CA1178578A - Cyclic amidine based corrosion inhibitors which inhibit corrosion caused by co.sub.2 and h.sub.2s - Google Patents
Cyclic amidine based corrosion inhibitors which inhibit corrosion caused by co.sub.2 and h.sub.2sInfo
- Publication number
- CA1178578A CA1178578A CA000397859A CA397859A CA1178578A CA 1178578 A CA1178578 A CA 1178578A CA 000397859 A CA000397859 A CA 000397859A CA 397859 A CA397859 A CA 397859A CA 1178578 A CA1178578 A CA 1178578A
- Authority
- CA
- Canada
- Prior art keywords
- corrosion
- water
- oil
- composition
- sub
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/54—Compositions for in situ inhibition of corrosion in boreholes or wells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Lubricants (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
Abstract of the Disclosure The invention relates to corrosion inhibitors which are amides of cyclic amidines. The inhibitors are particularly useful for preventing the corrosion of metals caused by H2S and CO2 in water-in-oil, particularly in saltwater-in-oil emulsions.
Description
~7~3~i'7~3 CYCLIC AMIDINE BASED CORROSION INHIBITORS
WHICH INHIBIT CORROSION CAUSED BY C2 A~lD H2S
Background of the Invention 1. Field of the Invention The invention relates to corrosion inhibitors which are amides of cyclic amidines. The inhibitors are particularly useful for preventing the corrosion of metals caused by H2S and CO2 ("acid gas") in water-in-oil, particularly in saltwater-in-oil emulsions.
WHICH INHIBIT CORROSION CAUSED BY C2 A~lD H2S
Background of the Invention 1. Field of the Invention The invention relates to corrosion inhibitors which are amides of cyclic amidines. The inhibitors are particularly useful for preventing the corrosion of metals caused by H2S and CO2 ("acid gas") in water-in-oil, particularly in saltwater-in-oil emulsions.
2. Description of the Prior Art It is known to inject a solution or dispersion of corrosion inhibitors in the crude oil during oil recovery, and in the transport or storage of the crude oil so that a protective layer forms on the surface of the metal parts coming in contact with the oil. The crude oil emulsions usually contain saltwater and in many cases, depending upon the origin of the oil, contain H2S and CO2 which have a pro-nounced corrosive effect. The corrosion inhibitors to be used for this purpose should be soluble in oil and should at least be dispersible in saltwater so that they can have an optimum effect.
Such systems are known from German published application 2,846,977. These are imidazolinium salts which are used dissolved in an oil soluble organic solvent in the presence of a hydrocarbon oil. The problems with such 4~
~17~5~3 systems are the relatively complicated metering form l3 components) and the fact that the corrosion protection is not satisfactory in all cases. We have noted, for instance, that the imidazoline having the formula ~ N - CH2 (as chloride) described in the referenced publication does not develop sufficient effectiveness against the corrosive erosion caused by the effects of H2S when used alone.
Summary of the Invention The subject invention relates to compounds having the following structural formula:
~ N-(CH2)n HC
N -CH O
2 ll CH2--~CH2 ~ NH-C-R
in which R denotes C7- to C25-, preferably C8- to C17-alkyl or alkenyl radical and n represents the numbers 1 or 2 .
The present invention also provides a composition comprising a mixture of the above compounds and from 0.5 to 100 percent by weight of elementary sulfur relative to the above compounds.
In accordance with the present invention, n may be 1 and R may be selected from the group consisting of C8H17 ; C17H33, CllH23 and C7H15.
~ - 2 -The subject ccmpounds and compositions are p~ticularly useful as corrosion inhibitors in pre~entin~ the corrosion of metal caused by H2S and C02 in water-in-oil emulsions such as crude oil.
The compounds and cc~positions can be uni~o ~ y distributed in oil-in-water emulsions without the aid of additional solvents.
~escription of the Preferred Embodiments -The subject compounds are amides of cyclic amidines which are based upon an imidazoline- or 3,5-tetrahydro-pyrimidine system. The compounds can be obtained in a simple manner by traditional reactions.
