CN110306340A - Antimicrobial natural textile material of surface modification borneol and the preparation method and application thereof - Google Patents
Antimicrobial natural textile material of surface modification borneol and the preparation method and application thereof Download PDFInfo
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- CN110306340A CN110306340A CN201910411303.5A CN201910411303A CN110306340A CN 110306340 A CN110306340 A CN 110306340A CN 201910411303 A CN201910411303 A CN 201910411303A CN 110306340 A CN110306340 A CN 110306340A
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- Prior art keywords
- borneol
- textile material
- natural
- benzoic acid
- surface modification
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- 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
- D06M13/10—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 oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
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- 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
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
- D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
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- 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
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
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- 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
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
-
- 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
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
Abstract
A kind of antimicrobial natural textile material the present invention relates to surface modification borneol is the new antibacterial strategy using surface three-dimensional chemistry, the natural weave material and 4- aldehyde benzoic acid borneol derivative being coupled by amino silicone are made, reaction condition in its preparation process is mild, and preparation process is simple.The antimicrobial natural textile material is a kind of non-release type antibacterial textile material, will not bactericide-release kill microorganism, but sticking for microorganism is influenced by material surface stereochemical structure, and can guarantee safety in utilization, it will not cause skin irritatin sensitization, skin will not be destroyed and have flora by oneself；Meanwhile the material has anti-adhesion well to bacterium and fungi, effectively can muchly inhibit sticking for bacterium and fungi, stable structure is water-fastness.The antimicrobial natural textile material is a kind of safe and stable, environmentally friendly novel antibacterial natural fabric, can be widely applied to the industries such as medical treatment, health, environmental protection and clothes.
Description
Technical field
The invention belongs to biological antibiotic Material Field, be related to a kind of surface modification borneol antimicrobial natural textile material and its
Preparation method and application.
Background technique
Natural fabric is widely used in the schedule life of people, such as clothes, sheet, mask, white clothes and medical yarn
Cloth etc., but also provide breeding ground and medium simultaneously for harmful microbe growth and breeding and propagation, in use serious prestige
Coerce the health of the mankind.With advances in technology with the raising of the safe and healthy consciousness of people, anti-microbial property of the people to textile
Higher requirements are also raised.Therefore, how to meet and assign its height under the premise of not influencing textile appearance and safe handling
Imitating lasting antibacterial functions becomes the research hotspot of nowadays academia and industrial circle paid close attention to jointly.
There are mainly two types of existing antibacterial fabric preparation methods: one is antibacterial agent is added in textile raw material to be made
Then anti-bacterial fibre is woven into various antibiotic fabric products again.This method antibacterial effect is more longlasting, and washability is good, but processes
Technology difficulty is big, requires antibacterial agent high；Another kind is that antibacterial agent is added during fabrics printing and dyeing final finishing, is made various
Antibacterial fabric.This method is simpler with respect to processing technology, but there is also durable antibacterial effect is poor, washability is poor to be asked
Topic.Existing antibacterial agent mainly includes antibiotics, metal and its esters, doped quaternary ammonium salt class and halogen amine etc..But also all exist anti-
Bacterium effect is not lasting, the poor problem of washability, while there is also antibacterial agent releases to cause toxicity, skin irritation and drug resistance
The risk of property.Therefore Development of Novel is more stable, is efficiently of great significance with the antibacterial fabric preparation method of safety.
Summary of the invention
The technical problem to be solved by the present invention is to aiming at the problems existing in the prior art, provide a kind of surface modification dragon
The antimicrobial natural textile material of brain, the material effectively can muchly inhibit sticking for bacterium and fungi, and stable structure is water-fastness, and
To no skin irritation, nontoxicity, drug resistance will not be caused.
The present invention also provides a kind of preparation method of above-mentioned antimicrobial natural textile material, this method utilizes surface three-dimensional
The new antibacterial strategy learned, reaction condition is mild, and preparation method is simple, can be widely applied to medical treatment, health, environmental protection and clothes etc. and produces
Industry.
For this purpose, first aspect present invention provides a kind of antimicrobial natural textile material of surface modification borneol, pass through ammonia
The natural weave material and 4- aldehyde benzoic acid borneol derivative of radical siloxane coupling are constituted.
According to the present invention, the configuration of the 4- aldehyde benzoic acid borneol derivative includes D- borneol, L-Borneol and IsoBorneol
One or more of.
In some embodiments of the invention, the molecular structural formula such as formula (I) of the 4- aldehyde benzoic acid borneol derivative
It is shown:
In the present invention, the amino silicone includes 3- aminopropyl triethoxy siloxanes, 3- aminopropyl trimethoxy
One or more of radical siloxane and 4- aminobutyl triethoxy siloxanes；Optionally, in the antibacterial of surface modification borneol
In natural weave material, the day that is coupled 4- aldehyde benzoic acid borneol Derivatives Modified to amino silicone by schiff base reaction
Right textile material surface.
According to the present invention, antimicrobial natural textile material is able to suppress or prevents microorganism adhering in its surface.
