US2383526A - Detergent composition - Google Patents
Detergent composition Download PDFInfo
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- US2383526A US2383526A US449495A US44949542A US2383526A US 2383526 A US2383526 A US 2383526A US 449495 A US449495 A US 449495A US 44949542 A US44949542 A US 44949542A US 2383526 A US2383526 A US 2383526A
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- Prior art keywords
- detergent
- nitrile
- water
- acids
- cleansing
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Classifications
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- 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
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
Definitions
- This invention relates to washing and cleansing compositions of improved efficiency containing as the essential detergent material an organic sulfuric acid derivative containing a sulfa 'e or sulfonate group.
- t is an object of my invention to provide orgaiiic sulfate and sulfonate detergent compositions having improved detergent properties.
- a further object of my invention is to provide an enhancing agent for organic sulfate and sulfonate detergents.
- nitriles which come within the scope of this invention and which may be employed in the practice thereof are capric nitrile, lauric nitrile, myristic nitrile, and mixtures of nitriles of fatty acid mixtures consisting predominantly of fatty acids having ten to fourteen carbon atoms, such as those fatty acid mixtures obtainable from oils of the coconut 011 type, of which coconut oil and palm kernel oil are well known examples.
- the invention is applicable to the improvement of ,all detergents coming within the class above In tioned.
- the advantage of the invention is th improvement in the cleansing power of those sulfates and sulfonates alreadycharacterized by substantial power to cleanse rather than the conferring of cleansing power on those materials, such as wetting and softening agents, which are inactive as detergents.
- detergent compounds with which the above nitriles may be used with advantage are the water-soluble salts of the higher molecular weight alkyl sulfuric acids which have distinct and pronounced detergent power, making the product suitable for use in cleansing and laundering operations.
- the invention is particularly applicable to the improvement of the already known detergents in which the principal active constituent is a watersoluble salt of lauryl or oleyl sulfuric acid, for example, triethanolammonium alkyl sulfate from the mixed higher alcohols obtainable by These compounds are the nitriles of fatty reducing coconut oil or the sodium alkyl sulfate derived from the higher alcohols of sperm oil, but the invention'does not afford a means of making a practical detergent out of a compound initially lacking detergent properties, such as sodium butyl sulfate, triisopropyl-naphthalene sulfonate, Turkey red oil, or dioctyl ester of sodium sulfosuccinate.
- water-soluble salts of other alkyl sulfuric acids having decided detergent value and having eight to eighteen carbon atoms in the alkyl radical are improved by the addition of the nitriles herein covered, and especially are these nitriles useful in improving the detergent power of the salts of those alkyl sulfuric acids derived from a mixture of higher alcohols obtained from oils of the coconut oil type, such as coconut oil, palm kernel oil, etc.
- alkyl sulfate detergents Besides the alkyl sulfate detergents referred to above, other compounds having a sulfuric acid ester group and possessing value as washing and detergent agents in aqueous solution are improved by the addition of the nitriles herein covered. For example, highly beneficial results will.
- nitriles are employed with compounds such as the water-soluble salts of sulfuric acid esters of higher fatty acid monoglycerides (sodium salt of the coconut oil fatty ester of 1,2-dihydroxy propane 3 sulfuric acid ester) and of the sulfated higher fatty acid alkylolamides (sodium salt of sulfated coconut oil fatty acid ethanolamide).
- the improving agents of this invention may also be employed with compounds having a true sulfonate group, that is, compounds possessing a substantial power to wash and cleanse in aqueous solution in the absence of an enhancing agent.
- compounds having a true sulfonate group that is, compounds possessing a substantial power to wash and cleanse in aqueous solution in the absence of an enhancing agent.
- beneficial results will be noted when the nitriles are employed with water-soluble salts of higher mono fatty acid esters of 1,2-dihydroxy propane 3 sulfonic acid, the sodium salt of the coconut oil fatty acid ester being an excellent example of this type of detergent.
- nitriles are employed'with such detergents as the watersoluble salts of the higher fatty acid monoesters of lower molecular weight hydroxy alkyl sulfonic acids (oleic acid ester of the sodium salt of isethionic acid) and of the higher fatty acid amides of lower molecular amino alkyl sulfonic acids (ammonium salt of oleic acid amide of N-methyl taurine).
