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WO1997018243A1 - Saccharides agents tensioactifs - Google Patents

Saccharides agents tensioactifs Download PDF

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Publication number
WO1997018243A1
WO1997018243A1 PCT/US1996/018493 US9618493W WO9718243A1 WO 1997018243 A1 WO1997018243 A1 WO 1997018243A1 US 9618493 W US9618493 W US 9618493W WO 9718243 A1 WO9718243 A1 WO 9718243A1
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Prior art keywords
saccharide
surfactant
group
surfactants
chain
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PCT/US1996/018493
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WO1997018243A9 (fr
Inventor
Roger E. Marchant
Tianhong Zhang
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Case Western Reserve University
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Case Western Reserve University
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Priority to AU77380/96A priority Critical patent/AU7738096A/en
Publication of WO1997018243A1 publication Critical patent/WO1997018243A1/fr
Anticipated expiration legal-status Critical
Publication of WO1997018243A9 publication Critical patent/WO1997018243A9/fr
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    • 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
    • C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0021—Dextran, i.e. (alpha-1,4)-D-glucan; Derivatives thereof, e.g. Sephadex, i.e. crosslinked dextran
    • 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
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • 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

Definitions

  • the present invention relates to surfactants, primarily saccharide surfactants.
  • Surfactants are compounds which reduce the interfacial tension between a gas and a liquid, for example air and water, between two different liquids, or between a liquid and a solid. Because of their surface-active properties, surfactants are useful as detergents, wetting agents, solubilizing agents, dispersing agents, or emulsifiers. Surfactants which are soluble in water are especially useful as wetting agents. Wetting agents enhance the ability of water or a water ⁇ olution to penetrate into or to spread over the surface of another material and include surfactants which are amphophilic. Surfactants which promote the formation of a stable mixture of two immiscible liquids are also useful as emulsifiers.
  • the emulsion that i ⁇ formed depends upon the characteristics of the particular surfactant used and can be either an oil in water-type emulsion, where water is the continuous phase and the oil is the disperse phase, or a water in oil-type emulsion in which oil forms the continuous phase and water droplets form the dispersed phase.
  • surfactants which are able to maintain the phase separation of the emulsion, especially at elevated temperatures, are especially useful as emulsifiers.
  • the present invention provides new saccharide surfactants.
  • the saccharide surfactants include diblock saccharide surfactants and triblock saccharide surfactants.
  • Diblock saccharide surfactants have a hydrophobic segment bonded to a hydrophilic head group, that is a saccharide chain.
  • the triblock saccharide surfactants have a hydrophobic segment bonded to two hydrophilic saccharide chains.
  • the hydrophobic segments of the diblock and triblock saccharide surfactants comprise at least one alkyl chain having 5 to 20 carbon atoms, preferably 6 to 18 carbon atoms more preferably 8 to 18 carbons.
  • the saccharide head groups/chains include monosaccharides, disaccharide ⁇ , and oligosaccharides .
  • the saccharide head group/chain comprises 2 to 12 sugar residues, more preferably 2 to 10 sugar residues.
  • the diblock and triblock saccharide surfactants typically are soluble in water and reduce the surface tension of aqueous solutions. Accordingly, the water-soluble diblock and triblock saccharide surfactants are useful as wetting agents.
  • the diblock and triblock saccharide surfactants are also useful to form oil-in- water type emulsions.
  • the diblock and triblock saccharide surfactants also associate with hydrophobic polymeric substrates, and are useful for modifying the surface characteristics of hydrophobic substrates. Accordingly, the diblock and triblock saccharide surfactants are useful for reducing friction and providing resistance to protein adsorption of the hydrophobic substrate. Such uses may have broad application in biomedical or bioseparation systems.
  • the saccharide surfactants of the present invention include diblock saccharide surfactants and triblock saccharide surfactants.
  • the diblock saccharide surfactants have a hydrophobic segment comprising at least one alkyl chain and a hydrophilic head group comprising a saccharide chain.
