Polar-group-containing olefin copolymer, polar-group-containing multinary olefin copolymer, olefin-based resin composition, and adhesive and layered product each using the same

Patent metadata

Field	Value
Publication number	US-11084957-B2
Application number	US-201816200090-A
Country	US
Kind code	B2
Filing date	Nov 26, 2018
Priority date	Mar 27, 2013
Publication date	Aug 10, 2021
Grant date	Aug 10, 2021

Abstract

A method of producing a polar-group-containing olefin copolymer which comprises 99.999 to 80 mol % of structural units derived from at least one of ethylene and α-olefin having 3 to 20 carbon atoms and 20 to 0.001 mol % of structural units derived from at least one polar-group-containing monomer which contains an epoxy group and is represented by structural formula (I) or (II), the method comprising random copolymerization in the presence of a transition metal catalyst to obtain a copolymer having a linear molecular structure.

First claim

What is claimed is:

1. A method of producing a polar-group-containing olefin copolymer which comprises 99.999 to 80 mol % of structural units derived from at least one of ethylene or α-olefin having 3 to 20 carbon atoms and 20 to 0.001 mol % of structural units derived from at least one polar-group-containing monomer which contains an epoxy group and is represented by the following structural formula (I), the method comprising copolymerizing at least one of ethylene or α-olefin having 3 to 20 carbon atoms and at least one polar-group-containing monomer which contains an epoxy group and is represented by structural formula (I) in the presence of a transition metal catalyst comprising a chelatable ligand and a Group-5 to Group-11 metal to produce a random copolymer having a linear molecular structure,
wherein structural formula (I) is:

in which R 1 represents a hydrogen atom and R 2 , R 3 , and R 4 each independently represents a hydrogen atom, a hydrocarbon group, or an epoxy-group-containing functional group, wherein at least one of R 2 to R 4 comprises the epoxy-group-containing functional group,
wherein the polar-group-containing olefin copolymer has a melting point of 50 to 140° C., the melting point is determined by a differential scanning calorimeter by heating the copolymer to 200° C. at 10° C./minute, maintaining a temperature of 200° C. for 5 minutes, cooling the copolymer to 30° C. at 10° C./minute, maintaining a temperature at 30° C. for 5 minutes, and then heating the copolymer at 10° C./minute to obtain an endothermic curve for this heating, a maximum-peak temperature in the endothermic curve is the melting point; and
wherein an amount of aluminum (Al) in the polar-group-containing olefin copolymer, as measured by X-ray fluorescence analysis, is 0 to 171 μg per g of the copolymer.

2. The method according to claim 1 , wherein the polar-group-containing olefin copolymer has a weight-average molecular weight (Mw), as determined by gel permeation chromatography (GPC), of 1,000 to 2,000,000.

3. The method according to claim 1 , wherein the transition metal catalyst comprises palladium or nickel and a triarylphosphine or triarylarsine compound coordinated thereto.

4. The method according to claim 1 , further comprising forming an adhesive which comprises the polar-group-containing olefin copolymer.

5. The method according to claim 1 , further comprising forming a layered product which comprises the polar-group-containing olefin copolymer and a base layer.

6. The method according to claim 5 , wherein the base layer comprises at least one member selected from olefin-based resins, highly polar thermoplastic resins, metals, vapor-deposited films of inorganic oxide, paper, cellophane, woven fabric, or nonwoven fabric.

7. The method according to claim 5 , wherein the base layer comprises at least one member selected from polyamide-based resins, fluororesins, polyester-based resins, or ethylene/vinyl alcohol copolymers (EVOH).

