Polar group-containing olefin copolymer and method for producing the same

Abstract

To provide a novel polar-group-containing olefin copolymer where a lactone structure is introduced in a side chain.SOLUTION: The polar-group-containing olefin copolymer comprises: a structural unit (A) which is derived from at least one monomer selected from the group consisting of ethylene and olefins having 3 to 20 carbon atoms; and at least one structural unit (B) which is selected from the group consisting of structural units represented by the general formula (I) in the figure and structural units represented by general formula (II) in the figure.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to a novel polar group-containing olefin copolymer and a method for producing the same, and more particularly to a novel polar group-containing olefin copolymer having a lactone structure introduced into the side chain, and a method for producing the same. [Background technology]

[0002] Olefin polymers, such as ethylene polymers and copolymers of ethylene and α-olefins, are excellent among resin materials in terms of physical properties and moldability, and are also highly economical and environmentally friendly. Therefore, olefin polymers are very widely used and important industrial materials. However, since olefin polymers do not have polar groups, it has been difficult to apply them to applications requiring physical properties such as adhesion to other materials, printability, or compatibility with fillers.

[0003] In recent years, there has been an increasing need for polar group-containing olefin copolymers in which polar groups have been introduced into polyolefins, and various examples of such copolymers have been reported. Known polar group-containing olefin copolymers include copolymers having polar groups in their side chains, such as copolymers having carbonyl groups in their side chains obtained by copolymerizing ethylene with acrylic acid esters or vinyl ketones (see, for example, Patent Document 1).

[0004] On the other hand, carbon dioxide is an inexpensive and easily available carbon source, and its effective use is desirable. Patent Document 2 discloses, as an example of using carbon dioxide in a polymer material, a homopolymer obtained by radical polymerization of a lactone monomer produced from carbon dioxide and a 1,3-dienes. Furthermore, Patent Document 3 discloses a methacrylate ester copolymer obtained by radical copolymerization of the lactone monomer and a methacrylate ester monomer. It is described that the methacrylate ester copolymer has a lactone ring in the main chain skeleton. Patent Document 3 aims to provide a resin material with improved heat resistance without impairing the optical transparency and processability of polymethacrylate ester resins. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Patent No. 6309206 [Patent Document 2] Japanese Patent Application Laid-Open No. 2014-240476 [Patent Document 3] Japanese Patent Application Publication No. 2018-168301 Summary of the Invention [Problem to be solved by the invention]

[0006] Patent Documents 2 and 3 do not describe at all the copolymerization of the lactone monomer with an olefin monomer, which is a non-polar monomer. An object of the present disclosure is to provide a novel polar group-containing olefin copolymer in which a lactone structure is introduced into a side chain of the polymer chain in order to enhance the functionality of the olefin polymer. [Means for solving the problem]

[0007] The present disclosure relates to the following [1] to [6]. [1] A structural unit (A) derived from at least one monomer selected from the group consisting of ethylene and olefins having 3 to 20 carbon atoms; At least one structural unit (B) selected from the group consisting of structural units represented by the following general formula (I) and structural units represented by the following general formula (II), A polar group-containing olefin copolymer comprising:

[0008] [ka] [In general formula (I), R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R 7 , R 8 and R 9 are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1, or 2. When n=0, adjacent carbon atoms are directly bonded to each other, and R 3 and R 4 does not exist.]

[0009] [ka] [In general formula (II), R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R 17 , R 18 and R 19 are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1, or 2. When n=0, adjacent carbon atoms are directly bonded to each other, and R 13 and R 14 does not exist.]

[0010] [2] The polar group-containing olefin copolymer according to [1], characterized in that the ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) determined by gel permeation chromatography (GPC) is in the range of 1.5 to 5.0.

[0011] [3] The structural unit (A) is derived from ethylene, and 13 The polar group-containing olefin copolymer according to [1] or [2] above, characterized in that the degree of methyl branching calculated by C-NMR is 20.0 or less per 1,000 carbon atoms.

[0012] [4] A method for producing the polar group-containing olefin copolymer according to any one of [1] to [3] above, characterized in that the polar group-containing olefin copolymer is produced in the presence of a transition metal catalyst of Groups 4 to 10 of the periodic table. [5] The method for producing a polar group-containing olefin copolymer according to [4], wherein the transition metal catalyst is a transition metal catalyst in which a chelating phosphine compound or a chelating carbene compound is coordinated to nickel or palladium metal.

[0013] [6] In the presence of a catalyst containing a transition metal from Groups 4 to 10 of the periodic table, A method for producing a polar group-containing olefin copolymer, characterized by polymerizing the following monomer (A) and the following monomer (B): Monomer (A): At least one selected from the group consisting of ethylene and olefins having 3 to 20 carbon atoms Monomer (B): At least one selected from the group consisting of lactone monomers represented by the following general formula (1) and lactone monomers represented by the following general formula (2):

[0014] [ka] [In general formula (1), R 1 , R 2 , R3 , R 4 , R 5 and R 6 are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R 7 , R 8 and R 9 are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1, or 2. When n=0, adjacent carbon atoms are directly bonded to each other, and R 3 and R 4 does not exist.]

[0015] [ka] [In general formula (2), R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R 17 , R 18 and R 19 are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1, or 2. When n=0, adjacent carbon atoms are directly bonded to each other, and R 13 and R 14 does not exist.] [Effects of the Invention]

[0016] According to the present disclosure, it is possible to provide a novel polar group-containing olefin copolymer in which a lactone structure is introduced into a side chain of the polymer chain. [Brief explanation of the drawings]

[0017] [Figure 1] FIG. 1 shows the results of 1H-NMR measurement of polar group-containing olefin copolymer 8 of Example 8. [Figure 2]FIG. 2 shows the results of 1H-NMR measurement of polar group-containing olefin copolymer 11 of Example 11. [Figure 3] FIG. 3 shows the results of 13C-NMR measurement of polar group-containing olefin copolymer 12 of Example 12. DETAILED DESCRIPTION OF THE INVENTION

[0018] The polar group-containing olefin copolymer of the present disclosure will be described in detail below for each item. In this specification, the term "(meth)acrylic" refers to both acrylic and methacrylic. In addition, in this specification, the use of "to" to indicate a range of values ​​means that the values ​​before and after it are included as the lower limit and upper limit. Furthermore, in the prefixes for structural isomers of alkyl groups, "i" stands for iso, "n" stands for normal, "s" stands for secondary, and "t" stands for tertiary. When no prefix for structural isomers is given to an alkyl group, it indicates a normal structure.

[0019] 1. Polar group-containing olefin copolymer The polar group-containing olefin copolymer of the present disclosure comprises a structural unit (A) derived from at least one monomer selected from the group consisting of ethylene and olefins having 3 to 20 carbon atoms, At least one structural unit (B) selected from the group consisting of structural units represented by the following general formula (I) and structural units represented by the following general formula (II), The present invention is characterized by comprising:

[0020] [ka] [In general formula (I), R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R 7 , R 8 and R 9 are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1, or 2. When n=0, adjacent carbon atoms are directly bonded to each other, and R 3 and R 4 does not exist.]

[0021] [ka] [In general formula (II), R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R 17 , R 18 and R 19 are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1, or 2. When n=0, adjacent carbon atoms are directly bonded to each other, and R 13 and R 14 does not exist.]

[0022] The polar group-containing olefin copolymer of the present disclosure is a novel polar group-containing olefin copolymer in which a lactone structure is introduced into a side chain of the polymer chain, and contributes to improving the functionality of olefin-based polymers.

[0023] The polar group-containing olefin copolymer of the present disclosure can be easily produced by hydrolyzing the lactone structure of the introduced side chain, for example, as shown below.

[0024] [ka]

[0025] Furthermore, when the polar group-containing olefin copolymer of the present disclosure has a structural unit represented by the general formula (I), for example, it has an ethylenically unsaturated group in the side chain, so that it can be post-modified. An example of post-modification is crosslinking, and the polar group-containing olefin copolymer of the present disclosure is also promising as a macromonomer. When the polar group-containing olefin copolymer of the present disclosure has a structural unit represented by the general formula (I), for example, it has an enone structure in the side chain, and therefore can be used as a substrate for, for example, a Michael addition reaction. As described above, the polar group-containing olefin copolymer of the present disclosure is expected to be a raw material that can be converted into a variety of composite materials.

[0026] Furthermore, since the 6-membered lactone monomer having an ethylenically unsaturated group that derives the structural unit (B) can also be derived from carbon dioxide, the polar group-containing olefin copolymer of the present disclosure has new added value as a carbon recycled resin.

[0027] (1) Structural unit (A) The structural unit (A) is a structural unit derived from at least one monomer (A) selected from the group consisting of ethylene and olefins having 3 to 20 carbon atoms. The monomer (A) used in the present disclosure is at least one selected from the group consisting of ethylene and olefins having 3 to 20 carbon atoms. The olefins having 3 to 20 carbon atoms may be linear olefins or cyclic olefins, and examples thereof include at least one selected from the group consisting of α-olefins having 3 to 20 carbon atoms and cyclic olefins having 4 to 20 carbon atoms. The α-olefin having 3 to 20 carbon atoms used in the present disclosure has the structural formula: CH═CHR 20 α-olefins (R 20 is a hydrocarbon group having 1 to 18 carbon atoms, which may have a linear structure or may be branched), and more preferably an α-olefin having 3 to 12 carbon atoms. Examples of cyclic olefins having 4 to 20 carbon atoms include cyclobutene, cyclopentene, cyclohexene, and norbornene.

