WO2000072890A1 - Aqueous odor absorbing composition - Google Patents

Aqueous odor absorbing composition Download PDF

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Publication number
WO2000072890A1
WO2000072890A1 PCT/CH2000/000280 CH0000280W WO0072890A1 WO 2000072890 A1 WO2000072890 A1 WO 2000072890A1 CH 0000280 W CH0000280 W CH 0000280W WO 0072890 A1 WO0072890 A1 WO 0072890A1
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WO
WIPO (PCT)
Prior art keywords
acid
composition
composition according
carboxylic
weight
Prior art date
Application number
PCT/CH2000/000280
Other languages
French (fr)
Inventor
Christian Quellet
Sandrine Dumas
Original Assignee
Givaudan 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 Givaudan Sa filed Critical Givaudan Sa
Priority to JP2000620996A priority Critical patent/JP2003500173A/en
Priority to EP00925012A priority patent/EP1100551A1/en
Publication of WO2000072890A1 publication Critical patent/WO2000072890A1/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00Disinfection, sterilisation or deodorisation of air
    • A61L9/14Disinfection, sterilisation or deodorisation of air using sprayed or atomised substances including air-liquid contact processes
    • A61L9/145Disinfection, sterilisation or deodorisation of air using sprayed or atomised substances including air-liquid contact processes air-liquid contact processes, e.g. scrubbing
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00Disinfection, sterilisation or deodorisation of air
    • A61L9/01Deodorant compositions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2209/00Aspects relating to disinfection, sterilisation or deodorisation of air
    • A61L2209/20Method-related aspects
    • A61L2209/22Treatment by sorption, e.g. absorption, adsorption, chemisorption, scrubbing, wet cleaning

