US3451844A - Cationic active agent and a method for softening a washable textile fabric therewith - Google Patents

Cationic active agent and a method for softening a washable textile fabric therewith Download PDF

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Publication number
US3451844A
US3451844A US519002A US3451844DA US3451844A US 3451844 A US3451844 A US 3451844A US 519002 A US519002 A US 519002A US 3451844D A US3451844D A US 3451844DA US 3451844 A US3451844 A US 3451844A
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US
United States
Prior art keywords
softening
mole
active agent
textile fabric
cation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US519002A
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English (en)
Inventor
Helmut Kirschnek
Mathieu Quaedvlieg
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Bayer AG
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Bayer AG
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Filing date
Publication date
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Publication of US3451844A publication Critical patent/US3451844A/en
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Classifications

    • 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
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/405—Acylated polyalkylene polyamines
    • 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
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
    • 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

  • the required amounts of the cation-active compounds can readily be established during preliminary experiments; amounts of 0.1%, referred to the dry weight of the textiles to be treated, are in general already found to be suflicient.
  • the compounds to be employed according to the invention are distinguished by an unexpectedly more intensive activity compared with the fatty acid esters and fatty acid amides mentioned above, particularly with regard to an improvement in the feel of the textiles.
  • EXAMPLE 1 3 kg. of a textile fabric (towelling) consisting of cotton which had been washed and rinsed about 20 times in an automatic drum washing machine with a commercial detergent based on dodecyl-benzene sulphonate, and which had become stiff and hard after drying, are treated with the cation-active compound of the formula R is an alkyl radical of 1-4 carbon atoms; and n is an by adding 3 g. of this compound, in the form of its 7.5%
  • the cation-active compounds which can be suitably employed according to the invention may for instance be obtained by heating 1 mole of the compound of the formula with 1 mole of the compound of the formula R -COOH and 1 mole of the formula R COOH at 180 to 190 C. for several hours; in these formulae the symbols R R R and R, as well as X and n have the significance mentioned above.
  • the cation-active compounds are conveniently employed in the form of their salts with lower organic acids or with inorganic acids, such as formic acid and acetic acid or hydrochloric acid and phosphoric acid.
  • inorganic acids such as formic acid and acetic acid or hydrochloric acid and phosphoric acid.
  • aqueous emulsion which also contains 3.8% acetic acid as well as 1% oleyl alcohol polyglycol ether, to the last rinsing liquor during a further washing operation.
  • the fabric which has thus been treated then no longer exhibits hardness or stiffness after drying, but has a pleasant soft feel.
  • EXAMPLE 2 (1 mole) were reacted with a mixture of 256 g. (1 mole) palmitic acid and 284 g. stearic acid (1 mole) as well as with 10.2 g. acetic anhydride (0.1 mole) by the method described in Example 1. Thereafter, 75 g. of the resultant cation-active compound of the formula 4 with 10.2 g. acetic anhydride (0.1 mole) by the method described in Example 1. 75 g. of the cation-active com- CHzCHa EXAMPLE 3 3 kg.
  • EXAMPLE 4 3 kg. of a mixed fabric consisting of polyester fibres and rayon which had been washed and rinsed 20 times in an automatic washing machine with a commercial detergent based on dodecyl-benzene sulphonate and which had become stiff and hard after drying, are treated with the cation-active compound of the formula pound thus obtained were then stirred with 905 g. water, with 10 g. of the reaction product of 25 moles ethylene oxide with 1 mole oleyl alcohol and with 10 g. 100% formic acid by the method described in Example 1 to form an aqueous emulsion.
  • R and R are individually defined as alkyl radicals of 11-21 carbon atoms; R is hydrogen or methyl; R is an alkyl radical of 14 carbon atoms; and n is an integer of 0-2.
  • R and R are respectively alkyl of 15-17 carbon atoms; R is hydrogen; R is ethyl and n is 1.
  • a method for softening washable textiles comprising contacting the textiles with an active amount of a compound of claim 1.
  • Washable textiles are cotton, polyacrylonitrile, lWOOl, polyester or rayon, and about 1% by weight of active compound is utilized by weight of dry textile.