[0028] Specific examples of the monomer (A) include ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-octene, 1-decene, 3-methyl-1-butene, 4-methyl-1-pentene, and norbornene. From the viewpoint of polymer production efficiency, the monomer (A) is preferably at least one selected from the group consisting of ethylene, propylene, 1-butene, and norbornene, and more preferably ethylene or propylene. The structural unit (A) may be of one type alone or of two or more types.

[0029] Examples of combinations of the two include structural units derived from ethylene-propylene, ethylene-1-butene, ethylene-1-hexene, ethylene-1-octene, propylene-1-butene, propylene-1-hexene, propylene-1-octene, and ethylene-norbornene. Examples of combinations of the three include structural units derived from ethylene-propylene-1-butene, ethylene-propylene-1-hexene, ethylene-propylene-1-octene, propylene-1-butene-hexene, and propylene-1-butene-1-octene.

[0030] In the present disclosure, the monomer (A) used in the structural unit (A) preferably contains at least one of ethylene and propylene, more preferably contains ethylene or propylene, and may further contain at least one α-olefin having 3 to 20 carbon atoms, as needed. The amount of ethylene in the monomer (A) may be 65 mol % to 100 mol %, 70 mol % to 100 mol %, or 90 mol % to 100 mol %, relative to 100 mol % of the total amount of the monomer (A). The amount of propylene in the monomer (A) may be 65 mol % to 100 mol %, 70 mol % to 100 mol %, or 90 mol % to 100 mol % relative to 100 mol % of the total amount of the monomer (A).

[0031] (2) Structural unit (B) The structural unit (B) is at least one structural unit selected from the group consisting of structural units represented by the following general formula (I) and structural units represented by the following general formula (II).

[0032] [ka] [In general formula (I), R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R 7 , R 8 and R 9 are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1, or 2. When n=0, adjacent carbon atoms are directly bonded to each other, and R 3 and R 4 does not exist.]

[0033] [ka] [In general formula (II), R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R 17 , R 18 and R 19are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1, or 2. When n=0, adjacent carbon atoms are directly bonded to each other, and R 13 and R 14 does not exist.]

[0034] In general formulas (I) and (II), examples of the hydrocarbon group having 1 to 30 carbon atoms that may have a substituent include linear, branched, and cyclic saturated or unsaturated aliphatic hydrocarbon groups, aromatic hydrocarbon groups, and combinations thereof. Examples of the hydrocarbon group having 1 to 30 carbon atoms include the following examples of alkyl groups having 1 to 30 carbon atoms, as well as alkenyl groups such as ethenyl, propenyl, butenyl, and pentenyl, aryl groups such as phenyl, methylphenyl, n-propylphenyl, i-propylphenyl, n-butylphenyl, i-butylphenyl, s-butylphenyl, t-butylphenyl, n-hexylphenyl, trimethylphenyl, pentamethylphenyl, biphenyl, naphthyl, anthracenyl, fluorenyl, and tolyl, and aralkyl groups such as benzyl, phenylethyl, phenylpropyl, naphthylmethyl, diphenylmethyl, and triphenylmethyl.

[0035] The alkyl group having 1 to 30 carbon atoms may be, for example, linear, branched, or cyclic, and includes, for example, a methyl group, an ethyl group, a 1-propyl group, a 1-butyl group, a 1-pentyl group, a 1-hexyl group, a 1-heptyl group, a 1-octyl group, a 1-nonyl group, a 1-decyl group, a t-butyl group, a tricyclohexylmethyl group, an isopropyl group, a 1-dimethylpropyl group, a 1,1,2-trimethylpropyl group, a 1,1-diethylpropyl group, an isobutyl group, a 1,1-dimethylbutyl group, a 2-pentyl group, a 2-pentyl Examples of such groups include a 3-pentyl group, a 2-hexyl group, a 3-hexyl group, a 2-ethylhexyl group, a 2-heptyl group, a 3-heptyl group, a 4-heptyl group, a 2-propylheptyl group, a 2-octyl group, a 3-nonyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a methylcyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclododecyl group, a 1-adamantyl group, a 2-adamantyl group, and a norbornyl group.

[0036] The hydrocarbon group having 1 to 30 carbon atoms may be a hydrocarbon group having 1 to 10 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, or a hydrocarbon group having 1 to 3 carbon atoms. The hydrocarbon group having 1 to 3 carbon atoms may be a methyl group, an ethyl group, a 1-propyl group, or an isopropyl group, and may be a methyl group or an ethyl group, or may be a methyl group.

[0037] The hydrocarbon group having 1 to 30 carbon atoms which may have a substituent includes a hydrocarbon group having 1 to 30 carbon atoms which has a substituent and a hydrocarbon group having 1 to 30 carbon atoms which has no substituent. When the hydrocarbon group has a substituent, examples of the substituent include a halogen atom, a hydroxyl group, a formyl group, an epoxy group, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an amino group which may be substituted with a hydrocarbon group having 1 to 30 carbon atoms, an acyloxy group having 1 to 30 carbon atoms, an acyl group having 1 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, an aryloxycarbonyl group having 6 to 30 carbon atoms, etc. The number of carbon atoms contained in the substituent is not included in the number of carbon atoms of the hydrocarbon group.

[0038] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0039] In addition, the alkoxy group having 1 to 30 carbon atoms is -OR a where R a represents an alkyl group having 1 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms. The lower limit of the number of carbon atoms in the alkoxy group may be 1 or more, or may be 2 or more, and the upper limit may be 30 or less, or may be 20 or less, or may be 10 or less. R a The alkyl group having 1 to 30 carbon atoms and the aralkyl group having 7 to 30 carbon atoms in the above formula can be those corresponding to the alkyl group having 1 to 30 carbon atoms and the aralkyl group having 7 to 30 carbon atoms, among the hydrocarbon groups having 1 to 30 carbon atoms.

[0040] Suitable specific examples of the alkoxy group having 1 to 30 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, an n-pentoxy group, an n-hexyloxy group, a cyclopropoxy group, a cyclopentoxy group, a cyclohexyloxy group, an n-octoxy group, an n-decyloxy group, and a benzyloxy group.

[0041] In addition, an aryloxy group having 6 to 30 carbon atoms is represented by -OR a’ where R a’ represents an aryl group having 6 to 30 carbon atoms. The lower limit of the number of carbon atoms in the aryl group may be 6 or more, or may be 8 or more, and the upper limit may be 30 or less, or may be 20 or less, or may be 12 or less. R a’ In the above, examples of the aryl group having 6 to 30 carbon atoms include those corresponding to the aryl group having 6 to 30 carbon atoms among the hydrocarbon groups having 1 to 30 carbon atoms.

[0042] Specific examples of the aryloxy group having 6 to 30 carbon atoms include a phenoxy group, a methylphenoxy group, an ethylphenoxy group, an n-butylphenoxy group, a naphthyloxy group, a fluorenyloxy group, and an anthracenyloxy group.

[0043] The amino group which may be substituted with a hydrocarbon group having 1 to 30 carbon atoms is represented by —N(R b )R c where R b and R c each independently represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms. The lower limit of the number of carbon atoms in the hydrocarbon group substituting the substituted amino group may be 1 or more, or may be 2 or more, and the upper limit may be 30 or less, or may be 20 or less, or may be 10 or less. R b and R c Examples of the hydrocarbon group having 1 to 30 carbon atoms in the formula (I) include the same hydrocarbon groups as those having 1 to 30 carbon atoms described above.

[0044] Suitable specific examples of the amino group which may be substituted with a hydrocarbon group having 1 to 30 carbon atoms include an amino group (-NH2), a monomethylamino group, a dimethylamino group, a monoethylamino group, a diethylamino group, a monoisopropylamino group, a diisopropylamino group, a monophenylamino group, and a diphenylamino group.

[0045] The acyloxy group having 1 to 30 carbon atoms is -OCOR d where R d represents a hydrocarbon group having 1 to 30 carbon atoms. The acyl group having 1 to 30 carbon atoms is —COR e where R e represents a hydrocarbon group having 1 to 30 carbon atoms. The alkoxycarbonyl group having 1 to 30 carbon atoms is -COOR f where R frepresents an alkyl group having 1 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms. An aryloxycarbonyl group having 6 to 30 carbon atoms is represented by -COOR f’ where R f’ represents an aryl group having 6 to 30 carbon atoms.

[0046] The number of carbon atoms in the acyloxy group, acyl group, alkoxycarbonyl group, and aryloxycarbonyl group does not include the number of carbon atoms in the carbonyl group. d , R e , R f , and R f’ The lower limit may be 1 or more, or may be 2 or more, and the upper limit may be 30 or less, or may be 20 or less, or may be 10 or less. Examples of the hydrocarbon group having 1 to 30 carbon atoms include the same hydrocarbon groups as those having 1 to 30 carbon atoms described above. f , and R f’ is R a , and R a’ It may be similar to:

[0047] Suitable specific examples of the acyloxy group having 1 to 30 carbon atoms include an acetyloxy group, a propionyloxy group, a (meth)acryloyloxy group, and a benzoyloxy group. Suitable specific examples of the acyl group having 1 to 30 carbon atoms include an acetyl group, a propionyl group, a (meth)acryloyl group, and a benzoyl group.

