# US 11,898,046 B2 · Photopolymerization initiator and producing method thereof, polymerizable composition, ink jet recording method, and acylphosphine oxide compound > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,898,046 B2 - Document ID: US11898046B2 - Status: Granted - Kind: B2 - Application number: 17/159,410 - Filed: 2021-01-27 - Published: 2021-05-20 - Granted: 2024-02-13 - Earliest claimed: 2015-11-20 - Assignees: FUJIFILM Corporation - Applicants: Fujifilm Corporation - Inventors: Hiroaki Tsuyama; Kazuhiro Yokoi; Kouki Nakamura; Kenjiro Araki - Web page: https://patentgrep.com/patent/US11898046B2 ## CPC - C09D 11/38: characterised by non-macromolecular additives other than solvents, pigments or dyes - B41M 5/00: Duplicating or marking methods; Sheet materials for use therein (by using light-sensitive materials G03; electrography, magnetography G03G {; repeatedly usable boards or tablets for writing or drawing B43L1/00}) - B41M 7/0081: {using electromagnetic radiation or waves, e.g. ultraviolet radiation, electron beams} - C07F 9/53: Organo-phosphine oxides; Organo-phosphine thioxides - C07F 9/5337: {Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)} - C08F 2/50: with sensitising agents - 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) - B41M: PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING, (correction of typographical errors B41J; processes for applying transfer pictures or the like B44C1/16; fluid media for correction of typographical errors by coating C09D10/00; printing textiles D06P) - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS ## Abstract A photopolymerization initiator which is a compound having a structure in which one or more carbonyl groups that link to a carbon atom are further directly bonded to an aromatic ring of an aromatic acyl group that bonds to a phosphorus atom in an acylphosphine oxide structure. A producing method of a photopolymerization initiator produces the photopolymerization initiator. In a polymerizable composition and an ink jet recording method, the photopolymerization initiator is used. Furthermore, an acylphosphine oxide compound has a partial structure represented by Formula 1 or Formula 2. ## Claims ### Claim 1 A photopolymerization initiator which is an acylphosphine oxide compound having a structure in which one or more carbonyl groups that link to a carbon atom are further directly bonded to an aromatic ring of an aromatic acyl group that bonds to a phosphorus atom in an acylphosphine oxide structure, wherein the carbon atom that links to the carbonyl group is an aliphatic carbon atom, wherein the photopolymerization initiator has a constitutional unit represented by Formula 1A, Formula 2A, or Formula 2B: wherein, in Formula 1A, Formula 2A, or Formula 2B, L's each independently represent a single bond, RP's each independently represent a hydrogen atom or an alkyl group, R1A's each independently represent a monovalent hydrocarbon group in which a part of a hydrocarbon chain may be substituted with a carbonyl group, an ester bond, an amide bond, an oxygen atom, NR, and/or a sulfur atom, and R1A is a group that links at an aliphatic carbon atom to the carbonyl group in Formula 2A, R1B represents a divalent hydrocarbon group in which a part of a hydrocarbon chain may be substituted with a carbonyl group, an ester bond, an amide bond, an oxygen atom, NR, and/or a sulfur atom, and R1B is a group that links at an aliphatic carbon atom to the carbonyl group in Formula 2B, R represents a hydrogen atom, an alkyl group, or an aryl group, R2 to R4 each independently represent an alkyl group, an aryl group, or an alkoxy group, m1 represents 3, m2 represents an integer of 0 to 5, and p represents an integer of 0 to 3. ### Claim 2 (depends on 1) The photopolymerization initiator according to claim 1, wherein Formula 1A is Formula 1C, and Formula 2A is Formula 2C: wherein, in Formula 1C and Formula 2C, RP's each independently represent a hydrogen atom or a methyl group, R1A's each independently represent a monovalent hydrocarbon group in which a part of a hydrocarbon chain may be substituted with a carbonyl group, an ester bond, an amide bond, an oxygen atom, NR, and/or a sulfur atom, R represents a hydrogen atom, an alkyl group, or an aryl group, R2 to R4 each independently represent an alkyl group, an aryl group, or an alkoxy group, m1 represents 3, m2 represents an integer of 0 to 5, and p represents an integer of 0 to 3. ### Claim 3 (depends on 1) The photopolymerization initiator according to claim 1 which has two or more acylphosphine oxide structures in a molecule. ### Claim 4 (depends on 3) The photopolymerization initiator according to claim 3, wherein a linking group that links two or more of the acylphosphine oxide structures together does not have any of an amino bond, a thioether bond, and a halogen atom. ### Claim 5 (depends on 1) The photopolymerization initiator according to claim 1, wherein a molecular weight or a weight-average molecular weight is 300 or more and 10,000 or less. ### Claim 6 (depends on 1) A polymerizable composition comprising: the photopolymerization initiator according to claim 1; and a polymerizable compound. ### Claim 7 (depends on 6) An inkjet recording method comprising: a step of jetting the polymerizable composition according to claim 6 onto a recording medium using an ink jet method; and a step of curing the polymerizable composition by irradiating the jetted polymerizable composition with active radiation. ### Claim 8 (depends on 1) A producing method of the photopolymerization initiator according to claim 1, the method comprising: a step of reacting an acylphosphine oxide compound having one or more aromatic acyl groups that bond to a phosphorus atom with an acid halide or an acid anhydride in the presence of a Lewis acid.