CN102059096A - Non-woven surface covalent bonding gelatin adsorption material and preparation method thereof - Google Patents
Non-woven surface covalent bonding gelatin adsorption material and preparation method thereof Download PDFInfo
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- CN102059096A CN102059096A CN201010559736.4A CN201010559736A CN102059096A CN 102059096 A CN102059096 A CN 102059096A CN 201010559736 A CN201010559736 A CN 201010559736A CN 102059096 A CN102059096 A CN 102059096A
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- gelatin
- nonwoven
- covalent bonding
- compounds
- tannin
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Links
- 229920000159 gelatin Polymers 0.000 title claims abstract description 107
- 239000008273 gelatin Substances 0.000 title claims abstract description 107
- 235000019322 gelatine Nutrition 0.000 title claims abstract description 107
- 235000011852 gelatine desserts Nutrition 0.000 title claims abstract description 107
- 108010010803 Gelatin Proteins 0.000 title claims abstract description 105
- 239000000463 material Substances 0.000 title claims abstract description 65
- 238000002360 preparation method Methods 0.000 title claims description 16
- 238000001179 sorption measurement Methods 0.000 title abstract description 29
- 229920001864 tannin Polymers 0.000 claims abstract description 52
- 239000001648 tannin Substances 0.000 claims abstract description 52
- 235000018553 tannin Nutrition 0.000 claims abstract description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229920001155 polypropylene Polymers 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000004745 nonwoven fabric Substances 0.000 claims abstract description 10
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- 238000010521 absorption reaction Methods 0.000 claims description 28
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- 239000000243 solution Substances 0.000 claims description 23
- 229920005989 resin Polymers 0.000 claims description 22
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- 238000000576 coating method Methods 0.000 claims description 21
- 239000011248 coating agent Substances 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 17
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 13
- 239000004800 polyvinyl chloride Substances 0.000 claims description 13
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 claims description 12
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- 238000007654 immersion Methods 0.000 claims description 10
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- 239000007864 aqueous solution Substances 0.000 claims description 9
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- 235000013824 polyphenols Nutrition 0.000 claims description 8
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
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- 239000002904 solvent Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052794 bromium Inorganic materials 0.000 claims description 4
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- 238000010168 coupling process Methods 0.000 claims description 4
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- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 abstract 1
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 25
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- 108010035532 Collagen Proteins 0.000 description 3
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- 229920002755 poly(epichlorohydrin) Polymers 0.000 description 3
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- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 2
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- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- SYUXAJSOZXEFPP-UHFFFAOYSA-N glutin Natural products COc1c(O)cc2OC(=CC(=O)c2c1O)c3ccccc3OC4OC(CO)C(O)C(O)C4O SYUXAJSOZXEFPP-UHFFFAOYSA-N 0.000 description 2
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- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention discloses a method for preparing a novel adsorption material by covalent bonding gelatin on the surface of a non-woven fabric, comprising the following steps of, with a synthetic or nature high polymer non-woven fabric (such as PP (Propene Polymer), PET (Polyester Terephthalate), cellulose and the like) as a substrate, dip-coating the synthetic or nature high polymer non-woven fabric with a polyazide solution to form an activated non-woven fabric substrate, and dip-coating a gelatin solution on the activated non-woven fabric substrate; and utilizing ultraviolet irradiation to photolyze an azide group to form active nitrene, covalently bonding gelatin molecules on the surface of the non-woven fabric through insertion reaction of the active nitrene, and generating partial crosslinking, and finally, removing unbonded or uncrosslinked gelatin by soaking with cold or hot water to prepare the adsorption material. The adsorption material prepared by the method disclosed by the invention has stronger adsorption capacity to tannin, has the balance adsorption capacity of 59.5-134.2mg/g and can reach adsorption balance through about 3h.
Description
Technical field
The present invention relates to a kind of fiber adsorbing material at nonwoven surface covalent bonding gelatin the preparation method and to the absorption of tannin with separate.
