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WO1993008254A1 - Composition granulaire d'activateurs de blanchiment - Google Patents

Composition granulaire d'activateurs de blanchiment Download PDF

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Publication number
WO1993008254A1
WO1993008254A1 PCT/EP1992/002178 EP9202178W WO9308254A1 WO 1993008254 A1 WO1993008254 A1 WO 1993008254A1 EP 9202178 W EP9202178 W EP 9202178W WO 9308254 A1 WO9308254 A1 WO 9308254A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
activator composition
bleach activator
composition according
granular
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.)
Ceased
Application number
PCT/EP1992/002178
Other languages
German (de)
English (en)
Inventor
Reinhard Mueller
Guenter Oetter
Alfred Oftring
Volker Schwendemann
Wolfgang Trieselt
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of WO1993008254A1 publication Critical patent/WO1993008254A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3935—Bleach activators or bleach catalysts granulated, coated or protected
    • 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
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing compounds
    • C11D3/392—Heterocyclic compounds, e.g. cyclic imides or lactames

Definitions

  • the present invention relates to a new granular bleach activator composition comprising 4H-3, 1-benzoxazin-4-one derivatives, optionally further conventional bleach activators and additives.
  • the invention further relates to a method for producing this bleach activator composition and to detergents and cleaning agents which contain this granular bleach activator composition.
  • bleach activators including 4H-3, 1-benzoxazin-4-one derivatives, have insufficient water solubility, especially in the temperature range between 25 and 60 ° C, and are in
  • washing powder not sufficiently stable in storage. It is therefore common practice to assemble these bleach activators to increase the rate of dissolution and the effectiveness in the wash liquor and to improve the shelf life.
  • US Pat. No. 4,483,778 (1) relates to a granular peroxy bleach activator composition which contains nonionic surfactants, polyethylene glycols, fatty acids, anionic surfactants or film-forming polymers such as homo- and copolymers of acrylic acid, hydroxyacrylic acid and methacrylic acid or cellulose derivatives as binders or enveloping material.
  • EP-A 062 523 (2) relates to a bleach activator granulate which is produced by extruding a mixture of a low-melting surfactant, a bleach activator such as N, N, N ', N'-tetraacetylethylene diamine and an additive.
  • EP-A 456 109 (3) relates to a process for the preparation of a granular bleach activator composition from pentaacetyl glucose, optionally further conventional bleach activators and additives by reacting glucose with acetic anhydride, removing the acetic acid formed by distillation, and mixing the pentaacetyl glucose thus obtained with the other components and packaging.
  • 4H-3, l-benzoxazin-4-one is also used, only a weight ratio of these compounds to pentaacetyl glucose of 1:99 to 90:10 is disclosed.
  • the known agents of the prior art are also in need of improvement with regard to the rate of dissolution and effectiveness in the washing liquor and the storage stability in the washing powder; in particular, this also applies to 4H-3, l-benzoxazin-4-one derivatives.
  • the object of the present invention was therefore to remedy the disadvantages of the prior art described.
  • R is C 1 ⁇ to C 4 ⁇ al yl or alkoxy, phenyl, o-, m- or p-tolyl, p-chlorophenyl, m-nitrophenyl, m-methoxyphenyl or methylsulfonylphenyl, or a mixture of the Compounds I and other conventional " bleach activators, with the exception of mixtures of 90% by weight or less of the compounds I and 10% by weight or more of pentaacetyl glucose, and
  • Components A and B of the bleach activator composition according to the invention are distributed essentially homogeneously in the mixture.
  • additives B have above all a dispersing function, but can also have a protective function for the bleach activators against, for example, moisture or atmospheric oxygen in the form of coatings.
  • component A can contain, in addition to the compounds I, other conventional bleach activators.
  • Weight ratio of the additional bleach activators to the compounds I is usually 1:99 to 90:10, preferably 1:99 to 50:50.
