WO2013178289A1 - Stabilisation d'acides phtalimido percarboxyliques à l'aide de sels de lithium - Google Patents

Stabilisation d'acides phtalimido percarboxyliques à l'aide de sels de lithium Download PDF

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Publication number
WO2013178289A1
WO2013178289A1 PCT/EP2012/060448 EP2012060448W WO2013178289A1 WO 2013178289 A1 WO2013178289 A1 WO 2013178289A1 EP 2012060448 W EP2012060448 W EP 2012060448W WO 2013178289 A1 WO2013178289 A1 WO 2013178289A1
Authority
WO
WIPO (PCT)
Prior art keywords
lithium
phthalimido
acid
mixture
mixture according
Prior art date
Application number
PCT/EP2012/060448
Other languages
English (en)
Inventor
Amila Bilic
Johannes Georg Winter
Original Assignee
Ecolab Usa Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ecolab Usa Inc. filed Critical Ecolab Usa Inc.
Priority to ES12725048.8T priority Critical patent/ES2595180T3/es
Priority to PCT/EP2012/060448 priority patent/WO2013178289A1/fr
Priority to EP12725048.8A priority patent/EP2855653B8/fr
Publication of WO2013178289A1 publication Critical patent/WO2013178289A1/fr

Links

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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/046—Salts
    • 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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/06—Phosphates, including polyphosphates
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • 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
    • C11D3/3937—Stabilising agents
    • 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
    • C11D3/3937—Stabilising agents
    • C11D3/394—Organic compounds

