WO2022122266A1 - Use of lactam - Google Patents
Use of lactam Download PDFInfo
- Publication number
- WO2022122266A1 WO2022122266A1 PCT/EP2021/080768 EP2021080768W WO2022122266A1 WO 2022122266 A1 WO2022122266 A1 WO 2022122266A1 EP 2021080768 W EP2021080768 W EP 2021080768W WO 2022122266 A1 WO2022122266 A1 WO 2022122266A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- lactam
- hydrogen
- toilet
- reduction
- malodour
- Prior art date
Links
- 150000003951 lactams Chemical class 0.000 title claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 239000001257 hydrogen Substances 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 30
- 210000002700 urine Anatomy 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000005188 oxoalkyl group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- -1 mono-substituted phenyl group Chemical group 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- 241000079899 Pedipes mirabilis Species 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 11
- 241000588770 Proteus mirabilis Species 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- HHCPGPHTKXVNHA-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-methylidenepyrrol-2-one Chemical compound C1=CC(Cl)=CC=C1C1=CC(=O)NC1=C HHCPGPHTKXVNHA-UHFFFAOYSA-N 0.000 description 4
- YSZWLEFVAJQHJS-UHFFFAOYSA-N 5-methylidene-4-(4-methylphenyl)pyrrol-2-one Chemical compound C1=CC(C)=CC=C1C1=CC(=O)NC1=C YSZWLEFVAJQHJS-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000001218 confocal laser scanning microscopy Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- PZQOWENOZPCUSJ-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-hydroxy-5-methyl-1H-pyrrol-2-one Chemical compound CC1(O)NC(=O)C=C1C1=CC=C(Cl)C=C1 PZQOWENOZPCUSJ-UHFFFAOYSA-N 0.000 description 2
- OVLMWAKWSBFBBQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-hydroxy-5-methylfuran-2-one Chemical compound CC1(O)OC(=O)C=C1C1=CC=C(Cl)C=C1 OVLMWAKWSBFBBQ-UHFFFAOYSA-N 0.000 description 2
- CPAOXJPVYYJEAF-UHFFFAOYSA-N 5-hydroxy-5-methyl-4-(4-methylphenyl)-1H-pyrrol-2-one Chemical compound CC1=CC=C(C=C1)C1=CC(=O)NC1(C)O CPAOXJPVYYJEAF-UHFFFAOYSA-N 0.000 description 2
- JTBGHWGTJYXHMI-UHFFFAOYSA-N 5-hydroxy-5-methyl-4-(4-methylphenyl)furan-2-one Chemical compound CC1=CC=C(C=C1)C1=CC(=O)OC1(C)O JTBGHWGTJYXHMI-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000219470 Mirabilis Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 108010046334 Urease Proteins 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000012491 analyte Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012800 visualization Methods 0.000 description 2
- WEJRYKSUUFKMBC-UHFFFAOYSA-N 1-(4-chlorophenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C(Cl)C=C1 WEJRYKSUUFKMBC-UHFFFAOYSA-N 0.000 description 1
- NOXKUHSBIXPZBJ-UHFFFAOYSA-N 1-(4-methylphenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C(C)C=C1 NOXKUHSBIXPZBJ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 241000588917 Citrobacter koseri Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000495778 Escherichia faecalis Species 0.000 description 1
- 229910005390 FeSO4-7H2O Inorganic materials 0.000 description 1
- 229910005444 FeSO4—7H2O Inorganic materials 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- 241000588772 Morganella morganii Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 244000110797 Polygonum persicaria Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241001240958 Pseudomonas aeruginosa PAO1 Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000193985 Streptococcus agalactiae Species 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- CKMXBZGNNVIXHC-UHFFFAOYSA-L ammonium magnesium phosphate hexahydrate Chemical compound [NH4+].O.O.O.O.O.O.[Mg+2].[O-]P([O-])([O-])=O CKMXBZGNNVIXHC-UHFFFAOYSA-L 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- VIHAEDVKXSOUAT-UHFFFAOYSA-N but-2-en-4-olide Chemical compound O=C1OCC=C1 VIHAEDVKXSOUAT-UHFFFAOYSA-N 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229940060799 clarus Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229940109239 creatinine Drugs 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000010800 human waste Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 108010054624 red fluorescent protein Proteins 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000002470 solid-phase micro-extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910052567 struvite Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000012138 yeast extract 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
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/28—Heterocyclic compounds containing nitrogen in the ring
Definitions
- the invention relates to an improvement in the field of toilet hygiene, in particular to the use of a lactam to improve toilet hygiene.
- the invention relates in a first aspect to the use of a lactam composition to improve toilet hygiene, the use comprising treatment of a toilet surface, wherein the composition comprises from 0.0001 to 5 wt.% of a lactam; wherein the use involves reduction of malodour; or wherein the use involves reduction of unwanted urine scale formation in the toilet; wherein the lactam is of formula (I) or (II): wherein:
- Ri and R2 are each independently selected from hydrogen, halogen, alkyl, cycloalkyl, alkoxy, oxoalkyl, alkenyl, heterocyclyl, heteroaryl, aryl and aralalkyl; and
- R4 and R 5 are independently selected from hydrogen, aryl, heterocyclyl, heteroaryl, and arylalkyl;
- Re is selected from hydrogen and methyl
- the lactam is present at a level of from 0.0001 to 2.5 wt.%, preferably from 0.0001 to 1 wt.%, more preferably from 0.001 to 1 wt.%.
