US3413221A - Wash agents - Google Patents

Wash agents Download PDF

Info

Publication number
US3413221A
US3413221A US568677A US56867766A US3413221A US 3413221 A US3413221 A US 3413221A US 568677 A US568677 A US 568677A US 56867766 A US56867766 A US 56867766A US 3413221 A US3413221 A US 3413221A
Authority
US
United States
Prior art keywords
wash
weight percent
sulfonated
agent
acid
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
Application number
US568677A
Other languages
English (en)
Inventor
Gotte Ernst
Stein Werner
Weiss Herbert
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Application granted granted Critical
Publication of US3413221A publication Critical patent/US3413221A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • 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
    • C11D1/37—Mixtures of compounds all of which are anionic
    • 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
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • 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
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • 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
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides

Definitions

  • This invention relates to improved wash agent compositions, and more particularly it relates to improved wash agent compositions comprising synergistic mixtures of sulfonated salts of saturated fatty acid esters, sulfated fatty alcohols and/or alkyl benzene sulfonates.
  • Dialkyl salts of sulfonated fatty acids alone and 1n combination with alkali alkylbenzene sulfonates and/or alkali salts of sulfated fatty alcohols have already been evaluated with respect to their effectiveness as wash agents.
  • the salts of sulfonated fatty acids alone, the salts of alkyl benzene sulfonates, and the salts of the fatty acids alone have been found not to be entirely satisfactory due to their limited solubility at operating temperatures, the ultimate expense to the consumer, their effectiveness as dirt removal agents, etc.
  • the mixture has been found to be characterized by synergism.
  • One of the objects of the invention is the provision of a novel washing agent composition of the type indicated possessing superior properties, making it especially advantageous for use in various laundry applications.
  • Another object of the invention is the provision of wash-agent compositions which are adapted for use either as fine or boiling wash-agents and which are superior to the wash-agents of the same general type now available.
  • Another object of the invention is to provide improved wash-agent compositions based on mixtures of sulfonated salts of saturated fatty acid esters, sulfated fatty alcohol and/ or alkyl benzene sulfonates.
  • wash-agents having superior properties are obtained by combining a sulfonated salt of a saturated fatty acid ester with a sulfated fatty alcohol and/or an alkyl benzene sulfonate.
  • alkyl benzene sulfonates in accordance with the invention are preferably selected so that the alkyl radical contains chain branchings, as a result of which the same are much more slowly decomposed by bacteria in the birth-Lite;
  • alkyl benzene sulfonates characterized by straight alkyl chains.
  • the alkyl benzene sulfonates are generally produced by polymerizing propylene, condensing a polypropylene with benzene to obtain the alkyl benzene, and thereafter sulfonating the alkyl benzene.
  • the polypropylene benzene sulfonates having 9-15 carbon atoms in the alkyl radical and in particular having 12 carbon atoms in the alkyl radical have proved especially effective.
  • alkyl benzene molecules present in an isomeric mixture possess 12 carbon atoms in'the alkyl radical, and these alkyl benzene sulfonates have come to be called by the term tetrapropylene benzene sulfonate.
  • alkyl benzene sulfonates the alkyl component of which exhibits other branchings or alkyl benzene sulfonates the alkyl component of which is of an unbranched nature-i.e., straight chainmay also be satisfactorily used in the compositions of the invention.
  • the sulfated fatty alcohols used in the present invention are obtainable from saturated or unsaturated, and preferably straight chain fatty alcohols, having l020 and preferably 12-18 carbon atoms in their molecule.
  • the sulfonated fatty acid ester salts for use in the compositions of the invention are obtained in the known manner, either by the introduction of the sulfonic acid group into the fatty acid radical, followed by esterification of the carboxylic group by means of a monovalent alcohol, or, alternatively, by introducing the sulfonic acid radical into an ester obtained by esterifying a fatty acid by means of a monovalent alcohol.
  • esters of sulfonic fatty acids The fatty acids which may be.used are preferably saturated straight chain fatty acids having l0-20, and preferably 12-18, carbon atoms, and the alcohol radical is preferably derived from a monovalent straight chain saturated aliphatic alcohol having 1-10 carbon atoms in its molecule.
  • the starting fatty acid and alcohol are selected with a view that the ester product produced contains at least 11 and, at most, 22 carbon atoms, preferably 13-20 carbon atoms.
  • esters falling within the aforesaid definition are all water-soluble but to different degrees; their solubility decreasing with an increase in the number of carbon atoms present in the molecule.
  • washing and the foaming properties of the sulfonated ester salt are dependent on the molecular size.
  • the general statement may be made that the more readily soluble compounds, i.e., those having a smaller number of carbon atoms, are characterized by a better foaming capacity, while the other ester salts having the larger number of carbon atoms are capable of effecting a better washing.
