CN1894305A - Modified alkoxylated polyol compounds - Google Patents
Modified alkoxylated polyol compounds Download PDFInfo
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- CN1894305A CN1894305A CNA2004800378221A CN200480037822A CN1894305A CN 1894305 A CN1894305 A CN 1894305A CN A2004800378221 A CNA2004800378221 A CN A2004800378221A CN 200480037822 A CN200480037822 A CN 200480037822A CN 1894305 A CN1894305 A CN 1894305A
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- 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
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Abstract
A modified polyol compound having alkoxylation and having at least one anionic capping unit, uses of the modified polyol compound having alkoxylation and having at least one anionic capping unit and cleaning compositions comprising the same.
Description
Invention field
The present invention relates to the alkoxylated polyol compounds of modification, the method for alkoxylated polyol compounds of preparation modification and the cleaning compositions that comprises this compound.
Background of invention
Be known as the raw material of in liberal supply and easy acquisition such as the polyol compound of carbohydrate (as sucrose or maltose).The ethoxylate of maltose alcohol is known, for example, and CAS503446-80-8.This material is open widely as the tensio-active agent quilt that is used for makeup and other personal care application, as discussing among the JP 2003-096182.Other known ethoxylation polyvalent alcohol comprises: ethoxylation mannitol (CAS 53047-01-2), ethoxylation inositol (CAS 503446-79-5), ethoxylated sorbitol (CAS 53694-15-8).JP 10-081744 has discussed in the presence of amine catalyst and has produced polyether glycol by adding alkylene oxide to carbohydrate.Yet, such as " catalyzer " hint, amine catalyst is not introduced on the structure of polyether glycol.
Known commodity are called JEFFAMINES
And the end capped ethoxylate of being sold by Huntsman of a series of amine also is known.Mainly derived from the mixture of polyoxyethylene glycol and polyoxyethylene glycol and polypropylene glycol, wherein said dibasic alcohol is directly used ammonia and a kind of catalyzer amination for these.These are called as JEFFAMINE D
With JEFFAMINE ED
Series.Most of JEFFAMINES
The complex mixture of series is a T series.Described JEFFAMINES
Therefore based on TriMethylolPropane(TMP) or glycerine, and have three the end capped oxyethyl group of ammonia/propoxy-side chains that go out from glycerine or TriMethylolPropane(TMP) nuclear radiation.
Come the amination polyvalent alcohol further to be illustrated in US 5,371,119 with ammonia and other amine, but be to use the modification of polyvalent alcohol.Specifically, by epoxy chloropropane to form polyvalent alcohol dihalo alcohol, next by with ammonia or amine reaction to form the recurrent network of amino polyol.This causes forming the complicated polymeric mixture that comprises multiple polyvalent alcohol by the random connection of active halohydrin.This complex mixture is considered to the formulator of the cleaning compositions that aims to provide the cleaning beneficial effect is not worth, and it is intended to form emulsifying agent.
The simple amination of polyvalent alcohol is described in WO 01/98388 A1, and it has discussed simple aminating polyvalent alcohol, further reacts to prepare complicated polymer network with aldehyde (formaldehyde specifically).Be included in these complex constructions is to have sulfide, carboxylate, alkyl ester, alkylsulfonate and the alkylphosphonic ability as the complex construction functional unit.Yet the complicated polymer network of gained is considered to the formulator of the cleaning compositions that aims to provide the cleaning beneficial effect is not worth.In addition, use these materials also not report in controlled and concrete mode.The selectivity modification of sugar deutero-polyvalent alcohol to be to provide the polyvalent alcohol of modification, wherein is adjustable to cater to star topology that the washing composition formulator requires and is highly needs.
Also have the demand for following material, it is than the feedstock production that is easier to by in liberal supply and easy acquisition, and this material can be adjusted widely to satisfy concrete performance requriements.
Be subjected to also to cause additional problem under the situation of stress: the alkylbenzene sulfonate or the bigger ordered aggregation of alkylsurfuric acid salt formation that make anion surfactant such as straight chain.The gathering of anion surfactant has reduced the amount of the anion surfactant that can be used to clean.Also have the demand for following material, it is than the feedstock production that is easier to by in liberal supply and easy acquisition, and this material can controlled and concrete mode be adjusted to satisfy concrete preparation and performance requriements.Expect to have a kind of multifunctional material, its provide in use cleaning effect and can by prevent anion surfactant with not fixedly the formation of the bigger orderly aggregate of hardness face the tensio-active agent availability of increase is provided.
Concrete performance requriements comprises the hydrophobic spot (grease, oil) that provides relevant with the outdoor dirt cleaning to hydrophilic spot (clay).Other performance requriements comprises and is used for personal care composition, as contact lens solutions, be used for the sulfuration of tackiness agent, rubber, be used for urethane technology, as dye additive, as the dispersion agent of agricultural application, dispersion agent, pitch dispersion agent, surfactant dissolves auxiliary agent as ink are applied to the surface active agent solubilization agent in the presence of calcium and magnesium in other performance requriements.
Become the some current commercial polymer preparation that outdoor soil cleaning is provided granular and liquid laundry detergent, hard surface cleaners, dish cleaning compositions, personal care composition and oil drilling composition, for the washing composition formulator, remain a challenge.
Summary of the invention
The present invention relates to the method for compound, technology, cleaning compositions and the described compound of use, and composition is characterised in that it comprises polyol compound, described polyol compound comprises at least three hydroxylic moieties, in the described hydroxylic moiety at least one also comprises the alkoxyl group part, and described alkoxyl group partly is selected from oxyethyl group, propoxy-, butoxy and their mixture; In the wherein said in addition hydroxylic moiety at least one also comprises a negatively charged ion end-blocking unit.
The invention still further relates to the method for compound, technology, cleaning compositions and the described compound of use, and composition is characterised in that and comprises polyol compound, described polyol compound comprises at least three hydroxylic moieties, in the described hydroxylic moiety at least one also comprises the alkoxyl group part, and described alkoxyl group partly is selected from oxyethyl group, propoxy-, butoxy and their mixture; Wherein at least one in the hydroxylic moiety is by a negatively charged ion end-blocking replacement unit and therefore also comprise a negatively charged ion end-blocking unit in addition, and in the described hydroxylic moiety at least one replaced by an amine end-blocking unit.
The invention still further relates to the method for compound, technology, cleaning compositions and the described compound of use, and composition is characterised in that and comprises polyol compound, described polyol compound comprises at least three hydroxylic moieties, in the described hydroxylic moiety at least one also comprises the alkoxyl group part, and described alkoxyl group partly is selected from oxyethyl group, propoxy-, butoxy and their mixture; Wherein at least one in the hydroxylic moiety is by a negatively charged ion end-blocking replacement unit and therefore also comprise a negatively charged ion end-blocking unit in addition, and in the described hydroxylic moiety at least one replaced by a quaternary ammonium end-blocking unit.
The invention still further relates to the method for compound, technology, cleaning compositions and the described compound of use, and composition is characterised in that and comprises polyol compound, described polyol compound comprises at least three hydroxylic moieties, in the described hydroxylic moiety at least one also comprises the alkoxyl group part, and described alkoxyl group partly is selected from oxyethyl group, propoxy-, butoxy and their mixture; In addition wherein at least one in the hydroxylic moiety by a negatively charged ion end-blocking replacement unit and therefore also comprise a negatively charged ion end-blocking unit, in the described hydroxylic moiety at least one replaced by an amine end-blocking unit, and in the described hydroxylic moiety at least one replaced by a quaternary ammonium end-blocking unit.
