CN101668728A - Novel alkoxylate-containing compositions - Google Patents
Novel alkoxylate-containing compositions Download PDFInfo
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- CN101668728A CN101668728A CN200880013819A CN200880013819A CN101668728A CN 101668728 A CN101668728 A CN 101668728A CN 200880013819 A CN200880013819 A CN 200880013819A CN 200880013819 A CN200880013819 A CN 200880013819A CN 101668728 A CN101668728 A CN 101668728A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/135—Saturated ethers containing hydroxy or O-metal groups having more than one ether bond
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
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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
- C08G65/2609—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 containing aliphatic hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
- C11D1/721—End blocked ethers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Detergent Compositions (AREA)
Abstract
Compositions comprising novel alkylene oxide-extended alkoxylates of a linear or branched 1,3-dialkyloxy-2-propanol are disclosed. In these compositions the alkoxylates may offer a variety of desirable properties, including but not limited to service in formulations as surfactants, detergents, wetting agents, defoam/low foam agents, stabilizers, and the like. The compositions may include productssuch as detergents, pharmaceuticals, paints and coatings, plastics, oilfield chemicals, agricultural agents, and the like.
Description
Background of invention
1. technical field
[0001] the present invention relates to the field of alkoxyl group-ether alcoxylates.More specifically, the present invention relates to use the composition and the method for new alkoxyl group-ether alcoxylates.
2. background technology
[0002], tensio-active agent is used in chemical industry and the production for multiple purpose.These comprise, for example, give wettability and soil release characteristics comprising during wetting agent, emulsifying agent, rinse aid, froth breaking/low infusion, spray cleaner, drug conveying agent, weedicide and sterilant are with emulsifying agent, metal detergent, lacquer, coating, agricultural spreading agent and plant growth agent, the product of latex with stablizer, lacquer and paper conversion and product etc.The glass or plastic containers that one class is often used.It is more insensitive to hard water that nonionogenic tenside is tending towards usually, and compare generation foam still less with the tensio-active agent of some other type, thereby make many defoamers that can be used as in the nonionogenic tenside.Yet unfortunately, many in these tensio-active agents that use at present is alkylphenol based compounds.Recently the alkylphenol based compound is subjected to environmental test, thereby the composition such as preparation and the product that contain them may finally face restriction.
[0003] therefore, need determine to use not composition such as preparation and product in the art based on the nonionogenic tenside of alkylphenol.
Summary of the invention
[0004] therefore, on the one hand in, the invention provides a kind of composition, its comprise straight or branched oxirane expansion 1,3-dialkoxy-2-propyl alcohol alcoxylates.
[0005] in another aspect, the invention provides a kind of preparation method for compositions, described method comprises that 3-dialkoxy-2-propyl alcohol alcoxylates merges in the composition with 1 of the oxirane expansion of straight or branched.
Detailed Description Of The Invention
[0006] composition of the present invention use in many cases various new straight or brancheds, the oxirane expansion 1, any in 3-dialkoxy-2-propyl alcohol alcoxylates is with easy and cost efficient manner preparation.The preparation of alcoxylates is described hereinafter, and be described in detail in temporary patent application (lawyer's recording mechanism (Attorney Docket No) C-65 of common submission, 202P and C-65,205P) in, the full content of described temporary patent application is combined in this by reference.
[0007] raw material at first comprises Epicholorohydrin, is also referred to as 1-chloro-2, the 3-propylene oxide.Skilled in the art will recognize that many commercial source of this material, this material usually can be by the prepared in reaction of propylene and chlorallylene, or for example by the preparation that is converted of multihydroxylated-aliphatic hydrocarbon or its ester to chloro-hydrin(e), this has description in WO 2006020234A1, the full content of the document is combined in this by reference.
