US3974090A
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Imino alkylimino phosphonates and method for preparing and using same
Assignee: Monsanto Co
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Filing: 1975-03-20
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Granted: 1976-08-10
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Expires: 1995-03-20
Abstract
Abstract Imino ethylimino methyl phosphonates of the formula RCH2CH2N(CH2PO3M2)2 ¦ N ANGLE CH2CH2N(CH2PO3M2)2 wherein R and M are hereinafter defined are prepared by reacting a phosphorus source (orthophosphorous acid or PCl3 and H2O), formaldehyde, and an amine of the formula R'N(CH2CH2NH2)2 wherein R' is hereinafter defined. The compounds are useful as sequestrants for metal ions, as precipitation or scale inhibitors and as corrosion inhibitors in aqueous media.
Inventors
- 👤 Robert S. Mitchell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 22:37
CPC Classifications
C; C23; C23F; C23F11/00; C23F11/08; C23F11/10; C23F11/167; C23F11/1676; C02; C02F; C02F5/00; C02F5/08; C02F5/10; C02F5/14; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3808; C07F9/3817
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
41 words
A nitrilo tris[ethylimino bis(methyl phosphonic acid)] compound having the general formula ##EQU6## wherein M is selected from the group consisting of hydrogen, alkali metal ions, ammonium ions, alkylammonium ions and mixtures of hydrogen and at least one other of said ions.
Claim 2
Dependent Claim
41 words
A nitrilo tris[ethylimino bis(methyl phosphonic acid)] compound having the general formula ##EQU6## wherein M is selected from the group consisting of hydrogen, alkali metal ions, ammonium ions, alkylammonium ions and mixtures of hydrogen and at least one other of said ions.
Claim 3
Dependent Claim
10 words
The compound of claim 1 wherein each M is sodium.
Claim 4
Dependent Claim
13 words
The compound of claim 1 wherein each M is an alkali metal ion.
Claim 5
Dependent Claim
12 words
The compound of claim 1 wherein each M is an ammonium ion.
Claim 6
Dependent Claim
12 words
The compound of claim 1 wherein each M is an alkylammonium ion.
Claim 7
Dependent Claim
5 words
Nitrilo tris[ethylimino bis(methyl phosphonic acid)].
Claim 8
Dependent Claim
5 words
Nitrilo tris[ethylimino bis(methyl phosphonic acid)].
Claim 9
Dependent Claim
5 words
Octasodium nitrilo tris[ethylimino bis(methyl phosphonate)].
Claim 10
Dependent Claim
5 words
Octasodium nitrilo tris[ethylimino bis(methyl phosphonate)].
Claim 11
Dependent Claim
5 words
Octaammonium nitrilo tris[ethylimino bis(methyl phosphonate)].
Claim 12
Dependent Claim
5 words
Octaammonium nitrilo tris[ethylimino bis(methyl phosphonate)].
Claim 13
Dependent Claim
88 words
A process for preparing a nitrilo tris[ethylimino bis(methyl phosphonic acid)] which comprises forming an aqueous mixture having a pH below about 4 and containing (1) a phosphorus source selected from the group consisting of (a) orthophosphorous acid and (b) a combination of PCl 3 and H 2 O, (2) formaldehyde and (3) nitrilotriethyleneamine in a molar ratio of (1) to (2) to (3) of about 6:6:1, and subjecting said mixture to temperatures above about 70°C. whereby said nitrilo tris[ethylimino bis(methyl phosphonic acid)] having multiple N--C--P linkages is formed.
Claim 14
Dependent Claim
88 words
A process for preparing a nitrilo tris[ethylimino bis(methyl phosphonic acid)] which comprises forming an aqueous mixture having a pH below about 4 and containing (1) a phosphorus source selected from the group consisting of (a) orthophosphorous acid and (b) a combination of PCl 3 and H 2 O, (2) formaldehyde and (3) nitrilotriethyleneamine in a molar ratio of (1) to (2) to (3) of about 6:6:1, and subjecting said mixture to temperatures above about 70°C. whereby said nitrilo tris[ethylimino bis(methyl phosphonic acid)] having multiple N--C--P linkages is formed.