Detailed Description Of The Invention
Also have the demand for following material, it is than the feedstock production that is easier to by in liberal supply and easy acquisition, and this material can be adjusted widely to satisfy concrete preparation and performance requriements.
(for example, sugar) material and polyethylene/polypropylene glycol material are in liberal supply and the raw material of easy acquisition, and it can make their own adjustment widely to satisfy concrete preparation and performance requriements based on polyol compound." adjustment " used herein is meant to have and controls the polyol compound chemical structure dexterously to realize distinguishing chemical functionality's ability.For example, be a kind of structure of adjustment by comprising the oxyalkylated polyol compound that a negatively charged ion end-blocking unit is modified, it provides desired characteristic for concrete preparation and performance requriements.Another one embodiment is to be a kind of adjustment structure that desired characteristic is provided by comprising the oxyalkylated polyol compound that a negatively charged ion end-blocking unit and amine end-blocking unit be modified.Another one embodiment is that this compound is a kind of adjustment structure that desired characteristic is provided when oxyalkylated polyol compound is modified by comprising a negatively charged ion end-blocking unit and a quaternary ammonium end-blocking unit.Therefore last embodiment can comprise the key element of above-mentioned two examples, comprises a negatively charged ion end-blocking unit and amine and quaternary ammonium end-blocking unit.
Can be used for polyol compound of the present invention and comprise at least three hydroxylic moieties, preferably more than three hydroxylic moieties.Most preferably six or more hydroxylic moiety.In the described hydroxylic moiety at least one also comprises an alkoxyl group part, and described alkoxyl group partly is selected from oxyethyl group (EO), propoxy-(PO), butoxy (BO) and their mixture, preferred oxyethyl group and propoxy-part, more preferably oxyethyl group part.Average degree of alkoxylation is about 1 to about 100, and preferred about 4 to about 60, more preferably from about 10 to about 40.The preferred end capped oxyalkylation of oxyalkylation.
Can be used for polyol compound of the present invention also has at least one and comprises the unitary alkoxyl group part of at least one negatively charged ion end-blocking.Compound is further modified or adjusted and can occur, must only have a negatively charged ion end-blocking unit to be present in the compound of the present invention.An embodiment comprises more than one hydroxylic moiety, and this hydroxylic moiety also comprises and has the unitary alkoxyl group part of negatively charged ion end-blocking.Formula (I) for example:
Formula (I)
The x of its Chinese style (I) is about 1 to about 100, or for example about 10 to about 40.
Suitable negatively charged ion end-blocking unit comprises vitriol, sulfosuccinic ester, succinate, maleate, phosphoric acid salt, phthalate, the sulfocarboxylic acid esters, the sulfo group dicarboxylic ester, propane sultone, 1,2-dithio propyl alcohol, the sulfo group propylamine, sulfonate, monocarboxylate, methylene carboxylate, ethylene carboxylate, carbonate, mellate, pyromellitic acid salt, sulfo group phenol, the sulfo group catechol, the disulfo catechol, tartrate, Citrate trianion, acrylate, methacrylate, polyacrylate, polyacrylic ester salt-maleate copolymer and their mixture.Preferably, described negatively charged ion end-blocking unit is vitriol, sulfosuccinate, succinate, maleate, sulfonate, methylene carboxylate and ethylene carboxylate.
Be used for polyvinyl acetate, xylan, reductive trisaccharide maltose, reductive Star Dri 5, polyoxyethylene glycol, polypropylene glycol, Polyglycerine, Glycerol dimer ether and their mixture that suitable polyol compound that the present invention is used as raw material comprises maltose alcohol, sucrose, Xylitol, glycerine, tetramethylolmethane, glucose, maltose, trisaccharide maltose, Star Dri 5, Fructus Hordei Germinatus pentose, Fructus Hordei Germinatus hexose, Palatinose, sorbyl alcohol, polyvinyl alcohol, partial hydrolysis.Good embodiment comprises polyol compound, is selected from sorbyl alcohol, maltose alcohol, sucrose, xylan, polyoxyethylene glycol, polypropylene glycol and their mixture.Another group polyol compound is sorbyl alcohol, maltose alcohol, sucrose, xylan and their mixture.
The adjustment of polyol compound can be modified derived from one or more, and this depends on required preparation and performance requriements.Adjustment needs anion modified and can comprise to polyol compound introducing positively charged ion or the modification of zwitterionic electric charge.
In one embodiment of the invention, at least one hydroxylic moiety comprises an alkoxyl group part, and wherein said alkoxyl group part also comprises at least one negatively charged ion end-blocking unit.
In another embodiment of the invention, at least one hydroxylic moiety comprises an alkoxyl group part, wherein said alkoxyl group part also comprises an above negatively charged ion end-blocking unit, wherein at least one negatively charged ion end-blocking unit but be not that all negatively charged ion end-blocking unit are optionally replaced by amine end-blocking unit.Described amine end-blocking unit is selected from the end-blocking unit that comprises primary amine, the end-blocking unit that comprises secondary amine, the end-blocking unit that comprises tertiary amine and their mixture.
Comprise monoamine, diamines, triamine, polyamines and their mixture for comprising the unitary suitable primary amine of primary amine end-blocking.Comprise monoamine, diamines, triamine, polyamines and their mixture for comprising the unitary suitable secondary amine of secondary amine end-blocking.Comprise monoamine, diamines, triamine, polyamines and their mixture for comprising tertiary amine capped unitary suitable tertiary amine.
Be used for suitable monoamine of the present invention, diamines, triamine or polyamines comprise ammonia, methylamine, dimethylamine, 1, the 2-quadrol, dimethylamino propylamine, two dimethylamino propylamines (two DMAPA), hexanediamine, benzylamine, isoquinoline 99.9, ethamine, diethylamine, lauryl amine, the butter triethylenediamine, monobasic monoamine, monobasic diamines, monobasic polyamines, dibasic monoamine, dibasic diamines, dibasic polyamines, trisubstituted triamine, trisubstituted polyamines, comprise polysubstituted polyamines (precondition is that at least one nitrogen comprises a hydrogen) more than three replacements, and their mixture.
In another embodiment of the invention, at least one nitrogen in amine end-blocking unit is quaternised." quaternised " used herein is meant by the amine end-blocking unitary quaternized or protonated, offers amine end-blocking unit positive charge.For example, two DMAPA comprise three nitrogen, needs are only arranged by quaternized in these nitrogen.Yet, preferably on any given amine end-blocking unit, give all nitrogen quaternized.
Described adjustment or modification can combine, and this depends on required preparation and performance requriements.The non-limiting example of the polyol compound of modification of the present invention comprises:
Formula (II)
X in its Chinese style (I) is about 1 to about 100 and for example about 10 to about 40.
Formula (III)
Formula (IV)
The preparation method
The present invention also relates to a kind of method that can be used for preparing compound of the present invention.The method that is used to prepare compound of the present invention comprises following optional step: alkoxylate comprises the polyol compound of at least three hydroxylic moieties, so that the average degree of alkoxylation of at least one hydroxylic moiety is between about 1 and about 100; For example about 4 to about 60; For example about 10 to about 40; The alkoxylated polyol that comprises at least one alkoxyl group part with formation.Alternatively, alkoxylated polyol, for example, and CAS 52625-13-5, propoxylation sorbyl alcohol or sorbitol polyoxyethylene ether available from Lipo ChemicalsInc. can be used as raw material of the present invention.If average degree of alkoxylation is not required level, can use the alkoxylate step to realize that required degree of alkoxylation is about 1 to about 100 and for example about 4 to about 60; For example about 10 to about 40.Then, said method comprising the steps of: with at least one alkoxyl group part and the unit process of a negatively charged ion end-blocking of compound, to form the oxyalkylated polyvalent alcohol of negatively charged ion, although can select more negatively charged ion end-blocking unit.
