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Patent 2650246 Summary

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(12) Patent: (11) CA 2650246
(54) English Title: CORROSION INHIBITING COMPOSITION FOR NON-FERROUS METALS
(54) French Title: COMPOSITION INHIBANT LA CORROSION POUR METAUX NON-FERREUX
Status: Deemed expired
Bibliographic Data
(51) International Patent Classification (IPC):
  • C10M 141/10 (2006.01)
  • C10M 161/00 (2006.01)
(72) Inventors :
  • MICHEL, KARL-HEINZ (Germany)
  • NEHLS, ERIC (Germany)
  • HABEREDER, TASSILO (Germany)
  • KELLER, ANJA (Germany)
(73) Owners :
  • CIBA HOLDING INC. (Switzerland)
(71) Applicants :
  • CIBA HOLDING INC. (Switzerland)
(74) Agent: FETHERSTONHAUGH & CO.
(74) Associate agent:
(45) Issued: 2014-12-23
(86) PCT Filing Date: 2007-05-15
(87) Open to Public Inspection: 2007-11-29
Examination requested: 2012-05-14
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/EP2007/054674
(87) International Publication Number: WO2007/135017
(85) National Entry: 2008-10-23

(30) Application Priority Data:
Application No. Country/Territory Date
06114370.7 European Patent Office (EPO) 2006-05-23

Abstracts

English Abstract

The invention relates an additive composition for use as a metal working fluid and a process for protection of metals, particularly zinc or aluminum, against corrosion or oxidative degradation. The composition comprises an additive mixture of an alkenyl succinic half ester, a substituted imidazoline compound and amine phosphate partial ester in a functional fluid.


French Abstract

La présente invention concerne une composition additive pour une utilisation en tant que fluide de travail de métaux et un procédé pour protéger les métaux, en particulier le zinc ou l'aluminium, contre la corrosion ou la dégradation oxydante. La composition comprend un mélange additif d'un semi-ester d'acide alcénylsuccinique, d'un composé imidazoline substitué et d'un ester partiel d'aminophosphate dans un fluide fonctionnel.

Claims

Note: Claims are shown in the official language in which they were submitted.



-20-

CLAIMS:

1. A composition, which comprises
A) an additive mixture that consists of
a) at least one alkenyl succinic half ester of the formula
Image
wherein R1 represents C6-C18alkenyl, R2 represents hydrogen or methyl and n is
a
numeral from 1 to 100;
b) at least one imidazoline compound of the formula
Image
wherein one of R1 and R2 represents hydrogen and the other one represents a
substituent selected from the group consisting of C1-C12alkyl, hydroxy-C2-
C12alkyl,
amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl
and
C1-C4alkylphenyl-C1-C4alkyl; or
wherein both of R1 and R2 represent substituents selected from the group
consisting
of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl,
phenyl-
C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl; and
c) at least one amine phosphate partial ester of the formula


-21-

Image
wherein m represents 1 or 2;
n represents 2, if m represents 1, or represents 1, if m represents 2;
R represents a substituent selected from the group consisting of C1-C12alkyl,
hydroxy-
C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl,
C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl,
C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl; and
R a, R b, R c and R d independently of one another represent hydrogen or a
substituent
selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-
C2-C12alkyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-
C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-C4-
C8cycloalkyl
and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl; and
B) a functional fluid.
2. A composition according to claim 1, which comprises
A) an additive mixture that consists of
a) at least one alkenyl succinic half ester (I), wherein
R1 represents C10-C16alkenyl, R2 represents methyl and n is a numeral from 1
to 20;
b) at least one imidazoline compound (II),
wherein one of R1 and R2 represents hydrogen and the other one represents a
substituent selected from the group consisting of C1-C12alkyl, hydroxy-C2-
C12alkyl,
amino-C2-C12alkyl and C12-C18alkenyl; or


-22-

wherein both of R1 and R2 represent substituents selected from the group
consisting
of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl and C12-C18alkenyl; and
c) at least one amine phosphate partial ester (III),
wherein m represents 1 or 2;
n represents 2, if m represents 1, or represents 1, if m represents 2;
R represents a substituent selected from the group consisting of C1-C12alkyl,
hydroxy-C2-C12alkyl and amino-C2-C12alkyl; and
R a, R b, R c and R d independently of one another represent hydrogen or a
substituent
selected from the group consisting of C1-C12alkyl and hydroxy-C2-C12alkyl; and
B) a functional fluid.
3. A composition according to claim 1, which comprises
A) an additive mixture that consists of
a) at least one alkenyl succinic half ester (I), wherein
R1 represents C12-C16alkenyl, R2 represents methyl and n is a numeral from 1
to 20;
b) at least one imidazoline compound (II),
wherein one of R1 and R2 represents hydrogen and the other one represents a
substituent selected from the group consisting of C1-C12alkyl and C12-
C18alkenyl; or
wherein both of R1 and R2 represent substituents selected from the group
consisting
of C1-C12alkyl and C12-C18alkenyl; and
c) at least one amine phosphate partial ester (III),
wherein m represents 1 or 2;


-23-

n represents 2 if m represents 1; or
represents 1 if m represents 2; and
R represents a substituent selected from the group consisting of C1-C12alkyl
and
hydroxy-C2-C12alkyl; and
R a, R b, R c and R d independently of one another represent hydrogen or a
substituent
selected from the group consisting of C1-C12alkyl and hydroxy-C2-C12alkyl; and
B) a functional fluid.
4. A composition, which comprises
a) at least one alkenyl succinic half ester (I),
Image
wherein R1 represents C6-C18alkenyl, R2 represents methyl and n is a numeral
from 1 to 100;
b) at least one imidazoline compound (II),
Image
wherein one of R1 and R2 represents hydrogen and the other one represents a
substituent selected from the group consisting of C1-C12alkyl, hydroxy-C2-
C12alkyl,
amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl
and
C1-C4alkylphenyl-C1-C4alkyl; or


-24-

wherein both of R1 and R2 represent substituents selected from the group
consisting
of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl,

phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl;
c) at least one amine phosphate partial ester (III),
Image
wherein m represents 1 or 2;
n represents 2 if m represents 1; or
represents 1 if m represents 2; and
R represents a substituent selected from the group consisting of C1-C12alkyl,
hydroxy-
C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl,
C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-
C4alkyl-
C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl; and
R a, R b, R c and R d independently of one another represent hydrogen or a
substituent
selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-
C2-C12alkyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-
C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-C4-
C8cycloalkyl
and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl; and
d) additives.
5. An additive mixture that consists of
a) at least one alkenyl succinic half ester (I),


-25-

Image
wherein R1 represents C6-C18alkenyl, R2 represents hydrogen or methyl and n is
a
numeral from 1 to 100;
b) at least one imidazoline compound (II),
Image
wherein one of R1 and R2 represents hydrogen and the other one represents a
substituent selected from the group consisting of C1-C12alkyl, hydroxy-C2-
C12alkyl,
amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl
and
C1-C4alkylphenyl-C1-C4alkyl; or
wherein both of R1 and R2 represent substituents selected from the group
consisting
of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl,
phenyl-
C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-C1-C4alkyl; and
c) at least one amine phosphate partial ester (Ill),
Image
wherein m represents 1 or 2;
n represents 2 if m represents 1; or
represents 1 if m represents 2; and


-26-

R represents a substituent selected from the group consisting of C1-C12alkyl,
hydroxy-
C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl,
C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-
C8cycloalkyl-
C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-
C4alkyl; and
R a, R b, R c and R d independently of one another represent hydrogen or a
substituent
selected from the group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-
C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl,
C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-
C4alkyl-
C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl.
6. A composition according to claim 1, wherein the functional fluid B) is a

non-aqueous functional liquid selected from the group consisting of
lubricants,
hydraulic fluids, metal working fluids, engine coolants, transformer oils and
switch
gear oils.
7. A process for protection against corrosion or oxidative degradation of
metals, wherein the metal is exposed to a functional fluid comprising the
additive
mixture according to claim 5.
8. A process for protection against corrosion or oxidative degradation of
zinc, aluminum or alloys thereof, or zinc-coated steels, wherein zinc,
aluminum or
alloys thereof are exposed to a functional fluid comprising the additive
mixture
according to claim 5.

