US3684723A - Detergent composition - Google Patents
Detergent composition Download PDFInfo
- Publication number
- US3684723A US3684723A US114728A US3684723DA US3684723A US 3684723 A US3684723 A US 3684723A US 114728 A US114728 A US 114728A US 3684723D A US3684723D A US 3684723DA US 3684723 A US3684723 A US 3684723A
- Authority
- US
- United States
- Prior art keywords
- detergent
- foam
- sodium
- soap
- detergent composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003599 detergent Substances 0.000 title abstract description 46
- 239000000203 mixture Substances 0.000 title abstract description 43
- 239000006260 foam Substances 0.000 abstract description 18
- 239000000344 soap Substances 0.000 abstract description 17
- 150000003839 salts Chemical class 0.000 abstract description 8
- 229920000233 poly(alkylene oxides) Polymers 0.000 abstract description 7
- 150000002009 diols Chemical class 0.000 abstract description 5
- 239000007844 bleaching agent Substances 0.000 abstract description 4
- 230000000994 depressogenic effect Effects 0.000 abstract description 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 4
- 239000000194 fatty acid Substances 0.000 abstract description 4
- 229930195729 fatty acid Natural products 0.000 abstract description 4
- 150000004665 fatty acids Chemical class 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 description 18
- 238000005187 foaming Methods 0.000 description 14
- 229920001451 polypropylene glycol Polymers 0.000 description 14
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 9
- 238000005406 washing Methods 0.000 description 8
- -1 alkyl sulphate Chemical compound 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000001276 controlling effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000003760 tallow Substances 0.000 description 5
- 239000004115 Sodium Silicate Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000001768 carboxy methyl cellulose Substances 0.000 description 4
- 229960001922 sodium perborate Drugs 0.000 description 4
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 4
- 229910052911 sodium silicate Inorganic materials 0.000 description 4
- 235000019832 sodium triphosphate Nutrition 0.000 description 4
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 4
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 3
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 3
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 3
- 235000019795 sodium metasilicate Nutrition 0.000 description 3
- 229940048086 sodium pyrophosphate Drugs 0.000 description 3
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 3
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-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
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 239000000271 synthetic detergent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Images
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
- C11D10/00—Compositions of detergents, not provided for by one single preceding group
- C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
- C11D10/042—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on anionic surface-active compounds and soap
-
- 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
- C11D10/00—Compositions of detergents, not provided for by one single preceding group
- C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2068—Ethers
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01S—RADIO DIRECTION-FINDING; RADIO NAVIGATION; DETERMINING DISTANCE OR VELOCITY BY USE OF RADIO WAVES; LOCATING OR PRESENCE-DETECTING BY USE OF THE REFLECTION OR RERADIATION OF RADIO WAVES; ANALOGOUS ARRANGEMENTS USING OTHER WAVES
- G01S1/00—Beacons or beacon systems transmitting signals having a characteristic or characteristics capable of being detected by non-directional receivers and defining directions, positions, or position lines fixed relatively to the beacon transmitters; Receivers co-operating therewith
- G01S1/02—Beacons or beacon systems transmitting signals having a characteristic or characteristics capable of being detected by non-directional receivers and defining directions, positions, or position lines fixed relatively to the beacon transmitters; Receivers co-operating therewith using radio waves
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
-
- 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
- C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
Definitions
- a low-foaming detergent composition containing an anionic detergent, a builder salt and either a C fatty acid soap, a foam-depressant nonionic detergent or a mixture of the soap and the nonionic detergent is improved by the addition of 0.5 to 10% by weight of the composi tion of certain diethers of polyalkylene oxide diols that have a high-temperature foam depressant action.
- the composition can also contain a perborate bleach.
- the invention relates to detergent compositions. More particularly the invention relates to built detergent compositions which are suitable for use in drum-type washing machines as well as in other types of washing machines.
- An ideal detergent composition for this purpose would be one which is low-foaming to very low foaming at high temperatures, i.e. above about 80 C., and has acceptable foaming characteristics at temperatures of up to about 60 C.
