CA2041931A1 - Preparation of a particulate bleach activator composition - Google Patents
Preparation of a particulate bleach activator compositionInfo
- Publication number
- CA2041931A1 CA2041931A1 CA 2041931 CA2041931A CA2041931A1 CA 2041931 A1 CA2041931 A1 CA 2041931A1 CA 2041931 CA2041931 CA 2041931 CA 2041931 A CA2041931 A CA 2041931A CA 2041931 A1 CA2041931 A1 CA 2041931A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- pentaacetylglucose
- particulate
- bleach activator
- activator composition
- 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.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- 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
- C11D3/391—Oxygen-containing compounds
- C11D3/3912—Oxygen-containing compounds derived from saccharides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Detergent Compositions (AREA)
Abstract
O.Z. 0050/41600 Abstract of the Disclosure: A particulate bleach activa-tor composition containing A) from 40 to 95% by weight of pentaacetylglucose or a mixture of pentaacetylglucose and further customary bleach activators and B) from 5 to 60% by weight of one or more additives selected from the following classes:
(1) basic inorganic alkali metal and alkaline earth metal salts, (2) mono-, di- and trialkylamines, (3) chelating organic complexing agents combined with hydroxycarboxylic acids, (4) water-insoluble inorganic silicates, (5) anionic surfactants, (6) nonionic surfactants, (7) carboxyl-containing polymers and (8) polysaccharides, is produced by (a) reacting glucose with acetic anhydride to give pentaacetylglucose, (b) removing the resulting acetic acid by distillation down to a residual level of from 0.2 to 10% by weight, (c) admixing the reaction mixture with one or more additives B and optionally further customary bleach activators, and (d) converting the product into a particulate form by a size-enlargement process.
(1) basic inorganic alkali metal and alkaline earth metal salts, (2) mono-, di- and trialkylamines, (3) chelating organic complexing agents combined with hydroxycarboxylic acids, (4) water-insoluble inorganic silicates, (5) anionic surfactants, (6) nonionic surfactants, (7) carboxyl-containing polymers and (8) polysaccharides, is produced by (a) reacting glucose with acetic anhydride to give pentaacetylglucose, (b) removing the resulting acetic acid by distillation down to a residual level of from 0.2 to 10% by weight, (c) admixing the reaction mixture with one or more additives B and optionally further customary bleach activators, and (d) converting the product into a particulate form by a size-enlargement process.
Description
2 ~ 3 ~ ~
O.Z. 0050/41600 Preparation of a particulate bleach activator composition The present invention relates to an improved process for preparing a particulate bleach activator composition containing A) from 40 to 95% by weight of pentaacetylglucose or a .~ mixture of pentaacetylglucose and further customary bleach activators and . ~) from 5 to 60~ by weight of one or more additives selected from the following classes:
: 10 (1) basic inorganic alkali metal and alkaline earth metal salts, . (2) mono-, di- and trialkylamines, (3) chelating organic complexing agents combined with hydroxycarboxylic acids, : 15 ~4) water-insoluble inorganic silicates, (5) anionic surfactants, (6) nonionic surfactants, (7) carboxyl-containing pol~mers and (B) polysaccharides.
Some of the particulate bleach activator composi-~ions are novel products. The present invention ~herefore - also relates to these novel products.
The pre~ent invention further relates to deter-gents which contain the bleach ac~ivator composition of - 25 components A and B (1) to (8).
EP-B-240 057 (1) relates to a particulate, phosphorus-free bleach activator composition comprising a finely divided bleach activator, an inert, non-alka-:- line, water-soluble inorganic or organic salt, a water-soluble, film-forming polymeric material and a clay material.
EP-A-156 977 (2) relates to a process for prepar-ing a granul2ted bleach activator from an active acety-lated compound, for example pentaacetylglucose, and 3S sodium tripolyphosphate, wherein the active compound, which has a moisture content of from ~0 to 65% by weight, is mixed with sodium tripolyphosphate, then granulated ,: .
3 ~
- 2 - O.Z. 0050/41600 and finally dried~
EP-B-02~ 432 (3) describes a detergent constitu-ent comprising a particulate mixture in the form of granules of an organic peroxyacid bleach precursor, for example glucose pentaacetate, with silica or a water-insoluble silicate and an alkoxylated nonionic surface-active agent.
US-A-483 778 (4) relates to a particulate pero~y bleach activator composition containing a binder or coating material comprising nonionic surfactants, poly-ethylene glycol~, fatty acids, anionic surfactants or film-forming polymers such as homo- and copolymers of acrylic acid, hydroxyacrylic acid, methacrylic acid or cellulose derivatives thereof.
15~he customary way of incorporating additives into the b].each activator substance, described for example in (2), first requires the removal of the acetic acid formed from the acetic anhydride which is usually used for the acetylation, for example by precipitating the acetylated product with water or a water-alcohol mixture, filtering it off and if necessary drying it. However, this is a complicated and uneconomical operation, in particular on ; an industrial scale. The crystallization directly from the reaction mixture, which must precede any size-enlargement process, is generally unsuccessful due to the presence of small amounts of acetic acid which are Lmpo~sible to remove by distillation and of further by-products.
It is an object of the present inven~ion to provide a ready-made bleach activa~or composition obtain-able directly from the acetic acid-containing crude product of the acetylation stage.
We have found that this ob~ect is achie~ed by a process for preparing the particulate bleach activator composition defined at the beginning, comprising the steps of (a) reacting glucose wi~h acetic anhydride to give pentaacetylylucoqe, .' .
....
.
