CN108755127A - Chitosan quaternary ammonium salt anti-bacterial fibre and its preparation process - Google Patents
Chitosan quaternary ammonium salt anti-bacterial fibre and its preparation process Download PDFInfo
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- CN108755127A CN108755127A CN201810438113.8A CN201810438113A CN108755127A CN 108755127 A CN108755127 A CN 108755127A CN 201810438113 A CN201810438113 A CN 201810438113A CN 108755127 A CN108755127 A CN 108755127A
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- quaternary ammonium
- ammonium salt
- chitosan
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives thereof
-
- 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
Abstract
Chitosan quaternary ammonium salt anti-bacterial fibre preparation process disclosed by the invention, chitosan and epoxypropyltrimethylchloride chloride are prepared into the chitosan quaternary ammonium salt with degree of substitution, chitosan quaternary ammonium salt is reacted with the closed isocyanates of methyl ethyl ketoxime, obtains reactive chitosan quaternary ammonium salt antimicrobial fluid；Chitosan quaternary ammonium salt antimicrobial fluid impregnates fiber.The invention also discloses the chitosan quaternary ammonium salt anti-bacterial fibres prepared using the above method.It is using the present invention to have synthesized quaternary ammonium salt-modified chitosan and accessed single blocked isocyanate on chitosan：The antibiotic property of this reactive quaternization chitosan is good, significantly larger than chitosan.Chitosan accesses isocyanate reacting group, has good reactivity.Declined by the crystallinity of quaternization chitosan, isocyanates can uniformly be reacted with fabric, and cross-linking effect is good, and anti-microbial property significantly improves, and have wide application prospect.
Description
Technical field
The present invention is application No. is 2016108434101, and the applying date is September in 2016 23, entitled " chitosan quaternary ammonium
The divisional application of the application for a patent for invention of salt anti-bacterial fibre, fabric, amenities and its preparation process ".The present invention relates to one kind
Chitosan anti-bacteria object, more particularly to a kind of concrete application of chitosan quaternary ammonium salt antibacterial.
Background technology
Chitosan (Chitosan) is the product after chitin (Chitin) deacetylation, is that chitin is most basic, most heavy
The derivative wanted.Chitin also known as chitin, chitin, entitled acetamide-2 of (the Isosorbide-5-Nitrae)-2-- deoxidation-β-D-of chemistry
Glucan, be primarily present in the animals such as shrimp, crab, pupa and insect shell and mushroom, algae cell wall in.Arthropods are dynamic
The dry shell of object is containing about 20~50% chitins.There are three types of structures for chitin in nature：α, β, γ, wherein most commonly seen, general
Logical is α types.The biosynthesis amount of annual chitin is billions of tons on the earth, is the natural polymer that yield is only second to cellulose
Sub- compound.The structure of chitin and chitosan is as follows：
In medical industry, the operation suture thread mechanical strength made from chitosan is good, can store for a long time, can use routine side
Method sterilizes, and can be absorbed by the liquid degradation of human body inner tissue, surgical thread need not be removed after wound healing.It is artificial made of chitosan
Skin, has the characteristics that soft, comfortable, and being covered on burn surface can palliate the agonizing sufferings, accelerating wound healing, promote skin regeneration.
Chitosan has many advantages, such as nontoxic, biodegradable, good biocompatibility, makes it in biomaterial, pharmaceutical carrier, medical and agriculture
There are wide research and application prospect in the fields such as industry fungicide, food fresh keeping, environmental protection, veterinary drug and feed addictive, health products.
