US3816319A - Activation of peroxide washing and bleaching baths - Google Patents

Activation of peroxide washing and bleaching baths Download PDF

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Publication number
US3816319A
US3816319A US00146932A US14693271A US3816319A US 3816319 A US3816319 A US 3816319A US 00146932 A US00146932 A US 00146932A US 14693271 A US14693271 A US 14693271A US 3816319 A US3816319 A US 3816319A
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Prior art keywords
activator
washing
process according
soil
peroxide
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A Decamps
P Sarot
M Delattre
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Solvay SA
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Solvay SA
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    • 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
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing 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
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • 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
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • C11D3/38609—Protease or amylase in solid compositions only
    • 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
    • C11D3/395—Bleaching agents
    • C11D3/3951—Bleaching agents combined with specific additives

Definitions

  • the present invention relates to a process for the activation of peroxide compounds in aqueous solutions used for washing and bleaching, or for disinfection and decontamination, and also to solid compositions containing both a peroxide compound and the activator.
  • activators which even at low temperature permit washing and bleaching by means of liquids containing peroxide compounds while providing under these conditions good bleaching action and also satisfactory removal of stains.
  • activators mention may be made of the anhydrides of lower carboxylic acids, for example, acetic anhydride, substances containing one or more nitrogen atoms and at least two acyl groups bonded to the same nitrogen atom, particularly tetraacetylethylenediamine, and also acylated derivatives of 2,4,6-trihydroxy-l,3,5-triazine, preferably trisacetyl cyanurate.
  • the acetylated derivatives are the most effective, but their penetrating odor considerably limits their utility.
  • a peroxide compound in an aqueous medium is activated by the reaction product of a dioxime and an acetylation agent.
  • a solid composition useful for producing washing and bleaching baths is comprised of a solid peroxide compound and the reaction product of a dioxime with an acylation agent, which is effective as an activator for the peroxide compound.
  • FIG. 1 Each of the figures is a diagram wherein the time of soaking in hours (abscissa) has been plotted against the soil eliminated in percent (ordinate)
  • curves I and II concern soaking with a peroxide compound without an activator
  • curves III and IV concern soaking with a peroxide compound in the presence of 0.1 g. of an acylated dioxime
  • curves V and VI concern soaking in the presence of a peroxide compound and 0.5 g. of an acylated dioxime
  • curves VII and VIII concern soaking in the presence of a peroxide compound and 1.0 g. of an acylated dioxime.
  • the soil to be eliminated is tea (curves I, III, V and VII) and wine (curves II, IV and VI).
  • curve I concerns soaking with a peroxide compound without activation and curves II, III and IV concern soaking with a peroxide compound in the presence of diacetylated dimethylgloxime, diacetylated glyoxime and diacetylated methylethylglyoxime, respectively.
  • FIGS. 2 and 4 the diagrams concern tests of fabrics soiled with tea and in FIGS. 3 and 5, the diagrams concern tests of fabrics soiled with red wine.
  • acylation products of dioximes are acylation products, the acyl group of which contains from two to four carbon atoms, particularly acetylation products.
  • the compounds which can be used according to the invention are preferably the diacylated products of glyoxime and dialkylglyoximes in which the alkyl group contains from one to 12, preferably from one to four carbon atoms.
  • a particularly suitable compound is diacetylated dimethylglyoxime, the formula of which is probably one of the following:
  • This compound is'easily obtained by reacting acetic anhydride with dimethylglyoxime by the usual acetylation techniques. Its composition has been determined by elementary analysis and mass spectrometry. It is obtained in the form of a white powder of crystalline appearance an surprisingly is practically odorless, so that it has an undeniable advantage in the present application.
