IP Library Granted Patent US 7,611,787
Granted Patent B2
US 7,611,787 · App. 11/222,506 · Granted Nov 3, 2009

Colorant treated ion exchange resins, method of making, heat transfer systems and assemblies containing the same, and method of use

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Quick Facts
Patent No.
US 7,611,787
App. No.
11/222,506
Granted
Nov 3, 2009
Kind
B2
Abstract

Disclosed is a colorant treated ion exchange resin comprising at least 15% of exchangeable groups comprising at least one of an ion, a Lewis acid, or a Lewis base resulting from a colorant having a pK a or pK b of greater than 5 in an aqueous solution at 25° C., based on the total number of exchangeable groups. Also disclosed are heat transfer systems, assemblies, fuel cell systems and methods of maintaining a conductivity of less than 200 μS/cm in a heat transfer fluid that employ the disclosed colorant treated ion exchange resins. Finally, a method of making the disclosed colorant treated ion exchange resins is provided.

Claims (31)

1. An ion exchange resin comprising at least 15% by total number of exchangeable groups comprising at least one of an ion, a Lewis acid, or a Lewis base resulting from a colorant having a pK a or pK b of greater than 5 in an aqueous solution at 25° C., based on the total number of exchangeable groups; and

wherein the colorant is of the formula:

R{A k [(B) n R 1 ] m } x

wherein

R is an organic chromophore selected from the group consisting of anthraquinone, triphenylmethane, diphenylmethane, azo containing compounds, disazo containing compounds, trisazo containing compounds, diazo containing compounds, xanthene, acridine, indene, phthalocyanine, azaannulene, nitroso, nitro, diarylmethane, triarylmethane, methine, indamine, azine, oxazine, thiazine, quinoline, indigoid, indophenol, lactone, aminoketone, hydroxyketone, stilbene, thiazole, one or more conjugated aromatic groups, one or more conjugated heterocyclic groups, one or more conjugated C—C double bonds, and combinations thereof;

A is a linking moiety in said chromophore and is selected from the group consisting of O, N and S;

k is 0 or 1;

B is selected from the group consisting of one or more alkyleneoxy or alkoxy groups containing from 1 to 8 carbon atoms;

n is an integer of from 1 to 100;

m is 1 or 2;

x is an integer of from 1 to 5; and

R 1 is selected from the group consisting of H, C 1 -C 6 alkyl or alkoxy groups containing from 1 to 8 carbon atoms, and combinations thereof.

2. The ion exchange resin of claim 1 wherein the colorant is substantially free of functional groups that will form an ionic species due to hydrolysis in an aqueous alcohol solution.

3. The ion exchange resin of claim 2 wherein the colorant is substantially free of functional groups selected from the group consisting of carboxylate groups, sulfonate groups, phosphonate groups, quaternary amines, groups that carry a positive charge, and groups that carry a negative charge.

4. The ion exchange resin of claim 1 wherein the colorant at least one chromophore selected from the group consisting of anthraquinone, triphenylmethane, diphenylmethane, azo containing compounds, disazo containing compounds, trisazo containing compounds, diazo containing compounds, or combinations thereof.

5. An assembly powered by an alternative power source comprising

an alternative power source and

a heat transfer system in thermal communication with the alternative power source, the heat transfer system comprising

a circulation loop defining a flow path for a heat transfer fluid having a conductivity of less than 200 μS/cm, and

an ion exchange resin positioned in the flow path, the ion exchange resin comprising ion exchangeable groups, wherein at least 15% of the total ion exchangeable groups comprise at least one of an ion, a Lewis acid, or a Lewis base resulting from a colorant having a pK a or pK b of greater than 5 in an aqueous solution at 25° C., based on the total number of exchangeable groups; and

wherein the colorant is of the formula:

R{A k [(B) n R 1 ] m } x

wherein

R is an organic chromophore selected from the group consisting of anthraquinone, triphenylmethane, diphenylmethane, azo containing compounds, disazo containing compounds, trisazo containing compounds, diazo containing compounds, xanthene, acridine, indene, phthalocyanine, azaannulene, nitroso, nitro, diarylmethane, triarylmethane, methine, indamine, azine, oxazine, thiazine, quinoline, indigoid, indophenol, lactone, aminoketone, hydroxyketone, stilbene, thiazole, one or more conjugated aromatic groups, one or more conjugated heterocyclic groups, one or more conjugated C—C double bonds, and combinations thereof;

A is a linking moiety in said chromophore and is selected from the group consisting of O, N and S;

k is 0 or 1;

B is selected from the group consisting of one or more alkyleneoxy or alkoxy groups containing from 1 to 8 carbon atoms;

n is an integer of from 1 to 100;

m is 1 or 2;

x is an integer of from 1 to 5; and

R 1 is selected from the group consisting of H, C 1 -C 6 alkyl or alkoxy groups containing from 1 to 8 carbon atoms, and combinations thereof.

