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
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
  • C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
  • C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D233/14—Radicals substituted by oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
  • C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
  • C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D233/16—Radicals substituted by nitrogen atoms
• • 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

Definitions

• washed textiles especially those of cellulosic fibers, show a hardening of the handle after drying. This is especially the case when washing has been effected on a washing machine.
• imidazolinium compounds which are fluid as concentrated solutions can be used as softeners for textile materials.
• These imidazolinium compounds are, for example, l-alkylamido-ethyl-2-alkyl-3- methyl 3 methyl-imidazolinium-methosulfates, whose softening effect is much lower than that of dialkyl-dimethyl-ammonium salts.
• the present invention provides imidazolinium compounds of the general formula I in which R represents alkyl or alkenyl of about 7 to 21 carbon atoms, R represents alkyl or alkenyl of about 6 to 18 carbon atoms, of which radicals R and R at least one contains more than 14 carbon atoms, R represents a methyl or ethyl radical, X represents oxygen or the radical -NH and A represents a saft-forming anion, in particular Cl or -R -OSO
• the present invention furtermore relates to fluid concentrates of softeners for textiles which consist essentially of about to 80% by weight, preferably to by weight, of an imidazolinium salt of the above-specified general formula I in a polar organic solvent.
• polar organic solvents for the preparation of the concentrates of softeners for textiles there may be used above all lower aliphatic alcohols or glycols, in particular ethanol, isopropanol, isobutanol, ethylene glycol, propylene glycol or polyethylene glycols which are liquid at room temperature.
• the imidazolinium compounds on which the softeners of the invention are based may be prepared by the condensation of 1 mole of a long chain aliphatic carboxylic acid of the formula in which R has the meaning given above, with about 1 to 1.1 mole of diethylene-triamine or N-oxyethyl-ethylene diamine in known manner and further reaction of the condensation product with about 1 to 1.2 moles of a 1,2- epoxy-alkane of the formula CHz-CH-Rr in which R has the formula given above.
• the reaction is carried out by melting the reaction partners while stirring at temperatures in the range of from about to 180 0, preferably at to C.
• the reaction is completed after about 1 to 3 hours.
• the reaction product After having been allowed to cool and after addition of about 20 to 50% by weight, suitably 25 to 40% by weight, of a polar organic solvent such as isopropanol or propylene-glycol, the reaction product is combined with 1 to 1.1 mole of dimethylor diethyl sulfate.
• a polar organic solvent such as isopropanol or propylene-glycol
• the reaction product is combined with 1 to 1.1 mole of dimethylor diethyl sulfate.
• dialkyl sulfates quaternization may also be carried with chloro-methyl using super-atmospheric pressure.
• the concentrates of imidazolinium salts obtained in this manner constitute fluid solutions at concentrations of up to about 80% by weight.
• the imidazolinium salts of the formula -I are soluble or dispersible in water. They may be applied as softeners for textiles in known manner by impregnating the material to be treated by immersion or spraying with aqueous solutions or dispersions of these imidazolinium salts. In general, about 0.01 to 0.7%, preferably 0.05 to 0.2%, referred to the weight of the textile material, of compounds of the formula I are applied onto the textile material. In the preferred application of the softeners as additions to the last rinsing water after washing at a goods to liquor ratio of about 1:5 to 1:10 as usual for these purposes, the concentration of the imidazolinium salts amounts to about 0.02 to 1.5 g./l. of rinsing bath.
• aqueous solutions or dispersions of the softeners for textiles of the invention which in general contain about 1 to 30% by weight, in most cases 4 to by weight, of imidazolinium compounds of the formula I and about 0.3 to 30% by weight of a polar organic solvent, may also contain other components or auxiliary agents which have been admixed either to the concentrates of the imidazolinium salts or have been added separately to the aqueous solutions or dispersions or to the treatment baths destined for utilization, and which may serve, for example, for an additional influence on the handle or on other properties of the textiles to be treated or for an adjustment of the viscosity, of the regulation of the pH- value or of the increase of the stability of the solutions to cold.
• Such other components may be, for example cationic or non-ionogenic surface-active substances, electrolytes, organic complex formers, optical brighteners or solubilizers.
• the textile material After impregnation with the baths which contain the softeners for textiles of the invention, the textile material is dried in the usual manner.
• the imidazolinium salts of the invention have proved to be particularly good washing after-treatment agents. When used for this purpose, they are added, after the washing of the textile material, to the last rinsing bath.
• the imidazolinium salts of the invention confer on any textile materials, especially those of native or regenerated cellulose, wool, cellulose acetate and triacetate, polyamide, polyacrylonitrile, polyester and polypropylene, an agreeable soft handle.
• the application as washing after-treatment agent to terry towelling and underwear made of cotton is particularly advantageous.
• Example 1 93 g. of l-hydroxyethyl-Z-tallow fat-alkyl-imidazoline (content of base nitrogen 4.2%) and 5.3 g. of a 1,2-epoxyalkane having a chain length of 11 to 14 carbon atoms were heated for 2 hours to 160 C. A yellowish product was obtained (base nitrogen content 2.9%, acid number 1.5, Epon number 0), which was combined at 80 C. with 55 g. of isopropanol and quaternized at 60 C. with 31.5 g. of dimethyl sulfate. A liquid was obtained which contained 74.5% of solids and which was dispersible in cold water.
• Example 2 F 220 g. of 1-hydroxyethyl-2-fat alkyl-imidazoline (the fat alkyl rest constituted a mixture of 62% of tallow fat alkyl and 38% of behenyl alkyl) and 157 g. of a 1,2- epoxy-alkane having a chain length of 15 to 18 carbon atoms, were heated for 2 hours to 170 C. A yellowish product was obtained (content of base nitrogen 2.5%, acid number 1.2, Epon number 0) which was combined at 80 C. with 116 g. of isopropanol and which was quaternized at 60 C. with 77 g. of dimethyl sulfate. A liquid was obtained which was dispersible in cold Water and contained 75% of solids.
• Example 3 87 g. of 1-aminoethyl-2-tallow fat alkyl-imidazoline (content of base nitrogen 8.2%) were heated for 2 hours at 170 C. with 53 g. of a 1,2-epoxyalkane having a chain length of 11 to 14 carbon atoms. A yellowish product was obtained (content of base nitrogen 5.3%, acid number 1.0, Epon number 0), which was combined at C. with 60 g. of isopropanol and which was quaternized at 60 C. with 31.5 g. of dimethyl sulfate. A liquid was obtained which was dispersible in cold Water and which contained 73% of solids.
• Example 4 44.2 g. of l-aminoethyl-2-heptyl-imidazolne (content of base nitrogen 11.3%) were heated for 3 hours to C. with 53.8 g. of a 1,2-epoxyalkane having a chain length of 15 to 18 carbon atoms. A solid yellowish product was obtained (content of base nitrogen 5.2%, acid number 0.6, Epon number 0) which was combined at 80 C. with 40 g. of isopropanol and which was quaternized at 60 C. with 30.5 g. of diethyl sulfate. A liquid was obtained which was dispersible in cold water and which contained 76% of solids.
• Example 5 44.2 g. of 1-hydroxyethyl-2-heptyl-imidazoline (content of base nitrogen 7.0%) were heated for 3 hours to 100 C. with 53.8 g. of a 1,2-epoxyalkane having a chain length of 15 to 18 carbon atoms. A yellowish product was obtained (content of base nitrogen 5.3%, acid number 0, Epon number 0) which was combined at 80 C. with 35 g. of isopropanol and which was quaternized at 120 C. in an autoclave with methyl chloride. A liquid was obtained which was dispersible in cold water and which contained 73% of solids.
• Example 6 68.6 g. of 1-hydroxyethyl-Z-heptadecyl-imidazoline (content of base nitrogen 4.4%) were heated for 3 hours to 100 C. with 36.8 g. of 1,2-epoxydodecane. A yellowish product was obtained and content of base nitrogen 2.9%, acid number 0.3, Epon number 0) which was combined at 80 C. with 43 g. of isopropanol and which was quaternized at 60 C. with 25 g. of dimethyl sulfate. A liquid was obtained which was found to be dispersible in cold water and which contained 76% of solids.
• Example 7 68.8 g. of 1-aminoethyl-2-heptadecyl-imidazoline (content of base nitrogen 8.0% were heated for 3 hours to C. with 25.6 g. of 1,2-epoxyoctane. A yellowish product was obtained (content of base nitrogen 5.3%, acid number 0.9, Epon number 0) which was combined at 80 C. with 42 g. of isopropanol and then quaternized at 60 C. with 26 g. of dimethyl sulfate. A liquid was obtained which was dispersible in cold water and which contained 75% of solids.
• the concentration of the respective active substance was 0.1 g./ 1., the goods to liquor ratio was 1:10.
• the test samples were taken out from the bath, centrifuged and dried at 70 to 80 C. in a drying cabinet.
• the evaluation of the handle by the judging persons was effected after storage of the test samples for 24 hours in a climate chamber at a temperature of 20 C. and a relative air humidity of 60%.
• R represents alkyl of 9 to 12 carbon atoms and R represents the alkyl radical of the tallow fatty acid.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Applications Claiming Priority (1)

