JPH0582413B2 - - Google Patents
Info
- Publication number
- JPH0582413B2 JPH0582413B2 JP60024380A JP2438085A JPH0582413B2 JP H0582413 B2 JPH0582413 B2 JP H0582413B2 JP 60024380 A JP60024380 A JP 60024380A JP 2438085 A JP2438085 A JP 2438085A JP H0582413 B2 JPH0582413 B2 JP H0582413B2
- Authority
- JP
- Japan
- Prior art keywords
- halogen
- rubber
- containing rubber
- crosslinking
- scorch
- 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.)
- Expired - Lifetime
Links
- 229920001971 elastomer Polymers 0.000 claims description 25
- 239000005060 rubber Substances 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 4
- VZZUPGZLDMTMFL-UHFFFAOYSA-N triazine;trithiole Chemical compound S1SC=CS1.C1=CN=NN=C1 VZZUPGZLDMTMFL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000002787 reinforcement Effects 0.000 claims 1
- 239000000370 acceptor Substances 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 8
- 239000012744 reinforcing agent Substances 0.000 description 7
- 239000012763 reinforcing filler Substances 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000010559 graft polymerization reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- -1 polyethylene Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 229920006027 ternary co-polymer Polymers 0.000 description 2
- RBYFKCAAFQIZAQ-UHFFFAOYSA-N 1h-1,3,5-triazine-2-thione Chemical compound S=C1N=CN=CN1 RBYFKCAAFQIZAQ-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
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- IXDGHAZCSMVIFX-UHFFFAOYSA-N 6-(dibutylamino)-1h-1,3,5-triazine-2,4-dithione Chemical compound CCCCN(CCCC)C1=NC(=S)NC(=S)N1 IXDGHAZCSMVIFX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000005626 carbonium group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920005558 epichlorohydrin rubber Polymers 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CDMIYIVDILNBIJ-UHFFFAOYSA-N triazinane-4,5,6-trithione Chemical compound SC1=NN=NC(S)=C1S CDMIYIVDILNBIJ-UHFFFAOYSA-N 0.000 description 1
- QZQIWEZRSIPYCU-UHFFFAOYSA-N trithiole Chemical compound S1SC=CS1 QZQIWEZRSIPYCU-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
〔産業上の利用分野〕
本発明は、ハロゲン含有ゴム組成物に関する。
更に詳しくは、耐スコーチ性の改善されたハロゲ
ン含有ゴム組成物に関する。
〔従来の技術〕
