US4735740A
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Diperoxyacid precursors and method
Assignee: Clorox Co
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Filing: 1986-10-03
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Granted: 1988-04-05
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Expires: 2006-10-03
Abstract
Abstract Novel sulfonated phenyl esters of dicarboxylic acids are useful as diperoxyacid precursors in bleaching and laundering applications when combined with a source of peroxide. These diperoxyacid precursors can be produced by reacting a dicarboxylic acid, a phenol sulfonate, and a lower alkyl acid anhydride in an alkyl hydrocarbon solvent and removing a carboxylic acid byproduct through distillation. The diperoxyacid precursors have the structure: ##STR1## wherein n is an integer from about 4 to about 18 and M is an alkali metal, an alkaline earth metal, or ammonium. The diperoxyacid precursors have a high perhydrolysis profile coupled with a relatively low-to-moderate hydrolysis profile.
Inventors
- 👤 Alfred G. Zielske
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 04:52
CPC Classifications
C; C07; C07C; C07C309/00; C11; C11D; C11D3/00; C11D3/39; C11D3/3902; C11D3/3905; C11D3/3907; C11D3/3915
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
31 words
A diperoxyacid precursor compound having the structure ##STR15## wherein n is an integer from about 4 to about 18 and M is an alkali metal, an alkaline earth metal, or ammonium.
Claim 2
Dependent Claim
31 words
A diperoxyacid precursor compound having the structure ##STR15## wherein n is an integer from about 4 to about 18 and M is an alkali metal, an alkaline earth metal, or ammonium.
Claim 3
Dependent Claim
12 words
The compound as in claim 1 wherein n is 5 or 8.
Claim 4
Dependent Claim
10 words
The compound as in claim 2 wherein M is sodium.
Claim 5
Dependent Claim
85 words
A dry bleach composition comprising: a diperoxyacid precursor and a source of peroxide, the diperoxyacid precursor having the structure ##STR16## wherein n is an integer from about 4 to about 18 and M is an alkali metal, an alkaline earth metal, or ammonium, the source of peroxide in an amount effective to perhydrolyze at least most of the diperoxyacid precursor in the presence of an aqueous solution at a pH of at least about 9.0 and at a temperature of at least about 21° C.
Claim 6
Dependent Claim
85 words
A dry bleach composition comprising: a diperoxyacid precursor and a source of peroxide, the diperoxyacid precursor having the structure ##STR16## wherein n is an integer from about 4 to about 18 and M is an alkali metal, an alkaline earth metal, or ammonium, the source of peroxide in an amount effective to perhydrolyze at least most of the diperoxyacid precursor in the presence of an aqueous solution at a pH of at least about 9.0 and at a temperature of at least about 21° C.
Claim 7
Dependent Claim
31 words
The compound as in claim 4 wherein the source of peroxide includes sodium perborate monohydrate, sodium perborate tetrahydrate, sodium carbonate peroxyhydrate, sodium pyrophosphate peroxyhydrate, urea peroxyhydrate, sodium peroxide, and mixtures thereof.
Claim 8
Dependent Claim
23 words
The bleach composition as in claim 4 or 5 wherein a diperoxyacid forms from the diperoxyacid precursor as a result of perhydrolysis thereof.
Claim 9
Dependent Claim
111 words
A dry laundering composition comprising: an anionic, cationic, non-ionic, ampholytic or zwitterionic surfactant, or mixtures thereof; and a peroxygen bleach composition in an amount from about 1 wt. % to about 20 wt. % of the dry laundering composition, the peroxygen bleach composition including a diperoxyacid precursor and an alkaline peroxide, the diperoxyacid precursor having two ester moieties, the alkaline peroxide being in a mole ratio with respect to each ester moiety of the diperoxyacid precursor of at least about 2:1, the diperoxyacid precursor having the structure ##STR17## wherein n is an integer from about 4 to about 18 and M is an alkali metal, an alkaline earth metal, or ammonium.
Claim 10
Dependent Claim
111 words
A dry laundering composition comprising: an anionic, cationic, non-ionic, ampholytic or zwitterionic surfactant, or mixtures thereof; and a peroxygen bleach composition in an amount from about 1 wt. % to about 20 wt. % of the dry laundering composition, the peroxygen bleach composition including a diperoxyacid precursor and an alkaline peroxide, the diperoxyacid precursor having two ester moieties, the alkaline peroxide being in a mole ratio with respect to each ester moiety of the diperoxyacid precursor of at least about 2:1, the diperoxyacid precursor having the structure ##STR17## wherein n is an integer from about 4 to about 18 and M is an alkali metal, an alkaline earth metal, or ammonium.
