CN101403143B - Method for producing fluorescent polypropylene fibers by utilizing organic fluorescent compound - Google Patents
Method for producing fluorescent polypropylene fibers by utilizing organic fluorescent compound Download PDFInfo
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Abstract
The invention relates to a method for preparing fluorescent polypropylene fiber by adopting organic fluorescent compound. The method comprises the following steps: (1) salicylic aldehyde and derivatives of salicylic aldehyde are dissolved in absolute ethyl alcohol and heated to 70 to 100 DEG C in water bath, ethanol solution of diamine compound is added in drips, after condensing reflux and standing, brilliant yellow, orange or red precipitate can be obtained, and the precipitate is filtered, re-crystallized by ethanol, pump filtered and dried, thus obtaining the organic fluorescent compound;(2) polypropylene, the fluorescent compound and fluorescent additive are mixed uniformly, and melt blending, extruding and spinning are carried out by a multifilament 400 melting and spinning machine, the spinning speed is 400m/min, the spinning temperature is 270 DEG C, the after-drawing ratio is 2.8 times, and the fluorescent polypropylene fiber can be obtained. The preparing method is simple, and the yield is high; the obtained fluorescent compound has good solid luminescent property, non-toxicity, non-radioactivity, uniform dispersion in high polymer of polypropylene and good spinnability, and good luminescent effect can be obtained by only adding less than 1 percent of the fluorescent polypropylene fiber.
Description
Technical field
The invention belongs to the Preparation of Fluorescent Material field, particularly relate to a kind of method that adopts organic fluorescent compounds to prepare the fluorescence polypropylene fibre.
Background technology
Fluorescent material is commonly called as fluorescent material, all is widely used in fields such as industry, agricultural, medical science, national defence.Can be used as fluorescent whitening agent, fluorescent dye, fluorescent pigment, fluorometric reagent, laser dye, be used for anti-counterfeiting technology, the scintillator in fluorescence analysis, tracking detection, traffic sign, the nuclear technology, the fluorescence optical collector in the solar energy switch technology etc.At present, high performance fluorescent material all is some inorganic salt compounds or metal ion match usually, and seldom has organic compound to report as the high-performance phosphor compounds.This is because most organic fluorescence materials only have the good fluorescence performance but under solid-state situation, but show very poor fluorescence in solution.Therefore explore the novel solid luminescent material of preparation and be applied to prepare the high-performance luminescent fibre and also become a challenge problem gradually.
The fluorescence falsification preventing fiber is claimed safety fibre again, and it can be divided into IR fluorescence anti-false fiber and Ultraluminescence anti-false fiber.The IR fluorescence anti-false fiber is meant that (wavelength excites a kind of novel anti-false fiber that can launch multiple different colours (red, blue, green, yellow green) down 0.7～1.6m) usually at infrared light.Ultraviolet fluorescent fiber is meant the brilliance that under ultraviolet excitation, can glimmer, and can launch various color, after ultraviolet light disappears, can be returned to the fiber of primary colors again.Fluorescent fiber can be widely used in false proof field, like certificate, bill, trade mark etc.Generally fluorescent fiber is cut off, be randomly dispersed in the paper pulp, make anti-forge paper.These false proof certificates, bill, trade mark can send the light of different colours under ultraviolet excitation, reach false proof purpose.
The fluorescent fiber preparation method adds fluorescent chemicals in the fiber-forming polymer to, processes fiber then.The spinning method for genuine of fluorescent fiber has a lot, is broadly divided into following several kinds: melt spinning method, solution spinning, face coat method etc.Diverse ways requires emphasis different to production technology and Ultraluminescence compound.Melt spinning method requires the fluorescent chemicals resistance to oxidation sun-resistant, high temperature resistant; Solution spinning requires fluorescent chemicals can be dissolved in the spinning solution; Face coat method technology is fairly simple, but receives environmental limit when using.If it is improper to select, can cause the part fluorescent particles to be in the surperficial or poor of fiber with the compatibility of fibre-forming polymer, the mechanical performance of goods anti-false fiber is descended, very easily weaken even lose the function of fluorescence falsification preventing.
