EP2855654A1 - Stabilization of phthalimido percarboxylic acids with disaccharides - Google Patents
Stabilization of phthalimido percarboxylic acids with disaccharidesInfo
- Publication number
- EP2855654A1 EP2855654A1 EP12726408.3A EP12726408A EP2855654A1 EP 2855654 A1 EP2855654 A1 EP 2855654A1 EP 12726408 A EP12726408 A EP 12726408A EP 2855654 A1 EP2855654 A1 EP 2855654A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- phthalimido
- mixture
- acid
- disaccharide
- weight
- 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- Withdrawn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
- 150000002016 disaccharides Chemical class 0.000 title claims abstract description 29
- 239000002253 acid Substances 0.000 title claims description 21
- 150000007513 acids Chemical class 0.000 title claims description 19
- 125000005544 phthalimido group Chemical group 0.000 title claims description 18
- 230000006641 stabilisation Effects 0.000 title description 4
- 238000011105 stabilization Methods 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 68
- -1 phthalimido percarboxylic acid Chemical compound 0.000 claims abstract description 42
- 239000003599 detergent Substances 0.000 claims abstract description 24
- 239000007844 bleaching agent Substances 0.000 claims abstract description 12
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 11
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 11
- 239000004327 boric acid Substances 0.000 claims description 11
- 239000008101 lactose Substances 0.000 claims description 11
- FSBGUSGSQKUNCC-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)hexaneperoxoic acid Chemical compound C1=CC=C2C(=O)N(C(CCCC)C(=O)OO)C(=O)C2=C1 FSBGUSGSQKUNCC-UHFFFAOYSA-N 0.000 claims description 8
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 6
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 claims description 3
- AYRXSINWFIIFAE-SCLMCMATSA-N Isomaltose Natural products OC[C@H]1O[C@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)[C@@H](O)[C@@H](O)[C@@H]1O AYRXSINWFIIFAE-SCLMCMATSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims description 3
- NBGXQZRRLOGAJF-UHFFFAOYSA-N Maltulose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)(CO)OCC1O NBGXQZRRLOGAJF-UHFFFAOYSA-N 0.000 claims description 3
- VSRVRBXGIRFARR-CIYSLCTESA-N Neohesperidose Natural products O([C@@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1 VSRVRBXGIRFARR-CIYSLCTESA-N 0.000 claims description 3
- AYRXSINWFIIFAE-UHFFFAOYSA-N O6-alpha-D-Galactopyranosyl-D-galactose Natural products OCC1OC(OCC(O)C(O)C(O)C(O)C=O)C(O)C(O)C1O AYRXSINWFIIFAE-UHFFFAOYSA-N 0.000 claims description 3
- OVVGHDNPYGTYIT-VHBGUFLRSA-N Robinobiose Natural products O(C[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](C)O1 OVVGHDNPYGTYIT-VHBGUFLRSA-N 0.000 claims description 3
- HIWPGCMGAMJNRG-ACCAVRKYSA-N Sophorose Natural products O([C@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HIWPGCMGAMJNRG-ACCAVRKYSA-N 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims description 3
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 3
- HDTRYLNUVZCQOY-BTLHAWITSA-N alpha,beta-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-BTLHAWITSA-N 0.000 claims description 3
- VSRVRBXGIRFARR-OUEGHFHCSA-N alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranose Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O VSRVRBXGIRFARR-OUEGHFHCSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims description 3
- DLRVVLDZNNYCBX-ZZFZYMBESA-N beta-melibiose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 DLRVVLDZNNYCBX-ZZFZYMBESA-N 0.000 claims description 3
- HIWPGCMGAMJNRG-UHFFFAOYSA-N beta-sophorose Natural products OC1C(O)C(CO)OC(O)C1OC1C(O)C(O)C(O)C(CO)O1 HIWPGCMGAMJNRG-UHFFFAOYSA-N 0.000 claims description 3
- 235000013681 dietary sucrose Nutrition 0.000 claims description 3
- DLRVVLDZNNYCBX-CQUJWQHSSA-N gentiobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)C(O)O1 DLRVVLDZNNYCBX-CQUJWQHSSA-N 0.000 claims description 3
- DLRVVLDZNNYCBX-RTPHMHGBSA-N isomaltose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)C(O)O1 DLRVVLDZNNYCBX-RTPHMHGBSA-N 0.000 claims description 3
- JCQLYHFGKNRPGE-FCVZTGTOSA-N lactulose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 JCQLYHFGKNRPGE-FCVZTGTOSA-N 0.000 claims description 3
- 229960000511 lactulose Drugs 0.000 claims description 3
- PFCRQPBOOFTZGQ-UHFFFAOYSA-N lactulose keto form Natural products OCC(=O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O PFCRQPBOOFTZGQ-UHFFFAOYSA-N 0.000 claims description 3
