EP0442924A1 - Melanges d'alcools gras et leurs ethoxylates a comportement a froid ameliore - Google Patents

Melanges d'alcools gras et leurs ethoxylates a comportement a froid ameliore

Info

Publication number
EP0442924A1
EP0442924A1 EP89912442A EP89912442A EP0442924A1 EP 0442924 A1 EP0442924 A1 EP 0442924A1 EP 89912442 A EP89912442 A EP 89912442A EP 89912442 A EP89912442 A EP 89912442A EP 0442924 A1 EP0442924 A1 EP 0442924A1
Authority
EP
European Patent Office
Prior art keywords
ethoxylates
fatty alcohol
mixtures
alcohol
fatty
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP89912442A
Other languages
German (de)
English (en)
Inventor
Karl-Heinz Schmid
Hans Peter Kubersky
Günter DEMMERING
Alfred Meffert
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6366775&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0442924(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0442924A1 publication Critical patent/EP0442924A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/02—Monohydroxylic acyclic alcohols
    • C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
    • 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
    • C07C43/14—Unsaturated ethers
    • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • 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

Definitions

  • alkyl or alkylaryl polyglycol ethers as nonionic surfactants have become increasingly important as formulation constituents of detergents and cleaning agents and as constituents of emulsifiers in cosmetic or technical preparations.
  • the basis for the synthesis of such non-ionic surfactants are alkylphenols, oxo alcohols according to the high-pressure (Roelen process) or low-pressure (shop process) hydroformulation processes, alcohols according to the Ziegler process and fatty alcohols, such as those used for. B. can be obtained by hydrogenating natural oils and fats or from the native fatty acids or their methyl esters produced therefrom.
  • Alkyl polyglycol ethers based on oxo alcohols as well as Ziegler and fatty alcohols are becoming increasingly important due to their more favorable ecotoxic properties compared to alkyl phenol polyglycol ethers. Since most technical emulsifiers are used in liquid formulations, one of the most important requirements for nonionic surfactants has always been the lowest possible pour point. This demand for non-ionic surfactants with sufficiently good cold behavior has increased in recent years in particular by the fact that liquid formulations have found their way into product areas where previously only powder formulations were known. The area of detergents and cleaning agents, especially textile detergents, should be mentioned here in particular.
  • the ethoxylates of oxoalcohols branched in their basic structure are superior to those based on linear alcohols - in particular Ziegler alcohols and fatty alcohols - with the same carbon chain length of the alkyl part and the same number of ethylene oxide units in the molecule.
  • the pour point of an alcohol, as well as the ethoxylate produced from it the lower the branched the structure of the alcohol.
  • alkyl ethoxylates with an average of about 5 to 10 moles of ethylene oxide, based on 1 mole of alcohol, where the alcohol in particular has a carbon chain length of about 12 to 15.
  • Compounds of this type are distinguished by particularly good washing, wetting, emulsifying and cleaning properties.
  • Compounds of this type based on currently available fatty alcohols of native origin of comparable carbon chain lengths and the same proportion of ethylene oxide in the molecule are inferior to the corresponding compounds based on oxo alcohols in terms of low-temperature behavior.
  • the invention seeks a technically better solution compared to dealing with this problem today.
  • coconut oil, Paimkern ⁇ in particular come as natural raw material sources for a fatty alcohol which has the carbon chain length C 12 to C 14 described above in terms of application technology. and babassu oil in question.
  • a disadvantage of these oils is, however, that the fatty alcohols obtained therefrom - particularly in the case of palm kernel oil and babassu oil - still contain considerable amounts of undesired C 16 / C 18 components, which lead to unsatisfactory low-temperature behavior in the ethoxylates prepared therefrom.
  • fatty alcohols or fatty alcohol fractions are obtained from fats and / or oils of vegetable origin
  • the fatty ureat mixtures obtained from the vegetable raw materials are reduced as the fatty acid methyl ester under process conditions to the corresponding alcohols under hydrogenation conditions, in which not only the reduction the carboxyl function, but also the extensive saturation of chain olefinic double bonds takes place.
  • the teaching of the invention is based on the finding that fatty alcohols and ethoxylates produced from these fatty alcohols can be produced with significantly better low-temperature behavior from the same vegetable raw materials, if the chain-linked, partially olefinic structure of these starting materials is changed as little as possible and instead is changed limited to a selective reduction of the carboxy function.
  • the fatty alcohol fractions obtained in this way which in their composition of the hydrocarbon residues are as similar as possible to the type of vegetable oils used or the fatty acid mixtures present therein, are distinguished by a significantly improved cold behavior.
  • the invention accordingly relates to a first
