US3310498A - Novel detergent compositions - Google Patents
Novel detergent compositions Download PDFInfo
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- US3310498A US3310498A US297953A US29795363A US3310498A US 3310498 A US3310498 A US 3310498A US 297953 A US297953 A US 297953A US 29795363 A US29795363 A US 29795363A US 3310498 A US3310498 A US 3310498A
- Authority
- US
- United States
- Prior art keywords
- sulfonic acid
- amine
- mahogany sulfonate
- alkyl aryl
- salt
- 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 description 30
- 239000003599 detergent Substances 0.000 title description 17
- -1 AMINE SALT Chemical class 0.000 claims description 39
- 241000158728 Meliaceae Species 0.000 claims description 30
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 20
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- 238000005108 dry cleaning Methods 0.000 description 6
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 5
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- 229960004418 trolamine Drugs 0.000 description 3
- 230000000007 visual effect Effects 0.000 description 3
- PVXSFEGIHWMAOD-UHFFFAOYSA-N 2-tridecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O PVXSFEGIHWMAOD-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 229940043237 diethanolamine Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- BFIAIMMAHAIVFT-UHFFFAOYSA-N 1-[bis(2-hydroxybutyl)amino]butan-2-ol Chemical compound CCC(O)CN(CC(O)CC)CC(O)CC BFIAIMMAHAIVFT-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical group CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- UAZLASMTBCLJKO-UHFFFAOYSA-N 2-decylbenzenesulfonic acid Chemical compound CCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O UAZLASMTBCLJKO-UHFFFAOYSA-N 0.000 description 1
- CTIFKKWVNGEOBU-UHFFFAOYSA-N 2-hexadecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O CTIFKKWVNGEOBU-UHFFFAOYSA-N 0.000 description 1
- AQQPJNOXVZFTGE-UHFFFAOYSA-N 2-octadecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O AQQPJNOXVZFTGE-UHFFFAOYSA-N 0.000 description 1
- QWHHBVWZZLQUIH-UHFFFAOYSA-N 2-octylbenzenesulfonic acid Chemical compound CCCCCCCCC1=CC=CC=C1S(O)(=O)=O QWHHBVWZZLQUIH-UHFFFAOYSA-N 0.000 description 1
- WPTFZDRBJGXAMT-UHFFFAOYSA-N 4-nonylbenzenesulfonic acid Chemical compound CCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 WPTFZDRBJGXAMT-UHFFFAOYSA-N 0.000 description 1
- UCDCOJNNUVYFKJ-UHFFFAOYSA-N 4-undecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 UCDCOJNNUVYFKJ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
-
- 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
- neutralization of an alkyl aryl sulfonic acid with an alkanol amine is performed in the presence of the alkali metal salt of an oil-soluble mahogany sulfonic acid or alkaline earth' metal of an oil-soluble mahogany sulfonic acid.
- the desired result cannot be realized where the neutraliza tion of an alkyl aryl sulfonic acid is performed in the absence of a mahogany sulfonate prior to admixture with the latter.
- 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.
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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
3,310,498 NOVEL DETERGENT COMPOSITIONS Edwin E. Michaels, Stamford, and Clayton A. Wetmore,
Norwa'ik, Conn., assignors to Stamford Chemical Industries, Inn, Cincinnati, Ohio, a corporation of Ohio No Drawing. Filed duly 26, 1953, Ser. No. 297,953 6 Claims. (Cl. 252-152) The present invention relates to novel detergent compositions. More particularly, it relates to a detergent composition adapted for incorporation into a highly polar organic drycleaning solvent comprising alkali metal mahogany sulfonates and certain alkanol amine salts of alkyl aryl sulfonic acids.
In the prior practice, mahogany sulfonates have been employed to improve drycleaning solvents, such as Stoddard solvent orperchloroethylene. Improved detergency v and soil dispersion properties of the latter solvents have 'latters eflectiveness, 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 detailed description following.