In some embodiments of the invention, the microorganism includes bacterium and/or fungi.
In some embodiments of the invention, the natural weave material includes cotton fibre material, cotton fiber textile material
One or more of material, flaxen fiber material, flaxen fiber textile material, bamboo fiber material and bamboo fibre fabric material.
Second aspect of the present invention provides a kind of preparation method of the antimicrobial natural textile material of surface modification borneol, packet
It includes:
Natural weave material is placed in amino silicone finishing fluid and carries out immersion treatment, then takes out by step B, heating,
Washing, dries, obtains the natural weave material that surface modification has aminosilane groups；
It is derivative to be placed in 4- aldehyde benzoic acid borneol by step C for the natural weave material that surface modification has aminosilane groups
Immersion treatment is carried out in object finishing fluid, is washed out, dries, and the antimicrobial natural textile material of surface modification borneol is made.
According to the method for the present invention, the amino silicone finishing fluid is dissolved in I organic solvent by amino silicone and is formed.
In some embodiments of the invention, the I organic solvent includes toluene and/or acetone.
In the present invention, the amino silicone includes 3-aminopropyltriethoxysilane, 3- aminopropyl trimethoxy
One or more of silane and 4- ammobutyltriethoxysilane.
In some embodiments of the invention, the content of amino silicone is 5- in the amino silicone finishing fluid
15vol%.
According to the method for the present invention, the 4- aldehyde benzoic acid borneol derivative finishing fluid is derivative by 4- aldehyde benzoic acid borneol
Object is dissolved in Section II organic solvent and is formed.
In some embodiments of the invention, the 1I organic solvent includes ethyl alcohol, one of methanol and acetone or
It is several.
In the present invention, the configuration of the 4- aldehyde benzoic acid borneol derivative includes D- borneol, L-Borneol and IsoIn borneol
One or more.
In some embodiments of the invention, 4- aldehyde benzoic acid in the 4- aldehyde benzoic acid borneol derivative finishing fluid
The content of borneol derivative is 0.01-0.05g/mL.
According to the method for the present invention, in stepb, the temperature of the immersion treatment is room temperature.
In some embodiments of the invention, in stepb, the time of the immersion treatment is 10-60min.
In some embodiments of the invention, in stepb, the temperature of the heating is 50-100 DEG C.
In some embodiments of the invention, in stepb, the time of the heating is 0.5-3h.
According to the method for the present invention, in step C, the temperature of the immersion treatment is room temperature.
In some embodiments of the invention, in step C, the time of the immersion treatment is 1-3h.
Third aspect present invention provides the antimicrobial natural weaving of surface modification borneol as described in the first aspect of the invention
The antimicrobial natural textile material of material or the surface modification borneol of method preparation as described in respect of the second aspect of the invention is anti-in preparation
Application in bacterium natural textile product.
In some embodiments of the invention, the natural weave material includes cotton fibre material, cotton fiber textile material
One or more of material, flaxen fiber material, flaxen fiber textile material, bamboo fiber material and bamboo fibre fabric material.
The antimicrobial natural textile material of surface modification borneol provided by the present invention is to first pass through amino silicone modification day
Right textile material makes its surface exposure active amino, then 4- aldehyde benzoic acid borneol derivative is passed through the seat with surface amino groups
The reaction of husband's alkali is modified.This can be understood as modifying 4- aldehyde benzoic acid borneol Derivatives Modified to amino silane natural
Textile material surface enables natural weave material effectively to inhibit sticking for bacterium and fungi, to realize natural weave material
The purpose of antimicrobial protection.
The antimicrobial natural textile material of surface modification borneol provided by the present invention is to utilize the new anti-of surface three-dimensional chemistry
The novel antimicrobial natural textile material of one kind made from bacterium strategy, the schiff base reaction mild condition in preparation method prepare work
Skill is simple.
The antimicrobial natural textile material of surface modification borneol provided by the present invention is a kind of non-release type antibacterial weaving material
Material, will not bactericide-release kill microorganism, but sticking for microorganism influenced by material surface stereochemical structure, and
It can guarantee safety in utilization, skin irritatin sensitization will not be caused, skin will not be destroyed and have flora by oneself；Meanwhile the material is to thin
Bacterium and fungi have anti-adhesion well, effectively can muchly inhibit sticking for bacterium and fungi, and stable structure is water-fastness,
Its antibacterium adherence rate is greater than 95%, and antimycotic persistence is longer than 30 days, and resistance to 50 times mechanical washings.Therefore, the present invention is mentioned
The antimicrobial natural textile material of the surface modification borneol of confession is a kind of safe and stable, environmentally friendly novel antibacterial natural fabric, can
It is widely used in the industries such as medical treatment, health, environmental protection and clothes.
Detailed description of the invention
It is next with reference to the accompanying drawing that invention is further described in detail:
Fig. 1 is the reaction process schematic diagram for preparing the natural weave material that surface modification has aminosilane groups.
Fig. 2 is the reaction process signal for preparing the antimicrobial natural textile material of the surface modification borneol as shown in formula (II)
Figure.
