CN101798324B - Method for preparing antibacterial agent achieving antibacterial effect on decorative textile fabric - Google Patents
Method for preparing antibacterial agent achieving antibacterial effect on decorative textile fabric Download PDFInfo
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- CN101798324B CN101798324B CN201010123674.2A CN201010123674A CN101798324B CN 101798324 B CN101798324 B CN 101798324B CN 201010123674 A CN201010123674 A CN 201010123674A CN 101798324 B CN101798324 B CN 101798324B
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Abstract
The invention relates to a method for preparing antibacterial agent achieving the antibacterial effect on textile finishing fabric. The method comprises the following steps: mixing silane and tertiary amine by the ratio of 1:1.5-3 in a 100mL 4-neck flask equipped with a thermometer, a reflux condensation tube and a stirrer; adding 0.15%-3% sodium iodide as a catalyst and 1.2%-2.5% antioxidant as well as organic solvent at the same time to the mixture; feeding in protective nitrogen; controlling the temperature of the reaction system within 65 to 80 DEG C; stirring and reacting; and cooling and discharging after the reaction to obtain the light yellow liquid antibacterial finishing agent, wherein the reaction equation is shown as below.
Description
Technical field
The present invention relates to a kind of a kind of preparation method for antibacterial agent achieving antibacterial effect on decorative textile fabric with antibacterial, belong to textile decoration fabric and manufacture field.
Background technology
CNCN1568704A, title " a kind of combined nano anti-biotic material and preparation method thereof and product ", 1. for the deficiency of single nano anti-biotic material, adopted nanometer combination antimicrobial technology that the anti-biotic material of different anti-microbial effects is combined and prepares combined nano anti-biotic material, utilize the collaborative and coupling between nanoparticle, greatly improved antibacterial ability; 2. with the anti-biotic material of the method development, have broad-spectrum antimicrobial function, it has good kill activity to multiple germs (poison) such as streptococcus aureus, pathogenic colon bacillus, gonococcus, syphilis fungus; 3. the method can be for making the various anti-biotic materials that bacterium and virus are had to kill activity as antibiotic facing material, antibiotic plastic, antibacterial latex product etc.Its weak point: be not suitable for the aftertreatment of textile decoration fabric.
CN101363141A, title " full light extinction and its preparation method and application ", 0.5～3 part of modification antiseptic-germicide, 99.5～97 parts of full-dull terylene thread-forming polyesters.Can be applicable to the field of taking, decoration field and industrial field, prepare all kinds of antibacterial decoration body of wall fabrics, antibacterial working suit, antibiotic facing material.Full light extinction of the present invention, antiseptic-germicide addition is few, excellent property, antiseptic-germicide and full-dull agent synergy, spinning properties is improved, good anti-bacterial effect,, the original performance and the production requirement that substantially do not affect material good with macromolecular material consistency.Adopt full-dull polyester and antibacterial matrices co-blended spinning production technique easily to realize, be convenient to improve antibacterial fiber spinning effect and give fiber full-dull characteristic simultaneously.The antibacterial dacron long filament performance index conformance with standard requirement that present method is manufactured, fiber softening high resilience, anti-microbial property is good, and the antibacterial effect phase is long.Its weak point: adopt the germ resistance of fabric itself to reach antibacterial to fabric harmful microbe, but in actual woven process, because the yarn of weaving spins, dyes at machine in the process of system, rear arrangement, of its fabric itself, with harmful microorganism, therefore cannot reach antibacterial effect at all.
Summary of the invention
Purpose of design: avoid the weak point in background technology, design textile decoration fabric after a kind of aftertreatment and have a kind of preparation method for antibacterial agent achieving antibacterial effect on decorative textile fabric of good antibacterial effect.
Design: on textiles, harmful microbe growth and breeding has brought many health threat to the mankind, carries out hygienic finishing to textiles and can make fabric have anti-microbial effect, resists the infringement of all kinds of germs to the mankind.In the eurypalynous textile antimicrobial agent of crowd, organosilicon quaternary ammonium salt is the comparatively ideal antiseptic-germicide of a class over-all properties.With low-cost industrial, produce such antiseptic-germicide, have certain realistic meaning.The present invention is take γ-r-chloropropyl trimethoxyl silane and tertiary amine as raw material, and sodium iodide is catalyzer, adopts directly synthetic γ-r-chloropropyl trimethoxyl silane quaternary ammonium salt of single step reaction.
