Polyester polyamine and polyester polyquaternary ammonium corrosion inhibitors
The present invention relates to the use of a product obtainable by the reaction of a fatty acid, or mixture of acids, having the formula R 1 COOH (I); and a dicarboxylic acid or a derivative thereof having the formula (IIa) or (IIb) with an alkoxylated fatty amine having the formula (III) or a partial or wholly quaternized derivative thereof; optionally said reaction between the fatty acid, the dicarboxylic acid and the alkoxylated fatty amine is being followed by a further reaction step wherein part or all of the nitrogen atoms are quaternized by reaction with an alkylating agent R 5 X; as a corrosion inhibitor for metal surfaces. The present invention also relates to such products and to methods for their production.
1. A method for protecting a metal surface from corrosion by contacting the metal surface with a product obtainable by the reaction of
a fatty acid, or mixture of acids, having the formula R 1 COOH (I), where R 1 CO is an acyl group having 8 to 24 carbon atoms, that may be saturated or unsaturated, linear or branched; and
a dicarboxylic acid or a derivative thereof having the formula (IIa) or (IIb)
where D is —OH, —Cl, or —OR 3 , where R 3 is a C 1 -C 4 alkyl group; R2 is selected from the group consisting of a direct bond, an alkylene radical of formula —(CH 2 ) z —, in which z is an integer from 1 to 10, a substituted alkylene radical wherein said alkylene radical is substituted by 1 or 2 —OH groups, a cycloalkylene, a cycloalkenylene and/or an arylene group;
with an alkoxylated fatty amine having the formula (III)
wherein R 4 is a hydrocarbyl group having 8-24 carbon atoms; AO is an alkyleneoxy group containing 2-4 carbon atoms, each B is, independently, an alkyl group having 1-4 carbon atoms, or a benzyl group; each n is, independently, at least 1 and the sum of all n is 2-30; s is 2 or 3; and y is 0 or 1; or of a product obtainable by partial or total quaternisation of the alkoxylated fatty amine of formula (III).
2. The method according to claim 1 wherein the alkoxylated fatty amine has the formula
wherein each x independently is a number between 1 and 5, and Σx on molar average is a number between 2 and 10, AO is an alkyleneoxy group having 2-4 carbon atoms, R 4 is a C 8 -C 24 alkyl group, or a partial or wholly quaternised derivative thereof.
3. The method according to claim 2 wherein the product has the formula
where R 1 , AO, x, R2, and R 4 have the same meaning as in claim 2 ; R 5 is a hydrocarbyl group, and X − is an anion derived from the alkylating agent R 5 X; t is a number 0 or 1; and p is a number within the range 1-15, and is on average at least 1.
4. The method according to claim 1 , wherein R 1 CO is an acyl group having 16 to 24 carbon atoms.
5. The method according to claim 1 , wherein R2 is an alkylene radical of formula —(CH 2 ) z —, in which z is 4.
6. The method according to claim 2 wherein x=1.
7. The method according to claim 3 , wherein t=1.
8. The method according to claim 7 wherein R 5 is a C 1 -C 4 alkyl group or the benzyl group.
9. The method according to claim 7 , wherein the alkylating agent R 5 X is chosen from the group consisting of methyl chloride, methyl bromide, dimethyl sulphate, diethyl sulphate, dimethyl carbonate and benzyl chloride.
10. The method according to claim 1 , wherein the molar ratio between the fatty acid, or mixture of acids, of structure (I) and the alkoxylated fatty amine (III) in the reaction mixture is 1:1.2 to 1:10, and the molar ratio between the fatty acid, or mixture of acids, of structure (I) and the dicarboxylic acid or derivative (IIa) or (IIb) is 2:1 to 1:8.
11. The method according to claim 1 , wherein the metal surfaces are part of pipelines, pumps, tanks and other equipment used in oil and gas fields or oil refineries.
12. The method according to claim 1 , wherein the corrosion inhibiting product is added to a flowing liquid at any point in a flow line upstream of the point or line that are intended to be protected.
