CN108047492A - A kind of plastics of poly- 2,5- furandicarboxylic acids glycol ester nucleating agent and its rapid crystallization - Google Patents
A kind of plastics of poly- 2,5- furandicarboxylic acids glycol ester nucleating agent and its rapid crystallization Download PDFInfo
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- CN108047492A CN108047492A CN201711339338.XA CN201711339338A CN108047492A CN 108047492 A CN108047492 A CN 108047492A CN 201711339338 A CN201711339338 A CN 201711339338A CN 108047492 A CN108047492 A CN 108047492A
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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Abstract
The invention discloses a kind of application of different monooctyl ester of 2,5 furandicarboxylic acid in poly- 2,5 furandicarboxylic acid glycol ester as nucleating agent.The invention also discloses a kind of poly- the 2 of rapid crystallization, 5 furandicarboxylic acid glycol ester plastics, according to mass percent meter, including following components：Poly- 2,5 furandicarboxylic acid glycol ester 85~98%；The different monooctyl ester 2~15% of 2,5 furandicarboxylic acids.The invention also discloses poly- the 2 of a kind of rapid crystallization, the preparation method of 5 furandicarboxylic acid glycol ester plastics, by the different monooctyl ester of 2,5 furandicarboxylic acids and poly- 2, after 5 furandicarboxylic acid glycol esters premix uniformly according to mass percent, obtained after squeezing out tie rod by double screw extruder melt blending.Poly- 2,5 furandicarboxylic acid glycol ester plastics of the rapid crystallization of the present invention have faster crystalline rate and higher relative crystallinity, and injection molding cycle is short, and preparation method is simple, and production cost is low, suitable for industrialized production.
Description
Technical field
The present invention relates to polymeric material fields, and in particular to a kind of poly- 2,5-furandicarboxylic acid glycol ester nucleating agent and
The plastics of its rapid crystallization.
Background technology
Poly- 2,5-furandicarboxylic acid glycol ester has higher glass transition temperature, excellent oxygen, carbon dioxide
And the barrier property of water is widely used.But since the molecular symmetry of monomer 2,5-furandicarboxylic acid is relatively low, rigidity is strong,
And intermolecular dipole effect is greatly so that the movement of segment in crystallization process of poly- 2,5- furandicarboxylic acids glycol ester is subject to
It obstructs, crystalline rate is slow, and the processing and forming cycle is long, limits poly- 2,5-furandicarboxylic acid glycol ester answering in production and living
With.
The currently used method for accelerating crystalline rate is to add nucleating agent in the base.This method is simple and practicable, effect
Preferably, but the compatibility of general inorganic nucleator and matrix is poor, and agglomeration easily occurs.
The Chinese invention patent of 107118521 A of Publication No. CN discloses a kind of poly- furandicarboxylic acid glycol ester tree
Oil/fat composition considerably improves the crystalline rate of poly- furandicarboxylic acid glycol ester and opposite crystallization by adding in nucleating agent
Degree；Used nucleating agent is talcum powder, the double lauroyl of sodium carbonate, silica, isobide, sodium benzoate, N, N '-ethylene
One or more of ionomer of amine and ethylene-methyl methacrylate.
The content of the invention
The present invention provides a kind of different monooctyl ester of 2,5- furandicarboxylic acids conducts in poly- 2,5- furandicarboxylic acids glycol ester
The application of nucleating agent.Nucleating agent is made using the different monooctyl ester of 2,5-furandicarboxylic acid, makes the knot of poly- 2,5-furandicarboxylic acid glycol ester
Brilliant rate and relative crystallinity substantially increase.
A kind of application of different monooctyl ester of 2,5-furandicarboxylic acid in poly- 2,5-furandicarboxylic acid glycol ester as nucleating agent,
The different monooctyl ester of the 2,5-furandicarboxylic acid has structure shown below formula：
The different monooctyl ester of 2,5-furandicarboxylic acid can promote the movement that between polymer macromolecule or chain is intersegmental, reduce between molecule
Frictional force, accelerate crystalline rate；And the different monooctyl ester of 2,5- furandicarboxylic acids has with poly- 2,5- furandicarboxylic acids glycol ester
Good compatibility, overcomes inorganic nucleator and matrix compatibility is poor, the shortcomings that easily reunion.
