JPH0482879A - Phenylenediamine-based compound and rubber composition - Google Patents
Phenylenediamine-based compound and rubber compositionInfo
- Publication number
- JPH0482879A JPH0482879A JP2116431A JP11643190A JPH0482879A JP H0482879 A JPH0482879 A JP H0482879A JP 2116431 A JP2116431 A JP 2116431A JP 11643190 A JP11643190 A JP 11643190A JP H0482879 A JPH0482879 A JP H0482879A
- Authority
- JP
- Japan
- Prior art keywords
- group
- rubber
- general formula
- bis
- iminomethylene
- 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 46
- 239000005060 rubber Substances 0.000 title claims abstract description 46
- 239000000203 mixture Substances 0.000 title claims description 23
- 150000001875 compounds Chemical class 0.000 title abstract description 11
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 title abstract description 3
- -1 p-toluenesulfonyl Chemical group 0.000 claims abstract description 70
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 230000020169 heat generation Effects 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 244000043261 Hevea brasiliensis Species 0.000 claims description 5
- 229920003052 natural elastomer Polymers 0.000 claims description 5
- 229920001194 natural rubber Polymers 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000004986 phenylenediamines Chemical class 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 229920003051 synthetic elastomer Polymers 0.000 claims 2
- 239000005061 synthetic rubber Substances 0.000 claims 2
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 9
- 239000012964 benzotriazole Substances 0.000 abstract description 9
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 abstract description 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 8
- 229920003048 styrene butadiene rubber Polymers 0.000 description 5
- PZBQVZFITSVHAW-UHFFFAOYSA-N 5-chloro-2h-benzotriazole Chemical compound C1=C(Cl)C=CC2=NNN=C21 PZBQVZFITSVHAW-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 2
- SUPSFAUIWDRKKZ-UHFFFAOYSA-N 5-methoxy-2h-benzotriazole Chemical compound C1=C(OC)C=CC2=NNN=C21 SUPSFAUIWDRKKZ-UHFFFAOYSA-N 0.000 description 2
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 2
- MBSXHYDCWYCSME-UHFFFAOYSA-N 5-propan-2-yl-2h-benzotriazole Chemical compound C1=C(C(C)C)C=CC2=NNN=C21 MBSXHYDCWYCSME-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000002832 nitroso derivatives Chemical class 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012763 reinforcing filler Substances 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AXJZCJSXNZZMDU-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanol Chemical compound CC=1N=CNC=1CO AXJZCJSXNZZMDU-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- QWFMNKKZUDBBSE-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1.C1=CNC=N1.C1=CNC=N1 QWFMNKKZUDBBSE-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- GJHVUNPZKRIADK-UHFFFAOYSA-N 2-nitrosoquinoline Chemical class C1=CC=CC2=NC(N=O)=CC=C21 GJHVUNPZKRIADK-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 1
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 1
- HXICLUNGKDYXRL-UHFFFAOYSA-N 4,5-dimethyl-2h-benzotriazole Chemical compound CC1=CC=C2NN=NC2=C1C HXICLUNGKDYXRL-UHFFFAOYSA-N 0.000 description 1
- CWZTZNQOPPLKOK-UHFFFAOYSA-N 4,6-dimethyl-2h-benzotriazole Chemical compound C1=C(C)C=C(C)C2=NNN=C21 CWZTZNQOPPLKOK-UHFFFAOYSA-N 0.000 description 1
- NGKNMHFWZMHABQ-UHFFFAOYSA-N 4-chloro-2h-benzotriazole Chemical compound ClC1=CC=CC2=NNN=C12 NGKNMHFWZMHABQ-UHFFFAOYSA-N 0.000 description 1
- MUIGKBHJQHIEOB-UHFFFAOYSA-N 4-ethoxy-2h-benzotriazole Chemical compound CCOC1=CC=CC2=C1N=NN2 MUIGKBHJQHIEOB-UHFFFAOYSA-N 0.000 description 1
- QRHDSDJIMDCCKE-UHFFFAOYSA-N 4-ethyl-2h-benzotriazole Chemical compound CCC1=CC=CC2=C1N=NN2 QRHDSDJIMDCCKE-UHFFFAOYSA-N 0.000 description 1
- BFBZLCUTOUZMLJ-UHFFFAOYSA-N 4-methoxy-2h-benzotriazole Chemical compound COC1=CC=CC2=NNN=C12 BFBZLCUTOUZMLJ-UHFFFAOYSA-N 0.000 description 1
- ZCFMGIGLXOKMJC-UHFFFAOYSA-N 5-butyl-2h-benzotriazole Chemical compound C1=C(CCCC)C=CC2=NNN=C21 ZCFMGIGLXOKMJC-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- FMGUJLASXUBMOP-UHFFFAOYSA-N N-Methyl-N,4-dinitrosoaniline Chemical compound O=NN(C)C1=CC=C(N=O)C=C1 FMGUJLASXUBMOP-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound 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
- 239000003921 oil Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BGLZVNYGUGILJU-UHFFFAOYSA-N quinolin-8-ylmethanol Chemical compound C1=CN=C2C(CO)=CC=CC2=C1 BGLZVNYGUGILJU-UHFFFAOYSA-N 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920002554 vinyl polymer Chemical group 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- 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、一般式(1)または(II)[式中、R,は
水素原子、アルキル基、ニトロ基のいずれかを表わし、
R2及びR3はそれぞれ独立して水素原子、アルキル基
、フェニル基、ナフチル基、p−トルエンスルホニル基
のいずれかを表わし、R7,はアルキル基、ハロゲン基
、アルコキシ基、アセ1ヘアミド基、ニトロ基、アミノ
基、カルボキシル基から選ばれた一種以上の基を表わし
、TIはO〜4の整数を表わし、R5は、水素原子また
は炭素数18以下のアルキル基、アリル基、炭素数6以
下のシタロアルキル基を表わし、R6及び■り7はそれ
ぞれ独立して水素原子、アルキル基、ヒドロキシアルギ
ル基のいずれかを表わす。コで示されるフェニレンジア
ミン系化合物及びそれを使用してなるゴム組成物に関す
るものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a compound of the general formula (1) or (II) [wherein R represents a hydrogen atom, an alkyl group, or a nitro group,
R2 and R3 each independently represent a hydrogen atom, an alkyl group, a phenyl group, a naphthyl group, or a p-toluenesulfonyl group, and R7 represents an alkyl group, a halogen group, an alkoxy group, an acetylamide group, or a nitro group. , an amino group, and a carboxyl group, TI represents an integer of O to 4, and R5 is a hydrogen atom or an alkyl group having 18 or less carbon atoms, an allyl group, or a cytaloalkyl group having 6 or less carbon atoms. R6 and 7 each independently represent a hydrogen atom, an alkyl group, or a hydroxyargyl group. The present invention relates to a phenylenediamine compound shown in (1) and a rubber composition using the same.
