CN112169713A - N-alkyl lactosamine surfactant micromolecule alcogel and preparation method thereof - Google Patents

N-alkyl lactosamine surfactant micromolecule alcogel and preparation method thereof Download PDF

Info

Publication number
CN112169713A
CN112169713A CN202010940949.5A CN202010940949A CN112169713A CN 112169713 A CN112169713 A CN 112169713A CN 202010940949 A CN202010940949 A CN 202010940949A CN 112169713 A CN112169713 A CN 112169713A
Authority
CN
China
Prior art keywords
lactosamine
alkyl
gel
alcogel
ethanol
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.)
Withdrawn
Application number
CN202010940949.5A
Other languages
Chinese (zh)
Inventor
葛新
潘佳佳
刘学民
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.)
Jiangnan University
Original Assignee
Jiangnan University
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
Application filed by Jiangnan University filed Critical Jiangnan University
Priority to CN202010940949.5A priority Critical patent/CN112169713A/en
Publication of CN112169713A publication Critical patent/CN112169713A/en
Withdrawn legal-status Critical Current

Links

Images

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/0052—Preparation of gels
    • B01J13/0065—Preparation of gels containing an organic phase
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/325—Amines
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions

Abstract

The invention discloses N-alkyl lactosamine surfactant micro-molecular alcogel and a preparation method thereof, belonging to the field of fine chemical engineering. The invention utilizes N-alkyl lactosamine to disperse in alcoholic solution, heat to dissolve, then stand at 0-35 ℃ to form N-alkyl lactosamine micromolecule alcoholic gel. The small molecular alcohol gel has simple preparation process, does not need to adjust pH in the preparation process, can be preserved for a long time, has good biocompatibility, environmental compatibility and raw material reproducibility, has low toxicity, and can be widely applied to the fields of daily chemical products, environmental engineering, food, biomedicine and the like.