Definitions

  • the present invention relates to an aqueous odor absorbing composition for use in the air and on surfaces except for use directly on humans.
  • compositions are used to control odor especially malodor.
  • Such compositions comprise perfumes, colognes, active compounds which react with malodor, compounds comprising antibacterial and antifungal agents etc.
  • WO96/04937 discloses an odor control composition consisting of an aqueous solution comprising '. ater-soluble cyclocextnns, antimicrobial preservatives and optionally a perfume.
  • the cyclodextrins used are alpha-, beta- and gamma- cyclodextrins consisting of glucose units arranged in a donut-shaped ring which forms inclusion complexes with organic molecules e.g. those of malodors.
  • Betacyclodextrin is preferred for aiodor-absorption due to its ring size and low cost, however, having a solubility limit of about 1.85 % at room temperature it can only be used in a concentration of up to this limit. For desirable higher concentration betacyclodextrin is derivatised. In such derivatives some of the OH-groups of beta-cyclodextrir. are converted to OR-groups. Tr.e known compositions are used for malodor- absorpt on or -control on textiles by spraying.
  • the US-A-5 6?7 854, US-A-5 879 66 and US-A-5 534 165 also descnoe the use of clo ⁇ extnns for odor absorption.
  • Beta-cyclodextrin s used in all cases either m a concentration up to ts solubility limit of 1.85% cr, f higher concentration is desired, in a derivatised form.
  • the solutions of the above documents comprise also antimicrobial preservatives. The solubility of the latter is improved, if desired, by the addition of small amounts of 0.001 to 0.3% of a chelating agent.
  • One object of the present invention is to provide a novel malodor-absorbing composition having a high malodor-control .
  • a further object of the present invention is to provide an aqueous malodor-absorbing composition with a low level of olfactive compounds.
  • a further object of the present invention is to provide an aqueous malodor absorbing composition with a high concentration of beta-cyclodextrin.
  • a further object of the present invention is to provide an aqueous malodor-absorbing composition with a low viscosity and therefore with good spraying quality.
  • the present invention refers to an aqueous odor absorbing composition comprising a cyclodextrin and an antimicrobial preservative characterized by
  • Carboxylic acids which enhance the solubility of beta- cyclodextrin are carboxylic monoacids and polyacids which may be substituted by one or more hydroxy groups such as glycolic acid, lactic acid, malonic acid, malic acid, glutaric acid, diglycolic acid, succinic acid, citramalic acid, tartaric acid, mucic acid, adipic acid and derivatives thereof.
  • the preferred carboxylic acids are hydroxy-carboxylic polyacids such as citric acid, which may be present in an amount of 1 to 8 % preferably in an amount of 6 % per weight of the total composition.
  • carboxylic acid compositions according to the present invention may comprise up to 14 % of beta- cylcodextrins, amounts of 1.85 to 10 % give good results and amounts of 1.9 to 6 % are preferred.
  • Antimicrobial preservatives are useful for stabilizing the composition of the invention.
  • Preferred antimicrobial water soluble preservatives are paraben, phenyl and phenoxy compounds such as phenyl ethanol, phenoxyethanol, organic nitrogen compounds such as imidazolidinyl urea, organic sulfur compounds such as 5-chloro-2-methyl-4-isothiazolin-3-one and 2- methyl-4-isothiazolin-3-one, halogenated compounds such as chlorobutanol, trichlorohydroxy-diphenylether, parachlorometa-cresol, metallic salts such as copper salts and zinc salts e.g. ZnCl 2 .
  • the amount of beta-cyclodextrin disolved in the compositions of the present invention alone is sufficient to control malodor in an appreciable extent, however, olfactive compounds can be added to impart pleasant odors to a substrate the composition is applied to. Small amounts of olfactive compounds give surprisingly good results i.e. additionally improving control of malodor and adding a pleasant odor at the use of the compositions of the present invention.
  • solubilizing agents for the olfactive compounds such as fragrances
  • Such solubilizing agents are nonionic, anionic, cationic and amphoteric surfactants.
  • Nonionic surfactants are block copolymers, graft copolymers and homopolymers all being more hydrophylic than hydrophobic.
  • Preferred anionic surfactants are alkyl sulfonate.
  • Such solubilizing agents may be present in an amount of 0.01 to 5 % preferably 0.01 to 4 %.
  • compositions of the invention may be used to control odor especially malodor in the environment (air-freshener) and on any structured surface such as textiles, rugs, walls etc.
  • air-freshener any structured surface such as textiles, rugs, walls etc.
  • in liquid form they may be sprayed or if containing a thickener and thus having a higher viscosity applied with conventional means such as a paintbrush.
  • Perfume is a composition of the following 15 compounds: amylacetate, eucalyptol, dymethyloctenon, Cyclal C, linalool, Aldehyde C12 MNA, viridine, terpineol, benzylacetat, irisone, verdylaceta , phenyl ethyl alcohol, diphenyloxid, prunolide, lilial.
  • Perfume 2* is a composition of the following 15 compounds: limonen, tetrahydrolinalool, dihydromyrcenol, anethol, citronellol, alpha-methyl ionone, phenyl ethyl alcohol, lilial, ⁇ -nonalacton, vertofix, ⁇ -decalactone, methyldihydrojasmonale, cumarin, verdyl-propionate, verdylacetat .
  • the malodor control or coverage is evaluated directly in the gas phase against tobacco and kitchen malodors by a panel of 4 trained individuals.
  • the panelist evaluate systems with different beta-cyclodextrin concentrations of Examples 1-11 at a constant concentration of malodor. The results are shown in Table III. The best malodor control is denoted by 3.
  • the malodor control is evaluated in situ by a group of 10 trained individuals.
  • the compositions are sprayed on a fabric with tobacco malodor. Fabrics sprayed with the compositions and unsprayed fabrics are compared. The results are shown in Table IV. Table IV

Abstract

The invention relates to an aqueous odor absorbing composition comprising 1.8 - 14 % per weight betacyclodextrin, 0.1 - 11 % by weight of a water soluble carboxylic acid and 0.1 - 0.3 % per weight of an antimicrobial preservative. The aqueous odor absorbing composition of the invention may be used in the air or any surface with the exception of humans.

