CN104151538A - Preparation method and application of hydroxyl-terminated perylene imide hyperbranched polyester - Google Patents
Preparation method and application of hydroxyl-terminated perylene imide hyperbranched polyester Download PDFInfo
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- CN104151538A CN104151538A CN201410388706.XA CN201410388706A CN104151538A CN 104151538 A CN104151538 A CN 104151538A CN 201410388706 A CN201410388706 A CN 201410388706A CN 104151538 A CN104151538 A CN 104151538A
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Abstract
The invention discloses a preparation method and application of hydroxyl-terminated perylene imide hyperbranched polyester. The preparation method comprises the following steps: adding perylene anhydride and ethanol into a three-mouth flask, dropwise adding ethanol amine while stirring, heating for reaction for 8-10 hours, precipitating by distilled water, filtering, washing filter residues by a KOH aqueous solution, and drying in a vacuum drying box to prepare an intermediate product; dissolving the intermediate product in acetone, adding an organic tin catalyst, heating for reaction for 15 minutes, dropwise adding an acetone solution in which methylbenzene-2,4-diisocyanate is dissolved, and reacting for 1-3 hours to prepare an intermediate system; dissolving hyperbranched polyester H20 in acetone, dropwise adding into the intermediate system, reacting for 5-6 hours, pouring a reaction product into the distilled water for precipitating, filtering, and drying in vacuum to obtain a purple red product, namely the hydroxyl-terminated perylene imide hyperbranched polyester. The hydroxyl-terminated perylene imide hyperbranched polyester prepared by the method is applied to toughening modification of thermoplastic and thermosetting resin, and the mechanical property and heat property of a material can be remarkably improved.
Description
Technical field
The invention belongs to polymer modification technical field, particularly relate to a kind of preparation method and application thereof of Duan Qiang Ji perylene diimide hyper-branched polyester.
Background technology
The planar conjugate structure of perylene diimide and derivative Han You perylene acid anhydride parent thereof, has large conjugation
πelectron system, intermolecular existence is stronger
π-πinteract.Yin perylene diimide analog derivative is electron deficiency system, therefore it is as good electron acceptor(EA), easily electron gain, has very high electron affinity, is a kind of typical N-shaped organic semiconductor material.
You Yu perylene diimide derivative has common phenyl ring two dimensional structure, and its lattice energy is very large, and rigidity is high, has good thermostability, and can effectively improve the thermostability of polymer matrix composite.Simultaneously ， perylene diimide derivative is as a kind of special condensed-nuclei aromatics, and the bay position of Tong Guo perylene diimide molecule or imide position are introduced different functional groups and carried out chemically modified, can well coordinate various non covalent bond reactive forces, comprise hydrogen bond,
π-πinteraction, Van der Waals force etc., can reduce its rigidity as introduced longer segment, thereby reach the object of improving its performance.Since Friedlander in 1913 synthesizes perylene diimides (PDI), due to its outstanding dyeing behavior, the good feature such as light stability and unreactiveness, be widely used in the field such as dyestuff and coating always.
Epoxy resin (EP) is as a kind of thermosetting resin, there is the processing of being easy to, storage, the advantage such as the flexible and changeable and cost of formulating of recipe is cheap, the premium properties such as that its cured article has is wear-resisting, resistance to chemical attack, electrical isolation, gluing power are strong and shrinking percentage is little, being widely used in the fields such as tackiness agent, coating, electronic apparatus, structured material, is one of most widely used matrix resin in polymer matrix composite.But because the cured article cross-linking density of epoxy resin is high, internal stress is large, therefore there is the shortcomings such as matter is crisp, impact resistance is poor, thermotolerance is low, is difficult to meet the requirement of engineering, limit its application in high-strength, high tenacity and the high field such as heat-resisting.For addressing these problems, Chinese scholars has been attempted the multiple method to Toughening Epoxy Resin, the method such as such as rubber elastomer is toughness reinforcing, TLCP is toughness reinforcing, interpenetrating net polymer is toughness reinforcing, Rigid Particles Toughened, Core-Shell Polymer Particles are toughness reinforcing.These method of modifying, can effectively improve the toughness of epoxy resin cured product, but have reduced its thermotolerance, hardness and modulus.
