JPH0699600B2 - Rubber composition - Google Patents
Rubber compositionInfo
- Publication number
- JPH0699600B2 JPH0699600B2 JP62170160A JP17016087A JPH0699600B2 JP H0699600 B2 JPH0699600 B2 JP H0699600B2 JP 62170160 A JP62170160 A JP 62170160A JP 17016087 A JP17016087 A JP 17016087A JP H0699600 B2 JPH0699600 B2 JP H0699600B2
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- weight
- petroleum resin
- cyclopentadiene
- rubber composition
- Prior art date
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Description
【発明の詳細な説明】 （産業上の利用分野） 本発明はシクロペンタジエン系石油樹脂30〜90重量部と
C5系脂肪族石油樹脂70〜10重量部との石油樹脂混合物か
らなるゴム用配合材をジエン系重合体に配合し、特にタ
イヤトレッド部の耐カット性、耐チップ性を著るしく改
善するとともに、優れた粘着力を付与したゴム組成物に
関するものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial field of application) The present invention relates to a cyclopentadiene-based petroleum resin in an amount of 30 to 90 parts by weight.
The rubber compounding material composed of a petroleum resin mixture of C 5 based aliphatic petroleum resin 70 to 10 parts by weight blended with diene polymer, in particular Silurian properly improve cut resistance of the tire tread portion, a chip resistance The present invention also relates to a rubber composition having excellent adhesive strength.
高速バスやトラック等の大型タイヤや土木建設用等のOT
R（Off The Road）タイヤは通常過酷な条件下で使用さ
れるため、これらのタイヤには常に高荷重の負荷が発生
し、特に岩石等との衝突によりタイヤトレッド部のカッ
ティングやチッピングがしばしば生じ安全上の問題とな
っている。OT for large tires such as high-speed buses and trucks and civil engineering construction
Since R (Off The Road) tires are usually used under severe conditions, these tires are constantly subjected to high loads, and cutting and chipping of the tire tread often occur especially due to collision with rocks. It is a safety issue.
（従来の技術） これらの耐カット性および耐チップ性の改良開発は古く
から行われ、天然ゴム、スチレン−ブタジエンゴム（SB
R）等の最適なジエン系重合体の選択あるいはシクロペ
ンタジエン類を主成分とする石油樹脂を補強材として添
加する方法が提唱されている。(Prior art) These cut resistance and chip resistance have been improved for a long time, and natural rubber and styrene-butadiene rubber (SB
A method of selecting an optimal diene polymer such as R) or adding a petroleum resin containing cyclopentadiene as a main component as a reinforcing material has been proposed.
特公昭48−38615号はシクロペンタジエン系樹脂を、特
公昭52−43664号ではフェノール樹脂で変性したシクロ
ペンタジエン樹脂を、また特公昭58−18938号ではシク
ロペンタジエン−オキシスチレン共重合体をそれぞれSB
Rあるいは天然ゴムに配合することによってタイヤトレ
ッド部の耐カット性および耐チップ性を改良できること
を各々開示している。JP-B-48-38615 is a cyclopentadiene-based resin, JP-B-52-43664 is a cyclopentadiene resin modified with a phenol resin, and JP-B-58-18938 is a cyclopentadiene-oxystyrene copolymer.
It discloses that cutting resistance and chip resistance of the tire tread portion can be improved by blending with R or natural rubber.
本発明者らもさらに優れた耐カット性および耐チップ性
を示すシクロペンタジエン系石油樹脂を配合するゴム組
成物について種々の方法を開示してきた（特開昭61−14
8249号、特開昭62−295933号）。しかし、これらのシク
ロペンタジエン系石油樹脂類を配合したゴム組成物は優
れた耐カット性および耐チップ性を示すものの、未加硫
時の粘着性が低いので、タイヤ製造時にタイヤトレッド
部の原料として加工上の問題を残すばかりか、タイヤの
その他の部分、例えばサイドウォール、カーカス部等へ
の適用も限定されるという欠点があった。一方、C5系脂
肪族石油樹脂あるいはC9系芳香族石油樹脂を配合したゴ
ム組成物は、優れた粘着性を示すものの、耐カット性お
よび耐チップ性においてはシクロペンタジエン系石油樹
脂を配合した場合に比べて極めて低いという欠点があっ
た。The present inventors have also disclosed various methods for a rubber composition containing a cyclopentadiene-based petroleum resin exhibiting further excellent cut resistance and chip resistance (JP-A-61-14).
