EP0454741B1 - Agents de traitement de textiles - Google Patents

Agents de traitement de textiles Download PDF

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Publication number
EP0454741B1
EP0454741B1 EP90902188A EP90902188A EP0454741B1 EP 0454741 B1 EP0454741 B1 EP 0454741B1 EP 90902188 A EP90902188 A EP 90902188A EP 90902188 A EP90902188 A EP 90902188A EP 0454741 B1 EP0454741 B1 EP 0454741B1
Authority
EP
European Patent Office
Prior art keywords
textile treatment
mol
amino groups
acid
unreacted amino
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
EP90902188A
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German (de)
English (en)
Other versions
EP0454741A1 (fr
Inventor
Günter Uphues
Uwe Ploog
Klaudia Bischof
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to AT90902188T priority Critical patent/ATE90120T1/de
Publication of EP0454741A1 publication Critical patent/EP0454741A1/fr
Application granted granted Critical
Publication of EP0454741B1 publication Critical patent/EP0454741B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • D06M13/10—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 oxygen
    • D06M13/144—Alcohols; Metal alcoholates
    • D06M13/148—Polyalcohols, e.g. glycerol or glucose
    • 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

  • the invention relates to textile treatment agents based on condensation products of carboxylic acids or carboxylic acid derivatives with polyamines, which are particularly well dispersible in water.
  • the invention further relates to a method for producing the textile treatment agents and their use.
  • textile treatment agents are understood to mean products which can be used in agents for finishing fibers and yarns, in detergents and in post-treatment agents for washed textiles.
  • DE-A-19 22 046 describes detergents containing fatty acid condensation products which contain fatty acid partial glycerides which have a dispersing action
  • DE-A-19 22 047 describes these fatty acid condensation products as textile softeners for, in particular, liquid laundry aftertreatment agents.
  • These and similar textile treatment agents can be dispersed in water by heating the water and usually using high shear forces, or by dispersing the condensation product, which has still been melted, in water. Because of the effort required, the manufacturer usually carries out the dispersion and delivers the dispersions to the user, which is associated with the transport of considerable amounts of water.
  • such active substances are added to hydrophilic dispersion accelerators to improve the dispersibility.
  • the effect of the dispersion accelerator is particularly good if, according to the teaching of DE-A-37 30 792.4, these substances are already present in the reaction mixture during the condensation reaction.
  • DE-A-36 01 856 reaction products of aliphatic monocarboxylic acids and polyamines are known whose unreacted amino groups are neutralized with an up to 30 percent excess or deficit of non-oxidizing inorganic acids to reduce the tendency to discolouration when exposed to heat.
  • textile treatment agents based on fatty acid condensation products with improved dispersibility, especially in cold water, so that the user himself can easily disperse the textile treatment agents.
  • a textile treatment agent which can be prepared by reacting a) aliphatic monocarboxylic acids with 8 to 22 carbon atoms or derivatives forming amides with b) optionally hydroxyl-substituted polyamines and subsequent neutralization of unreacted amino groups, the textile treatment agent an addition of dispersion accelerators selected from the group of monosaccharides of the aldose and ketose type and the polyhydroxy compounds derived therefrom by hydrogenation, the polyols, such as in particular pentaerythritol, dipentaerythritol, trimethylolpropane, the alkylglycosides, the sorbitan esters, to which ethylene oxide is attached, if desired, and contains the natural and synthetic hydrophilic polymers, characterized in that the unreacted amino groups are neutralized to 30 to 60 mol%. In contrast to the complete neutralization with stoichiometric or excess amounts of acids, this partial neutralization with inferior amounts of acid surprisingly brings about improved
  • Amide-forming derivatives of aliphatic monocarboxylic acids are understood to mean the esters derived from natural or synthetic fatty acids or fatty acid mixtures with lower alkanols such as, for example, methanol or ethanol, the fatty acid glycerides and the fatty acid halides.
  • these are the derivatives derived from lauric acid, myristic acid, palmitic acid, stearic acid, coconut fatty acid, tallow fatty acid or rapeseed oil fatty acid.
  • the reaction products which can be produced from this by reaction with polyamines are hereinafter called fatty acid condensation products, which also include imidazolines in the case of the reaction of diethylenetriamine with 2 mol of fatty acid or fatty acid derivatives.
