WO2019130207A1 - Compositions de neutralisation des mauvaises odeurs et leurs procédés d'utilisation - Google Patents
Compositions de neutralisation des mauvaises odeurs et leurs procédés d'utilisation Download PDFInfo
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- WO2019130207A1 WO2019130207A1 PCT/IB2018/060571 IB2018060571W WO2019130207A1 WO 2019130207 A1 WO2019130207 A1 WO 2019130207A1 IB 2018060571 W IB2018060571 W IB 2018060571W WO 2019130207 A1 WO2019130207 A1 WO 2019130207A1
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- WIPO (PCT)
- Prior art keywords
- laundry
- ppm
- benzyl
- tetrahydropyran
- composition
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 17
- RLYSPFPWKAALMR-UHFFFAOYSA-N 3-benzyloxane Chemical compound C=1C=CC=CC=1CC1CCCOC1 RLYSPFPWKAALMR-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000007788 liquid Substances 0.000 claims abstract description 18
- 230000000873 masking effect Effects 0.000 claims abstract description 10
- 239000002979 fabric softener Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 4
- 239000002736 nonionic surfactant Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 230000001580 bacterial effect Effects 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 239000004745 nonwoven fabric Substances 0.000 claims 1
- 239000012209 synthetic fiber Substances 0.000 claims 1
- 229920002994 synthetic fiber Polymers 0.000 claims 1
- 229920003002 synthetic resin Polymers 0.000 claims 1
- 239000000057 synthetic resin Substances 0.000 claims 1
- 239000002759 woven fabric Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 14
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 14
- 239000004744 fabric Substances 0.000 description 13
- BSAIUMLZVGUGKX-UHFFFAOYSA-N non-2-enal Chemical compound CCCCCCC=CC=O BSAIUMLZVGUGKX-UHFFFAOYSA-N 0.000 description 12
- 239000002304 perfume Substances 0.000 description 12
- 241001478294 Moraxella osloensis Species 0.000 description 10
- 241000191967 Staphylococcus aureus Species 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 230000001953 sensory effect Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 7
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 6
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003205 fragrance Substances 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 238000010412 laundry washing Methods 0.000 description 6
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002781 deodorant agent Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 210000004243 sweat Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000006285 cell suspension Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 3
- WRYLYDPHFGVWKC-UHFFFAOYSA-N 4-terpineol Chemical compound CC(C)C1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000035985 Body Odor Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010040904 Skin odour abnormal Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 230000001877 deodorizing effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- -1 gums Substances 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 210000002374 sebum Anatomy 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 235000019832 sodium triphosphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- PMXWKVSABVAGCT-UHFFFAOYSA-N 3-benzyloxolane Chemical compound C=1C=CC=CC=1CC1CCOC1 PMXWKVSABVAGCT-UHFFFAOYSA-N 0.000 description 1
- WRYLYDPHFGVWKC-SNVBAGLBSA-N 4-Terpineol Natural products CC(C)[C@]1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-SNVBAGLBSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- 208000008454 Hyperhidrosis Diseases 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 229920002774 Maltodextrin Polymers 0.000 description 1
- 241000588621 Moraxella Species 0.000 description 1
- 244000299790 Rheum rhabarbarum Species 0.000 description 1
- 235000009411 Rheum rhabarbarum Nutrition 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000001111 citrus aurantium l. leaf oil Substances 0.000 description 1
- 239000010634 clove oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000013460 sweaty Diseases 0.000 description 1
- 239000010677 tea tree oil Substances 0.000 description 1
- 229940111630 tea tree oil Drugs 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- FRPJTGXMTIIFIT-UHFFFAOYSA-N tetraacetylethylenediamine Chemical compound CC(=O)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O FRPJTGXMTIIFIT-UHFFFAOYSA-N 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0068—Deodorant compositions
-
- 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
- C11D3/0015—Softening compositions liquid
-
- 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
- C11D3/2096—Heterocyclic 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
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- 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
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/12—Soft surfaces, e.g. textile
Definitions
- the present invention relates generally to malodor counteracting compositions, and more particularly to compositions including 3-benzyl-tetrahydropyran, which are capable of masking or counteracting malodors arising from odor-causing bacteria, such as Moraxella osloensis (Gram negative) and Staphylococcus aureus (Gram positive).