The different monooctyl ester of the 2,5-furandicarboxylic acid may be employed conventional method and be prepared, and can also use following step
Suddenly：
(1) isooctanol, 2,5-furandicarboxylic acid and catalyst are mixed, is heated in protective atmosphere, react 3~5h；
(2) excessive isooctanol is evaporated in heating, stops reaction after 3~4h, obtains crude product；
(3) crude product is post-processed, obtains the different monooctyl ester of 2,5-furandicarboxylic acid.
Alcohol is suitably excessive, is conducive to the abundant progress of esterification.
Preferably, the molar ratio of the isooctanol and 2,5-furandicarboxylic acid described in step (1) is 2.5~3:1.
Preferably, the catalyst described in step (1) is p-methyl benzenesulfonic acid, reaction solution is soluble in, belongs to homogeneous catalysis,
It is higher to the catalytic efficiency of reaction.
The temperature of reaction described in step (1) is 160~180 DEG C.
Reaction temperature is higher in step (1), need to be carried out in protective atmosphere, and the side reactions such as oxidation otherwise can occur, cause
Impurity increases in system, and product quality declines.
Protective atmosphere described in step (1) is protective gas well known to those skilled in the art,
Preferably, protective atmosphere is nitrogen, helium or argon gas.
Preferably, the temperature of the heating described in step (2) is 185~195 DEG C, the temperature range is higher than isooctanol
Boiling point less than the boiling point of product, can preferably remove unreacted isooctanol simultaneously.
Post processing described in step (3) is：Add in anhydrous MgSO4Moisture is removed, filters and removes MgSO4Solid, Ran Houyong
Saturation Na2CO3Washing removes catalyst.
The preparation method of the different monooctyl ester of 2,5-furandicarboxylic acid of the present invention is simple, and controllability is strong.
The present invention also provides a kind of poly- 2,5-furandicarboxylic acid glycol ester plastics of rapid crystallization, according to quality percentage
Than meter, including following components：
Poly- 2,5- furandicarboxylic acids glycol ester 85~98%；
The different monooctyl ester 2~15% of 2,5- furandicarboxylic acids.
When the additive amount of the different monooctyl ester of 2,5-furandicarboxylic acid is 2~10%, to poly- 2,5-furandicarboxylic acid glycol ester
Crystallization facilitating effect is more notable.
Preferably, a kind of poly- 2,5-furandicarboxylic acid glycol ester plastics of rapid crystallization, according to mass percent meter,
Including following components：
Poly- 2,5- furandicarboxylic acids glycol ester 90~98%；
The different monooctyl ester 2~10% of 2,5- furandicarboxylic acids.
The present invention also provides a kind of preparation method of the poly- 2,5-furandicarboxylic acid glycol ester plastics of rapid crystallization, bags
Include following steps：
By the dry different monooctyl ester of 2,5- furandicarboxylic acids and poly- 2,5- furandicarboxylic acids glycol ester according to mass percent
Premix uniformly obtains mixed material, then obtains mixed material fast by squeezing out tie rod after double screw extruder melt blending
The poly- 2,5- furandicarboxylic acids glycol ester plastics of speed crystallization.
The temperature of the melt blending is 210~230 DEG C.
The time of the melt blending is 4~7min.
The screw speed of the double screw extruder is 80~100r/min.
The screw slenderness ratio of the double screw extruder is 35~45:1.
The present invention rapid crystallization poly- 2,5- furandicarboxylic acids glycol ester plastics have faster crystalline rate and compared with
High relative crystallinity, injection molding cycle is short, and preparation method is simple, and production cost is low, suitable for industrialized production.
Description of the drawings
Fig. 1 is the hydrogen spectrogram of the different monooctyl ester of 2,5- furandicarboxylic acids prepared by embodiment 1.
Fig. 2 is the carbon spectrogram of the different monooctyl ester of 2,5- furandicarboxylic acids prepared by embodiment 1.
Fig. 3 (a) is the isothermal crystal differential scanning calorimetry of poly- 2,5- furandicarboxylic acids glycol ester at different temperatures
(DSC) figure.
Fig. 3 (b) is poly- 2,5- furandicarboxylic acids glycol ester/different monooctyl ester of 2,5- furandicarboxylic acids prepared by embodiment 2
Isothermal crystal differential scanning calorimetry (DSC) figure of (2wt%) plastics at different temperatures.
