Functional organophosphonic acid esters as preservative adhesion promoting agents and coating for metals

• US 4,048,374 A
• Filed: 06/26/1975
• Issued: 09/13/1977
• Est. Priority Date: 09/01/1973
• Status: Expired due to Term

• Current Assignee: Dynamit Nobel AG
• Original Assignee: Dynamit Nobel AG
• Inventors: Seiler, Claus-Dietrich, Kotzsch, Hans-Joachim, Vahlensick, Hans-Joachim
• Primary Examiner(s): Hoffman, James R.
• Application Number:
  US05/590,642
• Time in Patent Office: 810 Days
• Field of Search: 427/388 R, 427/409, 427/410, 427/384, 427/386, 427/388 D, 427/413, 427/417, 106/14, 428/457, 148/6.5 R
• US Class Current: 428/457
• CPC Class Codes: B05D 7/14 to metal, e.g. car bodies involving a chemical reaction between the metal and the coating C23
• CPC Class Codes: C07F 9/40 Esters thereof
• CPC Class Codes: C09D 5/08 Anti-corrosive paints
• CPC Class Codes: C23F 11/1676 Phosphonic acids
• CPC Class Codes: Y10T 428/31678 Of metal

Abstract

A method for protecting the surface of a metal surface which comprises applying to said surface an organophosphorus compound of the formula ##STR1## wherein A IS 0 OR 1

R is a branched or unbranched chained bivalent alkylene radical of 1 to 12 carbon atoms which is substituted or unsubstituted and can contain in the chain structure --O--, --S--, ##STR2## R'"'"' is a branched or unbranched alkyl radical of 1 to 12 carbon atoms which can be halogen substituted and can contain in the chain structure ##STR3## X is an epoxy ring, halogen, alkylene, carboxylic acid ester residue, amino, isocyanato, isothiocyanato, urea, thiourea, urethano, alkyl substituted thio radical or the radical or a heterocyclic ring containing O, S, or N in the ring structure; a new organophosphorus compounds having the formula set forth above and more particularly defined by specific chemical structures.

Claims

1. A method of protecting the surface of a metal which consists essentially of applying to said metal surface an organophosphorus compound of the formula ##STR13## wherein a = 0 or 1

R is a branched or unbranched chain bivalent alkylene radical of 1 to 12 carbon atoms which is substituted or unsubstituted and can contain in the chain structures ##STR14## R'"'"' is a branched or unbranched chain alkyl radical of 1 to 12 carbon atoms which can be halogen substituted and which can contain in the chain structure ##STR15## X is an epoxy ring, halogen, alkenyl, carboxylic acid ester residue, amino, isocyanato, isothiocyanato, urea, thiourea, urethano, alkyl substituted thio radical or the radical of a heterocyclic ring containing O, S or N in the ring structure.

2. A method according to claim 1 wherein X is chlorine.

3. A method according to claim 1 wherein X is bromine.

4. A method according to claim 1 wherein X is alkenyl of 2 to 8 carbon atoms.

5. A method according to claim 1 wherein X is a carboxylic acid ester residue, the ester function of which is an alkyl group of 1 to 8 carbon atoms, said residue having a saturated or unsaturated chain of between 2 and 8 carbon atoms attached to the carbonyl carbon atom.

6. A method according to claim 1 wherein X is an alkyl substituted thio radical wherein the alkyl group has between 1 and 8 carbon atoms.

7. A method according to claim 1 wherein X is a heterocyclic ring having between 3 and 7 members in the ring.

8. A method according to claim 1 wherein after said compound is applied to the metallic surface it is heated at a temperature of room temperature to 300°

C.

9. A method according to claim 8 wherein said compound is heated at a temperature above 100°

C.

10. A method according to claim 8 wherein said compound is applied to said surface while dissolved in a solvent.

11. A method according to claim 10 wherein said solvent is ethanol.

12. A method according to claim 8 wherein said compound is applied to said surface while maintained in a paint, lacquer, varnish, resin, plastic or rubber.

13. A method according to claim 12 wherein said compound is applied to said surface while maintained in an epoxy resin, polyester resin, phenolic resin, urea resin, vulcanizable polybutadiene resin, a natural olefinically unsaturated polymer, a synthetic unsaturated polymer or a drying oil derived from an unsaturated fatty acid.

14. A method according to claim 8 wherein between 0.05 and 200 grams of said compound are applied per square meter of surface area.

15. A method according to claim 1 wherein R'"'"' is a branched or unbranched chain alkyl radical of 1 to 5 carbon atoms.

16. A method according to claim 1 wherein said compound is applied to said surface and thereafter there is applied thereto a paint, lacquer, varnish, resin, plastic or rubber.

17. A method according to claim 1 wherein said compound is at least partially saponified.

18. A metal protected by a coating of an organophosphorus compound of the formula ##STR16## wherein a = 0 or 1

R is a branched or unbranched chain bivalent alkylene radical of 1 to 12 carbon atoms which is substituted or unsubstituted and can contain in the chain structures ##STR17## R'"'"' is a branched or unbranched chain alkyl radical of 1 to 12 carbon atoms which can be halogen substituted and which can contain in the chain structure ##STR18## X is an epoxy ring, halogen, alkenyl, carboxylic acid ester residue, amino, isocyanato, isothiocyanato, urea, thiourea, urethano, alkyl substituted thio radical or the radical of a heterocyclic ring containing O, S or N in the ring structure.

19. A coated surface according to claim 18 wherein X is chlorine.

20. A coated surface according to claim 18 wherein X is bromine.

21. A coated surface according to claim 18 wherein X is alkenyl of 2 to 8 carbon atoms.

22. A coated surface according to claim 18 wherein X is a carboxylic acid ester residue, the ester function of which is an alkyl group of 1 to 8 carbon atoms, said residue having a saturated or unsaturated chain of between 2 and 8 carbon atoms attached to the carbonyl carbon atoms.

23. A coated article according to claim 18 wherein X is an alkyl substituted thio radical wherein the alkyl group has between 1 and 8 carbon atoms.

24. A coated article according to claim 23 having thereon a paint, lacquer, varnish, resin, plastic or rubber.

25. A coated article according to claim 18 wherein X is a heterocyclic ring having between 3 and 7 members in the ring.

26. A coated surface according to claim 18 wherein, upon the organophosphonic acid ester there is present a protective coating of an organic substance.