Patents by Inventor Patrick J. FRYFOGLE
Patrick J. FRYFOGLE 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: 11932775Abstract: A curable coating composition is provided having multi-functionalized acrylic copolymer and silicone imine resin curing agents. The acrylic copolymer of the curable coating composition has, in polymerized form, epoxy functionalized groups and cure compatibility groups and the silicone imine forms an amino-functional silicone in the presence of water. The coating compositions are useful in the field of superior weatherable and durable coatings and are useful to replace isocyanate-containing polyurethane based coatings. Also provided are coated articles produced from the curable composition.Type: GrantFiled: July 17, 2019Date of Patent: March 19, 2024Assignees: Dow Global Technologies LLC, Dow Siliicones CorporationInventors: Alan M. Piwowar, Ray E. Drumright, Erin B. Vogel, Gary M. Wieber, Patrick J. Fryfogle, Yanxiang Li, Susan M. Machelski, Paul J. Popa, Adam C. Tomasik, Gerald Lawrence Witucki
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Patent number: 11834584Abstract: A curable coating composition is provided having multi-functionalized acrylic copolymer and amino-functional silicone resin curing agents. The acrylic copolymer of the curable coating composition has, in polymerized form, epoxy functionalized groups and cure compatibility groups. The coating compositions are useful in the field of superior weatherable and durable coatings and are useful to replace isocyanate-containing polyurethane based coatings. Also provided are coated articles produced from the curable composition.Type: GrantFiled: July 17, 2019Date of Patent: December 5, 2023Assignees: DOW GLOBAL TECHNOLOGIES LLC, Dow Silicones CorporationInventors: Erin B. Vogel, Susan Machelski, Ray E. Drumright, Paul J. Popa, Gary M. Wieber, Gerald Lawrence Witucki, Patrick J. Fryfogle, Adam C. Tomasik
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Patent number: 11753555Abstract: A dispersion contains: (a) a polyorganosiloxane with at least 90 mole % dimethyl D units and viscosity of one kPa*s or more dispersed as 0.5-20 micrometer particles; (b) a condensation product of: (i) a polysiloxane resin (Mw of 4,000-50,000) with composition: (R3SiO1/2)a(SiO4/2)b(ZO1/2)c where a is 0.30-0.60, b is 0.40-0.70, c is 0.05-0.20, a+b is one, R is selected from hydrogen, C1?30 alkyl groups and aryl groups, and Z is selected from H, and C18 alkyls; and (ii) a polyoxyalkylene polymer (Mn of 4,500-50,000) with composition: A—O—(C2H4O)e(C3H6O)p—A? where e/p is 1-9, A and A? are selected from hydrogen, alkyl, substituted alkyl, aryl, and substituted aryl groups and at least one of A and A? is H; (c) non-aqueous fluid carrier miscible with (a); and (d) monoterpene; the weight-ratio of (c) to (b) is 0.5-1; weight-ratio of (b) and (c) to (a) is 0.01-0.50; and the composition contains below one ppm aromatic solvent.Type: GrantFiled: October 11, 2021Date of Patent: September 12, 2023Assignees: DOW SILICONES CORPORATION, ROHM AND HAAS COMPANYInventors: Patrick J. Fryfogle, Julie Cook, Tim Mitchell, Yihan Liu, Rebecca Beeson, Miroslav Janco, Mikayla T. Miller, Brad J. Phillips
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Publication number: 20230242775Abstract: A dispersion contains: (a) a polyorganosiloxane with at least 90 mole % dimethyl D units and viscosity of one kPa*s or more dispersed as 0.5-20 micrometer particles; (b) a condensation product of: (i) a polysiloxane resin (Mw of 4,000-50,000) with composition: (R3SiO1/2)a(SiO4/2)b(ZO1/2)c where a is 0.30-0.60, b is 0.40-0.70, c is 0.05-0.20, a+b is one, R is selected from hydrogen, C1-30 alkyl groups and aryl groups, and Z is selected from H, and C1-8 alkyls; and (ii) a polyoxyalkylene polymer (Mn of 4,500-50,000) with composition: A-O—(C2H4O)e(C3H6O)p-A? where e/p is 1-9, A and A? are selected from hydrogen, alkyl, substituted alkyl, aryl, and substituted aryl groups and at least one of A and A? is H; (c) non-aqueous fluid carrier miscible with (a); and (d) monoterpene; the weight-ratio of (c) to (b) is 0.5-10; weight-ratio of (b) and (c) to (a) is 0.01-0.50; and the composition contains below one ppm aromatic solvent.Type: ApplicationFiled: October 11, 2021Publication date: August 3, 2023Inventors: Patrick J. Fryfogle, Julie Cook, Tim Mitchell, Yihan Liu, Rebecca Beeson, Miroslav Janco, Mikayla T. Miller, Brad J. Phillips