Background technology
Tannin claims plant polyphenol again, is a kind of chemical composition in the plant, and special odor is arranged, it is extremely puckery to distinguish the flavor of, and certain bio-toxicity is arranged, and tannin is excessive in the food can suppress digestive enzyme activity, reduce the absorption of human body, cause enterogastritis, alimentary canal hyperemia and hepatic injury vitamin, mineral matter and protein.The contained tannin of injection then has a strong impact on its security and stability, can cause solidifying of protein in the blood, causes the redness at patient injection position, can cause arrhythmia cordis when serious, bring out and increase the weight of heart failure and cause death; Phenomenons such as the medicine that contains tannin often makes that feeling sick appears in the patient, diarrhoea and headache; When plant polyphenol content was higher in the beer fruit juice, easy and contained activated protein effect and the generation of generation precipitation were muddy, and then shortened the shelf life of these class commodity; Tannin can form yellowish-brown curtain coating thing and introduce assorted flavor in water body, betide in supply water surface and the shallow well water quality is reduced.Therefore, the technology that removes from the aqueous solution from tannin has all caused extensive concern.
The method that removes tannin mainly contains gelatin precipitation/imvite absorption method, the heavy metal ion precipitation method, macroreticular resin absorbing method, electrochemical oxidation process, photocatalytic degradation method and adsorbents adsorb method etc.Utilize the interaction between glutin and the polyphenol, play muddy active polyphenol in the precipitable beverage of aqueous gelatin solution, remove by filter gelatin-tannin sediment after, remove unnecessary gelatin with adsorbents such as imvite, bentonites again.But can reduce the quality and the storage stability of product, and the tiny filtration resistance of precipitate particles is big.Some heavy metal ion (Fe
3+, Cu
2+, Pb
4+Deng) under specific pH value, can form polynuclear complex with the polyhydroxy phenol in the tannin, produce flocculent deposit and remove tannin, but can in product, introduce heavy metal ion.With macroporous absorbent resin adsorbing separation tannin, its adsorption capacity is lower, and equilibrium adsorption capacity is low to moderate 2.7mg/g, and tannin easily enters the internal layer matrix of resin, and adsorption effect is subjected to tannin kind and plant regional effect of living in bigger.Electrochemical oxidation process is that the HO that utilizes ferroelectric utmost point reaction to produce makes tannic acid oxidized, but intermediate product may cause secondary pollution, also can be at the simultaneous oxidation useful component of oxidation tannin.Photocatalytic degradation makes tannin degraded and removes with UV light irradiation normally in the presence of the load photoactive catalyst, also causes secondary pollution and consuming time longer easily in product.Adsorbing and removing is the tannin removal methods of using always, but in traditional adsorbent, active carbon is subject to the shortage of its specific area, surface charge savings ability and specific adsorption active sites, and adsorption capacity is also very low, can only remove the tannin of low concentration.The PVPP resin has the nitrogenous five-membered ring and the amido link of evacuation, have with tannin special interactional active sites takes place, alternative is adsorbed plant polyphenol, but only limits to be rich in the beverage of polyphenol, be not suitable for the beverage that is rich in protein, cost an arm and a leg and flushing speed slow.Chinese patent 02134173.7 disclosed collagen fiber adsorption material utilizes the special interaction of collagen and tannin molecule, can realize that the selective absorption of tannin removes, but exists animal skins to supply with and problem such as materials ' durability is limited.
Summary of the invention
The present invention is for overcoming the deficiencies in the prior art, a kind of nonwoven surface covalent bonding gelatin sorbing material and preparation method thereof is proposed, be characterized in that with the macromolecule nonwoven be base material, the UV coupling technology of getting involved by many triazo-compounds is covalently bonded to nonwoven surface with gelatin molecule, and the sorbing material of making can remove tannin effectively.
The present invention in the technical scheme of the novel absorption material of nonwoven surface covalent bonding gelatin preparation is: this material is a carrier with the macromolecule nonwoven, the UV coupling technology of getting involved by many triazo-compounds is covalently bonded to nonwoven surface with gelatin molecule, utilize ultraviolet light irradiation to make the azido group photodissociation become active nitrence, it inserts reaction, and that gelatin molecule is covalently bound to the concurrent first portion of nonwoven surface is crosslinked, after cold or hot-water soak remove not bonding or uncrosslinked gelatin and make described sorbing material.
A kind of novel absorption material in nonwoven surface covalent bonding gelatin preparation can be used for industries such as plant extracts and chemical industry, food, medicine and water improvement and contains absorption, extraction that tannin is a tannin in the plant polyphenol aqueous solution and the waste water, separates and remove.