- nitriles may be employed with water-soluble salts of thehigher alcohol esters of sulfocarboxyllc acids (sodium salt of the lauryl alcohol ester of sulfoacetic acid), higher alkylated benzene sulfonic acids (potassium salt of the sulfonic acid derived from the condensation product of benzene and a chlorinated kerosene fraction containing predominantly twelve carbon atoms per molecule), and ethers of high molecular alcohols and. lower hydroxy sulfonic acids (monolauryl ether of 1,2-dihydroxy propane 3 sodium sulionate).
- sulfocarboxyllc acids sodium salt of the lauryl alcohol ester of sulfoacetic acid
- higher alkylated benzene sulfonic acids potassium salt of the sulfonic acid derived from the condensation product of benzene and a chlorinated kerosene fraction containing predominantly twelve carbon
- nitrile usage will vary depending on the specific combination of ingredients, but in general the quantity of nitrile will be less than the quantity of active detergent ingredient. I prefer to employ from about ten per cent to about twenty-five per cent of nitrile based on the active detergent, but marked improvement can be obtained with smaller proportions and larger proportions, for example proportions within the range of about five per cent to about forty, per cent. I
- Example 1 To 8 parts of capric nitrile are added 92 parts of commercial sodium alkyl sulfate (40.0% active ingredient) prepared from the higher alcohols obtained by the hydrogenation of coconut oil. This mixture will contain the capric nitrile and the active alkyl sulfate in the ratio of 124.6 and may be employed as a detergent in washing operations with highly satisfactory results as to detergent efilciency, superior to those obtained by the use of the alkyl sulfate alone.
- commercial sodium alkyl sulfate 40.0% active ingredient
- Example 2 An improved detergent is prepared by mixing 94 parts of a commercial sodium alkyl sulfate prepared from the higher alcohols obtained by the reduction of coconut oil and containing 40% active ingredient, with 6. parts of lauric nitrile. The detergent so prepared is much superior to the commercial detergent alone in cleansing operations.
- Example 3 A detergent of superior washing power is prepared by mixing 92 parts of a commercial sodium alkyl sulfate detergent containing 40% active ingredient with 8 parts of myristic nitrile.
- Example 4 An improved detergent is prepared by mixing 95 parts of Igepon T containing 38% sodium salt of oleic acid amide of N-methyl taurine as active ingredient, with parts of lauric nitrile.
- Example 5 To 95 parts of a commercial detergent containing 38% of the sodium salt of the ester of sulfoacetic acid and the mixture of higher alcohols obtained from coconut oil by reduction are added 5 parts of lauric nitrile. The resulting mixture has detergent power superior to the sulfoacetic acid ester without nitrile.
- Example 6 An improved detergent is prepared by mixing 95 parts of a detergent containing as active constituent 38 of the coconut oil fatty acid monoester oi' 1,2-dihydroxy propane 3 sodium sulfonate, with 5 parts of lauric nitrile.
- Example 7 A detergent of superior washing power, especially on wool, is prepared by mixing 95 parts of a commercial detergent containing as oester of 1,2-dihydroxy propane 3 sodium sulfate, with 5 parts of lauric nitrile.
- My invention is not limited to any particular method of mixing the nitriles with the sulfate or sulfonate detergents. They may be incorporated in the detergent mixture in any of the forms in which the detergents are manufactured.
- the nitrile may be mechanically mixed in, it may be crutched into the detergent in the form of a slurry, and it may be dissolved in a solution of the detergent. While such ready-for-use mixtures may be manufactured and may be preferable for many purposes, it is likewise within the scope of my invention to 'add the nitriles to the water prior to the adding of the detergent, or vice versa, or to add both nitrile and detergent simultaneously but separately to the water.
- a cleansing and laundering composition comprising essentially a mixture of a detergent having pronounced detergent power and selected from'the group consisting of water-soluble salts.
