JPH01306441A - Vulcanizable rubber composition - Google Patents
Vulcanizable rubber compositionInfo
- Publication number
- JPH01306441A JPH01306441A JP63136806A JP13680688A JPH01306441A JP H01306441 A JPH01306441 A JP H01306441A JP 63136806 A JP63136806 A JP 63136806A JP 13680688 A JP13680688 A JP 13680688A JP H01306441 A JPH01306441 A JP H01306441A
- Authority
- JP
- Japan
- Prior art keywords
- pts
- methacrylic acid
- rubber composition
- zinc compound
- parts
- 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 29
- 239000005060 rubber Substances 0.000 title claims abstract description 29
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000003752 zinc compounds Chemical class 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 8
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 8
- 229920001577 copolymer Polymers 0.000 claims abstract description 6
- 239000011362 coarse particle Substances 0.000 claims abstract description 4
- 150000002825 nitriles Chemical class 0.000 claims abstract description 4
- BMFMTNROJASFBW-UHFFFAOYSA-N 2-(furan-2-ylmethylsulfinyl)acetic acid Chemical compound OC(=O)CS(=O)CC1=CC=CO1 BMFMTNROJASFBW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000005641 methacryl group Chemical group 0.000 claims 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract description 6
- -1 etc. Chemical compound 0.000 abstract description 4
- 239000011787 zinc oxide Substances 0.000 abstract description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000012212 insulator Substances 0.000 abstract 1
- 238000004073 vulcanization Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000005973 Carvone Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 150000005678 chain carbonates Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000010060 peroxide vulcanization Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- PIMBTRGLTHJJRV-UHFFFAOYSA-L zinc;2-methylprop-2-enoate Chemical compound [Zn+2].CC(=C)C([O-])=O.CC(=C)C([O-])=O PIMBTRGLTHJJRV-UHFFFAOYSA-L 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（ａ業上の利用）
本発明は加硫性ゴム組成物に関し、さらに詳し力Ｏ晩イ
１ゴ°ム
〈は優れた強度特性を有する≠９症研性組成物に関する
。DETAILED DESCRIPTION OF THE INVENTION (Industrial Use) The present invention relates to a vulcanizable rubber composition, and more specifically, a vulcanizable rubber composition having excellent strength properties. Regarding.
（従来の技術ならびに発明が解決しようとする問題点）
ゴムにジメタクリル酸亜鉛およびまたは塩基性メタアク
リル酸亜鉛を混合して、有機過酸化物で架構するととに
よ９１強度の優れたゴムが得られることは古くから知ら
れている。(Prior Art and Problems to be Solved by the Invention) When zinc dimethacrylate and/or basic zinc methacrylate are mixed with rubber and then framed with an organic peroxide, a rubber with particularly high strength can be obtained. It has been known for a long time that it can be obtained.
すなわち、特開昭５３−１２５１３９は、ポリブタジェ
ンにメタクリル酸、酸化亜鉛、およびｔ−ブチルパーオ
キシベンゾエートを混合して加硫して作られるソリッド
ゴルフボールを開示している。That is, JP-A-53-125139 discloses a solid golf ball made by mixing polybutadiene with methacrylic acid, zinc oxide, and t-butyl peroxybenzoate and vulcanizing the mixture.
特開昭５２−１２１６５３はポリブタジェンとメタアク
リル酸を混合し、次で酸化亜鉛を混合して耐摩耗性に優
れた組成物を得ることを開示している。さらに特開昭５
３−８５８４２はジエン系ゴムとメタアクリル酸、酸化
−４）ｉ；鉛、イｉ機過６♂化物の混合物に、非重合件
カルボンＱを添力１目、？古パ−ツ・例より引張強度に
優れた配合物が得ら、ｉｉろと、とｋ・開示している。JP-A-52-121653 discloses mixing polybutadiene and methacrylic acid, and then mixing zinc oxide to obtain a composition with excellent wear resistance. Furthermore, JP-A-5
3-85842 is a mixture of diene rubber, methacrylic acid, oxidized -4) lead, and mechanical per6-oxide compound, with the addition of non-polymerizable carvone Q. It is disclosed that a compound with superior tensile strength than old parts was obtained.