In one embodiment, described method comprises another step: replace at least one negatively charged ion end-blocking unit of described negatively charged ion alkoxylated polyol with amine end-blocking unit, to form the aminating alkoxylated polyol of negatively charged ion.In the method, only some negatively charged ion end-blocking unit such as vitriol, phosphoric acid salt and carbonate can be substituted.Described method also can may further comprise the steps: the nitrogen in the amine end-blocking of the aminating alkoxylated polyol of at least one negatively charged ion is quaternized, and to form the zwitter-ion alkoxylated polyol.Quaternized can on any one of the aminating alkoxylated polyol of described negatively charged ion, carrying out.In one embodiment, described method may further comprise the steps: the some or most of hydroxyl groups parts of alkoxylate, so that degree of alkoxylation is about 1 to about 100; For example about 4 to about 60 and for example about 10 to about 40; To form alkoxylated polyol.Described method is further comprising the steps of: with alkoxyl group part and at least one negatively charged ion end-blocking unit process of alkoxylated polyol, this negatively charged ion end-blocking unit comprises at least one following anionic group: vitriol, phosphoric acid salt and carbonate; To form the negatively charged ion alkoxylated polyol.Described method can partially or even wholly make the alkoxyl group part and the unit process of negatively charged ion end-blocking of alkoxylated polyol.Should also be understood that the negatively charged ion end-blocking unit except vitriol, phosphoric acid salt or carbonate also can be present in described negatively charged ion alkoxylated polyol.Preferred all alkoxyl groups partly comprise a negatively charged ion end-blocking unit.
Randomly, said method comprising the steps of: replace described negatively charged ion end-blocking unit with the amine end-blocking unit that is selected from vitriol, phosphoric acid salt and carbonate and their mixture, to form aminating negatively charged ion alkoxylated polyol (following scheme I).Can replace the negatively charged ion end-blocking unit that exists with an amine end-blocking unit partially or completely.Preferably, replace negatively charged ion end-blocking unit with described amine end-blocking unit, part forms the aminating alkoxylated polyol of negatively charged ion.
Randomly, described method also comprises following method: by using the direct amination alkoxylated polyol of Study on Catalytic Amination of Alcohols, provide aminating alkoxylated polyol (following scheme II).
Randomly, described method also can may further comprise the steps: the nitrogen in the amine end-blocking unit of the aminating alkoxylated polyol of at least one negatively charged ion is quaternized, and to form the zwitter-ion alkoxylated polyol.Amine end-blocking unit that can the aminating alkoxylated polyol of quaternized partially or completely negatively charged ion.In one embodiment, described quaternized be that part is quaternized.In another embodiment, described quaternized be quaternized fully.The quaternized of the unitary nitrogen of amine end-blocking can be partially or completely quaternized, and be preferably quaternized fully.Non-limiting synthetic schemes is illustrated among following the synthetic schemes I and synthetic schemes II:
The aminating alkoxylated polyol of synthetic schemes I negatively charged ion
Described method can comprise optional step 1, step 2 and optional step 3 and 4.Should be noted that described step by with an amine end-blocking unit to the nucleophilic substitution of sulphate moiety to provide negatively charged ion aminating alkoxylated polyol.This is non-limiting embodiment, because phosphoric acid salt or carbonate group also can be used for being replaced by amine end-blocking unit.
Synthetic schemes II:
Scheme II is different from scheme I:(1 aspect two) use metal catalyst and hydrogen to finish the direct substitution of opposite end hydroxylic moiety by catalyzed oxidation/reduction; (2) by as US6, in 452,035 the amination of disclosed transsulfation and quaternized after carry out sulfation.The zwitter-ion alkoxylated polyol of same combination can be by top scheme I or scheme II preparation.Those skilled in the art will approve and use other amine end-blocking unit to include but not limited to ammonia or dimethylamino propylamine.
The inventive method specific description will be explained below.
The ethoxylation of polyvalent alcohol
The ethoxylation of polyvalent alcohol (for example sorbyl alcohol) can be finished with any known technology, described in EP 174436 A1.The also available known technology of propoxylation and butoxyization is finished.
(17.5g 0.0962mol) joins autoclave, with nitrogen autoclave is purified, and sorbyl alcohol is heated to 110 ℃ to 120 ℃ with sorbyl alcohol; Start autoclave and stir and be evacuated to about 2.6kPa (20mmHg.).
When continuing to vacuumize, autoclave is cooled to about 110 ℃ to 120 ℃, adds the methanol solution (0.0288 mole is loaded with 5% catalyzer that reaches according to hydroxylic moiety) of 25% sodium methylate of 6.2g simultaneously.Remove under the vacuum in the autoclave from the methyl alcohol in the methylate solution.Using appts is monitored the power that agitator consumes.Agitator power is synthermal monitors together with pressure.When removing methyl alcohol from autoclave, agitator power and temperature value raise gradually, and the increase of the viscosity of mixture, and viscosity kept the most of methyl alcohol of stable sign to be removed in about 1.5 hours.Add heat under the vacuum again and stirred the mixture 30 minutes.
Remove vacuum, and the cooling autoclave or keep its in 110 ℃ with autoclave with nitrogen be charged to 1725kPa (250psia) then emptying to environmental stress.With nitrogen autoclave is charged to 1380kPa (200psia).Oxyethane progressively is charged to autoclave, when carefully monitoring autoclave pressure, temperature and ethylene oxide flow rate, remains on temperature between 110 ℃ and 120 ℃ and limit the temperature that any because exothermic heat of reaction causes and raise.After charging into the oxyethane of 483g (10.97mol forms every mole OH 19 moles oxyethane altogether), temperature is risen to 120 ℃ and with mixture restir 2 hours.
Then reaction mixture is collected in the 22L three neck round-bottomed flasks that purified with nitrogen.Heating (110 ℃) down passes through slowly to add 2.8g methylsulfonic acid (0.00288 mole) with alkali catalyst neutralization and mechanical stirring.Then reaction mixture is removed remaining oxyethane and in mixture, sprayed rare gas element (argon or nitrogen) by the gas dispersion glaze and come deodorizing, stir simultaneously and heated mixt to 120 ℃ a hour.The final reacting product of about 500g is cooled off a little, and pour into and use in the Glass Containers of nitrogen purge so that preserve.
Alternatively, can buy required or be lower than the polyvalent alcohol of required degree of alkoxylation, for example, CAS 52625-13-5 is available from propoxylation sorbyl alcohol or the sorbitol polyoxyethylene ether of Lipo Chemicals Inc..Wherein required degree of alkoxylation obtains by known and/or above-mentioned method.
Sorbyl alcohol EO
114The sulfation of (on average 19 EO parts of each hydroxylic moiety)
In a 500mL Erlenmeyer flask, be weighed into sorbyl alcohol E
114(299.7g, 0.058mol) and methylene dichloride (300g) (" described solution ").Loading onto the magnetic splash bar for this flask also stirs until dissolving fully.Place ice bath to described solution to reach about 10 ℃ in flask.(48.3g, vigorous stirring in the time of 0.415mol) is to form reaction soln slowly to pour chlorsulfonic acid into about 5 minutes time.Stirring reaction solution is 1.5 hours in ice bath.
