US3211661A - Liquid detergent composition - Google Patents
Liquid detergent composition Download PDFInfo
- Publication number
- US3211661A US3211661A US159770A US15977061A US3211661A US 3211661 A US3211661 A US 3211661A US 159770 A US159770 A US 159770A US 15977061 A US15977061 A US 15977061A US 3211661 A US3211661 A US 3211661A
- Authority
- US
- United States
- Prior art keywords
- alkyl
- detergent
- sodium
- composition
- primary
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 72
- 239000003599 detergent Substances 0.000 title claims abstract description 42
- 239000007788 liquid Substances 0.000 title claims abstract description 17
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 18
- 125000000217 alkyl group Chemical group 0.000 abstract description 15
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 abstract description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 11
- 239000011591 potassium Chemical group 0.000 abstract description 11
- 229910052700 potassium Inorganic materials 0.000 abstract description 11
- 229910052708 sodium Inorganic materials 0.000 abstract description 11
- 239000011734 sodium Substances 0.000 abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract description 8
- 239000007795 chemical reaction product Substances 0.000 abstract description 8
- 239000003605 opacifier Substances 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 150000003863 ammonium salts Chemical class 0.000 abstract description 4
- 239000002304 perfume Substances 0.000 abstract description 4
- 238000010992 reflux Methods 0.000 abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 3
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001412 amines Chemical class 0.000 abstract description 3
- 229940096386 coconut alcohol Drugs 0.000 abstract description 3
- 239000002244 precipitate Substances 0.000 abstract description 3
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004793 Polystyrene Substances 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract description 2
- 229920002223 polystyrene Polymers 0.000 abstract description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical group OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 abstract description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 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 abstract 1
- KHIHBOPGYSBYJJ-UHFFFAOYSA-N azane;toluene Chemical compound N.CC1=CC=CC=C1 KHIHBOPGYSBYJJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000008053 sultones Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- -1 triethanolammonium cations Chemical class 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 125000005192 alkyl ethylene group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000002688 persistence Effects 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229940047662 ammonium xylenesulfonate Drugs 0.000 description 2
- IHRIVUSMZMVANI-UHFFFAOYSA-N azane;2-methylbenzenesulfonic acid Chemical compound [NH4+].CC1=CC=CC=C1S([O-])(=O)=O IHRIVUSMZMVANI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HESSGHHCXGBPAJ-UHFFFAOYSA-N n-[3,5,6-trihydroxy-1-oxo-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-yl]acetamide Chemical compound CC(=O)NC(C=O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O HESSGHHCXGBPAJ-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000003166 Opuntia robusta Nutrition 0.000 description 1
- 244000218514 Opuntia robusta Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- IMKUHVCLLRFQBS-UHFFFAOYSA-N azane;phenylmethanesulfonic acid Chemical class [NH4+].[O-]S(=O)(=O)CC1=CC=CC=C1 IMKUHVCLLRFQBS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- GHKGUEZUGFJUEJ-UHFFFAOYSA-M potassium;4-methylbenzenesulfonate Chemical compound [K+].CC1=CC=C(S([O-])(=O)=O)C=C1 GHKGUEZUGFJUEJ-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229940048842 sodium xylenesulfonate Drugs 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- FODHIQQNHOPUKH-UHFFFAOYSA-N tetrapropylene-benzenesulfonic acid Chemical compound CC1CC11C2=C3S(=O)(=O)OC(C)CC3=C3C(C)CC3=C2C1C FODHIQQNHOPUKH-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/92—Sulfobetaines ; Sulfitobetaines
-
- 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
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/94—Mixtures with anionic, cationic or non-ionic 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
- C11D3/43—Solvents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
- Y10S516/05—Organic amine, amide, or n-base containing
Definitions
- the quantity and persistence of suds are very important in a light duty liquid detergent which will 'be used for dishwashing and the like.
- the user is accustomed to gauging the detergency capacity of a washing solution by the amount of suds present and will very likely be misled if the suds do not persist for a reasonable period of time.
- An ideal liquid detergent composition is clear and colorless, permitting the formulation of a wide variety of opaque, clear, colorless, and colored detergents.
- the most common suds builders for such products are fatty acid amides, which tend to color the product yellow.
