CA2234844C - Use of quaternized imidazoles as corrosion inhibitors for non-ferrous metals, and coolant compositions and antifreeze concentrates comprising them - Google Patents

Use of quaternized imidazoles as corrosion inhibitors for non-ferrous metals, and coolant compositions and antifreeze concentrates comprising them Download PDF

Info

Publication number
CA2234844C
CA2234844C CA002234844A CA2234844A CA2234844C CA 2234844 C CA2234844 C CA 2234844C CA 002234844 A CA002234844 A CA 002234844A CA 2234844 A CA2234844 A CA 2234844A CA 2234844 C CA2234844 C CA 2234844C
Authority
CA
Canada
Prior art keywords
concentrate
alkyl
weight
quaternized
total amount
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA002234844A
Other languages
French (fr)
Other versions
CA2234844A1 (en
Inventor
Ladislaus Meszaros
Michael Gillich
Klaus Pfitzner
Knut Oppenlander
Wolfgang Gunther
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE19605509A external-priority patent/DE19605509A1/en
Application filed by BASF SE filed Critical BASF SE
Publication of CA2234844A1 publication Critical patent/CA2234844A1/en
Application granted granted Critical
Publication of CA2234844C publication Critical patent/CA2234844C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Landscapes

  • Preventing Corrosion Or Incrustation Of Metals (AREA)

Abstract

Quaternized imidazoles I (see formula I) in which R1 and R3 independently of one another are saturated or unsaturated hydrocarbon radicals of 1-12 carbon atoms which can be substituted by oxygen-functional groups or interrupted by nonadjacent oxygens, R2, R4 and R5 independently of one another are hydrogen or saturated or unsaturated hydrocarbon radicals of 1-12 carbon atoms which can be substituted by oxygen-functional groups or interrupted by nonadjacent oxygens, it being possible for R4 and R5, together with the corresponding imidazole carbons, to form a five- or six-membered ring, and X.THETA. is an anion, are used as corrosion inhibitors in the corrosion protection of nonferrous metals, especially for car radiator protection.

Description

Use of quaternized imidazoles as corrosion inhibitors for non-ferrous metals, and coolant compositions and antifreeze concen-trates comprising them The present invention relates to the use of specific quaternized imidazoles as corrosion inhibitors for preventing the corrosion of nonferrous metals. The invention also relates to antifreeze concentrates and to ready-to-use aqueous coolant compositions comprising these quaternized imidazoles, and to a method of treating aqueous liquids with these quaternized imidazoles in order to reduce the corrosion of nonferrous metals.
Antifreeze for the cooling circuits of internal-combustion engines, as in automobiles, generally contains an alkylene gly-col, especially ethylene glycol or propylene glycol, as the principal component. For use in the cooling system these are diluted with water and are intended to provide not only for protection from frost but also for good heat dissipation. Alkyl-ene glycol/water mixtures, however, are highly corrosive at the operating temperatures of internal-combustion engines, and there-fore the various metals and their alloys present in the cooling system must be provided with sufficient protection against a wide variety of types of corrosion, such as pitting, crevice corro-sion, erosion or cavitation. For use as corrosion inhibitors in such cooling systems the prior art already includes a multi-plicity of individual chemicals.
As far as temperature stress on the heat transfer faces, pres-sure, flow rate and the selection of appropriate materials are concerned, the operating conditions in modern internal-combustion engines nowadays place very much greater demands on the anticor-rosion capacity of the coolant than was previously the case. In addition to the known materials, such as copper, brass, soft sol-der, steel and gray cast iron, aluminum alloys are being used to an increasing extent. Consequently, more of the recent patent literature describes specific combinations of long-known active substances, each claimed to have its own specific spectrum of ac-tion.
For instance, EP-B 229 440 (1) describes the combination of the salt of an aliphatic monobasic C3-Cls acid, the salt of a dibasic Cs-his-hydrocarbon acid and a hydrocarbon-triazole as an effective inhibitor formulation in a liquid-alcoholic freezing-point reducer for protecting aluminum alloys against pitting. It is additionally possible to employ other customary inhibitors, such _ 2 as alkali metal borate, silicate, benzoate, nitrate, nitrite or molybdate, and/or a hydrocarbazole.
EP A 564 721 (2) discloses antifreeze compositions, in particular for car radiator protection, which comprise a combination of the salt of an aliphatic monobasic C5-C1s acid, a hydrocarbon-triazole and imidazole as effective inhibitor formulation in a liquid-alcoholic freezing-point reducer. The imidazole concerned includes unsubstituted imidazole and also alkyl- and aryl-substituted imidazole.
A deficiency of the known inhibitor combinations is that, as far as nonferrous metal protection is concerned, they lose marks at elevated temperatures. For example, the hydrocarbon-triazoles which are employed predominantly in this context, for example benzotriazole and toluotriazole, lose their effectiveness above about 130°C.
It is an object of the present invention, therefore, to find sub-stances which raise the high-temperature protection afforded to nonferrous metals by customary inhibitor systems without a drop in protection for the other metals, especially aluminum alloys.
we have found that this object is achieved by the extensive replacement, in customary inhibitor systems, of the hydrocarbon-triazoles, such as benzotriazole or toluotriazole, by quaternized imidazoles, resulting in a marked improvement in the protection afforded to nonferrous metals, especially copper, brass and bronze, under high temperature stress.
It has been found that quaternized imidazoles of the general formula I