- JCQLYHFGKNRPGE-HFZVAGMNSA-N maltulose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JCQLYHFGKNRPGE-HFZVAGMNSA-N 0.000 claims description 3
- 150000002840 non-reducing disaccharides Chemical class 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 150000003267 reducing disaccharides Chemical class 0.000 claims description 3
- OVVGHDNPYGTYIT-BNXXONSGSA-N rutinose Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 OVVGHDNPYGTYIT-BNXXONSGSA-N 0.000 claims description 3
- PZDOWFGHCNHPQD-VNNZMYODSA-N sophorose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PZDOWFGHCNHPQD-VNNZMYODSA-N 0.000 claims description 3
- 229960004793 sucrose Drugs 0.000 claims description 3
- QIGJYVCQYDKYDW-UHFFFAOYSA-N 3-O-alpha-D-mannopyranosyl-D-mannopyranose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(CO)OC(O)C1O QIGJYVCQYDKYDW-UHFFFAOYSA-N 0.000 claims 1
- QIGJYVCQYDKYDW-LCOYTZNXSA-N laminarabiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1O QIGJYVCQYDKYDW-LCOYTZNXSA-N 0.000 claims 1
- 239000012038 nucleophile Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 150000004967 organic peroxy acids Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PVXPPJIGRGXGCY-TZLCEDOOSA-N 6-O-alpha-D-glucopyranosyl-D-fructofuranose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)C(O)(CO)O1 PVXPPJIGRGXGCY-TZLCEDOOSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 239000005913 Maltodextrin Substances 0.000 description 2
- 229920002774 Maltodextrin Polymers 0.000 description 2
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 230000000249 desinfective effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229940035034 maltodextrin Drugs 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- WTQMRYVXRLESSC-UHFFFAOYSA-N 2-(6-hydroxyhexan-3-yl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C(CCCO)CC)C(=O)C2=C1 WTQMRYVXRLESSC-UHFFFAOYSA-N 0.000 description 1
- UZJGVXSQDRSSHU-UHFFFAOYSA-N 6-(1,3-dioxoisoindol-2-yl)hexaneperoxoic acid Chemical compound C1=CC=C2C(=O)N(CCCCCC(=O)OO)C(=O)C2=C1 UZJGVXSQDRSSHU-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000003165 hydrotropic effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N peroxyacetic acid Substances CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002023 wood 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
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/221—Mono, di- or trisaccharides or derivatives thereof
-
- 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
- C11D3/3937—Stabilising agents
- C11D3/394—Organic 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
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3945—Organic per-compounds
Definitions
- the present invention relates to a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one disaccharide, to a detergent composition comprising said mixture, and to the use of at least one disaccharide for stabilizing a phthalimido percarboxylic acid in a detergent composition.
- organic peracids have encountered increasing interest in the industrial field, among others due to their excellent properties as bleaching agents in detergent formulations. Therefore, a large number of publications are concerned with organic peracid compounds endowed with the required property of sufficient bleaching activity, said characteristic being essential for an industrial application and a widespread use of such compounds.
- organic straight-chain or cyclic mono- or dipercarboxylic acids are known and used, e.g. in detergent compositions.
- boric acid As boric acid has become a chemical of high concern, it is to be expected that boric acid will be banned from use in domestic applications in the near future.
- the present invention satisfies this need by providing a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one disaccharide.
- a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one disaccharide.
- phthalimido percarboxylic acids can be stabilized by disaccharides. This is rather surprising since it was suggested by the prior art that phthalimido percarboxylic acids if not stabilized degrade following a radical reaction pathway.
- phthalimido peroxyhexanoic acid phthalimido percaproic acid, PAP
- PAP phthalimido percaproic acid
- nucleophilic reaction sites at PAP and/or by catching nucleophiles with electrophiles other than PAP.
- the present invention is directed to a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one disaccharide.
- the at least one disaccharide may be either a reducing or non- reducing disaccharide.
- the at least one disaccharide may be hydrous or anhydrous.
