3m Innovative Properties Company

Benjamin J Anderson

Tatsuo Fukushi

Gregg D Dahlke

Michael H Mitchell

Wendy L Thompson

Ilya Gorodisher

Gregory P Sorenson

Jeremy M Higgins

Jay R Lomeda

Amit J Patel

The present disclosure provides a polymerizable composition. The polymerizable composition includes a phthalonitrile resin, a curative, and a polyoxometalate of Formula I: H[XMO] (I). In Formula (I), M is W or Mo, n is 1 to 6, and X is a heteroatom selected from P, Si, S, Ge, As, Te, or Se. The present disclosure also provides an article. The article includes a polymerization product of the polymerizable composition. Additionally, a method is provided. The method includes mixing a polyoxometalate of Formula I with at least one of a curative or phthalonitrile resin and mixing at least a portion of the curative with at least a portion of the phthalonitrile, thereby forming a polymerizable composition. The method further comprises subjecting the polymerizable composition to a temperature of 180° C. to 250° C., to form an at least partially polymerized article and subjecting the at least partially polymerized article to a temperature of 300° C. to 350° C. to complete polymerization of the article.

Polymerizable compositions including a phthalonitrile resin and a polyoxometalate, articles, and methods

Described herein are fluoropolymer compositions comprising a bis phthalonitrile-containing compound. In one embodiment, the bis phthalonitrile-containing compound is used to crosslink a dehydrohalogenated polymer, and optionally with a polyhydroxy curative. In another embodiment, the bis phthalonitrile-containing compound is added to a composition comprising (i) a fluorinated elastomeric gum, wherein the fluorinated elastomeric gum comprises a fluoropolymer having a cure-site and (ii) a peroxide curing system.

Curable fluoropolymer compositions comprising bis phthalonitrile-containing compound and cured articles therefrom

The present disclosure provides a resin blend containing a blend of a phthalonitrile resin and a thiadiazole substituted phthalonitrile compound. The present disclosure also provides an article including a polymerization product of such a resin blend. Further, a thiadiazole substituted phthalonitrile compound and an article including a polymerization product of the compound are provided. The present disclosure additionally provides a method of making a thiadiazole substituted phthalonitrile compound. Certain thiadiazole substituted phthalonitrile compounds can act as curatives for the phthalonitrile resin.

Resin blends including phthalonitrile resin and thiadiazole substituted phthalonitrile compound, articles, compounds, and methods

Described herein are fluoropolymer compositions comprising a compound of Formula (I) wherein Xis selected from O or S; L is a divalent linking group comprising at least one aromatic ring; O and Xcomprises a carbon-carbon double bond. In one embodiment, the phthalonitrile-containing compound is added to a composition comprising (i) a fluorinated elastomeric gum, wherein the fluorinated elastomeric gum comprises a fluoropolymer having a cure-site and (ii) a peroxide curing system. 

Curable fluoropolymer compositions comprising a compound containing a phthalonitrile and an olefinic bond and cured articles therefrom

Described herein are fluoropolymer compositions comprising a compound of Formula I wherein Xis selected from O or S; L is a divalent linking group comprising at least one aromatic ring; and Xis selected from the group consisting of a hydroxyl group, an amino group, a thiol group, and a nitrile group. In one embodiment, the phthalonitrile-containing compound is used to crosslink a dehydrohalogenated polymer, and optionally with a polyhydroxy curative. In another embodiment, the phthalonitrile-containing compound is added to a composition comprising (i) a fluorinated elastomeric gum, wherein the fluorinated elastomeric gum comprises a fluoropolymer having a cure-site and (ii) a peroxide curing system. 

Curable fluoropolymer compositions comprising a compound containing a phthalonitrile and a nucleophilic functional group and cured articles therefrom

Resins are provided including bisphenol M diphthalonitrile ether resin or bisphenol P diphthalonitrile either resin. Compositions are also provided, including a primary amine curative and the bisphenol M diphthalonitrile ether resin or the bisphenol P diphthalonitrile either resin. Further, polymerized products are provided of the bisphenol M diphthalonitrile ether resin or the bisphenol P diphthalonitrile either resin. In addition, a method of making a polymerized network is provided. A two component system is further provided, including a curative in one of the components and the bisphenol M diphthalonitrile ether resin or the bisphenol P diphthalonitrile either resin in the other component. In addition, a resin blend is provided, including a blend of at least two of bisphenol M diphthalonitrile ether resin, bisphenol P diphthalonitrile either resin, or bisphenol T diphthalonitrile ether resin.

Bisphenol M diphthalonitrile ether resin, bisphenol P diphthalonitrile ether resin, methods of making same, resin blends, and two component systems

The present disclosure provides a resin blend. The resin blend includes at least one diluent containing a single phthalonitrile functional group and at least one diphthalonitrile resin. Also provided are prepregs including the resin blend impregnated into continuous reinforcing fibers or a cloth. Similarly, the present disclosure provides a molding compound including chopped reinforcing fibers distributed in the resin blend. An article is also provided, which includes polymerization product of the resin blend. An alternative article includes a substrate and a layer of the resin blend disposed on the substrate. The diluent typically improves processability of the resin blend and lowers the softening temperature of the polymerization product of the resin blend.

Resin blends containing a phthalonitrile reactive diluent and a diphthalonitrile resin, prepregs, and articles

The present disclosure provides a resin blend containing a blend of a first phthalonitrile resin, a filler, and a bisphenol M diphthalonitrile ether resin. Suitable fillers include at least one of nanoparticles, microparticles, or fibers. The present disclosure also provides an article including a polymerization product of such a resin blend. The resin blends can be prepared at lower temperatures than phthalonitrile resin blends without a bisphenol M diphthalonitrile ether resin.

Bisphenol M diphthalonitrile ether resin blends including a filler, and articles

A resin blend is provided including a blend of resorcinol diphthalonitrile ether resin and a bisphenol M diphthalonitrile ether resin. Another resin blend is provided including a blend of resorcinol diphthalonitrile ether resin and a bisphenol T diphthalonitrile ether resin. The resin blends prior to cure have more favorable processing and curing properties compared to the resorcinol diphthalonitrile resin alone, enabling greater ease in manufacturing.

Resin blends of resorcinol diphthalonitrile ether with bisphenol M diphthalonitrile ether and/or bisphenol T diphthalonitrile ether

A resin blend is provided including a blend of a benzoxazine resin and a phthalonitrile resin. The benzoxazine/phthalonitrile resin blends prior to cure have more favorable processing and curing properties compared to the phthalonitrile resins alone, enabling greater ease in manufacturing.

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Eden Prairie, MN, United States of America

Benjamin J Anderson