In recent years, obtained comparatively satisfied result with hyperbranched polymer Toughening Modification of Epoxy, it can not only improve the toughness of epoxy resin, does not reduce the performances such as its thermotolerance, modulus simultaneously.5 wt% study on hyperbranched polymer modified epoxy resins for L.Boogh etc., its critical energy release rate G
iCfor 720J/m
2, increased by 6 times than pure epoxy resin, fracture toughness property K
iCfrom 0.63MPa
.m
1/2be increased to 1.54MPa
.m
1/2, its hardness and second-order transition temperature do not decline.Sun will has etc. has reported " a kind of preparation method who contains the low branched polyester liquid crystal of xenyl " (ZL201110049224.8).Utilize this low branched polyester liquid crystal modified epoxy, research shows that a small amount of hyper-branched polyester liquid crystal can improve toughness, modulus and the thermotolerance of epoxy resin significantly.Meanwhile, also shown that hyperbranched polymer can effectively improve mechanical property and the thermal characteristics of matrix material.
In above-mentioned research, hyperbranched polymer used does not all relate to the dissaving structure taking aromatic hydrocarbon as core, and Er is taking perylene acid anhydride, hyper-branched polyester H20 as main raw material, the superbrnaching end-hydroxy polyester of synthesizing new for Toughening Modification of Epoxy.
Of the present invention Jiang Yi perylene acid anhydride, thanomin, Toluene-2,4-diisocyanate, 4-vulcabond (TDI) and hyper-branched polyester (H20) are main raw material, the Duan Qiang Ji perylene diimide hyper-branched polyester of synthesizing new.At present there are no bibliographical information.
Summary of the invention
The object of this invention is to provide a kind of preparation method and application thereof of Duan Qiang Ji perylene diimide hyper-branched polyester.
The concrete steps of preparation Duan Qiang Ji perylene diimide hyper-branched polyester are:
(1) in 250ml there-necked flask, add 1.5 ~ 5.0g perylene acid anhydride and 80 ~ 150ml ethanol, stir the thanomin of the lower 1.5 ~ 5ml of dropping, then be warming up to 75 ~ 90 DEG C, react and precipitate with distilled water after 8 ~ 10 hours, filter, the KOH solution washing of 1 mol/L three times for filter residue, removes Wei reaction perylene acid anhydride and monosubstituted thing, is then placed in the dry intermediate product that makes of vacuum drying oven.
(2) intermediate product 0.2 ~ 1.0g step (1) being made is dissolved in the acetone of 5 ~ 10ml, add 0.1 ~ 0.5g organotin catalysts, be warming up to 55 ~ 70 DEG C of reactions after 15 minutes, slowly drip and be dissolved with 0.3 ~ 1.5g Toluene-2,4-diisocyanate, the acetone soln of 4-vulcabond, system in the middle of isothermal reaction made after 1 ~ 3 hour.
(3) 1.5 ~ 6.0g hyper-branched polyester H20 is dissolved in 20 ~ 50ml acetone, then be slowly added drop-wise in the middle system that step (2) makes, at 55 ~ 60 DEG C, react after 5 ~ 6 hours, reactant is poured in distilled water and precipitated, filter, after vacuum-drying, obtain red-purple product and be Duan Qiang Ji perylene diimide hyper-branched polyester.
Described organotin catalysts is one or more in two lauric acid diisobutyl tin, stannous octoate and dibutyltin diacetate.
Duan Qiang Ji perylene diimide hyper-branched polyester prepared by the present invention is applied to the toughening modifying of thermoplasticity and thermosetting resin.
The present invention has the following advantages:
(1) synthesis material source is wide, cheap, pollutes little.
(2) processing ease, synthetic and modified technique is simple, be expected to drop into suitability for industrialized production.
