GB2205867A - Anhydrides in detergent compositions - Google Patents
Anhydrides in detergent compositions Download PDFInfo
- Publication number
- GB2205867A GB2205867A GB08811819A GB8811819A GB2205867A GB 2205867 A GB2205867 A GB 2205867A GB 08811819 A GB08811819 A GB 08811819A GB 8811819 A GB8811819 A GB 8811819A GB 2205867 A GB2205867 A GB 2205867A
- Authority
- GB
- United Kingdom
- Prior art keywords
- surfactant
- bleach activator
- composition according
- anhydride
- sodium
- 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- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 239000003599 detergent Substances 0.000 title claims abstract description 33
- 150000008064 anhydrides Chemical class 0.000 title claims description 14
- 239000007844 bleaching agent Substances 0.000 claims abstract description 35
- 239000012190 activator Substances 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical class C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 claims abstract description 5
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 claims abstract description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 24
- -1 alkyl sulphates Chemical class 0.000 claims description 21
- 239000002243 precursor Substances 0.000 claims description 20
- 239000004094 surface-active agent Substances 0.000 claims description 16
- 239000002736 nonionic surfactant Substances 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- 239000003945 anionic surfactant Substances 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003093 cationic surfactant Substances 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 5
- 239000002888 zwitterionic surfactant Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 235000019864 coconut oil Nutrition 0.000 claims description 4
- 239000003240 coconut oil Substances 0.000 claims description 4
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 125000001165 hydrophobic group Chemical group 0.000 claims description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
- 229940045872 sodium percarbonate Drugs 0.000 claims description 3
- 239000003760 tallow Substances 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 159000000001 potassium salts Chemical class 0.000 claims description 2
- 229960001922 sodium perborate Drugs 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 150000004685 tetrahydrates Chemical class 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 230000004913 activation Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 description 10
- 229960002163 hydrogen peroxide Drugs 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- BGRWYDHXPHLNKA-UHFFFAOYSA-N Tetraacetylethylenediamine Chemical compound CC(=O)N(C(C)=O)CCN(C(C)=O)C(C)=O BGRWYDHXPHLNKA-UHFFFAOYSA-N 0.000 description 4
- 235000020095 red wine Nutrition 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 2
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 229920001983 poloxamer Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 2
- 235000019832 sodium triphosphate Nutrition 0.000 description 2
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- CIOXZGOUEYHNBF-UHFFFAOYSA-N (carboxymethoxy)succinic acid Chemical compound OC(=O)COC(C(O)=O)CC(O)=O CIOXZGOUEYHNBF-UHFFFAOYSA-N 0.000 description 1
- QBIAZVPERXOGAL-OWOJBTEDSA-N (e)-prop-1-ene-1,3-diamine Chemical compound NC\C=C\N QBIAZVPERXOGAL-OWOJBTEDSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- CFPOJWPDQWJEMO-UHFFFAOYSA-N 2-(1,2-dicarboxyethoxy)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)OC(C(O)=O)CC(O)=O CFPOJWPDQWJEMO-UHFFFAOYSA-N 0.000 description 1
- UURYKQHCLJWXEU-UHFFFAOYSA-N 2-(2-hydroxypropanoyloxy)butanedioic acid Chemical compound CC(O)C(=O)OC(C(O)=O)CC(O)=O UURYKQHCLJWXEU-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- CQWXKASOCUAEOW-UHFFFAOYSA-N 2-[2-(carboxymethoxy)ethoxy]acetic acid Chemical compound OC(=O)COCCOCC(O)=O CQWXKASOCUAEOW-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- WCRKLZYTQVZTMM-UHFFFAOYSA-N 2-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1O WCRKLZYTQVZTMM-UHFFFAOYSA-N 0.000 description 1
