US3179599A - Detergent composition - Google Patents
Detergent composition Download PDFInfo
- Publication number
- US3179599A US3179599A US121341A US12134161A US3179599A US 3179599 A US3179599 A US 3179599A US 121341 A US121341 A US 121341A US 12134161 A US12134161 A US 12134161A US 3179599 A US3179599 A US 3179599A
- Authority
- US
- United States
- Prior art keywords
- weight
- composition
- ammonium
- sodium
- sudsing
- 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
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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/16—Sulfonic acids or sulfuric acid esters; Salts thereof derived from divalent or polyvalent alcohols
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/83—Mixtures of non-ionic with anionic 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0094—High foaming compositions
-
- 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
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/75—Amino oxides
Definitions
- An ideal liquid detergent is also one where the major ingredients are highly compatible 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. Furthermore, the ideal liquid detergent would be suitable for use with all kinds of soil and wash water, including acid soil and wash Water.
- the unbuilt, high-sudsing, light-duty liquid detergent compositions of this invention consist essentially of: (1) from about 20% to about 40% by weight of the composition of a sulfate detergent surfactant having the following formula .having 12 carbon atoms and two short chain alkyl groups having from one to about two carbon atoms in an amount such that the weight ratio of sulfate detergent surfactant to amine oxide is from about 1/1 to about 7/1; (3) from about 2% to about 10% by Weight of the composition of an alkyl glyceryl ether sulfonate having a straight chain alkyl group having from about 10 to about 14 carbon atoms with at least 50% of said alkyl groups having 12 carbon atoms, the cation of said sulfonate being selected from the group consisting of monoethanolamine, diethanolamine, triethanolamine, ammonium, sodium and potassium cations and mixtures thereof, the amount of said sulfonate being at least 20% of the amount of said amine oxide; (4)
- a viscosity control agent such as either potassium, sodium, or ammonium toluene sulfonate or potassium, sodium or ammonium xylene sulfonate; perfume; opacifiers; and coloring can be added.
- the amine oxides of this invention build (enhance) the sudsing ability of the sulfates of this invention to a high degree, but do not build the sudsing ability of the sulfonates, or sulfate surfactants containing aromatic configurations to the extent desired in light duty detergents having a pH in the range of 6.5 to 9.0.
- sudsing ability refers to both the initial quantity of suds and the persistence of the suds throughout the Washing operation.
- the persistence (stability) of the suds of the composition of this invention is extremely good under alkaline, neutral, and acidic conditions. It has also been discovered (as set forth in the copending application of Norman R.
- compositions with Weight ratios of sulfate surfactant to amine oxide greater than 7/1 lose sudsing ability both in acid and neutral wash Water.
- This sudsing sensitivity of combinations of sulfate surfactant and amine oxide to acid conditions can be controlled very satisfactorily by the inclusion in the composition of from about 2% to about 10% by weight of the composition of a monoethanolamine, diethanolarnine, triethanolamine, sodium, potassium, or ammonium alkyl glyceryl ether sulfonate as hereinbefore described.
- the addition of this sulfonate permits the usage of sulfate surfactant to amine oxide ratios of from about 1/1 about 7/ 1.
- the sulfonate not only permits the use of sulfate surfactant to amine oxide ratios of less than 3/1 under acid conditions, it also increases sudsing performance for almost all ratios of sulfate surfactant to amine oxide within the broad range hereinbefore mentioned. This is a very surprising result since a composition containing only the alkyl glyceryl ether sulfonate and amine oxide in an unbuilt product, does not perform as satisfactorily as the sulfate alone as far as sudsing ability is concerned under either acidic or neutral conditions. Only in ternary mixtures as hereinbefore described, do the alkyl glyceryl ether sulfonates of this invention have a synergistic effect upon sudsing ability.
- weight ratios of sulfate surfactant to amine oxide of less than l/l are preferably not used from the standpoint of mildness, and there is a loss in sudsing performance with ratios above 7/1, even with the inclusion of the sulfonates of this invention.
- the loss of sudsing ability under acid conditions is ordinarilymanifested only in unbuilt detergents.
