US3901832A - Detergent cake containing monoalkylsulfosuccinate and preparation - Google Patents

Detergent cake containing monoalkylsulfosuccinate and preparation Download PDF

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Publication number
US3901832A
US3901832A US296414A US29641472A US3901832A US 3901832 A US3901832 A US 3901832A US 296414 A US296414 A US 296414A US 29641472 A US29641472 A US 29641472A US 3901832 A US3901832 A US 3901832A
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United States
Prior art keywords
plasticizer
monoalkylsulfosuccinate
carbon atoms
weight
group
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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US296414A
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English (en)
Inventor
Bernard Baron Dugan
Coenraad Jacobus Beuke Scholtz
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.)
Colgate Palmolive Co
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Colgate Palmolive Co
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Filing date
Publication date
Priority to CA798803A priority Critical patent/CA798803A/en
Priority to DE19661617052 priority patent/DE1617052A1/de
Priority to CH1180166A priority patent/CH488802A/de
Priority to SE11102/66A priority patent/SE343595B/xx
Priority to AT07759/66A priority patent/AT279009B/de
Priority to FR73238A priority patent/FR1489582A/fr
Priority to GB37066/66A priority patent/GB1153303A/en
Priority to BE685663D priority patent/BE685663A/xx
Priority to NL6611798A priority patent/NL6611798A/xx
Priority to DK433766A priority patent/DK133054C/da
Application filed by Colgate Palmolive Co filed Critical Colgate Palmolive Co
Priority to US296414A priority patent/US3901832A/en
Application granted granted Critical
Publication of US3901832A publication Critical patent/US3901832A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • 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
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0047—Detergents in the form of bars or tablets
    • C11D17/006—Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates

Definitions

  • ABSTRACT A process for the production of detergent cakes containing a monoalkylsulfosuccinate and a plasticizer in which a monoaklyl ester of a betenedioic acid is reacted with a sul-fite in the presence of a plasticizer in the liquid state and the article formed thereby.
  • This invention relates to cleansing bars containinga sulfosuccinate detergent, and, more particularly, the invention is concerned with a process for the'production of detergent cakes containing a monoalkyl sulfosuccinate and suitable for use as cleansing bars, and to the detergent cakes per se.
  • the process of this invention enables the production of superior cakes in a simple, economical, and facile manner whereby such detergent cakes may be formed in the equipment normally used and present in any soap making operation, even those operations where modern processing equipment is not available. Accordingly, the capital equipment cost for converting in accordance with this invention a soap bar'production facility to a detergent bar production facility is negligible or nonexistent.
  • the raw materials required for the production of detergent cakes by the process of this invention are readily available and inexpensive.
  • the detergent cakes formed by the process of this invention are of an exceptionally high quality, and provide a quick and desirable amount of foam.
  • the detergent cake both wet and dry has substantially the same tactile characteristics and density as a normalsoap bar, and the detergent cake, when used in a body of hard water,- results in a complete absence of any objectionable adherent scum or curd such as that which clings to the sides of a bathtub and forms a ring thereon, but the detergent confers a translucence to water of the type formed by soap thereby making it readily evident that the water has been used.
  • the detergent cakes of this invention can be free or substantially free from inorganic salts and therefore do not feel gritty and are devoid of undesirable efflorescene. I
  • a solid detergen bar is formed by a process including the steps of reacting a monoalkyl ester of butenedioic acid with a sulphite at an elevated temperature and in the presence of a molten plasticizer of the type specificallyset forth hereinbelow, cooling the mass to thereby form a prod uct containing a substantially neutral water soluble salt of a sulfosuccinate monoester of the type described in detail hereinbelow in admixture with the plasticizer, and then processing the solid on conventional soap processing equipment thereby to form the product into cake or bar form.
  • the monoalkyl sulfosuccinates useful in the present invention are desirably formed by the reaction of a higher molecular weight alcohol with a .butenedioic acid or anhydride such as maleic anhydride or acid or fumaric acid.
  • the high molecular weight alcohol is preferably lauryl alcohol or a mixture of alcohols in which lauryl alcohol predominates.
  • the law ryl alcohol is reacted with maleic anhydride to form the monolaurylester of maleic acid.
  • the lauryl maleate is then reacted with a sulphite such as sodium sulphite to produce disodium lauryl sulfosuccinate.
  • the reaction between the lauryl maleate and the sodium sulphite is preferably carried out with the lauryl maleate dissolved or dispersed in a molten plasticizer such as glyceryl monostearate, although the plasticizer may be added subsequent to the reaction.
  • a molten plasticizer such as glyceryl monostearate
  • the product of the reaction along with the plasticizer is capable of being used as such or with additives such as perfumes, opacifiers,and the like for forming detergent bars.
  • additives such as perfumes, opacifiers,and the like for forming detergent bars.
  • these relatively inexpensive, easily obtainable materials can be reacted in readily available equipment asiunsophistic ated as a kettle, yet form :a highly desirable product.
  • maleic anhydride is simply reacted with a suitablealcohol to provide the ester, the latter is then diluted with the plasticizer and then the 'maleic acid half-ester is reacted with thesulphite to produce the corresponding sulfosuccinate mono ester which'is substituted according to the sulphite used.
  • Qdisodiumalkyl sulfosuccinate is produced when sodium sulphite is used.
  • sodium sulphite there may desirably be used other alkali metal or ammonium sulphites, or alkaline earth metal sulphites, and bisulphites.
  • lauryl alcohol and mixtures of alcohols containing lauryl alcohol are preferred, it is possible to use reactants containing an acyclic radical having 12 carbon atoms and a suitable moiety which will link such acyclic radical to the butenedioic acid, such as for example lauric monoethanolamide or lauric diethanolamide.
  • The'acyclic chain of the said reactant may be comprised solely of twelve carbon atoms, or the reactant used may comprise mixtures in which the size of the acyclic chain varies from 12 to l8 carbon atoms. In such mixtures, however, a predominant portion of the acyclic chains must have twelve carbon atoms. By predominant portion it is meant that at least 20 percent and preferably 50 percent of the acyclic chains contain 12 carbon atoms.
  • the compound used must, however, have a reactive hydroxyl group.
  • the monoalkyl sulfosuccinate (as used herein the term monoalkyl refers to radicals formed from alcohols and hydroxyl bearing equivalents thereof as described" in the paragraph immediately above) should be present in an amount of about 40 to 95 percent by weight of the detergent mass; i.e. before the addition of nonessential'additives such as perfume, color, etc.
  • the half ester is present in van amount of between about 60 and percent by weight.
  • the plasticizing agent which advantageously will also be-used as a reaction medium for the reacting constituents, is desirably awaxy or wax-like material such as a glyceryl mono ester, and is preferably glyceryl monostearate.
  • a glyceryl mono ester such as a glyceryl mono ester
  • glyceryl monostearate a glyceryl monostearate.
  • Any organic compound which is a solid orsemi-solid at ordinary temperatures, which melts at the reaction temperature to provide an oily liquid defining the medium in which the reaction is carried out in place of water, and. which is of the high boiling, nonvolatile type having solubility or dispersibility in water may be used.
  • the plasticizer should be sufficiently hydrophilic to produce an emulsion when the final detergent cake product is used in water.
