DE10218754A1 - New and known 2-propyl-heptan-1-ol alkoxylates, used e.g. in cleaning, coating, adhesive, textile treatment, cosmetic, pharmaceutical or plant protection formulations, contain ethylene oxide and other alkylene oxide groups - Google Patents

Abstract

2-Propyl-heptan-1-ol alkoxylates (IA) with 3-14 ethylenoxy and 1.2-1.8 propylenoxy or pentenoxy or 1-1.8 butenoxy groups in the molecule are new. 2-Propyl-heptan-1-ol alkoxylates (IA) of formula (I), with specified numbers of alkoxylate groups, are new. A = propylenoxy, butenoxy or pentenoxy; n = 1.2-1.8 or, if A is butenoxy, 1-1.8; and m = 3-14. Independent claims are also included for the following: (1) use of a wider range of alkoxylates of formula (I; where n = 1-8; m = 2-20) as emulsifiers, foam regulators and wetting agents for hard surfaces; (2) preparation of alkoxylates (IA) by reacting the alkanol with propylene oxide and then with ethylene oxide under alkoxylation conditions, which can be carried out in the presence of a double metal cyanide compound as catalyst; (3) preparation of the alkanol by alkaline dimerization of valeraldehyde to an alpha,beta-unsaturated aldehyde, followed by hydrogenation; and (4) cleaning, wetting, coating, adhesive, leather degreasing, humectant, textile treatment or cosmetic, pharmaceutical or plant protection formulations containing (I).

Description

The present invention relates to the use of C ₁₀ alkanol alkoxylates, such C ₁₀ alkanol alkoxylates and processes for their preparation.

Alkoxylates of aliphatic alcohols are widely used as surfactants and Emulsifiers used. The wetting and emulsifying properties are strongly dependent 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 on. Preferably, the major part of the alkylene oxide Groups in the form of ethylene oxide. According to the examples become exclusive ethoxylated alcohols used. It is further described that the alcohols first with Ethylene oxide and then reacted with propylene oxide. For such However, alkoxylates are not given examples or properties. It is executed that the alkoxylates described have a good detergent and wetting action, associated with low foaming. In addition, it is stated that the alkoxylates have a desirable thickening effect in formulations.

WO 94/11330 relates to alkoxylates of 2-propylheptanol and their use. In the Alkoxylates is 2-propylheptanol, first with 1 to 6 moles of propylene oxide and then with 1 to 10 mol of ethylene oxide reacted before. According to the examples, a first with 4 mol Propylene oxide and then reacted with 6 moles of ethylene oxide 2-propylheptanol used. It is stated that the alkylene oxide adducts have an improved ratio of Show foam behavior to detergent effect. It is further stated that the alkoxylates show a good wetting behavior. They are used in detergent compositions for Cleaning of textile materials used.

The object of the present invention is to provide alkanol alkoxylates which are known as Emulsifier, foam regulator and as a wetting agent for hard surfaces are suitable. The Alkoxylates should in particular have a good emulsifying behavior and a low level of emulsification Contact angles on hard surfaces during application show. Furthermore, they should the Reduce interfacial tension in liquid systems. The alkoxylates should generally be advantageous property spectrum when used as emulsifier, foam regulator or as a wetting agent show. Furthermore, the products should have a favorable ecological Profile, d. H. not be aquatic: values EC 50 for algae, daphnia or fish greater than 10 mg / l; and easily degradable according to OECD 301 A-F. For this purpose, the Restalkoholgehalt be reduced compared to the ethoxylates. This should be for a variety of Applications as a disturbing odor caused by the residual alcohol content be avoided.

