US3849322A
Expired / Lapsed
US
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Alkylated tertiary amines as high-temperature antioxidants for ester base lubricants
Assignee: WR Grace and Co Conn
•
Filing: 1973-07-16
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Granted: 1974-11-19
•
Expires: 1993-07-16
Abstract
Abstract This invention is directed to an improved ester base lubricant composition which exhibits enhanced oxidative stability in use. This improved lubricant composition comprises a major amount of an ester of a carboxylic acid and a minor amount of; (a) a mixture of a secondary aromatic amine and a tertiary aromatic amine; or (b) a mixture of two tertiary aromatic amines. Other additives can be included in the improved lubricant composition.
Inventors
- 👤 K Wendler
- 👤 D Daniels
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 10:58
CPC Classifications
C; C10; C10M; C10M3/00; C10M2207/00; C10M2207/28; C10M2207/281; C10M2207/282; C10M2207/283; C10M2207/286; C10M2207/30; C10M2207/304; C10M2209/00; C10M2209/10; C10M2209/103; C10M2209/109; C10M2209/11; C10M2209/112; C10M2215/00; C10M2215/02; C10M2215/06; C10M2215/064; C10M2215/065; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/30; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/041; C10M2223/042
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
24 words
LUBRICANT COMPOSITION COMPRISING MAJOR AMOUNTS OF A CARBOXYLIC ACID ESTER LUBRICANT, THE IMPROVEMENT COMPRISING THE PRESENCE OF, A. A SECONDARY AMINE HAVING THE FORMULA,
Claim 2
Dependent Claim
24 words
LUBRICANT COMPOSITION COMPRISING MAJOR AMOUNTS OF A CARBOXYLIC ACID ESTER LUBRICANT, THE IMPROVEMENT COMPRISING THE PRESENCE OF, A. A SECONDARY AMINE HAVING THE FORMULA,
Claim 3
Dependent Claim
10 words
The composition of claim 1 in which R1 is C(CH3)2CH2C(CH3)3.
Claim 4
Dependent Claim
10 words
The composition of claim 1 in which R2 is C(CH3)2CH2C(CH3)3.
Claim 5
Dependent Claim
10 words
The composition of claim 1 in which R3 is C(CH3)2CH2C(CH3)3.
Claim 6
Dependent Claim
10 words
The composition of claim 1 in which R4 is C(CH3)2CH2C(CH3)3.
Claim 7
Dependent Claim
10 words
The composition of claim 1 in which A is CH2CH2.
Claim 8
Dependent Claim
10 words
The composition of claim 1 in which R9 is C(CH3)2CH2C(CH3)3.
Claim 9
Dependent Claim
10 words
The composition of claim 1 in which A is CH2.
Claim 10
Dependent Claim
13 words
The composition of claim 1 in which R6, R7, and R8 are hydrogen.
Claim 11
Dependent Claim
34 words
The composition of claim 1 in which said composition contains 0.5-10 parts of a phosphorus-containing ester selected from the group consisting of tricresyl phosphate, triphenyl phosphate, cresyldiphenyl phosphate, xylyldiphenyl phosphate, triethyl phosphate, tributyl phosphate.
Claim 12
Dependent Claim
16 words
The composition of claim 1 in which said composition contains 0.1 part of an aminosubstituted 1,2,4-triazole.
Claim 13
Dependent Claim
43 words
The composition of claim 1 in which the carboxylic acid ester component of said composition is an ester derived from an aliphatic carboxylic acid having 3-18 carbon atoms and a polyol selected from the group consisting of trimethylolpropane, pentaerythritol, dipentaerythritol, tripentaerythritol, and neopentylglycol.
Claim 14
Dependent Claim
27 words
In a lubricant composition comprising major amounts of a carboxylic acid ester lubricant, the improvement comprising the presence of; a. a first tertiary amine having the formula
Claim 15
Dependent Claim
27 words
In a lubricant composition comprising major amounts of a carboxylic acid ester lubricant, the improvement comprising the presence of; a. a first tertiary amine having the formula
Claim 16
Dependent Claim
10 words
The composition of claim 13 in which R1 is C(CH3)2CH2C(CH3)3.