- the pH of a liquid detergent built with substantial quantities of ordinary phosphate builders and/ or silicate salts and/ or other alkaline builders is around 10 or above
- the pH of the unbuilt liquid detergents of this invention and of unbuilt liquid detergents in general is about 6.5 to 9.0
- the builder provides a reservoir of alkalinity so that there taining these groups.
- the sulfonate should be present in an amount equal to at least about by Weight of the amount of amine oxide present. This amount is required to give satisfactory sudsing performance under acid conditions. From an economic standpoint, the ratio of amine oxide to alkyl glyceryl ether sulfonate should not be less than about 1/1 since an increase in the amount of sulfonate above the amount represented by this ratio does not give appreciably better performance.
- concentration range of sulfate detergent surfactant is set at the lower limit of 20% by sudsing considerations and at the upper limit of by viscosity considerations.
- the sulfate detergent surfactant itself has certain requirements as to the length of the alkyl chain. Chain lengths of less than ten carbon atoms give reduced detergency and sudsing and chain lengths greater than 14 reduce the quantity of suds which are produced. Somewhat the same considerations apply also to the chain length of the long alkyl group in the amine oxide surfactant.
- the length of the short alkyl groups in the amine oxide is set by considerations of solubility. Groups which are longer than about two carbon atoms inhibit the solubility of the amine oxide in the water.
- a sulfate detergent surfactant containing no ethylene oxide groups is an effective detergent and sudser, but is not quite as mild as a sulfate detergent surfactant con- However, more than about four ethylene oxide groups in the molecule will substantially reduce 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 finished composition requires'the addition of a solubilizing agent to prevent phase separation. Although much less solubilizer is needed when an amide is not present, still at least about 5% of the solubilizing agent is necessary. Too much solubilizing agent would be too costly and tends to adversely affect viscosity, so that only enough solubilizing'agent should be included in the composition to keep the composition in a pourable single phase under conditions of use, but not more than about 40% by weight of the composition.
- the toluene sulfonates and xylene suhonates hereinbefore described are desirable minor additives in amounts up to 5%. They increase the viscosity of the compositions.
- Other desirable additives include opacifiers such as ethylene glycol distearate or polystyrene in amounts up to about 3% by weight of the compositions.
- compositions of this invention do not contain conventional suds builders such as 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.
- the most common suds builders are amides, which have odors and which color the product, the compositions of this invention have better odor and better color than many prior high sudsing compositions.
- Amides also tend to cause phase instability which can only be'corrected by adding much more solubilizing agent than is ordinarily required in compositions of this invention.
- Example I The following compositions contained varying amounts of the ammonium salt of the sulfated condensation product of one mole of middle-cut coconut alcohol containmg 1t 12, 14; and 9%C16 alkyl groups with three moles of ethylene oxide (A), a tertiary amine oxide having a long alkyl chain derived from the same middle-out coconut alcohol and two methyl groups (B), and sodium alkyl glyceryl ether sulfonate wherein the alkyl group is derived from the same middle-cut coconut alcohol (C).
- the compositions also contained 10% ethyl alcohol and the balance water. All percentages contained herein are by weight of the composition.
- the foam height after washing each set was expressed in terms -of percent of original suds height and an average of the Composition 1 2 3 4 5 6 7 8 9 10 Percent A 25 25 25 25 25 25 20 20 20 20 20 Percent B 5 5 5 5 5 5 5 5 5 5 Percent C 0 1 2 3 4 0 1 2 3 4 Percent Ethyl alcohoL 10 10 10 10 10 1O 10 10 10 Percent Water bal. bal. bal. bal. bal. bal. bal. bal. bal.
- compositions with weight ratios of sulfate detergent surfactant to amine oxide of more than 3/1 all have acceptable sudsing performance.
- compositions without sodium alkyl glyceryl ether sulfonate (Compositions 1 and 6) did not perform as well relative to sudsing as those compositions containing sulfonate (Compositions 2-5 and 7-10).
- compositions with a weight ratio of sulfate detergent surfactant to amine oxide of less than 3/1 did not perform well at all under acid conditions when there was no sulfonate present (Compositions 11, 16 and 19), but performed exceptionally when there was even a small amount of sulfonate present (Compositions 12- 14, 17, 18, and 20).
