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WO1997038968A1 - Synthese d'amines substituees - Google Patents

Synthese d'amines substituees Download PDF

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Publication number
WO1997038968A1
WO1997038968A1 PCT/US1997/006337 US9706337W WO9738968A1 WO 1997038968 A1 WO1997038968 A1 WO 1997038968A1 US 9706337 W US9706337 W US 9706337W WO 9738968 A1 WO9738968 A1 WO 9738968A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
hydrocarbyl
amine
preparing
substituted
Prior art date
Application number
PCT/US1997/006337
Other languages
English (en)
Inventor
Jeffrey John Scheibel
Original Assignee
The Procter & Gamble Company
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 The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP9537347A priority Critical patent/JPH11507953A/ja
Priority to EP97920413A priority patent/EP0898560A1/fr
Priority to BR9708718A priority patent/BR9708718A/pt
Publication of WO1997038968A1 publication Critical patent/WO1997038968A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/12—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/50—Ethers of hydroxy amines of undetermined structure, e.g. obtained by reactions of epoxides with hydroxy amines
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/42—Amino alcohols or amino ethers
    • C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • C11D1/75—Amino oxides

Definitions

  • the present invention relates to processes for preparing substituted alkyl amines and surfactants therefrom.
  • laundry detergents and other cleaning compositions present a considerable challenge, since modern compositions are required to remove a variety of soils and stains from diverse substrates.
  • laundry detergents, hard surface cleaners, shampoos and other personal cleansing compositions, hand dishwashing detergents and detergent compositions suitable for use in automatic dishwashers, and the like all require the proper selection and combination of ingredients in order to function effectively.
  • such detergent compositions will contain one or more types of surfactants which are designed to loosen and remove soils and stains.
  • the removal of body soils, greasy/oily soils and certain food stains quickly and efficiently can be problematic. Indeed, while some surfactants and surfactant combinations exhibit optimal performance on certain types of soils and stains, they can actually diminish performance on other soils.
  • surfactants which remove greasy/oily soils from fabrics can sometimes be sub-optimal for removing particulate soils, such as clay.
  • particulate soils such as clay.
  • surfactants and surfactant combinations are available to the detergent manufacturer, the reality is that many such ingredients are specialty chemicals which are not suitable in low unit cost items such as home-use laundry detergents.
  • home-use products such as laundry detergents still mainly comprise one or more of the conventional ethoxylated nonionic and/or sulfated or sulfonated anionic surfactants, presumably due to economic considerations and the need to formulate compositions which function reasonably well with a variety of soils and stains and a variety of fabrics.
  • fatty tertiary amines are prepared from natural fatty acid feedstocks.
  • the present invention provides a commercial route to the use of synthetic alcohol feedstocks.
  • the present invention provides direct syntheses processes for substituted amines which involve the reaction of an alkyl sulfate with a mono-, or bis-alkoxy amine.
  • the processes have important commercial advantages in that they can be conducted in a water solvent at relatively modest temperatures and pressures.
  • the present invention encompasses a process (I) for preparing substituted tertiary amines ofthe formula:
  • R is C6-C22 hydrocarbyl (alkyl, alkenyl, linear or branched)
  • R' is C1-C22 hydrocarbyl
  • M is a water-solubilizing cation, especially sodium. Water or excess amine reactant can be used as the reaction solvent.
  • the invention also encompasses a process (II) for preparing substituted tertiary amines ofthe formula:
  • R is C6-C22 hydrocarbyl and M is a water- solubilizing cation.
  • M water- solubilizing cation.
  • the invention also encompasses a process (III) for preparing substituted tertiary amines ofthe formula:
  • the invention also encompasses a process for preparing ethoxylated tertiary amines ofthe formula:
  • the invention also encompasses a process for preparing ethoxylated tertiary amines of the formula:
  • the invention also encompasses processes for preparing cationic surfactants by quaternizing the tertiary amines prepared according to the above processes, (I), (II), (III) and (IV), respectively, and the ethoxylates thereof. This can be accomplished, for example, by reacting the ethoxylated tertiary amines with reactants R"Z, wherein R" is, for example C1-C5 (preferably methyl) hydrocarbyl, X-CH2CH2OH, and the like, wherein X is Cl, Br, methylsulfate, and the like.