8249, JP-A-62-295933). However, although rubber compositions containing these cyclopentadiene-based petroleum resins show excellent cut resistance and chip resistance, they have low tackiness when not vulcanized, and thus are used as raw materials for tire tread parts during tire production. In addition to leaving a processing problem, there is a drawback that the application to other parts of the tire, such as sidewalls and carcass parts, is limited. On the other hand, a rubber composition containing a C 5 type aliphatic petroleum resin or a C 9 type aromatic petroleum resin shows excellent tackiness, but a cyclopentadiene type petroleum resin was added in terms of cut resistance and chip resistance. It had the drawback of being extremely low compared to the case.
（解決しようとする問題点） 本発明の目的は優れた耐カット性および耐チップ性とと
もに優れた粘着性を同時に示すゴム組成物を提供するこ
とにある。(Problems to be Solved) An object of the present invention is to provide a rubber composition which simultaneously exhibits excellent cut resistance and chip resistance, and also excellent adhesiveness.
高速度あるいは高荷重で回転するタイヤトレッド部の岩
石等との衝突あるいは摩擦等に対する耐カット性あるい
は耐チップ性を評価するには、実走行テストやミニチュ
アータイヤによるシュミレーションテストあるいは衝撃
カット試験等複雑な実用性能試験が必要であり、多大な
費用、労力および時間を必要とする。しかし、前記３件
の公告公報等に該性能の実験室評価法として引張試験法
が教示されており、しかもこの試験法が実用性能と良く
相関することも確認されている。引張試験はゴム組成物
の弾性エネルギー特性を示す方法である。タイヤトレッ
ド部のカッティングおよびチッピングの発生度合が岩石
等との衝突等により生じるエネルギーをタイヤトレッド
部がどれ程吸収するかで左右されることを考えると該試
験法はよく理解される方法である。To evaluate the cut resistance or chip resistance against collision or friction with rocks etc. of the tire tread that rotates at high speed or high load, it is necessary to perform complicated tests such as an actual running test, a simulation test with a miniature tire, or an impact cut test. Practical performance test is required, and it requires a great deal of expense, labor and time. However, the tensile test method is taught as a laboratory evaluation method of the performance in the above-mentioned three publications, and it is also confirmed that this test method correlates well with practical performance. The tensile test is a method of showing the elastic energy characteristics of a rubber composition. The test method is well understood considering that the degree of occurrence of cutting and chipping of the tire tread portion depends on how much the tire tread portion absorbs energy generated by collision with rocks and the like.
したがって換言するならば本発明の目的はより大きな弾
性エネルギー特性すなわち、常温および高温（100℃）
でより大きな応力値と特に優れた伸びを示すとともに、
優れた粘着性を有するゴム組成物を提供することにあ
る。タイヤは、使用時に繰り返して受ける応力によて発
熱するので、常温時の特性に較べて高温時の特性の方が
さらに重要である。Therefore, in other words, the object of the present invention is to obtain a larger elastic energy characteristic, that is, room temperature and high temperature (100 ° C.)
Shows a larger stress value and particularly excellent elongation at
It is to provide a rubber composition having excellent tackiness. Since the tire generates heat due to the stress repeatedly applied during use, the characteristics at high temperature are more important than the characteristics at normal temperature.
（問題点を解決するための手段） 本発明者らは種々のゴム組成物用石油樹脂について鋭意
検討を重ね、開発改良を行った結果、シクロペンタジエ
ン系石油樹脂30〜90重量部とC5系脂肪族石油樹脂70〜10
重量部との石油樹脂混合物をジエン系重合体に配合する
と、これらの樹脂を個々に配合する時を上回る大きな応
力値および伸びと共に高い粘着性を示すことから、優れ
た配合効果があることを見い出し本発明を完成した。(Means for Solving Problems) The inventors of the present invention have conducted extensive studies on various petroleum resins for rubber compositions and made development and improvement. As a result, 30 to 90 parts by weight of a cyclopentadiene-based petroleum resin and C 5 system are used. Aliphatic petroleum resin 70 to 10
It has been found that when a petroleum resin mixture with parts by weight is blended with a diene polymer, a high stress value and elongation as well as high tackiness, which are higher than when these resins are blended individually, and high tackiness are exhibited, and that there is an excellent blending effect. The present invention has been completed.