Initially a carboxylic acid R-COOH, with R
representing a C7- to C25-, preferahly C8- to C17- alkyl or alkenyl radical is reacted with diethylene triamine or di-n-propylene triamine at 120C to 1~0C within 5 to 10 hours in a mole ratio of 1:1 to 1:1O2 and the resultant acid amide is reacted with formamide at 120C to 150C within 0.5 to 2 hours. Following this process the product is condensed at 200C to 300C preferably under vacuum (1.5 mbars to 80 mbars) within a period of 5 to 10 hours. The resultant imidazoline and/or tetrahydro-pyrimidine derivatives may be isolated in their pure form.
All of the above defined carboxylic acids are suitable as starting carhoxylic acids. Preferably chosen are, for instance, n-octanic acid, iso-octanic acid (2-ethylhexanoic acid), iso-nonanoic acid (3,5,5-trimethylhexanic acid), lauric acid, stearic acid, oleicacid, behenic acid and mixtures thereof. Mixtures of natural fatty acids such as tallow fatty acid, coconut fatty acid, colza oil fatty acid and palm kernel fatty acid are also suitable.
The compounds alone have a very satisfac~ory effect as inhibitors against H2S and CO2 corrosion. Testing indicates that corrosion is less than a fourth of the value obtained when the compounds are not used.
The inhibition effect can be increased, however, if 0.5 to 100 percent by weight preferably 1 to 30 percent by weight of colloidal sulfur is present relative to amides of the cyclic amidine. The sulfur can be incorporated in this system by a mere admixing of "colloidal" sulfur but is preferahly incorporated by heating the mixture to 100C to 200C within a period of 1 to 3 hours. Inhibitors obtained in this manner are capable of reducing the corrosion to less than one-fifth of the value obtained when the inhibitors are not used.
The subject corrosion inhibitors are added to the water-in-oil emulsions in quantities of 50 ppm to 1000 ppm relative to the weight of the emulsion. They disperse without difficulties in the aqueous as well as in the oil phase.
The following examples will illustrate in detail the invention, but are not intended to limit the scope of its application.
Examples Examples 1 and 2 illustrate how the corrosion inhibitors of the subject invention are prepared.
Example 1 In a reaction vessel, 423.7 grams of oleic acid are heated to a temperature of 70C to 80C and at this temperature are added dropwise into 170.3 grams of diethylenetriamine. E'ollowing this, reaction water is removed by distillation at 150C to 160C for 7 to 8 hours. Then 67.6 grams of formamide are added dropwise into the resultant acid amide at 120C to 150C within a period of 1 hour. Subsequently the mixture is condensed at 200C
to 250C under a vacuum of approximately 20 Torr for 8 hours. The compound had a structure of /~N- CE32 HC
N--CH2 o ( ?
wherein R = C17 H33 . The yield was 565 grams of a brown viscous oil.
Examp_e 2_ In a reaction vessel, 316.~ grams of isononamic acid (3,5,5-trimethylhexanic acid) are heated to a tempera-ture of 70C to 80C and are added dropwise into 288.7 grams of ~ipropylenetriamine at this temperature. Following this process, reaction water is removed by distillation at 150C
to 160C for 7 to 8 hours. Then 90 grams of formamide are added dropwise into the resultant acid amide at 120C to 150C within a period of 30 minutes. Followiny this, the product is condensed at 200C to 250C and under vacuum of approximately 20 Torrs separating ammonium. The compound had a structure of IIC ~ ` CH2 wherein R = C8H17 . The yield was 560 grams of brown viscous oil.
The corrosion inhihitors and several variations thereof were tested according to the so-called dynamic or "wheel" test. This is a method commonly employed in the crude oil recovery to test inhibitors.
