CN105032278A - Chitosan fatty acid supramolecular polymer biosurfactant and preparation method thereof - Google Patents
Chitosan fatty acid supramolecular polymer biosurfactant and preparation method thereof Download PDFInfo
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- CN105032278A CN105032278A CN201510339028.2A CN201510339028A CN105032278A CN 105032278 A CN105032278 A CN 105032278A CN 201510339028 A CN201510339028 A CN 201510339028A CN 105032278 A CN105032278 A CN 105032278A
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Abstract
The invention provides a chitosan fatty acid supramolecular polymer biosurfactant which comprises the following raw material components according to a certain ratio each time after 1000 mL of water is added: 10-50 grams of chitosan, 10-25 mL of acetic acid, 10-40 mL of hydrogen peroxide with a mass concentration of 30%, 50-200 grams of fatty acid and 20-100 grams of alkali. The chitosan fatty acid supramolecular polymer biosurfactant can be applied to preparation of a polymer with the macromolecular polysaccharide property according to the fundamental principles of supramolecular chemistry and the supramolecular self-assembly technology, can serve as a solution thickener, has high bacteriostatic activity and biological degradability, and is a natural and environment-friendly biosurfactant.
Description
Technical field
The invention belongs to macromolecule polysaccharide biosurfactant field, be specifically related to a kind of biosurfactant, particularly a kind of shitosan aliphatic acid supermolecule polymer biosurfactant.
Background technology
Surfactant is widely used in daily life, industrial or agricultural and high-technology field, is current most important commercial auxiliaries.Most of surfactant is all take petrochemicals as Material synthesis, in production and use procedure, usually can bring serious problem of environmental pollution.Along with the enhancing of people's environmental consciousness, manyly not degrade, the use of difficult degradation or the long surfactant of degradation cycle is restricted.So biosurfactant arose at the historic moment in 20 century 70 later stages, become the new problem grown up in international bio engineering field.Biosurfactant not only has excellent chemical property, but also it is nontoxic to human body, livestock, to the environmental nonpollution that the mankind depend on for existence, can be biodegradable very soon, simultaneously its production process be a depollution of environment, twice laid, the process that turns waste into wealth, which results in the strong interest of people to biosurfactant, make to develop the important directions that biosurfactant becomes green surfactant development.
Biosurfactant be utilize enzyme or microorganism etc. to be obtained from microorganism, plant and animal by the biotechnology such as living things catalysis and biosynthesis integrate hydrophilic and the natural surfactant with high surface of hydrophobic group structure.Biosurfactant is the up-and-coming youngster in surfactant families, compare with general chemical surfactant, except there is features such as significantly reducing surface tension, stable emulsion, lower critical micelle concentration, also nontoxic or low toxicity, good selective, selectivity and biocompatibility, structure diversity, there is pharmacological action and the immunologic functions such as antibacterial, antiviral and antitumor, biodegradable, environmentally friendly, can be produced by industrial waste, be beneficial to the characteristics such as environmental improvement.
Shitosan is the family member of macromolecule polysaccharide, is natural products chitin deacetylation material, has multiple good physicochemical property and outstanding biological function.Research or industrialization product are chitose graft copolymers both at home and abroad at present, prepared by organic synthesis or enzymatic synthesis method, as (model metals and stones such as CMCs, Sui Weiping, Chen Guohua etc. the fabrication & properties [J] of the novel chitin derivativ of aminosugars surfactant-class. daily chemical industry, 2006,36 (3): 171-3.).
However, mostly there is common shortcoming in the preparation of existing chitosan surfactant: organic synthesis complicated component, and impurity is difficult to remove, and residual treatment cost is higher, and safety in utilization is under suspicion; Enzymatic synthesis production process is complicated, production cost is too high, be difficult to large-scale industrial production (production of biosurfactant and application, Han Shuanyan, Ren Changqiong, Lin Ying. the production of biosurfactant and application [J]. Chinese engineering science .2009,11 (4): 26-30)).
Summary of the invention
For the technical problem that will solve above, the object of this invention is to provide a kind of natural green, modify, have the shitosan aliphatic acid supermolecule polymer biosurfactant of bacteriostasis property without any need for chemistry or biology.
Another object of the present invention is to provide the preparation method of above-mentioned biosurfactant.
Another object of the present invention is to provide the purposes of above-mentioned biosurfactant.
Therefore, the invention provides a kind of shitosan aliphatic acid supermolecule polymer biosurfactant, each raw material components and ratio as follows: often add 1000mL water, shitosan is 10 ~ 50 grams, acetic acid is 10 ~ 25mL, mass concentration be 30% hydrogen peroxide be 10 ~ 40mL, aliphatic acid is 50 ~ 200 grams, and alkali is 20 ~ 100 grams.