Definitions

  • the present invention relates to a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one lithium salt, to a detergent composition comprising said mixture, and to the use of at least one lithium salt for stabilizing a phthalimido percarboxylic acid in a detergent composition.
  • organic peracids have encountered increasing interest in the industrial field, among others due to their excellent properties as bleaching agents in detergent formulations. Therefore, a large number of publications are concerned with organic peracid compounds endowed with the required property of sufficient bleaching activity, said characteristic being essential for an industrial application and a widespread use of such compounds.
  • organic straight-chain or cyclic mono- or dipercarboxylic acids are known and used, e.g. in detergent compositions.
  • boric acid As boric acid has become a chemical of high concern, it is to be expected that boric acid will be banned from use in domestic applications in the near future.
  • the present invention satisfies this need by providing a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one lithium salt.
  • a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one lithium salt.
  • phthalimido percarboxylic acids can be stabilized by lithium salts. This is rather surprising since it was suggested by the prior art that phthalimido percarboxylic acids if not stabilized degrade following a radical reaction pathway.
  • phthalimido peroxyhexanoic acid phthalimido percaproic acid, PAP
  • PAP phthalimido percaproic acid
  • nucleophilic reaction sites at PAP and/or by catching nucleophiles with electrophiles other than PAP.
  • the present invention is directed to a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one lithium salt.
  • the at least one lithium salt may be either organic or inorganic.
  • the at least one lithium salt may be hydrous or anhydrous.
  • the present invention also relates to the mixture described above, characterized in that it comprises at least one inorganic lithium salt.
  • the present invention further relates to the mixture described above, characterized in that it comprises at least one organic lithium salt.
  • the anion of the at least one lithium salt is rather non-nucleophilic. If the anion in question is too nuc!eophilic, it is assumed to compete against the lithium cation for interaction with the phthalimido percarboxylic acid.
  • Suitable non-nucleophilic anions for use according to the present invention are hexafluorosilicate (SiF 6 2" ), sulfite (S0 3 2” ), hydrogensulfite (HS0 3 ⁇ ), organosulfite (RS0 3 ⁇ ), sulfate (S0 4 2” ), hydrogensulfate (HS0 4 " ), organosulfate (RS0 4 " ), phosphate (PO4 3 ), hydrogenphosphate (HPO4 2” ).
  • R is selected from the group of Ci to C30 substituted and unsubstituted, linear, branched, cyclic alkyl, alkenyl, aryl, alkylaryl, arylalkyl, alkenylaryl, arylalkenyl, and combinations thereof, wherein the sulfate anion represents the most preferred anion.
  • the present invention also relates to the mixture described above, characterized in that it comprises at least one lithium salt is selected from the group consisting of lithium hexafluorosilicate (L ⁇ SiFe), lithium sulfite (U2SO3), lithium hydrogensulfite (L1HSO3), lithium organosulfite (Li 2 RS0 3 ), lithium sulfate (Li 2 S0 4 ), lithium hydrogensulfate (LJHSO4), lithium organosulfate (LiRS0 4 ), lithium phosphate (Li 3 P0 4 ), lithium hydrogenphosphate ⁇ U2HPO4), lithium dihydrogenphosphate
  • LiPF 6 lithium hexachloro aluminate
  • Li 3 AICI 6 lithium hexabromo aluminate
  • Li 3 AIBr 6 lithium salt of an organic acid
  • R is selected from the group of Ci to C 30 substituted and unsubstituted, linear, branched, cyclic alkyl, alkenyl, aryl, alkylaryl, arylalkyl, alkenylaryl, arylalkenyl, and combinations thereof.
  • the present invention further relates to the mixture as described above, characterized in that it comprises lithium sulfate. Also, there is no restriction as concerns the chemical nature of the at least one phthalimido percarboxylic acid. Suitable phthalimido percarboxylic acids for use according to the present invention may be selected from the phthalimido
  • n is an integer of from 1 to 5:
  • phthalimido percaproic acid phthalimido percaproic acid (phthalimido peroxyhexanoic acid, PAP)
  • the present invention also relates to the mixture described above, characterized in that it comprises at least one phthalimido percarboxylic acid selected from the phthalimido percarboxylic acids of the general formula (I) above, where n is an integer of from 1 to 5.
  • the present invention further relates to the mixture described above, characterized in that it comprises phthalimido percaproic acid (phthalimido peroxyhexanoic acid, PAP).
  • Phthalimido percarboxylic acids and especially phthalimido peroxycarproic acid may be prepared as described in EP 0 325 288 A1 and EP 0 349 940 B1 , respectively.
  • a substrate selected from phthalimido carboxylic acids and anhydrides thereof having a structure corresponding to the desired percarboxylic acid, e.g. of the general formula (I) may be reacted with concentrated H2O2 in a reaction medium selected from concentrated H 2 S0 4 and CH3SO3H or in an alkaline medium, and the
  • percarboxylic acid is then separated from the reaction mixture by conventional and known techniques.
  • the content of lithium salt in the mixture should range between 1 and 50 % by weight, preferably between 1 and 25 % by weight, more preferably between 1 and 10 % by weight, most preferably between 2 and 5 % by weight based on the total weight of the mixture.