  • Acyloxybenzenesulfonic acids and their alkali and alkaline earth metal salts e.g. Sodium p-isononanoyloxy-benzenesulfonate or sodium p-benzoyloxy-benzenesulfonate;
  • N-diacylated and N, '-tetraacylated amines e.g. N, N, N ', N'-tetraacetyl-methylenediamine and -ethylenediamine, N, N-diacetylaniline, N, N-diacetyl-p-toluidine or 1,3-diacylated hydantoins such as 1,3-diacetyl-5, 5-dimethylhydantoin;
  • acylated sugars e.g. Pentaacetyl glucose.
  • N-alkyl-N-sulfonyl-carbonamides e.g. N-methyl-N-mesyl-acetamide or N-methyl-N-mesyl-benzamide;
  • N-acylated cyclic hydrazides acylated triazoles or urazoles, e.g. Monoacetyl maleic acid hydrazide;
  • N, N-trisubstituted hydroxylamines e.g. O-benzoyl-N, - succinyl-hydroxyla in, 0-acetyl-N, N-succinyl-hydroxylamine or O, N, N-triacetyl-hydroxylamine;
  • N, N'-diacyl-sulfurylamide for example N, N'-dimethyl-N, N'-di-acetyl-sulfurylamide or N, N'-diethyl-N, N'-di-propionyl-sulfurylamide;
  • Triacyl cyanurates for example triacetyl cyanurate or tribenzoyl cyanurate;
  • Carboxylic anhydrides e.g. Benzoic anhydride, m-chloro-benzoic anhydride or phthalic anhydride;
  • 1,3-diacyl-4,5-diacyloxyimidazolines e.g. 1,3-diacetyl-4,5-diacetoxy-imidazoline;
  • diacylated 2,5-diketopiperazines e.g. 1,4-diacetyl-2,5-diketopiperazine;
  • ⁇ -acyloxy polyacyl malonamides e.g. ⁇ -acetoxy-N, '-diacetylmalonamide
  • Diacyl-dioxohexahydro-1,3,5-triazines e.g. 1,5-diacetyl-2,4-dioxo-hexahydro-l, 3,5-triazine.
  • a preferred granular bleach activator composition consists of
  • Suitable anionic surfactants (1) for B are, for example, alkali metal salts of fatty acids, alkylbenzenesulfonates, alkanesulfonates, ⁇ -olefinsulfonates, hydroxyalkanesulfonates, ⁇ -sulfofatty acid esters, alkyl sulfates, alkyl ether sulfates or fatty alcohol ether sulfates.
  • Alkylbenzenesulfonates in particular the alkali metal and ammonium salts of linear C 1 -C 3 -alkylbenzenesulfonates, for example sodium dodecylbenzenesulfonate, are preferred.
  • Nonionic surfactants (2) for B are, for example, primary or secondary alcohol oxalkylates such as fatty alcohol ethoxylates and alkylphenoloxyalkylates, fatty acid alkylolamides and especially alkyl glycosides, especially C ⁇ - to Cie-monoalkyalkglucosides, for example Cio-monoalkylglucoside.
  • primary or secondary alcohol oxalkylates such as fatty alcohol ethoxylates and alkylphenoloxyalkylates, fatty acid alkylolamides and especially alkyl glycosides, especially C ⁇ - to Cie-monoalkyalkglucosides, for example Cio-monoalkylglucoside.
  • Suitable zwitterionic surfactants (3) for B are, for example, secondary and tertiary amine oxides.
  • Suitable carboxyl group-containing polymers (4) for B are, in particular, homopolymers of acrylic acid and methacrylic acid and copolymers containing acrylic acid and / or methacrylic acid, and the associated alkali metal or ammonium salts.
  • the most advantageous polysaccharides (5) for B are starch, amylose and derivatives of these naturally occurring polysaccharides such as carboxymethyl cellulose, cellulose acetate hydrogen phthalate, ethyl cellulose or sulfated cellulose ethers. Of these, starch itself can best be used.
  • Particularly suitable polyalkylene glycols (6) for B are polyethylene glycols and ethylene oxide-propylene oxide copolymers.
  • Mixtures of several additives B from one of groups (1) to (6) or from different groups can also be used.
  • the granular bleach activator compositions can also contain customary auxiliaries C in the amounts customary for this, customary auxiliaries which, e.g. as disintegrants, dispersants or
  • Packaging aids are used, for example, polymers such as polyvinylpyrrolidone or inorganic salts such as sodium sulfate or sodium triphosphate. Complexing agents such as phosphonates, EDTA or NTA can also be present.
  • the granular bleach activator composition according to the invention additionally contains 0.1 to 30% by weight, in particular 0.1 to 5% by weight, based on the total amount of the composition, of an aliphatic di- or tricarboxylic acid or an aromatic mono- or Dicarboxylic acid, which may additionally contain hydroxyl groups in the molecule, or a mixture thereof.
  • the carboxylic acids mentioned are usually distributed essentially homogeneously in the bleach activator composition according to the invention. This brings about an improvement in color stability when stored in washing powders.
