Patents by Inventor Joachim E. Klee
Joachim E. Klee has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Publication number: 20190117522Abstract: Dental composition comprising (a) a homogeneous phase comprising monomer combinations (i) and (ii), (i) and (iii), (ii) and (iii), or (i), (ii) and (iii), or comprising monomer (iii), wherein (i) represents one or more compounds having one or more radically polymerizable carbon-carbon double bonds; (ii) represents one or more compounds having one or more cationically polymerizable groups; and (iii) represents one or more compounds having a combination of one or more radically polymerizable carbon-carbon double bonds and one or more cationically polymerizable groups; (b) an initiator system comprising (iv) one or more radical polymerization initiator of the following formula (I): wherein M is Ge or Si; R1, R2 and R3 may be the same or different, independently represent an organic group, and R4 represents a hydrogen atom, an organic or organometallic group; provided that when R4 is a hydrogen atom, the initiator system further comprises a sensitizer compound having a light absorption maximum in the rangType: ApplicationFiled: April 7, 2017Publication date: April 25, 2019Applicant: DENTSPLY SIRONA inc.Inventors: Joachim E. Klee, Maximilian MAIER, Christoph P. FIK, Jscques LALEVEE, Jean Pierre FOUASSIER, Fabrice MORLET-SAVARY, Celine DIETLIN, Mariem BOUZRATI-ZERELLI
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Patent number: 10188587Abstract: Dental composite comprising (i) a polymerizable composition obtainable by reacting a mixture comprising: (a) x equivalents of one or more compounds of the following formula (I): wherein L? is an (l+1)-valent hydrocarbon group which may contain in its backbone 1 to 3 heteroatoms selected from oxygen atoms and sulfur atoms and which may be substituted by one or more hydroxyl groups or groups —COOL? wherein L? is a polymerizable moiety; l is an integer of from 1 to 3; (b) y equivalents of one or more compounds of the following formula (IIa), (IIb) and/or (IIc): wherein n is an integer of from 1 to 3, Y may be present or absent, and when present represents a carbonyl group; Y? independently may be present or absent, represents a carbonyl group; Rm which may be the same or different represent 1 to 3 substituents selected from halogen atoms, alkyl groups, and alkoxy groups, or wherein two Rm form together with the carbon atoms of the ring to which they are bonded an annelated aromatic riType: GrantFiled: December 4, 2014Date of Patent: January 29, 2019Assignee: DENTSPLY SIRONA Inc.Inventors: Joachim E. Klee, Maximilian Maier, Christian Scheufler
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Patent number: 10123948Abstract: A dental cement hardened by a cement reaction involving the specific polymerizable polyacidic polymer and optionally additional crosslinkable groups, has reduced shrinkage and improved mechanical properties, in particular with regard to flexural strength and fracture toughness. Moreover, the specific polymerizable polyacidic polymer of the present invention contains a high number of acidic groups which is not reduced by the presence of polymerizable moieties, whereby water solubility of the uncured polymer is not impaired by the presence of the polymerizable moieties.Type: GrantFiled: January 29, 2016Date of Patent: November 13, 2018Assignee: DENTSPLY SIRONA Inc.Inventors: Joachim E Klee, Helmut Ritter, Sven Pohle, Oliver Elsner, Mareike Bardts
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Patent number: 10117810Abstract: Dental cement composition comprising (i) a particulate filler reactive with a polyacid in a cement reaction; (ii) a water-soluble polymerizable compound of the following formula (1), AXn (1) wherein A is a linker group containing at least n nitrogen atoms and optionally one or more acidic groups, X are moieties containing a polymerizable double bond and forming an amide bond with a nitrogen atom of A, which X may be the same or different and are represented by the following formula (2) wherein R1 and R2 are independent from each other and represent a hydrogen atom, a C1-6 alkyl group or a group —(CH2)m—Z, wherein Z is COOM, OPO3M2, PO3M2, SO3M, and M is independently a hydrogen atom or a metal atom, and m is an integer of from 0 to 6, L is a bond or a C1-6 alkylene group; and n is an integer of at least 1; provided that at least one X cannot be a (meth)acryl group; and (iii) an initiator system; optionally a polyacidic polymer having polymerizable double bonds; and optionally water.Type: GrantFiled: October 18, 2011Date of Patent: November 6, 2018Assignee: Dentsply International Inc.Inventors: Simon Stelzig, Joachim E. Klee, Andreas Facher, Christoph Weber
