Patents by Inventor Robert S. Clough

Robert S. Clough 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).

  • Patent number: 11945900
    Abstract: The present disclosure provides an orthodontic article including the reaction product of the polymerizable composition. Further, the present disclosure provides polymerizable compositions and methods of making an orthodontic article. The method includes obtaining a polymerizable composition and selectively curing the polymerizable composition to form an orthodontic article. Further, methods are provided, including receiving, by a manufacturing device having one or more processors, a digital object comprising data specifying an orthodontic article; and generating, with the manufacturing device by an additive manufacturing process, the orthodontic article based on the digital object. A system is also provided, including a display that displays a 3D model of an orthodontic article; and one or more processors that, in response to the 3D model selected by a user, cause a 3D printer to create a physical object of an orthodontic article.
    Type: Grant
    Filed: June 27, 2019
    Date of Patent: April 2, 2024
    Assignee: 3M Innovative Properties Company
    Inventors: Thomas P. Klun, Zeba Parkar, John M. Riedesel, Richard J. Pokorny, Chad M. Amb, Benjamin R. Coonce, Robert S. Clough, Tianyu Wu, Saswata Chakraborty, Yongshang Lu, Benjamin C. MacMurray, Ahmed S. Abuelyaman, Karl J. L. Geisler, Jodi L. Connell, Ta-Hua Yu
  • Patent number: 11904031
    Abstract: An orthodontic article is described comprising the reaction product of a free-radically polymerizable resin; a first free-radical photoinitiator having sufficient absorbance at a first wavelength range; and a second free-radical initiator selected from a second photoinitiator having sufficient absorbance at a second wavelength range, wherein the second wavelength range is different than the first wavelength range, or a thermal free-radical initiator. In some embodiments, the first free-radical photoinitiator exhibits a maximum absorbance at a wavelength of the range of 370-380 nm or 320-330 nm and/or comprises photoinitiator groups selected from acyl phosphine oxide or alkyl amine acetophenone. Also described are photopolymerizable compositions and methods.
    Type: Grant
    Filed: November 20, 2018
    Date of Patent: February 20, 2024
    Assignee: 3M Innovative Properties Company
    Inventors: Saswata Chakraborty, Benjamin C. MacMurray, Eric W. Nelson, Thomas P. Klun, Richard J. Pokorny, Wayne S. Mahoney, Chad M. Amb, George W. Griesgraber, Dana R. Reed, Ahmed S. Abuelyaman, Robert S. Clough, James D. Hansen, Daniel J. Skamser, Ian Dailey, John M. Riedesel
  • Patent number: 11787929
    Abstract: A composition is described comprising semicrystalline polylactic acid polymer; polyvinyl acetate polymer having a glass transition temperature (Tg) of at least 25° C.; plasticizer; and optionally amorphous polylactic acid polymer. In another embodiment the composition further comprises nucleating agent. Also described are films comprising the composition as well as articles, such as a tape or sheet, comprising the film described herein and a layer of pressure sensitive adhesive disposed on the film.
    Type: Grant
    Filed: January 7, 2022
    Date of Patent: October 17, 2023
    Assignee: 3M Innovative Properties Company
    Inventors: Ning Zhou, Robert S. Clough, Derek J. Dehn, Jeffrey P. Kalish, William W. Merrill, Kevin M. Lewandowski, Jayant Chakravarty
  • Publication number: 20230322966
    Abstract: The present disclosure provides a photopolymerizable composition. The photopolymerizable composition includes a) 40-60 parts by weight of a monofunctional (meth)acrylate monomer, per 100 parts of the total photopolymerizable composition; b) a photoinitiator; and c) a polymerization reaction product of components. A cured homopolymer of the monofunctional (meth)acrylate monomer has a glass transition temperature of 125 degrees Celsius or greater. The polymerization reaction product of components includes i) a diisocyanate; ii) a hydroxy functional methacrylate; iii) a polycarbonate diol; and iv) a catalyst. The polymerization reaction product includes a polyurethane methacrylate polymer.