The object is achieved according to the invention by the use of alkoxylates of the general formula (I)

C ₅ H ₁₁ CH (C ₃ H ₇ ) CH ₂ O (A) _n (CH ₂ CH ₂ O) _m H (I)

with the meaning
A butenoxy, pentenoxy or preferably propyleneoxy,
n number in the range of 1 to 8,
m number in the range of 2 to 20,
as emulsifier, foam regulator and wetting agent for hard surfaces. It has been found according to the invention that the above alkoxylates of the general formula (I) exhibit outstanding emulsifier properties and can be used as non-foaming or low foaming wetting agents for hard surfaces. The alkoxylates exhibit low contact angles during hard surface wetting and allow the adjustment of low interfacial tensions in liquid systems.

Thus, the alkoxylates of general formula (I) are particularly advantageously used in Surfactant formulations for cleaning hard surfaces, in humectants, cosmetic, pharmaceutical and crop protection formulations, varnishes, Coating compositions, adhesives, leather fatliquors, formulations for metal processing, Food industry, water treatment, paper industry, fermentation, Mineral processing and in emulsion polymerizations. On the individual application areas is will be discussed in more detail below.

In the general formula (I), n is preferably a number in the range of 1 to 6, particularly preferably from 1 to 4, in particular from 1.3 to 2.3. According to a special preferred embodiment, n is a number in the range of 1.2 to 1.8, especially preferably 1.3 to 1.7, especially 1.4 to 1.6, especially about 1.5. m is preferably a number in the range of 3 to 14, more preferably 3 to 10.

In the alkoxylates according to the invention, the alcohol residue is then initially Propyleneoxy units and then ethyleneoxy units before. Have n and m a value of more than 1, the corresponding alkoxy radicals are in block form. n and m denote an average value which is the average for the alkoxylates results. Therefore, n and m can also differ from integer values. In the Alkoxylation of alkanols generally becomes a distribution of the degree of alkoxylation obtained to some extent by using different Alkoxylation catalysts can be adjusted. In the alkoxylates used in the invention was the alkanol is first reacted with propylene oxide and then with ethylene oxide.

The invention also relates to alkoxylates of the general formula (I)

C ₅ H ₁₁ CH (C ₃ H ₇ ) CH ₂ O (A) _n (CH ₂ CH ₂ O) _m H (I)

with the meaning
A butenoxy, pentenoxy or preferably propyleneoxy,
n is in the range from 1.2 to 1.8 when A is butoxy, from 1 to 1.8, preferably from 1.2 to 1.8,
m number in the range of 3 to 14.

In this case, n is preferably a number in the range from 1.3 to 1.7, in particular from 1.4 to 1.6. More preferably, n has a value of about 1.5. m is preferably a number in Range from 3 to 12, more preferably from 3 to 10, especially from 5 to 10.

In the general formula (I), the radical C ₅ H ₁₁ may be nC ₅ H ₁₁ , C ₂ H ₅ CH (CH ₃ ) CH ₂ or CH ₃ CH (CH ₃ ) CH ₂ CH ₂ . There may also be mixtures of two or more of these compounds. For example, the alkoxylates may be mixtures wherein
70 to 99 wt .-%, preferably 85 to 96 wt .-% alkoxylates A1 are present, in which C ₅ H _{11 is} nC ₅ H ₁₁ , and
1 to 30 wt .-%, preferably 4 to 15 wt .-% alkoxylates A2, in which C ₅ H _{11 is} C ₂ H ₅ CH (CH ₃ ) CH ₂ and / or CH ₃ CH (CH ₃ ) CH ₂ CH ₂ has.

The general formula (I) thus also includes such mixtures. In the general formula (I), the radical C ₃ H ₇ preferably has the meaning nC ₃ H ₇ .

The propylheptanol present in the alkoxylates can be prepared from valeraldehyde be obtained by aldol condensation and subsequent hydrogenation. The production of valeraldehyde and the corresponding isomers by hydroformylation of Butene, as described, for example, in US 4,287,370; Beilstein E IV 1, 32 68, Ullmanns Encyclopedia of Industrial Chemistry, 5th Ed., Vol. A1, pp. 323 and 328f. The subsequent aldol condensation is described, for example, in US Pat. No. 5,434,313 and US Pat Römpp, Chemie Lexikon, 9th edition, keyword "Aldol addition" page 91. The Hydrogenation of the aldol condensation product follows general hydrogenation conditions.