[0008] second kind of raw material is an alcohol, and it can be a straight or branched.In some non-limiting embodiments, this alcohol contains 3 to 28 carbon atoms, and in other non-limiting embodiments, it contains 4 to 12 carbon atoms.In particularly preferred embodiments, alkyl chain can comprise 6 to 10 carbon atoms.Alcohol can be primary alconol, secondary alcohol or the tertiary alcohol; Can be saturated or undersaturated; And can randomly contain one or more heteroatomss.For example, in some non-limiting embodiments, suitable selection can comprise renewable raw materials, such as: biological glycerol; 2-Ethylhexyl Alcohol; The NEODOL that some is sold by Shell chemical company
TMBranched-chain alcoho; The EXXAL that some is sold by Exxon-Mobil company
TMBranched-chain alcoho; Their combination; Deng.In other non-limiting embodiments, suitable alcohol can comprise: for example, and ethanol, propyl alcohol, butanols, amylalcohol, hexanol, enanthol, octanol, nonyl alcohol, decyl alcohol, undecyl alcohol, lauryl alcohol, 4-propyl group-1-decanol, 3-butyl-1 nonyl alcohol, 2-methyl-4-propyl group-1-decanol, 3-methyl isophthalic acid-enanthol, 3-methyl-2-enanthol, 3-methyl-3-enanthol, 2-ethyl-1-hexanol, 2-methyl isophthalic acid-enanthol, 2-methyl-1-pentene alcohol, their combination etc.Therefore, in some non-limiting embodiments, can select alcohol to make it contain the part that is selected from the group of forming by following group as its moieties: ethyl, propyl group, butyl, amyl group, hexyl, heptyl, octyl group, nonyl, decyl, undecyl and dodecyl aliphatic cpd; Methyl-, ethyl-, propyl group-and the amyl group of butyl-branching-, hexyl-, heptyl-, octyl group-, nonyl-, decyl-, undecyl-, dodecyl-and tridecyl-aliphatic cpd; Their combination; Deng.In some non-limiting embodiments, alcohol can for, for example, the side chain enanthol, or according to the straight or branched alcohol such as those method preparations of describing in the WO2003024910A1 that transfers Sasol Tech PTY LTD, the full content of the document is combined in this by reference.For example, in some non-limiting embodiments, can select 2-methyl amyl alcohol or 2-isoocanol.
[0009] alcohol can also randomly contain IVA, the VA, VIA and the VIIA family that are selected from the periodic table of elements element as heteroatoms, include but not limited to: such as the element of sulphur, phosphorus and silicon; Nonmetal as nitrogen, fluorine and oxygen; Their combination; Deng.
[0010] the first step of preparation alcoxylates is to make Epicholorohydrin and the excessive alcohol reaction of stoichiometry.Need add Epicholorohydrin can keep the excessive any-mode of required stoichiometry like this.For example, on extensive or technical scale, can add Epicholorohydrin continuously to alcohol.On the contrary, on (for example, laboratory scale) on a small scale, can adopt " progressively " mode more expediently.This can be included in and add a certain amount of Epicholorohydrin at least in 3 steps each, and in some non-limiting embodiments, adds a certain amount of Epicholorohydrin in each at least 5 steps.Time between the step can change, and condition is to keep the excessive of required alcohol in entire reaction.In some non-limiting embodiments, this time can be about 30 minutes to about 90 minutes; In other non-limiting embodiments, it can be about 45 minutes to about 75 minutes; And in other non-limiting embodiments, it can be about 60 minutes.Progressively add the heat release that may help to control such small-scale reaction especially.
[0011] excessive to be defined as the institute that is illustrated in the entire reaction free with stoichiometry in this article, and alcohol is present in reaction with 3 times amount based on the stoichiometric amount of Epicholorohydrin at least, that is, alcohol: the Epicholorohydrin mol ratio was at least about 3: 1.Yet finding usefully increases the relative quantity or the ratio of interpolation Epicholorohydrin then in certain embodiments with very big pure excessive beginning in 10: 1 to about 20: 1 according to appointment towards the terminal point of reaction, and until alcohol: the Epicholorohydrin ratio is about 3: 1.In other non-limiting embodiments, can carry out the reaction of success by the following method: no matter progressively or continuously add Epicholorohydrin, increase the amount or the ratio that add Epicholorohydrin towards the terminal point that reacts then and make pure: the ratio of Epicholorohydrin was reduced to about 3: 1 to about 16: 1 ratio in about 15: 1 in maintenance in most of process of reaction.In the process that Epicholorohydrin is mixed in the reaction, adopt such control scheme except helping to control heat release, can also help to reduce the amount of so-called heavies (heavies).These heavies that produced by the further reaction of alkoxyl group-ether are the impurity in the final product, and its boiling point is higher than the boiling point of required alkoxyl group-ether.
[0012] this reaction also comprises the existence of alkaline environment and phase-transfer catalyst aptly.Alkaline environment can obtain by adding metal hydroxides, and described metal hydroxides comprises 1A family metal, for example, and sodium hydroxide or potassium hydroxide.In some non-limiting embodiments, can before adding Epicholorohydrin, metal hydroxides and alcohol be merged, and under some other situation, more not in the embodiment preferred, metal hydroxides and alcohol side by side can be merged with Epicholorohydrin.
