JPS63203651A - Novel dinitrodiamine compound - Google Patents
Novel dinitrodiamine compoundInfo
- Publication number
- JPS63203651A JPS63203651A JP3759087A JP3759087A JPS63203651A JP S63203651 A JPS63203651 A JP S63203651A JP 3759087 A JP3759087 A JP 3759087A JP 3759087 A JP3759087 A JP 3759087A JP S63203651 A JPS63203651 A JP S63203651A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- reaction
- formaldehyde
- diaminobutane
- formula
- 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
- 150000001875 compounds Chemical class 0.000 title abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 25
- 239000000654 additive Substances 0.000 abstract description 7
- -1 aliphatic diamine Chemical class 0.000 abstract description 7
- 239000002904 solvent Substances 0.000 abstract description 7
- 230000000996 additive effect Effects 0.000 abstract description 6
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 abstract description 6
- 244000043261 Hevea brasiliensis Species 0.000 abstract description 5
- 229920003052 natural elastomer Polymers 0.000 abstract description 5
- 229920001194 natural rubber Polymers 0.000 abstract description 5
- 239000005700 Putrescine Substances 0.000 abstract description 4
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 3
- 229930040373 Paraformaldehyde Natural products 0.000 abstract description 3
- 229920002866 paraformaldehyde Polymers 0.000 abstract description 3
- 229920003051 synthetic elastomer Polymers 0.000 abstract description 3
- 239000005061 synthetic rubber Substances 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract description 2
- 230000020169 heat generation Effects 0.000 abstract description 2
- 239000003444 phase transfer catalyst Substances 0.000 abstract description 2
- 239000007809 chemical reaction catalyst Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 6
- 239000005060 rubber Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000000605 extraction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000010734 process oil Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 235000014692 zinc oxide Nutrition 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- SUGZATOHBPXTDV-UHFFFAOYSA-N 2-nitrobutane Chemical compound CCC(C)[N+]([O-])=O SUGZATOHBPXTDV-UHFFFAOYSA-N 0.000 description 1
- ZXLQHMOMJDHKJK-UHFFFAOYSA-N 2-nitrooctane Chemical compound CCCCCCC(C)[N+]([O-])=O ZXLQHMOMJDHKJK-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- CJYCVQJRVSAFKB-UHFFFAOYSA-N octadecane-1,18-diamine Chemical compound NCCCCCCCCCCCCCCCCCCN CJYCVQJRVSAFKB-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、一般式ＣＩ）
（式中、凡およびＫは水素原子または炭素数１〜１２の
アルキル基を示し、ｎは４〜１８０整数を示す）
で示されろ新規なジニトロジアミン化合物に関する。Detailed Description of the Invention <Industrial Application Field> The present invention relates to the general formula CI) (wherein and K represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and n is an integer of 4 to 180 ) is a novel dinitrodiamine compound.
〈従来の技術〉
前記一般式（Ｉ）で示されるジニトロジアミン化合物は
本発明者らが初めて見出した新規化合物であって、該化
合物は金剛抽出剤、部用添加剤、ゴム用添加剤等として
、あるいはそれらの中間体として有用であるが、とりわ
け天然ゴムや合成ゴムに対してレジリエンスや耐発熱性
などの動的物性を向上させるための添加剤として極めて
有用である。<Prior Art> The dinitrodiamine compound represented by the above general formula (I) is a new compound discovered for the first time by the present inventors, and the compound is used as a King Kong extractant, an additive for parts, an additive for rubber, etc. or as an intermediate thereof, and is particularly useful as an additive for improving dynamic physical properties such as resilience and heat resistance of natural rubber and synthetic rubber.
従来、前記一般式（Ｉ）で示されるジニトロジアミン化
合物に類似のジニトロジアミン類としては、たとえばＮ
、ｄ＝ビス（２−メチル−２−二トロプロビル）ピ／（
ラシン［Ｊ、 Ａｍ、 Ｃｈｅｍ、 ８ｏｏ、、 ７８
４８２（１９５６）］、Ｎ、Ｎ−ビス（１−ニトロシク
ロヘキシルメチル）−１，２−ジアミノエタン、Ｎ、Ｎ
’−ビス（１−ニトロシクロヘキシルメチル）−１，６
−’） ７ ’ｃ ／ ヘキサン［Ｊ、 Ｏｒｇ、 Ｏ
ｈｅｍ、、 ２８ １１１５（１９５８）］、Ｎ、Ｎ−
ビス（２−ニトロ−２−メチル−ｒ−チル）−１，２−
シフｔ／エタン［ムｕｓｅ、 Ｊ、Ｏｈｅｍ、。Conventionally, as dinitrodiamines similar to the dinitrodiamine compound represented by the general formula (I), for example, N
, d=bis(2-methyl-2-nitroprovir)pi/(
Racine [J, Am, Chem, 8oo,, 78
482 (1956)], N,N-bis(1-nitrocyclohexylmethyl)-1,2-diaminoethane, N,N
'-bis(1-nitrocyclohexylmethyl)-1,6
-') 7'c/Hexane [J, Org, O
hem,, 28 1115 (1958)], N, N-
Bis(2-nitro-2-methyl-r-thyl)-1,2-
Shift/Ethane [Muse, J, Ohem,.
