US3901819A - Compositions for activating an inorganic peroxide bleaching agent - Google Patents
Compositions for activating an inorganic peroxide bleaching agent Download PDFInfo
- Publication number
- US3901819A US3901819A US395264A US39526473A US3901819A US 3901819 A US3901819 A US 3901819A US 395264 A US395264 A US 395264A US 39526473 A US39526473 A US 39526473A US 3901819 A US3901819 A US 3901819A
- Authority
- US
- United States
- Prior art keywords
- acetic acid
- activating
- group
- ingredient
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 230000003213 activating effect Effects 0.000 title claims abstract description 29
- 239000007844 bleaching agent Substances 0.000 title claims abstract description 18
- 150000002978 peroxides Chemical class 0.000 title claims abstract description 17
- 150000002168 ethanoic acid esters Chemical class 0.000 claims abstract description 23
- 150000005846 sugar alcohols Chemical class 0.000 claims abstract description 23
- 239000004386 Erythritol Substances 0.000 claims abstract description 7
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 7
- 235000019414 erythritol Nutrition 0.000 claims abstract description 7
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims abstract description 7
- 229940009714 erythritol Drugs 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 238000002844 melting Methods 0.000 claims abstract description 7
- 230000008018 melting Effects 0.000 claims abstract description 7
- 150000002016 disaccharides Chemical class 0.000 claims abstract description 5
- 150000002772 monosaccharides Chemical class 0.000 claims abstract description 5
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 20
- 238000004061 bleaching Methods 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 239000001087 glyceryl triacetate Substances 0.000 claims description 9
- 235000013773 glyceryl triacetate Nutrition 0.000 claims description 9
- 239000004615 ingredient Substances 0.000 claims description 9
- 229960002622 triacetin Drugs 0.000 claims description 9
- UAOKXEHOENRFMP-ZJIFWQFVSA-N [(2r,3r,4s,5r)-2,3,4,5-tetraacetyloxy-6-oxohexyl] acetate Chemical compound CC(=O)OC[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)C=O UAOKXEHOENRFMP-ZJIFWQFVSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 6
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 6
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 6
- JNYAEWCLZODPBN-KVTDHHQDSA-N (2r,3r,4r)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@@H](O)[C@H]1O JNYAEWCLZODPBN-KVTDHHQDSA-N 0.000 claims description 5
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 5
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 claims description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 5
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 5
- 229930091371 Fructose Natural products 0.000 claims description 5
- 239000005715 Fructose Substances 0.000 claims description 5
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 5
- 229930195725 Mannitol Natural products 0.000 claims description 5
- 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 5
- 229930006000 Sucrose Natural products 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000000594 mannitol Substances 0.000 claims description 5
- 235000010355 mannitol Nutrition 0.000 claims description 5
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 claims description 5
- 239000000600 sorbitol Substances 0.000 claims description 5
- 239000005720 sucrose Substances 0.000 claims description 5
- 229940022860 xylitan Drugs 0.000 claims description 5
- 229960001922 sodium perborate Drugs 0.000 claims description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 3
- 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
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 3
- 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 claims description 3
- 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 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
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 3
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-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
- 229940105990 diglycerin Drugs 0.000 claims description 3
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 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
- 229930182830 galactose Natural products 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 229960002163 hydrogen peroxide Drugs 0.000 claims description 3
- 239000008101 lactose Substances 0.000 claims description 3
- 229940045872 sodium percarbonate Drugs 0.000 claims description 3
- WODGXFMUOLGZSY-UHFFFAOYSA-J tetrasodium phosphonatooxy phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OOP([O-])([O-])=O WODGXFMUOLGZSY-UHFFFAOYSA-J 0.000 claims description 3
- KJFGIEUERFWKMN-UHFFFAOYSA-M tetrasodium trioxido(oxidooxy)silane Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]O[Si]([O-])([O-])[O-] KJFGIEUERFWKMN-UHFFFAOYSA-M 0.000 claims description 3
- 239000000811 xylitol Substances 0.000 claims description 3
- 235000010447 xylitol Nutrition 0.000 claims description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 3
- 229960002675 xylitol Drugs 0.000 claims description 3
