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 quaternary alkylamino-di-alkylcarboxylic acid di-esters of the formula 1 where R 1 and R 2 are alkyl or hydroxyalkyl with 1-4 C atoms or benzyl, R 3 and R 4 are hydrogen or methyl, R 5 and R 6 are alkyl or alkenyl with 8 to 24 C atoms, m and n are numbers from 1 to 4, o and p are numbers from 0 to 10, and X is a halogen, methosulfate, ethosulfate or alkyl phosphate anion.
• Preferred compounds of the formula 1 are those in which R 1 and R 2 are alkyl or hydroxyalkyl having 1 or 2 carbon atoms, R 3 and R 4 are hydrogen, R 5 and R 6 are alkyl or alkenyl having 16 to 22 carbon atoms, X Cl ⁇ , Br ⁇ or CH 3 SO 4 ⁇ , m and n 1 or 2 and o and p are numbers from 0 to 5.
• R 1 and R 2 are methyl
• R 3 and R 4 are hydrogen
• R 5 and R 6 are C 16 -C 22 alkyl
• X Cl ⁇ m and n are 1 and p and o numbers from 0 to 2 mean.
• This reaction takes place in the first stage in an inert solvent, such as benzene, toluene, xylene or a paraffinic hydrocarbon or mixtures thereof, at temperatures from about -20 ° C. to about 100 ° C.
• an inert solvent such as benzene, toluene, xylene or a paraffinic hydrocarbon or mixtures thereof.
• the dialkylamine of the formula 2 in submitted to the solvent and cooled strongly.
• the halocarboxylic acid ester of formula 3 is added and the temperature is slowly increased, in which case any excess of unreacted dialkylamine escapes.
• an appropriate one is used Excess of the dialkylamine and the resulting ammonium salt is separated off by filtration.
• the dialkylamine can be regenerated from this salt and used again.
• the dialkylaminoalkane carboxylic acid esters After distilling off the inert solvent, the dialkylaminoalkane carboxylic acid esters are obtained in a purity of over 95%. In the case of the dimethylaminoacetic acid ester, the product can also be purified by high vacuum distillation.
• dialkylaminoalkanecarboxylic acid esters are then dissolved in an alcohol or preferably dispersed in water and reacted again with a haloalkanecarboxylic acid ester of the formula 3 or 4 at temperatures below 100 ° C., preferably at 40-80 ° C.
• This reaction can also be carried out completely without any solvent.
• the pure compounds of the formula 1 are obtained.
• an aqueous dispersion is used, in which case approx. 20% aqueous dispersions of the compounds 1 are obtained, which, after further dilution with water, are used directly as fabric softeners can be used.
• Another possibility for the preparation of the compounds of formula 1 is that 1 mol of a monoalkylamine of formula 5 first reacted with 2 mol of a haloalkane carboxylic acid ester of the formula 3 or 4 and the reaction product with a compound of the formula quaternized, where Y is halogen.
• the reaction of the monoalkylamine first with the haloalkane carboxylic acid esters takes place under the same conditions as in the first stage of the process described above.
• a second amine such as triethylamine or pyridine, is used to trap the hydrogen halide formed, and the amine salt formed is also separated off by filtration.
• the ⁇ -haloalkane carboxylic acid esters of the formulas 3 and 4 serving as starting compounds can be obtained by known methods by reacting an acid of the formula or the corresponding acid chloride with an oxyalkylated alcohol of the formula
• Suitable alcohols are branched or unbranched, saturated or unsaturated alcohols with 8 to 24 carbon atoms, for example dodecyl, myristyl, cetyl, oleyl or preferably stearyl and behenyl alcohol or mixtures of these alcohols.
• the alcohol is oxalkylated in a known manner with propylene oxide or preferably ethylene oxide.
• the compounds of formula 1 according to the invention are suitable as fabric softeners and are added to the last rinsing bath in the form of aqueous dispersions with an active substance content of 1 to 15% by weight, usually 4-10% by weight of the compounds of formula 1 after washing the textile material .
• the textile material is then dried.
• These fabric softeners can also contain other substances and auxiliaries that are commonly used in fabric softeners. These include e.g. cationic or nonionic surface-active substances, electrolytes, acidifying agents, organic complexing agents, optical brightening agents or solubilizers as well as colors and fragrances.
• the products are used to additionally influence the handle of the goods or other properties of the textiles to be treated or to adjust the viscosity, regulate the pH or increase the cold stability of the solutions.
• the compounds according to the invention give any textile materials, especially those made of natural or regenerated cellulose, wool, cellulose acetate, triacetate, polyamide, polyacrylonitrile, polyester, polypropylene, a pleasant and soft feel.
• Use as a laundry aftertreatment for terry towels and underwear is particularly advantageous.
• 410 parts by weight of a chloroacetic acid ester prepared from chloroacetyl chloride and a Ziegler alcohol with a chain distribution of 60% C 20 alkyl and 40% C 22 alkyl, are dissolved in 500 parts by weight of toluene and at 20 ° C. to a solution of 220 parts by weight of dimethylamine in 250 parts by weight of toluene dripped. The mixture is stirred for 5 hours at room temperature and then for 3 hours at 70 ° C. After cooling, the precipitated dimethylamine hydrochloride is suctioned off and the solvent is removed in vacuo. 420 parts by weight of a yellowish oil are obtained.
• a chloroacetic acid ester prepared from chloroacetyl chloride and a Ziegler alcohol of chain distribution 65% C 16 alkyl and 35% C 18 alkyl, which had previously been reacted with 2 moles of ethylene oxide, were added.
• the mixture is allowed to stir in 3400 parts by weight of dest. Water with a temperature of 70 ° C flows in and stirs at this temperature for 15 hours. After this time no free amine can be found.
• the chloride content is over 95% of the expected value. A 20% white, stable, pourable dispersion is obtained.
• the compound of the formula The pure compound can be obtained in pure form by distilling off the water.
• Example 1 According to the process described in Example 1, 340 parts by weight of a chloroacetic ester from a Ziegler alcohol with 65% C 16 alkyl and 35% C 18 alkyl in 400 parts by weight of benzene are reacted with 220 parts by weight of dimethylamine in 250 parts by weight of benzene.
• Example 2 Analogously to Example 2, 495 parts by weight of a chloroacetic acid ester from an alcohol with 60% C 20 alkyl and 40% C 22 alkyl, the alcohol component of which had previously been reacted with 2 mol of ethylene oxide, 365 parts of diethylamine and another 495 parts of the same chloroacetic acid ester were reacted. Toluene is used as the solvent in the first reaction step and water in the second.
• a chloroacetic acid ester prepared from a native, hydrogenated tallow fatty alcohol with a chain distribution of 65% C 18 alkyl and 35% C 16 alkyl, are reacted analogously to Example 1 in 700 parts by weight of toluene with 220 parts by weight of dimethylamine in 250 parts of toluene. 385 parts by weight of the chloroacetic acid ester of the same tallow fatty alcohol, but previously reacted with 1 mol of ethylene oxide, serve as the quaternization component. It is quaternized in so much water that a 20% dispersion of the compound of the formula results. This compound is also isolated by distilling off the water.

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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)

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Cited By (10)

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• 1979
  • 1979-07-03 DE DE19792926772 patent/DE2926772A1/de not_active Withdrawn
• 1980
  • 1980-06-26 AT AT80103619T patent/ATE3971T1/de not_active IP Right Cessation
  • 1980-06-26 EP EP80103619A patent/EP0021431B1/fr not_active Expired
  • 1980-06-26 DE DE8080103619T patent/DE3063964D1/de not_active Expired
  • 1980-07-01 AR AR281606A patent/AR221425A1/es active
  • 1980-07-02 CA CA000355190A patent/CA1163275A/fr not_active Expired
  • 1980-07-02 JP JP8929280A patent/JPS5610153A/ja active Pending
  • 1980-07-03 BR BR8004135A patent/BR8004135A/pt unknown

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