EP2407529A1 - Composition de peroxygène - Google Patents

Composition de peroxygène Download PDF

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Publication number
EP2407529A1
EP2407529A1 EP10169207A EP10169207A EP2407529A1 EP 2407529 A1 EP2407529 A1 EP 2407529A1 EP 10169207 A EP10169207 A EP 10169207A EP 10169207 A EP10169207 A EP 10169207A EP 2407529 A1 EP2407529 A1 EP 2407529A1
Authority
EP
European Patent Office
Prior art keywords
composition
carbon atoms
peracid
independently
quaternary ammonium
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP10169207A
Other languages
German (de)
English (en)
Inventor
Thomas E. Candy
Joseph W. Malone
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Solvay SA
Original Assignee
Solvay SA
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 Solvay SA filed Critical Solvay SA
Priority to EP10169207A priority Critical patent/EP2407529A1/fr
Priority to PCT/EP2011/061601 priority patent/WO2012007377A2/fr
Publication of EP2407529A1 publication Critical patent/EP2407529A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/835Mixtures of non-ionic with cationic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39Organic or inorganic per-compounds
    • C11D3/3945Organic per-compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/72Ethers of polyoxyalkylene glycols

Definitions

  • This invention concerns peroxygen compositions. More specifically, this invention concerns solutions of peracids and additives such as quaternary ammonium salts.
  • Peracids and peracid compositions are rapid acting oxidising biocides.
  • Perestane TM is an aqueous mixture comprising peracids.
  • Perestane TM is typically an aqueous equilibrium mixture comprising mixed peracids.
  • Perestane TM can be formulated into compositions which are effective low temperature bleaches, colourless, non-staining liquids which are easily rinsed from surfaces without leaving a residue.
  • Compositions including Perestane TM or other peracids may also be thickened or perfumed.
  • Perestane TM containing compositions or other compositions containing peracids are effective instantly and react quickly with the microbial agent thereafter decomposing quickly leaving no residue.
  • Perestane TM and other peracids are typically used as household disinfectants and surface cleaners.
  • Quaternary ammonium salts are effective disinfecting agents active against microbial agents, e.g. yeast, virus, bacteria, moulds and spores.
  • microbial agents e.g. yeast, virus, bacteria, moulds and spores.
  • quaternary ammonium salts have been used as antimicrobial agents for cleaning agents and for fabric softeners ( US 2003/0109403 ). Quats have also been used in compositions to reduce the antimicrobial burden in food products ( US 2002/0192340 ).
  • Quats have a longer lasting effect and provide disinfectant efficacy over a longer time period.
  • aqueous compositions containing peracids such as Perestane TM
  • peracids such as Perestane TM
  • quaternary ammonium salts and/or surfactants which lead respectively to a longer term effect and better wetting properties, which will both result in a better efficacy or performance as biocide.
  • formulation of peroxygen compounds is known to be difficult.
  • the additive needs to be resistant to oxidation (as it will be in presence of powerful oxidant) and also it must not destabilize the peroxygen compound giving rise to oxygen evolution and lack of activity (as measured by available oxygen "AvOx").
  • the addition of quaternary ammonium salts and/or of surfactants to peracids is known to cause destabilisation of the peracids leading to loss of efficacy in the short term.
  • an aqueous composition comprising at least:
  • R 1 may further be of the formula [R 6 -O] p wherein p is from 1 to 10, in particular from 2 to 5.
  • R 6 may for instance have from 1 to 5 carbon atoms, particularly from 2 to 4 carbon atoms, for instance 2 or 3 carbon atoms, advantageously 2 carbon atoms.
  • an aqueous composition comprising at least:
  • At least one of, and more frequently only two of R 1 , R 2 , R 3 and R 4 comprises 5 to 15 carbon atoms, for instance 9 to 11 carbon atoms. Conveniently, these chains may be saturated.
  • At least one of the other of the R 1 , R 2 , R 3 and R 4 groups comprises 1 to 3 carbon atoms, in particular 1 carbon atom (i.e. a methyl group). Conveniently, this chain may be saturated.
  • n 1
  • X p- and Y p- are the anions which act as counterpart of the ammonium cation.
  • X p- and Y p- can be selected from any kind of typical anions, including chloride, bromide, and carboxylates, advantageously carboxylates.
  • quaternary ammonium salt corresponding to this certain embodiment is didecyl-methyl-poly(oxyethyl) ammonium carboxylate, preferably N,N-didecyl-N-methyl-poly(oxyethyl) ammonium propionate.
