# US 9,751,974 B2 · Aminoanthracene—epoxy nanocomposite containing free anthracene > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,751,974 B2 - Document ID: US9751974B2 - Status: Granted - Kind: B2 - Application number: 14/478,917 - Filed: 2014-09-05 - Published: 2015-03-12 - Granted: 2017-09-05 - Earliest claimed: 2013-09-06 - Assignees: Honeywell Federal Manufacturing & Technologies, LLC - Applicants: Honeywell Federal Manufacturing & Technologies, LLC - Inventors: Daniel Bowen; Somnath Sarkar - Web page: https://patentgrep.com/patent/US9751974B2 ## CPC - C08G 59/5033: {aromatic} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS ## Abstract Polymeric nanocomposite materials are provided comprising polycyclic aromatic hydrocarbon compounds. During polymer synthesis, polycyclic aromatic hydrocarbon groups are directly incorporated into the polymer network. Free polycyclic aromatic hydrocarbon compounds are also dispersed within the polymer matrix. The resulting nanocomposite materials exhibit improvements in the thermal, rheological, and physical properties, including reinforcement, of the polymer material as compared to the unmodified polymer. ## Claims ### Claim 1 A nanocomposite material comprising: a polymer matrix comprising a polymeric material having one or more functionalized polycyclic aromatic hydrocarbon moieties, wherein said one or more functionalized polycyclic aromatic hydrocarbon moieties comprise fused aromatic rings; and from about 0.05 to about 25% by weight, based upon the weight of said nanocomposite material, of one or more functionalized or non-functionalized free polycyclic aromatic hydrocarbon compounds dispersed within said polymer matrix, wherein said one or more free polycyclic aromatic hydrocarbon compounds comprise fused aromatic rings. ### Claim 2 (depends on 1) The nanocomposite material according to claim 1, wherein said one or more polycyclic aromatic hydrocarbon moieties comprise from about 0.05 to about 25% by weight of said nanocomposite material. ### Claim 3 (depends on 1) The nanocomposite material according to claim 1, wherein said functionalized polycyclic aromatic hydrocarbon moiety comprises an aminoanthracene derivative. ### Claim 4 (depends on 1) The nanocomposite material according to claim 1, wherein said polymeric material comprises an epoxy resin polymer. ### Claim 5 (depends on 4) The nanocomposite material according to claim 4, wherein said one or more functionalized polycyclic aromatic hydrocarbon moieties are attached to said epoxy resin polymer via nucleophilic addition to one or more epoxide moieties. ### Claim 6 (depends on 1) The nanocomposite material according to claim 1, wherein said one or more free polycyclic aromatic hydrocarbon compounds comprise a member selected from the group consisting of asphaltenes, functionalized asphaltenes, anthracene, functionalized anthracenes, naphthalene, functionalized naphthalenes, and combinations thereof. ### Claim 7 (depends on 6) The nanocomposite material according to claim 6, wherein said one or more free polycyclic aromatic hydrocarbon compounds comprises an aminoanthracene compound. ### Claim 8 (depends on 1) The nanocomposite material according to claim 1, wherein said one or more polycyclic aromatic hydrocarbon moieties are derived from said one or more polycyclic aromatic hydrocarbon compounds. ### Claim 9 (depends on 1) The nanocomposite material according to claim 1, wherein said composite material comprises a Tg value that is greater than the Tg value of said polymeric material without said polycyclic aromatic hydrocarbon moieties. ### Claim 10 (depends on 1) The nanocomposite material according to claim 1, wherein said nanocomposite material has a thermal decomposition temperature that is greater than the thermal decomposition temperature of said polymeric material without said polycyclic aromatic hydrocarbon moieties. ### Claim 11 A nanocomposite material comprising: a polymer matrix comprising an epoxy resin polymer having one or more functionalized polycyclic aromatic hydrocarbon moieties, wherein said one or more functionalized polycyclic aromatic hydrocarbon moieties comprise fused aromatic rings; and from about 0.05 to about 25% by weight, based upon the weight of said nanocomposite material, of a molecular nanofiller comprising one or more functionalized or non-functionalized free polycyclic aromatic hydrocarbon compounds dispersed within said polymer matrix, wherein said one or more free polycyclic aromatic hydrocarbon compounds comprise fused aromatic rings. ### Claim 12 (depends on 11) The nanocomposite material according to claim 11, wherein said