# US 4,394,466 A · Fulvene binder compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,394,466 A - Document ID: US4394466A - Status: Granted - Kind: A - Application number: 06/320,026 - Filed: 1981-11-10 - Granted: 1983-07-19 - Earliest claimed: 1980-08-04 - Assignees: Ashland Oil, Inc. - Inventors: Bruce A. Gruber; Heimo J. Langer; William R. Dunnavant - Web page: https://patentgrep.com/patent/US4394466A ## CPC - B22C 1/2206: {obtained by reactions only involving carbon-to-carbon unsaturated bonds} - B22C 1/2233: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds} - B22C: FOUNDRY MOULDING (moulding refractory materials in general B28B) ## Abstract A binder composition which contains certain fulvenes and/or prepolymers thereof, and a metal salt catalyst. ## Claims ### Claim 1 A molding composition which comprises a major amount of aggregate and an effective bonding amount up to about 40% by weight of the aggregate of a composition capable of curing in the presence of oxygen containing a fulvene of the formula: ##STR6## wherein each R.sub.1 and R.sub.2 individually is hydrogen or a hydrocarbon containing 1 to 10 carbon atoms, or a hydrocarbon containing one or more oxygen bridges in the chain; or a furyl group; or are interconnected to form a cyclic group, each R.sub.3 and R.sub.6 individually is hydrogen or methyl, each R.sub.4 and R.sub.5 is hydrogen or methyl or ##STR7## provided that a maximum of only one such R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is methyl and provided that a maximum of any one such R.sub.4 and R.sub.5 is ##STR8## or prepolymer thereof or mixtures thereof; and a catalytic amount of a metal salt of a carboxylic acid catalyst wherein the metal constituent of said salt of a carboxylic acid is capable of existing in at least two valence states. ### Claim 2 (depends on 1) The molding composition of claim 1 which is a foundry composition containing up to about 10% by weight of the aggregate of said composition capable of curing in the presence of oxygen. ### Claim 3 (depends on 1) The molding composition of claim 1 which is a foundry composition containing up to about 0.5 to about 7% by weight of the aggregate of said composition capable of curing in the presence of oxygen. ### Claim 4 (depends on 1) The composition of claim 1 wherein said fulvene is selected from the group of dimethyl fulvene, methylisobutyl fulvene, methylisopentyl fulvene, methylphenyl fulvene, cyclohexyl fulvene, methylethyl fulvene, diphenyl fulvene, furyl fulvene, diisobutyl fulvene, isophorone fulvene, methylvinyl fulvene, methyl .beta.-methoxyisobutyl fulvene, and mixtures thereof. ### Claim 5 (depends on 1) The composition of claim 1 wherein the metal constituent of said metal salt is selected from the group of Group IB metals, Group IVA metals, Group IVB metals, Group III metals, Group VB metals, Group VII metals, and Group VIII metals. ### Claim 6 (depends on 1) The composition of claim 1 wherein said metal constituent of said salt is selected from the group of cobalt, lead, vanadium, and mixtures thereof. ### Claim 7 (depends on 1) The composition of claim 1 wherein said metal salt catalyst is a cobalt catalyst. ### Claim 8 (depends on 1) The composition of claim 1 wherein said catalyst is cobalt naphthenate. ### Claim 9 (depends on 1) The composition of claim 1 wherein said catalyst is lead naphthenate. ### Claim 10 (depends on 1) The composition of claim 1 wherein said metal salt catalyst is present in an amount of about 0.2 to about 1.2% by weight of metal based upon the weight of fulvene in the composition. ### Claim 11 (depends on 1) The composition of claim 1 which further includes an ethylenically unsaturated polymerizable material and a material selected from the group of peroxide, hydroperoxide, or mixtures thereof. ### Claim 12 (depends on 11) The composition of claim 11 wherein said ethylenically unsaturated material is a polyethylenically unsaturated material. ### Claim 13 (depends on 12) The composition of claim 12 wherein said unsaturated material is an ester of an acrylate or methacrylate, or mixture thereof. ### Claim 14 (depends on 12) The composition of claim 12 wherein said unsaturated compound is selected from the group of polyethyleneglycol diacrylate, trimethylolpropane, triacrylate, hexanediol diacrylate, and ethoxylated bisphenol-A diacrylate, and mixtures thereof. ### Claim 15 (depends on 11, 12, 13, 14) The composition of claim 11, 12, 13 or 14 wherein the amount of said ethylenically unsaturated polymerizable material is up to about 50% by weight based upon the weight of the fulvene and ethylenically unsaturated compound. ### Claim 16 (depends on 11, 12, 13, 14) The composition of claim 11, 12, 13 or 14 wherein the amount of said ethylenically unsaturated polymerizable material is about 20 to about 40% by weight based upon the weight of the fulvene and ethylenically unsaturated compound. ### Claim 17 (depends on 11) The composition of claim 11 wherein the peroxide or hydroperoxide, or mixture thereof, is present in an amount of about 1 to about 15% by weight based upon the weight of the fulvene and ethylenically unsaturated material. ### Claim 18 (depends on 11) The composition of claim 11 wherein said peroxide or hydroperoxide, or mixture thereof, is present in an amount of about 3 to about 8% by weight based upon the weight of the fulvene and ethylenically unsaturated material. ### Claim 19 (depends on 11) The composition of claim 11 wherein said peroxide is methylethyl ketone peroxide.