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US4067878A
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Stabilization of solutions of 3-isothiazolones
Assignee: Rohm and Haas Co
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Filing: 1976-03-05
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Granted: 1978-01-10
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Expires: 1996-03-05
Abstract
Abstract Solutions of 3-isothiazolones are stabilized against chemical decomposition of the isothiazolone by adding thereto a metal nitrate or a metal nitrite.
Inventors
- 👤 George A. Miller
- 👤 Ernest D. Weiler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 23:34
CPC Classifications
C; C07; C07D; C07D275/00; C07D275/02; C07D275/03
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
219 words
A method of stabilizing a solution containing a 3-isothiazolone complex of the formula ##STR3## wherein Y is a hydrogen atom, an alkyl group of 1 to 18 carbon atoms, an alkenyl or alkynyl group of 2 to 18 carbon atoms, a cycloalkyl group of 3 to 12 carbon atoms, having a 3 to 8 carbon atom ring, an aralkyl group of up to 10 carbon atoms, or an aryl group of up to 10 carbon atoms; R is a hydrogen atom, a halogen atom, or a (C 1 -C 4 )alkyl group; R' is a hydrogen atom, a halogen atom, or a (C 1 -C 4 )alkyl group; M is a cation of barium, cadmium, calcium, chromium, cobalt, copper, iron, lead, magnesium, manganese, mercury, nickel, silver, strontium, tin or zinc; X is a chloride, bromide iodide, sulfate, nitrate, nitrite, acetate, chlorate, perchlorate, bisulfate, bicarbonate, oxalate, maleate, p-toluenesulfonate, carbonate, or phosphate anion; a is the integer 1 or 2; and n is an integer which for the anion X satisfies the valence of the cation M; against decomposition of the complex, which comprises adding to the solution a stabilizing amount of a metal salt selected from the group consisting of nitrates and nitrites of sodium, potassium, calcium, magnesium, copper, iron, nickel, zinc, barium, manganese, silver, and cobalt, and mixtures thereof.
Claim 2
Independent Claim
219 words
A method of stabilizing a solution containing a 3-isothiazolone complex of the formula ##STR3## wherein Y is a hydrogen atom, an alkyl group of 1 to 18 carbon atoms, an alkenyl or alkynyl group of 2 to 18 carbon atoms, a cycloalkyl group of 3 to 12 carbon atoms, having a 3 to 8 carbon atom ring, an aralkyl group of up to 10 carbon atoms, or an aryl group of up to 10 carbon atoms; R is a hydrogen atom, a halogen atom, or a (C 1 -C 4 )alkyl group; R' is a hydrogen atom, a halogen atom, or a (C 1 -C 4 )alkyl group; M is a cation of barium, cadmium, calcium, chromium, cobalt, copper, iron, lead, magnesium, manganese, mercury, nickel, silver, strontium, tin or zinc; X is a chloride, bromide iodide, sulfate, nitrate, nitrite, acetate, chlorate, perchlorate, bisulfate, bicarbonate, oxalate, maleate, p-toluenesulfonate, carbonate, or phosphate anion; a is the integer 1 or 2; and n is an integer which for the anion X satisfies the valence of the cation M; against decomposition of the complex, which comprises adding to the solution a stabilizing amount of a metal salt selected from the group consisting of nitrates and nitrites of sodium, potassium, calcium, magnesium, copper, iron, nickel, zinc, barium, manganese, silver, and cobalt, and mixtures thereof.
Claim 3
Dependent Claim
16 words
The method of claim 1 wherein the solution is an aqueous or polar organic solvent solution.
Claim 4
Dependent Claim
25 words
The method of claim 2 wherein the metal salt is added in an amount of about 1 to about 30% by weight of the solution.
Claim 5
Dependent Claim
12 words
The method of claim 3 wherein the solution is an aqueous solution.
Claim 6
Dependent Claim
42 words
The method of claim 4 wherein Y is a hydrogen atom, an unsubstituted alkyl group of 1 to 18 carbon atoms, a (C 3 -C 8 ) cycloalkyl group, an aralkyl group of up to 8 carbon atoms, or a phenyl group.
Claim 7
Dependent Claim
41 words
The method of claim 5 wherein Y is a hydrogen atom, an unsubstituted (C 1 -C 8 ) alkyl group, a cyclohexyl group, or a benzyl, phenethyl or phenyl group optionally substituted with up to two methyl groups or chlorine atoms.
