JPS63275590A - Butadiene derivative having amino group protected by silyl group - Google Patents
Butadiene derivative having amino group protected by silyl groupInfo
- Publication number
- JPS63275590A JPS63275590A JP10976487A JP10976487A JPS63275590A JP S63275590 A JPS63275590 A JP S63275590A JP 10976487 A JP10976487 A JP 10976487A JP 10976487 A JP10976487 A JP 10976487A JP S63275590 A JPS63275590 A JP S63275590A
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- Japan
- Prior art keywords
- formula
- group
- ether
- compound
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- Prior art date
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 8
- 125000003277 amino group Chemical group 0.000 title description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 27
- 150000001875 compounds Chemical class 0.000 abstract description 18
- 238000010550 living polymerization reaction Methods 0.000 abstract description 6
- 125000000129 anionic group Chemical group 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 4
- -1 diethyl ether Chemical compound 0.000 abstract description 4
- 239000005062 Polybutadiene Substances 0.000 abstract description 3
- 229920002857 polybutadiene Polymers 0.000 abstract description 3
- 125000005103 alkyl silyl group Chemical group 0.000 abstract description 2
- 229910052749 magnesium Inorganic materials 0.000 abstract description 2
- 239000011777 magnesium Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 2
- PCPYTNCQOSFKGG-UHFFFAOYSA-N 1-chlorobuta-1,3-diene Chemical compound ClC=CC=C PCPYTNCQOSFKGG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- LBSXSAXOLABXMF-UHFFFAOYSA-N 4-Vinylaniline Chemical compound NC1=CC=C(C=C)C=C1 LBSXSAXOLABXMF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- NJAUUZAOAYPFSB-UHFFFAOYSA-N bromic acid;3-bromopropan-1-amine Chemical compound OBr(=O)=O.NCCCBr NJAUUZAOAYPFSB-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical compound [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Abstract
Description
【発明の詳細な説明】
本発明は、アミノ基金シリル基で保護し念ブタジェン誘
導体に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to butadiene derivatives protected with amino-based silyl groups.
従来の技術
水酸基、アミノ基、ホルミル基、カルボキシル基等の官
能基を有するビニル化合物の７ニオンリビング重合にお
いては、生長活性末端のカルバニオンの灰石性が高く、
水酸基やアミノ基のプロトン或いはカルボニル基と一瞬
の間に反応してしまうため、これらの官能基を持つモノ
マーにアニオンリビング重合を適用することはできない
。Conventional technology In the 7-ion living polymerization of vinyl compounds having functional groups such as hydroxyl groups, amino groups, formyl groups, carboxyl groups, etc., the carbanion at the growth active terminal has a high ashstone property,
Anionic living polymerization cannot be applied to monomers with these functional groups because they react instantaneously with the protons or carbonyl groups of hydroxyl groups and amino groups.
本発明者らは、先にこれら官能基を保護して、アニオン
リビング重合を可能ならしめる研究をいくつか行ってお
り、発表している。例えば、ｐ−アミノスチレンのアミ
ノ基をトリアルキルシリル基で保護した後、アニオンリ
ビング重合し、脱トリプルキルシリル基によりポリ（ｐ
−アミノスチレン）を得ている。The present inventors have previously conducted and published several studies on protecting these functional groups to enable anionic living polymerization. For example, after protecting the amino group of p-aminostyrene with a trialkylsilyl group, anionic living polymerization is performed, and poly(p
-aminostyrene).
発明が解決しようとする問題点
本発明は、側鎖にアミノ基を有するポリブタジェンの合
成を可能とするアミノ基を保護したブタジェン誘導体を
提供することを目的とする。Problems to be Solved by the Invention An object of the present invention is to provide a butadiene derivative with an amino group protected, which enables the synthesis of polybutadiene having an amino group in its side chain.
発明の要旨
すなわち、本発明は
一般式
〔但し、Ｒ１〜Ｒ＠は同一か異なる炭素数１〜６個のア
ルキル基であり Ｒ１〜Ｈａの任意の−てもよい。ｎ＝
１〜７〕
のブタジェン誘導体を要旨とする。Summary of the Invention That is, the present invention relates to the general formula [However, R1 to R@ are the same or different alkyl groups having 1 to 6 carbon atoms, and R1 to Ha may be any of -. n=
1 to 7] butadiene derivatives.