Shitosan aliphatic acid supermolecule polymer chemical structure of general formula of the present invention is as follows:
Wherein: R=-C
11h
23,-C
13h
27,-C
15h
31,-C
17h
35,-C
17h
33,-C
17h
31,-C
17h
29; 1≤n < 100.
Chemical equation is as follows:
Preferably, described alkali includes but not limited to as NaOH, sodium carbonate, sodium acid carbonate or wherein multiple arbitrarily mixing.
Preferably, described aliphatic acid includes but not limited to as laurate, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, leukotrienes or wherein multiple arbitrarily mixing.Shitosan aliphatic acid supermolecule polymer obtained thus includes but not limited to respectively as shitosan laurate fat, shitosan myristic acid fat, shitosan palmitic acid lipid, shitosan stearate, shitosan olein, shitosan linoleic acid fat, shitosan leukotrienes fat.
Described aliphatic acid most preferably is oleic acid.Shitosan aliphatic acid supermolecule polymer obtained thus is shitosan oleic acid supermolecule polymer.
Preferably, shitosan of the present invention refers to the product obtained through deacetylation from chitin, deacetylation>=90%, and its chemical general formula is: (C
6h
11nO
4) n, 50 < n < 100.
Preferably, shitosan of the present invention can be low-molecular weight chitoglycan or Glucosamine.
Wherein, described low-molecular weight chitoglycan refers to the shitosan utilizing the methods such as acid hydrolysis, oxidative degradation and enzymolysis to prepare, and its chemical general formula is: (C
6h
11nO
4) n, 10 < n < 50.
Described Glucosamine refers to that shitosan is through the unimolecule shitosan prepared by the methods such as acid hydrolysis, oxidative degradation and enzymolysis; Its molecular formula is: C
6h
13nO
5.
Present invention also offers the preparation method of above-mentioned shitosan aliphatic acid supermolecule polymer biosurfactant, its step is as follows:
(1) acetic acid and water are mixed with acetic acid aqueous solution;
(2) shitosan is added in acetic acid aqueous solution, stirring and dissolving, degrade;
(3) hydrogen peroxide is added, stirring and dissolving;
(4) aliphatic acid is added;
(5) alkali is added;
(6) adding suitable quantity of water to solid content is 20% (weight), stirs and evenly mixs, spraying dry, obtains powdery product.
Preferably, in above-mentioned preparation method, the concentration of described acetic acid aqueous solution is 1 ~ 2.5g/mL.
Preferably, in above-mentioned preparation method, the temperature of carrying out degrading in described step (1) is 60 DEG C ~ 100 DEG C, is more preferably 60 DEG C.
Preferably, in above-mentioned preparation method, the time of carrying out degrading in described step (1) is 6 ~ 10 hours, is more preferably 6 hours.
Preferably, in above-mentioned preparation method, in described step (2), the time of stirring and dissolving is 4 ~ 8 hours, is more preferably 6 hours.
Preferably, in above-mentioned preparation method, the inlet temperature in baking temperature is 100 DEG C, and outlet temperature is 70 DEG C ~ 100 DEG C, is more preferably 80 DEG C.
Present invention also offers the purposes of above-mentioned shitosan aliphatic acid supermolecule polymer biosurfactant as surfactant, bacteriostatic agent.
After testing, the physical and chemical index of shitosan aliphatic acid supermolecule polymer biosurfactant of the present invention divides
Not as follows:
1) fusing point: 165.2 ~ 186.4 DEG C;
2) moisture: 0.25 ~ 0.50%
3) pH value: 7.36 ~ 9.37
4) critical micelle concentration: 55 ~ 65mgL
-1
5) surface tension: 25.8 ~ 27.9mNm
-1
6) HLB value: 8.9 ~ 9.3
7) emulsifying ability: 52.1 ~ 58.4%
8) wetting power: 5.21 ~ 6.73s
9) minimal inhibitory concentration: 9.50 ~ 11.3mgL
-1
Visible, the general principle of the shitosan aliphatic acid supermolecule polymer application supramolecular chemistry prepared by the present invention, adopts Supramolecular self assembly technology, and preparation has the polymer of macromolecule polysaccharide characteristic, can be used as the thickener of solution, relative viscosity value 200-500mPas; Also there is good bacteriostatic activity.In addition, test result shows, the biological degradability of the shitosan aliphatic acid supermolecule polymer biosurfactant prepared by the present invention is 3 days > 90%, is a kind of biosurfactant of natural green.
