US2567159A - Wetting and detergent composition - Google Patents
Wetting and detergent composition Download PDFInfo
- Publication number
- US2567159A US2567159A US125661A US12566149A US2567159A US 2567159 A US2567159 A US 2567159A US 125661 A US125661 A US 125661A US 12566149 A US12566149 A US 12566149A US 2567159 A US2567159 A US 2567159A
- Authority
- US
- United States
- Prior art keywords
- salts
- sulfosuccinate
- monoalkyl
- water
- chromium
- 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 19
- 239000003599 detergent Substances 0.000 title claims description 10
- 238000009736 wetting Methods 0.000 title description 6
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims description 37
- 239000011149 active material Substances 0.000 claims description 3
- 150000001844 chromium Chemical class 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 18
- -1 alkyl radical Chemical class 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000843 powder Substances 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 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 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 230000003381 solubilizing effect Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000003868 ammonium compounds Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000002585 base Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 2
- 229910052939 potassium sulfate Inorganic materials 0.000 description 2
- 235000011151 potassium sulphates Nutrition 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BWQKUPUNPGZPLB-UHFFFAOYSA-L S(=O)(=O)(O)C(C(=O)OCCCCCCCCCCCCCCCC)CC(=O)[O-].[Na+].[Na+].C(CCCCCCCCCCCCCCC)OC(C(CC(=O)[O-])S(=O)(=O)O)=O Chemical compound S(=O)(=O)(O)C(C(=O)OCCCCCCCCCCCCCCCC)CC(=O)[O-].[Na+].[Na+].C(CCCCCCCCCCCCCCC)OC(C(CC(=O)[O-])S(=O)(=O)O)=O BWQKUPUNPGZPLB-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- OGXRULUQTHSMSF-UHFFFAOYSA-H butanedioate chromium(3+) Chemical compound [Cr+3].[Cr+3].[O-]C(=O)CCC([O-])=O.[O-]C(=O)CCC([O-])=O.[O-]C(=O)CCC([O-])=O OGXRULUQTHSMSF-UHFFFAOYSA-H 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229960000359 chromic chloride Drugs 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 235000007831 chromium(III) chloride Nutrition 0.000 description 1
- 239000011636 chromium(III) chloride Substances 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- UZDWIWGMKWZEPE-UHFFFAOYSA-K chromium(iii) bromide Chemical compound [Cr+3].[Br-].[Br-].[Br-] UZDWIWGMKWZEPE-UHFFFAOYSA-K 0.000 description 1
- PKULCESNTQFEEL-UHFFFAOYSA-N diazanium;2-sulfobutanedioate Chemical class [NH4+].[NH4+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O PKULCESNTQFEEL-UHFFFAOYSA-N 0.000 description 1
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
- GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical class [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000002156 mixing 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
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/02—Organic and inorganic agents containing, except water
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
- Y10S516/04—Protein or carboxylic compound containing
Definitions
- Patented Ifi 4 l95l WE'KTKNG AND DETERGENT CUIWIPOSII'E'ION Emil ll. Vitalis, Springdale, 0011111., assignor to American tlyanarnid (Jompany, New York, N. Y a corporation oi Maine No Brag. Application November 4, 1949, Serial No. 125,661
- This invention relates to wetting and detergent compositions containing monoalkyl suliosuccinates together with solubillzing agents therefor.
- the invention includes the compositions themselves, their methods of preparation, and wetting and detergent processes in which these compositions are used.
- a further object resides in the provision of readily soluble pastes or powders containin the higher monoalkyl sulfosuccinates in a solubilized and therefore Water-dispersible condition. Still further objects of the invention will be apparent from the following detailed description of preferred embodiments thereof.
- the sodium, potassium, ammonium, ethanolamine and similar salts of the higher monoalkyl sulfosuccinates in which the alkyl radical contains 12 or more carbon atoms are only slightly soluble in water.
- the solubility of the disodium salts which is given in the following table, is typical of the corresponding salts of potassium and ammonium as well.
- water-soluble chromium salts such as chromium sulfate, chromium chloride, chromium nitrate, and the like are excellent solubilizing agents for the higher monoalkyl sulfosuccinate salts.
- I have found, however, that I can prepare stable aqueous solutions containing from about 1% to about 30% of the wetting agents, depending on the particular alcohol present in the sulfosuccinate ester, as well as water-soluble concentrated aqueous pastes containin about 30-70% of the wetting agents, and even water-soluble dry powders containing the higher monoalkyl sulfosuccinate salts together with inorganic salts of the type of sodium sulfate, sodium chloride and the like by incorporating therein suitable quantities of chromium salts which ionize in aqueous solution.
- the monoalkyl sulfosuccinate salts which are solubilized by chromium salts in accordance with the present invention have the following formula MOaS.C.COOM
- M is a monovalent salt-forming group such as sodium, potassium, ammonium, ethanolamine and'the like
- R is an alkyl radical, of at least 12 carbon atoms and preferably 12 to 18 carbon atoms which may be saturated or unsaturated, or a mixture of such alkyl radicals.
- the compounds defined by the above formula are preferably prepared by esteriiying maleic anhydride or maleic acid with dodecyl, tetradecyl, octadecyl, octadecenyl or other alcohols containing 12 or more carbon atoms at about loll- C.
- the sulfonation is carried out by heating the ester with an aqueous solution of sodium sulfite, or sodium metabisulfite, or of the corresponding potassium or ammonium compounds.
- the alkali metal and ammonium salts of the monoalkyl sulfosuccinic acid esters are obtained directly.
- the corresponding salts of ethanolamine and other bases are preferably produced by first acidifying an alcoholic solution of the alkali metal or ammonium sulfosuccinates, whereby the free sulfosuccinic acid monoester is obtained, filtering off the inorganic salt of the acid used and reacting the sulfosuccinic acid ester with the desired base.
- Salts of other metals such as calcium, barium, zinc, tin, lead and the like are prepared by adding stoichiometric quantities of their oxides or hydroxides to the alcoholic sulfosuccinic acid monoester followed by stirringuntil the salt formation is complete.
- Salts of organic bases such as methylamine, ethylamine, ethanolamine and the like may also be prepared by the same method.
- the higher monoalkyl sulfosuccinates in the form of dry, water-dispersible powders.
- this has not been possible, for upon evaporation of their solutions in water or organic solvents the compounds form a white pasty mass similar in texture to ordinary soap.
- the compounds are precipitated from their aqueous solutions by the addition of ammonium, sodium, or potassium salts, and therefore the addition of sodium or potassium sulfate or chloride to form a dry, freeflowing powder could not be resorted to.
- Another important feature of the present invention is the discovery that the solubilizing action of water-soluble chromium salts persists even in the presence of sodium sulfate, sodium chloride and other salts which would ordinarily precipitate the higher monoalkyl sulfosuccinate salts from their water solutions.
- This discovery has enabled me to prepare dry, free-flowing powders containing the higher monoalkyl sulfosuccinate salts in admixture with water-soluble alkali metal compounds, or in admixture with watersoluble ammonium compounds, which powders are readily soluble in cold water. No material change in the ratio of chromium salt to monoallryl sulfosuccinate salt need be made when other water-soluble salts are added; i.
- the solubilizing action of the chromium salts is the same in the presence of sodium sulfate, sodium chloride and the like as it is in the absence of these salts.
- the upper limit of diluent which may be employed depends entirely on the desired concentration of wetting agent in the dry mixture, the lower limit of diluent is not substantially less than 40% of the mixture.
- the material is not easily soluble in cold water; for this reason dry mixtures containing in excess of about 60% 'of monoalkyl sulfosuccinate are not included within the purview of this invention.
- the amounts of chromium salts to be employed vary according to the original water solubility of the various monoalkyl sulfosuccinate salts. It will be readily apparent that dodecyl disodium sulfosuccinate, having a water solubility of 4.5 grams per 100 cc., will require the addition of less chromium salt than will disodium hexadecyl sulfosuccinate, for
- the sulfosuccinate mixture above referred to is that prepared from Ammecol.
- chromium salt addition since the solubilizing agent does not interfere with the wetting and detergent properties of the monoalkyl sulfosuccinates, for most commercial applications not more than about 7 to 10 mols of chromium salt should be employed for each mol of sulfosuccinate.
- the most preferable quantity of chromium salt to be employed is from 0.25 mol to 1 mol for each mol of the sulfosuccinate depending on its water solubility.
- chromium salts may of course be used, although amounts substantially larger than those given in the above table are not usually necessary.
