EP0662510B1 - Hydrotrope Mittel und diese Mittel enthaltende Zusammensetzungen - Google Patents

Hydrotrope Mittel und diese Mittel enthaltende Zusammensetzungen Download PDF

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Publication number
EP0662510B1
EP0662510B1 EP95420002A EP95420002A EP0662510B1 EP 0662510 B1 EP0662510 B1 EP 0662510B1 EP 95420002 A EP95420002 A EP 95420002A EP 95420002 A EP95420002 A EP 95420002A EP 0662510 B1 EP0662510 B1 EP 0662510B1
Authority
EP
European Patent Office
Prior art keywords
hydrotropic
weight
agents
solution
product
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
EP95420002A
Other languages
English (en)
French (fr)
Other versions
EP0662510A1 (de
Inventor
Lionel Godefroy
Paul Nivollet
Wolfgang Schwiening
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.)
Stepan Europe SAS
Original Assignee
Stepan Europe SAS
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 Stepan Europe SAS filed Critical Stepan Europe SAS
Publication of EP0662510A1 publication Critical patent/EP0662510A1/de
Application granted granted Critical
Publication of EP0662510B1 publication Critical patent/EP0662510B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • 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
    • C11D1/143—Sulfonic 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
    • 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
    • C11D1/16—Sulfonic acids or sulfuric acid esters; Salts thereof derived from divalent or polyvalent alcohols

Definitions

  • the present invention belongs to the field of surfactant detergents and relates more particularly hydrotropic agents intended to allow the formulation in high concentration of the detergents.
  • tensioactivity is meant the property of a product in solution of lowering the tension interfacial associated with an increase in the concentration of the product at the interface.
  • Hydrotropy means the property of a product to increase the solubility of a substance in water, without this product being a soil solvent. This property will be particularly exploited in the invention for solubilizing high concentrations of surfactant detergents in water.
  • a hydrotropic agent may also have tensloactive properties.
  • the concentrated formulations of agents are advantageous for the user, because they are more economical, less bulky, less heavy to carry. This applies equally well to liquid preparations, whether they are monophasic or multiphase, than solid preparations generally prepared from multiphase liquid preparations very concentrated.
  • the formulator has at its disposal a certain number of adjuvants among which are the stabilizing dispersing agents, and the solubilizing or hydrotropic agents.
  • a good hydrotropic agent should not only dissolve the detergent in water when it is in it. high concentrations, but it must also stabilize the formulation obtained, and this at temperatures fairly low, when the use makes it necessary.
  • solubilizing agents In addition to their hydrotropic nature, solubilizing agents must meet regulatory standards concerning their toxicity and their biodegradability, as well as the wishes of users concerning in particular the impact of these agents on the environment. Thus, these agents must be little or not harmful for man and the environment, not bioaccumulative. biodegradable, non-volatile and must not release resistant by-products.
  • hydrotropic agents there are solvents of the alcohol type, arylsulfonates. low molecular weight, such as benzene sulfonates, tuuene sulfonates, xylenesulfonates, cumenesulfonates, as well as short carbon chain alcohol sulfates, preferably with 8 atoms of carbon.
  • Alcoholic solvents are mostly volatile and fall into the category of VOCs (Volatile Organic Compound) likely by their volatility to contribute to the reduction of the ozone content and to the effect Greenhouse. They are also easily flammable.
  • VOCs Volatile Organic Compound
  • Aryl sulfonates due to the presence of aromatic rings in their structure, are assumed lead to relatively persistent by-products harmful to the aquatic environment. Finally the alcohol sulfates are easily hydrolyzable and therefore of more limited use.
  • Such agents are preferably presented in liquid form, which requires dilution. important for their implementation, which is penalizing economically.
  • the object of the present invention is a hydrotropic agent which on the one hand has good solubility in water and excellent hydrotropy, but which on the other hand is non-volatile and completely biodegradable.
  • This hydrotropic agent which exerts in particular its effect on the detergent surfactant compounds, which they be anionic, nonionic or amphoteric, has moreover surfactant properties which come complete those of the solubilized surfactant compound, which from an economic point of view is not negligible.
  • the hydrotropic agent is identical to the product capable of being obtained according to the method of Example 1, or 2, or 3 below.
  • Hydrotropic agents meeting the definition of the present invention have a solubilizing power often higher than that of arylsulfonates commonly used today, and therefore provide access to new presentations of even more concentrated detergent compositions.
  • the hydrotropic agents of the invention obtained by the specific mixture described above, have, in the same conditions, greater solubility, easier commercial presentation, or more concentrated, for an identical cold resistance, therefore more economical, and confer better stability of the preparations resulting at low temperature.
  • Another subject of the invention is a detergent composition
  • a detergent composition comprising a surfactant compound and a hydrotropic agent of said surfactant, in accordance with the invention.
  • hydrotropic agents of the invention give the compositions containing them a better resistance to crystallization, under the effect of lowering the temperature, and have a low power foaming, which allows easy handling.
  • these agents have good resistance to hydrolysis, in a wide pH range, and a good resistance to oxidizing products such as hypochlorites for example.
  • Examples 1 to 4 illustrate the characteristics and advantages of the present invention, in which Examples 1 to 3 illustrate the methods for obtaining the hydrotropic agents of the invention and Example 4 illustrates compositions of the invention.
  • solution B After 30 minutes of reflux, 5% by weight of solution B are introduced into the first reactor and waits until the pH rises to 8, while keeping the latter between 7 and 8.
  • the sulfur dioxide is introduced as slowly as possible and the pH is stabilized around 5.5-6.
  • the dry matter content is determined by the conventional dry matter measurement technique, placing in the present case 3 g of the product obtained for 6 hours in an oven of 105 ° C. Dry matter determined at 43% is adjusted by adding water.
  • H 2 O 2 is treated with 130 volumes if necessary so that the sodium sulfite content is less than 0.1%.
  • product 1 contains at least 25% by weight of octyl-1-sulfonate constituting the majority fraction, and from 5 to 10% by weight of octyl-disulfonate.
  • solution B After 30 minutes of reflux, 5% by weight of solution B is introduced into the first reactor and waits for the pH to rise to 8 while keeping the pH between 7 and 8.
  • the sulfur dioxide is then introduced as slowly as possible and the pH is stabilized around 5.5-6.
  • Dry matter determined at 43% (by the same conventional measurement technique, 3 g for 6 hours at 105 ° C) is adjusted by adding water.
  • H 2 O 2 130 volumes are treated so that the sodium sulfite content is less than 0.1%.
  • product 2 About 100 g of product 2 are finally obtained and which contain at least 25% by weight of alkyl (C 6 and C 8 ) -1-sulfonate and from 5 to 10% by weight of alkyl (C 6 and C 8 ) - disulfonate.
  • the mixture is heated with stirring while maintaining at reflux at 55 ° C.
  • solution B is introduced into the first reactor and brings the temperature to 75-80 ° C (therefore under pressure) until the pH rises to 8 while maintaining the latter between 7 and 8.
  • the sulfur dioxide is then introduced as slowly as possible and the pH is stabilized around 5.5-6,
  • Dry matter determined at 43% (by the classic measurement technique, 3 g for 6 hours at 105 ° C) is adjusted by adding water.
  • H 2 O 2 is treated with 130 volumes so that the sodium sulfite content is less than 0.1%.
  • product 3 which contain at least 25% by weight of hexyl-1-sulfonate constituting the majority fraction, and from 5 to 10% by weight of sodium hexyl disulfonate.
  • Product 2 obtained according to the process described in Example 2 can be prepared by mixing products 1 and 3 .
  • the following example relates to formulations such as cleaning products and provides the necessary concentrations of hydrotropic compound to obtain homogeneous formulations (without phase solid) at a defined temperature provided.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (2)