The test samples are iron sheet metal having the dimensions of 130 mm x 10 mm x 1 mm. These are sanded, '^7~' i' f~
degreased with toluene, and are weighed. Test gasoline was used as the test medium which contained 50 percent by weight of saltwater wit}l 3 percent ~aCi in emulsified form. In order to simulate field conditions, the test medium was saturated with H2S and CO2 and was poured into test bot-tles. Following this the inhibitors to be tested were added in ~uantities of 250 ppm. The test samples of sheet metals were fastened to the bottle covers and were immersed in the test medium.
The test bottles were then fastened to a rotating axis (wheel) which turned in a water bath maintained at 80C
at a speed of 40 rpm. The test duration was 16 hours.
Thereafter, the test strips were cleaned with an inhibiting acid~ were degreased, dried and were weighed in order to determine the weight losses. The results were evaluated and compared with a blank value (test without added inhibitor).
The specific corrosion inhibitors used and the results are shown in the following table.
11'7~5t7~
TABLE
Compound Corrosion of Formula R (m~/sample) 17 33 22.9 17 35 22.5 II C17H33 22.4 II C17H35 21.1 I + 1/5/10 ~ S C17H33 21.9/21.2/17.4 I + 1/5/10 % S C17H35 22.4/22.7/26.9 II + 1/5/10 % S C17H33 28.6/26.9/23.3 7 17 35.5 8 17 33.8 11 23 28.2 17 33 22.9 17 35 22.5 I Tallow fatty acid radical 26.4 I Coconut fatty acid radi Ql 24.9 I Crude oil fatty acid radical20.2 I Etalm kernel fatty acid radical 23.4 II 7 15 34.8 II 8 17 29.3 II CllH33 27.1 II C17H33 21.1 II C17H33 22.4 II Tallow fatty acid radical 24.2 II Coconut fatty acid radical 26.1 II Colza oil fatty acid radical21.3 II Palm kernel fatty acid radical 22.7 Blank value (without sulfur) 98.3 " " (with 10 percent sulfur) 114.9 Comparison*
¦ N CH~ ~
N - CH ~ [ ~ 52.8 L CH2CH2-0~
* In accordance with Germany pu~lished application 2,846,977.
Such systems are known from German published application 2,846,977. These are imidazolinium salts which are used dissolved in an oil soluble organic solvent in the presence of a hydrocarbon oil. The problems with such 4~
~17~5~3 systems are the relatively complicated metering form l3 components) and the fact that the corrosion protection is not satisfactory in all cases. We have noted, for instance, that the imidazoline having the formula ~ N - CH2 (as chloride) described in the referenced publication does not develop sufficient effectiveness against the corrosive erosion caused by the effects of H2S when used alone.
Summary of the Invention The subject invention relates to compounds having the following structural formula:
~ N-(CH2)n HC
N -CH O
2 ll CH2--~CH2 ~ NH-C-R
in which R denotes C7- to C25-, preferably C8- to C17-alkyl or alkenyl radical and n represents the numbers 1 or 2 .
The present invention also provides a composition comprising a mixture of the above compounds and from 0.5 to 100 percent by weight of elementary sulfur relative to the above compounds.
In accordance with the present invention, n may be 1 and R may be selected from the group consisting of C8H17 ; C17H33, CllH23 and C7H15.
~ - 2 -The subject ccmpounds and compositions are p~ticularly useful as corrosion inhibitors in pre~entin~ the corrosion of metal caused by H2S and C02 in water-in-oil emulsions such as crude oil.
The compounds and cc~positions can be uni~o ~ y distributed in oil-in-water emulsions without the aid of additional solvents.
~escription of the Preferred Embodiments -The subject compounds are amides of cyclic amidines which are based upon an imidazoline- or 3,5-tetrahydro-pyrimidine system. The compounds can be obtained in a simple manner by traditional reactions.
Initially a carboxylic acid R-COOH, with R
representing a C7- to C25-, preferahly C8- to C17- alkyl or alkenyl radical is reacted with diethylene triamine or di-n-propylene triamine at 120C to 1~0C within 5 to 10 hours in a mole ratio of 1:1 to 1:1O2 and the resultant acid amide is reacted with formamide at 120C to 150C within 0.5 to 2 hours. Following this process the product is condensed at 200C to 300C preferably under vacuum (1.5 mbars to 80 mbars) within a period of 5 to 10 hours. The resultant imidazoline and/or tetrahydro-pyrimidine derivatives may be isolated in their pure form.
