EP0022562B1 - Quaternäre Ammoniumverbindungen, deren Herstellung und deren Verwendung als Wäscheweichspülmittel - Google Patents

Quaternäre Ammoniumverbindungen, deren Herstellung und deren Verwendung als Wäscheweichspülmittel Download PDF

Info

Publication number
EP0022562B1
EP0022562B1 EP80103954A EP80103954A EP0022562B1 EP 0022562 B1 EP0022562 B1 EP 0022562B1 EP 80103954 A EP80103954 A EP 80103954A EP 80103954 A EP80103954 A EP 80103954A EP 0022562 B1 EP0022562 B1 EP 0022562B1
Authority
EP
European Patent Office
Prior art keywords
formula
compounds
alkyl
alkenyl
methyl
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.)
Expired
Application number
EP80103954A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0022562A3 (en
EP0022562A2 (de
Inventor
Erich Dr. Hoffmann
Wolfgang Dr. Wagemann
Günther Dr. Täuber
Adolf Dr. May
Hans-Walter Dr. Bücking
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.)
Hoechst AG
Original Assignee
Hoechst AG
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=6075796&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0022562(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to AT80103954T priority Critical patent/ATE13879T1/de
Publication of EP0022562A2 publication Critical patent/EP0022562A2/de
Publication of EP0022562A3 publication Critical patent/EP0022562A3/de
Application granted granted Critical
Publication of EP0022562B1 publication Critical patent/EP0022562B1/de
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • 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

