Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
  • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
  • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
  • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
  • C07H13/06—Fatty acids
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
  • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
  • C07H15/02—Acyclic radicals, not substituted by cyclic structures
  • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
  • C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty acid
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
  • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
  • C07H15/02—Acyclic radicals, not substituted by cyclic structures
  • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
  • C07H15/08—Polyoxyalkylene derivatives
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
  • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
  • C08G65/2615—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
  • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
  • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
• • 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
  • C11D1/662—Carbohydrates or derivatives
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
  • D06B11/00—Treatment of selected parts of textile materials, e.g. partial dyeing
  • D06B11/0056—Treatment of selected parts of textile materials, e.g. partial dyeing of fabrics
  • D06B11/0069—Treatment of selected parts of textile materials, e.g. partial dyeing of fabrics by continuous contact with a member able to bring simultaneously a plurality of treating materials
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
  • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
  • Y10S516/06—Protein or carboxylic compound containing

Definitions

• Sucroglycerides are obtained in known manner (US. Patent No. 2,893,990) by transesterification, in a solvent, of natural triglycerides like lard oil, tallow, coconut, palm oil, palmist oil etc., or synthetic triglycerides, with sucrose in the presence of an alkaline catalyst, such as alkali metal hydroxides and carbonates. During the reaction, one or more acid residues of the glycerides are split and react to fix one or more alcoholic hydroxyls of the sucrose, so that it is esterified. In this way a series of products is obtained having different contents of combined sugar, depending on the quantity of sucrose present in the transesterification.
• an alkaline catalyst such as alkali metal hydroxides and carbonates
• sucroglycerides which are thus composed, in different proportions, of monoesters of sucrose with the different fatty acids contained in the starting glyceride, monoand diglycerides or their mixtures (depending on the quantity of fatty acid residues removed from each mole of the starting glyceride) and variable proportions of unreacted triglyceride.
• Sucroglycerides are in general water-insoluble products which are, however, easily dispersible; they possess lypophilic properties and consequently, not being particularly good emulsifiers, have comparatively low wetting and detergent properties.
• the oxyethylation of synthetic organic products, such as alkylphenols and higher fatty alcohols, or of natural products, such as higher fatty acids and their glycerides, makes it possible to obtain surfactant agents possessing detergent, wetting, foaming and emulsifying properties which vary according to the properties of the starting material and the number of moles of ethylene oxide introduced for each mole of such starting material.
• the various oxyethylenated sucroglycerides if the reaction conditions and the reactants proportions have always been the same, have the same composition whatever was the initial fatty ester used.
• These reaction conditions consist in a transesterification reaction between a triglyceride and sucrose in a molar ratio varying between l:0.5 and 1:6, using as solvent dimethylformamide Patented Oct. 4, 1966 ice in the presence of an alkaline catalyst which may be sodium or potassium carbonate; the temperatures have to be maintained in a range of to 120 C. for 2-10 hours.
• the oxyethylenation of the so obtained sucroglycerides is conducted in absence of solvents introducing ethylene oxide in proportions varying from 0.5 to 9 parts per one part in weight of the sucroglyceride.
• the weight ratio between ethylene oxide and the sucroglyceride is 2:1.
• the temperature which is commonly used for this kind of reaction is comprised between 140 and 160 C. As this would compromise the stability of the sucroglyceride we have found that the temperature must be lowered down about to 130.
• the synergistic activity of the oxyethylenated sucroglycerides has been performed confronting the oxyethylenated tallow sucroglyceride (TOSG) and the oxyethylenated coconut sucroglyceride (COSG) with their single components. Both of the oxyethylenated sucroglycerides have been obtained reacting sucrose and coconut glyceride (respectively tallow glyceride) in a ratio 0.5 :1 and condensing then 1 part in weight of the obtained compound with 2 parts of ethylene oxide.
• TOSG oxyethylenated tallow sucroglyceride
• COSG oxyethylenated coconut sucroglyceride
• compositions g. have been dissolved in 1 liter of water (that is a 5% solution of active principle) and the cleaning power of the solution assayed in a Launder- Ometer apparatus against cotton dirtied in a standard way.
• the washings have been performed at a temperature of 50 C., for a time of 60 minutes.
• the dirt removed was evaluated with the Lange leucometer. The data are collected in the table 1.
• the commercially available detergents had the composition:
• the detergency assays were performed in a Launder- Ometer at a temperature of 50 C. for 60 minutes.
