Additive for lubricant or fuel, lubricating oil composition or fuel composition containing it, and substituted hydroxyaromatic ester derivative

• US 5,686,398 A
• Filed: 12/06/1995
• Issued: 11/11/1997
• Est. Priority Date: 06/15/1993
• Status: Expired due to Term

• Current Assignee: Idemitsu Kosan Company Limited
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: Ikeda, Harutomo, Minokami, Tomiyasu, Gotoh, Masahisa, Koshima, Hiroaki
• Primary Examiner(s): McAvoy, Ellen M.
• Application Number:
  US08/557,103
• Time in Patent Office: 706 Days
• Field of Search: 508/502, 508/480, 508/481, 508/483, 44/389, 44/400
• US Class Current: 508/481
• CPC Class Codes: C07C 69/88 with esterified carboxyl groups
• CPC Class Codes: C07C 69/94 of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C10L 1/143 mixtures of organic macromolecular compounds with organic non-macromolecular compounds
• CPC Class Codes: C10L 1/1817 Compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• CPC Class Codes: C10L 1/19 Esters ester radical containing compounds; ester ethers; carbonic acid esters C10L1/1802, C10L1/1805, C10L1/1808, C10L1/1811, C10L1/1814, C10L1/1817 take precedence
• CPC Class Codes: C10L 1/1905 of di- or polycarboxylic acids
• CPC Class Codes: C10L 1/191 of di- or polyhydroxyalcohols
• CPC Class Codes: C10L 1/198 obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
• CPC Class Codes: C10L 1/1985 polyethers, e.g. di- polygylcols and derivatives; ethers - esters
• CPC Class Codes: C10L 1/201 aliphatic bond
• CPC Class Codes: C10L 1/202 aromatic bond
• CPC Class Codes: C10L 1/205 carboxylic radical containing compounds or derivatives, e.g. salts, esters
• CPC Class Codes: C10L 1/208 containing halogen, oxygen, with or without hydrogen
• CPC Class Codes: C10L 1/221 compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• CPC Class Codes: C10L 1/2225 hydroxy containing C10L1/221 takes precedence
• CPC Class Codes: C10L 1/224 Amides; Imides carboxylic acid amides, imides C10L1/221, C10L1/2227 take precedence
• CPC Class Codes: C10L 1/231 nitro compounds; nitrates; nitrites C10L1/221 takes precedence
• CPC Class Codes: C10L 1/238 obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds C10L1/221 takes precedence
• CPC Class Codes: C10L 1/2383 Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C) C10L1/221 takes precedence
• CPC Class Codes: C10L 1/2387 Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C) C10L1/221 takes precedence
• CPC Class Codes: C10L 1/2418 : containing a carboxylic substituted; derivatives thereof, e.g. esters
• CPC Class Codes: C10L 1/2475 : obtained otherwise than by reactions only involving unsaturated carbon to carbon bonds
• CPC Class Codes: C10L 1/2493 : compounds of uncertain formula; reactions of organic compounds (hydrocarbons, acids, esters) with sulfur or sulfur containing compounds
• CPC Class Codes: C10L 1/2691 : Compounds of uncertain formula; reaction of organic compounds (hydrocarbons acids, esters) with Px Sy, Px Sy Halz or sulfur and phosphorus containing compounds
• CPC Class Codes: C10L 1/303 : boron compounds
• CPC Class Codes: C10L 1/305 : organo-metallic compounds (containing a metal to carbon bond)
• CPC Class Codes: C10L 10/02 : for reducing smoke development
• CPC Class Codes: C10L 10/04 : for minimising corrosion or incrustation
• CPC Class Codes: C10L 10/08 : for improving lubricity; for reducing wear
• CPC Class Codes: C10M 129/76 : containing free hydroxy or carboxyl groups
• CPC Class Codes: C10M 145/22 : Polyesters
• CPC Class Codes: C10M 2207/14 : having carboxyl groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C10M 2207/142 : polycarboxylic
• CPC Class Codes: C10M 2207/282 : of (cyclo)aliphatic oolycarboxylic acids
• CPC Class Codes: C10M 2207/284 : of aromatic monocarboxylic acids
• CPC Class Codes: C10M 2207/285 : of aromatic polycarboxylic acids
• CPC Class Codes: C10M 2207/287 : Partial esters
• CPC Class Codes: C10M 2207/34 : Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
• CPC Class Codes: C10M 2209/102 : Polyesters
• CPC Class Codes: C10M 2227/061 : Esters derived from boron
• CPC Class Codes: C10N 2040/25 : Internal-combustion engines
• CPC Class Codes: C10N 2040/251 : Alcohol-fuelled engines
• CPC Class Codes: C10N 2040/255 : Gasoline engines
• CPC Class Codes: C10N 2040/28 : Rotary engines
• CPC Class Codes: F02B 3/06 : with compression ignition compression ignition engines using air or gas for blowing fuel into compressed air in cylinder F02B13/02

