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WO1993016161A1 - Composition granulaire d'activateurs de blanchiment a grains structures de maniere heterogene - Google Patents

Composition granulaire d'activateurs de blanchiment a grains structures de maniere heterogene Download PDF

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Publication number
WO1993016161A1
WO1993016161A1 PCT/EP1993/000181 EP9300181W WO9316161A1 WO 1993016161 A1 WO1993016161 A1 WO 1993016161A1 EP 9300181 W EP9300181 W EP 9300181W WO 9316161 A1 WO9316161 A1 WO 9316161A1
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WO
WIPO (PCT)
Prior art keywords
acid
bleach activator
activator composition
acids
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/EP1993/000181
Other languages
German (de)
English (en)
Inventor
Reinhard Mueller
Guenter Oetter
Alfred Oftring
Volker Schwendemann
Wolfgang Trieselt
Raimund Felder
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 WO1993016161A1 publication Critical patent/WO1993016161A1/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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
    • 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

  • Granular bleach activator composition from heterogeneously structured grains
  • the present invention relates to a new granular bleach activator composition composed of heterogeneously structured grains based on 4H-3, l-benzoxazin-4-one derivatives, optionally mixed with other 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-benzoxazine-4-one derivatives, have insufficient water solubility, especially in the temperature range between 25 and 60 ° C and are not sufficiently stable in the washing powder. It is therefore common practice to assemble these bleach activators to increase the dissolution rate and the effectiveness in the wash liquor and to improve the shelf life.
  • German patent application P 41 34 770.6 (1) describes a granular bleach activator composition composed of 4H-3, 1-benzoxazine-4-one derivatives, optionally mixed with other conventional bleach activators, and additives from the classes of substances anionic surfactants, nonionic Surfactants, zwitterionic surfactants, carboxyl-containing polymers, polysaccharides and polyalkylene glycols are described.
  • the bleach activators and the additives are distributed essentially homogeneously in this mixture.
  • WO 90/01535 (2) describes granular bleaching aids containing bleach activators from the class of the N-acyl and O-acyl compounds and water-soluble, film-forming polymers which serve as pelletizing aids; these bleaching aids additionally contain 2 to 15% by weight of a polyvalent carboxylic acid, hydroxycarboxylic acid or ether carboxylic acid with 3 to 6 C atoms in the molecule as stabilizer.
  • a homogeneous, dry premix is first used prepared which contains the bleach activator, the acid and part or all of the polymeric granulating aid. This mixture is sprayed with water or an aqueous solution of the remaining granulating aid and granulated.
  • 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 f denotes hydrogen, methyl, chlorine, nitro, acetoxy or hydroxy, or a mixture of the compounds I and other customary bleach activators
  • Dicarboxylic acids where the aforementioned carboxylic acids can additionally contain hydroxyl and amino groups in the molecule, and aliphatic C 3 - to C 7 -monohydroxycarboxylic acids
  • C 1 -C 4 -alkyl radicals for R are ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl and especially methyl.
  • Suitable Ci to C alkoxy groups for R are n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy and especially methoxy and ethoxy.
  • the aromatic radicals mentioned are preferred for R.
  • R ' which can be in the 5-, 6-, 7- or 8-position, denotes in particular 5- or 6-methyl, 6- or 7-chlorine and 7-nitro. R 'particularly preferably denotes hydrogen.
  • Coating is primarily understood to mean agglomerating coatings in which several primary grains are embedded in a bed of additives B.
  • the coating of the primary grains need not necessarily be complete. However, there may also be insulating sheaths of individual primary grains in the sense of a core-shell model.
  • Several enveloping layers can also be present, for example an additional surface coating (“coating") from component B via an agglomerate of several primary particles and additives B between and around these primary particles.
  • the additives B have above all a dispersing function, but can also have a protective function for the bleach activators against, for example, moisture, alkali or atmospheric oxygen in the form of surface coatings.
