WO1994011331A1 - Use of alkoxylate of 2-propyl heptanol - Google Patents

Use of alkoxylate of 2-propyl heptanol Download PDF

Info

Publication number
WO1994011331A1
WO1994011331A1 PCT/SE1993/000966 SE9300966W WO9411331A1 WO 1994011331 A1 WO1994011331 A1 WO 1994011331A1 SE 9300966 W SE9300966 W SE 9300966W WO 9411331 A1 WO9411331 A1 WO 9411331A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkoxylate
compounds
carbon atoms
foaming
propyl heptanol
Prior art date
Application number
PCT/SE1993/000966
Other languages
French (fr)
Inventor
Lennart Dahlgren
Karin BERGSTRÖM
Original Assignee
Berol Nobel Ab
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Berol Nobel Ab filed Critical Berol Nobel Ab
Priority to JP51200594A priority Critical patent/JP4104650B2/en
Priority to EP94901106A priority patent/EP0669906B1/en
Priority to US08/436,268 priority patent/US5608118A/en
Priority to CA002148705A priority patent/CA2148705C/en
Priority to DE69310925T priority patent/DE69310925T2/en
Publication of WO1994011331A1 publication Critical patent/WO1994011331A1/en
Priority to NO951962A priority patent/NO303220B1/en
Priority to FI952430A priority patent/FI107913B/en

Links

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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0026—Low foaming or foam regulating compositions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/10—Saturated ethers of polyhydroxy compounds
    • C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
    • 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

  • the present invention relates to the use of an al oxylate of 2-propyl heptanol in compositions for cleaning hard surfaces.
  • the alkoxylate shows low foam ⁇ ing compared with similar compounds having a hydrophobic group of the same size.
  • the alkoxylate may advantageously be used as a surface-active component in detergent compo ⁇ sitions. It has long been known to alkoxylate alcohols for obtaining non-ionic surface-active compounds. These com ⁇ pounds have been used e.g. in detergent compositions because of their wetting and dispersing properties. In a number of applications, alkoxylates of C 0 ,, alcohols have however been found to be too high-foaming and/or not to have the desired detergent power.
  • an alkoxylate based on 2-propyl heptanol is suitable for use as a detergent in compositions for cleaning hard surfaces, since it has good detergent and wetting properties as well as low foaming as compared with other alcohols having substantially the same chain length.
  • the alkoxylate also has a desirable thickening effect.
  • the alkoxylate is easily degradable and has a surprisingly low biotoxicity. In tests, no skin-irritant effect has been noted.
  • the alkoxylate for use according to the invention can be illustrated by the formula C 5 H 11 CH(C 3 H 7 )CH 2 0(A) n H (I) wherein A is an alkyleneoxy group having 2-4 carbon atoms and n is 2-16, preferably 3-12.
  • A is an alkyleneoxy group having 2-4 carbon atoms and n is 2-16, preferably 3-12.
  • 50-100% of all _ alkyleneoxy groups are ethyleneoxy groups. In those cases where different alkyleneoxy groups are present in the same compound, they may be added randomly or in block.
  • the alkoxylate is an ethoxylate having 3-7, preferably 4-6 ethyleneoxy groups. - 0
  • ethylene oxide can be added in a first step and thereafter alkylene oxide having 3-4 carbon atoms.
  • B is an alkyleneoxy group having 3-4 carbon atoms
  • p is 1-10 and r is 1-6.
  • p is 2-8 and r is 1-4.
  • the alkoxylates for use according to the invention described above can be prepared by adding in a conven ⁇ tional manner in the presence of a conventional alkali catalyst, such as potassium hydroxide or sodium hydroxide, the above-mentioned amounts of alkylene oxide to 2-propyl heptanol, which is a so-called Guebert alcohol.
  • a conventional alkali catalyst such as potassium hydroxide or sodium hydroxide
  • the addition of ethylene oxide is performed using a conventional catalyst which gives a narrower distribution of added ethylene oxide than any alkali catalyst, such as NaOH or KOH.
  • any alkali catalyst such as NaOH or KOH.
  • Examples of conventional catalysts giving a narrow distribution of added alkylene oxide are Ca ⁇ OH)-, Ba(OH)...,
  • the reaction is preferably con ⁇ ducted in the absence of free water to reduce the amount of by-products and usually at a temperature of 70-180°C.
  • the alkoxylate, especially ethoxylate and alkoxylate of formula II, is suitably included in compositions for cleaning hard surfaces, e.g. for degreasing or dishwash ⁇ ing. Especially good results have been obtained when degreasing lacquered or unlacquered metal surfaces.
  • the compositions may also con ⁇ tain other detergents, such as anionic surface-active com ⁇ pounds.
  • compositions may contain solutising additives, complexing agents and/or pH-ad usting agents, enzymes, other surface-active compo ⁇ nents, bactericides and perfumes.
  • the compositions are usually aqueous and in the form of emulsions, microemul- sions or solutions.
  • Example 1 Alkoxylates according to the invention are prepared by alkoxylating 2-propyl ethanol with the amounts of alky ⁇ lene oxide appearing from the Table below in the presence of potassium hydroxide or Ca(0H)_ as catalyst. The result ⁇ ing products were analysed and structurally determined by gas chromatography and mass spectrometry. The turbidity points were measured in water or monobutylether diethylene glycol. The following results were obtained.
  • EO ethylene oxide
  • PO propylene oxide
  • BDG monobutylether diethylene glycol 1
  • microtoxicity which is a measure of the aquatic toxicity, was determined for the compounds below as the water concentration of the compounds at which the ability of luminescent bacteria to emit light for 5 min is reduced by 50%. The following results were obtained.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Saccharide Compounds (AREA)
  • Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
  • Polyethers (AREA)