- NVKPIAUSOPISJK-YIONKMFJSA-N [(2r,4s)-2,3,4,5-tetraacetyloxypentyl] acetate Chemical compound CC(=O)OC[C@@H](OC(C)=O)C(OC(C)=O)[C@@H](OC(C)=O)COC(C)=O NVKPIAUSOPISJK-YIONKMFJSA-N 0.000 claims description 2
- JUVKBTMTRQITRH-VWFNIEHNSA-N acetic acid (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O JUVKBTMTRQITRH-VWFNIEHNSA-N 0.000 claims description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 125000004185 ester group Chemical group 0.000 abstract description 4
- 230000000694 effects Effects 0.000 description 7
- 239000000843 powder Substances 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 description 3
- 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 3
- 239000004744 fabric Substances 0.000 description 3
- 238000002310 reflectometry Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 150000001875 compounds Chemical class 0.000 description 2
- -1 i.e. Chemical compound 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 235000019832 sodium triphosphate Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 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
- 239000002738 chelating agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 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
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material 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
- C11D3/391—Oxygen-containing 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
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3905—Bleach activators or bleach catalysts
- C11D3/3907—Organic compounds
- C11D3/391—Oxygen-containing compounds
- C11D3/3912—Oxygen-containing compounds derived from saccharides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
- D06L4/12—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen combined with specific additives
Definitions
- acetic acid esters of sugars and sugar alcohols As conventional activating agents meeting these re quirements, there can be mentioned acetic acid esters of sugars and sugar alcohols. In these acetic acid esters, a sufficient effect cannot be obtained by partially ester ified compounds, and hence, all of the hydroxyl groups should be esterified with acetic acid.
- This invention provides a composition for activating an inorganic peroxide bleaching agent which consists essentially of (A) an acetic acid ester of a monosaccharide, a disaccharide, a sugar alcohol, an internal anhydride of a sugar alcohol, or erythritol, and mixtures thereof. said ester having at least 2 ester groups on the adjacent carbon atoms, and (B) an acetic acid ester of a polyhydric alcohol having a melting point not higher than 30C., the weight ratio of A:B being within the range of from l:9 to 9:l, preferably 1:3 to 3:1, espe cially about l:l.
- Acetic acid esters of monosaccharides, disaccharides, sugar alcohols, internal anhydrides of sugar alcohols and erythritol employed in this invention include acetic acid esters of hexoses such as glucose, mannose, galactose and fructose; pentoses such as arabinose and xylose', disaccharides such as sucrose, lactose and maltose', hexitols such as sorbitol and mannitol; internal anhydrides of hexitols, i.e., hexitan, such as sorbitan and mannitan; pentitols such as xylitol and arabitol', internal anhydrides of pentitols, i.e., pentitans, such as xylitan; and the like. These acetic acid esters should have at least 2 ester groups on adjacent carbon atoms and they can be up to 100% esterified.
- acetic acid esters are glucose pentacetate, glucose tetracetate, fructose pentacetate, sucrose octacetate, sorbitol hexacetate, sorbitan tetracetate, mannitol hexacetate, mannitan tetracetate, xylitol pentacetate, xylitan triacetate and erythritol tetracetate.
- Acetic acid esters of polyhydric alcohols having a melting point not higher than 30C. which are used in the composition of this invention, include acetic acid esters of ethylene glycol, propylene glycol, butylene glycol, glycerin and diglycerin.
- esters have a degree of esterification of Glycerine triacetate, i.e., triacetin, and ethylene glycol diacetate are especially preferred, because they have an activity of activating an inorganic peroxide bleaching agent.
- Tetracetyl ethylenediamine is an activating agent of low water solubility, like the acetic acid esters of sugars and sugar alcohols employed in this invention. But in this case of tetracetyl ethylenediamine, an improved effect cannot be obtained by mixing it with, for example, triacetin.
- the specific synergistic effects of 1 improving the water solubility and (2) enhancing the activating property, that characterize the composition of this invention, can be attained only by employing a combination of an acetic acid ester of a sugar or sugar alcohol etc. as set forth above and an acetic acid ester of a polyhydric alcohol having a melting point not higher than 30C.
- the activating composition of this invention can be directly added to a bleaching liquor containing an inorganic peroxide, or it can be incorporated in advance into an inorganic peroxide bleaching agent. In the latter case, the composition can be kneaded with a granulating agent such as polyethylene glycol 6000 and formed into granules having flowability.
