JPS63291933A - Rubber composition having improved crosslinking efficiency - Google Patents
Rubber composition having improved crosslinking efficiencyInfo
- Publication number
- JPS63291933A JPS63291933A JP12897587A JP12897587A JPS63291933A JP S63291933 A JPS63291933 A JP S63291933A JP 12897587 A JP12897587 A JP 12897587A JP 12897587 A JP12897587 A JP 12897587A JP S63291933 A JPS63291933 A JP S63291933A
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- crosslinking
- weight
- parts
- organic peroxide
- 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 29
- 239000005060 rubber Substances 0.000 title claims abstract description 29
- 239000000203 mixture Substances 0.000 title claims abstract description 8
- 238000004132 cross linking Methods 0.000 title abstract description 28
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 abstract description 8
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 abstract description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract description 3
- 230000007017 scission Effects 0.000 abstract description 2
- NBAUUNCGSMAPFM-UHFFFAOYSA-N 3-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC(C(O)=O)=C1C(O)=O NBAUUNCGSMAPFM-UHFFFAOYSA-N 0.000 abstract 1
- 238000010504 bond cleavage reaction Methods 0.000 abstract 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 abstract 1
- 238000011156 evaluation Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 4
- -1 etc.) Chemical compound 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 229910000071 diazene Inorganic materials 0.000 description 2
- 229920003244 diene elastomer Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- DZCCLNYLUGNUKQ-UHFFFAOYSA-N n-(4-nitrosophenyl)hydroxylamine Chemical compound ONC1=CC=C(N=O)C=C1 DZCCLNYLUGNUKQ-UHFFFAOYSA-N 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 description 1
- CQMIJLIXKMKFQW-UHFFFAOYSA-N 4-phenylbenzene-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C1C1=CC=CC=C1 CQMIJLIXKMKFQW-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- WMVSVUVZSYRWIY-UHFFFAOYSA-N [(4-benzoyloxyiminocyclohexa-2,5-dien-1-ylidene)amino] benzoate Chemical compound C=1C=CC=CC=1C(=O)ON=C(C=C1)C=CC1=NOC(=O)C1=CC=CC=C1 WMVSVUVZSYRWIY-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical class N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、有機過酸化物によるゴムの架橋に際し、架橋
効果を向上させるためにビフェニルテトラカルボキシジ
イミド化合物を加えたゴム組ＩＬ物に関するものである
。Detailed Description of the Invention [Industrial Application Field] The present invention relates to a rubber composite IL product in which a biphenyltetracarboxydiimide compound is added in order to improve the crosslinking effect when crosslinking rubber with an organic peroxide. be.
［従来の技術］
エチレン・プロピレンゴムや多くのジエン系ゴムなどの
架橋方法の一つに有機過酸化物を用いた架橋がある。こ
の有機過酸化物架橋に際して、架橋反応中に発生したラ
ジカルがポリマー鎖を切断するなどの副反応を防ぎ、架
橋効果を向上させる目的で種々の架橋助剤が用いられる
。[Prior Art] One of the crosslinking methods for ethylene propylene rubber and many diene rubbers is crosslinking using an organic peroxide. During this organic peroxide crosslinking, various crosslinking aids are used for the purpose of preventing side reactions such as radicals generated during the crosslinking reaction cutting polymer chains and improving the crosslinking effect.
従来用いられてきた架橋助剤には、！黄の他。The crosslinking aids that have been used in the past include! Besides yellow.
キノンジオキシム系（バラキノンジオキシム、バラ・バ
ラジベンゾイルキノンジオキシムなど）、メタアクリレ
ート系（ラウリルメタアクリレート、メチルメタアクリ
レートなど）、アリル系（ジアリルフタレート、トリア
リルシアヌレートなど）、マレイミド系（マレイミド、
フェニルマレイミドなど）、その他（無水マレイン酸、
ジビニルベンゼンなど）があり、価格、ゴムとの相溶性
、添加剤の種類などを考慮して選択されている。Quinone dioxime types (rose quinone dioxime, rose rose dibenzoylquinone dioxime, etc.), methacrylate types (lauryl methacrylate, methyl methacrylate, etc.), allyl types (diallyl phthalate, triallyl cyanurate, etc.), maleimide types ( maleimide,
phenylmaleimide, etc.), others (maleic anhydride,
divinylbenzene, etc.), and are selected based on factors such as price, compatibility with rubber, and types of additives.