(3) Duan Qiang Ji perylene diimide hyper-branched polyester and the matrix resin prepared have excellent compatibility, each analog thermoplastic and thermosetting resin are had to obvious toughening effect, can significantly improve mechanical property and the thermal characteristics of material, especially in the time of modified epoxy, its terminal hydroxy group also participates in curing reaction, plays the effect of curing catalyst.
Embodiment
embodiment 1:
The main raw material that the present embodiment is prepared Duan Qiang Ji perylene diimide hyper-branched polyester is: perylene acid anhydride (analytical pure), acetone (analytical pure), ethanol (analytical pure), thanomin (analytical pure), Toluene-2,4-diisocyanate, 4-vulcabond (TDI, analytical pure), hyper-branched polyester (H20, technical grade), epoxy resin E-44 (technical grade), 4,4 '-diaminodiphenylsulfone(DDS) (DDS, technical grade), dibutyl tin laurate (analytical pure).
Concrete steps are:
(1) in 250ml there-necked flask, add 1.5g perylene acid anhydride and 80ml ethanol, stir the thanomin of the lower 1.5ml of dropping, then be warming up to 75 DEG C, react and precipitate with distilled water after 8 hours, filter, the KOH solution washing of 1 mol/L three times for filter residue, removes Wei reaction perylene acid anhydride and monosubstituted thing, is then placed in the dry intermediate product that makes of vacuum drying oven.
(2) intermediate product 0.2g step (1) being made is dissolved in the acetone of 5ml, add 0.1g dibutyl tin laurate to make catalyzer, be warming up to 55 DEG C of reactions after 15 minutes, slowly drip and be dissolved with 0.3g Toluene-2,4-diisocyanate, the acetone soln of 4-vulcabond, system in the middle of isothermal reaction made after 1 hour.
(3) 1.5g hyper-branched polyester H20 is dissolved in 20ml acetone, then be slowly added drop-wise in the middle system that step (2) makes, at 55 DEG C, react after 5 hours, reactant is poured in distilled water and precipitated, filter, after vacuum-drying, obtain red-purple product and be Duan Qiang Ji perylene diimide hyper-branched polyester.
Duan Qiang Ji perylene diimide hyper-branched polyester prepared by the present embodiment is applied to Toughening Epoxy Resin:
Getting Duan Qiang Ji perylene diimide hyper-branched polyester prepared by 0.13g the present embodiment joins in 26.0g epoxy resin-base, decompression is bled, add again 7.8g DDS solidifying agent, after dissolving completely, pours into by solidifying agent in the steel die that scribbles estersil, in 140 DEG C/2 hours+160 DEG C/2 hours+180 DEG C/2 hours lower curing moldings, make Duan Qiang Ji perylene diimide hyper-branched polyester modified epoxy resin composite.Epoxy resin after this Duan Qiang Ji perylene diimide hyper-branched polyester (0.5wt% that consumption is epoxy resin) modification, its shock strength is by 26.25 kJ/m of pure epoxy resin
2bring up to 32.92 kJ/m
2, improving 25.4%, tensile strength improves 34%, and flexural strength increases by 62%, and thermolysis starting temperature has improved 28 DEG C.
embodiment 2:
(1) in 250ml there-necked flask, add 3.0g perylene acid anhydride and 120ml ethanol, stir the thanomin of the lower 3ml of dropping, then be warming up to 80 DEG C, react and precipitate with distilled water after 9 hours, filter, the KOH solution washing of 1 mol/L three times for filter residue, removes Wei reaction perylene acid anhydride and monosubstituted thing, is then placed in the dry intermediate product that makes of vacuum drying oven.
(2) intermediate product 0.5g step (1) being made is dissolved in the acetone of 8ml, add 0.2g dibutyl tin laurate to make catalyzer, be warming up to 60 DEG C of reactions after 15 minutes, slowly drip and be dissolved with 0.7g Toluene-2,4-diisocyanate, the acetone soln of 4-vulcabond, system in the middle of isothermal reaction made after 2 hours.
