Abstract: A porous material includes a resin material based on a trifunctional ethynyl monomer. Pores in the porous material can be of various sizes including nanoscale sizes. The porous material may be used in a variety of applications, such as those requiring materials with a high strength-to-weight ratio. The porous material can include a filler material dispersed therein. The filler material can be, for example, a particle, a fiber, a fabric, or the like. In some examples, the filler material can be a carbon fiber or a carbon nanotube. A method of making a porous material includes forming a resin including a trifunctional ethynyl monomer component and a polythioaminal component. The resin can be heated to promote segregation of the components into different phases with predominately one or the other component in each phase. Processing of the resin after phase segregation to decompose the polythioaminal component can form pores in the resin.

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: Compounds include boronate ester polythioaminals with substituents that include hydrogen, fluorine or substituted or unsubstituted alkyls. The boronate ester polythioaminals have number average molecular weight or weight average molecular weight between about 2,000 to about 160,000.

Abstract: A porous material includes a polyhexahydrotriazine material. Pores in the porous material can be of various sizes including nanoscale sizes. The porous material may be used in a variety of applications, such as those requiring materials with a high strength-to-weight ratio. The porous material can include a filler material dispersed therein. The filler material can be, for example, a particle, a fiber, a fabric, or the like. In some examples, the filler material can be a carbon fiber or a carbon nanotube. A method of making a porous material includes forming a resin including a polyhemiaminal or polyhexahydrotriazine component and a polythioaminal component. The resin can be heated to promote segregation of the components into different phases with predominately one or the other component in each phase. Processing of the resin after phase segregation to decompose the polythioaminal component can form pores in the resin.

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: Method and apparatus for controlling metals in a liquid are described. The liquid is contacted with a hexahydrotriazine and/or a hemiaminal material, and metal is adsorbed from the liquid onto the material. The hexahydrotriazine and/or hemiaminal material may be made from a diamine and an aldehyde.

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: 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 degC and about 150 degC 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: Methods and materials for patterning a substrate are disclosed herein. A poly(thioaminal) material may be utilized as a thermal resist material for patterning substrates in a thermal scanning probe lithography process. The poly(thioaminal) material may be functionalized with an electron withdrawing group and various monomers may be volatilized upon exposure to a thermal scanning probe.

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: 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: A polymeric material comprising a polyethylenimine-based material including the following moiety: attached thereto, wherein R1 is a group including at least one carbon atom and n is from 2 to 4 is disclosed. A method for preparing a polyethylenimine-based material is disclosed. A gene therapy method using a polymeric material including polyethylenimine-based material is also disclosed.

Abstract: Methods, compounds, and compositions described herein generally relate to hemiaminal organogel networks (HDCNs) and methods of forming HDCNs. In some embodiments, a hemiaminal organogel has a plurality of first polymers, each having a first end and a second end, a plurality of second polymers, each having a first end and a second end, and a plurality of trivalent aminal-hemiaminal linkages. The first end of each polymer of the plurality of first polymers may be covalently bonded to a first trivalent aminal-hemiaminal linkage. The second end of each polymer of the plurality of first polymers may be covalently bonded to a second trivalent aminal-hemiaminal linkage. The first end of each polymer of the plurality of second polymers may be covalently bonded to one of the plurality of trivalent aminal-hemiaminal linkages. The second end of each polymer of the plurality of second polymers may be non-covalently bonded.

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

Abstract: Compounds include boronate ester polythioaminals with substituents that include hydrogen, fluorine or substituted or unsubstituted alkyls. The boronate ester polythioaminals have number average molecular weight or weight average molecular weight between about 2,000 to about 160,000.

Abstract: Thioaminal polymers are made from hexahydrotriazine precursors and dithiol precursors. The precursors are blended together and subjected to mild heating to make the polymers. An amine scavenger is used to remove amine byproducts from the reaction, thus promoting polymer growth to high molecular weight. The polymers have the general structure wherein each R1 is independently an organic or hetero-organic group, a plurality of R2 groups are substituents having molecular weight greater than about 120 Daltons, and n is an integer greater than or equal to 1. The polymers may be functionalized by adding a thiol-reactive group to either end or both ends.

Abstract: Methods and materials for preparing a covalent 3D nano-object are provided. A diamine or triamine monomer and a monoamine terminated precursor may be reacted to form a star polymer material. A cross-linking polymerization process may in a nanogel core with the monoamine terminated precursor covalently linked to the nanogel core. The covalent 3D nano-object may comprise HT, PHT, HA, and/or PHA materials.

Abstract: Materials include compounds such as polyboroaminals of the formula, and salts or adducts thereof: Each instance of R1, R2, R3, and R4 is independently —H or substituted or unsubstituted alkyl, cycloalkyl, alkenyl, alkoxyl, aryl, heterocyclyl or R3 and R4 combine to form a 5-membered cycloalkyl or heterocyclyl or 6-membered aryl, cycloalkyl or heterocyclyl. Each instance of R5 is independently —H, halo, or alkyl. n is a positive integer and the number average molecular weight or weight average molecular weight of the compound of formula (I) is between about 2,000 to about 80,000.

Abstract: A polymer is described herein that includes a plurality of N-J-N or N—C—S repeating units, wherein each J is independently a carbon atom, an alkyl group, or an aryl group; a plurality of hydrophilic groups bonded with the repeating units; and a plurality of hydrophobic groups bonded with the hydrophilic groups and the repeating units. Such polymers may be made into hydrogels by exposure to water, and the hydrogels may be used as delivery vehicles for various payloads.

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.