    Type: Application
    Filed: May 31, 2023
    Publication date: October 12, 2023
    Inventors: Thomas P. Klun, Zeba Parkar, John M. Riedesel, Richard J. Pokorny, Chad M. Amb, Benjamin R. Coonce, Robert S. Clough, Tianyu Wu, Saswata Chakraborty, Yongshang Lu, Benjamin C. Mac Murray
  • Patent number: 11752749
    Abstract: A composite article includes a multilayer barrier assembly bonded to a substrate, and a top polymer layer bonded to the multilayer barrier assembly opposite the substrate. The multilayer barrier assembly comprises a base polymer layer and a base inorganic barrier layer. The base polymer layer comprises a polymerized reaction product of polymerizable components comprising at least one di(meth)acrylate represented by the formula Each R1 independently represents H or methyl; each R2 independently represents an alkyl group having from 1 to 4 carbon atoms; x=0, 1, 2, 3, or 4; and z=0, 1, 2, 3, or 4, with the provisos that at least one of x and z is not zero and 1?x+z?4. Methods of making the same are also disclosed.
    Type: Grant
    Filed: April 16, 2021
    Date of Patent: September 12, 2023
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Robert S. Clough, Joseph C. Spagnola, Christopher S. Lyons, Mark D. Weigel, Thomas P. Klun
  • Patent number: 11708428
    Abstract: The present disclosure provides a photopolymerizable composition. The photopolymerizable composition includes a) 40-60 parts by weight of a monofunctional (meth)acrylate monomer, per 100 parts of the total photopolymerizable composition; b) a photoinitiator; and c) a polymerization reaction product of components. A cured homopolymer of the monofunctional (meth)acrylate monomer has a glass transition temperature of 125 degrees Celsius or greater. The polymerization reaction product of components includes i) a diisocyanate; ii) a hydroxy functional methacrylate; iii) a polycarbonate diol; and iv) a catalyst. The polymerization reaction product includes a polyurethane methacrylate polymer. Often, the polyurethane methacrylate polymer has a weight average molecular weight of 8,000 g/mol or greater. The present disclosure further provides an article and methods thereof.
    Type: Grant
    Filed: June 10, 2021
    Date of Patent: July 25, 2023
    Assignee: 3M Innovative Properties Company
    Inventors: Thomas P. Klun, Zeba Parkar, John M. Riedesel, Richard J. Pokorny, Chad M. Amb, Benjamin R. Coonce, Robert S. Clough, Tianyu Wu, Saswata Chakraborty, Yongshang Lu, Benjamin C. MacMurray
  • Publication number: 20230159680
    Abstract: Orthodontic articles and polymerizable resin compositions are described. The orthodontic article comprises a cured composition comprising the reaction product of free-radically polymerizable resin comprising 30 to 70 wt. %, inclusive, of at least one urethane component, and 25 to 70 wt. %, inclusive, of reactive diluent(s) comprising at least one monofunctional (meth)acrylate monomer. The polymerizable resin comprises no greater than 35 wt. % of reactive diluent(s) having a high affinity for water. Reactive diluent(s) such as monofunctional (meth)acrylate monomers having a high affinity for water have low log P values. In one embodiment, the polymerizable resin comprises at least one acidic monomer.
    Type: Application
    Filed: January 6, 2023
    Publication date: May 25, 2023
    Inventors: Tianyu Wu, Saswata Chakraborty, Benjamin C. MacMurray, Richard J. Pokorny, Thomas P. Klun, Wayne S. Mahoney, Chad M. Amb, Ahmed Abuelyaman, Robert S. Clough, John M. Riedesel, James D. Hansen, Ian Dailey, Daniel J. Skamser, Eric W. Nelson, George W. Griesgraber, Dana R. Reed
  • Patent number: 11584817
    Abstract: Orthodontic articles and polymerizable resin compositions are described. The orthodontic article comprises a cured composition comprising the reaction product of free-radically polymerizable resin comprising 30 to 70 wt. %, inclusive, of at least one urethane component, and 25 to 70 wt. %, inclusive, of reactive diluent(s) comprising at least one monofunctional (meth)acrylate monomer. The polymerizable resin comprises no greater than 35 wt. % of reactive diluent(s) having a high affinity for water. Reactive diluent(s) such as monofunctional (meth)acrylate monomers having a high affinity for water have low log P values. In one embodiment, the polymerizable resin comprises at least one acidic monomer.
