CN104059395B - The preparation method of Yi Zhong perylene diimide urethane liquid crystal non-covalent modification Graphene - Google Patents
The preparation method of Yi Zhong perylene diimide urethane liquid crystal non-covalent modification Graphene Download PDFInfo
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Abstract
The invention discloses the preparation method of Yi Zhong perylene diimide urethane liquid crystal non-covalent modification Graphene.Join in N-Methyl pyrrolidone by perylene acid anhydride and zinc acetate, stir and be warming up to 150 ~ 160 DEG C, add diglycolamine, react 12 hours, pour precipitating discharging in dehydrated alcohol into, filter, vacuum-drying must hold hydroxyl base perylene diimide; Get Duan Qiang Ji perylene diimide and be dissolved in DMF, add hexamethylene diisocyanate and catalyzer, at N
2be warming up to 60 ~ 65 DEG C of reactions 6 hours under protection, add polyoxyethylene glycol, be warming up to 90 ~ 95 DEG C of reactions 8 hours, reaction solution poured into precipitating discharging in distilled water, filter, vacuum-drying obtains perylene diimide urethane liquid crystal; Qu perylene diimide urethane liquid crystal is dissolved in chloroform, adds Graphene, supersound process 2 ~ 3 hours, suction filtration, chloroform, vacuum-drying get perylene diimide urethane liquid crystal non-covalent modification Graphene.The inventive method has that raw material sources are wide, technique is simple, price is low, pollute the advantages such as little.
Description
Technical field
The invention belongs to field of high polymer material modification, particularly relate to the preparation method of Yi Zhong perylene diimide urethane liquid crystal non-covalent modification Graphene.
Background technology
Epoxy resin (EP) has chemical resistance, electrical insulating property, bonding force are strong, good stability and the premium properties such as shrinking percentage is little, and it is with low cost, be made up of and the advantage such as processing means flexible formula again, being widely used in the fields such as tackiness agent, coating, potting compound, structured material and fibre reinforced composites, is one of most widely used matrix resin in polymer matrix composite.But because the cross linking of epoxy resin density after solidification is high, internal stress is large, and thus there is the shortcomings such as matter is crisp, resistance to fatigue is poor, thermotolerance is low, be difficult to the requirement meeting modern high technology, the application in high-tech area is subject to certain restrictions.Therefore, utilize Graphene, liquid crystalline cpd and nano material etc. to its enhancing modified, widen its Application Areas, become the study hotspot of current epoxy resin composite material.
Graphene is by a kind of carbonaceous novel material of the individual layer bi-dimensional cellular shape crystalline network of the tightly packed one-tenth of carbon atom, have that the specific surface area of super large, π-pi-conjugated structure, stable chemical nature, mechanical strength are high, electricity and thermal property excellent etc.Research finds, its Young's modulus is 1100GPa, and breaking tenacity reaches 130GPa, far away higher than the intensity of iron and steel, is considered to nano material thin, the hardest in the world at present.
Perylene diimide compounds has good light, heat, chemical stability, is the photoelectric functional material of a class excellent performance, is widely used in liquid-crystal display, electroluminescent device, photodiode, photovoltaic cell and field-effect transistor etc.
Thermotropic urethane liquid crystalline cpd is a kind of novel high performance polymer material, there is the features such as modulus is high, intensity is high, self-enhancement, under liquid crystal state, present the over-all properties that distinctive easy mobility, excellent thermostability, dimensional stability etc. are excellent.
Li Shanrong etc. report patent of invention " a kind of method of biphenyl thermotropic liquid crystal grafting compounds graphene oxide " (ZL201210062490.9), utilize biphenyl type liquid crystalline cpd grafting and modifying graphene oxide, and use it for modified epoxy.In addition, Li Shanrong etc. there was reported publication " end group is containing the method for epoxy group(ing) thermotropic liquid crystal grafting compounds graphene oxide " (CN102766265A), the thermotropic liquid crystal compound utilizing end group to contain epoxide group carries out graft reaction to graphene oxide, obtain end group containing epoxy group(ing) thermotropic liquid crystal grafted graphene oxide compound, and use it for modified epoxy.Research shows: a small amount of liquid crystal modified graphene oxide can the toughness of raising epoxy resin by a relatively large margin, modulus and thermotolerance.
In above-mentioned research, all with liquid crystal, graft modification is carried out to graphene oxide, Er Yi perylene acid anhydride is that Yuan expects to have no bibliographical information at present by Bei perylene diimide urethane liquid crystal non-covalent modification Graphene processed.
