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WO1999003961A1 - Utilisation de polysaccharides oxydes dans des compositions detergentes - Google Patents

Utilisation de polysaccharides oxydes dans des compositions detergentes Download PDF

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Publication number
WO1999003961A1
WO1999003961A1 PCT/NL1998/000409 NL9800409W WO9903961A1 WO 1999003961 A1 WO1999003961 A1 WO 1999003961A1 NL 9800409 W NL9800409 W NL 9800409W WO 9903961 A1 WO9903961 A1 WO 9903961A1
Authority
WO
WIPO (PCT)
Prior art keywords
polysaccharide
oxidation
use according
polycarboxy
degree
Prior art date
Application number
PCT/NL1998/000409
Other languages
English (en)
Inventor
Cornelis Gerardus Van De Watering
Hermanna Anthonia Angenita Helena Visser
Johannes Wilhelmus Timmermans
Theodoor Maximiliaan Slaghek
Rik Julia Raoul Langerock
Original Assignee
Instituut Voor Agrotechnologisch Onderzoek (Ato-Dlo)
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 Instituut Voor Agrotechnologisch Onderzoek (Ato-Dlo) filed Critical Instituut Voor Agrotechnologisch Onderzoek (Ato-Dlo)
Priority to AU84659/98A priority Critical patent/AU8465998A/en
Priority to EP98935395A priority patent/EP1002036A1/fr
Priority to CA002295481A priority patent/CA2295481A1/fr
Priority to JP2000503169A priority patent/JP2001510232A/ja
Publication of WO1999003961A1 publication Critical patent/WO1999003961A1/fr

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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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/12—Water-insoluble compounds
    • C11D3/124—Silicon containing, e.g. silica, silex, quartz or glass beads
    • C11D3/1246—Silicates, e.g. diatomaceous earth
    • C11D3/128—Aluminium silicates, e.g. zeolites
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/223—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin oxidised

