Classifications

• • 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
  • C07H15/20—Carbocyclic rings
  • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K3/00—Materials not provided for elsewhere
• • C—CHEMISTRY; METALLURGY
  • C40—COMBINATORIAL TECHNOLOGY
  • C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
  • C40B40/00—Libraries per se, e.g. arrays, mixtures

Definitions

• the present invention relates to a gelling agent having a gel forming ability for both an organic solvent and water.
• Conventional technology
• aqueous gels are usually made of macromolecules such as proteins and polymers, are one-dimensional aggregates of low molecular weight and have a reversible higher-order structure formed by self-aggregation. Unlike this, it is difficult to identify this complex interaction. However, there are a few "aqueous gels" consisting of such aggregates of low molecular weight compounds (Estroff, LA; Hamilton, AD Angew. Chem. Int. Ed. 2000, 39, 3447 .: Fuhrhop).
• the present inventors have designed several gelling agents, and by conducting such an analysis on them, have conducted research on Gerich agents having excellent gel-forming ability in both organic solvents and water. Was. Means for solving the problem
• the present inventors have already found that a gelling agent derived from glucose gels water / alcohol (volume ratio 1: 1) or water / acetone (volume ratio 1: 1) (John, G .; Masuda, Okada, Y .; Yase, K .; Shimizu, T. Adv. Mater. 2001, 13, 715.).
• This finding suggests that if we carefully study sugars as well as the appropriate hydrophobic groups, we may find that some novel aqueous gelling agents may be found. It can be useful to identify what are the basic structural requirements for designing a design. Under such a purpose, a novel gelling agent having a bran portion, an aminophenyl and a long-chain alkyl group was designed.
• A represents a sugar residue and R represents an alkyl group.
• R represents an alkyl group.
• the hydrogelator represented by the formula has excellent gel-forming ability with respect to both organic solvents and water.
• the long-chain alkyl group which forms one end of this gelling agent enhances the solubility in organic solvents.
• the assembly of fibers is promoted by van der Waalska, and finally a gel is formed.
• FIG. 1 is a view showing an EF-TEM photograph of an aqueous gel prepared using the gelling agent of the present invention.
• FIG. 2 is an EF-TEM photograph of an aqueous gel produced using the gelling agent of the present invention, and is an enlarged view of FIG. Arrows indicate helical fibers.
• FIG. 3 is a view showing an SEM photograph of an aqueous gel prepared using the gelling agent of the present invention.
• FIG. 4 is a 1 H-NMR spectrum of an aqueous gel in D 20 and methanol-d 4 (volume ratio: 1 Z 1).
• Figure 5 shows the XRD spectrum of xerogel.
• FIG. 6 is an XRD spectrum of the aqueous gel.
• FIG. 7 is a view showing a state of self-aggregation of the aqueous gel.
• the hide mouth gelling agent of the present invention has the following chemical formula
• A represents a sugar residue.
• the saccharide may be any of monosaccharides, oligosaccharides, and polysaccharides, but is preferably a monosaccharide.
• the monosaccharide include hexoses such as gnorecose, galactose, N-acetyl / glucosamine, and pentoses of L-arabinosidoxylose! /, But deviations are possible, but aldopyranoses are particularly preferred. There are two types of viranose, Hihiro and Hana.
• D-Gnoreco-pyranoside p-D-galactopyranoside a-D-Galactopyranoside, p-Nitrophenylenol CK-D-Mannopyranoside, p-D-g-phenyl- ⁇ -D —Gnorecopyranoside, ⁇ -Nitrofueni / re) 3—D—Galactoviranoside, ⁇ —-Furouru ⁇ _D—Mannoviranoside, and the like.
• aldopyranose dalcoviranose or galactopyranose is preferable.
• residue refers to a residue obtained by removing a hydrogen atom of a hydroxyl group of a sugar, but is preferably a residue obtained by removing a hydrogen atom of a hydroxyl group having a force V ”bonded to a 6-membered ring of aldoviranose. Represents a group.
• R in the above formula represents an alkyl group.
• This alkyl group may be straight or branched, but is preferably straight.
• the number of carbon atoms is preferably from 6 to 20 and more preferably from 10 to 20.
• the hide mouth gelling agent of the present invention can harden a large amount of water with a small amount of a solid gelling agent, and therefore can retain water (such as desert greening, water retaining agent for plant cultivation soil) and water.
