Patents by Inventor Axel Hans-Joachim Herzog
Axel Hans-Joachim Herzog 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: 8865843Abstract: The present disclosure is directed to a sag control agent comprising a reaction product of an isocyanate and a fluorinated amine. This disclosure is further directed to a coating composition comprising the sag control agent. This disclosure is also directed to a process of forming a sag-free coating layer on a substrate.Type: GrantFiled: September 16, 2010Date of Patent: October 21, 2014Assignee: Axalta Coating Systems IP Co., LLCInventors: Rajesh Gopalan Saliya, Ayumu Yokoyama, Sheau-Hwa Ma, Axel Hans-Joachim Herzog
-
Patent number: 8501952Abstract: The present invention is directed to a fluorosilane represented by (L)3-Si—(CH2)n—N(-Q3-Rf)-Q1-Rf where each n is independently an integer from 1 to 12; L is independently chosen from a hydrolysable or non-hydrolysable monovalent group Rf is chosen from a C2-C12 perfluoroalkyl provided that: i) one fluorine atom of the perfluoroalkyl can be optionally replaced by hydrogen, and/or ii) the perfluoroalkyl can be optionally interrupted by at least one oxygen, methylene, or ethylene; Q1 is chosen from the group consisting of a C2-C12 hydrocarbylene optionally interrupted by at least one divalent organic group; X1 is chosen from O or S; and b) Q1 and Q3 are independently chosen from the group consisting of a C2-C12 hydrocarbylene interrupted by at least one of —C(O)—O— or —O—C(O)—, and optionally further interrupted by at least one divalent organic group.Type: GrantFiled: September 23, 2011Date of Patent: August 6, 2013Assignee: E. I. du Pont de Nemours and CompanyInventors: Axel Hans-Joachim Herzog, Gerald Oronde Brown
-
Patent number: 8420826Abstract: The present invention is directed to a fluorosilane represented by (L)3-Si—(CH2)n—(Z1)a—[C(X1)]x—(Z2)l-Q1-Rf where each n is independently an integer from 1 to 12; L is independently chosen from a hydrolysable or non-hydrolysable monovalent group; Rf is chosen from a C2-C12 perfluoroalkyl provided that: i) one fluorine atom of the perfluoroalkyl can be optionally replaced by hydrogen, and/or ii) the perfluoroalkyl can be optionally interrupted by at least one oxygen, methylene, or ethylene; Q1 is chosen from the group consisting of a C2-C12 hydrocarbylene optionally interrupted by at least one divalent organic group; X1 is chosen from O or S; —Z2 is —NH— and Z1 is from the group consisting of —O—, and —S—; each R1 is independently chosen from hydrogen, phenyl, or a monovalent C1-C8 alkyl optionally terminated by —C6H5, preferably H or CH3.Type: GrantFiled: September 23, 2011Date of Patent: April 16, 2013Assignee: E. I. du Pont de Nemours and CompanyInventors: Axel Hans-Joachim Herzog, Gerald Oronde Brown
-
Publication number: 20120171478Abstract: The present disclosure is directed to a sag control agent comprising a reaction product of an isocyanate and a fluorinated amine. This disclosure is further directed to a coating composition comprising the sag control agent. This disclosure is also directed to a process of forming a sag-free coating layer on a substrate.Type: ApplicationFiled: September 16, 2010Publication date: July 5, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Rajesh Gopalan Saliya, Ayumu Yokoyama, Sheau-Hwa Ma, Axel Hans-Joachim Herzog
-
Patent number: 8153834Abstract: The present invention relates to particles, i.e., oxides of Si, Ti, Zn, Zr, Mn, Al and combinations thereof, where at least one particle has a surface covalently bonded to at least one fluorosilane group. The particle is first bonded to a divalent organic linking group which in turn is bonded to a perfluoroalkyl group. It has been discovered that incorporation of the aforementioned divalent organic linking group can improve the ability of the resulting hydrophobized inorganic particles to impart hydrophobic and oleophobic properties.Type: GrantFiled: December 4, 2008Date of Patent: April 10, 2012Assignee: E.I. duPont de Nemours and CompanyInventors: Gerald Oronde Brown, Axel Hans-Joachim Herzog
