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(12) Patent Application Publication (10) Pub. No.: US 2010/0256329 A1 Nozaki Et Al US 2010O256329A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0256329 A1 Nozaki et al. (43) Pub. Date: Oct. 7, 2010 (54) STEREOSELECTIVE ALTERNATING Publication Classification COPOLYMERIZATION OF EPOXDE WITH (51) Int. Cl. CARBON DOXDE C08G 64/00 (2006.01) C07D 207/04 (2006.01) (75) Inventors: Kyoko Nozaki, Tokyo (JP); Koji (52) U.S. Cl. ......................................... 528/405; 548/403 Nakano, Tokyo (JP) (57) ABSTRACT Correspondence Address: The present invention provides a method for manufacturing MERCHANT & GOULD PC polycarbonate, which has a high conversion rate of a propy P.O. BOX 2903 lene oxide material into a polymer and can control stereo MINNEAPOLIS, MN 55402-0903 (US) regularity of the macromolecular structure, and a catalytic compound for the manufacturing method. (73) Assignee: The University of Tokyo, The manufacturing method of the present invention is a Bunkyo-ku, Tokyo (JP) method for manufacturing a polycarbonate copolymer by copolymerizing an epoxide compound as a monomer with (21) Appl. No.: 12/663,639 carbon dioxide in the presence of a planar tetracoordinate type cobalt-Schiff base complex, wherein a ligand of the Schiff base is N,N'-bis(2-hydroxybenzylidene)ethylenedi (22) PCT Fled: Jun. 6, 2008 amine, N,N'-bis(2-hydroxybenzylidene)phenylenediamine, or a derivative thereof, and a methyl group substituted with an (86) PCT NO.: PCT/UP2008/060813 amino group having an asymmetrical carbon atom or an asymmetrical axis is introduced to the 3- and/or 3'-position of S371 (c)(1), the benzene ring derived from the salicyl group. In addition, (2), (4) Date: Jun. 15, 2010 the catalytic compound of the present invention is a cobalt Schiffbase complex, wherein a methyl group substituted with (30) Foreign Application Priority Data an amino group having an asymmetrical carbon atom or an asymmetrical axis is introduced to the 3- and/or 3'-position of Jun. 8, 2007 (JP) ................................. 2007-153322 the salicyl group. US 2010/0256329 A1 Oct. 7, 2010 STEREOSELECTIVE ALTERNATING COPOLYMERIZATION OF EPOXDE WITH OAc CARBON DOXDE TECHNICAL FIELD / 0001. The present invention relates to a method for manu =N e/ o facturing polycarbonate by alternating copolymerization of CO epoxide and carbon dioxide, and a catalyst used for the manu Bu / Y. Bu facturing method. In particular, the present invention relates AcO to a method for manufacturing polycarbonate having a high Stereoregularity and a catalyst used for the manufacturing method. BACKGROUND ART 0007 As a method for utilizing the above compound 0002 Recently, as a technology for efficient use of carbon which attain such a high Substrate conversion, they reported a dioxide, a method for manufacturing polycarbonate by copo method wherein, after all the first epoxy material (propylene lymerization of epoxide with carbon dioxide has been receiv oxide) is converted to a copolymer, the second epoxy material ing attention. In addition, researchand development aiming at (1-butene oxide) is further added to form a different polymer novel properties and functions, and expansion ofuses thereof, chain at the end of the first polymer chain, and thereby a block by controlling the stereoregularity of polycarbonate, are copolymer is manufactured. being carried out. DISCLOSURE OF THE INVENTION 0003 For example, control of stereoregularity by regu larly introducing an optically-active center in the main chain 0008. However, in the synthesis of a polycarbonate of polycarbonate is being investigated. An optically active copolymer, a catalyst which has Superior enantioselectivity and yet shows a high Substrate conversion has not been polycarbonate, which is obtained by alternating copolymer reported. Therefore, in order to further expand the possibility ization of one of the enantiomers of chiral epoxide with of controlling the stereoregularity of polycarbonate copoly carbon dioxide, has a main-chain structure with very high mers and realize a variety of Stereosequence of polycarbon Stereoregularity, and is predicted to display Superior mechani ate, the development of Such a catalytic compound is a new cal and physico-chemical properties, and therefore applica challenge. tion of a separation medium for chromatography and separa 0009. The present invention provides a method for manu tion membrane, a biodegradable material, a ferroelectric facturing a polycarbonate copolymer by copolymerizing an material, and a piezoelectric pyroelectric material is envi epoxide compound as a monomer with carbon dioxide in the Sioned. presence of a planar tetracoordinate-type cobalt-Schiff base complex, wherein a ligand of the Schiff base is N,N'-bis(2- 0004 While the above optically active polycarbonate hydroxybenzylidene)ethylenediamine (salen), N,N'-bis(2- could be manufactured by using one of the enantiomers of a hydroxybenzylidene)phenylenediamine (salph) or a deriva chiral epoxide, a chiral epoxide is usually obtained as a race tive thereof, and a methyl group Substituted with an amino mic mixture, and hence in the