# US 2016/0243274 A1 · Hardenable Multi-Part Acrylic Composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2016/0243274 A1 - Document ID: US20160243274A1 - Status: Published application - Kind: A1 - Application number: 15/026,111 - Filed: 2014-09-30 - Published: 2016-08-25 - Earliest claimed: 2013-09-30 - Assignees: Lucite International Speciality Polymers and Resins Limited - Applicants: Lucite International Speciality Polymers & Resins Limited - Inventors: Michael Stephen Chisholm; Sera Saheb Abed-Ali - Web page: https://patentgrep.com/patent/US20160243274A1 ## CPC - A61L 24/06: obtained by reactions only involving carbon-to-carbon unsaturated bonds {(A61L24/043, A61L24/046 take precedence)} - A61K 6/889: Polycarboxylate cements; Glass ionomer cements - A61L 24/001: {Use of materials characterised by their function or physical properties} - A61L 27/16: obtained by reactions only involving carbon-to-carbon unsaturated bonds - A61L 27/50: Materials characterised by their function or physical properties {, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials} - C08F 265/06: Polymerisation of acrylate or methacrylate esters on to polymers thereof - C08F 292/00: Macromolecular compounds obtained by polymerising monomers on to inorganic materials - C08K 3/30: Sulfur-, selenium- or tellurium-containing compounds - C08L 33/12: Homopolymers or copolymers of methyl methacrylate - C08L 33/14: of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen - A61L 2430/02: for reconstruction of bones; weight-bearing implants - C08K 2003/3045: {Sulfates} - A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K) - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract The invention relates to a hardenable multi-part liquid acrylic composition. The composition comprises a storage stable liquid first part, a storage stable liquid second part and optionally, a third or further liquid parts. The parts are operable to form a cement which hardens to a solid upon mixing of the parts together. The composition comprises an acrylic monomer component, an initiator component,acrylic polymer particles and a radiopacifying filler. The initiator component is present in an amount of effective topolymerize the acrylic monomer component upon being mixed and/or activated therewith. At least some of the radiopacifying filler is encapsulated within and/or adsorbed on the acrylic polymer particles in a liquid part. The invention extends to an at least twin barreled syringe or caulking gun accommodating the multi-part composition, a method of producing the multi-part composition, a composition for use as bone cement composition or in dental repairs, a liquid composition comprising a first sub-population of emulsion or non-emulsion polymerized acrylic polymer particles and radiopacifying filler encapsulated and/or adsorbed in the first sub-population of acrylic polymer particles and bone cement compositions or dental compositions. ## Claims ### Claim 1 A hardenable multi-part acrylic composition comprising a storage stable liquid first part, a storage stable liquid second part, and optionally, a third or further liquid parts adapted to form a cement which hardens to a solid upon mixing of the parts together, wherein: the composition comprises an acrylic monomer component, an initiator component, acrylic polymer particles and a radiopacifying filler, the initiator component is present in an amount effective to polymerize the acrylic monomer component upon mixing the pars together such that at least some of the radiopacifying filler is encapsulated within and/or adsorbed on the acrylic polymer particles in a liquid part. ### Claim 2 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein the acrylic polymer particles comprise two or more sub-populations of acrylic polymer particles. ### Claim 3 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein the acrylic polymer particles with encapsulated and/or adsorbed radiopacifying filler are present in a liquid carrier in the liquid first part and/or liquid second part. ### Claim 4 (depends on 3) The hardenable multi-part acrylic composition according to claim 3, wherein the liquid carrier is water or other liquid, the other liquid comprising a monomer, organic solvent, plasticizer, liquid polymer, diluent, or acrylic monomer. ### Claim 5 (depends on 4) The hardenable multi-part acrylic composition according to claim 4, wherein the liquid carrier is water. ### Claim 6 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein at least some of the radiopacifying filler is encapsulated within and/or adsorbed on the acrylic polymer particles in suspension in a liquid part. ### Claim 7 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein between 20 and 100% w/w of the radiopacifying filler in the composition is encapsulated within and/or adsorbed on acrylic polymer particles. ### Claim 8 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein an overall amount of radiopacifying filler in the hardenable multi-part composition is between 1 and 50% w/w. ### Claim 9 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein one or more sub-population(s) of acrylic polymer particles in the composition have a lower average particle size than an average particle size of sub-population(s) having encapsulated and/or adsorbed radiopacifying filler. ### Claim 10 (depends on 9) The hardenable multi-part acrylic composition according to claim 9, wherein the average particle size of the lower average particle size sub-population is 0.01-30 μm. ### Claim 11 (depends on 9) The hardenable multi-part acrylic composition according to claim 9, wherein lower average particle size sub-populations are kept apart from the monomer so that the lower average particle size sub-population(s) preferentially dissolve in the monomer after mixing thereby preventing or reducing dissolution of the sub-population(s) and having encapsulated and/or adsorbed radiopacifying filler. ### Claim 12 (canceled) ### Claim 13 (depends on 10) The hardenable multi-part acrylic composition according to claim 10, wherein when bead particles are present, the