[従来の技術]
省資源、省エネルギーの社会的要求に対応するため、ゴ
ム業界特にタイヤ業界において、ここ数年来、低燃費タ
イヤの開発が盛んに行われるようになってきた。このよ
うな低燃費タイヤの開発には低発熱ゴム組成物が不可欠
であり、例えば、特に米用車用タイヤを目的として、特
開昭57−51503号公報、特開昭57−51504
号公報。[Background Art] In order to meet social demands for resource and energy conservation, the rubber industry, particularly the tire industry, has been actively developing fuel-efficient tires over the past few years. Low heat generation rubber compositions are indispensable for the development of such fuel-efficient tires.
Publication No.
特開昭58−36705号公報に記載されているように
、結合スチレンとビニル結合の含有率をコントロールし
たスチレン−ブタジェンゴムを使用ずと1方法があるが
、これらの方法はスチレン−ブタジェンゴム以外のゴム
、特に重量車両用タイヤに最も広く使用されている天然
ゴムには適用できない。As described in JP-A No. 58-36705, there is one method that does not use styrene-butadiene rubber in which the content of bound styrene and vinyl bonds is controlled, but these methods do not use rubbers other than styrene-butadiene rubber. , especially not applicable to natural rubber, which is most widely used in heavy vehicle tires.
一方、特公昭50−38131号公報、英国特許用1,
185,896号明細書、米国特許用2゜315.85
5号明細書及び米国特許用2,315゜856号明細吉
、米国特許第2,880,240号明細書、米国特許用
3,151,161号明細書。On the other hand, Japanese Patent Publication No. 50-38131, British patent application 1,
No. 185,896, U.S. Patent No. 2°315.85
5 and U.S. Patent No. 2,315°856, U.S. Patent No. 2,880,240, and U.S. Patent No. 3,151,161.
米国特許3,225,100号明細書等によれば、ニト
ロソキノリン類、二l〜ロソアニリン類、例えば、5−
二1−ロソー8−ヒドロキシキノリン。According to US Pat. No. 3,225,100, etc., nitrosoquinolines, di-rosoanilines, e.g.
21-roso-8-hydroxyquinoline.
5−二1ヘロソー8−ヒドロキシメチルキノリン。5-21 Heroso 8-Hydroxymethylquinoline.
p−二1\ロソアニリン、p−二1〜ロッジフェニルア
ミン、N、4−ジニトロソ−N−メチルアニリン、N−
(2−メチル−2−二1〜口プロピル)−4−ニトロソ
アニリン等を添加することにより、ゴムの発熱性が改善
されることが記載されている。p-21\rosoaniline, p-21~Lodgephenylamine, N,4-dinitroso-N-methylaniline, N-
It is described that the heat generating property of rubber is improved by adding (2-methyl-2-2-propyl)-4-nitrosoaniline and the like.
しかしながら、このようなニトロソ化合物は、確かに発
熱性を改善するが、特にポリイソブレンゴl、に適用し
た場合、発熱性を著しく改善するものの、ポリマーのし
やつ解作用が大きく、ゴム組成物の耐摩耗性を著しく低
下させるといった欠点を有している。また、スチレン−
ブタジェン共重合ゴムやポリブタジェンゴム等に二l−
日ソ化合物を適用した場合には、発熱性改良効果は余り
期待でキナイ。また、近年二l−ロソアミンの衛生性が
社会的に問題になったことにより、これらの化合物はい
ずれも使用が困難な状況にある。また、本発明のフェニ
レンジアミン系化合物は、文献に記載のない新規化合物
である。However, although such nitroso compounds do improve the heat generation property, especially when applied to polyisobrene rubber, they have a large softening and decomposition effect on the polymer, and the abrasion resistance of the rubber composition is reduced. It has the disadvantage of significantly reducing performance. Also, styrene
Butadiene copolymer rubber, polybutadiene rubber, etc.
