JPH05262920A - Rubber formulating agent - Google Patents
Rubber formulating agentInfo
- Publication number
- JPH05262920A JPH05262920A JP9220092A JP9220092A JPH05262920A JP H05262920 A JPH05262920 A JP H05262920A JP 9220092 A JP9220092 A JP 9220092A JP 9220092 A JP9220092 A JP 9220092A JP H05262920 A JPH05262920 A JP H05262920A
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- vulcanization
- agent
- aminodiphenylamine
- molecular weight
- Prior art date
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、特に加硫促進剤として
有効に使用される高分子量で低毒性のゴム配合剤に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a high molecular weight and low toxicity rubber compounding agent which is effectively used as a vulcanization accelerator.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】近年、
従来の加硫促進剤を用いたタイヤ及び工業用ゴム製品の
加硫工程や使用時に発癌性のあるニトロソアミンが発生
するという問題がクローズアップされてきた。また、ハ
ロゲン系ゴムに使用されているエチレンチオウレアは、
発癌性に問題があるとして、厚生省告示第８５号で食品
用途への使用が禁止されている。更に、現在利用度の多
い主要加硫促進剤の一つである２ーメルカプトベンゾチ
アゾール（ＭＢＴ）も将来的には発癌性や毒性の問題か
ら使用できなくなると報告されている。2. Description of the Related Art In recent years,
The problem that nitrosamine, which has carcinogenicity, is generated during the vulcanization process and use of tires and industrial rubber products using conventional vulcanization accelerators has been highlighted. In addition, ethylene thiourea used in halogen rubber is
Due to the problem of carcinogenicity, its use in foods is prohibited by Ministry of Health and Welfare Notification No. 85. Furthermore, it has been reported that 2-mercaptobenzothiazole (MBT), which is one of the main vulcanization accelerators currently in widespread use, cannot be used in the future due to carcinogenicity and toxicity.
【０００３】一方、労働安全衛生法第５７条の２項では
数平均分子量が２０００以上の高分子化合物は、既存の
化学物質として取り扱う旨規定されており、また、米国
環境保護庁では、数平均分子量が１０００以上の高分子
化合物は、既存の物質として取り扱うことが定められて
いる。このように配合剤の数平均分子量が１０００〜２
０００以上の化合物であれば有害性の問題はなく、しか
もゴムに配合した場合、配合時分散剤、可塑剤、スコー
チ防止剤等の役割を果たす可能性もあり、その上加硫物
は高分子網目がお互いに入り組みからみ合う相互侵入網
目（ＩＰＮ）が形成される機能性付与剤としての役割も
期待できる。On the other hand, Article 57-2 of the Occupational Safety and Health Act stipulates that polymer compounds having a number average molecular weight of 2000 or more should be treated as existing chemical substances, and the US Environmental Protection Agency has a number average number. It is stipulated that a polymer compound having a molecular weight of 1000 or more should be handled as an existing substance. Thus, the number average molecular weight of the compounding agent is 1000 to 2
If it is a compound of 000 or more, there is no problem of toxicity, and when compounded into rubber, it may play a role of a dispersant, a plasticizer, an anti-scorch agent, etc. at the time of compounding. It can also be expected to play a role as a functionality-imparting agent for forming an interpenetrating network (IPN) in which the meshes mesh with each other and are entangled with each other.