[0013] total molar ratio of alcohol, metal hydroxides and Epicholorohydrin can change in following scope and/or in these scopes: in some non-limiting embodiments, from the extremely final about 1/0.7/0.2-1/0.7/0.33 of mol ratio of about 1/0.7/0.06, and in a specific embodiments, to about 1/0.7/0.3.In other non-limiting embodiments, in most of duration of the reaction, the ratio of alcohol/metal hydroxides/Epicholorohydrin can be at about 1/0.7/0.01 to the scope of about 1/0.7/0.8 after progressively carrying out just having added Epicholorohydrin each time under the situation or in continuous production, preferred about 1/0.7/0.02 is to about 1/0.7/0.1, and 1/0.7/0.05 about 1/0.7/0.07 extremely more preferably from about.In some non-limiting embodiments, this ratio can rise to the scope of about 1/0.7/0.2 to 1/0.7/0.33, preferably about 1/0.7/0.33 towards the terminal point of reaction.
[0014] phase-transfer catalyst that is used for the reaction between alcohol and the Epicholorohydrin can be selected from those skilled in the art's known those phase-transfer catalysts usually.For example, those that can select comprise and contain the anionic salt that is selected from the group of being made up of halogen root, methylsulfate and bisulfate ion, such as alkyl dimethyl benzyl ammonium salt, tetraalkylammonium salt, N, N, N-trialkyl-3-alkoxyl group-2-hydroxypropyl ammonium salt and alkyl trimethyl ammonium salt.Other example comprises: trialkylamine, N, N-dialkyl amido-3-alkoxyl group-2-propyl alcohol, Tetrabutylammonium bromide, the hydrogen sulfate TBuA, cetyltrimethylammonium chloride, dodecyl dimethyl benzyl ammonium chloride, N, N-dimethylamino-3-hexyloxy-2-propyl alcohol, N, N-dimethyl-amino-3-octyloxy-2-propyl alcohol, N, N-dimethylamino-3-dodecyloxy-2-propyl alcohol, N, N-dimethylamino-3-octadecane oxygen base-2-propyl alcohol, N, N-dimethylamino-3-(1 ' H, 1 ' H, 2 ' H, 2 ' H-perfluor) hexyloxy-2-propyl alcohol, N, N-dimethyl-amino-3-(1 ' H, 1 ' H, 2 ' H, 2 ' H-perfluor)-octyloxy-2-propyl alcohol, N, N-two (2-hydroxyethyl)-amino-3-hexyloxy-2-propyl alcohol, N, N-two (2-hydroxyethyl) amino-3-octyloxy-2-propyl alcohol, N, N-two (2-hydroxyethyl) amino-3-dodecyloxy-2-propyl alcohol, N, N-two (2-hydroxyethyl) amino-3-octadecane oxygen base-2-propyl alcohol, N, N-two (2-hydroxyethyl)-amino-3-1 ' H, 1 ' H, 2 ' H, 2 ' H-perfluor) hexyloxy-2-propyl alcohol, methylsulfuric acid N, N-two (2-hydroxypropyl) ammonium, methylsulfuric acid N, N, N-trimethylammonium-3-octyloxy-2-hydroxypropyl ammonium, methylsulfuric acid N, N, N-trimethylammonium-3-dodecyloxy-2-hydroxyl-propyl ammonium, chlorination N, N, N-trimethylammonium-3-octyloxy-2-hydroxypropyl-ammonium, bromination N, N, N-trimethylammonium-3-octyloxy-2-hydroxypropyl ammonium, methylsulfuric acid N, N-two (2-hydroxyethyl)-N-methyl-3-hexyloxy-2-hydroxypropyl ammonium, methylsulfuric acid N, N-two (2-hydroxyl-ethyl)-N-methyl-3-octyloxy-2-hydroxypropyl ammonium, methylsulfuric acid N, N-two (2-hydroxyethyl)-N-methyl-3-dodecyloxy-2-hydroxypropyl ammonium, methylsulfuric acid N, N-two (2-hydroxyethyl)-N-methyl-3-octadecane oxygen base-2-hydroxypropyl ammonium, methylsulfuric acid N, N-two (2-hydroxyethyl)-N-methyl-3-(1 ' H, 1 ' H, 2 ' H, 2 ' H-perfluor)-hexyloxy-2-hydroxyl-propyl ammonium, methylsulfuric acid N, N-two (2-hydroxyethyl)-N-methyl-3-(1 ' H, 1 ' H, 2 ' H, 2 ' H-perfluor)-octyloxy-2-hydroxypropyl ammonium, sad and N, the esterification compound of N-dimethyl-3-octyloxy (oxtyloxy)-2-propyl alcohol, palmitic acid and N, the esterification compound of N-dimethyl-3-octyloxy-2-propyl alcohol, etc.Can alternatively select above-mentioned in any combination.
