IP Library Granted Patent US 8,419,968
Granted Patent B2
US 8,419,968 · App. 12/575,725 · Granted Apr 16, 2013

Lubricants for refrigeration systems

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Quick Facts
Patent No.
US 8,419,968
App. No.
12/575,725
Granted
Apr 16, 2013
Kind
B2
Abstract

A polyol ester suitable for use as a lubricant or a lubricant base stock has a kinematic viscosity at 40° C. less than or equal to 22 cSt and a viscosity index of greater than or equal to 140. The ester comprises a reaction product of (a) at least one polyhydric alcohol having at least 2 primary hydroxyl groups, (b) at least one monocarboxylic acid having 2 to 15 carbon atoms and (c) at least one polycarboxylic acid having 2 to 15 carbon atoms, wherein the number of acid groups derived from the polycarboxylic acid(s) is at least 25% of the total number of acid groups derived from the monocarboxylic and polycarboxylic acids.

Claims (39)

1. A polyol ester suitable for use as a lubricant or a lubricant base stock, the ester having a kinematic viscosity at 40° C. less than or equal to 22 cSt and a viscosity index of greater than or equal to 140 and the ester comprising a reaction product of

(a) at least one polyhydric alcohol having at least 2 primary hydroxyl groups selected from pentaerythritol, dipentaerythritol, tripentaerythritol, tetrapentaerythritol, trimethylolpropane, trimethylolethane, neopentyl glycol and mixtures thereof,

(b) at least one monocarboxylic acid having 2 to 15 carbon atoms wherein from about 25 mole % to about 100 mole % of the at least one monocarboxylic acid, based on total moles of monocarboxylic acid, is one or more linear monocarboxylic acids, and

(c) at least one polycarboxylic acid having 2 to 15 carbon atoms, wherein the number of acid groups derived from the polycarboxylic acid(s) is 25 to 50% of the total number of acid groups derived from the monocarboxylic and polycarboxylic acids.

2. The ester of claim 1 , wherein said at least one polyhydric alcohol is selected from trimethylolpropane, neopentyl glycol and mixtures thereof.

3. The ester of claim 1 , wherein said at least one polyhydric alcohol is neopentylglycol.

4. The ester of claim 1 , wherein said at least one monocarboxylic acid has 5 to 11 carbon atoms.

5. The ester of claim 1 , wherein said at least one monocarboxylic acid has 6 to 10 carbon atoms.

6. The ester of claim 1 , wherein said at least one monocarboxylic acid is selected from butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, 3- methylbutanoic acid, 2-methylbutanoic acid, 2-ethylhexanoic acid, 2,4-dimethylpentanoic acid, 3,3,5-trimethylhexanoic acid, benzoic acid and mixtures thereof.

7. The ester of claim 6 , wherein said at least one monocarboxylic acid comprises a mixture of at least one linear monocarboxylic acid selected from pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, and decanoic acid

and at least one branched monocarboxylic acid selected from 3-methylbutanoic acid, 2-methylbutanoic acid, 2-ethylhexanoic acid, 2,4-dimethylpentanoic acid, and 3,3,5-trimethylhexanoic acid.

8. The ester of claim 7 , wherein said at least one linear monocarboxylic acid comprises n-heptanoic acid.

9. The ester of claim 7 , wherein said mixture comprises about 25 mole % to about 75 mole % of said at least one linear monocarboxylic acid.

10. The ester of claim 6 , wherein (b) comprises n-heptanoic acid.

11. The ester of claim 6 , wherein said at least one polycarboxylic acid comprises adipic acid.

12. The ester of claim 1 , wherein said at least one polycarboxylic acid has 4 to 10 carbon atoms.

13. The ester of claim 1 , wherein said at least one polycarboxylic acid comprises adipic acid.

14. The ester of claim 1 and having a kinematic viscosity at 40° C. less than or equal to 20 cSt.

15. A lubricant blend comprising a mixture of the polyol ester of claim 1 and a further polyol ester having a different kinematic viscosity than said first mentioned polyol ester.

16. The blend of claim 15 wherein said further polyol ester consists essentially of a reaction product of at least one polyhydric alcohol having at least 2 primary hydroxyl groups and at least one monocarboxylic acid.

17. The blend of claim 15 wherein said further polyol ester has a kinematic viscosity at 40° C. greater than or equal to 40 cSt.

18. A working fluid comprising a halogenated hydrocarbon refrigerant and the polyol ester of claim 1 .

19. The working fluid of claim 18 wherein the refrigerant is a hydrofluorocarbon, a fluorocarbon or a mixture thereof.

20. The ester of claim claim 1 comprising a reaction product of (a) neopentylglycol, (b) at least one monocarboxylic acid having 5 to 9 carbon atoms wherein from about 25 mole % to about 100 mole % of the at least one monocarboxylic acid, based on total moles of monocarboxylic acid, is one or more linear monocarboxylic acids, and (c) at least one polycarboxylic acid selected from succinic acid, glutaric acid, adipic acid and mixtures thereof, wherein the number of acid groups derived from the polycarboxylic acid(s) is 25% to 50 of the total number of acid groups derived from the monocarboxylic and polycarboxylic acids.

21. The ester of claim 20 , wherein said at least one polycarboxylic acid comprises adipic acid.

22. A lubricant blend comprising a mixture of the polyol ester of claim 20 and a further polyol ester having a different kinematic viscosity than said first mentioned polyol ester.

23. The blend of claim 22 wherein said further polyol ester consists essentially of a reaction product of at least one polyhydric alcohol having at least 2 primary hydroxyl groups and at least one monocarboxylic acid.

