CN103422339A - Method for preparing antibacterial functional cellulosic fibers - Google Patents
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Abstract
The invention discloses a method for preparing antibacterial functional cellulosic fibers. The method comprises the steps of using a cross-linking agent for enabling cyclodextrin to be arranged on the cellulosic fibers in a stem grafting mode through a chemical reaction, then utilizing the cyclodextrin on the fibers to conduct clathration on antibacterial agents, and in the preparing process, conducting ultrasound pretreatment on a reaction system comprising the cyclodextrin, the cross-linking agent, a catalyst and the cellulosic fibers. According to the method, the defect that in the prior art, the solid loading efficiency of the cyclodextrin is low, the preparation time is short, the efficiency is high, the antibacterial and anti-infection functional cellulosic fibers with the slow-release performance and paper products of the cellulosic fibers can be manufactured, and the functional cellulosic fibers have good market prospects.
Description
Technical field
The present invention relates to the preparation method of anti-bacterial fibre, particularly a kind of preparation method of functional antibacterial fibre cellulose fiber.
Background technology
In life, people inevitably touch the microorganisms such as various bacteriums, fungi, and these microorganisms, under suitable external condition, spread disease by modes such as contacts, thereby affect people's healthy and normal work, studying and living.Therefore, along with scientific and technical development and the raising of people's living standard, research, the development and production of anti-bacterial fibre more and more come into one's own.
Anti-bacterial fibre adopts the material that the method for physics or chemistry can bacteria growing inhibiting to introduce fiber surface and inner making.Physical method mainly contains co-blended spinning method, composite spinning method and finishing method.Chemical method is mainly the method by MOLECULE DESIGN, utilizes the means such as copolymerization, grafting, macromolecular reaction to change the chemical constitution of fiber, generates antibiotic group, thereby gives fiber with antibacterial activity.Compare with Physical, there is on good anti-bacterial effect, lasting, good hand touch, fiber the advantages such as non-cohesive resin with the standby anti-bacterial fibre of fibre chemistry modification legal system.But to the material on fiber, be mainly halogen compound class, quaternary ammonium salt, isothiazole class and guanidinesalt class etc. by chemical method graft copolymerization, the positions such as these materials and skin directly contact and can cause problems to occur: on the one hand, due to the skin of the different people sensitivity difference to chemicals, the antiseptic that is attached to fiber surface allows those skins produce sense of discomfort to chemicals than more sensitive crowd possibly, allergic symptom even occurs; On the other hand, these medicines have certain excitant, and these after thering is irritating material and skin directly contacting, likely can cause pruitus, rubescent, play the malaise symptoms such as goose pimples.Therefore, when preparing anti-bacterial fibre, should avoid these antibacterials directly to contact with positions such as skins.
The cyclic oligomer sugar compounds that cyclodextrin (being called for short CD) is connected with α-Isosorbide-5-Nitrae type glycosidic bond by 6 above glucopyranose units, can be divided into α-CD, β-CD, γ-CD etc. according to glucose unit number (6,7,8).It has hydrophilic, the inboard hydrophobic cavity structure in the outside, can carry out inclusion with multiple small-molecule substance, has shielding, controls the functions such as release, active protection, and it has the characteristics such as nontoxic, non-stimulated, biodegradable in addition.Therefore, cyclodextrin and good envelope and the fiber of derivative thereof are organically combined, can form different functional fibers, to meet people's various demands.CN 1940171A discloses a kind of preparation method of functional antibacterial fibre, the epoxychloropropane of take is received cyclodextrin on cellulose fibre as crosslinking agent, form the polymer of cyclodextrin and cellulose fibre, this polymer inclusion chloramphenicol, obtain functional antibacterial fibre.Wan Jun-hua etc. (Carbohydrate Polymers, 2008,72:695-710) take a chloro-s-triazine as crosslinking agent, that cyclodextrin is immobilized to cellulose, then utilize the hydrophobic cavity inclusion antiseptic miconazole nitrate of cyclodextrin to make anti-bacterial fibre.Although these methods can make the fiber that antibacterial effect is good, but exist the limitation of following aspect: epoxychloropropane method technique is simple, but the utilization rate of itself is low, under alkali condition, hydrolysis also can occur in epoxychloropropane in addition, have a large amount of carcinogenic products and produce, must be separated and remove by certain technology; In one chloro-s-triazine method, easily moisture absorption of a chloro-s-triazine itself, thereby make its activity decreased, and on the high side.
