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
  • C11D3/39—Organic or inorganic per-compounds
  • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
  • C11D3/3905—Bleach activators or bleach catalysts
  • C11D3/3907—Organic compounds
  • C11D3/3917—Nitrogen-containing compounds

Definitions

• Inorganic persalts have long been known as bleach additives in detergents. However, since they only develop their optimal bleaching power at temperatures above 60 ° C, a number of organic compounds have been described for their activation which react with hydrogen peroxide to release a peroxycarboxylic acid during the washing process. This already has a bleaching and disinfecting effect at 40-60 ° C.
• activators such as N-acyl compounds (tetraacetylethylenediamine (TAED), tetraacetylmethylene diamine, tetraacetylglycoluril (TAGU)) or activated esters (pentaacetylglucose (PAG), acetoxybenzenesulfonate sodium, nonanoyloxibenzol sulfonate sodium (NOB) sulfonate sodium (NOB) sulfonate (S) given for example in US 4,248,928
• These activators in particular TAED, TAGU, PAG and NOBS
• TAED tetraacetylethylenediamine
• TAGU tetraacetylmethylene diamine
• TAGU tetraacetylglycoluril
• activated esters penentaacetylglucose (PAG), acetoxybenzenesulfonate sodium, nonanoyloxi
• Liquid textile detergents are being used more and more recently.
• a disadvantage of the heavy duty liquids available so far, however, is the lack of a bleaching system for removing stubborn, oxidizable stains.
• a number of patent applications therefore use aqueous bleaching systems based on hydrogen peroxide / activator Proposed that are stored at pH values ⁇ 7 and are only combined with the surfactant mixture before the start of washing, since this is the only way to ensure good storage stability.
• DE-351151, EP-217454, EP-225654 describe anhydrous, liquid heavy-duty detergents which, in addition to a surfactant mixture, auxiliaries and builders, also contain a bleaching system of the activator / persalt type. Dispersions of finely ground perborate monohydrate and TAED are claimed.
• the documents DE-3728256, DE-3,729,074 and EP 125,781 indicate the advantages of incorporating liquid, organic activators (e.g. acylals and diacetylmethylamine). However, the claimed activators (e.g.
• ethylidene acetate benzoate have the disadvantage that they are only soluble in water to a limited extent, can only be used as a suspension in water-containing formulations and dissolve only slowly during the bleaching process.
• Another disadvantage is that decomposition products form after perhydrolysis (low molecular weight aldehydes, N-methylacetamide). must be regarded as environmentally problematic.
• liquid activators e.g. DE-OS 27 33 849 also describes triacetylethanolamine, which is adsorbed on inorganic carrier materials, in powder detergents.
• triacylated ethanolamines are very readily miscible with water and, in the presence of hydrogen peroxide or other per compounds, release one mole of a peracid at room temperature.
• the invention therefore relates to the use of triacylated ethanolamine of the general formula (RCO) (R1CO) N- (CH2) 2-O-COR2 where R, R1, R2 are the same or different and are alkyl, alkenyl or aryl groups and the sum of all C atoms in the molecule is 8 to 14, as liquid, water-miscible peroxide activators in liquid detergents and cleaning agents.
• RCO triacylated ethanolamine of the general formula (RCO) (R1CO) N- (CH2) 2-O-COR2
• R, R1, R2 are the same or different and are alkyl, alkenyl or aryl groups and the sum of all C atoms in the molecule is 8 to 14, as liquid, water-miscible peroxide activators in liquid detergents and cleaning agents.
• Triacylated ethanolamines are compounds known per se, the textile finishing effect of which is known (US Pat. No. 2,143,765). To produce them, ethanolamine is reacted with an excess of a carboxylic acid anhydride or carboxylic acid halide at elevated temperature. For economic and ecological reasons, however, they are preferably produced using the two-stage process described below.
• ethanolamine is reacted with an acid at temperatures between 120 and 200 ° C with the release of water of reaction to the carboxylic acid monoethanolamide or N, O-diacylethanolamine.
