Organic salts of glyceride-cyclic carboxylic acid anhydride adducts as corrosion inhibitors

Patent metadata

Field	Value
Publication number	US-9688605-B2
Application number	US-201415103119-A
Country	US
Kind code	B2
Filing date	Dec 5, 2014
Priority date	Dec 10, 2013
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

Abstract

A corrosion-inhibiting composition includes a diluent and a mixture of organic salts of half ester-half acids of a dioic acid with of a glyceride group with a fatty acyl residue. Included are organic salts of glyceride-cyclic carboxylic acid anhydride adducts.

First claim

What is claimed is:

1. A corrosion-inhibiting composition comprising a diluent and a mixture of organic salts of half ester-half acids having the general structure of STRUCTURE (1) at a total concentration of from 0.01-30 wt. % of the composition:

where:
n is from 0-2;
G is a glyceride residue comprising a mixture of:

each FA is a straight-chain fatty acyl residue having from 4 to 24 carbon atoms and from 0 to 3 double bonds in the carbon chain;
R 1 and R 2 are independently selected from hydrogen, straight-chain or branched alkyl or alkenyl groups having from 1-18 carbon atoms or where R 1 and R 2 together with the two carbons atoms to which they attach and the —(CH 2 ) n — group form a cyclic structure having at least 5 carbon atoms; and
A is a neutralizing group which comprises an ammonium ion or a protonated organic base selected from the group consisting of protonated amines, alkylamines, alkanolamines, imidazoles, alkylimidazoles, and combinations thereof.

2. The composition of claim 1 , wherein n is 0.

3. The composition of claim 1 , wherein the mixture of organic salts of half ester-half acids having the general structure of STRUCTURE (1) is at a total concentration of at least 1 wt. % of the composition.

4. The composition of claim 1 , wherein the mixture of organic salts of half ester-half acids having the general structure of STRUCTURE (1) is at a total concentration of up to 10 wt. % of the composition.

5. The composition of claim 1 , wherein the diluent is selected from water, volatile organic solvents, oils, and combinations thereof.

6. The composition of claim 5 , wherein the volatile organic solvent is selected from aliphatic and aromatic hydrocarbons, alcohols, glycols, toluene, terpenoids, terpenes, esters, ethers, acetals, polar aprotic solvents, ketones, and derivatives and combinations thereof.

7. The composition of claim 1 , wherein the composition is in the form of an emulsion.

8. The composition of claim 1 , wherein the diluent is present in the composition at a total concentration of at least 50 wt. %.

9. The composition of claim 1 , wherein at least some of the fatty acyl residues are derived from a vegetable oil.

10. The composition of claim 9 , wherein the vegetable oil has less than 20 wt. % saturated fatty acids.

11. The composition of claim 1 , wherein the fatty acyl residues have an average of greater than 14 carbon atoms.

12. The composition of claim 1 , wherein the protonated organic base comprises a protonated amine.

13. The composition of claim 1 , wherein the protonated organic base is selected from the group consisting of 2-(2-aminoethoxy)ethanol; 5-amino-1-pentanol; 3-amino-1-propanol; 2-(2-aminoethoxy)ethanol; N,N-diethylethanolamine; 3-dimethylamino-1-propylamine; N,N-dimethylethanolamine; monoethanolamine; 2-ethylhexylamine; imidazole; 3-isododecyloxy-1-propylamine; 3-methoxypropylamine; 1-methylimidazole; 2-methylimidazole; tributylamine; triethanolamine; triisopropanolamine; a mixture of C 10 -C 15 tert-alkyl primary amines; and combinations thereof.

14. The composition of claim 1 , wherein an average number of FA groups per glyceride residue G in the mixture is at least 1.

15. The composition of claim 1 , wherein an average molecular weight of organic salts in the mixture is less than 1250 g/mole.

16. The composition of claim 1 , wherein when n is 0, at least one of R 1 and R 2 is not hydrogen.

17. A corrosion-inhibiting composition comprising a diluent and a mixture of organic salts of half ester-half acids having the general structure of STRUCTURE (1) at a total concentration of from 0.01-30 wt. % of the composition:

where:
n is from 0-2;
G is a glyceride residue comprising a mixture of:

each FA is a straight-chain fatty acyl residue having from 4 to 24 carbon atoms and from 0 to 3 double bonds in the carbon chain, wherein at least some of the fatty acyl residues are derived from an unhydrogenated vegetable oil;
R 1 and R 2 are independently selected from hydrogen, straight-chain or branched alkyl or alkenyl groups having from 1-18 carbon atoms or where R 1 and R 2 together with the two carbons atoms to which they attach and the —(CH 2 ) n — group form a cyclic structure having at least 5 carbon atoms; and
A is a neutralizing group.

18. The composition of claim 17 , wherein the neutralizing group comprises at least one of a protonated organic base, a metal cation, and an ammonium ion.

19. The composition of claim 18 , wherein the neutralizing group comprises a protonated organic base selected from the group consisting of protonated amines, alkylamines, alkanolamines, imidazoles, alkylimidazoles; and combinations thereof.

20. A method of inhibiting corrosion of a metallic surface in contact with a corrosive environment, the method comprising:
contacting the surface with a corrosion-inhibiting composition comprising a diluent and a mixture of organic salts of half ester-half acids having the general structure of STRUCTURE (1) at a total concentration of from 0.01-30 wt. % of the composition:

where:
n is from 0-2;
G is a glyceride residue comprising a mixture of:

each FA is a straight-chain fatty acyl residue having from 4 to 24 carbon atoms and from 0 to 3 double bonds in the carbon chain;
R 1 and R 2 are independently selected from hydrogen, straight-chain or branched alkyl or alkenyl groups having from 1-18 carbon atoms or where R 1 and R 2 together with the two carbons atoms to which they attach and the —(CH 2 ) n — group form a cyclic structure having at least 5 carbon atoms; and
A is a neutralizing group.

21. A method for forming a corrosion-inhibiting composition comprising:
reacting a triglyceride of the general structure:

with glycerin in the presence of a transesterification catalyst to form a glyceride mixture, where each FA is a straight-chain fatty acyl residue having from 4 to 24 carbon atoms and from 0 to 3 double bonds in the carbon chain;
reacting the glyceride mixture with a cyclic carboxylic acid anhydride;
with a neutralizing base, neutralizing the product of the reaction of the glyceride mixture with the cyclic carboxylic acid anhydride; and
combining the neutralized reaction product with a diluent to form the corrosion-inhibiting composition, wherein the neutralized reaction product is at a total concentration of from 0.01-30 wt. % of the composition.

22. The method of claim 21 , wherein the cyclic carboxylic acid anhydride has the structure general structure of STRUCTURE (3):

where R 1 and R 2 are independently selected from hydrogen, straight-chain or branc

Assignees

• Lubrizol Corp

Inventors

• Mcguiness Mark J

Classifications

• C07C69/40

  Succinic acid esters · CPC title

• C10M2207/401

  used as base material · CPC title

• C10M133/08

  containing hydroxy groups · CPC title

• C10M133/46

  Imidazoles · CPC title

• C10M129/74

  of polyhydroxy compounds · CPC title