[0015] Epicholorohydrin carries out under the pressure of about 10 ℃ of promptly about 760-7600 holders to about 10atm to about 100 ℃ temperature and about 1 normal atmosphere (atm) aptly with the reaction of alcohol.Each when adding Epicholorohydrin and what suit in each process of adding Epicholorohydrin is that suitable mixed reactant is with the maximization that contacts with them.This can be by any means well known by persons skilled in the art or method for example, and turbomixer, oar blade type mixing tank, recirculation mixer wait and finish.
[0016] Fan Ying result forms reaction product.In some non-limiting embodiments, this reaction product can mainly be to have the good optionally dialkyl group-ether of selected alcohol in 1-position and 3-position.In other non-limiting embodiments, straight or branched 1,3-dialkyl group-ether can be at least about 50%; In other non-limiting embodiments, 1,3-dialkyl group-ether can be at least about 65%; And in other non-limiting embodiments, 1,3-dialkyl group-ether can be at least about 75%; All content promptly, does not comprise unreacted alcohol based on the weight of reaction product.
[0017] in second step, the reaction product and the oxirane that obtain are as mentioned above reacted to form 1,3-dialkyl group-ether alcoxylates.In some non-limiting embodiments, suitable oxirane is any oxirane that contains 2 to 12 carbon atoms.These comprise, for example, and oxyethane, propylene oxide, butylene oxide ring etc.In certain embodiments, can select oxyethane.In other non-limiting embodiments, can select propylene oxide, and in other non-limiting embodiments, can select the mixture of oxyethane and propylene oxide.Under the situation of the mixture that uses oxirane, product is a multipolymer.
[0018] form 1, this second step of 3-dialkyl group-ether alcoxylates carries out in the presence of at least a ionic catalyst aptly.In a suitable especially embodiment, use at least two kinds of ionic catalysts successively, wherein in the process of adding initial several moles oxirane, use cationic catalyst, in the process of adding required residual epoxide alkane, use anionic catalyst then.Alternatively, can use the ionic catalyst (that is positively charged ion or anionic) of single ionic catalyst or single type in the alkoxy process in the whole second time.
[0019] selectable cationic catalyst can comprise an acidic catalyst, i.e. cationic polymerisation catalyst is such as being called those of Knut Fridell-Kerafyrm thatch type catalysts.Such cationic catalyst can comprise, for example, and the fluorochemical of boron, aluminium, iron, tin and titanium and muriate, and the complex compound of these halogenide and ethyl ether.In one embodiment, can select boron trifluoride.In another embodiment, can select trifluoromethanesulfonic acid.In other embodiment, can select sulfuric acid or phosphoric acid.Can also use above-mentioned in any combination.
[0020] selectable anionic catalyst can comprise basic catalyst, i.e. anionic polymerization catalyst is such as 1A family metal hydroxides, for example potassium hydroxide.Can also select for example alkali metal alcoholates of initial alcohol, or in the fs of present method process, generate 1, the corresponding alkoxide of 3-dialkoxy-2-propyl alcohol.Such catalyzer can react in-situ preparing by neutralized reaction product and basic metal, alkalimetal oxide or the oxyhydroxide that makes first step of reaction, or can obtain with the form of pure composition.Can also select the combination of anionic catalyst.
[0021] straight or branched 1,3-dialkyl group-ether, and promptly 1, the ratio (mol ratio) of 3-dialkoxy-2-propyl alcohol and oxirane can be at about 1: 2 to about 1: 20 scope.In some non-limiting embodiments, this ratio can be about 1: 3 to about 1: 15, and it can be at about 1: 5 to about 1: 12 scope in other non-limiting embodiments.
[0022] final straight or branched, the oxirane expansion 1,3-dialkyl group-ether alcoxylates can be used for preparation and composition with any aequum.Yet, it be commonly known to those skilled in the art that tensio-active agent in many application level can about 0.05 to about 50 weight %, be more typically about 0.1 to the scope of about 30 weight %, and be about 0.5 to about 20 weight % in some purposes.Under the situation of needs, those skilled in the art can determine usage quantity by the general knowledge of Application Areas and the combination of routine test.
