JPH0395192A - Azo compound - Google Patents
Azo compoundInfo
- Publication number
- JPH0395192A JPH0395192A JP23447989A JP23447989A JPH0395192A JP H0395192 A JPH0395192 A JP H0395192A JP 23447989 A JP23447989 A JP 23447989A JP 23447989 A JP23447989 A JP 23447989A JP H0395192 A JPH0395192 A JP H0395192A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- reaction
- chloride
- azo compound
- 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
- -1 Azo compound Chemical class 0.000 title claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 17
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 16
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 11
- 239000002253 acid Substances 0.000 abstract description 4
- 239000007870 radical polymerization initiator Substances 0.000 abstract description 2
- UTQFNQPEICUTTN-UHFFFAOYSA-N C(C)OC(OCC)[SiH2]CCCNC(CCC(C)C#N)=O Chemical compound C(C)OC(OCC)[SiH2]CCCNC(CCC(C)C#N)=O UTQFNQPEICUTTN-UHFFFAOYSA-N 0.000 abstract 1
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000005370 alkoxysilyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- FSZXGAPMAKXKFK-UHFFFAOYSA-N 4-cyanopentanamide Chemical compound N#CC(C)CCC(N)=O FSZXGAPMAKXKFK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Polymerization Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、アゾ化合物に関する。[Detailed description of the invention] Industrial applications The present invention relates to azo compounds.
従来の技術及び発明が解決しようとする課題高分子化合
物の製造には、アゾビスイソブチロニトリルやアゾビス
−２．４−ジメチルバレロニトリル等が使用されている
。これらの化合物は、ラジカル重合開始剤として重合反
応を開始し、ポリマー末端に開始剤の一部が結合するこ
とが知られている。Problems to be Solved by the Prior Art and the Invention In the production of polymer compounds, azobisisobutyronitrile, azobis-2,4-dimethylvaleronitrile, and the like are used. It is known that these compounds initiate a polymerization reaction as a radical polymerization initiator, and a portion of the initiator is bonded to the end of the polymer.
ポリマーの物性を改良するために、アルコキシシリル基
を有する重合開始剤の出現が要望されている。この開始
剤を使用することによって、ボリマー末端にアルコキシ
シリル基を導入することが可能とみられるためである。In order to improve the physical properties of polymers, there is a demand for a polymerization initiator having an alkoxysilyl group. This is because it seems possible to introduce an alkoxysilyl group to the polymer terminal by using this initiator.
アルコキシシリル基を有するアゾ化合物の開発が望まれ
ている所以である。This is why the development of azo compounds having an alkoxysilyl group is desired.
ＵＳＰ第３７７５３８６号明細書やＪ．Ａｐｐｌ．Ｓｃ
ｉ，．１８．３２５９ （１９７４）には、下記一般式
（１）で表わされるアゾ化合物が開示されている。USP No. 3775386 and J. Appl. Sc
i,. 18.3259 (1974) discloses an azo compound represented by the following general formula (1).
［式中Ｒｌ 、Ｒ２及びＲ３はアルコキシ基、Ｒ４はア
ルキル基、Ｙは炭素数１〜８の飽和アルケニル基を示す
。］
しかしながら、斯かるアゾ化合物を製造する際には下記
に示すような欠点があり、該アゾ化合物を工業的規模で
製造し得ないという難点を有している。即ち、一般式（
１）のアゾ化合物の製造原料は工業的には入手が困難で
あり、また一般式（１）のアゾ化合物の製造に当って反
応工程が長く、目的化合物の収率が低く、しかも高価な
白金触媒を必要とする等の重大な欠点を有している。[In the formula, R1, R2 and R3 are an alkoxy group, R4 is an alkyl group, and Y is a saturated alkenyl group having 1 to 8 carbon atoms. ] However, when producing such an azo compound, there are the following drawbacks, and it is difficult to produce the azo compound on an industrial scale. That is, the general formula (
The raw materials for producing the azo compound of formula (1) are difficult to obtain industrially, and the reaction process for producing the azo compound of general formula (1) is long, the yield of the target compound is low, and expensive platinum is required. It has serious drawbacks such as requiring a catalyst.
課題を解決するための手段及び効果
本発明者は、斯かる現状に鑑み、上記欠点を有さないア
ゾ化合物の開発に鋭意研究を重ね、ついに本発明を完成
するに至った。Means and Effects for Solving the Problems In view of the current situation, the present inventor has conducted intensive research to develop an azo compound that does not have the above-mentioned drawbacks, and has finally completed the present invention.