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Patent number: 11267976Abstract: A composition contains a polyorganosiloxane dispersed in a combination of a condensation product of a polysiloxane resin and a polyoxyalkylene polymer, and a non-aqueous fluid carrier; wherein the weight-ratio of non-aqueous fluid carrier to condensation product is 0.5 or more and 10 or less; the weight-ratio of the combination of condensation product and non-aqueous fluid carrier to polyorganosiloxane is 0.01 or more and 0.50 or less; and wherein the composition contains less than one weight-part aromatic solvent per million weight parts composition.Type: GrantFiled: April 16, 2020Date of Patent: March 8, 2022Assignee: Dow Silicones CorporationInventors: Patrick J. Fryfogle, Yihan Liu, Timothy P. Mitchell, Jennifer A. Reil, Michael R. Reiter, John Roberts, Gary M. Wieber, Brett L. Zimmerman
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Publication number: 20220041872Abstract: A composition contains a polyorganosiloxane dispersed in a combination of a condensation product of a polysiloxane resin and a polyoxyalkylene polymer, and a non-aqueous fluid carrier; wherein the weight-ratio of non-aqueous fluid carrier to condensation product is 0.5 or more and 10 or less; the weight-ratio of the combination of condensation product and non-aqueous fluid carrier to polyorganosiloxane is 0.01 or more and 0.50 or less; and wherein the composition contains less than one weight-part aromatic solvent per million weight parts composition.Type: ApplicationFiled: April 16, 2020Publication date: February 10, 2022Inventors: Patrick J. Fryfogle, Yihan Liu, Timothy P. Mitchell, Jennifer A. Reil, Michael R. Reiter, John Roberts, Gary M. Wieber, Brett L. Zimmerman
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Publication number: 20210261818Abstract: A curable coating composition is provided having multi-functionalized acrylic copolymer and silicone imine resin curing agents. The acrylic copolymer of the curable coating composition has, in polymerized form, epoxy functionalized groups and cure compatibility groups and the silicone imine forms an amino-functional silicone in the presence of water. The coating compositions are useful in the field of superior weatherable and durable coatings and are useful to replace isocyanate-containing polyurethane based coatings. Also provided are coated articles produced from the curable composition.Type: ApplicationFiled: July 17, 2019Publication date: August 26, 2021Inventors: Alan M. Piwowar, Ray E. Drumright, Erin B. Vogel, Gary M. Wieber, Patrick J. Fryfogle, Yanxiang Li, Susan M. Machelski, Paul J. Popa, Adam C. Tomasik, Gerald Lawrence Witucki
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Publication number: 20210253900Abstract: A curable coating composition is provided having multi-functionalized acrylic copolymer and amino-functional silicone resin curing agents. The acrylic copolymer of the curable coating composition has, in polymerized form, epoxy functionalized groups and cure compatibility groups. The coating compositions are useful in the field of superior weatherable and durable coatings and are useful to replace isocyanate-containing polyurethane based coatings. Also provided are coated articles produced from the curable composition.Type: ApplicationFiled: July 17, 2019Publication date: August 19, 2021Inventors: Erin B. Vogel, Susan M. Machelski, Ray E. Drumright, Paul J. Popa, Gary M. Wieber, Gerald Lawrence Witucki, Patrick J. Fryfogle, Adam C. Tomasik