すなわち、本発明は、シクロペンタジエン系熱重合石油
樹脂30〜90重量部とC5系脂肪族カチオン重合石油樹脂70
〜10重量部との石油樹脂混合物からなる配合材を、ジエ
ン系重合体100重量部に対して５〜40重量部配合してな
るゴム組成物を提供することにある。That is, the present invention comprises 30 to 90 parts by weight of a cyclopentadiene-based thermally polymerized petroleum resin and a C 5 -based aliphatic cation-polymerized petroleum resin 70.
It is to provide a rubber composition comprising 5 to 40 parts by weight of a compounding material composed of a petroleum resin mixture with 10 to 10 parts by weight with respect to 100 parts by weight of a diene polymer.
以下に本発明をさらに詳細に記載する。The present invention is described in more detail below.
本発明の組成物を構成する配合材の一つの構成成分のシ
クロペンタジエン系石油樹脂としてはナフサのスチーム
クラッキング等から得られるシクロペンタジエンあるい
はジシクロペンタジエンあるいはこれらのアルキル置換
体またはこれらの混合物等のシクロペンタジエン類の熱
重合樹脂あるいはこれらのシクロペンタジエン類と鎖状
α−オレフィン、鎖状ジオレフィンさらにはビニル芳香
族化合物等の共単量体、あるいはこれらの混合物との熱
共重合樹脂があげられる。熱重合は通常の方法で溶剤の
存在下あるいは不存在下に220〜320℃の温度で行われ
る。さらにこれらの共単量体を存在させる場合、その量
はシクロペンタジエン類100重量部あたりそれぞれ100重
量部未満配合されることが好ましい。The cyclopentadiene-based petroleum resin, which is one of the constituents of the compounding material constituting the composition of the present invention, is cyclopentadiene or dicyclopentadiene obtained from naphtha steam cracking or the like, or an alkyl-substituted product thereof or a mixture thereof, or the like. Examples thereof include thermopolymerization resins of pentadiene compounds, or cyclopentadiene compounds and chain α-olefins, chain diolefins, comonomers such as vinyl aromatic compounds, and heat copolymerization resins of mixtures thereof. The thermal polymerization is carried out in the usual manner in the presence or absence of a solvent at a temperature of 220 to 320 ° C. Further, when these comonomers are present, the amount thereof is preferably less than 100 parts by weight per 100 parts by weight of cyclopentadiene.
また、本発明で用いる配合材のもう１つの構成成分のC5
系脂肪族石油樹脂はナフサのスチームクラッキング等で
得られるC5留分中に含まれるイソプレンあるいはピペリ
レン等の脂肪族系ジオレフィンをAlCl3等のフリーデル
クラフト型触媒を用い０〜90℃の温度範囲でカチオン重
合して得られる。なおこれらの石油樹脂はゴムへの配合
温度および保存時のブロッキング等を考慮するなら80〜
150℃の軟化点を示すものが好ましい。C 5 which is another constituent of the compounding material used in the present invention
Aliphatic petroleum resins are aliphatic diolefins such as isoprene or piperylene contained in the C 5 fraction obtained by steam cracking of naphtha, etc., using a Friedel-Craft type catalyst such as AlCl 3 at a temperature of 0 to 90 ° C. It is obtained by cationic polymerization in the range. These petroleum resins should be 80-80 if considering the compounding temperature in rubber and blocking during storage.
Those having a softening point of 150 ° C. are preferable.
このようにして得られたシクロペンタジエン系石油樹脂
とC5系脂肪族石油樹脂の混合物が本発明で用いる配合材
であって、シクロペンタジエン系石油樹脂30〜90重量部
とC5系脂肪族石油樹脂70〜10重量部の混合物である。前
記以外の混合範囲では両者の長所すなわち優れた耐カッ
ト性、耐チップ性および粘着性をジエン系重合体に同時
に発現させることができない。本発明のゴム組成物は、
この混合物を配合材としてジエン系重合体に配合したも
のであって、その配合量はジエン系重合体100重量部あ
たり一般に５〜40重量部、好ましくは５〜20重量部の割
合である。しかし、特殊用途に使用されるタイヤ、例え
ば特殊な自動二輪車や競争用自動車用タイヤ、について
は本発明の配合材を前記範囲より大量に使用することも
できる。A mixture of the cyclopentadiene-based petroleum resin and the C 5 -based aliphatic petroleum resin thus obtained is a compounding material used in the present invention, wherein 30 to 90 parts by weight of the cyclopentadiene-based petroleum resin and the C 5 -based aliphatic petroleum are used. It is a mixture of 70 to 10 parts by weight of resin. In the mixing range other than the above range, the advantages of both, that is, the excellent cut resistance, chip resistance and tackiness cannot be simultaneously exhibited in the diene polymer. The rubber composition of the present invention is
This mixture is blended with a diene polymer as a blending material, and the blending amount is generally 5 to 40 parts by weight, preferably 5 to 20 parts by weight per 100 parts by weight of the diene polymer. However, for tires used for special purposes, such as special motorcycle tires and competitive automobile tires, the compounding material of the present invention can be used in a larger amount than the above range.