The solution of the 50g methylene dichloride of sodium methylate (25% methanol solution of 197g) is placed 1L Erlenmeyer flask (" alkaline solution ") and reaches about 10 ℃ in the ice bath cooling until the temperature of solution.With this alkaline solution of magnetic splash bar vigorous stirring.Reaction soln is slowly poured in the alkaline solution with about 3 minutes time.Can be observed gentle heat release.Gained solution is because the formation of salt becomes emulsus.After adding, recording the pH value is about 12.In this gained solution, add the distilled water of about 100mL, and the gained emulsion is transferred in the round-bottomed flask of a 1L, and use Rotary Evaporators a part of to obtain settled solution 50 ℃ of evaporations.This settled solution is transferred to Kulgelrohr equipment.Under 60 ℃ and 133Pa (1mm Hg), evaporate this solution to obtain the canescence waxy solid of 366g, 90% activity (10% salt).
Carbon NMR composes (500MHz; Pulse sequence: s2pul, solvent D
2O; Relaxation delay 0.300 second, pulse 45.0; Acquisition time 1.090 seconds) show do not have alcohol groups and new peak occurs at about 67ppm at about 60ppm, end group vitriol is consistent with forming.Proton N MR composes (500MHz or 300MHz; Pulse sequence: s2pul, solvent D
2O; Relaxation delay 1.000 seconds, pulse 45.0; Acquisition time 2.345 seconds) show new peak at about 4ppm, its integration with oppose at the oxyethyl group proton of about 3.5ppm, and consistent with molecule with 6 end group vitriol.
Embodiment 2: the sorbyl alcohol EO of embodiment 1
114The amination of six vitriol
Glass bushing pipe to 200mL is weighed into sorbyl alcohol EO
114Six vitriol (90% active substance of 61.3g, 0.0095mol) and 3-(dimethylamino) propylamine (" DMAPA " 18.5g, 0.181mol).Under 152kPa (150psig) nitrogen, reach 165 and kept 2 hours until temperature waving autoclave internal heating bushing pipe 165.Be cooled to room temperature (20 ℃ to 25 ℃).With 150mL dichloromethane extract matter, and centrifugal to isolating salt.The round-bottomed flask that supernatant liquor is transferred to a 500mL also is removed at the solvents of 50 ℃ of described supernatant liquors of evaporation to great majority (less than 5mL) with Rotary Evaporators.Heat 30 minutes to removing excessive amine with Kugelrohr equipment at 120 ℃ and 133Pa (1mmHg) time to obtain the brown hard solid of 47.8g.Proton N MR (500MHz or 300MHz; Pulse sequence: s2pul, solvent D
2O; Relaxation delay 0.300 second, pulse 45.0; Acquisition time 3.744 seconds) shows about 3 vitriol of each molecule and about 2 DMAPA.
Embodiment 3: embodiment 2 contains the quaternized of amine vitriol
Be equipped with in the round-bottomed flask of magnetic stirring bar, at a 500mL aminating sorbyl alcohol EO
114Be dissolved in the methylene dichloride of 100g, and be cooled to temperature with ice bath and reach 10 ℃.With sodium methylate (25% methanol solution) regulator solution to pH value is 12.In solution, add methyl iodide (15.0g, 0.106mol).Clog flask and solution stirring is spent the night (about 14 hours).Evaporate this solution to obtain the brown solid that is clamminess of 66g with Kugelrohr equipment at 50 ℃ and 133Pa (1mmHg) time.Proton N MR (500MHz or 300MHz; Pulse sequence: s2pul, solvent D
2O; Relaxation delay 1.000 seconds, pulse 45.0, acquisition time 2.345 seconds) show that the nitrogen quilt in all amine end-blocking unit is quaternized fully.
Cleaning compositions
The invention still further relates to the cleaning compositions of the alkoxylated polyol compounds that comprises modification of the present invention.These cleaning compositions can be any conventionally forms, be liquid, powder, particle, agglomerate, paste, tablet, pouch, bar, gel, the type of sending with two Compartment comtainers, spraying or foam shampoo, pre-wetting cleaning piece (promptly, described cleaning compositions combines with nonwoven material, US 6 as people such as Mackey, 121, the sort of described in 165), by human consumer's water activatory dry wipe (promptly, described cleaning compositions combines with nonwoven material, US 5 as people such as Fowler, the sort of described in 980,931), uniform or heterogenetic human consumer cleaning product form with other.
Except cleaning compositions, compound of the present invention also applicable to or mix in the industrial cleaners (being floor cleaner).Usually these cleaning compositions also comprise tensio-active agent and other cleaning ancillary component in addition, will discuss in more detail below.In one embodiment, cleaning compositions of the present invention is the liquid or solid laundry detergent composition.
In another embodiment, cleaning compositions of the present invention is a hard surface cleaning composition, and preferred wherein said hard surface cleaning composition soaks into nonwoven material matrix." soaking into " used herein is meant that described hard surface cleaning composition is placed in nonwoven material matrix and contacts, make described hard surface cleaning composition infiltrate in the described nonwoven material matrix of at least a portion, preferred described hard surface cleaning composition makes described nonwoven material matrix saturated.
In another embodiment, described cleaning compositions is the liquid dish cleaning compositions, as the form of liquid hand dishwashing composition, solid automatic tableware washing cleaning compositions, liquid automatic tableware washing cleaning compositions and automatic tableware washing cleaning compositions small pieces/dosage unit.
Described cleaning compositions also can be used for the car care composition, is used to clean various surfaces such as hardwood, ceramic tile, pottery, plastics, leather, metal, glass.This cleaning compositions also can be designed for personal care composition such as shampoo Compositions, bath shampoo, liquid or solid soap and other cleaning compositions (wherein, tensio-active agent can with not fixedly the hardness face contact), and in all compositions, need the surfactant system of anti-the scale of hardness, as the oil drilling composition.The alkoxylated polyol compounds of modification
Cleaning compositions of the present invention can comprise the polyol compound by the modification as described herein of the weight of described cleaning compositions about 0.005% to about 30% and for example about 0.01% to about 10% and for example about 0.05% to about 5%.
Tensio-active agent-cleaning compositions of the present invention can comprise tensio-active agent or surfactant system (comprising the tensio-active agent that is selected from nonionic, negatively charged ion, positively charged ion, both sexes, zwitter-ion, semi-polar nonionic surfactants); With other auxiliary agent for example alkyl alcohol or their mixture.Cleaning compositions of the present invention also comprises by the weight of described cleaning compositions about 0.01% to about 90%, for example about 0.01% to about 80%, for example about 0.05% to about 50% and for example about 0.05% to about 40% the surfactant system that contains one or more tensio-active agents.
Anion surfactant
The non-limiting example that can be used for anion surfactant of the present invention comprises: C
8-C
18Alkylbenzene sulfonate (LAS); C
10-C
20The primary, side chain and random alkyl-sulphate (AS); C
10-C
18Secondary (2,3) alkyl-sulphate; C
10-C
18Alkyl alkoxy sulfate (AE
xS), wherein x is 1 to 30; The C that comprises 1 to 5 ethoxy unit
10-C
18The alkyl alkoxy carboxylate salt; US 6,020, and 303 and US 6,060, the medium chain branched-chain alkyl vitriol described in 443; US6,008,181 and US 6,020, the medium chain branched-chain alkyl alkoxy sulfate described in 303; Modified alkylbenzene sulfonates (MLAS) described in WO 99/05243, WO 99/05242 and the WO 99/05244; Methyl ester sulfonate (MES); And sulfonated (AOS).