Fig. 3 is the reaction process schematic diagram for preparing the 4- aldehyde benzoic acid borneol derivative.
Fig. 4 is control group: blank cotton fabric and experimental group: the plate of surface of cotton fabric adherent bacteria quantity after borneol modification
Count results comparison diagram.
Fig. 5 is control group: cotton fabric after blank cotton fabric and amino silicone modification, experimental group: cotton is knitted after borneol modification
The antimycotic adhesion effect figure of object macroscopic view (culture 30 days).
Fig. 6 is by control group: blank cotton fabric and experimental group: borneol modifies the rabbit skin of back after cotton fabric acts on
Picture.
Fig. 7 is that borneol modifies the antimycotic adhesion effect figure of cotton fabric (culture 30 days) after 50 circulating water washs.
Specific embodiment
To be readily appreciated that the present invention, the present invention is described more detail below.But before describing the present invention in detail, it should be understood that
The present invention is not limited to the specific embodiments of description.It is also understood that term used herein is only for description specific implementation
Mode, and be not offered as restrictive.
In the case where providing numberical range, it should be understood that in the upper and lower bound of the range and the prescribed limit
Any other regulation or between two parties each of between numerical value numerical value is encompassed by the present invention between two parties.These small range of upper limits
It can independently be included in lesser range with lower limit, and be also covered by the present invention, obey any clear in prescribed limit
The limit of exclusion.Defined range include one or two limit in the case where, exclude any of the limit that those include or
The range of the two is also included in the present invention.
Unless otherwise defined, all terms used herein and those skilled in the art's is usual
Understand meaning having the same.Although similar or equivalent any method and material can also with method described herein and material
To use in implementation or test of the invention, but preferred method and material will now be described.
I. term
Heretofore described term " textile material " refers to fiber and fibre, including fiber, yarn, fabric and its multiple
Close object etc..
Heretofore described term " textile " refers to fibre, and textile fabric is by a kind of production made of processing weaving
Product, including fabric (such as cloth, braided fabric etc.) and its with fiber and/or the compound of yarn etc..
Heretofore described term " kiering " is to utilize caustic soda and other boiling-off additives and pectic substance, waxy substance, nitrogenous
Chemical degradation reaction or emulsification, Swelling Functions etc. occur for substance, cotton seed hulls etc., move back impurity from fabric after washing
It removes.
" water " word used in the present invention refers to deionized water, ultrapure water or distillation in the case where not specifying
Water.
Term of the present invention " optional " " optionally " refers to and selectively adds ingredient, also refers to be added, can also
To be added without.
II. embodiment
As previously mentioned, having plenty of and antibacterial agent being added in textile raw material in the preparation method of existing antibacterial fabric
Anti-bacterial fibre is made, is then woven into various antibiotic fabric products again, this method processing technology difficulty is big, to antibacterial agent requirement
It is high；Have plenty of and antibacterial agent is added during fabrics printing and dyeing final finishing, various antibacterial fabrics are made.There is anti-for this method
Bacterium effect persistence is poor, the poor problem of washability.And then all to there is antibacterial effect not lasting for existing antibacterial agent, washability compared with
The problem of difference, while there is also antibacterial agent releases to cause toxicity, the risk of skin irritation and drug resistance.In consideration of it, this hair
Bright people's antimicrobial natural textile material has carried out a large amount of research.
The present inventor the study found that using surface three-dimensional chemistry new antibacterial strategy, pass through amino silicone be coupled day
Right textile material and 4- aldehyde benzoic acid borneol derivative can prepare a kind of antimicrobial natural textile material, which is a kind of non-
Release type antibacterial textile material, will not bactericide-release kill microorganism, but pass through material surface stereochemical structure shadow
Sticking for microorganism is rung, skin irritatin sensitization will not be caused, skin will not be destroyed and have flora by oneself；The material can effectively muchly
Inhibit sticking for bacterium and fungi, stable structure is water-fastness, and non-toxic, will not lead to drug resistance.The present invention is based on
What above-mentioned discovery was made.
Therefore, the antimicrobial natural textile material of surface modification borneol involved in first aspect present invention is to pass through amino silicone
The natural weave material and 4- aldehyde benzoic acid borneol derivative of oxygen alkane coupling are constituted.
In the present invention, the 4- aldehyde benzoic acid borneol derivative is to be combined by 4- aldehyde benzoic acid and borneol by ester bond
Made of 4- aldehyde benzoic acid borneol acetate, shown in molecular structural formula such as formula (I):
And the structure for constituting the borneol of 4- aldehyde benzoic acid borneol acetate includes D- borneol, L-Borneol and IsoBorneol.
Those skilled in the art will be appreciated that the antimicrobial natural textile material of the surface modification borneol in the present invention is
Using amino silicone as coupling agent, the natural weave material surface that surface has hydroxyl is grafted to by hydrolytic condensation, is assigned
Its surface amino groups is given, then passes through schiff base reaction for 4- aldehyde benzoic acid borneol Derivatives Modified to the textile sheet material with amino
Face, the antimicrobial natural textile material being prepared into also have a characteristic that
(1) for constituting the configuration of the 4- aldehyde benzoic acid borneol derivative of antimicrobial natural textile material in the present invention
Including D- borneol, L-Borneol and IsoOne or more of borneol.