- a granulating agent such as polyethylene glycol 6000
- composition may further comprise surfactants such as anionic surfac tants, non-ionic surfactants and amphoteric surfactants, neutral inorganic salts such as sodium sulfate, alkaline inorganic salts such as sodium tripolyphosphate, heavy metal chelating agents such as sodium nitrilotriacetate, redeposition-preventive agents such as carboxymethyl cellulose, perfumes, fluorescent dyes, and the like.
- surfactants such as anionic surfac tants, non-ionic surfactants and amphoteric surfactants, neutral inorganic salts such as sodium sulfate, alkaline inorganic salts such as sodium tripolyphosphate, heavy metal chelating agents such as sodium nitrilotriacetate, redeposition-preventive agents such as carboxymethyl cellulose, perfumes, fluorescent dyes, and the like.
- Inorganic peroxide bleaching agents to which the composition of this invention can be applied are sub stances capable of releasing hydrogen peroxide in an aqueous solution.
- bleaching agents are hydrogen peroxide, sodium perborate, sodium percarbonate, sodium peroxypyrophosphate and sodium peroxysilicate.
- the mixing ratio of the activating composition of this invention to the inorganic peroxide is within the range of from l/9 to 9/1 on the weight basis.
- the proportion of the activating composition is increased. It is also preferred that when the bleaching agent is used at a relatively high temperature for a long time, the proportion of the activating composition is reduced.
- EXAMPLE I The activating agents listed in the following Table l ere respectively added in an amount of 0.5 part to parts of a aqueous solution of sodium perboate. The state of dissolution of the activating agent was xamined after the mixture had been allowed to stand till at 20C. for 1 minute. Then a bleaching test was onducted at 20C. for minutes. The results oblined are shown in the following Table 1.
- the bleaching test was carried out as follows: Three )i1ed cloths for the bleaching test (cloth of 10 cm X 7 m soiled with tea) were put into a Terg-O-Tometer nd subjected to rotating agitation at 100 rpm, at C )r 10 minutes. The cloths were then rinsed with city ater, air-dried and ironed.
- compositions were determined by leasuring the reflectivities of the cloths before and fter the treatment.
- the bleaching force is expressed in :rms of the value of reflectivity of bleached cloth) (reflectivity of untreated cloth)).
- EXAMPLE 2 In each test, 0.5 part of an activating agent listed in e following Table 2 was added to 100 parts of a caching agent aqueous solution containing 1.0% of dium percarbonate, 0.05% of sodium dodecylbennesulfonate and 1.0% of sodium tripolyphosphate. 1e bleaching test was conducted in the same manner in Example 1 and the results shown in the following ible 2 were obtained.
- An activating agent composition for activating an inorganic peroxide bleaching agent consisting essentially of A. acetic acid ester of a substance selected from the group consisting of a monosaccharide, a disaccha- From the above results, it is seen that a mixture of rbitol hexacctate and ethylene glycol diacetate ex ride, a sugar alcohol, an internal anhydride of a sugar alcohol, erythritol and mixtures thereof, said ester having at least two ester groups on adjacent carbon atoms of said substance, and
- acetic acid ester of polyhydric alcohol having a melting point not higher than about 30C, the weight ratio of A18 being from 1:9 to 9:1.
- ingredient A is an acetic acid ester of substance selected from the group consisting of glucose, mannose, galactose, fructose, arabinose, xylose, sucrose, lactose, maltose, sorbitol, mannitol, sorbitan, mannitan, xylitol, arabitol, and xylitan and mixtures thereof.
- ingredient A is selected from the group consisting of glucose pentacetate, glucose tetracetate, fructose pentacetate, sucrose octacetate, sorbitol hexacetate, sorbitan tetracetate, mannitol hexacetate, mannitan tetracetate, xylitol pentacetate, xylitan triacetate and erythritol tetracetate.
- ingredient B is selected from the group consisting of triacetin and ethylene glycol diacetate.
