EP0489768B1 - Antischaummittel für die maschinelle geschirr- und flaschenreinigung - Google Patents
Antischaummittel für die maschinelle geschirr- und flaschenreinigung Download PDFInfo
- Publication number
- EP0489768B1 EP0489768B1 EP90912439A EP90912439A EP0489768B1 EP 0489768 B1 EP0489768 B1 EP 0489768B1 EP 90912439 A EP90912439 A EP 90912439A EP 90912439 A EP90912439 A EP 90912439A EP 0489768 B1 EP0489768 B1 EP 0489768B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- general formula
- weight
- decanol
- hexyl
- mole
- 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
- 238000005406 washing Methods 0.000 title claims abstract 3
- 239000002518 antifoaming agent Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 14
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 14
- 150000002170 ethers Chemical class 0.000 claims abstract description 12
- 239000003513 alkali Substances 0.000 claims abstract description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001298 alcohols Chemical class 0.000 claims description 14
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 12
- 238000004851 dishwashing Methods 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 229920001521 polyalkylene glycol ether Polymers 0.000 claims description 4
- XULHFMYCBKQGEE-MRXNPFEDSA-N 2-Hexyl-1-decanol Natural products CCCCCCCC[C@H](CO)CCCCCC XULHFMYCBKQGEE-MRXNPFEDSA-N 0.000 claims 4
- XULHFMYCBKQGEE-UHFFFAOYSA-N 2-hexyl-1-Decanol Chemical compound CCCCCCCCC(CO)CCCCCC XULHFMYCBKQGEE-UHFFFAOYSA-N 0.000 claims 4
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 claims 4
- LOIMOHMWAXGSLR-UHFFFAOYSA-N 2-hexyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCC LOIMOHMWAXGSLR-UHFFFAOYSA-N 0.000 claims 3
- JYZLSYFPFQTNNO-UHFFFAOYSA-N 2-octyldecan-1-ol Chemical compound CCCCCCCCC(CO)CCCCCCCC JYZLSYFPFQTNNO-UHFFFAOYSA-N 0.000 claims 3
- XMVBHZBLHNOQON-UHFFFAOYSA-N 2-butyl-1-octanol Chemical compound CCCCCCC(CO)CCCC XMVBHZBLHNOQON-UHFFFAOYSA-N 0.000 claims 2
- QNMCWJOEQBZQHB-UHFFFAOYSA-N 2-Hexyl-1-octanol Chemical compound CCCCCCC(CO)CCCCCC QNMCWJOEQBZQHB-UHFFFAOYSA-N 0.000 claims 1
- FAOVRYZLXQUFRR-UHFFFAOYSA-N 2-butyldecan-1-ol Chemical compound CCCCCCCCC(CO)CCCC FAOVRYZLXQUFRR-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000006260 foam Substances 0.000 abstract description 19
- 239000007788 liquid Substances 0.000 abstract description 13
- 125000000217 alkyl group Chemical group 0.000 abstract description 10
- 239000004094 surface-active agent Substances 0.000 abstract description 6
- 239000012141 concentrate Substances 0.000 abstract description 2
- 229940093476 ethylene glycol Drugs 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 229960004063 propylene glycol Drugs 0.000 abstract 1
- 235000013772 propylene glycol Nutrition 0.000 abstract 1
- 239000000047 product Substances 0.000 description 19
- -1 alkylene radical Chemical class 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 12
- 239000012459 cleaning agent Substances 0.000 description 10
- 239000000654 additive Substances 0.000 description 8
- 150000002191 fatty alcohols Chemical class 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- 229940096386 coconut alcohol Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- JBVOQKNLGSOPNZ-UHFFFAOYSA-N 2-propan-2-ylbenzenesulfonic acid Chemical compound CC(C)C1=CC=CC=C1S(O)(=O)=O JBVOQKNLGSOPNZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229940071118 cumenesulfonate Drugs 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102000002322 Egg Proteins Human genes 0.000 description 2
- 108010000912 Egg Proteins Proteins 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000013016 damping Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 1
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical group CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 235000014103 egg white Nutrition 0.000 description 1
- 210000000969 egg white Anatomy 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 238000000034 method 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
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 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
- C11D1/825—Mixtures of compounds all of which are non-ionic
- C11D1/8255—Mixtures of compounds all of which are non-ionic containing a combination of compounds differently alcoxylised or with differently alkylated chains
-
- 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0026—Low foaming or foam regulating compositions
-
- 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
- C11D1/72—Ethers of polyoxyalkylene glycols
- C11D1/721—End blocked ethers
-
- 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
- C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
Definitions
- the invention relates to novel, selected active substance mixtures of alkali-resistant polyalkylene glycol ether compounds which, in the case of their own surfactant action, are distinguished in particular by pronounced foam-suppressing properties when formulated with other known components of foam-like cleaning agents, and their use for machine dishwashing and bottle cleaning in the home and business.
