US3310499A - Novel detergent compositions - Google Patents
Novel detergent compositions Download PDFInfo
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- US3310499A US3310499A US297974A US29797463A US3310499A US 3310499 A US3310499 A US 3310499A US 297974 A US297974 A US 297974A US 29797463 A US29797463 A US 29797463A US 3310499 A US3310499 A US 3310499A
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- salt
- amine
- sulfonic acid
- mahogany sulfonate
- parts
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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
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
- D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
- D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
Definitions
- This invention is concerned with novel detergent compositions. More specifically, it relates to a detergent composition adapted for incorporation into a non-polar organic dry-cleaning solvent comprising alkali metaland/ or alkaline-earth metal mahogany sulfonates and certain monoalkanolamine salts of alkyl arylsulfonic acids.
- Mahogany sulfonates have ben employed to improve dry-cleaning solvents. Improved detergency and soil dispersion properties of the latter solvents have been observed. Unfortunately, such additives impart to the drycleaning solvent relatively poor water solubilizing properties. Possession of water solubilizing characteristics of detergent additives is of significant consequence, for otherwise the presence of excess water in the solventdetergent system can damage irreparably a garment to be treated. If the detergent additive could be modified so as to impart water-binding properties to an otherwise good detergent without impairing the latters effectiveness, such a product would be highly desirable.
- neutralization of an alkylaryl sulfonic acid with an alkanol amine is performed in the presence of the alkali metal salt of an oil soluble mahogany sulfonic acid or mixtures thereof.
- the desired enhanced detergency is realized when the neutralization of the alkyl aryl sulfonic acid by means of the amine is carried out in the presence of the mahogany sulfonate.
- a good practice is to incorporate about 1 part of alkali metal or alkaline earth metal mahogany sulfontae in about 0.5 part to about 1.5 part, on a weight basis, of the aforementioned amine salt, and about equal parts of each of the sulfonate and the amine salt are preferred.
- any commercially available oil-soluble mahogany sulfonate having an average molecular weight of at least 425 can be employed herein. It is advantageous to employ a alkalimetal salt of mahogany sulfonic acid, such as the sodium, potassium or lithium salt, although the alkaline earth metal salt, such as the calcium or baroetyl benzene sulfonic acid, nonyl benzene sulfonic acid, decyl benzene sulfonic acid, undecyl benzene sulfonic acid,
- a alkalimetal salt of mahogany sulfonic acid such as the sodium, potassium or lithium salt
- the alkaline earth metal salt such as the calcium or baroetyl benzene sulfonic acid, nonyl benzene sulfonic acid, decyl benzene sulfonic acid, undecyl benzene sulfonic acid,
- dodecyl benzene sulfonic acid dodecyl benzene sulfonic acid, lauryl benzene sulfonic acid, tridecyl benzene sulfonic acid, myristyl benzene sulfonic acid, hexadecyl benzene sulfonic acid, octadecyl benzene sulfonic acid, l-dodecyl naphthylsulfonic acid, and fl-myristyl naphthylsulfonic acid.
- Exemplary monoalkanol amines utilized in the neutralization of the alkyl aryl sulfonic acid are the following monohydroxy lower alkyl amines:
- Mono-ethanol amine Mono-n-propanol amine, Mono-isopropanol amine, Mono-n-butanol amine, Mono-isobutanol amine, and Mono-pentanol amine.
- the detergent compositions prepared by admixing the alkylaryl' sulfonic acid with the mahogany sulfonate salt and the mixture neutralized with the appropriate mono-' alkanol amine, can be incorporated into a non-polar solvent, such as Stoddards solvent, petroleum ether, deodorized kerosene, and mineral spirits.
- a non-polar solvent such as Stoddards solvent, petroleum ether, deodorized kerosene, and mineral spirits.
- the amine is added to a mixture of the alkyl aryl sulfonic acid and the salt of the mahogany sulfonate until a pH between 6.5 and 9.5 is obtained, and preferably between 7.0 and 8.5. At this point, an amber colored, viscous stable solution is noted.