  • the plasticizing agents that can be used should also be resistant to crys tallization and segregation under the different temperature and aging conditions to which the detergent bar or cake may be subjected during storage and use. These plasticizing substances which are solid or semi-solid and which maintain a more or less definite form at ordinary temperatures are hereinafter referred to as normally solid substances.
  • Organic compounds which function satisfactorily as plasticizing agents and which broaden the plasticity range, as aforementioned, are the high molecular weight fatty acid esters of polyhydric alcohols.
  • long-chain polyhydric alcohol monoand distearates and particularly the ether-alcohol fatty acid esters, i.e. diethylene glycol monoand di-stearates, are especially useful.
  • These compounds are emulsifying agents, and promote the formation of a synthetic detergent bar having a smooth, uniform texture throughout.
  • organic plasticizing agents which may be used are those normally solid glycerol mono esters of coconut fatty acids; ethylene glycol di-stearate, and the diethylene glycol monoand di-esters of palmitic, myristic, oleic, lauric and coconut oil acids as well as the corresponding hydrogenated fatty acids; propylene glycol monoand di-esters of stearic, cleic, laurie, myristic, palmitic, coconut oil fatty acids as well as the corresponding hydrogenated fatty acids, etc., as well as suitable glyceryl and ethylene glycol mono esters of such fatty acids, and the like, which esters are normally solid, and which dissolve in water but at a slow rate.
  • a paraffin wax containing a polar compound which under the conditions of use of the bar will be sufficiently dispersed or emulsified. Mixtures of the various organic compounds may, of course, be employed. Where, however, substances are used which are readily dissolved in water there is a tendency towards the production of a bar which is not as firm and dry to the touch as otherwise, and the finished bar or cake dissolves less slowly in water.
  • a detergent bar which contains a plasticity modifying agent as herein described, may gradually harden upon standing in the air at room temperatures without changing-its other physical properties or its chemical properties. It is preferred, however, to use a product such as glyceryl monostearate which is sufficiently hydrophilic to produce an emulsion when the final product is dissolved in water.
  • a product such as glyceryl monostearate which is sufficiently hydrophilic to produce an emulsion when the final product is dissolved in water.
  • a glyceryl monostearate derived from hydrogenated tallow oil is used, in which instance there is a substantial proportion of palmitic acid rather than one which is derived from hydrogenated ground nut oil which contains almost all stearic acid.
  • a balance should be struck between hydrophilic and emollient properties. For example.
  • glyceryl monostearate is compatible with the production of an excellent foam and and the complete absence of adherent scum and leaves the hands with a dry and rather talc-like feel while tallow alcohol leaves the hands with a slightly more emollient feeling.
  • the tallow alcohol may be treated to form the ethylene oxide adduct thereof.
  • Another desirable plasticizer that may be used in compatible amounts is the ethylene oxide adduct of hydrogenated tallow fatty acids.
  • plasticizer varies depending upon the composition to be plodded and the plasticizing agent employed.
  • amounts of plasticizer of from about 5 to 60 percent by weight of the detergent mass may be utilized to advantage, and amounts of between 20 and 30 percent are highly desirable with an amount of about 25 percent being preferred.
  • Moisture may be present in the final 'product in an amount up to about [0 percent, the upper limit being determined by the desired hardness of the detergent cake. The greater the quantity of moisture, the softer the bar.
  • toilet cake additives may be incorporated into the mass before it sets too hard and before it is shaped into its final bar form.
  • inorganic or organic coloring materials e.g. pigments, dyes, etc.
  • Some coloring materials such as titanium dioxide function both as a coloring agent and as a hardener.
  • the titanium dioxide may be used in amounts up to about 2% by weight.
  • Glycerin may be incorporated to impart emollient characteristics to the finished bars or cakes and to enhance their gloss. Olive oil may also be used for this purpose and if desired, germicidal substances which are compatible and stable may be added.
  • Other texture modifying ingredients such as lanolin or aromatic additives such as perfume may also be utilized.
  • the process of this invention includes the step of admixing a higher molecular weight alcohol of the type described hereinabove with a butenedioic acid or anhydride. This step involves the addition of the alcohol and anhydride or acid to a vat or kettle and the application of sufficient heat to melt the alcohol component and initiate the reaction which, being exothermic, continues of its own accord. During this reaction the temperature preferably is maintained below about 100C. to minimize possible side reactions such as, e.g. diesterification, Diels- Alder type reactions, and the like.
  • the components of the reaction mixture will normally be used in quantities approximating their stoichiometric amounts.
  • the butenedioic anhydride or acid is normally added to the vat after the alcohol component has been melted and the rate of addition thereof can be varied to maintain the reaction mixture at a predetermined temperature preferably between about 55 and C.
  • the temperature is easily controlled in this manner since the latent heat of fusion of the anhydride roughly balances the heat of reaction of the aleohol with the anhydride.
  • the mass is slowly heated to a temperature between about and C. and the mass is maintained at this temperature for be tween 20 and 90 minutes to ensure completeness of the reaction.
  • the plasticizer will advantageously be added with agitation until a clear liquid is formed.
  • the temperature at this point should be approximately 45 to 55C.
  • the mass should be held just above its solidification tcmperature.
  • a predetermined amount of water at least that quantity necessary to get the sulphite to uid to a jelly-like paste andfinallyto-a stiffsoaplike paste.
  • After a temperature of between-95 and 100C. is maintained for'about-20 to-30 minutes, it may be desirable to add about one percent'of hydrogenfperox ide/130 vols. solution to oxidize .any sulphur dioxide that may be present.
  • EXAMPLE 1 Into a stainless steel reaction vessel fitted with a steam jacket, a gate type stirrer, and simple fume exhaust, there is charged 268 parts by weight of commercial lauryl alcohol and this is heated to between 50C. and 60C. at which temperature it is a free flowing oil. While stirring there is then added 134 parts of maleic anhydride granular solids at such a rate that the temperature remains between 50C. and 60C. The temperature is easily controlled by the rate of addition of the maleic anhydride, the latent heat of fusing of the solid roughly balancing the heat of reaction of the alcohol and the anhydride.
  • ('ommcrcial lauryl alcohol is the alcohol obtained by the catalytic hydrogenation of coconut oil or a fraction thereof from .-which the higher and lower homologues havebeen removed. Such a fraction may consist of 75% C,. CH, and 57: ofa mixture of predominantly C and C or it may be the corresponding similar product obtained by the Ziegler condensation ofethylene. or a very suitable product is a CPI-C", fraction formed as a petroleum hy-product.
  • the mass is slowly heated, with stirring, until at 85C. it clears to a uniform, pale straw-colored liquid. It is then heated to 95C. which temperature is maintained for 30 minutes, and then 380 parts of neutral, commercial, glyceryl monostearate is added and the whole mass stirred to a clear liquid having a temperature between 60C. and 70C.
  • commercial glyceryl monostearate is meant a glyceryl monostearate formed from commercial stearic acid.
  • the mixture is passed through a roll mill and crimped.
  • the crimped chips are fed to a conventional single barrel plodder having a worm diameter of 10.2 centimeters.
  • the barrel of the plodder is cooled slightly, and its nozzle is slightly heated.
  • the product is cut and pressed in the normal manner on conventional soap processing machinery.
  • the composition processes in a manner similar to soap and does not adhere to the die or other equip ment during the processing. All of the bars formed are of high quality.
  • the pH of the bars is 6.2 in the case of Examples 111, IV and V, and 6.1 for the bars of Example VI. All of the bars are characterized by exceptional resistance to slough and erosion, give satisfactory lather, and form no adherent scum or curd when used in a bath.
  • EXAMPLE Vll Into a reaction vessel equipped with steam jacket and stirrer, 260 parts of cocomonoethanolamide is charged. The temperature is raised to about 55C. and 100 parts of maleic anhydride is added. A temperature of between 50 and 60C. is maintained until the reaction is completed. The end of the reaction is checked by adding a few drops of the reaction product to a dilute solution of Na SO is a test tube, heating the test tube, and shaking. When the half ester reaction between the maleic anhydride and the cocomonoethanolamide is sufficiently complete, it disperses in the solution to give a characteristic, viscous streaming effect and subsequently a clear foaming solution. The half ester of maleic acid is a viscous syrup at room temperature.
  • the final product set to a firm soap-like mass, with good foaming and emollient characteristics which was formed into a cake by a conventional casting operation.
  • a cleansing bar comprising from about 40 to 95% by weight of substantially neutral water soluble alkali metal, alkaline earth metal or ammonium di-salts of sulfosuccinate mono esters and from about 5 to 60% by weight of a normally solid non-volatile organic plasticizer, said plasticizer having a melting point such that it is molten at about 95C and is chosen from the group consisting of fatty acid esters of polyhydric alcohols,
  • esters being the reaction product of a reactant having therein (1) a reactive hydroxyl group and, (2) an acyclic chain having from 12 to 18 carbon atoms wherein between 20 and 100% of said chains are alkyl chains having a chain length of 12 carbon atoms, with an alkali metal, alkaline earth metal or ammonium sulfite, said reaction product being produced in a reaction medium including said plasticizer.
  • the cleansing bar of claim 1 wherein said salt is selected from the group consisting of alkali metal and ammonium salts of a monoalkylsulfosuccinate.
  • a process for the production of cleansing cakes comprising; reacting an alcohol having an acyclic chain of from 12 to 18 carbon atoms wherein between 20 and 100% of said chains are alkyl chains having a chain length of 12 carbon atoms with a reactant chosen from the group consisting of maleic acid, butenedioic acid and fumaric acid to form a monoalkyl ester, reacting said monoalkyl ester with an alkali metal, alkaline earth metal or ammonium sulphite in the presence of about 5 to 10 percent water and a molten plasticizer chosen from the group consisting of fatty acid esters of polyhydric alcohols to form a water soluble di-salt of monoalkylsulfosuccinate; cooling the resulting prodnet, and forming the cooled product into cakes containing between about 40 and by weight of said monoalkylsulfosuccinate and from about 5 to 60% by weight of said plasticizer which plasticizes said monoalkylsulfosuccinate salt.
  • said monoalkyl ester is formed by reacting a compound selected from the group consisting of maleic anhydride, fumaric anhydride, maleic acid and fumaric acid with a reactant having therein a reactive hydroxyl group and an acyclic chain having from 12 to 18 carbon atoms wherein at least 20% of said chains are alkyl chains having a chain length of 12 carbon atoms.
  • plasticizer is glyceryl monostearate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US296414A 1965-08-24 1972-10-10 Detergent cake containing monoalkylsulfosuccinate and preparation Expired - Lifetime US3901832A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
CA798803A CA798803A (en) 1965-08-24 Detergents
DE19661617052 DE1617052A1 (de) 1965-08-24 1966-08-10 Stueckfoermige Reinigungsmittel
SE11102/66A SE343595B (en:Method) 1965-08-24 1966-08-16
AT07759/66A AT279009B (de) 1965-08-24 1966-08-16 Stueckfoermiges reinigungsmittel und verfahren zu dessen herstellung
CH1180166A CH488802A (de) 1965-08-24 1966-08-16 Stückförmiges Reinigungsmittel
FR73238A FR1489582A (fr) 1965-08-24 1966-08-17 Produit détergent contenant notamment un sulfosuccinate et son procédé de préparation
GB37066/66A GB1153303A (en) 1965-08-24 1966-08-18 Improvements in or relating to detergents.
BE685663D BE685663A (en:Method) 1965-08-24 1966-08-18
NL6611798A NL6611798A (en:Method) 1965-08-24 1966-08-22
DK433766A DK133054C (da) 1965-08-24 1966-08-24 Sebefrit rensemiddelstykke og fremgangsmade til dets fremstilling
US296414A US3901832A (en) 1965-08-24 1972-10-10 Detergent cake containing monoalkylsulfosuccinate and preparation