Definitions

  • DE-A-1 935499 already discloses the use of N, N-di-ethanolamides esterified with fatty acids as softeners. Similar structured connections are known from DE-B-2 430140 as finishing agents for textiles, paper and hair. In contrast, novel quaternary ammonium compounds have now been found which are suitable as fabric softeners. From DE-A-2 025 944 quaternary ammonium compounds are already known as fabric softeners which contain a long-chain alkyl radical, usually two low molecular weight alkyl radicals and an acyloxy radical bonded via a hydroxy-1,3-propylene group on the quaternary nitrogen atom. However, these compounds have a lower softening effect than the compounds described below.
  • the invention relates to quaternary ammonium compounds of the formula 1 wherein R 1 is alkyl, 2-hydroxyalkyl or alkenyl each having 8 to 30 C atoms, R 2 C 1 ⁇ C 4 alkyl, or benzyl, A is a group of the formulas B has the same meaning as A and additionally a C 1 -C 4 alkylene group, R Cs-C3o-alkyl or Cs-Cso-alkenyl, X and Y are hydrogen or methyl, where X and Y are not methyl at the same time, m 1 or 2, n is a number from 1 to 20 and A e is an anion.
  • Preferred compounds of the formula 1 are those in which R 1 is alkyl, 2-hydroxyalkyl or alkenyl each having 14-24 carbon atoms, R 2 is methyl, RC 14 -C 24 alkyl or C 14 -C 24 alkenyl, n is a number from 1 to 5, A e represents a halogen, methosulfate or methophosphate ion and A, B, X, Y and m have the abovementioned meaning.
  • R 1 is C 16 -C 18 alkyl or C 16 -C 18 alkenyl
  • R 2 is methyl
  • a and B a group of the formula and A e represents a chloride or methosulfate ion.
  • the reaction in the first stage is preferably carried out with the free fatty acid in the absence of solvents and at temperatures of approximately 130 to 180 ° C., preferably 150 to 170 ° C.
  • an acidic catalyst such as p-toluenesulfonic acid.
  • the molar ratio of the fatty acid of formula 3 to the aminoxalkylate of formula 2 is 0.7 to 1.1, preferably 0.7 to 0.9 mol of fatty acid per 1 mol of aminoxalkylate.
  • the intermediate product of formula 4 thus obtained is then dissolved in an alcohol or dispersed in water and quaternized with a compound of the above formulas in a conventional manner at temperatures below 100 ° C., preferably at 40-80 ° C.
  • This reaction can also be carried out in the absence of a solvent.
  • concentrates containing about 20 to 35% by weight of the compound of the formula 1 are obtained.
  • the compounds of the formula 1 can be obtained in pure form by distilling off the water or solvent. However, the concentrates can be diluted directly also for further use to a level of about 1 to 30, preferably 4 to 10 parts by weight 0 / o.
  • the compounds of formula 2 serving as starting products are known as such. They are obtained by oxyalkylating fatty alkyl amines or by reacting fatty amines with 2,3-epoxypropanol.
  • suitable fatty alkylamines are dodecyl-, myristyl-, cetyl-, oleyl-, behenyl- or preferably stearylamine or mixtures of such fatty alkylamines which are derived from naturally occurring fats such as coconut oil or tallow.
  • the compounds of formula 1 according to the invention are suitable as fabric softeners and are in the form of aqueous dispersions with an active substance content of 1 to 15 wt .-%, usually 4-10 wt 0 / o, of the compounds of formula 1 following the washing of the Put textile material in the last rinsing bath. The textile material is then dried.
  • These fabric softeners can also contain other substances and auxiliaries that are commonly used in fabric softeners. These include e.g. B. cationic or nonionic surface-active substances, electrolytes, acidifying agents, organic complexing agents, optical brighteners or solubilizers, and colorants and fragrances.
  • the products are used to additionally influence the handle of the goods or other properties of the textiles to be treated or to adjust the viscosity, regulate the pH or increase the cold stability of the solutions.
  • the compounds according to the invention give any textile materials, especially those made of natural or regenerated cellulose, wool, cellulose acetate, triacetate, polyamide, polyacrylonitrile, polyester, polypropylene, a pleasant and soft feel.
  • Use as a laundry treatment agent for terry towels and underwear is particularly advantageous.
  • 171.5 g of the compound of the formula are placed in a 500 ml flask equipped with a stirrer, nitrogen inlet, contact thermometer and descending condenser 104 g of stearic acid, 2 g of hydrazine hydrate and 2 g of p-toluenesulfonic acid are introduced under nitrogen and slowly heated to 150.degree. After an hour, the temperature is raised to 175 ° C and maintained until the acid number is less than 6. The water of reaction released is continuously distilled off. Then allowed to cool to 70 ° C, mixed with about 112 ml of warm water and transferred to the 70 ° C warm mixture in a 1 liter autoclave.
  • Example 2 In an apparatus as in Example 1, 184 g of di- (2,3-dihydroxypropyl) stearylamine and 100 g of stearic acid (molar ratio of aminoxalkylate to stearic acid 0.89) are reacted as described in Example 1. After 7 h at 175 ° C., 270 g of monoesters with an acid number of 5 are obtained. About 30% by weight of warm water is added and the 70 ° C warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, methyl chloride is pressed in gaseously from a bomb at 70-80 ° C until a constant pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. 400 g of a mass which is waxy at room temperature and has a solids content of 75% are obtained.
  • Example 2 In an apparatus as in Example 1, 176 g of di-2-hydroxyethyl- (2-hydroxypentadecyl / octadecyl) amine and 117 g of stearic acid (molar ratio of aminoxethylate to stearic acid 1: 0.91) are reacted as described. After 7 h at 175 ° C., 279 g of condensation product with an acid number of 6 are obtained. 30 percent by weight of warm water are added and the 70 ° C. warm mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, methyl chloride is pressed in from a bomb at 70 ⁇ 80 ° C until a constant pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. 420 g of a mass which is waxy at room temperature and has a solids content of 72% are obtained.
  • Example 2 In an apparatus as in Example 1, 156 g of methyl (2,3-dihydroxypropyl) stearylamine and 91 g of stearic acid (molar ratio of aminoxalkylate to stearic acid 1: 0.88) are reacted as described. After 7 h at 175 ° C. 225 g of ester with an acid number of 6 are obtained. 30% by weight of warm water are stirred in and the 70 ° C. mixture is transferred to a 1 liter autoclave. After flushing with nitrogen, methyl chloride is pressed in gaseously from a bomb at 70-80 ° C until a constant pressure of 5 bar is reached. The mixture is stirred at 60 ° C for two hours and relaxed carefully. 360 g of a mass which is waxy at room temperature and has a solids content of 71% are obtained.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
EP80103954A 1979-07-14 1980-07-10 Quaternäre Ammoniumverbindungen, deren Herstellung und deren Verwendung als Wäscheweichspülmittel Expired EP0022562B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT80103954T ATE13879T1 (de) 1979-07-14 1980-07-10 Quaternaere ammoniumverbindungen, deren herstellung und deren verwendung als waescheweichspuelmittel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19792928603 DE2928603A1 (de) 1979-07-14 1979-07-14 Quaternaere ammoniumverbindungen, deren herstellung und deren verwendung als waescheweichspuelmittel
DE2928603 1979-07-14

