Cotelomer compounds

• US 4,681,686 A
• Filed: 07/10/1985
• Issued: 07/21/1987
• Est. Priority Date: 01/13/1984
• Status: Expired due to Term

• Current Assignee: FMC Corporation
• Original Assignee: Ciba-Geigy Corporation 444 Saw Mill River Road Ardsley New York
• Inventors: Holt, Brian, Cook, Barry, Richardson, Norman
• Primary Examiner(s): Wax, Robert A.
• Application Number:
  US06/753,510
• Time in Patent Office: 741 Days
• Field of Search: 210/699, 210/701, 252/175, 252/180, 252/181, 526/233, 526/240, 526/273, 526/277, 526/278
• US Class Current: 210/699
• CPC Class Codes: C02F 5/14 containing phosphorus
• CPC Class Codes: C08F 2/38 Polymerisation using regulators, e.g. chain terminating agents , e.g. telomerisation
• CPC Class Codes: C08F 220/04 Acids; Metal salts or ammonium salts thereof
• CPC Class Codes: C23F 11/173 Macromolecular compounds
• CPC Class Codes: C25D 11/246 for sealing layers

Abstract

New cotelomer compounds having the formula I ##STR1## and salts thereof wherein A is a random polymeric residue comprising at least one unit of formula II ##STR2## and at least one unit of formula III, different from a unit of formula II, ##STR3## and B is hydrogen or a residue A; wherein m and n are integers such that the sum of m+n is an integer of from 3 to 100, the ratio of n:m being from 99 to 1:1 to 99, provided that the resulting telomers are water-soluble and wherein m and/or n in a residue A may be the same as or different from m and/or n in a residue B; R is hydrogen, methyl or ethyl;

R₁ is a residue -OX, wherein X is hydrogen, an alkali- or alkaline earth metal, ammonium or an amine residue;

R₂ is hydrogen, methyl or a residue --CO₂ R₅, wherein R₅ is hydrogen or a straight- or branched chain alkyl residue having 1 to 8 carbon atoms;

R₃ is hydrogen, a straight- or branched chain alkyl residue having 1 to 4 carbon atoms, hydroxymethyl or a residue --CO₂ R₆, wherein R₆ is hydrogen, a residue of formula ##STR4## a residue of formula --[CH₂ --CH(R₉)O]_z H, in which R₉ is hydrogen, methyl or phenyl and z is an integer from 1 to 20, or R₆ is a straight- or branched chain alkyl residue having 1 to 8 carbon atoms or by a group SO₃ M in which M is hydrogen or an alkali- or alkaline earth metal atom;

R₄ is a residue --CO₂ R₆ (wherein R₆ has its previous significance), a straight- or branched alkyl residue having 1 to 8 carbon atoms optionally substituted by one to three carboxylic acid groups, a phenyl residue, an acetyl residue, hydroxymethyl, an acetomethyl residue, --SO₃ M, --CH₂ SO₃ M or --PO₃ M₂, in which M is hydrogen or an alkali metal or alkaline earth metal atom, a residue --CONR₇ R₈, wherein R₇ and R₈ are the same or different and each is hydrogen, a straight- or branched chain alkyl residue having 1 to 8 carbon atoms, hydroxymethyl or a residue --CH(OH)CO₂ M, --C(CH₃)₂ CH₂ SO₃ M or --C(CH₃)₂ CH₂ PO₃ M₂, wherein M has its previous significance, or --N(R₁₀)COCH₃, in which R₁₀ is hydrogen or C₁ -C₄ straight or branched chain alkyl group.

Compounds I are useful as corrosion and/or scale inhibitors in aqueous systems, as agents for facilitating dispersion of particulate matter in aqueous systems and as sealing smut inhibitors in processes for sealing anodically produced oxide layers on aluminium surfaces.