Therefore how chitosan reaction sexual intercourse is unified into the hot spot for research, the research is related separately to below with reference to data
Hot spot.Toluene di-isocyanate(TDI) cross-linked chitosan is studied the performance of its cross-linking products by An Shengji etc., refers to a peace victory Ji,
The works such as Lan Ying, Zheng Songzhi《Diisocyanate is with chitosan crosslinked product to the absorption property [J] of metal ion》, Changchun science and technology
College journal, 1999,29 (2):197-199.Wei Zhizhen writes《Degradation chitosan and bi-end-blocking isocyanates reactant are in wool
Application [D] on fabric》, Beijing Institute of Clothing Tech, 2005.It is to chitosan and bi-end-blocking isocyanates reaction product in wool fabric
On application, and its finishing effect is discussed using the variation of fabric antistatic property and tensile property after arrangement, passes through orthogonal reality
Test design, it is determined that the best finishing condition of the antistatic property of wool.The patent of invention Shen that Wang Aiguo applies as inventor
Please " a kind of based Wood Adhesives of improvement ", application No. is CN201510186956.X.The application for a patent for invention discloses alum 6-
11 parts, 7-9 parts of disodium ethylene diamine tetraacetate, 5-8 parts of polyvinyl alcohol, 6-10 parts of chitosan, 3-6 parts of stannic chloride, zinc borate 4-9
Part, 7-11 parts of ethyl acetate, 6-8 parts of rosin resin, 3-7 parts of lauryl sodium sulfate, 1-5 parts of sodium sulphate, 3-6 parts of Cortex hibisus syriacus,
7-9 parts of maleic anhydride, 3-10 parts of melamine, 4-10 parts of polyisocyanates, 5-10 parts of butyl acetate.Its timber gluing improved
Agent has good waterproof, the ability of acid and alkali-resistance, while having good viscosity, and adhesiveness is good.Wang little Hua is poly- by shell of degrading
Sugar reacts with isocyanates and prepares antibacterial finishing agent, but author call oneself chitosan and isocyanates can not homogeneous reaction, synthesize
Failure.
The problem of research at present, exists：1, chitosan anti-bacteria is general, need to improve its anti-microbial property.2, chitosan and isocyanic acid
The polarity difference of ester is big, can not be evenly dispersed mutually, causes the general 3. chitosan crystallinity of crosslinking agent reunion cross-linking properties strong, such as
Fruit does not break its crystallinity, and then often crosslinking only occurs in chitosan dispersed phase in crosslinking agent dispersed phase interface, can not go deep into solid
It is fixed.
Invention content
In view of this, the purpose of the present invention is to provide a kind of chitosan quaternary ammoniums that can improve cross-linking effect and anti-microbial property
Salt anti-bacterial fibre preparation process.
The present invention also provides a kind of chitosan quaternary ammonium salt anti-bacterial fibres that can improve cross-linking effect and anti-microbial property.
In order to achieve the above objectives, solution of the invention is：
Chitosan quaternary ammonium salt anti-bacterial fibre preparation process, is realized by following steps：By chitosan and glycidyl front three
Ammonium chloride is prepared into the chitosan quaternary ammonium salt with degree of substitution, then by the closed isocyanide of chitosan quaternary ammonium salt methyl ethyl ketoxime
Acid esters reacts, you can obtains reactive chitosan quaternary ammonium salt antimicrobial fluid；Chitosan quaternary ammonium salt antimicrobial fluid impregnates fiber.
The ratio between the chitosan and the mass parts of the epoxypropyltrimethylchloride chloride substance are 1：3-4, reaction temperature
It it is 70-80 DEG C, the reaction time is 5-8 hours.
It after the reactant of the chitosan and the epoxypropyltrimethylchloride chloride filters, is cleaned through ethyl alcohol, drying life
It is reacted at product two, then with the closed isocyanates of the methyl ethyl ketoxime.
Dry butanone is added in the methyl ethyl ketoxime, is then slowly dropped in isophorone diisocyanate, then delays
Slowly 80 DEG C are warming up to, are cooled to room temperature and generate product one, then is reacted with the chitosan quaternary ammonium salt.
In a dropping step, the ratio between active hydrogen and the amount of substance of-NCO are n (H)：N (NCO)=0.55：1, temperature is added dropwise
Degree is no more than 40 DEG C.