  1. Hydrotropes Mittel, insbesondere tensioaktive Detergenszusammensetzungen, welches Alkylsulfonate aufweist, dadurch gekennzeichnet, daß das Mittel gleich einem Erzeugnis ist, das nach dem Verfahren von Beispiel 1 oder 2 oder 3 erhältlich ist.
  2. Detergenssusammensetzung, die ein tensioaktives Mittel aufweist, dadurch gekennzeichnet, daß diese Zusammensetzung außerdem ein hydrotropes Mittel nach Anspruch 1 aufweist.
EP95420002A 1994-01-06 1995-01-05 Hydrotrope Mittel und diese Mittel enthaltende Zusammensetzungen Expired - Lifetime EP0662510B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9400229 1994-01-06
FR9400229A FR2714674B1 (fr) 1994-01-06 1994-01-06 Agents hydrotropes et compositions les contenant.

Publications (2)

Publication Number Publication Date
EP0662510A1 EP0662510A1 (de) 1995-07-12
EP0662510B1 true EP0662510B1 (de) 2002-06-12

Family

ID=9458928

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95420002A Expired - Lifetime EP0662510B1 (de) 1994-01-06 1995-01-05 Hydrotrope Mittel und diese Mittel enthaltende Zusammensetzungen

Country Status (4)

Country Link
EP (1) EP0662510B1 (de)
DE (1) DE69526987T2 (de)
ES (1) ES2176301T3 (de)
FR (1) FR2714674B1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1228113A (zh) * 1996-06-28 1999-09-08 普罗格特-甘布尔公司 含有二阴离子或烷氧基化二阴离子表面活性剂的液体清洗组合物和洗发剂
US5958858A (en) * 1996-06-28 1999-09-28 The Procter & Gamble Company Low anionic surfactant detergent compositions

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2090290A1 (de) * 1970-05-26 1972-01-14 Texaco Trinidad
FR2099203A5 (de) * 1970-06-18 1972-03-10 Texaco Trinidad

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1254798B (de) * 1964-06-26 1967-11-23 Henkel & Cie Gmbh Fluessige oder pastenfoermige Waschmittelkonzentrate
BE787231A (fr) * 1971-08-05 1973-02-05 Texaco Trinidad Composition detergente
DE3447859A1 (de) * 1984-12-31 1986-07-10 Henkel KGaA, 4000 Düsseldorf Verwendung von alkansulfonaten als viskositaetsregler fuer hochviskose aniontensid-konzentrate
EP0616027A1 (de) * 1993-03-19 1994-09-21 The Procter & Gamble Company Konzentrierte Reinigungszusammensetzungen

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2090290A1 (de) * 1970-05-26 1972-01-14 Texaco Trinidad
FR2099203A5 (de) * 1970-06-18 1972-03-10 Texaco Trinidad

Also Published As

Publication number Publication date
EP0662510A1 (de) 1995-07-12
DE69526987D1 (de) 2002-07-18
FR2714674A1 (fr) 1995-07-07
ES2176301T3 (es) 2002-12-01
FR2714674B1 (fr) 1996-03-15
DE69526987T2 (de) 2003-02-20

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