2 ~ 3 ~
~ 3 ~ -Z- 0o5o/4l6oo (b) removing the resulting acetic acid by distillation down to a residual level of from 0.2 to 10~ by weight, (c) admixing the reaction mixture with one or mor~
additives B and optionally further customary bleach - activators, and (d) converting the product into a particulate form by a size-enlargement process.
~he reaction of glucose as per (a) with an appropriate amount of acetic anhydride to gi~e crude pentaacetylglucose is carried out in a conventional manner.
The distillation (b) to remove acetic acid i advan~a~eously carried out under mild conditions a~ a reduced pressure of from about 10 to about 200 mbar in order not to expose the acetylated glucose to any decom-position proce~s. It is very difficult to reduce the :~ residual level of acetic acid to below 0O5~ in particular 0.2/ % by weight. However, for the rest of the process of the present invention a residual acetic acid content of up to 10 t in particular 5, % by weight is still toler-able.
The acetic acid- and byproduct~cont~ining reaction mixture is admixed as per (c) with the additives B and optionally further customary bleach activators. It i5 advantageou~ here, on account of the be~ter mixing, i~
th~ reaction mixture is still in a liquid or at least pla~tically deformable state. The addition of these substance~ may take place in stirred or kneaded appara-tus. Preference, howe~er, is given to using one or more cu~tomary extruders, ~ince they provide the most rapid and efficient mi~ing and, what is more, may be followed ` directly by the conversion step (d~. Beside~ ex~rusion, however, it is also possible to use other conversion methods such as ~pray crystalllzation or pressure compac-tion. The extruders may also first be followed by cooling and size-reduction mean~.
2~ 3~
_ 4 _ O.Z. 0050~41600 Particular preference is given to using corotat-ing continuous twin-screw extruders for incorporating the additives B and any further cus~omary bleach activators.
They advantageously have a self-cleaninq profile. The product, crystallized via dies to a certain viscosity, is advantageously molded into continuous threa~6 which, having cooled on a moving belt, are comminuted. The cooling of the still warm liquid crude produc~ from (b) in the extruder is preferably effected with water at from 30 to 70C in order that the viscosity of the melt should not be too high, and ~hus makes it possible to achieve efficient dispersion of the additives B and any further customa~y bleach activators after they have been mixed in. On the other hand, the cooling must be adequate to produce a sufficient number of cryætallization nuclei and to obtain the minimum viscosity required for extruding dimensionally stable filaments in the first place.
The particles o the composition range in size from about 0.5 to about 3 mm. Depending on the size-enlargement method employed, the particles may be in the form of prills, granules, pellets or compacts. In general the particles are white or creamy in color and dissolve readily in lukewarm water within a short period.
To improve the bleach activator effect, component A may contain further customary bleach activators as well as pentaacetylglucose. The weight ratio of the additional bleach activators to ~he pentaacetylglucose in this case ; will normally be from 1:99 to 90:10, preferably from l:99 to 50:50-Possible additional bleach activators are in particular:
., - acyloxybenzenesulfonic acids and their alkali me~al and alkaline earth metal alts, eg. sodium p-isonon-anoyloxybenzenesulfonate or sodium p-benzoyloxy-: 35 benzenesulfonate;
- ~-diacylated and N,~'-tetraacylated amines, eg.
N,N,N',N'-tetraacetyl-methylenediamine and . .
~, . . .
.
, . ~
- 5 - O.Z. 0050/41600 -ethylenediamine,N,N-diacetylaniline,N,N-diacetyl-p~toluidine or 1,3-diacylated hydantoins such as 1,3-diacetyl-5,5-dLmethylhydantoin;
- 4H-benz-1,3-oxazin-4-ones,eg.2-phenyl-4H~benz-1,3-S oxazin~4-one or 2-methyl-4~-benz-1,3-oxazin-4-one.
But it is also possible to use the following as additional bleach activators:
- N-alkyl-N-sulfonylcarboxamides, eg. ~-methyl-N-mesylacetamide or N-methyl-N-mesylbenzamide;
- N-acylated cyclic hydrazide~, acylated triazole~ or urazoles, eg. monoacetyl maleohydrazide;
- O,N,N-trisubstituted hydroxylamines~ eg. O-benzoyl-N,N-succinylhydroxylamine, O-acetyl-~,N-succinyl-hydroxylamine or O,N,N-triacetylhydroxylamine;
- N,~'-diacylsulfurylamides, eg. N,N'-dLmethyl-N,N'-diacetylsulfurylamideorN,N'-diethyl-N,N'-dipropio-nylsulfurylamide;
- triacyl cyanurates, eg. triacetyl cyanurate or tribenzoyl cyanurate;
- carboxylic anhydrides, eg. benzoic anhydride, m-chlorobenzoic anhydride or phthalic anhydride;
- 1,3-diacyl-4,5-diacyloxyimidazolines, eg. 1,3-diacetyl-4,5-diacetoxyimidazoline;
tetraace~ylglycoluril and tetrapropionylglycoluril;
- diacylated 2,5-diketopiperazines, eg. 1,4~diacetyl~
; 2,5-dLketopiperazine;
~ acylation product~ of propylenediurea and 2,2-dLme~hylpropylenediurea,eg.tetraacetylpropylenedi-urea;
- ~-acyloxypolyacylmalonamides, eg. ~-acetoxy-N,N'-diacetylmalonamide;
- diacyldioxohe~ahydro-1,3,5-triazine~, eg. 1,5-diacetyl-2,4-dioxohexahydro-1,3,5-tria~ine.
A preferred particulate bleach activator composi-tion consi~ts of A) from 45 to 85% by weight of pentaacetylglucose or amixture of pentaacetylgluco~e and further cu~tomary - 6 - O.Z. 0050/41600 bleach activators, B) from 10 to 50% by weight of one or more additives B, and C) from 0.3 to 20% by weight of ssistants customary here and o~ by-products from the preparation of the composition.
