DE1594389A1 - Mineral or synthetic lubricating oil - Google Patents

Description

PATENT LAWYERS "· 159 Λ 3

DR. W. SCHALK DIPL.-ING.P. WlRTH DIPL.-ING.G. DANNENBERG

dr.v. schmied-Kowarzik · dr.p.Weinhold

6 FRANKFURT AM MAIN

OR. ESCHENHEIMER STR. 30th

SK / Dt / Kl ( D 45 914

' BA 484o2 / 65

The Distillers Company Limited 12, Torphichen Street Edinburgh J, UK

Mineral or synthetic lubricating oil *

The invention relates to a mineral or synthetic Lubricating oil containing an amine compound as an antioxidant.

Antioxidants for synthetic lubricating oils are already known that have the general formula

(R ^l O) _n -Ar-EH-AE · - (OB ") _n

where Ar represents a benzene or naphthalene nucleus and both nuclei can have alkyl substituents, Ä ¹ and H "are saturated alkyl radicals which contain a total of 8 to Zq KohXeastoffatoaie, m 1 or 2 and η» 0 or 1 1st *

Bias® Alfeoxyanine 1 @ 0® © e aieli sEsr TUBAt & ullieh from:
© äßig sohw® ^ euir. '73 ^ fUgUi ^ st © Ji # »dea. ttfttea? iaX.le & feaw »

BATH ORIGINAL

Manufacture raw materials. Step into the manufacturing process often undesirable weaving reactions. In addition, there are "cleaning stages required so that the yield does not have the desired level. The known antioxidants also have only one protonic hydrogen atom suitable for delivery to molecule.

New antioxidants have now been found, the two protonic ones Can give off hydrogen atoms per molecule o

The subject of the invention is a mineral or synthetic lubricating oil ₉ which is characterized in that it contains at least one substituted 2-oxyphenylamine of the formula

■ MB - X

in which X is a phenyl, a Maphthy.1-, a biphenyl or · a phenyl radical substituted by alkyl, alkoxy or halogen or a radical of the formula

1 © ia AffgrXes- od » DipheaylErotfc & ^ & s ^ is mat H and

and Äi

sj ^ ljb

bad original ^

The "positions on the aromatic compounds included in the above Formulas shown unsubstituted can optionally be substituted by further substituents, such as alkyl groups or H ^ xogen atoms be"

According to one embodiment of the invention, that represented by T is group a p-phenylene group, a m-tolylene group, a p-xylylene group, a group of the formula:

or a group of the formula:

In a preferred embodiment of the invention, the Group X has the formula:

- ■ '■ · Z ■■■■

where E stands for an alkyl group, an alkyoxy group or a halogen atom, such as a methyl group, an ethoxy group, or a Chlorine atom.

E and E are expediently tcrt.-butyl, cC-methylbenzyl or <£, X-dimethylbenzyl.

_{ÖA (} , "9830/1991 BAU ORIGINAL

As "special compounds according to the invention in lubricant preparations used as antioxidants, there can be mentioned, for example, the following:

3,5-di-tert. -butyl ^ -oxy- ^ '-me thyldiphenylamine, 3 j 5-di-tert. - "butyl-2-OKy-4 '-chlardiphenylamine, 3,5-di-tert. -butyl-2-oxy-4'-ethoxydiphenylamine,

If, N '-Di- (3,5-di-tert-butyl-2-oxyphenyl) -o-phenylendiamine,

the compounds of the formula:

HO

where E stands for tert-butyl.

The boiling agent base may, for example, be a hydrocarbon oil of the type. in crankcase oil formulations for Internal combustion engines is used. The lubricant base material can also be a synthetic lubricant, e.g. an '' ■ alkyl ester of an aliphatic dicarboxylic acid, e.g. dioctyl sebacate, or a lubricant base stock of the type described in US Pat

British patent application Mr. 46968/63 of 28 * 11.1963 in

Germany with application from 24 ·. 11.1964 deposited, described

The lubricant preparations according to the invention can continue to Additives such as corrosion inhibitors, agents for improving the

0098307 1991 " ⁵ "

BATH ORIGINAL

.- "■ - 5 - ■ ■ ■

Viscosity index, means for reducing the pour point, dispersing agent and cleaning agents. Some of the substituted 2-oxyphenylamines mentioned above are new connections.

The invention also provides substituted 2-oxyphenylamines the formula:

"E ¹ OH HO E ¹

-ME-Y-KH-

1 2 ■ ".- ■ '.

in which Y, E and E have the above meaning.

