# US 2017/0283558 A1 · Curable benzoxazine compositions with improved thermal stability > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2017/0283558 A1 - Document ID: US20170283558A1 - Status: Published application - Kind: A1 - Application number: 15/515,162 - Filed: 2015-12-08 - Published: 2017-10-05 - Earliest claimed: 2014-12-18 - Assignees: 3M Innovative Properties Company - Applicants: 3M Innovative Properties Company - Inventors: Ilya Gorodisher; Gregory P. Sorenson; Mark McCormick; Katri M. Huikko; Robert J. Webb - Web page: https://patentgrep.com/patent/US20170283558A1 ## CPC - C08G 73/0233: {Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups} - C07D 265/16: with only hydrogen or carbon atoms directly attached in positions 2 and 4 - C09D 179/02: Polyamines - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) ## Abstract A curable benzoxazine composition is described wherein the benzoxazine is derived from an aryl amine having a b.p.>200° C. The curable compositions are more thermally stable and have reduced weight loss and by-products upon cure. ## Claims ### Claim 1 A curable composition comprising a curable benzoxazine of the formula: where each R1 is an alkyl or H; each R2 is an H, an alkyl, an aryl or a benzoxazine group; y is 1 to 4 Raryl is derived from an aryl amine having a boiling point greater than 200° C.; N-Bz represents a nitrogen-linked benzoxazine group, and z is 0 to 3; and a curative selected from the group of a thiol compounds, amine compounds, and a combination thereof. ### Claim 2 (depends on 1) The curable composition of claim 1 wherein the benzoxazine is derived from bisphenol-A. ### Claim 3 (depends on 1) The curable composition of claim 1 wherein Raryl is derived from an aryl amine having a boiling point greater than 210° C. ### Claim 4 (depends on 1) The curable composition of claim 1 wherein Raryl is derived from an aryl diamine and z is 1. ### Claim 5 (depends on 1) The curable composition of claim 1 wherein Raryl is selected from phenyl, napthyl, anthracenyl and biphenyl, each optionally substituted with one or more alkyl or aryl groups, and has a b.p.>200° C. ### Claim 6 (depends on 1) The curable composition of claim 1, wherein z is 0 or 1. ### Claim 7 (depends on 1) The curable composition of claim 1 derived from a phenol having a b.p.>200° C. ### Claim 8 (depends on 1) The curable composition of claim 1 further comprising a polyfunctional curative. ### Claim 9 (depends on 1) The curable composition of claim 1 further comprising a toughening agent. ### Claim 10 (depends on 9) The curable composition of claim 9, wherein said toughening agent is present at between about 3% and 35% by weight relative to the benzoxazine. ### Claim 11 (depends on 1) The curable composition of claim 1, further comprising a co-catalyst. ### Claim 12 (depends on 11) The curable composition of claim 11 wherein the co-catalyst is an acid catalyst. ### Claim 13 (depends on 12) The curable composition of claim 12 wherein the acid catalyst is a blocked acid catalyst. ### Claim 14 (depends on 13) The curable composition of claim 13 wherein the blocked acid catalyst is a tosylate. ### Claim 15 (depends on 1) The curable composition of claim 1 wherein the thiol curative is a polythiol. ### Claim 16 (depends on 1) The curable composition of claim 1 wherein the amine curative is a polyamine. ### Claim 17 (depends on 1) The curable composition of claim 1 wherein the curative is of the formula: R30—(ZH)p wherein, R30 is a (hetero)hydrocarbyl group; each Z is independently —S— or —NR31, where R31 is H or a hydrocarbyl group, including aryl and alkyl; and p is 1 to 6. ### Claim 18 (depends on 17) The curable composition of claim 17 wherein p is 2 to 6. ### Claim 19 (depends on 17) The curable composition of claim 17 wherein the molar amounts ratio of benzoxazine groups to the “Z” groups, is 3:2 to 100:1. ### Claim 20 (depends on 17) The curable composition of claim 17 wherein the molar amounts ratio of benzoxazine groups to the “Z” groups, is 4:1 to 50:1. ### Claim 21 (depends on 1) The curable composition of claim 1 wherein the curative is present in an amount of at least 5 wt. %, to 60% of the benzoxazine equivalent ### Claim 22 (depends on 1) The curable composition of claim 1 further comprising an epoxy resin. ### Claim 23 (depends on 22) The curable composition of claim 22 wherein the epoxy resin is used in amounts of 3 to 35 wt. % relative to the benzoxazine.