Abstract

The invention relates to the use of an alkoxylate having the general formula (I): C5H11CH(C3H7)CH2O(A)nH, wherein A is an alkyleneoxy group having 2-4 carbon atoms and n is 2-16, preferably 3-12, in detergent compositions for degreasing hard surfaces.

Description

USE OF ALKOXYLATE OF 2-PROPYL HEPTANOL
The present invention relates to the use of an al oxylate of 2-propyl heptanol in compositions for cleaning hard surfaces. The alkoxylate shows low foam¬ ing compared with similar compounds having a hydrophobic group of the same size. The alkoxylate may advantageously be used as a surface-active component in detergent compo¬ sitions. It has long been known to alkoxylate alcohols for obtaining non-ionic surface-active compounds. These com¬ pounds have been used e.g. in detergent compositions because of their wetting and dispersing properties. In a number of applications, alkoxylates of C0 ,, alcohols have however been found to be too high-foaming and/or not to have the desired detergent power. For example, ethoxy- lates based on branched C„ alcohols often exhibit accept¬ able foaming but too low a detergent power, whereas ethoxylates based on straight or branched alcohols having a larger hydrocarbon chain often show an acceptable sur¬ face activity but too high foaming. Thus, there is a need for new alkylene oxide adducts with an improved ratio of foaming to detergent power.
It has now been found that an alkoxylate based on 2-propyl heptanol is suitable for use as a detergent in compositions for cleaning hard surfaces, since it has good detergent and wetting properties as well as low foaming as compared with other alcohols having substantially the same chain length. In formulations, the alkoxylate also has a desirable thickening effect. In addition, it has been found that the alkoxylate is easily degradable and has a surprisingly low biotoxicity. In tests, no skin-irritant effect has been noted.
The alkoxylate for use according to the invention can be illustrated by the formula C5H11CH(C3H7)CH20(A)nH (I) wherein A is an alkyleneoxy group having 2-4 carbon atoms and n is 2-16, preferably 3-12. Preferably, 50-100% of all _ alkyleneoxy groups are ethyleneoxy groups. In those cases where different alkyleneoxy groups are present in the same compound, they may be added randomly or in block.
Generally, the alkoxylate is an ethoxylate having 3-7, preferably 4-6 ethyleneoxy groups. - 0 In an advantageous mode of execution, ethylene oxide can be added in a first step and thereafter alkylene oxide having 3-4 carbon atoms. These compounds can be illustrat¬ ed by the formula
15 C5Hι:ιCH(C3H7)CH20(C2H40) (B)rH (II)
wherein B is an alkyleneoxy group having 3-4 carbon atoms, p is 1-10 and r is 1-6. Preferably, p is 2-8 and r is 1-4. These compounds have lower foaming than the corresponding
2„ compounds without any alkyleneoxy groups having 3-4 carbon atoms.
The alkoxylates for use according to the invention described above can be prepared by adding in a conven¬ tional manner in the presence of a conventional alkali catalyst, such as potassium hydroxide or sodium hydroxide, the above-mentioned amounts of alkylene oxide to 2-propyl heptanol, which is a so-called Guebert alcohol. According to a preferred mode of execution, the addition of ethylene oxide is performed using a conventional catalyst which gives a narrower distribution of added ethylene oxide than any alkali catalyst, such as NaOH or KOH. Thus prepared alkoxylates according to the invention have very low foam¬ ing. Examples of conventional catalysts giving a narrow distribution of added alkylene oxide are CaζOH)-, Ba(OH)...,