Accompanying drawing explanation
Fig. 1 is the infrared spectrogram of shitosan aliphatic acid supermolecule polymer biosurfactant of the present invention.
Detailed description of the invention
Below in conjunction with specific embodiments and the drawings, technical scheme of the present invention is described in further detail, but protection scope of the present invention is not limited to following examples.
In following examples and whole raw material used in the present invention all can buy via commercial channel and obtain, as without particularly pointing out, all be at least chemical pure.
Shitosan of the present invention refers to the product obtained through deacetylation from chitin, deacetylation>=90%, and its chemical general formula is: (C
6h
11nO
4) n, 50 < n < 100.Preferably, shitosan of the present invention comprises low-molecular weight chitoglycan and Glucosamine.Wherein, described low-molecular weight chitoglycan refers to the shitosan utilizing the methods such as acid hydrolysis, oxidative degradation and enzymolysis to prepare, and its chemical general formula is: (C
6h
11nO
4) n, 10 < n < 50.Described Glucosamine refers to that shitosan is through the unimolecule shitosan prepared by the methods such as acid hydrolysis, oxidative degradation and enzymolysis; Its molecular formula is: C
6h
13nO
5.
Embodiment 1
Measure 10mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 10g stirring and dissolving 6h, add 30% hydrogen peroxide 10mL stirring and dissolving 6h, add laurate powder 50g, sodium acid carbonate 20g, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 70 DEG C, spraying dry is to powdery product.
Embodiment 2
Measure 20mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 40g stirring and dissolving 6h, add 30% hydrogen peroxide 20mL stirring and dissolving 6h, add laurate powder 100g, sodium acid carbonate 50g, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 80 DEG C, spraying dry is to powdery product.
Embodiment 3
Measure 25mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 50g stirring and dissolving 6h, add 30% hydrogen peroxide 40mL stirring and dissolving 10h, add laurate powder 200g, sodium acid carbonate 100g, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 100 DEG C, spraying dry is to powdery product.
Embodiment 4
Measure 10mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 10g stirring and dissolving 6h, add 30% hydrogen peroxide 10mL stirring and dissolving 6h, myristic acid powder 50g, NaOH 20g is added at 70 DEG C, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 70 DEG C, spraying dry is to powdery product.
Embodiment 5
Measure 20mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 40g stirring and dissolving 6h, add 30% hydrogen peroxide 20mL stirring and dissolving 6h, myristic acid powder 100g, NaOH 50g is added at 70 DEG C, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 80 DEG C, spraying dry is to powdery product.
Embodiment 6
Measure 25mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 50g stirring and dissolving 6h, add 30% hydrogen peroxide 40mL stirring and dissolving 10h, myristic acid powder 200g, NaOH 100g is added at 70 DEG C, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 100 DEG C, spraying dry is to powdery product.
Embodiment 7
Measure 10mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 10g stirring and dissolving 6h, add 30% hydrogen peroxide 10mL stirring and dissolving 6h, palmitic acid powder 50g, sodium carbonate 20g is added at 80 DEG C, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 70 DEG C, spraying dry is to powdery product.
Embodiment 8
Measure 20mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 40g stirring and dissolving 6h, add 30% hydrogen peroxide 20mL stirring and dissolving 6h, palmitic acid powder 100g, sodium carbonate 50g is added at 80 DEG C, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 80 DEG C, spraying dry is to powdery product.
Embodiment 9
Measure 25mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 50g stirring and dissolving 6h, add 30% hydrogen peroxide 40mL stirring and dissolving 10h, palmitic acid powder 200g, sodium carbonate 100g is added at 80 DEG C, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 100 DEG C, spraying dry is to powdery product.
Embodiment 10
Measure 10mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 10g stirring and dissolving 6h, add 30% hydrogen peroxide 10mL stirring and dissolving 6h, stearic acid powder 50g, sodium carbonate 20g is added at 90 DEG C, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 70 DEG C, spraying dry is to powdery product.
Embodiment 11
Measure 20mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 40g stirring and dissolving 6h, add 30% hydrogen peroxide 20mL stirring and dissolving 6h, stearic acid powder 100g, sodium carbonate 50g is added at 90 DEG C, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 80 DEG C, spraying dry is to powdery product.
Embodiment 12
Measure 25mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 50g stirring and dissolving 6h, add 30% hydrogen peroxide 40mL stirring and dissolving 10h, stearic acid powder 200g, sodium carbonate 100g is added at 90 DEG C, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 100 DEG C, spraying dry is to powdery product.