Description

N-alkyl lactosamine surfactant micromolecule alcogel and preparation method thereof
Technical Field
The invention belongs to the field of fine chemical engineering, and particularly relates to N-alkyl lactosamine surfactant micromolecule alcogel and a preparation method thereof.
Background
Over the last few years, there has been increasing interest in the synthesis and performance of new surfactants based on natural products. The reason for selecting natural raw materials is: renewable substrates (starting materials) -derived from a continuous ecological cycle; the substrate has low cost and is usually easily obtained in nature, such as sucrose, lactose and glucose; starting materials of low toxicity and high biodegradability come from nature and therefore microorganisms suitable for their degradation can be found in the environment; the various product surfactants have a very wide variety of structures, i.e., sugars (monosaccharides, disaccharides, etc.) can be linked to any of their hydroxyl groups by different types or linkages. Compared with other surfactants, the lactamine surfactant has many outstanding advantages, such as high surface activity up to critical micelle concentration; the foam is easy to dissolve in aqueous solution, the foam is rich, fine and stable, and the hard water resistance and the grease resistance of the foam are obviously improved after the foam is compounded with an anionic surfactant for use; strong detergency, small irritation, and no obvious damage to skin and hair; the product is stable and does not generate precipitate after being placed for a long time; the biodegradation is fast and complete.
The gel is a special colloid dispersion system in which colloid particles or organic molecules are connected with each other under certain conditions to form a space network structure, and the gaps in the network structure are filled with solvent molecules (dispersion medium, liquid or gas). The gel shows solid-like rheological property on rheology, and has extremely high viscosity and high elasticity. In appearance, the gel is in a solid-like state and has the characteristic of no flowing after being inverted, which is also a basic condition for judging whether a sample is gel. Since the first report in 1860, the gel has been widely applied in the fields of daily chemical products, environmental engineering, biomedicine and the like due to the excellent biocompatibility and the multi-layer and multi-scale ultrastructure. The micromolecule gel has small size and few functional groups, is relatively easy to research intermolecular interaction and assemble, has simple and easily-modified synthetic process, and has the advantages of biocompatibility, low toxicity, easy degradation and the like. And the micromolecule gel has the characteristics of quick response to external environment stimulation, thermal reversibility, thixotropy, self-repairing, self-healing and the like. The field of small molecule gels has therefore attracted considerable interest to scientists.
Disclosure of Invention
At present, gels utilizing lactosamine are all multi-component systems constructed to obtain gel products, and glucosamine can be self-constructed to obtain the gels under certain environments. The invention aims to provide a preparation method of a micromolecule alcogel based on lactosamine nonionic surfactant, the raw materials used by the micromolecule alcogel are all renewable resources, the biodegradability is strong, the performance is mild, the irritation to skin is small, the micromolecule alcogel can be compounded with other surfactants for use, and the micromolecule alcogel can be widely applied to detergents and cosmetics.
The technical scheme of the invention is as follows:
the invention provides a method for preparing N-alkyl lactosamine small molecule alcogel, the structural formula of said N-alkyl lactosamine is as follows:
Figure BDA0002673608510000021
wherein R is C12-C16Alkyl radical
The method comprises the steps of dissolving N-alkyl lactosamine shown in formula (1) in ethanol solution, and standing to form N-alkyl lactosamine alcoholic gel.
In one embodiment of the invention, R is selected from: n-dodecyl, n-tetradecyl, n-hexadecyl.
In one embodiment of the present invention, the alcohol solution refers to an aqueous solution of alcohol with a mass fraction of 50 wt% to 100 wt%. Further preferably 80 wt% to 100 wt%.
In one embodiment of the invention the mass fraction of N-alkyl lactosamine relative to alcoholic solution is between 0.5 wt% and 90 wt%. That is, the gel concentration of the formed N-alkyl lactosamine alcohol gel ranges from 0.5 wt% to 90 wt%.
