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
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
  • D06M13/46—Compounds containing quaternary nitrogen atoms
  • D06M13/467—Compounds containing quaternary nitrogen atoms derived from polyamines

Definitions

• the invention relates to quaternary esters of hydroxyalkylamidoamines having the general formula 1.
• R 1 and P 3 are alkyl or alkenyl with 7 to 24 C atoms, R 2 alkyl or hydroxyalkyl with 1 to 4 C atoms or benzyl, R 4 is hydrogen or methyl, R 5 is hydrogen or alkyl with 1 to 6 C atoms , m 2 or 3, n is a number from 1 to 8 and X is a halogen, alkyl sulfate or alkyl phosphate anion.
• R 1 and R 3 are alkyl having 15 to 22 carbon atoms
• R 2 is methyl
• R 4 is hydrogen
• R 5 is hydrogen or methyl
• m 3 is a number from 1 to 3
• X. is a chloride or methosulfate anion.
• These compounds are prepared by first using a diamine of the general formula 2 in an equimolar amount with a carboxylic acid of the general formula 3 implements.
• the resulting amidoamine of Formula 4 is in the second reaction step with an alkylene oxide of formula 5 to the hydroxyalkylamidoamine of the formula 6 implemented.
• This compound is esterified with a fatty acid R 3 COOH and reacted in the last step with an alkylating agent of the formula R 2 X to the quaternary esters according to the invention.
• the reaction of the diamine (2) in the first stage with the carboxylic acid (3) is carried out in an inert solvent or, preferably, in bulk at temperatures from 120 to 200 ° C., preferably at 140 to 180 ° C. with simultaneous removal of the water of reaction formed. It goes without saying that derivatives such as acid chlorides or acid anhydrides can also be used instead of the free acids. The complete course of the reaction is controlled via the acid number.
• the resulting amidoamines (4) are in a known manner with an alkylene oxide such as ethylene oxide or propylene oxide, mixtures of these two or with both agents successively, but preferably with ethylene oxide alone to the Hydroxialkylamidoaminen (6).
• an alkylene oxide such as ethylene oxide or propylene oxide
• the esterification of the hydroxiamidoamines (6) is carried out by known methods in higher-boiling inert solvents such as toluene or xylene or preferably in bulk with stoichiometric or slightly sub-stoichiometric amounts of a fatty acid R 3 COOH.
• the reflux temperature of the reaction mixture is expediently chosen as the reaction temperature and the water of reaction formed is removed azeotropically.
• the water of reaction is distilled off directly from the reaction mixture.
• the reaction temperatures here are 140 to 220 ° C, preferably 150 to 180 ° C.
• An acid catalyst such as p-toluenesulfonic acid is used to accelerate the reaction. The completeness of the reaction is checked by determining the acid number.
• esters of hydroxyalkylamidoamines thus obtained are then dissolved in an alcohol or, preferably, dispersed in water and reacted with an alkylating agent R 2 X at temperatures below 100 ° C., preferably at 40 to 80 ° C., to give the quaternary products according to the invention.
• This reaction can also be carried out without any solvent.
• the pure compounds of the formula (1) are obtained.
• the process is carried out in aqueous dispersion, with 20% aqueous dispersions of the compounds (1) being obtained directly, which, after appropriate dilution with water and preparation, can be used directly as fabric softener.
• Diamines of the formula (2) used with preference are the industrially available products tallow fat propylene diamine or stearyl propylene diamine. But it is according to the inven It is equally possible to use other diamines with a more or less wide alkyl chain distribution. Such diamines are produced in a known manner by adding acrylonitrile to primary fatty amines and then catalytically hydrogenating the propionitriles. For the amidation with the carboxylic acid 3, formic acid or acetic acid is preferably used.
• Fatty acids suitable for esterification are natural or synthetic products such as Palmitic acid, stearic acid, behenic acid or branched chain compounds from oxo synthesis such as e.g. Isostearic acid or mixtures of the ones mentioned, e.g. accrued from natural cuts derived from coconut oil or tallow.
• the alkylating agent used is preferably methyl chloride or dimethyl sulfate.
• the crfindungsdorfen compounds of formula (1) are suitable as a laundry Weichs p ülstoff and be in the form of aqueous dispersions with an active substance content of 1 to 15 wt .-%, usually 4 - 10 wt .-% of compounds of formula 1 following the wash the textile material in the last 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 from 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.
• the mixture is stirred at 140 ° C. for 2 hours and allowed to cool.
• a medium-strong nitrogen stream is passed through the reaction mixture at 50 ° C. under vacuum for 1 hour.
• 235 g of pourable, viscous product are obtained, which is transferred to a glass flask.
• 122 g (0.45 mol) of technical stearic acid, 0.3 g of p-toluenesulfonic acid and 0.25 g of hydrazine hydrate are added and the mixture is heated to 170 ° C. with a blanket of nitrogen. Water distills off via a descending cooler. After four hours of stirring at 170 ° C., the acid number is less than 5.
• Example 1 The procedure described in Example 1 is followed with the following amounts: To simplify matters, the entire synthesis can be carried out in an autoclave. In this case, devices for dropping and distilling off must be attached during the condensation steps.
• A statistical mixture of 1 mol -CH 2 -CH 2 -O- and 0.7 mol

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• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Textile Engineering (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (3)

• 1979
  • 1979-09-07 DE DE19792936121 patent/DE2936121A1/de not_active Withdrawn
• 1980
  • 1980-08-26 EP EP19800105053 patent/EP0025165A1/fr not_active Withdrawn
  • 1980-09-02 ES ES494707A patent/ES494707A0/es active Granted
  • 1980-09-05 JP JP12244180A patent/JPS5645446A/ja active Pending
  • 1980-09-05 AR AR28242280A patent/AR221961A1/es active
  • 1980-09-05 BR BR8005664A patent/BR8005664A/pt unknown

Patent Citations (3)

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