US2977308A - Tetrahydronaphthylamino compounds - Google Patents
Tetrahydronaphthylamino compounds Download PDFInfo
- Publication number
- US2977308A US2977308A US349976A US34997653A US2977308A US 2977308 A US2977308 A US 2977308A US 349976 A US349976 A US 349976A US 34997653 A US34997653 A US 34997653A US 2977308 A US2977308 A US 2977308A
- Authority
- US
- United States
- Prior art keywords
- compounds
- tetrahydronaphthylamino
- cyclohexyl
- naphthylamine
- tetrahydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 Tetrahydronaphthylamino compounds Chemical class 0.000 title claims description 8
- 239000000654 additive Substances 0.000 claims description 6
- 239000000314 lubricant Substances 0.000 claims description 5
- 239000002480 mineral oil Substances 0.000 claims description 3
- 235000010446 mineral oil Nutrition 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical group [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- PQTLSVRQJMZPSJ-UHFFFAOYSA-N bis(4-chlorophenyl)phosphinic acid Chemical compound C=1C=C(Cl)C=CC=1P(=O)(O)C1=CC=C(Cl)C=C1 PQTLSVRQJMZPSJ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
Definitions
- the present invention relates to compounds of the general formula wherein X stands for a member of the group consisting of 2,977,308 Patented Mar. 28, 1961.
- the new additives may be mixed with other additives for lubricants, for instance with additives which improve the extreme pressure properties of lubricants, particularly with phosphorus compounds described in German Patents 851,237 and 879,138.
- the amount of the tetrahydronaphthylamino compounds to be applied as additives to lubricants can easily be determined by preliminary tests; in general, amounts of about 0.1 to 0.5% will suflice.
- Example 5 parts by weight of N-cyclohexyl-tetrahydro-anaphthyl-amine and 5 parts by weight of the butyl ester of bis-(p-chloro-phenyl)-phosphinic acid are added to 1000 parts by Weight of a refined mineral oil.
- a mineral oil lubricant containing N-cyclohexyltetrahydro-alpha-naphthylamine as an additive is added.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
TETRAHYDRONAPHTHYLAMINO COMPOUNDS Wilhelm Miiller and Max Zimmermann, Leverkusen- Wiesdorf, and Rudolf Stroh, Leverkusen-Bayerwerk, Germany, assignors to Farbenfabriken Bayer Aktiengesellschaft, Leverlrusen, Germany No Drawing. Filed Apr. 20, 1953, Ser. No. 349,976
Claims priority, application Germany Apr. 23, 1952 2 Claims. (Cl. 252-50) The present invention relates to compounds of the general formula wherein X stands for a member of the group consisting of 2,977,308 Patented Mar. 28, 1961.
"the
influences; this applies particularly 'to oils containing tetrahydronaphthylamino compounds whose amino group is substituted by the cyclohexyl radical or by a cyclohexyl radical carrying an alkyl or hydroxyalkyl substituent. If desired, the new additives may be mixed with other additives for lubricants, for instance with additives which improve the extreme pressure properties of lubricants, particularly with phosphorus compounds described in German Patents 851,237 and 879,138. The amount of the tetrahydronaphthylamino compounds to be applied as additives to lubricants can easily be determined by preliminary tests; in general, amounts of about 0.1 to 0.5% will suflice.
The following example serves to illustrate the invention, without however limiting the scope thereof.
Example 5 parts by weight of N-cyclohexyl-tetrahydro-anaphthyl-amine and 5 parts by weight of the butyl ester of bis-(p-chloro-phenyl)-phosphinic acid are added to 1000 parts by Weight of a refined mineral oil.
In the aging test wherein the consumption of oxygen at 150 C. in the presence of copper powder is measured by the pressure decrease by means of a mercury manometer, the oil itself and its mixture with the phosphorus compound show a pressure decrease of mm. Hg within a few minutes; if however N-cyclohexyl-tetrahydro-a-naphthylamine is present, the consumption of oxygen is delayed to such an extent in each case that this decrease in pressure occurs only after 360 minutes.