［発明が解決しよう料する問題点コ
しかしながら、この中でアリル系の架橋助剤は一般にメ
タアクリレートと同様に常温で液状であり、配合作業上
やや難がある上、高温では揮発しやすいという難点があ
った。[Problems that the invention aims to solve]However, among these, allyl-based crosslinking aids are generally liquid at room temperature like methacrylates, which poses some difficulties in compounding work, and they also tend to volatilize at high temperatures. was there.
そこで本発明者らは、芳香族ジイミド化合物が高い融点
と耐熱性をもつこと、モノマー架橋助剤の架橋効果は２
官能基のものが最も良いことなどを考慮して鋭意検討し
た結果、下記一般式ＣＩ）および（ｎ）で示されるビフ
ェニルテトラカルボキシジアリルジイミド化合物がゴム
用架橋助剤として有効であることを見出した。Therefore, the present inventors found that the aromatic diimide compound has a high melting point and heat resistance, and that the crosslinking effect of the monomer crosslinking aid is 2.
As a result of intensive studies taking into consideration that those with functional groups are best, it was discovered that biphenyltetracarboxydiallyl diimide compounds represented by the following general formulas CI) and (n) are effective as crosslinking aids for rubber. .
［ただし、一般式ＣＩ）および（ＩＩ）において、Ｒは
アリル（ａｉｌｙｌ ）基を示す、］上記一般式（Ｉ）
および（ｎ）で示される２゜３．３’ 、４’−ビフェ
ニルテトラカルボキシＮ、Ｎ′−ジアリルジイミドおよ
び３．３’ 、４゜４′−ビフェニルテトラカルボキシ
Ｎ、Ｎ’−ジアリルジイミドは、特開昭５６−１１８０
６１号公報に記載されており、適当な架橋剤または硬化
剤によって硬化でき、その硬化物が優れた耐熱性を有す
ることが記載されている。しかし、この化合物が有機過
酸化物によるゴムの架橋に際し、助剤として有効に作用
するかどうかは知られていなかりた。[However, in general formulas CI) and (II), R represents an allyl group] The above general formula (I)
2゜3.3',4'-biphenyltetracarboxyN,N'-diallyldiimide and 3.3',4゜4'-biphenyltetracarboxyN,N'-diallyldiimide represented by (n) are: Japanese Patent Publication No. 56-1180
No. 61 discloses that it can be cured with a suitable crosslinking agent or curing agent, and that the cured product has excellent heat resistance. However, it was not known whether this compound would effectively act as an auxiliary agent when crosslinking rubber with organic peroxides.
本発明は、これらのビフェニルテトラカルボキシジイミ
ド化合物が有効なゴム用架橋助剤であることを見出した
ものである。The present invention is based on the discovery that these biphenyltetracarboxydiimide compounds are effective crosslinking aids for rubber.
［問題点を解決するための手段］
すなわち、本発明は有機過酸化物および前記一般式ＣＩ
）および（ｎ）で示されるビフェニルテトラカルボキシ
ジイミド化合物を含むゴム組成物に関するものである。[Means for Solving the Problems] That is, the present invention provides an organic peroxide and the general formula CI
) and (n).
本発明で用いる有機過酸化物は、ゴム・ラテ・ンクス架
橋用の有機過酸化物であればその種類は特に限定されな
いが、助剤として用いるビフェニルテトラカルボキシジ
イミド化合物が高い融点（２，３，３’ 、４’−ビフ
ェニルテトラカルボキシＮ、Ｎ’−ジアリルジイミドが
１５２．７℃（−次転位）と１７２．５°Ｃ（二次転位
）、３．３’、４．４’−ビフェニルテトラカルボキシ
Ｎ。The type of organic peroxide used in the present invention is not particularly limited as long as it is an organic peroxide for crosslinking rubber, latex, and rubber. 3',4'-biphenyltetracarboxy N,N'-diallyldiimide was heated to 152.7°C (-order rearrangement) and 172.5°C (secondary rearrangement), 3.3',4.4'-biphenyltetra Carboxy N.
Ｎ′−ジアリルジイミドが２３０℃〕をもつので、本発
明は、分解温度が高く、高い温度（１６０℃以上）で架
橋を行なう有機過酸化物を用いる場合に特に有効である
。このような有機過酸化物としては、ｔ−ブチルヒドロ
ベルオキシトやクメンペルオキシドなどのヒドロペルオ
キシド類、ジ−ｔ−ブチルペルオキシドやジクミルペル
オキシドなどのジアルキルペルオキシド類などがある。Since N'-diallyldiimide has a temperature of 230 DEG C., the present invention is particularly effective when using an organic peroxide which has a high decomposition temperature and crosslinks at a high temperature (160 DEG C. or higher). Examples of such organic peroxides include hydroperoxides such as t-butyl hydroperoxide and cumene peroxide, and dialkyl peroxides such as di-t-butyl peroxide and dicumyl peroxide.
