EP1765967B1 - Mischpulver oder mischgranulat auf basis von mgda - Google Patents
Mischpulver oder mischgranulat auf basis von mgda Download PDFInfo
- Publication number
- EP1765967B1 EP1765967B1 EP05756996.4A EP05756996A EP1765967B1 EP 1765967 B1 EP1765967 B1 EP 1765967B1 EP 05756996 A EP05756996 A EP 05756996A EP 1765967 B1 EP1765967 B1 EP 1765967B1
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- EP
- European Patent Office
- Prior art keywords
- mixed
- powder
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- weight
- mixture
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 40
- 239000008187 granular material Substances 0.000 title claims description 29
- 239000000843 powder Substances 0.000 title claims description 20
- 239000002736 nonionic surfactant Substances 0.000 claims description 43
- -1 alkali metal salt Chemical class 0.000 claims description 30
- 239000011812 mixed powder Substances 0.000 claims description 23
- 239000003599 detergent Substances 0.000 claims description 17
- 239000002202 Polyethylene glycol Substances 0.000 claims description 16
- 229920001223 polyethylene glycol Polymers 0.000 claims description 16
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical class OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 15
- CIEZZGWIJBXOTE-UHFFFAOYSA-N 2-[bis(carboxymethyl)amino]propanoic acid Chemical compound OC(=O)C(C)N(CC(O)=O)CC(O)=O CIEZZGWIJBXOTE-UHFFFAOYSA-N 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 13
- 229930195729 fatty acid Natural products 0.000 claims description 13
- 239000000194 fatty acid Substances 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 150000002191 fatty alcohols Chemical class 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 150000003138 primary alcohols Chemical class 0.000 claims description 4
- 238000007493 shaping process Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000001694 spray drying Methods 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 3
- 238000005469 granulation Methods 0.000 claims description 3
- 230000003179 granulation Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 238000004900 laundering Methods 0.000 claims 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 41
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 229920002535 Polyethylene Glycol 1500 Polymers 0.000 description 5
- 239000002738 chelating agent Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- VUYXVWGKCKTUMF-UHFFFAOYSA-N tetratriacontaethylene glycol monomethyl ether Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO VUYXVWGKCKTUMF-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000004851 dishwashing Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920005646 polycarboxylate Polymers 0.000 description 4
- 239000013042 solid detergent Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
- 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 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000006268 reductive amination reaction Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 125000006539 C12 alkyl 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 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 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 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000004697 chelate complex Chemical class 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000007909 melt granulation Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/33—Amino carboxylic acids
-
- 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
-
- 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
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- 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
- C11D1/825—Mixtures of compounds all of which are non-ionic
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3707—Polyethers, e.g. polyalkyleneoxides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3753—Polyvinylalcohol; Ethers or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
- C11D3/3776—Heterocyclic compounds, e.g. lactam
Definitions
- the invention relates to a mixed powder or mixed granules based on glycine-N, N-diacetic acid or derivatives thereof.
- solid or liquid formulations can be selected.
- Solid formulations may be present, for example, as powders or granules.
- the preparation of individual powder or granular detergent ingredients or ingredient mixtures may be difficult or impossible depending on the nature of the ingredients.
- the powder or granules must not cake together during preparation, mixing and storage of the means and should not affect the spreading or flowability of the powder or granules.
- the WO 95/29216 relates to detergent powder compositions containing a metal ion chelate complex and an anionic functionalized polymer.
- the detergent powder contains a complex of a chelating agent and a metal ion selected from magnesium, calcium, strontium, zinc and aluminum as well as a polymer having in particular carboxyl groups.
- the powder is prepared by spray drying.
- the chelating agents may be selected from a variety of compounds, but glycine-N, N-diacetic acid derivatives are not mentioned.
- polycarboxylates containing water-soluble salts of homo- and copolymers of aliphatic carboxylic acids.
- the EP-A-0 618 289 relates to highly active granular detergent compositions containing chelates and polymers.