~r Sr(OH)^ and hydrotalcite. The reaction is preferably con¬ ducted in the absence of free water to reduce the amount of by-products and usually at a temperature of 70-180°C. The alkoxylate, especially ethoxylate and alkoxylate of formula II, is suitably included in compositions for cleaning hard surfaces, e.g. for degreasing or dishwash¬ ing. Especially good results have been obtained when degreasing lacquered or unlacquered metal surfaces. In addition to the alkoxylate, the compositions may also con¬ tain other detergents, such as anionic surface-active com¬ pounds. Examples hereof are alkyl sulphate, alkyl ether sulphate, alkyl benzene sulphonate, α-olefin sulphonate and alkyl glyceryl sulphonate. Also, the compositions may contain solutising additives, complexing agents and/or pH-ad usting agents, enzymes, other surface-active compo¬ nents, bactericides and perfumes. The compositions are usually aqueous and in the form of emulsions, microemul- sions or solutions.
The invention will be further illustrated by the fol¬ lowing Examples.
Example 1 Alkoxylates according to the invention are prepared by alkoxylating 2-propyl ethanol with the amounts of alky¬ lene oxide appearing from the Table below in the presence of potassium hydroxide or Ca(0H)_ as catalyst. The result¬ ing products were analysed and structurally determined by gas chromatography and mass spectrometry. The turbidity points were measured in water or monobutylether diethylene glycol. The following results were obtained.
Table 1
Figure imgf000006_0001
EO = ethylene oxide; PO = propylene oxide,
BDG = monobutylether diethylene glycol 1) PO added first 2) Dobanol 91 from Shell
3) Dobanol 1 from Shell
Example 2
The foaming properties of the alkoxylates reported in the following Table were measured according to Ross-Miles ASTM D 1173-53. The following results were obtained. Table 2
Figure imgf000007_0001
From these results it appears that the compounds ac¬ cording to the invention have lower foaming than the most closely related reference products. Thus, compound 2 has lower foaming than compounds A, B, C, D and E, while com¬ pounds 4, 5 and 6 have lower foaming than all the refe¬ rence compounds.
Example 3
On a vertically disposed, lacquered iron plate, smeared with mineral oils, soot, salts and clay was applied 20 ml of a detergent composition made up of the following components.
Figure imgf000007_0002
The effect achieved was evaluated both with respect to the area of the cleaned surface (i.e. wettability) and with respect to the cleanness of the cleaned surface. Cleanness was evaluated according to an ascending scale of 1-10, where 1 indicates that no improvement of the clean¬ ness could be observed and 10 indicates a completely clean surface. The following results were obtained.
Table 3
Figure imgf000008_0001
From these results it appears that the formulation containing the compound according to the invention yield¬ ed both improved cleanness and a larger cleaned area.
Example 4
The microtoxicity, which is a measure of the aquatic toxicity, was determined for the compounds below as the water concentration of the compounds at which the ability of luminescent bacteria to emit light for 5 min is reduced by 50%. The following results were obtained.
Table 4
Figure imgf000008_0002
From these results it appears that the compounds according to the invention have essentially lower micro¬ toxicity than the reference compounds.