Fig. 3 (c) is the second melting heating curve of poly- 2,5- furandicarboxylic acids glycol ester.
Fig. 3 (d) is poly- 2,5- furandicarboxylic acids glycol ester/different monooctyl ester of 2,5- furandicarboxylic acids prepared by embodiment 2
The second melting heating curve of (2wt%) plastics.
Specific embodiment
The present invention is described in further detail with reference to specific embodiment, these embodiments are intended to be convenient for the present invention
Understanding rather than limit the scope of the invention in any way.
Embodiment 1
39.0g (0.3mol) isooctanol, 15.6g (0.1mol) 2,5- furandicarboxylic acids and 0.8g p-methyl benzenesulfonic acid is taken to be placed in
In the three neck round bottom flask of 250mL, in N2170 DEG C of reflux 4h are warming up under atmosphere, until the water level in water knockout drum no longer rises
Until；Reaction temperature is risen to 190 DEG C again, evaporates excessive isooctanol, the steam flavescence under being condensed in reaction bottle wall is
Only, reaction is stopped；Anhydrous MgSO is added in into obtained crude product4Moisture is removed, and filters and removes MgSO4Solid particle, then
With saturation Na2CO3Washing removes p-methyl benzenesulfonic acid, obtains the different monooctyl ester of product 2,5-furandicarboxylic acid.
The different monooctyl ester of 2,5-furandicarboxylic acid obtained is yellow liquid, and the results are shown in Figure 1 for hydrogen stave sign：1H-NMR
(400MHz,d6-DMSO)δ：7.38 (s, 2H), 4.12-4.24 (d, 4H), 1.62-1.68 (m, 2H), 1.20-1.40 (m, 8H),
0.82-0.90 (t, 12H)；
The results are shown in Figure 2 for carbon stave sign：13C-NMR(400MHz,DMSO)δ：157.86 (C3), 146.65 (C2),
119.27 (C1), 67.58 (C4), 38.65 (C5), 30.23 (C6), 28.77 (C7), 23.69 (C10), 22.83 (C8), 14.22
(C9),11.18(C11)。
From Fig. 1 and 2, the different monooctyl ester of 2,5-furandicarboxylic acid is successfully synthesized, there is structure shown below formula：
Embodiment 2
The different monooctyl ester of 2,5- furandicarboxylic acids and poly- furandicarboxylic acid glycol ester are put into 80 DEG C of vacuum drying oven respectively
6h is dried, then takes the poly- 2,5-furandicarboxylic acid glycol esters of 12g and the different monooctyl ester of 0.25g 2,5-furandicarboxylic acid, after mixing
It adds mixture in double screw extruder, melt blending temperature setting is 220 DEG C, and rotating speed is arranged to 80r/min, mixing
It is squeezed out after 5min, the poly- 2,5-furandicarboxylic acid glycol ester/different monooctyl ester of 2,5-furandicarboxylic acid (2wt%) plastics is made, write a Chinese character in simplified form
For PEF/DEHF (2wt%).
Embodiment 3
The different monooctyl ester of 2,5- furandicarboxylic acids and poly- furandicarboxylic acid glycol ester are put into 80 DEG C of vacuum drying oven respectively
6h is dried, then takes the poly- 2,5-furandicarboxylic acid glycol esters of 12g and the different monooctyl ester of 0.63g 2,5-furandicarboxylic acid, after mixing
It adds mixture in double screw extruder, melt blending temperature setting is 220 DEG C, and rotating speed is arranged to 80r/min, mixing
It is squeezed out after 5min, the poly- 2,5-furandicarboxylic acid glycol ester/different monooctyl ester of 2,5-furandicarboxylic acid (5wt%) plastics is made, write a Chinese character in simplified form
For PEF/DEHF (5wt%).
