# US 10,307,343 B2 · Polymerizable dental material with a phase transfer catalyst > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,307,343 B2 - Document ID: US10307343B2 - Status: Granted - Kind: B2 - Application number: 15/064,397 - Filed: 2016-03-08 - Published: 2016-09-15 - Granted: 2019-06-04 - Earliest claimed: 2015-03-09 - Assignees: Kettenbach GmbH & Co. KG - Applicants: Kettenbach GmbH & Co. KG - Inventors: Alexander Bublewitz; Alexander Theis - Web page: https://patentgrep.com/patent/US10307343B2 ## CPC - A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds - A61K 6/60: comprising organic or organo-metallic additives - A61K 6/61: Cationic, anionic or redox initiators - A61K 6/62: Photochemical radical initiators - A61K 6/64: Thermal radical initiators - 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) ## Abstract The invention relates to a polymerizable dental material containing a catalyst paste (A) and a base paste (B), wherein the catalyst paste (A) contains at least one organic peroxygen compound, at least one radically polymerizable organic (meth)acrylic monomer and at least one filler, and wherein the base paste (B) contains at least one radically polymerizable organic (meth)acrylic monomer, an amine as co-initiator of the radical polymerization, at least one filler and at least one salt-like, water-soluble, powdery reduction agent dispersed therein, wherein the catalyst paste (A) and/or the base paste (B) contains at least one phase transfer catalyst that is selected from the group consisting of the ammonium, phosphonium and/or sulfonium salts that contain an inorganic or organic anion, provided that the phase transfer catalyst—in the event of organic anions—contains only those having 1-4 carbon atoms, and that anions of sulfinic acids are precluded. ## Claims ### Claim 1 A two-part dental material, containing a catalyst paste (A) and a base paste (B) separate from the catalyst paste (A), wherein the catalyst paste (A) contains at least one organic peroxygen compound, at least one radically polymerizable organic (meth)acrylic monomer selected from the group consisting of 2-hydroxyethylmethacrylate, di- and higher acrylates, di- and higher acrylamides, di- and higher methacrylates and di- and higher methacrylamides, and at least one filler, and wherein the base paste (B) contains at least one radically polymerizable organic (meth)acrylic monomer, an amine as co-initiator of the radical polymerization, at least one filler, and at least one salt-like, water-soluble and powdery reduction agent that is dispersed therein, and wherein only the catalyst paste (A) contains at least one phase transfer catalyst that is selected from the group consisting of ammonium, phosphonium, and/or sulfonium salts that contain an inorganic or organic anion, provided that the phase transfer catalyst—in the case of organic anions—contains only those having 1-4 carbon atoms, and that the anions of sulfinic acids are precluded. ### Claim 2 (depends on 1) The two-part dental material as recited in claim 1, wherein the at least one, salt-like, water-soluble and powdery reduction agent is selected from the group consisting of sulfites. ### Claim 3 (depends on 1) The two-part dental material as recited in claim 1, wherein the proportion of the at least one phase transfer catalyst is 0.01 to 5 percent by weight relative to the total mass of the catalyst paste (A). ### Claim 4 (depends on 1) The two-part dental material as recited in claim 1, wherein the co-initiator of the radical polymerization is a primary, secondary, or tertiary amine. ### Claim 5 (depends on 1) The two-part dental material as recited in claim 1, wherein such is dual-hardening and that additionally, at least one photoinitiator is provided in the catalyst paste (A) and/or in the base paste (B). ### Claim 6 (depends on 1) The two-part dental material as recited in claim 1, wherein the at least one radically polymerizable organic (meth)acrylic monomer is selected from the group consisting of the di and higher acrylates, di and higher acrylamides, di and higher methacrylates and di and higher methacrylamides. ### Claim 7 (depends on 1) The two-part dental material as recited in claim 1, wherein the at least one radically polymerizable organic (meth)acrylic monomer is selected from the group consisting of acrylates or methacrylates containing aromatic groups, acrylates or methacrylates containing aliphatic groups, acrylates or methacrylates containing polyether groups, acrylates or methacrylates containing polyester groups, acrylates or methacrylates containing polyurethane, or combinations of two or more of these monomers. ### Claim 8 (depends on 7) The two-part dental material as recited in claim 7, wherein the at least one radically polymerizable organic (meth)acrylic monomer is selected from the group of monomers consisting of Bisphenol A diacrylate, Bisphenol A dimethacrylate, bisphenol glycidyl acrylate, bisphenol glycidyl methacrylate (Bis-GMA), ethoxylated Bisphenol A diacrylate, ethoxylated Bisphenol A dimethacrylate, 1,6-bis(acryloxy-2-ethoxycarbonylamino)-2,4,4-trimethyl-hexane, 1,6-bis(methacryloxy-2-ethoxy-carbonylamino)-2,4,4-trimethyl-hexane (UDMA), trimethylolpropane triacrylate trimethylolpropane trimethacrylate (TMPTMA), 