EP0038862B1 - Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles - Google Patents

Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles Download PDF

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Publication number
EP0038862B1
EP0038862B1 EP19790301558 EP79301558A EP0038862B1 EP 0038862 B1 EP0038862 B1 EP 0038862B1 EP 19790301558 EP19790301558 EP 19790301558 EP 79301558 A EP79301558 A EP 79301558A EP 0038862 B1 EP0038862 B1 EP 0038862B1
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Prior art keywords
composition according
amido amine
water
groups
foregoing
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EP19790301558
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German (de)
English (en)
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EP0038862A1 (fr
Inventor
Daniele Fontanesi
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Solvay Solutions UK Ltd
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Albright and Wilson Ltd
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Priority to EP19790301558 priority Critical patent/EP0038862B1/fr
Priority to DE7979301558T priority patent/DE2966608D1/de
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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
    • C11D1/52—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
    • C11D3/0015—Softening compositions liquid
    • 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

Definitions

  • This invention relates to fabric softener compositions containing amido amino salts, and the use thereof for the treatment of fabrics.
  • the five most commonly found active softening agents in consumer products purchased in the U.S.A. are all quaternary nitrogen compounds: (1) a methyl chloride quaternised tertiary amine, (II) a dimethyl sulphate quaternised tertiary amine, (III) a dimethyl sulfphate quaternised polyethoxylated di amido amine, (IV) a dimethyl sulphate quaternised polypropoxylated diamido amine and (V) a dimethyl sulphate quaternised alkyl amido alkyl imidazoline.
  • German Patent Application No. 2520150 (Brit. Pat. 1,483,984) for example describes the preparation of a quaternised mixture of a diamido diethylenetriamine and an imidazoline.
  • the presence of the quaternised diamido diethylenetriamine is said to lower the softening effect of the mixture compared with the quaternised imidazoline alone but to improve the rewettability of the fabric after washing, which most known fabric softeners reduce.
  • the patent implies that quaternised diamido diethylenetriamines alone are not effective fabric softeners.
  • unquaternised diamido amines, their salts and partial salts tend to be intractable solids at room temperature, which even on dilution with a suitable solvent e.g. 25% of a lower alkanol such as isopropanol, hexylene glycol, propylene glycol or mixtures thereof, are still to viscous for convenient handling.
  • a suitable solvent e.g. 25% of a lower alkanol such as isopropanol, hexylene glycol, propylene glycol or mixtures thereof, are still to viscous for convenient handling.
  • Our invention therefore provides a novel composition which comprises (A) a water dispersible salt or partial salt of an amido amine of the average formula: wherein an average of from 20% to 80% of the R groups per molecule are acyl groups having an average of from 12 to 22 and preferably 16 to 18 carbon atoms, at least 20% of the R groups are -CH 2 CH 2 0H or -CH Z CH(OH)CH 3 or mixtures of these groups and any other R group is hydrogen, n is 2 or 3 and m is an integer from 2 to 5; which amido amine is at least partially (e.g. from 10% to 80%, preferably 20 to 60%) neutralised with a lower carboxylic or hydroxycarboxylic acid, e.g.
  • acetic, formic, propionic, lactic or glycollic acid and (B) a compatible amount, up to 70% preferably 10 to 50%, e.g. 25% by weight, of a fluid, water miscible hydroxyaliphatic solvent.
  • R groups are acyl they can be saturated, e.g. stearoyl, monounsaturated, e.g. oleoyl, polyunsaturated or may be mixtures of these types.
  • the preferred compounds are those wherein n and m are each 2.
  • the acyl groups are derived from tallow or lard.
  • any water miscible hydroxy-, or polyhydroxy- alkane or alkylether having a viscosity of less than 0.03 N.S.M.- 2 (30 centipoise) at 20°C may be used as the solvent.
  • Preferred examples include isopropanol, hexylene glycol, propylene glycol, ethylene glycol monomethylether and mixtures thereof.
  • the product may additionally contain a minor proportion of salts of inorganic acids especially sulphites, which help to stabilise the product against oxidation.
  • the amido amines may be obtained by controlled alkoxylation of an amido amine prepared by amidating a polyalkylene polyamine, e.g. by heating it with the necessary amount of a glyceryl ester to provide the desired alkyl groups in the correct proportions.
  • the polyamine may be heated with a fatty acid or methyl ester thereof while distilling off water or methanol respectively.
  • the heating is carried out at temperatures above 100°C but not sufficiently high to decompose any glycerol formed.
  • the temperature should be maintained below 180°C and preferably at 120 to 160°C, e.g. 140°C.
  • Heating is preferably carried in an inert atmosphere to prevent colour degradations, e.g. under nitrogen for from 2 to 6, preferably 4 hours.
  • the product may then be reacted with ethylene or propylene oxide at a temperature between 100 and 200°C.
  • the presence of a catalyst should generally be avoided in order to prevent formation of polyoxyalkylene chains.
  • the solvent may be added after alkoxylation to facilitate dispersion of the product in water.
  • the invention provides softening compositions comprising the amido amine salts, any glycerol remaining from the preparation of the diamide and the added solvent.
  • the novel products of our invention may be used in conventional manner, e.g. as a post-rinse after washing.
  • substantially monoethoxylated products of our invention are significantly more fluid in the presence of organic solvent than corresponding non-ethoxylated diamidoamines.
  • the vessel was evacuated and flushed with nitrogen to displace most of the air.
  • the reactor charge was then cooled to 120°C and 132 kg of ethylene oxide fed in slowly cooling to maintain 120°C.
  • the product is a hazy, mobile, pumpable liquid at 20°C.
  • the above preparation was repeated but without the addition of solvents.
  • the product was a waxy solid which was fluid at 40 to 45°C. On dilution to 75% with isopropanol the product became pourable at 20°C.
  • Domestic fabric softener formulations normally consist of concentrated fabric softener solutions as prepared in examples 1 and 2 dispersed into water to yield translucent liquids containing normally 2% to 8% "active" softener.
  • active we mean the non solvent component in a fabric softener concentrate.
  • Example 3 the appearance and stability of the aqueous dispersion of the concentrates is important for consumer acceptability. Products which yield stable dispersions with viscosities in the range 0.1 to 0.5 N.S.M.- 2 (100 to 500 centipoise) as measured by a "Brookfield" viscometer, model LVT, find ready consumer acceptability. Products which give dispersions which change viscosity on storage are obviously undesirable.
  • types II, III, IV and V give dispersions at 6% "active" with viscosities in the range 0.01 to 0.03 N.S.M.- 2 (10 to 30 cp) and are often formulated with other additives to increase their viscosity.
  • Dispersions prepared from products of examples 1 and 2 are stable to extend storage.
  • the weight of active material used was in the range 0.1 to 0.3% of the napkin weight.
  • the napkins were then wrung out by hand and dried on a clothes line under the same conditions.
  • Example 2 shows better rewettability properties than type I which has a similar softening ability.