above manufacturing method, group having an asymmetrical carbonatom or an asymmetri an enantiomerically pure epoxide has to be prepared, which is cal axis, is introduced to the 3- and/or 3'-position of the very expensive. On the other hand, an optically active poly benzene ring derived from the salicyl group. carbonate can be synthesized through enantioselective alter 0010. In addition, another aspect of the present invention provides a cobalt-Schiff base complex usable as a polymer nating copolymerization with carbon dioxide, where one of ization catalyst for manufacturing polycarbonate, wherein a the enantiomers of a racemic epoxide is selectively copoly methyl group Substituted with an amino group having an merized. Therefore, studies aiming at the development of an asymmetrical carbon atom or an asymmetrical axis is intro enantioselective alternating copolymerization reaction using duced to the 3- and/or 3'-position of the salicyl group. a racemic mixture of epoxide are being carried out. 0011. The cobalt complex compound of the present inven 0005 X. Lu, et al. reported that they attempted an alter tion attain a high enantioselectivity when using a racemic nating copolymerization reaction of a racemic mixture of mixture of epoxide. Therefore, a variety of polycarbonate epoxide with carbon dioxide, using a binary catalyst of a copolymers with a controlled Stereoregularity can be manu Schiff base-cobalt complex in combination with a nucleo factured from the racemic mixture of epoxide and carbon philic reagent to obtain optically active polycarbonate (J. Am. dioxide. Chem. Soc., 2006, 128, 1664-1674). BEST MODE FOR CARRYING OUT THE 0006 K. Nakano, et al. discovered that, in the case when INVENTION the following compound belonging to the Schiffbase-cobalt 0012. The cobalt complex used as a catalyst in the present complex was used by itself, it could suppress the formation of invention comprises a Schiffbase that is a planartetra-dentate by-product, cyclic carbonate, and the conversion of the pro ligand. The typical Schiffbase ligand is a salen ligand (N,N'- pylene oxide to polycarbonate was about 80%, although the bis(salicylidene)ethylenediamine) and a derivative thereof enantioselectivity was not observed (Angew. Chem. Int. Ed, (hereinafter, referred to as a “salen-type ligand'). The salen 2006, 45,7274-7277). type ligand is obtained by a dehydration condensation reac US 2010/0256329 A1 Oct. 7, 2010 tion of Salicylaldehyde and ethylenediamine, and by using another diamine instead of ethylenediamine or by introducing -continued a Substituent in the aromatic ring part of Salicylic acid, a NR: variety of derivatives can be obtained. Specifically preferable compounds among Such derivatives are the Salcy ligand (N,N'-bis(salicylidene)-1,2-cyclohexanediamine) which is obtained by modifying the ethylenediamine part of the salen O ligand to cyclohexanediamine and a derivative thereof, or the salph ligand (N.N'-bis(salicylidene)-phenylenediamine), in MeO| Ph MeO which the ethylenediamine part is replaced by phenylenedi Ph amine, and a derivative thereof. 0013. A methyl group substituted with an amino group having an asymmetrical carbon center or an asymmetrical 0017 wherein, axis (hereinafter, referred to as an 'arm') can be introduced to 0018 X represents any one group or atom selected from the 3- and/or 3'-position of the Salicyl group contained in the group consisting of H. C.20 alkyl, C-2 alkoxy, C-2 these salen-type ligands. In the case when the arms are intro aryl, F, Cl, Br, and I, and Y represents an anionic ligand duced into both 3- and 3'-positions, the two substituents may selected from the group consisting of aliphatic carboxylate, be the same or different. The amino group constituting the aromatic carboxylate, Cl, Br, and I. arm may be a tertiary amino group, preferably is a pyrrolidi 0019. A specifically preferable cobalt-Schiff base com nyl group or a piperidinyl group, and most preferably is a plex of the present invention is the compound represented by pyrrolidinyl group. Thus, for example, in the case when the the following formula. amino group constituting the arm is a pyrrolidinyl group with a single Substituent, the carbon of the 5-membered ring to which the substituent is bound is the asymmetrical center, showing optical activity. Below, specific examples of the arm N are shown (Note: they are not limited to the following sub O stituents). / N / o N e/ o MeO Ph MeO Ph Bu O/"\, Bu O 0014. The absolute configuration around the asymmetri cal carbon center or the asymmetrical axis defining the con figuration of the amino group constituting the arm is either 1s. (R) or (S). The absolute configuration of the arm can be RN NHR selected and introduced depending on the absolute configu NR : ration of a polycarbonate having the desired optical activity. 0015 The central metal of the above cobalt complex is involved in the polymerization reaction of the present inven O tion, and so one or two reactive ligands can coordinate along t N the axial directions of the central metal so that the cobalt MeO Ph metal can easily react with the substrate.
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