Oxygenated aromatic amines and use as antioxidants
US-2025250224-A1 · Aug 7, 2025 · US
US9273259B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9273259-B2 |
| Application number | US-201414203643-A |
| Country | US |
| Kind code | B2 |
| Filing date | Mar 11, 2014 |
| Priority date | Mar 15, 2013 |
| Publication date | Mar 1, 2016 |
| Grant date | Mar 1, 2016 |
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The present invention is directed toward compositions suitable for use as dielectric fluids, lubricant fluids and biodiesel fluids. Compositions described herein are obtained from a saturated, unsaturated or combinations of both monol, diol, triol or polyol acyl ester based fluid and/or a non-ester based fluid and 2,4,6-tris(di-C 1 -C 6 -alkylaminomethyl) phenol and/or the carboxylic acid salt of 2,4,6-tris(di-C 1 -C 6 -alkylaminomethyl) phenol. These compositions demonstrate improved oxidative stability and/or hydrolytic stability at higher use temperatures.
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What is claimed is: 1. A stabilized lubricant fluid composition comprising: (a) at least one component selected from the group consisting of: (i) an ester based fluid comprising saturated and/or unsaturated esters of mono-, di-, tri- or polyhydroxyl alcohols; and (ii) a non-ester based fluid selected from the group consisting of mineral oil, silicones, poly(alpha olefins) and combinations thereof; (b) at least one component selected from the group consisting of: (i) 2,4,6-tris(di-C 1 -C 6 -alkylaminomethyl) phenol (TAP); and (ii) a salt of a at least one mono C 12 -C 30 carboxylic fatty acid and TAP having a molar ratio of up to 3 moles of mono C 12 -C 30 carboxylic fatty acid per mole of TAP; and (c) at least one additive selected from the group consisting of antioxidant, antiwear, antisieze and pour point depressant; and wherein the stabilized lubricant fluid composition has an oxidative stability index (OSI) of greater than about 20 hours at 130° C. as measured by AOCS 12b-92. 2. The stabilized lubricant fluid composition of claim 1 , wherein the ester based fluid is selected from the group consisting of vegetable oil, algae oil, animal fat, tall oil fatty acid esters and combinations thereof. 3. The stabilized lubricant fluid composition of claim 2 , wherein the vegetable oil is selected from the group consisting of: soybean oil, rapeseed oil, sunflower oil, safflower oil, castor oil, palm oil, palm kernel oil, coconut oil, camelina oil, olive oil, cottonseed oil, grapeseed oil and combinations thereof. 4. The stabilized lubricant fluid composition of claim 2 , wherein the vegetable oil comprises at least about 75 wt % of a high oleic acid triglyceride composition. 5. The stabilized lubricant fluid composition of claim 1 , wherein the ester based fluid comprises free fatty acids up to about 1 wt %. 6. The stabilized lubricant fluid composition of claim 1 , wherein the TAP is 2,4,6-tris(dimethylaminomethyl) phenol (TDAMP). 7. The stabilized lubricant fluid composition of claim 1 , wherein the mono C 12 -C 30 carboxylic fatty acid is selected from the group consisting of oleic acid, stearic acid, palmitic acid, myristic acid, lauric acid and tall oil. 8. The stabilized lubricant fluid composition of claim 1 , wherein the salt is formed from oleic acid and 2,4,6-tris(dimethylaminomethyl) phenol (TDAMP). 9. The stabilized lubricant fluid composition of claim 1 , wherein the stabilized lubricant fluid composition has an oxidative stability index (OSI) of greater than about 100 hours at 130° C. as measured by AOCS 12b-92. 10. A method for stabilizing a lubricant fluid composition comprising the steps: mixing together at or above ambient temperature: (a) at least one component selected from the group consisting of: (i) an ester based fluid which comprises saturated and/or unsaturated esters of mono-, di-, tri- or polyhydroxyl alcohols; and (ii) a non-ester based fluid selected from the group consisting of mineral oil, silicones, poly(alpha olefins) and combinations thereof; and (b) at least one stabilizing additive selected from the group consisting of: (i) a 2,4,6-tris(di-C 1 -C 6 -alkylaminomethyl) phenol (TAP); and (ii) a salt of a at least one mono C 12 -C 30 carboxylic fatty acid and TAP having a molar ratio of up to 3 moles of mono C 12 -C 30 carboxylic fatty acid per mole of TAP. 11. The stabilized lubricant fluid composition of claim 1 , wherein the ester based fluid is a blend of: (a) at least one ester based fluids selected from the group consisting of a vegetable oil, algae oil, animal fat and tall oil fatty acid ester having kinematic viscosity less than about 50 cSt at 40° C. as measured by ASTM D792-13; and (b) at least one ester based fluid selected from the group consisting of castor oil, hydrogenated castor oil and epoxidized triglyceride having kinematic viscosity greater than about 200 cSt at 40° C. as measured by ASTM D792-13; characterized in that the kinematic viscosity of the stabilized lubricant fluid composition is in the range of from about 40 cSt to less than about 200 cSt at 40° C. as measured by ASTM D792-13. 12. An article or a machine having moving parts wherein the moving parts have surfaces in frictional contact with each other and/or with other adjoining surfaces, and wherein a stabilized lubricant fluid composition of claim 1 coats at least one of the surfaces. 13. A process for operating an article of claim 12 comprising the steps: operating the article at a temperature of greater than about 60° C.
used as base material · CPC title
with tertiary alkyl groups · CPC title
Inhibition of oxidation, e.g. anti-oxidants · CPC title
for compression ignition · CPC title
Mixtures of base-materials and additives · CPC title
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