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).
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Patent number: 12084531Abstract: 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: GrantFiled: December 17, 2019Date of Patent: September 10, 2024Assignee: PPG Industries Ohio, Inc.Inventors: Robert D. Herold, Jeremy J. Hay
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Publication number: 20240158554Abstract: 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: ApplicationFiled: March 8, 2022Publication date: May 16, 2024Applicant: PPG Industries Ohio, Inc.Inventors: Marco Antonio Herrera Garcia, Jeremy J. Hay, Kevin H. Klingensmith, Robert D. Herold
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Patent number: 11634537Abstract: 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: GrantFiled: December 18, 2018Date of Patent: April 25, 2023Assignee: Arkema Inc.Inventors: Robert D. Herold, Marco Herrera, Thomas H. Kozel, Leonard H. Palys, Brandy Slezak, Bruno Georges Van Hemelryck
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Publication number: 20220041779Abstract: 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: ApplicationFiled: December 17, 2019Publication date: February 10, 2022Inventors: Robert D. Herold, Jeremy J. Hay
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Patent number: 11028206Abstract: 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: GrantFiled: May 17, 2019Date of Patent: June 8, 2021Assignee: PPG Industries Ohio, Inc.Inventor: Robert D. Herold
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Publication number: 20210070931Abstract: 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: ApplicationFiled: December 18, 2018Publication date: March 11, 2021Inventors: Robert D. HEROLD, Marco HERRERA, Thomas H. KOZEL, Leonard H. PALYS, Brandy SLEZAK, Bruno Georges VAN HEMELRYCK
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Patent number: 10822455Abstract: 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: GrantFiled: August 2, 2019Date of Patent: November 3, 2020Assignee: PPG Industries Ohio, Inc.Inventors: Robert D. Herold, Vivek Badarinarayana
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Publication number: 20190352458Abstract: 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: ApplicationFiled: August 2, 2019Publication date: November 21, 2019Inventors: Robert D. Herold, Vivek Badarinarayana
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Patent number: 10407540Abstract: 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: GrantFiled: September 7, 2016Date of Patent: September 10, 2019Assignee: PPG Industries Ohio, Inc.Inventors: Robert D. Herold, Vivek Badarinarayana
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Publication number: 20190270834Abstract: 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: ApplicationFiled: May 17, 2019Publication date: September 5, 2019Inventor: Robert D. Herold
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Patent number: 10294318Abstract: 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: GrantFiled: August 15, 2017Date of Patent: May 21, 2019Assignee: PPG Industries Ohio, Inc.Inventor: Robert D. Herold
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Publication number: 20180051115Abstract: 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: ApplicationFiled: August 15, 2017Publication date: February 22, 2018Inventor: Robert D. Herold
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Patent number: 9752025Abstract: 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: GrantFiled: November 5, 2013Date of Patent: September 5, 2017Assignee: PPG Industries Ohio, Inc.Inventors: David R. Fenn, Wei Wang, Charles R. Hickenboth, Robert D. Herold
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Publication number: 20170066876Abstract: 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: ApplicationFiled: September 7, 2016Publication date: March 9, 2017Inventors: Robert D. Herold, Vivek Badarinarayana
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Patent number: 9411076Abstract: 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: GrantFiled: September 12, 2013Date of Patent: August 9, 2016Assignee: PPG Industries Ohio, Inc.Inventors: Brandy D. Slezak, Royann L. Stewart-Davis, Robert D. Herold, Mark P. Bowman, Joseph S. Szul
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Patent number: 9334345Abstract: 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: GrantFiled: September 6, 2012Date of Patent: May 10, 2016Assignee: 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
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Publication number: 20140128534Abstract: 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: ApplicationFiled: November 5, 2013Publication date: May 8, 2014Inventors: David R. Fenn, Wei Wang, Charles R. Hickenboth, Robert D. Herold
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Publication number: 20140080972Abstract: 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: ApplicationFiled: September 12, 2013Publication date: March 20, 2014Applicant: PPG INDUSTRIES OHIO, INC.Inventors: Brandy D. Slezak, Royann L. Stewart-Davis, Robert D. Herold, Mark P. Bowman, Joseph S. Szul
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Publication number: 20130082220Abstract: 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: ApplicationFiled: September 6, 2012Publication date: April 4, 2013Applicant: 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
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Patent number: 8017720Abstract: 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: GrantFiled: December 16, 2005Date of Patent: September 13, 2011Assignee: PPG Industries Ohio, Inc.Inventors: Nina V. Bojkova, Robert D. Herold, William H. McDonald, Marvin J. Graham, Robert A. Smith