Technical scheme 1: a kind of preparation method for antibacterial agent achieving antibacterial effect on decorative textile fabric; in the 100mL four-hole boiling flask that thermometer, reflux condensing tube and agitator are housed, after 1: 1.5～3 silane, tertiary amine are mixed, add 0.15%～3% catalyzer iodate sodium and 1.2%～2.5% oxidation inhibitor; add organic solvent simultaneously; logical nitrogen protection, 65～80 ℃ of the hierarchies of control, stirring reaction; after reaction finishes; cooling discharging, obtains weak yellow liquid antibacterial finishing agent, and its reaction equation is as follows:
Technical scheme 2: a kind of antibacterial textile decoration fabric, it comprises fabric, it is characterized in that: technique is padded in employing and impregnation technology arranges fabric, concrete finishing technique is as follows:
Pad technique: antibacterial finishing agent 40g/L, fabric two is soaked to two and roll (pick-up 70%), 160 ℃ of baking temperatures, bake time 60s;
Impregnation technology: antibacterial finishing agent 40g/L, caustic soda 4g/L, bath raio 1: 30, finish fabric 30min at 95 ℃.
The present invention compared with background technology, the one, all raw material of the present invention and condition meet industrial production condition, efficiency is high; The 2nd, the present invention is take methyl alcohol, methyl-sulphoxide as raw material mixing, and the relative consumption of sodium iodide is back flow reaction 48h under 0.05,65 ℃ of condition, and productive rate is 82.39%; The 3rd, this organosilicon antibacterial agent belongs to nanometer materials, its strong adhesion; The 3rd, the present invention can be with padding, impregnation technology arranges and realizes its function, is conducive to realize its technique; The 4th, germ resistance, the washing fastness of non-woven fabrics, pure cotton knitted fabric and pure polyester knitting thing after the present invention arranges, than at present good in the product effect of use; The 5th, in fabric molecular structure, there is hydroxyl, be conducive to chemical in conjunction with antiseptic-germicide, improve antibacterial washing fastness.
Accompanying drawing explanation
Fig. 1 is the affect schematic diagram of solvent load on product yield.
Fig. 2 is the schematic diagram of the impact of reaction times on productive rate.
Fig. 3 is product infrared spectrogram.
Fig. 4 is product nmr spectrum.
Fig. 5 is the affect schematic diagram of antimicrobial fluid concentration on bacteriostasis rate.
Embodiment
Embodiment 1: a kind of preparation method for antibacterial agent achieving antibacterial effect on decorative textile fabric; in the 100mL four-hole boiling flask that thermometer, reflux condensing tube and agitator are housed, after 1: 1.5～3 silane, tertiary amine are mixed, add 0.15%～3% catalyzer iodate sodium and 1.2%～2.5% oxidation inhibitor; add organic solvent simultaneously; logical nitrogen protection, 65～80 ℃ of the hierarchies of control, stirring reaction; after reaction finishes; cooling discharging, obtains weak yellow liquid antibacterial finishing agent, and its reaction equation is as follows:
Described organic solvent with methyl alcohol, methyl-sulphoxide in 4～2.5: 1 ratio is mixed, and consumption is 30～40%, 65～80 ℃ of temperature of reaction, the reaction yield after reaction 48h can reach more than 80%.
Embodiment 2: on the basis of embodiment 1, after the silane of 1: 1.5, tertiary amine are mixed, add 0.15% catalyzer iodate sodium and 1.2% oxidation inhibitor.
Embodiment 3: on the basis of embodiment 1, after the silane of 1: 3, tertiary amine are mixed, add 3% catalyzer iodate sodium and 2.5% oxidation inhibitor.
Embodiment 4: on the basis of embodiment 1, after the silane of 1: 2, tertiary amine are mixed, add 1% catalyzer iodate sodium and 1.5% oxidation inhibitor.