The polycarboxylic acids method is to study at present more a kind of Novel ring dextrin solid support method, and it is also fewer by the polycarboxylic acids method, cyclodextrin to be grafted on cellulose fibre to the report for preparing anti-bacterial fibre.(food and fermentation industries, 2008,34 (2): 16-20) take polyacrylic acid as crosslinking agent such as Qian Liangliang, beta-schardinger dextrin-is immobilized to cellulose, then utilize this cellulose to carry out embedding to volatilization food antiseptic cinnamic acid, obtain antibacterial cellulose, but immobilized efficiency is on the low side.Therefore, how by cyclodextrin and derivative thereof and cellulose fibre is efficient, lasting and the combination of environmental protection, become the hot issue of anti-bacterial fibre research and application.
Summary of the invention
In order to overcome the above-mentioned shortcoming and defect of prior art, the object of the present invention is to provide the preparation method of the functional antibacterial fibre cellulose fiber that a kind of immobilized efficiency is high, preparation time is short, and efficiency is high.
Purpose of the present invention is achieved through the following technical solutions:
A kind of preparation method of functional antibacterial fibre cellulose fiber comprises the following steps:
(1) cellulose fibre is joined in the sodium hydroxide solution of 1.5～3mol/L, the weight ratio of cellulose fibre and sodium hydroxide solution is 1:10～1:40, at 40～70 ℃ of lower swelling 1～4h, be washed with distilled water to neutrality, obtain the cellulose fibre that swelling is good;
(2) add the cyclodextrin of 50～150g, the crosslinking agent of 50～100g, the catalyst of 5～25g in every liter of deionized water, under 50～70 ℃, heat 15～30min, after dissolving fully, obtain reaction solution; Add the cellulose fibre that swelling is good in reaction solution, after swelling 15～30min, then put into ultrasonic 15～60min in ultrasonic cleaner, supersonic frequency is 20～80KHz; Finally put in 140～180 ℃ of air dry ovens after curing reaction 15～60min, with after 50～70 ℃ of hot washes the cellulose fibre of grafted cyclodextrin; Wherein, the cellulose fibre that swelling is good and the mass ratio of reaction solution are 1:20～1:40;
(3) cellulose fibre of grafted cyclodextrin step (2) obtained adds in the antibacterials solution that concentration is 2～6g/L, under room temperature with the hunting speed of 100～200rpm, the 2～8h that vibrates in shaking table, with after deionized water or organic solvent washing, after the vacuum drying chamber drying, obtain having the functional antibacterial fibre cellulose fiber; Wherein, the weight ratio of the cellulose fibre of described grafted cyclodextrin and antibacterials solution is 1:20～1:50.
Described cyclodextrin is beta-schardinger dextrin-.
Described crosslinking agent is citric acid or butanetetra-carboxylic acid.
Described catalyst is a kind of in inferior sodium phosphate, sodium dihydrogen phosphate or sodium hydrogen phosphate.
Described antibacterials are a kind of in Ciprofloxacin Hydrochloride, trichlorine hydroxyl methyl ether or butyl p-hydroxybenzoate.
Described organic solvent is a kind of in methyl alcohol, ethanol or acetone.
Compared with prior art, the present invention has the following advantages and beneficial effect:
(1) the present invention carries out ultrasonic preliminary treatment by the reaction system to comprising cyclodextrin, crosslinking agent, catalyst, cellulose fibre, destroy the crystalline texture in cellulose by hyperacoustic resonance, make structure relatively loose, thereby solution more easily enters into cellulosic molecule, improve the reactivity of cellulose fibre, thereby improved the immobilized efficiency of cyclodextrin.
(2) the present invention is by being grafted to cyclodextrin on cellulose fibre, form cyclodextrin modified fiber, recycling is received the cyclodextrin encapsulated antibacterials on fiber, realize the shielding action of the cellulose fibre of cyclodextrin grafting to medicine, control the release of medicine, further its drug effect of performance, reduce side effect, the high availability to medicine.