24. The blend of claim 22 wherein said further polyol ester has a kinematic viscosity at 40° C. greater than or equal to 40 cSt.

25. A working fluid comprising a halogenated hydrocarbon refrigerant and the polyol ester of claim 20 .

26. The working fluid of claim 25 wherein the refrigerant is a hydrofluorocarbon, a fluorocarbon or a mixture thereof.

27. The ester of claim 20 , wherein said at least one monocarboxylic acid is selected from pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, 3-methylbutanoic acid, 2-methylbutanoic acid, 2-ethylhexanoic acid, 2,4-dimethylpentanoic acid, 3,3,5-trimethylhexanoic acid, and mixtures thereof.

28. The ester of claim 27 , wherein said at least one monocarboxylic acid comprises n-heptanoic acid and 2-methylbutanoic acid and/or 3,3,5-trimethylhexanoic wherein of about 25 mole% to about 75 mole% of said at least one monocarboxylic acid is n-heptanoic acid.

29. The ester of claim 28 , wherein wherein said at least one polycarboxylic acid comprises adipic acid.

30. A working fluid comprising a halogenated hydrocarbon refrigerant and the polyol ester of claim 28 .

31. The working fluid of claim 30 wherein the refrigerant is a hydrofluorocarbon, a fluorocarbon or a mixture thereof.

32. The ester of claim 27 , wherein said at least one monocarboxylic acid consistis of n-heptanoic acid.

33. The ester of claim 32 , wherein wherein said at least one polycarboxylic acid comprises adipic acid.

34. A working fluid comprising a halogenated hydrocarbon refrigerant and the polyol ester of claim 32 .

35. The working fluid of claim 34 wherein the refrigerant is a hydrofluorocarbon, a fluorocarbon or a mixture thereof.

Assignments (13)
MERGER AND CHANGE OF NAME Recorded Sep 7, 2018
From: CHEMTURA CORPORATION; LANXESS SOLUTIONS US INC.
To: LANXESS SOLUTIONS US INC.
Reel/Frame 046811/0599 →
RELEASE OF AMENDED AND RESTATED SECOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 12, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
Reel/Frame 042452/0759 →
RELEASE OF THIRD LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 12, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
Reel/Frame 042452/0894 →
RELEASE OF FIRST LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 11, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
Reel/Frame 042447/0508 →
RELEASE OF SECOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 11, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
Reel/Frame 042449/0001 →
THIRD LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jul 18, 2014
From: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 033360/0325 →
AMENDED AND RESTATED SECOND LIEN INTELLECTUAL PROPERY SECURITY AGREEMENT Recorded Jul 18, 2014
From: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 033360/0225 →
FIRST LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT. Recorded Mar 21, 2011
From: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 026028/0622 →
INTELLECTUAL PROPERTY SECURITY RELEASE AGREEMENT Recorded Mar 21, 2011
From: CITIBANK, N.A.
To: CHEMTURA CORPORATION; A & M CLEANING PRODUCTS, LLC; ASCK, INC; BIOLAB COMPANY STORE, LLC; AQUA CLEAR INDUSTRIES, LLC; ASEPSIS, INC.; BIOLAB TEXTILES ADDITIVES, LLC; BIOLAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON MONOCHEM, INC.; CNK CHEMICAL REALTY CORPORATION; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GT SEED TREATMENT, INC.; ISCI, INC; GREAT LAKES CHEMICAL GLOBAL, INC.; HOMECARE LABS, INC.; KEM MANUFACTURING CORPORATION; LAUREL INDUSTRIES HOLDINGS, INC.; NAUGATUCK TREATMENT COMPANY; UNIROYAL CHEMICAL COMPANY LIMITED (DELAWARE); MONOCHEM, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC; WRL OF INDIANA, INC.; BIOLAB FRANCHISE COMPANY, LLC
Reel/Frame 026039/0142 →
SECDOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 21, 2011
From: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORORATED; CROMPTON HOLDING CORPORATION; CLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; HAOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
To: BANK OF AMERICA, N. A.
Reel/Frame 027881/0347 →
AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Feb 22, 2010
From: CHEMTURA CORPORATION; A & M CLEANING PRODUCTS, LLC; AQUA CLEAR INDUSTRIES, LLC; ASCK, INC.; ASEPSIS, INC.; BIOLAB COMPANY STORE, LLC; BIOLAB FRANCHISE COMPANY, LLC; BIOLAB TEXTILE ADDITIVES, LLC; BIO-LAB, INC.; CNK CHEMICAL REALTY CORPORATION; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; CROMPTON MONOCHEM, INC.; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; ISCI, INC.; KEM MANUFACTURING CORPORATION; LAUREL INDUSTRIES HOLDINGS, INC.; MONOCHEM, INC.; NAUGATUCK TREATMENT COMPANY; RECREATIONAL WATER PRODUCTS, INC.; UNIROYAL CHEMICAL COMPANY LIMITED (DELAWARE); WEBER CITY ROAD LLC; WRL OF INDIANA, INC.
To: CITIBANK, N.A.
Reel/Frame 023998/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2009
From: CARR, DALE; HUTTER, JEFFREY; HESSELL, EDWARD T.; KELLEY, RICHARD
To: CHEMTURA CORPORATION
Reel/Frame 023393/0680 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 8, 2009
From: CARR, DALE; HUTTER, JEFFREY; HESSELL, EDWARD T; KELLEY, RICHARD
To: CHEMTURA CORPORATION
Reel/Frame 023345/0437 →