[0023] composition of the present invention comprises various by its preparation of making and product.These include but not limited to: urethane, Resins, epoxy, thermoplastics, lacquer, coating, metal product, the product for agriculture that comprises weedicide and sterilant, oil field product, paper pulp and paper product, fabric, water-treated prod, flooring product, ink, tinting material, medicine, cleaning product, personal care product, lubricant and these combination.In these and other preparation and product, alcoxylates can provide such as following character: surfactivity, soil release characteristics, wetting, rewetting, minimizing foam, stabilized latex, drug delivery capacity, emulsification, improve rinsing, plasticising, reaction dilution, rheology modified, improve suspension, false plasticising, thickening, sealing ability (capping capability), curing, impact modified, lubricated, emulsification and microemulsified, their combination etc.
[0024] example of these application comprises the following effectiveness of alcoxylates: generally as tensio-active agent; As the reaction diluent in curtain coating, encapsulation, floor, embedding (potting), tackiness agent, layered product, reinforced plastics and the long filament winding; The electrician uses as the coating of encapsulation magnetic coil and high tension coil as being used for; As wetting agent; As rinse aid; As froth breaking/low infusion; As spray cleaner; As the drug conveying agent; As weedicide and sterilant emulsifying agent; As metal detergent; As lacquer and coating suspension aids and emulsifying agent; Be used for the mixing toughener in the microcosmic multiphase mixture of organic compound of the polarity of agricultural spreading agent and plant growth agent and non-polar support fluid as preparation; As the latex stablizer; As paper pulp and paper product micro-emulsifier; Deng.In a non-limiting embodiments, adopt the composition of alcoxylates to comprise to be used for organic synthesis, formation, polymerization and biology inorganic and organic filler have machining and synthetic, and the microemulsion of their combination.In another non-limiting embodiments, the alcoxylates of Miao Shuing can be used for diluting the viscosity higher Resins, epoxy based on for example bisphenol-A, bisphenol-f and novolak herein, and other thermoplasticity and thermosetting polymer such as urethane and acrylic acid or the like.They can also be applied in liquid system such as ink, emulsion, lacquer and pigment suspension rheology modified, and wherein they can also be used to give pseudo-plasticity or thixotropic flow.In these and other purposes, alcoxylates can provide good performance and excellent performance is provided in some cases, and lower cost.
[0025] it be commonly known to those skilled in the art that in such application tensio-active agent and be used for the level of the preparation of such application can be about 0.05 to about 50 weight %, more frequent for about 0.1 to the scope of about 30 weight % in some purposes for about 0.5 to about 20 weight %.Under the situation of needs, those skilled in the art can determine usage quantity by the general knowledge of Application Areas and the combination of routine test.
[0026] abovely describes that to be intended to be generalized, comprise that institute of the present invention might embodiment and be not intended to.Similarly, following examples only provide for explanation, limit by any way or restriction the present invention and be not intended to.In addition, those skilled in the art will be clear fully, consider that from specification sheets of the present invention disclosed herein and/or enforcement other embodiment within the scope of the claims is tangible.Other embodiment like this can comprise selects concrete alcohol, catalyzer and such combination of compounds, the ratio of such compound, mixing and reaction conditions, container and scheme, performance and selectivity, use in addition not at dialkyl group-ether alcoxylates this specifically described straight or branched, the oxirane expansion, etc.; And those skilled in the art will recognize that these can change in the scope of appended claim.
Embodiment
Embodiment 1
A. side chain 1, the preparation of 3-dialkoxy-2-propyl alcohol
[0027] under not strict situation of removing air or moisture, adds Tetrabutylammonium bromide, the finely disintegrated sodium hydroxide of about 66.4g and the 2-methyl isophthalic acid-enanthol of about 305.7g of about 24.4g in 1 litre bottle in the film cover.Shake the bottle so that the Tetrabutylammonium bromide dissolving.The 1-chloro-2 that adds about 13.1g then, the 3-propylene oxide, and shake the bottle with mixing suspension.
[0028] after one hour, add the 1-chloro-2 of about 13.1g once more, the 3-propylene oxide, and shake the bottle with mixing suspension.Carry out at interval 3 times 1-chloro-2 in addition with 1 hour, the adding of 3-propylene oxide, such adding 5 times altogether amount to the 1-chloro-2 of 65.4g, 3-propylene oxide.Until all 1-chloro-2, the 3-propylene oxide is consumed by the vapor-phase chromatography monitoring reaction.
[0029] analytical reaction product then, it contains some 1,3-two-(2-methyl oxygen in heptan base)-2-propyl alcohol.