Claims

C A I M S
1. The use of an alkoxylate having the general formula
C5H11CH(C3H7)CH20(A)nH (I) wherein A is an alkyleneoxy group having 2-4 carbon atoms and n is 2-16, preferably 3-12, in a detergent composition for hard surfaces.
2. Use as claimed in claim 1, c h a r a c t e r i s ¬ e in that 50-100% of all the alkyleneoxy groups are ethyleneoxy groups.
3. Use as claimed in claim 1, c h a r a c t e r i s ¬ e d in that A is ethyleneoxy groups and n is 3-7.
4. Use as claimed in claim 1 or 2, c h a r a c t e r ¬ i s e d by having the formula C5H1;LCH(C3H7)CH20(C2H40)p(B)rH (II) wherein B is an alkyleneoxy group having 3-4 carbon atoms, p is 1-10 and r is 1-6, p preferably being 2-8 and r pre¬ ferably being 1-4.
5. Use as claimed in any one of claims 1-4, c h a r ¬ a c t e r i s e d in that the detergent composition is a composition for degreasing unlacquered or lacquered metal surfaces.
6. An alkoxylate, c h a r a c t e r i s e d by having the formula
C5Hi;LCH(C3H7)CH20(C2H40)p(B)rH (II) wherein B is an alkyleneoxy group having 3-4 carbon atoms, p is 1-10 and r is 1-6, p preferably being 2-8 and r pre¬ ferably being 1-4.
PCT/SE1993/000966 1992-11-19 1993-11-12 Use of alkoxylate of 2-propyl heptanol WO1994011331A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
JP51200594A JP4104650B2 (en) 1992-11-19 1993-11-12 How to use alkoxylates
EP94901106A EP0669906B1 (en) 1992-11-19 1993-11-12 Alkoxylate of 2-propyl heptanol and use thereof
US08/436,268 US5608118A (en) 1992-11-19 1993-11-12 Alkoxylate of 2-propyl heptanol and detergent containing same
CA002148705A CA2148705C (en) 1992-11-19 1993-11-12 Alkoxylate of 2-propyl heptanol and use thereof
DE69310925T DE69310925T2 (en) 1992-11-19 1993-11-12 2-PROPYLHEPTANOL ALKOXYLATE AND ITS USE
NO951962A NO303220B1 (en) 1992-11-19 1995-05-18 Alkoxylate of 2-propylheptanol and its use
FI952430A FI107913B (en) 1992-11-19 1995-05-18 2-Propylheptanol alkoxylate and its use

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE9203478-4 1992-11-19
SE9203478A SE501132C2 (en) 1992-11-19 1992-11-19 Use of alkoxylate of 2-propylheptanol in cleaning compositions

Publications (1)

Publication Number Publication Date
WO1994011331A1 true WO1994011331A1 (en) 1994-05-26

Family

ID=20387871

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/SE1993/000966 WO1994011331A1 (en) 1992-11-19 1993-11-12 Use of alkoxylate of 2-propyl heptanol
PCT/SE1993/000967 WO1994011330A1 (en) 1992-11-19 1993-11-12 Alkoxylate of 2-propyl heptanol and use thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/SE1993/000967 WO1994011330A1 (en) 1992-11-19 1993-11-12 Alkoxylate of 2-propyl heptanol and use thereof

Country Status (11)