(3) the functional antibacterial fibre cellulose fiber that prepared by the present invention, after arranging, can also carry out inclusion simply again after medicine discharges fully, finally realizes permanent lasting activity, has greatly strengthened expectation function or the function of commodity.
(4) the functional antibacterial fibre cellulose fiber that prepared by the present invention, on cellulose fibre, the percent grafting of cyclodextrin is 3～15%; The load capacity of antibacterials is 10～30mg/g bone dry fiber; Antibacterial effect is 10～100%.
(5) preparation method of the present invention is simple to operate, with low cost.
The accompanying drawing explanation
Infrared spectrogram before and after the fibre grafting cyclodextrin that Fig. 1 is embodiments of the invention 1.
Cumulative release figure in time under the fiber room temperature of carrying Ciprofloxacin Hydrochloride that Fig. 2 is embodiments of the invention 1 preparation.
The specific embodiment
Below in conjunction with embodiment, the present invention is described in further detail, but embodiments of the present invention are not limited to this.
Embodiment 1
Cellulose fibre is put into to swelling 1h in the sodium hydroxide solution of 1.5mol/L, the weight ratio of cellulose fibre and sodium hydroxide solution is 1:20; Be washed with distilled water to neutrality, standby; Take 5g beta-schardinger dextrin-, 5g citric acid, 0.5g inferior sodium phosphate and join respectively in the 50ml deionized water, stir 15min and make it to dissolve fully under 50 ℃, obtain reaction solution.By the 2g swelling, good cellulose fibre is dipped in reaction solution, after swollen 15min, and then put into ultrasonic 55min in ultrasonic cleaner, frequency is 80KHz, then put into curing reaction 15min in 150 ℃ of air dry ovens, use afterwards 50 ℃ of hot wash fibers 3 times, obtain the fiber of graft beta-cyclodextrin.The above-mentioned fiber of 1g is joined in the Ciloxan that 50ml concentration is 2g/l, absorption 4h vibrates under room temperature in the constant-temperature table of 200rpm, after filtration, with deionized water, wash 3 times, then dry 24h in 60 ℃ of vacuum drying chambers, obtain the fiber (sample 1) of load Ciprofloxacin Hydrochloride.
As can be seen from Figure 1: with graft fibres not, compare, the fiber of grafted cyclodextrin is at 1708cm
-1Near new absorption vibration peak is arranged, this is the characteristic peak of ester group.As can be seen from Figure 2: the release of Ciprofloxacin Hydrochloride from the grafted cyclodextrin fiber has the characteristics of burst release and the slow release in later stage at initial stage, after initial 30min release has reached 36%, 240min, discharges and substantially reaches balance.
The antibacterial effect of functional antibacterial fibre cellulose fiber prepared by the present embodiment is in Table 1.
For being contrasted, the present embodiment has also prepared comparative sample 1, and preparation process is except without ultrasonic processing, all the other and sample 1 with, comparing result is in Table 1.
Embodiment 2
Cellulose fibre is put into to swelling 2h in the sodium hydroxide solution of 2mol/L, the weight ratio of cellulose fibre and sodium hydroxide solution is 1:30; Be washed with distilled water to neutrality, standby; Take 5g beta-schardinger dextrin-, 6g citric acid, 0.75g sodium dihydrogen phosphate and join in the 50ml deionized water, stir 20min and make it to dissolve fully under 60 ℃, obtain reaction solution.By the 3g swelling, good cellulose fibre is dipped in reaction solution, after swollen 20min, and then put into ultrasonic 30min in ultrasonic cleaner, frequency is 20KHz, then put into curing reaction 20min in 160 ℃ of air dry ovens, use afterwards 60 ℃ of hot wash fibers 3 times, obtain the fiber of graft beta-cyclodextrin; The above-mentioned fiber of 2g is put in the Ciloxan that 50ml concentration is 4g/l, absorption 6h vibrates under room temperature in the constant-temperature table of 200rpm, after filtration, with deionized water, wash 3 times, then dry 24h in 60 ℃ of vacuum drying chambers, obtain the fiber (sample 2) of load Ciprofloxacin Hydrochloride.
The antibacterial effect of functional antibacterial fibre cellulose fiber prepared by the present embodiment is in Table 1.
For being contrasted, the present embodiment has also prepared comparative sample 2, and preparation process is except without ultrasonic processing, all the other and sample 2 with, comparing result is in Table 1.