    Type: Grant
    Filed: June 26, 2019
    Date of Patent: February 21, 2023
    Assignee: 3M Innovative Properties Company
    Inventors: Tianyu Wu, Saswata Chakraborty, Benjamin C. MacMurray, Richard J. Pokorny, Thomas P. Klun, Wayne S. Mahoney, Chad M. Amb, Ahmed S. Abuelyaman, Robert S. Clough, John M. Riedesel, James D. Hansen, Ian Dailey, Daniel J. Skamser, Eric W. Nelson, George W. Griesgraber, Dana R. Reed
  • Patent number: 11584113
    Abstract: A composite article includes a multilayer barrier assembly bonded to a substrate, and a top polymer layer bonded to the multilayer barrier assembly opposite the substrate. The multilayer barrier assembly comprises a base polymer layer and a base inorganic barrier layer. The base polymer layer comprises a polymerized reaction product of polymerizable components comprising at least one di(meth)acrylate represented by the formula: Formula (I) Each R1 independently represents H or methyl; each R2 independently represents an alkyl group having from 1 to 4 carbon atoms; x=0, 1, 2, 3, or 4; and z=0, 1, 2, 3, or 4, with the provisos that at least one of x and z is not zero and 1?x+z?4. Methods of making the same are also disclosed.
    Type: Grant
    Filed: August 18, 2016
    Date of Patent: February 21, 2023
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Robert S. Clough, Joseph C. Spagnola, Christopher S. Lyons, Mark D. Weigel, Thomas P. Klun
  • Publication number: 20220127444
    Abstract: A composition is described comprising semicrystalline polylactic acid polymer; polyvinyl acetate polymer having a glass transition temperature (Tg) of at least 25° C.; plasticizer; and optionally amorphous polylactic acid polymer. In another embodiment the composition further comprises nucleating agent. Also described are films comprising the composition as well as articles, such as a tape or sheet, comprising the film described herein and a layer of pressure sensitive adhesive disposed on the film.
    Type: Application
    Filed: January 7, 2022
    Publication date: April 28, 2022
    Inventors: Ning Zhou, Robert S. Clough, Derek J. Dehn, Jeffrey P. Kalish, William W. Merrill, Kevin M. Lewandowski, Jayant Chakravarty
  • Publication number: 20220056258
    Abstract: In one embodiment, an orthodontic article is described comprising the reaction product of a polymerizable composition comprising: a) 30-70 parts by weight of monofunctional (meth)acrylate monomer, wherein a cured homopolymer of at least one monofunctional (meth)acrylate monomer has a Tg of at least 30, 35, 40, 45, 50, 55, or 60° C.; and b) urethane (meth)acrylate polymer comprising polymerized units of an aliphatic polyester diol. Also described are polymerizable compositions, as well as methods and systems for making an article utilizing 3D printing.
    Type: Application
    Filed: October 31, 2019
    Publication date: February 24, 2022
    Inventors: Thomas P. Klun, Richard J. Pokorny, Chad M. Amb, Benjamin R. Coonce, Tianyu Wu, Saswata Chakraborty, Yongshang Lu, Benjamin C. Mac Murray, Robert S. Clough, Ahmed S. Abuelyaman, John M. Riedesel
  • Patent number: 11254812
    Abstract: A composition is described comprising semicrystalline polylactic acid polymer; polyvinyl acetate polymer having a glass transition temperature (Tg) of at least 25° C.; plasticizer; and optionally amorphous polylactic acid polymer. In another embodiment the composition further comprises nucleating agent. Also described are films comprising the composition as well as articles, such as a tape or sheet, comprising the film described herein and a layer of pressure sensitive adhesive disposed on the film.
    Type: Grant
    Filed: January 21, 2020
    Date of Patent: February 22, 2022
    Assignee: 3M Innovative Properties Company
    Inventors: Ning Zhou, Robert S. Clough, Derek J. Dehn, Jeffrey P. Kalish, William W. Merrill, Kevin M. Lewandowski, Jayant Chakravarty
  • Patent number: 11225535
    Abstract: The present disclosure provides a photopolymerizable composition. The photopolymerizable composition includes a) 40-60 parts by weight of a monofunctional (meth)acrylate monomer, per 100 parts of the total photopolymerizable composition; b) a photoinitiator; and c) a polymerization reaction product of components. A cured homopolymer of the monofunctional (meth)acrylate monomer has a glass transition temperature of 125 degrees Celsius or greater. The polymerization reaction product of components includes i) a diisocyanate; ii) a hydroxy functional methacrylate; iii) a polycarbonate diol; and iv) a catalyst. The polymerization reaction product includes a polyurethane methacrylate polymer.
    Type: Grant
    Filed: May 21, 2019
    Date of Patent: January 18, 2022
    Assignee: 3M Innovative Properties Company
    Inventors: Thomas P. Klun, Zeba Parkar, John M. Riedesel, Richard J. Pokorny, Chad M. Amb, Benjamin R. Coonce, Robert S. Clough, Tianyu Wu, Saswata Chakraborty, Yongshang Lu, Benjamin C. MacMurray, Ian Dailey, David B. Olson
  • Publication number: 20210386522
    Abstract: An orthodontic article is described comprising a cured composition comprising the reaction product of free-radically polymerizable resin comprising at least one monomer, oligomer and/or polymer, comprising at least two (meth)acryl moieties; a monofunctional reactive diluent; and a polymer or macromolecule comprising a free-radical photoinitiator group. The polymer or macromolecule has a molecular weight of at least 500 g/mole. In one embodiment, the cured composition comprises a first and second photoinitiator wherein at least one is a polymer or macromolecule. Also described are photopolymerizable compositions and methods.
    Type: Application
    Filed: November 20, 2018
    Publication date: December 16, 2021
    Inventors: Saswata Chakraborty, Benjamin C. Mac Murray, Eric W. Nelson, Thomas P. Klun, Wayne S. Mahoney, Chad M. Amb, George W. Griesgraber, Dana R. Reed, Ahmed S. Abuelyaman, Robert S. Clough, James D. Hansen, Daniel J. Skamser, Ian Dailey, John M. Riedesel
  • Patent number: 11198757
    Abstract: A composition includes a photolatent amine, camphorquinone, and a coumarin sensitizer. The coumarin sensitizer is triplet photosensitizer and has an absorbance with a wavelength of maximum absorbance in a range from 390 nanometers to 510 nanometers. Compositions that further include a polymerizable material are also disclosed. Polymer networks preparable from such compositions and methods for making the polymer networks are also disclosed.
    Type: Grant
    Filed: November 2, 2017
    Date of Patent: December 14, 2021
    Assignee: 3M Innovative Properties Company
    Inventors: Robert S. Clough, Sheng Ye, Tao Gong, Jonathan D. Zook, Susan E. DeMoss, Charlie P. Blackwell
  • Publication number: 20210301042
    Abstract: The present disclosure provides a photopolymerizable composition. The photopolymerizable composition includes a) 40-60 parts by weight of a monofunctional (meth)acrylate monomer, per 100 parts of the total photopolymerizable composition; b) a photoinitiator; and c) a polymerization reaction product of components. A cured homopolymer of the monofunctional (meth)acrylate monomer has a glass transition temperature of 125 degrees Celsius or greater. The polymerization reaction product of components includes i) a diisocyanate; ii) a hydroxy functional methacrylate; iii) a polycarbonate diol; and iv) a catalyst. The polymerization reaction product includes a polyurethane methacrylate polymer.
    Type: Application
    Filed: June 10, 2021
    Publication date: September 30, 2021
    Inventors: Thomas P. Klun, Zeba Parkar, John M. Riedesel, Richard J. Pokorny, Chad M. Amb, Benjamin R. Coonce, Robert S. Clough, Tianyu Wu, Saswata Chakraborty, Yongshang Lu, Benjamin C. Mac Murray
  • Publication number: 20210268782
    Abstract: A composite article includes a multilayer barrier assembly bonded to a substrate, and a top polymer layer bonded to the multilayer barrier assembly opposite the substrate. The multilayer barrier assembly comprises a base polymer layer and a base inorganic barrier layer. The base polymer layer comprises a polymerized reaction product of polymerizable components comprising at least one di(meth)acrylate represented by the formula Each R1 independently represents H or methyl; each R2 independently represents an alkyl group having from 1 to 4 carbon atoms; x=0, 1, 2, 3, or 4; and z=0, 1, 2, 3, or 4, with the provisos that at least one of x and z is not zero and 1?x+z?4. Methods of making the same are also disclosed.
    Type: Application
    Filed: April 16, 2021
    Publication date: September 2, 2021
    Inventors: Robert S. Clough, Joseph C. Spagnola, Christopher S. Lyons, Mark D. Weigel, Thomas P. Klun
  • Patent number: 11104758
    Abstract: The present disclosure provides an orthodontic article including the reaction product of the photopolymerizable composition. The photopolymerizable composition includes i) a monofunctional (meth)acrylate monomer whose cured homopolymer has a glass transition temperature of 90 degrees Celsius or greater; ii) a photoinitiator; and iii) a polymerization reaction product of components. The components include 1) an isocyanate; 2) a (meth)acrylate mono-ol; 3) a polycarbonate diol; and 4) a catalyst. Further, the present disclosure provides a method of making an orthodontic article. The method includes obtaining a photopolymerizable composition and selectively curing the photopolymerizable composition to form an orthodontic article.
    Type: Grant
    Filed: May 21, 2019
    Date of Patent: August 31, 2021
    Assignee: 3M Innovative Properties Company
    Inventors: Thomas P. Klun, Zeba Parkar, John M. Riedesel, Richard J. Pokorny, Chad M. Amb, Benjamin R. Coonce, Robert S. Clough, Tianyu Wu, Saswata Chakraborty, Yongshang Lu, Benjamin C. MacMurray, Ian Dailey, David B. Olson
  • Publication number: 20210238328
    Abstract: Orthodontic articles and polymerizable resin compositions are described. The orthodontic article comprises a cured composition comprising the reaction product of free-radically polymerizable resin comprising 30 to 70 wt. %, inclusive, of at least one urethane component, and 25 to 70 wt. %, inclusive, of reactive diluent(s) comprising at least one monofunctional (meth)acrylate monomer. The polymerizable resin comprises no greater than 35 wt. % of reactive diluent(s) having a high affinity for water. Reactive diluent(s) such as monofunctional (meth)acrylate monomers having a high affinity for water have low log P values. In one embodiment, the polymerizable resin comprises at least one acidic monomer.
    Type: Application
    Filed: June 26, 2019
    Publication date: August 5, 2021
    Inventors: Tianyu Wu, Saswata Chakraborty, Benjamin C. Mac Murray, Richard J. Pokorny, Thomas P. Klun, Wayne S. Mahoney, Chad M. Amb, Ahmed S. Abuelyaman, Robert S. Clough, John M. Riedesel, James D. Hansen, Ian Dailey, Daniel J. Skamser, Eric W. Nelson, George W. Griesgraber, Dana R. Reed
  • Publication number: 20210186820
    Abstract: An orthodontic article is described comprising the reaction product of a free-radically polymerizable resin; a first free-radical photoinitiator having sufficient absorbance at a first wavelength range; and a second free-radical initiator selected from a second photoinitiator having sufficient absorbance at a second wavelength range, wherein the second wavelength range is different than the first wavelength range, or a thermal free-radical initiator. In some embodiments, a 1 g/liter acetonitrile solution, at a pathlength of 1 cm, has an absorbance of greater than 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, or 0.10 at a wavelength of the first wavelength range when measured with a spectrophotometer. In some embodiments, the first free-radical photoinitiator exhibits a maximum absorbance at a wavelength of the range of 370-380 nm or 320-330 nm and/or comprises photoinitiator groups selected from acyl phosphine oxide or alkyl amine acetophenone.
    Type: Application
    Filed: November 20, 2018
    Publication date: June 24, 2021
    Inventors: Saswata Chakraborty, Benjamin C. Mac Murray, Eric W. Nelson, Thomas P. Klun, Richard J. Pokorny, Wayne S. Mahoney, Chad M. Amb, George W. Griesgraber, Dana R. Reed, Ahmed S. Abuelyaman, Robert S. Clough, James D. Hansen, Daniel J. Skamser, Ian Dailey, John M. Riedesel