Claim 15
Dependent Claim
38 words
The process of claim 9 wherein said mixture additionally contains about 0.01 weight percent to about 10 weight percent of halide ions in order to inhibit the oxidation of said orthophosphorous acid to orthophosphoric acid during said process.
Claim 16
Dependent Claim
107 words
A process for preparing nitrilo tris[ethylimino bis(methyl phosphonic acid)] which process comprises forming an aqueous mixture of nitrilotriethyleneamine and orthophosphorous acid in a molar ratio of said amine to said acid of about 1:6, and at least about 0.5 weight percent of halide ions, the pH of said mixture being below about 4, and blending into said mixture over a period of from about 10 minutes to about 3 hours while said mixture is at a temperature above about 85°C. at least under 6 molar equivalents of formaldehyde, based on the amount of said amine in said mixture, whereby said nitrilo tris[ethylimino bis(methyl phosphonic acid)] is produced.
Claim 17
Dependent Claim
107 words
A process for preparing nitrilo tris[ethylimino bis(methyl phosphonic acid)] which process comprises forming an aqueous mixture of nitrilotriethyleneamine and orthophosphorous acid in a molar ratio of said amine to said acid of about 1:6, and at least about 0.5 weight percent of halide ions, the pH of said mixture being below about 4, and blending into said mixture over a period of from about 10 minutes to about 3 hours while said mixture is at a temperature above about 85°C. at least under 6 molar equivalents of formaldehyde, based on the amount of said amine in said mixture, whereby said nitrilo tris[ethylimino bis(methyl phosphonic acid)] is produced.
Claim 18
Independent Claim
66 words
A method of inhibiting the precipitation of scale-forming salts in an aqueous system comprising adding to said system at least a precipitation inhibiting amount of a nitrilo tris[ethylimino bis(methyl phosphonic acid)] compound having the general formula ##EQU7## wherein M is selected from the group consisting of hydrogen, alkali metal ions, ammonium ions, alkylammonium ions and mixtures of hydrogen and at least one other of said ions.
Claim 19
Independent Claim
66 words
A method of inhibiting the precipitation of scale-forming salts in an aqueous system comprising adding to said system at least a precipitation inhibiting amount of a nitrilo tris[ethylimino bis(methyl phosphonic acid)] compound having the general formula ##EQU7## wherein M is selected from the group consisting of hydrogen, alkali metal ions, ammonium ions, alkylammonium ions and mixtures of hydrogen and at least one other of said ions.
Claim 20
Dependent Claim
18 words
The method of claim 12 wherein the scale-forming salt is an alkaline earth metal carbonate, sulfate or oxalate.
Claim 21
Dependent Claim
22 words
The method of claim 12 wherein the mole ratio of precipitation inhibitor to scale-forming salts is from about 1:1.5 to about 1:10,000.
Claim 22
Dependent Claim
25 words
The method of claim 14 wherein the precipitation inhibitor is present in the system at concentrations from about 0.1 to about 500 parts per million.
Claim 23
Dependent Claim
10 words
The method of claim 12 wherein each M is sodium.
Claim 24
Dependent Claim
13 words
The method of claim 12 wherein each M is an alkali metal ion.
Claim 25
Dependent Claim
12 words
The method of claim 12 wherein each M is an ammonium ion.
Claim 26
Dependent Claim
14 words
The method of claim 12 wherein said compound is nitrilo tris[ethylimino bis(methyl phosphonic acid)].
Claim 27
Independent Claim
68 words
A method of inhibiting the corrosion of metals in a water system comprising maintaining in the water of said system at least 3 parts per million of a nitrilo tris[ethylimino bis(methyl phosphonic acid)] compound having the general formula ##EQU8## wherein M is selected from the group consisting of hydrogen, alkali metal ions, ammonium ions, alkylammonium ions and mixtures of hydrogen and at least one other of said ions.
Claim 28
Independent Claim
68 words
A method of inhibiting the corrosion of metals in a water system comprising maintaining in the water of said system at least 3 parts per million of a nitrilo tris[ethylimino bis(methyl phosphonic acid)] compound having the general formula ##EQU8## wherein M is selected from the group consisting of hydrogen, alkali metal ions, ammonium ions, alkylammonium ions and mixtures of hydrogen and at least one other of said ions.