Publications (3)

Publication Number Publication Date
EP0022562A2 EP0022562A2 (de) 1981-01-21
EP0022562A3 EP0022562A3 (en) 1981-10-21
EP0022562B1 true EP0022562B1 (de) 1985-06-19

Family

ID=6075796

Family Applications (1)

Application Number Title Priority Date Filing Date
EP80103954A Expired EP0022562B1 (de) 1979-07-14 1980-07-10 Quaternäre Ammoniumverbindungen, deren Herstellung und deren Verwendung als Wäscheweichspülmittel

Country Status (8)

Country Link
US (1) US4339391A (ja)
EP (1) EP0022562B1 (ja)
JP (1) JPS5618946A (ja)
AR (1) AR221651A1 (ja)
AT (1) ATE13879T1 (ja)
BR (1) BR8004336A (ja)
CA (1) CA1167054A (ja)
DE (2) DE2928603A1 (ja)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3127239A1 (de) * 1981-07-10 1983-01-20 Hoechst Ag, 6000 Frankfurt Quartaere n-alkyl-n,n',n'-polyoxyalkyl-(alpha),(omega)-diaminoalkylenfettsaeureester, verfahren zu deren herstellung und deren verwendung
GB8414944D0 (en) * 1984-06-12 1984-07-18 Ici Plc Fabric conditioners
DE3608455A1 (de) * 1986-03-14 1987-09-17 Nattermann A & Cie Phospholipidhaltige produkte, deren herstellung und verwendung
GB2188653A (en) * 1986-04-02 1987-10-07 Procter & Gamble Biodegradable fabric softeners
DE3623215A1 (de) * 1986-07-10 1988-01-21 Henkel Kgaa Neue quartaere ammoniumverbindungen und deren verwendung
DE3638918A1 (de) * 1986-11-14 1988-05-26 Henkel Kgaa Quartaere ammoniumverbindungen, deren herstellung und verwendung als textilnachbehandlungsmittel
DE3710064A1 (de) * 1987-03-27 1988-10-06 Hoechst Ag Verfahren zur herstellung von quaternaeren esteraminen und ihre verwendung
EP0293955B1 (en) 1987-05-01 1993-01-13 The Procter & Gamble Company Quaternary isopropyl ester ammonium compounds as fiber and fabric treatment compositions
US4808321A (en) * 1987-05-01 1989-02-28 The Procter & Gamble Company Mono-esters as fiber and fabric treatment compositions
JPH0742649B2 (ja) * 1987-05-26 1995-05-10 花王株式会社 柔軟仕上剤
US4789491A (en) * 1987-08-07 1988-12-06 The Procter & Gamble Company Method for preparing biodegradable fabric softening compositions
EP0309052B1 (en) * 1987-09-23 1992-11-25 The Procter & Gamble Company Stable biodegradable fabric softening compositions containing linear alkoxylated alcohols
US4840738A (en) * 1988-02-25 1989-06-20 The Procter & Gamble Company Stable biodegradable fabric softening compositions containing 2-hydroxypropyl monoester quaternized ammonium salts
US4954635A (en) * 1989-09-06 1990-09-04 The Procter & Gamble Company Process for preparing quaternized imidazoline fabric conditioning compounds
US5128473A (en) * 1991-02-01 1992-07-07 Sherex Chemical Company, Inc. Nitrogen-heterocyclic compounds and quaternary salts thereof
US5128053A (en) * 1991-02-06 1992-07-07 Sherex Chemical Company, Inc. Composition and process for treating fabrics in clothes dryers
US5182033A (en) * 1991-06-14 1993-01-26 Sherex Chemical Company, Inc. Polyamide salts
US5734069A (en) * 1992-08-05 1998-03-31 Sherex Chemical Co., Inc. Biodegradable amidoaminoesters
US5670472A (en) * 1994-04-19 1997-09-23 Witco Corporation Biodegradable ester diquaternary compounds and compositions containing them
US5523433A (en) * 1994-09-29 1996-06-04 Witco Corporation Process for the preparation of diethyl ester dimethyl ammonium chloride
US5525261A (en) * 1994-10-18 1996-06-11 Henkel Corporation Anti-static composition and method of making the same
US5916863A (en) * 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
US6271298B1 (en) 1999-04-28 2001-08-07 Southern Clay Products, Inc. Process for treating smectite clays to facilitate exfoliation
US6787592B1 (en) 1999-10-21 2004-09-07 Southern Clay Products, Inc. Organoclay compositions prepared from ester quats and composites based on the compositions
US6849680B2 (en) 2001-03-02 2005-02-01 Southern Clay Products, Inc. Preparation of polymer nanocomposites by dispersion destabilization
US7405187B2 (en) 2006-06-01 2008-07-29 The Procter & Gamble Company Concentrated perfume compositions
US20090163402A1 (en) * 2007-12-19 2009-06-25 Eastman Chemical Company Fabric softener
US20140050687A1 (en) 2011-04-28 2014-02-20 Estman Chemical Company Betaine esters and process for making and using
US20130177951A1 (en) * 2012-01-06 2013-07-11 Eastman Chemical Company Chemo-enzymatic process for preparing quaternary ammonium esters
CN111051485A (zh) 2017-09-06 2020-04-21 赢创运营有限公司 特别用于生产织物柔软剂配制物的包含季铵化合物的微乳剂
US11312926B2 (en) 2017-09-25 2022-04-26 Evonik Operations Gmbh Polysiloxane-containing concentrates with improved storage stability and use thereof in textile care compositions
BR112020026982A2 (pt) 2018-07-05 2021-03-30 Evonik Operations Gmbh Composições ativas para as formulações de lavanderia e de limpeza altamente viscosas
EP3590493A1 (de) 2018-07-05 2020-01-08 Evonik Operations GmbH Hybrid quats zur haarpflege

Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2189397A (en) * 1938-02-11 1940-02-06 Benjamin R Harris Organic nitrogenous base derivatives of ether derivatives
US2359043A (en) * 1939-07-07 1944-09-26 Firm Sandoz Ltd Softening textiles
US2712025A (en) * 1951-09-26 1955-06-28 Chessie E Rehberg Production of dicarboxylic acid esters of alpha-hydroxycarboxylic acid esters
US2775604A (en) * 1953-02-09 1956-12-25 Atlas Powder Co Quaternary ammonium halides
US3272712A (en) * 1962-10-29 1966-09-13 Oreal Quaternary ammonium salts of esters of fatty acids and a precursor of amino-2-hydroxy propanol, methods of their preparation and their use
US3342840A (en) * 1964-03-23 1967-09-19 Shell Oil Co Cationic ester production
FR2054337A5 (en) * 1969-07-12 1971-04-16 Basf Ag Finishing agents for textiles
US3661784A (en) * 1969-08-04 1972-05-09 Petrolite Corp Method of protecting metal surfaces against abrasive wear in submersible pumps
GB1287199A (en) * 1969-01-25 1972-08-31 Basf Ag New quaternary ammonium salts and their use in softening textile fibrous material
GB1296351A (ja) * 1968-06-25 1972-11-15
GB1296352A (ja) * 1968-06-25 1972-11-15
GB1374419A (en) * 1970-12-14 1974-11-20 Unilever Ltd Liquid washing compositions
GB1380705A (en) * 1970-12-23 1975-01-15 Kao Corp Textile treating composition
US3872138A (en) * 1971-11-09 1975-03-18 Kao Corp Process for the preparation of quaternary ammonium salts
DE2728841A1 (de) * 1976-07-02 1978-01-05 Unilever Nv Neue quaternaere ammoniumsalze, verfahren zu ihrer herstellung und diese enthaltende mittel
US4069309A (en) * 1972-09-19 1978-01-17 Avon Products, Inc. Cationic skin substantive sunscreen composition and method
US4128485A (en) * 1976-08-16 1978-12-05 Colgate-Palmolive Company Fabric softening compounds
EP0002857A1 (en) * 1977-12-23 1979-07-11 THE PROCTER & GAMBLE COMPANY Laundry detergent substrate articles