X~ (I) I

where R1 and R3 independently of one another are saturated or unsatu-rated hydrocarbon radicals of 1-12 carbon atoms which can be substituted by oxygen-functional groups or interrupted by nonadjacent oxygens, R2, R4 and R5independently of one another are hydrogen or satura-ted or unsaturated hydrocarbon radicals of 1-12 carbon atoms which can be substituted by oxygen-functional groups or interrupted by nonadjacent oxygens, it being possible for R4 and R5, together with the corresponding imidazole carbons, to form a five- or six~nembered ring, and Xe is an anion, are generally suitable as corrosion inhibitors in connection with the corrosion protection of nonferrous metals, especially copper, brass and bronze.
15 Particularly suitable oxygen-functional groups for R1 to RS are hydroxyl, carbonyl, carboxyl and C1-C4-alkoxycarbonyl. Depending on the size of R1 to R5 it is possible for each to carry 1-6, in particular 1-3, of such groups. Similarly, 1-6, especially 1-3, ether oxygens can be present per radical.
Preference is given in this context to quaternized imidazoles I
where R1 is C1-C4-alkyl, Ca-C4-a.lkenyl, C2-C4-hydroxyalkyl, 25 phenyl-C1-C4-alkyl, phenyl or tolyl, RZ is hydrogen or C1-C4-alkyl, R3 is C1-C4-alkyl or benzyl, R4 and RS are hydrogen, C1-C4-alkyl or together are a benzo-fused ring, and Xe is a mono-C1-C4-alkyl sulfate anion, half the stoichiometric amount of sulfate or of hydrogen phosphate (HP04ae), dihydrogen phosphate (H2P04e), a third of the stoichiometric amount of phosphate .. zR. ...~., ,. ; .a.. ~., i.,-r"n; ao ( PU4''" ) , o= nitr a to , c.:li.ivr i.uc yr ui v.a.~...... .
Particularly preferred quaternized imidazoles I are 1-methyl-imidazole, 1-ethylimidazole, 1-(~-hydroxyethyl)imidazole, 1,2-di-methylimidazole, 1-phenylimidazole, benzimidazole and, in par-ticular, N vinylimidazole, which are quaternized with benzyl chloride, benzyl bromide, methyl chloride, methyl bromide, ethyl chloride, ethyl bromide, diethyl sulfate or, in particular, dimethyl sulfate.

