US2708185A - Detergent compositions - Google Patents
Detergent compositions Download PDFInfo
- Publication number
- US2708185A US2708185A US114910A US11491049A US2708185A US 2708185 A US2708185 A US 2708185A US 114910 A US114910 A US 114910A US 11491049 A US11491049 A US 11491049A US 2708185 A US2708185 A US 2708185A
- Authority
- US
- United States
- Prior art keywords
- oil
- alkali metal
- sulphates
- removal
- 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.)
- Expired - Lifetime
Links
- 239000003599 detergent Substances 0.000 title claims description 14
- 239000000203 mixture Substances 0.000 title claims description 13
- 239000003921 oil Substances 0.000 claims description 19
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 13
- 239000002480 mineral oil Substances 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 235000010446 mineral oil Nutrition 0.000 claims description 10
- 239000001117 sulphuric acid Substances 0.000 claims description 10
- 235000011149 sulphuric acid Nutrition 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 239000003079 shale oil Substances 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- -1 alkyl sulphates Chemical class 0.000 description 17
- 239000000839 emulsion Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- 229910021653 sulphate ion Inorganic materials 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000000440 bentonite Substances 0.000 description 6
- 229910000278 bentonite Inorganic materials 0.000 description 6
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 6
- 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 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/25—Silicon; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
Definitions
- This invention relates to detergent compositions, suitable for use in the removal of oily materials from surfaces and particularly suitable for the removal of mineral oils or sludges from the hands or other parts of the body.
- a detergent composition consisting of metal alkyl sulphates, of low solubility in water, is obtained by the sulphation of a distillation fraction of shale oil boiling in the approximate range 270 C.360 C. to which is added a filler, such as kieselguhr.
- the composition also comprises a binding agent, for example, a clay, such as bentonite.
- a binding agent for example, a clay, such as bentonite.
- the composition may advantageously have incorporated therein a proportion of refined mineral or fatty oil, for example, a spindle oil. This addition of oil is particularly advantageous where removal of tarry matter is involved, and it aids in producing a smooth paste.
- composition should contain not more than 30% by weight of the filler, 5-2( by weight of the binding agent and not more than by weight of oil.
- the metal alkyl sulphates for use in the detergent composition of the invention are preferably prepared as follows: A shale oil distillate boiling in the approximate range 270 C.-360 C. and preferably derived from Scottish shale, is given a preliminary treatment with dilute sulphuric acid and with aqueous soda solution for the removal of nitrogen bases and phenols, and thereafter contacted with strong sulphuric acid.
- the sulphuric acid used is preferably 96l00% strength and in an amount constituting from 10% to and preferably about 12-13% by volume of the oil feed.
- the sulphuric acid is intimately contacted with the oil while maintaining the temperature of the reactants below 20 C. and preferably at about 5 C.- 20 C.
- reaction mixture containing alkyl hydrogen sulphates and dialkyl sulphates is separated into acid and oil layers in any convenient manner, as by gravity or by centrifuging.
- the alkyl hydrogen sulphates and dialkyl sulphates are converted to metal alkyl sulphates by treatment with a metal hydroxide or carbonate, preferably sodium carbonate. This may be accomplished by adding the acid oil layer, after removal of all traces of acid sludge, to an excess of sodium carbonate in aqueous solution (for example a 16% solution). It is also an advantage to stir the resulting emulsion under a reflux condenser to avoid losses of the more volatile portions of the oils, for an extended period of time, for example 5 hours at 95 C.
- the surface active agents may be recovered from this emulsion by adding an aqueous alcholoic solution with stirring.
- the upper oily layer after extraction has been found to contain alcohols of the order of 15% by weight, which may be recovered by distillation.
- the alcohol free oil may be redistilled after suitable refining treatment, such for example as distillation with steam and lime, or catalytic desulphurisation. Alcohol free unreacted oil may alternatively be blended back with the feed to the process, as it has been found to contain appreciable quantities of sulphatable olefins.
