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US 12,492,352 B2Granted
Macromolecular corrosion (MCIN) inhibitors: structures, methods of making and using the same
AssigneePolnox Corporation
InventorsAshok L. Cholli, Murat Tonga
Life of this patent
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Abstract
Disclosed are multifunctional compounds represented by structural formula (I): methods of producing compounds represented by structural formula (I) and their use in inhibiting corrosion in corrodible material.
Claims9
A method of producing a compound having Structural Formula I:
- wherein
- X is
- each R1 is H, independently an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C10 alkyl group, a tertiary carbon group, a methyl group, a methoxy group, an optionally substituted aryl group, an optionally substituted alkoxy group, an optionally substituted carbonyl group, an optionally substituted alkoxycarbonyl group, —CH(R′″) (R′″COOH) wherein each R′″ independently C1-C10 linear or branched alkyl chain, or an optionally substituted carbocyclic or heterocyclic non-aromatic ring;
- i=0, 1, 2, 3;
- j=0 or 1;
- n is an integer from 1 to 1000 or 1 to 100, 1 to 50 or 1 to 25, 1 to 15, or 1 to 10,
- when n=1, then j=0;
- when n>1 then j=1;
- each R2 and R3 is independently H, a C1-C8 linear or branched or cyclic alkyl chain, an optionally substituted C1-C20 alkyl group, an optionally substituted C1-C10 alkyl group, a tertiary carbon group, a methyl group, a methoxy group, an optionally substituted aryl group, an optionally substituted alkoxy group, an optionally substituted carbonyl group, an optionally substituted alkoxycarbonyl group, or —CH(R′″)(R′″COOH)
- R is a C1-C24 linear or branched alkyl chain, alkenyl chain, or an isomerized structure (A) or (B):
- wherein Ra is a C1-C24 alkenyl linear or branched chain,
- the method comprising the steps of:
- (a) reacting X in a solvent with an aldehyde selected from the group of formaldehyde, acetaldehyde, valeraldehyde, butyraldehyde, isovaleraldehyde, 2-methyl butanal, benzaldehyde, cyclohexanecarbaldehyde, 3-methylcyclohexanecarbaldehyde, glyceraldehyde, and glucose aldehyde;
- (b) reacting the product of (a) with an alkyl acyl chloride, an oleoyl chloride, or alkenyl succinic anhydride selected from the group of octenyl succinic anhydride (OSA), dodecenyl succinic anhydride (DDSA);
- octadecenyl succinic anhydride (ODSA);
- polyisobutylene succinic anhydride (PIBSA) having a molecular weight from 300 to 1500;
- (c) reacting the product of (b) with maleic anhydride if the reactant used in (b) is an oleoyl chloride;
- and
- (d) reacting the succinic anhydride group of product in (c) with a C1-C24 linear or branched or cyclic alcohol.
16 more elements
A method of forming a compound represented by
- wherein,
- R is a C1-C24 linear or branched alkyl chain, or an alkenyl chain represented by
- wherein Rd is a linear or branched C1-C24 alkyl chain;
- or
- a structure (A) or (B)
- wherein Ra is a C1-C24 linear or branched alkenyl chain, an alkenyl chain portion of OSA, octenyl succinic anhydride;
- DDSA, dodecenyl succinic anhydride;
- ODSA, octadecenyl succinic anhydride;
- PIBSA, polyisobutylene succinic anhydride having a molecular weight range between 300 and 1500, and
- R1 is selected from the group consisting of
- n is an integer from 1 to 10,
- the method comprising the steps of:
- (a) reacting in a solvent at reflux a phenol having the following formula:
- wherein R1 is selected from the group consisting of
- or an alkyl acid chain represented by (a) or (b)
- with
- formaldehyde;
- (b) reacting the product in (a) with an oleoyl chloride or alkyl acyl chloride at ice temperature to room temperature for 1 hour to 24 hours, or an alkenyl succinic anhydride is selected from the group of OSA, octenyl succinic anhydride;
- DDSA, dodecenyl succinic anhydride;
- ODSA, octadecenyl succinic anhydride;
- PIBSA, polyisobutylene succinic anhydride having a molecular weight of 300-1500 at 80° C. to 150° C. for 1 to 24 hours,
- (c) reacting the product in (b) with maleic anhydride at 170° C.-210° C. for 1 hour to 24 hours if the reactant used in (b) is an oleoyl chloride;
- and
- (d) reacting the succinic anhydride group of the product of (c) with a C1-C24 linear or branched or cyclic alcohol at 80° C. to 150° C.
21 more elements
A method of making a compound having the structure
- wherein [X] is
- R is an alkenyl chain represented by
- wherein Rd independently is a linear or branched C1-C24 alkyl chain, the method comprising:
- a) reacting an oleic acid with a C1-C24 linear or branched or cyclic alcohol,
- b) reacting the product of (a) with a maleic anhydride at 170° C.-210° C. for 1 hour to 24 hours, and
- c) reacting a succinic anhydride group of the product of (b) with an X—OH selected from a group of a substituted phenol, ethylene glycol, hexanediol, neopentyl glycol, diethanolamine, trimethylolpropane, glycerol, triethanolamine, pentaerythritol, di-pentaerythritol at 80° C. to 150° C.
3 more elements
Dependencies are inferred from the claim text.