  • Suitable polyamines are preferably derived from optionally hydroxyl-substituted ethylenediamine or diethylenetriamine, such as. B. of dihydroxyethylene diamine, hydroxyethyl diethylene triamine, Hydroxypropyldiethylenetriamine, and especially hydroxyethylethylenediamine. N, N-dimethyl-1,3-diaminopropane, triethylene tetramine or tetraethylene pentamine are also suitable.
  • Lower carboxylic acids in particular low molecular weight organic mono- or polycarboxylic acids which are optionally substituted by hydroxyl groups, such as, for example, glycolic acid, citric acid, lactic acid or acetic acid, are suitable for neutralizing unreacted amino groups.
  • monobasic inorganic acids such as. B. hydrochloric acid or sulfonic acids such as methanesulfonic acid or p-toluenesulfonic acid.
  • Particularly suitable as textile softeners are the widely used dimethyl di (C8 to C22-alkyl / alkenyl) ammonium salts such as dimethyl-ditalgalkyl-ammonium chloride or dimethyl-distearyl-ammonium chloride or methosulfate. It is then generally advantageous that the reaction products are already in a mixture with the other textile treatment active ingredients in the partial neutralization of unreacted amino groups.
  • the monosaccharides of the aldose and ketose type or their hydrogenation products which can be used as dispersion accelerators have 4, 5 or in particular 6 carbon atoms in the molecule.
  • Examples are fructose, sorbose and in particular glucose, sorbitol and mannitol, which are inexpensive and effective.
  • Polyols such as, in particular, pentaerythritol, dipentaerythritol and trimethylolpropane are very suitable.
  • Suitable alkyl glycosides are obtained by the Fischer process by reacting monosaccharide with fatty alcohol in the presence of an acidic catalyst.
  • Alkyl glycosides, the alkyl group of which contains up to 16 carbon atoms, have long been known as surfactants.
  • Suitable sorbitan esters are esters with saturated or unsaturated fatty acids having 10 to 20 carbon atoms, in particular sorbitan oleate. 2 to 20 moles of ethylene oxide can additionally be added to the sorbitan esters.
  • Natural or synthetic hydrophilic polymers are also suitable as dispersion accelerators.
  • a preferred natural polymer in this class is gelatin. Mixtures of gelatin and monosaccharides or their hydrogenation products are particularly suitable.
  • Other useful natural hydrophilic polymers are e.g. B. guar, dextrin, gum arabic, agar agar, casein.
  • homopolymers or copolymers based on polyvinyl alcohol, polyacrylic acid and polyvinylpyrrolidone should be mentioned in particular.
  • the suitable polymers have in common that they are easily soluble or dispersible or swellable in water.
  • dispersion accelerators required to achieve rapid dispersibility in a short time are in particular in the range from 0.5 to 10% by weight, based on the amount of dispersion accelerator and fatty acid condensation product.
  • Textile treatment compositions which, as dispersion accelerators, monosaccharides and / or their hydrogenation products, in particular glucose, sorbitol, mannitol or mixtures thereof, preferably in Amounts of 2.5 to 10% by weight, just like textile treatment agents which contain 5 to 10% by weight of gelatin, have particularly good properties.
  • agents which contain mixtures of monosaccharides and / or their hydrogenation products with gelatin as dispersion accelerators have particularly good properties.
  • Agents which contain 1 to 5% by weight of pentaerythritol as dispersion accelerators also have particularly good properties.
  • the presence of further dispersants for example fatty alcohol alkoxylates or oxo alcohol alkoxylates with 10 to 20 carbon atoms in the alcohol component and with 2 to 50 moles of alkylene oxide, in particular ethylene oxide and / or propylene oxide, preferably tallow alcohol + 50 moles of ethylene oxide or coconut alcohol + 5 moles of ethylene oxide + 4 Moles of propylene oxide, partial fatty acid glycerides and / or water-miscible solvents such as propylene glycol or glycerin are useful.
  • the amount of additional dispersants in the textile treatment agents according to the invention can make up 0.5 to 70% by weight of the textile treatment agent.
  • the present invention further relates to a method for producing the textile treatment agents mentioned.
  • the process according to the invention is characterized in that the unreacted amino groups are neutralized to 30 to 60 mol%.
  • the fatty acid condensation products known per se for example, the fatty acid or the fatty acid derivative and the polyamine are used in a molar ratio of 1: 1 to 3: 1 (carboxylic acid to polyamine).
  • the reaction components are heated, if appropriate in the presence of the dispersion accelerator, with constant mixing until virtually all the fatty acid or the fatty acid derivative is implemented.
  • unreacted amino groups are neutralized with low molecular weight organic carboxylic acids or hydroxycarboxylic acids or monobasic inorganic acids, for example by mixing the melt of the fatty acid condensation product with the calculated amount of acid, or the amine salt is formed by dissolving or dispersing the reaction product in the organic acid or one Organic acid solution.