It has been found that the objects stated above can be achieved by incorporating into a polar organic drycleaning solvent a mixture of a polyalkanol amine salt of an alkyl aryl sulfonic acid and an alkali metal or alkaline earth metal salt of a mahogany sulfonate having a molecular weight above about 425. Surprisingly, mixtures prepared as hereinbelow specified, exhibit both enhanced detergency and water-binding properties.
According to the invention, neutralization of an alkyl aryl sulfonic acid with an alkanol amine is performed in the presence of the alkali metal salt of an oil-soluble mahogany sulfonic acid or alkaline earth' metal of an oil-soluble mahogany sulfonic acid. Surprisingly, the desired result cannot be realized where the neutraliza tion of an alkyl aryl sulfonic acid is performed in the absence of a mahogany sulfonate prior to admixture with the latter. It has been further found that from one part of the alkali metal-or alkaline earth metal mahogany sulfonate to from about one-half to about one-and one half on a weight basis, of the amine salt, and preferably an equal weight mixture of each, is suflicient as a good operating practice.
In general, any commercially available oil-soluble mahogany sulfona'te having an average molecular weight of at least 425 can be employed herein. It is advantageous to employ the alkali metal salt of mahogany sulfonic acid, such as the sodium, potassium or lithuim salt thereof, although the alkaline earth metal salts, such as calcium or barium, may also be so used.
- The higher alkyl aryl sulfonic acid to be amine neutralized can be widely varied. Illustrative acids are:
octyl benzene sulfonic acid, nonyl benzene sulfonic acid, decyl benzene sulfonic acid, undecyl benzene sulfonic acid,
United States Patent dodecyl benzene sulfonic acid,
1 lauryl benzene sulfonic acid,
tridecyl benzene sulfonic acid, myristyl "benzene sulfonic acid, hexadecyl benzene sulfonic acid, octadecyl benzene sulfonic acid, ,B-dodecyl naphthyl sulfonic acid, and ,B-myristyl naphthyl sulfonic acid.
In' general, the alkyl substi'tuent contains from 8 to 18 carbon atoms.
The polyalkanol amines utilized in the neutralization of the alkyl aryl sulfonic acid are illustratively:
diethanol amine, triethanol amine, di-n-propanol amine, di-isopropanol amine, and tributanol amine.
Significantly, monoalkanol amines alone cannot be employed herein since they are substantially incompatible with the polar organic solvent herein employed. These solvents are, for instance, perchloroethylene, trichloroethylene, dichloroethylene, and the like. However, up to about 30% of a monoalkanol amine based on the weight of the polyalkanol amine may be admixed with the latter amine. A good practice is to admix from 5% to about 25 of the monoalkanol amine, based on the weight of the polyalkanol amine for best over all results.
As previously stated, it is an important aspect of the present invention to effect the 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 alkylaryl sulfonic acid and the salt of the mahogany sulfonate, until a pH of between 6.5 and 9.5 is obtained, and preferably until a pH between 7.0 and 8.0 is achieved. At this point an amber colored, viscous stable solution is noted. To re duce the viscosity of the resultant solution so that it can be more easily handled, it is a good practice to incorporate a small amount usually up to 25% of an inert organic solvent into the mixture prior to neutralization. Such inert solvent include as illustrative:
perchloroethylene, Stoddard solvent, and deodorized kerosene.
To further illustrate the invention the following illustrative examples of the preferred practices are presented. These are not to be taken as limitative of the invention. Unless otherwise stated, the parts are by weight.
' EXAMPLE 1 EXAMPLE 2 To a suitable reaction mixture is admixed 44 parts of sodium mahogany sulfonate (average molecular wt. 450), 56 parts of perchloroethylene, 44 parts of dodecylbenzene sulfonic acid. Thereafter, 17.5 parts of diethanolamine are slowly added. A terminal pH of 7.4 is observed.
EXAMPLE 3 To a mixture of 44 parts of dodecylbenzenesulfonie acid is added 44 parts of sodium mahogany sulfonate in 56 parts of petroleum ether. Thereafter, 22 parts of triethanol amine are added to the latter resultant mixture. A terminal pH of 7.3 is observed.
