EP0641379A1 - Procede de stabilisation de couleur de tensioactifs - Google Patents
Procede de stabilisation de couleur de tensioactifsInfo
- Publication number
- EP0641379A1 EP0641379A1 EP93912702A EP93912702A EP0641379A1 EP 0641379 A1 EP0641379 A1 EP 0641379A1 EP 93912702 A EP93912702 A EP 93912702A EP 93912702 A EP93912702 A EP 93912702A EP 0641379 A1 EP0641379 A1 EP 0641379A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- sulfates
- surfactants
- ether
- alkyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims description 19
- 230000000087 stabilizing effect Effects 0.000 title claims description 6
- 239000003112 inhibitor Substances 0.000 claims abstract description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- -1 olefin sulfates Chemical class 0.000 claims description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 8
- 235000003704 aspartic acid Nutrition 0.000 claims description 7
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 230000006641 stabilisation Effects 0.000 claims description 4
- 238000011105 stabilization Methods 0.000 claims description 4
- ODAKQJVOEZMLOD-UHFFFAOYSA-N 3-[bis(carboxymethyl)amino]-2-hydroxypropanoic acid Chemical compound OC(=O)C(O)CN(CC(O)=O)CC(O)=O ODAKQJVOEZMLOD-UHFFFAOYSA-N 0.000 claims description 3
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 3
- 239000002280 amphoteric surfactant Substances 0.000 claims description 3
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002888 zwitterionic surfactant Substances 0.000 claims description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 2
- RRBZUCWNYQUCTR-UHFFFAOYSA-N 2-(aminoazaniumyl)acetate Chemical class NNCC(O)=O RRBZUCWNYQUCTR-UHFFFAOYSA-N 0.000 claims description 2
- BCFOOQRXUXKJCL-UHFFFAOYSA-N 4-amino-4-oxo-2-sulfobutanoic acid Chemical class NC(=O)CC(C(O)=O)S(O)(=O)=O BCFOOQRXUXKJCL-UHFFFAOYSA-N 0.000 claims description 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical class CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 2
- 229930045534 Me ester-Cyclohexaneundecanoic acid Natural products 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 150000002191 fatty alcohols Chemical class 0.000 claims description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 229920000136 polysorbate Polymers 0.000 claims description 2
- 229940068965 polysorbates Drugs 0.000 claims description 2
- 150000003871 sulfonates Chemical class 0.000 claims description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims 1
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 14
- 229910052742 iron Inorganic materials 0.000 description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 238000002845 discoloration Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- BTLHODXEDLCLAD-VKHMYHEASA-N (2s)-2-(carboxymethylamino)butanedioic acid Chemical compound OC(=O)CN[C@H](C(O)=O)CC(O)=O BTLHODXEDLCLAD-VKHMYHEASA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000004851 dishwashing Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- DCEMCPAKSGRHCN-UHFFFAOYSA-N oxirane-2,3-dicarboxylic acid Chemical compound OC(=O)C1OC1C(O)=O DCEMCPAKSGRHCN-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- JYXGIOKAKDAARW-UHFFFAOYSA-N N-(2-hydroxyethyl)iminodiacetic acid Chemical compound OCCN(CC(O)=O)CC(O)=O JYXGIOKAKDAARW-UHFFFAOYSA-N 0.000 description 1
- IBYNMHGLXCSFEW-UHFFFAOYSA-N OOO.OS(O)(=O)=O Chemical class OOO.OS(O)(=O)=O IBYNMHGLXCSFEW-UHFFFAOYSA-N 0.000 description 1
- OBOXTJCIIVUZEN-UHFFFAOYSA-N [C].[O] Chemical compound [C].[O] OBOXTJCIIVUZEN-UHFFFAOYSA-N 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000012216 screening Methods 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
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/51—Chelating agents
Definitions
- the invention relates to a method for color stabilization of surfactants, in which selected inhibitors are added.
