JPH0635487B2 - Optically active polymerization catalyst - Google Patents
Optically active polymerization catalystInfo
- Publication number
- JPH0635487B2 JPH0635487B2 JP8169685A JP8169685A JPH0635487B2 JP H0635487 B2 JPH0635487 B2 JP H0635487B2 JP 8169685 A JP8169685 A JP 8169685A JP 8169685 A JP8169685 A JP 8169685A JP H0635487 B2 JPH0635487 B2 JP H0635487B2
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- polymerization catalyst
- present
- polymerization
- active polymerization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002685 polymerization catalyst Substances 0.000 title claims description 11
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 11
- 239000003505 polymerization initiator Substances 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 8
- -1 carbon anions Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VCVPSRADUBPOKJ-NSHDSACASA-N 1-[[(2s)-1-methylpyrrolidin-2-yl]methyl]piperidine Chemical compound CN1CCC[C@H]1CN1CCCCC1 VCVPSRADUBPOKJ-NSHDSACASA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- YUWSXYQUCFBRQW-UHFFFAOYSA-N [diphenyl(pyridin-2-yl)methyl] 2-methylprop-2-enoate Chemical compound C=1C=CC=CC=1C(C=1N=CC=CC=1)(OC(=O)C(=C)C)C1=CC=CC=C1 YUWSXYQUCFBRQW-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- NOUUUQMKVOUUNR-UHFFFAOYSA-N n,n'-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1NCCNC1=CC=CC=C1 NOUUUQMKVOUUNR-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- PTVDYMGQGCNETM-UHFFFAOYSA-N trityl 2-methylprop-2-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC(=O)C(=C)C)C1=CC=CC=C1 PTVDYMGQGCNETM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Polymerization Catalysts (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は特定の不斉配位子とアニオン重合開始剤とから
なる光学活性な重合触媒及び該光学活性な重合触媒を用
いて、重合性単量体を重合させて光学活性な高分子を得
ることを特徴とする光学活性な高分子の合成法に関する
ものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention is directed to an optically active polymerization catalyst comprising a specific asymmetric ligand and an anionic polymerization initiator, and a polymerizable polymer using the optically active polymerization catalyst. The present invention relates to a method for synthesizing an optically active polymer, which comprises polymerizing a monomer to obtain an optically active polymer.
本発明者らは、光学活性な高分子を得る重合用触媒とし
て不斉重合触媒を見い出し既に特願昭５７−０３６９０
９号（特開昭５８−１５４７０３）、特願昭５８−１７
６４７３号明細書に開示しているが、さらに鋭意検討
し、通常、不斉合成に用いられている不斉配位子も光学
活性な高分子を得る重合触媒となり得ることを見い出し
本発明に到つた。The present inventors have found an asymmetric polymerization catalyst as a polymerization catalyst for obtaining an optically active polymer, and have already found Japanese Patent Application No. 57-03690.
No. 9 (JP-A-58-154703), Japanese Patent Application No. 58-17
Although disclosed in the Japanese Patent No. 6473, the present invention has been further studied and found that an asymmetric ligand usually used for asymmetric synthesis can also serve as a polymerization catalyst for obtaining an optically active polymer, leading to the present invention. Ivy.
即ち、本発明は一般式(I) （式中、＊は不斉炭素原子を示し、R1は炭素数１〜20の
直鎖状あるいは分岐鎖を有する炭化水素基であり、その
構造中に２重結合又は芳香族炭化水素を含んでいてもか
まわない。）で表わされる不斉配位子と、アニオン重合
開始剤とからなることを特徴とする光学活性な重合用触
媒に係るものである。That is, the present invention is represented by the general formula (I) (In the formula, * represents an asymmetric carbon atom, R 1 is a linear or branched hydrocarbon group having 1 to 20 carbon atoms, and the structure thereof includes a double bond or an aromatic hydrocarbon. The present invention relates to an optically active polymerization catalyst characterized by comprising an asymmetric ligand represented by the formula (1) and an anionic polymerization initiator.
本発明に用いられる上記一般式(I)で表わされる不斉配
位子として好ましいものは、R1で示される基がメチル基
又はエチル基のものである。The preferred asymmetric ligand represented by the above general formula (I) used in the present invention is one in which the group represented by R 1 is a methyl group or an ethyl group.