  • R"Z reactants
  • the foregoing conventional steps (a)-(d) employ either high temperatures or multiple reactors or separation equipment or flammable metal catalysts such as Raney Ni (trademark), or use ammonia, or generate undesirable impurities, or limit the potential chain length flexibility, i. e., only natural oil based, all of which can result in processing complexity, high equipment costs and sub-optimal yields, with the net result of higher overall costs for the desired substituted amines.
  • Other conventional processes utilize fatty alkyl halides or fatty tertiary amines which can also produce undesirable impurities and by-products.
  • the present process directly converts alkyl sulfates into the desired substituted amines.
  • various steps of the present process can use water as the reaction solvent.
  • the sodium sulfate by-product remains in the water phase and helps "salt- out" the high purity substituted amine reaction product as a separate phase. Thus, recovery of the substituted amine reaction product is simple and inexpensive.
  • the sodium sulfate by-product can be recovered for use in the manufacture of detergent granules.
  • the present process can be conducted at relatively modest pressures, thereby avoiding the need for expensive, high pressure reactors. Although typically water is used, with sufficient excess amine reactant the water may not be necessary as amine can act as solvent and reactant.
  • reaction Process I for reaction Process I, hereinafter, the following parameters summarize the optional and preferred reaction conditions herein.
  • the reaction herein is preferably conducted in an aqueous medium.
  • Reaction temperatures are typically in the range of 100-230°C.
  • Reaction pressures are 50-1000 psig.
  • a base preferably sodium hydroxide, can be used to react with the HSO4- generated during the reaction, or an excess of the amine can be employed to also react with the acid.
  • the mole ratio of amine to alkyl sulfate is typically from 10:1 to 1:1.5; preferably from 5:1 to 1 :1.1 ; more preferably from 2:1 to 1:1.
  • the desired substituted amine is simply allowed to separate as a distinct phase from the aqueous reaction medium in which it is insoluble.
  • reaction mixture may be dried and added to the heavy duty granular detergent product since separation of the water and organic phase may not be possible with some chain length of alkylsulfates.
  • the process herein is preferably conducted using C12-C13 alkyl sulfate, sodium salt and N-methyl monoethanolamine.
  • reaction Process II hereinafter, the following parameters summarize the optional and preferred reaction conditions herein.
  • the reaction herein is preferably conducted in an aqueous medium. Reaction temperatures are typically in the range of 140-200°C. Reaction pressures are 50-1000 psig.
  • a base catalyst, preferably sodium hydroxide can be used.
  • the mole ratio of reactants are 2:1 to 1 :1 amine to alkyl sulfate.
  • the desired substituted amine is simply allowed to separate as a distinct phase from the aqueous reaction medium in which it is insoluble.
  • the process herein is preferably conducted using C12-C13 alkyl sulfate, sodium salt.
  • the reaction Process II results in products which are sufficiently soluble in the aqueous reaction medium that gels may form.
  • an alternate, two-step synthesis Process III hereinafter, may be more desirable in some commercial circumstances.
  • the first step in Process III is conducted as in Process I.
  • the second step is preferably conducted using ethylene oxide and an acid such as HCl which provides the quaternary surfactant.
  • HCl an acid
  • chlorohydrin i.e., chloroethanol
  • chloroethanol can also be reacted to give the desired bishydroxyethyl derivative.
  • Process IV is conducted using ethylene oxide under standard ethoxylation conditions, without catalyst, to achieve monoethoxylation as shown below.
  • EO represents the -CH2CH2O- unit.
  • Process I-III either an inorganic base or an organic base or excess amine reactant is used to neutralize generated HSO4.
  • PROCESS (ID R— OSO 3 " Na + + H-N— [(EO)H] 2 - ⁇ AL ⁇ .
  • Processes (I)-(IV) can be further ethoxylated using base catalyst and optionally quatted.
  • Process III gives a quaternary product of the bishydroxy material with a methyl group and Cl counterion.
  • the product of Process I can be ethoxylated under base catalyzed conditions to give R-N(CH3)(CH2CH2O) x -H which can be quatted with CH3C1 to give R-N(CH3)2(CH2CH2O) x -H+ Cl- or quatted with ethylene oxide and HCl to give new monoethoxylated monohydroxyethyl quaternary surfactants. While the above Processes (I), (II), (III) and (IV) are illustrated with reactants carrying the preferred EO units, propoxy, iso-propoxy, butoxy, and mixtures thereof, and mixtures with EO units, can also be used.