- Example ll A detergent composition was prepared containing 25% by weight of the composition of the sulfate detergent surfactant of Example I, 5% by weight of the composition of the amine oxide of Example I, 2% by weight of the composition of the alkyl glyceryl ether sulfonated of Example I, 1% by weight of the composition of ammcnium phosphate, 12% by weight of the composition of ethyl alcohol, 0.3% by weight of the composition of perfume, 0.2% by weight of the composition of a 1% by weight color solution, 0.1% by weight of the composition of citric acid, and the balance water.
- This composition was tested under typical home use conditions and found to be a very satisfactory high-sudsing, light-duty liquid detergent under alkaline, neutral, and acidic conditions.
- the ammonium phosphate present in this and subsequent examples is present only in small amounts for the purpose of adjusting the pH of the product and is not present. as a builder.
- sulfate and sulfonate detergent surfactants in the preceding example are the monoethanolamine, diethanolamine, triethanolamine, or potassium salts, substantially equivalent results are achieved.
- Example 111 A detergent composition was prepared containing 25% of the sulface detergent surfactant of Example I, 5% of the amine oxide of Example I, 4% sodium alkyl glyceryl ether sulfonate wherein the alkyl group is derived from the same middle-cut coconut alcohol as the sulfate, 2% potassium toluene sulfonate 6% ethyl alcohol, 2% potassium chloride, 1% ethylene glycol distearate, 0.1% critic acid, 0.15% perfume, 0.09% brightener, and the balance water. All percentages herein are by weight of the composition. The composition was tested under home use conditions and found to be an effective highsudsing, light-duty liquid detergent under alkaline, neutral and acidic conditions.
- Example IV A detergent composition was prepared containing 25 of the sodium salt of the sulfated condensation product of one mole of middle-cut coconut alcohol, as hereinbefore described, and three moles of ethylene oxide; 6% lauryl dimethyl amine oxide; 4% sodium alkyl glyceryl ether sulfonate wherein the alkyl group is derived from middle-cut coconut alcohol as hereinbefore described; 3% sodium alkyl glyceryl ether sulfonate wherein the alkyl group was derived from tallow; 12% sodium nitrate; 8% ethyl alcohol; 2% sodium toluenesulfonate; 0.15% perfume; and the balance water and miscellaneous inert in- Example V
- a detergent composition was prepared containing 21% of the sulfate detergent surfactant of Example I, 4% of the amine oxide of Example I, 2% of the alkyl glyceryl ether sulfonate of Example I, 1% ammonium
- An unbuilt, high-sudsing, light-duty liquid detergent composition having a pH of from about 6.5 to 9.0 and having special utility under acid conditions such as might exist where the pH of the wash water is less than about 6.5 and consisting essentially of (1) from about 20% to about 40% by weight of the composition of a sulfate detergent having the following formula wherein R is a straight chain alkyl group having from about 10 to about 14 carbon atoms with at least 50% of said alkyl groups having 12 carbon atoms, x is a number from zero to about four, and Me is selected from the group consisting of monoethanolamine, diethanolamine, triethanolamine, ammonium, sodium, and potassium cations; (2) a trialkyl amine oxide having one straight chain alkyl group having from about 10' to about 14 carbon atoms, with at least 50% of said alkyl groups having 12 carbon atoms, and two short chain alkyl groups having from one to about two carbon atoms, in an amount suflicient to give a ratio of sulf
- the cation of said sulfonate being selected from the group consisting of monoethanolamine, diethanolamine, triethanolamine, ammonium, sodium, and potassium cations and mixtures thereof, the amount of said sulfonate being at least 20% of the amount of said amine oxide; (4) at least about 5% but not more than about 40% by weight of the composition of a solubilizing agent selected from the group consisting of methyl, ethyl, n-propyl, and isopropyl alcohols, and mixtures thereof; and (5) the balance water.
- composition of claim 1 containing from zero to about five percent of material selected from the group consisting of sodium, potassium, and ammonium toluene sulfonates; sodium, potassium, and ammonium xylene sulfonates; and mixtures thereof.
- composition of claim 1 wherein the sulfate detergent is the ammonium salt of the sulfate of the condensation product of one mole of middle-cut coconut alcohol and an average of three moles of ethylene oxide.