-
Patent number: 8153846Abstract: The present invention provides a method of making sulfur containing fluoroalkyl amines which overcomes the problems of previously known methods. Sulfur containing fluoroalkyl amines are useful as intermediates for compounds which are in turn useful for imparting water and oil repellency to textiles. Sulfur containing fluoroalkyl amines used in this manner may be found in Example 8 of Rondestvedt et al. (U.S. Pat. No. 3,655,732) wherein they are made by reacting an iodo-fluoroalkyl with an aminoalkyl thiol. Specifically, Rondestvedt et al. teaches reacting CF3(CF2)5(CH2)2I (an iodo-fluoroalkyl) with HS—CH2CH2—NH2 (an aminoalkyl thiol) to make CF3(CF2)5(CH2)2—S—CH2CH2—NH2 (a sulfur containing fluoroalkyl amine). Unlike previously known methods, the method of the present invention can achieve higher yields of sulfur containing fluoroalkyl amines without resorting to costly solvents.Type: GrantFiled: November 18, 2008Date of Patent: April 10, 2012Assignee: E.I. du Pont de Nemours and CompanyInventors: Axel Hans-Joachim Herzog, Hollis Thomas Warren, Brent Ryan Gonska
-
Publication number: 20120022266Abstract: The present invention is directed to a fluorosilane represented by (L)3-Si—(CH2)n—(Z1)a—[C(X1)]x—(Z2)l-Q1-Rf where each n is independently an integer from 1 to 12; L is independently chosen from a hydrolysable or non-hydrolysable monovalent group; Rf is chosen from a C2-C12 perfluoroalkyl provided that: i) one fluorine atom of the perfluoroalkyl can be optionally replaced by hydrogen, and/or ii) the perfluoroalkyl can be optionally interrupted by at least one oxygen, methylene, or ethylene; Q1 is chosen from the group consisting of a C2-C12 hydrocarbylene optionally interrupted by at least one divalent organic group; X1 is chosen from O or S; —Z2 is —NH— and Z1 is from the group consisting of —O—, and —S—; each R1 is independently chosen from hydrogen, phenyl, or a monovalent C1-C8 alkyl optionally terminated by —C6H5, preferably H or CH3.Type: ApplicationFiled: September 23, 2011Publication date: January 26, 2012Applicant: E.I. DU PONT DE NEMOURS AND COMPANYInventors: Axel Hans-Joachim Herzog, Gerald Oronde Brown
-
Publication number: 20120022267Abstract: The present invention is directed to a fluorosilane represented by (L)3-Si—(CH2)n—N(-Q3-Rf)-Q1-Rf where each n is independently an integer from 1 to 12; L is independently chosen from a hydrolysable or non-hydrolysable monovalent group Rf is chosen from a C2-C12 perfluoroalkyl provided that: i) one fluorine atom of the perfluoroalkyl can be optionally replaced by hydrogen, and/or ii) the perfluoroalkyl can be optionally interrupted by at least one oxygen, methylene, or ethylene; Q1 is chosen from the group consisting of a C2-C12 hydrocarbylene optionally interrupted by at least one divalent organic group; X1 is chosen from O or S; and b) Q1 and Q3 are independently chosen from the group consisting of a C2-C12 hydrocarbylene interrupted by at least one of —C(O)—O— or —O—C(O)—, and optionally further interrupted by at least one divalent organic group.Type: ApplicationFiled: September 23, 2011Publication date: January 26, 2012Applicant: E.I. DU PONT DE NEMOURS AND COMPANYInventors: Axel Hans-Joachim Herzog, Gerald Oronde Brown
-
