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EP1542955B1 - Alcoxylats presentant une faible teneur en alcool residuel - Google Patents

Alcoxylats presentant une faible teneur en alcool residuel Download PDF

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Publication number
EP1542955B1
EP1542955B1 EP03725099A EP03725099A EP1542955B1 EP 1542955 B1 EP1542955 B1 EP 1542955B1 EP 03725099 A EP03725099 A EP 03725099A EP 03725099 A EP03725099 A EP 03725099A EP 1542955 B1 EP1542955 B1 EP 1542955B1
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EP
European Patent Office
Prior art keywords
compositions
composition
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content
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Revoked
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EP03725099A
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German (de)
English (en)
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EP1542955A1 (fr
Inventor
Christian Wulff
Kai-Uwe Baldenius
Martin Scholtissek
Michael Stösser
Norbert Wagner
Edward Bohres
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BASF SE
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BASF SE
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups

Definitions

  • the present invention relates to compositions containing at least one alkoxylate of the general formula RO (A) n (B) m H, to processes for preparing such compositions, in particular in the presence of double metal cyanide compounds as catalyst, and to their use as emulsifier, foam regulator or wetting agent for hard surfaces. Moreover, the present invention also relates to the use of such compositions in detergents and surfactant formulations.
  • Alkoxylates of aliphatic alcohols are widely used as surfactants, emulsifiers or foam suppressants.
  • the wetting and emulsifying properties depend strongly on the type of alcohol and the type and amount of alkoxide adducts.
  • WO 94/11331 relates to the use of alkoxylates of 2-propylheptanol in detergent compositions for degreasing hard surfaces.
  • the alkoxylates have 2 to 16 alkylene oxide groups.
  • the major part of the alkylene oxide groups is in the form of ethylene oxide.
  • ethoxylated alcohols are used. It is further described that the alcohols can be reacted first with ethylene oxide and then with propylene oxide.
  • such alkoxylates are not examples or properties specified. It is stated that the described alkoxylates show a good detergent and wetting action, combined with a low foaming. In addition, it is stated that the alkoxylates have a desired thickening effect in formulations.
  • WO 94/11330 relates to alkoxylates of 2-propylheptanol and their use.
  • the alkoxylates is 2-propylheptanol, first with 1 to 6 moles of propylene oxide and then reacted with 1 to 10 moles of ethylene oxide before.
  • a 2-propylheptanol reacted first with 4 mol of propylene oxide and then with 6 mol of ethylene oxide is used.
  • the alkylene oxide adducts show an improved foam behavior to detergent effect.
  • the alkoxylates show a good wetting behavior. They are used in detergent compositions for cleaning textile materials.
  • US 2,508,036 relates to the use of 2-n-propylheptanolethoxylates containing from 5 to 15 moles of ethylene oxide as wetting agents in aqueous solutions. It is described that the products can be used as surfactants in detergents.
  • the DE-A-102 18 754 as well as the DE-A-102 18 753 relate to the use of C 10 -alkanolalkoxylate mixtures, in particular alkanolethoxylate mixtures, such C 10 -alkanol alkoxylate mixtures and processes for their preparation.
  • the DE-A-102 18 752 also describes alkoxylate mixtures and detergents containing them, as well as processes for the preparation of the alkoxylate mixtures and the use of the detergent for washing or cleaning textiles.
  • WO 02/50006 relates to branched primary alcohol-containing compositions and derivatives thereof.
  • a product derived from a branched primary C 9-24 alcohol initially reacted with one mole of propylene oxide and then ethylene oxide is described.
  • the alcohol can not be a primary alcohol because the R 2 group is a hydrocarbyl group.
  • the avoidance of larger amounts of residual alcohol present in the product is particularly advantageous for odor reasons.
  • the alcohol mixtures used according to the invention generally have an inherent odor which can be largely suppressed by complete alkoxylation. Alkoxylates obtained by conventional methods often have an inherent odor which is responsible for many applications are annoying. Furthermore, improved hard surface wetting, improved emulsification behavior, and lower CMC (Critical Micell Concentration) are desirable.
  • n and m denote an average value which is the average over all molecules. Therefore, n and m can also differ from integer values.
