# US 4,394,497 A · Solid materials prepared from epoxy resins and phenolic hydroxyl-containing materials > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,394,497 A - Document ID: US4394497A - Status: Granted - Kind: A - Application number: 06/362,799 - Filed: 1982-03-29 - Granted: 1983-07-19 - Earliest claimed: 1982-03-29 - Assignees: The Dow Chemical Company - Inventors: Donald L. Nelson; Bryan A. Naderhoff - Web page: https://patentgrep.com/patent/US4394497A ## CPC - C08G 59/066: {with chain extension or advancing agents} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS ## Abstract Solid compositions are prepared by reacting (A) one or more materials containing an average of more than one 1,2-epoxy groups with (B) one or more materials containing an average of more than one phenolic hydroxy groups wherein at least one of (A) or (B) contains with respect to (B) or has been prepared from with respect to (A) a reaction product of (1) at least one aromatic compound having at least one aromatic ring, at least one aromatic hydroxyl group and which aromatic ring contains at least one ortho or para position which is capable of being alkylated and (2) at least one aliphatic or cycloaliphatic C.sub.4 -C.sub.6 unsaturated hydrocarbon or a dimer, codimer, oligomer or cooligomer thereof. ## Claims ### Claim 1 Solid compositions resulting from reacting, in the presence of an effective quantity of a suitable catalyst, (I) at least one material having an average of more than one 1,2-epoxy group per molecule with (II) at least one material having an average of more than one phenolic hydroxyl group per molecule; wherein at least one of (I) or (II) contains with respect to (II) or has been prepared from with respect to (I) a reaction product of (A) at least one aromatic compound containing (1) at least one aromatic ring, (2) at least one aromatic hydroxyl group and (3) which aromatic ring has at least one ortho or para position capable of being alkylated, and (B) at least one unsaturated aliphatic or cycloaliphahtic hydrocarbon containing 4 to 6 carbon atoms or one or more dimers or oligomers thereof, or mixtures thereof. ### Claim 2 (depends on 1) A composition of claim 1 wherein component (I) contains an epoxy resin composition resulting from the dehydrohalogenation of the reaction product of (A) an epoxy alkyl halide; with (B) an acid catalyzed product resulting from reacting (1) at least one aromatic hydroxyl-containing compound having at least one aromatic ring and at least one ortho or para position with respect to a hydroxyl group available for ring alkylation; with (2) at least one unsaturated hydrocarbon selected from (a) unsaturated hydrocarbons having from 4 to 6 carbon atoms; or (b) dimers, codimers, oligomers or cooligimers of unsaturated hydrocarbons, which hydrocarbons have 4 to 6 carbon atoms; and wherein the components (B-1) and (B-2) are employed in quantities which provide a mole ratio of (B-1) to (B-2) of from about 1.8:1 to about 30:1, and components (A) and (B) are employed in quantities which provide an epoxy group to phenolic hydroxyl group ratio of from about 1.5:1 to about 20:1. ### Claim 3 (depends on 2) A composition of claim 2 wherein the mole ratio of component (B-1) to component (B-2) is from about 1.8:1 to about 20:1 and the epoxy group to phenolic hydroxyl group ratio provided by components (A) and (B) is from about 3:1 to about 5:1. ### Claim 4 (depends on 3) A composition of claim 3 wherein component (A) is epichlorohydrin. ### Claim 5 (depends on 1, 2, 3, 4) A composition of claims 1, 2, 3 or 4 wherein component (II) contains a material which is an acid catalyzed product resulting from reacting (A) at least one aromatic compound containing at least one aromatic hydroxyl-group and at least one aromatic ring and at least one ortho or para position relative to a hydroxyl group available for ring alkylation; with (B) at least one unsaturated hydrocarbon selected from (1) unsaturated hydrocarbons having from 4 to 6 carbon atoms; or (2) dimers, codimers, oligomers or cooligomers of unsaturated hydrocarbons, which hydrocarbons have from 4 to 6 carbon atoms; and wherein components (A) and (B) are employed in quantities which provide a mole ratio of component (A) to component (B) of from about 1.8:1 to about 30:1 and wherein said catalyst is employed in quantities of from about 0.01% to about 5% by weight of the quantity of component (A). ### Claim 6 (depends on 5) A composition of claim 5 wherein components (A) and (B) are employed in quantities which provides a mole ratio of (A) to (B) of from about 1.8:1 to about 20:1 and said catalyst employed in a quantity from about 0.3% to about 1% by weight of component (A). ### Claim 7 (depends on 2, 3, 4) A composition of claims 2, 3 or 4 wherein component (B-1) is phenol and component (B-2) is a composition comprising (1) from about 70% to about 94% by weight of dicyclopentadiene; (2) from about 6 to about 30 percent by weight of C.sub.10 dimers; (3) from about zero to about 7 percent by weight of oligomers of C.sub.4 -C.sub.6 unsaturated hydrocarbon; and (4) the balance, if any, to provide 100% by weight of C.sub.4 -C.sub.6 alkanes, alkenes and dienes. ### Claim 8 (depends on 5) A composition of claim 5 wherein component (A) is phenol and component (B) is a composition comprising (1) from about 70% to about 94% by weight of dicyclopentadiene; (2) from about 6 to about 30 percent by weight of C.sub.10 dimers; (3) from about zero to about 7 percent by weight of oligomers of C.sub.4 -C.sub.6 unsaturated hydrocarbon; and (4) the balance, if any, to provide 100% by weight of C.sub.4 -C.sub.6 alkanes, alkenes and dienes. ### Claim 9 (depends on 6) A composition of claim 6 wherein component (A) is phenol and component (B) is a composition comprising (1) from about 70% to about 94% by weight of dicyclopentadiene; (2) from about 6 to about 30 percent by weight of C.sub.10 dimers; (3) from about zero to about 7 percent by weight of oligomers of C.sub.4 -C.sub.6 unsaturated hydrocarbon; and (4) the balance, if any, to provide 100% by weight of C.sub.4 -C.sub.6 alkanes, alkenes and dienes.