CN103524652A - Quaternary ammonium salt group-containing halide amine polymer antibacterial agent, and preparation method and application thereof - Google Patents
Quaternary ammonium salt group-containing halide amine polymer antibacterial agent, and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a quaternary ammonium salt group-containing halide amine polymer antibacterial agent, and a preparation method and an application thereof. The compound has a structure represented by the formula (I). The preparation method comprises the steps: with (3-acrylamidopropyl)trimethylammonium chloride as a monomer reaction raw material, sodium persulfate as an initiator and water as a solvent, carrying out a reaction, removing the solvent in the product solution, purifying, drying to obtain a precursor, then carrying out halogenation, filtration and drying to obtain the antibacterial agent finished product. The application in textile antibacterial finishing comprises placing a textile in deionized water for soaking, then placing in an antibacterial agent precursor solution, next soaking in an polymerization anionic solution having the same concentration, washing, drying, and thus completing one time assembly; repeating the above methods, totally assembling for 5-20 times, and halogenating to obtain an antibacterial fabric. The antibacterial agent has excellent antimicrobial performance, has no release of formaldehyde, and is safe and non-toxic; when the antibacterial agent is applied in the textile antibacterial finishing, the prepared antibacterial cotton fabric has good antibacterial property and high antibacterial efficiency.
Description
Technical field
The invention belongs to halogen amine antimicrobial agent synthesis technical field, be specifically related to a kind of halogen amine polymer antiseptic-germicide, preparation method and application on antibacterial textile top finish thereof containing quaternary ammonium salt group.
Background technology
In environment for human survival, exist and cause in a large number mould microorganism, and the yarn fabric such as cotton, numb can grow and breeding provides nutritive substance for these harmful microbes, therefore, textile materials is entered to antibacterial finish, make it there is good bacteriostasis antibiosis function and seem particularly important.
Common antibacterial fabric agent at present mainly comprises inorganic antiseptic, organic antibacterial agent, natural antibacterial agent and high score subclass antiseptic-germicide etc., but there is certain shortcoming in these antiseptic-germicide bacterium, such as a little less than antibacterial ability, sterilization speed is slow, price is more expensive, can produce harmful toxic byproduct etc.Recent two decades comes, the Worley professor of U.S. Auburn University and Gang professor Sun of University of California develop the novel halogen amine antimicrobial agent of a class, have sterilization speed fast, and anti-microbial property is lasting, renewable, human body and environment, without advantages such as negative impacts, and were being developed rapidly in recent years.
Yet also there are in actual applications some problems in above-mentioned halogen amine antimicrobial agent: synthesis material is expensive; Synthesis reaction temperature is high, and condition is comparatively harsh; In the middle of partial synthesis/and end product poorly water-soluble, in use procedure, need to add organic solvent hydrotropy, limited industrial application; Part chloramines class antiseptic-germicide be take N-methylol as active group, in use still has formaldehyde release And Spread of Solute.Consider the problem that the at present existing various halogen amine antimicrobial agent for antibacterial finish exist, develop the novel halogen amine antimicrobial agent that a over-all properties is superior and be extremely necessary.
Summary of the invention
For existing halogen amine antimicrobial agent, there is each side shortcoming, one of object of the present invention is to provide a kind of anti-microbial property superior, formaldehydeless release, the halogen amine polymer antiseptic-germicide containing quaternary ammonium salt group of safety non-toxic, this antiseptic-germicide is the compound of structure shown in formula (I):
In formula, R
1, R
2and R
3respectively independently selected from C
1～C
20alkyl;
X
1be selected from chlorine or bromine;
N is the polymerization degree.