  • component A can contain, in addition to the compounds I, other conventional bleach activators.
  • the 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, N'-tetraacylated amines e.g. N, N, N ', N'-tetraacetyl-methylenediamine and -ethylenediamine, N, N-diacetylaniline, N, N-diacetyl- ⁇ -toluidine or 1,3-diacylated hydantoins such as 1,3-diacetyl-5,5- dimethylhydantoin;
  • acylated sugars for example pentaacetyl glucose.
  • bleach activators there are also additional bleach activators:
  • 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. 0-
  • N, N'-diacylsulfurylamides e.g. N, N'-dimethyl-N, N'-diacetyl-sulfurylamide or N, N'-diethyl-N, N'-dipropionyl-sulfurylamide;
  • Triacylcyanurates e.g. Triacetyl cyanurate or tribenzoyl cyanurate
  • Carboxylic anhydrides e.g. Benzoic anhydride, m-chloro-benzoic anhydride or phthalic anhydride;
  • 1,3-diacyl-4,5-diacyloxy imidazolines e.g. 1,3-di-acetyl-4,5-diacetoxyimidazoline;
  • diacylated 2,5-diketopiperazines e.g. 1,4-diacetyl-2,5-diketopiperazine;
  • ⁇ -acyloxy polyacyl malonamides e.g. ⁇ -acetoxy-N, N'-diacetylmalonamide
  • Diacyl-dioxohexahydro-1,3,5-triazines e.g. 1,5-Diacetyl-2,4-dioxohexahydro-1,3,5-triazine.
  • a preferred granular bleach activator composition consists
  • 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.
  • Alkyl benzenesulfonates in particular the alkali metal and ammonium salts of linear Cn ⁇ to Ci 3 alkylbenzenesulfonates, for example sodium dodecylbenzenesulfonate, are preferred.
  • the nonionic surfactants (2) used for B are, for example, primary or secondary alcohol oxalkylates such as fatty alcohol ethoxylates and alkylphenoloxyalkylates, fatty acid alkylol amides and especially alkyl glycosides, especially C ß to Cie monoalkyl glucosides, for example C ⁇ o monoalkyl glucoside.
  • primary or secondary alcohol oxalkylates such as fatty alcohol ethoxylates and alkylphenoloxyalkylates, fatty acid alkylol amides and especially alkyl glycosides, especially C ß to Cie monoalkyl glucosides, for example C ⁇ o monoalkyl glucoside.
  • Suitable zwitterionic surfactants (3) for B are, for example, secondary and tertiary amine oxides.
  • Suitable carboxyl group-containing polymers (4) for B are, above all, 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 ether. Of these, starch itself can best be used.
  • Particularly suitable polyalkylene glycols (6) for B are polyethylene glycols and ethylene oxide-propylene oxide copolymers.
  • the acidic alkali and alkaline earth metal salts of inorganic acids (7) for B are, above all, sodium hydrogen carbonate and sodium hydrogen sulfate, but also potassium hydrogen carbonate, potassium hydrogen sulfate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, disodium hydrogen phosphate, potassium or potassium hydrogen phosphate, calcium phosphate and phosphate.
  • aliphatic C ⁇ - to Cis-monocarboxylic acids aliphatic di- or tricarboxylic acids, aromatic mono- or dicarboxylic acids, where the aforementioned carboxylic acids can additionally contain hydroxyl and amino groups in the molecule
  • aliphatic C 3 - to C -monohydroxycarboxylic acids (8 eig ⁇ ) for B NEN for example, fatty acids such as lauric acid, myristic acid, palmitic acid and stearic acid, oxalic acid, malonic acid, Bern ⁇ acid, glutaric acid, adipic acid, pimelic acid, Korkkla- 're, nen yarn maleic acid, fumaric acid, tartaric acid, malic acid, citric acid, benzoic acid , Salicylic acid, anthranilic acid, sulfanilic acid, phthalic acid, ⁇ - and ß-naphthoic acid, naphthalic acid and lactic acid
  • palmitic acid palmitic acid
  • stearic acid oxalic acid
  • malonic acid succinic acid
  • glutaric acid adipic acid
  • pimelic acid tartaric acid
  • citric acid citric acid and benzoic acid
  • carboxylic acids mainly improve the color stability when stored in washing powders.
  • Mixtures of several additives B from one of groups (1) to (8) or from different groups can also be used.
  • the granular bleach activator compositions can also contain conventional auxiliaries C in the amounts customary for this in the coating.
  • auxiliaries e.g. as
  • Disintegrants, dispersants or finishing aids are used, for example polymers such as polyvinylpyrrolidone or inorganic salts such as sodium sulfate or sodium triphosphate.
  • the invention further relates to a process for the production of the granular bleach activator composition according to the invention, which is characterized in that grains are made from
  • anionic surfactants (2) nonionic surfactants,
  • component A (“primary granules”)
