# US 5,347,008 A · Thio(cyclo) alkanepolycarboxylic acids containing heterocyclic substituents

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- Number: US 5,347,008 A
- Document ID: US5347008A
- Status: Granted
- Kind: A
- Application number: 07/975,153
- Filed: 1992-11-12
- Granted: 1994-09-13
- Earliest claimed: 1983-05-14
- Assignees: Ciba-Geigy Corporation
- Inventors: Robert L. Bentley; Michael P. Savage; Kenneth W. Shelton
- Web page: https://patentgrep.com/patent/US5347008A

## CPC

- C07D 263/58: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D 235/28: Sulfur atoms
- C07D 277/74: Sulfur atoms substituted by carbon atoms
- C23F 11/16: Sulfur-containing compounds
- C23F 11/165: {Heterocyclic compounds containing sulfur as hetero atom}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C23F: NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE (working metal by laser beams B23K26/00; desurfacing by applying flames B23K7/00; working of metal by electro-erosion B23H; producing decorative effects by removing surface material, e.g. by engraving, by etching, B44C1/22; electrolytic etching or polishing C25F); INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25

## Abstract

Compounds of the formula ##STR1## in which X is --S--, --O-- or --NH--, R is H or a monovalent substituent, n is 0 or 1 and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are H, alkyl, alkyl which is substituted by OH, halogen, COOH or alkoxy, unsubstituted or substituted aryl or aralkyl, or carboxyl, or R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3 together are alkylene or R.sup.1 and R.sup.2 are a direct bond, at least two of the groups R.sup.1, R.sup.2, R.sup.3 and R.sup.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.

## Claims

### Claim 1

An organic amine addition salt of a compound of formula I ##STR21## in which each of R independently of the others is H, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.1 -C.sub.12 -alkylthio, C.sub.1 --C.sub.12 -alkylsulfonyl, phenyl, C.sub.7 -C.sub.16 -alkylphenyl, C.sub.7 -C.sub.16 -phenylalkyl, C.sub.5 -C.sub.8 -cycloalkyl, halogen, --NO.sub.2, --CN, --COOH, --COO(C.sub.1 -C.sub.4 -alkyl), --OH or --NH.sub.2,
X is --S--,
n is zero or 1, and
when n is 1, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are H, C.sub.1 -C.sub.18 -alkyl, C.sub.1 -C.sub.4 -hydroxyalkyl, C.sub.2 -C.sub.12 -mono-, di- or tri-carboxyalkyl, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.2 -C.sub.10 -alkoxyalkyl, --COOH or aryl or aralkyl having 6 to 10 C atoms, or said aryl or said arallkyl substituted with C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, --NO.sub.2, --COOH, --OH or halogen, or
R.sup.1 and R.sup.2 together are linear or branched C.sub.3 -C.sub.8 -alkylene which is unsubstituted or substituted with 1 or 2 carboxyl groups, or
R.sup.1 and R.sup.2 together are a direct bond, and
when n is zero, R.sup.2 and R.sup.4 are carboxyl, subject to the proviso that the group ##STR22## contains at least two and not more than four carboxyl groups.

### Claim 2 (depends on 1)

An organic amine salt of a compound of formula I according to claim 1, in which one R is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or --NH.sub.2 and the other three Rs are hydrogen.

### Claim 3 (depends on 1)

An organic amine salt of a compound of formula I according to claim 1, in which all four Rs are hydrogen.

### Claim 4 (depends on 1)

An organic amine salt of a compound of formula I according to claim 1, in which two of the groups R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are carboxyl or carboxyalkyl groups.

### Claim 5 (depends on 1)

An organic amine salt of a compound of formula I according to claim 1, in which n is 1 and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are H, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.4 -hydroxyalky, C.sub.2 -C.sub.6 -carboxyalkyl, C.sub.2 -C.sub.10 -alkoxyalkyl, carboxyl, phenyl or benzyl, or R.sup.1 and R.sup.2 together are trimethylene or tetramethylene.

### Claim 6 (depends on 1)

An organic amine salt of a compound of formula I according to claim 1, in which n is 1 and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are H, C.sub.1 -C.sub.4 -alkyl, carboxyl or C.sub.2 -C.sub.6 -carboxyalkyl.

### Claim 7 (depends on 1)

An organic amine salt of a compound of formula I according to claim 1 which is ##STR23##

### Claim 8 (depends on 1)

An organic amine salt according to claim 1 wherein the organic amine is selected from the group consisting of methylmine, ethanolmine, diethylamine, dibutylamine, diethanolarnine, cyclohexylamine, trimethylamine, triisopropylarnine, trioctylamine and triethanolamine.