Description

Note: Descriptions are shown in the official language in which they were submitted.


CA 02650246 2008-10-23
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- 1 -
CORROSION INHIBITING COMPOSITION FOR NON-FERROUS METALS
The invention relates to an additive composition for use as a metal working
fluid or corrosion
protection oil and a process for the protection of metals, particularly zinc
or aluminium alloys,
against corrosion or oxidative degradation.
Additives, which have the purpose to protect metals against corrosion are
commonly divided
in to two classes:
Metal deactivators are used to protect yellow metals or alloys, such as copper
or brass, and
display their protective action in functional liquids, such as mineral oil or
fuels, by deactivat-
ing the metal ions contained therein. These metal ions can have catalytic
effects in undesired
oxidative decomposition processes of mineral oil or fuels. The protective
action is explained
by the formation of film-like layers on the surface of metals or by complex
formation with
metal ions.
Corrosion inhibitors are primary used to protect ferrous metals such as iron
or steel. Ana-
logue to metal deactivators, corrosion inhibitors, are forming also film-like
layers on the sur-
face of metals. In addition some corrosion inhibitors can prevent the
corrosion, by emulsify-
ing water and minimizing therefore the direct contact of water with the metal
surface.
Presently metal protection methods focus primarily on iron and copper
surfaces. However,
other metals, such as zinc and aluminium and their related alloys, have become
very impor-
tant in many technical applications. Zinc and aluminium are, for example,
widely used in the
manufacture of automobiles. Zinc is widely used as corrosion protection
coating of steels,
e.g. zinc coated steel coils. Corrosion problems often occur during transport,
handling and
working of semi-finished metal products. Unfortunately, presently used metal
deactivator
compositions are less satisfactory or even unsatisfactory to protect these
metal surfaces.
Therefore, there is a clear need for improved metal working fluids to prevent
corrosion of
these metals
British Patent Specification No. 795,491 discloses the preparation of alkenyl
succinic half
esters and their applicability as steam turbine lubricant additives.
British Patent Specification No. 1,043,488 lubricating oil compositions
comprising substituted
imidazoline compounds and phosphate partial esters.
U.S. Patent Application Publication No. 2005/0272614 discloses corrosion
inhibiting compo-
sitions, wherein substituted imidazolines and neutral metal sulfonate
corrosion inhibitors are
present.

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- 2 -
It has surprisingly been found that mixtures of alkenyl succinic half esters,
substituted imida-
zoline compounds and amine phosphate partial esters in functional fluids, such
as oils, pre-
vent the corrosion of zinc, zinc coated steel and aluminum metal samples. This
anticorrosive
effect can be increased by the further admixture of additional anti-corrosive
agents, such as
substituted imidazolines and amine phosphate partial esters.
The present invention relates to a composition, which comprises
A) An additive mixture that essentially consists of
a) At least one alkenyl succinic half ester of the formula
H
R1¨?- CO -OH
H
CHCO-04¨CHC-0+H (I),
I n
R2
Wherein R1 represents C6-C18alkenyl, R2 represents hydrogen or methyl and n is
a
numeral from 1 to 100;
b) At least one imidazoline compound of the formula
/--\
N,,, kl-R2 (II),
1
R1
Wherein one of R1 and R2 represents hydrogen and the other one represents a
substituent selected from the group consisting of C1-C12alkyl, hydroxy-C2-
C12alkyl,
amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1atalkyl, Cratalkylphenyl
and C1atalkylphenyl-Cratalkyl; or
Wherein both of R1 and R2 represent substituents selected from the group con-
sisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl,
phenyl, phenyl-C1atalkyl, Cratalkylphenyl and C1atalkylphenyl-Cratalkyl; and
c) At least one amine phosphate partial ester of the formula
¨ Ra ¨
0 I
I I R N + (III),
P (1
1 R,
(RO)r,/ "(0) Rc -
_ n
Wherein m represents 1 or 2;
n represents 2, if m represents 1, or represents 1, if m represents 2;

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- 3 -
R represents a substituent selected from the group consisting of CrCualkyl, hy-

droxy-C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-C1atalkyl,
Cratalkylphenyl, C1atalkylphenyl-Cratalkyl, a4-C8cycloalkyl, a4-C8cyclo-
alkyl-C1-a4alkyl, C1-a4alkyl-C4-C8cycloalkyl and C1-a4alkyl-C4-C8cyclo-
alkyl-C1atalkyl; and
Ra, Rb, Rc and Rd independently of one another represent hydrogen or a
substitu-
ent selected from the group consisting of CrCualkyl, hydroxy-C2-C12alkyl,
amino-C2-C12alkyl, phenyl, phenyl-C1atalkyl, Cratalkylphenyl,
C1atalkylphenyl-Cratalkyl, a4-C8cycloalkyl, a4-C8cycloalkyl-C1-a4alkyl,
C1-a4alkyl-C4-C8cycloalkyl and C1-a4alkyl-C4-C8cycloalkyl-C1-a4alkyl; and
B) A functional fluid.
A preferred embodiment of the invention relates to a composition, which
comprises
A) An additive mixture that essentially consists of
a) At least one alkenyl succinic half ester (I), wherein
R1 represents C10-C16alkenyl, R2 represents methyl and n is a numeral from 1
to 20;
b) At least one imidazoline compound (II),
Wherein one of R1 and R2 represents hydrogen and the other one represents a
substituent selected from the group consisting of CrCualkyl, hydroxy-C2-
C12alkyl,
amino-C2-C12alkyl and C12-C18alkenyl; or
Wherein both of R1 and R2 represent substituents selected from the group
consist-
ing of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl and C12-C18alkenyl;
and
c) At least one amine phosphate partial ester (III),
Wherein m represents 1 or 2;
n represents 2, if m represents 1, or represents 1, if m represents 2;
R represents a substituent selected from the group consisting of CrCualkyl, hy-

droxy-C2-C12alkyl and amino-C2-C12alkyl; and
Ra, Rb, Rc and Rd independently of one another represent hydrogen or a
substituent
selected from the group consisting of CrCualkyl and hydroxy-C2-C12alkyl; and
B) A functional fluid.
A particularly preferred embodiment of the invention relates to composition,
which comprises

