type, the epoxy group is at the end, so that the cross-linking is facilitated. In addition, an epoxy resin having a softening point of 100 ° C. or lower is preferable because the molecular weight is not so large and compatibility with rubber is good. Specific examples of the glycidyl ether type epoxy resin include those of the following formulas (I) and (II) (wherein R and R 1 are each independently an alkyl group, preferably a carbon number) 1 to 15 alkyl groups or hydrogen atoms, and n is an average of 1 to 20). Such epoxy resins are known, and commercially available products such as Epicoat 1001, 157S70 manufactured by Japan Epoxy Resin Co., Ltd., YD-012, YDCN-702 manufactured by Toto Kasei Co., Ltd. can be used. As other epoxy resins, glycidyl etherified products of various polyphenol compounds and glycidyl etherified products of various novolak resins can also be used.
本発明において使用する硬化剤は分子内に窒素原子を有するもので、例えば下記式に示すような環状アミンをあげることができる。かかる環状アミンは公知のものであり、例えば大内新興化学工業（株）製ノクセラーＨ、花王（株）製カオーライザーＮｏ．３０Ｐなどの市販品を用いることができる。なお、その他の窒素含有硬化剤としてはピペラジン誘導体、ピロリジン誘導体などの各種環状アミン化合物をあげることができる。 The curing agent used in the present invention has a nitrogen atom in the molecule, and examples thereof include cyclic amines as shown in the following formula. Such cyclic amines are known, and examples include Noxeller H manufactured by Ouchi Shinsei Chemical Industry Co., Ltd. and Kao Raiser No. manufactured by Kao Corporation. Commercial products such as 30P can be used. Examples of other nitrogen-containing curing agents include various cyclic amine compounds such as piperazine derivatives and pyrrolidine derivatives.
本発明において使用する硬化剤はエポキシ樹脂重量に対し１〜１０重量％、好ましくは２〜１０重量％配合する。この配合量が少ないとエポキシ樹脂が十分に反応しないため、物理的特性の向上がはかれないので好ましくなく、逆に多いと反応に寄与しない余分な硬化剤が多くなることで物理的特性が悪化するので好ましくない。 The hardening | curing agent used in this invention mix | blends 1-10 weight% with respect to the weight of an epoxy resin, Preferably it is 2-10 weight%. If this amount is too small, the epoxy resin will not react sufficiently, and physical properties will not improve, which is not preferable. On the other hand, if the amount is too large, the physical properties will deteriorate due to an increase in excess curing agent that does not contribute to the reaction. This is not preferable.
本発明に係るゴム組成物には、前記した成分に加えて、カーボンブラックなどのその他の補強剤（フィラー）、加硫又は架橋剤、加硫又は架橋促進剤、各種オイル、老化防止剤、可塑剤などのタイヤ用、その他のゴム組成物用に一般的に配合されている各種添加剤を配合することができ、かかる添加剤は一般的な方法で混練して組成物とし、加硫又は架橋するのに使用することができる。これらの添加剤の配合量は本発明の目的に反しない限り、従来の一般的な配合量とすることができる。 In addition to the components described above, the rubber composition according to the present invention includes other reinforcing agents (fillers) such as carbon black, vulcanization or crosslinking agents, vulcanization or crosslinking accelerators, various oils, anti-aging agents, plastics Various additives generally blended for tires such as additives and other rubber compositions can be blended, and these additives are kneaded by a general method to form a composition, which is then vulcanized or crosslinked. Can be used to do. As long as the amount of these additives is not contrary to the object of the present invention, a conventional general amount can be used.
以下、実施例によって本発明を更に説明するが、本発明の範囲をこれらの実施例に限定するものでないことはいうまでもない。 EXAMPLES Hereinafter, although an Example demonstrates this invention further, it cannot be overemphasized that the scope of the present invention is not limited to these Examples.