  • Suitable aliphatic di- or tricarboxylic acids and aromatic mono- or dicarboxylic acids which can additionally contain hydroxyl groups in the molecule, are, for example, Oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, maleic acid, fu aric acid, tartaric acid, malic acid, citric acid, benzoic acid, salicylic acid, phthalic acid, ⁇ - and ß-naphthoic acid and naphthalic acid. Adipic acid, tartaric acid, citric acid and benzoic acid are preferred.
  • the invention further relates to a method for producing the granular bleach activator composition according to the invention, which is characterized in that
  • R represents C 1 -C 1 -alkyl or -alkoxy, phenyl, o-, m- or p-tolyl, p-chlorophenyl, m-nitrophenyl, m-methoxyphenyl or m-methylsulfonylphenyl, or a mixture of the compounds I and other customary bleach activators, with the exception of mixtures of 90% by weight or less of the compounds I and 10% by weight or more of pentaacetyl glucose, in the molten state with B) 5 to 70 parts by weight of one or more additives from the substance classes
  • step a further additives and auxiliary substances are mixed (step a) and the resulting mixture is converted into a granular form by packaging (step b).
  • the pure compounds I usually melt in the temperature range from 100 to 200 ° C. If mixtures of the compounds I are used with other conventional bleach activators, this mixture can also melt at lower temperatures. If further bleach activators are used, these can be added to the compounds I before or simultaneously with the additives B.
  • the mixing step (a) of the molten bleach activator component A with the additives B is thus advantageously carried out at temperatures from 60 to 180 ° C., preferably 80 to 150 ° C.
  • the additives B are clearly dissolved or finely dispersed in the melt of A.
  • the preparation (b) is carried out by grinding the solidified melt from bleach activators A and additives B to the desired particle size. All devices customary for this purpose can be used for grinding; are here in particular
  • the melt should be cooled to temperatures below approx. 25 ° C.
  • Preparation (b) by extrusion of the molten mixture of bleach activators A and additives B and subsequent mechanical comminution to the desired particle size. All common extruder types can be used for this; Continuous running in the same direction are preferred
  • Twin-shaft extruder used, they advantageously have a cleaning profile.
  • extruders offers the additional advantage that the mixing step (a) and the finishing step (b) can be carried out in one device.
  • the product crystallized through nozzles to a certain toughness is expediently shaped into continuous filaments in the extruder and, after cooling, comminuted on a cooling belt.
  • the cooling of the melt consisting of components A and B in the extruder is preferably carried out with cooling water of 30 to 70 ° C., so that the toughness of the melt is not too high and thus a good distribution of the individual components after mixing is possible.
  • the cooling must be sufficient to generate enough crystals of germs and to achieve a minimum toughness which only allows extrusion of dimensionally stable threads.
  • Additional cooling and comminution devices can be connected downstream of the extruder.
  • the preparation (b) is carried out by spraying the molten mixture of bleach activators A and additives B to the desired particle size. All the usual devices for this purpose can be used for spraying; Spray towers are particularly worth mentioning here.
  • the embodiments of the preparation by extrusion and by spraying additionally offer the advantage that the melt from components A and B solidifies plastically by supercooling, so that a high rate of dissolution of the grains obtained in water, that is to say also in the washing liquor, can be achieved.
  • the granules are additionally coated with one or more of the additives B or an aliphatic di- or tricarboxylic acid or an aromatic mono following the confectioning (b) - Or dicarboxylic acid, which may additionally contain hydroxyl groups in the molecule, or a mixture thereof.
  • Coating is carried out either by spraying the additives B meltable at low temperature or the carboxylic acids mentioned or by spraying the aqueous solution of these substances over the grains.
  • the coated grains must then be dried.
  • Adipic acid, tartaric acid, citric acid and benzoic acid are used as carboxylic acids.