  • the acid used for salt formation is added in such an amount as is required for 30 to 60 mol% neutralization. If the dispersion accelerator has not already been added during the condensation reaction, the addition takes place after the neutralization. Working in an intergas atmosphere and / or the addition of a reducing agent in the condensation reaction leads to particularly light-colored products. Hypophosphorous acid has proven particularly useful as a reducing agent.
  • the textile treatment agents according to the invention are obtained, for example, as powders, flakes or pellets and can easily be processed into stable dispersions in water, in particular also in cold water. All you need to do is mix with water and then stir gently. The dispersions obtained are extremely stable and do not tend to separate.
  • the dispersions of textile treatment agents are used in a variety of ways to treat fibers, yarns or fabrics. The treatment of fibers or yarns is carried out using methods that are customary in textile technology, such as pull-out, immersion centrifugal, foulard or spray processes.
  • textile treatment agents can also be used as components of aftertreatment agents for washed textiles, as a result of which the textiles become soft and antistatic.
  • the aftertreatment of the washed textiles can usually be carried out in the last rinsing bath, but also during drying in an automatic laundry dryer, either by spraying the laundry with a dispersion of the agent during drying or by applying the agent to a substrate, for example a flexible textile fabric, applies.
  • the products according to the invention can have different compositions, ie the fatty acid condensation products can contain a more or less large fatty acid component, or a fatty acid component with fatty acid residues of different lengths.
  • the fatty acid condensation products can contain a more or less large fatty acid component, or a fatty acid component with fatty acid residues of different lengths.
  • those products according to the invention which have a proportion of 0.5 to 1 fatty acid residue, which is preferably saturated, with essentially 16 to 22 carbon atoms on a functional group of the Have polyamines, that is, amino or hydroxyl group.
  • the aftertreatment agents according to the invention are also excellently suitable for the production of aqueous fabric softener concentrates which have an active ingredient concentration of 10 to 50% by weight instead of the usual active ingredient concentration of about 5% by weight.
  • those products are preferably selected which have condensation products of shorter fatty acid esters, ie with essentially 12 to 16 carbon atoms and a proportion of 0.3 to 1, preferably 0.3 to 0.5, fatty acid residues per functional group of the hydroxyalkyl polyamine .
  • a fatty acid condensation product known per se which was suitable for textile finishing was prepared by adding 1215 g (4.5 mol) of technical stearic acid and 312 g (3 mol) of aminoethylethanolamine in a three-necked flask, equipped with a stirrer, thermometer, gas inlet tube and distillation head within 2.5 hours Heated to 200 ° C. under a nitrogen blanket and thereby splitting off water. The reaction was continued until the acid number, determined by DGF method C-V 2, had dropped to a value of 2.0. The content of amine nitrogen still present, determined by titration with perchloric acid in acetic acid medium, was 1.65%. After cooling to 90 ° C., the melt was transferred on a flake roller into light yellow, non-adhesive flakes with a melting range of 64-67 ° C.
  • a product according to Example 1 was produced and further treated as follows:
  • Example 2 As described in Example 1, 351 g (1.3 mol) of technical stearic acid and 104 g (1 mol) of aminoethylethanolamine were reacted. After an acid number of 2.5 was reached, the reaction was terminated. The content of amine nitrogen still present was 2.31%. 250 g (0.413 equivalents of amine nitrogen) of the condensation product were mixed at 90-100 ° C. with 16.2 g (0.144 mol) of lactic acid, 80% and then with 11.1 g of sorbitol. The clear melt was converted into the scale form.
  • Example 2 As described in Example 1, 459 g (1.7 mol) of technical stearic acid and 104 g (1 mol) of aminoethylethanolamine were reacted. After an acid number of 4 had been reached, the reaction was terminated. The content of amine nitrogen still present was 1.17%. 250 g (0.209 equivalents of amine nitrogen) of the condensation product were mixed with 11.8 g (0.105 mol) of lactic acid at 90-100 ° C. 80% and then mixed with 10.9 sorbitol. The clear melt was converted into the scale form.
  • Example 7 was repeated. Finally, about 24% (0.22 mol) of lactic acid, 80%, was neutralized to about 100 mol%.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Polyamides (AREA)
  • Detergent Compositions (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)