Nonionogenic tenside
The non-limiting example of nonionogenic tenside comprises: C
12-C
18Alkylethoxylate is as the NEODOL available from Shell
Nonionogenic tenside; C
6-C
12Alkyl phenolic alkoxy thing, wherein said alcoxylates unit are vinyloxy group and the unitary mixture of propenyloxy group; C
12-C
18Pure and mild C
6-C
12The condenses of alkylphenol and ethylene oxide/propylene oxide block alkyl polyamine ethoxylate is as the PLURONIC available from BASF
C
14-C
22The medium chain branched-chain alcoho, as US 6,150, the BA that discusses in 322; C
14-C
22Medium chain branched-chain alkyl alcoxylates, BAE
x, wherein x is 1 to 30, as US 6,153, and 577, US 6,020,303 and US 6,093, described in 856; As the U.S.4 of the Llenado that announced on January 26th, 1986, the alkyl polysaccharide described in 565,647; Particularly as US 4,483,780 and US4, the alkyl polyglycoside described in 483,779; As US 5,332, the polyhydroxy fatty acid amide described in 528 (GS-yl); With as US 6,482,994 and WO 01/42408 described in ether capped poly-(alkoxylate) pure tensio-active agent.
Cats product
The non-limiting example of cats product comprises: can have the quaternary ammonium surfactant of maximum 26 carbon atoms, it comprises: as US 6,136, and alkoxy quaternary ammonium (AQA) tensio-active agent of discussing in 769; As 6,004, the dimethyl hydroxyethyl quaternary ammonium of discussing in 922; As the polyamine cationic tensio-active agent of discussing among WO 98/35002, WO 98/35003, WO 98/35004, WO 98/35005 and the WO 98/35006; As United States Patent (USP) 4,228,042,4,239,660,4,260,529 and US 6,022,844 in the cationic ester tensio-active agent discussed; And the amino surface promoting agent of discussing among US 6,221,825 and the WO 00/47708, specifically, be amido propyl-dimethyl amine (APA).
Zwitterionics
The non-limiting example of zwitterionics comprises: the derivative of secondary amine and tertiary amines derived thing, heterocyclic secondary and tertiary amines derived thing or quaternary ammonium, season or uncle's sulfonium compound.The embodiment of zwitterionics is referring to the United States Patent (USP) of announcing on December 30th, 1,975 3,929,678 of authorizing people such as Laughlin, and the 19th hurdle the 38th walks to the 22nd hurdle the 48th row; Trimethyl-glycine, it comprises alkyl dimethyl trimethyl-glycine and coco dimethyl amido propyl betaine, C
8To C
18(C
12To C
18) amine oxide and sulfo group and hydroxyl trimethyl-glycine, as N-alkyl-N, N-dimethylamino-1-propanesulfonic acid salt, wherein alkyl can be C
8To C
18, C
10To C
14
Amphoterics
The non-limiting example of amphoterics comprises: the aliphatic derivatives of secondary amine or tertiary amine, or the aliphatic derivatives of heterocyclic secondary and tertiary amine, wherein aliphatic group can be straight or branched.Aliphatic substituting group comprises at least about 8 carbon atoms, typical case about 8 to about 18 carbon atoms, and at least one comprises water lyotropy anionic group, as carboxyl, sulfonate radical, sulfate radical.The embodiment of amphoterics is referring to the 19th hurdle in the United States Patent (USP) of announcing on December 30th, 1,975 3,929,678 of authorizing people such as Laughlin, and the 18th walks to the 35th row.
Semi-polar nonionic surfactants
The non-limiting example of semi-polar nonionic surfactants comprises: water-soluble amine oxides, and it comprises one about 10 and is selected from alkyl and comprises about 1 to about 3 carbon atom hydroxyalkyl parts to the moieties of about 18 carbon atoms and two; The water soluble oxidized phosphine, it comprises one about 10 and is selected from alkyl and comprises about 1 to about 3 carbon atom hydroxyalkyl parts to the moieties of about 18 carbon atoms and two; And water-soluble sulfoxide, it comprises one about 10 to about 18 carbon atom alkyls part and is selected from alkyl and comprises about 1 to about 3 carbon atom hydroxyalkyl parts.Referring to WO 01/32816, US 4,681,704 and US 4,133,779.
Gemini surface active agent
Propose, Gemini surface active agent is the compound that has at least two hydrophobic groups and at least two hydrophilic radicals in each molecule.These are called as " Gemini surface active agent " in the literature, as " Chemtech " in March, 1993, " the J.American Chemical Soc. " of the 30th page to the 33rd page and 1993, the 115th volume, the 10083rd page to the 10090th page, and the reference of wherein being quoted.
The cleaning subsidiary material
Usually, cleaning additive be with comprise only have indivisible must composition cleaning compositions be transformed into be used to wash, the needed any material of cleaning compositions of hard surface, personal care, human consumer, commerce and/or industry cleaning purposes.In certain embodiments, cleaning additive, especially for the human consumer directly uses the feature of the cleaning product that designs at home environment and is easy to be generally acknowledged by those skilled in the art as the actual characteristic of cleaning product.
The definite character of these annexing ingredients and the content that mixes thereof will depend on the physical form of described cleaning compositions and the character of using its clean operation that carries out.
If share with SYNTHETIC OPTICAL WHITNER, this cleaning additive composition will have satisfactory stability thereupon.According to the needs of rules, some embodiment of this paper cleaning compositions should not conform to boron and/or not phosphorous hydrochlorate.The content of cleaning additive counts about 0.00001% to about 99.9% and for example about 0.0001% to about 50% by the weight of described cleaning compositions.The usage quantity of total cleaning compositions can be according to the purposes of expection and wide variation, for example the several ppm from solution to so-called " directly using " pure cleaning compositions in surface to be cleaned.
Very typically, this paper cleaning compositions such as laundry detergent, clothes washing agent addition agent, hard surface cleaners, synthetic and soap base washing soap blank, fabric softener and fabric treating liquid, solid and multiple treatment articles will need several assistants, though the product of some simple preparation, as bleach additive only needs, for example oxygen bleaching agent and tensio-active agent as herein described.The table look-up of suitable washing or cleaning subsidiary material can be referring to WO 99/05242.
Common cleaning additive comprises (not comprising any material that has above defined) such as washing assistant, enzyme, the polymkeric substance that does not above have to discuss, SYNTHETIC OPTICAL WHITNER, bleach-activating agent, catalytic materials.Other cleaning additive of this paper can comprise suds booster, suds suppressor (defoamer) etc., except that above-mentioned those various activeconstituentss or dedicated substances such as dispersed polymeres (for example, available from BASFCorp. or Rohm ﹠amp; Haas), color spot agent, silverware protective material, antirust and/or inhibitor, dyestuff, weighting agent, sterilant, basicity source, hydrotropic agent, antioxidant, enzyme stabilizers, preceding spices, spices, solubilizing agent, carrier, processing aid, pigment; and, comprise solvent, sequestrant, dye transfer inhibitor, dispersion agent, whitening agent, suds suppressor, dyestuff, structural elasticity agent, fabric softener, anti scuffing agent, hydrotropic agent, processing aid and other fabric care agent, surface and skin-care agent for liquid preparation.The suitable embodiment of other these cleaning additives and consumption also is present in United States Patent (USP) 5,576, and 282,6,306,812 B1 and 6,326 are among 348 B1.
Using method
The present invention includes the method for clean surface or fabric.This method may further comprise the steps: with pure form or with the alkoxylated polyol compounds of the modification of the present invention of washing liq dilution, or the embodiment of cleaning compositions that comprises the alkoxylated polyol compounds of modification of the present invention contacts with at least a portion of surface or fabric, and randomly rinsing should surface or fabric then.Preferably, make described surface or fabric before above-mentioned optional rinse step, carry out washing step.For the present invention, washing includes but not limited to clean and mechanical stirring.