Chinese invention patent prospectus (CN1092119A for example; Safety fibre in the used anti-forge paper such as a kind of marketable securities application number 93102550.8), certificate, this fiber with mixed with polymers such as fluorescent material (content is 0.3%-6.0%) and polyvinyl alcohol after spinning obtain staple fibre.But this concentration is not enough to obtain higher aura degree, even and luminescent material concentration be no more than 6%, this fiber also is difficult to process and can directly be used for woven long filament, and the intensity of this fiber and processing characteristics are relatively poor, can not be used as textile raw material.In order to overcome above-mentioned difficulties; Someone has invented a kind of ultraviolet fluorescent fibre (CN1328177; Application number 00118517.9); Adopt the mixture of rare earth elements europium and strontium aluminate to make the ultraviolet fluorescent material, rely on the fineness that reduces the fluorescence master batch to increase processability, increase fluorescent material content and improve the aura degree.But because fluorescent material contains rare earth ion, its cost is relatively high with processing Chengdu.Patent CN1817984 discloses a kind of coating that can be luminous, and this coating is light-accumulating powder by the 30-45% strontium aluminate, and the carrier of reflective powder of the refractive power of 10-15% and 40-60% is formed.Coating or printing method are simple relatively, are applicable to multiple fiber and fabric, and shortcoming is that the fluorescent material addition is big, and cost is high, is easy to peel off, and service life is shorter.
At present, be simple and easy to such an extent that the organic solid-state fluorescent material still lacks very much, rarely have document and patent report about the charge transfer type fluorescent dye of D-π-A configuration and the application in luminescent fibre thereof.
Summary of the invention
Technical problem to be solved by this invention provides a kind of method that adopts organic fluorescent compounds to prepare the fluorescence polypropylene fibre; The preparation method is simple; Productive rate is high, and is easily separated, and purity is high; The solid luminescent performance of gained fluorescent chemicals is good, can be through changing the glow color that molecular structure comes regulating compound.
A kind of method that adopts organic fluorescent compounds to prepare the fluorescence polypropylene fibre of the present invention comprises:
(1) take by weighing 1～3g salicylide and derivative thereof and be dissolved in the absolute ethyl alcohol, water-bath is heated to 70～100 ℃, and slowly drips the ethanolic solution of 0.1～0.2g diamine compound; Condensing reflux 1～3h leaves standstill, and gets glassy yellow, orange red or red precipitate; Filtering-depositing; And with filtering behind the ethyl alcohol recrystallization, oven dry gets organic fluorescent compounds;
(2) 150～300g polypropylene and 2～5g fluorescent chemicals are mixed, carry out melt blending, extrude with multifilament 400 melt spinning machines, spinning, spinning speed 400m/min, 270 ℃ of spinning temperatures, 2.8 times of after-drawing multiples obtain the fluorescence radiation fiber.
Described salicylaldehyde derivatives structure is as being shown in (I), wherein R
1, R
2Be hydrogen atom, electron withdraw group or electron donating group, n
2Integer for 1-3.：
Described diamine compound is aromatic diamines or aliphatic diamine, concrete structure as (II) (III) shown in, n
1Integer for 0-6.
Preferred diamine compound is the 85wt% hydrazine hydrate.
Described organic fluorescent compounds structure is shown in (IV)::
Glassy yellow, orange or red solid, 76～400 ℃ of melting ranges, wherein, R is aromatic rings or aliphatic hydrocarbon, R
1, R
2Be hydrogen atom, electron withdraw group or electron donating group, n
1Be the integer of 0-10, n
2Integer for 1-3.