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Publication number: 20180303722Abstract: The present invention relates to a dental composition comprising a specific polymerization initiator system comprising a compound having an acylsilyl- or acylgermanyl-group. The present invention also relates the use of the compound having an acylsilyl- or acylgermanyl group for the preparation of a dental composition.Type: ApplicationFiled: October 7, 2016Publication date: October 25, 2018Applicant: DENTSPLY SIRONA Inc.Inventors: Joachim E. KLEE, Florian SZILLAT, Maximilian MAIER, Helmut RITTER, Jacques LALEVEE, Jean Pierre FOUASSIER, Fabrice MORLET-SAVARY, Celine DIETLIN, Mariem BOUZRATI-ZERELLI, Christoph P FIK
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Publication number: 20180289592Abstract: The present invention relates to a dental composition comprising an initiator system comprising a sensitizer compound having an acylsilyl- or acylgermyl-group and a specific coinitiator compound. The present invention also relates to an initiator system consisting essentially of the sensitizer compound having an acylsilyl- or acylgermyl-group and a coinitiator compound wherein a C—H bond dissociation energy is less than 95 Kcal/mol. Furthermore, the present invention relates to the use of this initiator system for the preparation of a dental composition.Type: ApplicationFiled: October 10, 2016Publication date: October 11, 2018Applicant: DENTSPLY SIRONA Inc.Inventors: Joachim E. KLEE, Florian SZILLAT, Maximilian MAIER, Helmut RITTER, Jacques LALEVEE, Jean Pierre FOUASSIER, Fabrice MORLET-SAVARY, Celine DIETLIN, Mariem BOUZRATI-ZERELLI, Christoph P. FIK
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Publication number: 20180228701Abstract: A process for producing a water-soluble, hydrolysis-stable, polymerizable polymer, comprising a) a step of copolymerizing a mixture comprising (i) a first copolymerizable monomer comprising at least one optionally protected carboxylic acid group and a first polymerizable organic moiety, and (ii) a second copolymerizable monomer comprising one or more optionally protected primary and/or secondary amino groups and a second polymerizable organic moiety, for obtaining an amino group containing copolymer; b) a step of coupling to the amino group containing copolymer a compound having a polymerizable moiety and a functional group reactive with an amino group of repeating units derived from the second copolymerizable monomer in the amino group containing copolymer obtained in the first step wherein the optionally protected amino group is deprotected, so that polymerizable pendant groups are linked to the backbone by hydrolysis-stable linking groups, and, optionally, a step of deprotecting the protected carboxylic acType: ApplicationFiled: April 12, 2018Publication date: August 16, 2018Applicant: DENTSPLY SIRONA Inc.Inventors: Joachim E. KLEE, Helmut RITTER, Maximilliam MAIER, Julia GANSEL, Andreas FACHER, Oliver ELSNER, Sven POHLE
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Patent number: 10040969Abstract: A process for the preparation of composite filler particles, comprising: (a) coating a particulate filler having a median particle size (D50) of from 1 to 1200 nm; (b) agglomerating the coated particulate filler, for providing a granulation of the coated particulate filler wherein the granulation contains the coated particulate filler particles whereby the at least one coating layer may be crosslinked by crosslinking groups obtained by reacting the reactive groups and optionally a further crosslinking agent.Type: GrantFiled: October 1, 2015Date of Patent: August 7, 2018Assignee: DENTSPLY SIRONA Inc.Inventors: Simon Stelzig, Jörg Kempter, Stephanie Noerpel, Joachim E. Klee, Andreas Facher, Uwe Walz, Christoph Weber