本発明の光学活性な重合触媒を構成するためのアニオン
重合開始剤は、前記不斉配位子と錯体をつくり得るもの
であればいかなるものでも良い。具体的には対イオンと
してのアルカリ金属、アルカリ土類金属、アルミニウ
ム、又は類似金属と、アニオンとしての炭素、窒素、酸
素、イオウなどのアニオンから成るアニオン重合開始剤
が用いられる。好ましいものは、炭素のアニオンからな
るアニオン重合開始剤であり、例示すれば、次のような
ものである。The anionic polymerization initiator for forming the optically active polymerization catalyst of the present invention may be any one as long as it can form a complex with the asymmetric ligand. Specifically, an anionic polymerization initiator comprising an alkali metal, an alkaline earth metal, aluminum or a similar metal as a counter ion and an anion such as carbon, nitrogen, oxygen or sulfur as an anion is used. Preferred are anionic polymerization initiators composed of carbon anions, and the following are exemplified.
RMgX，R2Mg，RCaX，Al(C2H5)3，LiR，LiAlH4，NaR，KR
（但しＲはブチル、ベンジル、フエニル基などの炭素数
１〜50、好ましくは１〜20のアルキル基、アルアルキル
基又は芳香族基で、Ｘはハロゲンである）。RMgX, R 2 Mg, RCaX, Al (C 2 H 5 ) 3 , LiR, LiAlH 4 , NaR, KR
(However, R is an alkyl group having 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, such as a butyl, benzyl or phenyl group, an aralkyl group or an aromatic group, and X is a halogen).
アルアルキル基を有するアニオン開始剤としては次の様
なものが挙げられる。Examples of the anionic initiator having an aralkyl group include the following.
又、窒素のアニオン、即ち２級アミンから得られるアニ
オン重合開始剤も好ましく用いられる。かかるアニオン
重合開始剤を例示するならば次のようなものがある。 Further, an anionic polymerization initiator obtained from a nitrogen anion, that is, a secondary amine is also preferably used. Examples of such an anionic polymerization initiator are as follows.
（但し、Ｒ′，Ｒ″は炭素数１〜50、好ましくは１〜20
のアルキル基、アルアルキル基又は芳香族基であり、Ｍ
は対イオンである。） 又、リチウムアミドのアニオンとして用いられる２級ア
ミンとしては次の様なものが挙げられる。 (However, R'and R "have 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms.
An alkyl group, an aralkyl group or an aromatic group of
Is a counterion. The secondary amine used as the anion of lithium amide includes the following.
本発明の光学活性な重合用触媒の調製法として好ましい
方法は、アニオン重合開始剤と、このアニオン重合開始
剤に対して等モルか若干多めの脱水乾燥した上記一般式
(I)で表わされる不斉配位子とを溶媒中、例えば炭化水
素溶媒中で混合し錯体を形成させる方法である。 The preferred method for preparing the optically active polymerization catalyst of the present invention is an anionic polymerization initiator and the above-mentioned general formula dehydrated and dried in an equimolar amount or a little more than the anionic polymerization initiator.
This is a method of forming a complex by mixing the asymmetric ligand represented by (I) in a solvent, for example, a hydrocarbon solvent.
本発明の重合用触媒を用いて重合性単量体を重合させる
に当つては、重合性単量体は重合性単量体のみでもよい
が、溶媒に溶かして重合させてもよい。この場合、用い
る溶媒はアニオン重合を阻害するものであつてはならな
い。When the polymerizable monomer is polymerized by using the polymerization catalyst of the present invention, the polymerizable monomer may be only the polymerizable monomer or may be dissolved in a solvent and polymerized. In this case, the solvent used must not inhibit anionic polymerization.
本発明の光学活性な高分子の合成に用いられる重合性単
量体としては、ビニル基を有するものであれば、いかな
るものでも良い。The polymerizable monomer used in the synthesis of the optically active polymer of the present invention may be any one having a vinyl group.