In one embodiment of the invention the mass fraction of N-alkyl lactosamine relative to alcoholic solution is preferably 0.5 wt% -2 wt%.
In one embodiment of the invention, the dissolution is performed by adding N-alkyl lactosamine to the alcohol solution and heating to 60-120 ℃.
In one embodiment of the invention, the standing is at 0-35 ℃ for 2-10 min.
In one embodiment of the present invention, a lactosamine surfactant small molecule alcogel is prepared by the following steps:
to the white crystals of N-alkyl lactosamine was added different proportions of alcoholic solution and heated until the white crystals dissolved. Then standing at 0-35 ℃ to form N-alkyl lactose amine alcohol gel; the gel concentration range of the N-alkyl lactose amine alcohol gel is 0.5 wt% -90 wt%.
The invention also discloses an N-alkyl lactose amine alcohol gel prepared by the method.
The invention also applies the N-alkyl lactosamine ethanol gel prepared above to the biomedical fields of daily chemical articles, environmental engineering, food, non-disease diagnosis and treatment methods.
The invention has the beneficial effects that:
the N-alkyl lactosamine ethanol gel prepared by the invention has the advantages of cheap and easily obtained raw materials, simple synthesis steps, no need of PH regulation, long-term preservation, good application performance, biocompatibility, environmental compatibility and raw material reproducibility, small irritation to skin and mucosa, soft function to fabrics and hair, and the like, and is widely applied to the fields of daily chemical products, environmental engineering, food, biomedicine and the like.
Drawings
FIG. 1 is a macroscopic picture of the 1.67 wt% N-N-dodecyllactosamine ethanol gel obtained in example 1.
FIG. 2 is a macroscopic picture of the 2.5 wt% N-N-dodecyllactosamine ethanol gel obtained in example 2.
FIG. 3 is a macroscopic picture of the 2.5 wt% N-tetradecyl lactosamine ethanol gel obtained in example 3.
FIG. 4 is a macroscopic picture of the 1.25 wt% N-tetradecyl lactosamine ethanol gel obtained in example 4.
FIG. 5 is a macroscopic picture of the 1.25 wt% N-N-hexadecyllactosamine ethanol gel obtained in example 5.
FIG. 6 is a macroscopic picture of the 0.5 wt% N-N-hexadecyllactosamine ethanol gel obtained in example 6.
FIG. 7 macroscopic pictures (from left to right) of 2.5 wt% N-N-dodecyllactosamine ethanol gel, N-N-tetradecyllactosamine ethanol and N-N-hexadecyllactosamine ethanol gel obtained in example 7.
FIG. 8 is a macroscopic picture of N-N-dodecyllactosamine, N-N-tetradecyllactosamine and N-N-hexadecyllactosamine (from left to right) in DMF according to comparative example 1.
FIG. 9 is a macroscopic picture of the ethanol gel of N-N-dodecyllactosamine with a mass fraction of 2.5 wt% formed in isopropanol, isobutanol (from left to right) in example 10.
Detailed Description
The present invention will be further described with reference to the following examples. It is to be understood that the following examples are illustrative only and are not intended to limit the scope of the invention, which is to be given the full breadth of the appended claims and any and all insubstantial modifications and variations of those skilled in the art which are within the scope of the following claims.
The sources of N-N-dodecyl lactosamine, N-N-tetradecyl lactosamine, N-N-hexadecyl lactosamine related to this invention are as follows:
lactose monohydrate (18mmol, 6.486g) was dissolved in 60mL of ultrapure water and N-alkylamine (30mmol) was dissolved in 100mL of isopropanol. The two solutions were mixed and stirred at room temperature for 24 hours and then transferred to a water bath at 60 ℃ for 30 minutes. And (3) carrying out suction filtration on the mixture to remove the solvent, washing a filter cake with ethanol for three times, recrystallizing in ethanol, carrying out suction filtration, and then carrying out rotary evaporation to remove the ethanol to obtain solid powder.
The structural characterization data for the 3N-alkyl lactosamines involved are as follows:
N-N-dodecyl lactosamine: white solid m.p.131.6 deg.C-131.8℃.1H NMR(400MHz,MeOD)4.38(d,J＝3.2Hz,1H),3.89–3.77(m,5H),3.72(d,J＝7.6,3.2Hz,1H),3.62–3.48(m,5H),3.40–3.35(m,1H),3.15(t,J＝6.0Hz,1H),2.91(m,1H),2.65(m,1H),1.58–1.46(m,2H),1.33(d,J＝12.8Hz,18H),0.92(t,J＝4.8Hz,3H).13C NMR(100MHz,MeOD)103.72,90.37,79.57,76.10,75.87,75.69,73.45,73.25,71.19,68.91,61.10,60.75,31.67,29.65,29.31(d,J＝7.0Hz),29.07,27.00,22.33,13.02.