The basic inorganic alkali metal and alkaline earth metal salts ~1) used are in particular hydroxides such as sodium hydroxide, potassium hydroxide, magnesium hydroxide and calcium hydroxide, carbonates such as sodium car~onate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, magnesium carbonate, magnesium hydroxide bicarbonate and calcium carbonate and other basic alkali metal and alkaline earth metal salts of weak acids such as water-soluble sodium silicate.
The mono-, di- and trial~Aylamines (2) used are most advantageously those having at least one relatively long alkyl group of about 8 - 25 carbon atoms. Examples thereof are N-dodecylamine, N-methyl-N-dodecylamine, N,N-dimethyl-N-dodecylamine, N,N-dimethyl-N-myristylamine, N,N-dimethyl-N-ce~ylamin~ and N,N-dimethyl-N-stearyl-amine.
; The chelating organic complexing agents (3), which are used with hydroxycarboxylic acid~ such as citric acid, are in particular nitrilotriacetic acid, ethylenediaminetetraacetic acid, isoserinediacetic acid and organic pho~phonic acid~ such as nitrilotrLmethylene-phosphonic acid, ethylenediaminetetramethylenephosphonic acid and hydroxyethanediphosphonic acid and also the ~; 30 corre~ponding alkali metal salts.
`~ The water-insoluble inorganic silicates (4) can `~- be alkali metal and alkaline earth metal alumosilica~es such as zeolites, for e~ample zeolite A, aluminum magnesium ~ilicates (bleaching earths) such as bentonite 3S or attapulgite and magnesium silicates such as serpentine or talc.
Suitable anionic surfactants (5) are for example . .
~' .. . .
:
3 ~
- 7 - O.Z. 0050/41600 alkali metal salts of fatty acids, alkylbenzenesulfon-ates, alkanesulfonates, ~-olefinsulfonates, hydroxy-alkanesulfonates, ~-sulfo fatty acid esters, alkyl-sulfates, alkyl ether sulfates and fatty alcohol ether sulfates.
The nonionic surfactants (6) used are for example primary or secondary alcohol alkoxylates such as fatty alcohol ethoxylates and also alkylphenol alkoxylates, fatty acid alkylolamides and amine oxides.
- 10 The carboxyl-containing polymers (7) are in particular homopolymers of acrylic acid or methacrylic acid and also copolymers o~ acrylic and/or methacrylic acid, eg. acrylic acid/maleic acid copolymers, and the corresponding alkali metal or ammonium salts.
The polysaccharides (8) are most advantageously starch, a~ylo~e and derivatives of these naturally occurring polysaccharides such as carbox~methylcellulose or sulfated cellulose sthers.
The preferred component B i~ an alkali metal salt of a fatty acid or a mixture of such salt~ or a mixture of such a salt with other additives B such as water-insoluble inorganic silicates~ carboxyl-containing polymer~ or polysaccharides. Fatty acids for the purposes of the present invention are ~aturated or unsaturated aliphatic monocarboxylic acids of from abou~ 6 to about 20, in particular from 12 to 18, carbon atoms.
Examples o~ such fatty acid salts are sodium stearate, po~assium stearate, sodium palmitate, potassium palmitate, sodium myristate, potassium myrista~e, sodium laurate~ potassium laurate, sodium oleate, potassium oleate, sodium linoleate and potassium linoleate.
Usually, these fatty acid salt~ are used as mixtures in the form of soaps. Customary technical grade soaps are ; for example coco fat soaps and tallow fat soap.
The particulate bleach activator compositions may additionally contain customary assistants in their cus~omary amounts. Customary assistan~s, which may serve ;
9 ~ ~
- 8 - O.Z. 0050/41600 for example as disintegra~ors, dispersants or size-enlargement aids, are for example inorganic salts such as sodium sulfate or sodium triphospha~e.
Byproducts from the preparation of the composi~
tion include, inter alia, acetic acid salts, for example alkali metal acetate such as sodium acetate and potassium acetate. Additionally, still unacetylated glucose, incompletely acetylated glucose and other glucose by-products may be pre~ent in the bleach activator composi-tion. The~e byproducts may account for up to about 10%
by weight, in the least fa~orable cases up to about 15%
by weight. They do not impair the bleach activator effect or the detergency.
The present invention also provides novel parti-culate bleach activator compositions containing A) from 40 to 95% by weight of pentaacetylglucose or a mixture of pentaacetylglucose and further customary bleach activators, and B) from 5 to 60~ by weight of one or more additives selected from the following classes:
(1) basic inorganic alkali metal and alkaline earth metal salts, (2) mono-, di- and trialkylamines, (3) chelating organic complexing agents combined with hydroxycarboxylic acids.
The present inventlon further provides de~ergen~s which contain from 0.5 to 20% by weight, preferably ~rom 1 to 10% by weight, of the particulate bleach activator composition and the customary bleaching agents in the customary amount~. These detergent~ are in particular textile detergent~ in powder form (washing powders) into which the compo~itions of the present invention are incorporated during or after manufacture. Customary cons~ituents and compositions of de~ergents are known to those skilled in the art and therefore need not be discussed here in greater detail.
The reason why the particulate bleach activator .~, .
; .
3 ~
- 9 - O.Z. 0050/41600 compositions described are so easy to produce is that the addition o the additives B to the acetic acid- and by-product-containing crude product from the acetyLation of glucose unexpectedly brings about a rapid solidification and crystallization, giving a product ~ithout tackiness, which makes the size-enlargement process possible i~ the first place. If no B is added, substantially no rapid and reproducible crystallization takes place.