実施例１〜２及び比較例１〜５
サンプルの調製
表Ｉに示す配合において、硬化剤、加硫促進剤および硫黄を除く成分を１．８リットルの密閉型ミキサーで５分間混練し、１３５℃に達したときに放出してマスターバッチを得た。このマスターバッチに硬化剤、加硫促進剤および硫黄をオープンロールで混練し、ゴム組成物を得た。このゴム組成物を用いて以下に示す試験法で未加硫物性（ムーニー粘度）を評価した。結果は表Ｉに示す。
Examples 1-2 and Comparative Examples 1-5
Sample preparation In the formulation shown in Table I, the components excluding the curing agent, vulcanization accelerator and sulfur were kneaded in a 1.8 liter closed mixer for 5 minutes, and when the temperature reached 135 ° C, the master batch was released. Obtained. The masterbatch was kneaded with a curing agent, a vulcanization accelerator and sulfur with an open roll to obtain a rubber composition. Using this rubber composition, unvulcanized physical properties (Mooney viscosity) were evaluated by the following test methods. The results are shown in Table I.
次に得られたゴム組成物を所定の金型中で１６０℃で２０分間加硫して加硫ゴムシートを調製し、以下に示す試験法で加硫ゴムの物性（硬度および破断伸び）を測定した。結果は表Ｉに示す。 Next, the obtained rubber composition was vulcanized in a predetermined mold at 160 ° C. for 20 minutes to prepare a vulcanized rubber sheet. The physical properties (hardness and elongation at break) of the vulcanized rubber were measured by the following test methods. It was measured. The results are shown in Table I.
ゴム物性評価試験法
ムーニー粘度（ＭＬ１＋４；１００℃）：ＪＩＳ Ｋ６３００に準拠して測定した。ムーニー粘度は、加工性の指標で低い方が加工性が良好であることを示す。
Rubber physical property evaluation test method Mooney viscosity (ML1 + 4; 100 ° C.): Measured according to JIS K6300. The Mooney viscosity is an index of processability, and the lower the Mooney viscosity, the better the processability.
硬度（Ｈｓ，２３℃）：ＪＩＳ Ｋ６２５３に準拠して測定した。この値が高い方が良好であることを示す。 Hardness (Hs, 23 ° C.): Measured according to JIS K6253. A higher value indicates better.
破断伸び（ＥＢ，２３℃）：ＪＩＳ Ｋ６２５１に準拠して測定した。この値が高い方が良好であることを示す。 Elongation at break (EB, 23 ° C.): Measured according to JIS K6251. A higher value indicates better.
表Ｉ脚注
＊１：ＴＳＲ２０
＊２：正同化学工業（株）製酸化亜鉛３種
＊３：日本油脂（株）製ビーズステアリン酸ＹＲ
＊４：キャボットジャパン（株）製ショウブラックＮ３３０Ｔ
＊５：東ソー・シリカ（株）製ニップシールＡＱ
Table I footnote * 1: TSR20
* 2: Three types of zinc oxide manufactured by Shodo Chemical Co., Ltd. * 3: Bead stearic acid YR manufactured by Nippon Oil & Fats Co., Ltd.
* 4: Show Black N330T manufactured by Cabot Japan Co., Ltd.
* 5: Tosoh Silica Co., Ltd. nip seal AQ
＊６：エポキシ樹脂１（ジャパンエポキシレジン（株）製エピコート１００１、軟化点６４℃、グリシジルエーテルタイプ（ビスＡ型））
＊７：エポキシ樹脂２（ジャパンエポキシレジン（株）製１５７Ｓ７０、軟化点７０℃、グリシジルエーテルタイプ（ノボラック型））
＊８：エポキシ樹脂３（ジャパンエポキシレジン（株）製エピコート１００７、軟化点１２８℃、グリシジルエーテルタイプ（ビスＡ型））
＊９：エポキシ樹脂４（東邦化成（株）製ＹＨ−４３４、グリシジルアミンタイプ、粘稠性樹脂）
＊１０：エポキシ樹脂５（ダイセル化学（株）製セロキサイド２０２１Ｐ、脂環式エポキシ樹脂、液状）
* 6: Epoxy resin 1 (Japan Epoxy Resin Co., Ltd. Epicoat 1001, softening point 64 ° C., glycidyl ether type (bis A type))
* 7: Epoxy resin 2 (157S70 manufactured by Japan Epoxy Resin Co., Ltd., softening point 70 ° C., glycidyl ether type (novolak type))
* 8: Epoxy resin 3 (Epicoat 1007 manufactured by Japan Epoxy Resin Co., Ltd., softening point 128 ° C., glycidyl ether type (bis A type))
* 9: Epoxy resin 4 (YH-434 manufactured by Toho Kasei Co., Ltd., glycidylamine type, viscous resin)
* 10: Epoxy resin 5 (Delcel Chemical Co., Ltd. Celoxide 2021P, alicyclic epoxy resin, liquid)
＊１１：昭和シェル石油（株）製デソレックス３号
＊１２：デグッサ社製Ｓｉ６９
＊１３：大内新興化学工業（株）製ノクセラーＮＳ−Ｐ
＊１４：鶴見化学工業（株）製金華印油入微粉硫黄
＊１５：硬化剤１（大内新興化学工業（株）製窒素含有アミン系硬化剤、三級環状アミン、ヘキサメチレンテトラミン、ノクセラーＨ）
＊１６：硬化剤２（新日本理化（株）製非窒素含有脂肪酸無水物、テトラヒドロ無水フタル酸、リカシッドＴＨ）
* 11: Desolex No. 3 manufactured by Showa Shell Sekiyu KK * 12: Si69 manufactured by Degussa
* 13: Noxeller NS-P manufactured by Ouchi Shinsei Chemical Co., Ltd.
