Modified polyolefin resin composition and use thereof

Abstract

Provided is a modified polyolefin resin composition which has sufficient fluidity in a specific temperature range, has sufficient adhesion to a polyolefin base material, has excellent adhesion to a plastic material, and has sufficient antistatic performance. Specifically, the present invention provides a modified polyolefin resin composition containing an acid-modified polyolefin resin (A), a polyetheramine (B), a compound (C) having a polymerizable unsaturated group, and an ionic liquid (D).

Description

TECHNICAL FIELD

[0001] The present application relates to a modified polyolefin resin composition and use of the resin composition. BACKGROUND

[0002] In the past, polyolefin-based resins such as polypropylene, polyethylene, ethylene-propylene copolymer, ethylene-propylene-diene copolymer, polybutylene, poly(4-methyl-1-pentene), and the like have been used in fields such as automobile parts, electrical parts, building materials, packaging films, and the like because they are relatively inexpensive and have excellent properties such as chemical resistance, water resistance, heat resistance, and the like.

[0003] On the other hand, since polyolefin-based resins are crystalline and nonpolar, it is difficult to apply coating, adhesion, and the like to polyolefin-based resins.

[0004] Therefore, chlorinated polyolefins having strong adhesion to polyolefin-based resins are widely used as adhesive resins (for example, Patent Document 1, Patent Document 2).

[0005] Furthermore, from the viewpoint of improving the adhesion (adhesion) of chlorinated polyolefin resins to polyolefin-based substrates and the viewpoint of simultaneously improving the adhesion (adhesion) to plastics other than polyolefin-based resins, there are adhesive compositions using a mixture of chlorinated polyolefin and acrylic resin, polyurethane resin, or polyester resin, and chlorinated polyolefin grafted with these resins (for example, Patent Document 3, Patent Document 4).

[0006] Further, an antistatic agent is usually mixed into polypropylene-based resins to be molded to suppress the generation of static electricity (for example, Patent Document 5, Patent Document 6, and the like). PRIOR ART DOCUMENTS PATENT DOCUMENTS

[0007] [Patent Document 1] Japanese Patent Application Laid-Open (JP-A) No. 59-75958 [Patent Document 2] Japanese Patent Application Laid-Open (JP-A) No. 60-99138 [Patent Document 3] Japanese Patent Application Laid-Open (JP-A) No. 6-16746 [Patent Document 4] Japanese Patent Application Laid-Open (JP-A) No. 8-12913 [Patent Document 5] Japanese Patent Application Laid-Open (JP-A) No. 2009-108259 [Patent Document 6] Japanese Patent Application Laid-Open (JP-A) No. 2020-33483 SUMMARY PROBLEMS TO BE SOLVED BY THE INVENTION

[0008] However, since the mixture and the adhesive composition described in Patent Literatures 3 and 4 are generally used in a state of being dissolved in an organic solvent such as toluene or xylene, a large amount of the organic solvent is released into the atmosphere at the time of coating, which is not preferable from the viewpoint of the environment, hygiene, and the like.

[0009] Further, the mixture and the adhesive composition described in Patent Literatures 3 and 4 have problems of poor flowability and poor adhesion to a polyolefin-based substrate.

[0010] Further, since a polyolefin-based substrate and plastic materials such as polyethylene terephthalate (PET) and ABS are not substantially excellent in conductivity, there is a problem that dust is attached to a molded article by static electricity, which deteriorates the appearance.

[0011] When a polypropylene film containing the antistatic agent described in Patent Literature 5 is layered with other films using an adhesive, there is a problem that the antistatic agent is adsorbed to the adhesive, and the antistatic performance cannot be exhibited.

[0012] When coating or printing is applied to a molded article using the antistatic agent described in Patent Literature 6, there is a problem such as a decrease in adhesion to a paint or a printing ink.

[0013] The present application was made in view of the above-described circumstances, and an object thereof is to provide a modified polyolefin resin composition having sufficient flowability in a specific temperature range, sufficient adhesion to a polyolefin-based substrate, excellent adhesion to plastic materials, and sufficient antistatic performance.

Means for solving the problem

[0014] The present inventors and the like made intensive studies on dispersing and / or dissolving an acid-modified polyolefin resin in a compound having a polymerizable unsaturated group, and as a result, found that a modified polyolefin resin composition containing an acid-modified polyolefin resin, a polyether amine, a compound having a polymerizable unsaturated group, and an ionic liquid can solve the above-described problems, and completed the present application.

[0015] The present application includes, for example, the subject matter described in the following items. Item 1. A modified polyolefin resin composition containing an acid-modified polyolefin resin (A), a polyether amine (B), a compound having a polymerizable unsaturated group (C), and an ionic liquid (D).

Effects of the Invention

[0016] The modified polyolefin resin composition of the present application has sufficient flowability in a specific temperature range, has sufficient adhesion to a polyolefin base material, has excellent adhesion to a plastic material, and has sufficient antistatic properties. Since the modified polyolefin resin composition of the present application exhibits sufficient flowability in a specific temperature range, it can be preferably used as a liquid modified polyolefin resin composition for various applications. DETAILED DESCRIPTION

[0017] The preferred embodiments of the present application are described in detail below. The description of the constituting conditions described below is sometimes based on representative embodiments and specific examples, and the present application is not limited to such embodiments.

[0018] In the present specification, the expressions "containing" and "including" include the concepts of "consisting essentially of" and "consisting of".

[0019] In the numerical ranges described in the present specification, the upper limit value or the lower limit value of the numerical range of a certain stage can be arbitrarily combined with the upper limit value or the lower limit value of the numerical range of another stage. In addition, in the numerical ranges described in the present specification, the upper limit value or the lower limit value of the numerical range can be replaced with the value shown in the examples or the value derived uniquely from the examples. Further, in the present specification, the numerical values connected with "~" represent the numerical range including the numerical values before and after "~" as the lower limit value and the upper limit value.

[0020] In the present specification, "A and / or B" means "one of A and B" or "both of A and B", specifically, means "A", "B", or "A and B".

[0021] In the present specification, "n-" means "normal", "i-" or "iso-" means "iso", and "tert-" or "t-" means "tert".

[0022] In the present specification, "(meth)acrylic acid" includes both of acrylic acid and methacrylic acid, and "(meth)acrylate" includes both of acrylate and methacrylate.

[0023] In the present specification, "acryloyl" is represented by "CH2=CHC(=O)-", "methacryloyl" is represented by "CH2=C(CH3)C(=O)-", acryloyloxy is represented by "CH2=CHC(=O)O-", and methacryloyloxy is represented by "CH2=C(CH3)C(=O)O-".

[0024] In the present specification, "cation" means a singly charged positive atom or a positively charged atomic group. In the present specification, "anion" means a singly charged negative atom or a negatively charged atomic group.

[0025] (Modified polyolefin resin composition) The modified polyolefin resin composition of the present application contains an acid-modified polyolefin resin (A), a polyether amine (B), a compound having a polymerizable unsaturated group (C), and an ionic liquid (D) as essential components.

[0026] As one embodiment, the modified polyolefin resin composition generally has sufficient flowability in a range of 25°C or higher and 80°C or lower. In the present specification, a resin composition having flowability, for example, means a uniform liquid composition not containing resin coarse particles, agglomerates, or the like.

[0027] As one embodiment, the modified polyolefin resin composition generally means a resin composition that flows when a glass bottle is tilted in a range of 25°C or higher and 80°C or lower. As one embodiment, a resin composition having flowability also generally includes a resin composition that is flowable by applying mechanical shearing in a range of 25°C or higher and 80°C or lower.

[0028] As one embodiment, the total content ratio of the acid-modified polyolefin resin (A), the polyether amine (B), the compound having a polymerizable unsaturated group (C), and the ionic liquid (D) is preferably in the order of more than 50% by mass, 55% by mass or more, 60% by mass or more, 65% by mass or more, 70% by mass or more, 75% by mass or more, 80% by mass or more, 85% by mass or more, 90% by mass or more, 92.5% by mass or more, 95% by mass or more, 97.5% by mass or more, 99% by mass or more, 99.5% by mass or more, 99.9% by mass or more, 99.95% by mass or more, and 99.99% by mass or more, with respect to the total mass of the modified polyolefin resin composition.

[0029] <Acid-modified polyolefin resin (A)> The present application contains an acid-modified polyolefin resin (A). The acid-modified polyolefin resin (A) is a polymer obtained by graft polymerization of a polyolefin resin with an α,β-unsaturated carboxylic acid or an acid anhydride thereof. In other words, the acid-modified polyolefin resin (A) is a graft polymer having a structure in which a polyolefin resin is grafted with an α,β-unsaturated carboxylic acid or an acid anhydride thereof.

[0030] The polyolefin resin generally has a structural unit derived from an α-olefin. As the α-olefin, for example, an α-olefin having 2 to 20 carbon atoms (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) such as ethylene, propylene, 1-butene, isobutylene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-heptene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene, and the like can be exemplified.

[0031] The polyolefin resin can be an olefin polymer containing only one structural unit derived from an α-olefin, or a copolymer of olefin polymers containing two or more structural units derived from α-olefins.

[0032] As one embodiment, the polyolefin resin is generally a petroleum-derived polyolefin resin. The petroleum-derived polyolefin resin refers to a polyolefin-based resin synthesized from an olefin derived from petroleum.

[0033] The petroleum-derived olefin, for example, petroleum naphtha, ethane, LPG (Liquefied Petroleum Gas), NGL (Natural Gas Liquid), gas oil, and the like, is an olefin produced by thermal cracking of a petroleum chemical raw material.

[0034] As one embodiment, as the petroleum-derived polyolefin resin, for example, homopolypropylene (propylene homopolymer), propylene-α-olefin copolymer, homopolyethylene (ethylene homopolymer), ethylene-α-olefin copolymer, poly-1-butene, and 1-butene-α-olefin copolymer, and the like can be exemplified. These polyolefin resins can be used individually or in combination of two or more. As one embodiment, among these polyolefin resins, homopolypropylene and / or propylene-α-olefin copolymer is preferable.

[0035] As one embodiment, the acid-modified polyolefin resin (A) is preferably a graft polymer having a structure in which homopolypropylene or propylene-α-olefin copolymer is grafted with α,β-unsaturated carboxylic acid or an acid anhydride thereof.

[0036] The propylene-α-olefin copolymer is a copolymer of propylene and an α-olefin. As the α-olefin, for example, ethylene; 1-butene, isobutene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-heptene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene, and the like α-olefin having 4 to 20 (4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) carbon atoms, and the like can be exemplified. These α-olefins can be used individually or in combination of two or more.

[0037] As one embodiment, the content of the propylene component in the propylene-α-olefin copolymer is preferably 50 mol% or more, more preferably 60 mol% or more, and still more preferably 70 mol% or more. As one embodiment, when the content of the propylene component in the propylene-α-olefin copolymer is 50 mol% or more, the adhesion of the modified polyolefin resin composition to the polyolefin-based substrate (particularly, polypropylene-based substrate) and the plastic material (particularly, PET and ABS) becomes further good.

[0038] The ethylene-α-olefin copolymer is a copolymer of ethylene and an α-olefin. As the α-olefin, for example, there can be mentioned propylene, 1-butene, isobutene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-heptene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene, and the like α-olefins having 3 to 20 (3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) carbon atoms. These α-olefins can be used individually or in combination of two or more.

[0039] As one embodiment, the content of the ethylene component in the ethylene-α-olefin copolymer is preferably 75 mol% or more. When the content of the ethylene component in the ethylene-α-olefin copolymer is 75 mol% or more, the adhesion of the modified polyolefin resin composition to the polyolefin substrate (particularly, polyethylene substrate) and the plastic material (particularly, PET and ABS) becomes further good.

[0040] The 1-butene-α-olefin copolymer refers to a copolymer of 1-butene and an α-olefin. As the α-olefin, for example, there can be mentioned ethylene; propylene; 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-heptene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene, and the like α-olefins having 5 to 20 (5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) carbon atoms. These α-olefins can be used individually or in combination of two or more.

[0041] As one embodiment, the content of the 1-butene component in the 1-butene-α-olefin copolymer is preferably 65 mol% or more. When the content of the 1-butene component in the 1-butene-α-olefin copolymer is 65 mol% or more, the adhesion of the modified polyolefin resin composition of the present embodiment to the polyolefin substrate (particularly, polypropylene substrate or poly-1-butene substrate) and the plastic material (particularly, PET and ABS) becomes further good.

[0042] As one embodiment, the total content of the α,β-unsaturated carboxylic acid and anhydride thereof in the acid-modified polyolefin resin (A) is preferably 0.5 to 10 mass%, more preferably 0.7 to 6 mass%, still more preferably 0.8 to 3 mass%, and further preferably 1 to 2 mass%. As one embodiment, when the total content of the α,β-unsaturated carboxylic acid and anhydride thereof in the acid-modified polyolefin resin (A) is in the range of 0.5 to 10 mass%, the flowability of the modified polyolefin resin composition becomes further good.

[0043] As one embodiment, a polyolefin resin derived from a living organism can be used instead of a polyolefin resin derived from petroleum as the polyolefin resin. The polyolefin resin derived from a living organism refers to a polyolefin resin produced from a biological resource (biomass). The biomass refers to a substance formed from an organic resource derived from a renewable biological source other than a fossil resource.

[0044] When the polyolefin resin derived from a living organism is used, the polyolefin resin preferably contains a propylene structural unit. When the polyolefin resin derived from a living organism is used, the biomass content of the polyolefin resin is usually 25% or more, preferably 27% or more, and more preferably 30% or more. The upper limit of the biomass content is 100% or less, and is not particularly limited. The biomass content of the polyolefin resin can be calculated, for example, from the carbon isotope content of mass number 14 determined according to ASTM D6866.

[0045] As the α,β-unsaturated carboxylic acid or anhydride thereof to be graft-polymerized with the polyolefin, for example, maleic acid, maleic anhydride, fumaric acid, citraconic acid, citraconic anhydride, mesaconic acid, itaconic acid, itaconic anhydride, aconitic acid, aconitic anhydride, nadic anhydride, and the like can be exemplified. Among these α,β-unsaturated carboxylic acids or anhydrides thereof, maleic acid, maleic anhydride, and itaconic anhydride are preferred, and maleic acid and maleic anhydride are more preferred.

[0046] As one embodiment, the acid value of the α,β-unsaturated carboxylic acid and anhydride component in the acid-modified polyolefin resin (A) is preferably 1 to 100 mgKOH / g, more preferably 5 to 50 mgKOH / g, still more preferably 10 to 40 mgKOH / g, and further preferably 15 to 30. When the acid value of the α,β-unsaturated carboxylic acid and anhydride component in the acid-modified polyolefin resin (A) is in the range of 1 to 100 mgKOH / g, the flowability of the modified polyolefin resin composition becomes further good.

