Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/39—Organic or inorganic per-compounds
  • C11D3/3945—Organic per-compounds
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/16—Organic compounds
  • C11D3/26—Organic compounds containing nitrogen
  • C11D3/32—Amides; Substituted amides
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
  • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
  • C11D17/0026—Structured liquid compositions, e.g. liquid crystalline phases or network containing non-Newtonian phase
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/39—Organic or inorganic per-compounds
  • C11D3/3947—Liquid compositions

Definitions

• the invention concerns a detergent composition which is a structured liquid comprising amido and imido peroxy acid bleaches.
• U.S. Patent 3,996,152 discloses a suspension of diperoxyacids through non-starch thickening agents such as Carbopol 940 in an aqueous media at low pH. Suitable actives were diperazelaic, diperbrassylic, dipersebacic and diperisophthalic acids.
• U.S. Patent 4,017,412 reports similar systems except that starch-based thickening agents were employed. From later investigations it became evident that the thickener types mentioned in the foregoing patents formed gel-like matrices which exhibited instability upon storage at elevated temperatures. At high concentrations they caused difficulties by uncontrollably raising viscosity to levels which were too high.
• U.S. Patent 4,642,198 (Humphreys et al) describes a variety of water-insoluble organic peroxyacids intended for suspension in an aqueous, low pH liquid. This patent discloses the use of surfactants, both anionic and nonionic, as suspending agents for the peroxyacid particles.
• the preferred peroxy material was 1,12-diperoxydodecanedioic acid (DPDA).
• EP 176 124 discloses a pourable bleach composition containing peroxycarboxylic acid in an aqueous suspension with 0.5 to 15% alkylbenzene sulphonic acid and low levels of sulphate salt.
• the present invention seeks to provide a fully formulated, aqueous-based heavy-duty liquid laundry detergent composition containing a stably suspended peroxy bleach which has a viscosity and bleaching and cleaning properties which are acceptable to the consumer.
• amido or imido peroxyacids can be successfully suspended, i.e. they do not decompose or undergo phase separation, for extended periods of time in an aqueous surfactant structured liquid.
• These peroxyacids are characterised by having a particular water solubility.
• the invention provides a cleaning composition comprising:
• pH-adjusting system assists in the stabilisation of the peroxyacids.
• the amido or imido organic peroxyacid has a water solubility of less than 5 x 10 ⁇ 5M.
• compositions of the invention find particular application as heavy duty laundry detergent liquids.
• Peroxyacids of the present invention are preferably selected from mono- or di- percarboxylic amido or imido acids.
• Mono-percarboxylic acids are of the general formula: wherein: R is selected from the group consisting of C1-C16 alkyl, C1-C16 cycloalkyl and C6-C12 aryl radicals; R1 is selected from the group consisting of hydrogen, C1-C16 alkyl, C1-C16 cycloalkyl and C6-C12 aryl radicals; R2 is selected from the group consisting of hydrogen, C1-C16 alkyl, C1-C16 cycloalkyl and C6-C12 aryl radicals and a carbonyl radical that can form a ring together with R when R3 is arylene; R3 is selected from the group consisting of C1-C16 alkylene, C5-C12 cycloalkylene and C6-C12 arylene radicals; n and m are integers
• Di-percarboxylic acids of the present invention may be of the general formula: wherein: R4 is selected from the group consisting of C1-C12 alkylene, C5-C12 cycloalkylene, C6-C12 arylene and radical combinations thereof; R5 is selected from the group consisting of hydrogen, C1-C16 alkyl and C6-C12 aryl radicals and a carbonyl radical that can form a ring together with R3; R6 is selected from the group consisting of hydrogen, C1-C16 alkyl and C6-C12 aryl radicals and a radical that can form a C3-C12 ring together with R3; R3 is selected from the group consisting of C1-C12 alkylene, C5-C12 cycloalkylene and C6-C12 arylene radicals; n' and n'' each are an integer chosen such that the sum thereof is 1; m' and m'' each are an integer chosen such that the sum thereof is 1; and M
• Particularly preferred materials are: N,N'-di(4-percarboxybenzoyl)-1,4-butanediamine; N,N'-di(4-percarboxybenzoyl)-1,2-phenylenediamine; N,N'-succinoyl-di(4-percarboxy)aniline; 4-percarboxybenzoyl aniline; N,N-phthaloyl-4-aminoperbenzoic acid; N,N'-di(4-percarboxybenzoyl)ethylenediamine; N,N'-di(4-percarboxyaniline) terephthalate; N,N,N',N'-1,2,4,5-tetracarboxybenzoyl-di(6-aminopercarboxycaproic acid); N,N'-di(4-percarboxybenzoyl)piperazine; N,N'-di(4-percarboxybenzoyl)-1,4-
• compositions of the invention is the monononylamide of peroxyadipic acid, the preparation of which is described in US patent 4686063
• Amounts of the amido or imido peroxyacids of the present invention may range from about 0.1 to about 40%, preferably from about 1 to about 10% by weight.