When the Nisso compound is applied, the effect of improving heat generation is not very promising. Furthermore, in recent years, the sanitary properties of dil-rosoamine have become a social problem, making it difficult to use any of these compounds. Furthermore, the phenylenediamine compound of the present invention is a new compound that has not been described in any literature.
[発明が解決しようとする問題点]
本発明は前記のように、従来の発熱改良剤が天然ゴムに
応用することができないこと、ポリイソプレンゴムに適
用した場合、しやつ解作用が大きいこと、更にはスチレ
ン−ブタジェン共重合ゴム・やポリブタジェンゴムに適
用した場合、余り発熱改良効果が期待できないという間
頭を解決するための新規化合物に関する。[Problems to be Solved by the Invention] As mentioned above, the present invention solves the following problems: conventional heat generation improvers cannot be applied to natural rubber, and when applied to polyisoprene rubber, have a large softening and decomposition effect; Furthermore, the present invention relates to a new compound for solving the problem that when applied to styrene-butadiene copolymer rubber and polybutadiene rubber, no significant heat generation improvement effect can be expected.
[問題を解決するための手段]
本発明者らは、上記の欠点を改善することを目的として
、ニトロソ化合物以外の発熱改良剤について鋭意研究し
た結果、本発明に到達したものである。[Means for Solving the Problems] The present inventors have arrived at the present invention as a result of intensive research on heat generation improvers other than nitroso compounds with the aim of improving the above-mentioned drawbacks.
即ち本発明は、上記一般式(1)、(n)で示されシ】
新規フェニレンジアミン系化合物を提供し、かつ、本発
明は、上記一般式(I)、(n)で示される新規フェニ
レンジアミン系化合物を配合してなるゴム組成物を提供
するものである。That is, the present invention has the following general formulas (1) and (n):
The present invention provides a novel phenylenediamine compound, and also provides a rubber composition containing the novel phenylenediamine compound represented by the above general formula (I) or (n).
更にまた、本発明は上記−・般式(1)、(n)で示さ
れる新規フェニレンジアミン系化合物をゴムの発熱改良
剤として配合してなるゴム組成物を提供するものである
。Furthermore, the present invention provides a rubber composition comprising a novel phenylenediamine compound represented by the above general formulas (1) and (n) as a rubber heat generation improver.
本発明のフエニし/ンジアミン系化合物を適用できるゴ
ムとしては、天然ゴム、ポリイソプレンゴム、スヂレン
ーブタジエン共重合ゴム、ポリブタジェンゴム、アクリ
ロニトリル−ブタジェン共重合ゴノ1.エチレン−プロ
プレン−ジエン共重合ゴlz、”(ソブチレンーイソプ
レン共重合ゴム等の単独もしくは、これらの二種または
それ以上を混合したゴム等が挙げられる。Rubbers to which the phenyl diamine compound of the present invention can be applied include natural rubber, polyisoprene rubber, styrene-butadiene copolymer rubber, polybutadiene rubber, and acrylonitrile-butadiene copolymer rubber. Rubbers such as ethylene-propylene-diene copolymer rubber, "sobutylene-isoprene copolymer rubber," or a mixture of two or more of these rubbers may be mentioned.
[作用]
本発明に係る上記一般式(1)、(n)で示されるフェ
ニレンジアミン系化合物は、ベンゾ1〜リアゾール系化
合物またはイミダゾール系化合物とフェニレンジアミン
をメタノール中で混合しておき、これに50〜55℃で
ポル11アルデヒドを反応させることによ−)で容易に
得られる。例えば、ベンゾトリアゾール系化合物として
ベンゾトリアゾール、フェニレンジアミン系化合物とし
てp−フェニレンジアミンを使用したとき、下記のよう
な反応が認められる。[Function] The phenylenediamine compound represented by the above general formulas (1) and (n) according to the present invention can be prepared by mixing a benzo-1-lyazole compound or an imidazole compound and a phenylenediamine in methanol, and then adding the compound to the mixture. It can be easily obtained by reacting pol-11 aldehyde at 50-55°C. For example, when benzotriazole is used as the benzotriazole compound and p-phenylenediamine is used as the phenylenediamine compound, the following reaction is observed.
I
本発明に係るフェニレンジアミン系化合物としては、1
.1’−[p−)ユニしンビス(イミノメチレン)]ビ
ス(ベンゾトリアゾール)、1.1’−[p−フェニレ
ンビス(イミノメチレン)]ビス(4−メチルベンゾト
リアゾール)、1.1’[p−フェニレンビス(イミノ
メチレン)]ビス(5−メチルベンゾトリアゾール)、
1.1’[p−)ユニしンビス(イミノメチレン)]ビ
ス(6−メチルベンゾトリアゾール)、1.1’[p−
)ユニしンビス(−rミノメチレン)コ ビス(7−メ
チルベンゾトリアゾール)、1.1’−[■)−フェニ
レンビス(イミノメチレン)]ビス(4,5−ジメチル
ベンゾトリアゾール)、1.1−[p−)ユニしンビス
(、イミノメチレン)]ビス(4,6−ジメチルベンゾ
トリアゾール)。I As the phenylenediamine compound according to the present invention, 1
.. 1'-[p-)unicinebis(iminomethylene)]bis(benzotriazole), 1.1'-[p-phenylenebis(iminomethylene)]bis(4-methylbenzotriazole), 1.1'[ p-phenylenebis(iminomethylene)]bis(5-methylbenzotriazole),
1.1'[p-)unisinbis(iminomethylene)]bis(6-methylbenzotriazole), 1.1'[p-
) Unishinbis(-rminomethylene)cobis(7-methylbenzotriazole), 1.1'-[■)-phenylenebis(iminomethylene)]bis(4,5-dimethylbenzotriazole), 1.1- [p-)unicinebis(,iminomethylene)]bis(4,6-dimethylbenzotriazole).