- the composition comprises an anionic surfactant, a chelating agent and a polymer or copolymer.
- the chelating agents may be selected from a variety of compounds. However, glycine-N, N-diacetic acid derivatives are not listed.
- polymers in particular polycarboxylates such as polyacrylates are listed.
- glycine-N, N-diacetic acid derivatives as complexing agents for alkaline earth and heavy metal ions in detergents and cleaners is in the EP-A-0 845 456 described.
- MGDA derivatives glycine-N, N-diacetic acid derivatives
- a special crystallization process is used.
- the bulk and flowability of the powder or granules should be preserved.
- N-diacetic acid derivatives with polycarboxylates has the advantage that o.g. Distinguish mixtures by improved flowability.
- M is an alkali metal, preferably sodium or potassium, more preferably sodium.
- R is a C 1-12 -alkyl radical, preferably a C 1-6 -alkyl radical, more preferably a methyl or ethyl radical.
- Particularly preferred component (a) used is an alkali metal salt of methylglycinediacetic acid (MGDA). Most preferably, the trisodium salt of methylglycinediacetic acid is used.
- At least one polyethylene glycol or at least one nonionic surfactant with at least one polyethylene glycol is used.
- As component (b) is preferably used a polyethylene glycol, more preferably having an average molecular weight (weight average molecular weight) of 500 to 30,000 g / mol.
- the polyethylene glycol used as component (b) has OH end groups and / or C 1-6 -alkyl end groups.
- a polyethylene glycol which has OH and / or methyl end groups is particularly preferred.
- the polyethylene glycol used in the mixture according to the invention has a molecular weight (weight average molecular weight) of 1000 to 5000 g / mol, most preferably from 1200 to 2000 g / mol.
- nonionic surfactants can be used as component (b). These are preferably selected from the group consisting of alkoxylated, primary alcohols, alkoxylated fatty alcohols, alkyl glycosides, alkoxylated fatty acid alkyl esters, amine oxides and polyhydroxy fatty acid amides.
- nonionic surfactants are preferably alkoxylated, advantageously ethoxylated, in particular primary alcohols having preferably 8 to 18 carbon atoms and an average of 1 to 12 moles of ethylene oxide (EO) per mole of alcohol used, in which the alcohol residue may linear or preferably methyl-branched in the 2-position or may contain linear and branched radicals in the mixture, as they are usually present in Oxoalkoholresten.
- EO ethylene oxide
- alcohol ethoxylates with linear radicals of alcohols of natural origin having 12 to 18 carbon atoms, for example of coconut, palm, tallow or oleyl alcohol, and on average 2 to 8 EO per mole of alcohol are preferred.
- the preferred ethoxylated alcohols include, for example, C 12-14 alcohols containing 3 EO, 4 EO or 7 EO, C 9-11 alcohols with 7 EO, C 13-15 alcohols with 3 EO, 5 EO, 7 EO or 8 EO, C 12-18 -alcohols with 3 EO, 5 EO or 7 EO and mixtures of these, such as mixtures of C 12-14 -alcohol with 3 EO and C 12-14 -alcohol with 7 EO.
- the degrees of ethoxylation given represent statistical means that may be a whole or fractional number for a particular product.
- Preferred alcohol ethoxylates have a narrow homolog distribution ("narrow range ethoxylates", NRE).
- fatty alcohols with more than 12 EO can also be used. Examples include tallow fatty alcohols with 14 EO, 25 EO, 30 EO or 40 EO.
- Nonionic surfactants containing EO and PO groups together in the molecule can also be used according to the invention.
- block copolymers with EO-PO block units, or PO-EO block units can be used, but also EO-PO-EO copolymers or PO-EO-PO copolymers.
- nonionic surfactants and alkyl glycosides of the general formula RO (G) can be used, in which R is a primary straight-chain or methyl-branched especially in the 2-position methyl-branched aliphatic radical having 8 to 22, preferably 12 to 18 carbon atoms and G the symbol is that which represents a glycose unit having 5 or 6 C atoms, preferably glycose.