- a bleaching composition comprising (1) an inorganic peroxide bleaching agent capable of releasing hydrogen peroxide in an aqueous solution, and (2) an activating agent composition as defined in claim 1, in which the weight ratio of l ):(2) is from 1:9 to 9:1.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47092265A JPS526867B2 (en)) | 1972-09-14 | 1972-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3901819A true US3901819A (en) | 1975-08-26 |
Family
ID=14049556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US395264A Expired - Lifetime US3901819A (en) | 1972-09-14 | 1973-09-07 | Compositions for activating an inorganic peroxide bleaching agent |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3901819A (en)) |
| JP (1) | JPS526867B2 (en)) |
| DE (1) | DE2344990C3 (en)) |
| FR (1) | FR2200397B1 (en)) |
Cited By (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4457858A (en) * | 1981-07-17 | 1984-07-03 | Henkel Kommanditgesellschaft Auf Aktien | Method of making coated granular bleach activators by spray drying |
| US5151212A (en) * | 1990-03-21 | 1992-09-29 | The Belzak Corporation | Peroxygen compound activation |
| US5342542A (en) * | 1990-12-28 | 1994-08-30 | Ausimont S.P.A. | Process for increasing the bleaching efficiency of persalts by using a partially acetylated sucrose as a bleach activator |
| US5344581A (en) * | 1991-07-31 | 1994-09-06 | Ausimont S.P.A. | Process for increasing the bleaching efficiency of an inorganic persalt using an acetylated mixture of sorbital and mammitol |
| US5360573A (en) * | 1991-08-06 | 1994-11-01 | Lever Brothers Company, Division Of Conopco, Inc. | Bleach precursors |
| US5401435A (en) * | 1991-06-10 | 1995-03-28 | Ausimont S.P.A. | Process for increasing the bleaching efficiency of an inorganic persalt or of hydrogen peroxide |
| WO1995008509A1 (en) * | 1993-09-21 | 1995-03-30 | The Procter & Gamble Company | Granular laundry bleaching composition |
| US5431849A (en) * | 1989-01-23 | 1995-07-11 | Novo Nordisk A/S | Bleaching detergent composition containing acylated sugar bleach activators |
| US5663132A (en) * | 1995-03-01 | 1997-09-02 | Charvid Limited Liability Company | Non-caustic composition comprising peroxygen compound and metasilicate and cleaning methods for using same |
| US5688757A (en) * | 1990-01-22 | 1997-11-18 | Novo Nordisk A/S The Procter & Gamble Co. | Sugar derivatives containing both long and short chain acyl groups as bleach activators |
| US5898024A (en) * | 1995-03-01 | 1999-04-27 | Charvid Limited Liability | Non-caustic cleaning composition comprising peroxygen compound and specific silicate, and method of making the same in free-flowing, particulate form |
| US6020295A (en) * | 1995-05-06 | 2000-02-01 | Solvay Interox Limited | Detergent builders/activators derived from the oxidation and acylation of polysaccharides |
| US6034048A (en) * | 1995-03-01 | 2000-03-07 | Charvid Limited Liability Co. | Non-caustic cleaning composition using an alkali salt |
| US6194367B1 (en) | 1995-03-01 | 2001-02-27 | Charvid Limited Liability Co. | Non-caustic cleaning composition comprising peroxygen compound and specific silicate and method of making the same in free-flowing, particulate form |
| US6221341B1 (en) * | 1997-11-19 | 2001-04-24 | Oraceutical Llc | Tooth whitening compositions |
| US6419905B1 (en) * | 1998-03-20 | 2002-07-16 | Biocosmetics, S.L. | Tooth whitening composition |
| WO2003028429A2 (en) | 2001-10-01 | 2003-04-10 | Sandia Corporation | Enhanced formulations for neutralization of chemical, biological and industrial toxants |
| US20030158459A1 (en) * | 1998-06-30 | 2003-08-21 | Tucker Mark D. | Enhanced formulations for neutraliztion of chemical, biological and industrial toxants |
| US20030198605A1 (en) * | 1998-02-13 | 2003-10-23 | Montgomery R. Eric | Light-activated tooth whitening composition and method of using same |