- odor-causing bacteria such as Moraxella osloensis (Gram negative) and Staphylococcus aureus (Gram positive).
- Fabric products brought into direct contact with human skin including underclothes, towels, handkerchiefs and the like, have a potential to absorb or attach sweat containing sebum, corneous substances and the like.
- These fabric products have a propensity to produce a “wet-and-dirty-dustcloth-malodor” or an “acidic or sweaty odor” characteristic once they are damp.
- This phenomena has been observed where after washing, the laundered fabric products are left untouched in a damp place such as the inside of a laundering machine tub for a long time, or if insufficiently dried.
- the malodor readily appears once the product has been wetted with rain or sweat. This malodor is generally called a“damp-dry malodor.”
- the damp-dry malodor of some previously laundered fabric products can be temporarily eliminated by sufficiently drying the fabric products after laundry.
- the damp-dry malodor may reoccur at the time of use or when the fabric products become damp (e.g., from sweat, rain or the like). This can even occur from dry, laundered fabric products from which no damp-dry malodor is sensed.
- This reoccurring damp-dry malodor may be produced not only in a case where fabric products are dried indoors, but also in a case where a dryer or a washing machine having a low temperature drying function is used, and even in the case of fabric products that have been dried outdoors, if the fabric products become damp.
- the reoccurring damp-dry malodor can also appear when fabric products are stored in a wardrobe or the like for a long time.
- Patent 1 Prior work reported in JP5767831 (B2) (Patent 1 ) and Kubota et al.“Moraxella Species Are Primarily responsible for Generating Malodor in Laundry,” Appl. Environ. Microbiol., 2012, 73:3317-3324, reveal that microorganisms such as Moraxella osloensis, as well as Staphylococcus aureus in combination with sebum, sweat, or soil in laundry, which remain even after washing, give rise to compounds that create the damp-dry malodor. Accordingly, Patent 1 discloses that inhibiting or eliminating these microorganisms with a spray-on alcohol solution comprising various damp-dry odor control agents possessing ketone, lactone, or ester functionality is one way of combating this problem.
- the present invention is premised on the realization that an effective concentration of 3-benzyl-tetrahydropyran in a medium is capable of deodorizing, inhibiting, or eliminating a damp-dry malodor in a substrate.
- a method for counteracting or masking malodor in laundry articles comprises providing a laundry composition comprising 3-benzyl-tetrahydropyran; combining the laundry composition with a liquid medium for contacting the laundry articles, and contacting the laundry articles with the liquid medium comprising the laundry composition.
- the concentration of 3-benzyl-tetrahydropyran in the liquid medium is at least 15 ppm based on the total mass of the laundry composition.
- a laundry composition for counteracting or masking malodor in laundry articles comprises 3-benzyl-tetrahydropyran; and a detersive surfactant or a fabric softener active, wherein the detersive surfactant is selected from the group consisting of an anionic surfactant, a non-ionic surfactant, and combinations thereof; and wherein the fabric softener active is selected from the group consisting of a silicon polymer or compound, a cationic ammonium or imidazolinium polymer or compound, and a combination thereof.
- FIG. 1 is a plot of ammonia concentration in headspace of a sample over time for samples with or without 3-benzyl-tetrahydropyran;
- FIG. 2 is a plot of trimethylamine concentration in headspace of a sample over time for samples with or without 3-benzyl-tetrahydropyran;
- FIG. 3 is a plot of methyl mercaptan concentration in headspace of a sample over time for samples with or without 3-benzyl-tetrahydropyran;
- FIG. 4 is a plot of diacetyl concentration in headspace of a sample over time for samples with or without 3-benzyl-tetrahydropyran;
- FIGS. 5A and 5B are plots of sensory scores for a 10 ppm (w/w) isovaleric acid sample and a 5 ppm nonenal sample, respectively, with 0.0x, 0.5x, 1 .0x, 2.0x, and 3. Ox ppm of 3-benzyl-tetrahydropyran; and
- FIGS. 6A and 6B are plots of gas chromatography analysis of isovaleric acid and nonenal concentration in the headspace of the 0.0x and 3.0x samples used in FIGS. 5A and 5B, respectively.
- the present invention relates in general to the field of fragrances, and more particularly to malodor counteracting compositions including 3-benzyl-tetrahydropyran, which are capable of masking or counteracting malodors arising from odor-causing bacteria, such as Moraxella osloensis (Gram negative) and Staphylococcus aureus (Gram positive).
