US2427576A - Ether sulphonates and their production - Google Patents

Ether sulphonates and their production Download PDF

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US2427576A
US2427576A US579315A US57931545A US2427576A US 2427576 A US2427576 A US 2427576A US 579315 A US579315 A US 579315A US 57931545 A US57931545 A US 57931545A US 2427576 A US2427576 A US 2427576A
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sulphonate
alcohol
salt
aliphatic
halogen
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US579315A
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Smith Ralph Carlisle
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Colgate Palmolive Co
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Colgate Palmolive Peet Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
    • C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
    • 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

Definitions

  • This invention relates to the preparation of new chemical substances which are eflicient wetin contact with strong acids or alkali.
  • Agents such as sodium lauryl sulphate, in the presence of hot, strong, caustic soda, will be converted to the corresponding alcohcl,'lauryl alcohol, and an inorganic sulphate, sodium sulphate.
  • fattyacid soaps in a strong acid solution will be split to a fatty acid and an inorganic salt.
  • the fatty acid esters of isethionic acid are de-esterified in contact with either strong acid or strong alkali and hence are not completely satisfactory.
  • these compounds contain, at least eight carbon atoms, they are excellent Wetting, emulsifying and deterging compounds which are operative in hard, soft or sea water whether hot or cold. They can be used for any purpose that other wetting, washing and emulsifying agents are used for, and they possess the added advantages of stability and high solubility.
  • novel compounds of this invention are aliphatic ethers of hydroxy and/or halogenated aliphatic sulphonates. These compounds fall within the class of compounds having the formula (RF-Z) m-X--(SO3) Y, wherein R is an aliphatic hydrocarbon radical; Z is oxygen; X is a hydroxy and/or halogen substituted aliphatic radical; Y is a cation; and m and n are small whole numbers.
  • It may also be prepared by the action of an alkali metal, an alkaline earth metal, magnesium, aluminum or zinc, or their amalgams, oxides, hydroxides or reactive salts, on the aliphatic alcohols at atmospheric or elevated temperatures and pressures, with or without non-reactive solvents.
  • These aliphatic alcohols preferably contain at least six carbon atoms and saturated straight chains.
  • halogen alkyl hydroxy sulphonates or polyhalogen alkyl sulphonates may be obtained from any source. They may be prepared according to the procedure of Darmstaedter in Liebigs Ann. Chem. 148, 126 (1868), or according to the process given in Ross U. S. Patent No. 2,195,581.
  • the preferred reactants are 3 chlor, 2 hydroxy, propane sulphonic acid sodium salt, and 2, 3 dichlor propane sulphonic acid sodium salt.
  • the final ether compound have the ether linkage at one end of the substituted alkyl sulphonate compound and have a halogen or hydroxy group substituted on a carbon adjacent to that having the sulphonate substitution, and further that these groups be at the other end of the molecular structure, since the products of such constitution possess the best emulsifying and hydrophilic properties. It is also preferred that the aliphatic constituents having the sulphonate and hydroxy and/or halogen substitutions have not more than six carbon atoms.
  • One way of preparing these compounds may be by dissolving a dry alcohol in a suitable solvent, such as toluene or xylene. To this solution is added an equivalent weight of an alkali metal or amide, such as sodium or sodamide, based on the mols of alcohol used. When sodamide is used, the solution is refluxed until ammonia vapor ceases to evolve, thus showing substantially complete conversion of the alcohol to an alcoholate.
  • a suitable solvent such as toluene or xylene.
  • an equivalent weight of an alkali metal or amide such as sodium or sodamide
  • a halogen alkyl hydroxy or halogen sulphonate salt is then added to the alkaline solution and the mixture is again refluxed with thorough agitation until the alkyl hydroxy or halogen sulphonate ether is formed.
  • the solvent is removed by vacuum distillation.
  • the products may be rendered free from byproduct salts by treatment with ethyl alcohol,
  • a salt product of the present invention may be interchanged with the cation of an inorganic salt by treating a solution of one or more salts of the organic product in one or more of the above named solvents with an excess of a concentrated aqueous solution of a salt of that cation which is to be exchanged for the original product salt cation. It should be noted that any of the products falling within the scope of the present invention may be neutralized and purified by the above outlined procedure.