のち金属のキレート化剤等として使用されることが知ら
れている。It is known that it is later used as a metal chelating agent.
〈発明が解決しようとする問題点〉
しかし、このようなジニトロジアミン類がゴムに対して
レジリエンスや耐発熱性などの動的物性を向上させるた
めの添加剤として有用であることは全く、知られていな
い。<Problems to be Solved by the Invention> However, it is not known at all that such dinitrodiamines are useful as additives for improving the dynamic physical properties of rubber such as resilience and heat resistance. Not yet.
一方、本発明者らは上記目的の添加剤を開発すべく極々
検討の結果、新規化合物である前記一般式（１）で示さ
れるジニトロジアミン化合物の開発に成功し、該化合物
が新規用途である上記目的の添加剤として非常に有用で
あり、しかも前述の公知のジニトロジアミン類を同用途
に適用した場合よりも更にすぐれた性能を有することを
見出し、本発明に至った。On the other hand, as a result of extensive studies to develop an additive for the above purpose, the present inventors succeeded in developing a new compound, a dinitrodiamine compound represented by the above general formula (1), and this compound has a new use. It has been found that it is very useful as an additive for the above purpose, and has even better performance than the above-mentioned known dinitrodiamines when applied to the same purpose, leading to the present invention.
く問題点を解決するための手段〉
本発明は、前記一般式α）で示される新規なりニトロジ
アミン但合物を提供するものであり、該化合物は、たと
えば脂肪族ジアミン、ニトロパラフィンおよびホルムア
ルデヒド（もしくはパラホルムアルデヒド）を反応させ
ることにより製造することができる。Means for Solving the Problems> The present invention provides a novel nitrodiamine compound represented by the general formula α), which can be used for example with aliphatic diamines, nitroparaffins, and formaldehyde ( or paraformaldehyde).
ここで、脂肪族ジアミンとしては、たとえば１゜４−ジ
アミノブタン、１，６−ジアミツヘキサン、１．８−ジ
アミノオクタン、１．１０−ジアミノデカン、１，１２
−ジアミノドデカン、１，１８−ジアミノオクタデカン
などが例示され、またニトロパラフィンとしてはニトロ
メタン、ニトロエタン、１−ニトロプロパン、２−ニト
ロプロパン、２−二トロブタン、２−ニトロオクタンな
どが例示される。ホルムアルデヒドとしては通常ホルマ
リンやパラホルムアルデヒドが使用される。Here, as the aliphatic diamine, for example, 1.4-diaminobutane, 1,6-diamithexane, 1.8-diaminooctane, 1.10-diaminodecane, 1,12
-diaminododecane, 1,18-diaminooctadecane, etc., and examples of nitroparaffins include nitromethane, nitroethane, 1-nitropropane, 2-nitropropane, 2-nitrobutane, 2-nitrooctane, etc. Formaldehyde is usually formalin or paraformaldehyde.
反応はこれら脂肪族ジアミン、ニトロパラフィンおよび
ホルムアルデヒドを混合することにより行われるが、こ
れら各原料の仕込みモル比は副生物の生成など反応結果
に大きく影梼するため、一般的には脂肪族ジアミンに対
してホルムアルデヒドは２，２モル倍以下、ニトロパラ
フィンは２モル倍以上であって、かつホルムアルデヒド
より過剰モル使用される。The reaction is carried out by mixing these aliphatic diamines, nitroparaffins, and formaldehyde, but since the molar ratio of each raw material charged greatly affects the reaction results such as the formation of by-products, it is generally On the other hand, formaldehyde is used in a molar amount of 2.2 times or less, and nitroparaffin is used in a molar amount of 2 times or more, in excess of formaldehyde.
この反応１こおいて溶媒は必ずしも必要とせず、無溶媒
下であっても反応は進行するが、必要に応じて低級アル
コール等の溶媒を用いてもよい。In this reaction 1, a solvent is not necessarily required, and the reaction proceeds even in the absence of a solvent, but a solvent such as a lower alcohol may be used if necessary.
また１反応促進のために、触媒として少量のアルカリや
相聞移動触媒を使用してもよい。Further, in order to promote one reaction, a small amount of an alkali or a phase transfer catalyst may be used as a catalyst.