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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 (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL280455D NL280455A (xx) | 1961-07-03 | ||
NL136443D NL136443C (xx) | 1961-07-03 | ||
US121341A US3179599A (en) | 1961-07-03 | 1961-07-03 | Detergent composition |
FR902574A FR1442257A (fr) | 1961-07-03 | 1962-06-29 | Composition détergente améliorée |
DK294462A DK106810C (da) | 1961-07-03 | 1962-06-30 | Finvaskemiddelblanding. |
DE19621467644 DE1467644A1 (de) | 1961-07-03 | 1962-07-03 | Neue Reinigungsmittel |
SE7432/62A SE309819B (xx) | 1961-07-03 | 1962-07-03 | |
GB25453/62A GB993031A (en) | 1961-07-03 | 1962-07-03 | Detergent composition |
BE649886D BE649886A (xx) | 1961-07-03 | 1964-06-29 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US121341A US3179599A (en) | 1961-07-03 | 1961-07-03 | Detergent composition |
FR902574A FR1442257A (fr) | 1961-07-03 | 1962-06-29 | Composition détergente améliorée |
IT1316662 | 1962-07-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3179599A true US3179599A (en) | 1965-04-20 |
Family
ID=27246658
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US121341A Expired - Lifetime US3179599A (en) | 1961-07-03 | 1961-07-03 | Detergent composition |
Country Status (7)
Country | Link |
---|---|
US (1) | US3179599A (xx) |
BE (1) | BE649886A (xx) |
DE (1) | DE1467644A1 (xx) |
FR (1) | FR1442257A (xx) |
GB (1) | GB993031A (xx) |
NL (2) | NL136443C (xx) |
SE (1) | SE309819B (xx) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4953610A (xx) * | 1972-09-25 | 1974-05-24 | ||
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 |
US3951596A (en) * | 1972-10-13 | 1976-04-20 | Colgate-Palmolive Company | Soap curd dispersant |
US3992146A (en) * | 1971-09-13 | 1976-11-16 | Fazzalari Frank A | Process of using biocidal solutions containing copper sulfate |
US4259216A (en) * | 1979-10-11 | 1981-03-31 | The Lion Fat & Oil Co., Ltd. | Process for producing liquid detergent composition |
DE3016544A1 (de) * | 1980-04-29 | 1981-11-05 | Lanko, Inc., Philadelphia, Pa. | Emulsionen |
US4304680A (en) * | 1973-02-05 | 1981-12-08 | Colgate-Palmolive Company | Laundry soap |
US5310508A (en) * | 1992-07-15 | 1994-05-10 | Colgate-Palmolive Company | Mild personal cleansing compositions containing sodium alcohol ethoxy glyceryl sulfonate |
US5783200A (en) * | 1997-01-21 | 1998-07-21 | The Procter & Gamble Company | Personal cleansing compositions |
US6096697A (en) * | 1997-01-21 | 2000-08-01 | The Procter & Gamble Company | Personal cleansing compositions providing improved hair and skin conditioning |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2082249A5 (xx) * | 1970-03-09 | 1971-12-10 | Colgate Palmolive Co | |
ZA734138B (en) * | 1972-07-20 | 1975-01-29 | Colgate Palmolive Co | Heavy duty liquid laundry detergent |
WO2017208038A1 (en) * | 2016-05-31 | 2017-12-07 | MAKÁNNÉ OSKOVICS, Andrea | C-s-f engine block cleaning liquid emulsion suitable for cleaning oily contaminations off the surfaces of all kinds of machinery, equipment and parts, furthermore suitable for dissolving crude oil from the surfaces of the seas, beaches, animals and plants |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2060568A (en) * | 1934-06-23 | 1936-11-10 | Soc Of Chemical Ind | Assisting agents for the textile industry |
US2169976A (en) * | 1934-01-26 | 1939-08-15 | Ig Farbenindustrie Ag | Process of producing assistants in the textile and related industries |