Country Link
US (2) US5608118A (en)
EP (2) EP0669906B1 (en)
JP (2) JPH08502993A (en)
AT (2) ATE153328T1 (en)
CA (2) CA2148705C (en)
DE (2) DE69310926T2 (en)
ES (2) ES2105602T3 (en)
FI (2) FI110775B (en)
NO (2) NO304550B1 (en)
SE (1) SE501132C2 (en)
WO (2) WO1994011331A1 (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0845449A1 (en) * 1996-11-27 1998-06-03 Akzo Nobel N.V. Ethoxylate mixture and a cleaning composition for hard surfaces containing the ethoxylate mixture
US6548714B1 (en) 1998-09-05 2003-04-15 Basf Aktiengesellschaft Method for producing polyetherols by ring-opening polymerisation of alkylene oxides
WO2003091192A1 (en) * 2002-04-26 2003-11-06 Basf Aktiengesellschaft C10-alkanolalkoxylate mixtures and the use thereof
WO2003091190A1 (en) 2002-04-26 2003-11-06 Basf Aktiengesellschaft Alkoxylate mixtures and detergents containing the same
WO2003091191A1 (en) * 2002-04-26 2003-11-06 Basf Aktiengesellschaft C10-alkanolalkoxylates and the use thereof
WO2004033405A1 (en) * 2002-09-18 2004-04-22 Basf Aktiengesellschaft Alkoxylates exhibiting low residual alcohol content
WO2004033404A1 (en) * 2002-09-18 2004-04-22 Basf Aktiengesellschaft Method for producing alkoxylated products at optimized reaction pressures
WO2006005721A1 (en) * 2004-07-15 2006-01-19 Akzo Nobel N.V. Phosphated alcanol, its use as a hydrotrope and cleaning composition containing the compound
US7348460B2 (en) 2002-09-18 2008-03-25 Basf Aktiengesellschaft Method for producing alkanol alkoxylates at optimal reaction temperatures
AU2004281952B2 (en) * 2003-10-14 2010-11-25 Basf Aktiengesellschaft C10 alkanolalkoxylate mixtures and use thereof as novel low-foaming wetting agents
US8653016B2 (en) 2009-11-25 2014-02-18 Basf Se Biodegradable cleaning composition
US9381450B2 (en) 2008-12-18 2016-07-05 Akzo Nobel N.V. Defoamer composition comprising alkoxylated 2-propylheptanol
EP3399013A1 (en) 2017-05-05 2018-11-07 The Procter & Gamble Company Laundry detergent compositions with improved grease removal
EP3399012A1 (en) 2017-05-05 2018-11-07 The Procter & Gamble Company Liquid detergent compositions with improved rheology

