EP2855653B1 - Stabilisierung von phthalimidpercarbonsäure mit lithiumsalzen - Google Patents

Stabilisierung von phthalimidpercarbonsäure mit lithiumsalzen Download PDF

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Publication number
EP2855653B1
EP2855653B1 EP12725048.8A EP12725048A EP2855653B1 EP 2855653 B1 EP2855653 B1 EP 2855653B1 EP 12725048 A EP12725048 A EP 12725048A EP 2855653 B1 EP2855653 B1 EP 2855653B1
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Prior art keywords
lithium
phthalimido
acid
mixture
weight
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EP2855653B8 (de
EP2855653A1 (de
Inventor
Amila Bilic
Johannes Georg Winter
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Ecolab USA Inc
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Ecolab USA Inc
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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
    • C11D3/02—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 inorganic 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. Consequently, there is a need for alternative ways of stabilizing phthalimido percarboxylic acids in detergent compositions without making use of boric acid.
  • 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 inorganic lithium salt.
  • a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one inorganic lithium salt.
  • phthalimido percarboxylic acids can be stabilized by inorganic 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 percarboxylic acids in fact degrade by attack of nucleophiles.
  • a plausible degradation scheme of phthalimido peroxyhexanoic acid (phthalimido percaproic acid, PAP) in alkaline conditions is shown in figure 1 .
  • PAP phthalimido percaproic acid
  • FIG 1 A plausible degradation scheme of phthalimido peroxyhexanoic acid (phthalimido percaproic acid, PAP) in alkaline conditions is shown in figure 1 .
  • PAP phthalimido percaproic acid
  • PAP phthalimido percaproic acid
  • 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 inorganic lithium salt.
  • the at least one lithium salt is organic.
  • 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 anion of the at least one lithium salt is rather non-nucleophilic. If the anion in question is too nucleophilic, 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 (SO 3 2- ), hydrogensulfite (HSO 3 - ), sulfate (SO 4 2- ), hydrogensulfate (HSO 4 - ), phosphate (PO 4 3- ), hydrogenphosphate (HPO 4 2- ), dihydrogenphosphate (H 2 PO 4 - ), tetrafluoro borate (BF 4 - ), tetrachloro borate (BCl 4 - ), tetrabromo borate (BBr 4 - ), tetraiodo borate (Bl 4 - ), tetraphenyl borate (B[C 6 H 5 ] 4 - ), tetra(pentafluoro)phenyl borate (B[C 6 F 5 ] 4 - ), hexafluorophosphate (PF 6 -
  • 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 (Li 2 SiF 6 ), lithium sulfite (Li 2 SO 3 ), lithium hydrogensulfite (LiHSO 3 ), lithium sulfate (Li 2 SO 4 ), lithium hydrogensulfate (LiHSO 4 ), lithium phosphate (Li 3 PO 4 ), lithium hydrogenphosphate (Li 2 HPO 4 ), lithium dihydrogenphosphate (LiH 2 PO 4 ), lithium tetrafluoro borate (LiBF 4 ), lithium tetrachloro borate (LiBCl 4 ), lithium tetrabromo borate (LiBBr 4 ), lithium tetraiodo borate (LiBl 4 ), lithium tetraphenyl borate (LiB[C 6 H 5 ] 4 ), lithium tetra(pentafluor
  • Suitable phthalimido percarboxylic acids for use according to the present invention may be selected from the phthalimido percarboxylic acids of the general formula (I), where n is an integer of from 1 to 5:
  • phthalimido percaproic acid phthalimido percaproic acid (phthalimido peroxyhexanoic acid, PAP) represents
  • 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 (1) 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 H 2 O 2 in a reaction medium selected from concentrated H 2 SO 4 and CH 3 SO 3 H 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 percarboxylic 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 1b: 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 210 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).
  • Table 1 Activity of PAP % Days 0 1 3 7 14 21 28 49 84 119 161 210 PAP by 40 °C with Boric acid 14 % 84,4 84,3 82,2 84,0 81,4 83,3 79,7 81,2 77,2 73,3 73,6 74,0 PAP by 40 °C with Sodium sulfate 14 % 84,5 80,2 78,7 75,5 78,2 77,3 77,3 75,3 73,6 72,8 72,0 70,8 PAP by 40°C with Lithium sulfate 14 % 84.6 78,3 81,1 83,9 76,9 83,8 82,0 80,8 79,8 79,8 77,7 77,3
  • phthalimido peroxyhexanoic acid phthalimido percaproic acid, PAP
  • PAP phthalimido percaproic acid

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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)

Claims (13)