- the present invention also relates to the mixture described above, characterized in that it comprises at least one reducing disaccharide.
- the present invention further relates to the mixture described above, characterized in that it comprises at least one non-reducing disaccharide.
- Suitable disaccharides for use according to the present invention are cellobiose, gentiobiose, isomaltose, isomaltulose, lactose, lactulose, iaminaribiose, maltose, maltulose, melibiose, neohesperidose, neotrehalose, nigeriose, rutinose, sophorose, saccharose, and trehalose, wherein lactose represents the most preferred
- the present invention also relates to the mixture described above, characterized in that it comprises at least one disaccharide selected from the group consisting of cellobiose, gentiobiose, isomaltose, isomaltulose, lactose, lactulose, Iaminaribiose, maltose, maltulose, melibiose, neohesperidose, neotrehalose, nigeriose, rutinose, sophorose, saccharose, trehalose, and combinations thereof.
- the present invention further relates to the mixture as described above, characterized in that it comprises lactose.
- Suitable phthalimido percarboxylic acids for use according to the present invention may be selected from the phthalimido
- the present invention also relates to the mixture described above, characterized in that it comprises at least one phthalimido percarboxylic acid selected from the phthalimido percarboxylic acids of the general formula (I) above, where n is an integer of from 1 to 5.
- the present invention further relates to the mixture described above, characterized in that it comprises phthalimido percaproic acid.
- Phthalimido percarboxylic acids and especially phthalimido peroxycaproic acid may be prepared as described in EP 0 325 288 A1 and EP 0 349 940 B1 , respectively.
- a substrate selected from phthalimido carboxylic acids and anhydrides thereof having a structure corresponding to the desired percarboxylic acid e.g. of the general formula (I) may be reacted with concentrated H2O2 in a reaction medium selected from concentrated H 2 S0 4 and CH 3 SO 3 H or in an alkaline medium, and the
- percarboxylic acid is then separated from the reaction mixture by conventional and known techniques.
- the content of disaccharide in the mixture should range between 1 and 50 % by weight, preferably between 1 and 25 % by weight, more preferably between 1 and 10 % by weight, most preferably between 2 and 5 % by weight based on the total weight of the mixture.
- the present invention also relates to the mixture described above, characterized in that the content of disaccharide is between 1 and 50 % by weight, preferably between 1 and 25 % by weight, more preferably between 1 and 0 % by weight, most preferably between 2 and 5 % by weight based on the total weight of the mixture.
- the weight ratio of phthalimido percarboxylic acid to disaccharide is between 20:1 and 1 :1 , preferably between 10:1 and 1 :1 , more preferably between 5:1 and 1 :1 , most preferably between 2:1 and 1 :1.
- the present invention also relates to the mixture described above, characterized in that the weight ratio of phthalimido percarboxylic acid to
- disaccharide is between 20:1 and 1 :1 , preferably between 0:1 and 1 :1 , more preferably between 5:1 and 1 :1 , most preferably between 2:1 and 1 :1.
- An especially expedient mixture for use as a bleaching agent comprises between 10 and 25 % by weight of phthalimido peroxyhexanoic acid (phthalimido percaproic acid, PAP) and between 2 and 5 % by weight of lactose based on the total weight of the mixture. Therefore, the present invention also relates to the mixture described above, characterized in that it comprises between 10 and 25 % by weight of phthalimido peroxyhexanoic acid (phthalimido percaproic acid, PAP) and between 2 and 5 % by weight of lactose based on the total weight of the mixture.
- the mixture comprising the at least one phthalimido percarboxylic acid and the at least one disaccharide according to the present invention may be manufactured in the form of an aqueous solution, gel, emulsion, paste, dispersion, powder, flake, granules, scales, pearls, tablets, solid block form, extrudates and other forms known in the art, but preferably represents a powder or a flake.
- the present invention also relates to the mixture described above, characterized in that the mixture is in the form of a solid or a flake.
- the mixture according to the present invention is particularly suitable as effective bleaching agent in detergent formulations.
- the present invention also relates to the use of a mixture described above as a bleaching agent.
- the present invention further relates to a detergent composition
- a detergent composition comprising a mixture described above.
- the detergent composition may contain any additive or active ingredient commonly used in corresponding washing, cleansing and/or disinfecting agents like builders, surfactants, soaps, zeolites, hydrotropic agents, corrosion inhibitors, enzymes, optical brighteners, stabilizers, abrasives, perfumes, coloring agents.