また本発明の「ジエン系重合体」には天然ゴムやポリブ
タジエンゴム、スチレン−ブタジエンゴム、イソプレン
ゴム等の合成ゴムやそれらの混合物が含まれる。The "diene polymer" of the present invention includes synthetic rubbers such as natural rubber, polybutadiene rubber, styrene-butadiene rubber, isoprene rubber, and mixtures thereof.
（発明の効果） 本発明のゴム組成物は、耐カット性および耐チップ性に
優れたシクロペンタジエン系石油樹脂と粘着性に優れた
C5系脂肪族石油樹脂とを特定比率で配合することによ
り、シクロペンタジエン系石油樹脂を単独で配合する場
合を上回る耐カット性および耐チップ性を示すとともに
粘着性も約２〜３倍向上し、耐カット性、耐チップ性お
よび粘着性のすべてにおいて相乗的な配合効果を生ずる
ので、タイヤトレッド部の原料として極めて好適であ
り、またタイヤのサイドウォール、カーカス部等への適
用も可能となって使用範囲が拡大される等の優れた特性
を有する。さらに、本発明の配合材は、構成成分の石油
樹脂を熱重合またはカチオン重合により極めて簡単に製
造することができ、また、単に混合するだけで容易に調
整することができるものである。(Effect of the Invention) The rubber composition of the present invention has excellent adhesiveness with cyclopentadiene-based petroleum resin having excellent cut resistance and chip resistance.
By blending with a C 5 -based aliphatic petroleum resin in a specific ratio, it exhibits cut resistance and chip resistance higher than when cyclopentadiene-based petroleum resin is blended alone, and the tackiness is also improved by about 2 to 3 times. Since it produces a synergistic compounding effect in all of cut resistance, chip resistance and tackiness, it is extremely suitable as a raw material for tire tread parts, and can be applied to tire sidewalls, carcass parts, etc. It has excellent characteristics such as widening the range of use. Further, the blending material of the present invention can be produced very easily by heat or cationic polymerization of the petroleum resin as a constituent component, and can be easily adjusted by simply mixing.
（実施例） 以下実施例などにより本発明をさらに具体的に説明する
のがこれらによって本発明が限定されるものではない。(Examples) The present invention will be described in more detail with reference to the following examples, which should not be construed as limiting the present invention.
ここで、ゴム配合処方は第１表に示すとおり標準的なも
のを採用した。配合割合は全て重量部である。Here, as the rubber compounding recipe, standard ones were adopted as shown in Table 1. All compounding ratios are parts by weight.
ゴム組成物はロール方式でJIS K6383に従って混合調整
し引張試験はJISK6301に準拠して測定評価した。粘着性
は未加硫生地シートを500gf（グラフ重）で30秒間圧着
した後の粘着力をピックアップ式タックメーターで測定
して評価した。The rubber composition was mixed and adjusted according to JIS K6383 by a roll method, and the tensile test was measured and evaluated according to JIS K6301. The tackiness was evaluated by pressing the unvulcanized fabric sheet at 500 gf (graph weight) for 30 seconds and measuring the tackiness with a pickup type tack meter.
参考例１ ナフサのスチームクラッキングから得られたシクロペン
タジエン類の濃度が75.0重量％のシクロペンタジエン系
原料700gと同様にナフサのスチームクラッキングから得
られたスチレン、ビニルトルエン、α−およびβ−メチ
ルスチレンおよびインデンを26.5重量％含む、芳香族留
分300gを内容積2lのオートクレーブに仕込み、窒素雰囲
気下で攪拌しながら280℃で２時間保持し重合した。引
続き減圧下で未反応原料、オリゴマー等を除去した後軟
化点105℃のシクロペンタジエン系樹脂I 706gを得た。 Reference Example 1 Similar to 700 g of cyclopentadiene-based raw material having a cyclopentadiene concentration of 75.0% by weight obtained from steam cracking of naphtha, styrene, vinyltoluene, α- and β-methylstyrene obtained from steam cracking of naphtha and 300 g of an aromatic fraction containing 26.5% by weight of indene was charged into an autoclave having an internal volume of 2 l, and the mixture was maintained at 280 ° C. for 2 hours with stirring under a nitrogen atmosphere to carry out polymerization. Subsequently, unreacted raw materials, oligomers and the like were removed under reduced pressure, and 706 g of cyclopentadiene resin I having a softening point of 105 ° C. was obtained.