[0047] The acid value of the α,β-unsaturated carboxylic acid and anhydride component in the acid-modified polyolefin resin (A) can be calculated by using a Fourier transform infrared spectrophotometer (FT-IR) to calculate the absorbance (I) of the stretching vibration peak (1780 cm -1 ) of the carbonyl (C=O) bond of succinic anhydride in the acid-modified polyolefin solution using the coefficient (f) obtained from a standard curve prepared from a chloroform solution of maleic anhydride by the following formula (i). Acid value (mgKOH / g) = [absorbance (I) x coefficient (f) x 2 x molecular weight of potassium hydroxide x 1000 (mg) / molecular weight of succinic anhydride]... Formula (i) In addition, in the above formula (i), the molecular weight of succinic anhydride is 100.07, and the molecular weight of potassium hydroxide is 56.11.

[0048] As the method of graft-polymerizing the polyolefin with the α,β-unsaturated carboxylic acid or anhydride thereof, a publicly known method can be widely employed. As such a method, for example, a method of heating and melting the polyolefin above the melting point in the presence of a radical initiator to react it with the α,β-unsaturated carboxylic acid or anhydride thereof (melt method); a method of dissolving the polyolefin in an organic solvent and heating and stirring it in the presence of a radical initiator to react it with the α,β-unsaturated carboxylic acid or anhydride thereof (solution method); and the like can be exemplified.

[0049] As one embodiment, the acid-modified polyolefin resin (A) can also be an acid-modified chlorinated polyolefin resin further subjected to chlorination. As the method of chlorination, for example, a method of blowing chlorine gas into the acid-modified polyolefin resin to introduce chlorine atoms can be exemplified. In more detail, the acid-modified polyolefin resin can be dispersed or dissolved in a solvent as needed, and then subjected to chlorination by blowing chlorine gas in the presence of a catalyst or under irradiation of ultraviolet rays, under pressure or at normal pressure (atmospheric pressure), at a temperature in the range of 50 to 150°C.

[0050] As the solvent used at the time of chlorination, for example, water, a chlorine-based solvent (e.g., chloroform, dichloromethane, carbon tetrachloride, etc.), and the like can be exemplified, and a chlorine-based solvent is preferred. The chlorine-based solvent can be removed by distillation under reduced pressure or the like at the end of chlorination, or can be replaced with another organic solvent.

[0051] As the catalyst used at the time of chlorination, for example, a radical initiator can be exemplified. As the radical initiator, for example, t-butyl peroxy-2-ethylhexanoate, t-butyl peroxyoctoate, di-t-butyl peroxide, dicumyl peroxide, and the like can be exemplified.

[0052] As one embodiment, the chlorine content in the acid-modified chlorinated polyolefin resin is preferably 5% by mass or more, more preferably 8% by mass or more, further preferably 10% by mass or more, particularly preferably 12% by mass or more, and most preferably 14% by mass or more, when the acid-modified polyolefin resin (A) is subjected to chlorination. When the chlorine content in the acid-modified chlorinated polyolefin resin is 5% by mass or more, the stability in solution becomes even better, and thus the acid-modified chlorinated polyolefin resin becomes easier to emulsify.

[0053] As one embodiment, the chlorine content in the acid-modified chlorinated polyolefin resin is preferably 40% by mass or less, more preferably 38% by mass or less, further preferably 35% by mass or less, particularly preferably 32% by mass or less, and most preferably 30% by mass or less, when the acid-modified polyolefin resin (A) is subjected to chlorination. When the chlorine content in the acid-modified chlorinated polyolefin resin is 40% by mass or less, the crystallinity of the acid-modified chlorinated polyolefin resin increases, and the adhesion to the polyolefin base material (particularly, a polypropylene base material) and the plastic material (particularly, PET and ABS) further improves.

[0054] As one embodiment, when the acid-modified polyolefin resin (A) is chlorinated, the chlorine content in the acid-modified chlorinated polyolefin resin is preferably 5% by mass or more, more preferably 8% by mass or more and 38% by mass or less, further more preferably 10% by mass or more and 35% by mass or less, further preferably 12% by mass or more and 32% by mass or less, particularly preferably 14% by mass or more and 30% by mass or less.

[0055] The chlorine content in the acid-modified chlorinated polyolefin resin can be measured according to JIS K-7229-1995. That is, the measurement is performed using the "oxygen flask combustion method" in which the acid-modified chlorinated polyolefin resin is combusted in an oxygen atmosphere, the generated chlorine gas is absorbed with water, and the amount is quantified by titration.

[0056] As one embodiment, the melting point of the acid-modified polyolefin resin (A) is preferably 90°C or lower, more preferably 85°C or lower, particularly preferably 80°C or lower. When the melting point of the acid-modified polyolefin resin (A) is 90°C or lower, the adhesion to the polyolefin base material (particularly, the polypropylene base material) becomes further good.

[0057] As one embodiment, the melting point of the acid-modified polyolefin resin (A) is preferably 50°C or higher, more preferably 55°C or higher, particularly preferably 60°C or higher. When the melting point of the acid-modified polyolefin resin (A) is 50°C or higher, the adhesion to the polyolefin base material (particularly, the polypropylene base material) becomes further good.

[0058] The melting point of the acid-modified polyolefin resin (A) can be measured by a differential scanning calorimeter (DSC) according to JIS K7121-2012. Specifically, using a DSC measuring device, after keeping a sample of about 5 mg in a heated molten state at 150°C for 10 minutes, the temperature is decreased at a rate of 10°C / minute, kept stable at -50°C, further increased at a rate of 10°C / minute to 150°C, and the melting peak temperature at the time of melting is measured, which is evaluated as the melting point.

[0059] As an embodiment, the weight average molecular weight (Mw) of the acid-modified polyolefin resin (A) is preferably 3000 to 200000, more preferably 10000 to 150000, further more preferably 20000 to 120000, further preferably 30000 to 100000, particularly preferably 40000 to 90000. When the weight average molecular weight (Mw) of the acid-modified polyolefin resin (A) is in the range of 3000 to 200000, the acid-modified polyolefin resin (A) has good flowability. In addition, when the weight average molecular weight (Mw) is in the range of 3000 to 200000, the cohesion of the acid-modified polyolefin resin (A) is further improved, and the adhesion to the polyolefin base material (particularly, the polypropylene base material) and the adhesion to the plastic material (particularly, PET and ABS) become further good. The weight average molecular weight (Mw) of the acid-modified polyolefin resin (A) can be measured by gel permeation chromatography (GPC). As for the specific measurement method, it is described in the Examples described below.

[0060] As an embodiment, the acid-modified polyolefin resin (A) can be further copolymerized with a radical polymerizable monomer, as long as the effect of the present application is not impaired. The content of the radical polymerizable monomer is usually 40 parts by mass or less, preferably 20 parts by mass or less, more preferably 5 parts by mass or less, further preferably 1 part by mass or less, relative to 100 parts by mass of the acid-modified polyolefin resin (A).

[0061] The form of the acid-modified polyolefin resin (A) when copolymerized with the radical polymerizable monomer is not limited, and as the form of copolymerization, for example, random copolymerization, block copolymerization, graft copolymerization (graft modification), and the like can be exemplified.

[0062] As the radical polymerizable monomer, for example, (meth)acrylic compounds, vinyl compounds, and the like can be exemplified. The (meth)acrylic compound refers to a compound containing at least one (meth)acryloyl group (acryloyl group and / or methacryloyl group) in the molecule.

[0063] As examples of the radical polymerizable monomer, (meth)acrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, cyclohexyl (meth)acrylate, hydroxyethyl (meth)acrylate, isobornyl (meth)acrylate, glycidyl (meth)acrylate, octyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, stearyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, acetoacetoxyethyl (meth)acrylate, N-methyl (meth)acrylamide, N-ethyl (meth)acrylamide, N-propyl (meth)acrylamide, N-isopropyl (meth)acrylamide, N-butyl (meth)acrylamide, N-isobutyl (meth)acrylamide, N-tert-butyl (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N,N-dimethylaminopropyl (meth)acrylamide, N,N-methylene-bis (meth)acrylamide, N-hydroxymethyl (meth)acrylamide, hydroxyethyl (meth)acrylamide, (meth)acryloyl morpholine, n-butyl vinyl ether, 4-hydroxybutyl vinyl ether, dodecyl vinyl ether, and the like can be given. Among these, methyl (meth)acrylate, ethyl (meth)acrylate, cyclohexyl (meth)acrylate, lauryl (meth)acrylate are preferred, and methacrylate esters thereof, i.e., methyl methacrylate (methyl methacrylate), ethyl methacrylate (ethyl methacrylate), cyclohexyl methacrylate (cyclohexyl methacrylate), lauryl methacrylate (lauryl methacrylate) are more preferred. The radical polymerizable monomers described above can be used individually or in combination of two or more.

[0064] As one embodiment, the content of the acid-modified polyolefin resin (A) is preferably 5 to 120 parts by mass, more preferably 10 to 90 parts by mass, more preferably 12.5 to 70 parts by mass, more preferably 15 to 50 parts by mass, further preferably 17.5 to 40 parts by mass, and particularly preferably 20 to 35 parts by mass, relative to 100 parts by mass of the compound (C) having a polymerizable unsaturated group.

[0065] As one embodiment, the proportion of the acid-modified polyolefin resin (A) is preferably 1 to 60% by mass, more preferably 4 to 50% by mass, further more preferably 7 to 40% by mass, further preferably 10 to 35% by mass, and particularly preferably 15 to 30% by mass, relative to the total mass of the modified polyolefin resin composition, in order to further maintain the flowability of the modified polyolefin resin composition and further improve the adhesion to the polyolefin base material (particularly, the polypropylene base material) and the adhesion to the plastic material (particularly, PET and ABS).

[0066] <Polyether amine (B)> The present application contains a polyether amine (B). The polyether amine (B) is generally a compound having a polyether chain and an amino group.

[0067] As one embodiment, the polyether amine (B) has a polyether chain, and preferably, the polyether chain contains at least one structure selected from the group consisting of a structure represented by Formula 1: -(O-CH2CH2)x- (in Formula 1, x is an integer of 2 to 120), a structure represented by Formula 2-1: -(O-CH2CH(CH3))y1- (in Formula 2-1, y1 is an integer of 2 to 90), a structure represented by Formula 2-2: -(O-CH2CH2CH2)y2- (in Formula 2-2, y2 is an integer of 2 to 90), a structure represented by Formula 3-1: -(O-CH2CH2CH2CH2)z1- (in Formula 3-1, z1 is an integer of 2 to 80), a structure represented by Formula 3-2: -(O-CH(CH3)CH2CH2)z2- (in Formula 3-2, z2 is an integer of 2 to 80), a structure represented by Formula 3-3: -(O-CH2CH(CH3)CH2)z3- (in Formula 3-3, z3 is an integer of 2 to 80), and a structure represented by Formula 3-4: -(O-CH2CH2CH(CH3))z4- (in Formula 3-4, z4 is an integer of 2 to 80).

[0068] As one embodiment, the polyether amine (B) has a polyether chain, and more preferably, the polyether chain contains at least one structure selected from the group consisting of a structure represented by Formula 1: -(O-CH2CH2)x- (in Formula 1, x is an integer of 2 to 120), a structure represented by Formula 2-1: -(O-CH2CH(CH3))y1- (in Formula 2-1, y1 is an integer of 2 to 90), and a structure represented by Formula 3-1: -(O-CH2CH2CH2CH2)z1- (in Formula 3-1, z1 is an integer of 2 to 80).

[0069] As one embodiment, more preferably, the polyether amine (B) is a compound represented by the following Formula 1A. R 1 -(O-R 2 )a-R 3 Formula 1A (In Formula 1A: R 1 and R 3 each independently represent an amino group or a linear or branched alkyl group having 1 to 10 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, or 10) which can have an amino group. R 2 represents a linear or branched alkylene group having 2 to 4 carbon atoms (2, 3, or 4). a is an integer of 1 to 120.

[0070] In the above Formula 1A, as the alkyl group having 1 to 10 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, or 10), for example, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a t-butyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, and the like can be exemplified.

[0071] In the above Formula 1A, the linear or branched alkylene group having 2 to 4 carbon atoms (2, 3, or 4) is preferably an ethylene group (-CH2CH2-), a methyl ethylene group (-CH2CH(CH3)-), an n-propylene group (-CH2CH2CH2-), a 1-methyl propylene group (-CH(CH3)CH2CH2-), a 2-methyl propylene group (-CH2CH(CH3)CH2-), a 3-methyl propylene group (-CH2CH2CH(CH3)-), or an n-butylene group (-CH2CH2CH2CH2-).

[0072] In the above Formula 1A, preferably, R 1 represents a linear or branched alkyl group having 1 to 10 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, or 10), R 2 represents a linear or branched alkylene group having 2 to 4 carbon atoms (2, 3, or 4), R 3 represents an amino group, and a is an integer of 1 to 120.

[0073] As one embodiment, from the viewpoint of stably dissolving and / or dispersing the acid-modified polyolefin resin (A) in a compound (C) having polymerizable unsaturated groups, the polyetheramine (B) preferably has a primary or secondary amino group at one end, and the weight-average molecular weight (Mw) of the polyetheramine (B) is 200 to 50,000. As one embodiment, the polyetheramine (B) is more preferably having a primary or secondary amino group at one end, and the weight-average molecular weight (Mw) of the polyetheramine (B) is 300 to 10,000. As one embodiment, the polyetheramine (B) is even more preferably having a primary amino group at one end, and the weight-average molecular weight (Mw) of the polyetheramine (B) is 500 to 5,000.

[0074] As one embodiment, the weight-average molecular weight (Mw) of polyetheramine (B) is typically 200 to 50,000, preferably 300 to 20,000, more preferably 350 to 10,000, further preferably 450 to 7,000, and particularly preferably 500 to 5,000.

[0075] As one embodiment, the weight-average molecular weight (Mw) of polyetheramine (B) can be determined by GPC and converted from the standard curve of polystyrene. Furthermore, the GPC determination uses THF or similar solvents and is performed using commercially available equipment and conventionally known methods.

[0076] As one embodiment, the polyetheramine (B) preferably has an HLB value of 2 to 20, more preferably 5 to 19, and even more preferably 8 to 18. When the HLB value is in the range of 2 to 20, the flowability of the modified polyolefin resin composition can be maintained better.

[0077] The HLB value is a value that indicates the degree of hydrophilicity or lipophilicity (hydrophobicity) of polyetheramine (B). The HLB value is calculated using the Griffin method. In the Griffin method, the HLB value is calculated based on the following equation 4. HLB value = 20 × total formula weight of hydrophilic groups / molecular weight ... Equation 4

[0078] As one embodiment, the polyetheramine (B) can be bonded to the acid-modified polyolefin resin (A) through various reaction mechanisms. Examples of such reaction mechanisms include, for instance, reactions that form covalent and / or ionic bonds. More specifically, examples include, for instance, amidation reactions of carboxylic anhydride groups with primary or secondary amino groups, imidization reactions, and neutralization reactions of carboxylic acid groups with primary or secondary amino groups.