- inert solvents are for instance:
- Example 1 To a suitable reaction vessel are admixed 44 parts of sodium mahogany sulfonate, 56 parts of mineral oil and 44 parts of dodecyl benzene sulfonic acid. To the mixture is next added 12 parts of mono-isopropanolamine. Resultant mixture obtained is found to have a pH equal to 7.5. T
- Example 2 Into an appropriate reaction vessel are added 22 parts of calcium mahogany sulfonate, 56 parts of deodorized kerosene and 44 parts of dodecylbenzenesulfonic acid. The mixture is then admixed. Twelve (12) parts of monoisop-ropanol amine are then added and gently stirred. A terminal pH of 7.8 is obtained.
- Example 3 T o 22 parts of sodium mahogany sulfonate, 22 parts of calcium mahogany sulfonate and 44 parts of dodecylbenzenesulfonic acid in 56 parts of petroleum ether are added while stirring 12 parts of monoisopropanol amine. The mixture is then found to possess a pH of about 8.
- Example 4 A mixture of 22 parts of sodium mahogany sulfonate and 22 parts of calcium mahogany sulfonate, 40 parts TABLE I Percent Percent Percent Percent Detergeney Redeposition Water Solvent Ex. Detergent in Stoddard Solvent Sgluble R.H.
- Enhanced detersive properties of the compositions illustrated in the table below are determined in the conventional manner involving the use of a launderometer as described in the AATCC Yearbook for 1955 at page 55.
- a standard soiled swatch and stainless steel balls together with a non-polar drycleaning solvent, containing 1% by weight of the detergent additive mixture as prepared by each of the above examples are added to a lannderometer jar. After a twenty minute wash cycle, the washed swatch is removed from the jar, and dried to remove the solvent. Reflectance readings before and after washing of the soiled and unsoiled swatches are taken and recorded in percent detergency and percent redeposition, respectively.
- the initial reflectance readings of the cotton and wool swatches used are: 103 and 93, respectively.
- Percent detergency is determined by subtracting the reflectance reading of the soiled swatch and dividing this differonce by the difference between the initial unsoiled swatch reflectance reading and soiled reflectance reading, multiplied by 100.
- the percent detergency for cotton is:
- R is the reflectance reading of the soiled swatch after drycleaning.
- the redeposition value in percent for cotton is similarly represented by the formula:
- R is the reflectance reading of unsoiled swatches after drycleaning.
- percent detergency and percent redeposition are determined in perchloroethylene solvent.
- a visual water tolerance value (V.W.T.V.) of an oil soluble detergent is a measurement of the amount of water that the detergent will hold or otherwise dissolve in solvent, such as perchloroethylene.
- Water tolerance value herein is obtained byvisual measurements in the formula below by adding water to a known amount of detergent dissolved in solvent until the solution shows a definite cloudiness:
- compositions of the present invention exhibit synergistic properties with respect to sweet-stain removal.
- compositions of the present invention exhibit a markedly higher water binding effect than do the mahogany sulfonates. This property is related directly to the maintenance of a low or safe solvent relative humidity.
- a non-polar solvent compatible detergent composition consisting essentially of: i
- a non-polar solvent compatible detergent composition consisting essentially of:
- monoisopropanol amine salt monoalkanol amine salt is of tride-cylbenzenesulfonic acid.
- a process for preparing an oil-soluble, detergent composition which consists essentially in the steps of: admixing in the presence of a salt of an oil-soluble mahogany sulfonate having an average molecular weight of at least 425, said salt being selected from the group consisting of alkali metal, alkaline earth metal and mixtures thereof, (a) a higher alkyl aryl sulfonic acid and (b) monohydroxy lower alkyl until a pH between about 6.5 and 9.5 is obtained, the mahogany sulfonate and the com ponents (a) and (b) forming the amine salt being in proportion to provide from 0.5 to 1.5 parts of amine salt per part of mahogany sulfonate.
- the salt of the mahogany sulfonate is a mixture of calcium mahogany sulfonate and sodium mahogany sulfonate
- the amine is monoisopropanol amine
- the aryl sulfonic acid is dodecylbenzenesulfonic acid.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
Description
i United States Patent No Drawing. Filed July 26, 1963, Ser. No. 297,974 Claims. (Cl. 252-152) This invention is concerned with novel detergent compositions. More specifically, it relates to a detergent composition adapted for incorporation into a non-polar organic dry-cleaning solvent comprising alkali metaland/ or alkaline-earth metal mahogany sulfonates and certain monoalkanolamine salts of alkyl arylsulfonic acids.
