US5482521A
Expired / Lapsed
US
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Friction modifiers and antiwear additives for fuels and lubricants
Assignee: Mobil Oil AS
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Filing: 1994-05-18
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Granted: 1996-01-09
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Expires: 2014-05-18
Abstract
Abstract The invention relates to lubricant and fuel additives having antiwear and friction reducing properties. The invention also relates to compositions of oils with viscosities appropriate for lubricants, greases produced therefrom, and fuels and methods for making these compositions. Described in this invention are products of nitrogen heterocycles, such as benzotriazole and tolyltriazole, with amines, such as alkyl amines, aliphatic diamines, alicyclic amines, heterocyclic amines, propylene amines, and aliphatic etheramines, that are linked using carbonyl compounds (e.g., aldehyde, ketone or glyoxal). Additionally, products generated by the reaction of carboxylic acids or carboxylic acid generating compounds (e.g., salts or esters) with carbonyl (e.g., aldehyde, ketone or glyoxal) coupled nitrogen heterocycles and amines, including those described above, are also included in this invention. These products can be used in fuels and lubricants to produce improved antiwear and friction reducing properties.
Inventors
- 👤 Noyes L. Avery
- 👤 Edward G. Barry
- 👤 James T. Carey
- 👤 Lisa S. Crocker
- 👤 Flora W. Feng
- 👤 John Hiebert
- 👤 Andrew G. Horodysky
- 👤 Lloyd A. Nelson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 17:20
CPC Classifications
C; C10; C10L; C10L10/00; C10L10/08; C07; C07D; C07D249/00; C07D249/16; C07D249/18; C10L1/00; C10L1/10; C10L1/14; C10L1/143; C10L1/22; C10L1/221; C10L1/232; C10L1/234; C10L1/238; C10L10/02; C10L10/04; C10M; C10M129/00; C10M129/02; C10M129/24; C10M129/26; C10M129/68; C10M129/86; C10M129/92; C10M129/95; C10M133/00; C10M133/02; C10M133/04; C10M133/06; C10M133/08; C10M133/38; C10M133/44; C10M133/48; C10M133/50; C10M149/00; C10M149/12; C10M149/14; C10M159/00; C10M159/12; C10L1/18; C10L1/188; C10L1/1881; C10L1/1883; C10L1/189; C10L1/1895; C10L1/233; C10L1/2335; C10L1/2383; C10L1/2387; C10M2207/00; C10M2207/08; C10M2207/10; C10M2207/12; C10M2207/129; C10M2207/28; C10M2207/34; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/042; C10M2215/22; C10M2215/221; C10M2215/223; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/30; C10M2217/00; C10M2217/04; C10M2217/041; C10M2227/00; C10N; C10N2040/00; C10N2040/02; C10N2040/25; C10N2040/251; C10N2040/252; C10N2040/253; C10N2040/255; C10N2040/28
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
31 words
A compound comprising the reaction product of: (a) at least one nitrogen heterocycle; (b) at least one amine; (c) at least one carbonyl compound; and (d) at least one carboxyl compound.
Claim 2
Dependent Claim
31 words
A compound comprising the reaction product of: (a) at least one nitrogen heterocycle; (b) at least one amine; (c) at least one carbonyl compound; and (d) at least one carboxyl compound.
Claim 3
Dependent Claim
44 words
The compound of claim 1 further comprising: (a) a first reaction product of at least one nitrogen heterocycle; (b) at least one amine; and (c) at least one carbonyl compound; which first reaction product is post reacted with (d) at least one carboxyl compound.
Claim 4
Dependent Claim
80 words
The compound of claim 1 further comprising selecting the carbonyl compound from those with the structural formula: ##STR7## in which R 2 and R 3 independently are hydrogen or linear, branched or cyclic hydrocarbyl or hydrocarbylene generally containing 1 to 200 carbon atoms, which are alkyl, aryl, arylalkyl or alkylaryl, and where the hydrocarbyl or hydrocarbylene group can also generally contain 2 to 200 carbon atoms, and at least one heteroatom which can be oxygen, sulfur, nitrogen, and combinations thereof.
Claim 5
Dependent Claim
114 words
The compound of claim 1 comprising selecting (a) the nitrogen heterocycle from the triazoles characterized by the following structural formula: ##STR8## where R 1 is hydrogen or an alkyl group containing 1 to 60 carbon atoms or an alkyl group containing 2 to 60 carbon atoms and at least one heteroatom which is oxygen, sulfur, nitrogen, and combinations thereof; (b) the amine from an alkyl amine, an alicyclic amine, a heterocyclic amine, an aliphatic diamine, an aliphatic triamine, an oxygenated amine, and mixtures thereof; (c) the carbonyl compound from an aldehyde, a ketone, a dicarbonyl, or mixtures thereof; and (d) the carboxyl compound from a carboxylic acid, carboxylic acid generating compound, or mixtures thereof.