[0079] As polyetheramine (B), commercially available products are widely used. Examples of commercially available polyetheramine (B) products include, for instance, the following products manufactured by HUNTSMAN Corporation. "JEFFAMINE M-600 (MW=600, HLB value=2.1)" "JEFFAMINE M-1000 (MW=1000, HLB value=16.1)" “JEFFAMINE M-2005 (MW=2000, HLB value=2.7)” "JEFFAMINE M-2070 (MW=2000, HLB value=13.8)" "JEFFAMINE M-3085 (MW=3000, HLB value=16.8)" "JEFFAMINE D-230 (MW=230, HLB value=3.6)" "JEFFAMINE D-400 (MW=430, HLB value=1.7)" “JEFFAMINE D-2000 (MW=2000, HLB value=0.3)” "JEFFAMINE D-4000 (MW=4000, HLB value=0.2)" "JEFFAMINE ED-600 (MW=600, HLB value=13.4)", "JEFFAMINE ED-900 (MW=900, HLB value=12.5)", "JEFFAMINE ED-2003 (MW=2000, HLB value=16.7)" etc. These commercially available products can be used individually or in combination of two or more.

[0080] As one embodiment, in order to further maintain the flowability of the modified polyolefin resin composition and to further improve the adhesion to polyolefin substrates (especially polypropylene substrates) and plastic materials (especially PET and ABS), the content of polyetheramine (B) is typically 6 to 100 parts by weight relative to 100 parts by weight of acid-modified polyolefin resin (A), preferably 10 to 90 parts by weight, more preferably 15 to 80 parts by weight, even more preferably 20 to 70 parts by weight, even more preferably 25 to 60 parts by weight, and particularly preferably 30 to 50 parts by weight.

[0081] As one embodiment, the content ratio of the polyetheramine (B) is usually 0.5 to 40% by mass, preferably 1 to 35% by mass, more preferably 2 to 30% by mass, further more preferably 3 to 25% by mass, further preferably 4 to 20% by mass, and particularly preferably 5 to 17.5% by mass, relative to the total mass of the modified polyolefin resin composition, in order to further favorably maintain the flowability of the modified polyolefin resin composition and further improve the adhesion to the polyolefin base material (particularly, the polypropylene base material) and the adhesion to the plastic material (particularly, PET and ABS).

[0082] <Compound (C) having a polymerizable unsaturated group> The present application contains a compound (C) having a polymerizable unsaturated group. The compound (C) having a polymerizable unsaturated group generally has one or more (for example, one, two, three, or four) polymerizable unsaturated groups. In the present specification, the polymerizable unsaturated group means an unsaturated group capable of undergoing radical polymerization.

[0083] As one embodiment, the number of the polymerizable unsaturated groups in the compound (C) having a polymerizable unsaturated group is preferably one or two.

[0084] As one embodiment, the polymerizable unsaturated group in the compound (C) having a polymerizable unsaturated group is preferably at least one selected from the group of an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, a vinyl group, an allyl group, a propenyl group, an isopropenyl group, a maleimide group, and a vinyl ether group.

[0085] As one embodiment, the polymerizable unsaturated group in the compound (C) having a polymerizable unsaturated group is more preferably at least one selected from the group of an acryloyl group, a methacryloyl group, an acryloyloxy group, and a methacryloyloxy group.

[0086] As one embodiment, the polymerizable unsaturated group in the compound (C) having a polymerizable unsaturated group is further more preferably an acryloyloxy group and / or a methacryloyloxy group.

[0087] As one embodiment, the compound (C) having a polymerizable unsaturated group preferably contains a compound having a hydroxyl group and one or more (for example, one, two, three, or four) polymerizable unsaturated groups. In this case, the number of the hydroxyl groups is preferably one or two, and more preferably one.

[0088] As one embodiment, the compound (C) having a polymerizable unsaturated group more preferably contains a compound having a hydroxyl group and one to three (one, two, or three) polymerizable unsaturated groups. In this case, the number of the hydroxyl groups is preferably one or two, and more preferably one.

[0089] As one embodiment, the compound (C) having a polymerizable unsaturated group preferably contains a compound having a linear or branched alkyl group having an oxygen alkylene group and / or 1 to 20 (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) carbon atoms, and 1 or more (for example, 1, 2, 3, or 4) polymerizable unsaturated groups. In this case, the number of polymerizable unsaturated groups is preferably 1 or 2, more preferably 2.

[0090] As one embodiment, the compound (C) having a polymerizable unsaturated group preferably contains a compound having a linear or branched alkyl group having an oxygen alkylene group and / or 1 to 20 (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) carbon atoms, and 1 or more (for example, 1, 2, 3, or 4) polymerizable unsaturated groups. In this case, the number of polymerizable unsaturated groups is preferably 1 or 2, more preferably 2.

[0091] As one embodiment, the compound (C) having a polymerizable unsaturated group preferably contains a compound having a linear or branched alkyl group having an oxygen alkylene group and / or 1 to 20 (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) carbon atoms, and 1 or more (for example, 1, 2, 3, or 4) polymerizable unsaturated groups. In this case, the number of polymerizable unsaturated groups is preferably 1 or 2, more preferably 2.

[0092] As one embodiment, the compound (C) having a polymerizable unsaturated group more preferably contains a compound having a linear or branched alkyl group having an oxygen alkylene group and / or 1 to 20 (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) carbon atoms, and 1 or 2 polymerizable unsaturated groups.

[0093] As one embodiment, the oxygen alkylene group is generally a structure represented by the following Formula 5. -(Y 1 -O)m- Formula 5 [In Formula 5: Y 1 represents a linear or branched alkylene group having 1 to 10 (1, 2, 3, 4, 5, 6, 7, 8, 9, or 10) carbon atoms. m is an integer of 1 to 20

[0094] In the above Formula 5, Y 1 is preferably a linear or branched alkylene group having 1 to 5 carbon atoms (1, 2, 3, 4, or 5).

[0095] In the above Formula 5, m is preferably an integer of 2 to 15.

[0096] As one embodiment, the compound (C) having a polymerizable unsaturated group preferably contains a compound represented by the following Formula 6. R a -R b -R c Formula 6 [In Formula 6: R a represents a polymerizable unsaturated group. R c represents a polymerizable unsaturated group or a methyl group. R b represents a group represented by -(Y 2 -O)n- represents, or a linear or branched alkylene group having 1 to 20 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20). Y 2 represents a linear or branched alkylene group having 1 to 10 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, or 10). n is an integer of 1 to 20.

[0097] In the above Formula 6, Y 2 is preferably a linear or branched alkylene group having 1 to 5 carbon atoms (1, 2, 3, 4, or 5).

[0098] In the above Formula 6, n is preferably an integer of 2 to 15.

[0099] As one embodiment, the compound (C) having a polymerizable unsaturated group more preferably contains one or two or more kinds of the compound represented by the above Formula 6.

[0100] As one embodiment, the compound (C) having a polymerizable unsaturated group preferably contains a compound having a (meth)acryloyloxy group as the polymerizable unsaturated group. As the compound having a (meth)acryloyloxy group, for example, a compound having one (meth)acryloyloxy group, a compound having two (meth)acryloyloxy groups, a compound having three or more (meth)acryloyloxy groups, and the like can be exemplified. These compounds can be used individually or two or more kinds thereof can be used in combination.

[0101] As the compound having one (meth)acryloyloxy group, for example, a compound represented by the following Formula 7 can be exemplified. (meth)acrylic acid-2-hydroxyethyl ester, (meth)acrylic acid-2-hydroxypropyl ester, (meth)acrylic acid-3-hydroxypropyl ester, (meth)acrylic acid-4-hydroxybutyl ester, 1,4-cyclohexanedimethanol mono(meth)acrylate, polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, polytetramethylene glycol mono(meth)acrylate, polyethylene glycol polypropylene glycol mono(meth)acrylate, (meth)acrylic acid-2-hydroxy-3-phenoxypropyl ester, phenoxydiethylene glycol (meth)acrylate, 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-hexyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, stearyl (meth)acrylate, behenyl (meth)acrylate, and the like (meth)acrylic acid alkyl esters; (meth)acrylic acid cyclohexyl ester, (meth)acrylic acid isobornyl ester, and the like (meth)acrylic acid esters having an alicyclic structure; (meth)acrylic acid benzyl ester, phenoxyethyl acrylate, phenoxyethyl methacrylate, and the like (meth)acrylic acid esters having an aromatic ring; (meth)acrylic acid dimethylaminoethyl ester, (meth)acrylic acid diethylaminoethyl ester, (meth)acrylic acid t-butylaminoethyl ester, (meth)acrylic acid methylethylaminoethyl ester, dimethylaminostyrene, diethylaminostyrene, (meth)acrylic acid pentamethylpiperidyl ester, (meth)acrylic acid tetramethylpiperidyl ester, and the like (meth)acrylic acid esters having an amino group; (meth)acrylic acid glycidyl ester, (meth)acrylic acid-3,4-epoxycyclohexyl ester, and the like (meth)acrylic acid esters containing an epoxy group; (meth)acrylic acid methoxy methyl ester, (meth)acrylic acid ethoxy methyl ester, (meth)acrylic acid propoxy methyl ester, (meth)acrylic acid-2-methoxyethyl ester, (meth)acrylic acid-1-methoxyethyl ester, (meth)acrylic acid-2-ethoxyethyl ester, (meth)acrylic acid-1-ethoxyethyl ester, (meth)acrylic acid-2-propoxyethyl ester, (meth)acrylic acid-2-isopropoxyethyl ester, and the like (meth)acrylic acid esters containing an ether group, and the like. These compounds can be used individually or in combination of two or more.

[0102] As the compound having two (meth)acryloyloxy groups, for example, the following can be given: 1,4-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, and the like alkylene glycol di(meth)acrylates; Bisphenol A ethylene oxide-modified di(meth)acrylate, bisphenol F ethylene oxide-modified di(meth)acrylate, and the like bisphenol-modified di(meth)acrylates; Ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, urethane di(meth)acrylate, epoxy di(meth)acrylate, glycerol di(meth)acrylate, and the like. These compounds can be used individually or in combination of two or more.

[0103] As the compound having three or more (meth)acryloyloxy groups, for example, the following can be mentioned: Dipentaerythritol hexa(meth)acrylate, pentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, trimethylolpropane tri(meth)acrylate; Ethylene oxide-modified dipentaerythritol hexa(meth)acrylate, ethylene oxide-modified pentaerythritol tetra(meth)acrylate, and the like ethylene oxide-modified (meth)acrylates; Ethylene oxide-modified dipentaerythritol hexa(meth)acrylate, ethylene oxide-modified pentaerythritol tetra(meth)acrylate, and the like ethylene oxide-modified (meth)acrylates; Pentaerythritol tri(meth)acrylate hexamethylene diisocyanate urethane prepolymer, pentaerythritol tri(meth)acrylate toluene diisocyanate urethane prepolymer, dipentaerythritol penta(meth)acrylate hexamethylene diisocyanate urethane prepolymer, and the like urethane methacrylates. These compounds can be used individually or in combination of two or more.

[0104] As one embodiment, from the viewpoint of stably dissolving and / or dispersing the acid-modified polyolefin resin (A) in the compound having a polymerizable unsaturated group (C) and the viewpoint of suppressing the agglomerates, the compound having a polymerizable unsaturated group (C) is more preferably a compound having two (meth)acryloyloxy groups.

[0105] As the compound having two (meth)acryloyloxy groups, at least one selected from the group of neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate, and polypropylene glycol di(meth)acrylate is preferable.

[0106] As specific examples of the compound (C) having a polymerizable unsaturated group, in addition to the above, there can be mentioned (meth)acrylamide, N-methoxymethyl- (meth)acrylamide, N-ethoxymethyl- (meth)acrylamide, N-propoxymethyl- (meth)acrylamide, N-butoxymethyl- (meth)acrylamide, N-pentoxymethyl- (meth)acrylamide, N,N-di(methoxymethyl)acrylamide, N-ethoxymethyl-N-methoxymethylmethacrylamide, N,N-di(ethoxymethyl)acrylamide, N-ethoxymethyl-N-propoxymethylmethacrylamide, N,N-di(propoxymethyl)acrylamide, N-butoxymethyl-N- (propoxymethyl) methacrylamide, N,N-di(butoxymethyl)acrylamide, N-butoxymethyl-N- (methoxymethyl) methacrylamide, N,N-dipentoxymethylacrylamide, N-methoxymethyl-N- (pentoxymethyl) methacrylamide, N,N-dimethylaminopropylacrylamide, N,N-diethylaminopropylacrylamide, N,N-dimethylacrylamide, N,N-diethylacrylamide, diacetonemethacrylamide, and the like compounds having an amide group; styrene, α-methylstyrene, o-methylstyrene, p-methylstyrene, m-methylstyrene, vinyl naphthalene, indene, and the like aromatic vinyl compounds; (meth)acrylonitrile, acryloyl morpholine, and the like.

[0107] As one embodiment, from the viewpoint of further favorably maintaining the flowability of the modified polyolefin resin composition and further favorably improving the adhesion to the polyolefin base material (particularly, polypropylene base material) and the plastic material (particularly, PET and ABS), the content ratio of the compound (C) having a polymerizable unsaturated group is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, still more preferably 30 to 85% by mass, and further preferably 40 to 80% by mass, with respect to the total mass of the modified polyolefin resin composition.

[0108] As one embodiment, the compound (C) having a polymerizable unsaturated group preferably contains a compound having a hydroxyl group and one or more (e.g., one, two, three, or four) polymerizable unsaturated groups, from the viewpoint of further favorably maintaining the flowability of the modified polyolefin resin composition and further favorably improving the adhesion to polyolefin substrates (particularly, polypropylene substrates) and plastic materials (particularly, PET and ABS). In this case, the proportion of the compound having a hydroxyl group and one or more (e.g., one, two, three, or four) polymerizable unsaturated groups, relative to the total mass of the modified polyolefin resin composition, is preferably 1 to 50% by mass, more preferably 3 to 45% by mass, still more preferably 6 to 40% by mass, and further preferably 10 to 35% by mass, from the viewpoint of further favorably maintaining the flowability of the modified polyolefin resin composition and further favorably improving the adhesion to polyolefin substrates (particularly, polypropylene substrates) and plastic materials (particularly, PET and ABS).

[0109] Specific examples of the compound having a hydroxyl group and one or more (e.g., one, two, three, or four) polymerizable unsaturated groups include 2-hydroxy-1,3-dimethylacryloxypropane, 2-hydroxy-3-methacryloylpropyl acrylate, glycerol diacrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, and the like.