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2390942A (en) * 1941-10-13 1945-12-11 Emulsol Corp Ethers of alcohol amines
DE845520C (de) * 1949-06-22 1952-07-31 Schuelke & Mayr Aktien Ges Verfahren zur Herstellung quaternaerer Ammoniumverbindungen
NL285002A (ja) * 1961-11-02
BE745814A (fr) * 1969-04-30 1970-08-11 Henkel & Cie Gmbh Detergent contenant des assouplissants pour textiles
DE2025944A1 (en) * 1970-05-27 1971-12-09 Henkel & Cie GmbH, 4000 Dusseldorf Detergent compsns for textiles - with combined cleaning - and softening actions,contng quaternary ammonium salts of unsatd carb
DE2430140C3 (de) * 1974-06-24 1979-10-04 Rewo Chemische Werke Gmbh, 6497 Steinau Kationaktive Bis-(2-Acyloxypropyl)ammonium-Salze, Verfahren zu deren Herstellung und Mittel auf deren Basis

Patent Citations (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2189397A (en) * 1938-02-11 1940-02-06 Benjamin R Harris Organic nitrogenous base derivatives of ether derivatives
US2359043A (en) * 1939-07-07 1944-09-26 Firm Sandoz Ltd Softening textiles
US2712025A (en) * 1951-09-26 1955-06-28 Chessie E Rehberg Production of dicarboxylic acid esters of alpha-hydroxycarboxylic acid esters
US2775604A (en) * 1953-02-09 1956-12-25 Atlas Powder Co Quaternary ammonium halides
US3272712A (en) * 1962-10-29 1966-09-13 Oreal Quaternary ammonium salts of esters of fatty acids and a precursor of amino-2-hydroxy propanol, methods of their preparation and their use
US3342840A (en) * 1964-03-23 1967-09-19 Shell Oil Co Cationic ester production
GB1296352A (ja) * 1968-06-25 1972-11-15
GB1296351A (ja) * 1968-06-25 1972-11-15
GB1287199A (en) * 1969-01-25 1972-08-31 Basf Ag New quaternary ammonium salts and their use in softening textile fibrous material
FR2054337A5 (en) * 1969-07-12 1971-04-16 Basf Ag Finishing agents for textiles
US3661784A (en) * 1969-08-04 1972-05-09 Petrolite Corp Method of protecting metal surfaces against abrasive wear in submersible pumps
GB1374419A (en) * 1970-12-14 1974-11-20 Unilever Ltd Liquid washing compositions
GB1380705A (en) * 1970-12-23 1975-01-15 Kao Corp Textile treating composition
US3872138A (en) * 1971-11-09 1975-03-18 Kao Corp Process for the preparation of quaternary ammonium salts
US4069309A (en) * 1972-09-19 1978-01-17 Avon Products, Inc. Cationic skin substantive sunscreen composition and method
DE2728841A1 (de) * 1976-07-02 1978-01-05 Unilever Nv Neue quaternaere ammoniumsalze, verfahren zu ihrer herstellung und diese enthaltende mittel
US4137180A (en) * 1976-07-02 1979-01-30 Lever Brothers Company Fabric treatment materials
US4128485A (en) * 1976-08-16 1978-12-05 Colgate-Palmolive Company Fabric softening compounds
EP0002857A1 (en) * 1977-12-23 1979-07-11 THE PROCTER & GAMBLE COMPANY Laundry detergent substrate articles

Also Published As

Publication number Publication date
EP0022562A3 (en) 1981-10-21
ATE13879T1 (de) 1985-07-15
US4339391A (en) 1982-07-13
EP0022562A2 (de) 1981-01-21
BR8004336A (pt) 1981-02-03
CA1167054A (en) 1984-05-08
DE3070775D1 (en) 1985-07-25
DE2928603A1 (de) 1981-02-05
JPS5618946A (en) 1981-02-23
JPH0231060B2 (ja) 1990-07-11
AR221651A1 (es) 1981-02-27