  • Propyleneoxy is in the context of the present invention for -CH 2 -CH (CH 3 ) -O- or - CH (CH 3 ) -CH 2 -O-.
  • Ethylenoxy stands for -CH 2 -CH 2 -O-.
  • propylene oxide is attached in a ring-opening manner to the radical RO.
  • n indicates the number of propylene oxide groups and is a whole or fractional number with 0 ⁇ n ⁇ 1.
  • Ethylene oxide or a mixture of ethylene oxide and propylene oxide is bound to the propylene oxide group.
  • M stands for the number of ethylene oxide or ethylene oxide and propylene oxide groups and is a whole or fractional number with 0 ⁇ m ⁇ 20, preferably 1 ⁇ m ⁇ 18, in particular 2 ⁇ m ⁇ 14, for example 2.5 ⁇ m ⁇ 14 or 3 ⁇ m ⁇ 8.
  • the present invention relates to compositions wherein m is an integer or fractional number from 2 to 14.
  • compositions according to the invention have a low residual alcohol content. It is surprising that the residual alcohol content in the compositions according to the invention which have a defined amount of propylene oxide and subsequently ethylene oxide or ethylene oxide and propylene oxide is lower than would theoretically be expected. From residual alcohol contents of products which contain only propylene oxide or only ethylene oxide, an expected value can be determined which is higher than the residual alcohol content actually determined for the copolymers according to the invention.
  • the alkoxylates contained in the compositions of the invention require to lower the residual alcohol content only a directly bound to the alcohol propylene oxide (PO) block of very short length. This is particularly advantageous because the biodegradability of the product decreases as the PO block lengthens. Such alkoxylates thus allow maximum degrees of freedom in the choice of the length of the PO block, the length down through the rising Residual alcohol content and is limited upwards by the deterioration of biodegradability. This is particularly advantageous if only a short ethylene oxide block follows the PO block.
  • PO alcohol propylene oxide
  • alkoxylates contained in the compositions of the invention can then be initially present in the alcohol radical propyleneoxy units and then ethyleneoxy units. If n and m have a value of more than 1, the corresponding alkoxy radicals are preferably present in block form.
  • a distribution of the degree of alkoxylation is generally obtained, which can be adjusted to some extent by using different alkoxylation catalysts.
  • Groups A and B the property spectrum of the compositions of the invention can be adjusted according to practical requirements. Particularly preferred is first reacted with propylene oxide and then with ethylene oxide.
  • the present invention relates to compositions in which B is ethyleneoxy.
  • the alkyl radical R is in the context of the present invention C 5 H 11 CH (C 3 H 7 ) CH 2 -, except isomer mixtures of an alkyl group of the general empirical formula C 5 H 11 CH (C 3 H 7 ) CH 2 - from 70 to 99% by weight a radical R1 in which C 5 H 11 has the meaning nC 5 H 11 and 1 to 30% by weight of a radical R2 in which C 5 H 11 has the meaning C 2 H 5 CH (CH 3 ) CH 2 and / or CH 3 CH (CH 3 ) CH 2 CH 2 .
  • the alcohols used as starter compound may also be mixtures of different isomers.
  • compositions according to the invention can be used as catalyst.
  • the compositions of the invention thus obtained can have a residual metal content of greater than 0 and less than 50 ppm zinc (ie mg metal per kg product), in particular greater than 0 and less than 25 ppm zinc or preferably greater than 0 and less than 15 ppm zinc and greater as 0 and less than 25 ppm cobalt, in particular greater than 0 and less than 15 ppm cobalt or preferably greater than 0 and less than 7 ppm cobalt.
  • the present invention relates to compositions whose content of zinc is greater than 0 and less than or equal to 15 ppm or whose content of cobalt is greater than 0 and less than or equal to 7 ppm or whose content of zinc is greater than 0 and smaller or equal to 15 ppm and their content of cobalt is greater than 0 and less than or equal to 7 ppm.
  • the present invention also relates to a process for preparing the compositions by reacting at least one alcohol C 5 H 11 CH (C 3 H 7 ) CH 2 -OH with propylene oxide and ethylene oxide under alkoxylation conditions.
  • the content of residual alcohol in the alkoxylates can be reduced since propylene oxide is added more uniformly to the alcohol component.
  • ethylene oxide preferably reacts with ethoxylates, such that upon initial use of ethylene oxide to react with the alkanols, both a broad homolog distribution and a high residual alcohol content result.
  • the avoidance of larger amounts of residual alcohol present in the product is particularly advantageous for odor reasons.