• the surface-active material may be naturally derived, such as soap or a synthetic material selected from anionic, nonionic, amphoteric, zwitterionic, cationic actives and mixtures thereof. Many suitable actives are commercially available and are fully described in the literature, for example in "Surface Active Agents and Detergents", Volumes I and II, by Schwartz, Perry and Berch.
• the total level of the surface-active material may range up to 70% by weight, preferably being from about 1% to about 50% by weight of the composition, most preferably 4 to 45%.
• Synthetic anionic surface-actives are usually water-soluble alkali metal salts of organic sulphates and sulphonates having alkyl radicals containing from about 8 to 22 carbon atoms, the term alkyl being used to include the alkyl portion of higher aryl radicals.
• suitable synthetic anionic detergent compounds are sodium and ammonium alkyl sulphates, especially those obtained by sulphating higher (C8-C18) alcohols produced for example from tallow or coconut oil; sodium and ammonium alkyl (C9-C20) benzene sulphonates, particularly sodium linear secondary alkyl (C10-C15) benzene sulfonates; sodium alkyl glyceryl ether sulphates, especially those ethers of the higher alcohols derived from tallow or coconut oil and synthetic alcohols derived from petroleum; sodium coconut oil fatty acid monoglyceride sulphates and sulphonates; sodium and ammonium salts of sulfuric acid esters of higher (C9-C18) fatty alcohol-alkylene oxide, particularly ethylene oxide reaction products; the reaction products of fatty acids such as coconut fatty acids esterified with isethionic acid and neutralized with sodium hydroxide; sodium and ammonium salts of fatty acid amides of methyl taurine
• nonionic surface-active compounds which may be used preferably together with the anionic surface active compounds, include in particular, the reaction products of alkylene oxides, usually ethylene oxide, with alkyl (C6-C22) phenols, generally 2-25 EO, i.e. 2-25 units of ethylene oxide per molecule; the condensation products of aliphatic (C8-C18) primary or secondary linear or branched alcohols with ethylene oxide, generally 2-30 EO, and products made by condensation of ethylene oxide with the reaction products of propylene oxide and ethylene diamine.
• alkylene oxides usually ethylene oxide
• alkyl (C6-C22) phenols generally 2-25 EO, i.e. 2-25 units of ethylene oxide per molecule
• condensation products of aliphatic (C8-C18) primary or secondary linear or branched alcohols with ethylene oxide generally 2-30 EO
• nonionic surface-actives include alkyl polyglucosides, esters of fatty acids and glucosides, long chain tertiary amine oxides, long chain tertiary phosphine oxides and dialkyl sulfoxides.
• Amounts of amphoteric or zwitterionic surface-active compounds can also be used in the compositions of the invention but this is not normally desired owing to their relatively high cost. If any amphoteric or zwitterionic detergent compounds are used, it is generally in small amounts in compositions based on the much more commonly used synthetic anionic and nonionic actives.
• the detergent compositions of the invention will normally also contain a detergency builder.
• Builder materials may be selected from (1) calcium sequestrant materials, (2) precipitating materials, (3) calcium ion-exchange materials and (4) mixtures thereof.
• Examples of calcium ion-exchange builder materials include the various types of water-insoluble crystalline or amorphous aluminosilicates, of which zeolites are the best known representatives, e.g. zeolite A, zeolite B (also known as Zeolite P), zeolite C, zeolite X, zeolite Y and also the zeolite P type as described in EP-A-0,384,070.
• zeolites are the best known representatives, e.g. zeolite A, zeolite B (also known as Zeolite P), zeolite C, zeolite X, zeolite Y and also the zeolite P type as described in EP-A-0,384,070.