[0048] Suitable specific examples of the alkoxycarbonyl group having 1 to 30 carbon atoms include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonyl group, an n-butoxycarbonyl group, a t-butoxycarbonyl group, a cyclohexyloxycarbonyl group, a 2-ethylhexyloxycarbonyl group, and a benzyloxycarbonyl group. A specific example of the aryloxycarbonyl group having 6 to 30 carbon atoms is a phenoxycarbonyl group.

[0049] In the general formula (I) and the general formula (II), n is 0, 1 or 2. When n=0, adjacent carbon atoms are directly bonded to each other, and in general formula (I), R 3 and R 4 does not exist, and in general formula (II), R 13 and R 14 does not exist. When n=0, it is a five-membered lactone. When n=1, in general formula (I), C(R 3 )(R 4 ) is present, and in general formula (II), C(R 13 )(R 14 ) exists as a six-membered lactone. When n=2, in general formula (I), C(R 3 )(R 4 ) are present in two groups, and in general formula (II), C(R 13 )(R 14 ) exists in two forms and is a seven-membered lactone.

[0050] In general formula (I), R 1 , R 2 , R 3 , R 4 , R 5 and R 6 may each independently be a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, may be a hydrogen atom, a methyl group, or an ethyl group, or may be a hydrogen atom or a methyl group. In general formula (I), R 3 , R 4 , R 5 and R 6 may be a hydrogen atom, and R 1 and R 2 One of them may be a hydrogen atom and the other a methyl group. In addition, in the general formula (I), R 7 , R 8 and R 9 may each independently be a hydrogen atom, a methyl group, or an ethyl group, or may be a hydrogen atom or a methyl group. n is 0, 1 or 2, but may be n=1.

[0051] In general formula (II), R 11 , R 12 , R 13 , R 14 , R 15 and R 16 may be a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, may be a hydrogen atom, a methyl group or an ethyl group, or may be a hydrogen atom or a methyl group. In general formula (II), R 13 and R 14 may be a hydrogen atom, and R 15 and R 16 may each independently be a hydrogen atom or a methyl group, and R 11 and R 12 may each independently be a hydrogen atom or a methyl group, or both may be methyl groups. In addition, in the general formula (II), R 17 , R 18 and R 19 may each independently be a hydrogen atom, a methyl group, or an ethyl group, or may be a hydrogen atom or a methyl group. n is 0, 1 or 2, but may be n=1.

[0052] Examples of the structural unit (B) include, but are not limited to, the following structural units:

[0053] [ka]

[0054] Since the structural unit (B) has an ethylenically unsaturated group in the side chain and thus can be post-modified, the structural unit (B) may be at least one structural unit selected from the group consisting of structural units represented by general formula (I).

[0055] (3) Other structural units (C) The polar group-containing olefin copolymer of the present disclosure may further contain another structural unit (C) different from the structural unit (A) and the structural unit (B). The other structural unit (C) may be, for example, a structural unit derived from a monomer copolymerizable with the monomer (A) in the presence of a transition metal catalyst of Groups 4 to 10 of the periodic table, which will be described later. Examples of such monomer (C) include (meth)acrylic acid esters, (meth)acrylamides, (meth)acrylonitrile, vinylamides, vinyl acetate, allyl acetate, 3-butenyl acetate, 3-cyanopropene, methyl vinyl ether, 3-chloropropene, N-propylideneethenamine, 3-(methylthio)-1-propene, 3-(methylsulfinyl)-1-propene, 3-(methylsulfonyl)-1-propene, methyl 2-propene-1-sulfonate, dimethyl 2-propenylphosphonate, 5-methoxycarbonyl-2-norbornene, 2-norbornene-5-methanol, 9-epoxy-1-decene, vinylene carbonate, undecenoic acid esters, and undecenol. Specific examples of (meth)acrylic acid esters include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl (meth)acrylate, n-octyl (meth)acrylate, and 2-ethylhexyl (meth)acrylate, but are not limited to these. The polar group-containing olefin copolymer of the present disclosure may contain a structural unit derived from a lactone monomer different from the structural unit (B), but it need not contain any.

[0056] (4) Polar group-containing olefin copolymer The polar group-containing olefin copolymer of the present disclosure comprises a structural unit (A) derived from at least one monomer selected from the group consisting of ethylene and olefins having 3 to 20 carbon atoms, and at least one structural unit (B) selected from the group consisting of structural units represented by the general formula (I) and structural units represented by the general formula (II). The polar group-containing olefin copolymer of the present disclosure must contain at least one type of structural unit (A) and one type of structural unit (B), and must contain structural units derived from a total of two or more types of monomers.

[0057] In the present disclosure, the content of the structural unit (A) in the polar group-containing olefin copolymer may be appropriately selected depending on the desired physical properties. The content of the structural unit (A) in the polar group-containing olefin copolymer may, for example, have a lower limit of 80.00 mol% or more, 90.00 mol% or more, preferably 95.00 mol% or more, 97.00 mol% or more, or 99.00 mol% or more, relative to 100 mol% of all structural units. Meanwhile, the upper limit may be 99.99 mol% or less, 99.98 mol% or less, preferably 99.90 mol% or less, or 99.80 mol% or less. Any combination of the upper and lower limits may be used. Among these, the content of the structural unit (A) in the polar group-containing olefin copolymer may particularly preferably be 90.00 mol % to 99.98 mol %, 90.00 mol % to 99.90 mol %, or 90.00 mol % to 99.80 mol %, relative to 100 mol % of all structural units.

[0058] The content of the structural unit (B) in the polar group-containing olefin copolymer may be appropriately selected depending on the average molecular weight and desired physical properties. The content of the structural unit (B) in the polar group-containing olefin copolymer may have a lower limit of 0.01 mol% or more, preferably 0.02 mol% or more, 0.10 mol% or more, or 0.20 mol% or more, relative to 100 mol% of all structural units. On the other hand, the upper limit may be 20.00 mol% or less, preferably 10.00 mol% or less, 5.00 mol% or less, 3.00 mol% or less, or 1.00 mol% or less. Any combination of the upper and lower limits may be used. Among these, the content of the structural unit (B) in the polar group-containing olefin copolymer may particularly preferably be 0.02 mol % to 10.00 mol %, 0.10 mol % to 10.00 mol %, or 0.20 mol % to 10.00 mol %, relative to 100 mol % of all structural units.

[0059] The polar group-containing olefin copolymer of the present disclosure may further contain at least one other structural unit (C). When the polar group-containing olefin copolymer of the present disclosure contains other structural units (C), the content of the other structural units (C) in the polar group-containing olefin copolymer may be an upper limit of 10 mol% or less, preferably 6 mol% or less, more preferably 2 mol% or less, relative to 100 mol% of all structural units. The polar group-containing olefin copolymer of the present disclosure may have 0 mol% of other structural units (C), i.e., the total content of the structural units (A) and (B) in the polar group-containing olefin copolymer may be 100 mol% relative to 100 mol% of all structural units.

[0060] The structure derived from one molecule of each monomer is defined as one structural unit in the polar group-containing olefin copolymer. The amount of structural units is the ratio of each structural unit expressed in mol % when the total structural units in the polar group-containing olefin copolymer is taken as 100 mol %.

[0061] The polar group-containing olefin copolymer of the present disclosure may be a random copolymer, block copolymer, graft copolymer, etc., of the structural unit (A), the structural unit (B), and other structural units that may be contained as needed. Among these, a random copolymer that may contain a large amount of the structural unit (B) may be used.

[0062] The amount of structural units can be controlled by the following method. 1) Selection of catalyst 2) The amount of monomer that derives each structural unit added during polymerization 3) Polymerization pressure 4) Polymerization temperature Specific means for increasing the amount of the structural unit (B) in the copolymer include increasing the amount of the monomer (B) added during polymerization, decreasing the amount of the monomer (A), and increasing the polymerization temperature. For example, it is necessary to adjust these factors to control the copolymer to the desired range.

[0063] The amount of structural units in the polar group-containing olefin copolymer of the present disclosure is 1 H-NMR spectrum and 13 The C-NMR spectrum can be measured by the method described in the Examples below.

[0064] In particular, when the structural unit (A) is derived from ethylene, the polar group-containing olefin copolymer of the present disclosure 13 The degree of methyl branching calculated by C-NMR may be 20.0 or less, 15.0 or less, 10.0 or less, 8.0 or less, or 6.0 or less per 1,000 carbon atoms. When the degree of methyl branching satisfies this range, the elastic modulus is high and the mechanical strength of the molded product is likely to be high. The degree of methyl branching can be controlled by selecting the catalyst used in the polymerization and the polymerization temperature. A specific means for reducing the degree of methyl branching of an olefin copolymer is to lower the polymerization temperature. For example, these factors can be adjusted to control the copolymer to the desired range.