  • 4H-3, l-benzoxazin-4-one derivatives or mixtures thereof with other conventional bleach activators as solids in devices customary for this purpose, such as pin mills, jet mills, counter-jet mills or impact plate mills can be ground to the desired grain size.
  • the primary grains can also be produced by spraying the molten bleach activators A to the desired particle size, for example in a spray tower.
  • the granular bleach activator composition according to the invention is produced from components A and B by means of customary assembly methods and assemblies.
  • fine-grained bleach activator A and fine-grained additive B are mixed dry, the mixture is then agglomerated in water and then dried.
  • an aqueous solution of the additives B is sprayed onto fine-grained bleach activator A, then agglomerated and then dried.
  • a combination of the two preferred embodiments described can also be carried out.
  • the packing can be carried out dry by means of compaction on roller presses with subsequent shredding of the slugs to the desired agglomerate size.
  • coarse-grained bleach activator A and coarse-grained additive B can also be dry mixed, ground together to the desired grain size in one of the devices specified above, and then agglomerated in water.
  • All conventional mixing devices which ensure intensive mixing are suitable for dry mixing of components A and B, for example ploughshare mixers, Eirich intensive mixers or Ruberg twin-shaft intensive mixers.
  • the water content of the made-up composition is reduced to less than 5% by weight, preferably less than 2% by weight and in particular less than 0.5% by weight.
  • Drying takes place in suitable devices, for example fluidized bed, vacuum or tray dryers. Drying is preferably carried out at temperatures below 95 ° C.
  • the granular bleach activator composition according to the invention is additionally provided with a second coating (coating) from the additives B.
  • a second coating coating from the additives B.
  • the grains of the bleach activator composition according to the invention are coated with one or more additives B either by spraying an additive which melts at a low temperature or by spraying the aqueous solution of an additive over the grains. If necessary, the grains coated in this way must then be dried.
  • the grains of the bleach activator composition according to the invention should have an average diameter of about 0.1 to about 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 bleach activator in finely dispersed form.
  • the present invention furthermore relates to detergents 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 bleaches 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.
  • the usual constituents or compositions of detergents and cleaners 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 in the wash liquor very finely dispersed in a very short 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 fabric, irregular and spotty bleaching action, destruction of the textile fibers) do not occur.
  • the granular bleach activator composition according to the invention is sufficient in the washing powder, ie stable for several months; essentially no discoloration or decomposition processes can be observed.
  • 2-phenyl-4H-3, l-benzoxazin-4-one was ground in a pin mill to an average grain size of 20 ⁇ m.
  • the grain proportion greater than 80 ⁇ m was less than 5%.
  • 2-phenyl-4H-3, l-benzoxazin-4-one was ground in a pin mill to an average grain size of 20 ⁇ m.
  • the grain proportion greater than 80 ⁇ m was less than 5%.
  • 2-phenyl-4H-3, l-benzoxazin-4-one was ground in a pin mill to an average grain size of 20 ⁇ m.
  • the grain proportion greater than 80 ⁇ m was less than 5%.
  • 2-phenyl-4H-3, l-benzoxazin-4-one was ground in a pin mill to an average grain size of 20 ⁇ m.
  • the grain fraction larger than 80 ⁇ m was less than 5%.
  • 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: 12.5.
  • test fabric EMPA 115 Cotton fabric with immediate black as a test soil
  • the degree of bleaching was determined in each case on the basis of photometric measurement of the reflectance levels of the fabrics before and after washing in the Elrepho (Datacolor) from Zeiss at a wavelength of 460 nm (barium white standard according to DIN 5033).
  • the following relationship applies to the calculation of the bleaching degree BG (in%):
  • 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 45 ° C. after storing the detergent mixtures overnight, after 2 weeks and after 6 weeks.
  • detergent preparations which contained 4.0% by weight of the listed bleach activators of the prior art were prepared under the same conditions.