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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)

Claims (8)

1. Composition fluide, dispersable dans l'eau pour utilisation comme adoucissant pour matières textiles, caractérisée en ce qu'elle comprend:
(A) un sel ou un sel partiel, dispersable dans l'eau, d'une amido-amine de formule moyenne:
Figure imgb0013
dans laquelle une moyenne de 20 à 80% des groupes R par molécule sont des groupes acyles ayant en moyenne de 12 à 22 atomes de carbone, au moins 20% des groupes R sont ―CH2CH2OH ou -CHZCHOHCH3 ou des mélanges de ces groupes et tout autre groupe R est l'hydrogène, n est 2 ou 3 et m est un nombre entier compris entre 2 et 5; cette amido-amine ayant été au moins partiellement neutralisée avec un acide carboxylique ou hydroxy-carboxylique ayant de 1 à 3 atomes de carbone, et
(B) jusqu'à 70% en poids d'un solvant hydroxylé aliphatique, fluide, miscible à l'eau.
2. Composition selon la revendication 1, caractérisée en ce que le groupe acyle dérive du suif ou du lard.
3. Composition selon l'une des revendications 1 et 2, caractérisée en ce que l'amido-amine est neutralisée entre 10% et 80% avec l'acide lactique ou l'acide acétique.
4. Composition selon l'une quelconque des revendications précédentes, contenant de 10 à 50% en poids de la composition, en solvant hydroxylé aliphatique.
5. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce que le solvant hydroxylé aliphatique est un hydroxy- ou polyhydroxyalcane ou éther alkylique.
6. Composition selon la revendication 5, caractérisée en ce que le solvant hydroxylé aliphatique a moins de 4 atomes de carbone.
7. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce que n et m sont chacun 2.
8. Procédé d'adoucissement des matières textiles, caractérisé en ce qu'il consiste à mettre sur les matières textiles une solution ou une dispersion aqueuse d'une composition selon l'une quelconque des revendications précédentes.
EP19790301558 1979-08-03 1979-08-03 Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles Expired EP0038862B1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP19790301558 EP0038862B1 (fr) 1979-08-03 1979-08-03 Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles
DE7979301558T DE2966608D1 (en) 1979-08-03 1979-08-03 Compositions containing amido amine salts, and their use as fabric softeners