- An ideal liquid detergent is also one where the major ingredients are highly compatible with each other so that only a minimum amount of solubilizing agent is needed to keep the detergent in a single phase, yet many detergent surface active agents and suds builders are not unlimitedly soluble in water, especially in combination with each other.
- Products containing fatty acid amides are especially subject to phase separation as a result of exposure to low temperatures (poor freeze resistance) and therefore require considerable amounts of a solubilizing agent such as ethyl alcohol or sodium toluene sulfonate.
- a solubilizing agent such as ethyl alcohol or sodium toluene sulfonate.
- the ideal liquid detergent weould be suitable for effective and high sudsing use with all kinds of soil and wash water, including acidic soil and wash water.
- the unbuilt, high-sudsing, light-duty liquid detergent compositions of this invention consist essentially of: (1) from about to about 35% by weight of the composition of a sulfate detergent surfactant having the following formula wherein R is a straight chain alkyl group having from.
- a viscosity control agent such as either potassium, sodium, or ammonium toluene sulfonate or potassium, sodium or ammonium xylene sulfonate, and mixtures thereof; perfume; opacifiers; and coloring can be added if desired but are not necessary.
- the composition is not a stable, single-phase system.
- this ratio is more than about 6/1, the suds building ability of the primary sultaine is not adequately realized.
- the total amount of both sulfate detergent surfactant and primary sultaine should not be more than about 40% by weight of the composition in order to insure formation of a stable, single-phase system; but the total amount should be more than about 20% by weight of the composition to provide sufiicient suds and detergency.
- the concentration range of the sulfate detergent agent is set at the lower limit of 15% by weight of the composition by sudsing considerations and at the upper limit of 35% by weight of the composition by viscosity consideratrons. At lower levels the quantity of suds is drastically reduced and at higher levels the products is no longer pourable.
- Both the sulfate detergent and the primary sultaine have certain requirementsas to structure.
- the alkyl chain lengths in both should not be less than ten carbon atoms since compounds having shorter chain lengths give reduced detergency. Similarly, the alkyl chain lengths should not be greater than 14 since compounds having longer chain lengths produce reduced quantities of suds.
- the requirement that at least of the alkyl chains in both of the compounds contain 12 carbon atoms is determined by the above considerations of sudsing and detergency since this is the optimum chain length.
- a desirable alkyl chain length distribution is obtained from the middle out of distilled coconut fatty alcohol as more fully described in Example I.
- a sulfate detergent containing no ethylene oxide groups is an effective detergent and sudser, but is not quite as mild as a. sulfate detergent surfactant containing these groups. However, a sulfate detergent with more than about four ethylene oxide groups in the molecule has substantially reduced sudsing capacity.
- the preferred sulfate detergent surfactant contains an average of three ethylene oxide groups per molecule. In general, all of the compositions of this invention are mild when applied to human skin.
- the swltones used in preparing the primary sultaines of this invention contain carbon chains of either three or four carbon atoms and have the following general formula:
- R is a carbon chain of either four or three carbon atoms.
- Su-ltones with less than three carbon atoms are not available and reaction products prepared with sultones having more than four carbon atoms are less effective with respect to suds building ability both as to quantity and stability, but primarily with respect to quantity.
- the preparation of such reaction products can be accomplished by reacting equimolar quantities of the primary amine and the sultone in acetone while refluxing at the boiling point of acetone. The precipitate which forms can then be recrystallized from acetone if desired.
- the structure of this reaction product is not known and consequently the product can only be described in terms of the reaction.
- the finished detergent compositions of this invention require the addition of a solubilizing agent to prevent phase separation Although much less solubilizer is needed in the compositions of this invention than in those which use an amide suds builder, still at least about 10% of the solubilizing agent is necessary. Too much solubilizing agent would be costly and might adversely affect viscosity, so that preferably only enough solubilizing agent is included in the composition to keep the composition in a pourable single phase under conditions of use, but not more than about 25% by weight of the composition.
- various minor ingredients including perfume, viscosity control agents, opacifiers, and coloring can be added.
- Inert materials such as water-soluble inorganic salts may also be present in amounts up to about 12% by weight of the composition, generally as impurities from the various other ingredients or as opacifier stabilizers.
