# US 8,148,571 B2 · Compound, composition comprising the same, and process for production of polymerizable amide > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,148,571 B2 - Document ID: US8148571B2 - Status: Granted - Kind: B2 - Application number: 12/443,620 - Filed: 2007-09-27 - Published: 2010-03-25 - Granted: 2012-04-03 - Earliest claimed: 2006-09-29 - Assignees: Kuraray Medical Inc. - Inventors: Takahiro Sekiguchi; Ai Hinamoto - Web page: https://patentgrep.com/patent/US8148571B2 ## CPC - C07C 233/47: having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton - A61K 6/30: Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives - C07C 231/02: from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines - C07F 9/091: {with hydroxyalkyl compounds with further substituents on alkyl} - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - 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) - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) ## Abstract A novel compound (I) represented by the following formula (1) is provided which is suitable for a dental composition and has a polymerizable group, a carboxyl group and a phosphoric acid group. A method for producing a polymerizable amide is provided, which method can make a condensation reaction of a carboxylic acid with an amine to proceed easily and is excellent in safety: wherein R1, R2 and R3 each independently are a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent; (A) and (B) are each any constituent unit; m is an integer of from 1 to 3; n is an integer of from 1 to 3; R4 is an organic group having 1 to 40 carbon atoms which may have a substituent; R5 is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, R6 and R7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a metal atom. ## Claims ### Claim 1 A compound (I) represented by formula (1): wherein R1, R2 and R3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms; A is —CONH— or —COO—; B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—; m is an integer of from 1 to 3; n is an integer of from 1 to 3; R4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms; R5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms; R6 and R7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom. ### Claim 2 (depends on 1) The compound (I) of claim 1, wherein R1 and R2 are each a hydrogen atom and R3 is a hydrogen atom or a methyl group. ### Claim 3 (depends on 1) The compound (I) of claim 1, wherein A is —CONH—. ### Claim 4 (depends on 1) The compound (I) of claim 1, wherein B is —CONH—. ### Claim 5 (depends on 1) The compound (I) of claim 1, wherein R5 is one selected from the group consisting of —CH2-Ph-, —CH(CH3)— and —CH2—. ### Claim 6 A composition comprising a compound (I) represented by formula (1): wherein R1, R2 and R3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms; A is one selected from the group consisting of —CONH—, —COO—, —OCO—, —O—, —S—, —CH2O—, —CH2S—, —C6H4O—, —C6H4CONH—, —C6H4NHCO—, —C6H4COO—, —C6H4OCO— and —CONHCO—; B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—; m is an integer of from 1 to 3; n is an integer of from 1 to 3; R4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms; R5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms; R6 and R7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom, and a polymerizable monomer (II) which is other than the compound (I) and which can be copolymerized with the compound (I). ### Claim 7 A composition comprising compound (I) represented by formula (1): wherein R1, R2 and R3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms; A is one selected from the group consisting of —CONH—, —COO—, —OCO—, —O—, —S—, —CH2O—, —CH2S—, —C6H4O—, —C6H4CONH—, —C6H4NHCO—, —C6H4COO—, —C6H4OCO— and —CONHCO—; B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—; m is an integer of from 1 to 3; n is an integer of from 1 to 3; R4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms; R5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms; R6 and R7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom, said composition further comprising at least one of the following: a polymerization initiator (III), a polymerization accelerator (IV), and a filler (V). ### Claim 8 (depends on 6) The composition of claim 6, wherein the polymerizable monomer (II) is a (meth)acrylate compound. ### Claim 9 (depends on 7) The composition of claim 7, which comprises said polymerization initiator (III). ### Claim 10 (depends on 7) The composition of claim 7, which comprises said polymerization accelerator (IV). ### Claim 11 (depends on 7) The composition of claim 7, which comprises said filler (V). ### Claim 12 (depends on 7) The composition of claim 7, which comprises said solvent (VI). ### Claim 13 (depends