Embodiment 3
Cellulose fibre is put into to swelling 3h in the sodium hydroxide solution of 3mol/L, the weight ratio of cellulose fibre and sodium hydroxide solution is 1:40; Be washed with distilled water to neutrality, standby; Take 5g beta-schardinger dextrin-, 5g citric acid, 1g sodium hydrogen phosphate and join in the 50ml deionized water, stir 30min and make it to dissolve fully under 70 ℃, obtain reaction solution.By the 4g swelling, good cellulose fibre is dipped in reaction solution, after swollen 30min, and then put into ultrasonic 50min in ultrasonic cleaner, frequency is 45KHz, then put into curing reaction 30min in 170 ℃ of air dry ovens, use afterwards 70 ℃ of hot wash fibers 3 times, obtain the fiber of graft beta-cyclodextrin; The above-mentioned fiber of 1g is put in the trichlorine hydroxyl methyl ether solution that 50ml concentration is 6g/l, absorption 8h vibrates under room temperature in the constant-temperature table of 200rpm, after filtration, with ethanol washing 3 times, dry 24h in 60 ℃ of vacuum drying chambers then, obtain the fiber (sample 3) of load trichlorine hydroxyl methyl ether.
The antibacterial effect of functional antibacterial fibre cellulose fiber prepared by the present embodiment is in Table 1.
For being contrasted, the present embodiment has also prepared comparative sample 3, and preparation process is except without ultrasonic processing, all the other and sample 3 with, comparing result is in Table 1.
Embodiment 4
Cellulose fibre is put into to swelling 2h in the sodium hydroxide solution of 2mol/L, the weight ratio of cellulose fibre and sodium hydroxide solution is 1:30; Be washed with distilled water to neutrality, standby; Take 5g beta-schardinger dextrin-, 7g citric acid, 0.75g sodium dihydrogen phosphate and join in the 50ml deionized water, stir 20min and make it to dissolve fully under 60 ℃, obtain reaction solution.By the 3g swelling, good cellulose fibre is dipped in reaction solution, after swollen 20min, and then put into ultrasonic 25min in ultrasonic cleaner, frequency is 70KHz, then put into curing reaction 20min in 160 ℃ of air dry ovens, use afterwards 60 ℃ of hot wash fibers 3 times, obtain the fiber of graft beta-cyclodextrin; The above-mentioned fiber of 2g is put in the butyl p-hydroxybenzoate solution that 50ml concentration is 4g/l, absorption 6h vibrates under room temperature in the constant-temperature table of 200rpm, after filtration, with ethanol, wash 3 times, then dry 24h in 60 ℃ of vacuum drying chambers, obtain the fiber (sample 4) of load butyl p-hydroxybenzoate.
The antibacterial effect of functional antibacterial fibre cellulose fiber prepared by the present embodiment is in Table 1.
For being contrasted, the present embodiment has also prepared comparative sample 4, and preparation process is except without ultrasonic processing, all the other and sample 4 with, comparing result is in Table 1.
Embodiment 5
Cellulose fibre is put into to swelling 1h in the sodium hydroxide solution of 1.5mol/L, the weight ratio of cellulose fibre and sodium hydroxide solution is 1:20; Be washed with distilled water to neutrality, standby; Take 5g beta-schardinger dextrin-, 5g butanetetra-carboxylic acid, 0.5g inferior sodium phosphate and join in the 50ml deionized water, stir 15min and make it to dissolve fully under 50 ℃, obtain reaction solution.By the 2g swelling, good cellulose fibre is dipped in reaction solution, after swollen 15min, and then put into ultrasonic 45min in ultrasonic cleaner, frequency is 30KHz, then put into curing reaction 15min in 150 ℃ of air dry ovens, use afterwards 50 ℃ of hot wash fibers 3 times, obtain the fiber of graft beta-cyclodextrin; The above-mentioned fiber of 1g is put in the Ciloxan that 50mL concentration is 2g/l, absorption 4h vibrates under room temperature in the constant-temperature table of 200rpm, after filtration, with deionized water, wash 3 times, then dry 24h in 60 ℃ of vacuum drying chambers, obtain the fiber (sample 5) of load Ciprofloxacin Hydrochloride.