Claims (6)

  1. Agent pour le traitement des textiles, obtenable par mise en réaction a) d'acides monocarboxyliques aliphatiques comportant 8 à 22 atomes de carbone ou de leurs dérivés formant des amides avec b) des polyamines le cas échéant à substitution hydroxyle, suivie de neutralisation des groupes amino non entrés en réaction, l'agent pour le traitement des textiles étant additionné d'accélérateurs de dispersion, sélectionnés parmi le groupe des monosaccharides du type des aldoses et des cétoses et des composés polyhydroxyliques dérivés de celles-ci par hydrogénation, des polyols, tels en particulier la pentaérythrite, la dipentaérythrite, le tryméthylolpropane, des alkylglucosides et des esters de sorbitane, auxquels de l'oxyde d'éthylène est éventuellement fixé par addition, et des polymères hydrophiles naturels et synthétiques, caractérisé en ce que les groupes amino non entrés en réaction sont neutralisés à raison de 30 à 60 moles %.
  2. Agent pour le traitement des textiles selon la revendication 1, caractérisé en ce que les produits de réaction sont présents lors de la neutralisation partielle des groupes amino non entrés en réaction, en mélange avec les autres substances actives pour le traitement des textiles, en particulier les assouplissants pour les textiles du type du sel de diméthyl-di-(alkyl /alcényl en C₈ à C₂₂)-ammonium.
  3. Procédé de fabrication d'un agent pour le traitement des textiles selon l'une des revendications 1 ou 2, par mise en réaction a) d'acides monocarboxyliques aliphatiques comportant 8 à 22 atomes de carbone ou de leurs dérivés formant des amides avec b) des polyamines le cas échéant à substitution hydroxyle, suivie de neutralisation des groupes amino non entrés en réaction, l'agent pour le traitement des textiles étant additionné d'accélérateurs de dispersion, sélectionnés parmi le groupe des monosaccharides du type des aldoses et des cétoses et des composés polyhydroxyliques dérivés de celles-ci par hydrogénation, des polyols, tels en particulier la pentaérythrite ou le tryméthylolpropane, des alkylglucosides et des esters de sorbitane, auxquels de l'oxyde d'éthylène est éventuellement fixe par addition, et des polymères hydrophiles naturels et synthétiques, caractérisé en ce que l'on neutralise les groupes amino non entrés en réaction à raison de 30 à 60 moles %.
  4. Utilisation des agents pour le traitement des textiles selon l'une des revendications 1 ou 2 pour l'ennoblissement des fibres, fils ou tissus.
  5. Utilisation des agents pour le traitement des textiles selon l'une des revendications 1 ou 2 pour le lavage des textiles.
  6. Utilisation des agents pour le traitement des textiles selon l'une des revendications 1 ou 2 pour le posttraitement du linge lavé.
EP90902188A 1989-01-23 1990-01-15 Agents de traitement de textiles Expired - Lifetime EP0454741B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT90902188T ATE90120T1 (de) 1989-01-23 1990-01-15 Textilbehandlungsmittel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3901820 1989-01-23
DE3901820A DE3901820A1 (de) 1989-01-23 1989-01-23 Textilbehandlungsmittel

Publications (2)

Publication Number Publication Date
EP0454741A1 EP0454741A1 (fr) 1991-11-06
EP0454741B1 true EP0454741B1 (fr) 1993-06-02

Family

ID=6372576

Family Applications (2)

