CA2114952A1 - Free-flowing water-containing alkyl sulfate pastes - Google Patents
Free-flowing water-containing alkyl sulfate pastesInfo
- Publication number
- CA2114952A1 CA2114952A1 CA002114952A CA2114952A CA2114952A1 CA 2114952 A1 CA2114952 A1 CA 2114952A1 CA 002114952 A CA002114952 A CA 002114952A CA 2114952 A CA2114952 A CA 2114952A CA 2114952 A1 CA2114952 A1 CA 2114952A1
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- Canada
- Prior art keywords
- weight
- alkyl
- sulfate
- formula
- alkenyl
- 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.)
- Abandoned
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/14—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and unsaturated
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of 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
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Materials Engineering (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Abstract
The aim of the invention is to the improve the flow behaviour and pumpability of highly concentrated aqueous alkyl sulphate slurries, in particular at low temperatures and low shear gradients.
This is achieved essentially by mixing the aqueous slurry from 50 to 80 % by wt. of an alkyl sulphate of the formula R1-O-SO3M1, in which R1 is a straight-chain or branched-chain alkyl group with 12 to 22 C-atoms and M1 is an alkali-metal, ammonium, alkylammonium or hydroxyalkylammonium ion, and an alkenyl sulphate of the formula R2-O-SO3M2, in which R2 is an alkenyl group with 16 to 22 C-atoms and 1, 2 or 3 double bonds and M2 is an alkali-metal, ammonium, alkylammonium or hydroxyalkylammonium ion, in the proportions of alkyl sulphate to alkenyl sulphate of 10:1 to 1:3.
This is achieved essentially by mixing the aqueous slurry from 50 to 80 % by wt. of an alkyl sulphate of the formula R1-O-SO3M1, in which R1 is a straight-chain or branched-chain alkyl group with 12 to 22 C-atoms and M1 is an alkali-metal, ammonium, alkylammonium or hydroxyalkylammonium ion, and an alkenyl sulphate of the formula R2-O-SO3M2, in which R2 is an alkenyl group with 16 to 22 C-atoms and 1, 2 or 3 double bonds and M2 is an alkali-metal, ammonium, alkylammonium or hydroxyalkylammonium ion, in the proportions of alkyl sulphate to alkenyl sulphate of 10:1 to 1:3.
Description
3 j ,i Free- ~lowing water-con~aining ~lkyl ~ul f ate pa~te~
This invention relates to free-flowing, pumpable water-containing alkyl sulfate pastes, to a process for the production of alkyl sulfate pastes having improved flow properties by addition of alkenyl sulfates and to the use of such pastes for the production o~ detergents and cleaning preparations.
Anionic surfactants of the alkyl sul~ate type, more especially those containing C~61~ alkyl radicals, show excellent detergent properties and ar~ used both in li-0 quid and in powder-form detergents and cleaning prepar~
ations.
The detergents in question are c~enerally produced from water-containing alkyl sulfate pastes. To avoid unnecessary mass transport, it is an advan~age if water-containing surfactant pastes have a high solids content.However, alkyl sulfate pastes can only be concentrated to a certain solids content. In addition, pastes such as these show non-newtonian flow behavior. Above a limit o~
around 55~ by weigh~ solids, the viscosity generally reaches such high values that the pumpability of the surfactant solutions is no longer guaranteed, even at elevated temperatures. Thus, water-containing fatty alcohol sulfate pastes with solids contents of 30 to 70%
by weight have such high viscosities and yield points, even at ambient temperature, that they often cannot be transferred from one vessel to another or pump-circu-lated.
According to EP 024 711, polyalkyl ether glycol sulfates are added to high~viscosity surfactant concen-trates to reduce their viscosity Whereas compounds suchas these are eminently suitable for reducing the vis-cosity of alkyl ether sulfate, alkylaryl ether sulfate, , ,i, .1. ~1 ~ c) ,,i '' Wo 93/03128 2 PCT/EP92/0170~
alkyl benzenesulPonate and alkylaryl ~ulfosuccinate solutions, their performance in the presence vf alkyl sulfates, particularly linear primary alkyl sulfates, is often unsatisfactory.
DE-OS 34 47 ~59 describes the use of alkanesul-fonates as viscosi~y regulators for high-viscosity anionic surfactant concentra~es, more especially salts of ~-sulfofatty acid esters~
DE-O~ 37 18 8g6 describes the use of alkoxylated alcohols as viscosity regulators for high-viscosity alkyl benzenesulfonate concentrates.
