CN1803852A - Method for preparing organic solvent soluble amphiphilic N,N-dilong chain alkyl chitosan - Google Patents
Method for preparing organic solvent soluble amphiphilic N,N-dilong chain alkyl chitosan Download PDFInfo
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- CN1803852A CN1803852A CN 200510022634 CN200510022634A CN1803852A CN 1803852 A CN1803852 A CN 1803852A CN 200510022634 CN200510022634 CN 200510022634 CN 200510022634 A CN200510022634 A CN 200510022634A CN 1803852 A CN1803852 A CN 1803852A
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Abstract
The disclosed preparation method for amphiphilic N, N-double long-chain alkylchitosan in fine chemical industry comprises: preparing Schiff base with aldehyde and chitosan promoted by phase-transfer catalyst; reducing with NaBH4; repeating former process to compose the target. This product can dissolve in organic solvent (chloroform, pyridine and THF) for wide application.
Description
Technical field
The present invention relates to natural polymer-Chemical Modifications of Chitosan, belong to the technical field of fine chemistry industry.Be the amphiphilic N that dissolves in organic solvent specifically, the preparation method of the two alkylated chitosans of N-.
Background technology
Chitosan is a kind of natural polysaccharide, has excellent biological compatibility and biological degradability, and nontoxic, nonirritant, no sensitization, no mutation effect are widely used in fields such as medicine, daily use chemicals, food, environmental protection, weaving and agricultural.In order to give new function of chitosan and the range of application of widening chitosan, it is a kind of effective means that chitosan is carried out chemical modification.Chitosan N-alkylation modification is the more a kind of modification type of research, and the N-alkylated chitosan is the important chitosan derivatives of a class, and it can change the hydrophilic and hydrophobic of chitosan.Relevant synthetic N-alkylation or N, the report of N-alkylated chitosan focuses mostly in adopting short-chain alkyl and halogenated hydrocarbon that chitosan is carried out alkylation modification.With N-alkylation or the N that these methods obtain, the N-alkylated chitosan though have amphiphilicly, is insoluble in organic solvent, thereby has limited its Application Areas.
Summary of the invention
The objective of the invention is to overcome above-mentioned N-alkylation or N, the deliquescent deficiency of N-alkylated chitosan provides a kind of amphiphilic chitosan-N that dissolves in organic solvent, the preparation method of N-double long-chain alkyl chitosan.
Technical scheme of the present invention is such: dissolve in the amphiphilic N of organic solvent, the preparation method of N-double long-chain alkyl chitosan, realized by following scheme:
It is in 3%～10% the aqueous acetic acid that chitosan is dissolved in percentage concentration, stirs, and making the mass percent concentration of chitosan in aqueous acetic acid is 2%～5%; Under 90 ℃～100 ℃ of the temperature of testing control, add aldehyde and phase-transfer catalyst, wherein, the consumption of aldehyde is 3-5 a times of theoretical amount, the weight ratio of phase-transfer catalyst and chitosan is 1: 3～1: 1; Behind the stirring reaction 6～10 hours, regulate pH to 6～8, slowly add 5% excessive～15%NaBH with NaOH solution
4Or NaCNBH
3The aqueous solution continued heated and stirred 2～3 hours; Regulate pH to slightly acidic with Glacial acetic acid then, add the aldehyde that the 2-3 of theoretical amount doubly measures again, stirring reaction was regulated pH to 6～8 with NaOH solution after 6～10 hours, slowly added 5% excessive～15%NaBH
4Or NaCNBH
3The aqueous solution continued heated and stirred 2～3 hours; After secondary reduction finishes, use hot acetone and hot water washed product successively, used the apparatus,Soxhlet's purifying again 24～48 hours; After product dries to constant weight, add the chloroform dissolving in vacuum drying oven, remove by filter insolubles, the solvent in the evaporate to dryness filtrate promptly gets the amphiphilic N that dissolves in organic solvent, N-double long-chain alkyl chitosan.
Above-mentioned aldehyde is octanal or capraldehyde or lauric aldehyde.
Above-mentioned phase-transfer catalyst is a sodium laurylsulfonate.
Above-mentionedly regulate pH with Glacial acetic acid and be specially pH=4～6 to weak acid.
