US3852221A - Liquid olefin sulfonate detergent - Google Patents
Liquid olefin sulfonate detergent Download PDFInfo
- Publication number
- US3852221A US3852221A US00173314A US17331471A US3852221A US 3852221 A US3852221 A US 3852221A US 00173314 A US00173314 A US 00173314A US 17331471 A US17331471 A US 17331471A US 3852221 A US3852221 A US 3852221A
- Authority
- US
- United States
- Prior art keywords
- component
- percent
- olefin sulfonate
- fatty acid
- vinylidene
- 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 abstract description 47
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 239000007788 liquid Substances 0.000 title claims abstract description 30
- -1 olefin sulfonate Chemical class 0.000 title abstract description 41
- 239000000203 mixture Substances 0.000 claims abstract description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 35
- 229930195729 fatty acid Natural products 0.000 claims description 35
- 239000000194 fatty acid Substances 0.000 claims description 35
- 150000004665 fatty acids Chemical class 0.000 claims description 35
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 35
- 235000019441 ethanol Nutrition 0.000 claims description 33
- 239000004711 α-olefin Substances 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 229940048842 sodium xylenesulfonate Drugs 0.000 claims description 5
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 2
- ZZXDRXVIRVJQBT-UHFFFAOYSA-M Xylenesulfonate Chemical compound CC1=CC=CC(S([O-])(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-M 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims description 2
- 239000003752 hydrotrope Substances 0.000 claims description 2
- 229940071104 xylenesulfonate Drugs 0.000 claims description 2
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical class C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims 2
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 11
- 150000003871 sulfonates Chemical class 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 5
- 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 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
- 235000019865 palm kernel oil Nutrition 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229940074869 marquis Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000375 suspending agent 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/65—Mixtures of anionic with cationic compounds
- C11D1/655—Mixtures of sulfonated products with alkylolamides of carboxylic acids
-
- 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
- C11D1/143—Sulfonic acid esters
-
- 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
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- 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
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
Definitions
- this invention relates to built light duty olefin sulfonate liquid detergent compositions and to a method for providing homogeneous, clear, low temperature stable, liquid detergents based on alphaolefin sulfonates and vinylidene-olefin sulfonates.
- my invention not only provides a liquid detergent that has improved oily-soil removing characteristics and better foam stability than active compounds known to the art such as the alpha-olefin sulfonates and alkylbenzene sulfonates, but my detergents possess the superior characteristics of being clear, homegeneous liquids that are stable with respect to separations of solids under'conditions of low temperature storage, e.g., 30F. to 40F, and are stable with respect to gelling during formulation and/or storage.
- liquid detergent composition that consists essentially of a clear homogeneous liquid of: g
- the olefin sulfonate component (A) is employed in an amount in the range of about to 24 percent by weight thereof based on said detergent composition.
- Said olefin sulfonate component (A) consists essentially of l) alpha-olefin sulfonate and (2) vinylideneolefin sulfonate which are employed in the form of the alkali metal salts, ammonium salts, or substituted ammonium salts, such as the sodium, potassium, ammonium and ethanolamine salts of the respective sulfonates, and mixtures thereof.
- Said alpha-olefin sulfonate (l) is employed in an amount sufficient to provide in the range of about 7 to 60 wt. percent, preferably 30 to 60 wt. percent, based on the total weight of said olefin sulfonate component (A).
- Said alpha-olefin sulfonate (1) consists essentially of C to C alpha-olefin sulfonates, and mixtures thereof, wherein the C alpha-olefin sulfonate is employed in an amount sufficient to provide in the range of about 50 to 100 wt. percent, based on the total weight of said alpha-olefin sulfonate (1) and the C alpha-olefin sulfonate is employed in an amount to provide in the range of about 0 to 50 wt. percent, preferably 0 to 20 wt. percent, based on the total weight of said alphaolefin sulfonate (l).
- the vinylidene-olefin sulfonate (2) is employed in an amount sufficient to provide in the range of about 40 to 93 wt. percent, preferably about 40 to wt. percent, based on the total weight of said olefin sulfonate component (A).
- the vinylideneolefin sulfonate (2) consists essentially of sulfonates of C to C vinylidene olefin, and mixtures thereof, said vinylidene olefins being represented by the following formula:
- R and R are independently alkyl groups and the total carbon atoms in said groups are in the range from 12 to l4. Further, when the said vinylidene-olefin sulfonate (2) contains 95 percent by weight or more C vinylidene-olefin sulfonate the totalamount of said vinylidene-olefin sulfonate (2) should not exceed about percent by weight of the total weight of said olefin sulfonate component (A).