• Solidifies fuel solids, organic solvents and oils as an alcohol-retaining agent because it absorbs absorbents (urine absorbents for pet toilets, sanitary moisture absorbents, etc.) and also solidifies small amounts of alcohol components. It can be used as a domestic oil coagulant, heavy oil solidifying agent, organic waste liquid solidifying agent, etc., as well as a flexible material containing a large amount of water, such as biocompatible materials, tissue / cell culture matrices, proteins and nucleic acids, etc. Applicable to biomaterial separation agents.
• Example 1 Applicable to biomaterial separation agents.
• a gelling agent according to the present invention was prepared and collected in water.
• EF-TEM transmission electron microscope with energy filter
• NMR transmission electron microscope with energy filter
• the residue was purified by silica gel / column chromatography using a mixed solvent of tetrahide / furan / chloroform (1/1, by volume) as eluent to give p-aminophenyl ⁇ - ⁇ -Dalcoviranoside was obtained.
• Dodecanoinoleaminophenyl-1 -D-darcoviranoside and dodecanoylaminophenil J3 -D-galactopyranoside (lmg each) obtained in the above example were weighed into a test tube, respectively, and the solution was added to water. A mixed solvent of (900 mg) and methanol (100 mg) was added. Heated for complete dissolution. Then, it was cooled slowly and left at room temperature for about 2 to 5 hours to obtain a hydrated gel that did not lose its shape even when it was inverted.
• Solvents include water (including trace amounts of methanol and ethanol), methanol, ethanol, 1-butano, t-butano, tetrahydrofuran, chloropho / rem, Dichloromethane, n- hexane, ethyl acetate, dimethylformamide, and dimethylsulfoxide were used.
• a solvent of the Rere Zureka in two test tubes of the gelling agent is sealed prepared in Example, 0.1 the concentration of the gelling agent from 1 to 3.0 for a weight 0/0 Mix and heat the mixture until the solids dissolve. The resulting solution was cooled to 25 ° C over 1 hour. The gelling agent and solvent are placed in a septum-capped test tube and heated in an oil bath until the solids dissolve. Cool the solution to 25 ° C.
• gelling agent of the present invention gels water containing a small amount of alcohol (about 1% by weight, that is, 50,000 or more water molecules per one molecule of the gelling agent) at a concentration of 0.1% by weight or less. What has turned out to be very interesting. These results indicate that the gelling agent of the present invention is an amphoteric gelling agent that functions in both water and organic solvents.
• FIG. 1 and FIG. 3 are typical photographs of an aqueous gel by the gelling agent of the present invention. These photographs reveal that this genorizing agent forms a three-dimensional network consisting of wrinkled fibers with a diameter of 20-500 nm. Judging from the SEM photograph (Fig. 3), it can be seen that some ribbon-like structures are twisted and have a left-handed spiral.
• the inventors obtained information on the molecular packing mode of the gelling agent molecule in the orderly gel from the X-ray diffraction of this xerogel.
• the diffraction pattern of the xerogel of the present invention shows a periodic diffraction peak (FIG. 5), which indicates that the xerogel is actually assembled in a layered structure.
• the distance (d) between the aggregates obtained by the XRD method is about 2.90 nm, 1.46 nm and 0.97 nm, which is almost exactly the ratio of 1: 12: 1Z3. It is shorter than twice the molecular length (2.45 nm according to the CPK molecular model) and longer than one molecule.
• aqueous gel force S of the present invention has a finger-like bilayer structure having a molecular film corresponding to the (100) plane with a thickness of 2.90 nm (No. 7).
• the wide-angle X-ray diagram of the aqueous gel of the present invention shows a series of sharp reflection peaks, which indicate that the long-chain alkyl groups have regular layered densities due to finger-like hydrophobic interactions. Indicate a hypothetical view of forming a fill. This is the first example of the formation of a neat bilayer aqueous gel. From the results of XRD, FT-NMR and FT-IR, it was found that the aqueous gel of the present invention was stabilized by a combination of hydrogen bonding, ⁇ - ⁇ interaction and hydrophobic force.

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• 2001
  • 2001-08-07 JP JP2001239014A patent/JP4164247B2/ja not_active Expired - Lifetime
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