A kind ofly prepare the method for a class novel absorption material, the method is characterized in that and contain following steps at nonwoven surface covalent bonding gelatin:
(1), utilize polydentate compound or Halogen macromolecule resin and Sodium azide be substituted the reaction and purification process make the photoactive many triazo-compounds of UV;
(2), many triazo-compounds solution impregnation is coated on the nonwoven surface, make it to form and contain the photoactive many triazo-compounds coating of UV ultraviolet, immersion coating gelatin solution and form gelatin coating more thereon behind the surface drying;
(3), with the nonwoven (containing many triazo-compounds of one deck coating and one deck gelatin coating at least) after the above-mentioned immersion coating processing, place irradiation under the uviol lamp, making the azido group photodissociation is active nitrence, and nitrence and nonwoven and gelatin reaction take place to insert and make gelatin molecule partial cross-linked and be covalently bonded to nonwoven surface;
(4), the operation of (2) (3) can repeat repeatedly, can carry out also can not carrying out UV irradiation between each repetitive coatings, and then realize regulation and control gelatin bonding effect and supported quantity n;
(5), above-mentioned irradiation product soaked in room temperature water or hot water removes not bonding or uncrosslinked gelatin, promptly make nonwoven surface covalent bonding gelatin sorbing material.
Described nonwoven is polypropylene (PP) nonwoven, polyester (PET) nonwoven, polyvinyl alcohol (PVA) nonwoven, polyimide nonwoven fabric, cellulosic nonwoven fabric and azelon nonwoven.
Described many triazo-compounds are the many halogen compounds or the macromolecule resins of chloride (Cl) or bromine (Br), as polyhalohydrocarbon and Hydrin, polyvinyl chloride and vinyl chloride-vinyl acetate resin, or wherein several mixtures.
Described many triazo-compounds solution, its preparation solvent is carrene, chloroform, dichloroethanes, oxolane, dioxane, NN dimethyl formamide (DMF), formamide, acetonitrile and water, or wherein several mixtures.
Principle of the present invention is: (1) utilizes modern industry mass producible macromolecule nonwoven to be the inertia base material, speciality for sorbing material is given the fiber-like adsorbent obtains the flexibility of intensity, durability, high osmotic stability, micron-sized strainability and end product form; (2) the UV light coupling activity that utilizes many triazo-compounds merges the gelatin molecule covalent bond and is fixed in nonwoven surface, for sorbing material is given selective absorption function to tannin.Gelatin is the protein that extracts from animal collagen, and tannin easily and specific protein-polyphenol hydrogen bond takes place for wherein proline, glycine and glutamic acid units and hydrophobic cooperative interaction is effectively adsorbed.The sterically hindered Xiao Yi of glycine combines with tannin generation hydrogen bond, and proline makes gelatin molecule present variable and open space structure, can strengthen the affinity between gelatin and tannin.The application of in traditional tannin tanning and beer clarification technology, having succeeded of this principle; (4) can control bonding effect and the supported quantity of gelatin by the adjustment of coating and UV irradiation technique and condition in nonwoven surface, and then the adsorption capacity of regulation and control sorbing material.
The concrete characteristics of this method are: (1) soaks nonwoven with drying for standby after removing impurity such as surperficial grease, processing aid in solvent (as acetone, ethanol, water etc.), many triazo-compounds are dissolved in solvent (in carrene, oxolane, DMF or water) wiring solution-forming, gelatin is made into the aqueous solution; (2) many triazo-compounds of difference immersion coating one deck solution on nonwoven, immersion coating one deck gelatin solution again behind the surface drying, place irradiation under the uviol lamp, aforesaid operations can repeat nonwoven behind the surface drying repeatedly to regulate the bonding effect and the supported quantity of nonwoven surface gelatin; (3) above-mentioned irradiation product is soaked in room temperature water or hot water remove not bonding or uncrosslinked gelatin, promptly make nonwoven surface covalent bonding gelatin sorbing material, effectively the tannin in the adsorption aqueous solution; (4) used many triazo-compounds are by many halogen (Cl or Br) compound or Halogen (Cl or Br) macromolecule resin (as Hydrin, polyvinyl chloride and vinyl chloride-vinyl acetate resin) and Sodium azide generation substitution reaction and purified making.