Described aromatic rings is that the structural formula of phenyl ring (Ph) is:
Wherein, n
1Be the integer of 0-3, n
2Integer for 1-3; Described aliphatic hydrocarbon is methylene (CH
2-) structural formula be:
Described R
1, R
2For H ,-NO
2Or-N-(C
2H
5)
2, n
1=0-6, n
2The structural formula of=1-2 is:
positive butanediamine double salicylaldehyde that contracts
Described fluorescence additive is the Schiff bases compound, is specially above-mentioned fluorescent chemicals.
Described fiber is a drafted fibre, and filament number is at 1.0-5.0dtex, tensile fiber silk specification 64～68dtex/18f, and intensity 3.59～3.83cN/dtex, maximum emission wavelength are 534nm.
The invention discloses a kind of D-π-A configuration electric charge in molecule transfer type and contain the solid luminescent material and preparation method thereof of intramolecular hydrogen bond and in the application of luminescent fibre aspect preparing.With the outstanding cavity transmission group of aromatic diamines or this type of aliphatic diamine as electron donor; Salicylide and derivative thereof with strong electrophilic ability are electron acceptor; Form compound through condensation reaction, prepared a series of solid luminescent materials (like gold-tinted, green glow, orange red light and ruddiness) with pure emission with two C=N keys.The prepared solid luminescent material of the present invention can prepare the good luminescent fibre of luminescent properties as dye adulterated in polypropylene and through melt spinning.Advantage of the present invention is very remarkable, and the organic fluorescent powder preparation is simple, nontoxic, "dead", and luminosity is high; In polypropylene, be uniformly dispersed, difficult drop-off, good spinnability, fibre strength is high, and addition is lower than 1% just can reach good illumination effect.
Beneficial effect
(1) reagent source of the present invention is convenient, and the preparation method is simple, and cost is very low, and related reaction is classical reaction, and the target product productive rate is high, and is easily separated, and purity is high;
(2) the solid luminescent performance of gained fluorescent chemicals is good, nontoxic, "dead", and glow color is pure, and can be through changing the glow color that molecular structure comes regulating compound;
(3) it is simple to prepare the method for luminescent fibre, only needs a simple blend just can obtain finely dispersed luminescent fibre through the spinning process of routine, and the addition of fluorescent chemicals is little, is lower than 1% content and can obtains good illumination effect.
Description of drawings
Fig. 1 is the synthetic route chart of fluorescent chemicals;
Fig. 2 is the structural formula of fluorescent chemicals 1;
Fig. 3 is the solid state fluorescence spectrum of fluorescent chemicals 1;
Fig. 4 is the structural formula of fluorescent chemicals 2;
Fig. 5 is the solid state fluorescence spectrum of fluorescent chemicals 2;
Fig. 6 is the structural formula of fluorescent chemicals 3;
Fig. 7 is the solid state fluorescence spectrum of fluorescent chemicals 3;
Fig. 8 is the structural formula of fluorescent chemicals 4;
Fig. 9 is the solid state fluorescence spectrum of fluorescent chemicals 4;
Figure 10 is the structural formula of fluorescent chemicals 5;
Figure 11 is the solid state fluorescence spectrum of fluorescent chemicals 5;
Figure 12 is the structural formula of fluorescent chemicals 6;
Figure 13 is the solid state fluorescence spectrum of fluorescent chemicals 6;
Figure 14 is the structural formula of fluorescent chemicals 7;
Figure 15 is the solid state fluorescence spectrum of fluorescent chemicals 7;
Figure 16 is the structural formula of fluorescent chemicals 8;
Figure 17 is the solid state fluorescence spectrum of fluorescent chemicals 8;
The photo of Figure 18 fluorescent fiber that to be fluorescent chemicals 1 obtain with the acrylic resin melt spinning.