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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)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

Composition granulaire d'activateurs de blanchiment à grains structurés de manière hétérogène qui contiennent comme noyau: A) 30 à 98 % en poids, par rapport à l'ensemble de la composition granulaire d'activateurs de blanchiment, d'un ou plusieurs dérivés de 4H-3,1-benzoxazine-4-one de la formule générale (I), dans laquelle R représente alkyle C1 à C4, alcoxy C1 à C4, chlorométhyle, méthoxyméthyle, diméthylaminophényle, o-, m-, ou p-tolyl, p-chlorophényle, m-nitrophényle, m-méthoxyphényle ou m-méthylsulfonylphényl, R' désigne hydrogène, méthyle, chlore, nitro, acétoxy ou hydroxy, ou d'un mélange des composés de la formule (I) et d'autres activateurs de blanchiment habituels; et comme enrobage: B) 2 à 70 % en poids, par rapport à l'ensemble de la composition granulaire d'activateurs de blanchiment, d'un ou de plusieurs additif(s) des classes de substances suivantes: 1) tensioactifs anioniques, 2) tensioactifs non ioniques, 3) tensioactifs zwitterioniques, 4) polymérisats contenant des groupes carboxyliques, 5) polysaccharides, 6) polyalkylèneglycols, 7) sels de métaux alcalins et alcalino-terreux acides d'acides inorganiques, 8) acides monocarboxyliques C8 à C18 aliphatiques, acides di- et tricarboxyliques aliphatiques, acides mono- et dicarboxyliques aromatiques, les acides carboxyliques précités pouvant en outre contenir des groupes amino ou hydroxyl dans la molécule, et acides monohydroxycarboxyliques C3 à C7 aliphatiques.
PCT/EP1993/000181 1992-02-05 1993-01-27 Composition granulaire d'activateurs de blanchiment a grains structures de maniere heterogene Ceased WO1993016161A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19924203169 DE4203169A1 (de) 1992-02-05 1992-02-05 Koernige bleichaktivatorzusammensetzung aus heterogen aufgebauten koernern
DEP4203169.9 1992-02-05

Publications (1)

Publication Number Publication Date
WO1993016161A1 true WO1993016161A1 (fr) 1993-08-19

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AU (1) AU3451793A (fr)
DE (1) DE4203169A1 (fr)
WO (1) WO1993016161A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995004125A1 (fr) * 1993-07-31 1995-02-09 Henkel Kommanditgesellschaft Auf Aktien Agents de lavage a composants acides

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4483778A (en) * 1983-12-22 1984-11-20 The Procter & Gamble Company Peroxygen bleach activators and bleaching compositions
EP0332294A2 (fr) * 1988-02-11 1989-09-13 BP Chemicals Limited Activateurs de blanchiment dans des compositions détergentes
EP0332050A1 (fr) * 1988-03-10 1989-09-13 Henkel Kommanditgesellschaft auf Aktien Activateurs pour composés per minéraux
WO1990001535A1 (fr) * 1988-08-01 1990-02-22 Henkel Kommanditgesellschaft Auf Aktien Adjuvant de blanchiment granulaire renfermant des activateurs de blanchiment
EP0382464A2 (fr) * 1989-02-09 1990-08-16 Unilever Plc Procédé d'enrobage
EP0456109A2 (fr) * 1990-05-10 1991-11-13 BASF Aktiengesellschaft Procédé pour préparer une composition granulaire d'activateur de blanchiment
EP0482807A1 (fr) * 1990-10-23 1992-04-29 WARWICK INTERNATIONAL GROUP LIMITED (Co. n 2864019) Substrats actifs encapsulés libérables

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4483778A (en) * 1983-12-22 1984-11-20 The Procter & Gamble Company Peroxygen bleach activators and bleaching compositions
EP0332294A2 (fr) * 1988-02-11 1989-09-13 BP Chemicals Limited Activateurs de blanchiment dans des compositions détergentes
EP0332050A1 (fr) * 1988-03-10 1989-09-13 Henkel Kommanditgesellschaft auf Aktien Activateurs pour composés per minéraux
WO1990001535A1 (fr) * 1988-08-01 1990-02-22 Henkel Kommanditgesellschaft Auf Aktien Adjuvant de blanchiment granulaire renfermant des activateurs de blanchiment
EP0382464A2 (fr) * 1989-02-09 1990-08-16 Unilever Plc Procédé d'enrobage
EP0456109A2 (fr) * 1990-05-10 1991-11-13 BASF Aktiengesellschaft Procédé pour préparer une composition granulaire d'activateur de blanchiment
EP0482807A1 (fr) * 1990-10-23 1992-04-29 WARWICK INTERNATIONAL GROUP LIMITED (Co. n 2864019) Substrats actifs encapsulés libérables

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995004125A1 (fr) * 1993-07-31 1995-02-09 Henkel Kommanditgesellschaft Auf Aktien Agents de lavage a composants acides

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DE4203169A1 (de) 1993-08-12
AU3451793A (en) 1993-09-03

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