Definitions

  • the invention relates to the use of polycarboxy polysaccharides in detergent compositions.
  • Detergent compositions contain a builder to neutralise the effect of water hardness, dissolution of soil and the like.
  • phosphate is an effective builder, its use is undesired for environmental reasons.
  • Zeolites have largely replaced phosphates as builder.
  • they require the presence of a cobuilder which prevents the redeposition of soil and the precipitation of calcium carbonate, and improves whiteness of the washed laundry.
  • Synthetic polymers, such as polyacrylates have found extensive use as cobuilders, but they are poorly biodegradable. Thus there is need for biodegradable and yet effective cobuilder materials for use in textile washing compositions, dish-washing compositions and the like.
  • EP- A- 755944 discloses a method for the production of oxidising maltodextrins having a DE (dextrose equivalent) between 2 and 20, especially a DE of 11-14, using oxygen or hydrogen peroxide under alkaline conditions in the absence of a catalyst followed by bleaching. This oxidation results in conversion of the reducing end groups in arabinonic acid groups.
  • the product can be used as a cobuilder in detergent compositions wherein it improves whiteness and reduces inorganic incrustation, or as a binder or thickening agent.
  • dicarboxylic polysaccharides such as dicarboxy starch and dicarboxy amylodextrins as a calcium sequestering agent has been described in various documents, e.g. Kohn and Tihlarik, Coll. Czech. Chem. Commun. 49 (1984) 2116, EP-A-427349 and NL-A-8802907.
  • the polysaccharides to be oxidised according to the invention are primarily starch and starch derivatives such as hydrolysed starch and carboxymethyl starch.
  • Other glucans such as cellulose derivatives, 1,3-glucans or 1,6-glucans, galactomannans (e.g. guar) and other vegetal and bacterial gums, can also be used. These have molecular weights of 1600-12,000 (10-75 anhydromonose units), preferably of 2000-10,000 (12-60 amu's), most preferably 2900-7300 (18-40 amu's).
  • Other classes of suitable poly-saccharides are fructans (e.g.
  • inulin which can be used with molecular weights from about 240 upwards, especially 500-12,000, more preferably 1600-5000 (10-30 amu's), and pentosans, such as xylans (hemicellulose), e.g. from waste carbohydrates, with molecular weights of 1500-12,000, preferably 2000-8000, most preferably 2600- 6600 (20-50 amu's).
  • the degree of oxidation is preferably from 0.12 to 0.6, preferably from 0.15 to 0.55, especially form 0.2 to 0.5.
  • the oxidised polysaccharides are preferably obtained by treatment of the poly- saccharide (e.g. starch) with a hypochlorite solution at pH 7.5-10, especially at pH 8-9, the hypochlorite being added gradually in order to be able to maintain the pH more or less constant by addition of a base.
  • the reaction temperature can be e.g. between 0 and 40 °C, especially at ambient temperature.
  • the oxidised product can be isolated by known techniques, including ethanol precipitation and freeze-drying. Such precipitation has the advantage of removing products that have excessive degrees of oxidation.
  • C2-C3 oxidation of glucans, mannans, xylans etc. are also suitable, for example oxidation with periodate (cf. WO 95/12619 or Nieuwenhuizen et al, StarchlSt ⁇ rke, 37 (1985) 192-200), followed by chlorite oxidation.
  • Other oxidations can also be used, e.g. oxidation with hydrogen peroxide in the presence of acetylated polysaccharides, or oxidation with hydrogen peroxide in the presence of copper and magnesium or other oxidation catalysts.
  • Combinations of oxidation processes may also be used.
  • a hydrolysis step (acid or enzymatic) may precede or follow the oxidation step.
  • the invention also pertains to detergent compositions containing a polycarboxy polysaccharide as described above as a cobuilder, anti-redeposition agent and/or soil dispersant.
  • the composition contains 0.5-5 wt.% of the cobuilder prepared according to the invention, and further a detergent (12-25, especially 16-20 wt.%), a zeolite or silicate builder (15-30, especially 20-28 wt.%), a carboxylate such as sodium citrate (3-5 wt.%), a bleaching agent such as sodium perborate (10-20 wt.%), a catalyst such as TAED (3-4 wt.%), and optional further components such as enzymes (about 1-2 %: amylases, proteases), foaming or defoaming agents, odorants and the like.
  • Starch was oxidised generally according to Floor, "Oxidation of maltodextrins and starch with alkaline sodium hypochlorite", Thesis, Chapter 6, Delft (NL), 1989, as follows: 75 g of potato starch was suspended in 250 ml water. The pH was adjusted to 8.5. The appropriate amount of sodium hypochlorite solution (4% or 16% active chlorine) was added at a rate of 10 ml/min for the first half hour and 20 ml/min afterwards for 4 % Cl 2 (2.5 and 5 ml/min, respectively, for 15% CI2) at ambient temperature. The pH was maintained at 8.5 by the addition of 5 M NaOH. After 20 h the pH was adjusted to 9 and 500 ml of ethanol 98% was added.
  • the suspension was stored at -4°C for 16 h and then decanted.
  • the precipitate was dissolved in 150 ml water and 300 ml of ethanol was added.
  • the suspension was again stored at -4°C for 16 h and then decanted.
  • the precipitate was dissolved in 150 ml water and the solution was freeze-dried.
  • DCS-1 Paselli 6 (molecular weight of native starch reduced by a factor 6), 550 ml 4% Cl 2 , dicarboxy content 9% (carboxyl content 0.36 per anhydromonose unit), MW about 5400;
  • DCS-2 Paselli 2, 500 ml 15% Cl 2 , dicarboxy content 19% (carboxyl content 0.48), MW about 3200;
  • DCS-3 native potato starch, 390 ml 15% Cl , dicarboxy content 18% (carboxyl content 0.36), MW about 4700;
  • DCS-4 native potato starch, 500 ml 15% Cl 2 , dicarboxy content 21% (carboxyl content 0.48), MW about 3600.
  • Example 3 Wash tests Two co-builders were tested in a standard heavy duty formulation (HDF: see table 1) during 25 wash cycles using the 60°C cotton washing programme without prewash.
  • product R HDF with reference cobuilder Sokalan CP 5 (a commercial polyacrylate cobuilder)
  • the washing tests were carried out in commercial drum-type domestic washing machines Miele Novotronic W 918.
  • the test of each product was made in alternating machines, in order to avoid effects caused by specific differences of the machines.
  • the tests were carried out at a water hardness of 2.86 mmol/1 in a 60°C cotton programme without prewash.
  • the total machine load was 4.5 kg.
  • the dosage of formulation was 80 g per wash.

Landscapes

  • 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)
  • Health & Medical Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)

Abstract

Polysaccharides polycarboxy, en particulier dicarboxymaltodextrines, dont le poids moléculaire est situé entre 1.600 et 12.000 et dont le degré d'oxydation (DO) est de 0,12 à 0,6 groupe carboxyle par unité d'anhydromonose, qui peuvent être utilisés comme co-adjuvant, en particulier comme agent d'antiredéposition et comme agent de dispersion de la saleté dans des compositions détergentes.
PCT/NL1998/000409 1997-07-15 1998-07-15 Utilisation de polysaccharides oxydes dans des compositions detergentes WO1999003961A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU84659/98A AU8465998A (en) 1997-07-15 1998-07-15 Use of oxidised polysaccharides in detergent compositions
EP98935395A EP1002036A1 (fr) 1997-07-15 1998-07-15 Utilisation de polysaccharides oxydes dans des compositions detergentes
CA002295481A CA2295481A1 (fr) 1997-07-15 1998-07-15 Utilisation de polysaccharides oxydes dans des compositions detergentes
JP2000503169A JP2001510232A (ja) 1997-07-15 1998-07-15 洗剤組成物における酸化された多糖の使用

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP97202196.8 1997-07-15
EP97202196A EP0892041A1 (fr) 1997-07-15 1997-07-15 Utilisation des polysaccharides oxydés dans les compositions détergentes

Publications (1)

Publication Number Publication Date
WO1999003961A1 true WO1999003961A1 (fr) 1999-01-28

Family

ID=8228559

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL1998/000409 WO1999003961A1 (fr) 1997-07-15 1998-07-15 Utilisation de polysaccharides oxydes dans des compositions detergentes