The anions mentioned, where not obtained via the quaternizing agent, can also be obtained by customary anion exchange methods on the quaternized system. In the case of quaternization with dialkyl sulfates it is possible for one or two alkyl groups to be transferred, resulting in the anions R30S03e or S04ze (in half the stoichiometric amount).
For the present invention, very special interest attaches to N vinylimidazole quaternized with dimethyl sulfate.
The present invention additionally relates to antifreeze con-centrates based on alkylene glycols or derivatives thereof and comprising 0.0005-2$ by weight, preferably 0.01-1~ by weight, especially 0.05-0.5$ by weight, based on the overall amount of concentrate, of one or more of the abovementioned quaternized imidazoles I.
The hydrocarbon-triazoles of unfavorable temperature stability, such as benzotriazole or toluotriazole, which are commonly present in such antifreeze compositions, can~be largely or com-pletely replaced by the quaternized imidazoles I described. Since under certain circumstances, however, advantages are possible in respect of the protective action for nonferrous metals, owing to synergistic effects between small amounts of hydrocarbon-triazoles and quaternized imidazoles I, a preferred embodiment of the present invention relates to novel antifreeze concentrates which additionally comprise up to 0.3$ by weight, in particular 0.001-0.1~ by weight, especially 0.005-0.05 by weight, based on the total amount of concentrate, of at least one hydrocarbon-triazole and/or hydrocarbon-thiazole.
Since in some cases it is also possible to find synergistic effects between the quaternized imidazoles I and nonquaternized imidazoles as described in (2), a further preferred embodiment of the present invention relates to novel antifreeze concentrates which additionally comprise 0.001-5~ by weight, in particular 0.01-2~ by weight, especially 0.05-1~ by weight, based on the total amount of concentrate, of nonquaternized imidazole and/or at least one nonquaternized alkyl- or aryl-substituted imidazole, for example a 1-(C1-C4-alkyl)imidazole or 1-phenylimidazole.
In addition, the novel antifreeze concentrates may also comprise all other customary inhibitor components for antifreeze formula-tions, including in particular:

- up to 5~ by weight, especially 0.05-3$ by weight, based on the total amount of concentrate, of alkali metal borates, eg.
sodium tetraborate (borax), and/or alkali metal phosphates, eg. disodium hydrogen phosphate or trisodium phosphate;

- up to 5~ by weight, especially 0.05-4$ by weight, based on the total amount of concentrate, of at least one aliphatic or aromatic dicarboxylic acid of 4-16 carbon atoms, in par-ticular 8-12 carbon atoms, in the form of its alkali metal salts, ammonium salts or amine salts, eg. the disodium salts or dipotassium salts of suberic, azelaic, sebacic, undecane-dioic, dodecanedioic, dicyclopentadienedicarboxylic, phthalic or terephthalic acid;
- up to 5$ by weight, especially 0.05-4~ by weight, based on the total amount of concentrate, of at least one aliphatic or aromatic monocarboxylic acid of 3-16 carbon atoms, in par-ticular 5-12 carbon atoms, 7 carbons being the minimum for aromatic monocarboxylic acids, in the form of its alkali metal salts, ammonium salts or amine salts, eg. the sodium salts or potassium salts of pentanoic, hexanoic, octanoic, 2-ethylhexanoic, nonanoic, decanoic, undecanoic, dodecanoic, benzoic or methylbenzoic acid;
- one or more corrosion inhibitors from the group consisting of alkali metal silicates, molybdates, nitrites and nitrates, and magnesium nitrate, each in amounts of up to 1~ by weight, especially 0.05-0.8~ by weight, based on the total amount of concentrate; examples are sodium metasilicate, sodium nitrite, sodium nitrate and sodium molybdate.
When alkali metal silicates are also used, they are advantageous-ly stabilized using customary organosilicophosphonates or organo-silicosulfonates in customary amounts.
In addition to the abovementioned inhibitor components it a.s also possible, for example, to employ hydrocarbazoles in customary amounts.
The overall corrosion inhibitor component can be up to 15~ by weight, in particular up to 10~ by weight, of the total amount of concentrate, where the concentration of individual constituents can be up to 5~ by weight.
The novel antifreeze concentrates can additionally comprise up to 1~ by weight, in particular 0.01-0.5~ by weight, based on the total amount of concentrate, of hard-water stabilizers based on polyacrylic acid, polymaleic acid, acrylic acid-malefic acid copolymers, polyvinylpyrrolidone, polyvinylimidazole, vinyl-pyrrolidone-vinylimidazole copolymers and/or copolymers of unsaturated carboxylic acids and olefins.
The pH of the novel antifreeze concentrates is commonly 6-11, preferably 7-9, in particular 7.1-7.3, and is generally estab-lished at the desired level by adding alkali metal hydroxide, ammonia or amines to the formulation; solid sodium hydroxide and potassium hydroxide, and aqueous solutions thereof, are particu-larly suitable for this purpose. Any aliphatic or aromatic mono-and/or dicarboxylic acids used are advantageously added directly as the corresponding alkali metal salts so as to establish the desired pH range automatically, but these carboxylic acids can also be added as the free acids, after which the formulation is neutralized with alkali metal hydroxide, ammonia or amines and the desired pH range is established.
Suitable liquid-alcoholic freezing-point reducers, which normally make up the major constituent (generally at least 80$ by weight, in particular at least 90~ by weight) of the novel antifreeze concentrates, are alkylene glycols or derivatives thereof, espe-cially propylene glycol and, in particular, ethylene glycol. How-ever, higher glycols and glycol ethers are also suitable, exam-ples being diethylene glycol, dipropylene glycol and monoethers of glycols, such as the methyl, ethyl, propyl and butyl ethers of ethylene, propylene, diethylene and dipropylene glycols. It is also possible to use mixtures of said glycols and glycol ethers.
The present invention also relates to ready-to-use aqueous coolant compositions of reduced freezing point, especially for car radiator protection, which comprise water and 10-90~ by weight, preferably 20-60~ by weight, of the novel antifreeze concentrates.
The present invention relates, moreover, to a method of treating aqueous liquids comprising a water-soluble freezing-point reducer based on alkylene glycols or derivatives thereof in order to reduce the corrosion of nonferrous metals in contact with the aqueous liquids, which comprises admixing to the aqueous liquids an effective amount of one or more quaternized imidazoles I. For the corrosion-inhibiting imidazoles I, this amount is normally 0.0005-2~ by weight, preferably 0.01-1$ by weight, especially 0.05-0.5~ by weight, based on the total amount of freezing-point reducer and all associated corrosion inhibitors and other additives.