1、.1.’−[))−フェニレンビス(イミノメチレ
ン)コビス(4−エチルベンゾトリアゾール)、1゜]
’−4p−フェニレンビス(イミノメチレン)]ビス(
5−イソプロピルベンゾトリアゾール)。1. 1. '-[))-phenylenebis(iminomethylene)cobis(4-ethylbenzotriazole), 1°]
'-4p-phenylenebis(iminomethylene)]bis(
5-isopropylbenzotriazole).
L、1’−[フェニレンビス(イミノメチレン)コビス
(6−イソプロピルベンゾトリアゾール)。L, 1'-[phenylenebis(iminomethylene)cobis(6-isopropylbenzotriazole).
1.1“−[p−)ユニしンビス(イミノメチレン)]
ビス(5−ブチルベンゾトリアゾール)、1゜1°−[
p−フェニレンビス(イミノメチレン)]ビス(4−メ
トキシベンゾトリアゾール)、1゜1’−[p−フェニ
レンビス(イミノメチレン)]ビス(5−メトキシベン
ゾトリアゾール)、1゜]’−[))−フェニレンビス
(イミノメチレン)]ビス(6−メトキシベンゾトリア
ゾール)、1゜1’−[■)−フェニレンビス(イミノ
メチレン)]ビス(4−エトキシベンゾトリアゾールL
1+1、’−[p−フェニレンビ゛ス(イミノメチレン
)]ビス(5−工(−キシベンゾI−リアゾール)、1
゜1°−[p−フェニレンビス(イミノメチレン)]ビ
ス(4−クロルベンゾトリアゾール)、1.1’−[p
−フェニレンビス(イミノメチレン)]ビス(5−クロ
ルベンゾ1−リアゾール)、1.1°−[p−フェニレ
ンビス(イミノメチレン)]ビス(6−クロルベンゾト
リアゾール)、1,1°−[0−フェニレンビス(イミ
ノメチレン)]ビス(ベンツ゛ト・リアゾール)、1.
1“−[m−フェニレンビス(イミノメチレン)]ビス
(ベンゾl−リアゾール)、1.i’−[o−)ユニレ
ンビス(イミノメチレン)]ビス(5−クロルベンゾト
リアゾール)、IJ“−[m−フェニレンビス(イミ、
ノメチレン)]ビス(5−クロルベンゾトリアゾール)
、i、1°−[o−1〜ルイレンビス(イミノメチレン
)]ビス(5−タロルベンゾI−リアゾール) 、 i
、 1 ’ −[m−1ヘルイレンビス(イミノメチレ
ン)]ビス(5−クロルベンゾトリアゾール)、1,1
°−[p−)ユニレンビス(イミノメチレン)]ビス(
〜rミダゾール)、]、1′−[p−フェニレンビス(
イミノメチレン)]ビス(2−メチルイミダゾール)、
i、1“−[p−)ユニレンビス(イミノメチレン)]
ビス(2−エチルイミダゾ−・ル) 、 1.、]−’
−[p−フェニレンビス(イミノメチレン)]ビス(
4−メチル−5−ヒドロキシメチルイミダゾール)、1
.l’−[p−フェニレンビス(イミノメチレン)]ビ
ス(2−エチル4−メチルイミダゾール)yl、1’
[p−)ユニレンビス(イミノメチレン)]ビス(2
−ウンデシルイミダゾール)t 1,1’ [p−フ
エニ1ル
ンビス(イミノメチレン)]ビス(2−ヘプタデシルイ
ミダゾール)yl、1’ [p−フェニレンビス(イ
ミノメチレン)]ビス(2−フェニルイミダゾールLl
、l’ [p−フェニレンビス(イミノメチレン)]
ビス[2−フェニル−4゜5−ジ(ヒドロキシメチル)
イミダゾールコ、1゜1’−[p−フェニレンビス(イ
ミノメチレン)]ビス(2−フェニル−4−メチルイミ
ダゾール)。1.1"-[p-)unishinbis(iminomethylene)]
Bis(5-butylbenzotriazole), 1°1°-[
p-phenylenebis(iminomethylene)]bis(4-methoxybenzotriazole), 1゜1'-[p-phenylenebis(iminomethylene)]bis(5-methoxybenzotriazole), 1゜]'-[)) -phenylenebis(iminomethylene)]bis(6-methoxybenzotriazole), 1゜1'-[■)-phenylenebis(iminomethylene)]bis(4-ethoxybenzotriazole)
1+1,'-[p-phenylenebis(iminomethylene)]bis(5-(-xybenzoI-lyazole), 1
゜1°-[p-phenylenebis(iminomethylene)]bis(4-chlorobenzotriazole), 1.1'-[p
-phenylenebis(iminomethylene)]bis(5-chlorobenzo1-riazole), 1.1°-[p-phenylenebis(iminomethylene)]bis(6-chlorobenzotriazole), 1,1°-[0- Phenylenebis(iminomethylene)]bis(benzenetriazole), 1.