- Potassium toluene sulfonate as a viscosity control agent, is a desirable minor additive in amounts up to It increases the viscosity of the compositions.
- sirable additives include opacifiers such as ethylene glycol distearate or polystyrene in amounts up to about 3% by weight of the composition.
- compositions of this invention need not contain conventional suds builders such as fatty acid amides.
- the superior sudsing ability of these compositions makes it unnecessary to have such suds builders present, which results in cost advantages and simplified formulation.
- compositions of this invention have better odor Other de-' product of a primary amine having a carbon chain length distribution of C10, C12, C14, and C16, and a propane sultone, the primary sultaine being prepared by reacting equimolar quantities of amine and sultone in acetone solution while refluxing at the boiling point of acetone, and recrystallizing the resulting precipitate from acetone.
- Each composition also contained 10% ethyl alcohol. Diiferent detergent surfactants were added to these compositions in varying amounts.
- Detergent surfactant A was the ammonium salt of the su-lf ated condensation product of middle-cut coconut alcohol, containing approximately 2% C 66% C 23% C and 9% C of alkyl groups, with three moles of ethylene oxide (NH AE S).
- Detergent surfactant B was the sodium salt of tetrapropylene benzene sulfonate (NaABS)
- Detergent surfiactant C was the sodium salt of the sulfated condensation product of A (NaAE S).
- Detergent surfactant D was the ammonium salt of the sulf-ated condensation product of tetnapropylene phenol and four moles of ethylene oxide (NH APE S). The balance of each composition was water. All percentages contained herein are by weight of the composition.
- compositions of this invention are not distinguished from compositions outside the scope of the invention by virtue of being the only operable combinations, but uather by the exceptional improvement in performance effected by the compositions of this invention.
- compositions of this invention have improved freeze resistance as compared with compositions containing amides.
- Example I The following compositions (with the exception of As can be seen from the performance of these compositions neither all primary sultaine (Composition 1) nor all alkyl ethylene oxide sulfate (Composition '9) forms a good sudsing product when used alone, but when these materials are used together as in Compositions 6 Composition 9) contained varying amounts of the reaction outstanding liquid products of this invention.
- opacifiers such as ethylene glycol distearate, and/or as much as 5% of either sodium, potassium, or ammonium toluene sulfonate or sodium, potassium, or ammonium Xylene sulfonate, and mixtures thereof (as viscosity control agents) are added to the Compositions 6 and 8, substantially equivalent results are obtained.
- alkyl sulfates and alkyl ethylene oxide sulfates having different numbers of ethylene oxide groups, on the average, in the molecule are substituted for the alkyl ethylene oxide sulfates of Compositions 6 and 8, substantially equivalent results are obtained.
- a high-sudsing, light-duty liquid detergent composition consisting essentially of (1) from about 15% to about 35% by weight of the composition of a sulfate detergent having the following formula wherein R represents straight chain alkyl groups having from about to about 14 carbon atoms with at least 50% of said alkyl groups having 12 carbon atoms, x is a number from 0 to about 4, and Me is selected from the group consisting of sodium, potassium, ammonium, and triethanol ammonium cations; (2) from about 3% to about 8% by weight of the composition of the reaction product of a primary amine having a straight chain alkyl group having from 10 to 14 carbon atoms with at least 50% of said alkyl groups having 12 carbon atoms and a sultone having from 3 to 4 carbon atoms, said reaction product corresponding to that prepared by reacting equimolar quantities of said amine and said sultone in acetone solution While refluxing at the boiling point of acetone; (3) from about 10% to about 25% of a solub
- composition of claim 1 containing, as an additional ingredient, a viscosity control agent selected from the group consisting of sodium, potassium, and ammonium toluene sulfonates, sodium, potassium, and ammonium Xylene sulfonates, and mixtures thereof in an amount up to about five percent by weight of the composition.
- a viscosity control agent selected from the group consisting of sodium, potassium, and ammonium toluene sulfonates, sodium, potassium, and ammonium Xylene sulfonates, and mixtures thereof in an amount up to about five percent by weight of the composition.
- composition of claim 1 wherein the sulfate detergent is the ammonium salt of the sulfated condensation product of one mole of middle-cut coconut alcohol and three moles of ethylene oxide.