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- 4 -
A) An additive mixture that essentially consists of
a) At least one alkenyl succinic half ester (I), wherein
R1 represents C12-C16alkenyl, R2 represents methyl and n is a numeral from 1
to
20;
b) At least one imidazoline compound (II),
Wherein one of R1 and R2 represents hydrogen and the other one represents a
substituent selected from the group consisting of C1-C12alkyl and C12-
C18alkenyl;
or
Wherein both of R1 and R2 represent substituents selected from the group con-
sisting of C1-C12alkyl and C12-C18alkenyl; and
c) At least one amine phosphate partial ester (III),
Wherein m represents 1 or 2;
n represents 2, if m represents 1, or represents 1, if m represents 2;
R represents a substituent selected from the group consisting of C1-C12alkyl
and
hydroxy-C2-C12alkyl; and
Ra, Rb, Rc and Rd independently of one another represent hydrogen or a
substitu-
ent selected from the group consisting of C1-C12alkyl and hydroxy-C2-C12alkyl;

and
B) A functional fluid.
A highly preferred embodiment of the invention relates to a composition, which
comprises
a) At least one alkenyl succinic half ester (I),
Wherein R1 represents C6-C18alkenyl, R2 represents methyl and n is a nu-
meral from 1 to 100;
b) At least one imidazoline compound (II),
Wherein one of R1 and R2 represents hydrogen and the other one repre-
sents a substituent selected from the group consisting of C1-C12alkyl, hy-
droxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl,
phenyl-C1atalkyl, Cratalkylphenyl and C1atalkylphenyl-Cratalkyl; or
Wherein both of R1 and R2 represent substituents selected from the group
consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl,

CA 02650246 2014-01-30
29276-1391
- 5 -
C2-C2oalkenyl, phenyl, phenyl- C1-C4alkyl, C1-C4alkylphenyl and
Cl-C4alkylphenyl-C1-C4alkyl;
c) At least one amine phosphate partial ester (III),
Wherein m represents 1 or 2;
n represents 2 if m represents 1; or
represents 1 if m represents 2; and
R represents a substituent selected from the group consisting of
C1-Ci2alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-
Cratalkyl, Ci-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl,
C4-C8cycloalkyl, C4-Cocycloalkyl-C1-C4alkyl, C1-C4alkyl-C4-Cocycloalkyl
and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl; and
R., Rb, Rd and Rd independently of one another represent hydrogen or a
substituent selected from the group consisting of C1-C12alkyl, hydroxy-
C2-Ci2alkyl, amino-C2-C12alkyl, phenyl, phenyl-Ci-C4alkyl,
C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl, C4-C8cycloalkyl,
C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-as-Cocycloalkyl and C1-C4alkyl-
C4-C8cycloalkyl-C1-C4alkyl; and
d) Additional customary additives.
A further aspect of the invention relates to an additive mixture that consists
of
a) at least one alkenyl succinic half ester (I),
CO-OH
CHT-00-0¨FCHT-C-04-H
n
R2 (I),

CA 02650246 2014-01-30
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- 5a -
wherein R1 represents C6-Ci8alkenyl, R2 represents hydrogen or methyl
and n is a numeral from 1 to 100;
b) at least one imidazoline compound (II),
NN¨R2
R1 (II),
wherein one of R1 and R2 represents hydrogen and the other one
represents a substituent selected from the group consisting of
hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C2oalkenyl,
phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and C1-C4alkylphenyl-
C1-C4alkyl; or
wherein both of R1 and R2 represent substituents selected from the
group consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl,
C2-C2oalkenyl, phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl and
C1-C4alkylphenyl-C1-C4alkyl; and
c) at least one amine phosphate partial ester (Ill),
¨Ra ¨
0
N
,P, RI( N
R,
(R0).; (0.). Rc
n (Ill),
wherein m represents 1 or 2;
n represents 2 if m represents 1; or
represents 1 if m represents 2; and

CA 02650246 2014-01-30
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- 5b -
R represents a substituent selected from the group consisting of
C1-Ci2alkyl, hydroxy-C2-C12alkyl, amino-C2-Ci2alkyl, C2-C20alkenyl,
phenyl, phenyl-C1-C4alkyl, C1-C4alkylphenyl, Ci-C4alkylphenyl-
C1-C4alkyl, C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-
C4-C8cycloalkyl and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl; and
Ra, Rb, Rc and Rd independently of one another represent hydrogen or a
substituent selected from the group consisting of C1-C12alkyl, hydroxy-
C2-Ci2alkyl, amino-C2-Ci2alkyl, C2-C2oalkenyl, phenyl, phenyl-
C1-C4alkyl, C1-C4alkylphenyl, C1-C4alkylphenyl-C1-C4alkyl,
C4-C8cycloalkyl, C4-C8cycloalkyl-C1-C4alkyl, C1-C4alkyl-C4-C8cycloalkyl
and C1-C4alkyl-C4-C8cycloalkyl-C1-C4alkyl.
The compositions as described above are suitable as corrosion inhibitor in
non-aqueous, partially aqueous or aqueous functional fluids or liquids.
The expressions and terms used above and below are preferably defined as
follows
in the description of the present invention:
In a compound (I) R1 defined Co-Ciaalkenyl is preferably straight chain or,
where
possible, branched radical, for example n-2-octenyl, n-2-dodecenyl, iso-
dodecenyl, or
is preferably a group of the partial formula
R CH=C¨C¨

H I
R,
Wherein R' and R" are independently of one another hydrogen or substantially
straight chain hydrocarbyl groups, with the proviso that the total number of
carbon
atoms in R is within the indicated ranges. Preferably R' and R" are C3-
C15alkyl or
C3-C15alkenyl groups. In a particu-

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- 6 -
lady advantageous embodiment, R has from about 16 to about 180-atoms, R' is
hydrogen or
Ci-C7alkyl or C2-C7alkenyl and R" is C5-Ci5alkyl or C5-Ci5alkenyl.
R2 is hydrogen or preferably methyl.
In a compound (I) the index n represents a numeral from 1 to about 100.
According to pre-
ferred embodiments n represents a numeral from 1 to about 20. Compounds (I)
are obtain-
able by reacting the R-substituted succinic acid with ethylene oxide or
ethylene glycol of de-
sired chain length, if R2 represents hydrogen, or with propylene oxide or
polypropylene glycol
of desired chain length, if R2 represents methyl.
Compounds (I) are known and at least some of them are commercially available.
The prepa-
ration of compounds (I) is described in British Patent Specification No.
795,491.
Compounds (I) are known oil soluble corrosion inhibitors, which are
commercially available
as solution in mineral oil, such as the product Ciba0 Irgacor0 L 12. Other
products are Hi-
tec0 536 commercially available from Ethyl Corp. Richmond VA, USA.
In a compound (II) one of R1 and R2 represents hydrogen and the other one
represents a
substituent selected from the group consisting of C1-C12alkyl, hydroxy-C2-
C12alkyl,
amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-C1atalkyl, Cratalkylphenyl
and
C1atalkylphenyl-Cratalkyl; or
Both of R1 and R2 represent substituents selected from the group consisting of
C1-C12alkyl,
hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl, phenyl-
C1atalkyl,
Cratalkylphenyl and C1atalkylphenyl-Cratalkyl.
R1 and R2 defined as C1-C12alkyl is, for example, C1-C6alkyl, e.g. methyl,
ethyl, n-propyl or
isopropyl or n-butyl, sec-butyl or tert-butyl or straight-chain or branched
pentyl or hexyl, and
C7-C12alkyl, e.g. straight-chain or branched heptyl, octyl, isooctyl, nonyl,
tert-nonyl, decyl, un-
decyl or dodecyl.
R1 and R2 defined as hydroxy-C2-C12alkyl, is e.g. 2-hydroxyethyl,
dihydroxyethyl, 2- or
3-hydroxypropyl, 2-, 3-dihydroxypropyl, glyceryl or any of the above-mentioned
at-Cualkyl
groups substituted by 1-3 hydroxy groups.
R1 and R2 defined as amino-C2-C12alkyl is e.g. 2-aminoethyl, diaminoethyl or 2-
or
3-aminopropyl or any of the above-mentioned at-Cualkyl groups substituted by 1-
3 amino
groups.
R1 and R2 defined as C2-C20alkenyl is a straight chain or, where possible,
branched radical,
for example vinyl, allyl, 2-butenyl, 3-butenyl, isobutenyl, n-2,4-pentadienyl,
3-methyl-2-bu-
tenyl, n-2-octenyl, n-2-dodecenyl or iso-dodecenyl.