- nonionic surfactants based on polyoxyalkylated alkylphenols and / or fatty alcohols for cleaning hard surfaces is known.
- the high foaming power of these compounds has an unfavorable effect.
- DE-OS 25 56 544 describes cleaning agents, in particular machine dishwashing detergents, which also use end-capped non-ionogenic polyalkylene glycol ether compounds, the class of compounds highlighted there being derived from polyoxyalkylated alcohols having 6 to 22 carbon atoms in the straight-chain or branched alkyl or alkylene radical and are characterized in that they are end-capped with a tert-butyl ether group.
- Compounds of this type are said to be able to be used as foam dampers for nonionic and cationic compounds.
- EP 254 208 A2 describes a special low-foam or foam-suppressing surfactant mixture composed of 20-80% by weight of polyethylene glycol ethers of the general formula R1-O- (CH2CH2O) n -R2, in which R1 is a straight-chain or branched alkyl radical or alkenyl radical with 8 - 18 carbon atoms, R2 is an alkyl radical with 4 to 8 carbon atoms and n is a number from 3 to 7, 10 to 40 wt .-% alkyl polyalkylene glycol mixed ether of the general formula R3-O- (CH2CH2O) x - (CH2-CH (CH3) O) y -H, in which R3 is a straight-chain or branched alkyl radical having 8 to 18 carbon atoms, x is a number from 1 to 3 and y is a number of 3 to 6, and 0 to 40% by weight of alkyl (poly) propylene glycol ether of the
- EP 124 815 A3 the use of polyglycol ethers of the formula R1-O- (CH2CH2O) n -R2, in which R1 is a straight-chain or branched alkyl or alkenyl radical with 8 to 18 carbon atoms, R2 is an alkyl radical with 4 to 8 carbon atoms and n is a number from 7 to 12, recommended as foam-suppressing additives for low-foam cleaning agents.
- Such compounds can optionally also be part of the active ingredient combination according to the invention.
- EP 326 795 A2 the use of polyethylene glycol ether of the general formula (I) R1O- (CH2CH2O) n -R2, in which R1 is a straight-chain or branched alkyl or alkenyl radical having 20 to 28 C atoms, R2 is an alkyl radical having 4 up to 8 carbon atoms and n are a number from 6 to 20, described as foam-suppressing additives for low-foam cleaning agents. These compounds are very effective, but sometimes insoluble.
- the teaching of the present invention is based on the object of enabling further improvements of such cleaning and / or rinsing agents for hard surfaces, in particular for the mechanical cleaning of glass, dishes, bottles and the like.
- the invention intends to provide mixtures of substances which, on the one hand, are themselves surfactant-like, but in particular are suitable for use as strongly foam-suppressing additives in low-foam alkali-resistant detergent mixtures of the type concerned here.
- the active substance combinations according to the invention should be able to be used in particular in combination with other customary nonionic, cationic or anionic surface-active substances, builders and other additives or auxiliaries in the dishwashing and cleaning agent formulations of the subject area concerned.
