Patent · US10011685B2 · B2 · US

Polyarylether ketone imide adhesives

(11) Publication number

US10011685B2

(21) Application number

15/068,249

(22) Filing date

2016-03-11

(30) Priority date

2016-03-11

(43) Publication date

2018-07-03

(45) Date of grant

2018-07-03

(51) IPC

B29C 65/00; B29C 65/48; B29C 67/00; C08G 73/10; C08J 5/24; C08J 7/043; C08K 7/06; C08K 7/14; C08L 79/08; C09D 179/08; C09J 179/08; H01B 3/30

(52) CPC

C08G Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds: 73/1071, 2261/3442, 2261/45, 2261/60, 61/127, 73/105
B29C Shaping or joining of plastics; shaping of material in a plastic state, not otherwise provided for; after-treatment of the shaped products, e.g. repairing: 65/02, 65/4815, 65/483, 65/5057, 66/1122, 66/45, 66/71, 66/721, 66/7212, 66/7392, 66/73921, 66/7394, 66/742, 67/0081
B29K Indexing scheme associated with subclasses B29B, B29C or B29D, relating to moulding materials or to materials for {moulds, } reinforcements, fillers or preformed parts, e.g. inserts: 2063/00, 2079/085, 2105/06, 2105/167, 2307/04, 2309/08
B29L Indexing scheme associated with subclass B29C, relating to particular articles: 2031/3076, 2031/3082, 2031/3085
B33Y Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering: 10/00, 70/00, 70/10
C08J Working-up; general processes of compounding; after-treatment not covered by subclasses C08B, C08C, C08F, C08G or C08H: 2379/08, 5/24, 7/0427, 7/043, 7/047
C08K Use of inorganic or non-macromolecular organic substances as compounding ingredients: 7/02, 7/04, 7/06, 7/14
C08L Compositions of macromolecular compounds: 79/08
C09D Coating compositions, e.g. paints, varnishes or lacquers; filling pastes; chemical paint or ink removers; inks; correcting fluids; woodstains; pastes or solids for colouring or printing; use of materials therefor: 179/08
C09J Adhesives; non-mechanical aspects of adhesive processes in general; adhesive processes not provided for elsewhere; use of materials as adhesives: 165/00, 179/08

(73) Assignee

Boeing Co

(72) Inventors

Christopher H. CHILDERS; Gregg R. BOGUCKI; Christopher S. STEINMAN; Stephen R. Heinz

(54) Title

Polyarylether ketone imide adhesives

(57) Abstract

Aspects of the present disclosure generally describe polyarylether ketones and methods of use. In some aspects, a composition includes one or more polymers of formula (IV):

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Claims (37)

