US3686127A - Detergent bleach - Google Patents
Detergent bleach Download PDFInfo
- Publication number
- US3686127A US3686127A US105954A US3686127DA US3686127A US 3686127 A US3686127 A US 3686127A US 105954 A US105954 A US 105954A US 3686127D A US3686127D A US 3686127DA US 3686127 A US3686127 A US 3686127A
- Authority
- US
- United States
- Prior art keywords
- detergent
- compounds
- bleaching
- alkyl
- alkali metal
- 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
- 239000003599 detergent Substances 0.000 title abstract description 42
- 239000007844 bleaching agent Substances 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 41
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 13
- 150000001340 alkali metals Chemical group 0.000 abstract description 12
- 239000002243 precursor Substances 0.000 abstract description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract description 3
- 150000003863 ammonium salts Chemical class 0.000 abstract description 3
- 238000010348 incorporation Methods 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 36
- 238000004061 bleaching Methods 0.000 description 27
- -1 alkylbenzene sulphonate Chemical class 0.000 description 14
- 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 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 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 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 150000004965 peroxy acids Chemical class 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229960001922 sodium perborate Drugs 0.000 description 5
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000001226 triphosphate Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000011180 diphosphates Nutrition 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 235000011178 triphosphate Nutrition 0.000 description 2
- OWTIQEOUATWBMC-UHFFFAOYSA-N (2-dodecylphenyl) acetate Chemical compound C(C)(=O)OC1=C(C=CC=C1)CCCCCCCCCCCC OWTIQEOUATWBMC-UHFFFAOYSA-N 0.000 description 1
- JVBQARGGMQCWSH-UHFFFAOYSA-N 2-acetyloxy-5-nonylbenzenesulfonic acid Chemical compound CCCCCCCCCC1=CC=C(OC(C)=O)C(S(O)(=O)=O)=C1 JVBQARGGMQCWSH-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 238000005618 Fries rearrangement reaction Methods 0.000 description 1
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
- CVXHBROPWMVEQO-UHFFFAOYSA-N Peroxyoctanoic acid Chemical compound CCCCCCCC(=O)OO CVXHBROPWMVEQO-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SHDMEQUHXHMDNM-UHFFFAOYSA-N benzenesulfonyl hexanoate Chemical compound CCCCCC(=O)OS(=O)(=O)C1=CC=CC=C1 SHDMEQUHXHMDNM-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000011368 organic material Substances 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
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- 229940045872 sodium percarbonate Drugs 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 239000013042 solid detergent Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 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
- C11D3/3915—Sulfur-containing compounds
Definitions
- the compounds are therefore suited for incorporation in washing products.
- This invention relates to detergent and bleaching-aid compounds, and to detergent bleaching compositions, in particular to compositions suitable for washing textile materials and removing stains therefrom at relatively low temperatures.
- detergent compositions contain an inorganic persalt, such as sodium perborate or percarbonate to provide bleaching properties.
- persalts provide a satisfactory bleach when the composition is used at or near the boil, but at lower temperatures, e.g., 50-60 C., their action is rather slow, even too slow to be really efiective within the normal bleaching time. This is particularly disadvantageous when using washing machines which operate at this temperature range.
- the invention further provides a detergent bleaching composition containing a perhydrate or an inorganic persalt and the above-defined organic compound.
- persalt is meant a compound, more precisely termed peroxyhydrate, containing hydrogen peroxide of crystallization which is liberated when the substance is dissolved in water.
- Suitable compountk are alkali metal perborates, percarbonates, perpyrophosphates and persilicates, and also urea peroxide.
- the compounds according to the invention not only enhance the bleaching action of persalts at low temperatures, but also possess detergent and emulsifying properties comparable to alkylbenzene sulphonate and hence they are detergent actives having simultaneously peracid precursor activity.
- the compound according to our invention forms percarboxylic acid and the respective phenol sulphonate at relatively low temperature, of which products the former as distinct from sodium perborate or H O, has eflicient bleaching activity at low temperature and the latter has detergent properties, e.g.,
- washing etliciency increases with increasing chain length of the alkyl or acyl group X.
- Suitable compounds giving satisfactory performance are those in'which the alkyl or acyl group X contains 6-17 carbon atoms. Compounds in which X C H or C H CO are almost or completely insoluble in water; compounds in which X C H or C H CO have poor washingefiiciency.
- the preferred compounds are those in which 'X is a branched or straight chain alkyl or acyl radical containing 8-14 carbon atoms.
- percarboxylic acids in general are efiicient bleaching agents at lower temperatures
- R is H or an alkyl radical having 1-7 carbon atoms.