- XSVSPKKXQGNHMD-UHFFFAOYSA-N 5-bromo-3-methyl-1,2-thiazole Chemical group CC=1C=C(Br)SN=1 XSVSPKKXQGNHMD-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- LWXKHHXHDYZZFK-UHFFFAOYSA-N cyclopenta-3,4-diene-1,1,2,2,3-pentacarboxylic acid Chemical compound OC(=O)C1=C=CC(C(O)=O)(C(O)=O)C1(C(O)=O)C(O)=O LWXKHHXHDYZZFK-UHFFFAOYSA-N 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 238000004453 electron probe microanalysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XWENCHGJOCJZQO-UHFFFAOYSA-N ethane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C(C(O)=O)C(C(O)=O)C(O)=O XWENCHGJOCJZQO-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- UFZOPKFMKMAWLU-UHFFFAOYSA-N ethoxy(methyl)phosphinic acid Chemical compound CCOP(C)(O)=O UFZOPKFMKMAWLU-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- HKZVDXUEAWCPIQ-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexacarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(C(O)=O)C(C(O)=O)C(C(O)=O)CC(O)=O HKZVDXUEAWCPIQ-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004310 lactic acid Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical class OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- OITDLILIHZRYCA-UHFFFAOYSA-N phenyl 7-methyloctanoate Chemical compound CC(C)CCCCCC(=O)OC1=CC=CC=C1 OITDLILIHZRYCA-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- NJKRDXUWFBJCDI-UHFFFAOYSA-N propane-1,1,2,3-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(C(O)=O)C(O)=O NJKRDXUWFBJCDI-UHFFFAOYSA-N 0.000 description 1
- NJEVMKZODGWUQT-UHFFFAOYSA-N propane-1,1,3,3-tetracarboxylic acid Chemical compound OC(=O)C(C(O)=O)CC(C(O)=O)C(O)=O NJEVMKZODGWUQT-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000344 soap Substances 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 239000004108 vegetable carbon Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 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
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3905—Bleach activators or bleach catalysts
- C11D3/3907—Organic compounds
Abstract
This invention relates to the use of bleach activators in detergent compositions. These activators comprise one or more substituted derivatives of 5-norbornene-2,3-dicarboxylic anhydride ("nadic anhydride") or an analogue thereof. The use of these compounds enables the bleach activation to take place at relatively lower temperatures than used hitherto.
Description
ANHYDRIDES IN DETERGENT COMPOSITIONS
The present invention relates to the use of anhydrides as bleach activators, especially in detergent compositions.
Compounds such as tetraacetyl ethylene diamine (hereafter referred to as "TAED") are well known. Processes for the production of such compounds are disclosed for instance in published German patent application no. 2832021. These compounds are said to be efficient in activating the conventional inorganic salts used as bleach precursors in detergent compositions and generate peracetic acid in situ by the reaction thereof with alkaline hydrogen peroxide. The activating agent for the bleach precursor is the so-called bleach activator. Specific examples of such bleach precursors are sodium perborate and sodium percarbonate. In the absence of the activators the bleach precursor is satisfactorily effective only at the boil, its effectiveness being very slow at lower temperatures.The use of compounds such as TAED enable the bleach precursor to function more effectively at temperatures of the order of 60 C.
It has now been found that certain anhydrides function at least as efficiently as conventional additives in activating the bleach precursor in detergent compositions, especially at low temperatures.
Accordingly the present invention is a detergent composition comprising (i) a surfactant selected from anionic, nonionic, zwitterionic and cationic surfactants and mixtures thereof, (ii) a precursor compound capable of giving rise to hydrogen peroxide in the presence of a bleach activator, (iii) a bleach activator (iv) a suds suppressing agent and (v) a detergent builder, characterised in that the bleach activator comprises one or more substituted derivatives of 5-norbornene-2,3-dicarboxylic anhydride (hereafter referred to as nnadic anhydride" for convenience) of the general formula (I):
wherein:: zl and z2 are the same or different groups selected from H,
halogen, nitrile, hydroxyl and 0
-O-C-R
in which R is a simple or substituted C1-C10 alkyl and Y is a
-CH2-, -CH=CH-, -O-, -S- or an NR1 group and wherein R1 is H or
R group as defined above.
Specific examples of the compounds falling within the generic formula (I) above include: 5,6-dibromonadic anhydride; 5,6-di-oacetyl-nadic anhydride; 5,6-dihydronadic anhydride; and 4,5-dibromo3,6-endoxo-1,2,3,6-tetrahydrophthalic anhydride.
Methods of preparing substituted nadic anhydrides are well known in the art. For instance, 5,6-dibromonadic anhydride can be prepared according to the process described in GB-A-1079015 and in
J. Am. Chem. Soc., Vol 81, pp 1655 (1959).
The bleach activators of the present invention are powerful.
