EP0614484B1 - Melange pulverulent d'agents tensioactifs - Google Patents
Melange pulverulent d'agents tensioactifs Download PDFInfo
- Publication number
- EP0614484B1 EP0614484B1 EP92923773A EP92923773A EP0614484B1 EP 0614484 B1 EP0614484 B1 EP 0614484B1 EP 92923773 A EP92923773 A EP 92923773A EP 92923773 A EP92923773 A EP 92923773A EP 0614484 B1 EP0614484 B1 EP 0614484B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- alkali metal
- formula
- alkylsulfate
- alkylglycoside
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 59
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 238000001035 drying Methods 0.000 claims abstract description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 15
- 238000001694 spray drying Methods 0.000 claims abstract description 14
- 230000009969 flowable effect Effects 0.000 claims abstract description 5
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 42
- -1 alkali metal hydrogen carbonate Chemical class 0.000 claims description 41
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- 239000003112 inhibitor Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 13
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- 150000001340 alkali metals Chemical group 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
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- 102000004190 Enzymes Human genes 0.000 claims description 7
- 108090000790 Enzymes Proteins 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 229910052910 alkali metal silicate Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
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- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- 238000006384 oligomerization reaction Methods 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 6
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 6
- 229910052681 coesite Inorganic materials 0.000 claims 2
- 229910052906 cristobalite Inorganic materials 0.000 claims 2
- 229910052682 stishovite Inorganic materials 0.000 claims 2
- 229910052905 tridymite Inorganic materials 0.000 claims 2
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims 1
- 239000003513 alkali Substances 0.000 abstract description 16
- 125000000217 alkyl group Chemical group 0.000 abstract description 10
- 239000004615 ingredient Substances 0.000 abstract description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 4
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- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 229930182470 glycoside Natural products 0.000 description 33
- 239000002002 slurry Substances 0.000 description 18
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- BGRWYDHXPHLNKA-UHFFFAOYSA-N Tetraacetylethylenediamine Chemical compound CC(=O)N(C(C)=O)CCN(C(C)=O)C(C)=O BGRWYDHXPHLNKA-UHFFFAOYSA-N 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
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- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 239000004435 Oxo alcohol Substances 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 239000004115 Sodium Silicate Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910052911 sodium silicate Inorganic materials 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 102000035195 Peptidases Human genes 0.000 description 2
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000003082 abrasive agent Substances 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
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- 150000004682 monohydrates Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- SHKKSBBWSHXOGZ-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-7-methyloctan-1-one Chemical compound CC(C)CCCCCC(=O)C1=CC=CC=C1O SHKKSBBWSHXOGZ-UHFFFAOYSA-N 0.000 description 1
- CMWPDPGTNAHDDB-UHFFFAOYSA-N 2-[2-[2-sulfo-4-(2,4,6-triamino-2h-1,3,5-triazin-1-yl)phenyl]ethenyl]-5-(2,4,6-triamino-2h-1,3,5-triazin-1-yl)benzenesulfonic acid Chemical class NC1N=C(N)N=C(N)N1C(C=C1S(O)(=O)=O)=CC=C1C=CC1=CC=C(N2C(=NC(N)=NC2N)N)C=C1S(O)(=O)=O CMWPDPGTNAHDDB-UHFFFAOYSA-N 0.000 description 1
- ZTGKHKPZSMMHNM-UHFFFAOYSA-N 3-(2-phenylethenyl)benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C=CC=2C=CC=CC=2)=C1S(O)(=O)=O ZTGKHKPZSMMHNM-UHFFFAOYSA-N 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/83—Mixtures of non-ionic with anionic compounds
-
- 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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/02—Preparation in the form of powder by spray drying
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/662—Carbohydrates or derivatives
Definitions
- the invention relates to powdered, pourable and free-flowing surfactant mixtures which contain alkyl sulfate, alkyl glycoside and inorganic carrier material, a process for their preparation and their use as premixes for the production of particulate detergents and cleaning agents.
- EPC international patent application WO-A-92/13938 powdery surfactant mixtures which are obtained by spray drying using drying gases at temperatures below 250 ° C. They contain 15% by weight to 50% by weight of alkyl sulfate, 1% by weight to 5% by weight of alkyl glycoside and 45% by weight to 80% by weight of inorganic carrier material, the weight ratio of alkyl sulfate to alkyl glycoside 25 : 1 to 8: 1.
- a process for the production of particulate detergents by drying a 40 to 80 percent aqueous slurry which, based on the resulting solid, 2 to 60% by weight of surfactants, which is at least 0.1 % By weight consist of alkyl glycosides, the total amount of alkyl glycosides being at most 2% by weight, containing 5 to 70% by weight builder substances and up to 40% by weight water-soluble fillers. In such slurries, the alkyl glycosides act as lower viscosity.