  • the saccharide chains of the diblock saccharide surfactants include monosaccharides, disaccharides, and oligosaccharides.
  • the saccharide chains have from 2 to 12 sugar residues, preferably from 2 to 10 sugar residues and have a weight average molecular weight (M w ) ranging from about 300 to less than 4000, preferably from about 300 to about 3500, more preferably from about 300 to 2000.
  • the alkyl chains of the diblock saccharide surfactants have from about 5 to 20 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 8 to 18 carbon atoms .
  • the triblock saccharide surfactants comprise: a hydrophobic segment comprising at least one alkyl chain; and two hydrophilic head groups each comprising a saccharide chain.
  • the saccharide chains of the triblock polymers include monosaccharides, disaccharides, and oligosaccharides.
  • the saccharide chains have 2 to 12 sugar residues, preferably 2 to 10 sugar residues and a weight average molecular weight (M w ) ranging from about 300 to less than 4000, preferably from about 300 to about 3500, more preferably from about 300 to 2000.
  • the alkyl chains of the triblock saccharide surfactants have 5 to 20 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 8 to 18 carbon atoms.
  • the hydrophobic segment and hydrophilic head groups are joined by a linkage group.
  • the preferred linkage group is CONH.
  • the present invention also provides a method for forming and isolating nonionic saccharide surfactants in which the hydrophilic saccharide chains are linked to the hydrophobic alkyl chains by an amide group, that is, a CONH group. In general, the method involves oxidation of the saccharide in an aqueous solution containing iodine and potassium hydroxide.
  • the mixture is then passed through a cationic exchange column to convert the potassium salt form of the saccharide to the acidic form of the saccharide.
  • the eluate from the column is then lyophilized to give the lactone form of the saccharide.
  • the lactonized saccharide is dissolved in DMSO and an alkylamine added to the solution.
  • the solution is heated to 60°C for a time and temperature sufficient to form the diblock saccharide surfactant.
  • the reaction products are then precipitated with chloroform and dried under vacuum at 60°C.
  • the resulting powder is dissolved in water and passed through a weak anionic exchange column.
  • the lactonized saccharide is dissolved in DMSO and an alkyldiamine added to the solution.
  • the solution is heated to 60°C until the triblock saccharide is formed.
  • the products are precipitated from the solution with chloroform, dried under vacuum at 60°C, and passed through a weak anionic exchange column and a weak cationic exchange column.
  • MAL-C6 N-n-Hexyl-D-maltonamide
  • the eluate was filtered, and the filtrate again was passed through a regenerated Amberlite IR-120 resin column to convert silver altonate to D-maltonic acid.
  • the altonic acid solution was concentrated and lyophilized to give 1.53 g (90% yield) of D-maltonolactone.
  • To a 10 mL DMSO solution containing 0.68 g (2.0 mmol) of D- altonolactone was added 2.02 g (20 mmol) of hexylamine from Aldrich Chemical Co. The reaction solution was stirred at 60°C for 2 days and then concentrated to 2 L by vacuum distillation. The product was precipitated in chloroform.
  • the eluate was concentrated and lyophilized to give 2.40 g (87% yield) of dextran lactone.
  • To a 4 mL DMSO solution containing 0.55 g (0.4 mmol) of dextran lactone was added 2.02 g (20 mmol) of hexylamine .
  • the reaction solution was stirred at 60°C for 4 days, and the product was precipitated in chloroform.
  • the precipitate was filtered and dried under vacuum at 60°C overnight to give a white powder.
  • the powder was dissolved in 50 L of water and passed through a weak anionic exchange column packed with Amberlite IRA-94 resin.
  • the eluate was concentrated and lyophilized to give 0.30 g (50% yield) of N-n-Hexyldextran Aldonamide (DEX9-C6) .
  • Example 5 Synthesis of N-n-Dodecyl-dextran aldonamide (DEX9-C12) .
  • DEX9-C12 N-n-Dodecyl-dextran aldonamide
  • Example 7 Synthesis of N, N -Hexamethylenebis (dextran aldonamide) (DEX-C6-DEX) .
  • DEX-C6-DEX N, N -Hexamethylenebis (dextran aldonamide)
  • Example 8 Synthesis of ⁇ , ⁇ ' -Dodecamethylene-bismaltonamide (MAL- C12-MAL) .
  • MAL- C12-MAL DMSO solution containing 1.70 g (5 mmol) of maltonolactone.
  • 0.40 g (2 mmol) of 1, 12-dodecanedia ⁇ nine was added. The mixture was stirred at 60°C for 48 hours and then concentrated to a light brown viscous residue by vacuum distillation. The residue was washed with chloroform to yield light yellow powder.
  • the powder was purified by fla ⁇ h chromatography using neutral alumina gel as packing material and a water/ ethanol mixture [%] as eluent to give 0.80 g (59% yield) of ⁇ , ⁇ ' -Dodecamethylene- bismaltonamide (MAL-C12-MAL) .