They can therefore be used as such or in conjunction with other conventional activators such as TAED, phthalic anhydride, maleic anhydride, succinic anhydride isononanoyl oxybenzene sulphonate (also known as isonobs') and tetracetyl glycoluril (also known as "TAGU") and the like or with mixtures of such known activators.
Any of the well known surfactants can be used in the detergent compositions of the present invention. A typical list of these surfactants can be found in EP 0120591 and in USP 3,663,961.
Examples of water soluble anionic surfactants include the salts of alkyl benzene sulphonates, paraffin sulphonates, alpha-olefin sulphonates, alkyl glyceryl ether sulphonates and 2-acyloxy alkane-l-sulphonate, and beta-alkyloxy alkane sulphonate.
Similarly, salts of alkyl sulphates, alkyl polyalkoxy ether sulphates, alpha-sulpho-carboxylates and their esters, fatty acid monoglyceride sulphates and sulphonates and alkyl phenol polyalkoxy ether sulphates may also be used.
Suitable examples of the above surfactants are linear straight chain alkyl benzene sulphonates and methyl-branched alkyl sulphates having in either case 8-16 carbon atoms in the alkyl group.
Other anionic detergent compounds suitable for use herein include the sodium alkyl glyceryl ether sulphonates derived from tallow and coconut oil; sodium fatty acid monoglyceride sulphonates and sulphates derived from coconut oil; and sodium or potassium salts of Cg-C12 alkyl phenol alkylene oxide ether sulphate containing up to 10 alkylene oxide units per molecule. Mixtures of anionic surfactants may also be used.
A substantial list of such compounds can be found in e.g.
McCutcheon's Dictionary of Emulsifiers and Detergents, International Sedition (1981), published by the Manufacturing Confectioner
Publishing Co. and in "Surfactants Europa: A Directory of Surface
Active Agents available in Europe", Ed. Gordon L. Hollis, Vol 1 (1982), published by George Goodwin.
The nonionic surfactants which may be used in the present invention are condensates of an alkylene oxide e.g. ethylene oxide with a hydrophobic group to form a surfactant having an appropriate hydrophilic-lipophilic balance (HLB) in the range from 8 to 17, suitably from 9.5 to 13.5, preferably from 10 to 12.5. The hydrophobic group may be an aliphatic or aromatic type and the length of the polyoxyethylene group condensed therewith can be readily adjusted to yield a water-soluble compound having the desired degree of HLB.
Examples of suitable nonionic surfactants include: (a) The polyethylene oxide condensates of alkyl phenol in which the
alkyl group e.g. contains from 6 to 12 carbon atoms and in
which from 3 to 30 moles, preferably 5 to 14 moles of ethylene
oxide are present. Other examples include a mole of
dodecylphenol condensed with 9 moles of ethylene oxide, a mole
of dinonylphenol condensed with 11 moles of ethylene oxide and
a mole of nonylphenol and octadecylphenol condensed with
13 moles of ethylene oxide.
(b) The nonionic surfactant may also be formed as a condensation
product of a mole of primary or secondary Cg-C24 aliphatic
alcohols with from 2 to 40 moles, preferably 2 to 9 moles of
ethylene oxide.
Specific examples of nonionic surfactants useful for the purposes of the invention include the various grades of Dobanol (Registered Trade Mark, supplied by Shell) Lutensol (Registered
Trade Mark, supplied by BASF) and Synperonics (Registered Trade
Mark, supplied by ICI).
Other useful nonionic surfactants include the synthetic nonionic detergents available on the market under "Pluronics"(Registered Trade Mark) and supplied by Wyandotte
Chemicals Corporation.
Zwitterionic compounds such as betaines and sulphobetaines, particularly those with a Cg-C16 alkyl substituent on the nitrogen atom can also be used as surfactants.
Examples of cationic surfactants that can be used include e.g.
quaternary ammonium compounds and compounds of a semi-polar nature, for example amine oxides. Suitable quaternary ammonium compounds are the mono Cg-C16, N-alkyl or alkenyl ammonium compounds in which remaining N valences are methyl, hydroxyethyl or hydroxypropyl groups. Suitable examples of amine oxides are the mono Cg-C20,
N-alkyl or alkenyl amine oxides and the propylene-1,3-diamine dioxides in which the remaining N valences are methyl, hydroxyethyl or hydroxypropyl substituents.