  • the present invention also relates to the mixture described above, characterized in that the content of lithium salt is between 1 and 50 % by weight, preferably between 1 and 25 % by weight, more preferably between 1 and 10 % by weight, most preferably between 2 and 5 % by weight based on the total weight of the mixture.
  • the weight ratio of phthalimido percarboxylic acid to lithium salt is between 20:1 and 1 :1 , preferably between 10:1 and 1 :1 , more preferably between 5:1 and 1 :1 , most preferably between 2:1 and 1 :1.
  • the present invention also relates to the mixture described above, characterized in that the weight ratio of phthalimido percarboxylic acid to lithium salt is between 20:1 and 1:1 , preferably between 10:1 and 1 :1 , more preferably between 5:1 and 1 :1 , most preferably between 2:1 and 1 :1.
  • An especially expedient mixture for use as a bleaching agent comprises between 10 and 25 % by weight of phthalimido peroxyhexanoic acid (phthalimido percaproic acid, PAP) and between 2 and 5 % by weight of lithium sulfate based on the total weight of the mixture.
  • the present invention also relates to the mixture described above, characterized in that it comprises between 10 and 25 % by weight of phthalimido peroxyhexanoic acid (phthalimido percaproic acid, PAP) and between 2 and 5 % by weight of lithium sulfate based on the total weight of the mixture.
  • phthalimido peroxyhexanoic acid phthalimido percaproic acid, PAP
  • lithium sulfate based on the total weight of the mixture.
  • the mixture comprising the at least one phthalimido percarboxylic acid and the at least one lithium salt according to the present invention may be manufactured in the form of an aqueous solution, gel, emulsion, paste, dispersion, powder, flake, granules, scales, pearls, tablets, solid block form, extrudates and other forms known in the art, but preferably represents a powder or a flake.
  • the present invention also relates to the mixture described above, characterized in that the mixture is in the form of a powder or a flake.
  • the mixture according to the present invention is particularly suitable as effective bleaching agent in detergent formulations.
  • the present invention is also directed to the use of a mixture described above as a bleaching agent.
  • the present invention is further directed to a detergent composition comprising a mixture described above.
  • the detergent composition may contain any additive or active ingredient commonly used in corresponding washing, cleansing and/or disinfecting agents like builders, surfactants, soaps, zeolites, hydrotropic agents, corrosion inhibitors, enzymes, optical brighteners, stabilizers, abrasives, perfumes, coloring agents.
  • inventive mixture may be incorporated into the detergent composition either as such or in combination with further additives, for example phosphates, carbonates, zeolites, carboxymethylcellulose or filmbuilding agents like fatty acids, fatty acid amides or esters etc. in the forms mentioned above for the mixture.
  • further additives for example phosphates, carbonates, zeolites, carboxymethylcellulose or filmbuilding agents like fatty acids, fatty acid amides or esters etc.
  • the detergent composition is substantially free of boric acid, i.e. comprises less than 10 ppm, preferably less than 5 ppm, even more preferably less than 1 ppm, and most preferably less than 0,1 ppm boric acid.
  • the present invention also relates to the detergent composition described before, characterized in that it comprises less than 10 ppm, preferably less than 5 ppm, even more preferably less than 1 ppm, and most preferably less than 0,1 ppm boric acid.
  • the detergent composition may be used as a laundry detergent, preferably as a textile detergent, and is not only suitable for generally washing laundry, but as well for disinfecting.
  • the detergent according to the present application may be used as cleanser and/or disinfectant for cleansing and disinfecting various kinds of hard surfaces like, for example, in the medicinal or institutional field, in the food preparing, processing and/or selling industry, in agriculture, in hotel business, catering trade and/or in public buildings and/or institutions. It may as well be useful in further applications in which a disinfected surface is required or desired and which are not explicitly mentioned herein.
  • the surfaces supposed to become disinfected may be made of common materials mentioned in the state of the art like, for example, metal, glass, ceramic, plastic, (coated) wood.
  • the present invention relates to the use of at least one lithium salt for stabilizing a phthalimido percarboxy!ic acid in a detergent composition.
  • a mixture for use as a bleaching agent comprising 86 % by weight of phthalimido peroxyhexanoic acid (phthalimido percaproic acid, PAP) and 14 % by weight of a stabilizing agent (example 1a: boric acid (comparative); example 1 b: sodium sulfate (comparative); example 1c: lithium sulfate) was tested for its long-term stability. Therefore, the amount of chemically active PAP in the respective mixture was determined after storage by 40 °C at 1 , 3, 7, 14, 21 , 28, 49, 84, 119, 161 and 2 0 days, respectively.
  • a mixture comprising lithium sulfate shows a significantly higher long-term stability of phthalimido peroxyhexanoic acid (phthalimido percaproic acid, PAP) than a mixture comprising sodium sulfate (example 1b).
  • phthalimido peroxyhexanoic acid phthalimido percaproic acid, PAP
  • a lithium salt according to the present invention example 1c
  • boric acid conventionally used example 1a

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)

Abstract

La présente invention concerne un mélange destiné à être utilisé en tant qu'agent de blanchiment et comprenant au moins un acide phtalimido percarboxylique et au moins un sel de lithium, une composition détergente comprenant ledit mélange, et concerne l'utilisation d'au moins un sel de lithium pour stabiliser un acide phtalimido percarboxylique dans une composition détergente.
PCT/EP2012/060448 2012-06-01 2012-06-01 Stabilisation d'acides phtalimido percarboxyliques à l'aide de sels de lithium WO2013178289A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
ES12725048.8T ES2595180T3 (es) 2012-06-01 2012-06-01 Estabilización de ácidos ftalimido percarboxílicos con sales de litio
PCT/EP2012/060448 WO2013178289A1 (fr) 2012-06-01 2012-06-01 Stabilisation d'acides phtalimido percarboxyliques à l'aide de sels de lithium
EP12725048.8A EP2855653B8 (fr) 2012-06-01 2012-06-01 Stabilisation d'acides phtalimido percarboxyliques à l'aide de sels de lithium

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2012/060448 WO2013178289A1 (fr) 2012-06-01 2012-06-01 Stabilisation d'acides phtalimido percarboxyliques à l'aide de sels de lithium

Publications (1)

Publication Number Publication Date
WO2013178289A1 true WO2013178289A1 (fr) 2013-12-05

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PCT/EP2012/060448 WO2013178289A1 (fr) 2012-06-01 2012-06-01 Stabilisation d'acides phtalimido percarboxyliques à l'aide de sels de lithium

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Country Link
EP (1) EP2855653B8 (fr)
ES (1) ES2595180T3 (fr)
WO (1) WO2013178289A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0325288A1 (fr) 1988-01-20 1989-07-26 AUSIMONT S.p.A. Acides percarboxyliques imido-aromatiques
EP0349940B1 (fr) 1988-07-08 1998-05-13 Clariant GmbH Phthalimidohexanpéracide, procédé pour sa préparation et son application
EP1586628A1 (fr) * 2004-04-05 2005-10-19 The Procter & Gamble Company Compositions particulaires de blanchiment
WO2006000344A1 (fr) * 2004-06-25 2006-01-05 Henkel Kommanditgesellschaft Auf Aktien Production de compositions d'acide peroxycarboxylique particulaires
WO2006120405A1 (fr) * 2005-05-09 2006-11-16 Reckitt Benckiser N.V. Composition detergente
JP2010138268A (ja) * 2008-12-11 2010-06-24 Kao Corp 液体漂白洗浄剤組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0325288A1 (fr) 1988-01-20 1989-07-26 AUSIMONT S.p.A. Acides percarboxyliques imido-aromatiques
EP0349940B1 (fr) 1988-07-08 1998-05-13 Clariant GmbH Phthalimidohexanpéracide, procédé pour sa préparation et son application
EP1586628A1 (fr) * 2004-04-05 2005-10-19 The Procter & Gamble Company Compositions particulaires de blanchiment
WO2006000344A1 (fr) * 2004-06-25 2006-01-05 Henkel Kommanditgesellschaft Auf Aktien Production de compositions d'acide peroxycarboxylique particulaires
WO2006120405A1 (fr) * 2005-05-09 2006-11-16 Reckitt Benckiser N.V. Composition detergente
JP2010138268A (ja) * 2008-12-11 2010-06-24 Kao Corp 液体漂白洗浄剤組成物

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEM. IND., 1961, pages 469
J. CHEM. SOC., 1962, pages 3821

Also Published As

Publication number Publication date
EP2855653B8 (fr) 2016-12-07
ES2595180T3 (es) 2016-12-28
EP2855653A1 (fr) 2015-04-08
EP2855653B1 (fr) 2016-07-20

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