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EP0379923A1 - Agent de traitement de textile - Google Patents

Agent de traitement de textile Download PDF

Info

Publication number
EP0379923A1
EP0379923A1 EP90100742A EP90100742A EP0379923A1 EP 0379923 A1 EP0379923 A1 EP 0379923A1 EP 90100742 A EP90100742 A EP 90100742A EP 90100742 A EP90100742 A EP 90100742A EP 0379923 A1 EP0379923 A1 EP 0379923A1
Authority
EP
European Patent Office
Prior art keywords
textile treatment
mol
amino groups
treatment agent
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.)
Withdrawn
Application number
EP90100742A
Other languages
German (de)
English (en)
Inventor
Günter Uphues
Uwe Dr. 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
Publication of EP0379923A1 publication Critical patent/EP0379923A1/fr
Withdrawn legal-status Critical Current

Links

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.
  • German patent 19 22 046 describes detergents containing fatty acid condensation products which contain fatty acid partial glycerides which have a dispersing action; German patent specification 19 22 047 also 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.
  • a textile treatment agent which can be prepared by reacting a) aliphatic monocarboxylic acids having 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 added if desired and the natural and synthetic hydrophilic polymers, characterized in that the unreacted amino groups are neutralized to 20 to 80 mol%, in particular to 30 to 60 mol%. In contrast to the complete neutralization with stoichiometric or excess amounts of acids, this partial neutralization with
  • 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-distearylammonium 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 especially 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 agents 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 containing 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 20 to 80 mol%, preferably to 30 to 60 mol%.
  • 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 according to the invention in such an amount as is necessary for the 20 to 80 mol%, preferably 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.
  • 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 according to the invention When used in detergents, they bring about an improved cleaning effect and / or a softening of the laundry washed therewith.
  • textile treatment agents according to the invention 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 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. When the acid number reached 4, 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 at 90-100 ° C. with 11.8 g (0.105 mol) of milk acid, 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 mole) lactic acid, 80%, was neutralized to about 100 mole%.
  • Table 1 product Assessment of the degree of dispersity Swelling after stirring after 1 hour after 24 hours LW ve LW ve LW ve LW ve Example 1a 2nd 2nd 2nd 1/2 1 1 1 Example 1b 2nd 2nd 2/3 2nd 2nd 1 1 1 Example 1c 2nd 2nd 1/2 1/2 1 1 1 1 1 Example 1d 3rd 3rd 3rd 3rd 2/3 2nd 2nd 1 Example 2a 3rd 3/4 3rd 3rd 2nd 2nd 1/2 Example 2b 4th 3/4 3/4 3/4 3rd 3rd 2/3 2nd Example 2c 3rd 3rd 2/3 3rd 2nd 2/3 1 1 Example 2d 5 4/5 3/5 3/5 3/5 3/5 3rd 3rd Example 3 4/5 5 3/5 3/5 3/4 3/4 3/4 3/4 3/4 Example 4 2/3 2/3 2/3 2nd 1/2 1/2 Example 5 3rd 2/3 2/3 2nd 2nd 1/2 1/2 Example 5 3rd 2/3 2/3 2nd 2nd 1/2 1/2 Example 5 3rd 2/3 2/3 2nd 1/2 1/2 Example 5 3rd 2
  • Hardened terry toweling (approx. 60 g / sample) was treated in a wacker vessel on a roller bench with a liquor which contained the products in Table 2 in the form of 5% dispersions. The same standard conditions were chosen for all tests: Water hardness: approx. 16 ° dH Fleet ratio: 1:10 Amount used: 0.15% active ingredient based on tissue Temperature: 15 ° C Treatment time: 5 minutes

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Detergent Compositions (AREA)
  • Polyamides (AREA)
EP90100742A 1989-01-23 1990-01-15 Agent de traitement de textile Withdrawn EP0379923A1 (fr)

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 (1)

Publication Number Publication Date
EP0379923A1 true EP0379923A1 (fr) 1990-08-01

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 Before (1)

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

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)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992018685A1 (fr) * 1991-04-10 1992-10-29 Henkel Kommanditgesellschaft Auf Aktien Produit de traitement des textiles a dispersibilite amelioree dans l'eau
WO1994024092A1 (fr) * 1993-04-13 1994-10-27 Henkel Kommanditgesellschaft Auf Aktien Amides d'acides gras a dispersibilite dans l'eau froide amelioree

Families Citing this family (6)

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

Citations (5)

* 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
EP0038862A1 (fr) * 1979-08-03 1981-11-04 Albright & Wilson Limited Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles
DE3530302A1 (de) * 1985-08-24 1987-03-05 Henkel Kgaa Textilbehandlungsmittel
DE3601856A1 (de) * 1986-01-23 1987-07-30 Henkel Kgaa Textilbehandlungsmittel
DE3730792A1 (de) * 1987-09-14 1989-03-23 Henkel Kgaa Textilbehandlungsmittel

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP0300098B1 (fr) * 1987-07-21 1991-11-21 Agfa-Gevaert N.V. Méthode d'enduction

Patent Citations (5)

* 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
EP0038862A1 (fr) * 1979-08-03 1981-11-04 Albright & Wilson Limited Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles
DE3530302A1 (de) * 1985-08-24 1987-03-05 Henkel Kgaa Textilbehandlungsmittel
DE3601856A1 (de) * 1986-01-23 1987-07-30 Henkel Kgaa Textilbehandlungsmittel
DE3730792A1 (de) * 1987-09-14 1989-03-23 Henkel Kgaa Textilbehandlungsmittel

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992018685A1 (fr) * 1991-04-10 1992-10-29 Henkel Kommanditgesellschaft Auf Aktien Produit de traitement des textiles a dispersibilite amelioree dans l'eau
WO1994024092A1 (fr) * 1993-04-13 1994-10-27 Henkel Kommanditgesellschaft Auf Aktien Amides d'acides gras a dispersibilite dans l'eau froide amelioree

Also Published As

Publication number Publication date
DE59001626D1 (de) 1993-07-08
DE3901820A1 (de) 1990-08-09
AU4951590A (en) 1990-08-13
JPH04503088A (ja) 1992-06-04
CA2008361A1 (fr) 1990-07-23
US5238586A (en) 1993-08-24
ZA90445B (en) 1990-10-31
BR9007045A (pt) 1991-10-08
EP0454741B1 (fr) 1993-06-02
ES2044555T3 (es) 1994-01-01
EP0454741A1 (fr) 1991-11-06
ATE90120T1 (de) 1993-06-15
KR970011243B1 (ko) 1997-07-08
KR910700377A (ko) 1991-03-15
WO1990008217A1 (fr) 1990-07-26
TR25133A (tr) 1992-11-01

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