【０００４】このため、従来より高分子量加硫剤や高分
子量加硫促進剤がいくつか研究されている。例えば、高
分子量加硫促進剤に関し、アドヒカリらは、高分子量チ
オカルバミルスルフェンアミドを合成し、天然ゴムの加
硫促進剤になることを報告している（Ｊ．Ｐｏｌｙｍ．
Ｍａｔｅｒ．，１，（２），１１０（１９８４））。カ
ムライらは、ジアミン、二硫化炭素及び水酸化ナトリウ
ムの反応後、よう素で酸化して高分子量のポリチオカル
バモイルスルフェンアミドを合成し、天然ゴムへの添加
で促進効果があることを報告している（Ｋａｕｔｓｃ
ｈ．Ｇｕｍｍｉ，Ｋｕｎｎｓｔｓｔ．，４０，（８），
７５２（１９８７）。イスマイルらは、エポキシ化アマ
ニ油とアニリン及びフェニルヒドラジンを反応させ、高
分子量の開環アマニ油を合成し、天然ゴムに加硫能があ
ることを報告している（Ｒｕｂｂｅｒ Ｗｏｒｌｄ，Ｏ
ｃｔｏｂｅｒ，３７（１９８７））。Therefore, some studies have been conducted on high molecular weight vulcanizing agents and high molecular weight vulcanization accelerators. For example, regarding a high molecular weight vulcanization accelerator, Adhikari et al. Have reported that a high molecular weight thiocarbamylsulfenamide is synthesized to be a vulcanization accelerator for natural rubber (J. Polym.
Mater. , 1, (2), 110 (1984)). Kamurai et al. Reported that after the reaction of diamine, carbon disulfide and sodium hydroxide, they were oxidized with iodine to synthesize high molecular weight polythiocarbamoylsulfenamide, and the addition to natural rubber had a promoting effect. There is (Kautsc
h. Gummi, Kunnstst. , 40, (8),
752 (1987). Ismail et al. Reported that epoxidized linseed oil was reacted with aniline and phenylhydrazine to synthesize a high molecular weight ring-opened linseed oil, and natural rubber had vulcanizing ability (Rubber World, O.
ctber, 37 (1987)).
【０００５】しかしながら、これらのものはＳＢＲの老
化防止剤あるいは可塑剤となるが、加硫促進能力は小さ
い。[0005] However, these are SBR antioxidants or plasticizers, but their vulcanization accelerating ability is small.
【０００６】また、最近川口化学工業（株）は、２−メ
ルカプトベンゾチアゾールの塩素化物とポリエーテルジ
メルカプタンから液状の高分子量ポリスルフィドを合成
し、天然ゴムなどのジエン系ゴムの加硫促進剤となるこ
とを報告している（特開昭６２ー１００５４２号公
報）。更に、コーランらは、２ービニルピリジン及び４
ービニルピリジンとブタジエンの乳化重合で高分子量の
ポリビニルピリジン共重合体を合成し、ＳＢＲの共活性
剤となることを報告している（Ｐｌａｓｔ．Ｒｕｂｂｅ
ｒ Ｐｒｏｃｅｓｓ．Ａｐｐｌ．，１２，（２），８１
（１９８９）；Ｒｕｂｂｅｒ Ｃｈｅｍ．Ｔｅｃｈｎｏ
ｌ．，６２，（５），９５７（１９８９））が、天然ゴ
ムには効果がない。Recently, Kawaguchi Chemical Industry Co., Ltd. has synthesized a liquid high-molecular-weight polysulfide from a chlorinated product of 2-mercaptobenzothiazole and polyether dimercaptan and used it as a vulcanization accelerator for diene rubber such as natural rubber. It has been reported (Japanese Patent Application Laid-Open No. 62-100542). In addition, the Koran et al.
-Emulsion polymerization of vinyl pyridine and butadiene to synthesize a high molecular weight polyvinyl pyridine copolymer and reported to be a SBR co-activator (Plast.Rubbe
r Process. Appl. , 12, (2), 81
(1989); Rubber Chem. Techno
l. , 62, (5), 957 (1989)), but has no effect on natural rubber.
【０００７】このように従来より高分子量加硫促進剤に
ついての提案は種々なされているが、広い種類のゴムに
有効で、加硫促進剤等として有効に作用する高分子量の
ゴム配合剤が更に要望されている。As described above, various proposals have been made for a high-molecular-weight vulcanization accelerator, but a high-molecular-weight rubber compounding agent which is effective for a wide variety of rubbers and which effectively acts as a vulcanization accelerator is further proposed. Is requested.
【０００８】本発明は、上記要望に応えたゴム配合剤を
提供することを目的とする。An object of the present invention is to provide a rubber compounding agent that meets the above demands.