The addition of B also causes the complete binding of the troublesome acetic acid odor, facilitates the mixability and in particular the extrudability of the product, and increaseq the shelf life of the bleach activator composition of the present invention in alka-line detergents compared with ready-made bleach activator compositions of the prior art.
0.3 g of 96% strength by weight sulfuric acid were added at room temperature with s~irring to 561 g (5.5 mol) of acetic anhydride (91% by weight purity).
Then 180 g (1.0 mol) of anhydrous glucose were added to the 60C mixture a little at a time while the temperature was maintained at 60 - 70C. The mixture was subsequently stirred at 60C for 2 hours, the sulfuric acid was neutralized with 0.5 g of 50% streng~h by weight aqueous sodium hydroxide solution, and the acetic acid formed was distilled off at 20 mbar down to a residual level of 4%
by weight. Thi~ left about 400 ~ of crude product.
The still warm liquid crude product was admixed with the additives and auxiliarie~ ted below in the Table of the prepared bleach activator compositions in a corotating twin screw extruder of the ~DS W series from Werner h Pfleiderer. The temperature of the housing and the screws for this mixing process was adjusted with cooling to about 50C and the pressurQ in the extruder was no~ more than 20 bar. The average residence time in ; the extruder was abou~ l min. The extruded threads were from 1.5 to 2 mm in diameter. Their temperature on exit ~s~9311 - 10 - O.Z. 0050/41600 from the dies was 60-70C. They were cooled to room temperature on a moving belt and comminuted to granules having a length-to-diameter ratio of from 1:1 to 3;1.
On storage in customary alkaline washing powders at 38C and 76% atmospheric humidity the activity of the particulate bleach activator composition obtained was found to be still at almost its original level several weeks later.
, .
., i.~
,,~
':
r ;
'~-3 ~
O . Z . 0050/~1600 _~ ~
O I I N I I I I O I L~ 1~ o U~
1~ t~
~D O I I r~
U~
o ~1 " o ~ ~r~ I o I I I I I I I
,-', X Co _l '` $ E~
~ . I~
., O ~ ~ C~l I I I I I I I I~ ~ I o ~!:
. _~
- ~
., 01 ~r `.:P
,~ ~
dP
_. ~ o O O
_I ~ O O U~
O O 1~ 0 ~P
~ ~ o ~ ~
~1~ o 'a ~ h u~ 1~ 1 ~ S ~ a~
o o r~
O
O n~ C h Iq ~1 3 O ~ h 1~ -i O t~
O O
o u a~ o _~
:1 ~ o -I ~3 3 :~ U ~ U a~
_I ~ o ~ a) ~1 ~ ~ ~ o P ~ ~ u ~ ~ a~
U O S ~
U ~ ~ ~ (~ 0 ~ I h ,~ t U E~ a) u t) O ~ 1 to ~ h ~1 0 0 :1 o h ~ O --I ~ O ~:: h h ~
_l o a~ o o o o o P O ~ o ~ o ~ o o m u P1 u~ c~ u t¢ tn ~ u c~
O.Z. 0050/41600 Preparation of a particulate bleach activator composition The present invention relates to an improved process for preparing a particulate bleach activator composition containing A) from 40 to 95% by weight of pentaacetylglucose or a .~ mixture of pentaacetylglucose and further customary bleach activators and . ~) from 5 to 60~ by weight of one or more additives selected from the following classes:
: 10 (1) basic inorganic alkali metal and alkaline earth metal salts, . (2) mono-, di- and trialkylamines, (3) chelating organic complexing agents combined with hydroxycarboxylic acids, : 15 ~4) water-insoluble inorganic silicates, (5) anionic surfactants, (6) nonionic surfactants, (7) carboxyl-containing pol~mers and (B) polysaccharides.
Some of the particulate bleach activator composi-~ions are novel products. The present invention ~herefore - also relates to these novel products.
The pre~ent invention further relates to deter-gents which contain the bleach ac~ivator composition of - 25 components A and B (1) to (8).
EP-B-240 057 (1) relates to a particulate, phosphorus-free bleach activator composition comprising a finely divided bleach activator, an inert, non-alka-:- line, water-soluble inorganic or organic salt, a water-soluble, film-forming polymeric material and a clay material.
EP-A-156 977 (2) relates to a process for prepar-ing a granul2ted bleach activator from an active acety-lated compound, for example pentaacetylglucose, and 3S sodium tripolyphosphate, wherein the active compound, which has a moisture content of from ~0 to 65% by weight, is mixed with sodium tripolyphosphate, then granulated ,: .
3 ~
- 2 - O.Z. 0050/41600 and finally dried~
EP-B-02~ 432 (3) describes a detergent constitu-ent comprising a particulate mixture in the form of granules of an organic peroxyacid bleach precursor, for example glucose pentaacetate, with silica or a water-insoluble silicate and an alkoxylated nonionic surface-active agent.
US-A-483 778 (4) relates to a particulate pero~y bleach activator composition containing a binder or coating material comprising nonionic surfactants, poly-ethylene glycol~, fatty acids, anionic surfactants or film-forming polymers such as homo- and copolymers of acrylic acid, hydroxyacrylic acid, methacrylic acid or cellulose derivatives thereof.
15~he customary way of incorporating additives into the b].each activator substance, described for example in (2), first requires the removal of the acetic acid formed from the acetic anhydride which is usually used for the acetylation, for example by precipitating the acetylated product with water or a water-alcohol mixture, filtering it off and if necessary drying it. However, this is a complicated and uneconomical operation, in particular on ; an industrial scale. The crystallization directly from the reaction mixture, which must precede any size-enlargement process, is generally unsuccessful due to the presence of small amounts of acetic acid which are Lmpo~sible to remove by distillation and of further by-products.