Description

Aqueous Odor Absorbing Composition
The present invention relates to an aqueous odor absorbing composition for use in the air and on surfaces except for use directly on humans.
A wide variety of compositions are used to control odor especially malodor. Such compositions comprise perfumes, colognes, active compounds which react with malodor, compounds comprising antibacterial and antifungal agents etc. WO96/04937 discloses an odor control composition consisting of an aqueous solution comprising '. ater-soluble cyclocextnns, antimicrobial preservatives and optionally a perfume. The cyclodextrins used are alpha-, beta- and gamma- cyclodextrins consisting of glucose units arranged in a donut-shaped ring which forms inclusion complexes with organic molecules e.g. those of malodors. Betacyclodextrin is preferred for aiodor-absorption due to its ring size and low cost, however, having a solubility limit of about 1.85 % at room temperature it can only be used in a concentration of up to this limit. For desirable higher concentration betacyclodextrin is derivatised. In such derivatives some of the OH-groups of beta-cyclodextrir. are converted to OR-groups. Tr.e known compositions are used for malodor- absorpt on or -control on textiles by spraying.
The US-A-5 6?7 854, US-A-5 879 66 and US-A-5 534 165 also descnoe the use of
Figure imgf000002_0001
cloαextnns for odor absorption. Beta-cyclodextrin s used in all cases either m a concentration up to ts solubility limit of 1.85% cr, f higher concentration is desired, in a derivatised form. The solutions of the above documents comprise also antimicrobial preservatives. The solubility of the latter is improved, if desired, by the addition of small amounts of 0.001 to 0.3% of a chelating agent.
One object of the present invention is to provide a novel malodor-absorbing composition having a high malodor-control .
A further object of the present invention is to provide an aqueous malodor-absorbing composition with a low level of olfactive compounds.
A further object of the present invention is to provide an aqueous malodor absorbing composition with a high concentration of beta-cyclodextrin.
A further object of the present invention is to provide an aqueous malodor-absorbing composition with a low viscosity and therefore with good spraying quality.
It has been surprisingly found that addition of carboxylic acids to an aqueous solution multiplies the solubility of non-derivatised beta-cyclodextrin.
Therefore, the present invention refers to an aqueous odor absorbing composition comprising a cyclodextrin and an antimicrobial preservative characterized by
1.8 to 14 % by weight of the total composition of beta-cyclodextrin
0.1 to 11 % by weight of the total composition of a water-soluble carboxylic acid and 0.1 to 0.3 % by weight of the total composition of the antimicrobial preservative,
whereby all three components are in solution.
Carboxylic acids which enhance the solubility of beta- cyclodextrin are carboxylic monoacids and polyacids which may be substituted by one or more hydroxy groups such as glycolic acid, lactic acid, malonic acid, malic acid, glutaric acid, diglycolic acid, succinic acid, citramalic acid, tartaric acid, mucic acid, adipic acid and derivatives thereof. The preferred carboxylic acids are hydroxy-carboxylic polyacids such as citric acid, which may be present in an amount of 1 to 8 % preferably in an amount of 6 % per weight of the total composition.
Due to the surprising solubilizing effect of the carboxylic acid compositions according to the present invention may comprise up to 14 % of beta- cylcodextrins, amounts of 1.85 to 10 % give good results and amounts of 1.9 to 6 % are preferred.
Antimicrobial preservatives are useful for stabilizing the composition of the invention.
Preferred antimicrobial water soluble preservatives are paraben, phenyl and phenoxy compounds such as phenyl ethanol, phenoxyethanol, organic nitrogen compounds such as imidazolidinyl urea, organic sulfur compounds such as 5-chloro-2-methyl-4-isothiazolin-3-one and 2- methyl-4-isothiazolin-3-one, halogenated compounds such as chlorobutanol, trichlorohydroxy-diphenylether, parachlorometa-cresol, metallic salts such as copper salts and zinc salts e.g. ZnCl2.
The amount of beta-cyclodextrin disolved in the compositions of the present invention alone is sufficient to control malodor in an appreciable extent, however, olfactive compounds can be added to impart pleasant odors to a substrate the composition is applied to. Small amounts of olfactive compounds give surprisingly good results i.e. additionally improving control of malodor and adding a pleasant odor at the use of the compositions of the present invention.
Further solubilizing agents for the olfactive compounds, such as fragrances, may be added. Such solubilizing agents are nonionic, anionic, cationic and amphoteric surfactants. Nonionic surfactants are block copolymers, graft copolymers and homopolymers all being more hydrophylic than hydrophobic. Preferred anionic surfactants are alkyl sulfonate. Such solubilizing agents may be present in an amount of 0.01 to 5 % preferably 0.01 to 4 %.
The compositions of the invention may be used to control odor especially malodor in the environment (air-freshener) and on any structured surface such as textiles, rugs, walls etc. In liquid form they may be sprayed or if containing a thickener and thus having a higher viscosity applied with conventional means such as a paintbrush.
The invention is further described in the examples. Examples 1 to 11
The ingredients given in Table I and II are r.ixed and dissolved to form a clear solution.
Table I
Figure imgf000006_0001
Perfume is a composition of the following 15 compounds: amylacetate, eucalyptol, dymethyloctenon, Cyclal C, linalool, Aldehyde C12 MNA, viridine, terpineol, benzylacetat, irisone, verdylaceta , phenyl ethyl alcohol, diphenyloxid, prunolide, lilial.
Table II
Figure imgf000006_0002
Perfume 2* is a composition of the following 15 compounds: limonen, tetrahydrolinalool, dihydromyrcenol, anethol, citronellol, alpha-methyl ionone, phenyl ethyl alcohol, lilial, γ-nonalacton, vertofix, γ-decalactone, methyldihydrojasmonale, cumarin, verdyl-propionate, verdylacetat .
In a first set of evaluation the malodor control or coverage is evaluated directly in the gas phase against tobacco and kitchen malodors by a panel of 4 trained individuals. The panelist evaluate systems with different beta-cyclodextrin concentrations of Examples 1-11 at a constant concentration of malodor. The results are shown in Table III. The best malodor control is denoted by 3.
Table III
Figure imgf000007_0001
In a second set of evaluation the malodor control is evaluated in situ by a group of 10 trained individuals. The compositions are sprayed on a fabric with tobacco malodor. Fabrics sprayed with the compositions and unsprayed fabrics are compared. The results are shown in Table IV. Table IV
Figure imgf000008_0001