- a laundry composition for counteracting or masking malodor in laundry articles is provided.
- the composition comprises 3-benzyl-tetrahydropyran formulated in a laundry product, such as laundry washing powders, laundry washing liquids, or fabric softener compositions.
- the malodor counteracting agent of the present invention i.e. , 3-benzyl-tetrahydropyran
- 3-benzyl-tetrahydropyran is fragrant, and is described as geranium, woody, phenolic, lactonic, and having a natural rhubarb note with a green astringent woody aspect, suitable for use in a fragrance composition or in perfumery.
- 3-benzyl- tetrahydropyran is marketed under the French registered tradename BETAHYDRANE by V. MANE FILS.
- a method for counteracting or masking malodor in laundry articles comprises providing a laundry composition comprising 3-benzyl-tetrahydropyran; combining the laundry composition with a liquid medium for contacting the laundry articles, and contacting the laundry articles with the liquid medium comprising the laundry composition.
- concentration of 3-benzyl-tetrahydropyran in the liquid medium is at least 15 ppm based on the total mass of the laundry composition.
- laundry product includes laundry washing powders, laundry washing liquids, or fabric softener compositions.
- fragment denotes a compound that gives off an odor.
- perfumery denotes not only perfumery in the usual sense of the term, but also other fields in which the odor of products is important. These may be perfumery compositions in the usual sense of the term, such as fragrancing bases and concentrates, eaux de Cologne, eaux de toilette, fragrances and similar products.
- the amount of the 3-benzyl-tetrahydropyran incorporated into a perfumery composition will vary according to the nature of the composition, the desired fragrant effect, and the nature of the other fragrant or non-fragrant compounds that may be present, as well as the washing and rinsing and may be readily determined by a person skilled in the art, given that it may vary within a very wide range, from 0.1 % to 99% by weight, in particular 0.1% to 50% by weight and especially 0.1 % to 30% by weight.
- 3-benzyl-tetrahydropyran may be used as sole fragrant agent or, as is common in perfumery, it may be in a mixture with one or more other fragrant compounds, that a person skilled in the art is capable of selecting as a function of the desired effect.
- the additional fragrant agent(s) may be other fragrant agents known to those skilled in the art.
- Exemplary fragrants include, but are not limited to, hydrocarbon perfume, alcohol perfume, ether perfume, aldehyde perfume, ketone perfume, ester perfume, lactone perfume, or cyclic ketone perfume, etc.
- the content of the 3-benzyl-tetrahydropyran-containing perfume ingredient in the laundry composition is not particularly limited, and is preferably from 0.01 % to 10% by mass, more preferably from 0.01 % to 5.0% by mass, particularly preferably from 0.02% to 2.0% by mass.
- the 3-benzyl-tetrahydropyran-containing perfumery composition may be used neat or it may be incorporated into or onto an inert support material or a material that may contain other active ingredients of the finished composition.
- support materials including, for example, polar solvents, oils, greases, finely divided solids, cyclodextrins, maltodextrins, gums, resins and any other support material known for such compositions.
- the 3-benzyl-tetrahydropyran-containing perfumery composition may be encapsulated.
- Laundry washing powders generally comprise 5-30% by weight of anionic surfactants e.g. alkylbenzenesulphonates, fatty acid soaps, alcohol sulphates or alpha- olefin sulphonates; 1 -10% of non-ionic surfactants such as polyethoxylated alcohols; 0- 5% of lather boosters such as alkanolamides; 35-60% of inorganic builders/fillers such as sodium tripolyphosphate, zeolites, sodium carbonate, sodium sulphate or sodium silicate; 0-15% of bleaching agents such as sodium perborate and bleach precursors such as tetraacetylethylenediamine; up to 15% of additional adjuncts such as optical brightening agents, chelating agents, anti-redeposition agents, enzymes, dyes and perfume; and 2-15% of water.
