Patents by Inventor Robert D. Herold

Robert D. Herold 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: 12084531
    Abstract: Compositions including a combination of (meth)acryloyl-terminated monomers and oligomers prepared by co-reacting reactants having active hydrogen groups with an acrylating agent are disclosed. Polymerizates formed using the combinations of (meth)acryloyl-terminated monomers and oligomers exhibit a high hardness, excellent thermomechanical properties, and a high refractive index. The compositions can be used to fabricate optical components.
    Type: Grant
    Filed: December 17, 2019
    Date of Patent: September 10, 2024
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Robert D. Herold, Jeremy J. Hay
  • Publication number: 20240158554
    Abstract: Provided is a polymerizable composition including (a) a polymerizable component comprising a diol bis(allyl carbonate) and/or a pre-polymer thereof; and (b) a polymerization initiator component including: (i) a di(C6-C10 alkyl) peroxydicarbonate, and (ii) an organic peroxide having one peroxy, one peroxycarbonate, or one peroxybenzoate group and a 1,1-dimethylalkyl group bonded to a peroxy oxygen, where (ii) comprises a molecular weight ranging from 200 to 250 g/mole, the polymerization initiator (b) is free of diisopropyl peroxydicarbonate, (i) comprises an amount ranging from 4.87% to 7.90% by weight relative to the total solids of the polymerizable composition and (ii) comprises an amount within the range defined by the following formula: (4.406X2?0.592X+0.021)?Y?(0.726X2?0.121X+0.009) where X corresponds to the weight fraction of (i) and Y corresponds to the weight fraction of (ii). Also provided is a method of making an optical article from the polymerizable composition.
    Type: Application
    Filed: March 8, 2022
    Publication date: May 16, 2024
    Applicant: PPG Industries Ohio, Inc.
    Inventors: Marco Antonio Herrera Garcia, Jeremy J. Hay, Kevin H. Klingensmith, Robert D. Herold
  • Patent number: 11634537
    Abstract: The present invention is directed to a polymerizable composition comprising (A) a reaction product of: (a) diethyleneglycol bischloroformate, ethyleneglycol bischloroformate, or combinations thereof; (b) allyl alcohol; (c) optionally, a cyclic polyol selected from the group consisting of a cycloaliphatic polyol having at least one secondary hydroxyl group, a heterocyclic polyol having primary and/or secondary hydroxyl groups, and mixtures thereof; and (d) optionally, at least one linear or branched aliphatic polyol having two to six hydroxyl groups; and (B) an organic peroxide comprising at least three peroxide groups. A polymerizate and/or an optical article comprising the polymerizable compositions of the invention are also provided.
    Type: Grant
    Filed: December 18, 2018
    Date of Patent: April 25, 2023
    Assignee: Arkema Inc.
    Inventors: Robert D. Herold, Marco Herrera, Thomas H. Kozel, Leonard H. Palys, Brandy Slezak, Bruno Georges Van Hemelryck
  • Publication number: 20220041779
    Abstract: Compositions including a combination of (meth)acryloyl-terminated monomers and oligomers prepared by co-reacting reactants having active hydrogen groups with an acrylating agent are disclosed. Polymerizates formed using the combinations of (meth)acryloyl-terminated monomers and oligomers exhibit a high hardness, excellent thermomechanical properties, and a high refractive index. The compositions can be used to fabricate optical components.
    Type: Application
    Filed: December 17, 2019
    Publication date: February 10, 2022
    Inventors: Robert D. Herold, Jeremy J. Hay
  • Patent number: 11028206
    Abstract: A polymerizable composition includes the reaction product of an isohexide bischloroformate, at least one polyol, allyl alcohol, and, optionally, at least one polychloroformate. An exemplary polymerizable composition includes (a) the transesterification reaction product of an isohexide, diallyl carbonate, and at least one polyol; and (b) organic peroxide. A polymerizate including the polymerizable composition and an optical article including the polymerizable composition are also provided.
    Type: Grant
    Filed: May 17, 2019
    Date of Patent: June 8, 2021
    Assignee: PPG Industries Ohio, Inc.
    Inventor: Robert D. Herold
  • Publication number: 20210070931
    Abstract: The present invention is directed to a polymerizable composition comprising (A) a reaction product of: (a) diethyleneglycol bischloroformate, ethyleneglycol bischloroformate, or combinations thereof; (b) allyl alcohol; (c) optionally, a cyclic polyol selected from the group consisting of a cycloaliphatic polyol having at least one secondary hydroxyl group, a heterocyclic polyol having primary and/or secondary hydroxyl groups, and mixtures thereof; and (d) optionally, at least one linear or branched aliphatic polyol having two to six hydroxyl groups; and (B) an organic peroxide comprising at least three peroxide groups. A polymerizate and/or an optical article comprising the polymerizable compositions of the invention are also provided.