N-N-tetradecyl lactosamine: light yellow solid, m.p. 109.5-110.4 deg.C.1H NMR(400MHz,DMSO)5.12(s,1H),4.80(s,1H),4.64(s,2H),4.49(d,J＝29.6Hz,2H),4.19(d,J＝12.4,7.6Hz,1H),3.76–3.15(m,14H),2.93(t,J＝8.4Hz,1H),2.77(d,J＝11.2,7.2Hz,1H),1.37(d,J＝6.4Hz,2H),1.24(s,22H),0.86(t,J＝6.4Hz,3H).13C NMR(100MHz,MeOD)103.72,90.38,79.58,76.10,75.87,75.69,73.45,73.25,71.19,68.91,61.10,60.75,40.92,31.67,29.21(d,J＝11.0Hz),29.07,27.01,26.57,22.33,13.02.
N-N-hexadecyllactosamine: light yellow solid, m.p.125.6-126.5 deg.c.1H NMR(400MHz,DMSO)5.12(s,1H),4.80(s,1H),4.64(s,2H),4.49(d,J＝25.6Hz,2H),4.19(d,J＝12.4,7.6Hz,1H),3.76–3.15(m,14H),2.93(t,J＝8.4Hz,1H),2.77(d,J＝11.2,7.2Hz,1H),1.37(m,2H),1.24(s,22H),0.86(t,J＝6.4Hz,3H).13C NMR(100MHz,MeOD)103.71,90.37,79.56,76.10,75.86,75.68,73.44,73.24,71.18,68.91,61.09,60.74,40.66,31.67,29.37,29.06,27.00,26.48,22.33,13.02.
Example 1
The N-N-dodecyl lactosamine ethanol gel of this example was prepared as follows:
0.05g N-n-dodecyllactosamine (formula 1) was dissolved in 3g of ethanol and heated at 110 ℃ until the white crystals dissolved. Then standing at 20 ℃ for 12 minutes to form 1.67 wt% N-N-dodecyllactosamine ethanol gel, which is shown in FIG. 1.
Figure BDA0002673608510000041
Example 2
The N-N-dodecyl lactosamine ethanol gel of this example was prepared as follows:
0.05g N-n-dodecyllactosamine (formula 1) was dissolved in 2g of ethanol and heated at 110 ℃ until the white crystals dissolved. Then standing at 20 ℃ for 10 minutes to form 2.5 wt% N-N-dodecyllactosamine ethanol gel, the gel formed is shown in FIG. 2.
Example 3
The N-N-tetradecyl lactosamine ethanolic gel of this example was prepared as follows:
0.05g N-n-tetradecyl lactosamine (formula 2) was dissolved in 2g of ethanol and heated at 80 ℃ until white crystals were dissolved. Then, the mixture was allowed to stand at 20 ℃ for 7 minutes to form a 2.5 wt% N-tetradecyl lactosamine ethanol gel, which is shown in FIG. 3.
Figure BDA0002673608510000051
Example 4
The N-N-tetradecyl lactosamine ethanolic gel of this example was prepared as follows:
0.05g N-n-tetradecyl lactosamine (formula 2) was dissolved in 4g of ethanol and heated at 80 ℃ until white crystals were dissolved. Then left to stand at 20 ℃ for 9 minutes, a 1.25 wt% N-tetradecyl lactosamine ethanol gel was formed, and the gel formed was as shown in FIG. 4.
Example 5
The N-N-hexadecyllactosamine ethanolic gel of this example was prepared as follows:
0.05g N-n-hexadecyllactosamine (formula 3) was dissolved in 4g of ethanol and heated at 60 ℃ until white crystals were dissolved. Then left to stand at 25 ℃ for 3 minutes to form a 1.25 wt% N-N-hexadecyllactosamine ethanol gel, which is shown in FIG. 5.
Figure BDA0002673608510000052
Example 6
The N-N-hexadecyllactosamine ethanolic gel of this example was prepared as follows:
0.05g N-n-hexadecyllactosamine (formula 3) was dissolved in 10g of ethanol and heated at 70 ℃ until white crystals were dissolved. Then left to stand at 20 ℃ for 5 minutes to form a 0.5 wt% N-N-hexadecyllactosamine ethanolic gel, which is shown in FIG. 6.
Example 7 Alcoholic gel Performance test
Stability: 0.05g N-n-dodecyllactosamine (formula 1), 0.05g N-n-tetradecyllactosamine (formula 2) and 0.05g N-n-hexadecyllactosamine (formula 3) were dissolved in 2g of ethanol respectively, and heated at 100 ℃ until white crystals were dissolved. Then, the mixture was allowed to stand at 25 ℃ for 5 minutes to form a 2.5 wt% N-alkylglucurolactone ethanol gel. The best stability of the N-N-dodecyllactosamine ethanolic gels was obtained by comparison after 24 hours of standing respectively, as shown in FIG. 7. The N-N-dodecyl lactosamine ethanol gel still keeps relatively stable gel-like after being placed for 24 h; both the N-N-tetradecyl lactosamine ethanol gel and the N-N-hexadecyl lactosamine ethanol gel can maintain the stability of the gel for 20h, begin to dissipate after being placed for 20h, and are in the form of solution after being placed for 24 h.
Mechanical strength: the gel strength of the thermal gel was determined according to the method of national standard GB 28304-2012. Analyzing gel strength with gel strength analyzer, wherein the probe is cylindrical and has a flat end with an area of 1cm2. The cross section area of the sample is larger than the area of the probe, the puncture mode and the speed before test are 1mm & s-1The speed during the test is 1mm s-1The speed after the test was 1mm · s-1Obtaining a fracture curve, and calculating the gel strength according to the load-time curve, wherein the gel strength is calculated according to the following formula: w is F/A. Wherein W is the gel strength in g.cm-2(ii) a F is the force of the sharp drop inflection point of the curve when the gel is broken, and the unit gram force (g); a is the area of the plane at the tail end of the probe in cm2. The gel strength of the three alcogels is measured at 800-1300g/cm2The retention rate reaches 85 percentAbove, the gel removal rate is lower than 25%.