[0110] As one embodiment, the compound (C) having a polymerizable unsaturated group can also contain a (meth)acrylic monomer component derived from biomass. The (meth)acrylic monomer component derived from biomass refers to a substance composed of a (meth)acrylic acid derived from biomass, or an ester of an alkyl alcohol derived from biomass and a (meth)acrylic acid derived from biomass or not derived from biomass. Examples of the alkyl alcohol derived from biomass include biomass ethanol, an alkyl alcohol derived from palm oil or palm kernel oil, coconut oil, and the like. When the number of carbon atoms of the alkyl alcohol derived from biomass is three or more, the alkyl alcohol can be linear or can have a branched chain.

[0111] As one embodiment, the weight average molecular weight (Mw) of the compound (C) having a polymerizable unsaturated group is preferably 5,000 or less, more preferably 2,000 or less, and still more preferably 1,000 or less, from the viewpoint of further favorably maintaining the flowability of the modified polyolefin resin composition and further improving the handling properties.

[0112] As one embodiment, the weight average molecular weight (Mw) of the compound (C) having a polymerizable unsaturated group is preferably 100 or more, more preferably 120 or more, and still more preferably 140 or more, from the viewpoint of further favorably maintaining the flowability of the modified polyolefin resin composition and further improving the handling properties.

[0113] As one embodiment, the weight average molecular weight (Mw) of the compound (C) having a polymerizable unsaturated group is preferably 100 or more and 5000 or less, more preferably 120 or more and 2000 or less, and still more preferably 140 or more and 1000 or less, from the viewpoint of further maintaining the fluidity of the modified polyolefin resin composition and further improving the handling property.

[0114] As one embodiment, the modified polyolefin resin composition can further contain a resin for forming a coating film other than the compound (C) having a polymerizable unsaturated group. As the resin for forming a coating film, for example, an acrylic resin, a polyester resin, an alkyd resin, a polyether resin, a polyolefin resin, a polyurethane resin, a polycarbonate resin, a melamine resin, an epoxy resin, a carbodiimide resin, or the like can be exemplified. These resins can be used alone or in combination of two or more. The content of the above-mentioned resin for forming a coating film is preferably 10 to 30 parts by mass with respect to 100 parts by mass of the modified polyolefin resin composition.

[0115] <IONIC LIQUID (D)> As one embodiment, the ionic liquid (D) is composed of a cation and an anion. In the present specification, the ionic liquid (D) refers to a salt which is usually in a liquid state at 100°C or lower. In the present specification, the ionic liquid (D) refers to a salt which is preferably in a liquid state at 25°C.

[0116] As one embodiment, as the ionic liquid (D), a substance in which a cation and an anion are appropriately combined can be used.

[0117] As the cation constituting the ionic liquid (D), for example, a cation having a positively charged nitrogen atom, a cation having a positively charged phosphorus atom, a cation having a positively charged sulfur atom, a cation having a positively charged nitrogen atom and a sulfur atom, a cation having a positively charged metal element, or the like can be exemplified. The cation constituting the ionic liquid (D) is preferably a cation having a positively charged nitrogen atom, a cation having a positively charged phosphorus atom, or a cation having a positively charged sulfur atom, and more preferably a cation having a positively charged nitrogen atom.

[0118] As the cation having a positively charged nitrogen atom, for example, an imidazolium cation, an ammonium cation, a pyridinium cation, a quinolinium cation, a pyrrolidinium cation, a piperidinium cation, a piperazinium cation, a morpholinium cation, a pyridazinium cation, a pyrimidinium cation, a pyrazinium cation, a pyrazolinium cation, a thiazolium cation, an oxazolium cation, a triazolium cation, a guanidinium cation, a 4-aza-1-azonium bicyclo[2,2,2]octane cation, or the like can be exemplified. In addition, these cations can also have one or more substituents at an arbitrary position. As the substituent, for example, an alkyl group or the like can be exemplified.

[0119] As specific examples of the imidazolium cation, there can be mentioned 1-methylimidazolium cation, 1-ethylimidazolium cation, 1-propylimidazolium cation, 1-butylimidazolium cation, 1-butyl-3-methylimidazolium cation, 1-ethyl-3-methylimidazolium cation, 1-allyl-3-methylimidazolium cation, 1,3-diallylimidazolium cation, 1-benzyl-3-methylimidazolium cation, 1-methyl-3-octylimidazolium cation, 1-ethyl-2,3-dimethylimidazolium cation, 1-butyl-2,3-dimethylimidazolium cation, 1,2-dimethyl-3-propylimidazolium cation and the like 1,2,3-trialkylimidazolium cations; 1-cyanopropyl-3-methylimidazolium cation, 1,3-bis(cyanomethyl)imidazolium cation, 1,3-bis(3-cyanopropyl)imidazolium cation, 1-(2-hydroxyethyl)-3-methylimidazolium cation, 1-methoxyethyl-3-methylimidazolium cation, 1-[2-(2-methoxyethoxy)-ethyl]-3-methylimidazolium cation, 1,3-diethoxyimidazolium cation, 1,3-dimethoxyimidazolium cation, 1,3-dihydroxyimidazolium cation, 1-methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylimidazolium cation, 1-methyl-3-[(triethoxysilyl)propyl]imidazolium cation and the like.

[0120] As specific examples of the ammonium cation, there can be mentioned dioctylammonium cation, bis(2-ethylhexyl)ammonium cation and the like dialkylammonium cations, trioctylammonium cation, dimethylmyristylammonium cation, dimethylpalmitylammonium cation, dimethylstearylammonium cation, dimethylbehenylammonium cation, dilaurylmethylammonium cation and the like trialkylammonium cations; methyltrioctylammonium cation, trihexyltetradecylammonium cation, (2-hydroxyethyl)trimethylammonium cation, (2-acryloyloxyethyl)trimethylammonium cation, (2-methacryloyloxyethyl)trimethylammonium cation, N,N-diethyl-N-(2-methoxyethyl)-N-methylammonium cation, tris(2-hydroxyethyl)methylammonium cation, trimethyl(1H,1H,2H,2H-heptadecafluorodecyl)ammonium cation, 2-(methacryloyloxy)ethyltrimethylammonium cation and the like tetraalkylammonium cations; dibenzylammonium cation and the like diarylammonium cations; tribenzylammonium cation and the like triarylammonium cations and the like. Among these, the ammonium cation is preferably a tetraalkylammonium.

[0121] As specific examples of the pyridinium cation, there can be mentioned 1- ethylpyridinium cation, 1-butylpyridinium cation, 1-(3-hydroxypropyl)pyridinium cation, 1- ethyl-3-methylpyridinium cation, 1-butyl-3-methylpyridinium cation, 1-butyl-4- methylpyridinium cation, 1-(3-cyanopropyl)pyridinium cation, and the like.

[0122] As specific examples of the pyrrolidinium cation, there can be mentioned 1- methyl-1-propylpyrrolidinium cation, 1-butyl-1-methylpyrrolidinium cation, 1-(2- hydroxyethyl)-1-methylpyrrolidinium cation, 1-ethyl-1-methylpyrrolidinium cation, and the like.

[0123] As specific examples of the pyrrolidinium cation, there can be mentioned 1- methyl-1-propylpyrrolidinium cation, 1-butyl-1-methylpyrrolidinium cation, 1-(2- hydroxyethyl)-1-methylpyrrolidinium cation, 1-ethyl-1-methylpyrrolidinium cation, and the like.

[0124] Cations having a phosphorus atom with a positive charge are generally referred to as phosphonium cations. As specific examples of the cation having a phosphorus atom with a positive charge, there can be mentioned tetrabutylphosphonium cation, tetrahexylphosphonium cation, trihexyltetradecylphosphonium cation, triphenylmethylphosphonium cation, (2-cyanoethyl)triethylphosphonium cation, (3-chloropropyl)trioctylphosphonium cation, tributyl(4-vinylbenzyl)phosphonium cation, triisobutylmethylphosphonium cation, triethylmethylphosphonium cation, tributylmethylphosphonium cation, tributylhexadecylphosphonium cation, 3- (triphenylphosphonio)propane-1-sulfonic acid cation, and the like.

[0125] Cations having a sulfur atom with a positive charge are generally referred to as sulfonium cations. As specific examples of the cation having a sulfur atom with a positive charge, there can be mentioned triethylsulfonium cation, tributylsulfonium cation, 1- ethyltetrahydrothiophenium cation, 1-butyltetrahydrothiophenium cation, and the like.

[0126] As one embodiment, from the viewpoint of further favorably maintaining the fluidity, the viewpoint of further improving the adhesion to the polyolefin base material (particularly, polypropylene base material) and the plastic material (particularly, PET and ABS), and the viewpoint of further improving the antistatic property, the cation constituting the ionic liquid (D) is preferably at least one cation selected from the group of tetraalkylammonium cation, imidazolium cation, pyridinium cation, pyrazolium cation, pyrrole cation, pyrrolinium cation, pyrrolidinium cation, and piperidinium cation, and more preferably tetraalkylammonium cation.

[0127] As one embodiment, the cation constituting the ionic liquid (D) is preferably a cation having a polymerizable unsaturated group from the viewpoint of further favorably maintaining fluidity, the viewpoint of further improving adhesion to polyolefin substrates (particularly polypropylene substrates) and plastic materials (particularly PET and ABS), and the viewpoint of further improving antistatic properties.

[0128] As specific examples of the cation having a polymerizable unsaturated group, (2-acryloyloxyethyl)trimethylammonium cation, (2-methacryloyloxyethyl)trimethylammonium cation, and the like can be given.

[0129] As one embodiment, the cation constituting the ionic liquid (D) is preferably a tetraalkylammonium cation and a tetraalkylammonium cation having one or two polymerizable unsaturated groups, and more preferably a tetraalkylammonium cation and a tetraalkylammonium cation having one polymerizable unsaturated group.

[0130] As one embodiment, the polymerizable unsaturated group possessed by the cation constituting the ionic liquid (D) is preferably an acryloyl group, a methacryloyl group, an acryloyloxy group, or a methacryloyloxy group, more preferably an acryloyloxy group or a methacryloyloxy group, and still more preferably an acryloyloxy group. The number of the polymerizable unsaturated groups possessed by the cation is preferably one or two, and more preferably one.

[0131] As one embodiment, the anion constituting the ionic liquid (D) is preferably a sulfonic acid anion, a carboxylic acid anion, a phosphoric acid anion, a sulfonamide anion, or a sulfonimide anion, and more preferably a sulfonimide anion.

[0132] As specific examples of the sulfonimide anion, bis(fluorosulfonyl)imide anion, bis(trifluoromethanesulfonyl)imide anion, bis(pentafluoroethanesulfonyl)imide anion, bis(heptafluoropropylsulfonyl)imide anion, bis(nonafluorobutylsulfonyl)imide anion, [(trifluoromethanesulfonyl)(pentafluoroethanesulfonyl)]imide anion, and the like can be given.

[0133] As specific examples of the anion constituting the ionic liquid (D), there can be mentioned fluoride ion, chloride ion, bromide ion, iodide ion, dicyanamide ion, bis(fluorosulfonyl)imide ion, bis(trifluoromethylsulfonyl)imide ion, 2,2,2-trifluoro-N- (trifluoromethylsulfonyl)acetamide ion, bis(pentafluoroethylsulfonyl)imide ion, bis(nonafluorobutylsulfonyl)imide ion, tetrafluoroborate ion, tetra[3,5-bis(trifluoromethyl)phenyl]borate ion, methanesulfonate ion, butanesulfonate ion, trifluoromethanesulfonate ion, tetrafluoroethanesulfonate ion, nonafluorobutanesulfonate ion, benzenesulfonate ion, p-toluenesulfonate ion, 2,4,6-trimethylbenzenesulfonate ion, styrenesulfonate ion, perfluorooctanesulfonate ion, heptadecafluorooctanesulfonate ion, 3-methacryloyloxypropylsulfonate ion, 3-acryloyloxypropylsulfonate ion, methylsulfate ion, ethylsulfate ion, octylsulfate ion, diethyleneglycol monomethyl ether sulfate ion, hydrogen sulfate ion, hexafluorophosphate ion, tris(pentafluoroethyl)trifluorophosphate ion, dihydrogen phosphate ion, dibutyl phosphate ion, diethyl phosphate ion, dimethyl phosphate ion, bis(2,4,4-trimethylpentyl)phosphonate ion, methylphosphonate ion, methyl methylphosphonate ion, formate ion, acetate ion, propionate ion, butyrate ion, trifluoroacetate ion, glycolate ion, perfluorononanoate ion, decanoate ion, mandelate ion, thiosalicylate ion, benzoate ion, salicylate ion, p-methylbenzoate ion, p-nitrobenzoate ion, fluorohydrogenate ion, lactate ion, glycinate ion, alaninate ion, leucinate ion, valinate ion, trifluoromethylsulfonyl leucinate ion, trifluoromethylsulfonyl valinate ion, nitrate ion, perchlorate ion, phenoxy ion, thiocyanate ion, tris(trifluoromethylsulfonyl)methide ion, acetylsulfamate ion, saccharinate ion, pyrazolynate ion, imidazolate ion, thiazolate ion, triazolate ion, tetrazolate ion, indazolate ion, benzothiazolate ion, hexafluoroarsenate ion, hexafluoroantimonate ion, thiocyanate ion, tetrachloroaluminate ion, tetrachloroferrate ion, carbonate ion, methylcarbonate ion, carbamate ion, and the like.

[0134] As specific examples of the ionic liquid (D), the following can be given: tetrahexylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N-ethyl-N-propylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N-ethyl-n-butylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N-ethyl-N-pentylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N-ethyl-N-hexylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N-ethyl-N-heptylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N-ethyl-N-nonylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N,N-dipropylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N-propyl-n-butylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N-propyl-N-pentylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N-propyl-N-hexylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N-propyl-N-heptylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-n-butyl-N-hexylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-n-butyl-N-heptylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N-pentyl-N-hexylammonium bis(trifluoromethylsulfonyl)imide, N,N-dimethyl-N,N-dihexylammonium bis(trifluoromethylsulfonyl)imide, trimethylheptylammonium bis(trifluoromethylsulfonyl)imide, N,N-diethyl-N-methyl-N-propylammonium bis(trifluoromethylsulfonyl)imide, N,N-diethyl-N-methyl-N-pentylammonium bis(trifluoromethylsulfonyl)imide, N,N-diethyl-N-methyl-N-heptylammonium bis(trifluoromethylsulfonyl)imide, N,N-diethyl-N-propyl-N-pentylammonium bis(trifluoromethylsulfonyl)imide, N,N-dipropyl-N-methyl-N-ethylammonium bis(trifluoromethylsulfonyl)imide, N,N-dipropyl-N-methyl-N-pentylammonium bis(trifluoromethylsulfonyl)imide, N,N-dipropyl-n-butyl-N-hexylammonium bis(trifluoromethylsulfonyl)imide, triethylpropylammonium bis(trifluoromethylsulfonyl)imide, triethylpentylammonium bis(trifluoromethylsulfonyl)imide, triethylheptylammonium bis(trifluoromethylsulfonyl)imide, N,N-dipropyl-N,N-dihexylammonium bis(trifluoromethylsulfonyl)imide, N,N-dibutyl-N-methyl-N-pentylammonium bis(trifluoromethylsulfonyl)imide, N,N-dibutyl-N-methyl-N-hexylammonium bis(trifluoromethylsulfonyl)imide, trioctylmethylammonium bis(trifluoromethylsulfonyl)imide, N-methyl-N-ethyl-N-propyl-N-pentylammonium bis(trifluoromethylsulfonyl)imide, (2-acryloyloxyethyl)trimethylammonium bis(trifluoromethylsulfonyl)imide, methyltrioctylammonium bis(trifluoromethylsulfonyl)imide, trioctylammonium salicylate, dioctylammonium benzoate, dioctylammonium-4-methylbenzoate, dioctylammonium-4-nitrobenzoate, dioctylammonium salicylate, bis(2-ethylhexyl)ammonium benzoate, bis(2-ethylhexyl)ammonium-4-methylbenzoate, bis(2-ethylhexyl)ammonium-4-nitrobenzoate, bis(2-ethylhexyl)ammonium salicylate, trioctylammonium benzoate, trioctylammonium-4-methylbenzoate, trioctylammonium-4-nitrobenzoate, dimethylmyristylammonium benzoate, dimethylmyristylammonium-4-methylbenzoate, dimethylmyristylammonium-4-nitrobenzoate, dimethylmyristylammonium salicylate, dimethylpalmitylammonium benzoate, dimethylpalmitylammonium-4-methylbenzoate, dimethylpalmitylammonium-4-nitrobenzoate, dimethylpalmitylammonium salicylate, dimethylstearylammonium benzoate, dimethylstearylammonium-4-methylbenzoate, dimethylstearylammonium-4-nitrobenzoate, dimethylstearylammonium salicylate, dimethylbehenylammonium benzoate, dimethylbehenylammonium-4-methylbenzoate, dimethylbehenylammonium-4-nitrobenzoate, dimethylbehenylammonium salicylate, dilaurylmethylammonium benzoate, dilaurylmethylammonium-4-methylbenzoate, dilaurylmethylammonium-4-nitrobenzoate, dilaurylmethylammonium salicylate, dibenzylammonium benzoate, dibenzylammonium-4-methylbenzoate, dibenzylammonium-4-nitrobenzoate, dibenzylammonium salicylate, tribenzylammonium benzoate, tribenzylammonium-4-methylbenzoate, tribenzylammonium-4-nitrobenzoate, tribenzylammonium salicylate, and the like.

[0135] As the ionic liquid (D), (2-acryloyloxyethyl)trimethylammonium bis(trifluoromethylsulfonyl)imide and methyltrioctylammonium bis(trifluoromethylsulfonyl)imide are particularly preferable.

[0136] As one embodiment, the content of the ionic liquid (D) is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, and further preferably 0.8 to 12.5 parts by mass, relative to 100 parts by mass of the modified polyolefin resin composition. By making the content of the ionic liquid (D) within the above range, the antistatic property is further improved, the adhesion to polyolefin substrates (particularly polypropylene substrates) and plastic materials (particularly PET and ABS) is further improved, and the flowability of the modified polyolefin resin composition tends to be further improved.

[0137] As a preferable mode (hereinafter, referred to as "Mode A") of the modified polyolefin resin composition, the following substances can be exemplified: The modified polyolefin resin composition contains an acid-modified polyolefin resin (A), a polyetheramine (B), two kinds of compounds having a polymerizable unsaturated group (C), and an ionic liquid (D); the two kinds of compounds having a polymerizable unsaturated group (C) are one kind of compound having an oxyalkylene group or a linear or branched alkyl group having 1 to 20 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) and one or two polymerizable unsaturated groups, and one kind of compound having a hydroxyl group and one or two polymerizable unsaturated groups.

[0138] In the above Mode A, the oxyalkylene group is preferably an oxyalkylene group represented by the above Formula 5. In this case, Y in the above Formula 5 1 is preferably a linear or branched alkylene group having 1 to 5 carbon atoms (1, 2, 3, 4, or 5), and m is preferably an integer of 2 to 15.

[0139] In the above Mode A, the linear or branched alkyl group preferably has 1 to 10 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, or 10).

[0140] In the above Mode A, the polymerizable unsaturated group is preferably at least one selected from the group consisting of an acryloyl group, a methacryloyl group, an acryloyloxy group, and a methacryloyloxy group, and more preferably an acryloyloxy group and / or a methacryloyloxy group.

[0141] In the above Mode A, the number of the hydroxyl groups is preferably one or two.

[0142] As another preferable mode (hereinafter, referred to as "Mode B") of the modified polyolefin resin composition, the following substances can be exemplified: The modified polyolefin resin composition contains an acid-modified polyolefin resin (A), a polyetheramine (B), a compound having a polymerizable unsaturated group (C), and an ionic liquid (D); the compound having a polymerizable unsaturated group (C) is at least one compound selected from the group consisting of neopentyl glycol diacrylate, 1,9-nonanediol diacrylate, tripropyleneglycol diacrylate, polypropyleneglycol diacrylate, 2-ethylhexyl acrylate, 4-hydroxybutyl acrylate, and 2-hydroxy-3-methacryloylpropyl acrylate.

[0143] <Polymerization initiator> As an embodiment, the modified polyolefin resin composition can also contain a polymerization initiator, as long as the effects of the present application are not impaired. By containing a polymerization initiator, the polymerization of the polymerizable unsaturated group of the compound (C) can further proceed favorably, and the resin for forming a coating film can be formed more easily. Furthermore, by using a polymerization initiator, the corrosion resistance and durability of the coating film are further improved.

[0144] From the viewpoint of improving the curing speed of the coating film obtained from the modified polyolefin resin composition, the amount of the polymerization initiator used is preferably 0.1 to 20 parts by mass, more preferably 1 to 10 parts by mass, and further preferably 2 to 5 parts by mass, relative to 100 parts by mass of the modified polyolefin resin composition.

[0145] As the polymerization initiator, a polymerization initiator capable of initiating the polymerization of the polymerizable unsaturated group can be used, and, for example, photopolymerization initiators that generate radicals by light, thermal polymerization initiators that generate radicals by heat, and the like can be listed. These polymerization initiators can be used individually or in combination of two or more.

[0146] The photopolymerization initiator is a compound that generates radicals or acid by irradiation of ultraviolet rays or visible light, and initiates chain polymerization. As the photopolymerization initiator, for example, acetophenone-based photopolymerization initiators, benzoin-based photopolymerization initiators, benzophenone-based photopolymerization initiators, thioxanthone-based photopolymerization initiators, acyloxyphosphine-based photopolymerization initiators, titanocene-based photopolymerization initiators, and the like can be listed. These photopolymerization initiators can be used individually or in combination of two or more.

[0147] As specific examples of the acetophenone-based photopolymerization initiator, diethoxyacetophenone, 2-hydroxy-2-methyl-l-phenyl-l-propanone, benzyl dimethyl ketal, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl) ketone, l-hydroxycyclohexyl phenyl ketone, 2-methyl-2-morpholino(4-thiomethylphenyl)-l-propanone, 2-benzyl-2-dimethylamino-l-(4-morpholinophenyl) butanone, 2-hydroxy-2-methyl-l-[4-(l-methylethenyl)phenyl]propanone oligomer, and the like can be listed. These can be used individually or in combination of two or more.

[0148] As specific examples of the benzoin-based photopolymerization initiator, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and the like can be listed. These can be used individually or in combination of two or more.

[0149] As specific examples of the benzophenone-based photopolymerization initiator, benzophenone, benzoylbenzoic acid, polyvinylbenzophenone, α-hydroxycyclohexyl phenyl ketone, and the like can be listed. These can be used individually or in combination of two or more.

[0150] As specific examples of the thioxanthone-based photopolymerization initiator, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4-diethylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, dodecylthioxanthone, and the like can be given. These can be used individually or in combination of two or more.

[0151] As specific examples of the acylphosphine oxide-based photopolymerization initiator, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, ethoxyphenyl(2,4,6-trimethylbenzoyl)phosphine oxide, and the like can be given. These can be used individually or in combination of two or more.

[0152] As specific examples of the titanocene-based photopolymerization initiator, bis(cyclopentadienyl)-bis[2,6-difluoro-3-(2-(1-pyrrol-1-yl)ethyl)phenyl]titanium, bis(cyclopentadienyl)-bis[2,6-difluoro-3-(3-(1-pyrrol-1-yl)propyl)phenyl]titanium, bis(cyclopentadienyl)-bis[2,6-difluoro-3-((1-pyrrol-1-yl)methyl)phenyl]titanium, bis(methylcyclopentadienyl)-bis[2,6-difluoro-3-((1-pyrrol-1-yl)methyl)phenyl]titanium, bis(cyclopentadienyl)-bis[2,6-difluoro-3-((2,5-dimethyl-1-pyrrol-1-yl)methyl)phenyl]titanium, bis(cyclopentadienyl)-bis[2,6-difluoro-3-((2-isopropyl-5-methyl-1-pyrrol-1,6-yl)methyl)phenyl]titanium, bis(cyclopentadienyl)-bis[2,6-difluoro-3-((2-(2-methoxyethyl)-5-methyl-1-pyrrol-1-yl)methyl)phenyl]titanium, and the like can be given. These can be used individually or in combination of two or more.

[0153] A thermal polymerization initiator is a compound that generates a radical by heating, and initiates a chain polymerization reaction. As the thermal polymerization initiator, for example, organic peroxides; inorganic peroxides such as potassium persulfate, ammonium persulfate, hydrogen peroxide, and the like can be given. As specific examples of the organic peroxides, ketone peroxide compounds such as methyl ethyl ketone peroxide, cyclohexanone peroxide, 3,3,5-trimethylcyclohexanone peroxide, methylcyclohexanone peroxide, methyl acetoacetate peroxide, acetylacetone peroxide, and the like can be given. 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(tert-butylperoxy)cyclohexane, 2,2-bis(tert-butylperoxy)octane, n-butyl 4,4-bis(tert-butylperoxy)valerate, 2,2-bis(tert-butylperoxy)butane, and the like can be given. tert-butyl hydroperoxide, cumyl hydroperoxide, di-cumyl hydroperoxide, p-menthane hydroperoxide, 2,5-dimethylhexane-2,5-dihydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, and the like; tert-butyl peroxide, tert-butyl cumyl peroxide, dicumyl peroxide, α,α'-bis(tert-butyl peroxyisopropyl)benzene, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane, 2,5-dimethyl-2,5-di(tert-butylperoxy)-3-hexyne, and the like dialkyl peroxide compounds; acetyl peroxide, isobutyryl peroxide, octanoyl peroxide, decanoyl peroxide, lauroyl peroxide, 3,5,5-trimethylhexanoyl peroxide, succinic acid peroxide, benzoyl peroxide, 2,4-dichlorobenzoyl peroxide, m-toluoyl peroxide, and the like diacyl peroxide compounds; diisopropyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, di-n-propyl peroxydicarbonate, bis(4-tert-butylcyclohexyl) peroxydicarbonate, dimyristyl peroxydicarbonate, di-2-ethoxyethyl peroxydicarbonate, dimethoxyisopropyl peroxydicarbonate, di(3-methyl-3-methoxybutyl) peroxydicarbonate, diallyl peroxydicarbonate, and the like peroxydicarbonate compounds; tert-butyl peroxyacetate, tert-butyl peroxyisobutyrate, tert-butyl peroxyneopentanoate, tert-butyl peroxyneodecanoate, cumyl peroxyneodecanoate, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxy-3,5,5-trimethylhexanoate, tert-butyl peroxylauroate, tert-butyl peroxybenzoate, di-tert-butyl peroxyisophthalate, 2,5-dimethyl-2,5-di(peroxybenzoyl)hexane, tert-butyl peroxymaleate, tert-butyl peroxyisopropylcarbonate, cumyl peroxyoctanoate, tert-hexyl peroxyneodecanoate, tert-hexyl peroxyneopentanoate, tert-butyl peroxyneohexanoate, tert-hexyl peroxyneohexanoate, cumyl peroxyneohexanoate, and the like peroxyester compounds; acetylcyclohexylsulfonyl peroxide, tert-butyl peroxyallylcarbonate, and the like. These organic peroxides can be used individually or in combination of two or more.

[0154] <UV absorber> As one embodiment, the modified polyolefin composition can further contain a UV absorber, as long as the effects of the present application are not impaired. As the UV absorber, for example, benzophenone-based UV absorbers, benzotriazole-based UV absorbers, triazine-based UV absorbers, salicylic acid-based UV absorbers, cyanoacrylate-based UV absorbers, benzoxazine-based UV absorbers, and the like can be exemplified. These UV absorbers can be used individually or in combination of two or more.

[0155] The amount of use of the ultraviolet absorber is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, relative to 100 parts by mass of the modified polyolefin resin composition.

[0156] <Light stabilizer> As one embodiment, the modified polyolefin composition can further contain a light stabilizer, as long as the effects of the present application are not impaired. As the light stabilizer, for example, a hindered amine-based light stabilizer can be exemplified.

[0157] As specific examples of the hindered amine-based light stabilizer, bis(l,2,2,6,6-pentamethyl-4-piperidyl) sebacate, methyl(l,2,2,6,6-pentamethyl-4-piperidyl) sebacate, 2,4-bis[n-butyl-N-(l-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)amino]-6-(2-hydroxyethoxy)amino-l,3,5-triazine, bis(2,2,6,6-tetramethyl-l-(octyloxy)-4-piperidyl) sebacate, and the like can be exemplified. These can be used individually or in combination of two or more.

[0158] The amount of use of the light stabilizer is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 1 part by mass, relative to 100 parts by mass of the modified polyolefin resin composition.