Another object of the present invention is to provide a kind of preparation method of above-mentioned halogen amine polymer antiseptic-germicide, the 3-acrylamido oxypropyl trimethyl ammonium chloride of take is monomer reaction raw material, take Sodium Persulfate as initiator, take water as solvent, pass into nitrogen, at 60～80 ℃, carry out free radical reaction 8～12h; Reaction finishes, and the solvent in product solution is removed in underpressure distillation, purifies, is dried, and obtains halogen amine polymer antiseptic-germicide presoma; This presoma is dissolved in clorox, Losantin or sodium hypobromite solution, in room temperature reaction 1h, filters, dry, obtain halogen amine polymer antiseptic-germicide finished product.
Its further technical scheme is:
The mol ratio of described 3-acrylamido oxypropyl trimethyl ammonium chloride and Sodium Persulfate is 100:1.
Described halogen amine antimicrobial agent presoma is the compound of structure shown in formula (II):
In formula, n is the polymerization degree.
The mass percentage concentration of described clorox, Losantin or sodium hypobromite solution is 1～5%.
An object more of the present invention is to provide the application of above-mentioned halogen amine polymer antiseptic-germicide in textiles antibacterial finishing, pending textiles is placed in after deionized water soaks 1～3h and is taken out, the halogen amine polymer antiseptic-germicide precursor solution that is placed in concentration again and is 50～100mg/mL soaks 10～30min, after taking out, use deionized water wash, dry, then be soaked in 10～30min in the polymerization anion solutions of same concentration, after taking out, use deionized water wash, after oven dry, complete 1 assembling, repeat aforesaid method, assemble altogether 5～20 times, being selected from of described polymerization anion solutions gathers 2-acrylamide-2-methyl propane sulfonic or sodium polystyrene sulfonate, finally by halogenating reaction, make antibiotic fabric.
The consumption of described halogen amine polymer antiseptic-germicide presoma is 50～200% of described pending textiles weight, is preferably 100～160%.
Described halogenating reaction reaction solution be the solution that contains reactive halogen, comprise clorox, Losantin or sodium hypobromite solution, its mass percentage concentration is 1～10%.
Described poly-2-acrylamide-2-methyl propane sulfonic synthetic method is as follows: take 2-acrylamide-2-methyl propane sulfonic as monomer reaction raw material, take Sodium Persulfate as initiator, take water as solvent, pass into nitrogen, at 60～80 ℃, carry out free radical reaction 5～12h, reaction finishes, and solvent, the purification, dry in product solution removed in underpressure distillation, obtain, the mol ratio of described 2-acrylamide-2-methyl propane sulfonic and initiator Sodium Persulfate is 100:1.
Halogen amine polymer antiseptic-germicide of the present invention also can be used for the antibacterial finish of the materials such as synthon, gac, coating, rubber, silica gel, metal oxide or diatomite.
The present invention has following useful technique effect:
The present invention selects the alkenes compounds that contains quaternary ammonium salt group---and 3-acrylamido oxypropyl trimethyl ammonium chloride is raw material, the Sodium Persulfate of take carries out radical polymerization as initiator, prepare the poly-3-acrylamido oxypropyl trimethyl ammonium chloride of halogen amine antimicrobial agent presoma with certain polymerization degree, react with clorox/Losantin/sodium hypobromite again and generate the poly-3-acryloyl chloro oxypropyl trimethyl ammonium chloride of halogen amine polymer antiseptic-germicide, each repeating unit of this antiseptic-germicide contains a quaternary ammonium group and an antibiotic functional group, can be assembled to and contain on electronegative fabric by static assembling mode, therefore give fabric superior anti-microbial property.
Compare with existing halogen amine antimicrobial agent and preparation technology, tool of the present invention has the following advantages:
1. select synthesis material cheap and easy to get, production cost is low;
2. synthetic reaction condition is gentle, and the reaction times is short, and technological operation is simple;
3. antiseptic-germicide and presoma thereof formaldehydeless release in synthetic and use procedure, safety non-toxic, to human body and environmentally friendly;
Intermediate product presoma and end product antiseptic-germicide all have well water-soluble, in use procedure without adding organic solvent hydrotropy, safe ready;
5. by antiseptic-germicide of the present invention, carry out the textiles that antibacterial finish makes and there is excellent anti-microbial property, sterilization speed is fast, antimicrobial efficiency is high, its active chlorine content can reach 0.40%, antibiotic rate to streptococcus aureus in 30min reaches 100%, in 30min to Escherichia coli O 157: the antibiotic rate of H7 reaches 99.73%.