- the degree of oligomerization x which indicates the distribution of monoglycosides and oligoglycosides, is any number between 1 and 10; preferably x is 1.2 to 1.4.
- nonionic surfactants used either as the sole nonionic surfactant or in combination with other nonionic surfactants are alkoxylated, preferably ethoxylated or ethoxylated and propoxylated fatty acid alkyl esters, preferably having from 1 to 4 carbon atoms in the alkyl chain, especially fatty acid methyl esters.
- Nonionic surfactants of the amine oxide type for example N-tallowalkyl-N, N-dihydroxyethylamine oxide, and the fatty acid alkanolamides may also be suitable.
- the amount of these nonionic surfactants is preferably not more than that of the ethoxylated fatty alcohols, especially not more than half thereof.
- nonionic surfactants are polyhydroxy fatty acid amides of the formula (II)
- the polyhydroxy fatty acid amides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.
- the group of polyhydroxy fatty acid amides also includes compounds of the formula (III)
- R 2 is a linear, branched or cyclic alkyl radical or an aryl radical having 2 to 8 carbon atoms
- R 3 is a linear, branched or cyclic Alkyl radical or an aryl radical or an oxy-alkyl radical having 1 to 8 carbon atoms, wherein C 1-4 alkyl or phenyl radicals are preferred and (Z) is a linear polyhydroxyalkyl radical whose alkyl chain is substituted with at least two hydroxyl groups, or alkoxylated, preferably ethoxylated or propoxylated, derivatives of this radical.
- (Z) is preferably obtained by reductive amination of a sugar, for example Glucose, fructose, maltose, lactose, galactose, mannose or xylose.
- a sugar for example Glucose, fructose, maltose, lactose, galactose, mannose or xylose.
- the N-alkoxy- or N-aryloxy-substituted compounds can then be converted into the desired polyhydroxy fatty acid amides by reaction with fatty acid methyl esters in the presence of an alkoxide as catalyst.
- nonionic surfactants are preferably used which have a melting point above room temperature. Accordingly, preferred blends are characterized by containing nonionic surfactant (s) having a melting point above 20 ° C, preferably above 25 ° C, more preferably from 25 to 100 ° C, and most preferably from 30 to 50 ° C , contain.
- Suitable nonionic surfactants which have melting and softening points in the temperature range mentioned are, for example, low-foam nonionic surfactants which may be solid or highly viscous at room temperature. If highly viscous nonionic surfactants are used at room temperature, it is preferred that they have a viscosity above 20 Pas, preferably above 35 Pas and in particular above 40 Pas. Nonionic surfactants which have a waxy consistency at room temperature are also preferred.
- Preferred nonionic surfactants to be used at room temperature are from the groups of the alkoxylated nonionic surfactants, in particular the ethoxylated primary alcohols and mixtures of these surfactants with structurally complicated surfactants such as polyoxypropylene / polyoxyethylene / polyoxypropylene (PO / EO / PO) surfactants.
- Such nonionic (PO / EO / PO) surfactants are also characterized by good foam control.
- the nonionic surfactant having a melting point above room temperature is an ethoxylated nonionic surfactant resulting from the reaction of a monohydroxyalkanol or alkylphenol having 6 to 20 carbon atoms, preferably at least 12 mol, more preferably at least 15 mol, especially at least 20 mol, ethylene oxide per mole of alcohol or alkylphenol emerged.
- a particularly preferred nonionic surfactant which is solid at room temperature is selected from a straight-chain fatty alcohol having 16 to 20 C atoms (C 16-20 -alcohol), preferably a C 18 -alcohol and at least 12 moles, preferably at least 15 moles and especially at least 20 moles, of ethylene oxide.