  • the use of the activators according to the invention makes it possible to obtain a sufficient degree of whiteness even at relatively low temperatures, so that in the process according to the invention the objects to be treated may be brought into contact with an aqueous solution containing the peroxide compound and the activator at temperatures between ambient temperature and C.
  • the process according to the invention is effective for bleaching paper pulp, textile materials, greases, oils, and all materials as well as all compounds usually bleached by means of peroxide solutions.
  • peroxide solutions aqueous solutions of peroxide compounds and activators may also be used for decontamination and disinfection.
  • the amount of peroxide compound varies wih the nature of the objects to be treated and the degree of whiteness which is desired; thus, for the decoloration of oils and greases it may be necessary to use larger amounts of peroxide compounds than for the bleaching of textile materials.
  • the diacylated dioximes used as activators in the present invention are effective even when they are present in the washing and bleaching baths at the rate of 0.05 mole per gram-atom of active oxygen; it is obvious that larger amounts may be used, but it scarcely appears advantageous to use more than one mole of activator per gram-atom of active oxygen.
  • the activators proposed may be added to the washing and bleaching baths at the time of use.
  • the activators proposed are in solid form, which is most frequently the case, they may also be mixed, preferably provided with a protective coating which is soluble in water or capable of dispersion therein, such as certain polyethylene glycols, polyvinyl alcohol, or other similar materials with the washing or bleaching powders containing peroxide compounds, so as to have available a pulverulent mixture ready for the preparation of the washing or bleaching bath by dissolving in water.
  • a protective coating which is soluble in water or capable of dispersion therein, such as certain polyethylene glycols, polyvinyl alcohol, or other similar materials with the washing or bleaching powders containing peroxide compounds, so as to have available a pulverulent mixture ready for the preparation of the washing or bleaching bath by dissolving in water.
  • Such ready-to-use mixtures may contain, in addition to the peroxide compound and the activator, anionic or non-ionic detergents having a washing action, alkaline substances regulating pH, and assisting the washing action, for example, carbonates, phosphates, pyrophosphates, tripolyphosphates, and silicates, antiredeposition agents such as carboxymethyl cellulose, optical bleaching products, proteolytic and/or amylolytic enzymes, stabilizers, anti-corrosive agents, etc.
  • anionic or non-ionic detergents having a washing action
  • alkaline substances regulating pH for example, carbonates, phosphates, pyrophosphates, tripolyphosphates, and silicates
  • antiredeposition agents such as carboxymethyl cellulose, optical bleaching products, proteolytic and/or amylolytic enzymes, stabilizers, anti-corrosive agents, etc.
  • EXAMPLE 1 the activities imparted by diacetylated dimethylglyoxime (DMGA) and by a known activator, triacetylcyanurate (TACA), to a perborate washing powder containing no activator and used for washing clothes under mild temperature conditions are compared.
  • DMGA diacetylated dimethylglyoxime
  • TACA triacetylcyanurate
  • the total duration of a washing cycle is therefore about 40 minutes.
  • the water feeding the machine has a hardness of 16 to 17 French hydrotimetric degrees; its temperature in the machine is 40C. i 1C.
  • the washing powder used at the rate of 2 g. per liter of 150 g. per cycle is a commercial product. Its composition, determined by analysis is as follows, in percent by weight:
  • sodium pyrophosphate 5 sodium sulphate tetrahydrated sodium perborate 20 water of crystallization, celluose derivatives, optical bleaching agent, etc. 10 100
  • the material to be washed is composed of two parts: a white load and various test pieces intended to evaluate washing effectiveness.
  • the load with a total weight of 3.5 kg., is composed of various pieces of about cm. in length and 50 cm. in width. These pieces are of mixed cloth based on cotton (65 percent) and polyester (35 percent). The whiteness of the cloth, measured by its reflectance in blue light, is 88.0 i 0.1 percent referred to magnesium oxide.
  • test pieces of about square cm. (12.5 cm. X 8 cm.) are sewn on the load. Fifteen types of test pieces were used at the rate of 10 test pieces per type. The fabrics to be tested were distributed in the following four groups;
  • test pieces intended to measure the detergent effectiveness of the washing product.
  • Second group fabrics covered with soil sensitive to the action of the enzymes used in washing powders.
