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Synthetic polymers controlled in spiral structure, host-guest compounds prepared by using the same, and processes for production of both

外国特許コード F110003799
整理番号 E07107WO
掲載日 2011年7月5日
出願国 アメリカ合衆国
出願番号 59945508
公報番号 20110144262
公報番号 8383717
出願日 平成20年3月18日(2008.3.18)
公報発行日 平成23年6月16日(2011.6.16)
公報発行日 平成25年2月26日(2013.2.26)
国際出願番号 JP2008000636
国際公開番号 WO2008139674
国際出願日 平成20年3月18日(2008.3.18)
国際公開日 平成20年11月20日(2008.11.20)
優先権データ
  • 特願2007-125098 (2007.5.9) JP
  • 2008JP000636 (2008.3.18) WO
発明の名称 (英語) Synthetic polymers controlled in spiral structure, host-guest compounds prepared by using the same, and processes for production of both
発明の概要(英語) The invention provides a process for producing spiral polymers controlled in the direction of spiral winding easily from inexpensive general-purpose polymers; and spiral polymers controlled in the direction of spiral winding.
The invention relates to a process for the production of syndiotactic polymethacrylate- or polyacrylate-type spiral polymers controlled in the direction of spiral winding which comprises dissolving a syndiotactic polymethacrylate- or polyacrylate-type polymer and a chiral compound in a solvent preferably under heating, subjecting the obtained solution to cooling or concentration to form a solid matter, and separating the solid matter; and so on.
従来技術、競合技術の概要(英語) BACKGROUND ART
It is known that syndiotactic polymethyl methacrylate (hereinafter, may be abbreviated to st-PMMA) forms a spiral structure when an organic solvent such as toluene or acetone is incorporated, and undergoes gelation or crystallization (see Non-Patent Documents 1 to 3).
The crystal structure usually adopts a spiral conformation that is loosely wound at about 18/1, and the interior of the spiral has a space measuring about 1 nm in diameter, in which space solvent molecules are included.
The inventors of the present invention have already completed an invention relating to a fullerene-macromolecule complex in which fullerene is included inside the spiral conformation of a syndiotactic polymethacrylate-type or syndiotactic polyacrylate-type polymer, and a process for producing the same, and filed a patent application thereon (see Patent Document 1).
Examples reported hitherto to control the direction of spiral winding using a general-purpose polymer, are limited to polymethacrylate-type or polyacrylate-type isotactic polymers, and are also limited to macromolecules having a structure with bulky side chains.
The direction of winding of a resulting spiral polymer was determined by the chiral initiator or auxiliary agent used in the polymerization reaction, and the polymer had a static spiral structure that could not be altered thereafter (Non-Patent Document 4).
As a methacrylic acid ester polymer having such a unidirectionally wound spiral structure, isotactic poly(triphenylmethyl methacrylate) is well known (for example, Non-Patent Document 5).
This unidirectionally wound polymer has been put to practical use in columns for separation of chiral compounds.
However, such a polymer has a disadvantage that the bulky tertiary ester group is prone to undergo hydrolysis and easily changes to carboxylic acid, and as a result, the spiral structure is readily destroyed (Non-Patent Document 6).
Furthermore, since the raw material is a special ester called triphenylmethyl ester and is not a general-purpose monomer, there is another disadvantage that the synthesis processes are complicated, and the production cost goes up.
This has been a significant problem in the practical use of the polymer.
Patent Document 1: Japanese Patent Application No. 2006-238368
Non-Patent Document 1: Kusuyama, H.; Takase, M.; Higashihata, Y.; Tseng, H.; Chatani, Y.; Tadokoro, H. Polymer, 1982, 23, 1256.
Non-Patent Document 2: Kusuyama, H.; Miyamoto, N.; Chatani, Y.; Tadokoro, H. Polymer 1983, 24, 119.
Non-Patent Document 3: Berghmans, M.; Thihs, S.; Cornette, M.; Berghmans, H.; Schryver, F. C. Macromolecules 1994, 27, 7669.
Non-Patent Document 4: Nakano, T.; Okamoto, Y. Chem. Rev. 2001, 101, 4013.
Non-Patent Document 5: Okamoto, Y.; Suzuki, K.; Ohta, K.; Hatada, K.; Yuki, H. J. Am. Chem. Soc. 1979, 101, 4763.
Non-Patent Document 6: Okamoto, Y.; Yashima, E.; Ishikura, M.; Hatada, K. Polym. J. 1987, 19, 1183.
Non-Patent Document 7: Spevacek, J.; Schneider, B. Adv. Colloid Interface Sci. 1987, 27, 81.
Non-Patent Document 8: Yoshida, Z.; Takekuma, H.; Takekuma, S.; Matsubara, Y. Angew. Chem. Int. Ed. Engl. 1994, 33, 1597.

特許請求の範囲(英語) [claim1]
1. A syndiotactic polymethacrylate or syndiotactic polyacrylate spiral macromolecular compound that is controlled in the direction of winding of the spiral structure, wherein a syndiotactic triad content (rr content) is 80% or more.
[claim2]
2. The spiral macromolecular compound according to claim 1, wherein the syndiotactic polymethacrylate polymer is syndiotactic polymethyl methacrylate.
[claim3]
3. The spiral macromolecular compound according to claim 1 produced by the process comprising: dissolving in a solvent a syndiotactic polymethacrylate or syndiotactic polyacrylate polymer of which a syndiotactic triad content (rr content) is 80% or more and a chiral compound in an amount 10% or more by volume with respect to said solvent; and
subsequently subjecting the obtained solution to cooling or concentration to form a solid matter.
[claim4]
4. The spiral macromolecular compound according to claim 1, wherein absorption circular dichroism is observed by measuring the circular dichroism (CD).
[claim5]
5. The spiral macromolecular compound according to claim 1 having unidirectionally wound spiral structure wherein direction of winding is controlled in either clockwise or counterclockwise.
[claim6]
6. The spiral macromolecular compound according to claim 5, wherein the syndiotactic polymethacrylate polymer is syndiotactic polymethyl methacrylate (st-PMMA).
  • 発明者/出願人(英語)
  • KAWAUCHI TAKEHIRO
  • KUMAKI JIRO
  • YASHIMA EIJI
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
米国特許分類/主・副
  • 524/495
  • 524/523
参考情報 (研究プロジェクト等) ERATO YASHIMA Super-structured Helix AREA
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