EP0108321B1 - Utilisation de composés organiques à faible poids moléculaire comme régulateurs de viscosité pour concentrés techniques tensio-actifs à haute viscosité - Google Patents
Utilisation de composés organiques à faible poids moléculaire comme régulateurs de viscosité pour concentrés techniques tensio-actifs à haute viscosité Download PDFInfo
- Publication number
- EP0108321B1 EP0108321B1 EP83110590A EP83110590A EP0108321B1 EP 0108321 B1 EP0108321 B1 EP 0108321B1 EP 83110590 A EP83110590 A EP 83110590A EP 83110590 A EP83110590 A EP 83110590A EP 0108321 B1 EP0108321 B1 EP 0108321B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- concentrates
- viscosity
- viscosity regulators
- compounds
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- 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
-
- 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
-
- 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
-
- 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
- C11D3/2068—Ethers
-
- 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
- C11D3/2075—Carboxylic acids-salts 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
- C11D3/2082—Polycarboxylic acids-salts 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/33—Amino carboxylic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
- Y10S516/04—Protein or carboxylic compound containing
Definitions
- aqueous slurries which contain a large part of the detergent constituents or also all detergent constituents. From an economic point of view, it is important that the slurry is as rich as possible in detergent components, i.e. is as low in liquid fiber as possible. The lowest possible amount of water is therefore used to prepare the slurries. Concentration is limited by the highest possible viscosity at which the slurry can just be processed.
- anionic surfactants which are mostly used as paste-like concentrates in the form of their alkali or ammonium salts in the production of the detergent slurries.
- the surfactant content of technical concentrates is approx. 30% by weight. Pastes with a higher surfactant content can no longer be processed.
- a special feature of the rheological behavior of surfactant concentrates is that they do not react to the addition of water with a reduction in viscosity, but first with a thickening to a gel-like state, which poses further problems for the processor. For example, it is often not easy to get gel clumps back into solution, or valves on pumps and containers become blocked.
- DE-OS 2251 405 describes the salts of certain carboxylic acids, in particular hydroxycarboxylic acids, as viscosity regulators.
- sulfonated aromatic compounds are suitable for these purposes.
- DE-OS 2326006 mentions sulfates or sulfonates of aliphatic, optionally substituted hydrocarbons as viscosity regulators. The addition of lower alkanols is also listed as a possibility for reducing the viscosity in the publications mentioned.
- hydrotropes such as cumene sulfonate or acidic phosphoric acid esters (DE-AS 1617160) or of polyhydric alcohols, certain carboxylic acids and / or esters of these compounds is described (EP-OS 8060). From European published application No. 24711 it is known to add sulfates of certain polyalkyl ether glycols to improve the flow behavior of anionic surfactant concentrates.
- the object of the present invention is therefore to provide substances for improving the flow behavior of aqueous technical anionic surfactant concentrates, in particular of a-sulfofatty acid esters, so that they can be processed in higher concentrations than before or have no increase in viscosity when diluted with water.
- surfactant content can be adjusted to approximately 60% by weight in the industrial manufacture of the surfactant concentrates without the viscosity exceeding the upper limit of about 10,000 mPas permissible for processability , whereby surfactant concentrates with lower water ballast are obtained.
- these concentrates are diluted, the temporary increase in viscosity which is otherwise observed does not occur, which is also advantageous for processing.
- the viscosity regulators are preferably added to the aqueous industrial anionic surfactant concentrates in amounts of approximately 10% by weight, ie in particular 7-12% by weight, based on the surfactant stop, whereby the desired viscosity reduction of the concentrate is determined by the amounts of the viscosity regulator added.
- the compounds suitable as viscosity regulators are derived, for example, from acetic acid, succinic acid or malonic acid.
- the sodium salts of the compound mentioned are particularly suitable.
- Examples of the compounds mentioned are the sodium salts of monochloroacetic acid, a-sulfosuccinic acid, a-sulfomalonic acid, a-sulfoacetic acid, a-sulfoacetic acid methyl ester, cyanoacetic acid and also cyanoacetic acid ethyl ester.
- the compounds mentioned can be added individually or in a mixture.
- the viscosity-reducing effect is particularly pronounced at low pH values, for example at pH values below 7. In some cases, this is a further advantage of the use of the compounds mentioned according to the invention.
- the addition of other compounds with electron-withdrawing groups also reduces the viscosity of anionic surfactant concentrates; Examples of such compounds are the sodium salts of vinyl sulfonate and nitrilotriacetic acid.
- Dipropylene glycol monomethyl ether is also suitable as a viscosity regulator.
- This type d) compound of the aforementioned viscosity regulators is an ether alcohol which contains two propylene glycol units and a methoxy group.
- Viscosity regulation is a particular problem for concentrates of a-sulfofatty acid esters, since concentrates with a surfactant content of more than about 30% by weight are no longer easy to process. Without the viscosity problem, it would be technically possible to produce surfactant concentrates with up to about 80% by weight of surfactant. The reduction in viscosity of a-sulfofatty acid ester concentrates is therefore a particular object of the present invention.
- the a-sulfofatty acid esters to the concentrates of which the viscosity regulators mentioned are added, are derived from fatty acids with 10 to 20, preferably 12 to 18, carbon atoms and from aliphatic alcohols with 1 to 10, preferably 1 to 4, carbon atoms in the molecule.
- the sulfo group is introduced either by sulfonation of the fatty acid and subsequent esterification of the carboxyl group with alcohol or by sulfonation of a corresponding fatty acid ester. According to both methods, esters of sulfo fatty acids are obtained which contain the sulfo acid group in the a position.
- Particularly suitable a-sulfofatty acid esters are the alkali or ammonium salts of the ethyl and especially the methyl ester of tallow fatty acid with a sulfo group in the a-position, the acid component of the fatty acid esters consisting essentially of saturated Cw and C, 8 fatty acids.
- the salts are prepared by neutralizing the acidic esters with the appropriate bases.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Claims (5)
comme régulateurs de viscosité pour concentrés technique de tensioactifs à haute viscosité du type des tensioactifs anioniques synthétiques, en particulier d'esters d'a-sulfoacides gras avec au moins 30% en poids du sel sodique de l'ester d'a-sulfoacide gras, avec addition du régulateur de viscosité en des quantités de 1 à 15% en poids par rapport à la quantité de tensioactif, pour que se produise une diminution de la viscosité des concentrés jusqu'à atteindre au plus 10000 mPas à 70°C.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT83110590T ATE27175T1 (de) | 1982-11-02 | 1983-10-24 | Verwendung von niedermolekularen organischen verbindungen als viskositaetsregler fuer hochviskose technische tensid-konzentrate. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19823240403 DE3240403A1 (de) | 1982-11-02 | 1982-11-02 | Verwendung von niedermolekularen organischen verbindungen als viskositaetsregler fuer hochviskose technische tensid-konzentrate |
DE3240403 | 1982-11-02 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0108321A2 EP0108321A2 (fr) | 1984-05-16 |
EP0108321A3 EP0108321A3 (en) | 1985-03-20 |
EP0108321B1 true EP0108321B1 (fr) | 1987-05-13 |
Family
ID=6177093
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP83110590A Expired EP0108321B1 (fr) | 1982-11-02 | 1983-10-24 | Utilisation de composés organiques à faible poids moléculaire comme régulateurs de viscosité pour concentrés techniques tensio-actifs à haute viscosité |
Country Status (6)
Country | Link |
---|---|
US (1) | US4532076A (fr) |
EP (1) | EP0108321B1 (fr) |
JP (1) | JPS5998187A (fr) |
AT (1) | ATE27175T1 (fr) |
BR (1) | BR8305985A (fr) |
DE (2) | DE3240403A1 (fr) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8405266D0 (en) * | 1984-02-29 | 1984-04-04 | Unilever Plc | Detergent compositions |
DE3804609A1 (de) * | 1988-02-13 | 1989-08-24 | Henkel Kgaa | Verfahren zur herstellung niedrigviskoser estersulfonatpasten |
DE3827778A1 (de) * | 1988-08-16 | 1990-02-22 | Henkel Kgaa | Pastenfoermiges wasch- und reinigungsmittel und verfahren zur herstellung |
US5152932A (en) * | 1989-06-09 | 1992-10-06 | The Procter & Gamble Company | Formation of high active detergent granules using a continuous neutralization system |
US5429773A (en) * | 1993-02-05 | 1995-07-04 | The Procter & Gamble Company | Process to improve alkyl ester sulfonate surfactant compositions |
FR2989093B1 (fr) * | 2012-04-06 | 2014-04-18 | Total Sa | Composes tensio-actifs, compositions en comportant, procede de synthese et utilisations, notamment pour la recuperation assistee d'hydrocarbures |
CN113403053B (zh) * | 2020-03-16 | 2022-11-18 | 中国石油化工股份有限公司 | 一种油溶性稠油降粘剂 |
Family Cites Families (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2195187A (en) * | 1938-09-12 | 1940-03-26 | Solvay Process Co | Production of sulphonation derivatives |
NL292581A (fr) * | 1961-03-01 | |||
US3151084A (en) * | 1961-03-13 | 1964-09-29 | Swift & Co | Solubilizer for synthetic detergent |