The antibacterial effect of functional antibacterial fibre cellulose fiber prepared by the present embodiment is in Table 1.
For being contrasted, the present embodiment has also prepared comparative sample 5, and preparation process is except without ultrasonic processing, all the other and sample 5 with, comparing result is in Table 1.
Embodiment 6
Cellulose fibre is put into to swelling 2h in the sodium hydroxide solution of 2mol/L, the weight ratio of cellulose fibre and sodium hydroxide solution is 1:30; Be washed with distilled water to neutrality, standby; Take 5g beta-schardinger dextrin-, 7g butanetetra-carboxylic acid, 0.75g sodium hydrogen phosphate and join in the 50ml deionized water, stir 20min and make it to dissolve fully under 60 ℃, obtain reaction solution.By the 3g swelling, good fiber is dipped in reaction solution, after swollen 20min, and then put into ultrasonic 30min in ultrasonic cleaner, frequency is 60KHz, then put into curing reaction 20min in 160 ℃ of air dry ovens, use afterwards 60 ℃ of hot wash fibers 3 times, obtain the fiber of graft beta-cyclodextrin; The above-mentioned fiber of 1g is put in the Ciloxan that 50mL concentration is 4g/l, absorption 6h vibrates under room temperature in the constant-temperature table of 200rpm, after filtration, with acetone washing 3 times, dry 24h in 60 ℃ of vacuum drying chambers then, obtain the fiber (sample 6) of load Ciprofloxacin Hydrochloride.
The antibacterial effect of functional antibacterial fibre cellulose fiber prepared by the present embodiment is in Table 1.
For being contrasted, the present embodiment has also prepared comparative sample 6, and preparation process is except without ultrasonic processing, all the other and sample 6 with, comparing result is in Table 1.
Embodiment 7
Cellulose fibre is put in the sodium hydroxide solution of 3mol/L, wherein the weight ratio of cellulose fibre and sodium hydroxide solution is 1:40, at 70 ℃ of lower swelling 4h, is washed with distilled water to neutrality, standby; Take 7.5g beta-schardinger dextrin-, 5g butanetetra-carboxylic acid, 1.25g inferior sodium phosphate and join in the 50ml deionized water, stir 30min and make it to dissolve fully under 70 ℃, obtain reaction solution.By the 1.6g swelling, good cellulose fibre is dipped in reaction solution, after swollen 30min, and then put into ultrasonic 60min in ultrasonic cleaner, frequency is 80KHz, then put into curing reaction 30min in 180 ℃ of air dry ovens, use afterwards 70 ℃ of hot wash fibers 3 times, obtain the fiber of graft beta-cyclodextrin; The fiber of graft beta-cyclodextrin is put in the trichlorine hydroxyl methyl ether solution that concentration is 6g/l, and the weight ratio of the cellulose fibre of grafted cyclodextrin and trichlorine hydroxyl methyl ether solution is 1:50; Under room temperature in the constant-temperature table of 200rpm vibration absorption 8h, after filtering, by methanol wash 3 times, dry 24h in 60 ℃ of vacuum drying chambers then, obtain the fiber (sample 7) of load trichlorine hydroxyl methyl ether.
The antibacterial effect of functional antibacterial fibre cellulose fiber prepared by the present embodiment is in Table 1.
For being contrasted, the present embodiment has also prepared comparative sample 7, and preparation process is except without ultrasonic processing, all the other and sample 7 with, comparing result is in Table 1.
Embodiment 8
Cellulose fibre is put in the sodium hydroxide solution of 1.5mol/L, wherein the weight ratio of cellulose fibre and sodium hydroxide solution is 1:10, at 40 ℃ of lower swelling 1h, is washed with distilled water to neutrality, standby; Take 0.25g beta-schardinger dextrin-, 0.25g butanetetra-carboxylic acid, 0.25g sodium hydrogen phosphate and join and add in the 50ml deionized water, stir 15min and make it to dissolve fully under 50 ℃, obtain reaction dissolvent.By the 2.5g swelling, good cellulose fibre is dipped in reaction dissolvent, after swelling 15min, then put into curing reaction 15min in the air dry oven of 140 ℃, then put into ultrasonic 15min in ultrasonic cleaner, frequency is 20KHz, use afterwards 50 ℃ of hot wash fibers 3 times, obtain the fiber of graft beta-cyclodextrin.The fiber of graft beta-cyclodextrin is put in the butyl p-hydroxybenzoate solution of 2g/l, the weight ratio of the cellulose fibre of grafted cyclodextrin and butyl p-hydroxybenzoate solution is 1:20; Under room temperature in the constant-temperature table of 100rpm vibration absorption 2h, after filtration, with ethanol washing 3 times, dry 24h in 60 ℃ of vacuum drying chambers then, obtain the fiber (sample 8) of load butyl p-hydroxybenzoate.
