IP Library Granted Patent US 9,267,067
Granted Patent B2
US 9,267,067 · App. 14/325,990 · Granted Feb 23, 2016

Heat transfer fluid, additive package, system and method

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Quick Facts
Patent No.
US 9,267,067
App. No.
14/325,990
Granted
Feb 23, 2016
Kind
B2
Abstract

Disclosed herein is a heat transfer fluid, comprising a hydroxylated carboxylic acid of formula (OH)x(R1)(COOH)y, wherein x is 2 to 10, y is 3 to 10, and R1 is a C2-50 aliphatic group, a C6-50 aromatic group, or a combination thereof; and wherein the hydroxylated carboxylic acid comprises the hydroxylated carboxylic acid, an ester thereof, a salt thereof, an anhydride thereof, or a combination thereof. A heat transfer system comprises an aluminum component, a magnesium component, or an aluminum component and a magnesium component; and the foregoing heat transfer fluid.

Claims (58)

1. A method of transferring heat, comprising:

contacting a heat transfer system comprising an aluminum component, a magnesium component, or an aluminum component and a magnesium component with the heat transfer fluid, the heat transfer fluid comprising:

a hydroxylated carboxylic acid of formula (I):

(OH) x (R 1 )(COOH) y   (I),

wherein x is 2 to 10, y is 3 to 10, and R 1 is a C 2-50 aliphatic group, a C 6-50 aromatic group, or a combination thereof; and

wherein the hydroxylated carboxylic acid comprises the hydroxylated carboxylic acid, an ester thereof, a salt thereof, an anhydride thereof, or a combination thereof; and

wherein the heat transfer fluid is free of silicates.

2. The method of claim 1 , wherein the heat transfer fluid comprises about 0.01 to 10 weight percent of the hydroxylated carboxylic acid.

3. A method of transferring heat comprising:

contacting a heat transfer system comprising an aluminum component, a magnesium component, or an aluminum component and a magnesium component with the heat transfer fluid, the heat transfer fluid comprising:

a hydroxylated carboxylic acid of formula (II):

R 2 [R 4 (OH) x (COOH) y-z ][R 3 (COOH) z ]  (II),

wherein

R 2 is monovalent,

R 3 has a total valence of 1+z,

R 2 and R 3 are independently a C 1-20 aliphatic group, C 6-20 aromatic group, or a combination thereof,

R 4 has a total valence of 2+x+y-z, and is a C 2-15 aliphatic group, C 6-15 aromatic group, or a combination thereof,

z is 1 to 8, with the proviso that y-z is greater than or equal to 2,

wherein the hydroxylated carboxylic acid comprises the hydroxylated carboxylic acid, an ester thereof, a salt thereof, an anhydride thereof, or a combination thereof; and

wherein the heat transfer fluid is free of silicates.

4. The method of claim 3 , wherein the hydroxylated carboxylic acid is of formula (III):

R 5 [R 7 (OH) x (COOH) y-z ][R 6 (COOH) z ]  (III),

wherein

R 5 and [R 6 (COOH) z ] have a total valence of 1, and are independently a C 1-20 aliphatic group selected from the group consisting of an alkyl group, an alkenyl group, a cycloalkyl group, a cycloalkenyl group, and a combination thereof,

[R 7 (OH) x (COOH) y-z ] has a total valence of 2, and is a C 1-15 aliphatic group selected from the group consisting of an alkylene group, an alkenylene group, a cycloalkylene group, a cycloalkenylene group, and a combination thereof.

5. The method of claim 4 , wherein the hydroxylated carboxylic acid is of formula (IV):

CH 3 (CH 2 ) m [R 7 (OH) x (COOH) y-1 ](CH 2 ) n (COOH)  (IV),

wherein m and n are independently 0 to 19.

6. The method of claim 2 , wherein m and n are independently 0 to 15.

7. The method of claim 6 , wherein m and n are independently 0 to 10.

8. The method of claim 7 , with the proviso that m+n is less than or equal to 16.

9. The method of claim 5 , wherein the hydroxylated carboxylic acid is selected from the group consisting of:

a hydroxylated carboxylic acid of formula (V):

a hydroxylated carboxylic acid of formula (VI):

and a combination thereof.

10. The method of claim 9 , wherein m and n are independently 0 to 15.

11. The method of claim 10 , wherein m and n are independently 0 to 10, with the proviso that m+n is less than or equal to 16.

12. The method of claim 9 , wherein the anhydride of the hydroxylated carboxylic acid of formula (V) is of formula (XI):

13. The method of claim 1 , wherein the ester of the hydroxylated carboxylic acid is of formula (VII):

(OH) x (R 1 )(COOH) y-p (COOR 8 ) p   (VII),

wherein p is 1 to 9, with the proviso that p is less than or equal to y, and R 8 is a C 1-50 hydrocarbyl group.

14. The method of claim 13 , wherein R 8 is of formula (VIII):

wherein s is 0 to 10.

15. The method of claim 1 , wherein the salt of the hydroxylated carboxylic acid is of formula (IX):

(OH) x-q (0M) q (R 1 )(COOH) y-p (COOM) p   (IX),

wherein q is 1 to 9, with the proviso that q is less than or equal to x, and M comprises an organic cation, an inorganic cation, or a combination thereof.

16. The method of claim 15 , wherein M comprises an alkali metal cation, an alkaline earth metal cation, a transition metal cation, an ammonium cation, a phosphonium cation, a pyridinium cation, an imidazolinium cation, a pyrazolinium cation, a triazolinium cation, a tetrazolinium cation, or a combination thereof.

17. The method of claim 1 , wherein the anhydride of the hydroxylated carboxylic acid is of formula (X):

wherein v is 2, 4, 6, 8, or 10, with the proviso that v is less than or equal to y.

18. The method of claim 1 , comprising about 0.01 percent by weight to about 10 percent by weight of the hydroxylated carboxylic acid, based on the total weight of the heat transfer fluid.

19. The method of claim 18 , comprising about 0.1 percent by weight to about 5 percent by weight of the hydroxylated carboxylic acid, based on the total weight of the heat transfer fluid.

20. The method of claim 1 , wherein the heat transfer fluid further comprises a monohydric alcohol, a polyhydric alcohol, or a combination thereof.

21. The method of claim 20 , wherein the alcohol is selected from the group consisting of methanol, ethanol, propanol, butanol, furfural, tetrahydrofurfurol, ethoxylated furfural, alkoxy alkanol, ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, dipropylene glycol, butylene glycol, glycerol, glycerol-1,2-dimethyl ether, glycerol-1,3 dimethyl ether, monoethylether of glycerol, sorbitol, 1,2,6-hexanetriol, trimethylol propane, and a combination thereof.

22. The method of claim 1 comprising about 0 to about 99.9 percent by weight of the alcohol, based on the total weight of the heat transfer fluid.

23. The method of claim 1 , comprising about 1 to about 60 percent by weight of the water, based on the total weight of the heat transfer fluid.

24. The method of claim 1 , further comprising a corrosion inhibitor comprising an azole, a siloxane, a colloidal silica, a C 6 to C 14 aliphatic or aromatic mono- or di-carboxylic acid, a C 6 to C 14 aliphatic or aromatic mono- or di-carboxylate, a tall oil fatty acid, a borate, a nitrate, a nitrite, an alkali metal salt thereof, an alkaline earth metal salt thereof, an ammonium salt thereof, an amine salt thereof, or a combination thereof.

25. The method of claim 1 , further comprising an oxy-anion of molybdenum, tungsten, vanadium, phosphorus, antimony, or a combination thereof.

26. The method of claim 1 , further comprising a colorant, an antifoam agent, a wetting agent, a biocide, a bitterant, a dispersant or a combination thereof.

Assignments (15)
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 →
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 (ABL) Recorded Jan 23, 2019
From: PRESTONE PRODUCTS CORPORATION
To: BARCLAYS BANK PLC
Reel/Frame 049518/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (TERM LOAN) Recorded Jan 23, 2019
From: PRESTONE PRODUCTS CORPORATION
To: BARCLAYS BANK PLC
Reel/Frame 049517/0967 →
RELEASE OF SECURITY INTEREST Recorded Sep 14, 2016
From: BARCLAYS BANK PLC
To: APG, INC.; AQUA CLEAR INDUSTRIES, LLC; ASEPSIS, INC.; BIO-LAB, INC.; CYGNUS CORPORATION; HI-LEX LLC; HOMECARE LABS, INC.; KIK CUSTOM PRODUCTS INC.; KIK CUSTOM PRODUCTS, INC; KIK INTERNATIONAL LLC; MARIETTA CORPORATION; SOLSKYN PERSONAL CARE LLC; KIK NEW JERSEY, LLC; PRESTONE PRODUCTS CORPORATION
Reel/Frame 040031/0793 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Apr 5, 2016
From: APG, INC.; AQUA CLEAR INDUSTRIES, LLC; ASEPSIS, INC.; BIO-LAB, INC.; CYGNUS CORPORATION; HI-LEX LLC; HOMECARE LABS, INC.; KIK CUSTOM PRODUCTS, INC. (TEXAS); KIK CUSTOM PRODUCTS INC. (DELAWARE); KIK INTERNATIONAL LLC; MARIETTA CORPORATION; PRESTONE PRODUCTS CORPORATION; SOLSKYN PERSONAL CARE LLC; KIK NEW JERSEY, LLC
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 038354/0938 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 21, 2014
From: YANG, BO; GERSHUN, ALEKSEI V.; WOYCIESJES, PETER M.
To: PRESTONE PRODUCTS CORPORATION
Reel/Frame 033583/0517 →