Embodiment 13
Measure 10mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 10g stirring and dissolving 6h, add 30% hydrogen peroxide 10mL stirring and dissolving 6h, oleic acid 50g, sodium acid carbonate 20g is added under room temperature, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 70 DEG C, spraying dry is to powdery product.
Embodiment 14
Measure 20mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 40g stirring and dissolving 6h, add 30% hydrogen peroxide 20mL stirring and dissolving 6h, oleic acid 100g, sodium acid carbonate 50g is added under room temperature, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 80 DEG C, spraying dry is to powdery product.
Embodiment 15
Measure 25mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 50g stirring and dissolving 6h, add 30% hydrogen peroxide 40mL stirring and dissolving 10h, oleic acid 200g, sodium acid carbonate 100g is added under room temperature, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 100 DEG C, spraying dry is to powdery product.
Embodiment 16
Measure 10mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 10g stirring and dissolving 6h, add 30% hydrogen peroxide 10mL stirring and dissolving 6h, linoleic acid 50g, sodium carbonate 20g is added under room temperature, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 70 DEG C, spraying dry is to powdery product.
Embodiment 17
Measure 20mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 40g stirring and dissolving 6h, add 30% hydrogen peroxide 20mL stirring and dissolving 6h, linoleic acid 100g, sodium carbonate 50g is added under room temperature, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 80 DEG C, spraying dry is to powdery product.
Embodiment 18
Measure 25mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 50g stirring and dissolving 6h, add 30% hydrogen peroxide 40mL stirring and dissolving 10h, linoleic acid 200g, sodium carbonate 100g is added under room temperature, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 100 DEG C, spraying dry is to powdery product.
Embodiment 19
Measure 10mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 10g stirring and dissolving 6h, add 30% hydrogen peroxide 10mL stirring and dissolving 6h, leukotrienes 50g, sodium acid carbonate 20g is added under room temperature, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 70 DEG C, spraying dry is to powdery product.
Embodiment 20
Measure 20mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 40g stirring and dissolving 6h, add 30% hydrogen peroxide 20mL stirring and dissolving 6h, leukotrienes 100g, sodium acid carbonate 50g is added under room temperature, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 80 DEG C, spraying dry is to powdery product.
Embodiment 21
Measure 25mL acetic acid add 1000mL pure water and be heated to 60 DEG C, add shitosan 50g stirring and dissolving 6h, add 30% hydrogen peroxide 40mL stirring and dissolving 10h, leukotrienes 200g, sodium acid carbonate 100g is added under room temperature, add water to solid content 20%, stir and evenly mix, regulate inlet temperature 100 DEG C, outlet temperature 100 DEG C, spraying dry is to powdery product.
After testing, every physical and chemical index of the shitosan aliphatic acid supermolecule polymer biosurfactant of the embodiment of the present invention 1 ~ 21 is as follows:
1) fusing point: 165.2-186.4 DEG C;
2) moisture: 0.25-0.50%
3) pH value: 7.36-9.37
4) critical micelle concentration: 55 ~ 65mgL
-1
5) surface tension: 25.8-27.9mNm
-1
6) HLB value: 8.9-9.3
7) emulsifying ability: 52.1-58.4%
8) wetting power: 5.21-6.73s
9) minimal inhibitory concentration: 9.50-11.3mgL
-1
As can be seen here, the shitosan aliphatic acid supermolecule polymer prepared by the embodiment of the present invention 1 ~ 21 has macromolecule polysaccharide characteristic, can be used as the thickener of solution, relative viscosity value 200-500mPas; Also there is good bacteriostatic activity.In addition, test result shows, the biological degradability of the shitosan aliphatic acid supermolecule polymer biosurfactant prepared by the present invention is 3 days > 90%, is a kind of biosurfactant of natural green.
Fig. 1 is the FTIR spectrum figure of shitosan aliphatic acid supermolecule polymer of the present invention.In this FTIR spectrum:
3439cm
-1the multi-absorption peak that-OH stretching vibration of-hydrogen bond association is overlapping and broadening with-NH stretching band; During vibration, the change of dipole moment strengthens, thus absorption intensity increase (Bai Ping Lian, Wei Yu, Wang Haitao etc. with the bonding pattern [J] of infrared spectrum technology research hydrogen bond. chemistry circular .2013,76 (2): 167-70.).