EXAMPLE 4 To a suitable reaction vessel are added 21 parts of sodium mahogany sulfonate, 29 parts of perchloroethyl- Table I Percent Detergency Percent Percent Redepositien Wat er Solvent Detergent in Perchloroethylene Soluble R.H.
' Stain Cotton Wool Cotton Wool Removal Sodium Salt of Mahogany Sulfonate .t 20. 5 3 9 10.8 70 Example 1 Detergent 44 6S. 5 0 7. 7 100 Example 2 Detergent 45v 5 73 1. 1 7. 7 100 Example 3 Detergent, 48. 5 G7 0 7. 7 100 70 Example 4 Detergent; 29 46 6. 2 20. 5 100 70 Triethanol Amine salt; of dodecylbenzenesuliouic acid 27.3 23.8 10. 5 20. 9 65 ene, 13.3 parts of tridecylbenzene sulfonic acid. A mixture of amines, i.e., 13 parts of triethanol amine and 2.3 parts of monoisopropanol amines, is then added to the reaction vessel and the contents therein gently admixed for 30 minutes. A terminal pH of 8.1 is noted.
Enhanced detersive properties of the compositions illustrated in the table below are determined in the conventional manner involving the use of a launderorneter as described in the AATCC year book for 1955 at page 55 following. In a typicalrun a standard soiled swatch and stainless steel balls together with the highly polar drycleaning solvent perchloroethylene, containing 1% by weight of the detergent additive mixture are added to a launderometer 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 92, respectively. Percent detergency is determined by subtracting the reflectance reading of the soiled swatch and dividing this difference 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 unsoiled swatches after drycleaning. In the examples below the percent tdetergency and percent redeposition are determined in perchloroethylene solvent. v
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 by visual measurements in the formula below by adding water to a known amount of detergent dissolved in solvent until the solution shows a definite cloudiness:
amt. of water (in grams) amt. 9f gl etiegent solvent soln. (in cc.) X
percent detergent V.W.T.V.:
From Table I above, it can be readily seen that the 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.
Table II etergentz' V.W.T.V. Sodium mahogany sulfonate 0.67 Example 1 composition in perchloroethylene 2.2 Example 2 composition in perchloroethylcne 1.2 Example 3 composition in perchloroethylene 1.1
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 polar solvent compatible d etergene composition consisting essentially of:
(a) 1 part by weight of an alkali metal oil-soluble mahogany sulfonate having an average molecular weight of at least 425, and
(b) from 0.5 part to 1.5 part of a poly lower alkanol amine salt of a higher alkyl aryl sullonic acid, said amine salt being formed by reacting said poly lower alkanol amine with said higher alkyl aryl sulfonic acid in the presence of said mahogany sulfonate, and the mixture being substantially neutralized to a pH of from about 6.5 to 9.5.
2. A composition according to claim 1 in which the alkali metal oil-soluble mahogany sulfonate is sodium mahogany sulfonate and the poly lower alkanol amine salt is triethanol amine salt of dodecyl benzene sulfonic acid.
3. A polar solvent compatible detergent composition consisting essentially of: I
(a) 1 part of an alkyl metal oil-soluble mahogany s'ulfonate having an average molecular weight of at least 425, i
(b) from 0.5 part to 1.5 parts of a poly lower alkanol amine salt of a higher alkyl aryl sulfonic acid, and
(c) from about 5% to about 30% of a mono lower alkanol amine salt of a higher alkyl aryl sulfonic acid, based on the weight of the said polyalkylanol amine salt, said amine salts (b) and (c) both being formed by reacting both said poly lower alkanol amine and said mono lower alkanol amine with said higher alkyl aryl sulfonic acid in the presence of said mahogany sulfonate, and the mixture being substantially neutralized to a pH from about 6.5 to 9.5.
4. A composition according to claim 9 in which the alkali metal oil-soluble mahogany sulfonate is sodium mahogany sulfonate, the poly lower alkanol amine salt is triethanol amine salt of dodecyl benzene sulfonic acid, and the mono lower alkanol amine salt is isopropanol amine salt of dodecylbenzenesulfonic acid.