ハロゲン含有ゴムは、イオウ−受酸剤系の組合
せでも架橋できるが、得られる架橋ゴムの物理的
性質は一般によくなく、そのためチオウレア−受
酸剤系の架橋系が用いられてきた。更に、架橋ゴ
ムの物椎的性質を向上させるために、トリアジン
トリチオール−受酸剤系の組合せも検討されてい
るが、スコーチ性が悪いため実用化できない状態
にある。この架橋系で、トリアジントリチオール
に代えてその誘導体、例えば６−ジブチルアミノ
−１，３，５−トリアジン−２，４−ジチオー
ル、６−ジブチルアミノ−４−ブチルチオ−６−
メルカプト−１，３，５−トリアジンなどを用い
ると、耐スコーチ性は更に悪化する。
〔発明が解決しようとする問題点〕
本発明者は、良好な物理的性質を示す架橋ゴム
を与えるトリアジントリチオール−受酸剤系の耐
スコーチ性を改善し、それに実用性を付与し得る
方法を求めて種々検討の結果、耐スコーチ性の程
度はハロゲン含有ゴム組成物の系中PHに大きく左
右されることをその原因として見出し、その対策
としてPHの調整された補強剤および／または充填
剤を組成物系中に添加することにより、かかる課
題が効果的に解決されることを見出した。
〔問題点を解決するための手段〕および〔作用〕
従つて、本発明は耐スコーチ性の改善されたハ
ロゲン含有ゴム組成物に係り、このハロゲン含有
ゴム組成物は、ハロゲン含有ゴム、架橋剤トリア
ジントリチオールおよび受酸剤を含有する架橋性
組成物中に、ビニル系単量体をグラフト重合する
ことによつてPHを約２〜７の範囲に調整した補強
剤および／または充填剤を添加してなる。
ハロゲン含有ゴムは、架橋点となるハロゲンの
引抜反応を経由してゴムが架橋されるが、トリア
ジントリチオール−受酸剤系を用いた場合にはま
ず架橋点のハロゲンがトリアジントリチオールと
脱ハロゲン化水素化反応し、このときハロゲン含
有ゴム組成物が酸性であればスコーチタイムは長
くなり、逆にアルカリ性であればスコーチタイム
は短かくなる。
このようにゴム組成物のPHによつて左右される
耐スコーチ性は、PH（４％水性けん濁液をPHメー
タにより測定）が約２〜７、好ましくは約３〜６
の範囲に調整された補強剤および／または充填剤
の添加により改善される。かかる補強剤として
は、例えばカーボンブラツク、ホワイトカーボン
などが用いられ、また充填剤としては例えばセラ
イト、タルク、メタけい酸カルシウム、炭酸カル
シウム、グラフアイト、クレーなどが好んで用い
られ、これらはそれぞれ特有の活性基を有し、ゴ
ムとの混合時に相互に反応することが多く、また
独自に異なるPHを有している。
これらの補強剤および／または充填剤のPHの調
整は、そこにビニル単量体、例えばアクリル酸、
メタクリル酸、２−ヒドロキシエチルアクリレー
ト、２−ヒドロキシプロピルアクリレート、２−
ヒドロキシプロピルメタクリレートなどをグラフ
ト重合させることにより行われる。グラフト重合
は、熱、紫外線または放射線などを用いて行わ
れ、放射線が用いられる場合には、例えばCo−
60を約５〜20メガラツド照射すると効率的なグラ
フト率（約５重量％以上、好ましくは約10重量％
以上）でグラフト化される。
補強剤および／または充填剤にグラフト化され
たビニル単量体は、その分子中に含まれるカルボ
キシル基や水酸基がゴム組成物のPHと前記脱ハロ
ゲン化水素化反応の速度をコントロールするもの
と考えられる。
ハロゲン含有ゴムとしては、例えばクロロプレ
ンゴム、エピクロルヒドリンゴム、エピクロルヒ
ドリン−エチレンオキサイド共重合体ゴム、エピ
クロルヒドリン−アリルグリシジルエーテル共重
合体ゴム、エピクロルヒドリン−エチレンオキサ
イド−アリルグリシジルエーテル３元共重合ゴ
ム、エピクロルヒドリン−プロピレンオキサイド
−アリルグリシジルエーテル３元共重合ゴム、ク
ロルスルフオンポリエチレン、塩素化ポリエチレ
ン、塩素化ポリブチル、ハロゲン含有アクリルゴ
ムなどが挙げられる。
また、架橋系の成分としてトリアジントリチオ
ールと組合されて用いられる受酸剤としては、酸
化亜鉛、酸化マグネシウム、酸化鉛、各種のカル
ボニウム塩やヒドロキシ塩、更にはステアリン酸
のアルカリ金属塩なども用いられる。
〔発明の効果〕
本発明に係るハロゲン含有ゴム組成物は、補強
剤および／または充填剤がそれらのPHを調整する
ようにして添加されているため、トリアジントリ
チオール−受酸剤系の架橋系が用いられているに
もかかわらず、耐スコーチ性の顕著な改善が達成
され、架橋物の物理的性質が良好なこととも合ま
つて、そこにすぐれた実用性が得られるようにな
る。
〔実施例〕
次に、実施例について本発明を説明する。
実施例１、比較例１〜２
次の配合割合（重量部）の各配合成分を、12イ
ンチオープンロールを用いて混練し、180℃で５
分間の条件下で架橋を行ない、240×120×２mmの
シート状に成形した。
[Industrial Field of Application] The present invention relates to a halogen-containing rubber composition.