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R1 and R2 defined as phenyl-C1atalkyl, Cratalkylphenyl and C1atalkylphenyl-
Cratalkyl
radicals are, for example, benzyl, 1- or 2-phenethyl, 4-methyl- or 4-
ethylphenyl, cumyl or
4-methylbenzyl.
According to preferred embodiments one of R1 and R2 represents hydrogen and
the other
one represents a substituent selected from the group consisting of CrCualkyl,
hy-
droxy-C2-C12alkyl, amino-C2-C12alkyl and C12-C18alkenyl; or
Both of R1 and R2 represent substituents selected from the group consisting of
CrCualkyl,
hydroxy-C2-C12alkyl, amino-C2-C12alkyl and C12-C18alkenyl.
According to another preferred embodiment one of R1 and R2 represents hydrogen
and the
other one represents a substituent selected from the group consisting of
CrCualkyl and
C12-Ci8alkenyl; or
Both of R1 and R2 represent substituents selected from the group consisting of
CrCualkyl
and C12-C18alkenyl.
Compounds (II) are known compounds and applicable oil soluble corrosion
inhibitors, which
are commercially available as solution in mineral oil, such as the product
Ciba Amine 0.
In a compound (III) m represents 1 or 2. In the event that m represents 1, n
represents 2.
Such compounds are represented by the formula
Ra
0 1 +
N
II
P, RI( I Rd
0
1 0 Rc d
RO -
0 _2
_
In the event that m represents 2, n represents 1. Such compounds are
represented by the
formula
RRa
0 1
I I N +
1:) I! 1
ROV 1 0- I Rd
Rc
OR
In a compound (III) R represents a substituent selected from the group
consisting of
CrCualkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, phenyl, phenyl-C1atalkyl,
Cratalkylphenyl, C1atalkylphenyl-Cratalkyl, a4-C8cycloalkyl, a4-C8cycloalkyl-
C1-a4alkyl,
C1-a4alkyl-C4-C8cycloalkyl and C1-a4alkyl-C4-C8cycloalkyl-C1-a4alkyl; and

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Ra, Rb, Rc and Rd independently of one another represent hydrogen or a
substituent selected
from the group consisting of CrCualkyl, hydroxy-C2-C12alkyl, amino-C2-
C12alkyl, phenyl,
phenyl-C1atalkyl, Cratalkylphenyl, C1atalkylphenyl-Cratalkyl, a4-C8cycloalkyl,

a4-C8cycloalkyl-C1-a4alkyl, C1-a4alkyl-C4-C8cycloalkyl and C1-a4alkyl-C4-
C8cyclo-
alkyl-C1atalkyl.
The definitions of CrCualkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, phenyl,
phenyl-C1atalkyl, Cratalkylphenyl, C1atalkylphenyl-Cratalkyl correspond to the
defini-
tions given above with regard to compounds (I) and (II).
R as well as Ra, Rb, Rc and Rd defined as a4-C8cycloalkyl, a4-C8cycloalkyl-C1-
a4alkyl,
C1-a4alkyl-C4-C8cycloalkyl and C1-a4alkyl-C4-C8cycloalkyl-C1-a4alkyl are, for
example,
cyclopentyl, cyclohexyl, cyclopentylmethyl or cyclohexylmethyl, cyclopenty1-
1,1-ethyl, cyclo-
hexy1-1,1-ethyl, cyclopenty1-1,2-ethyl, cyclohexy1-1,2-ethyl, cyclopenty1-1,2-
propyl or cyclohe-
xy1-1,2-propyl, which can be substituted on the a4-C8cycloalkyl groups by
Cratalkyl, e.g.
methyl, ethyl, n- propyl or isopropyl.
According to preferred embodiments R represents a substituent selected from
the group
consisting of CrCualkyl, hydroxy-C2-C12alkyl and amino-C2-C12alkyl; and
Ra, Rb, Rc and Rd independently of one another represent hydrogen or a
substituent selected
from the group consisting of CrCualkyl and hydroxy-C2-C12alkyl.
Amine phosphate partial ester as represented by the formula III are known
compounds that
can be prepared by known methods. Compounds (III) are applicable as oil
soluble corrosion
inhibitors and commercially available, such as the product Ciba Irgalube
349.
Other amine phosphate partial ester as represented by the formula III are
commercially
available from Rheinchemie Rheinau GmbH, Mannheim Germany, such as the
products Ad-
ditin RC 3740, RC 3741 or RC 3760 (amine neutralized phosphoric acid ester of
aliphatic
alcohols).
The term functional liquid includes non-aqueous, partially aqueous and aqueous
liquids
which are in contact with metals to be protected, in particular aluminium and
zinc.
Examples of non-aqueous functional liquids are fuels, e.g. hydrocarbon
mixtures comprising
mineral oil fractions which are liquid at room temperature and are suitable
for use in internal
combustion engines, e.g. internal combustion engines with external (petrol
engines) or inter-
nal ignition (diesel engines), e.g. petrol having different octane contents
(regular grade or
premium grade petrol) or diesel fuels, and lubricants, hydraulic fluids, metal
working fluids,