【０００９】[0009]
【課題を解決するための手段及び作用】本発明者は、上
記目的を達成すべく鋭意検討を重ねた結果、エポキシ化
天然ゴムとｐ−アミノジフェニルアミンとの反応生成物
がジエン系ゴム及びハロゲン系ゴム双方の加硫促進剤な
どとして有効であることを知見した。Means for Solving the Problems The present inventor has conducted extensive studies to achieve the above object, and as a result, the reaction product of the epoxidized natural rubber and p-aminodiphenylamine is a diene rubber and a halogen type. We have found that it is effective as a vulcanization accelerator for both rubbers.
【００１０】即ち、従来よりエポキシ化天然ゴムは知ら
れているが、本発明者は、このエポキシ化天然ゴムに種
々のアミンを反応させて高分子量の加硫促進剤を合成す
ることを試みた。その結果、エポキシ化天然ゴムとｐ−
アミノジフェニルアミンとの反応によって得られる高分
子量化合物が分子内に水酸基や第二級アミンを有してい
るため、加硫促進剤、老化防止剤、可塑剤などの機能を
兼ね備えた多官能配合剤であり、特に加硫促進剤として
特異的に有効であり、この高分子量化合物をジエン系ゴ
ムやハロゲン系ゴムへ添加したところ、従来の加硫促進
剤と比較して同等の加硫能を有すると共に、加硫物が物
性的にも従来の加硫促進剤と同程度で、耐老化性、可塑
化性、耐ブリード性、分散性に優れ、しかも高分子量で
あるので揮発性が少なく、また加硫時に分解もしないた
め非常に低毒性であることを見い出し、本発明をなすに
至ったものである。That is, although epoxidized natural rubber has been conventionally known, the present inventor tried to synthesize a high molecular weight vulcanization accelerator by reacting various amines with the epoxidized natural rubber. .. As a result, epoxidized natural rubber and p-
Since the high molecular weight compound obtained by the reaction with aminodiphenylamine has a hydroxyl group and a secondary amine in the molecule, it is a multifunctional compounding agent that also has functions such as a vulcanization accelerator, an antioxidant and a plasticizer. Yes, it is specifically effective as a vulcanization accelerator. When this high molecular weight compound is added to a diene rubber or a halogen rubber, it has the same vulcanization ability as conventional vulcanization accelerators. The physical properties of the vulcanizate are similar to those of conventional vulcanization accelerators, and they have excellent aging resistance, plasticization resistance, bleed resistance, and dispersibility. The present invention has been completed by discovering that it has extremely low toxicity because it is not decomposed during sulfurization.
【００１１】従って、本発明は、エポキシ化天然ゴムと
ｐ−アミノジフェニルアミンとの反応生成物からなるゴ
ム配合剤を提供する。Accordingly, the present invention provides a rubber compounding agent comprising a reaction product of an epoxidized natural rubber and p-aminodiphenylamine.
【００１２】以下、本発明について更に詳しく説明する
と、本発明のゴム配合剤は、エポキシ化天然ゴムとｐ−
アミノジフェニルアミンとの反応生成物からなるもので
ある。The present invention will be described in more detail below. The rubber compounding agent of the present invention comprises an epoxidized natural rubber and p-
It is composed of a reaction product with aminodiphenylamine.
【００１３】ここで、エポキシ化天然ゴムは天然ゴムの
不飽和結合をエポキシ化したもので、公知のものを使用
することができる。Here, the epoxidized natural rubber is obtained by epoxidizing the unsaturated bond of natural rubber, and known ones can be used.
【００１４】また、ｐ−アミノジフェニルアミンは下記
式で示されるものである。Further, p-aminodiphenylamine is represented by the following formula.
【００１５】[0015]
【化１】 [Chemical 1]
【００１６】この場合、ｐ−アミノジフェニルアミン以
外の例えばフェニルヒドラジンでは、加硫能が十分では
なく、本発明の目的を達成することができない。In this case, for example, phenylhydrazine other than p-aminodiphenylamine does not have sufficient vulcanizing ability, and the object of the present invention cannot be achieved.