- said olefin sulfonate component (A) consists essentially of the abovedescribed components, it need not be entirely pure and can contain small amounts, e.g., not more than 10 percent by weight of the total weight of the olefin sulfonate component (A) of sulfonated products of internal olefins, diolefins, olefins containing carbon atoms per molecule greater (such as C C and the like), or less (such as C and the like) than the aforementioned components, mixtures thereof, and the like.
- a small quantity, of the order 1 to 5 percent, of unsulfonated oil may also be present in the olefin sulfonate component (A).
- the alcohol ether sulfate component (B) can be represented by the following formula:
- R" represents a C to C alkyl group
- x is an integer of 2 to 5
- M represents a cation such as an alkali metal, e.g., sodium, potassium, and the like, ammonium, substituted ammonium, such as alkanolamine, e.g., ethanolamine, and the like, or admixtures thereof.
- the above-described component (B) is a sulfated monohydric alcohol polyethoxylate and can be derived from synthetic alcohols, such as lauryl alcohol or natural alcohol, such as those from coconut oil, palm-kernel oil, and the like, or admixtures thereof.
- Said alcohol ether sulfate component (B) can be made conventionally by the condensation of 2 to 5 mols of ethylene oxide on to an aliphatic monohydric alcohol having in the range of about 10 to 18, preferably about 10 to 14, carbon atoms per molecule.
- the ethoxylated alcohol is sulfated and neutralized by known methods.
- the alcohol ether sulfate component (B) comprises about to 13 percent by weight of said detergent composition.
- the substituted fatty acid amide component (C) comprises a fatty acid portion and a substituted amide portion.
- the fatty acid portion is derived from an aliphatic acid containing in the range of 10 to 18 carbon atoms per molecule.
- the fatty acid can be derived from a natural source, such as the fatty acids derived from coconut oil, palm-kernel oil, and the like, and mixtures thereof, or a synthetic acid, such as lauric, myristic, palmitic, linoleic, and the like, and mixtures thereof.
- the substituted acid amide is selected from fatty acid monoethanolamide, fatty acid monoisopropylamide, fatty acid diethanolamide, and fatty acid glycerylamide, and mixtures thereof.
- the substituted fatty acid amide component (C) preferably is employed in an amount to provide in the range of about 4 to 6 percent by weight thereof, based on the total weight of said detergent composition.
- the sulfonated hydrotrope component (D) is selected from the alkali metal salts of xylene sulfonate, toluene sulfonate, benzene sulfonate, or admixtures thereof. Sodium xylene sulfonate is presently preferred.
- said sulfonated hydrotrope component (D) is employed in an amount to provide in the range of about 2 to 6 percent by weight thereof, based on the total weight of said detergent composition.
- the monohydric water-miscible alcohol component (B) preferably is employed in an amount to provide about 2 to 6 percent by weight thereof, based'on the total weight of said detergent composition.
- exemplary alcohols include ethanol, isopropanol, admixtures thereof, and the like.
- said detergent composition can contain the usual ingredients conventionally included in liquid detergents, such as coloring agents, perfumes, bacteriocides, suspending agents, and the like.
- the water component (F) is preferably employed in an amount sufficient to provide about 45 to 61 percent by weight thereof, based on the total weight of said detergent composition. It should be understood that it is not necessary to add water per se as an individual component, but that the water can be supplied by using aqueous solutions of the heretofore mentioned components. For example, olefin sulfonate aqueous slurries, sulfonated hydrotrope aqueous solutions, and the like, are customarily employed.
- components (B) through (F), above-described are conventionally employed in liquid detergent formulations. This is advantageous since these components are already favorably recognized in the industry.
- Our novel compositions therefore, employ heretofore established components in combination with select quantities of particular olefin sulfonates to provide a novel and surprising olefin sulfonate based liquid detergent composition.
- alpha-olefin sulfonates such as above-mentioned
- the conventionally employed components (B) and (C) e.g., the alcohol ether sulfonates and the fatty acid alkanolamides, respectively
- a blob of gel immediately began to form which thickened upon the continued addition of the components.
- a clear homogeneous liquid detergent employing such a combination looked hopeless.
- the detersive performance of the liquid detergent compositions of my invention is appreciably better than the detersiveness of identical detergents based on linear alkylbenzene sulfonates (LAS).
- the liquid detergent compositions of my invention also exhibit even more improved detersive performance with increasing water hardness. At the level of ppm. hardness, for example, the liquid detergent compositions of my invention give about 25 percent better detersive performance than a liquid detergent employing LAS.