Abstract

There are herein disclosed an additive for a lubricant or a fuel which comprises at least one selected from the group consisting of substituted hydroxyaromatic ester derivatives represented by the general formulae (I) and (II) ##STR1## wherein R¹ to R⁵ are each an organic group having 6 or more carbon atoms, a, b, d, e, k and m are from 1 to 3, c, f, g, i and j are from 0 to 3, and h is from 0 to 4, but (f+g) is from 1 to 3, and (h+i) is from 1 to 6, an additive composition for a lubricant or a fuel, and a lubricating oil composition or a fuel composition containing the above-mentioned additive.

The above-mentioned additive for the lubricant or the fuel is desirable as an ashless detergent excellent in high-temperature stability in place of a metal detergent, and the lubricating oil composition or the fuel composition containing this additive can suitably be used as the lubricant or the fuel for an internal combustion engine which can comply with future exhaust gas controls.

Claims

1. An additive for a lubricant comprising at least one selected from the group consisting of substituted hydroxyaromatic ester derivatives represented by the general formula (I) ##STR40## wherein R¹ and R² are each an organic group having 6 or more carbon atoms, and they may be the same or different;

a, b, c, d and e are integers satisfying the relations of 1≦

a≦

3, 1≦

b≦

3, 0≦

c≦

3, 1≦

d≦

3, 1≦

e≦

3, 3≦

(a+b+e)≦

6 and 1≦

(c+d)≦

5, respectively; and

when a plurality of R¹ s and R² s are present, they may be the same or different, and the general formula (II) ##STR41## wherein R³, R⁴ and R⁵ are each an organic group having 6 or more carbon atoms, and they may be the same or different;

f, g, h, i, j, k and m are integers satisfying the relations of 0≦

f≦

3, 0≦

g≦

3, 1≦

(f+g)≦

3, 0≦

h≦

4, 0≦

i≦

3, 1≦

(h+i)≦

6, 0≦

j≦

3, 1≦

k≦

3, 1≦

m≦

3, 3≦

(f+g+h+i+m)≦

8 and 1≦

(j+K)≦

5, respectively; and

when a plurality of R³ s, R⁴ s and R⁵ s are present, they may be the same or different.

2. The additive for a lubricant according to claim 1 wherein the substituted hydroxyaromatic ester derivative is represented by the general formula (III) ##STR42## wherein R¹ and R² are each an organic group having 6 or more carbon atom, and they may be the same or different;

b, d and e are integers satisfying the relations of 1≦

b≦

3, 1≦

d≦

3, 1≦

e≦

3 and 2≦

(b+e)≦

5, respectively; and

when a plurality of R¹ s and R² s are present, they may be the same or different, or the general formula (III'"'"') ##STR43## wherein R³, R⁴ and R⁵ are each an organic group having 6 or more carbon atoms, and they may be the same or different;

h, n, k and m are integers satisfying the relations of 0≦

h≦

4, 0≦

n≦

2, 1≦

(h+n)≦

6, 1≦

k≦

3, 1≦

m≦

3 and 2≦

(h+n+m)≦

7, respectively; and

when a plurality of R³ s, R⁴ s and R⁵ s are present, they may be the same or different.

