JPH1036563A - Rubber composition - Google Patents
Rubber compositionInfo
- Publication number
- JPH1036563A JPH1036563A JP21324196A JP21324196A JPH1036563A JP H1036563 A JPH1036563 A JP H1036563A JP 21324196 A JP21324196 A JP 21324196A JP 21324196 A JP21324196 A JP 21324196A JP H1036563 A JPH1036563 A JP H1036563A
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- acrylonitrile
- compound
- rubber composition
- butadiene rubber
- 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.)
- Granted
Links
- 229920001971 elastomer Polymers 0.000 title claims abstract description 23
- 239000005060 rubber Substances 0.000 title claims abstract description 23
- 229920000459 Nitrile rubber Polymers 0.000 claims abstract description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 12
- 150000001875 compounds Chemical group 0.000 claims abstract description 8
- -1 phosphorus compound Chemical class 0.000 claims abstract description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 4
- 239000011574 phosphorus Substances 0.000 claims abstract description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract 4
- 150000004714 phosphonium salts Chemical group 0.000 claims abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract 2
- 150000003512 tertiary amines Chemical class 0.000 claims abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 abstract description 8
- 239000011593 sulfur Substances 0.000 abstract description 8
- 125000003700 epoxy group Chemical group 0.000 abstract description 7
- 229910017464 nitrogen compound Inorganic materials 0.000 abstract description 4
- 150000002830 nitrogen compounds Chemical class 0.000 abstract description 3
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 abstract 1
- 238000007789 sealing Methods 0.000 abstract 1
- 238000004073 vulcanization Methods 0.000 description 11
- 239000003921 oil Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000010059 sulfur vulcanization Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- DMIDQAQLESZBGF-UHFFFAOYSA-M triethyl(octyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CC)(CC)CC DMIDQAQLESZBGF-UHFFFAOYSA-M 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、アクリロニトリル
−ブタジエンゴム組成物に関する。さらに詳しくは、硫
黄成分を全く含まない加硫可能なアクリロニトリル−ブ
タジエンゴム組成物に関する。TECHNICAL FIELD The present invention relates to an acrylonitrile-butadiene rubber composition. More particularly, it relates to a vulcanizable acrylonitrile-butadiene rubber composition containing no sulfur component.
【０００２】[0002]
【課題を解決しようとする手段】かくして本発明によれ
ば、（ａ）アクリロニトリル−ブタジエンゴム０〜９５
重量部、及び、カルボキシル基を持つアクリロニトリル
−ブタジエンゴム１００〜５重量部からなるゴム１００
重量部に対し、（ｂ）２個以上のエポキシ基を含む化合
物、（ｃ）チッソあるいはリン化合物を配合してなるこ
とを特徴とする加硫可能なゴム組成物が提供される。Thus, according to the present invention, there are provided (a) acrylonitrile-butadiene rubber 0 to 95;
Rubber 100 comprising 100 parts by weight and 100 to 5 parts by weight of an acrylonitrile-butadiene rubber having a carboxyl group
A vulcanizable rubber composition comprising (b) a compound containing two or more epoxy groups and (c) a nitrogen compound or a phosphorus compound with respect to parts by weight is provided.
【０００３】[0003]
【発明が解決しようとする課題】本発明者等は鋭意検討
した結果、カルボキシル基を持つアクリロニトリル−ブ
タジエンゴムをエポキシ化合物で加硫すれば、硫黄成分
を全く含有しない耐油性の優れたゴム組成物となること
を見出し、この知見に基づき本発明を完成するに至っ
た。As a result of intensive studies, the present inventors have found that if an acrylonitrile-butadiene rubber having a carboxyl group is vulcanized with an epoxy compound, a rubber composition containing no sulfur component and having excellent oil resistance can be obtained. And completed the present invention based on this finding.
【０００４】[0004]
【従来の技術】アクリロニトリル−ブタジエンゴムは、
耐熱性、耐油性の優れたゴムであり、その特徴を生かし
オイルシール、Ｏ−リング、パッキン、ガスケットなど
に利用されている。BACKGROUND OF THE INVENTION Acrylonitrile-butadiene rubber is
This rubber is excellent in heat resistance and oil resistance, and is used for oil seals, O-rings, packings, gaskets, etc. by utilizing its characteristics.