| US20040022867A1 (en) * | 2002-07-19 | 2004-02-05 | Tucker Mark D. | Decontamination formulation with sorbent additive |
| US20050109981A1 (en) * | 2000-06-29 | 2005-05-26 | Tucker Mark D. | Decontamination formulations for disinfection and sterilization |
| US20050265933A1 (en) * | 1998-02-13 | 2005-12-01 | Montgomery Robert E | Light-activated tooth whitening method |
| US7125497B1 (en) * | 2003-05-22 | 2006-10-24 | Sandia Corporation | Reactive formulations for a neutralization of toxic industrial chemicals |
| US7276468B1 (en) * | 1998-06-30 | 2007-10-02 | Sandia Corporation | Granulated decontamination formulations |
| US7662759B1 (en) * | 2005-01-28 | 2010-02-16 | Sandia Corporation | Decontamination formulation with additive for enhanced mold remediation |
| US20100056404A1 (en) * | 2008-08-29 | 2010-03-04 | Micro Pure Solutions, Llc | Method for treating hydrogen sulfide-containing fluids |
| US8652455B2 (en) | 2010-12-20 | 2014-02-18 | E I Du Pont De Nemours And Company | Targeted perhydrolases |
| US8663616B2 (en) | 2010-12-20 | 2014-03-04 | E I Du Pont De Nemours And Company | Enzymatic peracid generation for use in oral care products |
| US20140116960A1 (en) * | 2011-06-24 | 2014-05-01 | Washington State University Research Foundation | Oxidation of contaminants |
| US9409216B1 (en) | 2008-05-12 | 2016-08-09 | Oxytec Llc | Chemical oxidation method and compounds |
| US11607033B2 (en) | 2019-01-22 | 2023-03-21 | Colgate-Palmolive Company | Whitening system |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5230795A (en) * | 1975-09-04 | 1977-03-08 | Kao Corp | Composition for bleaching agent |
| JPH0699716B2 (ja) * | 1985-08-14 | 1994-12-07 | 花王株式会社 | 固体表面用漂白剤組成物 |
| US4800038A (en) * | 1988-01-21 | 1989-01-24 | Colgate-Palmolive Company | Acetylated sugar ethers as bleach activators detergency boosters and fabric softeners |
| EP0447553B1 (en) * | 1989-09-11 | 1996-06-12 | Kao Corporation | Bleaching composition |
| JP3431706B2 (ja) * | 1994-12-16 | 2003-07-28 | 新日本石油化学株式会社 | 積層体・不織布または織布並びにそれらを用いた強化積層体 |
| US6054086A (en) * | 1995-03-24 | 2000-04-25 | Nippon Petrochemicals Co., Ltd. | Process of making high-strength yarns |
| DE102006039841A1 (de) * | 2006-08-25 | 2008-02-28 | Henkel Kgaa | Aufhell- und/oder Färbemittel mit Polyolestern |
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|---|---|---|---|---|
| US3163606A (en) * | 1959-06-19 | 1964-12-29 | Konink Ind Mij Vorheen Noury & | Textile bleaching composition |
| US3211658A (en) * | 1961-03-24 | 1965-10-12 | Colgate Palmolive Co | Detergent composition with improved bleaching efficiency |
| US3338839A (en) * | 1964-12-28 | 1967-08-29 | Fmc Corp | Activating of peroxygen compounds |
| US3650962A (en) * | 1968-12-21 | 1972-03-21 | Henkel & Cie Gmbh | Washing bleaching and cleansing agents containing poly-(n-acetic acid)-ethyleneimines |
| US3661789A (en) * | 1969-07-22 | 1972-05-09 | American Home Prod | Stabilized oxygen bleach-activator system |
| US3840466A (en) * | 1968-03-07 | 1974-10-08 | Colgate Palmolive Co | Stain removal |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL113890C (en)) * | 1955-07-27 |
-
1972
- 1972-09-14 JP JP47092265A patent/JPS526867B2/ja not_active Expired
-
1973
- 1973-09-06 DE DE2344990A patent/DE2344990C3/de not_active Expired
- 1973-09-07 US US395264A patent/US3901819A/en not_active Expired - Lifetime
- 1973-09-14 FR FR7333036A patent/FR2200397B1/fr not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3163606A (en) * | 1959-06-19 | 1964-12-29 | Konink Ind Mij Vorheen Noury & | Textile bleaching composition |
| US3211658A (en) * | 1961-03-24 | 1965-10-12 | Colgate Palmolive Co | Detergent composition with improved bleaching efficiency |
| US3338839A (en) * | 1964-12-28 | 1967-08-29 | Fmc Corp | Activating of peroxygen compounds |
| US3840466A (en) * | 1968-03-07 | 1974-10-08 | Colgate Palmolive Co | Stain removal |
| US3650962A (en) * | 1968-12-21 | 1972-03-21 | Henkel & Cie Gmbh | Washing bleaching and cleansing agents containing poly-(n-acetic acid)-ethyleneimines |
| US3661789A (en) * | 1969-07-22 | 1972-05-09 | American Home Prod | Stabilized oxygen bleach-activator system |
Cited By (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4457858A (en) * | 1981-07-17 | 1984-07-03 | Henkel Kommanditgesellschaft Auf Aktien | Method of making coated granular bleach activators by spray drying |
| US5431849A (en) * | 1989-01-23 | 1995-07-11 | Novo Nordisk A/S | Bleaching detergent composition containing acylated sugar bleach activators |
| US5688757A (en) * | 1990-01-22 | 1997-11-18 | Novo Nordisk A/S The Procter & Gamble Co. | Sugar derivatives containing both long and short chain acyl groups as bleach activators |
| US5151212A (en) * | 1990-03-21 | 1992-09-29 | The Belzak Corporation | Peroxygen compound activation |
| EP0448337B1 (en) * | 1990-03-21 | 1995-06-21 | The Belzak Corporation | Peroxygen compound activation |
| US5342542A (en) * | 1990-12-28 | 1994-08-30 | Ausimont S.P.A. | Process for increasing the bleaching efficiency of persalts by using a partially acetylated sucrose as a bleach activator |
| US5401435A (en) * | 1991-06-10 | 1995-03-28 | Ausimont S.P.A. | Process for increasing the bleaching efficiency of an inorganic persalt or of hydrogen peroxide |
| US5344581A (en) * | 1991-07-31 | 1994-09-06 | Ausimont S.P.A. | Process for increasing the bleaching efficiency of an inorganic persalt using an acetylated mixture of sorbital and mammitol |
| US5360573A (en) * | 1991-08-06 | 1994-11-01 | Lever Brothers Company, Division Of Conopco, Inc. | Bleach precursors |
| WO1995008509A1 (en) * | 1993-09-21 | 1995-03-30 | The Procter & Gamble Company | Granular laundry bleaching composition |
| US5702635A (en) * | 1993-09-21 | 1997-12-30 | The Procter & Gamble Company | Granular laundry bleaching composition |
| CN1038028C (zh) * | 1993-09-21 | 1998-04-15 | 普罗格特-甘布尔公司 | 粒状洗衣漂白合剂 |
| US5663132A (en) * | 1995-03-01 | 1997-09-02 | Charvid Limited Liability Company | Non-caustic composition comprising peroxygen compound and metasilicate and cleaning methods for using same |
| US5789361A (en) * | 1995-03-01 | 1998-08-04 | Charvid Limited Liability Co. | Non-caustic cleaning composition comprising peroxygen compound and specific silicate, and method of making same in free-flowing, particulate form |
| US5863345A (en) * | 1995-03-01 | 1999-01-26 | Charvid Limited Liability Company | Methods for removing foreign deposits from hard surfaces using non-caustic cleaning composition comprising peroxygen compound and specific silicate |
| US5898024A (en) * | 1995-03-01 | 1999-04-27 | Charvid Limited Liability | Non-caustic cleaning composition comprising peroxygen compound and specific silicate, and method of making the same in free-flowing, particulate form |
| US6194367B1 (en) | 1995-03-01 | 2001-02-27 | Charvid Limited Liability Co. | Non-caustic cleaning composition comprising peroxygen compound and specific silicate and method of making the same in free-flowing, particulate form |
| US6034048A (en) * | 1995-03-01 | 2000-03-07 | Charvid Limited Liability Co. | Non-caustic cleaning composition using an alkali salt |
| US6043207A (en) * | 1995-03-01 | 2000-03-28 | Charvid Limited Liability Co. | Non-caustic cleaning composition comprising peroxygen compound, meta/sesqui-silicate, chelate and method of making same in free-flowing, particulate form |
| US6020295A (en) * | 1995-05-06 | 2000-02-01 | Solvay Interox Limited | Detergent builders/activators derived from the oxidation and acylation of polysaccharides |
| US20040101497A1 (en) * | 1997-11-19 | 2004-05-27 | Britesmile Development, Inc. | Tooth whitening compositions |
| US6221341B1 (en) * | 1997-11-19 | 2001-04-24 | Oraceutical Llc | Tooth whitening compositions |
| US7189385B2 (en) * | 1997-11-19 | 2007-03-13 | Discus Dental Impressions, Inc. | Tooth whitening compositions |