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such as drawing oil, cutting oils, forming oils, drilling oils etc, engine
coolants, transformer
oils and switchgear oils.
Examples of suitable partially aqueous functional liquids are water-in-oil or
oil-in-water metal
working fluids, hydraulic fluids based on aqueous polyglycol/ polyglycol ether
mixtures or gly-
col systems, and engine cooling systems based on aqueous glycol.
Examples of aqueous functional liquids are industrial cooling water, filling
compositions of a
water conditioning plant, steam generation systems, sea water evaporation
systems, sugar
evaporation systems, irrigation systems, hydrostatic boilers and heating
systems or cooling
systems having a closed circulation.
The composition according to the invention preferably comprise 0.01 to 10.0%
by weight, in
particular 0.02 to 3.0 % by weight, of the additive mixture, as defined above,
based on the
weight of the functional liquid.
Non-aqueous functional liquids are preferred, in particular base oils of
lubricating viscosity,
which can be used for the preparation of greases, metal working fluids, gear
fluids and hy-
draulic fluids.
Suitable greases, metal working fluids, gear fluids and hydraulic fluids are
based, for exam-
ple, on mineral or synthetic oils or mixtures thereof. The lubricants are
familiar to a person
skilled in the art and are described in the relevant literature, such as, for
example, in Chem-
istry and Technology of Lubricants; Mortier, R.M. and Orszulik, S. T.
(Editors); 1992 Blackie
and Son Ltd. for GB, VCH-Publishers N.Y. for U.S., ISBN 0-216-92921-0, cf.
pages 208 et
seq. and 269 et seq.; in Kirk-Othmer Encyclopedia of Chemical Technology,
Fourth Edition
1969, J. Wiley & Sons, New York, Vol. 13, page 533 et seq. (Hydraulic Fluids);
Performance
Testing of Hydraulic Fluids; R. Tourret and E.P. Wright, Hyden & Son Ltd. GB,
on behalf of
The Institute of Petroleum London, ISBN 0 85501 317 6; Ullmann's Encyclopedia
of Ind.
Chem., Fifth Completely Revised Edition, Verlag Chemie, DE-Weinheim, VCH-
Publishers for
U.S., Vol. A 15, page 423 et seq. (Lubricants), Vol. A 13, page 165 et seq.
(Hydraulic Fluids).
The lubricants are in particular oils and greases, for example based on
mineral oil, synthetic
oils, or vegetable and animal oils, fats, tallow and wax or mixtures thereof.
Vegetable and
animal oils, fats, tallow and wax are, for example, palm kernel oil, palm oil,
olive oil, colza oil,
rapeseed oil, linseed oil, soy bean oil, cotton wool oil, sunflower oil,
coconut oil, maize oil,
castor oil, walnut oil and mixtures thereof, fish oils, and chemically
modified, e.g. epoxidised
or sulphoxidised or alkylated or hydrogenated, forms or forms prepared by
genetic engi-
neering, for example soy bean oil prepared by genetic engineering.

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Examples of synthetic lubricants include lubricants based on aliphatic or
aromatic carboxylic
esters, polymeric esters, polyalkylene oxides, phosphoric acid esters, poly-a-
olefins or sili-
cones of the diester of a dibasic acid with a monohydric alcohol, e.g. dioctyl
sebacate or di-
nonyl adipate, of a triester of trimethylolpropane with a monobasic acid or
with a mixture of
such acids, e.g. trimethylolpropane tripelargonate, trimethylolpropane
tricaprylate or mixtures
thereof, of a tetra ester of pentaerythritol with a monobasic acid or with a
mixture of such ac-
ids, e.g. pentaerythrityl tetracaprylate, or of a complex ester of monobasic
and dibasic acids
with polyhydric alcohols, e.g. a complex ester of trimethylolpropane with
caprylic and sebacic
acid or of a mixture thereof. Particularly suitable in addition to mineral
oils are, for example,
poly-a-olefins, ester-based lubricants, phosphates, glycols, polyglycols and
polyalkylene gly-
cols and mixtures thereof with water.
Said lubricants or mixtures thereof can also be mixed with an organic or
inorganic thickener
(base fat). Metal working fluids and hydraulic fluids can be prepared on the
basis of the same
substances as described above for the lubricants. These are frequently also
emulsions of
such substances in water or other liquids.
Said lubricant compositions, e.g. greases, gear fluids, metal working fluids
and hydraulic flu-
ids, may additionally contain further additives which are added in order
further to improve
their fundamental properties. These include: antioxidants, metal deactivators,
rust inhibitors,
viscosity index improvers, pour point depressants, dispersants, detergents,
tackyfiers,
thixotropic builders, dewatering agents, antifoam agents, demulsifiers, high
pressure addi-
tives and antiwear additives. Such additives are added in the amounts
customary in each
case for the purpose, each in the range from 0.01 to 10.0% by weight. Examples
of further
additives follow:
1. Phenolic antioxidants
1.1. Alkylated monophenols: 2,6-di-tert-butyl-4-methylphenol, 2-butyl-4,6-
dimethylphenol,
2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-
tert-buty1-4-iso-
butylphenol, 2,6-dicyclopenty1-4-methylphenol, 2-(a-methylcyclohexyl)-4,6-
dimethyl-
phenol, 2,6-dioctadecy1-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-
buty1-4-
methoxymethylphenol, linear nonylphenols or nonylphenols which are branched in
the side chain, e.g. 2,6-dinony1-4-methylphenol, 2,4-dimethy1-6-(1'-methyl-
undec-l'-
y1)-phenol, 2,4-dimethy1-6-(1'-methylheptadec-l'-y1)-phenol, 2,4-dimethy1-6-
(1'-methyl-
tridec-1'-y1)-phenol and mixtures thereof

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1.2. Alkylthiomethylphenols: 2,4-dioctylthiomethy1-6-tert-butylphenol, 2,4-
dioctylthiomethy1-
6-methylphenol, 2,4-dioctylthiomethy1-6-ethylphenol, 2,6-didodecylthiomethy1-4-
nonyl-
phenol
1.3. Hydroduinones and alkylated hydroduinones: 2,6-di-tert-butyl-4-
methoxyphenol, 2,5-
di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-dipheny1-4-
octadecyl-
oxyphenol, 2,6-di-tert-butyl-hydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole,
3,5-di-
tert-buty1-4-hydroxyanisole, 3,5-di-tert-buty1-4-hydroxyphenylstearate,
bis(3,5-di-tert-
buty1-4-hydroxyphenyl) adipate
1.4. Tocopherols: ix-, p-, y- or 6-tocopherols and mixtures thereof
(vitamin E)
1.5. Hydroxylated thiodiphenyl ethers: 2,2'-thiobis(6-tert-butyl-4-
methylphenol),
2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-
thiobis-(6-
tert-buty1-2-methylphenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis(2,6-
dimethy1-
4-hydroxyphenyl) disulphide
1.6. Alkylidene bisphenols: 2,2'-methylenebis(6-tert-butyl-4-methylphenol),
2,2'-
methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methy1-6-(oc-
methylcy-
clohexyl)-phenol], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-
methylene-
bis(6-nony1-4-methylphenol), 2,2'-methylenebis(4,6-di-tert-butylphenol), 2,2'-
ethylidenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(6-tert-butyl-4-
isobutylphenol),
2,2'-methylenebis[6-(oc-methylbenzy1)-4-nonylphenol], 2,2'-methylenebis[6-
(oc,oc-di-
methylbenzy1)-4-nonylphenol], 4,4'-methylenebis(2,6-di-tert-butylphenol), 4,4'-
methyl-
enebis(6-tert-buty1-2-methylphenol), 1,1-bis(5-tert-buty1-4-hydroxy-2-methyl-
phenyl)butane, 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzy1)-4-methylphenol,
1,1,3-
tris(5-tert-buty1-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-buty1-4-
hydroxy-2-
methyl-pheny1)-3-n-dodecylmercaptobutane, ethylene glycol bis[3,3-bis(3'-tert-
butyl-
4'-hydroxyphenyl)butyrate], bis(3-tert-buty1-4-hydroxy-5-methyl-
phenyl)dicyclopenta-
diene, bis[2-(3'-tert-buty1-2'-hydroxy-5'-methyl-benzy1)-6-tert-butyl-4-methyl-
phenyl]
terephthalate, 1,1-bis(3,5-dimethy1-2-hydroxypheny1)-butane, 2,2-bis(3,5-di-
tert-buty1-
4-hydroxyphenyl)propane, 2,2-bis(5-tert-buty1-4-hydroxy-2-methylpheny1)-4-n-
dode-
cylmercaptobutane, 1,1,5,5-tetra(5-tert-buty1-4-hydroxy-2-methylphenyl)pentane
1.7. 0-, N- and S-benzyl compounds: 3,5,3',5'-tetra-tert-butyl-4,4'-
dihydroxydibenzyl ether,
octadecyl 4-hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecy1-4-hydroxy-3,5-
di-
tert-butylbenzylmercaptoacetate, tris(3,5-di-tert-buty1-4-hydroxybenzyl)amine,
bis(4-