Mahogany sulfonates have ben employed to improve dry-cleaning solvents. Improved detergency and soil dispersion properties of the latter solvents have been observed. Unfortunately, such additives impart to the drycleaning solvent relatively poor water solubilizing properties. Possession of water solubilizing characteristics of detergent additives is of significant consequence, for otherwise the presence of excess water in the solventdetergent system can damage irreparably a garment to be treated. If the detergent additive could be modified so as to impart water-binding properties to an otherwise good detergent without impairing the latters effectiveness, such a product would be highly desirable.
It is an object of this invention to provide a detergent additive composition which exhibits both enhanced detersiveness and water solubilizing or water-binding properties. It is a further object of the invention to provide an improved mahogany sulfonate additive to drycleaning solvents. Other objects and advantages will become apparent from the following detailed description.
It 'has ben found that the stated objectives can be achieved readily by incorporating into a non-polar, organic drycleaning solvent a mixture of a monoalkanol amine salt of an alkylaryl sulfonic acid and either an alkali metal salt of a mahogany sulfonate or alkaline earth salt of a mahogany sulfonate having a molecular weight of at least about 425. It is surprising to find that mixtures as prepared hereinbelow specified exhibit both enhanced detergency and water binding properties.
According to the invention, neutralization of an alkylaryl sulfonic acid with an alkanol amine is performed in the presence of the alkali metal salt of an oil soluble mahogany sulfonic acid or mixtures thereof. Unexpectedly, it has been further found that the desired enhanced detergency is realized when the neutralization of the alkyl aryl sulfonic acid by means of the amine is carried out in the presence of the mahogany sulfonate.
A good practice is to incorporate about 1 part of alkali metal or alkaline earth metal mahogany sulfontae in about 0.5 part to about 1.5 part, on a weight basis, of the aforementioned amine salt, and about equal parts of each of the sulfonate and the amine salt are preferred.
In general, any commercially available oil-soluble mahogany sulfonate having an average molecular weight of at least 425 can be employed herein. It is advantageous to employ a alkalimetal salt of mahogany sulfonic acid, such as the sodium, potassium or lithium salt, although the alkaline earth metal salt, such as the calcium or baroetyl benzene sulfonic acid, nonyl benzene sulfonic acid, decyl benzene sulfonic acid, undecyl benzene sulfonic acid,
ICC
dodecyl benzene sulfonic acid, lauryl benzene sulfonic acid, tridecyl benzene sulfonic acid, myristyl benzene sulfonic acid, hexadecyl benzene sulfonic acid, octadecyl benzene sulfonic acid, l-dodecyl naphthylsulfonic acid, and fl-myristyl naphthylsulfonic acid.
Exemplary monoalkanol amines utilized in the neutralization of the alkyl aryl sulfonic acid are the following monohydroxy lower alkyl amines:
Mono-ethanol amine, Mono-n-propanol amine, Mono-isopropanol amine, Mono-n-butanol amine, Mono-isobutanol amine, and Mono-pentanol amine.
The detergent compositions, prepared by admixing the alkylaryl' sulfonic acid with the mahogany sulfonate salt and the mixture neutralized with the appropriate mono-' alkanol amine, can be incorporated into a non-polar solvent, such as Stoddards solvent, petroleum ether, deodorized kerosene, and mineral spirits.
As previously stated, it is a critically important aspect of this invention to effect neutralization of the alkyl aryl sulfonic acid with the aforementioned amine in the presence of the mahogany sulfonate salt. In general, the amine is added to a mixture of the alkyl aryl sulfonic acid and the salt of the mahogany sulfonate until a pH between 6.5 and 9.5 is obtained, and preferably between 7.0 and 8.5. At this point, an amber colored, viscous stable solution is noted. To reduce the viscosity of the resultant solution so that it can be handled with greater facility, it is a good practice to add, while preparing the solution and prior to neutralization, a small amount usually up to 25% of an inert organic solvent into the mixture. Such inert solvents are for instance:
Stoddards solvent, perchloroethylene, deodorized kerosene, mineral spirits, and mineral oil,
To further illustrate the invention, the following examples of the preferred practice are presented. These are not to be taken as limitative of the invention. Unless otherwise stated, the parts are by weight.