[0159] <Sensitizer> As an embodiment, the modified polyolefin composition can also contain a sensitizer, as long as the effect of the present application is not impaired. As the sensitizer, for example, mention can be made of unsaturated ketone compounds such as chalcone, dibenzalacetone, and the like, 1,2-diketone compounds such as benzil, camphor ketone, and the like, benzoin compounds, fluorene compounds, naphthoquinone compounds, anthraquinone compounds, xanthene compounds, thioxanthene compounds, xanthone compounds, thioxanthone compounds, coumarin compounds, coumarone compounds, cyanine compounds, merocyanine compounds, oxonol compounds, acridine compounds, azine compounds, thiazine compounds, oxazine compounds, indoline compounds, azulene compounds, azulenium compounds, squarylium compounds, porphyrin compounds, tetraphenylporphyrin compounds, triarylmethane compounds, tetraphenylporphyrin compounds, tetrapyrazinoporphyrazine compounds, phthalocyanine compounds, tetraazaporphyrazine compounds, tetraquinoxalyloporphyrazine compounds, naphthalocyanine compounds, subphthalocyanine compounds, pyrylium compounds, thiopyrylium compounds, tetraphyrin compounds, annulene compounds, spiropyran compounds, spirooxazine compounds, thiospiropyran compounds, metal arene complexes, organoruthenium complexes, Michler's ketone compounds, bisimidazole compounds, and the like. These can be used individually or in combination of two or more.

[0160] The amount of the sensitizer used is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, relative to 100 parts by mass of the modified polyolefin resin composition.

[0161] <Surfactant> As an embodiment, the modified polyolefin resin composition can also contain a surfactant, as long as the effect of the present application is not impaired. As the surfactant, for example, mention can be made of nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, and the like. These surfactants can be used individually or in combination of two or more. Among these, from the viewpoint of improving the stability of the modified polyolefin resin composition, it is preferred to use a nonionic surfactant or an anionic surfactant, more preferably a nonionic surfactant.

[0162] As the nonionic surfactant, for example, polyoxyethylene alkyl ether, polyoxypropylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxypropylene alkyl phenyl ether, polyoxyethylene styrenated phenyl ether, polyoxypropylene styrenated phenyl ether, polyoxyethylene fatty acid ester, polyoxypropylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxypropylene sorbitan fatty acid ester, polyoxyethylene alkyl amide, polyoxypropylene alkyl amide, polyoxyethylene lanolin alcohol ether, polyoxypropylene lanolin alcohol ether, polyoxyethylene lanolin fatty acid ester, polyoxypropylene lanolin fatty acid ester, (polyoxyethylene oxypropylene) block copolymer, and the like can be exemplified. These can be used individually or in combination of two or more. As the nonionic surfactant, widely known commercially available products can be used, for example, EMALUMIN series (manufactured by Sankyo Yuka Kogyo Co., Ltd.), NOIGEN series (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), BLAUNON series (manufactured by Aoki Oil & Fat Co., Ltd.), and the like can be exemplified.

[0163] As the anionic surfactant, for example, higher alkyl sulfate salt, alkyl aryl polyoxyethylene sulfate salt, higher fatty acid salt, alkyl aryl sulfonate salt, alkyl phosphate salt, and the like can be exemplified. These can be used individually or in combination of two or more. As the anionic surfactant, widely known commercially available products can be used, for example, NEOCOL series (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), HAITENOL series (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), and the like can be exemplified.

[0164] From the viewpoint of improving the stability of the modified polyolefin resin composition, the amount of the surfactant used is preferably 1 to 60 parts by mass, more preferably 3 to 40 parts by mass, and still more preferably 5 to 30 parts by mass, relative to 100 parts by mass of the acid-modified polyolefin resin (A).

[0165] <Various additives> As one embodiment, the modified polyolefin resin composition can further contain various additives as needed. As the various additives, for example, adhesion-imparting agents, film-forming aids, defoaming agents, anti-sagging agents, wetting agents, and the like can be exemplified.

[0166] As the adhesion-imparting agent, for example, rosin, dammar, polymerized rosin, hydrogenated rosin, ester rosin, rosin-modified maleic acid resin, polyterpene-based resin, petroleum-based resin, cyclopentadiene-based resin, phenol-based resin, xylene-based resin, coumarone-indene-based resin, and the like can be exemplified. These can be used individually or in combination of two or more.

[0167] The amount of the adhesion-imparting agent used is preferably 1 to 50 parts by mass, and more preferably 10 to 25 parts by mass, in 100 parts by mass of the modified polyolefin resin composition.

[0168] <Organic solvent> As one embodiment, the modified polyolefin resin composition can contain or not contain an organic solvent.

[0169] As one embodiment, when the modified polyolefin resin composition contains an organic solvent, it is preferable to contain a small amount of the organic solvent from the environmental and sanitary aspects. In this case, the content of the organic solvent is preferably 20 parts by mass or less, more preferably 10 parts by mass or less, still more preferably 5 parts by mass or less, further preferably 3 parts by mass or less, particularly preferably 1 part by mass or less, with respect to 100 parts by mass of the modified polyolefin resin composition. As one embodiment, when the modified polyolefin resin composition contains an organic solvent, the viscosity of the modified polyolefin resin composition is further reduced, and thus there is an advantage of further improving the coatability.

[0170] As one embodiment, when the modified polyolefin resin composition does not contain an organic solvent, the modified polyolefin resin composition can be preferably used as a main agent of a solvent-free radical curing type adhesive. In addition, as one embodiment, the solvent-free means that no organic solvent is intentionally added to the modified polyolefin resin composition, and the case where the organic solvent used for the production of the acid-modified polyolefin resin (A) remains is also included in the category of "solvent-free".

[0171] As the organic solvent, for example, aromatic hydrocarbons such as benzene, toluene, xylene and the like; aliphatic hydrocarbons such as hexane, heptane, octane, decane and the like; alicyclic hydrocarbons such as cyclohexane, cyclohexene, methylcyclohexane, ethylcyclohexane and the like; halogenated hydrocarbons such as trichloroethylene, dichloroethylene, chlorobenzene, chloroform and the like; alcohol-based solvents such as methanol, ethanol, isopropanol, butanol, pentanol, 1-hexanol, 2-ethylhexanol, 2-methylcyclohexanol, phenol, 2-heptanol and the like; ketone-based solvents such as acetone, methyl isobutyl ketone, methyl ethyl ketone, pentanone, hexanone, cyclohexanone, isophorone, phenylacetone and the like; cellusolve-based solvents such as methyl cellosolve, ethyl cellosolve and the like; ester-based solvents such as methyl acetate, ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, butyl formate and the like; ether-based solvents such as ethylene glycol mononormalbutyl ether, ethylene glycol monoisobutyl ether, ethylene glycol mono-tert-butyl ether, diethylene glycol mononormalbutyl ether, diethylene glycol mono-isobutyl ether, triethylene glycol mononormalbutyl ether, tetraethylene glycol mononormalbutyl ether, dibenzyl ether, diphenyl ether, butyl phenyl ether and the like can be exemplified. These can be used alone or in combination of two or more.

[0172] (Method for producing modified polyolefin resin composition) As the method for producing the modified polyolefin resin composition of the present application, a publicly known method can be widely used, and for example, the method described in the following steps (1) to (4) can be exemplified. Step (1): An acid-modified polyolefin resin (A) and a compound (C) having a polymerizable unsaturated group are charged into a stirrer equipped with a heating device, and mixed while being heated. Step (2): Further, polyether amine (B) is added to the kneader, and kneading is performed while heating. Step (3): Further, ionic liquid (D) is added to the kneader, and kneading is performed while heating. Step (4): Then, cooling to room temperature is performed, and the modified polyolefin resin composition is obtained by filtration.

[0173] In the above-mentioned step (1), the heating temperature at the time of kneading is usually 50 to 200°C, preferably 60 to 150°C, and more preferably 70 to 120°C. The kneading time is usually different depending on the heating temperature and the like, but is usually 10 minutes to 120 minutes, preferably 15 minutes to 90 minutes, and more preferably 20 minutes to 60 minutes.

[0174] In the above-mentioned step (2), the heating temperature at the time of kneading is usually 50 to 200°C, preferably 60 to 150°C, and more preferably 70 to 120°C. The kneading time is usually different depending on the heating temperature and the like, but is usually 10 minutes to 120 minutes, preferably 15 minutes to 90 minutes, and more preferably 20 minutes to 75 minutes.

[0175] In the above-mentioned step (3), the heating temperature at the time of kneading is usually 50 to 200°C, preferably 60 to 150°C, and more preferably 70 to 120°C. The kneading time is usually different depending on the heating temperature and the like, but is usually 10 minutes to 120 minutes, preferably 15 minutes to 90 minutes, and more preferably 20 minutes to 75 minutes.

[0176] In the above-mentioned step (4), filtration can be performed using, for example, a metal mesh having a mesh size of 50 to 300 μm.

[0177] (Cured product) The cured product of the present embodiment is a cured product of the modified polyolefin resin composition of the present embodiment. In other words, the cured product of the present embodiment is a substance after the modified polyolefin resin composition of the present embodiment is cured. Hereinafter, the above-mentioned cured product is simply denoted as "the cured product of the present embodiment".

[0178] (Use) The modified polyolefin resin composition of the present embodiment and the cured product of the present embodiment can be preferably used for a polyolefin base material. As the polyolefin base material, for example, a base material in which a polyolefin is processed into a block (a plate, a rod, a sphere, or the like), a sheet, a film, a wire, a cloth (woven cloth, knitted cloth, and non-woven cloth, or the like), or the like can be exemplified. Among these polyolefin base materials, from the viewpoint of manufacturing, a sheet and a film are preferable. As the thickness of the film, a film of 5 μm to 100 μm can be used. As the polyolefin, for example, polypropylene, polyethylene, an ethylene-propylene copolymer, an ethylene-propylene-diene copolymer, polybutylene, poly(4-methyl-l-pentene), or the like can be exemplified. The modified polyolefin resin composition of the present embodiment and the cured product of the present embodiment can be particularly preferably used for a polypropylene base material.

[0179] The modified polyolefin resin composition of the present embodiment and the cured product of the present embodiment can be preferably used for a coating for a molded body; an ink; an adhesive; a sealant; a primer; a coating agent, a coating for an in-mold paint, or the like. The modified polyolefin resin composition of the present embodiment and the cured product of the present embodiment can be particularly preferably used for an ink for a polyolefin base material, an adhesive for a polyolefin base material, a primer for a polyolefin base material, a coating for a polyolefin base material, and an in-mold paint coating for a polyolefin base material.

[0180] A coating film can be obtained from the modified polyolefin resin composition of the present embodiment. The coating film can be particularly preferably used for a metal product use, an electronic machine use, a packaging material use, an automobile part use, or the like.

[0181] As a method of forming a coating film from the modified polyolefin resin composition of the present embodiment, for example, a method in which the modified polyolefin resin composition of the present embodiment is uniformly applied to the surface of a variety of base materials, supplied to a heat treatment (for example, a sintering treatment, or the like), or the like can be exemplified. Thereby, a uniform coating film can be formed on the surface of a variety of base materials. As the method of application, for example, a gravure coating method, a curtain coating method, a Meyer bar coating method, a dip coating method, a brush coating method, a roll coating method, a spray coating method, or the like can be exemplified. The application amount of the modified polyolefin resin composition to the base material is not particularly limited, and is appropriately selected depending on the use thereof, and is preferably in the range of 1 μm to 100 μm of a dry coating film. The heat treatment can be performed using a hot air circulation type oven, an infrared heater, or the like. Further, a method in which, after a plastic base material is molded in a mold, the modified polyolefin resin composition of the present embodiment is injected between the mold and the base material, and a coating film is formed by applying heat and pressure can be exemplified. The heating temperature is usually 60 to 200°C. The heating time is usually 15 seconds to 20 minutes.