• the product is reacted with a carboxylic anhydride at 130 to 170 ° C. in a second reaction step without further purification, the carboxylic acid formed being distilled off.
• the reaction can optionally in the presence of an acidic or basic catalyst such as sulfuric acid, p-toluenesulfonic acid or Sodium acetate and be carried out under reduced pressure.
• the carboxylic acid formed in the second reaction step can be introduced into the first reaction step, so that continuous production is possible.
• the water solubility of the acylation products obtained in this way is strongly dependent on the number of carbon atoms contained.
• Preferred compounds are triacetylethanolamine, diacetylpropionylethanolamine, tripropionylethanolamine, and benzoyldiacetylethanolamine, of which triacetylethanolamine has the best water solubility and is miscible with water in any ratio.
• Compounds with more than 14 carbon atoms show no advantage over known solid activators, since they have to be emulsified or dispersed because of insufficient solubility.
• Triacetylethanolamine (TAEA) in aqueous solution easily reacts with hydrogen peroxide or inorganic persalts to form peracetic acid, a highly bleaching and disinfecting substance.
• Perborates, percarbonates, persulfates or perphosphates in the form of their sodium or potassium salts can be used as inorganic persalts.
• the molar ratio of persalt: activator is 0.5-10 to 1, preferably 1-4 to 1.
• a stable bleaching mixture is obtained which can be used directly or in combination with other additives as a detergent, cleaning agent or disinfectant.
• the mixture may contain anionic or cationic surfactants, enzymes, peroxide stabilizers, antigelling agents, perfume and dyes as further constituents.
• a combination with others Peroxide activators or peroxy carboxylic acids such as dodecane diperoxy carboxylic acid are possible.
• Another area of application of the compounds described is the use as a peroxide activator in a powdered detergent. For this purpose, the liquid activator on a solid such. B. zeolite or sodium perborate and possibly stabilized by additional granulation or coating.
• the present invention is based on the property now found that the triacylated ethanolamines described are completely miscible with water. Due to this property, a completely homogeneous distribution of the peroxide activator in liquid detergents and in particular in the wash liquor is provided and the disadvantages resulting from the inhomogeneous distribution of solid peroxide activators in such detergents, such as the formation of bleaching spots, are avoided.
• TAEA releases a mole of peracetic acid very quickly, similar to pre-dissolved TAED. These perhydrolyses are faster than the formation of perisononanoic acid from isonobs.
• the tests were carried out in the Launder-O-Meter at 60 ° C using the test fabric WFK 10 G cotton (tea soiling) and EMPA cotton No. 114 (red wine soiling) in 15dH water.
• the bleaching systems (activator / perborate) were dosed so that 25 mg of active oxygen per liter of wash liquor resulted.
• 1.5 g of IEC basic washing powder per liter of washing liquor were used as detergents.
• the washing time was 30 minutes.
• the bleaching effect was determined as an increase in remission on the various test tissues.
• the evaluation was carried out in a known manner.

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• Chemical & Material Sciences (AREA)
• Inorganic 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 Chemistry (AREA)
• Detergent Compositions (AREA)
• Dental Preparations (AREA)

Applications Claiming Priority (2)

Publications (3)

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• 1988
  • 1988-12-14 DE DE3842008A patent/DE3842008A1/de not_active Withdrawn
• 1989
  • 1989-12-09 DE DE58909648T patent/DE58909648D1/de not_active Expired - Fee Related
  • 1989-12-09 EP EP89122759A patent/EP0373546B1/fr not_active Expired - Lifetime
  • 1989-12-09 ES ES89122759T patent/ES2087070T3/es not_active Expired - Lifetime
  • 1989-12-09 AT AT89122759T patent/ATE136580T1/de not_active IP Right Cessation
  • 1989-12-12 JP JP1320740A patent/JPH02202600A/ja active Pending
  • 1989-12-13 CA CA002005331A patent/CA2005331A1/fr not_active Abandoned
  • 1989-12-13 US US07/449,990 patent/US5045222A/en not_active Expired - Fee Related

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