- An essential component for the active ingredient mixtures of the invention are the mixed ethers of the general formula (III) which, as a rule, can even make up the main part of the active ingredient mixture described according to the invention and used for the stated purpose.
- These components known per se are substantially improved by the addition of the active ingredient components to (1) and (2) provided according to the invention. This improvement affects both the ability to inhibit or limit foam and that Formulation of the active ingredient mixture into clearly soluble aqueous concentrates.
- the invention provides for the mixture components of the general formula (I) to (1) on the one hand and the mixture components of the general formula (II) to (2) on the other hand in combination with one another together with the compounds of the general formula (III) - mixture component to ( 3) - and the mixture components (4) additionally used if desired.
- these mixture components to (1) and (2) can produce effective effects in the sense of the desired improvements.
- up to about 20% by weight based on the total mixture of the active compounds according to the invention, of the components to (1) and (2) or even with amounts of up to about 10% by weight of these additives according to the invention, a significant reduction foam formation on the one hand and improvement of the aqueous formulability of the active ingredients on the other hand can be achieved.
- alcohols of this type are formed by the condensation of fatty alcohols with a lower carbon number in the presence of alkali, e.g. As potassium hydroxide or potassium alcoholate. The reaction takes place, for example, at temperatures from 200 to 300 ° C. and leads to branched Guerbet alcohols which have branching in the 2-position to the hydroxyl group.
- alkali e.g. As potassium hydroxide or potassium alcoholate.
- the reaction takes place, for example, at temperatures from 200 to 300 ° C. and leads to branched Guerbet alcohols which have branching in the 2-position to the hydroxyl group.
- the invention predominantly or preferably exclusively uses straight-chain fatty alcohols for the preparation of the 2-branched Guerbet alcohols and ultimately for the synthesis of the compounds of the general formula (I).
- Fatty alcohols of natural origin are known to have at least largely predominantly even chain lengths, so that their 2-branched Guerbet alcohol with 18 C atoms cannot be obtained as a uniform condensation product of only one selected fatty alcohol via their dimerization.
- the necessary dimerization of a mixture of the two fatty alcohols with 8 and 10 C atoms leads to the isomer mixture of the 18 C Guerbet alcohol from 2-hexyldodecanol-1 and 2-octyldecanol-1.
- the condensation products of the two alcohols used arise with themselves, i. that is, the 2-hexyldecanol-1 from the octanol used and the 2-octyldodecanol-1 from the decanol used.
- Analogous considerations apply to Guerbet alcohol with 14 carbon atoms.
- the end group-capped fatty alcohol polyglycol ethers of the formula (I) are prepared in accordance with the specifications of DE-OS 33 15 951.
- the fatty alcohols of higher carbon number described above are advantageously reacted with ethylene oxide in a molar ratio of 1: 5 to 1: 9 and then etherified the hydroxyl groups present in the reaction product obtained.
- the reaction with ethylene oxide takes place under the known acoxylation conditions, preferably in the presence of suitable alkaline catalysts.
- the etherification of the free hydroxyl groups is preferably carried out under the known conditions of Williamson's ether synthesis using straight-chain or branched C4- to C8-alkyl halides.
- n-butyl radical for the radical R2 from the general formula (I) is of particular importance in the course of the inventive action.
- examples of such a final etherification are accordingly n-butyl halides such as n-butyl chloride.
- the invention is not limited to this. Further examples are amyl halides, hexyl halides and the higher alkyl halides in the range mentioned. It may be expedient to use alkyl halide and alkali in a stoichiometric excess, for example from 10 to 50%, over the hydroxyl groups to be etherified.
- the compounds of the general formula (II) which are not end-capped are prepared in a manner known per se by reacting the selected Guerbet alcohols with ethylene oxide in a molar ratio of 1: 2 to 1: 5.
- the compounds of the general formula (III) - mixture components to (3) - are obtained in a manner known per se - by reacting the selected linear or branched alkanols ROH with ethylene oxide and propylene oxide - in particular 1,2-propylene oxide - in the stated molar ratios.