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10065058A1 (en) * 2000-12-27 2002-07-11 Sasol Germany Gmbh Composition, useful for the production of film and articles, comprises a polyvinylacetate homo- or mixed polymer and an alkoxylated alcohol
JP3894288B2 (en) * 2001-10-18 2007-03-14 株式会社Ａｄｅｋａ Emulsifier for emulsion polymerization or dispersant for suspension polymerization
EP1501355B1 (en) * 2002-04-24 2010-05-19 Basf Se Use of defined alcohol alkoxylates as adjuvants in the agrotechnical field
SE526170C2 (en) 2003-05-07 2005-07-19 Akzo Nobel Nv Aqueous composition containing an alkylene oxide adduct, a hexyl glucoside and an active nonionic alkylene oxide adduct as a wetting agent
DE102004007152A1 (en) 2004-02-12 2005-08-25 Basf Ag Novel alkyl ether sulfates useful as anionic surfactants in detergents, cleansing or cosmetic compositions or chemical-technical applications have alkylene oxide units between the alcohol component and sulfate group
EP1591466A1 (en) * 2004-04-26 2005-11-02 Basf Aktiengesellschaft Preparation of a polyether composition
DE102004039941A1 (en) * 2004-08-17 2006-02-23 Basf Ag Wetting agent for impregnating resins
JP5210177B2 (en) 2006-02-22 2013-06-12 ビーエーエスエフ ソシエタス・ヨーロピア Surfactant mixture containing short and long chain components
BRPI0714838A2 (en) 2006-07-24 2013-04-02 Basf Se use of a composition, and process for obtaining oil and / or natural gas
US8119717B2 (en) * 2006-11-21 2012-02-21 Basf Corporation Coating composition having a low volatile organic compound content
WO2008068307A2 (en) * 2006-12-07 2008-06-12 Basf Se Compositions and kits comprising a fungicidal triazole and an alkoxylated alcohol, and their uses
US8431639B2 (en) 2007-11-08 2013-04-30 Basf Corporation Wetting additive and composition including the same
WO2010072029A1 (en) 2008-12-25 2010-07-01 Dow Global Technologies Inc. Surfactant compositions with wide ph stability
MX2010004526A (en) * 2009-04-30 2010-11-01 Basf Se Dispersing agent.
US10087399B2 (en) * 2012-07-13 2018-10-02 Basf Se Use of alkoxylated non-ionic surfactants as additive in aqueous membrane cleaning compositions
JP6272882B2 (en) * 2012-10-11 2018-01-31 ビーエーエスエフ エスイー Surfactant for aqueous coating
PL3636691T3 (en) 2015-10-07 2021-09-27 Elementis Specialties, Inc. Wetting and anti-foaming agent
BR112018073598B1 (en) * 2016-05-17 2022-09-27 Unilever Ip Holdings B.V LIQUID COMPOSITION FOR WASHING CLOTHES AND USE OF A LIQUID COMPOSITION DETERGENT FOR WASHING CLOTHES
AU2017267050B2 (en) 2016-05-17 2020-03-05 Unilever Global Ip Limited Liquid laundry detergent compositions
US10421926B2 (en) 2017-01-20 2019-09-24 Ecolab Usa Inc. Cleaning and rinse aid compositions and emulsions or microemulsions employing optimized extended chain nonionic surfactants
AU2018214226B2 (en) * 2017-02-03 2023-07-13 Grains Research And Development Corporation (Grdc) Methods to enhance soil water infiltration and to reduce soil water repellency using a surfactant composition
US11873465B2 (en) 2019-08-14 2024-01-16 Ecolab Usa Inc. Methods of cleaning and soil release of highly oil absorbing substrates employing optimized extended chain nonionic surfactants
TW202408360A (en) 2022-05-11 2024-03-01 以色列商安道麥馬克西姆有限公司 Phthalimide fungicide composition

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3567784A (en) * 1969-06-13 1971-03-02 Shell Oil Co Alcohol alkoxylates
EP0046582A1 (en) * 1980-08-22 1982-03-03 Conoco Inc. (formerly called : DU PONT HOLDINGS , INC.) Inorganic catalyst for alkoxylation of alcohols
GB2145726A (en) * 1983-08-26 1985-04-03 Diversey Corp Surface active agents
CH674358A5 (en) * 1986-08-28 1990-05-31 Colgate Palmolive Co

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2508036A (en) * 1950-05-16 Compounds having high wetting
NL134504C (en) * 1965-06-28
US3862243A (en) * 1972-02-17 1975-01-21 Int Flavors & Fragrances Inc Mixed oxyalkylates employed as antifoamers
DE2448532A1 (en) * 1973-10-15 1975-04-24 Procter & Gamble OIL REMOVAL COMPOSITIONS
US4410447A (en) * 1980-11-12 1983-10-18 Union Carbide Corporation Low-foaming nonionic surfactants
US4340382A (en) * 1980-12-16 1982-07-20 Union Carbide Corporation Method for treating and processing textile materials
DE3818183A1 (en) * 1988-05-28 1989-12-07 Basf Ag METHOD FOR DYING LEATHER WITH PIGMENTS

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3567784A (en) * 1969-06-13 1971-03-02 Shell Oil Co Alcohol alkoxylates
EP0046582A1 (en) * 1980-08-22 1982-03-03 Conoco Inc. (formerly called : DU PONT HOLDINGS , INC.) Inorganic catalyst for alkoxylation of alcohols
GB2145726A (en) * 1983-08-26 1985-04-03 Diversey Corp Surface active agents
CH674358A5 (en) * 1986-08-28 1990-05-31 Colgate Palmolive Co