The novel compounds according to the invention can be prepared are produced by the condensation of a 2,5-disubstituted pyrocate

chins of the formula;

OH

E '
with an aromatic diamine of the formula HpN.YM ₂ »where E,

2 ■ "'" ■■■ ■

R and Y have the above meaning ». ^

The other methods suitable according to the invention can be prepared are 3 »5 ~ disubstituted by condensation Pyrocatechins of the formulaί

W OH

OH

alt an aromatic amine the formula HpIi-Z, in which Z stands for eheayl3? @st, a Kaphthylreet, a Biphenylrest or © inea with alkyl, Jklkoxar''od®z> Salog «a ufeitltuierten bienylrest

The general method for making these "compounds" is to dissolve the Jj ^ -disubstituted catechol in Light petroleum and, in addition, the solution to a solution of the aromatic amine compound in light petroleum. As a catalyst a few drops of trimethylamine are added and the mixture left to stand for a few hours, the product separates a substituted 2-oxyphenylamine, which is filtered off, with Ligroin can be waxed and kneaded »

The detection is illustrated in the following examples.

example 1

According to ASTM test method D 972-56, preparations made from Dinonyl sebacate with various "known antioxidants" passed, tested for their resistance to oxidation, the test being carried out in a glass device at 26o °. These results are contrasted with the results obtained by means of the new Compounds of the formula

have been received

BADORiGfNAL

Tabel

Ant ioxidation agent

Appearance by weight, loss of test

1. no means

2. 0.5 % phenothiazine

5. 0.5% 3,7-dioctylphenothiazine

B) substituted 2-oxyphenylamine R ⁵ = methyl)

0.5 % (fi ¹ -E ² «tert. butyl;

. 5 ρ ο, 5 ° / o (R ^ = R = tert-butyl;

R ⁵ == chlorine) 6.0.5% (R ¹ -R ² = tert-butyl;

R ⁵ = ethoxy)

very dark, heavy sc hl amm-u. Lacquer formation very dark, heavy sludge and varnish formation darkened, slight varnish formation

34- darkened, light Lacquer formation

darkened, slight varnish formation

darkened, some lacquer formation

Instead of dinonyl sebacate, dioctyl sebacate, dipentaerythritol tricaprylate tributyrate was used (P.C.B.) »the octyl tetraester of cyelohexanone-2,2,6,6-tetrakis- (ß-propionic acid) (CHTP) or a Mixture of 55 parts of the 2-ethylhexyl tetraester of cyclohexanone-2,2,6,6-tetrakis- (ß-propionic acid) used with 45 parts of dinonyl sebacate, similar results were obtained.

Example 2

Example! Was repeated, however, new compounds of the

Type

009830/1991 ORIGINAL BATHROOM

- 8 were used.

Act 2

Antioxidant weight loss in %

A) "known

1. none; 79

2o o _t 3% dioctylphenothiazine 59

3. o, 5 ° / o phenothiazine 7o

B) substituted 2-oxyphenylamine A. 0.5 % (R ¹ «E ² » tert-butyl;

^J 54.2

5. ο, $ 5 (R '= R ^ etert.Butyl j

Example 3 *

Preparations from a lubricating oil base and various known ones and new antioxidants were pettered in a standard W 1 Motor test tested for resistance to oxidation and bearing corrosion. The results are in the table. 3 indicated that too similar results for the lube base without stabilizer as well as the accepted rating for lubricating oils.

The stabilizing agent used in the present invention possessed the

OH

009830/1991 ORIGINAL BATHROOM

οοοοω

IA O O LTv

οο

co

f4 Φ 50 -HLfN

OH D-

O IA CT »C \ J CVJ H

O H

■ Μ

i§iSIÖ /! tl1 BADOR ₁ G ₁ NAL

- lo-

Example 4-

Preparations which consisted of a lubricating oil base (containing cleaning agents and alkaline additives) with various "known and new antioxidants" were tested for corrosion and the formation of volatile acids in a laboratory copper-lead bearing corrosion test. The results are given in Table 4, which also contains similar results for the lubricating oil base with no stabilizer. The values for the coking rating are arbitrary units from 0 ("new") to 7 (complete coking "), 0 to 3 are useful values _e

The new gxyphenylamines correspond to the formula

// \ y_my

for a)

for B)

- 10 »-

.30

Table 4

Antioxidants

S—

ST known

Concentr. Start d. Corrosion, corrosion, coking
% Corrosion speed sion n. ge acids rating
in hours mg / hour 18 hours in milli-

mol loog

none / ^ n -

Ethyl 702> '< o, 25

ethyl 736 ^ ^; o, 15

substituted 2-oxyphenylamine

A) R ¹ = R ² * tert-butyl ° » ⁴ 5 X« p-tolyl

B) R ^ eR ^ tert-butyl o, 3o

more than
17th

5o

34
39

542 137 325

6o

21.3

more than

35 16.1

29.9

8.7

7.9

(1) and (2) see table

cn CO 4> CO OO CO

Claims (2)

Claims 1. Mineral or synthetic lubricating oil, thus identified - indicates that there is at least one substituted 2-oxyphenylamine the formula? OH -EH - X in which X is a phenyl, a liaphthyl, a biphenyl or a phenyl radical substituted by alkyl, alkoxy or halogen or an Eest of the formula 1, where Y is an arylene or diphenylmethane radical and E is and E are identical or different and denote alkyl, aryl, alkenyl or aralkenyl radicals ". 2. 2-oxyphenylamine of the general formula L ₁ sentence 3 of the amendment ^ V. BATH ORIGINAL 3 * 2 ~ oxyphenylamine according to claim. 2, characterized in that that in the formula
R OH HO R-. -KE- -HH- S a .tert. - Means butyl radical. 4 ·. 2-Oxyph.enylamine according to Claim 2, characterized in that in the normal
E QH ■ ÜH- SQ E r-m- E means a tert-butyl radical. 5 · 2-oxyphenylamine according to claim 2, characterized in that in the formula.
K OH ^ HO ' E means a tert-butyl radical. The patent attorney 009830/1991