即ち、本発明は、一般式 数、ｎは１〜５の整数を示す。コ で表わされるアゾ化合物に係る。That is, the present invention provides the general formula The number n represents an integer of 1 to 5. Ko It pertains to an azo compound represented by
本明細書において、アルキル基としては、炭素数１〜１
０のものが好ましく、中でもメチル、エチル、ｎ−プロ
ビル、イソプロビル、ｎ−ブチル、イソプチル、Ｓｅｃ
−ブチル、ｎ−ペンチル、ｒｌ一ヘキシル基等の炭素数
１〜６の直鎖又は分枝鎖状アルキル基が特に好ましい。In this specification, the alkyl group has 1 to 1 carbon atoms.
0 is preferred, among which methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, Sec.
Particularly preferred are straight-chain or branched alkyl groups having 1 to 6 carbon atoms, such as -butyl, n-pentyl, and rl-hexyl.
本発明の化合物は、例えば下記に示す方法に従い容易に
製造される。The compound of the present invention can be easily produced, for example, according to the method shown below.
［式中Ｒ及びＲ′はアルキル基、ｍは１〜３の整即ち、
本発明化合物は、４．４′ −アゾビスシアノ吉草酸と
塩化チオニルとから酸塩化物を得、次いでこれに例えば
３−アミノプロピルトリアルコキシシラン等のシリルア
ルキルアミノ化合物を反応させることにより容易に製造
される。[In the formula, R and R' are an alkyl group, m is an integer of 1 to 3,
The compound of the present invention can be easily produced by obtaining an acid chloride from 4,4'-azobiscyanovaleric acid and thionyl chloride, and then reacting this with a silylalkyl amino compound such as 3-aminopropyltrialkoxysilane. Ru.
酸塩化物を得るには、通常塩化チオニルを理論量乃至過
剰量使用して４，４′ −アゾビスシアノ吉草酸と塩化
チオニルとを反応させる。反応温度は、通常５０℃以下
、好ましくは４０℃以下とするのがよい。過剰の塩化チ
オニルは、反応終了後、減圧濃縮して除去するのが好ま
しい。該反応は、適当な溶媒中又は無溶媒下、好ましく
は無溶媒下で行なわれる。斯くして得られる酸塩化物は
、そのまま次に反応に供してもよいし、溶媒により洗浄
したり再結晶により精製した後、次の反応に供してもよ
い。To obtain the acid chloride, 4,4'-azobiscyanovaleric acid and thionyl chloride are reacted, usually using thionyl chloride in a stoichiometric amount to an excess amount. The reaction temperature is generally 50°C or lower, preferably 40°C or lower. Excess thionyl chloride is preferably removed by concentration under reduced pressure after the reaction is completed. The reaction is carried out in a suitable solvent or without a solvent, preferably without a solvent. The acid chloride thus obtained may be subjected to the next reaction as it is, or may be subjected to the next reaction after being washed with a solvent or purified by recrystallization.
次に酸塩化物とシリルアルキルアミノ化合物との反応は
、両者を理論量、又はいずれかの原料が若干過剰量とな
るように使用し、不活性溶媒中で行なうのがよい。不活
性溶媒としては、特に限定されるものではないが、例え
ば塩化メチレン、クロロホルム等のハロゲン化炭化水素
類を好適に使用できる。該反応は、脱塩酸反応であり、
反応促進のために常法に従い、ピリジン、トリエチルア
ミン等の脱酸剤を使用するのが望ましい。該反応は、通
常５０℃以下、好ましくは２０℃以下で好適に進行する
。Next, the reaction between the acid chloride and the silylalkyl amino compound is preferably carried out in an inert solvent using both in stoichiometric amounts or in a slightly excess amount of one of the raw materials. The inert solvent is not particularly limited, but halogenated hydrocarbons such as methylene chloride and chloroform can be suitably used. The reaction is a dehydrochlorination reaction,
In order to accelerate the reaction, it is desirable to use a deoxidizing agent such as pyridine or triethylamine according to a conventional method. The reaction normally proceeds suitably at a temperature of 50°C or lower, preferably 20°C or lower.
斯くして得られる本発明の化合物は、通常行なわれてい
る分離精製手段に従い、反応混合物から単離精製される
。The compound of the present invention thus obtained is isolated and purified from the reaction mixture according to commonly used separation and purification means.
上記製造法によれば、原料化合物はいずれも容易に入手
可能な化合物であり、また反応工程も短く、本発明化合
物を収率よく製造し得、しかも本発明化合物製造の際に
高価な白金触媒を使用する必要もない。従って、上記製
造法によれば、本発明化合物を工業的規模で安価に供給
できる。According to the above production method, all the raw material compounds are easily available compounds, the reaction steps are short, the compound of the present invention can be produced in good yield, and the expensive platinum catalyst is used to produce the compound of the present invention. There is no need to use . Therefore, according to the above production method, the compound of the present invention can be supplied on an industrial scale at low cost.
実施例
以下に実施例を掲げ本発明をより一層明らかにするが、
本発明はこれに限定されるものではない。Examples The following examples are given to further clarify the present invention.
The present invention is not limited to this.
実施例１
攪拌機、還流冷却器及び塩化カルシウム管を付した四つ
ロフラスコに、塩化チオニル２ ７ ４ ｘｉを入れ、
５〜１０℃に冷却、攪拌しながらアゾビスシアノ吉草酸
９６ｇを約２時間かけて少量ずつ投入する。その後３５
℃で４時間反応させた後、塩化チオニルを減圧除去し、
酸塩化物を９６ｇ得る。Example 1 Thionyl chloride 2 7 4 xi was placed in a four-loaf flask equipped with a stirrer, reflux condenser and calcium chloride tube,
While cooling to 5-10°C and stirring, 96 g of azobiscyanovaleric acid was added little by little over about 2 hours. then 35
After reacting at ℃ for 4 hours, thionyl chloride was removed under reduced pressure,
96 g of acid chloride are obtained.
収率８９％
次に四つ口フラスコ中に塩化メチレン、３−アミノプロ
ビルトリエトキシシラン１５．４ｇ及びトリエチルアミ
ン６．４ｇを入れ、１０℃以下に冷却する。窒素ガスを
フラスコ内に流しながら、酸塩化物１０ｇを塩化メチレ
ン５０１ｌに溶解し、攪拌下０． ５時間で滴下し、
２時間反応を続ける。Yield: 89% Next, methylene chloride, 15.4 g of 3-aminopropyltriethoxysilane and 6.4 g of triethylamine are placed in a four-necked flask, and the mixture is cooled to below 10°C. While flowing nitrogen gas into the flask, 10 g of acid chloride was dissolved in 501 liters of methylene chloride, and 0.0 g was dissolved under stirring. Dropped in 5 hours,
Continue the reaction for 2 hours.
反応液を減圧濃縮すると粗製物が得られる。粗製物より
エーテル抽出し、炉過後エーテルを減圧除去し、ｎ−へ
キサンで洗浄することにより、目的とする一般式（２）
の化合物（Ｒ＝エチル基、ｍ＝３、ｎ＝３）１８ｇを得
る。収率８３％得られる化合物は淡褐色のペーストであ
り、含量は９６％である。該化合物のＩＲスペクトル図
を第１図に示す。The reaction solution is concentrated under reduced pressure to obtain a crude product. The desired general formula (2) is obtained by extracting ether from the crude product, removing the ether under reduced pressure after passing through a furnace, and washing with n-hexane.
18 g of the compound (R=ethyl group, m=3, n=3) are obtained. The compound obtained with a yield of 83% is a pale brown paste with a content of 96%. The IR spectrum of this compound is shown in FIG.
実施例２
四つロフラスコ中に塩化メチレン１５０ｚＡ’、３−ア
ミノプ口ピルジェトキシメチルシラン１３．４ｇ及びト
リエチルアミン７．０ｇを入れ、１０℃以下に冷却する
。窒素ガスをフラスコ内に流しながら、実施例１に示し
た方法で得られた４．４′−アゾビスシアノ吉草酸クロ
ライド１０ｇを塩化メチレン５０１ｌに溶解し、攪拌下
０． ５時間で滴下し、３時間反応を続ける。反応液
を減圧濃縮すると粗製物が得られる。粗製物よりエーテ
ル抽出し、炉過後エーテルを減圧除去し、ｎ−ヘキサン
で洗浄することにより、目的とする４．４′一アゾビス
（Ｎ−ジエトキシメチルシリルプ口ビル，４−シアノペ
ンタンアミド’）１７．０ｇを得る（収率８６％）。元
素分析値及びＩＲスペクトルからその生成を確認した。Example 2 150 zA' of methylene chloride, 13.4 g of 3-aminopyrjethoxymethylsilane and 7.0 g of triethylamine are placed in a four-bottle flask and cooled to below 10°C. While flowing nitrogen gas into the flask, 10 g of 4,4'-azobiscyanovaleric acid chloride obtained by the method shown in Example 1 was dissolved in 501 liters of methylene chloride, and 0.0 g was dissolved under stirring. It was added dropwise in 5 hours and the reaction was continued for 3 hours. The reaction solution is concentrated under reduced pressure to obtain a crude product. The crude product is extracted with ether, filtered through a furnace, the ether is removed under reduced pressure, and washed with n-hexane to obtain the desired 4.4'-azobis(N-diethoxymethylsilylpylbutylene,4-cyanopentanamide'). ) 17.0 g (yield 86%) are obtained. Its formation was confirmed from elemental analysis values and IR spectrum.