反応温度は通常Ｏ＾１００℃、好ましくは０〜６０℃で
ある。反応終了後、反応混合物をたとえば水および抽出
浴ｔＳ＜たとえばベンゼン、トルエン、キシレン等の炭
化水素）と混合し、抽出処理を行うことにより目的物を
得ることができる。The reaction temperature is usually 0^100°C, preferably 0 to 60°C. After completion of the reaction, the reaction mixture is mixed with, for example, water and an extraction bath tS (eg, hydrocarbon such as benzene, toluene, xylene, etc.), and an extraction treatment is performed to obtain the desired product.
また、必要薔こ応じて前記の抽出処理により得られる抽
出液に酸を加えて結晶を析出させる方法、抽出液をその
まま冷却して再結晶する方法、抽出液から抽出溶媒を蒸
留等により留去させたのら、アルコール類、エステル類
、脂肪族炭化水素等の溶媒を加えて結晶を析出させる方
法などにより精製することができる。In addition, depending on the needs of the extract, there are methods such as adding acid to the extract obtained by the above extraction process to precipitate crystals, cooling the extract as it is and recrystallizing it, and removing the extraction solvent from the extract by distillation etc. After this, it can be purified by adding a solvent such as an alcohol, an ester, or an aliphatic hydrocarbon to precipitate crystals.
〈発明の効果〉
本発明の新規なジニトロジアミン化合物は、天然ゴム、
合成ゴムなどに対するレジリエンスおよび耐発熱性など
の動的物性の向上に非常に有効であり、その工業的利用
価値は高い。<Effects of the Invention> The novel dinitrodiamine compound of the present invention can be applied to natural rubber,
It is very effective in improving dynamic physical properties such as resilience and heat resistance of synthetic rubber, and its industrial value is high.
〈実施例〉 以下、実施例により本発明を説明する。<Example> The present invention will be explained below with reference to Examples.
実施例−１
フラスコに１，４−ジアミノブタン８．８ｆ（０，１モ
ル）、２−ニトロプロパン２１．４ｇ（０，２４モル）
およびメタノール５０１１を仕込み、これぬ８７％ホル
マリン１６．２Ｎ（ホルムアルデヒドとして０．２モル
）を４０〜６０℃で１時間を要して滴下した。その後、
同温度で２時間保温した。Example-1 1,4-diaminobutane 8.8f (0.1 mol) and 2-nitropropane 21.4g (0.24 mol) in a flask
and methanol 5011, and 87% formalin 16.2N (0.2 mol as formaldehyde) was added dropwise at 40 to 60°C over 1 hour. after that,
It was kept at the same temperature for 2 hours.
反応終了後、反応液にトルエン２００ｄを加えて希狙し
、このトルエン層を１％硫酸水溶液１００ｄ、水２００
＋ｗ／で順次洗浄した。After the reaction, 200 d of toluene was added to the reaction solution to dilute it, and the toluene layer was diluted with 100 d of 1% sulfuric acid aqueous solution and 200 d of water.
Washed sequentially with +w/.
トルエン層を減圧下、６０℃以下で濃縮し、溶媒を留去
して淡緑色液状のＮ、Ｎ−ビス（２−二≠
ドロー２−メチルプロピル）−１，１−ジアミノブタン
１８．１Ｆを得た。The toluene layer was concentrated under reduced pressure at 60°C or below, and the solvent was distilled off to obtain pale green liquid N,N-bis(2-2≠draw 2-methylpropyl)-1,1-diaminobutane 18.1F. Obtained.
ｎ” １．４４６５
元素分析値（ＣｔｚＨｚａ”１０４として）ｃ＠
Ｈ（至） Ｎ％
計算値 ４９．６４ ９．０Ｂ １９．８
０実測値 ４９．５２ ８．９８ １９．２
６実施例２〜４
１．４−ジアミノブタンに代えてそれと等モルの表−１
に記載の脂肪族ジアジンをそれぞれ用いる以外は実施例
１と同様に反応、後処理を行い、その後見にｎ−ヘキサ
ンで再結晶してジニトロジアミン化合物を得た。n” 1.4465 Elemental analysis value (as CtzHza”104) c@
H (To) N% Calculated value 49.64 9.0B 19.8
0 Actual value 49.52 8.98 19.2
6 Examples 2 to 4 Table 1 of equimolar amounts in place of 1,4-diaminobutane
The reaction and post-treatment were carried out in the same manner as in Example 1, except that each of the aliphatic diazines described in Example 1 was used, followed by recrystallization from n-hexane to obtain a dinitrodiamine compound.
得られた化合物の融点および元素分析値を表−１に示す
。Table 1 shows the melting point and elemental analysis values of the obtained compound.