[0030] reaction that will describe herein repeats 16 times.Then the batch of material (bacthes) that merges is filtered removing salt and unreacted sodium hydroxide by thick agglomerating glass funnel, and use deionized water wash filtrate.On rotatory evaporator with the heating bath that is set in 90 ℃, carry out stripping by reducing pressure until the resulting pressure that reaches about 0.5mm with the speed that prevents bumping, the lighting end that is mainly 2-methyl isophthalic acid-enanthol is removed.Have through steam stripped material more a high proportion of 1,3-two-(2-methyl oxygen in heptan base)-2-propyl alcohol.
B.1, the separation of 3-two-(2-methyl oxygen in heptan base)-2-propyl alcohol
[0031] distillation is through steam stripped material in the batch distillation device, and described batch distillation device is by forming with 2 liters of jars, magnetic agitation, thermocouple sheath and the monoblock type still head/condenser of heating jacket heating.Distillation is carried out to expiring vacuum pump pressure (0.2 to 0.5mm) and increasing sleeving temperature lentamente by reducing pressure.The cut of obtaining in the temperature that is lower than 155 ℃ overhead distillate temperature contains lighting end, such as 2-methyl isophthalic acid-enanthol and 1-(2-methyl oxygen in heptan base)-3-chloro-2-propyl alcohol.1,3-two-(2-methyl oxygen in heptan base)-2-propyl alcohol is when the overhead distillate product of overhead distillate temperature when about 138-160 ℃ and jar temperature are lower than 200 ℃.
C.1, the further separation of 3-two-(2-methyl oxygen in heptan base)-2-propyl alcohol
[0032] the initial distillation in above " B " part produces and comprises 1, the product of 3-two-(2-methyl oxygen in heptan base)-2-propyl alcohol and unsuitable pollutent 1-(2-methyl oxygen in heptan base)-3-chloro-2-propyl alcohol.In product of distillation, add highly basic, try hard to 1-(2-methyl oxygen in heptan base)-3-chloro-2-propyl alcohol is converted into 2-methylheptyl glycidyl ether, expect that it further reacts formation higher-boiling compound.To be handled through steam stripped material merging and with sodium hydride with remaining by the cut that 1-(2-methyl oxygen in heptan base)-3-chloro-2-propyl alcohol pollutes from the distillatory first time.The 60 weight % solution mineral oil of sodium hydride for receiving from the industrial production merchant, but with rough 1, this reinforced at first weight of the weight form record of 3-two-(2-methyl oxygen in heptan base)-2-propanol solution does not comprise mineral oil.This is at first reinforced roughly with mole such as chloro-hydrin(e) concentration and cause 1-(2-methyl oxygen in heptan base)-3-chloro-2-propyl alcohol concentration reduction according to estimates.Repeating the sodium hydride processing further reduces 1-(2-methyl oxygen in heptan base)-3-chloro-2-propyl alcohol concentration.Wash resulting hydride species with rare HCl, wash with saturated sodium carbonate subsequently.
[0032] then the rough material through washing is carried out the aforesaid batch distillation of another time.When the overhead distillate temperature is collected cut and merging during at about 138-160 ℃, thereby produce 1 of higher proportion, 3-two-(2-methyl oxygen in heptan base)-2-propyl alcohol.
D.
The preparation of side chain ether-alcoxylates (1, the oxyethyl group of 3-two-(2-methyl oxygen in heptan base)-2-propyl alcohol Change)
[0034] in independently reacting, uses potassium hydroxide (KOH), trifluoromethanesulfonic acid (CF
3SO
3H) or boron trifluoride (BF
3) as catalyzer, make 1 of 5 purifying, 3-two-(2-methyl oxygen in heptan base)-2-propyl alcohol sample separately with the reacting ethylene oxide of different molar weights.Molar weight is 2,6,9 and 12, and wherein two samples use 2 moles oxyethane preparation separately.
E.1, the application of ether-alcoxylates in latex formulations of 3-two-(2-methyl oxygen in heptan base)-2-propyl alcohol
[0035] with the water filling reactor of 81.3 weight parts, it has contained the seed latex of 1 weight %.Jar is heated to about 80 ℃ and purge with nitrogen.During about 4 hours, two kinds of independent mixtures are fed in the reactor.A kind of mixture is made up of the methacrylic acid of the vinylbenzene of about 50 parts by weight of acrylic butyl esters, about 47.5 weight parts, about 1.5 parts by weight of acrylic and about 1.0 weight parts.Another kind of mixture is made up of the sodium hydroxide in water (20 weight %) of the water of about 19.0 weight parts, the ethoxylation of about 1.5 weight parts-[1,3-two-(2-methyl oxygen in heptan base)-2-propyl alcohol], about 0.1 weight part and the Potassium Persulphate of about 0.7 weight part.After adding, reactor was kept about 30 minutes at about 80 ℃, make it be cooled to about 30 ℃ then.The latex products of Xing Chenging contains 44.4% solid of having an appointment thus, and monomer conversion is about 99% of a theoretical value.This latex products can be used as the component of lacquer formulations, binder formulation or paper coating preparation.