The advantage of this method and described novel absorption material is: whether the many triazo-compounds nitrence insertion under (1) UV light is auxiliary has active group not require at nonwoven surface chemical bonding gelatin to base material, and wide adaptability is workable; (2) after gelatin is fixed in nonwoven surface by chemical bonding/crosslinked, nonwoven provides mechanical performance and big specific area, the bonding gelatin then provides adsorption function, get the effect of composite property complementation, can overcome the problems such as water-soluble, frangible and filter operation difficulty that gelatin self exists as adsorbent simultaneously; (3) but the wide ranges of bonding gelatin amount on the nonwoven, also can be by regulating the gelatin supported quantity, the control sorbing material is to the adsorption capacity of tannin; (4) utilize that the nonwoven specific area is big, osmotic stability is high, cross the little characteristics of column resistance, realize absorption of serialization column chromatography and separating technology easily tannin; (5) raw material sources of sorbing material are extensive, and manufacturing process is easy, can be widely used in tannin in the fields such as chemical industry, food, medicine, natural products and water improvement absorption, extraction, separate and remove.
Description of drawings
Fig. 1 is the FTIR spectrogram (embodiment 1) of Hydrin and poly-nitrine glycidol ether
Fig. 2 is the FTIR spectrogram (embodiment 2) of polyvinyl chloride and nitrine polyvinyl chloride
Fig. 3 is the FTIR spectrogram (embodiment 3) of vinyl chloride-vinyl acetate resin and nitrine vinyl chloride-vinyl acetate resin
Fig. 4 is the FTIR spectrogram (embodiment 7) of nonwoven surface covalent bonding gelatin sorbing material (poly-nitrine glycidol ether system).1 is the PP nonwoven among Fig. 4, and 2 is gelatin, and 3 is sorbing material.
Fig. 5 is the FTIR spectrogram (embodiment 11) of nonwoven surface covalent bonding gelatin sorbing material (nitrine polyvinyl chloride system), and 1 is the PP nonwoven among Fig. 5, and 2 is gelatin, and 3 is sorbing material.
Fig. 6 is the FTIR spectrogram (embodiment 14) of nonwoven surface covalent bonding gelatin sorbing material (nitrine vinyl chloride-vinyl acetate resin alkene system), and 1 is the PP nonwoven among Fig. 6, and 2 is gelatin, and 3 is sorbing material.
Fig. 7 (A) is the SEM photo (PP nonwoven) of nonwoven surface covalent bonding gelatin sorbing material.
Fig. 7 (B) is the SEM photo (embodiment 5) of nonwoven surface covalent bonding gelatin sorbing material.
Fig. 7 (C) is the SEM photo (embodiment 8) of nonwoven surface covalent bonding gelatin sorbing material.
Fig. 7 (D) is the SEM photo (embodiment 13) of nonwoven surface covalent bonding gelatin sorbing material.
Scale is represented 20 μ m, multiplication factor 2000 among Fig. 7 (A, B, C, D).
Fig. 8 (A) is the adsorption capacity of sorbing material and the graph of a relation (embodiment 15) of adsorption time and tannin original liquid concentration.Wherein sorbing material is taken from embodiment 4, tannin stoste volume 50mL, sorbing material inventory 0.1g, 24 ℃ of adsorption temps.
Fig. 8 (B) is the adsorption capacity of sorbing material and the graph of a relation (embodiment 15) of adsorption time and tannin original liquid concentration.Wherein sorbing material is taken from embodiment 10, tannin stoste volume 50mL, sorbing material inventory 0.1g, 24 ℃ of adsorption temps.
The specific embodiment
The present invention will be further described in detail below in conjunction with the drawings and specific embodiments.
The present invention in turn includes the following steps: (1) is substituted polydentate compound or Halogen macromolecule resin and Sodium azide the many triazo-compounds that make the UV activity behind reaction and the purifying; (2) nonwoven is soaked in solvent to remove dried for standby behind the impurity such as surperficial grease, processing aid, many triazo-compounds and gelatin wiring solution-forming are stand-by; (3) many triazo-compounds of difference immersion coating one deck solution on nonwoven, immersion coating one deck gelatin solution again behind the surface drying, place irradiation under the uviol lamp, aforesaid operations can repeat nonwoven behind the surface drying repeatedly to regulate the bonding effect and the supported quantity of gelatin on the nonwoven; (4) above-mentioned irradiation product is placed room temperature water or hot water soak and remove not bonding or uncrosslinked gelatin, promptly make nonwoven covalent bonding gelatin sorbing material; (5) the gained sorbing material is dropped into the tannin aqueous solution, stir adsorbing and removing tannin down.