Examples The present invention is illustrated using Examples A, B, D and G
of the invention and Comparison Examples C, E, F and X. Table 1 shows the composition of the inhibitor mixtures, in ethylene glycol, which are used to illustrate the invention. These anti-freeze concentrates were diluted with water and subjected to standard corrosion tests.
The results obtained in the ASTM D 1384 corrosion test (Table 2) first of all show clearly that the quaternary structure of the imidazoles constitutes the principle of action of the novel non-ferrous metal protector. Thus Examples C and D illustrate, in direct comparison between l~nethylimidazole and the same compound quaternized with dimethyl sulfate (DMS), the marked difference in the amount of material lost, for copper and brass.
Examples B and G also show clearly the good protective action of the quaternary structure, which is at least at the level of that afforded by, for example, benzotriazole (the hydrocarbon-triazole commonly used), as shown by Comparison Example X. Furthermore, the quaternized imidazoles also exhibit an at least equal protec-tive action for other metals (in this case soft solder, steel, gray cast iron and cast aluminum) to that of benzotriazole.
The enhanced protective effect for nonferrous metals of the quaternized imidazoles I employed in accordance with the inven-tion, in comparison with the hydrocarbon-triazoles which are com-monly employed, becomes particularly evident when a test under elevated temperature stress is considered (Table 3). This is the MTU (German Engine and Turbine Union) hot chamber corrosion test, which is normally carried out using specimens of aluminum alloy.
Examples A and B demonstrate the enhanced protective effect rela-tive to Comparison Example X; also evident is the synergy between the quaternized imidazole I and small amounts of hydrocarbon-triazole, which is not so marked in the ASTM D 1384 corrosion test. Once again, the effect of quaternization is revealed when Examples A and B are compared with C and E.
The variables and conditions specified in the examples serve to illustrate the invention and do not constitute any restrictions.

o ~n o 0 0 0 V, O N ~ O N ~O1 1 1 1 1 1 *
r-~1O N .-iO O ~-1 O tf1 O O O O

O N ~ O N ~O1 1 1 i 1 ' 1 r-iO N ~-1O O 3-I

e n O

W O N * O N ~O1 1 1 1 ~ 1 1 r-1O N r-1O O 1-i O tf1 O O O O

A O N ~ O N ~O1 1 1 ~ 1 1 1 *

r-1O N r'1O O S-1 O tn O O O O
'-1 V O N ~ O N ~D1 1 ' I 1 1 1 *
O N e-1O O S-i O In O O O O
~