具体的にはメタクリル酸エステルなどのα−置換アクリ
ル酸エステル、アクリル酸エステル、Ｎ−置換マレイミ
ド、N,N−ジ置換又はＮ−モノ置換のアクリルアミド及
びメタクリルアミド、スチレン及びスチレン誘導体、共
役ジエン類、メタクリロニトリル、アクリロニトリル、
ビニルピリジン等である。Specifically, α-substituted acrylates such as methacrylic acid esters, acrylic acid esters, N-substituted maleimides, N, N-disubstituted or N-monosubstituted acrylamides and methacrylamides, styrene and styrene derivatives, conjugated dienes. , Methacrylonitrile, acrylonitrile,
Vinyl pyridine and the like.
以下、実施例によつて本発明を具体的に説明するが、本
発明はこれらによつて限定されるものではない。Hereinafter, the present invention will be described specifically with reference to Examples, but the present invention is not limited thereto.
合成例１ 光学活性配位(S)−１−メチル−２−（ピペリジノメチ
ル）ピロリドンの合成 カルボベンゾオキシ−Ｌ−プロリンを出発物質として、
既知の方法（Chem.Lett.，1982，1441）に従つて、20％
の収率で光学活性配位(S)−１−メチル−２−（ピペリ
ジノメチル）ピロリジンを合成した。Synthesis Example 1 Synthesis of Optically Active Coordination (S) -1-Methyl-2- (piperidinomethyl) pyrrolidone Starting from carbobenzooxy-L-proline,
20% according to the known method (Chem. Lett., 1982, 1441)
The optically active coordination (S) -1-methyl-2- (piperidinomethyl) pyrrolidine was synthesized with the following yield.
実施例１ (S)−１メチル−２−（ピペリジノメチル）ピロリジン
−N,N′−ジフエニルエチレンジアミンモノリチウムア
ミド錯体によるトルエン中、−７８℃でのメタクリル酸
トリフエニルメチルの不斉重合を次の様に行なつた。Example 1 (S) -1 Methyl-2- (piperidinomethyl) pyrrolidine-N, N'-diphenylethylenediamine monolithium amide complex in toluene at -78 [deg.] C. Like that.
即ち、重合は十分に乾燥したガラス封管中、窒素気流下
で行なつた。まず、トルエン20mlにメタクリル酸トリフ
エニルメチル1.00ｇ（3.05m mol）を溶解させ、これを
−７８℃にした。That is, the polymerization was carried out in a sufficiently dried glass sealed tube under a nitrogen stream. First, 1.00 g (3.05 mmol) of triphenylmethyl methacrylate was dissolved in 20 ml of toluene, and this was brought to -78 ° C.
又、別に、室温、ヘキサン中でBuLiと当量のN,N′−ジ
フエニルエチレンジアミンを反応させてN,N′−ジフエ
ニルエチレンジアミンのモノリチウムアミド を合成し、その1.2倍当量の不斉配位子化合物(S)−１−
メチル−２−（ピペリジノメチル）ピロリジンを加えて
錯体を合成し、触媒とした。この触媒を前記モノマーの
トルエン溶液に加えて重合を開始した。Separately, BuLi was reacted with an equivalent amount of N, N'-diphenylethylenediamine in hexane at room temperature to prepare a monolithium amide of N, N'-diphenylethylenediamine. Was synthesized, and 1.2 times equivalent of the asymmetric ligand compound (S) -1-
Methyl-2- (piperidinomethyl) pyrrolidine was added to synthesize a complex, which was used as a catalyst. This catalyst was added to a toluene solution of the above monomer to initiate polymerization.
重合は少量のメタノールで停止させ、ポリマーを200ml
のメタノールに沈澱させ、遠心分離し、乾燥後秤量し
た。ポリマーは定量的に生成し、すべてテトラヒドロフ
ラン（ＴＨＦ）に可溶であつた。ポリマーの比旋光度
（▲〔α〕25 589▼）は−３０９゜（ＴＨＦ中）であつ
た。旋光度は日本分光ＤＩＰ−１８１を用いて測定し
た。Polymerization was stopped with a small amount of methanol and 200 ml of polymer was added.