- the proportion of residual oil in the alcoholic detergent solution after emulsion break is about 12% by weight of the sodium alkyl sulphate solution after evaporation of the alcohol.
- the separated alcoholic detergent solution is evaporated to a thin paste or emulsion containing about 12 /2 by weight of sodium alkyl sulphates (calculated as CzoHnSOaONa) and admixed with filler, and if desired a binding agent, mineral oil, and other auxiliary ingredients, customarily employed in the art, such as antiseptic, deodorant and colouring matter.
- sodium alkyl sulphates calculated as CzoHnSOaONa
- Example 1 A sodium alkyl sulphate aqueous paste prepared from a Scottish shale oil distillate fraction boiling in the range 270-360 C., as described above, and containing approximately l2 /z% by weight of sodium alkyl sul-j phates, was admixed with bentonite and kieselguhr in the following proportions by weight:
- Example 2 A sodium alkyl sulphate aqueous paste as in Example 1, and containing 12 /z% by weight of sodium alkyl sulphates, was admixed with bentonite, kieselguhr, refined mineral oil and water in the following proportions by weight:
- metal alkyl sulphates in the form of an aqueous paste containing about 12.5% by weight of the alkali metal alkyl sulphates are admixed with the filler.
Description
United States Patent DETERGENT COMPOSITIONS Daniel Stewart, Broxburn, West Lothian, Scotland, as-
signor to Scottish Oils Limited, Glasgow, Scotland, 21 British joint-stock corporation No Drawing. Application September 9, 1949, Serial N0. 114,910
Claims priori application Great Britain September 15, 1948 22 Claims. (Cl. 252-161) This invention relates to detergent compositions, suitable for use in the removal of oily materials from surfaces and particularly suitable for the removal of mineral oils or sludges from the hands or other parts of the body.
According to the invention, a detergent composition consisting of metal alkyl sulphates, of low solubility in water, is obtained by the sulphation of a distillation fraction of shale oil boiling in the approximate range 270 C.360 C. to which is added a filler, such as kieselguhr.
Preferably the composition also comprises a binding agent, for example, a clay, such as bentonite. We have also found that the composition may advantageously have incorporated therein a proportion of refined mineral or fatty oil, for example, a spindle oil. This addition of oil is particularly advantageous where removal of tarry matter is involved, and it aids in producing a smooth paste.
It is preferred that the composition should contain not more than 30% by weight of the filler, 5-2( by weight of the binding agent and not more than by weight of oil.
The metal alkyl sulphates for use in the detergent composition of the invention are preferably prepared as follows: A shale oil distillate boiling in the approximate range 270 C.-360 C. and preferably derived from Scottish shale, is given a preliminary treatment with dilute sulphuric acid and with aqueous soda solution for the removal of nitrogen bases and phenols, and thereafter contacted with strong sulphuric acid.
The sulphuric acid used is preferably 96l00% strength and in an amount constituting from 10% to and preferably about 12-13% by volume of the oil feed. The sulphuric acid is intimately contacted with the oil while maintaining the temperature of the reactants below 20 C. and preferably at about 5 C.- 20 C.
The reaction mixture containing alkyl hydrogen sulphates and dialkyl sulphates is separated into acid and oil layers in any convenient manner, as by gravity or by centrifuging.