~ O N * O N ~D1 ' 1 1 1 1 1 ~-iO N .-IO O 1-i N

~f O tf7 O O O M O

.Ll ~ O N ~ O N ~DO '"'~1 1 1 1 1 ~ U

dP ~-1O N ~-1O O O S-1 U

td O

o ~n o o o o x o N ~ o N ~o 1 I 1 1 1 1 r-iO N ~ O O ~1 O

N
-,..i -r-i Cl~

W

O

x ~ Q' U ~ - .i~
-I

-~ 3 ,~

N -,-1 r1 --r-I N
ri -r-1 -ri t~ -,-.I~ .U

U ~ ~ N

y. ~ +~ o ,~ U~

O O U1 +~ cri .N,.i O

U

~ O

N CT O'~

N U

N ~ ~ .p N N
U U 0 0 ~

S-1 'LfU I r O O r r r-I y-,1 -~- -I -I-I

4-t O O .,~-,~ ~ O N N O O O
>~ -ri '-1 .~+~ >CO -riN N f6 c~ N N U
-r-I

+~ cac~3O C 'Otne-Ictj'O 'O ~ tCS>, ~

i-aS-IS.-I~d -r-1ctSO 'O-.~i-r-I 'L3'O

+.~+~ 'ax U +~N -'-IE ~ -~-.~as o~

O 'r-1'J~N c0O ACS~..-rl-r-IN .lr.E 1..1 1 +~'t~'.C.~" .~.,-r'I-rlr-1r-.Ir-I-r-I-r-1O

r-IU S-t~ ~r ~rO ri'-IS~ O
II

D, -r.i~ +.>>t~ .>~N ~,~ N

~ ~ ~ ,~ U ~ O C .i~+.~ctS~ .Crl p O r-I-r-I-rl.1-1tLS-r-IN -r-Ip N 'O .1-~+~

'-I 'Lf'O 'L7W .~'bC ~ '~ ~ -r-IW W .C
N

O O O I N O O I i I E 1 1 +~
~-1 CI~U1 U1N U1U1!xt.-I'-iriH N r-fW
*

H

O O ~-t.-1N N

O O O O O O

~ ~ o o +~~ + + + y n rl W

x U I

.,1 L~

ri M .-iN O

~-1O 01O O rii..1 W O

~-iO O O O O ~..7 I I 1 + + + 4-I

cV M

N
0 0 0 .-1~ N ~ U

00o m o 0 0 ~, I

W

o O o o +

~ f +

y r[

is N

O r-1.-1O N 01 O O O O O O

O
p U

o o o + o o M

I ~

i U .ri N

+~ N M r N ~ ~r3 o ~ 0 0 0 C~ U

.-i O O O O o O

I I I I + +

"'I N
va ' 'a . 0 Lf 3 rlO <-1O M N O ~ O

O O O O O O ~ ~ I

o o o o + t~ + +~ + +

O ~ .-I
.,..I

O +~ -~

O ~-ItnO M O O O

V r-1O O O O O

~ 0 0 o 0 0 o o ~

l ~ x p t u~ o rl r-IN r-1O O v-i47 dP O

b1 O O O O O O

N rl Lf~

O O O O O O

OO + + I -h~+~I

M U

Ca U

~ N

O

H ~

..
~

~ N O ~ U

S-~ .r~ -~--i i O +~ S-1 N ~ ~ M ~ 0 O ~

S-~ U ~ . 1 rl N T3 -ii N N r-I +~

'" -"1 ~ W +~ i W n CLW ~ U ~riu W t U
n H U U ~ ~ ~ ~ O ~ N U

t c C.U E.W
H n f~ 7 H v1 v1 E-~ .,

Claims (22)