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Patent number: 10940099Abstract: The present invention provides methods for preparing emulsions of silicone fluids having pituitous rheological properties. The present invention also provides emulsions of a silicone fluid having pituitous rheological properties and composition comprising the emulsions. The compositions include, but are not limited to, personal care compositions and compositions for hair shampoo, hair conditioner, hair treatment composition, or skin care product.Type: GrantFiled: April 4, 2016Date of Patent: March 9, 2021Assignee: Dow Silicones CorporationInventors: Severine Cauvin, Patrick J. Fryfogle, Sophie Hanssens, Donald Kadlec, Stephane Ugazio, Marine Viaud, Brett Lee Zimmerman
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Publication number: 20200237639Abstract: This invention relates to a cosmetic composition comprising: (A) a film forming composition that can produce a tack free surface comprising: (I) a hydrosilylation reaction product of: (a) a silicone resin having the formula: (R1R22SiO1/2)w(R1R3SiO2/2)x(R1R2SiO3/2)y(SiO4/2)z wherein R2 is a C1 to C10 hydrocarbon group free of aliphatic unsaturation, R1 is R2 or an alkenyl group, w is from 0.3 to 0.6, x is from 0.0 to 0.2, y is 0, z is from 0.4 to 0.7, w+x+y+z=1.0, and w+z is from 0.85 to 1.Type: ApplicationFiled: June 15, 2018Publication date: July 30, 2020Inventors: Thomas D. Bekemeier, Patrick J. Fryfogle, Gary M. Wieber, Kimmai T. Nguyen, Zhi Li, Julie Cook, Jason Vogel
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Publication number: 20200222302Abstract: This invention relates to a film forming composition that can produce a tack free surface comprising: (I) a hydrosilylation reaction product of: (a) a silicone resin having the formula: (R1R22SiO1/2)w(R1R2SiO2/2)x(R2SiO3/2)y(SiO4/2)z wherein R2 is C1 to C10 hydrocarbon group free of aliphatic unsaturation, R1 is R2 or an alkenyl group, w is from 0.3 to 0.6, x is from 0.0 to 0.2, y is 0, z is from 0.4 to 0.7, w+x+y+z=1.0, and w+z is from 0.85 to 1.Type: ApplicationFiled: June 15, 2018Publication date: July 16, 2020Inventors: Thomas D. Bekemeier, Patrick J. Fryfogle, Gary M. Wieber, Kimmai T. Nguyen, Zhi Li, Julie Cook, Jason Vogel
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Patent number: 10500151Abstract: A silicone elastomer composition (“composition”) has customizable sensory characteristics. The composition includes a pituitous silicone fluid that includes a hydrosilylation reaction product and a carrier fluid. The hydrosilylation reaction product generally includes alkenyl or Si—H functionality. The hydrosilylation reaction product is the reaction product of a first linear organopolysiloxane including (R1R2R3SiO—1/2) and (R4R5Si)2/2) units, and a second linear organopolysiloxane including (R6R7R8SiO—1/2) and (R9R10SiO2/2) units. Each of R1-R10 is independently a hydrocarbon group so long as at least one of R1-R5 is an alkenyl group and at least one of R6-R10 is a hydrogen atom. The first linear organopolysiloxane has a DP of from 100 to 15,000. The second linear organopolysiloxane has a DP of from 4 to 1,000. The composition also includes a silicone elastomer different from the hydrosilylation reaction product. Personal care compositions can include the composition.Type: GrantFiled: April 8, 2015Date of Patent: December 10, 2019Assignee: Dow Silicones CorporationInventors: Patrick J. Fryfogle, Donald Anthony Kadlec
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Patent number: 10172781Abstract: A pituitous silicone fluid includes a hydrosilylation reaction product and a carrier fluid. The hydrosilylation reaction product is the reaction product of a first linear organopolysiloxane and a second linear organopolysiloxane. The first linear organopolysiloxane includes (R1R2R3SiO1/2) and (R4R5SiO2/2) units. Each of R1-R5 is independently a hydrocarbon group so long as at least one of R1-R5 is an alkenyl group. In addition, the first linear organopolysiloxane has a degree of polymerization of from 100 to 15,000. The