All of the above defined carboxylic acids are suitable as starting carhoxylic acids. Preferably chosen are, for instance, n-octanic acid, iso-octanic acid (2-ethylhexanoic acid), iso-nonanoic acid (3,5,5-trimethylhexanic acid), lauric acid, stearic acid, oleicacid, behenic acid and mixtures thereof. Mixtures of natural fatty acids such as tallow fatty acid, coconut fatty acid, colza oil fatty acid and palm kernel fatty acid are also suitable.
The compounds alone have a very satisfac~ory effect as inhibitors against H2S and CO2 corrosion. Testing indicates that corrosion is less than a fourth of the value obtained when the compounds are not used.
The inhibition effect can be increased, however, if 0.5 to 100 percent by weight preferably 1 to 30 percent by weight of colloidal sulfur is present relative to amides of the cyclic amidine. The sulfur can be incorporated in this system by a mere admixing of "colloidal" sulfur but is preferahly incorporated by heating the mixture to 100C to 200C within a period of 1 to 3 hours. Inhibitors obtained in this manner are capable of reducing the corrosion to less than one-fifth of the value obtained when the inhibitors are not used.
The subject corrosion inhibitors are added to the water-in-oil emulsions in quantities of 50 ppm to 1000 ppm relative to the weight of the emulsion. They disperse without difficulties in the aqueous as well as in the oil phase.
The following examples will illustrate in detail the invention, but are not intended to limit the scope of its application.
Examples Examples 1 and 2 illustrate how the corrosion inhibitors of the subject invention are prepared.
Example 1 In a reaction vessel, 423.7 grams of oleic acid are heated to a temperature of 70C to 80C and at this temperature are added dropwise into 170.3 grams of diethylenetriamine. E'ollowing this, reaction water is removed by distillation at 150C to 160C for 7 to 8 hours. Then 67.6 grams of formamide are added dropwise into the resultant acid amide at 120C to 150C within a period of 1 hour. Subsequently the mixture is condensed at 200C
to 250C under a vacuum of approximately 20 Torr for 8 hours. The compound had a structure of /~N- CE32 HC
N--CH2 o ( ?
wherein R = C17 H33 . The yield was 565 grams of a brown viscous oil.
Examp_e 2_ In a reaction vessel, 316.~ grams of isononamic acid (3,5,5-trimethylhexanic acid) are heated to a tempera-ture of 70C to 80C and are added dropwise into 288.7 grams of ~ipropylenetriamine at this temperature. Following this process, reaction water is removed by distillation at 150C
to 160C for 7 to 8 hours. Then 90 grams of formamide are added dropwise into the resultant acid amide at 120C to 150C within a period of 30 minutes. Followiny this, the product is condensed at 200C to 250C and under vacuum of approximately 20 Torrs separating ammonium. The compound had a structure of IIC ~ ` CH2 wherein R = C8H17 . The yield was 560 grams of brown viscous oil.
The corrosion inhihitors and several variations thereof were tested according to the so-called dynamic or "wheel" test. This is a method commonly employed in the crude oil recovery to test inhibitors.
The test samples are iron sheet metal having the dimensions of 130 mm x 10 mm x 1 mm. These are sanded, '^7~' i' f~
degreased with toluene, and are weighed. Test gasoline was used as the test medium which contained 50 percent by weight of saltwater wit}l 3 percent ~aCi in emulsified form. In order to simulate field conditions, the test medium was saturated with H2S and CO2 and was poured into test bot-tles. Following this the inhibitors to be tested were added in ~uantities of 250 ppm. The test samples of sheet metals were fastened to the bottle covers and were immersed in the test medium.