Summary of the invention
The object of this invention is to provide the preparation method of Yi Zhong perylene diimide urethane liquid crystal non-covalent modification Graphene.
Concrete steps are:
(1) 0.5 ~ 1 Ke perylene acid anhydride is joined in 30 ~ 40 milliliters of N-Methyl pyrrolidone, add 0.1 ~ 0.3 gram of zinc acetate again and be warming up to 150 ~ 160 DEG C, then stirring and dissolving adds 0.2 ~ 0.6 gram of diglycolamine, isothermal reaction 12 hours, after question response terminates, gained reaction solution is poured into precipitating discharging in dehydrated alcohol, filter, vacuum-drying, obtained Duan Qiang Ji perylene diimide.
(2) the Duan Qiang Ji perylene diimide getting 0.2 ~ 0.5 gram of step (1) obtained is dissolved in 20 ~ 40 milliliters of DMFs, then adds 0.09 ~ 0.2 gram of hexamethylene diisocyanate and 0.02 ~ 0.05 gram of organotin catalysts, at N
2be warming up to 60 ~ 65 DEG C of reactions 6 hours under protection, then add 0.1 ~ 0.3 gram of polyoxyethylene glycol, be warming up to 90 ~ 95 DEG C and continue reaction 8 hours; after reaction terminates, gained reaction solution is poured into precipitating discharging in distilled water, filter; vacuum-drying, get perylene diimide urethane liquid crystal processed.
(3) getting the obtained perylene diimide urethane liquid crystal of 0.2 ~ 0.5 gram of step (2) is dissolved in 20 ~ 40 milliliters of chloroforms, add 0.2 ~ 0.5 gram of Graphene again, then supersound process 2 ~ 3 hours, ultrasonic end after product suction filtration, and with chloroform, vacuum-drying, i.e. get perylene diimide urethane liquid crystal non-covalent modification Graphene processed.
Described organotin catalysts is one or more in tin dilaurate diisobutyl tin, stannous octoate and dibutyltin diacetate.
Described polyoxyethylene glycol is the one in polyoxyethylene glycol-200, PEG-4000, polyoxyethylene glycol-600 and PEG-8 00.
The inventive method has the following advantages:
(1) raw material sources are extensive, and relative low price, environmental pollution is little.
(2) synthesis technique is comparatively simple, is easy to be applied to industrial production.
(3) perylene diimide urethane liquid crystal non-covalent modification Graphene prepared by is used for modified epoxy, the chemiluminescence of urethane liquid crystal and Graphene can be realized, and can be uniformly dispersed in resin matrix, to resin, there is obvious toughening modifying effect.
Embodiment
Main raw material: perylene acid anhydride (analytical pure) that following examples are used, Graphene (technical grade), N-Methyl pyrrolidone (NMP, analytical pure), zinc acetate (analytical pure), diglycolamine (analytical pure), dehydrated alcohol (analytical pure), N, dinethylformamide (DMF, analytical pure), hexamethylene diisocyanate (analytical pure), tin dilaurate diisobutyl tin (analytical pure), polyoxyethylene glycol-200 (analytical pure), chloroform (analytical pure), epoxy resin (epoxy E-44, technical grade), 4, 4 '-diaminodiphenylsulfone(DDS) (DDS, technical grade).
Embodiment 1:
(1) 0.5 Ke perylene acid anhydride is joined in 30 milliliters of N-Methyl pyrrolidone, add 0.13 gram of zinc acetate again and be warming up to 160 DEG C, then stirring and dissolving adds 0.268 gram of diglycolamine, isothermal reaction 12 hours, after question response terminates, gained reaction solution is poured into precipitating discharging in dehydrated alcohol, filter, vacuum-drying, obtained Duan Qiang Ji perylene diimide.
(2) the Duan Qiang Ji perylene diimide getting 0.25 gram of step (1) obtained is dissolved in 20 milliliters of DMFs, then adds 0.093 gram of hexamethylene diisocyanate and 0.02 gram of catalyst dibutyltin cinnamic acid diisobutyl tin, at N
2be warming up to 60 DEG C of reactions 6 hours under protection, then add 0.11 gram of polyoxyethylene glycol-200, be warming up to 90 DEG C and continue reaction 8 hours, after reaction terminates, gained reaction solution is poured into precipitating discharging in distilled water, filter, vacuum-drying, makes to obtain perylene diimide urethane liquid crystal.