The antibacterial effect of functional antibacterial fibre cellulose fiber prepared by the present embodiment is in Table 1.
For being contrasted, the present embodiment has also prepared comparative sample 8, and preparation process is except without ultrasonic processing, all the other and sample 8 with, comparing result is in Table 1.
The antibacterial effect of the sample of table 1 embodiment 1～8 preparation
Above-described embodiment is preferably embodiment of the present invention; but embodiments of the present invention are not limited by the examples; other any do not deviate from change, the modification done under Spirit Essence of the present invention and principle, substitutes, combination, simplify; all should be equivalent substitute mode, within being included in protection scope of the present invention.
Claims (6)
1. the preparation method of a functional antibacterial fibre cellulose fiber, is characterized in that, comprises the following steps:
(1) cellulose fibre is joined in the sodium hydroxide solution of 1.5～3mol/L, the weight ratio of cellulose fibre and sodium hydroxide solution is 1:10～1:40, at 40～70 ℃ of lower swelling 1～4h, be washed with distilled water to neutrality, obtain the cellulose fibre that swelling is good;
(2) add the cyclodextrin of 50～150g, the crosslinking agent of 50～100g, the catalyst of 5～25g in every liter of deionized water, under 50～70 ℃, heat 15～30min, after dissolving fully, obtain reaction solution; Add the cellulose fibre that swelling is good in reaction solution, after swelling 15～30min, then put into ultrasonic 15～60min in ultrasonic cleaner, supersonic frequency is 20～80KHz; Finally put in 140～180 ℃ of air dry ovens after curing reaction 15～60min, with after 50～70 ℃ of hot washes the cellulose fibre of grafted cyclodextrin; Wherein, the cellulose fibre that swelling is good and the mass ratio of reaction solution are 1:20～1:40;
(3) cellulose fibre of grafted cyclodextrin step (2) obtained adds in the antibacterials solution that concentration is 2～6g/L, under room temperature with the hunting speed of 100～200rpm, the 2～8h that vibrates in shaking table, with after deionized water or organic solvent washing, after the vacuum drying chamber drying, obtain having the functional antibacterial fibre cellulose fiber; Wherein, the weight ratio of the cellulose fibre of described grafted cyclodextrin and antibacterials solution is 1:20～1:50.
2. the preparation method of functional antibacterial fibre cellulose fiber according to claim 1, is characterized in that, described cyclodextrin is beta-schardinger dextrin-.
3. the preparation method of functional antibacterial fibre cellulose fiber according to claim 1, is characterized in that, described crosslinking agent is citric acid or butanetetra-carboxylic acid.
4. the preparation method of functional antibacterial fibre cellulose fiber according to claim 1, is characterized in that, described catalyst is a kind of in inferior sodium phosphate, sodium dihydrogen phosphate or sodium hydrogen phosphate.
5. the preparation method of functional antibacterial fibre cellulose fiber according to claim 1, is characterized in that, described antibacterials are a kind of in Ciprofloxacin Hydrochloride, trichlorine hydroxyl methyl ether or butyl p-hydroxybenzoate.
6. the preparation method of functional antibacterial fibre cellulose fiber according to claim 1, is characterized in that, described organic solvent is a kind of in methyl alcohol, ethanol or acetone.
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| CN103981690A (en) * | 2014-04-23 | 2014-08-13 | 桐乡市濮院毛针织技术服务中心 | Stinking-proof finishing method of wool fabric |
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| CN103844274A (en) * | 2014-03-26 | 2014-06-11 | 光明乳业股份有限公司 | Low-cholesterol dairy product, grafted beta-cyclodextrin rice bran fibers and preparation method and application thereof |
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