  • Example A solution of 18.6 parts of lauryl alcohol dissolved in 75 parts of toluene is refluxed with 4 parts of powdered sodamide until no further ammonia is evolved.
  • Twenty parts of the sodium salt of. gamma chlor, beta hydroxy propane sulphonic acid are added to the alkaline solution and the mixture refluxed for about twelve hours while vigorously stirring.
  • the toluene is removed by vacuum distillation and the residue is taken up with'water and extracted with butyl alcohol to remove the active ingredient from the sodium chloride.
  • a mono-lauryl ether of beta hydroxy propane sulphonic acid sodium salt is obtained.
  • 2, 3 dichlor propane sulphonicacid sodium salt may be substituted for the sodium salt of gamma chlor, beta hydroxy propane sulphonic acid, whereby a mono-lauryl ether of beta chlor propane sulphonic acid sodium salt is obtained.
  • Potassium cetylate may similarly be reacted with anhydrous dichlor propane potassium sulphonate. That is, likewise, using molecular quantities of the reactants, a solution of about twenty-four parts of cetyl alcohol dissolved in about seventy-five or more parts of toluene is refluxed with about six parts of powdered potassamide until no further ammonia is evolved. About twenty-three parts of anhydrous 2, 3 dichlor propane potassium sulphonate are added to the alkaline solution and the mixture refluxed for about twelve hours while vigorously stirring.
  • toluene is removed by vacuum distillation and the residue is taken up with water and extracted with butyl alcohol to remove the active ingredient from the potassium chloride. Upon evaporation of the butyl alcohol, a monocetyl It is preferred to pre- 4 ether of beta chlor propane sulphonic acid potassium salt is obtained.
  • the aliphatic alcohols or alcoholates may be straight or branched chain, saturated or unsaturated, and may be of primary, secondary or tertiary alcohols. Furthermore, they may be of monoor poly-hydroxy substances.
  • the suitable substances include the following alcohols or alcoholates thereof; myristyl alcohol, carnaubyl alcohol, octadecyl alcohol, oleyl alcohol, myricyl alcohol, tertiary amyl alcohol, abietyl alcohol, polyglycol, benzyl alcohol, cyclohexanol, and mixtures thereof.
  • Mixed alcoholates such as those of alcohols produced by reduction of the coconut oil fatty acids, may be used.
  • the halogen alkyl sulphonates can be monoor poly-hydroxy and/or halogen substituted, which thus permits the preparation of polyethers.
  • poly is meant two or more.
  • the free sulphonic acids can be prepared by treating the compound with a dilute mineral acid.
  • halogen and/or hydroxy sulphonate ethers are extremely stable in both alkaline and acid solutions. They are excellent detergents and emulsifiers and find use as domestic cleaning compositions, degreasing compounds, hard water detergents, etc.
  • the presence of the halogen or hydroxy group materially increases the solubility and eflicacy of the compound.
  • the new materials possess unusual deterging, sudsing and water-softening properties by themselves, they may be used with other emulsifying agents, including soaps, rosinates, long chain alcohol sulphates, alkylated aromatic sulphonic acid salts, sulphonated mineral oil extracts, Turkey red oil, lecithin, glycerolamines, monoethanolamine, diethanolamine and trieethanolamine; coloring matter, such as dyes, lakes and pigments; abrasives and inert fillers, such as silica, pumice, feldspar, precipitated chalk,
  • the type of addition agent to'be used will depend on the ultimate use
  • the final detergent composition may be formed into beads, flakes, bars, chips, crystals, powders,
  • softeners deodorants and disinfectants
  • water paints and polishes sizes, glues and adhesives, such as shellac and casein compositions; liquid solid and paste tooth and mouth detergents, laundry detergents and other textile agents, in-
  • the process which comprises reacting, in an alkaline condition, a polyhalogen alkyl sulphonate having not more than six carbon atoms with an aliphatic alcoholic compound having at least six carbon atoms of the group consisting of alcoholates and alcohols.
  • the process which comprises reacting, under substantially anhydrous alkaline conditions, a 2,3 (ii-halogen propane sulphonate salt with a long chain aliphatic alcoholate having at least six carbon atoms, to yield a long chain ether of a halogen substituted propane sulphonate salt.
  • R. is an aliphatic hydrocarbon radical having at least six carbon atoms
  • Z is oxygen
  • X is an aliphatic radical substituted by at least one halogen group
  • Y is a cation
  • m and n are small whole numbers.
  • a lauryl ether of a chlorpropane sulphonate salt 9.
  • a cetyl ether of a chlorpropane sulphonate salt 10.
  • the process which comprises reacting, in an alkaline condition, a polyhalogen alkyl sulphonate with a cetyl alcohol compound of the group consisting of alcoholates and alcohols.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Patented Sept. 16, 1947 ETHER SULPHONATES AND THEIR PRODUCTION Ralph Carlisle Smith, Jersey City, N. J., assignor to Colgate-Palmolive-Peet Company, Jersey City, N. J., a corporation of Delaware No Drawing. Application February 22, 1945, Serial No. 579,315
12 Claims. (Cl. 260--513) This invention relates to the preparation of new chemical substances which are eflicient wetin contact with strong acids or alkali. Agents such as sodium lauryl sulphate, in the presence of hot, strong, caustic soda, will be converted to the corresponding alcohcl,'lauryl alcohol, and an inorganic sulphate, sodium sulphate. On the other hand, fattyacid soaps in a strong acid solution will be split to a fatty acid and an inorganic salt. The fatty acid esters of isethionic acid are de-esterified in contact with either strong acid or strong alkali and hence are not completely satisfactory. M
In addition, it has been noted that a simple aliphatic sulphonate does not have wholly satisfactory hydrophilic properties, but that the presence of one or more hydroxy and/or halogen groups in the molecule, relatively close to a sulquite stable in both acid and alkaline solutions.
It has further been discovered that if these compounds contain, at least eight carbon atoms, they are excellent Wetting, emulsifying and deterging compounds which are operative in hard, soft or sea water whether hot or cold. They can be used for any purpose that other wetting, washing and emulsifying agents are used for, and they possess the added advantages of stability and high solubility.
The novel compounds of this invention are aliphatic ethers of hydroxy and/or halogenated aliphatic sulphonates. These compounds fall within the class of compounds having the formula (RF-Z) m-X--(SO3) Y, wherein R is an aliphatic hydrocarbon radical; Z is oxygen; X is a hydroxy and/or halogen substituted aliphatic radical; Y is a cation; and m and n are small whole numbers.
These compounds are readily and economically prepared by the novel process of the present invention. It has now been found that the reaction between an alcoholate and a sulphonate of an aliphatic compound having at least one halogen and at least one additional halogen and/or hydroxy group substituted therein produces an aliphatic ether of a halogen and/or hydroxy substituted alkyl sulphonate. The source of the aliphatic alcoholate is immaterial, and it may be prepared by the action of sodium, sodium amalgam, sodamide, or other metals, amalgams or amides, on alcohols, preferably in a solvent such as benzene, toluene, xylene or molten parafiin. It may also be prepared by the action of an alkali metal, an alkaline earth metal, magnesium, aluminum or zinc, or their amalgams, oxides, hydroxides or reactive salts, on the aliphatic alcohols at atmospheric or elevated temperatures and pressures, with or without non-reactive solvents. These aliphatic alcohols preferably contain at least six carbon atoms and saturated straight chains.
The halogen alkyl hydroxy sulphonates or polyhalogen alkyl sulphonates may be obtained from any source. They may be prepared according to the procedure of Darmstaedter in Liebigs Ann. Chem. 148, 126 (1868), or according to the process given in Ross U. S. Patent No. 2,195,581. The preferred reactants are 3 chlor, 2 hydroxy, propane sulphonic acid sodium salt, and 2, 3 dichlor propane sulphonic acid sodium salt. It is preferred that the final ether compound have the ether linkage at one end of the substituted alkyl sulphonate compound and have a halogen or hydroxy group substituted on a carbon adjacent to that having the sulphonate substitution, and further that these groups be at the other end of the molecular structure, since the products of such constitution possess the best emulsifying and hydrophilic properties. It is also preferred that the aliphatic constituents having the sulphonate and hydroxy and/or halogen substitutions have not more than six carbon atoms.
One way of preparing these compounds may be by dissolving a dry alcohol in a suitable solvent, such as toluene or xylene. To this solution is added an equivalent weight of an alkali metal or amide, such as sodium or sodamide, based on the mols of alcohol used. When sodamide is used, the solution is refluxed until ammonia vapor ceases to evolve, thus showing substantially complete conversion of the alcohol to an alcoholate. The temperature of reaction, of course, depends on the boiling point of the solvent being refluxed.
A halogen alkyl hydroxy or halogen sulphonate salt is then added to the alkaline solution and the mixture is again refluxed with thorough agitation until the alkyl hydroxy or halogen sulphonate ether is formed. The solvent is removed by vacuum distillation.
The products may be rendered free from byproduct salts by treatment with ethyl alcohol,
butyl alcohol, acetone, carbitol, monoglycerides,
Cellosolve, dioxane and/or the like. This may also be acomplished by preparing the calcium salt and filtering the product from the insoluble calcium sulphate. The cation of a salt product of the present invention may be interchanged with the cation of an inorganic salt by treating a solution of one or more salts of the organic product in one or more of the above named solvents with an excess of a concentrated aqueous solution of a salt of that cation which is to be exchanged for the original product salt cation. It should be noted that any of the products falling within the scope of the present invention may be neutralized and purified by the above outlined procedure.
'The products of the present invention appear to owe much of their effectiveness to the presence of the free hydroxy group or groups and/or halogen group or groups in the residue of the aliphatic polyhydroxy substance. The solubility,
and the foaming, wetting and washing efficiency,
seem to be intimately associated with the structure of the compound. Furthermore, this grouping containing hydroxy radicals seems to reduce materially the tendency of the products to dust when formed into powders, beads, bubbles, flakes, ribbons, chips, or fibres. pare the products from substituted short chain alkyl sulphonate salts, since these materials are more readily and economically prepared and produce more eifective products than do the long chain alkyl sulphonates.
A consideration of the following example will I give a better understanding of the invention, but
the scope of the invention is not intended to be limited thereby.
Example A solution of 18.6 parts of lauryl alcohol dissolved in 75 parts of toluene is refluxed with 4 parts of powdered sodamide until no further ammonia is evolved. Twenty parts of the sodium salt of. gamma chlor, beta hydroxy propane sulphonic acid are added to the alkaline solution and the mixture refluxed for about twelve hours while vigorously stirring. The toluene is removed by vacuum distillation and the residue is taken up with'water and extracted with butyl alcohol to remove the active ingredient from the sodium chloride. Upon evaporation of the butyl alcohol, a mono-lauryl ether of beta hydroxy propane sulphonic acid sodium salt is obtained.
2, 3 dichlor propane sulphonicacid sodium salt may be substituted for the sodium salt of gamma chlor, beta hydroxy propane sulphonic acid, whereby a mono-lauryl ether of beta chlor propane sulphonic acid sodium salt is obtained.
Potassium cetylate may similarly be reacted with anhydrous dichlor propane potassium sulphonate. That is, likewise, using molecular quantities of the reactants, a solution of about twenty-four parts of cetyl alcohol dissolved in about seventy-five or more parts of toluene is refluxed with about six parts of powdered potassamide until no further ammonia is evolved. About twenty-three parts of anhydrous 2, 3 dichlor propane potassium sulphonate are added to the alkaline solution and the mixture refluxed for about twelve hours while vigorously stirring.
-The toluene is removed by vacuum distillation and the residue is taken up with water and extracted with butyl alcohol to remove the active ingredient from the potassium chloride. Upon evaporation of the butyl alcohol, a monocetyl It is preferred to pre- 4 ether of beta chlor propane sulphonic acid potassium salt is obtained.
The aliphatic alcohols or alcoholates may be straight or branched chain, saturated or unsaturated, and may be of primary, secondary or tertiary alcohols. Furthermore, they may be of monoor poly-hydroxy substances. The suitable substances include the following alcohols or alcoholates thereof; myristyl alcohol, carnaubyl alcohol, octadecyl alcohol, oleyl alcohol, myricyl alcohol, tertiary amyl alcohol, abietyl alcohol, polyglycol, benzyl alcohol, cyclohexanol, and mixtures thereof. Mixed alcoholates, such as those of alcohols produced by reduction of the coconut oil fatty acids, may be used.