Claims

1. A cotelomer compound having the formula ##STR13## and salts thereof wherein A is a random polymeric residue comprising at least one unit of formula II ##STR14## and at least one unit of formula III, different from a unit of formula II, ##STR15## and B is hydrogen or a residue A;

wherein m and n are integers such that the sum of m+n is an integer of from 3 to 100, the ratio of n;

m being from 99 to 1;

1 to 99, provided that the resulting telomers are water-soluble and wherein m, n or m and n in a residue A are the same or different from m, n or m and n in a residue B;

R is hydrogen, methyl or ethyl;

R₁ is a residue --OX, wherein X is hydrogen, an alkali metal, an alkaline earth metal, ammonium or an amine residue;

R₂ is hydrogen, methyl or a residue --COOR₅ wherein R₅ is hydrogen or a straight or branched chain alkyl having 1 to 8 carbon atoms;

R₃ is hydrogen, a straight or branched chain alkyl having 1 to 4 carbon atoms, hydroxymethyl or --COOR₆ wherein R₆ is hydrogen, a residue of the formula ##STR16## or a residue of the formula

space="preserve" listing-type="equation">--[CH.sub.2 --CH(R.sub.9)O].sub.z H

in which R₉ is hydrogen, methyl or phenyl and z is an integer from 1 to 20, or R₆ is a straight or branched chain alkyl having 1 to 8 carbon atoms or said alkyl substituted by --SO₃ M or by --COOM where M is hydrogen or an alkali metal or alkaline earth metal atom;

R₄ is --COOR₆ where R₆ is as defined above, or R₄ is a straight or branched alkyl having 1 to 8 carbon atoms or said alkyl substituted by one to three carboxylic acid groups;

or R₄ is phenyl or said phenyl substituted by --SO₃ M or by --PO₃ M₂ ;

or R₄ is acetoxy, hydroxymethyl, acetoxymethyl, --SO₃ M, --CH₂ SO₃ M, --PO₃ M₂ or --PO₃ M'"'"'₂ in which M is hydrogen or an alkali metal or alkaline earth metal atom and M'"'"' is M or alkyl of 1 to 4 carbon atoms;

or R₄ is a residue --CONR₇ R₈ wherein R₇ and R₈ are the same or different and each is hydrogen, straight or branched chain alkyl having 1 to 8 carbon atoms, hydroxymethyl, --CH(OH)COOM, --C(CH₃)₂ CH₂ SO₃ M, --C(CH₃)₂ CH₂ PO.sub. 3 M₂ or --N(R₁₀)COCH₃ in which R₁₀ is hydrogen or straight or branched chain alkyl of 1 to 4 carbon atoms,

with the proviso that, when R₂ and R₃ are each hydrogen, then R₄ is other than --COOR₆ in which R₆ is --CH₂ CH(R₉)OH where R₉ is hydrogen or methyl.

2. A compound of formula I according to claim 1, wherein R is hydrogen or methyl.

3. A compound of formula I according to claim 1, wherein B is a residue A as defined in claim 1.

4. A compound of formula I according to claim 1, wherein R₁ is a residue of formula --OX wherein X is as defined in claim 1.

5. A compound of formula I according to claim 4 wherein X is an alkali metal.

6. A compound of formula I according to claim 5 wherein the alkali metal is sodium.

7. A compound of formula I according to claim 1 wherein

B is a residue A,

R is hydrogen or methyl,

R₂ is hydrogen, methyl or --COOR₅ wherein R₅ is hydrogen or alkyl of 1 to 8 carbon atoms,

R₃ is hydrogen, methyl or --COOR₆ wherein R₆ is defined in claim 30, and

R₄ is --COOR₆, or R₄ is alkyl of 1 to 8 carbon atoms or said alkyl substituted by one to three carboxyl groups, or R₄ is phenyl, acetoxy, hydroxymethyl, acetoxymethyl, --SO₃ M, --PO₃ M₂ or --PO₃ M'"'"'₂ in which M is defined in claim 30 and M'"'"' is M or ethyl, or R₄ is --CONR₇ R₈ or --N(R₁₀)COCH₃ where R₇, R₈ and R₁₀ are defined in claim 30, and

the sum of m and n is from 3 to 32.