The test bottles were then fastened to a rotating axis (wheel) which turned in a water bath maintained at 80C
at a speed of 40 rpm. The test duration was 16 hours.
Thereafter, the test strips were cleaned with an inhibiting acid~ were degreased, dried and were weighed in order to determine the weight losses. The results were evaluated and compared with a blank value (test without added inhibitor).
The specific corrosion inhibitors used and the results are shown in the following table.
11'7~5t7~
TABLE
Compound Corrosion of Formula R (m~/sample) 17 33 22.9 17 35 22.5 II C17H33 22.4 II C17H35 21.1 I + 1/5/10 ~ S C17H33 21.9/21.2/17.4 I + 1/5/10 % S C17H35 22.4/22.7/26.9 II + 1/5/10 % S C17H33 28.6/26.9/23.3 7 17 35.5 8 17 33.8 11 23 28.2 17 33 22.9 17 35 22.5 I Tallow fatty acid radical 26.4 I Coconut fatty acid radi Ql 24.9 I Crude oil fatty acid radical20.2 I Etalm kernel fatty acid radical 23.4 II 7 15 34.8 II 8 17 29.3 II CllH33 27.1 II C17H33 21.1 II C17H33 22.4 II Tallow fatty acid radical 24.2 II Coconut fatty acid radical 26.1 II Colza oil fatty acid radical21.3 II Palm kernel fatty acid radical 22.7 Blank value (without sulfur) 98.3 " " (with 10 percent sulfur) 114.9 Comparison*
¦ N CH~ ~
N - CH ~ [ ~ 52.8 L CH2CH2-0~
* In accordance with Germany pu~lished application 2,846,977.
Claims (14)
1. A compound having the following structural formula:
in which R represents a C7- to C25- alkyl or alkenyl radical and in which n represents the numbers 1 or 2.
in which R represents a C7- to C25- alkyl or alkenyl radical and in which n represents the numbers 1 or 2.
2. A composition comprising the product prepared by mixing the compound of claim 1 with elementary sulfur such that from 0.5 to 100 percent by weight of sulfur is present relative to the compound of claim 1.
3. The composition of claim 2 wherein the sulfur and compound of claim 1 are heated to 100°C to 200°C
within a period of 1 to 3 hours.
within a period of 1 to 3 hours.
4. A process for inhibiting the corrosion of metals caused by H2S and CO2 in water-in-oil emulsions comprising adding, as corrosion inhibitor, a compound of claim 1, to a water-in oil emulsion.
5. A process for inhibiting the corrosion of metals caused by H2S and CO2 in water-in-oil emulsions comprising adding, as corrosion inhibitor, a compound of claim 1, to a water-in-oil emulsion and wherein from 50 ppm to 1000 ppm of said corrosion inhibitor are used relative to the weight or emulsion.
6. A process for inhibiting the corrosion of metals caused by H2S and CO2 in water-in-oil emulsions comprising adding, as corrosion inhibitor, a composition of claim 2, to a water-in-oil emulsion.
7. A process for inhibiting the corrosion of metals caused by H2S and CO2 in water-in-oil emulsions comprising adding, as corrosion inhibitor, a composition of claim 2, to a water-in-oil emulsion and wherein from 50 ppm to 1000 ppm of said corrosion inhibitor are used relative to the weight of emulsion.
8. A process for inhibiting the corrosion of metals caused by H2S and CO2 in water-in-oil emulsions comprising adding, as corrosion inhibitor, a composition of claim 3, to a water-in-oil emulsion.
9. A process for inhibiting the corrosion of metals caused by H2S and CO2 in water-in-oil emulsions comprising adding, as corrosion inhibitor, a composition of claim 3, to a water-in-oil emulsion and wherein from 50 ppm to 1000 ppm of said corrosion inhibitor are used relative to the weight of emulsion.
10. The compound of claim 1 wherein n is 1 and R is selected from the group consisting of -C8H17, -C17H33, C11H23 and C7H15.
11. The composition of claim 2 wherein n is 1 and R is selected from the group consisting of -C8H17, -C17H33, C11H23 and C7H15.
