# US 11,028,204 B2 · Curable compositions comprising mono-functional acrylates > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,028,204 B2 - Document ID: US11028204B2 - Status: Granted - Kind: B2 - Application number: 15/743,345 - Filed: 2016-07-07 - Published: 2018-07-12 - Granted: 2021-06-08 - Earliest claimed: 2015-07-10 - Assignees: Arkema France - Applicants: Arkema France - Inventors: Sumeet Jain; William C. Wolf; Yuhong He; Jeffrey A. Klang - Web page: https://patentgrep.com/patent/US11028204B2 ## CPC - B05D 3/067: {Curing or cross-linking the coating} - B05D 3/068: {using ionising radiations (gamma, X, electrons)} - B05D 3/108: {Curing} - B33Y 70/00: Materials specially adapted for additive manufacturing - C08F 232/08: having condensed rings (coumarone-indene polymers C08F244/00) - C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} - C09D 4/06: {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00 - C08F 222/102: {of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate} - C08F 222/1061: {of alcohol terminated polyesters or polycarbonates, e.g. polyester (meth)acrylates} - C08F 222/1065: {of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates} - C08F 222/1067: {of alcohol terminated epoxy functional polymers, e.g. epoxy(meth)acrylates} - B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02) - B33Y: ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - 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 Curable compositions include: a) at least one (meth)acrylate monomer or oligomer and b) at least one mono-functional (meth)acrylate monomer comprising a polycyclic moiety having at least three rings that are fused or condensed. The compositions may comprise an initiator system to render the compositions as curable. The compositions may comprise both the a) and b) components in an amount from about 30% to about 70% by weight. The compositions described herein are advantageous with respect to properties such as viscosity, toughness, tensile strength and tensile elongation. Due to their advantageous properties, the compositions are viable for a wide range of applications including coatings, adhesives, sealants, inks and stereolithography. The compositions are liquid at ambient temperature and impart a high glass transition temperature, Tg, without sacrificing other properties, such as elongation. The compositions are useful in 3D printing. ## Claims ### Claim 1 A curable composition comprising: a) at least one (meth)acrylate or oligomer selected from the group consisting of monofunctional oligomeric (meth)acrylates, multifunctional oligomeric (meth)acrylates, and combinations thereof; b) at least one mono-functional (meth)acrylate monomer comprising tricyclodecane methanol monoacrylate having three rings that are fused or condensed; and wherein a) and b) are different. ### Claim 2 (depends on 1) The curable composition of claim 1, wherein the b) at least one mono-functional (meth)acrylate monomer comprises tricyclo-[5,2,1,0]-decane. ### Claim 3 (depends on 1) The curable composition of claim 1, wherein the composition further includes d) at least one (meth)acrylated monomer having a bicyclic group having at least 7 carbon atoms. ### Claim 4 (depends on 1) The curable composition of claim 1, wherein the composition is curable by techniques selected from the group consisting of radiation curable, electron beam curable, peroxide curable, heat curable or combination thereof. ### Claim 5 (depends on 1) The curable composition of claim 1, wherein the composition includes c) at least one initiator system. ### Claim 6 (depends on 1) The curable composition of claim 1, wherein the a) at least one (meth)acrylate monomer or oligomer is present in the composition from about 30% to about 70% by weight based on the total weight of the composition and the b) at least one mono-functional (meth)acrylate monomer is present in the composition from about 30% to about 70% by weight based on the total weight of the composition. ### Claim 7 (depends on 1) The curable composition of claim 1, wherein the composition has a viscosity of less than 4000 mPa·s (cP) at 25° C. ### Claim 8 (depends on 1) The curable composition of claim 1, wherein the a) at least one (meth)acrylate oligomer has an average in number-functionality of from about 1.1 to about 1.9 (meth)acrylates. ### Claim 9 (depends on 1) The curable composition of claim 1, wherein the composition further comprises a compound selected from the group consisting of mono- and/or multifunctional monomers, wetting agents, matting agents, colorants (such as dyes or pigments), adhesion promoters, fillers, rheology modifiers, thixotropic agents, plasticizers, UV absorbers, UV stabilizing agents, dispersants, antioxidants, antistatic agents, lubricants, opacifying agents, anti-foam agents or rheology agents and combinations thereof. ### Claim 10 (depends on 1) The curable composition of claim 1, wherein the composition is a curable coating, a curable adhesive, a curable sealant, a curable ink or a curable stereolithography or a curable 3D-impression composition. ### Claim 11 (depends on 1) A cured composition resulting from curing the curable composition of claim 1. ### Claim 12 (depends on 11) A cured article comprising the cured composition of claim 11. ### Claim 13 (depends on 12) The cured article of claim 12, wherein the article is selected from a coating, an adhesive, a sealant, an ink or a three-dimensional (3D) article made by stereolithography or a 3D-article made by 3D-impression. ### Claim 14 (depends on 1) A 3D-impression resulting from a curable composition of claim 1. ### Claim 15 (depends on 1) A method of coating a substrate comprising the steps of: applying to said substrate the curable composition of claim 1; and curing the resulting substrate by exposure to one of visible radiation, UV radiation, LED radiation, electron-beam radiation or chemicals. ### Claim 16 (depends on 15) The method of claim 15, wherein the applying comprises applying to a substrate by spraying, by knife coating, by roller coating, by casting, by drum coating, by dipping and combinations thereof. ### Claim 17 (depends on 1) A method for preparing a coating, an adhesive, a sealant, an ink, a stereo-lithography, a three-dimensional article or a three-dimensional impression, a digital printing and an additive comprising curing the curable composition of claim 1. ### Claim 18 (depends on 1) A method of preparing a three-dimensional for bottom-up comprising curing the curable composition of claim 1. ### Claim 19 (depends on 1) The curable composition of claim 1 further comprising at least one compound selected from the group consisting of 3,3,5-trimethyl cyclohexanol acrylate, tert-butyl cyclohexanol acrylate, isobornyl acrylate, tricyclodecane dimethanol diacrylate, 2-phenoxyethyl acrylate, cyclic trimethylolpropane formal acrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, triallyl isocyanurate triacrylate, 2-(2-ethoxyethoxy) ethyl acrylate, isodecyl acrylate, poly(ethylene glycol) diacrylates and combinations thereof. ### Claim 20 (depends on 1) The curable composition of claim 1, wherein the monofunctional oligomeric (meth)acrylates, multifunctional oligomeric (meth)acrylates, and combinations thereof are selected from the group consisting of urethane acrylate oligomers, epoxy acrylate oligomers, polyester acrylate oligomers, and combinations thereof. ### Claim 21 (depends on 1) The curable composition of claim 1, wherein the a) at least one (meth)acrylate oligomer is present in the composition from about 10% to about 90% by weight based on the total weight of the composition and the b) at least one mono-functional (meth)acrylate monomer is present in the composition from about 10% to about 90% by weight based on the total weight of the composition. ### Claim 22 (depends on 1) The curable composition of claim 1 further comprising tricyclodecane dimethanol diacrylate.