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Thio(cyclo)alkanepolycarboxylic acids containing heterocyclic substituents

Assignee: HALOX A DIVISION OF HAMMOND GROUP Inc
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Filing: 1990-10-10
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Granted: 1992-10-06
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Expires: 2010-10-10
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Abstract

Abstract Compounds of the formula I ##STR1## in which X is --S--, --O-- or --NH--, R is H or a monovalent substituent, n is 0 or 1 and R 1 , R 2 , R 3 and R 4 are H, alkyl, alkyl which is substituted by OH, halogen, COOH or alkoxy, unsubstituted or substituted aryl or aralkyl, or carboxyl, or R 1 and R 2 or R 1 and R 3 together are alkylene or R 1 and R 2 are a direct bond, at least two of the groups R 1 , R 2 , R 3 and R 4 being carboxyl or carboxyalkyl groups, and base addition salts thereof are effective corrosion inhibitors. The preparation of these novel polycarboxylic acids can be effected by various processes.

Inventors

  • 👤 Robert L. Bentley
  • 👤 Michael P. Savage
  • 👤 Kenneth W. Shelton

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 17:57
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/52; C07D263/54; C07D263/58; C07D235/00; C07D235/02; C07D235/04; C07D235/24; C07D235/28; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/70; C07D277/74; C23; C23F; C23F11/00; C23F11/08; C23F11/10; C23F11/16; C23F11/165