Accompanying drawing explanation
Fig. 1 is the synthetic route chart of halogen amine polymer antiseptic-germicide presoma and halogen amine polymer antiseptic-germicide in the embodiment of the present invention 1.
Fig. 2 is the antiseptic-germicide sterilization of halogen amine polymer and anti-microbial property regeneration principle schematic diagram in the embodiment of the present invention 1.
Embodiment
Below in conjunction with accompanying drawing, and by embodiment, the present invention is specifically described.
As shown in Figure 1, monomer 3-acrylamido oxypropyl trimethyl ammonium chloride produces free radical under Sodium Persulfate causes, and further chainpropagation, generation has the poly-3-acrylamido oxypropyl trimethyl ammonium chloride of halogen amine polymer antiseptic-germicide presoma of certain polymerization degree (polymerization degree is random), finally by chlorination reaction, on this presoma, introduce oxidisability chlorine atom, generate the poly-3-acryloyl chloro oxypropyl trimethyl ammonium chloride of halogen amine polymer antiseptic-germicide with anti-microbial property.
As shown in Figure 2, on the one hand, the halogen amine polymer antiseptic-germicide on textile fiber is by chlorine atom performance antibiotic effect, and on the other hand, due to sterilization, used up chlorine atom can be supplemented and be regenerated by the solution containing reactive chlorine.
Halogen amine polymer antiseptic-germicide and precursor synthesis embodiment thereof
Embodiment 1
Take the 3-acrylamido oxypropyl trimethyl ammonium chloride of 27.56g70～80% in there-necked flask, add 150mL water, then add 0.12g Sodium Persulfate, pass into after nitrogen 30min, be warming up to 80 ℃, reaction 8h; After reaction finishes, by underpressure distillation, remove the water in product solution, by gained solute ethanol purification, by the product obtaining at 60 ℃, under the condition of 0.2MPa, be placed in the dry 12h of vacuum drying oven, obtain the poly-3-acrylamido oxypropyl trimethyl ammonium chloride of halogen amine compound presoma; It is in 1% chlorine bleach liquor that this presoma is dissolved in to mass percentage concentration, in room temperature standing and reacting 1h, reaction finishes, and according to routine operation method, filters, is dried, and obtains the poly-3-acryloyl chloro oxypropyl trimethyl ammonium chloride of halogen amine polymer antiseptic-germicide finished product.
Embodiment 2
Take the 3-acrylamido oxypropyl trimethyl ammonium chloride of 27.56g70～80% in there-necked flask, add 150mL water, then add 0.12g Sodium Persulfate, pass into after nitrogen 30min, be warming up to 60 ℃, reaction 12h; After reaction finishes, by underpressure distillation, remove the water in product solution, by gained solute ethanol purification, by the product obtaining at 60 ℃, under the condition of 0.2MPa, be placed in the dry 12h of vacuum drying oven, obtain the poly-3-acrylamido oxypropyl trimethyl ammonium chloride of halogen amine compound presoma; It is in 5% chlorine bleach liquor that this presoma is dissolved in to mass percentage concentration, in room temperature standing and reacting 1h, reaction finishes, and according to routine operation method, filters, is dried, and obtains halogen amine polymer antiseptic-germicide finished product 3-acryloyl chloro oxypropyl trimethyl ammonium chloride.