Wherein, gel retention: the ratio of the residual mass of the gel to the total gel mass under the external pressure of 0.8MPa-1.3MPa is calculated by the following formula:
Figure BDA0002673608510000061
removal rate of gel: under the external pressure of 0.8MPa-1.3MPa, the ratio of the mass of the solvent removed from the gel to the total gel mass is calculated by the following formula: the removal rate of gel (mass of removed solvent (g)/mass of total gel (g)) was 100%.
Toxicity: after the three kinds of alcohol gel and the cells are co-cultured for 24 hours, the cell survival rate is more than 85 percent by using a lymphocyte proliferation detection method.
Example 8
The concentration of the ethanol solution in the N-alkyl lactosamine ethanol gel of this example was optimized as follows:
0.05g N-n-dodecyllactosamine (formula 1) was dissolved in 2g of 50%, 60%, 70%, 80%, 90% and 100% ethanol solution, respectively, and heated at 110 ℃ until the white crystals were dissolved. Then standing for 5 minutes at 25 ℃ to form 2.5 wt% N-N-dodecyl lactosamine ethanol gel. When 50%, 60% or 70% ethanol solution is used for preparing gel, the obtained alcohol gel can be maintained at gel stability for 16-20h and can be dispersed into solution when placed for 24 h; when 80%, 90% and 100% ethanol solutions were used to prepare the gels, the resulting alcogels remained well gel stable after 24h of standing. The preferred range of concentration of the ethanolic solution for forming the N-N-dodecyllactosamine ethanolic gel is from 80% to 100% by weight, as compared to the rate of gel formation upon cooling and the stability of the gel.
Likewise, the concentration of the ethanol solution in N-N-tetradecyl lactosamine ethanol gel and N-N-hexadecyl lactosamine ethanol gel is preferably also in the range of 80% wt to 100% wt.
Example 9
The difference in stability between the resulting ethanolic gels at different gel concentrations in the N-dodecyllactamide ethanolic gel of this example:
0.05g N-n-dodecyllactosamine (formula 1) was dissolved in 0.5g, 1g, 2g, 5g, 10g and 20g of 100% ethanol solution, respectively, and heated at 110 ℃ until the white crystals were dissolved. Then standing at 25 ℃ to form 10 wt%, 5 wt%, 2.5 wt%, 1 wt%, 0.5 wt% and 0.25 wt% of N-N-dodecyl lactosamine ethanol gel respectively. When 0.25 wt% is added, the obtained alcogel can be placed for 8 hours for gelation stabilization, and a dissipation trend appears after 8 hours; when 0.5 wt% -2 wt% is added, the obtained alcogel can still keep relatively stable gel after being placed for 24 hours; when 2.5 wt% and 5 wt% are added, the obtained alcogel can be stably placed for 20h and 16h respectively. The preferred range of gel stability for ethanol of different mass fractions was found by standing for a stabilization time to be 0.5 wt% to 2 wt%.
Comparative example 1
The case of this example when the ethanol solution was replaced with N, N' -Dimethylformamide (DMF) was as follows:
0.05g N-n-dodecyllactosamine (formula 1), 0.05g N-n-tetradecyllactosamine (formula 3) and 0.05g N-n-hexadecyllactosamine (formula 5) were dissolved in 2g of DMF, respectively, heated at 100 ℃ until white crystals were dissolved, and then left to stand at 25 ℃ without forming a gel, as shown in FIG. 8.
Example 10
The case of replacing ethanol in the N-N-dodecyl lactosamine ethanol gel with isopropanol and isobutanol in this example is as follows:
0.05g N-n-dodecyllactosamine (formula 1) was dissolved in 2g of 100% isopropanol and isobutanol, respectively, and heated at 100 ℃ until the white crystals were dissolved. Then standing at 25 ℃ for 3 minutes to form 2.5 wt% N-N-dodecyllactosamine isopropanol gel and N-N-dodecyllactosamine isobutanol gel, respectively, the gels formed are shown in FIG. 9. The resulting N-N-dodecyllactosamine isopropanol gel may be left to stand for 20 hours for better gel stability, while N-N-dodecyllactosamine isobutanol gel may be left to stand for 18 hours for better gel stability.
The foregoing shows and describes the general principles and features of the present invention, together with the advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are intended to illustrate the principles of the invention, but that various changes and modifications may be made without departing from the spirit and scope of the invention, which is intended to be covered by the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.