mean particle size of the lower average particle size sub-population(s) ranges from 1 μm to 30 μm. ### Claim 14 (depends on 13) The hardenable multi-part acrylic composition according to claim 13, wherein the lower average particle size sub-population(s) are emulsion particles. ### Claim 15 (depends on 9) The hardenable multi-part acrylic composition according to claim 9, wherein the average particle size of the sub-population(s) having encapsulated and/or adsorbed radiopacifying filler is in the range from 10 to 1000 μm. ### Claim 16 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein the radiopacifying filler is encapsulated within and/or adsorbed on polymer beads or in two or more bead sub-populations. ### Claim 17 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein substantially all the acrylic monomer component in the composition is present in the liquid second part. ### Claim 18 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein substantially all of the acrylic monomer component and the initiator component are located in separate parts of the multi-part composition so that the part containing the monomer component is storage stable to polymerization. ### Claim 19 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein the radiopacifying filler is only encapsulated within and/or adsorbed on acrylic polymer beads. ### Claim 20 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein the radiopacifying filler is encapsulated and/or adsorbed in only the first part of the composition. ### Claim 21 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein the radiopacifying filler is only encapsulated and/or adsorbed in acrylic polymer beads. ### Claim 22 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein at least 50% w/w of the total encapsulated and/or adsorbed radiopacifying filler in the composition is present in acrylic polymer beads. ### Claim 23 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein radiopacifying fillers comprise at least one of zirconium dioxide, strontium carbonate, powdered tantalum, powdered tungsten, barium sulphate and mixtures thereof. ### Claim 24 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein the radiopacifying fillers are zirconium dioxide, barium sulphate, and mixtures thereof. ### Claim 25 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein the liquid first part comprises acrylic polymer particles present as polymer beads and having encapsulated and/or adsorbed radiopacifying filler, the liquid second part comprises the monomer component, the composition comprises emulsion polymerized acrylic polymer particles and the emulsion polymerized acrylic polymer particles are dispersed in a liquid carrier. ### Claim 26 (depends on 26) The hardenable multi-part acrylic composition according to claim 26, wherein the liquid part containing the acrylic polymer particles and encapsulated and/or adsorbed radiopacifying filler further contains the emulsion polymerized acrylic polymer particles, the emulsion polymerized particles in the liquid carrier are in the form of an acrylic polymer emulsion dispersion and the liquid carrier for the acrylic polymer particles, encapsulated and/or adsorbed radiopacifying filler and emulsion polymerized acrylic polymer particles is water. ### Claim 27 (canceled) ### Claim 28 (depends on 26) The hardenable multi-part acrylic composition according to claim 26, wherein the liquid carrier forms between 5-90% w/w of the liquid part in which acrylic polymer particle encapsulated and/or adsorbed radiopacifying filler is present. ### Claim 29 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein the amount of monomer in the hardenable composition ranges from 10% w/w to 70 % w/w. ### Claim 30 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein at least 90% w/w of the total radiopacifying filler in the composition is present in the liquid first part. ### Claim 31 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein substantially all of the acrylic monomer component and the radiopacifying filler are located in separate parts of the composition so that the radiopacifying filler is not substantially present in a polymer matrix of the final hardened material. ### Claim 32 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein at least 90% w/w of the total acrylic polymer particles with encapsulated and/or adsorbed radiopacifying filler in the composition are present in the liquid first part. ### Claim 33 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein substantially all of the acrylic monomer component and the acrylic polymer particles with encapsulated and/or adsorbed radiopacifying filler are located in separate parts of the composition so that encapsulated and or adsorbed radiopacifying filler is not released into the monomer component prior to mixing and therefore released radiopacifying filler presence in the polymer matrix of the final hardened material is reduced. ### Claim 34 (depends on 26) The hardenable multi-part acrylic composition according to claim 26, wherein at least 90% w/w of the total emulsion polymerized acrylic particles present in the composition is present in the liquid first part. ### Claim 35 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein a sub-population in the liquid first part includes emulsion polymerized particles and water as a liquid carrier. ### Claim 36 (depends on 1) The hardenable multi-part acrylic composition according to claim 1, wherein the multi-part acrylic composition is a bone cement or dental composition. ### Claim 37 A liquid composition comprising a first sub-population of emulsion or non-emulsion polymerized acrylic polymer particles, optionally at least one further sub-population of emulsion or non-emulsion polymerized acrylic polymer particles, a polymerization initiator in the liquid composition at a level sufficient to cause the liquid composition to harden upon contact with a reactive monomer liquid, and a radiopacifying filler encapsulated and/or adsorbed in the first sub-population of acrylic polymer particles. ### Claim at position 38 38-41. (canceled)