Example 1 To a suitable reaction vessel are admixed 44 parts of sodium mahogany sulfonate, 56 parts of mineral oil and 44 parts of dodecyl benzene sulfonic acid. To the mixture is next added 12 parts of mono-isopropanolamine. Resultant mixture obtained is found to have a pH equal to 7.5. T
Example 2 Into an appropriate reaction vessel are added 22 parts of calcium mahogany sulfonate, 56 parts of deodorized kerosene and 44 parts of dodecylbenzenesulfonic acid. The mixture is then admixed. Twelve (12) parts of monoisop-ropanol amine are then added and gently stirred. A terminal pH of 7.8 is obtained.
Example 3 T o 22 parts of sodium mahogany sulfonate, 22 parts of calcium mahogany sulfonate and 44 parts of dodecylbenzenesulfonic acid in 56 parts of petroleum ether are added while stirring 12 parts of monoisopropanol amine. The mixture is then found to possess a pH of about 8.
Example 4 A mixture of 22 parts of sodium mahogany sulfonate and 22 parts of calcium mahogany sulfonate, 40 parts TABLE I Percent Percent Percent Detergeney Redeposition Water Solvent Ex. Detergent in Stoddard Solvent Sgluble R.H.
Cotton Wool Cotton Wool Removal Oil-soluble sodium mahogany sulfonate of average MW. of about 425.." 17.8 42. 2 5. 8 10. 8 40 70 EX. 1 detergent"- 33. 56 2. 1 11.0 100 65 Ex. 2 deter ent 37 68 1. 05 6. 5 100 70 Ex. 3 deter ent 41 68 2. l 6. 5 100 65 Ex. 4 detergent. 30. 3 68 2. 1 5. 5 100 70 Monoisopropanol amine salt of dodecylbenzene sulfonic acid 27. 3 41 8. 4 19, 8 85 a of tride-cylbenzenesulfonic acid in 56 parts of petroleum ether is added to an appropriate reaction vessel. Thereafter, 9.5 parts of monoisopropanol amine are added while stirring to the mixture, whereby a pH of 7.6 is obtained.
Although in each example above monoisopropanol amine is employed, other aforementioned monoalkanolamines can be substituted to obtain similarly improved detergents.
Enhanced detersive properties of the compositions illustrated in the table below are determined in the conventional manner involving the use of a launderometer as described in the AATCC Yearbook for 1955 at page 55. In a typical run, a standard soiled swatch and stainless steel balls together with a non-polar drycleaning solvent, containing 1% by weight of the detergent additive mixture as prepared by each of the above examples are added to a lannderometer jar. After a twenty minute wash cycle, the washed swatch is removed from the jar, and dried to remove the solvent. Reflectance readings before and after washing of the soiled and unsoiled swatches are taken and recorded in percent detergency and percent redeposition, respectively. In the illustrative examples below, the initial reflectance readings of the cotton and wool swatches used are: 103 and 93, respectively. Percent detergency is determined by subtracting the reflectance reading of the soiled swatch and dividing this differonce by the difference between the initial unsoiled swatch reflectance reading and soiled reflectance reading, multiplied by 100. Thus, for instance, the percent detergency for cotton is:
where R is the reflectance reading of the soiled swatch after drycleaning. The redeposition value in percent for cotton is similarly represented by the formula:
where R is the reflectance reading of unsoiled swatches after drycleaning. In the examples below the percent detergency and percent redeposition are determined in perchloroethylene solvent.
Water binding test procedure is conducted in each of the examples tabulated below as follows:
A visual water tolerance value (V.W.T.V.) of an oil soluble detergent is a measurement of the amount of water that the detergent will hold or otherwise dissolve in solvent, such as perchloroethylene. Water tolerance value herein is obtained byvisual measurements in the formula below by adding water to a known amount of detergent dissolved in solvent until the solution shows a definite cloudiness:
V W T amt. of water (in grams) From Table I above, it can be readily seen that overall detersiveness values of the mixture is generally higher than the detersiveness values for the individual components. Advantageously, the compositions of the present invention exhibit synergistic properties with respect to sweet-stain removal.
In Table II below the visual water tolerance values are summarized.
It will be seen from the above table that the compositions of the present invention exhibit a markedly higher water binding effect than do the mahogany sulfonates. This property is related directly to the maintenance of a low or safe solvent relative humidity.