The preparation of embodiment 1 (1) Hydrin (PECH) is with refining
Mounting strap has the there-necked flask of mechanical agitator, nitrogen conduit and condenser pipe in water-bath.Order adds 4mL and makes with extra care 1,2-dichloroethanes and 0.4mL 1, and the 2-propane diols starts and stirs also feeding drying nitrogen.With the anhydrous SnCl of 0.5mL
4Be injected under the liquid level, in 40min, drip 65mL epoxychloropropane (ECH) then.Stir polymerisation 24h down at 30 ℃.Reaction is finished the back and is added the dilution of 40～50mL carrene, changes separatory funnel over to and washs several to water with 5% hot salt brine and be pH neutrality.Behind the standing demix lower floor's organic facies is placed the beaker that is added with molecular sieve, at silica gel drier inner drying 24h.Filter then, filtrate decompression distillation 1h in 150 ℃ of oil baths removes volatile matter, gets light yellow sticky thing and is refining PECH.Its FTIR spectrogram is seen Fig. 1 spectral line 1, and characteristic absorption is with identical with literature value.
(2) preparation of poly-nitrine glycidol ether (GAP) is with refining
5g PECH is put into four-hole boiling flask, add the refining DMF of 35mL, soak behind the certain hour heating for dissolving in 100 ℃ of oil baths.Add anhydrous LiCl of 0.15g and 7.15g NaN respectively
3, feed drying nitrogen stirring reaction 5h down in 100 ℃ and be obviously faint yellow to reaction mass.Filter to such an extent that GAP clarifies glue behind the cool to room temperature.With 150mL absolute methanol precipitation, 24-48h is left standstill in the sealing back in 5 ℃ of refrigerators.Precipitation is back sucking-off supernatant fully, and the yellow glue in bottom is the GAP crude product.Crude product is earlier with 60 ℃ of distilled water agitator treatings 4-5 time, reusable heat methanol wash 2 times, and jelly is creamy white, and places silica gel drier lucifuge drying 24h.Dry back colloid is refining GAP by the leucismus Huang, and it is standby to keep in Dark Place in 5 ℃ of refrigerators.Its FTIR spectrogram is seen Fig. 1 spectral line 2, and characteristic absorption and literature value coincide.
Embodiment 2: get the 8g Sodium azide and the 0.17g TBAB is gone into beaker, add the 25.3mL dissolved in distilled water and promptly get sodium azide aqueous solution.
In there-necked flask, add 0.2g polyvinyl chloride (commercially available 5 types), add the above-mentioned sodium azide aqueous solution of 16.7mL, stirring reaction 4h in 80 ℃ of oil baths, back then with a large amount of distilled water and 10mL methyl alcohol difference washing and filtering, filter residue is nitrine polyvinyl chloride crude product.Crude product is earlier with the dissolving of 10mL oxolane, uses suction filtration behind the 30mL methanol extraction again, and three times and dry the nitrine product that promptly gets purifying repeatedly, it is standby to keep in Dark Place in 5 ℃ of refrigerators.Its FTIR spectrogram is seen Fig. 2 spectral line 2, and characteristic absorption and literature value coincide, and the FTIR spectrogram of Corvic is seen Fig. 2 spectral line 1.
Embodiment 3: repeat embodiment 2 and only polyvinyl chloride is changed into vinyl chloride-vinyl acetate resin (commercially available CM1133 type), its FTIR spectrogram is seen Fig. 3 spectral line 1, and characteristic absorption is with identical with literature value, and the FTIR spectrogram of vinyl chloride-vinyl acetate resin is seen Fig. 3 spectral line 2.
From the FTIR spectrogram (Fig. 1-Fig. 3 spectral line 2) of the prepared many triazo-compounds of embodiment 1-3, can find that azido reaction does not influence the characteristic absorption of chlorine-containing polymer resin backbone structure, only make 700-750.0cm
-1The place belongs to CH
2The strong stretching vibration peak of-Cl disappears or weakens, and at 2100-2112cm
-1Strong belonging to-N then appears in the place
3The absworption peak of the asymmetric stretching vibration of group, the appearance of the minimizing of chlorine atom and nitrine characteristic peak confirms that azido group has replaced chlorine ,-N
3Successfully be incorporated on the side chain of corresponding chlorine-containing polymer.