- the components can be admixed in any order that is convenient to the practitioner. It is presently preferred, however, to admix the olefin sulfonate component (A) with the alcohol component (E) and the sulfonated hydrotrope component (D) and at least a portion of the water (F) prior to admixing the alcohol ether sulfate component (B) and the substituted fatty acid amide component (C). Regardless of the order of mixing, however, the olefin sulfonate component (A) of this invention will surprisingly dissolve readily with the other components of the formulation to provide a clear homogeneous liquid detergent composition.
- a detergent composition consisting essentially of a clear homogeneous liquid of (A) 19 to 30 wt. percent of anolefin sulfonate component; (B) 8 to 15 wt. percent of an alcohol ether sulfate component; (C) 3 to 7 wt. percent of a substituted fatty acid amide component; (D) l to 8 wt. percent of a sulfonated hydrotrope component; (E) l to 8 wt. percent of a monohydric water-miscible alcohol; and (F) 32 to 68 wt. percent water; wherein said component (A) consists essentially of (l 7 to wt.
- composition of claim 1 wherein said component (A) consists essentially of 30 to 60 wt. percent of said alpha-olefin sulfonate and 70 to 40 wt. percent of said vinylidene-olefin sulfonate.
- composition of claim 3 wherein said vinylidene-olefin sulfonate consists essentially of C vinylidene-olefin sulfonate.
- composition of claim 3 wherein said component (B) is a sulfated 2 to mol ethoxylate of a C to C monohydric alcohol, said component (C) is a fatty acid ethanolamide or fatty acid diethanolamide, wherein said component (D) is sodium xylene sulfonate, and wherein said component (E) is ethyl alcohol.
- composition of claim 2 wherein said component (B) is a sulfated 2 to 5 mol ethoxylate of a C to C monohydric alcohol, said component (C) is a fatty acid ethanolamide or fatty acid diethanolamide, wherein said component (D) is sodium xylene .sulfonate, and wherein said component (B) is ethyl alcohol.
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- Chemical & Material Sciences (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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00173314A US3852221A (en) | 1971-08-19 | 1971-08-19 | Liquid olefin sulfonate detergent |
| CA148,013A CA976448A (en) | 1971-08-19 | 1972-07-26 | Liquid olefin sulfonate detergent |
| GB3785672A GB1341937A (en) | 1971-08-19 | 1972-08-14 | Liquid detergent compositions containing olefin sulphonates |
| JP47083265A JPS501127B2 (enrdf_load_stackoverflow) | 1971-08-19 | 1972-08-19 | |
| DE2241031A DE2241031A1 (de) | 1971-08-19 | 1972-08-21 | Waschmittel und verfahren zu seiner herstellung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00173314A US3852221A (en) | 1971-08-19 | 1971-08-19 | Liquid olefin sulfonate detergent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3852221A true US3852221A (en) | 1974-12-03 |
Family
ID=22631458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00173314A Expired - Lifetime US3852221A (en) | 1971-08-19 | 1971-08-19 | Liquid olefin sulfonate detergent |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3852221A (enrdf_load_stackoverflow) |
| JP (1) | JPS501127B2 (enrdf_load_stackoverflow) |
| CA (1) | CA976448A (enrdf_load_stackoverflow) |
| DE (1) | DE2241031A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1341937A (enrdf_load_stackoverflow) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3954676A (en) * | 1973-09-26 | 1976-05-04 | Ethyl Corporation | Sulfonate detergents |
| US3954679A (en) * | 1973-11-26 | 1976-05-04 | Colgate-Palmolive Company | Viscosity reduction of aqueous alpha-olefin sulfonate detergent composition |
| US3979340A (en) * | 1973-04-09 | 1976-09-07 | Colgate-Palmolive Company | Olefin sulfonate detergent compositions |
| US3985687A (en) * | 1974-12-26 | 1976-10-12 | Colgate-Palmolive Company | Liquid detergent compositions of controlled viscosities |
| US4003857A (en) * | 1973-12-17 | 1977-01-18 | Ethyl Corporation | Concentrated aqueous olefins sulfonates containing carboxylic acid salt anti-gelling agents |
| US4259216A (en) * | 1979-10-11 | 1981-03-31 | The Lion Fat & Oil Co., Ltd. | Process for producing liquid detergent composition |
| US4367169A (en) * | 1980-10-27 | 1983-01-04 | Lion Corporation | α-Olefin sulfonate-containing, liquid detergent compositions having improved low-temperature stability |
| US4507223A (en) * | 1982-08-10 | 1985-03-26 | Lion Corporation | High concentration surfactant slurry |
| US4715991A (en) * | 1985-04-26 | 1987-12-29 | Lion Corporation | Aqueous high concentration surfactant slurry containing an olefin sulfonate |
| WO2001027228A1 (en) * | 1999-10-12 | 2001-04-19 | Colgate-Palmolive Company | Homogenous solution of an alpha olefin sulfonate surfactant |
| CN103429696A (zh) * | 2010-12-29 | 2013-12-04 | 国际壳牌研究有限公司 | 从含有原油的地层中强化烃采收的方法和组合物 |
| WO2014193731A1 (en) | 2013-05-31 | 2014-12-04 | Dow Global Technologies Llc | A low temperature stabilized foam-forming composition for enhanced oil recovery |
| US20160002571A1 (en) * | 2013-03-13 | 2016-01-07 | Stepan Company | Surfactants based on monounsaturated fatty alcohol derivatives |
| US10006515B2 (en) * | 2013-09-26 | 2018-06-26 | Kyoraku Co., Ltd. | Impact energy absorber |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5657212U (enrdf_load_stackoverflow) * | 1979-10-04 | 1981-05-18 | ||
| GB2123847A (en) * | 1982-06-28 | 1984-02-08 | Procter & Gamble | Liquid detergent compositions |
| JPS60169218U (ja) * | 1984-04-13 | 1985-11-09 | 公徳商事株式会社 | エプロン |
| TR22593A (tr) * | 1987-05-18 | 1987-12-15 | Ahmet Ecevit | Kendinden depolu uecgen prizma tipli duez guenes toplayici |
| US5223179A (en) * | 1992-03-26 | 1993-06-29 | The Procter & Gamble Company | Cleaning compositions with glycerol amides |
| DE4311158A1 (de) * | 1993-04-05 | 1994-10-06 | Henkel Kgaa | Flüssiges Reinigungsmittel |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3332876A (en) * | 1964-10-15 | 1967-07-25 | Procter & Gamble | Detergent composition |
| US3332877A (en) * | 1965-01-04 | 1967-07-25 | Procter & Gamble | Detergent composition |
| US3332879A (en) * | 1966-12-05 | 1967-07-25 | Procter & Gamble | Ternary synergistic sudsing detergent compositions |
| US3415753A (en) * | 1964-06-26 | 1968-12-10 | Henkel & Cie Gmbh | Liquid and paste detergent concentrates |
| GB1139158A (en) * | 1966-05-11 | 1969-01-08 | Henkel & Cie Gmbh | Process for the preparation of olefine sulphonates |
| US3428654A (en) * | 1965-08-04 | 1969-02-18 | Colgate Palmolive Co | Alkene sulfonation process and products |
| US3492239A (en) * | 1966-07-01 | 1970-01-27 | Henkel & Cie Gmbh | Light-colored sulfonation products |
| US3544475A (en) * | 1967-09-29 | 1970-12-01 | Lion Fat Oil Co Ltd | Detergent compositions based on mixtures of alpha-olefin sulfonates and dimer olefin sulfonates |
| DE1961963A1 (de) * | 1968-12-11 | 1970-12-10 | Lion Fat Oil Co Ltd | Verfahren zur Sulfonierung eines Olefingemisches |
| US3640880A (en) * | 1967-12-06 | 1972-02-08 | Lever Brothers Ltd | Hard surface cleaner |
| US3691108A (en) * | 1969-08-29 | 1972-09-12 | Sumitomo Chemical Co | Olefin sulfonate detergent composition |
-
1971
- 1971-08-19 US US00173314A patent/US3852221A/en not_active Expired - Lifetime
-
1972
- 1972-07-26 CA CA148,013A patent/CA976448A/en not_active Expired
- 1972-08-14 GB GB3785672A patent/GB1341937A/en not_active Expired
- 1972-08-19 JP JP47083265A patent/JPS501127B2/ja not_active Expired
- 1972-08-21 DE DE2241031A patent/DE2241031A1/de active Pending
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3415753A (en) * | 1964-06-26 | 1968-12-10 | Henkel & Cie Gmbh | Liquid and paste detergent concentrates |
| US3332876A (en) * | 1964-10-15 | 1967-07-25 | Procter & Gamble | Detergent composition |