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Patent number: 9999576Abstract: An aqueous dental glass ionomer composition comprising (a) a reactive particulate glass, (b) a linear or branched polymer comprising acidic groups, which is reactive with the particulate glass in a cement reaction, whereby the linear or branched polymer comprising acidic groups has a polymer backbone and optionally pendant groups, (c) optionally dispersed nanoparticles comprising grafted linear or branched polymer chains comprising acidic groups, and having a polymer backbone characterized in that a polymer backbone of the linear or branched polymer of component (b) and/or, if present, the grafted linear or branched polymer chains of component (c) are obtainable a process comprising (i) cyclopolymerizing or cyclocopolymerizing one or more compounds of the following formula (I):Type: GrantFiled: May 15, 2017Date of Patent: June 19, 2018Assignee: Dentsply Detrey GMBHInventors: Joachim E. Klee, Oliver Elsner, Sven Pohle, Helmut Ritter, Dominika Bernert
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Patent number: 9993395Abstract: A process for producing a water-soluble, hydrolysis-stable, polymerizable polymer, comprising a) a step of copolymerizing a mixture comprising (i) a first copolymerizable monomer comprising at least one optionally protected carboxylic acid group and a first polymerizable organic moiety, and (ii) a second copolymerizable monomer comprising one or more optionally protected primary and/or secondary amino groups and a second polymerizable organic moiety, for obtaining an amino group containing copolymer; b) a step of coupling to the amino group containing copolymer a compound having a polymerizable moiety and a functional group reactive with an amino group of repeating units derived from the second copolymerizable monomer in the amino group containing copolymer obtained in the first step wherein the optionally protected amino group is deprotected, so that polymerizable pendant groups are linked to the backbone by hydrolysis-stable linking groups, and, optionally, a step of deprotecting the protected carboxylic acType: GrantFiled: December 20, 2011Date of Patent: June 12, 2018Assignee: DENTSPLY SIRONA Inc.Inventors: Joachim E. Klee, Helmut Ritter, Maximilliam Maier, Julia Gansel, Andreas Facher, Oliver Elsner, Sven Pohle
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Patent number: 9931280Abstract: A dental composite composition is disclosed that includes a polymerizable resin, filler particles, and at least one polymerizable stable radical. A variety of polymerizable stable radicals may be employed, including those that have a 2,2,6,6-tetramethylpiperidinyl-1-oxyl moiety. Compositions as described herein exhibit excellent mechanical strength, hardness, and flexural modulus, while also significantly decreasing shrinkage stress caused by polymerization.Type: GrantFiled: October 3, 2014Date of Patent: April 3, 2018Assignee: Dentsply Sirona Inc.Inventors: Hui Lu, Xiaoming Jin, Joachim E. Klee, Bernard Koltisko
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Publication number: 20180071175Abstract: Dental cement composition comprising (i) a particulate filler reactive with a polyacid in a cement reaction; (ii) a water-soluble polymerizable compound of the following formula (1), AXn (1) wherein A is a linker group containing at least n nitrogen atoms and optionally one or more acidic groups, X are moieties containing a polymerizable double bond and forming an amide bond with a nitrogen atom of A, which X may be the same or different and are represented by the following formula (2) wherein R1 and R2 are independent from each other and represent a hydrogen atom, a C1-6 alkyl group or a group —(CH2)m—Z, wherein Z is COOM, OPO3M2, PO3M2, SO3M, and M is independently a hydrogen atom or a metal atom, and m is an integer of from 0 to 6, L is a bond or a C1-6 alkylene group; and n is an integer of at least 1; provided that at least one X cannot be a (meth)acryl group; and (iii) an initiator system; optionally a polyacidic polymer having polymerizable double bonds; and optionally water.Type: ApplicationFiled: October 18, 2011Publication date: March 15, 2018Applicant: DENTSPLY INTERNATIONAL INC.Inventors: Simon Stelzig, Joachim E. Klee, Andreas Facher, Christoph Weber