[0182] The present application provides the application of the following described mode. Item 1. A modified polyolefin resin composition containing an acid-modified polyolefin resin (A), a polyetheramine (B), a compound having a polymerizable unsaturated group (C), and an ionic liquid (D). Item 2. The modified polyolefin resin composition according to item 1, wherein the cation constituting the ionic liquid (D) is at least one cation selected from the group of tetraalkylammonium ion, imidazolium ion, pyridinium ion, pyrazolium ion, pyrrolium ion, pyrrolinium ion, pyrrolidinium ion, and piperidinium ion. Item 3. The modified polyolefin resin composition according to item 1 or 2, wherein the content of the ionic liquid (D) is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, further preferably 0.8 to 12.5 parts by mass, relative to 100 parts by mass of the modified polyolefin resin composition. Item 4. The modified polyolefin resin composition according to any one of items 1 to 3, wherein the cation of the ionic liquid (D) has a polymerizable unsaturated group. Item 5. The modified polyolefin resin composition according to any one of items 1 to 4, wherein the content of the acid-modified polyolefin resin (A) is preferably 5 to 120 parts by mass, more preferably 10 to 90 parts by mass, more preferably 12.5 to 70 parts by mass, more further preferably 15 to 50 parts by mass, further preferably 17.5 to 40 parts by mass, particularly preferably 20 to 35 parts by mass, relative to 100 parts by mass of the compound having a polymerizable unsaturated group (C). Item 6. The modified polyolefin resin composition according to any one of items 1 to 5, wherein the compound having a polymerizable unsaturated group (C) preferably contains a compound having a hydroxyl group and one or more polymerizable unsaturated groups, more preferably contains a compound having a hydroxyl group and one to four (1, 2, 3, or 4) polymerizable unsaturated groups, more further preferably contains a compound having a hydroxyl group and one or two polymerizable unsaturated groups. Item 7. The modified polyolefin resin composition according to any one of items 1 to 6, wherein the compound (C) having a polymerizable unsaturated group preferably contains a straight-chain or branched alkyl group having an oxyalkylene group and / or having 1 to 20 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20) and one or more polymerizable unsaturated groups, more preferably containing a compound having an oxyalkylene group and / or having 1 to 20 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20), and / or having one or more polymerizable unsaturated groups. Compounds comprising straight-chain or branched alkyl groups having 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms and 1 to 4 (1, 2, 3 or 4) polymerizable unsaturated groups, and more preferably compounds comprising straight-chain or branched alkyl groups having oxoalkylene and / or having 1 to 20 (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20) carbon atoms and 1 or 2 polymerizable unsaturated groups. Item 8. The modified polyolefin resin composition according to any one of items 1 to 7, wherein, relative to 100 parts by weight of the acid-modified polyolefin resin (A), the content of the polyetheramine (B) is generally 6 to 100 parts by weight, preferably 10 to 90 parts by weight, more preferably 15 to 80 parts by weight, even more preferably 20 to 70 parts by weight, even more preferably 25 to 60 parts by weight, and particularly preferably 30 to 50 parts by weight. Item 9. The modified polyolefin resin composition according to any one of items 1 to 8, wherein the polyetheramine (B) has a polyether chain, said polyether chain containing a component selected from... The structure represented by -(O-CH2CH2)x- (x is an integer from 2 to 120), The structure represented by -(O-CH2CH(CH3))y1- (y1 is an integer from 2 to 90) The structure represented by -(O-CH2CH2CH2)y2- (y2 is an integer from 2 to 90) The structure represented by -(O-CH2CH2CH2CH2)z1- (z1 is an integer from 2 to 80), The structure represented by -(O-CH(CH3)CH2CH2)z2- (z2 is an integer from 2 to 80), The structure represented by -(O-CH2CH(CH3)CH2)z3- (z3 is an integer from 2 to 80), and A structure of at least one of the groups of structures represented by -(O-CH2CH2CH(CH3))z4- (z4 is an integer from 2 to 80). Item 10. The modified polyolefin resin composition according to any one of items 1 to 9, wherein the polyether amine (B) preferably has a primary amino group or a secondary amino group at a single terminal end, and a weight average molecular weight (Mw) of 200 to 50,000; more preferably has a primary amino group or a secondary amino group at a single terminal end, and a Mw of 300 to 10,000; still more preferably has a primary amino group, and a Mw of 500 to 5,000. Item 11. The modified polyolefin resin composition according to any one of items 1 to 10, wherein the polyether amine (B) has an HLB value of preferably 2 to 20, more preferably 5 to 19, still more preferably 8 to 18. Item 12. The modified polyolefin resin composition according to any one of items 1 to 11, wherein the compound (C) having a polymerizable unsaturated group has a weight average molecular weight (Mw) of preferably 5,000 or less, more preferably 2,000 or less, still more preferably 1,000 or less. Item 13. The modified polyolefin resin composition according to any one of items 1 to 12, wherein the compound (C) having a polymerizable unsaturated group preferably contains a compound having a hydroxyl group and one or more polymerizable unsaturated groups, and a compound having an oxyalkylene group and / or a linear or branched alkyl group having 1 to 20 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) and one or more polymerizable unsaturated groups; more preferably contains a compound having a hydroxyl group and one to four (1, 2, 3, or 4) polymerizable unsaturated groups, and a compound having an oxyalkylene group and / or a linear or branched alkyl group having 1 to 20 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) and one to four (1, 2, 3, or 4) polymerizable unsaturated groups; still more preferably contains a compound having a hydroxyl group and one or two polymerizable unsaturated groups, and a compound having an oxyalkylene group and / or a linear or branched alkyl group having 1 to 20 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20) and one or two polymerizable unsaturated groups. Item 14. The modified polyolefin resin composition according to any one of items 1 to 13, wherein the acid-modified polyolefin resin (A) is a graft polymer having a structure in which a polyolefin resin is grafted with an α,β-unsaturated carboxylic acid or an acid anhydride thereof. Item 15. The modified polyolefin resin composition according to Item 14, wherein the polyolefin resin is preferably a copolymer selected from at least one of homopolymer polypropylene, propylene-α-olefin copolymer, homopolymer polyethylene, ethylene-α-olefin copolymer, poly(1-butene) and poly(1-butene-α-olefin copolymer), more preferably homopolymer polypropylene and / or propylene-α-olefin copolymer, and even more preferably homopolymer polypropylene or propylene-α-olefin copolymer. Item 16. The modified polyolefin resin composition according to any one of items 1 to 15, wherein the acid-modified polyolefin resin (A) is preferably 1 to 60% by mass, more preferably 4 to 50% by mass, even more preferably 7 to 40% by mass, even more preferably 10 to 35% by mass, and particularly preferably 15 to 30% by mass, relative to the total mass of the modified polyolefin resin composition. Item 17. The modified polyolefin resin composition according to any one of items 1 to 16, wherein the polyetheramine (B) has a polyether chain, the polyether chain being contained in... The structure represented by Equation 1: -(O-CH2CH2)x- (where x is an integer from 2 to 120) The structure of at least one of the following groups: -(O-CH2CH(CH3))y1- (where y1 is an integer from 2 to 90 in Equation 2-1) and -(O-CH2CH2CH2CH2)z1- (where z1 is an integer from 2 to 80 in Equation 3-1). Item 18. The modified polyolefin resin composition according to any one of items 1 to 17, wherein the polyetheramine (B) is a compound represented by the following formula 1A. R 1 -(OR 2 )aR 3 Formula 1A (In Equation 1A: R 1 and R 3 Each of the following can be independently represented as an amino group or a straight-chain or branched alkyl group having 1 to 10 (1, 2, 3, 4, 5, 6, 7, 8, 9 or 10) carbon atoms. R 2 A straight-chain or branched alkylene group having 2 to 4 (2, 3 or 4) carbon atoms. (where a is an integer from 1 to 120.) Item 19. The modified polyolefin resin composition according to Item 18, wherein, in Formula 1A, R 1 R represents a straight-chain or branched alkyl group with 1 to 10 carbon atoms (1, 2, 3, 4, 5, 6, 7, 8, 9, or 10). 2represents a linear or branched alkylene group having 2 to 4 (2, 3, or 4) carbon atoms, R 3 represents an amino group, and a is an integer of 1 to 120. Item 20. The modified polyolefin resin composition according to any one of Items 1 to 19, wherein the content ratio of the polyetheramine (B) is usually 0.5 to 40% by mass, preferably 1 to 30% by mass, more preferably 2 to 20% by mass, further more preferably 3 to 15% by mass, further preferably 4 to 12.5% by mass, particularly preferably 5 to 10% by mass, with respect to the total mass of the modified polyolefin resin composition. Item 21. The modified polyolefin resin composition according to any one of Items 1 to 20, wherein the weight average molecular weight (Mw) of the compound (C) having a polymerizable unsaturated group is preferably 100 or more and 5000 or less, more preferably 120 or more and 2000 or less, further more preferably 140 or more and 1000 or less. Item 22. The modified polyolefin resin composition according to any one of Items 1 to 21, wherein 1 or 2 kinds of the compound (C) having a polymerizable unsaturated group are contained. Item 23. The modified polyolefin resin composition according to any one of Items 6 to 22, wherein the number of the hydroxyl groups is preferably 1 or 2, more preferably 1. Item 24. The modified polyolefin resin composition according to any one of Items 1 to 23, wherein the content ratio of the compound (C) having a polymerizable unsaturated group is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, further more preferably 30 to 85% by mass, further preferably 40 to 80% by mass, with respect to the total mass of the modified polyolefin resin composition. Item 25. The modified polyolefin resin composition according to any one of Items 1 to 24, wherein the polymerizable unsaturated group in the compound (C) having a polymerizable unsaturated group is preferably at least one selected from the group of acryloyl group, methacryloyl group, acryloyloxy group, methacryloyloxy group, vinyl group, allyl group, propenyl group, isopropenyl group, maleimide group, and vinyl ether group, more preferably at least one selected from the group of acryloyl group, methacryloyl group, acryloyloxy group, and methacryloyloxy group, further more preferably acryloyloxy group and / or methacryloyloxy group. Item 26. The modified polyolefin resin composition according to any one of Items 1 to 25, wherein the ionic liquid (D) is composed of a cation and an anion. Item 27. The modified polyolefin resin composition according to any one of Items 1 to 26, wherein the anion is preferably a sulfonic acid anion, a carboxylic acid anion, a phosphoric acid anion, a sulfonamide anion, or a sulfonimide anion, more preferably a sulfonimide anion. Item 28. The modified polyolefin resin composition according to any one of items 4 to 27, wherein the polymerizable unsaturated group in the cation of the ionic liquid (D) is preferably at least one selected from the group of acryloyl group, methacryloyl group, acryloyloxy group and methacryloyloxy group, more preferably acryloyloxy group and / or methacryloyloxy group, and further more preferably acryloyloxy group. Item 29. The modified polyolefin resin composition according to any one of items 4 to 28, wherein the number of the polymerizable unsaturated group in the cation of the ionic liquid (D) is 1 or 2. Item 30. The modified polyolefin resin composition according to any one of items 1 to 29, wherein the total content ratio of the acid-modified polyolefin resin (A), the polyetheramine (B), the compound having a polymerizable unsaturated group (C) and the ionic liquid (D) is preferably more than 50 mass%, more than 55 mass%, more than 60 mass%, more than 65 mass%, more than 70 mass%, more than 75 mass%, more than 80 mass%, more than 85 mass%, more than 90 mass%, more than 92.5 mass%, more than 95 mass%, more than 97.5 mass%, more than 99 mass%, more than 99.5 mass%, more than 99.9 mass%, more than 99.95 mass% and more than 99.99 mass% in the order, with respect to the total mass of the modified polyolefin resin composition. Item 31. A cured product of the modified polyolefin resin composition according to any one of items 1 to 30. Item 32. An ink containing the modified polyolefin resin composition according to any one of items 1 to 30 or the cured product according to item 31. Item 33. An adhesive containing the modified polyolefin resin composition according to any one of items 1 to 30 or the cured product according to item 31. Item 34. A primer containing the modified polyolefin resin composition according to any one of items 1 to 30 or the cured product according to item 31. Item 35. A paint containing the modified polyolefin resin composition according to any one of items 1 to 30 or the cured product according to item 31. Item 36. An in-mold paint containing the modified polyolefin resin composition according to any one of items 1 to 30 or the cured product according to item 31. EXAMPLES

[0183] Then, the present application will be specifically described based on Examples, but the present application is not limited to the following Examples. Hereinafter, "room temperature" means a temperature in the range of 20°C to 25°C.

[0184] (1) Measurement of Weight Average Molecular Weight (Mw) Based on High Temperature GPC GPC150-C PLUS manufactured by Waters Corporation was used, and the measurement was performed at 140°C using o-dichlorobenzene as a solvent. (Column: "GMH6-HT" + "GMH6-HTL" manufactured by Tosoh Corporation). The weight average molecular weight (Mw) was calculated using polystyrene having a known molecular weight as a standard substance.

[0185] (2) Measurement of melting point based on differential scanning calorimeter (DSC) According to JIS K7121-2012, using a DSC measuring device (manufactured by Junko Electronics Industry), about 5 mg of a sample was kept in a heated molten state at 150°C for 10 minutes, and then temperature was decreased at a rate of 10°C / minute, and kept stably at -50°C. Further, the melting peak temperature at the time of melting by increasing the temperature at a rate of 10°C / minute to 150°C was measured, and the melting point was evaluated based on the melting peak temperature.

[0186] (Production Example 1) Into an autoclave equipped with a stirrer, 280 g of a propylene-α-olefin copolymer (content of propylene component = 70 mol%), 62 g of maleic anhydride, 7 g of dicumyl peroxide, and 420 g of toluene were added, and after nitrogen substitution for about 5 minutes, reaction was performed at 140°C for 5 hours while heating and stirring. After the completion of the reaction, the reaction liquid was poured into a large amount of methyl ethyl ketone to precipitate the resin. Further, the resin was washed several times with methyl ethyl ketone to remove unreacted maleic anhydride. By drying the obtained resin under reduced pressure, a solid of an acid-modified polyolefin resin (MPO-1) was obtained. According to the measurement results of infrared absorption spectrum, the total content of the maleic anhydride component and the maleic acid component in MPO-1 was 2.0 mass%, and the acid value of the maleic anhydride component and the maleic acid component was 22.4 mgKOH / g. In addition, the weight average molecular weight (Mw) based on the high temperature GPC measurement of MPO-1 was 70000, and the melting point based on DSC was 70°C.

[0187] (Production Example 2) Into an autoclave equipped with a stirrer, 280 g of a propylene homopolymer (homopolypropylene, content of propylene component = 100 mol%), 36 g of maleic anhydride, 5.6 g of dicumyl peroxide and 420 g of toluene were charged, and after nitrogen substitution for about 5 minutes, reaction was performed at 140°C for 5 hours with heating and stirring. After completion of the reaction, the reaction liquid was poured into a large amount of methyl ethyl ketone to precipitate the resin. The resin was further washed several times with methyl ethyl ketone to remove unreacted maleic anhydride. By drying the obtained resin under reduced pressure, a solid of an acid-modified polyolefin resin (MPO-2) was obtained. From the results of measurement of infrared absorption spectrum, the total content of the maleic anhydride component and the maleic acid component in MPO-2 was 1.8 mass%, and the acid value of the maleic anhydride component and the maleic acid component was 20.2 mgKOH / g. Further, the weight average molecular weight (Mw) determined based on high temperature GPC of MPO-2 was 40000, and the melting point based on DSC was 75°C.

[0188] (Production Example 3) Into an autoclave equipped with a stirrer, 280 g of a propylene homopolymer (homopolypropylene, content of propylene component = 100 mol%), 36 g of maleic anhydride, 5.6 g of dicumyl peroxide and 420 g of toluene were charged, and after nitrogen substitution for about 5 minutes, reaction was performed at 140°C for 5 hours with heating and stirring. After completion of the reaction, the reaction liquid was poured into a large amount of methyl ethyl ketone to precipitate the resin. The resin was further washed several times with methyl ethyl ketone to remove unreacted maleic anhydride. By drying the obtained resin under reduced pressure, a solid of an acid-modified polyolefin resin (MPO-2) was obtained. From the results of measurement of infrared absorption spectrum, the total content of the maleic anhydride component and the maleic acid component in MPO-2 was 1.8 mass%, and the acid value of the maleic anhydride component and the maleic acid component was 20.2 mgKOH / g. Further, the weight average molecular weight (Mw) determined based on high temperature GPC of MPO-2 was 40000, and the melting point based on DSC was 75°C.

[0189] (Use materials) The materials used in the examples and comparative examples are described below. <Acid-modified polyolefin resin (A)> • MPO-1 (total content of maleic anhydride component and maleic acid component = 2.0 mass%, Mw determined based on high temperature GPC = 70000, melting point based on DSC = 70°C) obtained in Production Example 1 • MPO-2 obtained in Production Example 2 (total content of maleic anhydride component and maleic acid component = 1.8 mass%, Mw determined based on high temperature GPC = 40,000, melting point based on DSC = 75°C) • CPO-1 obtained in Production Example 3 (chlorine content = 21 mass%, content of maleic anhydride component = 1.0 mass%, Mw determined based on high temperature GPC = 80,000, melting point based on DSC = 75°C) < Polyether amine (B) > • "JEFFAMINE M-2070 (Mw = 2,000, HLB value = 13.8)" manufactured by HUNTSMAN Co. (number of primary amino groups = 1, number of secondary amino groups = 0) • "JEFFAMINE M-1000 (Mw = 1,000, HLB value = 16.1)" manufactured by HUNTSMAN Co. (number of primary amino groups = 1, number of secondary amino groups = 0) • "JEFFAMINE M-2005 (Mw = 2,000, HLB value = 2.7)" manufactured by HUNTSMAN Co. (number of primary amino groups = 1, number of secondary amino groups = 0) < Compound (C) having a polymerizable unsaturated group > [Compound having an oxyalkylene group and 2 polymerizable unsaturated groups] • Neopentyl glycol diacrylate (Mw = 212) (manufactured by Tokyo Chemical Industry Co., Ltd.) • 1,9-nonanediol diacrylate (Mw = 268) (manufactured by Tokyo Chemical Industry Co., Ltd.) • Tripropylene glycol diacrylate (Mw = 300) (manufactured by Tokyo Chemical Industry Co., Ltd.) • Polypropylene glycol diacrylate (polypropylene glycol #700 diacrylate, number of repeating units = 12, Mw = 808, manufactured by Shin Nakamura Chemical Co., Ltd., NK ESTER (registered trademark) "APG-700") [Compound having a branched alkyl group having 8 carbon atoms and 1 polymerizable unsaturated group] • Acrylic acid-2-ethylhexyl ester (Mw = 184) (manufactured by Tokyo Chemical Industry Co., Ltd.) [Compound having a hydroxyl group and 1 polymerizable unsaturated group] • Acrylic acid-4-hydroxybutyl ester (Mw = 144) (manufactured by Tokyo Chemical Industry Co., Ltd.) [Compound having a hydroxyl group and 2 polymerizable unsaturated groups] • 2-Hydroxy-3-methacryloylpropyl acrylate (Mw = 214) (manufactured by Tokyo Chemical Industry Co., Ltd.) < Ionic liquid (D) > • (2-acryloyloxyethyl) trimethylammonium-bis(trifluoromethylsulfonyl) imide (manufactured by Goin Chemical Industry Co., Ltd.) • Methyltrioctylammonium-bis(trifluoromethylsulfonyl) imide (manufactured by Goin Chemical Industry Co., Ltd.)

[0190] (Example 1) To a 200-mL 4-necked flask equipped with a cooler, a thermometer, and a stirrer, 20 g of MPO-1 as an acid-modified polyolefin resin (A), 50 g of neopentyl glycol diacrylate as a compound having a polymerizable unsaturated group (C), and 30 g of 2-hydroxy-3-methacryloylpropyl acrylate were added, and the internal temperature was warmed to 90°C, and heating dissolution was performed for 30 minutes. Then, 8 g of "JEFFAMINE M-2070" as a polyether amine (B) was added, and stirring was performed at 90°C for 1 hour. Further, 1.0 g of (2-acryloyloxyethyl) trimethylammonium-bis(trifluoromethylsulfonyl) imide as an ionic liquid (D) was added, and stirring was performed at 90°C for 1 hour. Then, cooling was performed to room temperature, and filtration was performed using a metal mesh having a mesh size of 149 μm, to obtain a modified polyolefin resin composition (a).

[0191] (Examples 2 to 18) A modified polyolefin resin composition (b) to (r) was obtained by the same method as in Example 1, except that the kinds and the amounts of use of the acid-modified polyolefin resin (A), the polyether amine (B), the compound having a polymerizable unsaturated group (C), and the ionic liquid (D) were changed to those shown in Tables 1 and 2.

[0192] (Comparative Example 1) To a 200-mL 4-necked flask equipped with a cooler, a thermometer, and a stirrer, 20 g of MPO-1 as an acid-modified polyolefin resin (A), 50 g of neopentyl glycol diacrylate as a compound having a polymerizable unsaturated group (C), and 30 g of 2-hydroxy-3-methacryloylpropyl acrylate were added, and the internal temperature was warmed to 90°C, and heating dissolution was performed for 30 minutes. Then, 8 g of "JEFFAMINE M-2070" as a polyether amine (B) was added, and stirring was performed at 90°C for 1 hour. Then, cooling was performed to room temperature, and filtration was performed using a metal mesh having a mesh size of 149 μm, to obtain a modified polyolefin resin composition (s). Further, in Comparative Example 1, the ionic liquid (D) was not used.

[0193] (Comparative Example 2) To a 200-milliliter 4-port flask equipped with a cooler, a thermometer, and a stirrer, 50 g of neopentyl glycol diacrylate as the compound (C) having a polymerizable unsaturated group and 30 g of 2-hydroxy-3-methyl acryloyl propyl acrylate were added, and the inside temperature was warmed to 90°C, and heating dissolution was performed for 30 minutes. Then, 8 g of "JEFFAMINE M-2070" as the polyether amine (B) was added, and stirring was performed at 90°C for 1 hour. Then, 1.0 g of (2-acryloyloxyethyl) trimethylammonium-bis(trifluoromethylsulfonyl) imide as the ionic liquid (D) was added, and stirring was performed at 90°C for 1 hour. Then, cooling was performed to room temperature, and a resin composition (t) was obtained by filtration using a metal mesh having a mesh size of 149 μm. Further, in Comparative Example 2, the acid-modified polyolefin resin (A) was not used.

[0194] (Comparative Example 3) To a 200-milliliter 4-port flask equipped with a cooler, a thermometer, and a stirrer, 20 g of MPO-1 as the acid-modified polyolefin resin (A), 50 g of neopentyl glycol diacrylate as the compound (C) having a polymerizable unsaturated group, and 30 g of 2-hydroxy-3-methyl acryloyl propyl acrylate were added, and the inside temperature was warmed to 90°C, and heating dissolution was performed for 30 minutes. Then, 1.0 g of (2-acryloyloxyethyl) trimethylammonium-bis(trifluoromethylsulfonyl) imide as the ionic liquid (D) was added, and stirring was performed at 90°C for 1 hour. Then, cooling was performed to room temperature, but the resin was precipitated, and a modified polyolefin resin composition could not be obtained. Further, in Comparative Example 3, the polyether amine (B) was not used.

[0195] (Comparative Example 4) To a 200-milliliter 4-port flask equipped with a cooler, a thermometer, and a stirrer, 80 g of 1-propanol was added, and the inside temperature was warmed to 90°C, and heating dissolution was performed for 30 minutes. Then, 8 g of "JEFFAMINE M-2070" as the polyether amine (B) was added, and stirring was performed at 90°C for 1 hour. Then, 1.0 g of (2-acryloyloxyethyl) trimethylammonium-bis(trifluoromethylsulfonyl) imide as the ionic liquid (D) was added, and stirring was performed at 90°C for 1 hour. Then, cooling was performed to room temperature, and a resin composition (u) was obtained by filtration using a metal mesh having a mesh size of 149 μm. Further, in Comparative Example 4, the compound (C) having a polymerizable unsaturated group was not used.

[0196] (1) Evaluation of flowability at 25°C and 80°C For the modified polyolefin resin composition obtained in the examples and the resin composition obtained in the comparative example, the flowability at 25°C and 80°C immediately after production, the flowability at 25°C and 80°C the day after (24 hours after production), the flowability at 25°C and 80°C after 1 week (168 hours after production), and the flowability at 25°C and 80°C after 2 weeks (336 hours after production) were evaluated by visual observation. The case where flowability was observed after 2 weeks was evaluated as, the case where flowability was observed after 1 week was evaluated as, the case where flowability was observed the day after was evaluated as, the case where flowability was observed only immediately after production was evaluated as, and the case where flowability was not observed at all after production was evaluated as.

[0197] (2) Evaluation of Adhesion The adhesion of the modified polyolefin resin composition obtained in the examples to polypropylene (PP) bumper substrates, ABS substrates, and PET substrates, and the adhesion of the resin composition obtained in the comparative example to PP bumper substrates, ABS substrates, and PET substrates were evaluated. Specifically, 0.15 g of t-butyl peroxy-2-ethylhexanoate was added to 5 g of the modified polyolefin resin composition obtained in the examples and 5 g of the resin composition obtained in the comparative example, and the mixture was stirred at room temperature for 30 minutes using a magnetic stirrer. The mixture was coated onto PP (polypropylene) bumper substrates washed with isopropyl alcohol, ABS substrates washed with isopropyl alcohol, and PET substrates washed with isopropyl alcohol at a dry film thickness of about 10 μm using a bar coater No. 16 at room temperature. After sintering at 110°C for 10 minutes, the test panels were left to stand in an atmosphere of 25°C and 60% relative humidity for 72 hours. On each test panel, 100 squares reaching the substrate were made at intervals of 1 mm, and a transparent tape was attached thereto, and the tape was repeatedly peeled off at an angle of 90 degrees to the coated surface three times. The case where peeling did not occur even after the tape was peeled off three times was evaluated as, the case where peeling occurred at the third peeling was evaluated as, and the case where peeling occurred at the first or second peeling was evaluated as.

[0198] (3) Evaluation of Initial Antistatic Property The mixture prepared by the same method as in (2) was coated onto a PET film (Toyo Rika Co., Ltd., A4360) at a dry film thickness of 10 μm using a bar coater No. 5 at room temperature. Then, the surface resistance value (Ω / sq.) of the coated film was measured according to JIS K-6271-2008 (double ring electrode method) in an atmosphere of 25°C and 50% relative humidity after leaving to stand for 12 hours in the same atmosphere. The case where the surface resistance value was less than 10 11 Ω / sq. was evaluated as, the case where the surface resistance value was 10 11 Ω / sq. or more and less than 10 13 Ω / sq. was evaluated as, and the case where the surface resistance value was 1013 The case where the surface resistance value is less than 10

[0199] (4) Long-term antistatic property The mixture prepared by the same method as (2) was applied to a PET film (Toyo Rika Co., Ltd., A4360) using a bar coater No. 5 at a dry film thickness of 10 μm at room temperature. Then, after being left to stand for 1000 hours in an atmosphere of 25°C and 50% relative humidity, the surface resistance value (Ω / sq.) of the applied film was measured according to JIS K-6271-2008 (double ring electrode method) in the same atmosphere. The case where the surface resistance value was less than 10 11 The case where the surface resistance value was less than 10 11 The case where the surface resistance value was less than 10 13 The case where the surface resistance value was less than 10 13 The case where the surface resistance value was less than 10

[0200] The raw materials used and the amounts thereof, the evaluation results of the modified polyolefin resin compositions (a) to (r) obtained in Examples 1 to 18, the evaluation results of the resin compositions (s) to (u) obtained in Comparative Examples 1, 2, and 4, and the like are shown in Table 1 and Table 2 below. Further, with respect to Comparative Example 3, since the resin composition was not obtained, the adhesion to each substrate, the initial antistatic property, and the long-term antistatic property were all noted as "not evaluated".

[0201] [Table 1]

[0202] [Table 2]

[0203] [Investigation of the results of Table 1 and Table 2] The modified polyolefin resin compositions (a) to (r) obtained in Examples 1 to 18 showed flowability at both 25°C and 80°C after manufacture. In addition, the modified polyolefin resin compositions (a) to (r) obtained in Examples 1 to 18 showed good adhesion to PP bumper substrates, ABS substrates, and PET substrates. On the other hand, in the resin composition (s) obtained in Comparative Example 1, since the ionic liquid (D) was not used, a result showing a significant deterioration in initial antistatic properties and long-term antistatic properties was shown. In the resin composition (t) obtained in Comparative Example 2, since the modified polyolefin resin (A) was not used, a result showing a significant deterioration in PP adhesion was shown. In Comparative Example 3, since the polyetheramine (B) was not used, the resin was precipitated and the resin composition itself could not be manufactured. In Comparative Example 4, since the compound (C) having a polymerizable unsaturated group was not used, a result showing a significant deterioration in adhesion to ABS substrates and PET substrates was shown.

Claims

1. A modified polyolefin resin composition comprising an acid-modified polyolefin resin (A), a polyether amine (B), a compound having a polymerizable unsaturated group (C), and an ionic liquid (D).

2. The modified polyolefin resin composition according to claim 1, wherein, The cation constituting the ionic liquid (D) is at least one selected from the group of tetraalkylammonium cations, imidazolium cations, pyridinium cations, pyrazolium cations, pyrrolium cations, pyrrolinium cations, pyrrolidinium cations, and piperidinium cations.

3. The modified polyolefin resin composition according to claim 1, wherein, The content of the ionic liquid (D) is 0.1 to 20 parts by mass with respect to 100 parts by mass of the modified polyolefin resin composition.

4. The modified polyolefin resin composition according to claim 1, wherein, The cation of the ionic liquid (D) has a polymerizable unsaturated group.

5. The modified polyolefin resin composition according to claim 1, wherein, The content of the acid-modified polyolefin resin (A) is 5 to 120 parts by mass with respect to 100 parts by mass of the compound having a polymerizable unsaturated group (C).

6. The modified polyolefin resin composition according to claim 1, wherein, The compound having a polymerizable unsaturated group (C) contains a compound having a hydroxyl group and one or more polymerizable unsaturated groups.

7. The modified polyolefin resin composition according to claim 1, wherein, The compound having a polymerizable unsaturated group (C) contains a compound having an oxyalkylene group and / or a linear or branched alkyl group having 1 to 20 carbon atoms, and one or more polymerizable unsaturated groups.

8. The modified polyolefin resin composition according to claim 1, wherein, The content of the polyether amine (B) is 6 to 100 parts by mass with respect to 100 parts by mass of the acid-modified polyolefin resin (A).

9. The modified polyolefin resin composition according to claim 1, wherein, The polyether amine (B) has a polyether chain, which is at least one selected from the group of structures represented by -(0-CH2CH2)x-, a structure represented by -(0-CH2CH(CH3))y1-, a structure represented by -(0-CH2CH2CH2)y2-, a structure represented by -(0-CH2CH2CH2CH2)z1-, a structure represented by -(0-CH(CH3)CH2CH2)z2-, a structure represented by -(0-CH2CH(CH3)CH2)z3-, a structure represented by -(0-CH2CH2CH(CH3))z4-, and the x is an integer of 2 to 120, the y1 and y2 are integers of 2 to 90, and the z1, z2, z3, and z4 are integers of 2 to 80. The polyether amine (B) has a primary or secondary amino group at a single terminal end; and the weight average molecular weight Mw of the polyether amine (B) is 200 to 50,000.

10. The modified polyolefin resin composition according to claim 1, wherein, The HLB value of the polyether amine (B) is 2 to 20.

11. The modified polyolefin resin composition according to claim 1, wherein, The weight average molecular weight Mw of the compound having a polymerizable unsaturated group (C) is 5,000 or less.

12. The modified polyolefin resin composition according to claim 1, wherein, The compound having a polymerizable unsaturated group (C) contains:

13. The modified polyolefin resin composition according to claim 1, wherein, a compound having a hydroxyl group and one or more polymerizable unsaturated groups, and a compound having an oxyalkylene group and / or a linear or branched alkyl group having 1 to 20 carbon atoms, and one or more polymerizable unsaturated groups.

14. A cured product cured from the modified polyolefin resin composition according to any one of claims 1 to 13.

15. An ink containing the modified polyolefin resin composition according to any one of claims 1 to 13.

16. An adhesive containing the modified polyolefin resin composition according to any one of claims 1 to 13. ​ 17. A primer comprising the modified polyolefin resin composition according to any one of claims 1 to 13.

18. A coating comprising the modified polyolefin resin composition according to any one of claims 1 to 13.

19. An in-mold paint coating comprising the modified polyolefin resin composition according to any one of claims 1 to 13.

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