Halogen amine polymer antiseptic-germicide Application Example
Application Example 1
Take the poly-3-acrylamido oxypropyl trimethyl ammonium chloride of obtained halogen amine polymer antiseptic-germicide presoma in 8.0g embodiment 1 and be dissolved in 100mL water, stir it is dissolved completely, be configured to positively charged ion halogen amine dressing liquid; The poly-2-acrylamide-2-methyl propane sulfonic of 8.0g is dissolved in 100mL water, the NaOH solution with 10% adjusts pH to neutral, stirs, and is prepared into negatively charged ion halogen amine dressing liquid again; The pending cotton fabric of 5g (purchased from Zhejiang Guandong Dyeing and Garment Co., Ltd.) is placed in after deionized water soaks 1h and is taken out, then be placed in positively charged ion halogen amine dressing liquid and soak 10min, after taking-up, in deionized water, wash 5min, dry; Then cotton fabric is placed in to negatively charged ion halogen amine dressing liquid, dipping 10min washs 5min in deionized water after taking-up, complete 1 assembling after oven dry, repeats aforesaid method, assembles 5 times; It is in 1% chlorine bleach liquor that cotton fabric after drying is soaked in to mass percentage concentration, takes out this cotton fabric after 1h, dries 2h in 45 ℃ in dryer, makes antibiotic cotton fabric.By the active chlorine content of this antibiotic cotton fabric of iodometric determination, its chlorinity is 0.35%.
Above-mentioned poly-2-acrylamide-2-methyl propane sulfonic preparation method is as follows: take 2-acrylamide-2-methyl propane sulfonic as monomer reaction raw material, take Sodium Persulfate as initiator, take water as solvent, pass into nitrogen, at 60 ℃, carry out free radical reaction 12h, reaction finishes, and solvent, the purification, dry in product solution removed in underpressure distillation, obtain, the mol ratio of described 2-acrylamide-2-methyl propane sulfonic and initiator Sodium Persulfate is 100:1.
Application Example 2
Take the poly-3-acrylamido oxypropyl trimethyl ammonium chloride of obtained halogen amine antimicrobial agent presoma in 8.0g embodiment 2 and, in 100mL water, stir it is dissolved completely, be configured to positively charged ion halogen amine dressing liquid; Again 8.0g sodium polystyrene sulfonate is dissolved in 100mL water, stirs, be prepared into negatively charged ion dressing liquid; After the pending cotton fabric of 8.0g (the same) is soaked to 3h in deionized water, take out, then be placed in positively charged ion halogen amine dressing liquid and soak 30min, after taking-up, in deionized water, wash 5min, dry; Then cotton fabric is placed in to negatively charged ion dressing liquid and soaks 30min, after taking-up, in deionized water, wash 5min, after oven dry, complete 1 antiseptic-germicide assembling, repeat aforesaid method, assemble 5 times; It is in 10% calcium hypochlorite solution that cotton fabric after drying is soaked in to mass percentage concentration, takes out this cotton fabric after 1h, dries 2h in 45 ℃ in dryer, makes antibiotic cotton fabric.By the active chlorine content of this antibiotic cotton fabric of iodometric determination, its chlorinity is 0.40%.
Testing of Antibacterial Property on Textile
According to method described in correction AATCC100-1999 anti-microbial property testing standard, test.
Get in Application Example 1 three parts of identical cotton fabrics, first part be left intact (blank cotton); Second part is carried out antibacterial finish (specimen) according to method described in Application Example 1, and the 3rd part for the treatment of process be with second part, but does not carry out chloridized (blank sample); Inoculated bacteria is streptococcus aureus and Escherichia coli O 157: H7, and test result is respectively referring to table 1 and table 2.
The anti-microbial property of table 1 antibacterial fabric to streptococcus aureus
Note: the inoculum density of streptococcus aureus: 1.00 * 10
6cfu.
The anti-microbial property of table 2 antibacterial fabric to Escherichia coli O 157: H7
Note: the inoculum density of Escherichia coli O 157: H7: 2.70 * 10
6cfu.