ブタジェン誘導体の製造法
本発明のブタジェン誘導体は、弐〇Ｈ！−ＣＨ−〇（Ｍ
ｇＯｊ）−（Ｊｈ の２−マグネシウムクロロ−１゜
３−ブタジェン（以下、化合物！という。）と〔但し、
ＲＩ Ｍｙ Ｒ＠は前記と同意義。２はハロゲン原子又
はＯ１２゜ｎ ＝ １〜７゜Ｒ１は炭素数１〜６個のア
ルキル基。〕で示されるＮ ｆｔ換アルキルシリル基含
有化合物（以下、化合物■という、）を、反応させるこ
とによって製造することができる。Method for producing butadiene derivative The butadiene derivative of the present invention is produced by 2〇H! -CH-〇(M
gOj)-(Jh's 2-magnesium chloro-1°3-butadiene (hereinafter referred to as compound!) and [however,
RI My R@ has the same meaning as above. 2 is a halogen atom or O12゜n = 1 to 7゜R1 is an alkyl group having 1 to 6 carbon atoms. ] The N ft -alkylsilyl group-containing compound (hereinafter referred to as compound (2)) can be produced by reacting it.
化合物ｌと化合物層の反応は、通常Ｌｉｌ Ｃ！ｕＣｔ
４＋ｃｕｘｔ（ジフェニルホスフィノエタン）ＮｉＧ４
錯体、ジシクロペンタジェニルチタンジクロリド等の触
媒の存在下、ジエチルエーテル、ジプロピルエーテル、
ジブチルエーテル、シアミルエーテル、アニソール、テ
トラヒドロフラン等のエーテル中にて、０〜１００℃で
１〜１０時間反応させることにより製造することができ
る。The reaction between compound l and the compound layer is usually Lil C! uCt
4+cuxt (diphenylphosphinoethane) NiG4
complex, diethyl ether, dipropyl ether, in the presence of a catalyst such as dicyclopentadienyl titanium dichloride,
It can be produced by reacting in an ether such as dibutyl ether, cyamyl ether, anisole, or tetrahydrofuran at 0 to 100°C for 1 to 10 hours.
化合物層と化合物層は、化合物Ｉ／化合物ｎ（モル比）
＝ １． ｓ〜５の範囲で用いるのが望ましく、又前
記の触媒は、化合物■に対して、通常１５〜５モル僑の
量で用いられる。The compound layer and the compound layer are compound I/compound n (molar ratio)
= 1. It is preferable to use the catalyst in an amount of s to 5, and the above-mentioned catalyst is usually used in an amount of 15 to 5 mol per mol of compound 1.
化合物ＩＯ一般式における２は臭素原子、メトキシ基、
エトキシ基が Ｒ１〜Ｒ６はメチル基、エチル基 ＨＡ
〜Ｒ” （Ｄうちの二つとＲ４−Ｒ６のうちの二つがメ
チル基 Ｒ１−Ｒ１のうちの一つのがそれぞれ望ましく
、ｎは１又は３が望ましい。2 in the general formula of compound IO is a bromine atom, a methoxy group,
Ethoxy group R1 to R6 are methyl group, ethyl group HA
~R'' (Two of D and two of R4-R6 are methyl groups, each of R1-R1 is preferably one, and n is preferably 1 or 3.
発明の効果
本発明のブタジェン誘導体は、容易にアニオンリビング
重合することができ、又保護基のアルキルシリル基は中
性ないし酸性条件下で容易に脱離され、定量的に側鎖に
アミノ基を有するポリブタジェンを製造することができ
る。Effects of the Invention The butadiene derivatives of the present invention can be easily subjected to anionic living polymerization, and the alkylsilyl protecting group can be easily removed under neutral to acidic conditions, and the amino group can be quantitatively added to the side chain. It is possible to produce polybutadiene with
実施例 以下、実施列ｖｃより本発明を説明する。Example The present invention will be explained below based on the implementation column VC.
実施９１１
ブロモプロピルアミンの臭素酸塩４４Ｆ（２０ミリモル
）、トリエチルアミン９ｍ（，６０ミリモル）及び乾燥
した塩化メチレン２０ｄｉ２００−のナス型フラスコに
入れ、これにビスクロロジメチルシリルエタンＣｃｔＣ
ｃ１（、＞富８ｌ−ＣＨ！−Ｃ）！冨−８１（ＣＨｓ）
ｓ（ｔ） ４５ ｆ （２０ミリモル）の塩化メチレ
ン溶液２０−を攪拌しながら滴下し、更に２時間室温で
攪拌を続けた。反応液から塩化メチレンを減圧留去し、
残った固体をヘキサンに溶解し、これを５幅のＮａＯＨ
水溶液で洗浄し念。ヘキサンを留去し、減圧蒸留により
５８憾物ムという）１−得た。この化合物の沸点は５０
℃７１ ｍｕｇ であった。Run 911 Bromopropylamine bromate 44F (20 mmol), triethylamine 9M (.60 mmol) and dry methylene chloride 20 di 200- were placed in an eggplant-shaped flask and added with bischlorodimethylsilylethane CctC.
c1(, > wealth 8l-CH!-C)! Tomi-81 (CHs)
A solution of 20 mmol of s(t) 45 f (20 mmol) in methylene chloride was added dropwise with stirring, and stirring was continued for an additional 2 hours at room temperature. Methylene chloride was distilled off from the reaction solution under reduced pressure,
Dissolve the remaining solid in hexane and dissolve it in 5 portions of NaOH.