Embodiment 4: the poly-nitrine glycidol ether 0.05g of embodiment 1 gained is dissolved in carrene is made into the solution that concentration is 8.3g/L, with gelatin (commercially available Type B one-level skin edible gelatin, isoelectric point 5.5-7.0) the 2g concentration that is made into soluble in water is 16.7% solution for standby.Cutting out a collection of diameter is circular PP nonwoven (commercially available industrial nonwoven, the 8-10g/m of 8cm
2), place acetone to soak 1h to remove surperficial grease and polymerization inhibitor, standby after taking out in drying in oven.
Behind PP nonwoven surface immersion coating one strata nitrine glycidol ethereal solution, dry, dry in the dark place after applying one deck gelatin solution more thereon then in the dark place.Surface drying is placed on the 15cm irradiation 20min that keeps at a distance under the 15w uviol lamp, promptly gets PP nonwoven bonding gelatin crude product.Crude product is soaked in that 1h promptly gets PP nonwoven bonding gelatin sorbing material to remove not bonding or uncrosslinked gelatin in 60 ℃ of hot water after the drying, and its gelatin supported quantity n is 0.86g/g.
Embodiment 5: repetition embodiment 4 only will gather nitrine glycidol ether solution concentration and change 12.5g/L into, and its gelatin supported quantity n is 1.14g/g, and SEM (SEM) photo is seen Fig. 7 (2)
Embodiment 6 is dissolved in the poly-nitrine glycidol ether 0.05g of embodiment 1 gained in the carrene, is made into the solution that concentration is 12.5g/L, is 16.7% solution for standby with the gelatin 2g concentration that is made into soluble in water.Cutting out a collection of diameter is the circular PP nonwoven of 8cm, places acetone to soak 1h to remove surperficial grease and polymerization inhibitor, standby in drying in oven after taking out.
Behind PP nonwoven surface immersion coating one strata nitrine glycidol ethereal solution, dry, dry in the dark place after applying one deck gelatin solution more thereon then in the dark place.Surface drying is placed on the 15cm irradiation 30min that keeps at a distance under the 15w uviol lamp.Repeating aforementioned operation once, promptly get PP nonwoven bonding gelatin crude product.Crude product is soaked in removes not bonding or uncrosslinked gelatin among 60 ℃ of hot water 1h, promptly get PP nonwoven surface bonding gelatin sorbing material after the drying, its gelatin supported quantity n is 3.20g/g.
Embodiment 7: repeat embodiment 6, only change nitrine glycidol ether concentration into 8.3g/L, soaking conditions changes room temperature water into and soaks 24h, and its gelatin supported quantity n is 4.55g/g, and the FTIR spectrogram is seen Fig. 4.
Embodiment 8: repeat embodiment 4, only triazo-compound is changed into embodiment 2 gained nitrine polyvinyl chloride, use the oxolane obtain solution instead, concentration changes 10g/L into, and its gelatin supported quantity n is 1.21g/g, and SEM (SEM) photo is seen Fig. 7 (3).
Embodiment 9: repeat embodiment 6, only triazo-compound is changed into embodiment 2 gained nitrine polyvinyl chloride, use the oxolane obtain solution instead, concentration changes 10g/L into, and its gelatin supported quantity n is 3.07g/g.
Embodiment 10: repeat embodiment 9, its gelatin supported quantity n is 3.16g/g.
Embodiment 11: repeat embodiment 6, only triazo-compound is changed into embodiment 2 gained nitrine polyvinyl chloride, use the oxolane obtain solution instead, concentration changes 10g/L into, soaking conditions changes room temperature water into and soaks 24h, and its gelatin supported quantity n is 5.59g/g, and the FTIR spectrogram is seen Fig. 5.
Embodiment 12: repeat embodiment 8, only triazo-compound is changed into embodiment 3 gained nitrine vinyl chloride-vinyl acetate resins, its gelatin supported quantity n is 1.29g/g.
Embodiment 13: repeat embodiment 9, only triazo-compound is changed into embodiment 3 gained nitrine vinyl chloride-vinyl acetate resins, its gelatin supported quantity n is 2.75g/g, and SEM (SEM) photo is seen Fig. 7 (3).
Embodiment 14: repeat embodiment 11, only triazo-compound is changed into embodiment 3 gained nitrine vinyl chloride-vinyl acetate resins, its gelatin supported quantity n is 5.44g/g, and the FTIR spectrogram is seen Fig. 6.
In the FTIR spectrogram (Fig. 4-6) of embodiment 7,11 and 14 prepared nonwoven surface covalent bonding gelatin sorbing materials, curve 1 is the infrared line of PP nonwoven, and curve 2 is infrared lines of gelatin, 3491.6cm
-1There is strong broad peak at the place, belongs to the flexible or O-H stretching vibration of N-H in the characteristic absorption band of amide groups in the gelatin, in the glutin molecule and intermolecular hydrogen bond causes the peak molded breadth big.1651.4cm
-1Place's absworption peak belongs to C=O stretching vibration or CN stretching vibration in the acid amides I band secondary amide, 1538.0cm
-1Place's absworption peak then belongs to the coupling of acid amides II band-N-H flexural vibrations and CN stretching vibration, 1090cm
-1V peak, place then belongs to C-N-C stretching vibration or C-O stretching vibration.Spectral line 3 from Fig. 4-6 can find that nonwoven surface covalent bonding gelatin sorbing material is at 1653.8cm
-1, 1534.1cm
-1And 1092.8cm
-1Corresponding characteristic absorption peak has all appearred in the acid amides characteristic absorption I at place, II, V band, confirms that gelatin molecule really is introduced into the PP nonwoven surface.
From nonwoven and embodiment 5, the SEM photo (Fig. 7) of 8 and 13 prepared nonwoven surface covalent bonding gelatin sorbing materials can be found, the pattern of UV exposure light bonding gelatin reaction change PP fiber, cause the PP fibre thickening rough, tangible attachment has appearred on the fiber, average fibre diameter increases to 25.5 μ m (embodiment 5), 29.3 μ m (embodiment 8) and 31.4 μ m (embodiment 13) respectively by 22.2 μ m (PP nonwoven), and this order also matches with the order that sorbing material gelatin supported quantity n increases.The above-mentioned variation that PP fiber surface pattern takes place illustrate intuitively the PP nonwoven surface bonding gelatin molecule.
Embodiment 15: the tannic acid aqueous solution of getting concentration 100-300mg/L, drop into certain mass by the prepared nonwoven surface bonding gelatin sorbing material of embodiment 4-embodiment 14, under magnetic agitation, carry out tannin absorption, the concentration of after absorption is finished raffinate being filtered constant volume and adopting Phen colour developing spectrophotometry stoste and adsorb tannin in the raffinate, measure the adsorption capacity (Q of each sorbing material to tannin, g tannin/g sample), the results are shown among table 1 and Fig. 8.The result shows, described sorbing material to the equilibrium adsorption capacity of tannin between 59.5mg/g-134.2mg/g, adsorption capacity is nitrine vinyl chloride-vinyl acetate resin system＞nitrine polyvinyl chloride system＞poly-nitrine glycidol ether system in proper order, is adsorbed on and reaches balance about 3h substantially.
Comparative example 1
Repeat embodiment 15, only sorbing material is changed into the PP nonwoven, measure it the adsorption capacity Q of tannin only is 5.0mg/g, show that it does not have suction-operated substantially to tannin.
Table 1PP nonwoven surface bonding gelatin sorbing material is to the adsorptivity of tannin
| Sample | n，g/g? | The tannin original liquid concentration, mg/L | Adsorption capacity Q, (mg/g) |
| Embodiment 5 | 1.14? | 213.0? | 69.0? |
| Embodiment 6 | 3.20? | 213.0? | 68.2? |
| |
4.55? | 213.0? | 65.6? |
| Embodiment 8 | 1.21? | 213.0? | 94.5? |
| Embodiment 9 | 3.07? | 213.0? | 70.3? |
| Embodiment 11 | 5.59? | 278.3? | 59.5? |
| Embodiment 12 | 1.29? | 278.3? | 134.2? |
| Embodiment 13 | 2.75? | 278.3? | 121.5? |
| Embodiment 14 | 5.44? | 278.3? | 73.2? |
| Comparative example | 0? | 213.0? | 5.0? |
Annotate: tannin stoste volume 100mL, sorbing material throwing amount 0.2g, adsorption time and temperature 24h/ room temperature.
Claims (6)
1. novel absorption material in nonwoven surface covalent bonding gelatin preparation, it is characterized in that: this material is a carrier with the macromolecule nonwoven, the UV coupling technology of getting involved by many triazo-compounds is covalently bonded to nonwoven surface with gelatin molecule, utilize ultraviolet light irradiation to make the azido group photodissociation become active nitrence, it inserts reaction, and that gelatin molecule is covalently bound to the concurrent first portion of nonwoven surface is crosslinked, after cold or hot-water soak remove not bonding or uncrosslinked gelatin and make described sorbing material.
2. administer industry and contain absorption, extraction that tannin is the plant polyphenol aqueous solution and waste water tannin, separate and remove application as being used for plant extracts and chemical industry, food, medicine and water at the novel absorption material of nonwoven surface covalent bonding gelatin preparation.
3. method at the novel absorption material of nonwoven surface covalent bonding gelatin preparation is characterised in that and contains following steps: (1), utilize polydentate compound or Halogen macromolecule resin and Sodium azide to be substituted to react and purification process makes the photoactive many triazo-compounds of UV;
(2), many triazo-compounds solution impregnation is coated on the nonwoven surface, make it to form and contain the photoactive many triazo-compounds coating of UV ultraviolet, immersion coating gelatin solution and form gelatin coating more thereon behind the surface drying;
(3), with the nonwoven (containing many triazo-compounds of one deck coating and one deck gelatin coating at least) after the above-mentioned immersion coating processing, place irradiation under the uviol lamp, making the azido group photodissociation is active nitrence, and nitrence and nonwoven and gelatin reaction take place to insert and make gelatin molecule partial cross-linked and be covalently bonded to nonwoven surface;
(4), the operation of above-mentioned steps (2), (3) can repeat repeatedly, carry out between each repetitive coatings/do not carry out UV irradiation, and then finish regulation and control gelatin bonding effect and supported quantity n;
(5), above-mentioned irradiation product soaked in room temperature water or hot water removes not bonding or uncrosslinked gelatin, promptly make nonwoven surface covalent bonding gelatin sorbing material.
4. according to the method for the tencel sorbing material of the described nonwoven surface covalent bonding gelatin preparation of claims 3, it is characterized in that described nonwoven is polypropylene (PP) nonwoven, polyester (PET) nonwoven, polyvinyl alcohol (PVA) nonwoven, polyimide nonwoven fabric, cellulosic nonwoven fabric and azelon nonwoven.
5. according to the method for the novel absorption material of the described nonwoven surface covalent bonding gelatin preparation of claims 3, it is characterized in that described many triazo-compounds are the many halogen compounds or the macromolecule resins of chloride (Cl) or bromine (Br), as polyhalohydrocarbon and Hydrin, polyvinyl chloride and vinyl chloride-vinyl acetate resin, or wherein several mixtures.
6. according to the method for the novel absorption material of the described nonwoven surface covalent bonding gelatin preparation of claims 3, it is characterized in that described many triazo-compounds solution, its preparation solvent is carrene, chloroform, dichloroethanes, oxolane, dioxane, NN dimethyl formamide (DMF), formamide, acetonitrile and water, or wherein several mixtures.
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| CN103061106A (en) * | 2012-12-31 | 2013-04-24 | 东华大学 | Low-carbon photocuring single-side moisture transport finishing agent as well as preparation method and application thereof |
| CN103263898A (en) * | 2013-05-20 | 2013-08-28 | 昆明理工大学 | Material of non-woven fabric surface heavy nitrogen coupling gelatin adsorbing material and preparation method thereof |
| CN104549178A (en) * | 2014-12-18 | 2015-04-29 | 昆明理工大学 | Adsorbing material for azide method coupling gelatin and preparation method of adsorbing material |
| CN112593342A (en) * | 2020-12-04 | 2021-04-02 | 上海即索实业有限公司 | Kapok and copper ammonia fiber blended mask cloth and manufacturing method thereof |
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| CN112593342A (en) * | 2020-12-04 | 2021-04-02 | 上海即索实业有限公司 | Kapok and copper ammonia fiber blended mask cloth and manufacturing method thereof |
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