CN105461814B - A kind of cellulose acetate derivative and its production and use - Google Patents
A kind of cellulose acetate derivative and its production and use Download PDFInfo
- Publication number
- CN105461814B CN105461814B CN201510926078.0A CN201510926078A CN105461814B CN 105461814 B CN105461814 B CN 105461814B CN 201510926078 A CN201510926078 A CN 201510926078A CN 105461814 B CN105461814 B CN 105461814B
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- CN
- China
- Prior art keywords
- cellulose acetate
- ether
- organic solvent
- triclosan
- acetic acid
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B13/00—Preparation of cellulose ether-esters
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
Abstract
The invention provides a kind of cellulose acetate derivative, its structural formula are as follows：
Description
Technical field
The invention belongs to high polymer material and chemical field, is related to a kind of cellulose acetate, specifically a kind of acetic acid
Cellulose derivative and its production and use.
Background technology
Triclosan, chemical name Irgacare MP.2,4,4 '-three chloro- 2 '-dihydroxy diphenyl ethers are
A kind of bactericide and bacteriostatic agent of 1980s exploitation, because it is to gram-positive bacteria, Gram-negative bacteria, ferment
Female and virus, antibiotic bacterium, non-antibiotic bacterium etc. are respectively provided with efficient killing and inhibitory action, while have and be not infected with production extensively
Product and skin, without a variety of outstanding advantages such as any penetrating odor, harmless to human body and Environmental security, therefore be widely used as efficiently
Medicated soap, sanitary perfumed soap, hygienic body lotion, toothpaste mouthwash, cosmetics, mildy wash, air freshener, wound and medical apparatus sterilizing
The bactericidal active ingredient of agent, fabric and leather sanitary finish agent etc..
Triclosan is initially developed and produced by Ciba-Geigy companies of Switzerland, and existing oneself by FDA certifications and is put into Europe and be total to
In effective preservative register of body cosmetics guide.
The sterilization mechanism of triclosan be by blocking the aliphatic acid of bacterium to synthesize what is realized, triclosan by analogue enztme from
Right substrate specificity inactivates enzyme, is the enzyme inhibitor of active particle directive property.
Triclosan is kind of a nonspecific broad-spectrum bactericidal action, and it has the characteristics that efficient, holding effect and low toxicity characteristic.It is existing
In technology, antibiotic facing material has been widely used in clothes, but antibiotic facing material of the prior art is general all in fabric table
Face is using dipping or spray antimicrobial agent, the not wash resistant of the antibiotic facing material through so handling, and antibacterial is lost after washing for several times and is made
With.
The content of the invention
It is an object of the invention to provide a kind of cellulose acetate derivative and its production and use, described is this
Cellulose acetate derivative and its production and use will solve anti-biotic material of the prior art in the application, antibacterial action
The technical problem for gradually reducing and disappearing after scrubbed.
The invention provides a kind of cellulose acetate derivative, its structural formula are as follows：
Present invention also offers a kind of preparation method of above-mentioned cellulose acetate derivative, comprise the following steps：
1) the step of preparation 2 ', 4 ', 4- tri- chloro- 2- [(α-acetic acid) ether]-diphenyl ether；Weigh triclosan phenol sodium and α-
Monoxone, described triclosan phenol sodium are 0.8 with α-monoxone mol ratio:0.8~1.2, by triclosan phenol sodium and α-monoxone
In organic solvent, the mass volume ratio of described triclosan phenol sodium and organic solvent is 1g for dissolving:1.5~50ml；Described
The mass volume ratio of monoxone and organic solvent is 100g:100~250ml；By triclosan sodium phenolate solution and α-chloroacetic acid solution
Mixing, is reacted at a temperature of 35~50 DEG C, and the reaction time is 60~150 minutes；Above-mentioned reaction solution is poured into frozen water
In, stratification is stirred, divides after removing water and dries；After dried liquid pressure-reducing, colourless liquid 2 ', 4 ', tri- chloro- 2- of 4- are obtained
[(α-acetic acid) ether]-diphenyl ether；
2) cellulose acetate is weighed, described cellulose acetate dissolving is dissolved by heating in organic solvent, described vinegar
The mass volume ratio of acid cellulose and organic solvent is 100g:400~900ml；Then it is added dropwise and is dissolved in above-mentioned solution