  • Example 9 Synthesis of ⁇ , ⁇ ' -Dodecamethylene-bis (dextran aldonamide) (DEX-C12-DEX) .
  • DEX-C12-DEX ⁇ , ⁇ ' -Dodecamethylene-bis (dextran aldonamide)
  • MAL-C8 maltonolactone was reacted with ocytlamine from Aldrich Chemical Company and i ⁇ olated from the reaction mixture according to the procedures described above for N-Octylmaltonamide (Mal-C8) .
  • Example 11 Synthesis of N-Decylmaltonamide (Mal-ClO) .
  • MAL-CIO maltonolactone was reacted with decylamine from Aldrich Chemical Company and isolated from the reaction mixture according to the procedures described above for N-Decylmaltonamide (Mal-ClO) in Example 4.
  • Example 12 Synthesis of N-Octydecylmaltonamide (Mal-C18) .
  • maltonolactone was reacted with octydecylamine from Aldrich Chemical Company and isolated from the reaction mixture according to the procedures described above for N-Octydecylmaltonamide (Mal-C18) as in Example 4.
  • Example 13 Synthesis of N-n-Octydecyl-dextran Aldonamide (Dex 9- C18) .
  • dextran lactone was reacted with octydecylamine and isolated from the reaction mixture according to the procedures described above for N-n-dodecyl-dextran aldonamine of example 5.
  • the structures of the saccharide surfactants were confirmed using fourier transform infra red (FTIR) spectroscopy and H- nuclear magnetic resonance spectroscopy ( -NMR) .
  • FTIR Fourier transform infra red
  • -NMR H- nuclear magnetic resonance spectroscopy
  • FTIR spectroscopy FTIR spectroscopy. Solutions were cast on KBr disks and dried under vacuum before measurements. Powdered materials were ground with KBr powder and pressed into pellets under reduced pressure. Transmission IR spectra in the range 400-4000 cm "1 were recorded using a Digilab FTS-40 FTIR spectrometer. For each sample, 256 scans were collected with a resolution of 8 cm '1 . FTIR spectroscopy demonstrated that the representative compound maltonic acid was converted quantitatively to D- maltonolactone by lyophilization.
  • the -NMR spectra of D-maltose shows a proton peak at 6.67 ppm which is due to the anomeric hydroxyl.
  • the 1 H-NMR spectra of MAL-C6 (example 1) and MAL-C6-MAL (example 6) show new proton peaks due to CONH at 7.58 ppm, C0NHCH 2 at 3.09 ppm, and (CH 2 ) 4 at 1.20- 1.40 ppm, while the proton peak related to the anomeric po ⁇ ition in maltose is absent. These proton peaks are indicative of successful reactions and purification.
  • the only difference between the X H-NMR spectra of MAL-C6 and MAL-C6-MAL is proton peaks derived from the hydrocarbon segments, that is, hexamethylene vs n-hexyl.
  • the X H-NMR spectra of dextran shows a proton peak due to the anomeric OH at 6.32-6.65 ppm.
  • Example 8 ⁇ 1.20-1.40 (20H, -(CH 2 ) 10 -) , 3.09-4.00 (28H, -CONH- CH 2 - and all maltose CH's and CH 2 's except the one at glycosidic linkage) , 4.48-5.56 (18H, C-H at glycosidic linkage and all -OH' ⁇ ) , 7.58 (2H, -CONH-) ;] and Example 9, ⁇ 1.20-1.40 (- ⁇ CH 2 ) 10 , 3.00-4.04 (-CONH-CH 2 .
  • a cloud point temperature for the sample saccharide surfactants, all of the water soluble saccharide surfactants including DEX-C12 were dissolved in water at a concentration of 1% and heated to various temperatures up to 100°C
  • the cloud point temperature is the temperature at which a hydrophilic surfactant forms large aggregates. The formation of aggregates is believed to be due to dehydration of the surfactant. No cloud points were observed for any of the soluble saccharide surfactants. This indicates that the degree of hydration of the saccharide chains of the block surfactants is sufficient to prevent phase separation even at high temperatures.
  • REDUCING SURFACE TENSION OF AQUEOUS SOLUTIONS WITH SACCHARIDE SURFACTANTS Surface tension reduction is one of the characteristic properties that water-soluble surfactants exhibit in aqueous solution.
  • the reduction in surface tension results from the replacement of water molecules at the water/air interface by surfactant molecules.
  • the saccharide surfactants are oriented so that the hydrophobic segment ⁇ are exposed to the air at the interface and the hydrophilic head groups are in the aqueous environment.
  • the concentration of surfactant in the solution is increased, the surface density of the surfactant also increases until the interface becomes saturated with surfactant molecules.
  • CAC critical adsorption concentration
  • the first inflection point which occurs at low concentrations of MAL-C12-MAL is related to the formation of premicelles with small aggregation number and that the second inflection point, which occurs at high concentrations of MAL-C12-MAL in the aqueous solution, is related to the formation of true micelles and, thus, represents the CMC.