Embodiment 5: on the basis of embodiment 1, after the silane of 1: 2.5, tertiary amine are mixed, add 1.5% catalyzer iodate sodium and 2% oxidation inhibitor.
Embodiment 6: on the basis of embodiment 1, after the silane of 1: 1.8, tertiary amine are mixed, add 2% catalyzer iodate sodium and 1.8% oxidation inhibitor.
Embodiment 7: on the basis of embodiment 1～6, a kind of antibacterial textile decoration fabric, it comprises fabric, and technique is padded in employing and impregnation technology arranges fabric, and concrete finishing technique is as follows:
Pad technique: antibacterial finishing agent 40g/L, fabric two is soaked to two and roll (pick-up 70%), 160 ℃ of baking temperatures, bake time 60s;
Impregnation technology: antibacterial finishing agent 40g/L, caustic soda 4g/L, bath raio 1: 30, finish fabric 30min at 95 ℃.
1.1 main medicine and instruments
Fabric: non-woven fabrics, pure cotton knitted fabric, pure polyester knitting thing, Curtains Fabrics (Hangzhou Hightex Co., Ltd. provides).
Medicine: anhydrous methanol, dehydrated alcohol, sodium iodide, sodium-chlor, Silver Nitrate, potassium bichromate, sodium hydroxide, Sodium phosphate dibasic, potassium primary phosphate, is analytical reagent; Beef Tianjin cream, peptone, agar, is biochemical reagents, γ-r-chloropropyl trimethoxyl silane, Dodecyl Dimethyl Amine, washing composition (self-control).
Test organisms: colibacillus, streptococcus aureus, Candida albicans (providing by Changzhou First People's Hospital).
Instrument: W2-180SP thermostat water bath, Athletic1098XS automatic rotary drum washing machine, SW-24A colour fastness to washing trier, powerful colorable resin machine, SN-CJ-2FD clean bench, the HZQ-C airbath vibrator of pressing of PBO, GNP-9160 water isolation type constant incubator, DHG-9123A electric heating constant-temperature blowing drying box, R-6 automatic sizing dryer, Nicolet
460 type Fourier infrared spectrographs, AVANCE III 500MHz nucleus magnetic resonance.
1.2 γ-r-chloropropyl trimethoxyl silane quaternary ammonium salt is synthetic
In the 100mL four-hole boiling flask that thermometer, reflux condensing tube and agitator are housed; silane, tertiary amine and catalyzer iodate sodium are added according to a certain ratio, add appropriate organic solvent and a small amount of oxidation inhibitor, logical nitrogen protection simultaneously; hierarchy of control certain temperature, stirring reaction.After reaction finishes, cooling discharging, obtains weak yellow liquid product.
Reaction equation is as follows:
1.3 productive rates are measured
By tetrabromophenol sulfonphthalein, make two-phase indicator, ethylene dichloride is made a point phase solvent, with cats product solution titration sodium laurylsulfonate standardized solution to be measured, aobvious blue to lower floor's solvent layer, can direct quantitative cats product
[1].
1.4 structural characterization
To synthetic product underpressure distillation except desolventizing, and with washing with acetone for several times, recrystallization carries out Fourier's infrared spectra (FT-IR) and is that solvent carries out nucleus magnetic resonance test with heavy water with KBr smear after purifying.
1.5 finishing technique
Technique is padded in employing and impregnation technology arranges fabric, and concrete finishing technique is as follows:
Pad technique: antibacterial finishing agent 40g/L, two soak two rolls (pick-up 70%), and 160 ℃ of baking temperatures, bake time 60s;
Impregnation technology: antibacterial finishing agent 40g/L, caustic soda 4g/L, bath raio 1: 30, arranges 30min at 95 ℃.1.7 product
Anti-microbial property is measured
Adopt succusion
[2]antibacterial finish fabric is carried out to the quantitative assay of antibacterial effect.Choose 0.75g antibiotic fabric, be dipped in the buffered soln that contains specified germ concentration, be placed in shaking culture case shaking culture 18h, by measuring the breeding situation of bacterium in solution, obtain the antibacterial effect of fabric.