参考例２ 参考例１で用いたシクロペンタジエン系原料700gとイソ
ブチレンから誘導した2,4,4−トリメチルペンテン−１
を75.4重量％含むジイソブチレン200gを参考例１と同じ
方法で260℃、３時間保持し、重合した。その後未反応
原料、オリゴマー等を除去し軟化点が99℃のシクロペン
タジエン系樹脂IIを651g得た。Reference Example 2 2,4,4-trimethylpentene-1 derived from 700 g of the cyclopentadiene raw material used in Reference Example 1 and isobutylene
In the same manner as in Reference Example 1, 200 g of diisobutylene containing 75.4% by weight was held at 260 ° C. for 3 hours for polymerization. Then, unreacted raw materials, oligomers and the like were removed to obtain 651 g of cyclopentadiene resin II having a softening point of 99 ° C.
参考例３ ナフサのスチームクラッキングから得られたピペリレン
を主体としたジエン濃度が23.0重量％のC5系留分100gを
約85℃でAlCl3・酢酸メチル触媒を用いカチオン重合し
た。重合液を中和水洗し触媒を除去した後、未反応原
料、オリゴマー等を除去し軟化点が102℃のC5系脂肪族
石油脂肪25gを得た。Reference Example 3 100 g of a C 5 -based fraction mainly composed of piperylene obtained from steam cracking of naphtha and having a diene concentration of 23.0% by weight was subjected to cationic polymerization at about 85 ° C. using an AlCl 3 / methyl acetate catalyst. After the polymerization liquid was washed with neutralized water to remove the catalyst, unreacted raw materials, oligomers and the like were removed to obtain 25 g of C 5 aliphatic petroleum fat having a softening point of 102 ° C.
比較例１〜４、実施例１〜３ 参考例１〜３で得た石油樹脂をジエン系重合体（SBR）1
00重量部あたり０〜10重量部の範囲でそれぞれ配合しゴ
ム組成物を得た。これらのゴム組成物の性能を測定した
結果を第１および２図に示し、かつそのうちの代表的な
データを比較例１〜４および実施例１〜３として第２表
に示す。Comparative Examples 1 to 4 and Examples 1 to 3 The petroleum resins obtained in Reference Examples 1 to 3 were used as a diene polymer (SBR) 1
A rubber composition was obtained by mixing each in an amount of 0 to 10 parts by weight per 00 parts by weight. The results of measuring the performance of these rubber compositions are shown in FIGS. 1 and 2, and the representative data thereof are shown in Table 2 as Comparative Examples 1 to 4 and Examples 1 to 3.
比較例１は石油樹脂を含まないブランクを、また比較例
２、３は参考例１および３で得た樹脂をそれぞれ単独で
10重量部配合した時の例を各々示す。比較例２では十分
な伸びを示すもののその粘着力の改善に全く効果が認め
られない。逆に比較例３では大きな粘着力を示すものの
伸びの改善効果は小さい。比較例４のような本発明の請
求範囲外の配合量では十分な伸びを示さず、優れた伸び
と粘着力を同時に付与したゴム組成物が得られない。Comparative Example 1 was a blank containing no petroleum resin, and Comparative Examples 2 and 3 were the resins obtained in Reference Examples 1 and 3, respectively.
Examples of 10 parts by weight are shown below. In Comparative Example 2, although sufficient elongation is exhibited, no effect is recognized in improving the adhesive strength. On the contrary, Comparative Example 3 shows a large adhesive force, but the effect of improving elongation is small. With a compounding amount outside the claimed range of the present invention as in Comparative Example 4, sufficient elongation is not exhibited, and a rubber composition having excellent elongation and adhesive strength at the same time cannot be obtained.