CLAIMS:
1. The use of a quaternized imidazole of the general formula I
wherein R1 and R3 independently of one another are saturated or unsaturated hydrocarbon radicals of 1-12 carbon atoms, R2, R4 and R5 independently of one another are hydrogen or saturated or unsaturated hydrocarbon radicals of 1-12 carbon atoms, and X.THETA. is an anion, as a corrosion inhibitor in the corrosion protection of nonferrous metals.
2. The use of claim 1, wherein R1, R2, R3, R4 and R5 are independently substituted with oxygen-functional groups or interrupted by nonadjacent oxygens.
3. The use of claim 1 or 2, wherein R4 and R5, together with the corresponding imidazole carbons, form a five-or six-membered ring.
4. The use as claimed in any one of claims 1 - 3 of quaternized imidazoles I wherein R1 is C1-C4-alkyl, C2-C4-alkenyl, C2-C4-hydroxyalkyl, phenyl-C1-C4-alkyl, phenyl or tolyl, R2 is hydrogen or C1-C4-alkyl, R3 is C1-C4-alkyl or benzyl, R4 and R5 are hydrogen, C1-C4-alkyl or together are a benzo-fused ring, and X.THETA. is a mono-C1-C4-alkyl sulfate anion, half the stoichiometric amount of sulfate or of hydrogen phosphate, dihydrogen phosphate, a third of the stoichiometric amount of phosphate, or nitrate, chloride or bromide.
5. The use as claimed in claim 1 of N-vinylimidazole quaternized with dimethyl sulfate.
6. An antifreeze concentrate based on alkylene glycols or derivatives thereof which comprises 0.0005-2% by weight, based on the total amount of concentrate, of one or more quaternized imidazoles I as set forth in any one of claims 1 to 3.
7. An antifreeze concentrate as claimed in claim 4, which additionally comprises up to 0.3% by weight, based on the total amount of concentrate, of at least one hydrocarbon-triazole or hydrocarbon-thiazole.
8. An antifreeze concentrate as claimed in claim 4 or 5, additionally comprising 0.001-5% by weight, based on the total amount of concentrate, of nonquaternized imidazole or at least one nonquaternized alkyl- or aryl-substituted imidazole.
9. An antifreeze concentrate as claimed in any one of claims 4 to 6, additionally comprising up to 5% by weight, based on the total amount of concentrate, of alkali metal borates or alkali metal phosphates.
10. An antifreeze concentrate as claimed in any one of claims 4 to 7, additionally comprising up to 5% by weight, based on the total amount of concentrate, of at least one aliphatic or aromatic dicarboxylic acid of 4-16 carbon atoms in the form of its alkali metal salts, ammonium salts or amine salts.
11. An antifreeze concentrate as claimed in any one of claims 4 to 8, additionally comprising up to 5% by weight, based on the total amount of concentrate, of at least one aliphatic or aromatic monocarboxylic acid of 3-16 carbon atoms in the form of its alkali metal salts, ammonium salts or amine salts.
12. An antifreeze concentrate as claimed in any one of claims 4 to 9, comprising one or more additional corrosion inhibitors from the group consisting of alkali metal silicates, molybdates, nitrites, nitrates and magnesium nitrate in amounts of in each case up to 1% by weight, based on the total amount of concentrate.
13. An anitfreeze concentrate as claimed in any one of claims 4 to 10, additionally comprising up to 1% by weight, based on the total amount of concentrate, of hard-water stabilizers based on polyacrylic acid, polymaleic acid, acrylic acid-maleic acid copolymers, polyvinylpyrrolidone, polyvinylimidazole, vinylpyrrolidone-vinylimidazole copolymers or copolymers of unsaturated carboxylic acids and olefins.
14. An antifreeze concentrate as claimed in any one of claims 4 to 11 having a pH of 6-11.
15. An antifreeze concentrate as claimed in any one of claims 4 to 12 which is based on ethylene glycol.
16. A ready-to-use aqueous coolant composition of reduced freezing point which comprises water and 10-90% by weight of an antifreeze concentrate as claimed in any one of claims 4 to 13.
17. A method of treating aqueous liquids comprising a water-soluble freezing-point reducer based on alkylene glycols or derivatives thereof to reduce the corrosion of nonferrous metals in contact with the aqueous liquids, which comprises admixing to the aqueous liquids an effective amount of one or more quaternized imidazoles I as set forth in any one of claims 1 to 3.
18. A method of protecting nonferrous metals from corrosion, which comprises using as a corrosion inhibitor a quaternized imidazole of the formula I, wherein R1 and R3 independently of one another are saturated or unsaturated hydrocarbon radicals of 1-12 carbon atoms, R2, R4 and R5 independently of one another are hydrogen or saturated or unsaturated hydrocarbon radicals of 1-12 carbon atoms, and X.THETA. is an anion.
19. The method of claim 18, wherein R1, R2, R3, R4 and R5 are independently substituted with oxygen-functional groups or interrupted by nonadjacent oxygens.
20. The method of claim 18 or 19, wherein R4 and R5, together with the corresponding imidazole carbons, form a five- or six-membered ring.
21. The method as claimed in claim 18, wherein:
R1 is C1-C4-alkyl, C2-C4-alkenyl, C2-C4-hydroxyalkyl, phenyl-C1-C-alkyl, phenyl or tolyl, R2 is hydrogen or C1-C4-alkyl, R3 is C1-C4-alkyl or benzyl, R4 and R5 are hydrogen, C1-C4-alkyl or together are a benzo-fused ring, and x.THETA. is a mono-C1-C4-alkyl sulfate anion, dihydrogen phosphate, nitrate, chloride or bromide, half the stoichiometric amount of sulfate, half the stoichiometric amount of hydrogen phosphate, or a third of the stoichiometric amount of phosphate.
22. The method as claimed in claim 18, which comprises using N-vinylimidazole quaternized with dimethyl sulfate.
CA002234844A 1996-02-15 1997-02-13 Use of quaternized imidazoles as corrosion inhibitors for non-ferrous metals, and coolant compositions and antifreeze concentrates comprising them Expired - Fee Related CA2234844C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19605509A DE19605509A1 (en) 1996-02-15 1996-02-15 Use of quaternized imidazoles as non-ferrous metal corrosion inhibitors and antifreeze concentrates and coolant compositions containing them
DE19605509.1 1996-02-15
PCT/EP1997/000648 WO1997030133A1 (en) 1996-02-15 1997-02-13 Use of quaternized imidazoles as nonferrous metal corrosion inhibitors and antifreeze concentrates and coolant compositions containing said corrosion inhibitors