- anionic surfactants e.g. alkylbenzenesulphonates, fatty acid soaps, alcohol sulphates or alpha
- Laundry washing liquids generally comprise 5-40% by weight of anionic surfactants, e.g. fatty acid soaps or alkylbenzenesulphonates; 1 -20% of non-ionic surfactants, e.g. (poly)ethoxylated alcohols and alkanolamides; 0-30% of builders/sequestrants, e.g. sodium tripolyphosphate, tetrapotassium pyrophosphate, soda ash and silicates; 0-15% of alcohols/coupling agents, e.g. ethanol, glycerol and sodium xylenesulphonate; 1 -5% of additional adjuncts such as anti-redeposition agents, optical brighteners, enzymes, fabric conditioning agents, dyes and perfume; and 40-
- anionic surfactants e.g. fatty acid soaps or alkylbenzenesulphonates
- non-ionic surfactants e.g. (poly)ethoxylated alcohols and alkan
- Fabric conditioners generally comprise 4-50% by weight of cationic actives e.g. quaternary ammonium or imidazoline derivatives, and additionally 0-5% of other lubricants such as lanolin or fatty acids; 0.5-5% of additional adjuncts such as preservatives, dyes, pH control agents, co-solvents, opacifiers, electrolytes and perfume; 49.5-95.5% of water.
- cationic actives e.g. quaternary ammonium or imidazoline derivatives, and additionally 0-5% of other lubricants such as lanolin or fatty acids; 0.5-5% of additional adjuncts such as preservatives, dyes, pH control agents, co-solvents, opacifiers, electrolytes and perfume; 49.5-95.5% of water.
- 3-benzyl-tetrahydropyran is present in the laundry composition a sufficient quantity that, when diluted with a liquid medium (e.g., water) used for washing or treating the laundry articles, provides a deodorant effect to damp-dry malodor.
- a liquid medium e.g., water
- the laundry composition may include 15 ppm, 20 ppm, 25 ppm, 30 ppm, or more, which is effective toward masking various malodors, including nitrogen-based (e.g., ammonia, trialkylamines such as trimethylamine, indole, nicotine, pyridine) or sulfur-based (e.g., methylmercaptan, hydrogen sulfide, thioglycolate), as well as fatty acid-based (e.g., isovaleric acid, carpylic acid, terpenoid, ester, aldehydes) malodors.
- nitrogen-based e.g., ammonia, trialkylamines such as trimethylamine, indole, nicotine, pyridine
- sulfur-based e.g., methylmercaptan, hydrogen sulfide, thioglycolate
- fatty acid-based e.g., isovaleric acid, carpylic acid, terpenoid, ester,
- the laundry composition used for washing or treating the laundry articles may include 40 ppm, 50 ppm, 75 ppm, 100 ppm, 160 ppm, 200 ppm, 250 ppm, 300 ppm, 320 ppm, 400 ppm, or in a range between any two of the foregoing.
- Such ingredients include, but are not limited to, NOREENALTM (6,8- dimethyl-,(6R)-7-nonenal); beta-ionone (4-(2,6,6-trimethylcyclohex-1 -ene-1 -yl)-but-3- ene-2-one); teatree oil; terpinen-4-ol; thymol; cinnamon leaf oil; petitgrain oil; clove oil; patchouli oil; or combinations thereof.
- other factors such as temperature, pH, identity and concentration of surfactants, etc. can also affect MIC values under the present conditions.
- a combination of 3-benzyl- tetrahydropyran and a quaternary ammonium and/or imidazoline derivative softening agent provides enhancement of MIC values.
- the laundry composition used for washing or treating the laundry articles may include an effective concentration of 3-benzyl-tetrahydropyran that is sufficient to inhibit or kill Moraxella osloensis (NBRC 1 1 1460) and Staphylococcus aureus (NBRC 13276) in the liquid medium or on the laundry articles.
- concentration of 3-benzyl- tetrahydropyran in the laundry composition may be in a range from about 160 ppm to about 400 ppm.
- EXAMPLE 1 Deodorant Effect Using Detector Tube
- Samples containing a model malodor system comprising exemplary malodor agents (ammonia 0.005 wt%, trimethylamine 0.003 wt%, and methyl mercaptan 0.001 % from Wako Pure Chemical Industries, Ltd; and diacetyl 1 wt% from V. MANE FILS) diluted in dipropylene glycol (DPG) were prepared and stored in 1 oz. capped, brown glass bottles.
- Another set of samples containing the exemplary malodor agents (ammonia, trimethylamine, methyl mercaptan, and diacetyl), also diluted in DPG, were prepared and treated with BETAHYDRANE (5 times the concentration of the malodor). Each of the samples was stirred at 20°C.
