WO2014183795A1 - Stabilisation d'acides phtalimido percarboxyliques par des acides aminoalcanesulfoniques - Google Patents

Stabilisation d'acides phtalimido percarboxyliques par des acides aminoalcanesulfoniques Download PDF

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Publication number
WO2014183795A1
WO2014183795A1 PCT/EP2013/060248 EP2013060248W WO2014183795A1 WO 2014183795 A1 WO2014183795 A1 WO 2014183795A1 EP 2013060248 W EP2013060248 W EP 2013060248W WO 2014183795 A1 WO2014183795 A1 WO 2014183795A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
phthalimido
composition
aminoalkanesulfonic
acids
Prior art date
Application number
PCT/EP2013/060248
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 PCT/EP2013/060248 priority Critical patent/WO2014183795A1/fr
Publication of WO2014183795A1 publication Critical patent/WO2014183795A1/fr

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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
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
    • 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
    • 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

Definitions

  • the present invention relates to a composition for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one
  • aminoalkanesulfonic acid to a detergent composition comprising said composition, and to the use of at least one aminoalkanesulfonic acid for stabilizing a phthalimido percarboxylic acid in a detergent composition.
  • Phthalimido percarboxylic acids are used in detergents as bleaching agents and for disinfecting washing.
  • 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 composition for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one aminoalkanesulfonic acid.
  • a composition for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one aminoalkanesulfonic acid.
  • phthalimido percarboxylic acids can be stabilized by aminoalkanesulfonic acids. Without wishing to be bound to any theory, it is assumed that phthalimido percarboxylic acids either degrade following a radical reaction pathway, or degrade under attack of nucleophiles.
  • Two plausible degradation schemes of phthalimido peroxyhexanoic acid (phthalimido percaproic acid, PAP) are shown in figures 1 and 2. According to figure 1 , PAP is degraded to phthalimido caproic acid and carbon dioxide following a radical reaction pathway.
  • PAP is degraded by an intra molecular reaction: the slightly nucleophilic nitrogen atom of the phthalimide moiety attacks the electrophilic carbon atom of the peracid moiety.
  • the presence of at least one aminoalkanesulfonic acid would prevent degradation of PAP either by stopping radical degradation in its capacity as antioxidant, by stopping the intra molecular reaction in its capacity as strong electrophile, or by stopping the decomposition in its capacity as pH regulator.
  • the present invention is directed to a composition for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one aminoalkanesulfonic acid.
  • a composition for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one aminoalkanesulfonic acid.
  • Suitable aminoalkanesulfonic acids for use according to the present invention may be selected from the aminoalkanesulfonic acids of the general formula (I), where m is an integer of from 1 to 5, preferably from 1 to 3.
  • the present invention also relates to the composition described above, characterized in that it comprises at least one aminoalkanesulfonic acid of the general formula (I) above, where m is an integer of from 1 to 5, preferably 1 to 3.
  • the present invention further relates to the composition described above, characterized in that it comprises 2-aminoethanesuifonic acid (taurine) and/or 3-aminopropanesulfonic acid (homotaurine).
  • Suitable phthalimido percarboxylic acids for use according to the present invention may be selected from the phthalimido
  • phthalimido percaproic acid phthalimido percaproic acid (phthalimido peroxyhexanoic acid, PAP) represents
  • the present invention also relates to the composition described above, characterized in that it comprises at least one phthalimido percarboxylic acid selected from the phthalimido percarboxylic acids of the general formula (II) above, where n is an integer of from 1 to 5.
  • the present invention further relates to the composition 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 composition by conventional and known techniques.
  • the content of aminoalkanesulfonic acid in the composition 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 composition.
  • the present invention also relates to the compositions described above, characterized in that the content of aminoalkanesulfonic acid 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 compositions.
  • aminoalkanesulfonic acid 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. Therefore, the present invention also relates to the compositions described above, characterized in that the weight ratio of phthalimido percarboxylic acid to
  • aminoalkanesulfonic acid 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 composition 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 2-aminoethanesulfonic acid based on the total weight of the composition.
  • PAP phthalimido percaproic acid
  • the present invention also relates to the composition 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 adipic acid or isophthalic acid based on the total weight of the composition.
  • phthalimido percaproic acid phthalimido percaproic acid
  • compositions comprising the at least one phthalimido percarboxylic acid and the at least one aminoalkanesulfonic acid 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 compositions described above, characterized in that the composition is in the form of a powder, a flake or solid block.
  • composition 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 composition described above as a bleaching agent.
  • the present invention is further directed to a detergent composition
  • a detergent composition comprising a composition 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.
  • the inventive composition 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 composition.
  • 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 purposes.
  • 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 aminoalkanesulfonic acid for stabilizing a phthalimido percarboxylic acid in a detergent composition.
  • phthalimido peroxyhexanoic acid phthalimido percaproic acid, PAP
  • PAP phthalimido percaproic acid
  • Eltra 40 is a detergent in powder form which is used for disinfecting washing of laundry.
  • the tested detergent comprises 18,4 wt-% of PAP.
  • taurine (2-aminoethanesulfonic acid) was tested as stabilizing agent.
  • boric acid and ascorbic acid were used as stabilizing agents in the detergent Eltra 40. The following table shows the results.
  • the concentration of the stabilizing agent in the detergent composition was 3,64 wt- %.
  • example 1a taurine
  • example b boric acid comparative
  • example 1c ascorbic acid (comparative).
  • the concentration of chemically active PAP in the respective mixture was determined after storage by 35 °C at 1 , 3, 8, 10, 15, 18, 21 , 24, and 28 days, respectively.
  • Table 1 shows that the stabilization with taurine is better than with the stabilizer boric acid. Especially after longer storage times of more than 18 days the stabilization with taurine is surprisingly better than with boric acid which is used in the state of art as stabilizing agent. Ascorbic acid already shows a complete degradation of PAP after 24 days.