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
ZA654601 1965-08-24
US1476570A 1970-02-26 1970-02-26
US296414A US3901832A (en) 1965-08-24 1972-10-10 Detergent cake containing monoalkylsulfosuccinate and preparation

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Publication Number Publication Date
US3901832A true US3901832A (en) 1975-08-26

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US296414A Expired - Lifetime US3901832A (en) 1965-08-24 1972-10-10 Detergent cake containing monoalkylsulfosuccinate and preparation

Country Status (11)

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US (1) US3901832A (en:Method)
AT (1) AT279009B (en:Method)
BE (1) BE685663A (en:Method)
CA (1) CA798803A (en:Method)
CH (1) CH488802A (en:Method)
DE (1) DE1617052A1 (en:Method)
DK (1) DK133054C (en:Method)
FR (1) FR1489582A (en:Method)
GB (1) GB1153303A (en:Method)
NL (1) NL6611798A (en:Method)
SE (1) SE343595B (en:Method)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4234464A (en) * 1979-04-09 1980-11-18 Gaf Corporation Detergent bar composition and binder therefor
US4335025A (en) * 1980-02-19 1982-06-15 Witco Chemical Corporation Process for the preparation of synthetic detergent bars, and products produced thereby
US4647394A (en) * 1981-04-07 1987-03-03 Mitsubishi Chemical Industries Limited Soap composition
US4722801A (en) * 1986-06-20 1988-02-02 Kiwi Brands, Inc. Toilet bowl cleaner in cake form containing a polyethyleneglycol distearate
US4780236A (en) * 1986-06-20 1988-10-25 Kiwi Brands, Inc. Lavoratory cleansing block containing polyethylene gycol disteatrate, guar gum and sodium chloride
US5015414A (en) * 1988-09-08 1991-05-14 Kao Corporation Low-irritant detergent composition containing alkyl saccharide and sulfosuccinate surfactants
US5372751A (en) * 1990-02-09 1994-12-13 Lever Brothers Company, Division Of Conopco, Inc. Acyl isethionate skin cleaning compositions containing betaines, amido sulfosuccinates or combinations of the two
US5424010A (en) * 1993-01-06 1995-06-13 Duliba; Edward P. Light duty liquid detergent composition containing 3-methyl-3-methoxy-butanol
US5543072A (en) * 1992-10-05 1996-08-06 Mona Industries, Inc. Synthetic detergent bars and method of making the same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3989647A (en) 1973-04-26 1976-11-02 Lever Brothers Company Quick lathering toilet bars and method of making same
US4039562A (en) 1975-02-21 1977-08-02 Rewo Chemische Werke G.M.B.H. Process for preparing sulfosuccinates