13. A product obtainable by the reaction of
a fatty acid, or mixture of acids, having the formula R 1 COOH (I), where R 1 CO is an acyl group having 8 to 24 carbon atoms, that may be saturated or unsaturated, linear or branched; and
a dicarboxylic acid or a derivative thereof having the formula (IIa) or (IIb)
where D is —OH, —Cl, or —OR 3 , where R 3 is a C 1 -C 4 alkyl group; R2 is selected from the group consisting of a direct bond, an alkylene radical of formula —(CH 2 ) z —, in which z is an integer from 1 to 10, a substituted alkylene radical wherein said alkylene radical is substituted by 1 or 2 —OH groups, a cycloalkylene, a cycloalkenylene and/or an arylene group;
with an alkoxylated fatty amine having the formula (III)
wherein R 4 is a hydrocarbyl group having 8-24 carbon atoms; AO is an alkyleneoxy group containing 2-4 carbon atoms; each B is, independently, an alkyl group having 1-4 carbon atoms, or a benzyl group; each n is, independently, at least 1 and the sum of all n is 2-30; s is 2 or 3; and y is 0 or 1; or a product obtainable by partial or total quaternisation of the alkoxylated fatty amine of formula (III).
14. A method for producing the product of claim 13 by reacting a compound having formula (I) and (IIa) or (IIb) with (III).
15. The product according to claim 13 wherein the alkoxylated fatty amine has the formula
wherein each x independently is a number between 1 and 5, and Σx on molar average is a number between 2 and 10, AO is an alkyleneoxy group having 2-4 carbon atoms, R 4 is a C 8 -C 24 alkyl group, or a partial or wholly quaternised derivative thereof.
16. The product according to claim 15 wherein the product has the formula
where R 1 , AO, x, R2, and R 4 have the same meaning as in claim 2 ; R 5 is a hydrocarbyl group, and X − is an anion derived from the alkylating agent R 5 X; t is a number 0 or 1; and p is a number within the range 1-15, and is on average at least 1.
17. The product according to claim 13 , wherein R 1 CO is an acyl group having 16 to 24 carbon atoms.
18. The product according to claim 13 , wherein R2 is an alkylene radical of formula —(CH 2 ) z —, in which z is 4.
19. The product according to claim 15 wherein x=1.
20. The product according to claim 16 , wherein t=1.
21. The product according to claim 20 wherein R 5 is a C 1 -C 4 alkyl group or the benzyl group.
22. The product according to claim 20 , wherein the alkylating agent R 5 X is chosen from the group consisting of methyl chloride, methyl bromide, dimethyl sulphate, diethyl sulphate, dimethyl carbonate and benzyl chloride.
23. The product according to claim 13 , wherein the molar ratio between the fatty acid, or mixture of acids, of structure (I) and the alkoxylated fatty amine (III) in the reaction mixture is 1:1.2 to 1:10, and the molar ratio between the fatty acid, or mixture of acids, of structure (I) and the dicarboxylic acid or derivative (IIa) or (IIb) is 2:1 to 1:8.
24. The method of claim 1 wherein the reaction between the fatty acid, the dicarboxylic acid and the alkoxylated fatty amine is followed by a further reaction step wherein part or all of the nitrogen atoms are quaternised by reaction with an alkylating agent R 5 X, where R 5 is a hydrocarbyl group, and X − is an anion derived from the alkylating agent R 5 X.
25. The method of claim 2 wherein the reaction between the fatty acid, the dicarboxylic acid and the alkoxylated fatty amine is followed by a further reaction step wherein part or all of the nitrogen atoms are quaternised by reaction with an alkylating agent R 5 X, where R 5 is a hydrocarbyl group, and X − is an anion derived from the alkylating agent R5X.
26. The product of claim 13 obtainable by the reaction wherein the reaction between the fatty acid, the dicarboxylic acid and the alkoxylated fatty amine is followed by a further reaction step wherein part or all of the nitrogen atoms are quaternised by reaction with an alkylating agent R 5 X, where R 5 is a hydrocarbyl group, and X − is an anion derived from the alkylating agent R 5 X.
27. The method of claim 14 further comprising reacting the product obtained by reacting a compound having formula (I) and (IIa) or (IIb) with (III)-with an alkylating agent R 5 X, where R 4 is a hydrocarbyl group and X − is an anion derived from the alkylating agent R 5 X.
28. The product of claim 15 obtainable by the reaction wherein the reaction between the fatty acid, the dicarboxylic acid and the alkoxylated fatty amine is followed by a further reaction step wherein part or all of the nitrogen atoms are quaternised by reaction with an alkylating agent R 5 X, where R 5 is a hydrocarbyl group, and X − is an anion derived from the alkylating agent R5X.