【００１７】上記エポキシ化天然ゴムと芳香族アミンと
の反応は、下記反応式の通りであり、この反応は例えば
Ｊｏｕｒｎａｌ ｏｆ Ａｐｐｌｉｅｄ Ｐｏｌｙｍｅ
ｒＳｃｉｅｎｃｅ， Ｖｏｌ． ３９， ７４９−７５
８（１９９０）に報告されており、このような公知の方
法によって得られたものを使用することができるが、特
にエポキシ化天然ゴムとｐ−アミノジフェニルアミンと
の反応生成物をゴム用配合物に用いる本発明にあって
は、両者をプラストミルなどの粉砕機にベンゼン、メタ
ノールなどの有機溶剤と共に入れ、非酸化性雰囲気で加
熱下に混練する方法で得られたものが好適に用いられ
る。The reaction between the epoxidized natural rubber and the aromatic amine is represented by the following reaction formula. This reaction is, for example, a Journal of Applied Polymer.
rScience, Vol. 39, 749-75
8 (1990), and those obtained by such known methods can be used. In particular, a reaction product of an epoxidized natural rubber and p-aminodiphenylamine is used as a rubber compound. In the present invention to be used, those obtained by a method in which both are put in a crusher such as a plastomill together with an organic solvent such as benzene and methanol and kneaded under heating in a non-oxidizing atmosphere are preferably used.
【００１８】[0018]
【化２】 [Chemical 2]
【００１９】この場合、混練温度、混練時間は、上記反
応を完結させるように選定し得、この際の反応の完結は
エポキシ基の消失の有無をＩＲスペクトル等により追跡
することによって観察することができるが、通常、混練
温度は８０〜２００℃とすることができ、混練時間は３
０分程度で十分である。In this case, the kneading temperature and the kneading time can be selected so as to complete the above reaction, and the completion of the reaction can be observed by tracing the presence or absence of the epoxy group by IR spectrum or the like. However, the kneading temperature can be usually 80 to 200 ° C., and the kneading time is 3
About 0 minutes is sufficient.
【００２０】また、ｐ−アミノジフェニルアミンの使用
量もエポキシ化天然ゴムのエポキシ量に応じて適宜選定
することができるが、通常エポキシ化天然ゴム１００重
量部に対しｐ−アミノジフェニルアミン２０〜５０重量
部とすることができる。The amount of p-aminodiphenylamine used can be appropriately selected according to the epoxy amount of the epoxidized natural rubber, but usually 20 to 50 parts by weight of p-aminodiphenylamine is used per 100 parts by weight of the epoxidized natural rubber. Can be
【００２１】本発明のゴム配合剤は、特に加硫促進剤と
して有効であり、有効なゴムとしては天然ゴム、イソプ
レンゴム（ＩＲ）、スチレンーブタジエンゴム（ＳＢ
Ｒ）、アクリロニトリルーブタジエンゴム（ＮＢＲ）、
ブタジエンゴム（ＢＲ）等のジエン系ゴム、クロロプレ
ンゴム（ＣＲ）、クロロスルホン化ポリエチレン（ＣＳ
Ｍ）、エピクロロヒドリンゴム（ＥＣＯ）、塩素化ポリ
エチレン（ＣＰＥ）などのハロゲン系ゴムが挙げられ
る。The rubber compounding agent of the present invention is particularly effective as a vulcanization accelerator, and effective rubbers include natural rubber, isoprene rubber (IR), and styrene-butadiene rubber (SB).
R), acrylonitrile-butadiene rubber (NBR),
Diene rubbers such as butadiene rubber (BR), chloroprene rubber (CR), chlorosulfonated polyethylene (CS)
M), epichlorohydrin rubber (ECO), chlorinated polyethylene (CPE), and other halogen-based rubbers.
