US2977308A - Tetrahydronaphthylamino compounds - Google Patents

Tetrahydronaphthylamino compounds Download PDF

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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
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United States
Prior art keywords
compounds
tetrahydronaphthylamino
cyclohexyl
naphthylamine
tetrahydro
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Expired - Lifetime
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US349976A
Inventor
Muller Wilhelm
Zimmermann Max
Stroh Rudolf
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Bayer AG
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Bayer AG
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    • 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.

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  • 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.
US349976A 1952-04-23 1953-04-20 Tetrahydronaphthylamino compounds Expired - Lifetime US2977308A (en)

Applications Claiming Priority (1)

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DE2977308X 1952-04-23

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Cited By (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (6)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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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