8. A method of producing an olefin-based resin composition comprising a polar-group-containing olefin copolymer (A′) and an olefin-based resin (C), the method comprising producing a polar-group-containing olefin copolymer which comprises 99.999 to 80 mol % of structural units derived from at least one of ethylene or α-olefin having 3 to 20 carbon atoms and 20 to 0.001 mol % of structural units derived from at least one polar-group-containing monomer which contains an epoxy group and is represented by the following structural formula (I), by copolymerizing at least one of ethylene or α-olefin having 3 to 20 carbon atoms and at least one polar-group-containing monomer which contains an epoxy group and is represented by structural formula (I) in the presence of a transition metal catalyst comprising a chelatable ligand and a Group-5 to Group-11 metal to produce a random copolymer having a linear molecular structure,
wherein structural formula (I) is:

in which R 1 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R 2 , R 3 , and R 4 each independently represents a hydrogen atom, a hydrocarbon group, or an epoxy-group-containing functional group, wherein at least one of R 2 to R 4 comprises the epoxy-group-containing functional group,
wherein the polar-group-containing olefin copolymer has a melting point of 50 to 140° C., the melting point is determined by a differential scanning calorimeter by heating the copolymer to 200° C. at 10° C./minute, maintaining a temperature of 200° C. for 5 minutes, cooling the copolymer to 30° C. at 10° C./minute, maintaining a temperature at 30° C. for 5 minutes, and then heating the copolymer at 10° C./minute to obtain an endothermic curve for this heating, a maximum-peak temperature in the endothermic curve is the melting point; and
wherein an amount of aluminum (Al) in the polar-group-containing olefin copolymer is 0 to 10,000 μg per g of the copolymer; and combining the polar-group-containing olefin copolymer (A′) and an olefin-based resin (C).

9. The method of producing the olefin-based resin composition according to claim 8 , wherein the olefin-based resin (C) is at least one of a homopolymer or a copolymer, and the homopolymer or the copolymer is obtained by polymerizing a monomer selected from at least one of ethylene or α-olefin having 3 to 20 carbon atoms.

10. The method of producing the olefin-based resin composition according to claim 8 , wherein the olefin-based resin (C) is either an ethylene homopolymer or a copolymer of ethylene with α-olefin having 3 to 20 carbon atoms.

11. The method of producing the olefin-based resin composition according to claim 8 , wherein the polar-group-containing olefin copolymer (A′) is a copolymer obtained by polymerization in the presence of a transition metal catalyst which comprises palladium or nickel and a triarylphosphine or triarylarsine compound coordinated thereto.

12. The method of producing the olefin-based producing composition according to claim 8 , wherein the olefin-based resin (C) has a density, as measured in accordance with JIS K7112, of 0.890 to 1.20 g/cm 3 .

13. The method of producing the olefin-based resin composition according to claim 8 , wherein the olefin-based resin (C) has a melting point of 90 to 170° C., and the melting point is a temperature corresponding to a maximum peak in an endothermic curve determined by differential scanning calorimetry (DSC).

14. The method of producing the olefin-based resin composition according to claim 8 , wherein a melting point of olefin-based resin (C), which is a temperature corresponding to a maximum peak in an endothermic curve determined by differential scanning calorimetry (DSC), is 119 to 170° C.

15. The method of producing the olefin-based resin composition according to claim 8 , which has a heat of fusion ΔH, as determined by differential scanning calorimetry (DSC), of 80 to 300 J/g.

16. The method of producing the olefin-based resin composition according to claim 8 , wherein the olefin-based resin (C) has a melting point of 30 to 124° C., and the melting point is a temperature corresponding to a maximum peak in an endothermic curve determined by differential scanning calorimetry (DSC).

17. The method according to claim 8 , further comprising forming an adhesive which comprises the olefin-based resin composition.

18. Th

Assignees

• Japan Polyethylene Corp
• Japan Polypropylene Corp

Inventors

• Uematsu Masahiro
• Abe Kazunari
• Shimizu Hiroyuki
• Morioka Tetsuya

Classifications

• B32B27/32 Primary

  comprising polyolefins {(comprising vinyl (co)polymers or acrylic (co)polymers B32B27/30)} · CPC title

• B32B23/08

  of synthetic resin · CPC title

• B32B5/022

  Non-woven fabric · CPC title

• B32B5/024

  Woven fabric · CPC title

• C09J123/00

  Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers · CPC title