【００２２】本発明のゴム配合剤をこれらのゴムの加硫
促進剤として使用する場合、ゴム成分１００重量部に対
し５〜５０重量部程度の割合で配合することができる。
なお、加硫剤としては、従来使用されている種々のもの
を使用することができるが、本発明の配合剤の高分子量
である利点を生かし、同じく高分子量である不溶性硫黄
が好ましい。また、加硫条件は従来と同様の条件を採用
することができる。When the rubber compounding agent of the present invention is used as a vulcanization accelerator for these rubbers, it can be compounded in an amount of about 5 to 50 parts by weight per 100 parts by weight of the rubber component.
As the vulcanizing agent, various conventionally used vulcanizing agents can be used, but insoluble sulfur having the same high molecular weight is preferable, taking advantage of the high molecular weight of the compounding agent of the present invention. The vulcanization conditions may be the same as the conventional one.
【００２３】[0023]
【実施例】以下、実施例と比較例を示し、本発明を具体
的に説明するが、本発明は下記の実施例に制限されるも
のではない。なお、下記の例において、部は重量部を示
す。EXAMPLES The present invention will be specifically described below by showing Examples and Comparative Examples, but the present invention is not limited to the following Examples. In addition, in the following example, a part shows a weight part.
【００２４】まず、５０％エポキシ化したエポキシ化天
然ゴム（ＥＮＲー５０Ｐ）とｐ−アミノジフェニルアミ
ン（以下、ＡＤＡという）その他のアミンとを東洋精機
製作所製ラボプラストミル５０Ｃー１５０型で混練する
ことにより、表１に示す温度、時間で反応を行い、ＦＴ
ーＩＲ面積比（１２５０ｃｍ-1／１４６０ｃｍ-1）によ
り、エポキシ基の反応減少率を求めた。なお、回転数は
３０ｒｐｍ、ミキサータイプはＲー６０である。結果を
表１に併記する。First, 50% epoxidized epoxidized natural rubber (ENR-50P) and p-aminodiphenylamine (hereinafter referred to as ADA) and other amines are kneaded with a Labo Plastomill 50C-150 type manufactured by Toyo Seiki Seisakusho. The reaction was carried out at the temperature and time shown in Table 1 according to
The reaction reduction rate of the epoxy group was determined from the -IR area ratio (1250 cm -1 / 1460 cm -1 ). The rotation speed is 30 rpm, and the mixer type is R-60. The results are also shown in Table 1.
【００２５】[0025]
【表１】 [Table 1]
【００２６】次に、上記１３０、１６０及び１８０℃の
反応温度で得られた本発明のゴム配合剤（それぞれＥＮ
ＲーＡＤＡ（１３０）、ＥＮＲーＡＤＡ（１６０）及び
ＥＮＲーＡＤＡ（１８０）とする）２０部を、天然ゴム
１００部、酸化亜鉛５部、ステアリン酸２部、カーボン
ブラック（ＨＡＦ）４０部及び不溶性硫黄３部に配合
し、１６０℃でキュラストメータにおける加硫速度を測
定した。図１にその加硫速度を示した。その結果、加硫
速度はＥＮＲー５０ＰとＡＤＡの反応温度により変化す
ることが認められ、１３０℃≫１６０℃≒１８０℃の順
であった。Next, the rubber compounding agent of the present invention obtained at the reaction temperatures of 130, 160 and 180 ° C. (EN respectively)
20 parts of R-ADA (130), ENR-ADA (160) and ENR-ADA (180)), 100 parts of natural rubber, 5 parts of zinc oxide, 2 parts of stearic acid, 40 parts of carbon black (HAF) and It was mixed with 3 parts of insoluble sulfur and the vulcanization rate was measured at 160 ° C. in a curast meter. The vulcanization rate is shown in FIG. As a result, it was recognized that the vulcanization rate changed depending on the reaction temperature of ENR-50P and ADA, and the order was 130 ° C >> 160 ° C≈180 ° C.
