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EP-3476858-B1 - METAL COMPLEX AND METHOD FOR PRODUCING THE SAME, CATALYST COMPONENT FOR OLEFIN POLYMERIZATION AND CATALYST FOR OLEFIN POLYMERIZATION CONTAINING THE METAL COMPLEX, AND METHODS FOR PRODUCING ALPHA-OLEFIN POLYMER AND COPOLYMER USING THE CATALYST FOR OLEFIN POLYMERIZATION

EP3476858B1EP 3476858 B1EP3476858 B1EP 3476858B1EP-3476858-B1

Inventors

  • NOZAKI, KYOKO
  • ITO, SHINGO
  • TAO, Wen-jie
  • KONISHI, Yohei
  • OHTAKI, HISASHI
  • OISHI, YASUO
  • TANNA, AKIO
  • TAYANO, TAKAO

Dates

Publication Date
20260506
Application Date
20170726

Claims (9)

  1. A metal complex obtained by contacting a compound represented by the following general formula [I] or [II] with a transition metal compound containing nickel or palladium as a transition metal belonging to 9th, 10th or 11th group in the periodic table: wherein R 1 to R 6 , E 1 and X 1 in the general formulae [I] and [II] are as follows: R 1 , R 2 , R 3 and R 4 each independently represent an atom or group selected from the group consisting of the following (i) to (iv): (i) hydrogen, (ii) a halogen, (iii) a linear alkyl group having 1 to 30 carbon atoms, a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms and optionally having a side chain, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an alkylaryl group having 7 to 30 carbon atoms, each of the groups optionally having one selected from the group consisting of a heteroatom and a group containing a heteroatom, and (iv) OR 9 , CO 2 R 9 , CO 2 M', C(O)N(R 8 ) 2 , C(O)R 9 , SR 9 , SO 2 R 9 , SOR 9 , OSO 2 R 9 , P(O)(OR 9 ) 2-y (R 8 ) y , CN, NHR 9 , N(R 9 ) 2 , Si(OR 8 ) 3-x (R 8 ) x , OSi(OR 8 ) 3-x (R 8 ) x , NO 2 , SO 3 M', PO 3 M' 2 , P(O)(OR 9 ) 2 M' or an epoxy-containing group, where R 8 represents hydrogen or a hydrocarbon group having 1 to 20 carbon atoms; R 9 represents a hydrocarbon group having 1 to 20 carbon atoms; M' represents an alkali metal, an alkaline earth metal, ammonium, quaternary ammonium or phosphonium; x represents an integer of from 0 to 3; and y represents an integer of from 0 to 2; a plurality of groups appropriately selected from R 1 , R 2 , R 3 and R 4 optionally bind to each other to form an alicyclic ring, an aromatic ring, or a heterocyclic ring containing a heteroatom selected from the group consisting of oxygen, nitrogen and sulfur, and in this case, a number of ring members is 5 to 8, and the ring optionally has a substituent group thereon; R 5 and R 6 each independently represent 1-adamantyl group, 5-methyl-2-(propan-2-yl)cyclohexyl group, 2,6-dimethylheptan-4-yl group, 2,4-dimethylpentan-3-yl group, bicyclo-[2.2.1]-hept-2-yl group, 2,4-phenylpentan-3-yl group, cycloheptyl group or 2-heptyl group; E 1 represents phosphorus; and X 1 represents oxygen, and wherein, in the general formula [I], Z represents hydrogen atom, R 9 SO 2 group where R 9 is as aforementioned or CF 3 SO 2 group, and m represents a valence of Z.
  2. The metal complex according to Claim 1, having a structure represented by the following general formula [III]: wherein R 1 to R 7 , E 1 , X 1 , M and L 1 in the general formula [III] are as follows: R 1 to R 6 , E 1 and X 1 are the same as in the general formulae [I] and [II]; M represents nickel or palladium as the transition metal belonging to 9th, 10th or 11th group in the periodic table; R 7 represents hydrogen or a hydrocarbon group having 1 to 20 carbon atoms and optionally having one selected from the group consisting of a heteroatom and a group containing a heteroatom; L 1 represents a ligand coordinated to M; and R 7 and L 1 optionally bind to each other to form a ring.
  3. The metal complex according to Claim 1 or 2, wherein R 3 is hydrogen.
  4. A method for producing the metal complex according to Claim 2 or 3, the metal complex having the structure represented by the general formula [III], wherein the compound represented by the general formula [I] or [II] is contacted with the transition metal compound containing nickel or palladium as the transition metal belonging to 9th, 10th or 11th group in the periodic table.
  5. A catalyst component for olefin polymerization, comprising the metal complex defined by any one of Claims 1 to 3 or a metal complex obtained by the production method defined by Claim 4.
  6. A catalyst for olefin polymerization, comprising the following components (A) and (B), and optionally further comprising the following component (C): the component (A): the metal complex defined by any one of Claims 1 to 3 or a metal complex obtained by the production method defined by Claim 4 the component (B): a compound reactive with the component (A) to form an ion pair, or an ion-exchange layered silicate the component (C): an organoaluminum compound.
  7. The catalyst for olefin polymerization according to Claim 6, wherein the component (B) is aluminoxane.
  8. A method for producing an α-olefin polymer, wherein (a) an α-olefin is polymerized or copolymerized in the presence of the catalyst for polymerization defined by Claim 6 or 7.
  9. A method for producing an α-olefin copolymer, wherein (a) an α-olefin and (b) a (meth)acrylic acid ester monomer, vinyl monomer or allyl monomer are copolymerized in the presence of the catalyst for polymerization defined by Claim 6 or 7.