3. An additive composition for a lubricant which comprises (a) said additive according to claim 1 which includes said at least one selected from substituted hydroxyaromatic ester derivatives represented by the general formulae (I) and (II), and (b) an ashless dispersant.

4. An additive composition for a lubricant which comprises (a) said additive according to claim 2 which includes at least one selected from the substituted hydroxyaromatic ester derivatives represented by the general formulae (III) and (III'"'"') and an ashless dispersant.

5. A lubricant composition which is obtained by adding, to a base oil for a lubricating oil, said additive according to claim 1 which includes said at least one selected from substituted hydroxyaromatic ester derivatives represented by the general formulae (I) and (II).

6. A lubricant composition which is obtained by adding, to a base oil for a lubricant, (a) said additive according to claim 1 which includes said at least one selected from substituted hydroxyaromatic ester derivatives represented by the general formulae (I) and (II), and (b) an ashless dispersant.

7. The lubricant composition according to claim 5 or 6 which is a lubricating oil composition for an internal combustion engine.

8. A lubricant composition which is obtained by adding, to a base oil for a lubricating oil, said additive according to claim 2 which includes said at least one selected from the substituted hydroxyaromatic ester derivatives represented by the general formulae (III) and (III'"'"').

9. A lubricant composition which is obtained by adding, to a base oil for a lubricating oil, (a) said additive according to claim 2 which includes said at least one selected from the substituted hydroxyaromatic ester derivatives represented by the general formulae (III) and (III'"'"'), and (b) an ashless dispersant.

10. The additive for a lubricant according to claim 1, including at least one selected from the group consisting of substituted hydroxyaromatic esters represented by the general formula (II).

11. The additive for a lubricant according to claim 2, wherein the substituted hydroxyaromatic ester derivative is represented by the general formula (III'"'"').

12. An additive composition for a lubricant which comprises (a) said additive according to claim 10 or 11, and (b) an ashless dispersant.

13. A lubricant composition for a lubricant which is obtained by adding, to a base oil for a lubricant, said additive according to claim 10 or 11.

14. A lubricant composition for a lubricant which is obtained by adding, to a base oil for a lubricant, (a) said additive according to claim 10 or 11, and (b) an ashless dispersant.

15. An additive for a fuel which comprises at least one selected from the group consisting of substituted hydroxyaromatic ester derivatives represented by the general formula (I) ##STR44## wherein R¹ and R² are each an organic group having 6 or more carbon atoms, and they may be the same or different;

a, b, c, d and e are integers satisfying the relations of 1≦

a≦

3, 1≦

b≦

3, 0≦

c≦

3, 1≦

d≦

3, 1≦

e≦

3, 3≦

(a+b+e)≦

6 and 1≦

(c+d)≦

5, respectively; and

when a plurality of R¹ s and R² s are present, they may be the same or different, and the general formula (II) ##STR45## wherein R³, R⁴ and R⁵ are each an organic group having 6 or more carbon atoms, and they may be the same or different;

f, g, h, i, j, k and m are integers satisfying the relations of 0≦

f≦

3, 0≦

g≦

3, 1≦

(f+g)≦

3, 0≦

h≦

4, 0≦

i≦

3, 1≦

(h+i)≦

6, 0≦

j≦

3, 1≦

k≦

3, 1≦

m≦

3, 3≦

(f+g+h+i+m)≦

8 and 1≦

(j+K)≦

5, respectively; and

when a plurality of R³ s, R⁴ s and R⁵ s are present, they may be the same or different.

16. The additive for a fuel according to claim 15 wherein the substituted hydroxyaromatic ester derivative represented by the general formula (III) ##STR46## wherein R¹ and R² are each an organic group having 6 or more carbon atoms, and they may be the same or different;

b, d and e are integers satisfying the relations of 1≦

b≦

3, 1≦

d≦

3, 1≦

e≦

3 and 2≦

(b+e)≦

5, respectively; and

when a plurality of R¹ s and R² s are present, they may be the same or different, or the general formula (III'"'"') ##STR47## wherein R³, R⁴ and R⁵ are each an organic group having 6 or more carbon atoms, and they may be the same or different;

h, n, k and m are integers satisfying the relations of 0≦

h≦

4, 0≦

n≦

2, 1≦

(h+n)≦

6, 1≦

k≦

3, 1≦

m≦

3 and 2≦

(h+n+m)≦

7, respectively; and

when a plurality of R³ s, R⁴ s and R⁵ s are present, they may be the same or different.