  • the surface tension plot for the triblock surfactant DEX-C12-DEX exhibited one inflection point which correlated to premicelle formation. However, no second inflection point corresponding to CMC was observed for DEX-C12-DEX even when the concentration was increased to 100 mg/ml.
  • the CMC of triblock saccharide surfactants which form micelles are higher than the CMC values of corresponding diblock saccharide surfactants.
  • the CMC values for the diblock and triblock saccharide surfactants are summarized in Table 1.
  • the Gibbs adsorption equation relates the surface 9 (excess; concentration of the surfactant, r, to the surface tension 0 and the surfactant chemical potential. 7 is calculated from the 1 slope cf the d-y/dlogC plot when the concentration is below CMC. 2
  • concentration concentration of the surfactant, r
  • 7 is calculated from the 1 slope cf the d-y/dlogC plot when the concentration is below CMC. 2
  • the bulk concentration is much 3 smaller that the concentration at the interface, so r is 4 practically the same as the surface density of the monolayer. 5
  • the area occupied per molecule of 6 surfactant is approximately l/T.
  • ote ata in parentnes s were oD aine ⁇ a premice e stage.
  • the triblock surfactants occupy a greater 2 surface area tnan the corresponding diolock surfactants, especially 3 at low concentrations of triblock surfactant
  • concentration 4 of the tribloc surfactant increases, the area occupied per 5 molecule of surfactant decreases
  • the surface area 6 per molecule of MAL-C12-MAL at the water/air interface ⁇ ecreased 7 from 71 to 49 A" as the solution went through tne premiceiie and 8 micelle stages
  • the sugar residues per unit area 9 increased significantly when a second oligosaccna ⁇ de segment was 0 added to the hydrophobic segment
  • the sugar residues 1 per unit went from 14.8 for DEX9-C12 to 19.6 for DEX9-C12-DEX9.
  • MAL-C6 nad the 3 lowest ⁇ urface concentration and largest surface area per molecule. 4 The high surface area per molecule of MAL-6 s believed tc be due 5 to weak interactions between the hexyl chains For the other 6 maltose-based diblock surfactants, the surface areas occupied by 7 each molecule are quite similar 8 As shown in Table 2, significant changes in surface 9 concentration and surface area per molecule were observed when the 0 size of the hydrophilic saccharide chain was changed while the size 1 of the alkyl chain was kept constant A comparison of surface area per molecule of MAL-C12 and DEX-C12 demonstrates a significant increase in surface area per molecule when the size of the saccharide chain was increased from 2 sugar residue ⁇ to 9 ⁇ ugar residues.
  • the higher surface area occupied by the latter surfactant is believed to be attributed to the larger hydrophilic chain.
  • the surfactant density at the air/water interface is decreased by increasing oligosaccharide chain length and by changing the molecular geometry of the surfactants from the diblock to triblock type.
  • these same changes in surfactant structure substantially increased the overall sugar density at the air/water interface.
  • the surface tension reduction property of the block surfactants were usually evaluated by their efficiency and effectiveness.
  • the efficiency of a surfactant is the concentration of surfactant required to reduce ⁇ urface tension to a certain value.
  • Effectiveness which does not always follow the same trends as efficiency, is the maximum reduction in ⁇ urface ten ⁇ ion that a certain surfactant can achieve regardless of concentration.
  • the efficiencies of the diblock and triblock saccharide surfactants were evaluated by determining the pC20, or the value of the negative logarithm of the bulk concentration necessary to reduce the surface tension by 20 dynes/cm.
  • the effectiveness of the diblock and triblock saccharide surfactant ⁇ were evaluated by determining the Trcmc, which i ⁇ the extent of surface tension reduction attained at the CMC.
  • the concentration of DEX-C12 and DEX-C12-DEX required to reduce the surface tension of water by 50 dynes/cm was 2 mg/ml and 0.2 mg/ml, respectively. Since the molecular weight of the triblock surfactant is about twice that of the diblock surfactant, this indicates that DEX-C12 is about five times as efficient as DEX-C12-DEX in reducing surface water tension. As shown in Table 3, the effectiveness in reducing surface tension did not change with differences in the hydrophobic chain length.
  • Trcmc is almost constant for N-alkylmaltonamides with different alkyl chain lengths because log (cmc/c, l20 ) and r change in opposite directions at approximately the same rate with the change of hydrophobic chain length.
  • DEX-C6 is almost as effective at reducing water surface tension as DEX-C12
  • DEX-C6-DEX is almost as effective as the DEX-C12-DEX at reducing water surface tension.
  • the size of the saccharide chain length had a significant effect on the effectiveness of the diblock surfactants in reducing surface ten ⁇ ion, as demonstrated by comparing the rrcmc values for MAL-C12 and DEX9-C12 shown in Table 3.