More specifically, the present invention relates to a halogen-containing rubber composition with improved scorch resistance. [Prior Art] Halogen-containing rubbers can be crosslinked using a sulfur-acid acceptor system combination, but the physical properties of the resulting crosslinked rubber are generally poor, and therefore a thiourea-acid acceptor system has been used. Ta. Further, in order to improve the physical properties of cross-linked rubber, a combination of triazine trithiol and acid acceptor system has been studied, but it cannot be put to practical use due to poor scorch properties. In this crosslinking system, triazinetrithiol can be replaced by its derivatives, such as 6-dibutylamino-1,3,5-triazine-2,4-dithiol, 6-dibutylamino-4-butylthio-6-
When mercapto-1,3,5-triazine or the like is used, the scorch resistance is further deteriorated. [Problems to be Solved by the Invention] The present inventor has devised a method for improving the scorch resistance of a triazinetrithiol-acid acceptor system that provides a crosslinked rubber exhibiting good physical properties, and imparting practicality to it. As a result of various studies, we found that the reason for this is that the degree of scorch resistance is greatly affected by the pH in the system of halogen-containing rubber compositions, and as a countermeasure, we developed reinforcing agents and/or fillers with adjusted pH. It has been found that such problems can be effectively solved by adding the above to the composition system. [Means for Solving the Problems] and [Operation] Accordingly, the present invention relates to a halogen-containing rubber composition with improved scorch resistance, and this halogen-containing rubber composition comprises a halogen-containing rubber, a crosslinking agent triazine, A reinforcing agent and/or filler whose pH is adjusted to a range of about 2 to 7 by graft polymerization of a vinyl monomer is added to a crosslinkable composition containing trithiol and an acid acceptor. It becomes. In halogen-containing rubber, the rubber is crosslinked through an abstraction reaction of the halogen, which serves as a crosslinking point, but when a triazine trithiol-acid acceptor system is used, the halogen at the crosslinking point is first dehalogenated with triazine trithiol. A hydrogenation reaction takes place, and if the halogen-containing rubber composition is acidic, the scorch time will be long; on the other hand, if the halogen-containing rubber composition is alkaline, the scorch time will be short. As described above, the scorch resistance depends on the PH of the rubber composition, and the PH (measured with a PH meter of a 4% aqueous suspension) is about 2 to 7, preferably about 3 to 6.
This can be improved by adding reinforcing agents and/or fillers adjusted to a range of . As such reinforcing agents, carbon black, white carbon, etc. are used, and as fillers, for example, celite, talc, calcium metasilicate, calcium carbonate, graphite, clay, etc. are preferably used, and each of these has its own specific characteristics. It has active groups, often reacts with each other when mixed with rubber, and also has its own unique PH. Adjustment of the PH of these reinforcing agents and/or fillers can be achieved by adding vinyl monomers therein, such as acrylic acid,
Methacrylic acid, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-
This is done by graft polymerizing hydroxypropyl methacrylate or the like. Graft polymerization is carried out using heat, ultraviolet rays, radiation, etc. When radiation is used, for example, Co-
When irradiated with about 5 to 20 megarads of 60, an efficient grafting rate (about 5% by weight or more, preferably about 10% by weight) can be achieved.
above). It is believed that the carboxyl and hydroxyl groups contained in the vinyl monomer grafted to the reinforcing agent and/or filler control the PH of the rubber composition and the rate of the dehydrohalogenation reaction. It will be done. Examples of the halogen-containing rubber include chloroprene rubber, epichlorohydrin rubber, epichlorohydrin-ethylene oxide copolymer rubber, epichlorohydrin-allyl glycidyl ether copolymer rubber, epichlorohydrin-ethylene oxide-allyl glycidyl ether ternary copolymer rubber, and epichlorohydrin-propylene oxide. -Allyl glycidyl ether ternary copolymer rubber, chlorsulfon polyethylene, chlorinated polyethylene, chlorinated polybutyl, halogen-containing acrylic rubber, and the like. In addition, as acid acceptors used in combination with triazine trithiol as a component of the crosslinking system, zinc oxide, magnesium oxide, lead oxide, various carbonium salts and hydroxy salts, and even alkali metal salts of stearic acid are used. It will be done. [Effects of the Invention] The halogen-containing rubber composition according to the present invention has reinforcing agents and/or fillers added to adjust their pH, so that the crosslinked triazine trithiol-acid acceptor system Despite the use of scorch resistance, a significant improvement in scorch resistance is achieved, which, combined with the good physical properties of the crosslinked product, gives it excellent practical utility. [Example] Next, the present invention will be explained with reference to an example. Example 1, Comparative Examples 1 to 2 Each of the ingredients in the following proportions (parts by weight) was kneaded using a 12-inch open roll, and
Crosslinking was carried out under conditions of 1 minute, and a sheet of 240 x 120 x 2 mm was formed.
【表】【table】
【表】
実施例２、比較例３〜４
次の配合割合（重量部）の各配分成分を、12イ
ンチオープンロールを用いて混練し、180℃、６
分間−150℃、５時間の条件下で架橋を行ない、
240×120×２mmのシート状に成形した。[Table] Example 2, Comparative Examples 3 to 4 Each component in the following blending ratio (parts by weight) was kneaded using a 12-inch open roll, and heated at 180°C for 60 minutes.
Crosslinking was carried out under the conditions of -150°C for 5 hours,
It was molded into a sheet of 240 x 120 x 2 mm.
