EP0934382B1 - Utilisation de produits de condensation polycationiques comme adjuvants inhibiteurs de transfert de couleurs et reducteurs de decoloration pour les lessives et produits de postlavage - Google Patents

Utilisation de produits de condensation polycationiques comme adjuvants inhibiteurs de transfert de couleurs et reducteurs de decoloration pour les lessives et produits de postlavage Download PDF

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Publication number
EP0934382B1
EP0934382B1 EP97911213A EP97911213A EP0934382B1 EP 0934382 B1 EP0934382 B1 EP 0934382B1 EP 97911213 A EP97911213 A EP 97911213A EP 97911213 A EP97911213 A EP 97911213A EP 0934382 B1 EP0934382 B1 EP 0934382B1
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EP
European Patent Office
Prior art keywords
condensates
piperazine
alkyl group
carbon atoms
weight
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
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EP97911213A
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German (de)
English (en)
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EP0934382A1 (fr
Inventor
Dieter Boeckh
Hans-Ulrich JÄGER
Jürgen Alfred LUX
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BASF SE
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BASF SE
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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • 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
    • C11D3/0021—Dye-stain or dye-transfer inhibiting compositions
    • 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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3723—Polyamines or polyalkyleneimines
    • 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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3776—Heterocyclic compounds, e.g. lactam