１、かじ、こわらの加硫ｊ′ムに！Ａｊ戊物り：ｆ、−
の引張′・強さが５００ Ｋ、ｑ／〆以ドでろり１、物
性１ 洒ｊ’？−乃畳、のとは言えない１、
本発明者らはゴムにメタアクリルを俊、亜鉛化ａ物、有
機過酸化物を混合１．ｔパ加硫＋’、、、ｌ ：ｉ Ｊ
、、組が；、物の強度特性についで検δ・ｔＬ、た結果
１、亜鉛化合物か粗大粒子を含まない？二と、アノ・が
適度な極性と１．８テジｔＪル反応性を有することが必
要であ：！〉こｉ！： ’！２＝見い出り、本発明を完
成するに到−、，５Ａ： 。1. For vulcanization of stiff and stiff parts! Aj Bomonori: f, -
The tensile strength is 500 K, the strength is 1, the physical properties are 1, and the strength is 500 K. - It cannot be said that it is a tatami mat. 1. The present inventors mixed methacrylic, zincate, and organic peroxide into rubber. 1. tPa vulcanization+',,,l :i J
,,The result of checking the strength characteristics of the object, δ・tL, is 1.Does it contain zinc compounds or coarse particles? Second, it is necessary that the anno has appropriate polarity and 1.8 tJ reactivity:! 〉Koi! :'! 2=Heading, The present invention has been completed, 5A:.
（問題点を解決するための１″段）
本発明の目的は 、ｌｌ−グレン性不飽和−”、トリル
・−共役ジエン共電１″Ｘ・ゴＩ、に粒径か２０μ以」
−のｍ粒次いでメタクリル酸５！有機過酸化物な混合Ｌ
７て成ることを特徴とする加硫性ゴム組成物を用いると
とにより達成される。(1" step to solve the problem) The purpose of the present invention is to obtain grain size of 20μ or more in grain-unsaturated, tolyl-conjugated diene, and 1"X-goI.
- m grains followed by methacrylic acid 5! Organic peroxide mixture L
This can be achieved by using a vulcanizable rubber composition characterized by comprising:
（構蔗１の詳細／ｌ：パ（＾明）
本発明【”使用Ｊ″５わ６る。１″、グレン性不飽和＝
−） ＩＪルー共役・ジー「、ン共重合ゴムは、アクリ
Ｔ１ニトリル。(Details of structure 1/l: Pa (^ light) The present invention
-) IJ Roux conjugate/G', N copolymer rubber is acrylic T1 nitrile.
メタアクＩＪ ＋＝ 、＝−トリル、、などのエチレン
性不飽和８−トリルノ、１，５・−グクジエン、イソプ
レン６１−一・ペンタジー１じ・などの共役ジエン羊＃
井との共重合１ノ、Ｊ＋ Ｊ、： Ｄ’ ！１．ｆｒＯ
−（ｄ 、Ｊ−記の２種の単量体と共重合［“］゛能７
．ｉ、ｌい、餓体９例えば、ビニル芳香族化合物、（メ
タ）アクリル酸、゛γルヤル（メタ）つ′クリレト、、
フル１キシアルキル（メタ）アクリレ−・−１・、シｙ
“ノｙ”ル４・ル（メタ）アクリ１７〜トなどとの多元
ｊいハ合体２ｔム一ある。ζ、れらのゴムは、エチレン
性不飽２１１−′−トリル竿量体即位を５０・・−６０
重−はチ含有すＸものである。Conjugated dienes such as ethylenically unsaturated 8-tolyl, 1,5-gukudiene, isoprene 61-1, pentadi 1-di, etc.
Copolymerization with I, J+ J,: D'! 1. frO
-(d, J- copolymerization with the two monomers ['']゛ability 7
．． i, l, starvation 9 For example, vinyl aromatic compounds, (meth)acrylic acid,
Full 1-xyalkyl (meth)acrylate -1, cy
There are two types of multi-dimensional combinations with "noy" 4, (meta)acrylic 17, etc. ζ, these rubbers have an ethylenically unsaturated 211-'-tolyl polymerization of 50...-60
Heavy is a substance containing CH.