Claims (10)

1. A method for the preparation of N-alkyl lactosamine small molecule alcogel characterized in that said N-alkyl lactosamine has the following structural formula:
Figure FDA0002673608500000011
wherein R is C12-C16Alkyl radical
The method is that N-alkyl lactosamine shown in formula (1) is dissolved in alcohol solution and then stands to form N-alkyl lactosamine micromolecule alcogel.
2. The method according to claim 1, wherein the alcohol solution is an aqueous solution of alcohol with a mass fraction of 50 wt% to 100 wt%.
3. The method according to claim 1, wherein the mass fraction of N-alkyl lactosamine relative to alcoholic solution is 0.5 wt% to 90 wt%.
4. The method according to claim 1, wherein the mass fraction of N-alkyl lactosamine relative to alcoholic solution is 0.5% -2% by weight.
5. The method of claim 1, wherein the dissolving is performed by adding N-alkyl lactosamine to the alcohol solution and heating to 60-120 ℃.
6. The method of claim 1, wherein R is selected from the group consisting of: n-dodecyl, n-tetradecyl, n-hexadecyl.
7. The method according to any one of claims 1 to 6, wherein the standing is at 0 to 35 ℃ for 2 to 10 min.
8. An N-alkyl lactosamine small molecule alcogel prepared by the method of any one of claims 1-7.
9. Use of the N-alkyl lactosamine small molecule alcogel of claim 8 in the fields of daily chemicals, environmental engineering, food.
10. Use of the N-alkyl lactosamine small molecule alcogel of claim 8 in the biomedical field of non-disease diagnostic and therapeutic methods.
CN202010940949.5A 2020-09-09 2020-09-09 N-alkyl lactosamine surfactant micromolecule alcogel and preparation method thereof Withdrawn CN112169713A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202010940949.5A CN112169713A (en) 2020-09-09 2020-09-09 N-alkyl lactosamine surfactant micromolecule alcogel and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202010940949.5A CN112169713A (en) 2020-09-09 2020-09-09 N-alkyl lactosamine surfactant micromolecule alcogel and preparation method thereof