Wash it with an aqueous solution. The hexane was distilled off, and 1-1 was obtained by distillation under reduced pressure. The boiling point of this compound is 50
The temperature was 71 mg.
ａｎげ０１１１−０（ＭｇＯｊ）糧Ｃ１１，の合成５０
０−の２ツロフラスコに金属マグネシウムＳａｔ＜１２
０モル）及びテトラヒドロフラン（ＴＨＦ）２０ｄｉ窒
・素雰囲気にて入れ、これにＣＨ３工 ２−のＴＨＦ溶
液を一度に加えた。Synthesis of ange 0111-0 (MgOj) food C11, 50
Magnesium metal Sat<12 in two flasks of 0-
0 mol) and tetrahydrofuran (THF) in a nitrogen/substance atmosphere, and a THF solution of CH3 engineering 2- was added at once to this.
更に、乾燥させたＺｒ５０４１０−加え念、クラスコを
４０〜５０℃に加熱し、攪拌しながらクロロプレン１２
ｆ、 （ＨｓＩ ２−及びＴＨＦ７０ｄからなる
溶１１時間掛けて滴下した。４０〜５０℃温度を保つｆ
ｃまま５０分間攪拌を続けｆｃ。Furthermore, add dried Zr50410, heat Clasco to 40-50°C, and add chloroprene 12 while stirring.
f, (A solution consisting of HsI 2- and THF 70d was added dropwise over 11 hours. Maintaining the temperature at 40-50°C f.
Continue stirring for 50 minutes at c and fc.
得られた溶液をそのまま次のカップリング反応に用いる
。The obtained solution is used as it is in the next coupling reaction.
２００−の２ツロフラスコに、上記で得られた化合物（
４）ｘｏｒ（ｔ１７１７ミリ）及びＬｉ１ＣｕＣ６４（
２，１ミリモル、１モルの’１’１ｌｌＦ溶液２．１
ｍ）を含むＴＨＦ溶液１０−を入れ、これに上記で得ら
れたＯＨピＣＨ−Ｃ（ＭｇＣＬ’）−ＣＨｇ のＴ１１
１Ｆ溶液（１モル溶液を２０−１２０ミリモル）を室温
で１０分間掛けて滴下し、２４時間還流させて反応を完
結させた。反応液に硫酸ナトリウム飽和水溶液を加えて
沈澱物ｅＦ別し、ろ液を減圧濃縮してジエチルエーテル
（以下、エーテルという。）を加え、５僑水酸化ナトリ
ウム水溶液で洗浄し九。The compound obtained above (
4) xor (t1717 mm) and Li1CuC64 (
2.1 mmol, 1 molar '1'1llF solution 2.1
m) containing THF solution 10- was added, and T11 of the OHpiCH-C(MgCL')-CHg obtained above was added to this.
A 1F solution (20-120 mmol of 1 molar solution) was added dropwise over 10 minutes at room temperature, and the reaction was completed by refluxing for 24 hours. A saturated aqueous solution of sodium sulfate was added to the reaction mixture to separate the precipitate eF, the filtrate was concentrated under reduced pressure, diethyl ether (hereinafter referred to as ether) was added, and the mixture was washed with an aqueous sodium hydroxide solution.
硫酸マグネシウムで該エーテル溶液を乾燥後、エーテル
を留去し、残留物を減圧蒸留して沸点８０℃／（Ｌ５■
の生成物ｆ：１． ａ ｔ （収率６７％）得た。After drying the ether solution with magnesium sulfate, the ether was distilled off, and the residue was distilled under reduced pressure to a boiling point of 80°C/(L5
Product f: 1. a t (yield 67%) was obtained.
得られた生成物を’ＨＮＭＲ分析した。その１１ＭＲチ
ャートを第１図に示したが、その結果から得られた生成
物は下記の構造からなる化合物であることが判明した。The obtained product was subjected to 'HNMR analysis. The 11MR chart is shown in FIG. 1, and it was found from the results that the product was a compound having the following structure.