The detergent compositions can comprise from 1 to 70% w/w, suitably from 1 to 20X w/w of surfactant. Mixtures of anionic with nonionic or zwitterionic surfactant types are preferred.
Suitable precursor compounds which are capable of giving rise to hydrogen peroxide in the presence of a bleach activator include sodium perborate mono and tetrahydrate, sodium percarbonate, sodium persilicate and the clathrate 4Na2S04:2H202:lNaCl.
If clathrate materials are used a separate source of alkalinity will be required and for stability reasons these are preferably stored separately from the hydrogen peroxide source. The precursor compound (ii) capable of giving rise to hydrogen perox-ide can be present in an amount of from 1 to 40X w/w suitably from 5 to 35% by weight, preferably from 10 to 30Z by weight of the total composition.
In the detergent compositions of the present invention the molar ratio of hydrogen peroxide generated from a bleach precursor to bleach activator is suitably greater than 1.5:1, preferably at least 2.0. Under the usage conditions encountered in domestic laundry practice, the molar ratio of bleach precursor to bleach activator is generally greater than 5.0:1 and is most preferably greater than 10:1.
Suds suppressing agents which are useful in the detergent compositions of the invention are suitably selected from silicone, wax, vegetable and hydrocarbon oil and phosphate ester varieties.
Suitable silicone suds controlling agents include polydimethylsiloxanes having a molecular weight in the range from 200 to 200,000 and a kinematic viscosity in the range from 20 to 2,000,000 mm2/s (cSt), preferably from 3000 to 30,000 mm2/s (cSt), and mixtures of siloxanes and hydrophobic silanated (e.g.
trimethylsilanated) silica having a particle size in the range from 10 to 20 millimicrons and a specific surface area above 50 m2/g.
Suitable waxes include microcrystalline waxes having a melting point in the range from 65"C to 1000C, a molecular weight in the range from 4,000-10,000 and a penetration value of at least 6, measured at 77"C by ASTM-D1321 and also paraffin waxes, synthetic waxes and natural waxes. Suitable phosphate esters include mono- and/or di-C16-C22 alkyl or alkenyl phosphate esters, and the corresponding mono- and/or di alkyl or alkenyl ether phosphates containing up to 6 ethoxy groups per molecule.
Suds suppressors are normally present in an amount from 0.01 to 5% w/w of the total composition depending upon the type of suds suppressor used, and is preferably from 0.1 to 2% w/w.
A highly preferred component of detergent compositions in accordance with the invention is one or more detergent builder salts which may comprise up to 90Z of the composition, more typically from 10 to 70Z by weight thereof. Suitable detergent builder salts useful herein can be of the polyvalent inorganic and polyvalent organic types or mixtures thereof. Examples of suitable water-soluble, inorganic alkaline detergent builder salts include the alkali metal carbonates, borates, phosphates, pyrophosphates, tripolyphosphates and bicarbonates.
Examples of suitable organic alkaline detergency builder salts are water-soluble polycarboxylates such as the salts of nitrilotriacetic acid, lactic acid, glycollic acid and ether derivatives thereof; succinic acid, malonic acid, (ethylenedioxy)diacetic acid, maleic acid, diglycollic acid, tartaric acid, tartronic acid and fumaric acid; citric acid, aconitic acid, citraconic acid, carboxymethyloxysuccinic acid, lactoxysuccinic acid, and 2-oxy-1,1,3propane tricarboxylic acid; oxydisuccinic acid, 1,1,2,2-ethane tetracarboxylic acid, 1,1,3,3-propane tetracarboxylic acid and 1,1,2,3-propane tetracarboxylic acid; cyclopentane cis, cis,cistetracarboxylic acid, cyclopentadiene pentacarboxylic acid, 2,3,4,5-tetrahydrofuran-cis, cis, cis-tetracarboxylic acid, 2,5-tetrahydrofuran-cis-dicarboxylic acid, 1,2,3,4,5,6-hexanehexacarboxylic acid, mellitic acid, pyromellitic acid and the phthalic acid derivatives.
Water-insoluble detergent builders can also be used. A specific example of such builders are the zeolites especially-the sodium type A zeolite typified by SASIL (Registered Trade Mark).
Mixtures of organic and/or inorganic builders can also be used.