It has now surprising1y been found that water-containing mixtures of unsaturated and saturated alkyl sulfates have a low viscosity and a low yield point so that the unfavorable flow behavior typical of alkyl sulfates based solely on saturated alcohols is o~ercome.
It is thus possible to produce high-solids alkyl sulfate pastes which are flowable and pumpable, even at low temperatures ~nd low shear rates.
Accordingly, the present invention relates to a water-containing, free-flowing and pum~able alkyl sulfate paste having a viscosity, as measured at a shear rate of 10 s~1, of 5 Pa.s to 100 Pa.s and preferably 5 Pa.s to S0 Pa.s at temperatures of~50 to 90C which contain from 15%
by weight to 65~ by weight and more particularly from 25%
by weight to 50~ by wei~ht of an alkyl sulfate corre-sponding to formula I:~
.
~ Rl-O-SO3M~
..
in which Rl is a linear or branched Cl222 alkyl radical and Ml is an alkali~ metal,~ ammonium, alkyl ammonium or hydroxyalkyl ammonium ion,~ ~
f~om 5% by weight to 65% by wei~ht and more particularly from 15%~by weight to 65% by weight of an alkenyl sulfate :~:
5~
Wo 93/03128 3 PCT/EP92/0170 corresponding to formula II:
R2-0-S03M2 (II) in which ~2 is an alkenyl rad.ical containing 16 to 22 carbon atoms and 1, 2 or 3 double bonds and M2 is an alkali metal, ammonium, alkyl ammoni.um or hydroxyalkyl ammonium ion, ~`
and from 20% by weight to S0% by weight o~ water.
The present invention also relates to a process ~or the production o~ a free-flowing, pumpable water-contain-ing alkyl ~ulfate paste having a solidis content of 50~ by weight to 80% by weight and, m~re particularly, 60% by weight to 75~ by weight, characterized in that an aqueous paste containing 50% ~y weight to 80~ by weight of an alkyl sulfate corresponding to fo~mula I:
R1-0-SO3~1 (I) , ., in which Rl is a linear or branched C1~22 alkyl radical and M1 is an alkali metal, ammonium, alkyl ammonium or hydroxyalkyl ammonium ion, is mixed with an alkenyl sulfate corresponding to formula II:
R2-0-SO3M~ (II) :, in which R2 is an alkenyl radical containing 16 to 22 carbon atoms and 1, 2 or 3 double bonds and M2 is an alkali metaI, ammonium, alkyl ammonium or hydroxyalkyl . , I j , , ammonium lon, in a ratio by weight of alkyl sulfate (I) to alkenyl sulfate (II) Oc lO:1 to 1:3.
The alkyl sulfate corresponding to formula I and the alkenyl sulfate oorresponding to formula II are prefer-J 'J
ably mixed with one another in a ratio by weight of alkyl sulfate to alkenyl sulfate of 7:1 to 1:2.
In one preferred embodiment of the process according to the invention, a water-containing paste containing an alkenyl sulfate corresponding to formula II is mixed with such a quantity of a water-containing paste containing an alkyl sulPate corresponding to ~ormula I that the sum total of alkyl sulfate and alkenyl sulfakQ in the result-ing water-containiny paste is 45% by weight to 80~ by weight and more particularly 50% by weight to 75% by weight and the resulting paste contains 20% by weight to 55% by weight and more particularly 25% by weight to 50 by weight of water.
The alkyl sul,fates corresponding to formula I are known anîonic surfactants which are generally obtained by reaction of aliphatic primary alcohols with a sulfating agent, for example sulfur trioxide or chlorosulfonic acid. Alkyl sulfates to which the process according to the invention extends are preferably derived from C1222 fatty alcohols. Typical examples of such alcohols are lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol or behenyl alcohol. A particularly drastic reduction in the viscosity o~ the paste is obser~ed in the case of alkyl sulfates derived from alcohols contain-ing 12 to 18 carbon atoms and more particularly 16 to 18 carbon atoms.
The alkyl sulfates may also be derived from techni-cal alcohol mixtures such as~are ~ormed, for example, in the hydrogenation of technical fatty acid ester mixtures 30, of natural origin or in the h~drogenation of aldehydes from Roelen's oxo synthesis. Alkyl sulfates based on - technical coconut oil or hydrogenated palm oil alcohol ; ; cuts are pre~erred. Alcohols~such as these are under-stood to be primary fatty alcohoIs which have on average the following C chain distribution:
, ,., l 1 ~1 .~ i '~
Wo 93/03128 5 PCT/EP92/01704 Coconut oil alcohol Hydrogenated palm oil alcohol __ _ C10:0 - 3% by weight C1248 - 58% by weight C1419 - 24% by weight 0 - 3~ by weight C16:9 ~ 12% by weight45 ~ 55% by weight C18:11 ~ 14~ by weight45 ~ 55% by weight C2~ 0 - 3% by weight The sulfation products of unsaturated alcohols to b~
added to the alkyl sulfate pastes in accordance with the invention are compounds which are obtained by reaction of mono-, di- or tri-unsaturated alcohols with sulfating agents, more particularly gaseous sulfur trioxide, and subsequent neutralization and hydrolysis of the reaction products formed. One process for the production of such compounds is described, for example, by M. Morak and R.
Audiova in Tenside Detergénts 15 ~1978), 299. ..
Since, where unsaturated alcohols are used, the sulfation reactior can also be accompanied by addition of the sulfur trioxide onto the double bond, the alkenyl sulfate paste may also contain substances which contain an internal sulfonate group or a sulfonate group and a :.
sulfate group. The percentage content of these internal sulfonation products is normally from 3 to 20% by weight, based on the quantity of alkenyl sulfate corresponding to formula II. If desired, this quantity may be reduced to zero by corresponding~purifying operations.
Typical examples of` unsaturated alcohols of which the sulfates corresponding to formula II may be used as the viscosity-reducing component according to the inven-tion are, in particular, p~lmitoleyl alcohol, oleyl alcohol, elaidyl alcohol,;petroselinyl alcohol, linoleyl alcohol, linolenyl alcohol, gadoleyl alcohol or erucyl alcohol. Oleyl alcohol is preferably used. Sulfation ~ ' , ' ,~ ) 5 ';', Wo 93/03128 6 PcT/EPs~/01704 products of technical mixtures of the unsaturated alco hols mentioned with one another or with certain quanti-ties of saturated alcohols of corresponding chain length may also be used in the process according to khe inven-tion. Pastes such as these preferably contain no morethan 70% by weight and, more preferably, from 2~ by weight to 60~ by weight of saturated alkyl sulfate~
The two starting pastes and also the alkyl sulfate paste according to the invention may contain as ~urther constituents small quantities o~ generally not more than 10% by weight and more particularly from ~ to 5% by weight, based on the particular paste, of inorganic salts, particularly sulfates, resulting from the reaction ,. ~
of any excess sulfating agent with the neutralization base in the production process.
The highly concentrated alkyl sulfate pastes accord-ing to the invention have excellent detergent properties and high solubility in cold water. Accordingly, they are preferably used for the production of powder-f~rm or liquid laundry detergents, dishwashing detergents and cleaning products and also cosmetic products, more particularly hair-care and body-care products.
The products in question may readily be prepared by diluting the pastès produced by the process according to the invention with water to the desired active substance concentration~ Other constituents typical of such products may also be added, including in particular builders, such as zeolites and layer silicates, corrosion inhibitors, bleaching agents, bleach activators, optical 30j brighteners, enzymes, redeposition inhibitors~ antlmicro bial agents, water-miscible solvents, abrasives, foam stabilizers, preservatives, pH regulators, dyes and frayrances and additional~surfactants.
,.J~ J.j,~ :
wo 93/03128 - 7 pcT/Eps2~ol7o4 Examples Example 1 2~0 g (1 molP) of a technical oleyl/cetyl alcohol (HD-Ocenol~ 50-55, a product of Henkel KGaA) with the followiny composition: .:
Myristyl alcohol : 5% by weighk Cetyl alcohol : 30% by weight 10 Oleyl alcohol : 65% by weighk Io~ine value : 53 Hydroxyl value : 215 were introduced into a 1 liter sulfonation reactor equipped with a jacket cooling system and gas inlet pipe and reacted at 45C with 84 g (1.05 mole~ of sulfur trioxide. The sulfur trio~ide was driven out by heating from a corresponding quantity of 65~ by weight oleum, diluted with nitrogen to a concentration of 5~ by volume and introduced into the starting product over a period of 30 minutes. The crude sul~onation product was neutral- :
ized and, at the same time, hydrolyzed at 80C with 2~4 -;
g of a 20% by weight a~ueous sodium hydroxide solution.
The reaction product was then adjusted with sodium hydroxide to a pH value of 10. A paste-form product having the following characteristic data was obtained:
Anionic surfactant content : 59.7% by weight 30, - Alkenyl sulfate component : 27.5% by weight - Alkyl sulfate component : 20.7% by weight - Sulfonate component : 11.5% by weight Unsulfonated components : 2.0% by weight 50dium sulfate ~ : 2.8% by weight 35 Water : : 35.5% by weight :
v 1 . `.1 c) ,~
WO 93/03128 8 PCT/EP92~~01704 The an.ionic surfactant content and the unsulfonated components were determined in accordance with D~F-E~n-heitsmetho~en, Btuttgaxt~ 1950-19~4t ~-III-10 and G~
6b. The sulfate conten~ was calculated as sodium sul-fate, khe water content being determined by the Fischer method.
Example 2 Pastes P1 to P3 according to the invention charac-terized in the followiny Table were prepared ~y addingthe product according to Example 1 to a 55~ by weight water-containing paste of a saturated C16/18 alkyl sulfate (Sulfopon~ T 55, a product of Henkel KGaA) in the quanti-ties shown in the following Table and mixing. The yield points and viscosities (at a shear rate D of 10 ,5-1~ of the pastes thus prepared were measured at 60C using a shear-stress-controlled rotational rheometer (Carri-Med~ .
CS 100) with a plate/plate measuring system. The simil-arly determined values of a solution (C1) free from alkenyl sulfate are shown ~or comparison.
Table : Alkenyl and alkyl sul~ate conten~s I % by wei~ht active substance~ and flow data of the pastes __ _ P1 P2 P3 ~1 _ _ _ _ Alkenyl sulfatea) 6.88 13.75 20.62 _ _ Alkyl sulfateb) ~ 46.43 37.85 29.28 55 .~ I Yield point CPa~ 105 60 25 138 Viscosity CPa.s] 19 12 7.5 32 a) From corresponding quantities of th~ product of Example 1 b) Sum of Na C16/18 alkyl :sulfate (Sulfopon~ T 55, a product of Henkel KGa~) and alkyl sulfate from the : product of~Example l ,:
This invention relates to free-flowing, pumpable water-containing alkyl sulfate pastes, to a process for the production of alkyl sulfate pastes having improved flow properties by addition of alkenyl sulfates and to the use of such pastes for the production o~ detergents and cleaning preparations.
Anionic surfactants of the alkyl sul~ate type, more especially those containing C~61~ alkyl radicals, show excellent detergent properties and ar~ used both in li-0 quid and in powder-form detergents and cleaning prepar~
ations.
The detergents in question are c~enerally produced from water-containing alkyl sulfate pastes. To avoid unnecessary mass transport, it is an advan~age if water-containing surfactant pastes have a high solids content.However, alkyl sulfate pastes can only be concentrated to a certain solids content. In addition, pastes such as these show non-newtonian flow behavior. Above a limit o~
around 55~ by weigh~ solids, the viscosity generally reaches such high values that the pumpability of the surfactant solutions is no longer guaranteed, even at elevated temperatures. Thus, water-containing fatty alcohol sulfate pastes with solids contents of 30 to 70%
by weight have such high viscosities and yield points, even at ambient temperature, that they often cannot be transferred from one vessel to another or pump-circu-lated.
According to EP 024 711, polyalkyl ether glycol sulfates are added to high~viscosity surfactant concen-trates to reduce their viscosity Whereas compounds suchas these are eminently suitable for reducing the vis-cosity of alkyl ether sulfate, alkylaryl ether sulfate, , ,i, .1. ~1 ~ c) ,,i '' Wo 93/03128 2 PCT/EP92/0170~
alkyl benzenesulPonate and alkylaryl ~ulfosuccinate solutions, their performance in the presence vf alkyl sulfates, particularly linear primary alkyl sulfates, is often unsatisfactory.
DE-OS 34 47 ~59 describes the use of alkanesul-fonates as viscosi~y regulators for high-viscosity anionic surfactant concentra~es, more especially salts of ~-sulfofatty acid esters~
DE-O~ 37 18 8g6 describes the use of alkoxylated alcohols as viscosity regulators for high-viscosity alkyl benzenesulfonate concentrates.
It has now surprising1y been found that water-containing mixtures of unsaturated and saturated alkyl sulfates have a low viscosity and a low yield point so that the unfavorable flow behavior typical of alkyl sulfates based solely on saturated alcohols is o~ercome.
It is thus possible to produce high-solids alkyl sulfate pastes which are flowable and pumpable, even at low temperatures ~nd low shear rates.
Accordingly, the present invention relates to a water-containing, free-flowing and pum~able alkyl sulfate paste having a viscosity, as measured at a shear rate of 10 s~1, of 5 Pa.s to 100 Pa.s and preferably 5 Pa.s to S0 Pa.s at temperatures of~50 to 90C which contain from 15%
by weight to 65~ by weight and more particularly from 25%
by weight to 50~ by wei~ht of an alkyl sulfate corre-sponding to formula I:~
.
~ Rl-O-SO3M~
..
in which Rl is a linear or branched Cl222 alkyl radical and Ml is an alkali~ metal,~ ammonium, alkyl ammonium or hydroxyalkyl ammonium ion,~ ~
f~om 5% by weight to 65% by wei~ht and more particularly from 15%~by weight to 65% by weight of an alkenyl sulfate :~:
5~
Wo 93/03128 3 PCT/EP92/0170 corresponding to formula II:
R2-0-S03M2 (II) in which ~2 is an alkenyl rad.ical containing 16 to 22 carbon atoms and 1, 2 or 3 double bonds and M2 is an alkali metal, ammonium, alkyl ammoni.um or hydroxyalkyl ammonium ion, ~`
and from 20% by weight to S0% by weight o~ water.
The present invention also relates to a process ~or the production o~ a free-flowing, pumpable water-contain-ing alkyl ~ulfate paste having a solidis content of 50~ by weight to 80% by weight and, m~re particularly, 60% by weight to 75~ by weight, characterized in that an aqueous paste containing 50% ~y weight to 80~ by weight of an alkyl sulfate corresponding to fo~mula I:
R1-0-SO3~1 (I) , ., in which Rl is a linear or branched C1~22 alkyl radical and M1 is an alkali metal, ammonium, alkyl ammonium or hydroxyalkyl ammonium ion, is mixed with an alkenyl sulfate corresponding to formula II:
R2-0-SO3M~ (II) :, in which R2 is an alkenyl radical containing 16 to 22 carbon atoms and 1, 2 or 3 double bonds and M2 is an alkali metaI, ammonium, alkyl ammonium or hydroxyalkyl . , I j , , ammonium lon, in a ratio by weight of alkyl sulfate (I) to alkenyl sulfate (II) Oc lO:1 to 1:3.
The alkyl sulfate corresponding to formula I and the alkenyl sulfate oorresponding to formula II are prefer-J 'J
ably mixed with one another in a ratio by weight of alkyl sulfate to alkenyl sulfate of 7:1 to 1:2.
In one preferred embodiment of the process according to the invention, a water-containing paste containing an alkenyl sulfate corresponding to formula II is mixed with such a quantity of a water-containing paste containing an alkyl sulPate corresponding to ~ormula I that the sum total of alkyl sulfate and alkenyl sulfakQ in the result-ing water-containiny paste is 45% by weight to 80~ by weight and more particularly 50% by weight to 75% by weight and the resulting paste contains 20% by weight to 55% by weight and more particularly 25% by weight to 50 by weight of water.
The alkyl sul,fates corresponding to formula I are known anîonic surfactants which are generally obtained by reaction of aliphatic primary alcohols with a sulfating agent, for example sulfur trioxide or chlorosulfonic acid. Alkyl sulfates to which the process according to the invention extends are preferably derived from C1222 fatty alcohols. Typical examples of such alcohols are lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol or behenyl alcohol. A particularly drastic reduction in the viscosity o~ the paste is obser~ed in the case of alkyl sulfates derived from alcohols contain-ing 12 to 18 carbon atoms and more particularly 16 to 18 carbon atoms.
The alkyl sulfates may also be derived from techni-cal alcohol mixtures such as~are ~ormed, for example, in the hydrogenation of technical fatty acid ester mixtures 30, of natural origin or in the h~drogenation of aldehydes from Roelen's oxo synthesis. Alkyl sulfates based on - technical coconut oil or hydrogenated palm oil alcohol ; ; cuts are pre~erred. Alcohols~such as these are under-stood to be primary fatty alcohoIs which have on average the following C chain distribution:
, ,., l 1 ~1 .~ i '~
Wo 93/03128 5 PCT/EP92/01704 Coconut oil alcohol Hydrogenated palm oil alcohol __ _ C10:0 - 3% by weight C1248 - 58% by weight C1419 - 24% by weight 0 - 3~ by weight C16:9 ~ 12% by weight45 ~ 55% by weight C18:11 ~ 14~ by weight45 ~ 55% by weight C2~ 0 - 3% by weight The sulfation products of unsaturated alcohols to b~
added to the alkyl sulfate pastes in accordance with the invention are compounds which are obtained by reaction of mono-, di- or tri-unsaturated alcohols with sulfating agents, more particularly gaseous sulfur trioxide, and subsequent neutralization and hydrolysis of the reaction products formed. One process for the production of such compounds is described, for example, by M. Morak and R.
Audiova in Tenside Detergénts 15 ~1978), 299. ..
Since, where unsaturated alcohols are used, the sulfation reactior can also be accompanied by addition of the sulfur trioxide onto the double bond, the alkenyl sulfate paste may also contain substances which contain an internal sulfonate group or a sulfonate group and a :.
sulfate group. The percentage content of these internal sulfonation products is normally from 3 to 20% by weight, based on the quantity of alkenyl sulfate corresponding to formula II. If desired, this quantity may be reduced to zero by corresponding~purifying operations.
Typical examples of` unsaturated alcohols of which the sulfates corresponding to formula II may be used as the viscosity-reducing component according to the inven-tion are, in particular, p~lmitoleyl alcohol, oleyl alcohol, elaidyl alcohol,;petroselinyl alcohol, linoleyl alcohol, linolenyl alcohol, gadoleyl alcohol or erucyl alcohol. Oleyl alcohol is preferably used. Sulfation ~ ' , ' ,~ ) 5 ';', Wo 93/03128 6 PcT/EPs~/01704 products of technical mixtures of the unsaturated alco hols mentioned with one another or with certain quanti-ties of saturated alcohols of corresponding chain length may also be used in the process according to khe inven-tion. Pastes such as these preferably contain no morethan 70% by weight and, more preferably, from 2~ by weight to 60~ by weight of saturated alkyl sulfate~
The two starting pastes and also the alkyl sulfate paste according to the invention may contain as ~urther constituents small quantities o~ generally not more than 10% by weight and more particularly from ~ to 5% by weight, based on the particular paste, of inorganic salts, particularly sulfates, resulting from the reaction ,. ~
of any excess sulfating agent with the neutralization base in the production process.
The highly concentrated alkyl sulfate pastes accord-ing to the invention have excellent detergent properties and high solubility in cold water. Accordingly, they are preferably used for the production of powder-f~rm or liquid laundry detergents, dishwashing detergents and cleaning products and also cosmetic products, more particularly hair-care and body-care products.
The products in question may readily be prepared by diluting the pastès produced by the process according to the invention with water to the desired active substance concentration~ Other constituents typical of such products may also be added, including in particular builders, such as zeolites and layer silicates, corrosion inhibitors, bleaching agents, bleach activators, optical 30j brighteners, enzymes, redeposition inhibitors~ antlmicro bial agents, water-miscible solvents, abrasives, foam stabilizers, preservatives, pH regulators, dyes and frayrances and additional~surfactants.
,.J~ J.j,~ :
wo 93/03128 - 7 pcT/Eps2~ol7o4 Examples Example 1 2~0 g (1 molP) of a technical oleyl/cetyl alcohol (HD-Ocenol~ 50-55, a product of Henkel KGaA) with the followiny composition: .:
Myristyl alcohol : 5% by weighk Cetyl alcohol : 30% by weight 10 Oleyl alcohol : 65% by weighk Io~ine value : 53 Hydroxyl value : 215 were introduced into a 1 liter sulfonation reactor equipped with a jacket cooling system and gas inlet pipe and reacted at 45C with 84 g (1.05 mole~ of sulfur trioxide. The sulfur trio~ide was driven out by heating from a corresponding quantity of 65~ by weight oleum, diluted with nitrogen to a concentration of 5~ by volume and introduced into the starting product over a period of 30 minutes. The crude sul~onation product was neutral- :
ized and, at the same time, hydrolyzed at 80C with 2~4 -;
g of a 20% by weight a~ueous sodium hydroxide solution.
The reaction product was then adjusted with sodium hydroxide to a pH value of 10. A paste-form product having the following characteristic data was obtained:
Anionic surfactant content : 59.7% by weight 30, - Alkenyl sulfate component : 27.5% by weight - Alkyl sulfate component : 20.7% by weight - Sulfonate component : 11.5% by weight Unsulfonated components : 2.0% by weight 50dium sulfate ~ : 2.8% by weight 35 Water : : 35.5% by weight :
v 1 . `.1 c) ,~
WO 93/03128 8 PCT/EP92~~01704 The an.ionic surfactant content and the unsulfonated components were determined in accordance with D~F-E~n-heitsmetho~en, Btuttgaxt~ 1950-19~4t ~-III-10 and G~
6b. The sulfate conten~ was calculated as sodium sul-fate, khe water content being determined by the Fischer method.
Example 2 Pastes P1 to P3 according to the invention charac-terized in the followiny Table were prepared ~y addingthe product according to Example 1 to a 55~ by weight water-containing paste of a saturated C16/18 alkyl sulfate (Sulfopon~ T 55, a product of Henkel KGaA) in the quanti-ties shown in the following Table and mixing. The yield points and viscosities (at a shear rate D of 10 ,5-1~ of the pastes thus prepared were measured at 60C using a shear-stress-controlled rotational rheometer (Carri-Med~ .
CS 100) with a plate/plate measuring system. The simil-arly determined values of a solution (C1) free from alkenyl sulfate are shown ~or comparison.
Table : Alkenyl and alkyl sul~ate conten~s I % by wei~ht active substance~ and flow data of the pastes __ _ P1 P2 P3 ~1 _ _ _ _ Alkenyl sulfatea) 6.88 13.75 20.62 _ _ Alkyl sulfateb) ~ 46.43 37.85 29.28 55 .~ I Yield point CPa~ 105 60 25 138 Viscosity CPa.s] 19 12 7.5 32 a) From corresponding quantities of th~ product of Example 1 b) Sum of Na C16/18 alkyl :sulfate (Sulfopon~ T 55, a product of Henkel KGa~) and alkyl sulfate from the : product of~Example l ,:
Claims (8)
1. A water-containing, free-flowing and pumpable alkyl sulfate paste with a viscosity of 5 Pa.s to 100 Pa.s at a shear rate of 10 s-1 and at a temperature of 50°C to 90°C, characterized in that it contains from 15% by weight to 65% by weight of an alkyl sulfate corresponding to formula I:
R1-O-SO3M1 (I) in which R1 is a linear or branched C12-22 alkyl radical and M1 is an alkali metal, ammonium, alkyl ammonium or hydroxyalkyl ammonium ion, from 5% by weight to 65% by weight of an alkenyl sulfate corresponding to formula II:
R2-O-SO3M2 (II) in which R2 is an alkenyl radical containing 16 to 22 carbon atoms and 1, 2 or 3 double bonds and M2 is an alkali metal, ammonium, alkyl ammonium or hydroxyalkyl ammonium ion, and from 20% by weight to 50% by weight of water.
R1-O-SO3M1 (I) in which R1 is a linear or branched C12-22 alkyl radical and M1 is an alkali metal, ammonium, alkyl ammonium or hydroxyalkyl ammonium ion, from 5% by weight to 65% by weight of an alkenyl sulfate corresponding to formula II:
R2-O-SO3M2 (II) in which R2 is an alkenyl radical containing 16 to 22 carbon atoms and 1, 2 or 3 double bonds and M2 is an alkali metal, ammonium, alkyl ammonium or hydroxyalkyl ammonium ion, and from 20% by weight to 50% by weight of water.
2. A water-containing alkyl sulfate paste as claimed in claim 1, characterized in that the alkyl sulfate corre-sponding to formula I has a linear alkyl radical R1 containing 12 to 18 carbon atoms and more particularly 16 to 18 carbon atoms.
3. A water-containing alkyl sulfate paste as claimed in claim 1 or 2, characterized in that the alkenyl sulfate corresponding to formula II has a linear alkyl radical R2 containing 16 to 18 carbon atoms.
4. A water-containing alkyl sulfate paste as claimed in any of claims 1 to 3, characterized in that it contains from 25% by weight to 50% by weight of an alkyl sulfate corresponding to formula I and from 15% by weight to 65%
by weight of an alkenyl sulfate corresponding to formula II.
by weight of an alkenyl sulfate corresponding to formula II.
5. A water-containing alkyl sulfate paste as claimed in any of claims 1 to 4, characterized in that it has a vis-cosity of 5 Pa.s to 50 Pa.s at a shear rate of 10 s-1 and at a temperature of 50°C to 90°C.
6. A process for the production of a free-flowing, pumpable water-containing alkyl sulfate paste with a solids content of 50 to 80% by weight, characterized in that an aqueous paste containing 50% by weight to 80% by weight of an alkyl sulfate corresponding to formula I:
R1-O-SO3M1 (I) in which R1 is a linear or branched C12-22 alkyl radical and M1 is an alkali metal, ammonium, alkyl ammonium or hydroxyalkyl ammonium ion, is mixed with an alkenyl sulfate corresponding to formula II:
R2-O-SO3M2 (II) in which R2 is an alkenyl radical containing 16 to 22 carbon atoms and 1, 2 or 3 double bonds and M2 is an alkali metal, ammonium, alkyl ammonium or hydroxyalkyl ammonium ion, in a ratio by weight of alkyl sulfate corresponding to formula I to alkenyl sulfate corresponding to formula II
of 10:1 to 1:3.