（第１図） （ｆｐＪ１図）ａ
■ ■
ｂ （２） ｆ ■、■Ｃ
■ ｇ ■
ｄ ■
実施例２
実施例１で合成したＯ Ｈｇ −ＣＨ−０（Ｍ ｇ Ｏ
Ｌ ）＝ Ｃ烏のＴＨＦ溶液（１，５モル、２０−）に
、（１！Ｈ，０Ｃ）１！−Ｎ［５ｉ（ＣＨｓ）ｓｈ
６−５６ ｆ （５１ミリモル）を室温で滴下した後室
温で２４時間攪拌した。更に、還流温度で１２時間反応
させた後、硫酸ナトリウム飽和水溶液を加えて、沈澱物
１に炉別し、ろ液を減圧濃縮してエーテルを加え、５ｇ
Ｉ水酸化ナトリウム水溶液で洗浄した。硫酸マグネシウ
ムでエーテル溶液を乾燥後、エーテルを留去し、残留物
から減圧蒸留により２．４ｔ（収率４１憾）の生成物を
得た。生成物の沸点線５５〜６０℃／２■Ｅｇ であ
った。(Fig. 1) (fpJ1) a
■ ■ b (2) f ■, ■C
■ g ■ d ■ Example 2 O Hg -CH-0 (M g O
L)=C Crow in THF solution (1.5 mol, 20-), (1!H,0C)1! -N[5i(CHs)sh
6-56 f (51 mmol) was added dropwise at room temperature, and the mixture was stirred at room temperature for 24 hours. Further, after reacting at reflux temperature for 12 hours, a saturated aqueous solution of sodium sulfate was added, the precipitate 1 was separated in a furnace, the filtrate was concentrated under reduced pressure, and ether was added to give 5 g.
Washed with aqueous sodium hydroxide solution. After drying the ether solution with magnesium sulfate, the ether was distilled off, and the residue was distilled under reduced pressure to obtain 2.4 tons of product (yield: 41). The boiling point line of the product was 55-60°C/2Eg.
得られた生成物のＳＲＭＭＲチャートを第２図に示すが
、その結果から得られた生成物は、下記の構造からなる
化合物であることが判明した。The SRMMR chart of the obtained product is shown in FIG. 2, and it was found from the results that the obtained product was a compound having the following structure.
ケミカルシフト 帰 属 ケミカルシフト 帰
属（第２図） （第２図）ａ
■ ｄ ■）
■ （◇Ｃ■Chemical shift attribution Chemical shift attribution (Figure 2) (Figure 2)a
■ d ■)
■ (◇C■
第１図及び第２図は本発明の化合物のＮＭＲチャートで
ある。FIGS. 1 and 2 are NMR charts of the compounds of the present invention.
Claims (1)
のアルキル基であり、Ｒ＾１〜Ｒ＾３の任意の一個とＲ
＾４〜Ｒ＾６の任意の一個で▲数式、化学式、表等があ
ります▼基を形成してもよい。ｎ＝１〜７。〕 のブタジエン誘導体。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [However, R^1 to R^6 are the same or different alkyl groups having 1 to 6 carbon atoms, and any of R^1 to R^3 one piece and R
Any one of ^4 to R^6 may form a ▲mathematical formula, chemical formula, table, etc.▼ group. n=1-7. ] butadiene derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10976487A JPS63275590A (en) | 1987-05-07 | 1987-05-07 | Butadiene derivative having amino group protected by silyl group |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10976487A JPS63275590A (en) | 1987-05-07 | 1987-05-07 | Butadiene derivative having amino group protected by silyl group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63275590A true JPS63275590A (en) | 1988-11-14 |
Family
ID=14518636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10976487A Pending JPS63275590A (en) | 1987-05-07 | 1987-05-07 | Butadiene derivative having amino group protected by silyl group |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63275590A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009086477A3 (en) * | 2007-12-28 | 2009-09-24 | Bridgestone Corporation | Functionalized polymer and methods for making and using |
| JP2012241133A (en) * | 2011-05-20 | 2012-12-10 | Bridgestone Corp | Rubber composition |
-
1987
- 1987-05-07 JP JP10976487A patent/JPS63275590A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009086477A3 (en) * | 2007-12-28 | 2009-09-24 | Bridgestone Corporation | Functionalized polymer and methods for making and using |
| KR20100111703A (en) * | 2007-12-28 | 2010-10-15 | 가부시키가이샤 브리지스톤 | Functionalized polymer and methods for making and using |
| JP2012241133A (en) * | 2011-05-20 | 2012-12-10 | Bridgestone Corp | Rubber composition |
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