Furthermore, 2-propylheptanol can be obtained by condensation of 1-pentanol (as a mixture the corresponding methylbutanols-1) in the presence of KOH at elevated temperatures be prepared, see, for. Marcel Guerbet, C.R. Acad Sci Paris 128, 511, 1002 (1899). Furthermore, Römpp, Chemie Lexikon, 9th edition, Georg Thieme Verlag Stuttgart, and the citations quoted there as well as Tetrahedron, Vol. 23, pages 1723 to 1733, to point.

The alkoxylates of the general formula (I) can be obtained according to the invention by reacting alcohols of the general formula C ₅ H ₁₁ CH (C ₃ H ₇ ) CH ₂ OH first with propylene oxide and then with ethylene oxide under alkoxylation conditions. Suitable alkoxylation conditions are described, for example, in Nikolaus Schonfeldt, Grenzflächenaktive Äthylenoxid adducts, Wissenschaftliche Verlagsgesellschaft mbH Stuttgart, 1984. The alkoxylation can be carried out, for example, using alkaline catalysts such as alkali metal hydroxides, alkali metal alkoxides. The use of these catalysts results in special properties, in particular the distribution of the degree of alkoxylation.

The alkoxylation may also be performed using a Lewis acid catalysis with the resultant specific properties, in particular in the presence of BF ₃ · H ₃ PO _4, BF ₃ dietherate, SbCl _5, SnCl ₄ × 2H ₂ O, DMC, hydrotalcite.

In this case, the excess alcohol can be distilled off, or the alkoxylate can by a two-step process can be won. Also the production of mixed Alkoxylates of, for example, EO and PO is possible, with the alkanol radical initially being Polyethylene oxide block and then connect an ethylene oxide block, or first an ethylene oxide block and then a propylene oxide block. preferred Reaction conditions are given below.

Preferably, the alkoxylation is catalyzed by strong bases which suitably in the form of an alkali hydroxide or alkaline earth metal hydroxide, usually in an amount from 0.1 to 1% by weight, based on the amount of alkanol. (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. In addition to Bronsted acids are suitable for Lewis acids such. B. AlCl ₃ or BF ₃ . (See PH Plesch, The Chemistry of Cationic Polymerization, Pergamon Press, New York (1963).

The addition reaction is carried out at temperatures of about 90 to about 240 ° C, preferably from 120 to 180 ° C, carried in a closed vessel. The alkylene oxide or the Mixture of different alkylene oxides is the mixture of inventive Alkanol (mixture) and alkali under the prevailing at the selected reaction temperature Supplied vapor pressure of the alkylene oxide mixture. If desired, that can Alkylene oxide be diluted with up to about 30 to 60% with an inert gas. This will be a added security against explosive polyaddition of the alkylene oxide.

If an alkylene oxide mixture is used, polyether chains are formed in which the different alkylene oxide units are practically distributed statistically. Variations in the Distribution of the building blocks along the polyether chain are due to different Reaction velocities of the components and can also be arbitrary continuous supply of an alkylene oxide mixture of programmable composition be achieved. Are the different alkylene oxides in succession to the reaction brought so obtained polyether chains, with a block-like distribution of the alkylene oxide Building blocks.

The length of the polyether chains varies randomly within the reaction product an average, which is substantially the resulting from the additional amount corresponds to stoichiometric value.

In general, the alkoxylation in the presence of basic catalysts such as KOH in Substance performed. However, the alkoxylation can also with the concomitant use of a Solvent be carried out. For the preparation of the alkoxylates according to the invention The alcohols are first with a suitable amount of propylene oxide and then reacted with an appropriate amount of ethylene oxide. This is a polymerization of Alkylene oxides initiated, which inevitably leads to a statistical distribution from homologues whose mean value is given here as n and m.