Tri- chloro- 2- of 2 ' in organic solvent, 4 ', 4- [(α-acetic acid) ether]-diphenyl ether, described (chloro- the 2- [(α-second of 2 ', 4 ', 4- tri-
Acid) ether]-diphenyl ether) and the mass volume ratio of organic solvent be 1g:2~50ml；1- (the 3- diformazans of catalytic amount are added dropwise simultaneously
Aminopropyl) -3- ethyl carbodiimides and DMAP, described 1- (3- dimethylamino-propyls) -3- ethyls carbon two
Imines and DMAP are dissolved into organic solvent, and described 1- (3- dimethylamino-propyls) -3- ethyls carbon two is sub-
The mass volume ratio 30g of amine (EDC) and organic solvent：50~150ml；Described DMAP (DMAP) and organic molten
The mass volume ratio 1g of agent：4~10ml；Reacted under conditions of being 35~50 DEG C in temperature, 4~8 hours reaction time, so
Reactant mixture is poured into PH afterwards<In 3 acid frozen water, divide and remove upper water, liquid of the lower floor containing reactant carries out depressurizing in vain
Color solids, white solid thing are dissolved with dioxane, and liquid pouring separates out target product 2 ' into deionized water after dissolving,
4 ', 4- trichlorine (- 2- [(cellulose acetate) ether]-diphenyl ether.
Further, cellulose acetate, 2 ', 4 ', 4-, tri- chloro- 2- [(α-acetic acid) ether]-diphenyl ether, catalyst (1- (3- bis-
Methylaminopropyl) -3- ethyl carbodiimides and DMAP) mol ratio be 0.8:1~1.2：0.8~1.2.
Further, described organic solvent is chloroform, acetone, dioxane, dimethylformamide or two chloroethenes
Alkane.
Specifically, 1- (3- dimethylamino-propyls) -3- ethyl carbodiimides (EDC) and DMAP (DMAP)
Mass ratio is 25~35：1.
Specifically, the frozen water containing acid refers to PH<The ice water solution of 3 acetic acid, hydrochloric acid or sulfuric acid.
Present invention also offers a kind of purposes of the above-mentioned cellulose acetate derivative in antibiotic facing material is prepared.
The present invention has synthesized a kind of cellulose acetate derivative with antibacterial activity group -- the vinegar containing " triclosan "
Sour fiber.
The reaction equation of the present invention is as follows：
If the reaction condition of the present invention is by the well-known method that routinizes, using catalysis of the concentrated sulfuric acid as esterification
Agent, this catalyst can not be realized to the target of this experiment.Urged according to DCC (N, N '-dicyclohexylcarbodiimide)
Change, then reaction must first do the Acibenzolar obtained after esterification to this compound of reaction (A) and could exist with Triafol T
Reacted under DCC catalysis, which increase cost of manufacture, and a large amount of discarded objects can be also produced in synthesis, add discarded object
Handle work.
The present invention reacts (catalyst using the direct esterification of compound (A):EDC+DMAP), it the advantages of be reaction condition
Gently, cost of manufacture is relatively cheap, the recyclable recycling of catalyst.
The present invention compares with prior art, and its technological progress is significant.Present invention utilizes the phenolic hydroxyl group of triclosan
Esterification characteristic is combined with Triafol T, does not change the antibacterial characteristics of triclosan.Using Triafol T and triclosan
With reference to, it is shown that its antibacterial activity, the advantages of it is most significantly unique is to be used continuously with forward osmosis membrane of its making for a long time
In will not progressively weaken and lose its anti-microbial property.
Embodiment
Embodiment 12 ', the synthesis of 4 ', 4-, tri- chloro- 2- [(α-acetic acid) ether]-diphenyl ether
At one equipped with 1 liter of glass reaction bottle of reflux condensing tube, thermometer, mechanical agitator and constant pressure funnel
251.5 grams of triclosan phenol sodium and 400ml chloroforms are firstly added, starts stirring, room-temperature dissolution is uniform, and chloroethene is then slowly added dropwise
Sour 99.3 grams/chloroform 200ml, reaction temperature are maintained at less than 50 DEG C, are added dropwise, and temperature does not continue reaction 120 to reaction condition
Minute, the reaction solution is poured into frozen water stratification point after (deionized water) stirs 10 minutes and removes water after reaction terminates, then uses ice
Water washing once divides after water the solution to filter out magnesium sulfate after being dehydrated with anhydrous magnesium sulfate afterwards, liquid pressure-reducing (50 DEG C/
Cooling water in condenser pipe 10mmHg) is changed into more than 50 DEG C of water (because product fusing point is higher) after removing chloroform, continues to be warming up to
95 DEG C/5mmHg, collect product and obtain colourless liquid, product yield 94%, the liquid stands heat release and separates out acicular crystal, 59 DEG C of fusing point.