second linear organopolysiloxane includes (R6R7R8SiO1/2) and (R9R10SiO2/2) units. Each of R6-R10 is independently a hydrocarbon group, polyether group, siloxane group, or polyol group, so long as at least one of R6-R10 is a hydrogen atom. In addition, the second linear organopolysiloxane has a degree of polymerization of from 4 to 1,000. The hydrosilylation reaction product includes alkenyl or Si—H functionality. Personal care compositions can include the pituitous silicone fluid.Type: GrantFiled: April 8, 2015Date of Patent: January 8, 2019Assignee: Dow Silicones CorporationInventors: Patrick J. Fryfogle, Donald Anthony Kadlec, Kimmai Thi Nguyen, Ryan Christopher Thomas
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Patent number: 10059806Abstract: An aminosiloxane polymer includes at least one Si-bonded functional group. This functional group has the chemical formula: —(R—NH)aR1—N(R2)—CH(—COOH)(—R3—C(?O)—NR42) (I). In Formula (I), R is a C1-C10 hydrocarbon group. R1 is a C1-C10 hydrocarbon group. R2 is a hydrogen atom, a C1-C12 hydrocarbon group, or a phenyl group. R3 is a C1-C4 hydrocarbon group. Each R4 is independently a hydrogen atom, a C1-C12 hydrocarbon group, a C1-C12 hydroxyl-hydrocarbon group, or a phenyl group. Moreover, “a” is 0 or 1, such that (R—NH) is optional. The aminosiloxane polymer can be formed using the method of this disclosure and can be formed in, and/or included in, the emulsion of this disclosure.Type: GrantFiled: May 20, 2015Date of Patent: August 28, 2018Assignee: Dow Silicones CorporationInventors: Qian Feng, Michael Salvatore Ferritto, Patrick J. Fryfogle, Bethany K. Johnson, Kimmai Thi Nguyen, Brett Lee Zimmerman, Kenneth Edward Zimmerman
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Publication number: 20180078467Abstract: The present invention provides methods for preparing emulsions of silicone fluids having pituitous rheological properties. The present invention also provides emulsions of a silicone fluid having pituitous rheological properties and composition comprising the emulsions. The compositions include, but are not limited to, personal care compositions and compositions for hair shampoo, hair conditioner, hair treatment composition, or skin care product.Type: ApplicationFiled: April 4, 2016Publication date: March 22, 2018Inventors: Severine Cauvin, Patrick J. Fryfogle, Sophie Hanssens, Donald Kadlec, Stephane Ugazio, Marine Vlaud, Brett Lee Zimmerman
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Publication number: 20180064630Abstract: A fluid composition comprises A) a branched organopolysiloxane and B) a carrier fluid. Component A) comprises the reaction product of a) a cyclic siloxane and b) a polyorganosiloxane, in the presence of a hydrosilylation catalyst. Component a) has at least two silicon-bonded alkenyl groups per molecule, and component b) has at least two silicon-bonded hydrogen atoms per molecule. The fluid composition has a viscosity of at least 100 mPa·s at 23° C. and exhibits pituitous rheological properties. The pituitous rheological properties are generally determined from a plot of normal force (in Pascals) vs a perpendicular shear rate in (sec?1). Also disclosed is a personal care composition that comprises the fluid composition. When formulated into a personal care composition, the fluid composition generally provides enhanced sensory and film-forming properties based on its pituitous rheological properties.Type: ApplicationFiled: April 4, 2016Publication date: March 8, 2018Inventors: Patrick J. Fryfogle, Donald Kadlec