[0065] The number of methyl branches is measured as follows: First, the sum of the integrated intensities of the peaks due to carbons from 2 ppm to 60 ppm and from 170 ppm to 180 ppm (I トータル ) is normalized to 1,000. Next, the sum of the integrated intensity of the signal due to the methyl carbon of the methyl branch at 20 ppm, the integrated intensity of the signal due to the methine carbon of the methyl branch at 33 ppm, and the integrated intensity of the signal due to the methylene carbon of the methyl branch at 37 ppm is divided by 4 to obtain the value (I B1 ) and the number of methyl branches per 1,000 carbon atoms is B1 and is calculated using the following formula: Number of methyl branches (per 1000 carbons) = I B1 ×1000 / I トータル The chemical shifts are set to 1.98 ppm for the peak of the methyl carbon of hexamethyldisiloxane, and the chemical shifts of the peaks due to other carbons are based on this.

[0066] The weight average molecular weight (Mw) of the polar group-containing olefin copolymer of the present disclosure is usually in the range of 1,000 to 2,000,000, preferably 10,000 to 1,500,000, more preferably 20,000 to 1,000,000, more preferably 31,000 to 800,000, and even more preferably 35,000 to 800,000. When Mw is 1,000 or more, physical properties such as mechanical strength and impact resistance tend to be sufficient, while when Mw is 2,000,000 or less, difficulties in molding processing tend to be suppressed.

[0067] The number average molecular weight (Mn) of the polar group-containing olefin copolymer of the present disclosure is usually in the range of 1,000 to 2,000,000, preferably 3,000 to 1,500,000, more preferably 4,000 to 1,000,000, more preferably 5,000 to 800,000, and even more preferably 5,000 to 600,000. When Mn is 1,000 or more, physical properties such as mechanical strength and impact resistance tend to be sufficient, while when Mn is 2 million or less, difficulties in molding processing tend to be suppressed.

[0068] The ratio (Mw / Mn) of weight average molecular weight (Mw) to number average molecular weight (Mn) of the polar group-containing olefin copolymer of the present disclosure may be in the range of 1.5 to 5.0, preferably 2.0 to 4.0, and more preferably 2.2 to 3.5. When Mw / Mn is 1.5 or more, various processability tends to be sufficient, and when it is 5.0 or less, mechanical properties tend to be good. In the present disclosure, (Mw / Mn) may also be expressed as a molecular weight distribution parameter.

[0069] The weight average molecular weight (Mw) and number average molecular weight (Mn) in this disclosure are determined by gel permeation chromatography (GPC). The GPC measurement in the present disclosure can be performed by the method described in the Examples below.

[0070] 2. Method for producing polar group-containing olefin copolymer The method for producing a polar group-containing olefin copolymer of the present disclosure is a method for producing a polar group-containing olefin copolymer of the present disclosure, characterized in that the polar group-containing olefin copolymer is produced in the presence of a transition metal catalyst of Groups 4 to 10 of the periodic table.

[0071] Further, the method for producing a polar group-containing olefin copolymer of the present disclosure includes the steps of: The polymer is characterized by polymerizing the following monomer (A) and the following monomer (B). Monomer (A): At least one selected from the group consisting of ethylene and olefins having 3 to 20 carbon atoms Monomer (B): At least one selected from the group consisting of lactone monomers represented by the following general formula (1) and lactone monomers represented by the following general formula (2):

[0072] [ka] [In general formula (1), R 1 , R 2 , R3 , R 4 , R 5 and R 6 are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R 7 , R 8 and R 9 are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1, or 2. When n=0, adjacent carbon atoms are directly bonded to each other, and R 3 and R 4 does not exist.]

[0073] [ka] [In general formula (2), R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R 17 , R 18 and R 19 are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1, or 2. When n=0, adjacent carbon atoms are directly bonded to each other, and R 13 and R 14 does not exist.]

[0074] (1) Catalyst The polar group-containing olefin copolymer of the present disclosure may be polymerized in the presence of a catalyst containing a transition metal catalyst of Groups 4 to 10 of the periodic table. In this case, it is easy to produce a copolymer containing the structural unit (A) and the structural unit (B). The catalyst containing a transition metal catalyst of Groups 4 to 10 of the periodic table is not particularly limited as long as it is capable of polymerizing at least one monomer selected from the group consisting of ethylene and olefins having 3 to 20 carbon atoms, which derives the structural unit (A), and a lactone monomer having an ethylenically unsaturated group, which derives the structural unit (B). The transition metal catalyst may be, for example, a transition metal compound of Groups 5 to 10 of the periodic table, and further includes a transition metal compound of Groups 5 to 10 of the periodic table having a chelating ligand.

[0075] Specific examples of preferred transition metals include titanium, zirconium, hafnium, vanadium, niobium, tantalum, chromium, molybdenum, tungsten, manganese, iron, platinum, ruthenium, cobalt, rhodium, nickel, and palladium. Among these, transition metals of Groups 8 to 10 are preferred, and transition metals of Group 10 are more preferred. Examples of transition metals of Group 10 include nickel, palladium, and platinum. Nickel (Ni) and palladium (Pd) are particularly preferred. These transition metals may be used alone or in combination.

[0076] Chelating ligands have at least two atoms selected from the group consisting of P, N, O, C, and S, and include bidentate or multidentate ligands, and are electronically neutral or anionic. Exemplary structures are provided in the review by Brookhart et al. (Chem. Rev., 2000, 100, 1169). Preferred examples of the bidentate anionic P,O ligand include phosphorus sulfonate, phosphorus carboxylate, phosphorus phenoxide, phosphorus alkoxide, and phosphorus enolate. Preferred examples of the bidentate anionic N,O ligand include salicylaldiminate and pyridine carboxylate. Preferred examples of the bidentate anionic C,O ligand include carbene phenoxide, carbene alkoxide, and carbene carboxylate. Other examples include diimine ligands, diphenoxide ligands, and diamide ligands.

[0077] In terms of the polymer production efficiency, the molecular weight of the polymer, and copolymerizability with the monomer (A) and the monomer (B), the transition metal-containing catalyst is preferably a catalyst containing a late transition metal selected from the group consisting of Group 8 to Group 10 transition metals. Of these, a catalyst containing a Group 10 transition metal is preferred. Furthermore, a catalyst containing a Group 10 transition metal is preferred, and the catalyst has a chelating ligand containing one or more phosphorus atoms or oxygen atoms as a coordination site for the Group 10 transition metal.

[0078] In terms of the production efficiency of the polymer, the molecular weight of the polymer, and copolymerizability with the monomer (A) and the monomer (B), the transition metal-containing catalyst may be at least one selected from the group consisting of compounds represented by the following general formula (101), the following general formula (201), and the following general formula (202): Furthermore, the transition metal catalyst may be a transition metal catalyst in which a chelating phosphine compound or a chelating carbene compound is coordinated to nickel or palladium metal.

[0079] [ka] In general formula (101), M represents a Group 10 transition metal. Q represents a divalent group shown in "[ ]" of A[-S(=O)2-O-]M, A[-C(=O)-O-]M, A[-O-]M, A[-P(=O)(R)-O-]M, or A[-S-]M. R represents a hydrocarbon group having 1 to 30 carbon atoms which may have a functional group (however, A and M on both sides are written to indicate the bonding direction of the group). A is a divalent hydrocarbon group having 1 to 30 carbon atoms which connects Q and the phosphorus atom and may have a functional group. L represents a zero-valent ligand which can be detached from the metal. R 25 represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a functional group. 26 and R 27 R represents a hydrocarbon group having 1 to 30 carbon atoms which may have a functional group. 25 and L may form a ring, and R 26 and R 27 may form a ring, and R 26or R 27 may be bonded to A to form a ring.

[0080] In the general formula (101), M represents a Group 10 transition metal, and among these, Ni or Pd is preferred. Q represents a divalent group represented by -S(=O)2-O-, -C(=O)-O-, -O-, -P(=O)(R)-O-, or -S-, and is a moiety that coordinates one electron to M. In each of the above formulas, the left side is bonded to A, and the right side is bonded to M. Among these, -S(=O)2-O- is particularly preferred as Q from the viewpoint of catalytic activity. R represents a hydrocarbon group having 1 to 30 carbon atoms which may have a functional group, and R 25 The hydrocarbon group may be the same as the hydrocarbon group having 1 to 30 carbon atoms which may have a functional group in the above.

[0081] A is a divalent hydrocarbon group having 1 to 30 carbon atoms that links Q to the phosphorus atom, and the hydrocarbon group may have a functional group. The divalent hydrocarbon group having 1 to 30 carbon atoms is preferably a divalent hydrocarbon group having 1 to 12 carbon atoms, more preferably an alkylene group or an arylene group, and particularly preferably an arylene group.

[0082] The functional group of the hydrocarbon group in A is, for example, a halogen atom, -OR α , -CO2R α , -CO2M', -CON(R β )2, -COR α , -SR α , -SO2R α , -SOR α , -OSO2R α , -PO(OR α ) 2-y (R β ) y , -CN, -NHR α , -N(R α )2, -Si(OR β ) 3-x (R β ) x , -OSi(OR β ) 3-x (Rβ ) x , -NO2, -SO3M', -PO3M'2, -P(O)(OR α ) 2M′, or an epoxy-containing group, etc. (wherein R β represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and R α represents a hydrocarbon group having 1 to 20 carbon atoms, M' represents an alkali metal, an alkaline earth metal, ammonium, a quaternary ammonium or a phosphonium, x represents an integer of 0 to 3, and y represents an integer of 0 to 2). Examples of the hydrocarbon group having 1 to 20 carbon atoms herein include the same hydrocarbon groups having 1 to 20 carbon atoms as those of the hydrocarbon groups having 1 to 30 carbon atoms in the general formula (I) and the general formula (II).