Embodiment 22 ', the synthesis of 4 ', 4-, tri- chloro- 2- [(cellulose acetate) ether]-diphenyl ether
Chloroform is added in 1 liter of glass reaction bottle equipped with condenser pipe, thermometer, constant pressure funnel and agitator
400ml, cellulose acetate (C6H7O2(OOCCH3) n (n=1~3)) 57.6g, start and stir and be heated to reflux to acetate fiber
Element starts that compound A { (tri- chloro- 2- of 2 ', 4 ', 4- [(α-acetic acid) ether]-diphenyl ether)/chloroform 68g/ are added dropwise after being completely dissolved
150ml }, while 1- (3- dimethylamino-propyls) -3- ethyl carbodiimides (EDC) 30g/ chloroform 150ml and 4- diformazan ammonia is added dropwise
Yl pyridines (DMAP) 1g/5ml chloroforms, 50 DEG C of reaction temperature, it is added dropwise and continues reaction 6 hours, reaction reacts mixing after terminating
Thing is poured into containing standing 5 minutes after being stirred 10 minutes in sour frozen water, is divided and is removed upper water, lower floor is depressurized containing reactant and chloroform
Distillation adds dioxane stirring and dissolving after removing chloroform, and liquid is poured into analysis object 2 ', 4 ', 4-2- in deionized water after dissolving
[(cellulose acetate) ether]-diphenyl ether white crystal 110g.
The suppression sterilization evaluation test of embodiment 3
5 grams of Triafol Ts being esterified through triclosan phenolic hydroxyl group are taken, separately take 5 grams of Triafol Ts or diacetate fiber
Element (1:1) mix, or directly take the Triafol T that 5 grams of triclosan phenolic hydroxyl groups are esterified, with acetone, dimethyl acetamide,
The organic solvents such as 1-METHYLPYRROLIDONE, acetic acid are dissolved to flowable mucus, topple over a small amount of mucus respectively in cleaned glass plate
On, be bulldozed mucus film forming with padded 0.3mm glass bar, glass plate be put into deionization basin one hour, gently by film from
Peeled off on glass plate, change deionized water and diaphragm is continued into rinsing four to six hours, pull diaphragm out from water and shakeout and totally filtering
On paper, put 65 degree of baking ovens and dry two hours (dry and sterilize).Taken out and be placed in sterile stainless steel box with aseptic nipper.In sterile bar
It is under part that diaphragm sub-cut is standby into diameter 10x10mm small pieces.A part of diaphragm is separately taken to be placed on a large amount of (1000ml) 30 DEG C of warm water
Middle agitation, simulation washing, often wash one hour and take a part of sample to be dried for standby, and change warm water, change warm water altogether 10 times, mould
Intend ten washings, with influence of the observation washing to fungistatic effect.
By health ministry 2002 editions《Disinfection technology standard》And GB/T20944.2-2007《Antibacterial textile performance is commented
Valency》Method to made from synthesis diaphragm carry out bacteriostasis property evaluation.Select staphylococcus aureus ATCC6538, Escherichia coli
8099 be used as representative strains, by standard method in soy peptone meat soup by actication of culture, be transferred to soy peptone agar
Cultivated in medium slant test tube, 1x10 is made into 100ml soybean protein meat soups with oese picking strain5CFU/ml~
3x105The bacterium solution of CFU/ml concentration, 0.1ml bacterium solutions drop coating is taken to be contaminated on foregoing manufactured diaphragm with sterilizing quantitative liquid shifter
Bacterium small pieces are placed in sterile vials, cover culture 18~24 hours in rearmounted 370 insulating box, while separately take some commercially available 0.1mm
Thick polyester piece does control group, and bacterium solution culture is inoculated with after same sterilizing.Two groups of experiment bottles are opened after 18~24 hours, are separately added into
20ml SCDLP fluid nutrient mediums, vibration, which is rocked 30 seconds, elutes the bacterium solution contaminated on diaphragm, and 1ml is taken respectively with pipettor
Eluent is added in the test tube of the sterilized fluid nutrient medium containing 9mlSCDLP, and by 1:10 ratios do the dilution of three gradients.
