Fibers sized with polyethereketoneketones

• US 9,657,437 B2
• Filed: 08/06/2014
• Issued: 05/23/2017
• Est. Priority Date: 02/05/2009
• Status: Active Grant

• Current Assignee: Arkema France (Arkema)
• Original Assignee: Arkema Incorporated (Arkema)
• Inventors: Bertelo, Christopher A., O'Brien, Gregory S.
• Primary Examiner(s): PAK, HANNAH J
• Application Number:
  US14/452,657
• Publication Number:
  US 20140349533A1
• Time in Patent Office: 1,021 Days
• Field of Search: 524540
• CPC Class Codes: C03C 25/26 Macromolecular compounds or prepolymers
• CPC Class Codes: C03C 25/32 obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08G 2650/40 containing ketone groups, e.g. polyarylethylketones, PEEK or PEK
• CPC Class Codes: C08J 2371/00 Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain of polyacetals C08J2359/00; of epoxy resins C08J2363/00; of polythioether-ethers C08J2381/02; of polyethersulfones C08J2381/06; Derivatives of such polymers
• CPC Class Codes: C08J 5/06 using pretreated fibrous materials
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08K 7/02 Fibres or whiskers
• CPC Class Codes: C08K 7/04 inorganic
• CPC Class Codes: C08K 7/14 Glass
• CPC Class Codes: C08L 29/10 Homopolymers or copolymers of unsaturated ethers C08L35/08 takes precedence
• CPC Class Codes: C08L 29/12 Homopolymers or copolymers of unsaturated ketones
• CPC Class Codes: C08L 71/00 Compositions of polyethers obtained by reactions forming an ether link in the main chain of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 171/00 Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain based on polyacetals C09D159/00; based on epoxy resins C09D163/00; based on polythioether-ethers C09D181/02; based on polyethersulfones C09D181/06; Coating compositions based on derivatives of such polymers
• CPC Class Codes: D06M 15/39 Aldehyde resins; Ketone resins; Polyacetals
• CPC Class Codes: D06M 15/53 Polyethers polyacetals D06M15/39
• CPC Class Codes: D06M 2101/00 Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
• CPC Class Codes: D06M 2101/40 Fibres of carbon
• CPC Class Codes: D06M 2200/40 Reduced friction resistance, lubricant properties; Sizing compositions
• CPC Class Codes: D06M 23/08 Processes in which the treating agent is applied in powder or granular form adhesives for multi-layer textile fabrics D06M17/00
• CPC Class Codes: Y10T 428/26 Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
• CPC Class Codes: Y10T 428/27 : Web or sheet containing structurally defined element or component, the element or component having a specified weight per unit area [e.g., gms/sq cm, lbs/sq ft, etc.]
• CPC Class Codes: Y10T 428/2916 : including boron or compound thereof [not as steel]
• CPC Class Codes: Y10T 428/2918 : including free carbon or carbide or therewith [not as steel]
• CPC Class Codes: Y10T 428/2933 : Coated or with bond, impregnation or core
• CPC Class Codes: Y10T 428/294 : including metal or compound thereof [excluding glass, ceramic and asbestos]
• CPC Class Codes: Y10T 428/2942 : Plural coatings
• CPC Class Codes: Y10T 428/2947 : Synthetic resin or polymer in plural coatings, each of different type
• CPC Class Codes: Y10T 428/2964 : Artificial fiber or filament
• CPC Class Codes: Y10T 428/2967 : Synthetic resin or polymer
• CPC Class Codes: Y10T 428/2969 : Polyamide, polyimide or polyester
• CPC Class Codes: Y10T 428/31645 : Next to addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 442/2402 : Coating or impregnation specified as a size

Abstract

Fibers sized with a coating of amorphous polyetherketoneketone are useful in the preparation of reinforced polymers having improved properties, wherein the amorphous polyetherketoneketone can improve the compatibility of the fibers with the polymeric matrix.

Claims

1. A sized fiber comprising a fiber having a coating of amorphous polyetherketoneketone, said coating comprising about 0.01 to about 10% by weight of the amount of coating in the sized fiber and having a thickness of about 1 micron to about 50 microns, wherein said coating surrounds said fiber surfaces,

and wherein the amorphous polyetherketoneketone is comprised of repeating units represented by formulas I and II:

-A-C(═

O)—

B—

C(═

O)—

 

 

I

-A-C(═

O)-D-C(═

O)—

 

 

II

wherein A is a p,p′

-Ph-O-Ph- group, Ph is a phenylene radical, B is p-phenylene, and D is m-phenylene and the isomer ratio of formula I;

formula II (T;

I) ranges from about 55;

45 to about 65;

35.

2. The sized fiber of claim 1, wherein said fiber is a monofilament.

3. The sized fiber of claim 1, wherein said fiber is a multifilament.

4. The sized fiber of claim 1, wherein said fiber has a diameter of about 50 microns to about 1 mm.

5. The sized fiber of claim 1, wherein said fiber is selected from the group consisting of glass fibers, carbon fibers, mineral fibers, metal fibers and polymeric fibers.

6. The sized fiber of claim 1, where said fiber is made from one or more components selected from the group consisting of glass, graphite fibers, polyamides, polyolefins, polyaramids, polyesters, poly(p-phenylene-2,6-benzobisoxazole)(PBO), iron, steel, aluminum, aluminum alloys, copper, titanium, nickel, gold, silver, mineral wool, rock wool, stone wool, basalt fibers, alumina fibers, beryllia fibers, magnesia fibers, thoria fibers, zirconia fibers, silicon carbide fibers, quartz fibers, boron fibers, and asbestos fibers.

7. A reinforced polymer comprising a polymer matrix and sized fibers of claim 1.

8. The reinforced polymer of claim 7, wherein said polymer matrix is comprised of a one or more thermoplastics selected from the group consisting of polyaryletherketones (PAEK), polyetheretherketone (PEEK), polyetherketoneketone (PEKK), polyetheretheretherketone (PEEEK), polyetheretherketoneketone (PEEKK), polyetherketoneetheretherketone (PEKEKK), polyetherketoneketoneketone (PEKKK)), polyimides, polyetherimides, polyamideimides, polysulfones, polyethersulfones, polyarylethers, polycarbonates, liquid crystal polymers, polyphenylene sulfides, polyarylenes (polyphenylenes), polyamides, polyphthalamides, and polyaromatic esters.

9. The reinforced polymer of claim 7, wherein said polymer matrix is comprised of a crystalline poly(aryletherketone).

11. A thermoplastic pellet comprising the sized fibers claim 1, said fibers having a length and a diameter such that said fiber length is at least 10 times the fiber diameter, and one or more thermoplastics selected from the group consisting of polyaryletherketones (PAEK), polyetheretherketone (PEEK), polyetherketoneketone (PEKK), polyetheretheretherketone (PEEEK), polyetheretherketoneketone (PEEKK), polyetherketoneetheretherketone (PEKEKK), polyetherketoneketoneketone (PEKKK)), polyimides, polyetherimides, polyamideimides, polysulfones, polyethersulfones, polyarylethers, polycarbonates, liquid crystal polymers, polyphenylene sulfides, polyarylenes (polyphenylenes), polyamides, polyphthalamides, and polyaromatic esters.

10. A pellet comprising sized fibers and one or more thermoplastics selected from the group consisting of polyaryletherketones (PAEK), polyetheretherketone (PEEK), polyetherketoneketone (PEKK), polyetheretheretherketone (PEEEK), polyetheretherketoneketone (PEEKK), polyetherketoneetheretherketone (PEKEKK), polyetherketoneketoneketone (PEKKK)), polyimides, polyetherimides, polyamideimides, polysulfones, polyethersulfones, polyarylethers, polycarbonates, liquid crystal polymers, polyphenylene sulfides, polyarylenes (polyphenylenes), polyamides, polyphthalamides, and polyaromatic esters;

wherein said sized fibers comprise a fiber having a coating of amorphous polyetherketoneketone, said coating comprising about 0.01 to about 10% by weight of the amount of coating in the sized fibr and having a thickness of about 1 micron to about 50 microns, wherein said coating surrounds said fiber surfaces,

and wherein the amorphous polyetherketoneketone is comprised of repeating units represented by formulas I and II;

-A-C(═

O)—

B—

C(═

O)—

 

 

I

-A-C(═

O)-D-C(═

O)—

 

 

II

wherein A is a p,p′

-Ph-O-Ph- group, Ph is a phenylene radical, B is p-phenylene, and D is m-phenylene and the isomer ratio of formula I;

formula II (T;

I) ranges from about 55;

45 to about 65;

35.

12. A yarn, thread, strand roving, mat, mesh, scrim, woven fabric, or non-woven fabric comprising sized fibers, said sized fibers comprising a fiber having a coating of amorphous polyetherketoneketone, said coating comprising about 0.01 to about 10% by weight of the amount of coating in the sized fiber and having a thickness of about 1 micron to about 50 microns, wherein said coating surrounds said fiber surfaces,

and wherein the amorphous polyetherketoneketone is comprised of repeating units represented by formulas I and II:

-A-C(═

O)—

B—

C(═

O)—

 

 

I

-A-C(═

O)-D-C(═

O)—

 

 

II

wherein A is a p,p′

Ph-O-Ph- group, Ph is a phenylene radical, B is p-phenylene, and D is m-phenylene and the isomer ratio of formula I;

formula II (T;

I) ranges from about 55;

45 to about 65;

35.

13. A method of making a sized fiber, said method comprising coating a fiber with a sizing composition comprising amorphous polyetherketoneketone, said coating comprising about 0.01 to about 10% by weight of the amount of coating in the sized fiber and having a thickness of about 1 micron to about 50 microns, wherein said coating surrounds said fiber surfaces, and wherein the amorphous polyetherketoneketone is comprised of repeating units represented by formulas I and II:

-A-C(═

O)—

B—

C(═

O)—

 

 

I

-A-C(═

O)-D-C(═

O)—

 

 

II

wherein A is a p,p′

-Ph-O-Ph- group, Ph is a phenylene radical, B is p-phenylene, and D is m-phenylene and the isomer ratio of formula I;

formula II (T;

I) ranges from about 55;

45 to about 65;

35.

14. The method of making the sized fiber of claim 13, where the fiber is in the form of twisted yarns, threads, strands, rovings, mats, meshes, scrims, woven fabric, or non-woven fabric and is sized with the amorphous polyetherketoneketone, thereby providing the sized fiber.