As those skilled in the art's approval, cleaning compositions of the present invention ideally is applicable to care and household (hard surface cleaning composition), personal care and/or washing application.Therefore, the present invention includes the method that is used for clean surface and/or laundering of textile fabrics.This method may further comprise the steps: with the alkoxylated polyol compounds of modification or comprise the surface and/or the fabric of cleaning compositions contact need cleaning/washing of the alkoxylated polyol compounds of modification.This surface can be included in the most of any hard surface that exists in the typical household, as hardwood, ceramic tile, pottery, plastics, leather, metal, glass, maybe can be included in the clean surface among the personal care product, as hair and skin.This surface also can comprise dish, glass and other cooking surface.Fabric can comprise any fabric that great majority can wash under the normal consumer working conditions.
The pH that selects described cleaning compositions solution is needing to be suitable for clean Surface to greatest extent, and can crossing over widely, the pH scope is about 5 to about 11.For personal care such as skin and hair cleaning, it is about 5 to about 8 that the pH of said composition preferably has pH, and for the washing cleaning compositions, pH is about 8 to about 10.The strength of solution that described composition preferably uses for about 200ppm to about 10,000ppm.Water temperature is preferably about 5 ℃ to about 100 ℃.
To being used to wash cleaning compositions, the solution that described composition preferably uses (or washing liq) concentration is that about 200ppm is to about 10000ppm.Water temperature is preferably about 5 ℃ to about 60 ℃.Water is preferably about 1: 1 to about 20: 1 with the ratio of fabric.
The present invention includes the method for clean surface or fabric.This method may further comprise the steps: contact is soaked into and the nonwoven material of cleaning compositions embodiment of the present invention matrix is arranged and contact at least a portion surface and/or fabric with described nonwoven material matrix.Described method also can comprise washing step.For the present invention, washing includes but not limited to clean and mechanical stirring.Described method also can comprise rinse step.
" nonwoven material matrix " used herein can comprise any have suitable quantitatively, the conventional pattern non-woven material slice or the fibrous reticulum of thickness (thick), absorptivity and strength characteristics.Suitable commercially available nonwoven material matrix embodiment comprises by DuPont with trade(brand)name SONTARA
With by James River Corp. with trade(brand)name POLYWEB
Those that sell.
Approve that as those skilled in the art cleaning compositions of the present invention is ideally suited for the hard surface purposes.Therefore, the present invention includes the method for cleaning hard surfaces.Said method comprising the steps of: with hard surface solution or soak into and have the nonwoven material of cleaning compositions embodiment of the present invention matrix to contact hard surface to be cleaned.These using method may further comprise the steps: contact at least a portion nonwoven material matrix with cleaning compositions, then with user's hand or by using a nonwoven material matrix connection and the tool in contact hard surface on it.
Approve that as those skilled in the art cleaning compositions of the present invention is ideally suited for the liquid dish cleaning compositions.Use liquid dish method for compositions of the present invention may further comprise the steps: with dirty dish and significant quantity, typically about 0.5mL contacts to the liquid dish cleaning compositions of the present invention that is diluted in the water of about 20mL (per 25 pending dish).Suitable embodiment is found in following table 5.
Usually, about 0.01mL to the liquid dish cleaning compositions of the present invention of about 150mL have volume about 1000mL extremely in the tank of about 20000mL scope with about 2000mL extremely the water of about 20000mL mix.Dirty dish is immersed the sink that comprises diluted composition, realize cleaning them with a dishcloth, sponge or the dirty face of similar articles contact dish then.Can with this a dishcloth, sponge or similar articles with immerse in the mixture of detergent composition and water before dish surface contacts, typically contact for some time then with dish surface, this time about 1 to the scope in about 10 seconds.The shampooing of the simultaneous dish surface of preferred a dishcloth, sponge or similar articles contact dish surface.
Another using method comprises in the dirty water-bath of dish immersion without any the liquid dish cleaning compositions.To be used to absorb the device of liquid dish cleaning compositions, for example sponge directly places undiluted liquid dish cleaning compositions for some time of independent amount, this time typically about 1 to about 5 seconds scope.Then will absorb utensil and contact the surface of each dirty dish independently to remove described dirt with therefore undiluted liquid dish cleaning compositions.This absorption utensil typically contacts each dirty dish surface for some time, this time about 1 to about 10 seconds scope.The simultaneous shampooing of preferred absorbers tool contact dish surface.
Approve that as those skilled in the art cleaning compositions of the present invention is applicable to that also the personal cleanliness nurses purposes.Therefore, the present invention includes the method for cleaning skin or hair.Said method comprising the steps of: with cleaning soln or soak into and have the nonwoven material of cleaning compositions embodiment as herein described matrix to contact skin/hair to be cleaned.When contact skin and hair, the using method of nonwoven material matrix can be with user's hand or the instrument by using a nonwoven material matrix to be connected thereto.
Other composition
Other composition that comprises The compounds of this invention can be used for personal care composition, as contact lens solutions, as tackiness agent, be used for rubber sulfuration, be used for the urethane technological process, be used for dye composite, as composition for ink, as the dispersion agent of agricultural application, as the antifungal composition dispersion agent in other composition.
Preparation
Table 1-liquid scrubbing cleaning compositions
| A | |
| Composition | [weight percent %] |
| Linear alkylbenzene sulfonate | 10-15 |
| C 12-15Alcohol ethoxy ( 1.1-2.5) vitriol | 1-5 |
| C 12-13Alcohol ethoxylate ( 7-9) | 1-5 |
| The coco dimethyl amine oxide | 0.1-1 |
| Lipid acid | 1-5 |
| Citric acid | 1-5 |
| Polymkeric substance c 1 | 0.5-3 |
| Hydroxylation Viscotrol C (configuration agent) | 5-20 |
| Water, spices, dyestuff and other trace components | Add to 100 |
As embodiment 1 to 3 and should be with Formula I any one described polymkeric substance to the IV.
The washing cleaning compositions of the low effervescent granules shape of table 2
| B | C | D | |
| Weight percent (%) | Weight percent (%) | Weight percent (%) | |
| C 11-12The alkylbenzene sulfonate of straight chain | 7 | 5.1 | 10.2 |
| C 12-18 (butter)Alkyl-sulphate | 1 | 1 | 1 |
| C 14-15Alkylethoxylate (EO=7) | 3.2 | 3.2 | 3.2 |
| APA 1 | 0.94 | 0.68 | 1.36 |
| Silicate-like builder 2 | 4.05 | - | - |
| Zeolite A 3 | 16.65 | - | - |
| Carbonate 4 | 14.04 | - | - |
| Citric acid (anhydrous) | 2.93 | 2.93 | 2.93 |
| Vinylformic acid/maleic acid 5 | 0.97 | 0.97 | 0.97 |
| Polymkeric substance 6 | 1-5 | 1-5 | 1-5 |
| Percarbonate | 12.8 | 16.18 | 13.25 |
| Tetra acetyl ethylene diamine | 3.64 | 5.92 | 3.95 |
| 1-hydroxyl vinylidene-1, the 1-di 2 ethylhexyl phosphonic acid | 0.18 | 0.18 | 0.18 |
| S, S-(1-N, N '-disuccinic acid) | 0.2 | 0.2 | 0.2 |
| MgSO 4 | 0.42 | 0.42 | 0.42 |
| Enzyme 7(% particle) | 1.26 | 1.26 | 1.26 |
| Minor component (spices, dyestuff, suds-stabilizing agent) | Add to 100 | Add to 100 | Add to 100 |
1C
8-10The amido propyl dimethyl amine
2Amorphous water glass (SiO
2: Na
2O; 2.0 ratio)
3The sodium silicoaluminate hydrate,
Chemical formula Na
12(AlO
2SiO
2)
12Have the 27H of main granularity in 0.1 to 10 micrometer range
2O
4Have the anhydrous sodium carbonate of granularity between 200 μ m and 900 μ m
54: 1 vinylformic acid/toxilic acids, molecular-weight average about 70,000 or 6: 4 vinylformic acid/toxilic acids, molecular-weight average are about 10,000)
6As embodiment 1 to 3 and any one described polymkeric substance of formula I to IV of the present invention
7One or more enzymes, as:
Proteolytic enzyme-protease has 3.3% organized enzyme by weight, by NOVOIndustries A/S with trade(brand)name SAVINASE
Sell; Protease has 4% organized enzyme by weight, described in WO 95/10591, is sold by Genencor Int.Inc..