- Example 1 A paste was prepared by mixing together 95 parts of a 30% aqueous gel of a disodium monoalkyl sulfosuccinate prepared from Ammecol, and 5 parts of CI2(SO4)3. The paste was used to prepare an aqueous solution containing 9% of the sulfosuccinate salt. The material was completely soluble and the solution remained clear at temperatures of from 6-10 0., whereas the same sul- Example 2 A dry, free-flowing powder was obtained by drying to 100 parts an aqueous mixture consisting of 116 parts of a 30% aqueous gel of the disodium monoalkyl sulfosuccinate mixture employed in Example 1, 6 parts of CI2(SO4)3, and 69 parts of N82SO4. The dried powder formed clear solutions with water when used in concentrations up to 9%.
- Example 3 To 100 cc. of a 2% aqueous dispersion of dipotassium cetyl sulfosuccinate was added 7.2 cc. of a 10% CIC13.6H2O solution (1:0.67 molar ratio). Within a short period of time the initially cloudy dispersion became clear, indicating that a true solution of the sulfosuccinate had been obtained.
- Example 4 To 100 cc. of a 2% aqueous dispersion of diammonium cetyl sulfosuccinate was added 11.0 cc. of a 10% C1(NO3)3.7H2O solution (1:0.67 molar ratio). Within a short period of time the initially cloudy dispersion became clear, indicating that a true solution of the sulfosuccinate had been obtained.
- Example 5 To 100 cc. of a 5% aqueous dispersion of disodium oleyl sulfosuccinate was added 7.5 cc. of a CrClzfiHzO solution (1:0.67 molar ratio). Within a short period of time the initially cloudy dispersion became clear, indicating that a true solution of the sulfosuccinate had been obtained.
- chromic bromide suitably solubilize the higher monoalkyl suli'osuccinates similarly to chromic chloride.
- Example 6 A W ting and detergent composition 1 t1.
- a surface active material which is a monoalkyl suliosuccinate having the formula H MOri-COOM COOR in which M i a member of the group consisting of alkali metal and ammonium radicals and both M' are the same, and R is an alkyl radical of from 12 to 18 carbon atoms, and a water-soluble inorganic chromium salt which is capableof increasing the water solubility of the monoalkyl suliosuccinate, said chromium salt being present in an amount the minimum range of which is from 0.25 mol to 1 mol and the maximum amount is 10 mols for each mol of the sulfosuccinate.
- a wetting and detergent composition comprising essentially a. surface active material which is a mixture of monoalkyl sulfosuccinates having the formula H MOaS.$.COOM
- M is a member of the group consisting of alkali metal and ammonium radicals and both Ms are the same
- R. is an alkyl radical of from 12 to 18 carbon atoms
- a watersoluble inorganic chromium salt which is capable of increasing the water olubility of the mixture of monoalkyl sulfosuccinates, said chromium salt being present in an amount the minimum range of which is from 0.25 mol to 1 mol and the maximum amount is 10 mols for each mol of the sulfosuccinates.
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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)
Description
Patented Ifi 4, l95l WE'KTKNG AND DETERGENT CUIWIPOSII'E'ION Emil ll. Vitalis, Springdale, 0011111., assignor to American tlyanarnid (Jompany, New York, N. Y a corporation oi Maine No Brag. Application November 4, 1949, Serial No. 125,661
2 Clo.
This invention relates to wetting and detergent compositions containing monoalkyl suliosuccinates together with solubillzing agents therefor. The invention includes the compositions themselves, their methods of preparation, and wetting and detergent processes in which these compositions are used.
It is known that the higher monoalkyl sulfosuccinates, when used in the form of their salts with monovalent salt-forming compounds, possess good Wetting and particularly good detergent properties. However, the salts of monoesters of suliosuccinic acid with alcohols of 12 or more carbon atoms, which is the minimum chain length for good detergency, possess relatively low solubility in water, which is a serious disadvantage. It is a principal object of the present invention to provide for this class of compounds solubilizing agents which improve their water solubility and thus increase their usefulness as wetting agents and detergents. A further object resides in the provision of readily soluble pastes or powders containin the higher monoalkyl sulfosuccinates in a solubilized and therefore Water-dispersible condition. Still further objects of the invention will be apparent from the following detailed description of preferred embodiments thereof.
As is noted above the sodium, potassium, ammonium, ethanolamine and similar salts of the higher monoalkyl sulfosuccinates in which the alkyl radical contains 12 or more carbon atoms are only slightly soluble in water. The solubility of the disodium salts, which is given in the following table, is typical of the corresponding salts of potassium and ammonium as well.