Country Status (5)

Country Link
EP (2) EP0892041A1 (fr)
JP (1) JP2001510232A (fr)
AU (1) AU8465998A (fr)
CA (1) CA2295481A1 (fr)
WO (1) WO1999003961A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7727945B2 (en) 2005-07-15 2010-06-01 Akzo Nobel N.V. Modified polysaccharides
WO2009122953A1 (fr) * 2008-03-31 2009-10-08 花王株式会社 Procédé de fabrication de polyuronate
JP5544107B2 (ja) * 2008-03-31 2014-07-09 花王株式会社 高分子ビルダー
JP2009263641A (ja) * 2008-03-31 2009-11-12 Kao Corp ポリウロン酸塩の製造方法
US9376648B2 (en) 2008-04-07 2016-06-28 The Procter & Gamble Company Foam manipulation compositions containing fine particles
DE102008053607A1 (de) * 2008-10-20 2010-04-22 Südzucker AG Mannheim/Ochsenfurt Solubilisierungsmittel für Metallionen
FR2961394B1 (fr) * 2010-06-21 2012-06-01 Oreal Composition cosmetique comprenant au moins un polysaccharide oxyde non cationique et une huile, de preference polaire
WO2015138283A1 (fr) * 2014-03-11 2015-09-17 E. I. Du Pont De Nemours And Company Poly(alpha-1,3-glucane) oxydé en tant qu'adjuvant pour détergent
JP7296404B2 (ja) * 2018-05-23 2023-06-22 ダウ グローバル テクノロジーズ エルエルシー 自動食器洗浄用無水配合物
WO2020011764A1 (fr) * 2018-07-09 2020-01-16 Koninklijke Coöperatie Cosun U.A. Composition d'anti-tartre comprenant un polysaccharide d'acide uronique

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL8802907A (nl) * 1988-11-25 1990-06-18 Avebe Coop Verkoop Prod Werkwijze voor het vervaardigen van dicarboxypolysacchariden.
EP0427349A2 (fr) * 1989-11-10 1991-05-15 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Procédé pour la préparation de polydicarboxysaccharides
EP0472042A1 (fr) * 1990-08-13 1992-02-26 NOVAMONT S.p.A. Agents séquestrants du calcium à base de carbohydrates oxydés et leur utilisation comme renforçateurs pour détergents
WO1993008251A1 (fr) * 1991-10-23 1993-04-29 Henkel Kommanditgesellschaft Auf Aktien Produit de lavage et de nettoyage a systemes selectionnes d'adjuvants
EP0542496A1 (fr) * 1991-11-14 1993-05-19 The Procter & Gamble Company Amidon oxydé à C6/C2-C3 utilisé comme ingrédient pour détergent
EP0548399A1 (fr) * 1991-12-23 1993-06-30 Cerestar Holding B.V. Méthode de préparation d'acides contenant de l'oxygène à partir d'hydrates de carbone
WO1995012619A1 (fr) * 1993-11-04 1995-05-11 Instituut Voor Agrotechnologisch Onderzoek (Ato-Dlo) Procede d'oxydation de glucides
EP0755944A2 (fr) * 1995-07-11 1997-01-29 Cerestar Holding Bv Composition d'acide polyhydroxycarboxylique à partir de maltodextrines par oxydation avec un oxydant contenant de l'oxygène

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL8802907A (nl) * 1988-11-25 1990-06-18 Avebe Coop Verkoop Prod Werkwijze voor het vervaardigen van dicarboxypolysacchariden.
EP0427349A2 (fr) * 1989-11-10 1991-05-15 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Procédé pour la préparation de polydicarboxysaccharides
EP0472042A1 (fr) * 1990-08-13 1992-02-26 NOVAMONT S.p.A. Agents séquestrants du calcium à base de carbohydrates oxydés et leur utilisation comme renforçateurs pour détergents
WO1993008251A1 (fr) * 1991-10-23 1993-04-29 Henkel Kommanditgesellschaft Auf Aktien Produit de lavage et de nettoyage a systemes selectionnes d'adjuvants
EP0542496A1 (fr) * 1991-11-14 1993-05-19 The Procter & Gamble Company Amidon oxydé à C6/C2-C3 utilisé comme ingrédient pour détergent
EP0548399A1 (fr) * 1991-12-23 1993-06-30 Cerestar Holding B.V. Méthode de préparation d'acides contenant de l'oxygène à partir d'hydrates de carbone
WO1995012619A1 (fr) * 1993-11-04 1995-05-11 Instituut Voor Agrotechnologisch Onderzoek (Ato-Dlo) Procede d'oxydation de glucides
EP0755944A2 (fr) * 1995-07-11 1997-01-29 Cerestar Holding Bv Composition d'acide polyhydroxycarboxylique à partir de maltodextrines par oxydation avec un oxydant contenant de l'oxygène

Also Published As

Publication number Publication date
JP2001510232A (ja) 2001-07-31
AU8465998A (en) 1999-02-10
EP1002036A1 (fr) 2000-05-24
CA2295481A1 (fr) 1999-01-28
EP0892041A1 (fr) 1999-01-20

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