Above-mentioned NaBH
4Or NaCNBH
3Consumption be 3～5 times of theoretical amount.
After adopting such scheme, under the phase-transfer catalyst effect, promote aldehyde and chitosan to form western Buddhist alkali, reduce western Buddhist alkali then, repeat this process again and synthesized N, N-double long-chain alkyl chitosan.Simple with the inventive method process operation, process is easy to control, and the N for preparing with the present invention, and N-double long-chain alkyl chitosan has following characteristics and advantage:
1, synthetic N, N-double long-chain alkyl chitosan dissolves in organic solvents such as chloroform, pyridine and tetrahydrofuran (THF).
2, synthetic N, N-double long-chain alkyl chitosan has amphiphilic.Simultaneously, that this type of chitosan-based material also has is nontoxic, biocompatibility and biodegradability, has therefore guaranteed the security of its production and use, can be applied to various fields such as medicine, agricultural chemicals, daily use chemicals, food, environmental protection, weaving and agricultural.
Description of drawings
Fig. 1 is N of the present invention, the synthetic route of N-double long-chain alkyl chitosan
Embodiment
In order to understand better and to implement, describe the amphiphilic N that the present invention dissolves in organic solvent in detail below in conjunction with embodiment, the preparation method of N-double long-chain alkyl chitosan.
Dissolve in the amphiphilic N of organic solvent, the preparation method of N-double long-chain alkyl chitosan, as shown in Figure 1, realized by the following step:
1, takes by weighing the 6.0g chitosan in the acetum of 180mL 5%, stirring and dissolving.
2, under 50 ℃, add 4 times the octanal and the 5g phase-transfer catalyst sodium laurylsulfonate of theoretical amount.100 ℃ of stirring reactions were regulated about pH to 7 with NaOH solution after 8 hours, slowly added 3 times 10%NaBH of theoretical amount
4The aqueous solution continued heated and stirred 2～3 hours.
3, regulate pH to slightly acidic with Glacial acetic acid, add octanal for the second time, the consumption of this octanal is 2 times of theoretical amount.100 ℃ of stirring reactions were regulated about pH to 7 with NaOH solution after 8 hours, slowly added 3 times 10%NaBH of theoretical amount
4The aqueous solution continued heated and stirred 2～3 hours.After secondary reduction finishes, regulate pH to 9～10 with NaOH solution, the product that is precipitated out is washed till neutrality with distilled water, removes excessive aldehyde and reduzate alcohol with acetone, uses the apparatus,Soxhlet's purifying again 48 hours.
4, after product dries to constant weight, add the chloroform dissolving in vacuum drying oven, remove by filter insolubles, the solvent in the evaporate to dryness filtrate dissolves in the amphiphilic N of organic solvent, N-double long-chain alkyl chitosan.
In the present invention, octanal can substitute with the capraldehyde or the lauric aldehyde of same molecular quality.
Claims (5)
1, dissolve in the amphiphilic N of organic solvent, the preparation method of N-double long-chain alkyl chitosan is characterized in that: realized by following scheme:
It is in 3%～10% the aqueous acetic acid that chitosan is dissolved in percentage concentration, stirs, and making the mass percent concentration of chitosan in aqueous acetic acid is 2%～5%; Under 90 ℃～100 ℃ of the temperature of testing control, add aldehyde and phase-transfer catalyst, wherein, the consumption of aldehyde is 3-5 a times of theoretical amount, the weight ratio of phase-transfer catalyst and chitosan is 1: 3～1: 1; Behind the stirring reaction 6～10 hours, regulate pH to 6～8, slowly add 5% excessive～15%NaBH with NaOH solution
4Or NaCNBH
3The aqueous solution continued heated and stirred 2～3 hours; Regulate pH to slightly acidic with Glacial acetic acid then, add the aldehyde that the 2-3 of theoretical amount doubly measures again, stirring reaction was regulated pH to 6～8 with NaOH solution after 6～10 hours, slowly added 5% excessive～15%NaBH
4Or NaCNBH
3The aqueous solution continued heated and stirred 2～3 hours; After secondary reduction finishes, use hot acetone and hot water washed product successively, used the apparatus,Soxhlet's purifying again 24～48 hours; After product dries to constant weight, add the chloroform dissolving in vacuum drying oven, remove by filter insolubles, the solvent in the evaporate to dryness filtrate promptly gets the amphiphilic N that dissolves in organic solvent, N-double long-chain alkyl chitosan.