本発明′？テ使用さノ′１４る酸化形銅、炭酸中鎖など
の亜鉛化合物ｉ、！１１、粗大粒子を除去Ｉ７たもの２
、ノ゛乃・わｊ、風、力分級梼′！等にま−り１．２０
μ以１−のｆ１１粒子夕含改ないＪ：う１／ｉ″！シた
ものが好ましい３．これらの亜鉛化合物の使用板はゴム
１００重量部ＩＣ７’１ ｌ、 １ｎ −・６ＱＭ量部
、好ましくは 〜５Ｏ重盆：部である４１本発明セ使
用されるメタクリル酸量は、ゴム１００重士λ部に対（
１１、〜６０重量部、好ま１． ＜ ＃ま２０〜５０重
量部である。The present invention'? Zinc compounds such as oxidized copper, medium chain carbonate, etc. are used! 11. Remove coarse particles I7 2
, Noeno Waj, Kaze, Power Classification 梼′! Etc. 1.20
It is preferable that the f11 particles of less than 1 μ are not impregnated J: 1/i''! Preferably, the amount of methacrylic acid used in the present invention is ~50 parts λ per 100 parts λ rubber.
11, ~60 parts by weight, preferably 1. <# is 20 to 50 parts by weight.
本発明で使用される亜鉛化合物とメタクリ刀、酸の重量
比は０５／１〜３７′１の範囲で変える。−とができる
。The weight ratio of the zinc compound, methacrylic acid, and acid used in the present invention varies within the range of 05/1 to 37'1. - I can do it.
本発明で使用”されるイ３゛機過酸化物は、通常のゴム
の過酸化物加硫に使用されるものであればよい。The peroxide used in the present invention may be any of those commonly used in the peroxide vulcanization of rubber.
例えばジクミルパ Ｓキザイド、ジーを−・−ブチＡ・
パルオキタイド、を−・プチルクミルバ・−オギザイド
、ベンゾ１ルバー−第４゛サイド、２．５−ジメチル・
〜２．５−ジ（ｔ−プチルバーオＡ−シ）ヘキシン−３
，２，５−ジメチル−２，５−ジ（ベンゾイルパーオキ
シ）へ今リン、２．５−ジメチル−４５−（）（ｔ−７
”ブルバ・寸ギシ）−へ、キサン、偽α′−ビス（ｔ−
７’ブルバ オＡシーｍ −４ノグロビル）ベンビンな
どが挙げらｆｒ、る。これらの有機過酸化物１．１：
１種又は２種以にを使用Ｌ２、通常ゴムｉｏ。For example, Dicumilpa S Kizaid, G...-Buchi A.
Paloxitide, Butylcumylva-Ogizide, Benzol 4th side, 2,5-dimethyl
~2.5-di(t-butylbaoA-di)hexyne-3
, 2,5-dimethyl-2,5-di(benzoylperoxy)hemaphosphorus, 2,5-dimethyl-45-()(t-7
``Bulba-Sugish)-to, Kisan, false α′-bis(t-
7' Bulvao A C m-4 Nogrovir) Benvin, etc. These organic peroxides 1.1:
Use one or more types L2, usually rubber io.
重量部に対して１〕６２〜１０重量部の範囲で使用され
るか、要求さノ１．る物性ｆｆ！［７ｉ′一応じて適宜
最適量を決定することが望捷１．．い◎
本発明の加硫性ジノ１組成物物の製造は仲、鉛化合物の
良好な分散が得らｆｌ、る方法であればいかなる方法に
よっＣもよいが、予め、 ゴムに亜鉛化合物を加え２１
通常ゴム工業で、使用さ）１．る口・−ル、バンバリー
、ニーダ−などＫよりよく混合し１．亜鉛化合物の良好
な分散な得々。後、メタクリル酸を混合または吸収させ
る方法を採用−すＺ）ことが好ち１１、い１、（２かる
後。有機過酸化物を添加し１、均一に混合−すれば本発
明の加硫性ゴム組成物が得ら）する。It is used in the range of 1]62 to 10 parts by weight, or as required. physical properties ff! [7i'] It is desirable to determine the optimal amount accordingly.1. ．． ◎ The vulcanizable Zino-1 composition of the present invention can be manufactured by any method that provides good dispersion of the lead compound. addition 21
Usually used in the rubber industry) 1. 1. Mix better than K, such as a mouthpiece, a Banbury, or a kneader. Good dispersion of zinc compounds. After that, it is preferable to adopt a method of mixing or absorbing methacrylic acid.11.1.(2) After adding the organic peroxide and mixing uniformly, the vulcanization of the present invention can be achieved. A rubber composition is obtained.