A composition comprising one or more polymers of formula (IV): wherein: X is selected from the group consisting of: and combinations thereof, Z is selected from the group consisting of: - H, and combinations thereof, wherein R′ is - H, halo, C1-C20 alkyl, cyano, or combinations thereof, R is selected from the group consisting of: and combinations thereof, L is selected from the group consisting of: - CH 2 -, - (CH 3) 2 C -, - O -, - S -, - SO 2 -, - CO -, and combinations thereof, Q is selected from the group consisting of: - S -, - SO 2 -, - (CF 3) 2 C -, - O -, - (CH 3) 2 C -, and combinations thereof, j is a positive integer, m is a positive integer, n is a positive integer, and q is a positive integer and the molecular weight of at least one of the one or more polymers is between about 50 kDa and about 150 kDa.
The composition of claim 1, wherein the molecular weight of at least one of the one or more polymers is between about 90 kDa and about 110 kDa.
The composition of claim 1, wherein the molecular weight of each moiety of the structure: does not exceed about 3 kDa.
The composition of claim 1, wherein a ratio of m to n is between about 1:1 and about 1:2.
The composition of claim 1, wherein a ratio of to is between about 1:1 and about 1:2.
The composition of claim 1, wherein the moiety: is greater than about 33 mol % of the molecular weight of at least one of the one or more polymers.
The composition of claim 6, wherein the moiety: is greater than about 50 mol % of at least one of the one or more polymers.
The composition of claim 1, wherein the composition has a glass transition temperature between about 135° C. and about 225° C.
The composition of claim 8, wherein the composition has a glass transition temperature between about 135° C. and about 190° C.
The composition of claim 1, wherein the composition has a melting temperature between about 200° C. and about 450° C.
The composition of claim 1, wherein at least one of the one or more polymers of formula (IV) is a block copolymer.
The composition of claim 11, wherein q is 1, m is an integer between about 1 and about 1,000, and n is an integer between about 1 and about 1,000.
The composition of claim 1, wherein at least one of the one or more polymers of formula (IV) is a random copolymer.
The composition of claim 13, wherein q is an integer between 2 and about 2,000, m is an integer between about 1 and about 1,000, and n is an integer between about 1 and about 1,000.
The composition of claim 1, wherein at least one of the one or more polymers of Formula (IV) comprises: the moiety: is about 17 mol % of the molecular weight of the polymer, R is j is 1, the moiety: is about 32 mol % of the molecular weight of the polymer, and X is and X is about 46 mol % of the molecular weight of the polymer.
The composition of claim 1, wherein at least one of the one or more polymers of Formula (IV) comprises: the moiety: is about 23 mol % of the molecular weight of the polymer, R is j is 1, the moiety: is about 29 mol % of the molecular weight of the polymer, the moiety: is about 24 mol % of the molecular weight of the polymer, and the moiety: is about 24 mol % of the molecular weight of the polymer.
The composition of claim 1, further comprising a fiber material.
The composition of claim 17, wherein the fiber material is selected from the group consisting of graphite, fiberglass, nylon, aramid polymers, spectra, and mixtures thereof.
A vehicle component including the composition of claim 1.
The vehicle component of claim 19, wherein the vehicle component is a tail cone, a panel, a coated lap joint between two or more panels, a wing-to-fuselage assembly, structural aircraft composite, fuselage body-joint or wing rib-to-skin joint.
A method comprising: using the composition of claim 1 as an adhesive.
A method of using the composition of claim 1, the method comprising: coating a surface with the composition of claim 1.
A method comprising: forming a three dimensional structure at least partially comprising the composition of claim 1.
The method of claim 23, wherein the three dimensional structure further comprises a reinforcement agent selected from the group consisting of glass, carbon fibers, chopped carbon fibers, carbon black, and carbon nanotubes.
The method of claim 23, wherein forming the three dimensional structure comprises fused filament fabrication and/or selective laser sintering.
A three dimensional structure comprising the composition of claim 1.
The three dimensional structure of claim 26, further comprising a reinforcing agent.
A method comprising: coating a first surface with the composition of claim 1 to form a coated surface; contacting the coated surface with a second surface; and heating the composition to above about 355° C.
The method of claim 28, wherein the first surface comprises a thermoplastic prepreg, thermoset prepreg, and/or metal.
The method of claim 29, wherein the first surface comprises a thermoplastic prepreg, and heating the composition to above about 355° C. consolidates the thermoplastic prepreg.
The method of claim 29, wherein the first surface and the second surface comprises a thermoplastic prepreg, and wherein heating the composition to above about 355° C. consolidates the thermoplastic prepreg of the first surface and the thermoplastic prepreg of the second surface.
The method of claim 29, further comprising coating the second surface with the composition of claim 1 to form a second coated surface.
The method of claim 28, wherein the first surface is a surface of a vehicle component, and the second surface is a surface of a vehicle component.
The composition of claim 1, wherein: the molecular weight of the moiety of the structure: does not exceed about 3 kDa; and a ratio of m to n is between about 1:1 and about 1:2.
The composition of claim 34, wherein the molecular weight of at least one of the one or more polymers is between about 90 kDa and about 110 kDa.
The composition of claim 35, wherein a ratio of to is between about 1:1 and about 1:2.
The composition of claim 36, wherein the composition has: a glass transition temperature between about 135° C. and about 190° C.; and a melting temperature between about 200° C. and about 450° C.