  • parent R- or R(EO)x-substituted mono- or bis-hydroxyethyl amine can be further alkoxylated (preferably ethoxylated using conventional ethylene oxide reactions. Following ethoxylation, the resulting amines can be quaternized using standard reactants and conditions.
  • the glass liner is sealed into 3 L, stainless steel, rocking autoclave, purged twice with 260 psig nitrogen and then heated to 160-180°C under 700-800 psig nitrogen for 3 hours. The mixture is cooled to room temperature and the liquid contents of the glass liner are poured into a 1 L separatory funnel. The mixture is separated into a clear lower layer, turbid middle layer and clear upper layer.
  • the clear upper layer is isolated and placed under full vacuum ( ⁇ 100 mm Hg) at 60-65°C with mixing to remove any residual water.
  • the clear liquid turns cloudy upon removing residual water as additional salts crystallizes out.
  • the liquid is vacuum filtered to remove salts to again obtain a clear, colorless liquid. After a few days at room temperature, additional salts crystallize and settle out.
  • the liquid is vacuum filtered to remove solids and again a clear, colorless liquid is obtained which remains stable.
  • the isolated clear, colorless liquid is the title product by NMR analysis and is >90% by GC analysis with a typical recovery of >90%.
  • Example II Preparation of N.N-Bis(2-hvdroxyethvDdodecylamine (Process II) To a glass autoclave liner is added 19.96 g of sodium dodecyl sulfate (0.06921 moles), 14.55 g of diethanolamine (0.1384 moles), 7.6 g of 50 wt. % sodium hydroxide solution (0.095 moles) and 72 g of distilled H2O. The glass liner is sealed into a 500 ml, stainless steel, rocking autoclave and heated to 160-180°C under 300-400 psig nitrogen for 3-4 hours.
  • the mixture is cooled to room temperature and the liquid contents of the glass liner are poured into a 250 ml separatory funnel along with 80 ml of chloroform.
  • the funnel is shaken well for a few minutes and then the mixture is allowed to separate.
  • the lower chloroform layer is drained and the chloroform evaporated off to obtain product.
  • Example III Preparation of N.N-Bis(2-hvdroxyemvDdodecylamine (Process III) 1 Mole of sodium dodecyl sulfate is reacted with 1 mole of ethanolamine in the presence of base in the manner described in Example (II). The resulting 2- hydroxyethyldodecylamine is recovered and reacted with 1-chloroethanol to prepare the title compound.
  • the glass liner is sealed into a 500 ml, stainless steel, rocking autoclave and heated to 160-180°C under 300-400 psig nitrogen for 3-4 hours. The mixture is cooled to room temperature and the liquid contents of the glass liner are poured into a 250 ml separatory funnel along with 80 ml of chloroform. The funnel is shaken well for a Tew minutes and then allowed mixture to separate. The lower chloroform layer is drained and the chloroform is evaporated off to obtain product. The product is then reacted with 1 molar equivalent of ethylene oxide in the absence of base catalyst at 120- 130°C to produce the desired final product.
  • Example VI Preparation of Dodecyl Dimethyl Pentaethylene glycol Ammonium Chloride
  • 100 g of N-(2-hydroxyethyl)-N- methyldodecylamine (0.4108 moles prepared according to process I) and 0.47 of sodium (0.0204 moles).
  • the reaction mixture is heated to 120-130°C and mixed under ethylene oxide atmosphere until 72.37 g (1.643 moles) of ethylene oxide has been absorbed.
  • the reaction is purged with nitrogen and 170 g of 2-propanol is added.
  • reaction mixture is added to glass autoclave liner, sealed liner in 3 L, stainless steel, rocking autoclave, purged once with 250 psig nitrogen, once with 50 psig methyl chloride and is charged to 65-70 psig with methyl chloride and heated to 75-80°C with mixing for 15 hours.
  • the reaction is cooled reaction to 50°C, removed from the autoclave and 2-propanol is evaporated off to obtain product.
  • Example VII Preparation of Bis(2-hvdroxyethyl > ) Dodecyl Methyl Ammonium Chloride To a 1 L round bottom flask equipped with magnetic stir bar, water cooled condenser and nitrogen line is added 200 g of N-(2-hydroxyethyl)-N- methyldodecyiamine (0.8216 moles prepared according to process I), 66.15 g of 2- chloroethanol (0.8216 moles) and 200 g of ethanol. The mixture is heated to reflux for 24 hours and then evaporated off ethanol to obtain product.
  • the reaction is purged with nitrogen.
  • the reaction mixture is ready for use as an aqueous stock solution of product.
  • the tertiary amines and/or alkoxylated tertiary amines can also be oxidized to form the corresponding amine oxide surfactants.

