# US 11,999,842 B2 · Thermoplastic resin composition comprising a fluororesin and a crosslinked fluoroelastomer and method for producing the same

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- Number: US 11,999,842 B2
- Document ID: US11999842B2
- Status: Granted
- Kind: B2
- Application number: 16/975,972
- Filed: 2019-02-26
- Published: 2021-02-11
- Granted: 2024-06-04
- Earliest claimed: 2018-02-28
- Assignees: Daikin Industries, Ltd.
- Applicants: Daikin Industries, Ltd.
- Inventors: Akinori Ueda; Tsuyoshi Ono; Katsusada Tokuhira
- Web page: https://patentgrep.com/patent/US11999842B2

## CPC

- C08L 27/16: Homopolymers or copolymers or vinylidene fluoride
- B32B 1/08: Tubular products
- B32B 25/08: of synthetic resin
- B32B 25/14: comprising {synthetic rubber copolymers (B32B25/18 and B32B25/20 take precedence)}
- B32B 25/16: comprising polydienes {homopolymers} or poly-halodienes {homopolymers (B32B25/12 takes precedence)}
- B32B 25/18: comprising butyl or halobutyl rubber
- B32B 25/20: comprising silicone rubber
- B32B 27/20: using fillers, pigments, thixotroping agents
- B32B 27/304: {comprising vinyl halide (co)polymers, e.g. PVC, PVDC, PVF, PVDF}
- B32B 27/32: comprising polyolefins {(comprising vinyl (co)polymers or acrylic (co)polymers B32B27/30)}
- B32B 27/322: {comprising halogenated polyolefins, e.g. PTFE}
- B32B 27/34: comprising polyamides
- B32B 27/36: comprising polyesters
- B32B 27/40: comprising polyurethanes
- C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K)
- C08K 3/22: of metals
- C08K 5/18: with aromatically bound amino groups
- C08K 5/3465: condensed with carbocyclic rings
- C08K 5/50: Phosphorus bound to carbon only
- C08L 27/06: Homopolymers or copolymers of vinyl chloride
- C08L 27/18: Homopolymers or copolymers or tetrafluoroethene
- C08L 27/20: Homopolymers or copolymers of hexafluoropropene
- C08L 27/22: modified by chemical after-treatment
- B32B 2250/02: 2 layers
- B32B 2250/24: All layers being polymeric
- B32B 2264/102: Oxide or hydroxide
- B32B 2264/104: Oxysalt, e.g. carbonate, sulfate, phosphate or nitrate particles
- B32B 2264/108: Carbon, e.g. graphite particles
- B32B 2270/00: Resin or rubber layer containing a blend of at least two different polymers
- B32B 2307/202: Conductive
- B32B 2307/51: Elastic
- B32B 2307/54: Yield strength; Tensile strength
- B32B 2307/714: Inert, i.e. inert to chemical degradation, corrosion
- B32B 2597/00: Tubular articles, e.g. hoses, pipes
- C08F 214/262: {with fluorinated vinyl ethers}
- C08J 2327/18: Homopolymers or copolymers of tetrafluoroethylene
- C08K 2003/222: {Magnesia, i.e. magnesium oxide}
- C08L 2203/18: used for pipes
- C08L 2205/02: containing two or more polymers of the same C08L -group
- C08L 2312/00: Crosslinking
- F16L 11/04: made of rubber or flexible plastics
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- F16L: PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL

## Abstract

A thermoplastic resin composition including a fluororesin (A) and a crosslinked fluoroelastomer (B), wherein the fluororesin (A) is a copolymer that contains a chlorotrifluoroethylene unit and a tetrafluoroethylene unit and that has at least one functional group selected from a carbonyl group, an olefinic group and an amino group at a main chain terminal or side chain terminal of the polymer. The crosslinked fluoroelastomer (B) is obtained by subjecting a fluoroelastomer (b) to a dynamic crosslinking treatment along with a polyamine compound (c) having a thermal decomposition temperature of 210° C. or higher and a crosslinking accelerator (d) in the presence of the fluororesin (A) under conditions for melting the fluororesin (A). Also disclosed is a method for producing the thermoplastic composition, a molded article formed from the thermoplastic composition, and a laminated product including a resin layer formed from the thermoplastic composition.

## Claims

### Claim 1

A thermoplastic resin composition comprising a fluororesin (A) and a crosslinked fluoroelastomer (B),
wherein the fluororesin (A) is a copolymer that contains a chlorotrifluoroethylene unit and a tetrafluoroethylene unit and that has at least one functional group selected from the group consisting of a carbonyl group, an olefinic group and an amino group at a main chain terminal or side chain terminal of the polymer, and
wherein the crosslinked fluoroelastomer (B) is obtained by subjecting a fluoroelastomer (b) to a dynamic crosslinking treatment along with a polyamine compound (c) having a thermal decomposition temperature of 210° C. or higher and a crosslinking accelerator (d) in the presence of the fluororesin (A) under conditions for melting the fluororesin (A),
the crosslinking accelerator (d) is a quaternary ammonium salt,
the amount of the polyamine compound (c) is 0.5 to 15 parts by mass based on 100 parts by mass of the fluoroelastomer (b), and
the amount of the crosslinking accelerator (d) to be compounded is preferably 0.01 to 10 parts by mass based on 100 parts by mass of the fluoroelastomer (b).

### Claim 2 (depends on 1)

The thermoplastic resin composition according to claim 1, wherein the fluoroelastomer (b) is a vinylidene fluoride/tetrafluoroethylene/hexafluoropropylene-based fluoroelastomer.

### Claim 3 (depends on 1)

The thermoplastic resin composition according to claim 1, wherein the polyamine compound (c) is 2,2-bis[4-(4-aminophenoxy)phenyl]propane.

### Claim 4 (depends on 1)

A method for producing the thermoplastic resin composition according to claim 1, comprising:
subjecting the fluoroelastomer (b) to the dynamic crosslinking treatment along with the polyamine compound (c) having a thermal decomposition temperature of 210° C. or higher and the crosslinking accelerator (d) in the presence of the fluororesin (A) under conditions for melting the fluororesin (A).

### Claim 5 (depends on 1)

A molded article formed from the thermoplastic resin composition according to claim 1.

### Claim 6 (depends on 5)

A hose or tube for fuel, comprising the molded article according to claim 5.

### Claim 7 (depends on 1)

A laminated product comprising a thermoplastic resin layer (W) formed from the thermoplastic resin composition according to claim 1 and an elastomer layer (X) formed from an elastomer composition.

### Claim 8 (depends on 7)

The laminated product according to claim 7, wherein the elastomer composition contains at least one elastomer selected from the group consisting of an acrylonitrile-butadiene rubber, a hydrogenated acrylonitrile-butadiene rubber, a blend rubber between an acrylonitrile-butadiene rubber and a polyvinyl chloride, a blend rubber between an acrylonitrile-butadiene rubber and an acrylic rubber, a chlorinated polyethylene, a fluoroelastomer, an epichlorohydrin rubber, an ethylene-propylene rubber, a chlorosulfonated polyethylene rubber, a silicone rubber and an acrylic rubber.

### Claim 9 (depends on 7)

The laminated product according to claim 7, wherein the elastomer composition contains at least one compound selected from the group consisting of an onium salt, an amine compound and an epoxy resin.

### Claim 10 (depends on 7)

A hose or tube for fuel, comprising the laminated product according to claim 7.