It (2) include three second of 3- aminopropyl for constituting the amino silicone of antimicrobial natural textile material in the present invention
Oxygroup siloxanes, one or more of 3- aminopropyl trimethoxy siloxane and 4- aminobutyl triethoxy siloxanes.
(3) by schiff base reaction that 4- aldehyde benzoic acid is imperial in the antimicrobial natural textile material of surface modification borneol
Brain derived object modifies the natural weave material surface being coupled to amino silicone.
In some embodiments of the invention, for example, the molecular structure such as formula of the antimicrobial natural textile material
(II) shown in:
Those skilled in the art will be appreciated that antimicrobial natural textile material shown in formula (II) only for ease of understanding and
The specific example provided, the structural formula of antimicrobial natural textile material is not limited to that in the present invention.
In the present invention, antimicrobial natural textile material is able to suppress or prevents microorganism adhering in its surface；The microorganism
Including bacterium and/or fungi, including but not limited to one of Escherichia coli, staphylococcus aureus, aspergillus and Mucor or several
Kind.
In some embodiments of the invention, the natural weave material includes cotton fibre material, cotton fiber textile material
One or more of material, flaxen fiber material, flaxen fiber textile material, bamboo fiber material and bamboo fibre fabric material.
The preparation method of the antimicrobial natural textile material of surface modification borneol involved in second aspect of the present invention, including elder generation
Make its surface exposure active amino by the natural weave material that amino silicone is modified, then 4- aldehyde benzoic acid borneol is derivative
Object is modified by the schiff base reaction with surface amino groups, obtains the antimicrobial natural textile material of surface modification borneol, specifically
Preparation method includes:
Natural weave material is placed in amino silicone finishing fluid and carries out immersion treatment, then takes out by step B, heating,
Washing, dries, obtains the natural weave material that surface modification has aminosilane groups；
It is derivative to be placed in 4- aldehyde benzoic acid borneol by step C for the natural weave material that surface modification has aminosilane groups
Immersion treatment is carried out in object finishing fluid, is washed out, dries, and the antimicrobial natural textile material of surface modification borneol is made.
In above-mentioned steps B:
(1) the amino silicone finishing fluid is dissolved in I organic solvent by amino silicone and is formed.Wherein, the I has
Solvent includes toluene and/or acetone；The amino silicone includes 3-aminopropyltriethoxysilane, 3- aminopropyl three
One or more of methoxy silane and 4- ammobutyltriethoxysilane.
(2) in some embodiments of the invention, the content of amino silicone is 5- in the amino silicone finishing fluid
15vol%.
(3) temperature of the immersion treatment is room temperature；The time of the immersion treatment is 10-60min.
(4) temperature of the heating is 50-100 DEG C；The time of the heating is 0.5-3h.
In above-mentioned steps C:
(1) the 4- aldehyde benzoic acid borneol derivative finishing fluid is dissolved in Section II by 4- aldehyde benzoic acid borneol derivative and has
Solvent is formed.Wherein, the Section II organic solvent includes ethyl alcohol, one or more of methanol and acetone；The 4- aldehyde radical
The configuration of benzoic acid borneol derivative includes D- borneol, L-Borneol and IsoOne or more of borneol.
(2) content of 4- aldehyde benzoic acid borneol derivative is in the 4- aldehyde benzoic acid borneol derivative finishing fluid
0.01-0.05g/mL。
(3) temperature of the immersion treatment is room temperature；The time of the immersion treatment is 1-3h.
In some preferred embodiments of the invention, in stepb, it will be placed in by pretreated natural weave material
Immersion treatment is carried out in amino silicone finishing fluid, is then taken out, is heated, and washing is dried, obtaining surface modification has amino silane
The natural weave material of group；
In some further preferred embodiments of the invention, the antimicrobial natural of the above-mentioned surface modification borneol of the present invention is spun
The preparation method for knitting material further includes pretreated step for natural weave material.For natural weave material in the present invention
Preprocess method be not particularly limited, can use natural weave material conventional in the art preprocess method.Example
Such as, it is pre-processed by high temperature scouring.
In some embodiments of the invention, for example, preparing the day that surface modification has aminosilane groups in step B
The reaction schematic diagram of right textile material is as shown in Figure 1.
In other specific embodiments of the invention, for example, preparing surface modification borneol of the invention in step C
The reaction schematic diagram of antimicrobial natural textile material is as shown in Figure 2.
Those skilled in the art will be appreciated that surface modification is prepared in step B shown in Fig. 1 amino silane
The surface modification borneol as shown in formula (II) is prepared shown in the reaction process and Fig. 2 of the natural weave material of group
Antimicrobial natural textile material reaction process and formula (II) shown in surface modification borneol antimicrobial natural textile material only
For the present inventor's specific example providing for ease of understanding, the antimicrobial natural of surface modification borneol is weaved material in the present invention
The structural formula and its reaction process of material are not limited to that.