本発明の加硫性ゴム組成物において（・ま、他にカー・
ボンブラック、シリカ等の補強剤、炭カル、タルクなど
の充てん剤、 ｌ−リアリルインシアメレ・−ト、ト
リメチロールプロパントリアクリレート。In the vulcanizable rubber composition of the present invention (in addition to car-
Reinforcing agents such as bomb black and silica, fillers such as charcoal and talc, l-realyl inceamelate, and trimethylolpropane triacrylate.
ｍ−フエごレンビスマレイミドなどの架橋助剤、可塑剤
、安定剤、加工助剤６着色剤等の通常ゴム工業で使用さ
れる種々の薬剤を必要（（応ｌ：て適宜混合使用できる
◇
（効果）
かくして本発明Ｖｃ１：れは従来技術に化較ｊ２，７７
、強度特性に優れるゴム加硫物を得ることができる〇従
って本発明の加硫性ゴム組成物はホース類、ロール類、
防振ゴム等の製造に有用である。Requires various chemicals commonly used in the rubber industry, such as crosslinking aids such as m-phegolene bismaleimide, plasticizers, stabilizers, processing aids, and colorants. (Effect) Thus, the present invention Vc1: This is compared to the prior art j2, 77
Therefore, the vulcanizable rubber composition of the present invention can be used for hoses, rolls,
Useful for manufacturing anti-vibration rubber, etc.
（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
。なお、実施例及び比較例中の部及び俤はとくに断りの
ないかぎり重量基準で表示しである。また、混合方法は
ロールによシ表に記載の配合剤を記載項にそれぞれ目視
により充分良好に分散したことを確認しながら順に添加
混合した。これらの混合物を一昼夜熟成して加硫性ゴム
組成物を得た。(Example) The present invention will be described in more detail with reference to Examples below. Note that parts and weights in Examples and Comparative Examples are expressed on a weight basis unless otherwise specified. In addition, the mixing method was as follows: The ingredients listed in the table were sequentially added and mixed using a roll while visually checking that the ingredients were well dispersed. These mixtures were aged for one day to obtain a vulcanizable rubber composition.
実施例１
第１表記載の配合処方により、加硫性ゴム組成物を調整
した。同表記載の加硫条件でプレス加硫して２１ｍ厚さ
の加硫シートを作成し、Ｊ工５Ｋ６３０１に準じて加硫
物性を測定した。得られた結果を第１表に示した。Example 1 A vulcanizable rubber composition was prepared according to the formulation shown in Table 1. A vulcanized sheet with a thickness of 21 m was prepared by press vulcanization under the vulcanization conditions described in the same table, and the vulcanized physical properties were measured according to J-K 5K6301. The results obtained are shown in Table 1.
実施例２
第２表記載（１）配倉処万ＰＣより２、加硫、ケ１、ゴ
、ｆ１君１ハ１？４物る・調整１１．た３、同表記載の
加硫条件でブレ５＜加１ｉ１’ｆｌし、で加硫物ケ斗実
施例１と同様に加硫物４−′□１：、を側νｉ・しｔ゛
、。得られに結ｙ・を第２表・に示ｉ、５た。Example 2 Listed in Table 2 (1) From warehouse PC 2, vulcanization, ke 1, go, f1 1 ha 1?4 material/adjustment 11. 3. Under the vulcanization conditions described in the same table, vulcanize 5 <1i1'fl, and as in Example 1, set the vulcanizate 4-'□1:, on the side νi, . The resulting yields are shown in Table 2.