We claim:
1. A non-polar solvent compatible detergent composition consisting essentially of: i
(a) 1 part by weight of a salt of an oil-soluble mahogany sulfonate having a molecular weight of at least about 425, said salt being selected from the group consisting of alkali metal, alkaline earth metal and mixtures thereof, and
(b) from 0.5 part to 1.5 parts of monohydroxy lower alkyl amine salt of a higher alkyl aryl sulfonic acid, said amine salt being formed by reacting said monohydroxy lower alkyl amine with said higher alkyl aryl sulfonic acid in the presence of said mahogany sulfonate, and said mixture being substantially neutralized to a pH of from about 6.5 to 9.5.
2. A non-polar solvent compatible detergent composition consisting essentially of:
(a) 1 part of a salt of an oil-soluble mahogany sulfonate having a molecular Weight of at least about 425, said salt being selected from the group consisting of alkali metal, alkaline earth metal and mixtures thereof, and
(b) 1 part of monohydroxy lower alkyl amine salt of a higher alkyl aryl sulfonic acid, said amine salt being formed by reacting said monohydroxy lower alkyl amine with said higher alkyl aryl sulfonic acid in the presence of said mahogany sulfonate, and said mixture being substantially neutralized to a pH of from about 6.5 to 9.5.
3. The detergent composition according to claim 1 in which the mahogany sulfonate is the sodium salt and the monoalkanol amine salt is monoisopropanol amine. salt of dodecylbenzenesulfonic acid.
4. The detergent composition according to claim 1 in which the mahogany sulfonate is the sodium salt and the;
monoisopropanol amine salt monoalkanol amine salt is of tride-cylbenzenesulfonic acid.
5'. The detergent composition according to claim 1 in which the sulfonate is a mixture of calcium mahogany sulfonate and sodium mahogany sulfonate and the monoalkanol amine salt is monoisopropanol amine salt of dodecylbenzenesulfonic acid.
6. A process for preparing an oil-soluble, detergent composition which consists essentially in the steps of: admixing in the presence of a salt of an oil-soluble mahogany sulfonate having an average molecular weight of at least 425, said salt being selected from the group consisting of alkali metal, alkaline earth metal and mixtures thereof, (a) a higher alkyl aryl sulfonic acid and (b) monohydroxy lower alkyl until a pH between about 6.5 and 9.5 is obtained, the mahogany sulfonate and the com ponents (a) and (b) forming the amine salt being in proportion to provide from 0.5 to 1.5 parts of amine salt per part of mahogany sulfonate.
7. The process according to claim 6 in which the salt of the mahogany sulfonate is sodium mahogany sulfonate, the monoalkanol amine is monoisopropanol amine and the aryl sulfonic acid is dodecylbenzenesulfonic acid.
8. The process according to claim 6 in which the salt of the mahogany sulfonate is a mixture of calcium mahogany sulfonate and sodium mahogany sulfonate, the amine is monoisopropanol amine, and the aryl sulfonic acid is dodecylbenzenesulfonic acid.
9. The process according to claim 6 in which the salt of the mahogany sulfonate is sodium mahogany sulfonate, the amine is monoisopropanol amine, and the aryl sulfonic acid is tridecylbenzenesulfonic acid.
10. The process according to claim 6 in which the salt of the mahogany sulfonate is potassium mahogany sulfonate, the amine is monoisopropanol amine, and the aryl sulfonic acid is myristylbenzenesulfonic acid.
References Cited by the Examiner UNITED STATES PATENTS 2,271,635 2/1942 Flett 252-161 2,566,298 9/1951 Irwin 252-153 X 3,012,969 12/1961 Minne et al. 252153 3,091,508 5/1963 Edwards 25289 3,101,240 8/1963 Mathews 8-142 3,163,493 12/1964 Hess 8142 3,174,935 3/1965 Eccles et al 252-161 LEON D. ROSDOL, Primary Examiner.
SAMUEL H. BIECH, S. E. DARDEN,
Assistant Examiners.
Claims (1)
1. A NON-POLAR SOLVENT COMPATIBLE DETERGENT COMPOSITION CONSISTING ESSENTIALLY OF: (A) 1 PART BY WEIGHT OF A SALT OF AN OIL-SOLUBLE MAHOGANY SULFONATE HAVING A MOLECULAR WEIGHT OF AT LEAST ABOUT 425, SAID SALT BEING SELECTED FROM THE GROUP CONSISTING OF ALKALI METAL, ALKALINE EARTH METAL AND MIXTURES THEREOF, AND (B) FROM 0.5 PART TO 1.5 PARTS OF MONOHYDROXY LOWER ALKYL AMINE SALT OF A HIGHER ALKYL ARYL SULFONIC ACID, SAID AMINE SALT BEING FORMED BY REACTING SAID MONOHYDROXY LOWER ALKYL AMINE WITH SAID HIGHER ALKYL ARYL SULFONIC ACID IN THE PRESENCE OF SAID MAHOGANY SULFONATE, AND SAID MIXTURE BEING SUBSTANTIALLY NEUTRALIZED TO A PH OF FROM ABOUT 6.5 TO 9.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US297974A US3310499A (en) | 1963-07-26 | 1963-07-26 | Novel detergent compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US297974A US3310499A (en) | 1963-07-26 | 1963-07-26 | Novel detergent compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3310499A true US3310499A (en) | 1967-03-21 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US297974A Expired - Lifetime US3310499A (en) | 1963-07-26 | 1963-07-26 | Novel detergent compositions |
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| US (1) | US3310499A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3538006A (en) * | 1966-07-27 | 1970-11-03 | Witco Chemical Corp | Emulsion cleaner |
| US3655572A (en) * | 1970-01-21 | 1972-04-11 | Chevron Res | Water-containing dry cleaning compositions |
| US3714075A (en) * | 1969-10-07 | 1973-01-30 | Ici Ltd | Chlorinated hydrocarbon compositions and uses thereof |
| US4102824A (en) * | 1976-06-25 | 1978-07-25 | Kao Soap Co., Ltd. | Non-aqueous detergent composition |
| JPS5449987A (en) * | 1977-09-28 | 1979-04-19 | Zenji Mori | Manufacture of liquid surfactant composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2271635A (en) * | 1935-09-25 | 1942-02-03 | Allied Chem & Dye Corp | Dry cleaning composition and method |
| US2566298A (en) * | 1951-09-04 | Cleaning composition | ||
| US3012969A (en) * | 1952-12-30 | 1961-12-12 | Shell Oil Co | Volatile organic liquids of increased electrical conductivity |
| US3091508A (en) * | 1959-07-27 | 1963-05-28 | Le Roy B Edwards | Dry cleaning composition and method of use |
| US3101240A (en) * | 1953-06-29 | 1963-08-20 | Martin B Mathews | Dry cleaning |
| US3163493A (en) * | 1960-12-23 | 1964-12-29 | Stockhausen & Cie Chem Fab | Process for disinfecting dry cleaning in conventional solvents |
| US3174935A (en) * | 1961-06-20 | 1965-03-23 | Monsanto Co | Alkylbenzene sulfonate slurry |
-
1963
- 1963-07-26 US US297974A patent/US3310499A/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2566298A (en) * | 1951-09-04 | Cleaning composition | ||
| US2271635A (en) * | 1935-09-25 | 1942-02-03 | Allied Chem & Dye Corp | Dry cleaning composition and method |
| US3012969A (en) * | 1952-12-30 | 1961-12-12 | Shell Oil Co | Volatile organic liquids of increased electrical conductivity |
| US3101240A (en) * | 1953-06-29 | 1963-08-20 | Martin B Mathews | Dry cleaning |
| US3091508A (en) * | 1959-07-27 | 1963-05-28 | Le Roy B Edwards | Dry cleaning composition and method of use |
| US3163493A (en) * | 1960-12-23 | 1964-12-29 | Stockhausen & Cie Chem Fab | Process for disinfecting dry cleaning in conventional solvents |
| US3174935A (en) * | 1961-06-20 | 1965-03-23 | Monsanto Co | Alkylbenzene sulfonate slurry |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3538006A (en) * | 1966-07-27 | 1970-11-03 | Witco Chemical Corp | Emulsion cleaner |
| US3714075A (en) * | 1969-10-07 | 1973-01-30 | Ici Ltd | Chlorinated hydrocarbon compositions and uses thereof |
| US3655572A (en) * | 1970-01-21 | 1972-04-11 | Chevron Res | Water-containing dry cleaning compositions |
| US4102824A (en) * | 1976-06-25 | 1978-07-25 | Kao Soap Co., Ltd. | Non-aqueous detergent composition |
| JPS5449987A (en) * | 1977-09-28 | 1979-04-19 | Zenji Mori | Manufacture of liquid surfactant composition |
| JPS6033879B2 (en) * | 1977-09-28 | 1985-08-05 | 善次 森 | Method for producing liquid surfactant composition |
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