Description

Aspects of the present disclosure generally relate to polyarylether ketones and methods of use.

A vehicle, such as an aircraft, contains many components adhered to one another by adhesives and/or fasteners. Adhesives and fasteners must withstand chemical, thermal, and physical conditions experienced by the vehicle. Adhesives offer greater performance, better design efficiency, and lower weight as compared to fasteners used for connecting the vehicle/aircraft components to one another. In particular, thermosets chemically or physically join vehicle/aircraft components by co-cure or co-bonding processes. However, co-curing involves expensive, precision tooling to properly locate and maintain the vehicle components as well as control of the thermoset resin distribution throughout the curing process. Additionally, co-cured structures typically suffer thickness control issues and ply waviness due to undesirable viscosity of an adhesive. Alternatively, co-bonding involves less extensive tooling but adds the costly labor of surface preparation for the surfaces of the vehicle components to be joined.

Regarding thermoset materials, thermosets have components that are typically fabricated with a peel ply on the surfaces to be joined, which is removed prior to joining, coupled with a surface preparation process such as grit blasting, plasma etching, and or hand sanding of the surfaces to be joined, and followed by bonding of those surfaces with an adhesive. Adhesives are typically thermosets or thermoplastics, such as poly ether ketone ketone (PEKK) or poly ether ether ketone (PEEK).

Citations (9)

US4816556A
EP0210851A2
US4868271A
WO1989010049A2
US5260404A
US20150337082A1
WO2015177550A1
US20150337183A1
WO2015197618A1

