Hrl Laboratories, LLC

Gm Global Technolgoy Operations, Inc.

The Boeing Company

Kevin J Drummey

Ashley M Dustin

Andrew Paul Nowak

Adam Franklin Gross

April Rose Rodriguez

Anthony L Smith

Gregory Phillip Nowak

Michael Jared Ventuleth

Shanying Cui

Phuong Bui

Adhesive formulations for forming a fluorinated poly(imide-phthalonitrile) thermoset polymer are provided. Such an adhesive formulation may comprise a fluorinated imide-phthalonitrile oligomer having Formula IV wherein Ris an unsubstituted or substituted aryl group and does not comprise an ether group; Ris an unsubstituted or substituted aryl group and does not comprise an ether group; at least one of Rand Rcomprises a fluorine substituent; and n has a value of from 1 to 30.

Fluorinated poly(imide-phthalonitrile) adhesive formulations and related methods

Some variations provide a polyoxalamide polymer comprising: one or more first segments containing at least one repeat unit that includes (i) a branched, aliphatic hydrocarbon species and (ii) first amide groups at internal ends of the repeat unit, wherein the first amide groups are part of oxalamide groups; one or more polymer end groups containing second amide groups that are each covalently bonded directly to one of the first amide groups, wherein the second amide groups are also part of the oxalamide groups, and wherein the oxalamide groups contain —N—C(═O)—C(—O)—N-sequences; and a reacted form of one or more multifunctional amine chain extenders or crosslinkers with an amine functionality of 3 or greater. The polyoxalamide polymer may be present in a lens, a window, a coating, or a film, for example. The polyoxalamide polymer may have UV transparency, visual transparency, NIR transparency, MWIR transparency, and/or LWIR transparency.

Durable, broadband-transparent polyoxalamide polymers and methods of making and using the same

Some variations provide an optic (such as an optical lens or an optical window) comprising at least 1 wt % of a polyoxalamide, wherein the optic is characterized by at least 40% average transmission of infrared radiation, and wherein the polyoxalamide comprises: first segments containing at least one repeat unit that includes (i) a branched, aliphatic hydrocarbon species and (ii) first amide groups at internal ends of the repeat unit, wherein the first amide groups are part of oxalamide groups; polymer end groups containing second amide groups that are each covalently bonded directly to one of the first amide groups, wherein the second amide groups are also part of the oxalamide groups, and wherein the oxalamide groups contain —N—C(═O)—C(═O)—N— sequences; and a reacted form of multifunctional amine chain extenders or crosslinkers with an amine functionality of 3 or greater. Methods of making and using the optic are described.

Durable, broadband-transparent polyoxalamide- based optics and methods of making and using the same

Phthalonitrile adhesive formulations are provided. Such an adhesive formulation may comprise an etherimide-phthalonitrile oligomer having formula

Poly(etherimide-phthalonitrile) adhesives and related methods

Provided herein are phthalonitrile adhesive formulations and methods of making and using the adhesive formulations. An illustrative adhesive formulation comprises a phthalonitrile additive selected from a group consisting of 1,2-dicyanobenzene; a derivative of 1,2-dicyanobenzene; and combinations thereof; a bisphthalonitrile compound; and a curing agent; wherein the phthalonitrile additive does not comprise an ether functional group and does not comprise a thioether functional group.

Phthalonitrile adhesive formulations and related methods

The disclosed technology provides improved thermoset vitrimers. It has been discovered that by incorporating adaptable dynamic groups along the polymer backbone, along with permanent, non-dynamic crosslinking points, an improved thermoset vitrimer is generated. In some variations, a thermoset vitrimer comprises: a linear polymer backbone containing associative dynamic covalently bonded species; a crosslinked network containing non-dynamic branch points; and non-dynamic species between non-dynamic branch points and terminal ends of the linear polymer backbone. Some methods comprise: reacting a linear prepolymer with an amine-containing species to form an amine-terminated linear prepolymer; reacting the amine-terminated linear prepolymer with an isocyanate-containing species to form an isocyanate-endcapped linear prepolymer; mixing the isocyanate-endcapped linear prepolymer with a reactive crosslinking agent having a crosslinking functionality of at least 3; and curing the isocyanate-endcapped linear prepolymer with the reactive crosslinking agent, thereby forming a thermoset vitrimer. Experimentally produced thermoset vitrimers demonstrate the ability for self-repair at elevated temperature.