1.6 washing fastness tests
With reference to FZ/T 73023, carry out washing fastness invention.By the cloth specimen arranging according to washing composition 2g/L, bath raio 1: 30, the washing of condition that water temperature is 40 ℃.Every washing 5min post rinsing twice, this is once effectively washing.Washing several times, can carry out antibacterial test to cloth specimen after drying.
Result and discussion
The selection of 1.1 reaction conditionss
Tertiary amine belongs to typical S with reacting of γ-chloropropyl silane
n2 bimolecular nucleophilic substitution courses
[3], sterically hindered larger between group, the relative difficulty of carbon atom contact of attack reagent tertiary amine and C-X key band portion positive center, speed of reaction is lower.The factors such as solvent property, temperature of reaction, reaction times all can exert an influence to the carrying out of reaction.
1.1.1 the impact of different solvents and temperature of reaction
The polar solvent that specific inductivity is large is conducive to dissociating of alkyl halide, accelerates reaction process, uses methyl alcohol as solvent synthesizing organo-silicon quaternary ammonium salt antiseptic in United States Patent (USP).Ethanol relative cost is low, safe, selects ethanol to contrast invention as solvent, has attempted making solvent with mixed solution simultaneously, and result is as shown in table 1.
The impact on product yield of table 1 solvent and temperature of reaction
Note: the relative mole dosage of sodium iodide is 0.05, churning time is 48h;
Relative mole dosage=the sodium iodide of sodium iodide mole dosage number: tertiary amine mole dosage number.
Table 1 data presentation, take methyl alcohol as solvent, product yield is 65.49%, and using methyl alcohol, methyl-sulphoxide as mixed solvent, product yield can reach 82.39%.Different solvents has a certain impact to reaction, and aprotic, polar type solvent is conducive to the generation of quaterisation, the adding of methyl-sulphoxide in methyl alcohol, has further reduced the activation energy of reaction, has promoted quaterisation.Make solvent with ethanol, product yield is 79.43%.Ethanol polarity is slightly little, but system temperature can rise to 80 ℃, and temperature height is more conducive to the carrying out of reaction.
1.1.2 the impact of solvent load on product yield
Solvent add membership diluting reaction thing, product yield is produced to certain influence.Change the amount of methyl alcohol, methyl-sulphoxide mixed solvent, check the impact of solvent load on product yield, result as shown in Figure 1.Note: the relative mole dosage of sodium iodide is 0.05, temperature of reaction is 65 ℃, churning time is 48h.
As shown in Figure 1, methyl alcohol methyl-sulphoxide mixed solvent consumption is larger on product yield impact, and when mixed solvent consumption is 30%, it is maximum that product yield reaches.Polar solvent can increase the nucleophilic activity of tertiary amine
[3], being conducive to reaction and carrying out towards positive reaction direction, solvent load is too low, can reduce speed of reaction.Solvent is too much, can greatly reduce reactant concn, also can reduce effecting reaction speed.
1.1.3 the impact of catalyst levels
The C-X bond rupture of chloropropyl silane is more difficult, improves the polarization of C-X key, contributes to leaving away of halogen on C-X key
[3].Utilize iodide and the replaceable feature of C-C1 key, add appropriate iodide to make catalyzer, can effectively promote the carrying out of reaction.Change sodium iodide consumption, investigate the impact of catalyst levels on productive rate, result is as table 2.
The impact of table 2 sodium iodide consumption on productive rate
Note: methyl alcohol, methyl-sulphoxide are made mixed solvent, temperature of reaction is 65 ℃, churning time is 48h.
Shown in table 2 data, when the relative consumption of sodium iodide is 0.10, the transformation efficiency of product reaches 84.28%, and so, than 0.05 consumption, productive rate amplification is little.From production cost, consider, select 0.05 consumption to be advisable.
1.1.4 the impact of reaction times on product yield
This quaterisation can be more consuming time
[3], the reaction times is started to change from 24h, watch the impact of reaction times on product yield, the results are shown in Figure 2.Note: methyl alcohol, methyl-sulphoxide are made mixed solvent, the relative mole dosage of sodium iodide is 0.05, temperature of reaction is 65 ℃.
By Fig. 2, can clearly be found out, from 24h, start near 42h, the increasing degree of productive rate is larger.Stir that 48h is follow-up renews the long reaction times, productive rate is substantially constant.
1.1.5 product structure characterizes
Product structure is characterized with Fourier's infrared spectra, the results are shown in Figure 3.Product is characterized with nucleus magnetic resonance, the results are shown in Figure 4.
Ownership (the v/cm of each absorption peak in infrared spectrum
-1) as follows: 2923.88,2852.52 (s, v C-H ,-CH
2); 1467.73,1377.08 (s, δ C-H ,-CH
3,-CH
2); 1197 (m, v Si-O-C, v C-O); 1095 (s, vSi-O-C, v C-O); 956.41 (m, v Si-O-C, v C-N), 721.96cm
-1for (CH in molecule
2) absorption peak of n (n>=4) methene chain.
By
1hNMR spectrogram can be found out, is silicon methoxy base peak near δ=2.78, being n-formyl sarcolysine base peak on organosilicon quaternary ammonium salt, is the nitrogen methylene peak on organosilicon quaternary ammonium salt near δ=3.22 near δ=3.05.
Comprehensive two spectrograms, can judge that this compound is as target product.
1.2 anti-microbial property test results
1.2.1 antiseptic-germicide consumption impact invention
With reference to technique shown in 1.4, adjust antiseptic-germicide concentration, arrange pure cotton woven fabric with padding method, and wash 50 times, select streptococcus aureus as bacterial classification to be measured, result is as shown in Figure 5.
As seen from Figure 5, when antiseptic-germicide concentration is too low, fungistatic effect is very poor, and the minimal inhibitory concentration of this and bacterium has relation, when the concentration of antiseptic-germicide on fabric is during higher than minimal inhibitory concentration, has fungistatic effect, if lower than minimal inhibitory concentration, without fungistatic effect.Meanwhile, antiseptic-germicide consumption exceedes 40g/L, and finish fabric keeps constant to the fungistatic effect of streptococcus aureus, and, under 40g/L concentration, fabric reaches capacity to the absorption combination of antiseptic-germicide, without the consumption that improves again antiseptic-germicide.
1.2.2 finishing technique comparison test
Impregnation technology is postfinishing process conventional in factory with padding technique, with synthesized antiseptic-germicide, pure cotton knitted fabric, pure polyester knitting thing is carried out to antibacterial finish, and test the antibacterial washing fastness of finish fabric according to processing condition shown in 1.4, and test result is in Table 3.
The different finishing technique anti-bacteria test result of table 3
Pure cotton knitted fabric and pure polyester knitting thing arrange with two kinds of different process, and after 50 washings, bacteriostasis rate is all more than 60%, and two kinds of techniques are all applicable to the arrangement of this antiseptic-germicide.
Antibacterial finish fabric also has antibacterial effect after washing for several times, it may be Trimethoxy silane base because in succession in antiseptic-germicide one end of synthesized, it has silane contingency, after meeting water, form silanol base, can with fiber on hydroxyl generation dehydration condensation, being attached on fabric of chemical, has improved the washing fastness of antibiotic fabric thus
[7].The main component of right washing composition used is anion surfactant, and it can be combined with the quaternary ammonium salt of cationic, can greatly weaken the antibacterial washing fastness of fabric, thus finish fabric through 50 times washing after, bacteriostasis rate significantly reduces.
1.1.1 different finish fabric antibacterial tests
With padding technique, arrange different size Curtains Fabrics, impregnation technology dressed nonwoven fabrics, tests its antibacterial effect, the results are shown in Table 4.
The different finish fabric anti-bacteria test result of table 4
Non-woven fabrics intensity is low, not water-fastness, therefore after antibacterial finish, only to its washing 10 times.After 10 washings, non-woven fabrics all reaches more than 90% the bacteriostasis rate of three kinds of bacteriums, and the Curtains Fabrics after antibacterial finish also still has certain anti-microbial effect after 50 washings.Associative list 3, the discovery of table 4 data, in fabric, terylene content is more, and antibacterial washing fastness is poorer.From woven fabric structure performance, may be because the essentially consist material of viscose fiber and linen-cotton is all Mierocrystalline cellulose, contain more rich hydroxyl, and on polyster fibre, hydroxyl comparatively small amt causes.
It is to be understood that: although above-described embodiment is to the mentality of designing of the present invention detailed text description of contrasting; but these text descriptions; just the simple text of mentality of designing of the present invention is described; rather than the restriction to mentality of designing of the present invention; any combination, increase or modification that does not exceed mentality of designing of the present invention, all falls within the scope of protection of the present invention.
Claims (1)
1. a preparation method for antibacterial textile decoration fabric, is characterized in that: comprise the step that antiseptic-germicide preparation process and antiseptic-germicide arrange fabric,
(1) antiseptic-germicide preparation process:
In the 100mL four-hole boiling flask that thermometer, reflux condensing tube and agitator are housed; after the silane of 1:1.5～3, tertiary amine are mixed; add 0.15%～3% catalyzer iodate sodium and 1.2%～2.5% oxidation inhibitor; add simultaneously 30～40% in the methyl alcohol of 4～2.5:1 ratio, methyl-sulphoxide mixed solvent; logical nitrogen protection; 65～80 ℃ of the reaction hierarchies of control; stirring reaction; reaction yield after reaction 48h can reach more than 80%; cooling discharging; obtain weak yellow liquid antibacterial finishing agent, its reaction equation is as follows:
(2) step that antiseptic-germicide arranges fabric: technique is padded in employing and impregnation technology arranges fabric, concrete finishing technique is as follows:
Pad technique: antibacterial finishing agent 40g/L, fabric two is soaked to two and roll, pick-up 70%, 160 ℃ of baking temperatures, bake time 60s;
Impregnation technology: antibacterial finishing agent 40g/L, caustic soda 4g/L, bath raio 1:30, finish fabric 30min at 95 ℃; Described fabric is selected from pure cotton knitted fabric and terylen knitted fabrics;
Antiseptic-germicide consumption exceedes 40g/L, finish fabric keeps constant to the fungistatic effect of streptococcus aureus, under 40g/L concentration, fabric reaches capacity to the absorption combination of antiseptic-germicide, without the consumption that improves again antiseptic-germicide, the pure cotton knitted fabric arranging through this antiseptic-germicide and pure polyester knitting thing are after 50 washings, and bacteriostasis rate is all more than 60%.
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| CN103276596B (en) * | 2013-05-29 | 2015-07-01 | 上海师范大学 | Preparation method of quaternized halamine antibacterial cotton fiber |
| CN103388217B (en) * | 2013-08-09 | 2015-11-18 | 吴江金时利织造有限公司 | A kind of Dacron jacquard fabric and production method thereof |
| CN103572594A (en) * | 2013-11-20 | 2014-02-12 | 苏州大学 | Antibacterial agent containing fluorinated alkyl quaternary ammonium salt, and preparation method and application of antibacterial agent |
| CN104031081B (en) * | 2014-03-06 | 2017-03-29 | 苏州大学 | A kind of multiamide antibacterial, preparation method and applications |
| CN104153186B (en) * | 2014-07-14 | 2016-04-20 | 桐乡大和纺织服饰有限公司 | High-efficiency antimicrobial self-cleaning finishing agent and preparation method thereof and using method |
| CN104179010A (en) * | 2014-08-11 | 2014-12-03 | 李济锋 | Preparation method of antibacterial antifouling agent for cloth |
| CN105463840A (en) * | 2015-11-18 | 2016-04-06 | 崔志锋 | A novel polymer antibacterial agent |
| CN107217480B (en) * | 2017-06-22 | 2018-10-02 | 盐城工学院 | Finishing agent with antibacterial and flame retardant property and its preparation method and application method |
| CN109674803A (en) * | 2018-12-21 | 2019-04-26 | 奥美医疗用品股份有限公司 | Antibacterial agent, antibacterial pure cotton non-woven fabrics and its preparation method and application |
| CN109837739A (en) * | 2019-03-05 | 2019-06-04 | 广州市雅娜琪服装有限公司 | A kind of preparation process of antibacterial wool knitting fabric |
| CN112047976B (en) * | 2020-09-11 | 2022-12-27 | 苏州东杏表面技术有限公司 | Fluorine-containing organosilicon quaternary ammonium salt and preparation method and application thereof |
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