また、架橋するゴムとしては、エチレン・プロピレン共
重合系ゴム、ポリブタジェンやポリイソプレンなどのジ
エン系ゴム、ブチルゴム、スチレン・ブタジェン共重合
体やスチレン・イソプレン共重合体などのスチレン共重
合系ゴムのほか、通常有機過酸化物による架橋を行なう
ゴムのすべてを対象とすることができる。Rubbers that can be crosslinked include ethylene/propylene copolymer rubber, diene rubber such as polybutadiene and polyisoprene, butyl rubber, styrene copolymer rubber such as styrene/butadiene copolymer, styrene/isoprene copolymer, etc. , all rubbers that are normally crosslinked with organic peroxides can be targeted.
（Ｉ）式および（ＩＩ）式に示したビフェニルテトラカ
ルボキシジアリルジイミド化合物は、特開昭５６−１１
８０６１号公報に記載された方法によって、２，３．３
’ 、４’−ビフェニルテトラカルボン酸二無水物また
は３．３’ 、４．４’ −ビフェニルテトラカルボン
酸二無水物とアリルアミン（２−プロペニルアミン）と
から合成される。The biphenyltetracarboxydiallyldiimide compounds shown in formulas (I) and (II) are disclosed in Japanese Patent Application Laid-open No. 56-11
2,3.3 by the method described in Publication No. 8061
It is synthesized from ',4'-biphenyltetracarboxylic dianhydride or 3.3',4,4'-biphenyltetracarboxylic dianhydride and allylamine (2-propenylamine).
本発明によれば、このビフェニルテトラカルボキシジイ
ミド化合物を前述の有機過酸化物とともに、通常行なわ
れている混線方法、例えばバンバリーミキサ−等のイン
ターナルミキサー、双腕形ニーダ−、ミキシングロール
などによる混練方法を用い、使用するゴムに適した混練
温度をかけてゴムに混練することにより、架橋効率の高
いゴム組成物を得ることができる。According to the present invention, this biphenyltetracarboxydiimide compound is kneaded with the above-mentioned organic peroxide using a commonly used mixing method, for example, an internal mixer such as a Banbury mixer, a double-arm kneader, a mixing roll, etc. By using this method and kneading into rubber at a kneading temperature suitable for the rubber used, a rubber composition with high crosslinking efficiency can be obtained.
各成分の使用割合は、ゴム１００１量部に対して有機過
酸化物１〜５重量部およびビフェニルテトラカルボン酸
ジアリルジイミド化合物１〜１０重量部が好ましい。The proportions of each component used are preferably 1 to 5 parts by weight of the organic peroxide and 1 to 10 parts by weight of the biphenyltetracarboxylic acid diallyldiimide compound per 1001 parts by weight of the rubber.
上記において、有機過酸化物が１重量部より少ないと十
分な架橋効果が得られず、５重量部を超えると硬化し過
ぎてゴムとしての特性が損なわれる。また、ビフェニル
テトラカルボン酸ジアリルジイミド化合物が１重量部よ
り少ないと助剤としての効果がみられず、１０重量部よ
り多く用いてもその添加効果は上昇しない。In the above, if the amount of organic peroxide is less than 1 part by weight, a sufficient crosslinking effect cannot be obtained, and if it exceeds 5 parts by weight, the rubber properties will be impaired due to excessive curing. Furthermore, if the amount of the biphenyltetracarboxylic acid diallyldiimide compound is less than 1 part by weight, no effect as an auxiliary agent is observed, and even if it is used in an amount greater than 10 parts by weight, the effect of its addition does not increase.
なお、ビフェニルテトラカルボキシジアリルジイミド化
合物は常温では淡桃色の固体であり、混線時にもそのま
までは相溶しないが、高温で架橋反応を行なわせる際に
相溶化する。従って、実際の利用に当っては、微粉状に
してゴム中によく分散させると助剤としての効果が大き
い、混線時に固体であることは、従来の液状タイプのジ
アリル型架橋剤に比べ取扱いが容易であり、混線作業性
゛を改善することになる。Note that the biphenyltetracarboxydiallyl diimide compound is a pale pink solid at room temperature, and is not compatible as it is even when cross-wired, but becomes compatible when a crosslinking reaction is performed at a high temperature. Therefore, in actual use, it is more effective as an auxiliary agent if it is made into a fine powder and well dispersed in the rubber.Since it is a solid during crosslinking, it is difficult to handle compared to the conventional liquid type diallyl type crosslinking agent. This is easy and improves the workability of cross-wire operation.