Adaptable thermoset polymers with internal dynamic bonds, and methods of making and using the same

Some variations provide a polysulfide-based copolymer containing first repeat units comprising S-derived sulfur atoms bonded via sulfur-sulfur bonds; and second repeat units comprising an organic, non-aromatic thiol molecule. Other variations provide a polysulfide-based copolymer containing first repeat units comprising S-derived sulfur atoms bonded via sulfur-sulfur bonds; and second repeat units comprising an organic, non-aromatic unsaturated molecule, wherein the polysulfide-based copolymer has a total sulfur concentration of about 10 wt % or greater. Other variations provide a polysulfide-based copolymer containing first repeat units comprising S-derived sulfur atoms bonded via sulfur-sulfur bonds; second repeat units comprising an organic, non-aromatic thiol molecule; and third repeat units comprising an organic, non-aromatic unsaturated molecule. Other variations provide a polysulfide-based copolymer containing first repeat units comprising S-derived sulfur atoms bonded via sulfur-sulfur bonds; and second repeat units comprising an organic, non-aromatic thioether molecule. The disclosed polysulfide-based copolymers provide broadband transparency, fracture toughness, fluid resistance, and low cost.

Broadband-transparent polysulfide-based copolymers

An aqueous precursor liquid for forming an anti-fouling heterophasic thermoset polymeric coating is provided. The precursor liquid includes a first fluorine-containing polyol precursor having a functionality &#x3e;about 2 that forms a fluorine-containing polymer component defining a first phase in the coating. The precursor liquid also includes a second precursor that forms a second component present as a second phase. The first phase can be a continuous phase and the second phase can be a discrete phase, or the second phase can be the continuous phase and the first phase can be the discrete phase. The discrete phase includes a plurality of domains each having an average size of &#x2265;to about 500 nm to &#x2264;to about 25,000 nm. A crosslinking agent, water, and optional acid or base are also present. Methods of making anti-fouling heterophasic thermoset polymeric coatings with such precursors are also provided.

Precursors for forming heterophasic anti-fouling polymeric coatings

An aqueous or water-borne precursor for forming an anti-fouling heterophasic thermoset polymeric coating is provided. The precursor includes a fluorine-containing polyol precursor having a functionality greater than about 2 that forms a branched fluorine-containing polymer component defining a continuous phase in the anti-fouling heterophasic thermoset polymeric coating. The precursor also includes a fluorine-free precursor that forms a fluorine-free component present as a plurality of domains each having an average size of greater than or equal about 100 nm to less than or equal about 5,000 nm defining a discrete phase within the continuous phase in the anti-fouling heterophasic thermoset polymeric coating. A crosslinking agent and water are also present. An emulsifier may also be included. Methods of making anti-fouling heterophasic thermoset polymeric coatings with such precursors are also provided.

Water-borne precursors for forming heterophasic anti-fouling, polymeric coatings having a fluorinated continuous phase with non-fluorinated domains

An aqueous or water-borne precursor for forming an anti-fouling heterophasic thermoset polymeric coating is provided. The precursor includes a fluorine-containing polyol precursor having a functionality &#x3e;about 2 that forms a branched fluorine-containing polymer component defining a continuous phase in the anti-fouling heterophasic thermoset polymeric coating. The precursor also includes a fluorine-free precursor that forms a fluorine-free component present as a plurality of domains each having an average size of &#x2265;about 100 nm to &#x2264;about 5,000 nm defining a discrete phase within the continuous phase in the anti-fouling heterophasic thermoset polymeric coating. A crosslinking agent and water are also present. An emulsifier may also be included. Methods of making anti-fouling heterophasic thermoset polymeric coatings with such precursors are also provided.

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Los Angeles, CA, United States of America

Kevin J Drummey