Description

Technical Field The present invention relates to a metal complex useful for producing an α-olefin polymer and an α-olefin copolymer, a method for producing the metal complex, a catalyst component and a catalyst for olefin polymerization, and methods for producing an α-olefin polymer and an α-olefin copolymer using the same. Background Art A copolymer of α-olefin and a polar group-containing monomer is an industrially useful polymer. To obtain the copolymer by direct polymerization, a high pressure radical method is generally employed. However, this method has a disadvantage in that it is not possible to polymerize higher α-olefins such as propylene. It is industrially difficult to produce the copolymer by methods other than the high pressure radical method, and catalyst deactivation is inevitable in the case of using a Ziegler catalyst or metallocene catalyst. Then, in the field of metallocene catalysts, copolymerization of ethylene and methyl methacrylate was enabled by an organic rare earth metal complex-based metallocene catalyst. Since the 1990s, copolymerization of ethylene and a polar group-containing comonomer by a late transition metal complex catalyst, has been intensively studied. For example, (α-diimine)palladium complexes as reported by Brookhart, et al. and (salicyl amidinate)nickel catalysts as reported by Grubbs et al. are known. In the case of using those catalysts, low polymerization temperature is employed to suppress frequency of chain transfer; thereby, low copolymer productivity and low molecular weight are generally caused. In recent years, the problem with copolymerization of ethylene and a polar group-containing monomer was solved by findings such as (phosphorus sulfonate)palladium complexes (see Patent Literature 1) and (phosphorus phenolate)nickel complexes (see Patent Literatures 2 to 4, and Non-Patent Literatures 1 and 2), which are so-called SHOP-based catalysts. Further, Patent Literature 5 describes the preparation of an α-olefin-(meth)acrylic acid ester copolymer as well as an α-olefin-(meth)acrylic acid ester copolymer. As just described, the (phosphorus phenolate)nickel complexes are effective as a copolymerization catalyst for copolymerization of ethylene and a polar group-containing monomer. However, there has been no report of the effectiveness of the (phosphorus phenolate)nickel complexes in copolymerization of α-olefin and a polar group-containing monomer. Citation List Patent Literatures Patent Literature 1: JP 2010-150246 APatent Literature 2: WO 2010/050256 A1Patent Literature 3: US 6,559,326 B1Patent Literature 4: JP 2005-307021 APatent Literature 5: JP 2009-132898 A Non-Patent Literatures Non-Patent Literature 1: J. Heinicke et al., "Chem. Eur. J.", 2003, 9, 6093.Non-Patent Literature 2: J. Heinicke et al., "European Journal of Inorganic Chemistry", 2000, 3, 431. Summary of Invention Technical Problem In light of the problems of the prior art, an object of the present invention is to provide a novel catalyst component with excellent polymerization activity, which is used for producing an α-olefin polymer and α-olefin copolymer, especially used for producing a high-molecular-weight polymer, and methods for producing an α-olefin polymer and an α-olefin copolymer using the same. Solution to Problem To achieve the above object, the inventors of the present invention conducted research and found a novel transition metal complex having a phosphorus phenolate ligand structure, which differs from existing (phosphorus phenolate) transition metal complexes, and they found that homopolymerization of α-olefin or copolymerization with a polar group-containing monomer is possible. Also, they found that a (co)polymer with a higher molecular weight can be obtained, and they accomplished the present invention which is set out in the appended claims. Advantageous Effects of Invention By the present invention, an α-olefin homopolymer with a higher molecular weight can be obtained by higher polymerization activity than ever before; moreover, copolymerization of α-olefin and a polar group-containing monomer by excellent polymerization activity, can be achieved. Brief Description of Drawing FIG. 1 is an ORTEP diagram of complex (B-350)NiPh(PEt3). Description of Embodiments According to the present invention, there are provided a metal complex as a reaction product obtainable by contacting a compound represented by a general formula [I] or [II] with a transition metal compound containing nickel or palladium as a transition metal belonging to 9th, 10th or 11th group in the periodic table, that is, a metal complex represented by a general formula [III] (hereinafter may be referred to as metal complex [III]), and also provided a method using the metal complex as a catalyst component, that is, a method for producing a polymer or copolymer of (a) α-olefin and a method for producing a copolymer of (a) α-olefin and (b) (meth)acrylic acid ester monomer, vinyl monomer or allyl monomer, both in t