- the use involves reduction of malodour.
- the reduction of malodour involves the reduction of malodour associated with urine, in particular relating to the reduction of malodour associated with phenol and indole; or the use involves reduction of unwanted urine scale formation in the toilet.
- the reduction of unwanted urine scale formation in the toilet involves the inhibition of P. mirabilis.
- the lactam is of formula (I) or (II): wherein:
- the lactam of formula (I) or (II), R1, R 4 and R 5 are H;
- R 3 is H, or (CH 2 ) n N + (CH 3 ) 3 , where n is an integer from 1 to 16, preferably 2 to 8;
- R 2 is a phenyl group, or a monosubstituted phenyl group; preferably R 2 is selected from phenyl, 4-fluorophenyl, 2- fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 4-bromophenyl and 4-methylphenyL
- the lactam is a lactam selected from:
- lactam is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N
- Figure 2 relates to example 2 and shows the effect of malodour control (indole) by lactam
- Figure 4 relates to example 3 and depicts a graph showing the effect of reduction of P. Mirabilis by lactam
- indefinite article “a” or “an” and its corresponding definite article “the” as used herein means at least one, or one or more, unless specified otherwise.
- the use involves reduction of malodour, and/or the use involves reduction of unwanted urine scale formation in the toilet.
- the urine scale that form is at least in part due to the formation of crystals.
- Proteus mirabilis produces ureases that hydrolyse urea releasing carbon dioxide and ammonia, increasing the pH of urine, and leading to struvite and apatite crystalline deposits.
- Proteus mirabilis inhibition is concomitant with crystal formation inhibition.
- Re is selected from hydrogen and methyl
- R1 is hydrogen.
- R 3 is hydrogen, or (CH 2 ) n N + (R a ) 3 , where n is an integer from 1 to 16, preferably 2 to 8, and where each R a is independently H or C1-4 alkyl, more preferably R a is CH 3 ;
- R4 is hydrogen.
- R 5 is hydrogen.
- Re is hydrogen.
- R 7 is hydrogen.
- R 2 is aryl or aralalkyl. More preferably, R 2 is a phenyl group or a substituted phenyl group, for example, a monosubstituted phenyl group. Substitution may be ortho, meta, or para.
- R 2 may be selected from phenyl, 4-fluorophenyl, 2-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 4-bromophenyl and 4-methylphenyl.
- R1, R 4 and R 5 are H;
- R 3 is H, or (CH 2 ) n N + (CH 3 ) 3 , where n is an integer from 1 to 16, preferably 2 to 8; and
- R 2 is a phenyl group, or a mono-substituted phenyl group; preferably R 2 is selected from phenyl, 4- fluorophenyl, 2-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 4-bromophenyl and 4- methylphenyl.
- the lactam is of formula (I), Ri, FU and R 5 are H; R 3 is H, or (CH 2 ) n N + (CH 3 ) 3 , where n is an integer from 1 to 16, preferably 2 to 8; and R 2 is a phenyl group, or a mono-substituted phenyl group; preferably R 2 is selected from phenyl, 4- fluorophenyl, 2-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 4-bromophenyl and 4- methylphenyl.
- the lactam is cationic in nature, it can be used as such, or suitably with a counterion (e.g. iodide)
- a counterion e.g. iodide
- the lactam is a lactam selected from:
- the lactam is delivered from an aqueous based composition, or an organic solvent based composition, most preferably an aqueous based composition.
- the composition comprises from 0.0002 to 0.1 wt.%, preferably from 0.001 to 0.1 wt.% of a lactam.
- the toilet surface to be treated is selected from ceramics (e.g. porcelain).
- composition may comprise further ingredients such as surfactants, chelating agents, thickeners, pH modifiers.
- aqueous layer was extracted with dichloromethane (100 mL), and the combined organic layers washed with a 1 :1 mixture of water and saturated aqueous sodium hydrogen carbonate solution (100 mL), dried (MgSCU) and filtered. Silica was added to the filtrate and the mixture stirred for 10 minutes before filtering through a plug of silica, washing through with dichloromethane followed by a 3:1 mixture of dichloromethane:diethyl ether. Fractions containing the desired product were combined and concentrated under reduced pressure.
- the lactam used was denoted as ‘488’ and is 4-(4-chlorophenyl)-5-methylene-pyrrol-2-one.
- the artificial urine medium composition was shown in table 1 .
- a consortium of bacterial cultures was prepared by mixing equal volumes of 10 8 cells/ ml of
- a 1 : 40 dilution mix of bacterial culture mix and sterile artificial urine medium was prepared in bulk and 5 ml of this mix was transferred to sterile GC vials.
- 1 % stock of Lactam 488 was prepared in DMSO. Different concentrations of lactam 488 corresponding to 50, 200 and 400 ppm was added to the above prepared GC vials in duplicates.