(3) 3.7g hyper-branched polyester H20 is dissolved in 30ml acetone, then be slowly added drop-wise in the middle system that step (2) makes, at 60 DEG C, react after 6 hours, reactant is poured in distilled water and precipitated, filter, after vacuum-drying, obtain red-purple product and be Duan Qiang Ji perylene diimide hyper-branched polyester.
Duan Qiang Ji perylene diimide hyper-branched polyester prepared by the present embodiment is applied to Toughening Epoxy Resin:
Getting Duan Qiang Ji perylene diimide hyper-branched polyester prepared by the present embodiment of 0.39g joins in 26.0g epoxy resin-base, decompression is bled, add again 7.8g DDS solidifying agent, after dissolving completely, pours into by solidifying agent in the steel die that scribbles estersil, in 140 DEG C/2 hours+160 DEG C/2 hours+180 DEG C/2 hours lower curing moldings, make Duan Qiang Ji perylene diimide hyper-branched polyester modified epoxy resin composite.Epoxy resin after this Duan Qiang Ji perylene diimide hyper-branched polyester (1.5 wt% that consumption is epoxy resin) modification, its shock strength is by 26.25 kJ/m of pure epoxy resin
2bring up to 47.6 kJ/m
2, improving 81%, tensile strength improves 62%, and flexural strength increases by 68%, and thermolysis starting temperature has improved 27 DEG C.
embodiment 3:
(1) in 250ml there-necked flask, add 5.0g perylene acid anhydride and 150ml ethanol, stir the thanomin of the lower 5ml of dropping, then be warming up to 85 DEG C, react and precipitate with distilled water after 10 hours, filter, the KOH solution washing of 1 mol/L three times for filter residue, removes Wei reaction perylene acid anhydride and monosubstituted thing, is then placed in the dry intermediate product that makes of vacuum drying oven.
(2) intermediate product 1.0g step (1) being made is dissolved in the acetone of 10ml, add 0.3g dibutyl tin laurate to make catalyzer, be warming up to 65 DEG C of reactions after 15 minutes, slowly drip and be dissolved with 1.5g Toluene-2,4-diisocyanate, the acetone soln of 4-vulcabond, system in the middle of isothermal reaction made after 3 hours.
(3) 5.3g hyper-branched polyester H20 is dissolved in 40ml acetone, then be slowly added drop-wise in the middle system that step (2) makes, at 60 DEG C, react after 6 hours, reactant is poured in distilled water and precipitated, filter, after vacuum-drying, obtain red-purple product and be Duan Qiang Ji perylene diimide hyper-branched polyester.
Duan Qiang Ji perylene diimide hyper-branched polyester prepared by the present embodiment is applied to Toughening Epoxy Resin:
Getting Duan Qiang Ji perylene diimide hyper-branched polyester prepared by 0.52g the present embodiment adds in 26.0 g epoxy resin-bases, decompression is bled, add again 7.8g DDS solidifying agent, after dissolving completely, pours into by solidifying agent in the steel die that scribbles estersil, in 140 DEG C/2 hours+160 DEG C/2 hours+180 DEG C/2 hours lower curing moldings, make Duan Qiang Ji perylene diimide hyper-branched polyester modified epoxy resin composite.Epoxy resin after this Duan Qiang Ji perylene diimide hyper-branched polyester (2 wt% that consumption is epoxy resin) modification, its shock strength is by the 26.25kJ/m of pure epoxy resin
2bring up to 37.24 kJ/m
2, improving 42%, tensile strength improves 61%, and flexural strength increases by 42%, and thermolysis starting temperature has improved 23 DEG C.