| US3332877A (en) * | 1965-01-04 | 1967-07-25 | Procter & Gamble | Detergent composition |
| US3428654A (en) * | 1965-08-04 | 1969-02-18 | Colgate Palmolive Co | Alkene sulfonation process and products |
| GB1139158A (en) * | 1966-05-11 | 1969-01-08 | Henkel & Cie Gmbh | Process for the preparation of olefine sulphonates |
| US3492239A (en) * | 1966-07-01 | 1970-01-27 | Henkel & Cie Gmbh | Light-colored sulfonation products |
| US3332879A (en) * | 1966-12-05 | 1967-07-25 | Procter & Gamble | Ternary synergistic sudsing detergent compositions |
| US3544475A (en) * | 1967-09-29 | 1970-12-01 | Lion Fat Oil Co Ltd | Detergent compositions based on mixtures of alpha-olefin sulfonates and dimer olefin sulfonates |
| US3640880A (en) * | 1967-12-06 | 1972-02-08 | Lever Brothers Ltd | Hard surface cleaner |
| DE1961963A1 (de) * | 1968-12-11 | 1970-12-10 | Lion Fat Oil Co Ltd | Verfahren zur Sulfonierung eines Olefingemisches |
| US3691108A (en) * | 1969-08-29 | 1972-09-12 | Sumitomo Chemical Co | Olefin sulfonate detergent composition |
Non-Patent Citations (1)
| Title |
|---|
| Marquis et al., Alpha Olefin Sulfonates from a Commercial SO Air Reactor, JOACS, SEPT. 1966, pp. 607 614. * |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3979340A (en) * | 1973-04-09 | 1976-09-07 | Colgate-Palmolive Company | Olefin sulfonate detergent compositions |
| US3954676A (en) * | 1973-09-26 | 1976-05-04 | Ethyl Corporation | Sulfonate detergents |
| US3954679A (en) * | 1973-11-26 | 1976-05-04 | Colgate-Palmolive Company | Viscosity reduction of aqueous alpha-olefin sulfonate detergent composition |
| US4003857A (en) * | 1973-12-17 | 1977-01-18 | Ethyl Corporation | Concentrated aqueous olefins sulfonates containing carboxylic acid salt anti-gelling agents |
| US3985687A (en) * | 1974-12-26 | 1976-10-12 | Colgate-Palmolive Company | Liquid detergent compositions of controlled viscosities |
| US4259216A (en) * | 1979-10-11 | 1981-03-31 | The Lion Fat & Oil Co., Ltd. | Process for producing liquid detergent composition |
| US4367169A (en) * | 1980-10-27 | 1983-01-04 | Lion Corporation | α-Olefin sulfonate-containing, liquid detergent compositions having improved low-temperature stability |
| US4507223A (en) * | 1982-08-10 | 1985-03-26 | Lion Corporation | High concentration surfactant slurry |
| US4715991A (en) * | 1985-04-26 | 1987-12-29 | Lion Corporation | Aqueous high concentration surfactant slurry containing an olefin sulfonate |
| WO2001027228A1 (en) * | 1999-10-12 | 2001-04-19 | Colgate-Palmolive Company | Homogenous solution of an alpha olefin sulfonate surfactant |
| CN103429696A (zh) * | 2010-12-29 | 2013-12-04 | 国际壳牌研究有限公司 | 从含有原油的地层中强化烃采收的方法和组合物 |
| EP2658946A4 (en) * | 2010-12-29 | 2014-05-14 | Shell Oil Co | METHOD AND COMPOSITION FOR REINFORCED CARBON HYDROGEN RECYCLING FROM A CRUDE-OIL FORMATION |
| US20160002571A1 (en) * | 2013-03-13 | 2016-01-07 | Stepan Company | Surfactants based on monounsaturated fatty alcohol derivatives |
| US9695385B2 (en) * | 2013-03-13 | 2017-07-04 | Stepan Company | Surfactants based on monounsaturated fatty alcohol derivatives |
| US10287530B2 (en) | 2013-03-13 | 2019-05-14 | Stepan Company | Surfactants based on monounsaturated fatty alcohol derivatives |
| US11560530B2 (en) | 2013-03-13 | 2023-01-24 | Stepan Company | Surfactants based on monounsaturated fatty alcohol derivatives |
| WO2014193731A1 (en) | 2013-05-31 | 2014-12-04 | Dow Global Technologies Llc | A low temperature stabilized foam-forming composition for enhanced oil recovery |
| US10006515B2 (en) * | 2013-09-26 | 2018-06-26 | Kyoraku Co., Ltd. | Impact energy absorber |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1341937A (en) | 1973-12-25 |
| CA976448A (en) | 1975-10-21 |
| DE2241031A1 (de) | 1973-03-08 |
| JPS4830712A (enrdf_load_stackoverflow) | 1973-04-23 |
| JPS501127B2 (enrdf_load_stackoverflow) | 1975-01-16 |
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