Definitions

  • EP-A-0209787 describes a process for the aftertreatment of colored Cellulose fiber materials are known to work with reactive dyes were colored, using either the colored materials discontinuously in the dyeing apparatus or continuously for roving in liss recipients or surface goods on foulards or wide washing machines with an aqueous liquor of benzylated condensation products from piperazine (derivatives) and epichlorohydrin for the removal of unfixed hydrolyzed reactive dyes aftertreated by the colored material.
  • Examples of such compounds are the reaction products of n-butyltriglycolamine of the formula H 2 N- (CH 2 -CH 2 -O) 3 -C 4 H 9 with methyl dodecanoate or the reaction products of ethyl tetraglycolamine of the formula H 2 N- (CH 2 -CH 2 -O) 4 -C 2 H 5 with a commercially available mixture of saturated C 8 - to C 18 -fatty acid methyl esters.
  • the inorganic builders can be used in detergents in quantities from 0 to 60% by weight together with those which may be used organic cobuilders.
  • the inorganic builder can either alone or in any combination with each other be incorporated into the detergent.
  • the detergents contain as a component (iii) 0.05 to 2.5, preferably 0.1 to 1.0% by weight at least one of the cationic condensation products described above.
  • the laundry after-treatment agents contain as component (ii) for example 1 to 50, preferably 2 to 20% by weight of one nonionic surfactant.
  • Nonionic surfactants were used in the Composition of the detergent as component (i) already described.
  • the compounds mentioned there can also be used in Laundry after-treatment agents are used.
  • the laundry aftertreatment contain as component (iii) 0.1 to 2.5, preferably 0.2 to 2.0% by weight of a polycationic condensation product as a color fixing additive. These condensation products have already been described above.
  • Polycationic condensation product obtained by condensing Piperazine with epichlorohydrin in a molar ratio of 1: 1 and through Quaternization of the reaction product with 1.4 mol equivalents Benzyl chloride, based on piperazine, was prepared.
  • the molecular weight was 3500 (determined by viscosity measurement in 1% aqueous solution at 20 ° C).
  • the cationic condensation product was in the form of a 24% aqueous solution.
  • Polycationic condensation product obtained by the reaction of Imidazole, piperazine and epichlorohydrin in a molar ratio of 1: 1: 2 was produced.
  • the aqueous polymer solution contained 50% of the cationic condensation product, which has a molecular weight of 2200 would have.
  • Polycationic condensation product obtained by the reaction of Imidazole and epichlorohydrin in a molar ratio of 1: 1 in aqueous Solution was prepared.
  • the polymer solution contained 50% of the Condensation product that had a molecular weight of 1400.
  • polycationic condensation product obtained by heating Triethanolamine in the presence of 0.5% by weight of hypophosphorous acid to 230 ° C and quaterination with 0.8 molar equivalents of benzyl chloride was produced.
  • the molecular weight was 4500.
  • Color loss [%] 100 ⁇ color strength (before washing) - color strength (after washing) color strength (before washing) test conditions: apparatus Launder-o-meter colored fabric 1.0 g dyed cotton fabric, Colorings with direct red 212 (3% dye) and Direct blue 71 (0.8% dye) White fabric 2.5 g cotton fabric pretreatment: softener Softlan® (manufacturer Colgate Polmolive) Use concentration of the polymers in the fabric softener: 2.0% Amount of fabric softener: 1.75 g / l Temperature (rinsing): 30 ° C Rinsing time: 10 min.
  • Laundry laundry detergent Ajax® (manufacturer Colgate-Palmolive) quantity 5.0 g / l amount of liquor 250 g wash temperature 40 ° C water hardness 14.5 ° dH Ca / Mg ratio 4.0: 1.0 washing time 30 min.
  • Polymer 1 was added to the above fabric softener in an amount added by 2%.
  • the color transfer inhibiting effect in% of a fabric stained with Direct Blue 71 was 99%.
  • the color loss in% of that stained with Direct Blue 71 After 5 washes, the fabric was with the detergent specified above 7.2%.
  • Example 1 was repeated, but in the absence of polymer 1 worked.
  • the color transfer inhibiting effect was 0%.
  • the color loss after 5 washes for one with direct Blue 71 dyed fabric was 20.3%.
  • Example 1 was repeated with 2% polymer 4. The color transfer inhibiting effect was 98% and the color loss was 8.4%. Trials with direct red 212 Polycationic condensation product Color transfer inhibition [%] Color loss [%] example kind Quantity [%] in Softlan® 3 Polymer 1 2 100 11.3 4 Polymer 2 2 95.1 18.9 5 Polymer 3 2 93.8 15.4 Comp. 2 - 0 30.3
  • the color transfer inhibiting effect was determined after one wash, the color change after 5 washes each based on the color strengths of the white fabric or the color fabric such as described for use in fabric softener.
  • the color transfer-inhibiting effect was tested in various heavy-duty detergents and color detergents (Tables 3 and 4).
  • the polycationic condensation products show a marked reduction in color transfer and a reduction in color separation I II III IV V VI VII Polymer 1 1.5 1.0 0.5 0.6 0.3 Polymer 2 1.0 Polymer 3 1.0 AS / MS (70000) 7.5 6.0 5.0 5.0 4.0 AS / MS / VAc terpolymer (40000) 5.0 Na perborate monohydrate 15 15 15 7.5 Na Percarbonate 18 15 18 TAED 4.0 3.8 5.0 5.0 2.9 4.2 2.0 Na lauryl sulfate 1.0 linear alkyl benzene sulfonate Na salt 0.8 sulfated fatty alcohol ethoxylate 1.5 Korantin®SH 3.1 2.0 Soap 0.4 2.5 1.5 2.4 C 13 / C 15 oxo alcohol * 3 EO 3.0
  • Table 4 shows the composition of color detergents which contain cationic condensation products to be used according to the invention.
  • VII VIII IX X XI XII Polymer 1 1.0 1.0 0.5 1.0 0.5 0.3 AS / MS (70000) 6.0 4.0 3.5 2.0 2.5 8.5 Na lauryl sulfate 12 sulfated fatty alcohol ethoxylate 1.5 Korantin®SH 2.0 Soap 2.5 1.0 1.5 1.5 C 13 / C 15 oxo alcohol * 3 EO 10.0 1.5 C 13 / C 15 oxo alcohol * 7 EO 6.7 16.0 13.5 14.0 7.5 C 13 / C 15 oxo alcohol * 10 EO 6.3 Lauryl alcohol * 13 EO 2.0 9.0 Zeolite A 28 55 35 37 18 Zeolite P 36 SKS-6 12 Na disilicate 4.5 0.5 4.5 Mg silicate 1.0 1.0 sodium sulphate 24 5.8 11.5 8.0 4.5 10.0 sodium 6.5 6.5 sodium 12.0 6.0 10.0 9.0 carboxymethylcellulose 0.6 0.5