  • the effect of hydrophobic/alkyl chain length on the surface reduction properties of the saccharide surfactants is also shown by comparing the efficiencies of DEX-C6 and DEX-C12-DEX. In DEX-C6 and DEX-C12-DEX the ratio of hydrophobic/alkyl chain length to hydrophilic/saccharide chain length for each of these surfactants is the same.
  • the triblock saccharide surfactants have higher critical micelle concentrations than diblock saccharide surfactants with the same size hydrophobic/alkyl segments and hydrophilic saccharide chains.
  • diblock saccharide surfactants are more efficient at reducing surface water tension than the corresponding triblock surfactant, i.e., having the same size alkyl chain and saccharide chain.
  • the triblock is more efficient than the diblock in reducing surface tension.
  • Emulsions were prepared with the saccharide surfactant ⁇ by vortexing a l/l volume ratio octane/water mixture containing 2% surfactant at 3000 rpm for 1 hour using a Vortex Geni II Mixer.
  • the emulsion type was determined by the dilution method.
  • the emulsion stability was analyzed over a one week period at room temperature by visual observation.
  • the types and stability of the emulsions prepared using the saccharide surfactants is ⁇ hown in Table 4.
  • Emulsion Stability c
  • the emulsion type formed by the saccharide surfactants is an oil in water (o/w emulsion) .
  • the emulsion dispersed readily in water but did not disperse in octane.
  • PE films were rinsed several times with distilled water and soaked in the aqueous solution ⁇ containing the diblock and triblock saccharide surfactants of examples 2, 5, 7 and 9 at a concentration of 1 mg/ml for different time periods.
  • the polyethylene films were also immer ⁇ ed in aqueous solutions containing different concentrations of the surfactants for 24 hours at 25°C.
  • the PE films were then washed with distilled water three times and air dried in a class 100 clean hood overnight. Control films were soaked in distilled water or aqueous solutions of dextran at a 1% concentration.
  • the surface oxygen and carbon concentration of the control and surfactant-treated films were measured by X-ray photon spectroscopy (XPS) using a Perkin Elmer PHI-5400 ESCA system.
  • the X-ray source was magnesium and the pass energy was 89.75 eV.
  • the experiments were carried out at a take-off angle of 45 degrees.
  • At least three films were tested for each surfactant concentration and the average error is within 2%. The average values were reported.
  • the polyethylene films were removed from aqueous solutions containing 1 mg/ml of the saccharide surfactants at various time points and the films examined by XPS. The results of these studies indicated that adsorption of the surfactants to the PE films reached equilibrium after several hours.
  • the XPS survey scans of the control polyethylene film soaked in an aqueous solution of 1 mg/ml dextran were compared to the XPS survey scans of the polyethylene films treated with aqueous solutions containing lmg/ml of the diblock and triblock surfactants DEX-C12 and DEX-C12-DEX.
  • aqueous solutions containing lmg/ml of the diblock and triblock surfactants DEX-C12 and DEX-C12-DEX As expected, only about 1% oxygen was observed on the control film soaked in a dextran solution. In contrast, significantly higher oxygen concentrations were observed for the PE films treated with the dextran-based surfactants, establishing the adsorption of surfactant molecules on the PE film.
  • the driving force for the adsorption of surfactant is most likely the hydrophobic interaction between the hydrophobic dodecamethylene segment and the hydrophobic PE surface.
  • the ⁇ urface oxygen concentration on surfactant treated PE surfaces was plotted against surfactant concentration.
  • the oxygen concentration increased with increasing concentration of surfactant until the interface became saturated with surfactant molecules.
  • the oxygen concentration on the polyethylene treated with the diblock surfactant was slightly greater than the oxygen concentration of the PE film treated with the triblock surfactant.
  • hydrophobic surfaces can be made hydrophilic by simple adsorption of dextran surfactants to the hydrophobic surface. Since it is much easier to alter the hydrophobic surfaces by adsorption of saccharide surfactants than by surface chemical derivation, physiosorption of surfactants on hydrophobic surfaces should be a highly desirable method for altering the hydrophobicity of hydrophobic substrates. While the invention has been described to some degree of particularity, various adaptations and modifications can be made without departing from the scope of the invention a ⁇ defined in the appended claims.