- Preferred surfactants are anionic surfactants, especially those of the alkylbenzenesulfonate type, and nonionic surfactants, especially ethoxylated fatty alcohols.
- the removal of water from the slurry is preferably accomplished by spray drying.
- the use of alkylbenzenesulfonate in detergents and cleaning agents has recently been called into question because of the petroleum base of this surfactant.
- sulfation products of compounds accessible from renewable raw materials come into consideration as more environmentally compatible surfactants with comparable good cleaning properties.
- aqueous slurries containing alkylbenzenesulfonate can be spray-dried without problems at the temperatures customary in such processes, normally about 250 ° C. to 350 ° C., there is a risk of spontaneous combustion in aqueous slurries which contain comparable amounts of other surfactants, in particular alkyl sulfates.
- the object was therefore to develop a process which allows the preparation of powdered surfactant mixtures free of alkylbenzenesulfonate by spray drying an aqueous surfactant-containing slurry without the self-ignition of the spray drying product occurring during production, the powdered products being said to be pourable and free-flowing.
- the water content in the powder product is not more than 20% by weight, in particular from 5% by weight to 15% by weight.
- the residual water content relates to the free water not bound in the crystal lattice.
- the process is preferably carried out in such a way that 3 to 10 parts by weight of alkyl sulfate according to formula I, 2 to 3 parts by weight of alkyl glycoside according to formula II and 25 to 80 parts by weight of the inorganic carrier material are mixed with so much water that at least 35% by weight, in particular A mixture containing 40% by weight to 50% by weight of water is formed.
- the phosphate-free, essentially inorganic carrier material preferably consists of 40% by weight to 60% by weight of alkali alumosilicate, in particular zeolite NaA and / or NaX, 20% by weight to 40% by weight of alkali carbonate, up to 20% by weight .-% of other inorganic salts, especially alkali silicates, alkali hydrogen carbonates and / or alkali chlorides, and not more than 20 wt .-% of organic material, especially alkali polycarboxylate.
- the further inorganic salts mentioned are contained in the support material in particular in amounts of 1% by weight to 10% by weight, the support material being free from alkali silicate with a molar ratio of SiO 2 to alkali oxide up to 2 and the proportion of alkali silicate with a The molar ratio of SiO 2 to alkali oxide over 2 is not more than 5% by weight, based in each case on the total support material.
- the carrier material is preferably also free of alkali sulfates.
- Alumosilicates suitable in the context of the invention have no particles with a grain size above 30 ⁇ m and preferably consist of at least 80% by weight of particles with a size below 10 ⁇ m.
- the polycarboxylates mentioned are known cobuilder substances in the form polymeric polycarboxylic acids or their water-soluble salts, in particular alkali salts, which can be obtained by polymerizing acrylic acid, methacrylic acid and / or maleic acid monomers or their salts. Such substances are contained in the carrier material preferably in amounts of 1% by weight to 15% by weight, in particular 5% by weight to 13% by weight, in each case based on the total carrier material.
- the preferred alkali metal for all of the ingredients mentioned is sodium.
- the spray-drying of the aqueous slurries takes place in systems usually provided for this purpose, so-called spray towers, in the upper part of which the slurry is sprayed into fine droplets by pressure nozzles, which move under the action of gravity into the lower part of the spray tower and come into contact with hot drying gases which are guided in cocurrent or preferably in countercurrent to the particles to be dried.
- the temperature of the drying gases is not so high that the temperature of the spray-dried particles rises above the self-ignition temperature of these particles.
- this means that the temperature of the drying gases does not exceed a value of 250 ° C. and is preferably in the range from 120 ° C. to 240 ° C., in particular from 140 ° C. to 210 ° C., the drying gas temperature being the hottest Location of the drying tower, the so-called ring channel, is measured.
- aqueous, generally 30 to 60 percent by weight alkyl glycoside pastes as are usually obtained in the course of alkyl glycoside production and, if appropriate, subsequent bleaching.
- the alkyl sulfate component and in particular the carrier component can be used as an aqueous solution or slurry.
- at least about 35% by weight, preferably 40 to 50% by weight. -% water is present in the slurry to be dried.
- a further advantage of the method according to the invention is that with values in the range from 3,000 mPa ⁇ s to 15,000 mPa ⁇ s at temperatures in the range mentioned surprisingly low viscosity of the slurries leading to the powdered surfactant mixtures according to the invention compared to slurries which contain the same amount of alkylbenzenesulfonate instead of alkyl sulfate.