* 14: Fine powder sulfur with Jinhua seal oil manufactured by Tsurumi Chemical Co., Ltd. * 15: Curing agent 1 (Nitrogen-containing amine-based curing agent, tertiary cyclic amine, hexamethylenetetramine, Noxeller H manufactured by Ouchi Shinsei Chemical Co., Ltd.)
* 16: Hardener 2 (Nippon Rika Co., Ltd. non-nitrogen-containing fatty acid anhydride, tetrahydrophthalic anhydride, Ricacid TH)
実施例１及び２では破断伸びと硬度をともに向上させ、かつ良好な加工性（低いムーニー粘度）を有するゴム組成物が得られる本発明例である。これに対し、比較例１はエポキシ樹脂が配合されていない従来例で、比較例２はグリシジルエーテルタイプのエポキシ樹脂を用いているがその軟化点が１００℃を超えるため硬度は上がるが、破断伸び及びムーニー粘度が劣る。比較例３及び４は異なるタイプのエポキシ樹脂を配合した例で、ムーニー粘度及び破断伸びは良くなるが、硬度が上がらない。比較例５は窒素を含まない硬化剤を用いた例でムーニー粘度は良好であるが、破断伸びが低下し、硬度の増大も認められない。 Examples 1 and 2 are examples of the present invention in which a rubber composition that improves both elongation at break and hardness and has good processability (low Mooney viscosity) is obtained. On the other hand, Comparative Example 1 is a conventional example in which no epoxy resin is blended, and Comparative Example 2 uses a glycidyl ether type epoxy resin, but its softening point exceeds 100 ° C., but the hardness increases, but elongation at break. And Mooney viscosity is inferior. Comparative Examples 3 and 4 are examples in which different types of epoxy resins are blended. Mooney viscosity and elongation at break are improved, but hardness is not increased. Comparative Example 5 is an example using a curing agent that does not contain nitrogen and has a good Mooney viscosity, but the elongation at break decreases and no increase in hardness is observed.
以上の通り、従来はゴムの硬度を上げると破断伸びが低下し、硬度を上げながら、同時に破断伸びを向上させることは困難とされてきたが、本発明によれば、特定のエポキシ樹脂と硬化剤を配合することによって、ゴムの破断伸びと硬度をともに向上させ、かつ良好な加工性を有するタイヤ用ゴム組成物が得られ、空気入りタイヤのトレッド、ビードフィラーなどに使用するのに好適である。 As described above, conventionally, when the hardness of rubber is increased, the elongation at break decreases, and it has been difficult to improve the elongation at the same time while increasing the hardness. By blending an agent, a rubber composition for a tire that improves both the elongation and hardness of rubber and has good processability is obtained, which is suitable for use in a tread of a pneumatic tire, a bead filler, and the like. is there.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2951182A1 (en) * | 2009-10-14 | 2011-04-15 | Michelin Soc Tech | RUBBER COMPOSITION COMPRISING AN EPOXY RESIN |
| WO2014016344A1 (en) * | 2012-07-25 | 2014-01-30 | Compagnie Generale Des Etablissements Michelin | Rubber composition comprising a lignin-based resin |
| WO2014016346A1 (en) * | 2012-07-25 | 2014-01-30 | Compagnie Generale Des Etablissements Michelin | Rubber composition comprising an epoxy resin and a polyimine hardener |
| WO2014022199A1 (en) * | 2012-07-31 | 2014-02-06 | Bridgestone Americas Tire Operations, Llc | Tire with laminate |
| FR2995314A1 (en) * | 2012-12-12 | 2014-03-14 | Michelin & Cie | Rubber composition, useful in a semi-finished product and a pneumatic tire, comprises epoxy resin comprising a pattern having an aromatic ring and/or an unsaturated aliphatic chain, where the composition is devoid of an amine hardener |
