IP Library Patent Application 12608412
Patent Application
App. No. 12/608,412

Lubrication and lubricating oil compositions

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Patent No.
US None
App. No.
12/608,412
Abstract

Monoaryltrialkyl phenylenediamine compounds useful as ashless TBN sources for lubricating oil compositions that are compatible with fluoroelastomeric engine seal materials and meet copper corrosion requirements, and lubricating oil compositions containing such phenylenediamine compounds.

Claims (20)

1 . A crankcase lubricating oil composition such as a heavy duty diesel lubricating oil comprising or made by admixing an oil of lubricating viscosity, in a major amount, and, one or more N-aryl-N′,N′,N′-trialiphatic hydrocarbyl phenylenediamine compounds, in a minor amount, each aliphatic hydrocarbyl group, preferably alkyl, being straight-chained and having 1 to 12, preferably 5 to 12, more preferably 5 to 8 carbon atoms.

2 . A composition as claimed in claim 1 having a TBN measured according to ASTM D4739 of at least 6, such as 6 to 20.

3 . A composition as claimed in claim 1 having a SASH content of no greater than 0.8, mass %.

4 . A composition as claimed in claim 1 wherein at least 10, such as at least 15, or at least 20, such as at least 25% of the compositional TBN as measured by ASTM D4739 is derived from said phenylenediamine compounds, and less than 25, preferably less than 20, % of the compositional TBN is derived from ashless TBN sources other than said phenylenediamine compounds, including basic dispersants.

5 . A composition as claimed in claim 1 which has copper corrosion performance in the high-temperature bench corrosion test (ASTM D6594) that falls within the limits of the API CJ-4 and ACEA E6 specification, and has fluoroelastomeric engine seal materials compatibility performance in the MB-AK6 test that falls within the limits of the MB p228.51 specification.

6 . A concentrate for the preparation of a lubricating oil composition as claimed in claim 1 comprising from 1 to 30 mass % of one or more of said phenylenediamine compounds; 10 to 40 mass % of a nitrogen-containing dispersant; 2 to 20 mass % of an aminic antioxidant, a phenolic antioxidant, a molybdenum compound, or a mixture thereof; 5 to 40 mass % of a detergent; and 2 to 20 mass % of a metal dihydrocarbyl dithiophosphate.

7 . A method of lubricating surfaces of a compression-ignited internal combustion engine during its operation comprising

(a) providing, in a minor amount, one or more N-aryl-N,N′,N′-trialiphatic hydrocarbyl phenylenediamine as defined in claim 1 in a major amount of an oil of lubricating viscosity to make a lubricating oil composition, the TBN of which, as measured by ASTM D4739 is thereby enhanced without concurrently increasing the SASH, and that has copper corrosion performance in the high-temperature bench corrosion test (ASTM D6594) that falls within the limits of the API CJ-4 and ACEA E6 specification, and has fluoroelastomeric engine seal materials compatibility performance in the MB-AK6 test that falls within the limits of the MB p228.51 specification;

(b) providing the lubricating oil composition to the engine crankcase; and

(e) operating said engine.

8 . N-aryl-N,N′,N′-aliphatic hydrocarbyl phenylenediamine of the formula

wherein R 1 is aryl;

each of R 2 , R 3 and R 4 is independently straight chain C 5 to C 12 aliphatic hydrocarbyl, preferably alkyl, most preferably C 5 to C 8 , alkyl;

R 5 , or each R 5 , is independently hydrogen or hydrocarbyl, preferably alkyl, having 1 to 12 carbon atoms; and

n is 0-4.

9 . Phenylenediamine, as claimed in claim 8 , having an average molecular weight of from 450 to 700, such as from 450 to 650, preferably from 500 to 600.

10 . Phenylenediamine, as claimed in claim 8 , wherein the nitrogen atoms are arranged para to one another.

11 . A mixture of phenylenediamine compounds as claimed in any of claims 8 to 10 .

12 . N-Phenyl-N,N′,N′-tri-n-pentyl-p-phenylenediamine.

13 . Phenylenediamine, as claimed in any of claims 8 , 9 , 10 , and 12 , having a TBN, measured as in ASTM D4739, of at least 50, preferably at least 120 mg KOH/g.

Assignments (8)
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 11, 2012
From: CHENG, JIE; EMERT, JACOB; HARTLEY, JOSEPH P.; ROWLAND, ROBERT G.; STIEBER, JOSEPH F.
To: CHEMTURA CORPORATION; INFINEUM INTERNATIONAL LIMITED
Reel/Frame 028026/0544 →
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 16, 2010
From: CHENG, JIE; EMERT, JACOB; HARTLEY, JOSEPH P.; ROWLAND, ROBERT G.; STIEBER, JOSEPH
To: CHEMTURA CORPORATION
Reel/Frame 024084/0285 →
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 →