- Such a detergent composition would be very suitable for use in drum-type washing machines and in any other type of washing machine, because in spite of its reasonable foaming capacity overfoaming at higher temperatures would be avoided.
- the present invention provides a process of preparing such detergent compositions.
- Foam suppression has also been obtained by the use of so-called mixed-active detergent compositions.
- Such compositions usually contain about 5 to 30% by weight of anionic detergent, such as alkylbenzene snlphonate, alkyl sulphate, fatty alcohol sulphate and the like, as well as builder salt.
- the compositions are called mixed-active since they contain a minor proportion, about 1 to preferably 1 to 5% by weight of the composition, of soap, foam depressant nonionic detergent or a mixture of soap and the nonionic detergent.
- soap is meant an alkali metal or ammonium salt of a C fatty acid.
- Suitable nonionic detergents include the alkylene oxide condensation products or alkyl alcohols, of alkyl phenols and of polyoxypropylene and of other organic hydrophobic compounds.
- Detergent compositions of this type can contain an oxygen-liberating bleaching agent, such as perborate, further silicate and small amounts of optical brighteners and soilsuspending agents, such as carboxymethylcellulose.
- the builder salt can be, for example, a salt of an organic acid such as nitrilotriacetic acid, ethane-l-hydroxy-1,1-diphosphonic acid or a polymeric carboxylic acid, or a salt of a polyphosphate such as sodium tripolyphosphate.
- the weight ratio of anionic detergent to builder salt is between 1:1 and 1:5. By weight of the composition the amount of perborate will be between 0 and 30% and of silicate between 0 and 15%.
- the foam depressant action provided by the soap component in such detergent compositions is stronger according as the soap has a higher content of saturated molecules with at least 20 carbon atoms, such as soap from hardened marine oils or certain vegetable oils, it was established that these soaps still provide a distinct foam-- suppressing effect at low and medium temperatures, which in many respects is undesirable.
- R and R are alkyl groups having a total number of 2 to 30 carbon atoms, R and R are each H or CH and n is variable over a wide range.
- These compounds are thus diethers of polyalkylene oxide diols, the polyalkylene oxide groups of which are naturally not restricted to those consisting of equal alkylene oxides but may also be a mixed polymer of different alkylene oxides.
- the invention provides a detergent composition containing an organic anionic detergent, as well as soap and/ or a nonionic detergent, characterised in that a compound is incorporated which is a diether of a polyalkylene oxide diol of the following general formula:
- the lather controlling effect of the diethers meant by the present invention increases with their molecular weight and reaches an optimum value.
- those compounds are very effective in which n is within the range from 2 to about 40, particularly, if the functional groups in the molecule are properly selected.
- a selection of the suitable functional groups within the specified ranges can be easily made by determining the Hydrophylic-Lipophylic Balance Value of the compound, which value should lie within the range of approximately 1.0 to approximately 4.0.
- Preferred compounds are those of which the polyalkylene oxide group is mainly or completely built up from propylene oxide groups. As such may be men tioned:
- These compounds include those which are already conimercially available as a number of products under the UCON Lubricant trademark. They are usually prepared by reacting an aliphatic alcohol with alkylene oxide(s) in the presence of an alkaline catalyst, followed by etherification of the hydroxyl groups according to any of the various known methods, as described in US. patent specification No. 2,520,612.
- diether compounds according to the invention is not restricted to the washing of laundry, but they may also be advantageously applied in any other 4 cleaning process in which it is desired that at elevated temperature far less foam is produced in the low and medium temperature ranges.
- EXAMPLE 1 The effectiveness of the compounds as high-temperature foam suppressants is shown by the graph in FIG. 1, which was obtained by means of comparative tests made with the following detergent compositions in the dynamic foam meter at concentrations of 5 g./litre and using water having a hardness of 15 DH.
- the foam height of the relevant detergent compositions on the vertical axis is set against the temperature on the horizontal axis.