    Type: Application
    Filed: December 18, 2018
    Publication date: March 11, 2021
    Inventors: Robert D. HEROLD, Marco HERRERA, Thomas H. KOZEL, Leonard H. PALYS, Brandy SLEZAK, Bruno Georges VAN HEMELRYCK
  • Patent number: 10822455
    Abstract: An exemplary polymerizable thermosetting composition includes the reaction product of (a) allyl alcohol; (b) a cyclic polyol selected from the group consisting of a cycloaliphatic polyol having at least one secondary hydroxyl group, a heterocyclic polyol having primary and/or secondary hydroxyl groups, and mixtures thereof; (c) ethyleneglycol bischloroformate; and (d) optionally, at least one linear or branched aliphatic polyol having two to six hydroxyl groups. The allyl alcohol (a) is present in an amount of 0.4 to 1.99 equivalents of OH to 1 equivalent chloroformate, and the cyclic polyol (b) is present in an amount of 0.01 to 0.6 equivalents of OH to 1 equivalent of chloroformate. A reaction product, a polymerizate including the polymerizable thermosetting composition, and an optical article including the polymerizable thermosetting composition are also provided.
    Type: Grant
    Filed: August 2, 2019
    Date of Patent: November 3, 2020
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Robert D. Herold, Vivek Badarinarayana
  • Publication number: 20190352458
    Abstract: An exemplary polymerizable thermosetting composition includes the reaction product of (a) allyl alcohol; (b) a cyclic polyol selected from the group consisting of a cycloaliphatic polyol having at least one secondary hydroxyl group, a heterocyclic polyol having primary and/or secondary hydroxyl groups, and mixtures thereof; (c) ethyleneglycol bischloroformate; and (d) optionally, at least one linear or branched aliphatic polyol having two to six hydroxyl groups. The allyl alcohol (a) is present in an amount of 0.4 to 1.99 equivalents of OH to 1 equivalent chloroformate, and the cyclic polyol (b) is present in an amount of 0.01 to 0.6 equivalents of OH to 1 equivalent of chloroformate. A reaction product, a polymerizate including the polymerizable thermosetting composition, and an optical article including the polymerizable thermosetting composition are also provided.
    Type: Application
    Filed: August 2, 2019
    Publication date: November 21, 2019
    Inventors: Robert D. Herold, Vivek Badarinarayana
  • Patent number: 10407540
    Abstract: An exemplary polymerizable composition includes the reaction product of (a) diethyleneglycol bischloroformate; (b) allyl alcohol; (c) a cyclic polyol selected from the group consisting of a cycloaliphatic polyol having at least one secondary hydroxyl group, a heterocyclic polyol having primary and/or secondary hydroxyl groups, and mixtures thereof; (d) optionally, ethyleneglycol bischloroformate; and (e) optionally, at least one linear or branched aliphatic polyol having two to six hydroxyl groups. Another exemplary polymerizable composition includes the reaction product of (a) allyl alcohol; (b) a cyclic polyol selected from the group consisting of a cycloaliphatic polyol having at least one secondary hydroxyl group, a heterocyclic polyol having primary and/or secondary hydroxyl groups, and mixtures thereof; (c) ethyleneglycol bischloroformate; and (d) optionally, at least one linear or branched aliphatic polyol having two to six hydroxyl groups is also described.
    Type: Grant
    Filed: September 7, 2016
    Date of Patent: September 10, 2019
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Robert D. Herold, Vivek Badarinarayana
  • Publication number: 20190270834
    Abstract: A polymerizable composition includes the reaction product of an isohexide bischloroformate, at least one polyol, allyl alcohol, and, optionally, at least one polychloroformate. An exemplary polymerizable composition includes the transesterification reaction product of (a) an isohexide, diallyl carbonate, and at least one polyol; and (b) organic peroxide. A polymerizate including the polymerizable composition and an optical article including the polymerizable composition are also provided.
    Type: Application
    Filed: May 17, 2019
    Publication date: September 5, 2019
    Inventor: Robert D. Herold
  • Patent number: 10294318
    Abstract: A polymerizable composition includes at least one first monomer and at least one second monomer, wherein the at least one first monomer includes an isohexide bis(allyl carbonate) monomer, and wherein the at least one second monomer includes one or more ethylenic unsaturations. Another polymerizable composition includes the reaction product of an isohexide bischloroformate; at least one polyol; allyl alcohol; and, optionally, at least one polychloroformate. An exemplary polymerizable composition includes the transesterification reaction product of an isohexide; diallyl carbonate; and at least one polyol. A polymerizate including the polymerizable composition and an optical article including the polymerizable composition are also provided.