1ml liquid is taken uniformly to be poured over the dish surface for counting culture medium containing EA in each test tube, plate is placed in 370 insulating boxs and trained
Support 24 hours, visually observe counting.
SCDLP fluid nutrient mediums:
EA counts culture medium:
As a result：
1:1 pair half dilutes and does not dilute diaphragm made of the pure Triafol T through the esterification of triclosan phenolic hydroxyl group to each
Without colony growth after the bacterium solution culture of individual concentration；Colony growth number is equal after control group polyester flake culture>100CFU.
The Triafol T through the esterification of triclosan phenolic hydroxyl group of the present invention has extremely good in terms of evaluation experimental result
Anti- bacteriostasis property, bacteriostasis property is unchanged after ten washings, has illustrated the Triafol T through the esterification of triclosan phenolic hydroxyl group
Grafting has synthesized triclosan on cellulose acetate securely, and the cellulose acetate for generating a kind of group containing antibacterial activity derives
Thing -- the acetate fiber containing " triclosan ", it has the anti-microbial property similar to triclosan, and extremely resistance to cleaning washing.
Claims (6)
1. a kind of preparation method of cellulose acetate derivative, it is characterised in that comprise the following steps：
1) the step of preparation 2 ', 4 ', 4- tri- chloro- 2- [(α-acetic acid) ether]-diphenyl ether；Weigh triclosan phenol sodium and α-chloroethene
Acid, described triclosan phenol sodium are 0.8 with α-monoxone mol ratio:0.8~1.2, triclosan phenol sodium and α-monoxone are dissolved
In organic solvent, the mass volume ratio of described triclosan phenol sodium and organic solvent is 1g:1.5~50ml；Described chloroethene
The mass volume ratio of acid and organic solvent is 100g:100~250ml；Triclosan sodium phenolate solution and α-chloroacetic acid solution are mixed,
Reacted at a temperature of 35~50 DEG C, the reaction time is 60~150 minutes；Above-mentioned reaction solution is poured into frozen water, stirred
Stratification is mixed, divides after removing water and dries；After dried liquid pressure-reducing, colourless liquid 2 ', 4 ' is obtained, tri- chloro- 2- of 4- [(α-
Acetic acid) ether]-diphenyl ether；
2) cellulose acetate is weighed, described cellulose acetate dissolving is dissolved by heating in organic solvent, described acetic acid is fine
The mass volume ratio of dimension element and organic solvent is 100g:400~900ml；Then in above-mentioned solution be added dropwise be dissolved in it is organic
Tri- chloro- 2- of 2 ' in solvent, 4 ', 4- [(α-acetic acid) ether]-diphenyl ether, described 2 ', 4 ', 4-, tri- chloro- 2- [(α-acetic acid) ether]-
The mass volume ratio of diphenyl ether and organic solvent is 1g:2~50ml；1- (the 3- dimethylaminos third of catalytic amount are added dropwise simultaneously
Base) -3- ethyl carbodiimides and DMAP, described 1- (3- dimethylamino-propyls) -3- ethyl carbodiimides and
DMAP dissolves in organic solvent respectively, described 1- (3- dimethylamino-propyls) -3- ethyl carbodiimides and
The mass volume ratio 30g of organic solvent：50~150ml；Described DMAP and the mass volume ratio of organic solvent
1g：4~10ml；Reacted under conditions of being 35~50 DEG C in temperature, 4~8 hours reaction time, then by reactant mixture
It is poured into pH<In 3 acid frozen water, divide and remove upper water, liquid of the lower floor containing reactant carries out depressurizing to obtain white solid thing, and white is solid
Body thing is dissolved with dioxane, and liquid pouring separates out target product 2 ', 4 ', 4- trichlorines (- 2- into deionized water after dissolving
[(cellulose acetate) ether]-diphenyl ether.