The specific embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in the restriction scope of the present invention.Should be understood that in addition those skilled in the art can do various changes or modification to the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Embodiment 1
The fluorescent chemicals synthetic route is as shown in table 1
Table 1
(1) synthetic (n of fluorescent chemicals 1
1=0, n
2=1, R
1=R
2=H)
Take by weighing the 1.20g salicylide and be dissolved in the absolute ethyl alcohol, water-bath is heated to 80 ℃, slowly drips the 0.16g85wt% hydrazine hydrate, and condensing reflux 1.5h gets yellow mercury oxide.Filter behind the recrystallization, oven dry gets target compound 1, is the glassy yellow solid, quality 1.20g (productive rate 88.6%).
Mass spectrum (EI): m/z240
Fusing point: 219 ℃
Nucleus magnetic hydrogen spectrum
1H-NMR (400MHz, CDCl
3, 25 ℃, TMS): δ=11.12 (s, 2H), 9.00 (s, 2H), 7.71-7.68 (m, 2H), 7.41 (m, 2H), 6.97 (m, 4H).Elementary analysis C
14H
12N
2O
2(240.09) calculated value: C, 69.99; H, 5.03; N, 11.66.Measured value: C, 70.05; H, 5.04; N, 11.61.(2) synthetic (n of compound 2
1=0, n
2=1, R
1=-NO
2, R
2=H)
The preparation method and 1 synthetic similar.
Mass spectrum (EI): m/z330
Fusing point:>350 ℃
Elementary analysis C
14H
10N
4O
6(330.06) calculated value: C, 50.92; H, 3.05; N, 16.96; Measured value: C, 50.90; H, 3.04; N, 16.78.
(3) synthetic (n of fluorescent chemicals 3
1=0, n
2=1, R
1=H, R
2=-N (CH
2CH
3)
2)
The preparation method and 1 synthetic similar.
Mass spectrum (EI): m/z388
Fusing point: 239 ℃
Nucleus magnetic hydrogen spectrum
1H-NMR (400MHz, CDCl
3, 25 ℃, TMS): δ=11.49 (s, 2H), 8.61 (s, 2H), 7.27 (d, 2H), 6.31 (m, 2H), 6.11 (d, 2H), 3.36 (m, 8H), 1.11 (m, 12H).
Elementary analysis C
22H
30N
4O
2(382.24) calculated value: C69.08, H7.91, N14.65; Measured value: C69.09, H7.75, N14.47.
(4) synthetic (R=-CH of fluorescent chemicals 4
2-, n
1=4, n
2=1, R
1=R
2=H)
The preparation method and 1 synthetic similar.
Mass spectrum (EI): m/z296
Fusing point: 89 ℃
Nucleus magnetic hydrogen spectrum
1H-NMR (400MHz, CDCl
3, 25 ℃, TMS): δ=13.53 (s, 2H), 8.39 (s, 2H), 7.34-7.26 (m, 4H), 6.98 (m, 2H), 6.90 (m, 2H), 3.67 (m, 4H), 1.86 (m, 4H).
Elementary analysis C
18H
20N
2O
2(296.15) calculated value: C72.95, H6.80, N9.45; Measured value: C72.67, H6.84, N9.37.
(5) synthetic (R=-CH of fluorescent chemicals 5
2-, n
1=6, n
2=1, R
1=R
2=H)
The preparation method and 1 synthetic similar.
Mass spectrum (EI): m/z324
Fusing point: 76 ℃
Nucleus magnetic hydrogen spectrum
1H-NMR (400MHz, CDCl
3, 25 ℃, TMS): δ=13.62 (s, 2H), 8.33 (s, 2H), 7.29-7.22 (m, 4H), 6.96-6.84 (m, 4H), 3.59 (m, 4H), 1.73 (m, 4H), 1.43 (m, 4H).
Elementary analysis C
20H
24N
2O
2(324.18) calculated value: C74.04, H7.46, N8.64; Measured value: C74.18, H7.657, N8.69.