実施例１〜３に示すように本発明に従って配合した場合
のみ十分な伸びと粘着力を示すバランスのとれたゴム配
合物が得られる。なお、これらの値はシクロペンタジエ
ン系石油樹脂およびC5系脂肪族石油樹脂を各々単独に配
合した時の添加効果値を加算した値より大きく、両者を
混合配合することによる相乗効果が第１図および第２図
から認められる。As shown in Examples 1 to 3, only when compounded according to the present invention, a well-balanced rubber compound showing sufficient elongation and adhesive strength can be obtained. Note that these values are larger than the sum of the additive effect values when cyclopentadiene-based petroleum resin and C 5 aliphatic hydrocarbon resin are individually blended, and the synergistic effect of blending both is shown in FIG. And from FIG.
なお、加算添加効果値をＣとし、C5系脂肪族石油樹脂の
単独添加効果値をＡとし、シクロペンタジエン系石油樹
脂の単独添加効果値をＢとすればＣ＝Ａ＋Ｂである。C = A + B, where C is the additive effect value, C is the additive effect value of the C 5 -based aliphatic petroleum resin, and B is the additive effect value of the cyclopentadiene-based petroleum resin.
第１図は、本発明に係るゴム組成物の樹脂配合量と伸び
との関係を示すグラフであり、そして第２図は樹脂配合
量と粘着力との関係を示すグラフである。 樹脂配合量はSBR100重量部当りの配合量である。 Ｉ……混合石油樹脂、II……加算添加効果値、 III……シクロペンタジエン系石油樹脂Ｉ単独添加、 IV……C5系脂肪族石油樹脂単独添加、 Ｏ……実施例、×……比較例FIG. 1 is a graph showing the relationship between the resin content and the elongation of the rubber composition according to the present invention, and FIG. 2 is a graph showing the relationship between the resin content and the adhesive strength. The resin compounding amount is the compounding amount per 100 parts by weight of SBR. I ...... mixed petroleum resin, II ...... sum effect of addition values, III ...... cyclopentadiene petroleum resin I added alone, IV ...... C 5 based aliphatic petroleum resin alone added, O ...... embodiment, × ...... Comparison An example
Claims (1)
90重量部とC5系脂肪族カチオン重合石油樹脂70〜10重量
部との石油樹脂混合物からなる配合材を、ジエン系重合
体100重量部に対して５〜40重量部配合してなるゴム組
成物。1. A cyclopentadiene-based thermally polymerized petroleum resin 30 to
A rubber composition obtained by compounding 5 to 40 parts by weight of a compounding material comprising a petroleum resin mixture of 90 parts by weight and a C 5 -based aliphatic cation-polymerized petroleum resin 70 to 10 parts by weight with respect to 100 parts by weight of a diene polymer. object.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62170160A JPH0699600B2 (en) | 1987-07-08 | 1987-07-08 | Rubber composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62170160A JPH0699600B2 (en) | 1987-07-08 | 1987-07-08 | Rubber composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6414259A JPS6414259A (en) | 1989-01-18 |
| JPH0699600B2 true JPH0699600B2 (en) | 1994-12-07 |
Family
ID=15899794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62170160A Expired - Fee Related JPH0699600B2 (en) | 1987-07-08 | 1987-07-08 | Rubber composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0699600B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03110167A (en) * | 1989-09-25 | 1991-05-10 | Toyo Seikan Kaisha Ltd | Ultraviolet irradiation type metal plate multicolor printing line |
| JPH0488066A (en) * | 1990-07-30 | 1992-03-19 | Sekisui Chem Co Ltd | Primer composition and resin-coated metal |
| CA2292925A1 (en) * | 1999-02-16 | 2000-08-16 | The Goodyear Tire & Rubber Company | Polymeric resinous material derived from limonene, dicyclopentadiene, indene and vinyl toluene |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4838615A (en) * | 1971-09-17 | 1973-06-07 | ||
| JPS52112639A (en) * | 1976-03-19 | 1977-09-21 | Sumitomo Chem Co Ltd | Pressure sensitive adhesive composition |
| JPS55152731A (en) * | 1979-05-16 | 1980-11-28 | Sumitomo Chem Co Ltd | Rubber composition |
| JPS61148249A (en) * | 1984-12-21 | 1986-07-05 | Maruzen Sekiyu Kagaku Kk | Rubber composition and additive therefor |
| JPH0689182B2 (en) * | 1985-02-19 | 1994-11-09 | 株式会社ブリヂストン | Rubber composition with improved cut resistance and chipping resistance |
-
1987
- 1987-07-08 JP JP62170160A patent/JPH0699600B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6414259A (en) | 1989-01-18 |
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| LAPS | Cancellation because of no payment of annual fees |