Chelating agents, soil suspending and anti-redeposition agents, optical brightening agents, enzymes, colours and perfumes may also be added to the detergent composition.
Chelating agents that can be incorporated include citric acid, nitrilotriacetic and ethylene diamine tetra acetic acids and their salts, organic phosphonate derivatives such as those disclosed in US
Patent Nos. 3,213,030, 3,433,021, 3,292,121 and 2,599,807 and carboxylic acid builder salts such as those disclosed in US Patent
No. 3,308,067. The chelating agents can be present in amounts ranging from 0.1 to 3X, suitably from 0.2 to 2Z by weight of the total composition.
According to a further embodiment the present invention is a detergent composition comprising (i) a surfactant selected from anionic, nonionic, zwitterionic and cationic surfactants and mixtures thereof, (ii) a precursor compound capable of giving rise to hydrogen peroxide in the presence of a bleach activator, (iii) a bleach activator, (iv) a suds suppressing agent and (v) a detergent builder, wherein the bleach activator comprises one or more substituted derivatives of 5-norbornene-2,3-dicarboxylic anhydride of the general formula (I) above.
The detergent compositions containing the bleach activators of the present invention may contain, in addition, minor conventional additives such as fragrances perfumes and the like.
Thus the bleach activators of the present invention should find wide use in detergent compositions which use the inorganic bleach precursors. The fact that these anhydrides activate the bleach precursors at relatively lower temperatures than those used hitherto should enable a considerable energy saving to be achieved, when the detergents are used.
The present invention is further illustrated with reference to the accompanying Examples.
Example
Washing/bleaching tests were carried out on standard stained cloth swatches (EMPA red wine and Krefeld Tea, 2" x 6") using the base detergent powder composition (Table 1) and the various bleach activators described in Table 2 in a terg-o-tometer. The terg-o-tometer was maintained at a constant temperature of 40"C and operated at 75 rpm.
4g of base detergent plus 0.75g sodium perborate tetrahydrate plus activator as described in Table 2 was added to one litre of tap water at 40"C, having a hardness of about 290 ppm as calcium carbonate. One red wine swatch and one tea swatch was added, then the composition agitated for 30 minutes at 400C after which the swatches were removed, rinsed in tap water and dried at 24"C. The reflectance of the swatches were taken before and after using an ICS
Micromatch reflectometer and the percentage stain removal (Z SR) calculated by applying the following formula: x SR - L sample - L redwine x 100
L white - L redwine
Three replicates were run and the average result is quoted (Table 2).
Table 1
X
Linear sodium alkyl benzene sulphonate 8.0 (mean length of alkyl chain C11.5) Ethoxylated tallow alcohol (14 EO) 2.9
Sodium soap (chain length C12 - C16: 13-26% 3.5
C18 - C22: 74-87%)
Sodium triphosphate 43.8
Sodium silicate (SiO2:Na2O = 3.3: :1) 7.5
Magnesium silicate 1.9
Carboxymethylcellulose 1.2
Sodium ethylenediaminetetraacetate 0.2
Sodium sulphate ~~~ 21.2
Water 9.8
100.0
Table 2
Percentage Stain Removal of Activators at 5-1Z Levels C.25g 0.20g 0.15g 0.10g 0.05g
Activator (5Z) (4Z) (3Z) (2Z) (1%) 5,6-Dibromonadic 87.0 84.8 83.1 82.0 80.3 anhydride 5,6-Di-O-acetyl 83.4 82.4 81.4 80.5 79.5 nadic anhydride 5,6-Dihydro nadic 82.6 81.7 81.0 79.9 79.5 anhydr ide 4,5-Dibromo-3,6-endoxo-1,2, 85.1 83.2 82.0 81.3 80.0 3,6-tetrahydrophthalic anhydride
With no activator present, sodium perborate tetrahydrate gives a percentage stain removal of 76.0%.