【表】
実施例３、比較例５
次の配合割合（重量部）の各配合成分を、12イ
ンチオープンロールを用いて混練し、180℃、６
分間−150℃、15時間の条件下で架橋を行ない、
240×120×２mmのシート状に成形した。[Table] Example 3, Comparative Example 5 The following blending ratios (parts by weight) of each compound were kneaded using a 12-inch open roll, and the mixture was heated at 180°C for 60 minutes.
Crosslinking was carried out under conditions of -150℃ for 15 hours,
It was molded into a sheet of 240 x 120 x 2 mm.
【表】【table】
【表】
以上の各実施例および比較例について、キユラ
ストメーターによる180℃における架橋速度、ス
コーチ計によるスコーチタイムおよびJIS Ｋ−
6301による物理的性質の測定をそれぞれ行なつ
た。得られた結果は、次の表４に示される。[Table] For each of the above Examples and Comparative Examples, the crosslinking rate at 180°C measured by a culastometer, the scorch time measured by a scorch meter, and the JIS K-
The physical properties were measured using 6301. The results obtained are shown in Table 4 below.
Claims (1)
ントリチオールおよび受酸剤を含有する架橋性組
成物中に、ビニル系単量体をグラフト重合するこ
とによつてPHを２〜７の範囲に調整した補強剤お
よび／または充填剤を添加してなる、耐スコーチ
性の改善されたハロゲン含有ゴム組成物。1 Reinforcement in which the pH is adjusted to a range of 2 to 7 by graft polymerizing a vinyl monomer into a crosslinkable composition containing a halogen-containing rubber, triazine trithiol as a crosslinking agent, and an acid acceptor. A halogen-containing rubber composition with improved scorch resistance, which is obtained by adding an agent and/or a filler.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2438085A JPS61185543A (en) | 1985-02-13 | 1985-02-13 | Halogen-containing rubber composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2438085A JPS61185543A (en) | 1985-02-13 | 1985-02-13 | Halogen-containing rubber composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61185543A JPS61185543A (en) | 1986-08-19 |
| JPH0582413B2 true JPH0582413B2 (en) | 1993-11-18 |
Family
ID=12136576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2438085A Granted JPS61185543A (en) | 1985-02-13 | 1985-02-13 | Halogen-containing rubber composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61185543A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH086004B2 (en) * | 1987-03-13 | 1996-01-24 | 日本メクトロン株式会社 | Vulcanizable acrylic rubber compound |
| EP0811659A3 (en) * | 1996-06-06 | 1999-04-28 | Japan Synthetic Rubber Co., Ltd. | Acrylic rubber composition |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5155346A (en) * | 1974-11-11 | 1976-05-15 | Nippon Zeon Co | SUKOOCHIBOSHISEIHORIKUROPURENGOMUSOSEIBUTSU |
| JPS5230287A (en) * | 1975-09-03 | 1977-03-07 | Mitsubishi Chem Ind Ltd | Phosphoric acid-containing carbon black composite |
| JPS5230856A (en) * | 1975-09-03 | 1977-03-08 | Mitsubishi Chem Ind Ltd | Phosphoric acid containing rubber composition |
| JPS58180539A (en) * | 1982-04-19 | 1983-10-22 | Nippon Mektron Ltd | Vulcanizable acrylic rubber blend |
| JPS58222129A (en) * | 1982-06-18 | 1983-12-23 | Nippon Zeon Co Ltd | Method for crosslinking halogen-containing elastomer |
-
1985
- 1985-02-13 JP JP2438085A patent/JPS61185543A/en active Granted
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5155346A (en) * | 1974-11-11 | 1976-05-15 | Nippon Zeon Co | SUKOOCHIBOSHISEIHORIKUROPURENGOMUSOSEIBUTSU |
| JPS5230287A (en) * | 1975-09-03 | 1977-03-07 | Mitsubishi Chem Ind Ltd | Phosphoric acid-containing carbon black composite |
| JPS5230856A (en) * | 1975-09-03 | 1977-03-08 | Mitsubishi Chem Ind Ltd | Phosphoric acid containing rubber composition |
| JPS58180539A (en) * | 1982-04-19 | 1983-10-22 | Nippon Mektron Ltd | Vulcanizable acrylic rubber blend |
| JPS58222129A (en) * | 1982-06-18 | 1983-12-23 | Nippon Zeon Co Ltd | Method for crosslinking halogen-containing elastomer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61185543A (en) | 1986-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |