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

Definitions

• the invention relates to new quaternary alkylamidobetaine esters, a process for the preparation of these new compounds and their use in textile finishing and fiber preparation or in fabric softeners.
• Quaternary alkylamidobetaine esters are known compounds.
• DE-A 16 18 026 describes compounds of the general formula below which can be prepared from the corresponding amines and halocarboxylic acid esters, wherein R ', R "and R"' are the same or different and are alkyl, alkanol, ether or amide radicals (at least one radical is a long-chain alkyl or alkenyl radical); x represents an integer from 1 to 4; Hal is halogen, especially Cl; A is derived from mono- or polyhydric alkanols.
• N-cetyl-N, N-diethylamine, lauric acid amide of N, N-dimethyl-N-aminopropylamine and sorbitol-chloropropionic acid ester are also mentioned.
• the compounds are said to have good foaming power, bactericidal activity and substantive properties.
• the object of the present invention is to synthesize new compounds which, particularly when used in fabric softening detergents, do not show the disadvantages mentioned or only show them to a lesser extent.
• R 1 , R 5 (C 14 -C 25 ) alkyl or (C 14 -C 25 ) alkenyl;
• R 2 H;
• R 3 , R 4 CH 3 or C 2 H 5 ;
• y 0 to 3 and
• x 1.
• the compounds according to the invention can also be in the form of mixtures with substituents R 1 , R 5 in each case with different numbers of C atoms; the number of carbon atoms in the substituents of the individual components of such a mixture should, however, be within the ranges claimed according to the invention.
• the ⁇ -dialkylamino (alkoxy) - propylamine-1 obtained by adding acrylonitrile to dialkylamino (alkoxy) ethanol and hydrogenating the dialkylamino (alkoxy) -1-cyanoethane formed.
• the subsequent amidation with fatty acids - also in known catfish - is carried out in particular by heating the components (amine + acid) to temperatures of more than 100 ° C. and azeotropically distilling the water formed in the reaction with an entrainer.
• fatty alcohols with monochloroacetic acid or ⁇ -monochloropropionic acid are known in the presence of a strong acid such as H 2 SO 4 or p-toluenesulfonic acid or an H ion exchanger with an entrainer such as toluene with azeotropic distillation of the Reaction water formed implemented.
• a strong acid such as H 2 SO 4 or p-toluenesulfonic acid or an H ion exchanger with an entrainer such as toluene with azeotropic distillation of the Reaction water formed implemented.
• the quaternization of the amines of the general formula (II) with the chloroalkanoic acid esters of the general formula (III) is preferably carried out in an organic solvent such as a (C 2 -C 5 ) alkanol by heating for several hours at the boiling point of the solvent, in particular between 60 and 180 ° C .
• the reaction is generally carried out (1 to 36 h) until the organically bound chlorine has been converted as completely as possible into chloride ions.
• the compounds according to the invention differ in all cases from those of the prior art (see introduction) by a long-chain alkyl or alkenyl radical R 5 which directly adjoins the carboxyl group and at y ⁇ 0 by alkoxy groups between the quaternary nitrogen and the aminopropyl radical.
• the compounds according to the invention have clearly softening properties on textiles, so that they can be used in particular in textile finishing and fiber preparation or in fabric softeners.
• these compounds do not show the disadvantages of the prior art or show them to a significantly reduced extent. This applies in particular to their particularly good solubility and dispersibility, so that they can be easily distributed even in cold rinse water.
• the compounds according to the invention are expediently used in the form of their concentrated solutions in lower alkanols, preferably isopropanol or in a mixture of these alkanols with water.
• the fabric softening agents according to the invention contain a certain amount of such lower alkanols (about 5 to 30% by weight), in particular these alkanols have 1 to 5 carbon atoms.
• a further constituent of the fabric softener can be customary nonionic dispersants or emulsifiers based on oxalkylates, which additionally contribute to the fact that the fabric softener is readily dispersible in cold water.
• Suitable nonionic dispersants are, for example, reaction products of in each case about 2 to 12 moles of ethylene oxide (EO) with an alkylphenol such as xylenol, but also with an alkylphenol with a long alkyl radical of 8 to 10 carbon atoms or with a fatty alcohol with 8 to 15 carbon atoms , in particular reaction products of about 5 to 8 moles of EO with 1 mole of alkylphenol or with 1 mole of a fatty alcohol or a mixture of such fatty alcohols.
• EO ethylene oxide
• the amount of these non-ionic compounds is 3 to 10 wt. ⁇ ⁇ at weakly concentrated fabric softeners containing the inventive compounds 10 to 30 wt .-%.
• Highly concentrated fabric softeners with a content of 30 to 70% by weight of the compounds according to the invention preferably contain 5 to 20% by weight of the nonionic dispersants.
• the addition of such dispersants is not necessary, but it can be done, for example 0.1 to 3 wt .-%.
• the more highly concentrated laundry detergents also preferably contain 5 to 30% by weight of an ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol or the (C 1 -C 4 ) alkyl ethers of these compounds. From this product group, only those compounds are considered that are liquid. These compounds have a solubilizing effect in laundry softeners.
• the fabric softener can be produced by simply mixing the components or their concentrated solutions. If necessary, perfumes, dyes, optical brighteners or other auxiliaries can also be added. To set the desired final concentration, it may be diluted with the necessary amount of water. The amounts of the individual components are chosen within the limits specified so that the sum of the components in the finished composition, including any additional amounts of water, perfumes and dyes, is 100% by weight.
• the amount of the fabric softener based on a washing machine load of laundry (approx. 4 kg), is 80 to 150 ml, 30 to 70 ml or 10 to 20 ml for a fabric softener with a compound content of 2 to 10% by weight according to the invention. , 10 to 30% by weight or 30 to 70% by weight.
• the fabric softening agents containing the compounds according to the invention can be readily dispersed in cold water without causing troublesome gel formation. It is advantageous here that they can also be input directly into household washing machines as concentrates with suitable metering devices. This good Lös - friendliness also allows them only to dilute the concentrates just before their entry into the washing machine, so that the fabric softeners may also be traded in concentrated form and not only as dilute aqueous solutions. This eliminates the need to carry large, ultimately superfluous amounts of water at all levels of the trade. " In the following examples, parts by weight ( GT ) to parts by volume (VT) behave like kg to dm 3 . Percentages are - if nothing else is specified - on the weight b e ZO gen.
• An agent made up in the concentration of one of the commercial laundry after-treatment agents contains 5% of the compound according to Example 5 of the chemical examples; the remaining content up to 100% are water, perfume, dye and emulsifier. 100 ml of this agent are added in a washing machine (4 kg capacity) in the last rinsing bath, after which the treated laundry has an excellent soft feel, comparable in size to the handle to be achieved with a commercially available fabric softener (containing distearyl-dimethylammonium chloride) is.
• An agent prepared as a fabric softener concentrate contains 20% of the compound according to Example 6; the remaining content up to 100% are water, perfume, dye and emulsifier. A result comparable to Example I is achieved with 20 ml of this agent.
• An agent prepared as a highly concentrated fabric softener contains 67% of the compound according to Example 6, 10% emulsifier (ethoxylated nonylphenol with 6 EO units), 20% diethylene glycol and 3% perfume. A result comparable to Example I is achieved from about 5 ml of this agent.

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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)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Detergent Compositions (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

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Cited By (12)

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Citations (1)

• 1985
  • 1985-02-15 DE DE19853505269 patent/DE3505269A1/de not_active Withdrawn
• 1986
  • 1986-02-08 EP EP86101631A patent/EP0192145A3/fr not_active Withdrawn
  • 1986-02-12 JP JP2701086A patent/JPS61189254A/ja active Pending
  • 1986-02-13 ES ES551940A patent/ES8705851A1/es not_active Expired
  • 1986-02-14 BR BR8600628A patent/BR8600628A/pt unknown

Patent Citations (1)

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