DE1218646B (de) * | 1963-07-13 | 1966-06-08 | Henkel & Cie Gmbh | Fluessige oder pastenfoermige Waschaktivsubstanzkonzentrate |
US3345301A (en) * | 1963-10-23 | 1967-10-03 | Henkel & Cie Gmbh | Pourable and free-flowing detergent, wetting, and emulsifying compositions |
DE1225799B (de) * | 1964-01-10 | 1966-09-29 | Henkel & Cie Gmbh | Fluessige oder pastenfoermige, seifenhaltige Waschaktivsubstanzkonzentrate |
DE1254798B (de) * | 1964-06-26 | 1967-11-23 | Henkel & Cie Gmbh | Fluessige oder pastenfoermige Waschmittelkonzentrate |
US3338838A (en) * | 1964-11-17 | 1967-08-29 | Procter & Gamble | Detergent composition |
NO121968C (fr) * | 1966-06-23 | 1977-06-13 | Mo Och Domsjoe Ab | |
US3882038A (en) * | 1968-06-07 | 1975-05-06 | Union Carbide Corp | Cleaner compositions |
DK129804A (fr) * | 1969-01-17 | |||
BE790362A (fr) * | 1971-10-20 | 1973-02-15 | Albright & Wilson | Composants de detergents |
JPS5139248B2 (fr) * | 1971-12-29 | 1976-10-27 | ||
BE795095A (fr) * | 1972-02-07 | 1973-05-29 | Albright & Wilson | Concentrat aqueux pouvant etre utilise comme composant detergent |
GB1437089A (en) * | 1972-05-26 | 1976-05-26 | Albright & Wilson | Detergent concentrates |
CA995092A (en) * | 1972-07-03 | 1976-08-17 | Rodney M. Wise | Sulfated alkyl ethoxylate-containing detergent composition |
DE2243306A1 (de) * | 1972-09-02 | 1974-03-21 | Henkel & Cie Gmbh | Schaumregulierte waschmittel, insbesondere fuer trommelwaschmaschinen |
US3914185A (en) * | 1973-03-15 | 1975-10-21 | Colgate Palmolive Co | Method of preparing liquid detergent compositions |
US4061586A (en) * | 1973-04-09 | 1977-12-06 | Colgate-Palmolive Company | Olefin sulfonate detergent compositions |
US4107095A (en) * | 1973-04-11 | 1978-08-15 | Colgate-Palmolive Company | Liquid olefin sulfonate detergent compositions containing anti-gelling agents |
US4003857A (en) * | 1973-12-17 | 1977-01-18 | Ethyl Corporation | Concentrated aqueous olefins sulfonates containing carboxylic acid salt anti-gelling agents |
US3971815A (en) * | 1974-11-13 | 1976-07-27 | The Procter & Gamble Company | Acid mix process |
US4203873A (en) * | 1975-12-23 | 1980-05-20 | Agency Of Industrial Science & Technology | Anionic detergent composition containing a builder mixture comprising an imidobis-sulfate and sodium citrate or nitrilotriacetate |
DE2834073A1 (de) * | 1978-08-03 | 1980-02-28 | Basf Ag | Verwendung von mehrwertigen alkoholen, (hydroxy)carbonsaeuren und/oder deren estern mit den mehrwertigen alkoholen als viskositaetsregler |
JPS5587759A (en) * | 1978-12-26 | 1980-07-02 | Lion Corp | Preparation of homogeneous aqueous solution of alpha-olefinsulfonate |
EP0024711B2 (fr) * | 1979-09-01 | 1989-02-08 | Henkel Kommanditgesellschaft auf Aktien | Produits concentrés de tensides aqueux et procédé pour l'amélioration des propriétés d'écoulement de produits concentrés de tensides aqueux difficilement transportables |
JPS57180699A (en) * | 1981-04-30 | 1982-11-06 | Lion Corp | Granular detergent composition |
US4414128A (en) * | 1981-06-08 | 1983-11-08 | The Procter & Gamble Company | Liquid detergent compositions |
DE3151679A1 (de) * | 1981-12-28 | 1983-07-07 | Henkel KGaA, 4000 Düsseldorf | "verwendung von viskositaetsreglern fuer tensidkonzentrate" |
-
1982
- 1982-11-02 DE DE19823240403 patent/DE3240403A1/de not_active Withdrawn
-
1983
- 1983-10-19 US US06/543,672 patent/US4532076A/en not_active Expired - Fee Related
- 1983-10-24 DE DE8383110590T patent/DE3371538D1/de not_active Expired
- 1983-10-24 EP EP83110590A patent/EP0108321B1/fr not_active Expired
- 1983-10-24 AT AT83110590T patent/ATE27175T1/de not_active IP Right Cessation
- 1983-10-31 BR BR8305985A patent/BR8305985A/pt not_active IP Right Cessation
- 1983-11-02 JP JP58206819A patent/JPS5998187A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
DE3371538D1 (en) | 1987-06-19 |
BR8305985A (pt) | 1984-06-05 |
JPS5998187A (ja) | 1984-06-06 |
US4532076A (en) | 1985-07-30 |
ATE27175T1 (de) | 1987-05-15 |
EP0108321A2 (fr) | 1984-05-16 |
DE3240403A1 (de) | 1984-05-03 |
EP0108321A3 (en) | 1985-03-20 |
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