Dow Global Technolgoies LLC

The Dow Chemical Company

Ddp Specialty Electronic Materials US, LLC

Mou Paul

Abhishek Roy

Ian A Tomlinson

Steven Rosenberg

Steven Douglas Jons

XiaoHua Qiu

Tina L Arrowood

Robert C Cieslinski

David D Hawn

Chengli Zu

Aman A Desai

Mark Alan Rickard

Bruce B Gerhart

William E Mickols

Chunming Zhang

Martin H Peery

Joseph D Koob

Matthew J Jansma

Duane R Romer

Patrick S Hanley

Huang Wu

Derek M Stevens

Yasushi Maeda

Anand S Badami

XiaoHua Sam Qiu

Leaelaf Mengistu Hailemariam

Xiao-Hua Qiu

Mark A Rickard

A method for making a composite polyamide membrane comprising a porous support and a thin film polyamide layer, wherein the method includes: i) applying a polar solution comprising a polyfunctional amine monomer, and a non-polar solution comprising a polyfunctional acyl halide monomer to a surface of a porous support and interfacially polymerizing the monomers to form a thin film polyamide layer, wherein the non-polar solution further comprises at least 50 vol % of a Cto Caliphatic hydrocarbon and from 2 to 25 vol % of benzene or benzene substituted with one or more Cto Calkyl groups; and ii) applying an aqueous solution of nitrous acid to the thin film polyamide layer.

Composite polyamide membrane made via interfacial polymerization using a blend of non-polar solvents

A thin film composite polyamide membrane comprising a porous support and a thin film polyamide layer characterized by possessing: i) an azo (&#x2014;N&#x2550;N&#x2014;) content of from 0.40% to 1.00%, as measured by pyrolysis gas chromatography; and ii) a dissociated carboxylate content of at least 0.40 mol/kg as measured by RBS at pH 9.5.

Composite polyamide membrane having azo content and high acid content

A method for making a composite polyamide membrane comprising a porous support and a polyamide layer, including the steps of: i) applying a polar solution comprising a polyfunctional amine monomer and a non-polar solution comprising a polyfunctional acyl halide monomer to a surface of a porous support and interfacially polymerizing the monomers to form a polyamide layer; and ii) exposing the thin film polyamide layer to nitrous acid; wherein the method is characterized by at least one of: conducting the interfacial polymerization of step i) in the presence of a subject amine compound, or applying a subject amine compound to the interfacially polymerized polyamide layer prior to step ii), wherein the subject amine compound is different from the polyfunctional acyl halide and polyfunctional amine monomers. 

Composite polyamide membrane post-treated with nitrous acid

A method for making a composite polyamide membrane including a porous support and a thin film polyamide layer including the steps of applying a polyfunctional amine monomer and a combination amine-reactive compounds to a surface of the porous support and reacting the constituents to form a thin film polyamide layer, wherein the amine-reactive compounds include: i) a polyfunctional amine-reactive monomer including two to three amine-reactive moieties selected from acyl halide, sulfonyl halide and anhydride, ii) a polyfunctional amine-reactive monomer including at least four amine-reactive moieties selected from acyl halide, sulfonyl halide and anhydride, and iii) an acid compound including at least on carboxylic acid moiety or salt thereof and at least one amine-reactive moiety selected from acyl halide and sulfonyl halide.

Membrane derived from polyfunctional amine and combination of different polyfunctional amine-reactive monomers

A method for making a composite polyamide membrane comprising a porous support and a thin film polyamide layer, wherein the method includes the steps of applying a polar solution comprising a polyfunctional amine monomer and a non-polar solution comprising a polyfunctional acyl halide monomer to a surface of a porous support and interfacially polymerizing the monomers to form a thin film polyamide layer. The method is characterized by including a substituted benzamide monomer within the non-polar solution.

Composite polyamide membrane made using substituted benzamide monomer

A method for making a composite polyamide membrane including a porous support and a thin film polyamide layer, wherein the method includes: (i) applying a polar solution comprising a polyfunctional amine monomer and a non-polar solution comprising a polyfunctional acyl halide monomer to a surface of a porous support and interfacially polymerizing the monomers to form a thin film polyamide layer; (ii) treating the thin film polyamide layer with a polyfunctional arene compound; and (iii) exposing the thin film polyamide layer to nitrous acid; wherein the polar and non-polar solutions further comprises at least one of the following: (A) at least one of the solutions further comprises a tri-hydrocarbyl phosphate compound represented by Formula (I): and (B) the non-polar solution further comprises an acid-containing monomer comprising a C-Chydrocarbon moiety substituted with at least one carboxylic acid functional group or salt thereof and at least one amine-reactive functional group. 

Composite polyamide membrane post treated with nitrious acid

A method for making a composite polyamide membrane comprising a porous support and a polyamide layer, including the steps of: i) applying a polar solution comprising of polyfunctional amine monomer and a non-polar solution comprising a polyfunctional acyl halide monomer to a surface of a porous support and interfacially polymerizing the monomers to form a polyamide layer; and ii) exposing the thin film polyamide layer to nitrous acid; wherein the method is characterized by at least one of: conducting the interfacial polymerization of step i) in the presence of a subject amine-reactive compound, or applying a subject amine-reactive compound to the interfacially polymerized polyamide layer prior to step ii), wherein the subject amine-reactive compound is different from the polyfunctional acyl halide and polyfunctional amine monomers and is represented by the following formula: 

A method for making a composite polyamide membrane comprising a porous support and a thin film polyamide layer, wherein the method includes the step of applying a polyfunctional amine monomer and polyfunctional acyl halide monomer to a surface of the porous support and interfacially polymerizing the monomers to form a thin film polyamide layer, wherein the step of applying the polyfunctional acyl halide monomer to the porous support includes the step of combining the polyfunctional acyl halide monomer with a non-polar solvent at a concentration of at least 0.18 weight percent to form a coating solution which is applied to the surface of the porous support, and wherein the interfacial polymerization is conducted in the presence of a tri-hydrocarbyl phosphate compound which is provided in a molar ratio of at least 0.5:1 with the polyfunctional acyl halide monomer. Many additional embodiments are described including membranes made from the subject method and applications for such membranes.

Composite polyamide membrane

A method for making a composite polyamide membrane including a porous support and a thin film polyamide layer, wherein the method includes the step of applying a polyfunctional amine monomer and a tetraacyl acyl halide monomer represented by Formula (I) to a surface of the porous support and interfacially polymerizing the monomers to form a thin film polyamide layer; wherein A is selected from: oxygen (&#x2014;O&#x2014;); carbon (&#x2014;C&#x2014;); silicon (&#x2014;Si&#x2014;); each of which may be unsubstituted or substituted, e.g. with alkyl groups of 1-4 carbon atoms; or a carbonyl group (&#x2014;C(O)&#x2014;), X is the same or different and is selected from a halogen, and Y is selected from halogen and hydroxide. 

Thin film composite membrane derived from tetra-functional acyl halide monomer

A thin film composite polyamide membrane having a porous support and a thin film polyamide layer comprising a reaction product of m-phenylene diamine (mPD) and trimesoyl chloride (TMC), characterized by the thin film polyamide layer having a critical strain value of less than 10%. In another embodiment, the thin film polyamide layer has a modulus of greater than 0.75 (GPa). In yet another embodiment, the thin film polyamide layer has an equilibrium swelling value of at least 45%. In another embodiment, the thin film polyamide layer has a thickness of at least 230 nm.

Composite polyamide membrane with improved structure

A thin film composite polyamide membrane comprising a porous support and a thin film polyamide layer characterized by possessing: i) an azo (&#x2014;N&#x2550;N&#x2014;) content of from 0.30% to 0.80%, as measured by pyrolysis gas chromatography; and ii) a dissociated carboxylate content of at least 0.18 mol/kg as measured by RBS at pH 9.5.

Composite polyamide membrane having high acid content and low azo content

A thin film composite membrane including a porous support and a thin film polyamide layer characterized by having a dissociated carboxylate content of at least 0.45 moles/kg at pH 9.5 and a method for making a composite polyamide applying a polar solution comprising a polyfunctional amine monomer and a non-polar solution comprising a polyfunctional amine-reactive monomer to a surface of the porous support and interfacially polymerizing the monomers to form a thin film polyamide layer, wherein the method is characterized by the non-polar solution comprising at least 0.025 wt % of an acid compound including at least one carboxylic acid moiety and at least one amine-reactive moiety selected from acyl halide and anhydride.

Composite polyamide membrane with increased carboxylic acid functionality

A thin film composite polyamide membrane comprising a porous support and a thin film polyamide layer characterized by possessing an azo (&#x2014;N&#x2550;N&#x2014;) content of from 0.75% to 0.95%, as measured by pyrolysis gas chromatography.

Composite polyamide membrane having preferred azo content

A method for making a composite polyamide membrane comprising a porous support and a polyamide layer, including the steps of: i) applying a polar solution including a polyfunctional amine monomer and a non-polar solution including a polyfunctional acyl halide monomer to a surface of a porous support and interfacially polymerizing the monomers to form a polyamide layer; ii) applying a dihydroxyaryl compound to the polyamide layer, wherein the dihydroxyaryl compound is represented by: formula wherein D, D', D&#x2033; and D&#x2032;&#x2033; are independently selected from: alkyl, alkoxy, hydrogen, halogen, hydroxyl and amine, and L is a linking group; and iii) exposing the thin film polyamide layer to nitrous acid. 

Composite polyamide membrane treated with dihyroxyaryl compounds and nitrous acid

A method for making a composite polyamide membrane comprising the steps of applying a polyfunctional amine monomer and polyfunctional acyl halide monomer to a surface of the porous support and interfacially polymerizing the monomers to form a thin film polyamide layer, wherein the method is includes at least one of the following steps: i) conducting the interfacial polymerization in the presence of a monomer comprising at least one phosphorous-containing functional group or salt thereof and an at least one amine-reactive functional group; and/or ii) applying such a monomer to the thin film polyamide layer.

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Edina, MN, United States of America

Mou Paul