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP19790301558 EP0038862B1 (fr) 1979-08-03 1979-08-03 Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles

Publications (2)

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EP0038862A1 EP0038862A1 (fr) 1981-11-04
EP0038862B1 true EP0038862B1 (fr) 1984-02-01

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Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8508129D0 (en) * 1985-03-28 1985-05-01 Procter & Gamble Ltd Textile treatment composition
DE3601856A1 (de) * 1986-01-23 1987-07-30 Henkel Kgaa Textilbehandlungsmittel
FR2613386B1 (fr) * 1987-04-04 1993-06-18 Sandoz Sa Nouvelles compositions pour le finissage des matieres fibreuses
US4762645A (en) * 1987-11-16 1988-08-09 The Procter & Gamble Company Detergent plus softener with amide ingredient
DE3842057A1 (de) * 1988-12-14 1990-06-28 Henkel Kgaa Textile weichmacher fuer flotten mit hohen gehalten an elektrolyten und/oder optischen aufhellern
DE3901820A1 (de) * 1989-01-23 1990-08-09 Henkel Kgaa Textilbehandlungsmittel
DE4111648A1 (de) * 1991-04-10 1992-10-15 Henkel Kgaa Textilbehandlungsmittel mit verbesserter wasserdispergierbarkeit
MY108928A (en) * 1992-12-22 1996-11-30 Colgate Palmolive Co Liquid fabric softening composition containing amidoamine softening compound
US5433869A (en) * 1992-12-22 1995-07-18 Colgate-Palmolive Co. Liquid fabric conditioning composition containing amidoamine softening compound
GB9301811D0 (en) * 1993-01-29 1993-03-17 Unilever Plc Fabric softener composition
DE19625937A1 (de) 1996-06-28 1997-01-23 Huels Chemische Werke Ag Verfahren zur Herstellung von Mono-, Di- oder Oligoamidalkoxylaten
US5747109A (en) * 1997-03-19 1998-05-05 Colgate-Palmolive Co. Method of preparing super-concentrated liquid rinse cycle fabric softening composition
US5747108A (en) * 1997-03-19 1998-05-05 Colgate-Palmolive Co. Super-concentrated liquid rinse cycle fabric softening composition
DE19756680A1 (de) * 1997-12-19 1999-06-24 Henkel Kgaa Fettsäureamidoamide
US6780834B2 (en) 2002-07-31 2004-08-24 Colgate-Palmolive Co. Fabric conditioning compositions containing an amine acid softening compound
DK1902083T3 (da) 2005-06-29 2011-01-10 Colgate Palmolive Co Oligomere amidoaminer eller amidoquats til behandlingssammensætninger for tøj eller hår
CN101730676A (zh) 2007-06-28 2010-06-09 尼科克斯公司 1,4-丁二醇单硝酸酯的制备方法
CA3043877A1 (fr) 2016-12-01 2018-06-07 Croda, Inc. Compositions de soins personnels comprenant une amidoamine dialkyle

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3844959A (en) * 1972-10-16 1974-10-29 Procter & Gamble Detergent composition with an amido-amine fabric softening agent
US3933871A (en) * 1973-11-12 1976-01-20 Armstrong Chemical Company, Inc. Fabric softener compound and processes for preparing and using the same
FR2273901A1 (fr) * 1974-06-06 1976-01-02 Azote & Prod Chim Composition pour le traitement de textiles
US4039565A (en) * 1975-06-26 1977-08-02 Ashland Oil, Inc. Quaternized amidoamines
DE2539310A1 (de) * 1975-09-04 1977-03-17 Hoechst Ag Textilweichmacher

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EP0038862A1 (fr) 1981-11-04
DE2966608D1 (en) 1984-03-08

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