• the tissue used was cotton dirtied in a standard way with China ink and olive oil.
• the whiteness of the cleaned tissue was evaluated with the Lange leucometer and expressed in percent of removed dirt (average values).
• the data are collected in the Table 2 in two columns according to the quantity per liter of the detergent.
• a second series of assays was performed on dirty cotton linen using a 5% TOSG mixture in the builders described in column 2 and compared with a detergent consisting of the same builders and including a 5% of oleocetyl alcohol oxyethylenated 1:25 (OOC).
• OOC oleocetyl alcohol oxyethylenated 1:25
• Table 3 collects the average data in percent of dirt removed, resulting from Q. a photocolorimetric measurements on blank tissues with standard dirt (TNO Delft test).
• the biodegradability is a property which is now becoming a fundamental request for a good detergent.
• the oxyethylenated sucroglycerides possess in high degree these properties. The foam is practically unnoticeable at normal temperatures, while assays on their biodegradability show that the bacteria present in the waste water destroy them very rapidly.
• the biodegradability of oxyethylenated sucroesters has been evaluated by determining the growth of the number of bacteria and the degradation of the detergent.
• Example 1 Into a reaction chamber for oxyethylation introduce 100 kg. of tallow sucroglyceride with a content of combined sugar of and 0.800 kg. of sodium hydroxide. Heat at 90 C. and introduce during 4 hours 200 kg. of ethylene oxide.
• the temperature must be regulated so as to have at the end of the reaction a maximum temperature of 120 C.
• the condensation product is a light brown oily liquid quite and quickly soluble in water, with a cloud point of 93 C. (in solution at 1% concentration in distilled water).
• Example 2 Proceed as in Example 1 introducing during 4 hours 300 kg. of ethylene oxide instead of 200.
• the condensation product is a light brown oily liquid, very soluble in water, with a cloud point of 96 C.
• Example 3 Proceed as in Example 1, using coconut oil sucroglyceride with a content of sucrose of Add 0.750 kg. of potassium hydroxide to the 100 kg. of sucroglyceride. Reaction is started at 80 C. and the quantity of ethylene oxide is in the ratio 2:1 in comparison with the starting total weight. The final temperature is 120 C. The total duration of the condensation is 5 hours.
• the obtained product (300 kg.) is composed of a pale yellow oily liquid quite soluble in water with a gently foaming solution and with a cloud point at 92 C. (1% solution in distilled water).
• Example 4 Proceed as in Example 3, reacting ethylene oxide in a ratio of 3: 1, in weight to the sucroglyceride.
• the product is a pale yellow oil very soluble in water. Cloud point at 97 C.
• Example 5 Into a reaction chamber for oxyethylation introduce 95 kg. of lard sucroglyceride with a content of combined sugar of 25%, 5 kg. of refined tallow and 0.150 kg. of sodium hydroxide. Heat at 90 C. and introduce during 4 hours time 300 kg. of ethyleneoxide.
• the temperature must be regulated so as to have at the end of the reaction a maximum temperature of 120 C.
• the condensation product is a light brown oily liquid quite and quickly soluble in water, with a cloud point of 100 (in solution at 1% concentration).
• Example 5 using coconut oil sucroglyceride with a content of sucrose of 30%. Add 5 kg. of palmist oil and 0.150 kg. of potassium hydroxide to the 95 kg. of sucroglyceride. Reaction is started at C. and the quantity of ethyleneoxide is in the ratio 3:1 in comparison with the starting total weight. The final temperature is 120 C. The total length of the condensation is 5 hours.
• the obtained product (400 kg.) is composed of a pale yellow oily liquid quite soluble in water with a greatly foaming solution and with a cloud point at 102 (1% solution in water).
• Example 7 Proceed in the same way as in Example 5, provided that the ethyleneoxide introduced is in the ratio of 9:1 on the weight of the mass of lard sucroglyceride and lard. The length of the condensation is 7 hours. The final product obtained is a soft, waxy, ivory-colored mass, quite soluble in water with a cloud point of 110 (1% solution in salt water).
• a condensation product of coconut sucroglyceride with 0.5 to 9 parts by weight of ethylene oxide 1.
• Condensation product of 1 part by weight of coconut sucroglyceride composed of 0.5 part by weight of sucrose to 1 part by weight of coconut glyceride, with 2 parts by weight of ethyleneoxide.
• Condensation products of sucroglycerides with about 3 to 9 parts by weight of ethyleneoxide prepared in the presence of about 5 parts of triglyceride to parts of the sucr-oglyceride and in the presence of an alkali metal hydroxide, said products having surfactant, detergent, and emulsifying properties, and having a cloud point in 1% aqueous solution of about 100 to 7.

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Citations (2)

• 0
  • BE BE633543D patent/BE633543A/xx unknown
  • IT IT650398D patent/IT650398A/it unknown
  • NL NL144166D patent/NL144166C/xx active
• 1962
  • 1962-04-11 GB GB14037/62A patent/GB999554A/en not_active Expired
  • 1962-04-20 LU LU41585D patent/LU41585A1/xx unknown
  • 1962-04-27 SE SE4742/62A patent/SE302456B/xx unknown
  • 1962-04-27 CH CH506262A patent/CH423741A/fr unknown
• 1963
  • 1963-05-13 AT AT384663A patent/AT241658B/de active
  • 1963-05-13 GB GB18904/63A patent/GB1013988A/en not_active Expired
  • 1963-06-01 LU LU43851D patent/LU43851A1/xx unknown
  • 1963-08-07 CH CH975763A patent/CH455114A/fr unknown
  • 1963-09-19 SE SE10253/63A patent/SE326787B/xx unknown
• 1964
  • 1964-01-28 US US340807A patent/US3277080A/en not_active Expired - Lifetime
  • 1964-02-07 NL NL6401005A patent/NL6401005A/xx unknown

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