[0083] Examples of the divalent hydrocarbon group having 1 to 30 carbon atoms represented by A include the following formulae (a-1) to (a-7). 101 are each independently a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms, or a functional group. 101 In the formula (I), examples of the hydrocarbon group having 1 to 30 carbon atoms include the same hydrocarbon groups having 1 to 30 carbon atoms as those in the general formula (I) and the general formula (II). Of the hydrocarbon groups having 1 to 30 carbon atoms, hydrocarbon groups having 1 to 20 carbon atoms are preferred, and hydrocarbon groups having 1 to 10 carbon atoms are more preferred. The divalent hydrocarbon group having 1 to 30 carbon atoms for A may be, among others, the following formula (a-7) in terms of catalytic activity.

[0084] [ka]

[0085] L represents a zero-valent ligand that can be removed from the metal. L is preferably a compound having an electron-donating group and capable of stabilizing the metal complex by coordinating with the transition metal M. L may be a hydrocarbon compound having 1 to 20 carbon atoms and having an oxygen atom, nitrogen atom, or sulfur atom as an atom capable of coordinating with the transition metal, or a hydrocarbon compound (which may contain a heteroatom) having a carbon-carbon unsaturated bond capable of coordinating with the transition metal. L preferably has 1 to 16 carbon atoms, more preferably 1 to 10 carbon atoms.

[0086] Preferred examples of L include pyridines, piperidines, alkyl ethers, aryl ethers, alkylaryl ethers, cyclic ethers, alkylnitrile derivatives, arylnitrile derivatives, alcohols, amides, aliphatic esters, aromatic esters, amines, and cyclic unsaturated hydrocarbons.

[0087] An example of L having a sulfur atom is dimethyl sulfoxide (DMSO). Examples of L having a nitrogen atom include trialkylamines having an alkyl group with 1 to 10 carbon atoms, dialkylamines having an alkyl group with 1 to 10 carbon atoms, pyridine, 2,6-dimethylpyridine (also known as 2,6-lutidine), aniline, 2,6-dimethylaniline, 2,6-diisopropylaniline, N,N,N',N'-tetramethylethylenediamine (TMEDA), 4-(N,N-dimethylamino)pyridine (DMAP), acetonitrile, benzonitrile, quinoline, 2-methylquinoline, etc. Examples of L having an oxygen atom include diethyl ether, tetrahydrofuran, and 1,2-dimethoxyethane. From the viewpoints of the stability and catalytic activity of the complex, L is preferably dimethyl sulfoxide (DMSO), pyridine, 2,6-dimethylpyridine (also known as 2,6-lutidine), or N,N,N',N'-tetramethylethylenediamine (TMEDA), and more preferably dimethyl sulfoxide (DMSO) or 2,6-dimethylpyridine (also known as 2,6-lutidine). In addition, R 25and L may form a ring. An example of such a ring is a cyclooct-1-enyl group, which is also a preferred embodiment in the present disclosure.

[0088] R 25 represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a functional group, and R 26 and R 27 represents a hydrocarbon group having 1 to 30 carbon atoms which may have a functional group. R 25 and R 26 and R 27 Examples of the hydrocarbon group having 1 to 30 carbon atoms in the general formula (I) and the general formula (II) include the same hydrocarbon groups having 1 to 30 carbon atoms. R 25 and R 26 and R 27 The functional group in may be the same as the functional group in A.

[0089] R 25 is preferably a hydrocarbon group having 1 to 20 carbon atoms, a halogen-substituted hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms substituted with an alkoxy group or an aryloxy group. The number of carbon atoms in the hydrocarbon group is more preferably 1 to 10. 25 Specifically, more preferably, the alkyl group has 1 to 3 carbon atoms, a benzyl group, a trifluoromethyl group, a pentafluorophenyl group, a 1-(methoxymethyl)ethyl group, a 1-(ethoxymethyl)ethyl group, a 1-(phenoxymethyl)ethyl group, or a 1-(2,6-dimethylphenoxymethyl)ethyl group, and even more preferably, a methyl group or a benzyl group.

[0090] R 26 and R 27 is in the vicinity of the transition metal M and exerts steric and / or electronic interactions with the transition metal M. To exert such an effect, R 26 and R 27 The bulkier the R 26 and R 27The preferred carbon number is 3 to 30, and even more preferably 6 to 20.

[0091] R 26 and R 27 are preferably an alkyl group having 3 to 10 carbon atoms which may have a functional group, a cycloalkyl group having 6 to 20 carbon atoms which may have a functional group, or an aryl group having 6 to 20 carbon atoms which may have a functional group. R 26 and R 27 In the formula (I), the alkyl group having 3 to 10 carbon atoms is preferably an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group.

[0092] R 26 and R 27 Examples of the cycloalkyl group having 6 to 20 carbon atoms which may have a functional group include a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like which may have a functional group and be substituted with a linear or branched alkyl group having 3 to 10 carbon atoms. Furthermore, it may be, for example, a cycloalkyl group described in paragraphs 0104 to 0113 of JP 2018-141138 A (X in paragraphs 0104 to 0113 of JP 2018-141138 A indicates the bonding position of P (phosphorus atom) in general formula (101) of the present disclosure).

[0093] R 26 and R 27 Among these, from the viewpoint of controlling the molecular weight of the polymer and the copolymerizability with polar monomers, R is preferably a cyclohexyl group which may be substituted with a linear or branched alkyl group having 3 to 10 carbon atoms, and more preferably a cyclohexyl group substituted with a linear or branched alkyl group having 3 to 10 carbon atoms. 26 and R 27 may be a cyclohexyl group or a 2-isopropyl-5-methylcyclohexyl group (menthyl group).

[0094] Also, R 26 and R 27In the formula, examples of the aryl group having 6 to 20 carbon atoms which may have a functional group include a phenyl group, a naphthyl group, and an anthracenyl group. The aryl group may have a functional group, and may further be substituted with a linear or branched alkyl group having 3 to 10 carbon atoms. The aryl group having 6 to 20 carbon atoms is preferably substituted with a functional group containing at least one of an oxygen atom and a nitrogen atom. When the aryl group having 6 to 20 carbon atoms is substituted with a functional group containing at least one of an oxygen atom and a nitrogen atom, the functional group is preferably substituted at the ortho position relative to the carbon bonded to phosphorus. By doing so, R 26 and R 27 This is because at least one of the oxygen atom and the nitrogen atom in the nucleus can be spatially arranged so as to have an interaction with the transition metal M.

[0095] Preferred R 26 and R 27Specific examples of the phenyl group include a 2-methoxyphenyl group, a 2,6-dimethoxyphenyl group, a 2,4,6-trimethoxyphenyl group, a 4-methyl-2,6-dimethoxyphenyl group, a 4-t-butyl-2,6-dimethoxyphenyl group, a 1,3-dimethoxy-2-naphthyl group, a 2,6-diethoxyphenyl group, a 2,4,6-triethoxyphenyl group, a 4-methyl-2,6-diethoxyphenyl group, a 4-t-butyl-2,6-diethoxyphenyl group, a 1,3-diethoxy- 2-naphthyl group, 2,6-diphenoxyphenyl group, 2,4,6-triphenoxyphenyl group, 4-methyl-2,6-diphenoxyphenyl group, 4-t-butyl-2,6-diphenoxyphenyl group, 1,3-diphenoxy-2-naphthyl group, 2,6-dimethoxymethylphenyl group, 2,4,6-trimethoxymethylphenyl group, 4-methyl-2,6-dimethoxymethylphenyl group, 4-t-butyl-2,6-dimethoxymethylphenyl group, 1,3-dimethoxymethylphenyl group t-butyl-2,6-diphenoxymethylphenyl group, 1,3-diphenoxymethyl-2-naphthyl group, 2,6-diphenoxymethylphenyl group, 2,4,6-triphenoxymethylphenyl group, 4-methyl-2,6-diphenoxymethylphenyl group, 4-t-butyl-2,6-diphenoxymethylphenyl group, 1,3-diphenoxymethyl-2-naphthyl group, 2,6-di(2-methoxyethyl)phenyl group, 2,4,6-tri(2-methoxyethyl)phenyl group, 4-methyl-2,6-di(2-methoxyethyl)phenyl group group, a 4-t-butyl-2,6-di(2-methoxyethyl)phenyl group, a 1,3-di(2-methoxyethyl)-2-naphthyl group, a 2,6-di(2-phenoxyethyl)phenyl group, a 2,4,6-tri(2-phenoxyethyl)phenyl group, a 4-methyl-2,6-di(2-phenoxyethyl)phenyl group, a 4-t-butyl-2,6-di(2-phenoxyethyl)phenyl group, and a 1,3-di(2-phenoxyethyl)-2-naphthyl group.

[0096] R 26 and R 27 may bond with A to form a ring structure. Specific examples include structures described in paragraphs 0120 to 0121 of JP-A No. 2018-141138 (examples here include the structures described in paragraphs 0120 to 0121 of JP-A No. 2018-141138). 26and A are bonded to form a ring structure, P and Q are the same as those in the general formula (101) of the present disclosure, and R 17 is R in the general formula (101) of the present disclosure 27 is synonymous with R 104 is R in the general formula (101) of the present disclosure 101 is synonymous with.