  • the washing and foaming capabilities of the sulfonated ester salts in addition are dependent on the structure of the compound, and specifically the combination of fatty acid and fatty alcohol employed in the esterification, the other materials which are present in the washing medium and, for example, those contributing to the hardness or softness of the water as well as on the temperature of the washing medium. While the more readily soluble sulfonated ester salts are equally suitable for use at room temperature or at slightly increased temperatures as, for example, up to about 50 C., the less readily soluble sulfonated ester salts are advantageously used only at higher temperatures of about S0-l00 C. It is, therefore, advisable in selecting a sulfonated ester salt salt for the combination to suit the compound selected for its intended use.
  • the sulfonated ester salts of fatty acids having 12-14 carbon atoms and alcohols having 1-4 carbon atoms have been found to be particularly good foam-producing agents while'the sulfonated ester salts of fatty acids having 16- 18 carbon atoms and alcohols having 1-4 carbon atoms, the total number of carbon atoms present in the ester molecule not exceeding 20, demonstrate especially good washing properties.
  • the fatty acids are generally of natural origin and, in the production of the sulfonated ester salt, the starting fat material is selected on the basis that its fatty acid composition will come closest to that which is required for producing the desired properties in the final sulfonated salt ester.
  • the fat starting materials which are selected are those whose fatty acid components in the main consist of fatty acids having 12-14 carbon atoms.
  • This fat starting material includes the so-called lauric acid fats" by which is intended the group of fats so termed and further defined in A. E. Bailey: Industrial Oil and Fat Products, New York, 1951, page 121. The most important fats and those of greatest practical significance coming within this definition are enumerated by Bailey at pages 133-138 of the aforesaid publication.
  • the other natural fats and/or their hydrogenation products which preferably contain 16-18 carbon atoms. It has been found that the esters of hydrogenated tallow fatty acids are particularly favorable starting materials in this connection.
  • the combinations are optimally effective when the sulfonated ester component is present in an amount of from 20-90 weight percent of the total synthetic wash-active material, the alkyl benzene sulfonate and/or sulfated fatty alcohol constituting the remainder.
  • the alkyl benzene sulfonate and sulfated fatty alcohol may be present in any desired mixing ratio.
  • the sulfonated ester salt is present in an amount of from 35-70 weight percent referred to the combination washing agent.
  • the composition producing optimal effect as regards washing capacity for a specific combination of wash-active substances is also capable of producing the optimal foaming capacity.
  • Such combinations are then advantageously employed in the production of a foaming wash-agent.
  • the foaming quality of such agents may be further improved through the addition of any of the known foaming stabilizers to the composition.
  • the optimal ranges for superior washing and foaming qualities do not coincide and in such instances as, for example, in the cases of agents characterized by good washing and mediocre to poor foaming properties, the combinations are suitable for the production of low foaming preparations and are particularly advantageously used in washing machines.
  • the foaming property of the waste water remaining after the washing treatment is therefore not only diminished in that the concentration of the total wash-active substances becomes less with the exhaustion of the sulfonated ester salt but also in that the combination is taken out of the range of optimal composition for improved foaming capacity by the destruction of the sulfonated ester salt which has taken place.
  • wash-agent combinations in accordance with the invention are suitable for use per se or in admixture with the conventional products employed in the formulation of wash-agents for use in the washing and bleaching treatment of textiles, and which impart to the preparation.
  • a pH value within the range of 6-12. The pH value is determined using as the test sample a 1% solution of a wash-agent.
  • the pH range extending from 6-12 includes the agents intended as fine wash-agents and which are required to be regulated so as to have a slightly acid to alkaline pHi.e., approximately within the range of 68.5, and preferably within the range of 7-8, as well as the agents intended for use as boiling wash-agents and having a pH value approximately within the range of 9-12 and preferably of from 9.5-1L5.
  • wash-agents in accordance with the invention may be employed in conjunction with neutral or alkaline reacting salts, slightly acid reacting compounds, as well as the customary agents used to improve foaming, soil removal, and such additives as bleaching agents, corrosion protection agents, etc.
  • a neutral reacting salt which is most advantageously used is sodium sulfate, the same additionally acting to improve the effectiveness of the combination in accordance with the invention.
  • wash-alkalies which are suitable for use in connection with the invention include the alkali carbonates, alkali-bicarbonates, water-soluble alkali silicates, alkaliorthophosphates, etc.
  • the combination wash-agent in accordance with the invention may be used to particular advantage in conjunction with the anhydrous phosphates.