- a built detergent composition with controlled foaming characteristics consisting, by weight, essentially of from 5 to 30% of an anionic non-soap synthetic detergent; from 1 to 10% of an alkali metal soap of fatty acids having from 8 to 25 carbon atoms; 0 to 10% of a nonionic synthetic detergent; 0 to 30% of sodium perborate; 0* to 15% of sodium silicate; and as a foam controlling agent about 0.5 to 10% of a compound of the general formula (l 1'.
- R and --R are alkyl groups having a total number of 2 to 30 carbon atoms
- --R' is CH
- R" is a radical selected from the group consisting of H and CH and n is a number from 2 to 40, the Hydrophylic- Lipophylic Balance Value of the compound being from 1.0 to 4.0.
- the detergent composition according to claim 2 containing from 1 to 3% of the foam controlling agent.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Radar, Positioning & Navigation (AREA)
- Remote Sensing (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Computer Networks & Wireless Communication (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Detergent Compositions (AREA)
- Labeling Devices (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR971671A FR1416369A (fr) | 1964-04-21 | 1964-04-21 | Dispositif pour reporter automatiquement sur une grande surface des inscriptions définies en coordonnées cartésiennes |
NL6707016A NL6707016A (enrdf_load_stackoverflow) | 1964-04-21 | 1967-05-19 | |
US11472871A | 1971-02-11 | 1971-02-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3684723A true US3684723A (en) | 1972-08-15 |
Family
ID=27247920
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US114728A Expired - Lifetime US3684723A (en) | 1964-04-21 | 1971-02-11 | Detergent composition |
Country Status (8)
Country | Link |
---|---|
US (1) | US3684723A (enrdf_load_stackoverflow) |
BE (1) | BE715378A (enrdf_load_stackoverflow) |
CH (1) | CH503105A (enrdf_load_stackoverflow) |
DE (2) | DE1448703C3 (enrdf_load_stackoverflow) |
DK (1) | DK126125A (enrdf_load_stackoverflow) |
FR (1) | FR1567468A (enrdf_load_stackoverflow) |
GB (1) | GB1221217A (enrdf_load_stackoverflow) |
NL (2) | NL129406C (enrdf_load_stackoverflow) |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3853779A (en) * | 1972-06-06 | 1974-12-10 | Colgate Palmolive Co | Low foaming detergent compositions |
US3966628A (en) * | 1974-08-21 | 1976-06-29 | Westvaco Corporation | Solid cleaning compositions containing C21 dicarboxylic acid |
US3989634A (en) * | 1972-09-14 | 1976-11-02 | Tukovy Prumysl, Oborove Reditelstvi | Detergent containing a tenside with activating power |
US4056481A (en) * | 1974-01-11 | 1977-11-01 | The Procter & Gamble Company | Detergent composition |
US4088598A (en) * | 1974-10-14 | 1978-05-09 | The Procter & Gamble Company | Low sudsing detergent compositions |
US4288341A (en) * | 1978-03-20 | 1981-09-08 | Lever Brothers Company | Detergent product containing deodorant compositions |
US4289641A (en) * | 1978-01-12 | 1981-09-15 | Lever Brothers Company | Detergent product |
US4304679A (en) * | 1978-01-12 | 1981-12-08 | Lever Brothers Company | Detergent product containing deodorant compositions |
US4333844A (en) * | 1979-11-12 | 1982-06-08 | Lever Brothers Company | Detergent compositions |
EP0038101B1 (en) * | 1980-04-09 | 1983-10-19 | Unilever N.V. | Built liquid detergent compositions and method of preparation |
US4430236A (en) | 1981-06-22 | 1984-02-07 | Texize, Division Of Mortonthiokol | Liquid detergent composition containing bleach |