- the preferred compounds are those in which R is methyl, i.e., acetoxy alkylbenzene sulphonates or acetoxy acylbenzene sulphonates, since they are easy to prepare.
- alkylphenol may be a commercially avilable alkylphenol, e.g., nonylphenol, octylphenol, etc. or may be prepared from phenol through acylation and Fries rearrangement to acylphenol followed by reduction. Acetoxy-acylbenzene sulphonates may be obtained by leaving out the reduction step.
- an inorganic persalt such as sodium perborate
- the invention may also be applied to bleaching baths such as are used for treating textiles, to wash liquors, such as are usedin commercial or domestic laundering.
- Solid detergent hje'ac I compositions may contain, in addition to a persaltand "the compound according to the invention, inert sii ts g d alkaline agents.
- An additional amount of organic detergent which may be soap and/or an organic anionic and/or nonionic type soapless detergent, may also be incorporated, but is not necessary.
- compositions which contain mere esters as the bleach enhancer are both valuable substances, as distinct from those obtained from the perhydrolysis of known esters of which the alcoholic part is more or less an inactive byproduct.
- Detergent bleaching compositions according to the invention should preferably contain one or more alkaline substances in such amounts that similar compositions not containing esters would give a pH value within the range 9-11 when dissolved at the desired bleaching concentration.
- Suitable alkaline materials are, for instance, alkali metal carbonates, phosphates (including orthophosphates and water-soluble condensed phosphates, such as triphosphates and pyrophosphates) and silicates.
- compositions according to the invention may also contain any of the conventional adjuncts present in detergent compositions.
- supplementary builders inert salts and organic materials such as alkali metal sulphates, chlorides, carboxymethylcellulose, fluorescent agents and germicidal compounds.
- the compositions must not contain water in a state and in an amount sufficient to permit appreciable chemical reaction between the components prior to use.
- the proportion of the persalt to the new organic compound which may be present in compositions according to the invention will depend on the time and temperature of washing and bleaching, the degree of bleaching required and the concentration of the wash and bleaching solution.
- the determination is based on iodometric titration of the amount of peracetic acid which is formed in an aqueous solution at 20' C. from the precursor and hydrogen peroxide (as sodium perborate).
- the titration is carried out at C. after Larious periods of time. At this low temperature only the peracid present is titrated, and not the hydrogen peroxide of which an excess is present.
- the perhydrolysis is carried out in alkaline medium the peracid formed decomposes during its formation. Therefore, a
- the maximum peracetic acid yield was 39%, which was reached after 10 minutes.
- the compound was found to have a good solubility at 20 C.
- EXAMPLE 7 The activity of sodium Z-acetoxy-S-lauroylbenzene sulphonate was also determined and the maximum peracetic acid yield found was 65% after 10 minutes.
- the compound was found to have a good solubility at 20 C.
- Test swatches stained with immedial black were washed three times with a solution containing 5.75 g./l. of the above composition during 10 minutes at a temperature of 60 C. with a heating-up time of 20 minutes. As compared with the results obtained with the above composition without sodium Z-acetoxy-S-nonylbenzene sulphonate there was an increase of 5 in whiteness degree.
- the sodium 2-acetoxy-5-nonylbenzene sulphonate was prepared as follows:
- a detergent bleaching composition which contains 1) an inorganic persalt selected from the group consisting of alkali metal perborates, alkali metal percarbonates, alkali metal perpyrophosphates and alkali metal persilicates, and (2) a conjoint organic detergent and bleach precursor compound of the general formula in which X is a branched or straight chain alkyl or alkanoyl radical containing 6-17 carbon atoms, R is a hydrogen or alkyl radical having 1-7 carbon atoms, and M is an alkali metal or ammonium radical; said inorganic persalt being present in at least an equimolar ratio to the said conjoint organic detergent and bleach precursor compound, and said composition being substantially free of water.
- an inorganic persalt selected from the group consisting of alkali metal perborates, alkali metal percarbonates, alkali metal perpyrophosphates and alkali metal persilicates, and (2) a conjoint organic detergent and bleach precursor compound of the general formula in which X is a branche
- the detergent bleaching composition defined by claim 1 which further contains (3) an alkaline material selected from the group consisting of alkali metal car bonates, alkali metal orthophosphates, alkali metal triphosphates, alkali metal pyrophosphates and alkali metal silicates.
- the detergent bleaching composition defined by claim 1 wherein in the general formula of the conjoint organic detergent and bleach precursor compound the R radical is methyl and the X radical in the benzene nucleus is in the para position to the OCOR group.