The halogen alkyl sulphonates can be monoor poly-hydroxy and/or halogen substituted, which thus permits the preparation of polyethers. By the term polyis meant two or more. The free sulphonic acids can be prepared by treating the compound with a dilute mineral acid. The free sulphonic acids'are useful for operating in an acid solution, 'such as in metal pickling.
,The halogen and/or hydroxy sulphonate ethers are extremely stable in both alkaline and acid solutions. They are excellent detergents and emulsifiers and find use as domestic cleaning compositions, degreasing compounds, hard water detergents, etc. The presence of the halogen or hydroxy group materially increases the solubility and eflicacy of the compound.
Although the new materials possess unusual deterging, sudsing and water-softening properties by themselves, they may be used with other emulsifying agents, including soaps, rosinates, long chain alcohol sulphates, alkylated aromatic sulphonic acid salts, sulphonated mineral oil extracts, Turkey red oil, lecithin, glycerolamines, monoethanolamine, diethanolamine and trieethanolamine; coloring matter, such as dyes, lakes and pigments; abrasives and inert fillers, such as silica, pumice, feldspar, precipitated chalk,
ethylene, trichlorethylene, glycerine, ethyl alcohol, tetrahydrofurfuryl alcohol, phenol, cyclohexanol, water, tetralin, hexalin, pine oil, mineral oil, mineral oil extracts and naphtha; perfumes and deodorants; fats, oils, fatty acids, monoglycerides, waxes, gums, or resins; germicides, such as phenol mercury chloride, phenyl mercury nitrate, phenyl mercury chloride, methyl salicylate and mercuric chloride; styptics; any of the common water-soluble salts, such as sodium carbonate, borate, phosphate (ortho-, pyro-, hexameta-), hypochlorite, thiosulphate, hydrosulphite, and hyposulphate, or the corresponding ammonium and potassium salts thereof. The type of addition agent to'be used, of course, will depend on the ultimate use of the new composition.
The final detergent composition, with or without one or more addition agents, may be formed into beads, flakes, bars, chips, crystals, powders,
softeners; deodorants and disinfectants; water paints and polishes; sizes, glues and adhesives, such as shellac and casein compositions; liquid solid and paste tooth and mouth detergents, laundry detergents and other textile agents, in-
cluding laundry blueing, bleaching, dyeing and discharging compositions; depilatories; dust preventing compositions; fire extinguishing compositions; drain, lavatory and radiator cleaners; anti-freezing, anti-fogging, and anti-corrosion compositions; wood impregnants; electrolytic baths; etching compositions; cosmetics, shaving preparations; shampoos and hair wave lotions; fat-liquors for leather; photographic solutions; plasticizers; paint, stain and grease removers; dry cleaning compositions; rug cleaners; petroleum de-emulsiiying compositions; fruit washing; and any compositions requiring Wetting, washing, emulsifying, penetrating, solubilizing, dispersing and like agents.
As many apparently widely different embodiments or this invention may be made without departing from the spirit and scope thereof, it is to be understood that the applicant does not limit himself to the specific proportions or em bodiments thereof except as defined in the appended claims.
This application is a continuation in part of applicant's copending application Serial No. 372,916, filed January 2, 1941.
I claim:
1. The process which comprises reacting, in an alkaline condition, a polyhalogen alkyl sulphonate with an aliphatic alcohol compound of the group consisting of alcoholates and alcohols.
2. The process which comprises reacting, in an alkaline condition, a polyhalogen alkyl sulphonate having not more than six carbon atoms with an aliphatic alcoholic compound having at least six carbon atoms of the group consisting of alcoholates and alcohols.
3. The process which comprises reacting, in an alkaline condition, a polyhalogen alkyl sulphonate with a lauryl alcohol compound of the group consisting of alcoholates and alcohols.
4. The process which comprises reacting, under substantially anhydrous alkaline conditions, a polyhalogen alkyl sulphonate having not more than six carbon atoms with an aliphatic alco holate having at least six carbon atoms.
5. The process which comprises reacting, under substantially anhydrous alkaline conditions, a 2,3 (ii-halogen propane sulphonate salt with a long chain aliphatic alcoholate having at least six carbon atoms, to yield a long chain ether of a halogen substituted propane sulphonate salt.
6. The process which comprises reacting, under substantially anhydrous alkaline conditions, a 2,3 di-chlorpropan sulphonate salt with a long chain aliphatic alcoholate having at least six carbon atoms, to yield a long chain ether of a chlorpropane sulphonate salt.
7. The process which comprises reacting, under substantially anhydrous alkaline conditions, a 2,3 di-chlorpropane sulphonate salt with an alcoholate of lauryl alcohol, to yield a lauryl ether of a chlorpropane sulphonate salt.
8. A stable, surface-active, sulphonate of the formula wherein R. is an aliphatic hydrocarbon radical having at least six carbon atoms, Z is oxygen, X is an aliphatic radical substituted by at least one halogen group, Y is a cation, and m and n are small whole numbers.
9. A lauryl ether of a chlorpropane sulphonate salt.
10. A cetyl ether of a chlorpropane sulphonate salt.
11. The process which comprises reacting, in an alkaline condition, a polyhalogen alkyl sulphonate with a cetyl alcohol compound of the group consisting of alcoholates and alcohols.
12. The process which comprises reacting, under substantially anhydrous alkaline conditions, a 2,3 di-chlorpropane sulphonate salt with an alcoholate of cetyl alcohol, to yield a cetyl ether of a chlorpropane sulphonate salt.
RALPH CARLISLE SMITH.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,948,667 Kranzlein Feb. 27, 1934 1,985,747 Steindorfi Dec. 25, 1934 2,094,489 Hueter Sept. 28, 1937 2,029,073 Huttenlocker Jan. 28, 1936 2,062,957 Baldwin Dec. 1, 1936 2,062,958 Baldwin Dec. 1, 1936 FOREIGN PATENTS Number Country Date 421,527 Great Britain Sept. 19, 1933 514,053 Great Britain Oct. 30, 1939
US579315A 1945-02-22 1945-02-22 Ether sulphonates and their production Expired - Lifetime US2427576A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2987569A (en) * 1954-10-12 1961-06-06 Us Electric Mfg Corp Wafer-type cells for dry batteries and method for making same
US3245914A (en) * 1959-09-28 1966-04-12 Dow Chemical Co Germicidal alkylhalodiphenyl oxide sulfonate compositions

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1948667A (en) * 1924-02-07 1934-02-27 Ig Farbenindustrie Ag Phenol ethers and process of preparing them
GB421527A (en) * 1933-03-20 1934-12-17 Deutsche Hydrierwerke Ag Improvements in and relating to the manufacture and use of substances suitable for use as wetting-out, washing, cleansing, frothing and dispersing agents
US1985747A (en) * 1934-12-25 Ether-like constituted compound
US2029073A (en) * 1932-04-18 1936-01-28 Huttenlocher Richard Production of sulphonic acids
US2062957A (en) * 1931-05-16 1936-12-01 Ici Ltd Process of preparing aliphatic sulpho-ethers
US2094489A (en) * 1937-09-28 Wetting-out
GB514053A (en) * 1938-01-18 1939-10-30

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1985747A (en) * 1934-12-25 Ether-like constituted compound
US2094489A (en) * 1937-09-28 Wetting-out
US1948667A (en) * 1924-02-07 1934-02-27 Ig Farbenindustrie Ag Phenol ethers and process of preparing them
US2062957A (en) * 1931-05-16 1936-12-01 Ici Ltd Process of preparing aliphatic sulpho-ethers
US2062958A (en) * 1931-05-16 1936-12-01 Ether compounds
US2029073A (en) * 1932-04-18 1936-01-28 Huttenlocher Richard Production of sulphonic acids
GB421527A (en) * 1933-03-20 1934-12-17 Deutsche Hydrierwerke Ag Improvements in and relating to the manufacture and use of substances suitable for use as wetting-out, washing, cleansing, frothing and dispersing agents
GB514053A (en) * 1938-01-18 1939-10-30

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2987569A (en) * 1954-10-12 1961-06-06 Us Electric Mfg Corp Wafer-type cells for dry batteries and method for making same
US3245914A (en) * 1959-09-28 1966-04-12 Dow Chemical Co Germicidal alkylhalodiphenyl oxide sulfonate compositions

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