1"-[m-phenylenebis(iminomethylene)]bis(benzo l-lyazole), 1.i'-[o-)unilenebis(iminomethylene)]bis(5-chlorobenzotriazole), IJ"-[m - Phenylene bis (Imi,
bis(5-chlorobenzotriazole)
, i, 1°-[o-1~lylenebis(iminomethylene)]bis(5-thalolbenzo I-riazole), i
, 1'-[m-1 helilenebis(iminomethylene)]bis(5-chlorobenzotriazole), 1,1
°-[p-)unilenebis(iminomethylene)]bis(
~ r midazole),], 1'-[p-phenylenebis(
iminomethylene)]bis(2-methylimidazole),
i, 1″-[p-)unilenebis(iminomethylene)]
Bis(2-ethylimidazole), 1. , ]−'
-[p-phenylenebis(iminomethylene)]bis(
4-methyl-5-hydroxymethylimidazole), 1
.. l'-[p-phenylenebis(iminomethylene)]bis(2-ethyl4-methylimidazole)yl, 1'
[p-)unilenebis(iminomethylene)]bis(2
-undecylimidazole) t 1,1' [p-phenylene bis(iminomethylene)] bis(2-heptadecyl imidazole) yl, 1' [p-phenylene bis(iminomethylene)] bis(2-phenylimidazole Ll
, l' [p-phenylenebis(iminomethylene)]
Bis[2-phenyl-4゜5-di(hydroxymethyl)
imidazole, 1°1'-[p-phenylenebis(iminomethylene)]bis(2-phenyl-4-methylimidazole).
■、1°−[p−フェニレンビス(イミノメチレン)]
ビス(2−フェニル−4−メチル−5−ヒドロキシメチ
ル・rミダゾール)、1.1’−[p−フェニレンビス
(イミノメチレン)]ビス[4,5−ジ(ヒドロキシメ
チル)イミダゾール]、1,1゜−[0−一フエニレン
ビス(イミノメチレン)]ビス(イミダゾール)、1.
i’−[m−フェニレンビス(イミノメチレン)]ビス
(イミダゾール)。■, 1°-[p-phenylenebis(iminomethylene)]
Bis(2-phenyl-4-methyl-5-hydroxymethyl/rmidazole), 1,1'-[p-phenylenebis(iminomethylene)]bis[4,5-di(hydroxymethyl)imidazole], 1, 1°-[0-1phenylenebis(iminomethylene)]bis(imidazole), 1.
i'-[m-phenylenebis(iminomethylene)]bis(imidazole).
1.1°−[0−フェニレンビスC−(ミノメチレン)
]ビス(2−メチルイミダゾール)、1.1’−[rγ
]−フェニレンビス(イミノメチレン)]ビス(2−、
−メチルイミダゾ−・ル) 、 1.1’−[o−1・
ルイレンビス(イミノメチレン)ビス(イミダゾール)
、1.1’−[打)−トルイレンビス(イミノメチレン
)]ビス(イミダゾール)、1.1’−[0−1−ルイ
レンビス(イミノメチレン)]ビス(2−メチルイミダ
ゾール)、1.1’−[m−)ルイレンビス(イミノメ
チレン)]ビス(2−メチルイミダゾール)等が挙げら
れる。1.1°-[0-phenylenebisC-(minomethylene)
]bis(2-methylimidazole), 1.1'-[rγ
]-phenylenebis(iminomethylene)]bis(2-,
-methylimidazole), 1.1'-[o-1.
Luylene bis(iminomethylene) bis(imidazole)
, 1.1'-[d]-toluylenebis(iminomethylene)]bis(imidazole), 1.1'-[0-1-lylenebis(iminomethylene)]bis(2-methylimidazole), 1.1'- Examples include [m-)lylenebis(iminomethylene)]bis(2-methylimidazole).
本発明に係る」二記・・般式(1)、(II)で示され
るフェニレンジアミン系化合物のゴムへの配合にあたっ
ては、単独であっても二種以上併用してもよい。このよ
うなフェニレンジアミン系化合物の配合量は、ゴム10
0重量部に対して0.1〜・10重量部である。0.1
重量部未満ではゴム組成物の発熱改良効果がほとんど期
待できず、10重量部以上多量に添加すると、ゴム組成
物の機能的性質が低下するため好ましくない。According to the present invention, the phenylenediamine compounds represented by formulas (1) and (II) may be incorporated into rubber alone or in combination of two or more. The blending amount of such a phenylenediamine compound is 10% of the rubber.
The amount is 0.1 to 10 parts by weight relative to 0 parts by weight. 0.1
If it is less than 1 part by weight, hardly any effect of improving the heat generation of the rubber composition can be expected, and if it is added in an amount of 10 parts by weight or more, the functional properties of the rubber composition will deteriorate, which is not preferable.