Sumizyme MP-protease has 5.3% organized enzyme by weight, is sold by NOVO Industries A/S.
Cellulase-fibrinolytic enzyme has 0.23% organized enzyme by weight, is sold with trade(brand)name Carezyme by NOVOIndustries A/S.
Amylase-amylolytic enzyme has 1.6% organized enzyme by weight, by NOVOIndustries A/S with trade(brand)name TERMAMYL 120T
Sell; Amylolytic enzyme is described in PCT/US9703635.Lipase-lipolytic enzyme has 2.0% organized enzyme by weight, by NOVO Industries A/S with trade(brand)name LIPOLASE
Sell; Lipolytic enzyme has 2.0% organized enzyme by weight, by NOVO Industries A/S with trade(brand)name LIPOLASE ULTRA
Sell.
Hydratase, phosphoenolpyruvate-endo-dextranase has 1.5% organized enzyme by weight, is sold by NOVOIndustries A/S.
The granular washing cleaning compositions of table 3
Table 3 (continuing)
| E | F | G | H | |
| Weight percent (%) | Weight percent (%) | Weight percent (%) | Weight percent (%) | |
| C 10-12Linear alkyl benzene sulphonic acid | 13.4-15.0 | 15.2-17.2 | 12.7 | 12.7 |
| C 12-14Alkylethoxylate (EO=9) | 2.8 | 2.8 | 3.0 | 3.0 |
| Washing assistant 1 | 18 | -- | -- | -- |
| Sequestering agent 2 | -- | 17 | -- | -- |
| Enzyme | 0.35 | 0.40 | -- | -- |
| Polymkeric substance 3 | 1-2 | 1-2 | 1 | 1 |
| Carboxymethyl cellulose | 0.2 | 0.2 | 0.5 | -- |
| Suds suppressor 4 | 0.01 | 0.01 | -- | -- |
| Polyacrylic ester 5 | 0.80 | 0.8 | 0.5 | |
| Damping fluid | 4.0 | 2.0 | 6.0 | 6.0 |
| Carbonate | 11.0 | 15.0 | 8.0 | 8.0 |
| Whitening agent | 0.08 | 0.08 | 0.03 | 0.03 |
| Sodium sulfate | 34.83 | 32.33 | 65.09 | 65.09 |
| Water and minor component | Add to 100 | Add to 100 | Add to 100 | Add to 100 |
1Tripoly phosphate sodium STPP
2Zeolite A: sodium silicoaluminate hydrate, molecular formula are Na
12(AlO
2SiO
2)
12Have the 27H of main granularity in 0.1 to 10 micrometer range
2O
3As embodiment 1 to 3 and should be with the alkoxylated polyol compounds of Formula I to the described modification of IV
4Suds suppressor
5Mw=4500 table 4 hard surface cleaning composition
| Floor-cleaning polishing solution I | Floor-cleaning solution J | |
| Weight percent (%) | Weight percent (%) | |
| C 11Alcohol ethoxylate (EO=5) | 0.03 | 0.03 |
| C 8Sodium sulfonate | 0.01 | 0.01 |
| Propylene glycol n-butyl ether | 2 | 2 |
| The 2-phenoxyethyl alcohol | 0.05 | 0.05 |
| Ethanol | 3 | |
| Polymkeric substance 1 | 0.015 | 0.015 |
| 2-dimethylamino-2-methyl-2-propyl alcohol (DMAMP) | 0.01 | 0.01 |
| Spices | 0.01-0.06 | 0.01-0.06 |
| Suds suppressor 2 | 0.003 | 0.003 |
| 2-methyl-4-isothiazoline-3-ketone+chlorinated derivative | 0.015 | -- |
| Water and minor component | Add to 100 | Add to 100 |
1As embodiment 1 to 3 and should be with Formula I to the described polymkeric substance of IV.
2As Dow Corning AF emulsion or polydimethylsiloxane table 5 liquid dish cleaning compositions
| K | L | M | |
| C 12-13Alcohol ethoxylate vitriol EO=0.6 | 26 | 23 | 24 |
| Amine oxide | 5.8 | 5.8 | 5.8 |
| C 8-12Alcohol ethoxylate EO=8 | 2 | 2 | 2 |
| Ethanol | 2 | 2 | 2 |
| The isopropyl benzene sodium sulfonate | 1.80 | 1.80 | 1.80 |
| NaCl | 1.4 | 1.4 | 1.4 |
| MgCl 2 | 0.2 | 0.2 | 0.2 |
| Profoamer 1 | 0.2 | 0.2 | 0.2 |
| Polymkeric substance 2 | 0.8 | 0.8 | 0.8 |
| Water and other trace components (that is, dyestuff, spices, diamines etc.) | Add to 100 | Add to 100 | Add to 100 |
1As US 6,645, described in the 925B1
2As embodiment 1 to 3 and Formula I of the present invention to the described polymkeric substance of IV.
The relevant portion of all documents of quoting in detailed Description Of The Invention is incorporated herein by reference; It is to its approval as prior art of the present invention that the quoting of any document not can be regarded as.
Although illustrated and described specific embodiments of the present invention, it will be apparent to those skilled in the art that many other variations and modifications may be made in the case of without departing from the spirit and scope of protection of the present invention.Therefore, in additional claims, comprise all such changes and modifications in the scope of the invention consciously.
Claims (10)
1. compound, described compound is characterised in that and comprises polyol compound, described polyol compound comprises at least three hydroxylic moieties, in the described hydroxylic moiety at least one also comprises the alkoxyl group part, and described alkoxyl group partly is selected from oxyethyl group, propoxy-, butoxy and their mixture; In the wherein said in addition hydroxylic moiety at least one also comprises negatively charged ion end-blocking unit.
2. compound, described compound is characterised in that and comprises polyol compound, described polyol compound comprises at least three hydroxylic moieties, in the described hydroxylic moiety at least one also comprises the alkoxyl group part, and described alkoxyl group partly is selected from oxyethyl group, propoxy-, butoxy and their mixture; In the wherein said in addition hydroxylic moiety at least one also comprises negatively charged ion end-blocking unit, and in the described hydroxylic moiety at least one replaced by amine end-blocking unit.
3. compound, it is characterized in that comprising polyol compound, described polyol compound comprises at least three hydroxylic moieties, and at least one in the described hydroxylic moiety also comprises the alkoxyl group part, and described alkoxyl group partly is selected from oxyethyl group, propoxy-, butoxy and their mixture; In the wherein said in addition hydroxylic moiety at least one also comprises negatively charged ion end-blocking unit, and in the described hydroxylic moiety at least one replaced by quaternary ammonium end-blocking unit.
4. compound, described compound is characterised in that and comprises polyol compound, described polyol compound comprises at least three hydroxylic moieties, in the described hydroxylic moiety at least one also comprises the alkoxyl group part, and described alkoxyl group partly is selected from oxyethyl group, propoxy-, butoxy and their mixture; In the wherein said in addition hydroxylic moiety at least one also comprises negatively charged ion end-blocking unit, and at least one in the described hydroxylic moiety replaced by amine end-blocking unit, and in the described hydroxylic moiety at least one replaced by quaternary ammonium end-blocking unit.
5. compound as claimed in claim 1, wherein said hydroxylic moiety comprises the alkoxyl group part, and the average degree of alkoxylation of each hydroxylic moiety that described alkoxyl group partly comprises is 1 to 100.
6. as each described compound in the claim 1 to 5, at least one in the wherein said negatively charged ion end-blocking unit replaced by amine end-blocking unit.
7. as each described compound in claim 2 or 4, wherein said amine end-blocking unit is selected from ammonia, methylamine, dimethylamine, 1, the 2-quadrol, dimethylamino propylamine, two dimethylamino propylamines (two DMAPA), hexanediamine, ethamine, diethylamine, lauryl amine, benzylamine, polymine, isoquinoline 99.9, the butter triethylenediamine, monobasic monoamine, monobasic diamines, monobasic polyamines, dibasic monoamine, dibasic diamines, dibasic polyamines, trisubstituted triamine, trisubstituted polyamines, comprise polysubstituted polyamines more than three replacements, precondition is that at least one nitrogen comprises a hydrogen, and their mixture.
8. as each described compound in the claim 1,2,3 or 4, wherein said polyol compound is derived from sugar or reducing sugar monomer, and described sugar or reducing sugar monomer are selected from: glucose, maltose, trisaccharide maltose, Fructus Hordei Germinatus pentose, Fructus Hordei Germinatus hexose, sorbyl alcohol, maltose alcohol, sucrose, Xylitol, glycerine, glycerol derivative, Polyglycerine, tetramethylolmethane, polyvinyl alcohol, xylan, reductive trisaccharide maltose, reductive Star Dri 5 and their mixture.
9. the cleaning compositions of an inclusion compound, described compound is characterised in that and comprises as each described compound in the claim 1,2,3 or 4.
10. cleaning compositions as claimed in claim 18, wherein said cleaning compositions also comprises surfactant, described tensio-active agent are selected from negatively charged ion, nonionic, positively charged ion, zwitter-ion, amphoterics and their mixture.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53138503P | 2003-12-19 | 2003-12-19 | |
| US60/531,385 | 2003-12-19 | ||
| PCT/US2004/043074 WO2005063847A1 (en) | 2003-12-19 | 2004-12-17 | Modified alkoxylated polyol compounds |
Publications (2)
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| CN1894305A true CN1894305A (en) | 2007-01-10 |
| CN1894305B CN1894305B (en) | 2010-10-13 |
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| CN2004800378221A Expired - Fee Related CN1894305B (en) | 2003-12-19 | 2004-12-17 | Modified alkoxylated polyol compounds |
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| EP (1) | EP1694741A1 (en) |
| JP (1) | JP2007520459A (en) |
| CN (1) | CN1894305B (en) |
| AR (1) | AR047292A1 (en) |
| BR (1) | BRPI0417536A (en) |
| CA (1) | CA2549571A1 (en) |
| MX (1) | MXPA06007020A (en) |
| WO (1) | WO2005063847A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105732442A (en) * | 2016-01-27 | 2016-07-06 | 江苏苏博特新材料股份有限公司 | Oligomer surfactant, and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101084297A (en) * | 2004-12-17 | 2007-12-05 | 宝洁公司 | Hydrophobically modified polyols for improved hydrophobic soil cleaning |
| EP1838825A1 (en) | 2004-12-17 | 2007-10-03 | The Procter and Gamble Company | Hydrophilically modified polyols for improved hydrophobic soil cleaning |
| 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 |
| WO2007144819A1 (en) | 2006-06-12 | 2007-12-21 | The Procter & Gamble Company | A lotioned wipe product comprising an anti-stick agent and a performance enhancing agent |
| US8093352B2 (en) | 2008-08-05 | 2012-01-10 | Alcon Research, Ltd. | Polyalkylene oxide polyquaternary ammonium biocides |
| FR3111901B1 (en) * | 2020-06-30 | 2023-02-17 | Arkema France | IMPROVED ALCOXYLATION PROCESS |
| IL302230A (en) * | 2020-10-19 | 2023-06-01 | Oxiteno S A Ind?Stria E Com?Rcio | Composition, agrochemical formulation, methods for increasing water and nutrient availability and for improving pest control in plants and seeds, and the agrochemical formulation |
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| JPS591784A (en) * | 1982-06-24 | 1984-01-07 | 東邦化学工業株式会社 | Dyeing aid for polyester fiber or polyester/cellulose fiber blended mixture |
| NO165797C (en) * | 1985-01-03 | 1991-04-10 | Berol Kemi Ab | SURFACE ACTIVE COMPOUND AND EMULSION CONTAINING THIS, AND USE THEREOF. |
| DE3633421C1 (en) * | 1986-10-01 | 1987-07-23 | Goldschmidt Ag Th | Polyoxyalkylene ethers containing hydroxyl and sulfonate groups and their use in the production of dispersible polyurethanes |
| JPH06306041A (en) * | 1993-04-23 | 1994-11-01 | Kao Corp | Monoglyceride disulfate salt and production of monoglyceride sulfate containing the disulfate salt |
| EP0638685B1 (en) * | 1993-08-10 | 1998-12-23 | Ciba SC Holding AG | Welling agent for mercerising |
| 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 (en) * | 1994-11-21 | 1996-05-23 | Huels Chemische Werke Ag | Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on di, oligo or polyol ethers |
| 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 (en) * | 1996-03-19 | 1997-09-22 | Kao Corp | Production of n-alkylamidoalkanol sulfuric acid ester salt |
| JPH10279553A (en) * | 1997-04-03 | 1998-10-20 | Lion Corp | Production of (poly)glyceryl ether sulfate salt |
| JP2001097942A (en) * | 1999-09-28 | 2001-04-10 | Kao Corp | Method for preparing monoglyceride sulfate |
| JP4208462B2 (en) * | 2000-12-28 | 2009-01-14 | 株式会社Ａｄｅｋａ | Surfactant |
| US6602839B2 (en) * | 2001-01-05 | 2003-08-05 | Huntsman Petrochemical Corporation | Advanced sulfosuccinamate surfactants |
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2004
- 2004-12-17 CN CN2004800378221A patent/CN1894305B/en not_active Expired - Fee Related
- 2004-12-17 CA CA002549571A patent/CA2549571A1/en not_active Abandoned
- 2004-12-17 BR BRPI0417536-0A patent/BRPI0417536A/en not_active IP Right Cessation
- 2004-12-17 AR ARP040104762 patent/AR047292A1/en unknown
- 2004-12-17 MX MXPA06007020A patent/MXPA06007020A/en active IP Right Grant
- 2004-12-17 JP JP2006544144A patent/JP2007520459A/en active Pending
- 2004-12-17 WO PCT/US2004/043074 patent/WO2005063847A1/en not_active Application Discontinuation
- 2004-12-17 EP EP04815188A patent/EP1694741A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105732442A (en) * | 2016-01-27 | 2016-07-06 | 江苏苏博特新材料股份有限公司 | Oligomer surfactant, and preparation method and application thereof |
| CN105732442B (en) * | 2016-01-27 | 2017-11-03 | 江苏苏博特新材料股份有限公司 | Oligomeric-type surfactant, its preparation method and application |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2549571A1 (en) | 2005-07-14 |
| BRPI0417536A (en) | 2007-03-27 |
| MXPA06007020A (en) | 2006-08-31 |
| EP1694741A1 (en) | 2006-08-30 |
| JP2007520459A (en) | 2007-07-26 |
| WO2005063847A1 (en) | 2005-07-14 |
| AR047292A1 (en) | 2006-01-11 |
| CN1894305B (en) | 2010-10-13 |
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