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tert-buty1-3-hydroxy-2,6-dimethylbenzyl) dithioterephthalate, bis(3,5-di-tert-
buty1-4-hy-
droxybenzyl) sulphide, isooctyl 3,5-di-tert-buty1-4-
hydroxybenzylmercaptoacetate
1.8. Hydroxybenzylated malonates: dioctadecyl 2,2-bis(3,5-di-tert-buty1-2-
hydroxybenzy1)-
malonate, dioctadecyl 2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate,
didodecyl
mercaptoethy1-2,2-bis(3,5-di-tert-buty1-4-hydroxybenzyl)malonate, di44-
(1,1,3,3-
tetramethylbutyl)-phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate
1.9. Hydroxybenzyl aromatics: 1,3,5-tris(3,5-di-tert-buty1-4-
hydroxybenzy1)-2,4,6-trimethyl-
benzene, 1,4-bis(3,5-di-tert-buty1-4-hydroxybenzy1)-2,3,5,6-
tetramethylbenzene,
2,4,6-tris(3,5-di-tert-buty1-4-hydroxybenzyl)phenol
1.10. Triazine compounds: 2,4-bisoctylmercapto-6-(3,5-di-tert-buty1-4-
hydroxyanilino)-1,3,5-
triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-buty1-4-hydroxyanilino)-1,3,5-
triazine, 2-
octylmercapto-4,6-bis(3,5-di-tert-buty1-4-hydroxyphenoxy)-1,3,5-triazine,
2,4,6-
tris(3,5-di-tert-buty1-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-tris(3,5-di-
tert-buty1-4-hy-
droxybenzyl) isocyanurate, 1,3,5-tris(4-tert-buty1-3-hydroxy-2,6-
dimethylbenzyl) iso-
cyanurate, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine,
1,3,5-
tris(3,5-di-tert-buty1-4-hydroxyphenylpropiony1)-hexahydro-1,3,5-triazine,
1,3,5-
tris(3,5-dicyclohexy1-4-hydroxybenzyl) isocyanurate
1.11. Acylaminophenols: 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N-
(3,5-di-tert-
buty1-4-hydroxyphenyl) carbamate
1.12. Esters of beta-(3,5-di-tert-butyl-4-hydroxypheny1)-propionic acid with
monohydric or
polyhydric alcohols, e.g. with methanol, ethanol, n-octanol, isooctanol,
octadecanol,
1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol,
neopentylglycol,
thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol,

tris(hydroxyethyl) isocyanurate, N,N'-bis(hydroxyethyl)oxalamide, 3-
thiaundecanol,
3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethy1-1-

phospha-2,6,7-trioxabicyclo[2.2.2]octane
1.13. Esters of beta-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid
(with monohydric
or polyhydric alcohols), e.g. the alcohols with methanol, ethanol, n-octanol,
isooc-
tanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-
propanediol,
neopentylglycol, thiodiethylene glycol, diethylene glycol, triethylene glycol,
pentae-
rythritol, tris(hydroxyethyl) isocyanurate, N,N'-bis(hydroxyethyl)-oxalamide,
3-
thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-
hy-
droxymethy1-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane

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1.14. Esters of beta-(3,5-dicyclohexy1-4-hydroxyphenyl)propionic acid with
monohydric or
polyhydric alcohols, e.g. the alcohols stated under 13.
1.15. Ester of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid with monohydric or
polyhydric
alcohols, e.g. the alcohols stated under 13.
1.16. Amides of beta-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, e.g.
N,N'-bis(3,5-di-
tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamine, N,N'-bis(3,5-di-tert-
butyl-
4-hydroxyphenylpropionyl)trimethylenediamine, N,N'-bis(3,5-di-tert-butyl-4-
hydroxy-
phenylpropionyl)hydrazine
1.17. Ascorbic acid (vitamin C)
1.18. Amine antioxidants: N,N'-diisopropyl-p-phenylenediamine, N,N'-di-sec-
butyl-p-
phenylenediamine, N,N'-bis(1,4-dimethylpentyI)-p-phenylenediamine, N,N'-bis(1-
ethyl-3-methylpenty1)-p-phenylenediamine, N,N'-bis(1-methyl-heptyI)-p-
phenylenediamine, N,N'-dicyclohexyl-p-phenylenediamine, N,N'-diphenyl-p-
phenylenediamine, N,N'-di-(naphth-2-yI)-p-phenylenediamine, N-isopropyl-N'-
phenyl-
p-phenylenediamine, N-(1,3-dimethyl-butyl)-N'-phenyl-p-phenylenediamine, N-(1-
methylheptyI)-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-
phenylenediamine, 4-(p-toluenesulphonamido)diphenylamine, N,N'-dimethyl-N,N'-
di-
sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-
isopropoxy-
diphenylamine, N-phenyl-1-naphthylamine, N-(4-tert-octylphenyI)-1-
naphthylamine,
N-phenyl-2-naphthylamine, octylated diphenylamine, e.g. p,p'-di-tert-
octyldiphenyl-
amine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylamino-phenol, 4-
do-
decanoylaminophenol, 4-octadecanoylaminophenol, di-(4-methoxyphenyl)amine, 2,6-

di-tert-butyl-4-dimethylaminomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-
diami-
nodiphenylmethane, N,N,N',N'-tetramethy1-4,4'-diaminodiphenylmethane, 1,2-di-
[(2-
methyl-phenyl)amino]ethane, 1,2-di-(phenylamino)-propane, (o-tolyl)biguanide,
di44-
(1,3'-dimethyl-butyl)phenyl]amine, tert-octylated N-phenyl-1-naphthylamine,
mixture
of mono- and dialkylated tert-butyl/tert-octyldiphenylamines, mixture of mono-
and
dialkylated nonyldiphenylamines, mixture of mono- and dialkylated
dodecyldiphenyl-
amines, mixture of mono- and dialkylated isopropyl/isohexyldiphenylamines,
mixtures
of mono- and dialkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethy1-4H-
1,4-
benzothiazine, phenothiazine, mixture of mono- and dialkylated tert-butyl tert-
octyl-
phenothiazines, mixture of mono- and dialkylated tert-octylphenothiazines, N-
allyl-
phenothiazine, N,N,N',N'-tetrapheny1-1,4-diaminobut-2-ene, N,N-bis-(2,2,6,6-
tetrame-