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Patent number: 9895294Abstract: A temporary root canal sealer dispersion having a pH of at least 9 and comprising: (i) an aqueous dispersion medium comprising an oligomer and/or polymer having Lewis basic groups, and optionally a hydroxide of an alkali metal and/or a hydroxide of an alkaline earth metal, and (ii) a dispersed phase comprising a radio-opaque filler, wherein the weight ratio of oligomer and/or polymer having Lewis basic groups to hydroxide of an alkali metal and/or hydroxide of an alkaline earth metal is at least 0.5 when said aqueous dispersion medium comprises a hydroxide of an alkali metal and/or a hydroxide of an alkaline earth metal.Type: GrantFiled: March 18, 2010Date of Patent: February 20, 2018Assignee: DENTSPLY SIRONA INC.Inventors: Joachim E. Klee, Christoph Weber, Andreas E. Grützner
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Patent number: 9775786Abstract: A one-part self-etching, self-priming dental adhesive having a pH of at most 2, which comprises an aqueous mixture containing (i) one or more polymerizable monomers optionally containing an acidic group, (ii) optionally one or more organic or inorganic acids, (iii) a polymerization initiator, and (iv) a thermal polymerisation inhibitor of the following formula (I): ?wherein R?1 represents a hydrogen atom, or a saturated hydrocarbon group having 1 to 18 carbon atoms. R?2, which may be the same or different if more than one R?2 is present, independently represent a saturated hydrocarbon group having 1 to 18 carbon atoms, and c represents an integer of from 1 to 4.Type: GrantFiled: December 23, 2014Date of Patent: October 3, 2017Inventors: Joachim E Klee, Uwe Lehmann
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Patent number: 9770395Abstract: Non-aqueous dental adhesive comprising a mixture containing (i) one or more polymerizable monomers optionally containing an acidic group, (ii) a polymerization initiator, and (iii) a thermal polymerization inhibitor of the following formula (I) wherein R?1 represents a hydrogen atom, or a saturated hydrocarbon group having 1 to 18 carbon atoms. R?2, which may be the same or different if more than one R?2 is present, independently represent a saturated hydrocarbon group having 1 to 18 carbon atoms, and c represents an integer of from 1 to 4, and (iv) optionally an organic solvent.Type: GrantFiled: September 14, 2009Date of Patent: September 26, 2017Assignee: Dentsply Detrey GmbHInventors: Joachim E. Klee, Uwe Lehmann
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Publication number: 20170252271Abstract: An aqueous dental glass ionomer composition comprising (a) a reactive particulate glass, (b) a linear or branched polymer comprising acidic groups, which is reactive with the particulate glass in a cement reaction, whereby the linear or branched polymer comprising acidic groups has a polymer backbone and optionally pendant groups, (c) optionally dispersed nanoparticles comprising grafted linear or branched polymer chains comprising acidic groups, and having a polymer backbone characterized in that a polymer backbone of the linear or branched polymer of component (b) and/or, if present, the grafted linear or branched polymer chains of component (c) are obtainable a process comprising (i) cyclopolymerizing or cyclocopolymerizing one or more compounds of the following formula (I):Type: ApplicationFiled: May 15, 2017Publication date: September 7, 2017Inventors: Joachim E. KLEE, Oliver ELSNER, Sven POHLE, Helmut RITTER, Dominika BERNERT