• compositions of the invention may contain any one of the organic or inorganic builder materials, such as sodium or potassium tripolyphosphate, sodium or potassium pyrophosphate, sodium or potassium orthophosphate, sodium carbonate, the sodium salt of nitrilotriacetic acid, sodium citrate, carboxymethylmalonate, carboxymethyloxysuccinate, tartrate mono- and di-succinates, oxydisuccinate, crystalline or amorphous aluminosilicates and mixtures thereof.
• the organic or inorganic builder materials such as sodium or potassium tripolyphosphate, sodium or potassium pyrophosphate, sodium or potassium orthophosphate, sodium carbonate, the sodium salt of nitrilotriacetic acid, sodium citrate, carboxymethylmalonate, carboxymethyloxysuccinate, tartrate mono- and di-succinates, oxydisuccinate, crystalline or amorphous aluminosilicates and mixtures thereof.
• Polycarboxylic homo- and copolymers may also be included as builders and to function as powder structurants or processing aids. Particularly preferred are polyacrylic acid (available under the trademark Acrysol from the Rohm and Haas Company) and acrylic-maleic acid copolymers (available under the trademark Sokalan from the BASF Corporation) and alkali metal or other salts thereof.
• These builder materials may be present at a level of, for example, from 1 to 80% by weight, preferably from 3 to 30% by weight.
• the initial amount of peroxyacid should range in amount to yield anywhere from about 0.05 to about 250 ppm active oxygen per litre of water, preferably between about 1 to 50 ppm.
• Surfactant should be present in the wash water from about 0.05 to 3.0 grams per litre, preferably from 0.15 to 2.4 grams per litre. When present, the builder amount will range from about 0.1 to 3.0 grams per litre.
• organic peroxyacid bleaches are most stable at a low pH (3-6), whereas they are most effective as bleaches in moderately alkaline pH (7-9) solution.
• a pH jump system is employed to keep the pH of the product between 3 and 8.5 for peracid stability during storage, yet allow it to become moderately high (pH 7-9) in a wash water for bleaching and detergency efficacy.
• Most important is that there is obtained a pH jump of at least 0.5 units, preferably 1.0 units, optimally about 1.5 units.
• One pH jump system is borax 10H2O/polyol. Borate ion and certain cis-1,2-polyols complex when concentrated cause a reduction in pH.
• the complex Upon dilution, the complex dissociates, liberating free borate to raise the pH.
• polyols which exhibit this complexing mechanism with borate include catechol, galactitol, fructose, sorbitol and pinacol.
• sorbitol is the preferred polyol.
• ratios greater than about 1:1 of polyol to borax are usually required. Therefore, the preferred ratio of polyol to borax should range anywhere from about 1:1 to about 10:1, although the range may be as broad as 1:10 to 10:1.
• Borate compounds such as boric acid, boric oxide, borax with sodium ortho- or pyroborate may also be suitable as the borate component.
• the pH jump system is present in an amount from about 1 to about 40 by weight.
• An advantageous optional component in the compositions of the invention is a deflocculating polymer.
• Copolymers of hydrophilic and hydrophobic monomers usually are employed to form the deflocculating agent. Suitable polymers are obtained by copolymerizing maleic anhydride, acrylic or methacrylic acid or other hydrophilic monomers such as ethylene or styrene sulphonates and the like with similar monomers that have been functionalized with hydrophobic groups. These include the amides, esters, ethers of fatty alcohol or fatty alcohol ethoxylates. In addition to the fatty alcohols and ethoxylates, other hydrophobic groups, such as olefins or alkylaryl radicals, may be used.
• the copolymer have acceptable oxidation stability and that the copolymer have hydrophobic groups that interact with the lamellar droplets and hydrophilic groups of the structured liquid to prevent flocculation of these droplets and thereby, prevent physical instability and product separation.
• a copolymer of acrylic acid and lauryl methacrylate (molecular weight 3800) has been found to be effective at levels of 0.5 to 1.5%.
• the detergent compositions of the invention can contain any of the conventional additives in the amounts in which such materials are normally employed in detergent compositions.
• these additives include lather boosters such as alkanolamides, particularly the monoethanolamides derived from palmkernel fatty acids and coconut fatty acids, lather depressants such as alkyl phosphates and silicones, antiredeposition agents such as sodium carboxymethylcellulose and alkyl or substituted alkylcellulose ethers, other stabilizers such as ethylene diamine tetraacetic acid, fabric softening agents, inorganic salts such as sodium sulphate and, usually present in very small amounts, fluorescent whitening agents, perfumes, enzymes such as proteases, cellulases, lipases and amylases, germicides and colorants.
• lather boosters such as alkanolamides, particularly the monoethanolamides derived from palmkernel fatty acids and coconut fatty acids
• lather depressants such as alkyl phosphates
• compositions of the invention may be used to clean a wide of substrates, including hard surfaces, and especially fabrics.
• Monomethyl monopotassium terephthalate (175.8 g, 0.8056 mol) was suspended in toluene (2000 ml) in a 5 litre, 3-necked flask equipped with an overhead stirrer, a condenser, and an addition funnel.
• Thionyl chloride (58.76 ml, 0.8056 mol) was added dropwise to the rapidly stirred suspension and the mixture was heated at 67°C for three hours. After stirring overnight at room temperature, the reaction was filtered on a Buchner funnel through a bed of celite and the filtrate containing 4-carbomethoxybenzoyl chloride was retained. At this point the acid chloride can be isolated by addition of an equal volume of diethyl ether, filtration of the potassium chloride by-product and removal of the solvent in vacuo. For most procedures the toluene solution is used directly.
• PCBPIP N,N'-Di(4-Percarboxybenzoyl)piperazine
• N,N'-Di(4-percarboxybenzoyl) piperazine (4.07 g, 0.0099 mol) was dissolved in methanesulphonic acid (14 ml) and was treated with hydrogen peroxide (3.37 ml of a 70% solution, 0.0891 mol) at 0°C. The mixture was stirred at room temperature for 5 hours, then poured onto ice-water. The solids were collected on a Buchner funnel, washed with water until the pH was 5, then allowed to air dry overnight. Yield 3.91 g (95%) of a white powder; m.p. 268 (decomposed prior to melting (dec)). Iodometric tritration indicated 65% peracid. IR (nujol) 3100 (hydroxyl), 1760 (peracid carbonyl) cm ⁇ 1.
• PCBED N,N'-Di(4-Percarboxybenzoyl) ethylenediamine
• N,N'-Di(4-carbomethoxybenzoyl) ethylenediamine (5.0 g, 0.0129 mol) was dissolved in 30 ml of methanesulphonic acid and treated with hydrogen peroxide (4.4 ml of a 70% solution) at 0°C. The mixture was allowed to warm to room temperature and was stirred for 5 hours. It was poured onto ice and saturated ammonium sulphate, the solids were filtered and washed with water to a pH of 5. The activity was 78% by iodometric titration.
• N,N'-Di(4-carbomethoxybenzoyl)phenylenediamine (3.07 g, 0.0071 mol) was dissolved in methanesulfonic acid (40 ml) and treated with hydrogen peroxide (2.42 ml of a 70% solution, 0.0639 mol) at room temperature. After stirring at room temperature for 6 hours, the reaction was kept at 3°C for 12 hours. The mixture was poured onto saturated ammonium sulphate solution and ice and then isolated as before to yield 1.85 g (59%) of an orange powder; mp>315°c. Iodometric titration indicated 60% peracid. IR (nujol) 3230 (hydroxyl), 1755 (peracid carbonyl) cm ⁇ 1.
• 4-carbomethoxybenzoyl chloride (9.057 g, 0.0456 mol) was dissolved in chloroform (180 ml) in a 500 ml 3-necked flask equipped with a mechanical stirrer and an addition funnel. To this solution was added trans-1,4-diaminocyclohexane (2.60 g, 0.0228 mol), triethylamine (7.5 ml, 0.0535 mol) and chloroform (80 ml) at 0°C over a period of 30 minutes. The reaction was stirred for 2.5 hours and the product filtered from the chloroform. The wet solid was washed with 10% HCl and saturated aqueous NaCl.
• N,N'-Di(4-percarboxybenzoyl)-1,4-diaminocyclohexane (1,63 g, 0.0037 mol) was dissolved in methanesulphonic acid (10 ml) and treated with hydrogen peroxide (1.26 ml of 70% solution, 0.0333 mol) at room temperature. After 7 hours, the reaction was worked-up with ice water and dried in a vacuum oven at 25°C to give 1.57 g (95%) of a white powder; m.p. >310°C.
• Adipic acid monoethyl ester (25.63 g, 0.147 mol) was combined with thionyl chloride (34.98 g, 0.293 mol) in a round-bottomed flask equipped with a condenser and heated at 37°C for 3 hours. The condenser was replaced by a modified still head and excess thionyl chloride removed at 5 mm Hg. The product (26.84 g, 95%) was distilled as a clear liquid (59°C/about 0.1 mm Hg). IR 3550, 3420, 2950, 2910, 2840, 1785, 1715, 1455, 1360, 1230, 1170, 1140, 1080, 1010, 940 cm ⁇ 1.
• Carboethoxyadipoyl chloride (13.74 g, 0.071 mol) in chloroform (40 ml) was added to 1,4-phenylenediamine (3.89 g, 0.036 mol) in chloroform (330 ml) and triethylamine (7.53 ml, 0.054 mol) at 4°C.
• the reaction medium was allowed to warm to room temperature over the course of 5 hours. Recrystallization from ethyl acetate gave 6.30 g (42%) of a white fluffy solid; m.p. 156-160°C.
• N,N'-Di(carboethoxyadipoyl)-1,4-phenylenediamine (6.00 g, 0.0143 mol) was dissolved in methanesulphonic acid (21 ml) and was treated with hydrogen peroxide (4.87 ml of a 70% solution, 0.1287 mol) at room temperature. The product was isolated from ice water after 2 hours to give 4.97 g (88%) of a pale orange powder; m.p. 210-212 (dec). Iodometric titration indicated 87% peracid.
• PCBBD N,N'-Di(4-Percarboxybenzoyl)-1,4-butanediamine
• N,N'-Di(4-carbomethoxybenzoyl)-1,4-butanediamine (3.00 g, 0.007 mol) dissolved in methanesulfonic acid (25 ml) was treated with hydrogen peroxide (2.50 ml of a 70% solution, 0.066 mol) according to the aforedescribed method. After 5 hours at room temperature and 16 hours at 3°C, the peracid was precipitated over ice water, washed with water and dried to give 1.8 g (60%) of a white powder; m.p. 180 (dec). Iodometric titration indicated 74% peracid, 5.7% a.o. (theory: 7.7% a.o.).
• N,N'-Di(4-carbomethoxybenzoyl)-1,2-phenylenediamine (2.75 g, 0.0064 mol) was dissolved in methanesulphonic acid (25 ml) and cooled to 0°C. Hydrogen peroxide (1.57 ml of a 90% solution, 0.058 mol) was added dropwise. After 16 hours at room temperature, the reaction was worked-up as described above.
• N,N'-succinoyl-di(4-carbomethoxy)aniline (5.02 g, 0.013 mol) was dissolved in methanesulfonic acid (30 ml) and cooled to 0°C. Hydrogen peroxide (4.43 ml of a 70% solution, 0.117 mol) was added dropwise. After 6 hours at room temperature, the product was worked-up as usual to give a light tan powder; m.p. 201°C. Iodometric tritration indicated 72% peracid, 6.0% a.o. (theory: 8.2% a.o.).
• N,N'-Di(carboethoxyadipoyl)ethylenediamine (0.023 g, 0.00055 mol) was dissolved in methanesulfonic acid (1.4 ml) and treated with hydrogen peroxide (0.19 ml of a 70% solution, 0.00495 mol) at room temperature and stirred for 18 hours.
• the product which was difficult to isolate from ice water, was a flaky material (0.0088 g, 46%) which turned black ⁇ 220°C but did not melt before 350°C. Iodometric titration indicated 55% peracid.
• BP-PABA N-Benzoyl-4-aminoperoxybenzoic acid
• N-Benzoyl-4-aminobenzoic acid (5.0 g, 0.0207 mol) was dissolved in 20 ml of methanesulfonic acid. The mixture was cooled to 0°C and concentrated hydrogen peroxide (2.40 ml of a 70% solution, 0.0634 mol) was added dropwise. The mixture was allowed to stir for 3 hours at room temperature after which time it was poured onto a large amount of ice water. The precipitate was filtered on a Buchner funnel and washed with water until the pH of the filtrate was 4.5.
• PCBA 4-Percarboxybenzoyl aniline
• 1,2,4,5-tetracarboxybenzene dianhydride (20 g, 0.0917 mol) and 6-aminocaproic acid (24.6 g, 0.188 mol) were suspended in 200 ml of DMF and heated to 120°C. The solids dissolved when heated. After 3 hours, the solution was cooled, poured onto ice-water and filtered.
• DIPAP N,N,N',N'-1,2,4,5-tetracarboxybenzoyl-di(6-aminopercarboxycaproic acid)
• the dimide dicarboxylic acid (7.0 g, 0.0224 mol) above was dissolved in 55 ml of methanesulphonic acid and treated with 70% hydrogen peroxide (5.0 ml, 0.134 mol). After a short time, the reaction mixture became very thick and it was necessary to use a mechanical stirrer. The mixture was poured onto ice-water after 5 hours at room temperature and isolated as described previously. The activity was 98%; IR (nujol) 3270, 1760, 1740, 1710, 1155, 1055 cm ⁇ 1.
• TPCAP N,N'-Terephthaloyl-di(6-aminoperoxycaproic acid)
• N,N'-Terephthaloyl-di(6-aminocaproic acid)* (5.01 g, 0.0127 mol) was dissolved in 30 ml of methanesulfonic acid and treated with hydrogen peroxide (4.33 ml of 70%, 0.114 mol) at 0°C. The mixture was stirred at room temperature for 5.5 hours then worked-up as usual. Yield 4.91 g (92%); activity 88% (6.7% a.o., theory 7.6%); IR (nujol) 330, 3200, 1760, 1740, 1630, 1545 cm ⁇ 1.
• N,N'-Di(4-carboxyaniline)terephthalate (4.98 g, 0.012 mol) was suspended in 60 ml of methanesulfonic acid and treated with hydrogen peroxide (4.09 ml of a 70% solution, 0.108 mol). The mixture was heated at 30°C for 4.5 hours, then isolated as usual. Activity 91%, 6.7% a.o. (theoretical 7.3% a.o.). IR (nujol) 3380, 3200, 1740, 1660, 1600 cm ⁇ 1.
• Phthalic anhydride (10.0 g, 0.0675 mol) and 4-aminobenzoic acid (9.35 g, 0.0682 mol) were dissolved in 100 ml of anhydrous DMF and heated to 120°C for 4.5 hours. The mixture was cooled, poured onto ice water and filtered.
• the formulation used for this study contained 35% surface-actives and had a pH of 4.5 which was obtained with a borax/sorbitol pH jump system.
• the peracid was dosed at 2,500 ppm.
• Table I contains the base formulation.
• the tested formulations (base including peracid) were stored at 40°C and aliquots were removed periodically and titrated for the percent of remaining peracid. Half-lives of the tested formulations are reported in Table II.
• a peroxide stability half-life at 40°C of at least 10 days, preferably at least 15 days, more preferably at least 30 days, and optimally beyond 50 days.
• a basic premise of this invention is that the solubility of a peracid affects its stability in a formulation. Consequently, the water solubility value of various peracids has been measured and these values correlated with peroxide stability.
• the solubility experiments were conducted by rapidly stirring 0.2 g of the finely ground peracid in 50 ml of Milli-Q water containing 0.01 gl ⁇ 1 of a phosphonic acid Dequest 2041.
• the solution was heated to 40°C for 15 minutes then equilibrated to 25.0°C( ⁇ 1°C) using a water circulating bath. After 2 hours, the stirring was stopped and the solids were allowed to settle.
• An aliquot was filtered using a polypropylene disposable syringe fitted with a Millex-HA 0.45 ⁇ m filter unit. The pH of the filtrate was between 4.5 and 5.0.
• the clear filtrate was treated with potassium hydrogen phthalate buffer and potassium iodide and the concentrate of triiodide determined spectrophotometrically according to the method of Davies (Davies, D.M.; Deary, M.E. Analyst ⁇ 1988 ⁇ , 113 , 1477-1479.) This procedure was repeated one hour later to be sure an equilibrium value had been obtained. The reproducibility of the method was found to be ⁇ 10%.
• Table III SOLUBILITY OF SELECTED PERACIDS IN WATER (pH 4.5 to 5.0) Concentration of a.o.

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• 1993
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