Claim 6
Dependent Claim
61 words
The compound of claim 4 further comprising selecting the dicarbonyl from those with the structure: R.sub.2 COR.sub.3 CO where R 2 and R 3 are independently selected from hydrogen, a linear, branched or cyclical C 1 -C 200 hydrocarbyl or hydrocarbylene or mixture thereof, and where R 2 and R 3 can additionally independently contain sulfur, oxygen, nitrogen and combinations thereof.
Claim 7
Dependent Claim
86 words
The compound of claim 4 further comprising selecting the alkyl amine from those with the structure: R.sub.4 NR.sub.5 R.sub.6 where R 4 , R 5 , and R 6 are independently selected from hydrogen, linear, branched or cyclic C 1 -C 200 hydrocarbyl or hydrocarbylene or a mixture thereof, at least one of R 4 , R 5 , or R 6 must be hydrogen, and where R 4 , R 5 , and R 6 can additionally independently contain sulfur, oxygen, nitrogen and combinations thereof.
Claim 8
Dependent Claim
46 words
The compound of claim 4 comprising further selecting the aliphatic diamine from a diamine which has the structural formula: ##STR9## where R 7 is an alkylene group containing 10 to 30 carbon atoms and R 8 is an alkylene group containing 2 to 4 carbon atoms.
Claim 9
Dependent Claim
58 words
The compound of claim 4 comprising further selecting the aliphatic triamine from a triamine which has the structural formula: R.sub.9 NH(CH.sub.2 CH.sub.2 CH.sub.2)NH(CH.sub.2 CH.sub.2 CH.sub.2)NH.sub.2 where R 9 is selected from hydrogen or C 1 -C 20 linear, branched, or cyclic hydrocarbyl or hydrocarbylene group, and where R 9 can additionally contain sulfur, oxygen, nitrogen and combinations thereof.
Claim 10
Dependent Claim
85 words
The compound of claim 4 wherein the amine is an alkyl amine having the structure: R.sub.10 NR.sub.11 (CH.sub.2 CH.sub.2 CH.sub.2 NH).sub.x CH.sub.2 CH.sub.2 CH.sub.2 NR.sub.12 R.sub.13 where x is 0 to 10, and R 10 , R 11 , R 12 , and R 13 are independently selected from hydrogen, C 1 -C 200 linear, branched or cyclic hydrocarbyl or hydrocarbylene, and where R 10 , R 11 , R 12 , and R 13 can additionally independently contain sulfur, oxygen, nitrogen and combinations thereof.
Claim 11
Dependent Claim
26 words
The compound of claim 4 in which the amine is an oxygenated amine selected from the group consisting of hexoxypropyl-1,3-propylenediamine, heptoxypropyl-1,3-propylenediamine, octoxypropyl-1,3-propylenediamine, nonyloxypropyl-1,3-propylenediamine and mixtures thereof.
Claim 12
Dependent Claim
54 words
The compound of claim 4 further comprising selecting the carboxylic acid from those with the structure: ##STR10## where R 22 , is selected from hydrogen, C 1 -C 30 linear, branched or cyclic hydrocarbyl or hydrocarbylene or a mixture thereof, and where R 22 can additionally contain sulfur, oxygen, nitrogen or a combination thereof.
Claim 13
Dependent Claim
23 words
A fuel composition comprising a major amount of fuel and a minor amount of an additive prepared from the compound of claim 1.
Claim 14
Dependent Claim
27 words
A method of making a fuel comprising blending a major amount of fuel and a minor amount of an additive prepared from the compound of claim 1.
Claim 15
Dependent Claim
26 words
A method of making a fuel comprising blending a major amount of fuel and a minor amount of an additive comprising the compound of claim 2.
Claim 16
Dependent Claim
45 words
The compound of claim 1 wherein the nitrogen heterocycle consists essentially of tolyltriazole; the amine is selected from the group consisting of oleyl amine, N-oleyl-1,3-diamino propane, and combinations thereof; the carbonyl compound consists essentially of glyoxal; and the carboxyl compound consists essentially of oleic acid.