In some further specific embodiments of the invention, the typical system of antimicrobial natural textile material of the invention
Standby process is as follows:
(1) preparation surface modification has the natural weave material of aminosilane groups: first by pretreated natural textile
Material is immersed in 10-60min in the amino silicone finishing fluid that concentration is 5-15vol%, then takes out in 50-100 DEG C of condition
The lower 0.5-2h that heats finally thoroughly washes off excessive amino silicone, dries, obtaining surface modification has to promote the formation of covalent bond
The natural weave material of aminosilane groups.
(2) it prepares the antimicrobial natural textile material of surface modification borneol: the surface modification that step (1) obtains is had into amino silicone
The natural weave material of groups is immersed in the 4- aldehyde benzoic acid borneol derivative finishing fluid that concentration is 0.01-0.05g/mL
In, 1-3h is impregnated at room temperature.Excessively unbonded 4- aldehyde benzoic acid borneol derivative is finally thoroughly washed away, is dried in the air
It is dry, obtain the antimicrobial natural textile material of surface modification borneol.
The amino silicone described in preferred implementation method of the invention includes 3-aminopropyltriethoxysilane, 3-
TSL 8330 and 4- ammobutyltriethoxysilane.
Amino silicone finishing fluid solvent for use includes toluene and acetone described in preferred implementation method of the invention.
The 4- aldehyde benzoic acid borneol derivative finishing fluid solvent for use packet described in preferred implementation method of the invention
Include ethyl alcohol, methanol and acetone.
The reaction schematic diagram that the 4- aldehyde benzoic acid borneol acetate is prepared in the present invention is as shown in Figure 3.Specific preparation method
It is as follows:
In some embodiments, 1.6mmol4- aldehyde benzoic acid is weighed in reaction flask, and the methylene chloride that 30mL is added mentions
The solvent environment of confession.Then, 0.2mmol4- dimethylamino naphthyridine (DMAP) and 2.0mmol dicyclohexyl are sequentially added thereto
Carbodiimide (DCC) after being completely dissolved, 1mmol borneol is added in above-mentioned system, under room temperature sustained response 12h, is stopped
Crude product is collected after only reacting, crude product is successively filtered by decompression, petroleum ether settles, and is chromatographed and is dried in vacuo finally by column
Target product 4- aldehyde benzoic acid borneol acetate, yield 95% are obtained after equal post-processing steps.The reaction has mild condition, behaviour
Make simple advantage.
In reaction shown in Fig. 3, the borneol includes D- borneol, L-Borneol and IsoOne or more of borneol.
The antimicrobial natural of surface modification borneol involved in third aspect present invention as described in the first aspect of the invention is spun
It is prepared by the antimicrobial natural textile material for knitting the surface modification borneol of material or method preparation as described in respect of the second aspect of the invention
Application in antimicrobial natural textile product.
In some embodiments of the invention, the natural weave material includes cotton fibre material, cotton fiber textile material
One or more of material, flaxen fiber material, flaxen fiber textile material, bamboo fiber material and bamboo fibre fabric material.
In the present invention, antimicrobial natural textile material is able to suppress or prevents microorganism adhering in its surface；The microorganism
Including bacterium and/or fungi, including but not limited to one of Escherichia coli, staphylococcus aureus, aspergillus and Mucor or several
Kind.
Antibacterial or antibacterial test in the present invention is as follows:
Antimycotic experiment: by natural textile material after blank natural weave material (for example, cotton fabric), amino silicone modification
Natural weave material (for example, cotton fabric) is cut into the circle that diameter is 15.0 ± 0.1mm after material (for example, cotton fabric) and borneol modification
Shape sample is flattened on m alt extract agar culture medium after ultraviolet lighting sterilizes 20min.Then, by 10 μ L fungi bacterium solutions
Drop is at center, 30 DEG C of constant temperature incubations, observes and with the growth phenomenon of cameras record different time surrounding materials fungi.
Antibacterium experiment: by natural weave material (example after blank natural weave material (for example, cotton fabric) and borneol modification
Such as, cotton fabric) immerse 107CFU·mL-1Bacterial solution, act on 4h at 37 DEG C.Then three are rinsed with sterile saline
It is secondary, after the bacterium for washing off physical absorption, the bacterium securely sticked on the surface of the material is fallen by ultrasonic cleaning, and distribute it to nothing
In bacterium physiological saline.Finally, 100 μ L dispersion liquids is taken to be coated on nutrient agar, cultivates for 24 hours, carry out flat at 37 DEG C
Plate bacterium colony counts, and calculates antibacterium adherence rate by formula (III):
R (%)=(A-B)/A × 100% (III)
In formula (III):
The antibacterium adherence rate of R- sample；
A- blank natural weave material (for example, cotton fabric) and bacterium solution act on 4h rear surface bacterial adhesion quantity (CFU/
mL)；
Natural weave material (for example, cotton fabric) and bacterium solution act on 4h rear surface bacterial adhesion quantity after the modification of B- borneol
(CFU/mL)。
III. embodiment
The present invention is specifically described below by way of specific embodiment.Experimental method described below, such as without special theory
It is bright, it is laboratory conventional method.Experimental material described below can be obtained unless otherwise instructed by commercial channel.
Embodiment 1:
Pretreated cotton textiles are immersed in the acetone for the 3-aminopropyltriethoxysilane that concentration is 10vol%
10min in solution then takes out and heats 2h under the conditions of 50 DEG C to promote the formation of covalent bond, and last acetone thoroughly washes off excess
Amino silane dries, and obtains the cotton textiles of amino silane modification.Then it is immersed in the D- borneol that concentration is 0.02g/mL
In the ethanol solution of derivative, 1h is impregnated at room temperature.It is derivative that last ethyl alcohol thoroughly washes away excessively unbonded borneol
Object dries, and obtains the cotton textiles of borneol modification.Antibacterium adherence rate is greater than 90%, and antifungic action is greater than 25 days (using real
Test strain: Escherichia coli, staphylococcus aureus, aspergillus, Mucor etc.).
Embodiment 2:
Pretreated cotton textiles are immersed in the acetone for the 3- TSL 8330 that concentration is 10vol%
10min in solution then takes out and heats 2h under the conditions of 60 DEG C to promote the formation of covalent bond, and last acetone thoroughly washes off excess
Amino silane dries, and obtains the cotton textiles of amino silane modification.Then it is immersed in the L-Borneol that concentration is 0.02g/mL
In the ethanol solution of derivative, 2h is impregnated at room temperature.It is derivative that last ethyl alcohol thoroughly washes away excessively unbonded borneol
Object dries, and obtains the cotton textiles of borneol modification.Antibacterium adherence rate is greater than 90%, and antifungic action is greater than 25 days (using real
Test strain: Escherichia coli, staphylococcus aureus, aspergillus, Mucor etc.).
Embodiment 3:
Pretreated cotton textiles are immersed in the toluene for the 3-aminopropyltriethoxysilane that concentration is 5vol%
20min in solution then takes out and heats 1h under the conditions of 70 DEG C to promote the formation of covalent bond, and last toluene thoroughly washes off excess
Amino silane dries, and obtains the cotton textiles of amino silane modification.Then it is immersed in the D- borneol that concentration is 0.01g/mL
In the methanol solution of derivative, 2h is impregnated at room temperature.It is derivative that last methanol thoroughly washes away excessively unbonded borneol
Object dries, and obtains the cotton textiles of borneol modification.Antibacterium adherence rate is greater than 90%, and antifungic action is greater than 25 days (using real
Test strain: Escherichia coli, staphylococcus aureus, aspergillus, Mucor etc.).
Embodiment 4:
Pretreated cotton textiles are immersed in the toluene for the 3- TSL 8330 that concentration is 5vol%
20min in solution then takes out and heats 1h under the conditions of 80 DEG C to promote the formation of covalent bond, and last toluene thoroughly washes off excess
Amino silane dries, and obtains the cotton textiles of amino silane modification.Then it is immersed in the L-Borneol that concentration is 0.01g/mL
In the methanol solution of derivative, 2h is impregnated at room temperature.It is derivative that last methanol thoroughly washes away excessively unbonded borneol
Object dries, and obtains the cotton textiles of borneol modification.Antibacterium adherence rate is greater than 90%, and antifungic action is greater than 25 days (using real
Test strain: Escherichia coli, staphylococcus aureus, aspergillus, Mucor etc.).
Embodiment 5:
Pretreated cotton textiles are immersed in the acetone for the 4- ammobutyltriethoxysilane that concentration is 15vol%
30min in solution then takes out and heats 0.5h under the conditions of 100 DEG C to promote the formation of covalent bond, and last acetone is thoroughly washed off
Excessive amino silane, dries, and obtains the cotton textiles of amino silane modification.Then being immersed in concentration is 0.05g/mL's
In the acetone soln of Iso- borneol derivative, 3h is impregnated at room temperature.Last acetone thoroughly washes away excessively unbonded
Borneol derivative, dries, and obtains the cotton textiles of borneol modification.Antibacterium adherence rate is greater than 95% (Fig. 4), and antifungic action is big
In 30 days (Fig. 5) (using experimental strain: Escherichia coli, staphylococcus aureus, aspergillus, Mucor etc.).
Embodiment 6:
Pretreated cotton textiles are immersed in the acetone for the 3- TSL 8330 that concentration is 15vol%
30min in solution then takes out and heats 1h under the conditions of 100 DEG C to promote the formation of covalent bond, and last acetone was thoroughly washed off
Amino silane is measured, is dried, the cotton textiles of amino silane modification are obtained.Then it is immersed in the D- dragon that concentration is 0.05g/mL
In the acetone soln of brain derived object, 3h is impregnated at room temperature.Last acetone thoroughly washes away excessively unbonded borneol and spreads out
Biology dries, and obtains the cotton textiles of borneol modification.Antibacterium adherence rate is greater than 95%, and antifungic action, which is greater than 30 days, (to be used
Experimental strain: Escherichia coli, staphylococcus aureus, aspergillus, Mucor etc.).