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Patent number: 9682019Abstract: An aqueous dental glass ionomer composition comprising (a) a reactive particulate glass, (b) a linear or branched polymer comprising acidic groups, which is reactive with the particulate glass in a cement reaction, whereby the linear or branched polymer comprising acidic groups has a polymer backbone and optionally pendant groups, (c) optionally dispersed nanoparticles comprising grafted linear or branched polymer chains comprising acidic groups, and having a polymer backbone characterized in that a polymer backbone of the linear or branched polymer of component (b) and/or, if present, the grafted Sinear or branched polymer chains of component (c) are obtainable a process comprising (i) cyclopolymerizing or cyclocopolymerizing one or more compounds of the following formula (I).Type: GrantFiled: November 2, 2010Date of Patent: June 20, 2017Assignee: Dentsply DeTry GmbHInventors: Joachim E. Klee, Oliver Elsner, Sven Pohle, Helmut Ritter, Dominika Bernert
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Patent number: 9668944Abstract: Dental composition comprising (i) a particulate filler; (ii) a polymerizable hydrolysis-stable compound of the following formula (1) AXn wherein A is a linker group containing at least n nitrogen atoms and optionally one or more acidic groups, X are moieties containing a polymerizable double bond and forming an amide bond with a nitrogen atom of A, which X may be the same or different and are represented by the following formula (2) wherein R1 and R2 are independent from each other and represent a hydrogen atom, a C1-6 alkyl group or a group —(CH2)m—Z, wherein Z is COOM, OPO3M2, PO3M2, SO3M, and M is independently a hydrogen atom or a metal atom, and m is an integer of from 0 to 6, L is a bond, a C1-6 alkylene group; and n is an integer of at least 1; provided that at least one X cannot be a (meth)acryl group; and (iii) an initiator system.Type: GrantFiled: May 5, 2015Date of Patent: June 6, 2017Assignee: Dentsply International Inc.Inventors: Simon Stelzig, Joachim E. Klee, Andreas Facher, Christoph Weber
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Patent number: 9603780Abstract: Dental composition comprising a water-soluble polymerizable compound of the following formula (1): wherein A is a linear or branched linker group represented by the following formula (3), wherein the nitrogen atom of at least two of the termini forms an amide bond with an X moiety; wherein R? represents a hydrogen atom or a substituted or unsubstituted aliphatic or cycloaliphatic hydrocarbon group, wherein each R may be the same or different L1, L2, and L3 which may be the same or different, independently represent a single bond, or a C2-20 straight-chain, branched or cyclic hydrocarbon group optionally containing from 1 to 6 heteroatoms selected from nitrogen and oxygen in the backbone of the hydrocarbon group, and optionally from 1 to 6 functional groups selected from carboxylic acid groups or a salt thereof, hydroxyl groups, thiol groups and amino groups, and in case a plurality of L1 and L2 are present, each of L1 and L2 may be the same or different; Q1 and Q2, which may be the same or different, independType: GrantFiled: October 18, 2011Date of Patent: March 28, 2017Inventors: Simon Stelzig, Joachim E. Klee, Andreas Facher, Christoph Weber
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Publication number: 20160256363Abstract: Dental composite comprising (i) a polymerizable composition obtainable by reacting a mixture comprising: (a) x equivalents of one or more compounds of the following formula (I): wherein L? is an (l+1)-valent hydrocarbon group which may contain in its backbone 1 to 3 heteroatoms selected from oxygen atoms and sulfur atoms and which may be substituted by one or more hydroxyl groups or groups —COOL? wherein L? is a polymerizable moiety; l is an integer of from 1 to 3; (b) y equivalents of one or more compounds of the following formula (IIa), (IIb) and/or (IIc): wherein n is an integer of from 1 to 3, Y may be present or absent, and when present represents a carbonyl group; Y? independently may be present or absent, represents a carbonyl group; Rm which may be the same or different represent 1 to 3 substituents selected from halogen atoms, alkyl groups, and alkoxy groups, or wherein two Rm form together with the carbon atoms of the ring to which they are bonded an annelated aromatic riType: ApplicationFiled: December 4, 2014Publication date: September 8, 2016Applicant: DENTSPLY SIRONA, Inc.Inventors: Joachim E. KLEE, Maximilian MAIER, Christian SCHEUFLER