- a cleansing and' laundering composition comprising essentially a mixture of a detergent having pronounced detergent power and selected from the group consisting of water-soluble salts of higher alkyl sulfuric acids, higher fatty acid esters of lower molecular weight hydroxy allgvi sulfonic acids, higher fatty acid amides of low molecular amino alkyl sulfonic acids, higher fatty acid monoglyceride sulfuric acids, higher alcohol esters of sulfocarboxylic acids, higher alkylated benzene sulfonie acids, higher alkyl ethers of low molecular hydroxy alkyl sulfonic acids, and higher fatty acid alkylolamide sulfuric acids, and a nitrile of a fatty acid having 10 to 14 carbon atoms, the amount by weight of the nitrile being less than the amount by weight of the detergent but sufficient to enhance the detergent power thereof.
- composition claimed in claim 1 in which the nitrile is lauric nitrile.
- composition claimed in claim 1 in which the nitrile is capric nitrile.
- nitrile is myrstic nitrile.
- the cleansing composition claimedin claim 1 in which the amount of the fatty acid nitrile is from about per cent to about 25 per cent by weight of the detergent.
- a cleansing composition comprising essentially a mixture of a water-soluble salt of an alkyl sulfuric acid having 8 to 18 carbon atoms in the alkyl radical, the said salt having pronounced detergent power, and'a nitrile of a fatty acid having 10 to 14 carbon atoms, the amount byv weight of the nitrile being less than the amount by weight of the said water-soluble salt but sufficient to enhance the detergent power thereof.
- a cleansing composition comprising essentially a mixture of a water-soluble salt of alkyl sulfurimacids having 8 to 18 carbon atoms in the alkyl radical and having pronounced detergent properties,'with a mixture of nitriles derived from a mixture of fatty acids obtained from an oil of the coconut oil group and having 10 to 14 carbon atoms, the amount by weight of the nitrile mixture beingless than the amount by weight of the water-soluble salt but sufiicientto enhance I the detergent power thereof.
- a cleansing composition comprising essen tially a mixture 'of a water-soluble salt of alk'yl sulfuric acids derived from higher'alcohols obtained by reduction of coconut oil, the said salt having pronounced detergent power, and a mixture .of nitriles derived from the fatty acids of coconut oil and having predominantly 10 to 14 ture of alkyl sulfuric acids consisting predominantly of laurylsulfurlc acid, the said salt having' pronounced detergent power, and lauric nitrile, the amount by weight of the nitrile being less than the amount by weight of the water-soluble salt but sufiicient. to enhance the detergent nounced detergent power, and lauric nitrile, the
- a cleansing composition comprising essentially a mixture of a water-soluble salt of the 17.
- a cleansing composition comprising essentially a mixture of a water-soluble salt of coconut oil monoglyceride sulfuric acid, the said salt havingpronounced detergent power, and a nitrile of a fatty acid having 10 to 14 carbon atoms in the molecule, the amount by weight of the nitrile being less than the amount by weight of the water-soluble salt but sufilcient to enhance the detergent power thereof.
Description
Patented Aug. 28, 1945 Nathaniel Beverley Tucker, Louisville, Ky.,
signor to The Procter & Gamble Company, Cincinnati, Ohio, a corporation of Ohio No Drawing. Application July 2, 1942, Serial No. 449,495
17 Claims.
This invention relates to washing and cleansing compositions of improved efficiency containing as the essential detergent material an organic sulfuric acid derivative containing a sulfa 'e or sulfonate group.
t is an object of my invention to provide orgaiiic sulfate and sulfonate detergent compositions having improved detergent properties.
A further object of my invention is to provide an enhancing agent for organic sulfate and sulfonate detergents.
Other objects will be apparent from the following description.
I have found that certain compounds closely related to each other are effective for increasing the cleansing action of sulfate and'sulfonate detergents, especially in the washing of woolen fabncs. acids having ten to fourteen carbon atoms in the molecule. By themselves these nitriles are not laundering agents, but when added to a detergent of the class above named they markedly enhance the cleansing effect thereof.
Specific examples of nitriles which come within the scope of this invention and which may be employed in the practice thereof are capric nitrile, lauric nitrile, myristic nitrile, and mixtures of nitriles of fatty acid mixtures consisting predominantly of fatty acids having ten to fourteen carbon atoms, such as those fatty acid mixtures obtainable from oils of the coconut 011 type, of which coconut oil and palm kernel oil are well known examples.