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0845449A1 (en) * 1996-11-27 1998-06-03 Akzo Nobel N.V. Ethoxylate mixture and a cleaning composition for hard surfaces containing the ethoxylate mixture
US6548714B1 (en) 1998-09-05 2003-04-15 Basf Aktiengesellschaft Method for producing polyetherols by ring-opening polymerisation of alkylene oxides
US7335235B2 (en) 2002-04-26 2008-02-26 Basf Akiengesellschaft Alkoxylate mixtures and detergents containing the same
WO2003091192A1 (en) * 2002-04-26 2003-11-06 Basf Aktiengesellschaft C10-alkanolalkoxylate mixtures and the use thereof
WO2003091190A1 (en) 2002-04-26 2003-11-06 Basf Aktiengesellschaft Alkoxylate mixtures and detergents containing the same
WO2003091191A1 (en) * 2002-04-26 2003-11-06 Basf Aktiengesellschaft C10-alkanolalkoxylates and the use thereof
US7419552B2 (en) 2002-04-26 2008-09-02 Basf Aktiengesellschaft C10-alkanol alkoxylates and the use thereof
US7371716B2 (en) 2002-04-26 2008-05-13 Basf Aktiengesellschaft C10-alkanolalkoxylate mixtures and the use thereof
US7348460B2 (en) 2002-09-18 2008-03-25 Basf Aktiengesellschaft Method for producing alkanol alkoxylates at optimal reaction temperatures
WO2004033405A1 (en) * 2002-09-18 2004-04-22 Basf Aktiengesellschaft Alkoxylates exhibiting low residual alcohol content
US7332465B2 (en) 2002-09-18 2008-02-19 Basf Aktiengesellschaft Alkoxylates exhibiting low residual alcohol content
CN1296337C (en) * 2002-09-18 2007-01-24 巴斯福股份公司 Alkoxylates exhibiting low residual alcohol content
US7196030B2 (en) 2002-09-18 2007-03-27 Basf Aktiengesellschaft Method for producing alkoxylated products at optimized reaction pressures
WO2004033404A1 (en) * 2002-09-18 2004-04-22 Basf Aktiengesellschaft Method for producing alkoxylated products at optimized reaction pressures
AU2004281952B2 (en) * 2003-10-14 2010-11-25 Basf Aktiengesellschaft C10 alkanolalkoxylate mixtures and use thereof as novel low-foaming wetting agents
AU2004281952B8 (en) * 2003-10-14 2011-01-20 Basf Aktiengesellschaft C10 alkanolalkoxylate mixtures and use thereof as novel low-foaming wetting agents
US8519196B2 (en) 2003-10-14 2013-08-27 Basf Aktiengesellschaft C10 alkanolalkoxylate mixtures and use thereof as novel low-foaming wetting agents
US7456144B2 (en) 2004-07-15 2008-11-25 Akzo Nobel N.V. Phosphated alcanol, its use as a hydrotrope and cleaning composition containing the compound
US7671006B2 (en) 2004-07-15 2010-03-02 Akzo Nobel N.V. Phosphated alcanol, its use as a hydrotrope and cleaning composition containing the compound
WO2006005721A1 (en) * 2004-07-15 2006-01-19 Akzo Nobel N.V. Phosphated alcanol, its use as a hydrotrope and cleaning composition containing the compound
US9381450B2 (en) 2008-12-18 2016-07-05 Akzo Nobel N.V. Defoamer composition comprising alkoxylated 2-propylheptanol
US8653016B2 (en) 2009-11-25 2014-02-18 Basf Se Biodegradable cleaning composition
EP3399013A1 (en) 2017-05-05 2018-11-07 The Procter & Gamble Company Laundry detergent compositions with improved grease removal
EP3399012A1 (en) 2017-05-05 2018-11-07 The Procter & Gamble Company Liquid detergent compositions with improved rheology
WO2018204560A1 (en) 2017-05-05 2018-11-08 The Procter & Gamble Company Liquid detergent compositions with improved rheology
WO2018204559A1 (en) 2017-05-05 2018-11-08 The Procter & Gamble Company Laundry detergent compositions with improved grease removal

Also Published As

Publication number Publication date
FI952431A0 (en) 1995-05-18
DE69310925T2 (en) 1997-08-28
NO951961L (en) 1995-05-18
US5608118A (en) 1997-03-04
ATE153327T1 (en) 1997-06-15
CA2148705C (en) 2004-06-15
CA2148706A1 (en) 1994-05-26
NO304550B1 (en) 1999-01-11
NO951962D0 (en) 1995-05-18
CA2148706C (en) 2005-04-12
ES2104333T3 (en) 1997-10-01
NO303220B1 (en) 1998-06-15
DE69310925D1 (en) 1997-06-26
NO951962L (en) 1995-05-18
FI110775B (en) 2003-03-31
EP0669906B1 (en) 1997-05-21
SE9203478D0 (en) 1992-11-19
SE9203478L (en) 1994-05-20
FI952430A (en) 1995-05-18
EP0669906A1 (en) 1995-09-06
EP0669907B1 (en) 1997-05-21
JPH08502993A (en) 1996-04-02
ES2105602T3 (en) 1997-10-16
JPH08502992A (en) 1996-04-02
SE501132C2 (en) 1994-11-21
JP4104650B2 (en) 2008-06-18
FI952430A0 (en) 1995-05-18
ATE153328T1 (en) 1997-06-15
NO951961D0 (en) 1995-05-18
US5661121A (en) 1997-08-26
DE69310926T2 (en) 1997-08-28
EP0669907A1 (en) 1995-09-06
CA2148705A1 (en) 1994-05-26
FI107913B (en) 2001-10-31
DE69310926D1 (en) 1997-06-26
WO1994011330A1 (en) 1994-05-26
FI952431A (en) 1995-05-18

Similar Documents

Publication Publication Date Title
WO1994011331A1 (en) Use of alkoxylate of 2-propyl heptanol
EP0210220B1 (en) Method and compositions for hard surface cleaning
CA1158518A (en) Liquid detergent composition
EP0399752B1 (en) Light-duty liquid or gel dishwashing detergent composition containing an alkyl ethoxy carboxylate surfactant
US6048831A (en) Surfactant composition
EP0690868B1 (en) Alkyl glucoside and use thereof
JP4568832B2 (en) Alkoxylate mixture and its use as a hard surface cleaner
EP0092877A2 (en) Detergent compositions
RU2007105588A (en) PHOSPHATIC ALKANOL, ITS USE AS A HYDROTROP AND CLEANING COMPOSITION CONTAINING THIS COMPOUND
US5644041A (en) Alkyl glycoside its use for cleaning purposes, and cleaning composition
US3994818A (en) Substantially non-aqueous low foaming liquid non-ionic detergent composition
GB2088863A (en) Novel Alkyl-polyoxyalkylene Carboxylate Surfactants
KR20000010805A (en) Alkyl polyglycoside ether carboxylates
US4954283A (en) Polyethylene glycol ether low temperature foam suppressing agents in low-foam cleaning agents
JP2801075B2 (en) Detergent composition
JPH05214392A (en) Detergent composition
JP2005060450A (en) Liquid detergent composition
CA1261881A (en) Low foaming surfactant
JPH1112594A (en) Liquid cleaner composition
JPH11116522A (en) New ether compound, antifoaming agent and low-frothing detergent composition
JPH09503539A (en) Low foaming cleaning composition
MXPA98000441A (en) s off. THE USE OF ALKOXILATED ALCOHOLS TO CONTROL THE FOAM OF POLYGLICOSIDES IN LIMPI COMPOSITIONS
EP0620269A1 (en) Cleaning composition
KR20050016913A (en) An alkoxylate mixture and its use as a cleaning agent for hard surfaces
JPH11106789A (en) Foam inhibitor and slightly foaming detergent composition

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA FI JP NO US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
ENP Entry into the national phase

Ref document number: 2148706

Country of ref document: CA

Ref country code: CA

Ref document number: 2148706

Kind code of ref document: A

Format of ref document f/p: F

WWE Wipo information: entry into national phase

Ref document number: 2148705

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 08436268

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 952430

Country of ref document: FI

WWE Wipo information: entry into national phase

Ref document number: 1994901106

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1994901106

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1994901106

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 952430

Country of ref document: FI