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 319 words
A process for inhibiting corrosion in an aqueous system in contact with a metal which formula I adding to said aqueous system an effective inhibiting amount of at least one compound of comprises ##STR21## in which each R independently of the others is H, C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 12 -alkylthio, C 1 -C 12 -alkylsulfonyl, phenyl, C 1 -C 16 -alkylphenyl, C 7 -C 16 -phenylalkyl, C 5 -C 8 -cycloalkyl, halogen, --NO 2 , --CN, --COOH, --COO(C 1 -C 4 -alkyl), --OH or a primary, secondary or tertiary amino or carbamoyl group having up to 20 C atoms, X is --O--, --S-- or --NH--, n is zero or 1, and, if n is 1, R 1 , R 2 , R 3 and R 4 independently of one another are H, C 1 -C 18 -alkyl, C 1 -C 4 -hydroxyalkyl, C 2 -C 12 -carboxyalkyl, C 1 -C 4 -halogenoalkyl, C 2 -C 10 -alkoxyalkyl, --COOH or aryl or aralkyl having 6-10 C atoms which is unsubstituted or substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, --NO 2 , --COOH, --OH or halogen, or R 1 and R 2 or R 1 and R 3 together are linear or branched C 3 -C 8 -alkylene which can be substituted by 1 or 2 carboxyl groups, or R 1 and R 2 together are a direct bond, and, if n is 0, R 2 and R 4 are carboxyl, subject to the proviso that the group ##STR22## contains at least two and not more than four carboxyl groups and that, in the event that X is NH and three of the radicals R are hydrogen, the group --C(R 1 )(R 3 )--CH(R 2 )(R 4 ) is not a 1,2 dicarboxyethyl group, and a base addition salt of this compound.
Claim 2
Dependent Claim 319 words
A process for inhibiting corrosion in an aqueous system in contact with a metal which formula I adding to said aqueous system an effective inhibiting amount of at least one compound of comprises ##STR21## in which each R independently of the others is H, C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 12 -alkylthio, C 1 -C 12 -alkylsulfonyl, phenyl, C 1 -C 16 -alkylphenyl, C 7 -C 16 -phenylalkyl, C 5 -C 8 -cycloalkyl, halogen, --NO 2 , --CN, --COOH, --COO(C 1 -C 4 -alkyl), --OH or a primary, secondary or tertiary amino or carbamoyl group having up to 20 C atoms, X is --O--, --S-- or --NH--, n is zero or 1, and, if n is 1, R 1 , R 2 , R 3 and R 4 independently of one another are H, C 1 -C 18 -alkyl, C 1 -C 4 -hydroxyalkyl, C 2 -C 12 -carboxyalkyl, C 1 -C 4 -halogenoalkyl, C 2 -C 10 -alkoxyalkyl, --COOH or aryl or aralkyl having 6-10 C atoms which is unsubstituted or substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, --NO 2 , --COOH, --OH or halogen, or R 1 and R 2 or R 1 and R 3 together are linear or branched C 3 -C 8 -alkylene which can be substituted by 1 or 2 carboxyl groups, or R 1 and R 2 together are a direct bond, and, if n is 0, R 2 and R 4 are carboxyl, subject to the proviso that the group ##STR22## contains at least two and not more than four carboxyl groups and that, in the event that X is NH and three of the radicals R are hydrogen, the group --C(R 1 )(R 3 )--CH(R 2 )(R 4 ) is not a 1,2 dicarboxyethyl group, and a base addition salt of this compound.
Claim 3
Dependent Claim 30 words
A process according to claim 1, wherein the compound of the formula I is added in an amount of 0.1 ppm to 5% by weight, based on the aqueous system.
Claim 4
Dependent Claim 43 words
A process according to claim 1, wherein the aqueous system is a cooling water system, an air-conditioning plant, a steam generating plant, a sea water evaporation plant, a heating or cooling water circulation system or an aqueous metal machining, anti-freeze or hydraulic fluid.
Claim 5
Dependent Claim 46 words
A process according to claim 1, wherein, in addition to the corrosion inhibitor of the formula I, one or more other corrosion inhibitors, dispersing agents, precipitants, oxygen acceptors, complexing agents, antifoaming agents, disinfectants, high-pressure additives or other known additives are also added to the aqueous system.
Claim 6
Dependent Claim 16 words
A process according to claim 1 where in the compound of formula I, X is --S--.
Claim 7
Dependent Claim 37 words
A process according to claim 1 where in the compound of formula I, one of R is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or amino and the other three Rs are hydrogen.
Claim 8
Dependent Claim 18 words
A process according to claim 6 where in the compound of formula I, all four Rs are hydrogen.
Claim 9
Dependent Claim 33 words
A process according to claim 1 where in the compound of formula I, two of the groups R 1 , R 2 , R 3 and R 4 are carboxyl or carboxyalkyl groups.
Claim 10
Dependent Claim 69 words
A process according to claim 1 where in the compound of formula I, n is 1 and R 1 , R 2 , R 3 and R 4 independently of one another are hydrogen, C 1 -C 12 -alkyl, C 1 -C 4 -hydroxyalkyl, C 2 -C 6 -carboxyalkyl, C 2 -C 10 -alkoxyalkyl, carboxyl, phenyl or benzyl, or R 1 and R 2 together are trimethylene or tetramethylene.
Claim 11
Dependent Claim 46 words
A process according to claim 9 where in the compound of formula I, n is 1 and R 1 , R 2 , R 3 and R 4 independently of one another are hydrogen, C 1 -C 4 -alkyl, carboxyl or C 2 -C 6 -carboxyalkyl.
Claim 12
Dependent Claim 38 words
A process according to claim 1 where the compound of formula I is a salt of an alkali metal, alkaline earth metal, metal of group IIB, IIIA or VIII of the periodic system, ammonia or an organic amine.
Claim 13
Dependent Claim 33 words
A process according to claim 11 where the compound of formula I is a sodium, potassium, ammonium, calcium, magnesium, zinc or aluminum salt or a salt of a primary, secondary or tertiary amine.
Claim 14
Dependent Claim 14 words
A process according to claim 1 wherein the compound of formula I is ##STR23##
Claim 15
Dependent Claim 37 words
A composition which comprises (a) an aqueous system, and (b) 0.1 ppm to 5% weight, based on the aqueous system, of at least one compound of formula I according to claim 1, acting as a corrosion inhibitor.

References Cited (Backward Citations)

US4612378A Cited
US4612049A Cited
US4652653A Cited
US4696763A Cited
US4719036A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1995-10-06 1996-04-06 1996-10-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1999-10-06 2000-04-06 2000-10-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2003-10-06 2004-04-06 2004-10-06 $7700.00 Window Closed / Lapsed

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