(3) getting the obtained perylene diimide urethane liquid crystal of 0.3 gram of step (2) is dissolved in 30 milliliters of chloroforms, add 0.3 gram of Graphene again, then supersound process 2 hours, ultrasonic end after product suction filtration, and with chloroform, vacuum-drying, i.e. get perylene diimide urethane liquid crystal non-covalent modification Graphene processed.
Get 0.026 gram of the present embodiment to obtain perylene diimide urethane liquid crystal non-covalent modification Graphene and join in 26 grams of epoxy resin-bases, decompression is bled, add 7.8 grams of DDS solidifying agent again, mixing is poured into after melting and is scribbled in the steel die of estersil, in 120 DEG C/2 hours+160 DEG C/2 hours+180 DEG C/2 little curing moldings at present, make to obtain perylene diimide urethane liquid crystal non-covalent modification Graphene modified epoxy resin composite.
Obtain the modified epoxy resin of perylene diimide urethane liquid crystal non-covalent modification Graphene (consumption is only the 0.1wt% of epoxy resin) through the present embodiment, its shock strength is by the 17.9kJ/m of pure epoxy resin
2bring up to 22.6kJ/m
2, improve 26.3%, tensile strength improves 13.4%, and flexural strength increases by 35.4%, and heat decomposition temperature improves 28 DEG C than pure epoxy resin.
Embodiment 2:
(1) 0.8 Ke perylene acid anhydride is joined in 32 milliliters of N-Methyl pyrrolidone, add 0.2 gram of zinc acetate again and be warming up to 160 DEG C, then stirring and dissolving adds 0.429 gram of diglycolamine, isothermal reaction 12 hours, after question response terminates, gained reaction solution is poured into precipitating discharging in dehydrated alcohol, filter, vacuum-drying, obtained Duan Qiang Ji perylene diimide.
(2) the Duan Qiang Ji perylene diimide getting 0.4 gram of step (1) obtained is dissolved in 32 milliliters of DMFs, then adds 0.148 gram of hexamethylene diisocyanate and 0.04 gram of catalyst dibutyltin cinnamic acid diisobutyl tin, at N
2be warming up to 60 DEG C of reactions 6 hours under protection, then add 0.176 gram of polyoxyethylene glycol-200, be warming up to 92 DEG C and continue reaction 8 hours; after reaction terminates, gained reaction solution is poured into precipitating discharging in distilled water, filter; vacuum-drying, get perylene diimide urethane liquid crystal processed.
(3) getting the obtained perylene diimide urethane liquid crystal of 0.4 gram of step (2) is dissolved in 32 milliliters of chloroforms, add 0.4 gram of Graphene again, then supersound process 2.5 hours, ultrasonic end after product suction filtration, and with chloroform, vacuum-drying, i.e. get perylene diimide urethane liquid crystal non-covalent modification Graphene processed.
Get 0.13 gram of the present embodiment to obtain perylene diimide urethane liquid crystal non-covalent modification Graphene and join in 26 grams of epoxy resin-bases, decompression is bled, add 7.8 grams of DDS solidifying agent again, mixing is poured into after melting and is scribbled in the steel die of estersil, in 120 DEG C/2 hours+160 DEG C/2 hours+180 DEG C/2 little curing moldings at present, make to obtain perylene diimide urethane liquid crystal non-covalent modification Graphene modified epoxy resin composite.
Obtain the modified epoxy resin of perylene diimide urethane liquid crystal non-covalent modification Graphene (consumption is only the 0.5wt% of epoxy resin) through the present embodiment, its shock strength is by the 17.9kJ/m of pure epoxy resin
2bring up to 27.5kJ/m
2, improve 53.6%, tensile strength improves 23%, and flexural strength increases by 44.8%, and heat decomposition temperature improves 31 DEG C than pure epoxy resin.
Embodiment 3:
(1) 1 Ke perylene acid anhydride is joined in 40 milliliters of N-Methyl pyrrolidone, add 0.25 gram of zinc acetate again and be warming up to 160 DEG C, then stirring and dissolving adds 0.536 gram of diglycolamine, isothermal reaction 12 hours, after question response terminates, gained reaction solution is poured into precipitating discharging in dehydrated alcohol, filter, vacuum-drying, obtained Duan Qiang Ji perylene diimide.