本発明において補強性充填剤(カーボンブラック等)の
配合量は、20〜150重量部であり、2()M置部未
満ではゴム組成物の補強性が劣り、15Q重量部をこえ
ると発熱性改良効果が小さく、また、耐摩耗性等の物性
が著しく劣るなど好ましくない。In the present invention, the blending amount of the reinforcing filler (carbon black, etc.) is 20 to 150 parts by weight, and if it is less than 2()M parts, the reinforcing properties of the rubber composition will be poor, and if it exceeds 15Q parts by weight, it will generate heat. It is undesirable because the improvement effect is small and the physical properties such as wear resistance are significantly inferior.
本発明には対象となるゴム成分に、上記の補強性充填剤
と発熱改良剤以外に、必要に応じて亜鉛華等の金属酸化
物、パラフィン系、ナフテン系または芳香族系の加工油
等の軟化剤、ステアリン酸等の各種高級脂肪酸2着色剤
及び顔料、老化防止剤、紫外線吸収剤、加硫促進剤、加
硫促進助剤。In addition to the above-mentioned reinforcing fillers and heat-generating improvers, the present invention may also contain metal oxides such as zinc white, paraffinic, naphthenic or aromatic processing oils, etc., in the target rubber component. Softeners, various higher fatty acid 2 colorants and pigments such as stearic acid, anti-aging agents, ultraviolet absorbers, vulcanization accelerators, vulcanization accelerators.
加硫剤等の各種配合剤を必要に応じて配合することがで
きる。また、従来から利用されているゴム練り用のオー
ブンロール、バンバリーミキサ−または加注ニー・ダー
等で混合することができる。Various compounding agents such as a vulcanizing agent can be added as necessary. The mixture can also be mixed using conventionally used oven rolls, Banbury mixers, pouring kneaders, etc. for kneading rubber.
本発明のゴl\組成物は、ターrヤ、コンベヤーベルト
、ホース、防振ゴム等のあらゆるゴム製品に適用できる
。The gol composition of the present invention can be applied to all rubber products such as tarpaulins, conveyor belts, hoses, and anti-vibration rubber.
「実施例コ
以下、本発明を合成例、ゴム試験例及び比較例により詳
細に説明するが、本発明はこれらに限定されるものでは
ない。EXAMPLES The present invention will be explained in detail below using synthesis examples, rubber test examples, and comparative examples, but the present invention is not limited thereto.
合成例 1
1.1′−[p−フェニレンビス(イミノメチレン)]
ビス(ベンゾ1へリアゾール)の合成ベンゾトリアゾー
ル35.7g (0,30モル)と1)−フェニレンジ
アミン16.2g (0,15モル)及びメタノール4
00 m lを4ツロコルベンに入れ、撹拌機、還流冷
却器、温度計及び滴下ロー1へを付けて湯浴上にて50
〜55℃に加温撹拌しながら37%ホルムアルデヒド溶
液25.1g(0,31モル)を30分間で加えた。同
温にて4時間撹拌したのち、生成物はる別、洗浄後乾燥
した。生成物1゜1’−[p−フェニレンビス(イミノ
メチレン)]ビス(ベンゾトリアゾール)は52−6
gで収率は94.8%であり、融点は186、一つ−i
、89.0’Cであった。Synthesis example 1 1.1'-[p-phenylenebis(iminomethylene)]
Synthesis of bis(benzo-1-heriazole) 35.7 g (0.30 mol) of benzotriazole, 16.2 g (0.15 mol) of 1)-phenylenediamine and 4 methanol
Pour 0.00 ml into a 4-hour colben, add a stirrer, reflux condenser, thermometer and dropping funnel 1, and boil for 50 ml on a hot water bath.
25.1 g (0.31 mol) of a 37% formaldehyde solution was added over 30 minutes while stirring and heating to ~55°C. After stirring at the same temperature for 4 hours, the product was separated, washed, and dried. The product 1゜1'-[p-phenylenebis(iminomethylene)]bis(benzotriazole) is 52-6
g, yield is 94.8%, melting point is 186, one-i
, 89.0'C.
元素分析
分析値 C:64.61% H:4.94%N:3
0.25%
計算値 (Cユ。I(□8N、3として)C:64.8
5% B−I:4.90%N:30.25%
IR(KB r)am−’
3325.1518,1280,1155゜818、
745
合成例 2
1.1’−[p−)ユニレンビス(イミノメチレン)]
ビス(イミダゾール)の合成
イミダゾール20.4g (0,30モル)とp−フ二
ユニンジアミン16.2g (0,15モル)及びメタ
ノール200m1を4ツロコルベンに入れ、撹拌機、還
流冷却B1÷、温度計及び滴下ロー1・を付けて湯浴上
にて50〜55℃に加温撹拌しながら37%ホル11ア
ルデヒド溶液25.1g (0,31モル)を30分間
で加えた。同温にて4時間撹拌したのち、減圧にて溶媒
を留去しメ、タノールにて再結晶した。生成物1.1°
−[p−フェニレンビス(、イミノメチレン)]ビス(
イミダゾール)は36 、5 gで収率は90.8%で
あり、融点は94゜2、−97.6’Cであった。Elemental analysis analysis value C: 64.61% H: 4.94% N: 3
0.25% Calculated value (Cyu.I (□8N, 3)C:64.8
5% B-I: 4.90% N: 30.25% IR (KB r) am-' 3325.1518, 1280, 1155°818,
745 Synthesis Example 2 1.1'-[p-)unilenebis(iminomethylene)]
Synthesis of bis(imidazole) 20.4 g (0.30 mol) of imidazole, 16.2 g (0.15 mol) of p-furniunindiamine, and 200 ml of methanol were placed in a 4-liter colben, stirred with a stirrer, reflux cooling B1 ÷, and a thermometer. Then, 25.1 g (0.31 mol) of a 37% formaldehyde solution was added over 30 minutes while stirring and heating the mixture to 50 to 55° C. on a water bath with a dropping funnel attached. After stirring at the same temperature for 4 hours, the solvent was distilled off under reduced pressure and the mixture was recrystallized from ethanol. Product 1.1°
-[p-phenylenebis(, iminomethylene)]bis(
(imidazole) was 36.5 g, yield was 90.8%, and the melting point was 94°2, -97.6'C.