  • the addition reaction is carried out at temperatures of about 90 to 240 ° C, preferably from 110 to 190 ° C, in a closed vessel.
  • the alkylene oxide or the mixture of different alkylene oxides is fed to the mixture of alkanol mixture according to the invention and catalyst under the vapor pressure of the alkylene oxide mixture prevailing at the selected reaction temperature or at a higher pressure.
  • the alkylene oxide may be diluted with an inert gas (for example noble gases, nitrogen, CO 2) up to 99.9%.
  • Suitable alkoxylation conditions are described above and in Nikolaus Schonfeldt, Grenz inhabitassitule ⁇ thylenoxid adducts,ticianliche Verlagsgesellschaft mbH Stuttgart 1984 described.
  • the alkoxylation is carried out in the presence of basic catalysts such as KOH in substance.
  • the alkoxylation can also be carried out with the concomitant use of a solvent.
  • the alcohols are first reacted with a suitable amount of propylene oxide and then with a suitable amount of ethylene oxide.
  • a polymerization of the alkylene oxide is set in motion, which inevitably leads to a statistical distribution of homologues whose mean value is given here with n and m.
  • the length of the polyether chains (n + m) varies randomly within the reaction product by an average, which essentially results from the addition amount and the stoichiometric values.
  • different molecular weight distributions are obtained. For example, products with a narrow molecular weight distribution often have good solubility.
  • the alkoxylation is catalyzed by strong bases, which are suitably added in the form of an alkali metal alcoholate, alkali metal hydroxide, alkaline earth metal oxide or alkaline earth metal hydroxide, usually in an amount of 0.01 to 1 wt .-% based on the amount of the alkanol R-OH , (comp. G. Gee et al., J. Chem. Soc. (1961), p. 1345 ; B. Wojtech, Makromol. Chem. 66, (1966), p. 180 ).
  • Acid catalysis of the addition reaction is also possible.
  • Lewis acids such as AlCl 3 or BF 3 dietherate, BF 3 , BF 3 x H 3 PO 4 , SbCl 4 x 2 H 2 O hydrotalcite (Cf. PH Plesch, The Chemistry of Cationic Polymerization, Pergamon Press, New York (1963 )).
  • DMC double metal cyanide
  • the present invention relates to a process carried out in the presence of a double metal cyanide compound as a catalyst. Therefore, in a preferred embodiment, the present invention relates to a method for Preparation of compositions wherein the alkoxylation is carried out in the presence of a double metal cyanide compound (DMC compound) as a catalyst.
  • DMC compound double metal cyanide compound
  • DMC compound As a DMC compound, it is possible in principle to use all suitable compounds known to the person skilled in the art.
  • the organic additives P are: polyethers, polyesters, polycarbonates, polyalkylene glycol sorbitan esters, polyalkylene glycol glycidyl ethers, polyacrylamide, poly (acrylamide-co-acrylic acid), polyacrylic acid, poly (acrylamide-co-maleic acid), polyacrylonitrile, polyalkyl acrylates, polyalkyl methacrylates, polyvinyl methyl ether, polyvinyl ethyl ether, Polyvinyl acetate, polyvinyl alcohol, poly-N-vinylpyrrolidone, poly (N-vinylpyrrolidone-co-acrylic acid), polyvinyl methyl ketone, poly (4-vinylphenol), poly (acrylic acid-co-styrene), oxazoline polymers, polyalkyleneimines, maleic and maleic anhydride copolymers, hydroxyethylcellulose, Polyacetates, ionic surfactants and surface-active compounds,
  • catalysts can be crystalline or amorphous. In the case where k is zero, crystalline double metal cyanide compounds are preferred. In the case where k is greater than zero, both crystalline, partially crystalline, and substantially amorphous catalysts are preferred.
  • a preferred embodiment is catalysts of the formula (I) in which k is greater than zero.
  • the preferred catalyst then contains at least one double metal cyanide compound, at least one organic ligand and at least one organic additive P.
  • k is zero, optionally e is also zero and X is exclusively a carboxylate, preferably formate, acetate and propionate.
  • Such catalysts are in the WO 99/16775 described.
  • crystalline double metal cyanide catalysts are preferred.
  • double metal cyanide catalysts as in WO 00/74845 described which are crystalline and platelike.
  • the preparation of the modified catalysts is carried out by combining a metal salt solution with a cyanometalate solution, which may optionally contain both an organic ligand L and an organic additive P. Subsequently, the organic ligand and optionally the organic additive are added.
  • an inactive double metal cyanide phase is first prepared and then converted by recrystallization in an active Doppelmetallcyanidphase, as in PCT / EP01 / 01893 described.
  • f, e and k are not equal to zero.