Publications (1)

Publication Number Publication Date
CN112169713A true CN112169713A (en) 2021-01-05

Family

ID=73920970

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202010940949.5A Withdrawn CN112169713A (en) 2020-09-09 2020-09-09 N-alkyl lactosamine surfactant micromolecule alcogel and preparation method thereof

Country Status (1)

Country Link
CN (1) CN112169713A (en)

Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1909911A (en) * 2003-10-01 2007-02-07 浩鼎生技公司 Treatment of a condition in a mammal with adminisration of aminosugar and uses thereof
CN101085419A (en) * 2007-06-21 2007-12-12 北京服装学院 Glycosyl quaternary ammonium salt cation surfactant, preparation method and application
CN102614111A (en) * 2012-04-05 2012-08-01 苏州豫源生物医药有限公司 Glucosamine gel and preparation method thereof
CN102942651A (en) * 2012-12-11 2013-02-27 天津工业大学 Galactose-base temperature-sensitive microgel and preparation method thereof
CN103006444A (en) * 2011-09-28 2013-04-03 韩冰 Use of gel material in therapeutic process of dental disease
CN103797050A (en) * 2012-07-27 2014-05-14 宝洁公司 Consumer product compositions comprising organopolysiloxane emulsions
US20140296354A1 (en) * 2013-04-01 2014-10-02 Old Dominion University Research Foundation Synthesis of peptoid-based small molecular gelators from multiple component reactions
CN106413672A (en) * 2013-12-03 2017-02-15 莱雅公司 Composition comprising an aqueous medium
WO2018065450A1 (en) * 2016-10-04 2018-04-12 Aarhus Universitet Flexible and multi-functional coacervates and hydrogel materials
CN108350012A (en) * 2015-08-25 2018-07-31 国立大学法人九州大学 New sugar derivatives gelling agent
CN110023341A (en) * 2016-08-03 2019-07-16 高德美研究及发展公司 The method for being crosslinked glycosaminoglycan
CN110036036A (en) * 2016-08-03 2019-07-19 高德美研究及发展公司 The glycosaminoglycan of dual crosslinking
WO2019175240A1 (en) * 2018-03-13 2019-09-19 Novozymes A/S Microencapsulation using amino sugar oligomers
CN110870881A (en) * 2018-08-30 2020-03-10 强生消费者公司 Topical composition comprising pichia anomala and N-acetylglucosamine
CN111356431A (en) * 2017-11-21 2020-06-30 化工产品开发公司Seppic Self-reversible inverse latex comprising an alkyl polyglycoside as inverse, use thereof as thickener, and cosmetic composition comprising same
CN111545139A (en) * 2020-06-04 2020-08-18 云南中烟工业有限责任公司 Reversible phase-change atomized liquid gel containing glycosyl-amido-aryl-alkyl four-section glycosyl gelling agent and preparation method and application thereof

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1909911A (en) * 2003-10-01 2007-02-07 浩鼎生技公司 Treatment of a condition in a mammal with adminisration of aminosugar and uses thereof
CN101085419A (en) * 2007-06-21 2007-12-12 北京服装学院 Glycosyl quaternary ammonium salt cation surfactant, preparation method and application
CN103006444A (en) * 2011-09-28 2013-04-03 韩冰 Use of gel material in therapeutic process of dental disease
CN102614111A (en) * 2012-04-05 2012-08-01 苏州豫源生物医药有限公司 Glucosamine gel and preparation method thereof
CN103797050A (en) * 2012-07-27 2014-05-14 宝洁公司 Consumer product compositions comprising organopolysiloxane emulsions
CN102942651A (en) * 2012-12-11 2013-02-27 天津工业大学 Galactose-base temperature-sensitive microgel and preparation method thereof
US20140296354A1 (en) * 2013-04-01 2014-10-02 Old Dominion University Research Foundation Synthesis of peptoid-based small molecular gelators from multiple component reactions
CN106413672A (en) * 2013-12-03 2017-02-15 莱雅公司 Composition comprising an aqueous medium
CN108350012A (en) * 2015-08-25 2018-07-31 国立大学法人九州大学 New sugar derivatives gelling agent
CN110036036A (en) * 2016-08-03 2019-07-19 高德美研究及发展公司 The glycosaminoglycan of dual crosslinking
CN110023341A (en) * 2016-08-03 2019-07-16 高德美研究及发展公司 The method for being crosslinked glycosaminoglycan
WO2018065450A1 (en) * 2016-10-04 2018-04-12 Aarhus Universitet Flexible and multi-functional coacervates and hydrogel materials
CN111356431A (en) * 2017-11-21 2020-06-30 化工产品开发公司Seppic Self-reversible inverse latex comprising an alkyl polyglycoside as inverse, use thereof as thickener, and cosmetic composition comprising same
WO2019175240A1 (en) * 2018-03-13 2019-09-19 Novozymes A/S Microencapsulation using amino sugar oligomers
CN110870881A (en) * 2018-08-30 2020-03-10 强生消费者公司 Topical composition comprising pichia anomala and N-acetylglucosamine
CN111545139A (en) * 2020-06-04 2020-08-18 云南中烟工业有限责任公司 Reversible phase-change atomized liquid gel containing glycosyl-amido-aryl-alkyl four-section glycosyl gelling agent and preparation method and application thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
SANTANU BHATTACHARYA, ET AL: "Pronounced Hydrogel Formation by the Self-Assembled Aggregates of N-Alkyl Disaccharide Amphiphiles", 《CHEM. MATER.》 *
SOUGATA DATTA, ET AL.: "Multifarious facets of sugar-derived molecular gels: molecular features, mechanisms of self-assembly and emerging applications", 《CHEM. SOC. REV.》 *