The alkyl hydrogen sulphates and dialkyl sulphates are converted to metal alkyl sulphates by treatment with a metal hydroxide or carbonate, preferably sodium carbonate. This may be accomplished by adding the acid oil layer, after removal of all traces of acid sludge, to an excess of sodium carbonate in aqueous solution (for example a 16% solution). It is also an advantage to stir the resulting emulsion under a reflux condenser to avoid losses of the more volatile portions of the oils, for an extended period of time, for example 5 hours at 95 C. The surface active agents may be recovered from this emulsion by adding an aqueous alcholoic solution with stirring. It has been found that a solution containing lO-% by weight of iso-propyl alcohol in water gives satisfactory results, but that other alcohols, for example, methanol, may be used. The quantity of alcoholic solution added should be sufiicient to give two clear layers 2,708,185 Patented May 10, 1955 in 15 to 30 minutes. The amount of oil retained in the lower layer after breaking the emulsion is considerably influenced by the proportions of alcohol and water relative to detergent, and by the composition of the alcohol. A treatment of the emulsion with an equal volume of aqueous alcoholic solution containing between 15 and 25 parts by weight of isopropyl alcohol suffices to break the emulsion in a reasonable time. The upper oily layer after extraction, has been found to contain alcohols of the order of 15% by weight, which may be recovered by distillation. The alcohol free oil may be redistilled after suitable refining treatment, such for example as distillation with steam and lime, or catalytic desulphurisation. Alcohol free unreacted oil may alternatively be blended back with the feed to the process, as it has been found to contain appreciable quantities of sulphatable olefins.
It has been found that the proportion of residual oil in the alcoholic detergent solution after emulsion break is about 12% by weight of the sodium alkyl sulphate solution after evaporation of the alcohol.
The separated alcoholic detergent solution is evaporated to a thin paste or emulsion containing about 12 /2 by weight of sodium alkyl sulphates (calculated as CzoHnSOaONa) and admixed with filler, and if desired a binding agent, mineral oil, and other auxiliary ingredients, customarily employed in the art, such as antiseptic, deodorant and colouring matter.
The invention is illustrated but in no way limited by the following examples:
Example 1 A sodium alkyl sulphate aqueous paste prepared from a Scottish shale oil distillate fraction boiling in the range 270-360 C., as described above, and containing approximately l2 /z% by weight of sodium alkyl sul-j phates, was admixed with bentonite and kieselguhr in the following proportions by weight:
Per cent Sodium alkyl sulphate paste 68 Bentonite 8 Kieselguhr (7-9 microns average particle size) 24 Example 2 A sodium alkyl sulphate aqueous paste as in Example 1, and containing 12 /z% by weight of sodium alkyl sulphates, was admixed with bentonite, kieselguhr, refined mineral oil and water in the following proportions by weight:
Per cent Sodium alkyl sulphate paste Bentonite l5 Kieselguhr (3-10 microns average particle size) 26 Refined mineral oil 9 Water 10 The resulting paste in each case was a good detergent for the removal of oily contaminants, and was found particularly suitable for cleansing the hands of mineral lubricating oils and sludges. The cleansing action for mineral oil was not reduced by use with hard or salt water. The detergent paste was equally effective if the dirt contained weak acids or metallic salts (such as zinc chloride) which normally render ordinary soapbearing hand cleansers useless. Owing to the fine state of division of the mineral matter, the paste could be used in the cleaning of painted surfaces without the fear of scratching.
I claim:
1. A process for the production of a detergent composition suitable for the removal of oily materials from surfaces and particularly for the removal of mineral oil and sludges from the hands and other parts of the...
body, which comprises sulphating a shale oil distillation fraction boiling within the approximate range 270 C.- 360 C. with strong sulphuric acid-in an amount'con stitutingi 1020% by volume of said distillation ifrac tion, neutralising the product with an alkali metal base to produce alkali metal alkyl sulphates of low solubility in water and admixing the said alkali metal alkyl sulphates with kieselguhr as a filler. V
2. A process according to claim 1 in which the phuric acid is of 96100% concentration.
3. A process according to claim 1 in which the sulphuric acid is employed in an, amount constituting 1213% by volume of the distillation fraction reacted therewith.
4. A process according to claim 1 in which the distillation fraction is reacted with sulphuric acid at a temperature below 20 C.
