Norbornyl dithiocarbamates

• US 4,876,375 A
• Filed: 05/02/1988
• Issued: 10/24/1989
• Est. Priority Date: 05/02/1988
• Status: Expired due to Fees

• Current Assignee: Ethyl Petroleum Additives Incorporated (Newmarket Corporation)
• Original Assignee: Ethyl Petroleum Additives Incorporated (Newmarket Corporation)
• Inventors: Lam, William Y.
• Primary Examiner(s): Lee, Mary C.
• Assistant Examiner(s): Whittenbaugh, Robert C.
• Application Number:
  US07/189,101
• Time in Patent Office: 540 Days
• Field of Search: 252/47.5, 558/235
• US Class Current: 558/235
• CPC Class Codes: C07C 2602/42 the bicyclo ring system containing seven carbon atoms
• CPC Class Codes: C07C 329/18 having sulfur atoms of dithiocarbonic groups bound to carbon atoms of rings other than six-membered aromatic rings
• CPC Class Codes: C10M 135/18 thiocarbamic type, e.g. containing the groups
• CPC Class Codes: C10M 135/32 Heterocyclic sulfur, selenium or tellurium compounds
• CPC Class Codes: C10M 2219/066 Thiocarbamic type compounds
• CPC Class Codes: C10M 2219/09 Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
• CPC Class Codes: C10N 2070/02 Concentrating of additives

Abstract

Compounds having the formula: ##STR1## wherein: a. each of R, R² and R⁴ when taken singly is a hydrogen atom, an alkyl group containing from 1 to about 15 carbon atoms, an aryl group containing from 6 to about 15 carbon atoms or a cycloalkyl group containing from 4 to about 10 carbon atoms;

b. each of R¹ and R³ when taken singly is a hydrogen atom, an alkyl group containing from 1 to about 15 carbon atoms; an aryl group containing from 6 to about 15 carbon atoms; a cycloalkyl group containing from 4 to about 10 carbon atoms or an alkenyl group containing from 2 to about 10 carbon atoms or R¹ and R³ taken together form the group --CHYCY═CY-- in which Y is a hydrogen atom or a methyl group of R¹ together with R² form an alkylidene group containing from 1 to about 6 carbon atoms;

c. R⁵ is a hydrogen atom or an alkyl group containing from 1 to about 15 carbon atoms;

d. R⁶ is an organic radical selected from an alkyl group, an alkenyl group, an aryl group or an aralkyl group in which the alkyl or alkenyl groups contain up to 32 carbon atoms and the aryl or aralkyl groups contain up to 15 carbon atoms each; and

e. R⁷ is hydrogen or an organic radical selected from an alkyl group or alkenyl group, an aryl or aralkyl group in which the alkyl or alkenyl groups contain up to 32 carbon atoms and the aryl or aralkyl groups contain up to 15 carbon atoms each,

are effective antiwear and antioxidant additives in lubricating oils.

Claims

1. Compounds having the formula:

##STR7## wherein;

a. each of R, R² and R⁴ when taken singly is a hydrogen atom, an alkyl group containing from 1 to 15 carbon atoms, an aryl group consisting of a benzene or a naphthalene group containing from 6 to 15 carbon atoms or a cycloalkyl group containing from 4 to 10 carbon atoms;

b. each of R¹ and R³ when taken singly is a hydrogen atom, an alkyl group containing from 1 to 15 carbon atoms;

an aryl group consisting of a benzene or a naphthalene group containing from 6 to 15 carbon atoms;

a cycloalkyl group containing from 4 to 10 carbon atoms or an alkenyl group containing from 2 to 10 carbon atoms or R¹ or R³ taken together form the group --CHYCY═

CY-- in which Y is a hydrogen atom or a methyl group or R¹ together with R² form an alkylidene group containing from 1 to 6 carbon atoms;

c. R⁵ is a hydrogen atom or an alkyl group containing from 1 to 15 carbon atoms;

d. R⁶ is an organic radical selected from an alkyl group, an alkenyl group, an aryl group or an aralkyl group in which the alkyl or alkenyl groups contain up to 32 carbon atoms and the aryl or aralkyl groups are selected from benzene and naphthalene groups which contain up to 15 carbon atoms each; and

e. R⁷ hydrogen or an organic radical selected from an alkyl group or alkenyl group, an aryl or aralkyl group in which the alkyl or alkenyl groups contain up to 32 carbon atoms and the aryl or aralkyl groups are selected from benzene and naphthalene groups which contain up to 15 carbon atoms each.

2. The compound of claim 1 wherein R⁶ and R⁷ are n-butyl and R, R¹, R², R³, R⁴ and R⁵ are hydrogen.

3. The compound of claim 1 wherein R⁶ and R⁷ are n-butyl, R, R², R⁴ and R⁵ are hydrogen and R¹ and R³ taken together form the group --CH₂ CH═

CH--.

4. The compound of claim 1 wherein R⁶ and R⁷ are isopropyl, R, R¹, R², R⁴ and R⁵ are hydrogen and R³ is --CH═

CH₂.