- the detergent bleaching composition defined by claim 2 which further contains (4) an organic detergent selected from the group consisting of organic nonionie nonsoap detergents, organic anionic nonsoap detergents and soap.
- the detergent bleaching composition defined by claim 8 wherein the conjoint organic detergent and bleach precursor compound is an alkali metal or ammonium salt of 2-acetoxy-5-nonylbenzene sulphonic acid.
- the detergent bleaching composition defined by claim 9 wherein the conjoint organic detergent and bleach precursor compound is sodium 2-acetoxy-5-nonylbenzene sulphonate.
Landscapes
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4027/66A GB1147871A (en) | 1966-01-28 | 1966-01-28 | Acyloxy alkyl or acyl benzene sulphonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3686127A true US3686127A (en) | 1972-08-22 |
Family
ID=9769354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US105954A Expired - Lifetime US3686127A (en) | 1966-01-28 | 1971-01-12 | Detergent bleach |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3686127A (en, 2012) |
| AT (1) | AT277142B (en, 2012) |
| BE (1) | BE693310A (en, 2012) |
| CH (1) | CH500278A (en, 2012) |
| DE (1) | DE1618012A1 (en, 2012) |
| ES (1) | ES336168A1 (en, 2012) |
| GB (1) | GB1147871A (en, 2012) |
| GR (1) | GR33179B (en, 2012) |
| LU (1) | LU52895A1 (en, 2012) |
| NL (1) | NL6701219A (en, 2012) |
| SE (1) | SE323762B (en, 2012) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4430236A (en) | 1981-06-22 | 1984-02-07 | Texize, Division Of Mortonthiokol | Liquid detergent composition containing bleach |
| US4483778A (en) * | 1983-12-22 | 1984-11-20 | The Procter & Gamble Company | Peroxygen bleach activators and bleaching compositions |
| US4486327A (en) * | 1983-12-22 | 1984-12-04 | The Procter & Gamble Company | Bodies containing stabilized bleach activators |
| US4539130A (en) * | 1983-12-22 | 1985-09-03 | The Procter & Gamble Company | Peroxygen bleach activators and bleaching compositions |
| US4606838A (en) * | 1985-03-14 | 1986-08-19 | The Procter & Gamble Company | Bleaching compositions comprising alkoxy substituted aromatic peroxyacids |
| US4681695A (en) * | 1984-09-01 | 1987-07-21 | The Procter & Gamble Company | Bleach compositions |
| US4686061A (en) * | 1985-07-03 | 1987-08-11 | Akzo Nv | P-sulphophenyl carbonates and detergent compositions and detergent additives containing these compounds |
| US4695412A (en) * | 1984-05-26 | 1987-09-22 | Basf Aktiengesellschaft | Preparation of acyloxybenzenesulfonic acids and their alkali metal and alkaline earth metal salts |
| US4751015A (en) * | 1987-03-17 | 1988-06-14 | Lever Brothers Company | Quaternary ammonium or phosphonium substituted peroxy carbonic acid precursors and their use in detergent bleach compositions |
| US4778618A (en) * | 1986-11-06 | 1988-10-18 | The Clorox Company | Glycolate ester peracid precursors |
| US4818426A (en) * | 1987-03-17 | 1989-04-04 | Lever Brothers Company | Quaternary ammonium or phosphonium substituted peroxy carbonic acid precursors and their use in detergent bleach compositions |
| EP0333248A3 (en) * | 1988-03-17 | 1990-08-29 | Unilever N.V. | Bleach precursors and their use in bleaching and/or detergent composition |
| US5055217A (en) * | 1990-11-20 | 1991-10-08 | Lever Brothers Company, Division Of Conopco, Inc. | Polymer protected bleach precursors |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5112514A (en) * | 1986-11-06 | 1992-05-12 | The Clorox Company | Oxidant detergent containing stable bleach activator granules |
| US5002691A (en) * | 1986-11-06 | 1991-03-26 | The Clorox Company | Oxidant detergent containing stable bleach activator granules |
| US5269962A (en) | 1988-10-14 | 1993-12-14 | The Clorox Company | Oxidant composition containing stable bleach activator granules |
| GB9323634D0 (en) * | 1993-11-16 | 1994-01-05 | Warwick Int Ltd | Bleach activator compositions |
| US5399746A (en) * | 1994-02-07 | 1995-03-21 | Witco Corporation | Diquaternary bleach activators and compositions containing them |