The invention is applicable to the improvement of ,all detergents coming within the class above In tioned. The advantage of the invention is th improvement in the cleansing power of those sulfates and sulfonates alreadycharacterized by substantial power to cleanse rather than the conferring of cleansing power on those materials, such as wetting and softening agents, which are inactive as detergents.
outstandingly interesting detergent compounds with which the above nitriles may be used with advantage are the water-soluble salts of the higher molecular weight alkyl sulfuric acids which have distinct and pronounced detergent power, making the product suitable for use in cleansing and laundering operations. Thus the invention is particularly applicable to the improvement of the already known detergents in which the principal active constituent is a watersoluble salt of lauryl or oleyl sulfuric acid, for example, triethanolammonium alkyl sulfate from the mixed higher alcohols obtainable by These compounds are the nitriles of fatty reducing coconut oil or the sodium alkyl sulfate derived from the higher alcohols of sperm oil, but the invention'does not afford a means of making a practical detergent out of a compound initially lacking detergent properties, such as sodium butyl sulfate, triisopropyl-naphthalene sulfonate, Turkey red oil, or dioctyl ester of sodium sulfosuccinate.
In addition to the alkyl sulfate detergents specifically mentioned above, water-soluble salts of other alkyl sulfuric acids having decided detergent value and having eight to eighteen carbon atoms in the alkyl radical are improved by the addition of the nitriles herein covered, and especially are these nitriles useful in improving the detergent power of the salts of those alkyl sulfuric acids derived from a mixture of higher alcohols obtained from oils of the coconut oil type, such as coconut oil, palm kernel oil, etc.
Besides the alkyl sulfate detergents referred to above, other compounds having a sulfuric acid ester group and possessing value as washing and detergent agents in aqueous solution are improved by the addition of the nitriles herein covered. For example, highly beneficial results will.
be noted when the nitriles are employed with compounds such as the water-soluble salts of sulfuric acid esters of higher fatty acid monoglycerides (sodium salt of the coconut oil fatty ester of 1,2-dihydroxy propane 3 sulfuric acid ester) and of the sulfated higher fatty acid alkylolamides (sodium salt of sulfated coconut oil fatty acid ethanolamide).
The improving agents of this invention may also be employed with compounds having a true sulfonate group, that is, compounds possessing a substantial power to wash and cleanse in aqueous solution in the absence of an enhancing agent. For example, beneficial results will be noted when the nitriles are employed with water-soluble salts of higher mono fatty acid esters of 1,2-dihydroxy propane 3 sulfonic acid, the sodium salt of the coconut oil fatty acid ester being an excellent example of this type of detergent. Beneficial results will be noted also when the nitriles are employed'with such detergents as the watersoluble salts of the higher fatty acid monoesters of lower molecular weight hydroxy alkyl sulfonic acids (oleic acid ester of the sodium salt of isethionic acid) and of the higher fatty acid amides of lower molecular amino alkyl sulfonic acids (ammonium salt of oleic acid amide of N-methyl taurine). Likewise the nitriles may be employed with water-soluble salts of thehigher alcohol esters of sulfocarboxyllc acids (sodium salt of the lauryl alcohol ester of sulfoacetic acid), higher alkylated benzene sulfonic acids (potassium salt of the sulfonic acid derived from the condensation product of benzene and a chlorinated kerosene fraction containing predominantly twelve carbon atoms per molecule), and ethers of high molecular alcohols and. lower hydroxy sulfonic acids (monolauryl ether of 1,2-dihydroxy propane 3 sodium sulionate).
The above examples are merely specific illustrations of the numerous detergents which can be rendered more eflicient in cleansing and laundering operations when used in conjunction with nitriles in accordance with my invention, and I do not wish to be limited thereto.
In the practice of my invention the nitrile usage will vary depending on the specific combination of ingredients, but in general the quantity of nitrile will be less than the quantity of active detergent ingredient. I prefer to employ from about ten per cent to about twenty-five per cent of nitrile based on the active detergent, but marked improvement can be obtained with smaller proportions and larger proportions, for example proportions within the range of about five per cent to about forty, per cent. I
The invention will be more clearly understood from the following examples, but these examples are merely illustrative of the manner in which my invention may be practiced and are not to be construed as limiting. All parts are by weight.
Example 1.To 8 parts of capric nitrile are added 92 parts of commercial sodium alkyl sulfate (40.0% active ingredient) prepared from the higher alcohols obtained by the hydrogenation of coconut oil. This mixture will contain the capric nitrile and the active alkyl sulfate in the ratio of 124.6 and may be employed as a detergent in washing operations with highly satisfactory results as to detergent efilciency, superior to those obtained by the use of the alkyl sulfate alone.
Example 2.-An improved detergent is prepared by mixing 94 parts of a commercial sodium alkyl sulfate prepared from the higher alcohols obtained by the reduction of coconut oil and containing 40% active ingredient, with 6. parts of lauric nitrile. The detergent so prepared is much superior to the commercial detergent alone in cleansing operations.
Example 3.A detergent of superior washing power is prepared by mixing 92 parts of a commercial sodium alkyl sulfate detergent containing 40% active ingredient with 8 parts of myristic nitrile.
Example 4.--An improved detergent is prepared by mixing 95 parts of Igepon T containing 38% sodium salt of oleic acid amide of N-methyl taurine as active ingredient, with parts of lauric nitrile.
Example 5.To 95 parts of a commercial detergent containing 38% of the sodium salt of the ester of sulfoacetic acid and the mixture of higher alcohols obtained from coconut oil by reduction are added 5 parts of lauric nitrile. The resulting mixture has detergent power superior to the sulfoacetic acid ester without nitrile.
Example 6.-An improved detergent is prepared by mixing 95 parts of a detergent containing as active constituent 38 of the coconut oil fatty acid monoester oi' 1,2-dihydroxy propane 3 sodium sulfonate, with 5 parts of lauric nitrile.
Example 7.--A detergent of superior washing power, especially on wool, is prepared by mixing 95 parts of a commercial detergent containing as oester of 1,2-dihydroxy propane 3 sodium sulfate, with 5 parts of lauric nitrile.
I have repeatedly referred to the superior washing powder of detergents prepared in accordance with my invention and I wish to emphasize here that this superiority is apparent to the user and represents a source of substantial saving in detergent usage. For example, detergents such as those of the above sbeciflec examples, that is, commercial detergent in admixture with nitrile, when employed in 0.2 per cent concentration in hard water, a normal concentration used in laundering, will wash much whiter than any concentration of the commercial detergent without added nitrile. In general, a solution of a cleansing compound prepared in accordance with my invention will wash as white as or whiter than a solution containing a much larger concentration of detergent without added nitrile.
My invention is not limited to any particular method of mixing the nitriles with the sulfate or sulfonate detergents. They may be incorporated in the detergent mixture in any of the forms in which the detergents are manufactured. The nitrile may be mechanically mixed in, it may be crutched into the detergent in the form of a slurry, and it may be dissolved in a solution of the detergent. While such ready-for-use mixtures may be manufactured and may be preferable for many purposes, it is likewise within the scope of my invention to 'add the nitriles to the water prior to the adding of the detergent, or vice versa, or to add both nitrile and detergent simultaneously but separately to the water.
Having thus described my invention, what I claim and desire to secure by Letters Patent is:
1. A cleansing and laundering composition comprising essentially a mixture of a detergent having pronounced detergent power and selected from'the group consisting of water-soluble salts.
of organic sulfonic acids and water-soluble salts of aliphatic sulfuric acid esters, and a nitrile of a fatty acid, having 10 to 14 carbon atoms, the amount by weight of the nitrile being less than the amount by weight of the detergent but sufficient to enhance the detergent power thereof.
2. A cleansing and' laundering composition comprising essentially a mixture of a detergent having pronounced detergent power and selected from the group consisting of water-soluble salts of higher alkyl sulfuric acids, higher fatty acid esters of lower molecular weight hydroxy allgvi sulfonic acids, higher fatty acid amides of low molecular amino alkyl sulfonic acids, higher fatty acid monoglyceride sulfuric acids, higher alcohol esters of sulfocarboxylic acids, higher alkylated benzene sulfonie acids, higher alkyl ethers of low molecular hydroxy alkyl sulfonic acids, and higher fatty acid alkylolamide sulfuric acids, and a nitrile of a fatty acid having 10 to 14 carbon atoms, the amount by weight of the nitrile being less than the amount by weight of the detergent but sufficient to enhance the detergent power thereof.
3. A cleansing and laundering composition claimed in claim 1, in which the nitrile is derived from a mixture of fatty acids consisting predominantly of fatty acids of 10 to 14 carbon atoms.
4. A cleansing and laundering composition claimed in claim 1, in which the nitrile is derived from a mixture of fatty acids obtained from an oil of the coconut oil group and consisting predominantly of fatty acids having 10 to 14 carbon atoms.
5. The composition claimed in claim 1, in which the nitrile is lauric nitrile.
6. The composition claimed in claim 1, in which the nitrile is capric nitrile.
7. The composition claimed in claim 1, in
which the nitrile is myrstic nitrile.
8. A cleansing composition claimed in claim 1, in which the amount of the fatty acid nitrile is from about per cent to about 40 per cent by weight of the detergent.
9. The cleansing composition claimedin claim 1 in which the amount of the fatty acid nitrile is from about per cent to about 25 per cent by weight of the detergent.
10. A cleansing composition comprising essentially a mixture of a water-soluble salt of an alkyl sulfuric acid having 8 to 18 carbon atoms in the alkyl radical, the said salt having pronounced detergent power, and'a nitrile of a fatty acid having 10 to 14 carbon atoms, the amount byv weight of the nitrile being less than the amount by weight of the said water-soluble salt but sufficient to enhance the detergent power thereof.
11. A cleansing composition comprising essentially a mixture of a water-soluble salt of alkyl sulfurimacids having 8 to 18 carbon atoms in the alkyl radical and having pronounced detergent properties,'with a mixture of nitriles derived from a mixture of fatty acids obtained from an oil of the coconut oil group and having 10 to 14 carbon atoms, the amount by weight of the nitrile mixture beingless than the amount by weight of the water-soluble salt but sufiicientto enhance I the detergent power thereof.
12. A cleansing composition comprising essen tially a mixture 'of a water-soluble salt of alk'yl sulfuric acids derived from higher'alcohols obtained by reduction of coconut oil, the said salt having pronounced detergent power, and a mixture .of nitriles derived from the fatty acids of coconut oil and having predominantly 10 to 14 ture of alkyl sulfuric acids consisting predominantly of laurylsulfurlc acid, the said salt having' pronounced detergent power, and lauric nitrile, the amount by weight of the nitrile being less than the amount by weight of the water-soluble salt but sufiicient. to enhance the detergent nounced detergent power, and lauric nitrile, the
being less than the amount by weight of the water-soluble salt but suflicient to enhance the detergent-power thereof.
16. A cleansing composition comprising essentially a mixture of a water-soluble salt of the 17. A cleansing composition comprising essentially a mixture of a water-soluble salt of coconut oil monoglyceride sulfuric acid, the said salt havingpronounced detergent power, and a nitrile of a fatty acid having 10 to 14 carbon atoms in the molecule, the amount by weight of the nitrile being less than the amount by weight of the water-soluble salt but sufilcient to enhance the detergent power thereof.
NATHANIEL BEVERLEY TUCKER.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US449495A US2383526A (en) | 1942-07-02 | 1942-07-02 | Detergent composition |
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US449495A US2383526A (en) | 1942-07-02 | 1942-07-02 | Detergent composition |
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US2383526A true US2383526A (en) | 1945-08-28 |
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US449495A Expired - Lifetime US2383526A (en) | 1942-07-02 | 1942-07-02 | Detergent composition |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4491525A (en) * | 1980-09-12 | 1985-01-01 | Phillips Petroleum Company | Oil recovery with surfactant flooding |
-
1942
- 1942-07-02 US US449495A patent/US2383526A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4491525A (en) * | 1980-09-12 | 1985-01-01 | Phillips Petroleum Company | Oil recovery with surfactant flooding |
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