- inventive mixture may be incorporated into the detergent composition either as such or in combination with further additives, for example phosphates, carbonates, zeolites, carboxymethylcellulose or filmbuilding agents like fatty acids, fatty acid amides or esters etc. in the forms mentioned above for the mixture.
- further additives for example phosphates, carbonates, zeolites, carboxymethylcellulose or filmbuilding agents like fatty acids, fatty acid amides or esters etc.
- the detergent composition is substantially free of boric acid, i.e. comprises less than 10 ppm, preferably less than 5 ppm, even more preferably less than 1 ppm, and most preferably less than 0,1 ppm boric acid. Therefore, the present invention aiso relates to the detergent composition described before, characterized in that it comprises less than 10 ppm, preferably less than 5 ppm, even more preferably less than 1 ppm, and most preferably less than 0,1 ppm boric acid.
- the detergent composition may be used as a laundry detergent, preferably as a textile detergent, and is not only suitable for generally washing laundry, but as well for disinfecting.
- the detergent according to the present application may be used as cleanser and/or disinfectant for cleansing and disinfecting various kinds of hard surfaces like, for example, in the medicinal or institutional field, in the food preparing, processing and/or selling industry, in agriculture, in hotel business, catering trade and/or in public buildings and/or institutions. It may as well be useful in further applications in which a disinfected surface is required or desired and which are not explicitly mentioned herein.
- the surfaces supposed to become disinfected may be made of common materials mentioned in the state of the art like, for example, metal, glass, ceramic, plastic, (coated) wood.
- the present invention relates to the use of at least one disaccharide for stabilizing a phthalimido percarboxylic acid in a detergent composition.
- a mixture for use as a bleaching agent comprising 86 % by weight of phthalimido peroxyhexanoic acid ⁇ phthalimido percaproic acid, PAP) and 14 % by weight of a stabilizing agent (example a: boric acid (comparative); example 1 b: glucose
- example 1d lactose
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Abstract
The present invention relates to a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one disaccharide, to a detergent composition comprising said mixture, and to the use of at least one disaccharide for stabilizing a phthalimido percarboxylic acid in a detergent composition.
Description
Stabilization of phthalimido percarboxylic acids with disaccharides
FIELD OF THE INVENTION
The present invention relates to a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one disaccharide, to a detergent composition comprising said mixture, and to the use of at least one disaccharide for stabilizing a phthalimido percarboxylic acid in a detergent composition.
BACKGROUND OF THE INVENTION
In the past, organic peracids have encountered increasing interest in the industrial field, among others due to their excellent properties as bleaching agents in detergent formulations. Therefore, a large number of publications are concerned with organic peracid compounds endowed with the required property of sufficient bleaching activity, said characteristic being essential for an industrial application and a widespread use of such compounds. Thus, many organic straight-chain or cyclic mono- or dipercarboxylic acids are known and used, e.g. in detergent compositions.
A problem with the widespread use of organic peracids arises from their low thermal stability, which makes it necessary to physically or chemically stabilize these compounds. The organic peracids known so far show a significant decrease of active oxygen, even under conventional storage conditions. This is also the case with imido percarboxylic acids as described already in J. Chem. Soc. 1962, 3821 and Chem. Ind. 1961 , 469. Among the imido percarboxylic acids, phthalimido percarboxylic acids have gained a widespread use in industry, especially as bleaching agents in detergent compositions. However, addition of boric acid to phthalimido percarboxylic acids is considered necessary to guarantee a sufficient long-term stability.
As boric acid has become a chemical of high concern, it is to be expected that boric acid will be banned from use in domestic applications in the near future.
Consequently, there is a need for alternative ways of stabilizing phthalimido percarboxylic acids in detergent compositions without making use of boric acid.
SUMMARY OF THE INVENTION
The present invention satisfies this need by providing a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one disaccharide. With the present invention, it is possible to stabilize phthalimido percarboxylic acids so as to minimize a decrease of oxygen under conventional storage conditions, but to avoid the use of boric acid. Thus, detergent compositions may be obtained showing sufficient bleaching activity over time.
DETAILED DESCRIPTION OF THE INVENTION
After extensive studies, the inventors have found that phthalimido percarboxylic acids can be stabilized by disaccharides. This is rather surprising since it was suggested by the prior art that phthalimido percarboxylic acids if not stabilized degrade following a radical reaction pathway.
