# US 12,180,317 B2 · Polymerizable composition and hydrophilizing treatment method > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,180,317 B2 - Document ID: US12180317B2 - Status: Granted - Kind: B2 - Application number: 17/678,350 - Filed: 2022-02-23 - Published: 2022-08-25 - Granted: 2024-12-31 - Earliest claimed: 2021-02-24 - Assignees: Tokyo Ohka Kogyo Co., Ltd. - Applicants: Tokyo Ohka Kogyo Co., Ltd. - Inventors: Takahiro Senzaki - Web page: https://patentgrep.com/patent/US12180317B2 ## CPC - C08F 236/20: unconjugated - 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} - C08F 226/02: by a single or double bond to nitrogen - C09D 147/00: Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Coating compositions based on derivatives of such polymers (C09D145/00 takes precedence; based on conjugated diene rubbers C09D109/00 - C09D121/00) - 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 To provide a polymerizable composition capable of forming a thick hydrophilic resin coating having high hardness and excellent durability on the surface of an object to be treated, which is a surface treatment object, and a hydrophilizing treatment method in which the polymerizable composition is used. In a polymerizable composition including a polymerizable compound (A), a polymerization initiator (B), inorganic fine particles (C) and a solvent (S), a polymerizable betaine compound (A1) having an ethylenic unsaturated double bond and a betaine structure and an adhesive polymerizable compound (A2) having an ethylenic unsaturated double bond and a specific type of adhesive group are used as the polymerizable compound (A); a water-soluble radical polymerization initiator (B1) is used as the polymerization initiator (B); and inorganic fine particles (C) having a functional group capable of forming a covalent bond with a polymer of the polymerizable compound (A) are used. ## Claims ### Claim 1 A polymerizable composition comprising: a polymerizable compound (A); a polymerization initiator (B); inorganic fine particles (C); and a solvent(S), wherein the polymerizable compound (A) comprises a polymerizable betaine compound (A1) and an adhesive polymerizable compound (A2), the polymerizable betaine compound (A1) has an ethylenic unsaturated double bond and a betaine structure, the adhesive polymerizable compound (A2) has an ethylenic unsaturated double bond and at least one adhesive group selected from the group consisting of a hydrolysable silyl group, −NH2, a carboxy group, a cyano group and a hydroxyl group, a ratio of a mass of the adhesive polymerizable compound (A2) with respect to a mass of the polymerizable compound (A) is 0.1% by mass or more and 5% by mass or less, the polymerization initiator (B) comprises a water-soluble radical polymerization initiator (B1), the inorganic fine particles (C) have an average particle diameter of 5 nm or more and 5000 nm or less based on a specific surface area of the inorganic fine particles (C) obtained by BET method, the inorganic fine particles (C) have a functional group capable of forming a covalent bond with a polymer of the polymerizable compound (A), and the solvent(S) is an aqueous solution of alcohol. ### Claim 2 (depends on 1) The polymerizable composition according to claim 1, wherein the inorganic fine particles (C) are silica particles. ### Claim 3 (depends on 1) The polymerizable composition according to claim 1, wherein a ratio of a mass of the inorganic fine particles (C) with respect to a mass obtained by subtracting a mass of the solvent(S) from a mass of the polymerizable composition is 20% by mass or more and 80% by mass or less. ### Claim 4 (depends on 1) The polymerizable composition according to claim 1, wherein a ratio of a mass of the inorganic fine particles (C) with respect to a mass of the polymerizable compound (A) is 10% by mass or more and 200% by mass or less. ### Claim 5 (depends on 4) The polymerizable composition according to claim 4, wherein the ratio of the mass of the inorganic fine particles (C) with respect to the mass of the polymerizable compound (A) is 50% by mass or more and 150% by mass or less. ### Claim 6 (depends on 1) The polymerizable composition according to claim 1, wherein a solid content concentration of the polymerizable composition is 0.1% by mass or more and 20% by mass or less. ### Claim 7 (depends on 1) The polymerizable composition according to claim 1, wherein the water-soluble radical polymerization initiator (B1) is a water-soluble azo polymerization initiator. ### Claim 8 (depends on 1) The polymerizable composition according to claim 1, wherein the polymerizable betaine compound (A1) is a compound represented by the following formula (a1-ii), wherein R3, R4, and R5 are each independently a hydrocarbon group having an ethylenic unsaturated double bond, or a hydrocarbon group having 1 or more and 10 or less carbon atoms, at least one of R3, R4, or R5 is the hydrocarbon group having the ethylenic unsaturated double bond, R6 is a divalent hydrocarbon group having 1 or more and 10 or less carbon atoms, and Ris an anionic group. ### Claim 9 (depends on 1) The polymerizable composition according to claim 1, wherein the inorganic fine particles (C) are silica particles having a silanol group on surfaces thereof. ### Claim 10 (depends on 1) A hydrophilizing treatment method for hydrophilizing a surface of an object to be treated, the method comprising: applying the polymerizable composition according to claim 1 to form a coating film on the surface of the object to be treated; and heating the coating film to form a coating on the surface of the object to be treated. ### Claim 11 (depends on 10) The hydrophilizing treatment method according to claim 10, wherein the coating has a film thickness of 10 nm or more and 2000 nm or less. ### Claim 12 A polymerizable composition comprising: a polymerizable compound (A); a polymerization initiator (B); inorganic fine particles (C); and a solvent(S), wherein the polymerizable compound (A) comprises a polymerizable betaine compound (A1) and an adhesive polymerizable compound (A2), the polymerizable betaine compound (A1) has an ethylenic unsaturated double bond and a betaine structure, the adhesive polymerizable compound (A2) is an unsaturated group-containing silicon compound (A2-1) having an ethylenic unsaturated double bond and a hydrolysable silyl group, a ratio of a mass of the adhesive polymerizable compound (A2) with respect to a mass of the polymerizable compound (A) is 0.1% by mass or more and 5% by mass or less, the polymerization initiator (B) comprises a water-soluble radical polymerization initiator (B1), the inorganic fine particles (C) have an average particle diameter of 5 nm or more and 5000 nm or less based on a specific surface area of the inorganic fine particles (C) obtained by BET method, and the inorganic fine particles (C) have a functional group capable of forming a covalent bond with a polymer of the polymerizable compound (A). ### Claim 13 (depends on 12) The polymerizable composition according to claim 12, wherein the inorganic fine particles (C) are silica particles. ### Claim 14 (depends on 12) The polymerizable composition according to claim 12, wherein the polymerizable betaine compound (A1) is a compound represented by the following formula (a1-ii), wherein R3, R4, and R5 are each independently a hydrocarbon group having an ethylenic unsaturated double bond, or a hydrocarbon group having 1 or more and 10 or less carbon atoms, at least one of R3, R4, or R5 is the hydrocarbon group having the ethylenic unsaturated double bond, R6 is a divalent hydrocarbon group having 1 or more and 10 or less carbon atoms, and Ris an anionic group.