| US8562955B2 (en) | 1998-02-13 | 2013-10-22 | Discus Dental, Llc | Light-activated tooth whitening method |
| US20030198605A1 (en) * | 1998-02-13 | 2003-10-23 | Montgomery R. Eric | Light-activated tooth whitening composition and method of using same |
| US20050265933A1 (en) * | 1998-02-13 | 2005-12-01 | Montgomery Robert E | Light-activated tooth whitening method |
| US6419905B1 (en) * | 1998-03-20 | 2002-07-16 | Biocosmetics, S.L. | Tooth whitening composition |
| US20030158459A1 (en) * | 1998-06-30 | 2003-08-21 | Tucker Mark D. | Enhanced formulations for neutraliztion of chemical, biological and industrial toxants |
| US7390432B2 (en) * | 1998-06-30 | 2008-06-24 | Sandia Corporation | Enhanced formulations for neutralization of chemical, biological and industrial toxants |
| US20070249509A1 (en) * | 1998-06-30 | 2007-10-25 | Tucker Mark D | Granulated decontamination formulations |
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| US20050109981A1 (en) * | 2000-06-29 | 2005-05-26 | Tucker Mark D. | Decontamination formulations for disinfection and sterilization |
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| WO2003028429A3 (en) * | 2001-10-01 | 2003-12-18 | Sandia Corp | Enhanced formulations for neutralization of chemical, biological and industrial toxants |
| EA009242B1 (ru) * | 2001-10-01 | 2007-12-28 | Сэндиа Корпорейшн | Улучшенные композиции для нейтрализации химических, биологических и промышленных токсических веществ |
| WO2003028429A2 (en) | 2001-10-01 | 2003-04-10 | Sandia Corporation | Enhanced formulations for neutralization of chemical, biological and industrial toxants |
| EP1434625A4 (en) * | 2001-10-01 | 2010-07-21 | Sandia Corp | ENHANCED FORMULATIONS FOR NEUTRALIZING CHEMICAL, BIOLOGICAL AND INDUSTRIAL TOXIC SUBSTANCES |
| US20040022867A1 (en) * | 2002-07-19 | 2004-02-05 | Tucker Mark D. | Decontamination formulation with sorbent additive |
| US7282470B2 (en) * | 2002-07-19 | 2007-10-16 | Sandia Corporation | Decontamination formulation with sorbent additive |
| US7125497B1 (en) * | 2003-05-22 | 2006-10-24 | Sandia Corporation | Reactive formulations for a neutralization of toxic industrial chemicals |
| WO2005089100A3 (en) * | 2004-01-27 | 2006-02-02 | Sandia Corp | Decontamination formulations for disinfection and sterilization |
| US7662759B1 (en) * | 2005-01-28 | 2010-02-16 | Sandia Corporation | Decontamination formulation with additive for enhanced mold remediation |
| US9409216B1 (en) | 2008-05-12 | 2016-08-09 | Oxytec Llc | Chemical oxidation method and compounds |
| US10183317B2 (en) | 2008-05-12 | 2019-01-22 | Oxytec Llc | Chemical oxidation method and compounds |
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| US20100056404A1 (en) * | 2008-08-29 | 2010-03-04 | Micro Pure Solutions, Llc | Method for treating hydrogen sulfide-containing fluids |
| US8652455B2 (en) | 2010-12-20 | 2014-02-18 | E I Du Pont De Nemours And Company | Targeted perhydrolases |
| US8663616B2 (en) | 2010-12-20 | 2014-03-04 | E I Du Pont De Nemours And Company | Enzymatic peracid generation for use in oral care products |
| US8815550B2 (en) | 2010-12-20 | 2014-08-26 | E I Du Pont De Nemours And Company | Targeted perhydrolases |
| US20140116960A1 (en) * | 2011-06-24 | 2014-05-01 | Washington State University Research Foundation | Oxidation of contaminants |
| US9616472B2 (en) * | 2011-06-24 | 2017-04-11 | Washington State University | Oxidation of contaminants |
| US11607033B2 (en) | 2019-01-22 | 2023-03-21 | Colgate-Palmolive Company | Whitening system |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS526867B2 (en)) | 1977-02-25 |
| DE2344990B2 (de) | 1981-01-08 |
| JPS4948580A (en)) | 1974-05-10 |
| DE2344990C3 (de) | 1981-10-22 |
| FR2200397B1 (en)) | 1978-11-10 |
| FR2200397A1 (en)) | 1974-04-19 |
| DE2344990A1 (de) | 1974-03-21 |
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