  • the anhydrous phosphates employed may be any polyphosphate, such as, a pyrophosphate or metaphosphate, the tripolyphosphates and tetrapolyphosphates having been found to possess particular practical significance.
  • the pyroand polyphosphates are alkaline in reaction and are therefore able, when used alone in boiling wash-agents, to impart to the same the necessary alkalinity.
  • the metaphosphates produce a slightly acid reaction and are therefore advantageously utilized in the production of fine wash-agents serving to decrease the pH value of the resulting combination.
  • phosphates suitable for the same purpose include the acid orthophosphates and the acid pyrophosphates.
  • Weak inorganic or organic acids or acid salts of strong inorganic acids, such as, for example, boric acid, citric acid, oxalic acid, lactic acid, glycolic acid, tartaric acid, and amido-sulfonic acid, are instances of other materials suitable for use in regulating the pH value of the washing agent.
  • the preparation in accordance with the invention may be used in combination with the other ordinary substances as are used in wash-agents.
  • These substances include inorganic or organic active oxygen carriers, as, for example, the percompounds and, in particular, sodium perborate.
  • Products functioning to improve the soil removal property and foaming qualities of the combination wash-agent are additionally included in the preparation of the wash-agent.
  • Instances of substances serving to improve the soil removal capacity of the wash-agent include water-soluble colloids, and preferably those of an organic nature, as, for example, the water-soluble salts of polymeric carbon acids, sizes, gelatin, salts of ether carbon acids or ether sulfonic acids of starch or cellulose, or salts of acid sulfuric acid esters of cellulose or starch.
  • Additives for improving the foaming capacity of the wash-agent combination of the invention include fatty acid amides which may be substituted at the nitrogen atom with alkylor alkylol-radicals having at most 6 carbon atoms per radical, as well as the addition products of ethylene oxide to these unsubstituted or substituted fatty acid amides.
  • the salts which may be added to the wash-agents in accordance with the invention may be derived from inorganic or organic alkalies as, for example, from sodium, potassium or fiom the easily soluble organic amines.
  • Such salts include alkylol amines, for example, mono, di, or triethanolamine.
  • the easily soluble salts which may be used in conjunction with the wash-agent combination of the invention include wash-active organic sulfates or sulfonates, such additions being particularly valuable in the production of the wash-agents to be used in paste or liquid form.
  • wash-agent preparations so that, in s;ite of the high concentration of active material, they do not form precipitates readily.
  • anions which are already present in the wash-agent, although similar thought has to be given to the anionic wash-active additives as they are advantageously added in the form of their readily soluble salts with inorganic or organic cations. It is, therefore, advisable to provide, in many instances, for the presence of various cations in the washing combination, paving the way for satisfactory further additions.
  • water-soluble organic solvents which are particularly suitable are those having boiling points above 100 C., such as, for example, the ethers or polyethers of polyvalent alcohols and the partial ethers of polyvalent and monovalent alcohols.
  • suitable solvents include tri-, tetraor polyethyleneglycol, polyglycerins, the partial ethers of ethyleneglycol, propyleneglycol, glycerin, and aliphatic monovalent alcohols having 1-4 carbon atoms.
  • wash-agents in accordance with the invention, as has already been noted, are suitable for use alone or in combination with various additives, instances of which have been set forth. Additionally, the agents or the compositions containing the same as active ingredients, can be employed in the solid form (powder or lumps), as pastes or creams or in the form of their solutions.
  • wash-agents agents in which the wash-active substance was only present in combination with sodium sulfate, in order that the effect of the wash-active substance as far as possible be unaffected by the effect of any of the other possible washagent additions.
  • wash-agent there is intended the technical more or less pure wash-active substance combinations which, as a result of their manufacture, still contain slight amounts of sodium sulfate as well as the products which have been processed to completion, as, for example, by addition thereto of the conventional wash-agent additions and which qualify as fine or boiling wash-agents.
  • sodium sulfate may be present in large quantities since the same consists in the effect of the wash-active substance or substances.
  • the washing effect of the fine wash-agent can be increased by replacing the sodium sulfate by magnesium sulfate and particularly if the magnesium sulfate which is added is not brought into precipitation by the other wash-agent components.
  • wash-agents in accordance with the invention have approximately the following composition:
  • an active oxygen material present as any of the conventional active oxygen carriers as, for example, a percompound
  • wash-active combinations of the invention may be used in other concentrations and proportions than are indicated in the examples and that it is not intended to limit the invention to those values as set out in the examples.
  • the wash-active combinations of the invention may be used in other concentrations and proportions than are indicated in the examples and that it is not intended to limit the invention to those values as set out in the examples.
  • the wash-active combinations of the invention may be used in other concentrations and proportions than are indicated in the examples and that it is not intended to limit the invention to those values as set out in the examples.
  • the wash-active combinations of the invention may be used in other concentrations and proportions than are indicated in the examples and that it is not intended to limit the invention to those values as set out in the examples.
  • the wash-active combinations of the invention may be used in other concentrations and proportions than are indicated in the examples and that it is not intended to limit the invention to those values as set out in the examples.
  • range of concentration of the wash-active combination lies beween 0.3- g./l. and most preferably within the range of 0.5-2 g./l.
  • Example 2 A wash-agent of the type as set out in Example 1 and under the working conditions therein indicated is utilized with good or optimal washing capacity it the sulfonated palmitic acid ethyl ester salt is replaced by the following sulfonated ester salts:
  • wash-agent 1.5 g./l. of wash-agent in water having a 10 German hardness and a temperature of 40 C. Good or optimal. washing and foaming capacity:
  • Example 9 The foaming properties of two wash-agents having the following general composition were determined according to the procedure hereinafter set out:
  • the remainder consisting of sodium sulfate and water.
  • washing medium a bath having a concentration of 4 g./l. of wash-agent in water having 16 German hardness and which had been heated to a temperature of 90 C.
  • 4 liters of the washing medium which had been used in the run were removed following completion of the washing.
  • the used washing medium withdrawn at a temperature of 80, 60, 40, and 25 C., respectively, was permitted to flow from a vessel having an outlet of 3.25 mm. clear width within 4 minutes from a height of 80 cm. into a cylindrical vessel having a diameter of 21.5 cm.
  • the quantity of foam which was formed as a result in the collecting vessel was measured immediately, and at subsequent intervals of 1, 3, 4, 5, and 10 minutes and the heights of the foam recorded in each instance added together.
  • the sum thereby obtained constitutes a good gauge for the foaming properties of the solution being measured under conditions closely paralleling those in actual practice. It takes into consideration the initial foaming capacity as well as the foam stability.
  • the latter washing agent was superior in the foaming properties observed to the agent which contained only the tetrapropylene benzene sulfate.
  • Alkyl benzene sulfonates thus produced are characterized by a content of compounds having 12 and 13 carbon atoms in the alkyl radical of more than 50%. 70 weight percent sodium sulfate.
  • a washzagent consisting essentially of:
  • a sulfonated fatty acid ester salt constituting the salt of an'ester of a saturated fatty acid having from 10-20 carbon atoms and a saturated monovalent aliphatic alcohol having 1-10 carbon atoms, c0ntain ing the sulfonic acid group in the fatty acid radical and having the formula SOs wherein R-CH-COO designates the fatty radical and R the monovalent aliphatic alcohol radical, and
  • a wash agent according to claim 1 additionally containing sodium sulfate up to 80 percent of the total mixture.
  • a wash agent according to claim 1 the 1 percent aqueous solution of which has a pH of 6-12.
  • a wash agent according to claim 1 having improved foaming properties in which said sulfonated fatty acid ester salt constitutes the salt of an ester of a saturated fatty acid having from 12-14 carbon atoms and a saturated monovalent aliphatic alcohol having 1-4 carbon atoms.
  • a wash agent according to claim 1 having improved washing properties and a low foaming capacity in which said sulfonated fatty acid ester salt constitutes the salt of an ester of a saturated fatty acid having from 16- 18 carbon atoms and a saturated monovalent aliphatic alcohol having l-4 carbon atoms.
  • a wash agent according to claim 1 containing 33 weight percent of a mixture of tetrapropylene benzene sulfonate and a sulfonated palmitic acid ethyl ester salt', and
  • a wash according to claim 1 containing 30 weight percent of a mixture of a sulfated cur-C fatty alcohol and a sulfonated palmitic acid butyl ester salt;
  • a wash agent according to claim 1 containing 30 weight percent of a mixture of tetrapropylene benzene sulfonate, a sulfated C -C fatty alcohol, and a sulfonated ester salt of palmitic acid butyl ester;
  • a wash agent according to claim 1 in the form of a mixture in which said first and second components together constitute (a) -75 weight percent thereof with 12 the remainder of (b) 25-95 weight percent being composed of (i) 0-20 weight percent of a foam improving agent selected from the group consisting of fatty acid amides and their addition products with ethylene oxide,
  • wash alkali selected from the group consisting of alkali metal carbonates, alkali metal bicarbonates, and alkali metal silicates
  • a soil removing agent selected from the group consisting of water-soluble sizes, gelatin, salts of ether carboxylic acids of cellulose, salts of ether carboxylic acids of starch, salts of ether sulfonic acids of cellulose, salts of ether sulfonic acids of starch, salts of acid sulfuric acid esters of cellulose and salts of acid sulfuric acid esters of starch.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Detergent Compositions (AREA)
US568677A 1961-03-01 1966-07-28 Wash agents Expired - Lifetime US3413221A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEH41884A DE1155556B (de) 1961-03-01 1961-03-01 Waschmittel
DE1962H0045759 DE1170573C2 (de) 1961-03-01 1962-05-11 Waschmittel

Publications (1)

Publication Number Publication Date
US3413221A true US3413221A (en) 1968-11-26

Family

ID=25979734

Family Applications (1)

Application Number Title Priority Date Filing Date
US568677A Expired - Lifetime US3413221A (en) 1961-03-01 1966-07-28 Wash agents

Country Status (6)

Country Link
US (1) US3413221A (en。)
BE (2) BE614508A (en。)
CH (2) CH417827A (en。)
DE (2) DE1155556B (en。)
GB (2) GB980543A (en。)
NL (3) NL275383A (en。)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3516835A (en) * 1965-10-29 1970-06-23 Gaf Corp Coating compositions comprising alpha-sulfo lower alkyl ester of a c7 to c18 fatty acid
JPS4963703A (en。) * 1972-10-23 1974-06-20
JPS4971003A (en。) * 1972-11-06 1974-07-09
JPS5228507A (en) * 1975-08-29 1977-03-03 Nippon Oil & Fats Co Ltd Detergent composition
US4131558A (en) * 1975-02-14 1978-12-26 The Procter & Gamble Company Process for preparing an orthophosphate-silicate detergent product
US4416809A (en) * 1981-04-30 1983-11-22 Lion Corporation Granular detergent composition
US4495092A (en) * 1983-02-17 1985-01-22 Henkel Kommanditgesellschaft Auf Aktien Viscosity regulators for high-viscosity surfactant concentrates
US4532076A (en) * 1982-02-11 1985-07-30 Henkel Kommanditgesellschaft Auf Aktien Aqueous anionic surfactant concentrates containing viscosity reducing agents
US5454982A (en) * 1990-09-28 1995-10-03 The Procter & Gamble Company Detergent composition containing polyhydroxy fatty acid amide and alkyl ester sulfonate surfactants
WO2016160407A1 (en) * 2015-03-31 2016-10-06 Stepan Company Detergents based on alpha-sulfonated fatty ester surfactants
CN113481066A (zh) * 2021-07-02 2021-10-08 广东博科新材料有限公司 一种除油剂及其制备方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2260619B1 (en。) * 1974-02-08 1977-03-04 Armag
LU71583A1 (en。) 1975-01-02 1976-11-11 Procter & Gamble Europ
JPS59206495A (ja) * 1983-05-10 1984-11-22 ライオン株式会社 混合界面活性剤組成物

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2043476A (en) * 1936-06-09 Cabboxylates of aliphatic alcohols
US2303212A (en) * 1939-05-26 1942-11-24 Solvay Process Co Soap composition
US2460968A (en) * 1943-09-28 1949-02-08 Innovations Chimiques Sinnova Method for the obtainment of aliphatic sulfonic acids and esters thereof
US2806044A (en) * 1955-01-14 1957-09-10 James K Weil Esters of hydroxyalkanesulfonates with alpha-sulfonated long-chain fatty acids
US2876200A (en) * 1955-04-08 1959-03-03 Procter & Gamble Making perborate containing detergents
US2972583A (en) * 1956-05-17 1961-02-21 Colgate Palmolive Co Detergent cake and method of making same
US3338838A (en) * 1964-11-17 1967-08-29 Procter & Gamble Detergent composition