【００２７】また、上記加硫物の物性を測定し、従来の
加硫促進剤のＮ−シクロヘキシル−２−ベンゾチアゾリ
ルスルフェンアミド（ＣＺ）配合物の加硫物の物性、及
びＥＮＲー５０Ｐに１４０℃でＣＨ3Ｓ（ＣＨ2）3ＮＨ2
を反応させたＥＮＲーＳーＭｅと比較した。更に、本発
明のＥＮＲーＡＤＡ（１３０）、上記ＣＺ及びＥＮＲー
ＳーＭｅを加硫促進剤として配合した加硫ゴムを７０
℃、９６時間エージングした後の物性の変化を調べ、耐
熱老化性を評価した。これらの結果を表２に併記する。The physical properties of the vulcanizate were measured to determine the physical properties of the vulcanizate of the conventional vulcanization accelerator N-cyclohexyl-2-benzothiazolylsulfenamide (CZ) compound, and ENR-50P. CH 3 S (CH 2 ) 3 NH 2 at 140 ° C
Was compared with the reacted ENR-S-Me. Furthermore, a vulcanized rubber obtained by blending ENR-ADA (130) of the present invention, the above CZ and ENR-S-Me as a vulcanization accelerator is used.
Changes in physical properties after aging at 96 ° C. for 96 hours were examined to evaluate heat aging resistance. The results are also shown in Table 2.
【００２８】更に、図２に示す加硫温度で加硫を行った
場合の引張り強さと加硫温度との関係を同図に示す。Further, the relationship between the tensile strength and the vulcanization temperature when vulcanization is performed at the vulcanization temperature shown in FIG. 2 is shown in the same figure.
【００２９】[0029]
【表２】 [Table 2]
【００３０】表２の結果より、本発明のゴム配合剤は、
従来の加硫促進剤ＣＺに比較して、ムーニー粘度は本発
明品の方が低く、スコーチ性は同程度であった。得られ
た加硫物の物性は近似しているが、本発明品による加硫
ゴムは、非常に大きな伸びを示し、また、加硫温度によ
る物性の変化が非常に小さい配合系であることが認めら
れる。このことから本発明のゴム配合剤は高温度高速度
加硫ができる特徴が認められる。更に、耐熱老化性が非
常に優れていることも認められる。From the results shown in Table 2, the rubber compounding agent of the present invention is
Compared with the conventional vulcanization accelerator CZ, the Mooney viscosity was lower in the product of the present invention, and the scorch property was about the same. Although the physical properties of the obtained vulcanized products are similar, the vulcanized rubber according to the present invention exhibits a very large elongation and is a compounding system in which the change in the physical properties due to the vulcanization temperature is very small. Is recognized. From this, it is recognized that the rubber compounding agent of the present invention is capable of high temperature and high speed vulcanization. Furthermore, it is recognized that the heat aging resistance is very excellent.
【００３１】図２の結果より、ＥＮＲ−ＡＤＡ（１６０
℃）を用いた場合、加硫物の引張強度は加硫温度による
影響が少ないことが認められる。From the result of FIG. 2, ENR-ADA (160
(° C), it is recognized that the tensile strength of the vulcanizate is less affected by the vulcanization temperature.
【００３２】次に、本発明のゴム配合剤（ＥＮＲーＡＤ
Ａ（１６０））を表３に示す配合のクロロプレンゴムに
配合し、加硫状態を測定した。その時の加硫曲線を図３
に示す。更に、得られた加硫ゴムの物性を測定した。結
果を表３に併記する。なお、比較としては、クロロプレ
ンゴムの加硫促進剤として最も多く用いられる２−メル
カプト−２−イミダゾリン（ＥＵ）を使用した。Next, the rubber compound of the present invention (ENR-AD
A (160)) was mixed with the chloroprene rubber having the composition shown in Table 3 and the vulcanized state was measured. Figure 3 shows the vulcanization curve at that time.
Shown in. Furthermore, the physical properties of the obtained vulcanized rubber were measured. The results are also shown in Table 3. For comparison, 2-mercapto-2-imidazoline (EU), which is most often used as a vulcanization accelerator for chloroprene rubber, was used.