EP0254208A3 (en) * | 1986-07-24 | 1989-07-05 | Henkel Kommanditgesellschaft Auf Aktien | Low foaming and/or foam inhibiting mixtures of tensides and their use |
EP0343503A1 (de) * | 1988-05-27 | 1989-11-29 | Henkel Kommanditgesellschaft auf Aktien | Schaumdrückende Alkylpolyglykolether für Reinigungsmittel |
EP0343504A1 (de) * | 1988-05-27 | 1989-11-29 | Henkel Kommanditgesellschaft auf Aktien | Schaumdrückende Alkylpolyglykolether für Reinigungsmittel |
EP0325909A3 (de) * | 1988-01-11 | 1990-08-22 | Henkel Kommanditgesellschaft auf Aktien | Verwendung endgruppen-verschlossener Fettalkoholethoxylate für schaumarme Reinigungsmittel |
EP0326795A3 (en) * | 1988-01-11 | 1990-08-22 | Henkel Kommanditgesellschaft Auf Aktien | Use of polyglycol ethers as anti-foaming agents in detergents |
US4973423A (en) * | 1987-08-17 | 1990-11-27 | Ecolab Inc. | Foam-inhibiting additives in low-foam cleaning compositions: polyethylene glycol ethers |
US5059342A (en) * | 1989-03-23 | 1991-10-22 | Imperical Chemical Industries Plc | Novel chemical compounds and their use as low foam surfactants and antifoaming agents |
US5484553A (en) * | 1989-09-26 | 1996-01-16 | Ciba-Geigy Corporation | Aqueous, storable wetting agent which is low-foaming in application |
WO2002050223A1 (en) * | 2000-12-15 | 2002-06-27 | Unilever Plc | Detergent compositions with highly ethoxylated nonionic alcohol surfactants |
US6655527B1 (en) * | 2001-07-12 | 2003-12-02 | The United States Of America As Represented By The Secretary Of The Navy | Kit for removing mildew |
US6689735B2 (en) | 2000-12-15 | 2004-02-10 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Detergent compositions |
-
0
- DK DK126125D patent/DK126125A/da unknown
-
1964
- 1964-09-18 DE DE1448703A patent/DE1448703C3/de not_active Expired
-
1965
- 1965-03-12 NL NL6503221A patent/NL129406C/xx active
-
1967
- 1967-05-19 NL NL6707016A patent/NL6707016A/xx unknown
-
1968
- 1968-05-17 BE BE715378D patent/BE715378A/xx unknown
- 1968-05-17 FR FR1567468D patent/FR1567468A/fr not_active Expired
- 1968-05-17 GB GB23610/68A patent/GB1221217A/en not_active Expired
- 1968-05-17 CH CH732668A patent/CH503105A/de not_active IP Right Cessation
- 1968-05-18 DE DE19681767529 patent/DE1767529A1/de active Pending
-
1971
- 1971-02-11 US US114728A patent/US3684723A/en not_active Expired - Lifetime
Cited By (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3853779A (en) * | 1972-06-06 | 1974-12-10 | Colgate Palmolive Co | Low foaming detergent compositions |
US3989634A (en) * | 1972-09-14 | 1976-11-02 | Tukovy Prumysl, Oborove Reditelstvi | Detergent containing a tenside with activating power |
US4056481A (en) * | 1974-01-11 | 1977-11-01 | The Procter & Gamble Company | Detergent composition |
US3966628A (en) * | 1974-08-21 | 1976-06-29 | Westvaco Corporation | Solid cleaning compositions containing C21 dicarboxylic acid |
US4088598A (en) * | 1974-10-14 | 1978-05-09 | The Procter & Gamble Company | Low sudsing detergent compositions |
US4289641A (en) * | 1978-01-12 | 1981-09-15 | Lever Brothers Company | Detergent product |
US4304679A (en) * | 1978-01-12 | 1981-12-08 | Lever Brothers Company | Detergent product containing deodorant compositions |
US4288341A (en) * | 1978-03-20 | 1981-09-08 | Lever Brothers Company | Detergent product containing deodorant compositions |
US4333844A (en) * | 1979-11-12 | 1982-06-08 | Lever Brothers Company | Detergent compositions |
EP0038101B1 (en) * | 1980-04-09 | 1983-10-19 | Unilever N.V. | Built liquid detergent compositions and method of preparation |