  • the first group comprises three different cottons covered with pigmentary soil based on lampblack. These fabrics were prepared by the following specialized organizations: EMPA (Switzerland), TEST FABRICS (U.S.A.), and WFK KREFELD (West Germany).
  • the second group comprises EMPA l 12 and 1 l6 soiled cottons.
  • One of the cottons is impregnated with soil containing blood, milk, India ink, etc.; the other is soiled with cocoa.
  • the third group is composed of mixed cloth soiled with seven different stains; the staining was obtained by impregnating the fabric with a concentrated solution of the staining element, padding the impregnated cloth and drying in the open air, this staining cycle being repeated three times in succession.
  • Four stains were made with natural fruit jucies blackcurrant, bilberry, cherry, and grape and the other three are based on tea, coffee and red wine.
  • the effect of the washing treatment on the various test pieces is measured by the variation of their whiteness.
  • the latter is always determined on the hidden face of the test piece, that is to say the face in permanent contact with the load.
  • Whiteness is measured with the aid of an ELREPHO reflectometer (Zeiss) giving diffused lighting of the test piece and having an effective wavelength of 457 nanometers; the values obtained for refiectances are given in percent, referred to magnesium oxide.
  • perborate powder without activation, perborate powder activated by trisacetylcyanurate lsmperfllure 1C. 40 mlnutes 15 water used, hardness French degrees 16-17 perborate powder activated by discetylated dimethylvqlume cm. 250 l i (DMGA) perborate washing powder jl, 2
  • Soil to be eliminated difference between initial reflectance and that after formation of stains Soil eliminated: difference between reflectance after washing and that before washing.
  • Table 2a summarizes the values of Table 2, expressed surface active organic materials, 21
  • Example 5 Tests carried out with the object of determining the action of DMGA on the efficiency of proteolytic en- EXAMPLE 4 EXAMPLE 5 The tests of Example 5 were carried out under the same conditions as those indicated in Example 2. The
  • the water used in this example has a very high hardness of powders.
  • washing powder perborate (see Example 1 for composition g./1. '2 or pcrcarhonate (see Example 3 for composition) g./1. 1.88 proteolytic enzymes at 300,000 units Delft/g. g./1. 0.02 Test pieces to be washed (about 100 cm.):
  • EMPA 112 number 1 EMPA 116 number 1
  • the DMGA is used at the rate r0.4 g./1. of washin liquid.
  • Diagrams 2 and 3 relate to a concentration of activator of 0.25 g./I. while diagrams 4 and 5 were obtained with an activator concentration of 0.5 g./l.
  • Diagrams 2 and 4 relate to soaking tests with fabrics soiled with tea, diagrams 3 and 5 to fabrics soiled with red wine.
  • Curves I relate to tests carried out without activator, curves II to tests carried out with DMGA, III with DAG and IV with MEGA.
  • Table 6 expresses these results in terms of relative ef ficiency.
  • Table 6a indicates the time required for a soaking Table 6 Nature of Concentration of Relative Efficiency After 3 hours Activator Activator of Soaking:
  • DAG diacetylated glyoximc
  • MEGA diucctylatcd methylcthylglyoximc
  • a process for the activation, in an aqueous medium, of an active oxygen releasing compound selected from the group consisting of hydrogen peroxide, sodium perborate and sodium percarbonate which comprises activating said active oxygen releasing compound by an activator selected from the group consisting of diacylated glyoxime and diacylated dialkylglyoxime wherein the alkyl group contains from one to four carbon atoms and the acyl group contains from two to four carbon atoms, said activator being present in a quantity corresponding to about 0.05-1 mole per gramatom of active oxygen contained in said active oxygen releasing compound.
  • ide compound is hydrogen peroxide.
  • a solid composition for producing-washing and bleaching baths by dissolution in water comprising an active oxygen releasing compound selected from the group consisting of sodium perborate and sodium percarbonate and an activator selected from the group consisting of diacylated glyoxime, diacylated dialkylglyoxime wherein the alkyl group contains from one to four carbon atoms and the acyl group contains from two to four carbon atoms, said activator being present in a quantity corresponding to about 0.05-1 mole per gram-atom of active oxygen contained in said active oxygen releasing compound.
US00146932A 1970-05-27 1971-05-26 Activation of peroxide washing and bleaching baths Expired - Lifetime US3816319A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7019481A FR2087687A5 (fr) 1970-05-27 1970-05-27 Activation des bains de lavage et de blanchiment aux peroxydes

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US (1) US3816319A (de)
JP (1) JPS5519960B1 (de)
AT (1) AT326608B (de)
BE (1) BE766917A (de)
BR (1) BR7103186D0 (de)
CA (1) CA957308A (de)
CH (3) CH557446A (de)
DE (1) DE2124587C3 (de)
ES (1) ES391257A1 (de)
FR (1) FR2087687A5 (de)
GB (1) GB1300358A (de)
NL (1) NL166293C (de)
SE (1) SE375124B (de)
ZA (1) ZA713154B (de)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957670A (en) * 1973-12-04 1976-05-18 Hoechst Aktiengesellschaft Activators for inorganic per-compounds
US3975153A (en) * 1975-08-25 1976-08-17 Fmc Corporation Activation of peroxygen bleaches using isophorone enol acetates and isophorone oximinoacetate
US4021361A (en) * 1975-08-25 1977-05-03 Fmc Corporation Storage-stable detergent composition containing sodium perborate and activator
US4064062A (en) * 1975-12-15 1977-12-20 Colgate-Palmolive Stabilized activated percompound bleaching compositions and methods for manufacture thereof
US4164395A (en) * 1978-10-16 1979-08-14 Fmc Corporation Peroxygen bleaching and compositions therefor
USRE32672E (en) * 1985-09-09 1988-05-24 Allergan, Inc. Method for simultaneously cleaning and disinfecting contact lenses using a mixture of peroxide and proteolytic enzyme
US4778618A (en) * 1986-11-06 1988-10-18 The Clorox Company Glycolate ester peracid precursors
US4859800A (en) * 1986-11-06 1989-08-22 The Clorox Company Phenoxyacetate peracid precursors
US4956117A (en) * 1986-11-06 1990-09-11 The Clorox Company Phenoxyacetate peracid precursors and perhydrolysis systems therewith
US4957647A (en) * 1986-11-06 1990-09-18 The Clorox Company Acyloxynitrogen peracid precursors
US5049305A (en) * 1986-11-06 1991-09-17 Zielske Alfred G Phenoxyacetate peracid precursors and perhydrolysis systems therewith
US5328634A (en) * 1986-11-06 1994-07-12 The Clorox Company Acyloxynitrogen peracid precursors
US6025023A (en) * 1996-06-28 2000-02-15 Valente; Gabriele Method for decorating stone-like materials and a machine for carrying out this method
US6448062B1 (en) 1998-10-30 2002-09-10 Metrex Research Corporation Simultaneous cleaning and decontaminating compositions and methods
US6540960B2 (en) * 1996-12-11 2003-04-01 Henkel-Ecolab Gmbh & Co. Ohg (Henkel-Ecolab) Process for disinfecting instruments
US6596683B1 (en) 1998-12-22 2003-07-22 The Procter & Gamble Company Process for preparing a granular detergent composition
US6858572B1 (en) 1999-03-09 2005-02-22 The Procter & Gamble Company Process for producing coated detergent particles
US7022660B1 (en) 1999-03-09 2006-04-04 The Procter & Gamble Company Process for preparing detergent particles having coating or partial coating layers
EP2059581A2 (de) * 2006-08-15 2009-05-20 American Sterilizer Company Einteilige feststoffe mit zusammensetzungen aus dekontaminationsmischungen