| GB2294268A (en) | 1994-07-07 | 1996-04-24 | Procter & Gamble | Bleaching composition for dishwasher use |
| EP0693549A1 (en) | 1994-07-19 | 1996-01-24 | The Procter & Gamble Company | Solid bleach activator compositions |
| GB2320254A (en) | 1996-12-12 | 1998-06-17 | Procter & Gamble | Process for making tabletted detergent compositions |
| AU2003231107A1 (en) | 2002-05-02 | 2003-11-17 | The Procter And Gamble Company | Detergent compositions and components thereof |
| GB0918914D0 (en) | 2009-10-28 | 2009-12-16 | Revolymer Ltd | Composite |
| GB201106409D0 (en) | 2011-04-15 | 2011-06-01 | Revolymer Ltd | Novel composite |
| US20140338134A1 (en) | 2013-05-20 | 2014-11-20 | The Procter & Gamble Company | Encapsulates |
| EP2806018A1 (en) | 2013-05-20 | 2014-11-26 | The Procter & Gamble Company | Encapsulates |
-
1966
- 1966-01-28 GB GB4027/66A patent/GB1147871A/en not_active Expired
-
1967
- 1967-01-26 NL NL6701219A patent/NL6701219A/xx unknown
- 1967-01-27 SE SE1232/67A patent/SE323762B/xx unknown
- 1967-01-27 LU LU52895D patent/LU52895A1/xx unknown
- 1967-01-27 DE DE19671618012 patent/DE1618012A1/de active Pending
- 1967-01-27 AT AT78767A patent/AT277142B/de not_active IP Right Cessation
- 1967-01-27 CH CH122867A patent/CH500278A/de not_active IP Right Cessation
- 1967-01-27 ES ES336168A patent/ES336168A1/es not_active Expired
- 1967-01-27 BE BE693310D patent/BE693310A/xx unknown
- 1967-01-27 GR GR670133179A patent/GR33179B/el unknown
-
1971
- 1971-01-12 US US105954A patent/US3686127A/en not_active Expired - Lifetime
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4430236A (en) | 1981-06-22 | 1984-02-07 | Texize, Division Of Mortonthiokol | Liquid detergent composition containing bleach |
| US4483778A (en) * | 1983-12-22 | 1984-11-20 | The Procter & Gamble Company | Peroxygen bleach activators and bleaching compositions |
| US4486327A (en) * | 1983-12-22 | 1984-12-04 | The Procter & Gamble Company | Bodies containing stabilized bleach activators |
| US4539130A (en) * | 1983-12-22 | 1985-09-03 | The Procter & Gamble Company | Peroxygen bleach activators and bleaching compositions |
| US4695412A (en) * | 1984-05-26 | 1987-09-22 | Basf Aktiengesellschaft | Preparation of acyloxybenzenesulfonic acids and their alkali metal and alkaline earth metal salts |
| US4681695A (en) * | 1984-09-01 | 1987-07-21 | The Procter & Gamble Company | Bleach compositions |
| US4606838A (en) * | 1985-03-14 | 1986-08-19 | The Procter & Gamble Company | Bleaching compositions comprising alkoxy substituted aromatic peroxyacids |
| US4686061A (en) * | 1985-07-03 | 1987-08-11 | Akzo Nv | P-sulphophenyl carbonates and detergent compositions and detergent additives containing these compounds |
| US4778618A (en) * | 1986-11-06 | 1988-10-18 | The Clorox Company | Glycolate ester peracid precursors |
| US4751015A (en) * | 1987-03-17 | 1988-06-14 | Lever Brothers Company | Quaternary ammonium or phosphonium substituted peroxy carbonic acid precursors and their use in detergent bleach compositions |
| US4818426A (en) * | 1987-03-17 | 1989-04-04 | Lever Brothers Company | Quaternary ammonium or phosphonium substituted peroxy carbonic acid precursors and their use in detergent bleach compositions |
| EP0333248A3 (en) * | 1988-03-17 | 1990-08-29 | Unilever N.V. | Bleach precursors and their use in bleaching and/or detergent composition |
| US5055217A (en) * | 1990-11-20 | 1991-10-08 | Lever Brothers Company, Division Of Conopco, Inc. | Polymer protected bleach precursors |
Also Published As
| Publication number | Publication date |
|---|---|
| BE693310A (en, 2012) | 1967-07-27 |
| LU52895A1 (en, 2012) | 1968-08-28 |
| GR33179B (el) | 1967-11-15 |
| GB1147871A (en) | 1969-04-10 |
| SE323762B (en, 2012) | 1970-05-11 |
| DE1618012A1 (de) | 1970-11-05 |
| AT277142B (de) | 1969-12-10 |
| NL6701219A (en, 2012) | 1967-07-31 |
| ES336168A1 (es) | 1968-06-01 |
| CH500278A (de) | 1970-12-15 |
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