Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus acids or salts thereof
Reexamination Certificate
2000-09-11
2002-06-11
Kumar, Shailendra (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus acids or salts thereof
C544S106000, C544S107000, C544S110000, C558S151000, C558S152000, C558S155000, C562S011000, C564S305000
Reexamination Certificate
active
06403826
ABSTRACT:
The present invention relates to coating compositions comprising an organic film-forming binder, preferably a coating material, and certain aminophosphonic acids or aminophosphorous acids and/or their zirconium, bismuth and calcium salts, and salts thereof with certain amines, as corrosion inhibitors, to the use thereof in coating compositions for protecting metallic surfaces, and to novel aminophosphonic acids and novel salts of aminophosphonic acids and of aminophosphorous acids.
The use of alkali metal, alkaline earth metal, transition metal and amine salts of carboxylic acids, and of transition metal complexes of ketocarboxylic acids, as corrosion inhibitors in aqueous systems is known and is described, for example, in U.S. Pat. No. 4,909,987, EP-A-0 412 933, EP-A-0 496 555, EP-A-0 554 023 or EP-A-0 619 290.
EP-A-0 437 722 discloses certain amine oxides of phosphonic acids as corrosion inhibitors. U.S. Pat. No. 4,000,012 describes an anticorrosion effect of iron phosphate or zinc phosphate coatings on steel, the action of which is markedly improved by treatment with a solution of an &agr;-aminophosphonic acid or water-soluble salts thereof. U.S. Pat. No. 4,076,501 refers to an anticorrosion effect of metals by means of diphosphonic acids. U.S. Pat. No. 4,917,737 describes a method of sealing off a phosphated metal substrate using certain alkylaminodiphosphonic acids. U.S. Pat. No. 3,925,245 (DE-A-2 231 206) refers to a corrosion-inhibiting composition for metal surfaces, comprising inorganic nitrites and aminoalkylphosphonic acids. U.S. Pat. No. 3,837,803 (DE-A-2 335 331) relates to a process of corrosion inhibition for metallic components which are in contact with aqueous systems, through the use of synergistic mixtures of water-soluble organophosphonic acids and their salts, a water-soluble orthophosphate, and calcium ions. U.S. Pat. No. 3,483,133 relates to the use of certain aminomethylphosphonic acids as corrosion inhibitors for metals in aqueous systems. GB-A-1 201 334 likewise discloses the use of certain phosphonic acids as corrosion inhibitors for metals in aqueous systems.
GB-A-2 121 419 discloses the use of certain phosphonic acids as corrosion inhibitors in coating materials.
One of the objects of the invention, then, was to provide—specifically for coating systems, especially those which are water-based—a coating composition which, firstly, inhibits or eliminates entirely the corrosion of metals, and, secondly, promotes good adhesion of the coating to the metal.
It has been found that certain aminophosphonic acids or aminophosphorous acids and/or their zirconium, bismuth and calcium salts, and also the salts thereof with certain amines, surprisingly suppress the oxidation of metals, and at the same time they greatly improve the adhesion of the coating to the metal. These acids and salts are for the most part novel, and are particularly suitable in the novel coating compositions both as corrosion inhibitors and as adhesion promoters.
The invention therefore relates to coating compositions comprising
a) an organic film-forming binder, and
b) as corrosion inhibitor &agr;) at least one compound of the formula I
in which
R
1
is hydroxyl-, carboxyl- or amino-substituted C
4
-C
12
alkyl; or R
1
and R
5
, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered heterocyclic ring which is unsubstituted or is substituted by C
1
-C
4
alkyl or is interrupted by oxygen, sulfur or
R
2
and R
3
independently of one another are hydrogen, C
1
-C
20
alkyl, C
5
-C
8
cycloalkyl, unsubstituted or C
1
-C
4
alkyl-substituted phenyl; or are benzyl,
R
4
is hydroxyl,
R
5
is
R
6
is C
1
-C
18
alkyl or C
7
-C
9
phenylalkyl, and
m is 0 or 1; or
&bgr;) at least one salt derived from i) a compound of the formula I′
in which
R′
1
is hydrogen, C
1
-C
25
alkyl, C
3
-C
25