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU604263B2 (en) * 1986-11-06 1990-12-13 Clorox Company, The Acyloxynitrogen peracid precursors

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957670A (en) * 1973-12-04 1976-05-18 Hoechst Aktiengesellschaft Activators for inorganic per-compounds
US3975153A (en) * 1975-08-25 1976-08-17 Fmc Corporation Activation of peroxygen bleaches using isophorone enol acetates and isophorone oximinoacetate
US4021361A (en) * 1975-08-25 1977-05-03 Fmc Corporation Storage-stable detergent composition containing sodium perborate and activator
US4064062A (en) * 1975-12-15 1977-12-20 Colgate-Palmolive Stabilized activated percompound bleaching compositions and methods for manufacture thereof
US4164395A (en) * 1978-10-16 1979-08-14 Fmc Corporation Peroxygen bleaching and compositions therefor
USRE32672E (en) * 1985-09-09 1988-05-24 Allergan, Inc. Method for simultaneously cleaning and disinfecting contact lenses using a mixture of peroxide and proteolytic enzyme
US5049305A (en) * 1986-11-06 1991-09-17 Zielske Alfred G Phenoxyacetate peracid precursors and perhydrolysis systems therewith
US4859800A (en) * 1986-11-06 1989-08-22 The Clorox Company Phenoxyacetate peracid precursors
US4956117A (en) * 1986-11-06 1990-09-11 The Clorox Company Phenoxyacetate peracid precursors and perhydrolysis systems therewith
US4957647A (en) * 1986-11-06 1990-09-18 The Clorox Company Acyloxynitrogen peracid precursors
US4778618A (en) * 1986-11-06 1988-10-18 The Clorox Company Glycolate ester peracid precursors
US5328634A (en) * 1986-11-06 1994-07-12 The Clorox Company Acyloxynitrogen peracid precursors
US5380457A (en) * 1986-11-06 1995-01-10 The Clorox Company Acyloxynitrogen peracid precursors
US6025023A (en) * 1996-06-28 2000-02-15 Valente; Gabriele Method for decorating stone-like materials and a machine for carrying out this method
US6540960B2 (en) * 1996-12-11 2003-04-01 Henkel-Ecolab Gmbh & Co. Ohg (Henkel-Ecolab) Process for disinfecting instruments
US6448062B1 (en) 1998-10-30 2002-09-10 Metrex Research Corporation Simultaneous cleaning and decontaminating compositions and methods
US20030100101A1 (en) * 1998-10-30 2003-05-29 Metrex Research Corporation Simultaneous cleaning and decontaminating compositions and methods
US6596683B1 (en) 1998-12-22 2003-07-22 The Procter & Gamble Company Process for preparing a granular detergent composition
US6858572B1 (en) 1999-03-09 2005-02-22 The Procter & Gamble Company Process for producing coated detergent particles
US7022660B1 (en) 1999-03-09 2006-04-04 The Procter & Gamble Company Process for preparing detergent particles having coating or partial coating layers
EP2059581A2 (de) * 2006-08-15 2009-05-20 American Sterilizer Company Einteilige feststoffe mit zusammensetzungen aus dekontaminationsmischungen
EP2059581A4 (de) * 2006-08-15 2012-07-04 American Sterilizer Co Einteilige feststoffe mit zusammensetzungen aus dekontaminationsmischungen

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Publication number Publication date
CH716371A4 (de) 1974-11-15
CH561807A (de) 1975-05-15
DE2124587A1 (de) 1971-12-09
JPS5519960B1 (de) 1980-05-29
ATA462071A (de) 1975-03-15
ZA713154B (en) 1972-01-26
DE2124587C3 (de) 1980-04-10
NL166293C (nl) 1981-07-15
NL7106739A (de) 1971-11-30
NL166293B (nl) 1981-02-16
DE2124587B2 (de) 1979-08-02
ES391257A1 (es) 1973-06-16
CH557446A (fr) 1974-12-31
BE766917A (fr) 1971-11-10
FR2087687A5 (fr) 1971-12-31
BR7103186D0 (pt) 1973-04-10
CA957308A (en) 1974-11-05
GB1300358A (en) 1972-12-20
AT326608B (de) 1975-12-29
SE375124B (de) 1975-04-07

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