(6) synthetic (R=-CH of fluorescent chemicals 6
2-, n
1=4, n
2=1, R
1=H, R
2=-N (CH
2CH
3)
2)
Mass spectrum (EI): m/z438
Fusing point: 127 ℃
Nucleus magnetic hydrogen spectrum
1H-NMR (400MHz, CDCl
3, 25 ℃, TMS): δ=11.49 (s, 2H), 8.61 (s, 2H), 7.27 (d, 2H), 6.31 (m, 2H), 6.11 (d, 2H), 3.36 (m, 8H), 1.11 (m, 12H).
Elementary analysis C
26H
38N
4O
2(438.61) calculated value: C71.20, H8.73, N12.77; Measured value: C71.40, H8.98, N12.79.
(7) synthetic (R=Ph, the n of fluorescent chemicals 7
1=1, n
2=1, R
1=R
2=H)
The preparation method and 1 synthetic similar.
Mass spectrum (EI): m/z316
Fusing point: 217 ℃
Nucleus magnetic hydrogen spectrum
1H-NMR (400MHz, CDCl
3, 25 ℃, TMS): δ=8.67 (s, 2H), 7.43-7.39 (m, 4H), 7.37 (s, 2H), 7.03 (d, 2H), 6.94 (m, 2H).
Elementary analysis C
20H
16N
2O
2(316.12) calculated value: C75.93, H5.10, N8.86; Measured value: C76.22, H5.12, N8.91.
(8) synthetic (R=Ph, the n of fluorescent chemicals 8
1=1, n
2=2, R
1=R
2=H)
The preparation method and 1 synthetic similar.
Mass spectrum (EI): m/z416
Fusing point: 311 ℃
Nucleus magnetic hydrogen spectrum
1H-NMR (400MHz, CDCl
3, 25 ℃, TMS): δ=9.46 (s, 1H), 9.33 (s, 1H), 8.20 (d, 1H), 8.12 (d, 1H), 7.81-7.74 (m, 3H), 7.56-7.52 (m, 3H), 7.42-7.37 (m, 2H), 7.30 (m, 2H), 7.18 (m, 2H), 6.80 (m, 2H).
Elementary analysis C
28H
20N
2O
2(438.61) calculated value: C80.75, H4.84, N6.73; Measured value: C80.41, H4.92, N6.57.
Embodiment 2
The preparation of luminous polypropylene fiber
Raw material: polypropylene 200g fluorescent chemicals 2g
Preparation method: above-mentioned raw materials is mixed the back carry out melt blending, extrude spinning with multifilament 400 melt spinning machines.Spinning speed 400m/min, 270 ℃ of spinning temperatures, 2.8 times of after-drawing multiples.
The result: a luminescent fibre stretching silk specification 68dtex/18f, intensity 3.83cN/dtex, maximum emission wavelength are 534nm.
Embodiment 3
The preparation of luminous polypropylene fiber
Raw material: polypropylene 200g fluorescent chemicals 4g
Preparation method: above-mentioned raw materials is mixed the back carry out melt blending, extrude spinning with multifilament 400 melt spinning machines.Spinning speed 400m/min, 270 ℃ of spinning temperatures, 2.8 times of after-drawing multiples.
The result: a luminescent fibre stretching silk specification 64dtex/18f, intensity 3.59cN/dtex, maximum emission wavelength are 534nm.
Claims (7)
1. method that adopts organic fluorescent compounds to prepare the fluorescence polypropylene fibre comprises:
(1) take by weighing 1～3g salicylide and derivative thereof and be dissolved in the absolute ethyl alcohol, water-bath is heated to 70～100 ℃, and slowly drips the ethanolic solution of 0.1～0.2g diamine compound, condensing reflux 1～3h; Leave standstill, get glassy yellow, orange red or red precipitate, filtering-depositing; And with filtering behind the ethyl alcohol recrystallization, oven dry gets organic fluorescent compounds; Wherein, described salicylaldehyde derivatives structure shown in (I), R wherein
1, R
2Be hydrogen atom, electron withdraw group or electron donating group, n
2Integer for 1-3
(2) 150～300g polypropylene and 2～5g fluorescent chemicals are mixed, carry out melt blending, extrude with multifilament 400 melt spinning machines, spinning, spinning speed 400m/min, 270 ℃ of spinning temperatures, 2.8 times of after-drawing multiples obtain the fluorescence radiation fiber.