Claims (1)
合ゴム１００重量部 （ｂ）２０μ以上の粗粒子を５％以下とした亜鉛化合物
１０〜６０重量部 （ｃ）メタクリル酸２０〜６０重量部 （ｄ）有機過酸化物０．２〜１０重量部 を配合してなることを特徴とする加硫性ゴム組成物 ２、メタクリル酸と亜鉛化合物のモル比が１／０．５〜
１／３である請求項１記載の加硫性ゴム組成物 ３、エチレン性不飽和ニトリル−共役ジエン共重合ゴム
に亜鉛化合物を均一に混合した後、メタクリル酸を混合
してメタクリル酸亜鉛を形成させることを特徴とする請
求項１記載の加硫性ゴム組成物[Claims] 1. (a) 100 parts by weight of ethylenically unsaturated nitrile-conjugated diene copolymer rubber (b) 10 to 60 parts by weight of a zinc compound containing 5% or less of coarse particles of 20μ or more (c) Methacryl Vulcanizable rubber composition 2 characterized by blending 20 to 60 parts by weight of acid (d) and 0.2 to 10 parts by weight of organic peroxide, the molar ratio of methacrylic acid and zinc compound being 1/0 .5～
Vulcanizable rubber composition 3 according to claim 1, wherein the zinc compound is uniformly mixed into the ethylenically unsaturated nitrile-conjugated diene copolymer rubber, and then methacrylic acid is mixed to form zinc methacrylate. The vulcanizable rubber composition according to claim 1, characterized in that
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63136806A JPH0819264B2 (en) | 1988-06-03 | 1988-06-03 | Vulcanizable rubber composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63136806A JPH0819264B2 (en) | 1988-06-03 | 1988-06-03 | Vulcanizable rubber composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01306441A true JPH01306441A (en) | 1989-12-11 |
| JPH0819264B2 JPH0819264B2 (en) | 1996-02-28 |
Family
ID=15183947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63136806A Expired - Fee Related JPH0819264B2 (en) | 1988-06-03 | 1988-06-03 | Vulcanizable rubber composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0819264B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994022947A1 (en) * | 1993-03-31 | 1994-10-13 | Nippon Zeon Co., Ltd. | Vulcanizable rubber composition |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49109436A (en) * | 1973-02-20 | 1974-10-17 | ||
| JPS5427553A (en) * | 1977-07-29 | 1979-03-01 | American Cyanamid Co | Production of 22aminoo11 naphthalenesulphonic acid |
| JPS60215085A (en) * | 1984-04-10 | 1985-10-28 | Hayakawa Rubber Co Ltd | Vulcanization type rubber adhesive |
| JPS63136805A (en) * | 1986-11-28 | 1988-06-09 | Sony Corp | Digital gain controller |
| JPS63136804A (en) * | 1986-11-28 | 1988-06-09 | Hitachi Ltd | Ac coupling circuit |
-
1988
- 1988-06-03 JP JP63136806A patent/JPH0819264B2/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49109436A (en) * | 1973-02-20 | 1974-10-17 | ||
| JPS5427553A (en) * | 1977-07-29 | 1979-03-01 | American Cyanamid Co | Production of 22aminoo11 naphthalenesulphonic acid |
| JPS60215085A (en) * | 1984-04-10 | 1985-10-28 | Hayakawa Rubber Co Ltd | Vulcanization type rubber adhesive |
| JPS63136805A (en) * | 1986-11-28 | 1988-06-09 | Sony Corp | Digital gain controller |
| JPS63136804A (en) * | 1986-11-28 | 1988-06-09 | Hitachi Ltd | Ac coupling circuit |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994022947A1 (en) * | 1993-03-31 | 1994-10-13 | Nippon Zeon Co., Ltd. | Vulcanizable rubber composition |
| US5756586A (en) * | 1993-03-31 | 1998-05-26 | Nippon Zeon Co., Ltd. | Vulcanizable rubber composition with unsaturated and metal compounds and organic peroxides |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0819264B2 (en) | 1996-02-28 |
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