G
元素分析
分析値 C:62.49% H:6.08%N:
31.23%
計算値 (C□4H,C,N6として)C:62.67
% J−1:6.01%N:31.32%
I I)−(Kr3 r) crn−’1510.12
65,1210,1060゜8]−5
合成例 3
1.1′−[m−フェニレンビス(イミノメチレン)]
ビス(ベンゾI・リアゾール)の合成ベンゾトリアゾー
ル11.9g (0,1モル)。G Elemental analysis analysis value C: 62.49% H: 6.08% N:
31.23% Calculated value (as C□4H,C,N6)C:62.67
% J-1: 6.01% N: 31.32% I I)-(Kr3 r) crn-'1510.12
65,1210,1060°8]-5 Synthesis Example 3 1.1'-[m-phenylenebis(iminomethylene)]
Synthesis of bis(benzo I lyazole) 11.9 g (0.1 mol) of benzotriazole.
1)1−フェニレンジアミン5−4g (0,05モル
)。1) 5-4 g (0.05 mol) of 1-phenylenediamine.
メタノール200m1及び37%ホルマリン溶液81−
g(0,1モル)を用いて、合成例 1と同様に合成し
た。生成物1.i’−[rn−)ユニレンビス(、イミ
ノメチレン)コビス(ベンゾトリアゾール)は、14.
7gで収率は84.0%であり、融点は24.9 、0
〜252.6℃であった。200ml methanol and 81% 37% formalin solution
Synthesis was carried out in the same manner as in Synthesis Example 1 using g (0.1 mol). Product 1. i'-[rn-)unilenebis(,iminomethylene)cobis(benzotriazole) is 14.
Yield is 84.0% at 7g, melting point is 24.9,0
The temperature was ~252.6°C.
元素分析
分析値 C:64.4.6% H:4.94%N:
30.13%
計算値 (C20Ht e N eとして)C:64.
85% I−I:4.90%N:30.25%
合成例 4
1.1’−[m−トルイレンビス(イミノメチレン)]
ビス(イミダゾール)の合成
イミダゾール6.8g (0,1モル)、m−トルイレ
ンジアミン6.1g (0,05モル)、メタノール2
00 m l及び37%ホルマリン溶液8.1g(0,
1モル)を用いて合成例 1と同様に合成した。生成物
1.1’−[m−トルイレンビス(イミノメチレン)]
ビス(イミダゾール)は11.4gで収率は80.8%
であり、融点は210.6〜213.2°Cであった。Elemental analysis analysis values C: 64.4.6% H: 4.94% N:
30.13% Calculated value (as C20Ht e Ne) C: 64.
85% I-I: 4.90% N: 30.25% Synthesis Example 4 1.1'-[m-toluylenebis(iminomethylene)]
Synthesis of bis(imidazole) Imidazole 6.8 g (0.1 mol), m-tolylenediamine 6.1 g (0.05 mol), methanol 2
00 ml and 8.1 g of 37% formalin solution (0,
1 mol) in the same manner as in Synthesis Example 1. Product 1.1'-[m-toluylenebis(iminomethylene)]
Bis(imidazole) is 11.4g and yield is 80.8%
The melting point was 210.6-213.2°C.
元素分析
分析値 C:63.45% H:6.52%N:2
9.95%
計算値 (CxsHtoNcとして)
C二 63.81 % ■(二 6.43%N:
29.76%
ゴム試験例
第1表に示した配合処方に従って、常法により混合し、
ゴム組成物を得た。配合ゴムを145℃で30分間プレ
ス加硫後、得られた加硫試料についてJ I’S K
6301 (加硫ゴム物理試験方法)に準拠して反発弾
性試験を行った。更にASTM−L’)−623−58
に準拠して耐発熱性試験をグツドリッチ式の発熱試験機
を用いて行い、荷重35■1)、ストローク6.35m
m、振動数1800r、p、rr+、、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。それらの結果を
第2表に示した。Elemental analysis analysis value C: 63.45% H: 6.52% N: 2
9.95% Calculated value (as CxsHtoNc) C2 63.81% ■(2 6.43%N:
29.76% Rubber Test Example Mix according to the formulation shown in Table 1 in a conventional manner,
A rubber composition was obtained. After press vulcanizing the compounded rubber at 145°C for 30 minutes, J I'S K
A rebound resilience test was conducted in accordance with 6301 (Physical Test Methods for Vulcanized Rubber). Furthermore, ASTM-L')-623-58
A heat resistance test was conducted using a Gutdrich heat generation tester in accordance with
m, frequency 1800r, p, rr+, temperature inside the tank 40℃
Under these conditions, the exothermic temperature after 40 minutes (expressed as the difference between the rubber temperature after 40 minutes and the initial rubber temperature) was measured. The results are shown in Table 2.