Assignments (15)
GRANT OF SECURITY INTEREST IN PATENT RIGHTS Recorded Sep 8, 2024
From: PRESTONE PRODUCTS LLC
To: GOLDMAN SACHS MIDDLE MARKET LENDING CORP. II
Reel/Frame 068892/0272 →
GRANT OF SECURITY INTEREST IN PATENT RIGHTS Recorded Aug 15, 2024
From: PRESTONE PRODUCTS LLC
To: GOLDMAN SACHS MIDDLE MARKET LENDING CORP. II, AS COLLATERAL AGENT
Reel/Frame 068630/0147 →
RELEASE/TERMINATION OF INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jul 8, 2024
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: BIO-LAB, INC.; KIK CUSTOM PRODUCTS INC.; NC BRANDS, L.P.; PRESTONE PRODUCTS CORPORATION
Reel/Frame 068220/0306 →
RELEASE AND TERMINATION OF INTELLECTUAL PROPERTY SECURITY INTEREST Recorded Jul 8, 2024
From: BARCLAYS BANK PLC
To: AQUA CLEAR INDUSTRIES, LLC; ASEPSIS, INC.; BIO-LAB, INC.; HI-LEX LLC; HOMECARE LABS, INC.; KIK CUSTOM PRODUCTS, INC.; KIK INTERNATIONAL, LLC; PRESTONE PRODUCTS CORPORATION; SOLSKYN PERSONAL CARE LLC; SUNBELT POOL PRODUCTS, LLC; JAMES AUSTIN COMPANY; NC BRANDS L.P.; CYGNUS CORPORATION
Reel/Frame 068220/0455 →
ENTITY CONVERSION Recorded Jun 25, 2024
From: PRESTONE PRODUCTS CORPORATION
To: PRESTONE PRODUCTS LLC
Reel/Frame 067826/0319 →
PARTIAL RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Jun 18, 2024
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: PRESTONE PRODUCTS CORPORATION
Reel/Frame 067777/0634 →
PARTIAL RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Jun 18, 2024
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
To: PRESTONE PRODUCTS CORPORATION
Reel/Frame 067777/0649 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Jun 18, 2024
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: PRESTONE PRODUCTS CORPORATION
Reel/Frame 067777/0671 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Jun 18, 2024
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: PRESTONE PRODUCTS CORPORATION
Reel/Frame 067777/0751 →
SECURITY AGREEMENT Recorded Dec 27, 2021
From: AQUA CLEAR INDUSTRIES, LLC; ASEPIS, INC.; BIO-LAB, INC.; HI-LEX LLC; HOMECARE LABS, INC.; KIK CUSTOM PRODUCTS INC.; KIK INTERNATIONAL LLC; PRESTONE PRODUCTS CORPORATION; SOLSKYN PERSONAL CARE LLC; SUNBELT POOL PRODUCTS, LLC; JAMES AUSTIN COMPANY; CYGNUS CORPORATION; NC BRANDS L.P.
To: BARCLAYS BANK PLC
Reel/Frame 058592/0835 →
RELEASE OF INTELLECTUAL PROPERTY SECURITY INTEREST Recorded Jul 29, 2021
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: BIO-LAB, INC.; HI-LEX LLC; HOMECARE LABS, INC.; JAMES AUSTIN COMPANY; KIK INTERNATIONAL LLC; NC BRANDS L.P.; PRESTONE PRODUCTS CORPORATION; SOLSKYN PERSONAL CARE LLC; SUNBELT POOL PRODUCTS, LLC
Reel/Frame 057650/0125 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (NOTES) Recorded Dec 22, 2020
From: BIO-LAB, INC.; KIK CUSTOM PRODUCTS INC.; KIK INTERNATIONAL LLC; PRESTONE PRODUCTS CORPORATION; SOLSKYN PERSONAL CARE LLC; JAMES AUSTIN COMPANY; CYGNUS CORPORATION; NC BRANDS L.P.; AQUA CLEAR INDUSTRIES, LLC; ASEPSIS, INC.; HI-LEX LLC; HOMECARE LABS, INC.; SUNBELT POOL PRODUCTS, LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 055327/0754 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (2019) Recorded Jan 28, 2019
From: APG, INC.; AQUA CLEAR INDUSTRIES, LLC; ASEPSIS, INC.; BIO-LAB, INC.; HI-LEX LLC; HOMECARE LABS, INC.; KIK CUSTOM PRODUCTS INC.; KIK CUSTOM PRODUCTS, INC; KIK INTERNATIONAL LLC; MARIETTA CORPORATION; PRESTONE PRODUCTS CORPORATION; SOLSKYN PERSONAL CARE LLC; SUNBELT POOL PRODUCTS, LLC; JAMES AUSTIN COMPANY; CBI LABORATORIES, INC.; CYGNUS CORPORATION; NC BRANDS L.P.
To: BARCLAYS BANK PLC, AS AGENT
Reel/Frame 048180/0101 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (TERM LOAN) Recorded Jan 23, 2019
From: PRESTONE PRODUCTS CORPORATION
To: BARCLAYS BANK PLC
Reel/Frame 049517/0967 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (ABL) Recorded Jan 23, 2019
From: PRESTONE PRODUCTS CORPORATION
To: BARCLAYS BANK PLC
Reel/Frame 049518/0001 →