17. An additive composition for a fuel which comprises (a) said additive according to claim 15 which includes said at least one selected from substituted hydroxyaromatic ester derivatives represented by the general formulae (I) and (II), and (b) an ashless dispersant.

18. An additive composition for a fuel which comprises (a) said additive according to claim 16 which includes at least one selected from the substituted hydroxyaromatic ester derivatives represented by the general formula (III) add (III'"'"'), and (b) an ashless dispersant.

19. A fuel composition which is obtained by adding, to a fuel, said additive according to claim 15 which includes said at least one selected from substituted hydroxyaromatic ester derivatives represented by the general formulae (I) and (II).

20. A fuel composition which is obtained by adding, to a fuel, (a) said additive according to claim 15 which includes said at least one selected from substituted hydroxyaromatic ester derivatives represented by the general formulae (I) and (II), and (b) an ashless dispersant.

21. The fuel composition according to claim 19 or 20 which is a fuel composition for an internal combustion engine.

22. A fuel composition which is obtained by adding, to a fuel, said additive according to claim 16 which includes said at least one selected from the substituted hydroxyaromatic ester derivatives represented by the general formulae (III) and (III'"'"').

23. A fuel composition which is obtained by adding, to a fuel, (a) said additive according to claim 16 which includes said at least one selected from the substituted hydroxyaromatic ester derivatives represented by the general formulae (III) and (III'"'"'), and (b) an ashless dispersant.

24. The additive for a fuel according to claim 15, including at least one selected from the group consisting of substituted hydroxyaromatic esters represented by the general formula (II).

25. The additive for a fuel according to claim 16, wherein the substituted hydroxyaromatic ester derivative is represented by the general formula (III'"'"').

26. An additive composition for a fuel which comprises (a) said additive according to claim 24 or 25 and (b) an ashless dispersant.

27. A fuel composition which is obtained by adding, to a fuel, said additive according to claim 24 or 25.

28. A fuel composition which is obtained by adding, to a fuel, (a) said additive according to claim 24 or 25, and (b) an ashless dispersant.

29. A substituted hydroxyaromatic ester derivative represented by the general formula (IV) ##STR48## wherein R⁶ and R⁷ are each an alkyl group having 9 to 20 carbon atoms, and they may be the same or different.

30. A process for preparing a substituted hydroxyaromatic ester derivative described in claim 29 which comprises the step of reacting an alkyl group-substituted salicylic acid represented by the general formula (V) ##STR49## wherein R⁶ is an alkyl group having 9 to 20 carbon atoms, with an alkyl-substituted phenol represented by the general formula (VI) ##STR50## wherein R⁷ is an alkyl group having 9 to 20 carbon atoms, in the presence of no catalyst or a catalyst.

31. A substituted hydroxyaromatic ester derivative represented by the general formula (VII) ##STR51## wherein R⁸, R⁹ and R¹⁰ are each a hydrocarbon group, and they may be the same or different.

32. The substituted hydroxyaromatic ester derivative according to claims 31 wherein R⁸ of the general formula (VII) is an alkyl group.

33. A process for preparing a substituted hydroxyaromatic ester derivative described in claim 31 which comprises the step of reacting a hydrocarbon group-substituted hydroxybenzenedicarboxylic acid represented by the general formula (VIII) ##STR52## wherein R⁸ is a hydrocarbon group, with at least one of hydrocarbon group-substituted phenols represented by the general formula (IX) ##STR53## wherein R¹¹ is R⁹ or R¹⁰, and it is a hydrocarbon group, in the presence of no catalyst or a catalyst.

34. The process for preparing a substituted hydroxyaromatic ester derivative according to claim 33 wherein R⁸ of the general formula (VIII) is an alkyl group.