Solubility,
Monoalkyl Disodium Sulfosuccinate gins [100 cc.
of Solution DodecyL 4. 5 TctradecyL 0. 05 Hcxadecyl- 0. 2 Octadecyl 0. 05
carbon nature boiling at 39 C. to 96 C. at 0.3 mm. of mercury pressure and therefore containing about 14-16 carbon atoms, and about 58% of higher boiling materials, possibly higher alcohols. This mixture is hereinafter designated as Ammeco which is its commercial name.
Attempts have been made to solubilize these and similar compounds by addin water-soluble alcohols, ethers of ethylene glycol and other agents which are known to solubilize the higher dialkyl sulfosuccinates. However, it was found that these alcohols and ethers actually reduce the water solubility of the alkali metal and ammonium salts of higher monoallryl sulfosuccinates.
I have now discovered that water-soluble chromium salts such as chromium sulfate, chromium chloride, chromium nitrate, and the like are excellent solubilizing agents for the higher monoalkyl sulfosuccinate salts. This is a remarkable discovery, for the addition of the corresponding salts of alkali metals such as sodium or potassium sulfate or chloride causes precipitation of the higher monoalkyl sulfosuccinate salts instead of solubilizing them. I have found, however, that I can prepare stable aqueous solutions containing from about 1% to about 30% of the wetting agents, depending on the particular alcohol present in the sulfosuccinate ester, as well as water-soluble concentrated aqueous pastes containin about 30-70% of the wetting agents, and even water-soluble dry powders containing the higher monoalkyl sulfosuccinate salts together with inorganic salts of the type of sodium sulfate, sodium chloride and the like by incorporating therein suitable quantities of chromium salts which ionize in aqueous solution.
The monoalkyl sulfosuccinate salts which are solubilized by chromium salts in accordance with the present invention have the following formula MOaS.C.COOM
-JJOOR H2 in which M is a monovalent salt-forming group such as sodium, potassium, ammonium, ethanolamine and'the like, and R is an alkyl radical, of at least 12 carbon atoms and preferably 12 to 18 carbon atoms which may be saturated or unsaturated, or a mixture of such alkyl radicals. The compounds defined by the above formula are preferably prepared by esteriiying maleic anhydride or maleic acid with dodecyl, tetradecyl, octadecyl, octadecenyl or other alcohols containing 12 or more carbon atoms at about loll- C. to form the monoester, followed by suli'onating this ester to form the sulfosuccinate. Preferably the sulfonation is carried out by heating the ester with an aqueous solution of sodium sulfite, or sodium metabisulfite, or of the corresponding potassium or ammonium compounds. By this method the alkali metal and ammonium salts of the monoalkyl sulfosuccinic acid esters are obtained directly.
The corresponding salts of ethanolamine and other bases are preferably produced by first acidifying an alcoholic solution of the alkali metal or ammonium sulfosuccinates, whereby the free sulfosuccinic acid monoester is obtained, filtering off the inorganic salt of the acid used and reacting the sulfosuccinic acid ester with the desired base. Salts of other metals such as calcium, barium, zinc, tin, lead and the like are prepared by adding stoichiometric quantities of their oxides or hydroxides to the alcoholic sulfosuccinic acid monoester followed by stirringuntil the salt formation is complete. Salts of organic bases such as methylamine, ethylamine, ethanolamine and the like may also be prepared by the same method.
For many purposes it is desirable to prepare the higher monoalkyl sulfosuccinates in the form of dry, water-dispersible powders. Heretofore this has not been possible, for upon evaporation of their solutions in water or organic solvents the compounds form a white pasty mass similar in texture to ordinary soap. The compounds are precipitated from their aqueous solutions by the addition of ammonium, sodium, or potassium salts, and therefore the addition of sodium or potassium sulfate or chloride to form a dry, freeflowing powder could not be resorted to.
Another important feature of the present invention is the discovery that the solubilizing action of water-soluble chromium salts persists even in the presence of sodium sulfate, sodium chloride and other salts which would ordinarily precipitate the higher monoalkyl sulfosuccinate salts from their water solutions. This discovery has enabled me to prepare dry, free-flowing powders containing the higher monoalkyl sulfosuccinate salts in admixture with water-soluble alkali metal compounds, or in admixture with watersoluble ammonium compounds, which powders are readily soluble in cold water. No material change in the ratio of chromium salt to monoallryl sulfosuccinate salt need be made when other water-soluble salts are added; i. e., the solubilizing action of the chromium salts is the same in the presence of sodium sulfate, sodium chloride and the like as it is in the absence of these salts. However, it has been found that while the upper limit of diluent which may be employed depends entirely on the desired concentration of wetting agent in the dry mixture, the lower limit of diluent is not substantially less than 40% of the mixture. For example, when a dry mix is prepared containing more than about 60% of the monoalkyl sulfosuccinate, the material is not easily soluble in cold water; for this reason dry mixtures containing in excess of about 60% 'of monoalkyl sulfosuccinate are not included within the purview of this invention.
Inpraeticing the invention, the amounts of chromium salts to be employed vary according to the original water solubility of the various monoalkyl sulfosuccinate salts. It will be readily apparent that dodecyl disodium sulfosuccinate, having a water solubility of 4.5 grams per 100 cc., will require the addition of less chromium salt than will disodium hexadecyl sulfosuccinate, for
ill
Per Cent Per Cent Solubility, Solubility, Molar Ratio, gms./l00 cc. gmsJlOO cc. Chromium at 30 0., No at 30 0., to Succinate Chromium Crz(S0|): Salt Salt Addu. Added Dodccyl 4. 5 8 2/511 Dodecyl 4. 5 20 3/5zl Tctradecyl. 0.05 5 3/511 Hexadecyl. 0. 2 10 3 :l Mixture 0. 2 9 315:! Octadccyl. 0.05 2 1:1
The sulfosuccinate mixture above referred to is that prepared from Ammecol.
As is common in the case of the solubility of salts, higher solution temperatures result in an increase of the solubility of the various salts. In the case of the present invention, such variations in solution temperatures permit the use of smaller amounts-of the solubilizing chromium salts. For this reason, the lower limits of such salt additions may in some cases and for some purposes be within the range of from 0.25 mol to 0.5 mol per mol of sulfosuccinate salt employed. On the other hand, while there is no absolute upper limit of chromium salt addition since the solubilizing agent does not interfere with the wetting and detergent properties of the monoalkyl sulfosuccinates, for most commercial applications not more than about 7 to 10 mols of chromium salt should be employed for each mol of sulfosuccinate. Moreover, I have found that the most preferable quantity of chromium salt to be employed is from 0.25 mol to 1 mol for each mol of the sulfosuccinate depending on its water solubility.
Conversely, in preparing aqueous pastes and dry powders containing water-soluble inorganic salts of monovalent metals such as sodium and potassium, larger amount of chromium salts may of course be used, although amounts substantially larger than those given in the above table are not usually necessary.
It is evident, therefore, that the invention in its broader aspects is not limited to the use of large quantities of the chromium salts but that relatively small proportions of these salts may be used if desired.
The invention will be illustrated in greater detail by the following specific examples. It should be understood, however, that although these examples may describe in detail certain specific features of the invention, they are given primaril for purposes of illustration and the invention in its broader aspects is not limited thereto. All parts iven are by weight.
Example 1 A paste was prepared by mixing together 95 parts of a 30% aqueous gel of a disodium monoalkyl sulfosuccinate prepared from Ammecol, and 5 parts of CI2(SO4)3. The paste was used to prepare an aqueous solution containing 9% of the sulfosuccinate salt. The material was completely soluble and the solution remained clear at temperatures of from 6-10 0., whereas the same sul- Example 2 A dry, free-flowing powder was obtained by drying to 100 parts an aqueous mixture consisting of 116 parts of a 30% aqueous gel of the disodium monoalkyl sulfosuccinate mixture employed in Example 1, 6 parts of CI2(SO4)3, and 69 parts of N82SO4. The dried powder formed clear solutions with water when used in concentrations up to 9%.
Example 3 To 100 cc. of a 2% aqueous dispersion of dipotassium cetyl sulfosuccinate was added 7.2 cc. of a 10% CIC13.6H2O solution (1:0.67 molar ratio). Within a short period of time the initially cloudy dispersion became clear, indicating that a true solution of the sulfosuccinate had been obtained.
Example 4 To 100 cc. of a 2% aqueous dispersion of diammonium cetyl sulfosuccinate was added 11.0 cc. of a 10% C1(NO3)3.7H2O solution (1:0.67 molar ratio). Within a short period of time the initially cloudy dispersion became clear, indicating that a true solution of the sulfosuccinate had been obtained.
