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
  • C11D1/38—Cationic compounds
  • C11D1/62—Quaternary ammonium 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
  • C11D1/38—Cationic compounds
  • C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with 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
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/0005—Other compounding ingredients characterised by their effect
  • C11D3/001—Softening compositions
  • C11D3/0015—Softening compositions liquid
• • 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
  • C11D3/2086—Hydroxy carboxylic acids-salts thereof

Definitions

• the invention relates to an aqueous dispersion of a compound derived from an aliphatic aminodicarboxylic acid. More particularly, the invention relates to dispersions for use as fabric softening agents.
• Fabric softeners are generally used to render textiles soft to the touch after a laundry treatment and are incorporated into commercial laundry products such as detergents, rinsing agents, and laundry drying agents.
• Representative commercial fabric softeners are, e.g., dimethyl distearyl ammonium chloride and 1-methyl-2-tallow-3-tallowamido-ethyl imidazoline methosulphate.
• the known fabric softeners have no or only very slow biodegradability and their primarily domestic wide-scale use is attended with large amounts of them entering, via the sewerage system, the city waste water and complicating its purification.
• the invention has for its object to provide compounds which are suitable for use as fabric softeners and exhibit sufficient biodegradability.
• n 1 or 2
• R1 and R2 may be the same or different and represent hydrogen, alkyl or alkenyl
• R3 and R4 may be the same or different and represent alkyl or alkenyl, such that at least 2 of the groups R1 - R4 contain 8-24 carbon atoms, at least one of the groups R1 - R4 contains 1-4 carbon atoms
• a ⁇ is the anion of a water-soluble organic Bronstedt acid, with the proviso that the acid is present in an amount more than equivalent to the amount of nitrogen compound.
• the present invention makes it possible to provide dispersions capable of rendering laundry soft to the touch which are based on amino-substituted aliphatic dicarboxylic acids of little harmfulness to the environment.
• dispersions according to the present invention in which the acid is present in at least twice the amount equivalent to the amount of amine.
• the present dispersions can be used as fabric softeners which are added separately to the laundry in the washing machine during the rinse cycle. Generally during this rinse the nitrogen compound will be present in a concentration of about 0,5 to 3 g/kg washload.
• the invention also relates to a stable aqueous dispersion of the known type mentioned in the opening paragraph, which is characterised in that the compound derived from an aliphatic aminodicarboxylic acid is a cationic nitrogen compound according to the formula given above and the Bronstedt acid is a water-soluble organic acid, the acid being added in such an amount that a dispersion diluted with mains water which contains 0,5-30 wt.% of nitrogen compound will have a pH below the value corresponding to the molar equivalence point of the nitrogen compound and the acid.
• Such a dispersion offers the assurance that there will not be any problem if a portion of the acid is inadvertently used up during the rinse cycle, e.g. as a result of scale formation on the heating elements and machine parts or because of residual detergent not removed by rinsing.
• Such a dispersion will usually have a pH of less than 5 in the concentrated form.
• the nitrogen compound and the carboxylic acid are present in such amounts that the concentrated dispersion will have a pH in the range of 1,5-3.
• the nitrogen compounds which can be employed with advantage in the present invention are based on aspartic acid and/or glutaminic acid. Preference is given to compounds based on aspartic acid, notably because of their favourable synthetic accessibility.
• the alkyl or alkenyl groups having 8-24 carbon atoms are preferably incorporated at the R3 and R4 positions, the alkyl or alkenyl groups having 1-4 carbon atoms at the R1 and R2 positions.
• the particle size, viscosity, and storage stability of the dispersions according to the invention are affected by the nature of the acid.
• citric acid malic acid, glycolic acid, and lactic acid, these being the most environment-friendly acids due to their low toxicity, favourable biodegradability, and low aquatoxicity.
• the acid held to be most suitable in this respect is citric acid.
• the invention also provides for the use of a mixture of acids. This is not only the case when a combination of properties is advisable, but also because the use of different acids makes it possible to set the viscosity and the degree of acidity of the dispersions as desired.
• the particle size, viscosity, and storage stability of the dispersions according to the present invention can be affected by means of dispersing agents, preferably ethoxylated fatty amines and fatty alcohols.
• dispersing agents preferably ethoxylated fatty amines and fatty alcohols.
• examples of such dispersing agents are those available under Akzo Chemicals registered trade mark names Ethomeen and Elfapur.
• the invention further relates to fabric softening agents comprising a quaternary ammonium compound derived from aspartic and/or glutaminic diesters.
• the quaternary ammonium compounds according to the present invention satisfy the following formula: wherein n equals 1 or 2, R5 - R8 may be the same or different and represent alkyl or alkenyl, such that at least two of these groups contain 8-24 carbon atoms and at least one of these groups contains 1-4 carbon atoms, Q is an alkyl or hydroxy alkyl group containing 1-6 carbon atoms, and X ⁇ is an anion.
• Quaternary ammonium compounds are known in themselves in the field of fabric softeners and no further elucidation is required for the skilled man. It is preferred that Q is methyl and X ⁇ is a halide ion, preferentially Cl ⁇ , or CH3SO4 ⁇ . Unlike the compounds known from US 4 026 915, the quaternary ammonium compounds according to the present invention are readily biodegradable. Also for the quaternary ammonium compounds it holds that the aforementioned prejudice set forth in said US patent specification is not likely to encourage the skilled man to employ the present simple aspartic or glutaminic acid derivatives in fabric softening agents.
• the invention further relates to compounds which are favoured for use in fabric softening compositions and satisfy the following formula: wherein n equals 1 or 2, R9 and R10 may be the same or different and represent hydrogen, an alkyl or alkenyl group having 1-4 carbon atoms, and R11 and R12 may be the same or different and represent an alkyl or alkenyl group having 8-24 carbon atoms.
• the preparation of amino compounds which can be used as starting material for the cationic nitrogen compounds according to the present invention may, int. al., be carried out by making use of an unsaturated dicarboxylic ester, e.g. dihydrogenated tallow maleate, and then reacting it with an amine.
• an unsaturated dicarboxylic ester e.g. dihydrogenated tallow maleate
• Such a preparative process as well as the preparation of the diester may be carried out analogous to the description in the aforementioned US patent specification.
• the same product may also be obtained without solvent by reacting 689 g (1,15 moles) of molten dihydrogenated tallow maleate and 91 ml (1,38 moles) of gaseous dimethylamine in the autoclave at a temperature of 110°-120°C. Decreasing the dimethylamine to the equimolar amount caused a decrease of the base number by 3%.
• the N,N-dimethyl dihydrogenated tallow aspartate was converted to its cationic form through the addition of 5 wt.% of the N,N-dimethyl dihydrogenated tallow aspartate to a solution of 5 wt.% of citric acid monohydrate and 1 wt.% of Elfapur® LM75S in demineralized water heated, with stirring, to 60°C and subsequently cooled, with stirring, to 20°C.
• the pH value of the undiluted dispersion was 2,1.
• the dispersion was found to have favourable fabric softening properties.
• Biodegradability was tested in accordance with the EEC/OECD guidelines, using the so-called “Closed Bottle Test".
• the present cationic nitrogen compound was found to meet the requirements for being designated readily biodegradable, which means biodegradation of at least 60% within 28 days.

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• 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)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

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Publications (2)

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Cited By (5)

Citations (5)

• 1991
  • 1991-11-14 EP EP19910202966 patent/EP0486113A3/en not_active Ceased
  • 1991-11-15 JP JP32671891A patent/JPH04289271A/ja active Pending

Patent Citations (5)

Non-Patent Citations (1)

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