Record as JSON

{
  "publication_number": "US10011685B2",
  "country": "US",
  "kind": "B2",
  "title": "Polyarylether ketone imide adhesives",
  "abstract": "Aspects of the present disclosure generally describe polyarylether ketones and methods of use. In some aspects, a composition includes one or more polymers of formula (IV):",
  "claims": [
    "1. A composition comprising one or more polymers of formula (IV): wherein: X is selected from the group consisting of: and combinations thereof, Z is selected from the group consisting of: - H, and combinations thereof, wherein R′ is - H, halo, C1-C20 alkyl, cyano, or combinations thereof, R is selected from the group consisting of: and combinations thereof, L is selected from the group consisting of: - CH 2 -, - (CH 3) 2 C -, - O -, - S -, - SO 2 -, - CO -, and combinations thereof, Q is selected from the group consisting of: - S -, - SO 2 -, - (CF 3) 2 C -, - O -, - (CH 3) 2 C -, and combinations thereof, j is a positive integer, m is a positive integer, n is a positive integer, and q is a positive integer and the molecular weight of at least one of the one or more polymers is between about 50 kDa and about 150 kDa.",
    "2. The composition of claim 1, wherein the molecular weight of at least one of the one or more polymers is between about 90 kDa and about 110 kDa.",
    "3. The composition of claim 1, wherein the molecular weight of each moiety of the structure: does not exceed about 3 kDa.",
    "4. The composition of claim 1, wherein a ratio of m to n is between about 1:1 and about 1:2.",
    "5. The composition of claim 1, wherein a ratio of to is between about 1:1 and about 1:2.",
    "6. The composition of claim 1, wherein the moiety: is greater than about 33 mol % of the molecular weight of at least one of the one or more polymers.",
    "7. The composition of claim 6, wherein the moiety: is greater than about 50 mol % of at least one of the one or more polymers.",
    "8. The composition of claim 1, wherein the composition has a glass transition temperature between about 135° C. and about 225° C.",
    "9. The composition of claim 8, wherein the composition has a glass transition temperature between about 135° C. and about 190° C.",
    "10. The composition of claim 1, wherein the composition has a melting temperature between about 200° C. and about 450° C.",
    "11. The composition of claim 1, wherein at least one of the one or more polymers of formula (IV) is a block copolymer.",
    "12. The composition of claim 11, wherein q is 1, m is an integer between about 1 and about 1,000, and n is an integer between about 1 and about 1,000.",
    "13. The composition of claim 1, wherein at least one of the one or more polymers of formula (IV) is a random copolymer.",
    "14. The composition of claim 13, wherein q is an integer between 2 and about 2,000, m is an integer between about 1 and about 1,000, and n is an integer between about 1 and about 1,000.",
    "15. The composition of claim 1, wherein at least one of the one or more polymers of Formula (IV) comprises: the moiety: is about 17 mol % of the molecular weight of the polymer, R is j is 1, the moiety: is about 32 mol % of the molecular weight of the polymer, and X is and X is about 46 mol % of the molecular weight of the polymer.",
    "16. The composition of claim 1, wherein at least one of the one or more polymers of Formula (IV) comprises: the moiety: is about 23 mol % of the molecular weight of the polymer, R is j is 1, the moiety: is about 29 mol % of the molecular weight of the polymer, the moiety: is about 24 mol % of the molecular weight of the polymer, and the moiety: is about 24 mol % of the molecular weight of the polymer.",
    "17. The composition of claim 1, further comprising a fiber material.",
    "18. The composition of claim 17, wherein the fiber material is selected from the group consisting of graphite, fiberglass, nylon, aramid polymers, spectra, and mixtures thereof.",
    "19. A vehicle component including the composition of claim 1.",
    "20. The vehicle component of claim 19, wherein the vehicle component is a tail cone, a panel, a coated lap joint between two or more panels, a wing-to-fuselage assembly, structural aircraft composite, fuselage body-joint or wing rib-to-skin joint.",
    "21. A method comprising: using the composition of claim 1 as an adhesive.",
    "22. A method of using the composition of claim 1, the method comprising: coating a surface with the composition of claim 1.",
    "23. A method comprising: forming a three dimensional structure at least partially comprising the composition of claim 1.",
    "24. The method of claim 23, wherein the three dimensional structure further comprises a reinforcement agent selected from the group consisting of glass, carbon fibers, chopped carbon fibers, carbon black, and carbon nanotubes.",
    "25. The method of claim 23, wherein forming the three dimensional structure comprises fused filament fabrication and/or selective laser sintering.",
    "26. A three dimensional structure comprising the composition of claim 1.",
    "27. The three dimensional structure of claim 26, further comprising a reinforcing agent.",
    "28. A method comprising: coating a first surface with the composition of claim 1 to form a coated surface; contacting the coated surface with a second surface; and heating the composition to above about 355° C.",
    "29. The method of claim 28, wherein the first surface comprises a thermoplastic prepreg, thermoset prepreg, and/or metal.",
    "30. The method of claim 29, wherein the first surface comprises a thermoplastic prepreg, and heating the composition to above about 355° C. consolidates the thermoplastic prepreg.",
    "31. The method of claim 29, wherein the first surface and the second surface comprises a thermoplastic prepreg, and wherein heating the composition to above about 355° C. consolidates the thermoplastic prepreg of the first surface and the thermoplastic prepreg of the second surface.",
    "32. The method of claim 29, further comprising coating the second surface with the composition of claim 1 to form a second coated surface.",
    "33. The method of claim 28, wherein the first surface is a surface of a vehicle component, and the second surface is a surface of a vehicle component.",
    "34. The composition of claim 1, wherein: the molecular weight of the moiety of the structure: does not exceed about 3 kDa; and a ratio of m to n is between about 1:1 and about 1:2.",
    "35. The composition of claim 34, wherein the molecular weight of at least one of the one or more polymers is between about 90 kDa and about 110 kDa.",
    "36. The composition of claim 35, wherein a ratio of to is between about 1:1 and about 1:2.",
    "37. The composition of claim 36, wherein the composition has: a glass transition temperature between about 135° C. and about 190° C.; and a melting temperature between about 200° C. and about 450° C."
  ],
  "description_excerpt": "Aspects of the present disclosure generally relate to polyarylether ketones and methods of use.\n\nA vehicle, such as an aircraft, contains many components adhered to one another by adhesives and/or fasteners. Adhesives and fasteners must withstand chemical, thermal, and physical conditions experienced by the vehicle. Adhesives offer greater performance, better design efficiency, and lower weight as compared to fasteners used for connecting the vehicle/aircraft components to one another. In particular, thermosets chemically or physically join vehicle/aircraft components by co-cure or co-bonding processes. However, co-curing involves expensive, precision tooling to properly locate and maintain the vehicle components as well as control of the thermoset resin distribution throughout the curing process. Additionally, co-cured structures typically suffer thickness control issues and ply waviness due to undesirable viscosity of an adhesive. Alternatively, co-bonding involves less extensive tooling but adds the costly labor of surface preparation for the surfaces of the vehicle components to be joined.\n\nRegarding thermoset materials, thermosets have components that are typically fabricated with a peel ply on the surfaces to be joined, which is removed prior to joining, coupled with a surface preparation process such as grit blasting, plasma etching, and or hand sanding of the surfaces to be joined, and followed by bonding of those surfaces with an adhesive. Adhesives are typically thermosets or thermoplastics, such as poly ether ketone ketone (PEKK) or poly ether ether ketone (PEEK).",
  "cpc": [
    "C08G 73/1071",
    "B29C 65/02",
    "B29C 65/4815",
    "B29C 65/483",
    "B29C 65/5057",
    "B29C 66/1122",
    "B29C 66/45",
    "B29C 66/71",
    "B29C 66/721",
    "B29C 66/7212",
    "B29C 66/7392",
    "B29C 66/73921",
    "B29C 66/7394",
    "B29C 66/742",
    "B29C 67/0081",
    "B29K 2063/00",
    "B29K 2079/085",
    "B29K 2105/06",
    "B29K 2105/167",
    "B29K 2307/04",
    "B29K 2309/08",
    "B29L 2031/3076",
    "B29L 2031/3082",
    "B29L 2031/3085",
    "B33Y 10/00",
    "B33Y 70/00",
    "B33Y 70/10",
    "C08G 2261/3442",
    "C08G 2261/45",
    "C08G 2261/60",
    "C08G 61/127",
    "C08G 73/105",
    "C08J 2379/08",
    "C08J 5/24",
    "C08J 7/0427",
    "C08J 7/043",
    "C08J 7/047",
    "C08K 7/02",
    "C08K 7/04",
    "C08K 7/06",
    "C08K 7/14",
    "C08L 79/08",
    "C09D 179/08",
    "C09J 165/00",
    "C09J 179/08"
  ],
  "ipc": [
    "B29C 65/00",
    "B29C 65/48",
    "B29C 67/00",
    "C08G 73/10",
    "C08J 5/24",
    "C08J 7/043",
    "C08K 7/06",
    "C08K 7/14",
    "C08L 79/08",
    "C09D 179/08",
    "C09J 179/08",
    "H01B 3/30"
  ],
  "assignees": [
    "Boeing Co"
  ],
  "inventors": [
    "Christopher H. CHILDERS",
    "Gregg R. BOGUCKI",
    "Christopher S. STEINMAN",
    "Stephen R. Heinz"
  ],
  "filing_date": "2016-03-11",
  "publication_date": "2018-07-03",
  "grant_date": "2018-07-03",
  "priority_date": "2016-03-11",
  "application_number": "US-201615068249-A",
  "family_id": "59776689",
  "cited_by_count": 113,
  "citations": [
    "US4816556A",
    "EP0210851A2",
    "US4868271A",
    "WO1989010049A2",
    "US5260404A",
    "US20150337082A1",
    "WO2015177550A1",
    "US20150337183A1",
    "WO2015197618A1"
  ]
}

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