one or more free polycyclic aromatic hydrocarbon compounds comprise a member selected from the group consisting of asphaltenes, functionalized asphaltenes, anthracene, functionalized anthracenes, naphthalene, functionalized naphthalenes, and combinations thereof. ### Claim 13 (depends on 12) The nanocomposite material according to claim 12, wherein said one or more free polycyclic aromatic hydrocarbon compounds comprises an aminoanthracene compound. ### Claim 14 (depends on 11) The nanocomposite material according to claim 11, wherein said epoxy resin polymer comprises the reaction product of an epoxy-functional monomer and an amine curing agent. ### Claim 15 (depends on 11) The nanocomposite material according to claim 11, wherein said functionalized polycyclic aromatic hydrocarbon moiety is an aminoanthracene derivative. ### Claim 16 A method of producing a nanocomposite material comprising: providing one or more resin materials capable of reacting to form a polymeric material; mixing said one or more resin materials with at least one amino-functional polycyclic aromatic hydrocarbon compound, wherein said at least one amino-functional polycyclic aromatic hydrocarbon compound comprises fused aromatic rings; reacting said at least one amino-functional polycyclic aromatic hydrocarbon compound and said one or more resin materials under conditions sufficient to form a reaction mixture comprising a polymer having amino-functional polycyclic aromatic hydrocarbon moieties derived from said at least one amino-functional polycyclic aromatic hydrocarbon compound, wherein said amino-functional polycyclic aromatic hydrocarbon moieties comprise fused aromatic rings, and wherein said reaction mixture comprises said nanocomposite material, said nanocomposite material comprising from about 0.05 to about 25% by weight, based upon the weight of said nanocomposite material, of a molecular nanofiller comprising unreacted amino-functional polycyclic aromatic hydrocarbon compound. ### Claim 17 (depends on 16) The method according to claim 16, wherein said at least one polycyclic aromatic hydrocarbon compound is dispersed in a solvent prior to being mixed with said one or more resin materials. ### Claim 18 (depends on 17) The method according to claim 17, wherein said method further comprises, following said reacting step, removing at least a portion of said solvent from said reaction mixture. ### Claim 19 (depends on 17) The method according to claim 17, wherein said reacting step comprises reacting said at least one polycyclic aromatic hydrocarbon compound and said one or more resin materials under reflux conditions. ### Claim 20 (depends on 16) The method according to claim 16, wherein said one or more resin materials comprise an epoxy resin having at least two epoxide functional groups and an aliphatic amine curing agent. ### Claim 21 A nanocomposite material comprising: a polymer matrix comprising a polymeric material having one or more polycyclic aromatic hydrocarbon moieties and said polymeric material comprises an epoxy resin polymer, wherein said one or more polycyclic aromatic hydrocarbon moieties comprise fused aromatic rings, wherein said one or more polycyclic aromatic hydrocarbon moieties are attached to said epoxy resin polymer via nucleophilic addition to one or more epoxide moieties; and from about 0.05 to about 25% by weight, based upon the weight of said nanocomposite material, of one or more functionalized or non-functionalized free polycyclic aromatic hydrocarbon compounds dispersed within said polymer matrix, wherein said one or more free polycyclic aromatic hydrocarbon compounds comprise fused aromatic rings. ### Claim 22 A nanocomposite material comprising: a polymer matrix comprising a polymeric material having one or more polycyclic aromatic hydrocarbon moieties, wherein said one or more polycyclic aromatic hydrocarbon moieties comprise fused aromatic rings; and from about 0.05 to about 25% by weight, based upon the weight of said nanocomposite material, of a free polycyclic aromatic hydrocarbon compound dispersed within said polymer matrix comprising an aminoanthracene compound. ### Claim 23 A nanocomposite material comprising: a polymer matrix comprising an epoxy resin polymer having one or more polycyclic aromatic hydrocarbon moieties, wherein said one or more polycyclic aromatic hydrocarbon moieties comprise fused aromatic rings; and from about 0.05 to about 25% by weight, based upon the weight of said nanocomposite material, of a molecular nanofiller comprising a free polycyclic aromatic hydrocarbon compound dispersed within said polymer matrix an aminoanthracene compound.