- headspace gas in the vial bottle was passed through a gas detection tube (manufactured by GASTEC Corporation), and plotted against time.
- EXAMPLE 2 Deodorant Effect using Sensory and Gas Chromotography
- Samples containing exemplary malodor agents, isovaleric acid (10 ppm), and nonenal (5 ppm) were prepared and stored in capped, brown glass bottles.
- Samples containing the exemplary malodor agents were treated with BETAHYDRANETM at O.Ox, 0.5x, 1.0x, 2.0x, and 3.0x the concentration of the respective malodor agents.
- BETAHYDRANETM 0.5x, 1.0x, 2.0x, and 3.0x the concentration of the respective malodor agents.
- GC peak area quantitative analysis
- GC analysis was performed using Agilent Technologies 7890B GC, with Agilent Technologies 5977A mass spectrometer, using a DB-WAX(J&W) 60mx0.25mmx0.25pm column; 1 ⁇ injection volume; injection temperature 240°C; 100:1 split ratio; He carrier gas; 1.2ml/min column flow; and Oven 40 (1 min hold) ⁇ 85°C (3°C/min) ⁇ 230°C(10°C/min).
- EXAMPLE 3 Deodorant effect in softener base
- Criteria for sensory evaluation was based on what degree the 32 ppm BETAHYDRANE fabric softener can counteract the model body odor: None (0%); Not so much (0%); Neither (8%); Fee! slightly (43%); Gan feel (48%). Forty-two samples were analyzed for this study.
- testing was performed to determine the MIC values for 3-benzyl- tetrahydropyran against test bacteria Staphylococcus aureus (NBRC 13276) and Moraxella osloensis (NBRC 1 1 1460).
- the testing method included preparation of the test broth solutions, where samples of 3-benzyl-tetrahydropyran were dissolved with ethanol, then diluted with water to provide 4.0 wt% solutions (concentration of ethanol was 6.0%). The 2-fold dilutions of this solution were prepared using Mueller Hinton Broth (MHB).
- Table 2 MIC values for 3-benzyl-tetrahydropyran against Moraxella osloensis.
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- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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Abstract
L'invention concerne des compositions et un procédé pour neutraliser ou masquer les mauvaises odeurs dans des articles de blanchisserie. Le procédé comporte la fourniture d'une composition de blanchisserie comprenant du 3-benzyl-tétrahydropyrane; l'association de la composition de blanchisserie avec un milieu liquide pour mettre en contact les articles de blanchisserie, et la mise en contact des articles de blanchisserie avec le milieu liquide comprenant la composition de blanchisserie. La concentration de 3-benzyl-tétrahydropyrane dans le milieu liquide est d'au moins 15 ppm sur la base de la masse de la composition de blanchisserie. La composition peut être formulée comme une composition détergente ou adoucissante.
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EP4108086A1 (fr) * | 2021-06-24 | 2022-12-28 | BRAIN Biotech AG | Agent microbien ayant une activité inhibitrice de moraxella sp. |
WO2023128948A1 (fr) * | 2021-12-27 | 2023-07-06 | Eczacibasi Tuketim Urunleri Sanayi Ve Ticaret Anonim Sirketi | Produit de nettoyage personnel efficace contre les mauvaises odeurs |
WO2024126316A1 (fr) | 2022-12-12 | 2024-06-20 | Clariant International Ltd | Compositions d'assouplissant pour tissus contenant des cucurbituriles |
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EP4108086A1 (fr) * | 2021-06-24 | 2022-12-28 | BRAIN Biotech AG | Agent microbien ayant une activité inhibitrice de moraxella sp. |
WO2022268990A1 (fr) * | 2021-06-24 | 2022-12-29 | BRAIN Biotech AG | Agent microbien ayant une activité inhibitrice de moraxella sp. |
WO2023128948A1 (fr) * | 2021-12-27 | 2023-07-06 | Eczacibasi Tuketim Urunleri Sanayi Ve Ticaret Anonim Sirketi | Produit de nettoyage personnel efficace contre les mauvaises odeurs |
WO2024126316A1 (fr) | 2022-12-12 | 2024-06-20 | Clariant International Ltd | Compositions d'assouplissant pour tissus contenant des cucurbituriles |
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