  • the catalysts can be prepared either with vigorous stirring (24,000 rpm with Turrax) or with stirring as in the US 5,158,922 described.
  • catalyst for the alkoxylation double metal cyanide compounds containing zinc, cobalt or iron or two of them is particularly suitable.
  • Berlin Blue is particularly suitable.
  • crystalline DMC compounds Preference is given to using crystalline DMC compounds.
  • a Zn-Co type crystalline DMC compound is used as the catalyst containing zinc acetate as the further metal salt component.
  • Such compounds crystallize in monoclinic structure and have a platelet-shaped habit.
  • Such compounds are used for example in the WO 00/74845 or the PCT / EP01 / 01893 described.
  • DMC compounds suitable as catalyst can be prepared in any manner known to those skilled in the art.
  • the DMC compounds can be prepared by direct precipitation, "incipient wetness” method, by preparing a precursor phase and subsequent recrystallization.
  • the DMC compounds can be used as a powder, paste or suspension or be shaped into a shaped body, introduced into moldings, foams or the like, or applied to shaped bodies, foams or the like.
  • the catalyst concentration used for the alkoxylation, based on the final amount skeleton is typically less than 2000 ppm (ie mg catalyst per kg product), preferably less than 1000 ppm, in particular less than 500 ppm, particularly preferably less than 100 ppm, for example less than 50 ppm or 35 ppm, more preferably less than 25 ppm.
  • compositions according to the invention show good wetting on hard surfaces.
  • the advantageous wetting behavior of the mixtures according to the invention can be determined, for example, by measurements of the contact angle on glass, polyethylene oxide or steel.
  • the present invention therefore also relates to the use of a composition according to the invention or a composition prepared by a process according to the invention as emulsifier, foam regulator and hard surface wetting agent, in particular the use in detergents, hard surface detergent formulations, humectants, cosmetic, pharmaceutical and crop protection formulations, Lacquers, coating compositions, adhesives, leather degreasing agents, formulations for the textile industry, fiber processing, metal processing, food industry, water treatment, paper industry, fermentation or mineral processing and in emulsion polymerizations.
  • compositions according to the invention are followed by better performance, in particular fast cleaning processes. This is surprising insofar as the chain extension of the starting alcohol usually reduces the dynamic and wetting properties. With the compositions according to the invention, it is thus possible to increase the wetting speed of aqueous formulations.
  • the compositions according to the invention can thus also be used as solubilizers which, in particular, do not negatively but positively influence the wetting power of wetting aids, even in dilute systems. They can be used to increase the solubility of wetting agents in aqueous formulations containing nonionic surfactants. They serve in particular to increase the wetting speed in aqueous wetting agents.
  • compositions according to the invention serve to reduce the interfacial tension, for example in aqueous surfactant formulations.
  • the reduced interfacial tension can be determined, for example, by the pendant drop method. This also results in a better effect of the compositions of the invention as an emulsifier or co-emulsifier.
  • the compositions of this invention may also be used to reduce interfacial tension at short times, usually less than one second, or to accelerate the adjustment of interfacial tension in aqueous surfactant formulations.
  • Such formulations usually contain ingredients such as surfactants, builders, fragrances and dyes, chelating agents, polymers and other ingredients.
  • Typical formulations are, for example, in WO 01/32820 described.
  • Other ingredients suitable for different applications are in EP-A-0 620 270 .
  • compositions of the invention can be used in all areas in which the action of surfactants is necessary.
  • the present invention therefore also relates to washing, cleaning, wetting, coating, adhesive, leather degreasing, moisturizing or textile treatment compositions or to cosmetic, pharmaceutical or crop protection formulations comprising a composition according to the invention or a composition prepared by a method according to the invention.
  • the compositions preferably contain 0.1 to 20 wt .-% of the compositions.
  • compositions of the invention are characterized in particular by a low residual alcohol content, so that they are advantageously suitable for a variety of applications.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Polyethers (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (8)

  1. Composition, contenant au moins un produit d'alcoxylation de formule générale 1 :

            RO(A)n(B)mH     (I)

    dans laquelle
    - R est un radical alkyle de formule générale C5H11CH(C3H7)CH2-,
    - A est le groupe oxypropylène,
    - B est le groupe oxyéthylène ou un mélange d'oxyéthylène et oxypropylène,
    - n est un nombre entier ou fractionnaire, avec 0 < n < 1,
    - m est un nombre entier ou fractionnaire, avec 0 < m < 20,
    étant entendu que pour R sont exclus les mélanges d'isomères d'un radical alkyle de formule brute générale C5H11CH(C3H7)CH2- composé de 70 à 99 % en poids d'un radical R1, dans lequel C5H11 a la signification de n-C5H11 et 1 à 30 % en poids d'un radical R2, dans lequel C5H11 a la signification de C2H5CH (CH3) CH2 et/ou CH3CH(CH3)CH2CH2.
  2. Composition selon la revendication 1, caractérisée en ce que B est le groupe oxyéthylène.
  3. Composition selon l'une des revendications 1 ou, caractérisée en ce que m est un nombre entier ou fractionnaire valant de 2 à 14.
  4. Composition selon l'une quelconque des revendications 1 à 3, caractérisée en ce que la teneur en zinc de la composition est supérieure à 0 et inférieure ou égale à 15 ppm ou la teneur en cobalt est supérieure à 0 et inférieure ou égale à 7 ppm ou la teneur en zinc est supérieure à 0 et inférieure ou égale à 15 ppm et la teneur en cobalt est supérieure à 0 et inférieure ou égale à 7 ppm.
  5. Procédé pour la préparation de compositions selon l'une quelconque des revendications 1 à 4, par mise en réaction d'au moins un alcool C5H11CH(C3H7)CH2-OH avec de l'oxyde de propylène et de l'oxyde d'éthylène dans des conditions d'alcoxylation, l'alcoylation s'effectuant en présence d'un composé de type cyanure bimétallique en tant que catalyseur.
  6. Utilisation de compositions selon l'une quelconque des revendications 1 à 4, comme émulsifiant, régulateur de mousse et en tant qu'agent mouillant pour surfaces dures.
  7. Utilisation selon la revendication 6, dans des produits de lavage, des compositions de tensioactifs pour le nettoyage de surfaces dures, des produits pour la rétention d'eau, des compositions cosmétiques, pharmaceutiques et phytosanitaires, des peintures, des produits de revêtement, des adhésifs, des dégraissants pour le cuir, des compositions pour l'industrie textile, la transformation de fibres, la transformation de métaux, l'industrie alimentaire, le traitement de
    l'eau, l'industrie du papier, la fermentation ou la transformation de minéraux et dans des polymérisations en émulsion.
  8. Produit de lavage, de nettoyage, agent mouillant, produit de revêtement, adhésif, produit pour le dégraissage du cuir, produit pour la rétention d'eau et le traitement de textiles ou composition cosmétique, pharmaceutique ou phytosanitaire, contenant des compositions selon l'une quelconque des revendications 1 à 4.
EP03725099A 2002-09-18 2003-04-25 Alcoxylats presentant une faible teneur en alcool residuel Revoked EP1542955B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10243365 2002-09-18
DE10243365A DE10243365A1 (de) 2002-09-18 2002-09-18 Alkoxylate mit niedrigem Restalkohol-Gehalt
PCT/EP2003/004330 WO2004033405A1 (fr) 2002-09-18 2003-04-25 Alcoxylats presentant une faible teneur en alcool residuel

Publications (2)

Publication Number Publication Date
EP1542955A1 EP1542955A1 (fr) 2005-06-22
EP1542955B1 true EP1542955B1 (fr) 2010-10-06

Family

ID=31969218

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03725099A Revoked EP1542955B1 (fr) 2002-09-18 2003-04-25 Alcoxylats presentant une faible teneur en alcool residuel

Country Status (12)

Country Link
US (1) US7332465B2 (fr)
EP (1) EP1542955B1 (fr)
JP (1) JP5134762B2 (fr)
CN (1) CN1296337C (fr)
AT (1) ATE483675T1 (fr)
AU (1) AU2003227678A1 (fr)
BR (1) BR0314399A (fr)
CA (1) CA2499351A1 (fr)
DE (2) DE10243365A1 (fr)
ES (1) ES2353745T3 (fr)
MX (1) MXPA05002906A (fr)
WO (1) WO2004033405A1 (fr)

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CN106176289A (zh) * 2009-09-15 2016-12-07 联合碳化化学品及塑料技术公司 用于个人护理组合物的聚硅氧烷替代物
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Also Published As

Publication number Publication date
EP1542955A1 (fr) 2005-06-22
JP2005539133A (ja) 2005-12-22
WO2004033405A1 (fr) 2004-04-22
US20050272626A1 (en) 2005-12-08
BR0314399A (pt) 2005-07-19
US7332465B2 (en) 2008-02-19
CN1296337C (zh) 2007-01-24
ATE483675T1 (de) 2010-10-15
AU2003227678A1 (en) 2004-05-04
MXPA05002906A (es) 2005-05-27
CN1688529A (zh) 2005-10-26
JP5134762B2 (ja) 2013-01-30
DE50313163D1 (de) 2010-11-18
ES2353745T3 (es) 2011-03-04
DE10243365A1 (de) 2004-04-01
CA2499351A1 (fr) 2004-04-22

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