- the powdery, pourable and free-flowing surfactant mixtures according to the invention produced by the process according to the invention contain 12% by weight to 25% by weight of alkyl sulfate of the formula I, R 1 -OSO 3 X (I) in which R 1 is an alkyl radical with 10 to 20 C atoms and X is an alkali, ammonium or alkyl or hydroxyalkyl-substituted ammonium ion, 2% by weight to 10% by weight alkyl glycoside of the formula II, R 2 -O (G) n (II) in which R 2 is an alkyl radical having 8 to 22 carbon atoms, G is a glycose unit and n is a number from 1 to 10, the weight ratio of alkyl sulfate to alkyl glycoside being 8: 1 to 1: 1, 45% by weight to 70 %
- an essentially inorganic carrier material which contains alkali carbonate and alkali alumosilicate in a weight ratio of 2:
- Suitable alkyl sulfates for use in the alkylbenzenesulfonate-free surfactant mixtures according to the invention are the compounds of the formula I in which R 1 is an alkyl radical having 10 to 20 carbon atoms and X is an alkali metal, ammonium or alkyl or hydroxyalkyl-substituted ammonium ion Question.
- R 1 is an alkyl radical having 10 to 20 carbon atoms
- X is an alkali metal, ammonium or alkyl or hydroxyalkyl-substituted ammonium ion Question.
- the derivatives of fatty alcohols with in particular 12 to 18 carbon atoms and their branched-chain analogs, the so-called oxo alcohols are particularly suitable.
- the alkyl sulfates can be prepared in a known manner by reacting the corresponding alcohol component with a conventional sulfating reagent, in particular sulfur trioxide or Chlorosulfonic acid, and subsequent neutralization with alkali, ammonium or alkyl or hydroxyalkyl-substituted ammonium bases.
- a conventional sulfating reagent in particular sulfur trioxide or Chlorosulfonic acid
- alkyl glycosides suitable for incorporation into the surfactant mixtures according to the invention are compounds of the general formula II in which R 2 is an alkyl radical having 8 to 22 carbon atoms, G is a glycose unit and n is a number between 1 and 10.
- R 2 is an alkyl radical having 8 to 22 carbon atoms
- G is a glycose unit
- n is a number between 1 and 10.
- the glycoside component ((G) n in formula II) of such alkyl glycosides are oligomers or polymers from naturally occurring aldose or ketose monomers, in particular glucose, mannose, fructose, galactose, talose, gulose, altrose, allose , Idose, ribose, arabinose, xylose and lyxose.
- the oligomers consisting of such glycosidically linked monomers are characterized not only by the type of sugar they contain, but also by their number, the so-called degree of oligomerization.
- the degree of oligomerization (n in formula II) generally assumes fractional numerical values as the quantity to be determined analytically; it is between 1 and 10, for the alkyl glycosides preferably used below 1.5, in particular between 1.2 and 1.4.
- the preferred monomer building block is glucose because of its good availability.
- the alkyl part (R 2 in formula II) of the alkyl glycosides contained in the surfactant mixtures according to the invention preferably also originates from easily accessible derivatives of renewable raw materials, in particular from fatty alcohols, although their branched chain isomers, in particular so-called oxo alcohols, can also be used to prepare usable alkyl glycosides. Accordingly, the primary alcohols with linear octyl, decyl, dodecyl, tetradecyl, hexadecyl or octadecyl radicals and mixtures thereof are particularly useful.
- the alkyl glycosides can be caused by production contain small amounts, for example 1 to 2%, of unreacted free fatty alcohol, which does not have a disadvantageous effect on the properties of the powder products produced therewith.
- alkyl glycosides are contained in the surfactant mixtures according to the invention in amounts of 2% by weight to 10% by weight, preferably 3% by weight to 8% by weight, the weight ratio of alkyl sulfate to alkyl glycoside being 8: 1 to 1: 1, preferably 5: 1 to 2: 1.
- the mixtures according to the invention can contain further surfactants, preferably nonionic surfactants and / or anionic surfactants and, in particular, fatty acid soaps with 8 to 22 carbon atoms, preferably 12 to 18 carbon atoms, and surfactants of the sulfate or sulfonate type, in amounts of preferably do not contain more than 5% by weight, in particular from 0.1% by weight to 3% by weight, in each case based on the total surfactant preparation.
- the sulfate-type surfactants which can also be used include the sulfated alkoxylation products of the alcohols mentioned, so-called ether sulfates.
- ether sulfates preferably contain 2 to 30, in particular 4 to 10, ethylene glycol groups per molecule.
- Suitable anionic surfactants also include the ⁇ -sulfoesters obtainable by reacting fatty acid esters with sulfur trioxide and subsequent neutralization, in particular those derived from fatty acids with 8 to 22 C atoms, preferably 12 to 18 C atoms, and linear alcohols with 1 to 6 C -Atoms, preferably 1 to 4 carbon atoms, derived sulfonation products.