- a positive control was set up simultaneously without addition of Lactam 488.
- the vials were incubated at 37°C for 48 hours. After 48 hours, the vials were subjected to GC analysis. Sample vials were placed in CombiPAL vial holder. Auto SPME accessory was used to perform the analysis.
- GC-MS (SIM) conditions Instrument: Perkin Elmer Clarus 500 Gas chromato graph -Mass spectrometer.
- GC Conditions were: GC column: CP WAX (30m x 0.25 mm ID x 0.25 pm thickness); carrier gas: Helium (1 mL/min); oven program: Initial temperature 35°C hold for 5 min; ramp: 10°C per minute to 230°C hold for 5 min; run time: 29.5 min; Injection port temperature: 230°C.
- MS Conditions were: Inlet line Temperature: 200°C; Electron Energy: 70eV; Source Temperature: 180°C; Multiplier voltage: 400 V
- the sample vial was equilibrated at 60 degrees for 5 minutes. Sampling time was 2 minutes. Desorption time is 2 minutes. Post fiber conditioning time is 38 minutes. Total run time is 40 minutes.
- Operation of a GC/MS in SIM mode allows for detection of specific analytes with increased sensitivity.
- the MS gathers data for masses of interest rather than looking for all masses over a wide range.
- the instrument is set to look for only masses of interest it can be specific for a particular analyte of interest. Hence, they were analysed using SIM mode.
- two more than two ions are monitored per compound and the ratios of those ions will be unique to the analyte of interest.
- the ions monitored for each molecule is captured in Table 2.
- the mass scan rate and dwell times (the time spent looking at each mass) are adjusted. Using this method, we could detect Phenol (Retention time-18.5) and Indole (Retention time- 22.4).
- the odour generated from the sample without Lactam was considered as 100%.
- the amount of odour generated is noted down from the peak area of the MO peaks. In comparison to this peak, the odour generated in presence of Lactam was calculated.
- the peak areas of Phenol and Indole from the sample only with bugs were noted down and considered to be 100%.
- the peak areas of these two peaks in the sample with Lactam was noted down and % reduction with respect to the sample without lactam was compared and plotted in a graph shown in figures 1 and 2 with the data also shown in tables 3 and 4.
- a multi-strain biofilm experiment was carried out with ds-red labelled P. mirabilis Hauser 1885, m-turquoise labelled P. aeruginosa PAO1 -uw and eGFP labelled S. aureus SH1000.
- the OD600 for each strain was adjusted for the inoculum at 0.05 with artificial urine medium in polystyrene 24-well plates (Greiner), left seeding for 2 h statically at 37 °C and incubated for a further 22 h at 70 rpm for a total of 72 h.
- Pr. mirabilis was grown first, followed by P. aeruginosa and finally S. aureus for a total of 72 h.
- CLSM Confocal Laser Scanning Microscopy
- the acquisition settings depended on the fluorescence: pinhole 1 .0, laser intensity 5%-15% and gain between 450 and 700 for bio-fluorescent strains. Nevertheless, once adjusted to optimize the visualization, settings were never modified within an experiment to facilitate an unbiased comparison.
- the Z-stack height was set for each acquisition in a new well by starting from the first point where no emission was detected (just prior to the start of the biofilm), through the biofilm itself, until a point of no emission was again reached, which was set as the last slice. Spacing, once set, was kept constant within the experiment.
- Biofilms were analysed and quantified using a TECANTM infinite F200 PRO plate reader.
- 3D pictures were processed using the Maximum intensity Projection function in Zen 2.3 SP1 (black) software (Carl Zeiss, Jena, Germany). This tool generates a bi-dimensional (2D) image per channel, constituted by pixels containing the maximum value over all images in the Z-stack at the single pixel location.
- Each new picture was exported in tiff format (64bit) with no compression into Zen 2.3 (Blue edition).
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CN202180082476.2A CN116583586A (en) | 2020-12-09 | 2021-11-05 | Use of lactams |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1988000184A1 (en) * | 1986-06-27 | 1988-01-14 | Gaf Corporation | Surface active lactams |
AU2015200142A1 (en) * | 2006-01-24 | 2015-02-05 | Unilever Plc | Novel lactams |
US9586901B2 (en) * | 2006-01-24 | 2017-03-07 | Unilever Plc | Lactams |
WO2020053108A1 (en) * | 2018-09-14 | 2020-03-19 | Unilever Plc | Mousse composition |
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2021
- 2021-11-05 EP EP21814687.6A patent/EP4259765A1/en active Pending
- 2021-11-05 WO PCT/EP2021/080768 patent/WO2022122266A1/en active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1988000184A1 (en) * | 1986-06-27 | 1988-01-14 | Gaf Corporation | Surface active lactams |
AU2015200142A1 (en) * | 2006-01-24 | 2015-02-05 | Unilever Plc | Novel lactams |
US9586901B2 (en) * | 2006-01-24 | 2017-03-07 | Unilever Plc | Lactams |
WO2020053108A1 (en) * | 2018-09-14 | 2020-03-19 | Unilever Plc | Mousse composition |
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