Claim 17
Dependent Claim
10 words
The composition of claim 13 in which R2 is C(CH3)2CH2C(CH3)3.
Claim 18
Dependent Claim
10 words
The composition of claim 13 in which R3 is C(CH3)2CH2C(CH3)3.
Claim 19
Dependent Claim
10 words
The composition of claim 13 in which R4 is C(CH3)2CH2C(CH3)3.
Claim 20
Dependent Claim
10 words
The composition of claim 13 in which A is CH2CH2.
Claim 21
Dependent Claim
10 words
The composition of claim 13 in which R9 is C(CH3)2CH2C(CH3)3.
Claim 22
Dependent Claim
10 words
The composition of claim 13 in which A is CH2.
Claim 23
Dependent Claim
13 words
The composition of claim 13 in which R6, R7, and R8 are hydrogen.
Claim 24
Dependent Claim
35 words
The composition of claim 13 in which said composition contains 0.5-10 parts of a phosphorus-containing ester selected from the group consisting of tricresyl phosphate, triphenyl phosphate, cresyldiphenyl phosphate, xylyldiphenyl phosphate, Triethyl phosphate and triisooctyl phosphate.
Claim 25
Dependent Claim
16 words
The composition of claim 13 in which said composition contains 0.1 part of an aminosubstituted 1,2,4-triazole.
Claim 26
Dependent Claim
43 words
The composition of claim 13 in which the carboxylic acid ester component of said composition is an ester derived from an aliphatic carboxylic acid having 3-18 carbon atoms and a polyol selected from the group consisting of trimethylolpropane, pentaerythritol, dipentaerythritol, tripentaerythritol and neopentylglycol.
Claim 27
Dependent Claim
36 words
The composition of claim 13 in which the first tertiary amine is selected from the group consisting of N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenylbenzylamine N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-2-phenylethylamine N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-2-methylbenzylamine N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-4-methylbenzylamine N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-2-chlorobenzylamine N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-4-chlorobenzylamine N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-2,4-dichlorobenzylamine, N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-3,4-dichlorobenzylamine, N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl- Alpha , Alpha -dichlorobenzylamine, N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-2-fluorobenzylamine, N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-4-fluorobenzylamine, N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-4-nitrobenzylamine, and N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-2-phenylethylamine.
Claim 28
Dependent Claim
165 words
The composition of claim 13 in which the second tertiary amine is N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Alpha -naphthylbenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Alpha -naphthyl-2-phenylethylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Alpha -naphthyl-2-methylbenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Alpha -napthyl-4-methylbenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Alpha -naphthyl-2-chlorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Alpha -napthyl-4-chlorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Alpha -naphthyl-2,4-dichlorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Alpha -napthyl-3,4-dichlorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Alpha -naphthyl- Alpha - Alpha -dichlorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Alpha -naphthyl-2-fluorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Alpha -napthyl-4-fluorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Alpha -naphthyl-4-nitrobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthylbenzylamines, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthyl-2-phenylethylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthyl-2-methylbenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthyl-4-methylbenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthyl-2-chlorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthyl-4-chlorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthyl-2,4-dichlorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthyl-3,4-dichlorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthyl- Alpha - Alpha -dichlorobenzylamine N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthyl-2-fulorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthyl-4-fluorobenzylamine, N-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthyl-4-nitrobenzylamine, or N-4-(,1,3,3-tetramethylbutyl)-phenyl-N- Beta -1-(1,1,3,3-tetramethylbutyl)- Beta -naphthylbenzylamine. 27. A lubricant composition comprising: a. 100 parts of a carboxylic acid ester b. 0.5-10 parts of tricresyl phosphate; c. 0.5-8 parts of 4,4''-(1,1,3,3-tetramethylbutyl) diphenylamine; d. 0.5-10 parts of a tertiary amine selected from a group consisting of N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-N-Alpha -naphthylbenzylamine, and N,N-bis-4-(1,1,3,3-tetramethylbutyl)-phenyl-N- Beta -naphthylbenzylamine; and e. 0-0.5 parts of a member selected from a third group consisting of 3-amino-1,2,4-triazole, 4-amino-1,2,4-triazole, benzotriazole, 5,5-methylene-bis-(1,2,3-benzotriazole), and a lower alkyl benzotriazole.