Claims

Claims
1. An aqueous odor absorbing composition comprising a cyclodextrin and an antimicrobial preservative characterized by
1.8 to 14 % by weight of the total composition of beta-cyclodextrin
0.1 to 11 % by weight of the total composition of a water-soluble carboxylic acid and
0.1 to 0.3 % by weight of the total composition of the antimicrobial preservative,
whereby all three components are in solution.
2. Composition according to claim 1 wherein the carboxylic acid is a carboxylic monoacid which may be substituted by a hydroxy group.
3. Composition according to claim 1 wherein the carboxylic acid is a carboxylic polyacid which may be substituted by one or more hydroxy groups.
4. Composition according to claim 1 wherein the carboxylic acid is selected from a group consisting of glycolic acid, lactic acid, malonic acid, malic acid, glutaric acid, diglycolic acid, succinic acid, citramalic acid, tartaric acid, mucic acid, adipic acid and polyacrylic acid or derivatives thereof.
5. Composition according to claim 3 wherein the carboxylic polyacid is citric acid in an amount of 1 to 8 % per weight of the total composition.
6. Composition according to one of the preceding claims comprising 1.85 to 10 % per weight of the total composition of beta-cyclodextrin.
7. Composition according to claim 6 comprising 1.9 to 6 % per weight of beta-cyclodextrin.
8. Composition according to any of the preceding claims comprising 0.001 to 1 % per weight of the total composition of a fragrance or fragrance composition.
9. Composition according to any of the preceding claims comprising 0.01 to 5 % per weight of the total composition of a solubilizing agent for the fragrance or fragrance composition.
10. Composition according to claim 1 comprising 0.0002 to 0.2 % per weight of the total composition of the antimicrobial preservative.
11. Composition according to anyone of the preceding claims in liquid form.
12. Composition according to claim 13 in form of a spray.
13. Composition according to any of the preceding claims comprising a thickening agent.
PCT/CH2000/000280 1999-05-31 2000-05-19 Aqueous odor absorbing composition WO2000072890A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2000620996A JP2003500173A (en) 1999-05-31 2000-05-19 Odor absorbing aqueous composition
EP00925012A EP1100551A1 (en) 1999-05-31 2000-05-19 Aqueous odor absorbing composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP99810470.7 1999-05-31
EP99810470 1999-05-31