The product two is dissolved in generation product three in dry dimethyl sulfoxide (DMSO), by the closed isocyanates of the methyl ethyl ketoxime
It is injected into the product three, the ratio between mass parts are：The closed isocyanates of methyl ethyl ketoxime：Two=2-8 of product：100.
The closed isocyanates of methyl ethyl ketoxime is reacted with the product three, after being stirred at room temperature 3 hours, through first
Alcohol precipitates, you can obtains the reactive chitosan quaternary ammonium salt antimicrobial fluid.
Chitosan quaternary ammonium salt anti-bacterial fibre is made using foregoing any technique.
After adopting the above scheme, the invention has the advantages that：The quaternary ammonium salt-modified shell that synthesized of the present invention gathers
Sugar simultaneously accesses single blocked isocyanate on chitosan：1, the antibiotic property of this reactive quaternization chitosan is good, much high
In chitosan.2, chitosan accesses isocyanate reacting group, has good reactivity.3, pass through quaternization chitosan
Crystallinity declines, and isocyanates can uniformly be reacted with fabric, and cross-linking effect is good, and anti-microbial property significantly improves.
Specific implementation mode
In order to further explain the technical solution of the present invention, being explained in detail the present invention below by specific embodiment
It states.
Chitosan quaternary ammonium salt antibacterial (abbreviation antibacterial) mainly include chitosan quaternary ammonium salt antiseptic (abbreviation antiseptic),
Chitosan quaternary ammonium salt antimicrobial fluid (abbreviation antimicrobial fluid), and with antiseptic, antimicrobial fluid impregnate gained anti-bacterial fibre, fabric, defend
Raw articles for use, such as：Towel, underwear, socks, sanitary napkin, mask, bandage etc..
Illustrate by taking chitosan quaternary ammonium salt antiseptic as an example below, the present invention is by chitosan and epoxypropyltrimethylchloride chloride
It is prepared into the chitosan quaternary ammonium salt with certain degree of substitution, then reacts it with the closed isocyanates of methyl ethyl ketoxime,
Reactive chitosan quaternary ammonium salt antiseptic can be obtained.
Wherein, degree of substitution refers to attack of the organic compound by certain class reagent, makes in molecule a base or atom by this
The reaction that a reagent is replaced.Substitution reaction can be divided into nucleophilic displacement of fluorine, parental materials and homolysis substitution three classes.If substitution reaction
Occur in the molecule between each group, referred to as Intramolecular substitution.Molecular rearrangement occurs simultaneously again in some substitution reactions, such as resets
Reaction.
Embodiment one
1, methyl ethyl ketoxime is added to dry butanone, be then slowly dropped in isophorone diisocyanate.Preferably,
The ratio for controlling active hydrogen and the mass parts of-NCO is n (H)：N (NCO)=0.55：1, dropping temperature is controlled no more than 40 DEG C, and
After be to slowly warm up to 80 DEG C, it is cooling, in case reaction is used at room temperature below.Product in the step can be referred to as product one, lead to
Its extent of reaction can be measured by crossing di-n-butylamine method.
2,100ml isopropanols, 5 grams of chitosans and appropriate epoxypropyltrimethylchloride chloride are added in three-necked bottle.Preferably
Ground, the ratio between control chitosan and the mass parts of epoxypropyltrimethylchloride chloride substance are 1：3-4,70-80 DEG C of reaction temperature, when
Between 5-8 hours, then can filter, with ethyl alcohol fully clean, drying.Product in the step can be referred to as product two.Certainly
If it is needing to be prepared into liquid, ethyl alcohol is removed, drying can be saved.
3, the product two in aforementioned 2nd article is dissolved in dry dimethyl sulfoxide (DMSO) (DMSO) and generates product three, it then will be in 1
Product one be injected into the product three in 3.Preferably, the ratio between mass parts are：W (product one)：W (product two)=2-8：100.?
It stirs at room temperature 3 hours, it is dry then with a large amount of methanol extractions, you can to obtain reactive chitosan quaternary ammonium salt antiseptic.Certainly such as
Fruit needs to be prepared into liquid, removes methanol, can save drying.