[0097] Among the compounds represented by general formula (101) of the present disclosure, a compound represented by the following general formula (102) is preferred from the viewpoint of polymer production efficiency.

[0098] [ka] (In general formula (102), M, L, R 25 , R 26 and R 27 are the same as those in the general formula (101), and R 111 , R 112 , R 113 and R 114 are each independently a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms, or a functional group.

[0099] In general formula (102), R 111 , R 112 , R 113 and R 114 The hydrocarbon group having 1 to 30 carbon atoms and the functional group in may be the same as those explained in A above. R 111 , R 112 , R 113 and R 114 may all be hydrogen atoms. R 111 The bulkier the polymer, the higher the molecular weight of the polymer. 111 may be appropriately selected from the substituents such as t-butyl group, trimethylsilyl group, phenyl group, 9-anthracenyl group, 4-t-butylphenyl group, 2,4-di-t-butylphenyl group, pentafluorophenyl group, and the like.

[0100] [ka]

[0101] In the general formula (201) or the general formula (202), M 201 represents a transition metal in Groups 8 to 10 of the periodic table. 201 Examples of the metals include Fe, Co, Ni, Pd, and Pt. L 201 and L 202 is M 201 L represents a ligand bound to each of the groups, each of which independently represents a hydrocarbon group having 1 to 20 carbon atoms and containing a halogen atom, a hydrogen atom, or a hetero atom. 201 and L 202 may be linked to each other to form a ring. 201 and L 202 Examples of the alkyl group include a halogen atom, a methyl group, a phenyl group, a benzyl group, pyridine, and 2,6-lutidine.

[0102] Z 201 is an oxygen atom, a sulfur atom, OR 203 , S.R. 203 , SO3, SO3R 203 , N=CR 203 R 204 , C.R. 203 =NR 204 , N(R 203 ), N(R 203 )2, P(R 203 ), P(R 203 )2, CO2, CO2R 203 , C(O)N(R 203 )2, CO, C(O)R 203 , SO2R 203 , SOR 203 , OSO2R 203 , P(O)(OR 203 ) 2-y (R 204 ) y , or P(R 203 )2(O) (where R 203 and R 204 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and y represents an integer of 0 to 2).

[0103] R 201 and R 202 are each independently a hydrogen atom or a hydrocarbon group having 1 to 40 carbon atoms which may contain a heteroatom. Specific examples of the hydrocarbon group having 1 to 40 carbon atoms which may contain a heteroatom include C(O)CH3, C(O)CH2CH3, CHOCH3, CHOCH2CH3, CH2NH2, CH2CH2NH2, etc. The hydrocarbon group is preferably a hydrocarbon group having 1 to 33 carbon atoms, and examples include an alkyl group, a cycloalkyl group, an aryl group, and combinations thereof. Preferred examples include a 1-propyl group, a 1-butyl group, a 1-pentyl group, a 1-hexyl group, a 1-heptyl group, a 1-octyl group, a 1-nonyl group, a 1-decyl group, a t-butyl group, a tricyclohexylmethyl group, a 1,1-dimethyl-2-phenylethyl group, an isopropyl group, a 1-dimethylpropyl group, a 2,4,6-trimethylphenyl group, a 2,6-diisopropylphenyl group, and a 2,6-dibenzhydryl-4-methylphenyl group. X 201 represents a saturated or unsaturated divalent hydrocarbon group having 3 to 9 carbon atoms, and X 201 may have a substituent on the ring formed by

[0104] R a is a hydrocarbon group having 1 to 10 carbon atoms which may contain a hydrogen atom or a heteroatom, and examples thereof include CH3, CH2CH3, C(O)CH3, C(O)CH2CH3, CH2OCH3, CH2OCH2CH3, CH2NH2, and CH2CH2NH2. R a is X 201 may be fused to a part of a ring consisting of:

[0105] A + represents the counter cation. + As an arbitrary cation, K + , Na + Examples include: M 201 Valence and Z 201 , L 201 and L 202Depending on the type of cation, the complex as a whole may be negatively charged. In this case, the counter cation A + Here, M 201 The valence of refers to the formal oxidation number used in organometallic chemistry. Specific examples of the compound represented by the general formula (201) or the general formula (202) can be found in, for example, JP-A 2016-135777 and J. Am. Chem. Soc. 2015, 137, 10934.

[0106] The transition metal complexes used in the present disclosure can be prepared by conventionally known methods. The compound represented by the general formula (101) can be produced, for example, by referring to JP-A-2018-141138. The compound represented by the general formula (201) or (202) can be produced, for example, by referring to JP-A-2016-135777. The transition metal-containing catalyst used in the present disclosure contains the above-mentioned transition metal complex as a main catalytic component, and may optionally contain an activator, a carrier, etc. Examples of the activator include alkylalumoxanes and boron-containing compounds, which are co-catalysts used in metallocene catalysts.

[0107] Any carrier can be used as long as it does not impair the gist of the present invention. Generally, inorganic oxides and polymer carriers are preferably used as the carrier. Specific examples of carriers include SiO2, Al2O3, MgO, ZrO2, TiO2, BO3, CaO, ZnO, BaO, ThO2, and mixtures thereof. Mixed oxides such as SiO2-Al2O3, SiO2-VO5, SiO2-TiO2, SiO2-MgO, and SiO2-Cr2O3 can also be used. Also usable are inorganic silicates, polyethylene carriers, polypropylene carriers, polystyrene carriers, polyacrylic acid carriers, polymethacrylic acid carriers, polyacrylic acid ester carriers, polyester carriers, polyamide carriers, and polyimide carriers. There are no particular limitations on the particle size, particle size distribution, pore volume, specific surface area, etc., of these carriers, and any carrier can be used.

[0108] (2) Monomer In the production method of the present disclosure, at least the following monomer (A) from which the structural unit (A) is derived and the following monomer (B) from which the structural unit (B) is derived may be polymerized. Monomer (A): At least one selected from the group consisting of ethylene and olefins having 3 to 20 carbon atoms Monomer (B): at least one selected from the group consisting of lactone monomers represented by the general formula (1) and lactone monomers represented by the general formula (2).

[0109] As the at least one monomer (A) selected from the group consisting of ethylene and olefins having 3 to 20 carbon atoms, the same monomer (A) as described above for the structural unit (A) can be used.

[0110] In the at least one monomer (B) selected from the group consisting of the lactone monomer represented by the general formula (1) and the lactone monomer represented by the general formula (2), 1 ~R 9 and n are each R 1 ~R 9 and n may be the same as those in the general formula (2), 11 ~R 19 and n are each R11 ~R 19 , and n may be the same.

[0111] Examples of the monomer (B) include, but are not limited to, the following structural units:

[0112] [ka]

[0113] The monomer (B) can be synthesized by a method known in the art, or a commercially available product can be used. The lactone monomer represented by the general formula (1) can be synthesized using, for example, carbon dioxide and a diene such as butadiene. Examples of dienes include 1,3-butadiene, 1,3-pentadiene, isoprene, and 1,2-butadiene. The lactone monomer represented by the general formula (1) can be synthesized with reference to, for example, J. Organomet. Chem. 1983, 255, 263-268 and British Patent Application Publication No. 2550876. The substituent in the lactone monomer represented by the general formula (1) may be introduced into 1,3-dienes by a known method.

[0114] Furthermore, the lactone monomer represented by the general formula (2) can be synthesized by referring to the intramolecular cyclization reaction of unsaturated carboxylic acids, for example, in SYNLETT, 2015, 26, 2237-2242, Chem. Sci. 2012, 3, 789-793, J. Org. Chem. 1993, 58, 5298-5300, etc. The substituent in the lactone monomer represented by the general formula (2) may be introduced by a known method in the synthesis of unsaturated carboxylic acids, or may be introduced by a known method in the lactone monomer. Alternatively, the substituent in the structural unit (B) may be introduced after polymerization of the lactone monomer.

[0115] As the monomer (C) from which the other structural unit (C) is derived, a monomer copolymerizable with the monomer (A) in the presence of the transition metal catalyst of Groups 4 to 10 of the periodic table can be used, and the same monomers as those described for the structural unit (C) can be used.

[0116] (3) Polymerization method The polymerization method in the production method of the polar group-containing olefin copolymer of the present disclosure is not limited. Solution polymerization in which all the produced polymer is dissolved in the medium, slurry polymerization in which at least a part of the produced polymer becomes a slurry in the medium, or bulk polymerization in which the liquefied monomer itself is used as the medium, etc., are used. The polymerization method may be any of batch polymerization, semi-batch polymerization, and continuous polymerization. For specific manufacturing processes and conditions, reference can be made to, for example, Japanese Patent Application Laid-Open Nos. 2010-260913 and 2010-202647.

[0117] The unreacted monomers and the medium may be separated from the produced polymer and recycled for reuse. When recycling, these monomers and the medium may be purified and reused, or they may be reused without purification. Conventional known methods can be used to separate the produced polymer from the unreacted monomers and the medium. For example, methods such as filtration, centrifugation, solvent extraction, and reprecipitation using a poor solvent can be used.