- the nonionic surfactants in question include the alkoxylates, in particular the ethoxylates and / or propoxylates of linear or branched-chain alcohols having 10 to 22 carbon atoms, preferably 12 to 18 carbon atoms.
- the degree of alkoxylation of the alcohols is between 1 and 20, preferably between 3 and 10. They can be prepared in a known manner by reacting the corresponding alcohols with the corresponding alkylene oxides.
- the derivatives of fatty alcohols are particularly suitable, although their branched chain isomers, in particular so-called oxo alcohols, can also be used to prepare alkoxylates which can be used.
- the ethoxylates of primary alcohols with linear dodecyl, tetradecyl, hexadecyl or octadecyl radicals are particularly useful as well as their mixtures.
- Corresponding ethoxylation and / or propoxylation products of alkylamines, vicinal diols and carboxamides which correspond to the alcohols mentioned with regard to the alkyl part can also be used.
- the preparations according to the invention can contain small amounts, preferably not more than 5% by weight in total, of further constituents customary in detergents and cleaning agents which are stable under the spray drying conditions.
- These optional components include, in particular, complexing agents for heavy metals, for example aminopolycarboxylic acids, aminohydroxypolycarboxylic acids, polyphosphonic acids and / or aminopolyphosphonic acids, graying inhibitors, for example cellulose ethers, foam inhibitors, for example organopolysiloxanes or paraffins, and optical brighteners, for example stilbene disulfonic acid.
- the surfactant mixtures according to the invention do not contain more than 1% by weight, in particular 0.01% by weight to 0.5% by weight, of optical brighteners, in particular compounds from the class of the substituted 4,4'-bis (2, 4,6-triamino-s-triazinyl) -stilbene-2,2'-disulfonic acids, not more than 5% by weight, in particular 0.1% by weight to 2% by weight, of complexing agents for heavy metals, in particular aminoalkylenephosphonic acids and their Salts, not more than 3% by weight, in particular 0.5% by weight to 2% by weight, of graying inhibitors and not more than 2% by weight, in particular 0.1% by weight to 1% by weight, of foam inhibitors , wherein the weight percentages relate to the total surfactant mixture.
- optical brighteners in particular compounds from the class of the substituted 4,4'-bis (2, 4,6-triamino-s-triazinyl) -stilbene-2,2'-disulfonic acids, not
- the powdered surfactant mixtures according to the invention are used in particular as pourable and free-flowing precursors for the production of particulate detergents or cleaning agents.
- the powders according to the invention should have average grain sizes of preferably 0.2 mm to 0.4 mm and should be largely free of particles with diameters of more than 2 mm or less than 50 ⁇ m. These limits are normally met by the surfactant mixtures obtained by spray drying, otherwise particles outside this size range can be removed by simple sieving and in the manufacturing process to be led back.
- the bulk density of the powder products according to the invention is preferably between 400 and 600 grams per liter. If desired, their liter weight can be increased by, in principle, the usual compression, if they are to be used for the production of washing or cleaning agents with a high liter weight, so-called heavy powders.
- the preparations according to the invention are free-flowing, free-flowing powders which do not lose their advantageous properties even after prolonged storage. They are also lightening-free, light-colored, have an acceptable odor and show no tendency to clump. In contrast, strong clumping was found in powders which contained the same amounts of alkylbenzenesulfonate instead of alkyl sulfate. Such products were also unacceptably colored brown, even if they contained only relatively small amounts of alkyl glycoside, for example 3% by weight or less. All the more surprising are the unexpectedly positive properties of the surfactant mixtures according to the invention.
- the surfactant mixtures according to the invention can be mixed in a manner known in principle with other constituents which are customary in such agents, such as bleaching agents, bleach activators, enzymes, foam inhibitors, optical brighteners, graying inhibitors, for example cellulose ethers and abrasives , for example quartz flour, belong.
- the spraying of liquid, liquefied or dissolved ingredients, for example liquid enzymes, dyes, fragrances or other surfactants, in particular nonionic surfactants, onto the powders according to the invention is also possible in a manner known in principle.
- the surfactant mixtures according to the invention are preferably used in amounts of from 50% by weight to 80% by weight, in particular from 65% by weight to 75% by weight, in each case based on the total agent, in the production of cleaning or washing agents. In particular for the production of cleaning agents, it is possible for the remainder to consist of 100% by weight of abrasives. Additional, in particular nonionic, surfactant is present in such washing or cleaning agents, with the exclusion of any surfactant mixture according to the invention Contained amount, preferably in amounts not more than 5 wt .-%, in particular from 0.5 wt .-% to 2 wt .-%, each based on the total agent.