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thylpiperidin-4-y1)-hexamethylenediamine, bis-(2,2,6,6-tetramethylpiperidin-4-
y1) seba-
cate, 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethylpiperidin-4-ol
2. Further antioxidants: aliphatic or aromatic phosphites, esters of
thiodipropionic acid or
thiodiacetic acid or salts of dithiocarbamic or dithiophosphoric acid,
2,2,12,12-tetra-
methyl-5,9-dihydroxy-3,7,11-trithiatridecane and 2,2,15,15-tetramethy1-5,12-
dihy-
droxy-3,7,10,14-tetrathiahexadecane
3. Further metal deactivators:
3.1. Benzotriazoles and derivatives thereof: 2-mercaptobenzotriazole, 2,5-
dimercaptoben-
zotriazole, 4- or 5-alkylbenzotriazoles (e.g. tolutriazole) and derivatives
thereof,
4,5,6,7-tetrahydrobenzotriazole, 5,5'-methylenebisbenzotriazole; Mannich bases
of
benzotriazole or tolutriazole, such as 14di(2-
ethylhexylaminomethyl)]tolutriazole and
14di(2-ethylhexylaminomethyl)]benzotriazole; alkoxyalkylbenzotriazoles, such
as 1-
(nonyloxymethyl)-benzotriazole, 1-(1-butoxyethyl)benzotriazole and 1-(1-
cyclohexyl-
oxybutyl)tolutriazole
3.2. 1,2,4-Triazoles and derivatives thereof: 3-alkyl (or aryl)-1,2,4-
triazoles, Mannich
bases of 1,2,4-triazoles, such as 1-[di(2-ethylhexyl)aminomethyl]-1,2,4-
triazole;
alkoxyalky1-1,2,4-triazoles, such as 1-(1-butoxyethyl)-1,2,4-triazole;
acylated 3-amino-
1,2,4-triazoles
3.3. Imidazole derivatives: 4,4'-methylenebis(2-undecy1-5-methylimidazole),
bis[(N-
methypimidazol-2-yl]carbinol octyl ether
3.4. Sulphur-containing heterocyclic compounds: 2-mercaptobenzothiazole,
2,5-dimer-
capto-1,3,4-thiadiazole, 2,5-dimercaptobenzothiadiazole and derivatives
thereof; 3,5-
bis[di-(2-ethylhexyl)aminomethyI]-1,3,4-thiadiazolin-2-one
3.5. Amino compounds: salicylidenepropylenediamine, salicylaminoguanidine
and salts
thereof
4. Corrosion inhibitors:

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4.1. Organic acids, their esters, metal salts, amine salts and
anhydrides: alkyl- and al-
kyenylsuccinic acids and partial esters thereof with alcohols, diols or
hydroxycarbox-
ylic acids, partial amides of alkyl- and alkenylsuccinic acids, 4-
nonylphenoxyacetic
acid, alkoxy- and alkoxyethoxycarboxylic acids, such as dodecyloxyacetic acid,
dode-
cyloxy(ethoxy)acetic acid and amine salts thereof, and furthermore N-
oleoylsarcosine,
sorbitan monooleate, lead naphthenate, alkenylsuccinic anhydrides, e.g.
dodecenyl-
succinic anhydride, 2-(2-carboxyethyl)-1-dodecy1-3-methylglycerol and salts
thereof,
in particular sodium salts and triethanolamine salts
4.2. Nitrogen-containing compounds:
4.2.1 Tertiary aliphatic and cycloaliphatic amines and amine salts of organic
and inorganic
acids, e.g. oil-soluble alkylammonium carboxylates, and furthermore 1-[N,N-bis-
(2-hy-
droxyethyl)amino]-3-(4-nonylphenoxy)propan-2-ol
4.2.2 Heterocyclic compounds, e.g. substituted imidazolines and oxazolines,
e.g. 2-hepta-
deceny1-1-(2-hydroxyethyl)-imidazoline
5. Sulphur-containing compounds: barium dinonylnaphthalenesulphonates,
calcium
petroleum sulphonates, alkylthio-substituted aliphatic carboxylic acids,
esters of ali-
phatic 2-sulphocarboxylic acids and salts thereof
6. Viscosity index improvers: polyacrylates, polymethacrylates,
vinylpyrroli-
done/methacrylate copolymers, polyvinylpyrrolidiones, polybutenes, olefin
copoly-
mers, styrene/acrylate copolymers, polyethers
T Pour point depressants: poly(meth)acrylates, ethylene-vinyl acetate
copolymers, alkyl
polystyrenes, fumarate copolymers, alkylated naphthalene derivatives
8. Dispersants/Surfactants: polybutenylsuccinamides or
polybutenylsuccinimides,
polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium
sul-
phonates and phenolates
9. High pressure and antiwear additives: sulphur- and halogen-containing
compounds,
e.g. chlorinated paraffins, sulphonated olefins or vegetable oils (soy bean
oil, rape-
seed oil), alkyl or aryl di- or trisulphides, benzotriazoles or derivatives
thereof, such as

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- 16 -
bis (2-ethylhexyl)aminomethyl tolutriazoles, dithiocarbamates, such as
methylenebis-
dibutyl dithiocarbamate, derivatives of 2-mercaptobenzothiazole, such as 14N,N-

bis(2-ethylhexyl)aminomethyl]-2-mercapto-1H-1,3-benzothiazole, derivatives of
2,5-
dimercapto-1,3,4-thiadiazole, such as 2,5-bis(tert.nonyldithio)-1,3,4-
thiadiazole
10. Substances for reducing the coefficient of friction: lard oil, oleic
acid, tallow, rapeseed
oil, sulphurised fats, amines. Further examples are stated in EP-A-0 565 487
11. Special additives for use in water/oil metal processing and
hydraulic fluids:
11.1 Emulsifiers: petroleum sulphonates, amines, such as polyoxyethylated
fatty amines,
non-ionic surface-active substances
11.2 Buffers: alkanolamines
11.3 Biocides: triazines, thiazolinones, trisnitromethane, morpholine,
sodium pyridinethiol
11.4 Processing speed improvers: calcium sulphonates and barium sulphonates
11.5 Tackifiers: acrylamide copolymer, polyisubutene resins.
11.6 Thixotropic builders: microcrystalline waxes, oxidized waxes and oxidized
esters
11.7 Dewatering agents: polyglycol ethers, butyldiglycols.
Said components can be mixed with the lubricants in a manner known per se. It
is also possi-
ble to prepare a concentrate or a so-called additive package, which can be
diluted to the con-
centrations of use for the corresponding lubricant according to the
application purposes as
intended.
The ratio of component a) to component b) to component b) present in the
additive mix-
ture A) may vary within the ranges of approximately from 10 : 10 : 80 and 80 :
10 : 10 to 10 :
80: 10% by weight.
Although the total content of the additive mixture A) in the composition is
not critical, the
preferred total content of the additive mixture A) in the composition is in
the range between
10.0 and 0.01, preferably 10.0 and 0.1 or 3.0 and 0.1% by weight, based on the
total weight
of the composition.