- C 16-20 -alcohol a straight-chain fatty alcohol having 16 to 20 C atoms
- C 18 -alcohol preferably a C 18 -alcohol and at least 12 moles, preferably at least 15 moles and especially at least 20 moles, of ethylene oxide.
- the so-called “narrow range ethoxylates" are particularly preferred.
- particularly preferred mixtures according to the invention comprise ethoxylated (s), nonionic surfactant (s) which are prepared from C 6-20 monohydroxyalkanols or C 6-20 alkylphenols or C 16-20 fatty alcohols and more than 12 mol, preferably more than 15 moles and in particular more than 20 moles of ethylene oxide per mole of alcohol was recovered (n).
- ethoxylated s
- nonionic surfactant s
- the nonionic surfactant preferably additionally has propylene oxide units in the molecule.
- such PO units make up to 25 wt .-%, more preferably up to 20 wt .-% and in particular up to 15 wt .-% of the total molecular weight of the nonionic surfactant from.
- Particularly preferred nonionic surfactants are ethoxylated monohydroxyalkanols or alkylphenols which additionally have polyoxyethylene-polyoxypropylene block copolymer units.
- the alcohol or alkylphenol moiety of such nonionic surfactant molecules preferably constitutes more than 30% by weight, more preferably more than 50% by weight and in particular more than 70% by weight, of the total molecular weight of such nonionic surfactants.
- Preferred rinse aids are characterized in that they contain ethoxylated and propoxylated nonionic surfactants in which the propylene oxide units in the molecule up to 25 wt .-%, preferably up to 20 wt .-% and in particular up to 15 wt .-% of the total molecular weight of nonionic surfactant.
- nonionic surfactants having melting points above room temperature contain from 40 to 70% of a polyoxypropylene / polyoxyethylene / polyoxypropylene block polymer blend containing 75% by weight of a reverse block copolymer of polyoxyethylene and polyoxypropylene with 17 moles of ethylene oxide and 44 moles of propylene oxide and 25% by weight % of a block copolymer of polyoxyethylene and polyoxypropylene initiated with trimethylolpropane and containing 24 moles of ethylene oxide and 99 moles of propylene oxide per mole of trimethylolpropane.
- the mixture according to the invention contains as another preferred nonionic surfactant a compound of the formula (IV) R 4 O [CH 2 CH (CH 3 ) O] x [CH 2 CH 2 O] y [CH 2 CH (OH) R 5 (IV) in which R 4 is a linear or branched aliphatic hydrocarbon radical having 4 to 18 C atoms or mixtures thereof, R 5 denotes a linear or branched hydrocarbon radical having 2 to 26 C atoms or mixtures thereof, and x for values of 0.5 to 1.5 and y stands for a value of at least 15.
- nonionic surfactants are the end-capped poly (oxyalkylated) nonionic surfactants of the formula (V) R 6 O [CH 2 CH (R 8 ) O] z [CH 2 ] k CH (OH) [CH 2 ] j OR 7 (V) in which R 6 and R 7 are linear or branched, saturated or unsaturated, aliphatic or aromatic hydrocarbon radicals having 1 to 30 C atoms, R 8 is hydrogen or a methyl, ethyl, n-propyl, iso-propyl, n is -butyl, 2-butyl or 2-methyl-2-butyl, z is from 1 to 30, k and j are from 1 to 12, preferably from 1 to 5.
- each R 8 in formula (V) may be different.
- R 6 and R 7 are preferably linear or branched, saturated or unsaturated, aliphatic or aromatic hydrocarbon radicals having 6 to 22 carbon atoms, with radicals having 8 to 18 carbon atoms being particularly preferred.
- R 8 hydrogen, methyl or ethyl are particularly preferred.
- Particularly preferred values for z are in the range from 1 to 20, in particular from 6 to 15.
- each R 8 in formula (V) may be different if z ⁇ 2.
- the alkylene oxide unit in the square bracket can be varied.
- the value 3 for z has been selected here by way of example and may well be greater, with the variation range increasing with increasing z value and including, for example, a large number of EO groups combined with a small number of PO groups or vice versa.
- R 6 , R 7 and R 8 are as defined in formula (V) and z is from 1 to 30, preferably from 1 to 20 and in particular from 6 to 18. Particularly preferred are surfactants in which the radicals R 6 and R 7 have 9 to 14 C atoms, R 8 is hydrogen and z assumes values of 6 to 15.
- mixtures according to the invention which contain poly (oxyalkylated) compounds of the formula (V) which end-capped as nonionic surfactants, in which R 6 and R 7 are linear or branched, saturated or unsaturated, aliphatic hydrocarbon radicals having 1 to 30 C atoms, R 8 is hydrogen or a methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl or 2-methyl-2-butyl radical, z is values between 1 and 30, k and j are values from 1 to 12, preferably from 1 to 5, wherein surfactants of the formula (VI) in which z is from 1 to 30, preferably from 1 to 20 and in particular from 6 to 18, are particularly preferred.
- R 6 and R 7 are linear or branched, saturated or unsaturated, aliphatic hydrocarbon radicals having 1 to 30 C atoms
- R 8 is hydrogen or a methyl, ethyl, n-propyl, iso-propyl,
- component (b) to nonionic surfactants which are obtainable under the trade name Pluronic from BASF AG.
- the proportion of component (a) is 5 to 95 wt .-%, preferably 40 to 60 wt .-%.
- An exemplary proportion of component (a) is 50% by weight.
- component (b) is present in an amount of 5 to 95% by weight, preferably 40 to 60% by weight.
- An example is an amount of 50 wt .-%.
- the mixed powders or mixed granules according to the invention can be prepared by mixing both components as a powder and then heating the mixture, in particular to a temperature above the melting or softening point of component (b). This melts component (b) and mixed intimately with component (a). In the subsequent cooling and shaping process, the powder properties such as particle size and bulk density are adjusted.
- the present invention also relates to a process for producing the mixed powders or mixed granules according to the invention by mixing the components (a) and (b) as a powder, heating the mixture and adjusting the powder properties in the subsequent cooling and shaping process. Furthermore, it is possible to granulate the component (a) with the already melted component (b) and then to cool it.
- component (a) can also be stirred into the melt of component (b).
- the subsequent solidification and shaping takes place in accordance with the known processes of melt fabrication, for example by prilling or on cooling belts with, if necessary, downstream steps for adjusting the powder properties, such as grinding and sieving.
- the mixed powders or mixed granules according to the invention can also be prepared by dissolving components (a) and (b) in a solvent and spray-drying the resulting mixture, wherein a granulation step can follow.
- the components (a) and (b) can be dissolved separately, wherein the solutions are subsequently mixed, or a powder mixture of the components can be dissolved in water.
- solvents it is possible to use all those which can dissolve components (a) and (b); preference is given, for example, to using alcohols and / or water, more preferably water.
- the present invention thus also relates to a process for the preparation of the mixed powders or mixed granules according to the invention by dissolving components (a) and (b) in a solvent and spray-drying the resulting mixture, wherein a granulation step and / or a melt granulation step (see above) can follow.
- the present invention also relates to the use of the mixed powders or mixed granules according to the invention for the production of solid detergents and cleaners, in the washing of textiles or in the cleaning of dishes.
- Both components, as mixed powders or mixed granules have an effect in washing and detergents, for example as dishwashing detergents for dishwashing machines.
- the mixed powders or mixed granules can be incorporated into pulverulent detergents and cleaners without these clumping or caking.
- the invention also relates to a solid detergent containing a mixed powder or mixed granules as described above.
- Suitable detergent compositions are known and, for example, in WO 95/29216 and EP-A-0 618 289 described.
- the invention further relates to a solid dishwashing detergent comprising a mixed powder or mixed granules as described above.