3009cm
-1-unsaturated olefin C-H stretching vibration absworption peak;
2851cm
-1-saturated hydrocarbons C-H stretching vibration absworption peak;
1563cm
-1-aliphatic acid ammonia salt ion antisymmetric stretching vibration absworption peak is the characteristic absorption peak of shitosan aliphatic acid supermolecule polymer.
Analyzed by FTIR spectrum, illustrate in shitosan aliphatic acid supermolecule polymer not to be simple mixing between shitosan and aliphatic acid, but there is multiple interaction, as ionic bond, hydrogen bond, Coulomb force etc., and this effect only when generating solid polymer, just obviously obtains reinforcement.
Claims (10)
1. a shitosan aliphatic acid supermolecule polymer biosurfactant, each raw material components and ratio as follows: often add 1000mL water, shitosan is 10 ~ 50 grams, acetic acid is 10 ~ 25mL, mass concentration be 30% hydrogen peroxide be 10 ~ 40mL, aliphatic acid is 50 ~ 200 grams, and alkali is 20 ~ 100 grams.
2. shitosan aliphatic acid supermolecule polymer biosurfactant according to claim 1, is characterized in that, described alkali is any one in NaOH, sodium carbonate, sodium acid carbonate.
3. shitosan aliphatic acid supermolecule polymer biosurfactant according to claim 1, is characterized in that, described aliphatic acid is any one in laurate, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, leukotrienes.
4. shitosan aliphatic acid supermolecule polymer biosurfactant according to claim 3, it is characterized in that, described aliphatic acid is oleic acid.
5. shitosan aliphatic acid supermolecule polymer biosurfactant according to claim 1, it is characterized in that, described shitosan is low-molecular weight chitoglycan or Glucosamine.
6. shitosan aliphatic acid supermolecule polymer biosurfactant according to claim 5, it is characterized in that, the chemical general formula of described low-molecular weight chitoglycan is: (C
6h
11nO
4) n, 10 < n < 50.
7. the preparation method of shitosan aliphatic acid supermolecule polymer biosurfactant according to claim 1, its step is as follows:
(1) acetic acid and water are mixed with acetic acid aqueous solution;
(2) shitosan is added in acetic acid aqueous solution, stirring and dissolving, degrade;
(3) hydrogen peroxide is added, stirring and dissolving;
(4) aliphatic acid is added;
(5) alkali is added;
(6) adding suitable quantity of water to solid content is 20%, stirs and evenly mixs, spraying dry, obtains powdery product.
8. method according to claim 7, is characterized in that, the concentration of described acetic acid aqueous solution is 1 ~ 2.5g/mL.
9. method according to claim 7, is characterized in that, the temperature of carrying out degrading in described step (1) is 60 DEG C ~ 100 DEG C.
10. shitosan aliphatic acid supermolecule polymer biosurfactant according to claim 1 is as the purposes of surfactant, bacteriostatic agent.
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| CN105533108A (en) * | 2016-01-06 | 2016-05-04 | 广州拜恩生物技术有限公司 | Liquid gum and preparing method thereof |
| CN107056955A (en) * | 2017-05-26 | 2017-08-18 | 厦门大学 | A kind of exploitation for the synthesis and green surfactant for intending chitosan soap |
| CN107712587A (en) * | 2017-10-17 | 2018-02-23 | 广州润虹医药科技股份有限公司 | A kind of anti-oxidant anti-aging nutrient powder and preparation method thereof |
| CN111108993A (en) * | 2019-12-25 | 2020-05-08 | 南京绿宙薄壳山核桃科技有限公司 | Selenium-rich fertilizer for apocarya, preparation method and application thereof, and selenium-rich cultivation method for apocarya |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105533108A (en) * | 2016-01-06 | 2016-05-04 | 广州拜恩生物技术有限公司 | Liquid gum and preparing method thereof |
| CN107056955A (en) * | 2017-05-26 | 2017-08-18 | 厦门大学 | A kind of exploitation for the synthesis and green surfactant for intending chitosan soap |
| CN107056955B (en) * | 2017-05-26 | 2020-12-25 | 厦门大学 | Synthesis of pseudo-chitosan-fatty acid salt and development of green surfactant |
| CN107712587A (en) * | 2017-10-17 | 2018-02-23 | 广州润虹医药科技股份有限公司 | A kind of anti-oxidant anti-aging nutrient powder and preparation method thereof |
| CN111108993A (en) * | 2019-12-25 | 2020-05-08 | 南京绿宙薄壳山核桃科技有限公司 | Selenium-rich fertilizer for apocarya, preparation method and application thereof, and selenium-rich cultivation method for apocarya |
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|---|---|
| CN105032278B (en) | 2019-09-03 |
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