Claims (10)
1. A detergent composition comprising (i) a surfactant selected from anionic, nonionic, zwitterionic and cat ionic surfactants and mixtures thereof, (ii) a precursor compound capable of giving rise to hydrogen peroxide in the presence of a bleach activator, (iii) a bleach activator (iv) a suds suppressing agent and (v) a detergent builder, characterised in that the bleach activator comprises one or more substituted derivatives of 5-norbornene-2,3-dicarboxylic anhydride (hereafter referred to as "nadic anhydride" for convenience) of the general formula (I):
wherein:: zl and z2 are the same or different groups selected from H,
halogen, nitrile, hydroxyl and 0
-O-C-R
in which R is a simple or substituted C1-C10 alkyl and Y is a
-CH2-, -CH=CH-, -O-, -S- or an NR1 group and wherein R1 is H or
R group as defined above.
2. A detergent composition according to claim l wherein the compound of the general formula (I) above is selected from 5,6-dibromonadic anhydride; 5,6-di-o-acetyl-nadic anhydride; 5,6-dihydronadic anhydride; and 4,5-dibromo3,6-endoxo-1,2,3,6- tetrahydrophthalic anhydride.
3. A composition according to claim 1 or 2 wherein the surfactant is an anionic surfactant selected from linear straight chain alkyl benzene sulphonates and methyl-branded alkyl sulphates having in either case 8-16 carbon atoms in the alkyl group; sodium alkyl glyceryl ether sulphonates derived from tallow or coconut oils sodium fatty acid monoglyceride sulphonates and sulphates derived from coconut oil; and sodium and potassium salts of Cg-C12 alkyl phenol alkylene oxide ether sulphate containing up to 10 alkylene oxide units.
4. A composition according to claim 1 or 2 wherein the surfactant is a non-ionic surfactant being a condensate of either an alkylene oxide with a hydrophobic group which has a hydrophilic-lipophilic balance (HLB) in the range from 8 to 17, or of a mole of primary or secondary C8-C24 aliphatic alcohol with 2-9 moles of ethylene oxide.
5. A composition according to claims 1 or 2 wherein the surfactant is a cationic surfactant which is either a quaternary ammonium compound or an amine oxide.
6. A composition according to any one of the preceding claims wherein the composition comprises 1 to 70Z w/w of surfactant.
7. A composition according to any one of the preceding claims wherein the precursor compounds which are capable of giving rise to hydrogen peroxide in the presence of a bleach activator comprise sodium perborate mono- or tetrahydrate, sodium percarbonate, sodium persilicate or the clathrate 4Na2S04.2H202:lNaCl.
8. A composition according to any one of the preceding claims wherein the precursor compound capable of giving rise to hydrogen peroxide is present in an amount from 1 to 40X w/w of the total composition.
9. A composition according to any one of the preceding claims wherein the amount of precursor compound used is such that the mole ratio of hydrogen peroxide generated from the precursor to bleach activator is greater than 1.5:1.
10. A detergent composition comprising (i) a surfactant selected from anionic, nonionic, zwitterionic and cationic surfactants and mixtures thereof, (ii) a precursor compound capable of giving rise to hydrogen peroxide in the presence of a bleach activator, (iii) a bleach activator, (iv) a suds suppressing agent and (v) a detergent builder, wherein the bleach activator comprises one or more substituted derivatives of 5-norbornene-2,3-dicarboxylic anhydride of the general formula (I) in claim 1 above.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878711927A GB8711927D0 (en) | 1987-05-20 | 1987-05-20 | Anhydrides in detergent compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8811819D0 GB8811819D0 (en) | 1988-06-22 |
| GB2205867A true GB2205867A (en) | 1988-12-21 |
Family
ID=10617639
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB878711927A Pending GB8711927D0 (en) | 1987-05-20 | 1987-05-20 | Anhydrides in detergent compositions |
| GB08811819A Withdrawn GB2205867A (en) | 1987-05-20 | 1988-05-19 | Anhydrides in detergent compositions |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB878711927A Pending GB8711927D0 (en) | 1987-05-20 | 1987-05-20 | Anhydrides in detergent compositions |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB8711927D0 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4966723A (en) * | 1988-02-11 | 1990-10-30 | Bp Chemicals Limited | Bleach activators in detergent compositions |
-
1987
- 1987-05-20 GB GB878711927A patent/GB8711927D0/en active Pending
-
1988
- 1988-05-19 GB GB08811819A patent/GB2205867A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4966723A (en) * | 1988-02-11 | 1990-10-30 | Bp Chemicals Limited | Bleach activators in detergent compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8811819D0 (en) | 1988-06-22 |
| GB8711927D0 (en) | 1987-06-24 |
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