The test data of table 1 and table 2 shows, antiseptic-germicide of the present invention is applied to textiles antibacterial finishing, and obtained antibiotic cotton fabric has good antimicrobial property, and antimicrobial efficiency is high; After contacting with inoculated bacteria, the antibiotic rate to streptococcus aureus in 30min reaches 100%, in 30min to Escherichia coli O 157: the antibiotic rate of H7 reaches 99.73%.
The related raw material of above embodiment and Application Example and reagent are commercially available prod, and institute's use production unit is this area conventional equipment, and wherein, streptococcus aureus and Escherichia coli O 157: H7 is purchased from US mode culture collection warehousing (ATCC).
The above be only the preferred embodiment of the present invention, the invention is not restricted to above embodiment.Be appreciated that the oher improvements and changes that those skilled in the art directly derive or associate without departing from the spirit and concept in the present invention, within all should thinking and being included in protection scope of the present invention.
Claims (10)
1. containing a halogen amine polymer antiseptic-germicide for quaternary ammonium salt group, it is characterized in that the compound for structure shown in formula (I):
In formula, R
1, R
2and R
3respectively independently selected from C
1～C
20alkyl;
X
1be selected from chlorine or bromine;
N is the polymerization degree.
2. described in claim 1, contain the preparation method of the halogen amine polymer antiseptic-germicide of quaternary ammonium salt group, it is characterized in that: the 3-acrylamido oxypropyl trimethyl ammonium chloride of take is monomer reaction raw material, take Sodium Persulfate as initiator, take water as solvent, pass into nitrogen, at 60～80 ℃, carry out free radical reaction 8～12h; Reaction finishes, and the solvent in product solution is removed in underpressure distillation, purifies, is dried, and obtains halogen amine polymer antiseptic-germicide presoma; This presoma is dissolved in clorox, Losantin or sodium hypobromite solution, in room temperature reaction 1h, filters, dry, obtain halogen amine polymer antiseptic-germicide finished product.
3. contain as claimed in claim 2 the preparation method of the halogen amine polymer antiseptic-germicide of quaternary ammonium salt group, it is characterized in that: the mol ratio of described 3-acrylamido oxypropyl trimethyl ammonium chloride and Sodium Persulfate is 100:1.
4. contain as claimed in claim 2 the preparation method of the halogen amine polymer antiseptic-germicide of quaternary ammonium salt group, it is characterized in that: described halogen amine antimicrobial agent presoma is the compound of structure shown in formula (II):
In formula, n is the polymerization degree.
5. contain as claimed in claim 2 the preparation method of the halogen amine polymer antiseptic-germicide of quaternary ammonium salt group, it is characterized in that: the mass percentage concentration of described clorox, Losantin or sodium hypobromite solution is 1～5%.
6. the application in textiles antibacterial finishing containing the halogen amine polymer antiseptic-germicide of quaternary ammonium salt group described in claim 1, it is characterized in that: pending textiles is placed in after deionized water soaks 1～3h and is taken out, the halogen amine polymer antiseptic-germicide precursor solution that is placed in concentration again and is 50～100mg/mL soaks 10～30min, after taking out, use deionized water wash, dry, then be soaked in 10～30min in the polymerization anion solutions of same concentration, after taking out, use deionized water wash, after oven dry, complete 1 assembling, repeat aforesaid method, assemble altogether 5～20 times, being selected from of described polymerization anion solutions gathers 2-acrylamide-2-methyl propane sulfonic or sodium polystyrene sulfonate, finally by halogenating reaction, make antibiotic fabric.
7. the application in textiles antibacterial finishing containing the halogen amine polymer antiseptic-germicide of quaternary ammonium salt group as claimed in claim 6, is characterized in that: the consumption of described halogen amine polymer antiseptic-germicide presoma is 50～200% of described pending textiles weight.
8. the application in textiles antibacterial finishing containing the halogen amine polymer antiseptic-germicide of quaternary ammonium salt group as claimed in claim 6, it is characterized in that: described halogenating reaction reaction solution be the solution that contains reactive halogen, comprise clorox, Losantin or sodium hypobromite solution, its mass percentage concentration is 1～10%.
9. the application in textiles antibacterial finishing containing the halogen amine polymer antiseptic-germicide of quaternary ammonium salt group as claimed in claim 6, it is characterized in that described poly-2-acrylamide-2-methyl propane sulfonic synthetic method is as follows: take 2-acrylamide-2-methyl propane sulfonic as monomer reaction raw material, take Sodium Persulfate as initiator, take water as solvent, pass into nitrogen, at 60～80 ℃, carry out free radical reaction 5～12h, reaction finishes, the solvent in product solution is removed in underpressure distillation, purify, dry, obtain, the mol ratio of described 2-acrylamide-2-methyl propane sulfonic and initiator Sodium Persulfate is 100:1.
10. the application in textiles antibacterial finishing containing the halogen amine polymer antiseptic-germicide of quaternary ammonium salt group as claimed in claim 7, is characterized in that: the consumption of described halogen amine polymer antiseptic-germicide presoma is 100～160% of described pending textiles weight.
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|---|---|---|---|---|
| CN103757906A (en) * | 2014-02-18 | 2014-04-30 | 江南大学 | Preparation method of olefine halamine compound grafted antibacterial cotton fabric containing quaternary ammonium groups |
| CN104358104A (en) * | 2014-11-07 | 2015-02-18 | 江南大学 | Method for preparing antimicrobial textiles by using electronic radiation technology |
| CN104497184A (en) * | 2014-12-15 | 2015-04-08 | 中国科学院合肥物质科学研究院 | Preparation method of high-relative-molecular-mass acrylamidipropyl trimethyl ammonium cationic monomer homopolymer |
| CN105237668A (en) * | 2014-08-28 | 2016-01-13 | 江苏神涛环保科技有限公司 | Preparation method and application of novel high-molecular quaternary ammonium salt antibacterial finishing agent |
| CN105601778A (en) * | 2016-01-19 | 2016-05-25 | 江南大学 | Annular halamine type polymeric antibacterial agent containing quaternary ammonium group and preparation method and application of polymeric antibacterial agent |
| CN107313252A (en) * | 2017-07-28 | 2017-11-03 | 苏州井村服饰有限公司 | A kind of cowboy's antibacterial stiffening agent and preparation method thereof |
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| CN113444197A (en) * | 2020-03-24 | 2021-09-28 | 合肥杰事杰新材料股份有限公司 | Halamine antibacterial agent and preparation method and application thereof |
| CN113638226A (en) * | 2021-09-17 | 2021-11-12 | 四川华纺银华有限责任公司 | Finishing method of antibacterial fiber, fiber and textile fabric |
| CN115142299A (en) * | 2022-07-15 | 2022-10-04 | 安徽紫江喷铝环保材料有限公司 | Plastic-free coating environment-friendly packaging material |
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| CN105237668A (en) * | 2014-08-28 | 2016-01-13 | 江苏神涛环保科技有限公司 | Preparation method and application of novel high-molecular quaternary ammonium salt antibacterial finishing agent |
| CN104358104A (en) * | 2014-11-07 | 2015-02-18 | 江南大学 | Method for preparing antimicrobial textiles by using electronic radiation technology |
| CN104358104B (en) * | 2014-11-07 | 2016-06-15 | 江南大学 | A kind of method utilizing electron radiation technology to prepare antibacterial fabric |
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| CN115142299A (en) * | 2022-07-15 | 2022-10-04 | 安徽紫江喷铝环保材料有限公司 | Plastic-free coating environment-friendly packaging material |
| CN118480147A (en) * | 2024-07-16 | 2024-08-13 | 内蒙古大学 | Preparation method and application of N-halamine antibacterial agent modified water absorption pad |
| CN118480147B (en) * | 2024-07-16 | 2024-09-24 | 内蒙古大学 | Preparation method and application of N-halamine antibacterial agent modified water absorption pad |
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