  • the quaternary ammonium may be present in the composition according to the first or second aspect of the present invention or according to the certain embodiment of the present invention, in an amount from 1 to 5 wt%.
  • composition comprising at least:
  • the alcohol ethoxylate may typically be present in the composition according to the third aspect of the present invention in an amount from 0.5 to 5 wt%.
  • composition comprising at least:
  • the at least one peracid present into the compositions according to any of the above-mentioned aspects and embodiments of the present invention may typically comprise from 3 to 10 carbon atoms, in particular from 4 to 6 carbon atoms. For instance, it can be a mixture of from C4 to C6 peracids.
  • the peracid may be present in the composition of the present invention in an amount from 0.1 to 7 wt%, in particular from 1 to 5 wt%, especially from 3 to 5wt%.
  • Said peracid may comprise at least one monopercarboxylic acid and/or at least one ester percarboxylic acid (or ester peracid, i.e. a compound comprising an ester group and a CO 3 H group), such as methylester percarboxylic acid(s).
  • the peracid comprises both at least one monopercarboxylic acid and at least one ester percarboxylic acid.
  • Said monopercarboxylic acid may for instance be present into the composition of the present invention in an amount from 1 to 3 wt%.
  • Said ester percarboxylic acid may for example be present into the composition of the present invention in an amount from 1 to 3 wt%.
  • the composition could also comprise from 1 to 3 wt% of monopercarboxylic acid(s) and from 1 to 3 wt% of ester percarboxylic acid(s).
  • compositions may also be present in the composition according to any previous aspects and embodiments of the invention, and these may include at least one of hydrogen peroxide, dicarboxylic acids, dipercarboxylic acids (that is with two CO 3 H groups), esters, diesters, and ester acids (that is with an ester group and a COOH group).
  • dicarboxylic acids that is with two CO 3 H groups
  • esters that is with two CO 3 H groups
  • ester acids that is with an ester group and a COOH group
  • the carbon chains lengths are in the range of from 3 to 10 carbon atoms, especially from 4 to 6 carbon atoms, for instance a mixture of from C4 to C6 chain lengths.
  • composition according to any aspects or embodiments of the present invention may comprise the reaction mixture of an acid or an ester, especially an ester acid (i.e. a compound comprising an ester group and a COOH group) or a diester, and hydrogen peroxide.
  • an ester acid i.e. a compound comprising an ester group and a COOH group
  • a diester i.e. a compound comprising an ester group and a COOH group
  • hydrogen peroxide i.e. a compound comprising an ester group and a COOH group
  • the composition of the present invention comprises the composition sold by Solvay SA under the brand name Perestane TM .
  • the present invention also provides a use of a composition as described herein as a biocide, usually after dilution in water.
  • Example 1 (samples A1, B1 and C1)
  • Perestane TM is a mixture including C4 to C6 dicarboxylic acids, monocarboxylic percarboxylic acids , di-percarboxylic acids, monoester percarboxylic acids (or ester peracids), ester acids, diesters and hydrogen peroxide.
  • Perestane TM is available from Solvay SA.
  • the samples were:
  • Table 1 Results expressed as %w/w peracid Days after mixing Sample A1 Perestane TM & water Sample B1 Perestane TM & benzalkonium chloride Sample C1 Perestane TM & Bardap-26 TM 3 4 2.2 4 9 4.1 1.6 4 16 4.2 1.2 4 41 4 4.1 91 4.2 4.5
  • Table 2 Results expressed as % available oxygen (AvOx) Days after mixing Sample A1 Perestane TM & water Sample B1 Perestane TM & benzalkonium chloride Sample C1 Perestane TM & Bardap-26 TM 3 6.1 5.1 6.2 9 6.3 3.0 6.2 16 6.2 6.2 41 6.2 6.1 91 6.2 6.1
  • sample A1 (comprising water) is stable, showing no loss of peracid or of available oxygen.
  • Perestane TM is combined with a known quat, such as benzalkonium chloride (sample B1), the stability is lost: a strong decrease of the peracids concentration and an almost total loss of available oxygen are observed after 16 days.
  • Example 2 (samples A2, B2 and C2)
  • Neodol TM 91-8 provides a stable composition, as measured by peracid content and available oxygen (AvOx) over time.
  • the stability of the peracid composition is maintained in the control experiment, with water.
  • the stability is lost: after 91 days, the content in peracid and the available oxygen are significantly reduced.
  • Neodol TM 91/8 in accordance with the present invention the stability of the peracid composition was maintained.
EP10169207A 2010-07-12 2010-07-12 Composition de peroxygène Withdrawn EP2407529A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP10169207A EP2407529A1 (fr) 2010-07-12 2010-07-12 Composition de peroxygène
PCT/EP2011/061601 WO2012007377A2 (fr) 2010-07-12 2011-07-08 Composition de peroxygène