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2316234A (en) * 1940-11-30 1943-04-13 Allied Chem & Dye Corp Ester of sulphosuccinic acid
US2373863A (en) * 1943-04-15 1945-04-17 American Cyanamid Co Nonalkaline detergent composition
US2567159A (en) * 1949-11-04 1951-09-04 American Cyanamid Co Wetting and detergent composition
US2678921A (en) * 1948-08-04 1954-05-18 Colgate Palmolive Co Process of producing a milled nonsoap detergent in bar form
US2972583A (en) * 1956-05-17 1961-02-21 Colgate Palmolive Co Detergent cake and method of making same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2316234A (en) * 1940-11-30 1943-04-13 Allied Chem & Dye Corp Ester of sulphosuccinic acid
US2373863A (en) * 1943-04-15 1945-04-17 American Cyanamid Co Nonalkaline detergent composition
US2678921A (en) * 1948-08-04 1954-05-18 Colgate Palmolive Co Process of producing a milled nonsoap detergent in bar form
US2567159A (en) * 1949-11-04 1951-09-04 American Cyanamid Co Wetting and detergent composition
US2972583A (en) * 1956-05-17 1961-02-21 Colgate Palmolive Co Detergent cake and method of making same

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4234464A (en) * 1979-04-09 1980-11-18 Gaf Corporation Detergent bar composition and binder therefor
US4335025A (en) * 1980-02-19 1982-06-15 Witco Chemical Corporation Process for the preparation of synthetic detergent bars, and products produced thereby
US4647394A (en) * 1981-04-07 1987-03-03 Mitsubishi Chemical Industries Limited Soap composition
US4722801A (en) * 1986-06-20 1988-02-02 Kiwi Brands, Inc. Toilet bowl cleaner in cake form containing a polyethyleneglycol distearate
US4780236A (en) * 1986-06-20 1988-10-25 Kiwi Brands, Inc. Lavoratory cleansing block containing polyethylene gycol disteatrate, guar gum and sodium chloride
US5015414A (en) * 1988-09-08 1991-05-14 Kao Corporation Low-irritant detergent composition containing alkyl saccharide and sulfosuccinate surfactants
US5372751A (en) * 1990-02-09 1994-12-13 Lever Brothers Company, Division Of Conopco, Inc. Acyl isethionate skin cleaning compositions containing betaines, amido sulfosuccinates or combinations of the two
US5543072A (en) * 1992-10-05 1996-08-06 Mona Industries, Inc. Synthetic detergent bars and method of making the same
US5424010A (en) * 1993-01-06 1995-06-13 Duliba; Edward P. Light duty liquid detergent composition containing 3-methyl-3-methoxy-butanol

Also Published As

Publication number Publication date
GB1153303A (en) 1969-05-29
DK133054B (da) 1976-03-15
CH488802A (de) 1970-04-15
SE343595B (en:Method) 1972-03-13
CA798803A (en) 1968-11-12
FR1489582A (fr) 1967-07-21
BE685663A (en:Method) 1967-02-20
NL6611798A (en:Method) 1967-02-27
DE1617052A1 (de) 1971-03-18
DK133054C (da) 1976-08-30
AT279009B (de) 1970-02-25

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