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WO2000072890A1 true WO2000072890A1 (en) 2000-12-07

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013148716A3 (en) * 2012-03-30 2013-12-27 Robertet, Inc. Malodor neutralizing compositions containing acids and alicyclic ketones
US8741275B2 (en) 2010-06-04 2014-06-03 Robetet, Inc. Malodor neutralizing compositions comprising undecylenic acid or citric acid
US9200241B2 (en) 2011-01-27 2015-12-01 Robertet, Inc. Malodor neutralizing compositions comprising bornyl acetate or isobornyl acetate

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4758654B2 (en) * 2005-01-26 2011-08-31 株式会社ソフト99コーポレーション Deodorization method
JP4782478B2 (en) * 2005-06-07 2011-09-28 花王株式会社 Fragrance composition

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63315200A (en) * 1987-06-15 1988-12-22 Jiyoriibu:Kk Deodorizer for cattle feces and urine
JPH0841780A (en) * 1994-07-26 1996-02-13 Nikka Chem Co Ltd Rinsing supplement composition for washing
WO1996004937A1 (en) * 1994-08-12 1996-02-22 The Procter & Gamble Company Uncomplexed cyclodextrin solutions for odor control on inanimate surfaces
US5534165A (en) * 1994-08-12 1996-07-09 The Procter & Gamble Company Fabric treating composition containing beta-cyclodextrin and essentially free of perfume
US5879666A (en) * 1996-10-24 1999-03-09 The Procter & Gamble Company Methods and compositions for reducing body odor
US5897854A (en) * 1997-06-09 1999-04-27 The Procter & Gamble Company Methods for reducing body odor

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63315200A (en) * 1987-06-15 1988-12-22 Jiyoriibu:Kk Deodorizer for cattle feces and urine
JPH0841780A (en) * 1994-07-26 1996-02-13 Nikka Chem Co Ltd Rinsing supplement composition for washing
WO1996004937A1 (en) * 1994-08-12 1996-02-22 The Procter & Gamble Company Uncomplexed cyclodextrin solutions for odor control on inanimate surfaces
US5534165A (en) * 1994-08-12 1996-07-09 The Procter & Gamble Company Fabric treating composition containing beta-cyclodextrin and essentially free of perfume
US5879666A (en) * 1996-10-24 1999-03-09 The Procter & Gamble Company Methods and compositions for reducing body odor
US5897854A (en) * 1997-06-09 1999-04-27 The Procter & Gamble Company Methods for reducing body odor

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 198906, Derwent World Patents Index; Class D15, AN 1989-043082, XP002121540 *
DATABASE WPI Section Ch Week 199616, Derwent World Patents Index; Class D25, AN 1996-157617, XP002121541 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8741275B2 (en) 2010-06-04 2014-06-03 Robetet, Inc. Malodor neutralizing compositions comprising undecylenic acid or citric acid
US9200241B2 (en) 2011-01-27 2015-12-01 Robertet, Inc. Malodor neutralizing compositions comprising bornyl acetate or isobornyl acetate
WO2013148716A3 (en) * 2012-03-30 2013-12-27 Robertet, Inc. Malodor neutralizing compositions containing acids and alicyclic ketones
US9114180B2 (en) 2012-03-30 2015-08-25 Robertet, Inc. Malodor neutralizing compositions containing acids and alicyclic ketones
EP3056247A3 (en) * 2012-03-30 2016-10-12 Robertet, Inc. Malodor neutralizing compositions containing acids and alicyclic ketones
EP3056247B1 (en) 2012-03-30 2018-06-13 Robertet, Inc. Malodor neutralizing compositions containing citric acid and alicyclic ketones

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Publication number Publication date
JP2003500173A (en) 2003-01-07
EP1100551A1 (en) 2001-05-23

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