A kind of 2. preparation method of cellulose acetate derivative according to claim 1, it is characterised in that：Acetate fiber
The mol ratio of element, 2 ', 4 ', 4-, tri- chloro- 2- [(α-acetic acid) ether]-diphenyl ether and catalyst is 0.8:1~1.2：0.8~1.2, institute
The catalyst stated is 1- (3- dimethylamino-propyls) -3- ethyl carbodiimides and DMAP.
A kind of 3. preparation method of cellulose acetate derivative according to claim 1, it is characterised in that：Described is organic
Solvent is chloroform, acetone, dioxane, dimethylformamide or dichloroethanes.
A kind of 4. preparation method of cellulose acetate derivative according to claim 1, it is characterised in that：1- (3- diformazans
Aminopropyl) mass ratio of -3- ethyl carbodiimides and DMAP is 25~35：1.
A kind of 5. preparation method of cellulose acetate derivative according to claim 1, it is characterised in that：Described acidity
Frozen water refers to pH<The ice water solution of 3 acetic acid, hydrochloric acid or sulfuric acid.
A kind of 6. purposes of the cellulose acetate derivative prepared using the method for claim 1 in anti-biotic material is prepared.
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| CN201510926078.0A CN105461814B (en) | 2015-12-14 | 2015-12-14 | A kind of cellulose acetate derivative and its production and use |
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| CN201510926078.0A CN105461814B (en) | 2015-12-14 | 2015-12-14 | A kind of cellulose acetate derivative and its production and use |
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| CN105461814B true CN105461814B (en) | 2018-03-27 |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107417795B (en) * | 2017-09-05 | 2020-06-05 | 南通醋酸纤维有限公司 | Cellulose acetate sorbate and preparation method and application thereof |
| CN110438795A (en) * | 2019-08-20 | 2019-11-12 | 浙江新派服饰有限公司 | A kind of radiation protection antibacterial fabric |
| CN110356059B (en) * | 2019-08-20 | 2021-06-08 | 浙江仁派服饰有限公司 | Antibacterial ultraviolet-proof fabric |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1297499A (en) * | 1998-02-20 | 2001-05-30 | 美利肯研究公司 | Esterified triclosan derivs. as improved textile antimicrobial agent |
| CN1400355A (en) * | 2002-09-20 | 2003-03-05 | 清华大学 | Preparation method of macromolecular sterilization fibre with grafted antibacterial monomer on its surface |
| CN101871167A (en) * | 2010-06-29 | 2010-10-27 | 常州大学 | Preparation method of antibacterial cellulose fabric |
| CN103422339A (en) * | 2013-08-23 | 2013-12-04 | 华南理工大学 | Method for preparing antibacterial functional cellulosic fibers |
| CN103787997A (en) * | 2014-02-18 | 2014-05-14 | 江南大学 | Reaction type antibacterial agent as well as synthetic method and application thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000045179A (en) * | 1998-07-23 | 2000-02-15 | Toyobo Co Ltd | Antimicrobial fiber and its fibrous structure |
| US20040185250A1 (en) * | 2003-02-07 | 2004-09-23 | John Amy T. | Triclosan containing absorbable sutures with extended antimicrobial properties |
-
2015
- 2015-12-14 CN CN201510926078.0A patent/CN105461814B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1297499A (en) * | 1998-02-20 | 2001-05-30 | 美利肯研究公司 | Esterified triclosan derivs. as improved textile antimicrobial agent |
| CN1400355A (en) * | 2002-09-20 | 2003-03-05 | 清华大学 | Preparation method of macromolecular sterilization fibre with grafted antibacterial monomer on its surface |
| CN101871167A (en) * | 2010-06-29 | 2010-10-27 | 常州大学 | Preparation method of antibacterial cellulose fabric |
| CN103422339A (en) * | 2013-08-23 | 2013-12-04 | 华南理工大学 | Method for preparing antibacterial functional cellulosic fibers |
| CN103787997A (en) * | 2014-02-18 | 2014-05-14 | 江南大学 | Reaction type antibacterial agent as well as synthetic method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| "Improving the Antibacterial Activity of Cotton Fabrics Finished with Triclosan by the Use of 1,2,3,4-Butanetetracarboxylic Acid and Citric Acid";Mehmet Orhan et al.;《Journal of Applied polymer Science》;20081030;第1344-1352页 * |
| "三氯生接枝聚合物刷修饰的高效抗菌表面";刘传军等;《2015年全国高分子学术论文报告会》;20151021;第755页 * |
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