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2915473A (en) * 1956-04-17 1959-12-01 Alexander J Stirton Detergent compositions

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2043476A (en) * 1936-06-09 Cabboxylates of aliphatic alcohols
US2303212A (en) * 1939-05-26 1942-11-24 Solvay Process Co Soap composition
US2460968A (en) * 1943-09-28 1949-02-08 Innovations Chimiques Sinnova Method for the obtainment of aliphatic sulfonic acids and esters thereof
US2806044A (en) * 1955-01-14 1957-09-10 James K Weil Esters of hydroxyalkanesulfonates with alpha-sulfonated long-chain fatty acids
US2876200A (en) * 1955-04-08 1959-03-03 Procter & Gamble Making perborate containing detergents
US2972583A (en) * 1956-05-17 1961-02-21 Colgate Palmolive Co Detergent cake and method of making same
US3338838A (en) * 1964-11-17 1967-08-29 Procter & Gamble Detergent composition

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3516835A (en) * 1965-10-29 1970-06-23 Gaf Corp Coating compositions comprising alpha-sulfo lower alkyl ester of a c7 to c18 fatty acid
JPS4963703A (en。) * 1972-10-23 1974-06-20
JPS4971003A (en。) * 1972-11-06 1974-07-09
US4131558A (en) * 1975-02-14 1978-12-26 The Procter & Gamble Company Process for preparing an orthophosphate-silicate detergent product
JPS5228507A (en) * 1975-08-29 1977-03-03 Nippon Oil & Fats Co Ltd Detergent composition
US4416809A (en) * 1981-04-30 1983-11-22 Lion Corporation Granular detergent composition
US4532076A (en) * 1982-02-11 1985-07-30 Henkel Kommanditgesellschaft Auf Aktien Aqueous anionic surfactant concentrates containing viscosity reducing agents
US4495092A (en) * 1983-02-17 1985-01-22 Henkel Kommanditgesellschaft Auf Aktien Viscosity regulators for high-viscosity surfactant concentrates
US5454982A (en) * 1990-09-28 1995-10-03 The Procter & Gamble Company Detergent composition containing polyhydroxy fatty acid amide and alkyl ester sulfonate surfactants
WO2016160407A1 (en) * 2015-03-31 2016-10-06 Stepan Company Detergents based on alpha-sulfonated fatty ester surfactants
CN113481066A (zh) * 2021-07-02 2021-10-08 广东博科新材料有限公司 一种除油剂及其制备方法

Also Published As

Publication number Publication date
CH417827A (de) 1966-07-31
NL292581A (en。)
NL275383A (en。)
DE1155556B (de) 1963-10-10
BE614508A (en。)
GB1022663A (en) 1966-03-16
DE1170573C2 (de) 1973-07-19
NL136748C (en。)
DE1170573B (de) 1964-05-21
BE632155A (en。)
GB980543A (en) 1965-01-13
CH455113A (de) 1968-04-30

Similar Documents

Publication Publication Date Title
US2486922A (en) Stabilized detergent composition
US3413221A (en) Wash agents
US2486921A (en) Detergent composition
US2787595A (en) Sulfoxide containing detergent compositions
US3686098A (en) Novel detergent composition
US2141189A (en) Bleaching and cleansing compositions
US3951879A (en) Detergent that reduces electrostatic cling of synthetic fabrics
JPH0347679B2 (en。)
US3285856A (en) Low foaming compositions having good detersive properties
US2527076A (en) Detergent composition
US2152520A (en) Bleaching, washing, cleansing, and rinsing agents
DE2355983A1 (de) Granulierte spruehgetrocknete waschund reinigungsmittel
US4248729A (en) Detergency booster
US2365215A (en) Detergent composition
US3231508A (en) Low foaming detergent compositions
US4198308A (en) Manufacture of free-flowing fabric softening detergent
US2944028A (en) Sulfonate detergent compositions
US2746931A (en) Synthetic detergent compositions
US3011977A (en) Detergent composition
US2915473A (en) Detergent compositions
US3067144A (en) Detergent composition
US2376096A (en) Detergent composition
US3390096A (en) Combinations of wash-active substances in liquid or paste form
US4832863A (en) Low-foam phosphate-free detergent
US3345301A (en) Pourable and free-flowing detergent, wetting, and emulsifying compositions