【０００５】アクリロニトリル−ブタジエンゴムの加硫
方法としては一般的にはスコーチ時間があり短時間加硫
が可能な硫黄加硫が用いられている。しかし、電子機器
における用途では加硫剤あるいは加硫促進剤中の硫黄化
合物が悪影響を及ぼす場合があり、硫黄成分を全く含ま
ない加硫系が望まれている。硫黄を用いない加硫系とし
て有機過酸化物による加硫があるが、成形性、有機過酸
化物の失効などの問題点がある。[0005] As a method for vulcanizing acrylonitrile-butadiene rubber, sulfur vulcanization which generally has a scorch time and can be vulcanized in a short time is used. However, a sulfur compound in a vulcanizing agent or a vulcanization accelerator may have an adverse effect on use in electronic equipment, and a vulcanization system containing no sulfur component is desired. As a vulcanization system that does not use sulfur, there is vulcanization with an organic peroxide, but there are problems such as moldability and lapse of the organic peroxide.
【０００６】[0006]
【発明の実施の形態】本発明において用いられるアクリ
ロニトリル−ブタジエンゴムはアクリロニトリルとブタ
ジエンの共重合体であり、耐油性の面からアクリロニト
リルは２５％以上が望ましい。DESCRIPTION OF THE PREFERRED EMBODIMENTS The acrylonitrile-butadiene rubber used in the present invention is a copolymer of acrylonitrile and butadiene, and acrylonitrile is desirably 25% or more from the viewpoint of oil resistance.
【０００７】本発明のにおいて用いられるカルボキシル
基を持つアクリロニトリル−ブタジエンゴムはアクリロ
ニトリルとブタジエンとカルボキル基を持つモノマーの
共重合体であり、耐油性の面からアクリロニトリルは２
５％以上が望ましい。カルボキシル基を持つモノマーと
しては、例えば、アクリル酸、メタクリル酸などが挙げ
られる。The acrylonitrile-butadiene rubber having a carboxyl group used in the present invention is a copolymer of acrylonitrile, butadiene, and a monomer having a carboxy group.
5% or more is desirable. Examples of the monomer having a carboxyl group include acrylic acid and methacrylic acid.
【０００８】ゴム１００重量部中カルボキシル基が０．
０１〜０．２モル含有するように、上記アクリロニトリ
ル−ブタジエンゴムとカルボキシル基を持つアクリロニ
トリル−ブタジエンゴムをブレンドする。カルボキシル
基のモル数が上記範囲内であれば、アクリロニトリル−
ブタジエンゴムを必ずしもブレンドしなくてもよい。好
ましくは、ゴム１００重量部に対してカルボキシル基は
０．０２〜０．０８モルである。[0008] Carboxyl groups are included in 100 parts by weight of rubber in an amount of 0.
The acrylonitrile-butadiene rubber and the acrylonitrile-butadiene rubber having a carboxyl group are blended so as to contain from 01 to 0.2 mol. If the number of moles of the carboxyl group is within the above range, acrylonitrile-
Butadiene rubber need not necessarily be blended. Preferably, the carboxyl group is 0.02 to 0.08 mol per 100 parts by weight of rubber.
【０００９】本発明において用いられる（ｂ）２個以上
のエポキシ基を持つ化合物としては、例えば、エチレン
グリコール、プロピレングリコール、ジエチレングリコ
ール、ポリエチレングリコール、ポリプロピレングリコ
ール、トリメチロールプロパン、グリセロールなどの多
官能アルコール類とグリンジルエーテルとの付加物が挙
げられる。また、ビスフェノールＡ型、フェノールノボ
ラック型、ビフェニール型、脂環式型などのエポキシ樹
脂も挙げられる。また、例えば、式１、式２で表わされ
るようなエポキシ変性シリコーンオイルも挙げられる。Examples of the compound (b) having two or more epoxy groups used in the present invention include polyfunctional alcohols such as ethylene glycol, propylene glycol, diethylene glycol, polyethylene glycol, polypropylene glycol, trimethylolpropane and glycerol. And an adduct of glyndyl ether. In addition, epoxy resins such as bisphenol A type, phenol novolak type, biphenyl type and alicyclic type are also included. Further, for example, epoxy-modified silicone oils represented by Formulas 1 and 2 are also included.