- Suitable foam inhibitors include long-chain soaps, in particular beech soap, fatty acid amides, paraffins, waxes, microcrystalline waxes, organopolysiloxanes and mixtures thereof, which may also contain microfine, optionally silanized or otherwise hydrophobized silica.
- foam inhibitors are preferably bound to granular, water-soluble carrier substances, as described, for example, in German patent application DE 34 36 194, European patent applications EP 262 588, EP 301 414, EP 309 931 or European patent EP 150 386.
- foam inhibitors are preferably present in amounts not exceeding 1% by weight, in particular from 0.1% by weight to 1% by weight, in each case based on entire agent and including the amount that may be contained in the surfactant mixture according to the invention.
- the bleaching agents which are suitable as further constituents of such agents are the per compounds which are generally used in detergents, such as perborate, which can be present as a tetra- or monohydrate, percarbonate, perpyrophosphate and persilicate, which are generally present as alkali metal salts, in particular as sodium salts.
- Such bleaches are contained in detergents or cleaning agents produced using surfactant mixtures according to the invention, preferably in amounts not exceeding 25% by weight, in particular from 12% by weight to 20% by weight, in each case based on the total agent.
- the component of the bleach activators comprises the commonly used N- or O-acyl compounds, for example multiply acylated alkylenediamines, in particular tetraacetylethylenediamine, acylated glycolurils, in particular tetraacetylglycoluril, N-acylated hydantoins, hydrazides, triazoles, urazoles, diketopiperazines, sulfurylamides, and carbonic acid urate amides and cyanonicuronides and also cyanonicuronides Phthalic anhydride, carboxylic acid esters, especially sodium isononanoyl phenol sulfonate, and acylated sugar derivatives, especially pentaacetyl glucose.
- N- or O-acyl compounds for example multiply acylated alkylenediamines, in particular tetraacetylethylenediamine, acylated glycolurils, in particular tetraacetylgly
- the bleach activators can be coated or granulated with coating substances in a known manner in order to avoid the interaction with the per-compounds during storage, with the aid of carboxymethyl cellulose granulated tetraacetyl ethylenediamine with average grain sizes of 0.01 mm to 0.8 mm, as described, for example, by can be prepared in the method described in European Patent EP 037 026, is particularly preferred.
- Bleach activators of this type are preferably contained in amounts of not more than 10% by weight, in particular from 2% by weight to 8% by weight, in each case based on the total agent, in detergents or cleaning agents produced using surfactant mixtures according to the invention.
- Suitable enzymes are those from the class of proteases, lipases, amylases and cellulases and their mixtures, which are stable and active even under the temperature conditions of white washing. Enzymes obtained from fungi or bacterial strains such as Bacillus subtilis, Bacillus licheniformis, Bacillus lentus and Streptomyces griseus are preferably used. The enzymes used can be adsorbed onto carrier substances in a known manner, embedded in coating substances and / or granulated with the aid of carrier substances in order to make them easier to handle and to protect them against premature inactivation.
- Such enzymes are preferably in amounts of not more than 2% by weight, in particular from 0.4% by weight to 1.2% by weight, in each case based on the total in washing or cleaning agents produced using surfactant mixtures according to the invention Means included.
- the detergents and cleaning agents produced using the surfactant mixtures according to the invention are stable in storage, free-flowing and stable in color.
- a further advantage is that when the surfactant mixtures according to the invention are used, largely inert filler salts, in particular alkali metal sulfate, can be dispensed with.
- An aqueous slurry containing 44% by weight of water was produced from the raw materials listed in Table 1.
- the free-flowing powder M1 characterized in Table 1 by its composition was obtained with an average grain size of around 0.5 mm, which was free of particles larger than 1.8 mm in diameter, had dust contents of 0.15% by weight and a bulk density of Had 540 grams per liter.
- a powder was prepared from the same amounts of the same raw materials as for product M1 under otherwise identical conditions, which contained only half of the stated amount of alkyl glycoside from the sprayed slurry and which the remaining amount of alkyl glycoside by spraying a highly concentrated aqueous solution of this Ingredient was added. Despite the increased tendency to clump, this product also had significantly higher dust content than product M1 .
- the detergent W1 was prepared by simply mixing the amount of the powder according to the invention stated in the table below with conventional detergent ingredients .
- this showed an average of all soiling at 30 ° C as well as at 60 ° C and 90 ° C a washing power that reached at least the level of a commercial heavy-duty detergent with a fatty alkyl polyethoxylate / alkylbenzenesulfonate surfactant component tested for comparison purposes.
- the agent according to the invention performed significantly better, especially in the case of cosmetic soiling.