［実施例］ 以下、本発明を実施例に基きざらに説明する。[Example] Hereinafter, the present invention will be explained in detail based on examples.
（実施例１）
エチレンプロピレンゴム（ＪＳＲＥＰＩＩ、以下ｒＥＰ
ＭＪと略す）１００ｆｆｉ量部に対し、ジクミルペルオ
キシド（以下ｒＤｃＰＪと略す）３重量部および３．３
’ 、４．４’−ビフェニルテトラカルボキシ−Ｎ、Ｎ
’−ジアリルジイミド（以下「ジアリルジイミド」と略
す）１重量部を密閉型混練機で、ｉｏｏ℃、回転数ＳＯ
ｒｐｍにて３分間混練した。混練物の架橋速度をキュラ
ストメータ（ＪＳＲ−ｎ型）にて１７０℃で測定した。(Example 1) Ethylene propylene rubber (JSREPII, hereinafter referred to as rEP)
3 parts by weight of dicumyl peroxide (hereinafter abbreviated as rDcPJ) and 3.3 parts by weight per 100 ffi parts (abbreviated as MJ)
',4.4'-biphenyltetracarboxy-N,N
'-Diallyldiimide (hereinafter abbreviated as "diallyldiimide") 1 part by weight was mixed in a closed kneader at ioo℃ and rotation speed SO.
The mixture was kneaded for 3 minutes at rpm. The crosslinking rate of the kneaded product was measured at 170°C using a Curelastometer (JSR-n type).
その後、混線物をプレスにて１７０℃、５５ｋｇ／ｃｍ
”で加圧成形・架橋し、厚さ１ｍｍのシートを作成した
。得られた架橋シートについて、硬度（Ｊ Ｉ Ｓに６
３０１Ａ型硬度計にて測定）、引張強伸度（１００％伸
張時モジュラスＭ１゜。。After that, the mixed wire was pressed at 170℃ and 55kg/cm.
A sheet with a thickness of 1 mm was created by pressure molding and crosslinking with ``hardness (JIS 6
301A type hardness tester), tensile strength and elongation (modulus M1° at 100% elongation.
２００％伸張時モジュラスＭｆＯ０，３００％伸張時モ
ジュラスＭ３００．破断強度Ｔ！Ｉ、破断時の伸びＥａ
（Ｊ Ｉ ５Ｋ６３０１ダンヘル状３号形状試験片
を用い、室温にて引張速度５０ｍｍ／分で測定）〕およ
び動的弾性率Ｅ’ （オリエンチック社ＤＤＶ−ｒＩ
型レオパイブロンを用いて、室温〜Ｚｏｏ℃、昇温４°
Ｃ／分、振動周波数１１０８゜て測定）を測定した。結
果を表１に示す。Modulus at 200% extension MfO0, Modulus at 300% extension M300. Breaking strength T! I, elongation at break Ea
(measured using a J I 5K6301 Danher shape No. 3 test piece at a tensile speed of 50 mm/min at room temperature)] and dynamic elastic modulus E' (Orientic Co., Ltd. DDV-rI
Using a molded rheopiburon, raise the temperature to 4° from room temperature to Zoo°C.
C/min, vibration frequency 1108°) was measured. The results are shown in Table 1.
（実施例２）
ジアリルジイミド３重量部を用いたほかは、実施例１と
同様に混線、評価を行なった。結果を表１に示す。(Example 2) Crosstalk and evaluation were carried out in the same manner as in Example 1, except that 3 parts by weight of diallyldiimide was used. The results are shown in Table 1.
（実施例３）
ジアリルジイミド５重量部を用いたほかは、実施例１と
同様に混線、評価を行なった。結果を表１に示す。(Example 3) Crosstalk and evaluation were carried out in the same manner as in Example 1, except that 5 parts by weight of diallyldiimide was used. The results are shown in Table 1.
（実施例４）
ＥＰＭ１００重量部に対し、ＤＣＰ５重量部およびジア
リルジイミド３重量部を用い、実施例１と同様に混線、
評価を行なった。結果を表１に示す。(Example 4) Using 5 parts by weight of DCP and 3 parts by weight of diallyldiimide for 100 parts by weight of EPM, crosstalk and
We conducted an evaluation. The results are shown in Table 1.