  1. Gemisch zur Verwendung als Bleichmittel, umfassend wenigstens eine Phthalimidopercarbonsäure und wenigstens ein anorganisches Lithiumsalz.
  2. Gemisch nach Anspruch 1, dadurch gekennzeichnet, dass dieses wenigstens ein Lithiumsalz umfasst, ausgewählt aus der Gruppe bestehend aus Lithiumhexafluorosilikat (Li2SiF6), Lithiumsulfit (Li2SO3), Lithiumhydrogensulfit (LiHSO3), Lithiumsulfat (Li2SO4), Lithiumhydrogensulfat (LiHSO4), Lithiumphosphat (Li3PO4), Lithiumhydrogenphosphat (Li2HPO4), Lithiumdihydrogenphosphat (LiH2PO4), Lithiumtetrafluorborat (LiBF4), Lithiumtetrachlorborat (LiBCl4), Lithiumtetrabromborat (LiBBr4), Lithiumtetraiodborat (LiBI4), Lithiumtetraphenylborat (LiB[C6H5]4), Lithiumtetrakis(pentafluor)phenylborat (LiB[C6F5]4), Lithiumhexafluorphosphat (LiPF6), Lithiumhexachloraluminat (Li3AlCl6), Lithiumhexabromaluminat (Li3AlBr6) sowie Kombinationen davon.
  3. Gemisch nach einem der Ansprüche 1 oder 2, dadurch gekennzeichnet, dass dieses Lithiumsulfat umfasst.
  4. Gemisch nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass dieses wenigstens eine Phthalimidopercarbonsäure umfasst, ausgewählt unter den Phthalimidopercarbonsäuren der allgemeinen Formel (I)
    Figure imgb0003
     worin n eine Ganzzahl von 1 bis 5 ist.
  5. Gemisch nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass dieses Phthalimidoperoxyhexansäure (Phthalimidopercapronsäure, PAP) umfasst.
  6. Gemisch nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass der Gehalt an Lithiumsalz zwischen 1 und 50 Gew.-% liegt, vorzugsweise zwischen 1 und 25 Gew.-%, bevorzugter zwischen 1 und 10 Gew.-%, am meisten bevorzugt zwischen 2 und 5 Gew.-%, basierend auf dem Gesamtgewicht des Gemisches.
  7. Gemisch nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass das Gewichtsverhältnis von Phthalimidopercarbonsäure zu Lithiumsalz zwischen 20:1 und 1:1 liegt, vorzugsweise zwischen 10:1 und 1:1, bevorzugter zwischen 5:1 und 1:1, am meisten bevorzugt zwischen 2:1 und 1:1.
  8. Gemisch nach einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, dass dieses zwischen 10 und 25 Gew.-% an Phthalimidoperoxyhexansäure (Phthalimidopercapronsäure, PAP) umfasst und zwischen 2 und 5 Gew.-% an Lithiumsulfat, basierend auf dem Gesamtgewicht des Gemisches.
  9. Gemisch nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass das Gemisch in Form eines Pulvers oder als Flocken vorliegt.
  10. Verwendung eines Gemisches nach einem der Ansprüche 1 bis 9 als Bleichmittel.
  11. Detergenszusammensetzung, umfassend das Gemisch nach einem der Ansprüche 1 bis 9.
  12. Detergenszusammensetzung nach Anspruch 11, dadurch gekennzeichnet, dass diese weniger als 10 ppm, vorzugsweise weniger als 5 ppm, noch mehr bevorzugt weniger als 1 ppm und am meisten bevorzugt weniger als 0,1 ppm an Borsäure umfasst.
  13. Verwendung von wenigstens einem anorganischen Lithiumsalz zur Stabilisierung einer Phthalimidopercarbonsäure in einer Detergenszusammensetzung.
EP12725048.8A 2012-06-01 2012-06-01 Stabilisierung von phthalimidpercarbonsäure mit lithiumsalzen Active EP2855653B8 (de)

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PCT/EP2012/060448 WO2013178289A1 (en) 2012-06-01 2012-06-01 Stabilization of phthalimido percarboxylic with lithium salts

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EP2855653B1 true EP2855653B1 (de) 2016-07-20
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Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1233846B (it) 1988-01-20 1992-04-21 Ausimont Spa Perossiacidi immido aromatici
DE3823172C2 (de) 1988-07-08 1998-01-22 Hoechst Ag omega-Phthalimidoperoxihexansäure, Verfahren zu dessen Herstellung und dessen Verwendung
EP1586628A1 (de) * 2004-04-05 2005-10-19 The Procter & Gamble Company Teilchenförmige Bleichmittelzusammensetzungen
DE102004030900A1 (de) * 2004-06-25 2006-01-26 Henkel Kgaa Herstellung teilchenförmiger Peroxycarbonsäurezusammensetzungen
GB0509377D0 (en) * 2005-05-09 2005-06-15 Reckitt Benckiser Nv Detergent composition
JP2010138268A (ja) * 2008-12-11 2010-06-24 Kao Corp 液体漂白洗浄剤組成物

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EP2855653A1 (de) 2015-04-08
ES2595180T3 (es) 2016-12-28
WO2013178289A1 (en) 2013-12-05

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