Claim 17
Dependent Claim
60 words
The compound of claim 4 in which the amine is selected from the group consisting of pentylamine, hexylamine, octylamine, dioctylamine, dicocoamine, dioleylamine; 2-ethylhexylamine, isopropylamine, isobutylamine, diisobutylamine, bis(2-ethylhexyl)amine, 1,4-diaminocyclohexane, dicyclohexylamine, hexamethyleneimine or piperidine, morpholine, aminopropylmorpholine or aminoethylpiperazine, N-tallow-1,3-propylenediamine, N-oleyl-1,3-propylenediamine, N-linoleyl-1,3-propylenediamine, N-stearyl-1,3-propylenediamine, N-soya-1,3-propylenediamine, N-cocoyl-1,3-diaminopropane, N-oleyl-1,3-diaminopropane, N-isostearyl-1,3-propylenediamine, N-tallow-1,2-ethylenediamine, N-oleyl-1,2-ethylenediamine, N-linoleyl-1,2-ethylenediamine, N-stearyl-1,2-ethylenediamine, N-soya-1,2-ethylenediamine, N-cocoyl-1,2-diaminoethane, N-oleyl-1,2-diaminoethane, N-isostearyl-1,2-ethylenediamine, diethylene triamine or triamine propane, and mixtures thereof.
Claim 18
Dependent Claim
233 words
The compound of claim 4 in which the amine is an oxygenated amine selected from the group consisting of (a) 3-methoxypropylamine, 3-ethoxypropylamine, 3-propyloxypropylamine, 3-butyloxypropylamine, 3-octyloxypropylamine, 3-hexoxypropylamine, 3-heptoxypropylamine, 3-nonyloxypropylamine or 3-decyloxypropylamine; (b) an ether diamine having the structural formula ##STR11## where a is 1 to 20 and where R 14 is an alkyl group containing 4 to 20 carbon atoms, R 15 is an alkyl group containing 2 to 4 carbon atoms and R 16 is an alkyl group containing 2 to 10 carbon atoms; (c) a polyether primary amine having the structure R.sub.17 --O(C.sub.2 H.sub.3 (R.sub.18)O).sub.n --(C.sub.3 H.sub.6)--NH.sub.2 where R 17 is an alkyl-substituted phenyl group containing 14 to 26 carbon atoms, C 6 to C 30 alkyl group or C 7 to C 30 aralkyl group, n is an integer ranging from 2 to 10, and R 18 is independently an hydrogen atom or a methyl group; and (d) an hydroxyl-containing group having the structure ##STR12## where x and y are integers from 1 to 10 and the sum of x+y is at least 1 and R 19 is selected from hydrogen or C 1 -C 200 linear, branched, or cyclic hydrocarbyl or hydrocarbylene group, and where R 20 and R 21 are independently selected from C 2 -C 10 hydrocarbylene oxide, and where R 19 can additionally contain at least one heteroatom which can be oxygen, sulfur, nitrogen and combinations thereof.
Claim 19
Dependent Claim
50 words
An additive for oils with viscosities appropriate for use as lubricants, greases produced therefrom, and fuels comprising the reaction product of: (a) at least one nitrogen heterocycle comprising tolyltriazole; (b) at least one amine selected from the group consisting of oleyl amine, N-oleyl-1,3,-diamino propane, and combinations thereof; and (c) glyoxal.
Claim 20
Dependent Claim
50 words
An additive for oils with viscosities appropriate for use as lubricants, greases produced therefrom, and fuels comprising the reaction product of: (a) at least one nitrogen heterocycle comprising tolyltriazole; (b) at least one amine selected from the group consisting of oleyl amine, N-oleyl-1,3,-diamino propane, and combinations thereof; and (c) glyoxal.
Claim 21
Dependent Claim
19 words
A fuel composition comprising a major amount of fuel and a minor amount of the additive of claim 18.
Claim 22
Dependent Claim
23 words
A method of making a fuel comprising blending a major amount of fuel and a minor amount of the additive of claim 18.
Claim 23
Dependent Claim
45 words
A fuel composition comprising a major amount of fuel and a minor amount of an additive comprising the reaction product of: (a) at least one nitrogen heterocycle; (b) at least one amine; (c) glyoxal; and (d) at least one carboxyl compound or carboxyl generating compound.
Claim 24
Dependent Claim
45 words
A fuel composition comprising a major amount of fuel and a minor amount of an additive comprising the reaction product of: (a) at least one nitrogen heterocycle; (b) at least one amine; (c) glyoxal; and (d) at least one carboxyl compound or carboxyl generating compound.
References Cited (Backward Citations)
US4153564A
Cited
US4282008A
Cited
US4294585A
Cited
US4376635A
Cited
US4701273A
Cited
US4865622A
Cited
US5232615A
Cited
US5076946A
Cited
US5143634A
Cited
US5407592A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1999-01-08 | 1999-07-10 | 2000-01-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-01-08 | 2003-07-10 | 2004-01-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-01-08 | 2007-07-10 | 2008-01-09 | $7700.00 | Window Closed / Lapsed |