Publications (1)

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ID=5837714

Family Applications (1)

Country Status (12)

Cited By (15)

Families Citing this family (7)

• 1972
  • 1972-03-02 DE DE2210087A patent/DE2210087B2/de not_active Withdrawn
• 1973
  • 1973-02-23 NL NL7302574A patent/NL7302574A/xx not_active Application Discontinuation
  • 1973-02-27 CH CH283573A patent/CH582778A5/xx not_active IP Right Cessation
  • 1973-02-28 JP JP48023337A patent/JPS4898193A/ja active Pending
  • 1973-02-28 AT AT176573A patent/AT329169B/de not_active IP Right Cessation
  • 1973-02-28 IT IT21063/73A patent/IT979645B/it active
  • 1973-03-01 CA CA165,013A patent/CA1001634A/en not_active Expired
  • 1973-03-01 US US00337203A patent/US3849435A/en not_active Expired - Lifetime
  • 1973-03-01 BR BR731553A patent/BR7301553D0/pt unknown
  • 1973-03-02 FR FR7307497A patent/FR2174274B1/fr not_active Expired
  • 1973-03-02 GB GB1029273A patent/GB1428771A/en not_active Expired
  • 1973-03-02 BE BE128330A patent/BE796225A/xx not_active IP Right Cessation

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