実施例３
３−アミノプロビルジエトキシメチルシランの代りに３
−アミノプロピルトリメトキシシラン１２．６ｇを用い
、実施例２と同様にして、目的とする４．４′−アゾビ
ス（Ｎ−トリメトキシシリルプロピル・，４−シアノペ
ンタンアミド）１５．９ｇを得る（収率８４％）。元素
分析値及びＩＲスペクトルからその生成を確認した。Example 3 3 instead of 3-aminopropyldethoxymethylsilane
Using 12.6 g of -aminopropyltrimethoxysilane, 15.9 g of the desired 4,4'-azobis(N-trimethoxysilylpropyl.,4-cyanopentanamide) was obtained in the same manner as in Example 2 ( yield 84%). Its formation was confirmed from elemental analysis values and IR spectrum.
第１図は、実施例１で得られる化合物のＩＲスペクトル
図である。
（以 上）FIG. 1 is an IR spectrum diagram of the compound obtained in Example 1. (that's all)
Claims (1)
ｎは１〜５の整数を示す。］ で表わされるアゾ化合物。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R and R' are alkyl groups, m is an integer from 1 to 3,
n represents an integer of 1 to 5. ] An azo compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23447989A JP2787343B2 (en) | 1989-09-08 | 1989-09-08 | Azo compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23447989A JP2787343B2 (en) | 1989-09-08 | 1989-09-08 | Azo compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0395192A true JPH0395192A (en) | 1991-04-19 |
| JP2787343B2 JP2787343B2 (en) | 1998-08-13 |
Family
ID=16971663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23447989A Expired - Fee Related JP2787343B2 (en) | 1989-09-08 | 1989-09-08 | Azo compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2787343B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006341537A (en) * | 2005-06-10 | 2006-12-21 | Nisshin Fire & Marine Insurance Co Ltd | Application paper for insurance contract, and method and apparatus for forming guiding information for insurance contract |
| JP2013523671A (en) * | 2010-03-29 | 2013-06-17 | エボニック デグサ ゲーエムベーハー | Method for producing silicon-containing azodicarbamide |
| JP2014201700A (en) * | 2013-04-08 | 2014-10-27 | 東洋ゴム工業株式会社 | Physical property modifier for rubber or plastic, manufacturing method therefor and rubber composition |
| JP2015528026A (en) * | 2012-06-08 | 2015-09-24 | アーゼッド・エレクトロニック・マテリアルズ（ルクセンブルグ）ソシエテ・ア・レスポンサビリテ・リミテ | Neutral layer polymer composition and method for induced self-assembly |
-
1989
- 1989-09-08 JP JP23447989A patent/JP2787343B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006341537A (en) * | 2005-06-10 | 2006-12-21 | Nisshin Fire & Marine Insurance Co Ltd | Application paper for insurance contract, and method and apparatus for forming guiding information for insurance contract |
| JP2013523671A (en) * | 2010-03-29 | 2013-06-17 | エボニック デグサ ゲーエムベーハー | Method for producing silicon-containing azodicarbamide |
| JP2015528026A (en) * | 2012-06-08 | 2015-09-24 | アーゼッド・エレクトロニック・マテリアルズ（ルクセンブルグ）ソシエテ・ア・レスポンサビリテ・リミテ | Neutral layer polymer composition and method for induced self-assembly |
| JP2014201700A (en) * | 2013-04-08 | 2014-10-27 | 東洋ゴム工業株式会社 | Physical property modifier for rubber or plastic, manufacturing method therefor and rubber composition |
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| JP2787343B2 (en) | 1998-08-13 |
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