【００３３】[0033]
【表３】 [Table 3]
【００３４】表３の結果より、現在使用されている加硫
促進剤とほとんど類似した物性の加硫ゴムが得られ、従
って本発明のゴム配合剤はクロロプレンゴムのようなハ
ロゲン系ゴムの加硫にも有効であることが認められた。From the results shown in Table 3, a vulcanized rubber having almost the same physical properties as the vulcanization accelerator currently used is obtained. Therefore, the rubber compounding agent of the present invention is used for vulcanizing a halogen-based rubber such as chloroprene rubber. Was also found to be effective.
【００３５】[0035]
【発明の効果】以上説明したように、本発明のゴム配合
剤は、ジエン系ゴムやハロゲン系ゴムに配合した場合、
現在使用されている加硫促進剤と同様の加硫能を示すと
共に、得られた加硫ゴムの物性もほぼ同じであり、しか
も高分子量であるので揮発性がなく、また、加硫時に分
解がないなど極めて低毒性であり、これらのことから現
在使用されている有害な加硫促進剤の代替として有効で
ある。As described above, when the rubber compounding agent of the present invention is compounded with a diene rubber or a halogen rubber,
It has the same vulcanization capacity as the vulcanization accelerators currently used, and the physical properties of the vulcanized rubber obtained are almost the same, and since it has a high molecular weight, it is not volatile and decomposes during vulcanization. It has a very low toxicity, such as no chemicals, and is effective as a substitute for the harmful vulcanization accelerators currently used from the above.
【図１】本発明のゴム配合剤を天然ゴムに配合したゴム
組成物の加硫速度を示すグラフである。FIG. 1 is a graph showing the vulcanization rate of a rubber composition in which the rubber compounding agent of the present invention is mixed with natural rubber.
【図２】本発明のゴム配合剤を天然ゴムに配合して得ら
れた加硫物の引張強度と加硫温度との関係を示すグラフ
である。FIG. 2 is a graph showing the relationship between the tensile strength and the vulcanization temperature of the vulcanizate obtained by compounding the natural rubber with the rubber compounding agent of the present invention.
【図３】本発明のゴム配合剤をクロロプレンゴムに配合
したゴム組成物の加硫速度を示すグラフである。FIG. 3 is a graph showing the vulcanization rate of a rubber composition in which the rubber compounding agent of the present invention is mixed with chloroprene rubber.
Claims (1)
ニルアミンとの反応生成物からなるゴム配合剤。1. A rubber compounding agent comprising a reaction product of epoxidized natural rubber and p-aminodiphenylamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9220092A JPH05262920A (en) | 1992-03-18 | 1992-03-18 | Rubber formulating agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9220092A JPH05262920A (en) | 1992-03-18 | 1992-03-18 | Rubber formulating agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05262920A true JPH05262920A (en) | 1993-10-12 |
Family
ID=14047806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9220092A Pending JPH05262920A (en) | 1992-03-18 | 1992-03-18 | Rubber formulating agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05262920A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0946308A1 (en) * | 1996-11-20 | 1999-10-06 | MMR Technologies, Inc. | Liquid ebonite anticorrosive coating for metals |
| EP1479706A1 (en) * | 2003-05-22 | 2004-11-24 | Applied Poleramic, Inc. | Epoxy resin curing agents and epoxy resin compositions |
| JP2012255106A (en) * | 2011-06-09 | 2012-12-27 | Toyo Tire & Rubber Co Ltd | Modified diene-based rubber, rubber composition and pneumatic tire |
-
1992
- 1992-03-18 JP JP9220092A patent/JPH05262920A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0946308A1 (en) * | 1996-11-20 | 1999-10-06 | MMR Technologies, Inc. | Liquid ebonite anticorrosive coating for metals |
| EP0946308A4 (en) * | 1996-11-20 | 2000-12-20 | Mmr Technologies Inc | Liquid ebonite anticorrosive coating for metals |
| EP1479706A1 (en) * | 2003-05-22 | 2004-11-24 | Applied Poleramic, Inc. | Epoxy resin curing agents and epoxy resin compositions |
| JP2012255106A (en) * | 2011-06-09 | 2012-12-27 | Toyo Tire & Rubber Co Ltd | Modified diene-based rubber, rubber composition and pneumatic tire |
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