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

Claims (9)

  1. Mise en oeuvre de produits de condensation polycationiques que l'on peut obtenir au moyen d'une condensation de
    (a) la pipérazine, les 1-alkylpipérazines présentant 1 à 25 atomes de C dans le groupe alkyle, les 1,4-dialkylpipérazines présentant 1 à 25 atomes de C dans le groupe alkyle, la 1,4-bis-(3-aminopropyl)-pipérazine, la 1-(2-aminoéthyl)pipérazine, les 1-(2-hydroxyalkyl)pipérazines présentant 2 à 25 atomes de C dans le groupe alkyle, l'imidazole, les imidazoles d'alkyle en C1 à C25 ou les mélanges des composés cités, avec
    (b) les dihalogénures d'alcène, les épihalogénohydrines et/ou les bis-époxydes
    dans un rapport molaire compris entre 1:0,8 et 1:1,1 et éventuellement une quaternisation des produits de condensation avec des agents d'alkylation en C4 à C25,
    ou au moyen d'un chauffage de la triéthanolamine ou de la triisopropanolamine en présence de catalyseurs acides, et une quaternisation des produits de condensation à l'aide des agents d'alkylation en C4 à C25,
    en tant qu'adjuvants inhibiteurs de transfert de couleurs et réducteurs de décoloration pour les lessives et produits de postlavage.
  2. Mise en oeuvre selon la revendication 1, caractérisée en ce que l'on emploie les produits de condensation que l'on peut obtenir au moyen d'une condensation de
    (a) la pipérazine, la 1-(2-hydroxyéthyl)pipérazine, la 1-(2-aminoéthyl)pipérazine, l'imidazole, les (C-alkyle en C1 à C3)imidazoles ou les mélanges des composés cités avec
    (b) le 1,2-dichloroéthane, le 1,2-dichloropropane, le 1,3-dichloropropane, le 1,4-dichlorobutane, l'épichlorhydrine, le bis-époxybutane ou les mélanges des composés cités,
    et éventuellement
    (c) une quaternisation des produits de condensation avec les halogénures d'alkyle en C6 à C22 ou les époxydes en C8 à C22, ou au moyen d'un chauffage de la triéthanolamine ou de la triisopropanolamine avec les catalyseurs acides et une quaternisation des produits de condensation avec les halogénures d'alkyle en C6 à C22 ou les époxydes en C8 à C22.
  3. Mise en oeuvre selon la revendication 1 ou 2, caractérisée en ce que l'on emploie pour procéder à la quaternisation des produits de condensation, en tant que composés du groupe (c), le chlorure de benzyle et/ou l'oxyde de styrène.
  4. Mise en oeuvre selon la revendication 1 ou 2, caractérisée en ce que les produits de condensation présentent une masse molaire comprise entre 500 et 100 000.
  5. Mise en oeuvre selon la revendication 1 ou 2, caractérisée en ce que les produits de condensation présentent une masse molaire comprise entre 1 000 et 50 000.
  6. Mise en oeuvre selon l'une quelconque des revendications 1 à 5, caractérisée en ce que le degré de quaternisation des groupes amino des produits de condensation est d'au moins 25%.
  7. Mise en oeuvre selon l'une quelconque des revendications 1 à 6, caractérisée en ce que le degré de quaternisation des groupes amino des produits de condensation est d'au moins 50%.
  8. Mise en oeuvre selon l'une quelconque des revendications 1 à 7, caractérisée en ce que le degré de quaternisation des groupes amino des produits de condensation est compris entre 70% et 100%.
  9. Produit de postlavage, caractérisé en ce qu'il contient
    (i) un produit assouplissant pour textiles, à raison de 1% à 50% en poids,
    (ii) un agent tensio-actif non ionique, à raison de 1% à 50% en poids, et
    (iii) un produit de condensation polycationique, à raison de 0,1% à 2,5% en poids, que l'on peut obtenir au moyen d'une condensation de
    (a) la pipérazine, les 1-alkylpipérazines présentant 1 à 25 atomes de C dans le groupe alkyle, les 1,4-dialkylpipérazines présentant 1 à 25 atomes de C dans le groupe alkyle, la 1,4-bis-(3-aminopropyl)-pipérazine, la 1-(2-aminoéthyl)pipérazine, les 1-(2-hydroxyalkyl)pipérazines présentant 2 à 25 atomes de C dans le groupe alkyle, l'imidazole, les (C-alkyle en C1 à C25)imidazoles ou les mélanges des composés cités, avec
    (b) les dihalogénures d'alcène, les épihalogénohydrines et/ou les bis-epoxydes
    dans un rapport molaire compris entre 1:0,8 et 1:1,1 et éventuellement une quaternisation des produits de condensation avec des agents d'alkylation en C4 à C25, ou au moyen d'un chauffage de la triéthanolamine ou de la triisopropanolamine en présence de catalyseurs acides, et une quaternisation des produits de condensation à l'aide des agents d'alkylation en C4 à C25.
EP97911213A 1996-10-21 1997-10-10 Utilisation de produits de condensation polycationiques comme adjuvants inhibiteurs de transfert de couleurs et reducteurs de decoloration pour les lessives et produits de postlavage Expired - Lifetime EP0934382B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19643281 1996-10-21
DE19643281A DE19643281A1 (de) 1996-10-21 1996-10-21 Verwendung von polykationischen Kondensationsprodukten als farbfixierenden Zusatz zu Waschmitteln und Wäschenachbehandlungsmitteln
PCT/EP1997/005606 WO1998017762A1 (fr) 1996-10-21 1997-10-10 Utilisation de produits de condensation polycationiques comme adjuvants inhibiteurs de transfert de couleurs et reducteurs de decoloration pour les lessives et produits de postlavage