Embodiment 7:
Pretreated cotton textiles are immersed in the acetone for the 3-aminopropyltriethoxysilane that concentration is 15vol%
40min in solution then takes out and heats 0.5h under the conditions of 80 DEG C to promote the formation of covalent bond, and last acetone was thoroughly washed off
Amino silane is measured, is dried, the cotton textiles of amino silane modification are obtained.Then it is immersed in the L- dragon that concentration is 0.05g/mL
In the methanol solution of brain derived object, 3h is impregnated at room temperature.Last methanol thoroughly washes away excessively unbonded borneol and spreads out
Biology dries, and obtains the cotton textiles of borneol modification.Antibacterium adherence rate is greater than 95%, and antifungic action, which is greater than 30 days, (to be used
Experimental strain: Escherichia coli, staphylococcus aureus, aspergillus, Mucor etc.).
Embodiment 8:
Pretreated cotton textiles are immersed in the toluene for the 4- ammobutyltriethoxysilane that concentration is 15vol%
40min in solution then takes out and heats 1h under the conditions of 90 DEG C to promote the formation of covalent bond, and last toluene thoroughly washes off excess
Amino silane dries, and obtains the cotton textiles of amino silane modification.Then it is immersed in the Iso- dragon that concentration is 0.05g/mL
In the methanol solution of brain derived object, 3h is impregnated at room temperature.Last methanol thoroughly washes away excessively unbonded borneol and spreads out
Biology dries, and obtains the cotton textiles of borneol modification.Antibacterium adherence rate is greater than 95%, and antifungic action, which is greater than 30 days, (to be used
Experimental strain: Escherichia coli, staphylococcus aureus, aspergillus, Mucor etc.).
Embodiment 9:
Pretreated cotton textiles are immersed in the toluene for the 4- ammobutyltriethoxysilane that concentration is 15vol%
60min in solution then takes out and heats 1h under the conditions of 100 DEG C to promote the formation of covalent bond, and last toluene was thoroughly washed off
Amino silane is measured, is dried, the cotton textiles of amino silane modification are obtained.Then it is immersed in the L- dragon that concentration is 0.05g/mL
In the ethanol solution of brain derived object, 3h is impregnated at room temperature.Last ethyl alcohol thoroughly washes away excessively unbonded borneol and spreads out
Biology dries, and obtains the cotton textiles of borneol modification.Antibacterium adherence rate is greater than 95%, and antifungic action, which is greater than 30 days, (to be used
Experimental strain: Escherichia coli, staphylococcus aureus, aspergillus, Mucor etc.).
Embodiment 10:
Pretreated cotton textiles are immersed in the acetone for the 4- ammobutyltriethoxysilane that concentration is 10vol%
60min in solution then takes out and heats 3h under the conditions of 100 DEG C to promote the formation of covalent bond, and last acetone was thoroughly washed off
Amino silane is measured, is dried, the cotton textiles of amino silane modification are obtained.Then it is immersed in the D- dragon that concentration is 0.05g/mL
In the ethanol solution of brain derived object, 3h is impregnated at room temperature.Last ethyl alcohol thoroughly washes away excessively unbonded borneol and spreads out
Biology dries, and obtains the cotton textiles of borneol modification.Antibacterium adherence rate is greater than 95%, and antifungic action, which is greater than 30 days, (to be used
Experimental strain: Escherichia coli, staphylococcus aureus, aspergillus, Mucor etc.).Blank cotton fabric and borneol modification after cotton fabric with
After rabbit skin of back effect 6h after shaving, observation is taken pictures afterwards for 24 hours, as shown in fig. 6, skin surface is not formed a scab with redness etc.
Skin irritatin and sensitization phenomenon.Meanwhile the cotton fabric after borneol modification, after 50 circulating water washs, antimycotic adhesion is still
It is able to maintain 30 days (Fig. 7).
It should be noted that embodiment described above for explaining only the invention, is not constituted to of the invention any
Limitation.By referring to exemplary embodiments, invention has been described, it should be appreciated that word used in it is descriptive
With explanatory vocabulary, rather than limited vocabulary.The present invention can be made within the scope of the claims by regulation
Modification, and the present invention is revised in without departing substantially from scope and spirit of the present invention.Although the present invention described in it relates to
And specific method, material and embodiment, it is not intended that the present invention is limited to particular case disclosed in it, on the contrary, this hair
It is bright to can be extended to other all methods and applications with the same function.
Claims (10)
1. a kind of antimicrobial natural textile material of surface modification borneol, the natural weave material that is coupled by amino silicone and
4- aldehyde benzoic acid borneol derivative is constituted.