  • the grains of the composition should have an average diameter of approximately 0.1 to approximately 1 mm, in particular 0.5 to 1 mm.
  • the grains have a prill, granulate, pellet or compact shape.
  • the grains are usually white. They dissolve easily in lukewarm water within a short time and release the bleaching actuator in finely dispersed form.
  • the present invention furthermore relates to washing and cleaning agents which contain 0.5 to 20% by weight, preferably 1 to 10% by weight, of the granular bleach activator composition according to the invention and the customary bleaching agents in the customary amounts.
  • these are textile detergents in powder form, to which the granular bleach activator composition according to the invention is admixed during or after its manufacture, and conventional constituents and compositions of detergents and cleaning agents are known to the person skilled in the art and therefore do not need to be discussed in more detail here.
  • the granular bleach activator composition according to the invention together with the bleach, has a sufficiently high bleaching effect in the wash liquor.
  • the composition dissolves very finely dispersed in the wash liquor in the shortest possible time, even at low temperatures in the range between 20 and 40 ° C, and can thus quickly develop its effect.
  • the disadvantages frequently observed with bleach activator compositions which are too coarse-grained fixation of the grains in the tissue, irregular and spotty bleaching action, destruction of the textile fibers) do not occur.
  • the granular bleach activator composition according to the invention in washing powder is sufficient, i.e. for several months, stable in storage; essentially no discoloration or decomposition processes can be observed.
  • 100 g of solid sodium dodecylbenzenesulfonate were dispersed in 800 g of melted 2-phenyl-4H-3, l-benzoxazin-4-one at 130 ° C.
  • the melt which had cooled to room temperature, was comminuted in a hammer mill to an average particle size of 0.5 to 1 mm.
  • the granules were then coated by spraying on 330 ml of a 30% strength by weight sodium dodecylbenzenesulfonate solution at 80 ° C. and then dried in a fluidized bed dryer at 60 ° C. to a water content of ⁇ 1%.
  • 100 g of water-soluble starch were dispersed in 800 g of melted 2-phenyl-4H-3, l-benzoxazin-4-one at 130 ° C.
  • the melt was sprayed in a spray tower to an average grain size of 0.5 to 1 mm.
  • the granules were then coated by spraying 330 ml of a 30% strength by weight starch solution at 80 ° C. and then dried in a fluidized bed dryer at 60 ° C. to a water content of ⁇ 1%.
  • n-decyl glucoside 300 g were dissolved in 600 g of melted 2-phenyl-4H-3, l-benzoxazin-4-one at 130 ° C.
  • the melt cooled to room temperature, was brought to an average grain size of 0.5 to 1 mm in a hammer mill.
  • the granules were then coated by spraying on 330 ml of a 30% by weight n-decyl glucoside solution at 80 ° C. and then dried in a fluidized bed dryer at 60 ° C. to a water content of ⁇ 1%.
  • Detergent preparations were produced with the granular bleach activator compositions described in Examples 1 to 9, with which just as good or in part even better overall bleaching effects could be achieved as with the same preparations which, instead of the bleach activator composition according to the invention, had the same amount of an agent of the prior art contained.
  • the mixture of the 2-phenyl-4H-3, l-benzoxazin-4-one-containing granules from Examples 2 and 5 to 9 and the powder detergent composition described below was determined for its suitability for textile washing examined, the granules and the powder detergent being mixed so that the bleach activator content of the entire detergent preparation was 4.0% by weight.
  • the Launder-O-meter from Atlas was used as the washing device.
  • the washing time including heating up time was 30 minutes and the liquor ratio was 1: 14.3.
  • R reflectance (measured variable) v: before washing the soiled test fabric n: after washing the soiled test fabric o: before soiling the fabric.
  • the table shows the calculated degrees of bleaching of the test fabrics, each as an average of 3 measured values after washing at 20 ° C., 38 ° C. and 60 ° C.
  • a detergent preparation which contained 4.0% by weight of the listed bleach activator of the prior art was prepared under the same conditions.