- the agents are preferably present in powder or granular form.
- MGDA methylglycinediacetic acid
- PEG 1500 polyethylene glycol having a molecular weight of about 1500 g / mol
- the mixture according to the invention was prepared after melt blending a mixture of MGDA and the polyethylene glycol.
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Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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PL05756996T PL1765967T3 (pl) | 2004-07-02 | 2005-07-01 | Mieszany proszek lub mieszany granulat na bazie mgda |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004032320A DE102004032320A1 (de) | 2004-07-02 | 2004-07-02 | Mischpulver oder Mischgranulat auf Basis von MGDA |
PCT/EP2005/007132 WO2006002954A1 (de) | 2004-07-02 | 2005-07-01 | Mischpulver oder mischgranulat auf basis von mgda |
Publications (2)
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EP1765967A1 EP1765967A1 (de) | 2007-03-28 |
EP1765967B1 true EP1765967B1 (de) | 2018-04-25 |
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EP05756996.4A Active EP1765967B1 (de) | 2004-07-02 | 2005-07-01 | Mischpulver oder mischgranulat auf basis von mgda |
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Country | Link |
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US (1) | US8048838B2 (es) |
EP (1) | EP1765967B1 (es) |
JP (1) | JP2008505236A (es) |
KR (1) | KR101117367B1 (es) |
CN (1) | CN1977036B (es) |
AU (1) | AU2005259456B2 (es) |
BR (1) | BRPI0512778B8 (es) |
CA (1) | CA2572311C (es) |
DE (1) | DE102004032320A1 (es) |
ES (1) | ES2676526T3 (es) |
MX (1) | MXPA06014753A (es) |
NO (1) | NO20070375L (es) |
PL (1) | PL1765967T3 (es) |
TR (1) | TR201810622T4 (es) |
WO (1) | WO2006002954A1 (es) |
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MX2009013320A (es) * | 2007-07-03 | 2010-01-20 | Basf Se | Proceso para producir un solido de flujo libre y estable al almacenamiento que comprende esencialmente acido a-alanina-n, n-diacetico y/o uno o mas derivados de acido a-alanina-n, n-diacetico. |
TR201808032T4 (tr) * | 2008-04-01 | 2018-06-21 | Unilever Nv | Metilglisin diasetik asidin serbest akışlı granüllerinin hazırlanması. |
EP2303961A1 (en) | 2008-07-22 | 2011-04-06 | Akzo Nobel N.V. | Coated particles |
US20120004147A1 (en) | 2008-12-29 | 2012-01-05 | Akzo Nobel N.V. | Coated particles of a chelating agent |
WO2010133617A1 (de) | 2009-05-20 | 2010-11-25 | Basf Se | Verfahren zur herstellung eines sprühpulvers enthaltend ein oder mehrere glycin-n,n-diessigsäure-derivate und verwendung des sprühpulvers zur herstellung von pressagglomeraten |
DE102009038951A1 (de) * | 2009-08-26 | 2011-03-03 | Inprotec Ag | Verfahren zur Herstellung eines kristallinen Feststoffes aus Glycin-N,N-diessigsäure-Derivaten mit hinreichend geringer Hygroskopizität |
MY179613A (en) | 2009-10-30 | 2020-11-11 | Akzo Nobel Chemicals Int Bv | Use of a metal supplement in animal feed |
WO2011076769A1 (en) * | 2009-12-24 | 2011-06-30 | Akzo Nobel Chemicals International B.V. | Coated particles of a glumatic acid n,n-diacetate chelating agent |
EP2380962B1 (en) | 2010-04-23 | 2016-03-30 | The Procter and Gamble Company | Particle |
EP2383329A1 (en) | 2010-04-23 | 2011-11-02 | The Procter & Gamble Company | Particle |
TR201810936T4 (tr) | 2010-04-23 | 2018-08-27 | Industrial Chemicals Group Ltd | Deterjan bileşimi. |
BR112012028249A2 (pt) | 2010-05-21 | 2016-08-02 | Dow Global Technologies Llc | método para produzir um quelante de aminocarboxilato sólido de livre escoamento, método para produzir sal tetrassódico de ácido etilenodiamino-n,n,n',n'-tetra-acético sólido de livre escoamento (na4edta), quelante de aminocarboxilato sólido de livre escoamento, método para preparar um quelante de ácido aminocarboxílico ou sal do mesmo e quelante de ácido aminocarboxílico ou sal do mesmo |
EP2399981A1 (en) | 2010-06-28 | 2011-12-28 | Akzo Nobel Chemicals International B.V. | Particles of a glumatic acid N,N-diacetate chelating agent coated with poly vinyl alcohol PVOH |
WO2012000914A1 (en) | 2010-06-28 | 2012-01-05 | Akzo Nobel Chemicals International B.V. | Particles coated with vinyl alcohol (co) polymer and polysaccharide |
WO2012000915A1 (en) | 2010-06-28 | 2012-01-05 | Akzo Nobel Chemicals International B.V. | Coated particles of a glumatic acid n,n-diacetate chelating agent |
US8754026B2 (en) * | 2010-09-27 | 2014-06-17 | Basf Se | Process for producing granules comprising one or more complexing agent salts |
GB2491619B (en) | 2011-06-09 | 2014-10-01 | Pq Silicas Bv | Builder granules and process for their preparation |
BR112013032880A2 (pt) | 2011-06-29 | 2017-01-24 | Basf Se | mistura, uso da mesma, e, detergente, limpador ou composição de cuidado pessoal ou micronutriente |
EP2584028B1 (en) | 2011-10-19 | 2017-05-10 | The Procter & Gamble Company | Particle |
JP5629404B2 (ja) * | 2012-05-25 | 2014-11-19 | 花王株式会社 | 自動食器洗浄機用洗浄剤組成物 |
JP6140018B2 (ja) * | 2012-07-27 | 2017-05-31 | 花王株式会社 | 食器用洗浄剤組成物 |
GB201214558D0 (en) * | 2012-08-15 | 2012-09-26 | Reckitt Benckiser Nv | Detergent granule |
KR20160120308A (ko) * | 2014-02-13 | 2016-10-17 | 바스프 에스이 | 분말 및 과립, 상기 분말 및 과립의 제조 방법, 및 이의 용도 |
EP3050947A1 (en) * | 2015-02-02 | 2016-08-03 | The Procter and Gamble Company | Detergent pack |
PL3050953T3 (pl) | 2015-02-02 | 2019-07-31 | The Procter And Gamble Company | Kompozycja detergentu |
BR112018077483A2 (pt) | 2016-07-14 | 2019-04-02 | Basf Se | meio de fermentação, métodos para cultivar um microrganismo e para produzir um composto de interesse, solução de oligoelemento para um processo de fermentação, e, uso de um agente quelante. |
EP3585873B1 (en) * | 2017-02-24 | 2021-04-07 | Basf Se | Process for making solid methylglycine diacetate (mgda) alkali metal salt and solid particles |
US20210040418A1 (en) * | 2018-02-23 | 2021-02-11 | Conopco Inc., D/B/A Unilever | Detergent solid composition comprising aminopolycarboxylate and inorganic acid |
GB201814981D0 (en) | 2018-09-14 | 2018-10-31 | Reckitt Benckiser Finish Bv | Granulate |
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EP0618289B1 (en) | 1993-03-30 | 1998-08-19 | The Procter & Gamble Company | High active granular detergents comprising chelants and polymers, and processes for their preparation |