Claim 11
Dependent Claim
36 words
The dry laundering composition as in claim 7 further comprising a laundry adjuvant, the laundry adjuvant including one or more of a detergent builder, a buffer, an enzyme, a wetting agent, a dye or a perfume.
Claim 12
Independent Claim
145 words
A method for synthesizing sulfonated phenyl esters comprising: providing an initial reaction mixture including a carboxylic acid or a dicarboxylic acid, a phenol sulfonate, a lower alkyl acid anhydride, and an alkyl hydrocarbon solvent, the phenol sulfonate and the lower alkyl acid anhydride each being in a molar ratio with respect to the dicarboxylic acid of at least about 2:1 or with respect to the carboxylic acid of at least about 1:1; heating the initial reaction mixture to a temperature between about 150° C. to about 300° C. and refluxing the heated reaction mixture for at least two hours to form an intermediate reaction mixture having a carboxylic acid by-product therein; and removing the carboxylic acid by-product as a distillate with the alkyl hydrocarbon solvent from the intermediate reaction mixture to form a subsequent mixture, said subsequent mixture including a sulfonated phenyl ester reaction product.
Claim 13
Independent Claim
145 words
A method for synthesizing sulfonated phenyl esters comprising: providing an initial reaction mixture including a carboxylic acid or a dicarboxylic acid, a phenol sulfonate, a lower alkyl acid anhydride, and an alkyl hydrocarbon solvent, the phenol sulfonate and the lower alkyl acid anhydride each being in a molar ratio with respect to the dicarboxylic acid of at least about 2:1 or with respect to the carboxylic acid of at least about 1:1; heating the initial reaction mixture to a temperature between about 150° C. to about 300° C. and refluxing the heated reaction mixture for at least two hours to form an intermediate reaction mixture having a carboxylic acid by-product therein; and removing the carboxylic acid by-product as a distillate with the alkyl hydrocarbon solvent from the intermediate reaction mixture to form a subsequent mixture, said subsequent mixture including a sulfonated phenyl ester reaction product.
Claim 14
Dependent Claim
46 words
The method as in claim 9 wherein the dicarboxylic acid has the structure ##STR18## wherein n is an integer from about 4 to about 18, and the heating of the initial reaction mixture is to a temperature of between about 150° C. to about 270° C.
Claim 15
Dependent Claim
29 words
The method as in claim 9 or 10 wherein the phenol sulfonate has the structure HOφSO.sub.3 M and M is an alkali metal, an alkaline earth metal, or ammonium.
Claim 16
Dependent Claim
22 words
The method as in claim 9 or 10 wherein the lower alkyl acid anhydride is acetic anhydride, propionic anhydride or butyric anhydride.
Claim 17
Dependent Claim
17 words
The method as in claim 9 or 10 wherein the lower alkyl acid anhydride is acetic anhydride.
Claim 18
Dependent Claim
28 words
The method as in claim 9 or 10 wherein the alkyl hydrocarbon solvent is hectane, octane, nonane, decane, undecane, dodecane, tridecane, mixtures thereof, or water insoluble isoparaffinic solvents.
Claim 19
Dependent Claim
22 words
The method as in claim 9 or 10 wherein the heating is at a temperature of about 200° to about 215° C.
Claim 20
Dependent Claim
22 words
The method as in claim 9 wherein the initial and the intermediate reaction mixture each has a solid and a liquid phase.
Claim 21
Dependent Claim
40 words
The method as in claim 10 wherein the sulfonated phenyl ester reaction product has the structure ##STR19## wherein n is an integer from about 4 to about 18 and M is an alkali metal, an alkaline earth metal, or ammonium.
Claim 22
Dependent Claim
19 words
The method as in claim 17 further comprising: isolating the reaction product following removal of substantially all acid by-product.
Claim 23
Dependent Claim
20 words
The method as in claim 18 wherein the reaction product is isolated by filtration and is thereafter purified by recrystallization.
Claim 24
Dependent Claim
37 words
The method as in claim 10 wherein the phenol sulfonate and the lower alkyl acid anhydride of the initial reaction are each in a molar ratio with respect to the dicarboxylic acid of greater than about 2:1.
Claim 25
Dependent Claim
17 words
The method as in claim 9 wherein the initial reaction mixture includes an acidic or basic catalyst.
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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) | 1991-04-05 | 1991-10-05 | 1992-04-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-04-05 | 1995-10-05 | 1996-04-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-04-05 | 1999-10-05 | 2000-04-05 | $7700.00 | Window Closed / Lapsed |