Embodiment 2
[0036] the wetting test of Draves (Draves Wetting Test) is carried out as the performance test of the wetting ability of the water phase surfactant mixture of an embodiment representing the present composition.This test relates to be determined to sink the required time when flock is in the water phase surfactant mixture that immerses various concentration.Data are illustrated in the required concentration of wetting flock in 20 seconds.At quick humidification and infiltration is that this information can be used for evaluation Example such as hard surface cleaner under the situation of key.The results are shown in the table 1, wherein be apparent that, very the tensio-active agent of lower concentration produces acceptable wetting ability, and shows further increase wetting ability than the long-chain alkylene oxide moiety.
Table 1
| As 1 of tensio-active agent, the ether-alcoxylates (mole number of the oxyethane of use) of the oxirane of 3-two-(2-methyl oxygen in heptan base)-2-propyl alcohol expansion | 20 seconds wetting concentration (the weight % of tensio-active agent) |
| 9 | ?0.12 |
| 12 | ?0.06 |
Claims (20)
1. composition, its comprise straight or branched oxirane expansion 1,3-dialkoxy-2-propyl alcohol alcoxylates.
2. the described composition of claim 1, wherein said alcoxylates contains the alkoxyl group part of straight chain.
3. the described composition of claim 1, wherein said alcoxylates contains the alkoxyl group part of side chain.
4. the described composition of claim 1, wherein said alcoxylates comprises 2 to 12 oxirane repeating units.
5. the described composition of claim 1, wherein said alcoxylates contains the alkoxyl group part of 3 to 28 carbon atoms.
6. the described composition of claim 5, it also comprises at least a heteroatoms that is selected from the group of being made up of IVA, VA, VIA and VIIA family element and their combination.
7. the described composition of claim 1, wherein said alcoxylates provides the character that is selected from the group of being made up of and the following to described composition: surfactivity, soil release characteristics, wetting, rewetting, minimizing foam, stabilized latex, drug delivery capacity, emulsification and microemulsified, improve rinsing, plasticising, reaction dilution, rheology modified, improve suspension, false plasticising, thickening, sealing ability, curing, impact modified, lubricated and their combination.
9. the described composition of claim 1, wherein said composition is the preparation that is selected from the group of being made up of and the following: polyurethane formulation, epoxy resin formulation, lacquer formulations, coating formulation, the metal treatment preparation, Agrotechnical formulation, the oil field preparation, paper pulp and paper treatment agent, the fabric preparation, the water treatment preparation, the floor preparation, ink formulations, colorant preparations, medicine preparation, cleaning formulation, the farm crop preparation, lubricant formulations, personal care product's preparation, latex formulations, the letex polymerization preparation, the suspension polymerization preparation, the emulsification preparation, the suspension treatment agent, dispersion treatment preparation and their combination.
10. the described method of claim 1, wherein said composition is the product that is selected from the group of being made up of and the following: urethane, Resins, epoxy, thermoplastics, lacquer, coating, metal product, product for agriculture, oil field product, paper pulp or paper product, fabric, water-treated prod, floor, ink, tinting material, medicine, cleaning product, personal care product, lubricant and their combination.
11. one kind prepares method for compositions, described method comprise with straight or branched, oxirane expansion 1,3-dialkoxy-2-propyl alcohol alcoxylates merges in the composition.
12. the described method of claim 11, wherein said alcoxylates contain the alkoxyl group part of straight chain.
13. the described method of claim 11, wherein said alcoxylates contain the alkoxyl group part of side chain.
14. the described method of claim 11, wherein said alcoxylates comprise 2 to 12 oxirane repeating units.
15. the described method of claim 11, wherein said alcoxylates contain the alkoxyl group part of 3 to 28 carbon atoms.
16. the described method of claim 15, wherein said alkoxyl group partly comprise at least a heteroatoms that is selected from the group of being made up of IVA, VA, VIA and VIIA family element and their combination.
17. the described method of claim 11 is wherein used described alcoxylates with about 0.05 to about 50 weight % amount.
18. the described method of claim 17 is wherein used described alcoxylates with about 0.1 to about 30 weight % amount.
19. the described method of claim 18 is wherein used described alcoxylates with about 0.5 to about 20 weight % amount.
20. the described method of claim 11, wherein said composition are the preparations that is selected from the group of being made up of and the following: polyurethane formulation, epoxy resin formulation, lacquer formulations, coating formulation, the metal treatment preparation, Agrotechnical formulation, the oil field preparation, paper pulp and paper treatment agent, the fabric preparation, the water treatment preparation, the floor preparation, ink formulations, colorant preparations, medicine preparation, cleaning formulation, the farm crop preparation, lubricant formulations, personal care product's preparation, latex formulations, the letex polymerization preparation, the suspension polymerization preparation, the emulsification preparation, the suspension treatment agent, dispersion treatment preparation and their combination.
21. the described method of claim 11, wherein said composition are the products that is selected from the group of being made up of and the following: urethane, Resins, epoxy, thermoplastics, lacquer, coating, metal product, product for agriculture, oil field product, paper pulp or paper product, fabric, water-treated prod, floor, ink, tinting material, medicine, cleaning product, personal care product, lubricant and their combination.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92663107P | 2007-04-27 | 2007-04-27 | |
| US60/926,631 | 2007-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101668728A true CN101668728A (en) | 2010-03-10 |
Family
ID=39591772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200880013819A Pending CN101668728A (en) | 2007-04-27 | 2008-04-24 | Novel alkoxylate-containing compositions |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP2152653A1 (en) |
| JP (1) | JP2010526778A (en) |
| CN (1) | CN101668728A (en) |
| BR (1) | BRPI0809790A2 (en) |
| CA (1) | CA2685319A1 (en) |
| MX (1) | MX2009011606A (en) |
| RU (1) | RU2009143873A (en) |
| WO (1) | WO2008134389A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104093690A (en) * | 2012-02-08 | 2014-10-08 | 株式会社大赛璐 | Polyglycerin dialkyl or alkenyl ether, and cosmetic composition containing same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2823476A1 (en) | 2012-09-17 | 2014-03-17 | Dow Global Technologies Llc | Surfactant compositions and use for aqueous compositions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2932616A (en) * | 1957-02-19 | 1960-04-12 | Monsanto Chemicals | Detergent compositions |
| FR2102536A5 (en) * | 1970-08-07 | 1972-04-07 | Ugine Kuhlmann | Glycerol derivs surfactants - by reacting a glyceryl di ether with ethylene oxide |
| JPS5993022A (en) * | 1982-11-16 | 1984-05-29 | Kao Corp | Polyol ether compound, its preparation and cosmetic containing the same |
| JPS60224638A (en) * | 1984-04-23 | 1985-11-09 | Kao Corp | Percutaneous absorption promoter and external drug containing same |
| JPH07292383A (en) * | 1994-04-22 | 1995-11-07 | Nok Corp | Production of release agent composition |
| JPH0859545A (en) * | 1994-08-24 | 1996-03-05 | Kao Corp | Carboxyethyl ether derivative and detergent composition containing the same |
-
2008
- 2008-04-24 CA CA002685319A patent/CA2685319A1/en not_active Abandoned
- 2008-04-24 EP EP08746730A patent/EP2152653A1/en not_active Withdrawn
- 2008-04-24 CN CN200880013819A patent/CN101668728A/en active Pending
- 2008-04-24 JP JP2010506485A patent/JP2010526778A/en not_active Withdrawn
- 2008-04-24 WO PCT/US2008/061364 patent/WO2008134389A1/en active Application Filing
- 2008-04-24 MX MX2009011606A patent/MX2009011606A/en not_active Application Discontinuation
- 2008-04-24 RU RU2009143873/04A patent/RU2009143873A/en not_active Application Discontinuation
- 2008-04-24 BR BRPI0809790-9A2A patent/BRPI0809790A2/en not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104093690A (en) * | 2012-02-08 | 2014-10-08 | 株式会社大赛璐 | Polyglycerin dialkyl or alkenyl ether, and cosmetic composition containing same |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008134389A1 (en) | 2008-11-06 |
| RU2009143873A (en) | 2011-06-10 |
| JP2010526778A (en) | 2010-08-05 |
| CA2685319A1 (en) | 2008-11-06 |
| EP2152653A1 (en) | 2010-02-17 |
| MX2009011606A (en) | 2009-12-04 |
| BRPI0809790A2 (en) | 2014-10-07 |
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