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

Abstract

On fait réagir des hydrocarbyl-sulfates avec des alcoxy-amines. Les amines substituées obtenues peuvent être éthoxylées, quaternarisées et/ou oxydées pour former des agents tensioactifs détergents.
PCT/US1997/006337 1996-04-18 1997-04-16 Synthese d'amines substituees WO1997038968A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP9537347A JPH11507953A (ja) 1996-04-18 1997-04-16 置換アミンの合成
EP97920413A EP0898560A1 (fr) 1996-04-18 1997-04-16 Synthese d'amines substituees
BR9708718A BR9708718A (pt) 1996-04-18 1997-04-16 Sínteses de aminas substituídas

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US1558496P 1996-04-18 1996-04-18
US60/015,584 1996-04-18

Publications (1)

Publication Number Publication Date
WO1997038968A1 true WO1997038968A1 (fr) 1997-10-23

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Family Applications (1)

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PCT/US1997/006337 WO1997038968A1 (fr) 1996-04-18 1997-04-16 Synthese d'amines substituees

Country Status (7)

Country Link
EP (1) EP0898560A1 (fr)
JP (2) JPH11507953A (fr)
CN (1) CN1321633A (fr)
AR (1) AR006700A1 (fr)
BR (1) BR9708718A (fr)
CA (1) CA2251847A1 (fr)
WO (1) WO1997038968A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6333433B1 (en) * 1998-11-09 2001-12-25 Council Of Scientific Industrial Research Process for synthesis of novel cationic amphiphiles containing N-hydroxyalkl group for intracellular delivery of biologically active molecules
FR2967899A1 (fr) * 2010-11-25 2012-06-01 Oreal Composition pour traiter les fibres keratiniques comprenant un compose cationique comprenant deux chaines grasses eventuellement hydroxylees
US8247482B2 (en) * 2007-11-20 2012-08-21 Perstorp France Hydrophilic polyisocyanate compositions based on phosphate esters
US9605163B2 (en) 2011-07-28 2017-03-28 Angus Chemical Company Aminoalcohol compounds and their use as zero or low VOC additives for paints and coatings

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6224627B2 (ja) * 2012-02-14 2017-11-01 ダウ グローバル テクノロジーズ エルエルシー 非イオン性界面活性剤組成物
CN106905171B (zh) * 2017-03-31 2018-12-11 浙江大学 2-[2-叔丁氧基乙氧基]-乙胺的制备方法

Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1923178A (en) * 1930-03-20 1933-08-22 Ig Farbenindustrie Ag Hydroxy alkyl ethers of tertiary amines and process of preparing same
DE837532C (de) * 1950-06-25 1952-04-28 Schuelke & Mayr Ag Verfahren zur Herstellung quartaerer Ammoniumverbindungen, die eine Carbonsaeureamidgruppe enthalten
US2597260A (en) * 1951-02-16 1952-05-20 Armour & Co Preparation of nu-aliphatic morpholines
GB1084134A (en) * 1964-07-14 1967-09-20 Mafchon Products Ltd Novel quaternary ammonium salts, their preparation and use as surface-active agents
GB1087414A (en) * 1963-06-25 1967-10-18 Marchon Products Ltd Improvements in or relating to amine oxides as surfaceactive agents
DE2646595A1 (de) * 1976-10-15 1978-04-20 Hoechst Ag Sinterfaehige feinteilige polyvinylchlorid-formmassen
EP0102140A1 (fr) * 1982-05-12 1984-03-07 The Procter & Gamble Company Préparation catalytique d'amines à partir de sulfates d'alkyle
JPS61209245A (ja) * 1985-03-14 1986-09-17 Denki Kagaku Kogyo Kk 熱可塑性樹脂組成物
US4650865A (en) * 1985-02-08 1987-03-17 Henkel Kommanditgesellschaft Auf Aktien Process for preparing tertiary ether amines
JPS6364701A (ja) * 1986-09-05 1988-03-23 花王株式会社 木材防腐剤
JPS63227643A (ja) * 1987-03-18 1988-09-21 Kao Corp 帯電防止性スチレン系樹脂組成物
DE3906096A1 (de) * 1989-02-27 1990-09-06 Henkel Kgaa Verfahren zur herstellung von etheraminsulfaten und ihre verwendung als schaumarme tenside
JPH05178731A (ja) * 1991-12-27 1993-07-20 New Japan Chem Co Ltd シャンプー組成物
EP0569904A2 (fr) * 1992-05-11 1993-11-18 ALBRIGHT & WILSON UK LIMITED Procédé pour la préparation de hydrates de carbone utilisés comme tensioactifs et leurs précurseurs
JPH06107524A (ja) * 1992-03-04 1994-04-19 New Japan Chem Co Ltd 毛髪処理剤組成物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3379763A (en) * 1964-09-01 1968-04-23 Armour & Co Preparation of primary and secondary amines from alkyl sulfates
US3378588A (en) * 1964-09-01 1968-04-16 Armour Ind Chem Co Preparation of tertiary amines from alkyl sulfates

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1923178A (en) * 1930-03-20 1933-08-22 Ig Farbenindustrie Ag Hydroxy alkyl ethers of tertiary amines and process of preparing same
DE837532C (de) * 1950-06-25 1952-04-28 Schuelke & Mayr Ag Verfahren zur Herstellung quartaerer Ammoniumverbindungen, die eine Carbonsaeureamidgruppe enthalten
US2597260A (en) * 1951-02-16 1952-05-20 Armour & Co Preparation of nu-aliphatic morpholines
GB1087414A (en) * 1963-06-25 1967-10-18 Marchon Products Ltd Improvements in or relating to amine oxides as surfaceactive agents
GB1084134A (en) * 1964-07-14 1967-09-20 Mafchon Products Ltd Novel quaternary ammonium salts, their preparation and use as surface-active agents
DE2646595A1 (de) * 1976-10-15 1978-04-20 Hoechst Ag Sinterfaehige feinteilige polyvinylchlorid-formmassen
EP0102140A1 (fr) * 1982-05-12 1984-03-07 The Procter & Gamble Company Préparation catalytique d'amines à partir de sulfates d'alkyle
US4650865A (en) * 1985-02-08 1987-03-17 Henkel Kommanditgesellschaft Auf Aktien Process for preparing tertiary ether amines
JPS61209245A (ja) * 1985-03-14 1986-09-17 Denki Kagaku Kogyo Kk 熱可塑性樹脂組成物
JPS6364701A (ja) * 1986-09-05 1988-03-23 花王株式会社 木材防腐剤
JPS63227643A (ja) * 1987-03-18 1988-09-21 Kao Corp 帯電防止性スチレン系樹脂組成物
DE3906096A1 (de) * 1989-02-27 1990-09-06 Henkel Kgaa Verfahren zur herstellung von etheraminsulfaten und ihre verwendung als schaumarme tenside
JPH05178731A (ja) * 1991-12-27 1993-07-20 New Japan Chem Co Ltd シャンプー組成物
JPH06107524A (ja) * 1992-03-04 1994-04-19 New Japan Chem Co Ltd 毛髪処理剤組成物
EP0569904A2 (fr) * 1992-05-11 1993-11-18 ALBRIGHT & WILSON UK LIMITED Procédé pour la préparation de hydrates de carbone utilisés comme tensioactifs et leurs précurseurs

Non-Patent Citations (16)