Example 5 To 100 cc. of a 5% aqueous dispersion of disodium oleyl sulfosuccinate was added 7.5 cc. of a CrClzfiHzO solution (1:0.67 molar ratio). Within a short period of time the initially cloudy dispersion became clear, indicating that a true solution of the sulfosuccinate had been obtained.
It has also been found that chromic bromide suitably solubilize the higher monoalkyl suli'osuccinates similarly to chromic chloride.
Example 6 A W ting and detergent composition 1 t1.
prising essentially a surface active material which is a monoalkyl suliosuccinate having the formula H MOri-COOM COOR in which M i a member of the group consisting of alkali metal and ammonium radicals and both M' are the same, and R is an alkyl radical of from 12 to 18 carbon atoms, and a water-soluble inorganic chromium salt which is capableof increasing the water solubility of the monoalkyl suliosuccinate, said chromium salt being present in an amount the minimum range of which is from 0.25 mol to 1 mol and the maximum amount is 10 mols for each mol of the sulfosuccinate.
2. A wetting and detergent composition comprising essentially a. surface active material which is a mixture of monoalkyl sulfosuccinates having the formula H MOaS.$.COOM
.COOR
in which M is a member of the group consisting of alkali metal and ammonium radicals and both Ms are the same, and R. is an alkyl radical of from 12 to 18 carbon atoms, and a watersoluble inorganic chromium salt which is capable of increasing the water olubility of the mixture of monoalkyl sulfosuccinates, said chromium salt being present in an amount the minimum range of which is from 0.25 mol to 1 mol and the maximum amount is 10 mols for each mol of the sulfosuccinates.
EMIL A. VITALIS.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,181,087 Caryl et a1 Nov. 21, 1939 2,316,234 Flett Apr. 13, 1943 OTHER REFERENCES Aerosol Wetting Agents, publication of Amer. Cyanamid and Chem. Corp., N. Y., (1941). DD.
Claims (1)
1. A WETTING AND DETERGENT COMPOSITION COMPRISING ESSENTIALLY A SURFACE ACTIVE MATERIAL WHICH IS A MONOALKYL SULFOSUCCINATE HAVING THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US125661A US2567159A (en) | 1949-11-04 | 1949-11-04 | Wetting and detergent composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US125661A US2567159A (en) | 1949-11-04 | 1949-11-04 | Wetting and detergent composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2567159A true US2567159A (en) | 1951-09-04 |
Family
ID=22420815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US125661A Expired - Lifetime US2567159A (en) | 1949-11-04 | 1949-11-04 | Wetting and detergent composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2567159A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2917431A (en) * | 1957-08-01 | 1959-12-15 | American Cyanamid Co | Aqueous inorganic salt-sulfosuccinate solutions |
| US3901832A (en) * | 1965-08-24 | 1975-08-26 | Colgate Palmolive Co | Detergent cake containing monoalkylsulfosuccinate and preparation |
| US4746382A (en) * | 1986-09-05 | 1988-05-24 | Swing Paints, Ltd. | Composition to improve adhesiveness of prepasted wallpaper and method of use |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2181087A (en) * | 1937-07-07 | 1939-11-21 | American Cyanamid & Chem Corp | Detergent composition |
| US2316234A (en) * | 1940-11-30 | 1943-04-13 | Allied Chem & Dye Corp | Ester of sulphosuccinic acid |
-
1949
- 1949-11-04 US US125661A patent/US2567159A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2181087A (en) * | 1937-07-07 | 1939-11-21 | American Cyanamid & Chem Corp | Detergent composition |
| US2316234A (en) * | 1940-11-30 | 1943-04-13 | Allied Chem & Dye Corp | Ester of sulphosuccinic acid |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2917431A (en) * | 1957-08-01 | 1959-12-15 | American Cyanamid Co | Aqueous inorganic salt-sulfosuccinate solutions |
| US3901832A (en) * | 1965-08-24 | 1975-08-26 | Colgate Palmolive Co | Detergent cake containing monoalkylsulfosuccinate and preparation |
| US4746382A (en) * | 1986-09-05 | 1988-05-24 | Swing Paints, Ltd. | Composition to improve adhesiveness of prepasted wallpaper and method of use |
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