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Claims (14)
- Procédé de fabrication de mélanges pulvérulents de tensioactifs, contenant de l'alkylsulfate, de l'alkylglycoside et une matière porteuse inorganique, par séchage de mélanges de tensioactifs aqueux, coulants, caractérisé en ce que l'on mélange 2 à 15 parties en poids d'alkylsulfate de la formule I,
R1-OSO3X (I)
dans laquelle R1 représente un radical alkyle comportant 10 à 20 atomes de C et X correspond à un ion de métal alcalin, d'ammonium ou d'ammonium à substitution alkyle ou hydroxyalkyle, une quantité de 1 à 5 parties en poids d'alkylglycoside de la formule II,
R2-O(G)n (II)
dans laquelle R2 représente un radical alkyle comportant 8 à 22 atomes de C, G correspond à une unité d'ose et n est un nombre de 1 à 10, l'alkylsulfate et l'alkylglycoside étant entre eux dans un rapport pondéral compris entre 8:1 et 1:1, de préférence entre 5:1 et 2:1, et une quantité de 20 à 100 parties en poids d'une matière porteuse sans phosphates essentiellement inorganique, qui contient du carbonate de métal alcalin et de l'aluminosilicate de métal alcalin dans un rapport pondéral de 2:1 à 1:3, avec autant d'eau que nécessaire pour obtenir un mélange coulant et pompable aux températures inférieures à 95 °C, présentant une viscosité de 3 000 à 15 000 mPa.s, déterminée entre 60 et 80 °C, et que l'on extrait l'eau de celui-ci par séchage par pulvérisation en utilisant des gaz de séchage à des températures inférieures à 250 °C, jusqu'à ce que l'on obtienne un produit pulvérulent coulant, l'alkylsulfate et l'alkylglycoside étant entre eux dans un rapport pondéral n'atteignant pas 8:1, si l'alkylsulfate de la formule I est contenu dans une proportion de 15 parties en poids. - Procédé selon la revendication 1, caractérisé en ce que l'on mélange 3 à 10 parties en poids d'alkylsulfate conforme à la formule 1, 2 à 3 parties en poids d'alkylglycoside selon la formule II et 25 à 80 parties en poids de la matière porteuse inorganique avec autant d'eau que nécessaire pour obtenir un mélange contenant au moins 35 % en poids, en particulier 40 à 50 % en poids d'eau.
- Procédé selon la revendication 1 ou 2, caractérisé en ce que l'alkylsulfate et l'alkylglycoside sont entre eux dans un rapport pondéral de 5:1 à 2:1.
- Procédé selon une des revendications 1 à 3, caractérisé en ce que l'on utilise des gaz de séchage à des températures de 120 à 240 °C, en particulier de 140 à 210 °C.
- Procédé selon une des revendications 1 à 4, caractérisé en ce que la matière porteuse inorganique contient 40 à 60 % en poids d'aluminosilicate de métal alcalin, en particulier de la zéolithe NaA et/ou NaX, 20 à 40 % en poids de carbonate de métal alcalin, jusqu'à 20 % en poids d'autres sels inorganiques et pas plus de 20 % en poids de matière organique, en particulier du polycarboxylate.
- Procédé selon une des revendications 1 à 5, caractérisé en ce que la matière porteuse inorganique contient en plus de l'aluminosilicate de métal alcalin et du carbonate de métal alcalin, 1 à 10 % en poids - dans chaque cas par rapport à la totalité de la matière porteuse - d'hydrogénocarbonate de métal alcalin, de chlorure de métal alcalin ou de silicate de métal alcalin ou un mélange de ceux-ci, la matière porteuse étant exempte de silicate de métal alcalin avec un rapport molaire entre le SiO2 et l'oxyde de métal alcalin allant jusqu'à 2 et la proportion de silicate de métal alcalin avec un rapport molaire entre le SiO2 et l'oxyde de métal alcalin supérieur à 2 ne dépassant pas 5 % en poids, par rapport à la totalité de la matière porteuse.
- Procédé selon une des revendications 1 à 6, caractérisé en ce que la matière inorganique porteuse contient en plus de l'aluminosilicate de métal alcalin et du carbonate de métal alcalin, 1 à 15 % en poids, en particulier de 5 à 13 % en poids, dans chaque cas par rapport à la totalité de la matière porteuse inorganique, de sel soluble dans l'eau d'acides polycarboxyliques polymères, qui peuvent être fabriqués par polymérisation de monomères d'acide acrylique, méthacrylique et/ou maléique ou de sels de ceux-ci.