(2) the Duan Qiang Ji perylene diimide getting 0.5 gram of step (1) obtained is dissolved in 40 milliliters of DMFs, then adds 0.185 gram of hexamethylene diisocyanate and 0.05 gram of catalyst dibutyltin cinnamic acid diisobutyl tin, at N
2be warming up to 63 DEG C of reactions 6 hours under protection, then add 0.22 gram of polyoxyethylene glycol-200, be warming up to 94 DEG C and continue reaction 8 hours, after reaction terminates, gained reaction solution is poured into precipitating discharging in distilled water, filter, vacuum-drying, makes to obtain perylene diimide urethane liquid crystal.
(3) getting the obtained perylene diimide urethane liquid crystal of 0.5 gram of step (2) is dissolved in 32 milliliters of chloroforms, add 0.5 gram of Graphene again, then supersound process 2.5 hours, ultrasonic end after product suction filtration, and with chloroform, vacuum-drying, i.e. get perylene diimide urethane liquid crystal non-covalent modification Graphene processed.
Get 0.182 gram of the present embodiment to obtain perylene diimide urethane liquid crystal non-covalent modification Graphene and join in 26 grams of epoxy resin-bases, decompression is bled, add 7.8 grams of DDS solidifying agent again, mixing is poured into after melting and is scribbled in the steel die of estersil, in 140 DEG C/2 hours+160 DEG C/2 hours+180 DEG C/2 little curing moldings at present, make to obtain perylene diimide urethane liquid crystal non-covalent modification Graphene modified epoxy resin composite.
Obtain the modified epoxy resin of perylene diimide urethane liquid crystal non-covalent modification Graphene (consumption is only the 0.7wt% of epoxy resin) through the present embodiment, its shock strength is by the 17.9kJ/m of pure epoxy resin
2bring up to 30.2kJ/m
2, improve 68.8%, tensile strength improves 34%, and flexural strength increases by 48.5%, and heat decomposition temperature improves 40 DEG C than pure epoxy resin.
Claims (1)
1. the preparation method of Yi Zhong perylene diimide urethane liquid crystal non-covalent modification Graphene, is characterized in that concrete steps are:
(1) 0.5 ~ 1 Ke perylene acid anhydride is joined in 30 ~ 40 milliliters of N-Methyl pyrrolidone, add 0.1 ~ 0.3 gram of zinc acetate again and be warming up to 150 ~ 160 DEG C, then stirring and dissolving adds 0.2 ~ 0.6 gram of diglycolamine, isothermal reaction 12 hours, after question response terminates, gained reaction solution is poured into precipitating discharging in dehydrated alcohol, filter, vacuum-drying, obtained Duan Qiang Ji perylene diimide;
(2) the Duan Qiang Ji perylene diimide getting 0.2 ~ 0.5 gram of step (1) obtained is dissolved in 20 ~ 40 milliliters of DMFs, then adds 0.09 ~ 0.2 gram of hexamethylene diisocyanate and 0.02 ~ 0.05 gram of organotin catalysts, at N
2be warming up to 60 ~ 65 DEG C of reactions 6 hours under protection, then add 0.1 ~ 0.3 gram of polyoxyethylene glycol, be warming up to 90 ~ 95 DEG C and continue reaction 8 hours, after reaction terminates, gained reaction solution is poured into precipitating discharging in distilled water, filter, vacuum-drying, get perylene diimide urethane liquid crystal processed;
(3) getting the obtained perylene diimide urethane liquid crystal of 0.2 ~ 0.5 gram of step (2) is dissolved in 20 ~ 40 milliliters of chloroforms, add 0.2 ~ 0.5 gram of Graphene again, then supersound process 2 ~ 3 hours, ultrasonic end after product suction filtration, and with chloroform, vacuum-drying, i.e. get perylene diimide urethane liquid crystal non-covalent modification Graphene processed;
Described organotin catalysts is one or more in tin dilaurate diisobutyl tin, stannous octoate and dibutyltin diacetate;
Described polyoxyethylene glycol is the one in polyoxyethylene glycol-200, PEG-4000, polyoxyethylene glycol-600 and PEG-8 00.
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Effective date of registration: 20190305 Address after: 312000 West Side of Shangma Bay Village East Ring Line, Fuquan Street, Keqiao District, Shaoxing City, Zhejiang Province Patentee after: Shaoxing Guenot SuperLing Lubrication Material Co., Ltd. Address before: No. 12, Jian Gong Road, Guilin, the Guangxi Zhuang Autonomous Region Patentee before: Guilin University of Technology |