2. antimicrobial natural textile material according to claim 1, which is characterized in that the 4- aldehyde benzoic acid borneol is derivative
The configuration of object includes one or more of D- borneol, L-Borneol and Iso- borneol；Preferably, the 4- aldehyde benzoic acid borneol
Shown in the molecular structural formula of derivative such as formula (I):
3. antimicrobial natural textile material according to claim 1 or 2, which is characterized in that the amino silicone includes 3-
In aminopropyl triethoxy siloxanes, 3- aminopropyl trimethoxy siloxane and 4- aminobutyl triethoxy siloxanes
It is one or more of；Optionally, in the antimicrobial natural textile material of surface modification borneol, by schiff base reaction by 4- aldehyde radical benzene
The natural weave material surface that formic acid borneol Derivatives Modified is coupled to amino silicone.
4. antimicrobial natural textile material described in any one of -3 according to claim 1, which is characterized in that antimicrobial natural weaving
Material is able to suppress or prevents microorganism adhering in its surface, it is preferable that the microorganism includes bacterium and/or fungi；With/
Or, the natural weave material includes cotton fibre material, cotton fiber textile material, flaxen fiber material, flaxen fiber textile material
One or more of material, bamboo fiber material and bamboo fibre fabric material.
5. a kind of preparation method of the antimicrobial natural textile material of surface modification borneol comprising:
Natural weave material is placed in amino silicone finishing fluid and carries out immersion treatment, then takes out by step B, and heating is washed
It washs, dries, obtain the natural weave material that surface modification has aminosilane groups；
It is whole to be placed in 4- aldehyde benzoic acid borneol derivative by step C for the natural weave material that surface modification has aminosilane groups
Immersion treatment is carried out in reason liquid, is washed out, dries, the antimicrobial natural textile material of surface modification borneol is made.
6. preparation method according to claim 5, which is characterized in that the amino silicone finishing fluid is by amino silicone
I organic solvent is dissolved in be formed；Preferably, the I organic solvent includes toluene and/or acetone；And/or the amino silicone
Oxygen alkane includes 3-aminopropyltriethoxysilane, 3- TSL 8330 and 4- ammobutyltriethoxysilane
One or more of；It is further preferred that the content of amino silicone is 5- in the amino silicone finishing fluid
15vol%.
7. preparation method according to claim 5 or 6, which is characterized in that the 4- aldehyde benzoic acid borneol derivative is whole
Reason liquid is dissolved in Section II organic solvent by 4- aldehyde benzoic acid borneol derivative and is formed；Preferably, the Section II organic solvent includes
One or more of ethyl alcohol, methanol and acetone；And/or the configuration of the 4- aldehyde benzoic acid borneol derivative includes D- dragon
One or more of brain, L-Borneol and Iso- borneol；It is further preferred that the 4- aldehyde benzoic acid borneol derivative arranges
The content of 4- aldehyde benzoic acid borneol derivative is 0.01-0.05g/mL in liquid.
8. the preparation method according to any one of claim 5-7, which is characterized in that in stepb, at the immersion
The temperature of reason is room temperature, and the time of the immersion treatment is 10-60min, and the temperature of the heating is 50-100 DEG C, the heating
Time be 0.5-3h.
9. the preparation method according to any one of claim 5-8, which is characterized in that in step C, at the immersion
The temperature of reason is room temperature, and the time of the immersion treatment is 1-3h.
10. the antimicrobial natural textile material of the surface modification borneol as described in any one of claim 1-4 or as right is wanted
The antimicrobial natural textile material for the surface modification borneol for asking method described in any one of 5-9 to prepare is preparing antimicrobial natural spinning
Knit the application in product；Preferably, the natural weave material includes cotton fibre material, cotton fiber textile material, flaxen fiber
One or more of material, flaxen fiber textile material, bamboo fiber material and bamboo fibre fabric material.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910411303.5A CN110306340B (en) | 2019-05-16 | 2019-05-16 | Antibacterial natural textile material with surface modified borneol and preparation method and application thereof |
| PCT/CN2020/090431 WO2020228808A1 (en) | 2019-05-16 | 2020-05-15 | Borneol surface-modified antimicrobial natural textile material, and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910411303.5A CN110306340B (en) | 2019-05-16 | 2019-05-16 | Antibacterial natural textile material with surface modified borneol and preparation method and application thereof |
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| Publication Number | Publication Date |
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| CN110306340A true CN110306340A (en) | 2019-10-08 |
| CN110306340B CN110306340B (en) | 2020-05-29 |
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| WO (1) | WO2020228808A1 (en) |
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| CN113979894A (en) * | 2021-11-16 | 2022-01-28 | 北京工商大学 | Safe and lasting antibacterial natural textile material and preparation method thereof |
| CN115821588A (en) * | 2022-12-13 | 2023-03-21 | 周权有 | Fabric finishing agent for modal fabric and finishing method |
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| CN113881086B (en) * | 2020-06-17 | 2023-01-24 | 北京化工大学 | Application of non-release antimicrobial adhesion coating in antibacterial building material |
| CN113979894A (en) * | 2021-11-16 | 2022-01-28 | 北京工商大学 | Safe and lasting antibacterial natural textile material and preparation method thereof |
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| CN110306340B (en) | 2020-05-29 |
| WO2020228808A1 (en) | 2020-11-19 |
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