2, the amphiphilic N that dissolves in organic solvent according to claim 1, the preparation method of N-double long-chain alkyl chitosan is characterized in that: above-mentioned aldehyde is octanal or capraldehyde or lauric aldehyde.
3, the amphiphilic N that dissolves in organic solvent according to claim 1, the preparation method of N-double long-chain alkyl chitosan is characterized in that: above-mentioned phase-transfer catalyst is a sodium laurylsulfonate.
4, the amphiphilic N that dissolves in organic solvent according to claim 1, the preparation method of N-double long-chain alkyl chitosan is characterized in that: above-mentionedly regulate pH with Glacial acetic acid and be specially pH=4～6 to weak acid.
5, the amphiphilic N that dissolves in organic solvent according to claim 1, the preparation method of N-double long-chain alkyl chitosan is characterized in that: above-mentioned NaBH
4Or NaCNBH
3Consumption be 3～5 times of theoretical amount.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100226348A CN100526334C (en) | 2005-12-21 | 2005-12-21 | Method for preparing organic solvent soluble amphiphilic N,N-dilong chain alkyl chitosan |
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|---|---|---|---|
| CNB2005100226348A CN100526334C (en) | 2005-12-21 | 2005-12-21 | Method for preparing organic solvent soluble amphiphilic N,N-dilong chain alkyl chitosan |
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| CN1803852A true CN1803852A (en) | 2006-07-19 |
| CN100526334C CN100526334C (en) | 2009-08-12 |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107151264A (en) * | 2011-03-23 | 2017-09-12 | 浙江医药股份有限公司新昌制药厂 | Antimicrobial-oritavancin derivative and pharmaceutical composition, with and its production and use |
| CN107163164A (en) * | 2017-06-02 | 2017-09-15 | 广西师范学院 | The preparation method of cross-linking type macromolecular light stabilizer |
| CN109970884A (en) * | 2019-04-22 | 2019-07-05 | 华侨大学 | It is a kind of to prepare high substitution N, the method for N- double long-chain alkyl chitosan using catalytic hydrogen reduction |
| CN114163740A (en) * | 2021-12-06 | 2022-03-11 | 浙江大学 | Method for improving hydrophilicity of polyolefin elastomer |
| CN115010336A (en) * | 2022-06-27 | 2022-09-06 | 上海交通大学 | Method for producing methane through anaerobic digestion of sludge based on slow-release choline |
-
2005
- 2005-12-21 CN CNB2005100226348A patent/CN100526334C/en active Active
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107151264A (en) * | 2011-03-23 | 2017-09-12 | 浙江医药股份有限公司新昌制药厂 | Antimicrobial-oritavancin derivative and pharmaceutical composition, with and its production and use |
| CN107151264B (en) * | 2011-03-23 | 2021-11-23 | 浙江医药股份有限公司新昌制药厂 | Novel glycopeptide antibiotic derivative, pharmaceutical composition, preparation method and application thereof |
| CN107163164A (en) * | 2017-06-02 | 2017-09-15 | 广西师范学院 | The preparation method of cross-linking type macromolecular light stabilizer |
| CN107163164B (en) * | 2017-06-02 | 2019-06-04 | 广西师范学院 | The preparation method of cross-linking type macromolecular light stabilizer |
| CN109970884A (en) * | 2019-04-22 | 2019-07-05 | 华侨大学 | It is a kind of to prepare high substitution N, the method for N- double long-chain alkyl chitosan using catalytic hydrogen reduction |
| CN114163740A (en) * | 2021-12-06 | 2022-03-11 | 浙江大学 | Method for improving hydrophilicity of polyolefin elastomer |
| CN115010336A (en) * | 2022-06-27 | 2022-09-06 | 上海交通大学 | Method for producing methane through anaerobic digestion of sludge based on slow-release choline |
| CN115010336B (en) * | 2022-06-27 | 2023-10-20 | 上海交通大学 | Method for producing methane by sludge anaerobic digestion based on slow-release choline |
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|---|---|
| CN100526334C (en) | 2009-08-12 |
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