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
  • C11D3/0005—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
  • 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 ammonium compounds of the formula 1 wherein R 1 is alkyl, 2-hydroxyalkyl or alkenyl each having 8 to 30 C atoms, R 2 C 1 -C 4 alkyl, or benzyl, A is a group of the formulas
• B has the same meaning as A and additionally a C 1 -C 4 alkylene group, RC 8 -C 30 alkyl or alkenyl, X and Y are hydrogen or methyl, where X and Y are not methyl at the same time, m 1 or 2, n is a number from 1 to 20 and A (-) is an anion.
• Preferred compounds of formula 1 are those in which R 1 is alkyl, 2-hydroxyalkyl or alkenyl each having 14-24 C atoms, R 2 is methyl, RC 14 -C 24 alkyl or alkenyl, m is a number from 1 to 5, A. (-) means a halogen, methosulfate or methophosphate ion and A, B, X, Y and m have the meaning given above.
• R 1 is C 16 -C 18 alkyl or alkenyl
• R 2 is methyl
• a and B are a group of the formula and
• a (-) represents a chloride or methosulfate ion.
• the reaction in the first stage is preferably carried out with the free fatty acid in the absence of solvents and at temperatures of approximately 130 to 180 ° C., preferably 150 to 170 ° C.
• an acid catalyst such as p-toluenesulfonic acid.
• the molar ratio of the fatty acid of formula 3 to the aminoxalkylate of formula 2 is 0.7 to 1.1, preferably 0.7 to 0.9 mol of fatty acid per 1 mol of aminoxalkylate.
• the intermediate product of formula 4 thus obtained is then dissolved in an alcohol or dispersed in water and quaternized with a compound of the above formulas in a conventional manner at temperatures below 100 ° C., preferably at 40-80 ° C.
• the compounds of formula 2 serving as starting products are known as such. They are obtained by oxyalkylating fatty alkyl amines or by reacting fatty amines with 2,3-epoxypropanol.
• suitable fatty alkylamines are dodecyl-, myristyl-, cetyl-, oleyl-, behenyl- or preferably stearylamine or mixtures of such fatty alkylamines which are derived from naturally occurring fats such as coconut oil or tallow.
• the compounds of formula 1 according to the invention are suitable as fabric softening agents and are 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 following the washing of the textile material into the last Given rinsing bath. 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, for example, cationic or nonionic surface-active substances, electrolytes, acidifying agents, organic complexing agents, optical brighteners or solubilizers as well as colorants 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 treatment agent for terry and underwear is particularly advantageous.
• 171.5 g of the compound of the formula are placed in a 500 ml flask equipped with a stirrer, nitrogen inlet, contact thermometer and descending condenser 104 g of stearic acid, 2 g of hydrazine hydrate and 2 g of p-toluenesulfonic acid are introduced under nitrogen and slowly heated to 150.degree. After an hour, the temperature is raised to 175 ° C. and maintained until the acid number is less than 6. The water of reaction released is continuously distilled off. Then allowed to cool to 70 ° C, mixed with about 112 ml of warm water and transferred to the 70 ° C warm mixture in a 1 liter autoclave.
• Example 2 120 g of the compound of the formula and 71.2 g of tallow fatty acid (molar ratio of aminoxethylate: tallow fatty acid 1: 0.8) as described in Example 1. After 7 h at 175 ° C., 179 g of ester with an acid number of 5.1 are obtained. 30 percent by weight of water are added and the 70-75 ° C. warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, gaseous methyl chloride is pressed in from a bomb at 70 - 80 ° C until a constant pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. About 270 g of a waxy mass with a solids content of 73% are obtained.
• Example 2 In an apparatus as in Example 1, 184 g. D i- (2,3-dihydroxypropyl) stearylamine and 100 g of stearic acid (molar ratio of aminoxalkylate: stearic acid 1: 0.89) are reacted as described in Example 1. After 7 h at 175 ° C., 270 g of monoesters with an acid number of 5 are obtained. About 30 percent by weight warm water is added and the 70 ° C warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, methyl chloride is pressed in gaseously from a bomb at 70 - 80 ° C until a constant pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. 400 g of a mass which is waxy at room temperature and has a solids content of 75% are obtained.
• Example 2 In an apparatus as in Example 1, 176 g of di-2-hydroxyethyl - (2-hydroxypentadecyl / octadecyl) amine and 117 g of stearic acid (molar ratio of aminoxethylate: stearic acid 1 / 0.91) are reacted as described. After 7 h at 175 ° C., 279 g of condensation product with an acid number of 6 are obtained. 30 percent by weight of warm water are added and the 70 ° C. warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, methyl chloride is pressed in from a bomb at 70-80 ° C. until a constant pressure of 5 bar is reached. Stirring is continued at 60 ° C. for two hours and the pressure is carefully released. 420 g of a mass which is waxy at room temperature and has a solids content of 72 are obtained
• Example 2 In an apparatus as in Example 1, 156 g of methyl (2,3-dihydroxypropyl) stearylamine and 91 g of stearic acid (molar ratio of aminoxalkylate: stearic acid 1: 0.88) are the same described implemented. After 7 h at 175 ° C. 225 g of ester with an acid number of 6 are obtained. 30 percent by weight of warm water are stirred in and the 70 ° C. warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, methyl chloride is pressed in gaseously from a bomb at 70 - 80 ° C until a constant pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. 360 g of a mass which is waxy at room temperature and has a solids content of 71% are obtained.
• Example 2 same end product as example 1
• R 1 tallow fatty alkyl
• R tallow fatty acyl
• R 1 mixture of 2-hydroxipentadecyl and octadecyl

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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)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Detergent Compositions (AREA)

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Publications (3)

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• 1979
  • 1979-07-14 DE DE19792928603 patent/DE2928603A1/de not_active Withdrawn
• 1980
  • 1980-07-09 US US06/167,202 patent/US4339391A/en not_active Expired - Lifetime
  • 1980-07-10 DE DE8080103954T patent/DE3070775D1/de not_active Expired
  • 1980-07-10 EP EP80103954A patent/EP0022562B1/fr not_active Expired
  • 1980-07-10 AT AT80103954T patent/ATE13879T1/de not_active IP Right Cessation
  • 1980-07-11 AR AR281737A patent/AR221651A1/es active
  • 1980-07-11 JP JP9409780A patent/JPS5618946A/ja active Granted
  • 1980-07-11 CA CA000355965A patent/CA1167054A/fr not_active Expired
  • 1980-07-11 BR BR8004336A patent/BR8004336A/pt unknown

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