2. employing organic fluorescent compounds according to claim 1 prepares the method for fluorescence polypropylene fibre, it is characterized in that: the concrete structure of described diamine compound is like (II) or (III), n
1Integer for 0-6.
3. employing organic fluorescent compounds according to claim 2 prepares the method for fluorescence polypropylene fibre, it is characterized in that: described diamine compound is the 85wt% hydrazine hydrate.
4. employing organic fluorescent compounds according to claim 1 prepares the method for fluorescence polypropylene fibre, it is characterized in that: described organic fluorescent compounds structure is shown in (IV):
Glassy yellow, orange or red solid, 76～400 ℃ of melting ranges, wherein, R is aromatic rings or aliphatic hydrocarbon, R
1, R
2Be hydrogen atom, electron withdraw group or electron donating group, n
1Be the integer of 0-10, n
2Integer for 1-3.
5. employing organic fluorescent compounds according to claim 4 prepares the method for fluorescence polypropylene fibre, it is characterized in that: described aromatic rings is that the structural formula of phenyl ring Ph is:
6. prepare the method for fluorescence polypropylene fibre according to claim 4 or 5 described employing organic fluorescent compounds, it is characterized in that: described R
1, R
2For H ,-NO
2Or-N-(C
2H
5)
2, n
1=0-6, n
2The structural formula of=1-2 is:
positive butanediamine two (3-diethylamino) salicylides that contract.
7. employing organic fluorescent compounds according to claim 1 prepares the method for fluorescence polypropylene fibre, it is characterized in that: described luminescent fibre carrier is a polypropylene; Used spinning process is a melt spinning, and described organic fluorescent compounds is said Schiff bases compound.
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| CN101619032B (en) * | 2009-08-04 | 2012-12-26 | 中国科学院上海微系统与信息技术研究所 | Schiff base compound and uses thereof |
| CN101864605A (en) * | 2010-06-09 | 2010-10-20 | 蚌埠市瑞进防伪材料科技有限公司 | Near-infrared absorption counterfeit fiber and preparation method thereof |
| CN103361753A (en) * | 2012-04-06 | 2013-10-23 | 莆田市华峰工贸有限公司 | Luminous fiber, luminous yarn and method for preparing luminous yarn |
| CN102816086A (en) * | 2012-07-30 | 2012-12-12 | 天津师范大学 | Salicylidenehydrazine receptor compound, preparation method and application thereof |
| CN102776592B (en) * | 2012-08-14 | 2014-04-02 | 青岛青禾人造草坪有限公司 | Artificial grass with fluorescence effect and preparation method of artificial grass |
| CN103113393A (en) * | 2013-03-07 | 2013-05-22 | 桂林理工大学 | Amino acid schiff base transition metal complex and application thereof |
| CN104610957B (en) * | 2015-01-28 | 2017-10-03 | 南通华纶化纤有限公司 | Europium luminous polyester fiber and preparation method thereof |
| CN108358814B (en) * | 2018-02-09 | 2020-05-22 | 许昌学院 | AIE fluorescent probe based on salicylhydrazone derivative and preparation method and application thereof |
| CN110845361B (en) * | 2018-07-24 | 2022-08-12 | 香港科技大学深圳研究院 | Compound based on excited state intramolecular proton transfer type and preparation method and application thereof |
| CN115821423A (en) * | 2022-12-06 | 2023-03-21 | 江南大学 | Polylactic acid fluorescent solar energy collection optical fiber and preparation method and application thereof |
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