8. A compound of formula I according to claim 1 wherein

R is hydrogen,

R₂ is hydrogen, methyl or --COOR₅ where R₅ is methyl,

R₃ is hydrogen, methyl or carboxyl, and

R₄ is --COOR₆ where R₆ is hydrogen, methyl, 2-carboxyethyl, --CH₂ CH₂ CH₂ SO₃ K or --(CH₂ CH₂ O)_z H where z is 2, or

R₄ is --SO₃ Na, phenyl, hydroxymethyl, acetoxy, --PO(OC₂ H₅)₂, --CH₂ COOH or --CH(COOH)CH₂ COOH, or

R₄ is --CONH₂, --CONHCH₂ OH, --CONHCH(OH)COOH or --CONHC(CH₃)₂ CH₂ SO₃ H.

9. Process for the production of compounds of formula I according to claim 1 comprising reacting n moles of an acid of formula IV

10. Process according to claim 9 wherein R₁ is a residue --OX in which X is an alkali metal.

11. Process according to claim 10 wherein the alkali metal is sodium.

12. Method of treating a wholly or partly aqueous system, in contact with metal surfaces, in order to inhibit scale formation on the metal surfaces or to inhibit corrosion of the metal surfaces or to facilitate dispersion of particulate matter in the aqueous system or inhibit sealing smut deposition therefrom, comprising adding to the aqueous system a functionally-effective amount of a cotelomeric compound of formula I, as defined in claim 1, or a salt thereof.

13. Method according to claim 12, wherein the compound of formula I R is hydrogen or methyl.

14. Method according to claim 12, wherein the compound of formula I substituent B in the compound of formula I is a residue A as defined in claim 1.

15. Method according to claim 12 wherein the compound of formula I X is an alkali metal.

16. Method according to claim 15 wherein the alkali metal is sodium.

17. A method according to claim 12 wherein the compound of formula I

B is a residue A,

R is hydrogen or methyl,

R₂ is hydrogen, methyl or --COOR₅ wherein R₅ is hydrogen or alkyl of 1 to 8 carbon atoms,

R₃ is hydrogen, methyl or --COOR₆ wherein R₆ is hydrogen a residue of the formula ##STR19## or a residue of the formula

18. A method according to claim 12 wherein the compound of formula I

R is hydrogen,

R₂ is hydrogen, methyl or --COOR₅ where R₅ is methyl,

R₃ is hydrogen, methyl or carboxyl, and

R₄ is --COOR₆ where R₆ is hydrogen, methyl, 2-carboxyethyl, --CH₂ CH₂ CH₂ SO₃ K or --(CH₂ CH₂ O)_z H where z is 2, or

R₄ is --SO₃ Na, phenyl, hydroxymethyl, acetoxy, --PO(OC₂ H₅)₂, --CH₂ COOH or --CH(COOH)CH₂ COOH, or

R₄ is --CONH₂, --CONHCH₂ OH, --CONHCH(OH)COOH or --CONHC(CH₃)₂ CH₂ SO₃ H.

19. Method according to claim 12 wherein the aqueous system heated requires only corrosion-inhibiting treatment and a compound of formula I is added in amount of 0.1 to 50000 ppm.

20. Method according to claim 19, wherein a compound of formula I is added in amount of 1 to 500 ppm.

21. Method according to claim 12, wherein the aqueous system requires only anti-scale treatment and a compound of formula I is added in amount of 1 to 200 ppm.

22. Method according to claim 21, wherein a compound of formula I is added in amount of 1 to 30 ppm.

23. Method according to claim 12, wherein the aqueous system is a dilute dispersion and a compound of formula I is added, as dispersant, in amount of 1 to 200 ppm.

24. Method according to claim 23, wherein a compound of formula I is added in amount of 2 to 20 ppm.

25. Method according to claim 12, wherein the aqueous system is used to seal an anodically produced oxide layer on an aluminium surface and contains, as sealing smut inhibitor, 0.0005 to 0.5 g/l of a compound of formula I.