Similar Documents

Publication Publication Date Title
CN105315507B (en) A kind of method for preparing modified graphene chitosan laminated film
RU2428482C2 (en) Method of preparing composition with improved rheological properties (versions) and composition obtained using said methods
Jiang et al. Acid/ethanol induced pectin gelling and its application in emulsion gel
JP2011527900A (en) Bacterial cellulose-containing preparations lacking carboxymethylcellulose components
CN105622780B (en) A kind of homogeneous preparation method of quaternized chitin
CN109260095A (en) A kind of small molecule sodium hyaluronate stoste
Chen et al. Synthesis and properties of alkyl β-D-galactopyranoside
CN103665393A (en) Electrostatic interaction induced micelle preparation method
CN103130675A (en) Industrial production method of high-purity N-lauroyl-L-alanine surfactant
CN105218845B (en) A kind of preparation method of modified graphene polymethyl methacrylate laminated film
CN103834046A (en) Method for preparing natural cellulose containing zein mixture by using alcoholic solvent
CN112169713A (en) N-alkyl lactosamine surfactant micromolecule alcogel and preparation method thereof
Wang et al. Synergistic effect of dual hydrogen-donor deep eutectic solvent for performance improvement of fracturing-oil expulsion fluids
Qiao et al. Structural characterization and emulsifier property of yeast mannoprotein enzymatically prepared with a β-1, 6-glucanase
CN103074130B (en) Preparation method of water-alcohol mixed base micro-emulsified diesel oil
CN109721740A (en) A method of continuously preparing the chitin/chitosan solution of different deacetylations
CN112142805B (en) N-alkylglucosamine small-molecule alcohol gel and preparation method and application thereof
Ali et al. New Y-shaped surfactants from renewable resources
CN111939851A (en) N-alkyl glucamide micromolecule alcohol gel and preparation method and application thereof
CN104496961B (en) The substituted Gluconate of acetal and Preparation method and use
CN106669535B (en) A kind of viscoelastic system of the Gemini surface active agent based on hydroxyl group
CN112138611A (en) N-alkylglucosamine small-molecule hydrogel and preparation method and application thereof
ES2865332T3 (en) Process for preparing compositions comprising alkyl alkyl gulosidouronates, said compositions and their use as a surfactant
JP6222642B2 (en) Emulsifier, emulsion, method for producing emulsifier, and raw material for producing emulsifier
CN112108083A (en) N-alkyl lactosamine surfactant micromolecule hydrogel and preparation method thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WW01 Invention patent application withdrawn after publication

Application publication date: 20210105

WW01 Invention patent application withdrawn after publication