5. A process for preparing oil-soluble, detergent composition which consists essentially in the steps of: admixing in the presence of an alkali metal salt of an oil-soluble mahogany sulfonate having an average molecular Weight of at least 425, (a) a higher alkyl aryl sulfonic acid with (b) a poly lower alkanol amine until a pH between 6.5 and 9.5 is obtained and the corresponding amine salt is formed, and the components of the mixture (a) and (b) being in proportion to provide from 0.5 to 1.5 parts of amine salt per part of mahogany sulfonate.
6. The process according to claim 5 in which from about 5% to about 30% of a monoalkanolamine, based on the weight of said poly lower alkanol amine is introduced simultaneously with the latter amine.
References Cited by the Examiner UNITED STATES PATENTS 2,271,635 2/1942 Flett 252-89 2,566,298 9/1951 Irwin 252-153 3,012,969 12/1961 Minne et a1 252-153 3,091,508 5/1963 Edwards 252-89 3,101,240 8/1963 Mathews 8-142 3,163,493 12/1964 Hess 8-142 3,174,935 3/1965 Eccles et a1 252-152 X LEON D. ROSDOL, Primary Examiner.
DONALD E. CZAJA, S. E. DARDEN,
Assistant Examiners.
Claims (1)
1. A POLAR SOLVENT COMPATIBLE DETERGENE COMPOSITION CONSISTING ESSENTIALLY OF: (A) 1 PART BY WEIGHT OF AN ALKALI METAL OIL-SOLUBLE MAHOGANY SULFONATE HAVING AN AVERAGE MOLECULAR WEIGHT OF AT LEAST 425, AND (B) FROM 0.5 PART TO 1.5 PART OF A POLY LOWER ALKANOL AMINE SALT OF A HIGHER ALKYL ARYL SULFONIC ACID, SAID AMINE SALT BEING FORMED BY REACTING SAID POLY LOWER ALKANOL AMINE WITH SAID HIGHER ALKYL ARYL SULFONIC ACID IN THE PRESENCE OF SAID MAHOGANY SULFONATE, AND THE 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 |
|---|---|---|---|
| US297953A US3310498A (en) | 1963-07-26 | 1963-07-26 | Novel detergent compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US297953A US3310498A (en) | 1963-07-26 | 1963-07-26 | Novel detergent compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3310498A true US3310498A (en) | 1967-03-21 |
Family
ID=23148399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US297953A Expired - Lifetime US3310498A (en) | 1963-07-26 | 1963-07-26 | Novel detergent compositions |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3310498A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3463736A (en) * | 1966-03-04 | 1969-08-26 | Atlantic Richfield Co | Aqueous slurries of triethanolamine salts of linear alkylbenzene sulfonic acids |
| US3655572A (en) * | 1970-01-21 | 1972-04-11 | Chevron Res | Water-containing dry cleaning compositions |
| US3907496A (en) * | 1971-01-18 | 1975-09-23 | Rhone Progil | Dry cleaning various articles |
| US4102824A (en) * | 1976-06-25 | 1978-07-25 | Kao Soap Co., Ltd. | Non-aqueous detergent composition |
| FR2417545A1 (en) * | 1978-02-15 | 1979-09-14 | Kao Corp | DETERGENT COMPOSITION FOR DRY CLEANING |
Citations (7)
| 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 US297953A patent/US3310498A/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 (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3463736A (en) * | 1966-03-04 | 1969-08-26 | Atlantic Richfield Co | Aqueous slurries of triethanolamine salts of linear alkylbenzene sulfonic acids |
| US3655572A (en) * | 1970-01-21 | 1972-04-11 | Chevron Res | Water-containing dry cleaning compositions |
| US3907496A (en) * | 1971-01-18 | 1975-09-23 | Rhone Progil | Dry cleaning various articles |
| US4102824A (en) * | 1976-06-25 | 1978-07-25 | Kao Soap Co., Ltd. | Non-aqueous detergent composition |
| FR2417545A1 (en) * | 1978-02-15 | 1979-09-14 | Kao Corp | DETERGENT COMPOSITION FOR DRY CLEANING |
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