It is an object of the present inven~ion to provide a ready-made bleach activa~or composition obtain-able directly from the acetic acid-containing crude product of the acetylation stage.
We have found that this ob~ect is achie~ed by a process for preparing the particulate bleach activator composition defined at the beginning, comprising the steps of (a) reacting glucose wi~h acetic anhydride to give pentaacetylylucoqe, .' .
....
.
2 ~ 3 ~
~ 3 ~ -Z- 0o5o/4l6oo (b) removing the resulting acetic acid by distillation down to a residual level of from 0.2 to 10~ by weight, (c) admixing the reaction mixture with one or mor~
additives B and optionally further customary bleach - activators, and (d) converting the product into a particulate form by a size-enlargement process.
~he reaction of glucose as per (a) with an appropriate amount of acetic anhydride to gi~e crude pentaacetylglucose is carried out in a conventional manner.
The distillation (b) to remove acetic acid i advan~a~eously carried out under mild conditions a~ a reduced pressure of from about 10 to about 200 mbar in order not to expose the acetylated glucose to any decom-position proce~s. It is very difficult to reduce the :~ residual level of acetic acid to below 0O5~ in particular 0.2/ % by weight. However, for the rest of the process of the present invention a residual acetic acid content of up to 10 t in particular 5, % by weight is still toler-able.
The acetic acid- and byproduct~cont~ining reaction mixture is admixed as per (c) with the additives B and optionally further customary bleach activators. It i5 advantageou~ here, on account of the be~ter mixing, i~
th~ reaction mixture is still in a liquid or at least pla~tically deformable state. The addition of these substance~ may take place in stirred or kneaded appara-tus. Preference, howe~er, is given to using one or more cu~tomary extruders, ~ince they provide the most rapid and efficient mi~ing and, what is more, may be followed ` directly by the conversion step (d~. Beside~ ex~rusion, however, it is also possible to use other conversion methods such as ~pray crystalllzation or pressure compac-tion. The extruders may also first be followed by cooling and size-reduction mean~.
2~ 3~
_ 4 _ O.Z. 0050~41600 Particular preference is given to using corotat-ing continuous twin-screw extruders for incorporating the additives B and any further cus~omary bleach activators.
They advantageously have a self-cleaninq profile. The product, crystallized via dies to a certain viscosity, is advantageously molded into continuous threa~6 which, having cooled on a moving belt, are comminuted. The cooling of the still warm liquid crude produc~ from (b) in the extruder is preferably effected with water at from 30 to 70C in order that the viscosity of the melt should not be too high, and ~hus makes it possible to achieve efficient dispersion of the additives B and any further customa~y bleach activators after they have been mixed in. On the other hand, the cooling must be adequate to produce a sufficient number of cryætallization nuclei and to obtain the minimum viscosity required for extruding dimensionally stable filaments in the first place.
The particles o the composition range in size from about 0.5 to about 3 mm. Depending on the size-enlargement method employed, the particles may be in the form of prills, granules, pellets or compacts. In general the particles are white or creamy in color and dissolve readily in lukewarm water within a short period.
To improve the bleach activator effect, component A may contain further customary bleach activators as well as pentaacetylglucose. The weight ratio of the additional bleach activators to ~he pentaacetylglucose in this case ; will normally be from 1:99 to 90:10, preferably from l:99 to 50:50-Possible additional bleach activators are in particular:
., - acyloxybenzenesulfonic acids and their alkali me~al and alkaline earth metal alts, eg. sodium p-isonon-anoyloxybenzenesulfonate or sodium p-benzoyloxy-: 35 benzenesulfonate;
- ~-diacylated and N,~'-tetraacylated amines, eg.
N,N,N',N'-tetraacetyl-methylenediamine and . .
~, . . .
.
, . ~
- 5 - O.Z. 0050/41600 -ethylenediamine,N,N-diacetylaniline,N,N-diacetyl-p~toluidine or 1,3-diacylated hydantoins such as 1,3-diacetyl-5,5-dLmethylhydantoin;
- 4H-benz-1,3-oxazin-4-ones,eg.2-phenyl-4H~benz-1,3-S oxazin~4-one or 2-methyl-4~-benz-1,3-oxazin-4-one.
But it is also possible to use the following as additional bleach activators:
- N-alkyl-N-sulfonylcarboxamides, eg. ~-methyl-N-mesylacetamide or N-methyl-N-mesylbenzamide;
- N-acylated cyclic hydrazide~, acylated triazole~ or urazoles, eg. monoacetyl maleohydrazide;
- O,N,N-trisubstituted hydroxylamines~ eg. O-benzoyl-N,N-succinylhydroxylamine, O-acetyl-~,N-succinyl-hydroxylamine or O,N,N-triacetylhydroxylamine;
- N,~'-diacylsulfurylamides, eg. N,N'-dLmethyl-N,N'-diacetylsulfurylamideorN,N'-diethyl-N,N'-dipropio-nylsulfurylamide;
- triacyl cyanurates, eg. triacetyl cyanurate or tribenzoyl cyanurate;
- carboxylic anhydrides, eg. benzoic anhydride, m-chlorobenzoic anhydride or phthalic anhydride;
- 1,3-diacyl-4,5-diacyloxyimidazolines, eg. 1,3-diacetyl-4,5-diacetoxyimidazoline;
tetraace~ylglycoluril and tetrapropionylglycoluril;
- diacylated 2,5-diketopiperazines, eg. 1,4~diacetyl~
; 2,5-dLketopiperazine;
~ acylation product~ of propylenediurea and 2,2-dLme~hylpropylenediurea,eg.tetraacetylpropylenedi-urea;
- ~-acyloxypolyacylmalonamides, eg. ~-acetoxy-N,N'-diacetylmalonamide;
- diacyldioxohe~ahydro-1,3,5-triazine~, eg. 1,5-diacetyl-2,4-dioxohexahydro-1,3,5-tria~ine.