R1-O-SO3M1 (I) in which R1 is a linear or branched C12-22 alkyl radical and M1 is an alkali metal, ammonium, alkyl ammonium or hydroxyalkyl ammonium ion, is mixed with an alkenyl sulfate corresponding to formula II:
R2-O-SO3M2 (II) in which R2 is an alkenyl radical containing 16 to 22 carbon atoms and 1, 2 or 3 double bonds and M2 is an alkali metal, ammonium, alkyl ammonium or hydroxyalkyl ammonium ion, in a ratio by weight of alkyl sulfate corresponding to formula I to alkenyl sulfate corresponding to formula II
of 10:1 to 1:3.
7. A process as claimed in claim 6, characterized in that the alkenyl sulfate II and the alkyl sulfate I are mixed in a ratio by weight of alkyl sulfate to alkenyl sulfate of 7:1 to 1:2.
8. A process as claimed in claim 6 or 7, characterized in that a water-containing paste containing an alkenyl sulfate corresponding to formula II is mixed with a water-containing paste containing an alkyl sulfate corresponding to formula I in such a quantity that the sum total of alkyl sulfate and alkenyl sulfate in the resulting aqueous paste is 45% by weight to 80% by weight and more particularly 50% by weight to 75% by weight and the resulting paste contains 20% by weight to 55% by weight and more particularly 25% by weight to 50% by weight of water.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4125792.8 | 1991-08-03 | ||
| DE4125792A DE4125792A1 (en) | 1991-08-03 | 1991-08-03 | FLOWABLE WAESSED ALKYLSULFATE PASTE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2114952A1 true CA2114952A1 (en) | 1993-02-18 |
Family
ID=6437660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002114952A Abandoned CA2114952A1 (en) | 1991-08-03 | 1992-07-27 | Free-flowing water-containing alkyl sulfate pastes |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0596957B1 (en) |
| JP (1) | JPH06509596A (en) |
| AT (1) | ATE144278T1 (en) |
| CA (1) | CA2114952A1 (en) |
| DE (2) | DE4125792A1 (en) |
| ES (1) | ES2092690T3 (en) |
| WO (1) | WO1993003128A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ247676A (en) * | 1992-06-08 | 1995-04-27 | Colgate Palmolive Co | Anionic surfactant compositions containing alkyl sulphates as viscosity modifiers; hair shampoo |
| DE4341050A1 (en) * | 1993-12-02 | 1995-06-08 | Huels Chemische Werke Ag | Surfactant concentrates as a base side for concentrated liquid formulations |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE753752C (en) * | 1932-07-15 | |||
| GB1546127A (en) * | 1976-11-18 | 1979-05-16 | Shell Int Research | Detergent compositions |
| DE3926345A1 (en) * | 1989-08-09 | 1991-02-14 | Henkel Kgaa | AQUEOUS ANCIENT SIDE CONCENTRATES WITH A CONTENT OF OIL ACID SULPHONATES AND THE USE OF OIL ACID SULPHONATES AS A VISCOSITY CONTROLLER FOR AQUEOUS ANION ANTENSIDE CONCENTRATES |
| DE4032910A1 (en) * | 1990-10-17 | 1992-04-23 | Henkel Kgaa | Prepn. of alkyl sulphate paste with better free flow - by addn. of sulphonation prod. of unsatd. fatty acid glyceride esters to paste |
| DE4109250A1 (en) * | 1991-03-21 | 1992-09-24 | Henkel Kgaa | METHOD FOR PRODUCING HIGHLY CONCENTRATED FATTY ALCOHOL SULFATE PASTE |
-
1991
- 1991-08-03 DE DE4125792A patent/DE4125792A1/en not_active Withdrawn
-
1992
- 1992-07-27 EP EP92916262A patent/EP0596957B1/en not_active Expired - Lifetime
- 1992-07-27 DE DE59207392T patent/DE59207392D1/en not_active Expired - Lifetime
- 1992-07-27 WO PCT/EP1992/001704 patent/WO1993003128A1/en active IP Right Grant
- 1992-07-27 CA CA002114952A patent/CA2114952A1/en not_active Abandoned
- 1992-07-27 JP JP5503239A patent/JPH06509596A/en active Pending
- 1992-07-27 AT AT92916262T patent/ATE144278T1/en active
- 1992-07-27 ES ES92916262T patent/ES2092690T3/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO1993003128A1 (en) | 1993-02-18 |
| ES2092690T3 (en) | 1996-12-01 |
| JPH06509596A (en) | 1994-10-27 |
| ATE144278T1 (en) | 1996-11-15 |
| EP0596957A1 (en) | 1994-05-18 |
| DE59207392D1 (en) | 1996-11-21 |
| EP0596957B1 (en) | 1996-10-16 |
| DE4125792A1 (en) | 1993-02-04 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |