US4778609A
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Hydrogen sulfide suppression with amine derivative
Assignee: Lubrizol Corp
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Filing: 1987-11-18
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Granted: 1988-10-18
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Expires: 2007-11-18
Abstract
Abstract Functional fluids such as metal working fluids are disclosed which include an oil of lubricating viscosity, a sulfurized organic compound, and an amine derivative. The amine derivative is a hindered imine which is the reaction product obtained from reacting a primary amine connected to a tertiary alkyl group with an aldehyde or aldehyde reaction synthon. The inclusion of the hindered imine within the metal working fluid suppresses the generation of hydrogen sulfide gases during the use of the fluid thus improving the environmental and safety characteristics of the fluid.
Inventors
- 👤 Frederick W. Koch
- 👤 Robert L. Floyd
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 11:51
CPC Classifications
C; C07; C07G; C07G99/00; C07G99/002; C10; C10M; C10M135/00; C10M135/02; C10M135/04; C10M135/06; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2219/00; C10M2219/02; C10M2219/022; C10M2219/024; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/041; C10M2223/045; C10M2229/00; C10M2229/02; C10M2229/04; C10M2229/05; C10N; C10N2010/00; C10N2010/04; C10N2040/00; C10N2040/20; C10N2040/22; C10N2040/24; C10N2040/241; C10N2040/242; C10N2040/243; C10N2040/244; C10N2040/245; C10N2040/246; C10N2040/247; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
63 words
A functional fluid, comprising: (A) an oil of lubricating viscosity; (B) a sulfurized organic compound selected from the group consisting of fats, alpha-olefins, fatty acid esters and triglycerides; and (C) a hindered imine of general structural formula (I): ##STR4## wherein R 1 , R 2 , R 3 and R 4 are each independently an alkyl moiety containing 1 to 14 carbon atoms.
Claim 2
Dependent Claim
63 words
A functional fluid, comprising: (A) an oil of lubricating viscosity; (B) a sulfurized organic compound selected from the group consisting of fats, alpha-olefins, fatty acid esters and triglycerides; and (C) a hindered imine of general structural formula (I): ##STR4## wherein R 1 , R 2 , R 3 and R 4 are each independently an alkyl moiety containing 1 to 14 carbon atoms.
Claim 3
Dependent Claim
14 words
The fluid as claimed in claim 1, wherein R 4 is CH 2 .
Claim 4
Dependent Claim
27 words
The fluid as claimed in claim 2, wherein R 1 , R 2 and R 3 each independently an alkyl moiety containing 1 to 9 carbon atoms.
Claim 5
Dependent Claim
42 words
The fluid as claimed in claim 3, wherein the hindered imine (C) is present in the fluid in an amount in the range of from about 0.01% to about 5% by weight based on the weight of the fluid as a whole.
Claim 6
Dependent Claim
48 words
The fluid as claimed in claim 4, wherein the hindered imine (C) is present in an amount in the range of from about 0.10% to about 2.0% by weight based on the weight of the fluid as a whole and the functional fluid is a metal working fluid.
Claim 7
Dependent Claim
80 words
A metal working fluid, comprising: (A) an oil of lubricating viscosity; (B) a sulfurized organic compound selected from the group consisting of fats, fatty acid esters, alpha-olefins and triglycerides; and (C) a hindered imine produced by reacting a primary amine connected to a tertiary alkyl group of general formula (II): ##STR5## wherein R 1 , R 2 and R 3 are each independently an alkyl moiety containing 1 to about 14 carbon atoms, with an aldehyde or aldehyde reaction synthon.
Claim 8
Dependent Claim
80 words
A metal working fluid, comprising: (A) an oil of lubricating viscosity; (B) a sulfurized organic compound selected from the group consisting of fats, fatty acid esters, alpha-olefins and triglycerides; and (C) a hindered imine produced by reacting a primary amine connected to a tertiary alkyl group of general formula (II): ##STR5## wherein R 1 , R 2 and R 3 are each independently an alkyl moiety containing 1 to about 14 carbon atoms, with an aldehyde or aldehyde reaction synthon.
Claim 9
Dependent Claim
31 words
The metal working fluid as claimed in claim 6, wherein the sulfurized organic compound (B) is obtained by reacting elemental sulfur with the organic compound in the presence of a catalyst.
Claim 10
Dependent Claim
53 words
The metal working fluid as claimed in claim 7, wherein the catalyst is selected from the group consisting of phosphoric acid and salts thereof effective in catalyzing the sulfurization of the organic compound and the reacting is carried out at a temperature in the range of about 100° C. to about 250° C.
Claim 11
Dependent Claim
52 words
The metal working fluid as claimed in claim 8, wherein the sulfurized organic compound of (B) is present in an amount of 0.1% to 20% by weight and the hindered imine (C) is present in an amount of about 0.1% to about 5% by weight based on the weight of the fluid.
Claim 12
Dependent Claim
15 words
The metal working fluid of claim 6, wherein the amine of formula (II) is t-butylamine.
Claim 13
Dependent Claim
17 words
The metal working fluid of claim 6, wherein the amine of formula (II) is reacted with paraformaldehyde.
Claim 14
Dependent Claim
20 words
The metal working fluid of claim 9, wherein the amine of formula (II) is t-butylamine which is reacted with paraformaldehyde.
Claim 15
Dependent Claim
83 words
A metal working fluid, comprising: (A) an oil of lubricating viscosity; (B) a sulfurized organic compound obtained by reacting an unsaturated aliphatic compound containing 12 to 28 carbon atoms with elemental sulfur in the presence of a catalyst selected from the group consisting of phosphoric acid and salts thereof; and (C) a hindered imine of the following general structural formula: ##STR6## wherein R 1 , R 2 , and R 3 are each independently an alkyl moiety containing 1 to 9 carbon atoms.
Claim 16
Dependent Claim
83 words
A metal working fluid, comprising: (A) an oil of lubricating viscosity; (B) a sulfurized organic compound obtained by reacting an unsaturated aliphatic compound containing 12 to 28 carbon atoms with elemental sulfur in the presence of a catalyst selected from the group consisting of phosphoric acid and salts thereof; and (C) a hindered imine of the following general structural formula: ##STR6## wherein R 1 , R 2 , and R 3 are each independently an alkyl moiety containing 1 to 9 carbon atoms.
Claim 17
Dependent Claim
49 words
The fluid as claimed in claim 13, wherein the sulfurized organic compound (B) is present in an amount of 0.1% to 20% by weight and the hindered imine (C) is present in an amount of about 0.1% to about 5% by weight based on the weight of the fluid.
Claim 18
Dependent Claim
30 words
The fluid as claimed in claim 14, wherein the aliphatic compound is selected from the group consisting of a fatty acid and a fatty acid ester of a monohydric alcohol.
Claim 19
Dependent Claim
20 words
The fluid as claimed in claim 15, wherein the aliphatic compound is a fatty acid containing 14 to 22 carbons.
Claim 20
Dependent Claim
13 words
The fluid as claimed in claim 13, wherein the catalyst is phosphoric acid.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-10-18 | 1992-04-18 | 1992-10-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-10-18 | 1996-04-18 | 1996-10-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-10-18 | 2000-04-18 | 2000-10-18 | $7700.00 | Window Closed / Lapsed |