【式１】 (Equation 1)
【式２】 (Equation 2)
【００１０】ゴム１００重量部に対してエポキシ基が
０．００５〜０．２モル、好ましくは、０．０１〜０．
８モル含まれるように上記エポキシ化合物を配合する。
本発明において用いられる（ｃ）チッソあるいはリン化
合物は加硫促進剤として用いられる。具体的には、トリ
フェニルフォスフィン、トリフェニルベンジルフォスフ
ォニウムクロライド、テトラブチルフォスフォニウムブ
ロマイドなどのリン化合物、テトラブチルアンモニウム
ブロマイド、ラウリルトリメチルアンモニウムブロマイ
ド、トリエチルオクチルアンモニウムクロライド、トリ
エチレンテトラミン、ｏ−トリルビグアニジンなどの窒
素化合物などが挙げられる。その使用量は、ゴム１００
重量部に対して０．０１ミリモル〜２０ミリモル、好ま
しくは、１ミリモル〜１０ミリモルである。０．０１ミ
リモルより少ない使用量では、加硫が遅く効率的に生産
できない。また、２０ミリモルより多く配合しても更な
る促進効果はない。The epoxy group is present in an amount of 0.005 to 0.2 mol, preferably 0.01 to 0.1 mol, per 100 parts by weight of the rubber.
The above epoxy compound is blended so as to contain 8 mol.
The nitrogen or phosphorus compound (c) used in the present invention is used as a vulcanization accelerator. Specifically, phosphorus compounds such as triphenylphosphine, triphenylbenzylphosphonium chloride, tetrabutylphosphonium bromide, tetrabutylammonium bromide, lauryltrimethylammonium bromide, triethyloctylammonium chloride, triethylenetetramine, o- Nitrogen compounds such as tolylbiguanidine are exemplified. The amount of rubber used is 100
The amount is 0.01 to 20 mmol, preferably 1 to 10 mmol, based on part by weight. If the amount used is less than 0.01 mmol, the vulcanization is too slow to produce efficiently. Further, even if it is added in an amount of more than 20 mmol, there is no further accelerating effect.
【００１１】本発明によって得られるゴム組成物は、通
常ゴムに用いられる配合剤を任意に配合することでき
る。例えば加工性、柔軟性、耐熱性を改良する目的で、
滑剤、加工助剤、可塑剤、老化防止剤を配合することが
できる。また、補強剤、充填剤としてカーボンブラッ
ク、シリカ、クレーなども使用できる。これらは、表面
処理をしていても良い。また、顔料、カップリング剤を
配合することもできる。本発明によって得られるゴム組
成物はアクリロニトリル−ブタジエンゴムのカルボキシ
ル基とエポキシ化合物のエポキシ基が架橋鎖を形成する
ので、通常アクリロニトリル−ブタジエンゴムを加硫す
るときに必要な配合剤、即ち、硫黄、加硫促進剤、加硫
助剤、有機過酸化物、多官能共架橋剤などを必要としな
い。The rubber composition obtained according to the present invention can be arbitrarily compounded with a compounding agent usually used for rubber. For example, to improve workability, flexibility, and heat resistance,
Lubricants, processing aids, plasticizers and anti-aging agents can be included. Further, carbon black, silica, clay and the like can be used as a reinforcing agent and a filler. These may be surface-treated. Further, a pigment and a coupling agent can be blended. Since the rubber composition obtained by the present invention forms a crosslinked chain between the carboxyl group of the acrylonitrile-butadiene rubber and the epoxy group of the epoxy compound, the compounding agent required for vulcanizing the acrylonitrile-butadiene rubber usually includes sulfur, No vulcanization accelerator, vulcanization aid, organic peroxide, polyfunctional co-crosslinking agent, etc. is required.
【００１２】本発明のゴム組成物の調製法は特に限定な
く、前期成分を任意に添加してニーダ、バンバリーミキ
サー、オープンロールなどの通常の混練機によって混合
することができる。このようにして得られる本発明のゴ
ム組成物は、１５０℃〜２００℃の温度で約２分〜３０
分の条件で加硫を行うことができる。また、必要に応じ
て同様の温度で二次加硫を行っても良い。The method for preparing the rubber composition of the present invention is not particularly limited, and the above-mentioned components can be arbitrarily added and mixed with a conventional kneader such as a kneader, a Banbury mixer, or an open roll. The rubber composition of the present invention thus obtained is obtained at a temperature of 150 ° C to 200 ° C for about 2 minutes to 30 minutes.
The vulcanization can be performed under the conditions of minutes. The secondary vulcanization may be performed at the same temperature as needed.