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  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (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)

Abstract

Composition granulaire d'activateurs de blanchiment contenant: A) 30 à 95 parties en poids d'au moins un dérivé de 4H-3,1 benzoxanin-4-one de la formule I, dans laquelle R représente un groupe alkyle ou alcoxy C1 à C4, un groupe phényle, un groupe o-tolyle, m-tolyle ou p-tolyle, un groupe p-chlorophényle, un groupe m-nitrophénile, un groupe m-métoxyphényle ou m-méthylsulfonylphényle, ou un mélange de composés de la formule I et d'autres activateurs de blanchiment usuels, à l'exception des mélanges de 90 % en poids ou moins de composés de la formule I et de 10 % en poids ou plus de glucose de pentaacétyle, et B) 5 à 70 parties en poids d'au moins un des additifs des catégories de composés suivantes: 1) tensio-actifs ioniques, 2) tensio-actifs non anioniques, 3) tensio-actifs zwitterioniques, 4) polymères contenant des groupes carboxyliques, 5) polysaccharides, 6) polyalkylèneglycols.
PCT/EP1992/002178 1991-10-22 1992-09-21 Composition granulaire d'activateurs de blanchiment Ceased WO1993008254A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19914134770 DE4134770A1 (de) 1991-10-22 1991-10-22 Koernige bleichaktivatorzusammensetzung
DEP4134770.6 1991-10-22

Publications (1)

Publication Number Publication Date
WO1993008254A1 true WO1993008254A1 (fr) 1993-04-29

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Application Number Title Priority Date Filing Date
PCT/EP1992/002178 Ceased WO1993008254A1 (fr) 1991-10-22 1992-09-21 Composition granulaire d'activateurs de blanchiment

Country Status (3)

Country Link
AU (1) AU2577192A (fr)
DE (1) DE4134770A1 (fr)
WO (1) WO1993008254A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2022551583A (ja) * 2019-10-01 2022-12-12 モレキュラー スキン セラピューティクス，インコーポレイティド Ｋｌｋ５／７デュアル阻害剤としてのベンゾキサジノン化合物

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6759382B2 (en) 2001-06-01 2004-07-06 Kay Chemical, Inc. Detergent composition containing a primary surfactant system and a secondary surfactant system, and a method of using the same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0456109A2 (fr) * 1990-05-10 1991-11-13 BASF Aktiengesellschaft Procédé pour préparer une composition granulaire d'activateur de blanchiment
EP0482806A1 (fr) * 1990-10-23 1992-04-29 WARWICK INTERNATIONAL GROUP LIMITED (Co. n 2864019) Formulations d'activateur de blanchiment
EP0482807A1 (fr) * 1990-10-23 1992-04-29 WARWICK INTERNATIONAL GROUP LIMITED (Co. n 2864019) Substrats actifs encapsulés libérables
WO1992012971A1 (fr) * 1991-01-18 1992-08-06 Basf Aktiengesellschaft Procede de production de 4h-3,1-benzoxazin-4-ones

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0456109A2 (fr) * 1990-05-10 1991-11-13 BASF Aktiengesellschaft Procédé pour préparer une composition granulaire d'activateur de blanchiment
EP0482806A1 (fr) * 1990-10-23 1992-04-29 WARWICK INTERNATIONAL GROUP LIMITED (Co. n 2864019) Formulations d'activateur de blanchiment
EP0482807A1 (fr) * 1990-10-23 1992-04-29 WARWICK INTERNATIONAL GROUP LIMITED (Co. n 2864019) Substrats actifs encapsulés libérables
WO1992012971A1 (fr) * 1991-01-18 1992-08-06 Basf Aktiengesellschaft Procede de production de 4h-3,1-benzoxazin-4-ones

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2022551583A (ja) * 2019-10-01 2022-12-12 モレキュラー スキン セラピューティクス，インコーポレイティド Ｋｌｋ５／７デュアル阻害剤としてのベンゾキサジノン化合物
US12281123B2 (en) 2019-10-01 2025-04-22 Molecular Skin Therapeutics, Inc. Benzoxazinone compounds as KLK5/7 dual inhibitors

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Publication number Publication date
AU2577192A (en) 1993-05-21
DE4134770A1 (de) 1993-04-29

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