JP3810854B2 (ja) * | 1996-01-22 | 2006-08-16 | 花王株式会社 | 高密度粉末洗剤組成物 |
JPH1053799A (ja) | 1996-08-09 | 1998-02-24 | Kao Corp | 粉末洗剤組成物 |
DE19649681A1 (de) | 1996-11-29 | 1998-06-04 | Basf Ag | Verfahren zur Herstellung eines kristallinen Feststoffes aus Glycin-N,N-diessigsäure-Derivaten mit hinreichend geringer Hygroskopizität |
US6162259A (en) * | 1997-03-25 | 2000-12-19 | The Procter & Gamble Company | Machine dishwashing and laundry compositions |
JP3290382B2 (ja) * | 1997-07-18 | 2002-06-10 | 花王株式会社 | 粉末洗剤組成物 |
DE19807104A1 (de) | 1998-02-20 | 1999-08-26 | Basf Ag | Feste Textilwaschmittel-Formulierung auf Basis von Glycin-N,N-diessigsäure-Derivaten als Buildern mit stark reduziertem Anteil an Silicat-Buildern |
JPH11148093A (ja) * | 1997-11-18 | 1999-06-02 | Kao Corp | 洗剤組成物 |
DE19937345A1 (de) * | 1999-08-11 | 2001-02-15 | Basf Ag | Mischpulver oder Mischgranulat auf Basis von Glycin-N,N-diessigsäure |
-
2004
- 2004-07-02 DE DE102004032320A patent/DE102004032320A1/de not_active Withdrawn
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2005
- 2005-07-01 CA CA2572311A patent/CA2572311C/en not_active Expired - Fee Related
- 2005-07-01 JP JP2007519690A patent/JP2008505236A/ja active Pending
- 2005-07-01 PL PL05756996T patent/PL1765967T3/pl unknown
- 2005-07-01 AU AU2005259456A patent/AU2005259456B2/en not_active Ceased
- 2005-07-01 MX MXPA06014753A patent/MXPA06014753A/es active IP Right Grant
- 2005-07-01 BR BRPI0512778A patent/BRPI0512778B8/pt not_active IP Right Cessation
- 2005-07-01 EP EP05756996.4A patent/EP1765967B1/de active Active
- 2005-07-01 KR KR1020077002508A patent/KR101117367B1/ko active IP Right Grant
- 2005-07-01 TR TR2018/10622T patent/TR201810622T4/tr unknown
- 2005-07-01 CN CN2005800220388A patent/CN1977036B/zh not_active Expired - Fee Related
- 2005-07-01 WO PCT/EP2005/007132 patent/WO2006002954A1/de active Application Filing
- 2005-07-01 ES ES05756996.4T patent/ES2676526T3/es active Active
- 2005-07-01 US US11/571,362 patent/US8048838B2/en not_active Expired - Fee Related
-
2007
- 2007-01-19 NO NO20070375A patent/NO20070375L/no not_active Application Discontinuation
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AU2005259456B2 (en) | 2010-10-28 |
BRPI0512778A (pt) | 2008-04-08 |
CA2572311A1 (en) | 2006-01-12 |
JP2008505236A (ja) | 2008-02-21 |
BRPI0512778B1 (pt) | 2019-04-02 |
KR101117367B1 (ko) | 2012-03-07 |
AU2005259456A1 (en) | 2006-01-12 |
NO20070375L (no) | 2007-01-30 |
CN1977036B (zh) | 2010-06-16 |
WO2006002954A1 (de) | 2006-01-12 |
US20080045430A1 (en) | 2008-02-21 |
MXPA06014753A (es) | 2007-03-23 |
TR201810622T4 (tr) | 2018-08-27 |
DE102004032320A1 (de) | 2006-01-19 |
CA2572311C (en) | 2013-02-26 |
PL1765967T3 (pl) | 2018-09-28 |
KR20070036164A (ko) | 2007-04-02 |
ES2676526T3 (es) | 2018-07-20 |
US8048838B2 (en) | 2011-11-01 |
BRPI0512778B8 (pt) | 2019-11-19 |
CN1977036A (zh) | 2007-06-06 |
EP1765967A1 (de) | 2007-03-28 |
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