Application Number Title Priority Date Filing Date
EP90902188A Expired - Lifetime EP0454741B1 (fr) 1989-01-23 1990-01-15 Agents de traitement de textiles
EP90100742A Withdrawn EP0379923A1 (fr) 1989-01-23 1990-01-15 Agent de traitement de textile

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP90100742A Withdrawn EP0379923A1 (fr) 1989-01-23 1990-01-15 Agent de traitement de textile

Country Status (13)

Country Link
US (1) US5238586A (fr)
EP (2) EP0454741B1 (fr)
JP (1) JPH04503088A (fr)
KR (1) KR970011243B1 (fr)
AT (1) ATE90120T1 (fr)
AU (1) AU4951590A (fr)
BR (1) BR9007045A (fr)
CA (1) CA2008361A1 (fr)
DE (2) DE3901820A1 (fr)
ES (1) ES2044555T3 (fr)
TR (1) TR25133A (fr)
WO (1) WO1990008217A1 (fr)
ZA (1) ZA90445B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4111648A1 (de) * 1991-04-10 1992-10-15 Henkel Kgaa Textilbehandlungsmittel mit verbesserter wasserdispergierbarkeit
KR940011469B1 (ko) * 1992-10-19 1994-12-15 주식회사선경인더스트리 폴리에스테르계 직편물의 코팅가공방법
DE4312008A1 (de) * 1993-04-13 1994-10-20 Henkel Kgaa Fettsäureamide
US6204208B1 (en) 1996-09-04 2001-03-20 Kimberly-Clark Worldwide, Inc. Method and composition for treating substrates for wettability and skin wellness
US6028016A (en) * 1996-09-04 2000-02-22 Kimberly-Clark Worldwide, Inc. Nonwoven Fabric Substrates Having a Durable Treatment
US6060636A (en) * 1996-09-04 2000-05-09 Kimberly-Clark Worldwide, Inc. Treatment of materials to improve handling of viscoelastic fluids
US6296936B1 (en) 1996-09-04 2001-10-02 Kimberly-Clark Worldwide, Inc. Coform material having improved fluid handling and method for producing
US6017832A (en) * 1996-09-04 2000-01-25 Kimberly-Clark Worldwide, Inc. Method and composition for treating substrates for wettability

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3454494A (en) * 1965-08-03 1969-07-08 Standard Chem Products Inc Textile softener compositions
US3965015A (en) * 1972-08-01 1976-06-22 Colgate-Palmolive Company Bleach-resistant fabric softener
DE2621881C2 (de) * 1976-05-17 1985-10-31 Henkel KGaA, 4000 Düsseldorf Glättemittel für Textilfasermaterial
GB1599171A (en) * 1977-05-30 1981-09-30 Procter & Gamble Textile treatment composition
DE2966608D1 (en) * 1979-08-03 1984-03-08 Albright & Wilson Compositions containing amido amine salts, and their use as fabric softeners
DE3530302A1 (de) * 1985-08-24 1987-03-05 Henkel Kgaa Textilbehandlungsmittel
DE3601856A1 (de) * 1986-01-23 1987-07-30 Henkel Kgaa Textilbehandlungsmittel
EP0300098B1 (fr) * 1987-07-21 1991-11-21 Agfa-Gevaert N.V. Méthode d'enduction
DE3730792A1 (de) * 1987-09-14 1989-03-23 Henkel Kgaa Textilbehandlungsmittel

Also Published As

Publication number Publication date
JPH04503088A (ja) 1992-06-04
DE3901820A1 (de) 1990-08-09
KR970011243B1 (ko) 1997-07-08
TR25133A (tr) 1992-11-01
ZA90445B (en) 1990-10-31
US5238586A (en) 1993-08-24
ATE90120T1 (de) 1993-06-15
BR9007045A (pt) 1991-10-08
ES2044555T3 (es) 1994-01-01
KR910700377A (ko) 1991-03-15
AU4951590A (en) 1990-08-13
CA2008361A1 (fr) 1990-07-23
EP0454741A1 (fr) 1991-11-06
EP0379923A1 (fr) 1990-08-01
WO1990008217A1 (fr) 1990-07-26
DE59001626D1 (de) 1993-07-08

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