alkyl interrupted by oxygen, sulfur or
hydroxyl-, carboxyl- or amino-substituted C
2
-C
25
alkyl; C
2
-C
24
alkenyl, C
4
-C
15
cycloalkyl, unsubstituted or C
1
-C
4
alkyl-substituted phenyl; C
7
-C
9
phenylalkyl or
or R′
1
and R′
5
, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered heterocyclic ring which is unsubstituted or is substituted by C
1
-C
4
alkyl or is interrupted by oxygen, sulfur or
R′
4
is hydrogen, hydroxyl or —OR
8
,
R′
5
is hydrogen, C
1
-C
25
alkyl, C
3
-C
25
alkyl interrupted by oxygen, sulfur or
C
2
-C
24
alkenyl, C
4
-C
15
cycloalkyl, unsubstituted or C
1
-C
4
alkyl-substituted phenyl; C
7
-C
9
-phenylalkyl or
R
7
is hydrogen or C
1
-C
6
alkyl,
R
8
is C
1
-C
6
alkyl, C
4
-C
15
cycloalkyl or unsubstituted or C
1
-C
4
alkyl-substituted phenyl; with the proviso that, if R′
1
or R′
5
is hydrogen, m is 0; and
ii) an amine of the formula II
in which
R
14
and R
15
independently of one another are hydrogen, C
1
-C
25
alkyl, hydroxyl-substituted C
2
-C
24
alkyl, C
3
-C
25
alkyl interrupted by oxygen or sulfur; C
7
-C
9
-phenylalkyl which is unsubstituted or is substituted on the phenyl ring by C
1
-C
4
alkyl; C
3
-C
24
alkenyl or
or R
14
and R
15
, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered heterocyclic ring which is unsubstituted or is substituted by C
1
-C
4
alkyl or is interrupted by oxygen, sulfur or
R
16
is C
1
-C
25
alkyl, C
2
-C
25
alkyl which is interrupted by oxygen or sulfur; hydroxyl, C
1
-C
18
alkoxy or C
2
-C
24
alkenyl,
R
17
is hydroxyl, C
1
-C
18
alkoxy, or C
2
-C
18
alkoxy which is interrupted by oxygen or sulfur; and, if b is 0, three radicals R
17
together are N(CH
2
CH
2
O—)
3
,
X is a direct bond, C
1
-C
18
alkylene, C
2
-C
20
alkylidene, C
7
-C
20
phenylalkylidene, C
5
-C
8
cycloalkylene, unsubstituted or C
1
-C
4
alkyl substituted phenylene or naphthylene;
or is C
4
-C
18
alkylene which is interrupted by oxygen, sulfur or
with the proviso that never two nitrogen atoms are attached to the same carbon atom,
a is 1 or 2,
b is 0, 1 or 2, and,
if a is 1,
R
18
is hydrogen, C
1
-C
25
alkyl, hydroxyl-substituted C
2
-C
24
alkyl, C
3
-C
25
alkyl which is interrupted by oxygen or sulfur; unsubstituted or C
1
-C
4
alkyl-substituted phenyl; C
7
-C
9
-phenylalkyl which is unsubstituted or is substituted on the phenyl ring by C
1
-C
4
alkyl;
C
3
-C
24
alkenyl,
if a is 2,
R
18
is
and with the proviso that, if in the compound of the formula I′ R′
1
is C
1
-C
12
alkyl,
or 2-hydroxyethyl, R′
5
is
R
2
and R
3
are hydrogen, R′
4
is hydroxyl and m is 0, and, if in the compound of the formula II a is 1 and X is a direct bond, then at least one of the radicals R
14
, R
15
and R
18
is other than hydrogen; or
iii) zirconium, bismuth or calcium.
Hydroxyl-, carboxyl- or amino-substituted C
2
-C
2
alkyl is a branched or unbranched radical which contains preferably 1 to 3, in particular 1 or 2, hydroxyl, carboxyl or amino groups, such as, for example, hydroxyethyl, carboxyethyl, aminoethyl, 3-hydroxypropyl, 3-carboxypropyl, 3-aminopropyl, 2-hydroxypropyl, 2-carboxypropyl, 2-aminopropyl, 4-hydroxybutyl, 4-carboxybutyl, 4-aminobutyl, 3-hydroxybutyl, 3-carboxybutyl, 3-aminobutyl, 2-hydroxybutyl, 2-carboxybutyl, 2-aminobutyl, 5-hydroxypentyl, 5-carboxypentyl, 5-aminopentyl, 4-hydroxypentyl, 4-carboxypentyl, 4-aminopentyl, 3-hydroxypentyl, 3-carboxypentyl, 3-aminopentyl, 2-hydroxypentyl, 2-carboxypentyl, 2-aminopentyl, 6-hydroxyhexyl, 6-carboxyhexyl, 6-aminohexyl, 5-hydroxyhexyl, 5-carboxyhexyl, 5-aminohexyl, 4-hydroxyhexyl, 4-carboxyhexyl, 4-aminohexyl, 3-hydroxyhexyl, 3-carboxyhexyl, 3-aminohexyl, 2-hydroxyhexyl, 2-carboxyhexyl, 2-aminohexyl, 7-hydroxyheptyl, 7-carboxyheptyl, 7-aminoheptyl, 6-hydroxyheptyl, 6-carboxyheptyl, 6-aminoheptyl, 5-hydroxyheptyl, 5-carboxyheptyl, 5-aminoheptyl, 4-hydroxyheptyl, 4-carboxyheptyl, 4-aminoheptyl, 3-hydroxyheptyl, 3-carboxyheptyl, 3-aminoheptyl, 2-hydroxyheptyl, 2-carboxyheptyl, 2-aminoheptyl, 8-hydroxyoctyl, 8-carboxyoctyl, 8-aminooctyl, 7-hydroxyoctyl, 7-carboxyoctyl, 7-aminooctyl, 6-hy
Braig Adalbert
Frey Markus
Kramer Andreas
Wolf Jean-Pierre
Ciba Specialty Chemicals Corporation
Kumar Shailendra
Mansfield Kevin T.
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