12. The composition of claim 3 wherein n is 1 and R is selected from the group consisting of -C8H17, -C17H33, C11H23 and C7H15.
13. The process of any one of claims 4, 5 and 6, wherein n is 1 and R is selected from the group con-sisting of -C8H17, -C17H33, C11H23 and C7H15.
14. The process of any one of claims 7, 8 and 9, wherein n is 1 and R is selected from the group consisting of -C8H17, -C17H33, C11H23 and C7H15.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813109826 DE3109826A1 (en) | 1981-03-14 | 1981-03-14 | INHIBITORS AGAINST THE CORROSION OF H (DOWN ARROW) 2 (DOWN ARROW) S AND CO (DOWN ARROW) 2 (DOWN ARROW) IN WATER-IN-OIL EMULSIONS |
| DEP3109826.6 | 1981-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1178578A true CA1178578A (en) | 1984-11-27 |
Family
ID=6127231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000397859A Expired CA1178578A (en) | 1981-03-14 | 1982-03-08 | Cyclic amidine based corrosion inhibitors which inhibit corrosion caused by co.sub.2 and h.sub.2s |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0060456B1 (en) |
| CA (1) | CA1178578A (en) |
| DE (2) | DE3109826A1 (en) |
| NO (1) | NO155439C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5746946A (en) * | 1995-02-21 | 1998-05-05 | King Idustries, Inc. | Imidazolidinone derivatives as corrosion inhibitors |
| US10221368B2 (en) | 2015-07-27 | 2019-03-05 | Instituto Mexicano Del Petroleo | Method of inhibiting corrosion using a corrosion inhibitor derived from vegetable oils |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6077460A (en) * | 1996-07-17 | 2000-06-20 | Basf Aktiengesellschaft | Corrosion inhibition |
| DE19628893A1 (en) * | 1996-07-17 | 1998-01-22 | Basf Ag | Use of 1-amidoalkylimidazoles as corrosion inhibitors in the petrochemical industry and process for their preparation |
| EP0906969A1 (en) * | 1997-10-01 | 1999-04-07 | Degussa Aktiengesellschaft | Procces and composition for inhibiting corrosion |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2133723A1 (en) * | 1971-07-07 | 1973-01-25 | Texaco Development Corp | Corrosion inhibitors for metals - consisting of salts of imidazolines and carboxylic acids |
| US4101441A (en) * | 1975-12-29 | 1978-07-18 | Chemed Corporation | Composition and method of inhibiting corrosion |
| CA1083335A (en) * | 1976-05-10 | 1980-08-12 | Chemed Corporation | Composition and method of inhibiting corrosion |
| US4238350A (en) * | 1977-11-16 | 1980-12-09 | Malaco Ag | Method and a composition for inhibiting corrosion |
-
1981
- 1981-03-14 DE DE19813109826 patent/DE3109826A1/en not_active Withdrawn
-
1982
- 1982-03-05 EP EP82101715A patent/EP0060456B1/en not_active Expired
- 1982-03-05 DE DE8282101715T patent/DE3261578D1/en not_active Expired
- 1982-03-08 CA CA000397859A patent/CA1178578A/en not_active Expired
- 1982-03-12 NO NO820814A patent/NO155439C/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5746946A (en) * | 1995-02-21 | 1998-05-05 | King Idustries, Inc. | Imidazolidinone derivatives as corrosion inhibitors |
| US10221368B2 (en) | 2015-07-27 | 2019-03-05 | Instituto Mexicano Del Petroleo | Method of inhibiting corrosion using a corrosion inhibitor derived from vegetable oils |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3261578D1 (en) | 1985-01-31 |
| DE3109826A1 (en) | 1982-09-23 |
| EP0060456A1 (en) | 1982-09-22 |
| EP0060456B1 (en) | 1984-12-19 |
| NO155439B (en) | 1986-12-22 |
| NO155439C (en) | 1987-04-01 |
| NO820814L (en) | 1982-09-15 |
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