Claim 29
Dependent Claim
66 words
A lubricant composition comprising: a. 100 parts of a carboxylic acid ester b. 0.5-10 parts of tricresyl phosphate; c. 0.5-8 parts of a secondary amine selected from the first group consisting of N-4-(1,1,3,3-tetramethylbutyl)phenyl- Alpha -naphthylamine, and N-4-(1,1,3,3-tetramethylbutyl)phenyl- Beta -naphthylamine; d. 0.5-10 parts of N,N-bis-4-(1,1,3,3-tetramethylbutyl) phenylbenzylamine, e. 0-0.5 parts of a member selected from a third group consisting of an amino-1,2,4-triazole, benzotriazole, 5,5-methylene-bis-(1,2,3-benzotriazole), and an alkyl benzotriazole.
Claim 30
Dependent Claim
66 words
A lubricant composition comprising: a. 100 parts of a carboxylic acid ester b. 0.5-10 parts of tricresyl phosphate; c. 0.5-8 parts of a secondary amine selected from the first group consisting of N-4-(1,1,3,3-tetramethylbutyl)phenyl- Alpha -naphthylamine, and N-4-(1,1,3,3-tetramethylbutyl)phenyl- Beta -naphthylamine; d. 0.5-10 parts of N,N-bis-4-(1,1,3,3-tetramethylbutyl) phenylbenzylamine, e. 0-0.5 parts of a member selected from a third group consisting of an amino-1,2,4-triazole, benzotriazole, 5,5-methylene-bis-(1,2,3-benzotriazole), and an alkyl benzotriazole.
Claim 31
Dependent Claim
26 words
In a lubricant composition comprising major amounts of a carboxylic acid ester lubricant, the improvement comprising the presence of; a. a secondary amine having the formula;
Claim 32
Dependent Claim
26 words
In a lubricant composition comprising major amounts of a carboxylic acid ester lubricant, the improvement comprising the presence of; a. a secondary amine having the formula;
Claim 33
Dependent Claim
10 words
The composition of claim 29 in which R1 is C(CH3)2CH2C(CH3)3.
Claim 34
Dependent Claim
10 words
The composition of claim 29 in which A is CH2CH2.
Claim 35
Dependent Claim
10 words
The composition of claim 29 in which R3 is C(CH3)2CH2C(CH3)3.
Claim 36
Dependent Claim
10 words
The composition of claim 29 in which R4 is C(CH3)2CH2C(CH3)3.
Claim 37
Dependent Claim
10 words
The composition of claim 29 in which R5 is C(CH3)2CH2C(CH3)3.
Claim 38
Dependent Claim
10 words
The composition of claim 29 in which R9 is C(CH3)2CH2C(CH3)3.
Claim 39
Dependent Claim
10 words
The composition of claim 29 in which A is CH2.
Claim 40
Dependent Claim
13 words
The composition of claim 29 in which R6, R7, and R8 are hydrogen.
Claim 41
Dependent Claim
37 words
The composition of claim 29 in which said composition contains 0.5-10 parts of a phosphorus-containing ester selected from the group consisting of tricresyl phosphate, triphenyl phosphate, cresyldiphenyl phosphate, xylyldiphenyl phosphate, triethyl phosphate, triButyl phosphate and triisooctyl phosphate.
Claim 42
Dependent Claim
16 words
The composition of claim 29 in which said composition contains 0.1 part of an aminosubstituted 1,2,4-triazole.
Claim 43
Dependent Claim
43 words
The composition of claim 29 in which the carboxylic acid ester component of said composition is an ester derived from an aliphatic carboxylic acid having 3-18 carbon atoms and a polyol selected from the group consisting of trimethylopropane, pentaerythritol, dipentaerythritol, tripentaerythritol, and neopentylglycol.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-11-18 | 1978-05-20 | 1978-11-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-11-18 | 1982-05-20 | 1982-11-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-11-18 | 1986-05-20 | 1986-11-19 | $7700.00 | Window Closed / Lapsed |