Publications (2)

Publication Number Publication Date
CA2234844A1 CA2234844A1 (en) 1997-08-21
CA2234844C true CA2234844C (en) 2006-04-04

Family

ID=36143347

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002234844A Expired - Fee Related CA2234844C (en) 1996-02-15 1997-02-13 Use of quaternized imidazoles as corrosion inhibitors for non-ferrous metals, and coolant compositions and antifreeze concentrates comprising them

Country Status (1)

Country Link
CA (1) CA2234844C (en)

Also Published As

Publication number Publication date
CA2234844A1 (en) 1997-08-21

Similar Documents

Publication Publication Date Title
US6045719A (en) Use of quaternized imidazoles as corrosion inhibitors for non-ferrous metals, and coolant compositions and antifreeze concentrates comprising them
US6080331A (en) Glycol based antifreeze concentrates inhibited with monocarboxylic acid salts together with hydrocarbon-triazoles and/or -thiazoles
JPH06116764A (en) Antifreeze composition
JPH02182782A (en) Heat transfer fluid containing dicarboxylic acid mixture as corrosion inhibitor
US6126852A (en) Monocarboxylic acid based antifreeze composition
US20060033076A1 (en) Silicate-free cooling liquids based on organic acids and carbamates having improved corrosion properties
JPH0885782A (en) Antifreeze composition
US6235217B1 (en) Monocarboxylic acid based antifreeze composition
JP3845702B2 (en) Antifreeze / coolant composition
JP2916721B2 (en) Coolant composition
US5071580A (en) Pumpable corrosion inhibitor slurries suitable for charging cooling system filters
CA2234844C (en) Use of quaternized imidazoles as corrosion inhibitors for non-ferrous metals, and coolant compositions and antifreeze concentrates comprising them
JPH04117481A (en) Antifreeze
JP4119622B2 (en) Coolant composition
JP2002520442A (en) Antifreeze concentrate and coolant composition comprising the antifreeze concentrate for cooling circulation of an internal combustion engine
JP3814793B2 (en) Antifreeze composition
JP4616536B2 (en) Antifreeze / coolant composition
JPWO2005037950A1 (en) Coolant composition
JP2000219981A (en) Antifreezing solution composition
JP2004068155A (en) Antifreeze
JPH1046134A (en) Antifreeze composition
CN108997984A (en) Liquid, preparation method and application are added in radiator protection
JP2008088242A (en) Cooling liquid composition
JP2000219876A (en) Antifreezing fluid composition
JPWO2006046275A1 (en) Antifreeze / coolant composition

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed