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WO2005063847A1 - Composes de polyol alcoxyles modifies - Google Patents

Composes de polyol alcoxyles modifies Download PDF

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Publication number
WO2005063847A1
WO2005063847A1 PCT/US2004/043074 US2004043074W WO2005063847A1 WO 2005063847 A1 WO2005063847 A1 WO 2005063847A1 US 2004043074 W US2004043074 W US 2004043074W WO 2005063847 A1 WO2005063847 A1 WO 2005063847A1
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WO
WIPO (PCT)
Prior art keywords
hydroxy moieties
capping unit
compound
anionic
alkoxy moiety
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2004/043074
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English (en)
Inventor
Jeffrey John Scheibel
Julie Ann Menkhaus
Xinbei Song
Eva Schneiderman
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Procter and Gamble Co
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Procter and Gamble Co
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Filing date
Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to EP04815188A priority Critical patent/EP1694741A1/fr
Priority to CA002549571A priority patent/CA2549571A1/fr
Priority to BRPI0417536-0A priority patent/BRPI0417536A/pt
Priority to MXPA06007020A priority patent/MXPA06007020A/es
Priority to JP2006544144A priority patent/JP2007520459A/ja
Priority to CN2004800378221A priority patent/CN1894305B/zh
Publication of WO2005063847A1 publication Critical patent/WO2005063847A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C07H15/08—Polyoxyalkylene derivatives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene 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
    • C11D1/88—Ampholytes; Electroneutral compounds

Definitions

  • This invention relates to modified alkoxylated polyol compounds, methods of making modified alkoxylated polyol compounds, and cleaning compositions comprising the same.
  • Polyol compounds such as sugars like sucrose or maltitose are known as a sustainable and readily available raw material.
  • Ethoxyates of maltitol is known, e.g., CAS 503446-80-8. This material has been widely disclosed as a surfactant for cosmetic and other personal care applications such as that discussed in JP 2003-096182.
  • Other known ethoxylated polyols include: ethoxylated manitol (CAS 53047-01-2), ethoxylated inostol (CAS 503446-79-5), ethoxylated sorbitol (CAS 53694-15-8).
  • JP 10-081744 discusses the production of polyetherpolyols by adding alkylene oxides to saccharide in the presence of amine catalysts.
  • Catalyst implies, the amine catalysts do not become incorporated into the polyetherpolyol structure.
  • a series of amine terminated ethoxylates known in the trade as JEFF AMINES® sold by Huntsman. These are mainly derived from polyethylene glycol and mixtures of polyethylene glycol and polypropylene glycol where the glycols are aminated directly with ammonia and a catalyst. These are called JEFF AMINE D® and JEFF AMINE ED® series. The most complex mixture of the JEFF AMINES® series is the T series.
  • the JEFFAMINES® are based on either trimethylolpropane or glycerine and thus have three ammonia terminated ethoxy/propoxy branches radiating from the glycerin or trimethylolpropane core.
  • Amination of polyols with ammonia and other amines is further exemplified in US 5,371,119, but uses modification of the polyol specifically via epichlorohydrin to form a polyol bis-halohydrin followed by reaction with ammonia or an amine to form repeating networks of amino polyols. This results in formation of a complex polymerized mixture containing multiple polyols linked randomly via the reactive halo hydrin.
  • This complex mixture is not believed to be of value to formulators of cleaning compositions for the purpose of providing cleaning benefits and is targeted towards forming emulsifiers.
  • Simple amination of polyols are described in WO 01/98388 Al discussing simple aminated polyols, further reacted with aldehydes, in particular formaldehyde, to make complex polymeric networks. Included in these complex structures is the ability to have sulf ⁇ de, carboxylate, alkyl esters, alkyl sulphonates, and alkyl phosphates as a functional unit of the complex structure.
  • the resulting complex polymeric networks is not believed to be of value to formulators of cleaning compositions for the purpose of providing cleaning benefits.
  • a multifunctional material that provides cleaning and gives increased surfactant availability by preventing formation of larger ordered aggregates of anionic surfactant with free hardness during use is desired.
  • Specific performance requirements include providing cleaning of hydrophobic stains (grease, oil) to hydrophilic stains (clay) associated with outdoor soils.
  • compositions such as contact lens solution, uses in adhesives, vulcanization of rubbers, use in polyurethane processes, use as dye additives, use as a dispersant in agricultural applications, use as dispersants for inks, asphalt dispersants, surfactant dissolution aides, in use surfactant solubilizers in presence of calcium and magnesium among other performance requirements.
  • Formulability of some of the current commercial polymers, which provide cleaning of outdoor soils, into granular and liquid laundry detergents, hard surface cleaners, dish cleaning compositions, personal care compositions as well as oil drilling compositions continues to challenge detergent formulators.
  • the present invention relates to compounds, processes, cleaning compositions, and methods of using said compounds and compositions characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties further comprise an anionic capping unit.
  • the present invention further relates compounds, processes, cleaning compositions, and methods of using said compounds and compositions characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties is replaced by and thus further comprises an anionic capping unit and at least one of the hydroxy moieties is substituted by an amine capping unit.
  • the present invention further relates compounds, processes, cleaning compositions, and methods of using said compounds and compositions characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties is replaced by and thus further comprises an anionic capping unit and at least one of the hydroxy moieties is substituted by a quaternary amine capping unit.
  • the present invention further relates compounds, processes, cleaning compositions, and methods of using said compounds and compositions characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties is replaced by and thus further comprises an anionic capping unit, at least one of the hydroxy moieties is substituted by an amine capping unit and at least one of the hydroxy moieties is substituted by a quaternary amine capping unit.
  • an alkoxylated polyol compound modified by comprising an anionic capping unit and amine capping unit is a tuned structure giving desired characteristics.
  • Another example is when an alkoxylated polyol compound is modified by comprising an anionic capping unit and a quaternary amine capping unit, is a tuned structure giving desired characteristics.
  • Finally another example may contain both elements of the two examples, thus containing an anionic capping unit and an amine and quaternary amine capping unit.
  • the polyol compounds useful in the present invention comprises at least three hydroxy moieties, preferably more than three hydroxy moieties. Most preferably six or more hydroxy moieties.
  • At least one of the hydroxy moieties further comprising a alkoxy moiety is selected from the group consisting of ethoxy (EO), propoxy (PO), butoxy (BO) and mixtures thereof preferably ethoxy and propoxy moieties, more preferably ethoxy moieties.
  • the average degree of alkoxylation is from about 1 to about 100, preferably from about 4 to about 60, more preferably from about 10 to about 40.
  • Alkoxylation is preferably block alkoxylation.
  • the polyol compounds useful in the present invention further have at least one of the alkoxy moieties comprising at least one anionic capping unit. Further modifications or tuning of the compound may occur, but one anionic capping unit must be present in the compound of the present invention.
  • One embodiment comprises more than one hydroxy moiety further comprising an alkoxy moiety having an anionic capping unit.
  • Suitable anionic capping unit include sulfate, sulfosuccinate, succinate, maleate, phosphate, phthalate, sulfocarboxylate, sulfodicarboxylate, propanesultone, 1,2-disulfopropanol, sulfopropylamine, sulphonate, monocarboxylate, methylene carboxylate, ethylene carboxylate, carbonates, mellitic, pyromellitic, sulfophenol, sulfocatechol, disulfocatechol, tartrate, citrate, acrylate, methacrylate, poly acrylate, poly acrylate-maleate copolymer, and mixtures thereof.
  • the anionic capping units are sulfate, sulfosuccinate, succinate, maleate, sulfonate, methylene carboxylate and ethylene carboxylate.
  • Suitable polyol compounds for starting materials for use in the present invention include maltitol, sucrose, xylitol, glycerol, pentaerythitol, glucose, maltose, matotriose, maltodextrin, maltopentose, maltohexose, isomaltulose, sorbitol, poly vinyl alcohol, partially hydrolyzed polyvinylacetate, xylan reduced maltotriose, reduced maltodextrins, polyethylene glycol, polypropylene glycol, polyglycerol, diglycerol ether and mixtures thereof.
  • Good examples include the polyol compound being selected as sorbitol, maltitol, sucrose, xylan, polyethylene glycol, polypropylene glycol and mixtures thereof. Another group for the polyol compound is sorbitol, maltitol, sucrose, xylan, and mixtures thereof.
  • Tuning of the polyol compounds can be derived from one or more modifications, dependant upon the desired formulability and performance requirements. Tuning requires anionic modifications and can include incorporating a cationic or zwitterionic charge modifications to the polyol compounds.
  • at least one hydroxy moiety comprises an alkoxy moiety, wherein the alkoxy moiety further comprises at least one anionic capping unit.
  • At least one hydroxy moiety comprises an alkoxy moiety, wherein the alkoxy moiety further comprises more than one anionic capping unit, wherein at least one anionic capping unit, but less than all anionic capping units, is then selectively substituted by a amine capping unit.
  • the amine capping unit is selected from a primary amine containing capping unit, a secondary amine containing capping unit, a tertiary amine containing capping unit, and mixtures thereof.
  • Suitable primary amines for the primary amine containing capping unit include monoamines, diamine, triamine, polyamines, and mixtures thereof.
  • Suitable secondary amines for the secondary amine containing capping unit include monoamines, diamine, triamine, polyamines, and mixtures thereof.
  • Suitable tertiary amines for the tertiary amine containing capping unit include monoamines, diamine, triamine, polyamines, and mixtures thereof.
  • Suitable monoamines, diamines, triamines or polyamines for use in the present invention include ammonia, methyl amine, dimethylamine, ethylene diamine, dimethylaminopropylamine, bis dimethylaminopropylamine (bis DMAPA), hexemethylene diamine, benzylamine, isoquinoline, ethylamine, diethylamine, dodecylamine, tallow triethylenediamine, mono substituted monoamine, monosubstituted diamine, monosubstituted polyamine, disubstituted monoamine, disubstiuted diamine, disubstituted polyamine, trisubstituted triamine, tri-substituted polyamine, multisubstituted polyamine comprising more than three substitutions provided at least one nitrogen contains a hydrogen, and mixtures thereof.
  • At least one of nitrogens in the amine capping unit is quaternized.
  • quaternized means that the amine capping unit is given a positive charge through quaternization or protonization of the amine capping unit.
  • bis-DMAPA contains three nitrogens, only one of the nitrogens need be quaternized. However, it is preferred to have all nitrogens quaternized on any given amine capping unit.
  • the tuning or modification may be combined depending upon the desired formulability and performance requirements.
  • Non-limiting examples of modified polyol compounds of the present invention include:
  • formula (II) wherein x of formula (I) is from about 1 to about 100; and such as from about 10 to about 40.
  • the present invention also relates to a process for making the compound of the present invention.
  • the process for making the compound of the present invention comprises the optional step of alkoxylating a polyol compound comprising at least three hydroxy moieties such that the average degree of alkoxylation of at least one hydroxy moiety is between about 1 and about 100; and such as from about 4 to about 60; further such as from about 10 to about 40; to form an alkoxylated polyol comprising at least one alkoxy moiety.
  • an alkoxylated polyol such as CAS 52625-13-5, a propoxylated sorbitol or sorbitol polyoxy ethylene ether available from Lipo Chemicals Inc., may be used as the starting material of the present invention.
  • an alkoxylation step may be used to achieve the desired degree of alkoxylation from about 1 to about 100, and such as from about 4 to about 60; further such as from about 10 to about 40.
  • the process comprises the step of reacting at least one alkoxy moiety of the compound with an anionic capping unit to form an anionic alkoxylated polyol, although more anionic capping units may be selected.
  • the process comprises another step of substituting at least one anionic capping unit of the anionic alkoxylated polyol with an amine capping unit to form an anionic aminated alkoxylated polyol.
  • anionic capping units may be substituted such as sulfate, phosphate and carbonate.
  • the process may further comprise the step of quaternizing at least one of the nitrogens in the amine capping of the anionic aminated alkoxylated polyol to form a zwitterionic alkoxylated polyol. Quaternization can be performed on any of the anionic aminated alkoxylated polyols.
  • the process comprises the step of alkoxylating some or most of the hydroxy moieties of the polyol such that the degree of alkoxylation is from about 1 to about 100; and such as from about 4 to about 60, further such as from about 10 to about 40; to form an alkoxylated polyol.
  • the process further comprises the step of reacting the alkoxy moiety of the alkoxylated polyol with at least one anionic capping unit containing as least one of the following anionic groups; sulfate, phosphate and carbonate; to form an anionic alkoxylated polyol.
  • the process may partially or completely react the alkoxy moiety of the alkoxylated polyol with an anionic capping unit.
  • anionic capping units other than sulfate, phosphate or carbonate may also be present in the anionic alkoxylated polyol.
  • all alkoxy moieties comprise an anionic capping unit.
  • the process comprises the step of substituting the anionic capping unit with an amine capping unit selected from sulfate, phosphate and carbonate and mixtures thereof, to form an aminated anionic alkoxylated polyol (scheme I below).
  • the substitution of the anionic capping units present with an amine capping unit may be partial or complete.
  • the subsitution of the anionic capping unit with the amine capping unit is partial forming an anionic aminated alkoxylated polyol.
  • the process also comprises the process of providing an aminated alkoxylated polyol by direct amination of the alkoxylated polyol using catalytic amination (scheme II below)
  • the process may further comprise the step of quaternizing at least one of the nitrogens of the amine capping unit of the anionic aminated alkoxylated polyol forming a zwitterionic alkoxylated polyol.
  • the quaternization of the amine capping unit of the anionic aminated alkoxylated polyol may be partial or complete. In one embodiment, the quaternization is partial. In another embodiment, the quaternization is complete.
  • the quaternization of the nitrogens of the amine capping unit may be partial or complete, preferably complete.
  • a nonlimiting synthesis scheme is exemplified in Synthesis Scheme I and Synthesis Scheme II below:
  • the process may comprise optionally Step 1, Step 2, and optionally, Step 3 and 4.
  • the step to providing the anionic aminated alkoxylated polyol via a neucleophilic substitution of sulfate moieties by an amine capping unit should be noted. This is a nonlimiting example as phosphate or carbonate groups may also be used for substitution by an amine capping unit.
  • Scheme II is distinguished from Scheme I in two areas; (1) direct substitution of the terminal hydroxy moieties is accomplished by catalytic oxidation/reduction using metal catalysts and hydrogen; (2) sulfation is carried out after amination and quaternization by transulfation as disclosed in US 6,452,035.
  • a zwitterionic alkoxylated polyol of the same composition may be prepared by either Scheme I or Scheme II above.
  • One of skill in the art will recognized that other amine capping units may be used, including but not limited to ammonia or dimethylaminopropylamine. A specific description of the process of the present invention is described in more detail below.
  • Ethoxylation of Polyol may be completed by any known technique, such as that described in EP 174436 Al Propoxylation and butoxylation may also be completed by known techniques.
  • the methanol from the methoxide solution is removed from the autoclave under vacuum.
  • a device is used to monitor the power consumed by the agitator.
  • the agitator power is monitored along with the temperature and pressure. Agitator power and temperature values gradually increase as methanol is removed from the autoclave and the viscosity of the mixture increases and stabilizes in about 1.5 hours indicating that most of the methanol has been removed.
  • the mixture is further heated and agitated under vacuum for an additional 30 minutes. Vacuum is removed and the autoclave is cooled to or kept at 110° C. while it is being charged with nitrogen to 1725 kPa (250 psia) and then vented to ambient pressure. The autoclave is charged to 1380 kPa (200 psia) with nitrogen.
  • Ethylene oxide is added to the autoclave incrementally while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate while maintaining the temperature between 110 and 120° C. and limiting any temperature increases due to reaction exotherm.
  • the temperature is increased to 120° C. and the mixture stirred for an additional 2 hours.
  • the reaction mixture is then collected into a 22 L three neck round bottomed flask purged with nitrogen.
  • the strong alkali catalyst is neutralized by slow addition of 2.8g methanesulfonic acid (0.00288 moles) with heating (110° C.) and mechanical stirring.
  • reaction mixture is then purged of residual ethylene oxide and deodorized by sparging an inert gas (argon or nitrogen) into the mixture through a gas dispersion frit while agitating and heating the mixture to 120° C. for 1 hour.
  • an inert gas argon or nitrogen
  • the final reaction product approximately 500g, is cooled slightly, and poured into a glass container purged with nitrogen for storage.
  • polyol may be purchased with a degree of alkoxylation that is at or below that desired, such as CAS 52625-13-5, a propoxylated sorbitol or sorbitol polyoxy ethylene ether available from Lipo Chemicals Inc. Wherein the desired degree of alkoxylation is achieved by the processes known and/or described above.
  • Example 2 Amination of Sorbitol EO Hexasulfate Of Example 1
  • the present invention further relates to a cleaning composition comprising the modified alkoxylated polyol compound of the present invention.
  • the cleaning compositions can be in any conventional form, namely, in the form of a liquid, powder, granules, agglomerate, paste, tablet, pouches, bar, gel, types delivered in dual-compartment containers, spray or foam detergents, premoistened wipes (i.e., the cleaning composition in combination with a nonwoven material such as that discussed in US 6,121,165, Mackey, et al.), dry wipes (i.e., the cleaning composition in combination with a nonwoven materials, such as that discussed in US 5,980,931, Fowler, et al.) activated with water by a consumer, and other homogeneous or multiphase consumer cleaning product forms.
  • premoistened wipes i.e., the cleaning composition in combination with a nonwoven material such as that discussed in US 6,121,165, Mackey, et al.
  • dry wipes i.e., the cleaning composition in combination with a nonwoven materials, such as that discussed in US 5,980,931,
  • the compounds of the present invention may be also suitable for use or incorporation into industrial cleaners (i.e. floor cleaners). Often these cleaning compositions will additionally comprise surfactants and other cleaning adjunct ingredients, discussed in more detail below.
  • the cleaning composition of the present invention is a liquid or solid laundry detergent composition.
  • the cleaning composition of the present invention is a hard surface cleaning composition, preferably wherein the hard surface cleaning composition impregnates a nonwoven substrate. As used herein "impregnate" means that the hard surface cleaning composition is placed in contact with a nonwoven substrate such that at least a portion of the nonwoven substrate is penetrated by the hard surface cleaning composition, preferably the hard surface cleaning composition saturates the nonwoven substrate.
  • the cleaning composition is a liquid dish cleaning composition, such as liquid hand dishwashing compositions, solid automatic dishwashing cleaning compositions, liquid automatic dishwashing cleaning compositions, and tab/unit does forms of automatic dishwashing cleaning compositions.
  • the cleaning composition may also be utilized in car care compositions, for cleaning various surfaces such as hard wood, tile, ceramic, plastic, leather, metal, glass.
  • This cleaning composition could be also designed to be used in a personal care composition such as shampoo composition, body wash, liquid or solid soap and other cleaning composition in which surfactant comes into contact with free hardness and in all compositions that require hardness tolerant surfactant system, such as oil drilling compositions.
  • the cleaning composition of the present invention may comprise from about 0.005% to about 30%, and such as from about 0.01% to about 10%, further such as from about 0.05%o to about 5% by weight of the cleaning composition of a modified polyol compound as described herein.
  • the cleaning composition of the present invention may comprise a surfactant or surfactant system comprising surfactants selected from nonionic, anionic, cationic, ampholytic, zwitterionic, semi-polar nonionic surfactants; and other adjuncts such as alkyl alcohols, or mixtures thereof.
  • the cleaning composition of the present invention further comprises from about from about 0.01% to about 90%, and such as from about 0.01% to about 80%, further such as from about 0.05% to about 50%, more further such as from about 0.05% to about 40%) by weight of the cleaning composition of a surfactant system having one or more surfactants.
  • anionic surfactants include: C 8 -C ⁇ 8 alkyl benzene sulfonates (LAS); C ⁇ 0 -C 20 primary, branched-chain and random alkyl sulfates (AS); C ⁇ 0 -C ⁇ 8 secondary (2,3) alkyl sulfates; Cjo-C )S alkyl alkoxy sulfates (AE X S) wherein x is from 1-30; C ⁇ 0 - C[ 8 alkyl alkoxy carboxylates comprising 1-5 ethoxy units; mid-chain branched alkyl sulfates as discussed in US 6,020,303 and US 6,060,443; mid-chain branched alkyl alkoxy sulfates as discussed in US 6,008,181 and US 6,020,303; modified alkylbenzene sulfonate (MLAS) as discussed in WO 99/05243, WO 99/05242
  • MLAS modified alkylbenzene
  • Non-limiting examples of nonionic surfactants include: C ⁇ 2 -C ⁇ 8 alkyl ethoxylates, such as, NEODOL ® nonionic surfactants from Shell; C ⁇ -C ⁇ alkyl phenol alkoxylates wherein the alkoxylate units are a mixture of ethyleneoxy and propyleneoxy units; C ]2 -C ⁇ 8 alcohol and C 6 -C ⁇ 2 alkyl phenol condensates with ethylene oxide/propylene oxide block alkyl polyamine ethoxylates such as PLURONIC ® from BASF; C ⁇ 4 -C 22 mid-chain branched alcohols, BA, as discussed in US 6,150,322; C ⁇ 4 -C 22 mid-chain branched alkyl alkoxylates, BAE Xj wherein x 1-30, as discussed in US 6,153,577, US 6,020,303 and US 6,093,856; Alkylpolysaccharides as discussed in U.S.
  • anionic surfactants include: the quaternary ammonium surfactants, which can have up to 26 carbon atoms include: alkoxylate quaternary ammonium (AQA) surfactants as discussed in US 6,136,769; dimethyl hydroxyethyl quaternary ammonium as discussed in 6,004,922; polyamine cationic surfactants as discussed in WO 98/35002, WO 98/35003, WO 98/35004, WO 98/35005, and WO 98/35006; cationic ester surfactants as discussed in US Patents Nos 4,228,042, 4,239,660 4,260,529 and US 6,022,844; and amino surfactants as discussed in US 6,221,825 and WO 00/47708, specifically amido propyldimethyl amine (APA).
  • AQA alkoxylate quaternary ammonium
  • Non-limiting examples of zwitterionic surfactants include: derivatives of secondary and tertiary amines, derivatives of heterocyclic secondary and tertiary amines, or derivatives of quaternary ammonium, quaternary phosphonium or tertiary sulfonium compounds. See U.S. Patent No.
  • betaine including alkyl dimethyl betaine and cocodimethyl amidopropyl betaine, C 8 to s ( 2 to C i8 ) amine oxides and sulfo and hydroxy betaines, such as N-alkyl-N,N-dimethylammino-l -propane sulfonate where the alkyl group can be C 8 to C ⁇ 8 , Cio to C [ .
  • ampholytic surfactants include: aliphatic derivatives of secondary or tertiary amines, or aliphatic derivatives of heterocyclic secondary and tertiary amines in which the aliphatic radical can be straight- or branched-chain.
  • One of the aliphatic substituents contains at least about 8 carbon atoms, typically from about 8 to about 18 carbon atoms, and at least one contains an anionic water-solubilizing group, e.g. carboxy, sulfonate, sulfate. See U.S. Patent No.
  • Non-limiting examples of semi-polar nonionic surfactants include: water-soluble amine oxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms; water-soluble phosphine oxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms; and water-soluble sulfoxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and a moiety selected from the group consisting of alkyl and hydroxyalkyl moieties of from about 1 to about 3 carbon atoms
  • a cleaning adjunct is any material required to transform a cleaning composition containing only the minimum essential ingredients into a cleaning composition useful for laundry, hard surface, personal care, consumer, commercial and/or industrial cleaning purposes.
  • cleaning adjuncts are easily recognizable to those of skill in the art as being absolutely characteristic of cleaning products, especially of cleaning products intended for direct use by a consumer in a domestic environment.
  • the precise nature of these additional components, and levels of incorporation thereof, will depend on the physical form of the cleaning composition and the nature of the cleaning operation for which it is to be used.
  • the cleaning adjunct ingredients if used with bleach should have good stability therewith.
  • Certain embodiments of cleaning compositions herein should be boron-free and/or phosphate-free as required by legislation. Levels of cleaning adjuncts are from about 0.00001% to about 99.9%, and such as from about 0.0001% to about 50% by weight of the cleaning compositions.
  • cleaning compositions herein such as laundry detergents, laundry detergent additives, hard surface cleaners, synthetic and soap-based laundry bars, fabric softeners and fabric treatment liquids, solids and treatment articles of all kinds will require several adjuncts, though certain simply formulated products, such as bleach additives, may require only, for example, an oxygen bleaching agent and a surfactant as described herein.
  • a comprehensive list of suitable laundry or cleaning adjunct materials can be found in WO 99/05242.
  • Common cleaning adjuncts include builders, enzymes, polymers not discussed above, bleaches, bleach activators, catalytic materials and the like excluding any materials already defined hereinabove.
  • Other cleaning adjuncts herein can include suds boosters, suds suppressors (antifoams) and the like, diverse active ingredients or specialized materials such as dispersant polymers (e.g., from BASF Corp.
  • the present invention includes a method for cleaning a surface or fabric. Such method includes the steps of contacting a modified alkoxylated polyol compound of the present invention or an embodiment of the cleaning composition comprising the modified alkoxylated polyol compound of the present invention, in neat form or diluted in a wash liquor, with at least a portion of a surface or fabric then optionally rinsing such surface or fabric. Preferably the surface or fabric is subjected to a washing step prior to the aforementioned optional rinsing step. For purposes of the present invention, washing includes but is not limited to, scrubbing, and mechanical agitation.
  • the cleaning compositions of the present invention are ideally suited for use in home care (hard surface cleaning compositions), personal care and/or laundry applications. Accordingly, the present invention includes a method for cleaning a surface and/or laundering a fabric. The method comprises the steps of contacting a surface and/or fabric to be cleaned/laundered with the modified alkoxylated polyol compound or a cleaning composition comprising the modified alkoxylated polyol compound.
  • the surface may comprise most any hard surface being found in a typical home such as hard wood, tile, ceramic, plastic, leather, metal, glass, or may consist of a cleaning surfaces in a personal care product such as hair and skin.
  • the surface may also include dishes, glasses, and other cooking surfaces.
  • the fabric may comprise most any fabric capable of being laundered in normal consumer use conditions.
  • the cleaning composition solution pH is chosen to be the most complimentary to a surface to be cleaned spanning broad range of pH, from about 5 to about 11.
  • For personal care such as skin and hair cleaning pH of such composition preferably has a pH from about 5 to about 8 for laundry cleaning compositions pH of from about 8 to about 10.
  • the compositions are preferably employed at concentrations of from about 200 ppm to about 10,000 ppm in solution.
  • the water temperatures preferably range from about 5 °C to about 100 °C.
  • the compositions are preferably employed at concentrations from about 200 ppm to about 10000 ppm in solution (or wash liquor).
  • the water temperatures preferably range from about 5°C to about 60°C.
  • the water to fabric ratio is preferably from about 1:1 to about 20:1.
  • the present invention included a method for cleaning a surface or fabric. Such method includes the step of contacting a nonwoven substrate impregnated with an embodiment of the cleaning composition of the present invention, and contacting the nonwoven substrate with at least a portion of a surface and/or fabric.
  • the method may further comprise a washing step. For purposes of the present invention, washing includes but is not limited to, scrubbing, and mechanical agitation.
  • the method may further comprise a rinsing step.
  • nonwoven substrate can comprise any conventionally fashioned nonwoven sheet or web having suitable basis weight, caliper (thickness), absorbency and strength characteristics.
  • the cleaning compositions of the present invention are ideally suited for use in hard surface applications.
  • the present invention includes a method for cleaning hard surfaces.
  • the method comprises the steps of contacting a hard surface to be cleaned with a hard surface solution or nonwoven substrate impregnated with an embodiment of the cleaning composition of the present invention.
  • the method of use comprises the steps of contacting the cleaning composition with at least a portion of the nonwoven substrate, then contacting a hard surface by the hand of a user or by the use of an implement to which the nonwoven substrate attaches.
  • the cleaning compositions of the present invention are ideally suited for use in liquid dish cleaning compositions.
  • the method for using a liquid dish composition of the present invention comprises the steps of contacting soiled dishes with an effective amount, typically from about 0.5 ml. to about 20 ml. (per 25 dishes being treated) of the liquid dish cleaning composition of the present invention diluted in water. Suitable examples may be seen below in Table 5.
  • an effective amount typically from about 0.5 ml. to about 20 ml. (per 25 dishes being treated) of the liquid dish cleaning composition of the present invention diluted in water.
  • Suitable examples may be seen below in Table 5.
  • from about 0.01 ml. to about 150 ml. of a liquid dish cleaning composition of the invention is combined with from about 2000 ml. to about 20000 ml of water in a sink having a volumetric capacity in the range of from about 1000 ml. to about 20000 ml..
  • the soiled dishes are immersed in the sink containing the diluted compositions then obtained, where contacting the soiled surface of the dish with a cloth, sponge, or similar article cleans them.