Without wishing to be bound to any theory, it is assumed that phthalimido
percarboxylic acids in fact degrade by attack of nucleophiles. A plausible degradation scheme of phthalimido peroxyhexanoic acid (phthalimido percaproic acid, PAP) in alkaline conditions is shown in figure 1. According to figure 1 , PAP is degraded to 4- phthalimido-1-hexanol and carbon dioxide via an electrocyclic reaction. As a consequence, the presence of at least one disaccharide would prevent nucleophiles from degrading PAP either by excluding reactive nucleophiles, by blocking
nucleophilic reaction sites at PAP and/or by catching nucleophiles with electrophiles other than PAP.
Therefore, the present invention is directed to a mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one disaccharide.
There is no restriction as concerns the chemical nature of the at least one
disaccharide. Thus, the at least one disaccharide may be either a reducing or non- reducing disaccharide. Besides, the at least one disaccharide may be hydrous or anhydrous.
Therefore, the present invention also relates to the mixture described above, characterized in that it comprises at least one reducing disaccharide. The present
invention further relates to the mixture described above, characterized in that it comprises at least one non-reducing disaccharide.
Suitable disaccharides for use according to the present invention are cellobiose, gentiobiose, isomaltose, isomaltulose, lactose, lactulose, iaminaribiose, maltose, maltulose, melibiose, neohesperidose, neotrehalose, nigeriose, rutinose, sophorose, saccharose, and trehalose, wherein lactose represents the most preferred
disaccharide.
Therefore, the present invention also relates to the mixture described above, characterized in that it comprises at least one disaccharide selected from the group consisting of cellobiose, gentiobiose, isomaltose, isomaltulose, lactose, lactulose, Iaminaribiose, maltose, maltulose, melibiose, neohesperidose, neotrehalose, nigeriose, rutinose, sophorose, saccharose, trehalose, and combinations thereof. The present invention further relates to the mixture as described above, characterized in that it comprises lactose.
Also, there is no restriction as concerns the chemical nature of the at least one phthalimido percarboxylic acid. Suitable phthalimido percarboxylic acids for use according to the present invention may be selected from the phthalimido
percarboxylic acids of the general formula (I), where n is an integer of from 1 to 5:
Thus, suitable phthalimido percarboxylic acids for use according to the present invention may be selected from the group consisting of phthalimido peracetic acid (n=1), phthalimido perpropionic acid (n=2), phthalimido perbutyirc acid (n=3), phthalimido peramylic acid (n=4) and phthalimido percaproic acid (n=5), wherein phthalimido percaproic acid represents the most preferred phthalimido percarboxylic acid.
Therefore, the present invention also relates to the mixture described above, characterized in that it comprises at least one phthalimido percarboxylic acid selected from the phthalimido percarboxylic acids of the general formula (I) above, where n is
an integer of from 1 to 5. The present invention further relates to the mixture described above, characterized in that it comprises phthalimido percaproic acid.
Phthalimido percarboxylic acids and especially phthalimido peroxycaproic acid may be prepared as described in EP 0 325 288 A1 and EP 0 349 940 B1 , respectively. Thus, a substrate selected from phthalimido carboxylic acids and anhydrides thereof having a structure corresponding to the desired percarboxylic acid e.g. of the general formula (I) may be reacted with concentrated H2O2 in a reaction medium selected from concentrated H2S04 and CH3SO3H or in an alkaline medium, and the
percarboxylic acid is then separated from the reaction mixture by conventional and known techniques.
In order to obtain optimum stabilization of the at least one phthalimido percarboxylic acid, the content of disaccharide in the mixture should range between 1 and 50 % by weight, preferably between 1 and 25 % by weight, more preferably between 1 and 10 % by weight, most preferably between 2 and 5 % by weight based on the total weight of the mixture.
Therefore, the present invention also relates to the mixture described above, characterized in that the content of disaccharide is between 1 and 50 % by weight, preferably between 1 and 25 % by weight, more preferably between 1 and 0 % by weight, most preferably between 2 and 5 % by weight based on the total weight of the mixture.
Advantageously, the weight ratio of phthalimido percarboxylic acid to disaccharide is between 20:1 and 1 :1 , preferably between 10:1 and 1 :1 , more preferably between 5:1 and 1 :1 , most preferably between 2:1 and 1 :1.
Therefore, the present invention also relates to the mixture described above, characterized in that the weight ratio of phthalimido percarboxylic acid to
disaccharide is between 20:1 and 1 :1 , preferably between 0:1 and 1 :1 , more preferably between 5:1 and 1 :1 , most preferably between 2:1 and 1 :1.
An especially expedient mixture for use as a bleaching agent comprises between 10 and 25 % by weight of phthalimido peroxyhexanoic acid (phthalimido percaproic acid, PAP) and between 2 and 5 % by weight of lactose based on the total weight of the mixture.
Therefore, the present invention also relates to the mixture described above, characterized in that it comprises between 10 and 25 % by weight of phthalimido peroxyhexanoic acid (phthalimido percaproic acid, PAP) and between 2 and 5 % by weight of lactose based on the total weight of the mixture.
The mixture comprising the at least one phthalimido percarboxylic acid and the at least one disaccharide according to the present invention may be manufactured in the form of an aqueous solution, gel, emulsion, paste, dispersion, powder, flake, granules, scales, pearls, tablets, solid block form, extrudates and other forms known in the art, but preferably represents a powder or a flake.
Therefore, the present invention also relates to the mixture described above, characterized in that the mixture is in the form of a solid or a flake.
The mixture according to the present invention is particularly suitable as effective bleaching agent in detergent formulations.
Therefore, the present invention also relates to the use of a mixture described above as a bleaching agent.
The present invention further relates to a detergent composition comprising a mixture described above. The detergent composition may contain any additive or active ingredient commonly used in corresponding washing, cleansing and/or disinfecting agents like builders, surfactants, soaps, zeolites, hydrotropic agents, corrosion inhibitors, enzymes, optical brighteners, stabilizers, abrasives, perfumes, coloring agents.
The inventive mixture may be incorporated into the detergent composition either as such or in combination with further additives, for example phosphates, carbonates, zeolites, carboxymethylcellulose or filmbuilding agents like fatty acids, fatty acid amides or esters etc. in the forms mentioned above for the mixture.
In a preferred embodiment the detergent composition is substantially free of boric acid, i.e. comprises less than 10 ppm, preferably less than 5 ppm, even more preferably less than 1 ppm, and most preferably less than 0,1 ppm boric acid.
Therefore, the present invention aiso relates to the detergent composition described before, characterized in that it comprises less than 10 ppm, preferably less than 5 ppm, even more preferably less than 1 ppm, and most preferably less than 0,1 ppm boric acid.
The detergent composition may be used as a laundry detergent, preferably as a textile detergent, and is not only suitable for generally washing laundry, but as well for disinfecting.
Besides, the detergent according to the present application may be used as cleanser and/or disinfectant for cleansing and disinfecting various kinds of hard surfaces like, for example, in the medicinal or institutional field, in the food preparing, processing and/or selling industry, in agriculture, in hotel business, catering trade and/or in public buildings and/or institutions. It may as well be useful in further applications in which a disinfected surface is required or desired and which are not explicitly mentioned herein. The surfaces supposed to become disinfected may be made of common materials mentioned in the state of the art like, for example, metal, glass, ceramic, plastic, (coated) wood.
Finally, the present invention relates to the use of at least one disaccharide for stabilizing a phthalimido percarboxylic acid in a detergent composition.
In the following, the stabilization of phthalimido peroxycarboxylic acids with disaccharides will be demonstrated without being restricted to these examples.
EXAMPLES
Example 1 :
A mixture for use as a bleaching agent comprising 86 % by weight of phthalimido peroxyhexanoic acid {phthalimido percaproic acid, PAP) and 14 % by weight of a stabilizing agent (example a: boric acid (comparative); example 1 b: glucose
(comparative); example 1c: maltodextrin (comparative); example 1d: lactose) was tested for its long-term stability. Therefore, the amount of chemically active PAP in the respective mixture was determined after storage by 40 °C at 1 , 3, 7, 14, 21 , 28, 49, 84, 1 9, 161 and 2 0 days, respectively.
As can be taken from Table 1 , a mixture comprising lactose (example 1d) shows a significantly higher long-term stability of phthalimido peroxyhexanoic acid
(phthalimido percaproic acid, PAP) than a mixture comprising glucose (example 1 b) or maltodextrin (example 1 c).
Table 1 :
Moreover, as can be taken from Figure 2, phthalimido peroxyhexanoic acid
(phthalimido percaproic acid, PAP) can even more effectively be stabilized by a disaccharide according to the present invention (example 1d) than by boric acid conventionally used (example 1a).
Claims
1. Mixture for use as a bleaching agent comprising at least one phthalimido percarboxylic acid and at least one disaccharide.
2. Mixture according to claim 1 , characterized in that it comprises at least one reducing disaccharide.
3. Mixture according to claim 1 or 2, characterized in that it comprises at least one a non-reducing disaccharide.
4. Mixture according to any of claims 1 to 3, characterized in that it comprises at least one disaccharide selected from the group consisting of cellobiose, gentiobiose, isomaltose, isomaltuiose, lactose, lactulose, laminaribiose, maltose, maltulose, melibiose, neohesperidose, neotrehalose, nigeriose, rutinose, sophorose, saccharose, trehalose, and combinations thereof.
5. Mixture according to any of claims 1 to 4, characterized in that it comprises lactose.
6. Mixture according to any of claims 1 to 5, characterized in that it comprises at least one phthalimido percarboxylic acid selected from the phthalimido percarboxylic acids of the general formula (I)
where n is an integer of from 1 to 5.
7. Mixture according to any of claims 1 to 6, characterized in that it comprises phthalimido peroxyhexanoic acid.
8. ixture according to any of claims 1 to 7, characterized in that the content of disaccharide is between 1 and 50 % by weight, preferably between 1 and 25 % by weight, more preferably between 1 and 10 % by weight, most preferably between 2 and 5 % by weight based on the total weight of the mixture.
9. Mixture according to any of ciaims 1 to 8, characterized in that the weight ratio of phthalimido percarboxylic acid to disaccharide is between 20:1 and 1 :1 , preferably between 10:1 and 1 :1 , more preferably between 5:1 and 1 :1 , most preferably between 2:1 and 1 :1.
10. Mixture according to any of claims 1 to 9, characterized in that it comprises between 10 and 25 % by weight of phthalimido peroxyhexanoic acid
(phthalimido percaproic acid, PAP) and between 2 and 5 % by weight of lactose based on the total weight of the mixture.
11.Mixture according to any of claims 1 to 10, characterized in that the mixture is in the form of a powder or a flake.
12. Use of a mixture according to any of claims 1 to 11 as a bleaching agent.
13. Detergent composition comprising the mixture according to any of claims 1 to 11.
14. Detergent composition according to claim 13, characterized in that it
comprises less than 10 ppm, preferably less than 5 ppm, even more preferably less than 1 ppm, most preferably less than 0,1 ppm boric acid.
15. Use of at least one disaccharide for stabilizing a phthalimido percarboxylic acid in a detergent composition.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2012/060449 WO2013178290A1 (en) | 2012-06-01 | 2012-06-01 | Stabilization of phthalimido percarboxylic acids with disaccharides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2855654A1 true EP2855654A1 (en) | 2015-04-08 |
Family
ID=46229472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP12726408.3A Withdrawn EP2855654A1 (en) | 2012-06-01 | 2012-06-01 | Stabilization of phthalimido percarboxylic acids with disaccharides |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP2855654A1 (en) |
| WO (1) | WO2013178290A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201402257D0 (en) * | 2014-02-10 | 2014-03-26 | Revolymer Ltd | Novel Peracid - containing particle |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1233846B (en) | 1988-01-20 | 1992-04-21 | Ausimont Spa | IMMEDIATE AROMATIC PEROXIDES |
| DE3823172C2 (en) | 1988-07-08 | 1998-01-22 | Hoechst Ag | Omega-phthalimidoperoxihexanoic acid, process for its preparation and its use |
| GB0509377D0 (en) * | 2005-05-09 | 2005-06-15 | Reckitt Benckiser Nv | Detergent composition |
| EP1760141A1 (en) * | 2005-09-06 | 2007-03-07 | SOLVAY (Société Anonyme) | Coated peroxycarboxylic acid granules, process for their preparation and their use in detergent, bleach or disinfection applications |
| GB201019628D0 (en) * | 2010-11-19 | 2010-12-29 | Reckitt Benckiser Nv | Dyed coated bleach materials |
-
2012
- 2012-06-01 EP EP12726408.3A patent/EP2855654A1/en not_active Withdrawn
- 2012-06-01 WO PCT/EP2012/060449 patent/WO2013178290A1/en not_active Ceased
Non-Patent Citations (2)
| Title |
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| None * |
| See also references of WO2013178290A1 * |
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| WO2013178290A1 (en) | 2013-12-05 |
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