- Mélange pulvérulent de tensioactifs, déversable et coulant, qui est obtenu par séchage par pulvérisation, en utilisant des gaz de séchage à des températures inférieures à 250 °C, d'un mélange aqueux versable de ses constituants, et qui contient
12 à 25 % en poids d'alkylsulfate de la formule I,
R1-OSO3X (I)
dans laquelle R1 représente un radical alkyle comportant 10 à 20 atomes de C et X correspond à un ion de métal alcalin, d'ammonium ou d'ammonium à substitution alkyle ou hydroxyalkyle,
2 à 10 % en poids d'alkylglycoside de la formule II,
R2-O(G)n (II)
dans laquelle R2 représente un radical alkyle comportant 8 à 22 atomes de C, G correspond à une unité d'ose et n est un nombre de 1 à 10, l'alkylsulfate et l'alkylglycoside étant entre eux dans un rapport pondéral compris entre 8:1 et 1:1,45 à 70 % en poids d'une matière porteuse essentiellement inorganique, qui contient du carbonate de métal alcalin et de l'aluminosilicate de métal alcalin dans un rapport pondéral de 2:1 à 1:3,pas plus de 5 % en poids, en particulier 0,1 à 3 % en poids d'un autre tensioactif,pas plus de 1 % en poids, en particulier 0,01 à 0,5 % en poids d'un agent de blanchiment optique,pas plus de 2 % en poids, en particulier 0,1 à 1 % en poids d'un inhibiteur de mousse,pas plus de 3 % en poids, en particulier 0,5 à 2 % en poids d'un inhibiteur de ternissement,pas plus de 5 % en poids, en particulier 0,1 à 2 % en poids d'un complexant pour les métaux lourds, etjusqu'à 20 % en poids d'eau, l'alkylsulfate et l'alkylglycoside étant entre eux dans un rapport pondéral n'atteignant pas 8:1 si l'alkylsulfate de la formule I est contenu dans une proportion de 15 % en poids. - Mélange de tensioactifs selon la revendication 8, caractérisé en ce qu'il contient 3 à 8 % en poids d'alkylglycoside selon la formule II, 52 à 65 % de matière porteuse et 5 à 15 % en poids d'eau.
- Mélange de tensioactifs selon la revendication 8 ou 9, caractérisé en ce que l'alkylsulfate de la formule I possède un radical alkyle R1 comportant 12 à 18 atomes de C.
- Mélange de tensioactifs selon une des revendications 8 à 10, caractérisé en ce que l'alkylglycoside de la formule II est un alkylglucoside et qu'il possède un degré d'oligomérisation n inférieur à 1,5, en particulier de 1,2 à 1,4.
- Utilisation, comme prémélange déversable et coulant pour la fabrication de produits de lavage ou de nettoyage sous forme granulaire, d'un mélange pulvérulent de tensioactifs, déversable et coulant, qui est obtenu par séchage par pulvérisation, en utilisant des gaz de séchage à des températures inférieures à 250 °C, d'un mélange aqueux versable de ses constituants, et qui contient
10 à 30 % en poids d'alkylsulfate de la formule I,
R1-OSO3X (I)
dans laquelle R1 représente un radical alkyle comportant 10 à 20 atomes de C et X correspond à un ion de métal alcalin, d'ammonium ou d'ammonium à substitution alkyle ou hydroxyalkyle,
2 à 10 % en poids d'alkylglycoside de la formule II,
R2-O(G)n (II)
dans laquelle R2 représente un radical alkyle comportant 8 à 22 atomes de C, G correspond à une unité d'ose et n est un nombre de 1 à 10, l'alkylsulfate et l'alkylglycoside étant entre eux dans un rapport pondéral compris entre 8:1 et 1:1,45 à 70 % en poids d'une matière porteuse essentiellement inorganique, qui contient du carbonate de métal alcalin et de l'aluminosilicate de métal alcalin dans un rapport pondéral de 2:1 à 1:3,pas plus de 5 % en poids, en particulier 0,1 à 3 % en poids d'un autre tensioactif,pas plus de 1 % en poids, en particulier 0,01 à 0,5 % en poids d'un agent de blanchiment optique,pas plus de 2 % en poids, en particulier 0,1 à 1 % en poids d'un inhibiteur de mousse,pas plus de 3 % en poids, en particulier 0,5 à 2 % en poids d'un inhibiteur de ternissement,pas plus de 5 % en poids, en particulier 0,1 à 2 % en poids d'un complexant pour les métaux lourds, etl'alkylsulfate et l'alkylglycoside étant entre eux dans un rapport pondéral n'atteignant pas 8:1 si l'alkylsulfate de la formule I est contenu dans une proportion de 15 % en poids.
jusqu'à 20 % en poids d'eau, - Utilisation, comme prémélange déversable et coulant pour la fabrication de produits de lavage ou de nettoyage sous forme granulaire, d'un mélange pulvérulent de tensioactifs selon une des revendications 8 à 11.