- Surfactants such as fatty alcohol ether sulfates are used, among other things, for the production of washing. Dishwashing and cleaning agents as well as hair and body care products. If these products come onto the market as raw materials, they are usually adjusted to a pH of 7 to 9 by adding alkalis before further use. As a result of the manufacturing process, e.g. B. the sulfonation with chlorosulfonic acid, which always contains traces of iron, as well as contamination during transport and storage, such surfactants always have a low iron ion content. Since these act as autoxidation promoters, iron contamination leads to the formation of undesirable and often color-causing oxidation products. At higher pH values, a fine colloidal precipitation of iron (III) - come hydroxide, which makes further processing of the surfactants into final formulations difficult, if not impossible.
- the object of the invention was therefore to develop new stabilizers for surfactants which are free from the disadvantages described.
- the invention relates to a method for stabilizing surfactants, in which inhibitors of the formula (I) are added,
- Rl and R3 are independently hydrogen or one
- inhibitors mentioned stabilizes anionic, nonionic and / or amphoteric or zwitterioic surfactants reliably and permanently against discoloration.
- a particular advantage of the inhibitors to be used according to the invention is their excellent biodegradability.
- Suitable surfactants are aqueous, anionic, nonionic and / or amphoteric or zwitterionic surfactants, which can be in the form of solutions or pastes.
- anionic surfactants which can be stabilized in the sense of the process according to the invention are alkylbenzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, o-methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, hydroxyl ether sulfates, glycerol ether sulfates ) sulfates, fatty acid amide (ether) sulfates, sulfosuccinates, Sulfosuccinamates, sulfotriglycerides, ether carboxylic acids, alkyl oligoglucoside sulfates and alkyl (ether) phosphates.
- nonionic surfactants which can be stabilized by the process according to the invention are fatty alcohol ethoxylates, polyol fatty acid esters, alkyl oligoglycosides, sorbitan esters and polysorbates, while amphoteric or zwitterionic surfactants are, for example, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobins.
- the surfactants can have a solids content of 5 to 85, preferably 25 to 70% by weight, based on the products.
- inhibitors which are suitable for stabilizing surfactants in the sense of the process according to the invention are N- (carboxymethyl) aminosuccinic acid, N- (1,2-dicarboxyethyl) aspartic acid, nitrilodiacetic acid-3-propionic acid, glucamine-N, N-diacetic acid, hydroxyethyliminodi- H 0204/0205 - 5 -
- acetic acid and in particular N- (1,2-dicarboxyethyl) glycine, N- (1,2-dicarboxy-2-hydroxyethyl) aspartic acid, isoserine-N, N-diacetic acid and nitrilotriacetic acid.
- N- (1,2-dicarboxy-2-hydroxyethyl) aspartic acid can be prepared by ring opening epoxysuccinic acid with aspartic acid or nitrilodiacetic acid-3-propionic acid by reacting iminodiacetic acid with acrylic acid [DE-A-40 24 552, Henkel] .
- the inhibitors can be added to the surfactants in amounts of 10 to 1500, preferably 100 to 500 ppm, based on the solids content of the products. Furthermore, it has proven to be particularly advantageous to adjust the surfactants to a pH of 7 to 11, preferably 7.5 to 9.
- the surfactants obtainable by the process according to the invention are stabilized against discoloration and are suitable for the production of detergents, dishwashing detergents and cleaning agents and products for hair and body care, in which they are present in amounts of 1 to 90, preferably 5 to 50 % By weight, based on the composition, may be present.
- NTA Nitrilotriacetic acid
- Ci2 / 14- ⁇ ° kosfettalkohol-2EO ether sulfate Na salt (Texapon ( R ), 26.5 wt .-% in water, Henkel KGaA, Dusseldorf, FRG) was with a content of 10 ppm Iron (in the form of iron (III) chloride) and optionally 150 ppm inhibitor - in each case based on the solids content of the products - added.