Similar Documents

Publication Publication Date Title
EP0022562B1 (de) Quaternäre Ammoniumverbindungen, deren Herstellung und deren Verwendung als Wäscheweichspülmittel
DE2728841C2 (ja)
EP0082456B1 (de) Konzentrierte Vormischungen von Wäscheweichspülmitteln
EP0075168B1 (de) Ammoniumverbindungen
DE2631419A1 (de) Zusammensetzungen fuer die textilbehandlung
EP1194434A1 (de) Antimikrobielle siloxanquat-formulierungen, deren herstellung und verwendung
DE2730302A1 (de) Borsaeure-amin-umsetzungsprodukte, ihre herstellung und verwendung
DE2210087B2 (de) Imidazoliniumsalze und diese enthaltende Textüweichmachungsmittel
DE1445403A1 (de) Neue Sulfobetaine
EP0074057A2 (de) Perfluoralkylester, Verfahren zu deren Herstellung und ihre Verwendung als schmutzabweisendes Mittel
DE3638918A1 (de) Quartaere ammoniumverbindungen, deren herstellung und verwendung als textilnachbehandlungsmittel
EP0498050A2 (de) Fettsäureester des N-Methyl-N,N,N,-trihydroxyethyl-ammonium-methylsulfat enthaltende wässrige Emulsionen
US4118324A (en) Fabric softeners
DE2625945A1 (de) Neue quartaere ammoniumverbindungen und deren verwendung als textilweichmacher
EP0001620B1 (de) Quaternierte Amin-Amid Kondensationsprodukte und deren Verwendung in ölhaltigen Faserpräparationsmitteln
EP0011130A1 (de) Neue aliphatische Aminoether-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Textilweichmacher
EP0075065B1 (de) Verfahren zur Herstellung von quartären Ammoniumverbindungen
DE2930849A1 (de) Neue n-hydroxyalkylimidazolinderivate, deren herstellung und verwendung
EP0069948B1 (de) Quartäre N-Alkyl-N,N',N'-Polyoxyalkyl-alpha-omega-diaminoalkylenfettsäureester, Verfahren zu deren Herstellung und deren Verwendung
DE2936121A1 (de) Quaternaere ester von hydroxialkylamidoaminen, verfahren zu deren herstellung und deren verwendung als waescheweichspuelmittel
EP0023333A1 (de) Wäscheweichspülmittel
DE3730444A1 (de) Weichspuelmittel
EP0021431B1 (de) Quaternäre Alkylamino-di-alkylcarbonsäure-di-ester, Verfahren zu deren Herstellung und deren Verwendung
DE3816200C2 (de) Neue kationische oberflächenaktive Mittel vom quaternären Ammonium-Typ, Verfahren zu deren Herstellung und deren Verwendung, insbesondere zur Behandlung von Textilien und Zellulosematerialien
DE2539349A1 (de) Waeschenachbehandlungsmittel

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): AT BE CH DE FR GB IT NL SE

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Designated state(s): AT BE CH DE FR GB IT NL SE

17P Request for examination filed

Effective date: 19820218

ITF It: translation for a ep patent filed

Owner name: ING. C. GREGORJ S.P.A.

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): AT BE CH DE FR GB IT LI NL SE

REF Corresponds to:

Ref document number: 13879

Country of ref document: AT

Date of ref document: 19850715

Kind code of ref document: T

REF Corresponds to:

Ref document number: 3070775

Country of ref document: DE

Date of ref document: 19850725

ET Fr: translation filed
PLBI Opposition filed

Free format text: ORIGINAL CODE: 0009260

26 Opposition filed

Opponent name: AKZO N.V.

Effective date: 19860314

Opponent name: IMPERIAL CHEMICAL INDUSTRIES PLC

Effective date: 19860315

NLR1 Nl: opposition has been filed with the epo

Opponent name: AKZO N.V.

Opponent name: IMPERIAL CHEMICAL INDUSTRIES PLC

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 19860626

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19870731

Year of fee payment: 8

PLAB Opposition data, opponent's data or that of the opponent's representative modified

Free format text: ORIGINAL CODE: 0009299OPPO

R26 Opposition filed (corrected)

Opponent name: IMPERIAL CHEMICAL INDUSTRIES PLC * 860314 AKZO N.V

Effective date: 19860315

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

RDAG Patent revoked

Free format text: ORIGINAL CODE: 0009271

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: PATENT REVOKED

27W Patent revoked

Effective date: 19890422

GBPR Gb: patent revoked under art. 102 of the ep convention designating the uk as contracting state
NLR2 Nl: decision of opposition
BERE Be: lapsed

Owner name: HOECHST A.G.

Effective date: 19890731

EUG Se: european patent has lapsed

Ref document number: 80103954.6

PLAB Opposition data, opponent's data or that of the opponent's representative modified

Free format text: ORIGINAL CODE: 0009299OPPO