Claim 8
Dependent Claim
30 words
The method of claim 6 wherein the 3-isothiazolone metal salt complex is the calcium chloride complex of 5-chloro-2-methyl-3-isothiazolone or a mixture of the calcium chloride complexes of 5-chloro-2-methyl-3-isothiazolone and 2-methyl-3-isothiazolone.
Claim 9
Dependent Claim
12 words
The method of claim 7 wherein the metal salt is calcium nitrate.
Claim 10
Dependent Claim
12 words
The method of claim 7 wherein the metal salt is magnesium nitrate.
Claim 11
Dependent Claim
30 words
The method of claim 6 wherein the 3-isothiazolone metal salt complex is the magnesium chloride complex of 5-chloro-2-methyl-3-isothiazolone or a mixture of the magnesium chloride complexes of 5-chloro-2-methyl-3-isothiazolone and 2-methyl-3-isothiazolone.
Claim 12
Dependent Claim
12 words
The method of claim 10 wherein the metal salt is magnesium nitrate.
Claim 13
Dependent Claim
12 words
The method of claim 2 wherein the solution is an alcoholic solution.
Claim 14
Dependent Claim
11 words
The method of claim 12 wherein the alcohol is propylene glycol.
Claim 15
Dependent Claim
206 words
A stabilized solution which comprises a solvent, a 3-isothiazolone complex of the formula ##STR4##wherein p1 Y is a hydrogen atom, an alkyl group of 1 to 18 carbon atoms, an alkenyl or alkynyl group of 2 to 18 carbon atoms, a cycloalkyl group of 3 to 12 carbon atoms, having a 3 to 8 carbon atoms ring, an aralkyl group of up to 10 carbon atoms, or an aryl group of up to 10 carbon atoms; R is a hydrogen atom, a halogen atom, or a (C 1 -C 4 ) alkyl group; R' is a hydrogen atom, a halogen atom, or a (C 1 -C 4 )alkyl group; M is a cation of barium, cadmium, calcium, chromium, cobalt, copper, iron, lead, magnesium, manganese, mercury, nickel, silver, strontium, tin or zinc; X is a chloride, bromide, iodide, sulfate, nitrate, nitrite, acetate, chlorate, perchlorate, bisulfate, bicarbonate, oxalate, maleate, p-toluenesulfonate, carbonate, or phosphate anion; a is the integer 1 or 2; and n is an integer which for the anion X satisfies the valence of the cation M; and a metal salt selected from the group consisting of nitrates and nitrites of sodium, potassium, calcium, magnesium, copper, iron, nickel, zinc, barium, manganese, silver, and cobalt, and mixtures thereof.
Claim 16
Dependent Claim
206 words
A stabilized solution which comprises a solvent, a 3-isothiazolone complex of the formula ##STR4##wherein p1 Y is a hydrogen atom, an alkyl group of 1 to 18 carbon atoms, an alkenyl or alkynyl group of 2 to 18 carbon atoms, a cycloalkyl group of 3 to 12 carbon atoms, having a 3 to 8 carbon atoms ring, an aralkyl group of up to 10 carbon atoms, or an aryl group of up to 10 carbon atoms; R is a hydrogen atom, a halogen atom, or a (C 1 -C 4 ) alkyl group; R' is a hydrogen atom, a halogen atom, or a (C 1 -C 4 )alkyl group; M is a cation of barium, cadmium, calcium, chromium, cobalt, copper, iron, lead, magnesium, manganese, mercury, nickel, silver, strontium, tin or zinc; X is a chloride, bromide, iodide, sulfate, nitrate, nitrite, acetate, chlorate, perchlorate, bisulfate, bicarbonate, oxalate, maleate, p-toluenesulfonate, carbonate, or phosphate anion; a is the integer 1 or 2; and n is an integer which for the anion X satisfies the valence of the cation M; and a metal salt selected from the group consisting of nitrates and nitrites of sodium, potassium, calcium, magnesium, copper, iron, nickel, zinc, barium, manganese, silver, and cobalt, and mixtures thereof.
Claim 17
Dependent Claim
10 words
The solution of claim 14 wherein the solvent is water.
Claim 18
Dependent Claim
15 words
The solution of claim 15 wherein the metal salt is calcium nitrate or magnesium nitrate.
References Cited (Backward Citations)
US3870795A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1981-01-09 | 1981-07-11 | 1982-01-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-09 | 1985-07-11 | 1986-01-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-09 | 1989-07-11 | 1990-01-10 | $7700.00 | Window Closed / Lapsed |