- the preparation of the if necessary the mixture components of the general formula (IV) used are analogous to the information on the preparation of the end group-sealed mixture components of the general formula (I).
- the active compound mixtures according to the invention are suitable both as a foam-suppressing additive to typical cleaning agent mixtures, in particular low-foam mixtures of the type mentioned, in order to further reduce their tendency to foam, and also for the formulation of rinse aids.
- low-foam surfactants can be used in a manner known per se, the foam formation of which is further suppressed by the active ingredient systems according to the invention.
- the content of the active ingredient mixtures of (1) to (4) in the detergents and cleaning agents can vary within wide limits. It is essential that the polyglycol ether mixtures give effective effects even in low concentrations. In a preferred embodiment, they are added to the cleaning agents in such amounts that their concentration in the ready-to-use solutions is approximately in the range from 50 to 500 ppm. However, the invention is not restricted to this; in particular, far higher amounts of the active compound mixtures according to the invention can be used.
- a whisked whole egg yolk and egg white
- this liquid is heated to 60 o C in a double-walled 2000 ml measuring cylinder.
- this solution is sucked from the bottom of the measuring cylinder with a glass tube.
- the liquid is returned to the measuring cylinder via a second tube, the lower end of which ends at the height of the upper edge of the measuring cylinder.
- the liquid is at a circulation rate of 4 l / min. pumped over and falls back into the measuring cylinder. By pumping around this liquid can be foamed up to 2000 ml.
- the examined products are the following:
- Product B has a better anti-foaming effect than products A, C and D.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3928600A DE3928600A1 (de) | 1989-08-30 | 1989-08-30 | Schaumdaempfende mehrstoffgemische mit tensidcharakter fuer die maschinelle geschirr- und flaschenreinigung |
| DE3928600 | 1989-08-30 | ||
| PCT/EP1990/001384 WO1991003540A1 (de) | 1989-08-30 | 1990-08-21 | Antischaummittel für die maschinelle geschirr- und flaschenreinigung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0489768A1 EP0489768A1 (de) | 1992-06-17 |
| EP0489768B1 true EP0489768B1 (de) | 1995-06-14 |
Family
ID=6388136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90912439A Expired - Lifetime EP0489768B1 (de) | 1989-08-30 | 1990-08-21 | Antischaummittel für die maschinelle geschirr- und flaschenreinigung |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0489768B1 (es) |
| AT (1) | ATE123800T1 (es) |
| DE (2) | DE3928600A1 (es) |
| DK (1) | DK0489768T3 (es) |
| ES (1) | ES2073032T3 (es) |
| PT (1) | PT95121B (es) |
| WO (1) | WO1991003540A1 (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0600847B2 (en) * | 1992-11-26 | 2001-10-31 | The Procter & Gamble Company | Cleaning compositions with combined highly hydrophilic and highly hydrophobic nonionic surfactants |
| EP0598973A1 (en) * | 1992-11-26 | 1994-06-01 | The Procter & Gamble Company | Multi-purpose liquid cleaning composition |
| DE4323252C2 (de) * | 1993-07-12 | 1995-09-14 | Henkel Kgaa | Klarspüler für die maschinelle Reinigung harter Oberflächen |
| DE4327327A1 (de) * | 1993-08-13 | 1995-02-16 | Henkel Kgaa | Detergensgemische |