5. A process according to claim 1 in which the distillation fraction is reacted with sulphuric acid at a tem- 9. A process for the production of a detergent composition suitable for the removal of oily materials from surfaces and particularly for the removal of mineral oil' and sludges from the hands and other parts of the body, which comprises sulphating a shale oil distillation fraction boiling within the approximate range 270 C.360 C. by reacting said fraction with strong sulphuric acid in an amount constituting 10-20% by volume of said distillation fraction while maintaining the temperature of the reactants below 20 C.; separating the reaction mixture into acid and oil layers, the acid layer comprising some oil; converting the alkyl hydrogen sulphates and dialkyl sulphates in the acid-oil layer into alkali metal alkyl sulphates by treating said acid-oil layer with an aqueous solution of an alkali metal base whereby an emulsion is formed; breaking the emulsion formed into .hands and other parts of the body, comprising alkali metal alkyl sulphates of low solubility in water, obtained by the sulphation of a distillation fraction of shale oil boiling in the approximate range 270 C.-360 C. using 1020% of the volume .of said fraction of 96-100% concentration by weight sulphuric acid at a temperature in the range 5-20 C. and neutralizing the product with sodium carbonate, and, in admixture with said sulphate,
, metal alkyl sulphates in the form of an aqueous paste containing about 12.5% by weight of the alkali metal alkyl sulphates are admixed with the filler.
12. A process according to claim 1 in which the kieselguhr filler constitutes not-more than 30% by weight of the alkali metal alkyl sulphates.
13. A process according to claim 1 in which bentonite is added as a binding agent in a proportion constituting 5 to 20% by weight of the alkali metal alkyl sulphate.
14. A process according to claim 1 in which mineral oil is incorporated with said alkali metal alkyl sulphates and filler.
15. A process as defined in'claim 14 in which the mineral oil is employed in a proportion constituting not more than 15 by weight of the alkali metal alkyl sulphates;
16. A process as defined in claim 14 wherein 'the mineral oil is spindle oil.
17."A detergent composition prepared in accordance .Withthe process of claim 1.
References Cited in the file of this patent UNITED STATES PATENTS prepared in accordance prepared in accordance prepared in accordance prepared in accordance prepared in accordance 1,738,967 Sadtler Dec. 10, 1929 1,915,820 Engs et al. June 27, 1933 1,990,490 Home et al Feb. 12, 1935 2,067,326 Leatherman July 12, 1937 2,157,320 Buc May 9, 1939 1 2,392,779 Schowalter Jan. 8,1946. 2,529,538 Henry et al. Nov. 14, 1950 FOREIGN PATENTS 166,727 Great Britain July 26,1921 247,940 Great Britain Aug. 5, 1926 583,028 1946 Great Britain Dec. 5,
Claims (1)
1. A PROCESS FOR THE PRODUCTION OF A DETERGENT COMPOSITION SUITABLE FOR THE REMOVAL OF OIL MATERIAL FROM SURFACES AND PARTICALLY FOR THE REMOVAL OF MINERAL OIL AND SLUDGES FROM THE HANDS AND OTHER PARTS OF THE BODY, WHICH COMPRISES SULPHATING A SHALE OIL DISTILLATION FRACTION BOILING WITHIN THE APPROXIMATE RANGE 270* C., 360* C. WITH STRONG SULPHURIC ACID IN AN AMOUNT CONSTITUTING 10-20% BY VOLUME OF SAID DISTILLATION FRACTION, NEUTRALISING THE PRODUCT WITH AN ALKALI METAL BASE TO PRODUCE ALKALI METAL ALKYL SULPHATES OF LOW SOLUBILITY IN WATER AND ADMIXING THE SAID ALKALI METAL ALYKL SULPHATES WITH KIESELGUHR AS A FILLER.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB283056X | 1948-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2708185A true US2708185A (en) | 1955-05-10 |
Family