Landscapes
- 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 |
---|---|---|---|
NL286286D NL286286A (is") | 1961-12-15 | ||
US159770A US3211661A (en) | 1961-12-15 | 1961-12-15 | Liquid detergent composition |
FR918691A FR1449570A (fr) | 1961-12-15 | 1962-12-14 | Composition détersive liquide améliorée |
GB47511/62A GB990696A (en) | 1961-12-15 | 1962-12-17 | Detergent composition |
BE655485D BE655485A (is") | 1961-12-15 | 1964-11-09 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US159770A US3211661A (en) | 1961-12-15 | 1961-12-15 | Liquid detergent composition |
Publications (1)
Publication Number | Publication Date |
---|---|
US3211661A true US3211661A (en) | 1965-10-12 |
Family
ID=22573945
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US159770A Expired - Lifetime US3211661A (en) | 1961-12-15 | 1961-12-15 | Liquid detergent composition |
Country Status (4)
Country | Link |
---|---|
US (1) | US3211661A (is") |
BE (1) | BE655485A (is") |
GB (1) | GB990696A (is") |
NL (1) | NL286286A (is") |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3862050A (en) * | 1971-06-30 | 1975-01-21 | Procter & Gamble | Sodium alkyl ether sulfate c{hd 12{b -c{hd 14 {b soap blends for optimum sudsing in hard surface cleaners |
US4983323A (en) * | 1989-04-12 | 1991-01-08 | Vista Chemical Company | Surfactant compositions |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA734138B (en) * | 1972-07-20 | 1975-01-29 | Colgate Palmolive Co | Heavy duty liquid laundry detergent |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1944300A (en) * | 1930-05-12 | 1934-01-23 | Ig Farbenindustrie Ag | Aliphatic amine sulphonic acid containing eight or more carbon atoms |
US2673842A (en) * | 1954-03-30 | Detergent compositions | ||
US2809973A (en) * | 1954-11-12 | 1957-10-15 | Monsanto Chemicals | Sodium 3-(2-benzothiazolylmercapto)-1-propane sulfonate |
DE1018421B (de) * | 1952-10-03 | 1957-10-31 | Boehme Fettchemie Gmbh | Verfahren zur Herstellung von Sulfobetainen |
US2941950A (en) * | 1954-09-30 | 1960-06-21 | Procter & Gamble | Concentrated liquid detergent |
US2970963A (en) * | 1958-04-23 | 1961-02-07 | Procter & Gamble | Opaque liquid detergent composition |
-
0
- NL NL286286D patent/NL286286A/xx unknown
-
1961
- 1961-12-15 US US159770A patent/US3211661A/en not_active Expired - Lifetime
-
1962
- 1962-12-17 GB GB47511/62A patent/GB990696A/en not_active Expired
-
1964
- 1964-11-09 BE BE655485D patent/BE655485A/xx unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2673842A (en) * | 1954-03-30 | Detergent compositions | ||
US1944300A (en) * | 1930-05-12 | 1934-01-23 | Ig Farbenindustrie Ag | Aliphatic amine sulphonic acid containing eight or more carbon atoms |
DE1018421B (de) * | 1952-10-03 | 1957-10-31 | Boehme Fettchemie Gmbh | Verfahren zur Herstellung von Sulfobetainen |
US2941950A (en) * | 1954-09-30 | 1960-06-21 | Procter & Gamble | Concentrated liquid detergent |
US2809973A (en) * | 1954-11-12 | 1957-10-15 | Monsanto Chemicals | Sodium 3-(2-benzothiazolylmercapto)-1-propane sulfonate |
US2970963A (en) * | 1958-04-23 | 1961-02-07 | Procter & Gamble | Opaque liquid detergent composition |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3862050A (en) * | 1971-06-30 | 1975-01-21 | Procter & Gamble | Sodium alkyl ether sulfate c{hd 12{b -c{hd 14 {b soap blends for optimum sudsing in hard surface cleaners |
US4983323A (en) * | 1989-04-12 | 1991-01-08 | Vista Chemical Company | Surfactant compositions |
Also Published As
Publication number | Publication date |
---|---|
GB990696A (en) | 1965-04-28 |
BE655485A (is") | 1965-05-10 |
NL286286A (is") |
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