Patent number: 8058463Abstract: Fluoroalkyl silanes are a class of compounds useful for various industrial purposes. For example, fluoroalkyl silanes which have hydrolysable groups (called hydrolysable fluoroalkyl silanes), are compounds useful as surface treatment agents which provide durable hydrophobic and oleophobic coatings. In general, hydrolysable fluoroalkyl silanes can be represented with the following formula: (RO—)3Si—RT wherein R is H or an alkyl; and RT is a monovalent organic compound terminated by a perfluoroalkyl group. When used to coat a surface, the (RO—)3 moiety reacts (via hydrolysis) with various chemical groups of the surface (e.g., hydroxyl, amine, or other reactive groups) thereby bonding the fluoroalkyl silane to the surface The RT moiety comprises a divalent organic linking group which links the silicon atom to a terminal group rich in fluorine atoms whose unique electronic properties impart desirable hydrophobic and oleophobic properties in a surface coating.Type: GrantFiled: November 26, 2008Date of Patent: November 15, 2011Assignee: E. I. du Pont de Nemours and CompnayInventors: Axel Hans-Joachim Herzog, Gerald Oronde Brown
-
Patent number: 7964552Abstract: This invention relates to surfactant compositions comprising a fluorosurfactant and a siloxane surfactant wherein the fluorosurfactant exhibits a disproportionate effect upon the resulting surfactant composition's ability to lower equilibrium surface tension. The fluorosurfactants and siloxane surfactants identified by the present invention exhibit a desirable disproportionate effect from the fluorosurfactant acting upon the resulting surfactant composition's ability to lower equilibrium surface tension. Because of this disproportionate effect, surfactant compositions of the present invention with no more than 21 weight percent fluorosurfactant have nearly identical ability to lower equilibrium surface tensions compared with surfactant compositions having higher amounts of fluorosurfactant.Type: GrantFiled: November 13, 2007Date of Patent: June 21, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Axel Hans-Joachim Herzog, Shaun Raymond Rinehimer
-
Patent number: 7638589Abstract: A polymer for imparting repellency and stain resistance to substrates is disclosed of Formula 1: (W)a(R2)bSi(R1)2—O—[Si(R1)2—O]n—[Si(W)c(R1)d(R2)e—O]m—Si(R1)2—(W)f(R2)g??1 wherein: a, b, c, d, e, f and g are each independently 0 or 1, provided that (a+b) is 1, (f+g) is 1, and (c+d+e) is 2, each R1 is a C1 to C8 alkyl, each R2 is independently H or C1 to C8 alkyl, optionally containing oxygen, nitrogen, or sulfur, or a combination thereof, and n=0 to 500, m=1 to 100, each W is independently (Rf—X—A—X)p—Y—X— wherein: Rf is a straight or branched perfluoroalkyl group having from about 2 to about 20 carbon atoms, or a mixture thereof, which is optionally interrupted by at least one oxygen atom, each X is independently an organic divalent linking group having from about 1 to about 20 carbon atoms, optionally containing oxygen, nitrogen, or sulfur, or a combination thereof, A is a 1,2,3-triazole, p=1 to 2, Y is O, N, or NR wherein R is H or C1 to C20 alkyl, optionally containing oxygen, nitrogen, or sulfur,Type: GrantFiled: December 19, 2005Date of Patent: December 29, 2009Assignee: E. I. Du Pont De Nemours and CompanyInventors: Erick Jose Acosta, Axel Hans-Joachim Herzog, Martial Jean-Jacques Pabon
-
Publication number: 20090176097Abstract: Inorganic particles hydrophobized with fluorosilanes have been used to impart hydrophobic as well as oleophobic properties as exemplified by U.S. Patent Application, US2006/0222815, filed by Oles et al. which teaches making such hydrophobized particles by the covalent bonding (i.e. grafting) of fluorosilanes upon the surface of inorganic particles (e.g. silica). The fluorosilanes employed by Oles et al. consist of a silicon atom having four bonds, three of which are direct bonds to hydrolysable groups which can react with the surface of an inorganic particle thereby covalently bonding the fluorosilane to particle. The remaining bond is a direct bond from the silicon atom to a perfluoroalkyl group. In contrast, the hydrophobized inorganic particles of the present invention comprise residues from fluorosilanes wherein the silicon atom is first bonded to a divalent organic linking group which in turn is bonded to a perfluoroalkyl group.Type: ApplicationFiled: December 4, 2008Publication date: July 9, 2009Inventors: Gerald Oronde Brown, Axel Hans-Joachim Herzog