[0118] There are no particular limitations on the polymerization temperature, polymerization pressure and polymerization time, but they can usually be optimally set within the following ranges, taking into consideration productivity and process capacity. That is, the polymerization temperature is usually -20°C to 290°C, preferably 0°C to 250°C, more preferably 0°C to 200°C, even more preferably 10°C to 150°C, and particularly preferably 20°C to 100°C. The polymerization pressure is 0.1 MPa to 100 MPa, preferably 0.3 MPa to 90 MPa, more preferably 0.5 MPa to 80 MPa, even more preferably 1.0 MPa to 70 MPa, and particularly preferably 1.3 MPa to 60 MPa. The polymerization time can be selected from the range of 0.1 minute to 50 hours, preferably 0.5 minutes to 40 hours, and more preferably 1 minute to 30 hours. In the present disclosure, polymerization is generally carried out under an inert gas atmosphere, such as a nitrogen or argon atmosphere, with a nitrogen atmosphere being preferred.

[0119] There are no particular limitations on the supply of catalyst and monomer to the polymerization reactor, and various supply methods can be used depending on the purpose. For example, in the case of batch polymerization, a method can be used in which a predetermined amount of monomer is supplied to the polymerization reactor in advance and the catalyst is then supplied thereto. In this case, additional monomer or additional catalyst may be supplied to the polymerization reactor. Furthermore, in the case of continuous polymerization, a method can be used in which predetermined amounts of monomer and catalyst are supplied to the polymerization reactor continuously or intermittently and the polymerization reaction is carried out continuously.

[0120] The composition of the copolymer can be controlled, for example, by the following methods. 1) Changing the monomer feed ratio 2) Utilizing differences in monomer reactivity ratios due to differences in catalyst structure 3) Utilizing the polymerization temperature dependence of the monomer reactivity ratio

[0121] The molecular weight of the copolymer can be controlled by a conventionally known method, for example, the following method. 1) Control of polymerization temperature 2) Control of monomer concentration 3) Control of the ligand structure in transition metal complexes 4) Use of known chain transfer agents such as hydrogen [Example]

[0122] The present disclosure will now be described in detail with reference to examples, but the present disclosure is not limited to these examples as long as they do not deviate from the spirit of the present disclosure. The physical properties of the polar group-containing olefin copolymer and the like were measured by the following methods.

[0123] [Structure of polar group-containing olefin copolymer] The structure of the polar group-containing olefin copolymer was prepared using Ascend 500 manufactured by BRUKER Co., Ltd. or AVANCE 400 manufactured by BRUKER Co., Ltd. 1 H-NMR and 13 This was determined by C-NMR analysis. The solvent used for NMR measurements was 1,1,2,2-tetrachloroethane-d2. 1 The polymer concentration for H-NMR measurement was 5% by mass. 13 The polymer concentration for C-NMR was 15% by mass. NMR measurements were performed at 120°C. Alternatively, some of the NMR measurements were performed at 120°C by heating and dissolving approximately 150 mg of polar group-containing olefin copolymer in 2.4 mL of a mixed solvent of 1,2-dichlorobenzene:bromobenzene-d5 = 1:2 to prepare a homogeneous solution. 1 H-NMR measurement was carried out under the following conditions, and quantitative analysis was carried out. Pulse: 50 microsecond 30° pulse Spectral width: 10kHz Relaxation time: 5 seconds Capture time: 3.2 seconds FID accumulation count: 128 times 13 C-NMR measurements were performed using chromium(III) acetylacetonate as a relaxation reagent using the inverse gated decoupling method under the following conditions, and quantitative analysis was performed. Pulse: 9.0 microsecond 90° pulse or 15.8 microsecond 90° pulse Spectral width: 31kHz or 25kHz Relaxation time: 10 seconds or 50 seconds Capture time: 10 seconds or 1.5 seconds FID accumulation count: 5,000 to 10,000 or 1,024

[0124] [Content of structural unit (B) in polar group-containing olefin copolymer] The content of the structural unit (B) is 1 H-NMR was used as follows. As an example of the ethylene copolymer, copolymer 8 of Example 8 1 H-NMR is shown in Figure 1. The unique isolated peak at chemical shift 4.2-4.3 ppm (position of C) in Figure 1 corresponds to 1H (one hydrogen) from the structural unit (B), and its peak area was designated as IB. The sum of all peak areas excluding the solvent was designated as IA. The ratio of the structural unit (B) to all monomer units was calculated as IB × 4 / (IA-IB × 8). As an example of the propylene copolymer, copolymer 11 of Example 11 1 H-NMR is shown in Figure 2. The specific isolated peak at chemical shift 4.2-4.3 ppm (position of C) in Figure 2 corresponds to 1H from structural unit (B), and its peak area was designated as IB. The sum of all peak areas excluding the solvent was designated as IA. The ratio of structural unit (B) to all monomer units was calculated as IB × 6 / (IA-IB × 6).

[0125] [Content of other structural units in polar group-containing olefin copolymer] The content of each structural unit when a structural unit derived from methyl acrylate is included as another structural unit (C) is shown with reverse gate decoupling. 13 C-NMR was used as follows. As an example of the ethylene copolymer, copolymer 12 of Example 12 13 C-NMR is shown in Figure 3. In Figure 3, the unique isolated peak at chemical shifts of 13-14 ppm (position D) corresponds to 1C (one carbon) derived from structural unit (B). The unique isolated peak at chemical shifts of 22-23 ppm (position F) corresponds to 1C derived from structural unit (B). The unique isolated peak at chemical shifts of 24-25 ppm (position G) corresponds to 1C derived from structural unit (B). The unique isolated peak at chemical shifts of 126-128 ppm (position B) corresponds to 1C derived from structural unit (B). The unique isolated peak at chemical shifts of 138-140 ppm (position C) corresponds to 1C derived from structural unit (B). The average area of ​​these five peaks was designated IB. The unique isolated peak at chemical shifts of 176-177 ppm (position b) in Figure 3 corresponds to 1C derived from another structural unit (methyl acrylate), and its peak area was designated IC. The sum of all peak areas excluding the solvent was designated IA. The ratio of the structural unit (B) to all monomer units was calculated as (100 × IB) / (((IA-IB × 9-IC × 4) / 2) + IB + IC). The ratio of the structural unit (methyl acrylate) to all monomer units was calculated as (100 × IC) / (((IA-IB × 9-IC × 4) / 2) + IB + IC).

[0126] [Number average molecular weight and weight average molecular weight] The number average molecular weight (Mn) and weight average molecular weight (Mw) were calculated under the following conditions by size exclusion chromatography using polystyrene as a molecular weight standard. Apparatus: Tosoh Corporation high-temperature GPC apparatus HLC-8321GPC / HT Column: Tosoh Corporation, TSKgel GMHHR-H(S)HT column (7.8 mm I.D. x 30 cm, two columns in series) Solvent: 1,2-dichlorobenzene Temperature: 145℃ or Equipment: High temperature GPC equipment manufactured by Waters Co., Ltd., ALC / GPC 150C Column: Showa Denko AT-806MS column (8.0 mm I.D. x 25 cm, three columns in series) Solvent: 1,2-dichlorobenzene Temperature: 140℃

[0127] [Synthesis of transition metal complexes] (Synthesis Example 1) Transition metal complex (A) represented by the following chemical formula (A), in which R is menthyl (2-isopropyl-5-methylcyclohexyl) and Lut is 2,6-dimethylpyridine, was synthesized as described in JP 2017-031300 A. In this specification, Me represents methyl.

[0128] [ka]

[0129] (Synthesis Example 2) A transition metal complex (B) represented by the chemical formula (A) in which all R's are cyclohexyl and Lut is 2,6-dimethylpyridine was synthesized as described in JP-A-2011-068881.

[0130] (Synthesis Example 3) A transition metal complex (C) represented by the chemical formula (A) in which all R's are isopropyl and Lut is 2,6-dimethylpyridine was synthesized as described in JP-A-2013-079347.

[0131] (Synthesis Example 4) A transition metal complex (D) represented by the chemical formula (A) in which all R's are 2-methoxyphenyl and Lut is 2,6-dimethylpyridine was synthesized as described in JP-A-2007-046032.

[0132] (Synthesis Example 5) A transition metal complex (E) represented by the following chemical formula (B), in which R is 2,4,6-trimethylphenyl and Lut is 2,6-dimethylpyridine, was synthesized as described in J. Am. Chem. Soc. 2015, 137, 10934.

[0133] [ka]

[0134] (Synthesis Example 6) A transition metal complex (F) represented by the chemical formula (B) in which R is 2,6-diisopropylphenyl and Lut is 2,6-dimethylpyridine was synthesized as described in J. Am. Chem. Soc. 2015, 137, 10934.

[0135] Example 1 In a nitrogen atmosphere, a transition metal complex (A) (6.9 mg, 0.010 mmol) as a catalyst, toluene (10 mL) as a solvent, and 6-ethenyl-3-ethylidenetetrahydro-2H-pyran-2-one (1.0 mL, 6.6 mmol) as a monomer (B) were sequentially added to a 50 mL autoclave. The autoclave was pressurized with ethylene (monomer (A)) (3.0 MPa) and stirred at a reaction temperature of 80°C for 3 hours. The autoclave was returned to room temperature, and methanol (20 mL) was added. The precipitated solid was collected by filtration, washed with methanol, and dried under reduced pressure. The resulting polar group-containing olefin copolymer 1 weighed 509 mg. The analytical results of the polar group-containing olefin copolymer 1 are shown in Table 1.