Embodiment 4
The different monooctyl ester of 2,5- furandicarboxylic acids and poly- furandicarboxylic acid glycol ester are put into 80 DEG C of vacuum drying oven respectively
6h is dried, then takes the poly- 2,5-furandicarboxylic acid glycol esters of 12g and the different monooctyl ester of 1.33g 2,5-furandicarboxylic acid, after mixing
It adds mixture in double screw extruder, melt blending temperature setting is 220 DEG C, and rotating speed is arranged to 80r/min, mixing
It is squeezed out after 5min, the poly- 2,5-furandicarboxylic acid glycol ester/different monooctyl ester of 2,5-furandicarboxylic acid (10wt%) plastics is made, write a Chinese character in simplified form
For PEF/DEHF (10wt%).
Embodiment 5
The different monooctyl ester of 2,5- furandicarboxylic acids and poly- furandicarboxylic acid glycol ester are put into 80 DEG C of vacuum drying oven respectively
6h is dried, then takes the poly- 2,5-furandicarboxylic acid glycol esters of 12g and the different monooctyl ester of 2.12g 2,5-furandicarboxylic acid, after mixing
It adds mixture in double screw extruder, melt blending temperature setting is 220 DEG C, and rotating speed is arranged to 80r/min, mixing
It is squeezed out after 5min, the poly- 2,5-furandicarboxylic acid glycol ester/different monooctyl ester of 2,5-furandicarboxylic acid (15wt%) plastics is made, write a Chinese character in simplified form
For PEF/DEHF (15wt%).
Isothermal crystal is tested
It is inferior at 150,160,165,170,175,180 DEG C respectively to weigh the poly- 2,5- furandicarboxylic acids glycol esters of 7~9mg
Temperature crystallization 90min；The poly- 2,5- furandicarboxylic acids glycol ester/2,5- furandicarboxylic acids for weighing the preparation of 7~9mg embodiments 2 are different
Monooctyl ester plastics, the isothermal crystal 30min at 150,160,165,170,175,180 DEG C, is surveyed by differential scanning calorimeter respectively
Try the isothermal crystal performance of the two.
It is real shown in the isothermal crystal DSC results such as Fig. 3 (a) of poly- 2,5-furandicarboxylic acid glycol ester at different temperatures
The poly- 2,5- furandicarboxylic acids glycol ester/different monooctyl ester of 2,5- furandicarboxylic acids (2wt%) plastics of the preparation of example 2 are applied in different temperatures
Under isothermal crystal DSC figures as shown in Fig. 3 (b)；Comparison diagram 3 (a) understands the poly- 2,5- furans two of the preparation of embodiment 2 with Fig. 3 (b)
The peak crystallization narrowed width of the isothermal crystal curve of the formic acid glycol ester/different monooctyl ester of 2,5-furandicarboxylic acid (2wt%) plastics, says
Bright crystallization time is shorter.
Shown in second melting heating curve such as Fig. 3 (c) of poly- 2,5-furandicarboxylic acid glycol ester, prepared by embodiment 2
The second melting heating curve of the poly- 2,5- furandicarboxylic acids glycol ester/different monooctyl ester of 2,5- furandicarboxylic acids (2wt%) plastics is such as
Shown in Fig. 3 (d)；Comparison diagram 3 (c) is understood with Fig. 3 (d)：Poly- 2,5- furandicarboxylic acids glycol ester and poly- the 2 of the preparation of embodiment 2,
The trend of the second melting curve of the 5- furandicarboxylic acids glycol ester/different monooctyl ester of 2,5-furandicarboxylic acid (2wt%) plastics is consistent,
The melting process of matrix can't be influenced by illustrating the addition of the different monooctyl ester of 2,5- furandicarboxylic acids.
Poly- 2,5- furandicarboxylic acids glycol ester and poly- 2,5- furans prepared by embodiment 2 are drawn by isothermal crystal test
Naphthalate/melting enthalpy Δ of 2,5- furandicarboxylic acids different monooctyl ester (2wt%) plastics at a temperature of different isothermal crystals
Hm；Avrami index n, crystallization rate constant k, flexible chain t are calculated using Avrami formula1/2With relative crystallinity Xc,WhereinM is the mass percent of nucleating agent.Poly- 2,5- furandicarboxylic acids ethylene glycol
The knot of the poly- 2,5- furandicarboxylic acids glycol ester/different monooctyl ester of 2,5- furandicarboxylic acids (2wt%) plastics prepared by ester and embodiment 2
Brilliant performance parameter is shown in Table 1.