Claims (2)
1. hold a preparation method for hydroxyl base perylene diimide hyper-branched polyester, it is characterized in that concrete steps are:
(1) in 250ml there-necked flask, add 1.5 ~ 5.0g perylene acid anhydride and 80 ~ 150ml ethanol, stir the thanomin of the lower 1.5 ~ 5ml of dropping, then be warming up to 75 ~ 90 DEG C, react and precipitate with distilled water after 8 ~ 10 hours, filter, the KOH solution washing of 1 mol/L three times for filter residue, removes Wei reaction perylene acid anhydride and monosubstituted thing, is then placed in the dry intermediate product that makes of vacuum drying oven;
(2) intermediate product 0.2 ~ 1.0g step (1) being made is dissolved in the acetone of 5 ~ 10ml, add 0.1 ~ 0.5g organotin catalysts, be warming up to 55 ~ 70 DEG C of reactions after 15 minutes, slowly drip and be dissolved with 0.3 ~ 1.5g Toluene-2,4-diisocyanate, the acetone soln of 4-vulcabond, system in the middle of isothermal reaction made after 1 ~ 3 hour;
(3) 1.5 ~ 6.0g hyper-branched polyester H20 is dissolved in 20 ~ 50ml acetone, then be slowly added drop-wise in the middle system that step (2) makes, at 55 ~ 60 DEG C, react after 5 ~ 6 hours, reactant is poured in distilled water and precipitated, filter, after vacuum-drying, obtain red-purple product and be Duan Qiang Ji perylene diimide hyper-branched polyester;
Described organotin catalysts is one or more in two lauric acid diisobutyl tin, stannous octoate and dibutyltin diacetate.
2. the application of the Duan Qiang Ji perylene diimide hyper-branched polyester that preparation method according to claim 1 makes, is characterized in that this Duan Qiang Ji perylene diimide hyper-branched polyester is applied to the toughening modifying of thermoplasticity and thermosetting resin.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107337615A (en) * | 2016-08-09 | 2017-11-10 | 万华化学集团股份有限公司 | A kind of preparation method of isocyanates |
| CN109880060A (en) * | 2019-02-01 | 2019-06-14 | 安徽建筑大学 | A kind of dendroid water polyurethane base high molecular dye and preparation method |
| CN110724250A (en) * | 2019-09-30 | 2020-01-24 | 浙江恒澜科技有限公司 | Preparation method and application of aromatic alcohol modified polyester chip |
| CN110965362A (en) * | 2019-12-21 | 2020-04-07 | 苏州大学 | Branched-chain polyurethane thickener and preparation method thereof |
| CN112029338A (en) * | 2020-08-04 | 2020-12-04 | 无锡市盛意合成材料有限公司 | Preparation method of environment-friendly universal adhesion promoter |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107337615A (en) * | 2016-08-09 | 2017-11-10 | 万华化学集团股份有限公司 | A kind of preparation method of isocyanates |
| CN107337615B (en) * | 2016-08-09 | 2019-04-23 | 万华化学集团股份有限公司 | A kind of preparation method of isocyanates |
| CN109880060A (en) * | 2019-02-01 | 2019-06-14 | 安徽建筑大学 | A kind of dendroid water polyurethane base high molecular dye and preparation method |
| CN109880060B (en) * | 2019-02-01 | 2021-08-27 | 浙江材华科技有限公司 | Dendritic waterborne polyurethane-based high-molecular dye and preparation method thereof |
| CN110724250A (en) * | 2019-09-30 | 2020-01-24 | 浙江恒澜科技有限公司 | Preparation method and application of aromatic alcohol modified polyester chip |
| CN110965362A (en) * | 2019-12-21 | 2020-04-07 | 苏州大学 | Branched-chain polyurethane thickener and preparation method thereof |
| CN112029338A (en) * | 2020-08-04 | 2020-12-04 | 无锡市盛意合成材料有限公司 | Preparation method of environment-friendly universal adhesion promoter |
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|---|---|
| CN104151538B (en) | 2016-05-18 |
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Denomination of invention: Preparation and application of a hydroxyl terminated perylene imide hyperbranched polyester Effective date of registration: 20230420 Granted publication date: 20160518 Pledgee: Shaoxing Branch of Zhejiang Tailong Commercial Bank Co.,Ltd. Pledgor: Shaoxing Guenot SuperLing Lubrication Material Co.,Ltd. Registration number: Y2023980038605 |
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