[0136] Example 2 The same procedure as in Example 1 was carried out, except that the catalyst was changed to transition metal complex (B) (5.8 mg, 0.010 mmol). The amount of the obtained polar group-containing olefin copolymer 2 was 1,479 mg. The results of various analyses of the polar group-containing olefin copolymer 2 are shown in Table 1.

[0137] Example 3 The same procedure as in Example 1 was carried out, except that the catalyst was changed to a transition metal complex (C) (5.0 mg, 0.010 mmol). The amount of the obtained polar group-containing olefin copolymer 3 was 549 mg. The results of various analyses of the polar group-containing olefin copolymer 3 are shown in Table 1.

[0138] Example 4 The same procedure as in Example 1 was carried out, except that the catalyst was changed to transition metal complex (D) (6.3 mg, 0.010 mmol). The amount of the obtained polar group-containing olefin copolymer 4 was 382 mg. The results of various analyses of the polar group-containing olefin copolymer 4 are shown in Table 1.

[0139] Example 5 Except for changing the catalyst to transition metal complex (E) (5.7 mg, 0.010 mmol), the same procedure as in Example 1 was carried out. The amount of polar group-containing olefin copolymer 5 obtained was 17 mg. The results of various analyses of the polar group-containing olefin copolymer 5 are shown in Table 1.

[0140] Example 6 The same procedure as in Example 1 was carried out, except that the catalyst was changed to a transition metal complex (F) (5.3 mg, 0.010 mmol). The amount of the obtained polar group-containing olefin copolymer 6 was 73 mg. The results of various analyses of the polar group-containing olefin copolymer 6 are shown in Table 1.

[0141] Example 7 The same procedure as in Example 6 was carried out, except that the reaction temperature was changed to 60° C. The amount of the obtained polar group-containing olefin copolymer 7 was 61 mg. The results of various analyses of the polar group-containing olefin copolymer 7 are shown in Table 1.

[0142] Example 8 The same procedure as in Example 6 was carried out, except that the reaction temperature was changed to 100° C. The amount of the obtained polar group-containing olefin copolymer 8 was 61 mg. The results of various analyses of the polar group-containing olefin copolymer 8 are shown in Table 1.

[0143] Example 9 The same procedure as in Example 6 was repeated, except that the amount of 6-ethenyl-3-ethylidenetetrahydro-2H-pyran-2-one used as monomer (B) was changed to 0.5 mL, 3.3 mmol. The amount of the polar group-containing olefin copolymer 9 obtained was 150 mg. The results of various analyses of the polar group-containing olefin copolymer 9 are shown in Table 1.

[0144] Example 10 The same procedure as in Example 6 was repeated, except that the amount of 6-ethenyl-3-ethylidenetetrahydro-2H-pyran-2-one used as monomer (B) was changed to 0.2 mL, 1.3 mmol. The amount of the polar group-containing olefin copolymer 10 obtained was 284 mg. The results of various analyses of the polar group-containing olefin copolymer 10 are shown in Table 1.

[0145] Example 11 In a nitrogen atmosphere, a transition metal complex (E) (5.7 mg, 0.010 mmol) as a catalyst, toluene (10 mL) as a solvent, and 6-ethenyl-3-ethylidenetetrahydro-2H-pyran-2-one (0.1 mL, 0.66 mmol) as a monomer (B) were sequentially added to a 50 mL autoclave. The autoclave was cooled to 0°C, pressurized with propylene (monomer (A)) (10 g), sealed, and stirred at a reaction temperature of 80°C for 12 hours. The autoclave was returned to room temperature, and methanol (20 mL) was added. The precipitated solid was collected by filtration, washed with methanol, and dried under reduced pressure. The resulting polar group-containing olefin copolymer 11 weighed 50 mg. The polar group-containing olefin copolymer 11 had a number average molecular weight of 2700, a molecular weight distribution Mw / Mn of 2.1, and a structural unit (B) content of 1.9 mol%.

[0146] Example 12 In a nitrogen atmosphere, a transition metal complex (C) (5.0 mg, 0.010 mmol) as a catalyst, toluene (10 mL) as a solvent, 6-ethenyl-3-ethylidenetetrahydro-2H-pyran-2-one (1.0 mL, 6.6 mmol) as a monomer (B), and methyl acrylate (1.0 mL, 11 mmol) as a monomer (C) that will become another structural unit were sequentially added to a 50 mL autoclave. The autoclave was pressurized with ethylene (monomer (A)) (3.0 MPa) and stirred at a reaction temperature of 80°C for 3 hours. The autoclave was returned to room temperature, and methanol (20 mL) was added. The precipitated solid was collected by filtration, washed with methanol, and dried under reduced pressure. The resulting polar group-containing olefin copolymer 12 weighed 876 mg. The polar group-containing olefin copolymer 12 had a number average molecular weight of 126,600, a molecular weight distribution Mw / Mn of 1.0, a content of structural units (B) of 0.14 mol%, and a content of structural units derived from methyl acrylate (other structural units (C)) of 0.78 mol%, and a methyl branching degree of 0.22 per 1,000 carbon atoms.

[0147] [Table 1]

[0148] The polar group-containing olefin copolymers of Examples 1 to 12 did not contain any structural units derived from lactone monomers other than the structural unit (B). [Industrial Applicability]

[0149] The novel polar group-containing olefin copolymer of the present disclosure is a novel polar group-containing olefin copolymer in which a lactone structure is introduced into a side chain of the polymer chain, and can be applied in various ways to enhance the functionality of olefin-based polymers. The polar group-containing olefin copolymer of the present disclosure can be easily produced into a polar group-containing olefin copolymer having an acid or alcohol by, for example, hydrolyzing the lactone structure of the introduced side chain, and the carboxy group or hydroxyl group can be utilized. Furthermore, when the polar group-containing olefin copolymer of the present disclosure has a structural unit represented by the general formula (I), for example, it has an ethylenically unsaturated group in the side chain, and therefore can be post-modified, and for example, can be crosslinked, and is also promising as a macromonomer. When the polar group-containing olefin copolymer of the present disclosure has a structural unit represented by the general formula (I), for example, it has an enone structure in the side chain, and therefore can be used as a substrate for, for example, a Michael addition reaction. As described above, the polar group-containing olefin copolymer of the present disclosure is expected to be a raw material that can be converted into a variety of composite materials. Furthermore, since the 6-membered lactone monomer having an ethylenically unsaturated group that derives the structural unit (B) can also be derived from carbon dioxide, the polar group-containing olefin copolymer of the present disclosure has added value as a carbon recycled resin.

Claims

1. a structural unit (A) derived from at least one monomer selected from the group consisting of ethylene and an olefin having 3 to 20 carbon atoms; At least one structural unit (B) selected from the group consisting of structural units represented by the following general formula (I) and structural units represented by the following general formula (II), A polar group-containing olefin copolymer comprising: 【Chemistry 1】 [In general formula (I), R １ , R ２ , R ３ , R ４ , R ５ and R ６ are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R ７ , R ８ and R ９ are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1 or 2, and when n=0, adjacent carbon atoms are directly bonded to each other, and R ３ and R ４ does not exist.] 【Chemistry 2】 [In general formula (II), R １１ , R １２ , R １３ , R １４ , R １５ and R １６ are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R １７ , R １８ and R １９ are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1 or 2, and when n=0, adjacent carbon atoms are directly bonded to each other, and R １３ and R １４ does not exist.]

2. 2. The polar group-containing olefin copolymer according to claim 1, characterized in that the ratio (Mw / Mn) of weight average molecular weight (Mw) to number average molecular weight (Mn) determined by gel permeation chromatography (GPC) is in the range of 1.5 to 5.

0.

3. The structural unit (A) is derived from ethylene, and １３ 3. The polar group-containing olefin copolymer according to claim 1, wherein the degree of methyl branching calculated by C-NMR is 20.0 or less per 1,000 carbon atoms.

4. 3. A method for producing the polar group-containing olefin copolymer according to claim 1, wherein the polar group-containing olefin copolymer is produced in the presence of a transition metal catalyst of Groups 4 to 10 of the periodic table.

5. 5. The method for producing a polar group-containing olefin copolymer according to claim 4, wherein the transition metal catalyst is a transition metal catalyst in which a chelating phosphine compound or a chelating carbene compound is coordinated to nickel or palladium metal.

6. In the presence of a catalyst containing a transition metal of Groups 4 to 10 of the periodic table, A method for producing a polar group-containing olefin copolymer, comprising polymerizing the following monomer (A) and the following monomer (B): Monomer (A): At least one selected from the group consisting of ethylene and olefins having 3 to 20 carbon atoms Monomer (B): At least one selected from the group consisting of lactone monomers represented by the following general formula (1) and lactone monomers represented by the following general formula (2): 【Transformation 3】 [In general formula (1), R １ , R ２ , R ３ , R ４ , R ５ and R ６ are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R ７ , R ８ and R ９ are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1 or 2, and when n=0, adjacent carbon atoms are directly bonded to each other, and R ３ and R ４ does not exist.] 【Chemistry 4】 [In general formula (2), R １１ , R １２ , R １３ , R １４ , R １５ and R １６ are each independently a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R １７ , R １８ and R １９ are each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, n is 0, 1 or 2, and when n=0, adjacent carbon atoms are directly bonded to each other, and R １３ and R １４ does not exist.]

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