| DE4342214C1 (de) * | 1993-12-10 | 1995-05-18 | Henkel Kgaa | Nichtionische Detergensgemische |
| DE4431158C2 (de) * | 1994-09-01 | 1999-10-21 | Henkel Kgaa | Methyl-endgruppenverschlossene Alkyl- und/oder Alkenylpolyglycolether |
| DE4439086C2 (de) * | 1994-11-02 | 1997-11-27 | Henkel Kgaa | Verfahren zur Herstellung von endgruppenverschlossenen nichtionischen Tensiden |
| DE19500842C2 (de) * | 1995-01-13 | 1996-12-19 | Henkel Kgaa | Verfahren zur Herstellung von endgruppenverschlossenen nichtionischen Tensiden |
| DE19738866A1 (de) | 1997-09-05 | 1999-03-11 | Henkel Kgaa | Schaumarme Tensidmischungen mit Hydroxymischethern |
| DE19851453A1 (de) | 1998-11-09 | 2000-05-11 | Cognis Deutschland Gmbh | Klarspüler für das maschinelle Geschirrspülen |
| DE19856727A1 (de) | 1998-12-09 | 2000-06-15 | Cognis Deutschland Gmbh | Allzweckreiniger |
| DE19920559A1 (de) * | 1999-05-05 | 2000-11-16 | Cognis Deutschland Gmbh | Verfahren zur Herstellung von alkyl-endgruppenverschlossenen Alkyl- und/oder Alkenylethern |
| CN102656209A (zh) | 2009-12-09 | 2012-09-05 | 陶氏环球技术有限责任公司 | 仲羟基脂肪酸及其衍生物的聚醚衍生物 |
| CN103642033A (zh) * | 2013-11-18 | 2014-03-19 | 南京理工大学 | 一种格尔伯特醇非离子表面活性剂 |
| US9982220B2 (en) | 2015-05-19 | 2018-05-29 | Ecolab Usa Inc. | Efficient surfactant system on plastic and all types of ware |
| WO2017198438A1 (en) | 2016-05-17 | 2017-11-23 | Unilever Plc | Liquid laundry detergent compositions |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0124815A2 (de) * | 1983-05-02 | 1984-11-14 | Henkel Kommanditgesellschaft auf Aktien | Verwendung von Polyglykolethern als schaumdrückende Zusätze in schaumarmen Reinigungsmitteln |
| EP0326795A2 (de) * | 1988-01-11 | 1989-08-09 | Henkel Kommanditgesellschaft auf Aktien | Verwendung von Polyglykolethern als schaumvermindernde Zusätze für Reinigungsmittel |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2026494T3 (es) | 1986-07-24 | 1992-05-01 | Henkel Kommanditgesellschaft Auf Aktien | Mezclas de tensioactivos pobres en espuma y/o reductoras de espuma y su empleo. |
| CH676994A5 (es) * | 1987-05-06 | 1991-03-28 | Sandoz Ag |
-
1989
- 1989-08-30 DE DE3928600A patent/DE3928600A1/de not_active Withdrawn
-
1990
- 1990-08-21 DK DK90912439.8T patent/DK0489768T3/da active
- 1990-08-21 AT AT90912439T patent/ATE123800T1/de not_active IP Right Cessation
- 1990-08-21 DE DE59009251T patent/DE59009251D1/de not_active Expired - Lifetime
- 1990-08-21 EP EP90912439A patent/EP0489768B1/de not_active Expired - Lifetime
- 1990-08-21 WO PCT/EP1990/001384 patent/WO1991003540A1/de active IP Right Grant
- 1990-08-21 ES ES90912439T patent/ES2073032T3/es not_active Expired - Lifetime
- 1990-08-28 PT PT95121A patent/PT95121B/pt not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0124815A2 (de) * | 1983-05-02 | 1984-11-14 | Henkel Kommanditgesellschaft auf Aktien | Verwendung von Polyglykolethern als schaumdrückende Zusätze in schaumarmen Reinigungsmitteln |
| EP0326795A2 (de) * | 1988-01-11 | 1989-08-09 | Henkel Kommanditgesellschaft auf Aktien | Verwendung von Polyglykolethern als schaumvermindernde Zusätze für Reinigungsmittel |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0489768A1 (de) | 1992-06-17 |
| PT95121B (pt) | 1997-05-28 |
| PT95121A (pt) | 1991-05-22 |
| ES2073032T3 (es) | 1995-08-01 |
| DK0489768T3 (da) | 1995-10-30 |
| WO1991003540A1 (de) | 1991-03-21 |
| DE59009251D1 (de) | 1995-07-20 |
| DE3928600A1 (de) | 1991-03-07 |
| ATE123800T1 (de) | 1995-06-15 |
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