Publications (2)

Publication Number Publication Date
EP0934382A1 EP0934382A1 (fr) 1999-08-11
EP0934382B1 true EP0934382B1 (fr) 2002-12-18

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EP97911213A Expired - Lifetime EP0934382B1 (fr) 1996-10-21 1997-10-10 Utilisation de produits de condensation polycationiques comme adjuvants inhibiteurs de transfert de couleurs et reducteurs de decoloration pour les lessives et produits de postlavage

Country Status (7)

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US (3) US6025322A (fr)
EP (1) EP0934382B1 (fr)
JP (1) JP4294734B2 (fr)
AT (1) ATE230010T1 (fr)
DE (2) DE19643281A1 (fr)
ES (1) ES2188915T3 (fr)
WO (1) WO1998017762A1 (fr)

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Publication number Priority date Publication date Assignee Title
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US8530403B2 (en) * 2009-11-20 2013-09-10 Ecolab Usa Inc. Solidification matrix using a maleic-containing terpolymer binding agent
US20110124547A1 (en) * 2009-11-23 2011-05-26 Ecolab Inc. Solidification matrix using a sulfonated/carboxylated polymer binding agent
BR112012026685B1 (pt) 2010-04-22 2020-01-14 Unilever Nv uso de um polímero catiônico no tratamento de têxteis para a fixação do corante em têxteis
WO2012117024A1 (fr) * 2011-03-01 2012-09-07 Basf Se Polymères actifs dans l'inhibition de transfert de couleurs et présentant une durée de conservation accrue et une aptitude à la mise en oeuvre améliorée pour des produits de lavage et de nettoyage
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US6465415B2 (en) 2002-10-15
ATE230010T1 (de) 2003-01-15
US6025322A (en) 2000-02-15
DE19643281A1 (de) 1998-04-23
JP4294734B2 (ja) 2009-07-15
US20020045563A1 (en) 2002-04-18
ES2188915T3 (es) 2003-07-01
DE59709029D1 (de) 2003-01-30
US6262011B1 (en) 2001-07-17
WO1998017762A1 (fr) 1998-04-30
EP0934382A1 (fr) 1999-08-11
JP2001503089A (ja) 2001-03-06

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