参考例１
天然ゴムをベースに下記配合処方に基づきパン←）
バリーミキサーおよびオーブンミルを用いて、ゴム配合
物を作製し、加硫プレスにより、１４５℃、２０分の条
件で加硫し、所定の形状にした後、試験に供した。なお
配合物のうちジニトロジアミン化合物、カーボンブラッ
ク、亜鉛華、プロセスオイル、ステアリン酸については
、第１段目のバンバリーミキサ−で混練配合し、加硫促
進剤、イオウは、第２段目のオーブンミルで４０へ５０
℃の温度にて混線配合した。Reference Example 1 Bread based on the following formulation based on natural rubber ←) A rubber compound was prepared using a Barry mixer and an oven mill, and vulcanized using a vulcanization press at 145°C for 20 minutes to form a specified product. After shaping it into a shape, it was subjected to a test. Of the ingredients, the dinitrodiamine compound, carbon black, zinc white, process oil, and stearic acid are kneaded and blended in the first-stage Banbury mixer, and the vulcanization accelerator and sulfur are mixed in the second-stage oven. Mil to 40 to 50
Cross-mixing was carried out at a temperature of ℃.
（配合処方）
天然ゴム（Ｒ８８謀１） １００重量部
ＨＡＦブラック ４６ステア
リン酸 ８芳香族系プロセ
スオイル ８亜鉛華 ６
加硫促進剤（利） １イ オ
ウ
２ジニトロジアミン化合物
１（＊１）ツクシノールＯＣ２：Ｎ−シクロヘキシル−
２−ベンゾチアゾールスルフェンアミド
（住友化学社品）
（＊）東洋精機製２５０ ｍｌラボブラストミル０を用
いた。オイルバス湿度１７０℃で、各ａｔｇ品及び充填
剤投入後５分間、６Ｑｒｐｍのミキサーの回転数で混練
した。その時のゴム温度は１５０〜１６０℃であった。(Blending prescription) Natural rubber (R88 plot 1) 100 parts by weight HAF black 46 Stearic acid 8 Aromatic process oil 8 Zinc white 6 Vulcanization accelerator 1 Sulfur
2 dinitrodiamine compound
1 (*1) Tsuxinol OC2: N-cyclohexyl-
2-benzothiazolesulfenamide (Sumitomo Chemical Co., Ltd.) (*) 250 ml Labo Blast Mill 0 manufactured by Toyo Seiki was used. The mixture was kneaded at an oil bath humidity of 170°C for 5 minutes after adding each ATG product and filler at a mixer rotation speed of 6 Qrpm. The rubber temperature at that time was 150 to 160°C.
試験結果を表−２に示す。The test results are shown in Table-2.
尚、試験法は次のとおりである。The test method is as follows.
（υ レジリエンス
ＪＩＳ−に−６８０１に準拠し、リエプケタＡ８ＴＭ−
Ｄ−６２３−５８に準拠した。グツドリッチ式の発熱試
験機を用い、荷重８５６ｂ。(υ Based on Resilience JIS-6801, Liepketa A8TM-
Based on D-623-58. Using a Gutdrich type heat generation tester, the load was 856b.
ストローク６．７３５１１１．振動数１８０Ｏｒ、Ｐ、
ｍ−１槽内温度４０℃の条件で、４０分後の発熱温度（
４０分後のゴム温度と初期ゴム温度の差で表示）を測定
した。Stroke 6.735111. Frequency: 180Or, P,
The exothermic temperature (
(expressed as the difference between the rubber temperature after 40 minutes and the initial rubber temperature) was measured.
発熱温度（０が低い程耐発熱性にすぐれることを示す。Exothermic temperature (lower 0 indicates better exothermic resistance.
表−２Table-2
Claims (1)
のアルキル基を示し、ｎは４〜１８の整数を示す） で示される新規なジニトロジアミン化合物[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R and R' are hydrogen atoms or have 1 to 12 carbon atoms.
(n is an integer of 4 to 18)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3759087A JPS63203651A (en) | 1987-02-19 | 1987-02-19 | Novel dinitrodiamine compound |
| EP87110168A EP0253365B1 (en) | 1986-07-16 | 1987-07-14 | Rubber composition |
| DE8787110168T DE3774781D1 (en) | 1986-07-16 | 1987-07-14 | RUBBER BLEND. |
| CA000542109A CA1338446C (en) | 1986-07-16 | 1987-07-15 | Rubber composition |
| US07/496,048 US5106913A (en) | 1986-07-16 | 1990-03-16 | Rubber composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3759087A JPS63203651A (en) | 1987-02-19 | 1987-02-19 | Novel dinitrodiamine compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63203651A true JPS63203651A (en) | 1988-08-23 |
Family
ID=12501757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3759087A Pending JPS63203651A (en) | 1986-07-16 | 1987-02-19 | Novel dinitrodiamine compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63203651A (en) |
-
1987
- 1987-02-19 JP JP3759087A patent/JPS63203651A/en active Pending
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