By the propoxylation according to the invention first carried out and only subsequent Ethoxylation, the content of residual alcohol in the alkoxylates can be reduced since Propylene oxide is more evenly added to the alcohol component. In contrast to For example, ethylene oxide reacts preferentially with ethoxylates such that at an initial Use of ethylene oxide for reaction with the alkanols both a broad Homologous distribution as well as a high content of residual alcohol result. The avoidance of larger amounts of residual alcohol present in the product is in particular from Odor beneficial. The alcohols used in the invention usually have a Self-odor, which are largely suppressed by the complete alkoxylation can. Alkoxylates obtained by conventional methods have a high inherent odor, which is disturbing for many applications.

It is according to the invention not necessary and not desirable that a large residual content alcohol is present in the alkoxylates according to the invention. According to one Embodiment of the invention, the alkoxylates and their mixtures are largely free of Alcohols.

The alkoxylates according to the invention show improved wetting on hard Surfaces, especially in comparison with corresponding alcohols, which are only ethoxylated were first ethoxylated and then propoxylated. Products first ethoxylated and then propoxylated show a largely the same Wetting behavior such as products that have only been ethoxylated, but the advantageous invention Network properties are not preserved.

The advantageous wetting behavior of the compounds according to the invention can for example, determined by measurements of the contact angle to glass, polyethylene oxide or steel become. The improved network behavior is followed by better performance especially fast cleaning processes. This is surprising, since by the Chain extension of the starting alcohol usually the dynamic and wetting Properties are reduced. With the alkoxylates according to the invention can thus the wetting speed of aqueous formulations can be increased. The Alkoxylates according to the invention can thus also be used as solobilizers, which in particular, the network capacity of network aids, even in diluted systems not negative but positive influence. They can increase the solubility of Netzhilfsmitteln be used in aqueous formulations containing nonionic surfactants contain. They serve in particular to increase the wetting speed in aqueous wetting agents.

Furthermore, the alkoxylates of the invention serve to reduce the Interfacial tension, for example in aqueous surfactant formulations. The diminished Interfacial tension can be determined, for example, by the pendant drop method. This also results in a better effect of the alkoxylates according to the invention than Emulsifier or co-emulsifier. The alkoxylates according to the invention can also be used for Reduction in interfacial tension at short times, usually below one Second or to accelerate the adjustment of the interfacial tension in aqueous Tensidformulierungen be used.

The present invention also relates to cleaning, wetting, coating, adhesive, Leather grease, moisturizing or textile treatment or cosmetic, pharmaceutical or crop protection formulations containing at least one as defined above Alkoxylate of the general formula (I) included. The means preferably contain 0.1 to 20 wt .-% of the alkoxylates. Hereinafter, preferred applications of the alkoxylates of the invention described in more detail.

• - Tensidformulierungen zur Reinigung harter Oberflächen: Geeignete Tensidformulierungen, die mit den erfindungsgemäßen Alkoxylaten additiviert werden können, sind beispielsweise in Formulating Detergents and Personal Care Products von Louis Ho Tan Tai, AOCS Press, 2000; beschrieben. Sie enthalten beispielsweise als weitere Komponenten Seife, anionische Tenside wie LAS oder Paraffinsulfonate oder FAS oder FAES, Säure wie Phosphorsäure, Amidosulfonsäure, Zitronensäure, Milchsäure, Essigsäure, andere organische und anorganische Säuren, Lösungsmittel wie Ethylenglykol, Isopropanol, Komplexbildner wie EDTA, NTA, MGDA, Phosphonate, Polymere wie Polyacrylate, Copolymere Maleinsäure-Acrylsäure, Alkalispender wie Hydroxide, Silicate, Carbonate, Parfümöle, Oxidationsmittel wie Perborate, Persäuren oder Trichloroisocyanursäure, Na oder K-dichloroisocyanurate, Enzyme; siehe auch Milton J. Rosen, Manilal Dahanayake, Industrial Utilization of Surfactants, AOCS Press, 2000 und Nikolaus Schönfeldt, Grenzflächenaktive Ethylenoxidaddukte. Hier sind auch Formulierungen für die anderen genannten Anwendungen im Prinzip abgehandelt. Es kann sich um Haushaltsreiniger wie Allzweckreiniger, Geschirrspülmittel für manuelles wie automatisches Geschirrspülen, Metallentfettung, Industrielle Applikationen wie Reinigungsmittel für die Nahrungsmittelindustrie, Flaschenwäsche, etc. handeln. Es kann sich auch um Druckwalzen- und Druckplattenreinigungsmittel in der Druckindustrie handeln. Geeignete weitere Inhaltsstoffe sind dem Fachmann bekannt.
• - Feuchthaltemittel, insbesondere für die Druckindustrie.
• - Kosmetische, pharmazeutische und Pflanzenschutzformulierungen. Geeignete Pflanzenschutzformulierungen sind beispielsweise in der EP-A-0 050 228 beschrieben. Es können für Pflanzenschutzmittel übliche weitere Inhaltsstoffe vorliegen.
• - Lacke, Beschichtungsmittel, Farben, Pigmentpräparationen sowie Klebstoffe in der Lack- und Folienindustrie.
• - Lederfettungsmittel.
• - Formulierungen für die Textilindustrie wie Egalisiermittel oder Formulierungen zur Garnreinigung.
• - Faserverarbeitung und Hilfsmittel für die Papier- und Zellstoffindustrie.
• - Metallverarbeitung wie Metallveredelung und Galvanobereich.
• - Lebensmittelindustrie.
• - Wasserbehandlung und Trinkwassergewinnung.
• - Fermentation.
• - Mineralverarbeitung und Staubkontrolle.
• - Bauhilfsmittel.
• - Emulsionspolymerisation und Herstellung von Dispersionen.
• - Kühl- und Schmiermittel.

The alkoxylates according to the invention are preferably used in the following ranges:

• Surfactant formulations for hard surface cleaning: Suitable surfactant formulations that can be additized with the alkoxylates of the present invention are described, for example, in Formulating Detergents and Personal Care Products by Louis Ho Tan Tai, AOCS Press, 2000; described. They contain, for example as further components soap, anionic surfactants such as LAS or paraffin sulfonates or FAS or FAES, acid such as phosphoric acid, sulfamic acid, citric acid, lactic acid, acetic acid, other organic and inorganic acids, solvents such as ethylene glycol, isopropanol, complexing agents such as EDTA, NTA, MGDA , Phosphonates, polymers such as polyacrylates, copolymers of maleic-acrylic acid, alkali donors such as hydroxides, silicates, carbonates, perfume oils, oxidizing agents such as perborates, peracids or trichloroisocyanuric acid, Na or K-dichloroisocyanurate, enzymes; See also Milton J. Rosen, Manilal Dahanayake, Industrial Utilization of Surfactants, AOCS Press, 2000, and Nikolaus Schonfeldt, Ethylene Oxide Adduct Surfactants. Here are also formulations for the other applications mentioned dealt with in principle. These may be household cleaners such as all-purpose cleaners, dishwashing detergents for both manual and automatic dishwashing, metal degreasing, industrial applications such as food cleaners, bottling, etc. It may also be printing roll and printing plate cleaning agents in the printing industry. Suitable further ingredients are known to the person skilled in the art.
• - Humectants, especially for the printing industry.
• - Cosmetic, pharmaceutical and plant protection formulations. Suitable crop protection formulations are described, for example, in EP-A-0 050 228. There may be other usual ingredients for crop protection products.
• - Paints, coatings, paints, pigment preparations and adhesives in the paint and film industry.
• - Leather grease.
• Formulations for the textile industry, such as leveling agents or formulations for yarn cleaning.
• - Fiber processing and auxiliaries for the paper and pulp industry.
• - Metalworking such as metal finishing and electroplating.
• - Food industry.
• - Water treatment and drinking water production.
• - fermentation.
• - Mineral processing and dust control.
• - Construction aids.
• - Emulsion polymerization and preparation of dispersions.
• - Coolants and lubricants.

Such formulations usually contain ingredients such as surfactants, scaffolding, scent and dyes, chelants, polymers and other ingredients. typical Formulations are described, for example, in WO 01/32820. More for different Applications of suitable ingredients are described in EP-A-0 620 270, WO 95/27034, EP-A-0 681 865, EP-A-0 616 026, EP-A-0 616 028, DE-A-42 37 178 and US 5,340,495 by way of example described.

In general, the alkoxylates of the invention can be used in all areas where the effect of surfactants is necessary.

The structures according to the invention have better properties than known structures Environmental and skin compatibility, making it suitable for a variety of Application areas are advantageously suitable.

The invention is further illustrated by the following examples.

Preparation of the alkoxylates example 1 2-propylheptanol + 1.5 PO + 6 EO

790 g of 2-propylheptanol are treated with 8.5 g of KOH, 45% in water, in an autoclave submitted and dehydrated together at 80 ° C and reduced pressure (about 20 mbar). Then be added at 120 to 130 ° C 518 ml of propylene oxide and at this temperature Let it react under elevated pressure. The end of the reaction may be due to the pressure change to be watched. Subsequently, 1470 ml of ethylene oxide at 145 to 155 ° C over dosed for a longer time at elevated pressure and also allowed to reactivate. After rinsing with inert gas and cooling to room temperature, the catalyst is added by adding 3.8 ml of glacial acetic acid neutralized.

Example 2 2-propylheptanol + 1.5 PO + 8 EO

Reaction as in Example 1, the alkoxylation of 2-propylheptanol was carried out after Addition of 45% KOH and subsequent dehydration at about 80 ° C with propylene oxide and then with ethylene oxide in the appropriate stoichiometric ratios Conditions as given in Example 1. The neutralization was analogous to that Example 1 performed.

Example 3 2-propylheptanol + 1.5 PO + 10 EO

630 g of 2-propylheptanol are mixed with 9.1 g of KOH, 45% in water, in an autoclave submitted and dehydrated together at 80 ° C and reduced pressure (about 20 mbar). Then are added at 120 to 130 ° C 414 ml of propylene oxide and at this temperature Let it react under elevated pressure. The end of the reaction may be due to the pressure change to be watched. Subsequently, 1990 ml of ethylene oxide at 145 to 155 ° C over dosed for a longer time at elevated pressure and also allowed to reactivate. After rinsing with inert gas and cooling to room temperature, the catalyst is added by adding 4.0 ml of glacial acetic acid neutralized.

Comparative Example C1 2-propylheptanol + 8 EO

Reaction as in Example 1; on the reaction with PO at lower temperature was omitted, and 2-propylheptanol was reacted directly at 145-155 ° C with 8 moles of EO; the neutralization was carried out analogously to Example 1.

Comparative Example V2 2-propylheptanol + 8 EO + 1.5 PO

Reaction as in Example 1; but 2-propylheptanol was first added with 8 moles of EO Reacted 145-155 ° C and then reacted with 1.5 mol PO at 120-130 ° C; the neutralization was carried out analogously to Example 1.

applications

The alkoxylates according to the invention and the comparative alkoxylates were wetted used by glass, polyethylene and steel. The contact angle at a Concentration of 0.2 g / l measured in water at a temperature of 40 ° C. The Results are summarized in the tables below.

Interfacial tension

The interfacial tension was measured at 1 g / L at 25 ° C in hexadecane and olive oil. The measurement was carried out according to the pendant drop method. The results are also summarized in the following tables. Contact angle on V2A steel, [degrees]

Contact angle on polyethylene [degrees]

Contact angle on glass [degrees]

Wetting on cotton, EN 1 / 72,23, 0,1 g / l, 2 g / l soda in dist. water

Residual alcohol 2-PH, by gas chromatography with internal standard

Surface tension, pendant drop method, 1 g / l, 25 ° C, values after 10 min.

Example 2 Contact angle on V2A steel, [degrees]

Contact angle on polyethylene [degrees]

Contact angle on glass [degrees]

Wetting on cotton, EN 1772, 23 ° C, 1 g / l, 2 g / l soda in dist. water

Residual alcohol 2-PH, determined by gas chromatography with internal standard

Granule surface tension, pendant drop method, 1 g / l, 25 ° C, values after 10 min

The smaller the contact angle and the shorter the time for its adjustment, the better the network. The smaller the interfacial tension, the larger the Interfacial activity and emulsifying power.

Claims (10)

1. Use of alkoxylates of the general formula (I)

C ₅ H ₁₁ CH (C ₃ H ₇ ) CH ₂ O (A) _n (CH ₂ CH ₂ O) _m H (I)

with the meaning
A propyleneoxy, butenoxy or pentenoxy,
n number in the range of 1 to 8,
m number in the range of 2 to 20,
as emulsifier, foam regulator and wetting agent for hard surfaces. 2. Use according to claim 1 in surfactant formulations for cleaning hard Surfaces in humectants, cosmetic, pharmaceutical and Crop protection formulations, paints, coatings, adhesives, leather fatliquors, Formulations for metalworking, food industry, Water treatment, paper industry, fermentation, mineral processing and in Emulsion polymerization. 3. Use according to claim 1 or 2, characterized in that in the general formula (I) n is a number in the range of 1 to 6 and m is a number in the range of 3 until 14 is. 4. Use according to one of claims 1 to 3, characterized in that in the general formula (I) the radical C ₅ H _{11 is} nC ₅ H ₁₁ , C ₂ H ₅ CH (CH ₃ ) CH ₂ or CH ₃ CH (CH ₃ ) CH ₂ CH ₂ or mixtures of two or more of these compounds. 5. Alkoxylate of the general formula (I)

C ₅ H ₁₁ CH (C ₃ H ₇ ) CH ₂ O (A) _n (CH ₂ CH ₂ O) _m H (I)

with the meaning
A propyleneoxy, butenoxy or pentenoxy,
n is in the range of 1.2 to 1.8 when A is butoxy, from 1 to 1.8,
m number in the range of 3 to 14. 6. Alkoxylate according to claim 5, characterized in that in the general Formula (I) n is a number in the range of 1.3 to 1.7 and m is a number in the range of 3 to 12 mean. 7. Alkoxylate according to claim 5 and 6, characterized in that in the general formula (I) the radical C ₅ H _{11 is} nC ₅ H ₁₁ , C ₂ H ₅ CH (CH ₃ ) CH ₂ or CH ₃ CH (CH ₃ ) CH ₂ CH ₂ or mixtures of two or more of these compounds. 8. A process for the preparation of alkoxylates according to any one of claims 5 to 7 by reacting alcohols of the general formula C ₅ H ₁₁ CH (C ₃ H ₇ ) CH ₂ OH first with propylene oxide and then with ethylene oxide under alkoxylation. 9. The method according to claim 8, characterized in that the alcohols of the general formula C ₅ H ₁₁ CH (C ₃ H ₇ ) CH ₂ OH are obtained by alkaline dimerization of valeraldehyde to an α, β-unsaturated aldehyde and subsequent hydrogenation. 10. cleaning, wetting, coating, adhesive, leather grease, moisturizing or Textile treatment or cosmetic, pharmaceutical or Crop protection formulation containing at least one alkoxylate of the general formula (I) as described in one of claims 1 to 7 is defined.