（実施例５）
ジアリルジイミド５重量部を用いたほかは、実施例４と
同様に混線、評価を行なった。結果を表１に示す。(Example 5) Crosstalk and evaluation were carried out in the same manner as in Example 4, except that 5 parts by weight of diallyldiimide was used. The results are shown in Table 1.
（比較例１）
ＥＰＭ１００重量部に対しＤＣＰ３重量部を用い、実施
例１と同様に混線、評価を行なった。結果を表１に示す
。(Comparative Example 1) Crosstalk and evaluation were conducted in the same manner as in Example 1 using 3 parts by weight of DCP for 100 parts by weight of EPM. The results are shown in Table 1.
（比較例２）
ＤＣＰ５重量部を用いた以外は比較例１と同様に混練、
評価を行なった。結果を表１に示す。(Comparative Example 2) Kneading was carried out in the same manner as in Comparative Example 1 except that 5 parts by weight of DCP was used.
We conducted an evaluation. The results are shown in Table 1.
（比較例３）
ジアリルジイミドの代りにジビニルベンゼン３重量部を
用いた以外は、実施例２と同様に混練、評価を行なった
。結果を表１に示す。(Comparative Example 3) Kneading and evaluation were carried out in the same manner as in Example 2, except that 3 parts by weight of divinylbenzene was used instead of diallyldiimide. The results are shown in Table 1.
（比較例４）
ジアリルジイミドの代りにジビニルベンゼン５重量部を
用いたほかは、実施例５と同様に混練、評価を行なった
。結果を表１に示す。(Comparative Example 4) Kneading and evaluation were carried out in the same manner as in Example 5, except that 5 parts by weight of divinylbenzene was used instead of diallyldiimide. The results are shown in Table 1.
［発明の効果］
以上説明したように、本発明のゴム組成物によれば、ビ
フェニルテトラカルボキシジアリルジイミド化合物を架
橋助剤としてゴムの有機過酸化物架橋に用いることによ
り、ゴム主鎖のラジカル切断を防いでゴムの架橋効率を
上げるばかりでなく、架橋により分子鎖中に耐熱性を示
す分子構造（芳香族環およびイミド環構造）が導入され
るため耐熱性が向上する。更に弾性率、特に高温側での
弾性率が向上する。従って、本発明のゴム組成物は、特
に耐熱性を要求される用途（自動車部品、耐熱ベルト、
電線、タイヤ、ホースなど）において有用である。[Effects of the Invention] As explained above, according to the rubber composition of the present invention, by using the biphenyltetracarboxydiallyldiimide compound as a crosslinking aid for organic peroxide crosslinking of rubber, radical cleavage of the rubber main chain is prevented. This not only increases the crosslinking efficiency of the rubber by preventing this, but also improves heat resistance because crosslinking introduces a heat-resistant molecular structure (aromatic ring and imide ring structure) into the molecular chain. Furthermore, the elastic modulus, especially the elastic modulus on the high temperature side, is improved. Therefore, the rubber composition of the present invention is particularly suitable for applications requiring heat resistance (automobile parts, heat-resistant belts,
useful for electrical wires, tires, hoses, etc.).
Claims (2)
アリル基（ａｌｌｙｌ）基を示す］で示されるビフェニ
ルテトラカルボキシジイミド化合物を含むゴム組成物。(1) Organic peroxides and general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [ I ] or general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [II] [However, general formula [ I ] and [ II], R represents an allyl group.
量部およびビフェニルテトラカルボキシジイミド化合物
１〜１０重量部を含む特許請求の範囲第１項記載のゴム
組成物。(2) The rubber composition according to claim 1, which contains 1 to 5 parts by weight of an organic peroxide and 1 to 10 parts by weight of a biphenyltetracarboxydiimide compound based on 100 parts by weight of rubber.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12897587A JPS63291933A (en) | 1987-05-26 | 1987-05-26 | Rubber composition having improved crosslinking efficiency |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12897587A JPS63291933A (en) | 1987-05-26 | 1987-05-26 | Rubber composition having improved crosslinking efficiency |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63291933A true JPS63291933A (en) | 1988-11-29 |
Family
ID=14998033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12897587A Pending JPS63291933A (en) | 1987-05-26 | 1987-05-26 | Rubber composition having improved crosslinking efficiency |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63291933A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6794455B2 (en) * | 2002-12-12 | 2004-09-21 | Dupont Dow Elastomers | Coagents for fluoroelastomer free radical-curable compositions |
-
1987
- 1987-05-26 JP JP12897587A patent/JPS63291933A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6794455B2 (en) * | 2002-12-12 | 2004-09-21 | Dupont Dow Elastomers | Coagents for fluoroelastomer free radical-curable compositions |
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