Embodiment two
The present embodiment and the main distinction of embodiment one are that chitosan quaternary ammonium salt antibacterial is liquid, i.e. chitosan
Quaternary ammonium salt antimicrobial fluid.Chitosan quaternary ammonium salt antibacterial liquid preparing process can be used be prepared into antiseptic such as the technique of embodiment one after,
Again according to a conventional method, such as soluble in water, stirring can be made into the chitosan quaternary ammonium salt antimicrobial fluid of liquid.In addition, chitosan season
The technique in embodiment one also can be used in ammonium salt antimicrobial fluid, only correspondingly saves the step of moisture content is sloughed in drying, drying etc. i.e.
It can.Other same place, details are not described herein.
Embodiment three
The present embodiment is one of the concrete application of embodiment one.By the chitosan quaternary ammonium salt antiseptic (abbreviation antiseptic),
Soluble in water, stirring, antiseptic is impregnated with the ratio of cloth weight 0.1-1%, the ratio of bath raio 7-10, dehydration, 90 DEG C of drying, and 120
DEG C bake 30 minutes, you can chitosan quaternary ammonium salt antibiotic fabric (abbreviation antibiotic fabric).Preferably, material is completely soaked, leaching
Steep half an hour or several hours.Anti-microbial Performance Tests are carried out with FZ73023 standards, are washed 50 times, Escherichia coli bacteriostasis rate is as follows：
| Sample number into spectrum | 1 | 2 | 3 |
| Antibiotic rate | 55.42 | 67.44 | 99.99 |
Sample 1 is chitosan and commercially available closure isocyanates Beyer Co., Ltd 3100；Sample 2 is chitosan without step
2 quaternization, directly closes monoisocyanates by chitosan graft；Sample 3 is quaternization chitosan of the present invention, i.e.,
Chitosan quaternary ammonium salt antiseptic, anti-microbial property greatly improve.
Example IV
The present embodiment is the further expansion application of embodiment three.Utilize chitosan quaternary ammonium salt antiseptic, antiseptic
Liquid can by fiber, fabric, amenities, such as：The materials such as towel, underwear, socks, sanitary napkin, mask, bandage, in use
Prepared by the technique stated in embodiment three, to which correspondence is prepared into following antibacterial：Anti-bacterial fibre, antibiotic fabric, Antimicrobial sanitation
Articles for use, such as：Antibacterial towel, antibacterial underwear, antimicrobial socks, antibacterial sanitary napkin, antibacterial mask, antibacterial bandage etc..
Specifically, antiseptic weighs 0.1 ± 0.06-1 ± 0.5% ratio, the i.e. weight of antiseptic and material with material
Than being 0.1 ± 0.06-1 ± 0.5%, such as 0.04%, 0.5%, 1.06%, 1.1%, 1.2%, 1.5%, bath raio 7-10's
Ratio is impregnated, dehydration, 65-100 DEG C of drying, such as 65 DEG C, 70 DEG C, 75 DEG C, 80 DEG C, 85 DEG C, 90 DEG C, 100 DEG C of drying, 120 ±
10 degree bake 30 ± 15 minutes, and sizing treatment etc. can obtain chitosan quaternary ammonium salt antibiotic fabric (abbreviation antibiotic fabric).Certainly anti-
Microbial inoculum can also be substituted by antimicrobial fluid, and antibiotic fabric is also alternatively at anti-bacterial fibre, amenities.
The product form and style of above-described embodiment and the non-limiting present invention, the ordinary skill people of any technical field
The appropriate changes or modifications that member does it all should be regarded as the patent category for not departing from the present invention.
Claims (8)
1. chitosan quaternary ammonium salt anti-bacterial fibre preparation process, which is characterized in that realized by following steps：By chitosan and epoxy
Hydroxypropyltrimonium chloride is prepared into the chitosan quaternary ammonium salt with degree of substitution, then seals chitosan quaternary ammonium salt with methyl ethyl ketoxime
The isocyanates closed reacts, you can obtains reactive chitosan quaternary ammonium salt antimicrobial fluid；Chitosan quaternary ammonium salt antimicrobial fluid is impregnated fine
Dimension.