  • the fatty alcohol mixtures of specification I can be of particular importance if the ratio of the simple olefinically unsaturated hydrocarbon radical having 18 carbon atoms to the sum of the single and double olefinically unsaturated hydrocarbon residues, each with 18 carbon atoms, is greater than 78%.
  • Preferred fatty alcohol mixtures of the previously specified specifications are preferably of purely vegetable origin or, respectively, by selective hydrogenation of corresponding mixtures of fatty acids of natural origin. accessible by the selective hydrogenation of corresponding ester mixtures of such fatty acids.
  • Particularly suitable esters for this selective hydrogenation are corresponding esters with monofunctional alcohols, in particular lower monohydric alcohols with 1 to 5 carbon atoms. As is well known, the methyl ester and, to a certain extent, the butyl ester are of particular importance.
  • the selective hydrogenation is carried out while maintaining the natural distribution of the saturated and the mono- and poly-olefinically unsaturated hydrocarbon residues in the feed material as far as possible.
  • Particularly suitable feedstocks of purely vegetable origin are coconut oil, palm kernel oil, babassu oil and rocca fat or the fatty acid mixtures obtained therefrom and in particular the corresponding fatty acid methyl ester mixtures.
  • Fatty alcohol mixtures of the aforementioned Specification I still contain the lower fractions from C 6 to C 10, which can be odorlessly undesirable in certain areas of application.
  • the invention accordingly comprises the alcohol mixtures of the aforementioned Specification II, which can be easily obtained from the substance mixtures of the aforementioned Specification I by removing the C 6 to C 10 fraction.
  • both fatty alcohol mixtures and in particular the ethoxylates described according to the invention obtained therefrom are notable for their considerable content, in particular of C 16 / C 18 components.
  • the content according to the invention of this fraction of mono- and poly-olefinically unsaturated components nevertheless, the desired goal of cold stability comparable to the oxo alcohols or their derivatives is certain, without substantial material losses of the renewable feed material having to be accepted.
  • the ethoxylates of particular interest here are also completely satisfactory in the other technical properties.
  • the invention relates to the use of fatty alcohol mixtures R. -OH where the
  • Rest level specifications I or II speaks for the production of ethoxylates with improved flowability at low temperatures, especially in the room temperature range. These ethoxylates correspond to the all-e has the given meaning and x is a number from 2 to 10, preferably from 3 to 9.
  • the ethoxylates are prepared from the fatty alcohol mixtures defined according to the invention in a manner known per se by reacting the alcohol mixtures with ethylene oxide, either with alkaline or acidic catalysis.
  • Alkaline catalysis is widespread in the industrial process, although sodium methylate, but also sodium hydroxide, sodium, sodium ethylate, potassium hydroxide, etc. are generally used as catalysts.
  • the reaction is exothermic through the ring opening.
  • the reaction temperature is for example in the range of about 135 to 150 C.
  • the reaction product is then mixed with inorganic or organic acids, for. B. neutralized with acetic acid anhydride, phosphoric acid or carbon dioxide.
  • the resulting ethoxylation product is not uniform, rather polymer homologs are obtained.
  • the distribution curve differs depending on the type of catalysis.
  • the reaction conditions can be chosen much more drastically. For example, you can work at 50 to 70 atm and 250 to 350 C.
  • the invention relates to the use of ethoxylates of selected fatty alcohol mixtures of natural, preferably purely vegetable, origin with the an -H, in the R. -
  • the specifications I or II given above and x means on average a number from 2 to 10, preferably from 3 to 9, as a surfactant component with improved low-temperature behavior.
  • Ethoxylates of the type described here are distinguished, in particular in the area of room temperature, by their presence as a homogeneous liquid phase, also with good flow properties. Even if surfactant mixtures of the type in question are solidified by supercooling, such materials melt again in a short time when the room temperature is adjusted to the easily pourable homogeneous liquid phase.
  • nonionic surfactant component For the use of these materials as a nonionic surfactant component, there are considerable advantages in everyday use in many fields of application. Not only is it easier to handle.
  • Such reaction products can still be flowable, but their batch processing from a storage container is understandably difficult. It is required before removal a portion of the material carefully homogenized the contents of the container in order to reliably rule out any shifts in the composition of the complex reaction product.
  • the ethoxylates preferred according to the invention are present in the region of the room temperature as a homogeneous liquid phase in which segregation processes are eliminated from the outset. This ensures a quantity that is not restricted in terms of quantity and, in some cases, material removal with constant product properties.
  • the teaching of the invention combines the new measures for improving the cold resistance of fatty alcohol ethoxylates of the type described with the teaching of the earlier application P 3802027.0 (D 8083) by the applicant.
  • This earlier application describes a process for the preparation of alkyl polyglycol ethers with improved cold behavior by reacting saturated and / or unsaturated, in particular straight-chain alcohols with ethylene oxide at elevated temperatures in the presence of basic alkali metal compounds as catalysts and subsequent neutralization of the alkaline Catalyst with organic and / or inorganic acids.
  • the characteristic of the teaching from this earlier protective right is that one works with such increased catafyzator concentrations that salt precipitation occurs as an undissolved solid phase in the neutralization step and that the neutralization step is carried out in such a way that the salt phase is precipitated in the presence of im Reaction product disperses finely divided solids.
  • This teaching of the earlier application is based on the task of making fatty alcohol ethylene oxide adducts with improved low-temperature stability accessible without a deterioration in the other application properties in a technically simple process.
  • the technical solution to this task works based on the knowledge that a substantial increase in the amount of basic alkali metal catalysts in the ethoxylation step can result in substantial improvements in the material parameters characterizing the cold stability without undesirably increasing the application properties such as washing or wetting properties, emulsifying properties and the like affect.
  • the amount of the basic catalyst must be increased beyond the limit which characterizes the solubility of the salt obtained by neutralization in the ethoxylation product.
  • finely divided solids for precipitating the salt phase in the reaction product preference is given to using organic and / or inorganic filter aids which are dispersed in the alkyl polyglycol ether reaction product before the salt phase crystallizes out.
  • the finely divided filter aids are preferably used in amounts of about 0.3 to 2% by weight, in particular in amounts of about 0.5 to 1% by weight, based in each case on the alkyl polyglycol ether formed.
  • Mixtures of inorganic and organic material preferably in the range of about 3: 1 to 1: 3, can in particular be used as filter aids.
  • a suitable inorganic filter aid is, for example, diatomaceous earth, organic filter aids are, for example, wood flour and / or finely powdered cellulose.
  • partial neutralization for example up to about pH 8
  • bleaching is carried out by adding, in particular, hydrogen peroxide, whereupon the full neutralization of the reaction product to pH values in the range of about 6, 5 to 7.5 is made.
  • the neutralization stage and precipitation of the salt phase on the surface of the dispersed filter aid are preferably carried out in the temperature range from about 50 to 110.degree.
  • the amounts of basic catalyst used for the ethoxylation of the sterically unhindered alcohols in this process are generally at least about 0.5% by weight, calculated as sodium methylate and based on the total mixture of alcohol and ethylene oxide, with amounts in the range from about 0.5 to 1.5% by weight, and in particular those in the range from about 0.8 to 1.1% by weight, can be particularly preferred.
  • the technical teaching is not restricted to working with sodium methylate.
  • Other known basic alkali metal catalysts can also be used in equivalent proportions.
  • the neutralization of the catalyst in the reaction product is carried out with organic and / or inorganic acids.
  • Examples include gluconic acid, glycolic acid, acetic acid, formic acid, benzoic acid, lactic acid, oxalic acid, citric acid, propionic acid, phosphoric acid, methanesulfonic acid and / or diglykoic acid. Strongly corrosive acids, for example sulfuric acid or hydrochloric acid, are of no importance in practice.
  • the ethoxylate in which the filter aid and the salt formed are homogeneously distributed, is pumped to the filtration stage.
  • the filtration can take place both through flow filters and through filter presses and through rotary filters. Particularly low-salt ethoxylates are obtained if the filtration under nitrogen is carried out at temperatures higher than 80 ° C.
  • the amounts of fatty alcohol, ethylene oxide and catalyst given in the examples are approx. 3 to 4 in an autoclave at 170 to 180 ° C. with a reaction pressure of 2 to a maximum of 5 bar Hours implemented.
  • the fatty alcohol ethoxylate is transferred to a neutralization container equipped with a stirrer and the product is neutralized at 90 ° C. with lactic acid, so that the reaction product finally has a pH (1% of the product in 99% deionized water ) from 6.5 to 7.5.
  • the amount of sodium methylate used for the alkoxylation reaction exceeds 0.5% by weight, the alkoxylation product becomes after addition of a maximum of 1% by weight of filter aid and subsequent neutralization filtered with lactic acid.
  • Turbidity temperature, turbidity titration number of the ethoxylate takes place according to D IN 53917.
  • Type I to Type IV The four coconut alcohols "Type I to Type IV" are used for the examples below. Types I and III correspond to the definition according to the invention, while types II and IV are largely free of olefinically unsaturated C 18 alcohols.
  • the product which corresponds to a fat-alcohol-7EO adduct, was cooled to -10 ° C. until it was solid. The product was then stored at 22 ° C. for 1 week. After that time the product was still solid.
  • the product which corresponds to a fatty alcohol 9EO adduct, was cooled to -10 ° C until solid. The product was then stored at 25 ° C. for 1 week. After that time the product was still solid.
  • the product which corresponds to a fatty alcohol koho-7EO adduct, was cooled to -10 ° C until solid. The product was then stored at 22 ° C. for 24 hours. After this time the product was liquid.

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

Abstract

Des mélanges d'alcools gras Rmix-OH d'origine naturelle, en particulier purement végétale, ainsi que leurs éthoxylates à comportement à froid amélioré correspondant à la formule générale Rmix-O-(CH2CH2O)x-H, où x représente un chiffre compris entre 2 et 10 et Rmix- des résidus alcools gras-hydrocarbures saturés et oléfiniquement insaturés des régions C 6 à 20 ou C 12 à 20, correspondent à la spécification (I) pour la région de longueur de chaîne Rmix = C 6 à 20 et à la spécification (II) pour la région de longueur de chaîne Rmix = C 12 à C 20.
EP89912442A 1988-11-09 1989-10-31 Melanges d'alcools gras et leurs ethoxylates a comportement a froid ameliore Pending EP0442924A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3837947A DE3837947A1 (de) 1988-11-09 1988-11-09 Neue fettalkoholgemische und ihre ethoxylate mit verbessertem kaelteverhalten
DE3837947 1988-11-09

Publications (1)

Publication Number Publication Date
EP0442924A1 true EP0442924A1 (fr) 1991-08-28

Family

ID=6366775

Family Applications (2)

Application Number Title Priority Date Filing Date
EP89120175A Expired - Lifetime EP0370273B2 (fr) 1988-11-09 1989-10-31 Ethoxylates d'alcools gras à caractéristiques modifiées à basse température
EP89912442A Pending EP0442924A1 (fr) 1988-11-09 1989-10-31 Melanges d'alcools gras et leurs ethoxylates a comportement a froid ameliore

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP89120175A Expired - Lifetime EP0370273B2 (fr) 1988-11-09 1989-10-31 Ethoxylates d'alcools gras à caractéristiques modifiées à basse température

Country Status (9)

Country Link
EP (2) EP0370273B2 (fr)
JP (1) JPH04501561A (fr)
KR (1) KR900701710A (fr)
AT (1) ATE87292T1 (fr)
BR (1) BR8907762A (fr)
DE (2) DE3837947A1 (fr)
DK (1) DK86691A (fr)
ES (1) ES2053910T3 (fr)
WO (1) WO1990005127A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA909267B (en) * 1990-03-09 1991-09-25 Ici Australia Operations Fatty alcohol alkoxylate
DE4205844A1 (de) * 1992-02-26 1993-09-02 Sandoz Ag Kondensate und deren verwendung als oxalkylierungshilfsmittel
WO1994014918A1 (fr) * 1992-12-28 1994-07-07 Henkel Kommanditgesellschaft Auf Aktien Preparations aqueuses coulantes pouvant etre pompees, dirigees de maniere rheologique pour servir par exemple de boues de forage a base d'eau
DE4335781C2 (de) * 1993-10-20 1998-02-19 Henkel Kgaa Fettalkohole auf pflanzlicher Basis und Verfahren zu Ihrer Herstellung
DE4422858C1 (de) * 1994-06-30 1995-07-27 Henkel Kgaa Ungesättigte Fettalkohole mit verbessertem Kälteverhalten
DE4425180C2 (de) * 1994-07-16 1997-05-07 Henkel Kgaa Verfahren zur Herstellung ungesättigter Fettalkohole oder deren veresterte, alkoxylierte und/oder sulfatierte Derivate mit verbessertem Kälteverhalten
DE10004678A1 (de) * 2000-02-03 2001-08-09 Cognis Deutschland Gmbh Tensidgranulate
DE102012223204A1 (de) * 2012-12-14 2014-06-18 Henkel Ag & Co. Kgaa Reduzierung des Ammoniakgeruchs in Mitteln zum oxidativen Färben und/oder Aufhellen von keratinischen Fasern

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1029502A (en) * 1910-03-11 1912-06-11 Joseph Margulies Landon Trumpet.
US2094127A (en) * 1932-01-02 1937-09-28 Du Pont Mixed higher alcohols
DE865741C (de) * 1939-09-06 1953-02-05 Hydrierwerke A G Deutsche Verfahren zur Herstellung von ungesaettigten Verbindungen durch katalytische Reduktion von ungesaettigten Fettsaeuren, deren Estern oder Anhydriden mit Wasserstoff oder wasserstoffhaltigen Gasen
DE965236C (de) * 1955-08-22 1957-06-06 Dehydag Gmbh Verfahren zur kontinuierlichen Herstellung einfach ungesaettigter, hoehermolekularerFettalkohole
DE1232950B (de) * 1963-06-07 1967-01-26 Kyowa Hakko Kogyo Kk Verfahren zur Herstellung von ungesaettigten Alkoholcn durch katalytische Hydrierungungesaettigter Fettsaeuren und/oder ungesaettigter Fettsaeureester
DE1628652B2 (de) * 1968-03-14 1977-07-14 Henkel & Qe GmbH, 4000 Dusseldorf Verfahren zum maschinellen spuelen von geschirr
DE2418294B2 (de) * 1974-04-16 1976-11-04 Henkel & Cie GmbH, 4000 Düsseldorf Pulverfoermiges bis koerniges, nichtionische waschaktivsubstanzen enthaltendes waschmittel
DE2513377C3 (de) * 1975-03-26 1985-08-29 Henkel KGaA, 4000 Düsseldorf Verfahren zur Herstellung einfach ungesättigter höhermolekularer Fettalkohole

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9005127A1 *

Also Published As

Publication number Publication date
KR900701710A (ko) 1990-12-04
EP0370273B1 (fr) 1993-03-24
WO1990005127A1 (fr) 1990-05-17
DK86691D0 (da) 1991-05-08
ATE87292T1 (de) 1993-04-15
DK86691A (da) 1991-05-08
EP0370273B2 (fr) 2000-07-12
DE3837947A1 (de) 1990-05-10
ES2053910T3 (es) 1994-08-01
EP0370273A1 (fr) 1990-05-30
JPH04501561A (ja) 1992-03-19
BR8907762A (pt) 1991-10-01
DE58903884D1 (de) 1993-04-29

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