| WO2015100029A1 (en) * | 2013-12-23 | 2015-07-02 | Bridgestone Americas Tire Operations, Llc | Tire with reinforced tread |
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2006
- 2006-12-11 JP JP2006333130A patent/JP2008144044A/en active Pending
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2951182A1 (en) * | 2009-10-14 | 2011-04-15 | Michelin Soc Tech | RUBBER COMPOSITION COMPRISING AN EPOXY RESIN |
| WO2011045342A1 (en) * | 2009-10-14 | 2011-04-21 | Societe De Technologie Michelin | Rubber composition including an epoxide resin |
| CN102575068A (en) * | 2009-10-14 | 2012-07-11 | 米其林技术公司 | Rubber composition including an epoxide resin |
| KR20120098615A (en) * | 2009-10-14 | 2012-09-05 | 꽁빠니 제네날 드 에따블리세망 미쉘린 | Rubber composition including an epoxide resin |
| JP2013507507A (en) * | 2009-10-14 | 2013-03-04 | コンパニー ゼネラール デ エタブリッスマン ミシュラン | Rubber composition containing epoxide resin |
| KR101692572B1 (en) * | 2009-10-14 | 2017-01-03 | 꽁빠니 제네날 드 에따블리세망 미쉘린 | Rubber composition including an epoxide resin |
| RU2554633C2 (en) * | 2009-10-14 | 2015-06-27 | Компани Женераль Дез Этаблиссман Мишлен | Rubber composition, containing epoxy resin |
| US8877839B2 (en) | 2009-10-14 | 2014-11-04 | Compagnie Generale Des Etablissements Michelin | Rubber composition including an expoxide resin |
| FR2993892A1 (en) * | 2012-07-25 | 2014-01-31 | Michelin & Cie | RUBBER COMPOSITION COMPRISING AN EPOXY RESIN AND A POLY-IMINE HARDENER |
| FR2993895A1 (en) * | 2012-07-25 | 2014-01-31 | Michelin & Cie | RUBBER COMPOSITION COMPRISING A LIGNIN-BASED RESIN |
| WO2014016346A1 (en) * | 2012-07-25 | 2014-01-30 | Compagnie Generale Des Etablissements Michelin | Rubber composition comprising an epoxy resin and a polyimine hardener |
| JP2015528845A (en) * | 2012-07-25 | 2015-10-01 | コンパニー ゼネラール デ エタブリッスマン ミシュラン | Rubber composition comprising epoxy resin and polyimine curing agent |
| WO2014016344A1 (en) * | 2012-07-25 | 2014-01-30 | Compagnie Generale Des Etablissements Michelin | Rubber composition comprising a lignin-based resin |
| US9714339B2 (en) | 2012-07-25 | 2017-07-25 | Compagnie Generale Des Etablissements Michelin | Rubber composition comprising an epoxy resin and a polyimine hardener |
| WO2014022199A1 (en) * | 2012-07-31 | 2014-02-06 | Bridgestone Americas Tire Operations, Llc | Tire with laminate |
| CN104507709A (en) * | 2012-07-31 | 2015-04-08 | 普利司通美国轮胎运营有限责任公司 | Tire with laminate |
| FR2995314A1 (en) * | 2012-12-12 | 2014-03-14 | Michelin & Cie | Rubber composition, useful in a semi-finished product and a pneumatic tire, comprises epoxy resin comprising a pattern having an aromatic ring and/or an unsaturated aliphatic chain, where the composition is devoid of an amine hardener |
| WO2015100029A1 (en) * | 2013-12-23 | 2015-07-02 | Bridgestone Americas Tire Operations, Llc | Tire with reinforced tread |
| US10160265B2 (en) | 2013-12-23 | 2018-12-25 | Bridgestone Americas Tire Operations, Llc | Tire with reinforced tread |
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