US4452717A (en) * | 1980-04-09 | 1984-06-05 | Lever Brothers Company | Built liquid detergent compositions and method of preparation |
US4430236A (en) | 1981-06-22 | 1984-02-07 | Texize, Division Of Mortonthiokol | Liquid detergent composition containing bleach |
EP0254208A3 (en) * | 1986-07-24 | 1989-07-05 | Henkel Kommanditgesellschaft Auf Aktien | Low foaming and/or foam inhibiting mixtures of tensides and their use |
US4973423A (en) * | 1987-08-17 | 1990-11-27 | Ecolab Inc. | Foam-inhibiting additives in low-foam cleaning compositions: polyethylene glycol ethers |
EP0325909A3 (de) * | 1988-01-11 | 1990-08-22 | Henkel Kommanditgesellschaft auf Aktien | Verwendung endgruppen-verschlossener Fettalkoholethoxylate für schaumarme Reinigungsmittel |
US4965019A (en) * | 1988-01-11 | 1990-10-23 | Henkel Kommanditgesellschaft Auf Aktien | Use of selected end-group closed fatty alcohol ethoxylates for low-foam, cold-sprayable cleaning agents |
EP0326795A3 (en) * | 1988-01-11 | 1990-08-22 | Henkel Kommanditgesellschaft Auf Aktien | Use of polyglycol ethers as anti-foaming agents in detergents |
EP0343504A1 (de) * | 1988-05-27 | 1989-11-29 | Henkel Kommanditgesellschaft auf Aktien | Schaumdrückende Alkylpolyglykolether für Reinigungsmittel |
WO1989011525A1 (en) * | 1988-05-27 | 1989-11-30 | Henkel Kommanditgesellschaft Auf Aktien | Anti-froth alkyl polyglycol ethers for detergents (i) |
WO1989011524A1 (en) * | 1988-05-27 | 1989-11-30 | Henkel Kommanditgesellschaft Auf Aktien | Anti-froth alkyl polyglycol ethers for detergents (ii) |
EP0343503A1 (de) * | 1988-05-27 | 1989-11-29 | Henkel Kommanditgesellschaft auf Aktien | Schaumdrückende Alkylpolyglykolether für Reinigungsmittel |
US5059342A (en) * | 1989-03-23 | 1991-10-22 | Imperical Chemical Industries Plc | Novel chemical compounds and their use as low foam surfactants and antifoaming agents |
US5484553A (en) * | 1989-09-26 | 1996-01-16 | Ciba-Geigy Corporation | Aqueous, storable wetting agent which is low-foaming in application |
WO2002050223A1 (en) * | 2000-12-15 | 2002-06-27 | Unilever Plc | Detergent compositions with highly ethoxylated nonionic alcohol surfactants |
US6689735B2 (en) | 2000-12-15 | 2004-02-10 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Detergent compositions |
US20040058835A1 (en) * | 2000-12-15 | 2004-03-25 | Unilever Home & Personal Care, Usa; Division Of Conopco, Inc. | Detergent compositions |
US6720298B2 (en) * | 2000-12-15 | 2004-04-13 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Detergent compositions comprising an ethoxylated alcohol and alkyl ioenzene sulfonate |
US6759380B2 (en) | 2000-12-15 | 2004-07-06 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Detergent compositions |
US6655527B1 (en) * | 2001-07-12 | 2003-12-02 | The United States Of America As Represented By The Secretary Of The Navy | Kit for removing mildew |
Also Published As
Publication number | Publication date |
---|---|
NL6707016A (enrdf_load_stackoverflow) | 1968-11-20 |
DE1767529A1 (de) | 1971-09-09 |
CH503105A (de) | 1971-02-15 |
GB1221217A (en) | 1971-02-03 |
FR1567468A (enrdf_load_stackoverflow) | 1969-05-16 |
DE1448703B2 (de) | 1973-07-05 |
DK126125A (enrdf_load_stackoverflow) | |
DE1448703C3 (de) | 1974-02-07 |
NL129406C (enrdf_load_stackoverflow) | 1970-03-16 |
DE1448703A1 (de) | 1968-10-24 |
NL6503221A (enrdf_load_stackoverflow) | 1965-10-22 |
BE715378A (enrdf_load_stackoverflow) | 1968-11-18 |
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