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A further embodiment of the invention relates to an additive mixture that
essentially consists
of
a) At least one alkenyl succinic half ester (I),
Wherein R1 represents C6-C18alkenyl, R2 represents hydrogen or methyl
and n is a numeral from 0 to 100;
b) At least one imidazoline compound (II),
Wherein one of R1 and R2 represents hydrogen and the other one repre-
sents a substituent selected from the group consisting of C1-C12alkyl, hy-
droxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl,
phenyl-C1atalkyl, Cratalkylphenyl and C1atalkylphenyl-Cratalkyl; or
Wherein both of R1 and R2 represent substituents selected from the group
consisting of C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl,
C2-C20alkenyl, phenyl, phenyl-C1atalkyl, Cratalkylphenyl and
C1atalkylphenyl-Cratalkyl; and
c) At least one amine phosphate partial ester (III),
Wherein m represents 1 or 2, n represents 2, if m represents 1; or repre-
sents 1, if m represents 2;
R represents a substituent selected from the group consisting of
C1-C12alkyl, hydroxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl,
phenyl-C1atalkyl, Cratalkylphenyl, C1atalkylphenyl-Cratalkyl,
a4-C8cycloalkyl, a4-C8cycloalkyl-C1-a4alkyl, C1-a4alkyl-C4-C8cycloalkyl and
C1-a4alkyl-C4-C8cycloalkyl-C1-a4alkyl; and
Ra, Rb, Rc and Rd independently of one another represent hydrogen or a
substituent selected from the group consisting of C1-C12alkyl, hy-
droxy-C2-C12alkyl, amino-C2-C12alkyl, C2-C20alkenyl, phenyl,
phenyl-C1atalkyl, Cratalkylphenyl, C1atalkylphenyl-Cratalkyl,
a4-C8cycloalkyl, a4-C8cycloalkyl-C1-a4alkyl, C1-a4alkyl-C4-C8cycloalkyl and
C1-a4alkyl-C4-C8cycloalkyl-C1-a4alkyl.
The definitions of components a), b) and c) present in the additive mixture
corresponds to the
definitions of components a), b) and c) present in the compositions as defined
above.
According to a preferred embodiment, the invention relates to the additive
mixture, as de-
fined above, used as additives in a metal working fluid.

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- 18 -
The invention also relates to the process for protection against corrosion or
oxidative degra-
dation of metals, wherein the metal is exposed to a functional fluid
comprising the additive
mixture as defined above.
According to a preferred embodiment, the invention relates to the process for
protection
against corrosion or oxidative degradation of zinc, aluminum or alloys
thereof, wherein zinc,
aluminum or alloys thereof are exposed to a functional fluid comprising the
additive mixture
as defined above.
A further embodiment of the invention relates to a process for protection
against corrosion or
oxidative degradation of zinc, aluminum or alloys thereof, wherein zinc,
aluminum or alloys
thereof are exposed to a functional fluid comprising at least one alkenyl
succinic half ester of
the formula I as defined above, wherein R1 represents C6-C18alkenyl, R2
represents hydrogen
or methyl and n is a numeral from 1 to 100.
The following Examples illustrate the invention:
Application Examples
A typical test procedure to test the corrosion inhibition is the climate
chamber test according
to DIN EN ISO 6270-2. This test is slightly modified by using several
different metal samples
and more severe conditions. Each sample is treated in the following test
cycle:
Exposure for 8 hours in a closed climate chamber at 50 3 C, humidity ca.
100%, followed
by 16 hours in an open climate chamber, cooling at 21 3 C and humidity
approaching am-
bient. The test cycles are repeated until 100% corrosion is detected visually.
In the event that
the test sample is not corroded, the test procedure is stopped after 24
cycles.

CA 02650246 2014-01-30
, 29276-1391
- 19 -
7C:OtitiMititittitORMItiott$peafflowalmasooduotovoet Additive treat
Reference oil Zinc 19
app. 15-20%
Mixture A Zinc >24
3%
Mixture B Zinc >24
5%
Mixture C Zinc > 24
3%
Mixture D Zinc 20
3%
Reference oil Aluminum 0
app. 15-20%
Mixture A Aluminum >15
3%
Mixture B Aluminum >15
5%
Mixture C Aluminum > 15
3%
Mixture D Aluminum > 15
3%
Reference oil: VDA 230- 201:
Mixture A = 3% lrgacor 112 in a paraffinic base oil
Mixture B = 5% Irgalubet 349 In a parafinic base oil
Mixture C = 0.9% IRGACOR L12; 1.5% Amine 0; 0.6% IRGALUBE 349 in an naphthenic

base oil
Mixture D = 0.6% IRGACOR L12; 0.9% Amine 0; 1.5% IRGALUBE 349 in a paraffinic
base
oil.

Representative Drawing

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Administrative Status

For a clearer understanding of the status of the application/patent presented on this page, the site Disclaimer , as well as the definitions for Patent , Administrative Status , Maintenance Fee  and Payment History  should be consulted.

Administrative Status

Title Date
Forecasted Issue Date 2014-12-23
(86) PCT Filing Date 2007-05-15
(87) PCT Publication Date 2007-11-29
(85) National Entry 2008-10-23
Examination Requested 2012-05-14
(45) Issued 2014-12-23
Deemed Expired 2017-05-15

Abandonment History

There is no abandonment history.

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Registration of a document - section 124 $100.00 2008-10-23
Application Fee $400.00 2008-10-23
Registration of a document - section 124 $100.00 2009-02-13
Maintenance Fee - Application - New Act 2 2009-05-15 $100.00 2009-03-18
Maintenance Fee - Application - New Act 3 2010-05-17 $100.00 2010-04-26
Maintenance Fee - Application - New Act 4 2011-05-16 $100.00 2011-04-21
Maintenance Fee - Application - New Act 5 2012-05-15 $200.00 2012-04-19
Request for Examination $800.00 2012-05-14
Maintenance Fee - Application - New Act 6 2013-05-15 $200.00 2013-04-23
Maintenance Fee - Application - New Act 7 2014-05-15 $200.00 2014-04-25
Final Fee $300.00 2014-09-22
Maintenance Fee - Patent - New Act 8 2015-05-15 $200.00 2015-04-20
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
CIBA HOLDING INC.
Past Owners on Record
CIBA SPECIALTY CHEMICALS HOLDING INC.
HABEREDER, TASSILO
KELLER, ANJA
MICHEL, KARL-HEINZ
NEHLS, ERIC
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Abstract 2008-10-23 1 56
Claims 2008-10-23 5 176
Description 2008-10-23 19 830
Cover Page 2009-02-19 1 29
Cover Page 2014-12-03 1 28
Description 2014-01-30 21 885
Claims 2014-01-30 7 200
PCT 2010-07-20 1 50
PCT 2008-10-23 4 151
Assignment 2008-10-23 5 144
Correspondence 2009-02-17 1 27
Assignment 2009-02-13 2 79
Assignment 2009-03-31 1 47
PCT 2010-06-22 1 43
Prosecution-Amendment 2012-05-14 2 76
Prosecution-Amendment 2013-07-30 3 108
Prosecution-Amendment 2014-01-30 15 488
Correspondence 2014-09-22 2 78