A preferred particulate bleach activator composi-tion consi~ts of A) from 45 to 85% by weight of pentaacetylglucose or amixture of pentaacetylgluco~e and further cu~tomary - 6 - O.Z. 0050/41600 bleach activators, B) from 10 to 50% by weight of one or more additives B, and C) from 0.3 to 20% by weight of ssistants customary here and o~ by-products from the preparation of the composition.
The basic inorganic alkali metal and alkaline earth metal salts ~1) used are in particular hydroxides such as sodium hydroxide, potassium hydroxide, magnesium hydroxide and calcium hydroxide, carbonates such as sodium car~onate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, magnesium carbonate, magnesium hydroxide bicarbonate and calcium carbonate and other basic alkali metal and alkaline earth metal salts of weak acids such as water-soluble sodium silicate.
The mono-, di- and trial~Aylamines (2) used are most advantageously those having at least one relatively long alkyl group of about 8 - 25 carbon atoms. Examples thereof are N-dodecylamine, N-methyl-N-dodecylamine, N,N-dimethyl-N-dodecylamine, N,N-dimethyl-N-myristylamine, N,N-dimethyl-N-ce~ylamin~ and N,N-dimethyl-N-stearyl-amine.
; The chelating organic complexing agents (3), which are used with hydroxycarboxylic acid~ such as citric acid, are in particular nitrilotriacetic acid, ethylenediaminetetraacetic acid, isoserinediacetic acid and organic pho~phonic acid~ such as nitrilotrLmethylene-phosphonic acid, ethylenediaminetetramethylenephosphonic acid and hydroxyethanediphosphonic acid and also the ~; 30 corre~ponding alkali metal salts.
`~ The water-insoluble inorganic silicates (4) can `~- be alkali metal and alkaline earth metal alumosilica~es such as zeolites, for e~ample zeolite A, aluminum magnesium ~ilicates (bleaching earths) such as bentonite 3S or attapulgite and magnesium silicates such as serpentine or talc.
Suitable anionic surfactants (5) are for example . .
~' .. . .
:
3 ~
- 7 - O.Z. 0050/41600 alkali metal salts of fatty acids, alkylbenzenesulfon-ates, alkanesulfonates, ~-olefinsulfonates, hydroxy-alkanesulfonates, ~-sulfo fatty acid esters, alkyl-sulfates, alkyl ether sulfates and fatty alcohol ether sulfates.
The nonionic surfactants (6) used are for example primary or secondary alcohol alkoxylates such as fatty alcohol ethoxylates and also alkylphenol alkoxylates, fatty acid alkylolamides and amine oxides.
- 10 The carboxyl-containing polymers (7) are in particular homopolymers of acrylic acid or methacrylic acid and also copolymers o~ acrylic and/or methacrylic acid, eg. acrylic acid/maleic acid copolymers, and the corresponding alkali metal or ammonium salts.
The polysaccharides (8) are most advantageously starch, a~ylo~e and derivatives of these naturally occurring polysaccharides such as carbox~methylcellulose or sulfated cellulose sthers.
The preferred component B i~ an alkali metal salt of a fatty acid or a mixture of such salt~ or a mixture of such a salt with other additives B such as water-insoluble inorganic silicates~ carboxyl-containing polymer~ or polysaccharides. Fatty acids for the purposes of the present invention are ~aturated or unsaturated aliphatic monocarboxylic acids of from abou~ 6 to about 20, in particular from 12 to 18, carbon atoms.
Examples o~ such fatty acid salts are sodium stearate, po~assium stearate, sodium palmitate, potassium palmitate, sodium myristate, potassium myrista~e, sodium laurate~ potassium laurate, sodium oleate, potassium oleate, sodium linoleate and potassium linoleate.
Usually, these fatty acid salt~ are used as mixtures in the form of soaps. Customary technical grade soaps are ; for example coco fat soaps and tallow fat soap.
The particulate bleach activator compositions may additionally contain customary assistants in their cus~omary amounts. Customary assistan~s, which may serve ;
9 ~ ~
- 8 - O.Z. 0050/41600 for example as disintegra~ors, dispersants or size-enlargement aids, are for example inorganic salts such as sodium sulfate or sodium triphospha~e.
Byproducts from the preparation of the composi~
tion include, inter alia, acetic acid salts, for example alkali metal acetate such as sodium acetate and potassium acetate. Additionally, still unacetylated glucose, incompletely acetylated glucose and other glucose by-products may be pre~ent in the bleach activator composi-tion. The~e byproducts may account for up to about 10%
by weight, in the least fa~orable cases up to about 15%
by weight. They do not impair the bleach activator effect or the detergency.
The present invention also provides novel parti-culate bleach activator compositions containing A) from 40 to 95% by weight of pentaacetylglucose or a mixture of pentaacetylglucose and further customary bleach activators, and B) from 5 to 60~ by weight of one or more additives selected from the following classes:
(1) basic inorganic alkali metal and alkaline earth metal salts, (2) mono-, di- and trialkylamines, (3) chelating organic complexing agents combined with hydroxycarboxylic acids.
The present inventlon further provides de~ergen~s which contain from 0.5 to 20% by weight, preferably ~rom 1 to 10% by weight, of the particulate bleach activator composition and the customary bleaching agents in the customary amount~. These detergent~ are in particular textile detergent~ in powder form (washing powders) into which the compo~itions of the present invention are incorporated during or after manufacture. Customary cons~ituents and compositions of de~ergents are known to those skilled in the art and therefore need not be discussed here in greater detail.
The reason why the particulate bleach activator .~, .
; .
3 ~
- 9 - O.Z. 0050/41600 compositions described are so easy to produce is that the addition o the additives B to the acetic acid- and by-product-containing crude product from the acetyLation of glucose unexpectedly brings about a rapid solidification and crystallization, giving a product ~ithout tackiness, which makes the size-enlargement process possible i~ the first place. If no B is added, substantially no rapid and reproducible crystallization takes place.
The addition of B also causes the complete binding of the troublesome acetic acid odor, facilitates the mixability and in particular the extrudability of the product, and increaseq the shelf life of the bleach activator composition of the present invention in alka-line detergents compared with ready-made bleach activator compositions of the prior art.
0.3 g of 96% strength by weight sulfuric acid were added at room temperature with s~irring to 561 g (5.5 mol) of acetic anhydride (91% by weight purity).
Then 180 g (1.0 mol) of anhydrous glucose were added to the 60C mixture a little at a time while the temperature was maintained at 60 - 70C. The mixture was subsequently stirred at 60C for 2 hours, the sulfuric acid was neutralized with 0.5 g of 50% streng~h by weight aqueous sodium hydroxide solution, and the acetic acid formed was distilled off at 20 mbar down to a residual level of 4%
by weight. Thi~ left about 400 ~ of crude product.
The still warm liquid crude product was admixed with the additives and auxiliarie~ ted below in the Table of the prepared bleach activator compositions in a corotating twin screw extruder of the ~DS W series from Werner h Pfleiderer. The temperature of the housing and the screws for this mixing process was adjusted with cooling to about 50C and the pressurQ in the extruder was no~ more than 20 bar. The average residence time in ; the extruder was abou~ l min. The extruded threads were from 1.5 to 2 mm in diameter. Their temperature on exit ~s~9311 - 10 - O.Z. 0050/41600 from the dies was 60-70C. They were cooled to room temperature on a moving belt and comminuted to granules having a length-to-diameter ratio of from 1:1 to 3;1.
On storage in customary alkaline washing powders at 38C and 76% atmospheric humidity the activity of the particulate bleach activator composition obtained was found to be still at almost its original level several weeks later.
, .
., i.~
,,~
':
r ;
'~-3 ~
O . Z . 0050/~1600 _~ ~
O I I N I I I I O I L~ 1~ o U~
1~ t~
~D O I I r~
U~
o ~1 " o ~ ~r~ I o I I I I I I I
,-', X Co _l '` $ E~
~ . I~
., O ~ ~ C~l I I I I I I I I~ ~ I o ~!:
. _~
- ~
., 01 ~r `.:P
,~ ~
dP
_. ~ o O O
_I ~ O O U~
O O 1~ 0 ~P
~ ~ o ~ ~
~1~ o 'a ~ h u~ 1~ 1 ~ S ~ a~
o o r~
O
O n~ C h Iq ~1 3 O ~ h 1~ -i O t~
O O
o u a~ o _~
:1 ~ o -I ~3 3 :~ U ~ U a~
_I ~ o ~ a) ~1 ~ ~ ~ o P ~ ~ u ~ ~ a~
U O S ~
U ~ ~ ~ (~ 0 ~ I h ,~ t U E~ a) u t) O ~ 1 to ~ h ~1 0 0 :1 o h ~ O --I ~ O ~:: h h ~
_l o a~ o o o o o P O ~ o ~ o ~ o o m u P1 u~ c~ u t¢ tn ~ u c~
Claims (6)
1. A process for preparing a particulate bleach activator composition containing A) from 40 to 95% by weight of pentaacetylglucose or a mixture of pentaacetylglucose and further customary bleach activators and B) from 5 to 60% by weight of one or more additives selected from the following classes:
(1) basic inorganic alkali metal and alkaline earth metal salts, (2) mono-, di- and trialkylamines, (3) chelating organic complexing agents combined with hydroxycarboxylic acids, (4) water-insoluble inorganic silicates, (5) anionic surfactants, (6) nonionic surfactants, (7) carboxyl-containing polymers and (8) polysaccharides, comprising the steps of (a) reacting glucose with acetic anhydride to give pentaacetylglucose, (b) removing the resulting acetic acid by distillation down to a residual level of from 0.2 to 10% by weight, (c) admixing the reaction mixture with one or more additives B and optionally further customary bleach activators, and (d) converting the product into a particulate form by a size-enlargement process.
(1) basic inorganic alkali metal and alkaline earth metal salts, (2) mono-, di- and trialkylamines, (3) chelating organic complexing agents combined with hydroxycarboxylic acids, (4) water-insoluble inorganic silicates, (5) anionic surfactants, (6) nonionic surfactants, (7) carboxyl-containing polymers and (8) polysaccharides, comprising the steps of (a) reacting glucose with acetic anhydride to give pentaacetylglucose, (b) removing the resulting acetic acid by distillation down to a residual level of from 0.2 to 10% by weight, (c) admixing the reaction mixture with one or more additives B and optionally further customary bleach activators, and (d) converting the product into a particulate form by a size-enlargement process.
2. A process for preparing a particulate bleach activator composition as claimed in claim 1, wherein component A is pentaacetylglucose alone.
3. A process for preparing a particulate bleach activator composition as claimed in claim 1, wherein the conversion step (d) is effected by extrusion.
4. A particulate bleach activator composition containing O.Z. 0050/41600 A) from 40 to 95% by weight of pentaacetylglucose or a mixture of pentaacetylglucose and further customary bleach activators, and B) from 5 to 60% by weight of one or more additives selected from the following classes:
(1) basic inorganic alkali metal and alkaline earth metal salts, (2) mono-, di- and trialkylamines, (3) chelating organic complexing agents combined with hydroxycarboxylic acids.
(1) basic inorganic alkali metal and alkaline earth metal salts, (2) mono-, di- and trialkylamines, (3) chelating organic complexing agents combined with hydroxycarboxylic acids.
5. A detergent containing from 0.5 to 20% by weight of a particulate bleach activator composition prepared as claimed in claim 1.
6. A detergent containing from 0.5 to 20% by weight of a particulate bleach activator composition as claimed in claim 4.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19904014978 DE4014978A1 (en) | 1990-05-10 | 1990-05-10 | METHOD FOR PRODUCING A GRAINY BLEACH ACTIVATOR COMPOSITION |
| DEP4014978.1 | 1990-05-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2041931A1 true CA2041931A1 (en) | 1991-11-11 |
Family
ID=6406102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2041931 Abandoned CA2041931A1 (en) | 1990-05-10 | 1991-05-07 | Preparation of a particulate bleach activator composition |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0456109A3 (en) |
| JP (1) | JPH04227800A (en) |
| CA (1) | CA2041931A1 (en) |
| DE (1) | DE4014978A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4134770A1 (en) * | 1991-10-22 | 1993-04-29 | Basf Ag | GRAINY BLEACH ACTIVATOR COMPOSITION |
| DE4143016A1 (en) * | 1991-12-24 | 1993-07-01 | Henkel Kgaa | BLEACH ACTIVATORS IN GRANULATE FORM (II) |
| DE4203169A1 (en) * | 1992-02-05 | 1993-08-12 | Basf Ag | GRAINY BLEACH ACTIVATOR COMPOSITION FROM HETEROGENEOUSLY GRADES |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD141844B1 (en) * | 1978-12-28 | 1982-04-28 | Rudolf Opitz | BLEACH |
| DE3268039D1 (en) * | 1981-09-28 | 1986-01-30 | Basf Ag | Granular bleach activator |
| EP0095904B1 (en) * | 1982-06-01 | 1986-09-03 | The Procter & Gamble Company | Detergent liquors and compositions for use therein |
| DE3337389A1 (en) * | 1983-10-14 | 1985-04-25 | Basf Ag, 6700 Ludwigshafen | METHOD FOR CRYSTALLIZING PENTAACETYL GLUCOSE |
| IT1180458B (en) * | 1984-03-22 | 1987-09-23 | Mira Lanza Spa | GRANULAR WHITENING ACTIVATOR AND ITS MANUFACTURING PROCESS |
| DE3615788A1 (en) * | 1986-05-10 | 1987-11-12 | Jentsch Guenther Dipl Chem Dr | LAUNDRY DETERGENT |
-
1990
- 1990-05-10 DE DE19904014978 patent/DE4014978A1/en not_active Withdrawn
-
1991
- 1991-04-26 JP JP9666491A patent/JPH04227800A/en not_active Withdrawn
- 1991-05-02 EP EP19910107077 patent/EP0456109A3/en not_active Withdrawn
- 1991-05-07 CA CA 2041931 patent/CA2041931A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04227800A (en) | 1992-08-17 |
| DE4014978A1 (en) | 1991-11-14 |
| EP0456109A3 (en) | 1992-04-01 |
| EP0456109A2 (en) | 1991-11-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5534196A (en) | Process for making lactam bleach activator containing particles | |
| FI67092B (en) | BLEKNINGSAKTIVATOR-KORN AVSEDDA FOER TVAETT- OCH / ELLER BLEKNINGSBLANDNINGAR | |
| EP0835926B1 (en) | Method of production of a coated bleach activator granule | |
| EP0656937A1 (en) | Dish-washing products with selected builder system. | |
| CH642678A5 (en) | Bleach and detergent. | |
| JP4272722B2 (en) | Synthesis of tertiary amine oxides | |
| CA2041931A1 (en) | Preparation of a particulate bleach activator composition | |
| US3956160A (en) | Heavy duty detergent powder and process for production of the same | |
| JP3081240B2 (en) | Bleaching of discolored surface active alkyl glycosides and method of treating bleached material | |
| US7122511B2 (en) | Process for the preparation of bleach activator granules | |
| US6165972A (en) | Solid surfactant mixtures comprising fatty acid polyhydroxyamides | |
| US6897192B2 (en) | Process for the preparation of bleach activator granules | |
| EP0746601A1 (en) | Granular washing or cleaning agent | |
| JPH05194997A (en) | Bleaching agent precursor | |
| US5510482A (en) | Process for bleaching discolored surface-active alkyl glycosides and for working up the bleached material | |
| WO1992009675A1 (en) | Stabilisation of percarbonate | |
| JP3510386B2 (en) | Process for producing granulated bleach activator, process for producing bleach or detergent containing granulated bleach activator | |
| WO1994009110A1 (en) | Method of manufacturing a granular washing and cleaning agent | |
| EP0937132A2 (en) | Process for preparing enzyme- and bleach-containing washing and cleaning agents | |
| JPH04359100A (en) | Production of high-bulk density detergent composition | |
| WO1996001887A1 (en) | Powdered bleaching and washing agent | |
| JPH08231578A (en) | Method of bleaching alkylpolyglycoside | |
| JPH02264789A (en) | Production of alkyl glycoside with favorable color and smell | |
| JPH029037B2 (en) | ||
| WO1993008254A1 (en) | Granular bleach-activator composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |