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WO1996011177A1 - Matieres grasses - Google Patents

Matieres grasses Download PDF

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Publication number
WO1996011177A1
WO1996011177A1 PCT/DE1995/001356 DE9501356W WO9611177A1 WO 1996011177 A1 WO1996011177 A1 WO 1996011177A1 DE 9501356 W DE9501356 W DE 9501356W WO 9611177 A1 WO9611177 A1 WO 9611177A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
octanol
manner known
known per
octylpropylene
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.)
Ceased
Application number
PCT/DE1995/001356
Other languages
German (de)
English (en)
Inventor
Karl Schmid
Michael Neuss
Michael Nitsche
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
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to EP95934041A priority Critical patent/EP0785918A1/fr
Publication of WO1996011177A1 publication Critical patent/WO1996011177A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
    • 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
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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

  • the invention relates to new fatty substances, a process for the production of the fatty substances by propoxylation of octanol and then removal of free fatty alcohol, processes for the production of surface-active derivatives of these fatty substances and the use of the fatty substances and their derivatives for the production of surface-active agents.
  • WO 94/11487 discloses the use of undecyl alcohol to improve the performance of powdered detergents containing alkyl sulfate.
  • the invention relates to fatty substances of the formula (I)
  • R 1 represents a linear or branched alkyl radical having 8 carbon atoms, with the hate that the proportion of free octanol is less than 5, preferably less than 1% by weight.
  • the fatty substances according to the invention have advantageous cold behavior.
  • octylpropylene glycol ethers are mixed with other anionic and / or nonionic surfactants, a lower viscosity (liquid products) and an increased dissolution rate and detergency (solid products) are observed;
  • an improvement in the dermatological properties can be determined, which makes it possible to produce highly concentrated, high-performance products which are nevertheless classified as low irritation.
  • the invention includes the knowledge that these surprising properties relate both to the chosen chemical 96/11177 " 4 " PCIYDE95 / 01356
  • the inventive idea also includes the knowledge that the improved application properties are not limited to octylpropylene glycol ethers, but are also retained in the typical secondary products such as sulfates, ethoxylates and ether sulfates. Octylpropylene glycol ethers are also interesting chemical intermediates.
  • the invention further relates to a process for the preparation of fatty substances of the formula (I),
  • R 1 represents a linear or branched alkyl radical having 8 carbon atoms, which is characterized in that octanol is etherified with propylene oxide in a manner known per se and then the proportion of unreacted alcohol is distilled to a value of less than 5 , preferably less than 1% by weight.
  • octylpropylene glycol ethers (“octanol + IPO”) are prepared in a manner known per se, preferably by reacting 1 mol of 2-ethylhexanol and in particular n-octanol with 1 mol of propylene oxide in the presence of alkaline catalysts (for example sodium methylate) at 120 to 180 ° C in a pressure vessel under autogenous pressure.
  • alkaline catalysts for example sodium methylate
  • the invention further relates to a process for the preparation of fatty substances of the formula (II),
  • R 1 is a linear or branched alkyl radical having 8 carbon atoms and X is an alkali metal and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium, characterized in that
  • the sulfation of the octylpropylene glycol ethers can take place in the manner known for fatty acid lower alkyl esters [J. Falbe (ed.), "Surfactants in consumer products", Springer Verlag, Berlin-Heidelberg, 1987, p. 61], with reactors working according to the falling film principle , are preferred.
  • Chlorosulfonic acid and in particular gaseous sulfur trioxide are suitable as sulfonating agents.
  • the latter is usually diluted with an inert gas, preferably air or nitrogen, and used in the form of a gas mixture which contains the sulfonating agent in a concentration of 1 to 8, in particular 2 to 5,% by volume.
  • the molar ratio of ether to sulfating agent can be 1: 0.9 to 1: 1.3 and preferably 1: 0.95 to 1: 1.05.
  • the sulfation is usually carried out at temperatures from 20 to 50 ° C. With regard to the viscosity of the starting materials on the one hand and the color quality of the resulting sulfation products on the other hand, it has proven to be optimal to carry out the reaction in a temperature range from 25 to 35 ° C.
  • the acidic sulfonation products obtained in the sulfation are stirred into aqueous bases, neutralized and adjusted to a pH of 6.5 to 8.5.
  • bases for the neutralization come alkali metal hydroxides such as sodium, potassium and lithium hydroxide, alkaline earth metal oxides and hydroxides such as magnesium oxide, magnesium hydroxide, calcium oxide and calcium hydroxide, ammonia, mono-, di- and tri-C2_4 * -alkanolamines, for example mono -, di- and triethanolamine as well primary, secondary or tertiary C1-.4- alkylanu.ne as well as glucamines.
  • the neutralization bases are preferably used in the form of 5 to 55% by weight aqueous solutions, 5 to 25% by weight aqueous sodium hydroxide solutions being preferred.
  • the sulfation products can be bleached in a manner known per se by adding hydrogen peroxide or sodium hypochlorite solution. Based on the solids content in the solution of the sulfation products, 0.2 to 2% by weight of hydrogen peroxide, calculated as a 100% substance, or corresponding amounts of sodium hypochlorite are used.
  • the pH of the solutions can be adjusted using suitable buffering agents, e.g. B. be kept constant with sodium phosphate or citric acid. To stabilize against bacterial contamination, a preservation is also recommended, e.g. B. with formaldehyde solution, p-hydroxybenzoate, sorbic acid or other known preservatives.
  • the invention further relates to a process for the preparation of fatty substances of the formula (III),
  • the ethoxylation of the octylpropylene glycol ethers can be carried out in the presence of acidic, but preferably alkaline, catalysts such as sodium methylate, potassium hydroxide and the like. If products with a narrow homolog distribution are desired, the use of stontium or barium salts and in particular of calcined hydrotalcites or those hydrophobicized with fatty acids is appropriate.
  • the reaction is usually carried out at temperatures in the range from 120 to 150 and preferably 140 to 160 ° C. and an autogenous pressure in the range from 1 to 5 bar.
  • phosphoric acid or lactic acid is generally added to the products.
  • the invention further relates to a process for the production of fatty substances of the formula (TV),
  • R stands for a linear or branched alkyl radical with 8 carbon atoms, n for numbers from 1 to 10 and X for an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium, which is characterized in that
  • etherifying octanol with propylene oxide in a manner known per se b) if appropriate, the amount of unreacted alcohol is reduced by distillation to a value of less than 5% by weight, c) the octylpropylene glycol ether in a manner known per se with an average of 1 to 10 moles of ethylene oxide are reacted, d) the resulting octylpropylene glycol (poly) ethylene glycol ether is sulfated in a manner known per se and finally e) neutralized with bases.
  • the ether sulfates are prepared analogously to the teaching in Chapter "fatty alcohol sulfates and H fatty alcohol ethoxylates H.
  • octylpropylene glycol ethers After free octanol has been separated off, octylpropylene glycol ethers have a particularly advantageous low-temperature behavior. They enable the production of low-viscosity liquid detergent concentrates and improve the dissolution rate of powder detergents containing alkyl sulfate. Derivatives of these ethers, in particular sulfates, ethoxylates and ether sulfates, which are collectively subsumed under the term "fatty substances”, have interesting surface-active properties, such as, for example, a reduced tendency to crystallize or improved dermatological compatibility, on their own, but especially when mixed with other surfactants.
  • Another object of the invention finally relates to the use of the fatty substances mentioned for the production of surface-active agents such as, for example, powder detergents, liquid detergents, hand dishwashing detergents, hand washing pastes, all-purpose cleaners, agents for machine bottle cleaning and agents for degreasing metal surfaces.
  • surface-active agents such as, for example, powder detergents, liquid detergents, hand dishwashing detergents, hand washing pastes, all-purpose cleaners, agents for machine bottle cleaning and agents for degreasing metal surfaces.
  • the octyl propylene glycol ethers and their sulfates, ethoxylates and / or ether sulfates with anionic surfactants of the fatty alcohol sulfate type (“alkyl sulfates”) and / or fatty alcohol ether sulfates (“ether sulfates”) and nonionic surfactants of the type the fatty alcohol polyglycol ether, mixed ether and alkyl oligoglucoside are mixed.
  • the mixtures can be prepared by known processes from the prior art. If an octylpropylene glycol sulfate or ether sulfate is mixed with another fatty alcohol sulfate or ether sulfate, cosulfation of the starting materials is appropriate.
  • Anionic surfactant content 27% by weight unsulfated 3% by weight sodium sulfate 1% by weight water 69% by weight
  • the anionic surfactant content (WAS) and the unsulfonated proportions (US) were determined according to the DGF standard methods, Stuttgart 1950-1984, H-III-10 and G-II-6b.
  • the Klett color number was determined after 30 minutes of bleaching with 1% by weight of a 35% by weight aqueous hydrogen peroxide solution. The measurement was carried out at a concentration of 5% by weight of anion surfactant, pH ⁇ 7 and using a 1 cm round cuvette and a blue filter (400 to 465 nm).
  • Example Hlb Analogously to Example Hlb), 186 g (1 mol) of purified octyl propylene glycol ether were placed in an autoclave with 2.7 g of sodium methylate and 88 g (2 mol) of ethylene oxide were reacted.
  • the octylpropylene glycol-2EO adduct was obtained as a colorless liquid in virtually quantitative yield.
  • Anionic surfactant content 31% by weight unsulfated 4% by weight sodium sulfate 1% by weight water 64% by weight
  • Example nonionic surfactant distills KTP
  • the surfactant compound can be classified as "low irritation” and has a 25% improvement in crystallization inhibition compared to pure Texapon ( R ) N70.
  • the compound is suitable for the production of hand dishwashing detergents.
  • the dissolution rate in cold water (20 ° C) is improved by 35% and 25%, respectively.
  • the compounds are suitable, for example, for producing hand washing pastes
  • the surfactant compound can be granulated or extruded together with 20% by weight of zeolite A, based on the total mixture, to give a dry powder which has a 25% better dissolution than pure sulfopon ( R ) 1218 W / zeolite powder. speed in cold water (20 ° C) and has a 10% improved washing performance. In addition, the powder is significantly drier.
  • the surfactant compound has a very low viscosity (according to Brookfield, RTV viscometer, 20 ° C, spindle 1, 10 rpm) of approx. 300 Pas and can be used as a liquid detergent.
  • a very low viscosity according to Brookfield, RTV viscometer, 20 ° C, spindle 1, 10 rpm
  • Lorol ( R ) T7 a cut-resistant gel is obtained.
  • the surfactant compound is suitable as a low-foaming wetting agent for the spray cleaning of body panels.

Landscapes

  • 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)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne de nouvelles matières grasses de formule (I), où R1 représente un radical alkyle linéaire ou ramifié avec 8 atomes de carbone, à condition que la teneur en octanol libre soit inférieure à 5 % en poids. Les octylpropylèneglycoléthers ainsi que les sulfates, éthoxylates et sulfates d'éther, qui en sont dérivés, se distinguent par des propriétés d'utilisation améliorées.
PCT/DE1995/001356 1994-10-10 1995-10-02 Matieres grasses Ceased WO1996011177A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP95934041A EP0785918A1 (fr) 1994-10-10 1995-10-02 Matieres grasses

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4436066.5 1994-10-10
DE19944436066 DE4436066A1 (de) 1994-10-10 1994-10-10 Fettstoffe

Publications (1)

Publication Number Publication Date
WO1996011177A1 true WO1996011177A1 (fr) 1996-04-18

Family

ID=6530323

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE1995/001356 Ceased WO1996011177A1 (fr) 1994-10-10 1995-10-02 Matieres grasses

Country Status (3)

Country Link
EP (1) EP0785918A1 (fr)
DE (1) DE4436066A1 (fr)
WO (1) WO1996011177A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007534669A (ja) * 2004-02-12 2007-11-29 ビーエーエスエフ　アクチェンゲゼルシャフト アルキルエーテル硫酸塩
CN111263748A (zh) * 2017-11-10 2020-06-09 阿科玛法国公司 烷氧基化仲醇硫酸酯

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4275723B2 (ja) 2007-07-09 2009-06-10 花王株式会社 界面活性剤組成物
JP4246252B2 (ja) 2007-07-10 2009-04-02 花王株式会社 界面活性剤組成物
JP5242147B2 (ja) * 2007-12-11 2013-07-24 花王株式会社 界面活性剤組成物
FR3073521A1 (fr) 2017-11-10 2019-05-17 Arkema France Ester de phosphate d'alcool secondaire
FR3073519B1 (fr) 2017-11-10 2025-09-19 Arkema France Alcool secondaire alcoxyle

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4243643C1 (fr) * 1992-12-22 1993-08-26 Henkel Kgaa, 4000 Duesseldorf, De
WO1994011487A1 (fr) * 1992-11-16 1994-05-26 Unilever Plc Compositions detergentes

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4727199A (en) * 1985-07-10 1988-02-23 Union Carbide Corporation Heterogeneous alkoxylation using anion-bound metal oxides
US4721817A (en) * 1986-12-31 1988-01-26 Shell Oil Company Preparation of nonionic surfactants
DD292146A5 (de) * 1988-05-09 1991-07-25 ������@������������k�� Nichtionogenes netzmittel fuer schwerbenetzbare staeube
DE4110178A1 (de) * 1991-03-27 1992-10-01 Henkel Kgaa Verbessertes verfahren zur herstellung von nichtionischen oberflaechenaktiven verbindungen
DE4237178A1 (de) * 1992-11-04 1994-05-05 Henkel Kgaa Wäßriges Tensidkonzentrat

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994011487A1 (fr) * 1992-11-16 1994-05-26 Unilever Plc Compositions detergentes
DE4243643C1 (fr) * 1992-12-22 1993-08-26 Henkel Kgaa, 4000 Duesseldorf, De

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
H. C. CHITWOOD ET AL: "The reaction of propylene oxide with alcohols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 68, DC US, pages 680 - 683 *
J. CHLEBICKI ET AL: "Synthesis and surface activity of sodium polyoxypropylated higher alcohol sulphates", TENSIDE DETERGENTS, vol. 17, no. 3, pages 130 - 134 *
J. OTERA ET AL: "Highly regioselective ring opening of epoxides with alcohols catalyzed by organotin phosphate condensates", TETRAHEDRON LETTERS, vol. 26, no. 27, OXFORD GB, pages 3219 - 3222 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007534669A (ja) * 2004-02-12 2007-11-29 ビーエーエスエフ　アクチェンゲゼルシャフト アルキルエーテル硫酸塩
CN111263748A (zh) * 2017-11-10 2020-06-09 阿科玛法国公司 烷氧基化仲醇硫酸酯
JP2021502369A (ja) * 2017-11-10 2021-01-28 アルケマ フランス アルコキシル化第二級アルコール硫酸塩

Also Published As

Publication number Publication date
EP0785918A1 (fr) 1997-07-30
DE4436066A1 (de) 1996-04-11

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