  • the cloth, sponge, or similar article may be immersed in the detergent composition and water mixture prior to being contacted with the dish surface, and is typically contacted with the dish surface for a period of time ranged from about 1 to about 10 seconds.
  • the contacting of cloth, sponge, or similar article to the dish surface is preferably accompanied by a concurrent scrubbing of the dish surface.
  • Another method of use will comprise immersing the soiled dishes into a water bath without any liquid dish cleaning composition.
  • a device for absorbing liquid dish cleaning composition such as a sponge, is placed directly into a separate quantity of undiluted liquid dish cleaning composition for a period of time typically ranging from about 1 to about 5 seconds.
  • the absorbing device, and consequently the undiluted liquid dish cleaning composition is then contacted individually to the surface of each of the soiled dishes to remove said soiling.
  • the absorbing device is typically contacted with each dish surface for a period of time range from about 1 to about 10 seconds.
  • the contacting of the absorbing device to the dish surface is preferably accompanied by concurrent scrubbing.
  • the cleaning compositions of the present invention are also suited for use in personal cleaning care applications. Accordingly, the present invention includes a method for cleaning skin or hair.
  • the method comprises the steps of contacting a skin / hair to be cleaned with a cleaning solution or nonwoven substrate impregnated with an embodiment of the cleaning compositions discussed herein.
  • the method of use of the nonwoven substrate when contacting skin and hair may be by the hand of a user or by the use of an implement to which the nonwoven substrate attaches.
  • Other Compositions Other compositions that comprise the compound of the present invention may be used in personal care compositions, such as contact lens solution, used as adhesives, in the vulcanization of rubbers, used in polyurethane manufacturing processes, used in dye compositions, used as an ink composition, used as a dispersant in agricultural applications, such as a dispersant in an antifungal composition, among other compositions.
  • Protease - Proteolytic enzyme having 3.3% by weight of active enzyme, sold by NOVO Industries A/S under the tradename SAVINASE®; Proteolytic enzyme, having 4% by weight of active enzyme, as described in WO 95/10591, sold by Genencor Int. Inc.
  • Alcalase- Proteolytic enzyme having 5.3% by weight of active enzyme, sold by NOVO Industries A S
  • Cellulase - Cellulytic enzyme having 0.23% by weight of active enzyme, sold by NOVO Industries A S under the tradename CAREZYME®.
  • Amylase - Amylolytic enzyme having 1.6% by weight of active enzyme, sold by NOVO Industries A/S under the tradename TERMAMYL 120T®; Amylolytic enzyme, as disclosed in PCT/ US9703635.
  • Lipase - Lipolytic enzyme having 2.0% by weight of active enzyme, sold by NOVO Industries A/S under the tradename LIPOLASE®; Lipolytic enzyme, having 2.0% by weight of active enzyme, sold by NOVO
  • Endolase - Endoglucanase enzyme having 1.5% by weight of active enzyme, sold by NOVO Industries
  • Zeolite A Hydrated Sodium AluminosiUcate of formula Nai 2(A102Si ⁇ 2)i2- 27 ⁇ 0 having a primary particle size in the range from 0.1 to 10 micrometers

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Abstract

L'invention concerne un composé de polyol modifié présentant une alcoxylation et renfermant au moins une unité de coiffage anionique, les utilisations de ce composé de polyol modifié présentant une alcoxylation et renfermant au moins une unité de coiffage anionique, ainsi que des compositions nettoyantes comprenant ledit composé.
PCT/US2004/043074 2003-12-19 2004-12-17 Composes de polyol alcoxyles modifies Ceased WO2005063847A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP04815188A EP1694741A1 (fr) 2003-12-19 2004-12-17 Composes de polyol alcoxyles modifies
CA002549571A CA2549571A1 (fr) 2003-12-19 2004-12-17 Composes de polyol alcoxyles modifies
BRPI0417536-0A BRPI0417536A (pt) 2003-12-19 2004-12-17 compostos de poliol alcoxilado modificados
MXPA06007020A MXPA06007020A (es) 2003-12-19 2004-12-17 Compuestos de poliol alcoxilado modificado.
JP2006544144A JP2007520459A (ja) 2003-12-19 2004-12-17 修飾されたアルコキシル化ポリオール化合物
CN2004800378221A CN1894305B (zh) 2003-12-19 2004-12-17 改性的烷氧基化多元醇化合物

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US53138503P 2003-12-19 2003-12-19
US60/531,385 2003-12-19

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006066059A1 (fr) * 2004-12-17 2006-06-22 The Procter & Gamble Company Polyols modifies de maniere hydrophobe pour un meilleur nettoyage des salissures hydrophobes
WO2006066060A1 (fr) * 2004-12-17 2006-06-22 The Procter & Gamble Company Polyols modifies de maniere hydrophobe pour un meilleur nettoyage des salissures hydrophobes
WO2007144819A1 (fr) 2006-06-12 2007-12-21 The Procter & Gamble Company Produit pour lingette imbibée de lotion comprenant un agent antiadhésif et un agent d'améliorations de performances
US8093352B2 (en) 2008-08-05 2012-01-10 Alcon Research, Ltd. Polyalkylene oxide polyquaternary ammonium biocides
CN115734978A (zh) * 2020-06-30 2023-03-03 阿科玛法国公司 改进的烷氧基化工艺

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9119779B2 (en) 2006-06-12 2015-09-01 The Procter & Gamble Company Lotioned wipe product comprising an anti-stick agent and a performance enhancing agent
CN105732442B (zh) * 2016-01-27 2017-11-03 江苏苏博特新材料股份有限公司 低聚型表面活性剂、其制备方法及应用
EP4229027A4 (fr) * 2020-10-19 2024-10-23 Oxiteno S.A. Indústria e Comércio Composition, formulation agrochimique, procédés pour augmenter la disponibilité de l'eau et des nutriments et pour améliorer la lutte contre les organismes nuisibles dans les plantes et les graines, et utilisations de la composition et de la formulation agrochimique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4927961A (en) * 1986-10-01 1990-05-22 Th. Goldschmidt Ag Polyoxyalkylene ether having hydroxyl and sulfonate groups and their use in the preparation of dispersable polyurethanes
US4990269A (en) * 1985-01-03 1991-02-05 Berol Kemi Ab Surface active compound, a microemulsion containing said compound and the use thereof
US20020142929A1 (en) * 2001-01-05 2002-10-03 Smith George A. Advanced sulfosuccinamate surfactants

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS591784A (ja) * 1982-06-24 1984-01-07 東邦化学工業株式会社 ポリエステル系合成繊維又はポリエステル／セルロ−ス系繊維混交品用染色助剤
JPH06306041A (ja) * 1993-04-23 1994-11-01 Kao Corp モノグリセリドジ硫酸塩及び該ジ硫酸塩を含有するモノグリセリド硫酸塩の製法
ES2127364T3 (es) * 1993-08-10 1999-04-16 Ciba Geigy Ag Humectantes de mercerizado.
US5650234A (en) * 1994-09-09 1997-07-22 Surface Engineering Technologies, Division Of Innerdyne, Inc. Electrophilic polyethylene oxides for the modification of polysaccharides, polypeptides (proteins) and surfaces
DE4441363A1 (de) * 1994-11-21 1996-05-23 Huels Chemische Werke Ag Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf Basis von Di-, Oligo- oder Polyolethern
US5686603A (en) * 1995-05-04 1997-11-11 Lever Brothers Company, Division Of Conopco, Inc. Sulfated polyhydroxy compounds as anionic surfactants and a process for their manufacture
JPH09249636A (ja) * 1996-03-19 1997-09-22 Kao Corp Ｎ−アルキルアミドアルカノール硫酸エステル塩の製造方法
JPH10279553A (ja) * 1997-04-03 1998-10-20 Lion Corp （ポリ）グリセリルエーテル硫酸塩の製造方法
JP2001097942A (ja) * 1999-09-28 2001-04-10 Kao Corp モノグリセライドサルフェートの製造法
JP4208462B2 (ja) * 2000-12-28 2009-01-14 株式会社Ａｄｅｋａ 界面活性剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4990269A (en) * 1985-01-03 1991-02-05 Berol Kemi Ab Surface active compound, a microemulsion containing said compound and the use thereof
US4927961A (en) * 1986-10-01 1990-05-22 Th. Goldschmidt Ag Polyoxyalkylene ether having hydroxyl and sulfonate groups and their use in the preparation of dispersable polyurethanes
US20020142929A1 (en) * 2001-01-05 2002-10-03 Smith George A. Advanced sulfosuccinamate surfactants

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006066059A1 (fr) * 2004-12-17 2006-06-22 The Procter & Gamble Company Polyols modifies de maniere hydrophobe pour un meilleur nettoyage des salissures hydrophobes
WO2006066060A1 (fr) * 2004-12-17 2006-06-22 The Procter & Gamble Company Polyols modifies de maniere hydrophobe pour un meilleur nettoyage des salissures hydrophobes
US7326675B2 (en) 2004-12-17 2008-02-05 Procter & Gamble Company Hydrophobically modified polyols for improved hydrophobic soil cleaning
US7332467B2 (en) 2004-12-17 2008-02-19 Procter & Gamble Company Hydrophilically modified polyols for improved hydrophobic soil cleaning
WO2007144819A1 (fr) 2006-06-12 2007-12-21 The Procter & Gamble Company Produit pour lingette imbibée de lotion comprenant un agent antiadhésif et un agent d'améliorations de performances
US8093352B2 (en) 2008-08-05 2012-01-10 Alcon Research, Ltd. Polyalkylene oxide polyquaternary ammonium biocides
CN115734978A (zh) * 2020-06-30 2023-03-03 阿科玛法国公司 改进的烷氧基化工艺

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EP1694741A1 (fr) 2006-08-30
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MXPA06007020A (es) 2006-08-31
CN1894305B (zh) 2010-10-13
CA2549571A1 (fr) 2005-07-14

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