on 12) The composition of claim 12, wherein the solvent (VI) comprises water (VII). ### Claim 14 (depends on 6) A primer comprising the composition of claim 6, a compound (I) represented by formula (1): wherein R1, R2 and R3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms; A is one selected from the group consisting of —CONH—, —COO—,—OCO—, —O—, —S—, —CH2O—, —CH2S—, —C6H4O—, —C6H4CONH—, 13 C6H4NHCO—, —C6H4COO—, —C6H4OCO— and —CONHCO—; B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—; m is an integer of from 1 to 3; n is an integer of from 1 to 3; R4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms; R5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms; R6 and R7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom. ### Claim 15 (depends on 6) A bonding material comprising the composition of claim 6, a compound (I) represented by formula (1): wherein R1, R2 and R3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms: A is one selected from the group consisting of —CONH—, —COO—, —OCO—, —O—, —S—, —CH2O—, —CH2S—, —C6H4O—, —C6H4CONH—, —C6 H4NHCO—, —C6COO—, —C6H4OCO— and —CONHCO—; B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—; m is an integer of from 1 to 3; n is an integer of from 1 to 3; R4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms; R5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms; R6 and R7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom. ### Claim 16 (depends on 6) A cement comprising the composition of claim 6, a compound (I) represented by formula (1): wherein R1, R2 and R3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms; A is one selected from the group consisting of —CONH—, —COO—, —OCO—, —O—, —S—, —CH2O—, —CH2S—, —C6H4O—, —C6H4CONH—, —C6H4NHCO—, —C6H4COO—, —C6H4OCO— and —CONHCO—; B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—; m is an integer of from 1 to 3; n is an integer of from 1 to 3; R4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms; R5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms; R6 and R7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom. ### Claim 17 (depends on 6) A composite resin comprising the composition of claim 6, a compound (I) represented by formula (1): wherein R1, R2 and R3 each independently are a hydrogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a substituted hydrocarbon group having 1 to 20 carbon atoms; A is one selected from the group consisting of —CONH—, —COO—, —OCO—, —O—, —S—, —CH2O—, —CH2S—, —C6H4O—, C6H4CONH—, —C6H4NHCO—, —C6H4COO—, —C6H4OCO— and —CONHCO—; B is one selected from the group consisting of —CONH—, —NHCO—, —COO— and —OCO—; m is an integer of from 1 to 3; n is an integer of from 1 to 3; R4 is an organic group having 1 to 40 carbon atoms or a substituted organic group having 1 to 40 carbon atoms; R5 is a hydrocarbon group having 1 to 20 carbon atoms or a substituted hydrocarbon group having 1 to 20 carbon atoms; R6 and R7 each independently are a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a substituted hydrocarbon group having 1 to 20 carbon atoms, or a metal atom. ### Claim 18 (depends on 4) A method for producing the compound (I) of claim 4, comprising reacting a carboxylic acid represented by formula (2) by condensation reaction with an amine represented by formula (3): wherein R1, R2, R3, R4, (A), m and n are the same as those of the formula (1), wherein R5, R6 and R7 are the same as those of the formula (1). ### Claim 19 (depends on 18) The method for producing the compound (I) of claim 18, wherein the carboxylic acid contains a (meth)acryl group. ### Claim 20 (depends on 18) The method for producing the compound (I) of claim 18, wherein a condensing agent present during said reacting is a triazine compound. ### Claim 21 (depends on 4) A method for producing the compound (I) of claim 4, comprising reacting an acid halide represented by formula (4) with an amine represented by formula (3): wherein R1, R2, R3, R4, (A), m and n are the same as those of the formula (1), and X is a halogen atom, wherein R5, R6 and R7 are the same as those of the formula (1). ### Claim 22 (depends on 21) The method for producing the compound (I) of claim 21, wherein the acid halide contains a (meth)acryl group. ### Claim 23 (depends on 18) The method for producing the compound (I) claim 18, wherein the amine is a phosphate of an amino acid. ### Claim 24 (depends on 23) The method for producing the compound (I) of claim 23, wherein the amine is one selected from the group consisting of phosphoserine, phosphothreonine and phosphotyrosine. ### Claim 25 (depends on 21) The method for producing the compound (I) claim 21, wherein the amine is a phosphate of an amino acid. ### Claim 26 (depends on 1) The compound (I) of claim 1, wherein A is —COO—.