US2310074A (en) * | 1938-05-05 | 1943-02-02 | Unichem Chemikalien Handels A | Treatment bath |
US2607740A (en) * | 1950-05-03 | 1952-08-19 | Colgate Palmolive Peet Co | Liquid anionic-dialkylolamide detergent composition |
US2861956A (en) * | 1953-02-25 | 1958-11-25 | Monsanto Chemicals | Liquid detergent compositions |
US2877185A (en) * | 1956-06-29 | 1959-03-10 | Procter & Gamble | Clear liquid detergent composition |
US2999068A (en) * | 1959-04-27 | 1961-09-05 | Procter & Gamble | Personal use detergent lotion |
US3001945A (en) * | 1959-04-29 | 1961-09-26 | Procter & Gamble | Liquid detergent composition |
-
0
- NL NL280455D patent/NL280455A/xx unknown
- NL NL136443D patent/NL136443C/xx active
-
1961
- 1961-07-03 US US121341A patent/US3179599A/en not_active Expired - Lifetime
-
1962
- 1962-06-29 FR FR902574A patent/FR1442257A/fr not_active Expired
- 1962-07-03 DE DE19621467644 patent/DE1467644A1/de active Pending
- 1962-07-03 SE SE7432/62A patent/SE309819B/xx unknown
- 1962-07-03 GB GB25453/62A patent/GB993031A/en not_active Expired
-
1964
- 1964-06-29 BE BE649886D patent/BE649886A/xx unknown
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2169976A (en) * | 1934-01-26 | 1939-08-15 | Ig Farbenindustrie Ag | Process of producing assistants in the textile and related industries |
US2060568A (en) * | 1934-06-23 | 1936-11-10 | Soc Of Chemical Ind | Assisting agents for the textile industry |
US2310074A (en) * | 1938-05-05 | 1943-02-02 | Unichem Chemikalien Handels A | Treatment bath |
US2607740A (en) * | 1950-05-03 | 1952-08-19 | Colgate Palmolive Peet Co | Liquid anionic-dialkylolamide detergent composition |
US2861956A (en) * | 1953-02-25 | 1958-11-25 | Monsanto Chemicals | Liquid detergent compositions |
US2877185A (en) * | 1956-06-29 | 1959-03-10 | Procter & Gamble | Clear liquid detergent composition |
US2999068A (en) * | 1959-04-27 | 1961-09-05 | Procter & Gamble | Personal use detergent lotion |
US3001945A (en) * | 1959-04-29 | 1961-09-26 | Procter & Gamble | Liquid detergent composition |
Cited By (11)
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 |
US3992146A (en) * | 1971-09-13 | 1976-11-16 | Fazzalari Frank A | Process of using biocidal solutions containing copper sulfate |
JPS4953610A (xx) * | 1972-09-25 | 1974-05-24 | ||
JPS5143483B2 (xx) * | 1972-09-25 | 1976-11-22 | ||
US3951596A (en) * | 1972-10-13 | 1976-04-20 | Colgate-Palmolive Company | Soap curd dispersant |
US4304680A (en) * | 1973-02-05 | 1981-12-08 | Colgate-Palmolive Company | Laundry soap |
US4259216A (en) * | 1979-10-11 | 1981-03-31 | The Lion Fat & Oil Co., Ltd. | Process for producing liquid detergent composition |
DE3016544A1 (de) * | 1980-04-29 | 1981-11-05 | Lanko, Inc., Philadelphia, Pa. | Emulsionen |
US5310508A (en) * | 1992-07-15 | 1994-05-10 | Colgate-Palmolive Company | Mild personal cleansing compositions containing sodium alcohol ethoxy glyceryl sulfonate |
US5783200A (en) * | 1997-01-21 | 1998-07-21 | The Procter & Gamble Company | Personal cleansing compositions |
US6096697A (en) * | 1997-01-21 | 2000-08-01 | The Procter & Gamble Company | Personal cleansing compositions providing improved hair and skin conditioning |
Also Published As
Publication number | Publication date |
---|---|
NL136443C (xx) | |
NL280455A (xx) | |
DE1467644A1 (de) | 1969-10-09 |
GB993031A (en) | 1965-05-26 |
SE309819B (xx) | 1969-04-08 |
BE649886A (xx) | 1964-10-16 |
FR1442257A (fr) | 1966-06-17 |
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