Landscapes

  • 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)
US519002A 1965-01-20 1966-01-06 Cationic active agent and a method for softening a washable textile fabric therewith Expired - Lifetime US3451844A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF0045004 1965-01-20

Publications (1)

Publication Number Publication Date
US3451844A true US3451844A (en) 1969-06-24

Family

ID=7100301

Family Applications (1)

Application Number Title Priority Date Filing Date
US519002A Expired - Lifetime US3451844A (en) 1965-01-20 1966-01-06 Cationic active agent and a method for softening a washable textile fabric therewith

Country Status (7)

Country Link
US (1) US3451844A (enEXAMPLES)
BE (1) BE675375A (enEXAMPLES)
CH (1) CH419042A (enEXAMPLES)
DE (1) DE1469359A1 (enEXAMPLES)
FR (1) FR1465039A (enEXAMPLES)
GB (1) GB1111396A (enEXAMPLES)
NL (1) NL6600468A (enEXAMPLES)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2156772A1 (enEXAMPLES) * 1971-10-18 1973-06-01 Procter & Gamble
US3844959A (en) * 1972-10-16 1974-10-29 Procter & Gamble Detergent composition with an amido-amine fabric softening agent
US4044034A (en) * 1975-07-22 1977-08-23 The Miranol Chemical Company, Inc. Nitrogenous condensation products

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7609628A (nl) * 1975-09-04 1977-03-08 Hoechst Ag Textielbehandelingsmiddel.
DE2539349C2 (de) * 1975-09-04 1985-04-11 Hoechst Ag, 6230 Frankfurt Wäschenachbehandlungsmittel
US4762645A (en) * 1987-11-16 1988-08-09 The Procter & Gamble Company Detergent plus softener with amide ingredient
NZ235490A (en) * 1989-10-16 1993-08-26 Colgate Palmolive Co Fabric-softening compositions

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2205042A (en) * 1937-10-26 1940-06-18 Du Pont Softening of textile materials and compositions therefor
US2243980A (en) * 1936-10-30 1941-06-03 Sandoz Ltd Softening textiles
US2496776A (en) * 1946-06-21 1950-02-07 Eastman Kodak Co Textile yarns impregnated with lubricating compositions
US2734830A (en) * 1950-01-13 1956-02-14
US3038820A (en) * 1955-07-15 1962-06-12 Ciba Ltd Process for imparting a soft feel to textile fibers
US3095373A (en) * 1959-01-30 1963-06-25 Wyandotte Chemicals Corp Fabric softeners
US3168416A (en) * 1957-04-23 1965-02-02 Atlas Chem Ind Textile yarn coated with cationic surfactant

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2243980A (en) * 1936-10-30 1941-06-03 Sandoz Ltd Softening textiles
US2205042A (en) * 1937-10-26 1940-06-18 Du Pont Softening of textile materials and compositions therefor
US2496776A (en) * 1946-06-21 1950-02-07 Eastman Kodak Co Textile yarns impregnated with lubricating compositions
US2734830A (en) * 1950-01-13 1956-02-14
US3038820A (en) * 1955-07-15 1962-06-12 Ciba Ltd Process for imparting a soft feel to textile fibers
US3168416A (en) * 1957-04-23 1965-02-02 Atlas Chem Ind Textile yarn coated with cationic surfactant
US3095373A (en) * 1959-01-30 1963-06-25 Wyandotte Chemicals Corp Fabric softeners

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2156772A1 (enEXAMPLES) * 1971-10-18 1973-06-01 Procter & Gamble
US3844959A (en) * 1972-10-16 1974-10-29 Procter & Gamble Detergent composition with an amido-amine fabric softening agent
US4044034A (en) * 1975-07-22 1977-08-23 The Miranol Chemical Company, Inc. Nitrogenous condensation products

Also Published As

Publication number Publication date
BE675375A (enEXAMPLES) 1966-05-16
GB1111396A (en) 1968-04-24
FR1465039A (fr) 1967-01-06
DE1469359A1 (de) 1968-12-19
NL6600468A (enEXAMPLES) 1966-07-21
CH419042A (de) 1966-08-31

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