Of methanol, centrifuged, dried and weighed. The polymer was produced quantitatively and was all soluble in tetrahydrofuran (THF). The specific optical rotation of the polymer (▲ [α] 25 589 ▼) was −309 ° (in THF). The optical rotation was measured using JASCO DIP-181.
表−１に重合条件、得られたポリマーの収率、比旋光度
をまとめて示す。Table 1 collectively shows the polymerization conditions, the yield of the obtained polymer and the specific optical rotation.
実施例２ 実施例１と同様にして、フルオレンとBuLiを反応させ
て、フルオレニルメチルリチウムを合成し、その1.2倍
当量の不斉配位子(S)−１−メチル−２−（ピペリジノ
メチル）ピロリジンを加えて錯体を合成し、重合を行な
つた。表−１に重合条件、得られたポリマーの収率、比
旋光度をまとめて示す。Example 2 In the same manner as in Example 1, fluorene and BuLi were reacted to synthesize fluorenylmethyllithium, and 1.2 times equivalent of the asymmetric ligand (S) -1-methyl-2- (piperidinomethyl). ) Pyrrolidine was added to synthesize a complex, and polymerization was performed. Table 1 collectively shows the polymerization conditions, the yield of the obtained polymer and the specific optical rotation.
実施例３ メタクリル酸ジフエニル−２−ピリジルメチル（1.0
ｇ）を実施例１と同様の触媒を用いて重合させた。表−
１に重合条件、得られたポリマーの収率、比旋光度をま
とめて示す。Example 3 Diphenyl-2-pyridylmethyl methacrylate (1.0
g) was polymerized using the same catalyst as in Example 1. Table-
The polymerization conditions, the yield of the obtained polymer and the specific optical rotation are collectively shown in 1.
実施例４ メタクリル酸ジフエニル−２−ピリジルメチル（1.0
ｇ）を実施例２と同様の触媒を用いて重合させた。表−
１に重合条件、得られたポリマーの収率、比旋光度をま
とめて示す。Example 4 Diphenyl-2-pyridylmethyl methacrylate (1.0
g) was polymerized using the same catalyst as in Example 2. Table-
The polymerization conditions, the yield of the obtained polymer and the specific optical rotation are collectively shown in 1.
Claims (1)
直鎖状あるいは分岐鎖を有する炭化水素基であり、その
構造中に２重結合又は芳香族炭化水素を含んでいてもか
まわない。）で表わされる不斉配位子と、アニオン重合
開始剤とからなることを特徴とする光学活性な重合用触
媒。1. A general formula (I) (In the formula, * represents an asymmetric carbon atom, R 1 is a linear or branched hydrocarbon group having 1 to 20 carbon atoms, and the structure thereof includes a double bond or an aromatic hydrocarbon. An optically active polymerization catalyst comprising an asymmetric ligand represented by the formula (1) and an anionic polymerization initiator.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8169685A JPH0635487B2 (en) | 1985-04-17 | 1985-04-17 | Optically active polymerization catalyst |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8169685A JPH0635487B2 (en) | 1985-04-17 | 1985-04-17 | Optically active polymerization catalyst |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61238801A JPS61238801A (en) | 1986-10-24 |
| JPH0635487B2 true JPH0635487B2 (en) | 1994-05-11 |
Family
ID=13753532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8169685A Expired - Lifetime JPH0635487B2 (en) | 1985-04-17 | 1985-04-17 | Optically active polymerization catalyst |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0635487B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2523803B2 (en) * | 1988-07-26 | 1996-08-14 | ダイセル化学工業株式会社 | Optically active polymerization catalyst and method for synthesizing optically active polymer |
| JP4900688B2 (en) * | 2006-10-19 | 2012-03-21 | 国立大学法人北海道大学 | Optically active polymer compound |
| CN104031182B (en) * | 2014-06-10 | 2016-04-06 | 湘潭大学 | A kind of preparation method of chiral carbon negatively charged ion composite initiator |
-
1985
- 1985-04-17 JP JP8169685A patent/JPH0635487B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| ＰｏｌｙｍｅｒＪｏｕｒｎａｌ，Ｖｏｌ．１３，Ｎｏ．２，ＰＰ．１７９−１８１（１９８１） |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61238801A (en) | 1986-10-24 |
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