Abstract: Polyhemiaminal (PHA) and polyhexahydrotriazine (PHT) materials are modified by 1,4 conjugate addition chemical reactions to produce a variety of molecular architectures comprising pendant groups and bridging segments. The materials are formed by a method that includes heating a mixture comprising solvent(s), paraformaldehyde, aromatic amine groups, aliphatic amine Michael donors, and Michael acceptors, such as acrylates. The reaction mixtures may be used to prepare polymer pre-impregnated materials and composites containing PHT matrix resin.

Abstract: Materials and methods are described herein that include forming a porous polymer network with antimicrobial and antifouling properties. The antifouling portion may be a polymer, such as polyethylene glycol, and the antimicrobial portion may be a metal, or a different cationic species, such as a quaternary ammonium salt. The method generally includes forming a reaction mixture comprising a formaldehyde, a bridging group, and moieties with antifouling and antimicrobial properties.

Abstract: Methods of forming nanoporous materials are described herein that include forming a polymer network with a chemically removable portion. The chemically removable portion may be polycarbonate polymer that is removable on application of heat or exposure to a base, or a polyhexahydrotriazine (PHT) or polyhemiaminal (PHA) polymer that is removable on exposure to an acid. The method generally includes forming a reaction mixture comprising a formaldehyde, a solvent, a primary aromatic diamine, and a diamine having a primary amino group and a secondary amino group, the secondary amino group having a base-reactive substituent, and heating the reaction mixture to a temperature of between about 50 deg C. and about 150 deg C. to form a polymer. Removing any portion of the polymer results in formation of nanoscopic pores as polymer chains are decomposed, leaving pores in the polymer matrix.

Abstract: This disclosure describes new compositions and methods related to photoresponsive poly(hexahydrotriazines) and related polymers.

Abstract: Methods of forming nanoporous materials are described herein that include forming a polymer network with a chemically removable portion. The chemically removable portion may be polycarbonate polymer that is removable on application of heat or exposure to a base, or a polyhexahydrotriazine (PHT) or polyhemiaminal (PHA) polymer that is removable on exposure to an acid. The method generally includes forming a reaction mixture comprising a formaldehyde, a solvent, a primary aromatic diamine, and a diamine having a primary amino group and a secondary amino group, the secondary amino group having a base-reactive substituent, and heating the reaction mixture to a temperature of between about 50 deg C. and about 150 deg C. to form a polymer. Removing any portion of the polymer results in formation of nanoscopic pores as polymer chains are decomposed, leaving pores in the polymer matrix.

Abstract: Silica-based organogels, including aerogels, incorporating hexahydrotriazine and/or hemiaminal species are described. These organo-silica gel materials can have applications as insulating materials. In a particular example, an aerogel includes silica groups and a hexahydrotriazine moiety with at least one nitrogen atom that is covalently linked to a silica group. Methods of making such silica-based organogels are also described.

Abstract: Materials which react with (“scavenge”) sulfur compounds, such as hydrogen sulfide and mercaptans, are useful for limiting sulfur-induced corrosion. Surface-modified particles incorporating a hexahydrotriazine moiety are disclosed and used as sulfur scavengers. These surface-modified particles are used a filter media in fixed filter systems and as additives to fluids including sulfur compounds. The hexahydrotriazine moiety can react with sulfur compounds in such a manner as to bind sulfur atoms to the surface-modified particles, thus allowing removal of the sulfur atoms from fluids such as crude oil, natural gas, hydrocarbon combustion exhaust gases, sulfur polluted air and water. The surface-modified particles may, in general, be sized to allow separation of the particles from the process fluid by sedimentation, size-exclusion filtration or the like.

Abstract: Embodiments of the invention are directed to a macromolecular chemotherapeutic. A non-limiting example of the macromolecular chemotherapeutic includes a block copolymer. The block copolymer can include a water-soluble block, a cationic block, and a linker, wherein the linker is connected to the water-soluble bock and the charged block.