-
Publication number: 20090148654Abstract: A composition comprising a polymer prepared by: reacting (a) at least one diisocyanate, polyisocyanate, or mixture thereof, having isocyanate groups, and (b) at least one fluorinated compound selected from the formula (I): Rf1-L-X ??(I) wherein Rf1 is a monovalent, partially or fully fluorinated, linear or branched, alkyl radical having 2 to 100 carbon atoms; optionally interrupted by 1 to 50 oxygen atoms; wherein the ratio of carbon atoms to oxygen atoms is at least 2:1 and no oxygen atoms are bonded to each other; L is a bond or a linear or branched divalent linking group having 1 15 to 20 carbon atoms, said linking group optionally interrupted by 1 to 4 hetero-radicals selected from the group consisting or —O—, —NR—, —S—, —SO—, —SO2—, —N(R)C(O)— wherein R is H or C1-C6 alkyl, and said linking group optionally substituted with CH2Cl; X is an isocyanate-reactive group selected from the group consisting of —OH, —N(R)H, and —SH wherein R is H or C1-C6 alkyl; and thereafter reacting with (c) water and (d) anType: ApplicationFiled: November 11, 2008Publication date: June 11, 2009Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Gerald Oronde Brown, Axel Hans-Joachim Herzog, Timothy Edward Hopkins
-
Publication number: 20090143608Abstract: The present invention provides a method of making sulfur containing fluoroalkyl amines which overcomes the problems previously known methods. Unlike previously known methods, the method of the present invention can achieve higher yields of sulfur containing fluoroalkyl amines without resorting to costly solvents. Furthermore, unlike previously known methods, the method of the present invention can produce oxidized forms of sulfur containing fluoroalkyl amines wherein the sulfur atom thereof is oxidized.Type: ApplicationFiled: November 18, 2008Publication date: June 4, 2009Inventors: Axel Hans-Joachim Herzog, Hollis Thomas Warren, Brent Ryan Gonska
-
Publication number: 20090143598Abstract: Fluoroalkyl silanes are a class of compounds useful for various industrial purposes. For example, fluoroalkyl silanes which have hydrolysable groups (called hydrolysable fluoroalkyl silanes), are compounds useful as surface treatment agents which provide durable hydrophobic and oleophobic coatings. In general, hydrolysable fluoroalkyl silanes can be represented with the following formula: (RO—)3Si—RT wherein R is H or an alkyl; and RT is a monovalent organic compound terminated by a perfluoroalkyl group. When used to coat a surface, the (RO—)3 moiety reacts (via hydrolysis) with various chemical groups of the surface (e.g., hydroxyl, amine, or other reactive groups) thereby bonding the fluoroalkyl silane to the surface The RT moiety comprises a divalent organic linking group which links the silicon atom to a terminal group rich in fluorine atoms whose unique electronic properties impart desirable hydrophobic and oleophobic properties in a surface coating.Type: ApplicationFiled: November 26, 2008Publication date: June 4, 2009Inventors: Axel Hans-Joachim Herzog, Gerald Oronde Brown
-