We claim:
1. N-cyclohexyl-tetrahydro-alpha-naphthylamine.
2. A mineral oil lubricant containing N-cyclohexyltetrahydro-alpha-naphthylamine as an additive.
References Cited in the file of this patent UNITED STATES PATENTS 2,095,897 Winans Oct. 12, 1937 2,109,165 Cramer Feb. 22, 1938 2,131,206 William et al Sept. 27, 1938 2,174,019 Sullivan Sept. 26, 1939 2,633,425 Thompson May 31, 1953 FOREIGN PATENTS 276,571 Great Britain Sept. 1, 1927
Claims (2)
1. N-CYCLOHEXYL-TETRAHYDRO-ALPHA-NAPHTHYLAMINE.
2. A MINERAL OIL LUBRICANT CONTAINING N-CYCLOHEXYLTETRAHYDRO-ALPHA-NAPHTHYLAMINE AS AN ADDITIVE.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2977308X | 1952-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2977308A true US2977308A (en) | 1961-03-28 |
Family
ID=8050808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US349976A Expired - Lifetime US2977308A (en) | 1952-04-23 | 1953-04-20 | Tetrahydronaphthylamino compounds |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2977308A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3534055A (en) * | 1966-07-16 | 1970-10-13 | Aspro Nicholas Ltd | Certain substituted 1-amino-1,2,3,4-tetrahydro naphthalenes and pharmaceutically acceptable salts thereof |
| US4335006A (en) * | 1979-05-31 | 1982-06-15 | Uniroyal, Inc. | Method of stabilizing lubricating fluids |
| US4962234A (en) * | 1979-05-31 | 1990-10-09 | Uniroyal Chemical Company, Inc. | Antioxidant for polyester fluids - alpha - methyl - n phenylbenzenemethanamine |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB276571A (en) * | 1927-02-24 | 1927-09-01 | Chem Ind Basel | Manufacture of aromatic tetrahydronaphthylamines or derivatives thereof |
| US2095897A (en) * | 1936-04-23 | 1937-10-12 | Wingfoot Corp | Hydrogenation of aryl naphthylamines |
| US2109165A (en) * | 1932-07-02 | 1938-02-22 | Wingfoot Corp | Process of preserving rubber and product |
| US2131206A (en) * | 1934-03-28 | 1938-09-27 | Du Pont | Preservation of rubber |
| US2174019A (en) * | 1936-11-27 | 1939-09-26 | Standard Oil Co | Lubricant |
| US2633425A (en) * | 1950-09-16 | 1953-03-31 | Universal Oil Prod Co | Stabilization of organic compounds |
-
1953
- 1953-04-20 US US349976A patent/US2977308A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB276571A (en) * | 1927-02-24 | 1927-09-01 | Chem Ind Basel | Manufacture of aromatic tetrahydronaphthylamines or derivatives thereof |
| US2109165A (en) * | 1932-07-02 | 1938-02-22 | Wingfoot Corp | Process of preserving rubber and product |
| US2131206A (en) * | 1934-03-28 | 1938-09-27 | Du Pont | Preservation of rubber |
| US2095897A (en) * | 1936-04-23 | 1937-10-12 | Wingfoot Corp | Hydrogenation of aryl naphthylamines |
| US2174019A (en) * | 1936-11-27 | 1939-09-26 | Standard Oil Co | Lubricant |
| US2633425A (en) * | 1950-09-16 | 1953-03-31 | Universal Oil Prod Co | Stabilization of organic compounds |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3534055A (en) * | 1966-07-16 | 1970-10-13 | Aspro Nicholas Ltd | Certain substituted 1-amino-1,2,3,4-tetrahydro naphthalenes and pharmaceutically acceptable salts thereof |
| US4335006A (en) * | 1979-05-31 | 1982-06-15 | Uniroyal, Inc. | Method of stabilizing lubricating fluids |
| US4962234A (en) * | 1979-05-31 | 1990-10-09 | Uniroyal Chemical Company, Inc. | Antioxidant for polyester fluids - alpha - methyl - n phenylbenzenemethanamine |
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