- the ether sulfate known from Examples 1 to 9 was doped with 40 ppm iron and 150 ppm inhibitor - in each case based on the solids content of the products - and over a period of 21 d at pH values in the range from 8 to 11 as previously described stored.
- the color numbers are shown in Tab. 3.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
On peut stabiliser les tensioactifs, pour éviter qu'ils ne se décolorent, en leur ajoutant un inhibiteur de la formule (I), dans laquelle R1 et R3 représentent hydrogène ou un groupe carboxyle, indépendamment l'un de l'autre, R2 représente hydrogène ou un groupe CH¿2?COOH, R?4¿ représente un groupe carboxyle, un groupe hydroxyle, un groupe CH(OH)COOH ou un groupe (CHOH)¿5?H et n et m valent, indépendamment l'un de l'autre, 0 ou 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4216363A DE4216363A1 (de) | 1992-05-18 | 1992-05-18 | Verfahren zur Farbstabilisierung von Tensiden |
| DE4216363 | 1992-05-18 | ||
| PCT/EP1993/001149 WO1993023515A1 (fr) | 1992-05-18 | 1993-05-11 | Procede de stabilisation de couleur de tensioactifs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0641379A1 true EP0641379A1 (fr) | 1995-03-08 |
Family
ID=6459139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP93912702A Ceased EP0641379A1 (fr) | 1992-05-18 | 1993-05-11 | Procede de stabilisation de couleur de tensioactifs |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0641379A1 (fr) |
| JP (1) | JPH07506762A (fr) |
| DE (1) | DE4216363A1 (fr) |
| WO (1) | WO1993023515A1 (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5840670A (en) * | 1996-01-30 | 1998-11-24 | Colgate-Palmolive Co. | Composition |
| US5843876A (en) * | 1996-01-30 | 1998-12-01 | Colgate-Palmolive Co. | Composition |
| EP0877596B1 (fr) * | 1996-01-30 | 2001-07-04 | Colgate-Palmolive Company | Composition de nettoyage comprenant un ou plusieurs stabilisants des couleurs et un ou plusieurs tensioactifs |
| ZA97698B (en) * | 1996-01-30 | 1998-07-28 | Colgate Palmolive Co | Composition |
| DE69811786T2 (de) * | 1997-07-16 | 2003-10-23 | Nagase Chemtex Corp., Osaka | Verwendung von Chelat bildenden Zusammensetzungen zum Reinigen |
| JP6462338B2 (ja) * | 2013-11-29 | 2019-01-30 | 川研ファインケミカル株式会社 | アミノ糖誘導体を含有する化粧料 |
| DE102013225591A1 (de) * | 2013-12-11 | 2015-06-11 | Henkel Ag & Co. Kgaa | Maschinelles Geschirrspülmittel enthaltend N-basierte Komplexbildner |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1565807A (en) * | 1975-12-18 | 1980-04-23 | Uilever Ltd | Process and compositions for cleaning fabrics |
| US4560492A (en) * | 1984-11-02 | 1985-12-24 | The Procter & Gamble Company | Laundry detergent composition with enhanced stain removal |
| US4769168A (en) * | 1985-08-05 | 1988-09-06 | Colgate-Palmolive Company | Low phosphate or phosphate free nonaqueous liquid nonionic laundry detergent composition and method of use |
-
1992
- 1992-05-18 DE DE4216363A patent/DE4216363A1/de not_active Withdrawn
-
1993
- 1993-05-11 JP JP5519859A patent/JPH07506762A/ja active Pending
- 1993-05-11 WO PCT/EP1993/001149 patent/WO1993023515A1/fr not_active Ceased
- 1993-05-11 EP EP93912702A patent/EP0641379A1/fr not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9323515A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07506762A (ja) | 1995-07-27 |
| WO1993023515A1 (fr) | 1993-11-25 |
| DE4216363A1 (de) | 1993-11-25 |
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