# US 8,771,542 B2 · Heat transfer fluid, additive package, system and method

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- Number: US 8,771,542 B2
- Document ID: US8771542B2
- Status: Granted
- Kind: B2
- Application number: 12/500,220
- Filed: 2009-07-09
- Published: 2010-01-14
- Granted: 2014-07-08
- Earliest claimed: 2008-07-11
- Assignees: Prestone Products Corporation
- Applicants: Bo Yang; Aleksei V Gershun; Peter M Woyciesjes
- Inventors: Bo Yang; Aleksei V Gershun; Peter M Woyciesjes
- Web page: https://patentgrep.com/patent/US8771542B2

## CPC

- C09K 5/20: Antifreeze additives therefor, e.g. for radiator liquids (for application to surfaces C09K3/18; inhibiting corrosion by liquids C23F11/00)
- C07C 59/245: containing hydroxy or O-metal groups
- C07C 59/48: containing six-membered aromatic rings
- C09K 5/10: Liquid materials
- C23F 11/10: using organic inhibitors
- C23F 11/124: {Carboxylic acids}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C23F: NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE (working metal by laser beams B23K26/00; desurfacing by applying flames B23K7/00; working of metal by electro-erosion B23H; producing decorative effects by removing surface material, e.g. by engraving, by etching, B44C1/22; electrolytic etching or polishing C25F); INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25

## 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

### Claim 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(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;
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.

### Claim 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):
R2[R4(OH)x(COOH)y−z][R3(COOH)z] (II)
wherein
R2 is monovalent,
R3 has a total valence of 1+z,
R2 and R3 are independently a C1-20 aliphatic group, C6-20 aromatic group, or a combination thereof,
R4 has a total valence of 2+x+y−z, and is a C2-15 aliphatic group, C6-15aromatic 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.

### Claim 3 (depends on 2)

The heat transfer fluid of claim 2, wherein the hydroxylated carboxylic acid is of formula (III):
R5[R7(OH)x(COOH)y−z][R6(COOH)z] (III),
wherein
R5 and [R6(COOH)z] have a total valence of 1, and are independently a C1-20 aliphatic group selected from the group consisting of an alkyl group, an alkenyl group, a cycloalkyl group, a cycloalkenyl group, and a combination thereof,
[R7(OH)x(COOH)y−z] has a total valence of 2, and is a C1-15 aliphatic group selected from the group consisting of an alkylene group, an alkenylene group, a cycloalkylene group, a cycloalkenylene group, and a combination thereof.

### Claim 4 (depends on 3)

The heat transfer fluid of claim 3, wherein the hydroxylated carboxylic acid is of formula (IV):
CH3(CH2)m[R7(OH)x(COOH)y−1](CH2)n(COOH) (IV),
wherein m and n are independently 0 to 19.

### Claim 5 (depends on 4)

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

### Claim 6 (depends on 5)

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

### Claim 7 (depends on 6)

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

### Claim 8 (depends on 4)

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.

### Claim 9 (depends on 8)

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

### Claim 10 (depends on 9)

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.

### Claim 11 (depends on 8)

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

### Claim 12 (depends on 1)

The heat transfer fluid of claim 1, wherein the ester of the hydroxylated carboxylic acid is of formula (VII):
(OH)x(R1)(COOH)y−p(COOR8)p (VII),
wherein p is 1 to 9, with the proviso that p is less than or equal to y, and R8 is a C1-50 hydrocarbyl group.

### Claim 13 (depends on 12)

The heat transfer fluid of claim 12, wherein R8 is of formula (VIII):
wherein s is 0 to 10.

### Claim 14 (depends on 1)

The heat transfer fluid of claim 1, wherein the salt of the hydroxylated carboxylic acid is of formula (IX):
(OH)x−q(OM)q(R1)(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.

### Claim 15 (depends on 14)

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.

### Claim 16 (depends on 1)

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.

### Claim 17 (depends on 1)

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.

### Claim 18 (depends on 17)

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.

### Claim 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(R1)(COOH)y (I),
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 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.

### Claim 20 (depends on 1)

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

### Claim 21 (depends on 20)

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.

### Claim 22 (depends on 1)

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.

### Claim 23 (depends on 1)

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.

### Claim 24 (depends on 1)

The heat transfer fluid of claim 1, further comprising a corrosion inhibitor comprising an azole, a siloxane, a colloidal silica, a C6 to C14 aliphatic or aromatic mono- or di-carboxylic acid, a C6 to C14 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.

### Claim 25 (depends on 1)

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

### Claim 26 (depends on 1)

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.