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Publication number: 20180066113Abstract: An aminosiloxane polymer includes at least one Si-bonded functional group. This functional group has the chemical formula: —(R—NH)aR1—N(R2)—CH(—COOH)(—R3—C(?O)—NR42) (I). In Formula (I), R is a C1-C10 hydrocarbon group. R1 is a C1-C10 hydrocarbon group. R2 is a hydrogen atom, a C1-C12 hydrocarbon group, or a phenyl group. R3 is a C1-C4 hydrocarbon group. Each R4 is independently a hydrogen atom, a C1-C12 hydrocarbon group, a C1-C12 hydroxyl-hydrocarbon group, or a phenyl group. Moreover, “a” is 0 or 1, such that (R—NH) is optional. The aminosiloxane polymer can be formed using the method of this disclosure and can be formed in, and/or included in, the emulsion of this disclosure.Type: ApplicationFiled: May 20, 2015Publication date: March 8, 2018Inventors: Qian FENG, Michael Salvatore FERRITTO, Patrick J. FRYFOGLE, Bethany K. JOHNSON, Kimmai Thi NGUYEN, Brett Lee ZIMMERMAN, Kenneth Edward ZIMMERMAN
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Patent number: 9890253Abstract: A cross-linked aminosiloxane polymer includes a first siloxane backbone, a second siloxane backbone, and at least one intramolecular structure cross-linking a silicon atom of the first siloxane backbone and a silicon atom of the second siloxane backbone. The intramolecular structure has the chemical structure: (I) In Formula (I), X is chosen from the following groups; (II); (III); or (IV). In groups (II), (III), and (IV), each R is independently a C1-C10 hydrocarbon group. Each R1 is independently a C1-C10 hydrocarbon group. Each R2 is independently a hydrogen atom, OH, a C1-C12 hydrocarbon group, a phenyl group, R?(OR?)m, or R?OH. Each of R? and R? is independently an alkyl group and “m” is 1 to 3. Moreover, “a” is 0 or 1. The cross-linked aminosiloxane polymer can be formed by the method of this disclosure.Type: GrantFiled: May 20, 2015Date of Patent: February 13, 2018Assignee: Dow Corning CorporationInventors: Qian Feng, Patrick J. Fryfogle, Bethany K. Johnson, Zhi Li, Kimmai Thi Nguyen, Ryan Christopher Thomas
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Publication number: 20170360690Abstract: A pituitous silicone fluid includes a hydrosilylation reaction product and a carrier fluid. The hydrosilylation reaction product is the reaction product of a first linear organopolysiloxane and a second linear organopolysiloxane. The first linear organo-polysiloxane includes (R1R2R3SiO1/2) and (R4R5SiO2/2) units. Each of R1-R5 is independently a hydrocarbon group so long as at least one of R1-R5 is an alkenyl group. In addition, the first linear organopolysiloxane has a degree of polymerization of from 100 to 15,000. The second linear organopolysiloxane includes (R6R7R8SiO1/2) and (R9R10SiO2/2) units. Each of R6-R10 is independently a hydrocarbon group, polyether group, siloxane group, or polyol group, so long as at least one of R6-R10 is a hydrogen atom. In addition, the second linear organopolysiloxane has a degree of polymerization of from 4 to 1,000. The hydrosilylation reaction product includes alkenyl or Si—H functionality. Personal care compositions can include the pituitous silicone fluid.Type: ApplicationFiled: April 8, 2015Publication date: December 21, 2017Inventors: Patrick J. FRYFOGLE, Donald Anthony KADLEC, Kimmai Thi NGUYEN, Ryan Christopher THOMAS
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Publication number: 20170355824Abstract: A cross-linked aminosiloxane polymer includes a first siloxane backbone, a second siloxane backbone, and at least one intramolecular structure cross-linking a silicon atom of the first siloxane backbone and a silicon atom of the second siloxane backbone. The intramolecular structure has the chemical structure: (I) In Formula (I), X is chosen from the following groups; (II); (III); or (IV). In groups (II), (III), and (IV), each R is independently a C1-C10 hydrocarbon group. Each R1 is independently a C1-C10 hydrocarbon group. Each R2 is independently a hydrogen atom, OH, a C1-C12 hydrocarbon group, a phenyl group, R?(OR?)m, or R?OH. Each of R? and R? is independently an alkyl group and “m” is 1 to 3. Moreover, “a” is 0 or 1. The cross-linked aminosiloxane polymer can be formed by the method of this disclosure.Type: ApplicationFiled: May 20, 2015Publication date: December 14, 2017Inventors: Qian FENG, Patrick J. FRYFOGLE, Bethany K. JOHNSON, Zhi LI, Kimmai Thi NGUYEN, Ryan Christopher THOMAS