【００１３】[0013]
【実施例】以下に実施例を挙げて本発明をさらに具体的
に説明するが、本発明はかかる実施例に限定されるもの
ではない。なお、部は特に断りのないかぎり重量基準で
ある。 実施例、及び比較例 表１に示した配合処方でポリマー及び配合剤をオープン
ロールにより混合した後、１７０℃で１０分間プレス加
硫を行った。次いでＪＩＳ Ｋー６３０１に準じて各加
硫物の諸物性を測定し、その値を表２に示した。EXAMPLES The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to these examples. Parts are by weight unless otherwise specified. Examples and Comparative Examples After mixing a polymer and a compounding agent by an open roll according to the compounding recipe shown in Table 1, press vulcanization was performed at 170 ° C. for 10 minutes. Next, various physical properties of each vulcanized product were measured according to JIS K-6301, and the values are shown in Table 2.
【００１４】表１ Table 1
【００１５】表２ Table 2
【００１６】[0016]
【発明の効果】かくして本発明により製造された加硫ゴ
ムは良好な耐油性を有するので、この性能を生かし、オ
イルシール、Ｏ−リング、パッキン、ガスケット、など
に使用することができるが、ゴム組成物中に硫黄成分を
全く含まないことから、ゴム中に含まれる硫黄成分が悪
影響を及ぼすような電子機器類のシール、Ｏ−リングな
どに特に有用である。As described above, the vulcanized rubber produced according to the present invention has good oil resistance, and can be used for oil seals, O-rings, packings, gaskets, etc. by utilizing this property. Since the composition does not contain any sulfur component, it is particularly useful for seals, O-rings, and the like of electronic devices in which the sulfur component contained in rubber has an adverse effect.
Claims (3)
０〜９５重量部、及び、カルボキシル基を持つアクリロ
ニトリル−ブタジエンゴム１００〜５重量部からなるゴ
ム１００重量部に対し、（ｂ）２個以上のエポキシ基を
含む化合物、（ｃ）チッソあるいはリン化合物を配合し
てなることを特徴とする加硫可能なゴム組成物。1. An epoxy resin comprising: (a) 0 to 95 parts by weight of an acrylonitrile-butadiene rubber and 100 parts by weight of a rubber comprising 100 to 5 parts by weight of an acrylonitrile-butadiene rubber having a carboxyl group; A vulcanizable rubber composition comprising a compound containing a group and (c) a nitrogen or phosphorus compound.
４級アンモニウム塩である請求項１のゴム組成物。2. The rubber composition according to claim 1, wherein (c) is a tertiary amine or quaternary ammonium salt.
は第４級ホスホニウム塩である請求項１のゴム組成物。3. The rubber composition according to claim 1, wherein (c) is a tertiary phosphine or a quaternary phosphonium salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21324196A JP3416761B2 (en) | 1996-07-23 | 1996-07-23 | Rubber composition for oil seal, O-ring, packing, and gasket |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21324196A JP3416761B2 (en) | 1996-07-23 | 1996-07-23 | Rubber composition for oil seal, O-ring, packing, and gasket |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1036563A true JPH1036563A (en) | 1998-02-10 |
| JP3416761B2 JP3416761B2 (en) | 2003-06-16 |
Family
ID=16635864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21324196A Expired - Fee Related JP3416761B2 (en) | 1996-07-23 | 1996-07-23 | Rubber composition for oil seal, O-ring, packing, and gasket |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3416761B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001014470A1 (en) * | 1999-08-26 | 2001-03-01 | Pirelli Pneumatici S.P.A. | Process for producing tyres, tyres thus obtained and elastomeric compositions used therein |
| JP2006188598A (en) * | 2005-01-06 | 2006-07-20 | Yokohama Rubber Co Ltd:The | Rubber composition |
| WO2015129871A1 (en) * | 2014-02-28 | 2015-09-03 | ミドリ安全株式会社 | Glove and glove composition |
-
1996
- 1996-07-23 JP JP21324196A patent/JP3416761B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001014470A1 (en) * | 1999-08-26 | 2001-03-01 | Pirelli Pneumatici S.P.A. | Process for producing tyres, tyres thus obtained and elastomeric compositions used therein |
| JP2006188598A (en) * | 2005-01-06 | 2006-07-20 | Yokohama Rubber Co Ltd:The | Rubber composition |
| WO2015129871A1 (en) * | 2014-02-28 | 2015-09-03 | ミドリ安全株式会社 | Glove and glove composition |
| US9834665B2 (en) | 2014-02-28 | 2017-12-05 | Kossan Sdn Bhd | Glove and glove composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3416761B2 (en) | 2003-06-16 |
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