Phthalonitrile-based high temperature resistive inks

Patent metadata

Field	Value
Publication number	US-12187908-B2
Application number	US-202117451403-A
Country	US
Kind code	B2
Filing date	Oct 19, 2021
Priority date	Oct 20, 2020
Publication date	Jan 7, 2025
Grant date	Jan 7, 2025

Abstract

Resistive inks and method of making resistive inks that utilize a phthalonitrile resin as a curable component in the inks are disclosed. In one example, a resistive ink is provided. The resistive ink comprises a solvent, a thermally-curable phthalonitrile-based resin dissolved in the solvent, and one or more conductive fillers. In some examples, the phthalonitrile resin can comprise a B-staged material.

First claim

The invention claimed is:

1. A resistive ink, comprising:
a solvent;
a curable phthalonitrile resin dissolved in the solvent; and
one or more conductive fillers.

2. The resistive ink of claim 1 , wherein the phthalonitrile resin comprises a ketone, an ether, a urethane, a urea, an amide, an imide, an ester, a sulfone, an oxamide, a benzoxazine, a maleimide, or a combination of two or more thereof.

3. The resistive ink of claim 1 , wherein the phthalonitrile resin comprises a polyether ether ketone (PEEK) resin.

4. The resistive ink of claim 1 , wherein the solvent comprises 2-phenoxyethanol, N-methyl-2-pyrrolidone (NMP), m-cresol, benzyl alcohol, diphenyl ether, acetone, methyl ethyl ketone (MEK), methyl n-propyl ketone (MPK), methyl isobutyl ketone (MIBK), tetrahydrofuran (THF), n-butyl acetate, chloroform, methylene chloride, carbon tetrachloride, toluene, trichloroethylene, isopropanol, diethyl ether, dimethyl sulfoxide, dimethyl formamide, xylene or a combination of two or more thereof.

5. The resistive ink of claim 1 , wherein the conductive filler comprises activated carbon, graphite, short-chopped carbon fiber, nickel, silver, copper, gold, platinum, iridium, stainless steel, iron, titanium, zinc, or a combination of two or more thereof.

6. The resistive ink of claim 1 , further comprising a dispersant, a flow agent, a cure promoter, a surfactant, a flame retardant, a viscosity modifier, or a combination of two or more thereof.

7. The resistive ink of claim 1 , further comprising a metallic catalyst, an amino-functional catalyst, a phenolic-functional catalyst, or a combination of two or more thereof.

8. The resistive ink of claim 1 , further comprising an organic filler comprising polyether ether ketone (PEEK), polyether ketone ketone (PEKK), a polyetherimide, or a combination of two or more thereof.

9. A method of making a resistive ink, the method comprising:
mixing a phthalonitrile resin, a conductive filler, and a solvent to dissolve the phthalonitrile resin in the solvent and to form the resistive ink.

10. The method of claim 9 , further comprising, prior to mixing the phthalonitrile resin, applying heat to initiate a polymerization of the phthalonitrile resin, and quenching polymerization of the phthalonitrile resin before completion of polymerization to form a B-staged phthalonitrile resin.

11. The method of claim 10 , wherein applying heat to initiate polymerization of the phthalonitrile resin comprises heating to a temperature of 200° C. or greater to quick set the phthalonitrile resin.

12. The method of claim 9 , further comprising grinding the phthalonitrile resin prior to mixing.

13. The method of claim 9 , wherein mixing the phthalonitrile resin and the solvent comprises mixing via one or more of a shaker table, an overhead mixer, magnetic stirring, and a centrifugal mixer.

14. The method of claim 9 , wherein mixing the conductive filler in the solvent comprises mixing for between 5 minutes to 90 minutes.

15. The method of claim 9 , further comprising adding additional solvent after mixing the conductive filler, adding additional conductive filler, and then adding additional solvent.

16. The method of claim 9 , wherein the phthalonitrile resin comprises a polyether ether ketone (PEEK) resin.

17. A method of making a high temperature resistive film and/or cured adhesive, the method comprising:
applying a resistive ink comprising a phthalonitrile resin, a solvent, and one or more conductive fillers on a substrate;
evaporating the solvent from the resistive ink; and
curing the phthalonitrile resin on the substrate by activating a catalyst contained in the resistive ink.

18. The method of claim 17 , wherein applying the resistive ink comprises applying via a doctor blade, a screen printing process, a roll-to-roll process, or a combination thereof.

19. The method of claim 17 , wherein evaporating the solvent comprises evaporating the solvent via a hot plate, oven, a heat lamp, an infrared lamp, or a combination of two or more thereof and heating for 1 min to 3 min.

20. The method of claim 17 , wherein curing the phthalonitrile resin comprises thermally curing the phthalonitrile resin at a temperature within a range of 150° C. to 400° C.

Assignees

• Boeing Co

Inventors

• Dustin Ashley M
• Guan Xin
• Ventuleth Michael J
• Nowak Andrew P
• Alam Shahriar
• Fors Stella

Classifications

• C09D11/101

  Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing · CPC title

• C09D135/04

  Homopolymers or copolymers of nitriles (C09D135/06, C09D135/08 take precedence) · CPC title

• C09D11/102

  containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds · CPC title

• C08K3/04

  Carbon · CPC title

• C08G73/024

  Polyamines containing oxygen in the form of ether bonds in the main chain · CPC title