ID=10273526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US114910A Expired - Lifetime US2708185A (en) | 1948-09-15 | 1949-09-09 | Detergent compositions |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2708185A (en) |
| CH (1) | CH283056A (en) |
| DE (1) | DE868952C (en) |
| GB (1) | GB646765A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2787596A (en) * | 1952-08-12 | 1957-04-02 | Scottish Oils Ltd | Cleaning composition |
| US2787594A (en) * | 1952-08-12 | 1957-04-02 | Scottish Oils Ltd | Spinning oil composition |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4051056A (en) | 1974-09-09 | 1977-09-27 | The Procter & Gamble Company | Abrasive scouring compositions |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB166727A (en) * | 1920-04-26 | 1921-07-26 | Herbert Schaefer | Improvements in the manufacture of disinfectants from sulphurated shale oils |
| GB247940A (en) * | 1925-02-17 | 1926-08-05 | Peter Iwanowitsch Schestakoff | Improvements in and relating to the manufacture of sulphonic acids and the salts thereof from mineral oils |
| US1738967A (en) * | 1927-12-10 | 1929-12-10 | Samuel S Sadtler | Powdered detergent |
| US1915820A (en) * | 1931-06-29 | 1933-06-27 | Shell Dev | Production of alkyl acid esters of polybasic inorganic acids |
| US1990490A (en) * | 1931-06-29 | 1935-02-12 | Joseph W Horne | Method of producing insecticide and the like |
| US2067326A (en) * | 1933-10-17 | 1937-01-12 | Leatherman Martin | Composition for removing fibrous layers from surfaces |
| US2157320A (en) * | 1939-05-09 | Detekgent composition containing | ||
| US2392779A (en) * | 1944-03-07 | 1946-01-08 | Standard Oil Dev Co | Detergent composition |
| GB583028A (en) * | 1941-06-06 | 1946-12-05 | Novag Ag Zurich | Improvements in or relating to body cleansing agents |
| US2529538A (en) * | 1948-07-13 | 1950-11-14 | Procter & Gamble | Sulfonation of olefins |
-
1948
- 1948-09-15 GB GB24305/48A patent/GB646765A/en not_active Expired
-
1949
- 1949-09-09 US US114910A patent/US2708185A/en not_active Expired - Lifetime
- 1949-09-15 CH CH283056D patent/CH283056A/en unknown
- 1949-09-16 DE DEP54979A patent/DE868952C/en not_active Expired
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2157320A (en) * | 1939-05-09 | Detekgent composition containing | ||
| GB166727A (en) * | 1920-04-26 | 1921-07-26 | Herbert Schaefer | Improvements in the manufacture of disinfectants from sulphurated shale oils |
| GB247940A (en) * | 1925-02-17 | 1926-08-05 | Peter Iwanowitsch Schestakoff | Improvements in and relating to the manufacture of sulphonic acids and the salts thereof from mineral oils |
| US1738967A (en) * | 1927-12-10 | 1929-12-10 | Samuel S Sadtler | Powdered detergent |
| US1915820A (en) * | 1931-06-29 | 1933-06-27 | Shell Dev | Production of alkyl acid esters of polybasic inorganic acids |
| US1990490A (en) * | 1931-06-29 | 1935-02-12 | Joseph W Horne | Method of producing insecticide and the like |
| US2067326A (en) * | 1933-10-17 | 1937-01-12 | Leatherman Martin | Composition for removing fibrous layers from surfaces |
| GB583028A (en) * | 1941-06-06 | 1946-12-05 | Novag Ag Zurich | Improvements in or relating to body cleansing agents |
| US2392779A (en) * | 1944-03-07 | 1946-01-08 | Standard Oil Dev Co | Detergent composition |
| US2529538A (en) * | 1948-07-13 | 1950-11-14 | Procter & Gamble | Sulfonation of olefins |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2787596A (en) * | 1952-08-12 | 1957-04-02 | Scottish Oils Ltd | Cleaning composition |
| US2787594A (en) * | 1952-08-12 | 1957-04-02 | Scottish Oils Ltd | Spinning oil composition |
Also Published As
| Publication number | Publication date |
|---|---|
| CH283056A (en) | 1952-05-31 |
| DE868952C (en) | 1953-03-02 |
| GB646765A (en) | 1950-11-29 |
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