Claim 29
Dependent Claim
10 words
The method of claim 20 wherein each M is sodium.
Claim 30
Dependent Claim
13 words
The method of claim 20 wherein each M is an alkali metal ion.
Claim 31
Dependent Claim
12 words
The method of claim 20 wherein each M is an ammonium ion.
Claim 32
Dependent Claim
19 words
The method of claim 20 wherein the water of said system additionally contains a water-soluble compound of hexavalent chromium.
Claim 33
Dependent Claim
27 words
The method of claim 20 wherein the water of said system additionally contains a zinc compound soluble in water in the presence of said phosphonic acid compound.
Claim 34
Dependent Claim
41 words
The method of claim 20 wherein the water of said system additionally contains from about 0.05 to 5 ppm of a compound selected from the group consisting of 1,2,3-triazoles, thiols of thiazoles, thiols of oxazoles, thiols of imidazoles and mixtures thereof.
Claim 35
Dependent Claim
42 words
The method of claim 26 wherein the water of said system additionally contains a zinc compound soluble in water in the presence of said phosphonic acid compound, sufficient to supply to said water from about 2 to 100 ppm of zinc ions.
Claim 36
Dependent Claim
15 words
The method of claim 20 wherein the said compound is nitrilo tris[ethylimino bis(methyl phosphonic acid)].
Claim 37
Dependent Claim
92 words
A composition useful in inhibiting the corrosion of metals in a water system consisting essentially of from about 20 percent to about 90 percent by weight of a nitrilo tris[ethylimino bis(methyl phosphonic acid)] compound having the general formula ##EQU9## wherein M is selected from the group consisting of hydrogen, alkali metal ions, ammonium ions, alkylammonium ions and mixtures of hydrogen and at least one other of such ions, and from about 10 percent to about 80 percent of a zinc compound soluble in water in the presence of said phosphonic acid compound.
Claim 38
Dependent Claim
92 words
A composition useful in inhibiting the corrosion of metals in a water system consisting essentially of from about 20 percent to about 90 percent by weight of a nitrilo tris[ethylimino bis(methyl phosphonic acid)] compound having the general formula ##EQU9## wherein M is selected from the group consisting of hydrogen, alkali metal ions, ammonium ions, alkylammonium ions and mixtures of hydrogen and at least one other of such ions, and from about 10 percent to about 80 percent of a zinc compound soluble in water in the presence of said phosphonic acid compound.
Claim 39
Dependent Claim
124 words
A composition useful in inhibiting the corrosion of metals in a water system consisting essentially of (1) from about 20 percent to about 90 percent by weight of a nitrilo tris[ethylimino bis(methyl phosphonic acid)] compound having the general formula ##EQU10## wherein M is selected from the group consisting of hydrogen, alkali metal ions, ammonium ions and mixtures of hydrogen and at least one other of such ions, (2) from about 1 percent to about 10 percent by weight of a compound selected from the group consisting of 1,2,3-triazoles, thiols of thiazoles, thiols of oxazoles, thiols of imidazoles and mixtures thereof, and (3) up to about 79 percent by weight of a zinc compound soluble in water in the presence of said phosphonic acid compound.
Claim 40
Dependent Claim
124 words
A composition useful in inhibiting the corrosion of metals in a water system consisting essentially of (1) from about 20 percent to about 90 percent by weight of a nitrilo tris[ethylimino bis(methyl phosphonic acid)] compound having the general formula ##EQU10## wherein M is selected from the group consisting of hydrogen, alkali metal ions, ammonium ions and mixtures of hydrogen and at least one other of such ions, (2) from about 1 percent to about 10 percent by weight of a compound selected from the group consisting of 1,2,3-triazoles, thiols of thiazoles, thiols of oxazoles, thiols of imidazoles and mixtures thereof, and (3) up to about 79 percent by weight of a zinc compound soluble in water in the presence of said phosphonic acid compound.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-10 | 1980-02-09 | 1980-08-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-10 | 1984-02-09 | 1984-08-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-10 | 1988-02-09 | 1988-08-10 | $7700.00 | Window Closed / Lapsed |