(以下余白)
[発明の効果コ
以上のことから明らかなように、本発明に係る新規フェ
ニレンジアミン系化合物は、ゴムの発熱改良剤として有
用であり、これを配合してなるゴム組成物は、発熱改良
効果が著しいことがわかる。(Left below) [Effects of the Invention] As is clear from the above, the novel phenylenediamine compound according to the present invention is useful as a heat generation improver for rubber, and a rubber composition containing it is It can be seen that the heat generation improvement effect is remarkable.
平成2年 ど月 2日 1、事件の表示 平成2年特許願 第116431号1990 moon 2 days 1. Display of incident 1990 Patent Application No. 116431
Claims (6)
化合物。 ▲数式、化学式、表等があります▼( I ) [式中、R_1は水素原子、アルキル基、ニトロ基のい
ずれかを表わし、R_2及びR_3はそれぞれ独立して
水素原子、アルキル基、フェニル基、ナフチル基、p−
トルエンスルホニル基のいずれかを表わし、R_4はア
ルキル基、ハロゲン基、アルコキシ基、アセトアミド基
、ニトロ基、アミノ基、カルボキシル基から選ばれた一
種以上の基を表わし、nは0〜4の整数を表わす。](1) A phenylenediamine compound represented by the general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, R_1 represents a hydrogen atom, an alkyl group, or a nitro group, and R_2 and R_3 each independently represent a hydrogen atom, an alkyl group, a phenyl group, naphthyl group, p-
Represents any toluenesulfonyl group, R_4 represents one or more groups selected from an alkyl group, a halogen group, an alkoxy group, an acetamido group, a nitro group, an amino group, and a carboxyl group, and n is an integer of 0 to 4. represent. ]
合物。 ▲数式、化学式、表等があります▼(II) [式中、R_1は水素原子、アルキル基、ニトロ基のい
ずれかを表わし、R_2及びR_3はそれぞれ独立して
水素原子、アルキル基、フェニル基、ナフチル基、p−
トルエンスルホニル基のいずれかを表わし、R_5は水
素原子または炭素数18以下のアルキル基、アリル基、
炭素数6以下のシクロアルキル基を表わし、R_6及び
R_7はそれぞれ独立して水素原子、アルキル基、ヒド
ロキシアルキル基のいずれかを表わす。](2) A phenylenediamine compound represented by general formula (II). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) [In the formula, R_1 represents a hydrogen atom, an alkyl group, or a nitro group, and R_2 and R_3 each independently represent a hydrogen atom, an alkyl group, a phenyl group, naphthyl group, p-
Represents any toluenesulfonyl group, R_5 is a hydrogen atom or an alkyl group having 18 or less carbon atoms, an allyl group,
It represents a cycloalkyl group having 6 or less carbon atoms, and R_6 and R_7 each independently represent a hydrogen atom, an alkyl group, or a hydroxyalkyl group. ]
/または特許請求の範囲第2項記載の一般式(II)で示
されるフェニレンジアミン系化合物を配合してなるゴム
組成物。(3) A rubber composition containing a phenylenediamine compound represented by the general formula (I) described in claim 1 and/or the general formula (II) described in claim 2.
/または特許請求の範囲第2項記載の一般式(II)で示
されるフェニレンジアミン系化合物をゴムの発熱改良剤
として配合してなるゴム組成物。(4) A phenylenediamine compound represented by the general formula (I) described in claim 1 and/or the general formula (II) described in claim 2 is blended as a heat generation improver for rubber. rubber composition.
/または特許請求の範囲第2項記載の一般式(II)で示
されるフェニレンジアミン系化合物の一種または二種以
上を天然ゴム及び/またはジエン系合成ゴムからなるゴ
ム100重量部に、0.1〜10重量部を配合してなる
特許請求の範囲第3項または第4項記載のゴム組成物。(5) One or more phenylenediamine compounds represented by the general formula (I) described in claim 1 and/or the general formula (II) described in claim 2 are added to natural rubber. The rubber composition according to claim 3 or 4, wherein 0.1 to 10 parts by weight is blended with 100 parts by weight of rubber made of diene-based synthetic rubber.
量部に対して、特許請求の範囲第1項記載の一般式(
I )及び/または特許請求の範囲第2項記載の一般式(
II)で示されるフェニレンジアミン系化合物を0.1〜
10重量部、カーボンブラックを20〜150重量部配
合してなるゴム組成物。(6) For 100 parts by weight of natural rubber and/or diene-based synthetic rubber, the general formula (
I) and/or the general formula (
II) phenylenediamine compound shown in 0.1~
A rubber composition containing 10 parts by weight and 20 to 150 parts by weight of carbon black.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2116431A JPH0482879A (en) | 1990-05-01 | 1990-05-01 | Phenylenediamine-based compound and rubber composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2116431A JPH0482879A (en) | 1990-05-01 | 1990-05-01 | Phenylenediamine-based compound and rubber composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0482879A true JPH0482879A (en) | 1992-03-16 |
Family
ID=14686934
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2116431A Pending JPH0482879A (en) | 1990-05-01 | 1990-05-01 | Phenylenediamine-based compound and rubber composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0482879A (en) |
-
1990
- 1990-05-01 JP JP2116431A patent/JPH0482879A/en active Pending
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