IP Library Granted Patent US 8,771,542
Granted Patent B2
US 8,771,542 · App. 12/500,220 · Granted Jul 8, 2014

Heat transfer fluid, additive package, system and method

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Quick Facts
Patent No.
US 8,771,542
App. No.
12/500,220
Granted
Jul 8, 2014
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 (65)

1. A heat transfer fluid, comprising:

less than or equal to 90 weight percent water;

1 to 99 weight percent alcohol;

0.01 to 10 weight percent of a hydroxylated carboxylic acid of formula (I):

(OH) x (R 1 )(COOH) y

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;

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 weight percent is based on the total weight of the heat transfer fluid; and

wherein the heat transfer fluid is free of silicates.

2. A heat transfer fluid comprising:

less than or equal to 90 weight percent water;

1 to 99 weight percent alcohol;

0.01 to 10 weight percent of 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 weight percent is based on the total weight of the heat transfer fluid; and

wherein the heat transfer fluid is free of silicates.

3. The heat transfer fluid of claim 2 , 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.

4. The heat transfer fluid of claim 3 , 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.

5. The heat transfer fluid of claim 4 , wherein m and n are independently 0 to 15.

6. The heat transfer fluid of claim 5 , wherein m and n are independently 0 to 10.

7. The heat transfer fluid of claim 6 , with the proviso that m+n is less than or equal to 16.

8. The heat transfer fluid of claim 4 , 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.

9. The heat transfer fluid of claim 8 , wherein m and n are independently 0 to 15.

10. The heat transfer fluid of claim 9 , wherein m and n are independently 0 to 10, with the proviso that m+n is less than or equal to 16.

11. The heat transfer fluid of claim 8 , wherein the anhydride of the hydroxylated carboxylic acid of formula (V) is of formula (XI):

12. The heat transfer fluid 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.

13. The heat transfer fluid of claim 12 , wherein R 8 is of formula (VIII):

wherein s is 0 to 10.

14. The heat transfer fluid of claim 1 , wherein the salt of the hydroxylated carboxylic acid is of formula (IX):

(OH) x−q (OM) 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.

15. The heat transfer fluid of claim 14 , 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.

16. The heat transfer fluid 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.

17. The heat transfer fluid 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.

18. The heat transfer fluid of claim 17 , 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.

19. A method of treating a heat transfer fluid, comprising:

mixing with the heat transfer fluid an additive package 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 such that the amount of hydroxylated carboxylic acid is 0.01 to 10 weight percent;

wherein the heat transfer fluid comprises less than or equal to 90 weight percent water, 1 to 99 weight percent of an alcohol, or a combination thereof, and is free of silicates; 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 weight percent is based on the total weight of the heat transfer fluid after addition of the additive package.

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

21. The heat transfer fluid 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 heat transfer fluid 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 heat transfer fluid 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 heat transfer fluid 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 heat transfer fluid of claim 1 , further comprising an oxy-anion of molybdenum, tungsten, vanadium, phosphorus, antimony, or a combination thereof.

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

Assignments (23)
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
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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
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To: BARCLAYS BANK PLC
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