    Type: Grant
    Filed: August 15, 2017
    Date of Patent: May 21, 2019
    Assignee: PPG Industries Ohio, Inc.
    Inventor: Robert D. Herold
  • Publication number: 20180051115
    Abstract: A polymerizable composition includes at least one first monomer and at least one second monomer, wherein the at least one first monomer includes an isohexide bis(allyl carbonate) monomer, and wherein the at least one second monomer includes one or more ethylenic unsaturations. Another polymerizable composition includes the reaction product of an isohexide bischloroformate; at least one polyol; allyl alcohol; and, optionally, at least one polychloroformate. An exemplary polymerizable composition includes the transesterification reaction product of an isohexide; diallyl carbonate; and at least one polyol. A polymerizate including the polymerizable composition and an optical article including the polymerizable composition are also provided.
    Type: Application
    Filed: August 15, 2017
    Publication date: February 22, 2018
    Inventor: Robert D. Herold
  • Patent number: 9752025
    Abstract: Provided is a polymerizable non-aqueous dispersion, wherein the non-aqueous dispersion comprises: (a) a polymerizable component; and (b) polymeric microparticles dispersed in a continuous phase, wherein the microparticles comprise a dispersion polymerization reaction product prepared from a reaction mixture comprising an ethylenically unsaturated monomer, and an acrylic polymer stabilizer, and wherein the continuous phase is the same as or different from the polymerizable component (a). Also provided are optical articles prepared from the polymerizable non-aqueous dispersions.
    Type: Grant
    Filed: November 5, 2013
    Date of Patent: September 5, 2017
    Assignee: PPG Industries Ohio, Inc.
    Inventors: David R. Fenn, Wei Wang, Charles R. Hickenboth, Robert D. Herold
  • Publication number: 20170066876
    Abstract: An exemplary polymerizable composition includes the reaction product of (a) diethyleneglycol bischloroformate; (b) allyl alcohol; (c) a cyclic polyol selected from the group consisting of a cycloaliphatic polyol having at least one secondary hydroxyl group, a heterocyclic polyol having primary and/or secondary hydroxyl groups, and mixtures thereof; (d) optionally, ethyleneglycol bischloroformate; and (e) optionally, at least one linear or branched aliphatic polyol having two to six hydroxyl groups. Another exemplary polymerizable composition includes the reaction product of (a) allyl alcohol; (b) a cyclic polyol selected from the group consisting of a cycloaliphatic polyol having at least one secondary hydroxyl group, a heterocyclic polyol having primary and/or secondary hydroxyl groups, and mixtures thereof; (c) ethyleneglycol bischloroformate; and (d) optionally, at least one linear or branched aliphatic polyol having two to six hydroxyl groups is also described.
    Type: Application
    Filed: September 7, 2016
    Publication date: March 9, 2017
    Inventors: Robert D. Herold, Vivek Badarinarayana
  • Patent number: 9411076
    Abstract: Provided is a polymerizable composition including: (a) a polymerizable component; and (b) a pigment component the pigment component includes: (i) an ionic or amphoteric dispersant material; and (ii) pigment nanoparticles uniformly dispersed in the dispersant material (i). The nanoparticles have a particle size of up to 500 nanometers. Also provided is a polymerizable composition of: (a) a polymerizable component including: (i) diethylene glycol bis(allyl carbonate); and (ii) a radical initiator; and (b) a pigment component which includes: (i) an ionic or amphoteric dispersant material derived from polycaprolactone; and (ii) pigment nanoparticles of ultramarine blue having an average particle size of up to 500 nanometers, uniformly dispersed in the dispersant material.
    Type: Grant
    Filed: September 12, 2013
    Date of Patent: August 9, 2016
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Brandy D. Slezak, Royann L. Stewart-Davis, Robert D. Herold, Mark P. Bowman, Joseph S. Szul
  • Patent number: 9334345
    Abstract: Provided is a polymerizable composition including (meth)acrylate monomers having at least two sulfide (—S—) linkages in the monomer. The polymerizable compositions include a first (meth)acrylate monomer represented by the following Formula (I), where L1 is selected from a multivalent optionally substituted hydrocarbyl group optionally interrupted with at least one of —C(O)—, —S—, —O— and combinations thereof, and a divalent linking group represented by the following Formula (A). In Formula (A), Y is O or S. Also in Formula (I), L2 is independently for each n a divalent optionally substituted hydrocarbyl group optionally interrupted with at least one of —O— and —S—, R1 is independently selected for each n from hydrogen and methyl, and n is from 2 to 6. The polymerizable compositions also may include a polymerization moderator. Also provided are polymerizates including photochromic articles and optical elements prepared from such polymerizable compositions.