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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)
  • Detergent Compositions (AREA)

Abstract

La présente invention concerne une composition pour une utilisation comme agent de blanchiment comprenant au moins un acide phtalimido percarboxylique et au moins un acide aminoalcanesulfonique, une composition détergente comprenant ladite composition et l'utilisation d'au moins un acide aminoalcanesulfonique pour stabiliser un acide phtalimido percarboxylique dans une composition détergente.
PCT/EP2013/060248 2013-05-17 2013-05-17 Stabilisation d'acides phtalimido percarboxyliques par des acides aminoalcanesulfoniques WO2014183795A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/EP2013/060248 WO2014183795A1 (fr) 2013-05-17 2013-05-17 Stabilisation d'acides phtalimido percarboxyliques par des acides aminoalcanesulfoniques

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2013/060248 WO2014183795A1 (fr) 2013-05-17 2013-05-17 Stabilisation d'acides phtalimido percarboxyliques par des acides aminoalcanesulfoniques

Publications (1)

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WO2014183795A1 true WO2014183795A1 (fr) 2014-11-20

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020060434A1 (fr) * 2018-09-20 2020-03-26 Solvay Sa Composition de rupture pour fracturation à l'huile

Citations (5)

* 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
EP0509382A2 (fr) * 1991-04-17 1992-10-21 Hampshire Chemical Corporation Stabilisateurs de blanchiment biodégradables pour détergents
EP0349940B1 (fr) 1988-07-08 1998-05-13 Clariant GmbH Phthalimidohexanpéracide, procédé pour sa préparation et son application
WO2004110610A1 (fr) * 2003-06-13 2004-12-23 Henkel Kommanditgesellschaft Auf Aktien Procede permettant de stabiliser des acides peroxycarboxyliques dans des dispersions contenant des agents de surface
WO2011110849A1 (fr) * 2010-03-09 2011-09-15 Reckitt Benckiser N.V. Composition détergente

Patent Citations (5)

* 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
EP0509382A2 (fr) * 1991-04-17 1992-10-21 Hampshire Chemical Corporation Stabilisateurs de blanchiment biodégradables pour détergents
WO2004110610A1 (fr) * 2003-06-13 2004-12-23 Henkel Kommanditgesellschaft Auf Aktien Procede permettant de stabiliser des acides peroxycarboxyliques dans des dispersions contenant des agents de surface
WO2011110849A1 (fr) * 2010-03-09 2011-09-15 Reckitt Benckiser N.V. Composition détergente

Non-Patent Citations (2)

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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020060434A1 (fr) * 2018-09-20 2020-03-26 Solvay Sa Composition de rupture pour fracturation à l'huile

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