Publication number: 20080145329Abstract: This invention relates to surfactant compositions comprising a fluorosurfactant and a siloxane surfactant wherein the fluorosurfactant exhibits a disproportionate effect upon the resulting surfactant composition's ability to lower equilibrium surface tension. The fluorosurfactants and siloxane surfactants identified by the present invention exhibit a desirable disproportionate effect from the fluorosurfactant acting upon the resulting surfactant composition's ability to lower equilibrium surface tension. Because of this disproportionate effect, surfactant compositions of the present invention with no more than 21 weight percent fluorosurfactant have nearly identical ability to lower equilibrium surface tensions compared with surfactant compositions having higher amounts of fluorosurfactant.Type: ApplicationFiled: November 13, 2007Publication date: June 19, 2008Inventors: Axel Hans-Joachim Herzog, Shaun Raymond Rinehimer
-
Publication number: 20080145552Abstract: Coating compositions comprise a coating base, a polyoxyalkylene siloxane additive and a fluorochemical wherein the polyoxyalkylene siloxane is of Formulae 1A, 1B, 1C, or 2: (R2)3SiO[Si(R2)2O]y[Si(R2)(R1)O]x[Si(R2)2O]zSi(R2)3Formula 1A (R2)3SiO[Si(R2)2O]x[Si(R2)2R1Formula 1B R1(R2)2SiO[Si(R2)2O]x[Si(R2)2O]Si(R2)2R1Formula 1C wherein each R2 is independently H, alkyl, or aryl; each R1 is a polyoxyalkylene group having the formula 3 as follows: —CnR4pH2n?pQCmR5pH2m?pOZR3Formula 3 wherein each R4 and R5 is independently H, alkyl, or aryl; Q is CnHR4, aryl, CH2CH(OR4), CH2(CH2OR4), S, O, SO, SO2, SO2NR4, OC(O), OC(NR4), NHC(X)NH, or OC(X)NH or triazole; Z is [C2H4O]a and [C3H6O]b in block or random order; X is O or S; m and n are each independently an integer of 2 to 8; a is an integer of 0 to about 30; b is an integer of 0 to about 20; provided that a+b is from 1 to about 50; each R3 is independently H, acyl, CH3, or a linear or branched alkyl or aryl group having 1 to about 20 carbon atType: ApplicationFiled: September 5, 2007Publication date: June 19, 2008Inventors: Mia Genevieve Berrettini, Axel Hans-Joachim Herzog, John Gavenonis, Donald Douglas May, Xianjun Meng
-
Publication number: 20080146820Abstract: This invention relates to surfactant compositions comprising a phosphate fluorosurfactant and a siloxane surfactant wherein the surfactant composition's ability to lower equilibrium surface tension exceeds that of either the phosphate fluorosurfactant or the siloxane surfactant. Because of the synergistic interaction of the phosphate fluorosurfactant and the siloxane surfactant, it is possible to use only small amounts of the more expensive fluorosurfactant in the surfactant composition of the present invention while preserving or improving the ability to lower the equilibrium surface tension of a liquid, such as water.Type: ApplicationFiled: November 13, 2007Publication date: June 19, 2008Inventors: Axel Hans-Joachim Herzog, Shaun Raymond Rinehimer
-
Patent number: 7138551Abstract: A process for reducing the level of perfluoroalkanoic acids, perfluoroalkanoic esters, and perfluoroalkyliodides in fluorinated alcohols comprising heating a fluorinated alcohol, or mixtures thereof, containing said acids, esters, or iodides to a temperature of at least 175° C. in the presence of water and a base additive is disclosed.Type: GrantFiled: November 5, 2004Date of Patent: November 21, 2006Assignee: E. I. du Pont de Nemours and CompanyInventors: Alexander Borisovich Shtarov, Stephen James Getty, Axel Hans-Joachim Herzog
-
Patent number: 6323372Abstract: New icosahedral borohydrates Cs2[closo-B12(OH)12]; Cs[closo-1-H-1-CB11(OH)11]; and closo-1,12-H2-1,12-C2B10(OH)10 are disclosed. Also set forth are their preparation by refluxing the icosahedral boranes [closo-B12H12]2−, [closo-1-CB11H12]− and closo-1,12-(CH2OH)2-1,12-C2B10H10 with a hydroxylating agent, preferably 30%w hydrogen peroxide.Type: GrantFiled: April 10, 2000Date of Patent: November 27, 2001Assignee: The Regents of the University of CaliforniaInventors: M. Frederick Hawthorne, Toralf Peymann, Axel Hans-Joachim Herzog