* Cited by examiner, † Cited by third party
Title
ABH. AKAD. WISS. DDR, ABT. MATH., NATURWISS., TECH. (1987), VOLUME DATE 1986, (1N), 589-94 *
ANTICANCER RES., vol. 8, no. 6, 1988, pages 1361 - 6 *
CHEM. ANAL. (WARSAW) (1981), 26(3), 469-75 *
CHEMICAL ABSTRACTS, vol. 101, no. 22, 26 November 1984, Columbus, Ohio, US; abstract no. 198626, IKEDA, ISAO ET AL: "Structural effects of the isomeric hydrophilic groups of surfactants on their properties. I. Monodisperse poly(oxyethylene) alkylamines" XP002035395 *
CHEMICAL ABSTRACTS, vol. 106, no. 10, 9 March 1987, Columbus, Ohio, US; abstract no. 68304, MAEDA, TETSUO: "Rubber-containing styrene polymer compositions" XP002035399 *
CHEMICAL ABSTRACTS, vol. 108, no. 11, 14 March 1988, Columbus, Ohio, US; abstract no. 94034, WEDLER, C. ET AL: "Preparation and some properties of amine oxides derived from defined ethylene oxide adducts" XP002035404 *
CHEMICAL ABSTRACTS, vol. 109, no. 15, 10 October 1988, Columbus, Ohio, US; abstract no. 124403, IWASAKI, TETSUHARU ET AL.: "Quaternary ammonium salt-containing wood preservatives" XP002035398 *
CHEMICAL ABSTRACTS, vol. 110, no. 14, 3 April 1989, Columbus, Ohio, US; abstract no. 116034, HORIBATAKE ET AL.: "Antistatic styrene resin composition" XP002035397 *
CHEMICAL ABSTRACTS, vol. 110, no. 19, 8 May 1989, Columbus, Ohio, US; abstract no. 165558, S. C. CRUMPTON ET AL.: "Novel lipid analogs with cytostatic and cytocidal activity" XP002035400 *
CHEMICAL ABSTRACTS, vol. 111, no. 10, 4 September 1989, Columbus, Ohio, US; abstract no. 86206, SZCZEPANIAK, STANISLAW ET AL: "Bath for electrodeposition of tin and tin-cadmium coatings" XP002035403 *
CHEMICAL ABSTRACTS, vol. 115, no. 12, 23 September 1991, Columbus, Ohio, US; abstract no. 118389, SZCZEPANIAK, STANISLAW: "Quaternary ammonium salt-containing pickling bath for precision steel parts" XP002035402 *
CHEMICAL ABSTRACTS, vol. 120, no. 2, 10 January 1994, Columbus, Ohio, US; abstract no. 14633, AOYANAGI, KENJI ET AL: "Shampoos containing hair-conditioning surfactants" XP002035405 *
CHEMICAL ABSTRACTS, vol. 121, no. 12, 19 September 1994, Columbus, Ohio, US; abstract no. 141214, AOYANAGI, KENJI ET AL: "Hair preparations containing cationic surfactants" XP002035401 *
CHEMICAL ABSTRACTS, vol. 97, no. 12, 20 September 1982, Columbus, Ohio, US; abstract no. 103650, SZYMANOWSKI, JAN ET AL: "Analysis of the content of the positional isomers of oxyethylated hexylamines by gas chromatography-mass spectrometry" XP002035396 *
KUO, P. L. ET AL: "Long chain N-alkyl monoaza crown ethers", J. AM. OIL CHEM. SOC. (1980), 57(7), 227-9, XP002035394 *
TENSIDE DETERG. (1984), 21(5), 252-4 *

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US6333433B1 (en) * 1998-11-09 2001-12-25 Council Of Scientific Industrial Research Process for synthesis of novel cationic amphiphiles containing N-hydroxyalkl group for intracellular delivery of biologically active molecules
US6541649B2 (en) 1998-11-09 2003-04-01 Council Of Scientific & Industrial Research Process for synthesis of novel cationic amphiphiles containing N-hydroxyalkyl group for intracellular delivery of biologically active molecules
US8247482B2 (en) * 2007-11-20 2012-08-21 Perstorp France Hydrophilic polyisocyanate compositions based on phosphate esters
FR2967899A1 (fr) * 2010-11-25 2012-06-01 Oreal Composition pour traiter les fibres keratiniques comprenant un compose cationique comprenant deux chaines grasses eventuellement hydroxylees
US9605163B2 (en) 2011-07-28 2017-03-28 Angus Chemical Company Aminoalcohol compounds and their use as zero or low VOC additives for paints and coatings

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EP0898560A1 (fr) 1999-03-03
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CA2251847A1 (fr) 1997-10-23
BR9708718A (pt) 1999-08-03
JPH11507953A (ja) 1999-07-13
CN1321633A (zh) 2001-11-14

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