The crystal property parameter of PEF/DEHF (2wt%) prepared by table 1PEF and embodiment 2
By the flexible chain t in table 11/2With relative crystallinity XcIt can draw, the different monooctyl ester of 2,5-furandicarboxylic acid adds
Enter the crystalline rate and relative crystallinity for significantly improving poly- 2,5- furandicarboxylic acids glycol ester；At 165 DEG C prepared by embodiment 2
The poly- 2,5- furandicarboxylic acids glycol ester/different monooctyl ester of 2,5- furandicarboxylic acids (2wt%) plastics flexible chain t1/2Shorten
To 8.41min, and relative crystallinity increases.
Claims (10)
1. a kind of application of different monooctyl ester of 2,5-furandicarboxylic acid in poly- 2,5-furandicarboxylic acid glycol ester as nucleating agent, institute
The different monooctyl ester of 2,5- furandicarboxylic acids stated has structure shown below formula：
2. the different monooctyl ester of 2,5- furandicarboxylic acids conduct in poly- 2,5- furandicarboxylic acids glycol ester according to claim 1
The application of nucleating agent, which is characterized in that the preparation method of the different monooctyl ester of the 2,5-furandicarboxylic acid comprises the following steps：
(1) isooctanol, 2,5-furandicarboxylic acid and catalyst are mixed, is heated in protective atmosphere, react 3~5h；
(2) excessive isooctanol is evaporated in heating, stops reaction after 3~4h, obtains crude product；
(3) crude product is post-processed, obtains the different monooctyl ester of 2,5-furandicarboxylic acid.
3. the different monooctyl ester of 2,5- furandicarboxylic acids conduct in poly- 2,5- furandicarboxylic acids glycol ester according to claim 2
The application of nucleating agent, which is characterized in that the molar ratio of isooctanol and 2,5-furandicarboxylic acid described in step (1) for 2.5~
3:1。
4. the different monooctyl ester of 2,5- furandicarboxylic acids conduct in poly- 2,5- furandicarboxylic acids glycol ester according to claim 2
The application of nucleating agent, which is characterized in that the temperature of the reaction described in step (1) is 160~180 DEG C.
5. the different monooctyl ester of 2,5- furandicarboxylic acids conduct in poly- 2,5- furandicarboxylic acids glycol ester according to claim 2
The application of nucleating agent, which is characterized in that the temperature of the heating described in step (2) is 185~195 DEG C.
6. a kind of poly- 2,5-furandicarboxylic acid glycol ester plastics of rapid crystallization, which is characterized in that according to mass percent meter,
Including following components：
Poly- 2,5- furandicarboxylic acids glycol ester 85~98%；
The different monooctyl ester 2~15% of 2,5- furandicarboxylic acids.
7. the preparation method of the poly- 2,5-furandicarboxylic acid glycol ester plastics of rapid crystallization according to claim 6,
It is characterized in that, comprises the following steps：
The dry different monooctyl ester of 2,5- furandicarboxylic acids and poly- 2,5- furandicarboxylic acids glycol ester are premixed according to mass percent
Mixed material uniformly is obtained, is then quickly tied mixed material by squeezing out tie rod after double screw extruder melt blending
Brilliant poly- 2,5- furandicarboxylic acids glycol ester plastics.
8. the preparation method of the poly- 2,5-furandicarboxylic acid glycol ester plastics of rapid crystallization according to claim 7,
It is characterized in that, the temperature of the melt blending is 210~230 DEG C.
9. the preparation method of the poly- 2,5-furandicarboxylic acid glycol ester plastics of rapid crystallization according to claim 7,
It is characterized in that, the time of the melt blending is 4~7min.
10. the preparation method of the poly- 2,5-furandicarboxylic acid glycol ester plastics of rapid crystallization according to claim 7,
It is characterized in that, the screw slenderness ratio of the double screw extruder is 35~45:1, the screw rod of the double screw extruder turns
Speed is 80~100r/min.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115028973A (en) * | 2021-03-03 | 2022-09-09 | 中国科学院宁波材料技术与工程研究所 | Bio-based additive for promoting rapid crystallization of polylactic acid and application thereof |
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| CN115028973A (en) * | 2021-03-03 | 2022-09-09 | 中国科学院宁波材料技术与工程研究所 | Bio-based additive for promoting rapid crystallization of polylactic acid and application thereof |
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