Abstract: The present disclosure relates to polythioaminals with applications as carriers or delivery vehicles for therapeutic agents or other small molecule cargo. Polythioaminal block copolymer coupled to a therapeutic agent is a polymer-therapeutic conjugate that exhibits higher stability and longer life time in aqueous environments. The polythioaminal block copolymer coupled to a therapeutic agent can be synthesized by reacting hexahydrotriazines with a hydrophobic block precursor, a hydrophilic block precursor, a particle stabilizing segment precursor, and a cargo, such as a therapeutic agent, in a one pot synthesis. The ease of synthesizing the resulting polythioaminal block copolymer coupled to the therapeutic agent while offering the extended stability and polymer life time in aqueous environments make the polythioaminal block copolymer particularly attractive for therapeutic carriers.

Abstract: Embodiments of the disclosure generally provide compositions and methods related to oligomeric and polymeric urethane materials that contain hydrolyzable polythioaminal groups for use in biomedical applications.

Abstract: In some embodiments, a product, such as a thermoset, has a polyhexahydrotriazine and a self-polymerized cross-linkable polymer. In some embodiments, a product is the reaction product of a diamine, an aldehyde, and a compound having an ?,?-unsaturated electron withdrawing moiety.

Abstract: Silica-based organogels, including aerogels, incorporating hexahydrotriazine and/or hemiaminal species are described. These organo-silica gel materials can have applications as insulating materials. In a particular example, an aerogel includes silica groups and a hexahydrotriazine moiety with at least one nitrogen atom that is covalently linked to a silica group. Methods of making such silica-based organogels are also described.

Abstract: A block copolymer includes a water-soluble block that is bonded to one or more hydrophobic polycarbonate blocks that include pendant fluoroaryl substituents.

Abstract: Methods, compounds, and compositions described herein generally relate to polyalkylamines and syntheses thereof. In some embodiments, a chemical compound has the formula: Each instance of R is independently selected from the group consisting of aryl, alkyl, and polyether. Each instance of R? is independently selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, polyether, and alcohol. Each instance of Q and Z is independently a covalent bond or selected from the group consisting of alkyl and aralkyl.

Abstract: A composition, comprising a poly(methylene lactide) polymer covalently linked to a hexahydrotriazine unit or a hemiaminal unit, and methods of making such a composition, are described herein. In one embodiment, the poly(methylene lactide) polymer comprises a plurality of poly(methylene lactide) chains, and at least a portion of the poly(methylene lactide) chains are cross-linked by one or more of the hexahydrotriazine units, the hemiaminal units, or a combination thereof.

Abstract: In some embodiments, a product, such as a thermoset, has a polyhexahydrotriazine and a self-polymerized cross-linkable polymer. In some embodiments, a product is the reaction product of a diamine, an aldehyde, and a compound having an ?,?-unsaturated electron withdrawing moiety.

Abstract: Materials and methods for preparing a modified poly(hexahydrotriazines) (PHTs) polymers and modified polyhemiaminals (PHAs) are provided. A monomer precursor, a photochromic precursor, and a formaldehyde material may be combined to form a photochromic polymer. The photochromic polymer may comprise hexahydrotriazine, hemiaminal, polyhexahydrotriazine, polyhemiaminal, or a combination thereof.

Abstract: The disclosure describes new compositions and methods related to polyaminals and related polymers. The compositions are useful as therapeutic/drug conjugates, self-healing materials, reversible crosslinking materials, degradable hydrogels, protective coatings, and as metal scavenging agents. New atom efficient synthetic schemes are disclosed, which yield previously unobtainable high molecular weight polyaminals.

Abstract: Silica-based organogels, including aerogels, incorporating hexahydrotriazine and/or hemiaminal species are described. These organo-silica gel materials can have applications as insulating materials. In a particular example, an aerogel includes silica groups and a hexahydrotriazine moiety with at least one nitrogen atom that is covalently linked to a silica group. Methods of making such silica-based organogels are also described.

Abstract: Materials and methods for preparing a modified poly(hexahydrotriazines) (PHTs) polymers and modified polyhemiaminals (PHAs) are provided. A monomer precursor, a photochromic precursor, and a formaldehyde material may be combined to form a photochromic polymer. The photochromic polymer may comprise hexahydrotriazine, hemiaminal, polyhexahydrotriazine, polyhemiaminal, or a combination thereof.