- Utilisation selon la revendication 12 ou 13,
caractérisée en ce que le produit obtenu contient50 à 80 % en poids, en particulier, 65 à 75 % en poids d'un mélange de tensioactifs selon une des revendications 8 à 11,jusqu'à 25 % en poids, en particulier 12 à 20 % en poids, d'agent de blanchimentjusqu'à 10 % en poids, en particulier, 2 à 8 % en poids d'activateur de blanchiment,jusqu'à 1 % en poids, en particulier, 0,1 à 1 % en poids d'inhibiteur de mousse,jusqu'à 2 % en poids, en particulier, 0,4 à 1,2 % en poids d'enzyme,jusqu'à 50 % en poids, en particulier, 25 à 35 % en poids, de matière abrasive etjusqu'à 5 % en poids, en particulier 0,5 à 2 % en poids de tensioactif, en particulier, non ionique supplémentaire.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4139551A DE4139551A1 (de) | 1991-11-30 | 1991-11-30 | Pulverfoermige tensidmischung |
DE4139551 | 1991-11-30 | ||
PCT/EP1992/002694 WO1993011212A1 (fr) | 1991-11-30 | 1992-11-23 | Melange pulverulent d'agents tensioactifs |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0614484A1 EP0614484A1 (fr) | 1994-09-14 |
EP0614484B1 true EP0614484B1 (fr) | 1997-04-09 |
Family
ID=6445990
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92923773A Expired - Lifetime EP0614484B1 (fr) | 1991-11-30 | 1992-11-23 | Melange pulverulent d'agents tensioactifs |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0614484B1 (fr) |
JP (1) | JPH07501564A (fr) |
AT (1) | ATE151452T1 (fr) |
DE (2) | DE4139551A1 (fr) |
ES (1) | ES2100367T3 (fr) |
WO (1) | WO1993011212A1 (fr) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19524464C2 (de) * | 1995-07-10 | 2000-08-24 | Cognis Deutschland Gmbh | Verfahren zur Herstellung von Zuckertensidgranulaten |
US5571446A (en) * | 1995-07-27 | 1996-11-05 | Diversey Corporation | Anionic stabilized enzyme based clean-in-place system |
DE19624637A1 (de) * | 1996-06-21 | 1998-01-02 | Henkel Kgaa | Waschverfahren für Textilien mit verbesserten Pflegeeigenschaften |
GB2318584A (en) * | 1996-10-25 | 1998-04-29 | Procter & Gamble | Process for preparing detergent compositions by spray drying |
DE19710153C1 (de) | 1997-03-12 | 1998-02-12 | Henkel Kgaa | Verfahren zur Herstellung neutraler Zuckertensidgranulate |
EP0879876A1 (fr) * | 1997-05-21 | 1998-11-25 | The Procter & Gamble Company | Procédé de préparation d'une composition détergente granulaire ou d'un composant comprenant un agent tensioactif soluble dans l'eau |
DE10018812A1 (de) | 2000-04-15 | 2001-10-25 | Cognis Deutschland Gmbh | Verfahren zur Herstellung von nichtionischen Tensidgranulaten |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4536319A (en) * | 1983-10-04 | 1985-08-20 | The Procter & Gamble Company | Compositions comprising alkylpolysaccharide detergent surfactant |
WO1990004630A1 (fr) * | 1988-10-21 | 1990-05-03 | Henkel Corporation | Procede de preparation d'une boue detergente et d'une composition detergente particulaire |
DE4102745A1 (de) * | 1991-01-30 | 1992-08-06 | Henkel Kgaa | Pulverfoermige tensidmischung |
-
1991
- 1991-11-30 DE DE4139551A patent/DE4139551A1/de not_active Withdrawn
-
1992
- 1992-11-23 WO PCT/EP1992/002694 patent/WO1993011212A1/fr active IP Right Grant
- 1992-11-23 EP EP92923773A patent/EP0614484B1/fr not_active Expired - Lifetime
- 1992-11-23 DE DE59208338T patent/DE59208338D1/de not_active Expired - Fee Related
- 1992-11-23 AT AT92923773T patent/ATE151452T1/de not_active IP Right Cessation
- 1992-11-23 JP JP5509779A patent/JPH07501564A/ja active Pending
- 1992-11-23 ES ES92923773T patent/ES2100367T3/es not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
ATE151452T1 (de) | 1997-04-15 |
ES2100367T3 (es) | 1997-06-16 |
EP0614484A1 (fr) | 1994-09-14 |
DE4139551A1 (de) | 1993-06-03 |
JPH07501564A (ja) | 1995-02-16 |
DE59208338D1 (de) | 1997-05-15 |
WO1993011212A1 (fr) | 1993-06-10 |
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