2. chitosan quaternary ammonium salt anti-bacterial fibre preparation process as described in claim 1, which is characterized in that the chitosan and institute
It is 1 to state the ratio between mass parts of epoxypropyltrimethylchloride chloride substance：3-4, reaction temperature are 70-80 DEG C, reaction time 5-8
Hour.
3. chitosan quaternary ammonium salt anti-bacterial fibre preparation process as described in claim 1, which is characterized in that the chitosan and institute
State epoxypropyltrimethylchloride chloride reactant filter after, through ethyl alcohol clean, drying generate product two, then with the methyl ethyl ketone
The closed isocyanates of oxime is reacted.
4. chitosan quaternary ammonium salt anti-bacterial fibre preparation process as described in claim 1, which is characterized in that the methyl ethyl ketoxime adds
Enter dry butanone, be then slowly dropped in isophorone diisocyanate, is then to slowly warm up to 80 DEG C, is cooled to room temperature
Product one is generated, then is reacted with the chitosan quaternary ammonium salt.
5. chitosan quaternary ammonium salt anti-bacterial fibre preparation process as claimed in claim 4, which is characterized in that a dropping step
In, the ratio between active hydrogen and the amount of substance of-NCO are n (H)：N (NCO)=0.55：1, dropping temperature is no more than 40 DEG C.
6. chitosan quaternary ammonium salt anti-bacterial fibre preparation process as claimed in claim 3, which is characterized in that the product two is dissolved in
Product three is generated in dry dimethyl sulfoxide (DMSO), the closed isocyanates of the methyl ethyl ketoxime is injected into the product three, matter
Measuring the ratio between part is：The closed isocyanates of methyl ethyl ketoxime：Two=2-8 of product：100.
7. chitosan quaternary ammonium salt anti-bacterial fibre preparation process as claimed in claim 6, which is characterized in that the methyl ethyl ketoxime envelope
The isocyanates closed is reacted with the product three, after being stirred at room temperature 3 hours, through methanol extraction, you can obtains the reaction
Property chitosan quaternary ammonium salt antimicrobial fluid.
8. chitosan quaternary ammonium salt anti-bacterial fibre, which is characterized in that be made using any technique in such as claim 1 to 7.
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| CN201810437116.XA Active CN108503727B (en) | 2016-09-23 | 2016-09-23 | Chitosan quaternary ammonium salt antibacterial fabric, sanitary product and preparation process thereof |
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| CN111041829A (en) * | 2019-12-30 | 2020-04-21 | 华侨大学 | Preparation method of reactive chitosan-based fabric antibacterial agent |
| CN111519343A (en) * | 2020-03-02 | 2020-08-11 | 上海东喜实业有限公司 | Manufacturing method of high-tear high-strength needle-punched non-woven fabric for synthetic leather |
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| CN111041829B (en) * | 2019-12-30 | 2023-08-25 | 华侨大学 | Preparation method of reactive chitosan-based fabric antibacterial agent |
| CN111519343A (en) * | 2020-03-02 | 2020-08-11 | 上海东喜实业有限公司 | Manufacturing method of high-tear high-strength needle-punched non-woven fabric for synthetic leather |
| CN114456280A (en) * | 2022-02-24 | 2022-05-10 | 上海科汭新材料有限责任公司 | Modified chitosan, preparation method and application thereof |
| CN114456280B (en) * | 2022-02-24 | 2022-12-20 | 上海科汭新材料有限责任公司 | Modified chitosan, preparation method and application thereof |
Also Published As
| Publication number | Publication date |
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| CN108503727B (en) | 2021-02-26 |
| CN108503727A (en) | 2018-09-07 |
| CN108755127B (en) | 2021-02-26 |
| CN106436313A (en) | 2017-02-22 |
| CN106436313B (en) | 2018-10-12 |
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