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP10169207A EP2407529A1 (fr) 2010-07-12 2010-07-12 Composition de peroxygène

Publications (1)

Publication Number Publication Date
EP2407529A1 true EP2407529A1 (fr) 2012-01-18

Family

ID=43127451

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10169207A Withdrawn EP2407529A1 (fr) 2010-07-12 2010-07-12 Composition de peroxygène

Country Status (2)

Country Link
EP (1) EP2407529A1 (fr)
WO (1) WO2012007377A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2724614A1 (fr) * 2012-10-24 2014-04-30 Wesso Ag Utilisation d'une composition de nettoyage notamment pour la désinfection et/ou la réduction des germes des oeufs et procédé

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102011113233A1 (de) 2011-09-06 2013-03-07 Guanglai Xu Ein neues Verfahren zum Laden und Entladen einer Kondensator-Block-Kette für elektrische Energiespeicherung

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994000548A1 (fr) * 1992-06-19 1994-01-06 Laporte E.S.D. Limited Compositions contenant un peracide organique et un compose d'ammonium quaternaire
EP1192860A1 (fr) * 2000-09-29 2002-04-03 Air Liquide Santé (International) Désinfectant conténant un traceur-UVA et méthode pour déterminer la dilution des désinfectants avec les traceurs-UVA
US20020128164A1 (en) * 2000-11-30 2002-09-12 Tosoh Corporation Resist stripper
US20020192340A1 (en) 2001-02-01 2002-12-19 Swart Sally Kay Method and system for reducing microbial burden on a food product
US20030109403A1 (en) 2001-06-05 2003-06-12 Ecolab, Inc. Solid cleaning composition including stabilized active oxygen component

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9412051D0 (en) 1994-06-16 1994-08-03 Solvay Interox Ltd Novel peroxygen compounds
GB9626637D0 (en) 1996-12-21 1997-02-12 Solvay Interox Ltd Percarboxyilic acid solutions
EP0967203A1 (fr) 1998-06-22 1999-12-29 SOLVAY (Société Anonyme) Procédé pour la préparation d'une solution aqueuse d'un monoester d'acide peroxycarboxylique, la solution obtenue par ce procédé, et son utilisation comme désinfectant
US7060301B2 (en) * 2001-07-13 2006-06-13 Ecolab Inc. In situ mono-or diester dicarboxylate compositions
US6627593B2 (en) * 2001-07-13 2003-09-30 Ecolab Inc. High concentration monoester peroxy dicarboxylic acid compositions, use solutions, and methods employing them

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994000548A1 (fr) * 1992-06-19 1994-01-06 Laporte E.S.D. Limited Compositions contenant un peracide organique et un compose d'ammonium quaternaire
EP1192860A1 (fr) * 2000-09-29 2002-04-03 Air Liquide Santé (International) Désinfectant conténant un traceur-UVA et méthode pour déterminer la dilution des désinfectants avec les traceurs-UVA
US20020128164A1 (en) * 2000-11-30 2002-09-12 Tosoh Corporation Resist stripper
US20020192340A1 (en) 2001-02-01 2002-12-19 Swart Sally Kay Method and system for reducing microbial burden on a food product
US20030109403A1 (en) 2001-06-05 2003-06-12 Ecolab, Inc. Solid cleaning composition including stabilized active oxygen component

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2724614A1 (fr) * 2012-10-24 2014-04-30 Wesso Ag Utilisation d'une composition de nettoyage notamment pour la désinfection et/ou la réduction des germes des oeufs et procédé

Also Published As

Publication number Publication date
WO2012007377A2 (fr) 2012-01-19
WO2012007377A3 (fr) 2012-03-22

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