WO2013178290A1 - Stabilisation d'acides phtalimido percarboxyliques à l'aide de disaccharides - Google Patents

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

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Publication number
WO2013178290A1
WO2013178290A1 PCT/EP2012/060449 EP2012060449W WO2013178290A1 WO 2013178290 A1 WO2013178290 A1 WO 2013178290A1 EP 2012060449 W EP2012060449 W EP 2012060449W WO 2013178290 A1 WO2013178290 A1 WO 2013178290A1
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WO
WIPO (PCT)
Prior art keywords
phthalimido
mixture
acid
disaccharide
weight
Prior art date
Application number
PCT/EP2012/060449
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/EP2012/060449 priority Critical patent/WO2013178290A1/fr
Priority to EP12726408.3A priority patent/EP2855654A1/fr
Publication of WO2013178290A1 publication Critical patent/WO2013178290A1/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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/221—Mono, di- or trisaccharides or derivatives 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
    • 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 mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one disaccharide, to a detergent composition comprising said mixture, and to the use of at least one disaccharide 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 disaccharide.
  • a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one disaccharide.
  • phthalimido percarboxylic acids can be stabilized by disaccharides. 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 disaccharide.
  • the at least one disaccharide may be either a reducing or non- reducing disaccharide.
  • the at least one disaccharide may be hydrous or anhydrous.
  • the present invention also relates to the mixture described above, characterized in that it comprises at least one reducing disaccharide.
  • the present invention further relates to the mixture described above, characterized in that it comprises at least one non-reducing disaccharide.
  • Suitable disaccharides for use according to the present invention are cellobiose, gentiobiose, isomaltose, isomaltulose, lactose, lactulose, iaminaribiose, maltose, maltulose, melibiose, neohesperidose, neotrehalose, nigeriose, rutinose, sophorose, saccharose, and trehalose, wherein lactose represents the most preferred
  • the present invention also relates to the mixture described above, characterized in that it comprises at least one disaccharide selected from the group consisting of cellobiose, gentiobiose, isomaltose, isomaltulose, lactose, lactulose, Iaminaribiose, maltose, maltulose, melibiose, neohesperidose, neotrehalose, nigeriose, rutinose, sophorose, saccharose, trehalose, and combinations thereof.
  • the present invention further relates to the mixture as described above, characterized in that it comprises lactose.
  • Suitable phthalimido percarboxylic acids for use according to the present invention may be selected from the phthalimido
  • 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 percarboxylic acids and especially phthalimido peroxycaproic 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 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 disaccharide 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 disaccharide is between 1 and 50 % by weight, preferably between 1 and 25 % by weight, more preferably between 1 and 0 % 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 disaccharide 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
  • disaccharide is between 20:1 and 1 :1 , preferably between 0:1 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 lactose based on the total weight of the mixture. Therefore, 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 lactose based on the total weight of the mixture.
  • the mixture comprising the at least one phthalimido percarboxylic acid and the at least one disaccharide 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 solid or a flake.
  • the mixture according to the present invention is particularly suitable as effective bleaching agent in detergent formulations.
  • the present invention also relates to the use of a mixture described above as a bleaching agent.
  • the present invention further relates to a detergent composition
  • 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. Therefore, the present invention aiso 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 disaccharide 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 a: boric acid (comparative); example 1 b: glucose
  • example 1d lactose

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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)
  • Health & Medical Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)

Abstract

La présente invention concerne un mélange destiné à être utilisé en tant qu'agent de blanchiment, comprenant au moins un acide phtalimido percarboxylique et au moins un disaccharide, une composition détergente comprenant ledit mélange, et concerne l'utilisation d'au moins un disaccharide pour stabiliser un acide phtalimido percarboxylique dans une composition détergente.
PCT/EP2012/060449 2012-06-01 2012-06-01 Stabilisation d'acides phtalimido percarboxyliques à l'aide de disaccharides WO2013178290A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/EP2012/060449 WO2013178290A1 (fr) 2012-06-01 2012-06-01 Stabilisation d'acides phtalimido percarboxyliques à l'aide de disaccharides
EP12726408.3A EP2855654A1 (fr) 2012-06-01 2012-06-01 Stabilisation d'acides phtalimido percarboxyliques à l'aide de disaccharides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2012/060449 WO2013178290A1 (fr) 2012-06-01 2012-06-01 Stabilisation d'acides phtalimido percarboxyliques à l'aide de disaccharides

Publications (1)

Publication Number Publication Date
WO2013178290A1 true WO2013178290A1 (fr) 2013-12-05

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PCT/EP2012/060449 WO2013178290A1 (fr) 2012-06-01 2012-06-01 Stabilisation d'acides phtalimido percarboxyliques à l'aide de disaccharides

Country Status (2)

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EP (1) EP2855654A1 (fr)
WO (1) WO2013178290A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160122790A (ko) * 2014-02-10 2016-10-24 리볼리머 (유.케이.)리미티드 신규한 과산-함유 입자

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
EP1760141A1 (fr) * 2005-09-06 2007-03-07 SOLVAY (Société Anonyme) Peroxycarboxylique acide granulé enveloppé, procédé de préparation et utilisation dans la blanchissage, le blanchiment et la désinfection
US20080161218A1 (en) * 2005-05-09 2008-07-03 Reckitt Benckiser N.V. Detergent Composition
WO2012066344A1 (fr) * 2010-11-19 2012-05-24 Reckitt Benckiser N.V. Matériaux de blanchiment revêtus et colorés

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
US20080161218A1 (en) * 2005-05-09 2008-07-03 Reckitt Benckiser N.V. Detergent Composition
EP1760141A1 (fr) * 2005-09-06 2007-03-07 SOLVAY (Société Anonyme) Peroxycarboxylique acide granulé enveloppé, procédé de préparation et utilisation dans la blanchissage, le blanchiment et la désinfection
WO2012066344A1 (fr) * 2010-11-19 2012-05-24 Reckitt Benckiser N.V. Matériaux de blanchiment revêtus et colorés

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 (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160122790A (ko) * 2014-02-10 2016-10-24 리볼리머 (유.케이.)리미티드 신규한 과산-함유 입자
EP3105310B1 (fr) * 2014-02-10 2020-05-27 Società Chimica Bussi S.p.A. Nouvelle particule contenant un peracide
KR102151061B1 (ko) 2014-02-10 2020-09-03 소치에타 키미카 부시 에스피에이 신규한 과산-함유 입자

Also Published As

Publication number Publication date
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