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Abstract

La présente invention concerne des saccharides agents tensioactifs. Ces saccharides tensioactifs rassemblent des saccharides tensioactifs biblocs et des saccharides tensioactifs triblocs. Les saccharides tensioactifs biblocs comportent un segment hydrophobe lié à un groupe de tête hydrophile, à savoir une chaîne saccharide. Les saccharides tensioactifs triblocs comportent un segment hydrophobe lié à deux chaînes hydrophiles saccharides tensioactifs. Les segments hydrophobes des saccharides tensioactifs diblocs et triblocs comprennent au moins une chaîne alkyle portant de 5 à 20 atomes de carbone, de préférence de 6 à 18 atomes de carbone, et plus préférentiellement encore de 8 à 18 atomes de carbone. Les groupes ou chaînes de tête de saccharides incluent des monosaccharides, des disaccharides et des oligosaccharides, et leur masse moléculaire moyenne se trouve dans une plage inférieure à 4000. De préférence, les groupes ou chaînes de tête de saccharides comprennent 2 à 12 groupes sucre. De préférence, les groupes de tête sont liés aux chaînes alkyle au moyen d'un groupe amide.
PCT/US1996/018493 1995-11-14 1996-11-13 Saccharides agents tensioactifs Ceased WO1997018243A1 (fr)

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US60/006,704 1995-11-14

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
US6541270B2 (en) * 2001-01-16 2003-04-01 The United States Of America As Represented By The Secretary Of The Navy Method, detector, and apparatus for colorimetric detection of chemical and biological agents

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WO1994011411A1 (fr) * 1992-11-19 1994-05-26 Case Western Reserve University Surfaces d'implants non thrombogenes
WO1995027770A1 (fr) * 1994-04-08 1995-10-19 Unilever Plc Compositions detergentes contenant des aldobionamides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994011411A1 (fr) * 1992-11-19 1994-05-26 Case Western Reserve University Surfaces d'implants non thrombogenes
WO1995027770A1 (fr) * 1994-04-08 1995-10-19 Unilever Plc Compositions detergentes contenant des aldobionamides

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US6541270B2 (en) * 2001-01-16 2003-04-01 The United States Of America As Represented By The Secretary Of The Navy Method, detector, and apparatus for colorimetric detection of chemical and biological agents

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