2-hydroxyethylacrylate, 2-hydroxyethyl methacrylate (HEMA), glycerin-1,3-acrylate, glycerin-1,3-dimethacrylate (GDMA), dodecanediol diacrylate, dodecanediol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene diacrylate, tetraethylene glycol dimethacrylate or combinations of two or more of these monomers. ### Claim 9 (depends on 1) The two-part dental material as recited in claim 1, wherein the radically polymerizable organic (meth)acrylic monomers are free of any structural units having bisphenol A residues. ### Claim 10 (depends on 1) The two-part dental material as recited in-claim 1, wherein the organic peroxygen compound is selected from the group consisting of organic peroxides. ### Claim 11 (depends on 1) The two-part dental material as recited in claim 1, wherein the anion of the phase transfer catalyst is selected from the group consisting of halogenides, hydroxides, anions of inorganic acids, pseudo halogenide anions or halogen complexes of aluminate, silicate or phosphate, or anions of organic acids having 1-4 carbon atoms, excluding anions of sulfinic acids. ### Claim 12 (depends on 11) The two-part dental material as recited in claim 11, wherein the anion of the phase transfer catalyst is selected from the group consisting of fluoride, chloride, bromide, iodide, hydroxide, sulfate, hydrogen sulfate, dihydrogen sulfate, phosphate, phosphonate, borate, chlorate, perchlorate, nitrite, nitrate, hydrogen carbonate, carbonate, tetrafluoroborate, tetrachloroaluminate, hexafluorosilicate, hexachlorophosphate, formate, acetate, butyrate, fumarate, maleate, glutarate, lactate, malate, malonate, oxalate, pyruvate or tartrate. ### Claim 13 (depends on 1) The two-part dental material as recited in claim 1, wherein the phase transfer catalyst is an ammonium salt having the cation NR1R2R3R4, wherein R1, R2, R3 and R4—independent of each other—mean C1 to C20 alkyl, C1 to C20 alkyl halogenide, C1 to C20 alkyloxy, C1 to C20 hydroxyalkyl, C2 to C20 alkenyl, C2 to C20 alkenyloxy, C2 to C20 alkinyl, C2 to C20 alkinyloxy, C2 to C20 alkyl ester, aryl, aryloxy, aralkyl, aralkyloxy, alkylaryl and/or alkylaryloxy. ### Claim 14 (depends on 1) The two-part dental material as recited in claim 1, wherein the phase transfer catalyst is a phosphonium salt having the cation PR1R2R3R4, wherein R1, R2, R3 and R4—independent of each other—mean C1 to C20 alkyl, C1 to C20 alkyl halogenide, C1 to C20 alkyloxy, C2 to C20 alkenyl, C2 to C20 alkenyloxy, C2 to C20 alkinyl, C2 to C20 alkinyloxy, C2 to C20 alkyl ester, aryl, aryloxy, aralkyl, aralkyloxy, alkylaryl and/or alkylaryloxy. ### Claim 15 (depends on 1) The two-part dental material as recited in claim 1, wherein the phase transfer catalyst is a sulfonium salt having the cation SR1R2R3, wherein R1, R2 und R3—independent of each other—mean C1 to C20 alkyl, C1 to C20 alkyl halogenide, C1 to C20 alkyloxy, C2 to C20 alkenyl, C2 to C20 alkenyloxy, C2 to C20 alkinyl, C2 to C20 alkinyloxy, C2 to C20 alkyl ester, aryl, aryloxy, aralkyl, aralkyloxy, alkylaryl and/or alkylaryloxy. ### Claim 16 (depends on 1) The two-part dental material as recited in claim 1, wherein the phase transfer catalyst is tetrabutylammonium hydrogen sulfate, tetramethylammonium hydrogen sulfate, tetrahexylammonium hydrogen sulfate, bis[tetrakis(hydroxymethyl)-phosphonium] sulfate, tetraphenylphosphonium chloride, 1-ethyl-2,3-dimethylimidazoliumimidazolium ethylsulfate, cetyltrimethylammonium hydrogen sulfate, (vinylbenzyl) trimethylammonium chloride, tetrabutylammonium chloride and/or tetrabutylammonium tetrafluoroborate. ### Claim 17 (depends on 1) A cured dental material obtained by a method comprising providing the two-step dental material of claim 1, mixing the components A and B at a ratio of 1:20 to 1:1 and polymerizing of the resulting polymerizable dental material. ### Claim 18 (depends on 17) The cured dental material as recited in claim 17, in the form of a core buildup material, a cement composite and/or a bulk fill composite. ### Claim 19 (depends on 1) A method for making a dental material selected from a core buildup material, a polymerizable composite cement and a bulk fill composite for producing core structures, mountings and/or tooth fillings, the method comprising providing the two-part dental material of claim 1, and including the components A and B in the dental material. ### Claim 20 (depends on 1) An add-on system (kit of parts) comprising the two-part dental material as recited in claim 1 and a dental adhesive. ### Claim 21 (depends on 7) The two-part dental material of claim 7, wherein the at least one radically polymerizable organic (meth)acrylic monomer has at least two acrylate and/or methacrylate groups. ### Claim 22 (depends on 1) The two-part dental material of claim 1, wherein the phase transfer catalyst is an ammonium salt having at least one C4 residue. ### Claim 23 (depends on 1) The two-part dental material of claim 1, wherein the phase transfer catalyst has an organic anion having 1-4 carbon atoms. ### Claim 24 (depends on 1) The two-part dental material of claim 1, wherein the phase transfer catalyst has an inorganic anion selected from hydroxides, anions of inorganic acids, pseudohalogenide anions and halogen complexes of aluminate, borate, silicate and phosphate.