    Type: Grant
    Filed: September 6, 2012
    Date of Patent: May 10, 2016
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Robert D. Herold, Nina V. Bojkova, Marvin J. Graham, Charles R. Hickenboth, Gregory J. McCollum, William H. Retsch, Jr., Hongying Zhou
  • Publication number: 20140128534
    Abstract: Provided is a polymerizable non-aqueous dispersion, wherein the non-aqueous dispersion comprises: (a) a polymerizable component; and (b) polymeric microparticles dispersed in a continuous phase, wherein the microparticles comprise a dispersion polymerization reaction product prepared from a reaction mixture comprising an ethylenically unsaturated monomer, and an acrylic polymer stabilizer, and wherein the continuous phase is the same as or different from the polymerizable component (a). Also provided are optical articles prepared from the polymerizable non-aqueous dispersions.
    Type: Application
    Filed: November 5, 2013
    Publication date: May 8, 2014
    Inventors: David R. Fenn, Wei Wang, Charles R. Hickenboth, Robert D. Herold
  • Publication number: 20140080972
    Abstract: Provided is a polymerizable composition including: (a) a polymerizable component; and (b) a pigment component the pigment component includes: (i) an ionic or amphoteric dispersant material; and (ii) pigment nanoparticles uniformly dispersed in the dispersant material (i). The nanoparticles have a particle size of up to 500 nanometers. Also provided is a polymerizable composition of: (a) a polymerizable component including: (i) diethylene glycol bis(allyl carbonate); and (ii) a radical initiator; and (b) a pigment component which includes: (i) an ionic or amphoteric dispersant material derived from polycaprolactone; and (ii) pigment nanoparticles of ultramarine blue having an average particle size of up to 500 nanometers, uniformly dispersed in the dispersant material.
    Type: Application
    Filed: September 12, 2013
    Publication date: March 20, 2014
    Applicant: PPG INDUSTRIES OHIO, INC.
    Inventors: Brandy D. Slezak, Royann L. Stewart-Davis, Robert D. Herold, Mark P. Bowman, Joseph S. Szul
  • Publication number: 20130082220
    Abstract: Provided is a polymerizable composition including (meth)acrylate monomers having at least two sulfide (—S—) linkages in the monomer. The polymerizable compositions include a first (meth)acrylate monomer represented by the following Formula (I), where L1 is selected from a multivalent optionally substituted hydrocarbyl group optionally interrupted with at least one of —C(O)—, —S—, —O— and combinations thereof, and a divalent linking group represented by the following Formula (A). In Formula (A), Y is O or S. Also in Formula (I), L2 is independently for each n a divalent optionally substituted hydrocarbyl group optionally interrupted with at least one of —O— and —S—, R1 is independently selected for each n from hydrogen and methyl, and n is from 2 to 6. The polymerizable compositions also may include a polymerization moderator. Also provided are polymerizates including photochromic articles and optical elements prepared from such polymerizable compositions.
    Type: Application
    Filed: September 6, 2012
    Publication date: April 4, 2013
    Applicant: PPG INDUSTRIES OHIO, INC.
    Inventors: Robert D. Herold, Nina V. Bojkova, Marvin J. Graham, Charles R. Hickenboth, Gregory J. McCollum, William H. Retsch, JR., Hongying Zhou
  • Patent number: 8017720
    Abstract: The present invention provides polythiol oligomer formed by the reaction of at least two or more different dienes and at least one or more dithiol wherein stoichiometric ratio of the sum of the number of equivalents of all polythiols to the sum of the number of equivalents of all dienes used to form the polythiol oligomer is greater than 1.0:1.0; and wherein the two or more different dienes comprise (a) at least one non-cyclic diene and at least one cyclic diene; or (b) at least one aromatic ring-containing diene and at least one non-aromatic cyclic diene; or (c) at least one non-aromatic monocyclic diene and at least one non-aromatic polycyclic diene; Sulfur-containing polyurethane of the present invention can be prepared by combining polyisocyanate, polyisothiocyanate, or mixture thereof; the polythiol oligomer described above; and active hydrogen-containing material.
    Type: Grant
    Filed: December 16, 2005
    Date of Patent: September 13, 2011
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Nina V. Bojkova, Robert D. Herold, William H. McDonald, Marvin J. Graham, Robert A. Smith